Abstract: A process for the production of an aryl triazolinones of the formula ##STR1## wherein R is lower alkyl and:X.sub.n is 2,4-dichloro-5-methylsulfonylamino; 2-chloro-5-methylsulfonylamino; 4-chloro-5-methylsulfonylamino; 3-methylsulfonylamino; 4-chloro; 2-chloro; 3-nitro; 4-chloro-3-nitro; 2-chloro-5-nitro; 2,4-dichloro-5-nitro; 2-fluoro; 2-4-chloro; 2,4-dichloro; 4-alkoxy; or 4-alkoxy-2-fluoro;which comprises treating, in a tert-butanol medium, an aryl hydrazine of the formula ##STR2## sequentially with (i) a C.sub.1 -C.sub.3 aldehyde, (ii) a cyanate and weak organic acid, and (iii) a hypohalous acid, a salt thereof, or a halogen.

Abstract: An improved process for the difluoromethylation of a 1-phenyl-1H-1,2,4-triazol-5-one at the 4-position of the triazole ring with chlorodifluoromethane significantly reduces the amount of base required for the process, thereby reducing the environmental impact of the process by reducing the amount of by-product salts in the waste stream. The improvement comprises reacting the triazolinone with potassium carbonate in a solvent such as dimethylformamide, at a carbonate to triazolinone ratio in the range of about 0.55 to 1.0; reducing the water content of the reaction mixture to below about 2400 ppm by distillation; heating the reaction mixture in a sealed autoclave to 110.degree. to 180.degree. C., adding a 10 to 15 percent molar excess of chlorodifluoromethane, heating the reaction mixture at a temperature of 140.degree. to 210.degree. C. for 5 to 60 minutes, and recovering the difluoromethylated triazolinone.

Abstract: A process for the production of aryl triazolinones of the formula ##STR1## wherein R is lower alkyl;X is independently halogen, lower alkyl, nitro, hydroxy, NHSO.sub.2 R', --N(SO.sub.2 R').sub.2, --N(R'(SO.sub.2 R' where R' is lower alkyl, and n is an integer from 0 to 3;which comprises treating, in a tert-butanol medium, an aryl hydrazine of the formula ##STR2## sequentially with (i) a C.sub.1 -C.sub.3 aldehyde, (ii) a cyanate and weak organic acid, and (iii) a hypochlorite, a salt thereof, or a halogen.