Study on the selectivity and phloem mobility of Fenoxaprop-P amino acid ester conjugates on rice and barnyard grass

• Published in: Pesticide biochemistry and physiology 2022-05, Vol.183, p.105086-105086, Article 105086
• Main Authors: Lu, Xingliang, Qin, Chuan, Cai, Jinlong, Zhang, Min, Yu, Linhua, Li, Junkai, Wu, Qinglai
• Format: Article
• Language: English
• Subjects: Amino acid ester conjugates; Amino Acids - metabolism; Aryloxyphenoxypropionate(APP); Echinochloa - metabolism; Esters - metabolism; Herbicides - chemistry; Herbicides - toxicity; Oryza - metabolism; Phloem - physiology; Phloem mobility; Selectivity
• ISSN: 0048-3575; 1095-9939
• DOI: 10.1016/j.pestbp.2022.105086

To improve the selectivity of the fenoxaprop herbicide to rice and barnyard grass, a series of fenoxaprop-P-ethyl-amino acid ester conjugates were designed and synthesized, and tested for biological activity as well as their phloem mobility. The bioassay results indicated that the target compounds possessed better activity against barnyard grass (Echinochloa crusgalli) than rape (Brassica campestris L.) at the concentration of 0.5 mmol/L. Compounds 3h and 3i, showed more than 70% control efficiency against barnyard grass, while less than 30% for rape. The compounds showed less impact on rice after spray treatment than in the germination test. Compounds 3i, 3j, and 3k showed excellently herbicidal activities against barnyard grass and low phytotoxicity to rice. Compound 3k showed 6.1% phytotoxicity to rice at a spray concentration of 0.25 mmol/L, better than fenoxaprop-P-ethyl (61.6%) at the same concentration. The selectivity results of the target compounds revealed that most of compounds obviously reduced phytotoxicity to rice while retaining herbicidal activity of barnyard grass. The herbicidal activity of compound 3d compared to FPE was increased by 50%, while its safety on rice was also increased by 50%. The concentration of the compounds in barnyard grass roots was higher than in rice roots, showing greater phloem mobility. In particular, the concentration of compound 3d on barnyard grass exhibited 142.72 mg/kg which was 3 times as much as Fenoxaprop, while its concentration on rice exhibited 3.65 mg/kg, the results revealed that the difference of phloem mobility might be the important reason for causing the selectivity. [Display omitted] •Introduction of amino acid ester to Fenoxaprop-P-ethyl leading to the phloem mobility.•Different phloem mobility of Fenoxaprop-P-ethyl conjugates results in the selectivity on Rice and Barnyard grass.•Anti-Kleier model compounds can also have a good phloem mobility.•Safety of Fenoxaprop-P alanine ester conjugates on rice has improved compared with Fenoxaprop-P-ethyl.