Akihiko Mine

The mechanism of bentazon selectivity

Abstract Absorption, translocation and metabolism of [14C]3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide (bentazon) by several plant species were investigated to determine the mechanism of bentazon selectivity. Marked selective phytotoxicities were observed between resistant rice (Oryza sativa L.) and susceptible Cyperus serotinus Rottb. when treated with bentazon. Absorption and transolcation of bentazon did not differ greatly between highly resistant rice and susceptible C. serotinus. However, a marked difference in bentazon metabolism occurred between the two species. In rice about 80% of the absorbed bentazon was metabolized within 24 h, and after 7 days about 85% was converted to a major water-soluble metabolite and unchanged bentazon was only 5%. In C. serotinus 50–75% of the radioactivity was unchanged bentazon after 7 days. Large amounts of water-soluble metabolites were detected in root-treated resistant plants such as barnyardgrass (Echinochloa crus-galli Beauv.), soybean (Glycine max Merr.) and corn (Zea mays L.), but only small amounts were present in such susceptible plants as Sagittaria pygmaea Miq. and Eleocharis kuroguwai Ohwi. Therefore, the mechanism of bentazon selectivity appears to be a difference between resistant and susceptible species in their ability to metabolize and detoxify bentazon. The major metabolite in rice was identified as 6-(3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide)-O-β-glucopyranoside, determined by GC-MS, NMR, IR and gas chromatography after hydrolysis with sulfuric acid or β-glucosidase.

Mode of action of bentazon: Effect on photosynthesis

Abstract Bentazon, 3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide is effective for weed control in flooded rice fields not only as a foliar treatment but also as a flooded-water or paddy soil treatment. Generally the herbicidal effect develops slowly only after translocation of the herbicide has occurred, but when the weeds contacted directly with relatively high concentrations of the herbicide, the effects appear rather rapid. The slow herbicidal effect appears to be an important mode of action of bentazon applied practically on weeds under flooded rice field conditions. The slow effect may be caused by inhibition of photosynthesis as supported by the following experimental results: a) Bentazon inhibited the Hill reaction in isolated chloroplasts; b) bentazon rapidly inhibited photosynthetic CO 2 fixation in susceptible Cyperus serotinus and other plants; c) the herbicidal effects appeared much slower when bentazon was applied as a flooded-water treatment; d) bentazon injury was prevented by endogenous or exogenously supplied carbohydrates.

Structure-activity study of herbicidal N-chloroacetyl-N-phenylglycine esters

Abstract N -Chloroacetyl- N -phenylglycine esters were shown to exert various degrees of growth inhibiting activity against young shoots of annual grasses. The activity against the rice plant and barnyard-grass was determined for 58 derivatives where either the aromatic substituent or ester moiety was modified. The structure-activity relationships were analyzed using physicochemical parameters of the molecule such as log P , σ, and E s , and regression analysis. By comparing the correlations derived for the rice plant and barnyard-grass, the selectivity in herbicidal activity is discussed.