title: An efficient synthesis method targeted to a novel aziridine derivative of p-menthane from turpentine and its herbicidal activity.
abstract: A novel aziridine compound N-acetyl-1,2-azacyclo-p-menthane d was synthesised using turpentine as raw material and characterised by FT-IR,1H NMR,13C NMR, ESI+-MS and HRMS. The pre-emergence herbicidal activities of d and its synthetic intermediates cis- and trans-N,N'-diacetyl-p-menthane-1,8-diamine (b2 and b1) were determined. The result showed that d exhibited much higher herbicidal activities against annual ryegrass, Digitaria sanguinalis and Ixeris denticulate than b2 and b1. The IC50of d against the root and shoot growth of these three plants were lower than 1 mmol L-1. In contrast, the IC50of b1 and b2 against the root and shoot growth of these plants were more than 10 mmol L-1.
authors.affiliation: a Institute of Chemical Industry of Forest Products , CAF , Nanjing , China.|b Key and Open Lab. on Forest Chemical Engineering , SFA , Nanjing , China.|c Research Institute of Forestry New Technology , CAF , Beijing , China.|d College of Material Science and Technology , Bejing Forestry University , Beijing , China.
authors.forename: Shou-Ji
authors.initials: SJ
authors.lastname: Zhu
authors.affiliation: a Institute of Chemical Industry of Forest Products , CAF , Nanjing , China.|b Key and Open Lab. on Forest Chemical Engineering , SFA , Nanjing , China.|c Research Institute of Forestry New Technology , CAF , Beijing , China.
authors.forename: Shi-Chao
authors.initials: SC
authors.lastname: Xu
authors.affiliation: a Institute of Chemical Industry of Forest Products , CAF , Nanjing , China.|b Key and Open Lab. on Forest Chemical Engineering , SFA , Nanjing , China.|c Research Institute of Forestry New Technology , CAF , Beijing , China.
authors.forename: Zhen-Dong
authors.initials: ZD
authors.lastname: Zhao
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis* / Q000494:pharmacology*; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008610:Menthol / Q000031:analogs & derivatives / Q000737:chemistry; D010944:Plants / Q000187:drug effects; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship; D014425:Turpentine / Q000737:chemistry*
chemical_list: D001388:Aziridines; D006540:Herbicides; D008610:Menthol; C033132:aziridine; D014425:Turpentine
keywords: 2-azacyclo-p-menthane; N-acetyl-1; aziridine; botanical herbicides; herbicidal activity; p-menthane; turpentine