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WEED SCIENCE · 2025 · IF 2.5

A Cys-2088-Arg mutation in ACCase confers cross-resistance to ACCase-inhibiting herbicides in barnyard grass (Echinochloa crus-galli)

Wei Hu,Yuguo Li,Chaowei Zhao,Liya Zhang,Yumeng Ma,Quan Gao,Haiqun Cao,Min Liao

Barnyardgrass [Echinochloa crus-galli (L.) P. Beauv.] is a dominant weed species occurring in rice fields across China. Metamifop, a common herbicide, is frequently applied to control E. crus-galli and other grassy weeds in rice fields. Herein, HS01, an E. crus-galli population suspected to be resistant (R) to metamifop, was collected from Hanshan County in Anhui Province. Whole-plant dose-response testing revealed that, compared with the susceptible (S) population FD03, HS01 had developed high-level resistance to metamifop with a resistance index (RI) of 11.76 and showed cross-resistance to cyhalofop-butyl (RI=9.33), fenoxaprop-P-ethyl (RI=5.80) and clethodim (RI=3.24). Gene sequencing revealed a Cys-2088-Arg mutation in ACCase 1,5 allele of all the R plants, while ACCase gene overexpression was not involved in the resistance. Molecular docking indicated that the less negative binding energies might be the main reason for the resistance of HS01 to ACCase-inhibiting herbicides. A derived cleaved amplified polymorphic sequence (dCAPS) method was developed for the rapid identification of the Cys-to-Arg mutation in the ACCase gene at codon position 2088 in E. crus-galli. Additionally, pretreatment with the cytochrome P450 inhibitor piperonyl butoxide or the glutathione S-transferase inhibitor 4-chloro-7-nitrobenzoxa-diazole had no significant effects (p> 0.05) on the resistance of HS01 to metamifop. To our knowledge, this is the first report of a Cys-2088-Arg mutation in E. crus-galli ACCase that confers cross-resistance to ACCase-inhibiting herbicides.

CAS / MDL: 10199-89-0 51-03-6
研究领域: 植物学 · 分子生物学 · 农业科学
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JOURNAL OF PLANT GROWTH REGULATION · 2017 ·Vol. 37 ·期 3 ·745-754 · IF 2.073

Increasing Rice Allelopathy by Induction of Barnyard Grass (Echinochloa crus-galli) Root Exudates

Zhang Qi,Li Li,Li Jiayu,Wang Haibin,Fang Changxun,Yang Xiaoyan,He Haibin

An allelopathic rice PI312777 and a non-allelopathic rice Lemont were hydroponically cultured and treated with extracts of seeds and tissues and root exudates of barnyard grass ( Echinochloa crus-galli , BYG) to induce an allelopathic response. The results of bioassays showed that the % inhibition of two rice leaf extracts was significantly ( p  < 0.05) increased by treatment with BYG root exudates. This induced trait was dosage- and time-dependent. The highest % inhibition for both PI312777 and Lemont was obtained following treatment with 15 mL of BYG root exudates for 2 days. Under these conditions, total allelopathy (TA) values of PI312777 on root length, plant height, and plant dry weight of BYG were 73.39, 68.01, and 70.42%, respectively, and induced allelopathy (IA) values were 21.53, 17.04, and 16.62%, respectively, accounting for 24–29% of TA. Correspondingly, TA values of Lemont were 28.38, 21.38, and 23.38%, respectively, and IA values were 14.49, 11.37, and 12.11%, respectively, accounting for 51–53% of TA. The % inhibition of two rice culture solutions was in agreement with the results of their leaf extracts. The total contents of 7 phenolic acids in the culture solutions of PI312777 and Lemont were 2.18 and 1.47 times, respectively, as much as those in the control solutions. The phenylalanine ammonia-lyase ( PAL ) gene in PI312777 leaves was significantly up-regulated after induction treatments. The results indicated that rice allelopathy is a chemical induction mechanism, and confirmed that chemical induction to raise rice allelopathy is a practical and feasible method.

研究领域: 植物学 · 农业科学 · 分子生物学
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Agronomy-Basel · 2022 ·Vol. 12 ·期 11 ·2724 · IF 3.949

Metabolic Resistance to Acetyl-CoA Carboxylase-Inhibiting Herbicide Cyhalofop-Butyl in a Chinese Echinochloa crus-galli Population

Qian Yang,Xia Yang,Jinlei Zhu,Tian Wei,Min Lv,Yongfeng Li

A population ofEchinochloa crus-galli(L.) P. Beauv obtained from direct-seeding rice fields in Jiangxi Province, China, exhibited high resistance levels (13.5-fold) to the acetyl-CoA carboxylase (ACCase)-inhibiting herbicide cyhalofop-butyl. Compared with the susceptible (S) population, this resistant (R) population evolved a cross-resistance to aryloxyphenoxypropionates (APPs) herbicides metamifop (2.9-fold) and fenoxapro-p-ethyl (4.1-fold), cyclohexanediones (CHDs) herbicide clethodim (4.7-fold), phenyl pyrazoline (DEN) herbicide pinoxaden (6.4-fold), and evolved multiple-resistance to acetolactate synthase (ALS)-inhibiting herbicide penoxsulam (3.6-fold), and auxin mimic herbicides quinclorac (>34.7-fold) and florpyrauxifen-benzyl (2.4-fold).ACCasegene sequencing did not reveal the existence of any known mutation point conferring with herbicide resistance. In addition, three metabolic inhibitors—one glutathione—S-transferase (GST) inhibitor (NBD-Cl), and two cytochrome P450 inhibitors (malathion and PBO)—did not reverse the cyhalofop-butyl resistance. Furthermore, enhanced metabolic rates of more than 60% 24 h after treatment with the active compound cyhalofop acid was observed in R plants compared to S plants. Hence, enhanced metabolism activity endows a non-target-site resistance to cyhalofop-butyl in the R population ofE. crus-galli. Future research will be required to determine what metabolizing enzyme genes are responsible for cyhalofop-butyl resistance inE. crus-galli.Keywords:resistance mechanisms;metabolism;cyhalofop-butyl;Echinochloa crus-galli;resistance pattern;multiple-resistance

CAS / MDL: 10199-89-0 51-03-6
研究领域: 植物学 · 遗传学 · 农学
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WEED SCIENCE · 2024 · IF 2.1

A Trp-574-Leu mutation in acetolactate synthase confers imazamox resistance in barnyardgrass (Echinochloa crus-galli) from China

Yu Liu,Kerong Shi,Haitao Gao,Shaojing Yin,Liyao Dong,Zhike Feng

Barnyardgrass [Echinochloa crus-galli (L.) P. Beauv.] is increasingly infesting imidazolinone-tolerant (IMI-T) rice fields in China, imazamox resistance of E. crus-galli has become the major concern for weed management in IMI-T rice fields. In this study, the susceptible population JLGY-3 (S) and the suspected resistant population JHXY-2 (R) collected from IMI-T rice fields were used as research subjects. When treated with imazamox, JHXY-2 (R) population showed a high level of herbicide resistance with a resistance index (RI) of 31.2. JHXY-2 (R) was cross-resistant to all five acetolactate synthase (ALS) inhibitors from different chemical families, but sensitive to herbicides inhibiting acetyl-CoA carboxylase (ACCase). In order to understand the reason why JHXY-2 (R) was resistant to imazamox, we performed experiments to characterize potential TSR and NTSR mechanisms. A trp-574-leu amino acid mutation in ALS and low imazamox ALS sensitivity were the main mechanism underlying imazamox resistance in this JHXY-2 (R) population. There was no significant difference in ALS gene expression and ALS protein abundance between R and S populations. High-performance liquid chromatography-tandem mass spectrometry analysis showed enhanced metabolism of imazamox in JHXY-2 (R), which was in contrast to the results of pretreatment with a metabolic enzyme inhibitor. Treatments with the P450/GST inhibitors did not alter the resistance level of JHXY-2 (R) against imazamox. To further clarify the NTSR mechanism of JHXY-2 (R), transcriptome sequencing showed that there was almost no significant difference in the expression of P450 and GST metabolic enzyme genes between R and S populations, and only GST-U1 showed a significant induction in R population. In conclusion, amino acid mutation and higher enzyme activity of ALS are the main causes of imazamox resistance in JHXY-2 (R). However, given the differences in imazamox residues in the leaves of the E. crus-galli, there may still be undetectable NTSR that are causing imazamox resistance in the R population.

CAS / MDL: 513-86-0
研究领域: 植物学 · 遗传学 · 农业科学
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PEST MANAGEMENT SCIENCE · 2024 · IF 3.8

A novel mutation Trp-2027-Gly in acetyl-CoA carboxylase confers resistance to cyhalofop-butyl in Chinese sprangletop (Leptochloa chinensis)

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.

CAS / MDL: 10199-89-0 51-03-6
研究领域: 植物科学 · 分子生物学 · 农业化学
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PEST MANAGEMENT SCIENCE · 2023 ·Vol. 79 ·期 8 ·2725-2736 · IF 4.1

Metamifop resistance in Echinochloa glabrescens via glutathione S-transferases-involved enhanced metabolism

Qi Li,Ning Zhao,Minghao Jiang,Mali Wang,Jingxu Zhang,Haiqun Cao,Min Liao

BACKGROUND Echinochloa glabrescens Munro ex Hook. f. is one of the main Echinochloa spp. seriously invading Chinese rice fields and has evolved resistance to commonly used herbicides. Previously, an E. glabrescens population (LJ-02) with suspected resistance to the acetyl-CoA carboxylase (ACCase)-inhibiting herbicide metamifop was collected. This study aimed to determine its resistance status to metamifop and investigate the internal molecular mechanisms of resistance. RESULTS Single-dose testing confirmed that the LJ-02 population had evolved resistance to metamifop. Gene sequencing and a relative expression assay of ACCase ruled out target-site based resistance to metamifop in LJ-02. Whole-plant bioassays revealed that, compared with the susceptible population XZ-01, LJ-02 was highly resistant to metamifop and exhibited cross-resistance to fenoxaprop- P -ethyl. Pretreatment with the known glutathione S -transferase (GST) inhibitor, 4-chloro-7-nitrobenzoxadiazole (NBD-Cl), largely reversed the resistance to metamifop by approximately 81%. Liquid chromatography–tandem mass spectrometry analysis indicated that the metabolic rates of one of the major metabolites of metamifop, N -(2-fluorophenyl)-2-hydroxy- N -methylpropionamide (HPFMA), were up to 383-fold faster in LJ-02 plants than in XZ-01 plants. There were higher basal and metamifop-inducible GST activities toward 1-chloro-2,4-dinitrobenzene (CDNB) in LJ-02 than in XZ-01. Six GST genes were metamifop-induced and overexpressed in the resistant LJ-02 population. CONCLUSION This study reports, for the first time, the occurrence of metabolic metamifop resistance in E. glabrescens worldwide. The high-level metamifop resistance in the LJ-02 population may mainly involve specific isoforms of GSTs that endow high catalytic activity and strong substrate specificity. © 2023 Society of Chemical Industry.

CAS / MDL: 930-55-2 51-03-6
研究领域: 植物科学 · 分子生物学 · 杂草科学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2023 · IF 6.1

Ile-1781-Leu Target Mutation and Non-Target-Site Mechanism Confer Resistance to Acetyl-CoA Carboxylase-Inhibiting Herbicides in Digitaria ciliaris var. chrysoblephara

Qian Yang,Jinlei Zhu,Xia Yang,Tian Wei,Min Lv,Yongfeng Li

Digitaria ciliaris var. chrysoblephara is a xerophytic weed severely invading rice fields along with the application of rice mechanical direct seeding technology in China. This study identified one resistant population (M5) with an Ile-1781-Leu substitution in ACCase1 showing broad-spectrum resistance to three chemical classes of ACCase-inhibiting herbicides, including metamifop, cyhalofop-butyl, fenoxaprop-p-ethyl, haloxyfop-p-methyl, clethodim, sethoxydim, and pinoxaden. The other two populations, M2 and M4, without any resistance-responsible mutations, only exhibited resistance to aryloxyphenoxypropionate (APP) herbicides cyhalofop-butyl and fenoxaprop-p-ethyl. Pre-treatment with the cytochrome P450 monooxygenase (P450) inhibitor PBO significantly reduced the cyhalofop-butyl resistance by 43% in the M2 population. Pre-emergence weed control with soil-applied herbicides, such as pretilachlor, pendimethalin, and oxadiazon, can effectively inhibit the germination and growth of D. ciliaris var. chrysoblephara. The present study reported a xerophytic weed species invading rice fields featuring broad-spectrum resistance to ACCase-inhibiting herbicides as a result of Ile-1781-Leu mutation of ACCase. Both target- and P450-involved non-target-site mechanisms may be contributing to resistance in D. ciliaris var. chrysoblephara species.

CAS / MDL: 10199-89-0 51-03-6
研究领域: 植物学 · 遗传学 · 农学
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2025 · IF 4

Expression of Echinochloa oryzoides CYP71A1 and GSTU23 catalyzes the metabolism of thiobencarb, thereby conferring resistance

Jinhui Li,Yi Zhang,Longlong Li,Shouhui Wei,Zhaofeng Huang,Lu Chen,Hongjuan Huang

Echinochloa oryzoides (Ard.) Fritsch. is a notorious and prevalent weed in paddy fields. Thiobencarb (TB), a thiocarbamate herbicide, is widely applied in paddy fields for the control of pre-emergence weeds. However, owing to the prolonged and large-scale usage of TB, certain Echinochloa oryzoides populations have evolved resistance to it. In this study, a population of Echinochloa oryzoides from a paddy field was suspected of being resistant to the TB herbicide. Notably, this population also displayed multiple resistance and cross-resistance to Acetolactate synthase (ALS), Acetyl-CoA carboxylase (ACCase), and hormone-based herbicides. The resistance to TB was partially reversed by 50.8 % and 44.7 % upon treatment with a glutathione S-transferase (GST) inhibitor (NBD-Cl) and a cytochrome P450 inhibitor (malathion), respectively. This confirmed that metabolic resistance was the predominant mechanism underlying the observed resistance. RNA-seq analysis uncovered the overexpression of CYP71A1 and GSTU23 in the resistant (R) population. This study is the first to screen and validate metabolic enzymes capable of effectively metabolizing TB in an Echinochloa oryzoides . Functional verification was conducted using a yeast in vitro expression system, which confirmed the metabolic capabilities of both CYP71A1 and GSTU23 genes towards TB. Collectively, these findings demonstrate that the overexpression of CYP71A1 and GSTU23 in the R population endows Echinochloa oryzoides with the evolutionary capacity to develop resistance to thiobencarb. This study has shed light on the resistance mechanisms of Echinochloa oryzoides to TB, thereby enhancing our understanding of its herbicide tolerance. Moreover, these results highlight the necessity for targeted strategies to control resistant populations, ultimately contributing to more effective and sustainable herbicide resistance management in agriculture.

CAS / MDL: 10199-89-0
研究领域: 植物学 · 遗传学 · 生物化学 · 农业科学
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LANGMUIR · 2022 · IF 4.331

β-Cyclodextrin/Azobenzene Microspheres Loaded with Paraquat Are Safe and Effective

Chaonan Li,Ya Wang,Zihao Wang,Xiaogang Li

Although paraquat is a widely used herbicide, it is toxic to humans if ingested or absorbed through an open wound. To improve the safety of paraquat, a new formulation of paraquat based on photoresponsive polymers was exploited. Photoresponsive β-cyclodextrin polymer microspheres (AZO-CD) were synthesized via a host–guest interaction between β-cyclodextrin and azobenzene. AZO-CD were characterized by Fourier transform infrared spectrometry, circular dichroism, ultraviolet (UV) spectrophotometry, and thermogravimetric analysis, and their photoresponsiveness was also evaluated. AZO-CD were used to load paraquat, which yielded photoresponsive paraquat-loaded microspheres. For the paraquat-loaded microspheres, irradiation with UV light or sunlight induced the isomerization of azobenzene into the cis form. Then, the cis-azobenzene was liberated from the cavities of the β-cyclodextrin. The paraquat-loaded microspheres released paraquat continuously over time. Furthermore, under UV light, the herbicidal capacity of the paraquat-loaded microspheres against barnyard grass was comparable to that of free paraquat at the same dose. Our findings show that loading paraquat into AZO-CD provides a safe and environmentally friendly herbicide formulation.

CAS / MDL: 60-09-3 108-30-5
研究领域: 农业化学 · 环境科学 · 材料科学
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2019 · IF 2.87

Transcriptome profiling to identify cytochrome P450 genes involved in penoxsulam resistance in Echinochloa glabrescens

Bojun Yan,Yuhua Zhang,Jun Li,Jiapeng Fang,Tingting Liu,Liyao Dong

Cytochrome P450s (P450s) confer resistance against herbicides, and this is increasingly becoming a concern for weed control. As a widespread Gramineae weed in paddy fields , Echinocloa glabrescens has become resistant to the acetolactate synthase (ALS)-inhibiting triazolopyrimidine herbicide penoxsulam. In this study, we found that the GR 50 of the resistant population (SHQP-R) decreased substantially from 25.6 to 5.0 and 6.2 g a.i. ha −1 after treatment with the P450 inhibitors piperonyl butoxide (PBO) and malathion , respectively. However, P450 inhibitors almost had no effects on the susceptibility of the sensitive population (JYJD-S) to penoxsulam. To investigate the mechanisms of metabolic resistance, transcriptome sequencing analysis was performed to find candidate genes that may confer resistance to penoxsulam in E. glabrescens . A total of 233 P450 differentially expressed genes (DEGs) were identified by transcriptome sequencing. We found that the metabolic process and metabolic pathways were the most highly enriched in DEGs. Further, twenty-seven candidate P450 DEGs were selected for qPCR validation analyses. After penoxsulam treatment, the relative expression levels were significantly higher in SHQP-R than in JYJD-S. Among these, the relative expression of twenty-three P450 DEGs (eighteen from the CYP72A-71C-74A-96A-734A subfamily; five from CYP81E1-94C1–94B3-714C1-714C2) were upregulated and four P450 DEGs (from CYP724B1-711A1-707A7-97B2) were downregulated. Changes in the expression of these candidate P450 genes in E. glabrescens were in response to penoxsulam, which provides preliminary evidence for the role of P450s in herbicide metabolism in E. glabrescens. However, further functional studies on metabolic resistance to penoxsulam in a resistant E. glabrescens population are required.

CAS / MDL: 1317-36-8
研究领域: 植物科学 · 分子生物学 · 杂草科学 · 药理学
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2022 · IF 4.966

Mefenacet resistance in multiple herbicide-resistant Echinochloa crus-galli L. populations

Xinyi Cai,Jinyi Chen,Xiaofei Wang,Haitao Gao,Binghan Xiang,Liyao Dong

Echinochloa crus-galli L . , a notorious weed in rice paddy fields , is usually kept under control by mefenacet application at the pre-emergence or early post-emergence stage. Due to continuous and repeated usage, E. crus-galli is developing resistance to mefenacet in China. Two putative resistant and one susceptible E. crus-galli populations were collected from paddy fields in Jiangsu Province to characterize their herbicide resistance . Compared with the susceptible population , the two mefenacet-resistant populations had 2.8- and 4.1-times greater pre-emergence resistance, and 10- and 6.8-times greater early post-emergence resistance to mefenacet. These mefenacet-resistant E. crus-galli populations also exhibited cross- or multiple-resistance to acetochlor , pyraclonil, imazamox, and quinclorac. However, when the glutathione S-transferase (GST) inhibitor 4-chloro-7-nitrobenzoxadiazole (NBD-Cl) was applied prior to post-emergence treatment, mefenacet resistance levels were reduced in both populations. Additionally, GST activity in vivo in one resistant population was much higher than the susceptible population after mefenacet application. The very long chain fatty acid elongases (VLCFAEs) from both mefenacet-resistant populations required much higher mefenacet concentration to inhibit their activity. The reduced sensitivity of VLCFAEs to mefenacet indicates the presence of a target-site resistance mechanism and induction of high GST activity may provide additional contribution to E. crus-galli mefenacet resistance through a non-target-site mechanism.

CAS / MDL: 10199-89-0
研究领域: 农业科学 · 植物科学 · 杂草科学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2022 · IF 5.895

Efficient Total Synthesis and Herbicidal Activity of 3-Acyltetramic Acids: Endogenous Abscisic Acid Synthesis Regulators

Xiankun Liu,Shiqiang Wen,Weichen You,Xiaofei Wang,Qing X. Li,Qiang Bian,Pei Lv,Rimao Hua

An efficient synthesis method will allow a large number of tetramic acid analogues to be synthesized for property and potency optimization. In this study, a facile and efficient method was described for the synthesis of 3-acyltetramic acids. The synthesis was accomplished mainly via (1) mild intramolecular cyclization and (2) the formation of β-ketoamides between nucleophiles and acyl Meldrum’s acids. 3-Acyltetramic acid exhibited phytotoxicity against Echinochloa crusgalli and Portulaca oleracea. At a dosage of 750 g ha–1, 6k and 6a showed high herbicidal activity against E. crusgalli, Digitaria sanguinalis and P. oleracea, Amaranthus retroflexus, respectively. 6k inhibited the synthesis of endogenous abscisic acid, thus seedling germination and plant growth. The incorporation of various acyl Meldrum’s acids and amino acid esters was applicable to the parallel synthesis of 3-acyltetramic acids. The mode of action and herbicidal activity indicate that 3-tetramic acid had good herbicidal performance and was a promising herbicide candidate. This study will provide a reference for novel herbicide development.

研究领域: 化学 · 农业科学 · 植物生理学
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