Insecticidal compositions of 2-cyanobenzene sulfonamide compounds and isomeric forms thereof having improved effect
View Patent ↗The present invention comprises 2-cyanobenzenesulfonic acid amides of the formula (I) and isomeric forms thereof (I-A) and (I-B) wherein R 1 , R 2 , R 3 , R 4 , R 5 and A have the aforesaid meaning for the control of animal pests with the use of penetration enhancers and/or ammonium or phosphonium salts.
1. A composition comprising
at least one insecticidal and/or acaricidal active substance of the 2-cyanobenzene-sulfonamide class of general formula (I) and isomeric forms thereof
in which
A stands for hydrogen, C 1 -C 6 alkyl or C 2 -C 6 alkenyl;
R 1 stands for hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R 2 stands for hydrogen, or stands for C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl or C 1 -C 4 alkoxy, each of which is unsubstituted, partially or completely halogenated and/or optionally bears one, two or three residues selected from the group consisting of C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 alkoxycarbonyl, cyano, amino, (C 1 -C 4 alkyl)amino, di-(C 1 -C 4 alkyl)amino, C 3 -C 8 cycloalkyl and phenyl, wherein the phenyl is unsubstituted, partially or completely halogenated and/or optionally bears one, two or three substituents selected from the qroup consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; and
R 3 , R 4 and R 5 independently stand for hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 alkoxycarbonyl, amino, (C 1 -C 4 alkyl)amino, di-(C 1 -C 4 alkyl)amino, aminocarbonyl, (C 1 -C 4 alkyl)aminocarbonyl or di-(C 1 -C 4 alkyl)aminocarbonyl,
ammonium sulfate;
at least one penetration enhancer, wherein the penetration enhancer is rape oil methyl ester.
2. The composition as claimed in claim 1 , wherein the active substance is a 2-cyanobenzenesulfonamide of the isomeric form (I-A)
in which
R 1 stands for hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R 2 stands for C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl or C 1 -C 4 alkoxy, each of which is unsubstituted, partially or completely halogenated and/or optionally bears one, two or three residues selected from the group consisting of C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 1 -C 4 alkoxycarbonyl, cyano, amino, (C 1 -C 4 alkyl)amino, di-(C 1 -C 4 alkyl)amino, C 3 -C 8 cycloalkyl and phenyl, wherein the phenyl is unsubstituted, partially or completely halogenated and/or optionally bears one, two or three substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkoxy; and
R 3 , R 4 and R 5 independently stand for hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 alkoxycarbonyl, amino, (C 1 -C 4 alkyl)amino, di-(C 1 -C 4 alkyl)amino, aminocarbonyl, (C 1 -C 4 alkyl)aminocarbonyl or di-(C 1 -C 4 alkyl)aminocarbonyl.
3. The composition as claimed in claim 1 , wherein the active substance is between 0.5 and 50% by weight.
4. The composition as claimed in claim 1 , wherein said composition comprises between 0.5 and 80 mmol/l of ammonium sulfate.
5. The composition as claimed in claim 1 , wherein the content of penetration enhancer is between 1 and 95% by weight.
6. A method for controlling noxious insects and/pr spider mites, comprising applying an effective amount of a composition as claimed in claim 1 , either undiluted or diluted, onto said insects and/or spider mites or their habitat.
7. A method for increasing the action of pesticides containing an active substance of the 2-cyanobenzenesulfonamide class of general formula (I) and/or isomeric form (I-A) as claimed in claim 1 or claim 2 , comprising preparing a ready-to-use spray comprising said pesticides, ammonium sulfate, and at least said one penetration enhancer that is rape oil methyl ester.
8. The method as claimed in claim 7 , wherein the penetration enhancer is present in a final concentration of 0.1 to 10 g/l and/or the ammonium sulfate is present in a final concentration of 0.5 to 80 mmol/l.
9. The composition of claim 1 , wherein said 2-cyanobenzene-sulfonamide has the formula:
10. The composition of claim 9 , wherein the penetration enhancer is present in a final concentration of 0.1 to 10 g/l and ammonium sulfate is present in a final concentration of 0.5 to 80 mmol/l.
11. The composition of claim 9 , wherein said 2-cyanobenzene-sulfonamide is present in a concentration of 0.1 to 50 wt %.