N-(.alpha.-Aminoalkylidene)phosphor- and phosphonamidates, and method for controlling insects

#This invention relates to new compositions of matter and more specifically relates to new chemical compounds of the formula ##STR4## wherein X.sup.1 and X.sup.2 are independently selected from the group consisting of oxygen and sulfur; m is the integer 0 or 1; R.sup.1 is selected from the group consisting of hydrogen and alkyl; R.sup.2 is alkyl; R.sup.3 and R.sup.4 are independently selected from the group consisting of hydrogen and alkyl; R.sup.5 is selected from the group consisting of hydrogen, alkyl, alkoxy, alkylthio, amino and ##STR5## WHEREIN Y is selected from the group consisting of alkyl, halogen, alkoxy, alkylthio, nitro and cyano; and n is an integer from 0 to 3; and R.sup.6 is selected from the group consisting of alkyl, alkenyl, alkoxyalkyl and ##STR6## WHEREIN Z is selected from the group consisting of alkyl, halogen, alkoxy, alkylthio, nitro and cyano; and p is an integer from 0 to 3.

#The compounds of the present invention are useful as insecticides.

#In a preferred embodiment of the present invention X.sup.1 and X.sup.2 are independently selected from the group consisting of oxygen and sulfur; m is the integer 0 or 1; R.sup.1 is selected from the group consisting of hydrogen and lower alkyl; R.sup.2 is lower alkyl; R.sup.3 and R.sup.4 are independently selected from the group consisting of hydrogen and lower alkyl; R.sup.5 is selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, lower alkylthio, amino and ##STR7## wherein Y is selected from the group consisting of lower alkyl, halogen, lower alkoxy, lower alkylthio, nitro and cyano; and n is an integer from 0 to 3; and R.sup.6 is selected from the group consisting of lower alkyl, lower alkenyl, lower alkoxyalkyl and ##STR8## wherein Z is selected from the group consisting of lower alkyl, halogen, lower alkoxy, lower alkylthio, nitro and cyano; and p is an integer from 0 to 3.

#Ethylthionophosphonic dichloride (47.6 grams; 0.29 mole), methyl acetylacetate (33.6 grams; 0.29 mole) and benzene (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture was cooled to a temperature of about 10.degree. C. and triethylamine (29.3 grams; 0.29 mole) dissolved in benzene (20 ml) was added dropwise with vigorous stirring. After the addition was completed, the reaction mixture was allowed to warm to room temperature with continued stirring, resulting in the formation of a precipitate. The reaction mixture was then stirred for an additional period of about three hours at a temperature of from room temperature to about 45.degree. C. After this time the reaction mixture was filtered to remove the triethylamine hydrochloride precipitate. The precipitate was washed with benzene, and the washings were combined with the filtrate. The combined solution was then stripped of solvent under reduced pressure to yield the desired product 0-(1-methyl-2-methoxycarbonylvinyl) ethylthionophosphonic chloride as a pale yellow liquid.

#0-(1-Methyl-2-methoxycarbonylvinyl) ethylthionophosphonic chloride (4.84 grams; 0.02 mole), acetamidine hydrochloride (2.84 grams; 0.03 mole) and methylene chloride (50 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture was cooled to a temperature of about 10.degree. C., and a solution of sodium hydroxide (2.0 grams; 0.05 mole) in water (20 ml) was added dropwise with stirring. After the addition was completed, the reaction mixture was allowed to warm up to room temperature, and stirring was continued for a period of about 2 hours. After this time the organic phase was separated from the aqueous phase and was washed with water. The washed solution was then dried over anhydrous magnesium sulfate and was filtered. The filtrate was stripped of solvent under reduced pressure, leaving an oil. This oil was allowed to stand under vacuum for a period of about 1 hour to yield the desired product 0-(1-methyl-2-methoxycarbonylvinyl) N-(.alpha.aminoethylidene)ethylthionophosphonamidate.

#Isopropyl acetylacetate (41.7 grams; 0.29 mole) and benzene (100 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture was cooled to a temperature of about 10.degree. C., and ethylthionophosphonic dichloride (47.6 grams; 0.25 mole) was added thereto. The mixture was then stirred vigorously, and a solution of triethylamine (29.3 gram; 0.29 mole) in benzene (25 ml) was added dropwise over a period of about 60 minutes. After the addition was completed, stirring was continued while maintaining the temperature of the reaction mixture at about 10.degree. C. for a period of about 30 minutes. After this time the temperature of the mixture was allowed to rise to about 15.degree. C for a period of about 60 minutes. The mixture was thereafter warmed to room temperature and stirred for an additional 60 minutes and to about 45.degree. C. for about 2 hours. After this time the reaction mixture was filtered to remove triethylamine salt which formed as a precipitate. The filtrate was then dissolved in ether, resulting in additional precipitation of triethylamine salt. The mixture was again filtered and the filtrate stripped of solvents in a rotary evaporator under reduced pressure. The residue was subjected to distillation in a one foot Vigreaux column to yield the desired product 0-(1-methyl-2-isopropoxycarbonylvinyl) ethylthionophosphonic chloride.