IP Library Granted Patent US 10,188,106
Granted Patent B2
US 10,188,106 · App. 14/716,704 · Granted Jan 29, 2019

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

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Quick Facts
Patent No.
US 10,188,106
App. No.
14/716,704
Granted
Jan 29, 2019
Kind
B2
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 (45)

1. A composition comprising:

A) a tetrazolyloxime derivative of formula (I)

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 1 ) or (A 2 ):

wherein Y represents an alkyl group; and

Het represents a pyridyl group of formula (Het 1 ) or a thiazolyl group of formula (Het 2 );

wherein R represents a hydrogen atom or a halogen atom; Z represents a hydrogen atom, an amino group, 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 fungicide compound in an A/B weight ratio ranging from 1/0.01 to 1/100;

wherein said fungicide is selected from the group consisting of azoxystrobin, bixafen, boscalid, chlorothalonil, clothianidin, cymoxanil, dimethomorph, fluazinam, fludioxonil, fluopicolide, fluoxastrobin, fosetyl-Al, imidacloprid, ipconazole, iprodione, iprovalicarb, isopyrazam, mancozeb, metalaxyl, metalaxyl-M (mefenoxam), metconazole, penthiopyrad, propamocarb-HCl, propineb, prothioconazole, pyraclostrobin, tebuconazole, trifloxystrobin, triticonazole, and N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide.

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 6 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 (Het1) 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 , wherein the composition comprises:

A) pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate; and

B) metalaxyl.

14. The composition according to claim 13 , wherein said composition is synergistically effective.

15. The composition according to claim 1 , comprising:

A) a tetrazolyloxime derivative of formula (I)

wherein

X represents a hydrogen atom;

A represents a tetrazoyl group of formula (A 1 ):

wherein Y represents an alkyl group; and

Het represents a pyridyl group of formula (Het 1 ):

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.

16. The composition according to claim 1 , wherein

A is tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate; and

B is selected from the group consisting of isopyrazam, penthiopyrad, ipconazole, metconazole, triticonazole, metalaxyl, metalaxyl-M (mefenoxam), fluopicolide dimethomorph, fluoxastrobin.

17. 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; and

B is selected from the group consisting of fosetyl-Al, mancozeb, propineb, iprovalicarb, chlorothalonil, clothianidin, cymoxanil, imidacloprid, propamocarb-HCl, azoxystrobin, bixafen, fluoxastrobin, N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, prothioconazole, pyraclostrobin, tebuconazole, trifloxystrobin, boscalid, fluazinam, fludioxonil and iprodione.

18. The composition according to claim 1 , wherein the fungicide compound B is selected from the group consisting of dimethomorph, fluopicolide, fluoxastrobin, ipconazole, isopyrazam, metalaxyl, metalaxyl-M (mefenoxam), metconazole, penthiopyrad, and triticonazole.

19. 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.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 3, 2018
From: COQUERON, PIERRE-YVES; GROSJEAN-COURNOYER, MARIE-CLAIRE; HUTIN, PIERRE; SPICA, GILBERT; VOERSTE, ARND; WACHENDORFF-NEUMANN, ULRIKE
To: BAYER CROPSCIENCE AG
Reel/Frame 047655/0008 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2018
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Reel/Frame 047403/0243 →
NUNC PRO TUNC ASSIGNMENT Recorded Feb 3, 2016
From: BAYER CROPSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 037689/0656 →