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fenoxaprop-P-ethyl
CROP PROTECTION · 2020 · IF 2.381

Cross resistance patterns to acetyl-CoA carboxylase inhibiting herbicides associated with different mutations in Italian ryegrass from China

Pei Zhang,Yangyang Zhang,Xiling Chen,Liyao Dong

Fenoxaprop- P -ethyl is widely used to control the Italian ryegrass ( Lolium multiflorum Lam.) in China. Recently, Italian ryegrass populations have been reported with resistance to fenoxaprop- P -ethyl in two provinces (Jiangsu and Henan) of China. It was important to clarify the resistance patterns of these populations which had evolved resistance to fenoxaprop- P -ethyl. In this study, we investigated three Italian ryegrass populations (HZGX-2, HZYC-4, and HZYC-5) that were involved with high resistance to fenoxaprop- P -ethyl. The HZGX-2 population showed low cross-resistance to clethodim, haloxyfop- R -methyl, clodinafop-propargyl, and quizalofop- P -ethyl, but was still susceptible to sethoxydim and pinoxaden. The HZYC-4 and HZYC-5 populations showed cross resistance to all tested acetyl-coenzyme A carboxylase (ACCase) inhibiting herbicides. We examined the genetic changes in three Italian ryegrass populations and identified four mutations, named D2078G, C2088R, I1781L, and I2041N and occurring within different frequencies in these populations. These mutations have been reported to underlie resistance to ACCase-inhibiting herbicides. In the HZGX-2 population wild type frequency was 73%, and the mutation frequencies at positions 1781, 2041, and 2078 were 13%, 7%, and 7%, respectively. In the HZYC-4 population, the mutation frequencies were 93% at 1781 and 7% at 2041. In the HZYC-5 population, the mutation frequencies were 72% at 1781, 16% at 2041, and 12% at 2088. There was no wild type found in the HZYC-4 and HZYC-5 populations, either. The cytochrome P450 inhibitors was shown to slightly reduce the ED 50 values of fenoxaprop-P-ethyl-resistant populations, which implied a combination of target-site resistance and non-target-site resistance was involved in resistance. This study can help the weed management of agricultural activities in China and other countries.

CAS / MDL: 51-03-6
研究领域: 植物学 · 遗传学 · 农业科学
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WEED SCIENCE · 2017 ·Vol. 65 ·期 6 ·710-717 · IF 1.862

Mechanism of Fenoxaprop-P-ethyl Resistance in Italian Ryegrass (Lolium perenne ssp. multiflorum) from China

Pei Zhang,Han Wu,Hongle Xu,Yuan Gao,Wei Zhang,Liyao Dong

Italian ryegrass has invaded wheat fields in China and is becoming a predominant, troublesome weed. Fenoxaprop-P-ethyl has been widely used for weed control on Chinese farms since the 1990s. However, overuse has led to fenoxaprop-P-ethyl resistance in Italian ryegrass in Chinese wheat fields. In this study, we identified a putative fenoxaprop-P-ethyl–resistant population of Italian ryegrass, HZYC-6, from Henan province, China. Mutations involving Asp-2078-Gly and Ile-1781-Leu substitutions were identified in the carboxyl-transferase domain of acetyl-coenzyme A carboxylase in this population, and these mutations are the likely cause of the target site–based resistance to fenoxaprop-P-ethyl. In addition, we identified cytochrome P450–mediated metabolism of herbicides (non–target site based resistance) in the HZYC-6 population, indicating that multiple mechanisms of resistance may be segregating in this population. Furthermore, HZYC-6 was also highly resistant to haloxyfop-R-methyl and quizalofop-P-ethyl, moderately resistant to clodinafop-propargyl and sethoxydim, and had low resistance to clethodim and pinoxaden.

研究领域: 杂草科学 · 植物生理学 · 分子生物学
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Plants-Basel · 2024 ·Vol. 13 ·期 20 ·2946 · IF 4

The Mitigating Effects of Perilla Leaf Essential Oil on the Phytotoxicity of Fenoxaprop-P-Ethyl in Rice Seedlings

Jiuying Li,Yinghui Zhu,Lanlan Sun,Hongle Xu,Wangcang Su,Fei Xue,Chuantao Lu,Wenwei Tang,Renhai Wu

Fenoxaprop-P-ethyl (FE) can effectively control weeds in rice fields, but it has been found to cause phytotoxicity in rice. In this study, the phytotoxicity of FE was mitigated by perilla leaf essential oil (PEO) in rice seedlings. The injury recovery rates (IRRs) for shoot length and fresh weight treated with 800 mg/L of PEO were 101.51% and 99.05%, respectively. Moreover, the damage ofs-metolachlor and pretilachlor was also alleviated when co-applied with 800 mg/L PEO; the IRR ofs-metolachlor phytotoxicity was 26.07% and 27.34%, respectively, and the IRR of pretilachlor phytotoxicity was 127.27% and 124.39%, respectively. However, PEO had no significant effect on the phytotoxicity of pinoxaden, mesotrione, penoxsulam, mesosulfuron-methyl, and nicosulfuron. The results of GC–MS analysis showed that a total of 23 components were detected in PEO, among which linalool (36.49%), linalyl formate (26.96%), α-terpineol (10.63%), 2-hexanoylfuran (5.81%), geranyl acetate (4.13%), and neryl acetate (2.30%) were the primary components. Among them, 2-hexanoylfuran was the most effective component to alleviate FE damage, for which the IRR of shoot length and fresh weight was 73.17% and 73.02%, respectively, followed by the geranyl acetate, for which the IRR was 72.32% and 60.56%, respectively, and neryl acetate, for which the IRR was 65.28% and 58.11%, respectively. Furthermore, the application of 50 mg/L of 2-hexanofuran significantly improved the tolerance of shoot length and fresh weight to FE stress by factors of 5.32 and 5.35, respectively. This research demonstrates that PEO and 2-hexanoylfuran have the potential to serve as natural safeners to reduce phytotoxicity.

CAS / MDL: 105-87-3
研究领域: 农业科学 · 植物生理学 · 植物化学
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PEST MANAGEMENT SCIENCE · 2018 ·Vol. 75 ·期 1 ·204-214 · IF 3.249

Target site mutations and cytochrome P450s confer resistance to fenoxaprop-P-ethyl and mesosulfuron-methyl in Alopecurus aequalis

Ning Zhao,Yanyan Yan,Lu'an Ge,Baolin Zhu,Weitang Liu,Jinxin Wang

BACKGROUND Shortawn foxtail ( Alopecurus aequalis Sobol.) is a competitive grass weed infesting winter wheat- and canola-growing fields in China. In May 2016, a suspected A. aequalis resistant population AHTC-06 that survived fenoxaprop- P -ethyl and mesosulfuron-methyl applied at their field-recommended rates was collected from a wheat field in Jinji County, Anhui Province, China. This study aimed to determine the resistance profile of this AHTC-06 population to ACCase- and ALS-inhibitors, and to investigate its mechanisms of resistance to fenoxaprop- P -ethyl and mesosulfuron-methyl. RESULTS Two mutations, a common Ile-2041-Asn ( ACCase gene) and a very rare Pro-197-Tyr ( ALS1 gene), were both identified in resistant individual plants. The homozygous subpopulation AHTC-06F1 for the two mutations was generated, and it showed broad-spectrum resistance to APPs, DENs, and ALS-inhibiting herbicides of all five chemical families tested, with resistance index (RI) values that ranged from 2.2 to 36.5. In vitro ALS activity assays showed the ALS from the resistant population was insensitive to all the tested ALS inhibitors, with RI values ranging from 3.10 to 22.51. Pre-treatment with piperonyl butoxide (PBO) and malathion significantly ( P < 0.05) reversed the weed's resistance to fenoxaprop- P -ethyl and mesosulfuron-methyl, respectively. Two P450 genes, c21190_g1 and c43350_g3 , were constitutively overexpressed and mesosulfuron-methyl-induced upregulated in resistant plants, for which c43350_g3 was also fenoxaprop- P -ethyl-induced upregulated. CONCLUSION This study confirms the first case of a grass weed featuring broad-spectrum resistance to ALS-inhibiting herbicides due to a Pro-197-Tyr mutation in the ALS gene. Fenoxaprop- P -ethyl and mesosulfuron-methyl resistances in AHTC-06 plants were conferred by target site mutations and P450s-based metabolism. © 2018 Society of Chemical Industry

CAS / MDL: 51-03-6
研究领域: 植物科学 · 杂草科学 · 分子生物学 · 遗传学
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JOURNAL OF MOLECULAR LIQUIDS · 2024 · IF 5.3

Solubility measurement, calculation, solvent effect and preferential solvation of fenoxaprop-p-ethyl in four cosolvent mixtures at (278.15–323.15) K

Renjie Xu,Ganbing Yao

Equilibrium solubility of fenoxaprop-p-ethyl in aqueous mixtures of ethanol/ isopropanol/acetonitrile/ N,N -dimethylformamide (DMF) plus water was experimentally measured by isothermal saturation method at (278.15–323.15) K under 101.2 kPa. The order of solubility (mole fraction) of fenoxaprop-p-ethyl in pure solvents from high to low is 4.233 × 10 −2 (DMF 323.15 K) > 2.044 × 10 −2 (acetonitrile 323.15 K) > 7.727 × 10 −3 (isopropanol 323.15 K) > 5.338 × 10 −3 (ethanol 323.15 K) > 2.565 × 10 −5 (water 323.15 K). Experimental results showed that temperature and type of solvent were decisive factors for the dissolution of fenoxaprop-p-ethyl. The content of fenoxaprop-p-ethyl in solution was analyzed by high-performance liquid chromatography (HPLC). Moreover, the solubility data of fenoxaprop-p-ethyl was correlated by Jouyban-Acree (J-A) model, van’t Hoff-Jouyban-Acree (V-J-A) model and Apelblat-Jouyban-Acree (A-J-A) model. The maximum of root-mean-square deviation ( RMSD ), relative average deviation ( RAD ) and standard deviation ( SD ) predicted via three thermodynamic models were 1.78 × 10 −4 (DMF + water), 2.87 × 10 −2 (acetonitrile + water) and 1.79 × 10 −4 (DMF + water), respectively. In addition, the solvent effect between solute and solvent molecules was deduced by KAT-LSER model and the result showed that dipolarity/polarizability interactions between the solute and solvent molecules were dominant in the dissolution of fenoxaprop-p-ethyl. Finally, the preferential solvation parameter ( δx 1,3 ) of fenoxaprop-p-ethyl was obtained by the method of inverse Kirkwood–Buff integrals and the preferential dissolution behavior of each concentration range is explained by Lewis acid base theory. However, for acetonitrile  + water, the change of δx 1,3 may be due to the polarization effects and it is not suitable for Lewis acid base theory.

CAS / MDL: 71283-80-2 67-63-0
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PEST MANAGEMENT SCIENCE · 2019 ·Vol. 75 ·期 12 ·3175-3183 · IF 3.255

Trp-1999-Ser mutation of acetyl-CoA carboxylase and cytochrome P450s-involved metabolism confer resistance to fenoxaprop-P-ethyl in Polypogon fugax

Ning Zhao,Lu'an Ge,Yanyan Yan,Shuang Bai,Dandan Wang,Weitang Liu,Jinxin Wang

BACKGROUND Asia minor bluegrass ( Polypogon fugax Nees ex Steud.) is an invasive grass species severely infesting wheat and canola fields in China. In May 2017, a suspected resistant P. fugax population AHHY that survived fenoxaprop- P -ethyl applied at its field-recommended rate was collected from a wheat field in Huaiyuan County, Anhui Province, China. This study aimed to determine the resistance profile of AHHY to acetyl-CoA carboxylase (ACCase) inhibitors and to investigate its mechanisms of resistance to fenoxaprop. RESULTS Single-dose testing indicated that the AHHY population had evolved resistance to fenoxaprop. The partial carboxyltransferase domain of ACCase in P. fugax was amplified and compared. Four loci encoding plastidic ACCase were isolated from both the resistant and sensitive individuals. Combining gene sequencing with the derived cleaved amplified polymorphic sequence assay, we found that 100% of the plants of AHHY carried Trp-1999-Ser mutation in their ACCase1,1–2 allele. Whole-plant dose–response bioassay indicated that AHHY was highly resistant to fenoxaprop and pinoxaden (resistance index (RI) ≥ 10) with low resistance to clodinafop-propargyl, sethoxydim, and clethodim (2 ≤ RI < 5). Pre-treatment with piperonyl butoxide largely reduced (55%) the weed's resistance to fenoxaprop. Both basal and fenoxaprop-induced glutathione S -transferases activities toward 1-chloro-2, 4-dinitrobenzene were significantly higher in resistant plants than in susceptible plants. CONCLUSION This study revealed that P. fugax had multiple alleles encoding plastidic ACCase, and reported for the first time the occurrence of Trp-1999-Ser mutation and non-target-site resistance in this species. Fenoxaprop resistance in AHHY plants was conferred by target-site mutation and P450s-involved enhanced metabolism. © 2019 Society of Chemical Industry

CAS / MDL: 51-03-6
研究领域: 植物学 · 植物生理学 · 分子生物学 · 杂草科学
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2013 · IF 2.111

The role of cytochrome P450 monooxygenase in the different responses to fenoxaprop-P-ethyl in annual bluegrass (Poa annua L.) and short awned foxtail (Alopecurus aequalis Sobol.)

Wang Hongchun,Li Jun,Lv Bo,Lou Yuanlai,Dong Liyao

Herbicide resistance or tolerance in weeds mediated by cytochrome P450 monooxygenase is a considerable problem. However, cytochrome P450 mediated resistance or tolerance in weeds was less studied. Thus, in this work, the role of the cytochrome P450 monooxygenase in the different responses of Poa annua and Alopecurus aequalis to fenoxaprop-P-ethyl was studied. We found that the effect of fenoxaprop-P-ethyl could be synergized by piperonyl butoxide (PBO) in P. annua , but not by malathion. After being treated with fenoxaprop-P-ethyl (containing mefenpyr-diethyl), the contents of cytochrome P450 and cytochrome b 5 in P. annua increased significantly compared to plants treated with mefenpyr-diethyl only or untreated plants. However, the increase was less in A. aequalis , which was susceptible to fenoxaprop-P-ethyl. The activities of ρ-nitroanisole O-demethylase (PNOD), ethoxyresorufin O-deethylase (EROD), ethoxycoumarin oxidase (ECOD) and NADPH-dependent cytochrome P450 reductase mediated by cytochrome P450 monooxygenase increased in P. annua after treatment with fenoxaprop-P-ethyl, especially the activities of ECOD and cytochrome P450 reductase. Besides this, cytochrome P450 monooxygenase activity toward fenoxaprop-P-ethyl in P. annua increased significantly compared to untreated or treated with mefenpyr-diethyl plants and treated or untreated A. aequalis . Cytochrome P450 monooxygenase may play an important role in the different responses to fenoxaprop-P-ethyl in P. annua and A. aequalis .

CAS / MDL: 51-03-6
研究领域: 植物学 · 农学 · 分子生物学
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