Claims
- 1. A quaternary ammonium salt of sulfonylurea having the formula wherein R1 is a substituted or unsubstituted phenyl, heterocyclic ring, or phenoxy, or —N(CH3)(SO2CH3); R2 is H or CH3; R3 is a substituted or unsubstituted pyrimidine or a substituted or unsubstituted triazine; R4 and R5 are independently unsubstituted or hydroxy substituted linear or branched C1-C4 alkyls, —(CH2CH2O)mCH2CH2OH, or —(CH2CHCH3O)mCH2CHCH3OH where m is 1 to 10; R6 is a benzyl, ethylbenzyl, naphthylmethyl, or linear or branched C1-C22 alkyl; R7 is —R13(O)n(C6H5)R14 where n is 0 or 1; R13 is a C1-C8 alkyl or C1-C8 alkoxyalkyl; and R14 is a linear or branched C1-C12 alkyl.
- 2. The compound of claim 1, wherein R1 is R8 is CON(CH3)2, SO2R11, or CO2R12; and R11 and R12 are independently C1-C3 alkyls.
- 3. The compound of claim 2, wherein R1 is selected from the group consisting of 3-(dimethylamino)carbonyl-2-pyridinyl, 3-(ethylsulfonyl)-2-pyridinyl, 2-carbomethoxyphenyl, and 2-carbomethoxythienyl.
- 4. The compound of claim 1, wherein R3 is R9 is CH3, OCH3, OCH2CH3, or NHCH3; Y is CH or N; and R10 is CH3 or OCH3.
- 5. The compound of claim 4, wherein R3 is selected from the group consisting of 4,6-dimethoxy-2-pyrimidinyl and 4-methoxy-6-methyl-1,3,5-triazin-2-yl.
- 6. The compound of claim 1, wherein said sulfonylurea is selected from the group consisting of 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]suflonyl]-N,N-dimethyl-3-pyridinecarboxamide, N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-(ethylsulfonyl)-2-pyridinesulfonamide, methyl 2-[[[[(4-methoxy-6-methyl)-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoate, methyl ester of 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]sulfonyl]benzoic acid, 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-2-thiophenecarboxylic, 2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide, methyl 2-[[[[(4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]benzoate, methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate, ethyl 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate, methyl 2-[[[[(4,6-dimethyl-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoate, and N-[[(4,6-dimethoxypyrimidine-2-yl)amino]carbonyl]-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide.
- 7. The compound of claim 1, wherein said sulfonylurea is selected from the group consisting of nicosulfuron, rimsulfuron, metsulfuron-methyl, tribenuron-methyl, trifensulfuron-methyl, chlorsulfuron, ethametsulfuron methyl, triflusulfuron methyl, chlorimuron ethyl, sulfometuron methyl, bensulfuron methyl, azimsulfuron, flupyrsulfuron methyl, amidosulfuron, iodosulfuron, ethoxysulfuron, prosulfuron, oxasulfuron, primisulfuron, triasulfuron, cinosulfuron, flazasulfuron, halosulfuron, and imazosulfuron.
- 8. The compound of claim 1, wherein R13 is —CH2CH2OCH2CH2—.
- 9. The compound of claim 1, wherein R7 is [2-[2-(4-diisobutylphenoxy)ethoxy]ethyl].
- 10. The compound of claim 1, wherein said quaternary ammonium is selected from the group consisting of dialkyl (C8 to C22) dimethylammonium, dialkyl (C8 to C22) methyl poly(oxyethyl) ammonium, alkyl (C8 to C22) benzyldimethyl ammonium, alkyl (C8 to C22) trimethylammonium, dialkyl (C8 to C22) dihydroxyethyl ammonium, dialkyl (C8 to C22) methyl hydroxyethyl ammonium, and alkyl (C8 to C22) methyl dihydroxyethyl ammonium.
- 11. The compound of claim 1, wherein said quaternary ammonium is selected from the group consisting of [2-[2-(4-diisobutylphenoxy)ethoxy]ethyl] dimethylbenzyl ammonium, N,N-didecyldimethylammonium, N,N-dioctyldimethyl ammonium, N,N-octyldecyldimethyl ammonium, octadecyldimethylbenzylammonium, N,N-decylisononyldimethyl ammonium, hexadecyltrimethylammonium, N,N-didecyl-N-methyl-poly(oxyethyl)ammonium, alkyl (C10-C18) dimethylbenzylammonium, and didecylmethylhydroxyethyl ammonium.
- 12. A method of preparing a quaternary ammonium salt of sulfonylurea comprising contacting a quaternary ammonium hydroxide with a sulfonylurea to form said quaternary ammonium salt of sulfonylurea, wherein the quaternary ammonium hydroxide has the formula R4 and R5 are independently unsubstituted or hydroxy substituted linear or branched C1-C4 alkyls, —(CH2CH2O)mCH2CH2OH or —(CH2CHCH3O)mCH2CHCH3OH where m is 1 to 10; R6 is a benzyl, ethylbenzyl, naphthylmethyl, or linear or branched C1-C22 alkyl; R7 is —R13(O)n(C6H4)R14 where n is 0 or 1; R13 is a C1-C8 alkyl or C1-C8 alkoxyalkyl; and R14 is a linear or branched C1-C12 alkyl.
- 13. The method of claim 12, wherein said sulfonylurea has the formula wherein R1 is a substituted or unsubstituted phenyl, heterocyclic ring, or phenoxy, or —N(CH3)(SO2CH3); R2 is H or CH3; R3 is a substituted or unsubstituted pyrimidine or a substituted or unsubstituted triazine.
- 14. The method of claim 13, wherein R1 is R8 is CON(CH3)2, SO2R11, or CO2R12; and R11 and R12 are independently C1-C3 alkyls.
- 15. The method of claim 13, wherein R1 is selected from the group consisting of 3-(dimethylamino)carbonyl-2-pyridinyl, 3-(ethylsulfonyl)-2-pyridinyl, 2-carbomethoxyphenyl, and 2-carbomethoxythiophenyl.
- 16. The method of claim 13, wherein R3 is R9 is CH3, OCH3, OCH2CH3, or NHCH3; Y is CH or N; and R10 is CH3 or OCH3.
- 17. The method of claim 13, wherein R3 is selected from the group consisting of 4,6-dimethoxy-2-pyrimidinyl and 4-methoxy-6-methyl-1,3,5-triazin-2-yl.
- 18. A pesticidal, herbicidal, fungicidal, or plant growth regulating agent composition comprising an effective amount of one or more compounds of claim 1.
- 19. A method of controlling plants or fungi or regulating the growth of plants comprising applying an effective amount of one or more compounds of claim 1 to the plants or fungi, the seeds of the plants, or the area on which the plants or fungi grow.
Parent Case Info
This application is a continuation-in-part of U.S. Ser. No. 60/117,222, filed Jan. 25, 1999, and PCT Application Serial No. PCT/US97/21383, filed Nov. 19, 1997, which claims priority from U.S. Ser. No. 60/032,019, filed Nov. 22, 1996.
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4479821 |
Meyer et al. |
Oct 1984 |
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4681619 |
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Provisional Applications (2)
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Number |
Date |
Country |
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60/117222 |
Jan 1999 |
US |
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60/032019 |
Nov 1996 |
US |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
PCT/US97/21383 |
Nov 1997 |
US |
Child |
09/315391 |
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US |