Fungicidal combinations of active substances
6 claims: 4 independent, 2 dependent
- 1Active compound combinations, comprising at least one compound of the formula and (1) a triazole derivative of the formula in which X represents chlorine or phenyl and represents and/or Le A 34 16!-Foreign Countries (2) the triazole derivative of the formula and/or (3) an aniline derivative of the formula 1 —CCLF R 1 —ל ץ—Nf \=/ ^SO-N(CH 3 ) 2 in which R 1 represents hydrogen or methyl, and/or 15 (4) N-[l-(4-chloro-phenyl)-ethyl]-2,2־dichloro-l-ethyl-3-methylcyclopropane-carboxamide of the formula (carpropamid) (V) and/or Le A 34 161-Foreign Countries (5) the zinc propylene-1,2-bis-(dithiocarbamidate) of the formula • II I . II —[Zn-s—c—NH—CH—CH—NH—C-S] z ’ ;(VI) 1- < ח ' (propineb) and/or (6) at least one thiocarbamate of the formula (VII), Me = Zn or Mn or a mixture of Zn and Mn and/or (7) the aniline derivative of the formula and/or (8) the compound of the formula / 9 v <?h(ch 3)־ (CHjIjCH-O-C-NH-CH-C-NH-CH—/ י—CH 3 (IX) k ' ‘ 9 . ז ' J v׳־ I יי y . ׳ ch, .־־ □ 20 (iprovalicarb) Le A 34 161-Foreign Countries and/or (9) the benzothiadiazole derivative of the formula (acibenzolar-S-methyl) and/or (10) the 8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxa- spiro[5,4]-decane of the formula (XI) (spiroxamine) and/or (11) the compound of the formula and/or Le A 34 16!-Foreign Countries (12) the compound of the formul a (XIII) Z O H״C o (trifloxystrobin) 5 and/or (13) the compound of the formula (14) the cyanoxime derivative of the formula 00 CN CH-CH-NH-C-NH-C-C=NOCH 3 (XV) □ £u ג (cymoxanil) and/or Le A 34 161-Foreign Countries (15) a pyrimidine derivative of the formula in which (XVI), R 2 represents methyl, —C=C—CH 3 (mepanipyrim) or cyclopropyl (cyprodinyl), and/or (16) an aniline derivative of the formula ch, ,CH-COOCH, ד II > (XVII) =£V׳' r C-CH-O—CK CH ׳״ Λ ’ UM 3 0 ״ ־־ (metalaxyl or metalaxyl M) and/or (17) the morpholine derivative of the formula (XVIII) Le A 34 161-Foreign Countries and/or (18) the phthalimide derivative of the formula (XIX) (19) the phosphorus compound of the formula HO. w £. (XX) (fosetyl-AI) and/or (20) the hydroxyethyl-triazole derivative of the formula (XXI) and/or Le A 34 161-Foreign Countries (21) the l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine of the formula ch -n׳ cr N N—NO, . . . . ״ 2 (imidacloprid) and/or (22) the oxazolidinedione of the formula N H ס^׳א^׳ס (famoxadone) and/or (23) the benzamide derivative of the formula C 2 H s 0 c—CH,CI II 2 (zoxamide) and/or Le A 34 16!-Foreign Countries (24) the guanidine derivative of the formula R 3 R 3 3 I ' R-f|—(Ch ־ ( ־ -[n-(CH 2 )j-n-h (xxv) x (2 + m) CHjCOOH in which m represents integers from 0 to 5 and R 3 represents hydrogen (17 to 23%) or the radical of the formula -C=NH nh 2 (77 to 83 %) and/or (25) the triazole derivative of the formula Cl—^^—(j)H-C 3 H 7 -n CH, (XXVI) N z \ (penconazole) and/or Le A 34 161-Foreign Countries (26) the halogeno-benzimidazole of the formula N F 0 N SO 2 (XXVII) CH, o and/or (27) the halogenopyrimidine of the formula and/or CH, w (XXVIII) (28) the tetrachloro-isophthalo-dinitrile of the formula (XXIX) (chlorothalonil) and/or Le A 34 161-Foreign Countries (29) the compound of the formula (propamocarb) (XXX) and/or (30) the pyridineamine of the formula (XXXI) (fluazinam) and/or (31) the thiazolecarboxamide of the formula and/or 15 (32) the sulphonamide of the formula Le A 34 16!-Foreign Countries (cyamidazosulfamid) and/or (33) the compound of the formula and/or (34) the compound of the formula (iprodione) 15 and/or (35) the compound of the formula Le A 34 161-Foreign Countries (XXXVI) (procymidone) and/or 5 (36) the diamide of the formula (XXXVH) (thiram) 10 and/or (37) the methoxyacrylate derivative of the formula and/or (38) the quinoline derivative of the formula Le A 34 16!-Foreign Countries (XXXIX) (quinoxyfen) and/or 5 (39) the phenylamide derivative of the formula (XXXX) (oxadixyl) 10 and/or (40) the phenylamide derivative of the formula (XXXXI) and/or (benalaxyl) (41) the dicarboxime derivative of the formula Le A 34 161-Foreign Countries and/or (42) the phosphonic acid of the formula H—Ij’—OH OH , (XXXXHa) (captan) (ΧΧΧΧΠΙ) (phosphonic acid) and/or (43) the pyrrole derivative of the formula and/or (XXXXIV) (fludioxonil) (44) the phenyl carbonate of the formula Le A 34 16!-Foreign Countries (XXXXV) and/or (diethofencarb) 5 (45) the copper compounds a) copper oxychloride (XXXXVIa) b) copper hydroxid (XXXXVIb) 10 and/or (46) the imidazole derivative of the formula Cl (ΧΧΧΧΥΠ) (prochloraz) and/or Le A 34 161-Foreign Countries (47) the triazole derivative of the formula (difenconazole) 5 and/or (xxxxvmb) (hexaconazole) and/or (XXXXVme) (cyproconazole) and/or Le A 34 161-Foreign Countries d) and/or e) and/or (XXXXVDIf) (myclobutanil) Le A 34 161-Foreign Countries and/or g) and/or h) .cf 2 —chf 2 0 (XXXXVfflg) (fenbuconazole) (XXXXVmh) (tetraconazole) and/or 15 (48) a compound of the general formula R OCH, N-u OCH״ □ OCH״ «3 (XXXXIX) Le A 34 161-Foreign Countries in which R 1 represents unsubstituted or fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl, and/or (49) N-methyl-2-(methoxyimino)-2-[2-([ l-(3-tri-fluoro-methylphenyl)ethoxy]iminomethyl)phenyl]acetamide of the formula (XXXXX) and/or (50) 2,4-dihydro-5-methoxy-2-methyl-4-[2-([([l-(3-tri-fluoromethylphenyl)ethylidene]amino)oxy]methyl)phenyl]-3H-l,2,4-triazol3-one of the formula and/or Le A 34 161-Foreign Countries (51) the compound of the formula (XXXXXII)
- 2Active compound combinations according to Claim 1, comprising at least one compound of the formula (I) as defined in Claim 1 and (3) an aniline derivative of the formula HC N C ^SO-N(CH 3 ) 2 (IVb) and/or (5) the zinc propylene-l,2-bis-(dithiocarbamidate) of the formula —[Zn-S—C—NH-CH—CH—NH—C-S](VI) (propineb) and/or Le A 34 161-Foreign Countries (6) at least one thiocarbamate of the formula (Vile) Me = mixture of Zn and Mn and/or (7) the aniline derivative of the formula (VIII) and/or (8) the compound of the formula O <j;H(CH 3 ) 2 _ (CH 3 ) 2 CH-O-C—NH—CH-C—NH—CH—CH 3 (|X) O CH 3 (iprovalicarb) and/or Le A 34 161-Foreign Countries (11) the compound of the formula and/or (12) the compound of the formula (trifloxystrobin) (XIII) 10 and/or (13) the compound of the formula 45״. and/or (X1V) Le A 34 161-Foreign Countries (18) the phthalimide derivative of the formula Q (XIX) (20) the hydroxyethyl-triazole derivative of the formula (XXI) and/or (26) the halogeno-benzimidazole of the formula (XXVII) CH״ <3 and/or Le A 34 161-Foreign Countries (27) the halogenopyrimidine of the formula (-XXVIII) (28) the tetrachloro-isophthalo-dinitrile of the formula (XXIX) (chlorothalonil) and/or (30) the pyridinamine of the formula Cl (fluazinam) (XXXI) and/or Le A 34 161-Foreign Countries (45) the copper compounds a) copper oxychloride b) copper hydroxide (XXXXVIa) (XXXXVIb).
- 3Composition according to Claim 1, characterized in that in the active compound combinations the weight ratio of active compound of the formula (I) to - active compound of group (1) is from 1:0.1 to 1:50, - active compound of group (2) is from 1:0.1 to 1:50, - active compound of group (3) is from 1:1 to 1:150, - active compound of group (4) is from 1:0.1 to 1:10, - active compound of group (5) is from 1:1 to 1:150, - active compound of group (6) is from 1:1 to 1:150, - active compound of group (7) is from 1:0.1 to 1:50, - active compound of group (8) is from 1:0.1 to 1:50, - active compound of group (9) is from 1:0.02 to 1:50, - active compound of group (10) is from 1:0.1 to 1:50, - active compound of group (11) is from 1:0.1 to 1:50, - active compound of group (12) is from 1:0.1 to 1:50, - active compound of group (13) is from 1:0.1 to 1:50, - active compound of group (14) is from 1:0.1 to 1:50, - active compound of group (15) is from 1:0.2 to 1:50, - active compound of group (16) is from 1:0.1 to 1:50, - active compound of group (17) is from 1:0.1 to 1:50, - active compound of group (18) is from 1:1 to 1:150, - active compound of group (19) is from 1:0.1 to 1:150, - active compound of group (20) is from 1:0.02 to 1:50, - active compound of group (21) is from 1:0.05 to 1:20, - active compound of group (22) is from 1:0.1 to 1:50, - active compound of group (23) is from 1:0.1 to 1:50, - active compound of group (24) is from 1:0.01 to 1:50, - active compound of group (25) is from 1:0.1 to 1:50, - active compound of group (26) is from 1:0.1 to 1:50, - active compound of group (27) is from 1:0.1 to 1:50, 5 - active compound of group (28) is from 1:1 to 1:150, '. - active compound of group (29) is from 1:1 to 1:150, - active compound of group (30) is from 1:0.1 to 1:50, - active compound of group (31) is from 1:0.1 to 1:50, - acti ve compound of group (32) is from 1:0.1 to 1:50, !0 - active compound of group (33) is from 1:0.1 to 1:50, - active compound of group (34) is from 1:0.1 to 1:50, - active compound of group (35) is from 1: 0.1 to 1:50, :. - active compound of group (36) is from 1:1 to 1:150, - active compound of group (37) is from 1:0.1 to 1:50, 15 י’ - active compound of group (38) is from 1:0.1 to 1:50, r - active compound of group (39) is from 1:0.1 to 1:50, - active .compound of group (40) is from 1:0.1 to 1:50, ־ active compound of group41) ׳) is from 1:1 to 1:150, - active compound of group (42) is from 1:1 to 1:150, 20 - active compound of group (43) is from 1:0.1 to 1:50, - active compound of group (44) is from 1:0.1 to 1:50, - acti ve compound of group (45a) is־ from 1:1 to 1:150, - active compound of group (45b) is from 1:1 to 1:150, - active compound of group (46) is from 1:0.1 to 1:50, _ 25 - active compound of group (47a) is from 1:0.1 to 1:50, - active compound of group (47b) is from 1:0,1 to 1:50, - active compound of group (47c) is from 1:0.1 to 1:50, - active compound of group (47d) is from 1:0.1 to 1:50, - active compound of group (47e) is from 1:0.1 to 1:50, 30 - active compound of group (47f) is from 1:0.1 to 1:50, - active compound of group (47g) is from 1:0.1 to 1:50, Le A 34 16!-Foreign Countries - active compound of group (47h) is from 1:0.1 to 1:50, - active compound of group (48) is from 1:0.1 to1:50, - active, compound of group (49) is from 1:0.1 to1:50, - active compound of group (50) is from 1:0.1 to1:50, 5 - active compound of group (51) is from 1:0.1 to 1:50.
Independent claims6
560 paragraphs in 6 sections, as filed
Fungicidal active compound combinations
The present invention relates to novel active compound combinations which consist of a known fluoro-benzothiazole derivative and further known fungicidally active compounds, and which are highly suitable for controlling phytopathogenic fungi.
It is already known that isopropyl l־({[l-(6־fluoro-l,3-benzothiazol2־-yl)ethyl]amino }carbonyl)-2-methylpropylcarbamate. has fungicidal properties (cf. EP-A1-775 696). The activity of this compound is good; however, at low application rates it is in some cases not satisfactory.
Furthermore, it is already known that a large number of triazole derivatives, aniline derivatives, dicarboximides and other heterocycles can be employed for controlling ־ fungi (cf. EP-A 0 040 345, corresponding to IL 75519, DE-A 22 01 063, DE-A 23 24 010, Pesticide Manual, 9<sup>th</sup> Edition (1991), pages 249 and 827, EP-A 0 382 375 and EP-A 0 515 901). Likewise, the activity of these compounds is not always satisfactory at low application rates.
Finally, it is also known that l-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine can be used for controlling animal pests such as insects (cf. Pesticide Manual, 9th Edition (1991), page 491). However, fungicidal properties have hitherto not been described for this compound.
Furthermore, it is already known that 1-(3,5-dimethyl-isoxazol-4-sulphonyl)2־chloro-6,6-difIuoro-[l,3]-dioxolo-[4,5f]-benzimidazole has fungicidal properties (cf. WO 97-06171).
Furthermore, it is already known that substituted azodioxacycloalkenes have fungicidal properties (cf. EP-B-712 396).
Finally, it is also known that substituted halogenopyrimidines have fungicidal properties (cf. DE-A1-196 46 407, EP-B-712 396).
Le A 34 161-Foreign Countries
־2־
It has now been found that the novel active compound combinations comprising a fluorobenzothiazole derivative of the formula
<img file="IL149554A_D0001.tif" />
and (1) a triazole derivative of the formula
<img file="IL149554A_D0002.tif" />
in which
X represents chlorine or phenyl and
Y represents or
<img file="IL149554A_D0003.tif" />
and/or
Le A 34 161-Foreign Countries (2) the triazole derivative of the formula
<img file="IL149554A_D0004.tif" />
and/or (3) an aniline derivative of the formula
<img file="IL149554A_D0005.tif" />
.S---CCLF <sup>N</sup>C (IV),
SO<sub>2</sub>—N(CHA in which
R<sup>1</sup> represents hydrogen or methyl, and/or (4) N-[l4)־-chloro-phenyl)-ethyl]-2,2-dichloro-l-ethyl3־-methyl-cyclopropanecarboxamide of the formula
<img file="IL149554A_D0006.tif" />
<img file="IL149554A_D0007.tif" />
C-H-ChL □ 3 (carpropamid) and/or (V)
Le A 34 161-Foreign Countries (5) the zinc propylene-1,2-bis-(dithiocarbamidate) of the formula
II I Π —[Zn—s—c—NH—CH—CH—NH—C-S]<sub>n</sub>n > = 1 (propineb) and/or (VI) (6) at least one thiocarbamate of the formula
<img file="IL149554A_D0008.tif" />
Me = Zn or Mn or a mixture of Zn and Mn and/or (7) the aniline derivative of the formula
<img file="IL149554A_D0009.tif" />
(fenhexamid) and/or (8) the compound of the formula ft j)H(CH<sub>3</sub>)<sub>2</sub> (CH<sub>3</sub>)<sub>2</sub>CH-O-C-NH-CH-C-NH-CH—^J^-CH<sub>3</sub> (IX) כ Ah<sub>3</sub> (iprovalicarb)
Le A 34 161-Foreign Countries and/or (9) the benzothiadiazole derivative of the formula
<img file="IL149554A_D0010.tif" />
(X) and/or (acibenzolar-S-methyl) (10) the 8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl־l,4-dioxaspiro[5,4]-decane of the formula
<img file="IL149554A_D0011.tif" />
(spiroxamine) and/or (11) the compound of the formula
<img file="IL149554A_D0012.tif" />
and/or
Le A 34 16!-Foreign Countries (12) the compound of the formula
<img file="IL149554A_D0013.tif" />
(trifloxystrobin) (XIII)
HLC u
and/or (13) the compound of the formula
<img file="IL149554A_D0014.tif" />
(XIV) and/or (14) the cyanoxime derivative of the formula ch-ch-nh-c-nh-c-c=noch<sub>3</sub> (XV) (cymoxanil) and/or
Le A 34 161-Foreign Countries (15) a pyrimidine derivative of the formula
NH in which
R<sup>2</sup> represents methyl, —C=C“CH<sub>3</sub> (mepanipyrim) or cyclopropyl (cyprodinyl), and/or (16) an aniline derivative of the formula
CH9 ״<sup>H</sup>3 / *5 I
-CH-COOCH, Z־N< c-ch<sub>2</sub>-o—Cl ch<sub>3</sub> {J (metalaxyl or metalaxyl M) and/or (17) the morpholine derivative of the formula
Q N—C-CH-C (dimetomorph)
OCH״
V
Le A 34 16!-Foreign Countries and/or
<img file="IL149554A_D0015.tif" />
(18) the phthalimide derivative of the formula
<img file="IL149554A_D0016.tif" />
(folpet) (XIX) and/or (19) the phosphorus compound of the formula and/or
Al (fosetyl-AI) (XX) (20) the hydroxyethyl-triazole derivative of the formula
<img file="IL149554A_D0017.tif" />
(XXI) and/or
Le A 34 161-Foreign Countries (21) the l-[(6־chloro-3־pyridinyl)-methyl]-N-nitro-2־imidazolidinimine of the formula
J γ (xxH)
CI^TT N—NO, ״ . . ..
<sup>2</sup> (imidacloprid) and/or . (22) the oxazolidinedione of the formula
CH_ O־°־cy־^ (XXIII)
I N \__) (famoxadon!
and/or (23) the benzamide derivative of the formula
<img file="IL149554A_D0018.tif" />
(zoxamide) (XXIV) and/or
Le A 34 161-Foreign Countries (24) a guanidine derivative of the formula
R<sup>3</sup>
R<sup>3</sup> r—0)—ןןη<sub>2</sub>)<sub>γ</sub>[ν—(ch<sub>2</sub>)j-n-h (xxv) x (2 + ודו) CH<sub>3</sub>COOH in which represents integers from 0 to 5 and
R3 represents hydrogen (17 to 23%) or the radical of the formula =NH nh<sub>2</sub> (77 to 83 %) and/or (25) the triazole derivative of the formula
Cl
<img file="IL149554A_D0019.tif" />
(penconazole) (XXVI) and/or
Le A 34 161-Foreign Countries (26) the halogeno-benzimidazole of the formula
<img file="IL149554A_D0020.tif" />
(XXVII) and/or (27) the halogenopyrimidine of the formula
<img file="IL149554A_D0021.tif" />
(XXVIII) (28) the tetrachloro-isophthalo-dinitrile of the formula
<img file="IL149554A_D0022.tif" />
(XXIX) (chlorothalonil) and/or
Le A 34 161-Foreign Countries (29) the compound of the formula
<img file="IL149554A_D0023.tif" />
(XXX) (propamocarb) and/or (30) the pyridineamine of the formula
<img file="IL149554A_D0024.tif" />
(XXXI) (fluazinam) and/or (31) the thiazolecarboxamide of the formula
<img file="IL149554A_D0025.tif" />
(ethaboxam) and/or (32) the sulphonamide of the formula
Le A 34 16 !-Foreign Countries
<img file="IL149554A_D0026.tif" />
and/or (33) the compound of the formula
Me
Me
<img file="IL149554A_D0027.tif" />
(XXXIV) and/or (34) the compound of the formula
<img file="IL149554A_D0028.tif" />
(iprodione) and/or (35) the compound of the formula
Le A 34 161-Foreign Countries and/or
<img file="IL149554A_D0029.tif" />
Cl (36) the diamide of the formula
<img file="IL149554A_D0030.tif" />
(XXXVI) (procymidone) (ΧΧΧΥΠ) (thiram) and/or (37) the methoxyacrylate derivative of the formula and/or
<img file="IL149554A_D0031.tif" />
(xxxvm) (picoxystrobin) (38) the quinoline derivative of the formula
Le A 34 161-F0rei2n Countries and/or
<img file="IL149554A_D0032.tif" />
(39) the phenylamide derivative of the formula
<img file="IL149554A_D0033.tif" />
(XXXIX) (quinoxyfen) (XXXX) (oxadixyl) and/or (40) the phenylamide derivative of the formula and/or
<img file="IL149554A_D0034.tif" />
(XXXXI) (benalaxyl) (41) the dicarboxime derivative of the formula
Le A 34 161-Foreign Countries
<img file="IL149554A_D0035.tif" />
(XXXXDa) (captan) and/or (42) the phpsphonic acid of the formula
Η—P—OH
OH (ΧΧΧΧΙΠ) (phosphonic acid) and/or (43) the pyrrole derivative of the formula
<img file="IL149554A_D0036.tif" />
(XXXXIV) (fludioxonil) and/or (44) the phenyl carbonate of the formula
Le A 34 161-Foreign Countries
<img file="IL149554A_D0037.tif" />
(XXXXV) (diethofencarb) and/or (45) the copper compounds
a) copper oxychloride
b) copper hydroxid (XXXXVIa) (XXXXVIb) and/or (46) the imidazole derivative of the formula
<img file="IL149554A_D0038.tif" />
(prochloraz) and/or
Le A 34 16!-Foreign Countries (47) the triazole derivative of the formula a)
<img file="IL149554A_D0039.tif" />
(difenconazole) and/or
b) and/or and/or
d)
<img file="IL149554A_D0040.tif" />
<img file="IL149554A_D0041.tif" />
(XXXXVmb) (hexaconazole) (XXXXVme) (cyproconazole)
Le A 34 161-Foreign Countries and/or
e) and/or and/or
<img file="IL149554A_D0042.tif" />
<img file="IL149554A_D0043.tif" />
<img file="IL149554A_D0044.tif" />
(xxxxvmd) (flusilazole) (XXXXVIlle) (propiconazole) (XXXXVmf) (myclobutanil)
Le A 34 16!-Foreign Countries
<img file="IL149554A_D0045.tif" />
(fenbuconazole) and/or
h) .CF—CHF<sub>2 </sub>0
J| I \ _] (xxxxvmh) (tetraconazole) and/or (48) a compound of the general formula
<img file="IL149554A_D0046.tif" />
och<sub>3</sub>
N<sub>v </sub>OCH, □
OCH<sub>3</sub> (XXXXIX) in which
Le A 34 16!-Foreign Countries
R<sup>1</sup> represents unsubstituted or fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl, and/or (49) N-methyl-2-(methoxyimino)-2-[2-([l-(3-tri-fluoro-methylphenyl)ethoxy]iminomethyl)phenyl]acetamide of the formula
<img file="IL149554A_D0047.tif" />
(XXXXX) and/or (50) 2,4-dihydro-5-methoxy-2-methyl-4-[2-([([l-(3-tri-fluoro- methylphenyl)ethylidene]amino)oxy]methyl)phenyl]-3H-l,2,4-triazol-3-one of the formula
<img file="IL149554A_D0048.tif" />
and/or (51) the compound of the formula
Le A 34 16!-Foreign Countries
<img file="IL149554A_D0049.tif" />
(XXXXXII) have very good fungicidal properties.
Surprisingly, the fungicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the activities of the individual active compounds. Thus, an unforeseeable, true synergistic effect is present, and not just an addition of activities.
From the structural formula of the active compound of the formula (I), it can be seen that the compound has two asymmetrically substituted carbon atoms. Accordingly, the product can be present as a mixture of different isomers or else in the form of a single isomer.
Preferred compounds of the formula (I) are compounds in which the amino acid moiety is formed from i-propyloxycarbonyl-L-valine and the fluorobenzothiazoleethylamine moiety is racemic, but has, in particular, the (R) configuration.
The formula (Π) includes the compounds l-(4-chloro-phenoxy)-3,3-dimethyl-l־(l,2,4-triazol-l-yl)-butan-2-one of the formula
Le A 34 161-Foreign Countries
<img file="IL149554A_D0050.tif" />
(Ha) l-(4-chloro-phenoxy)-3,3-dimethyl־l-(l,2,4־triazol-l-yl)-butan-2-ol of the formula
<img file="IL149554A_D0051.tif" />
(Hb) and l4)־-phenyl-phenoxy)-3,3־dimethyl-l-(l,2,4־triazol-l-yl)-butan-2-ol of the formula
<img file="IL149554A_D0052.tif" />
The formula (IV) includes the aniline derivatives of the formulae —cci<sub>2</sub>f
Nf (IVa)
SO2־N(CH<sub>3</sub>)<sub>2</sub> (dichlofluanid)
<img file="IL149554A_D0053.tif" />
and
Le A 34 161-Foreign Countries
<img file="IL149554A_D0054.tif" />
<sup>N</sup>C
SO-N(CH<sub>3</sub>)<sub>2</sub> (IVb) (tolylfluanid)
It is evident from the structural formula for the active compound of the formula (V) that the compound has three asymmetrically substituted carbon atoms. The product 5 may therefore be present as a mixture of different isomers, or else in the form of a single component. Particular preference is given to the compounds
N-(R)-[l-(4-chloro-phenyl)-ethyl]-(lS)-2,2-dichloro-l-ethyl-3t-methyMR-cyclopropanecarboxamide of the formula
<img file="IL149554A_D0055.tif" />
arid
N-(R)-[l-(4-chloro-phenyl)-ethyl]-(lR)-2,2-dichloro-l-ethyl-3t-methyl-lR-cyclopropanecarboxamide of the formula
<img file="IL149554A_D0056.tif" />
The formula (VII) includes the compounds (Vila) Me = Zn (zineb),
Le A 34 161-Foreign Countries (Vllb) Me = Mn (maneb) and (Vile) mixture of (Vila) and (VHb) (mancozeb).
The formula (XVI) includes the compounds
<td> (XVIa)</td><td> R<sup>2</sup> = CH<sub>3</sub></td><td> (pyrimethanil) and</td>
<td> (XVIb)</td><td> r<sup>2</sup>-X]</td><td> (cyprodinyl)</td>
<td> (XVIc)</td><td> r2 = -OC-CH<sub>3</sub></td><td> (mepanipyrim)</td>
<td colspan="2"> The compound of the formula</td><td> (XVII) can be present as methyl N-(2,6-</td>
dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate (metalaxyl, XVIIa) or as methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate(metalaxyl-M, XVIIb).
The hydroxyethyl-triazole derivative of the formula (XXI) can be present in the “thiono” form of the formula
<img file="IL149554A_D0057.tif" />
<img file="IL149554A_D0058.tif" />
or in the tautomeric “mercapto” form of the formula
<img file="IL149554A_D0059.tif" />
(XXI'b)
For simplicity's sake, only the “thiono” form is given in each case.
Le A 34 161-Foreign Countries
The guanidine derivative of the formula (XXV) is a substance mixture with the common name guazatine.
From the structural formula for the active compouds of the formula (XXXXIX), it can be seen that the compounds can be present as E or Z isomers. Accordingly, the product can be present as a mixture of different isomers or else in the form of a single isomer. Preference is given to compounds of the formula (XXXXIX) in which the compounds of the formula (XXXXIX) are present as E isomer. Particular preference is given to the compounds of the formulae
OCH<sub>3</sub> (XXXXIXa)
N-h OCH, w and
N-m OCH, w and
OCH<sub>3</sub> (xxxxixc)
Le A 34 161-Foreign Countries ־ 27 and
<img file="IL149554A_D0060.tif" />
and
<img file="IL149554A_D0061.tif" />
and
<img file="IL149554A_D0062.tif" />
(XXXXIXf) and their isomers.
The following active compounds are particularly preferred mixing partners of the compounds of the formula (I):
(3) tolylfluanid (IVb), (5) propineb (VI), (6) mancozeb (Vile), (7) fenhexamid (VIII),
Le A 34 161-Foreign Countries (8) iprovalicarb (IX), (11) azoxystrobin (ΧΠ), (12) trifloxystrobin (ΧΙΠ), (13) compound of the formula (XTV), (18) folpet (XIX־), (20)׳ compound of the formula (XXI), (26) compound of the formula (XXVH), (27) compound of the formula (XXVHI), (28) chlorothalonil (XXIX), (30) fluazinam (XXXI), and (45) copper compounds
a) copper oxychloride (XXXXVIa)
b) copper hydroxide (XXXXVIb).
The components which are present in the active combinations according to the invention in addition to a halogeno-benzimidazole of the formula (XXVII) are also known.
Specifically, the active compounds are described in the following publications:
(1) compounds of the formula (H)
DE-A 22 01 063
DE-A 23 24 010 (2) compound of the formula (HI)
EP-A 0 040 345 (3) compounds of the formula (IV)
Pesticide Manual, 9th Ed. (1991), pages 249 and 827 (4) compound of the formula (V) and individual derivatives thereof
Le A 34 161-Foreign Countries
EP-A 0 341 475 (5) compound of the formula (VI)
Pesticide Manual, 9th Ed. (1991), page 726 (6) compounds of the formula (VII)
Pesticide Manual, 9th Ed. (1991), pages 529,531 and 866 (7) compound of the formula (VIH)
EP-A 0 339 418 (8) compound of the formula (IX)
EP-A 0472 996 (9) compound of the formula (X)
EP-A 0 313 512 (10) compound of the formula (XI)
EP-A 0 281 842 (11) compound of the formula (ΧΠ)
EP-A 0 382 375 (12) compound of the formula (XIH)
EP-A-460 575 (13) compound of the formula (XIV)
DE-A 19602 095 (14) compound of the formula (XV)
Pesticide Manual, 9th Ed. (1991), page 206
Le A 34 161-Foreign Countries
־30־ (15) compounds of the formula (XVI)
EP-A0 270 111
EP-A 0 310 550 (16) compound of the formula (XVII)
Pesticide Manual, 9th Ed. (1991),' page 554 (17) compound of the formula (XV1H)
EP-A 0 219 756 (18) compound of the formula (XIX)
Pesticide Manual, 9th Ed. (1991), page 431 (19) compound of the formula (XX)
Pesticide Manual, 9th Ed. (1991), page 443 (20) compound of the formula (XXI)
WO 96-16048 (21) compound of the formula (ΧΧΠ)
Pesticide Manual, 9th Ed. (1991), page 491 (22) compound of the formula (ΧΧΙΠ)
EP-A 0 393 911 (23) compound of the formula (XXTV)
EP-A 0 600 629 (24) substance of the formula (XXV)
Pesticide Manual, 9th Ed. (1991), page 461
Le A 34 16!-Foreign Countries (25) compound of the formula (XXVI) Pesticide Manual, 9th Ed. (1991), page 654 (26) compound of the formula (XXVII)
WO 97-06171 (27) compound of the formula (XXVIII)
DE-A1-196 46 407, EP-B-0 712 396 (28) compound of the formula (XXIX)
US 3 290 353 (29) compound of the formula (XXX)
DE-A-1567169 (30) compound of the formula (XXXI)
EP-A-0 031 257 (31) compound of the formula (XXXH)
EP-A-0 639 547 (32) compound of the formula (XXXIH)
EP-A-0 298 196 (33) compound of the formula (XXXIV)
EP-A-600629 (34) compound of the formula (XXXV)
DE-A-2149 923
Le A 34 161-Foreign Countries (35) compound of the formula (XXXVI)
DE-A-2 012 656 (36) compound of the formula (XXXVII)
US 1 972 961 (37) compound of the formula (XXXVIII)
EP-A-326 330 (38) compound of the formula (XXXIX)
EP-A 278 595 (39) compound of the formula (XXXX)
DE-A-3 030026 (40) compound of the formula (XXXXI)
DE-A-2 903 612 (41) compound of the formula (ΧΧΧΧΠ)
US-2 553 770 (42) compound of the formula (ΧΧΧΧΙΠ) known and commercially available (43) compound of the formula (XXXXIV)
EP-A-206 999 (44) compound of the formula (XXXXV)
EP-A-78 663 (45) a) compound of the formula (XXXXVIa)
Le A 34 161-Foreign Countries known and commercially available
b) compound of the formula (XXXXVIb) known and commercially available (46) compound of the formula (XXXXVII)
DE-A-2429 523 (47) a) compound of the formula (XXXXVIHa)
ΕΡ-Α-1Ί2284
b) compound of the formula (XXXXVDIb) DE-A-3 042 303
c) compound of the formula (XXXXVIUc) DE-A-3 406 993
d) compound of the formula (XXXXVIIId) EP-A-68 813
e) compound of the formula (XXXXVDIe) DE-A-2551560
f) compound of the formula (XXXXVDIf) EP-A-145 294
g) compound of the formula (XXXXVIHg) DE-A-3 721 786
h) compound of the formula (XXXXVIIIh)
EP-A-234 242
Le A 34 161-Foreign Countries (48) compound of the formula (XXXXIX)
WO 96/23763 (49) compound of the formula (XXXXX)
EP-A-596 254 (50) compound of the formula (XXXXXI)
WO 98/23155 (50) compound of the formula (ΧΧΧΧΧΠ)
EP-A-569 384.
In addition to an active compound, of the formula (I), the active compound combinations according to the invention comprise at least one active compound of the compounds of groups (1) to (51). Additionally, they may comprise further fungicidally active additives.
The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general, from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (1), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (2), from 1 to 150 parts by weight, preferably from 1 to 100 parts by weight, of active compound of group (3),
Le A 34 161-Foreign Countries from 0.1 to lOparts by weight, preferably from 0.2 to 5 parts by weight, of active compound of group (4), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (5), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (6), from 0.1 to 50 parts by weight, preferably from 1 to 20 parts by weight, of active compound of group (7), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (8), from 0.02 to 50 parts by weight, preferably from 0.1 to 10 parts by weight, of active compound of group (9), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (10), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (11), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (12), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (13),
Le A 34 16!-Foreign Countries from 0,1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (14), from 0.2 to 50 parts by weight, preferably from 1 to 20 parts by weight, of active compound of group (15), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (16), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (17), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (18), from 0.1 to 150 parts by weight, preferably from 1 to 100 parts by weight, of active compound of group (19), from 0.02 to 50 parts by weight, preferably from 0.2 to 10 parts by weight, of active compound of group (20), from 0.05 to 20 parts by weight, preferably from 0.1 to 10 parts by weight, of active compound of group (21), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (22), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (23),
Le A 34 161-Foreign Countries from 0,01 to 150 parts by weight, preferably from 1 to 100 parts by weight, of active compound of group (24), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (25), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (26), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (27), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (28), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (29), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (30), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (31), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (32), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (33),
Le A 34 161-Foreign Countries from 0.1 to 50 parts by weight, preferably 1 to 20 parts by weight, of active compound of group (34), from 0.1 to 50 parts by weight, preferably from 1 to 10 parts by weight, of active compound of group (35), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (36), from 0.1 to 50 parts by weight, preferably from 0,2 to 20 parts by weight, of active compound of group (37).
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (38), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (39), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (40), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (41), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (42), from 0.1 to 50 parts by weight, preferably from 1 to 20 parts by weight, of active compound of group (43),
Le A 34 161-Foreign Countries from 0.1 to 50 parts by weight, preferably from 1 to 20 parts by weight, of active compound of group (44), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (45a), from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (45b), from 0.1 to 50 parts by weight, preferably from 0,2 to 20 parts by weight, of active compound of group (46), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active, compound of group (47a), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47b), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47c), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47d), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47e), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47f),
Le A 34 161-Foreign Countries from 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of group (47g), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47h), from 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of group (48), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (49), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (50), from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (51) are present per part by weight of active compound of the formula (I).
The active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
The active compound combinations according to the invention are particularly suitable for controlling Phytophthora infestans and Plasmopara viticola.
The fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of aboveground parts of plants, of propagation stock and seeds, and of the soil. The active
Le A 34 161-Foreign Countries compound combinations according to the invention can be employed for foliar application or else as seed dressings. .
The active compound combinations according to the invention may also be employed to increase the yield of crops. However, they have reduced toxicity and are tolerated well by plants.
According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant cultivars which can or cannot be protected by plant breeders certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.
The treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by action on their environment, habitat or storage, area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multilayer coating.
The active compound combinations according to the invention can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders,
Le A 34 161-Foreign Countries foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
These formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents include: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Lx A 34 161-Foreign Countries
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%.
The active compound combinations according to the invention, as such or in their formulations, can also be applied in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, to broaden the activity spectrum or to prevent the development of resistance, for example. In many cases, synergistic effects are obtained, i.e. the activity of the mixture is greater than the activity of the individual components.
A mixture with other known active compounds such as herbicides or with fertilizers and growth regulators is also possible.
The active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting.
Le A 34 161-Foreign Countries
When using the active compound combinations according to the invention, the application rates can be varied within a relatively wide range, depending on the kind of application. In the treatment of parts of plants, the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In the treatment of seeds, the application rates of the active compound combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.
The good fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds the sum of individual activities.
A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
The expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S.R., Calculating Synergistic and Antagonistic Responses of Herbicide Combinations, Weeds 15, (1967), 20-22):
If
X is the efficacy when applying active compound A at an application rate of mg/ha,
Y is the efficacy when applying active compound B at an application rate of n g/ha and
Le A 34 161-Foreign Countries
E is the efficacy when applying the active compounds A and B at an application rate of m and n g/ha, then
The efficacy is calculated in %. 0% is an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.
The examples that follow illustrate the invention. However, the invention is not limited to the examples.
Le A 34 161-Foreign Countries
Example 1
Phytophthora test (tomato) / protective
Solvent: 47 parts by weight of acetone
Emulsifier: 3 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabin at about 20°C and 100% relative atmospheric humidity.
Evaluation is carried out 3 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
The activity found for the active compound combination according to the invention is greater than the calculated activity, i.e. there is a synergistic effect. At a mixing ratio of 1:1 and an application rate of 0.1 g/ha, the combination of the compound of the formula (I) and the halogeno-benzimidazole of the formula No. XXVII has an actual efficacy of 73%. At 63%, the expected value, calculated using Colby's formula, is considerably lower.
Active compounds, application rates and test results are shown in the tables below.
Le A 34 161-Foreign Countries
Table
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (XXVII) <sub>F</sub>x XX )־<sup>c1</sup> H,C \^O °x J <sup>0</sup><sup>n</sup>A<sub>3</sub>״</td><td> 0.1</td><td> 30</td>
<td> compound of the formula (I) H<sub>3</sub>C. .CH<sub>3</sub> XX-p 0 CH,</td><td> 0.1</td><td> 47</td>
Mixture according to the invention:
<td> Active compound</td><td> Mixing ratio</td><td> Active compound application rate in g/ha</td><td> Actual efficacy</td><td> Expected value, calculated using Colby's formula</td>
<td> XXVII</td><td> 1..</td><td> 0.1</td><td><sub>ג7</sub> ץ</td><td> 63</td>
Le A 34 161-Foreign Countries
Table 2
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) H<sub>3</sub>C״CH<sub>3 c</sub> CH״ Ο<sup>3</sup> Y <sup>3</sup> ΖΛ-F Λ Λ AJUAY H.C O N * γ Y S <sup>3</sup> h II 1 o CH<sub>3</sub></td><td> 1</td><td> 47</td>
<td> propineb (VI) 8 ?<sup>H3</sup> ״ —[Zn—S—C—NH—CHs—CH—NH—C—S]— 2 J״ (v|) n > = 1 (propineb)</td><td> 20</td><td> 19</td>
<td> Mixture according to the invention Mixing ratio</td><td> Active Actual Expected value compound efficacy calculated using application Colby's formula rate in g/ha</td>
<td><sup>(I)</sup> 1 <sub>+</sub> > 120־ propineb (VI) ׳</td><td> t } <sup>94 57</sup> 20</td>
Le A 34 161-Foreign Countries
Table 3 Phytophthora test (tomato) / protective
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) H,C. >CH, V<sup>=</sup>\—c TiX JlX H״C O N * Y y S <sup>3</sup> h II 1 0 CH,</td><td> 1</td><td> 47</td>
<td> chlorothalonil (XXIX) CN Cl^y^XN ...</td><td> 20</td><td> 12</td>
<td> Mixture according to the invention</td><td></td><td></td><td></td>
<td> Mixing ratio</td><td> Active</td><td> Actual</td><td> Expected value</td>
<td></td><td> compound</td><td> efficacy</td><td> calculated using</td>
<td></td><td> application</td><td></td><td> Colby's formula</td>
<td></td><td> rate in g/ha</td><td></td><td></td>
chlorothalonil (XXIX) J <sup>li20</sup>
Le A 34 161-Foreign Countries
Table 4
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td rowspan="2"> Active compound application rate in g/ha</td><td rowspan="2"> Efficacy in %</td>
<td></td>
<td> compound of the formula (I) CH<sub>3</sub> O<sup>3C</sup>Y<sup>CH3</sup> Ν'Χ<sup>-</sup> 0 ch<sub>3</sub></td><td> 1</td><td> 47</td>
<td> dichlofluanid (IVa) ✓θ—CCLF \ /־־<sup>N</sup>\ ^SO<sub>2</sub>-N(CH<sub>3</sub>)<sub>2</sub></td><td> 20</td><td> 5</td>
<td> Mixture according to the invention:</td><td></td><td></td><td></td>
<td> Mixing ratio</td><td> Active</td><td> Actual</td><td> Expected value</td>
<td></td><td> compound</td><td> efficacy</td><td> calculated using</td>
<td></td><td> application</td><td></td><td> Colby's formula</td>
<td></td><td> rate in g/ha</td><td></td><td></td>
1:20 dichlofluanid (iva)
Le A 34 161-Foreign Countries
Table 5
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td rowspan="2"> Active compound application rate in g/ha</td><td rowspan="2"> Efficacy in %</td>
<td> -</td>
<td> compound of the formula (I) H,C. .CH״ c CH״ Ο<sup>3</sup> Y <sup>3</sup> N0\ /)—<sup>F</sup> AAJUuy H״C 0 N * V γ S <sup>3</sup> h II 1 0 CH״ o</td><td> 1</td><td> 47</td>
<td> tolylfluanid (IVb) —CCLF <sup>H</sup>3<sup>C</sup> \ / \=/ ^SO-N(CH<sub>3</sub>)<sub>2</sub></td><td> 20</td><td> 21</td>
<td> Mixture according to the invention: Mixing ratio</td><td> Active Actual Expected value compound efficacy calculated using application Colby's formula rate in g/ha</td>
<td> . ו id 20־! J <sub>+</sub></td><td> 1 1 <sub>+</sub> f <sup>95 58</sup></td>
<td> tolylfluanid (IVa)</td><td> 20</td>
Le A 34 161-Foreign Countries
Table 6
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) r fV«. <sup>0</sup> Η Ί 1 <sup>s </sup>o CH, □</td><td> 1</td><td> 47</td>
<td> folpet (XIX) 0 V /<sup>n</sup>—<sup>s</sup> U CCL 0</td><td> 20</td><td> 0</td>
<td> Mixture according to the invention:</td><td></td><td></td><td></td>
<td> Mixing ratio</td><td> Active</td><td> Actual</td><td> Expected value</td>
<td></td><td> compound</td><td> efficacy</td><td> calculated using</td>
<td></td><td> application</td><td></td><td> Colby's formula</td>
<td></td><td> rate in g/ha</td><td></td><td></td>
<td> (I)</td><td> I <sup>1</sup> I</td>
<td></td><td> Γ 1:20 f 95 47</td>
<td> +</td><td> J <sup>+</sup> J</td>
<td> folpet (XIX)</td><td> 20</td>
Le A 34 161-Foreign Countries
Table?
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) H,C. ,CH, CH״ Ο<sup>3</sup> Y <sup>3</sup> N״\\ //~<sup>F</sup> IaJUY H״C 0 N*Y T S <sup>3</sup> h II 1 0 CH, □</td><td> 1</td><td> 39</td>
<td> mancozeb (Vile)</td><td> 20</td><td> 28</td>
<td colspan="2"> Mixture according to the invention:</td><td rowspan="2"> Active compound application rate in g/ha</td><td rowspan="2"> Actual efficacy</td><td rowspan="2"> Expected value calculated using Colby's formula</td>
<td></td><td> Mixing ratio</td>
<td> (I)</td><td></td><td> 1</td><td> ר</td><td></td>
<td> +</td><td> 1:20</td><td> +</td><td> f 68</td><td> 56</td>
<td> mancozeb (Vile)</td><td></td><td> 20</td><td></td><td></td>
Le A 34 161-Foreign Countries
Table 8
<td> Phytophthora test (tomato) /</td><td> protective</td><td></td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) - H.C. .CH, J<sup>r==</sup>\_<sub>f:</sub> CH״ Ο<sup>3</sup> Y <sup>3</sup> //^<sup>F</sup><sup>3</sup> h II 1 o CH, □</td><td> 1</td><td> 47</td>
<td> bitertanol (He)</td><td> 10</td><td> 4</td>
<td> Mixture according to the invention:</td><td></td><td></td><td></td>
<td> Mixing ratio</td><td> Active</td><td> Actual</td><td> Expected value</td>
<td> “ </td><td> compound</td><td> efficacy</td><td> calculated using</td>
<td></td><td> application</td><td></td><td> Colby's formula</td>
<td></td><td> rate in g/ha</td><td></td><td></td>
1:10 bitertanol (lie)
Le A 34 161-Foreign Countries
Table
Phytophthora test (tomato) / protective
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) h״c. /Ch״ CH״ Ο<sup>3</sup> Y <sup>3</sup> nA\ //— F H,C 0 N * γ Y S <sup>3</sup> η II 1 0 CH, J )</td><td> 1</td><td> 47</td>
<td> tebuconazole (TH) _/T\_ <sup>Cl</sup> \ / <sup>CH</sup>2־<sup>CH</sup>29־“<sup>C</sup>(<sup>CH</sup>3)3 Ah<sub>2 </sub>A V N</td><td> 10</td><td> 5</td>
<td colspan="4"> Mixture according to the invention:</td>
<td> Mixing ratio</td><td> Active</td><td> Actual</td><td> Expected value</td>
<td></td><td> compound</td><td> efficacy</td><td> calculated using</td>
<td></td><td> application</td><td></td><td> Colby's formula</td>
<td></td><td> rate in g/ha</td><td></td><td></td>
(I) tebuconazole (III)
1:10 +
50
Le A 34 16!-Foreign Countries
Table
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) H<sub>3</sub>(k .CH״ V<sup>=</sup>\_p CH, o<sup>3</sup> Y <sup>3</sup> νΛ\ # <sup>F </sup>Aww 0 ch<sub>3</sub></td><td> 1</td><td> 47</td>
<td> triadimenol (lib) OH Cl—O-CH-CH—C(CH<sub>3</sub>)<sub>3</sub> A u</td><td> 10</td><td> 0</td>
Mixture according to the invention:
<td> Mixing ratio</td><td> Active Actual Expected value compound efficacy calculated using application Colby's formula rate in g/ha</td>
<td> <!> T <sub>+</sub> J <sup>110־</sup></td><td> ץ <sup>1</sup><sub>+</sub> f 88 47</td>
<td> triadimenol (Hb)</td><td> 10</td>
Le A 34 161-Foreign Countries
Table
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) H<sub>3</sub>C״CH<sub>3</sub> CH, Ο<sup>3</sup> Y <sup>3</sup> NY\ # <sup>F </sup>Υγ 0 ch<sub>3</sub></td><td> 1</td><td> 47</td>
<td> imidacloprid (ΧΧΠ) ״Y Y ClY N—N0<sub>2</sub></td><td> 10</td><td> 0</td>
Mixture according to the invention:
<td> Mixing ratio</td><td> Active , Actual Expected value compound efficacy calculated using application Colby's formula rate in g/ha</td>
<td> ו ו 10־1 J <sub>+</sub></td><td> ן <sup>1</sup> 47 71? <sub>+</sub></td>
<td> imidacloprid (XXII)</td><td> 10</td>
Le A 34 161-Foreign Countries
Table
Phytophthora test (tomato) / protective
<td> Active compound known: — -</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) ch<sub>3</sub> o<sup>3C</sup>Y<sup>CH3</sup> H,C 0 N * γ T S <sup>3</sup> h II 1 0 CH, w</td><td> 1</td><td> 47</td>
<td> compound of the formula (XXI) (20) Cl OH \_/ ־<sup>CH</sup>2 <sup>Cl</sup> (XXI) (j)H<sub>2</sub> ,N. <sub>s</sub> NH</td><td> 10</td><td> 2</td>
<td> Mixture according to the invention:</td><td></td><td></td><td></td>
<td> Mixing ratio</td><td> Active</td><td> Actual</td><td> Expected value</td>
<td></td><td> compound</td><td> efficacy</td><td> calculated using</td>
<td></td><td> application</td><td></td><td> Colby's formula</td>
<td></td><td> rate in g/ha</td><td></td><td></td>
J48 62 ־ (XXI) (20)
Le A 34 161-Foreign Countries
Table Phytophthora test (tomato) / protective
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) - : H<sub>q</sub>c. .ch״ CH״ Ο<sup>3</sup> Y <sup>3</sup> N־Y /Y<sup>F</sup> AwF o CH, w</td><td> 1</td><td> 47</td>
<td> fenhexamid (VDI) OJ1 _/ץ C-NH-C ר—OH CH״ /\ <sup>3</sup> Cl Cl</td><td> 10</td><td> 13</td>
<td colspan="2"> Mixture according to the invention:</td><td rowspan="2"> Active compound application rate in g/ha</td><td rowspan="2"> Actual efficacy</td><td rowspan="2"> Expected value calculated using Colby's formula</td>
<td></td><td> Mixing ratio</td>
<td> (I) +</td><td> r 1:10</td><td> 1 +</td><td><sub>70</sub> ץ</td><td> 54</td>
fenhexamid (VIII)
Le A 34 161-Foreign Countries
Table 14
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) H,C. >CH, 7^\_r CH. Ο<sup>3</sup> T <sup>3</sup> N'A o CH, □</td><td> 1</td><td> 47</td>
<td> carpropamid (V) h<sub>3</sub>c K/^CHg Cl--H H״C w</td><td> 10</td><td> 0</td>
<td colspan="2"> Mixture according to the invention:</td><td rowspan="2"> Active compound application rate in g/ha</td><td rowspan="2"> Actual efficacy</td><td rowspan="2"> Expected value calculated using Colby's formula</td>
<td></td><td> Mixing ratio</td>
<td> (I)</td><td> ר</td><td> 1</td><td></td><td></td>
<td> +</td><td> r 1:10</td><td> +</td><td> r 90</td><td> 47</td>
carpropamid (V) 10
Le A 34 161-Foreign Countries
Table 15
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) HA. ,CH, CH, Ο<sup>3</sup> Y <sup>3</sup> NA\ // <sup>F</sup> A A JLUAY ΗΧΟΝ* Y γ S <sup>3</sup> H II 1 0 CH, «3</td><td> 1</td><td> 47</td>
<td> spiroxamine (XI) w-/־y ר C<sub>3</sub>H<sub>7</sub>-n</td><td> 10</td><td> 0</td>
<td> Mixture according to the invention: Mixing ratio</td><td> Active , Actual Expected value compound efficacy calculated using application Colby's formula rate in g/ha</td>
<td><sup>(I)</sup> 1 ♦ > 1.10</td><td> 1־ 1 f 86 47</td>
spiroxamine (XI)
Le A 34 161-Foreign Countries
Table 16
<td> Phytophthora test (tomato) /</td><td> protective</td><td></td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) H<sub>3</sub>C<sub>X/</sub>GH<sub>3 </sub>CH, O<sup>3 3</sup> # <sup>f</sup> 0 ch<sub>3</sub> ני</td><td> 1</td><td> 39</td>
<td> fluazinam (XXXI) Cl cf<sub>3</sub>-A y—HAk/<sup>c| </sup>IJ CLN^^'^CF, c. «נ</td><td> 10</td><td> 56</td>
<td> Mixture according to the invention: Mixing ratio</td><td> Active compound application rate in g/ha</td><td> Actual efficacy</td><td> Expected value calculated using Colby's formula</td>
<td><sup>(I)</sup> Λ</td><td> 1</td><td> ר</td><td></td>
<td> r <sup>1:10</sup></td><td></td><td> r 87</td><td> 73</td>
<td><sup>+</sup> J</td><td> +</td><td> J</td><td></td>
<td> fluazinam (XXXI)</td><td> 10</td><td></td><td></td>
Le A 34 161-Foreign Countries
Table 17
<td> Phytophthora test (tomato) /</td><td colspan="2"> protective</td>
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) H<sub>3</sub>C״CH<sub>3 </sub>CH, 0<sup>3</sup> Y <sup>3</sup> νΛ\ # <sup>f </sup>Λ A LuP H,C O N * Y T S <sup>3</sup> H II 1 0 CH״ u</td><td> 1</td><td> 47</td>
<td> compound of the formula (XXVIII)(27) νΎ JU II J I 1 <sup>ch</sup>3 J <sup>H</sup>3<sup>C</sup> Y <sup>Χ</sup>θ<sup>Η</sup>3 *י ־11 0</td><td> 1</td><td> 9</td>
<td colspan="2"> Mixture according to the invention:</td><td rowspan="2"> Active compound application rate in g/ha</td><td rowspan="2"> Actual efficacy</td><td rowspan="2"> Expected value calculated using Colby's formula</td>
<td></td><td> Mixing ratio</td>
<td> (I)</td><td> ו</td><td> 1</td><td> ו</td><td></td>
<td> +</td><td> r 1:1</td><td> +</td><td> r 72</td><td> 52</td>
(XXVIII) (27) 1
Le A 34 16!-Foreign Countries
Table
Phytophthora test (tomato) / protective
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> compound of the formula (I) . CH<sub>3</sub> O<sup>H</sup>3<sup>C</sup>Y<sup>CH3</sup> 41<sup>F</sup><sup>H</sup>3<sup>C 0</sup> H *II 1 <sup>s </sup>0 CH<sub>a</sub> □</td><td> 1</td><td> 47</td>
<td> compound of the formula (XIV) (13) ΟΛΟ) Cl F XL /CL H_C N > 111 גי J ׳N 0</td><td> 1</td><td> 8</td>
<td> Mixture according to the invention:</td><td></td><td></td><td></td>
<td> Mixing ratio</td><td> Active</td><td> Actual</td><td> Expected</td>
<td></td><td> compound</td><td> efficacy</td><td> value</td>
<td></td><td> application</td><td></td><td> calculated</td>
<td></td><td> rate in g/ha</td><td></td><td> using Colby's</td>
formula (I) (XIV)(13)
Le A 34 16!-Foreign Countries
Table 19
Phytophthora test (tomato) / protective
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> formula (I) H,C״CH<sub>3</sub> p MY o CH״ □</td><td> 1</td><td> 56</td>
<td> compound of the formula (XXXXVIa) (40) copper oxychloride</td><td> 50</td><td> 0</td>
Mixture according to the invention:
<td></td><td> Mixing ratio</td><td> Active compound application rate in g/ha</td><td> Actual efficacy</td><td> Expected value calculated using Colby's formula</td>
<td> formula (I) + copper oxychloride</td><td> 1:50</td><td> 1 + 50</td><td> }</td><td> 56</td>
(XXXXVIa)
Le A 34 161-Foreign Countries
Table
<img file="IL149554A_D0063.tif" />
Mixture according to the invention:
<td></td><td> Mixing ratio</td><td> Active compound application rate in g/ha</td><td> Actual efficacy</td><td> Expected value calculated using Colby's formula</td>
<td> formula (I) ־4 azoxystrobin (ΧΠ)</td><td> }</td><td> 1 + 1</td><td> 95</td><td> 80</td>
Le A 34 161-Foreign Countries
Table 21
Phytophthora test (tomato) / protective
<td> Active compound known:</td><td> Active compound application rate in g/ha</td><td> Efficacy in %</td>
<td> formula (I) H״C. ,CH״ /<sup>=</sup>\_<sub>P</sub> CH״ Ο<sup>3</sup> Υ <sup>3</sup> N׳׳Y <sup>F</sup> awY o CH, *9</td><td> 1</td><td> 56</td>
<td> compound of the formula (ΧΙΠ) (12) trifloxystrobin <sup>F</sup> F Ji 0 H״C<sub>X</sub> ,N. Yx > 0׳X) 1 CH״ 0</td><td> 1</td><td> 0</td>
Mixture according to the invention:
Mixing ratio
Active Actual Expected value compound efficacy calculated using application Colby's formula rate in g/ha
Le A 34 161-Foreign Countries formel (I) +
trifloxystrobin (ΧΙΠ)
Contents6
126 sheets
Sheet 1 Sheet 2 Sheet 3 Sheet 4 Sheet 5 Sheet 6 Sheet 7 Sheet 8 Sheet 9 Sheet 10 Sheet 11 Sheet 12 Sheet 13 Sheet 14 Sheet 15 Sheet 16 Sheet 17 Sheet 18 Sheet 19 Sheet 20 Sheet 21 Sheet 22 Sheet 23 Sheet 24 Sheet 25 Sheet 26 Sheet 27 Sheet 28 Sheet 29 Sheet 30 Sheet 31 Sheet 32 Sheet 33 Sheet 34 Sheet 35 Sheet 36 Sheet 37 Sheet 38 Sheet 39 Sheet 40 Sheet 41 Sheet 42 Sheet 43 Sheet 44 Sheet 45 Sheet 46 Sheet 47 Sheet 48 Sheet 49 Sheet 50 Sheet 51 Sheet 52 Sheet 53 Sheet 54 Sheet 55 Sheet 56 Sheet 57 Sheet 58 Sheet 59 Sheet 60 Sheet 61 Sheet 62 Sheet 63 Sheet 64 Sheet 65 Sheet 66 Sheet 67 Sheet 68 Sheet 69 Sheet 70 Sheet 71 Sheet 72 Sheet 73 Sheet 74 Sheet 75 Sheet 76 Sheet 77 Sheet 78 Sheet 79 Sheet 80 Sheet 81 Sheet 82 Sheet 83 Sheet 84 Sheet 85 Sheet 86 Sheet 87 Sheet 88 Sheet 89 Sheet 90 Sheet 91 Sheet 92 Sheet 93 Sheet 94 Sheet 95 Sheet 96 Sheet 97 Sheet 98 Sheet 99 Sheet 100 Sheet 101 Sheet 102 Sheet 103 Sheet 104 Sheet 105 Sheet 106 Sheet 107 Sheet 108 Sheet 109 Sheet 110 Sheet 111 Sheet 112 Sheet 113 Sheet 114 Sheet 115 Sheet 116 Sheet 117 Sheet 118 Sheet 119 Sheet 120 Sheet 121 Sheet 122 Sheet 123 Sheet 124 Sheet 125 Sheet 126
47 members in 26 offices
Priority claims12
| Document | Office | Kind | Date |
|---|---|---|---|
| 19959947 | Germany | A | |
| 19959947 | Germany | A | |
| 10021412 | Germany | A | |
| 10021412 | Germany | A | |
| 0011989 | European Patent Office (EPO) | W | |
| 0011989 | European Patent Office (EPO) | W | |
| 100214126 | – | – | – |
| 199599475 | – | – | – |
| DE1999159947 | – | – | – |
| DE2000121412 | – | – | – |
| PCTEP2000011989 | – | – | – |
| WO2000EP11989 | – | – | – |
Members47
| Document | Office | Kind | |
|---|---|---|---|
| CA2393988A1 | Canada | A1 | |
| DE10021412A1 | Germany | A1 | |
| WO0144215A2 | World Intellectual Property Organization (WIPO) | A2 | |
| AU2164101A | Australia | A | |
| WO0144215A3 | World Intellectual Property Organization (WIPO) | A3 | |
| KR20020059759A | Republic of Korea | A | |
| BR0016336A | Brazil | A | |
| EP1239733A2 | European Patent Office (EPO) | A2 | |
| CZ20022079A3 | Czechia | A3 | |
| IL149554D0 | Israel | D0 | |
| TR200201544T2 | Türkiye | T2 | |
| CO5221089A1 | Colombia | A1 | |
| MXPA02005835A | Mexico | A | |
| HU0203563A2 | Hungary | A2 | |
| HUP0203563A2 | Hungary | A2 | |
| AR026938A1 | Argentina | A1 | |
| HU0203563A3 | Hungary | A3 | |
| HUP0203563A3 | Hungary | A3 | |
| CN1409596A | China | A | |
| ZA200203650B | South Africa | B | |
| JP2003516979A | Japan | A | |
| US2003105146A1 | United States of America | A1 | |
| EP1239733B1 | European Patent Office (EPO) | B1 | |
| AT243933T | Austria | T | |
| ATE243933T1 | Austria | T1 | |
| DE50002776D1 | Germany | D1 | |
| US6624183B2 | United States of America | B2 | |
| DK1239733T3 | Denmark | T3 | |
| NZ519460A | New Zealand | A | |
| PT1239733E | Portugal | E | |
| ES2197124T3 | Spain | T3 | |
| RU2002119003A | Russian Federation | A | |
| US2004029840A1 | United States of America | A1 | |
| PL355756A1 | Poland | A1 | |
| TW590741B | Taiwan Province of China | B | |
| CN1547911A | China | A | |
| CN1212768C | China | C | |
| US2006172981A1 | United States of America | A1 | |
| KR100613238B1 | Republic of Korea | B1 | |
| US7115593B2 | United States of America | B2 | |
| US7208510B2 | United States of America | B2 | |
| US2007161688A1 | United States of America | A1 | |
| IL149554AThis record | Israel | A | |
| PL200668B1 | Poland | B1 | |
| CZ301233B6 | Czechia | B6 | |
| CN101627772A | China | A | |
| US7956009B2 | United States of America | B2 |
2 legal events, as the office reported them to INPADOC
Over the term
Point at a mark for the eventEvents
| Event | Code | |
|---|---|---|
| Patent not in force due to non-payment of renewal feesMM9K | MM9K | |
| Patent renewedKB | KB |
Numbers
- Publication, DOCDB
- 149554
- Publication, EPODOC
- IL149554
- Application
- 149554
- Application, DOCDB
- 14955402
- Application, EPODOC
- IL20020149554
Titles
- English
- FUNGICIDAL COMBINATIONS OF ACTIVE SUBSTANCES
Classification
- CPC, 1
- A01N47/12
- IPC, 1
- A01N47 12
