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Open AccessArticle

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

by 1,2, 1,2, 1,2, 1,2, 1,2, 1,2,* and 1,2,*
1
State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources, South China Agricultural University, Guangzhou 510642, China
2
Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, South China Agricultural University, Guangzhou 510642, China
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(4), 778; https://doi.org/10.3390/molecules23040778
Received: 8 February 2018 / Revised: 15 March 2018 / Accepted: 21 March 2018 / Published: 28 March 2018
(This article belongs to the Section Chemical Biology)
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. View Full-Text
Keywords: phloem-mobile pesticides; fipronil; passive diffusion; amino acid transporter phloem-mobile pesticides; fipronil; passive diffusion; amino acid transporter
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MDPI and ACS Style

Sheng, Q.; Liu, X.; Xie, Y.; Lin, F.; Zhang, Z.; Zhao, C.; Xu, H. Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism. Molecules 2018, 23, 778. https://doi.org/10.3390/molecules23040778

AMA Style

Sheng Q, Liu X, Xie Y, Lin F, Zhang Z, Zhao C, Xu H. Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism. Molecules. 2018; 23(4):778. https://doi.org/10.3390/molecules23040778

Chicago/Turabian Style

Sheng, Qingqing; Liu, Xinxin; Xie, Yun; Lin, Fei; Zhang, Zhixiang; Zhao, Chen; Xu, Hanhong. 2018. "Synthesis of Novel Amino Acid–Fipronil Conjugates and Study on Their Phloem Loading Mechanism" Molecules 23, no. 4: 778. https://doi.org/10.3390/molecules23040778

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