6146. Metolachlor

Nomenclature

CAS number: 51218-45-2
2-Chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide; 2-chloro-6′-ethyl-N-(2-methoxy-1-methylethyl)acet-o-toluidide; α-chloro-2′-ethyl-6′-methyl-N-(1-methyl-2-methoxyethyl)acetanilide; metelilachlor; CGA-24705; Dual (Syngenta).
C15H22ClNO2; mol wt 283.79.
C 63.48%, H 7.81%, Cl 12.49%, N 4.94%, O 11.28%.

Description and references

Selective pre-emergence herbicide. Prepn: C. Vogel, R. Aebi, DE 2328340; eidem, US 3937730 (1973, 1976 both to Ciba-Geigy). Synthesis of stereoisomers: B. T. Cho, Y. S. Chun, Tetrahedron: Asymmetry 3, 337 (1992). Metabolism: L. L. McGahen, J. M. Tiedje, J. Agric. Food Chem. 26, 414 (1978). ELISA determn: T. S. Lawruk et al., J. Agric. Food Chem. 41, 1426 (1993). Review: G. Chesters et al., Rev. Environ. Contam. Toxicol. 110, 1-74 (1989); of biological activity and field trials: H. R. Gerber et al., Proc. 12th Br. Weed Control Conf. 787-794 (1974).

Chemical structure

Properties

Colorless liquid. bp0.001 100°. nD20 1.5301. Vapor pressure at 20°: 1.3×105 mm Hg. Soly in water at 20°: 530 ppm. Sol in most organic solvents. Partition coefficient (octanol/water): 2,800. LD50 in rats (mg/kg): 2780 orally; >3170 dermally (Gerber).

Derivative

S-Form.

Nomenclature

CAS number: 87392-12-9
Dual Gold (Syngenta).

Use

Herbicide.