Design, Synthesis, and Biological Activity of Oxime Ether Strobilurin Derivatives Containing Indole Moiety as Novel Fungicide

Abstract

Twenty-one novel oxime ether strobilurins containing indole moiety, which employed an indole group to stabilize the E-styryl group in Enoxastrobin, were designed and synthesized. The biological assay indicated that most compounds exhibited potent fungicidal activities. The structure-activity relationship study demonstrated that the synthesized methyl 3-methoxypropenoate oxime ethers 7b-e exhibited remarkably high activities among all the synthesized oxime ether compounds 7. Moreover, the fungicidal activities of methyl α-(methoxyimino)benzeneacetate oxime ethers compounds 7f-i and N-methoxy-carbamic acid methyl esters compounds 7j-m showed significant differences compared to the corresponding products of ammonolysis.

Friedel‐Crafts dealkylation reaction mediated by a stereoselective proton transfer in the fragmentation of protonated cyclic indolyl α‐amino esters

“…Indole is one of the most important natural chemical templates occurring in various biologically active molecules and it has been proved to be antiviral, antioxidant, antiproliferative, etc. [1][2][3][4][5][6] As a unique but unnatural scaffold for peptides and peptidomimetics, optically active cyclic α-amino acids with indole functionalization have attracted considerable attention. [7][8][9][10][11][12][13] Recently, Jia and co-workers [14] have successfully synthesized a series of indole-functionalized chiral cyclic α-amino esters by a catalytic asymmetric Friedel-Crafts alkylation reaction, providing an efficient approach to chiral α-tetrasubstituted indolic α-amino acids.…”

Natural Compound-Derived Cytochrome bc1 Complex Inhibitors as Antifungal Agents

“…Afterward, they prepared new oxime ethers featuring heterocyclic moieties, which could drive some physicochemical properties, such as lipophilicity and solubility, toward the optimal balanced range for uptake and bioavailability. In particular, benzothiophene, benzofuran, and indole analogs were developed ( Figure 5 ) [ 12 , 13 , 14 ].…”

Synthesis, Herbicidal Evaluation, and Structure-Activity Relationship of Benzophenone Oxime Ether Derivatives

“…A few pyrazole oxime ether derivatives exhibited both good acaricidal and insecticidal activities [14][15][16]. More recently, a series of benzofuransubstituted oxime ethers were identified to possess good to excellent fungicidal activities by Xie et al [17,18].…”

“…However, very few results on the herbicidal activities of oxime ether compound were reported [19]. In this paper, a series of aryl oxime ether compounds with tertiary amino groups which are conducive to enhancing environmental compatibility [17,20] were designed and synthesized. The herbicidal activities of these compounds on Oryza sativa, Sorghum sudanense, Brassica chinensis, and Amaranthus mangostanus L. were investigated.…”