Sulfonamides, processes for their preparation, compositions containing said sulfonamides and a method for controlling the growth of vegetation.
Abstract
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45 claims: 1 independent, 44 dependent
- 1PATENT CLAIMS:10 1, means for controlling unwanted vegetation, characterized in that it contains as active ingredient a compound of general formula - 157 No.371668 or an agriculturally suitable salt of this compound in which each symbol has the following meanings: Q = 0, S or NR;where 5 if Q = 0, R = H, Na, C, -O-alkyl, C 2 -C, alkyl substituted by CI, C 2 Alkyl substituted by OC 2 H e , OCH 2 CH 2 C1, OCH 2 CH 2 OCH 2 CH 2 C1, OC s H 5 or Ο, Η,, CH 2 C 6 H S , 4-C1-C 6 H "CH 2 , C 5 C, -Cycloalkyl optionally substituted by CH, C, -C, O bicycloalkyl, C, -C 6 Alkenyl, -, 3-tetrahydrofuranyl or 1-adamantyl;10 if Q = S, R = O, -C, -alkyl, cyclohexyl or benzyl;if Q = NR S . R = C, -C, 2 Alkyl, C, -C, alkenyl, OCH,, C, -C 6 -Cycloalkyl, CH 2 C 6 H S or CHC 6 H 5 ;CH, 15 R e = H, CH, or C 2 H 5 ;or R and R 6 taken together - (CH 2 ) 4 -, ~ (CH 2 ) 5 - or -CH 2 CH 2 0CH 2 CH 2 ~;provided that R «OCH,, R e = CH 3 ;and R and R 6 have a total of <13 carbon atoms;R 2 = H, CI, F, NH 2 or NO 2 ;R, = H or CI;R = H or CH ,;CH. in which N < / o \ - \ O> - <o \ O / N-- 7 n-ς N > or CH, - <o \ ^ / N- 7 -CH;CH, if R, N- ( N < X = H, CI, CH, or OCH;and Y = H, CI, CH,, C, -C 2 Alkoxy, C 2 ~C, alkyl substituted by OCH, or QC "Η, OCH, CF, OCH, C0, CH ,, OCHCO 2 CH 3 , SCH CH 0C Η, N or SCN;CH. if - N- 7 - 158 No.371668 X = CI, CH 3 or OCH 3 ;and CH OCH, CH, 0 , N 3 or SCH 2 C0 2 CH 3 ;provided that when Ί> contains 4 C atoms, R_ contains <4 C atoms;when X = CI, Y = CI;and when X and Y both contain = H, R £ 4 C atoms.
- 99th Composition according to Claim 8, containing a compound of the formula (I) in which R 2 = H or CI.
- 1212th Composition according to Claim 9, containing a compound of the formula (I) in which X;wherein CH. - 159 Nr.371668 0CH 2 CH = CH 2 ;or N (CH 3 ) 2 ,
- 1620th Composition according to Claim 17, comprising a compound of the formula (I) in which Q = O, and R = Cj-C ^ -alkyl ,. C 2 -C 3 Alkyl substituted by CI or C 3 -C ^ alkenyl. 1 CH 3
Independent claims4
4,337 paragraphs in 228 sections, as filed
© Start of patent duration: 1982 12 15 Longest possible duration:
§ Issued on: 1983 07 25
Inventor:
3959/79 (US) 1978 05 30 CLAIM (US) 1978 11 30 CLAIM (US) 1979 03 01 CLAIM (US) 1979 04 13 CLAIMED © Dependency:
© Pamphlets considered to delineate the prior art:
ΠΛΑ ΤΙ Π
- 2 No.371668
The invention relates to agents for controlling undesired vegetation containing as active ingredient new N- (heterocyclicaminocarbonyl) arylsulfonamides in which the aryl radical is substituted by a carboxyl radical, its ester, thioester or amide.
NL-PS No. 121788 discloses the preparation of compounds of the following formula and their use as general and selective herbicides:
<img file="AT371668B_D0001.tif" />
wherein Rj and R<sub>2</sub> independently of one another alkyl having 1 to 4 carbon atoms and R<sub>3</sub> and R "independently of one another may be hydrogen, chlorine or alkyl having 1 to 4 carbon atoms. U.S. Patent No. 3,637,366 discloses compounds of the formula
RjHN./q \.
\ A /
-so<sub>2</sub>NHR<sub>2</sub> wherein
Rj is hydrogen or low. saturated aliphatic acyl and
R<sub>2</sub> Is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbampyl. The disclosed compounds are said to enable the control of crabgrass, cress, endive, clover and Poa annua.
FR-PS No. 1,468,747 discloses the following p-substituted phenylsulfonamides as antidiabetic agents:
z \ _
A_
SO NH-C-NHworin R = halogen, CF<sub>s</sub> or alkyl.
Chem. Ab. 53, 18052 g [1959] discloses a number of sulfonamides, including uracil derivatives and those of the formula wherein R = butyl, phenyl or
<img file="AT371668B_D0002.tif" />
II so<sub>2</sub>nhcnhr
R<sub>3</sub> = Hydrogen or methyl.
In tests for hypoglycemic activity in rats (oral doses of 25 mg / 100 g), the compounds in which R is butyl and phenyl proved most effective. The others were weaker or inactive.
Wojciechowski, J. Acta. Polon. Pharm 19, p. 121 to 125 [1962] (Chem. Ab., 59, 1633 e) describe the synthesis of N- [(2,6-dimethoxypyrimidin-4-yl) aminocarbonyl] -4-methylphenol sulfone 30 amide:
- 3 Nr.371668
Because of the similarity with a known compound, the authors suggest that the above compound could have hypoglycemic activity.
Substituted pyrimidinyl-sulfonylureas of the following formula, which may also be para-substituted in the phenyl ring, are described in Farmco Ed. Sci., 12, 586 [1957] (Chem. Ab., 53, 18052 g [1959])
CH
Λ.
J
SO.NH-C-NH./
CH, • SO, NH-C-NH \.
och<sub>3</sub>
OCH,
CH, wherein R = H or CH<sub>3</sub>, open-minded.
The occurrence of undesired vegetation causes considerable damage to useful plants, especially agricultural products such as cotton, rice, corn, wheat and the like. The current explosive population growth and associated scarcity of food and fiber commodities around the world are driving performance improvements in crop production. Preventing or reducing the loss of part of such valuable crops by killing off or inhibiting the growth of unwanted vegetation is one way to improve performance. A wide variety of materials suitable for killing or inhibiting growth of unwanted vegetation is available; such materials are commonly referred to as herbicides. However, there is still a need for even more effective herbicides.
The compositions according to the invention contain as active ingredient new compounds of the formula (I) and / or their agriculturally suitable salts, eg salts with Na, K, alkylammonium, trichloroacetic acid. These agents are useful as general or selective pre- or post-emergence herbicides (pre- or post-emergent emergence herbicides) and as plant growth regulants,
CI)
II
<img file="AT371668B_D0003.tif" />
in which the individual symbols have the following meanings:
Q = 0, S or NR<sub>e</sub>; where Q = 0,
B = H, Na, C<sub>3</sub>-C<sub>10</sub> Alkyl, C<sub>2</sub>-C<sub>3</sub>Alkyl substituted by CI, C<sub>2</sub>Alkyl substituted by OC<sub>2</sub>H<sub>5</sub>, OCH<sub>2</sub>CH<sub>2</sub>C1, OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub> CH<sub>2</sub>C1, OC<sub>6</sub>H<sub>5</sub> or C<sub>e</sub>H<sub>s</sub>, CH<sub>2</sub>C<sub>6</sub>H<sub>S</sub>, 4-C1-CH, CH<sub>2</sub>, C <sub>5</sub> -C <sub>B</sub> -Cycloalkyl optionally substituted by CH<sub>3</sub>, Ο<sub>7</sub>-Ο<sub>Ι3</sub> Bicycloalkyl, C<sub>3</sub>-C<sub>6</sub>-Al4
No.371668 if Q = S,
R = Cj-C, -alkyl, cyclohexyl or benzyl;
if Q = NR <sub>5</sub>.
R = Cj-C <sub>12</sub>Alkyl, C<sub>3</sub>-C "alkenyl, OCH<sub>3</sub>, C, -C<sub>6</sub>-Cycloalkyl, CH<sub>2</sub>C<sub>6</sub>H<sub>5</sub> or CHC<sub>6</sub>H<sub>5</sub>;
CH, kenyl,
-O
3-tetrahydrofuranyl or 1-adamantyl;
R and R<sub>6</sub> taken together - (CH<sub>2</sub>) ^ -, - (CH<sub>2</sub>)<sub>5</sub>- or -CH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>-; provided that when R = OCH ,, R<sub>6</sub> = CH<sub>3</sub> ; and R and R have a total of 13 lb carbon atoms;
R<sub>2</sub> = H, CI, F, NH or NO;
<img file="AT371668B_D0004.tif" />
- <o>
N- (
CH.
./
Λ /
λ- or or
Ν "N,
- <O>
N- (
CH.
CH,
CH where R<sub>t</sub> -
<img file="AT371668B_D0005.tif" />
X = H, CI, CH<sub>3</sub> or OCH<sub>3</sub>; and
Y = H, CI, CH<sub>3</sub> , C <sub>2</sub> -C <sub>2</sub> Alkoxy, C<sub>2</sub>~ C<sub>3</sub> Alkyl substituted by OCH<sub>3</sub> or OC<sub>2</sub>H<sub>5</sub> ; OCH CF, OCH CO CH, OCHCO "CH, SCH CH OC Η, N or SCN;
3 2 2 3 | 23 '222<sub>5</sub>'3
CH.
if R.
<
\O/
N <
X = CI, CH<sub>3</sub> or OCH<sub>3</sub>; and
Y = CI, CH<sub>3</sub>, CH<sub>2</sub>0CH<sub>3</sub>, CH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub> , C<sub>3</sub>-C, alkoxy, C <sub>2</sub>-C <sub>3</sub>Alkoxy substituted by OCH, or OC.H ,; OCH, CH = CH. , OCH.C ξ CH, OCH CH CI, OCH CH CN, OCH CF, □ t □ & lt; 22 2 2 2 3 och<sub>2</sub>cci<sub>3</sub>, och<sub>2</sub>co<sub>2</sub>ch<sub>3</sub>, och<sub>2</sub>co<sub>2</sub>c<sub>2</sub>H<sub>s</sub>, ochco<sub>2</sub>ch<sub>3</sub>, n (ch<sub>3</sub>)<sub>2</sub>, n<sub>3</sub>, n<sub>2</sub>cn,, ~
N<sup>Z</sup>
2 2 5 '* 3' <sub>Γ</sub>-2CH.
och<sub>3</sub> ch<sub>3</sub> provided that, if Y contains 4 C atoms, R <4 contains C atom; when X = CI, Y = CI; and when X and Y both contain H, R 14 carbon atoms.
The following groups of compounds of the formula (I) are preferred:
- 5 Nr.371668
1. Compounds of the general formula (I) in which R<sub>s</sub> = H, and that bound to Q carbon atom of R is also bound to at least one H.
Second Compounds of preferred group 1) in which R<sub>2</sub> = H, CI, F, -NO<sub>2</sub> or -NH<sub>2</sub> and R, = H and p-position to the sulfonyl group.
Third Compounds of preferred group 2) in which Q = 0 or S and R (when Q = 0) = -O, -O, -alkyl, C, -C, -alkenyl, C<sub>2</sub>-C<sub>3</sub>Alkyl substituted by CI; C, -C "alkenyl; C<sub>s</sub>-C, cycloalkyl, optionally substituted by methyl; benzyl; 4-Cl-C<sub>6</sub>H "CH<sub>2</sub>; Tetrahydrofuranyl or \ / \;
and R (when Q = S) = Cj-C, alkyl, cyclohexyl or benzyl.
4th Compounds of the preferred group 2) in which Q = 0 and R = H, Na or 10 -CH<sub>2</sub>CH<sub>2</sub>OC<sub>2</sub>H<sub>s</sub>,
5th Compounds of preferred group 2) in which Q = -NR, - and R = O, -O, -alkyl, C, -C "-alkenyl, C, -C, -cycloalkyl, -OCH ,; CH<sub>2</sub>C, H, or CHC, H; R, = H, CH, or C<sub>2</sub>H, or R,
CH, and R taken together - (CH<sub>2</sub>) "-, - (CH<sub>2</sub>)<sub>S</sub>- or -CH<sub>2</sub>CH<sub>2</sub>OCH<sub>2</sub>CH<sub>2</sub>- form.
6th Compounds of Preferred Group 2) in which X = CH, or OCH, and Y = H, 15 C, -C<sub>ä</sub>Alkyl substituted by -OCH, or -OC<sub>2</sub>H<sub>5</sub>; -OCH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub>, -OCHCO<sub>2</sub>CH, or -0CH<sub>2</sub>CH<sub>2</sub>C0<sub>2</sub>CH ,.
CH<sub>S</sub>
7th Compounds of preferred group 6) in which -QR is defined as in group 4).
8th. Compounds of preferred group 6) in which -QR is defined as in group S).
9th Preferred group 6) compounds in which -QR is defined as in group 6).
10th Compounds of preferred groups 7, 8 or 9) in which R<sub>2</sub> = H or CI.
11th Compounds of preferred group 10) in which Q = 0 or S and R (when Q = O) = C 1 -C 4 alkyl, C 1 -C 6 alkenyl; C<sub>2</sub>-C, alkyl optionally substituted by CI; C, -C, cycloalkyl; Cyclohexenyl, cyclohexyl substituted by 1 to 3 -CH ,; Benzyl or 4-Cl-C, H "CH<sub>2</sub>,
12th Compounds of preferred group 10) in which Q = O; and R = H, Na or C<sub>2</sub>alkyl,
13th Compounds of preferred group 10) in which Q = -NR, -; and R,
C<sub>2</sub>H<sub>5</sub> ; and R = C, -C "alkyl; C, -C "alkenyl; C<sub>5</sub>-C, cycloalkyl or benzyl; or R and R, taken together - (CH<sub>2</sub>) "- or -CH<sub>2</sub> CH<sub>2</sub> 0CH<sub>2</sub> CH<sub>2</sub> - form.
14th Compounds of the preferred group 10 in which R, =, N- \ <sup>Z</sup>O>
N30 in which
X = CI, CH, or OCH;
Y = CH ,, -CH <sub>2</sub> OCH,, -CH<sub>2</sub>0CH<sub>2</sub>CH,, -OCH<sub>2</sub>CO<sub>2</sub>CH<sub>3</sub>, -OCH-CO <sub>2</sub> CH, -O- (C, -C, -alkyl) or CH,
0CH<sub>2</sub>CH = CH<sub>2</sub>; or N (CH,)<sub>2</sub> ,
15th Compounds of preferred group 14) in which QR is defined as in 11).
16th Compounds of preferred group 14) in which QR is defined as in 12).
17th Compounds of preferred group 14) in which QR is defined as in 13).
18th Compounds of preferred groups 15, 16 or 17) in which R<sub>2</sub> and R, both are hydrogen.
19th Compounds of Preferred Group 18) in which Q = O and R = C, -C "alkyl, 40C, -C" alkenyl, C<sub>2</sub>-C, alkyl substituted by CI; -CH<sub>2</sub>CH<sub>2</sub>OC<sub>2</sub>H,.
- 6 No.371668
20th Compounds of preferred group 18) in which Q = S and R = Cj-C "alkyl.
21st Compounds of preferred group 18) in which Q = -NR<sub>6</sub> and R = C, -C "alkyl, C <sub>3</sub>-C "alkenyl, -CH<sub>2</sub>CH<sub>2</sub>0-C<sub>2</sub>H<sub>s</sub> and R<sub>s</sub> = H or CH<sub>3</sub> , or R and R<sub>6</sub> taken together -iCH<sub>2</sub>U or -CH<sub>2</sub>CH<sub>2</sub>0CH<sub>2</sub>CH<sub>2</sub>- form.
22nd Compounds of preferred group 18) in which X = CH<sub>3</sub> or -OCH<sub>3</sub> and Y = CH<sub>3</sub> .
-OCH<sub>3</sub>.
OC <sub>2</sub> H <sub>s</sub>, -OCH <sub>2</sub> GO <sub>2</sub>-CH <sub>3</sub>, -OCHCH <sub>2</sub> CO <sub>2</sub>-CH <sub>2</sub> OCH<sub>3</sub> ,
CH,
Group 22) compounds where -QR is defined as in 19). Group 22) connections where QR is defined as in 20).
23rd
24th
25th Group 22) connections where QR is defined as in 21).
Especially preferred are:
N- [(4,6-dimethylpyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide N- [(4,6-dimethyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide N - [(4-methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzolsulfonamid
N - [(4,6-dimethoxypyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide
N - [(4,6-dimethoxy-l, 3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide
N - [(4,6-dimethoxy-l, 3,5-triazin-2-yl) -aminocarbonyl] -2- (isopropoxycarbonyl) -benzenesulfonamide
N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2- (isopropoxycarbonyl; benzenesulfonamide
N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -2- (2-chloroethoxycarbonyl) -benzenesulfonamide
N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2- (2-chloroethoxycarbonyl) -benzenesulfonamide
N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-propoxycarbonylbenzenesulfonamide 25 N - [(4-Methoxy-6-methylpyrimidin-2-yl) -aminocarhonyl ] -2- (2-chloroethoxycarbonyl) benzenesulfonamide
N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2- (2-phenyl-1-methylethoxycarbonyl) -benzenesulfonamide
N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2- [2- {2-chloroethoxy) -ethoxycarboxylic 30-nyl] -benzenesulfonamide
N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2- (2-ethoxyethoxycarbonyl) -benzenesulfonamide
N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-allyloxycarbonylbenzenesulfonamide N- [(4-methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2-dimethylcarbamoyl-benzenesulfonamide <sup>35</sup> N- ζ {[4-methyl-6- (1-methoxycarbonylethoxy) pyrimidin-2-yl] aminocarbonyl)) -2-methoxycarbonylbenzenesulfonamide
N - <{[4-Methyl-6- (1-methoxycarbonyl-ethoxy) -l, 3,5-triazin-2-yl] -aminocarbonyl)} -2-methoxycarbonylbenzenesulfonamide
N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methylthiocarbonylbenzenesulfone 4 ° amide
N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-isopropylthiocarbonylbenzenesulfonamide
N - [(4-methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2-isopropylthiocarbonylbenzenesulfonamide N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2- (2-methylpropoxycarbonyl) benzene<sup>45</sup> sulfonamide
N - [(4-Methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2- (4-morpholinylaminocarbonyl) -benzenesulfonamide
N- [(4,6-Dimethoxypyrimidin-2-yl) -aminocarbonyl] -2- (1-pyrrolidinylcarbonyl) -benzenesulfonamide N- [(4,6-Dimethoxypyrimidin-2-yl) -aminocarbonyl] -2- (allyloxycarbonyl) benzenesulfonamide.
<sup>50</sup> syntheses
Many compounds of formula (I) are converted by reaction as shown in equation 3
Nr.371668
- 7 a suitably substituted o-carbonylbenzenesulfonyl isocyanate with a suitable
Aminopyrimidine or aminotriazine produced. These compounds of formula (I) may be used in others
Compounds of formula (I) are converted, as shown in the following equations. Thus, o-carbonyl phenolsulfonyl isocyanates are important intermediates for the preparation of compounds of formula (I). Therefore, their synthesis is described in Equation 1. Equation i
<img file="AT371668B_D0006.tif" />
DABCO nC ^ H, NCO
xylene
reflux
<img file="AT371668B_D0007.tif" />
(Π)
A mixture of the subject sulfonamide, eg, an o-alkoxycarbonylbenzenesulfonamide (Ha) such as the methyl ester, a known compound of an alkyl isocyanate such as butyl isocyanate, and a catalytic amount of 1,4-diaza [2,2,2] bicyclooctane (DABCO) in xylene or another inert solvent of sufficiently high boiling point (eg 135 ° C) is heated to about 135 ° C. Phosgene is added to the mixture until it is in excess, which is reflected in a drop in boiling point. (The mixture is heated further to drive off the excess phosgene). After cooling the mixture and filtering off a small amount of insoluble by-products, the solvent and the alkyl isocyanate are distilled off in vacuo to give a residue of the crude sulfonyl isocyanate (II).
In equation 1 mean:
- Q = 0
R = C<sub>J</sub>-C<sub>M</sub> alkyl; G<sub>3</sub>-C<sub>6</sub>alkenyl; Cj-C, alkyl substituted by CI; C<sub>2</sub>Alkyl substituted 20 by OC <sub>2</sub> H <sub>5</sub> , OC <sub>s</sub> H <sub>5</sub> or OCH <sub>2</sub> CH <sub>2</sub> CI; C<sub>5</sub> -G <sub>6</sub> -Cycloalkyl, optionally substituted by CH <sub>3</sub>;
R<sub>2</sub> = H, CI, F or -N0<sub>2</sub>.
R<sub>3</sub> = H or CI.
The method of synthesis chosen for the preparation of the compounds of the formula (I) depends largely on the substituents R. As shown in equation 3, compounds of formula (I) wherein Q, R, R<sub>2</sub> and R<sub>3</sub> as defined for Equation 1, suitably prepared by reacting a suitably substituted carbonylbenzenesulfonyl isocyanate of the formula (IIb) with a suitably substituted aminopyrimidine or aminotriazine of the formula (III):
Equation 3
<img file="AT371668B_D0008.tif" />
<img file="AT371668B_D0009.tif" />
The reaction of Equation 3 is best carried out in an inert aprotic solvent such as methylene chloride, tetrahydrofuran or acetonitrile at ambient pressure and temperature. The way of adding is not critical; however, it is often convenient to add the sulfonyl isocyanate to a stirred suspension of the amine (III). Since these isocyanates are liquid, low melting solids or readily soluble in solvents such as those listed above, the addition can be readily made in a controlled manner.
The reaction is generally exothermic. In some cases, the desired product is soluble in the warm reaction medium and crystallizes on cooling in a pure form. Other products which are soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as 1-chlorobutane or ethyl ether and filtration.
As shown in equation 4, compounds of formula (I) wherein Q is O, S or -N-, R may be as defined for equation 1 and R<sub>u</sub> Methyl means by methylation of
R
Salts (IV) in which M is a sodium cation, are prepared:
Equation 4
<img file="AT371668B_D0010.tif" />
<img file="AT371668B_D0011.tif" />
where X is an anion and n is an integer corresponding to the valence of X.
The reaction of Equation 4 is best carried out in an aprotic organic solvent such as tetrahydrofuran, dimethylformamide or dimethylacetamide at ambient pressure and temperature. Methylating agents (V) such as dimethyl sulfate or methyl iodide may be used. The desired product can be isolated by pouring the reaction mixture into water and filtering off the precipitated solid.
As shown in Equation 5, compounds of formula (Ic) wherein Q is O, S or
-N- and R is as defined for Equation 4, also be prepared by reaction of a suitably substituted sulfonyl-N-methylcarbamyl chloride of the formula or aminotriazine of the formula (III):
Equation 5 (VI) with a suitable aminopyrimidine
<img file="AT371668B_D0012.tif" />
(III)
<img file="AT371668B_D0013.tif" />
(IC)
- 9 Nr.371668
The preparation of ureas such as those of formula (Ic) from amines and carbamoyl chlorides is well known. The reaction can best be carried out by adding equivalent amounts of the chloride (VI) and amine (II) to an organic solvent such as tetrahydrofuran, xylene or methylene chloride in the presence of an acid acceptor such as triethylamine, pyridine or sodium carbonate 5 using a temperature of 20 to 130 ° C be performed. Soluble products can be isolated by filtering off the precipitated salts and concentrating the filtrate. Insoluble products can be filtered off and washed salt-free with water.
The chlorides of the formula (VI) can be prepared by phosphogenation of N-alkyl sulfone amide salts. The sulfonamide salt is added to excess phosgene in an inert organic solvent such as tetrahydrofuran, toluene or xylene, after which, after removal of the excess phosgene, the chloride (VI) can be isolated or reacted in situ with the amine (III).
Compounds of formula (Ie) wherein R = H can be prepared by hydrolysis of esters of formula (Id) wherein R = O, -O, -alkyl. As shown in Equation 6, hydrolysis in aqueous methanol catalyzed by 15% alkali metal gives the alkali metal carboxylate from which the carboxylic acid is obtained by treatment with mineral acids such as HCl:
Equation 6
<img file="AT371668B_D0014.tif" />
The reaction of Equation 6 is best carried out in a solution containing the compound to be hydrolyzed, 2 to 10 parts of methanol, 10 to 50 parts of water and 2 to 10 equivalents of a base such as potassium hydroxide while maintaining a temperature of 30 to 90 ° C performed for 3 to 24 hours. The reaction provides the soluble alkali metal salt of the carboxylic acid which is suitable for the purposes of the invention. The conversion of these salts into the acid form can be easily by addition of strong mineral acids such as hydrochloric or sulfuric acid to the reac<sup>25</sup> Perform tion medium, wherein the desired carboxylic acid precipitates from the solution.
Compounds in which Q = 0 and R = H can be obtained in compounds of the formula (I) in which R is a higher alkyl or substituted hydrocarbyl group, as already explained, by reacting the salts of the parent acid (R = H) with R-halogen, as shown in Equation 6A.
Nr.371668
Equation 6A
<img file="AT371668B_D0015.tif" />
II
MR,
II
<img file="AT371668B_D0016.tif" />
MR
The reaction of Equation 3 is useful when the intermediate R-halo contains an easily replaceable halogen as in the case of substituted or unsubstituted allyl or benzylic halides, α-halonitriles or α-halocarbonyl compounds.
The procedure of Equation 6A is best practiced in inert polar solvents such as
Tetrahydrofuran, acetonitrile or acetone by contacting the appropriately substituted carboxylic acid and a base such as triethylamine or 1,4-diaza [2,2,2] bicyclooctane with the appropriate halide and refluxing the mixture with stirring for 1 to 16 hours.
The reaction mixture may be evaporated to dryness and the residue triturated with water, filtered and washed with water to separate the desired product from the water-soluble salt.
If Q = NR<sub>6</sub> For example, the compounds can be prepared from the esters in which R = Cj-C ^ (preferably C,) by reacting the esters with dialkylaluminum N-alkylamide derivatives according to Equation 7, wherein R, R<sub>lt</sub> R<sub>2</sub>, R<sub>ä</sub> and R<sub>6</sub> as defined earlier.
Equation 7
<img file="AT371668B_D0017.tif" />
Toluene - =>
<sup>R</sup>s
CO-NR
<img file="AT371668B_D0018.tif" />
SOjNHCNH-Rj
cif)
The alkylaminoaluminum intermediates, prepared according to A.Basha, M. Lipton and SW Weinreh, Tetrahedron Leiters 4171 [1977], are mixed with a suspension of the esters in toluene or a similar solvent and the mixture is refluxed for 1 to 6 hours. 11 No.371668 heat. The product can be isolated by evaporation of the solvent toluene, addition of methylene chloride and aqueous hydrochloric acid to decompose the remaining reaction mass and extraction of the desired product with methylene chloride. By evaporating the methylene chloride, the desired product is obtained which is sufficiently pure for the purposes of the invention
Shape.
Compounds of formula (Ild) in which Q = NR<sub>6</sub> and R<sub>t</sub>, R<sub>2</sub>, R<sub>3</sub> and R <as defined earlier in the general formula which are useful as intermediates in Equation 3A are prepared according to Equation 7A:
Equation 7A
CO.CH.
<img file="AT371668B_D0019.tif" />
The conditions described for Equation 7 are suitable for the conversion of the esters of formula (IIc) into the amides (Ild) shown in Equation 7A.
The products of Equation 7A are particularly useful for the preparation of the compounds of Formula (Ia) in which Y is an ester substituent CO<sub>2</sub>(C<sub>l</sub>-C<sub>l (</sub>), in which in equation
3A described way.
When Q = S, these compounds may be selected from the esters of formula (I) in which QR = = C<sub>t</sub>-C ^ alkoxy (preferably Cj), by reacting these esters with the appropriate dialkylaluminum alkylthiolate according to Equation 8:
Equation 8
<img file="AT371668B_D0020.tif" />
<img file="AT371668B_D0021.tif" />
The al uminiumthiolat Z wischen ver bin fertilize can be prepared according to SW Weinreb, Journal of Organic Chemistry, Vol. 42, 3960 [1977]. The reaction of the thiolate with the ester of
- 12 No.371668
Formula (I) is best carried out in a neutral solvent such as toluene or xylene at reflux for 1 to 3 hours. The best results are achieved when the aluminum thiolate compound is in excess of the required stoichiometric amount,
Sulfonamides of formula (IIb) are also prepared from carboxylic acid esters in the thiol esters, as in <sup>5</sup> Equation 8A, according to the method of RP Hatch and SW Weinreb, described in Equation 8, where R, R<sub>2</sub> and R, as defined earlier.
Equation 6A
<img file="AT371668B_D0022.tif" />
toluene
RS-Al-CH
The conditions described for equation 8 are suitable for the conversion of the Sulfonami10 de the formula (IIb) according to equation 8A.
The products of Equation 8A are particularly useful for the preparation of compounds of Formula (Ia) in which Y is a substituent (C0<sub>2</sub>C<sub>i</sub>-C<sub>l)</sub>), in the way described for Equation 3A.
An alternative route for preparing compounds wherein R to Q (Q = O) is attached to a secondary carbon atom involves the reaction of the appropriate dialkylaluminum alcoholate and an ester in which R is a lower primary alkyl group, preferably methyl Equation 9.
Equation 9
<img file="AT371668B_D0023.tif" />
+ (CH <sub>s</sub>) <sub>2</sub> AlO-sec. alkyl
toluene
reflux
<img file="AT371668B_D0024.tif" />
The reaction is carried out in a neutral solvent, such as toluene, which boils at a high enough to bring about the desired reaction at reflux. For best yields, the dialkylaluminum alcoholate is present in greater than the equivalent amount. After refluxing for 1 to 15 hours, the reaction mixture is decomposed with dilute hydrochloric acid solution and the product is extracted with methylene chloride. Evaporation of the methylene chloride gives the desired compound pure enough for the purposes of the invention. The product may be triturated with a solvent, eg, 1-chlorobutane, to remove impurities.
The synthesis of heterocyclic amines has been summarized in The Chemistry of Heterocyclic Compounds, 5 a series published by Interscience Publ., New York and London. 2-Aminopyrimidines are described by DJ Brown in The Pyrimidines, Vcl. XVI of this series described. The 2-amino-1,3,5-triazines are described by KR Huffman and in The Triazines of the same series. The syntheses of triazines are also described by FC Schaefer, U.S. Patent No. 3,154,547 and KR Huffman and FC Schaeffer, J.Org. Chem. 28, 1818 to 1821 [1963].
The preparation of agriculturally suitable salts of the compounds of formula (I), as well as starting and intermediate compounds for these compounds, unless otherwise described herein, are disclosed by the patentee elsewhere.
The new compounds and their preparation are further illustrated in the following specifications, in which temperatures are given in ° C and parts are by weight unless otherwise specified.
Protocol 1: N- [(4,6-dimethylpyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide.
g of 2-amino-4,6-dimethylpyrimidine in 500 ml of anhydrous acetonitrile was added 67 g of 2-methoxycarbonylbenzenesulfonyl isocyanate with stirring at ambient temperature. The resulting mixture was stirred for 16 h and then filtered to remove the desired product which had precipitated as a white solid. Mp 198 to 202 °. It showed infrared absorption peaks at 1750, 1700, 1600 and 1550 cm<sup>l</sup>that corresponded to the desired product.
Protocol 2: N - [(Pyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide.
With stirring at ambient temperature, 1.0 g of 2-aminopyrimidine in 25 ml of anhydrous
Acetonitrile was added to 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate. After stirring this mixture for 24 hours, the formed precipitate was filtered off to give 2.2 g of the desired product melting at 188 to 192 °. It showed infrared absorption peaks at 1700, 1680 and 1580 cm<sup>-1</sup> what the title compound corresponded to.
Protocol 3: N - [(4-Methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide.
A stirred suspension of 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine in 30 ml of anhydrous methylene chloride was admixed at ambient temperature with 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate. After stirring for 16 hours, this mixture was filtered to remove unreacted amine, and the filtrate was evaporated at temperatures up to 40 ° under reduced pressure. The resulting residue was stirred with 25 ml of water, the pg was adjusted to 10 by the addition of 50% sodium hydroxide, and the solution was filtered. Acidification of the filtrate on pg 3 with hydrochloric acid caused the precipitation of the desired product, which, after filtering off and drying, gave 0.8 g of product, mp. 173-179 °. It showed infrared absorption peaks at 1720, 1680, 1630 and 1550 cm<sup>1</sup> what the title compound ent<sup>40</sup> spoke.
Protocol 4: N- [(4,6-Dimethoxypyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide.
A mixture of 1.6 g of 2-amino-4,6-dimethoxypyrimidine, 30 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate was added at ambient temperature and pressure <sup>45</sup> Stirred for 16 h. After filtering off unreacted amine, the filtrate was evaporated at 40 ° C under reduced pressure. The residue thus obtained was stirred with 25 ml of water, the pg value was adjusted to 10 by the addition of 50% sodium hydroxide and the solution was filtered. Acidification of the filtrate on pg 3 caused the formation of a precipitate, which after filtration and drying, 1.7 g of the desired product, mp 185-190 ° he<sup>50</sup> gave. Its infrared absorption peaks at 1700 and 1710 cm<sup>-1</sup> correspond to the desired structure and the NMH absorption peaks at 3.8 and 3.85 correspond to the two different types of
Methoxy groups brought together in this product.
- 14 No.371668
Protocol 5: 2- (Benzyloxycarbonyl) -N- [(4,6-dimethylpyrimidin-2-yl) -aminocarbonyl] -benzenesulfonamide.
1.75 g of 2- (4,6-dimethylpyrimidin-2-yl) aminocarbonylsulfamoyl) benzoic acid were treated with 0.51 g of triethylamine in 10 ml of tetrahydrofuran and 0.88 g of benzyl bromide in 10 ml of tetrahydrofuran 5. The mixture was heated to reflux for 1.5 h, filtered, and the tetrahydrofuran was evaporated in vacuo. The residue was extracted with hot 1-chlorobutane, diluted with ethyl acetate, washed with water and saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered and the solvents were evaporated in vacuo. The resulting residue was crystallized from 1-chlorobutane. This product had a mp of 157 ° and showed absorption peaks in the infrared range of 1720, 1600, 1560 cm<sup>1</sup> in agreement with the desired ester and NMR at 2.65 δ, singlet, for CH<sub>3</sub> ; 5.3s singlet,
CH<sub>2</sub> of benzyl; 6.65 S singlet, CH of pyrimidine and aryl peaks at 7 to 8 δ.
Following the procedures of Regulations 1-4 using an equivalent amount of 2-aminopyrimidines and appropriately substituted sulfonyl isocyanates, the compounds of Table I can be prepared.
Table I
<img file="AT371668B_D0025.tif" />
<img file="AT371668B_D0026.tif" />
Nr.371668
Table I (continued)
<td>QR</td><td>r<sub>2</sub></td><td>H<sub>3</sub></td><td>"5</td><td>X</td><td>Y</td><td>Mp ° C</td>
<td>oic<sub>3</sub>H<sub>7</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>OCH<sub>3</sub></td><td>189-190</td>
<td>0-nC ^ Hg</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>CH 3</td><td>124-126</td>
<td>CnC, H<sub>9</sub></td><td>H</td><td>H</td><td>H</td><td>OCH,</td><td>och<sub>3</sub></td><td>140 - 149</td>
<td>"Ms.</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>OCH 3</td><td>149 - 153</td>
<td>O CHCH..C1<sup>CH</sup>3</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>100-104</td>
<td>OCH <sub>3</sub></td><td>4-Cl</td><td>5-C1</td><td>H</td><td>och<sub>3</sub></td><td>CH 3</td><td>193-194</td>
<td>och<sub>3</sub></td><td>4-Cl</td><td>5-C1</td><td>H</td><td>OCH <sub>3</sub></td><td>och<sub>3</sub></td><td>202-204</td>
<td>och<sub>3</sub></td><td>4-F</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>CH,</td><td>201-203</td>
<td>o-ch<sub>2</sub>CH (C<sub>3</sub>)<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>CH<sub>3</sub></td><td>108-111</td>
<td>o-ch<sub>2</sub>CH (C<sub>3</sub>)<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>OCH <sub>3</sub></td><td>166-168</td>
<td>O (CH<sub>2</sub>) Ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>CH <sub>3</sub></td><td>87-89</td>
<td>OC<sub>2</sub>ch<sub>2</sub>ch<sub>3</sub>1</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>130 - 132</td>
<td>ch<sub>3</sub></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>OCHCH.CH, 1</td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>OCH 3</td><td>153 155</td>
<td>ch<sub>2</sub>ch<sub>3</sub>/</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td><sup>λ</sup>--0</td><td>H</td><td>H</td><td>H</td><td>och <sub>3</sub></td><td>ch<sub>3</sub></td><td>105 - 110</td>
<td>och<sub>2</sub>ch<sub>2</sub>och<sub>2</sub>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>OCHj</td><td>ch<sub>3</sub></td><td>130-134</td>
<td>och<sub>2</sub>ch<sub>2</sub>och<sub>2</sub>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>OCH <sub>3</sub></td><td>OCH 3</td><td>163-166</td>
<td>OiC<sub>8th</sub>H<sub>7</sub></td><td>H</td><td>H</td><td>H</td><td>CH <sub>3</sub></td><td>CH 3</td><td>194-196</td>
<td>OCH <sub>3</sub></td><td>4-F</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>0CH<sub>3</sub></td><td>200 - 202</td>
<td>och<sub>2</sub>ch<sub>2</sub>CH (C<sub>3</sub>)<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>CH 3</td><td>121-124</td>
<td>och<sub>2</sub>ch<sub>2</sub>CH (C<sub>3</sub>)<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>OCHj</td><td>151 - 153</td>
<td>och<sub>2</sub>ch<sub>2</sub>CH (C<sub>3</sub>)<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td>90 - 93</td>
<td>och<sub>2</sub>ch<sub>2</sub>och<sub>2</sub>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>Cl</td><td>Cl</td><td>122-126</td>
<td>o-iC<sub>3</sub>H<sub>7</sub></td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub></td><td>oil</td>
<td>och<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>och<sub>2</sub>cf<sub>3</sub></td><td>156 - 160</td>
<td>och<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>CH<sub>3</sub></td><td>OCHCO.CH, 1 ch<sub>3</sub></td><td>143 - 155</td>
<td>och<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>och<sub>2</sub>co<sub>2</sub>ch<sub>3</sub></td><td>174 - 180</td>
<td>och<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>ch<sub>2</sub>och<sub>3</sub></td><td>154 - 156</td>
<td>OCH,</td><td>K</td><td>H</td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td>159-174</td>
<td>och<sub>2</sub>(ch<sub>2</sub>)<sub>3</sub>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>CH 3</td><td>Cl</td><td>61 - 64</td>
<td>och<sub>2</sub>(ch<sub>2</sub>)<sub>3</sub>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>CH<sub>3</sub></td><td>CH<sub>2</sub>OCH<sub>3</sub></td><td>Oil n "1.5408</td>
<td>och<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>CH 3</td><td>och<sub>2</sub>ch<sub>2</sub>och<sub>3</sub></td><td>118 - 120</td>
- 16 No.371668
Table I (continued)
<td>QR</td><td><sup>R</sup>z</td><td><sup>R</sup>a</td><td><sup>R</sup>s</td><td>X</td><td>Y</td><td>Mp ° C</td>
<td>O (CH<sub>2</sub>) Ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>OCH,</td><td>132-134</td>
<td>O (CH<sub>2</sub>)<sub>5</sub>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>134 - 136</td>
<td>OCH <sub>3</sub></td><td>H</td><td>H</td><td>H</td><td><sup>CR</sup>3</td><td><sup>N</sup>3</td><td>173-176</td>
<td>O (CH<sub>a</sub>CH<sub>a</sub>O)<sub>z</sub>C<sub>z</sub>H ^ Cl</td><td>H</td><td>H</td><td>H</td><td><sup>CR</sup>3</td><td>och<sub>3</sub></td><td>n "1.5458</td>
<td>OCH<sub>Z</sub>CH<sub>Z</sub>OC<sub>Z</sub>H "C1</td><td>H</td><td>H</td><td>H</td><td><sup>CH</sup>3</td><td>OCHj</td><td>124-127</td>
<td>O (CH<sub>2</sub>CH<sub>2</sub>O)<sub>2</sub>C<sub>2</sub>H, C1</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>n '<sup>5</sup> 1.5421</td>
<td>och<sub>2</sub>ch = ch<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>129 - 131</td>
<td>och<sub>2</sub>ch = ch<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>142-145</td>
<td>och<sub>2</sub>ch<sub>2</sub>O-</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>114-117</td>
<td>och<sub>2</sub>ch<sub>2</sub>o / q \</td><td>H</td><td>H</td><td>H</td><td>CI</td><td>CI</td><td>65 - 69</td>
<td>H, C</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>\</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>153-156</td>
<td>\ _ /</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>och<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>2</sub>ch<sub>2</sub>och<sub>3</sub></td><td>och<sub>2</sub>ch<sub>2</sub>och<sub>3</sub></td><td>150 - 152</td>
Alternatively, compounds of Table I wherein R is a group which forms an organic halide with an labile halogen can be prepared according to the procedure of Procedure 5 using equivalent amounts of appropriately substituted benzoic acid derivatives and organohalogens.
Prescription 6: N - [(4,6-Dimethoxy-1, 3,5-triazin-2-yl) -aminocarbonyl] -2- (2-chloroethoxycarbonyl) -benzenesulfonamide.
0.7 g of 2-amino-4,6-dimethoxy-l, 3,5-triazine dissolved in 10 ml of anhydrous methylene chloride, were mixed with 1.45 g of 2- (ß-chloroethoxycarbonyl) benzene sulfonyl isocyanate. After stirring at ambient temperature for 16 hours, the solvent was removed under reduced pressure, the residue triturated with ether and the solid product filtered off: Yield 1.21 g, m.p. 171-174 °. The solid showed infrared absorption peaks at 1705 and 1715 cm<sup>-l</sup> that corresponded to the title product.
Protocol 7: N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2- (2-chloroethoxy-15-pyryl) -benzenesulfonamide.
0.7 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine dissolved in 10 ml of anhydrous methylene chloride were combined with 1.45 g of 2- (β-chloroethoxycarbonyl) -benzenesulfonyl isocyanate with stirring at ambient temperature added. Thereafter, the mixture was stirred for 16 hours. The solvent was evaporated under reduced pressure and the residue was triturated with hexane and filtered to give 1.72 g of the compound, mp 167-170 °. The solid showed infrared absorption peaks at 1700 and 1705 cm<sup>-1</sup>which corresponded to the title compound.
Prescription 8: N - [(4,6-dimethoxy-l, 3,5-triazin-2-yl) -aminocarbonyl] -2- (isopropoxycarbonyl) -benzenesulfonamide.
0.7 g of 2-amino-4,6-dimethoxy-1,3,5-triazine suspended in 5.0 ml of anhydrous methylene chloride was added 1.6 g of 2-isopropoxycarbonylbenzenesulfonyl isocyanate in 5.0 ml of anhydrous methylene chloride. The resulting mixture was filtered to give some unreacted 2-amino17 No. 37668
-4,6-dimethoxytriazine, the filtrate was evaporated under reduced pressure and the residue was triturated with chlorobutane, with 0.5 g of the desired product of mp.
192 were obtained to 195 °. The solid showed infrared absorption peaks at 1705 and
1715 cm <sup>1</sup>which corresponded to the title compound.
Protocol 9: N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl3-2- (isopropoxycarbonyl) -benzenesulfonamide.
26.8 g of 2-amino-4-methoxy-6-methyl-l, 3,5-triazine in 300 ml of anhydrous methylene chloride were mixed with 67.0 g of 2-Isopropoxycarbonylbenzolsulfonyl-isocyanate in 100 ml of anhydrous methylene chloride. The resulting suspension was stirred at ambient temperature for 72 h and then filtered to give 40.0 g of the desired product as a white solid, mp 193-196 °. The solid showed infrared absorption peaks hot 1700 and 1710 cm<sup>-1</sup> which corresponded to the title compound.
Protocol 10: N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide.
A mixture of 1.6 g of 2-amino-4,6-dimethoxy-l, 3,5-triazine, 25 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate was stirred at ambient temperature for 16 h. It was then filtered to remove unreacted amine, and the filtrate was evaporated at 40 ° C under reduced pressure. The residue was triturated with butyl chloride and filtered to give the desired compound which melted over 170 ° with decomposition.
Protocol 11: N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonylfenzenesulfonamide.
An anhydrous suspension of 1.4 g of 2-amino-4-methoxy-6-methyl-l, 3,5-triazine in 25 ml of methylene chloride was added with stirring at ambient temperature and pressure with 2.4 g of 2-Methoxycarbonylbenzolsulfonylisocyanat. The mixture was stirred for 16 h and filtered. The filtrate was evaporated to dryness, the residue triturated with butyl chloride and the product filtered off. The product thus obtained melted at 165 ° and showed absorption peaks in the infrared at 1550, 1600, 1680 and 1700 cm<sup>-1</sup> and in the NMR spectrum at 2.5, 3.65, 4.0 with an aromatic multiplet at 7.2 to 8 ppm.
Following the procedures of Regulations 6 to 11 using equivalent amounts of the corresponding 2-amino-l, 3,5-triazines and correspondingly substituted sulfonyl isocyanates, the compounds of Table II can be prepared.
Protocol 12: N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2- (1-methylpentyloxycarbonyl) -benzenesulfonamide.
2-Hexanol (0.61 g) in 2 ml of dry toluene was added slowly under nitrogen at room temperature to a solution of 1.5 ml (2M) of trimethylaluminum diluted with 5.0 ml of dry toluene. The mixture was stirred at room temperature for 15 minutes and then treated with 0.95 g of N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonylfenzenesulfonamide. The mixture was heated at reflux for 2.5 h under nitrogen, cooled to room temperature and quenched carefully with 20 mL of 10% hydrochloric acid. The organic phase was taken up in methylene chloride, separated, washed with water, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to give 0.65 g of the desired compound, melting at 125-130 °. The infrared spectrum showed characteristic absorption for the product at 3300, 1725, 1730, 1585, 1555 cm
Alternatively, compounds of Tables I and II in which the desired ester group R is a higher alkane (0<sub>5</sub>-0<sub>12</sub> ) is also prepared according to the procedure of Regulation 12 with an equivalent amount of the corresponding aluminum alcoholate and a correspondingly substituted lower alkyl ester.
Nr.371668
Table II
<img file="AT371668B_D0027.tif" />
<td>QR</td><td>r<sub>z</sub></td><td>"3</td><td>Rs</td><td>X</td><td>Y</td><td>Mp ° C</td>
<td>och.</td><td>Η</td><td>Η</td><td>Η</td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td>187 - 189</td>
<td>'- \ J</td><td>Η</td><td>Η</td><td>Η</td><td>ch,</td><td>och.</td><td>160 - 162</td>
<td>och<sub>2</sub>CH (CH,)<sub>2</sub></td><td>Η</td><td>Η</td><td>Η</td><td>ch<sub>3</sub></td><td>och.</td><td>167 - 170</td>
<td>O (CH<sub>2</sub>)<sub>s</sub>ch.</td><td>Η</td><td>Η</td><td>Η</td><td>och.</td><td>och.</td><td>133 - 135</td>
<td>0 - C<sub>3</sub>H<sub>7</sub></td><td>Η</td><td>Η</td><td>Η</td><td>OCH <sub>3</sub></td><td>CH,</td><td>160 - 165</td>
<td>OnC<sub>3</sub>H<sub>7</sub></td><td>Η</td><td>Η</td><td>Η</td><td>OCH,</td><td>OCH</td><td>177 - 179</td>
<td>OnC, H<sub>9</sub></td><td>Η</td><td>Η</td><td>Η</td><td>OCH <sub>3</sub></td><td>OCH</td><td>147 - 150</td>
<td>OnC "H<sub>9</sub></td><td>Η</td><td>Η</td><td>Η</td><td>OCH <sub>3</sub></td><td>CH</td><td>144 - 145</td>
<td>oc<sub>2</sub>H<sub>s</sub></td><td>Η</td><td>Η</td><td>Η</td><td>OCH,</td><td>OCH</td><td>163 - 165</td>
<td>oc<sub>2</sub>H<sub>5</sub></td><td>Η</td><td>Η</td><td>Η</td><td>och,</td><td>CH</td><td>164 - 167</td>
<td>och<sub>2</sub>ch<sub>2</sub>och<sub>2</sub>ch<sub>2</sub>ci</td><td>Η</td><td>Η</td><td>Η</td><td>och,</td><td>CH,</td><td>143 - 144</td>
<td>OCH<sub>2</sub>CH<sub>2</sub>C1</td><td>Η</td><td>Η</td><td>Η</td><td>OCH <sub>3</sub></td><td>OCH</td><td>171 - 174</td>
<td>O (CH<sub>2</sub>)<sub>9</sub>ch.</td><td>Η</td><td>Η</td><td>Η</td><td>OCH <sub>3</sub></td><td>CH</td><td>129 - 130</td>
<td>O (CH<sub>2</sub>)<sub>9</sub>ch,</td><td>Η</td><td>Η</td><td>Η</td><td>OCH <sub>3</sub></td><td>OCH</td><td>94 - 97</td>
<td>/ \</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>6 \</td><td>Η</td><td>Η</td><td>Η</td><td>OCH,</td><td>OCH</td><td>139 - 143</td>
<td>\ _ /</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>och.</td><td>4-C1</td><td>Η</td><td>Η</td><td>och.</td><td>OCH,</td><td>142-145</td>
<td>och<sub>2</sub>ch = ch<sub>2</sub></td><td>Η</td><td>Η</td><td>Η</td><td>och<sub>3</sub></td><td>OCH,</td><td>155-158</td>
<td>0-iC, H<sub>7</sub></td><td>Η</td><td>Η</td><td>Η</td><td>ch,</td><td>CH,</td><td>187 - 189</td>
<td>och<sub>2</sub>ch = ch<sub>2</sub></td><td>Η</td><td>Η</td><td>Η</td><td>OCH,</td><td>CH,</td><td>153-155</td>
<td>och<sub>3</sub></td><td>4-C1</td><td>5-C1</td><td>Η</td><td>och,</td><td>OCH,</td><td>172 - 175</td>
<td>OCH <sub>3</sub></td><td>4-F</td><td>Η</td><td>Η</td><td>OCH 3</td><td>OCH,</td><td>192-194</td>
<td>OCH <sub>3</sub></td><td>4-C1</td><td>5-C1</td><td>Η</td><td>OCH,</td><td>CH,</td><td>159-161</td>
<td>och.</td><td>4-F</td><td>Η</td><td>Η</td><td>OCH,</td><td>CH,</td><td>169 - 172</td>
<td>OC<sub>2</sub>ch<sub>2</sub>ch<sub>3</sub></td><td>Η</td><td>Η</td><td>Η</td><td>0CH<sub>3</sub></td><td>CH,</td><td>136-138</td>
<td>1 ch<sub>3</sub></td><td></td><td></td><td></td><td></td><td>1</td><td></td>
<td>OCH (CH<sub>2</sub>ch)<sub>2</sub></td><td>Η</td><td>Η</td><td>Η</td><td>ch<sub>3</sub></td><td>OCH,</td><td>120 - 123</td>
Nr.371668
Table II (continued)
<td>QR</td><td>& 2</td><td>r<sub>3</sub></td><td>r<sub>5</sub></td><td>X</td><td>Y</td><td>Mp ° C</td>
<td><sup>0CH</sup>z- \ O /<sup>C1</sup></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>192-194</td>
<td>O-CHCH, C1 I <sup>2</sup></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>179 - 181</td>
<td>1 ch<sub>3</sub></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>OCH (CH<sub>2</sub>)<sub>3</sub>ch<sub>3</sub>1</td><td>H</td><td>H</td><td>H</td><td>OCH <sub>3</sub></td><td>ch<sub>3</sub></td><td>125 - 130</td>
<td>ch<sub>3</sub></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>O (CH<sub>2</sub>\ ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>122-125</td>
<td>och<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>N (CH<sub>3</sub>)<sub>2</sub></td><td>190-191</td>
<td>0- \ S y (c.)</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>170 - 172</td>
<td>O-CH-C (CH<sub>3</sub>)<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>120-126</td>
<td>ch<sub>3</sub></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>o-CNCH<sub>2</sub>ch<sub>2</sub>ch = ch<sub>2</sub>!</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td><sup>CH</sup>3</td><td>120-124</td>
<td>ch<sub>3</sub></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>-O \ /</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>132-136</td>
<td>z<sup>ctf</sup>3</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>OCHCHCH, 1</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>144 - 146</td>
<td>1<sup>ε</sup>"<sub>3</sub></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>och<sub>2</sub>ch<sub>2</sub>och<sub>2</sub>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>123 - 127</td>
<td>OCH<sub>2</sub>CH<sub>2</sub>0CH<sub>2</sub>CH<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>168 - 170</td>
<td>och<sub>2</sub>ch<sub>2</sub>och<sub>2</sub>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td></td>
<td>och<sub>2</sub>ch<sub>2</sub>CH (C<sub>3</sub>)<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>137-139</td>
<td>och<sub>2</sub>ch<sub>2</sub>CH (C<sub>3</sub>)<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>125 - 128</td>
<td></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td><sup>CH</sup>3</td><td>125 - 130</td>
<td>0 CCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>130-134</td>
<td>CH (CH<sub>3</sub>)<sub>2</sub>O (CH<sub>2</sub>ch<sub>2</sub>O)<sub>2</sub>c<sub>2</sub>h ^ ci</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>n "-1.5311</td>
<td>och<sub>2</sub>ch<sub>2</sub>O-</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>80 - 84</td>
<td>ψ-θ Ζ ^)<sup>CH</sup>3</td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>och<sub>3</sub></td><td>155-158</td>
- 20 No.371668
Table II (continued)
<td>QR</td><td></td><td><sup>R</sup>3</td><td><sup>R</sup>s</td><td>X</td><td>Y</td><td>Fp. »C</td>
<td>Oi-CJH,</td><td>H</td><td>H</td><td>H</td><td>CH,</td><td>-N (CH,)<sub>a</sub></td><td>151-157</td>
<td>OCH,</td><td>H</td><td>H</td><td>H</td><td>-OCH<sub>2</sub>CH<sub>2</sub>OCH,</td><td>-OCHjCHjOCH,</td><td>142-145</td>
<td>OCH,</td><td>H</td><td>H</td><td>H</td><td>OCH,</td><td>-CH<sub>2</sub>CH<sub>2</sub>OCH,</td><td>100-105</td>
<td>OCH,</td><td>H</td><td>' H</td><td>H</td><td>CH,</td><td>ch<sub>2</sub>ch<sub>2</sub>och.</td><td>Glass</td>
<td>OCH,</td><td>H</td><td>H</td><td>H</td><td>CH,</td><td>ch<sub>2</sub>ch<sub>2</sub>ch<sub>2</sub>och.</td><td>126 - 128</td>
<td>OCH,</td><td>H</td><td>H</td><td>H</td><td>CH,</td><td>-OCH<sub>2</sub>co<sub>2</sub>ch.</td><td>176 - 178</td>
<td>OCH,</td><td>H</td><td>H</td><td>H</td><td>CH,</td><td>-OCH<sub>2</sub>ch<sub>2</sub>och,</td><td>105 - 110</td>
<td>OCH,</td><td>H</td><td>H</td><td>H</td><td>CH,</td><td>-OCH<sub>2</sub>cf,</td><td>165-168</td>
<td>OCH,</td><td>H</td><td>H</td><td>H</td><td>CH,</td><td>-OCH<sub>2</sub>ch<sub>2</sub>och<sub>2</sub>ch,</td><td>125-135</td>
<td>OCH,</td><td>H</td><td>H</td><td>H</td><td>CH,</td><td>-OCH<sub>2</sub>ch<sub>s</sub></td><td>170 - 172</td>
Protocol 13: N - [(5,6-Dimethyl-1,2,4-triazin-3-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide.
A stirred solution of 1.2 g of 3-amino-5,6-dimethyl-l, 2,4-triazine in 25 ml of anhydrous Ace5 tonitril was treated at ambient temperature with 2.4 g of 2-Methoxycarbonylbenzolsulfonylisocyanat. After stirring at ambient temperature for 24 hours, the precipitate formed was filtered off to give 2.5 g of the desired compound, mp 150-151 °. It showed infrared absorption peaks at 1700, 1680 and 1500 cm<sup>-1</sup> which corresponds to the title connection.
Similarly, the compound corresponding to the above compound is also obtained, but in which QR 0GH is obtained<sub>2</sub>CH<sub>2</sub>CH (CH,), is; Fp. 124 to 127 °.
Protocol 14: N- [(2,6-Dimethylpyrimidin-4-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide.
A suspension of 1.2 g of 4-amino-2,6-dimethylpyrimidine in 30 ml of dry acetonitrile was added with stirring 2.4 g of 2-Methoxycarbonylbenzolsulfonylisocyanat. The mixture was stirred for 15 h at ambient temperature and then allowed to stand for 16 h, after which the precipitated desired product was filtered off and washed with butyl chloride. The yield was 2.4 g, mp 125-127 °. The product showed NMR absorption peaks at 4.0, 2.62 and 2.9, corresponding to the product.
When using a suitable N- [(triazinyl) aminocarbonyl] -2-carbonylbenzenesulfonamide 20 or N- [(pyrimidinyl) aminocarbonyl] -2-carbonylbenzenesulfonamide, the compounds of formula (I) indicated in the formulas below can be prepared. For example, the compound of Regulation 10 can be converted to N- [(4,6-dimethoxy-l, 3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonyl-N-methylbenzenesulfonamide by following the methylation reaction according to Equation 2 is carried out as follows: An equivalent amount of sodium hydride (50% mineral oil dispersion) 25 can be added to a solution of the compound of Method 10 in dimethylformamide under a nitrogen atmosphere. After stopping the evolution of hydrogen can be added an equivalent amount of dimethyl sulfate. The resulting reaction mixture may be stirred for 2 to 10 hours and then poured into a large volume of water to form a precipitate which can be filtered off to give the above product.
Nr.371668
<img file="AT371668B_D0028.tif" />
Ο
Protocol 15: N - [(4,6-Dimethylpyrimidin-2-yl) -aminocarbonyl] -2-carboxybenzenesulfonamide A mixture of 2.0 g of N - [(4,6-dimethylpyrimidin-2-yl) -aminocarbonyl] -2 -methoxycarbonylbenzenesulfonamide and 11 ml of 50% aqueous sodium hydroxide were heated with shaking on steam bath 5; 40 ml of water were added and heating and shaking were continued for a further 1/2 hour. The resulting solution was filtered and the filtrate was washed with hydrochloric acid
Acidified PH 2, after which the precipitate formed was filtered off. This gave 0.7 g of the title compound, mp 160 ° (dec.). The NMR spectrum showed resonance peaks for the methyl substituent on the pyrimidine ring at 2.66 ppm and the ring hydrogens at 7.2 to 8.4 ppm. The disappearance of the resonance peak at 4.0 confirmed the conversion of the methyl ester into the carhoxyl group.
Protocol 16: N- [4,6-dimethylpyrimidin-2-yl) -aminocarbonyl] -2-dimethylaminocarbonylbenzenesulfonamide.
4.1 g of N- (4,6-dimethylpyrimidin-2-yl) -2-methoxycarbonylbenzenesulfonamide in 75 ml of toluene were added with 37 ml of a methylene chloride-toluene solution (3: 5) containing 1.25 g of dimethylaluminum dimethyl15-amide with stirring offset at ambient temperature. The mixture was heated to reflux (82 °) for 2 hours, cooled and treated with 10 ml of methanol. After evaporation of the solvents in vacuo, the residue was treated with a mixture of methanol, water, dilute hydrochloric acid, and the precipitated product was filtered off to give 1.25 g of the desired product. Extraction of the aqueous filtrate with methylene chloride provided a further 1.12 g of product, mp 166-168 °. The product showed NMR adsorption peaks of 2.5 ppm, pyrimidine methyl; 2.85 and 3.1 ppm, non-equivalent methyl groups of the dimethylamide;
6.8 ppm, pyrimidine-H; and 7.2 to 8.4 ppm, aromatic hydrogens.
Protocol 17: N - [(4,6-Dimethoxypyrimidin-2-yl) -aminocarbonyl] -2-isopropylaminocarbonylbenzenesulfonamide.
<sup>25</sup> 4.5 g of N- [(4,6-dimethoxypyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide in ml of methylene chloride were added with stirring at ambient temperature to 37 ml of methylene chloride solution containing 1.44 g of dimethylaluminum isopropylamide. The mixture was heated to reflux and the methylene chloride was removed while dry toluene was added until a temperature of 100 ° was reached. Reflux was carried out for 2 h<sup>30</sup> continued at 100 °, after which the mixture was cooled and treated with 10 ml of methanol. To
Evaporation of the solvent in vacuo, the residue was mixed with a mixture of methanol,
Water and dilute HCl and from this aqueous slurry the product was extracted with methylene chloride. Evaporation of the methylene chloride extract gave the product as a solid (4.28 g). Trituration of the product with 1-chlorobutane gave 2.0 g of pure protein
No. 37668, m.p. 148 to 150 ° C, which showed a single spot on TLC. (Silica gel, acetone / hexane 1: 1,
R<sub>f</sub> = 0.34) and in the NMR spectrum gave absorption peaks at 1.15, 4.0, 3.8 to 4.3 and 7.5 to 8.2.
Following the procedure of Regulations 16 and 17 using equivalent amounts of correspondingly substituted dialkylaluminum N-alkylamides and correspondingly substituted esters of
Formula (I), the compounds of Table IIIa and IIIb can be prepared.
Table purple
<img file="AT371668B_D0029.tif" />
R<sub>6</sub>
<td>R</td><td>r<sub>2</sub></td><td>re</td><td>r<sub>5</sub></td><td>re</td><td>X</td><td>Y</td><td>Mp.</td><td>° C</td>
<td></td><td></td><td></td><td></td><td></td><td></td><td></td><td colspan="2"></td>
<td>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>0CH<sub>3</sub></td><td>CH 3</td><td>184 -</td><td>185</td>
<td>CH <sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>OCH <sub>3</sub></td><td>Ί68 -</td><td>170</td>
<td>CH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub>·</td><td>95 -</td><td>102</td>
<td>CH <sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td>166 -</td><td>168</td>
<td>1-c<sub>3</sub>H<sub>7</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>148 -</td><td>150</td>
<td>(CH<sub>2</sub>)<sub>U</sub> CH<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>ch<sub>3</sub>O</td><td>65 -</td><td>70</td>
<td>iC<sub>3</sub>H<sub>7</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>157 -</td><td>158</td>
<td>ch<sub>2</sub>ch = ch<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>148 -</td><td>150</td>
<td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>_ / \ \ _ /</td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>127 -</td><td>130</td>
<td>ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>H</td><td>och<sub>3</sub></td><td>162 -</td><td>165</td>
<td>iC<sub>3</sub>H,</td><td>H</td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td>179</td><td></td>
<td>CH<sub>2</sub></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>/</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>ch;</td><td>H</td><td>H</td><td>H</td><td>H</td><td>CH,</td><td>OCH,</td><td>122 -</td><td>124</td>
<td>\</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>ch<sub>2</sub></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>- (CHJ, - *</td><td>H</td><td>H</td><td>H</td><td>*</td><td>ch<sub>3</sub></td><td>och<sub>3</sub></td><td>175 -</td><td>177</td>
<td>- (CH<sub>2</sub>) - *</td><td>H</td><td>H</td><td>H</td><td>*</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>189 -</td><td>191</td>
<td>- (ch<sub>2</sub>) "- *</td><td>H</td><td>H</td><td>H</td><td>*</td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td>180 -</td><td>181</td>
<td>- (ch<sub>2</sub>)<sub>2</sub>O (CH<sub>2</sub>)<sub>2</sub>- *</td><td>H</td><td>H</td><td>H</td><td>*</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>162 -</td><td>164</td>
<td>ch<sub>2</sub>c<sub>6</sub>H<sub>5</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>112 -</td><td>117</td>
<td>ch<sub>2</sub>c<sub>G</sub>H<sub>5</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>ch<sub>3</sub></td><td>75 -</td><td>85</td>
* R and R<sub>6</sub> are zusannengenomnen.
- 23 Nr.371668
Table Illb
<img file="AT371668B_D0030.tif" />
R<sub>e</sub>
<td>R</td><td>H<sub>2</sub></td><td></td><td>H<sub>S</sub></td><td>r<sub>6</sub></td><td>X</td><td>Y</td><td>Mp ° C</td>
<td>CH <sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>0CH<sub>3</sub></td><td>och<sub>3</sub></td><td>166-168</td>
<td>CH <sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>och<sub>3</sub></td><td>172</td>
<td>(ch<sub>2</sub>)<sub>u</sub> ch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>107-109</td>
<td>(0 /</td><td>H</td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub>O</td><td>ch<sub>3</sub>O</td><td>217-220</td>
<td>iC<sub>3</sub>H, / \</td><td>H</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>och<sub>3</sub></td><td>102</td>
<td>_ / \ \ __ /</td><td>D</td><td>H</td><td>H</td><td>H</td><td>ch<sub>3</sub></td><td>och<sub>3</sub></td><td>127 - 130</td>
<td>ch<sub>2</sub>ch = ch<sub>2</sub></td><td>H</td><td>H</td><td>H</td><td>H</td><td><sup>ch</sup>3</td><td>och<sub>3</sub></td><td>118 - 120</td>
Protocol 18: N - [(4-Methoxy-6-methyltriazin-2-yl) -aminocarbonyl] -2- {methylthio) carbonylhenzenesulfonamide.
Trimethylaluminum (6.0 mL, 2M) was injected under nitrogen atmosphere into 15 mL of dry toluene 5 to give 3.8 g of N - [(4-methoxy-6-methyltriazin-2-yl) -aminocarbonyl] -2-methoxycarbonyl-benzenesulfonamide added in portions. After stirring at room temperature for 1 hour, methyl mercaptan (gas) was passed through the reaction mixture until the initial temperature increase ceased, after which the addition was stopped. The reaction mixture was stirred at room temperature for 1 h and then quenched with 25 mL of 10% HCl. The resulting white suspension 10 was filtered off to give 2.9 g of white solid, the infrared absorption peaks at 1740 and
1690 cm<sup>-1</sup> showed, according to the title compound.
Protocol 19: N- [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-n-butylthio) -carbonybenzenesulfonamide.
Trimethylaluminum (1.5 ml, 2M) was injected under nitrogen atmosphere into 0.5 ml of dry toluene 15 and 0.54 g (0.006 mol) of n-butanethiol in 2.0 ml of toluene was added dropwise. Then N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide (0.95 g) was added portionwise and the mixture was allowed to stand for 3 h Heated to 80 °. After cooling to room temperature, the mixture was quenched with 25 ml of 10% HCl. Methylene chloride was added, separated, dried over magnesium sulfate, filtered and evaporated to give a crude oil. Trituration with hexanes gave 0.6 g of white solid, mp 115-120 °, the infrared absorption peaks at 1725, 1680, 1600 and 1560 cm<sup>1</sup> showed, according to the title compound.
Protocol 20: N - [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-isopropylthiocarbonylbenzenesulfonamide.
1.5 ml (2N) of trimethylaluminum in 5 ml of dry toluene were added dropwise under nitrogen
- 24 Nr.371668 with 0.48 g (6.0 mmol) of 2-propanethiol in 2 ml of toluene. The resulting aluminum reagent was stirred for 15 min at room temperature, after which 0.95 g (2.5 mmol) of N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] - 2-methoxycarbonylbenzenesulfonamide were added all at once. The
Suspension was heated at 80 ° for 3 h, cooled to room temperature and treated with 10% HCl (15 ml). The mixture was stirred until a fine solid precipitated, which was filtered off, washed with hexanes and air dried to give 0.4 g of product, mp 155-158 °. It showed infrared absorption peaks corresponding to the title compound.
Following the procedure of Regulations 18 to 20 using equivalent amounts of a suitably substituted dialkyl aluminum alkyl thiolate and suitably substituted esters of formula (I), the compounds of Table IVa can be prepared.
<img file="AT371668B_D0031.tif" />
Nr.371668
Table IVb
<img file="AT371668B_D0032.tif" />
II o
<td>QR</td><td></td><td>R</td><td><sup>R</sup>s</td><td>X</td><td>Y</td><td>Mp ° C</td>
<td>sch<sub>3</sub></td><td>H</td><td>H</td><td>H</td><td>CH<sub>S</sub></td><td>OCH,</td><td>144 - 146</td>
<td>Sn (C ^ H<sub>G</sub>)</td><td>H</td><td>H</td><td>H</td><td>OCHj</td><td>ch<sub>3</sub></td><td>115 - 120</td>
<td>-SCHCH, 1</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>177 - 178</td>
<td>ch<sub>3</sub></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>-<sup>ski</sup>-\O/</td><td>H</td><td>H</td><td>H</td><td>och<sub>3</sub></td><td>ch<sub>3</sub></td><td>125 - 130</td>
preparations
Useful preparations of the compounds of the formula (I) can be prepared by conventional methods. They include dusts, granules, pellets, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of them can be applied directly. Sprayable preparations can be stretched with suitable media and used in spray volumes of several liters to several hundred liters / ha. In general, the formulations contain about 0.1 to 99% by weight active ingredient (s) and at least a) about 0.1 to 20% surfactant (s) and b) about 1 to 99.9% solids (s) or liquid (s) diluent. More specifically, these ingredients may be present in the approximate proportions shown in Table X.
- 26 No.371668
Table X
<td rowspan="2"></td><td colspan="3">Wt .-% <sup>+</sup>)</td>
<td>active component</td><td>thinner</td><td>wetting agent</td>
<td>wettable powder oil suspensions emulsions including emulgierharer concentrates aqueous suspensions dusts Granules and pellets</td><td>20 - 90 3 - 50 10 - 50 1 - 25 0.1-95</td><td>0-74 40 - 95 40 - 84 70 - 99 5 - 99.9</td><td>1-10 0-15 1-20 0 - 5 0-15</td>
+)
Active ingredient plus at least one wetting agent or thinner equal to 100% by weight.
Of course, lower or higher levels of active ingredient may be present, depending on the intended use and the physical properties of the compound. Sometimes higher ratios of wetting agent to active ingredient are desired, and they are achieved by adding to the formulation or by mixing in the tank.
Typical solid diluents are described in Watkins et al. Handbook of Insecticide Dust Diluents and Carriers, 2nd ed. Dorland Books, Daldwell, New Jersey. The more absorbent diluents are preferred for wettable powders and the denser for dusts. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd ed., Inter10 science, New York, 1950. A solubility below 0.1% is preferred for suspension concentrates; Solution concentrates are preferably stable at 0 ° C against phase separation. Coputcheon's Detergents and Emulsifiers Annual MC Publishing Corp. of Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publishing Co., Inc., New York, 1964, have compiled surfactants and their recommended uses. 15 All preparations may contain small amounts of additives to reduce the foaming, the
Caking containing corrosion, microbiological growth, etc.
Methods for preparing such preparations are well known. Solutions are obtained by simply mixing the ingredients. Fine solid preparations are prepared by mixing and - usually - grinding eg in a hammer mill. Suspensions are<sup>20</sup> by wet milling (see, for example, US Pat. No. 3,060,084). Granules and pellets can be prepared by spraying the active material on preformed granular carriers or by agglomeration processes. See JE Browning, Agglomeration, Chemical Engineering, Dec. 4, 1967, pp. 147ff. and Perry's Chemical Engineer's Handbook, 4th ed., McGraw-Hill, New York,
1963, pp. 8 to 59ff.
<sup>25</sup> Further information on the preparation of preparations can be found, for example, in the following references:
U.S. Patent No. 3,235,361, column 6, line 16 to column 7, line 19 and examples 10 to 41;
US Pat. No. 3,309,192, column 5, Z. 43 to column 7, Z. 62 and examples 8, 12, 15, 39, 41, 52,
53, 58, 132, 138-140, 162-164, 166, 167, 169-182.
- 27 No.371668
U.S. Patent No. 2,891,855, Col. 3, Z. 66 to Col. 5, Z. 17 and Examples 1 to 4.
GC Klingman, Weed Control as a Science, John Wiley & Sons, Inc., New York, 1961, pp. 81 to 96.
JD Fryer and SA Evans, Weed Control Handhook, 5th Ed., Blackwell Scientific Publications, Oxford 1968, pp. 43-44. 101 to 103.
Example 1: wettable powders
N- [(4,6-dimethoxypyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 95%
Dioctyl sodium sulfosuccinate 0.1%
Sodium lignosulfonate 1% synthetic fine SiO<sub>2</sub> 4%
The ingredients are mixed and ground in a hammer mill to particles almost all of which are less than 100 microns in size. This material is sieved through a sieve with 0.3 mm openings and packaged.
Example 2: Grains
Wettable Powder of Example 23 10%
Attapulgite grains 90% (0.84 - 0.42 mm)
A slurry of 50% solids wettable powder is sprayed onto the surface of attapulgite grains in a twin-cone mixer. The grains are dried and packaged.
Example 3: wettable powder
N- [(4-methyl-6-methoxy-1,3,5-triazine-25-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 40%
Dioctyl-n-atriumsulfosuccin at 1.5%
Sodium lignosulfonate 3% low-viscosity methylcellulose 1.5%
Attapulgite 54%
The ingredients are thoroughly mixed and passed through an air mill to bring them to an average particle size below 15μ, remixed and sieved through a sieve with 0.3mm openings prior to packaging.
Example 4: Grains
Wettable Powder of Example 2 25%
Plaster 64%
Potassium sulphate 11%
The ingredients are mixed in a rotating mixer and the mixture is sprayed with water to achieve granulation. When most grains reach 1.040 to 0.42 mm in size, they are removed, dried and sieved. Too coarse material is crushed to obtain additional material in the desired range. The grains formed contain 10% active ingredient.
Example 5: Wettable powder
N- [(4,6-dimethoxy-l, 3,5-triazin-2-yl) 45 -aminocarbonyl] -2-methoxycarbonylphenolsulfonamide 65%
Dodecylphenol polyethylene glycol ether
2%
- 28 Nr.371668
sodium ligninsulfonate
N atriumsilico alutnin at
Montmorillonite (calcined)
4%
6%
23%
The ingredients are thoroughly mixed. The liquid wetting agent is added by spraying onto the solid ingredients in a mixer. After milling in a hammer mill to particles almost all smaller than 100 μ, the material is again mixed, sieved through a sieve with openings of 0.3 mm and packaged.
Example 6: Oil suspension
N- [(4-methyl-6-methoxypyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 25%
Polyoxyethylene sorbihexaoleate 5% high aliphatic hydrocarbon oil 70%
The ingredients are mixed in a sand mill until the solid particles are reduced to less than 5μ. The resulting suspension can be used directly, but preferably after further oiling or emulsifying in water.
Example 7: Aqueous suspension
N- [(4,6-dimethyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonyl 1-.
benzenesulfonamide 25% hydrated attapulgite 3% crude calcium lignosulfonate 10%
Sodium dihydrogen phosphate 0.5%
Water 61.5%
The ingredients are ground in a ball or roller mill until the solid particles are reduced to less than 10 microns and then packaged.
Example 8: Extruded pellets
N- [(4,6-dimethylpyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 25% anhydrous sodium sulfate 10% crude calcium lignosulfonate 5%
Sodium alkylnaphthalenesulfonate 1%
Calcium / magnesium bentonite 59%
The ingredients are mixed, ground in the hammer mill and then moistened with about 12% water. The mixture is extruded in the form of cylinders of about 3 mm diameter, which are then cut into pellets of about 3 mm in length. The pellets may be used directly after drying, or the dried pellets may be crushed so that they pass through a sieve with openings of 0.84 mm. The granules, which are retained by a 0.42 mm sieve, are packaged for use and the fines are returned.
Example 9: Solution
N- [(4,6-dimethoxy-l, 3,5-triazin-2-yl) -aminocarbonyl] -2-methoxy carbonyl 1-benzenesulfonamide 5%
dimethylformamide
95%
Nr.371668
The ingredients are combined and stirred to form a solution suitable for
Application of small volumes can be used.
Example 10: Wettable powder
N- [(4,6-dimethylpyrimidin-2-yl) 5 -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 80%
Sodium alkylnaphthalenesulfonate 2%
Sodium lignosulfonate 2% synthetic amorphous SiO<sub>2</sub> 3%
Kaolinite 13%
The ingredients are thoroughly mixed and ground in a hammer mill until substantially all of the particles are smaller than 100 microns: the material is remixed, sieved through a sieve with 0.3 mm orifices and packaged.
usability
The compounds used in the agents according to the invention are highly active herbicides.
The compositions according to the invention are suitable for broadband weed control before and after sprouting wherever complete destruction of all vegetation is desired, such as around fuel tanks, ammunition depots, industrial deposits, oil production facilities, access roads to theaters and the like, along highways and railway facilities , By proper choice of rate and
At the time of application, they can also be used for a favorable modification of plant growth and for the selective control of weeds in crops such as wheat and barley.
The exact amount of Compound (I) to be used in a given case will vary according to the particular end result desired, the amount of leaves present, the weed species to be controlled, the type of crop, the type of soil, the preparation and the mode of application, weather conditions, etc. Since so many variables are involved, it is not possible to give an exact application rate suitable for all situations. In general, the compounds are used in amounts of about 0.005 to 20 kg / ha, preferably in a range of 0.125 to 10 kg / ha. The higher rates of this range are generally used in adverse conditions or when long term soil persistence is desired and lower rates for selective weed control in crops.
Combinations of the agents according to the invention with known herbicides likewise lead to an effective control of weeds by hot small-grain crops such as wheat and barley. 35 Typical herbicides for this purpose are: Chlorotoluron [3- (3-chloro-4-methylphenyl) -l, l-dimethylurea], MCPP [(+) - 2- (4-chloro-2-methylphenoxy) -propanoic acid], metoxuron [3- (3-chloro 4-methoxyphenyl) -1, 1-dimethylurea], methabenzothiazuron [1- (benzothiazol-2-yl) -l, 3-dimethylurea], dichlorofop {methyl 2- [4- (2,4-dichlorophenoxy) -phenoxy ] -propanolate)}, triallate [S-2,3-dichloroallyl-di-isopropylthiocarbamate], isoproturon [3- (4-isopropylphenyl) -l, l-dimethylurea], or difenzo40 quat [l, 2-dimethyl-3,5-diphenylpyrazolium ion].
However, the agents according to the invention can also be combined with other herbicides and are particularly suitable in combination with ureas such as 3- (3,4-dichlorophenyl) -1, 1-dimethylurea, 3- (3,4-dichlorophenyl) -1-methoxy 1-methylurea and 1,1-dimethyl-3- (a, a, a -trifluoro-m-tolyl) -urea; Triazines such as 2-chloro-4- (ethylamino) -6- (isopropylamino) -s-triazine; Uracils such as 5-bromo-345-sec-butyl 1-6-methylur acyl; N- (Phosponomethyl) glycine; 3-cyclohexyl-l-methyl-6-dimethylamino-s-triazine-2,4 (lH, 3H) -dione; N, N-dimethyl-2,2-diphenylacetamide; 2,4-dichlorophenoxyacetic acid and closely related compounds); 4-chloro-2-butynyl-3-chlorophenylcarbamate; Diisopropylthiolcarbamic acid S- (2,3,3-trichloroallyl) ester: ethyl 1-N-henzoyl 1-N- (3,4-dichlorophenyl) -2-aminopropionate: 4-amino-6-tert. buty1-3- (methylthio) -1,2,4-triazine-5 (4H) -one; 3-isopropyl-1H-2,1,3-benzothiodiazine (4) -3H-on-50,2,2-dioxyd; a, α, α-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine; 1, 1'-dimethy 1-4, 4'-bipyridinium ion; Monosodium methanarsonat; and 2-chloro-2 ', 6'-diethyl (methoxymethyl) acetanilide.
- 30 No.371668
The effectiveness of the new compounds was found in a number of greenhouse and field tests. The tests are described below and the results obtained are listed. The ratings are based on a number scale from 0 = no effect to 10 = maximum effect. The associated symbols have the following meanings:
C = chlorosis or necrosis
D = defoliation E = inhibition of sprouting G = growth retardation H = strain effects' ü = unusual pigmentation
6Y = Dropped buds and flowers, Test A
Crabgrass (Digitaria Sp.) Seeds, millet (Echinochloa crusgalli), wild oat (Avena fatua), cassia (Cassia tora), morning glory (Ipomoea sp.), Burdock (Xanthium sp.), Sorghum, 15 corn, soybean, rice, Wheat and cypressgrass (Cyperus rotundus) were planted in a growth medium and treated with the compounds of Table XII dissolved in a non-phytotoxic solvent prior to sprouting. Other seeds and tubers of all of the above weeds and crops were planted for control at the same time. The control plants were untreated, ie neither one of the compounds nor a solvent was used. At the same time cotton with five leaves (including cotyledons), bush beans with the third trefoil in development, finger-millet with two leaves, millet-millet with two leaves, wild-oat with two leaves, cassia with three leaves (including the cotyledons), four-leaf ( including cotyledons), four-leafed burdock (including cotyledons), four-leafed sorghum, three-leafed corn, soybeans with two cotyledons, Rice with three leaves, wheat with one leaf and Cyprus grass with three to five leaves with solutions of the compounds of Table XII sprayed in a non-phytotoxic solvent. Other groups of the same weeds and crops were sprayed with only the same non-phytotoxic solvent and served as control plants. Plants and control plants treated before and after sprouting were kept in a greenhouse for 16 days, 30 after which all treated plants were compared with the corresponding control plants and visually assessed for their response to treatment. The data in Table XII show that the compounds of general formula (I) are very effective herbicides.
Nr.371668
Table XII
<td></td><td>35 0 \</td><td colspan="3">O 101</td><td>n EC n 0 SC 0 0 \ / X / 0</td><td>33 03 Ο O Ο O \/O 101</td>
<td></td><td></td><td></td><td></td><td></td><td>£ 3</td><td>w</td>
<td></td><td></td><td>£ 2</td><td></td><td></td><td>2 1</td><td></td>
<td></td><td></td><td>1</td><td></td><td></td><td>0 = 0</td><td>0 = 0</td>
<td></td><td>c</td><td colspan="2">= 0</td><td></td><td>1</td><td>1</td>
<td></td><td></td><td>1</td><td></td><td></td><td>£ 3</td><td>33</td>
<td></td><td></td><td>£ 2</td><td></td><td></td><td>2 l</td><td>2 1</td>
<td></td><td></td><td>1</td><td>N</td><td>53</td><td>N -J " 0 s</td><td>N « 0 s</td>
<td></td><td></td><td>c</td><td></td><td>0</td><td>M ti</td><td>ω O</td>
<td></td><td></td><td colspan="2">w</td><td></td><td>1 O</td><td>1 0</td>
<td></td><td></td><td>1</td><td></td><td>0-0</td><td>0 = 0</td><td>0 = 0</td>
<td></td><td></td><td>)</td><td></td><td>./</td><td>λ /</td><td>A /</td>
<td></td><td></td><td colspan="2">0</td><td></td><td>IO!</td><td>101</td>
<td></td><td></td><td colspan="2"></td><td>z</td><td></td><td></td>
<td>kg / ha</td><td colspan="2">0.4</td><td colspan="2">2.0</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td></td><td></td><td>9C</td><td>9C</td><td>9C</td>
<td>cotton</td><td>9C</td><td></td><td></td><td>9C</td><td>9C</td><td>9C</td>
<td>Morning Glory</td><td>IOC</td><td></td><td></td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>IOC</td><td></td><td></td><td>9C</td><td>9C</td><td>9C</td>
<td>Kassie</td><td>9C</td><td></td><td></td><td>9C</td><td>9C</td><td>9C</td>
<td>Cyprus grass</td><td>9C</td><td></td><td></td><td>9C</td><td>9C</td><td>IOC</td>
<td>crabgrass</td><td>9C</td><td></td><td></td><td>9C</td><td>5C, 9G</td><td>5C.8G</td>
<td>barnyardgrass</td><td>IOC</td><td></td><td></td><td>IOC</td><td>9C</td><td>9C</td>
<td>Wild oats</td><td>9C</td><td></td><td></td><td>9C</td><td>9C</td><td>9C</td>
<td>wheat</td><td>9C</td><td></td><td></td><td>9C</td><td>9C</td><td>9C</td>
<td>Corn</td><td>9C</td><td></td><td></td><td>9C</td><td>IOC</td><td>9C</td>
<td>soybeans</td><td>9C</td><td></td><td></td><td>6C.9G</td><td>9C</td><td>9C</td>
<td>rice</td><td>IOC</td><td></td><td></td><td>IOC</td><td>5C.9G</td><td>8C</td>
<td>sorghum</td><td>9C</td><td></td><td></td><td>IOC</td><td>9C</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>Morning Glory</td><td>9G</td><td></td><td></td><td>9G</td><td>9G</td><td>9G</td>
<td>barnacles</td><td>9G</td><td></td><td></td><td>9G</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>8G</td><td></td><td></td><td>9G</td><td>9G</td><td>9G</td>
<td>Cyprus grass</td><td>10E</td><td></td><td></td><td>10E</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td>9G</td><td></td><td></td><td>9G</td><td>9H</td><td>9H</td>
<td>barnyardgrass</td><td>9H</td><td></td><td></td><td>9H</td><td>9H</td><td>9H</td>
<td>Wild oats</td><td>3C, 9H</td><td></td><td></td><td>3C, 9H</td><td>9H</td><td>9H</td>
<td>wheat</td><td>9H</td><td></td><td></td><td>9H</td><td>9H</td><td>9H</td>
<td>Corn</td><td>10E</td><td></td><td></td><td>10E</td><td>10H</td><td>9H</td>
<td>soybeans</td><td>9H</td><td></td><td></td><td>9H</td><td>9H</td><td>10E</td>
<td>rice</td><td>10E</td><td></td><td></td><td>10E</td><td>'10E</td><td>10E</td>
<td>sorghum</td><td>10E</td><td></td><td></td><td>10E</td><td>9H</td><td>9H</td>
COCH, <sup>X</sup>OCH
Nr.371668
Table XII (continued)
<td></td><td>x ox O ü \/O 101</td><td>XX OO oo IOI Σ, z</td><td>x "X * O / V O</td>
<td></td><td>X</td><td>X</td><td>X</td>
<td></td><td>2</td><td>?</td><td>2</td>
<td></td><td>1</td><td>0 = 0 l</td><td>= °?</td>
<td></td><td>X</td><td>π</td><td>X</td>
<td></td><td>2</td><td>2</td><td>2</td>
<td></td><td></td><td></td><td></td>
<td></td><td>oa</td><td>O. X</td><td>oa</td>
<td></td><td>Where</td><td>Where</td><td>ra o</td>
<td></td><td>1 °</td><td>1 O</td><td>1 °</td>
<td></td><td>0 = 0</td><td>0 = 0</td><td>0 = 0</td>
<td></td><td></td><td>A /</td><td>A /</td>
<td></td><td>101</td><td>IO</td><td>IOI</td>
<td></td><td>\ z</td><td></td><td></td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>2</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>9C</td><td>5C.10D</td>
<td>cotton</td><td>9C</td><td>5U, 5C, 9G</td><td>5C.9G</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td>5G.9G</td>
<td>barnacles</td><td>9C</td><td>9C</td><td>9C</td>
<td>Kassie</td><td>-</td><td>9C</td><td>9C</td>
<td>Cyprus grass</td><td>9C</td><td>9C</td><td>9C</td>
<td>crabgrass</td><td>IOC</td><td>9C</td><td>9C</td>
<td>barnyardgrass</td><td>IOC</td><td>IOC</td><td>9C</td>
<td>Wild oats</td><td>IOC</td><td>4C.7G</td><td>9G</td>
<td>wheat</td><td>IOC</td><td>3C.7G</td><td>IOC</td>
<td>Corn</td><td>IOC</td><td>IOC</td><td>5U, 9C</td>
<td>soybeans</td><td>9C</td><td>9C</td><td>9C</td>
<td>rice</td><td>IOC</td><td>IOC</td><td>9C</td>
<td>sorghum</td><td>IOC</td><td>9C</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>Morning Glory</td><td>9H</td><td>9G</td><td>9C</td>
<td>barnacles</td><td>9G</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>9G</td><td>9G</td><td>9C</td>
<td>Cyprus grass</td><td>10E</td><td>9G</td><td>10E</td>
<td>crabgrass</td><td>10E</td><td>9H</td><td>4C, 9G</td>
<td>barnyardgrass</td><td>9H</td><td>9H</td><td>9H</td>
<td>Wild oats</td><td>9H</td><td>9G</td><td>9H</td>
<td>wheat</td><td>9H</td><td>9G</td><td>9H</td>
<td>Corn</td><td>10E</td><td>9G</td><td>9G</td>
<td>soybeans</td><td>9H</td><td>9H</td><td>9H</td>
<td>rice</td><td>10E</td><td>10Ξ</td><td>10E</td>
<td>sorghum</td><td>9H</td><td>9G</td><td>9H</td>
- 33 Nr.371668
Table XII (continued)
<td></td><td>© 1 2 2 \ z</td>
<td></td><td>EC 2</td>
<td></td><td>0 = 0</td>
<td></td><td>33 2 1</td>
<td></td><td>o * sc ω o</td>
<td></td><td>| 0 = 8 A / IOI</td>
<td>kg / ha</td><td>2</td>
<td>After sprouting</td><td></td>
<td>bush beans</td><td>6C, 9G</td>
<td>cotton</td><td>3C, 9G</td>
<td>Morning Glory</td><td>5C.8G</td>
<td>barnacles</td><td>5C.9G</td>
<td>Kassie</td><td>3C, 6G</td>
<td>Cyprus grass</td><td>1C, 8G</td>
<td>crabgrass</td><td>5C.8G</td>
<td>barnyardgrass</td><td>9C</td>
<td>Wild oats</td><td>2G</td>
<td>wheat</td><td>5G</td>
<td>Corn</td><td>1C.8G</td>
<td>soybeans</td><td>2C, 8G</td>
<td>rice</td><td>3C.8G</td>
<td>sorghum</td><td>2C.8G</td>
<td>Before sprouting</td><td></td>
<td>Morning Glory</td><td>5C, 9G</td>
<td>barnacles</td><td>9G</td>
<td>Kassie</td><td>9G</td>
<td>Cyprus grass</td><td>10E</td>
<td>crabgrass</td><td>2C, 8G</td>
<td>barnyardgrass</td><td>2C, 9H</td>
<td>Wild oats</td><td>8G</td>
<td>wheat</td><td>8G</td>
<td>Corn</td><td>9G</td>
<td>soybeans</td><td>2C.8H</td>
<td>rice</td><td>10E</td>
<td>sorghum</td><td>9G</td>
- 34 No.371668
Table XII (continued)
<td></td><td colspan="2">IOI v \</td><td>C II A <O> -</td><td colspan="2">IOI</td>
<td></td><td></td><td></td><td>i</td><td></td><td>0 = 0</td>
<td></td><td>1</td><td>0 = 0</td><td>O CM 1</td><td></td><td>1 O</td>
<td></td><td>cf</td><td>O</td><td>Ο «M</td><td>O</td><td>1</td>
<td></td><td>co</td><td>1</td><td>2 p</td><td>CO 1</td><td>e</td>
<td></td><td>52</td><td>53</td><td>53 cm</td><td>53</td><td>O</td>
<td></td><td>£</td><td>O</td><td>ZE</td><td>2</td><td>N</td>
<td></td><td>1 0 = 0</td><td>w 53</td><td>0 = 0 S<sup>5</sup></td><td>J 0 = 0</td><td>53 O</td>
<td></td><td>1 □ 2</td><td>O</td><td>BC 0</td><td>53</td><td>l r-4</td>
<td></td><td>Z</td><td rowspan="2">i-1 O</td><td>2 I</td><td>z</td><td>O</td>
<td></td><td>A</td><td></td><td>A</td><td></td>
<td></td><td>2 2 II 1</td><td></td><td>2 2</td><td>1 II</td><td></td>
<td></td><td>II 1 O, o / A / 53</td><td>\ O</td><td>/ V \.</td><td>1 II OZ<sup>ü</sup>/ ΆΑ</td><td>\</td>
<td></td><td>O</td><td></td><td>O SB</td><td>O</td><td>O</td>
<td></td><td>m</td><td>e</td><td>"O</td><td>rt</td><td></td>
<td></td><td>53</td><td>O</td><td>53</td><td>e</td><td>53</td>
<td></td><td>O</td><td></td><td>0</td><td>O</td><td>Ο</td>
<td>kg / ha</td><td colspan="2">0.4</td><td>0,4 '</td><td colspan="2">0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td></td><td>9C</td><td>9C</td><td></td>
<td>cotton</td><td>9C</td><td></td><td>9C</td><td>9C</td><td></td>
<td>Morning Glory</td><td>IOC</td><td></td><td>IOC</td><td>IOC</td><td></td>
<td>barnacles</td><td>IOC</td><td></td><td>IOC</td><td>IOC</td><td></td>
<td>Kassie</td><td>9C</td><td></td><td>IOC</td><td>IOC</td><td></td>
<td>Cyprus grass</td><td>9C</td><td></td><td>IOC</td><td>IOC</td><td></td>
<td>crabgrass</td><td>2C, 6G</td><td></td><td>3C, 7G</td><td>2C</td><td></td>
<td>barnyardgrass</td><td>IOC</td><td></td><td>IOC</td><td>2C, 9H</td><td></td>
<td>Wild oats</td><td>2C, 6G</td><td></td><td>2C, 8G</td><td>2C, 5G</td><td></td>
<td>wheat</td><td>3C, 6G</td><td></td><td>3C, 7G</td><td>IC</td><td></td>
<td>Corn</td><td>2U, 9G</td><td></td><td>IOC</td><td>3C, 9G</td><td></td>
<td>soybeans</td><td>IOC</td><td></td><td>5C.9G</td><td>3C, 9G</td><td></td>
<td>rice</td><td>3C, 8G</td><td></td><td>3C, 8G</td><td>6G</td><td></td>
<td>sorghum</td><td>IOC</td><td></td><td>9C</td><td>2H, 8G</td><td></td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>Morning Glory</td><td>9G</td><td></td><td>9C</td><td>9C</td><td></td>
<td>barnacles</td><td>9G</td><td></td><td>9G</td><td>9G</td><td></td>
<td>Kassie</td><td>4C, 8G</td><td></td><td>9C</td><td>5C.9G</td><td></td>
<td>Cyprus grass</td><td>10E</td><td></td><td>10E</td><td>10E</td><td></td>
<td>crabgrass</td><td>2C, 5G</td><td></td><td>2C.6G</td><td>4G</td><td></td>
<td>barnyardgrass</td><td>9H</td><td></td><td>10H</td><td>2C.9G</td><td></td>
<td>Wild oats</td><td>9G</td><td></td><td>5C.9H</td><td>8G</td><td></td>
<td>wheat</td><td>9G</td><td></td><td>9H</td><td>5G</td><td></td>
<td>Corn</td><td>2U, 9G</td><td></td><td>10H</td><td>9G</td><td></td>
<td>soybeans</td><td>9H</td><td></td><td>9H</td><td>9H</td><td></td>
<td>rice</td><td>10E</td><td></td><td>10E</td><td>9H</td><td></td>
<td>sorghum</td><td>9H</td><td></td><td>10H</td><td>9G</td><td></td>
- 35 No.371668
Table XII (continued)
<td></td><td></td><td></td><td></td><td></td><td></td>
<td></td><td></td><td>IOI</td><td>IOI</td><td>IOI</td><td></td>
<td></td><td></td><td>/ γ</td><td>ζγ</td><td colspan="2">v \</td>
<td></td><td>O-</td><td>-O</td><td>0 = 0</td><td></td><td>ü - o 1</td>
<td></td><td></td><td>? O</td><td>? O</td><td>OJ O</td><td>O 1</td>
<td></td><td></td><td>03 'p</td><td>33 φ</td><td>VA</td><td>33</td>
<td></td><td></td><td>O SB</td><td></td><td>1 33</td><td>O 1</td>
<td></td><td></td><td>λ?</td><td>F</td><td>2</td><td>w</td>
<td></td><td>/</td><td>\ ° = v</td><td>/ \ <sup>o ==</sup>?</td><td>0 = 0</td><td></td>
<td></td><td rowspan="3">e O</td><td>\ 33</td><td></td><td>ffi</td><td>O</td>
<td></td><td rowspan="2">Y 2 2 1 II</td><td rowspan="2">33 33 Z ° ο ώ ZY</td><td>z</td><td></td>
<td></td><td>Z% ll</td><td></td>
<td></td><td></td><td>1 H oo / Γ \ a ® ° "</td><td>o, o, /. / 33 SS OO</td><td>II o, o / V- O</td><td>\</td>
<td></td><td></td><td></td><td></td><td></td><td>e</td>
<td></td><td></td><td>33 CJ</td><td>33</td><td>a</td><td>O</td>
<td></td><td></td><td>U</td><td>O</td><td>O</td><td></td>
<td>kg / ha</td><td colspan="2">0.4</td><td>0.4</td><td colspan="2">0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td></td><td>9D, 9G</td><td>9D, 9G</td><td>9C</td><td></td>
<td>cotton</td><td></td><td>6C, 9G</td><td>7C, 9G</td><td>9C</td><td></td>
<td>Morning Glory</td><td></td><td>9C</td><td>IOC</td><td>IOC</td><td></td>
<td>barnacles</td><td></td><td>6C, 9G</td><td>9C</td><td>IOC</td><td></td>
<td>Kassie</td><td></td><td>5C, 8G</td><td>5C, 8G</td><td>IOC</td><td></td>
<td>Cyprus grass</td><td></td><td>7G</td><td>8G</td><td>IOC</td><td></td>
<td>crabgrass</td><td></td><td>2A</td><td>0</td><td>5C.8G</td><td></td>
<td>barnyardgrass</td><td></td><td>9C</td><td>5C, 9H</td><td>6C, 9H</td><td></td>
<td>Wild oats</td><td></td><td>2C</td><td>8G</td><td>2C, 6G</td><td></td>
<td>wheat</td><td></td><td>IC</td><td>5C, 8G</td><td>2C</td><td></td>
<td>Corn</td><td></td><td>9H</td><td>5C.9H</td><td>IOC</td><td></td>
<td>soybeans</td><td></td><td>9C</td><td>3C, 9G</td><td>5C, 9G</td><td></td>
<td>rice</td><td></td><td>4C, 8G</td><td>5C, 9G</td><td>5C, 8G</td><td></td>
<td>sorghum</td><td></td><td>2C, 9G</td><td>3C, 9G</td><td>5C, 9G</td><td></td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>Morning Glory</td><td></td><td>9G</td><td>9G</td><td>9G</td><td></td>
<td>barnacles</td><td></td><td>9G</td><td>10E</td><td>9G</td><td></td>
<td>Kassie</td><td></td><td>8G</td><td>9G</td><td>6C, 9G</td><td></td>
<td>Cyprus grass</td><td></td><td>10E</td><td>10E</td><td>10E</td><td></td>
<td>crabgrass</td><td></td><td>0</td><td>6G</td><td>2C, 6G</td><td></td>
<td>barnyardgrass</td><td></td><td>9H</td><td>9H</td><td>2C, 9H</td><td></td>
<td>Wild oats</td><td></td><td>8G</td><td>2C, 9H</td><td>9G</td><td></td>
<td>wheat</td><td></td><td>2G</td><td>9G</td><td>5G</td><td></td>
<td>Corn</td><td></td><td>2C, 8G</td><td>2U, 9H</td><td>9G</td><td></td>
<td>soybeans</td><td></td><td>8H</td><td>9H</td><td>9H</td><td></td>
<td>rice</td><td></td><td>10E</td><td>10E</td><td>10E</td><td></td>
<td>sorghum</td><td></td><td>9G</td><td>9H</td><td>2C.9G</td><td></td>
- 36 No.371668
Table XII (continued)
<td></td><td>foi</td><td></td><td>IOI</td><td></td><td>IOI</td>
<td></td><td colspan="2">Y \</td><td></td><td>\> = O 1</td><td>Y \</td>
<td></td><td></td><td>0 = 0</td><td>I</td><td>O</td><td>0 = 0</td>
<td></td><td>d * w</td><td>O N</td><td><4 O cn 1</td><td>N</td><td><sup>N</sup> Λ o o W 1</td>
<td></td><td>i</td><td>33</td><td>33</td><td>SB</td><td>33 ~</td>
<td></td><td>2</td><td>O</td><td>2</td><td>O</td><td>2 ~</td>
<td></td><td>0 = 0</td><td>33</td><td>0 = 0</td><td>1 m</td><td>0 = 0 o 1 '</td>
<td></td><td>Ö2</td><td>O</td><td>SB</td><td>SB</td><td>33 1</td>
<td></td><td></td><td>1</td><td>2</td><td>O</td><td>T sb</td>
<td></td><td></td><td>O</td><td></td><td></td><td>Λ <sup>ü</sup></td>
<td></td><td>2<sup>Z</sup> 2 1 II</td><td></td><td>2 2</td><td></td><td>2 2 1 II</td>
<td></td><td>1 II / <sup>z</sup></td><td>\.</td><td colspan="2">Λλ</td><td>1 II / V \</td>
<td></td><td>O</td><td rowspan="2">s O</td><td>O</td><td>O</td><td>SB "</td>
<td></td><td></td><td>SB</td><td>ss</td><td>SB O</td>
<td></td><td>O</td><td></td><td>Ü</td><td>O</td><td>O</td>
<td>kg / ha</td><td colspan="2">0.4</td><td colspan="2">0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>9G</td><td></td><td>5C, 8G, 6Y</td><td></td><td>6C.6G.6Y</td>
<td>cotton</td><td>9C</td><td></td><td>2C.2H.7G</td><td></td><td>2C, 2H, 7G</td>
<td>Morning Glory</td><td>IOC</td><td></td><td>IC</td><td></td><td>2C, 8G</td>
<td>barnacles</td><td>IOC</td><td></td><td>3C, 9G</td><td></td><td>4C, 9G</td>
<td>Kassie</td><td>9C</td><td></td><td>5G</td><td></td><td>5G</td>
<td>Cyprus grass</td><td>9C</td><td></td><td>2G</td><td></td><td>7G</td>
<td>crabgrass</td><td>2C, 5G</td><td></td><td>2G</td><td></td><td>0</td>
<td>barnyardgrass</td><td>2C.8H</td><td></td><td>3C.9H</td><td></td><td>3C.9H</td>
<td>Wild oats</td><td>4G</td><td></td><td>IC</td><td></td><td>5G</td>
<td>wheat</td><td>IC</td><td></td><td>IC</td><td></td><td>3C</td>
<td>Corn</td><td>9C</td><td></td><td>3U, 9G</td><td></td><td>2C.9G</td>
<td>soybeans</td><td>6C, 9G</td><td></td><td>1H</td><td></td><td>2H.5G</td>
<td>rice</td><td>1C.7G</td><td></td><td>8G</td><td></td><td>2C, 9G</td>
<td>sorghum</td><td>2U, 9G</td><td></td><td>9G</td><td></td><td>2U, 9G</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>Morning Glory</td><td>9C</td><td></td><td>5G</td><td></td><td>8G</td>
<td>barnacles</td><td>9G</td><td></td><td>9G</td><td></td><td>9G</td>
<td>Kassie</td><td>6C.9G</td><td></td><td>5G</td><td></td><td>7G</td>
<td>Cyprus grass</td><td>9G</td><td></td><td>5G</td><td></td><td>7G</td>
<td>crabgrass</td><td>1C.3G</td><td></td><td>0</td><td></td><td>0</td>
<td>barnyardgrass</td><td>4C.9G</td><td></td><td>2C.8G</td><td></td><td>2C.9G</td>
<td>Wild oats</td><td>8H</td><td></td><td>6G</td><td></td><td>2C, 8G</td>
<td>wheat</td><td>1C, 2G</td><td></td><td>2G</td><td></td><td>8G</td>
<td>Corn</td><td>3C, 9G</td><td></td><td>2C.7G</td><td></td><td>2C.8G</td>
<td>soybeans</td><td>9H</td><td></td><td>3G</td><td></td><td>1C.3G</td>
<td>rice</td><td>9H</td><td></td><td>8G</td><td></td><td>9H</td>
<td>sorghum</td><td>2C.9G</td><td></td><td>8G</td><td></td><td>2H.8G</td>
- 37 No.371668
Table XII (continued)
<td></td><td>IOI N O £ o =; e Z \ 1 II O b ü</td><td>-0 = 0 ! O 1 9t O "4 SS O 1 n e O \ O e O</td><td>l0L<sub>= o</sub>1 o 1 9t ° Ξ- ? O EY e T 1 II O. o / V \ O '" "E E ü ü</td><td>EE ü O OO \ / X / I V | O./ o \ 1 ® 2 * 4 0 = 0W \ / (Q></td>
<td>kg / ha</td><td colspan="2">0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>6C.8G.6Y</td><td></td><td>8C, 5G, 6Y</td><td>5S, 8G, 6Y</td>
<td>cotton</td><td>2C, 2H, 8G</td><td></td><td>2C.2H.8G</td><td>3C, 3H, 9G</td>
<td>Morning Glory</td><td>1C, 8G</td><td></td><td>3C.7G</td><td>9C</td>
<td>barnacles</td><td>2C, 9G</td><td></td><td>5C, 9G</td><td>9C</td>
<td>Kassie</td><td>5G</td><td></td><td>2C.5G</td><td>IC</td>
<td>Cyprus grass</td><td>3G</td><td></td><td>2G</td><td>IC, SG</td>
<td>crabgrass</td><td>3G</td><td></td><td>0</td><td>1C.5G</td>
<td>barnyardgrass</td><td>IC</td><td></td><td>2H</td><td>5C, 9H</td>
<td>Wild oats</td><td>0</td><td></td><td>0</td><td>2C.5G</td>
<td>wheat</td><td>0</td><td></td><td>0</td><td>IC</td>
<td>Corn</td><td>6H</td><td></td><td>7H</td><td>7H</td>
<td>soybeans</td><td>7G</td><td></td><td>6H</td><td>2H.9G</td>
<td>rice</td><td>2G</td><td></td><td>6G</td><td>C</td>
<td>sorghum</td><td>7H</td><td></td><td>2C, 9G</td><td>8H</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td>
<td>Morning Glory</td><td>4G</td><td></td><td>0</td><td>8G</td>
<td>barnacles</td><td>5C.9G</td><td></td><td>5C, 9G</td><td>8G</td>
<td>Kassie</td><td>2C.SG</td><td></td><td>3C.7G</td><td>3G</td>
<td>Cyprus grass</td><td>0</td><td></td><td>2G</td><td>5G</td>
<td>crabgrass</td><td>0</td><td></td><td>2G</td><td>0</td>
<td>barnyardgrass</td><td>0</td><td></td><td>0</td><td>9H</td>
<td>Wild oats</td><td>0</td><td></td><td>0</td><td>5G</td>
<td>wheat</td><td>0</td><td></td><td>0</td><td>3G</td>
<td>Corn</td><td>2G</td><td></td><td>4G</td><td>1C.7G</td>
<td>soybeans</td><td>IC</td><td></td><td>0</td><td>2C, 4H</td>
<td>rice</td><td>0</td><td></td><td>0</td><td>9H</td>
<td>sorghum</td><td>2H</td><td></td><td>3G</td><td>8G</td>
Nr.371668
Table XII (continued) kg / ha
After sprouting
bush beans
cotton
Morning Glory
barnacles
Kassie
Cyprus grass
Pinger millet
barnyardgrass
Wild oats
wheat
Corn
soybeans
rice
sorghum
Before sprouting
Morning Glory
barnacles
Kassie
Cyprus grass
crabgrass
barnyardgrass
Wild oats
wheat
Corn
soybeans
rice
sorghum
<img file="AT371668B_D0033.tif" />
2 I
0 = 0 i
A 2 2
0.4
6C, 8G, 6Y
2H, 3C, 8G
6C, 9G
3C, 9G
5C
2G
3C.8H
6H
2H, 8G
2G
3G
9G
9C
2C
9H
2G
2G
1C, 7G
2C
5G
8G
<img file="AT371668B_D0034.tif" />
X 2 I
0 = 0
I
Ä 2 2 'V'
X
0.4
9C
9C
IOC
IOC
9C
IOC
2C.6G
3C, 9H
9G
1C, 2G
6H
5C.9G
5C.9G
3G, 9G
9G
9G
2C.9G
10E
5G
9H
9G
3G
9H
9H
10E
9H
<img file="AT371668B_D0035.tif" />
I
0 = 0
I
X
Λ
O., O <sup>z</sup>% / \
X
0.4
9C, 9G
9C, 9G
IOC
IOC
9C
6C.9G
3G
6C.9H
3C.9G
3C, 5G
9H
4C, 9G
9C
4C, 9G
9G
9H
3C.9G
10E
2C.5G
9H
9G
8H
2U.9G
9H
10E
9H
- 39 Nr.371668
Table XII (continued)
<td></td><td>r-1 O</td><td></td>
<td></td><td>|</td><td></td>
<td></td><td></td><td><f- '</td>
<td></td><td>, 101</td><td>1 ioi! ιοι</td>
<td></td><td>ϊ / Υ</td><td>/ γ? / γ</td>
<td></td><td></td><td>0 = 0 0 = 0</td>
<td></td><td>0 = 0 1</td><td></td>
<td></td><td>O</td><td>oo</td>
<td></td><td>w</td><td>ω ω</td>
<td></td><td>33</td><td>33 33</td>
<td></td><td>2</td><td>2 2</td>
<td></td><td>0 = 0</td><td>0 = 0 0 = 0</td>
<td></td><td>33</td><td></td>
<td></td><td>2</td><td>T f</td>
<td></td><td>A</td><td></td>
<td></td><td>2 2</td><td>Tu TT</td>
<td></td><td>/ V \ oo</td><td>/ v \ / v \ ο o o</td>
<td></td><td></td><td>η mn 33</td>
<td></td><td>CB B3</td><td>SB 33 SB ü</td>
<td></td><td>oo</td><td>Ο Ο O</td>
<td>kg / ha</td><td>0.4</td><td>0.4 0.4</td>
<td>After sprouting</td><td></td><td></td>
<td>bush beans</td><td>9C, 9G</td><td>5H, 8C 5C, 9H</td>
<td>cotton</td><td>7C, 9G</td><td>9C IOC</td>
<td>Morning Glory</td><td>IOC</td><td>IOC 9C</td>
<td>barnacles</td><td>IOC</td><td>10G IOC</td>
<td>Kassie</td><td>6C, 9G</td><td>9C 9C</td>
<td>Cyprus grass</td><td>IOC</td><td>9C 9C</td>
<td>crabgrass</td><td>IC</td><td>6C 3Ü, 5G</td>
<td>barnyardgrass</td><td>3G</td><td>9C IOC</td>
<td>Wild oats</td><td>0</td><td>6C 3C, 7G</td>
<td>wheat</td><td>0</td><td>3G, 4G 3C.8G</td>
<td>Corn</td><td>9H</td><td>5U, 8G 9C</td>
<td>soybeans</td><td>5C, 9G</td><td>6H.8G 5H, 9G</td>
<td>rice</td><td>2C, 9G</td><td>7C 8C</td>
<td>sorghum</td><td>8H</td><td>9C IOC</td>
<td>Before sprouting</td><td></td><td></td>
<td>Morning Glory</td><td>9G</td><td>9G 9H</td>
<td>barnacles</td><td>9G</td><td>5H, 9G 8H.9G</td>
<td>Kassie</td><td>5C, 9G</td><td>5H, 8G 8H, 9G</td>
<td>Cyprus grass</td><td>10E</td><td>10E 10E</td>
<td>crabgrass</td><td>IG</td><td>8G 8G</td>
<td>barnyardgrass</td><td>2C, 8H</td><td>5H, 9G 5H.9G</td>
<td>Wild oats</td><td>8G</td><td>7G 8G</td>
<td>wheat</td><td>IC</td><td>7G 9G</td>
<td>Corn</td><td>2C, 9H</td><td>5H, 9G 7H.9G</td>
<td>soybeans</td><td>9H</td><td>6H, 8G 8H.9G</td>
<td>rice</td><td>10E</td><td>10E 10E</td>
<td>sorghum</td><td>9H</td><td>5H, 9G 8H, 9G</td>
Nr.371668
Table XII (continued)
<td></td><td>0)</td><td></td><td colspan="2">s " ο Y \</td>
<td></td><td colspan="2">8 IO J / γ O<sup>N</sup>w</td><td colspan="2">O> - '<sup>os</sup>-<sup>ε</sup>€ 'ηο) -cyd II 0</td>
<td></td><td></td><td>e</td><td colspan="2">e 2</td>
<td></td><td></td><td>ο = ώ</td><td>o =</td><td>J</td>
<td></td><td></td><td>EB</td><td></td><td>s z</td>
<td></td><td></td><td>2 2</td><td colspan="2">2 2 1 II</td>
<td></td><td colspan="2">k ä / <sup>2</sup> \ oo</td><td colspan="2">Ck O / V \ oo</td>
<td></td><td>e ü</td><td>e ü</td><td>G</td><td></td>
<td>kg / ha</td><td colspan="2">0.4</td><td>2</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td></td><td>8H.9G</td><td>3C.9G.9D</td><td>3C.9G.9D</td>
<td>cotton</td><td></td><td>9C</td><td>9C</td><td>4C.9G</td>
<td>Morning Glory</td><td></td><td>IOC</td><td>IOC</td><td>9C</td>
<td>barnacles</td><td></td><td>IOC</td><td>9C</td><td>9C</td>
<td>Kassie</td><td></td><td>9C</td><td>9C</td><td>3C.7G</td>
<td>Cyprus grass</td><td></td><td>9C</td><td>9C</td><td>2C.6G</td>
<td>crabgrass</td><td></td><td>6G</td><td>4C.7G</td><td>2C.6G</td>
<td>barnyardgrass</td><td></td><td>8C</td><td>IOC</td><td>9C</td>
<td>Wild oats</td><td></td><td>2C</td><td>9C</td><td>2C, 5G</td>
<td>wheat</td><td></td><td>2C</td><td>9C</td><td>1C, 4G</td>
<td>Corn</td><td></td><td>5H, 7G</td><td>9C</td><td>2U.8H</td>
<td>soybeans</td><td></td><td>5H, 8G</td><td>6C, 9G</td><td>6C, 9G</td>
<td>rice</td><td></td><td>8C</td><td>9C</td><td>6C, 8G</td>
<td>sorghum</td><td></td><td>2H, 7G</td><td>9C</td><td>3C.8G</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td>
<td>Morning Glory</td><td></td><td>8H.9G</td><td>5C, 9G</td><td>9G</td>
<td>barnacles</td><td></td><td>8H.9G</td><td>9G</td><td>9G</td>
<td>Kassie</td><td></td><td>8H.8G</td><td>9C</td><td>9G</td>
<td>Cyprus grass</td><td></td><td>9E.9G</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td></td><td>7G</td><td>7G</td><td>8G</td>
<td>barnyardgrass</td><td></td><td>5H, 9G</td><td>9H</td><td>9H</td>
<td>Wild oats</td><td></td><td>8G</td><td>8G</td><td>7G</td>
<td>wheat</td><td></td><td>7G</td><td>9G</td><td>9G</td>
<td>Corn</td><td></td><td>7H.SG</td><td>9G</td><td>2C, 9G</td>
<td>soybeans</td><td></td><td>7H.8G</td><td>9H</td><td>7H</td>
<td>rice</td><td></td><td>7E.8G</td><td>10E</td><td>10E</td>
<td>sorghum</td><td></td><td>7H.9G</td><td>SH</td><td>9H</td>
Nr.371668
Table XII (continued)
<td></td><td colspan="2">Σ32 1 ioi ? / Y 0 = 0 N O ss z A zz O / <sup>s </sup>n s ss o ü</td><td>IOI 1 o = o 1 O d * φ ss § o Ä zz 1 II AA oo ss ss ü ü</td>
<td>kg / ha</td><td>2</td><td>0.4</td><td>2</td>
<td>After sprouting bush beans cotton Morning Glory barnacles Kassie Cyprus grass crabgrass barnyardgrass Wild oats wheat Corn soybeans rice sorghum</td><td>3C, 9G, 10D 5C.9G IOC IOC 9C 9C 5C, 8G IOC 4C, 8G 8C 9C 9C 8C 9C</td><td>3C, 9G, 9D 5C.9G 9C 9C 3C, 7G 2C.7G 3G IOC 8G 4C, 8G 5C, 9G 4C.8G 5C, 8G 2C, 8G</td><td>9G.10D 9C IOC 9C 9C 9C 9C IOC 9C 9C 9C 6C, 9G 9C IOC</td>
<td>Before sprouting Morning Glory barnacles Kassie Cyprus grass crabgrass barnyardgrass Wild oats wheat Corn soybeans rice sorghum</td><td>5C, 9H 9G 3C.9G 10E 3C.9G 9H 3C, 9G 9H 9G 9H 10E 9H</td><td>9G 9G 9G 10E 7G 9H 2C, 8G 9H 9G 9H 10E 9H</td><td>10E 9G 9G 10E 9H 9H 2C.9G 9H 10E 9H 10E 10H</td>
- 42 No.371668
Table XII (continued)
<td></td><td>- <O> -Z " II 0</td><td colspan="2">EE 0 0 \ / \ / 101 2 ^^, 2</td>
<td></td><td>1 o</td><td></td><td></td>
<td></td><td>0 II -C-NH-SO<sup>c</sup>2h<sub>5</sub>-</td><td>-HN-O-1 II O</td><td></td>
<td></td><td>2</td><td colspan="2">2</td>
<td></td><td>Λ 2 2</td><td colspan="2">O § <z> O io □</td>
<td></td><td>II 1 o, o / v<sup>z</sup> \ oo</td><td colspan="2">A / 101</td>
<td></td><td>JE ffi oo</td><td></td><td></td>
<td>kg / ha</td><td>0.4</td><td>2</td><td>2</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>3C, 9G, 9D</td><td>5H, 8G, 6F</td><td>IC</td>
<td>cotton</td><td>9C</td><td>4C, 7G</td><td></td>
<td>Morning Glory</td><td>IOC</td><td>4G</td><td>0</td>
<td>barnacles</td><td>9C</td><td>8C</td><td>0</td>
<td>Kassie</td><td>9G</td><td>3C, 8G</td><td>0</td>
<td>Cyprus grass</td><td>9C</td><td>8C</td><td>0</td>
<td>crabgrass</td><td>4C.7G</td><td>5G</td><td>0</td>
<td>barnyardgrass</td><td>IOC</td><td>8C</td><td>1H</td>
<td>Wild oats</td><td>9C</td><td>4C</td><td>0</td>
<td>wheat</td><td>9C</td><td>4C</td><td>0</td>
<td>Corn</td><td>9C</td><td>3H, 8G</td><td>0</td>
<td>soybeans</td><td>6C, 9G</td><td>6H, 9G</td><td>IC</td>
<td>rice</td><td>9C</td><td>9C</td><td>3G</td>
<td>sorghum</td><td>9C</td><td>3H, 8G</td><td>1C, 5G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>Morning Glory</td><td>10E</td><td>7G</td><td>IC</td>
<td>barnacles</td><td>9G</td><td>5H, 8G</td><td>IC</td>
<td>Kassie</td><td>9G</td><td>5H.8G</td><td>IC</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td>0</td>
<td>crabgrass</td><td>3C, 9G</td><td>2G</td><td>0</td>
<td>barnyardgrass</td><td>9H</td><td>5H, 8G</td><td>0</td>
<td>Wild oats</td><td>9G</td><td>5H, 7G</td><td>0</td>
<td>wheat</td><td>9H</td><td>5H.8G</td><td>0</td>
<td>Corn</td><td>10E</td><td>5H.9G</td><td>3G</td>
<td>soybeans</td><td>9H</td><td>5H.8G</td><td>IC</td>
<td>rice</td><td>10E</td><td>8H, 9G</td><td>0</td>
<td>sorghum</td><td>9H</td><td>5H.8G</td><td>0</td>
- 43 Nr.371668
Table XII (continued)
<td></td><td><O> -</td><td>- SO-NH2 COOH</td><td>0 II C-NH-</td><td>/<sup>CH</sup>3 N \ <O><sup>N</sup>~ X,</td>
<td>kg / ha</td><td>10</td><td>2</td><td>2</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>2C, 2H</td><td>IC</td><td>0</td><td>0</td>
<td>cotton</td><td></td><td></td><td>0</td><td>0</td>
<td>Morning Glory</td><td>0</td><td>0</td><td>0</td><td>0</td>
<td>barnacles</td><td>0</td><td>0</td><td>0</td><td>0</td>
<td>Kassi.e</td><td>0</td><td>IC</td><td>0</td><td>0</td>
<td>Cyprus grass</td><td>0</td><td>0</td><td>0</td><td>0</td>
<td>crabgrass</td><td>0</td><td>0</td><td>0</td><td>2G</td>
<td>barnyardgrass</td><td>2G</td><td>0</td><td>0</td><td>1C.2H</td>
<td>Wild oats</td><td>0</td><td>0</td><td>0</td><td>0</td>
<td>wheat</td><td>0</td><td>0</td><td>0</td><td>0</td>
<td>Corn</td><td>0</td><td>0</td><td>0</td><td>0</td>
<td>Soy bean</td><td>IC</td><td>0</td><td>0</td><td>0</td>
<td>rice</td><td>5G</td><td>0</td><td>0</td><td>0</td>
<td>sorghum</td><td>3G</td><td>0</td><td>0</td><td>0</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td>
<td>Morning Glory</td><td>7G</td><td>IC</td><td>0</td><td>0</td>
<td>barnacles</td><td>9G</td><td>0</td><td>0</td><td>0</td>
<td>Kassie</td><td>1C.5G</td><td>IC</td><td>0</td><td>0</td>
<td>Cyprus grass</td><td>9G</td><td>9G</td><td>0</td><td>0</td>
<td>crabgrass</td><td>IC</td><td>0</td><td>0</td><td>0</td>
<td>barnyardgrass</td><td>1C, 3G</td><td>0</td><td>0</td><td>0</td>
<td>Wild oats</td><td>1G.5G</td><td>0</td><td>0</td><td>0</td>
<td>wheat</td><td>2C, 7G</td><td>3G</td><td>0</td><td>0</td>
<td>Corn</td><td>8G</td><td>3G</td><td>0</td><td>0</td>
<td>soybeans</td><td>4G</td><td>0</td><td>0</td><td>0</td>
<td>rice</td><td>2C, 7G</td><td>0</td><td>0</td><td>0</td>
<td>sorghum</td><td>5G</td><td>0</td><td>0</td><td>0</td>
- 44 Nr.371668
Table XII (continued) • \ z
II Ί
Second χίί<sup>2</sup>
<td colspan="2">r \ \ /</td><td>ί</td>
<td>c</td><td>></td><td>33 2 0 = 0 ffi 2</td>
<td>/ 0</td><td></td><td>O w</td>
0 = 0th
B
I
0 = 0
B
N ow / ρλ \ y / \ _ / \ Q /
<td>kg / ha</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>9C</td>
<td>cotton</td><td>5C.9G</td><td>5C.9G</td>
<td>Morning Glory</td><td>9C</td><td>5C.9G</td>
<td>barnacles</td><td>5C, 9G</td><td>6G</td>
<td>Kassie</td><td>5C, 9G</td><td>9C</td>
<td>Cyprus grass</td><td>3C, 8G</td><td>4G</td>
<td>crabgrass</td><td>2C, 8G</td><td>3G</td>
<td>barnyardgrass</td><td>9G</td><td>2G</td>
<td>Wild oats</td><td>7C</td><td>0</td>
<td>wheat</td><td>7C</td><td>2G</td>
<td>Corn</td><td>5U.9C</td><td>8G</td>
<td>soybeans</td><td>9C</td><td>9C</td>
<td>rice</td><td>5C.8G</td><td>2C, 5G</td>
<td>sorghum</td><td>9C</td><td>1C, 9G</td>
<td>Before sprouting</td><td></td><td></td>
<td>Morning Glory</td><td>9G</td><td>8G</td>
<td>barnacles</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>9G</td><td>9G</td>
<td>Cyprus grass</td><td>10E</td><td>2G</td>
<td>crabgrass</td><td>4C, 9G</td><td>5G</td>
<td>barnyardgrass</td><td>9H</td><td>5G</td>
<td>Wild oats</td><td>2C, 8G</td><td>2G</td>
<td>wheat</td><td>9H</td><td>0</td>
<td>Corn</td><td>10E</td><td>2C, 7G</td>
<td>soybeans</td><td>SH</td><td>2C, 4H</td>
<td>rice</td><td>10E</td><td>2C.5G</td>
<td>sorghum</td><td>10E</td><td>8G</td>
Nr.371668
Table XII (continued)
<td></td><td>X OX oo \ ^ \ /</td>
<td></td><td></td>
<td></td><td>X</td>
<td></td><td>0 = 0 0 § 0 = 0 « \ / \ 0)</td>
<td></td><td>/ tu</td>
<td>kg / ha</td><td>0.4</td>
<td>After sprouting</td><td></td>
<td>bush beans</td><td>9C</td>
<td>cotton</td><td>5C.9G</td>
<td>Morning Glory</td><td>9C</td>
<td>barnacles</td><td>3H, 9G</td>
<td>Kassie</td><td>9C</td>
<td>Cyprus grass</td><td>6C.9G</td>
<td>crabgrass</td><td>9C</td>
<td>barnyardgrass</td><td>5C.8H</td>
<td>Wild oats</td><td>0</td>
<td>wheat</td><td>0</td>
<td>Corn</td><td>9C</td>
<td>soybeans</td><td>5C.9G</td>
<td>rice</td><td>9C</td>
<td>sorghum</td><td>2C.9G</td>
<td>Before sprouting</td><td></td>
<td>Morning Glory</td><td>9G</td>
<td>barnacles</td><td>10E</td>
<td>Kassie</td><td>9G</td>
<td>Cyprus grass</td><td>10E</td>
<td>crabgrass</td><td>5G</td>
<td>barnyardgrass</td><td>2C, 8G</td>
<td>Wild oats</td><td>2G</td>
<td>wheat</td><td>0</td>
<td>Corn</td><td>-</td>
<td>soybeans</td><td>9H</td>
<td>rice</td><td>9H</td>
<td>sorghum</td><td>9G</td>
Nr.371668
Table XII (continued)
<td></td><td>EC O 93 oo \ Z \ / 1 II</td><td>i "l O ü \ ^ \ /</td>
<td></td><td><n S □ 3 2 O 0 = 0 O 33 / o 0 = 0 m \ _ / <0></td><td>33 1 C4 O oi »EC SB 2 «0 = 0 O SB OZ / o * 0 = 0 m \ __ /</td>
<td></td><td>/ \ F- »<-1 oo</td><td>/ Q \</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td>
<td>bush beans</td><td>4C, 9G, 6Y</td><td>3C.5G.6Y</td>
<td>cotton</td><td>2C, 3H</td><td>IG</td>
<td>Morning Glory</td><td>5C.8G</td><td>0</td>
<td>barnacles</td><td>3C.8G</td><td>5C</td>
<td>Kassie</td><td>2C</td><td>0</td>
<td>Cyprus grass</td><td>6G</td><td>0</td>
<td>crabgrass</td><td>2G</td><td>2C</td>
<td>barnyardgrass</td><td>7H</td><td>2C.6G</td>
<td>Wild oats</td><td>0</td><td>IC</td>
<td>wheat</td><td>0</td><td>2G</td>
<td>Corn</td><td>2G</td><td>1C.7G</td>
<td>soybeans</td><td>5C, 7G</td><td>1G, 5G</td>
<td>rice</td><td>2C</td><td>2C, 4G</td>
<td>sorghum</td><td>5G</td><td>2C.7G</td>
<td>Before sprouting</td><td></td><td></td>
<td>Morning Glory</td><td>8G</td><td>3G</td>
<td>barnacles</td><td>8G</td><td>-</td>
<td>Kassie</td><td>0</td><td>0</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td>2G</td><td>2G</td>
<td>barnyardgrass</td><td>9G</td><td>1C, 8H</td>
<td>Wild oats</td><td>4G</td><td>0</td>
<td>wheat</td><td>5G</td><td>0</td>
<td>Corn</td><td>2C, 7G</td><td>IC</td>
<td>Soy bean</td><td>1C, 5H</td><td>0</td>
<td>rice</td><td>9H</td><td>8H</td>
<td>sorghum</td><td>2C, 9G '</td><td>8G</td>
- 47 No.371668
Table XII (continued)
<td rowspan="2"></td><td colspan="2">tc O O</td><td rowspan="2">x " O - / 2</td><td rowspan="2">N 33 O II " O 1 N 33 O 33 O "1 33 33 0 - 0 1 O 0 = 0 \ / \</td><td rowspan="2">e Ο E OO 1 II 2 E 0 = 0 e 2 1 CS O CO / Q></td>
<td>Λ O ec □ = / / \</td><td>33 2 0 = 0 33 2 O" m Q)</td>
<td>kg / ha</td><td colspan="3">0.4</td><td colspan="2">0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td></td><td>9C</td><td></td><td></td><td>9C</td>
<td>cotton</td><td></td><td>9C</td><td></td><td></td><td>9C</td>
<td>Morning Glory</td><td></td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>barnacles</td><td></td><td>9C</td><td></td><td></td><td>IOC</td>
<td>Kassie</td><td></td><td>9C</td><td></td><td></td><td>9C</td>
<td>Cyprus grass</td><td colspan="2">2C, 8G</td><td></td><td></td><td>7G</td>
<td>crabgrass</td><td colspan="2">2C, 8G</td><td></td><td></td><td>, 9C</td>
<td>barnyardgrass</td><td colspan="2">5C, 9H</td><td></td><td></td><td>6C, 9H</td>
<td>Wild oats</td><td colspan="2">1C.8G</td><td></td><td></td><td>2C, 7G</td>
<td>wheat</td><td colspan="2">IC, 7G</td><td></td><td></td><td>2C, 6G</td>
<td>Corn</td><td colspan="2">IOC</td><td></td><td></td><td>9C</td>
<td>soybeans</td><td colspan="2">2C.8G</td><td></td><td></td><td>9C</td>
<td>rice</td><td colspan="2">3C, 8G</td><td></td><td></td><td>5C, 8G</td>
<td>sorghum</td><td colspan="2">2C, 8G</td><td></td><td></td><td>2C, 8G</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>Morning Glory</td><td></td><td>9G</td><td></td><td></td><td>9G</td>
<td>barnacles</td><td></td><td>9G</td><td></td><td></td><td>9G</td>
<td>Kassie</td><td></td><td>9G</td><td></td><td></td><td>9G</td>
<td>Cyprus grass</td><td></td><td>8G</td><td></td><td></td><td>9G</td>
<td>crabgrass</td><td colspan="2">2C.9G</td><td></td><td></td><td>1C.8G</td>
<td>barnyardgrass</td><td></td><td>9H</td><td></td><td></td><td>2C, 9H</td>
<td>Wild oats</td><td colspan="2">1C, 7G</td><td></td><td></td><td>1C, 8G</td>
<td>wheat</td><td colspan="2">1C, 5G</td><td></td><td></td><td>7G</td>
<td>Corn</td><td colspan="2">1C, 9G</td><td></td><td></td><td>2C, 9G</td>
<td>soybeans</td><td></td><td>9H</td><td></td><td></td><td>9H</td>
<td>rice</td><td colspan="2">10E</td><td></td><td></td><td>10E</td>
<td>sorghum</td><td colspan="2">2C, 9G</td><td></td><td></td><td>9H</td>
Nr.371668
Table XII (continued)
<img file="AT371668B_D0036.tif" />
<td>kg / ha</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>9C</td>
<td>cotton</td><td>9C</td><td>5C.9G</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>9C</td><td>9C</td>
<td>Kassie</td><td>9C</td><td>IOC</td>
<td>Cyprus grass</td><td>4G</td><td>7G</td>
<td>crabgrass</td><td>1C, 5G</td><td>9C</td>
<td>barnyardgrass</td><td>6C.9H</td><td>9C</td>
<td>Wild oats</td><td>4G</td><td>3C, 7G</td>
<td>wheat</td><td>2G</td><td>3C.6G</td>
<td>Corn</td><td>9C</td><td>9C</td>
<td>soybeans</td><td>6C, 9G</td><td>-</td>
<td>rice</td><td>5C.9G</td><td>-</td>
<td>sorghum</td><td>1C.8G</td><td>5C.9G</td>
<td>Before sprouting</td><td></td><td></td>
<td>Morning Glory</td><td>3C.9G</td><td>9G</td>
<td>barnacles</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>8G</td><td>10E</td>
<td>Cyprus grass</td><td>7G</td><td>10E</td>
<td>crabgrass</td><td>5G</td><td>2C.9G</td>
<td>barnyardgrass</td><td>9H</td><td>9H</td>
<td>Wild oats</td><td>7G</td><td>9H</td>
<td>wheat</td><td>5G</td><td>9H</td>
<td>Corn</td><td>1U.9G</td><td>9H</td>
<td>soybeans</td><td>9H</td><td>9H</td>
<td>rice</td><td>9H</td><td>10E</td>
<td>sorghum</td><td>1C.9G</td><td>9H</td>
- 49 No.371668
Table XII (continued)
<td></td><td>33 » O 33 oo "1 II 33 Zx 2 ü N CG O<sup>Λ</sup> N 33 33 1 ο O ® | Z 33 ffi 0 = 0 0-0 pounds i 2 O * 1 O 0 = 0 w \ / (Q)</td><td>rt "33 33 ü OO \ ^<sup>2</sup>\ / O N 33 O g 33 33 0 = 0 o-o 5 i 2 ON 1 o 0 = 0 CO \ _ / / Q \ \ R /</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td>
<td>After sprouting bush beans cotton Morning Glory barnacles Kassie Cyprus grass crabgrass barnyardgrass Wild oats wheat Corn soybeans rice sorghum</td><td>9C 6C, 9G IOC IOC 9C 1C, 8G 3C 9C 1C.2G 1C, 4G 9C 9C 5C, 9G</td><td>9C 4C, 9G IOC 9C 5C, 9G 2C, 8G 2C, 6G 3C, 9H 3G 2G 3R, 8G 5C, 9G 3C, 7G 2G, 8G</td>
<td>Before sprouting Morning Glory barnacles Kassie Cyprus grass crabgrass barnyardgrass Wild oats wheat Corn soybeans rice sorghum</td><td>9G 8G 8G 5G 0 9H 5G 3G 8G 9H 9H 2C.9G</td><td>9G 9G 8G 2C, 9G 2C, 8G 2C, 9H 2C, 8G 4G 9G 9H 9H 9H</td>
- 50 No.371668
Table XII (continued) z \ y> O '\ z
X
0 = 0
X
N o
Where
I o
M ü x<sup>N </sup>O
I o-o //
X
0 = 0
X o
w / F \
<img file="AT371668B_D0037.tif" />
\O/
<td>kg / ha</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td>
<td>bush beans</td><td>5C, 8G, 6Y</td><td>9C</td>
<td>cotton</td><td>5C, 9G</td><td>9C</td>
<td>Morning Glory</td><td>9C</td><td>9C</td>
<td>barnacles</td><td>5C, 9G</td><td>IOC</td>
<td>Kassie</td><td>5C, 9G</td><td>5C, 9G</td>
<td>Cyprus grass</td><td>0</td><td>8G</td>
<td>crabgrass</td><td>5C.8G</td><td>4G</td>
<td>barnyardgrass</td><td>3C, 7H</td><td>9G</td>
<td>Wild oats</td><td>2C</td><td>1C.2G</td>
<td>wheat</td><td>0</td><td>1C, 2G</td>
<td>Corn</td><td>8U.9G</td><td>5U, 9H</td>
<td>soybeans</td><td>5C, 8G</td><td>9C</td>
<td>rice</td><td>3C.8G</td><td>3C.8G</td>
<td>sorghum</td><td>2C.9G</td><td>8G</td>
<td>Before sprouting</td><td></td><td></td>
<td>Morning Glory</td><td>9G</td><td>9C</td>
<td>barnacles</td><td>8G</td><td>9G</td>
<td>Kassie</td><td>8G</td><td>3C, 8G</td>
<td>Cyprus grass</td><td>9G</td><td>10E</td>
<td>crabgrass</td><td>2C.8H</td><td>2C.8G</td>
<td>barnyardgrass</td><td>2C.9H</td><td>5C, 9H</td>
<td>Wild oats</td><td>4G</td><td>1C.8G</td>
<td>wheat</td><td>0</td><td>9H</td>
<td>Corn</td><td>2C.8G</td><td>9G</td>
<td>soybeans</td><td>7H</td><td>9H</td>
<td>rice</td><td>9H</td><td>10E</td>
<td>sorghum</td><td>1C.9G</td><td>5C.9H</td>
- 51 No.371668
Table XII (continued)
<img file="AT371668B_D0038.tif" />
<td>kg / ha</td><td>0.4</td><td>0.4</td>
<td>After sprouting bush beans</td><td>9C</td><td>6C.9G</td>
<td>cotton</td><td>2C, 2H, 5G</td><td>4C.9G</td>
<td>Morning Glory</td><td>9C</td><td>IOC</td>
<td>barnacles</td><td>9G</td><td>9C</td>
<td>Kassie</td><td>9C</td><td>9C</td>
<td>Cyprus grass</td><td>9G</td><td>9C</td>
<td>crabgrass</td><td>5C.8H</td><td>IOC</td>
<td>barnyardgrass</td><td>6C, 9H</td><td>9C</td>
<td>Wild oats</td><td>4C.8G</td><td>9C</td>
<td>wheat</td><td>2C, 8G</td><td>6C, 8G</td>
<td>Corn</td><td>2C, 9H</td><td>5U, 9C</td>
<td>Soy bean</td><td>2C, 8G</td><td>9C</td>
<td>rice</td><td>3C.8G</td><td>5C, 9G</td>
<td>sorghum</td><td>2U, 9G</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td>
<td>Morning Glory</td><td>9G</td><td>9G</td>
<td>barnacles</td><td>9G</td><td>8G</td>
<td>Kassie</td><td>9G</td><td>9G</td>
<td>Cyprus grass</td><td>1C.9G</td><td>10E</td>
<td>crabgrass</td><td>2C, 9G</td><td>9H</td>
<td>barnyardgrass</td><td>6C.9H</td><td>9H</td>
<td>Wild oats</td><td>2C.8G</td><td>2C, 8G</td>
<td>wheat</td><td>9G</td><td>9H</td>
<td>Corn</td><td>2C, 8G</td><td>9H</td>
<td>soybeans</td><td>9H</td><td>9H</td>
<td>rice</td><td>9H</td><td>10E</td>
<td>sorghum</td><td>4C, 9H</td><td>9H</td>
- 52 No.371668
Table XII (continued)
<img file="AT371668B_D0039.tif" />
ü
X o
ix
2-O
<img file="AT371668B_D0040.tif" />
<img file="AT371668B_D0041.tif" />
<img file="AT371668B_D0042.tif" />
<img file="AT371668B_D0043.tif" />
X
O
X
2-O
<img file="AT371668B_D0044.tif" />
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>10D.9G</td><td>9C</td>
<td>cotton</td><td>9C</td><td>6C.9G</td><td>IOC</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>9C</td><td>5C, 9G</td><td>9C</td>
<td>Kassie</td><td>6C.9G</td><td>9C</td><td>9C</td>
<td>Cyprus grass</td><td>6C, 9G</td><td>7C, 9G</td><td>IOC</td>
<td>crabgrass</td><td>4C.8G</td><td>5C, 8G</td><td>9C</td>
<td>barnyardgrass</td><td>9C</td><td>IOC</td><td>9C</td>
<td>Wild oats</td><td>9G</td><td>9C</td><td>9C</td>
<td>wheat</td><td>9G</td><td>9C</td><td>9C</td>
<td>Corn</td><td>IOC</td><td>9C</td><td>IOC</td>
<td>soybeans</td><td>9C</td><td>9C</td><td>9C</td>
<td>rice</td><td>6C, 8G</td><td>9C</td><td>5C, 9G</td>
<td>sorghum</td><td>9C</td><td>9C</td><td>IOC</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>10E</td>
<td>barnacles</td><td>8G: 1</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>9G '</td><td>9G</td><td>9G</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td>3C, 9G</td><td>2C, 9G</td><td>1C.9G</td>
<td>barnyardgrass</td><td>9H</td><td>9H</td><td>1C, 9H</td>
<td>Wild oats</td><td>3C</td><td>2C, 9G</td><td>2C, 9H</td>
<td>wheat</td><td>9H</td><td>9H</td><td>9H</td>
<td>Corn</td><td>1C.9G</td><td>9H</td><td>10E</td>
<td>soybeans</td><td>9H</td><td>9H</td><td>9H</td>
<td>rice</td><td>10E</td><td>10E</td><td>10E</td>
<td>sorghum</td><td>5C.9H</td><td>9H</td><td>10E</td>
- 53 No.371668
Table XII (continued)
<td></td><td>n X m OX OQ EC * o X<sup>o ==</sup>s NZ X « oo ϊ! O<sup>w</sup>X II 1 z o \ A IC) |</td><td>x O N O nm O X XX 0 O - ü 1 1 oo \ Χ \ /<sup>z</sup>w<sup>z</sup>X 0 = 1 «z S n 8-o 8 II 1 \ A</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td>
<td>After sprouting bush beans cotton Morning Glory barnacles Kassie Cyprus grass crabgrass barnyardgrass Wild oats wheat Corn soybeans rice sorghum</td><td>8C, 9G 6C, 9G 9C 2H.BG 5C.9G 9G 2G.6G 4C.9H 2G.6G 3C.5G 5U.9G 9C 5C.9G 3C, 9H</td><td>9C 6C.9G 9C 5C.9G 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C</td>
<td>Before sprouting Morning Glory barnacles Kassie Cyprus grass crabgrass barnyardgrass Wild oats wheat Corn So abjhnen rice sorghum</td><td>9G 8G 8G 10E 2C.5H 9H 6G 6G 8G 2C, 5H 9H 1C, 9G</td><td>10E 10E 3C.9G 10E 5C.9G 5C.9H 5C, 9H 10E 10H 9H 10E 10H</td>
- 54 No.371668
Table XII (continued)
<img file="AT371668B_D0045.tif" />
kg / ha 0.4 0.4
After sprouting
<td>bush beans</td><td>4C.7G.6G</td><td>9C</td>
<td>cotton</td><td>2C</td><td>9C</td>
<td>Morning Glory</td><td>2C</td><td>IOC</td>
<td>barnacles</td><td>2C, 5G</td><td>9C</td>
<td>Kassie</td><td>IC</td><td>9C</td>
<td>Cyprus grass</td><td>1C, 5G</td><td>8G</td>
<td>crabgrass</td><td>0</td><td>3C, 9G</td>
<td>barnyardgrass</td><td>3C</td><td>IOC</td>
<td>Wild oats</td><td>0</td><td>9C</td>
<td>wheat</td><td>0</td><td>9C</td>
<td>Corn</td><td>1C, 7H</td><td>9C</td>
<td>soybeans</td><td>2C</td><td>9C</td>
<td>rice</td><td>2C, 7G</td><td>IOC</td>
<td>sorghum</td><td>1C.5G</td><td>IOC</td>
<td>Before sprouting</td><td></td><td></td>
<td>Morning Glory</td><td>0</td><td>9G</td>
<td>barnacles</td><td>0</td><td>9G</td>
<td>Kassie</td><td>0</td><td>8G</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td>
<td>crabgrass</td><td>0</td><td>2C, 9G</td>
<td>barnyardgrass</td><td>2G</td><td>2C, 9H</td>
<td>Wild oats</td><td>0</td><td>2C, 7G</td>
<td>wheat</td><td>0</td><td>9H</td>
<td>Corn</td><td>1C, 4G</td><td>9G</td>
<td>soybeans</td><td>0</td><td>9H</td>
<td>rice</td><td>8H</td><td>10E</td>
<td>sorghum</td><td>3G</td><td>9H</td>
- 55 No.371668
Table XII (continued)
<td></td><td colspan="2">W ü □</td><td>33 O O y /</td><td colspan="2">33 O O N 33 Ο M SB □ V</td><td>m 33 O O<sup>S</sup>\ / II</td><td colspan="2">n / A O O V</td><td>sf O \ / II</td>
<td></td><td></td><td></td><td></td><td></td><td></td><td>II</td><td></td><td></td><td>II /<sup>2</sup></td>
<td></td><td></td><td>a</td><td></td><td></td><td>a</td><td></td><td></td><td>3</td><td></td>
<td></td><td></td><td colspan="2">&</td><td></td><td colspan="2">z</td><td></td><td colspan="2">Z</td>
<td></td><td></td><td colspan="2">0 = 0</td><td></td><td colspan="2">0 = 0</td><td></td><td colspan="2">0 = 0</td>
<td></td><td></td><td colspan="2"></td><td></td><td colspan="2">SB</td><td>35</td><td colspan="2">sn</td>
<td></td><td></td><td colspan="2">z</td><td></td><td colspan="2">z</td><td><0</td><td colspan="2">z</td>
<td></td><td></td><td></td><td></td><td></td><td></td><td>N</td><td>O</td><td></td><td>N</td>
<td></td><td></td><td colspan="2">O</td><td>B "</td><td colspan="2">O</td><td>N</td><td colspan="2">O</td>
<td></td><td>SB</td><td colspan="2">o «</td><td rowspan="2">OCH 1</td><td colspan="2">o »</td><td>X fl</td><td colspan="2">ow</td>
<td></td><td>O O-</td><td>II •O</td><td></td><td>•O</td><td></td><td>w</td><td>-O</td><td></td>
<td></td><td></td><td colspan="2">\ Ä</td><td></td><td colspan="2">\ Ä</td><td></td><td>V</td><td></td>
<td></td><td></td><td colspan="2">IOI</td><td></td><td colspan="2">IOI</td><td></td><td colspan="2">IOI</td>
<td></td><td></td><td colspan="2">\ /</td><td></td><td colspan="2">V</td><td></td><td></td><td></td>
<td>kg / ha</td><td colspan="3">0.4</td><td colspan="3">0.4</td><td colspan="3">0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td></td><td colspan="2">9C</td><td></td><td>9C</td><td></td><td></td><td>9C</td><td></td>
<td>cotton</td><td></td><td colspan="2">9C</td><td></td><td>9C</td><td></td><td></td><td>9C</td><td></td>
<td>Morning Glory</td><td></td><td colspan="2">IOC</td><td></td><td>IOC</td><td></td><td></td><td>IOC</td><td></td>
<td>barnacles</td><td></td><td colspan="2">IOC</td><td></td><td colspan="2">2C, 8G</td><td></td><td>9C</td><td></td>
<td>Kassie</td><td></td><td colspan="2">IOC</td><td></td><td colspan="2">3C, 8G</td><td></td><td>9C</td><td></td>
<td>Cyprus grass</td><td></td><td colspan="2">5C, 9G</td><td></td><td colspan="2">1C.8G</td><td></td><td>2C, 9G</td><td></td>
<td>crabgrass</td><td></td><td colspan="2">3G</td><td></td><td>9C</td><td></td><td></td><td>1C, 8G</td><td></td>
<td>barnyardgrass</td><td></td><td colspan="2">6C, 9H</td><td></td><td colspan="2">5C.8H</td><td></td><td>9C</td><td></td>
<td>Wild oats</td><td></td><td colspan="2">3C, 7G</td><td></td><td colspan="2">1C.5G</td><td></td><td>4C, 7G</td><td></td>
<td>wheat</td><td></td><td>2C,</td><td>6G</td><td></td><td>IC</td><td></td><td></td><td>4C, 6G</td><td></td>
<td>Corn</td><td></td><td colspan="2">IOC</td><td></td><td>9C</td><td></td><td></td><td>9C</td><td></td>
<td>soybeans</td><td></td><td>6C,</td><td>9G</td><td></td><td>9C</td><td></td><td></td><td>8C</td><td></td>
<td>rice</td><td></td><td>-</td><td></td><td></td><td colspan="2">5C, 9G</td><td></td><td>5C, 9G</td><td></td>
<td>sorghum</td><td></td><td>2C,</td><td>9G</td><td></td><td colspan="2">3C, 9G</td><td></td><td>3C, 9G</td><td></td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>Morning Glory</td><td></td><td colspan="2">9G</td><td></td><td>9G</td><td></td><td></td><td>9G</td><td></td>
<td>barnacles</td><td></td><td colspan="2">9G</td><td></td><td>9G</td><td></td><td></td><td>8G</td><td></td>
<td>Kassie</td><td></td><td colspan="2">9G</td><td></td><td colspan="2">2C.8G</td><td></td><td>9G</td><td></td>
<td>Cyprus grass</td><td></td><td colspan="2">10E</td><td></td><td colspan="2">1C, 9G</td><td></td><td>10E</td><td></td>
<td>crabgrass</td><td></td><td colspan="2">2G</td><td></td><td colspan="2">1C, 5G</td><td></td><td>2C, 9G</td><td></td>
<td>barnyardgrass</td><td></td><td>2C,</td><td>9H</td><td></td><td colspan="2">2C, 9H</td><td></td><td>4C, 9H</td><td></td>
<td>Wild oats</td><td></td><td colspan="2">1C, 7G</td><td></td><td colspan="2">2C.8G</td><td></td><td>2C, 7G</td><td></td>
<td>wheat</td><td></td><td colspan="2">6G</td><td></td><td>6G</td><td></td><td></td><td>9H</td><td></td>
<td>Corn</td><td></td><td>2U,</td><td>9G</td><td></td><td>10H</td><td></td><td></td><td>9G</td><td></td>
<td>soybeans</td><td></td><td colspan="2">9H</td><td></td><td>9H</td><td></td><td></td><td>9H</td><td></td>
<td>rice</td><td></td><td colspan="2">10E</td><td></td><td>10E</td><td></td><td></td><td>10E</td><td></td>
<td>sorghum</td><td></td><td>2C,</td><td>9G</td><td></td><td>9H</td><td></td><td></td><td>9H</td><td></td>
Nr.371668
Table XII (continued)
<img file="AT371668B_D0046.tif" />
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting bush beans</td><td>9C</td><td>9C</td><td>8C.9G</td>
<td>cotton</td><td>9C</td><td>9C</td><td>9C</td>
<td>Morning Glory</td><td>IOC</td><td>9C</td><td>IOC</td>
<td>barnacles</td><td>9C</td><td>9G</td><td>9C</td>
<td>Ka ssie</td><td>9C</td><td>9C</td><td>IOC</td>
<td>Cyprus grass</td><td>IOC</td><td>2C.8G</td><td>9C</td>
<td>crabgrass</td><td>5C, 8G</td><td>2C.7G</td><td>9C</td>
<td>barnyardgrass</td><td>9C</td><td>9C</td><td>IOC</td>
<td>Wild oats</td><td>9C</td><td>3C.7H</td><td>8C</td>
<td>wheat</td><td>5C.8G</td><td>1C.5H</td><td>8C</td>
<td>Corn</td><td>7U, 9C</td><td>9C</td><td>9C</td>
<td>soybeans</td><td>6C.9G</td><td>9C</td><td>5C, 9G</td>
<td>rice</td><td>9C</td><td>5C.8G</td><td>6C.9G</td>
<td>sorghum</td><td>9C</td><td>9C</td><td>9C</td>
<td>Before sprouting. Morning Glory</td><td>9H</td><td>9G</td><td>9G</td>
<td>barnacles</td><td>9G</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>9G</td><td>9G</td><td>9G</td>
<td>Cyprus grass</td><td>10E</td><td>2C.8G</td><td>10E</td>
<td>crabgrass</td><td>5C, 9G</td><td>2C.9G</td><td>1C, 9G</td>
<td>barnyardgrass</td><td>9H</td><td>2C.9H</td><td>6C.9H</td>
<td>Wild oats</td><td>4C.9G</td><td>2C.8G</td><td>5C.8G</td>
<td>wheat</td><td>9H</td><td>1C.6G</td><td>9H</td>
<td>Corn</td><td>9G</td><td>1U.9G</td><td>9H</td>
<td>soybeans</td><td>9H</td><td>9H</td><td>9H</td>
<td>rice</td><td>10E</td><td>10E</td><td>10E</td>
<td>sorghum</td><td>9H</td><td>9H</td><td>5C.9H</td>
Nr.371668
Table XII (continued)
210 - 212 ° 175 - 179 ° 183 - 184 °
<img file="AT371668B_D0047.tif" />
<img file="AT371668B_D0048.tif" />
<img file="AT371668B_D0049.tif" />
<img file="AT371668B_D0050.tif" />
<img file="AT371668B_D0051.tif" />
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting bush beans</td><td>9C</td><td>9C</td><td>9C</td>
<td>cotton</td><td>9C</td><td>3C, 2H, 4G</td><td>9C</td>
<td>sorghum</td><td>9C</td><td>5C, 9G</td><td>IOC</td>
<td>Corn</td><td>2C, 2H, 5G</td><td>2C, 2H, 7G</td><td>5U.9H</td>
<td>soybeans</td><td>9C</td><td>4C.8G</td><td>IOC</td>
<td>wheat</td><td>9C</td><td>6C.9G</td><td>IOC</td>
<td>Wild oats</td><td>9C</td><td>6C.9G</td><td>IOC</td>
<td>rice</td><td>6C, 9G</td><td>9C</td><td>IOC</td>
<td>barnyardgrass</td><td>9G</td><td>9C</td><td>9C</td>
<td>crabgrass</td><td>2C.8G</td><td>5C, 8G</td><td>9C</td>
<td>Morning Glory</td><td>IOC</td><td>2C, 3H</td><td>IOC</td>
<td>cocklebur</td><td>9C</td><td>4C.9G</td><td>9C</td>
<td>Kassie</td><td>, 6C, 9G</td><td>1C, 3G</td><td>9C</td>
<td>Cyprus grass</td><td>2C, 8G</td><td>4G</td><td>9C</td>
<td>Before sprouting sorghum</td><td>6C.9H</td><td>2C.9G</td><td>7C.9G</td>
<td>Corn</td><td>2C.9G</td><td>2C.7G</td><td>3C.8G</td>
<td>soybeans</td><td>9H</td><td>2C, 2H</td><td>9H</td>
<td>wheat</td><td>2C, 9G</td><td>5G</td><td>9G</td>
<td>Wild oats</td><td>9C</td><td>1C.8H</td><td>6C, 9G</td>
<td>rice</td><td>10E</td><td>10E</td><td>10E</td>
<td>barnyardgrass</td><td>5C.9H</td><td>2C.9H</td><td>9C</td>
<td>crabgrass</td><td>5C, 9H</td><td>1H</td><td>1C.7G</td>
<td>Morning Glory</td><td>9H</td><td>IC</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td>8H</td>
<td>Kassie</td><td>9G</td><td>7G</td><td>5C, 9G</td>
<td>Cyprus grass</td><td>9G</td><td>5G</td><td>10E</td>
- 58 No.371668
Table XII (continued)
181 - 183 °
222 - 226 °
126 - 128 °
<td></td><td>33 E 0 0 oo V<sup>z</sup>\ /</td><td>/ ° \</td><td>z 0 e<sup>m</sup> ec</td>
<td></td><td rowspan="2">O e Z O "E O 2 Q<sup>N</sup>Ο. M \ 1</td><td>1 1 « X IOI ζ ^^, ζ</td><td>c / NC) - <o> gh<sub>3</sub></td>
<td></td><td>CH 1 3 -NHCONH-</td><td>.CH, -NHCONH-</td>
<td></td><td><Q> \</td><td>O o Ο W \ 1 (Ö)</td><td>O o ~</td>
<td></td><td>O 2</td><td></td><td>\ Y /</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>7C, 9G</td><td>2C</td><td>9C</td>
<td>cotton</td><td>6C.9G</td><td>0</td><td>3C, 3H, 7G</td>
<td>sorghum</td><td>IOC</td><td>0</td><td>4U.9G</td>
<td>Corn</td><td>2C.8H</td><td>0</td><td>6C, 9G</td>
<td>soybeans</td><td>9C</td><td>0</td><td>3C, 9G</td>
<td>wheat</td><td>3C, 7G</td><td>0</td><td>3C, 9G</td>
<td>Wild oats</td><td>9C</td><td>0</td><td>6C, 9G</td>
<td>rice</td><td>IOC</td><td>0</td><td>4C, 9G</td>
<td>barnyardgrass</td><td>9C</td><td>0</td><td>9C</td>
<td>crabgrass</td><td>3C, 7G</td><td>0</td><td>2C.8G</td>
<td>Morning Glory</td><td>IOC</td><td>0</td><td>9C</td>
<td>cocklebur</td><td>9C</td><td>0</td><td>9C</td>
<td>Kassie</td><td>5C, 8G</td><td>0</td><td>5C, 8G</td>
<td>Cyprus grass</td><td>7G</td><td>0</td><td>3C.9G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>6C, 9H</td><td>0</td><td>7C.9G</td>
<td>Corn</td><td>2C, 8G</td><td>0</td><td>3U, 9G</td>
<td>soybeans</td><td>9H</td><td>0</td><td>9H</td>
<td>wheat</td><td>8G</td><td>0</td><td>9H</td>
<td>Wild oats</td><td>6C.9G</td><td>0</td><td>3C, 8G</td>
<td>rice</td><td>10E</td><td>0</td><td>10E</td>
<td>barnyardgrass</td><td>6C.9H</td><td>0</td><td>4C, 9H</td>
<td>crabgrass</td><td>2C.5G</td><td>0</td><td>2C, 8G</td>
<td>Morning Glory</td><td>9G</td><td>0</td><td>9G</td>
<td>cocklebur</td><td>8H</td><td>0</td><td>9G</td>
<td>Kassie</td><td>5C, 9G</td><td>0</td><td>1C, 8G</td>
<td>Cyprus grass</td><td>8G</td><td>0</td><td>10E</td>
Nr.371668
Table XII (continued)
183 - 184 °
130 °
<td></td><td>O</td><td></td><td rowspan="2">af af o. o V \ /</td>
<td></td><td>N O «O»</td><td></td>
<td></td><td rowspan="2">□ -Ü o oo \ /<sup>z</sup>v / IOI 2 »2</td><td>X w oo V \ /</td><td>-N Q></td>
<td></td><td>IOI</td><td>1 33</td>
<td></td><td></td><td></td><td>O O</td>
<td></td><td>1</td><td></td><td>ffl 33</td>
<td></td><td>I</td><td>SB</td><td>oz</td>
<td></td><td>33 2</td><td>ö 1 » oz-o</td><td>N oo</td>
<td></td><td>O SB SB O <sup>Z</sup></td><td>O ~ o SB 33 z *</td><td>O co \ _l</td>
<td></td><td>o cT</td><td>oo</td><td></td>
<td></td><td>ow \ _l / <Λ \ \O/</td><td>T (Q></td><td>\ Q / \ 33 2</td>
<td>kg / ha</td><td>0.4</td><td>0.1</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>7C.9G</td><td>8C</td>
<td>cotton</td><td>6C, 9G</td><td>6C, 9G</td><td>6C.8G</td>
<td>sorghum</td><td>1C.9G</td><td>9C</td><td>9C</td>
<td>Corn</td><td>9H</td><td>8U, 9C</td><td>2C, 9G</td>
<td>soybeans</td><td>9C</td><td>5C, 9G</td><td>2C, 9G</td>
<td>wheat</td><td>3A</td><td>6C, 8G</td><td>2C, 8G</td>
<td>Wild oats</td><td>0</td><td>9C</td><td>5C, 8G</td>
<td>rice</td><td>2C.8G</td><td>9C</td><td></td>
<td>barnyardgrass</td><td>3C.8H</td><td>9C</td><td>IOC</td>
<td>crabgrass</td><td>5G</td><td>6C.9G</td><td>8C</td>
<td>Morning Glory</td><td>IOC</td><td>5C, 9G</td><td>9C</td>
<td>cocklebur</td><td>7G</td><td>9C</td><td>9C</td>
<td>Kassie</td><td>5C, 9G</td><td>9C</td><td>7C</td>
<td>Cyprus grass</td><td>1C, 5G</td><td>9C</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>8G</td><td>9H</td><td>9H</td>
<td>Corn</td><td>2C.8G</td><td>3C, 9G</td><td>2C.9G</td>
<td>soybeans</td><td>9H</td><td>8H</td><td>8H</td>
<td>wheat</td><td>0</td><td>2C, 9H</td><td>2C, 9G</td>
<td>Wild oats</td><td>3G</td><td>2C, 8G</td><td>1C.8G</td>
<td>rice</td><td>9H</td><td>10E</td><td>9H</td>
<td>barnyardgrass</td><td>1C.9G</td><td>3C, 9H</td><td>1C.9G</td>
<td>crabgrass</td><td>5G</td><td>8G</td><td>1C, 9G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9H</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>3C, 9G</td><td>2C, 9G</td><td>9G</td>
<td>Cyprus grass</td><td>0</td><td>10E</td><td>10E</td>
Nr.371668
Table XII (continued)
135 ° 183 ° 158 - 160 °
<td></td><td>m<sub>m</sub> s 33 U<sup>ü</sup>V \ / ° 101 33 z O Π ü 33 33 O 2 OO U ω \. 33 2</td><td>33 33 8 8 \ /<sup>2</sup>x / 101 33 2 O 33K ü 2 NN oo o. w \ _l \. 33 2</td><td colspan="2">n! B \ / \ / IOI * y<sup>z</sup>κ j 33 O O 33 2 'N' OO ü M \ _ ( \ Q></td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td colspan="2">0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>5C, 9G</td><td>9C</td><td></td><td>9C</td>
<td>cotton</td><td>3C.6G</td><td>6C, 9G</td><td></td><td>4C, 9G</td>
<td>sorghum</td><td>9C</td><td>9C</td><td></td><td>IOC</td>
<td>Corn</td><td>2C.9G</td><td>8U.9C</td><td></td><td>6C, 9G</td>
<td>soybeans</td><td>2C.9G</td><td>5C.9G</td><td></td><td>5C.9G</td>
<td>wheat</td><td>3C, 8G</td><td>9C</td><td></td><td>5C.9G</td>
<td>Wild oats</td><td>3C.7G</td><td>9C</td><td></td><td>9C</td>
<td>rice</td><td></td><td></td><td></td><td>9C</td>
<td>barnyardgrass</td><td>10G</td><td>IOC</td><td></td><td>IOC</td>
<td>crabgrass</td><td>1C.5G</td><td>9C</td><td></td><td>1C.6G</td>
<td>Morning Glory</td><td>9C</td><td>IOC</td><td></td><td>9C</td>
<td>cocklebur</td><td>1C, 8G</td><td>5C, 8G</td><td></td><td>9C</td>
<td>Kassie</td><td>2C.5G</td><td>3C, 8G</td><td></td><td>9G</td>
<td>Cyprus grass</td><td>1C, 6G</td><td>2C.8G</td><td></td><td>6C.9G</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td>
<td>sorghum</td><td>9G</td><td>1C, 9G</td><td></td><td>10H</td>
<td>Corn</td><td>1C.9G</td><td>1C, 8G</td><td></td><td>9G</td>
<td>soybeans</td><td>1C, 3G</td><td>9H</td><td></td><td>9H</td>
<td>wheat</td><td>9H</td><td>9H</td><td></td><td>9H</td>
<td>Wild oats</td><td>8G</td><td>1C.9G</td><td></td><td>5C.9H</td>
<td>rice</td><td>1QE</td><td>10E</td><td></td><td>10E</td>
<td>barnyardgrass</td><td>1C, 9G</td><td>4C.9H</td><td></td><td>5C.9H</td>
<td>crabgrass</td><td>IC</td><td>1C.9G</td><td></td><td>9G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td></td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td></td><td>9G</td>
<td>Kassie</td><td>7G</td><td>2C, 9G</td><td></td><td>5C, 9G</td>
<td>Cyprus grass</td><td>9G</td><td>10E</td><td></td><td>10E</td>
Nr.371668
Table XII (continued)
178 - 180 °
181 - 183 °
153 - 155 °
Ol \ /<sup>z</sup>y /
101 io s
O
II
e
e
O g
N o
w
<img file="AT371668B_D0052.tif" />
e
O
O
e
N o
Where
O
e
M o
Where/
<td></td><td></td><td></td><td></td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9D.9G</td><td>9C</td><td>3C, 9G, 6Y</td>
<td>cotton</td><td>3Ü.4C.9G</td><td>4C.9G</td><td>2C, 1H</td>
<td>sorghum</td><td>3U.9G</td><td>9G</td><td>9H</td>
<td>Corn</td><td>9C</td><td>2C.9H</td><td>1C, 8H</td>
<td>soybeans</td><td>5C, 9G</td><td>2C.9G</td><td>3H.7G.7X</td>
<td>wheat</td><td>8C</td><td>IC</td><td>IC</td>
<td>Wild oats</td><td>8C</td><td>0</td><td>2G</td>
<td>rice</td><td>9C</td><td>5C, 9G</td><td>1C, 8G</td>
<td>barnyardgrass</td><td>IOC</td><td>3C, 6H</td><td>2C.7H</td>
<td>crabgrass</td><td>5C, 9G</td><td>2C</td><td>2G</td>
<td>Morning Glory</td><td>9C</td><td>9C</td><td>4C.9G</td>
<td>cocklebur</td><td>9C</td><td>9C</td><td>4C.6G</td>
<td>Kassie</td><td>9C</td><td>4C, 6G</td><td>2C</td>
<td>Cyprus grass</td><td>9C</td><td>4G</td><td>0</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>10H</td><td>9G</td><td>9G</td>
<td>Corn</td><td>10E</td><td>9H</td><td>1C, 9G</td>
<td>soybeans</td><td>9H</td><td>2C.8H</td><td>5H</td>
<td>wheat</td><td>9H</td><td>6G</td><td>7G</td>
<td>Wild oats</td><td>2C.8H</td><td>5G</td><td>8G</td>
<td>rice</td><td>10E</td><td>9H</td><td>9H</td>
<td>barnyardgrass</td><td>4C, 9H</td><td>3C, 8H</td><td>2C.6H</td>
<td>crabgrass</td><td>3C.8G</td><td>2G</td><td>1H</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>1C.9G</td>
<td>cocklebur</td><td>9G</td><td>8H</td><td>2C.8G</td>
<td>Kassie</td><td>4C.9G</td><td>5C, 9G</td><td>2C.8G</td>
<td>Cyprus grass</td><td>10E</td><td>4G</td><td>1C.8G</td>
- 62 No.371668
Table XII (continued)
196 - 198 ° 196 - 198 ° 193 - 196 °
<td></td><td>BB OO OO \ / \ / -101</td><td>»B BO \ / \ / ° ©</td><td>ee oo \ / \ / 101 2 2</td>
<td></td><td>B 2 O »O BB ü 2 «Ί N oo \ _ / / P \</td><td>B § "O IT O <sup>2</sup>8th " \ _ / / Q \</td><td>1 B 2 O<sub>m</sub> O BB OZ o "o ο M \ _ / / Q \</td>
<td></td><td>\<sup>u</sup>/ \</td><td>\O/ \</td><td>\<sup>u</sup>/ \</td>
<td></td><td>Ri O</td><td>O</td><td>O</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>9C</td><td>9C</td>
<td>cotton</td><td>4C, 7U, 9G</td><td>5C, 7U, 9G</td><td>5U, 6C, 9G</td>
<td>sorghum</td><td>5U, 9G</td><td>5U, 9G</td><td>IOC</td>
<td>Corn</td><td>5U, 9C</td><td>9C</td><td>IOC</td>
<td>soybeans</td><td>6C.9G</td><td>4C.9G</td><td>IOC</td>
<td>wheat</td><td>4G.9H</td><td>5C, 7G</td><td>IOC</td>
<td>Wild oats</td><td>4C.8G</td><td>5C.8G</td><td>IOC</td>
<td>rice</td><td></td><td></td><td>IOC</td>
<td>barnyardgrass</td><td>9G</td><td>9C</td><td>IOC</td>
<td>crabgrass</td><td>1C.6G</td><td>1C.8G</td><td>5C, 9G</td>
<td>Morning Glory</td><td>IOC</td><td>9C</td><td>9C</td>
<td>cocklebur</td><td>9C</td><td>9C</td><td>9C</td>
<td>Kassie</td><td>9C</td><td>9C</td><td>9C</td>
<td>Cyprus grass</td><td>9C</td><td>9C</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>3C.9H</td><td>9H</td><td>9H</td>
<td>Corn</td><td>2C.9G</td><td>9H</td><td>10H</td>
<td>soybeans</td><td>9H</td><td>9H</td><td>9H</td>
<td>Weizenb</td><td>9H</td><td>10E</td><td>10E</td>
<td>Wild oats</td><td>1C, 9G</td><td>2C.8G</td><td>3C.9H</td>
<td>rice</td><td>10E</td><td>10E</td><td>10E</td>
<td>barnyardgrass</td><td>9H</td><td>5C, 9H</td><td>5C, 9H</td>
<td>crabgrass</td><td>2C.8G</td><td>1C, 9G</td><td>2C, 9G</td>
<td>Morning Glory</td><td>9C</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td></td>
<td>Kassie</td><td>9G</td><td>9G</td><td>9G</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td>10E</td>
- 63 Nr.371668
Table XII (continued)
117 - 130 ° 183 - 184 ° 101 - 112 °
<td></td><td>η B Β 0 0 o V \ ^ / IOI 2 ^^, 2</td><td>n 32 2 o \ /<sup>z</sup>x / IOI 2 ^^ 2</td><td>2 0 B tn o w 2 ^^ 2</td>
<td></td><td>CG</td><td>B</td><td>B</td>
<td></td><td>Z</td><td>2</td><td>2</td>
<td></td><td>O bg</td><td>"0 Β B</td><td>η O 32 32</td>
<td></td><td>0 2</td><td>0 2</td><td>U 2</td>
<td></td><td>* N oo</td><td>northwest oo</td><td></td>
<td></td><td>U CO \ /</td><td>0. w \ _ /</td><td>0 ω \ 1</td>
<td></td><td>(0 /</td><td>(O)</td><td><0> ·</td>
<td></td><td>\ _ /</td><td>\ _ /</td><td>\ _ /</td>
<td>kg / ha</td><td>2</td><td>0.4</td><td>2</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>7C, 9G, 6Y</td><td>6C, 9G, 6Y</td>
<td>cotton</td><td>5C, 9G</td><td>2H, 3C, 8G</td><td>5C, 7G</td>
<td>sorghum</td><td>3C, 9G</td><td>1C.9G</td><td>1C.9G</td>
<td>Corn</td><td>3C, 9G</td><td>8H</td><td>2C, 5G</td>
<td>soybeans</td><td>3C, 8G</td><td>2C.8G</td><td>IC</td>
<td>wheat</td><td>1G.9G</td><td>0</td><td>0</td>
<td>Wild oats</td><td>6C, 9G</td><td>3C</td><td>0</td>
<td>rice</td><td>9C</td><td>3C.9G</td><td></td>
<td>barnyardgrass</td><td>IOC</td><td>3C, 7H</td><td>3C, 5H</td>
<td>crabgrass</td><td>9C</td><td>1C, 5G</td><td>4G</td>
<td>Morning Glory</td><td>IOC</td><td>3C, 9G</td><td>2C.6G</td>
<td>cocklebur</td><td>IOC</td><td>3C, 9G</td><td>5C, 9G</td>
<td>Kassie</td><td>9C</td><td>4C.8H</td><td>2C.4H</td>
<td>Cyprus grass</td><td>1C.9G</td><td>2C, 8G</td><td>6G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>9H</td><td>1C.7G</td><td>2C, 7H</td>
<td>Corn</td><td>9G</td><td>1C.6G</td><td>3C.8G</td>
<td>soybeans</td><td>3H, 6G</td><td>3G</td><td>IG</td>
<td>wheat</td><td>2C, 9G</td><td>0</td><td>IC</td>
<td>Wild oats</td><td>3C, 9G</td><td>0</td><td>IC</td>
<td>rice</td><td>10E</td><td>5G</td><td>10E</td>
<td>barnyardgrass</td><td>9H</td><td>2H</td><td>2C, 4H</td>
<td>crabgrass</td><td>2C, 9G</td><td>2G</td><td>2G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>7G</td>
<td>cocklebur</td><td>9H</td><td>4C, 9H</td><td>9H</td>
<td>Kassie</td><td>8G</td><td>7G</td><td>7G</td>
<td>Cyprus grass</td><td>10E</td><td>5G</td><td>9G</td>
- 64 No. 371668
Table XII (continued)
173 - 175 ° 145 - 150 ° 172 - 173 °
<td></td><td>"N se oo ° \ ^ / ° ioi e Z O η O EE OZ «N oo o W V \O/ \ P { O</td><td>n «B \ x<sup>2</sup>\ / IOI<sup>Z</sup>\ /<sup>Z</sup>e Z O e § oz oo ü w \ _ / \O/ O</td><td>e uv e O (Ί O • \</td><td>m e IOI e Z O O e Z O _ / O> \ R "i O</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td colspan="2">0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>9C</td><td></td><td>9C</td>
<td>cotton</td><td>7C, 9G</td><td>5UE, 6C, 9G</td><td></td><td>5U, 6C, 9G</td>
<td>sorghum</td><td>2C, 8G</td><td>9C</td><td></td><td>IOC</td>
<td>Corn</td><td>IOC</td><td>IOC</td><td></td><td>IOC</td>
<td>soybeans</td><td>IOC</td><td>6C.9G</td><td></td><td>6C.9G</td>
<td>wheat</td><td>6C, 9G</td><td>8C</td><td></td><td>IOC</td>
<td>Wild oats</td><td>9C</td><td>9C</td><td></td><td>9C</td>
<td>rice</td><td></td><td></td><td></td><td></td>
<td>barnyardgrass</td><td>IOC</td><td>IOC</td><td></td><td>IOC</td>
<td>crabgrass</td><td>9C</td><td>IOC</td><td></td><td>9C</td>
<td>Morning Glory</td><td>9C</td><td>9C</td><td></td><td>9C</td>
<td>cocklebur</td><td>9C</td><td>9C</td><td></td><td>9C</td>
<td>Kassie</td><td>9C</td><td>9C</td><td></td><td>9C</td>
<td>Cyprus grass</td><td>IOC</td><td>9C</td><td></td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td>
<td>sorghum</td><td>3U, 9G</td><td>4C, 9G</td><td></td><td>9H</td>
<td>Corn</td><td>9H</td><td>10H</td><td></td><td>9G</td>
<td>soybeans</td><td>9H</td><td>9H</td><td></td><td>9H</td>
<td>wheat</td><td>9H</td><td>10E</td><td></td><td>10E</td>
<td>Wild oats</td><td>2C, 9G</td><td>5C.9G</td><td></td><td>5C.9G</td>
<td>rice</td><td>10E</td><td>10E</td><td></td><td>10E</td>
<td>barnyardgrass</td><td>5C.9H</td><td>6C.9H</td><td></td><td>10H</td>
<td>crabgrass</td><td>5C.9G</td><td>6C.9G</td><td></td><td>6C.9G</td>
<td>Morning Glory</td><td>9G</td><td>9C</td><td></td><td>9H</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td></td><td>9G</td>
<td>Kassie</td><td>9G</td><td>9G</td><td></td><td>9G</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td></td><td>10E</td>
- 65 No.371668
Table XII (continued)
Glass glass 162 - 165 °
<td></td><td colspan="2">e O N O O N SS ο n o o \ /<sup>z</sup>IOI</td><td>s O O CM e 2 pounds IOI</td><td colspan="2">e ü N HM _ 5 E O. ü \ /<sup>z</sup>IOI</td>
<td></td><td>></td><td></td><td>N Λ <sup>1</sup></td><td>N</td><td>CS</td>
<td></td><td>e</td><td>z</td><td>go</td><td rowspan="2">iE 0 CS</td><td>2 Q</td>
<td></td><td>0</td><td>0</td><td rowspan="2">O EE OZ</td><td>0</td>
<td></td><td>O</td><td>CE 2</td><td>O</td><td>z</td>
<td></td><td>O</td><td>O</td><td>"M <M oo</td><td>CM O</td><td>CM O rn</td>
<td></td><td>\</td><td>/</td><td></td><td colspan="2">\ _ /</td>
<td></td><td>/ \</td><td>Q></td><td>LO</td><td>/</td><td></td>
<td>kg / ha</td><td colspan="2">0.4</td><td>0.4</td><td colspan="2">0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td></td><td>9C</td><td>9C</td><td></td><td>9C</td>
<td>cotton</td><td></td><td>6C.8G</td><td>4C.8G</td><td></td><td>4C.8G</td>
<td>sorghum</td><td></td><td>5G</td><td>9H</td><td></td><td>9H</td>
<td>Corn</td><td></td><td>1C.6G</td><td>2C.9H</td><td></td><td>2C.9H</td>
<td>soybeans</td><td></td><td>2C, 9G</td><td>9H</td><td></td><td>9H</td>
<td>wheat</td><td></td><td>0</td><td>0</td><td></td><td>0</td>
<td>Wild oats</td><td></td><td>0</td><td>0</td><td></td><td>0</td>
<td>rice</td><td></td><td>3G</td><td>IC, 9G</td><td></td><td>1C, 9G</td>
<td>barnyardgrass</td><td></td><td>0</td><td>1H</td><td></td><td>1H</td>
<td>crabgrass</td><td></td><td>0</td><td>0</td><td></td><td>0</td>
<td>Morning Glory</td><td></td><td>IOC</td><td>IOC</td><td></td><td>IOC</td>
<td>cocklebur</td><td></td><td>2C, 9G</td><td>9C</td><td></td><td>9C</td>
<td>Kassie</td><td></td><td>2C, 8G</td><td>4C.8G</td><td></td><td>4C, 8G</td>
<td>Cyprus grass</td><td></td><td>1C, 5G</td><td>5G</td><td></td><td>5G</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>sorghum</td><td></td><td>1C.7G</td><td>9G</td><td></td><td>9G</td>
<td>Corn</td><td></td><td>2C.6G</td><td>9G</td><td></td><td>9G</td>
<td>soybeans</td><td></td><td>1C, 2H</td><td>6H</td><td></td><td>9H</td>
<td>wheat</td><td></td><td>0</td><td>0</td><td></td><td>2G</td>
<td>Wild oats</td><td></td><td>0</td><td>4G</td><td></td><td>8G</td>
<td>rice</td><td></td><td>IC</td><td>8H</td><td></td><td>10E</td>
<td>barnyardgrass</td><td></td><td>1H</td><td>3G</td><td></td><td>3C.9H</td>
<td>crabgrass</td><td></td><td>0</td><td>2G</td><td></td><td>1C, 6G</td>
<td>Morning Glory</td><td></td><td>9G</td><td>9G</td><td></td><td>9G</td>
<td>cocklebur</td><td></td><td>9G</td><td>9H</td><td></td><td>9H</td>
<td>Kassie</td><td></td><td>3C, 9G</td><td>4C, 9G</td><td></td><td>5C, 9G</td>
<td>Cyprus grass</td><td></td><td>5G</td><td>5G</td><td></td><td>10E</td>
Nr.371668
Table XII (continued)
112 - 115 °
145 - 147 °
109 - 111 ° o
0, x
CM x
oo
X o
CM
X o
O.
IOI \ /<sup>z</sup>\ /
IOI, 01
X o
ox
CM o
w
X o
sw,
X θ 'o
x
O
X o
Where
0k
X o
X
CM o
ω / q \ \ 0 / \ ^ / w /
<td></td><td></td><td></td><td></td>
<td>kg / ha</td><td>0.4</td><td>2</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9G</td><td>9C</td><td>9C</td>
<td>cotton</td><td>9C</td><td>6C.9G</td><td>9C</td>
<td>sorghum</td><td>9G</td><td>9C</td><td>4U.9G</td>
<td>Corn</td><td>9C</td><td>9C</td><td>9C</td>
<td>soybeans</td><td>5C.9G</td><td>5C, 9G</td><td>9C</td>
<td>wheat</td><td>3G</td><td>2C</td><td>2C, 9G</td>
<td>Wild oats</td><td>1C.8G</td><td>2C.7G</td><td>5C, 9G</td>
<td>rice</td><td>9C</td><td>9C</td><td>9G</td>
<td>barnyardgrass</td><td>3C, 8H</td><td>2C, 5H</td><td>9C</td>
<td>crabgrass</td><td>5G</td><td>5G</td><td>1C.5G</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>cocklebur</td><td>6G</td><td>9C</td><td>9C</td>
<td>Kassie</td><td>2C, 9G</td><td>3C.9G</td><td>9C</td>
<td>Cyprus grass</td><td>4C.8G</td><td>4C, 9G</td><td>9G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>9H</td><td>9H</td><td>9H</td>
<td>Corn</td><td>9G</td><td>9H</td><td>9G</td>
<td>Soy bean</td><td>8H</td><td>9H</td><td>9H</td>
<td>wheat</td><td>2G</td><td>0</td><td>7G</td>
<td>Wild oats</td><td>2G</td><td>1C, 5G</td><td>2C.9G</td>
<td>rice</td><td>9H</td><td>9H</td><td>10E</td>
<td>barnyardgrass</td><td>4H</td><td>2C.7G</td><td>3C.9H</td>
<td>crabgrass</td><td>0</td><td>2G</td><td>8G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td></td>
<td>Kassie</td><td>1G, 9G</td><td>3C, 9G</td><td>5C, 9G</td>
<td>Cyprus grass</td><td>9G</td><td>1C, 9G</td><td>8G</td>
Nr.371668
Table XII (continued)
141 - 143 °
Glass
Glass kg / ha
After sprouting
bush beans
cotton
sorghum
Corn
soybeans
wheat
Wild oats
rice
barnyardgrass
crabgrass
Morning Glory
cocklebur
Kassie
Cyprus grass
Before sprouting
sorghum
Corn
soybeans
wheat
Wild oats
rice
barnyardgrass
crabgrass
Morning Glory
cocklebur
Kassie
Cyprus grass
<img file="AT371668B_D0053.tif" />
/ q \\ z /
0.4
<img file="AT371668B_D0054.tif" />
0.4
<img file="AT371668B_D0055.tif" />
<td>9C</td><td>9C</td><td>9C</td>
<td>6C.9G</td><td>4C.9G</td><td>5C.9G</td>
<td>3C, 9G</td><td>1C.7G</td><td>4G</td>
<td>9H</td><td>9H</td><td>1C, 2H</td>
<td>9C</td><td>2C, 9G</td><td>1H</td>
<td>IC</td><td>0</td><td>0</td>
<td>IC</td><td>0</td><td>0</td>
<td>5C.9G</td><td>1C, 7G</td><td>0</td>
<td>2C, 5H</td><td>2G</td><td>0</td>
<td>4G</td><td>0</td><td>0</td>
<td>IOC</td><td>9C</td><td>2C, 9G</td>
<td>9C</td><td>IG</td><td>3C, 9G</td>
<td>3C.8H</td><td>2C</td><td>2C, 5G</td>
<td>3C, 9G</td><td>0</td><td>0</td>
9G
9H
9H
6G
9H
2C, 7G
2G
9G
9H
SC, 9G
9G
9G
1C.7G
2C
9G
8G
1C, 8G
5G
IC
9G
9G
2C, 9G
Nr.371668
Table XII (continued)
- 75 °
112 - 125 °
150 - 166 ° o
O.
O
M
e
O e
O
O.
O
BO »- * EOO
IOI
e
O o
e
M o
M
IOI
e
O
O
E o
M
e
O
O
e
M o
CO \ o / \ o / kg / ha
0.1
0.1
0.1
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>0</td><td>6G, 6F, 2C</td><td>9G.9D</td>
<td>cotton</td><td>0</td><td>8G</td><td>10G.5D.5C</td>
<td>sorghum</td><td>0</td><td>6G</td><td>9G</td>
<td>Corn</td><td>0</td><td>6G, 3C</td><td>9G</td>
<td>soybeans</td><td>0</td><td>9G, 5H</td><td>9G.5H</td>
<td>wheat</td><td>0</td><td>0</td><td>0</td>
<td>Wild oats</td><td>0</td><td>0</td><td>5G</td>
<td>rice</td><td>0</td><td>8G</td><td>8G, 3C</td>
<td>barnyardgrass</td><td>0</td><td>0</td><td>3G</td>
<td>crabgrass</td><td>4G</td><td>0</td><td>4G</td>
<td>Morning Glory</td><td>0</td><td>9G</td><td>9C</td>
<td>cocklebur</td><td>0</td><td>0</td><td>9C</td>
<td>Kassie</td><td>0</td><td>6G</td><td>10G.5C</td>
<td>Cyprus grass</td><td>0</td><td>0</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>0</td><td>0</td><td>9G</td>
<td>Corn</td><td>0</td><td>0</td><td>9G</td>
<td>soybeans</td><td>0</td><td>0</td><td>9G</td>
<td>wheat</td><td>0</td><td>0</td><td>0</td>
<td>Wild oats</td><td>5E</td><td>0</td><td>8E.7G</td>
<td>rice</td><td>0</td><td></td><td></td>
<td>barnyardgrass</td><td>0</td><td>0</td><td>6G.3G</td>
<td>crabgrass</td><td>0</td><td>0</td><td>0</td>
<td>Morning Glory</td><td>0</td><td>6G</td><td>9G</td>
<td>cocklebur</td><td>10E</td><td>2G</td><td>9G</td>
<td>Kassie</td><td>0</td><td>0</td><td>9G</td>
<td>Cyprus grass</td><td>0</td><td>0</td><td>7G</td>
- 69 Nr.371668
Table XII (continued)
wax
126 - 136 °
125 - 130 °
<img file="AT371668B_D0056.tif" />
0.1
e
O «M o
O
Ε EO-ü O.
\ /<sup>2</sup>\ /
101
101
E §
s
Z
N o
w _ / / r> \ kg / ha
0.1
<td>After sprouting</td><td></td><td></td>
<td>bush beans</td><td>10G.6D</td><td>10G.7D</td>
<td>cotton</td><td>9G.3C.2H</td><td>10G.4C</td>
<td>sorghum</td><td>9G</td><td>9G.5C</td>
<td>Corn</td><td>8G.3C</td><td>9G, 5U</td>
<td>So j ah</td><td>9G, 5H</td><td>19G.5H</td>
<td>wheat</td><td>0</td><td>2G</td>
<td>Wild oats</td><td>0</td><td>7G</td>
<td>rice</td><td>9G</td><td>9G, 5C</td>
<td>barnyardgrass</td><td>0</td><td>7G, 3C</td>
<td>crabgrass</td><td>0</td><td>8G</td>
<td>Morning Glory</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>9C</td><td>2G</td>
<td>Kassie</td><td>8G</td><td>10G.5C</td>
<td>Cyprus grass</td><td>0</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td>
<td>sorghum</td><td>9G</td><td>9G</td>
<td>Corn</td><td>6G</td><td>9G</td>
<td>soybeans</td><td>9G</td><td>9G</td>
<td>wheat</td><td>0</td><td>4G</td>
<td>Wild oats</td><td>6G</td><td>9G</td>
<td>rice</td><td></td><td></td>
<td>barnyardgrass</td><td>3G</td><td>2G, 2 (</td>
<td>crabgrass</td><td>5G</td><td>0</td>
<td>Morning Glory</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>8G</td><td>9G</td>
<td>Cyprus grass</td><td>7G</td><td>8G</td>
so
E ü
e
Z o
O
I u
B
Z α
ow
fr \
0.1
5G
9C
- 70 No.371668
Table XII (continued).
171 - 174 °
138 - 141 °
146 - 151 ° o
O
X o
O
e
O
CM
X o
O,
X o
w
X o
oo
O
N
X o
O
X o
O
X w
O
M
O.
X
O o
X
M o
ω
IOI
X o
O
X
N o
w / <λ \\ o /
<td>kg / ha</td><td>0.1</td><td>2</td><td>0.1</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9G, 5D</td><td>9C</td><td>9G.6F</td>
<td>cotton</td><td>9G, 3C</td><td>9C</td><td>IC</td>
<td>sorghum</td><td>0</td><td>2C.9G</td><td>0</td>
<td>Corn</td><td>0</td><td>lu, 9G</td><td>0</td>
<td>soybeans</td><td>8G, 4H</td><td>4C.9G</td><td>8G, 3H</td>
<td>wheat</td><td>0</td><td>3C, 8H</td><td>0</td>
<td>Wild oats</td><td>0</td><td>8G</td><td>0</td>
<td>rice</td><td>3G</td><td>2C.9G</td><td>0</td>
<td>barnyardgrass</td><td>0</td><td>5C, 9H</td><td>0</td>
<td>crabgrass</td><td>0</td><td>1C, 7G</td><td>0</td>
<td>Morning Glory</td><td>9G, 2C</td><td>IOC</td><td>9G, 3C</td>
<td>cocklebur</td><td>9G</td><td>3G</td><td>8G.3C</td>
<td>Kassie</td><td>8G</td><td>5C.9G</td><td>5G</td>
<td>Cyprus grass</td><td>7G</td><td>9G</td><td>0</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>0</td><td>9H</td><td>0</td>
<td>Corn</td><td>5G</td><td>9G</td><td>0</td>
<td>soybeans</td><td>0</td><td>9H</td><td>0</td>
<td>wheat</td><td>0</td><td>9H</td><td>0</td>
<td>Wild oats</td><td>0</td><td>9H</td><td>0</td>
<td>rice</td><td>0</td><td>10E</td><td></td>
<td>barnyardgrass</td><td>0</td><td>4C, 9H</td><td>0</td>
<td>crabgrass</td><td>0</td><td>2C.8G</td><td>0</td>
<td>Morning Glory</td><td>5G</td><td>9H</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9H</td><td>10E</td>
<td>Kassie</td><td>3G</td><td>9G</td><td>0</td>
<td>Cyprus grass</td><td>0</td><td>10E</td><td>0</td>
Nr.371668
Table XII (continued)
155 - 157 °
151 - 153 °
155 - 157 °
IOI zz
X x
O
N o
0th
O
X z
Where
w
X
II
X
N
X
N o
0
X z
O
X z
N o
w
X i,
X
N
X o
0th
X z
O
X z
cf
M \ o / \ o / \ ^ /
<td></td><td>F-f O</td><td>t-4 Q</td><td>i-1 0</td>
<td>kg / ha</td><td>0.1</td><td>0.1</td><td>0.1</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9G, 3C</td><td>8G, 6F, 3D</td><td>10G.7D</td>
<td>cotton</td><td>10G, 10P, 4C</td><td>10G, 6D, 3C</td><td>10G, 5D, 3C</td>
<td>sorghum</td><td>9G.2C</td><td>9G, 3C</td><td>9G</td>
<td>Corn</td><td>8G.5U</td><td>8G, 3C</td><td>7G</td>
<td>soybeans</td><td>9G, 5H</td><td>9G, 5H</td><td>9G.5H.4C</td>
<td>wheat</td><td>8G</td><td>7G, 2C</td><td>6G</td>
<td>Wild oats</td><td>4G</td><td>4G, 1C</td><td>3G</td>
<td>rice</td><td>9G</td><td>9G</td><td>9G</td>
<td>barnyardgrass</td><td>9C</td><td>9G, 3C</td><td>8G</td>
<td>crabgrass</td><td>5A</td><td>5A</td><td>5A</td>
<td>Morning Glory</td><td>9C</td><td>IOC</td><td>9G.3C</td>
<td>cocklebur</td><td>9C</td><td>IOC</td><td>9G, 3C</td>
<td>Kassie</td><td>9G.6C</td><td>9G, 3C</td><td>8G</td>
<td>Cyprus grass</td><td>8C</td><td>IOC</td><td>6G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>9G, 4C</td><td>9G.2C</td><td>9G</td>
<td>Corn</td><td>9G.4C</td><td>9G</td><td>9G</td>
<td>soybeans</td><td>9G</td><td>9G</td><td>9G</td>
<td>wheat</td><td>6G</td><td>8G</td><td>5G</td>
<td>Wild oats</td><td>6G</td><td>7G</td><td>6G</td>
<td>rice</td><td></td><td></td><td></td>
<td>barnyardgrass</td><td>9G</td><td>9G</td><td>9G, 3C</td>
<td>crabgrass</td><td>0</td><td>5G</td><td>0</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>9G</td><td>9G</td><td>9G</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td>10E</td>
- 72 No. 371668
Table XII (continued).
<td></td><td>127 °</td><td>124 - 128 °</td><td>137 - 140 °</td>
<td></td><td rowspan="3">η n 33 33 OO \ /<sup>2</sup>x / IOI 35 * O 1 II 33 35 2 OO 33 E OZ</td><td>rc W 0 IOI<sup>z</sup>\ /<sup>z</sup>N 0 1</td><td>ρί EB EC 0 "\ / \ / ° io</td>
<td></td><td rowspan="2">az oo MO 33 E O 2</td><td>CJ, |</td>
<td></td><td>33 θ 1 0-0 g</td>
<td></td><td>'Os ^ 00</td><td>oo α w \ _ /</td><td>a ö o 33 1 z O</td>
<td></td><td><0)</td><td>\ O></td><td>0 = 0 ° \ /</td>
<td></td><td>\</td><td>\</td><td>\ O></td>
<td></td><td>O</td><td>O</td><td>\ _ /</td>
<td>kg / ha</td><td>0.1</td><td>0.1</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9G.6F</td><td>9C</td><td>9C</td>
<td>cotton</td><td>10G.4C</td><td>6C, 9G</td><td>5C.9G</td>
<td>sorghum</td><td>6G</td><td>1C.9G</td><td>5U, 9C</td>
<td>Corn</td><td>7G.2G</td><td>3C, 9H</td><td>8U, 9C</td>
<td>soybeans</td><td>9G.5H</td><td>2C, 9G</td><td>5C.9G</td>
<td>wheat</td><td>0</td><td>2C.3G</td><td>2C, 8G</td>
<td>Wild oats</td><td>0</td><td>3C, 4G</td><td>9C</td>
<td>rice</td><td>6G, 2C</td><td>9C</td><td>5C, 9G</td>
<td>barnyardgrass</td><td>7G</td><td>9C</td><td>IOC</td>
<td>crabgrass</td><td>5A</td><td>0</td><td>1C.5G</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td>9C</td>
<td>cocklebur</td><td>IOC</td><td>9C</td><td>9C</td>
<td>Kassie</td><td>9G, 4C</td><td>5C, 9G</td><td>9C</td>
<td>Cyprus grass</td><td>7C</td><td>6C.9G</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>6G</td><td>6G</td><td>9H</td>
<td>Corn</td><td>6G</td><td>1C, 8G</td><td>9H</td>
<td>Soj'abohnen</td><td>9G</td><td>9H</td><td>9H</td>
<td>wheat</td><td>0</td><td>5G</td><td>1C.9G</td>
<td>Wild oats</td><td>5G</td><td>4G</td><td>3C.9G</td>
<td>rice</td><td></td><td></td><td></td>
<td>barnyardgrass</td><td>4G</td><td>1C, 6H</td><td>9C</td>
<td>crabgrass</td><td>0</td><td>0</td><td>2C.8G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>9G</td><td>1C.9G</td><td>9C</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td>10E</td>
- 73 No.371668
Table XII (continued)
174 - 176 ° wax 141 - 144 °
<td></td><td>m B ü m 0 N O 0 N EB H, 0 EC \ A / 101<sup>z</sup>\ /<sup>z</sup>EC Z O n 0 EB EB 0 z «N oo 0 M \ _ / / Z \ 0 /</td><td>b 0 S 0 N O 0 N SB <sup>m</sup>32 O 0 \ /<sup>z</sup>\ / 101 Y * SB SB g 0 o 33 33 0 2 -<sup>N</sup>oo 0 w \ _ / / \\ f 00</td><td>N B 0 II B O SB m 0 33 o 0 101 2 2 SB z O n U ffi » 0 z oo 0 w \ / <0)</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.1</td>
<td>After sprouting bush beans cotton sorghum Corn soybeans wheat Wild oats rice barnyardgrass crabgrass Morning Glory cocklebur Kassie Cyprus grass</td><td>9G.5D 10G.5C 9G 9G.5Ü 9G, 5H 0 3G IOC 4G 0 IOC 9G 9G, 4C 0</td><td>10G.8D 10G.3C 2G 3G.2C 9G.5H 0 0 2G 2C 0 IOC 9C 10G.3C 0</td><td>10G.6D 9C 8G.5L 9G, 5U 9G.5H 0 2G 9G, 4C 7G.5L 0 IOC 8G 9C 8G</td>
<td>Before sprouting sorghum Corn soybeans wheat Wild oats rice barnyardgrass crabgrass Morning Glory cocklebur Kassie Cyprus grass</td><td>9G 8G 9G, 4H 0 5G 3G 0 9G 9G 9G 0</td><td>3G 5G.2C 8G.2H 0 7E 0 IG 0 9G 9G 9G 5G</td><td>9G 9G 9G 4G 9G 8G 0 9G 9G 9G 8G</td>
- 74 No.371668
Table XII (continued)
122 - 125 °
194 - 195 ° o
0th
II
X o
ü
O, {/ \ z
101
O
CM o
M
O
0th
O \ /<sup>Z</sup>\ /
IOI
X
O
X
N o
w / o \ / p> \ \ 0 /
<img file="AT371668B_D0057.tif" />
<td></td><td></td><td></td><td></td>
<td>kg / ha</td><td>0.1</td><td>0.1</td><td>0.1</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9G.3H.3D</td><td>9C</td><td>9C</td>
<td>cotton</td><td>9G.3C</td><td>10G.5C</td><td>9C</td>
<td>sorghum</td><td>8G, 5L</td><td>8G</td><td>IC</td>
<td>Corn</td><td>7G</td><td>9G.5U</td><td>2C</td>
<td>soybeans</td><td>9G, 5H</td><td>9G, 5H</td><td>9C</td>
<td>wheat</td><td>IC</td><td>0</td><td>2G</td>
<td>Wild oats</td><td>IG</td><td>4G</td><td>0</td>
<td>rice</td><td>7G</td><td>9G</td><td></td>
<td>barnyardgrass</td><td>2G</td><td>7G</td><td>6C</td>
<td>crabgrass</td><td>5L</td><td>0</td><td>0</td>
<td>Morning Glory</td><td>IOC</td><td>10C</td><td>10C</td>
<td>cocklebur</td><td>9G.10P</td><td>3G</td><td>IOC</td>
<td>Kassie</td><td>9G</td><td>9C</td><td>9C</td>
<td>Cyprus grass</td><td>4G</td><td>IOC</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>0</td><td>9G</td><td>1C, 9G</td>
<td>Corn</td><td>5G</td><td>9G</td><td>2C.8G</td>
<td>So j ah</td><td>8G</td><td>9G</td><td>9H</td>
<td>wheat</td><td>0</td><td>4G</td><td>5G</td>
<td>Wild oats</td><td>IC</td><td>9G</td><td>1C, 8G</td>
<td>rice</td><td>0</td><td></td><td></td>
<td>barnyardgrass</td><td>0</td><td>9G.10C</td><td>4C.9H</td>
<td>crabgrass</td><td>0</td><td>0</td><td>0</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>9G</td><td>9G</td><td>2H, 7G</td>
<td>Cyprus grass</td><td>5G</td><td>8G</td><td>10E</td>
- 75 No.371668
Table XII (continued)
176 - 178 °
190 - 192 °
137 - 141 °
<img file="AT371668B_D0058.tif" />
IO
X z
O
X z
CM o
Where
0th
Oil
X z
O
X z
ow
/ q \\ O / \ o /
<td></td><td>rh O</td><td>* r<sup>-</sup>1 0</td><td>n ~ f 0</td>
<td>kg / ha</td><td>0.1</td><td>0.1</td><td>0.1</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>7C.9G</td><td>6C, 9G</td>
<td>cotton</td><td>9C</td><td>9C</td><td>7C, 9G</td>
<td>sorghum</td><td>IC</td><td>2U, 9G</td><td>2C, 9G</td>
<td>Corn</td><td>5U</td><td>2U, 9G</td><td>8H</td>
<td>soybeans</td><td>5C</td><td>5C, 9G</td><td>5C, 9G</td>
<td>wheat</td><td>2C</td><td>2C, 9G</td><td>0</td>
<td>Wild oats</td><td>2C</td><td>1C.9G</td><td>5G</td>
<td>rice</td><td>5C</td><td>2C, 9H</td><td>1C, 9G</td>
<td>barnyardgrass</td><td>4C</td><td>3C, 9H</td><td>2C, 8H</td>
<td>crabgrass</td><td>IC</td><td>1C, 2G</td><td>2G</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>cocklebur</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Kassie</td><td>9C</td><td>9C</td><td>5C, 9G</td>
<td>Cyprus grass</td><td>9C</td><td>9C</td><td>5C.9G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>2C.9G</td><td>9H</td><td>1C.8G</td>
<td>Corn</td><td>2U.9G</td><td>9H</td><td>9H</td>
<td>soybeans</td><td>9H</td><td>9H</td><td>9H</td>
<td>wheat</td><td>1C.8G</td><td>7H</td><td>4G</td>
<td>Wild oats</td><td>IC, 9G</td><td>8H</td><td>2C.9G</td>
<td>rice</td><td></td><td></td><td>8G</td>
<td>barnyardgrass</td><td>2C, 9H</td><td>2C.5H</td><td>2C, 7H</td>
<td>crabgrass</td><td>0</td><td>0</td><td>2G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9H</td><td>9H</td>
<td>Kassie</td><td>1C.9G</td><td>2C.8G</td><td>3C, 6G</td>
<td>Cyprus grass</td><td>10E</td><td>9G</td><td>10E</td>
Nr.371668
Table XII (continued)
130 - 133 °
112 - 115 °
115 - 118 ° o
above sea level.
\ ^ /
IOI 2 2 's /
e
O
O
E o
W / ~ \ \ /
O
O.
<sup>z</sup>\ /<sup>2</sup>\ IOI \ /<sup>z</sup>IOI
e
O
O
e
N o
w
O approx
e
O
O
E o * w
/ fs \ \ O / \
<img file="AT371668B_D0059.tif" />
\ o / \ o /
Q
<td>kg / ha</td><td>0.1</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>3C, 7G, 6Y</td><td>3C.8G.6Y</td>
<td>cotton</td><td>9C</td><td>1C.4G</td><td>3C, 9G</td>
<td>sorghum</td><td>5U</td><td>2C, 9H</td><td>1C.8G</td>
<td>Corn</td><td>3C</td><td>0</td><td>2C.8H</td>
<td>soybeans</td><td>5C</td><td>8H</td><td>5C, 9G</td>
<td>wheat</td><td>IC</td><td>0</td><td>0</td>
<td>Wild oats</td><td>IC</td><td>0</td><td>0</td>
<td>rice</td><td>3C</td><td>2G</td><td>1C, 5G</td>
<td>barnyardgrass</td><td>9C</td><td>0</td><td>2G</td>
<td>Finger of grass</td><td>2G</td><td>0</td><td>0</td>
<td>Morning Glory</td><td>IOC</td><td>2C, 8G</td><td>9C</td>
<td>cocklebur</td><td>IOC</td><td>1C.5H</td><td>IOC</td>
<td>Kassie</td><td>9C</td><td>3C</td><td>2C.7G</td>
<td>Cyprus grass</td><td>9C</td><td>0</td><td>9G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>8C, 9H</td><td>3G</td><td>0</td>
<td>Corn</td><td>9G</td><td>5G</td><td>1C, 8G</td>
<td>soybeans</td><td>9H</td><td>0</td><td>9H</td>
<td>wheat</td><td>9G</td><td>0</td><td>0</td>
<td>Wild oats</td><td>10E</td><td>0</td><td>0</td>
<td>rice</td><td>9G</td><td>5G</td><td></td>
<td>barnyardgrass</td><td>3C.9H</td><td>0</td><td>0</td>
<td>crabgrass</td><td>0</td><td>0</td><td>0</td>
<td>Morning Glory</td><td>9G</td><td>0</td><td>4H</td>
<td>cocklebur</td><td>2C, 9H</td><td>4G</td><td>2C.9G</td>
<td>Kassie</td><td>3C, 8H</td><td>0</td><td>0</td>
<td>Cyprus grass</td><td>10E</td><td>0</td><td>0</td>
- 77 No.371668
Table XII (continued)
178 - 181 ° 180 - 183 ° 151 - 153 °
<td></td><td>X x " W IOI V i \ N _Λ O (Q)</td><td>n Sfi 33 Q OO V \ / © / \ 33 f} <sup>Z</sup>\ / 8th<sup>X</sup>ZS<sup>o =</sup>\ z<sup>s</sup>~ \ Q /</td><td>bs V / \ Z 03 OO •O (Q</td><td>w s 8th Oil z SB Z O 8th z N O w / \</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td colspan="2">0.1</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>0</td><td>2C.7G.6Y</td><td>9C</td><td></td>
<td>cotton</td><td>0</td><td>3C.3H.8G</td><td>9C</td><td></td>
<td>sorghum</td><td>2C.6G</td><td>2C, 7G</td><td>10C</td><td></td>
<td>Corn</td><td>3C.6H</td><td>IC, 7G</td><td>9C</td><td></td>
<td>soybeans</td><td>2C, 4H</td><td>2C, 8H</td><td>9C</td><td></td>
<td>wheat</td><td>0</td><td>2G</td><td>IC</td><td></td>
<td>Wild oats</td><td>0</td><td>2C</td><td>IC</td><td></td>
<td>rice</td><td></td><td>1C.8G</td><td>3C</td><td></td>
<td>barnyardgrass</td><td>2C, 3H</td><td>2C, 6H</td><td>10C</td><td></td>
<td>crabgrass</td><td>IC</td><td>0</td><td>3C</td><td></td>
<td>Morning Glory</td><td>IC</td><td>5C.9G</td><td>10C</td><td></td>
<td>cocklebur</td><td>IC</td><td>9C</td><td>9C</td><td></td>
<td>Kassie</td><td>IC</td><td>3C</td><td>2C</td><td></td>
<td>Cyprus grass</td><td>0</td><td>1C, 5G</td><td>7G</td><td></td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td>
<td>sorghum</td><td>0</td><td>2C, 9H</td><td>2U, 9G</td><td></td>
<td>Corn</td><td>0</td><td>2C, 9G</td><td>1C, 8G</td><td></td>
<td>soybeans</td><td>0</td><td>1C, 5G</td><td>8H</td><td></td>
<td>wheat</td><td>0</td><td>2C, 7G</td><td>3G</td><td></td>
<td>Wild oats</td><td>0</td><td>2C.7G</td><td>8H</td><td></td>
<td>rice</td><td>0</td><td>10E</td><td>10E</td><td></td>
<td>barnyardgrass</td><td>0</td><td>1C, 9H</td><td>2C.9H</td><td></td>
<td>crabgrass</td><td>0</td><td>IC, 2H</td><td>0</td><td></td>
<td>Morning Glory</td><td>0</td><td>9G</td><td>9G</td><td></td>
<td>cocklebur</td><td>0</td><td>9H</td><td>9H</td><td></td>
<td>Kassie</td><td>0</td><td>5G</td><td>9G</td><td></td>
<td>Cyprus grass</td><td></td><td>6G</td><td>10E</td><td></td>
- 78 No.371668
Table XII (continued)
153 - 155 ° 142 - 145 ° 115 - 118 °
<td></td><td>Ε E OO oo 'W IOI 2 \ 2</td><td><n «n Ε E CJ O ° \ / \ / IOI</td><td>m CQ 33 ü w IOI \ /<sup>2</sup></td>
<td></td><td rowspan="2">ii i ί V ° e 2 fi ° O CO \ _ /</td><td rowspan="2">11 1 § \ Z o I ü e 2 '«« 4 O o AROUND \ _ /</td><td>e 2 O</td>
<td></td><td>/ \ Ϊ § \ / o üA_ / CO \ _ /</td>
<td></td><td>\ Q / </td><td>\ Q /</td><td>\ Q /</td>
<td>kg / ha</td><td>0.1</td><td>0.1</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>6C, 9G</td><td>9D.9G.6Y</td>
<td>cotton</td><td>9C</td><td>9C</td><td>3C.9G</td>
<td>sorghum</td><td>2C</td><td>4C, 9G</td><td>1C.8G</td>
<td>Corn</td><td>8H</td><td>1C, 8H</td><td>3U, 8G</td>
<td>soybeans</td><td>9C</td><td>9C</td><td>9C</td>
<td>wheat</td><td>0</td><td>2G</td><td>0</td>
<td>Wild oats</td><td>0</td><td>3G</td><td>0</td>
<td>rice</td><td>2C</td><td>3C.7G</td><td>6G</td>
<td>barnyardgrass</td><td>9C</td><td>9C</td><td>IC</td>
<td>crabgrass</td><td>2G</td><td>3G</td><td>IC</td>
<td>Morning Glory</td><td>9C</td><td>9C</td><td>9C</td>
<td>cocklebur</td><td>3C</td><td>5C, 9G</td><td>5C.9G</td>
<td>Kassie</td><td>2C</td><td>3C.8G</td><td>3C, 6G</td>
<td>Cyprus grass</td><td>IC</td><td>1C, 8G</td><td>0</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>9G</td><td>8G</td><td>1C, 8G</td>
<td>Corn</td><td>1C, 7G</td><td>1C.7G</td><td>8G</td>
<td>So j'abohnen</td><td>1H</td><td>3H</td><td>5H</td>
<td>wheat</td><td>2G</td><td>2G</td><td>0</td>
<td>Wild oats</td><td>3G</td><td>3G</td><td>2G</td>
<td>rice</td><td>9H</td><td>9H</td><td>6H</td>
<td>barnyardgrass</td><td>9H</td><td>9H</td><td>1C, 7G</td>
<td>crabgrass</td><td>0</td><td>2G</td><td>2G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9H</td><td>9H</td><td>9G</td>
<td>Kassie</td><td>6G</td><td>8G</td><td>8G</td>
<td>Cyprus grass</td><td>10E</td><td>9G</td><td>5G</td>
Nr.371668
Table XII (continued)
122 - 125 ° 193 - 195 ° 182 - 184 °
<td></td><td>"A</td><td>Etc</td><td></td>
<td></td><td>B 0</td><td>0 0</td><td>0 0</td>
<td></td><td>oo \ / \ /</td><td>oo \ / X /</td><td></td>
<td></td><td>b "IOI</td><td>IOI</td><td>IOI</td>
<td></td><td>\ / · T</td><td>z. z</td><td>|</td>
<td></td><td>/ \ "</td><td>/ \ §</td><td>a "Z BO</td>
<td></td><td>BB 0</td><td></td><td></td>
<td></td><td>0 za</td><td>l<sup>x</sup>'a</td><td>oa</td>
<td></td><td>/ o ~</td><td><sup>2</sup>l N 1 o</td><td>/ * I o</td>
<td></td><td><sup>o =</sup>\ 7</td><td>°<sup>=</sup>\ /</td><td>O-. w \ _ /</td>
<td></td><td>(Q)</td><td>/ Q \ \O/</td><td><Q)</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>3C, 8G, 6Y</td><td>1C, 4G</td>
<td>cotton</td><td>2U, 6D, 9G</td><td>3C, 3H, 9G</td><td>0</td>
<td>sorghum</td><td>1C.9G</td><td>1C, 9G</td><td>0</td>
<td>Corn</td><td>9C</td><td>1C, 9G</td><td>0</td>
<td>So abjhnen</td><td>5C.9G</td><td>2C, 9G</td><td>0</td>
<td>wheat</td><td>0</td><td>1C, 2G</td><td>0</td>
<td>Wild oats</td><td>3G</td><td>1C, 4G</td><td>0</td>
<td>rice</td><td>2C, 7G</td><td>5C, 8G</td><td>4G</td>
<td>barnyardgrass</td><td>2C, 8H</td><td>4C, 9H</td><td>3G</td>
<td>crabgrass</td><td>3G</td><td>2C, 6G</td><td>3G</td>
<td>Morning Glory</td><td>9C</td><td>2C, 9G</td><td>0</td>
<td>cocklebur</td><td>5C, 9G</td><td>2C, 8G</td><td>0</td>
<td>Kassie</td><td>3C, 8G</td><td>2C</td><td>0</td>
<td>Cyprus grass</td><td>2C.8G</td><td>2C, 7G</td><td>0</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>1C.9G</td><td>1C, 9H</td><td>IC</td>
<td>Corn</td><td>9G</td><td>1C, 9G</td><td>3G</td>
<td>soybeans</td><td>2C.8H</td><td>IC</td><td>0</td>
<td>wheat</td><td>IG</td><td>1C, 4G</td><td>0</td>
<td>Wild oats</td><td>6G</td><td>1C.6G</td><td>0</td>
<td>rice</td><td>2C, 8G</td><td>10E</td><td>IC</td>
<td>barnyardgrass</td><td>9H</td><td>1C, 9H</td><td>2C</td>
<td>crabgrass</td><td>IC</td><td>2G</td><td>2G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>0</td>
<td>cocklebur</td><td>9H</td><td>9H</td><td>5G</td>
<td>Kassie</td><td>2C, 9G</td><td>1C.6G</td><td>0</td>
<td>Cyprus grass</td><td>10E</td><td>9G</td><td>0</td>
- 80 No. 371668
Table XIX (continued)
150 - 155 ° 140 - 144 ° 139 - 142 °
<td></td><td>i " 33 Ü</td><td>s' □ s J 3 \ /</td><td>η « BE OO Oy O fol 33 2 O ü b 2 tN O w</td><td>b cg oo j ¥¥ ο-o x 1 ü B \ ° O g / * o = / 8 \ _ / <Q></td><td>a<sup>N</sup>O<sub>=</sub>- II b<sup>n</sup>u \ O ° - \ /</td><td>rt rt ffi ce ooo O<sup>Ζ</sup>· Χ<sup>Ζ</sup>1 33 2 O ü 8th 2 N O w / Q></td>
<td>kg / ha</td><td colspan="3">0.4</td><td>0.4</td><td colspan="2">0.4</td>
<td></td><td colspan="3"></td><td></td><td colspan="2"></td>
<td>After sprouting</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td></td><td></td><td>5C, 9G, 6Y</td><td>5C.9G.6Y</td><td></td><td>9D.9G.6Y</td>
<td>cotton</td><td></td><td></td><td>5C.9G</td><td>5C.9G</td><td></td><td>5C, 9G</td>
<td>sorghum</td><td></td><td></td><td>9G</td><td>9G</td><td></td><td>8G</td>
<td>Corn</td><td></td><td></td><td>2C, 8H</td><td>1C, 9G</td><td></td><td>7G</td>
<td>soybeans</td><td></td><td></td><td>4C.9G</td><td>3H, 7G</td><td></td><td>3H, 6G, 5X</td>
<td>wheat</td><td></td><td></td><td>7G</td><td>3G 8G</td><td></td><td>0</td>
<td>Wild oats</td><td></td><td></td><td>7G</td><td>8G</td><td></td><td>0</td>
<td>rice</td><td></td><td></td><td>5G.8G</td><td>5C, 9G</td><td></td><td>4G</td>
<td>barnyardgrass</td><td></td><td></td><td>5C.9G</td><td>5C, 9G</td><td></td><td>2G</td>
<td>crabgrass</td><td></td><td></td><td>1C.5G</td><td>8G</td><td></td><td>2G</td>
<td>Morning Glory</td><td></td><td></td><td>9G</td><td>10C</td><td></td><td>10C</td>
<td>cocklebur</td><td></td><td></td><td>6C, 9G</td><td>5C, 9G</td><td></td><td>6C.9G</td>
<td>Kassie</td><td></td><td></td><td>2G, 6G</td><td>2C, 5H</td><td></td><td>6C, 9G</td>
<td>Cyprus grass</td><td></td><td></td><td>7G</td><td>8G</td><td></td><td>2G</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td><td></td>
<td>sorghum</td><td></td><td></td><td>9H</td><td>5C.9H</td><td></td><td>9G</td>
<td>Corn</td><td></td><td></td><td>9G</td><td>1C, 9G</td><td></td><td>1C, 7G</td>
<td>So abjhnen</td><td></td><td></td><td>8H</td><td>7H</td><td></td><td>1C.6H</td>
<td>wheat</td><td></td><td></td><td>7G</td><td>1C.7G</td><td></td><td>3G</td>
<td>Wild oats</td><td></td><td></td><td>2C.7G</td><td>1C.7G</td><td></td><td>4G</td>
<td>rice</td><td></td><td></td><td>10E</td><td>10E</td><td></td><td>7G</td>
<td>barnyardgrass</td><td></td><td></td><td>5C, 9H</td><td>9H</td><td></td><td>8G</td>
<td>Finger of grass</td><td></td><td></td><td>1C, 7G</td><td>1C, 6G</td><td></td><td>3G</td>
<td>Morning Glory</td><td></td><td></td><td>8G</td><td>9G</td><td></td><td>9G</td>
<td>cocklebur</td><td></td><td></td><td>9H</td><td>8H</td><td></td><td>9H</td>
<td>Kassie</td><td></td><td></td><td>9G</td><td>8G</td><td></td><td>8G</td>
<td>Cyprus grass</td><td></td><td></td><td>10E</td><td>10E</td><td></td><td>10E</td>
- 81 No.371668
Table XII (continued)
122 - 125 ° 118 - 121 ° 194 - 195 °
<td></td><td>η SS</td><td>tn e</td><td>Ε E</td>
<td></td><td>B3 0</td><td>E 0</td><td>0 0</td>
<td></td><td>0. O</td><td>0 o</td><td>oo</td>
<td></td><td>V \ /</td><td></td><td>\ / \ /</td>
<td></td><td>101</td><td>IO</td><td>101</td>
<td></td><td rowspan="2">ee I o 0 \ / g A g</td><td rowspan="2">Ε Ε I 0 0 \ / g A g</td><td></td>
<td></td><td>V ϊ<sup>1</sup> ü</td>
<td></td><td>Ff E ffi</td><td>Ff E ffi</td><td>E ffi</td>
<td></td><td>0 2 Z</td><td>0 Z 2</td><td>2 z</td>
<td></td><td>o- '8 *</td><td>/ o *</td><td>_ / O</td>
<td></td><td>\ / / \</td><td></td><td><sub>O</sub>_ \ <sub>7</sub></td>
<td></td><td>(Q)</td><td><O)</td><td>\ Q)</td>
<td>kg / ha</td><td>0.1</td><td>0.1</td><td>2</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>9C</td><td>9C</td>
<td>cotton</td><td>6C, 9G</td><td>6C, 9G</td><td>5C, 9G</td>
<td>sorghum</td><td>9H</td><td>9H</td><td>3U, 9G</td>
<td>Corn</td><td>9H</td><td>9H</td><td>7U, 9G</td>
<td>.Sojabohnen</td><td>2C, 9G</td><td>2C, 9G</td><td>9C</td>
<td>wheat</td><td>IG</td><td>IC</td><td>6G, 5X</td>
<td>Wild oats</td><td>IC, 3G</td><td>1C, 3G</td><td>2C, 7G</td>
<td>rice</td><td>IC</td><td>IC</td><td>9C</td>
<td>barnyardgrass</td><td>2C, 3H</td><td>2C, 3H</td><td>9C</td>
<td>crabgrass</td><td>0</td><td>0</td><td>9C</td>
<td>Morning Glory</td><td>9C</td><td>9C</td><td>IOC</td>
<td>cocklebur</td><td>3C.9H</td><td>3C, 9H</td><td>9C</td>
<td>Kassie</td><td>3C, 9G</td><td>3C, 9G</td><td>9C</td>
<td>Cyprus grass</td><td>0</td><td>0</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>2G</td><td>2G</td><td>6C, 9H</td>
<td>Corn</td><td>5G</td><td>5G</td><td>2U, 9G</td>
<td>soybeans</td><td>2C, 5G</td><td>2C, 5G</td><td>9H</td>
<td>wheat</td><td>0</td><td>0</td><td>9G</td>
<td>Wild oats</td><td>0</td><td>0</td><td>2C, 9G</td>
<td>rice</td><td>0</td><td>0</td><td>10E</td>
<td>barnyardgrass</td><td>2G</td><td>2G</td><td>10H</td>
<td>crabgrass</td><td>0</td><td>0</td><td>3G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td>9H</td>
<td>Kassie</td><td>5G</td><td>5G</td><td>9G</td>
<td>Cyprus grass</td><td>9G</td><td>9G</td><td>10E</td>
Nr.371668
Table XII (continued).
199 - 200 ° 147 - 150 ° 164 - 166 °
<img file="AT371668B_D0060.tif" />
<td>kg / ha</td><td>2</td><td>2</td><td>0.4</td>
<td>After sprouting bush beans</td><td>3C, 9G, 6Y</td><td>10D.9G</td><td>9D, 9G, 6Y</td>
<td>cotton</td><td>2C, 2H</td><td>9C</td><td>4C.9G</td>
<td>sorghum</td><td>1C.7H</td><td>3U, 9G</td><td>2C.9G</td>
<td>Corn</td><td>2G</td><td>9U, 9G</td><td>2C, 9H</td>
<td>soybeans</td><td>2C.5G</td><td>9C</td><td>3C, 9G</td>
<td>wheat</td><td>0</td><td>3C, 8G</td><td>2C, 8H</td>
<td>Wild oats</td><td>0</td><td>2C, 8G</td><td>2G.9H</td>
<td>rice</td><td>2C, 5G</td><td>6C, 8G</td><td>5C, 8G</td>
<td>barnyardgrass</td><td>3G.7H</td><td>9C</td><td>5C, 9H</td>
<td>crabgrass</td><td>1C.3G</td><td>9C</td><td>5G</td>
<td>Morning Glory</td><td>3C.8G</td><td>IOC</td><td>9C</td>
<td>cocklebur</td><td>3C.6G</td><td>IOC</td><td>5C, 9H</td>
<td>Kassie</td><td>IC</td><td>9C</td><td>6C.9G</td>
<td>Cyprus grass</td><td>2G</td><td>5C.9G</td><td>9G</td>
<td>Before sprouting sorghum</td><td>2C, 6H</td><td>9H</td><td>2C, 9H</td>
<td>Corn</td><td>7H</td><td>2C, 9G</td><td>9G</td>
<td>soybeans</td><td>1C.3H</td><td>9H</td><td>9H</td>
<td>wheat</td><td>0</td><td>9G</td><td>IG</td>
<td>Wild oats</td><td>0</td><td>3C, 9G</td><td>1C, 6G</td>
<td>rice</td><td>2C, 5H</td><td>10E</td><td>9H</td>
<td>barnyardgrass</td><td>2C, 9H</td><td>9H</td><td>2C, 8H</td>
<td>crabgrass</td><td>0</td><td>7G</td><td>2G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9G</td>
<td>cocklebur</td><td></td><td>9H</td><td>9H</td>
<td>Kassie</td><td>2C, 3H</td><td>9G</td><td>2C.8G</td>
<td>Cyprus grass</td><td>0</td><td>10E</td><td>7G</td>
Nr.371668
Table XII (continued)
184 - 186 °
122 - 127 °
184 - 185 °
IOI ·
<td></td><td></td><td>B Z</td>
<td>B</td><td>m</td><td>O</td>
<td>0</td><td>B</td><td>0</td>
<td>2 - /</td><td>• 0</td><td>B 2 O* M</td>
<img file="AT371668B_D0061.tif" />
\ ^ /
<img file="AT371668B_D0062.tif" />
PJ io s
0s
2-E
B
O
B
Z
N
O ω
o =
B
O
E θ
m \ _ / \ O /
<td>kg / ha</td><td>0.4</td><td>0.1</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>9C</td><td>8D, 9G, 6Y</td>
<td>cotton</td><td>9C</td><td>3C, 8G</td><td>6C, 9G</td>
<td>sorghum</td><td>9C</td><td>2G, 9G</td><td>9C</td>
<td>Corn</td><td>7U.9G</td><td>3C.9H</td><td>3U, 9G</td>
<td>soybeans</td><td>6C, 9G</td><td>3C, 9G</td><td>9C</td>
<td>wheat</td><td>5C.9G</td><td>0</td><td>1C, 4G</td>
<td>Wild oats</td><td>6C.9G</td><td>0</td><td>2C.7G</td>
<td>rice</td><td>9G</td><td>3C, 5G</td><td>IOC</td>
<td>barnyardgrass</td><td>IOC</td><td>3C, 9G</td><td>IOC</td>
<td>crabgrass</td><td>9C</td><td>2C, 8G</td><td>2C, 8G</td>
<td>Morning Glory</td><td>9C</td><td>5C.9G</td><td>IOC</td>
<td>cocklebur</td><td>9C</td><td>IC</td><td>IOC</td>
<td>Kassie</td><td>9C</td><td>2C</td><td>9C</td>
<td>Cyprus grass</td><td>IOC</td><td>2C, 9G</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>10H</td><td>2C, 5G</td><td>6C, 9H</td>
<td>Corn</td><td>9G</td><td>1C, 9G</td><td>3U, 9G</td>
<td>soybeans</td><td>9H</td><td>IC</td><td>9H</td>
<td>wheat</td><td>10E</td><td>0</td><td>5G</td>
<td>Wild oats</td><td>5C, 9H</td><td>0</td><td>6G</td>
<td>rice</td><td>10E</td><td>2C, 5G</td><td>9H</td>
<td>barnyardgrass</td><td>9H</td><td>1C, 2G</td><td>3C, 9H</td>
<td>crabgrass</td><td>2C, 9G</td><td>3G</td><td>3C, 5G</td>
<td>Morning Glory</td><td>9G</td><td>SG</td><td>9G</td>
<td>cocklebur</td><td>9H</td><td></td><td>9G</td>
<td>Kassie</td><td>1C.9G</td><td>1C.3H</td><td>3C, 9G</td>
<td>Cyprus grass</td><td>10E</td><td>0</td><td>10E</td>
Nr.371668
Table XII (continued).
188 - 190 °
181 - 183 °
158 - 161 ° kOi
B
O
O
B
N o
w / '\
/ bo<sup>2</sup>x /
IO!
B
O
O
B
O w
\ /<sup>z</sup>x /
LOi / \ V / ./
B
O ü
B
Z
N o
w
<img file="AT371668B_D0063.tif" />
\ o / / <λ \ \ o /
<td></td><td></td><td></td><td></td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9D, 9G, 6Y</td><td>0</td><td>10D, 9G, 6Y</td>
<td>cotton</td><td>6C, 9G</td><td>0</td><td>5C, 9G</td>
<td>sorghum</td><td>IOC</td><td>0</td><td>IOC</td>
<td>Corn</td><td>5C, 9H</td><td>0</td><td>7U, 9C</td>
<td>soybeans</td><td>9C</td><td>0</td><td>9C</td>
<td>wheat</td><td>6C, 9G</td><td>0</td><td>5C, 9G</td>
<td>Wild oats</td><td>5C, 9G</td><td>0</td><td>4C, 9G</td>
<td>rice</td><td>IOC</td><td>0</td><td>9C</td>
<td>barnyardgrass</td><td>IOC</td><td>0</td><td>IOC</td>
<td>crabgrass</td><td>9C</td><td>0</td><td>4C, 9G</td>
<td>Morning Glory</td><td>IOC</td><td>0</td><td>IOC</td>
<td>cocklebur</td><td>IOC</td><td>0</td><td>9C</td>
<td>Kassie</td><td>9C</td><td>0</td><td>3C.8G</td>
<td>Cyprus grass</td><td>8C</td><td>0</td><td>1C, 9G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>7C.9H</td><td>0</td><td>10H</td>
<td>Corn</td><td>9G</td><td>0</td><td>10E</td>
<td>soybeans</td><td>9H</td><td>0</td><td>8H</td>
<td>wheat</td><td>1C, 9G</td><td>0</td><td>1C, 9G</td>
<td>Wild oats</td><td>3C, 9G</td><td>0</td><td>3C, 9G</td>
<td>rice</td><td>10E</td><td>0</td><td>10E</td>
<td>barnyardgrass</td><td>5C.9H</td><td>3C</td><td>4C, 9H</td>
<td>crabgrass</td><td>2C</td><td>2G</td><td>IC</td>
<td>Morning Glory</td><td>9G</td><td>0</td><td>9G</td>
<td>cocklebur</td><td>9G</td><td>0</td><td></td>
<td>Kassie</td><td>2C.9G</td><td>0</td><td>9G</td>
<td>Cyprus grass</td><td>10E</td><td>5G</td><td>10E</td>
Nr.371668
Table XII (continued)
136.5 - 144 ° 144 - 149 °
<td></td><td>XX oooo IOI X / | 1</td><td>" X</td><td>x O Ίοι 2 2</td>
<td></td><td>NI</td><td></td><td>e</td>
<td></td><td>X®</td><td></td><td>2</td>
<td></td><td>"O 2</td><td></td><td>O</td>
<td></td><td>X II O Ö-o Ü</td><td>m X</td><td>O X</td>
<td></td><td>IX</td><td>O</td><td>2</td>
<td></td><td>2</td><td>N</td><td>w</td>
<td></td><td>EN</td><td>O</td><td>O</td>
<td></td><td>O o</td><td>above sea level.</td><td>co</td>
<td></td><td>Ο M I /</td><td>\</td><td>_ /</td>
<td></td><td></td><td>(Q</td><td></td>
<td></td><td>\ / <O></td><td></td><td>V \.</td>
<td></td><td></td><td></td><td>2</td>
<td>kg / ha</td><td>0.1</td><td colspan="2">0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>9C</td><td></td><td>10C, 9G, 6Y</td>
<td>cotton</td><td>3C, 4H, 9G</td><td></td><td>6C, 9G</td>
<td>sorghum</td><td>5G</td><td></td><td>9C</td>
<td>Corn</td><td>6G</td><td></td><td>7UE, 9G</td>
<td>soybeans</td><td>1C, 2H</td><td></td><td>6C, 9G</td>
<td>wheat</td><td>0</td><td></td><td>3C, 8G</td>
<td>Wild oats</td><td>0</td><td></td><td>9C</td>
<td>rice</td><td>1C, 5G</td><td></td><td>6C, 9G</td>
<td>barnyardgrass</td><td>2G</td><td></td><td>9C</td>
<td>crabgrass</td><td>2G</td><td></td><td>9C</td>
<td>Morning Glory</td><td>IOC</td><td></td><td>IOC</td>
<td>cocklebur</td><td>3C, 9G</td><td></td><td>5C.9G</td>
<td>Kassie</td><td>6C, 9G</td><td></td><td>2C, 3G</td>
<td>Cyprus grass</td><td>5G</td><td></td><td>8G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>1C, 7G</td><td></td><td>5C, 9H</td>
<td>Corn</td><td>1C.6G</td><td></td><td>3C.9G</td>
<td>soybeans</td><td>1H</td><td></td><td>8H</td>
<td>wheat</td><td>1C, 4G</td><td></td><td>2C, 9H</td>
<td>Wild oats</td><td>1C, 5G</td><td></td><td>4C, 9G</td>
<td>rice</td><td>5H</td><td></td><td>10E</td>
<td>barnyardgrass</td><td>3C, 4G</td><td></td><td>5C.9H</td>
<td>crabgrass</td><td>0</td><td></td><td>2C, 9G</td>
<td>Morning Glory</td><td>9G</td><td></td><td>9G</td>
<td>cocklebur</td><td>9H</td><td></td><td>9H</td>
<td>Kassie</td><td>9G</td><td></td><td>1C.9G</td>
<td>Cyprus grass</td><td>9G</td><td></td><td>10E</td>
- 86 No.371668
Table XII (continued).
166 - 168 ° 152 - 154 ° 184 - 187 °
<td></td><td></td><td></td><td>«Π X</td><td></td><td></td>
<td></td><td></td><td>X</td><td>X ü</td><td>Λ</td><td>X</td>
<td></td><td>X</td><td>ü</td><td>oo</td><td>X</td><td>0</td>
<td></td><td colspan="2">ο. O</td><td>\ /<sup>2</sup>\ /</td><td></td><td>Y</td>
<td></td><td>pi</td><td></td><td>"IOI 0 0 1</td><td>IO.</td><td></td>
<td></td><td>x "|</td><td></td><td>\ / Y</td><td><sup>z</sup>\ / ·</td><td></td>
<td></td><td>0 N m 1</td><td></td><td>X 0 1</td><td>/ ° \ 1</td><td></td>
<td></td><td rowspan="2">XXX 0 0 z \ / g</td><td></td><td>\ 5</td><td>1 1 ®</td><td></td>
<td></td><td></td><td>\ o X CJ</td><td>O LJ ü</td><td></td>
<td></td><td>ZX</td><td></td><td>ZX</td><td>Y / x</td><td></td>
<td></td><td>1 <sup>z</sup></td><td></td><td>/ *</td><td>2 z</td><td></td>
<td></td><td>cf</td><td></td><td>/ o</td><td>/ °</td><td></td>
<td></td><td>° = \ _ /</td><td></td><td>O = (co \ _ /</td><td>O = (co \ _ /</td><td></td>
<td></td><td><Q></td><td></td><td><Q></td><td>(Q)</td><td></td>
<td>kg / ha</td><td colspan="2">0.4</td><td>0.4</td><td colspan="2">0.4</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>7C, 9G, 6Y</td><td></td><td>8C, 9G, 6Y</td><td>8C, 9G, 6Y</td><td></td>
<td>cotton</td><td>9C.9G</td><td></td><td>7C, 9G</td><td>9C, 9G</td><td></td>
<td>sorghum</td><td>5C, 9G</td><td></td><td>2C.8H</td><td>2C, 8G</td><td></td>
<td>Corn</td><td>8U, 9C</td><td></td><td>5UE, 9C</td><td>5Ü.8G</td><td></td>
<td>soybeans</td><td>BC.9G</td><td></td><td>6C, 9G</td><td>6C.9G</td><td></td>
<td>wheat</td><td>0</td><td></td><td>0</td><td>0</td><td></td>
<td>Wild oats</td><td>2C.8G</td><td></td><td>0</td><td>1C, 8G</td><td></td>
<td>rice</td><td>5C, 8G</td><td></td><td>2G, 8G</td><td>3C, 9G</td><td></td>
<td>barnyardgrass</td><td>6C, 9H</td><td></td><td>1C.3H</td><td>7C, 9H</td><td></td>
<td>crabgrass</td><td>6C, 9G</td><td></td><td>1C, 4G</td><td>1G, 5G</td><td></td>
<td>Morning Glory</td><td>IOC</td><td></td><td>IOC</td><td>9C</td><td></td>
<td>cocklebur</td><td>9C</td><td></td><td>9C</td><td>2C, 8G</td><td></td>
<td>Kassie</td><td>9C</td><td></td><td>9C</td><td>9G</td><td></td>
<td>Cyprus grass</td><td>2C.8G</td><td></td><td>1C, 3G</td><td>0</td><td></td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td>sorghum</td><td>6C.9H</td><td></td><td>2C, 9H</td><td>1C, 9G</td><td></td>
<td>Corn</td><td>5C, 9G</td><td></td><td>2C, 9G</td><td>2C, 9G</td><td></td>
<td>soybeans</td><td>9H</td><td></td><td>9H</td><td>3C, 8H</td><td></td>
<td>wheat</td><td>3G</td><td></td><td>0</td><td>0</td><td></td>
<td>Wild oats</td><td>4C, 9G</td><td></td><td>1C.5G</td><td>1C.8G</td><td></td>
<td>rice</td><td>10E</td><td></td><td>10E</td><td>2C.8H</td><td></td>
<td>barnyardgrass</td><td>3C.9H</td><td></td><td>2C.8G</td><td>2C.8G</td><td></td>
<td>crabgrass</td><td>2C, 7G</td><td></td><td>2C, 6G</td><td>IC</td><td></td>
<td>Morning Glory</td><td>9G</td><td></td><td>9G</td><td>2C, 9G</td><td></td>
<td>cocklebur</td><td>9H</td><td></td><td>9H</td><td>9H</td><td></td>
<td>Kassie</td><td>3C, 9G</td><td></td><td>4G.9G</td><td>2C.9G</td><td></td>
<td>Cyprus grass</td><td>1C.8G</td><td></td><td>5G</td><td>0</td><td></td>
- 87 No.371668
Table XII (continued)
158 - 159 ° 182 - 186 ° 215 °
<td></td><td>«B oo \ /<sup>z</sup>Ioi \ i \ / § ? <sup>z </sup>/ <Q></td><td>s oe oo \ /<sup>2</sup>IOI B Z O <»CJ) »B ü Z NM oo ü w \ / / Q \ \ P / \. e Z</td><td>irt n EE U ü oo \ /<sup>z</sup>\ / IOI <sup>z</sup>\ /<sup>z</sup>«> 03 Eat Ο 1 ß O 33 v! l * °<sup>=</sup>\ / (Q)</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td><td></td>
<td>bush beans</td><td>7C.9G.6Y</td><td>7C, 9G, 6Y</td><td>7C.9G.6Y</td>
<td>cotton</td><td>8C.9G</td><td>7C.9G</td><td>9C.9G</td>
<td>sorghum</td><td>9C</td><td>9C</td><td>IOC</td>
<td>Corn</td><td>IOC</td><td>5U, 9C</td><td>4U.9H</td>
<td>Soy bean</td><td>5C.9G</td><td>9C</td><td>9C</td>
<td>wheat</td><td>1C, 7G</td><td>9C</td><td>5C.9G</td>
<td>Wild oats</td><td>3C.8G</td><td>9C</td><td>9C</td>
<td>rice</td><td>6C, 9G</td><td>5C, 9G</td><td>6C, 9G</td>
<td>barnyardgrass</td><td>9C</td><td>IOC</td><td>9C</td>
<td>crabgrass</td><td>6C, 9G</td><td>IOC</td><td>2C.8G</td>
<td>Morning Glory</td><td>IOC</td><td>9C</td><td>9C</td>
<td>cocklebur</td><td>9C</td><td>5C.9G</td><td>9C</td>
<td>Kassie</td><td>3C.8G</td><td>6C, 9G</td><td>9C</td>
<td>Cyprus grass</td><td>1C.7G</td><td>1C, 9G</td><td>3C, 8G</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>sorghum</td><td>6C.9H</td><td>5C.9H</td><td>8C.9G</td>
<td>Corn</td><td>4C.9G</td><td>1C.7G</td><td>1U.9G</td>
<td>soybeans</td><td>2C.7H</td><td>9H</td><td>9H</td>
<td>wheat</td><td>3C.9G</td><td>1C, 9G</td><td>1C, 9G</td>
<td>Wild oats</td><td>3C.9H</td><td>4C, 9G</td><td>3C.9H</td>
<td>rice</td><td>10E</td><td>10E</td><td>10E</td>
<td>barnyardgrass</td><td>5C, 9H</td><td>4C, 9H</td><td>8C, 9H</td>
<td>crabgrass</td><td>2C, 8G</td><td>1C, 8G</td><td>3C, 8G</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>9C</td>
<td>cocklebur</td><td>9H</td><td>9H</td><td>9H</td>
<td>Kassie</td><td>5C.9G</td><td>9G</td><td>3C, 9G</td>
<td>Cyprus grass</td><td>2C, 9G</td><td>1C.9G</td><td>10E</td>
- 88 No. 371668
Table XII (continued).
Rubber glass
<td></td><td colspan="2">M e O II e O N «B</td><td colspan="2">e O III O N E »</td>
<td></td><td colspan="2">SO oo Y<sup>z</sup>\ / • IOI e O ll</td><td>CM e O</td><td>8 p \ /<sup>z</sup>\ / 10!</td>
<td></td><td>Ο B</td><td></td><td>b<sup>n</sup></td><td>X</td>
<td></td><td>E Ο O ü</td><td></td><td>O O</td><td rowspan="2">O O e Z N</td>
<td></td><td>1 <sup>2</sup>CM</td><td></td><td>I</td>
<td></td><td>- - ι O O =. 03 \ A /</td><td></td><td>"\ (</td><td>O ω _ / o></td>
<td>kg / ha</td><td colspan="2">0.1</td><td colspan="2">0.1</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>2C, 2H</td><td></td><td></td><td>9G, 3H, 5D</td>
<td>cotton</td><td>2C.2H</td><td></td><td></td><td>9G, 3C</td>
<td>sorghum</td><td>IC</td><td></td><td></td><td>5G</td>
<td>Corn</td><td>1C.3H</td><td></td><td></td><td>6G</td>
<td>soybeans</td><td>1C.5G</td><td></td><td></td><td>9G.3H</td>
<td>wheat</td><td>0</td><td></td><td></td><td>0</td>
<td>Wild oats</td><td>0</td><td></td><td></td><td>0</td>
<td>rice</td><td>4G</td><td></td><td></td><td>5G</td>
<td>barnyardgrass</td><td>0</td><td></td><td></td><td>0</td>
<td>crabgrass</td><td>0</td><td></td><td></td><td>0</td>
<td>Morning Glory</td><td>IC</td><td></td><td></td><td>IOC</td>
<td>cocklebur</td><td>IC</td><td></td><td></td><td>IOC</td>
<td>Kassie</td><td>0</td><td></td><td></td><td>8G</td>
<td>Cyprus grass</td><td>1C.4G</td><td></td><td></td><td>IOC</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td>
<td>sorghum</td><td>2G</td><td></td><td></td><td>8G</td>
<td>Corn</td><td>1C.7G</td><td></td><td></td><td>8G</td>
<td>soybeans</td><td>2C</td><td></td><td></td><td>5G</td>
<td>wheat</td><td>2G</td><td></td><td></td><td>0</td>
<td>Wild oats</td><td>IC</td><td></td><td></td><td>SG</td>
<td>rice</td><td>3C.7H</td><td></td><td></td><td></td>
<td>barnyardgrass</td><td>3C.8H</td><td></td><td></td><td>0</td>
<td>crabgrass</td><td>0</td><td></td><td></td><td>0</td>
<td>Morning Glory</td><td>4G</td><td></td><td></td><td>9G</td>
<td>cocklebur</td><td>9H</td><td></td><td></td><td>9G</td>
<td>Kassie</td><td>4G</td><td></td><td></td><td>9G</td>
<td>Cyprus grass</td><td>5G</td><td></td><td></td><td>8G</td>
Nr.371668
Table XII (continued)
148 - 153 ° wax wax
<td></td><td>WP) S CB 8 8 IOI V- 1 mz - oo tn fj 33 ä OZ WN OO Q, " \ _ / / P> \ \O/</td><td>N rt 33 U 33 * G \ / * \ / 'IOI o 1 BB 3 33 Z OO Λ ° Ο 33 / a = l 8 Y_ / <Q)</td><td>N " 33 ü CB ü 1 O °<sup>J</sup>\ / \</td><td>33 ü "n rj 33 X \ Z V<sup>Z</sup>x / v 33 Z O O 33 Z N O w _ / Q /</td>
<td>kg / ha</td><td>0.4</td><td>0.1</td><td colspan="2">0.1</td>
<td>After sprouting</td><td></td><td></td><td></td><td></td>
<td>bush beans</td><td>5S, 9G, 6Y</td><td>10G.7C</td><td></td><td>1H.6Y.5G</td>
<td>cotton</td><td>7C, 9G</td><td>10G.5C</td><td></td><td>0.0</td>
<td>sorghum</td><td>3C, 9G</td><td>7G</td><td></td><td>0.0</td>
<td>Corn</td><td>9C</td><td>7G</td><td></td><td>3G, 0</td>
<td>soybeans</td><td>6C, 9G</td><td>9G, 5H</td><td></td><td>2H, 7G, 5X</td>
<td>wheat</td><td>3C.9G</td><td>0</td><td></td><td>0.0</td>
<td>Wild oats</td><td>6C, 9H</td><td>0</td><td></td><td>0.0</td>
<td>rice</td><td></td><td>2G</td><td></td><td>0</td>
<td>barnyardgrass</td><td>IOC</td><td>0</td><td></td><td>0.0</td>
<td>crabgrass</td><td>2C, 8G</td><td>0</td><td></td><td>0.0</td>
<td>Morning Glory</td><td>9C</td><td>IOC</td><td></td><td>5G, 4G</td>
<td>cocklebur</td><td>IOC</td><td>9C</td><td></td><td>0.3G</td>
<td>Kassie</td><td>9C</td><td>10G.10P</td><td></td><td>0.0</td>
<td>Cyprus grass</td><td>6C.9G</td><td>9G</td><td></td><td>0.0</td>
<td>Before sprouting</td><td></td><td></td><td></td><td></td>
<td>sorghum</td><td>1C, 9G</td><td>9G.3H</td><td></td><td>0.0</td>
<td>Corn</td><td>1C, 9G</td><td>6G</td><td></td><td>2G, 0</td>
<td>soybeans</td><td>6H</td><td>9G</td><td></td><td>0.0</td>
<td>wheat</td><td>1C, 9H</td><td>0</td><td></td><td>0.0</td>
<td>Wild oats</td><td>1C, 9H</td><td>5G</td><td></td><td>0.0</td>
<td>rice</td><td>10E</td><td>0</td><td></td><td>0</td>
<td>barnyardgrass</td><td>2C, SH</td><td>0</td><td></td><td>0.0</td>
<td>crabgrass</td><td>IC, SG</td><td>0</td><td></td><td>0.0</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td></td><td>0.0</td>
<td>cocklebur</td><td>9G</td><td>9G</td><td></td><td>0</td>
<td>Kassie</td><td>3C</td><td>9G</td><td></td><td>0.0</td>
<td>Cyprus grass</td><td>9G</td><td>8G</td><td></td><td>0.5G</td>
Nr.371668
Table XII (continued).
105 - 110 °
- 90 °
X z
oo
X z
N o
w
<img file="AT371668B_D0064.tif" />
<img file="AT371668B_D0065.tif" />
X
-o \ O /
<td></td><td>O 2</td><td>O z</td>
<td>kg / ha</td><td>0.4</td><td>0.4</td>
<td>After sprouting</td><td></td><td></td>
<td>bush beans</td><td>9C</td><td>9C</td>
<td>cotton</td><td>9C</td><td>6C, 9G</td>
<td>sorghum</td><td>10C</td><td>10C</td>
<td>Corn</td><td>9C</td><td>9C</td>
<td>soybeans</td><td>9C</td><td>9C</td>
<td>wheat</td><td>10C</td><td>10C</td>
<td>Wild oats</td><td>10C</td><td>10C</td>
<td>rice</td><td>10C</td><td>9C</td>
<td>barnyardgrass</td><td>10C</td><td>10C</td>
<td>crabgrass</td><td>10C</td><td>9C</td>
<td>Morning Glory</td><td>9C</td><td>10C</td>
<td>cocklebur</td><td>9C</td><td>10C</td>
<td>Kassie</td><td>9C</td><td>9C</td>
<td>Cyprus grass</td><td>5C.9G</td><td>9C</td>
<td>Before sprouting</td><td></td><td></td>
<td>sorghum</td><td>10H</td><td>5C, 9H</td>
<td>Corn</td><td>3C, 9H</td><td>3U, 9G</td>
<td>soybeans</td><td>9H</td><td>9H</td>
<td>wheat</td><td>3C, 9H</td><td>9H</td>
<td>Wild oats</td><td>5C, 9G</td><td>6C.9G</td>
<td>rice</td><td>10E</td><td>10E</td>
<td>barnyardgrass</td><td>5C.9H</td><td>6C, 9H</td>
<td>crabgrass</td><td>3C.9H</td><td>5C, 9H</td>
<td>Morning Glory</td><td>9H</td><td>9H</td>
<td>cocklebur</td><td>9G</td><td>9G</td>
<td>Kassie</td><td>8G</td><td>6C.9G</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td>
Nr.371668
Table XII (continued)
120 - 125 ° rubber 116 - 120 °
<td></td><td></td><td></td><td></td><td>N 33 0</td><td></td><td>CM B O</td>
<td></td><td></td><td>33 33 0 0 Vx / 101 zz 1</td><td>33 0</td><td>EC O b O O \ /<sup>2</sup>\ / 101 2 2</td><td></td><td>B ü CM »B BO oo \ /<sup>z</sup>\ / 101 2 ^^ 2</td>
<td></td><td></td><td>Ö CÖ CÖ</td><td></td><td>1 B</td><td>e O</td><td>B</td>
<td></td><td></td><td>'S 5 ? O G 1 z o «</td><td>ec O O /</td><td>O O B Z N</td><td>B O O 1</td><td>§ O e Z CM</td>
<td></td><td></td><td>O = Q co \ _ /</td><td></td><td>CO _ /</td><td><sup>a</sup> \</td><td>W _ /</td>
<td></td><td></td><td>/ Rx \ \ 0 /</td><td><<</td><td></td><td>/</td><td>O)</td>
<td></td><td>kg / ha</td><td>0.1</td><td colspan="2">0.1</td><td colspan="2">0.1</td>
<td></td><td>After sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td></td><td>bush beans</td><td>9C</td><td></td><td>6C.9G</td><td></td><td>4C, 8G, 6Y</td>
<td></td><td>cotton</td><td>9C</td><td></td><td>3C, 3H, 9G</td><td></td><td>4C, 4H, 8G</td>
<td></td><td>sorghum</td><td>9C</td><td></td><td>1C.8H</td><td></td><td>2C, 8H</td>
<td></td><td>Corn</td><td>8U</td><td></td><td>3C, 9G</td><td></td><td>3C, 9H</td>
<td></td><td>soybeans</td><td>9C</td><td></td><td>6C.9G</td><td></td><td>9C</td>
<td></td><td>wheat</td><td>6C</td><td></td><td>2C.3G</td><td></td><td>1C, 4G</td>
<td></td><td>Wild oats</td><td>9C</td><td></td><td>2C, 6G</td><td></td><td>3G</td>
<td></td><td>rice</td><td>5C</td><td></td><td>4C.9G</td><td></td><td>8G</td>
<td></td><td>barnyardgrass</td><td>IOC</td><td></td><td>5C.9H</td><td></td><td>2C, 8H</td>
<td></td><td>crabgrass</td><td>9C</td><td></td><td>5G</td><td></td><td>2C, 6H</td>
<td></td><td>Morning Glory</td><td>IOC</td><td></td><td>IOC</td><td></td><td>IOC</td>
<td></td><td>cocklebur</td><td>IOC</td><td></td><td>2G</td><td></td><td>1C, 5G</td>
<td></td><td>Kassie</td><td>9C</td><td></td><td>3C, 5G</td><td></td><td>IC</td>
<td></td><td>Cyprus grass</td><td>IOC</td><td></td><td>2C, 8G</td><td></td><td>1C, 8G</td>
<td></td><td>Before sprouting</td><td></td><td></td><td></td><td></td><td></td>
<td></td><td>sorghum</td><td>7C.9H</td><td></td><td>9G</td><td></td><td>2C, 8H</td>
<td></td><td>Corn</td><td>10H</td><td></td><td>2C, 9G</td><td></td><td>9H</td>
<td></td><td>soybeans</td><td>9H</td><td></td><td>3C, 9G</td><td></td><td>2C, 9H</td>
<td></td><td>wheat</td><td>9H</td><td></td><td>9G</td><td></td><td>8G</td>
<td></td><td>Wild oats</td><td>5C.9G</td><td></td><td>9G</td><td></td><td>1C, 7G</td>
<td></td><td>rice</td><td>10E</td><td></td><td>10E</td><td></td><td>9H</td>
<td></td><td>barnyardgrass</td><td>SC, 9H</td><td></td><td>4C, 9H</td><td></td><td>4C, 9H</td>
<td></td><td>crabgrass</td><td>5C, 9G</td><td></td><td>2C.4G</td><td></td><td>3G</td>
<td></td><td>Morning Glory</td><td>9H</td><td></td><td>9G</td><td></td><td>9G</td>
<td></td><td>cocklebur</td><td>9H</td><td></td><td>9H</td><td></td><td>9H</td>
<td></td><td>Kassie</td><td>5C, 9G</td><td></td><td>8G</td><td></td><td>8H</td>
<td></td><td>Cyprus grass</td><td>10E</td><td></td><td>9G</td><td></td><td>8G</td>
- 92 No.371668
Test B
Two pear-shaped troughs were filled with fertilized and limed Fallsington mud linden. The one trough was planted with seeds of corn, sorghum, Kentucky cattle grass and various grass weeds. The other trough was planted with seeds of soybean, purple cypress (Cyperus rotundus) and seeds of various broadleaf weeds. Seeds of the following grassy and broadleaf weed species have been planted: Crabgrass (Digitaria sanguinalis), millet (Echinochloa crusgalli), wild oats (Avena fatua), Dallis grass Paspalam dilatatum), Johnson grass (Sorghum halepense), giant foxtail (Setaria faberii), Kentucky cattle grass (Poa pratensis), dry trifets (Bromus secalinus), mustard ( Brassica arvensis), woodpeckers (Xanthium pennsylvanicum), goosefoot (Amaranthus retroflexus), morning glory (Ipomoea hederacea), cassia (Cassia tora), tea weed (Sida spinosa), common springwort (Abutilon theophrasti), and common. Datura (Datura stramonium). A smaller pot was also filled with prepared soil and planted with rice and wheat seed. Another small pot was planted with sugar beet seeds. The above four containers were treated prior to sprouting with solutions of the 15 new compounds in a non-phytotoxic solvent (ie, the solutions of the compound were sprayed onto the soil surface prior to seed germination). Duplicate seed containers described above were prepared and used as controls without treatment.
Days after treatment, the treated and the control plants were evaluated; the data obtained are given in Table XIII.
Nr.371668
Table XIII
<img file="AT371668B_D0066.tif" />
- 94 No.371668
Table XIII (continued)
<td>Before the s</td><td>Prießen</td><td colspan="4">on Fallsington mud clay</td>
<td></td><td></td><td colspan="2">/ (J 2-SOj-NH-C-NH - '- <0 COCH,</td><td>N- - <c N-</td><td>.Z<sup>B</sup>' )> Zech<sub>3</sub></td>
<td>kg / ha</td><td colspan="2">1.16</td><td colspan="3">1.4</td>
<td>crabgrass</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>barnyardgrass</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>sorghum</td><td></td><td>10E</td><td></td><td>10E</td><td></td>
<td>Wild oats</td><td></td><td>7G, 5C</td><td></td><td>8G, 8C</td><td></td>
<td>Johnson grass</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>Dalli grass</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>Giant foxtail</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>Ky. cattle grass</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>Trockentrespen</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>sugar beets</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>Corn</td><td></td><td>10E</td><td></td><td>10E</td><td></td>
<td>mustard</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>barnacles</td><td></td><td>8G.5H</td><td></td><td>8G.8H</td><td></td>
<td>goosefoot</td><td></td><td>10E</td><td></td><td>10E</td><td></td>
<td>Cyprus grass</td><td></td><td>10E</td><td></td><td>10E</td><td></td>
<td>cotton</td><td></td><td>10E</td><td></td><td>10E</td><td></td>
<td>Morning Glory</td><td></td><td>8G</td><td></td><td>8G, 8C</td><td></td>
<td>Kassie</td><td></td><td>8G.5C</td><td></td><td>8G, 8C</td><td></td>
<td>Teeunkraut</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>velvetleaf</td><td></td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>Weight of datura</td><td></td><td>8G</td><td></td><td>8G</td><td></td>
<td>soybeans</td><td></td><td>8G.8C</td><td></td><td>8G, 8C</td><td></td>
<td>rice</td><td></td><td>10E</td><td></td><td>10E</td><td></td>
<td>wheat</td><td></td><td>9G, 9H</td><td></td><td>10H</td><td></td>
- 95 No.371668
Table XIII (continued)
<td colspan="4">Before sprouting on Fallsington mud clay</td>
<td></td><td></td><td></td><td>OCH</td>
<td></td><td></td><td>0 II</td><td>"- /</td>
<td></td><td><O></td><td>-so<sub>2</sub>-nh-c-nh -</td><td>- <o)</td>
<td></td><td>\</td><td></td><td>\</td>
<td></td><td></td><td><sup>x</sup>cooch<sub>3</sub></td><td>CH<sub>3</sub></td>
<td>kg / ha</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>crabgrass</td><td>8G, 3C</td><td>9G.9C</td><td>IOC</td>
<td>barnyardgrass</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>sorghum</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Wild oats</td><td>8G, 8C</td><td>IOC</td><td>9G.9C</td>
<td>Johnson grass</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Dalli grass</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Giant foxtail</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Ky. cattle grass</td><td>IOC</td><td>10E</td><td>10E</td>
<td>Trockentrespen</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>sugar beets</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>mustard</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>8G</td><td>8G, 8C</td><td>8G, 7C</td>
<td>goosefoot</td><td>-</td><td>-</td><td>-</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td>10E</td>
<td>cotton</td><td>9G, 9C</td><td>IOC</td><td>9G.9C</td>
<td>Morning Glory</td><td>8G.8C</td><td>IOC</td><td>IOC</td>
<td>Kassie</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Teeunkraut</td><td>-</td><td>-</td><td>-</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>9G.9C</td><td>IOC</td><td>IOC</td>
<td>soybeans</td><td>IOC</td><td>9G, 9C</td><td>8G, 5C</td>
<td>rice</td><td>10E</td><td>10E</td><td>1NC</td>
<td>wheat</td><td>8G.8C</td><td>IOC</td><td>IOC</td>
- 96 No.371668
Table XIII (continued)
<td colspan="4">Before sprouting on Fallsington mud clay</td>
<td></td><td colspan="3">OCH,<sup>0</sup> / <O> -<sup>so</sup>> -nh-c-nh __ /<sup>N</sup> Q \ - \ N - < ^ COOCH, \<sub>0CHj</sub></td>
<td>kg / ha</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>crabgrass barnyardgrass sorghum Wild oats Johnson grass Dalli grass Giant foxtail Ky. cattle grass Trockentrespen sugar beets Corn mustard barnacles goosefoot Cyprus grass cotton Morning Glory Kassie Teeunkraut velvetleaf Weight of datura soybeans rice wheat</td><td>8G.5C IOC 9G.9C 5G 9G.9C 5G 8G IOC IOC IOC 7G.3C IOC 7G 10E 7G 8G, 8C IOC IOC IOC 8G, 5C IOC IOC</td><td>8G.5C IOC IOC 7G.5C IOC 7G 9G, 9C 10E IOC IOC 7G.5C IOC 8G.SC 10E 7G IOC IOC IOC 8G.8C 8G, 5C IOC 8G.8C</td><td>IOC IOC IOC 6G.5C IOC 8G.8C IOC 10E IOC IOC IOC IOC 8G.7C 10E 7G 9G, 9C IOC IOC IOC 8G.5C 10E IOC</td>
- 97 No.371668
Table XIII (continued)
<td colspan="4">Before sprouting on Fallsington mud clay</td>
<td></td><td colspan="2">/ r> \ II / ' / -<sup>S</sup>° * <sup>NH</sup><sup>C</sup><sup>NH</sup> - \ 'COOCHj</td><td>, och<sub>3</sub>'Ö></td>
<td>kg / ha</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>crabgrass</td><td>7G, 3C</td><td>9G, 9C</td><td>IOC</td>
<td>barnyardgrass</td><td>9G, 9C</td><td>IOC</td><td>IOC</td>
<td>sorghum</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Wild oats</td><td>4G</td><td>5G, 3C</td><td>IOC</td>
<td>Johnson grass</td><td>7G, 7C</td><td>8G.8C</td><td>IOC</td>
<td>Dalli grass</td><td>0</td><td>4G, 3C</td><td>6G</td>
<td>Giant foxtail</td><td>7G, 3C</td><td>8G.5C</td><td>IOC</td>
<td>Ky. cattle grass</td><td>IOC</td><td>10E</td><td>10E</td>
<td>Trockentrespen</td><td>7G</td><td>8G.8C</td><td>IOC</td>
<td>sugar beets</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>7G, 5C</td><td>IOC</td><td>IOC</td>
<td>mustard</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>8G, 9C</td><td>8G, 5C</td><td>8G, 5C</td>
<td>goosefoot</td><td>-</td><td>-</td><td>-</td>
<td>Cyprus grass</td><td>7G</td><td>7G</td><td>8G</td>
<td>cotton</td><td>IOC</td><td>8G, 5C</td><td>IOC</td>
<td>Morning Glory</td><td>8G, 8C</td><td>9G, 9C</td><td>IOC</td>
<td>Kassie</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Teeunkraut</td><td>-</td><td>-</td><td>-</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>8G.5C</td><td>9G.8C</td><td>9G.9C</td>
<td>soybeans</td><td>IOC</td><td>8G.5C</td><td>8G.8C</td>
<td>rice</td><td>8G.8C</td><td>IOC</td><td>IOC</td>
<td>wheat</td><td>3G</td><td>4G</td><td>5G</td>
Nr.371668
Table XIII (continued)
<td colspan="4">Before sprouting on Fallsington mud clay</td>
<td></td><td colspan="3">/ OCH, \O/-<sup>S0</sup>* -<sup>NH</sup>-C-NH-ζ Q \ COOCH, ^ OCH 3</td>
<td>kg / ha</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>crabgrass barnyardgrass sorghum Wild oats Johnson grass Dalli grass Riesenfuschsschwanz Ky. cattle grass Trockentrespen sugar beets Corn mustard barnacles goosefoot Cyprus grass cotton Morning Glory Kassie Teeunkraut velvetleaf Weight of datura soybeans rice wheat</td><td>7G 3G 7G 0 6G 0 6G.3C 7G, 3C 3G IOC 6G, 5H IOC 8G, 3C 7G IOC 8G.8C IOC 7G.8C 9G.9C 8G.7C 6G, 5C 0</td><td>8G, 5C 7G.7C 9G.8C IOC 7G.7C 0 5G.3C 8G.5C 3G IOC 7G.5C IOC IOC 7G, 3C 8G IOC IOC 8G.9C IOC 9G, 8C 8G, 8C 2G</td><td>IOC 9G, 9C IOC 5G.3C 8G, 8C 3G 8G, 8C IOC 6G, 3C IOC IOC IOC 8G, 5C 8G 9G.5C IOC IOC IOC IOC 8G.5C IOC 4G.3C</td>
Nr.371668
Table XIII (continued)
Before sprouting on Fallsington mud clay
N-N <0 / - ™. <sup>N</sup> \
CH.
/ IX \
SO, NH-C-NH> r "i
COCH.
<td>kg / ha</td><td>1.16</td><td>1.4</td>
<td>crabgrass</td><td>0</td><td>5G</td>
<td>barnyardgrass</td><td>IOC</td><td>IOC</td>
<td>sorghum</td><td>IOC</td><td>IOC</td>
<td>Wild oats</td><td>0</td><td>5G</td>
<td>Johnson grass</td><td>IOC</td><td>IOC</td>
<td>Dalli grass</td><td>5G</td><td>8G, 3C</td>
<td>Giant foxtail</td><td>3G</td><td>6G</td>
<td>Ky. cattle grass</td><td>8G</td><td>10E</td>
<td>Dry trespen</td><td>10E</td><td>10E</td>
<td>sugar beets</td><td>7G</td><td>IOC</td>
<td>Corn</td><td>4G</td><td>8G.8C</td>
<td>mustard</td><td>10E</td><td>10E</td>
<td>barnacles</td><td>7G</td><td>8G</td>
<td>goosefoot</td><td>10E</td><td>10E</td>
<td>Cyprus grass</td><td>6G</td><td>10E</td>
<td>cotton</td><td>4G</td><td>7G</td>
<td>Morning Glory</td><td>4G</td><td>10E</td>
<td>Kassie</td><td>5G</td><td>7G.2C</td>
<td>Teeunkraut</td><td>0</td><td>8G, 5C</td>
<td>velvetleaf</td><td>5G</td><td>7G</td>
<td>Weight of datura</td><td>2G</td><td>6G</td>
<td>soybeans</td><td>7G, 7H</td><td>8G, 8H</td>
<td>rice</td><td>10E</td><td>10E</td>
<td>wheat</td><td>2G</td><td>8G, 5C</td>
- 100
Nr.371668
Table XIII (continued)
<td colspan="4">Before sprouting on Fallsington mud clay</td>
<td></td><td><sup>cfl</sup>A J- /<sup>Q</sup>- ch<sub>3</sub>ct</td><td>M 0 % II C-NH-C-NH-SOj-N<sup>Z</sup>CH-OC II 0</td><td><O)</td>
<td>kg / ha</td><td>1/32</td><td>1.16</td><td>1.4</td>
<td>crabgrass</td><td>0</td><td>4G</td><td>7G</td>
<td>barnyardgrass</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>sorghum</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Wild oats</td><td>8G.7C</td><td>8G.8C</td><td>IOC</td>
<td>Johnson grass</td><td>9G.9C</td><td>IOC</td><td>IOC</td>
<td>Dalli grass</td><td>0</td><td>0</td><td>6G</td>
<td>Giant foxtail</td><td>4G, 3H</td><td>5G, 5H</td><td>9G.9C</td>
<td>Ky. cattle grass</td><td>10E</td><td>10E</td><td>10E</td>
<td>Trockentrespen</td><td>8G, 9C</td><td>10E</td><td>10E</td>
<td>sugar beets</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>8G.8C</td><td>IOC</td><td>IOC</td>
<td>mustard</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>7G.2C</td><td>7G.5H</td><td>7G.5H</td>
<td>goosefoot</td><td>10E</td><td>10E</td><td>10E</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td>10E</td>
<td>cotton</td><td>7G</td><td>8G</td><td>8G</td>
<td>Morning Glory</td><td>5G</td><td>7G</td><td>8G</td>
<td>Kassie</td><td>7G</td><td>8G, 3C</td><td>8G, 8C</td>
<td>Teeunkraut</td><td>7G</td><td>7G</td><td>IOC</td>
<td>velvetleaf</td><td>8G.7C</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>7G</td><td>7G</td><td>8G, 5C</td>
<td>soybeans</td><td>8G, 3H</td><td>7G.5H</td><td>9G.9C</td>
<td>rice</td><td>10E</td><td>10E</td><td>10E</td>
<td>wheat</td><td>4G.2C</td><td>6G.4C</td><td>7G.4C</td>
- 101 no. 371668
Table XIII (continued)
<td colspan="4">Before sprouting on Fallsington mud clay</td>
<td></td><td colspan="3">.CH, / <S \ II /<sup>N</sup><~ Ä \ \ U / - SOj-NH-C-NH-- / Q ' \ COONa <sup>CH</sup>a</td>
<td>kg / ha</td><td>1/32</td><td>1.16</td><td>1.4</td>
<td>crabgrass barnyardgrass sorghum Wild oats Johnson grass Dalli grass Giant foxtail Ky. cattle grass Trockentrespen sugar beets Corn mustard barnacles goosefoot Cyprus grass cotton Morning Glory Kassie Teeunkraut velvetleaf Weight of datura soybeans rice wheat</td><td>0 0 0 0 0 0 0 0 0 6G, 3H 0 0 0 0 0 0 0 0 0 0 0 0 0 0</td><td>0 0 0 0 0 0 0 0 0 IOC 0 0 0 0 0 0 0 0 0 0 0 0 0 0</td><td>0 0 0 0 0 0 0 0 6G 7G, 5H 0 5G 0 5G 5G 0 0 0 0 0 0 0 6G, 5C 0</td>
- 102 No.371668
Table XIIX (continued)
<td colspan="6">Before sprouting on Fallsington mud clay</td>
<td></td><td colspan="3"><sup>c</sup>H<sub>3</sub><\ ^ /<sup>G =</sup>> - CH (</td><td colspan="2">0 II CO- (CH,). CH, 0 \ II / <λ \ , C-NH-C-NH-SO, - / \ -N <sup>x</sup>'</td>
<td>kg / ha</td><td colspan="2">1/32</td><td colspan="2">1.16</td><td>1.4</td>
<td>crabgrass</td><td>0</td><td></td><td></td><td>0</td><td>4G</td>
<td>barnyardgrass</td><td>7G.3C</td><td></td><td></td><td>8G.3C</td><td>IOC</td>
<td>sorghum</td><td>6G, 3H</td><td></td><td></td><td>5G</td><td>IOC</td>
<td>Wild oats</td><td>0</td><td></td><td></td><td>0</td><td>6G, 3C</td>
<td>Johnson grass</td><td>0</td><td></td><td></td><td>0</td><td>5G.5H</td>
<td>Dalli grass</td><td>4G</td><td></td><td></td><td>5G</td><td>10E</td>
<td>Giant foxtail</td><td>3H</td><td></td><td></td><td>3H</td><td>10H</td>
<td>Ky. cattle grass</td><td>9G</td><td></td><td></td><td>10E</td><td>10E</td>
<td>Trockentrespen</td><td>0</td><td></td><td></td><td>2G</td><td>8G.8C</td>
<td>sugar beets</td><td>4G</td><td></td><td></td><td>4G</td><td>7G.7C</td>
<td>Corn</td><td>0</td><td></td><td></td><td>4G</td><td>5G, 5H</td>
<td>mustard</td><td>9G</td><td></td><td></td><td>9G, 5C</td><td>IOC</td>
<td>barnacles</td><td>3H</td><td></td><td></td><td>2H</td><td>5G, 5H</td>
<td>goosefoot</td><td>10E</td><td></td><td></td><td>10E</td><td>10E</td>
<td>Cyprus grass</td><td>5G</td><td></td><td></td><td>5G</td><td>8G</td>
<td>cotton</td><td>0</td><td></td><td></td><td>0</td><td>3G, 3H</td>
<td>Morning Glory</td><td>3G</td><td></td><td></td><td>6G</td><td>4G</td>
<td>Kassie</td><td>0</td><td></td><td></td><td>0</td><td>3G</td>
<td>Teeunkraut</td><td>-</td><td></td><td></td><td>-</td><td>5G, 5H</td>
<td>Griswurz</td><td>7G, 7C</td><td></td><td></td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>0</td><td></td><td></td><td>2G</td><td>4G</td>
<td>soybeans</td><td>0</td><td></td><td></td><td>0</td><td>6G, 6H</td>
<td>rice</td><td>9G, 9C</td><td></td><td></td><td>7G.5C</td><td>10E</td>
<td>wheat</td><td>3G</td><td></td><td></td><td>4G</td><td>6G</td>
- 103 No.371668
Table XIII (continued)
<td colspan="4">Before sprouting on Fallsington mud clay</td>
<td></td><td></td><td colspan="2">0</td>
<td></td><td>X ch<sub>5</sub>O</td><td colspan="2">j | CO-CH (CH) \ 3 2 M 0 \ Λ li / 7S C-NH-C-NH-SO, -i fj 2 N =<sup>Z</sup> '- /</td>
<td>kg / ha</td><td>1/32</td><td>1.16</td><td>1.4</td>
<td>crabgrass</td><td>0</td><td>0</td><td>6G</td>
<td>barnyardgrass</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>sorghum</td><td>9G.9C</td><td>IOC</td><td>IOC</td>
<td>Wild oats</td><td>2G</td><td>6G</td><td>7G.5C</td>
<td>Johnson grass</td><td>8G.8C</td><td>IOC</td><td>IOC</td>
<td>Dalli grass</td><td>0</td><td>0</td><td>5G.3H</td>
<td>Giant foxtail</td><td>3H</td><td>4G.3H</td><td>IOC</td>
<td>Ky. cattle grass</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Trockentrespen</td><td>5G</td><td>8G, 8C</td><td>10E</td>
<td>sugar beets</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>6G.3H</td><td>7G.7H</td><td>IOC</td>
<td>mustard</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>7G.5H</td><td>8G.5H</td><td>8G.5H</td>
<td>goosefoot</td><td>10E</td><td>10E</td><td>1NC</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td>1NC</td>
<td>cotton</td><td>6G</td><td>7G</td><td>9G</td>
<td>Morning Glory</td><td>8G</td><td>8G</td><td>IOC</td>
<td>Kassie</td><td>8G</td><td>8G.5H</td><td>IOC</td>
<td>Teeunkraut</td><td>0</td><td>6G.5C</td><td>IOC</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>8G, 3C</td><td>8G, 5C</td><td>8G.5C</td>
<td>soybeans</td><td>7G.5H</td><td>7G.5H</td><td>9G.5H</td>
<td>rice</td><td>8G, 8C</td><td>IOC</td><td>10E</td>
<td>wheat</td><td>2G</td><td>4G</td><td>6G</td>
- 104 No. 371668
Table XIII (continued)
<td>Before the</td><td colspan="2">Sprout on Fallsington mud clay</td><td></td>
<td></td><td></td><td rowspan="2">0 II c- v Q</td><td></td>
<td></td><td>CH, 0 Y "-</td><td>O-CH (CH,)<sub>ä</sub>Y</td>
<td></td><td colspan="2">'/% II HC C-NH-C-NH-SOj- CH,</td><td>- <Q></td>
<td>kg / ha</td><td>1/32</td><td>1.16</td><td>1.4</td>
<td></td><td></td><td></td><td></td>
<td>crabgrass</td><td>0</td><td>2G</td><td>7G</td>
<td>barnyardgrass</td><td>IOC</td><td>IOC</td><td>10E</td>
<td>sorghum</td><td>IOC</td><td>10E</td><td>10E</td>
<td>Wild oats</td><td>4G</td><td>7G, 3C</td><td>IOC</td>
<td>Johnson grass</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Dalli grass</td><td>5G</td><td>7G</td><td>IOC</td>
<td>Giant foxtail</td><td>6G, 3H</td><td>9G.9C</td><td>IOC</td>
<td>Ky. cattle grass</td><td>IOC</td><td>10E</td><td>10E</td>
<td>Trockentrespen</td><td>10E</td><td>10E</td><td>10E</td>
<td>sugar beets</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>mustard</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>8G, 5H</td><td>8G.5H</td><td>8G.8H</td>
<td>goosefoot</td><td>10E</td><td>10E</td><td>10E</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td><td>10E</td>
<td>cotton</td><td>6G.3H</td><td>8G.6C</td><td>8G.6C</td>
<td>Morning Glory</td><td>9G</td><td>9G</td><td>IOC</td>
<td>Kassie</td><td>8G.8C</td><td>8G, 5C</td><td>8G, 9C</td>
<td>Teeunkraut</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>8G, 5C</td><td>8G.7C</td><td>8G, 8C</td>
<td>soybeans</td><td>8G, 5H</td><td>9G.5H</td><td>9G.5H</td>
<td>rice</td><td>8G.9C</td><td>IOC</td><td>10E</td>
<td>wheat</td><td>BG</td><td>BG.5C</td><td>IOC</td>
105 Nr.371668
Table XIII (continued)
Before sprouting on Fallsington mud clay
<img file="AT371668B_D0067.tif" />
kg / ha
crabgrass
barnyardgrass
sorghum
Wild oats
Johnson grass
Dalli grass
Giant foxtail
Ky. cattle grass
Trockentrespen
sugar beets
Corn
mustard
barnacles
goosefoot
Cyprus grass
cotton
Morning Glory
Kassie
Teeunkraut
Courgette Gew. Datura Soybeans
rice
wheat
<td>1/32</td><td>1.16</td><td>1.4</td>
<td>0</td><td>4G</td><td>8G</td>
<td>0</td><td>6G, 3H</td><td>8C, 5H</td>
<td>6G, 3H</td><td>7G.3H</td><td>IOC</td>
<td>0</td><td>0</td><td>5G, 3C</td>
<td>2H</td><td>2H</td><td>8G.5H</td>
<td>0</td><td>0</td><td>4G</td>
<td>0</td><td>0</td><td>7G</td>
<td>5G.6C</td><td>7G.8C</td><td>10E</td>
<td>0</td><td>6G.3C</td><td>7G.8C</td>
<td>IOC</td><td>IOC</td><td>IOC</td>
<td>7G.7H</td><td>IOC</td><td>IOC</td>
<td>IOC</td><td>IOC</td><td>IOC</td>
<td>8G.8H</td><td>8G.8H</td><td>8G, 8H</td>
<td>10E</td><td>10E</td><td>10E</td>
<td>10E</td><td>10E</td><td>10E</td>
<td>8G</td><td>8G</td><td>IOC</td>
<td>IOC</td><td>IOC</td><td>IOC</td>
<td>8G.9C</td><td>IOC</td><td>IOC</td>
<td>IOC</td><td>IOC</td><td>IOC</td>
<td>IOC</td><td>IOC</td><td>IOC</td>
<td>8G, 8C</td><td>IOC</td><td>8G, 9C</td>
<td>9G.5H</td><td>9G, 5H</td><td>9G.5H</td>
<td>5G.3C</td><td>5G, 3C</td><td>7G.4C</td>
<td>0</td><td>0</td><td>2G</td>
- 106 No.371668
Table XIXI (continued)
<td colspan="4">Before sprouting on Fallsington mud clay</td>
<td></td><td></td><td></td><td rowspan="2">0 II ch> ch<sub>3</sub>'-ΧΟ / -<sup>01</sup></td>
<td></td><td colspan="2">CH, 0 //<sup>c</sup>~ \ ii HC C-NH-C-NH-S (<sup>x</sup>c = i / \ CH<sub>3</sub>-0</td>
<td>kg / ha</td><td>1.16</td><td colspan="2">1.4</td>
<td>crabgrass</td><td>3H</td><td></td><td>6G</td>
<td>barnyardgrass</td><td>6G.4C</td><td></td><td>IOC</td>
<td>sorghum</td><td>IOC</td><td></td><td>IOC</td>
<td>Wild oats</td><td>6G</td><td></td><td>8G.5C</td>
<td>Johnson grass</td><td>6G, 3H</td><td></td><td>8G, 8C</td>
<td>Dalli grass</td><td>0</td><td></td><td>4G</td>
<td>Giant foxtail</td><td>3H</td><td></td><td>6G.2C</td>
<td>Ky. cattle grass</td><td>8G</td><td></td><td>10E</td>
<td>Dry trespen</td><td>10E</td><td></td><td>10E</td>
<td>sugar beets</td><td>8G, 8C</td><td></td><td>IOC</td>
<td>Corn</td><td>5G, 5H</td><td></td><td>9G.9C</td>
<td>mustard</td><td>IOC</td><td></td><td>IOC</td>
<td>barnacles</td><td>8G.5H</td><td></td><td>8G.3H</td>
<td>goosefoot</td><td>IOC</td><td></td><td>IOC</td>
<td>Cyprus grass</td><td>10E</td><td></td><td>10E</td>
<td>cotton</td><td>5G</td><td></td><td>5G</td>
<td>Frunkwinde</td><td>6G</td><td></td><td>8G.8C</td>
<td>Kassie</td><td>4G</td><td></td><td>8G, 8C</td>
<td>Teeunkraut</td><td>6G, 5C</td><td></td><td>IOC</td>
<td>velvetleaf</td><td>8G.8C</td><td></td><td>IOC</td>
<td>Weight of datura</td><td>5G, 3H</td><td></td><td>IOC</td>
<td>soybeans</td><td>8G, 8C</td><td></td><td>8G.8C</td>
<td>rice</td><td>10E</td><td></td><td>10E</td>
<td>wheat</td><td>0</td><td></td><td>3G</td>
- 107 No.371668
Table XIII (continued)
<td colspan="5">Before sprouting on Fallsington mud clay</td>
<td></td><td colspan="2">ch<sub>3</sub>O ί HC C-NH-C-NH-SO, - > = N<sup>Z</sup></td><td>0 II CO-CH \ - <Q></td><td>- CI</td>
<td></td><td>ch<sub>3</sub><sup>X</sup></td><td></td><td></td><td></td>
<td>kg / ha</td><td>1.16</td><td colspan="3">1.4</td>
<td>crabgrass</td><td>0</td><td></td><td>6G</td><td></td>
<td>barnyardgrass</td><td>6G, 3H</td><td></td><td>IOC</td><td></td>
<td>sorghum</td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>Wild oats</td><td>6G</td><td></td><td>IOC</td><td></td>
<td>Johnson grass</td><td>6G, 3H</td><td></td><td>IOC</td><td></td>
<td>Dalli grass</td><td>0</td><td></td><td>5G</td><td></td>
<td>Giant foxtail</td><td>2H</td><td></td><td>5G.2C</td><td></td>
<td>Ky. cattle grass</td><td>9G</td><td></td><td>10E</td><td></td>
<td>Trockentrespen</td><td>10E</td><td></td><td>10E</td><td></td>
<td>sugar beets</td><td>7G.8C</td><td></td><td>IOC</td><td></td>
<td>Corn</td><td>6G, 5H</td><td></td><td>9G.9C</td><td></td>
<td>mustard</td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>barnacles</td><td>6G, 2C</td><td></td><td>8G, 3C</td><td></td>
<td>goosefoot</td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>Cyprus grass</td><td>10E</td><td></td><td>10E</td><td></td>
<td>cotton</td><td>3G</td><td></td><td>8G</td><td></td>
<td>Morning Glory</td><td>4G</td><td></td><td>IOC</td><td></td>
<td>Kassie</td><td>3G</td><td></td><td>6G</td><td></td>
<td>Teeunkraut</td><td>IOC</td><td></td><td>IOC</td><td></td>
<td>velvetleaf</td><td>8G</td><td></td><td>IOC</td><td></td>
<td>Weight of datura</td><td>8G.8C</td><td></td><td>IOC</td><td></td>
<td>soybeans</td><td>7G, 5H</td><td></td><td>9G.9C</td><td></td>
<td>rice</td><td>8G, 8C</td><td></td><td>10E</td><td></td>
<td>wheat</td><td>3G</td><td></td><td>5G, 2C</td><td></td>
- 108 No.371668
Table XIII (continued)
<td colspan="5">Before sprouting on Fallsington mud clay</td>
<td></td><td>ch<sub>3</sub>o ^ /<sup>c</sup>= > - GH,</td><td>// N</td><td>C 1 'NH-C (CH</td><td><0 / z<sup>-</sup>), -CH-OC II 0</td>
<td>kg / ha</td><td colspan="3">1.16</td><td>1.4</td>
<td>crabgrass</td><td>6G</td><td></td><td></td><td>7G</td>
<td>barnyardgrass</td><td>8G.4C</td><td></td><td></td><td>8G.6H</td>
<td>sorghum</td><td>9G.8C</td><td></td><td></td><td>IOC</td>
<td>Wild oats</td><td>6G.2C</td><td></td><td></td><td>8G.5C</td>
<td>Johnson grass</td><td>8G.2C</td><td></td><td></td><td>IOC</td>
<td>Dalli grass</td><td>3G</td><td></td><td></td><td>5G</td>
<td>Giant foxtail</td><td>6G</td><td></td><td></td><td>8G.4C</td>
<td>Ky. cattle grass</td><td>9G</td><td></td><td></td><td>10E</td>
<td>Trockentrespen</td><td>7G</td><td></td><td></td><td>IOC</td>
<td>sugar beets</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>Corn</td><td>9G, 9C</td><td></td><td></td><td>IOC</td>
<td>mustard</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>barnacles</td><td>8G, 8C</td><td></td><td></td><td>8G.8C</td>
<td>goosefoot</td><td>10E</td><td></td><td></td><td>10E</td>
<td>Cyprus grass</td><td>7G</td><td></td><td></td><td>9G</td>
<td>cotton</td><td>9G.5H</td><td></td><td></td><td>9G.5H</td>
<td>Morning Glory</td><td>9G.9C</td><td></td><td></td><td>9G, 9C</td>
<td>Kassie</td><td>8G.9C</td><td></td><td></td><td>IOC</td>
<td>Teeunkraut</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>velvetleaf</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>Weight of datura</td><td>5G</td><td></td><td></td><td>8G, 7C</td>
<td>soybeans</td><td>9G.9C</td><td></td><td></td><td>9G.9C</td>
<td>rice</td><td>6G.3C</td><td></td><td></td><td>8G.8C</td>
<td>wheat</td><td>0</td><td></td><td></td><td>0</td>
109
Nr.371668
Table XIII (continued)
<td colspan="3">Before sprouting on Fallsington mud clay</td>
<td></td><td>CH, 0</td><td></td>
<td></td><td>'V <sub>M</sub> 0</td><td></td>
<td></td><td>.C = N π</td><td>-</td>
<td></td><td>/ \ II</td><td></td>
<td></td><td colspan="2">HC. , C-NH-C-NH-SO<sub>2</sub>- '2</td>
<td></td><td>z</td><td>z</td>
<td></td><td colspan="2">CH 0 ci-ch<sub>2</sub> ch<sub>2</sub>-oo<sup>3</sup></td>
<td></td><td></td><td>0</td>
<td>kg / ha</td><td>1.16</td><td>1.4</td>
<td>crabgrass</td><td>0</td><td>6G</td>
<td>barnyardgrass</td><td>IOC</td><td>IOC</td>
<td>sorghum</td><td>IOC</td><td>IOC</td>
<td>Wild oats</td><td>8G.3C</td><td>8G, 3C</td>
<td>Johnson grass</td><td>9G, 3C</td><td>IOC</td>
<td>Dalli grass</td><td>4G</td><td>8G, 5C</td>
<td>Giant foxtail</td><td>IOC</td><td>IOC</td>
<td>Ky. cattle grass</td><td>10E</td><td>10E</td>
<td>Dry trespen</td><td>IOC</td><td>10E</td>
<td>sugar beets</td><td>9G, 9C</td><td>9G.9C</td>
<td>Corn</td><td>5G, 3H</td><td>7G.7H</td>
<td>mustard</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>7G, 5H</td><td>8G.5C</td>
<td>goosefoot</td><td>10E</td><td>10E</td>
<td>Cyprus grass</td><td>10E</td><td>10E</td>
<td>cotton</td><td>3G</td><td>8G</td>
<td>Morning Glory</td><td>5G</td><td>IOC</td>
<td>Kassie</td><td>7G, 5C</td><td>8G.7C</td>
<td>Teeunkraut</td><td>3Η</td><td>7G, 5H</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>5G</td><td>7G</td>
<td>soybeans</td><td>8G.8H</td><td>9G.9H</td>
<td>rice</td><td>IOC</td><td>10E</td>
<td>wheat</td><td>5G</td><td>6G</td>
- 110 No.371668
Table XIII (continued)
<td colspan="5">Before sprouting on Fallsington mud clay</td>
<td></td><td>CH<sub>3</sub>O ^ HC • Z</td><td colspan="2">-Μ θ \ II JG-NH-C-NH-SO N = Cl-CH, CH, -02 2</td><td>11 0</td>
<td>kg / ha</td><td colspan="2">1.16</td><td colspan="2">1.4</td>
<td>crabgrass</td><td>0</td><td></td><td></td><td>4G</td>
<td>barnyardgrass</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>sorghum</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>Wild oats</td><td>8G.2C</td><td></td><td></td><td>8G, 6C</td>
<td>Johnson grass</td><td>9G.9C</td><td></td><td></td><td>IOC</td>
<td>Dalli grass</td><td>5G</td><td></td><td></td><td>8G.9C</td>
<td>Giant foxtail</td><td>6G, 4H</td><td></td><td></td><td>IOC</td>
<td>Ky. cattle grass</td><td>10E</td><td></td><td></td><td>10E</td>
<td>Trockentrespen</td><td>10E</td><td></td><td></td><td>10E</td>
<td>sugar beets</td><td>9G, 9C</td><td></td><td></td><td>9G.9C</td>
<td>Corn</td><td>9G, 9C</td><td></td><td></td><td>9G.9C</td>
<td>mustard</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>barnacles</td><td>8G, 5H</td><td></td><td></td><td>7G.5H</td>
<td>goosefoot</td><td>10E</td><td></td><td></td><td>10E</td>
<td>Cyprus grass</td><td>10E</td><td></td><td></td><td>10E</td>
<td>cotton</td><td>6C.2H</td><td></td><td></td><td>8G.5H</td>
<td>Morning Glory</td><td>IOC</td><td></td><td></td><td>8G, 5C</td>
<td>Kassie</td><td>7G, 3C</td><td></td><td></td><td>8G, 7C</td>
<td>Teeunkraut</td><td>9G, 9C</td><td></td><td></td><td>10G</td>
<td>velvetleaf</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>Gew.Stechapfel</td><td>6C</td><td></td><td></td><td>8G, 7C</td>
<td>soybeans</td><td>8G, 8H</td><td></td><td></td><td>8G.9H</td>
<td>rice</td><td>10E</td><td></td><td></td><td>10E</td>
<td>wheat</td><td>7G</td><td></td><td></td><td>IOC</td>
- 111
Nr.371668
Table XIII (continued)
<td colspan="4">Before sprouting on Fallsington mud clay</td>
<td></td><td>ch<sub>3</sub>o ^</td><td></td><td>n</td>
<td></td><td>//<sup>c</sup>"</td><td></td><td rowspan="2"><sup>11</sup> / <S \ -C-NH-SOJ</td>
<td></td><td>N \</td><td>C-NH</td>
<td></td><td>Z -</td><td>Z</td><td>z</td>
<td></td><td>ch<sub>3</sub>O</td><td>CI</td><td>-CH.CH.-OC II 0</td>
<td>kg / ha</td><td>1.16</td><td></td><td>1.4</td>
<td>crabgrass</td><td>0</td><td></td><td>0</td>
<td>barnyardgrass</td><td>4G</td><td></td><td>4G</td>
<td>sorghum</td><td>5G</td><td></td><td>7G</td>
<td>Wild oats</td><td>3G</td><td></td><td>0</td>
<td>Johnson grass</td><td>0</td><td></td><td>6G.6E</td>
<td>Dalli grass</td><td>0</td><td></td><td>0</td>
<td>Giant foxtail</td><td>0</td><td></td><td>3H</td>
<td>Ky. cattle grass</td><td>6G</td><td></td><td>8G</td>
<td>Trockentrespen</td><td>0</td><td></td><td>3G</td>
<td>sugar beets</td><td>IOC</td><td></td><td>IOC</td>
<td>Corn</td><td>4G, 2H</td><td></td><td>7G.5H</td>
<td>mustard</td><td>9G</td><td></td><td>IOC</td>
<td>barnacles</td><td>8G.5H</td><td></td><td>8G, 5C</td>
<td>goosefoot</td><td>10E</td><td></td><td>10E</td>
<td>Cyprus grass</td><td>8G</td><td></td><td>8G</td>
<td>cotton</td><td>7G, 5H</td><td></td><td>8G.5H</td>
<td>Frunkwinde</td><td>8G</td><td></td><td>8G, 5C</td>
<td>Kassie</td><td>7G, 3C</td><td></td><td>8G.9C</td>
<td>Teeunkraut</td><td>5G.6H</td><td></td><td>IOC</td>
<td>velvetleaf</td><td>7G.7C</td><td></td><td>IOC</td>
<td>Weight of datura</td><td>3G</td><td></td><td>5G</td>
<td>soybeans</td><td>3G</td><td></td><td>6G.5H</td>
<td>rice</td><td>6G, 3C</td><td></td><td>5G, 3C</td>
<td>wheat</td><td>0</td><td></td><td>0</td>
- 112 No.371668
Table XIII (continued)
<td colspan="5">Before sprouting on Fallsington mud clay</td>
<td></td><td>gh<sub>3</sub>O Z /<sup>C</sup>> CH,</td><td colspan="3">_ .. 0 % <sup>11</sup> / 7> \ Cl-CH.CH, -OC<sup>4 4</sup> II 0</td>
<td>kg / ha</td><td colspan="2">1.16</td><td colspan="2">1.4</td>
<td>crabgrass</td><td>0</td><td></td><td></td><td>5G</td>
<td>barnyardgrass</td><td>0</td><td></td><td></td><td>7G.4C</td>
<td>sorghum</td><td>8G</td><td></td><td></td><td>IOC</td>
<td>Wild oats</td><td>3G</td><td></td><td></td><td>6G</td>
<td>Johnson grass</td><td>0</td><td></td><td></td><td>6G</td>
<td>Dalli grass</td><td>0</td><td></td><td></td><td>0</td>
<td>Giant foxtail</td><td>0</td><td></td><td></td><td>6G</td>
<td>Ky. cattle grass</td><td>8G</td><td></td><td></td><td>10E</td>
<td>Trockentrespen</td><td>3G</td><td></td><td></td><td>6G</td>
<td>sugar beets</td><td>9G.9C</td><td></td><td></td><td>IOC</td>
<td>Corn</td><td>5G, 3H</td><td></td><td></td><td>7G, 8H</td>
<td>mustard</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>barnacles</td><td>8G.5H</td><td></td><td></td><td>8G, 8C</td>
<td>goosefoot</td><td>10E</td><td></td><td></td><td>10E</td>
<td>Cyprus grass</td><td>7G</td><td></td><td></td><td>7G</td>
<td>cotton</td><td>7G</td><td></td><td></td><td>8G</td>
<td>Morning Glory</td><td>8G</td><td></td><td></td><td>8G.5C</td>
<td>Kassie</td><td>7G, 3C</td><td></td><td></td><td>8G.9C</td>
<td>Teeunkraut</td><td>5G.5H</td><td></td><td></td><td>IOC</td>
<td>velvetleaf</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>Weight of datura</td><td>3G</td><td></td><td></td><td>5G</td>
<td>soybeans</td><td>2G, 2H</td><td></td><td></td><td>7G.7H</td>
<td>rice</td><td>6G.3C</td><td></td><td></td><td>6G.3C</td>
<td>wheat</td><td>0</td><td></td><td></td><td>0</td>
Test C
Pots filled with Fallington mud were treated with soybeans, cotton, corn, rice, wheat, sorghum, alfalfa, spawn (Abutilon theophrasti), sesbania (Sesbania exal5 tata), cassia (Cassia tora), morning glory (Ipomoea haderacea), wt Datura (Datura stramonium), burdock (Xanthium pennsylvanicum), crabgrass (Digitaria spp.), Cypressgrass (Cyperus rotundus), barnyardgrass (Eohinochloa crusgalli) giant foxtail (Setaria faberii), and wild oats
- 113
No.371668 (Avena fatua). About 1 1/2 weeks after planting, the young plants and the surrounding soil were sprayed whole with the test compound dissolved in a non-phytotoxic solvent. Other groups of the same weeds and crops were sprayed with the same non-phytotoxic solvent and served as control plants. 14
Days after treatment, all treated plants were compared to the control plants and visually evaluated for response to treatment, obtaining the data of Table XIV. It should be noted that wheat shows tolerance for several compounds of this table.
Table XIV
<td colspan="6">Soil foliage treatment from above</td>
<td></td><td></td><td colspan="2">2-SOj-NH-C-NH -</td><td>- <(</td><td>^ / CH<sub>S</sub>D></td>
<td></td><td></td><td>\ s COCH<sub>3</sub></td><td></td><td>N-</td><td>^ CH,</td>
<td colspan="2">kg / ha</td><td>1.16</td><td colspan="3">1.4</td>
<td>soybeans</td><td></td><td>10G.8C</td><td></td><td></td><td>10G.7C</td>
<td>velvetleaf</td><td></td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>Sesbania</td><td></td><td>10G.9C</td><td></td><td></td><td>IOC</td>
<td>Kassie</td><td></td><td>10G.6C</td><td></td><td></td><td>10G.7C</td>
<td>cotton</td><td></td><td>10G.7C</td><td></td><td></td><td>10G.6C</td>
<td>Morning Glory</td><td></td><td>10G.7C</td><td></td><td></td><td>IOC</td>
<td>Weight of datura</td><td></td><td>10G.9C</td><td></td><td></td><td>10G, 9C</td>
<td>barnacles</td><td></td><td>10G.8C</td><td></td><td></td><td>10G.8C</td>
<td>Corn</td><td></td><td>10G.9C</td><td></td><td></td><td>IOC</td>
<td>crabgrass</td><td></td><td>10G.4C</td><td></td><td></td><td>10G.8C</td>
<td>rice</td><td></td><td>10G.4C</td><td></td><td></td><td>10G.6C</td>
<td>Cyprus grass</td><td></td><td>10G.6C</td><td></td><td></td><td>10G.7C</td>
<td>barnyardgrass</td><td></td><td>10G.8C</td><td></td><td></td><td>10G.9C</td>
<td>wheat</td><td></td><td>10G.7C</td><td></td><td></td><td>10G.7C</td>
<td>Giant foxtail</td><td></td><td>10G.7C</td><td></td><td></td><td>10G.8C</td>
<td>Wild oats</td><td></td><td>10G.8C</td><td></td><td></td><td>10G.9C</td>
<td>sorghum</td><td></td><td>10G.9C</td><td></td><td></td><td>10G.8C</td>
114 Nr.371668
Table XIV (continued)
<td colspan="4">Soil foliage treatment from above</td>
<td></td><td>CH.</td><td></td><td></td>
<td></td><td>V »</td><td>0 II</td><td></td>
<td></td><td colspan="2">\ / -nh-c-nh-so<sub>2</sub>-</td><td>- <0)</td>
<td></td><td>} -N</td><td></td><td></td>
<td></td><td>CH /</td><td colspan="2">CH<sub>3</sub> OC ^</td>
<td></td><td></td><td></td><td>0</td>
<td>kg / ha</td><td>1/500</td><td>1/250</td><td>1/128</td>
<td>soybeans</td><td>10G.8C</td><td>10G.9C</td><td>10G.9C</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Sesbania</td><td>8G, 7C</td><td>10G.8C</td><td>10G.9C</td>
<td>Kassie</td><td>8G.3C</td><td>10G.8C</td><td>10G.6C</td>
<td>cotton</td><td>10G.7C</td><td>IOC</td><td>10G.9C</td>
<td>Morning Glory</td><td>2G</td><td>6G</td><td>7G, 3C</td>
<td>alfalfa</td><td>5G</td><td>10G.6C</td><td>10G.5C</td>
<td>Weight of datura</td><td>3G</td><td>8G.3C</td><td>IOC</td>
<td>barnacles</td><td>10G</td><td>8G.2C</td><td>10G.8C</td>
<td>Corn</td><td>10G.7C</td><td>8G.3U</td><td>10G, 9C</td>
<td>crabgrass</td><td>5G</td><td>5G</td><td>6G</td>
<td>rice</td><td>10G.4C</td><td>8G.2C</td><td>10G.5C</td>
<td>Cyprus grass</td><td>10G, 3C</td><td>10G.4C</td><td>IOC</td>
<td>barnyardgrass</td><td>IOC</td><td>10G.3C</td><td>10G.8C</td>
<td>wheat</td><td>10G.9C</td><td>8G</td><td>10G.4C</td>
<td>Giant foxtail</td><td>10G.8C</td><td>8G</td><td>10G.7C</td>
<td>Wild oats</td><td>8G, 3C</td><td>8G</td><td>10G.5C</td>
<td>sorghum</td><td>10G.3C</td><td>10G.4C</td><td>10G.7C</td>
115
Nr.371668
Table XIV (continued)
<td colspan="2">Soil foliage treatment of</td><td colspan="2">above</td>
<td></td><td>CH,</td><td></td><td></td>
<td></td><td>\</td><td rowspan="2"></td><td>0</td>
<td></td><td>/ r</td><td>II /</td>
<td></td><td>Ά</td><td>) /) - NHN</td><td>C-NH-SO - λ "</td>
<td></td><td>CH,</td><td></td><td>CH OC</td>
<td></td><td></td><td></td><td><sup>ä</sup> II</td>
<td></td><td></td><td></td><td>0</td>
<td>• kg / ha '- </td><td colspan="2">1/64</td><td>1/32</td>
<td>soybeans</td><td>10G.8C</td><td></td><td>10G.8C</td>
<td>velvetleaf</td><td>10G.8C</td><td></td><td>IOC</td>
<td>Seshanifti</td><td>10G.9C</td><td></td><td>10G.9C</td>
<td>Kassie</td><td>10G.8C</td><td></td><td>10G.8C</td>
<td>Baumwoll®</td><td>10G.8C</td><td></td><td>10G.8C</td>
<td>Morning Glory</td><td>10G.9C</td><td></td><td>10G.9C</td>
<td>alfalfa</td><td>10G.8C</td><td></td><td>10G.8C</td>
<td>Weight of datura</td><td>10G.9C</td><td></td><td>IOC</td>
<td>Climbing '</td><td>10G.7C</td><td></td><td>IOC</td>
<td>Corn - !</td><td>10G.9C</td><td></td><td>10G.8C</td>
<td>Finger millet;</td><td>6G</td><td></td><td>10G.4C</td>
<td>Rice.</td><td>10G.6C</td><td></td><td>10G.6C</td>
<td>Cyprus grass</td><td>10G.8C</td><td></td><td>10G.9C</td>
<td>barnyardgrass</td><td>10G.9C</td><td></td><td>10G.9C</td>
<td>wheat</td><td>10G.9C</td><td></td><td>10G.7C</td>
<td>Riesenfuehsschwanz</td><td>10G.9C</td><td></td><td>10G.9C</td>
<td>Wild oats</td><td>10G.7C</td><td></td><td>10G.7C</td>
<td>sorghum</td><td>10G, 8C</td><td></td><td>10G.8C</td>
- 116 No.371668
Table XIV (continued)
<td colspan="6">Soil foliage treatment from above</td>
<td></td><td></td><td>0 II</td><td colspan="2">N-</td><td>/ OCH,</td>
<td></td><td colspan="2">/ Q 2-SO-NH-C-NH- \ li COGH s</td><td>/<sup>_</sup>\</td><td>c N-</td><td>! / ^ CH,</td>
<td>kg / ha</td><td>1/64</td><td colspan="2">1/32</td><td colspan="2">1.16</td>
<td>soybeans</td><td>10G.9C</td><td>10G.9C</td><td></td><td></td><td>10G.8C</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td></td><td></td><td>-</td>
<td>Sesbania</td><td>10G.9C</td><td>10G.9C</td><td></td><td></td><td>10G.9C</td>
<td>Kassie</td><td>10G.9C</td><td>10G.8C</td><td></td><td></td><td>10G.9C</td>
<td>cotton</td><td>10G.7C</td><td>10G.7C</td><td></td><td></td><td>10G.7C</td>
<td>Morning Glory</td><td>10G.9C</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>alfalfa</td><td>10G.9C</td><td>IOC</td><td></td><td></td><td>10G.9C</td>
<td>Weight of datura</td><td>IOC</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>barnacles</td><td>10G.9C</td><td>10G.9C</td><td></td><td></td><td>IOC</td>
<td>Corn</td><td>10G.8C</td><td>10G.7C</td><td></td><td></td><td>10G.9C</td>
<td>crabgrass</td><td>3G</td><td>7G.3C</td><td></td><td></td><td>10G, 5C</td>
<td>rice</td><td>10G.3C</td><td>10G.4C</td><td></td><td></td><td>10G.6C</td>
<td>Cyprus grass</td><td>10G.6C</td><td>10G.6C</td><td></td><td></td><td>10G.8C</td>
<td>barnyardgrass</td><td>10G, 9C</td><td>10G, 7C</td><td></td><td></td><td>10G.9C</td>
<td>wheat</td><td>10G.8C</td><td>10G.7C</td><td></td><td></td><td>10G.9C</td>
<td>Giant foxtail</td><td>10G.7C</td><td>10G.7C</td><td></td><td></td><td>IOC</td>
<td>Wild oats</td><td>10G.7C</td><td>10G.9C</td><td></td><td></td><td>10G.8C</td>
<td>sorghum</td><td>10G.7C</td><td>10G.7C</td><td></td><td></td><td>10G.9C</td>
- 117 No.371668
Table XIV (continued)
<td colspan="4">Soil foliage treatment from above</td>
<td></td><td>IOI / Y</td><td>0 II -so<sub>2</sub>-NH-C-NH- 0 II COCH,</td><td>/<sup>0CH</sup>. <Ö> N- \ OCH,</td>
<td>kg / ha</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>So abjhnen</td><td>10G.9C</td><td>10G.9C</td><td>10G.8C</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Sesbania</td><td>10G.9C</td><td>10G.9C</td><td>10G.9C</td>
<td>Kassie</td><td>10G.8C</td><td>IOC</td><td>10G.9C</td>
<td>cotton</td><td>10G.6C</td><td>10G.6C</td><td>10G.8C</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td>10G, 9C</td>
<td>alfalfa</td><td>10G.9C</td><td>10G.9C</td><td>10G.9C</td>
<td>Weight of datura</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>10G.7C</td><td>10G.8C</td><td>10G.8C</td>
<td>crabgrass</td><td>4G</td><td>5G, 2C</td><td>3G.2C</td>
<td>rice</td><td>10G.4C</td><td>10G.4C</td><td>10G.4C</td>
<td>Cyprus grass</td><td>10G.9C</td><td>10G.9C</td><td>10G, 9C</td>
<td>barnyardgrass</td><td>10G.7C</td><td>10G.9C</td><td>10G.8C</td>
<td>wheat</td><td>8G, 3C</td><td>10G.7C</td><td>10G.8C</td>
<td>Giant foxtail</td><td>10G.9C</td><td>10G.9C</td><td>IOC</td>
<td>Wild oats</td><td>10G.6C</td><td>10G.5C</td><td>8G.4C</td>
<td>sorghum</td><td>10G.8C</td><td>10G.9C</td><td>10G.9C</td>
- 118 No.371668
Table XIV (continued)
<td colspan="4">Soil foliage treatment from above</td>
<td></td><td colspan="3">OCH, / 7S \ Ϊ /<sup>N</sup>Aey / -S0<sub>2</sub> -NH-C-NH- '(JN<sup>x</sup>COCH3 <sup>x</sup>ch3</td>
<td>kg / ha</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>soybeans velvetleaf Sesbania Kassie cotton Morning Glory alfalfa Weight of datura barnacles Corn crabgrass rice Cyprus grass barnyardgrass wheat Giant foxtail Wild oats sorghum</td><td>10G.8C 10G.9C 10G.7C 10G.5C IOC 10G.8C IOC 10G.8C 9G.3C 0 7G 0 8G, 5H 7G.3H 10G, 2C 6G 10G.2C</td><td>10G.8C IOC 10G.9G 10G.9C 10G.8C IOC 10G.9C IOC IOC 10G.8C 3G.2H 10G.2C 4G 10G, 6C 5G 10G.7C 10G.2C 10G.5C</td><td>10G.9C IOC 10G.9C 10G.8C 10G.8C IOC 10G.9C IOC IOC 10G.9C 5G, 2C 10G.4C 2G 10G.7C 5G 10G.4C 10G.3C 10G.5C</td>
- 119
Nr.371668
Table XIV (continued)
<td colspan="4">Soil foliage treatment from above</td>
<td></td><td colspan="3">OCH, <Cj / -S0<sub>2</sub>-NH-C-NH- / 0N<sup>X</sup>(0 N '' COCH, ^ OCH,</td>
<td>kg / ha ~ -</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>soybeans velvetleaf Seshania. Kassie cotton Morning glory · alfalfa Weight of datura barnacles Corn Fingerhiise- rice Cyprus grass' barnyardgrass wheat Giant Fox Swan Wild oats sorghum</td><td>10G.8C 10G.9C 10G.8C 10G, 5C 10G.9C 10G.9C 10G.2C 8G, 4H 0 6G 0 6G.2H 3G, 2H 3G 0 5G, 2H</td><td>10G.8C 10G.9C 10G.8C 10G.9C IOC 8G, 6C IOC 10G.7C 8G, 2C 0 10G.2C 0 9G, 3H 3G 7G 2G 10G.4H</td><td>10G.8G IOC 10G.9C 10G.8C 10G, 8C IOC 10G.6C IOC 10G.9C 9G.4C 2G 10G.3C 5G.2C 10G.5H 3G 10G.3C 3G, 2C 10G.4H</td>
- 120 No.371668
Table XIV (continued)
<td colspan="3">Soil foliage treatment from above</td>
<td></td><td colspan="2">/ 7S \ ° Λλ \ \ U / -SO, -RA-C-NH / u> -OH, \ ll \ COCH, \<sub>H</sub>.</td>
<td>kg / ha</td><td>1.16</td><td>1.4</td>
<td>soybeans velvetleaf Sesbania Kassie cotton Morning Glory alfalfa Weight of datura barnacles Corn crabgrass rice Cyprus grass barnyardgrass wheat Giant foxtail Wild oats sorghum</td><td>10G.8C 5G IOC 10G.8C 5G.2C 4G 2C 4G.2C 3G, 3C 6G, 3H 0 10G.8C 10G.3C 10G.4C 8G 5G 5G 10G.6C</td><td>10G.9C IOC IOC 10G.BC 7G, 3H 9G, 3C 10G.6C 6G, 2C 9G, 6C 10G.7C 2G 10G.7C 10G.3C 10G.5C 10G 8G 8G 10G.6C</td>
- 121 No.371668
Table XIV (continued)
Soil foliage treatment from above
<td></td><td><c</td><td>X \</td><td>p -so<sub>2</sub>-NH-C-NH- COONa</td><td>N-</td><td>/ CH<sub>S</sub>'Xh,</td>
<td>kg / ha</td><td colspan="2">1/32</td><td>1.16</td><td colspan="2">1.4</td>
<td>soybeans</td><td>0</td><td></td><td>0</td><td></td><td>5G, 2C</td>
<td>velvetleaf</td><td>0</td><td></td><td>0</td><td></td><td>5G</td>
<td>Sesbania</td><td>0</td><td></td><td>3G</td><td></td><td>7G</td>
<td>Kassie</td><td>0</td><td></td><td>0</td><td></td><td>5G.3C</td>
<td>cotton</td><td>0</td><td></td><td>0</td><td></td><td>5G</td>
<td>Morning Glory</td><td>0</td><td></td><td>0</td><td></td><td>5G</td>
<td>alfalfa</td><td>0</td><td></td><td>0</td><td></td><td>3G</td>
<td>Weight of datura</td><td>0</td><td></td><td>0</td><td></td><td>2G</td>
<td>barnacles</td><td>0</td><td></td><td>0</td><td></td><td>3G</td>
<td>Corn</td><td>0</td><td></td><td>0</td><td></td><td>8G.SH</td>
<td>crabgrass</td><td>0</td><td></td><td>0</td><td></td><td>0</td>
<td>rice</td><td>0</td><td></td><td>3G</td><td></td><td>8G</td>
<td>Cyprus grass</td><td>0</td><td></td><td>3G</td><td></td><td>8G</td>
<td>barnyardgrass</td><td>0</td><td></td><td>0</td><td></td><td>4G</td>
<td>wheat</td><td>0</td><td></td><td>0</td><td></td><td>4G</td>
<td>Giant foxtail</td><td>0</td><td></td><td>0</td><td></td><td>2G</td>
<td>Wild oats</td><td>0</td><td></td><td>0</td><td></td><td>3G</td>
<td>sorghum</td><td>0</td><td></td><td>4G</td><td></td><td>8G.3H</td>
122
Nr.371668
Table XIV (continued)
<td colspan="5">Soil foliage treatment from above</td>
<td></td><td>CH.O</td><td></td><td colspan="2">0 CO-CH (CH.),</td>
<td></td><td colspan="2">Vv S HC C-NH-C-NH-SO,</td><td>Y _ /</td><td></td>
<td></td><td colspan="2">\ = / οη<sub>3</sub>ο<sup>Ζ</sup>r</td><td colspan="2">w /</td>
<td>kg / ha</td><td>1/32</td><td>1.16</td><td></td><td>1.4</td>
<td>soybeans</td><td>10G.8C</td><td>10G.8C</td><td></td><td>IOC</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td></td><td>IOC</td>
<td>Sesbania</td><td>10G, 9C</td><td>IOC</td><td></td><td>IOC</td>
<td>Kassie</td><td>10G.8C</td><td>10G, 8C</td><td></td><td>10G.9C</td>
<td>cotton</td><td>IOC</td><td>IOC</td><td></td><td>IOC</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td></td><td>IOC</td>
<td>alfalfa</td><td>IOC</td><td>IOC</td><td></td><td>IOC ·</td>
<td>Weight of datura</td><td>IOC</td><td>IOC</td><td></td><td>IOC</td>
<td>barnacles</td><td>IOC</td><td>IOC</td><td></td><td>IOC</td>
<td>Corn</td><td>8G, 3H</td><td>10G.3C</td><td></td><td>10G.8C</td>
<td>crabgrass</td><td>5G</td><td>5G</td><td></td><td>9G, 3C</td>
<td>rice</td><td>10G.6C</td><td>10G.5C</td><td></td><td>10G.6C</td>
<td>Cyprus grass</td><td>10G, 8C</td><td>10G.9C</td><td></td><td>10G.8C</td>
<td>barnyardgrass</td><td>10G.8C</td><td>10G.9C</td><td></td><td>10G.9C</td>
<td>wheat</td><td>8G</td><td>10G</td><td></td><td>10G.3H</td>
<td>Giant foxtail</td><td>10G</td><td>10G</td><td></td><td>10G.3C</td>
<td>Wild oats</td><td>10G</td><td>10G</td><td></td><td>10G.3C</td>
<td>sorghum</td><td>10G, SC</td><td>IOC</td><td></td><td>10G, 8C</td>
- 123 No.371668
Table XIV (continued)
<td colspan="4">Soil foliage treatment from above</td>
<td></td><td></td><td>0 II</td><td></td>
<td></td><td>CH, C></td><td colspan="2">CO-CH (CH,),</td>
<td></td><td>H/</td><td>N f C-NH-C-NH-SO, -</td><td>\ _ - / q \</td>
<td></td><td>/<sup>c =</sup>ch<sub>3</sub></td><td></td><td>w /</td>
<td>kg / ha</td><td>1/32</td><td>1.16</td><td>1.4</td>
<td>soybeans</td><td>10G.8C</td><td>10G.8C</td><td>10G, 8C</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td>-</td>
<td>Sesbanla</td><td>10G.9C</td><td>IOC</td><td>IOC</td>
<td>Kassie</td><td>10G.8C</td><td>10G.8C</td><td>10G.8C</td>
<td>cotton</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>alfalfa</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>10G.9C</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>8G, 3C</td><td>7G, 3C</td><td>10G.9C</td>
<td>crabgrass</td><td>8G</td><td>8G</td><td>10G.3C</td>
<td>rice</td><td>10G.5C</td><td>10G.4C</td><td>10G.6C</td>
<td>Cyprus grass</td><td>10G.8C</td><td>8G.3C</td><td>10G.8C</td>
<td>barnyardgrass</td><td>10G.8C</td><td>10G.6C</td><td>10G.8C</td>
<td>wheat</td><td>9G</td><td>10G.3C</td><td>10G.5C</td>
<td>Giant foxtail</td><td>10G</td><td>10G</td><td>10G.6C</td>
<td>Wild oats</td><td>10G</td><td>10G.3C</td><td>10G.5C</td>
<td>sorghum</td><td>10G.4C</td><td>10G.3C</td><td>10G.8C</td>
- 124 No.371668
Table XIV (continued)
<td colspan="4">Soil foliage treatment from above</td>
<td></td><td>CH.O</td><td colspan="2">0 II CO-CHCCHj)<sub>2</sub>M 0 Y \\ II> ^ \</td>
<td></td><td>N /<sup>C =</sup><sup>CH</sup>j °</td><td>/ C-NH-C-NH-SO<sub>2</sub>- N</td><td>\ Y /</td>
<td>kg / ha</td><td>1/32</td><td>1.16</td><td>1.4</td>
<td>soybeans</td><td>10C.8C</td><td>10G.9C</td><td>10G.8C</td>
<td>velvetleaf</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Seshania</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Kassie</td><td>10G.9C</td><td>10G.9C</td><td>10G, 9C</td>
<td>cotton</td><td>10G.7C</td><td>IOC</td><td>IOC</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>alfalfa</td><td>10G.9C</td><td>IOC</td><td>IOC '</td>
<td>Weight of datura</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>IOC</td><td>-</td><td>IOC</td>
<td>Corn</td><td>-</td><td>8G, SH</td><td>10G.4C</td>
<td>crabgrass</td><td>0</td><td>3G</td><td>7G</td>
<td>rice</td><td>6G</td><td>8G</td><td>10G.4C</td>
<td>Cyprus grass</td><td>10G.8C</td><td>10G.9C</td><td>IOC</td>
<td>barnyardgrass</td><td>7G, 3H</td><td>8G.3H</td><td>8G.3H</td>
<td>wheat</td><td>0</td><td>0</td><td>0</td>
<td>Giant foxtail</td><td>2G</td><td>0</td><td>5G</td>
<td>Wild oats</td><td>5G</td><td>5G</td><td>8G</td>
<td>sorghum</td><td>8G.3H</td><td>10G.3H</td><td>10G.3H</td>
125
Nr.371668
Table XIV (continued)
<td colspan="4">Soil foliage treatment from above</td>
<td></td><td colspan="3">ch<sub>3</sub>O \ f / FÄ hc c-nh-c-nh-so<sub>2</sub>-S ()> z<sup>c == /</sup> /<sup>-</sup>CH, 0 C<sub>2</sub>H<sub>s</sub>-0-C 0</td>
<td>kg / ha</td><td>1/32</td><td>1.16</td><td>1.4</td>
<td>soybeans velvetleaf Sesbania Kassie cotton Morning Glory alfalfa Weight of datura barnacles Corn crabgrass rice Cyprus grass barnyardgrass wheat Giant foxtail Wild oats sorghum</td><td>10G.8C IOC IOC 10G, 9C 10G.9C IOC IOC 10G.9C IOC 10G.9C 5G 10G.7C IOC 10G.BC 8G 7G 10G.6C IOC</td><td>IOC IOC IOC 10G.9C IOC IOC IOC IOC IOC 10G.9C 7G 10G.7C IOC 10G.7C 10G.3C 10G 10G.5C 10G, 8C</td><td>10G.9C IOC 10G.9C 10G.9C IOC IOC IOC IOC IOC IOC 10G.3C 10G.7C IOC 10G.9C 10G.4C 10G, 3C 10G.7C IOC</td>
- 126 No.371668
Table XIV (continued)
<td colspan="4">Soil foliage treatment from above</td>
<td></td><td></td><td>0</td><td></td>
<td></td><td colspan="3"><sup>CH</sup>'° \ C-0 - {- CH) CH \ 0 \ <sup>2 3 3 </sup>nm ,,</td>
<td></td><td colspan="2"></td><td></td>
<td></td><td>/</td><td>\ H</td><td>/ θ \</td>
<td></td><td>HC.</td><td>.C-NH-C-NH-SO.-</td><td>'C i \</td>
<td></td><td colspan="3">n_n \ /</td>
<td></td><td>CH ^</td><td></td><td></td>
<td>kg / ha</td><td>1/32</td><td>1.16</td><td>1.4</td>
<td>soybeans</td><td>10G.3C</td><td>10G.6C</td><td>10G.6C</td>
<td>velvetleaf</td><td>10G.7C</td><td>IOC</td><td>IOC</td>
<td>Sesbania</td><td>10G, 5C</td><td>10G, 7C</td><td>10G.8C</td>
<td>Kassie</td><td>3G</td><td>4G</td><td>8G, 3C</td>
<td>cotton</td><td>10G.4C</td><td>-</td><td>10G.8C</td>
<td>Morning Glory</td><td>10G.3B</td><td>10G, 5B</td><td>10B</td>
<td>alfalfa</td><td>10G.6C</td><td>10G.6C</td><td>10G.9C</td>
<td>Weight of datura</td><td>8G, 3C</td><td>8G.3C</td><td>10G, 6C</td>
<td>barnacles</td><td>10G.4C</td><td>10G.6C</td><td>10G.6C</td>
<td>Corn</td><td>5G, 2H</td><td>8G.3H</td><td>10G, 3H</td>
<td>crabgrass</td><td>0</td><td>0</td><td>0</td>
<td>rice</td><td>8G</td><td>10G.2C</td><td>10G.4C</td>
<td>Cyprus grass</td><td>3G</td><td>8G</td><td>9G</td>
<td>barnyardgrass</td><td>8G, 2C</td><td>10G.3C</td><td>10G.3C</td>
<td>wheat</td><td>0</td><td>3G</td><td>5G</td>
<td>Giant foxtail</td><td>7G</td><td>7G</td><td>10G.3H</td>
<td>Wild oats</td><td>6G</td><td>7G</td><td>9G</td>
<td>sorghum</td><td>5G</td><td>10G.3H</td><td>10G.3H</td>
127 Nr.371668
Table XIV (continued)
<td colspan="3">Soil foliage treatment from above</td>
<td></td><td colspan="2">/<sup>c =</sup>\ ί / <λ \ % / -nh-c-nh-so<sub>2</sub>- / 0 \ / CN ' CiT (CH.) -CH-OC II 0</td>
<td>kg / ha</td><td>1.16</td><td>1.4</td>
<td>soybeans</td><td>10G, 9C</td><td>10G.9C</td>
<td>velvetleaf</td><td>IOC</td><td>-</td>
<td>Sesbania</td><td>IOC</td><td>IOC</td>
<td>Kassie</td><td>IOC</td><td>10G.9C</td>
<td>cotton</td><td>IOC</td><td>IOC</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td>
<td>alfalfa</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>10G.6C</td><td>10G.7C</td>
<td>barnacles</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>10G.2C</td><td>10G.8C</td>
<td>crabgrass</td><td>4G</td><td>7G</td>
<td>rice</td><td>7G</td><td>10G.2C</td>
<td>Cyprus grass</td><td>8G, 3C</td><td>IOC</td>
<td>barnyardgrass</td><td>7G</td><td>10G.3C</td>
<td>wheat</td><td>0</td><td>3G</td>
<td>Giant foxtail</td><td>0</td><td>7G</td>
<td>Wild oats</td><td>3G</td><td>8G</td>
<td>sorghum</td><td>8G.5H</td><td>8G, 2C</td>
- 128 No.371668
Table XIV (continued)
<td>Floor-Bla</td><td>ttwerk treatment from above</td><td></td>
<td></td><td>CH, 0</td><td>0</td>
<td></td><td>0 = N</td><td>ii / ττχ</td>
<td></td><td colspan="2">HC C-NH-C-NH-SO, - () z<sup>N</sup> ) -<sup>z</sup></td>
<td></td><td>ch<sub>3</sub>O<sup>z</sup></td><td>Cl-CH. CH.-OC II 0</td>
<td>kg / ha</td><td>1.16</td><td>1.4</td>
<td>soybeans</td><td>10G.9C</td><td>10G.9C</td>
<td>velvetleaf</td><td>IOC</td><td>-</td>
<td>Sesbania</td><td>10G.9C</td><td>IOC</td>
<td>Kassie</td><td>10G.8C</td><td>IOC</td>
<td>cotton</td><td>10G.8C</td><td>10G.9C</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td>
<td>alfalfa</td><td>10G.9C</td><td>IOC</td>
<td>Weight of datura</td><td>8G, 3C</td><td>10G.5C</td>
<td>barnacles</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>8G.2C</td><td>9G, 2C</td>
<td>crabgrass</td><td>5G</td><td>8G.2C</td>
<td>rice</td><td>10G.4C</td><td>10G.5C</td>
<td>Cyprus grass</td><td>10G.6C</td><td>10G.6C</td>
<td>barnyardgrass</td><td>10G.7C</td><td>10G.8C</td>
<td>wheat</td><td>6G</td><td>10G</td>
<td>Giant foxtail</td><td>10G.7C</td><td>10G, 9C</td>
<td>Wild oats</td><td>8G</td><td>10G.3C</td>
<td>sorghum</td><td>10G</td><td>10G</td>
- 129 No.371668
Table XIV (continued)
<td colspan="2">Ground foliage treatment</td><td colspan="2">from above</td>
<td></td><td>° η<sub>3</sub>ο.</td><td></td><td>Π</td>
<td></td><td></td><td>%</td><td>ii / <~> \</td>
<td></td><td>HC</td><td>C-NK</td><td>-C-NH-SO, - <())</td>
<td></td><td>z<sup>C:</sup></td><td>/ N =</td><td></td>
<td></td><td>ch<sub>3</sub></td><td colspan="2">Cl-CH, CH, -OC<sup>2 2</sup> II 0</td>
<td>kg / ha</td><td>1.16</td><td></td><td>1.4</td>
<td>soybeans</td><td>10G.9C</td><td></td><td>10G.9C</td>
<td>velvetleaf</td><td>-</td><td></td><td>-</td>
<td>Sesbania</td><td>IOC</td><td></td><td>IOC</td>
<td>Kassie</td><td>IOC</td><td></td><td>1QC</td>
<td>cotton</td><td>IOC</td><td></td><td>10G.8C</td>
<td>Morning Glory</td><td>10G.9C</td><td></td><td>10G.9C</td>
<td>alfalfa</td><td>IOC</td><td></td><td>IOC</td>
<td>Weight of datura</td><td>10G.7C</td><td></td><td>10G.8C</td>
<td>barnacles</td><td>-</td><td></td><td>IOC</td>
<td>Corn</td><td>10G, 5C</td><td></td><td>10G, 3C</td>
<td>crabgrass</td><td>4G</td><td></td><td>7G</td>
<td>rice</td><td>10G.4C</td><td></td><td>10G.5C</td>
<td>Cyprus grass</td><td>10G, 8C</td><td></td><td>10G, 5C</td>
<td>barnyardgrass</td><td>10G.8C</td><td></td><td>10G.8C</td>
<td>wheat</td><td>10G</td><td></td><td>10G.4C</td>
<td>Giant foxtail</td><td>10G.3C</td><td></td><td>10G.9C</td>
<td>Wild oats</td><td>10G.2C</td><td></td><td>10G.2C</td>
<td>sorghum</td><td>10G</td><td></td><td>10G.2C</td>
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Table XIV (continued)
<td colspan="3">Soil foliage treatment from above</td>
<td></td><td>CH 0</td><td></td>
<td></td><td><sup>3</sup> \</td><td>0</td>
<td></td><td>/ ~ Λ</td><td><sup>1</sup> / R> \</td>
<td></td><td>N C-NH-</td><td>3-NH-SO, - (()></td>
<td></td><td>\ / C = N</td><td>v © /</td>
<td></td><td colspan="2">CH<sub>3</sub>O 'Cl-CH<sub>2</sub>CH<sub>2</sub>-0-C</td>
<td></td><td></td><td>0</td>
<td>kg / ha</td><td>1.16</td><td>1.4</td>
<td>soybeans</td><td>10G, 9C</td><td>10G, 9C</td>
<td>velvetleaf</td><td>-</td><td>IOC</td>
<td>Sesbania</td><td>IOC</td><td>IOC</td>
<td>Kassie</td><td>10G.9C</td><td>IOC</td>
<td>cotton</td><td>10G.9C</td><td>10G.8C</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td>
<td>alfalfa</td><td>5G</td><td>10G.9C</td>
<td>Weight of datura</td><td>8G, 4C</td><td>10G.4C</td>
<td>barnacles</td><td>IOC</td><td>-</td>
<td>Corn</td><td>5G</td><td>8G, 2C</td>
<td>crabgrass</td><td>3G</td><td>4G</td>
<td>rice</td><td>4G</td><td>6G</td>
<td>Cyprus grass</td><td>10G.4C</td><td>10G.4C</td>
<td>barnyardgrass</td><td>7G</td><td>8G</td>
<td>wheat</td><td>0</td><td>0</td>
<td>Giant foxtail</td><td>0</td><td>0</td>
<td>Wild oats</td><td>0</td><td>5G</td>
<td>sorghum</td><td>6G</td><td>8G</td>
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Table XIV (continued)
<td colspan="3">Soil foliage treatment from above</td>
<td></td><td>CH, 0</td><td></td>
<td></td><td>\ //<sup>C</sup>~ \</td><td>0 II / zx \</td>
<td></td><td colspan="2">N C-NH-C-NH-SO-)</td>
<td></td><td>\ /</td><td></td>
<td></td><td>C = N</td><td>V - ·</td>
<td></td><td>X</td><td></td>
<td></td><td>ch; ci</td><td>ch<sub>2</sub>ch<sub>2</sub>-oo</td>
<td></td><td></td><td>II 0</td>
<td>kg / ha</td><td>1.16</td><td>1.4</td>
<td>soybeans</td><td>10G, 9C</td><td>10G.9C</td>
<td>velvetleaf</td><td>IOC</td><td>-</td>
<td>Sesbania</td><td>IOC</td><td>IOC</td>
<td>Kassie</td><td>10G.9C</td><td>IOC</td>
<td>cotton</td><td>10G.8C</td><td>10G.9C</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td>
<td>alfalfa</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>10G.5C</td><td>10G.8C</td>
<td>barnacles</td><td>IOC</td><td>IOC</td>
<td>Corn</td><td>10G.3H</td><td>10G.3C</td>
<td>crabgrass</td><td>0</td><td>3G</td>
<td>rice</td><td>4G</td><td>7G</td>
<td>Cyprus grass</td><td>5G</td><td>9G.4C</td>
<td>barnyardgrass</td><td>6G</td><td>8G</td>
<td>wheat</td><td>0</td><td>0</td>
<td>Giant foxtail</td><td>0</td><td>3G</td>
<td>Wild oats</td><td>3G</td><td>5G</td>
<td>sorghum</td><td>10G.3H</td><td>10G</td>
- 132 No.371668
Table XIV (continued)
<td colspan="5">Floor-bladder treatment from above</td>
<td colspan="2"></td><td colspan="2">θΗ, Ο s HC C-NH-C-NH-SO <sub>2</sub>- \ / C = N CH ^</td><td>0 II CO-CH \ _</td>
<td colspan="2">kg / ha</td><td>1.16</td><td colspan="2">1.4</td>
<td>soybeans</td><td></td><td>10G.7C</td><td></td><td>10G.8C</td>
<td>velvetleaf</td><td></td><td>IOC</td><td></td><td>IOC</td>
<td>Sesbania</td><td></td><td>IOC</td><td></td><td>IOC</td>
<td>Kassie</td><td></td><td>10G.7C</td><td></td><td>10G.7C</td>
<td>cotton</td><td></td><td>10G.7C</td><td></td><td>10G.9C</td>
<td>Morning Glory</td><td></td><td>10G.9C</td><td></td><td>IOC</td>
<td>alfalfa</td><td></td><td>10G.9C</td><td></td><td>10G.9C</td>
<td>Weight of datura</td><td></td><td>10G.3C</td><td></td><td>10G.6C</td>
<td>barnacles</td><td></td><td>IOC</td><td></td><td>IOC</td>
<td>Corn</td><td></td><td>4G</td><td></td><td>7G, 3H</td>
<td>crabgrass</td><td></td><td>0</td><td></td><td>4G</td>
<td>rice</td><td></td><td>10G.3C</td><td></td><td>10G.3C</td>
<td>Cyprus grass</td><td></td><td>10G, 5C</td><td></td><td>10G.8C</td>
<td>barnyardgrass</td><td></td><td>10G.3H</td><td></td><td>10G.4C</td>
<td>wheat</td><td></td><td>2G</td><td></td><td>7G</td>
<td>Giant foxtail</td><td></td><td>0</td><td></td><td>5G, 2C</td>
<td>Wild oats</td><td></td><td>5G</td><td></td><td>8G, 3H</td>
<td>sorghum</td><td></td><td>10G</td><td></td><td>10G.2C</td>
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Table XIV (continued)
Soil foliage treatment from above
<td></td><td colspan="3">HC C-NH-C-NH-SO, - \ / ? C = N CH,</td><td>-\O/-<sup>a</sup></td>
<td>kg / ha</td><td colspan="2">1.16</td><td colspan="2">1.4</td>
<td>soybeans</td><td>10G.7C</td><td></td><td></td><td>10G.7C</td>
<td>velvetleaf</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>Sesbania</td><td>10G.7C</td><td></td><td></td><td>10G, 9C</td>
<td>Kassie</td><td>10G.7C</td><td></td><td></td><td>10G.7C</td>
<td>cotton</td><td>10G.6C</td><td></td><td></td><td>10G.9C</td>
<td>Morning Glory</td><td>IOC</td><td></td><td></td><td>IOC</td>
<td>alfalfa</td><td>10G.9C</td><td></td><td></td><td>10G.9C</td>
<td>Weight of datura</td><td>10G.8C</td><td></td><td></td><td>10G.8C</td>
<td>barnacles</td><td>IOC</td><td></td><td></td><td>10G.9C</td>
<td>Corn</td><td>10G.5H</td><td></td><td></td><td>8G</td>
<td>crabgrass</td><td>0</td><td></td><td></td><td>5G</td>
<td>rice</td><td>8G, 2C</td><td></td><td></td><td>10G.6C</td>
<td>Cyprus grass</td><td>7G.2C</td><td></td><td></td><td>7G.3C</td>
<td>barnyardgrass</td><td>8G.3C</td><td></td><td></td><td>10G, 6C</td>
<td>wheat</td><td>4G</td><td></td><td></td><td>8G</td>
<td>Giant foxtail</td><td>2G</td><td></td><td></td><td>6G</td>
<td>Wild oats</td><td>10G</td><td></td><td></td><td>8G.3C</td>
<td>sorghum</td><td>10G</td><td></td><td></td><td>10G</td>
Test D
The high herbicidal activity of one of the compounds of the formula (I) is evident from the results of this test. The experiment concerned the application to the soil before sprouting. 5 plastic containers 25 cm in diameter were used which were filled with Falsington slurry clay. A set of pots were planted with weeds whose seeds were uniformly mixed with 1.2 cm of the top soil layer. The following species were selected: Johnsongrass (Sorghum halepense), Barnyardgrass (Echinochloa crusgalli), Finger-millet (Digitaria sanguinalis), Giant foxtail (Setaria faberii), Common hellebore (Abutilon theophrasti), common. Datura (Datura 10 stramonium), mustard (Brassica arvensis) and goosefoot (Amaranthus retroflexus). Another set of pots were planted with the following crops at one to four species per pot (corn at a depth of 3.7 cm), cotton, soybeans, sunflowers, Clinton oats, wheat, Black Valentine beans, rice, sorghum Peas, flax and peanuts (all 2.5 cm deep), cucumbers, cabbage, alfalfa, wild saffron, sugar beets, tomatoes, spinach, barley and Kentucky cattle grass (all 15 1.2 cm deep). Immediately after planting, the test chemical, dissolved in a non-phytotoxic solvent, was applied to the soil surface. Ever. one weed-containing pot and one pot containing each of the plants was left untreated for comparison. The treated and untreated pots were immediately watered with simulation of 4 mm of rain and then kept in the greenhouse for a few weeks. The visual response of weeds and crops was evaluated 28 days after treatment following the system described above for Test A. The data are given in Table XV.
Table XV
<img file="AT371668B_D0068.tif" />
- 135 No.371668
Test E
This greenhouse test illustrates the utility of certain compounds of formula (I) for controlling broadleaf weed species and Cyprus grass in young wheat and barley crops. Plastic pots 25 cm in diameter filled with fertilized 5 and limed Fallsington sludge clay were used. The following weed species were planted twice in a soldering interval: mustard (Brassica arvensis), burdock (Xanthium spp.), Morning glory (Ipomoea hederacea), cassia (Cassia tora), common wort (Abutilon theophrasti), alfalfa (as indicator species) , Kochia (Kochia scoparia), Sesbania (Sesbania exaltata), Russian thistle (Salsola kali), Datura stramonium, and Cyprus grass (Cyperus rotundus). In addition, 10 wheat and barley were planted in separate plastic pots filled with the same soil only at the time of the first planting. All plantings were treated with the test chemical dissolved in a non-phytotoxic solvent immediately after completion of the second planting session. At this time, the wheat was about 15 to 17.5 cm high and the barley was 12.5 to 15 cm high and both were in the two-leaf growth stage. The weed species with the earlier planting date were 2.5 to 12.5 cm high. The application levels were 0.004, 0.007, 0.015 and 0.030 kg / ha for weeds and 0.12, 0.25 and 0.50 kg / ha for wheat and barley. The post-sprouting portion of this test was visually assessed for plant response 21 days after treatment, and the pre-sprouted portion 28 days post-treatment. The evaluation system described for test method A was used. The results are summarized in Table XVI.
Table XVI
<td colspan="5">Before sprouting on Fallsington mud clay</td>
<td></td><td colspan="4">/ OCH, \ O / -so<sub>2</sub>-nh-c-nh- / o \ -X NX Xoo- ^ och<sub>3</sub></td>
<td>kg / ha</td><td>1/256</td><td>1/128</td><td>1/64</td><td>1/32</td>
<td>mustard barnacles Morning Glory Kassie velvetleaf alfalfa Sesbania Kochia Soot. thistle Weight of datura Cyprus grass</td><td>9G.9C 7G, 7H 8G, 7C 8G.5C 8G.3H 5G 7G, 3C 9G, 9C 5G 7G, 2C 7G</td><td>10C 8G, 8H 8G, 7C 8G, 5C 8G.3H 5G, 2C 8G.9C 10C 7C 8G.7C 8G</td><td>10C 8G, 8H 8G, 7C 8G, 5C 8G, 5H 5G 8G.9C 10C 7C 8G, 9C 9G</td><td>10C 8G, 9H 8G, 9C 8G, 8C 9G, 5H 8G, 7C 9G, 9C 10C 9C 8G.9C 10E</td>
- 136 No.371668
Table XVI (continued)
<td colspan="5">Before sprouting on Fallsington mud clay</td>
<td></td><td colspan="4">/ CH \ O / -SO, -NH-C-NH- / Q \<sup>λ</sup><N- ^ COO- / '' OCH,</td>
<td>kg / ha</td><td>1/256</td><td>1/128</td><td>1/64</td><td>1/32</td>
<td>mustard barnacles Morning Glory Kassie velvetleaf alfalfa Sesbania Kochia Soot. thistle Weight of datura Cyprus grass</td><td>IOC 8G.8C 8G.6C 8G.5C 9G.8C 7G 7G, 3C 9G.9C 7C 7G.6C 6G.3C</td><td>IOC 8G.8H 9G.9C 8G.5C 9G.9C 7G.2C 7G.5C IOC 8C 7G.5C 7G, 2C</td><td>IOC 8G.8H IOC 8G, 9C IOC 9G.8C 8G, 8C IOC IOC 8G.9C 8G</td><td>IOC 8G, 9H IOC 8G.8C IOC 9G, 7C IOC IOC IOC 8G, 7C 8G</td>
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Table XVI (continued)
<td colspan="5">After the .Sprießen</td>
<td></td><td><O></td><td>0 II -so<sub>2</sub>NH-c-<sup>k</sup>COO /</td><td colspan="2">OCH,<sup>NB</sup>- <0 /<sup>x</sup> OCH,</td>
<td>kg / ha</td><td>1/256</td><td>1/128</td><td>1/64</td><td>1/32</td>
<td>mustard</td><td></td><td></td><td></td><td></td>
<td>barnacles</td><td>IOC</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Morning Glory</td><td>IOC</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Kassie</td><td>9C</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>velvetleaf</td><td>-</td><td>IOC</td><td>IOC</td><td>-</td>
<td>alfalfa</td><td>5G</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Sesbania</td><td>IOC</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Kochia</td><td>-</td><td>-</td><td>IOC</td><td>-</td>
<td>Soot. thistle</td><td>8C</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Weight of datura</td><td>7G, 5C</td><td>10G.5C</td><td>10G.7C</td><td>10G.6C</td>
<td>Cyprus grass</td><td>7G, 3C</td><td>10G, 8C</td><td>10G, 5C</td><td>10G</td>
<td colspan="5"></td>
<td>kg / ha</td><td>1.8</td><td>1.4</td><td>1.2</td><td></td>
<td>wheat</td><td>2G</td><td>2G, 2C</td><td>6G, 3C</td><td></td>
<td>barley</td><td>0</td><td>6G.2C</td><td>8G, 3C</td><td></td>
- 138 Nr.371688
Table XVI (continued)
<td colspan="5">After sprouting</td>
<td></td><td colspan="4">/ CH<sub>S</sub>¢ 0 / -SOj-NH-C-NH- / Q \ -Υ <sup>N</sup>-Y<sup>x</sup>coo- / ych<sub>3</sub></td>
<td>kg / ha</td><td>1/256</td><td>1/128</td><td>1/64</td><td>1/32</td>
<td>mustard barnacles Morning Glory Kassie Grieswnrz alfalfa Sesbania Kochia Soot. thistle Weight of datura Cyprus grass</td><td>IOC IOC IOC 10C 10C IOC 10C 10G.4C 3G</td><td>IOC 10C 9C IOC 10C IOC IOC 10G.8C 5G, 3C</td><td>IOC IOC 10C 10C 10C IOC IOC 10G.8C 10G.7C</td><td>IOC IOC IOC 10C 10C 10C 10G.9C 10C</td>
<td colspan="5"></td>
<td>kg / ha</td><td>1.8</td><td>1.4</td><td>1.2</td><td></td>
<td>wheat barley</td><td>0 5G</td><td>0 5G, 2C</td><td>5G, 3C 7G, 3C</td><td></td>
Test F
Several compounds of formula (I) are highly effective against Cyprus grass, as shown by the following test.
Cypress grass collen (Cyperus rotundus) was planted at about 2 cm depth in 10 cm diameter plastic pots containing Fallington mud clay. The test compounds, dissolved in a non-phytotoxic solvent, were applied in a volume of 560 l / ha by four different methods, namely spraying on the ground, spraying on tubers / soil, incorporation into the soil and spraying after sprouting. When spraying the soil were the verbin<sup>10</sup> fertilize on the pressed soil surface immediately after planting sprayed on. In tubers / soil spraying, the compounds were sprayed onto the exposed tubers and attached soil before covering with untreated soil. When incorporated into the soil, the agent was mixed with the covering soil. In the treatment after sprouting, the Cyprus grass leaves and the surrounding soil surface were sprayed after the Cyprus grass had risen and reached a height of about 12 cm.
Immediately after spraying the surface, tubers and soil and placing in the soil, the plantings were moistened with about 0.3 cm of water over 90 minutes and then brought into the greenhouse. The plants treated after sprouting were placed directly in the greenhouse and poured gently so that the agent was not washed off the leaves.
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Table XVII below gives the results 4 weeks after the treatment of Cyprus grass with the tested compounds.
Table XVII
Cyprus grass test
<td></td><td>CH, ^ / CH</td><td>Μ O ii χ-NH-C -N</td><td colspan="2">NH-SO, - \ o / ch<sub>3</sub>II 0</td>
<td></td><td colspan="4">Rating after 4 weeks</td>
<td></td><td>Ground-</td><td>tuber</td><td>ground</td><td></td>
<td>kg / ha</td><td>surface</td><td>sprayed</td><td>incorporated</td><td>after sprouting</td>
<td>0,004</td><td>8E, 9G</td><td>10E</td><td>10E</td><td>4C, 7G</td>
<td>0,008</td><td>10E</td><td>10E</td><td>10E</td><td>9C</td>
<td>0.016</td><td>10E</td><td>10E</td><td>10E</td><td>9C</td>
<td>0.032</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td>0.064</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
Cyprus grass test
<td></td><td><Q</td><td colspan="3">och<sub>3</sub>θ / \ II ΛΑ \ /-SO<sub>2</sub>-NH-C-NH-γ) 2 COCH, \<sub>0H</sub>_</td>
<td></td><td colspan="4">Rating after 4 weeks</td>
<td></td><td>Ground-</td><td>tuber</td><td>ground</td><td></td>
<td>kg / ha</td><td>surface</td><td>sprayed</td><td>incorporated</td><td>after sprouting</td>
<td>0,004</td><td>8E, 9G</td><td>10E</td><td>10E</td><td>5C.7G</td>
<td>0,008</td><td>10E</td><td>10E</td><td>10E</td><td>9C</td>
<td>0.016</td><td>10E</td><td>10E</td><td>10E</td><td>9C</td>
<td>0.032</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td>0.064</td><td>10E</td><td>10Ξ</td><td>10E</td><td>IOC</td>
- 140
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Table XVII (continued). Cyprus grass test
<td></td><td colspan="2">_ 0 / R> \ <sup>11</sup>/ -<sup>S0</sup>2 -NH-C-NH - \ ii<sup>x</sup>coch<sub>3</sub></td><td colspan="2"><sub>z</sub>ogh<sub>3</sub>z N-<sup>z</sup>- <O> N<sup>x</sup>och<sub>3</sub></td>
<td></td><td colspan="4">Rating after 4 weeks</td>
<td>kg / ha</td><td>Ground- surface</td><td>tuber sprayed</td><td>ground incorporated</td><td>after sprouting</td>
<td>0,004</td><td>9E.9G</td><td>8E, 9G</td><td>8E, 9G</td><td>8C</td>
<td>0,008</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td>0.016</td><td>10E</td><td>10E</td><td>10E</td><td>10C</td>
<td>0.032</td><td>10E</td><td>10E</td><td>10E</td><td>9C</td>
<td>0.064</td><td>10E</td><td>10E</td><td>10E</td><td>IOC</td>
Cyprus grass test
<td></td><td><O></td><td>0 II -SO<sub>2</sub>-NH-C-NH- 0 \ ll COCH,</td><td colspan="2">.och<sub>3</sub>N- y - <0 / \ C "</td>
<td></td><td colspan="4">Rating after 4 weeks</td>
<td></td><td>Ground-</td><td>tuber</td><td>ground</td><td></td>
<td>kg / ha</td><td>surface</td><td>sprayed</td><td>incorporated</td><td>after sprouting</td>
<td>0,004</td><td>4C, 7G</td><td>5C, 8G</td><td>5C, 8G</td><td>0</td>
<td>0,008</td><td>4C, 7G</td><td>5C, 8G</td><td>5C, 8G</td><td>2G</td>
<td>0.016</td><td>4C.7G</td><td>5C.9G</td><td>5C.8G</td><td>2G</td>
<td>0.032</td><td>5C.8G</td><td>5G, 9G</td><td>5C.9G</td><td>2C.5G</td>
<td>0.064</td><td>5C, 8G</td><td>5C.9G</td><td>6C.9G</td><td>5C, 7G</td>
- 141 No.371668
Table XVII (continued)
Cyprus grass test
<td></td><td><C</td><td colspan="2">_ 0 λ \ <sup>11</sup>J) -so, -nh-c-nh _ (0 \ ii<sup>X</sup>COCH,</td><td colspan="2">OCH, N ~ \ - (0> Xoch,</td>
<td></td><td></td><td></td><td>rating</td><td>after 4 weeks</td><td></td>
<td></td><td>Ground-</td><td></td><td>tuber</td><td>ground</td><td></td>
<td>kg / ha</td><td>surface</td><td></td><td>sprayed</td><td>incorporated</td><td>after sprouting</td>
<td>0,004</td><td>3C.6G</td><td></td><td>3C, 7G</td><td>3C, 7G</td><td>0</td>
<td>0,008</td><td>4C.8G</td><td></td><td>4C, 8G</td><td>4C.8G</td><td>0</td>
<td>0.016</td><td>-</td><td></td><td>4C, 8G</td><td>4C.8G</td><td>2C, 3G</td>
<td>0.032</td><td>4C.8G</td><td></td><td>4C.8G</td><td>4C.8G</td><td>3G</td>
<td>0.064</td><td>5C, 8G</td><td></td><td>-</td><td>4C, 8G</td><td>3C, 4G</td>
- 142 No.371668
Table XVII (continued) • Cyprus grass test
<td colspan="5">(O / - so, "- '<sup>1</sup>»- (0 / - \ 0 <sub>N</sub>coch<sub>3</sub></td>
<td rowspan="2">kg / ha</td><td colspan="4">Rating after 4 weeks</td>
<td>Ground- surface</td><td>tuber sprayed</td><td>ground incorporated</td><td>after sprouting</td>
<td>0.032 0,125 0.5</td><td>0 2E, 7G 10E</td><td>2G 4E, 8G 10E</td><td>0 8E, 9G 10E</td><td>0 9C 10E</td>
<td colspan="5">0 / - \ II <sup>N</sup>-<sup>N</sup>\ O / - <sup>S</sup>°<sup>2</sup> -<sup>NH</sup>'<sup>C</sup>-<sup>NH</sup>- \ 0 / -<sup>CH</sup>3 "\ Ίί <sup>N</sup>~ \<sup>C0CH</sup>3 ^ CH<sub>3</sub></td>
<td>0.032 0,125 0.5</td><td>2G 10E 10E</td><td>2G 4E, 8G 10E</td><td>3G 8E, 8G 10E</td><td>0 9C IOC</td>
- 143
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Table XVII (continued)
Cyprus grass test
<td colspan="5">ch<sub>3</sub>O HC / C-NH-C-NH-SOa-ς ' \ = N \ ' ch<sub>3</sub>c / c<sub>2</sub>H<sub>s</sub>-oo 0</td>
<td rowspan="2">kg / ha</td><td colspan="4">Rating after 4 weeks</td>
<td>Ground- surface</td><td>tuber sprayed</td><td>ground incorporated</td><td>after sprouting</td>
<td>0,008 0.032 0,125 0.25</td><td>10E 10E 10E 10E</td><td>10E 10E 10E 10E</td><td>10E 10E 10E 10E</td><td>IOC IOC IOC IOC</td>
<td colspan="5">0 II ch<sub>3</sub>o co- (ch<sub>2</sub>)<sub>3</sub> ch<sub>3</sub>/<sup>c =</sup>\ / <S \ HC .C-NH-C-NH-SO, - / f J / / CH,</td>
<td>0,008 0.032 0,125 0.5</td><td>2C, 4G 3C, 6G 2C, 8G 2C, 8G</td><td>3C.7G 3C, 7G 3C, 8G 5E.9G</td><td>3C, 8G 3C.7G 5E, 9G 5E.9G</td><td>5C.7G 3C.6G 8C 5C, 6G</td>
- 144 No.371668
Table XVII (continued)
Cyprus grass test
<td colspan="5">0 II CH, 0 CO-CH (CH<sub>3</sub>)<sub>2</sub>, C-N. j? ) -v N<sup>Z</sup> ^ C-NH-O-NH-SOJ \ o / V = N<sup>Z</sup>CH<sub>S</sub>O<sup>Z</sup></td>
<td rowspan="2">kg / ha</td><td colspan="4">Rating after 4 weeks</td>
<td>Ground- surface</td><td>tuber sprayed</td><td>ground incorporated</td><td>after sprouting</td>
<td>0,004 0,008 0.016 0.032</td><td>8G 8G 8E.9G 5E, 9G</td><td>7G 8G 6E.9G 8E, 9G</td><td>8G 8G 8E, 9G 10E</td><td>8C 9C 9C 10C</td>
<td colspan="5">0 II CH 0 CO-CHCCH,), 3 XK 3 2 f / ta hc <sup>x</sup>C-NH-C-NH-so<sub>2</sub>-S f J) \ N =<sup>Z</sup> '-'<sup>GH</sup>3</td>
<td>0,008 0.032 0,125 0.25</td><td>10E 10E 10E 10E</td><td>10E 10E 10E 10E</td><td>9E, 9G 10E 10E 10E</td><td>10C IOC IOC IOC</td>
- 145 No.371668
Table XVII (continued)
Cyprus grass test
<td colspan="5">0 II CH n CO-CH (CH) \ 0 \ HC AnH-C-NH-SO<sub>2</sub>- (Q) 'c = N' - '<sup>ch</sup>3 °<sup>Z</sup></td>
<td rowspan="2">kg / ha</td><td colspan="4">Rating after 4 weeks</td>
<td>Ground- surface</td><td>tuber sprayed</td><td>ground incorporated</td><td>after sprouting</td>
<td>0,008 0.032 0,125 0.25</td><td>10E 10E 10E 10E</td><td>10E 10E 10E 10E</td><td>10E 10E 10E 10E</td><td>10C IOC IOC IOC</td>
<td colspan="5">0 II ch<sub>3</sub>o c- ° -ch<sub>3</sub>.C - N<sub>K</sub> f? ) -. '1 / o \ N / C-NH-C-NH-SO, - <\ -ci ^ C = N<sup>Z</sup> '- / ch<sub>3</sub>O</td>
<td>0,008 0.032 0,125</td><td>3G 7G 9G</td><td>4G 7G 9G</td><td>5G 7G 9G</td><td>3G 5C.6G IOC</td>
- 146 No.371668
Table XVII (continued) • Cyprus grass test
<td colspan="5">0 II CH<sub>S</sub>OC ^ O-CH<sub>3</sub>/ "Λ f / f; \ HC / C-NH-C-NH-SO.Q QJ J-Cl ^ C = N \ ' CH,</td>
<td rowspan="2">kg / ha</td><td colspan="4">Rating after 4 weeks</td>
<td>Ground- surface</td><td>tuber sprayed</td><td>ground incorporated</td><td>after sprouting</td>
<td>0,008 0.032 0,125</td><td>2C, 5G 9G 10E</td><td>7G 10E 10E</td><td>7G 8E.9G 10E</td><td>2C.5G 9C 9C</td>
<td colspan="5">0 II CH<sub>3</sub>O <sup>C</sup>\ ° <sup>CH</sup>3 HC / C-NH-C-NH-SO <sub>2</sub>-ί Q_J> -Cl \ = N '-' H<sub>3</sub> co<sup>z</sup></td>
<td>0,008 0.032 0,125</td><td>8E, 9C 10E 10E</td><td>10E 10E 10E</td><td>10E 10E 10E</td><td>10C 10C 10C</td>
Test G
Purple cypress grass corms (Cyperus rotundus, L.) were planted at about 2 cm depth in Fallsington mud (about 1% organic material) from Delaware and in flanagane clay (about 5% organic matter) from Illionois. Five tubers were planted in plastic pots, each 10 cm in diameter. The treatments listed in Table XVII were performed in three different ways, namely spraying the soil surface, spraying tubers and soil and incorporating it into the soil. In the soil spraying, the material was sprayed after planting on the pressed ground, but before the sprouting of the Cyprus grass. In the 10 tubers / soil spray, the material was sprayed on the exposed tubers and attached soil before the tubers were covered with untreated soil. When bringing in the
Earth, the material was mixed with the covering earth.
Immediately after the treatment, the treated pots were moistened with about 0.3 cm of water over 90 minutes and placed in the greenhouse. The high efficiency of these compounds in Cyprus grass is reflected in the evaluations after 4 weeks, as shown in Table XVIII.
147 Nr.371668
Table XVIII
<img file="AT371668B_D0069.tif" />
<td rowspan="3">kg / ha</td><td colspan="6">Rating of Cyprus grass after 4 weeks</td>
<td colspan="2">Surface spray</td><td colspan="2">Tubers / ground spraying</td><td colspan="2">Incorporation into soil</td>
<td>A</td><td>B</td><td>A</td><td>B</td><td>A</td><td>B</td>
<td>0,008</td><td>10E</td><td>4C, 7G</td><td>10E</td><td>7E, 9G</td><td>10E</td><td>9E, 9G</td>
<td>0.016</td><td>10E</td><td>8E, 8G</td><td>10E</td><td>10E</td><td>10E</td><td>8E, 9G</td>
<td>0.032</td><td>10E</td><td>9E, 9G</td><td>10E</td><td>10E</td><td>10E</td><td>10E</td>
<td></td><td></td><td>O</td><td></td><td></td><td></td><td></td>
<td></td><td></td><td>II</td><td></td><td></td><td></td><td></td>
<td></td><td></td><td>X '</td><td rowspan="2">OCH, O II 3O<sub>2</sub>NHCNH-</td><td colspan="2">OCH, N <</td><td></td>
<td></td><td></td><td><O> -</td><td>(O> M /</td><td></td><td></td>
<td></td><td></td><td></td><td></td><td colspan="2">^ OCH,</td><td></td>
<td>0,008</td><td>5C, 8G</td><td>0</td><td>9E.9G</td><td>5E, 7G</td><td>8E, 9C</td><td>2C, 3G</td>
<td>0.016</td><td>9E, 9G</td><td>2C, 4G</td><td>10E</td><td>10E</td><td>9E, 9C</td><td>3C.3G</td>
<td>0.032</td><td>10E</td><td>10C</td><td>10E</td><td>9E.10C</td><td>10C</td><td>7E.3C.8G</td>
A = about 1% organic material B = about 4% organic material
Test H
Plastic trays 25 cm in diameter, lined with polyethylene, were filled with prepared Fallsington sludge lees. The one trough was made with seeds of wheat 5 (Triticum aestivum), barley (Hordeum vulgare), wild oats, Avena fatua, fluffy trespe, Bromus tectorum, dry tresps, Bromus secalinus, black grass, Alopecurus myosuroides, annual cattle grass, Poa annua, green foxtail , Setaria viridis, field shrub, Agropyron repens, Italian ryegrass / Lolium multiflorum and Bromus rigidus. The other trough was made with seeds of curled knotweed, Polygonum convolvulus, Kochia scoparia, Knotweed, Polygonum 10 pennsylvanicum, False chamomile, Matricaria inodora, Jimhill mustard, Sisymbrium altissium, Wild mustard, Brassica kaber, Descurainia pinnata, Goosefoot, Amaranthus retroflexus and Russicher Thistle, Salsola kali planted. The two troughs were treated before sprouting. At the same time, two troughs in which the same plants grew were treated after sprouting. At the time of treatment, the height of the plants was 1 to 15 cm, depending on the species.
The test compounds were diluted with a non-phytotoxic solvent and sprayed from above over the troughs. Untreated and solvent-alone treated controls were used for comparison. All treated slides were kept in the greenhouse for 20 days and then compared to controls by visual assessment. The results are given in Table XIX. Again, the potential utility of certain test compounds for weed control in wheat and barley is evident.
- 148
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Table XIX
<td>CH,</td><td></td><td></td>
<td colspan="2">\ -N 0</td><td></td>
<td></td><td>\ II / - \</td><td></td>
<td colspan="2">/ -NH-C-NH-S0<sub>2</sub> - / Q</td><td>\</td>
<td>CH,</td><td>ΟΗ, ΟΟ ^</td><td></td>
<td></td><td>II</td><td></td>
<td></td><td>0</td><td></td>
<td>kg / ha</td><td>1.16</td><td>1.8</td>
<td>Before sprouting</td><td></td><td></td>
<td>wheat</td><td>9F, 9G</td><td>9E, 9G</td>
<td>barley</td><td>7H, 8G</td><td>8H.8G</td>
<td>Wild oats</td><td>4H.7G</td><td>7H.8G</td>
<td>brome</td><td>9E.9G</td><td>10E</td>
<td>Trockentrespe</td><td>7G.8G</td><td>9E.9G</td>
<td>Black grass</td><td>SH.8G</td><td>8H, 9G</td>
<td>einjähr. cattle grass</td><td>5C.7G</td><td>7C, 8G</td>
<td>gr. Foxtail</td><td>8C.8G</td><td>8C, 9G</td>
<td>quackgrass</td><td>5H.7G</td><td>7H, 8G</td>
<td>ital.Raigras</td><td>6H, 7G</td><td>8H.8G</td>
<td>Bromusrigidus</td><td>8C, 9G</td><td>IOC</td>
<td>wild knotweed</td><td>4C.7G</td><td>5C.8G</td>
<td>Kochia</td><td>9C, 9G</td><td>9C, 9G</td>
<td>knotweed</td><td>7C, 8G</td><td>9C, 9G</td>
<td>wrong camomile</td><td>9C, 9G</td><td>9C.9G</td>
<td>Jimhill mustard</td><td>IOC</td><td>IOC</td>
<td>Wild mustard</td><td>8C, 8G</td><td>9C, 9G</td>
<td>D.pinnata</td><td>IOC</td><td>IOC</td>
<td>goosefoot</td><td>8C.9G</td><td>IOC</td>
<td>Soot. thistle</td><td>7C.7G</td><td>8C.8G</td>
- 149
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Table XIX (continued)
<td>CH,</td><td></td><td></td>
<td>\ _</td><td>0</td><td></td>
<td></td><td>\ II / zX</td><td>\</td>
<td><Q Ο) /</td><td>/ -NH-C-NH-so<sub>2</sub>-</td><td>/</td>
<td></td><td>CH OC<sup>9</sup> II</td><td></td>
<td></td><td>II 0</td><td></td>
<td>kg / ha</td><td>1.16</td><td>1.8</td>
<td>Before sprouting</td><td></td><td></td>
<td>wheat</td><td>9C</td><td>IOC</td>
<td>barley</td><td>9C</td><td>IOC</td>
<td>Wild oats</td><td>9C</td><td>IOC</td>
<td>brome</td><td>IOC</td><td>IOC</td>
<td>Trockentrespe</td><td>IOC</td><td>IOC</td>
<td>Black grass</td><td>IOC</td><td>IOC</td>
<td>einjähr. cattle grass</td><td>IOC</td><td>IOC</td>
<td>gr. Foxtail</td><td>IOC</td><td>IOC</td>
<td>quackgrass</td><td>IOC</td><td>IOC</td>
<td>Italian ryegrass</td><td>IOC</td><td>IOC</td>
<td>Bromusrigidus</td><td>IOC</td><td>IOC</td>
<td>wild knotweed</td><td>IOC</td><td>IOC</td>
<td>Kochia</td><td>IOC</td><td>IOC</td>
<td>knotweed</td><td>IOC</td><td>IOC</td>
<td>wrong camomile</td><td>IOC</td><td>IOC</td>
<td>Jimhill mustard</td><td>IOC</td><td>IOC</td>
<td>Wild mustard</td><td>IOC</td><td>IOC</td>
<td>D. pinnata</td><td>IOC</td><td>IOC</td>
<td>Gäsefuß</td><td>IOC</td><td>IOC</td>
<td>Soot. thistle</td><td>IOC</td><td>IOC</td>
- 150 No.371668
Table XIX (continued)
<td colspan="2">ch<sub>3</sub>O \ ii N C-NH-C-NH-SO, - \ / C = N ch<sub>3</sub>O<sup>z</sup></td><td>0 II CO-CH (CH<sub>3</sub>), \ - <O></td><td></td>
<td>kg / ha</td><td>1/64</td><td>1 / 3Z</td><td>1.16</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>wheat</td><td>0</td><td>0</td><td>0</td>
<td>barley</td><td>0</td><td>0</td><td>0</td>
<td>Wild oats</td><td>0</td><td>0</td><td>0</td>
<td>brome</td><td>0</td><td>0</td><td>IG</td>
<td>Trockentrespe</td><td>0</td><td>0</td><td>IG</td>
<td>Sehwarzgras</td><td>0</td><td>0</td><td>2G</td>
<td>einjähr. cattle grass</td><td>0</td><td>0</td><td>IG</td>
<td>gr. Foxtail</td><td>0</td><td>0</td><td>IG</td>
<td>quackgrass</td><td>0</td><td>0</td><td>0</td>
<td>Italian ryegrass</td><td>0</td><td>0</td><td>0</td>
<td>Bromusrigidus</td><td>0</td><td>0</td><td>0</td>
<td>wild knotweed</td><td>3C.5G</td><td>7C.8G</td><td>7C.8G</td>
<td>Kochia</td><td>5C, 7G</td><td>7C, 8G</td><td>9C</td>
<td>knotweed</td><td>4C, 7G</td><td>IOC</td><td>IOC</td>
<td>wrong camomile</td><td>9G</td><td>9G</td><td>9G</td>
<td>Jimhill mustard</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Wild mustard</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>D. pinnata</td><td>7C, 9G</td><td>IOC</td><td>IOC</td>
<td>goosefoot</td><td>7G</td><td>5C, 8G</td><td>IOC</td>
<td>Soot. thistle</td><td>3G</td><td>4G</td><td>7C, 5G</td>
- 151 No.371668
Table XIX (continued)
<td></td><td></td><td>0</td><td></td>
<td>CHO</td><td></td><td>CO-CH (CH)</td><td></td>
<td>V</td><td>.. θ</td><td></td><td></td>
<td>, c-</td><td>- N ti</td><td></td><td></td>
<td>//</td><td>II</td><td></td><td></td>
<td>N</td><td colspan="2">C-NH-C-NH-SO .- (</td><td></td>
<td></td><td>/ N =</td><td>'\ ϊί /</td><td></td>
<td>/</td><td></td><td></td><td></td>
<td><sup>CH</sup>3 °</td><td></td><td></td><td></td>
<td>kg / ha</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>Before sprouting</td><td></td><td></td><td></td>
<td>wheat</td><td>0</td><td>0</td><td>IC</td>
<td>barley</td><td>0</td><td>0</td><td>0</td>
<td>Wild oats</td><td>0</td><td>0</td><td>IC</td>
<td>brome</td><td>0</td><td>0</td><td>0</td>
<td>Trockentrespe</td><td>0</td><td>0</td><td>0</td>
<td>Black grass</td><td>0</td><td>0</td><td>0</td>
<td>ein3ähr. cattle grass</td><td>0</td><td>0</td><td>2G</td>
<td>gr. Foxtail</td><td>IC</td><td>IC</td><td>2C.3G</td>
<td>quackgrass</td><td>0</td><td>0</td><td>0</td>
<td>Italian ryegrass</td><td>0</td><td>0</td><td>0</td>
<td>Bromusrigidus</td><td>0</td><td>0</td><td>0</td>
<td>wild knotweed</td><td>9C</td><td>IOC</td><td>IOC</td>
<td>Kochia</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>knotweed</td><td>9C</td><td>9C</td><td>IOC</td>
<td>wrong camomile</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Jimhill mustard</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>Wild mustard</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>D. pin ata</td><td>IOC</td><td>IOC</td><td>IOC</td>
<td>goosefoot</td><td>9C</td><td>IOC</td><td>IOC</td>
<td>Soot. thistle</td><td>9C</td><td>IOC</td><td>IOC</td>
- 152 No.371668
Table XIX (continued)
<td colspan="4">.CH, _ 0 M / / / Ύ \ N / <Ύ <QJ) -so<sub>2</sub>-nh-c-nh- / Qj N -YN-Y<sup>x</sup>coo- / YqcHj</td>
<td>kg / ha</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>Before sprouting wheat barley Wild oats brome Trockentrespe Black grass einjähr. cattle grass gr. Foxtail quackgrass Italian ryegrass Bromusrigidus wild knotweed Kochia knotweed wrong camomile Jimhill mustard Wild mustard D. pinnata goosefoot Soot. thistle</td><td>0 0 0 IG 1C.2G 2G 2G 0 0 0 0 9C 9G 9C 9G IOC IOC IOC 8C 3C.5G</td><td>0 IG 2G 3G 1G.3G 3G 3G 0 0 2G 0 9C IOC IOC 9G IOC IOC IOC 9C 7C.7G</td><td>0 IG 3G 5G 2C, 4G 4G 5G IG 2G 3G 0 IOC IOC IOC IOC IOC IOC IOC IOC 8C.8G</td>
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Nr.371668
Table XIX (continued)
<td colspan="4">/<sup>CH</sup>3 / ü \ fi <sup>N</sup>- \ y-SO<sub>2</sub>-NH-C-NH- / Q \ - \<sup>C00_</sup>\ ^ OGH,</td>
<td>kg / ha</td><td>1/64</td><td>1/32</td><td>1.16</td>
<td>Before sprouting wheat barley Wild oats brome Dry trespe Black grass einjähr. cattle grass gr. Foxtail quackgrass Italian ryegrass Bromusrigidus wild knotweed Kochia knotweed wrong camomile Jimhill mustard Wild mustard D.pinnata goosefoot Soot. thistle</td><td>0 0 0 0 0 0 0 0 0 0 0 IOC IOC IOC IOC IOC IOC IOC IOC IOC</td><td>0 0 0 0 0 0 0 IC 0 0 0 IOC IOC IOC IOC IOC IOC IOC IOC IOC</td><td>IC 0 2C 2G 1C.2G 2G 3G 3C IG 2G 0 IOC IOC IOC IOC IOC IOC IOC IOC IOC</td>
Test I
Plastic pots of 127 cm diameter were filled with a mixture of Fallington mud and sand (50:50) and planted with seeds of the following plants (one plant per pot): 5 Morrenia odorata, plantain, Plantago spp., Burdock, arctium minus, field winch, convolvulus arvensis, Dandelion, Taraxacum officinale, Solanum, Solanum carolinense, Bermuda grass, Cynodon dactylon, Field mackerel, Agropyron repens, Dallis grass, Paspalum dilatatum and Johnson grass, Sorghum halepense. The pots were brought into the greenhouse and the plants several
Weeks allowed to grow.
The test compound was diluted with a non-phytotoxic solvent and sprayed on the foliage of the plants. Untreated and solvent sprayed plants were used for comparison. One week and eight weeks after treatment, a visual assessment of the effect of the compound on the growth of the plants was made. The results are given in Table XX. The data show the high activity of the test compound in the control of grown broadleaf and grassy perennial weed species.
Table XX
Perennial broadleaf and grass plants
GH> -N <O >> _M
<img file="AT371668B_D0070.tif" />
CH '
<td rowspan="3">plant species</td><td colspan="4">reviews</td>
<td colspan="2">1 week</td><td colspan="2">8 weeks</td>
<td>1/8 kg / ha</td><td>1/4 kg / ha</td><td>1/8 kg / ha</td><td>1/4 kg / ha</td>
<td>Morrenia odorata</td><td>0</td><td>0</td><td>IOC</td><td>IOC</td>
<td>plantain</td><td>0</td><td>0</td><td>IOC</td><td>IOC</td>
<td>barnacles</td><td>0</td><td>0</td><td>4C</td><td>IOC</td>
<td>bindweed</td><td>0</td><td>2C</td><td>7C</td><td>8C</td>
<td>Dandelion</td><td>0</td><td>0</td><td>IOC</td><td>IOC</td>
<td>nightshade</td><td>0</td><td>IC</td><td>5C</td><td>IOC</td>
<td>Bermuda grass</td><td>5C</td><td>6C</td><td>5C, 7G</td><td>6C.8G</td>
<td>quackgrass</td><td>6C</td><td>7C</td><td>IOC</td><td>IOC</td>
<td>Dalli grass</td><td>6C</td><td>6C</td><td>8C.8G</td><td>IOC</td>
<td>Johnson grass</td><td>8C</td><td>9C</td><td>IOC</td><td>IOC</td>
Test J
The high herbicidal activity of one of the compounds of the formula (I) was confirmed in a field test. The material was applied to a slurry clay prior to sprouting. Three days after the treatment, the area was watered with 2.5 cm of water. Four weeks later the
Percentage of control estimated for each species as shown in Table XXI.
- 155 No.371668
Table XXI
Treatment of crops and weeds before sprouting -% control
<img file="AT371668B_D0071.tif" />
<td rowspan="2"></td><td colspan="5">kg / ha</td>
<td>untreated</td><td>0.031</td><td>0.063</td><td>0,125</td><td>0.25</td>
<td>crabgrass</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>foxtail</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>Cyprus grass</td><td>0</td><td>98</td><td>100</td><td>100</td><td>100</td>
<td>goosefoot</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>ambrosia</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>velvetleaf</td><td>0</td><td>98</td><td>98</td><td>100</td><td>100</td>
<td>reporting</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>purslane</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>knotweed</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>barnyardgrass</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>Rai gras</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>Wild oats</td><td>0</td><td>98</td><td>100</td><td>100</td><td>100</td>
<td>spinach</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>flax</td><td>0</td><td>90</td><td>100</td><td>100</td><td>100</td>
<td>Endive.</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>cabbage</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>Beets</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>carrots</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>lima beans</td><td>0</td><td>50</td><td>60</td><td>70</td><td>90</td>
<td>Green beans</td><td>0</td><td>80</td><td>90</td><td>95</td><td>100</td>
<td>tomatoes</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>Peanuts _______</td><td>0</td><td>70</td><td>80</td><td>90</td><td>90</td>
<td>potatoes</td><td>0</td><td>90</td><td>90</td><td>100</td><td>100</td>
<td>cucumbers</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>pumpkin</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>sugar beets</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>soybeans</td><td>0</td><td>90</td><td>95</td><td>98</td><td>98</td>
<td>alfalfa</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>clover</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>lespedeza</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>cotton</td><td>0</td><td>80</td><td>90</td><td>90</td><td>95</td>
<td>oats</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>Eatable marshmallow</td><td>0</td><td>90</td><td>90</td><td>100</td><td>100</td>
<td>rice</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>wheat</td><td>0</td><td>90</td><td>100</td><td>100</td><td>100</td>
<td>sorghum</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>Corn</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
<td>sunflowers</td><td>0</td><td>70</td><td>90</td><td>95</td><td>100</td>
<td>safflower</td><td>0</td><td>100</td><td>100</td><td>100</td><td>100</td>
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Test K
The response of a number of harmful weed species to the application of the same compound as in Test J after sprouting was examined in another field test. At the time of treatment, 1 month after mowing, the mixed vegetation was about 15 cm high. 5 The chemical was applied in water containing 0.2% of a wetting agent in a total volume of 500 l / ha. Each treatment was repeated three times. 4 Approximately 5 cm of rainfall was noted days after treatment and a further 37 cm of rain fell to 16 assessments post-treatment until the assessments were made. The numbers are given in Table XXII.
Table XXII
Broad Spectrum Weed Control Test Average percentage of weed control
<img file="AT371668B_D0072.tif" />
Weeds per 9.29 dm<sup>s</sup> untreated area of yellow tridentate grass 0,7
Broom 0,7
Goldenrod 1.0
Blackberries 0,5
Poisonous wax 1.0
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4 legal events, as the office reported them to INPADOC
Over the term
Point at a mark for the eventEvents
| Event | Code | |
|---|---|---|
| Grant of a certificate of protectionSZ 36/1997, 19970731, EXPIRES:20051005EZF | EZF | |
| Expired due to lapse of timeExpiredELA | ELA | |
| Application filed for a certificate of protectionSZ 36/1997, 19970731SZA | SZA | |
| Ceased due to non-payment of the annual feeCeasedELJ | ELJ |
Numbers
- Application
- 395979
Titles2
- German
- MITTEL ZUR BEKAEMPFUNG VON UNERWUENSCHTER VEGETATION
- English
- MEANS OF COMBATING UNWIRED VEGETATION
Classification
- CPC, 19
- C07C311/65
- A01N47/28
- A01N47/36
- C07C317/00
- C07C323/00
- C07D239/42
- C07D239/46
- C07D239/47
- C07D239/48
- C07D239/52
- C07D251/14
- C07D251/16
- C07D251/18
- C07D251/46
- C07D251/52
- C07D253/06
- C07D253/07
- C07D253/075
- C07D521/00
- IPC, 26
- A01N
- A01N41 00
- A01N47 28
- A01N47 36
- C07C311 65
- C07D
- C07D239 42
- C07D239 46
- C07D239 47
- C07D239 48
- C07D239 52
- C07D239 69
- C07D251 14
- C07D251 16
- C07D251 18
- C07D251 22
- C07D251 42
- C07D251 46
- C07D251 52
- C07D253 06
- C07D253 07
- C07D253 075
- C07D405 12
- C07D409 12
- C07D413 04
- C07D521 00