Design, Synthesis and Evaluation of Novel Trichloromethyl Dichlorophenyl Triazole Derivatives as Potential Safener

Abstract

The dominance of safener can unite with herbicides acquiring the efficient protection of crop and qualifying control of weeds in agricultural fields. In order to solve the crop toxicity problem and exploit the novel potential safener for fenoxaprop-P-ethyl herbicide, a series of trichloromethyl dichlorobenzene triazole derivatives were designed and synthesized by the principle of active subunit combination. A total of 21 novel substituted trichloromethyl dichlorobenzene triazole compounds were synthesized by substituted aminophenol and amino alcohol derivatives as the starting materials, using cyclization and acylation. All the compounds were unambiguously characterized by IR, 1H-NMR, 13C-NMR, and HRMS. A greenhouse bioassay indicated that most of the title compounds could protect wheat from injury caused by fenoxaprop-P-ethyl at varying degrees, in which compound 5o exhibited excellent safener activity at a concentration of 10 μmol/L and was superior to the commercialized compound fenchlorazole. A structure–activity relationship for the novel compounds was determined, which demonstrated that those compounds containing benzoxazine groups showed better activity than that of oxazole-substituted compounds. Introducing a benzoxazine fragment and electron-donating group to specific positions could improve or maintain the safener activity for wheat against attack by the herbicide fenoxaprop-P-ethyl. A molecular docking model suggested that a potential mechanism between 5o and fenoxaprop-P-ethyl is associated with the detoxication of the herbicide. Results from the present work revealed that compound 5o exhibited good crop safener activities toward wheat and could be a promising candidate structure for further research on wheat protection.

Safeners Improve Maize Tolerance under Herbicide Toxicity Stress by Increasing the Activity of Enzymes in Vivo

“…The maximum velocity (V max ) and Michaelis constant (K m ) of GST were calculated by linear regression of a Lineweaver−Burk plot. 9 V max of this process was decreased, while K m was increased upon treatment with TM. V max was promoted by 11.3 and 29.6% after treatment with compounds 11 and 16 compared to the control, and K m was reduced by 28.4 and 51.9%, respectively.…”

“…These results are in agreement with previous studies, indicating that safeners significantly change the affinity of GST to substrate. 9,35,46 GSH Content. GSH is a molecule specifically beneficial to crops through its participation in many plant functions (such as protein synthesis, oxidative stress, toxic compound detoxification, etc.).…”

“…Safeners are applied to reduce crop damage without lowering herbicide efficacies toward weeds. , They act by enhancing detoxification in the target crops without affecting weed sensitivity . The fortuitous discovery of the 2,4-dichlorophenoxyacetic acid action toward tomatoes being restricted by a 2,4,6-trichloro analogue lead researchers to conduct further studies of herbicide safeners.…”

Design, Synthesis, and Biological Activity of Novel Diazabicyclo Derivatives as Safeners

“…Herbicide safeners selectively protect crops from certain herbicides without affecting weed control effectiveness. , Since the first phenomenon of herbicide safening was discovered, the mechanisms of action of safeners have received considerable attention. Nevertheless, as a result of the complexity of the interactions between the safeners and the molecular mechanisms and the expression of the enzyme, there is no conclusive mechanism explaining action of the available safeners. , It is widely accepted that safeners can improve crop metabolism and detoxification by upregulating cytochrome P450 monooxygenases (CYPs), glutathione S -transferases (GSTs), glutathione (GSH), and ATP-binding casette (ABC) transporter proteins that detoxify herbicides. − The use of a suitable safener can reduce or eliminate herbicide damage to crops without affecting the herbicidal activity. As a result, it is highly urgent to develop new safeners to provide new solutions to weed control problems.…”

Synthesis of Novel 6-Aryloxy-4-chloro-2-phenylpyrimidines as Fungicides and Herbicide Safeners

“… 10 , 13 − 17 However, the widespread application of some commercial pyrimidine fungicide agents led to the development of resistance. 18 − 20 For example, the destructive plant pathogen Phytophthora capsici has developed great resistance to azoxystrobin in southern China. 21 Hence, the design and development of novel pyrimidine derivatives with promising fungicidal activities are required.…”