Patent GB-1088417-A (GB)
Title: Phosphorus substituted diamides and pesticidal compositions containing them
Inventor: BARNAS EUGENE FRANCIS
IPC: C07F9/30
Filed: 1964-11-02
Abstract: The invention comprises compounds of the formula <FORM:1088417/C2/1> where A, D, R and R1 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl, haloalkyl, nitroalkyl, cyanoalkyl, or acyl groups containing from two to ten carbon atoms, and provided that a maximum of one of A and D is an acyl group, and that a maximum of one of R and R1 is an acyl group, m and n are 0 or 1, E and Q are independently alkylene groups containing from one to ten carbon atoms, T is hydrogen or an alkyl group containing from one to four carbon atoms, Z and Z1 are independently oxygen or sulphur and R11 and R111 are independently alkyl, alkoxy, alkythio, aryl, aryloxy, arylthio, aralkyl, aralkoxy or aralkylthio groups containing from one to ten carbon atoms.  They may be prepared by reacting a compound having the formula <FORM:1088417/C2/2> where Q, T, m and n are as defined above and G is chlorine or bromine, J is hydrogen or an alkyl group, M is an alkylene group such that <FORM:1088417/C2/3> equals E in Formula I, a is zero or one, X is halogen and Y is halogen or an alkoxy group with at least one amine having the formula HN(OR)R1 or HN(OA)D and the resulting diamide is thereafter reacted with a phosphorus acid having the formula HZ1P(Z)(R11)(R111) or an alkali metal salt of such acid. Where the two amide groups are to be identical in the final product the diacid halide is reacted with sufficient amine of the formula HN(OR)R1 to react with both acid halide groups.  If the two amide groups are to be non-identical a mono-ester-mono acid halide is reacted with an amine of the formula HN(OR)(R1) to replace the acid halide group, the ester group is hydrolysed to the acid which is converted to the acid chloride and reacted with an amine HN(OA)D or the ester can be reacted directly with the amine.  The suitable acid halides can be prepared from the appropriate haloalkyl or alkenyl diacids or their anhydrides by converting to the diacid halide or by reaction with an alcohol and then converting the half acid to the monoester-mono acid halide.  In the examples fumaryl chloride is reacted with (i) N-methoxy N-methylamine hydrochloride, (ii) N-isopropoxy-N-methylamine hydrochloride and (iii) N-methoxy - N - n - propylamine hydrochloride to give the corresponding fumaramides which are then reacted with 0,0-dimethyldithiophosphate to give the corresponding phosphorus substituted succinamides.  The compounds are useful as pesticides, particularly as insecticides and miticides (see Division A5).ALSO:A pesticidal composition comprises an inert carrier and a compound of the formula:  <FORM:1088417/A5-A6/1> where A, D, R and R1 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl, haloalkyl, nitroalkyl, cyanoalkyl or acyl groups containing from 2 to ten carbon atoms, and provided that a maximum of one of A and D is an acyl group, and that a maximum of one of R and R\sv is an acyl group, m and n are 0 or 1, E and Q are independently alkylene groups containing from one to ten carbon atoms, T is hydrogen or an alkyl group containing from one to four carbon atoms, Z\sv and Z are independently oxygen or sulpur and R\yF and R\yG are independently alkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, aralkyl, aralkoxy or aralkylthio groups containing from one to ten carbon atoms (see Division C2).  The compositions may be solids such as dusts, granules or wettable powders or liquids such as solutions or emulsifiable concentrates.  Dusts can be prepared by grinding and blending the active compound with a solid inert carrier such as the talcs, clays, silicas and pyrophyllite. Granular formulations can be prepared by impregnating the compound, usually dissolved in a solvent, on to and into granulated carriers such as the attapulgites or the vermiculites. Wettable powders can be prepared by incorporating wetting agents into concentrated dust compositions.  The active compounds may also be used as solutions in solvents such as kerosene or xylene and in this form may be used as aerosols.  Preferred liquid compositions are emulsifiable concentrates which comprise an active compound and as the carrier a solvent and an emulsifier such as non-ionic or mixtures of non-ionic with anionic surface active agents.  An example describes a composition of active compounds dissolved in acetone which is then dispersed in distilled water containing an alkyl aryl polyether alcohol type emulsifier.