Phenyl pyrazole thioamides

Abstract

The present invention discloses amides and thioamides substituted in the .alpha. or .beta. position with substituted pyrazoles which are useful as herbicides.

Description

The present invention relates to phenyl pyrazole thioamides, for which the essential material constituting a disclosure thereof is incorporated by reference here from U.S. patent application Ser. No. 686,548, filed May 14, 1976, now U.S. Pat. No. 4,072,498.

Claims

1. A compound of the formula: ##STR1## where R.sub.1 is hydrogen, alkyl of 1 to 7 carbon atoms, inclusive, haloalkyl of 1 to 7 carbon atoms, inclusive, phenyl, benzyl or cycloalkyl of 3 to 6 carbon atoms, inclusive, with the proviso that when R.sub.1 is benzyl or cycloalkyl m = 0; R.sub.2 and R.sub.5 are the same or different and are hydrogen, halogen, alkyl of 1 to 6 carbon atoms, inclusive, haloalkyl of 1 to 6 carbon atoms, inclusive, or phenyl; R.sub.1 and R.sub.2 together with the attached carbon atom can be cycloalkyl of 3 to 6 carbon atoms, inclusive, when m = 0, R.sub.1 is not hydrogen and when m = 1 at least one of R.sub.2 or R.sub.5 is hydrogen; R.sub.3 is hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive, phenyl or benzyl; R.sub.4 is hydrogen or alkyl of from 1 to 6 carbon atoms, inclusive, and R.sub.3 and R.sub.4 can be joined together to form a heterocyclic ring selected from the group consisting of pyrrolidine, or piperidine; A and B are the same or different and are hydrogen, alkyl of from 1 to 6 carbon atoms, inclusive, phenyl, halogen, cyano, haloalkyl of 1 to 6 carbon atoms, inclusive, alkoxy or alkylthio in which the alkyl group is from 1 to 3 carbon atoms, inclusive, or trifluoromethyl and when adjacent can be joined to form a ring of from 5 to 7 carbon atoms, inclusive; where X is halogen, nitro, cyano, acetyl, dimethylcarbamoyl, alkyl, haloalkyl, alkoxy or carboalkoxy in which the alkyl group is from 1 to 3 carbon atoms, inclusive, phenyl, benzyl, 2-phenylethyl and n is 0, 1, or 2or an acid addition salt thereof.

2. A compound according to claim 1 which is N,N,.alpha.,4-tetramethyl-3-phenylpyrazole-1-thioacetamide.

3. A compound according to claim 1 which is .alpha.-(n-butyl)-N,N,4-trimethyl-3-phenylpyrazole-1-thioacetamide.

4. A compound according to claim 1 which is 4-chloro-N,N,.alpha.-trimethyl-3-phenylpyrazole-1-thioacetamide.

5. A compound according to claim 1 which is .alpha.-ethyl-N,N,4-trimethyl-3-phenylpyrazole-1-thioacetamide.

6. A compound according to claim 1 which is N,N-dimethyl-.alpha.,4-dimethyl-3-phenylpyrazole-1-thioactamide.

7. A compound according to claim 1 which is N,N,.alpha.-trimethyl-3-phenylpyrazole-1-thioacetamide.

8. A compound according to claim 1 which is N,N,.alpha.,.alpha.,4-pentamethyl-3-phenylpyrazole-1-thioacetamide.

9. A compound according to claim 1 which is N,N,.alpha.,.alpha.-tetramethyl-3-phenylpyrazole-1-thioacetamide.

10. A compound according to claim 1 which is N,.alpha.,.alpha.,4-tetramethyl-3-phenylpyrazole-1-thioacetamide.

11. A compound according to claim 1 which is 3-(o-chlorophenyl)-N,N,.alpha.-trimethylpyrazole-1-thioacetamide.

12. A compound according to claim 1 which is 3-(o-chlorophenyl)-N,N,.alpha.,.alpha.,4-pentamethylpyrazole-1-thioacetamide.

13. A compound according to claim 1 which is .alpha.,4-dimethyl-3-phenylpyrazole-1-thioacetamide.

14. A compound according to claim 1 which is 3-(o-chlorophenyl)-N,N-diethyl-.alpha.,.alpha.,4-trimethylpyrazole-1-thioacetamide.

15. A compound according to claim 1 which is 3-(o-chlorophenyl)-N,.alpha.,.alpha.,4-tetramethylpyrazole-1-thioacetamide.