title: Synthesis and herbicidal activity evaluation of novel α-amino phosphonate derivatives containing a uracil moiety.
abstract: A series of novel α-amino phosphonate derivatives containing a uracil moiety 3a-3l were designed and synthesized by a Lewis acid (magnesium perchlorate) catalyzed the Kabachnik-Fields reaction. The bioassays {in vitro, in vivo [Glass House 1 (GH1) and Glass House 2 (GH2)]} showed that most of compounds 3 exhibited excellent and selective herbicidal activities; for example, in GH1 test, compounds 3b, 3d, 3f, 3h and 3j showed excellent and wide spectrum herbicidal activities at the dose of 1000 g/ha, and compounds 3b and 3j exhibited 100% inhibition activities against the four plants in both post- and pre-emergence treatments. Moreover, most of compounds 3 showed higher inhibition against Amaranthus retroflexus and Digitaria sanguinalis than Glyphosate did in pre-emergence treatment. In GH2 test, the four compounds (3b, 3d, 3h and 3j) exhibited 100% inhibition against Solanum nigrum, Amaranthus retroflexus and Ipomoea hederacea in post-emergence treatment and displayed 100% inhibition against Solanum nigrum, Amaranthus retroflexus in pre-emergence treatment at the rate of 250 g/ha, and compound 3b showed the best and broad spectrum herbicidal activities against the six test plants. However, the four compounds displayed weaker herbicidal activities against Lolium perenne and Echinochloa crus-galli than the other four plants at the rate of 250 g/ha in both pre- and post-emergence treatments. So, compounds 3 can be used as a lead compound for further structure optimization for developing potential selective herbicidal agent. Their preliminary structure-activity relationships were also investigated.
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People's Republic of China.
authors.forename: Jian-yi
authors.initials: JY
authors.lastname: Che
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People's Republic of China.
authors.forename: Xiao-yun
authors.initials: XY
authors.lastname: Xu
authors.affiliation: College of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201, People's Republic of China.
authors.forename: Zi-long
authors.initials: ZL
authors.lastname: Tang
authors.affiliation: Syngenta Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK.
authors.forename: Yu-cheng
authors.initials: YC
authors.lastname: Gu
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People's Republic of China. Electronic address: chshidq@mail.ccnu.edu.cn.
authors.forename: De-qing
authors.initials: DQ
authors.lastname: Shi
mesh_terms: D027721:Amaranthus / Q000187:drug effects; D031746:Digitaria / Q000187:drug effects; D005998:Glycine / Q000031:analogs & derivatives / Q000633:toxicity; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D027741:Ipomoea / Q000187:drug effects; D010757:Phosphorous Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D032324:Solanum nigrum / Q000187:drug effects; D013329:Structure-Activity Relationship; D014498:Uracil / Q000737:chemistry*; D000097797:Glyphosate
chemical_list: D005998:Glycine; D006540:Herbicides; D010757:Phosphorous Acids; D014498:Uracil; D000097797:Glyphosate; C570063:phosphonic acid
keywords: Herbicidal activity; Structure–activity relationship; Uracil; α-Amino phosphonate