SYNTHESIS AND SELECTIVE HERBICIDAL ACTIVITY OF METHYL (E,Z)-[[[1-[5-[2-CHLORO-4-(TRIFLUOROMETHYL)PHENOXY]-2-NITROPHENYL]-2-METHOXYETHYL-IDENE]AMINO]OXY]ACETATE AND ANALOGOUS COMPOUNDS

In an extensive investigation on the effects of a broad range of 3′-substituent groups in the series of compounds represented by 2-chloro-4- (trifluoromethyl)-3′- (substituted)-4′-nitrodiphenyl ethers, which is known to be generally characterized by potent herbicidal activities, those having 1- [(carbalkoxymethoxy)imino]-2-methoxyethyl substituents at the 3′-position, i.e., the ortho position to the nitro group of the benzene ring, were found to exhibit increased herbicidal activity against broadleaf weeds together with an apparent tendency for reduced crop injury. In the present study, 22 deriva tives of (E,Z)-[[[1-[5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene] am ino] oxy] ace tic acid were synthesized and evaluated for herbicidal activity against grass and broadleaf weeds. Among them, the title compound (Code No. AKH-7088) was found to exhibit particularly excellent potential for the selective control of a wide spectrum of broadleaf weeds in soybeans, with control of current problem weeds such as velvetleaf, cocklebur, and jimsonweed at postemergence application rates of 0.1-0.2 kg/ha and excellent soybean tolerance. © 1990, American Chemical Society. All rights reserved.