Insecticidal triffluormethyl alkane derivatives

Abstract

There are provided new alkane and alkoxyalkane derivatives of the general formula Iin which R1, R2, R3, R4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.

We claim:  
     
       1. An alkane or alkoxyalkane  derivative of the formula                    
       in which 
       R 1  is aryl or heteroaryl or these groups substituted by C 1-4  alkyl, halo-C 1-4  alkyl, phenyl-C 1-4  alkyl, C 2-4  alkenyl, halo-C 2-4  alkenyl, phenyl-C 2-4  alkenyl, C 2-4  alkynyl, halo-C 2-4  alkynyl, phenyl-C 2-4  alkynyl, C 1-4  alkoxy, halo-C 1-4  alkoxy, phenyl-C 1-4  alkoxy, C 2-4  alkenyloxy, halo-C 2-4  alkenyloxy, phenyl-C 2-4  alkenyloxy, C 2-4  alkynyloxy, halo-C 2-4  akynyloxy, phenyl-C 2-4  alkynyloxy, alkylsulphonyloxy, haloalkylsulphonyloxy, arylsulphonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C 1-4  alkylaryloxy, or nitroaryloxy, wherein heteroaryl is benzofuranyl, benzothiophenyl, benzoxazolyl, indanyl or benzodioxanyl  
       R 2  is hydrogen or C 1-4  alkyl,  
       R 3  is hydrogen, cyano or ethynyl,  
       R 4  is phenyl or pyridyl or these groups substituted by at least one of C 1-6  alkyl, halo-C 1-6  alkyl, phenyl-C 1-6  alkyl, C 2-6  alkyl interrupted by an O-, N- or S-atom, C 2-4  alkenyl, halo-C 2-4  alkenyl, phenyl-C 2-4  alkenyl, C 1-4  alkoxy, halo-C 1-4  alkoxy, phenyl-C 1-4  alkoxy, C 2-4  alkenyloxy, halo-C 2-4  alkenyloxy, phenyl-C 2-4  alkenyloxy, C 2-4  alkynyloxy, halo-C 2-4  alkynyloxy, phenyl-C 2-4  alkynyloxy, aryloxy, haloaryloxy, C 1-4  alkylaryloxy, arylamino, haloarylamino, C 1-4  alkylarylamino, aryl-N-C 1-4  alkylamino, aryl-N-C 1-4  acylamino, aroyl, haloaroyl, C 1-4  alkylaroyl, aryl, haloaryl, C 1-4  alkylaryl or halo, and  
       A is CH 2  or O .  
     
     
       2. Alkane or alkoxyalkane  derivative according to claim  1 , in which 
       R 1  is chlorophenyl, bromophenyl, fluorophenyl, methylphenyl, methoxyphenyl, ethoxyphenyl, difluoromethoxyphenyl, fluoroethoxyphenyl, or trifluoroethoxyphenyl,  
       R 2  is hydrogen or methyl,  
       R 3  is hydrogen,  
       R 4  is phenoxyphenyl, fluorophenoxyphenyl or phenoxypyridyl and  
       A is CH 2  or O .  
     
     
       3. Insecticidal and acaricidal composition which comprises a compound claimed in claim  1  in admixture with an agriculturally acceptable diluent. 
     
     
       4. A method of combating insects and acarids which comprises applying to the insects or acarids or their locus an effective amount of a compound claimed in claim  1 . 
     
     
       5. The method of claim  4  in which said compound is [2-(4-ethoxyphenyl)-2-trifluoromethylpropyl](4-fluoro-3-phenoxybenzyl)ether, 2-phenoxybenzyl 2-phenyl-2-trifluoromethylethyl ether or 4-fluoro-3-phenoxybenzyl 2-(4-methoxyphenyl)-2-trifluoromethylpropyl ether. 
     
     
       6. The method of claim  4  in which said compound is 5-(4-fluoro-3-phenoxyphenyl)-2-(4-methoxyphenyl)-2-trifluoromethylpentane, 4-(3-phenoxyphenyl)-1-phenyl-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-methoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-isopropoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(6-phenoxy-2-pyridyl)-1-trifluoromethylbutane, 4-(3-phenoxyphenyl)-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane, or [4-(4-fluoro-3-phenoxy)phenyl]-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane. 
     
     
       7. A method of combatting insects and acarids which comprises applying to the insects or acarids or to their locus an effective amount of a compound claimed in claim  2 . 
     
     
       8. Insecticidal and acaricidal composition according to claim  3  in which said compound is [2-(4-ethoxyphenyl)-2-trifluoromethylpropyl](4-fluoro-3-phenoxybenzyl)ether, 2-phenoxybenzyl 2-phenyl-2-trifluoromethylethyl ether or 4-fluoro-3-phenoxybenzyl 2-(4-methoxyphenyl)-2-trifluoromethylpropyl ether. 
     
     
       9. Insecticidal and acaricidal composition according to claim  3  in which said compound is 5-(4-fluoro-3-phenoxyphenyl)-2-(4-methoxyphenyl)-2-trifluoromethylpentane, 4-(3-phenoxyphenyl)-1-phenyl-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-methoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-isopropoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(6-phenoxy-2-pyridyl)-1-trifluoromethylbutane, 4-(3-phenoxyphenyl)-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane, or [4-(4-fluoro-3-phenoxy)phenyl]-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane. 
     
     
       10. Insecticidal and acaricidal composition which comprises a compound claimed in claim  2  in admixture with an agriculturally acceptable diluent. 
     
     
       11. Alkane or alkoxyalkane derivative according to claim  1  which is [2-(4-ethoxyphenyl)-2-trifluoromethylpropyl](4-fluoro-3-phenoxybenzyl)ether, 2-phenoxybenzyl 2-phenyl-2-trifluoromethylethyl ether or 4-fluoro-3-phenoxybenzyl 2-(4-methoxyphenyl)-2-trifluoromethylpropyl ether. 
     
     
       12. Alkane or alkoxyalkane  derivative according to claim  1  which is 5-(4-fluoro-3-phenoxyphenyl)-2-(4-methoxyphenyl)-2-trifluoromethylpentane, 4-(3-phenoxyphenyl)-1-phenyl-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-methoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(3-fluoro-4-isopropoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1-trifluoromethylbutane, 1-(4-ethoxyphenyl)-4-(6-phenoxy-2-pyridyl)-1-trifluoromethylbutane, 4-(3-phenoxyphenyl)-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane, and [4-(4-fluoro-3-phenoxy)phenyl]-1-trifluoromethyl-1-(3-trifluoromethylphenyl)butane. 
     
     
       13. Alkane derivative according to claim  1  which is  1 -(   4   - ethoxyphenyl )-   4   -(   4   - fluoro -   3   - phenoxyphenyl )-   1   - trifluoromethylbutane or  1   -(   4   - ethoxy -   3   - fluorophenyl )-   4   -(   3   - phenoxyphenyl )-   1   - trifluoromethylbutane.    
     
     
       14. Insecticidal and acaricidal composition which comprises a compound claimed in claim  13  in admixture with an agriculturally acceptable diluent.  
     
     
       15. A method of combating insects and acarids which comprises apply to the insects or acarids or their locus an effective amount of a compound claimed in claim  13 .