Arylsulfenylated methylcarbamates

Arylsulfenylated methylcarbamates also may have other interesting types of selectivity. An example is given in the honey bee and house fly toxicity data in Table II for several derivatives of propoxur (13). Propoxur and most of the derivatives were highly toxic to the honey bee in fact, compounds 10-15 were substantially more toxic to the honey bee than to the house fly (also see Table I). The order of toxicity, however, was reversed with the 4-jt-butylphenyl analog (16) and the 2-methyl-4- t-butylphenyl analog (17) was virtually nontoxic to the honey bee, although it was still effective against the house fly. 

Toxicological Properties of IJ-Arylsulfenyl and 1 -Alkylsulfenyl Derivatives of Insecticidal Methylcarbamates... 

The results of a comparative metabolism study of an aryl-sulfenyl derivative of carbofuran [2,2-dimethy1-2,3-dihydro-benzofuranyl-7 -methyl-N-(2-toluenesulfenyl)carbamate] in the house fly and white mouse Indicated the selective action of this compound to be a consequence of different metabolic pathways in insects and mammals (12). The arylsulfenyl group on the carbamate moiety allows the mammal to carry out metabolic reactions leading to less toxic products which are rapidly conjugated, while the toxic parent methylcarbamate is formed in the insect. 

A number of reports describing a wide variety of N-arylsulfenyl and N-alkylsulfenyl derivatives of different types of methylcarbamate insecticides have been disclosed in the patent literature (15,16,17,18,19). Two of these reports (18,19) describe trichloromethyl- or trlfluoromethylsulfenyl derivatives of the highly toxic methylcarbamates carbofuran and aldlcarb. 

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