title: Synthesis and Herbicidal Activity of α-(Substituted Phenoxybutyryloxy or Valeryloxy)alkylphosphonates and 2-(Substituted Phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one.
abstract: On the basis of our work on the modification of alkylphosphonates 1, a series of α-(substituted phenoxybutyryloxy or valeryloxy)alkylphosphonates (4-5) and 2-(substituted phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one (6) were designed and synthesized. The bioassay results indicated that 14 of title compounds 4 exhibited significant postemergence herbicidal activity against velvetleaf, common amaranth, and false daisy at 150 g ai/ha. Compounds 5 were inactive against all tested weeds. Compounds 6 exhibited moderate to good inhibitory effect against the tested dicotyledonous weeds. Structure-activity relationship (SAR) analyses showed that the length of the carbon chain as linking bridge had a great effect on the herbicidal activity. Broad-spectrum tests of compounds 4-1, 4-2, 4-9, 4-30, and 4-36 were carried out at 75 g ai/ha. Especially, 4-1 exhibited 100% inhibition activity against the tested dicotyledonous weeds, which was higher than that of glyphosate.
authors.affiliation: College of Chemistry, Central China Normal University ; Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, 152 Luoyu Road, Wuhan 430079, People's Republic of China.|Xi'an Modern Chemistry Research Institute , Xi'an 710000, People's Republic of China.
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.affiliation: College of Chemistry, Central China Normal University ; Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, 152 Luoyu Road, Wuhan 430079, People's Republic of China.
authors.forename: Sha-Sha
authors.initials: SS
authors.lastname: Zhang
authors.affiliation: College of Chemistry, Central China Normal University ; Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, 152 Luoyu Road, Wuhan 430079, People's Republic of China.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Zhou
authors.affiliation: College of Chemistry, Central China Normal University ; Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, 152 Luoyu Road, Wuhan 430079, People's Republic of China.
authors.forename: Hao
authors.initials: H
authors.lastname: Peng
authors.affiliation: College of Chemistry, Central China Normal University ; Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, 152 Luoyu Road, Wuhan 430079, People's Republic of China.
authors.forename: Hong-Wu
authors.initials: HW
authors.lastname: He
authors.affiliation: Tai'an Academy of Agricultural Sciences , Tai'an 271000, People's Republic of China.
authors.forename: Xing-Tao
authors.initials: XT
authors.lastname: Lu
mesh_terms: D027721:Amaranthus / Q000187:drug effects / Q000254:growth & development; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D057685:Plant Weeds / Q000187:drug effects / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: D006540:Herbicides
keywords: crop selectivity; herbicide; modification; phosphonate; structure−activity relationship; synthesis