Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism

Autor: Qingqing Sheng, Xinxin Liu, Yun Xie, Fei Lin, Zhixiang Zhang, Chen Zhao, Hanhong Xu
Jazyk: angličtina
Rok vydání: 2018
Předmět:
Zdroj: Molecules, Vol 23, Iss 4, p 778 (2018)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules23040778
Popis: To develop a new pesticide with phloem mobility, a series of new amino acid–fipronil conjugates were designed and synthesized based on derivatization at the 3-position of the pyrazole ring of fipronil. Experiments using a Ricinus communis seedling system showed that all tested conjugates were phloem mobile except for the isoleucine–fipronil conjugate, and that the serine–fipronil conjugate (4g) exhibited the highest concentration in phloem sap (52.00 ± 5.80 μM). According to prediction with log Cf values and uptake experiments with Xenopus oocytes, the phloem loading process of conjugate 4g involved both passive diffusion and an active carrier system (RcANT15). In particular, compared with for a previously reported glycinergic–fipronil conjugate (GlyF), passive diffusion played a more important role for conjugate 4g in the enhancement of phloem mobility. This study suggests that associating a nutrient at a different position of an existing pesticide structure could still be effective in obtaining phloem-mobile derivatives, but the distinct physicochemical properties of resultant conjugates may lead to different phloem loading mechanisms.
Databáze: Directory of Open Access Journals
Nepřihlášeným uživatelům se plný text nezobrazuje