NOVEL THIADIAZOLES

摘要

1434699 Pesticidal phosphorus-containing thiadiazole derivatives ROUSSEL-UCLAF 24 Oct 1974 [26 Oct 1973] 46856/74 Headings C2P and C2C Novel compounds of Formula I where R is C 1-3 alkyl, X is O or S, X is -O-, -S-, -NH- or -NC 1-3 alkyl-, n is 1 to 4 and R1 is H, CN, alkoxycarbonyl, C 1-3 alkoxy, C 2-4 alkenyl, phenyl or phenyl substituted by 1 or 2 halogen atoms, C 1-3 alkyl radicals and/or C 1-3 alkoxy radicals; may be prepared by reacting a compound of Formula II with a compound of Formula III where Hal is halogen. The starting materials of Formula II are prepared by ring closure of a compound of Formula IV where A is CN or alkoxycarbonyl and M is H or alkali metal, ring closure being carried out by oxidation where A is CN and by reaction with ammonia in the presence of an alkali metal hypohalite where A is alkoxycarbonyl. Intermediates of Formula IV are prepared as follows: (a) S - p - chlorobenzyl - S - potassium - N - cyanodiethioimidocarbonate by reacting dipotassium N-cyano-dithioimidocarbonate with p - chlorobenzyl chloride; (b) N,N - dimethyl - N1- ethoxycarbonyl-thiourea by reacting dimethylamine with ethoxycarbonyl isothiocyanate; (c) O - p - chlorobenzyl - S - potassium - N - cyanothioimidocarbonate by reacting sodium hydride with p-chlorobenzyl alcohol and carbon disulphide to give S-sodium-O-p-chlorobenzyl-dithiocarbonate, methylating this to give S-methyl-O- p-chlorobenzyl-dithiocarbonate and reacting this with cyanamide and potassium methylate; (d) O - n - butyl - S - sodium - N - cyano - dithiocarbonate as in (c) via S-potassium-O-n-butyldithiocarbonate and S - methyl - O - n - butyldithiocarbonate; (e) O - methyl - S - potassium- N-cyanothioimidocarbonate by reacting dimethylthiocarbonate with cyanamide and potassium methylate; and (f) O-n-propyl-S-sodium-N- cyano - thioimidocarbonate as in (c) via S- potassium - O - n - propyl - dithiocarbonate and S-methyl-O-n-propyl-dithiocarbonate. The compounds of Formula I have insecticidal and nematocidal properties and may be used as the active ingredients in conventional pesticidal compositions.