The chiral pyrethroid cycloprothrin: stereoisomer synthesis and separation and stereoselective insecticidal activity.
The synthesis and separation of the isomers of the pesticide cycloprothrin have been realized for the first time. Complete separation was achieved on a DAICEL CHIRALCEL OJ-H column (25 x 0.46 cm) for (1R, alpha*)-cycloprothrin isomers and on a DAICEL CHIRALCEL OD-H column (25 x 0.46 cm()) for (1S, alpha*)-cycloprothrin isomers. The insecticidal activity of (1R, alphaR)-cycloprothrin for the larvae of Mythimaseparata and Aphismedicagini was found to be about six times and four times higher, respectively, than that of racemic cycloprothrin.
Jiang
Biao
B
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China. jiamgb@mail.sioc.ac.cn
Wang
Hua
H
Fu
Qun-Mei
QM
Li
Zhu-Yi
ZY
D000818:Animals; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects; D007915:Lepidoptera / Q000187:drug effects / Q000254:growth & development; D009570:Nitriles / Q000138:chemical synthesis* / Q000302:isolation & purification* / Q000494:pharmacology; D011722:Pyrethrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D003521:Cyclopropanes; D007306:Insecticides; D009570:Nitriles; D011722:Pyrethrins; C528277:cycloprothrin