Combinations of phenylsulfonylurea herbicides and safeners
View Patent ↗The invention relates to combinations of sulfonylurea herbicides (A) and their salts in which R 2 is H, OH, aliphatic hydrocarbon radical or hydrocarbon-oxy radical, and R 1 is an acyl radical, and the other symbols are as defined in claim 1, and safeners of type (B1) and (B2) in which the symbols are as defined in claim 1.
1. A herbicide/safener combination comprising:
(A) at least one herbicidal active substance selected from the group consisting of:
mesosulfuron-methyl;
(A5) N-(4,6-Dimethoxypyrimidin-2-ylaminocarbonyl)-2-methoxycarbonyl-5-(N-isopropionylmethylamino)benzenesulfonamide sodium salt;
(A6) N-(4,6-Dimethoxypyrimidin-2-ylaminocarbonyl)-2-methoxycarbonyl-5-(N-methoxycarbonylaminomethyl)benzenesulfonamide sodium salt
(A7) N-(4,6-Dimethoxypyrimidin-2-ylaminocarbonyl)-2-(N,N-dimethylaminocarbonyl)-5-(N-methoxycarbonylamino)benzene sulfonamide sodium salt
(A8) N-(4,6-Dimethoxypyrimidn-2-ylaminocarbonyl)-2-(N,N-dimethylaminocarbonyl)-5-(N-formylamino)benzenesulfonamide;
(A10) N-(4,6-Dimethoxypyrimidin-2-ylaminocarbonyl)-2-(methoxycarbonyl)-5-(N-methylsulfonylaminomethyl)benzenesulfonamide sodium salt;
(A11) N -(4,6-Dimethoxypyrimidin-2-ylaminocarbonyl)-2-(methoxycarbonyl)-5-(N-methoxycarbonylaminomethyl)benzenesulfonamide sodium salt;
(A12) N-(4,6-Dixnethoxypyrimidin-2-ylaminocarbonyl)-2-(methoxycarbonyl)-5-(N-methylsulfonyl-N-methylaminomethyl)benzenesulfonamide;
(A13) N-(4,6-Dimethoxypyrimidin-2-ylaminocarbonyl)-2-(N,N-dimethylaminocarbonyl)-5-(N-methoxycarbonylamino)benzenesulfonamide; and
(B) at least one safener;
wherein, when the herbicidal active substance is mesosulfuron-methyl, the safener is:
cloquintocet-mexyl;
wherein, when the herbicidal active substance is (A5), the safener is selected from the group consisting of:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate; and
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate;
wherein, when the herbicidal active substance is (A6), the safener is selected from the group consisting of:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate;
(B1-6) Ethyl 1-(2,4-dichlorophenyl)-5-(trichlbromethyl(1H)-1,2,4-triazole-3- carboxylate; and
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate;
wherein, when the herbicidal active substance is (A7), the safener is selected from the group consisting of:
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate;
(B1-10) n-Propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate; and
(B1-11) Ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate;
wherein, when the herbicidal active substance is (A8), the safener is selected from the group consisting of
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate; and
(B1-11) Ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate;
wherein, when the herbicidal active substance is (A10), the safener is:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate;
wherein, when the herbicidal active substance is (A11), the safener is selected from the group consisting of:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate; and
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate;
wherein, when the herbicidal active substance is (A12), the safener is:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate;
wherein, when the herbicidal active substance is (A13), the safener is:
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate; and
wherein the herbicide/safener combination has an increased herbicidal activity compared to the herbicidal active substance alone.
2. The herbicide/safener combination as claimed in claim 1 ;
wherein the combination is formulated in the form of a composition (herbicidal composition), and contains:
0.1 to 95% by weight of active substances (A) and (B); and
1 to 99.9% by weight of customary formulating agents.
3. The herbicide/safener combination as claimed in 1 ;
wherein the active substances (A) and (B) are present in the ratio of from 1:100 to 100:1 by weight.
4. A method for protecting crop plants from phytotoxic side effects of herbicide (A), comprising:
applying an effective amount of safener (B) before, after, or at the same time as herbicide (A) to the plants, plant parts, plant seeds, or the growing area;
wherein the combination of herbicide (A) and safener (B) is as defined in claim 1 .
5. The method as claimed in claim 4 ;
wherein the crop plants are cereal plants, rice plants, or corn plants.
6. The method as claimed in claim 4 ;
wherein the herbicide (A) is applied at an application rate of 0.001 to 10 kg/ha active substance; and
wherein a safener:herbicide ratio by weight is from 1:100 to 100:1.
7. The herbicide/safener combination as claimed in claim 1 ;
wherein the herbicidal active substance is mesosulfuron-methyl, and the safener is cloquintocet-mexyl.
8. The herbicide/safener combination as claimed in claim 1 ;
wherein the herbicidal active substance is (A5), and the safener is selected from the group consisting of:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate; and
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.
9. The herbicide/safener combination as claimed in claim 1 ;
wherein the herbicidal active substance is (A6), and the safener is selected from the group consisting of:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate;
(B1-6) Ethyl 1-(2,4-dichlorophenyl)-5-(trichlbromethyl(1H)-1,2,4-triazole-3-carboxylate; and
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.
10. The herbicide/safener combination as claimed in claim 1 ;
wherein the herbicidal active substance is (A7), and the safener is selected from the group consisting of:
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate;
(B1-10) n-Propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate; and
(B1-11) Ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate.
11. The herbicide/safener combination as claimed in claim 1 ;
wherein, the herbicidal active substance is (A8), and the safener is selected from the group consisting of:
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate; and
(B1-11) Ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate.
12. The herbicide/safener combination as claimed in claim 1 ;
wherein the herbicidal active substance is (A10), and the safener is:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate.
13. The herbicide/safener combination as claimed in claim 1 ;
wherein, when the herbicidal active substance is (A11), and the safener is selected from the group consisting of:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate; and
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.
14. The herbicide/safener combination as claimed in claim 1 ;
wherein, when the herbicidal active substance is (A12), the safener is:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate.
15. The herbicide/safener combination as claimed in claim 1 ;
wherein, when the herbicidal active substance is (A13), the safener is:
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.
16. The method as claimed in claim 4 ;
wherein the herbicidal active substance is mesosulfuron-methyl, the safener is cloquintocet-mexyl.
17. The method as claimed in claim 4 ;
wherein the herbicidal active substance is (A5), and the safener is selected from the group consisting of:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate; and
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.
18. The method as claimed in claim 4 ;
wherein the herbicidal active substance is (A6), and the safener is selected from the group consisting of:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate;
(B1-6) Ethyl 1-(2,4-dichlorophenyl)-5-(trichlbromethyl(1H)-1,2,4-triazole-3-carboxylate; and
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.
19. The method as claimed in claim 4 ;
wherein the herbicidal active substance is (A7), and the safener is selected from the group consisting of:
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate;
(B1-10) n-Propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate; and
(B1-11) Ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate.
20. The method as claimed in claim 4 ;
wherein the herbicidal active substance is (A8), and the safener is selected from the group consisting of:
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate; and
(B1-11) Ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate.
21. The method as claimed in claim 4 ;
wherein the herbicidal active substance is (A10), and the safener is:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate.
22. The method as claimed in claim 4 ;
wherein, when the herbicidal active substance is (A11), and the safener is selected from the group consisting of:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate; and
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.
23. The method as claimed in claim 4 ;
wherein, when the herbicidal active substance is (A12), the safener is:
(B1-1) Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate.
24. The method as claimed in claim 4 ;
wherein, when the herbicidal active substance is (A13), the safener is:
(B1-9) Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate.