Imino ethers useful for controlling insect and arachnoid pests

A compound selected from the group consisting of:

• Methyl 2-chloro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboximida te,
• Ethyl 2-chloro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboximida te,
• Ethyl 2,6-difluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboxi midate,
• Ethyl 2-fluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboximida te,
• Methyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Methyl 2-trifluoromethyl-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzeneca rboximidate,
• Methyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate,
• Methyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate,
• Methyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Methyl 2,6-difluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboxi midate,
• Methyl 2,6-difluoro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Methyl 2,6-difluoro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate,
• Methyl 2,6-dimethoxy-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benz enecarboximidate,
• Methyl 2,6-dichloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Methyl 2,6-dichloro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate,
• Methyl 2-chloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate,
• Methyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate,
• Methyl 2-chloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate,
• Methyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethylthio)phenyl]amino]carbonyl] benzenecarboximidate,
• Methyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate,
• Methyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate,
• Methyl 2,6-dibromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzen ecarboximidate,
• Methyl 2-bromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzenecar boximidate,
• Methyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]carbon yl]benzenecarboximidate,
• Methyl 2-fluoro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate,
• Methyl 2-trifluoromethyl-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylami no]carbonyl]benzenecarboximidate,
• Methyl 2,6-difluoro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Methyl 2,6-dichloro-N-[[[3-(2,2-dichloro-1,1-d ifluoroethoxy)phenyl]amino]carbonyl]benzenecarboximidate,
• Ethyl 2-trifluoromethyl-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Methyl 2,6-difluoro-N-[[[4-(1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl]b enzenecarboximidate,
• Methyl 2,6-dichloro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate,
• Ethyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Ethyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate,
• Ethyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate,
• Ethyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate.
• Ethyl 2,6-difluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboxi midate,
• Ethyl 2,6-difluoro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Ethyl 2,6-difluoro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate,
• Ethyl 2,6-dimethoxy-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benz enecarboximidate,
• Ethyl 2,6-dichloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Ethyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]carb onyl]benzenecarboximidate,
• Ethyl 2-chloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate,
• Ethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate,
• Ethyl 2-chloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate,
• Ethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethylthio)phenyl]amino]carbonyl] benzenecarboximidate,
• Ethyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate,
• Ethyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate,
• Ethyl 2,6-dibromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzen ecarboximidate,
• Ethyl 2-bromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzenecar boximidate,
• Ethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]carbon yl]benzenecarboximidate,
• Ethyl 2-fluoro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate,
• Ethyl 2-trifluoromethyl-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylami no]carbonyl]benzenecarboximidate,
• Ethyl 2,6-difluoro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Ethyl 2,6-dichloro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• Ethyl 2,6-difluoro-N-[[[4-(1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl]b enzenecarboximidate,
• Ethyl 2,6-dichloro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate,
• 1-Methylethyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• 1-Methylethyl 2-trifluoromethyl-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzeneca rboximidate,
• 1-Methylethyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate,
• 1-Methylethyl 2,6-dichloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benze necarboximidate,
• 1-Methylethyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• 1-Methylethyl 2,6-difluoro-N-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]benzenecarboxi midate,
• 1-Methylethyl 2,6-difluoro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• 1-Methylethyl 2,6-difluoro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate,
• 1-Methylethyl 2,6-dimethoxy-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benz enecarboximidate,
• 1-Methylethyl 2,6-dichloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• 1-Methylethyl 2,6-dichloro-N-[[[4-((2,2-dichloro-1,1-difluoroethyl)thio)phenyl]amino]car bonyl]benzenecarboximidate,
• 1-Methylethyl 2-chloro-N-[[[2-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate,
• 1-Methylethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl]ben zenecarboximidate,
• 1-Methylethyl 2-chloro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate,
• 1-Methylethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethylthio)phenyl]amino]carbonyl] benzenecarboximidate,
• 1-Methylethyl 2,6-dichloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate,
• 1-Methylethyl 2,6-difluoro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]ca rbonyl]benzenecarboximidate,
• 1-Methylethyl 2,6-dibromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzen ecarboximidate,
• 1-Methylethyl 2-bromo-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzenecar boximidate,
• 1-Methylethyl 2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylamino]carbon yl]benzenecarboximidate,
• 1-Methylethyl 2-fluoro-N-[[[4-(1,1,2,2-tetrafluoroethoxy)phenyl]amino]carbonyl]benzeneca rboximidate,
• 1-Methylethyl 2-trifluoromethyl-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)phenyl]methylami no]carbonyl]benzenecarboximidate,
• 1-Methylethyl 2,6-difluoro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• 1-Methylethyl 2,6-dichloro-N-[[[3-(2,2-dichloro-1,1-difluoroethoxy)phenyl]amino]carbonyl ]benzenecarboximidate,
• 1-Methylethyl 2,6-difluoro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate,
• 1-Methylethyl 2,6-dichloro-N-[[[4-((1,1,2,2-tetrafluoroethyl)thio)phenyl]amino]carbonyl] benzenecarboximidate.

A method for controlling insect pests which comprises contacting susceptible insect pests with an effective amount of a compound of the formula:

• ##STR3## wherein X.sub.1 and X.sub.2 are the same or different and are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, methoxy and trifluoromethyl;
• R is alkyl of from 1 to 5 carbon atoms;
• Y is selected from oxygen or sulfur;
• and R.sub.1 is selected from a halo(C.sub.1 -C.sub.3)alkyl.

Formulations useful for controlling susceptible insect and arachnoid pests comprising an adjuvant carrier and as active ingredient a biologically effective amount of one or more compounds of the formula:

• ##STR4## wherein X.sub.1 and X.sub.2 are the same or different and are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, methyl, methoxy and trifluoromethyl;
• R is alkyl of from 1 to 5 carbon atoms;
• Y is selected from the oxygen or sulfur;
• and R.sub.1 is a halo(C.sub.1 -C.sub.3)alkyl.