title: Synthesis and Biological Activity Evaluation of Novel α-Amino Phosphonate Derivatives Containing a Pyrimidinyl Moiety as Potential Herbicidal Agents.
abstract: To find novel high-activity and low-toxicity herbicide lead compounds with novel herbicidal mode of action, series of novel α-amino phosphonate derivatives containing a pyrimidinyl moiety, I, II, III, and IV, were designed and synthesized by Lewis acid (magnesium perchlorate) catalyzed Mannich-type reaction of aldehydes, amines, and phosphites. Their structures were clearly identified by spectroscopy data (IR, (1)H NMR, (31)P NMR, EI-MS) and elemental analyses. The bioassay [in vitro, in vivo (GH1 and GH2)] showed that most compounds I exhibited good herbicidal activities; for example, the activities of compounds Ib, Ic, Ig, Ii, Ik, and Im were as good as the positive control herbicides (acetochlor, atrazine, mesotrione, and glyphosate). However, their structural isomers II and III and analogues IV did not display any herbicidal activities in vivo, although some of them possessed selective inhibitory activity against Arabidopsis thaliana in vitro. Interestingly, it was found that compounds IVs, IVt, and IVl showed selective insecticidal activities against Aphis species or Plutella xylostella, respectively. Their preliminary herbicidal mode of action and structure-activity relationships were also studied.
authors.affiliation: †Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, Hubei, People's Republic of China.
authors.forename: Jin-Long
authors.initials: JL
authors.lastname: Chen
authors.affiliation: †Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, Hubei, People's Republic of China.
authors.forename: Wu
authors.initials: W
authors.lastname: Tang
authors.affiliation: †Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, Hubei, 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 430079, Hubei, People's Republic of China.
authors.forename: Kai
authors.initials: K
authors.lastname: Chen
authors.affiliation: †Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, Hubei, People's Republic of China.
authors.forename: Gang
authors.initials: G
authors.lastname: Yan
authors.affiliation: §Syngenta Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, United Kingdom.
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 430079, Hubei, People's Republic of China.
authors.forename: De-Qing
authors.initials: DQ
authors.lastname: Shi
mesh_terms: D006540:Herbicides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D057685:Plant Weeds / Q000187:drug effects; D011743:Pyrimidines / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D006540:Herbicides; D063065:Organophosphonates; D011743:Pyrimidines
keywords: herbicidal activity; insecticidal activity; pyrimidine; α-amino phosphonate