title: Syntheses and herbicidal activities of novel triazolinone derivatives.
abstract: Protoporphyrinogen oxidase (Protox, EC 1.3.3.4) has been identified as one of the most important action targets of herbicides. To search for novel Protox inhibitors, a series of title compounds 1, 2, and 3 were designed and synthesized by introducing three types of pharmacophores, cyclic imide, phenylurea, and ( E)-methyl 2-methoxyimino-2- o-tolylacetate, into the scaffold of triazolinone. The bioassay results indicated that the resulting cyclic imide-type triazolinones 1 displayed much better herbicidal activities than phenylurea-type triazolinones 2. Most fortunately, compound 3, methyl 2-[3-methyl-(2-fluoro-4-chloro-5-ethylsulfonamidephenyl)-4,5-dihydro-5-oxo-1 H-1,2,4-triazol-4-yl]methylenephenyl-2-( E)-methoxyiminoacetate, was found to be the most promising candidate due to its comparable herbicidal activity at 75-150 g of active ingredient/ha with the commercial product sulfentrazone. On the basis of test results of herbicidal spectrum and crop selectivity, compound 3 could be developed as a postemergent herbicide used for the control of broadleaf weeds in rice fields.
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
authors.forename: Yan-Ping
authors.initials: YP
authors.lastname: Luo
authors.forename: Li-Li
authors.initials: LL
authors.lastname: Jiang
authors.forename: Guo-Dong
authors.initials: GD
authors.lastname: Wang
authors.forename: Qiong
authors.initials: Q
authors.lastname: Chen
authors.forename: Guang-Fu
authors.initials: GF
authors.lastname: Yang
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D006540:Herbicides / Q000737:chemistry / Q000494:pharmacology*; D012275:Oryza / Q000254:growth & development; D050768:Protoporphyrinogen Oxidase / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis / Q000494:pharmacology; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D004791:Enzyme Inhibitors; D006540:Herbicides; D013449:Sulfonamides; D014230:Triazoles; C529387:methyl 2-(3-methyl-(2-fluoro-4-chloro-5-ethylsulfonamidephenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-4-yl)methylenephenyl-2-methoxyiminoacetate; D050768:Protoporphyrinogen Oxidase