Herbicide-safener combination based on isoxazoline carboxylate safeners

1. A herbicide safener combination comprising

A) an effective amount of a compound of the formula (I) or a salt thereof,

in which

R 1 is phenyl which is unsubstituted or substituted,

R 2 is (C 1 –C 6 )alkyl, (C 3 –C 6 )cycloalkyl or phenyl, each of the 3 last-mentioned radicals is unsubstituted or substituted,

R 3 is hydrogen or a hydrocarbon radical having 1 to 18 C-atoms which is unsubstituted or substituted,

and

B) a herbicide selected from the group consisting of

(B1) Triazolopyrimidine derivatives (B1-1) and (B 1-2)

(B1-1) N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-1,2,4triazolo[1,5-c]pyrimidin-2-sulfonamide (florasulam),

(B-1-2) methyl 3-chloro-(5-ethoxy-7-fluoro[1,2,4]triazole-[1,5-c]pyrimidin-2-ylsulfonamido)-benzoate (cloransulam)

(B2) plant hormone-type herbicides (B2-1) to (B2-4)

(B2-1) 3,6-dichloro-2-methoxy-benzoic acid and salts and esters thereof; (dicamba),

(B2-2) 2-{1-[4-(3,5-difluorophenyl)semicarbazono]ethyl}nicotinic acid and salts thereof (diflufenzopyr);

(B2-3) 3,5,6-trichloro-2-pyridyloxyacetic acid (triclopyr);

(B2-4) 4-amino-3,5-dichloro-6-fluoro-2-pyridyloxyacetic acid and salts and esters thereof (fluroxypyr); and

(B3-1) 4-amino-6-tert-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one (metribuzin);

(B4-1) ethyl (RS)-2-chloro-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]propionate (carfentrazone-ethyl)

(B5) chloroacetanilides (B5-1) to (B5-4)

(B5-1) 2-chloro-N-(2-ethyl-6-methylphenyl)-N-[( 1 S)-2-methoxy-1-methylethyl)]-acetamide (S-metolachlor),

(B5-2) (RS)-2-chloro-N-(2,4-diethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide (dimethenamid),

(B5-3) (S)-2-chloro-N-(2,4-diethyl-3-thienyl)-N-(2-methoxy-1-methylethyl)acetamide (dimethenamid-P), and

(B5-4) 4′-fluoro-N-isopropyl-2-[5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy]acetanilide (flufenacet) and

mixtures of the above herbicides, optionally in combination with other herbicidal active ingredients.

2. A combination as claimed in claim 1 wherein in formula (I)

R 1 is phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, amino, (C 1 –C 4 )haloalkyl, (C 1 –C 4 )haloalkoxy, (C 1 –C 4 )alkyl, (C 1 –C 4 )alkoxy, mono(C 1 –C 4 )alkyl-amino, di(C 1 –C 4 )alkyl-amino, (C 1 –C 4 )alkylthio and (C 1 –C 4 )alkylsulfonyl,

R 2 is (C 1 –C 6 )alkyl, (C 3 –C 6 )cycloalkyl or phenyl, each of the 3 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, amino, (C 1 –C 4 )haloalkyl, (C 1 –C 4 )haloalkoxy, (C 1 –C 4 )alkyl, (C 1 –C 4 )alkoxy, mono(C 1 –C 4 )alkyl-amino, di(C 1 –C 4 )alkyl-amino, (C 1 –C 4 )alkylthio and (C 1 –C 4 )alkylsulfonyl,

R 3 is hydrogen or a hydrocarbon radical having 1 to 18 C-atoms which is unsubstituted or substituted by one or more radicals selected from the group consisting of

halogen, cyano, thio, nitro, hydroxyl, (C 1 –C 6 )alkyl, (C 1 –C 6 )haloalkyl, the 2 last-mentioned radicals as substituents of cyclic radicals only, (C 1 –C 6 )alkoxy, (C 2 –C 6 )alkenyloxy, (C 2 –C 6 )alkinyloxy, (C 1 –C 6 )haloalkoxy, (C 2 –C 6 )alkylthio, (C 3 –C 6 )cycloalkyl, (C 3 –C 6 )cycloalkoxy, (C 1 –C 8 )alkoxy-carbonyl, (C 2 –C 6 )alkenyloxy-carbonyl, (C 2 –C 6 )alkinyloxy-carbonyl, (C 1 –C 8 )alkyl-carbonyl, (C 1 –C 6 )alkyl-carbonyloxy, phenyl, phenyl-(C 1 –C 6 )alkoxy, phenyl-(C 1 –C 6 )alkoxy-carbonyl, phenoxy, phenoxy-(C 1 –C 6 )alkoxy, phenoxy-(C 1 –C 6 )alkoxy-carbonyl, phenoxycarbonyl, phenylcarbonyloxy and phenyl-(C 1 –C 6 )alkyl-carbonyloxy,

wherein the 9 last-mentioned radicals are unsubstituted or substituted in the phenyl ring by one or more radicals selected from the group consisting of halogen, (C 1 –C 4 )alkyl, (C 1 –C 4 )alkoxy, (C 1 –C 4 )haloalkyl, (C 1 –C 4 )haloalkoxy and nitro,

and radicals of the formula —O—N═CR′ 2 , —N═CR′ 2 ,

wherein the R′ in the formulae independently of one another are hydrogen, (C 1 –C 4 )alkyl or phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 –C 4 )alkyl, (C 1 –C 4 )alkoxy, (C 1 –C 4 )haloalkyl, (C 1 –C 4 )haloalkoxy and nitro, or together are a (C 2 –C 6 )alkylene chain.

3. The combination claimed in claim 2 wherein in formula (I)

R 1 and R 2 both are phenyl and R 3 is hydrogen or (C 1 –C 6 )alkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of

halogen, cyano, (C 1 –C 4 )alkoxy, (C 2 –C 4 )alkenyloxy, (C 2 –C 4 )alkinyloxy, (C 1 –C 4 )haloalkoxy, (C 2 –C 4 )alkylthio, (C 3 –C 6 )cycloalkyl, (C 3 –C 6 )cycloalkoxy, (C 1 –C 4 )alkoxy-carbonyl, (C 2 –C 4 )alkenyloxy-carbonyl, (C 2 –C 4 )alkinyloxy-carbonyl, (C 1 –C 4 )alkyl-carbonyl, (C 1 –C 4 )alkyl-carbonyloxy, phenyl which is unsubstituted or substituted in the phenyl ring by one or more radicals selected from the group consisting of halogen, (C 1 –C 4 )alkyl, (C 1 –C 4 )alkoxy, (C 1 –C 4 )haloalkyl and (C 1 –C 4 )haloalkoxy.

4. The combination as claimed in to claim 3 wherein in formula (I)

R 3 is H or (C 1 –C 4 )alkyl.

5. The combination as claimed in claim 1 wherein the safener of formula (I) is 5,5-diphenyl-2-isoxazoline-3-carboxylic acid.

6. The combination as claimed in claim 5 , wherein the herbicide is selected from the group consisting of:

(B1-1) florasulam;

(B1-2) cloransulam;

combination of (B2-1) dicamba and (B2-2) diflufenzopyr;

(B2-3) triclopyr;

(B2-4) fluroxypyr;

(B3-1) metribuzin;

(B4-1) carfentrazone-methyl;

(B5-1) S-metolachlor;

(B5-2) dimethenamid;

(B5-3) dimethenamid-P;

(B5-4) flufenacet; and

mixtures thereof.

7. A method of combatting weed plants in a crop of useful plants wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 6 .

8. A method of reducing the phytotoxicity of a herbicide B) to a crop plant wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 6 .

9. A method of combatting weed plants in a crop of useful plants wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 5 .

10. A method of reducing the phytotoxicity of a herbicide B) to a crop plant wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 5 .

11. The combination as claimed in claim 1 wherein the safener of formula (I) is ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.

12. The combination as claimed in claim 11 , wherein the herbicide is selected from the group consisting of:

(B1-1) florasulam;

(B1-2) cloransulam;

combination of (B2-1) dicamba and (B2-2) diflufenzopyr;

(B2-3) triclopyr;

(B2-4) fluroxypyr;

(B3-1) metribuzin;

(B4-1) carfentrazone-methyl;

(B5-1) S-metolachlor;

(B5-2) dimethenamid;

(B5-3) dimethenamid-P;

(B5-4) flufenacet; and

mixtures thereof.

13. A method of combatting weed plants in a crop of useful plants wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 12 .

14. A method of reducing the phytotoxicity of a herbicide B) to a crop plant wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 12 .

15. A method of combatting weed plants in a crop of useful plants wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 11 .

16. A method of reducing the phytotoxicity of a herbicide B) to a crop plant wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 11 .

17. The combination as claimed in claim 1 which is a co-formulation additionally containing formulation auxiliaries.

18. The combination as claimed in claim 1 , wherein the herbicide is selected from the group consisting of:

(B1-1) florasulam;

(B1-2) cloransulam;

combination of (B2-1) dicamba and (B2-2) diflufenzopyr;

(B2-3) triclopyr;

(B2-4) fluroxypyr;

(B3-1) metribuzin;

(B4-1) carfentrazone-methyl;

(B5-1) S-metolachlor;

(B5-2) dimethenamid;

(B5-3) dimethenamid-P;

(B5-4) flufenacet; and

mixtures thereof.

19. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is florasulam or chloranulam.

20. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is dicamba.

21. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is a combination of dicamba and diflufenzopyr.

22. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is triclopyr.

23. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is fluroxypyr.

24. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is metribuzin.

25. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is carfentrazone-ethyl.

26. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is S-metolachlor.

27. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is dimethenamide.

28. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is dimethenamide-P.

29. The combination as claimed in claim 1 wherein the safener A) is ethyl-2-isoxazoline-3-carboxylate and the herbicide B) is flufenacet.

30. A method of combatting weed plants in a crop of useful plants wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 1 .

31. A method of reducing the phytotoxicity of a herbicide B) to a crop plant wherein a safener A) is applied to the plants, seed of the plants or the area under cultivation before, simultaneously or after a herbicide A) pre-emergent and/or post-emergent related to the crop and wherein the safener A) and the herbicide B) are as defined in claim 1 .