• The Korean Journal of Pesticide Science
• /
• v.3 no.3
• /
• pp.11-19
• /
• 1999

A some of synthesized 2-(4-(6-chloro-2-benzoxazolyloxy)phenoxy)-N-phenyl propionamide derivativesa substrates were found to selectivity significantly with both rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-galli) for those her- bicidal activities with post emergence in up land. The selectivity of substrates against rice plant better than that of Fenoxaprop-ethyl. The structure activity relationship (SAR) n the selectivity of N-phenyl substituents were analyzed by the Free-Wilson and Hansch method. The SAR approach against barnyard grass is shown that the optimal ($({\pi})_{opt.}=1.60$) hydrophobicity and electron donating effects ($0<{\sigma}$ & 0$(ES)_{opt.}=0.87$) so that the herbicidal activity against rice plant can be decreased. The significance of these results on the selectivity between barnyard grass and rice plant is discussed. And it is assumed that the 2-ethoxy-3-methoxy-4-dimethylamino group substituent ($pI_{50}$=6.60, 1g/ha) is selected as the most highest herbicidal activity against barngard grass in green house.

• The Korean Journal of Pesticide Science
• /
• v.4 no.2
• /
• pp.21-28
• /
• 2000

A new fourty six 2-(4-(6-chloro-2-benzoxazolyloxy)phenoxy)-N-phenylpro- pionamide derivatives were synthesized and the herbicidal activities against rice plant and barnyard grass with pre-emergence in down land were measured. The structure activity relationships (SAR) between the activities and physicochemical parameters of the substituted(X) N-phenyl group in substrates were analyzed and discussed by Free- Wilson and Hansch method from the basis on the former study (Sung. et. al., 1999). The conditions of selective herbicide activity both the barnyard grass and rice plant are shown that the optimal hydrophobicity, $({\pi})_{opt.}=1.34$ and electron donating with field effect (F<0) of meta and ortho, para-substituted mono or disubstituent on the N-phenyl ring were found to contribute significantly. The herbicidal activities against barnyard grass are roughly the same as the results in up land whereas damage to rice plant in down land more increase than that of up land. Degradation products in water are 2-(4-(6-chloro-2-benzoxazolyloxy)phenoxy)propionic acid ((A)) (obs. pKa=4.35 & obs. logP=4.77) and 6-chloro-2-benzoxazolone (B) (obs. pKa=8.40 & obs. logP=2.90). These results were supposing that the hydrolysis product of substrates, (A) is comparatively absorbed in rice plant but not in barnyard grass. And it is assumed from the SAR equations that the 2,6-dimethyl-4-methoxymethyl group substituent ($pI_{50}=5.41$, 3g/ha) is selected as the most highest herbicidal activity against barnyard grass in green house.