Design, Synthesis, and Herbicidal Activity of Novel Diphenyl Ether Derivatives Containing Fast Degrading Tetrahydrophthalimide

Abstract

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.

Rational Design, Synthesis and Evaluation of Indole Nitrogen Hybrids as Photosystem II Inhibitors

“…Intensive efforts aimed at developing new herbicidal compounds or modifying existing ones are ongoing (9)(10)(11)(12)(13)(14)(15)(16). A wide variety of chemical compounds have demonstrated plant management activity including the indole derivatives 1 and 2 (12) which demonstrate photosynthesis inhibitory activity as well as compounds 3 (17) and 4 (18) which are plant growth inhibitors (Fig.…”

Crystal structure of 2-(3,6-dimethyl-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)-2-oxoethyl acetate, C14H17NO4

“…Moreover, benzoxazine derivatives were also used as medical or pharmaceutical intermediates in the synthesis of compounds with therapeutic interest [11]. In continuation of our effort to search for novel N-containing heterocyclic compounds with excellent bioactivities [12][13][14][15][16], herein we reported the synthesis and the crystal structure of substituted benzoxazine.…”

Discovery of novel arylthioacetic acid derivatives as 4‐hydroxyphenylpyruvate dioxygenase inhibitors

“…13 Studies over the past decades have provided important information on interactions between HPPD enzymes and HPPD inhibitors: 1,3-dicarbonyl and aromatic moieties are an indispensable pharmacophore for potent HPPD inhibition. Many researches [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] in HPPD inhibitors indicated that modification of the aromatic moieties is an effective way to get new derivatives with excellent weed control.…”