Substituted bicyclic triazole, its preparation, harbicide containing the same and production of harbicide

NEW MATERIAL: The compounds of formula I {X is H or F; Y is halogen; Z is O or S; R 1 is (substituted) 1-6C alkyl, (substituted) 2-6C alkenyl, (substituted) 3-6C alkynyl, 3-7C cycloalkyl, CR 2 R 3 A [R 2 , R 3 is H, F or methyl; A is CO 2 R 4 (R 4 is 1-6C alkyl or the like) or the like]; n is 1-3; m is 0-3}. EXAMPLE: 2-(4-chlor-5-etoxycarbonylmethylthio-2-fluorophenyl)-5,6,7,8- tetrahydro-1,2,4-triazole[4,3-a]pyridine-3-(2H)-on. USE: Harbicides. PROCESS: The compound of formula II are reacted with the compounds of formula III (R 8 is 1-4C alkyl) in an inactive solvent in the presence of phosphorous pentaoxide. COPYRIGHT: (C)1989,JPO