Herbicide

261832

The present invention relates to novel herbicidal compositions comprising, as active substance sulfonamides, especially N- (heterocyclo aminocarbonylarylsulfonamides in which the aryl radicals are substituted by a carboxylic acid, ester, thioester or amide group.) The active compounds and their agriculturally suitable salts can be used to for example, herbicides and plant growth regulators In Dutch Patent No. 121,788, the preparation of compounds of the general formula is fluoromethyl or alkyl and their use as antidiabetic agents.

Logemann and co-workers [Chem.Abstr. 53, 18, 052 g (1959)] describe a series of sulfonamides, including uracil derivatives, of formula

O

II

SO2NHCNHR in which

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<img img-format="tif" img-content="drawing" file="CS261852B2D00022.tif" id="idf0002" />

R represents a butyl or phenyl group or a radical of the formula

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in which

R @ 1 and R @ 2 independently of one another are C1 -C4 alkyl, and R3 and R4 are independently hydrogen, chlorine or C1 -C4 alkyl, and the use of said generic or selective games -bicides. U.S. Pat. No. 3,637,366 discloses compounds of the formula and Rx is a hydrogen or methyl group. Compounds in which R is a butyl or phenyl group have a potent hypoglycaemic effect in rats (25 mg / 100 g orally), and other compounds have been less effective or inactive.

Wojciechowski, J. Acta Polon. Pharm. 19, p. 121-125 (1962) [Chem., Abstracts 59, 633e] describes the synthesis of N - [(2,6-dimethoxypyrimidin-4yl] aminocarbonyl] -4- - &lt;5&gt; -SO2-nhr2 in which

R 1 is hydrogen or a lower saturated aliphatic acyl group and R 2 is hydrogen, 2-pyrimidinyl, pyridyl, a-midine, acetyl or carbamoyl. Said compounds can be used to control the growth of bloody rust, cress, ragweed, clover and leek (Poa annua.

In French Patent No. 1,468,747, para-substituted phenylsulfonamides of the formula CH are described,

'/ V

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O

II

S, NHCH3, OCH3, OCH2, and similarity to known compounds of the invention suggests that the above-mentioned substances have hypoglycemic activity.

Substituted pyrimidinyl-arylsulfonylureas, substituted at the para-position of the phenyl ring, of general formula

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CH₃, wherein R is hydrogen or methyl, are described in Pharm. Sci. 12, 586 (1957) [Chem., Abstracts 53, 18, 052g (1959)] wherein R is hydrogen, halogen, tri-261852

It is known that the presence of undesirable vegetation in crops produces considerable damage to their yields, in particular on the yields of those agricultural products which satisfy the basic needs of food and textile fibers for the population such as cotton, rice, maize , wheat, and the like. The current population explosion and its accompanying global shortage of food and textile fibers requires improvements in the efficiency of these cultures. One of the ways to increase their yields is to prevent and reduce the loss of part of the yield of these crops by eradicating or suppressing growth plants. At present, there are many different substances useful for controlling or suppressing the growth of unwanted vegetation, such substances being generally referred to as herbicides. Still, there is still a need for even more effective herbicides.

The present invention provides herbicidal compositions comprising the sulfonamide of the following general formula (I) and their agriculturally acceptable salts, such as sodium, potassium or alkyl chloroformate or salts with trichloroacetic acid. These active compounds are of formula (I) with 2 to 6 carbon atoms substituted with one to four substituents selected from 0 to 3 fluoro, chloro or bromo, from 0 to 2 methoxy and from 9 to 1 cyano; groups of the formulas -CHOCN, -CH2COOCH2-, -CO-COOCd-1; C 3 -C 6 alkenyl substituted with 1 to 3 atoms from the group consisting of F, Cl and Br; C5-C8 cycloalkyl; a cycloalkenyl group having from 5 to 8 carbon atoms; a cycloalkyl group of 5 to 6 carbon atoms substituted by one to four methyl groups, methoxy groups, C 2 -C 4 alkyl, fluoro, chloro or bromo; cycloalkylalkyl of 4 to 10 carbon atoms; cycloalkylalkyl of 4 to 8 carbon atoms substituted with 1 to 2 methyl groups; bicycloalkyl of 7 to 10 carbon atoms; bicycloalkenyl having 7 to 10 carbon atoms; a tricycloalkyl group having 10 carbon atoms; tricycloalkenyl having 10 carbon atoms; a group of the formula R? tricycloalkenyl having 10 carbon atoms; a group of the formula R? tricycloalkenyl having 10 carbon atoms; a group of the formula R?

<img img-format="tif" img-content="drawing" file="CS261852B2D00031.tif" id="idf0006" />

R,

W

II s-2-c-R 1 /

-CQR IIo

NR

Wherein R 1 is hydrogen, alkyl having 1 to 3 carbon atoms or a hydrogen atom; R 1 and R 2 are each independently hydrogen, alkyl of 1 to 3 carbon atoms , bromine, inethoxy, ethoxy, or R 10 and R 10 together form a 6- to 6-membered ring of the formula wherein Q represents an oxygen, sulfur or a group of oxygen;

<img img-format="tif" img-content="drawing" file="CS261852B2D00032.tif" id="idf0007" />

R a and when Q is oxygen or sulfur, then R is C 1 -C 12 alkyl; alkenyl having from 3 to 10 oxygen atoms; an alkyl group being 0, 1, 2 or 3, with the proviso that the total number of carbon atoms is equal to or less than 12; groups of formulas 261852 »

<img img-format="tif" img-content="drawing" file="CS261852B2D00041.tif" id="idf0008" />

in which A represents an oxygen or sulfur atom; A, an oxygen atom, a sulfur atom or a SO2 group; and when Q represents an oxygen atom, then R represents a hydrogen atom; M; groups of general formula -CH3CH3OR7, -CH2CH2CH2OR7 or -CH-CH2OR7, wherein R7 is ethyl, isopropyl, phenyl, 2-chloroethyl or 2,2,2-trichloroethyl; groups of the formulas (-CH2CH2O-n-Re or CH3 in which R8 represents methyl, ethyl, isopropyl, phenyl, 2-chloroethyl or 2,2,2-trichloroethyl and the number 2 or 3, provided that the total number of carbon atoms in the substituent R is equal to or less than 13; the groups of the general formula -CH2CH2-S-R12 or -CH2CH2CH2-S-R12 in which R12 is methyl, ethyl, isopropyl or phenyl; represents a group of the formula -N

AND

Re then R is hydrogen; an alkyl group having 1 to 12 carbon atoms; a group of the formula (-CH3CH2O-) n-R12 or -CH2CH2CH2OR12 in which

R 2 is as defined above and is 1 to 3; C 3 -C 10 alkenyl; a cycloalkyl group having from 3 to 8 carbon atoms; cycloalkenyl of 5 to 6 carbon atoms; cycloalkyl having 5 to 8 carbon atoms substituted with 1 to 3 substituents selected from 0-2 methoxy, from 0-3 methyl or ethyl; trifluoromethylcyclohexyl; cycloalkylalkyl of 4 to 10 carbon atoms; cycloalkylalkyl of 4 to 8 carbon atoms substituted with 1 to 2 methyl groups; groups of formulas 261852 -CH2CN; -CH2CH2CN; CH (CH 2) 2 - (CH 2) n R 10, nitrile, nitro, groups of the formulas -SO 2 CH 3, -SCH3 or -N (CH3) 2;

<img img-format="tif" img-content="drawing" file="CS261852B2D00051.tif" id="idf0009" />

R &amp; quot; represents a hydrogen atom, a C 1-4 alkyl group, a methoxy group or a fluorine, bromine or chlorine atom; R &amp; quot; represents a hydrogen atom, a methyl group or a chlorine, fluorine or bromine atom;

R6 is hydrogen, C1 -C6 alkyl, allyl, -CH2 CN or -CH2 CH2 CN; or R6 and R5 together may form a residue of the formula in which n, R6, R6 and R6 are as defined above; - [CH 2) 5 -, - (CH 2) 6 -, -CH 2 CH 2 OCH 2 CH 2 -, or -

<img img-format="tif" img-content="drawing" file="CS261852B2D00052.tif" id="idf0010" />

in which R 1 is hydrogen, C 1 -C 4 alkyl, methoxy, fluoro, bromo or chloro, trifluoromethyl, -CH 2 CH 2 -N-CH 2 NH 2, with the proviso that when R is methoxy, then R 6 is methyl ; when R6 is -CH2CH2CN or -CH3CN then R is -CH2CH2CN or -CH2CN; and R6 and R6 have a total number of carbon atoms equal to or less than 13;

R1 stands for groups of formulas

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and

N ~ NN ~

(CH2) 2 -CH3, -CH3, -cf3, -N (CH3) 2, -N (CH3) 2, -NH2 or CN; R3 represents a hydrogen, chlorine, bromine or fluorine atom or a methyl group; R4 represents a hydrogen atom or a methyl group; R5 represents a hydrogen atom, a methyl group or a methoxy group; M is an alkali metal atom; W represents an oxygen or sulfur atom; X is hydrogen, chlorine, methyl, methoxy, ethoxy or -OCH 2 CH 2 OCH 3; Y represents hydrogen; a chlorine atom; C 1 -C 4 alkyl, optionally substituted with the groups of the formulas -OCH 3, -OC 2 H 5, -CN, -COOCH 2, -COOC 2 H 5, or 1 to 3 fluorine, chlorine or bromine; alkenyl of 3 to 4 carbon atoms; a group of the formula -CH2C = CR13, in which R13 represents a hydrogen atom, a methyl group or a group -CH3Cl; a group of the formula -A- (CH 2) n -Ax- (C 1 -C 3) alkyl, wherein n 'A and A 1 are as defined above; groups of formulas 12

O

II-AUC2C-L, o

II

-A-CH-C-Lh3 or

O-A-CH 2 CH 2 C-L, wherein L is a radical of formula -NH 2, -NH 3, OCH 2, -NH- (C 1 -C 6 alkyl, N - [(C 1 -C 6) alkyl or C 1 -C 6 alkoxy; groups of formulas-SCN; -N3; ​​-NR16R17 wherein R16 is hydrogen or methyl and R17 is hydrogen, methoxy, C1-4 alkyl, optionally substituted -CN, -COOCH3 or -COOC 2 H 5, C 3 -C 4 alkenyl or C 2 -C 3 alkyl substituted by methoxy or ethoxy, or R 9 and R 17 form together a group of the formula -CH 2 CH 3 CH 2 CH 2 - or -CH 2 CH 2 OOCH 2 CH 2 - a group of the formula -O-R144 26185213 in which

R m is C 1 -C 4 alkyl, C 2 -C 4 alkyl substituted with 1 to 3 fluorine, chlorine or bromine, C 1 -C 4 alkyl substituted by cyano, C 3 -C 4 alkenyl carbon atoms, -CH 2 C = CR 1;

R &amp; lt; 3 &amp; gt; is as defined above, or a group of the formula -C (R6) 2; a group of formula s-R15 in which

R 1 5 is C 1 -C 4 alkyl, C 1 -C 2 alkyl substituted by nitrile, allyl or propargyl, with the proviso that when the number of carbon atoms of the Y substituent is equal to or greater than 4 , the number of carbon atoms in the substituent R is equal to or less than 4, and when X is a chlorine atom, Y is also chloro, and when X and Y are atoms of the carbon, the number of carbon atoms in the substituent R is equal or * less than 4; Z denotes a group -CH- or a nitrogen atom; Y represents a hydrogen atom, a methoxy group or a methyl group; and

X1 is hydrogen, chloro, methoxy, ethoxy or methyl; with the proviso that both substituents represent X (and Y (současněatoimy not represent hydrogen and that when R | represents a radical of the formula 14 2. Compounds of formula I in estradiol which R4 and R5 represent hydrogen atoms, W značíatom oxygen and carbon, which is the substituent R bonded to Q is also bound at least a single hydrogen atom. 3. the preferred compounds according to point 2TY compounds of formula I wherein R2 is hydrogen, chlorine, bromine nebofluoru, C group having 1-3 atomyuhlíku, nitro, methoxy neboskupiny formulas -SCH? "--SO2CH; 1 -CF j, - N (CH,) 2, -NH 2 and -CN, and R :( represents hydrogen, which is in the para-position to a sulfonyl group 4. Of the preferred compounds according to item 3 of the compound of formula I, in which Q represents an oxygen or sulfur atom and R represents a C 1 -C 6 alkyl group, an alkenyl group having 3 to 6 carbon atoms; alkyl of 2-4 carbon atoms substituted with one to four substituents selected from 0 to 3 fluoro or chloro, from 0 to 2 methoxy and from 0 to 1 cyano; a group of the formula CH2CN; an alkenyl group of 3 to 4 carbon atoms substituted with 1 to 3 amino atoms; cycloalkyl having 5 to 6 carbon atoms; cycloalkenyl of 5 to 6 carbon atoms; a C 5 -C 6 cycloalkyl group substituted with one to four methyl groups, methoxy groups, ethyl groups or chlorine atoms; cycloalkylalkyl of 4 to 7 carbon atoms; a group of the general formula -CH- (CH 2) 2 R 2 alkyl of 2-4 carbon atoms substituted with one to four substituents selected from 0 to 3 fluoro or chloro, from 0 to 2 methoxy and from 0 to 1 cyano; a group of the formula CH2CN; an alkenyl group of 3 to 4 carbon atoms substituted with 1 to 3 amino atoms; cycloalkyl having 5 to 6 carbon atoms; cycloalkenyl of 5 to 6 carbon atoms; a C 5 -C 6 cycloalkyl group substituted with one to four methyl groups, methoxy groups, ethyl groups or chlorine atoms; cycloalkylalkyl of 4 to 7 carbon atoms; a group of the general formula -CH- (CH 2) 2 R 2 alkyl of 2-4 carbon atoms substituted with one to four substituents selected from 0 to 3 fluoro or chloro, from 0 to 2 methoxy and from 0 to 1 cyano; a group of the formula CH2CN; an alkenyl group of 3 to 4 carbon atoms substituted with 1 to 3 amino atoms; cycloalkyl having 5 to 6 carbon atoms; cycloalkenyl of 5 to 6 carbon atoms; a C 5 -C 6 cycloalkyl group substituted with one to four methyl groups, methoxy groups, ethyl groups or chlorine atoms; cycloalkylalkyl of 4 to 7 carbon atoms; a group of the general formula -CH- (CH 2) 2 R 2 an alkenyl group of 3 to 4 carbon atoms substituted with 1 to 3 amino atoms; cycloalkyl having 5 to 6 carbon atoms; cycloalkenyl of 5 to 6 carbon atoms; a C 5 -C 6 cycloalkyl group substituted with one to four methyl groups, methoxy groups, ethyl groups or chlorine atoms; cycloalkylalkyl of 4 to 7 carbon atoms; a group of the general formula -CH- (CH 2) 2 R 2 an alkenyl group of 3 to 4 carbon atoms substituted with 1 to 3 amino atoms; cycloalkyl having 5 to 6 carbon atoms; cycloalkenyl of 5 to 6 carbon atoms; a C 5 -C 6 cycloalkyl group substituted with one to four methyl groups, methoxy groups, ethyl groups or chlorine atoms; cycloalkylalkyl of 4 to 7 carbon atoms; a group of the general formula -CH- (CH 2) 2 R 2

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<img img-format="tif" img-content="drawing" file="CS261852B2D00072.tif" id="idf0013" />

then the two substituents R 4 and R 5 are hydrogen atoms and the number of carbon atoms in the substituent R is equal to or less than 5. More preferred are the following compounds of formula I: wherein R 9 is hydrogen or methyl, n is 0 or 1 and R (O and Rtt independently of one another are hydrogen, methyl, chloro or methoxy and groups of formulas 261852, 13b

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cycloalkyl having 6 carbon atoms substituted by 1 to 2 methoxy or 1 to 3 methyl or ethyl groups; trifluoromethylcyclohexyl; cycloalkylalkyl of 4 to 7 carbon atoms; -CH2CN, -CH2CH2CH2CH2CN, CH3-C-CN, CH3-CH3,

<img img-format="tif" img-content="drawing" file="CS261852B2D00082.tif" id="idf0015" />

in which R 1 is hydrogen, R 11 is hydrogen, C 1 -C 4 alkyl, methoxy or fluoro, bromo or chloro, and R 11 is hydrogen, methyl or chloro, fluoro or bromo; group of the general formula

<img img-format="tif" img-content="drawing" file="CS261852B2D00083.tif" id="idf0016" />

/ wherein R9 is hydrogen or methyl, and R10 and R11 are independently hydrogen, methyl, chloro or methoxy; and R6 is hydrogen, alkyl of 1 261 852 17-3 C atoms or groups obecnýchvzorců -CH2CN, -CH2CH2CN, -CHjCII - CH j, or R and R together form ITUH skupinyvzorců -CH CÍI20il: 0H2-, -CH2CH2CH2CH2CH ? - or - CH 2 CH 2 OCH 2 CH 2 -. 7. Preferred compounds according to paragraph 3ty compound of formula I in kterémX is methyl, or e-methoxylovcu thoxylovotu and Y represents atomvodíku; alkyl of 1 to 4 carbon atoms; alkyl having 1-2 atomyuhlíku substituted by a group of formula - OCH) ~ oc2I-IR "-CN, -COOCH i, -COOC2H5, or 1 to 3 fluoro or chloro atoms; a C 3 -C 4 alkenyl group; a group of formula -0014,000 (C 1 -C 10) alkyl;

R @ 7 is C1 -C4 alkyl, C2 -C3 alkyl substituted by 1 to 3 fluoro or chloro, C1 -C3 alkyl substituted by cyano, C3 -C4 alkenyl; -SCH2; group-SC2H5; a group of the formula ## STR6 ## in which R1 represents a hydrogen atom or a methyl group and R17 represents a C1 -C4 alkyl group, a C1 -C4 alkyl group substituted by a cyano group, an alkyl group having from 2 to 3 carbon atoms and X and Y are as defined above 8. Among the preferred compounds of item 7 of the formula I wherein Q is as defined in 4.9. Of the preferred compounds according to item 7 of the compound of formula I, wherein the -QR substituent is as defined in claim 5. 10. Preferred compounds according to item 7 of a compound of formula I in which -QR is as defined in item 6. 11. Among the preferred compounds according to points 8, 9 or 10 those compounds of general formula of formula I wherein R @ 3 represents a hydrogen atom, an atom of chlorine or a methyl group. 12. Of the preferred compounds according to item 11 of a compound of the formula I in which Q represents an oxygen or sulfur atom and Rrepresents an alkyl group having 1 to 4 carbon atoms; alkenyl of 3 to 4 carbon atoms; an alkyl group of 2 to 3 carbon atoms substituted by methoxy, a chlorine or a nitrile group; a group of formula -CH2CN; an alkenyl group having 3 carbon atoms substituted with 1 to 3 chlorine atoms; (C5 -C6) cycloalkyl; cyclohexenyl; cyclohexyl groups substituted with 1 to 3 methyl groups; group of the formula

~ CH in which

R9 is hydrogen or methyl, n is zero or one and R10 and R10 independently of one another are methyl, methoxy or chloro. 13. Among the preferred compounds of the formula I, compounds of the formula I in which Q represents an oxygen atom and R represents a hydrogen atom, M represents a group -CH2CH2OR7, wherein R7 represents an ethyl, isopropyl, phenyl or 2-chloroethyl group ; of the formula -CHCH2 OC2 H5. 14. Of the preferred compounds according to item 11 of a compound of the formula I in which Q represents a group of formula -NR6- wherein R6 represents a hydrogen atom, a methyl or ethyl group, and R represents an alkyl group of 1 to 4 carbon atoms a group of the formula -CH2CH2OCH3 or -CH2CH2OC2H5; a C 3 -C 4 alkenyl group; cycloalkyl having 5 to 6 carbon atoms; cyclohexyl substituted with 1 to 3 methyl groups; group of the formula

<img img-format="tif" img-content="drawing" file="CS261852B2D00101.tif" id="idf0017" />

in which R &amp; quot; represents a hydrogen atom, a methyl group or a chlorine atom, R 1 represents a hydrogen atom and R 11 represents a hydrogen atom, a methyl group or a chlorine atom; or a benzyl group; or R and R6 may form a group of the formula -CH2CH2CH2CH2- or -CH2CH2OCH2CH2-. 15. Among the preferred compounds of the formula I, compounds of formula (I) in which R @ 1 denotes a radical of general formula

<img img-format="tif" img-content="drawing" file="CS261852B2D00102.tif" id="idf0018" />

in which X is methyl, methoxy or ethoxy and Y is hydrogen, alkyl of 1 to 3 carbon atoms, -CH2 OCH3, -CH2OC2H5, -OCH2COO- (C1-C12alkyl), -OCH-COO- (C1-C2) , CH 3 -O (C 1 -C 3) alkyl or -O- (C 3 -C 4) alkenyl, or a group of the formula -NR k R 17 wherein R 16 is hydrogen or methyl and R 17 is C 1 -C 3 alkyl , and Z represents a group -CH- or a nitrogen atom. 16. Among the preferred compounds of the formula I, the compound of the formula I in which-QR has the meaning given in 12. 12. Preferred compounds of the formula I in which the -QR substituent is as defined in Section 13. 18. Of the preferred compounds according to item 15 those compounds of the formula I in which the -QR substituent is as defined in item 14. 19. Of the preferred compounds of points 16, 17 or 18 those compounds of formula I wherein R2 and R3 are hydrogen. 20. Of the preferred compounds according to item 19 of a compound of the formula I in which Q represents an oxygen atom and R represents an alkyl group of 1 to 4 carbon atoms; a C 3 -C 4 alkenyl group, a C 2 -C 3 alkyl group substituted by a chlorine atom; (CH 3 or C 2 H 5), -CH 2 CH 2 O- (CH 3 or C 2 H 5), or

ICH3-CH2CH2CH2O- (CH3 or C2H5). 21. Of the preferred compounds according to item 19 of the compound of formula I wherein S is sulfur and R is C1 -C4 alkyl or C3 -C4 alkenyl. 22. Among the preferred compounds of formula (19), compounds of the formula (I) in which Q represents a group of the formula -NR (i- and R represents a C 1 -C 4 alkyl group, a C 3 -C 4 alkenyl group and a group of the formulas -CH 2 CH 2 O- CH 2 or CH 2) or -CH 2 CH 2 CH 2 O- (CH 3 or C 2 H 6), and R 1 represents a hydrogen atom or a methyl group, or R 2 and R 2 together form a group of the formula (CH 2) 4 or -CH 2 CH 2 OCH 2 CH 2 - 23. Of the preferred compounds according to item 19 of a compound of formula I wherein X is methyl,

by reacting an appropriately substituted o-carbonylbenzenesulfonyl isocyanate or i -othiocyanate with the corresponding aminopyridine or aminotriazine. The compounds of the formula (I) thus obtained can be converted to other compounds of formula (I) as shown in the other reaction equations. O-carbonylbenzenesulfonylisocyanates and sulfonylisothiocyanates are therefore important intermediates for the preparation of the compounds of formula I. The synthesis of these intermediates is illustrated in Reaction Schemes 1 and 2. by reacting an appropriately substituted o-carbonylbenzenesulfonyl isocyanate or i -othiocyanate with the corresponding aminopyridine or aminotriazine. The compounds of the formula (I) thus obtained can be converted to other compounds of formula (I) as shown in the other reaction equations. O-carbonylbenzenesulfonylisocyanates and sulfonylisothiocyanates are therefore important intermediates for the preparation of the compounds of formula I. The synthesis of these intermediates is illustrated in Reaction Schemes 1 and 2.

Equation 1

COOR X x SOgNHjCOClg

DA &amp; amp; CO

N CO xylene. reflU '*

COOR

SO 2 NCO 3 7?

<img img-format="tif" img-content="drawing" file="CS261852B2D00121.tif" id="idf0019" />

R3 r2 from

In the above reaction equation, Q denotes an oxygen atom, R is an alkyl group of 1 to 12 carbon atoms; alkenyl of 3 to 10 carbon atoms; C 2 -C 6 alkyl substituted with one to four substituents selected from 0-3 fluoro, chloro or bromo and from 0 to 2 methoxy; C 3 -C 6 alkenyl substituted with 1 to 3 fluoro, chloro or bromo; C5-C8 cycloalkyl; cycloalkenyl of 5 to 8 carbon atoms; cycloalkyl of 5 to 6 carbon atoms substituted with one to four methyl groups, methoxy groups, C2-C4 alkyl groups or fluorine, chlorine or bromine atoms; cycloalkylalkyl of 4 to 10 carbon atoms; a cycloalkylalkyl group of 4 to 8 carbon atoms substituted with 1 to 2 methyl groups; a group of the groups -CH2CH2OR7, -CH2CH2CH2OR7 or -CH-CH2OR7, wherein R7 is ethyl, isopropyl, phenyl, 2-chloroethyl or 2,2,2-trichloroethyl; or groups of formulas (-CH 2 CH 2 O-) n &lt;-R 8, (-CHCH 2 O-) n -R g, in which

R9 is methyl, ethyl, isopropyl, phenyl, 2-chloroethyl or 2,2,2-trichloroethyl and the number 2 or 3; R2 is hydrogen, chlorine, bromine or fluorine, alkyl of 1 to 3 carbon atoms, nitro, methoxy, or a group of the formula: (I) 2 or -CN; and R @ 2 (hydrogen, chlorine or bromine or methyl).

The obtained residue is the crude sulfonyl isocyanate of formula II. In the case where the symbol W represents a sulfur atom in the general formula I, the corresponding sulfonyl isothiocyanate required as the intermediate product is prepared as shown in reaction equations 2 and 2 '.

Equation 2

O

<img img-format="tif" img-content="drawing" file="CS261852B2D00131.tif" id="idf0020" />

cociz xylene

DMF W -&gt;

<img img-format="tif" img-content="drawing" file="CS261852B2D00132.tif" id="idf0021" />

+ KCl

According to reaction equation 2, the o-carbonyl-substituted sulfonamide is dissolved in dimethylformamide (DMF), an equivalent amount of carbon disulfide is added and potassium hydroxide equivalents are added in portions at room temperature. The mixture is stirred for 1 to 8 hours and then diluted with ethyl acetate, ethyl ether or similar aperture solvent to precipitate the dibasic salt of the corresponding dithiocarbamic acid. The salt is isolated, dried and suspended in an inert solvent such as xylene, benzene, tetrachloromethane or methylene chloride. Suspension is carried out with stirring, at a temperature below room temperature, phosgene and then stirred for 1 to 3 hours. Instead of phosgene, it is also suited to use chloromethanesulfonic acid esters (e.g., methyl chloroformate), phosphorus pentachloride, sulfuryl chloride or thionyl chloride.

The resulting sulfonyl isothiocyanate is usually soluble in the solvent used and is conveniently isolated by filtration of the inorganic part (potassium chloride) and distilling off the solvent to give the isothiocyanates which are mostly unstable and readily dimerised (see reaction equation 2 '), but the dimers can be used in the process according to the invention as well as the original monomers.

Equation 2 '

<img img-format="tif" img-content="drawing" file="CS261852B2D00141.tif" id="idf0022" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00142.tif" id="idf0023" />

II

O

The choice of the synthetic method for the preparation of the compounds of the formula I depends to a large extent on the nature of the substituents R and R1. As can be seen from reaction formula 3, a compound of formula I in which Q, R, R 2 and R 3 are as defined in Equation 1 can be conveniently prepared by reacting an appropriately substituted carbonylbenzenesulfonylisocyanate or isoithiocyanate of formula libs with an appropriately substituted aminopyrimidine or aminotriazine of formula III.

Equation 3

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C11b) (III) 0

<img img-format="tif" img-content="drawing" file="CS261852B2D00144.tif" id="idf0025" />

(AND)

The reaction according to equation 3 is preferably carried out in an inert aprotic organic solvent such as methylene chloride, tetrahydrofuran or acetonitrile, at atmospheric pressure and at room temperature. The process of adding the reactants is not critical, but it is usually convenient to add a sulfonyl isocyanate or isothiocyanate with stirring to a suspension of the amine of general formula III.

Since the isocyanates and isothiocyanates used are liquids or low melting solids, or they are easily dissolved in conventional solvents, for example those mentioned above, their addition to the reaction mixture can be easily controlled.

The reaction is generally exothermic. In some cases, the desired product is soluble in the hot reaction mixture and, after cooling, crystallizes in pure form. Other reaction products are soluble in the reaction medium and can be isolated, for example, by distilling off the solvent, stripping the solid with a suitable solvent such as 1-chlorobutane or ethyl ether and filtering off the product.

Compounds of formula Ia in which R is other than hydrogen or M, W is sulfur and R5 is hydrogen can alternatively be prepared by reacting an appropriately substituted o-carbonylbenzenesulfonamide with the appropriate triazine or pyrimidine isothiocyanate of formula as shown in the following reaction box 3A. 261852 29 30

Equation 3A

<img img-format="tif" img-content="drawing" file="CS261852B2D00151.tif" id="idf0026" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00152.tif" id="idf0027" />

The reaction according to equation 3A is preferably carried out by adding a base equivalent such as potassium carbonate to the solution or to the suspension of the sulfonamide and the corresponding isethiocyanate in a polar solvent such as, for example, v acetone, acetonitrile, ethyl acetate or methyl ethyl ketone, and the mixture is stirred in a temperature ranging from room temperature to the boiling point of the reaction mixture for 1 to 25 hours. In some cases, the desired product from the reaction mixture is eliminated and isolated by mere filtration. The dry product is then stirred with dilute mineral acid, filtered and washed with water. If the product of the reaction mixture is not eliminated, it can be isolated that the solvent is distilled off, the solid is triturated with the dilute mineral acid and the insoluble product is filtered off.

The heterocyclic isothiocyanates used in the process of Equation 3A can be prepared, for example, by the method described in Japanese Patent Application Kokai 51-143 686 of 5 June 1976 or by the method described by W. Abraham and G. Barni-kow in Tetrahedron 29, 691-687 (1973).

Compounds of the formula I in which Q represents an oxygen atom, a sulfur atom or an -N-,

Rc, R is as defined in Equation 1, R 4 is methyl and W is oxygen can be prepared by methylation of a salt of general formula IV in which M represents an alkali metal catholyte, for example, a cation of a salt (derived from compounds of general formula I, represents a hydrogen atom) as shown in the following reaction equation 4.

Equation 4

<img img-format="tif" img-content="drawing" file="CS261852B2D00153.tif" id="idf0028" />

QR

In the above equation, X denotes an anion which is anionic in the reaction and is the integer of the corresponding X.

The reaction according to equation 4 is preferably carried out in an aprotic organic solvent, such as tetrahydrofuran, dimethylformamide or dimethylacetamide, at atmospheric pressure and at room temperature. Standard methylating agents of formula V, such as dimethyl sulphate or methyl iodide, can be used for methylation. The desired compound of formula Ib can be isolated, for example (Rk XR,

<img img-format="tif" img-content="drawing" file="CS261852B2D00154.tif" id="idf0029" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00155.tif" id="idf0030" />

(B) so that the reaction mixture is poured into water and the solid product is filtered off.

Compounds of formula (Ic) in which Q represents an oxygen atom, a sulfur atom or a group of the formula -N-,

R 6 and R 4 are as described in Equation 4, the correspondingly substituted sulfonyl-N-methylcarbamoyl chloride or sulfonyl N-methylthiocarbamoyl chloride of the formula VI can be prepared with the corresponding aminopyrimidine or aminotriazine formula III, as shown in the following reaction equation 5.

<img img-format="tif" img-content="drawing" file="CS261852B2D00161.tif" id="idf0031" />

(VI) 0 &amp; quot;)

<img img-format="tif" img-content="drawing" file="CS261852B2D00162.tif" id="idf0032" />

C) The preparation of ureas and thioureas from amines and carbamoyl chlorides is well known to those skilled in the art; the urea and thiourea of ​​general formula Ic can be prepared in a similar manner. The reaction is preferably carried out by reacting a corresponding amount of the general formula (VI) and amine (III) in an inert organic solvent such as tetrahydrofuran, xylene or methylene chloride in the presence of an acid acceptor such as triethylamine, pyridine or sodium carbonate, at a temperature of 20 to 130 ° C. If the product formed in the solvent used is soluble, it can be isolated by removing the precipitated salts and filtering the filtrate. If the product formed is insoluble, it can be filtered off and washed with salt by washing with water.

The chlorides of formula (VI) can be prepared by treatment with phosgene or thiophosgene on N-alkylsulfonamide salts. The corresponding sulfonamide salt is introduced into a solution of excess phosgene or thiophosgene in an inert organic solvent such as tetrahydrofuran, toluene or xylene, and removal of the excess phosgene or thiophogen, the resulting chloride VI is either isolated or used directly , in situ, to react with an amine of formula (III).

Compounds of formula (Ie) in which R is hydrogen may be prepared by hydrolysis of esters of formula (Id) wherein R is C 1 -C 12 alkyl. As shown in Reaction Scheme 6, the alkali metal hydroxide-catalyzed hydrolysis, in the presence of methanol, yields the salt of the corresponding alkali metal carboxylic acid from which the free carboxylic acid is reacted with a mineral acid such as hydrochloric acid. 261852 33 34

Equation 6

<img img-format="tif" img-content="drawing" file="CS261852B2D00171.tif" id="idf0033" />

The reaction according to equation 6 is preferably carried out in such a way that a solution of the compound to be hydrolyzed in a mixture of 2 to 10 parts of ethanol, 10 to 50 parts of water and 2 to 10 equivalents of a base such as sodium or potassium hydroxide, heated for 3 to 24 hours at 30 to 90 ° C. The reaction produces a soluble carboxylic acid salt with an alkali metal which can also be used in the present invention. The obtained salt can be converted to free acid so that a strong mineral acid, such as hydrochloric acid or sulfuric acid, is added to the reaction medium after completion of the hydrolysis.

Rf RS 1

c-OH

II

The desired carboxylic acid is precipitated from the solution from the solution.

Compounds of formula I wherein W and Q are O and R are hydrogen may be readily converted to compounds of the formula I in which R is higher alkyl or substituted alkyl such that the salt-in I in which R represents a hydrogen atom) is reacted with the corresponding halide of the formula R-Hal as shown in reaction equation 6A.

Equation 6A

<img img-format="tif" img-content="drawing" file="CS261852B2D00172.tif" id="idf0034" />

O

II

C-OH

<img img-format="tif" img-content="drawing" file="CS261852B2D00173.tif" id="idf0035" />

venides. A-halonitriles or .alpha.-haloalkenyl compounds.

The reaction according to equation 6A is preferably carried out in inert polar solvents such as tetrahydrofuran, acetonitrile

The reaction is applicable when the corresponding halide of formula R-Hal contains easily substitutable halogen, such as in the case of substituted or unsubstituted allyl or benzyl halides or acetone, in that a suitably substituted carboxylic acid is treated with a suitable base, such as triethylamine or 1,4-diaza [2,2,2] bicyclooctane, to the salt, the appropriate halide is added and the mixture is heated to reflux with stirring for 1 to 16 hours. The solvent is distilled off, the trituration water is evaporated and the product is filtered off and washed with water to give a water-soluble salt. 1 i.

<img img-format="tif" img-content="drawing" file="CS261852B2D00181.tif" id="idf0036" />

(If)

Compounds of formula (I) in which n is -NR6- may be prepared by reacting esters of general formula (I) in which R is C1 -C4 alkyl, preferably methyl, with the corresponding dialkylammonium N -alkylamides. The process is illustrated in Reaction Formula E wherein R, R1, R2, R8 and R6 are as defined above. toluene The corresponding alkylaminoaluminium compounds prepared according to A. Basha, M. Lipton and SW Weinreba, Tetrahedron Letters 4171 (1977) are mixed with a suspension of the resulting ester in a toluene or a similar inert solvent and a mixture it is allowed to boil for one to six hours under reflux condenser. The desired product is isolated by removal of the solvent (toluene), methylene chloride is added to the residue, the reaction mixture is quenched with aqueous hydrochloric acid and the product is taken up in methylene chloride. After removal of the solvent, the desired product is obtained in a sufficiently pure form, sufficient to meet the needs of the present invention.

Compounds of the formula ## STR2 ## in which Q represents a group of the formula -NR3- and the substituents R1, R2, R3 and R4 are as defined above, which are required as intermediates in the process of reaction equation 3A , can be prepared as shown in the following equation 7A

Equation 7A.

R

<img img-format="tif" img-content="drawing" file="CS261852B2D00191.tif" id="idf0037" />

COOCH, toluene (IIc) and R. 3.

<img img-format="tif" img-content="drawing" file="CS261852B2D00192.tif" id="idf0038" />

R&gt;

SO2 NH2 R, (lid)

The reaction conditions described for the preparation of the compounds according to equation 7 are also suitable for the preparation of the esters of the formula IIIa naamides of the formula: Lid, as shown in equation 7A.

The products obtained by the method of Equation 7A are particularly suitable for the preparation of compounds of formula Ia in which Y has a substituent of the formula -COO- (C 1 -C 6) alkyl as shown in Equation 3A.

Compounds of formula (I) in which Q represents a sulfur atom can be prepared from esters of formula (I) in which the group-QR represents a C1-4 alkoxy group, preferably a methoxy group, in that the said esters are reacted with the corresponding dialkylaluminum alkylthiolate according to equation 8.

Equation 8

<img img-format="tif" img-content="drawing" file="CS261852B2D00193.tif" id="idf0039" />

R ~ S ~~ A-CH3

SR

<img img-format="tif" img-content="drawing" file="CS261852B2D00194.tif" id="idf0040" />

As intermediates, aluminum thiolates may be prepared as described by RP Hatch and SW Weinreb in Journal of Organic Chemistry, Vol. 42, p. 3, 980 (1977). The reaction of the aluminum thiolate with the ester of general formula I is carried out in a neutral solvent such as toluene or xylene while heating the mixture under reflux for 1 to 3 hours. Better yields can be obtained by using aluminum thiolate in the desired stoichiometric amount.

Above in equation 8 described by R. R. Hatche and SW Weinreba, the carboxylic acid esters of sulfonamides of formula (IIb) in which R, R2, R3 and R4 are as hereinbefore defined may also be converted to the corresponding thiolesters, such as the vortical equation 8A is shown.

<img img-format="tif" img-content="drawing" file="CS261852B2D00201.tif" id="idf0041" />

toluene RS-Al-CH3

F sharp

8A

<img img-format="tif" img-content="drawing" file="CS261852B2D00202.tif" id="idf0042" />

The reaction conditions described in the manner of equation 8 are also suitable for converting sulphonamides of the formula lithium to thioesters as shown in Equation 8A.

The product obtained by the method of Equation 8A is particularly suitable for the preparation of compounds of formula Ia in which the group Y carries an ester substituent of the formula -COO- (C 1 -C 6) alkyl by the procedure described in Equation 3A.

An alternative process for the preparation of a compound of formula (I) in which Q is an oxygen atom and R is bonded to a carbon atom is a reaction of the corresponding dialkylaluminum alkoxide with an ester of the formula I wherein R is lower primary alkyl group, preferably methyl. This alternate procedure is shown in Reaction Sheet 9.

Equation (9), COOCH3 O + (CHAAt-O-sec-alkyl SO2NHCNH2)

The reaction is carried out in a neutral solvent having a sufficiently high boiling point, for example in toluene, which allows the reaction to be heated under reflux with a reflux condenser. In order to obtain higher yields, the dialkylaluminum alkoxide is preferably used in a larger than an evan-valent amount relative to the starting ester. The reaction mixture is heated to reflux for 1 to 15 hours, then cooled, quenched with dilute hydrochloric acid and taken up in methylene chloride. After distilling off the solvent, the desired ester is obtained in a purity sufficient for the purposes of the present invention. In order to remove a small amount of impurities, the suction product can be triturated with a suitable solvent, for example with 1-chlorobutane.

Synthesis of the necessary heterocyclic amines can be found in "The Chemistry 2 618 S 2 41 of Heterocyclic Compounds", published by Interscience Publ., New York, and London. 2-Aminopyrimidines are written by DJ Brownern in "The Pyrimides", in the XVI volume of this series. 2-Amino-1,3,5-triazines are described by KR Huffman in the "The Triazines" of the same sequence. Synthesis of triazines is also described by F. C. Schaefer in U.S. Pat. No. 3,154,547, and KR Huffman and FC Schaeferm in J. Org. Chem. 28, 1818-182 (1963).

The process for the preparation of the compounds of formula I is further illustrated by the following embodiments in which the temperature is in degrees Celsius and parts, unless otherwise indicated, are the masses. Example 1

Methyl-2- (isocyanatosulfonyl) benzoate

A mixture of 157 g of methyl-2-sulfamoylbenzoate, 73 g of butyl isocyanate, 0.3 g of 1,4-diazabicyclo [2.2.2] octane and 1.0 l of xylene is heated under reflux for half an hour. The reaction mixture is then subjected to refluxing with carbon dioxide gas, phosgene gas, until the reaction temperature drops to 120 ° C. The phosgene addition is continued for as long as the boiling point of the reaction mixture remains at 120 ° C without further phosgene addition. The temperature of the reaction mixture is then raised to 136 [deg.] C. (removing the dry ice reheater), then cooled to room temperature, and the precipitated impurities are filtered off. After distillation of the volatile components from the filtrates, the crude desired sulfonyl isocyanate is recovered which can be purified by distillation under reduced pressure; boiling point 132 DEG to 138 DEG C. at 133 DEG to 146 DEG. The product is extremely sensitive to water, so it is important to avoid contact with air humidity carefully at work. Example 2

Isopropyl 1-2- (isocyanatosulfonyl) benzoate

To a solution of 60.7 g (0.25 mol) of isopropyl-2-sulfamoylbenzoate in 300 ml of anhydrous xylene is added 25.0 g (0.25 mole) of N-butyl isocyanate and 0.1 g, 4-diazabicyclo [2.2.2] octane, the mixture is heated under reflux to slowly stir phosgene for 2 hours.

The desired sulfonyl isocyanate is formed in the infrared spectrum (at 2 250 cm -1). The resulting cloudy solution is cooled to room temperature and decanted from a small amount of solid impurities. Removal of the volatile components from the decanted clear solution gives the desired crude sulfonyl isocyanate which can be used in the following reaction steps without further purification. Example 3 N- [(4,6-Dimethylpyrimidin-2-yl) aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide To a solution of 2-amino-4,6-dimethylpyrimidine (37 g) in anhydrous acetonitrile (500 mL) under stirring, 67 grams of 2-methoxycarbonylbenzenesulfonyl isocyanate are added. The reaction mixture was stirred 16 [deg.] C. and then the precipitated solid colorless product was filtered off; melting point 198 DEG-202 DEG C., the absorption maxima at 1,750, 1,700, 1600 and 1500 cirr1, which are in accordance with the predicted structure. Example 4 N- [Pyrimidin-2-yl] aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide

A solution of 2-aminopyrimidine (1.0 g) in dry acetonitrile (25 mL) was added to 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate at room temperature with stirring. The mixture was stirred for 24 hours and then the product was filtered off; 2.2 g of the desired product, m.p. 188 DEG -192 DEG C., are obtained. The product exhibits infrared absorption peaks at 1700, 1680 and 1580 cm-1, which are structurally N - [(pyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide. Example 5 N- (4-Methoxy-6-methylpyrimidin-2-yl) -aminocarbonyl] -2methoxycarbonylbenzenesulfonamide To a suspension of 1.4 g of 2-amino-4methoxy-6-methylpyrimidine in 30 ml of anhydrous of methylene chloride at room temperature with stirring was added 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate and the reaction mixture was stirred for 16 hours, then the unreacted startingamine is filtered off and the filtrate is distilled off under reduced pressure, at a temperature up to 40 ° C, solvent. The residue is stirred with 25 ml, the pH of the mixture is adjusted to 10 with 50% sodium hydroxide solution and the solution is filtered. The filtrate was acidified to pH 3 with hydrochloric acid, and the precipitated desired material was filtered off and dried, yielding 0.8 g of product, m.p. 173-179 ° C. The substance exhibits the infrared absorption maxima at 1720, 1680, 1630 and 1550 cm-1 which are consistent with the structure of N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] 2-methoxycarbonylbenzenesulfonamide. Example 6 N - [(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide The pH of the mixture is adjusted to 10 with 50% sodium hydroxide solution and the solution is filtered. The filtrate was acidified to pH 3 with hydrochloric acid, and the precipitated desired material was filtered off and dried, yielding 0.8 g of product, m.p. 173-179 ° C. The substance exhibits the infrared absorption maxima at 1720, 1680, 1630 and 1550 cm-1 which are consistent with the structure of N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] 2-methoxycarbonylbenzenesulfonamide. Example 6 N - [(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide The pH of the mixture is adjusted to 10 with 50% sodium hydroxide solution and the solution is filtered. The filtrate was acidified to pH 3 with hydrochloric acid, and the precipitated desired material was filtered off and dried, yielding 0.8 g of product, m.p. 173-179 ° C. The substance exhibits the infrared absorption maxima at 1720, 1680, 1630 and 1550 cm-1 which are consistent with the structure of N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] 2-methoxycarbonylbenzenesulfonamide. Example 6 N - [(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 1 630 and 550 cm-1 which are consistent with the structure of N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide. Example 6 N - [(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 1 630 and 550 cm-1 which are consistent with the structure of N - [(4-methoxy-6-methylpyrimidin-2-yl) aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide. Example 6 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 is stirred for 16 hours at room temperature under atmospheric pressure. The unreacted starting amine is filtered off and the solvent is distilled off under reduced pressure at a temperature of up to 40 ° C. The residue is stirred with 25 ml of water, the pH of the mixture is adjusted to 10 with 50% aqueous sodium hydroxide solution and the solution is filtered. The filtrate is acidified to pH 3, the precipitate is filtered off and dried; 1.7 g of product are obtained, m.p. 185-190 ° C. The substance exhibits infrared absorption maxima at 1700 and 1710 cm-1, which are consistent with the expected structure, and nuclear magnetic resonance absorption maxima at 3.8 and 3.85, which are in sequence with two different types of methoxy -group, which are simultaneously present in the product of this product. Example 7 2-Benzyloxycarbonyl-N - [(4,6-dimethylpyrimidin-2-yl) aminocarbonyl] benzenesulfonamide To 1.75 g of 2- (4,6- dimethylpyrimidin- 2- ylaminocarbonylsulfide amoyl] benzoic acid, a solution of 0.51 g of triethylamine in 10 ml of tetrahydrofuran and a solution of 0.88 g of benzyl bromide in 10 ml of tetrahydrofuran is added and the reaction mixture is heated to reflux for 1.5 hours, then filtered and the tetrahydrofuran is distilled off The residue is taken up in hot 1-chlorobutane, the solution is diluted with ethyl acetate and washed with water and saturated aqueous sodium bicarbonate, the organic layer is dried over anhydrous magnesium sulfate, the desiccant is filtered off and the solvents are distilled off under reduced pressure. Recrystallization of the residue from 1-chlorobutane affords the desired product of 157 ° C. The substance exhibits an infrared absorption mass at 1720, 1600 and 1560 cnr1, which are consistent with the expected ester structure, and the absorbance nuclear magnetic resonance maxima at 2.45 a, singlet, CH3; 5,3, singlet, CH 3 benzyl; 6,65 S, singlet, CH pyrimidine groups, and aryl moieties of 7 to 8 δ.

Following the procedure described in Examples 3 to 6, using equivalent amounts of 2-aminopyridinones and appropriately substituted sulfonyl isocyanates or isothiocyanates, the compounds of the formula I are prepared as shown in the following Table I.

Alternatively, according to the procedure described in Example 7, using equivalent amounts of the appropriately substituted benzoic acid derivatives and organic halogens, the compounds of the formula I in which R represents a group introduced by the action of an organic halide with a movable ha-logen. O

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6 g of 2-isopropoxycarbonylbenzenesulfonyl isocyanate dissolved in 5.0 ml of anhydrous methylene chloride. To quench the reaction, a small amount of unreacted 2-amino-4,6-dimethoxytriazine is filtered off, the methylene chloride is distilled off under reduced pressure and the residue is triturated with chlorobutane. 0.5 g of the desired product are obtained, m.p. 192-195 ° C. The substance exhibits infrared absorption maxima at 1705 and 1715 cm-1 which correspond to the structure of N - [(4,6-dimethoxy-1,3,5-triazin-2-yl] aminocarbonyl] -2- (isopropoxycarbonyl) onamide Example 11 N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2- (isopropoxycarbonyl) benzenesulfonamide To a solution of 26.8 g of 2- -methoxy-6-methyl-1,3,5-triazine in 300 ml of anhydrous methylene chloride was added a solution of 67, 0 g of 2-isopropoxycarbonylbenzenesulfonyl isocyanate in 100 ml of anhydrous methylene chloride is stirred at room temperature for 72 hours. The precipitated substance is filtered off and dried; 40.0 g of the desired product are obtained in the form of colorless crystals with a melting point of 193 DEG-196 DEG. The substance exhibits in-red absorption maximes at 1700 and 1710 cnv1 which conform to the structure of N - [(4-methoxy-6-methyl-1,3,5-triazim-2-yl) -aminocarbonyl] -2-isopropoxycarbonylbenzenesulfonamide. EXAMPLE 12 N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl] aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide The substance exhibits in-red absorption maximes at 1700 and 1710 cnv1 which conform to the structure of N - [(4-methoxy-6-methyl-1,3,5-triazim-2-yl) -aminocarbonyl] -2-isopropoxycarbonylbenzenesulfonamide. EXAMPLE 12 N - [(4,6-Dimethoxy-1,3,5-triazin-2-yl] aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide The substance exhibits in-red absorption maximes at 1700 and 1710 cnv1 which conform to the structure of N - [(4-methoxy-6-methyl-1,3,5-triazim-2-yl) -aminocarbonyl] -2-isopropoxycarbonylbenzenesulfonamide. EXAMPLE 12 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-1,3,5-triazine, 25 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonyl cyanate is stirred for 16 hours at room temperature. The unreacted amine is filtered off and the filtrate is distilled off the solvent under reduced pressure at a temperature up to 40 ° C. The residue is triturated with butyl chloride and the product is filtered off; the desired compound is obtained, melting above 170 DEG C. with decomposition. Example 13 N- [(4-Methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2methoxycarbonylbenzenesulfonamide To a suspension of 2-amino- -methyl-1,3,5-triazine in 25 ml of anhydrous methylene chloride is added with stirring at room temperature and at atmospheric pressure, 2.4 g of 2-methoxycarbonylbenzenesulfonyl isocyanate and the mixture is stirred for 16 hours. The undissolved portion is filtered off, the solvent is distilled off from the filtrate and the trituration is made with butyl chloride. The desired product is filtered off; a melting point of 165 ° C is obtained which has an absorption maximum at 1 550, 1 600, 1 680 and 1 700 cm -1 in the infrared range and in NMR at 2.5, 3.65 and 4.0 ppm with aromatic multiplet at 7.2 to 8 ppm.

By the methods described in Examples 8 to 13, using the equivalent amounts of the appropriate 2-amino-1,3,5-triazines and the correspondingly substituted sulfonylisocyanates or isothiocyanates, the compounds listed in Table II below are prepared. Example 14 N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] -2- (1 -methylpentyloxycarbonylbenzenesulfonamide To 1.5 ml of a 2M solution of trimethylaluminium , diluted with 5.0 ml of anhydrous toluene, was added dropwise a solution of 2-hexanol (0.61 g) in anhydrous toluene, under nitrogen, and the mixture was stirred for 15 minutes at room temperature and then 0.95 g of N- [(4-methoxy-6-methyl-1,3,5-triazin-2-yl] aminocarbonyl] -2methoxycarbonylbenzenesulfonamide. cooler, then cooled to room temperature and quenched by the careful addition of 20 ml of 10% hydrochloric acid. The organics were taken up in methylene chloride, the methylene chloride extract was washed with water, dried over anhydrous magnesium sulfate, filtered and the solvents were distilled off under reduced pressure. 0.65 g of the desired compound are obtained with a melting point of 125-130 ° C. The substance exhibits a characteristic absorption maximum in the in-red spectrum at 3,300, 1,725, 1,730, 1,585 and 1,555 cm-1. In Tables I and II, the compounds of the formula I in which the ester group R is a higher C5-C12 alkyl group can alternatively be prepared by the method described in Example 14 using equivalent amounts of the corresponding dialkylaluminium alcoholate and appropriately substituted lower alkyl ester of the present invention. Example 15 N - [(4,6-Dimethoxy-1,3,5-

A mixture of 4.2 g of methyl 2-sulfamoylbenzoate, 4.0 g of 4,6-dimethoxy-2-isothiocyanato-1,3,5-triazine, 2.7 g of anhydrous carbonate and 70 ml of acetone was stirred heating at 40 ° C; after 2 hours, a precipitate is precipitated out. The reaction mixture is stirred for three more irrins at room temperature, then the precipitate is filtered off, suspended in 150 ml of water and adjusted to pH 2. The desired product is filtered off, washed with water and dried. 4.8 g of a melting point of 165-170 ° C are obtained, which shows the infrared absorption maxima at 1760, 1650 and 1600 cm-1, and the nuclear magnetic resonance maxima for the methoxy groups at 4.0 and 3 , 8 (singlet), and 8.0 to 8.7 (multiplet) which are in agreement with the structure of the desired product.

By the method described in Example 15, employing equivalent amounts of the appropriate isocyanatopyrimidine or triazine and the appropriately substituted benzenesulfonamide, compounds of general formula I wherein W is sulfur may be prepared. 281852

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Following the procedure described in Example 17, employing equivalent amounts of the appropriate 4-aminopyrimidines and appropriately substituted sulfonylisocyanates or isothiocyanates, the compounds listed in Table IV below are prepared.

Table IV

<img img-format="tif" img-content="drawing" file="CS261852B2D00511.tif" id="idf0073" />

QR r3 Rs W Xi Yj och3 HH 0 OCHa ch3 och3 HH 0 ch3 och3 oc2h5 6-Ci H 0 och3 OCH3 och3 3 -C1 5-C 10 OCH3 C2H5 och3 5-OCH3 H3 og3 och3 och3 5-NO2 3- C1 0 OCH3 CH2 ogh3 OC2H5 5-C1 Ή 0 OCH3 OCH3 OCH2CH2Cl HH 0 OCH3 OCH3 O (CH2CH2O) 2CH3 HH 0 OCH3 OCH3 O-CHCH 3 H Ή 0 OCH3 OCH3 CH3 OCH2CH2Br HH 0 IC1 OCH3 OCH2CF3 HH 0 OCH3 OCH3 o ch2chch3 0 HH OCH3 CH3 CH3 O (CH2) 4CH3 OCH3 OCH3 HH 0 ochch2ch3 H OCH3 OCH3 Ή 0 1 0 CH2CH3 och2chch2ch3 HH OCH3 CH3 OCH3 OCH CH CH HH CH3 CH3 0 CH3 ogh3 OCH2CBr3 HH 0 OCH3 OCH3 OCHCH2C1 Ή H OCH3 OCH3 0

CHF 261852 53 54

Using the appropriate N - [(triazinyl) aminocarbonyl] -2-carbonylbenzenesulfonamides or N - [(pyrimidinyl) aminocarbonyl] -2-carbonylbenzenesulfonamides as starting materials, the compounds of formula I listed in Table V are prepared.

For example, the compound of Example 12 can be converted into the N - [(4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2-methoxycarbonyl- N -methylbenzenesulfonamide by the methylation shown in reaction equation 2.

The following procedure is followed: An equimolar amount of sodium hydride (50% dispersion in mineral oil) is added to a solution of the compound described in Example 12 in dimethylformamide. When hydrogen evolution ceases, an equivalent amount of dimethyl sulfate is added. The reaction mixture is stirred for 2 to 18 hours, poured into a large volume of water and the precipitated product is filtered off.

Table V - and H. N- with R.

<img img-format="tif" img-content="drawing" file="CS261852B2D00521.tif" id="idf0074" />

* 1 -, -C = 3 RS

HO-C qRII QR R2 R3 R5 XY HHH OCH3 CH3 CH3 OCH3 OCH3 HH CH3 CH3 0 II-HHH-C3H7 CH3 CH3 C3H7 0-1-OCH3 OCH3 OCH3 HHH HH CH3 CH3 OCH och2ch2och3 and 5-C1 6-C1 H CH3 OCH2CH3 O (CH2CH2O) 2CH3 3-C1 HH OCH3 CH3 O (CH2) 4 CH = CH 2 HHH OCH3 CH3 OCH2CF3 HHH OCH3 CH3 O (CH2) 4GH3 HHH CH3 CH3 och2chch2ch3 HHH OCH3 OCH3 CH3 O-CHCH 3 HHH OCH3 CH3 1 j CH3 CH3 1.1 Found: C, 261852;

<img img-format="tif" img-content="drawing" file="CS261852B2D00531.tif" id="idf0075" />

7-CN-3-N-methyl-3-methyl-2-oxazolidinone, (CH 3) 2 N-OCH 3, CH 3 CH 3 CH 3 OCH 3 CH 3 OCH 2 CH 3 OCH 2 CH 3 OCH 2 CH 3 OCH 3 OCH 3 OCH 3 CH HHH CH3 CH3 CH3 O (CH2) 4CH3 HHH OCH3 OCH3 ochch2ch2ch3 HHH CH3 CH3 CH3 OCHCHaCHa HHH OCH3 OCH3 CH2CH3 OCH9CHCH2CH3 "1 HHH CH3 CH3 CH3 OCH-CH 3 HHH CH3 CH3 CH3 CH3 OCHaCBra HHH CH3 CH3 OCHCH2C1 1 CH2F HHH OCH CH3 261 852 95 56

The compounds of general formula (I) shown in Table VI are prepared as described in Reaction Scheme 5 using appropriately substituted isobutyl-N-alkylbenzenecarbamoyl chloride or thiocarbamoyl chloride and the corresponding aminopyrimidine or aminotriazine as the reactants. For example, N- [N- (4-methoxy-6-methylpyrimidin-2-yl) -N-methylaminocarbonyl] -2- methoxycarbonyl- N -methylbenzenesulfonamide was prepared by adding to a solution of 3.0 grams of N - [(2-methoxycarbonylphenyl) sulfonyl] -N-methylcarbamoyl chloride in 50 ml of tetrahydrofuran is added 1.0 g of triethylamine and 1.5 g of 2-methylamino-4-methoxy- for several hours to boil under the back cooler. The precipitated salt is filtered off and the solvent is distilled off the filtrate; the evaporator is the above-mentioned product.

Table VI - aX

<img img-format="tif" img-content="drawing" file="CS261852B2D00541.tif" id="idf0076" />

QR r2 r3 W r5 XY och3 HH with ch3 och3 och3 ogh3 HH with H ch3 ch3 och3 6-CH3 H0 ch3 och3 OCH2CH2, COOCH. O (CH 2) 9 CH 3 HH O H OCH 3 O (CH 2) 4 CH = CH 2 HH O H OCH 3 and OCH 2 CH 2 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CHCH 3 HH 0 H ch3 ch3 ch3 ochch2ch3 HH 0 H ch3 ch3 ch2ch3 OCH2CHCH2CH3 HH0H ch3ch3 ch3 OCH-CHCH3 1 | HH 0 H ch3 ch3 ch3 ch3 OCH2CBr3 HH 0 H ch3 ch3 OCHCH2C1 HH 0 H ch3 ch3 ch2f och2ch2f HH 0 H och3 och3 OCH2CC13 HH 0 H och3 OCHg 261852 57 58

Table VI-b

<img img-format="tif" img-content="drawing" file="CS261852B2D00551.tif" id="idf0077" />

(CH 2 CH 2 O) 2 CH 3 HH 0 H (CH 2) 3 CH 3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 3 OCH 2 OCH 3 OCH 3 O OCH3 OCH3 O (CH) 4 CH = CH2 HH 0 H OCH3 OCH3 O-ch2chch3 HH 0 H OCH3 OCH3 CH3 O (CH2) 4CH3 HH 0 H OCH3 OCH3 ochch3ch3 HH 0 H CH3 CH3 CH2CH3 och2chch2ch3 HH 0 H OCH 3 OCH 3 CH 3 O-CH 3 1 | HH 0 H och3 och3 ch3 ch3 OCH2CBr3 HH 0 H och3 och3 OCHCH2C1 HH 0 H och3 OCH3 ch2f OCHaCF3 HH 0 H och3 och3 Example 18 kladu. The Nuclear Magnetic Resonance Spectrum shows apparent maxima for 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 a 50% aqueous solution of sodium hydroxide is heated on a boiling water bath with shaking 40 ml of water is added and heating and shaking is continued for half an hour, the solution is filtered, the filtrate is acidified to pH 2 with hydrochloric acid and the precipitate is filtered off and dried, yielding 0.7 g of the title compound melting at 160 DEG C. for dimethyl groups on the pyrimidine ring of 2.6 ppm and for aromatic hydrocarbons of 7.2 and 8.4 ppm. The absence of the resonance peak at 4.0 ppm confirms the conversion of the methyl group to the carboxyl group.

By the method of Example 18, using the appropriate N - [(triazinyl) aminocarbonyl] -2-alkoxycarbonylbenzenesulfonamides or N - [(pyrimidinyl) aminocarbonyl] -2- formula I shown in Table VII, 261832

Table VII -a

<img img-format="tif" img-content="drawing" file="CS261852B2D00561.tif" id="idf0078" />

R 3 R 4 R 5 WXYHHHH 0 CH 3 OCH 3 6 -Cl H CH 3 H 0 OCH 3 CH 2 OCH 3 6 -C1 HHHS OCH 3 CH 3 3 -Cl 5 -Cl HHSOCH 2 N (CH 3) and VII -b

Table

<img img-format="tif" img-content="drawing" file="CS261852B2D00562.tif" id="idf0079" />

r2 r3 r4 R5 WXYHHHH 0 CHa OCH3 HHHHS OCH3 OCH3 4-C1-6-C1 HHO OCH2 OCH2 CH3

Table VII-c

<img img-format="tif" img-content="drawing" file="CS261852B2D00563.tif" id="idf0080" />

Table VII - d

<img img-format="tif" img-content="drawing" file="CS261852B2D00564.tif" id="idf0081" />

The substance exhibits NMR absorption maxima at 2.5 ppm (methyl groups on the pyrimidine ring), 2.85 and 3.1 ppm (non-equivalent of the dimethyl amido groups), 6.8 ppm (pyrimidine ring hydrogen) and 7.2 up to 8.4 ppm (aromatic hydrogens). Example 20 N - [(4,6-Dimethoxypyrimidin-2-yl) aminocarbonyl] -2-isopropylaminocarbonylbenzenesulfonamide To a solution of 4.5 g of N - [(4,6-dimethoxypyrimidin-2- ] -2-methoxycarbonylbenzenesulfonamide in 75 ml of methylene chloride at room temperature with stirring is added a solution of 1.44 g of dimethylaluminium isopropylamide in 37 ml of methylene chloride. The reaction mixture is heated to reflux under reflux and then distilling off methylene chloride while adding anhydrous toluene until the temperature of the mixture reaches 100 ° C. The reaction mixture was heated at 100 ° C for two hours, then the solution is cooled and treated with 10 ml of methanol. The solvents were distilled off under reduced pressure, the residue was triturated with a mixture of methanol, water and dilute hydrochloric acid and the product was taken up in methylene chloride from the aqueous suspension obtained. Organic extracts are distilled off with methyleneciloride and the solid residue (4.28 g) is triturated with 1-chlorobutane. 2.0 g of pure product, m.p. 148-150 ° C, gave a single spot on silica gel (1: 1 acetonide-hexane, Rf 0.34) and showed an absorption maxima in the NMR spectrum 1,15, 4,0, 3,8-4,3 and 7,5-8,2PPm. Organic extracts are distilled off with methyleneciloride and the solid residue (4.28 g) is triturated with 1-chlorobutane. 2.0 g of pure product, m.p. 148-150 ° C, gave a single spot on silica gel (1: 1 acetonide-hexane, Rf 0.34) and showed an absorption maxima in the NMR spectrum 1,15, 4,0, 3,8-4,3 and 7,5-8,2PPm. Organic extracts are distilled off with methyleneciloride and the solid residue (4.28 g) is triturated with 1-chlorobutane. 2.0 g of pure product, m.p. 148-150 ° C, gave a single spot on silica gel (1: 1 acetonide-hexane, Rf 0.34) and showed an absorption maxima in the NMR spectrum 1,15, 4,0, 3,8-4,3 and 7,5-8,2PPm.

Found: C, 48.1; H, 5.20; N, 16.0%. Found: C, 48.7;

Using the procedure described in Examples 19 and 20, by reacting equivalent amounts of the appropriately substituted dialkaluminum N-alkylamides with the appropriately substituted esters of the present invention, the compounds of formula (I) listed in Table VIII are prepared. 261852 uo oco Cv

cOCO CO

CM

O in σ&gt;

CO OOOOO CO CO L LO CO CO CO rH rH II rH ¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¿¨ fo ío «

O'jhl | HH H H M W WHH FM FM FM Mt hM FM gguooou ¢ 0

X what do what what ►fi h- (I-Ťt eo * "co co&gt; r &lt;OOOgoggoooououuo what what what

CO cot-rt Hrt CO hrt tH * -M llt tT * 1 OH HM T1 * * · · gg o ooooo uuoo ° oo o

Table VIII

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US

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hf-tl-i-tMO1-H1-KMKH

►M (JLi fM &lt;| ± 4 FM H- |

FM FM FM FM FM FM FM FM FM FM

FM MM for FM. FW MM FM, FM FM us ht t-ffi t? - g

X &lt;L

The US US $ 40,000 in US $ 5,000

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04 261852 o 0 + - * 4-Í X!

□ SSoO ° ° O co

X ao

CM

CD

rH

CM

CM co X X co x X X X X X X X X X XX o tM C o Ooooooo O o oooooom mm mm KEKK xo o oo oo

£ «X5 gg» ® X o XXXX XXX X xxxx XXXX XXX X xxxx XXXX XXX X xxxx XXXX XXX X xxxx XXXX XXX X

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what

X o

10: £ o

X? -i? -u

X o 00 cc eE,% X Xu-o

<img img-format="tif" img-content="drawing" file="CS261852B2D00592.tif" id="idf0085" />

261832 c ^. i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i i r 1 in cn 1 o! CM 1 1 cm in t co CO-i-r i r r r r r i i i i i i i i i i i i i i i i i i ii i i i i i i i i i ii 4-1 4η 5 q ο ω ο ο ο ΟΟ 00 C0 00 00 00 Μη ΟΟ ΜΗ μη Μ '· μη 4η μη μη 4η 4η 4η u * ** CS uouuoo υ ο 00 μη οο4η μη ο ο ° Fri-1 Η 1-rt HM M HH H-1 MH H 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th 4th

<img img-format="tif" img-content="drawing" file="CS261852B2D00601.tif" id="idf0086" />

IIIII E H4 M4 M4 ML CO

In a preferred embodiment of the present invention there is provided a co-substituted substituent co- co 7 &lt;n1 b what co

Table VIII

<img img-format="tif" img-content="drawing" file="CS261852B2D00611.tif" id="idf0087" />

Pi Pi 2 &amp; lftS2 cn o M5 x o5% ooogogoiu co CO CO co

Xuggugyoo y - owoo «¢ 0

5S oo

'EEEEEEE kkkxeke

X ffi XX ffi KK Pi Pi Pi

HMH HHHH HHHMHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHMH

WHAT

M m O D M M tH (I tM ​​H- |

LO o

&lt;M

CM

I ts S E Co E X X O O o O o í d

CM

O

rh |

® XXXX K ou 2 wo OO ooo

<img img-format="tif" img-content="drawing" file="CS261852B2D00612.tif" id="idf0088" />

"X E.Xg (3? X:

XX XX X

X 'EXX · E

E: EXX-X

EE EXE

EE ^ EG «RH Hrt

¿¿¿¿¿¿-

Xu - Pi Pi Pi Pi Pi 261852 o

N

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X

O o

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O

&lt;N

such as OxyuOOOOOQOQOOO

X X CO CO X ooooooo O co lj '. "y yyyyy yyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy

KXXftKKXX X% X%

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KXXXKXXX X fft

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ffiXXXXXXX X XX xxxxxxxx (_,&gt; _4 t_ | 4-1 4h 4- &lt;HOOX x5 o «P ^ X - * * 5gs? ii X ^ XXXXU«

D? X, Xx, «SST! AND

CO ffi WJ JT &lt;3) ¾ c «5

X 4 «&lt;-&gt;&gt;

&lt;N

X o X! O-u

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261852

<img img-format="tif" img-content="drawing" file="CS261852B2D00631.tif" id="idf0091" />

denotes the substituent 81 together

Table VIII -c 281852 82

Ra

<img img-format="tif" img-content="drawing" file="CS261852B2D00641.tif" id="idf0092" />

Xi

H CH3 CH3 CH3 C2 H5 sec-C4 H9

H

H 5-Cl 6 -Cl

H

H

H

H

H

H

H

H

O

Osoo

H

H

H

H

H

H3 CH3 OCH3 CH3 CH3 CH3 CH3 and OCH3 CH3 CH3 CH3

Table VIII -d

<img img-format="tif" img-content="drawing" file="CS261852B2D00642.tif" id="idf0093" />

CH3H C3H5 5-Cl

EXAMPLE 21 N- [(4-Methoxy-6-methyltriazin-2-yl) aminocarbonyl] -2- (methylthio) carbonylbenzenesulfonamide N- [ -6-methyl-1,3,5-triazin-2-yl) aminocarbonyl) -2- (n-butylthio) carboinylbenzenesulfonamide To 15 ml of anhydrous toluene was added dropwise via syringe with trimethylaluminum , 0 ml of 2M solution) and 3.8 g of N - [(4-methoxy-6-methyltriazin-2-yl) aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide are added in portions.

The reaction mixture is stirred for one hour at room temperature, and then the methylmercaptan gas is added to the solution until the temperature which begins to rise begins to fall; then the mercaptan intake is set. The reaction mixture was stirred for 1 hour at room temperature and then quenched with 25 ml of 10% hydrochloric acid. The resulting white suspension is filtered off; 2.9 g of a colorless solid product having an in-red absorption maximum at 1740 and 1690 cnr1 which are consistent with the structure of N - [(4-methoxy-6-methyltriazin-2-yl) aminocarbonyl] -2- (methylthio) carbonyl-benzenesulfonamide. To 1.5 ml of anhydrous toluene is added dropwise 1.5 ml of a 2M solution of trimethylaluminium in a nitrogen atmosphere and then another 0.54 g (0.006 mol) of n-butanethiol dissolved in 2.0 ml of toluene is added dropwise. To the slurry is added in portions 0, 95 g of N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbamoylbenzenesulfonamide and the mixture was heated at 80 ° C for 3 hours. After cooling to room temperature, the reaction mixture is quenched with 25 ml of 10% hydrochloric acid, the product is taken up in methylene chloride, the organic extract is dried over anhydrous magnesium sulfate, the precipitate is filtered off and the solvent is distilled off. The crude oil residue is triturated with hexane 0 , 6 g of a colorless substance having a melting point of 115-120 ° C. The substance exhibits infra-red absorption peaks at 1,725, 1,680, 1,600 and 1,560 cm-1, which are in agreement with the sister N - [(4-methoxy-6-methyl- 2-yl-aminocarbonyl] -2- (n-butylthiocarbonylbenzenesulfonamide) Example 23 N - [(4- methoxy- 6 -methyl- 1,3,5- triazin- 2- yl- aminocarbonyl- 2-isopropylthiocarbonyl-benzenesulfonamide To a solution of 1, 5 ml of 2N trimethylaluminum in 5 ml of toluene was added dropwise 0.48 g (6.0 mmol) of 2-propanethiol dissolved in 2 ml of toluene. The obtained aluminum compound is stirred for 15 minutes at room temperature and then thereto is added in one portion 0.95 g (2.5 mmol) of N - [(4-methoxy-6-methyl-1,3,5- 2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide The suspension is heated for 3 hours at room temperature, then cooled to room temperature and 10% hydrochloric acid (15 ml) is added and the mixture is stirred The precipitated solid was filtered off, washed with hexane and air dried to give 0.4 g of the desired product, m.p. 155 DEG-158 DEG C. The infrared absorption spectrum of the substance was in agreement with the N-terminal esters of N- [(4-methoxy-6-methyl-1,3,5-

By the procedures described in Examples 21 to 23, using the equivalent amounts of the appropriately substituted dialkylaluminum alkyl thioates and the corresponding substituted esters of this invention, the compounds of the formula I listed in Table I are prepared.

<img img-format="tif" img-content="drawing" file="CS261852B2D00651.tif" id="idf0094" />

WN / 'QR r3 r3 W Rs XY 1.1., C3 sch3 HHOH ch3 o, ch3 sch3 HHOH ch3 ch3 sc2h5 HHOH och3 och3 S-n-CrH2bHHOH och3 och3 schch3 HHOH och3 ch3 143-146 ch3 SCHCH2CH3, | HHOH ch3 ch3 ch3 SCH (CH2) 9CH3 HHOH och3 och3 1 ch3 schch2ci ch3

SCH (CH 2) 2 CH 3 H;

O-S-H HO

-S-NH 2 H OH OCH 3 CH 3 H OCH 3 CH 3 H CH 3 H OCH 3 CH 3 CH 3 133-136

X

Y 1.1 ° C

QR

Ra 261852 R3 W R5 S-CHCH2 CHBr] CH3 S-CHCH2 CCl3

<img img-format="tif" img-content="drawing" file="CS261852B2D00661.tif" id="idf0095" />

H

H

H

H

H

H

H

H 0 0 0 0

H

H

H

H ch3 ch3 ch3 ch3 ch3 ch3 och3 och3 gh3 o-

<img img-format="tif" img-content="drawing" file="CS261852B2D00662.tif" id="idf0096" />

OCHZ H

H

H-ss (ch2) 2ch3

H

H

H

H

H

, H

H

H

H

H

H 0 0 0 0 0

O 0

H

H

H

TO

H

H

H ch3 gh3 ch3 ch3 och3 och3 OCH3 CH3 148-150 och3 ch3 ch3 ch3 ch3 ch3 ch3 201352

Table IX -b

<img img-format="tif" img-content="drawing" file="CS261852B2D00671.tif" id="idf0097" />

H

H

H

H

H

H

H

H

O

O

O

O

H

H

H

H 0CH3 0CH3 0GH3 OCH3 OCH3 OCH3 CH3 0CH3 115-120; sc2h5S Cr.HnS-n-n-n-C8H17S C4Ho

<img img-format="tif" img-content="drawing" file="CS261852B2D00672.tif" id="idf0098" />

-o-O S (CH2) 8CH = CH2 SCHCH, I, CH3 -schch2ch3ch3 -SCH (CH3) 9CH3ch3 -SCHCH2C1ch3 _SCH (CH2) 3 Cl CH2C1 H3 Ί

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

H

O

O

O

O

O

O

O

O

Ooo O CH3 OCH3 OCH3 CH3 OCH3 CH3 H 0CH3 CH3 H 0CH3 0CH3 H CH3 CH3 CH3 OCH3 OCH3 OCH3 CH3 H 0CH3 CH3 CH 177-178 ·! CH 3, CH 3, CH 3, CH 3,

<img img-format="tif" img-content="drawing" file="CS261852B2D00681.tif" id="idf0099" />

s-O-O 3 -SO 3,

&amp; Quot; S-CH &amp; quot; CH,

-SCH

S ~ CH C © 1

<img img-format="tif" img-content="drawing" file="CS261852B2D00682.tif" id="idf0100" />

sch2 ~ ^

SCH 261832

Ra R3 W Rs XYHH 0 H ch3 ch3 HH 0 H ch3 ch3 HH 0 H ch3 ch3 HH 0 H ch3 ch3 HH 0 H ch3 ch3 HH 0 H ch3 ch3 HH 0 H och3 ch3 HH 0 H ch3 ch3 HH 0 H ch3 gh3 HH 0 H CH 3 CH 3 γ 1.1, ° C 2818 S2

Table IX -c

QR

<img img-format="tif" img-content="drawing" file="CS261852B2D00691.tif" id="idf0101" />

-SCHCH3CH3CH2CH2. CH3 -SCH2CH2-, -S-CHCH2CCl3CH3

H

H

II O CH3 CH3 O OCH3 CH3 OCH3 ch3 ch3 ch3 ch3 ch3

<img img-format="tif" img-content="drawing" file="CS261852B2D00692.tif" id="idf0102" />

-CH3 -CH3-

-S-CHCH / C13

H

H

H

H

H

H

H

H

O

O

O

OCH3 OCH3CH3CH3CH3CH3CH3CH3CH3 -CH3 -S-n-C5H11OCH3 OCH3 O OCH3 OCH3

H

H 261852 63

Agronomically useful formulations containing the active ingredient of the compound of formula I can be prepared in conventional manner. Said compositions can be manufactured in the form of dusts, granules, pellets, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these preparations can be applied directly. Spraying preparations are used in a quantity of from a few liters to several hundred and sixty-five liters per hectare prior to application to the environment and diluted spraying solutions. The agricultural preparations according to the invention generally contain about 0.1 to 99% by weight of the active ingredient (s) and at least one of the following adjuvants: a) about 0.1 to 20% % of the surfactant (s) and (b) about 1 to 99.9 wt. (S) of solid or liquid diluent (s).

Table X

Active Agent Thinner (a) Surfactant (a)

Wet Dusts 20-90 0-74 1-10 Oil Suspensions and Emulsions 3-50 40-95 0-14 (including Emulsifiable Concentrates) Water Suspensions 10-50 40-84 1-20 Dusts 1-25 70-99 0-5 Granules and Pellets 0.1-95 5-99.9 0-15

Note: The active substance together with at least one excipient (surfactant / diluent) is equal to 100% by weight. In the compositions according to the invention, there may of course be less or greater amounts of the active ingredient, according to the intended use and the physical properties of the compound of the formula I. Sometimes, the higher the surfactant ratio to the active compound; this can be achieved by adding a surfactant either to the preparation or to a mixing tank in a spray solution. Some typical solid diluents suitable for preparation of agricultural products according to the invention are described in Watkinse et al., Handbook of Insectic Dust Diluents and Carriers, 2nd Edition, Dorland Books, Galdwell, New Jersey, alleles of other solids, either extracted from natural resources, or artificially grown. More softener diluents are more suitable for wetting dusts, more compact are more suitable for dusting.

Typical liquid diluents and solvents are described in Marsden's "Solvent Vents Guide", 2nd Edition, Interscience, New York, 1950. The solubility of the active compounds below 0.1% is suitable for the preparation of suspension concentrates; in the preparation of concentrated solutions preference is given to solutions that are stable and do not separate into single phases at standing at 0 ° C.

Surfactants and their doped use are summarized in the Handbook of Detergents and Emulsifiers, MC Publishing Corp., Ridgewood, New Jersey, and in the encyclopedia of Sisely et al., "Encyclopedia of Surface Active

Agents &amp; quot ;, Chemical Publishing Co., Inc., New York, 1964. All the compositions of the invention may additionally contain small amounts of other additives, such as foaming, sintering, corrosion, microbial growth, and the like.

The processes for the preparation of these preparations are well known to those skilled in the art. The solutions are prepared simply by mixing the ingredients together. Gently powdered solid preparations are usually manufactured by mixing ammonia components, for example in a hammer mill or a fluidized microniser. Suspensions are prepared by grinding the wet components (seeLittler, U.S. Patent 3,060,084). Granules can be produced either by spraying a melt or suspension of a substance onto a pre-prepared granular carrier or by suitable agglomeration techniques such as, for example, Browning's "Agglomeration", Chemical Engineering, 4th edition, 1967, p. 147 et seq. and Perry's Manual "Perry's Chemical Engineer's Handbook", 4th Edition, McGraw-Hill, New York, 1963, pp. 8-59 et seq.

Further information concerning the method for formulating herbicidal compositions is provided, for example, in the following literature: M. Loux, U.S. Pat. No. 3,235,361, Column 6, Line 16 to Column 7, Line 19, and Examples 10 to 41. RW Luckenbaugh, U.S. Pat. No. 3,309,192, Col. 5, Line 43, to Column 7, line 62 and examples 8, 12, 15, 39, 41, 52, 261852, 87, 53, 58, 132-140, 162-164, 166, 167, 169-182. H. Gysin and E. Knusli, U.S. Patent 2,891,855, Column 3, Line 66, Column 5, Line 17, and Examples 1-4. GC Klingman, &amp; quot; Weed Control as &amp; Sci. &amp; Quot ;, John Wiley Sons, Inc., New York, p. 81-96. JD Fryer and SA Evans, "Weed Control Handbook", 5th. Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103. In the following exemplary embodiments, all parts, unless otherwise indicated, denote parts by weight. Example 24

Wet Dust N - [(4,6-Dimethoxypyrimidin-2-ylaminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 95% sodium dioctyl sulfosuccinate sodium 0.1% sodium lignin sulfonate 1% synthetic fine silica 4%

The components are blended and the mixture mixed with the hammer mill to yield almost all particle sizes at 100 microns. The ground material is sieved through a USS No. 50 sieve and filled into suitable containers. Example 25

Granule wetting powder of Example 24 10% granular attapulgite screened over USS screen No. 20-40, size 0.84-0.42 mm) 90%

The wettable powder suspension described in Example 24, containing 50% of the solids, is sprayed onto the surface of the granulated tap water with stirring in a twin-screw mixer. The granules are dried and filled into suitable containers. Example 26

Wetting powder N - [(4-methyl-6-methoxy-1,3,5-triazin-2-yl) aminocarbonyl] -2methoxycarbonylbenzenesulfonamide 40% sodium dioctyl sulfosuccinate sodium 1.5% sodium lignin sulfonate 3 % methylcellulose of low viscosity 1.5% attapulgite 54% 68 meter 0.3 mm) and then filled into suitable volumes. Example 27

Granule wetting dust from example 26 25% gypsum 64% potassium sulphate 11%

The individual components are mixed in a rotary mill and the mixture is sprayed with such amounts to granulate. When granule size reaches a diameter of 1.0 to 0.42 mm (USS screen number 18-40), the granulate is removed, dried and sieved. The material that remains squeezed is crushed to obtain a further portion of the size of the grain. A granule containing 10% of the active substance is obtained. Example 28

Wettable dust N / - [(4,6-dimethoxy-1,3,5-triazin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 65% dodecylphenyl ether polyethylene glycol 2% sodium lignin sulfonate 4% sodium aluminosilicate 6% montmorillonite ) 23%

The solids are thoroughly mixed and the liquid surfactant is sprayed onto the mixer in the mixer. The stirred material is then milled in a ball mill so that almost all the particles have a particle size of less than 100 microns. re-blends, sieves USS No. 50 (0.3 mm diameter holes) and fills into suitable containers. Example 29

O-suspension of N- [(4-methyl-6-methoxypyrimidin-2-yl) aminocarbonyl] -2- methoxycarbonylbdene sulfonamide 25% polyoxyethylene sorbitol hexaoleate 5% oily higher aliphatic hydrocarbon 70%

The individual components are ground together with the mixing ball to the sand so that the particle size drops below about 5 millimeters. The suspension obtained can be applied directly but more preferably after dilution with a suitable oleic diluent or after emulsification. Example 30

An aqueous suspension of N - [(4,6-dimethyl-1,3,5-triazolo-2-yl) -

The individual components are thoroughly mixed and milled in an air micronizer so that the average particle size is below 15 microns. The ground material is re-mixed, sieved through a No. 50 mesh U.S. sieve through a 25% 261852 70 69 aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 25% hydrated attapulgite 3% hydrated attapulgite 3% calcium ligninsulfonate 10% sodium dihydrogen phosphate 0, 5% water 61.5%

The individual components are ground together in a ball or roller mill so that the particle size of the particles drops below 10 microns and the slurry is filled into suitable volumes. Example 31

Extruded pellets N - ((4,6-dimethylpyrimidin-2-yl) aminocarbonyl] -2-methoxycarbonylbenzene sulfonate 25% Anhydrous sodium sulfate 10%

The ingredients are mixed, ground in a hammer mill and then moistened with about 12% water. The material is then extruded in the form of a cylindrical rod of about 3 mm in diameter, which is cut into pellets of up to 3 mm length. The pellets may be used directly after drying, or they can be crushed to pass through a SSS 20 mesh (0,84 mm / min.). The USS No. 40 retained granules (0.42 mm mesh openings are filled into suitable containers and the finer finer material is recycled

A solution of N- (4,6-dimethoxy-1,3,5-triazin-2-yl) aminocarbonyl [-2-methoxycarbonylbenzenesulfonamide 5% dimethylformamide 95% . The solution obtained is to be used in small volumes. Example 33

Wettable dust N - [(4,6-dimethylpyrimidin-2-yl) -aminocarbonyl] -2-methoxycarbonylbenzenesulfonamide 80% sodium alkylnaphthalenesulfonate 2% sodium ligninsulfonate 2% synthetic amorphous silica 3% kaolinite 13% less than 100 microns. The ground material is remixed, sieved through USS No. 50 and filled into suitable containers.

The compounds of formula I are highly effective herbicides. They may be used as broad-spectrum herbicides for pro-emergence and / or post-emergence weed propagation in areas where complete vegetation is desirable, such as the vicinity of storage tanks for feedstocks, ammunition depots, industrial floor areas, oil wells, -tracks theaters for motorists, billboards around, road and railway constructions. At a suitably chosen dose and time of application, the compounds of formula (I) may also be used for the beneficial modification of plant growth and for the selective control of weeds of crop plants such as wheat and barley. The exact amount of the compounds of the formula I to be used in the given situation depends on the desired end result, the intensity of foliage of the plants, the weight of the weed to be extinguished, the type of crop, the type of soil, the type of product used, the mode of application, the weather conditions and other factors. Due to the fact that many different variables are applied to the application, it is not possible to determine the application dose suitable for all situations. In general, the compounds of formula I can be applied at rates in the range of about 0.005 to 20 kg / ha, preferably in the range of 0.125 to 10 kg / ha. Generally, higher dosages of this range are used under unfavorable conditions, or when the duration of action in soil has to be prolonged, and lower doses are selected for selective weed control of crop plants. on weather conditions and other factors. Due to the fact that many different variables are applied to the application, it is not possible to determine the application dose suitable for all situations. In general, the compounds of formula I can be applied at rates in the range of about 0.005 to 20 kg / ha, preferably in the range of 0.125 to 10 kg / ha. Generally, higher dosages of this range are used under unfavorable conditions, or when the duration of action in soil has to be prolonged, and lower doses are selected for selective weed control of crop plants. on weather conditions and other factors. Due to the fact that many different variables are applied to the application, it is not possible to determine the application dose suitable for all situations. In general, the compounds of formula I can be applied at rates in the range of about 0.005 to 20 kg / ha, preferably in the range of 0.125 to 10 kg / ha. Generally, higher dosages of this range are used under unfavorable conditions, or when the duration of action in soil has to be prolonged, and lower doses are selected for selective weed control of crop plants.

The combination of the compounds of the formula (Igs) with known herbicides also allows for the effective control of weeds in crops such as wheat or barley. Typical herbicides that can be used in combination with the compounds of formula I are, for example, chlorine toluron [3- (3-chloro-4-methylphenyl) -1,1-dimethylurea], MCPP [ - [4-chloro-2-methylphenoxy] propanoic acid], methoxuron [3- (3-chloro-4methoxyphenyl) -1,1-dimethylurea], methabenzthiazuron [1- 1,3-dimethylureas], dichlofop {[methyl 2- (4- (2,4-dichlorophenoxy) phenoxy] propanoate], tri-allyl [S- 2,3-dichloroallyl diisopropylthiocarbamate]

The individual components are thoroughly mixed and the mixture ground on a hammer mill so that almost all the particles have the size of isoproturon [3- (4-isopropylphenyl) -1,1-dimethylsulfuron] or dienzoquat [1,2-dimethyl- 3,5-diphenylpyrazolium ion].

The compounds of formula (I) may also be combined with other herbicides; particularly preferred are combinations with ureas such as 3- (3,4-dichlorophenyl) -1,1-dimethylurea, 3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea and 1,1-dimethyl-3- (α, α, α-trifluoro-m-tolyl) urea; striasins such as 2-chloro-4- (ethylamino) -6- (isopropylamino) -s-triazine; with so-called 5-bromo-3-sec-butyl-6-methyluracil; with N- (phosphonomethyl) -glycine with 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4- (1H, 3H) -dione with N, N-dimethyl-2,2-diphenylacetamide; with 2,4-dichlorophenoxyacetic acid (with closely related compounds) with 4-chloro-2-butynyl-3-chlorophenylcarbamate with diisopropylthiolcarbamic acid S- (2,3,3- -benzoyl-N- (3,4-dichlorophenyl) -2-aminopropionate, 4-amino-6-tert-butyl 3- (methylthio)

The herbicidal activity of the compounds of general formula I was found in a number of assays carried out in the glasshouse and on the fields. The tests and results obtained are described below. The herbicidal activity was evaluated using a numerical scale ranging from no effect to up to 10 maxima. The accompanying descriptive symbols include the following meanings: C · chlorosis or necrosis) · defoliation E = inhibition of germination G suppression of growth H effects on the shape of the plant U unusual pigmentation 6 Y = budding of buds or flowers 72

Test A

(Xanthium spp.), Sorghum, corn, soybeans, rice, wheat germ, crabgrass, wheat and Cyperus rotundus tubers were introduced into a suitable growth medium and preemergence treated with a solution of the corresponding compound of formula I listed in Table XII in a non-phytotoxic solvent.

Another series of seeds and tubers of all the weeds and plants listed above were sown at the same time as the control. The control seeds were not treated, i.e. neither any compound nor any solvent was applied.

Other groups of all the aforementioned weeds of the crop plants were sprayed in the same developmental stages with the non-phytotoxic solvent alone and served as control plants. Both pre-emergence and post-treated plants and controls were grown in the greenhouse for six days, then all the treated plants were compared with the appropriate control plants and visually evaluated their chemical spraying responses. The results of Table XII show that the compounds of formula (I) are very effective herbicides.

I 261852

Table XII

<img img-format="tif" img-content="drawing" file="CS261852B2D00741.tif" id="idf0103" />

kg / ha 0,4 2,0 ​​0,4 0,4 ​​post-emergence beans 9C 9C 9C 9C cotton 9C 9C 9C 9C rack 10C 10C 1OC 10C rape 10C 90 9C 9C cassette 90 9C 9C 9C rope 90 90 9C 100 rudder 9C 90 5C 9G 50 8G Beetroot 10C 10C 9C 90 Oat 9C 9C 9C 90 Wheat 9C 9C 9C 90 Maize 9C 9C 10C 90 Soya 9C 60 9G 9C 90 Rice 10C 10C 5C 9G 80 Sorghum 9C 10C 9C 90 pre-emergence rack 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9H 9E 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H Sorghum 10E 10E 9H 9H 261852

Table XII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00751.tif" id="idf0104" />

kg / ha 0,4 0,4 ​​2 post-emergence beans 9C 9C 5C 10D cotton 9G 5U 5C 9G 5G 9G rack 10C 10C 5C 9G rape 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 10C 4C 7G 9C wheat 10C 3C 7G 10C maize 10C 10C 5U 9C soy 9G 9G 9G rice 10C 10C 9C 10C 9C 9C pre-emergence

9H 9G 9C 9G 9G 9G 9G 9G 9G 9G 9C 10E 9G 10E 9E 9G 9H 9H 9H 9H 9H 9H 9H 9H 9H 9G 9H 9G 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 261852

Table XII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00761.tif" id="idf0105" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00762.tif" id="idf0106" />

0 = 0

<img img-format="tif" img-content="drawing" file="CS261852B2D00763.tif" id="idf0107" />

kg / ha 2 0,4

post-emergence beans 6C 9G 3C, 8G, 8Y cotton 3C 9G 3C, 9G rack 5C 8G 3C, 9G rape 5C 9G 2C, 7G caste 3C 6G 2C rope 1C 8G 7G roaster 5C 8G 7G beetle 9C 9C oat 2G 6C wheat 5G 2C, 6G corn 1C 8G 1C, 8G soybean 2C 8G 3C rice 3C 8G 3C, 8G sorghum 2C 8G 2C, 8G preemergent rake 5C 9G 0 grape 9G - cassia 9G 0 shingle 10E 0 slice 2C 8G 3G shrimp 2C 9H 2G oat planted 8G 0 wheat 8G 4H corn 9G 3G soya 2C 8H 0 rice 10E 8H sorghum 9G 4G

Table XII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00771.tif" id="idf0108" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00772.tif" id="idf0109" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00773.tif" id="idf0110" />

at

kg / ha 0,4 0,4 ​​0,4 ​​post-emergence beans 9C 9C 9C 9C 9C 9C 9C rake 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 2C 6C 3C 7C 2C 10C 10C 10C 2C, 9G 2C, 6G 2C, 8G 2C, 5G wheat 3C, 6G 3C, 7G 1C corn 2U, 9G 10C 3C, 9G soybean 10C 5C, 9G 3C, 9G rice 3C, 8G 3C, 8G 6G sorghum 10C 9C 2H , 8G preemergent

9G 9C 9C 9G 9G 9G 9G 9G 9G 9C 5C 9G 10C 10C 10E 10C 2C 5G 2C 6G 4G 9H 10H 2C 9G 8G 9G 9H 9G 9H 5G corn 2U 9G 1OH 9G soy 9H 9H 9H rice 10E 10E 9H sorghum 9H 10H 9G 261852

Table XII - continue

<img img-format="tif" img-content="drawing" file="CS261852B2D00781.tif" id="idf0111" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00782.tif" id="idf0112" />

post-emergence

beans 9D 9G 9D 9G 9C 9C 9C 7C 9C 9C 9C 10C 10C 6C 9C 9C 10C cassia 5C 8G 5C 8G 10C 7G 8G 10C 2S 0C 8C 9C 5C 9H 6C , 9H 2C 8G 2C, 6G wheat 1C 5C, 8G 2C corn 9H 5C, 9H 10C soy 9C 3C, 9G 5C, 9G rice 4C, 8G 5C, 9G 5C, 8G sorghum 2C, 9G 3C, 9G 5C, 9G preemergent 9G 9G 9G 9G 9G 10C 9G 8G 9G 6C 9G 10C 10E 10E 10E 10E 10E 10E 10E 10E 10E 10E 10E 9E 9G 9C 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 8G 2G 8H 9H 9H rice 10E 10E 10E sorghum 9G 9H 2C, 9G 261852

<img img-format="tif" img-content="drawing" file="CS261852B2D00791.tif" id="idf0113" />

ir

<img img-format="tif" img-content="drawing" file="CS261852B2D00792.tif" id="idf0114" />

0 = 0

I o L9 *

<img img-format="tif" img-content="drawing" file="CS261852B2D00793.tif" id="idf0115" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00794.tif" id="idf0116" />

AND

<img img-format="tif" img-content="drawing" file="CS261852B2D00795.tif" id="idf0117" />

Oxygen

fO-C

<img img-format="tif" img-content="drawing" file="CS261852B2D00796.tif" id="idf0118" />

O

kg / ha 0,4 0,4 ​​0,4 ​​post-emergence beans 9C 5C, 8G, 6Y 6C, 6G, 6Y cotton 9C 2C, 2H, 7G 2C, 2H, 7G 10C 1C 2C, 8G 10C 3C, 9G 4G, 9G cask 9C 5G 5G 9C 2G 7G 2C, 5G 2G 2G, 2G, 8H 3C, 9H 3C, 9H 4G 1C 5G 1C 1C 1C 3C, 9G 2C, 9G 6G, 9G 1H 2H, 5G rice 1C, 7G 8G 2C, 9G sorghum 2U, 9G 9G 2U, 9G pre-emergence

9G 5G 8G 9G 9G 9G 9G cassia 6C 9G 5G 7G 9G 5G 7G 1C, 3G 0C 4C, 9G 2C, 8G 2C, 9G 8G 6C 2C, 8G 1C, 2G 2G 8G corn 3C, 9G 2C, 7G 2C, 8G 9G 3G 3G, 3G rice 9H 8G 9H sorghum 2C, 9G 8G 2H, 8G

Table XII - continuation 261852

<img img-format="tif" img-content="drawing" file="CS261852B2D00801.tif" id="idf0119" />

kg / ha ~ Z. x0 0,4 0,4 ​​0,4 ​​post-emergence beans 6C, 8G, 6Y 8C, 5G, 6Y 5S, 8G, 6Y cotton 2C, 2H, 8G 2C, 2H, 8G 3C, 3H, 9G rack 1C, 8G 3C, 7G 9C 2C, 9G 5C, 9G 9C cassia 5G 2C, 5G 1C shingle 3G 2G 1C, 5G 3g shark 3G 0 1C, 5G shrimp 1C 2H 5C, 9H 0 0 2C, 5G wheat 0 0 1C corn 6H 7H 7H 7G soybean 6H 2H, 9G rice 2G 6G C sorghum 7H 2C, 9G 8H preemergent rack 4G 0 8G rape 5C, 9G 5C, 9G 8G cassia 2C, 5G 3C, 7G 3G shingle 0 2G 5G rudder 0 2G 0 rake 0 0 9H oat plan 0 0 5G wheat 0 0 3G corn 2G 4G 1C, 7G soybean 1C 0 2C, 4H rice 0 0 9H sorghum 2H 3G 8G 261852

Table X11 - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00811.tif" id="idf0120" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00812.tif" id="idf0121" />

o4

I a: s S t i i i O = Í i

I tni

X

WITH

OqZ&gt; I: 2

kg / h aP ux cx 0 0.4 aP 0 0.4 a: CO □: 0.4 post-emergence bean 6C, 8G, 6Y 9C 9C, 9G cotton 2H, 3C, 8G 9C 9C, 9G 6C 3C, 9G 10C 10C cassia 3C, 9G 10C 10C cassia 5C 9C 9C 9C clover 2G 10C 6C, 9G cobbler 0 2C, 6G 3G beetle 3C, 8H 3C, 9H 6C, 9H 9G 3C, 9G wheat 0 1C , 2G 3C, 5G corn 6H 6H 9H soybeans 2H, 8G 5C, 9G 4C, 9G rice 2G 5C, 9G 9C sorghum 3G 3C, 9G 4C, 9G pre-emergence rack 9G 9G 9G rape 9C 9G 9H cassia 2C 2C, 9G 3C, 9G shackle 0 10E 10E rudder 0 5G 2C, 5G beetle 9H 9H 9H 9G 9G 9G wheat 2G 3G 8H corn 1C, 7G 9H 2U, 9G soybean 2C 9H 9H rice 5G 10E 10E sorghum 8G 9H 9H 281852

Table XII - Editing i 'o x' u

OS o (λ 1 x 2ο = ω ar

<img img-format="tif" img-content="drawing" file="CS261852B2D00821.tif" id="idf0122" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00822.tif" id="idf0123" />

2 2 O = ψ 5 .Lf 2 20 ^ 2

kg / ha OO 1 O 0,4 2 U 0,4 □ T ≥ A • Q 0,4 post-emergence bean 9C, 9G 5H, 8C 5C, 9H cotton 7C, 9G 9C 10C rack 10C 10C 9C rape 10C 10C 10C cassia 6C, 9G 9C 9C shingle 10C 9C 9C 9C shake 1C 6C 3U, 5G shovel 3G 9C 10C oat wild 0 6C 3C, 7G wheat 0 3G, 4G 3C, 8G corn 9H 5U, 8G 9C soybean 5C, 9G 6H, 8G 5G, 9G Rice 2C, 9G 7C 8C Sorghum 8H 9C 10C Pre-emergence rack 9G 9G 9H 9G 5H, 9G 8H, 9G 5C, 9G 5H, 8G 8H, 9G Cashew 10E 10E 10E 1S 8G 8G 8G 8H 5H, 9G 5H, 9G 8G 7G 8G 9G 8H 7G 8G 9G 8H 9G 8H 9G 8H 9G 8H 9G 8H 8G

Table X11 - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00831.tif" id="idf0124" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00832.tif" id="idf0125" />

o nf1 o

7T and □ f1

<img img-format="tif" img-content="drawing" file="CS261852B2D00833.tif" id="idf0126" />

2 o-ô 2 ^ - i - 1 x Sn

u X u

kg / ha 0,4 2 0,4 post-emergence beans 8H, 9G 3C, 9G, 9D 3C, 9G, 9D 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C ZC, 6G 6G 4C, 7G 2C, 6G beetroot 8C 10C 9C oat 9C ZC, 5G wheat ZC 9C 1C, 4G corn 5H, 7G 9C 2U, 8H 5H, 8G 6C, 9G 6C, 9G rice 8C 9C 6C, 8G 2H, 7G 9C 3C, 8G preemergent

9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 7G 7G 7G 8G 9H 9G 9H 9H 9G 8G 7G 9G 9G 9G 9G 9G ZC, 9G soy 7H, 8G 9H 7H rice 7E, 8G IOE IOE sorghum 7H, 9G 9H 9H 261852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00841.tif" id="idf0127" />

kg / ha 2 0.4 2 post-emergence beans 3C, 9G, 10D 3C, 9G, 9D 9G, 10D cotton 5C, 9G 5C, 9G 9C rack 10C 9C 10C beet 10C 9C 9C cassette 9C 3C, 7G 9C rope 9C 2C, 7G 9C 9C 5C, 8G 9C 8C 9C 9C 9C 9C 9C 5C, 8G 9C 9C 8C 5C, 8G 9C 9C 8C 5C, 8G 9C 9C 8C 5C, 8G 10C preemergent

5G, 9G 9G 9G 9C 9G 9G 9G 9C 9C 9G 9G 9C 9G 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H rice 10E 10E 10E sorghum 9H 9H 10H 261852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00851.tif" id="idf0128" />

XXi A 'b.

<img img-format="tif" img-content="drawing" file="CS261852B2D00852.tif" id="idf0129" />

4G, 9G 5H, 8G, 6F 1C cotton 9C 4C, 7G 10C 4G 0 grape 9C 8C 0 cassette 9C 3C, 8G 0 shade 9C 8C 0 4C, 7G 5G 0 1 0C 8C 1C 8C 1H 9C 4C 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 10E 7G 1C 9G 5H 8G 1C 9G 5H 8G 1C 9E 5H 8G 1C 10E 10E 0C 9C 5H 8G 0 9H 5H 8G 0 9H 3G soy 9H 5H, 8G 1C rice 10E 8H, 9G 0 sorghum 9H 5H, 8G 0

TableXII - · continued

I 2 81 8 5 2

<img img-format="tif" img-content="drawing" file="CS261852B2D00861.tif" id="idf0130" />

F? N-C (O) NH-C-NH-

COOH CH * CH, kg / ha. "10 Z 2 0,4 post-emergence beans 2C, 2H 1C 0 0 cotton 0 0 raft 0 0 0 0 rape 0 iO 0 0 cassia 0 1C 0 0 rope 0 0 0 0 rush 0 0 0 2G beetle 2G 0 0 1C, 2H oat plantain 0 0 0 0 wheat 0 0 0 0 maize 0 0 0 0 soybean 1C 0 0 0 rice 5G 0 0 0 sorghum 3G 0 0 preemergence raffle 7G 1C 0 0 rape 9G 0 0 0 kasie 1C, 5G 1G 0 0 ryegrass 9G 9G 0 0 rudder 1C 0 0 0 1C, 0G 0 0 0 0C 0 0 0 0C 0C 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 sorghum 5C 0 0 0 0 261852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00871.tif" id="idf0131" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00872.tif" id="idf0132" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00873.tif" id="idf0133" />

post-emergence

beans 8C 9C 9C BAV-workers over 6C, 9G 5C, 9G 5C, 9G morningglory 10C 9C 5C, 9G cocklebur 9C 5C, 9G 6G cassia 5C, 7G 5C, 9G 9C nutsedge 7G 3C, 8G 4G rdsička 1C 2C, 8G 3G barnyardgrass 1C , 7G 9C 2G 1C 7C 0C wheat 1C 7C 2G corn 3U, 8G 5U, 9C 8G soy 9C 9C 9C rice 3C, 7G 5C, 8G 2C, 5G sorghum 8G 9C 1C, 9G pre-emergence rack 9G 9G 8G 9G 9G 9G 9G cassia 8G 9G 9G 9G 9G 10E 2G 6G 4C 9G 9G 9G 9G 9G 5G 9H 9H 5G 9G 9H 5G 9G 9H 10C 2G 7G 9G 9H 2C 4G 9H 10E 2G 5G sorghum 1C, 9G 10E 8G

I 261852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00881.tif" id="idf0134" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00882.tif" id="idf0135" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00883.tif" id="idf0136" />

kg / ha 0,4 0,4 ​​0,4 ​​post-emergence beans 9C 10D 9C cotton 9C 3C, 9G 5C, 9G rack 10C 10C 9C rape 9C 5C, 9G 3H, 9G cassette 9C 3C, 8G 9C rope 2C, 6G 2C, 9G 6C, 9G 3C, 8G 5C, 8G 9C raspberries 10C 9C 5C, 8H 9C 5C, 8G 9C 5C, 7G 9C 8C 5C, 9G 8C 5C, 9G 9C sorghum 5C, 9G 3U, 9G 2C, 9G pre-emergence 9G 9G 9G 9G 9G 9G 9G 10E cassia 9C 9G 9G 10C 9G 9G 10C 9C 5C, 9H 2C, 8G 2C, 8G 2C, 8H 2G wheat 1C, 9H 9G 0 maize 2C, 9H 9G - soy 9H 8H 9H rice 10E 10E 9H sorghum 2C, 9H 9H 9G 261852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00891.tif" id="idf0137" />

kg / ha 0,4 0,4 ​​0,4 ​​post-emergence beans 9C 4C, 9G, 6Y 3C, 5G, 6Y cotton 5C, 9G 2C, 3H 1C rack 10C 5C, 8G 0 rope 10C 3C, 8G 5C cassia 9C 2C 0 rope 6C, 9G 6G 0 2C, 6G 2G 2C 2C 2C, 6C 2C 2C 2C 2C, 6C oat 9C 0C 1C wheat 9C 0 2G corn 9C 2G 1C, 7G soybean 9C 5C, 7G 1C, 5G rice 9C 2C 2C, 4G sorghum 9C 5G 2C , 7G preemergent

repository 9G 8G 3G splice 9G 8G - cassette 9G 0 0 spade 10E 10E 1OE spade 9H. 2G 2G beetroot 9H 9G 1G, 8H oat 3C, 9G 4G 0 wheat 9H 5G 0 maize 10E 2C, 7G 1C soybean 9H 1C, 5H 0 rice 10E 9H 8H sorghum 10H 2C, 9G 8G 261852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00901.tif" id="idf0138" />

kg / ha 0,4 0,4

post-emergence beans 9C 9C cotton 9C 9C rack 10C 10C rape 9C 10C rack 9C 9C rass 2C, 8G 7G rabbit 2C, 8G 9C rake 5C, 9H 6C, 9H 1C, 8G 2C, 7G wheat 1C, 7G 2C, 6G maize 10C 9C soybeans 2C, 8G 9C rice 3C, 8G 5C, 8G sorghum 2C, 8G 2C, 8G preemergent rake 9G 9G 9G 9G 9G 9G 9G 9G 9G 8G 9G 2C, 9G 1C, 8G 9H 2C, 7G 1C, 8G wheat 1C, 5G 7G corn 1C, 9G 2C, 9G soya 9H 9H rice 10E 10E sorghum 2C, 9G 9H 261852

TableXII - continued

OO

<img img-format="tif" img-content="drawing" file="CS261852B2D00911.tif" id="idf0139" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00912.tif" id="idf0140" />

kg / ha 0,4 0,4

postemergence bean 9C 9C Cotton 9C 5C, 9G morningglory 10C 10C cocklebur 9C 9C cassia 9C 10C flatsedge 4G 7G crabgrass 1C, 5G 9C barnyard grass 6C, 9H 9C oats false 4G 3C, 7G Wheat 2G 3C, 6G Corn 9C 9C soy 5C, 9G - rice 5C, 9G - sorghum 1C, 8G 5C, 9G preemergence morningglory 3C, 9G 9G cocklebur 9G 9G cassia 8G 10E flatsedge 7G 10E crabgrass 5G 2C, 9G barnyard grass 9H 9H oats false 7G 9H wheat 5G 9H corn 1U, 9G 9H soy 9H 9H rice 9H 10E Sorghum 1C, 9G 9H 281852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00921.tif" id="idf0141" />

kg / ha '0,4 0,4

post-emergence beans 9C 9C cotton 6C, 9G 4C, 9G rack 10C 10C rape 10C 9C rack 9C 5C, 9G rake 1C, 8G 2C, 8G rabbit 3C 2C, 6G rabbit 9C 3C, 9H raspberries 1C, 2G 3G wheat 1C, 4G 2G corn 9C 3U, 8G soybeans 9C 5C, 9G rice - 3C, 7G sorghum 5C, 9G 2C, 8G preemergent rake 9G 9G rape 8G 9G cassia 8G 8G rush 5G 2C, 9G 2C 9C 2C, 8G 9H 2C, 9H oat 5G 2C, 8G wheat 3G 4G corn 8G 9G soy 9H 9H rice 9H 9H sorghum 2C, 9G 9H 261852

Table XII - continued &lt;*&gt;

X

<img img-format="tif" img-content="drawing" file="CS261852B2D00931.tif" id="idf0142" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00932.tif" id="idf0143" />

kg / ha 0,4 0,4 ​​post-emergence beans o 5C, 8G, 6Y 9C cotton 5C, 9G 9C rack 9C 9C rape 5C, 9G 10C cassia 5C, 9G 5C, 9G rudder 0 8G rudder 5C, 8G 4G beetle 3C, 7H 9C grain oat 2C 1C, 2G wheat 0 1C, 2G maize 8U, 9G 5U, 9H soybean 5C, 8G 9C rice 3C, 8G 3C, 8G sorghum 2C, 9G 8G pre-emergence rack 9G 9C rape 8G 9G cassia 8G 3C, 8G rope 9G 10E 2C, 8H 2C, 8G beetle 2C, 9H 5C, 9H 4G 1C, 9G wheat 0 9H corn 2C, 8G 9G soybean 7H 9H rice 9H 10E sorghum 1C, 9G 5C, 9H 261852

TableXII - continued

rC

AND

O

O

<img img-format="tif" img-content="drawing" file="CS261852B2D00941.tif" id="idf0144" />

0.4 w-1

<img img-format="tif" img-content="drawing" file="CS261852B2D00942.tif" id="idf0145" />

kg / ha 0,4

post-emergence beans 9C 8C, 9G cotton 2C, 2H, 5G 4C, 9G 9C 10C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 9C 4G, 8G 9C wheat 2C, 8G 9C, 8G corn 2C, 9H 5U, 9C soybean 2C, 8G 9C rice 3C, 8G 5C, 9G sorghum 2U, 9G 9C pre-emergence rack 9G 9G 9G 8G cassia 9G 9G rake 1C, 9G 9H 9C 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H 9H

TableXII - continued kg / ha

<img img-format="tif" img-content="drawing" file="CS261852B2D00951.tif" id="idf0146" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00952.tif" id="idf0147" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00953.tif" id="idf0148" />

0.4

<img img-format="tif" img-content="drawing" file="CS261852B2D00954.tif" id="idf0149" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00955.tif" id="idf0150" />

0.4 post-emergence

beans 9C 10D, 9G 9G cotton 9C 6C, 9G 10C rack 10C 10C 10C rape 9C 5C, 9G 9C cassia 6C, 9G 9C 9C rake 6C, 9G 7G, 9G 10C 4C, 8G 5C, 8G 9C rake 9C 10C 9C oyster 9C 9C 9C wheat 9C 9C 9C maize 10C 9C 10C soy 9C 9C 9C rice 6C, 8G 9C 5C, 9G sorghum 9C 9C 10C pre-emergence

9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9C 9C 1C 9G 9C 9C 9C 1C 9H 9C 9C 1C 9H 10E Soybean 9H 9H 9H Rice IOE IOE Sorghum 5C, 9H 9H IOE

I 2B1852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00961.tif" id="idf0151" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00962.tif" id="idf0152" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00963.tif" id="idf0153" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00964.tif" id="idf0154" />

kg / ha 0,4 0,4 ​​0,4 ​​post-emergence beans 8C, 9G 9C 9C cotton 6C, 9G 6C, 9G 2C, 3H, 8G rack 9C 9C 2C, 8G beet 2H, 8G 5C, 9G 2C cassette 5C, 9G 9C 1C, 6H 9C 8C 9G 9C 9C 9C 9C 8C 9C 9C 9C 8C 9C 8C 9C 9C 8C 9C 8C 9C 9C 8C 9C 8C 9C 9C 9C 8C Rice 5C, 9G 9C 8G sorghum 3C, 9H 9C 9G pre-emergence rack 9G 10E 9G rape 8G 10E 10E cassette 8G 3C, 9G 2C, 8G rope 10E 10E 10E rudder 2C, 5H 5C, 9G 2C, 8G beetle 9H 5C, 9H 3C, 9H Grass Oat 6G 5C, 9H 1C, 5G Wheat 6G 10E 2C, 9H Maize 8G 10H 9G Soya 2C, 5H 9H 9H Rice 9H 10E 10E Sorghum 1C, 9G 10H 9H 261852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00971.tif" id="idf0155" />

cA £

Q

O 4 a; ~ y

O ~ Q A ".

JJ

-T ', t, * G. j i &lt;u

<img img-format="tif" img-content="drawing" file="CS261852B2D00972.tif" id="idf0156" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00973.tif" id="idf0157" />

0.4 t &amp; lt; &amp; quot; &amp; gt ;.

O ~ S £

<img img-format="tif" img-content="drawing" file="CS261852B2D00974.tif" id="idf0158" />

post-emergence

beans 9C 4C, 7G, 6G 9C cotton 2C, 3H, 9G 2C 9C rack 5C, 9G 2C 10C rape 3C, 8G 2C, 5G 9C cassia 9C 1C 9C rope 9C 1C, 5G 8G 9C 3C 9C 9C 3C 10C Fresh oats 6C, 9G 0 9C Wheat 5C, 8G 0 9C Corn 9C 1C, 7H 9C Soya 8C 2C 9C Rice 8C 2C, 7G 10C Sorghum 9C 1C, 5G 10C pre-emergence

rack 10E 0 9G rape 9G 0 9G raccoon 8G 0 8G maize 10E 10E 10E rosette 5C, 9G 0 2C, 9G raspberries 7C, 9H 2G 2C, 9H oat flour 4G, 6G 0 2G, 7G wheat 9H 0 9H corn 9H 1C, 4G 9G soy 9H 0 9H rice 10E 8H 10E sorghum 9H 3G 9H 281852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00981.tif" id="idf0159" />

<img img-format="tif" img-content="drawing" file="CS261852B2D00982.tif" id="idf0160" />

kg / ha 0,4 0,4 ​​0,4 ​​post-emergence beans 9C 9C 9C cotton 9C 9C 9C rack 10C 10C 10C rape 10C 2C, 8G 9C cassette 10C 3C, 8G 9C rope 5C, 9G 1C, 8G 2C, 9G 3G 9C 1C, 8G 6C, 9H 5C, 8H 9C 3C, 7G 1C, 5G 4C, 7G wheat 2C, 6G 1C 4C, 6G corn 10C 90 9C soybean 6C, 9G 9C 8C rice 5C, 9G 5C, 9G sorghum 2C , 9G 3C, 9G 3C, 9G pre-emergence 9G 9G 9G 9G 9G 9G 9G 8G 9G 2C, 8G 9G 10E 1C, 9G 10C 2G 1C, 9G 2C, 9G 2C, 9H 2C, 9H 4C, 9H 1C , 7G 2C, 8G 2C, 7G wheat 6G 6G 9H corn 2U, 9G 10H 9G soybean 9H 9H 9H rice 10E 10E 10E sorghum 2C, 9G 9H 9H, 261852

TableXII - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D00991.tif" id="idf0161" />

kg / ha 0,4 0,4 ​​0,4 ​​post-emergence beans 9C 9C 6C, 9G cotton 9C 9C 9C rack 10C 9C 10C rape 9C 9C 9C cassette 9C 9C 10C rope 10C 2C, 8G 9C rudder 5C, 8G 2C, 7G 9C Rabbit 9C 9C 10C 9C 3C, 7H 8C 5C, 8G 1C, 5H 8C maize 7U, 9C 9C 9C soybean 6C, 9G 9C 5C, 9G 9C 5C, 8G 6C, 9G sorghum 9C 9C 9C pre-emergence

rack 9H 9G 9G 9G 9G 9G 9G 9G 9G 9G 9G 9C 9G 9C 9G 9C 9C 9C 2C 8G 10C 9C 9C 2C 9G 1C , 6G 9H corn 9G 1U, 9G 9H soy 9H 9H 9H rice 10E 10E 10E sorghum 9H 9H 5C, 9H 261852 73 74

Test B

Two large bowls of pear-shaped form were filled with fertilized and polished Fel-lsington clay-sandy soil. The monks were sown with seeds of corn, sorghum, Kentucky grassland, and several weeds. Another variety of soybean, Cype-rus rotundusj and seeds of many other broad-leaved weeds were used to test the following weeds: Digitaria sanguinalis, Echinochloa crusgalli, Avena fatua, Sorghum halepense, Setaria faberii), Paspalum dilatatum, Bromus secalinus, Mustard (Brassica arvensis, Xanthium pennsylvanicum), Amaranthus retroflexus, Ipomoea hederacea ), cassia (Cassia torus), sida (Sida spinosa),

Another smaller bowl was also filled with the ground and sowed seeds of rice and wheat. Another small bowl was planted with sugar beet. The seed culture plates of the plants were pre-treated with solutions of the compounds of general formula I in a non-phytotoxic solvent (i.e., the solutions of the compounds were sprayed onto the surface of the soil prior to seed germination). Also using the seeds of the same plants were prepared duplicates of the above described four- which have not been treated with sprays which have been used as controls.

Twenty-eight days after the treatment, the plants were compared and their treatment responses evaluated in the test and control dishes; the data found are shown in Table XIII. 2 818 5 2

Table XIII

Pre-emergence efficiency (Fallsington clay-sand soil) 0 ll

<img img-format="tif" img-content="drawing" file="CS261852B2D01011.tif" id="idf0162" />

COCH "

kg / ha 1/128 1/64 1/32 9S 9C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 1C 10C 1C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10E bark 10C 10C 10C sugar beet 8G 5H 10C 10C 10C maize 10C 1OC 10C mustard 10C 1OC 10C rapeseed 7G 5C 7G 8G spoon 10E 10E 10E cotton 7G 8G 8G 5 rack 7G 7G 8G 6G 8G 8C 10C 10C sida - - potato 10C 10C 10C durman 9G 9C 9G 9C 9G 9 soybean 8G 8G 5C 10C rice 10C 1OC 1OE wheat 10C 1OC 1OC 261852

Table XIII - continued

Pre-emergence efficiency (Fallsington clay-sandy soil)

O

SO 2 NH-C-NH-

COCI-L dose kg / ha broom rabbit sorghum sorghum oats marshmallow halebskýpaspalumbér lipnice bark beet sugar maize mustard beetle beetle safflower cotton beetle kasie sida potato durman soybean rice wheat 1/16 li / 4

10C 10C 10C 10C 10C 10E 7C 5C 8C 8C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 8C 8G 8G 8G 8G 8G 8G 8C 8G 8C 10E 1OE 9G 9H 1OH 261852

Table XIII - continued

Pre-emergence efficiency (Fallsington clay-sandy soil)

<img img-format="tif" img-content="drawing" file="CS261852B2D01031.tif" id="idf0163" />

SO2 NH-N-NH-CH2CH3CH3

dose kg / ha 1/64 1/32 1/16 mite 8G 30 9G 9C 10C shrimp 10C 10C 10C sorghum 10C 10C 1OC oat fried 8G 80 10C 9G 9C sorghum sorrel 10C 10C 10C paspalum 10C 10C 10C 10C 10C 10C 10C 10C 10C lip 10C 10E 10E brome 10C 10C 10C sugar beet 10C 10C 10C maize 10C 10C 10C mustard 10C 10C 10C 8G 8G 8C 7C 8C 7C. shade 10E 10E 10E cotton 9G 9C 10G 9G 9C rack 8G 8C 10C 10C cassia 10C 1OC 1OC 10C 10C 10C 10C 100C durman 9G 9C 10C 10C soybean 10C 9G 9C 8G 50 rice 10E 1OE 10E wheat 8G 8C 1OC 10C 261852

Table XIII - continued

Pre-emergence efficiency (Fallsington clay-sandy soil)

<img img-format="tif" img-content="drawing" file="CS261852B2D01041.tif" id="idf0164" />

Dose kg / ha Rattle Shrimp Sorghum Oat Flycatcher Halebpaspalbum Lipnice Brome Beet Sugar Corn Mustard Skewer Ladybird Shepherd Cotton Capercaillie Cassia Sida Cloud Durman Soybean Rice Wheat 1/64 1/32 1/16

8G 3C 9G 9C 10C 10C 10C 10C 10C 10C 10C 8C 8C 10C 9C 9C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 9G 9C 10C 9G 9C 8G 8C 10C 10C 10C 10C 10C 10C 10C 10C 9C 9C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 8C 8C

Table XIII - continued

Preemergence Efficacy (Fallsington's Aluminum-sandy Soil) D-OCH2-NH-C (NH)

dose kg / l 1 (/ 64 ...... 1/32 ..... -------------! / 46 clove 7G 3C 9G 9C 10C henge 9G 9C 10C 10C sorghum 10C 10C 10C 10c 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 8G 9C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 9C 8C 9C 9C 10C 8G 5C 8G 8C rice 8G 8C 10C 10C wheat 3G 4G 5G

Table XIII - continued

Preemergence efficiency (Fallsington clay-sandy soil)

<img img-format="tif" img-content="drawing" file="CS261852B2D01061.tif" id="idf0165" />

dose kg / ha 1/64 1/32 1/16 mite 7G 8G 5C 10C shrimp 3G 7G 7C 9G 9C sorghum 7G 9G 8C 10C oat plantain 0 10C 5G 3C sorghum haleb 6G 7G 7C 8G 8C paspalum 0 0 3G beer 6G 3C 5G 3C 8G 8C 7G 3C 8G 5C 10C bark 3G 3G 6G 3C sugar beet 10C 10C 10C maize 6G 5H 7G 5C 10C mustard 10C 10C 10C beet 8G 3C 10C 8G 5C 7C 7G 3C 8G cotton 10C 8G 9G 5C rack 8G 8C 10C 10C cassia 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C

Table XIII - continued

Preemergence efficiency (Fallsington clay-sandy soil) 0

<img img-format="tif" img-content="drawing" file="CS261852B2D01071.tif" id="idf0166" />

1/16 1/4 batch kg / ha rush raspberry sorghum oats hare cuttlefish halebspaspalbum leek bacon beet sugar corn mustard chopped beetle saffron caviar reputation cassia sida cloud durman soybean rice wheat

0 5G 10C 10C 10C 10C 0 5G 10C 10C 5G 8G 3C, 3G 6G 8G 10E 10E 10E 7G 10C 4G 8G, 8C 10E 10E 7G 8G 10E 10E 6G 10E 4G 7G 4G 10E 5G 7G, 2C 0 8G, 5C 5G 7G 2G 6G 7G, 7H 8G, 8H 10E 10E 2G 8G, 5C 261852

Table XIII - continued

Pre-emergence efficiency (Fallsington clay-sandy soil)

<img img-format="tif" img-content="drawing" file="CS261852B2D01081.tif" id="idf0167" />

dose kg / ha 1/32 1/16 3 ^ 4 worms 0 4G 7G shrimp 10C 10C 1OC sorghum 10C 10C 1OC oat 8G, 7C 8G, 8C 10C sorghum sorrel 9G, 9C 10G 1OC paspalum 0 0 6G beer 4G, 3H SG 5H 9G 9G bluegrass 10E 10E 10E brome 8G 9C 10E 10E sugar beet 10C 10C 10C corn 8G, 8C 1OG 10C mustard 10C 10C 10C cocklebur 7G, 2C 7G, 5H 7G, 5H Iaskavec 10E 10E 10E flatsedge 10E 1OE 1OE cotton 7G 8G 8G morningglory 5G 7G 8G cassia 7G 8G, 3C 8G, 8C sida 7G 7G 1 OC velvetleaf 8G, 7C 1 OC 1 OC datura 7G 7G 8G, 5C soy 8G, 3H 7G, 5H 9G, 9C rice 10E 1OE 1OE wheat 4G, 2C 6G, 4C 7G, 4C 261852

Table XIII - continued

Pre-emergence efficiency (Fallsington clay-sandy soil) dose kg / ha

<img img-format="tif" img-content="drawing" file="CS261852B2D01091.tif" id="idf0168" />

rosičkaježatkači year oats pJanýčirok halebskýpaspaluin foxtail brome LIPNICE sugarbeet corn cocklebur mustard loving sedges cotton morning glory cassia sida velvetleaf datura soybeans wheat rice 0 0 0 0 0 0 0 0 0 6G 3H000ooooooooooo oooooooo about

10C ooooooooooooooooooooo o

6G

7G, 5HO

5G 0

5G

5G

O

Ooooo

6G, 5CO

I 261852

Table XIII - continued

Preemergence Effectiveness (Fallsington's sandy loam soil) C (H) NH 4 - NH - C - NH - SO 2 -

CN / CH,

dose 1/32 1/16 1/4 1 0 0 4G 7G, 3C 8G, 3C 10C Sorghum 6G, 3H 5G 10C Oranges 0 0 6G, 3C Hobbies 0 0 5G, 5H paspalum 4G 5G 10E Berries 3H 3H 10H lipnlce 9G 10E 10E borage 0 2G 8G, 8C sugar beet 4G 4G 7G, 7C maize 0 4G 5G, 5H mustard 9G 9G, 5C 10C beet 3H 2H 5G, 5H 10E 10E 10E 10C 5G 5G 8G • cotton 0 0 3G, 3G rack 3G 6G 4G cassia 0 0 3G sida - - 5G, 5H 7G, 7C 10C 10C durman 0 2G 4G soybean 0 0 6G, 6H rice 9G, 9C 7G, 5C 10E wheat 3G 4G 6G 261852

Table XIII - continued

Pre-emergence efficiency (Fallsington clay-sandy soil) Π-, o

II

CO-CH (CH 2)

-NH-C-NH-SO (O) - C-N (CHO)

dose kg / ha 1/32 1/16 1/4 0 0 crabgrass, barnyardgrass 6G 10C 10C 10C cir mesh 9G, 9C 10C 1 OC wild oat 2G 6G 7G, 5C sorghum halebský 8G, 8C 10C 1 OC Paspalum 0 0 5G, 3H 3H foxtail 4G, 3H 10C 10C 10C 10C bark 10G 10C 10C 10C 10C 10C 10C corn 6G, 3H 7G, 7H 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 6G 7G 9G 8G 8G 8G 1G 8G 8G 8G 5G 1G 8G 5G 10G 10C 10C 10C 10C 10C 8C 8G 5C 7G 5H 7G 5H 8G 8G 10G 10G wheat 2G 4G 6G

<img img-format="tif" img-content="drawing" file="CS261852B2D01121.tif" id="idf0169" />

261852

Table XIII - continued

Pre-emergence efficiency (Fallsingtoin clay-sandy soil)

<img img-format="tif" img-content="drawing" file="CS261852B2D01122.tif" id="idf0170" />

dose kg / ha l | / 32 1/16 1/4 bunch 0 2G 7G shrimp 10C 10C 10E sorghum 10C 10E 10E oat 4G 7G, 3C 10C sorbic harsh 10C 10C 1OC paspalum 5G 7G 10C beer 6G, 3H 9G, 9C 10C 10C 10E 10E borage 10E 10E 10E 10E 10E 10E 10E 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 8C 8C 9G 9G 1C cassette 8G, 8C 8G, 5C 8G, 9C sida 10C 10C 10C 10C 10C 10C 10C durman 8G, 5C 8G, 7C 8G, 8C 8G, 5H 9G, 5H 9G, 5H 8G, 9C 1OC 1OE wheat 6G 6G , 5C 10C 261852

Table XIII - continued

Pre-emergence efficiency (Fallsingtom sand-clay soil) -O-CH (CH3) 2

NH ~ S

<img img-format="tif" img-content="drawing" file="CS261852B2D01131.tif" id="idf0171" />

CHti '.3

dose kg / kg 1/32 1/16 1/4 teaspoon 0 ..... 4G 8G beetroot 0 6G, 3H 8G, 5H sorghum 6G, 3H 7G, 3H 1OC oat grapes 0 0 5G, 3C sorghum hamburger 2H 2H 6G , 5H paspalum 0 0 4G beer 0 0 7G leeks 5G, 6C 7G, 8C 1OE bacon 0 6G, 3C 7G, 8C sugar beet 10C 10C 10C maize 7G, 7H 10C 10C mustard 10C 10C 10C beet 8G, 8H 8G, 8H 8G, 8H 10E 10E 10E 10E 10E 10E 10E 10E 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 5G, 3C 5G, 3C 7G, 4C wheat 0 0 2G

Table XIII, continuation 281832

Preemergence efficiency (Fallsingtotn alluvial soil)

<img img-format="tif" img-content="drawing" file="CS261852B2D01141.tif" id="idf0172" />

dose kg / ha 1/16 1/4

crabgrass 3H 6G barnyardgrass 6G 4C 10C Sorghum 10C 10C oats false 6G 8G 5C sorghum halebský 6G, 3H 8G, 8C Paspalum 0 4G foxtail 3H 6G, 2C bluegrass 8G 10E brome 10E 10E sugarbeet 8G, 8C 10C Corn 5G, 5H 9G , 9C mustard 10C 10C cocklebur 8G, 5H 8G, 3H amaranth 10C 10C flatsedge 10E 10E cotton 5G 5G morningglory 6G 8G, 8C cassia 4G 8G, 8C Sida 6G 5C 10C velvetleaf 8G, 8C 10C datura 5G, 3H 10C soy 8G, 8C 8G, 8C rice 10E 10E wheat 0 3G 261852

Table XI11 - continued

Pre-emergence efficiency (Fallsington clay-sandy soil) dose kg / ha mackerel shrimp sorghum oats marshmallow halebspaspalbum leeks brome beet sugar corn mustard beetroot liqueur safflower cotton beetle cassia sida potato durman soybean rice wheat CH3 ° \ q -NH-C-NH- 302 \ oysters 1/16 1/4

6G, 3H

10C

6G, 6G, 3H0

2H)

9G

10E7G, 8C6G, 5H

10C6G, 2C10C10E

3G

4G

3G

10C

8G

8G, 8C7G, 5H8G, 8C

10C

10C

10C

10G

5G

5G, 2C

10E10E10C9G, 9C10C8G, 3C10C10E8G10C6G10C10C10C9G, 9C10E5G, 2C

J 261852

Table XIII - continued

Pre-emergence efficiency (Fallsington clay-sandy soil) CH, Ck CH3 o

-NH-N-NH-S-COO

<img img-format="tif" img-content="drawing" file="CS261852B2D01161.tif" id="idf0173" />

<img img-format="tif" img-content="drawing" file="CS261852B2D01162.tif" id="idf0174" />

kg dose 1/16 1/4 scoop 6G 7G beetroot 8G, 4C 8G, 6H sorghum 9G, 8C 10C oat 6G, 2C 8G, 5C 8G horseradish, 2C 10C paspalum 3G 5G 6G 8G, 4C leek 9G 10E bacon 7G 10C sugar beet 10C 10C maize 9G, 9C 10C mustard 10C 10C 8G, 8C 8G 8C 8C 8C 8G, 8C 10E 10E 7G 9G 9G, 5H 9G, 5H 9G, 9C 9G, 9C cassette 8G, 9C 10C sida 10C 10C potato 10C 10C durman 5G 8G, 7C soy 9G, 9C 9G, 9C rice 6G, 3C 8G, 8C wheat 0 0 261852

Table XIII - continued

Preemergence Efficacy (Fallsington's sandy loam soil) of N-Cl 2 -CH 2 CH 2 -O-CCH, 0 per kg / ha 3 1/16 1/4

0C 10C 10C 10C 10C sorrel 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 8C , 7H mustard 10C 10C sprout 7G, 5H 8G, 5C spice 10E 10E spade 10E 10E cotton 3g 8G spoon 5G 10C cassette 7G, 5C 8G, 7C sida 3H 7G, 5H potato 10C 1OC durman 5G 7G soybean 8G, 8H 9G, 9H rice 10G 1OE wheat 5G 6G 281852

Table XIII - continued

Preemergence Effectiveness of the Fallichester Aluminum Sand)

<img img-format="tif" img-content="drawing" file="CS261852B2D01181.tif" id="idf0175" />

1/16 1/4 batch kg / ha bumblebee sorghum sorghum oats marshmallow h &amp; amp; skalpaspalumber llpnice brome beet sugar maize mustard beetle beetle safflower cotton cavalier kasie sida cloud &amp; durman soy rice wheat

0 4G 10C 10C 10C 10C 8G, 2C 8G, 6C 9G, 9C 10C 5G 8G, 9C 6G, 4H 10C 10E 10E 10E 10E 9G, 9C 9G, 9C 10C 10C 8G, 5H 7G, 5H 10E 10E 10E 10E 6G, 2H 8G, 5H 10C 8G, 5C 7G, 3C 8G, 7C 9G, 9C 10C 10C 10C 6G 8G, 7C 8G, 8H 8G, 9H 10E 10E 7G 10C; . z Z 6 183 2

Table XIII - continued

Pre-emergence efficiency i (Fallsington clay-sandy soil) ch3o.

XC "NO ch30

Cl-CHzCHzO-C, kg / ha 1/16 1/4 bunch 0 0 raspberries 4G 4G sorghum 5G 7G oat fowl 3G 0 sorghum sorbet 0 6G, 6E paspalum 0 0 beer 0 3H leeks 6G 8G brome 0 3G sugar beet 10C 10C corn 4G, 2H 7G, 5H mustard 9G 10C sprout 8G, 5H 8G, 5C spoon 10E 10E spade 8G 8G cotton 7G, 5H 8G, 5H rack 8G 8G, 5C cassette 7G, 3C 8G, 9C sida 5G, 6H 10C 7G, 7C 10C durman 3G 5G soy 3G 6G, 5H rice 6G, 3C 5G, 3G: wheat 0 0 281832

Table XIII - continued

Pre-emergence efficiency (Fallsington clay-sandy soil) CH, 0 3? /

V-ni + c-nh-sc-O

CH 2 CH 2 CH 2 CH 2 O

<img img-format="tif" img-content="drawing" file="CS261852B2D01201.tif" id="idf0176" />

dose kg / ha 1/16 1/4 clover 0 5G beetroot 0 7G, 4C sorghum 8G 10C oat grain 3G 6G sorghum haleb 0 6G paspalum 0 0 beer 0 6G leek 8G 10E brome 3G 6G sugar beet 9G, 9C 10C corn 5G, 3H 7G, 8H mustard 10C 10C 8G, 5H 8G 8C 8C 8G, 5C 8G, 8C 7G 7G 8G, 5C 8G, 5C 8G, 5C 10C 10C 10C 10C 10C 10C 10C 7G, 7H rice 6G, 3C 6G, 3C wheat 0 0 73

Test C

In the bowls filled with the Fallsington Dumpster soils, seedlings, cotton, maize, rice, wheat, year-old, lucerne, Abutilon theo-phrasti, Sesbania exaltata, Cassia torus, Ipomoea spp., Datura stramonium, Xnnthium pemnsylvanicum, Digitaria spp., Cyperus rotunda, Echinochloa crusgalli, Setaria faberii, (Avena fatua).

About 2 1/2 weeks after planting, the plants and the soil around them were evenly sprayed all the way with a solution of the compound described in Example 1 in a non-phytotoxic solvent. Other groups of all above-mentioned weeds and crop plants were sprayed with the same non-phytotoxic solvent alone and served as control plants. Fourteen days after treatment, all plants sprayed with chemical agents were compared with control plants sprayed with a non-phytotoxic solvent, and vials were evaluated for the treatment of the plants for treatment; the observed data are shown in the following Table XIV. The test shows that the wheat exhibits lower levels of the number of compounds listed in this table.

Table XIV Surface Treatment and Sheet Surface Treatment S-CH-CH-CH- dose kg / ha

C-QCH2H-Q 1/16 1/4 soybean 10G 8C. 10G 7C 10C 10C 10C 10C 10C 9C 10C 10G 10C 7C 10G 6C 10G 7C 10G 7C 10C 10G 7C 10C 7C 10C 7C 10C 7C 10C 7C 10C 7C 10C 7C 10C 8C 10G. 7C, Beetle 10G 8C ......... ". __________________ ídG ..; 9C wheat 10G 7C 10G 7C beer 10G 7C 10G. 8C oat deaf 10G 8C 10G -90 / sorghum 10G 9C 10G 80 261852

<img img-format="tif" img-content="drawing" file="CS261852B2D01221.tif" id="idf0177" />

Table XIV - continued Surface treatment on soil and leaf

<img img-format="tif" img-content="drawing" file="CS261852B2D01222.tif" id="idf0178" />

1C00 1/250 soybean 10G, 8C 10G, 9C potato 10C 10C 8G, 7C 10G, 8C cassia 8G, 3C 10G, 8C cotton 10G, 7C 10C rack 2G 6G alfalfa 5G 10G, 6C durman 3G 8G , 3C 10G 8G, 2C maize 10G, 7C 8G, 3U 5G 5G 5G 5G 10G, 4C 8G, 2C 10G, 3C 10G, 10C 10C, 10C 10C, 10C 10C, 8C 8G 8G 8G oat, 3C 8G sorghum 10G, 3C 10G, 4C Table XIV - continued Soil and leaf treatment 1/128

10G, 9C10C

10G, 9C10G, 6C10G, 9C7G, 3C10G, 5C10C

10G, 8C1OG, 9C

6G

10G, 5C10C

10G, 8C10G, 4C1OG, 7C10G, 5C1OG, 7C

<img img-format="tif" img-content="drawing" file="CS261852B2D01223.tif" id="idf0179" />

CH30fi 0 dose kg / ha 1/64 1/32

soya 10G, 8C velvetleaf 10G, 8C sesbania 10G, 9C cassia 10G, 8C cotton 10G, 8C morningglory 10G, 9C alfalfa 10G, 8C datura 10G, 9C cocklebur 10G, 7C Corn 10G, 9C crabgrass 6G rice 10G, 6C nutsedge 10G, 8C shrimp 10G, 9C wheat 10G, 9C beer 10G, 9C oat deaf 10G, 7C sorghum 10G, 8C

10G, 8C10C

10G, 9C1OG, 8C10G, 8C10G, 9C10G, 8C10C1OC

1OG, 8C1OG, 4C1OG, 6C1OG, 9C1OG, 9C1OG, 7C1OG, 9C10G, 7C1QG, 8Q 261852

Table XIV - continued Surface treatment on soil and leaf

<img img-format="tif" img-content="drawing" file="CS261852B2D01231.tif" id="idf0180" />

kg 1/16 1/16 1/16 1/16 soy 10G, 9C 10G, 9C 10G, 8C 10C 10C, 10C, 10C, 10C 10G, 9C 10G, 9C 10G, 9C 10G, 9C 10G, 10C cotton 10G, 7C 10G, 9C 10C, 7C 10G, 9C 10C, 7C 10G, 9C 10C 10C, 9C 10C, 9C 10C 10C, 9C 10C 10C 10C, 9C 10C, 5C rice 10G, 3C 10G, 4C 10G, 6C 10G, 6C 10G, 6C 1G, 6C 10G, 6C 1OG, 8C 10G, 9C 10G, 7C 10G, 9C wheat 10G, 8C 10G, 7C 10C, deaf 10G, 7C 10G, 9C 10G, 8C sorghum 10G, 7C 10G, 7C 1OG, 9C

Table XIV - continued Surface treatment on soil and leaf

kg / ha ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ ^ , 9C 1OG, 9C cassette 10G, 8C 1OC 1OG, 9C cotton 10G, 6C 10G, 6C 1OG, 8C rectangle 1OC 1OC 1OG, 9C alfalfa 10G, 9C 1OG, 9C 10G, 9C durman. 10C 1OC 1OC 1OC 10C, 1C, 1C, 7C 10G, 8C 1OG, 8C 4G 5G, 2C 3G, 2C 1OG, 4C 1OG, 4C 10G, 4C 1OG, 9C 1OG, 9C 1OG, 9C 1OG, 7C 1OG , 9C 1OG, 8C wheat 8G, 3C 10G, 7C 10G, 8C beer 1OG, 9C 1OG, 9C 10C oat deaf 1OG, 6C 1OG, 5C 8G, 4C sorghum 1OG, 8C 1OG, 9C 1OG, 9G 261852

Table XIV - continued Treatment on soil and leaf surface

<img img-format="tif" img-content="drawing" file="CS261852B2D01241.tif" id="idf0181" />

O

SO2 NU-C-NU

<img img-format="tif" img-content="drawing" file="CS261852B2D01242.tif" id="idf0182" />

kg 1/16 1/16 1/16 soy 10G, 8C 10G, 8C 10G, 9C 10C, 10C, 10C 10C, 10C, 9C 10G, 9C 10G, 9C 10G, 5C 10G, 8C 10G, 8C 10C, 10C 10C, 8C 10C, 8C 10G, 9C 10G, 9C durman 10C 10C 10C, 10C, 10C 10C, 10C 10C 10C maize 9G, 3C 10G, 8C 10G, 7G 10G, 2C 10G, 2C 10G, 7C 10G, 4C 2G 10G, 5C 10G, 6C 10G, 7C wheat 7G, 3H 5G 5G 10G, 2C 10G, 7C 10G, 4C oat 6G 10G, 2C 1OG, 3C Sorghum 10G, 2C 10G, 5C 10G, 5C

Table XIV - continued Treatment on soil surface and leaf OCH,

OII-so-nh-cn HCOCH%

<img img-format="tif" img-content="drawing" file="CS261852B2D01243.tif" id="idf0183" />

<img img-format="tif" img-content="drawing" file="CS261852B2D01244.tif" id="idf0184" />

QCH-i

dose kg / ha 1/64 1/32 ...... -........- 1/16 soybean 10G, 8C 10G, 8C 10G, 8C sunflower - -. 10C 10G, 9C 1OG, 9C 10G, 9C cassette 10G, 8C 10G, 8C 10G, 8C 10G, 5C 1OG, 9C 10G, 8C 10G, 9C 10C 10C alfalfa - 8G, 6C 10G, 6C durman 10G, 9C 1OC 10C 10G, 2C 1OG, 7C 10G, 9C corn 8G, 4H 8G, 2C 9G, 4C rudder 0 0 2G rice 6G 1OG, 2C 1OG, 3C shingle 0 0 5G, 2C shrimp 6G, 2H 9G, 3H 10G, 5H wheat 3G. 2H 3G 3G beer 3G 7G 10G, 3G oat deaf 0 2G 3G, 2C sorghum 5G, 2H 1OG, 4H 10G, 4H 281852

Table XIV continued · Surface treatment on soil and leaf

<img img-format="tif" img-content="drawing" file="CS261852B2D01251.tif" id="idf0185" />

Dose kg / ha 1/16 soybean 10G, 8C potato 5G seed 10C cassia 10G, 8C cotton 5G, 2C raspberry 4G alfalfa 2C durman 4G, 2C rape 3G, 3C corn 6G, 3H rash 10 grain 10G, 10G, 4C wheat 8G beer 5G oats deaf 5G sorghum 10G, 6 ·; Table XIV - continued 1? 4

10G, 9C10C10C

10G, 8C7G, 3H9G, 3C10G, 6C6G, 2C9G, 6C10G, 7C2G

10G, 7C10G, 3C10G, 5C10G 80

8G

10G, 6C Surface treatment on soil and leaf. 0'-S (R) -nh-1'-nh- (o

<img img-format="tif" img-content="drawing" file="CS261852B2D01252.tif" id="idf0186" />

CGONa cH3 dose kg / ha 1/32 1/16 soybean 0 0 prawn 0 0 sowing 0 3G cassia 0 0 cotton 0 0 reef 0 0 alfalfa 0 0 durman 0 0 rapeseed 0 0 maize 0 0 rum 0 0 rice 0 3G shepherd 0 3G beetle 0 0 wheat 0 0 beer 0 0 oats deaf 0 0 sorghum 0 4G 1/4

5G, 205G7G

5G, 3C5G5G3G2G3G 8G, &amp; lt; / RTI &amp; gt; 5H0

8G

8G

4G

4G

2G

3G

8G, 3H

AND

Table XIV - continued Surface / soil treatment per sheet

CHA jM-CWCCW3) and

Q

NH-C-NH-SO2H2O

<img img-format="tif" img-content="drawing" file="CS261852B2D01261.tif" id="idf0187" />

CH, 0kg / ha tl / 32 1/16 1/4 soybean 10G, 8C 10G, 8C 10C 1C 10C 10C 10C 10C 10C 10C cassette 10G, 8C 10G, 8C 10G.-9C cotton -1 -10C 10C 10C 10C 10C 10C 10C alfalfa 10C 10C 10C 10C 10C 10C 10C maize 10C 10C maize 8G 3HG 10G 3C 10G 8C 5G 5G 9G 3C rice dOG 6C 10G, 4C 10G, 8C 10G, 9C 10G, 8C 10G, 9C 10G, 9C wheat Ó8G 10G 10G, 3H 10G 10G 10G 10G, 3C 10G 10G 10G 10G, 10C 10G 10G, 10C, 10C 10G, 8C Table XIV - continued

Surface treatment of the soil and on the surface of the soil, C-O-CH (CW3) 2, C (O) CH3 (CH2)

dose kg / ha 1/32 1/16 1/4 soybean 10G, 8C 10G, 8C 10G, 8C potato 10C 1OC -. harvest 10G, 9C 1OC 10C cassette 10G, 8C 10G, 8C 1OG, 8C cotton 10C 1OC 1OC 1ch 10C 1OC 1OC alfalfa 1OC 1OC 10C durman 10C 1OC 10C 10G, 9C 10C 1OC corn 8G, 3C 7G, 3C 10G, 9C 8G 8G 10G, 8C 10G, 6C 10G, 4C 1G, 5C 10G, 4C 1G, 5C 10G, 8C 8G, 3C 1QG, 8C 10G, 8C 10G, 6C 10G, 8C 10G, 6C oats deaf 10G 10G, 3C 10G, 5C sorghum 1OG, 4C 10G, 3C 10G, 8C

Table XIV - continued 261852 Surface treatment of the soil q-CO-CH (CH3) 2 / HC? % -NH- [-NH-SO2NH2-

CH-iO dose kg / ha 1/32 1/16 1/4 soybean 10G, 8C 10G, 9C 10G, 8C 10C 10C, 10C, 10C, 10C 10C, 10C 10C 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 8C, 8G, 3H 8G, 3H wheat 0 0 0 beer 2G 0 5G oat deaf 5G 5G 8G sorghum 8G, 3H 10G, 3H 1OG, 3H Table XIV - continued Soil and leaf treatment

<img img-format="tif" img-content="drawing" file="CS261852B2D01271.tif" id="idf0188" />

dose kg / ha 1/32 1/16 1/4 10G, 8C 10C 1OG, 9C 10C 10C 10C 10C 10C 10C 10C 10C 10C, 10C, 9C 10C, 9C 10C, 9C 10C, 9C 10C 10C 10C 10C 1C 10G 10C 10C 10G 10C 1C 10C 10C 10C 1C 10C 1C 10C 1C 10C 1C 10C 1C 10C 10C 10C 10C 7C 10G 7C 1OG 7C 1C 7C 1C 10C 10C, 8C 10G, 7C 10G, 9C wheat 8G 10G, 3C 10G, 4C beer 7G 10G 1OG, 3C oat deaf 1OG, 6C 10G, 5C 10G, 7C Sorghum 1OC 10G, 8C JffiQC 26 1 8 5 2

Table XIV - Continued Treatment on soil surface and leaflet ch3ox / CH- ^ -NH-À-NH-SOj / θ CN λ- * dose kg / ha 1/32 1/16 soy 10G, 3C 1OG, 6C potato 10G, 7C 10C sinking 10G, 5C 10G, 7C cassia 3G 4G cotton 10G, 4C - rack 1OG, 3B 1OG, 5B alfalfa 10G, 6C 1OG, 6C durman 8G, 3C 8G, 3C grain 10G, 4C 10G, 6C corn 5G, 2H 8G , 3G wheat 0 0 rice 8G 1OG, 2C rake 3G 8G beetle 8G, 2C 10G, 3C wheat 0 3G beer 7G 7G oat deaf 6G 7G sorghum 5G 1OG, 3H Table XIV - continued 1/4

10G, 6C10C

10G, 8C8G, 3C10G, 8C

10B 10G, 9C10G, 6C10G, 6C10G, 3H0

10G, 4C9G

10G, 3C5G

1OG, 3H9G

10G, 3H Surface treatment and leaf treatment

<img img-format="tif" img-content="drawing" file="CS261852B2D01281.tif" id="idf0189" />

dose kg / ha 1/16 1/4

soy 10G, 9G potato 10C seed 10C cassia 10C cotton 10C raspberries 1OC alfalfa 10C durman 10G, 6C sprout 10C maize 10G, 2C ratchet 4G rice 7G maize 8G, 3C rake 7G wheat 0 beer 0 oats deaf 3G sorghum 8G. 5H

1OG. 9C

10C

10G, 9C10C10C10C

10G, 7C10C

10G, 8C7G

10G, 2C10C

1OG, 3C3G7G8G 8G, 20 281852

Table XIV - continued Surface treatment and soil c = o, WH-C-NM-SO / O,

cH3 ^ CÍ-CH2CH2-0 ~ C0 dose kg / hasoja mrakňák harvest cassia cotton clover alfalfa durman spelled corn russe rice rye barley wheat beer oats dehumidifier lj / 16 1/4

10G, 9C 10G, 9C 10C - 10G, 9C 10G, 8C 10C 10C 10G, 8C 10G, 9C 10C 10C 10G, 9G 10C 8G, 3C 10G, 5C 1CC 10C 8G, 20G, 2G 5G 8G, 2C 10G, 4G 10G , 5C 10G, 6C 10G, 6C 10G, 7C 10G, 8C 6G 10G 10G, 7C 10G, 9G 8G 10G, 3C 10G 10G

Table XIV continued Treatment on Soil and Sheet 2 &lt;C-ty 0

Yr-NW-C-NH-SO2-OH

<img img-format="tif" img-content="drawing" file="CS261852B2D01291.tif" id="idf0190" />

/ RTI &amp; gt;

* * II 0 dose kg / hasoja sunflower harvesting cassia cotton clover alfalfa durman shrimp corn rushes rice ryegrass shrimp wheat beer oats dehumidifier 1/16 1/4

10G, 9C 10G, 9C 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 10C, 8C 10G, 8C 10G. 8C 10G 10G, 4C 10G, 3C 10G, 9C 10G, 2C 10G, 2C 10G 10G, 2G 281852

Table XIV dose kg / hasoia sunflower harvesting cassia cottony alfalfa alfalfa durman spelled corn ruby ​​rice ryegrass shrimp wheat beer oats dehumidifiers continued Treatment on soil and leaf surface cH3O-NH-C-NH-SO / Z Cl-CH -CH-O-CCH3G2 2 g 1/16

10G, 9C

10C

10G, 9C10G, 9C10C5G

8G, 4C10C5G3G4G 10G, 4C7G000

6G

Table XIV continued 1/4

10G, 9C10C10C10C

10G, 8C10C

10G, 9C10G, 4G

8G, 2C4G6G 10G, 4C8G00

5G

8G dose kg / hasoja sunflower cassia cassia cotton alfalfa alfalfa durman spelled corn russe rice ryegrass shrimp wheat beer oats dehumidifiers Surface treatment of soil and leaf

<img img-format="tif" img-content="drawing" file="CS261852B2D01301.tif" id="idf0191" />

10G, 9C 10G, 9C 10C - 10C 10C 10G, 9C 10C 10G, 8C 10G, 9C 10C 10C 10C 10C 10G, 5C 10G, 8C 10C 10C 10G, 3H 1OG, 3C 0 3G 4G 7G 5G 9G, 4C 6G 8G 0 0 0 3G 3G 5G 10G, 3H 10G 1/4 261852

Table XIV - continued Surface treatment on soil and leaf

<img img-format="tif" img-content="drawing" file="CS261852B2D01311.tif" id="idf0192" />

1C 10G, 9C 10G, 9C 10G, 9C 10G, 9C 10C, 9C 10C, 9C 10C, 9C 10C, 9C 10C, 10C, 9C 10G, 6C beet 10C 10C corn 4G 7G, 3H slice 0 4G rice 10G, 3C 10G, 3C shingle 10G, 5C 10G, 8C shrimp 10G, 3H 10G, 4C wheat 2G 7G beer 0 5G, 2C oat deaf 5G 8G, 3H sorghum 10G 10G, 2C Table XIV - continued Surface treatment on soil and leaf ---------------------- - -

<img img-format="tif" img-content="drawing" file="CS261852B2D01312.tif" id="idf0193" />

1C 10G, 7C 10C, 10C, 10C, 9C 10G, 7C 10G, 9C 10G, 7C 10G, 9C 10G, 7C 10G, 9C 10G, 7C 10G, 9C durman 10G, 8C 10G, 8C 10C 10G 10C, 9C 10G, 5H 8G, 5C 8G, 2C 1G, 8G 7G, 2C 7G, 3C 8G, 3C 1OG, 6C wheat 4G 8G beer 2G 6G oats deaf 10G 8G, 3C Sorghum 10G 10G 261852 77 78

Test D

The high herbicidal activity of one of the compounds of formula I included in the scope of this invention is evident from the results obtained in this assay. The test relates to the pre-emergence effect of the substance when applied to the soil surface. Plastic pots of 25 cm in diameter, filled with Fallsington clay-sandy soil, were used as culture vessels. One row of flower buds was seeded with weed seeds that would be evenly mixed with the top, 1.2 cm high layer of the earth. The following weed species were used for testing: Sorghum halepense, Echinochloa crusgalli, Digitaria sanguinalis, Setaria faberii, Abutilon theophrasti, Durman (Datura stramionium), Mustard (Brassica arvensis) and bent beetle (Amaranthus retroflexusj.

Another row of pots was seeded by the following crops, in a quantity of one to four species per pot: corn (depth of sowing 3.7 cm), cotton, soybean, sunflower, Clinton oat, black Valentine, rice, (all 2.5 cm), cucumbers, cabbage, alfalfa, safflower, sugar beet, tomatoes, spinach, barley and Kentucky lip (all at a depth of 1.2 cm). The seed solution was seeded on the surface of the pots with a solution of the test compound in a non-phytotoxic solvent.

After one pot of each type and one for each type of plant, the plants were left untreated for comparison purposes. Treated and unspoiled flower pots were quickly irrigated with simulated rainfall at about 4 mm precipitation, and then left for several weeks in a glasshouse. At 28 days post-treatment, the weeds of the weeds and the plants were visually evaluated for chemical use using the evaluation system described above in Assay A. The data obtained are shown in the following Table XV.

Table XV

Pre-emergence application on soil surface dose kg / ha

<img img-format="tif" img-content="drawing" file="CS261852B2D01321.tif" id="idf0194" />

1/64 1/32 1/16 1/8 corn - cotton - soybean - groundnuts - sunflower - oats - wheat - sorghum - sugar beet - peas - lentils - alfalfa - beans - spinach - cabbage - tomato - . - cucumbers - leeks - barley - tsbak

broadband 7G 5C

grass 6G

- - 10C

- 9G 9C

- - 9G 9H

- - 10E

- - 8G 7C

- - 8G 9C

- - 10C

- - 10C

- - 10C

- - 10C

- - 10E

- - 10C

- - 7G 8H

- - 10C

- - 10C

- 8G 8C

- - 10E

- 9G 9C

- - 8G 7C

- - 10C

- - 9G 8C

- - 5G 2C 8G 8C 9G 8C - 8G 6C 8G 8C - 2 B 1 8 5 2 79

Test E

This test, carried out in the greenhouse-prokaryotic, we consider the application of certain compounds as shown in formula I included in the scope of this invention-for the preemergence and postemergence control the growth of broadleaf weeds dru-hu and Shakhtar in young kulturáchpšenice and barley. As a culture container, 25 cm plastic pots filled with fertilized Fallsington sandwich are used. In pots were sown seeds on-pursuing weed species, twice, vdesetidenním interval: mustard (Brassica arvensis), cocklebur (Xanthium spp.J, morning glory (Ipomoea hederacoa), cassia (Cassia Toraja, velvetleaf (Abutilon theophrasti), alfalfa ( used as indicator species) metlovitý kochia (Kochia scciparia) Sesbania (Sesbania exaltata), Ruthenian thistle (Salsola Kali), datura (Datura) ašáchor (Cyperus rotundus).

Table XVI 80 In addition, other 15 cm diameter plastic pots filled with the same soil were planted with wheat and barley, and the pots were poured once in the first sowing of the weeds. All flower pots were treated with test chemical compounds dissolved in a non-phytotoxic solvent immediately after the end of the first weeding of weed seeds. In the present period wheat was about 15 to 17.5 cm tall and barley about 12.5 to 15 cm tall, both plant species in the growth stage of the second leaf. Individual types of weeds from prior sowing were 2.5 to 12.5 cm high. The applied application rates were 0.004, 0.007, 0.015 and 0.030 kg / ha for weed treatment, and 0.12, 0.25 and 0.50 kg / ha for wheat and herb treatment. The reaction of test plants treated post-emergence was visually assessed 21 days after spraying, the response of pre-emergence weeds to 28 days of treatment. For evaluation, the scales described above in Test A were used. The yields are summarized in the following Table XVI.

Pre-emergence applications, Fallsington soil O n / OCH3 'C00- \ OCH.

dose kg / ha 1/256 1/128 1/64 1/32 mustard 9G 9C 10C 10C 10C rapeseed 7G 7H 8G 8H 8G 8H 8G 9H rack 8G 7C 8G 7C 8G 7C 8G 9C cassia 8G 5C 8G 5C 8G 5C 8G 8C 8G 3H 8G 3H 8G 5H 9G 5H alfalfa 5G 5G 2C 5G 8G 7G 7G 7G 3G 8G 9C 8G 9C 9G 9C 9C 9C 9C 10C 10C 10C thistle 5C 7C 7C 7C 9C 9C 7G 8C 8G 7G 8G 9G 10C 26C

Table XVI - continued

Pre-emergence applications, Fallsington soil CH, SO2NH-C-COOCH3

kg 1/256 1/128 li / 64 1/32 mustard 10C 10C 10C 10G 8G 8C 8G 8G 8H 8G 8H 8G 9H 8G 8C 9G 9C 10C 10C 8G 8C 8G 8C 8G 9C 8G 9C 9C 10C 10C alfalfa 7G 7G 7G 2C 9G 8C 9G 7C 7G 7C 3C 7G 5C 8G 8C 10C 9C 9C 10C 10C 10C thistle 7C 8C 10C 10C durman 7G 6C 7G 5C 8G 9C 8G 7C 6G 3C 7G 2C 8G 8G

Table XVI - continued

Post-emergence applications

<img img-format="tif" img-content="drawing" file="CS261852B2D01341.tif" id="idf0195" />

dose kg / ha 1/256 1/128 1/64 1/32 mustard chop 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10G - thistle 8C 10C 10C 10C durman 7G 5C 10G 5C 10G 7C 10G 6C 7G 3C 10G 8C 10G 5C 10G dose kg / ha li / 8 1/4 1/2 wheat 2G 2G 2C 6G 3C barley 0 6G 2C 8G 3C 261852 81 82

Table XVI - continued

Post-emergence applications of CH,

<img img-format="tif" img-content="drawing" file="CS261852B2D01351.tif" id="idf0196" />

SO 2 NH- {Qn 2 N-z co-z OCH 2,

dose kg / ha 1/256 1/128 1/64 1/32 mustard sprout 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C - thistle 10C 10C 10C 10C durman 10G 4C 10G 8C 10G 8C 10G 9C reed 3G 5G 3C 10G 7C 10C dose kg / ha 1/8 1/4 1/2 wheat 0 0 5G 3C barley 5G 5G 2C 7G 3C

Test F Many of the compounds of formula (I) encompassed within the scope of the invention exhibit high reactivity to the rust, as evidenced by the following testing.

Spray-treated soil was used to cover the surface of the spraying treatment by spraying. Spread-spray treatment was applied to spruce leaves and the surface of the surrounding soil after emergence of plants when they reached a height of 12 cm.

Immediately after application of soil spray, tuber and soil treatment, or post-spray application, the pots were orosed with water in about 0.3 cm rainfall in 90 minutes then placed in a greenhouse. Postemergence treatments were carried out directly on the cellar and the plants were carefully irrigated to prevent spraying from the leaves.

The reaction of the rush for the treatment of the compounds of formula (I) was evaluated 4 weeks after application; the results are shown in the following Table XVIII. 261852

Table XVIIHerbicidal efficacy against chromosome CH3x0-nh-c-nh-

\ -N

C13H13NO3

u 3 II 0 Dose Evaluation of the response of plants after 4 weeks

<img img-format="tif" img-content="drawing" file="CS261852B2D01361.tif" id="idf0197" />

kg / ha soil surface spraying tubers incorporation soil post-emergence 0,004 8E 9G 10E 10E 4C 7G 0,008 10G 10E 10E 9C 0,016 10E 10E 10E 9C 0,032 10E 10E 10E 10C 0,064 10E 10E 10E 10C

Table XVII - continuedHairbicidal efficacy against the umbilicus

<img img-format="tif" img-content="drawing" file="CS261852B2D01362.tif" id="idf0198" />

C-OCH3

<img img-format="tif" img-content="drawing" file="CS261852B2D01363.tif" id="idf0199" />

Dose Evaluation of the plant response after 4 weeks kg / ha on the soil surface Spraying tubers Post-emergence post-emergence into soil

0.004 8E 9G 10E 10E 5C 7G 0.008 10E 10E 10E 9C 0.016 10E 10E 10E 9C 0.032 10E 10E 10E 10C 0.064 10E 10E 10E 10C

Table XVII - continuedHairbicidal efficacy against the umbilicus

<img img-format="tif" img-content="drawing" file="CS261852B2D01364.tif" id="idf0200" />

Dose Evaluation of the reaction of plants after 4 weeks kg / ha on the surface of spraying post-emergence of soil into the soil

0,004 9E 9G 8E 9G 8E 9G 8C 0,008 10E 10E 10E 1OC 0,016 IOE 10E 10E 10C 0,032 10E 10E 10E 9C 0,064 10E 10E 10E 10C 261852

Table XVII - ContinuedHebicidal Efficacy against Cheddar C-OCHj

O

-SO 2 NH-C-NH

<img img-format="tif" img-content="drawing" file="CS261852B2D01371.tif" id="idf0201" />

Dose Evaluation of plant reaction after 4 weeks kg / ha on spray surface post-emergence soil posture in tubers 0,004 4C 7G 5C 8G 5C 8G 0 0,008 4C 7G 5C 8G 5C 8G 2G 0,016 4C 7G 5C 9G 5C 8G 2G 0,032 5C 8G 5C 9G 5C 9G 2C 5G 0.064 5C 8G 5C 9G 6C 9G 5C 7G, ýíSsffiSr Table XVII - continued Herbicidal Efficacy against OCH *

<img img-format="tif" img-content="drawing" file="CS261852B2D01372.tif" id="idf0202" />

N-SO2-NH-S-Qa,

<img img-format="tif" img-content="drawing" file="CS261852B2D01373.tif" id="idf0203" />

iCt-L

Dose Evaluation of the reaction of plants after 4 weeks kg / ha on the surface of spraying post-emergence soil posture into the soil 0,004 3C 6G 3C 7G 3C 7G 0 0,008 4C 8G 4C 8G 8G 4C 0 0,016 - 4C 8G 4C 8G 2C 3G 0,032 4C 8G 4C 8G 4C 8G 3G 0.064 5C 8G - 4C 8G 3C 4G

<img img-format="tif" img-content="drawing" file="CS261852B2D01381.tif" id="idf0204" />

Table XVII - continuedHerbicidal efficacy against the chewing gum

<img img-format="tif" img-content="drawing" file="CS261852B2D01382.tif" id="idf0205" />

O Dose Evaluation of plant reaction after 4 weeks kg / ha on spraying surface Post-emergence post-emergence of soil in tubers 0.032 0.125 0.5 0

2E 7GIDE

2G

4E 8G10E 0

8E 9G10E 0

9C

10E

<img img-format="tif" img-content="drawing" file="CS261852B2D01383.tif" id="idf0206" />

Table XVII - continuedHerbicidal efficacy against chisel ch3o. ch30

y = -N

<img img-format="tif" img-content="drawing" file="CS261852B2D01384.tif" id="idf0207" />

NH-C-NH-SQf (Q C2 H5 O)

Evaluation of the reaction of plants after 4 weeks spraying surface Soil incorporation of tubers into soil Dose kg / ha post-emergence

0.008 10E 10E 10E 10C 0.032 10E 10E 10E 10C 0.15 10E 10E 10E 10C 0.25 10E 10E 10E 10C

CH3O .. co {ch2 \ ch.

0.008 2C 4G 3C 7G 3C 8G 5C 7G 0.032 3C 6G 3C 7G 3C 7G 3G 6G 0.125 HC 8G 3C 8G 5E 9G 8C 0.5G 8G 5E 9G 5E 9G 5C 6G 261852

Table XVII - continuedHairbicidal efficacy against the umbilicus

<img img-format="tif" img-content="drawing" file="CS261852B2D01391.tif" id="idf0208" />

Dose Evaluation of plant reaction after 4 weeks kg / ha on spray surface Post-emergence post-emergence soil hillious soil 0,004 0,008 0,016 0,32

8G

8G

8E 9G5E 9G

7G

8G

6E 9G8E 9G

8G

8G

8E 9G10E

8C

9C

9C

10C

O

(CH3) 2 --CH2 --CH2 --CH2 --CH2 --CH2 --CH2 --CH2 --CH2 CH2 -

NH ~ C ~ NH ~ S

Cl-L

0.008 10E 10E 9E 9G 10C 0.032 10E 10E 10E 10C 0.125 10E 10E 10E 10C 0.25 10E 10E 10E 10C

Table XVII - continuedHairbicidal efficacy against the umbilicus

10-CH 2 -NH-C-NH-SO 2 -O-

-No dose kg / ha ch3o

Evaluation of plant reaction after 4 week surface spraying surface of tubers soil into soil post-emergence 0.008 IDE 10E 10E 10C 0.032 10E 10E 10E 10C 0.125 10E 10E 10E 10C 0.25 10E IDE 10E 10C 0 CH.O S-OCHO

CH3O 0.008 3G 4G 5G 3G 0.032 7G 7G 7G 5C 6G 0.125 9G 9G 9G 10C 261852 83

Table XVII - continuedHebicidal Efficacy against the Rhizo

Coco C-NH-S-Dose Evaluation of the reaction of plants after 4 weeks kg / ha on the surface of the post-emergence post-emergence of soil into the soil

0.008 2C 5G 7G 7G 2C 5G 0.032 9G 10E 8E 9G 9C 0.125 10E 10E 10E 9C ch30,

C-OCH2-N-NH-C-NH-SO2NH2

CH 2 O

0.008 8E 9C 10E 10E 10C 0.032 10E 10E 10E 10C 0.125 10E 10E 10E 10C

Test G

Tubers of purple nutsedge (Cyperus rotun-DUS, L.) were planted about 2 cm hlubokojednak Fallsingtonské into sandy loam soil PU derived from Delaware (content-limiting about 1% organic matter / OH / - nízkýobsah OH), and secondly to Flanaganské clay from Illinois (containing about 4% organic matter - high OH content).

A total of five tubers were planted in each 10 cm plastic pot. The chemical treatment was carried out in the manner described in Table XVII in three different ways: by spraying on the surface of the soil, spraying on soil and soil, and incorporating the spray into the ground. When sprayed onto the soil surface, the test chemical was sprayed onto the suffocated surface of the soil after the tubers have been planted, but still before their germination. When applied to the soil and soil, the solution of the test compound was sprayed with the tuberous tuber and the soil with the wheel before the tubers were covered with untreated ground. Spray-treated soil was used to treat tubers by spraying the tubers.

Immediately after the aforementioned test compounds, the pots were orosized with water at 0.3 ° C for 90 minutes and then placed in a greenhouse. From the results of the evaluation of the plant reaction for the weeks following the treatment, as shown in the following table XVIII, a high degree of efficacy of the test compounds is evident. Z 6 1 8 5 2 8i

Table XVIII 86

Evaluation of the reaction of the shingles in 4 weeks after treatment.

<img img-format="tif" img-content="drawing" file="CS261852B2D01411.tif" id="idf0209" />

ch3 Dose kg / ha

Spraying the surface of the soil

Spraying on tubers and soil

Spraying the soil

low OH high OH low OH high OH low OH high OH 0.008 10E 4C 7G 10E 7E 9G 10E 9E, 9G 0.016 10E 8E 8G 10E 10E 10E 8E 9G 0.032 10E 9E 9G 10E 10E 10E IDE 0 c ~ oc O Cos, OCT, 0.008 0.016 0.032 5C 8G 0

9E 9G 2C 4G

10E 10C

9E 9G10E10E

5E 7G10E

9E 10C

8E 9C 2C 3G

9E 3G 3C 3G

10C 7E 3C 8G

Test H

Two 25.4 cm diameter plastic dishes, divided by polyethylene bumpers, were filled with prepared Fal-lsington clay-sandy soil. The species were sown with seeds of wheat (Triticum aestivum), barley (Hcrdeum vulgare), Avena fatua, Bromus tectorum, Bromus secalinus, Alopecurus myosuroides, Poa annua, , the green beard (Setaria viridis), the creeping pheasant (Agropyrum repensj, the Lolium multiflorum) of the caterpillar (Bromus rigidus).

The second bowl was seeded with buckwheat seeds (Polygons covolvulus), the calf (Kochia scoparia), the pineapple (Polygons pennsylvanicum), the sea weevil (Matricaria inodora), the Sisymbrium altisusum, the mustard Brassica kaber, Descurainia pinnata, Amaranthus retroflexus and Salsolacalis salmonella.

The two dishes were pre-treated. At the same time, the same twins, in which the above-mentioned plant species were grown, were treated post-emergence; plant height at the time of treatment ranged from 1 to 15 cm, depending on the plant species.

The test compounds of the formula (I) were dissolved in a non-phytotoxic solvent and the solution was sprayed on top of the seeds with seeds or plants. The comparison included untreated controls and controls treated with the solvent itself. All the pots treated with the plants were then grown for 20 days in the greenhouse. After this time the treated plants were compared with the controls and the treatment was visually evaluated. Got it. the data are shown in the following table XIX. From the results it is again apparent that some of the test compounds of general formula I can be used to control the growth of weeds in wheat and barley crops. ZB1852

Table CHIC CHi

&gt; NH

O-c-nh-so2

<img img-format="tif" img-content="drawing" file="CS261852B2D01421.tif" id="idf0210" />

Dose kg / ha 1/16 of 1/8 pre-emergence

wheat 9E 9G 9E 8G barley 7H 8G 8H 8G oat deaf 4H 7G 7H 8G bark roof 9E 9G 10E borage 7G 8G 9E 9G 9G 9H 9G 9H 9G 8H 8G 8G 9G 8G 8G 8G 8G 8G 8G 9G 7G 7G 7H 8G 6k 7G 8H 8G 8G 9G 10C Buckwheat 8C 9G 10C Buckwheat 4C 7G 5C 8G 9C 9G 9G 9G 9C 9G 9G 9G 9C 9G 9C 9C 9C 9C 9C 9C 9G 9C 9G 9G 9C 9G 9G

10C

8C 9G7C 7G

10C

10C

8C 8G

Table XIX - continued ch3

OY-nh-c-nh-so-O-N-CM,

O

II CHaO-Cu ii

O Dose kg / ha 1/16 1/8

post-emergence wheat 9C 10C barley 9C 10C oats deaf 9C 10C bark 10C 10C 10C 10C bark 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C rdesno 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C

Table XIX - continued ch * ° \ -no

NQ) -NH (NH3) -SO3) -NH3

<img img-format="tif" img-content="drawing" file="CS261852B2D01431.tif" id="idf0211" />

(CH3) z

Dose kg / ha 1/64 1/32 1/16 pre-emergence wheat 0 0 0 barley 0 0 0 oat deaf 0 0 0 bark roof 0 0 1G cereal bark 0 0 1G pike scallop 0 0 2G grasshopper annual 0 0 1G green beer 0 0 1G creeper beetle 0 0 0 leeks multicolour 0 0 0 bell pepper 0 0 0 buckwheat braid 3C 5G 7C 8G 7C 8G flat whale 5C 7G 7C 8G 9C rosewood 4C 7G 10C 10C chamomile false 9G 9G 9G raccoon highest 10C 10C 10C mustard flat 10C 10C 10C Eagle 7C 9G 10C 10C Blower 7G 5C 8G 10C Potassium Salt 3G 4G 7C 5G

Table XIX - continued * ch3o,

CO-CH

<img img-format="tif" img-content="drawing" file="CS261852B2D01432.tif" id="idf0212" />

NH2-NH-C-NH-SO2 (Q)

CHaO

Dose kg / ha 1/64 1/32 1/16 post-emergence wheat 0 0 1C barley 0 0 0 oat deaf 0 0 1C bark roof 0 0 0 brome cereal u 0 0 grasshopper 0 0 0 grasshopper annual 0 0 2G beer green 1C 1C 2C 3 (creeping beak 0 0 0 leafy mullet 0 0 0 bark beeed 0 0 0 foot opal 9C 10C 10C flat whale 10C 10C 10C rosewood 9C 9C 10C chamomile false 10C 1OC 10C raccoon highest 10C 10C 1OC mustard flat 10C 10C 10C thistle 10C 10C 10C bent beetle 9C 10C 1OC potassium saltplate 9C 10C 10C 261852

Table XIX - continued

<img img-format="tif" img-content="drawing" file="CS261852B2D01441.tif" id="idf0213" />

Dose kg / ha 1/64 1/32 1/16 pre-emergence wheat 0 0 0 barley 0 1G 1G oyster deaf 0 2G 3G bark roof 1G 3G 5G cereal bark 1C 2G 1C 3G 2C 4G 2G 3G 4G grasshopper annual 2G 3G 5G beer green 0 0 1G creeping beetle 0 0 2G leafy mullet 0 2G 3G bell pepper 0 0 0 buckwheat braid 9C 9C 10C whale blossom 9C 10C 10C rosewood 9C 10C 10C chamomile false 9G 9G 1OC raccoon highest 10C 10C 10C mustard flat 10C 10C 10C stomach 10C 10C 10C bent beetle 8C 9C 10C potassium saltpeter 3C 5G 7C 7G 8C 8G Table XIX - continued 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

Dose kg / ha 1/64 1/32 1/16 post-emergence wheat 0 0 1C barley 0 0 0 oat deaf 0 0 2C bark roof 0 0 2G cereal bark 0 0 1C 2t grass fescue 0 0 2G grasshopper annual 0 0 3G beer green 0 1G 3C creeper 0 0 1G yolk multicolored 0 0 2G buckwheat bushy 0 0 0 buckwheat braid 10C 10C 10C collar 10C 10C 10C 10x 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C 10C bent beetle 10G 10C 10C 10C 10C 10C 10C 10C 261852 87 88

Test I

Plastic pots on průměru12,7 cm were filled with a mixture Fallsingtonskéhlinito-sandy ground with sand in a ratio of 1 :: 1, and in this land were sown the seeds on pursuing-weed (one kind of skin-vele per pot): milkweed Mortiere odorata, Plantago spp, Arctium minus, Convolvulus arvensis, Taraxacum ofíicinale, Solanum carolincnse, Cynodon dactylon, Agropyron repens, , paspalum (Paspalum dilatatum) and Hawthorn (Sorghum halepense).

The flower pots were placed in the greenhouse and the plants were grown for several weeks.

Test compounds of the formula were dissolved in a non-phytotoxic solvent and the plants were sprayed onto the sheet. For comparison, untreated control plants and plants were examined alone with the solvent alone. The effect of test compounds on plant growth was evaluated and evaluated eight weeks after treatment. The results of the evaluation are summarized in the following Table XX. The data provided show high efficacy of test compounds to control the growth of extruded, long-lived broadleaf weeds of iplevel grass.

Table XX Effectiveness against persistent broadleaf and grass weeds

<img img-format="tif" img-content="drawing" file="CS261852B2D01451.tif" id="idf0214" />

Plant species after 1 1/8 kg / ha Evaluation of the plant reaction week 1/4 kg / ha after 8 weeks 1/8 kg / ha 1/4 kg / ha of wheat 0 0 10C 10C seedlings 0 0 10C 10C burdock less 0 0 4C 10C scallop 0 2C 7C 8C dandelion 0 0 10C 10C eggplant 0 1C 5C 10C scallop 5C 6C 5C 7G 6C 8G creep 6C 7C 10C 10C paspalum 6C 6C 8C 8G 10C HACCP sorrel 8C 9C 10C 10C Test J after treatment the surface was irrigated with water ''

The high herbicidal efficacy of one of the compounds of formula I included within the scope of this invention has been confirmed by polistem. The substance was applied preemergently to the surface of clay-sandy soil. In three days

an amount corresponding to 2.5 cm of precipitation. Numerous weeks have been evaluated for suppression of growth of individual plant species in percentages; the results are shown in the following table XXL È9 261852 90

Table XXI Effectiveness at pre-emergence treatment of crop plants and weeds in the field of the growth of plants (O) -NH-NH-s-O-CH-CH.

Plant species Untreated 0.031 crabgrass 0100 foxtail 0100 nutsedge 0 98 Redroot 0100 faucet foxtail 0100 velvetleaf 0 98 goosefoot 0100 purslane 0100 smartweed 0100 barnyardgrass 0100 ryegrass 0100 oat 0 98 spinach 0100 only 0 90 endive 0 100 cabbage 0100 beetroot 0100 carrots 0100 beans Lima 0 50 beans garden 0 80 tomato 0100 groundnut 0 70 potato 0 90 cucumber 0100 pumpkins 0100 sugarbeet 0100 soybean 0 90 alfalfa 0100 clover 0 80 cotton 0100 oats 0 100 margins 0 90 rice 0 100 wheat 0 90 sorghum 0 100 maize 0 100 sunflower 0 70 flake dye 0 100 Dose kg / ha 0.063 0.125 0.25

Test K

The reaction of a number of harmful weed species by in-situ application of the same compound that was used in the J test was studied in another field assay. At the time of treatment, in the month after the original crop fell, the mixed vegetation grew to about 15 cm. Chemical formula applied 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 60 70 90 90 95 100 100 100 100 80 90 90 100 100 100 100 100 100 100 100 100 100 100 100 95 98 98 100 100 100 100 100 100 90 90 95 100 100 100 90 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 95 100 100 100 100 100 aqueous solution containing 0.2% surfactant ("SurfactantWKR") in a total volume of 500 liters per hectare.