The Korean Journal of Pesticide Science (농약과학회지)

The Korean Society of Pesticide Science (한국농약과학회)
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Synthesis and biological activities of organophosphate and carbamate compounds derived from 2-hydroxy-5-nitrobenzoic acid and 3-hydroxy-4-nitrobenzoic acid

2-Hydroxy-5-nitrobenzoic acid와 3-hydroxy-4-nitrobenzoic acid의 유기인계와 카바메이트계 유도체 합성 및 생물활성

  • Choi, Dal-Soon (Botanical Pesticide Lab., National Institute of Agricultural Science and Technology, RDA) ;
  • Kyung, Suk-Hun (Department of Agricultural Chemistry, Kun-Kuk University) ;
  • Kwon, Oh-Kyung (Botanical Pesticide Lab., National Institute of Agricultural Science and Technology, RDA) ;
  • Seong, Ki-Seog (Botanical Pesticide Lab., National Institute of Agricultural Science and Technology, RDA)
  • Published : 1998.04.30
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Abstract

Salicylic acid and 3-hydroxy benzoic acid are nitrated and esterified with some alcohols. Five phosphate and six carbamate compounds of alkyl-5-nitrosalicylate and alkyl-3-hydroxy-4-nitrobenzoate are synthesized by reacting alkyl-5-nitrosalicylate and alkyl-3-hydroxy-4-nitrobenzoate with diethyl-chlorophosphate and methyl isocyanate. As the bioassay results of synthesized compounds on five insects and six pathogens, the brown planthopper (BPH, Nilaparvata lugens) mortality of O-(2-carbomethoxy-4-nitrophenyl) O,O-diethylphosphate and O-(2-nitro-5-carbo methoxyphenyl) O,O-diethylphosphate was 96%, while four compounds including O-(2-carbo-(2-chloroethoxy)-4-nitrophenyl) O,O-diethylphosphate showed more than 95% of fungicidal activity on rice blast.

버드나무 껍질중의 배당체인 salicin으로부터 유래된 salicylic acid와 그 유사화합물인 3-hydroxy benzoic acid의 질산화된 중간체를 출발물질로 하여 몇몇의 알콜과 에스테르화반응을 거쳐 유기인계 및 카바메이트계 화합물의 전구체를 합성하였다. 합성된 전구체의 수산기에 diethylchlorophosphate와 methyl isocyanate를 반응시켜 유기인계 및 카바메이트계 화합물 11종을 합성하였다. 합성된 화합물은 살충, 살균활성실험을 실시하였다. 유기인계 화합물의 벼멸구에 대한 활성은 500 ppm의 농도에서 O-(2-carbomethoxy-4-nitro phenyl) O,O-diethylphosphate 화합물이 96%의 살충력을 보였다. 반면 carbamate 화합물의 경우는 500ppm농도에서 살충력이 전혀 나타나지 않았다. 살균효과는 유기인계 화합물인 경우 도열병에 대해서 ester에 관계없이 250 ppm농도에서 95% 이상의 방제가를 나타냈으며, 그 이외의 병원균에서는 낮은 방제가를 보였다.

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