JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Yinglu Chen,Yitao Yan,Jie Chen,Ben Zheng,Youwei Jiang,Zhengzhong Kang,Jun Wu
Given the prevalence of the malignant weed Chinese Sprangletop (Leptochloa chinensis (L.) Nees) in rice fields, the development of novel herbicides against this weed has aroused wide interest. Here, we report a novel diphenyl ether-pyrimidine hybrid, DEP-5, serving as a systematic pre/postemergence herbicide candidate for broad-spectrum weed control in rice fields, specifically for L. chinensis. Notably, DEP-5 exhibits over 80% herbicidal activity against the resistant biotypes even at 37.5 g a.i./ha under greenhouse conditions and has complete control of L. chinensis at 150 g a.i./ha in the rice fields. We uncover that DEP-5 acts as a noncompetitive inhibitor of acetohydroxyacid synthase (AHAS) with an inhibition constant (Ki) of 39.4 μM. We propose that DEP-5 binds to AHAS in two hydrophobic-driven binding modes that differ from commercial AHAS inhibitors. Overall, these findings demonstrate that DEP-5 has great potential to be developed into a herbicide for L. chinensis control and inspire fresh concepts for novel AHAS-inhibiting herbicide design.
研究领域:
植物学
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农业科学
·
分子生物学
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DOI
PubMed
高影响因子
PEST MANAGEMENT SCIENCE
·
2021
·Vol. 78
·期 3
·1176-1186
·
IF 4.845
Ning Zhao,Minghao Jiang,Qi Li,Quan Gao,Jingxu Zhang,Min Liao,Haiqun Cao
BACKGROUND Chinese sprangletop ( Leptochloa chinensis (L.) Nees) is an invasive grass weed severely infesting rice fields across China. In October 2020, a suspected resistant Leptochloa chinensis population HFFD3 that survived the acetyl-CoA carboxylase (ACCase)-inhibiting herbicide cyhalofop-butyl applied at its field-recommended rate was collected from a rice field in Feidong County, Anhui Province, China. This study aimed to determine the resistance profile of HFFD3 to ACCase inhibitors and to investigate its mechanisms of resistance to cyhalofop-butyl. RESULTS Single-dose testing confirmed that HFFD3 had evolved resistance to cyhalofop-butyl. Two loci encoding plastidic ACCase were each amplified from the susceptible (S) and resistant (R, HFFD3) individual plants. Target gene sequencing and derived cleaved amplified polymorphic sequence assay revealed all the R plants carried a Trp-2027-Leu substitution in their ACCase1,2 copies. Dose–response bioassays revealed that HFFD3 was highly resistant to cyhalofop-butyl and exhibited cross-resistance to metamifop, fenoxaprop- P -ethyl, quizalofop- P -ethyl, and clethodim. Pre-treatment with piperonyl butoxide and 4-chloro-7-nitrobenzoxadiazole considerably reversed the resistance of the R plants to cyhalofop-butyl, by 23% and 43%, respectively. Liquid chromatography–tandem mass spectrometry analysis suggested the metabolic rates of cyhalofop-butyl were significantly faster in the R than in the S plants. CONCLUSION This study confirmed the first case of an arable weed species featuring cross-resistance to ACCase-inhibiting herbicides due to a novel Trp-2027-Leu mutation of ACCase . Target gene mutation and cytochrome P450s- and glutathione- S -transferases-involved enhanced metabolism may have simultaneously participated in the resistance of HFFD3 population to cyhalofop-butyl.
研究领域:
植物学
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遗传学
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农药科学
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产品关联
DOI
PubMed
高影响因子
PEST MANAGEMENT SCIENCE
·
2026
·
IF 4.2
Xiang Qu,Kaixiang Liu,Penglei Sun,Hailan Cui,Jingchao Chen,Haiyan Yu,Chaoxian Zhang,Xiangju Li
BACKGROUND Chinese sprangletop ( Leptochloa chinensis (L.) Nees), a dominant weed species in Chinese rice fields, poses a significant threat to rice yield and quality because of its increasing resistance to herbicides. In particular, resistance to cyhalofop-butyl (Cyb) has become a major concern in weed control. The mechanism by which the Asp-2078-Gly mutation confers resistance to acetyl-CoA carboxylase (ACCase) inhibitors in L . chinensis remains unclear. In this study, we collected Cyb-resistant L . chinensis populations from rice-growing regions and characterized their resistance mechanisms. RESULTS Through molecular analysis, we identified a resistant population harboring the Asp-2078-Gly mutation. Whole-plant dose–response experiments showed that the resistant (R) population exhibited varying levels of resistance compared with the susceptible (S) population: resistance indices values were 15.42 for FOP herbicides Cyb, 12.77 for metamifop, 11.50 for fenoxaprop-P-ethyl; 13.13 for the DIM herbicide clethodim; and 8.61 for the DEN herbicide pinoxaden. Quantitative real-time polymerase chain reaction (qRT-PCR) analysis revealed no significant difference in ACCase gene expression between the Asp-2078-Gly mutant and the susceptible (S) population, indicating that resistance to Cyb was not due to target enzyme overexpression. Furthermore, the resistance of the mutant was not alleviated by P450 or glutathione S -transferase inhibitors, suggesting non-metabolic mechanisms. CONCLUSION Structural analysis confirmed that the Asp-2078-Gly mutation induces significant conformational changes in the herbicide-binding pocket, which reduces herbicide sensitivity and confers resistance. This study elucidates the resistance mechanism conferred by the Asp-2078-Gly mutation in L . chinensis , providing valuable insights for managing herbicide-resistant weeds. © 2026 Society of Chemical Industry.
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DOI
PubMed
高影响因子
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
·
2026
·
IF 4.8
Minghao Jiang,Jingjing Ning,Junji Wang,Wei Hu,Penglei Sun,Ning Zhao,Haiqun Cao,Min Liao
Chinese sprangletop ( Leptochloa chinensis (L.) Nees) has emerged as a dominant grass weed in rice fields, representing a serious risk to crop productivity because of its rapidly increasing resistance to herbicides. A putative resistant population, MASHS7 (R), was collected from an imidazolinone-tolerant rice field, where it had survived applications of cyhalofop-butyl (CYB) and imazamox (IMA) at the field-recommended rates. Dose–response assays indicated that compared with the susceptible (S) population, the R population developed resistance to CYB (26.29-fold) and IMA (5.50-fold). Additionally, both the cytochrome P450 (P450) inhibitor malathion and the glutathione S -transferase (GST) inhibitor 4-chloro-7-nitro-1,2,3-benzoxadiazole (NBD-Cl) partially reversed the resistance of the R population to CYB and IMA. Target-site resistance mechanism analysis revealed that the R plants carried a Trp-to-Cys mutation at codon 1999 of ACCase , with no mutations in the ALS gene, and exhibited no overexpression of any target gene. Compared with the S plants, the R plants metabolized CYB, cyhalofop acid (CYA) and IMA faster. RNA sequencing analysis and quantitative real-time PCR (qPCR) validation confirmed that two P450s ( CYP709B2 and CYP81Q32b ) and one GST ( GST4 ) gene were constitutively upregulated in the R plants. Molecular docking results predicted favorable binding interactions of these enzymes with CYA and IMA.
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DOI
高影响因子
PEST MANAGEMENT SCIENCE
·
2025
·
IF 3.8
Guoqi Chen,Kai An,Jiahao Xue,Wei Deng,Zeyue Huang,Yang Xu
BACKGROUND Various mechanisms or factors may cause the wide infestation of herbicide-resistant weeds with different contributions, such as target-site resistance (TSR), non-target-site resistance (NTSR), hormesis, and dissemination of herbicide-resistant weeds. Here we tested this hypothesis in eastern China in Leptochloa chinensis , for which cyhalofop resistance is a major challenge to rice planting. RESULTS Our results revealed that 30% of the total 242 populations held high (10 < RI < 100) or very high resistance (RI > 100) to cyhalofop. Resistance increased from north to south, and from transplanted rice fields to direct-seeded rice fields. Six mutant types conferring TSR to cyhalofop were found in 89% sampled populations, with 18% carrying two types, 2% carrying three types, and another 2% carrying four types of mutations. W2027C was the most frequent TSR mutation, present in 47.3% of sampled populations, followed by I2041N (21.8%), W1999C (20%), L1818F (20%), W1999G (5.5%) and C2088R (1.8%). Non-target-site resistance linked with P450 monooxygenases (P450) and glutathione S-transferases (GST) were observed in 7% and 10% cyhalofop-resistant populations sampled. No significant correlation between genetic and geographic distances were observed among cyhalofop-resistant populations. Hormetic effects of cyhalofop to L. chinensis were evident in 13% of overall populations. CONCLUSIONS This study compared the contribution of different mechanisms towards herbicide resistance, revealed herbicide hormesis and revealed the distribution of resistance. Insights from this study could be important for weed management practices in other areas of the world. © 2025 Society of Chemical Industry.
研究领域:
植物学
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遗传学
·
农业科学
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产品关联
DOI
PubMed
高影响因子
PLANT PHYSIOLOGY AND BIOCHEMISTRY
·
2025
·
IF 5.7
Minghao Jiang,Xin Chen,Tianqiao He,Wei Hu,Ning Zhao,Min Liao,Haiqun Cao
Chinese sprangletop ( Leptochloa chinensis (L.) Nees) is among the most economically damaging and disruptive weeds found in rice fields across China, and it exhibits a high degree of cyhalofop-butyl resistance for the past few years. Here, a suspected cyhalofop-butyl-resistant population HFCH5 (R) was collected from a rice field and analyzed to explore the mechanistic basis for its resistance activity. Compared with the susceptible HFLY1 (S) population, this R population exhibited differing levels of resistance to four ACCase-inhibiting herbicides (cyhalofop-butyl (RI = 11.52), fenoxaprop- P -ethyl (RI = 11.05), metamifop (RI = 6.61), and clethodim (RI = 4.06)), although it did exhibit susceptibility to florpyrauxifen-benzyl, tripyrasulfone, pyraclonil, and anilofos. This cyhalofop-butyl resistance in R plants was not effectively mitigated by pre-treatment with the cytochrome P450 inhibitor piperonyl butoxide or the glutathione S-transferase inhibitor 4-chloro-7-nitrobenzoxadiazole. Further analyses of these R plants revealed the substitution of Trp-1999 (TGG) for a Gly residue (GGG) within the ACCase carboxyltransferase domain. When the wild-type and mutated forms of this ACCase protein were subjected to structural modeling while complexed with a range of herbicides with ACCase-inhibiting activity, this Trp-1999-Gly substitution was found to be associated with a slight decrease in the affinity of this protein for a series of ACCase-inhibiting herbicides. A dCAPS marker was developed to aid in the rapid detection of this Trp (TGG)-1999-Gly (GGG) mutation within L. chinensis . Notably, before or after four ACCase-inhibiting herbicides (cyhalofop-butyl, fenoxaprop- P -ethyl, metamifop and clethodim) treatment, ACCase gene expression level of the R plants was not significantly higher (fold change <2, P > 0.05) than that of the S plants. This study is the first report that in grass species, the newly identified ACCase Trp-1999-Gly mutation is associated with ACCase-inhibiting herbicide resistance.
研究领域:
植物学
·
遗传学
·
农业科学
·
生物化学
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产品关联
DOI
PubMed
高影响因子
PEST MANAGEMENT SCIENCE
·
2021
·Vol. 77
·期 5
·2576-2583
·
IF 4.845
Wei Deng,Mengting Yang,Yang Li,Zhiming Xia,Yongrui Chen,Shuzhong Yuan,Qian Yang
BACKGROUND Chinese sprangletop ( Leptochloa chinensis (L.) Nees) is one of main grass weeds invading Chinese rice fields. The target-site resistance (TSR) of cyhalofop-butyl have been widely reported in L. chinensis populations, but the non-target-site resistance (NTSR) mechanisms have not yet been well-characterized. This study aims to investigate the likely NTSR in a cyhalofop-butyl-resistant L. chinensis population (YZ-R), which was collected from Yangzhou city, Jiangsu Province, China. RESULTS Dose–response assays showed the YZ-R population exhibited 191.6-fold resistance to cyhalofop-butyl, compared to the susceptible population (YZ-S). This resistance is not target-site based, because no mutations in the two ACCase genes were detected in the YZ-R plants compared to the YZ-S plants, and the ACCase genes expression levels were similar in YZ-S and YZ-R plants. In addition, the cytochrome P450 inhibitor malathion and piperonyl butoxide (PBO), and glutathione S-transferase (GST) inhibitor 4-chloro-7-nitrobenzoxadiazole (NBD-Cl) did not significantly reverse cyhalofop-butyl resistance in the YZ-R population. However, liquid chromatography−mass spectrometry (LC–MS) analysis indicated that the metabolic rates of cyhalofop acid in YZ-R plants was significantly faster (5 to 10- fold) than in YZ-S plants. Furthermore, the YZ-R population showed no cross-resistance to other ACCase-inhibiting herbicides. CONCLUSION These results indicated that cyhalofop-butyl resistance in the YZ-R population is due to non-target-site based enhanced herbicide metabolism. Resistance in this population is likely involved in a specific detoxification enzyme, with possible high catalytic efficiency and strong substrate specificity, therefore leading to high-level and single resistance to cyhalofop-butyl. © 2021 Society of Chemical Industry
研究领域:
植物学
·
农业科学
·
分子生物学
✓ 已验证
DOI
高影响因子
PEST MANAGEMENT SCIENCE
·
2024
·
IF 3.8
Minghao Jiang,Xumiao Wang,Wei Hu,Zezhou Wang,Huaiji Guan,Ning Zhao,Min Liao,Haiqun Cao
BACKGROUND Chinese sprangletop [ Leptochloa chinensis (L.) Nees] control is threatened by resistance to acetyl-CoA carboxylase (ACCase)-inhibiting herbicides. In this study, a L. chinensis population, HFLJ18, that survived cyhalofop-butyl [aryloxyphenoxypropionate (APP) herbicide, CyB] treatment was collected from a rice field in Lujiang County, Anhui Province, China. This study aimed to evaluate the susceptibility of HFLJ18 to herbicides with different modes-of-action and investigate the potential mechanisms of resistance to CyB. RESULTS The HFLJ18 population exhibited high levels of resistance to CyB (10.92-fold) and showed resistance to the ACCase inhibitors metamifop (4.63-fold) and fenoxaprop- P -ethyl (8.39-fold), but was susceptible to clethodim, pinoxaden, florpyrauxifen-benzyl, oxadiazon and pretilachlor. Target gene sequencing revealed a novel Trp-to-Gly substitution at codon position 2027 of ACCase in the resistant plants. Molecular docking revealed that the spatial structure of ACCase changed significantly following the substitution, as indicated by reduced H-bonds. A newly derived cleaved amplified polymorphic sequence (dCAPS) marker was subsequently developed to detect the Trp-2027-Gly mutation in the ACCase of L. chinensis . Additionally, pretreatment with the cytochrome P450 (P450) inhibitor piperonyl butoxide (PBO) and the glutathione S-transferase (GST) inhibitor 4-chloro-7-nitrobenzoxadiazole (NBD-Cl) did not reverse resistance to CyB, suggesting that nontarget-site resistance mechanisms were not involved in CyB resistance in the HFLJ18 population. CONCLUSION Overall, the resistance to CyB in the HFLJ18 population derived from the mutation of ACCase gene, and to the best of our knowledge, this is the first report of the ACCase Trp-2027-Gly mutation conferring resistance to ACCase-inhibiting herbicides in grass species. © 2024 Society of Chemical Industry.
研究领域:
植物科学
·
分子生物学
·
农业化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
·
2024
·
IF 4.2
Min Liao,Minghao Jiang,Xumiao Wang,Wei Hu,Ning Zhao,Haiqun Cao
Acetyl-CoA carboxylase (ACCase)-inhibiting herbicides are among the most commonly used herbicides to control grassy weeds, especially Leptochloa chinensis , in rice fields across China. Herein, we collected a suspected resistant (R) population of L. chinensis (HFLJ16) from Lujiang county in Anhui Province. Whole plant dose response tests showed that, compared with the susceptible (S) population, the R population showed high resistance to cyhalofop-butyl (22-fold) and displayed cross-resistance to metamifop (9.7-fold), fenoxaprop- P -ethyl (18.7-fold), quizalofop- P -ethyl (7.6-fold), clodinafop-propargyl (12-fold) and clethodim (8.4-fold). We detected an amino acid substitution (Cys-2088-Arg) in the ACCase of resistant L. chinensis . However, ACCase gene expression levels were not significantly different ( P > 0.05) between R plants and S plants, without or with cyhalofop-butyl treatment. Furthermore, pretreatment with piperonyl butoxide (PBO, a cytochrome P450 monooxygenase (CYP450) inhibitor) or 4-chloro-7-nitrobenzoxadiazole (NBD-Cl, a glutathione-S-transferase (GST) inhibitor), inhibited the resistance of the R population to cyhalofop-butyl significantly (by approximately 60% and 26%, respectively). Liquid chromatography tandem mass spectrometry analysis showed that R plants metabolized cyhalofop-butyl and cyhalofop acid (its metabolite) significantly faster than S plants. Three CYP450 genes, one GST gene, and two ABC transporter genes were induced by cyhalofop-butyl and were overexpressed in the R population. Overall, GST-associated detoxification, CYP450 enhancement, and target-site gene mutation are responsible for the resistance of L. chinensis to cyhalofop-butyl.
研究领域:
植物科学
·
分子生物学
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杂草科学
·
除草剂抗性
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）