USRE32418EExpiredUtility

Substituted(((phenyl)amino)carbonyl)-benzamides

8
Priority: May 13, 1977Filed: Feb 10, 1981Granted: May 12, 1987
Est. expiryMay 13, 1997(expired)· nominal 20-yr term from priority
C07C 275/54A01N 47/34
8
PatentIndex Score
1
Cited by
21
References
35
Claims

Abstract

Novel alkoxy or alkylthio substituted(((phenyl)amino)carbonyl)-benzamides are disclosed. The compounds of the instant invention are useful as insecticides and can be formulated to provide insecticidal compositions.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound selected from the group consisting of 2-chloro-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)-benzamide, 2-trifluoromethyl-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-difluoro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-difluoro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-difluoro-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-dichloro-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-dimethoxy-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-dichloro-N-(((2-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-N-methylbenzamide, 2-chloro-N-(4-(((2,2-dichloro-1,1-difluoroethylthio)phenyl)amino)carbonyl)-benzamide, 2,6-dichloro-N-(((4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl)amino)carbonyl)-benzamide, 2-chloro-N-(((2-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2-chloro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-dibromo-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)carbonyl)-benzamide, 2,6-difluoro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)carbonyl)-benzamide, 2-bromo-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-dichloro-N-(((3-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2-chloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)carbonyl)-benzamide, 2,6-difluoro-N-(((3-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-difluoro-N-(((2-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2-trifluoromethyl-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)carbonyl)-benzamide, 2-fluoro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-difluoro-N-(((4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl)amino)carbonyl)-benzamide, 2,6-difluoro-N-(((4-((1,1,2,2-tetrafluoroethyl)thio)phenyl)amino)carbonyl)-benzamide, 2,6-dichloro-N-(((4-((1,1,2,2-tetrafluoroethyl)thio)phenyl)amino)carbonyl)-benzamide, 2,6-dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide, 2,6-dichloro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl-benzamide and 2-chloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       2. The compound of claim 1 which is 2-Chloro-N-(((4-trifluoromethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       3. The compound of claim 1 which is 2-Trifluoromethyl-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       4. The compound of claim 1 which is 2,6-Dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       5. The compound of claim 1 which is 2,6-Dichloro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       6. The compound of claim 1 which is 2,6-Difluoro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       7. The compound of claim 1 which is 2,6-Difluoro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       8. The compound of claim 1 which is .Badd..[.2,6-Difluoro-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl-benzamide.]. .Iadd.2,6-Difluoro-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)-benzamide.Iaddend.. 
     
     
       9. The compound of claim 1 which is 2,6-Dichloro-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       10. The compound of claim 1 which is 2,6-Dimethoxy-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       11. The compound of claim 1 which is 2,6-Dichloro-N-(((2-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       12. The compound of claim 1 which is 2-Chloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       13. The compound of claim 1 which is 2,6-Dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-N-methylbenzamide. 
     
     
       14. The compound of claim 1 which is 2-Chloro-N-(4-(((2,2-dichloro-1,1-difluoroethylthio)phenyl)amino)carbonyl)-benzamide. 
     
     
       15. The compound of claim 1 which is 2,6-Dichloro-N-(((4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl)amino)carbonyl)-benzamide. 
     
     
       16. The compound of claim 1 which is 2-Chloro-N-(((2-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       17. The compound of claim 1 which is 2-Chloro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       18. The compound of claim 1 which is 2,6-Dibromo-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       19. The compound of claim 1 which is 2,6-Dichloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)carbonyl)-benzamide. 
     
     
       20. The compound of claim 1 which is 2,6-Difluoro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)carbonyl)-benzamide. 
     
     
       21. The compound of claim 1 which is 2-Bromo-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide 
     
     
       22. The compound of claim 1 which is 2,6-Dichloro-N-(((3-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       23. The compound of claim 1 which is 2-Chloro-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)carbonyl)-benzamide. 
     
     
       24. The compound of claim 1 which is 2,6-Difluoro-N-(((3-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       25. The compound of claim 1 which is 2,6-Difluoro-N-(((2-(2,2-dichloro-1,1-difluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       26. The compound of claim 1 which is 2-Trifluoromethyl-N-(((4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)methylamino)carbonyl)-benzamide. 
     
     
       27. The compound of claim 1 which is 2-Fluoro-N-(((4-(1,1,2,2-tetrafluoroethoxy)phenyl)amino)carbonyl)-benzamide. 
     
     
       28. The compound of claim 1 which is 2,6-Difluoro-N-(((4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl)amino)carbonyl)-benzamide. 
     
     
       29. The compound of claim 1 which is 2,6-Difluoro-N-(((4-((1,1,2,2-tetrafluoroethyl)thio)phenyl)amino)carbonyl)-benzamide. 
     
     
       30. The compound of claim 1 which is 2,6-Dichloro-N-(((4-((1,1,2,2-tetrafluoroethyl)thio)phenyl)amino)carbonyl)-benzamide. 
     
     
       31. A composition for the control of insects comprising a suitable adjuvant and an insecticidally-effective amount of a compound of claim 1. .Iadd. 
     
     
       32.  A compound of the formula ##STR14## wherein each X substituent is individually chosen from the group consisting of H, Cl, F, Br, CR' 3  and OCR' 3 , wherein each R' substituent is individually, either R" or H, with R" being selected from the group consisting of F, Cl and Br, with the proviso that both X substituents are not H; each A substituent is individually chosen from the group consisting of CH 3  and H, with the proviso that both A substituents are not CH 3  ;   Y represents O; and   R represents a halogenated alkyl group having up to 3 carbon atoms; with the further proviso that when one of the X substituents is Cl the other X substituent is other than F..Iaddend. .Iadd.   
     
     
       33.  An N-phenyl-N'-benzoylurea of the formula ##STR15## in which R represents halogenoalkyl with 1 to 3 carbon atoms; R 2  represents chlorine, bromine, fluorine, methyl or methoxy, with the proviso that each R 2  substituent must be in the ortho position, and the further proviso that when n is 2 and one of the R 2  substituents is chlorine the other R 2  substituent is other than fluorine;   X represents an oxygen atom; and   n denotes 1 or 2..Iaddend. .Iadd.   
     
     
       34.  A urea according to claim 33, in which R represents straight-chain or branched halogenoalkyl with 1 to 3 carbon atoms; R 2  represents fluorine, chlorine, bromine, methyl or methoxy; and n represents 1 or 2..Iaddend. .Iadd.   
     
     
       35.  An insecticidal composition containing as active ingredient an insecticidally effective amount of a compound according to claim 33 in admixture with an agriculturally acceptable diluent..Iaddend.

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