title: Synthesis and biological evaluation of nitromethylene neonicotinoids based on the enhanced conjugation.
abstract: The neonicotinoids with a nitroconjugated system had excellent bioactivity, which could rival imidacloprid, and has been previously reported. However, the photodegradation and hydrolysis of this series of neonicotinoids was very quick according to our further investigation, which cannot be developed as a pesticide further. The approach to further enhance the conjugation was tried not only to increase the bioactivities but also to improve the stability in water and in the sun. A substituted phenyl group was introduced into the furan ring of compound 3. A total of 13 novel neonicotinoid analogues with a higher conjugation system were designed and synthesized. The target molecular structures have been confirmed on the basis of satisfactory analytical and spectral data. All compounds presented significant insecticidal activities on cowpea aphid ( Aphis craccivora ), cotton aphid ( Aphis gossypii ), and brown planthopper ( Nilaparvata lugens ). The stability test exhibited that the stability of novel analogues in water and under the mercury lamp has been improved significantly in comparison to compound 3.
authors.affiliation: Shanghai Key Laboratory of Chemistry Biology, Institute of Pesticides and Pharmaceuticals, East China University of Science and Technology , Shanghai 200237, People's Republic of China.
authors.forename: Siyuan
authors.initials: S
authors.lastname: Lu
authors.forename: Yingying
authors.initials: Y
authors.lastname: Zhuang
authors.forename: Ningbo
authors.initials: N
authors.lastname: Wu
authors.forename: Yue
authors.initials: Y
authors.lastname: Feng
authors.forename: Jiagao
authors.initials: J
authors.lastname: Cheng
authors.forename: Zhong
authors.initials: Z
authors.lastname: Li
authors.forename: Jie
authors.initials: J
authors.lastname: Chen
authors.forename: Jing
authors.initials: J
authors.lastname: Yuan
authors.forename: Xiaoyong
authors.initials: X
authors.lastname: Xu
mesh_terms: D000691:Anabasine / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D007313:Insecta / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure
chemical_list: D007306:Insecticides; D000691:Anabasine