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RUSSIAN JOURNAL OF GENERAL CHEMISTRY · 2025 ·Vol. 95 ·期 3 ·644-653 · IF 0.8

Design, Efficient One-Step Synthesis of Bromo-p-hydroxybenzamides and Herbicidal Activity Evaluation

Wang J.,Zhou Y.,Wu X.,Zhou X.,Sun Y.,Wu W.,Wang X.

Discovering super-efficient herbicides with novel structures is one of the effective ways to solve the increasingly severe weed resistance problem and meet ecological requirements. In this work, a series of novel bromo- p -hydroxybenzamides were designed based on the molecular hybridization strategy, and rapidly synthesized by one-step amidation reaction, and then characterized by 1 H NMR, 13 C NMR and HRMS. The herbicidal activity assay indicated that most of the target compounds exhibited good-to-excellent inhibition effects on seed germination of two model plants. At a concentration of 100 mg/L, the inhibition rate of 3,5-dibromo- N -(4-bromo-3-chlorophenyl)- p -hydroxybenzamide reached up to 98 and 96% on the roots and stalks of the monocotyledonous barnyard grass ( E. crus-galli ), respectively. 3,5-Dibromo- N -(2-bromophenyl)- p -hydroxybenzamide showed excellent inhibitory activity on the roots and stalks of dicotyledonous rape ( B. napus ) at 100 mg/L, with an inhibitory rate of more than 90%. Furthermore, the concentration was reduced to 1 mg/L, the inhibitory rate of 3,5-dibromo- N -(2-bromophenyl)- p -hydroxybenzamide on the roots of B. napus was still as high as 90%. This work provides a novel molecular scaffold for the development and research of new super-efficient herbicides.

研究领域: 农药化学 · 植物生理学
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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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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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