Synthesis and herbicidal activity of 2-cyano-3-substituted-pyridinemethylaminoacrylates.
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.
Wang
Qingmin
Q
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Sun
Huikai
H
Cao
Huanyan
H
Cheng
Muru
M
Huang
Runqiu
R
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
D003487:Cyanoacrylates; D006540:Herbicides; D045322:Photosynthetic Reaction Center Complex Proteins; D045332:Photosystem II Protein Complex; D011725:Pyridines