Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-10-14
2000-06-20
McKane, Joseph
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D24912
Patent
active
060779594
ABSTRACT:
A process for preparing an alkyl .alpha.-2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4 -triazol-1-yl]-2,4-substituted-benzene-propanoate herbicide, by reacting an alkyl .alpha.-acetyl-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-t riazol-1-yl]-2,4-disubstituted-benzene-propanoate, Intermediate D, first with sodium hypochlorite, then with a base, and recovering the herbicide. Intermediate D is prepared by reacting a 1-(2, 4-disubstituted-5-halophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo- 1H-1,2,4-triazole, Intermediate B, with an alkyl alkanoate in the presence of a palladium catalyst and a tertiary amine. Intermediate B is prepared by reacting a 1-(2,4-disubstituted-phenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1,2,4-triazole with a halogenating agent in the presence of an acid. The 2,4-substituents are independently selected from halo, alkyl, cycloalkyl, alkoxy, nitro, or hetercyclyl.
REFERENCES:
patent: 5125958 (1992-06-01), Poss
patent: 5621112 (1997-04-01), Ager et al.
Theodoridis G: "Structure-Activity Relationships Of Herbicidal Aryltriazolinones", Pesticide Science, vol. 50, No. 4, Aug. 1997, pp. 283-290.
Crispino Gerard A.
Goudar Jaidev S.
FMC Corporation
McKane Joseph
Sackey Ebenezer
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