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Imidacloprid 와 그 유도체들의 살충활성에 미치는 3 - N - 치환기 ( R ) 의 영향
성낙도(Nack Do Sung),강문성(Moon Sung Kang),장해성(Hae Sung Jang),김대황(Dae Whang Kim) 한국응용생명화학회 1996 Applied Biological Chemistry (Appl Biol Chem) Vol.39 No.2
Imidacloprid and a series of the related compounds were synthesized, and influence of 3-N substituents(R) on the insecticidal activities against Brown plant hopper(Nilaparvata lugens) and Green peach aphid(Myzus persicae) were examined quantitatively from the structure-activities relationships(SAR) techniques. The results indicated that the molecular hydrophobicity(π) and inductive substituent constant(σ^*) of substituents(R) at 3-nitrogen position on the imidazolidine ring were important factors. Variations in the potency were parabolically related to the both constants. In case of Brown plant hopper, optimum value of π constant was 0.52, whereas the value of σ^* constant against Green peach aphid was 1.17, respectively. Among them, the strong electron withdrawing groups(σ^*$gt;0) such as methyl and benzenesulfonyl group(7 & 8) showed lower insecticidal activity and non-substituted, 1(imidacloprid) showed the best insecticidal activity. It seems that the intramolecular associated(H-bond) form between 2-N-nitro group and 3-imid group may contribute to the higher insecticidal activity to the both sucking insects. And in aqueous solution, 1 showed higher residual activity below pH 6.0, and the half-life(T_½) was about 6 month at pH 7.0 (ca. k_(obs) : 5×10^(-8) sec.^(-1)) and 45℃.
살충성 Imidacloprid의 가수분해 반응 메카니즘
성낙도,유성재,강문성 ( Nack Do Sung,Seong Jae Yu,Moon Sung Kang ) 한국응용생명화학회 1997 Applied Biological Chemistry (Appl Biol Chem) Vol.40 No.1
The rate of hydrolysis of insecticidal 1-(6-chloro-3-pyridylmethyl)-2-nitro-iminoimidazolidine (common name; imidacloprid) have been investigated in 15%(v/v) aqueous dioxane at 45℃. From the kinetics and non-kinetics data such as pH-effect, solvent effect(m=0.04, n=0.30 & m≪ℓ), thermodynamic parameter(△H^*=16.14㎉·㏖^(-1) & △S^*=-0.03e.u.), rate equation (k_(obs.)=4.56×10^(-3)[OH^-]) and analysis of hydrolysis product, 1-(6-chloro-3-pyridylmethyl-2)-imidazolidinon, the hydrolysis mechanism of imidacloprid is proposed that the specific base catalyzed hydrolysis(k_(OH)) through nucleophilic addition-elimination (Ad_N-E) mechanism proceed via intermediate, 1-(6-chloro-3-pyridylmethyl)-2-hydroxy-2-imidazolidinylisonitraminate (Ⅰ) and β-3-(6-chloro-3-pyridylmethyl)aminoethyl-1-nitrourea(Ⅲ). And the half-life(t½) of hydrolytic degradation at pH 8.0 and 45℃ was about 4.5 months.