Synthesis and herbicidal activity of diphenyl ether derivatives containing unsaturated carboxylates.

J Agric Food Chem

State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Research Institute of Chemical Industry Co. Ltd., Shenyang 110021, People's Republic of China.

Published: November 2011

AI Article Synopsis

  • A novel series of diphenyl ether derivatives with unsaturated carboxylates was created and their structures confirmed through nuclear magnetic resonance and elemental analysis.
  • The compounds 5b and 5c showed effective herbicidal activity against velvetleaf at a concentration of 30-40 g/hm².
  • Among the unsaturated carboxylates, 4-ethoxy-4-oxobutenyl 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoate (5b) was highlighted as the most promising candidate due to its strong inhibitory effect on protoporphyrinogen IX oxidase and selective herbicidal activity against certain broadleaf weeds

Article Abstract

A series of novel diphenyl ether derivatives containing unsaturated carboxylates were designed and synthesized. Their structures were identified by (1)H nuclear magnetic resonance and elemental analyses. The bioassays indicated that the compounds 5b and 5c exhibited good herbicidal activities against velvetleaf at a concentration of 30-40 g/hm(2). The relationship between structure and herbicidal activity was also discussed. Among unsaturated carboxylates group, butenoate is the most promising one. Amonst them, 4-ethoxy-4-oxobutenyl 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoate 5b was identified as the most promising candidate due to its high protoporphyrinogen IX oxidase inhibition effect (pI(50) = 6.64) and good herbicidal activity against broadleaf weeds with selectivity to soybean and low toxicity to mammals.

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http://dx.doi.org/10.1021/jf2039444DOI Listing

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