PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
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2025
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IF 4
Shiling Liu,Siying Qin,Tengfei Zhang,Heng Zhang,Junqi Zhu,Xiaoli Li,Yuanfu Li,Feng Zhao
Flusulfinam is a novel chiral amide herbicide widely used for controlling annual weeds in rice paddies. However, the mechanism underlying their enantioselective herbicidal activity remain unclear. Herein, it was found that flusulfinam enantiomers, similar to typical HPPD inhibitor mesotrione, reduced chlorophyll a nd carotenoid levels, decreased HPPD enzyme activity, and upregulated gene expression. Additionally, homogentisate supplementation alleviated the bleaching symptoms caused by flusulfinam and all these results validate that flusulfinam is indeed an HPPD inhibitor. To further investigate the mechanism of enantioselectivity, molecular docking was used and showed that R -flusulfinam (−6.55 kcal/mol) had higher binding energy than S- flusulfinam (−5.60 kcal/mol), due to more stable hydrogen bonds with Gln293. After mutating Gln293 to His, the IC 50 values for R -flusulfinam and S -flusulfinam on Mut Q293H were 0.73 mg/L and 0.11 mg/L, respectively, indicating swapped enantioselective inhibition compared to At HPPD, with IC 50 values of 0.52 mg/L and 1.93 mg/L, respectively. The Microscale Thermophoresis assay further revealed that the dissociation constant (Kd) for Mut Q293H with R -flusulfinam was 20.40 ± 4.19 μM, similar to the Kd value of 15.63 ± 4.51 μM for S -flusulfinam. The findings reveal that mutation of the Gln293 residue in the At HPPD enzyme significantly altered its enantioselective inhibition by flusulfinam. This study is the first to verify the mode of action of flusulfinam and identifies that Gln293 may play a key role in flusulfinam enantioselectivity in the At HPPD, laying the foundation for future HPPD inhibitor development based on flusulfinam.
研究领域:
植物生理学
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分子生物学
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农药科学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF HAZARDOUS MATERIALS
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2025
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IF 11.3
Shiling Liu,Xiaoli Li,Siying Qin,Heng Zhang,Tengfei Zhang,Junqi Zhu,Lu Lin,Lei Lian,Fayang Xie,Huihua Tan,Feng Zhao
Flusulfinam, a novel chiral herbicide, demonstrates effective weed control in paddy fields. Nevertheless, a comprehensive investigation into its environmental fate in paddy systems, particularly at the enantiomeric level, remains deficient. Herein, paddy water–sediment microcosms were constructed across four sites to explore the enantiomeric behavior of flusulfinam. Enantioselective environmental behavior results show S- flusulfinam was found to preferentially accumulate in sediment, while R- flusulfinam showed preferential degradation in water and the overall system. Following this, the metabolic pathway of flusulfinam in the microcosms was also proposed. Eight metabolites were identified for the first time, and the synthesis and quantification of main metabolites M299 and M100 further substantiated the proposed flusulfinam metabolic pathways. In addition, enantioselective of R -M299 was also found in the Anhui microcosms. As predicted by Toxicity Estimation Software Tool, acute toxicity assessments revealed that M299 and M100 exhibit lower toxicity toward Danio rerio larvae and Selenastrum capricornutumwere compared to flusulfinam. Then, Illumina sequencing revealed that the degradation of flusulfanam had a significant impact on the abundance of key microbial genera, including Anaeromyxobacter, Nitrospira, Reyranella, and Sphingomonas . Overall, this study offers novel insights into the enantioselective fate of flusulfinam in paddy water–sediment ecosystems, provides a valuable reference for the assessment of environmental and ecological risks associated with flusulfinam. Finally, the R -flusulfinam is considered the safer enantiomer, as evidenced by its preferential degradation in microcosms systems and our prior research highlighting the high efficacy and low toxicity characteristic of R -flusulfinam.
研究领域:
环境科学
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生态学
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农业科学
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产品关联
DOI
PubMed
高影响因子
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
·
2026
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IF 4.8
Yu Wang,Junqi Zhu,Mingdong Deng,Huijin Lin,Huanyu Zhou,Wenyu Dai,Ya Zhou,Tengfei Zhang,Yanmei Liu,Huihua Tan,Feng Zhao
Flusulfinam (FLU) is a novel HPPD-inhibiting herbicide that exhibits excellent efficacy against a broad spectrum of weeds in paddy fields, with particular activity against grasses and sedges. However, its phytotoxicity to crops other than rice restricts its application scenarios. This study demonstrates that the safener cyprosulfamide (CSA) could effectively alleviate FLU-induced phytotoxicity in maize, without compromising its high efficacy against weeds in maize field. Specifically, CSA alleviates FLU-induced oxidative stress and photosynthetic damage in maize. Moreover, CSA could accelerate FLU dissipation in maize, reducing its half-life from 0.94 d to 0.87 d. Transcriptomic and qRT-PCR analyses further revealed that CSA significantly upregulated detoxification-associated P450 genes. CYP72A28 and CYP94B12 were identified as candidate CYP450 genes potentially associated with FLU detoxification based on their transcriptional responses to CSA co-application; meanwhile, total CYP450 content was significantly increased ( p < 0.05). Our findings highlight the FLU + CSA combination as a safe and efficient formulation for sustainable weed control in maize fields.
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DOI
高影响因子
Emerging Contaminants
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2026
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IF 8.2
Ling Wu,Mengting Liang,Yanxi Sun,Shanshan Fu,Yuping Zhang
Flusulfinam, a novel chiral herbicide, has attracted considerable attention because of its high efficacy against common paddy weeds and its favorable crop safety profile. However, information regarding its enantioselective toxicity toward aquatic organisms remains scarce. In this study, single-crystal X-ray diffraction was employed to determine the absolute configurations of flusulfinam enantiomers. The results indicated that the enantiomers can stably persist in the aquatic environment of Daphnia magna , with no detectable configurational transformation or degradation. Both racemic flusulfinam and its individual enantiomers exhibited low toxicity to D. magna . At sublethal concentrations (0.95 and 9.5 mg/L), R-flusulfinam and S-flusulfinam induced short-term inhibition (24 h) followed by long-term stimulation (48–72 h) of swimming distance and speed in D. magna . Oxidative stress assessments showed increased activities of superoxide dismutase (SOD) and catalase (CAT), with R-flusulfinam producing more pronounced effects than S-flusulfinam. Metabolomic analyzes further revealed that both enantiomers interfered with nucleotide and purine metabolism in D. magna , while R-flusulfinam caused more severe metabolic disturbances. Overall, these findings demonstrate that R-flusulfinam exhibits greater toxicity to D. magna than S-flusulfinam, providing important insights for the environmental risk assessment of flusulfinam.
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DOI
高影响因子
危险品化学品经营许可证（带存储）