Claims
- 1. A method of combating phytopathogenic diseases on crop plants which comprises applying to the crop plants or the locus thereof being infested with said phytopathogenic disease an effective amount of a combination ofa) a 2-(5-phenyl-3,6-diaza-2,7-dioxa-octa-3,5-dienyl)-phenylacrylamide of formula I whereinR1 is hydrogen, fluoro or chloro, R2 is methyl, ethyl, trifluoromethyl, trifluoromethoxy, cyano, fluoro, chloro or bromo, with the proviso that R2 cannot be fluoro, chloro or bromo, when R1 is hydrogen; in association with b) either an anilinopyrimidine of formula II whereinR3 is methyl, 1-propynyl or cyclopropyl; or an azole of formula III whereinA is selected from whereby the β-carbon attaches to benzene ring of formula III, and whereinR4 is H, F, Cl, 4-fluorophenoxy or 4-chlorophenoxy; R5is H, Cl or F; R6 and R7 are independently H or CH3; R8 is C1-4alkyl or cyclopropyl; R9 is 4-chlorophenyl or 4-fluorophenyl; R10 is phenyl, and R11 is allyloxy, C1-4alkyl, or 1,1,2,2-tetrafluoroethoxy-methyl, and the salts of such azole fungicide; or a morpholine fungicide of formula IV whereinR12 is C8-15cycloalkyl, C8-15alkyl, or C1-4alkylphenyl-C1-4alkyl, and the salts of such morpholine fungicide; or a strobilurin compound of formula V whereinX is NH or O, Y is CH or N, and R13 is 2-methylphenoxy-methyl, 2,5-dimethylphenoxy-methyl, 4-(2-cyanophenoxy)-pyrimidin-6-yloxy, or 4-(3-trifluoromethylphenyl)-3-aza-2-oxa-4-pentenyl; or a pyrrole compound of the formula VI whereinR14 and R15 are indendently halo, or together from a perhalomethylendioxo bridge; or a phenylamide of the formula VII whereinR16 is benzyl, methoxymethyl, 2-furanyl or chloromethyl, R17 is 1-methoxycarbonyl-ethyl, or Z is CH or N; or a dithiocarbamate fungicide selected from mancozeb, maneb, metiram and zineb; or a copper compound selected from copper hydroxide, copper oxychloride, copper sulfate and oxine-copper; or sulfur; or a phthalimide compound of the formula VIII whereinR18 and R19 together form a 4-membered bridge —CH2—CH═CH—CH2— or ═CH—CH═CH—CH═; or with the compound of formula IX or with the compound of formula X or with the compound of formula XI or with the compound of formula XII or with the compound of formula XIII or with the compound of formula XIV or with the compound of formula XV or with the compound of formula XVI or with the compound of formula XVII or with the compound of formula XVIII or with the compound of formula XIX or with the compound of formula XX or with the compound of formula XXI or with the compound of formula XXII or with the compound of formula XXIII or with the compound of formula XXIV or with 2-chloro- N-(4′-fluoro-1,1′-biphenyl-2-yl)nicotinamide (compound XXV), or with 2-chloro- N-(4′-chloro-1,1′-biphenyl-2-yl)nicotinamide (compound XXVI), or with methyl N-(2-[1-(4-chlorophenyl)pyrazol-3-yloxymethyl]phenyl)-N-methoxycarbamate (compound XXVII), or with methyl N-(2-[1-(4-tolyl)pyrazol-3-yloxymethyl]phenyl)-N- methoxycarbamate (compound XXVIII), or with 2-[4-methoxy-3-(1-methylethoxy)-1,4-diazabuta-1,3-dienyloxymethyl]phenyl-2-methoximino-N-methylacetamide (compound XXIX), or with 2-[4-methoxy-3-(1-methylpropoxy)-1,4-diazabuta-1,3-dienyloxymethyl]phenyl-2-methoximino-N-methylacetamide (compound XXX), or with N-(cyclopropylmethoxy)-N′-(2-phenylacetyl)-2,3-difluoro-6-trifluoromethyl-benzamidine (compound XXXI), or with N-[3′-(1′-chloro-3-methyl 2′-oxopentan)]-3,5-dichloro-4-methylbenzamide (compound XXXII), or with methyl(2)-2-{6-[6-(trifluoromethyl)pyrid-2-yloxymethyl]-phenyl}-3-methoxyacrylate (compound XXXIII), or with 2-chloro-4-(2-fluoro-2-methylpropionylamino)-N,N-dimethylbenzamide (compound XXXIV), or with (S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one (compound XXXV), or with N-methyl-2-{2-[α-methyl-3-(trifluoromethyl)benzyloximinomethyl]phenyl}-2-methoximinoacetamide (compound XXXVI), or with a (S)-valinamide of formula XXXVII) whereinR20 is isopropyl, sec.-butyl or tert.-butyl, and R21 is 4-chlorophenyl, 4-tolyl, 4-methoxyphenyl or β-naphthyl, or with a (S)-valinamide of formula XXXVIII whereinR20 is isopropyl, sec.-butyl or tert.-butyl, R22 is halogen, methyl or methoxy, and n is 0, 1, or 2; or with an azole of formula XXXIX whereinR23 is chloro or fluoro, and R24 is hydrogen or methyl.
- 2. A method according to claim 1 wherein component b) does not comprise the compounds of formulae XXV to XXXVIII.
- 3. A method according to claim 1 wherein the component a) comprises a compound of the formula I wherein R1 is fluoro or chloro and R2 is methyl, trifluoromethyl, fluoro, chloro or bromo, or wherein R1 is fluoro or chloro and R2 is methyl, chloro or fluoro, or wherein R1 and R2 are independently fluoro or chloro, or wherein R1 is hydrogen, fluoro or chloro and R2 is methyl, fluoro or chloro, provided that R2 is methyl when R1 is hydrogen.
- 4. A method according to claim 1 wherein the component b) is selected from the group comprising pyrimethanil, cyprodinil, cyproconazole, hexaconazole; difenoconazole, etaconazole, propiconazole, tebuconazole, triticonazole, flutriafol, epoxiconazole, fenbuconazole, bromuconazole, penconazole, imazalil, tetraconazole, flusilazole, metconazole, diniconazole, fluquinconazole, myclobutanil, triadimenol, dodemorph, tridemorph, fenpropimorph, mancozeb, maneb, metiram, zineb, copper hydroxide, copper oxychloride, copper sulfate, oxine-copper, sulfur, kresoxim-methyl, azoxystrobin, 2-[2-(2,5-dimethoxyphenoxy-methyl)-phenyl]-2-methoximino-acetic acid N-methyl-amide, methyl 2-{2-[4-(3-trifluoromethylphenyl)-3-aza-2-oxa-4-pentenyl]-phenyl}-2-methoxyimino-acetate, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, orfurace, oxadixyl, captan, folpet, prochloraz, triflumizole, pyrifenox, acibenzolar-S-methyl, chlorothalonil, cymoxanil, dimethomorph, famoxadone, fenhexamide, fenarimol, fluazinam, fosetyl-aluminium, quinoxyfen, fenpropidine, spiroxamine, and carbendazime.
- 5. A method according to claim 1 wherein the component b) is fenamidone or iprovalicarb.
- 6. A method according to claim 4 wherein component b) is selected from a group comprising cyproconazole, hexaconazole; difenoconazole, propiconazole, tebuconazole, flutriafol, epoxiconazole, fenbuconazole, bromuconazole, penconazole, tetraconazole, flusilazole, metconazole, diniconazole, triadimenol, fluquinconazole and prochloraz.
- 7. A method according to claim 4 wherein component b) is selected from a group comprising cyprodinil, tridemorph, fenpropimorph, kresoxim-methyl, azoxystrobin, methyl 2-{2-[4-(3-trifluoromethylphenyl)-3-aza-2-oxa-4-pentenyl]-phenyl}-2-methoxyimino-acetate, acibenzolar-S-methyl, chlorothalonil, famoxadone, quinoxyfen, fenpropidine and carbendazime.
- 8. A method according to claims 4, 6 or 7 wherein component a) is selected from the group consisting of a 2-(5-phenyl-3,6-diaza-2,7-dioxa-octa3,5-dienyl)-phenylacrylamide compound of formula I wherein R1 is hydrogen and R2 is 4-CH3 (1.03), R1 is 2-Cl and R2 is 4-Cl (1.03), R1 is hydrogen and R2 is 4-OCF3, R1 is 2-F and R2 is 4-CH3, R1 is 2-F and R2 is 4-F, R1 is 2-Cl and R2 is 4-F and R1 is 2-F and R2 is 4-Cl.
- 9. A method according to claim 1 wherein component b) is the compound isopropyl 2-methyl-1-[(1-p-tolylethyl)carbamoyl]-(S)-propylcarbamate (compound XXXVIIa).
- 10. A method according to claim 4 wherein component b) is selected from the group consisting of cyprodinil, fenpropimorph, kresoxim-methyl, azoxystrobin, methyl 2-{2-[4-(3-trifluoromethylphenyl)-3-aza-2-oxa-4-pentenyl]-phenyl}-2-methoxyimino-acetate, acibenzolar-S-methyl and fenpropidine.
- 11. A method according to claim 6 wherein component b) is selected from the group consisting of propiconazole, difenoconazole, penconazole, tebuconazole, prochloraz, epoxiconazole and cyproconazole.
- 12. A fungicidal composition comprising a fungicidally effective combination of the componentsa) a 2-(5-phenyl-3,6-diaza-2,7-dioxa-octa-3,5dienyl)-phenylacrylamide of formula I whereinR1 is hydrogen, fluoro or chloro, R2 is methyl, ethyl, trifluoromethyl, trifluoromethoxy, cyano, fluoro, chloro or bromo, with the proviso that R2 cannot be fluoro, chloro or bromo, when R1 is hydrogen; and b) either an anilinopyrimidine of formula II whereinR3 is methyl, 1-propynyl or cyclopropyl; or an azole of formula III whereinA is selected from whereby the β-carbon attaches to benzene ring of formula III, and whereinR4 is H, F, Cl, 4-fluorophenoxy or 4-chlorophenoxy; R5 is H, Cl or F; R6 and R7 are independently H or CH3; R8 is C1-4alkyl or cyclopropyl; R9 is 4-chlorophenyl or 4-fluorophenyl; R10 is phenyl, and R11 is allyloxy, C1-4alkyl, or 1,1,2,2-tetrafluoroethoxy-methyl, and the salts of such azole fungicide; or a morpholine fungicide of formula IV whereinR12 is C8-15cycloalkyl, C8-15alkyl, or C1-4alkylphenyl-C1-4alkyl, and the salts of such morpholine fungicide; or a strobilurin compound of formula V whereinX is NH or O, Y is CH or N, and R13 is 2-methylphenoxy-methyl, 2,5-dimethylphenoxy-methyl, 4-(2-cyanophenoxy)-pyrimidin-6-yloxy, or 4-(3-trifluoromethylphenyl)-3-aza-2-oxa-4pentenyl; or a pyrrole compound of the formula VI whereinR14 and R15 are indendently halo, or together from a perhalomethylendioxo bridge; or a phenylamide of the formula VII whereinR16 is benzyl, methoxymethyl, 2-furanyl or chloromethyl, R17 is 1-methoxycarbonyl-ethyl, or Z is CH or N; or a dithiocarbamate fungicide selected from mancozeb, maneb, metiram and zineb; or a copper compound selected from copper hydroxide, copper oxychloride, copper sulfate and oxine-copper; or sulfur; or a phthalimide compound of the formula VIII whereinR18 and R19 together form a 4-membered bridge —CH2—CH═CH—CH2— or ═CH—CH═CH—CH═; or with the compound of formula IX or with the compound of formula X or with the compound of formula XI or with the compound of formula XII or with the compound of formula XIII or with the compound of formula XIV or with the compound of formula XV or with the compound of formula XVI or with the compound of formula XVII or with the compound of formula XVIII or with the compound of formula XIX or with the compound of formula XX or with the compound of formula XXI or with the compound of formula XXII or with the compound of formula XXIII or with the compound of formula XXIV or with 2-chloro- N-(4′-fluoro-1,1′-biphenyl-2-yl)nicotinamide (compound XXV), or with 2-chloro- N-(4′-chloro-1,1′-biphenyl-2-yl)nicotinamide (compound XXVI), or with methyl N-(2-[1-(4-chlorophenyl)pyrazol-3-yloxymethyl]phenyl)-N-methoxycarbamate (compound XXVII), or with methyl N-(2-[1-(4-tolyl)pyrazol-3-yloxymethyl]phenyl)-N-methoxycarbamate (compound XXVIII), or with 2-[4-methoxy-3-(1-methylethoxy)-1,4-diazabuta-1,3-dienyloxymethyl]phenyl-2-methoximino-N-methylacetamide (compound XXIX), or with 2-[4-methoxy-3-(1-methylpropoxy)-1,4-diazabuta-1,3-dienyloxymethyl]phenyl-2-methoximino-N-methylacetamide (compound XXX), or with N-(cyclopropylmethoxy)-N′-(2-phenylacetyl)-2,3-difluoro-6-trifluoromethyl-benzamidine (compound XXXI), or with N-[3′-(1′-chloro-3-methyl 2′-oxopentan)]-3,5-dichloro4-methylbenzamide (compound XXXII), or with methyl(2)-2-{6-[6-(trifluoromethyl)pyrid-2-yloxymethyl]-phenyl}-3-methoxyacrylate (compound XXXIII), or with 2-chloro-4(2-fluoro-2-methylpropionylamino)-N,N-dimethylbenzamide (compound XXXIV), or with (S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one (compound XXXV), or with N-methyl-2-{2-[α-methyl-3-(trifluoromethyl)benzyloximinomethyl]phenyl}2-methoximinoacetamide (compound XXXVI), or with a (S)-valinamide of formula XXXVII) whereinR20 is isopropyl, sec.-butyl or tert.-butyl, and R21 is 4-chlorophenyl, 4-tolyl, 4-methoxyphenyl or β-naphthyl or with a (S)-valinamide of formula XXXVIII whereinR20 is isopropyl, sec.-butyl or tert.-butyl, R22 is halogen, methyl or methoxy, and n is 0, 1, or, 2; or with an azole of formula XXXIX whereinR23 is chloro or fluoro, and R24 is hydrogen or methyl; together with an agriculturally acceptable carrier, and optionally a surfactant.
- 13. A composition according to claim 12 wherein the weight ratio of a) to b) is between 10:1 and 1:400.
- 14. A fungicidal composition according to claim 12 wherein component b) is the compound isopropyl 2-methyl-1-[(1-p-tolylethyl)carbamoyl]-(S)-propylcarbamate (compound XXXVIIa).
Priority Claims (1)
Number |
Date |
Country |
Kind |
9718366 |
Aug 1997 |
GB |
|
Parent Case Info
This Appln is a 371 of PCT/EP98/05453 filed Aug. 27, 1998.
PCT Information
Filing Document |
Filing Date |
Country |
Kind |
102e Date |
371c Date |
PCT/EP98/05453 |
|
WO |
00 |
2/28/2000 |
2/28/2000 |
Publishing Document |
Publishing Date |
Country |
Kind |
WO99/11125 |
3/11/1999 |
WO |
A |
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