Compounds 1 - carbamoyl - N - carbamoiloxiformimidatos useful as pesticides, compositions containing Same, Methods for their Preparation and Intermediates useful in said process compounds

摘要

1344716 1 - Carbamoyl - N - hydroxy - and 1 - carbamoyl - N - carbamoyloxyformimidates E I DU PONT DE NEMOURS & CO 6 July 1971 [15 July 1970] 31587/71 Heading C2C [Also in Division A5] The invention comprises compounds of the formula wherein R 1 is glycidyl; alkyl of 1 to 4 carbon atoms; alkenyl of 3 or 4 carbon atoms; alkynyl of 3 or 4 carbon atoms; cycloalkyl of 3 to 6 carbon atoms; or alkyl of 1 to 4 carbon atoms substituted by 1 to 3 halogen atoms or by a methoxy, ethoxy, nitro, cyano, hydroxy, methylthio, carboxy, carbomethoxy, carboethoxy, amino, methylamino, ethylamino, dimethylamino, methylethylamino, methylpropylamino or diethylamino group; each of R 2 and R 3 which may be the same or different, is hydrogen; alkyl of 1 to 4 carbon atoms; alkenyl of 3 or 4 carbon atoms; methoxy; or cycloalkyl of 3 to 5 carbon atoms; with the proviso that R 2 and R 3 do not contain a total of more than 7 carbon atoms, and are not both cycloalkyl or both methoxy; or R 2 and R 3 together are alkylene of 2 to 6 carbon atoms; and Q is hydrogen; or a group of the formula wherein R 4 is hydrogen; alkyl of 1 to 3 carbon atoms; allyl; or propargyl; and R 5 is hydrogen; or methyl; the production of compounds as above in which Q is H by reacting in an inert organic solvent at - 70‹ C. to + 25‹ C. with two equivalents of base, the second (and preferably also the first) being an alcoholate R 1 OM in which M is Na, Li, K or Cs; and the production of other compounds by reacting the compounds in which Q is H with (i) sodium cyanate and hydrochloric acid at 0-10‹ C. to give compounds in which Q is NH 2 CO-; (ii) R 4 NCO in an inert solvent to give compounds in which Q is R 4 NHCO-; and (iii) NaH in an inert solvent followed by a substituted carbamoyl chloride to give compounds in which Q is R 4 R 5 NCO- (neither R 4 nor R 5 being hydrogen). Compounds as defined above in which Q is R 4 R 5 NCO- are pesticides (see Division A5).