Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance

Abstract

The present invention relates to a pesticide composition intended for protecting plants, crops or seeds against fungal diseases or insect damages, and the corresponding methods of protection by application of the said composition. More precisely, the subject of the present invention is a pesticide composition based on a tetrazolyloxime derivative and a fungicide or an insecticide active substance or compound.

Claims

1. A composition comprising: A) a tetrazolyloxime derivative of formula (I) ##STR00010## wherein X represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a cyano group, a methanesulfonyl group, a nitro group, a trifluoromethyl group or an aryl group; A represents a tetrazoyl group of formula (A.sup.1) or (A.sup.2): ##STR00011## wherein Y represents an alkyl group; and Het represents a pyridyl group of formula (Het.sup.1) or a thiazolyl group of formula (Het.sup.2) ; ##STR00012## wherein R represents a hydrogen atom or a halogen atom; Z represents a hydrogen atom, an amino group, or a group of formula QC(═O)NH—, wherein Q represents a hydrogen atom; an alkyl group having 1 to 8 carbon atoms; an alkyl group having 1 to 6 carbon atoms substituted by a halogen atom; a cycloalkyl group having 3 to 6 carbon atoms; an alkoxyl group having 1 to 8 carbon atoms; a cycloalkyloxy group having 3 to 6 carbon atoms; a benzyloxy group; a 2-phenylethyloxy group; a thioalkyl group substituted by an alkyl group having 1 to 4 carbon atoms; an alkyl group having 1 to 2 carbon atoms substituted by an alkoxyl group having 1 to 4 carbon atoms; an alkyl group having 1 to 6 carbon atoms substituted by an acylamino group having 1 to 4 carbon atoms; an alkoxy group having 1 to 6 carbon atoms substituted by an acylamino group having 1 to 4 carbon atoms; an alkylamino group having 1 to 8 carbon atoms; an alkenyl group having 2 to 6 carbon atoms; an aralkyl group; or a phenyl group ; and B) a compound B in an A/B weight ratio ranging from 1/0.01 to 1/100, wherein said compound B is fluopyram.

2. A composition according to claim 1, further comprising: C) a second further fungicide compound in an A/B/C weight ratio ranging from 1/0.01/0.01 to 1/100/100.

3. A composition according to claim 1, further comprising: D) an insecticide compound in an A/B/D weight ratio ranging from 1/0.01/0.01 to 1/100/100.

4. A composition according to claim 3 wherein insecticide compound D is selected from the group consisting of imidacloprid and clothianidin.

5. A composition according to claim 1, further comprising: C) a second further fungicide compound and D) an insecticide compound in an A/B/C/D weight ratio ranging from 1/0.01/0.01/1 to 1/100/100/100.

6. A composition according to claim 1 wherein X represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a cyano group, a methanesulfonyl group, a nitro group, a trifluoromethyl group or an aryl group.

7. A composition according to claim 1 wherein X independently represents a chlorine atom, a bromine atom, an iodine atom, a fluorine atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, a propoxy group and an isopropoxy group, a phenyl group, a 4-methylphenyl group, or a 4-chlorophenyl group.

8. A composition according to claim 1 wherein X represents a hydrogen atom.

9. A composition according to claim 1 wherein Y represents a methyl group, an ethyl group, an n-propyl group or an isopropyl group.

10. A composition according to claim 1 wherein R in the pyridyl group of formula (Het.sup.1) represents a hydrogen atom, a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.

11. A composition according to claim 1 wherein Q represents a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a 1,1-dimethylpropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isoamyl group, a 1-methylbutyl group, a 2-methylbutyl group, an neopentyl group, a 1-ethylpropyl group, an n-pentyl group, a hexyl group, a heptyl group, an octyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a difluorochloromethyl group, a pentafluoroethyl group, a 3,3,3-trifluoro-n-propyl group, a 1-chlorohexyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a 1,1-dimethylpropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, an isopentyloxy group, a 1-methylbutoxy group, a 2-methylbutoxy group, an neopentyloxy group, a 1-ethylpropoxy group, an n-pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a methoxymethyl group, an ethoxymethyl group, an ethoxyethyl group, a butoxymethyl group, a methylthiomethyl group, a methylthioethyl group, an ethylthiomethyl group, a butylthiomethyl group, an acetylaminomethoxy group, a 2-(propionylamino)ethoxy group, a 3-(acetylamino)propoxy group, a 3-(propionylamino)propoxy group, a 3-(isopropionylamino)propoxy group, a 3-(butyroylamino)propoxy group, a 3- (isobutyroylamino)propoxy group, a 3-(sec-butyroylamino)propoxy group, a 3-(tert-butyroylamino)propoxy group, a 4-(acetylamino)butoxy group, a 5-(acetylamino)pentyloxy group, a 6-(acetylamino)hexyloxy group, an acetylaminomethyl group, a 2-(propionylamino)ethyl group, a 3-(acetylamino)propyl group, a 3-(propionylamino)propyl group, a 3-(isopropionylamino)propyl group, a 3-(butyroylamino)propyl group, a 3-(isobutyroylamino)propyl group, a 3-(sec-butyroylamino)propyl group, 3-(tert-butyroylamino)propyl group, a 4-(acetylamino)butyl group, a 5-(acetylamino)pentyl group, a 6-(acetylamino)hexyl group, methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, a butylamino group, an isobutylamino group, a sec-butylamino group, a tert-butylamino group, an neopentylamino group, a 1-ethylpropylamino group, an n-pentylamino group, a hexylamino group, a heptylamino group, an octylamino group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-pentenyl group, a 5-hexenyl group, a benzyl group or a phenethyl group.

12. A composition according to claim 1 wherein the A/B weight ratio ranges from 1/0.05 to 1/80.

13. The composition according to claim 1, comprising: A) a tetrazolyloxime derivative of formula (I) ##STR00013## wherein X represents a hydrogen atom; A represents a tetrazoyl group of formula (A.sup.1): ##STR00014## wherein Y represents an alkyl group; and Het represents a pyridyl group of formula (Het.sup.1): ##STR00015## wherein R represents a hydrogen atom or a halogen atom; and Z represents a group of formula QC(═O)NH— wherein Q represents an alkoxyl group having 1 to 8 carbon atoms.

14. The composition according to claim 1, wherein A is pentyl{6—[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy) methyl] pyridin-2-yl}carbamate.

15. A method for controlling the phytopathogenic fungi or damaging insects of plants, crops or seeds comprising the application of an agronomically effective and substantially non-phytotoxic quantity of a pesticide composition according to claim 1 as seed treatment, foliar application, stem application, drench or drip application or chemigation to the seed, the plant or to the fruit of the plant or to soil or to inert substrate, Pumice, Pyroclastic materials or stuff, synthetic organic substrates organic substrates or to a liquid substrate wherein the plant is growing or wherein it is desired to grow.

Description

EXAMPLE A

Phytophthora Test (Tomatoes)/Protective

(1) Solvent: 24.5 parts by weight of acetone

(2) 24.5 parts by weight of dimethylacetamide

(3) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(4) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water ro to the desired concentration.

(5) To test for protective activity, young plants are sprayed with the preparation of active compound at the stated rate of application. 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 cabinet at approximately 20° C. and a relative atmospheric humidity of 100%.

(6) The test is evaluated 3 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

(7) The tables below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

(8) Phytoplithora Test (Tomatoes)/Protective

(9) TABLE-US-00003 Rate of application Active compound of active compound Efficacy Known: in ppm in % formula 1: pentyl {6-[({[(1-methyl-1H-tetrazol-5- 1 77 yl)(phenyl)methylidene]aminol}oxy)methyl]pyridin-2- 0.5 57 yl}carbamate 0.25 47 fosetyl-Al 10 0 mancozeb 10 0 Ppopineb 10 0 iprovalicarb 1 16 chlorothalonil 25 44

(10) TABLE-US-00004 Inventive Compound combination: Rate of Expected application value, cal- Ratio of active culated using of the compound Actual Colby's mixture in ppm efficacy formula formula 1 + } 1:10 1 + 10 } 91 77 fosetyl-Al formula 1 + } 1:10 1 + 10 } 93 77 mancozeb formula 1 + } 1:10 1 + 10 } 93 77 propineb formula 1 + } 1:2  0.5 + 1 }  78 64 iprovalicarb formula 1 +  } 1:100 0.25 + 25 }   83 70 chlorothalonil

EXAMPLE B

Venturia Test (Apples)/Protective

(11) Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaiyl polyglycol ether

(12) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

(13) To test for protective activity, young plants are sprayed with the preparation of active compound the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab (Venturia inaequalis) and then remain for 1 day in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%.

(14) The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%.

(15) The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

(16) The tables below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

(17) Venturia Test (Apples)/Protective

(18) TABLE-US-00005 Rate of application Active compound of active compound Efficacy Known: in ppm in % formula 1: pentyl {6-[({[(1-methyl-1H-tetrazol-5- 100 8 yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2- yl}carbamate clothianidin 100 66 cymoxanil 100 23 imidacloprid 100 4 propamocarb-HCl 100 4
Venturia Test (Apples)/Protective

(19) TABLE-US-00006 Inventive Compound combination: Rate of Expected application value, cal- Ratio of active culated using of the compound Actual Colby's mixture in ppm efficacy formula formula 1 + } 1:1 100 + 100 } 86 69 clothianidin formula 1 + } 1:1 100 + 100 } 63 29 cymoxanil formula 1 + } 1:1 100 + 100 } 67 12 imidacloprid formula 1 + } 1:1 100 + 100 } 59 12 propamo- carb-HCl

EXAMPLE C

Alternaria Test Protective

(20) Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(21) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

(22) To test for protective activity, young plants are sprayed with the preparation of active compound the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants are then placed in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%.

(23) The test is evaluated 3 days after the inoculation, 0% means an efficacy which corresponds to that of the control while an efficacy of 100% means that no disease is observed.

(24) The tables below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

(25) Alternaria Test (Tomatoes)/Protective

(26) TABLE-US-00007 Rate of application Active compound of active compound Efficacy Known: in ppm in % formula 1: pentyl {6-[({[(1-methyl-1H-tetrazol-5- 100 0 yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2- 50 8 yl}carbamate 25 0 10 5 0 0 azoxystrobin 10 15 bixafen 1.25 65 chlorothalonil 50 71 cymoxanil 50 23 fluoxastrobin 10 15 imidacloprid 25 0 N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl 1 18 1H-pyrazole-4-carboxamide propamocarb-HCl 50 38 prothioconazole 2.5 23 pyraclostrobin 10 45 tebuconazole 10 55 trifloxystrobin 10 35
Alternaria Test (Tomatoes)/Protective

(27) TABLE-US-00008 Inventive Compound combination: Rate of Expected application value, cal- Ratio of active culated using of the compound Actual Colby's mixture in ppm efficacy formula formula 1 +  } 10:1 100 + 10 }  45 15 azoxystrobin formula 1 + } 4:1 5 + 1.25 }  83 65 bixafen formula 1 + } 1:1 50 + 50 } 83 73 chlorothalonil formula 1 + } 1:1 50 + 50 } 50 29 cymoxanil formula 1 +  } 10:1 100 + 10 }  40 15 fluoxastrobin formula 1 + } 1:1 25 + 25 } 46 0 imidacloprid formula 1 +  } 10:1  10 + 1 } 42 18 N-[2-(1,3- dimethyl- butyl)phenyl]-5- fluoro-1,3- dimethyl-1H- pyrazole-4- carboxamide
Alternaria Test (Tomatoes)/Protective

(28) TABLE-US-00009 Inventive Compound combination: Rate of Expected application value, cal- Ratio of active culated using of the compound Actual Colby's mixture in ppm efficacy formula formula 1 + } 1:1   50 + 50 } 58 43 propamocarb-HCl formula 1 + } 10:1  25 + 2.5 } 40 23 prothioconazole formula 1 + } 10:1 100 + 10 } 55 45 pyraclostrobin formula 1 + } 10:1 100 + 10 } 65 55 tebuconazole formula 1 + } 10:1 100 + 10 } 50 35 trifloxy- strobin

EXAMPLE D

Botrytis Test (Beans)/Protective

(29) Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaiyl polyglycol ether

(30) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

(31) To test for protective activity, young plants are sprayed with the preparation of active compound After the spray coating has dried on, 2 small pieces of agar covered with growth of Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at 20oC and a relative atmospheric humidity of 100%.

(32) 2 days after the inoculation, the size of the lesions on the leaves is evaluated. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.

(33) The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

(34) Botrytis Test (Beans)/Protective

(35) TABLE-US-00010 Rate of application Active compound of active compound Efficacy Known: in ppm in % formula 1: pentyl {6-[({[(1-methyl-1H-tetrazol-5- 100 4 yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2- 50 4 yl}carbamate boscalid 5 21 fluazinam 10 79 fludioxonil 5 45 iprodione 100 66
Bot

(36) TABLE-US-00011 Inventive Compound combination: Rate of Expected application value, cal- Ratio of active culated using of the compound Actual Colby's mixture in ppm efficacy formula formula 1 + } 10:1 50 + 5 } 53 24 boscalid formula 1 + } 10:1 100 + 10 }  94 80 fluazinam formula 1 + } 10:1 50 + 5 } 73 47 fludioxonil formula 1 + } 1:1  100 + 100 }   90 67 iprodione