Syntheses and herbicidal activities of novel triazolinone derivatives.
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.
Luo
Yan-Ping
YP
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
Jiang
Li-Li
LL
Wang
Guo-Dong
GD
Chen
Qiong
Q
Yang
Guang-Fu
GF
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*
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