Patent GB-1057995-A (GB)
Title: New diazole compounds
IPC: C07D285/13
Filed: 1965-07-28
Abstract: The invention comprises diazole compounds of the formula <FORM:1057995/C2/1> in which R1 and R2, which may be the same or different, denote hydrogen atoms or alkyl groups, X1 and X2, which may be the same or different, each denotes an oxygen or sulphur atom, and R3 denotes a hydrogen atom or an alkyl group, a phenyl group which may carry a halogen, alkyl, alkoxy or hydroxy substituent, an aralkyl group of 7-12 carbon atoms, a cycloalkyl group of 3-6 carbon atoms, a 5- or 6-membered heterocyclic group containing one or more hetero oxygen, sulphur or nitrogen atoms, or a cyano, alkoxy, alkylthio, alkoxycarbonyl, alkylcarbamoyl or alkanesulphonyl group. The alkyl, alkoxy and alkane groups contain at most 4 carbon atoms. The compounds may be prepared by reacting a carbamoyl halide of the formula Hal-CO-N(R1)R2, in which Hal denotes a halogen atom, with a diazole of the formula <FORM:1057995/C2/2> or an alkali-metal derivative thereof.  Alternatively, the compounds in which R1 denotes a hydrogen atom may be prepared by reacting an isocyanate of the formula R2NCO with a compound of the second formula above.  Suitable reaction conditions are described in each case. The examples describe the manufacture of (1) 3 - methylcarbamoyl - 5 - propyl - 1,3,4 - oxadiazol - 2 - one, (2) 3 - methylcarbamoyl - 5 - t. - butyl - 1,3,4 - oxadiazol - 2 - thione, (3) 3 - dimethylcarbamoyl - 5 - t. - butyl - 1,3,4 - oxadiazol - 2 - thione, (4) 3 - methylethylcarbamoyl - 5 - t. - butyl - 1,3,4 - oxadiazol - 2 - one, and (5) 3 - methylcarbamoyl - 5 - ethyl - 1,3,4 - oxadiazol-2-one. Other obtainable products are listed.  The products are useful as insecticides (see Division A5). 5 - t. - Butyl - 1,3,4 - oxadiazol - 2 - thione, used in Example 2, is prepared by the action of thiophosgene on trimethylacetylhydrazine or by the cyclization of potassium trimethylacetyldithiocarbazinate in ethanol under reflux.  5-t.-Butyl-1,3,4-oxadiazol-2-one, used as potassium salt in Example 4, is prepared by the action of potassium ethoxide on 5-t.-butyl-1,3,4 - oxadiazol - 2 - one, which is itself prepared by the cyclization of trimethylacetylurea with potassium hypobromite in an alkaline medium.  5 - Ethyl - 1,3,4 - oxadiazol - 2 - one, used in Example 5, is prepared by the cyclization of propionylhydrazine with phosgene.ALSO:As insecticides, use is made of diazole compounds of the formula:- <FORM:1057995/A5-A6/1> in which R1 and R2, which may be the same or different, denote hydrogen atoms or alkyl groups, X1 and X2, which may be the same or different, each denotes an oxygen or sulphur atom, and R3 denotes a hydrogen atom or an alkyl group, a phenyl group which may carry a halogen, alkyl, alkoxy or hydroxy substituent, an aralkyl group of 7-12 carbon atoms, a cycloalkyl group of 3-6 carbon atoms a 5- or 6- membered heterocyclic group containing one or more hetero oxygen, sulphur or nitrogen atoms, or a cyano, alkoxy, alkylthio, alkoxycarbonyl, alkylcarbamoyl or alkanesulphonyl group.  The alkyl, alkoxy and alkanesulphonyl groups contain at most 4 carbon atoms (see Division C2).  The diazoles may be formulated as solid or liquid compositions by additon of solid or liquid diluents, a number of both of which are specified.  The liquid compositions may be solutions, suspensions emulsions or self-emulsifying concentrates, and they may contain dispersing agents, a number of which are also specified.  Examples are given.