Chloronicotinyl 유도체의 합성 및 생물활성 검정

Synthesis and biological activities of Chloronicotinyl derivatives

Chloronicotinyl 유도체의 기본 골격인 3-pyridylmethylamine의 amine기를 phosphite group으로 치환하여 chloronicotinyl 유도체를 합성하였고, 이들의 살충활성과 살균활성을 확인하였다. 살충활성 검정 결과, 500 ppm 에서 phosphonate에 methyl기와 butyl기가 치환된 compound 4와 2개의 butyl, 2,2,2-trifluorotehtyl, 2-ethylhexyl, phenyl기가 치환된 compound 5, 6, 7, 8이 벼멸구에 대해서 90%의 살충활성을 나타내었다. 그러나 이들 화합물들은 배추좀나방과 두점박이응애에 대해서는 낮은 살충활성을 나타내었으며, phosphonate에 halogen이나 heterocycle이 치환된 compound $10{\sim}21$에서도 벼멸구, 배추좀나방, 담배거세미나방, 두점박이응애, 복숭아혹진딧물에 대하여 거의 살충활성을 나타내지 않았다. Chloronicotinyl 유도체의 벼도열병균, 벼문고병균, 오이잿빛 곰팡이병균, 토마토역병균, 밀녹병균, 보리흰가루병균에 대한 살균활성을 검정한 결과, 10 ppm에서 phosphonate에 butyl기와 4-nitrophenyl기가 치환된 compound 10이 벼도열병균에 대해 86%의 살균활성을 보였다. 인 함유 chloronicotinyl 유도체들 중 일부가 높은 살균활성을 나타낸다는 것은 이 유도체들이 신규 살균제로 개발될 가능성이 있다는 것을 시사하고 있다.

Chloronicotinyl derivatives were synthesized by substitution of amino in 3-pyridylmethylamine with phosphite groups and their insecticidal and fungicidal activities were determined. At 500 ppm, compound 4 with methyl and butyl group in phosphonate and compound 5, 6, 7, and 8 with two butyl, 2,2,2-trifluorotehtyl, 2-ethylhexyl, phenyl, respectively, in phosphonate showed 90% insecticidal activities against brown plant-hopper (Nilaparvate lugens). These compounds showed, however, poor insecticidal activities against diamond-back moth (Plutella xylostella) and two-spotted spider mite (Tetranychus urticae) (<65%), suggesting that insecticidal activity of chloronicotinyl derivatives containing phosphorus moieties are species-dependent. Newly synthesized chloronicotinyl derivatives with halogen and/or heterocycle (compound $10{\sim}21$) did not show insecticidal activities. We also determined fungicidal activity of the synthesized chloronicotinyl derivatives against rice sheath blight (Pyricularia grisea), cucumber gray mold (Bortytis cinerea), tomato late blight (Phytophthora infestans), wheat leaf rust (Puccinia recondita), and barley powdery mildew (Erysiphe graminis). Compound 10 with butyl and 4-nitrophenyl in phosphonate at 10 ppm showed 85% fungicidal activity against rice blast, suggesting that chloronicotinyl derivatives containing phosphorus moieties could be developed as a fungicidal agent of a novel chemical structure.