The Upjohn Co.

Pharmacia & Upjohn Company

Stephen J Nelson

Fred E Dutton

Byung H Lee

Clifford E Sacks

Marcfortine/paraherquamide derivatives useful as antiparasitic agents

This invention pertains to a new method for killing and controlling worms (Helminths), new formulations for killing and controlling worms in animals, new chemical compounds, and a new synthesis of northern hemisphere intermediates for the synthesis of milbemycin and avermectin macrolides.

Novel [5.5]-spiroketals

Anthelmintic spiroketals and method of use

Process for preparing aldol intermediates

Anthelmintic spiroketals useful for killing parasitic worms

Spiroketals and process for preparing same

This invention pertains to some new organic compounds, to a process for preparing them, and to formulations of them suitable for pesticidal use. The invention is more particularly directed to imidic acid derivatives of N-thio(methyl)carbamates.

N-imidoylthio(methyl)carbamates

New phosphinic acid derivatives of aminothio methylcarbamates. The new compounds are active against insects, mites and nematodes.

N-[(phosphinyl) amino]thio- and

N-Imidoylthio(methyl)carbamates and methods for controlling insects

Phenylcarbamoylbenzimidates of the formula ##STR1## 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. These compounds are useful for controlling susceptible insect and arachnoid pests.

Imino ethers useful for controlling insect and arachnoid pests

This invention pertains to novel processes for preparing phosphorus derivatives of aminothiomethylcarbamates using as intermediates corresponding phosphorus derivatives of aminothiocarbamic halides. The carbamates are useful as pesticides against insects, mites, and nematodes. Two processes for preparing the corresponding intermediates are described. One preparation generally reacts an appropriate N-chlorothiophosphoramide with N-methylcarbamoyl halide. The other preparation generally reacts an N-chlorothiomethylcarbamoyl halide with an appropriate phosphoramide. The intermediate will react with various alcohols to produce the desired carbamates in the process of the invention.

Process for making phosphorus derivatives of aminothiomethylcarbamates

Processes for making phosphorus derivatives of aminothiomethylcarbamates

Phenylcarbamoylbenzimidates of the formula ##STR1## wherein X.sub.1 is selected from the group consisting of methyl, trifluoromethyl, chlorine, fluorine and bromine; X.sub.2 is selected from the group consisting of hydrogen, methyl, trifluoromethyl, chlorine, fluorine and bromine; R is alkyl of from 1 to 5 carbon atoms; X.sub.3 and X.sub.4 can be the same or different and are selected from the group consisting of hydrogen, chlorine and bromine; X.sub.5 is selected from the group consisting of hydrogen, chlorine, bromine and trifluoromethyl; and X.sub.6 is selected from the group consisting of cyano and nitro; with the proviso that when X.sub.1 and X.sub.2 are chlorine or when X.sub.1 is fluorine and X.sub.2 is hydrogen then R, X.sub.3, X.sub.4, X.sub.5 and X.sub.6 are respectively not 1-methylethyl, chlorine, hydrogen, chlorine and nitro; with the further proviso that when X.sub.1 is fluorine and X.sub.2 is hydrogen then R, X.sub.3, X.sub.4, X.sub.5 and X.sub.6 are respectively not 1-methylethyl, chlorine, hydrogen, hydrogen and nitro; and with the further proviso that when X.sub. 1 is florine or methyl and X.sub.2 is hydrogen then R, X.sub.3, X.sub.4, X.sub.5 and X.sub.6 are respectively not ethyl, hydrogen, hydrogen, hydrogen and nitro; and with the proviso that when X.sub.1 and X.sub.2 are florine, then R, X.sub.3, X.sub.4, X.sub.5 and X.sub.6 are respectively not ethyl, chlorine, hydrogen, chlorine and nitro.

Pesticidal phenylcarbamoylbenzimidates

This invention pertains to novel phosphorus derivatives of aminothiocarbamic halides and processes for their preparation. The carbamic halides are readily prepared by two general procedures. In one procedure an appropriate N-(chlorothio)phosphorus amide reactant is readily prepared by reacting the corresponding phosphorus amide with sulfur dichloride which reactant will react with N-methylcarbamoyl halide so as to produce the corresponding object compounds of this invention. In a different procedure the same compounds that are the object of this invention are prepared by reacting an appropriate corresponding phosphorus amide with an N-chlorothiomethylcarbamoyl halide reactant which reactant is readily prepared by reacting N-methylcarbamoyl halide with sulfur chloride. The novel compounds of this invention are intermediates for the preparation of pesticides.

Growing community of inventors

Comstock Township, MI, United States of America

Stephen J Nelson