Patent GB-998684-A (GB)
Title: Novel carbamic and thiocarbamic acid derivatives also containing a cyano group, and their use as pesticides
IPC: C07C333/02
Filed: 1962-08-16
Abstract: Agricultural compositions for combatting parasitic nematodes comprise an inert carrier and/or a fertilizer, with as active ingredient one or more compounds of the general formula <FORM:0998684/C1/1> where X1, X2, X3 independently represent O or S, R1 is H, methyl or ethyl, R2 is methyl or ethyl, A is preferably a straight-chain or branched-chain C2 to C4 alkylene chain wherein at least 2 C atoms separate X1 and X2.  Specific compounds exemplified have formulae NC-(CH2)2-S-(CH2)2-S-CS-NHCH3 NC-(CH2)2-O-(CH2)2-S-CS-NHCH3 <FORM:0998684/C1/2> NC-(CH2)2-O-(CH2)3-S-CS-NHCH3 NC-(CH2)2-O-(CH2)4-S-CS-NHCH3 <FORM:0998684/C1/3> <FORM:0998684/C1/4> <FORM:0998684/C1/5> <FORM:0998684/C1/6> Pulverulent diluents include talcum, diatomite, kaolin, bentonite, calcium carbonate, boric acid, tricalcium phosphate, synthetic fertilizers, e.g. solubilized calcium phosphate, potassium or ammonium salts, loess, phosphates or nitrates. The active ingredients may be incorporated emulsifiable petroleum based compositions which include non-ionic, cationic, anionic or pluronic emulsifiers or may be in solution with other halogenated nematocides, e.g. 1,2-di-bromo-3-chloropropene, dichlorbutene or mixtures thereof.  Nematodes stated to be capable of being affected are Meloidogyne arenaria, Pratylenchus, Ditylenchus dipsaci.  In the examples improvement in yields of tomatoes, bushy beans, and melons are recorded.ALSO:The invention comprises compounds of the general formula <FORM:0998684/C2/1> where X1, X2, X3 independently represent oxygen or sulphur, R1 is H1, methyl or ethyl, R2 is methyl or ethyl, A is preferably a straight chain or a branched chain C2 to C4 alkylene group, at least two C atoms of which bridge X1 and X2 and in particular the compounds represented by the formulae NC-CH2-CH2-S-CH2-CH2-S-CS-NHCH3 NC-CH2-CH2-O-CH2-CH2-S-CS-NHCH3 NC-CH2-CH2-O-CH2-CH2-S-CO -N(CH3)2 NC-CH2-CH2-O-CH2-CH2-CH2-S-CS -NHCH3 NC-CH2-CH2-O-(CH2)4-S-CS-NHCH3 <FORM:0998684/C2/2> NC-CH2-CH2-S-CH2-CH2-O-CO -N(CH3)2 NC-CH2-CH2-O-(CH2)3-S-CS -N(CH3)2 NC-CH2-CH2-S-CH2-CH2-O-CO -NHC2H5 and their preparation by the reaction of a compound of formula <FORM:0998684/C2/3> and a compound of formula NC-CH2-CH2-X1-A-Y, wherein one of Y and Z represents a halogen atom which is eliminated as an anion in the reaction and the other represents the group X2Q, where Q is hydrogen, an alkali or alkaline earth metal atom or ammonium group which is eliminated as a cation, or by the reaction in the presence of a base and/or solvent of acrylonitrile with a compound <FORM:0998684/C2/4>ALSO:Agricultural compositions for combatting parasitic nematodes comprise an inert carrier and/or a fertilizer, with as active ingredient one or more compounds of the general formula <FORM:0998684/A5-A6/1> where X1, X2, X3 independently represent O or S, R1 is H, methyl or ethyl, R2 is methyl or ethyl, A is preferably a straight chain or branched chain C2 to C4 alkylene chain, wherein at least 2 C atoms separate X1 and X2.  Specific compounds exemplified have formul <FORM:0998684/A5-A6/2> Pulverulent diluents include talcum, diatomite, kaolin, bentonite, calcium carbonate, boric acid, tricalcium phosphate, synthetic fertilizers, e.g. solubilized calcium phosphate, potassium or ammonium salts, loess, phosphates or nitrates.  The active ingredients may be incorporated emulsifiable petroleum based compositions which include non-ionic, cationic anionic or phenonic emulsifiers or may be in solution with other halogenated nematocides, e.g. 1,2-dibromo - 3 - chloropropene, dichlorobutene or mixtures thereof.  Nematodes stated to be capable of being affected are Meloidogyne aunaria, Pratyleuchus, Dityleuchus dipsachi.  In the examples, improvements in yields of tomatoes, bushy beans, and melons are recorded.