Synthesis of quinolactacide via an acyl migration reaction and dehydrogenation with manganese dioxide, and its insecticidal activities.
Quinolactacide isolated from Penicillium citrinum F 1539 was synthesized and evaluated for its insecticidal activities. The key steps of the total synthesis were an acyl migration reaction of the enol ester intermediate and dehydrogenation of tetrahydroquinolactacide with manganese dioxide. The synthesized quinolactacide showed 100% and 42% mortality against the green peach aphid (Myzus persicae) and diamondback moth (Plutella xylostella) at 500 ppm, respectively.
Abe
Masaki
M
Naruto Research Center, Otsuka Chemical Co., Ltd, Tokushima, Japan. mabe@otsukac.co.jp
Imai
Tetsuya
T
Ishii
Naoki
N
Usui
Makio
M
D000215:Acylation; D000818:Animals; D001042:Aphids / Q000187:drug effects; D006865:Hydrogenation; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017895:Manganese Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects; D010087:Oxides / Q000737:chemistry*; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D007306:Insecticides; D017895:Manganese Compounds; D010087:Oxides; D015363:Quinolones; C504852:quinolactacide; C016552:manganese dioxide