Patent GB-802096-A (GB)
Title: New benztriazole derivatives and fungicidal compositions containing them
IPC: C07D249/18
Filed: 1956-06-14
Abstract: The invention comprises benztriazole derivatives of the formula <FORM:0802096/IV (b)/1> wherein X1 represents a halogen atom or a nitro group and X2 represents hydrogen, a halogen atom or a nitro group. The novel compounds may be prepared by reacting trichloromethane sulphenyl chloride in the presence of an acid binding agent with a benztriazole of the formula <FORM:0802096/IV (b)/2> where X1 and X2 are as above-defined.  The reaction may be performed in a two-phase system by dissolving the substituted benztriazole in diluted caustic soda lye, adding chloroform or another organic solvent which is insoluble in water and adding trichloromethane sulphenyl chloride while stirring vigorously. Examples of substituted benztriazoles are the 5-chloro-, the 5-bromo-, the 4-nitro-, the 5-nitro-, the 4,6-dinitro-, and 4-nitro-5-chloro-derivatives.  The new benztriazole derivatives are useful as the active ingredients in fungicidal compositions.  In examples: (1) 5-chlorobenztriazole is dissolved in caustic soda lye, chloroform is added, and the trichloromethane sulphenyl chloride is added dropwise with stirring at 20 DEG  C. and after some hours the two isomers 1-trichloromethane-sulphenyl-5-chlorobenztriazole and 1 - trichloromethane sulphenyl - 6 - chlorobenztriazole are recovered from the organic phase; (2) trichloromethane sulphenyl chloride is added dropwise to a mixture of 4-nitrobenztriazole, caustic soda lye and chloroform and 1-trichloromethane sulphenyl-4-nitrobenztriazole is recovered.  1 - Trichloromethane sulphenyl-4-nitro-5-chlorobenztriazole is obtained in an analogous manner.ALSO:Fungicidal compositions comprise a benztriazole derivative of the formula:  <FORM:0802096/VI/1> wherein X1 represents halogen atom or a nitro group, and X2 represents hydrogen, a halogen atom or a nitro group, as active ingredient, together with a carrier. (For preparation of the benztriazole derivatives see Group IV (b)). The new benztriazole derivatives may be used in finely distributable form combined with solid pulverulent carriers such as talc, kaolin, bole, bentonite, chalk or ground limestone.  The active ingredients may be suspended in water by addition of wetting and dispersing agents or capillary-active substances, or after being dissolved in organic solvents, they can be emulsified in water by adding suitable emulsifiers.  The active ingredients may also be dissolved in organic solvents, e.g. chlorinated hydrocarbons such as trichlorethylene, or in medium petroleum fractions, possibly with addition of auxiliary solvents such as acetone or higher ketones.  In examples: (3) 2-5 parts of 1-trichloromethane sulphenyl-4-nitrobenztriazole or 1-trichloromethane sulphenyl-4,6-dinitrobenztriazole is finely ground with 98-95 parts talc; (4) 10 parts of 1 - trichloromethane sulphenyl - 5 - nitrobenztriazole is ground with 82 parts of kaolin or chalk and mixed with 8 parts of an ethylene oxide-alkyl phenol condensation product to produce a concentrate which may be mixed with water to produce a spraying agent; (5) 20 parts of the isomeric mixture of 1-trichloromethane sulphenyl-5-chlorobenztriazole and 1-trichloromethane sulphenyl-6-chlorobenztriazole, 50 parts of xylene and 30 parts of ethylene oxide-alkyl phenols condensation products are mixed together to obtain an emulsion concentrate.