Controllable Soil Degradation Rate of 5-Substituted Sulfonylurea Herbicides as Novel AHAS Inhibitors

Zhou, Shuang-Shuang; Meng, Fansen; Hua, Xuewen; Li, Yonghong; Liu, Bin; Wang, Baolei; Chen, Jie; Chen, Anliang; Li, Zhengming

doi:10.1021/acs.jafc.9b06679

Cited by 15 publications

(21 citation statements)

References 31 publications

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“…The previous studies reported that the primary target of chlorsulfuron and other sulphonylurea herbicides is acetolactate synthase, the enzyme specifically involved in branched-chain amino acids biosynthesis (Zhou et al 2007, Orcaray et al 2010. But, there was no significant decrease of branched-chain amino acids under chlorsulfuron stress in maize.…”

Section: Discussionmentioning

confidence: 95%

“…(2-chloro-N- [(4-methoxy-6-methyl-1,3, 5-triazine-2-yl) aminocarbonyl]-benzene-sulfonamide) is a selective, systemic post-emergence herbicide. It was the first sulfonylurea herbicide approved in the United States (Zhou et al 2020), and globally, it was one of the most commonly used herbicides of its type for removing broadleaf weeds and other weedy annuals in wheat and barley fields. According to existing reports, the primary target of chlorsulfuron and other sulfonylurea herbicides is acetolacetate synthase (ALS), the enzyme specific to branched-chained amino acid biosynthesis (Fan 2003).…”

Section: Chlorsulfuronmentioning

confidence: 99%

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Effects of chlorsulfuron and cadmium on metabolites of maize seedlings

Zhao¹,

Wang²,

Zhang³

et al. 2021

Biologia plant.

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The impact of persisting herbicide residues on succeeding crops is of great concern to farmers because even the presence of very low concentrations can inhibit growth of crop and cause crop reduction. Furthermore, wastewater irrigation can lead to cadmium accumulation in soils. Thus, the co-occurrence of low amounts of herbicide residues and cadmium within agricultural fields are difficult to avoid. How the combination of these two pollutants affect plant metabolites remains to be elucidated and thus warrants investigation. Maize seeds were planted in soil that had been sprayed with chlorsulfuron and Cd, then we studied the effects of exposure to the herbicide chlorsulfuron (0.001, 0.003, 0.005, 0.008, and 0.010 mg kg -1 ) and cadmium (as 5.0 mg kg -1 CdCl2) on maize seedlings by utilizing nuclear magnetic resonance (NMR) after 21 d. Principle component analysis of 1 H NMR spectra clearly discriminated between control and treatment groups. Compared with chlorsulfuron-only treatments, treatments using both contaminants showed higher content of phenolic acids, aspartic acid, choline, β-galactose, and α-glucose in the seedlings. Contrary to previous reports, we found larger pools of branched-chain amino acids in seedlings exposed to chlorsulfuron and CdCl2. These findings indicate that CdCl2 did not aggravate the effects of chlorsulfuron on maize seedlings metabolites. CdCl2 elicited significant changes in plant metabolism at a concentration that did not impair plant growth. Moreover, chlorsulfuron did not inhibit branched chain amino acid synthesis.

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Section: Discussionmentioning

confidence: 95%

Section: Chlorsulfuronmentioning

confidence: 99%

Effects of chlorsulfuron and cadmium on metabolites of maize seedlings

Zhao¹,

Wang²,

Zhang³

et al. 2021

Biologia plant.

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“…4 Its inhibition interrupts the catalytic cycle and protein synthesis in the meristem by blocking cell division, resulting in the inhibition of growth and subsequent death of plants. 5 The antifungal property provides sulfonylureas the potential of being used as antifungal additives in the silage process. Forage is a vegetal material used for animal feed and, during the silage process, it may be affected by fungi.…”

Section: Introductionmentioning

confidence: 99%

Computer-Assisted Improvement of Sulfonylureas with Antifungal Properties and Limited Herbicidal Activity: Potential Application in Forage Conservation

Faria

Daré

Cunha

et al. 2022

J. Agric. Food Chem.

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This work reports studies at the molecular level of a series of modified sulfonylureas to determine the chemophoric sites responsible for their antifungal and herbicidal activities. For forage conservation, high antifungal potency and low phytotoxicity are required. A molecular modeling study based on multivariate image analysis applied to quantitative structure–activity relationship (MIA-QSAR) was performed to model these properties, as well as to guide the design of new agrochemical candidates. As a result, the MIA-QSAR models were reliable, robust, and predictive; for antifungal activity, the averages of the main validation parameters were r 2 = 0.936, q 2 = 0.741, and r 2 pred = 0.720, and for herbicidal activity, the model was very predictive (r 2 pred = 0.981 and r 2 m = 0.944). From the interpretation of the MIA-plots, 46 novel sulfonylureas with likely improved performance were proposed, from which 9 presented promising calculated selectivity indexes. Docking studies were performed to validate the QSAR predictions and to understand the interaction mode of the proposed ligands with the acetohydroxyacid synthase enzyme.

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“…Numerous herbicides, with approximately 20 modes of actions (MOA), have been discovered and marketed from the 1950s to the 1990s . Examples of herbicidal inhibiting actions include protoporphyrinogen oxidase (PPO), , acetohydroxyacid synthase (AHAS), , acetyl-CoA carboxylase (ACCase), 4-hydroxyphenylpyruvatedioxygenase (HPPD), − and many others.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Herbicidal Activity of Thioether Containing 1,2,4-Triazole Schiff Bases as Transketolase Inhibitors

Wang

Yang

Huo

et al. 2021

J. Agric. Food Chem.

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Transketolase (TK) represents a potential target for novel herbicide development. To discover novel TK inhibitors with potency against resistant weeds, 36 thioether compounds containing 1,2,4-triazole Schiff bases were designed and synthesized for herbicidal activity evaluation. The results demonstrated that compounds 5av and 5aw provided excellent weed control with inhibition of over 90% against the tested weeds, even at concentrations as low as 100 mg/L in vitro. In addition, compounds 5av and 5aw exhibited higher postemergence herbicidal activity than all of the positive controls against the tested weeds at 50−90 g [active ingredient (ai)]/ha in a greenhouse, while being safe for crops of maize and wheat at 90 g (ai)/ha. Fluorescent binding experiments of At TK indicated that compounds 5av and 5aw had strong TK inhibitory activity and could tightly bind with the enzyme At TK. Also, molecular docking analyses revealed that the structures of compounds 5av and 5aw were suitable for TK inhibitory activity. Taken together, these results suggested that compounds 5av and 5aw were promising herbicide candidates for weed control in wheat and maize fields targeting TK.

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Controllable Soil Degradation Rate of 5-Substituted Sulfonylurea Herbicides as Novel AHAS Inhibitors

Cited by 15 publications

References 31 publications

Effects of chlorsulfuron and cadmium on metabolites of maize seedlings

Effects of chlorsulfuron and cadmium on metabolites of maize seedlings

Computer-Assisted Improvement of Sulfonylureas with Antifungal Properties and Limited Herbicidal Activity: Potential Application in Forage Conservation

Design, Synthesis, and Herbicidal Activity of Thioether Containing 1,2,4-Triazole Schiff Bases as Transketolase Inhibitors

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