Evaluation of novel sulfonylurea derivatives with a fused heterocyclic moiety as paddy herbicides that control sulfonylurea‐resistant weeds

Abstract

Herbicidal activity and acetolactate synthase (ALS) inhibition of sulfonylurea derivatives with a fused heterocyclic moiety bonded to a sulfonyl group were investigated. Some compounds that had an imidazo [1,2-b]pyridazine moiety substituted at the 2-position by chlorine or methyl controlled sulfonylurea-resistant (SU-R) weeds and showed inhibitory activity to ALS prepared from SU-R Schoenoplectus juncoides shoot.There was a correlation between in vitro and whole-plant herbicidal activity of the compounds mentioned above against SU-R Schoenoplectus juncoides. Among them 1-(2-chloro-6-propylimidazo[1,2-b]pyridazin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea, propyrisulfuron, was selected for further evaluation. Propyrisulfuron effectively controlled paddy weeds at doses of 70 and 140 g a.i. ha -1 with good rice selectivity in a field trial.

Characterization of acetolactate synthase from sulfonylurea herbicide‐resistant Schoenoplectus juncoides

“…The occurrence and spread of the herbicide‐resistant paddy weeds are prevented by a mixture of herbicides with different modes of action, such as bromobutide, pyraclonil and benzobicyclon, or by a newly introduced SU herbicide, propyrisulfuron (Ikeda et al . ).…”

Herbicide‐resistant weeds in the Philippines: Status and resistance mechanisms

“…Examples of the herbicides that were introduced after the 1990s for grass control include thenylchlor, cafenstrole, flufenacet, fluthiamide, fentrazamide, indanofan, dithiopyr, thiazopyr, pyributicarb, oxadiargyl, pentoxazone, clethodim, butroxydim, pyriminobac, pyribenzoxim, etobenzamid and cumyluron. New herbicides that were introduced for grass control in the 2000s include pyriftalid, clefoxydim, metamifop, oxaziclomefone, flucetosulfuron and propyrisulfuron (Takahashi et al 2000;Tomlin 2000;Kanzaki et al 2001;Morita 2003;Kobayashi et al 2004;Murano et al 2007;Kobayashi & Tsunekawa 2010;Ikeda et al 2011;Krämer et al 2012;Lainsbury 2013). New herbicides with new modes of action are inhibitors of the enzymes that are involved in pigment synthesis and include protoporphyrinogen oxidase, deoxy-D-xylulose-5-phosphate synthase, hydroxyphenylpyruvate dioxygenase, phytoene desaturase and the inhibitors of cellulose biosynthesis (Krämer et al 2012).…”

Application of the Intermediate Derivatization Approach in Agrochemical Discovery

“…Imazosulfuron, pyrazosulfuron-ethyl, and propyrisulfuron are all good herbicides used in rice field. − Imazosulfuron, developed by Takeda Chemical Industries Ltd. (now Sumitomo Chemical Company Ltd.) in 1994, and pyrazosulfuron-ethyl, introduced by Nissan Chemical Industries Ltd. in 1990, both provide pre- or postemergence control of annual and perennial broad-leaved weeds and sedges also in wet-sown and transplanted rice crops with no damage to rice in normal use. , Another herbicide used for rice with innovative structure is propyrisulfuron launched in Japan in 2011. Its structure is very similar to that of imazosulfuron, but propyrisulfuron has an advantage over imazosulfuron by providing excellent herbicidal activity against weeds that show resistance to other commercialized sulfonylurea herbicides …”