title: Synthesis and herbicidal activity of 2-cyano-3-substituted-pyridinemethylaminoacrylates.
abstract: Two series of 2-cyano-3-substituted-pyridinemethylaminoacrylates, namely 12 new (Z)-2-cyano-3-methylthio-3-substituted-pyridinemethaneaminoacrylates and 10 new (Z)-2-cyano-3-alkyl-3-substituted-pyridinemethaneaminoacrylates, were synthesized as herbicidal inhibitors of photosystem II (PSII) electron transport. All of these compounds were confirmed by (1)H NMR, elemental, IR, and mass spectrum analyses. Their herbicidal activities were evaluated. Some compounds exhibited excellent herbicidal activities, even at a dose of 75 g/ha. A suitable substituent at the 2-position of the pyridine ring and the well-fit group at the 3-position of acrylate were essential for high herbicidal activity. 2-Cyanoacrylates containing a substituted pyridine ring provide higher herbicidal activities than parent compounds containing phenyl. These PSII inhibitor herbicides are safe to corn, which is a major crop in China.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
authors.forename: Qingmin
authors.initials: Q
authors.lastname: Wang
authors.forename: Huikai
authors.initials: H
authors.lastname: Sun
authors.forename: Huanyan
authors.initials: H
authors.lastname: Cao
authors.forename: Muru
authors.initials: M
authors.lastname: Cheng
authors.forename: Runqiu
authors.initials: R
authors.lastname: Huang
mesh_terms: D003487:Cyanoacrylates / Q000138:chemical synthesis* / Q000494:pharmacology*; D006540:Herbicides / Q000494:pharmacology*; D015394:Molecular Structure; D045322:Photosynthetic Reaction Center Complex Proteins / Q000037:antagonists & inhibitors; D045332:Photosystem II Protein Complex; D011725:Pyridines / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D003487:Cyanoacrylates; D006540:Herbicides; D045322:Photosynthetic Reaction Center Complex Proteins; D045332:Photosystem II Protein Complex; D011725:Pyridines