Patent GB-1229853-A (GB)
IPC: C07F9/12
Filed: 1968-06-13
Abstract: 1,229,853. Oxime phosphates; phosphonates; phosphinates and phosphoroamidates. STAUFFER CHEMICAL CO. 13 June, 1968 [16 June, 1967; 20 May, 1968], No. 28087/68. Heading C2C. [Also in Division A5] Novel oxime-containing phosphates, phosphonates, phosphinates and phosphoroamidates of the general formula in which X and Y are independently oxygen or sulphur, R is lower alkyl or lower alkoxy (up to 6 C atoms), R 1  is lower alkyl or lower alkoxy (up to 6 C atoms), amino, lower alkyl-substituted amino or phenyl, Q is hydrogen, divalent tetramethylenediene - 1,3, lower alkoxy or lower alkyl (up to 4 carbon atoms), nitro, halogen or combinations thereof, or lower dialkyl substituted thionophosphoryloxy, R 2  is hydrogen, lower alkyl (up to 4 C atoms) or phenyl, and R 3  is one of the following: (a) hydrogen, (b) substituted carbonate and thiocarbonate-forming groups of the type in which Z is oxygen or sulphur and R 4  is lower alkyl (1 to 4 carbon atoms) or #-chloro lower alkyl (2 to 4 C atoms), (c) carbamate-forming groups of the type in which R 5  and R 6  are independently hydrogen, alkyl having 1 to 10 C atoms, substituted alkyl having 1 to 6 C atoms (substituent is hydroxy, halogen, amino, dialkylamino, lower alkoxy or tetrahydrofuryl), lower alkenyl (2 to 4 C atoms) carboalkoxy alkyl having a total of from 3 to 8 C atoms, cycloalkyl having from 3 to 6 C atoms, 2-thiazolyl, phenyl, naphthyl, or substituted phenyl (substituent is halogen, lower alkyl, lower alkoxy, lower alkylthio, lower dialkyl-amino, having 1 to 4 C atoms, nitro, cyano, trifluoromethyl or combinations thereof) or in which is an N-containing heterocyclic radical selected from morpholino, piperazino, N-methyl piperazino, pyrrolidono, piperidino, hexamethyleneimino, pyrryl, indolyl, imidazolyl, benzimidazolyl, pyrazolyl, 1,3 - oxazolidino, and 1,3- thiazolidino, (d) groups of the type in which R 7  is alkyl having 1 to 8 C atoms, trichloromethyl, lower alkenyl having from 2 to 4 C atoms or the radical -(CH 2 )m-SR in which m is 1 or 2, R is alkyl having 1 to 6 C atoms, alkenyl having 2 to 4 C atoms, phenyl or substituted phenyl (substituent being halogen, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms), (e) lower alkyl sulphonyl having from 1 to 6 C atoms, (f) lower alkyl substituted thionophosphoryl or (g) 2,2,2 - trichloro - 1 - hydroxyethyl, 4 - cyanophenyl, 2,4,5 - trichlorophenyl, or 4 - methylthiophenyl, are prepared by reacting the appropriate substituted phosphoryl, phosphonyl or phosphinyl oxy or thio benzaldehyde (R 2  = H) or phenyl lower-alkyl ketone (R 2  = lower alkyl) with hydroxylamine hydrochloride to give the corresponding oxime, which is then further reacted (unless R 3  = H) with the appropriate substituted isocyanate, acid chlorides, chloroformate, chlorothiolformate, sulphonyl chloride, N - mono or N,N - disubstituted carbamyl chlorides, substituted thionophosphoryl chloride or anhydrous trichloroacetaldehyde. The compounds have pesticidal properties. 3 - O,O - diethylphosphorothioyloxy benzaldehyde is prepared by reacting O,O - diethylthionophosphoryl chloride with 3-hydroxybenzaldehyde in the presence of K 2 CO 3 .