Abstract
A series of novel methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates were designed by active substructure combination. The title compounds were synthesized using a one-pot route from l-cysteine methyl ester hydrochloride, acyl chloride, and ketones. All compounds were characterized by IR, 1H NMR, 13C NMR, and HRMS. The structure of 4q was determined by X-ray crystallography. The biological tests showed that the title compounds protected maize from chlorimuron-ethyl injury to some extent. The ALS activity assay showed that the title compounds increased the ALS activity of maize inhibited by chlorimuron-ethyl. Molecular docking modeling demonstrated that Compound 4e competed against chlorimuron-ethyl to combine with the herbicide target enzyme active site, causing the herbicide to be ineffective.
Highlights
Acetolactate synthase (ALS) is an essential enzyme in the biosynthesis of branched-chain amino acids
ALS-inhibiting herbicides prevent the synthesis of isoleucine, leucine, and valine, resulting in subsequent weed death [2]
Complete details of the synthesis of methyl (R)-N-benzoyl/dichloroacetylthiazolidine-4-carboxylates from simple materials are presented in this paper
Summary
Acetolactate synthase (ALS) is an essential enzyme in the biosynthesis of branched-chain amino acids It is the target of ALS-inhibiting herbicides, including imidazolinone, sulfonylurea, sulfonylamino-carbonyl-triazolinone, triazolopyrimidine, and pyrimidinyl-thiobenzoate herbicides [1]. ALS-inhibiting herbicides prevent the synthesis of isoleucine, leucine, and valine, resulting in subsequent weed death [2]. Chlorimuron-ethyl treatments have been reported to cause phytotoxicity in beans, leading to reduced plant height and shoot dry matter [6]. Residues of this herbicide in soil may inhibit the growth of succeeding crops, such as maize [7]. In addition to these methods, herbicide safeners, a class of agrochemicals that can reduce the negative effects of a herbicide on crops, have been commercialized [9,10]
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