The Development of Two Herbicides, Alloxydim-sodium and Sethoxydim

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  • 除草剤アロキシジムおよびセトキシジムの開発
  • 除草剤アロキシジムおよびセトキシジムの開発(〔日本農薬〕学会賞受賞論文)
  • ジョソウザイ アロキシジム オヨビ セトキシジム ノ カイハツ ニホン ノウヤ

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Both of alloxydim-sodium [Sodium salt of methyl 3-(1-allyloxyaminobutylidene)-6, 6-dimethyl-2, 4-dioxocyclohexylcarboxylate] and sethoxydim (±)-2-(1-ethoxyiminobutyl)-5-[2-(ethylthio) propyl]-3-hydroxycyclohex-2-enone are postemergence herbicides that provide excellent control of a wide range of grass weeds. The studies on them were started from the discovery of a new compound among the benzoxamate (miticide) derivatives having a weak herbicidal activity on grass weed. As a result of the research on the derivatives of various heterocyclic compounds such as pyrans, dimedones and barbituric acids, the dimedone derivatives were found to show the highest activity in postemergence treatment, and an alkoxyamino alkylidene moiety was indispensable on dimedone ring. Thus we selected out a compound from the dimedone derivatives and commercialized it in formulation of alloxydimsodium. It showed excellent activity on annual grasses at 1kg/ha approximately. However, the dosage more than 4kg/ha was needed to control perennial grasses completely, especially johnsongrass (Sorghum halepense). Further investigation was carried out to find out more potent herbicide. Before long, we found that some compounds with additional substituent, sulfur-containing alkyl group at 5-position of 1, 3-dioxocyclohexane ring instead of the gemdimethyl of dimedone, gave excellent control of annual and perennial grasses. A lot of the cyclohexane derivatives with a sulfur-containing alkyl side chain were synthesized and screened. As the result, we picked out a compound (sethoxydim) providing always high activity in field trials. Sethoxydim effectively controlled annual grasses and johnsongrass at 0.2-0.4kg/ha and 0.5kg/ha respectively, and showed excellent selectivity in numerous dicotyledonous crops. Some simulated rainfall and partial droplet application studies revealed that sethoxydim appeared to be readily absorbed and translocated in the plants. Two gramineous species, Festuca rubra and F. myuros were resistant as high as broadleaf weeds, while F. arundinacea and F. pratensis were susceptible. This difference in susceptibility could not explain by absorption, translocation and metabolism. Microscopic studies revealed that sethoxydim attacked the meristematic regions and inhibited the cell divisions, resulting in the occurrence of herbicidal action.

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