Enantioselective hydrolyzation and photolyzation of dufulin in water.
Enantioselective hydrolyzation and photolyzation of dufulin in water.
复制标题
dufulin在水中的对映选择性水解和光解。
DOI：
10.1186/1752-153x-7-86
复制
发表时间：
2013-05-16
影响因子：
--
通讯作者：
Song B
中科院分区：
文献类型：
--
作者：
Zhang K;Hu D;Zhu H;Yang J;Wu J;He M;Jin L;Yang S;Song B
毒氟灵是一种新型高效抗病毒剂，能激活植物的系统获得抗性。该化合物在我国广泛用于烟草、蔬菜和水稻病毒病的防治。毒福林可以治疗烟草花叶病毒和黄瓜花叶病毒。但毒福林的手性分离和残留检测技术因其高的对映选择性和高的控制成本而一直处于研究阶段。抗病毒化合物的对映选择性是研究手性农药对环境影响时应考虑的重要因素。毒氟磷在水中的对映体选择性降解是农药科学研究的一个重要课题。利用圆二色谱法确定了毒福林对映体的构型。采用正相高效液相色谱法，以直链淀粉-三（3，5-二甲基苯基氨基甲酸酯）手性固定相为分离柱，对S-（+）-dufulin和R-（-）-dufulin对映体进行了分离和鉴定。rac-dufulin外消旋体及其分离的对映体的降解符合一级反应动力学，并表现出可接受的线性。与S-（+）-dufulin相比，rac-dufulin的对映选择性光解允许R-（-）-dufulin更快地降解。然而，S-（+）-dufulin的水解速度比其对映体快。水样中毒氟磷的光解和水解均符合一级动力学，线性关系良好（R2>0.66）。在水样中观察到R-（-）-对映体的优先光解。此外，S-（+）-对映体比其对映体水解得更快。
Dufulin is a novel, highly effective antiviral agent that activatives systemic acquired resistance of plants. This compound is widely used in China to prevent and control viral diseases in tobacco, vegetable and rice. Dufulin can treat plants infected by the tobacco mosaic virus and the cucumber mosaic virus. However, the achiral analysis and residue determination of dufulin remain underdeveloped because of its high enantioselectivity rates and high control costs. The enantioselectivity of an antiviral compound is an important factor that should be considered when studying the effect of chiral pesticides on the environment. The enantioselective degradation of dufulin in water remains an important objective in pesticide science. The configuration of dufulin enantiomers was determined in this study based on its circular dichroism spectra. The S-(+)-dufulin and R-(−)-dufulin enantiomers were separated and identified using an amylose tris-(3,5-dimethylphenylcarbamate) chiral column by normal phase high-performance liquid chromatography. The degradation of the rac-dufulin racemate and its separate enantiomers complied with first-order reaction kinetics and demonstrated acceptable linearity. The enantioselective photolysis of rac-dufulin allowed for the faster degradation of R-(−)-dufulin, as compared with S-(+)-dufulin. However, S-(+)-dufulin was hydrolyzed faster than its antipode. The photolysation and hydrolyzation of dufulin in water samples normally complied with the first-order kinetics and demonstrated acceptable linearity (R2>0.66). A preferential photolysation of the R-(−)-enantiomer was observed in water samples. Moreover, the S-(+)-enantiomer was hydrolyzed faster than its antipode.