Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 68, Issue 12, Pages 3729-3741Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.0c00947
Keywords
PPO; diphenyl ether; substructure splicing; bioisomerization; herbicidal activity; SAR; cumulative analysis
Funding
- National Natural Science Foundation of China [31572042]
- Natural Science Foundation of Heilongjiang Province of China [ZD2017002]
- Heilongjiang Province Postdoctoral Research Startup Fund [LBH-Q19083]
- Research Science Foundation in Technology Innovation of Harbin [2017RAQXJ017]
- Academic Backbone Project of Northeast Agricultural University [16XG24]
- Northeast Agricultural University SIPT College Students Innovation Practice Training Program [201910224361]
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To seek new protoporphyrinogen oxidase (PPO) inhibitors with better biological activity, a series of novel diphenyl ether derivatives containing tetrahydrophthalimide were designed based on the principle of substructure splicing and bioisomerization. PPO inhibition experiments exhibited that 6c is the most potential compound, with the half-maximal inhibitory concentration (IC50) value of 0.00667 mg/L, showing 7 times higher activity than Oxyfluorfen (IC50 = 0.0426 mg/L) against maize PPO and similar herbicidal activities to Oxyfluorfen in weeding experiments in greenhouses and field weeding experiments. In view of the inspected bioactivities, the structure-activity relationship (SAR) of this series of compounds was also discussed. Crop selection experiments demonstrate that compound 6c is safe for soybeans, maize, rice, peanuts, and cotton at a dose of 300 g ai/ha. Accumulation analysis experiments showed that the accumulation of 6c in some crops (soybeans, peanuts, and cotton) was significantly lower than Oxyfluorfen. Current work suggests that compound 6c may be developed as a new herbicide candidate in fields.
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