IP Library Granted Patent US 8,597,688
Granted Patent B2
US 8,597,688 · App. 13/003,032 · Granted Dec 3, 2013

Pesticidal mixtures comprising isoxazoline compounds II

Inventors: Karsten Koerber (Eppelheim, DE); Florian Kaiser (Mannheim, DE); Egon Haden (Ludwigshafen, DE)
Assignee: BASF SE
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Quick Facts
Patent No.
US 8,597,688
App. No.
13/003,032
Granted
Dec 3, 2013
Kind
B2
Abstract

The present invention relates to pesticidal mixtures comprising as active components 1) at least one isoxazoline compound I of the formula I wherein R 1 , R 2 , R 3 , R 4 , R 5 and A are defined as in the description; and 2) at least one fungicidal compounds II selected from azoles, strobilurins, carboxamides, carbamates, heterocyclic and various other compounds as defined in the description, in synergistically effective amounts. The invention relates further to methods and use of these mixtures for combating insects, arachnids or nematodes and harmful fungis in and on plants, and for protecting such plants being infested with pests, especially also for protecting seeds.

Claims (95)

1. A pesticidal mixture comprising at least two active compounds,

wherein:

1) at least one active compound I is a isoxazoline compound of the formula (I)

wherein

A is

and wherein #denotes the bond in formula I;

R 1 , R 3 are independently from one another selected from the group consisting of hydrogen, chloro and CF 3 ;

R 2 is hydrogen or chloro;

R 4 is hydrogen or CH 3 ,

R 5 is hydrogen,

or

R 4 and R 5 are together a bridging 1,3-butadienyl group, which form—together with the aromatic phenylring C they are attached to—a naphthyl ring;

or the tautomers, enantiomers, diastereomers or salts thereof,

and

2) at least one active compound II is a fungicidal compound selected from the groups IIA to IIF:

IIA an azole selected from the group consisting of triazoles, imidazoles, pyrazoles, thiazoles and oxazoles selected from the group consisting of benomyl, carbendazim, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, prochloraz, prothioconazole, tebuconazole, and triticonazole;

IIB a strobilurin selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin, and trifloxystrobin;

IIC a carboxamide selected from the group consisting of bixafen, boscalid, carpropamid, dimethomorph, fenhexamid, fluopyram, flumorph, fluopicolide (picobenzamid), mandipropamid, metalaxyl, mefenoxam, ofurace, penthiopyrad, and zoxamide;

IID a heterocyclic compound selected from the group consisting of dodemorph, famoxadone, fenpropidin, fenpropimorph, proquinazid, pyrimethanil, quinoxyfen, tridemorph, vinclozolin, and 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;

IIE a carbamate selected from the group consisting of flubenthiavalicarb, iprovalicarb, mancozeb, maneb, metiram, and thiram;

IIF a fungicide selected from

the group of sulfur-containing heterocyclyl compounds comprising dithianon;

the group of organophosphorus compounds comprising fosetyl-aluminum, and phosphorous acid and its salts;

the group of organochlorine compounds comprising chlorothalonil, flusulfamide, and thiophanate-methyl;

wherein the compound of formula (I) and compound II are present in a weight ratio of 500:1 to 1:100.

2. The pesticidal mixture according to claim 1 comprising additionally one or more further insecticidal compound III.

3. The pesticidal mixture according to claim 1 , wherein the substituents of the compound I of formula (I) have the following meanings:

A is A-1, A-4 or A-6;

R 1 , R 3 are independently from one another selected from the group consisting of hydrogen, chloro and CF 3 ;

R 2 is hydrogen or chloro;

R 4 is hydrogen or CH 3 ,

R 5 is hydrogen

or

R 4 and R 5 are together a bridging 1,3-butadienyl group, which form—together with the aromatic phenylring C they are attached to—a naphthyl ring;

or the tautomers, enantiomer, diastereomer or salts thereof.

4. The pesticidal mixture according to claim 1 , wherein the substituents of the compound I of formula (I) have the following meanings:

A is A-1, A-4 or A-6;

R 1 , R 2 , R 3 are chloro;

R 4 or is hydrogen CH 3 ,

R 5 is hydrogen

or

R 4 and R 5 are together a bridging 1,3-butadienyl group, which form—together with the aromatic phenylring C they are attached to—a naphthyl ring;

or the tautomers, enantiomers, diastereomers or salts thereof.

5. The pesticidal mixture according to claim 1 , wherein the substituents of the compound I of formula (I) have the following meanings:

A is A-1, A-4 or A-6;

R 1 , R 3 are chloro;

R 2 is hydrogen;

R 4 is hydrogen or CH 3 ,

R 5 is hydrogen

or

R 4 and R 5 are together a bridging 1,3-butadienyl group, which form—together with the aromatic phenylring C they are attached to—a naphthyl ring;

or the tautomers, enantiomers, diastereomers or salts thereof.

6. The pesticidal mixture according to claim 1 , wherein the substituents of the compound I of formula (I) have the following meanings:

A is A-6;

R 1 , R 3 are chloro;

R 2 is hydrogen;

R 4 is CH 3 ,

R 5 is hydrogen

or

R 4 and R 5 are together a bridging 1,3-butadienyl group, which form—together with the aromatic phenylring C they are attached to—a naphthyl ring;

or the tautomers, enantiomers, diastereomers or salts thereof.

7. The pesticidal mixture according to claim 1 , wherein the substituents of the compound I of formula (I) have the following meanings:

A is A-1, A-4 or A-6;

R 1 , R 3 are CF 3 ;

R 2 is hydrogen;

R 4 is hydrogen or CH 3 ,

R 5 is hydrogen

or

R 4 and R 5 are together a bridging 1,3-butadienyl group, which form—together with the aromatic phenylring C they are attached to—a naphthyl ring;

or the tautomers, enantiomers, diastereomers or salts thereof.

8. The pesticidal mixture according to claim 1 , wherein the substituents of the active compound I of formula I have the following meanings:

A is A-1, A-4 or A-6;

R 1 is CF 3 ;

R 2 , R 3 are hydrogen;

R 4 is hydrogen or CH 3 ,

R 5 is hydrogen

or

R 4 and R 5 are together a bridging 1,3-butadienyl group, which form—together with the aromatic phenylring C they are attached to—a naphthyl ring;

or the tautomers, enantiomers, diastereomers or salts thereof.

9. The pesticidal mixture according to claim 1 , comprising a compound I of the formula (I) and a compound II in a weight ratio of from 100:1 to 1:100.

10. The pesticidal mixture according to claim 1 , comprising an active compound II selected from the group II.A of azoles consisting of benomyl, carbendazim, epoxiconazole, fluquinconazole, flutriafol, flusilazole, metconazole, prochloraz, prothioconazole, tebuconazole and triticonazole.

11. The pesticidal mixture according to claim 1 , comprising an active compound II selected from the group consisting of picoxystrobin, pyraclostrobin and trifloxystrobin.

12. The pesticidal mixture according to claim 1 , comprising an active compound II selected from the group consisting of boscalid, dimethomorph, fenhexamid and penthiopyrad.

13. The pesticidal mixture according to claim 1 , comprising an active compound II selected from the group consisting of dodemorph, famoxadone, fenpropimorph, iprodione, proquinazid, pyrimethanil, tridemorph and 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine.

14. The pesticidal mixture according to claim 1 , comprising an active compound II selected from the group consisting of maneb, mancozeb, metiram and thiram.

15. The pesticidal mixture according to claim 1 , comprising an active compound II selected from the group consisting of chlorothalonil, dithianon, flusulfamide, metrafenone and phosphorous acid and its salts.

16. A ternary or quaternary pesticidal mixture according to claim 1 , comprising two active compounds II.

17. A pesticidal composition, comprising a liquid or solid carrier and a mixture of at least one active compound I and at least one active compound II according to claim 1 .

18. A method for controlling phytopathogenic harmful fungi, wherein the fungi, their habitat or the plants to be protected against fungal attack, the soil or seed are treated with an effective amount of a mixture of at least one active compound I and at least one active compound II according to claim 1 .

19. A method for protecting plants from phytopathogenic harmful fungi, wherein the fungi, their habitat or the plants to be protected against fungal attack, the soil or seed are treated with an effective amount of a mixture of at least one active compound I and at least one active compound II according to claim 1 .

20. A method according to claim 18 , wherein the mixture is applied in an amount of from 5 g/ha to 2000 g/ha.

21. A method for protection of seed comprising contacting the seeds with an effective amount of a mixture of at least one active compound I and at least one active compound II according to claim 1 .

22. A method according to claim 21 wherein the mixture of the active compound I and the active compound II is applied in an amount of from 0.001 g to 10 kg per 100 kg of seeds.

23. A seed treated with the mixture of at least one active compound I and at least one active compound II according to claim 1 in an amount of from 0.1 g to 10 kg per 100 kg of seeds.

24. A method according to claim 18 , wherein the active compound I and the active compound II are applied simultaneously, that is jointly or separately, or in succession.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 30, 2013
From: KOERBER, KARSTEN; KAISER, FLORIAN; HADEN, EGON
To: BASF SE
Reel/Frame 030900/0560 →
Continuity (2)
Provisional Application 61079311 · Jul 9, 2008
Related Publication 20110159107A1 · Jun 30, 2011