Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides

• US 6,506,784 B1
• Filed: 06/29/2000
• Issued: 01/14/2003
• Est. Priority Date: 07/01/1999
• Status: Expired due to Fees

• Current Assignee: 3-Dimensional Pharmaceuticals, Inc. (Johnson & Johnson), Heska Corporation (Mars Incorporated)
• Original Assignee: 3-Dimensional Pharmaceuticals, Inc. (Johnson & Johnson), Heska Corporation (Mars Incorporated)
• Inventors: Doller, Dario, Meegalla, Sanath, Wisnewski, Nancy, Silver, Gary M., Agrafiotis, Dimitris, Seward, R. Lee, Stinchcomb, Dan T., Soll, Richard M., Dhanoa, Daljit S.
• Primary Examiner(s): Ramsuer, Robert W.
• Application Number:
  US09/606,986
• Time in Patent Office: 929 Days
• Field of Search: 514/407
• US Class Current: 514/407
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles

Abstract

The present invention is directed to inhibiting pest GABA receptors by contacting said receptors with a compound of Formula I:

The invention is also directed to methods of controlling pests, especially insects and arachnids such as fleas and ticks, and to novel compounds within the scope of Formula I.

Claims

1. A method of inhibiting a pest GABA receptor, comprising contacting one or more pest GABA receptors with one or more compounds of Formula I:

or a salt thereof, wherein;

R¹ is C_1-6 alkyl or phenyl, either of which is optionally substituted with one or more of groups independently selected from the group consisting of halogen, hydroxy, methoxy and ethoxy;

R³ is C_1-4 alkyl, C_1-4 alkoxy, C_1-4 alkylthio, C_1-4 alkylsulfinyl or C₁₄ alkylsulfonyl, any of which is optionally substituted by one or more halogen atoms;

R⁴ is hydrogen; and

R⁵ is C_1-8 alkyl, C_3-7 cycloalkyl, C_3-7 cycloalkyl(C_1-4)alkyl, or C_6-14 aryl, any of which is optionally substituted by one to five substituents independently selected from the group consisting of C_1-4 alkyl, C_1-4 alkoxy, C_1-4 alkylthio, hydroxy, amino, halo, and trifluoromethyl.

3. The method of claim 1, wherein R¹ is methyl, ethyl, 2,4,6-trichlorophenyl, 2-6-dichloro-4-difluoromethoxyphenyl, 2-chloro-4-trifluoromethylphenyl, 2-bromo-4,6-di(trifluoromethyl)phenyl, 2,6-dibromo-4-trifluoromethylphenyl or 2-bromo-4-trifluoromethylphenyl.

4. The method of claim 1, wherein R¹ is methyl.

5. The method of claim 1, wherein R³ is trifluoromethyl, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl ethylsulfonyl, propylthio, —

SCH₂CF₃, trifluoromethylthio or trifluoromethylsulfonyl.

6. The method of claim 1, wherein R⁵ is methyl, ethyl, propyl, butyl, pentyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, 2,4,6-trichlorophenyl, 2-6-dichloro-4-difluoromethoxyphenyl, 2-chloro-4-trifluoromethylphenyl, 2-chloro-4-fluorophenyl, 2,4-dichlorophenyl, 2-bromo-4,6-di(trifluoromethyl)phenyl, 2,6-dibromo-4-trifluoromethylphenyl or 2-bromo-4-trifluoromethylphenyl.

7. The method of claim 1, wherein R⁵ is 2-chloro-4-trifluoromethylphenyl, 2-chloro-4-fluorophenyl, or 2,4-dichlorophenyl.

8. The method of claim 1, wherein R¹ is methyl, R³ is trifluoromethyl, R⁴ is hydrogen and R⁵ is 2-chloro-4-trifluoromethylphenyl, 2-chloro-4-fluorophenyl, or 2,4-dichlorophenyl.

11. The method of claim 1, wherein R¹ is C_1-6 optionally substituted alkyl;

R³ is C_1-4 alkyl optionally substituted by one or more halogens;

R⁴ is hydrogen; and

R⁵ is optionally substituted C_6-14 aryl.

2. A method for controlling pests, comprising contacting a vertebrate animal, plant or inanimate object with a pesticidally effective amount of at least one compound of Formula I:

or a salt thereof, wherein

R¹ is C_1-6 alkyl or phenyl, either of which is optionally substituted with one or more groups independently selected from the group consisting of halogen, hydroxy, methoxy and ethoxy;

R³ is C_1-4 alkyl, C_1-4 alkoxy, C_1-4 alkylthio, C_1-4 alkylsulfinyl or C_1-4 alkylsulfonyl, any of which is optionally substituted by one or more halogen atoms;

R⁴ is hydrogen; and

R⁵ is C_1-8 alkyl, C_3-7 cycloalkyl, C_3-7 cycloalkyl(C_1-4)alkyl, or C_6-14 aryl, any of which is optionally substituted by one to five substituents independently selected from the group consisting of C_1-4 alkyl, C_1-4 alkoxy, C_1-4 alkylthio, hydroxy, amino, halo, and trifluoromethyl.

9. The method of claim 2, wherein R¹ is methyl, R³ is trifluoromethyl, R⁴ is hydrogen and R⁵ is 2-chloro-4-trifluoromethylphenyl, 2-chloro-4-fluorophenyl, or 2,4-dichlorophenyl.

10. The method of claim 2, wherein said pests are insects, arachnids, leeches or any combination thereof.

12. The method of claim 2, wherein R¹ is methyl, ethyl, 2,4,6-trichlorophenyl, 2-6-dichloro-4-difluoromethoxyphenyl, 2-chloro-4-trifluoromethylphenyl, 2-bromo -4,6 -di(trifluoromethyl)phenyl, 2,6-dibromo-4-trifluoromethylphenyl or 2-bromo-4-trifluoromethylphenyl.

13. The method of claim 2, wherein R¹ is methyl.

14. The method of claim 2, wherein R³ is trifluoromethyl, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl ethylsulfonyl, propylthio, —

SCH₂CF₃, trifluoromethylthio or trifluoromethylsulfonyl.

15. The method of claim 2, wherein R⁵ is methyl, ethyl, propyl, butyl, pentyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, 2,4,6-trichlorophenyl, 2-6-dichloro-4-difluoromethoxyphenyl, 2-chloro-4-trifluoromethylphenyl, 2-chloro-4-fluorophenyl, 2,4-dichlorophenyl, 2-bromo-4,6-di(trifluoromethyl)phenyl, 2,6-dibromo-4-trifluoromethylphenyl or 2-bromo-4-trifluoromethylphenyl.

16. The method of claim 2, wherein R⁵ is 2-chloro-4-trifluoromethylphenyl, 2-chloro-4-fluorophenyl, or 2,4-dichlorophenyl.

17. The method of claim 2, wherein R¹ is methyl, R³ is trifluoromethyl, R⁴ is hydrogen and R⁵ is 2-chloro-4-trifluoromethylphenyl, 2-chloro-4-fluorophenyl, or 2,4-dichlorophenyl.