农药学学报2026，Vol.28Issue(1)：116-127,12.DOI:10.16801/j.issn.1008-7303.2025.0101
新型1,3-二苯基脲类化合物的合成及其对福寿螺的杀灭活性
Synthesis of novel 1,3-diphenylurea derivatives and their molluscicidal activity against Pomacea canaliculata
摘要
Abstract
Pomacea canaliculata is a typical invasive alien species in southern China.Due to its strong adaptability and fecundity,it causes crop yield reduction and threatens food security.Therefore,the development of environmentally friendly molluscicides against P.canaliculata and the exploration of their action mechanisms are urgent needs for the prevention and control of invasive alien species at present.In this study,aniline and isocyanate derivatives were used as starting materials,and 10 novel 1,3-diphenylurea compounds(N-F-3a to N-F-3e and N-L-6a to N-L-6e)were synthesized via directed nucleophilic addition reaction between aniline and isocyanate derivatives.Their molluscicidal activity was evaluated by laboratory immersion toxicity tests;the changes in tissue morphology were observed by hematoxylin-eosin staining(H&E);and the action mechanisms were explored by multiple methods including enzyme activity assay and ligand-protein molecular docking.The results showed that compounds N-F-3a,N-F-3b,and N-L-6a to N-L-6c exhibited excellent molluscicidal activity against P.canaliculata,with a mortality rate>79.2%at 10 mg/L.Among them,compound N-F-3a showed the best activity:the mortality rate of P.canaliculata reached 100%within 72 h at 5 mg/L;the survival rate of carp larvae was 83.3%after 72 h of exposure at 20 mg/L,indicating a safer profile than the commercial molluscicide niclosamide.The results of H&E indicated that compound N-F-3a could cause significant hepatopancreas damage to P.canaliculata,which was an important factor leading to the death of P.canaliculata.Molecular docking calculations revealed that compound N-F-3a bound to phosphofructokinase through multiple interactions including hydrogen bonds,hydrophobic interactions,and π-π stacking,with a binding energy of-8.40 kcal/mol,which was lower than that of N-F-3d(-8.04 kcal/mol).This result was consistent with the molluscicidal activity data,which assisted in verifying the molluscicidal mechanism of compound N-F-3a against P.canaliculata.In conclusion,compound N-F-3a exhibits excellent molluscicidal efficacy against P.canaliculata and good biosafety,and is thus represents a promising candidate for developing novel molluscicide for P.canaliculata control.关键词
福寿螺/灭螺活性/1,3-二苯基脲类化合物合成/灭螺机制/分子对接Key words
Pomacea canaliculata/molluscicidal activity/1,3-diphenylurea derivatives/molluscicidal mechanism/molecular docking分类
农业科技引用本文复制引用
王梦军,普尚杰,江萍,杨芸如,叶王飞,姜治国,周莹..新型1,3-二苯基脲类化合物的合成及其对福寿螺的杀灭活性[J].农药学学报,2026,28(1):116-127,12.基金项目
国家自然科学基金项目(No.22367023) （No.22367023）
云南省重大科技专项计划(No.202402AE0900069) （No.202402AE0900069）
云南大学省级大学生创新创业训练项目(No.S202310673241) （No.S202310673241）
云南大学"绿色农药研究"产教融合研究生联合培养基地项目. Supported by National Natural Science Foundation of China(No.22367023) （No.22367023）
Major Science and Technology Special Project of Yunnan Province(No.202402AE0900069) （No.202402AE0900069）
Provincial-Level Innovation and Entrepreneurship Training Program for Undergraduate Students of Yunnan University(No.S202310673241) （No.S202310673241）
Yunnan University"Green Pesticide Research"Industry-Education Integration Graduate Student Joint Training Base Program. （）
