Design, Synthesis, Crystal Structure, and Fungicidal Activity of L-Carvone Derivatives Containing an Oxime Ester Moiety

Abstract

L-Carvone is a natural product with fungicidal activity, which can be used as a lead compound for screening new fungicides. A series of L-carvone derivatives containing an oxime ester moiety were synthesized by splicing active substructure strategy with L-carvone as the lead compound. The structures of the L-carvone derivatives were characterized by IR, 1 H NMR, 13 C NMR and HRMS analyses. The antifungal activities of these compounds were evaluated against five plant pathogenic fungi, namely Sclerotinia sclerotiorum, Fusarium graminearum, Pyricularia grisea, Fusariwn oxysporum and Thanatephorus cucumeris. The results indicated that most of the compounds showed good antifungal activities. Among them, (E)-2methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one O-(4-ethylbenzoyl)oxime (4e) had the best fungicidal activity against Fusarium graminearum (EC50＝5.07 mg/L), and (S,E)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one O-(3-methylbenzoyl)oxime (4b) had the best fungicidal activity against Sclerotinia sclerotiorum, (EC50＝18.84 mg/L), which were better than the commercial fungicide enestroburin. Therefore, L-carvone derivatives have the potential to develop new fungicides.

An Effective and Promising Strategy for Plant Protection: Synthesis of L-Carvone-Based Thiazolinone–Hydrazone/Nanochitosan Complexes with Antifungal Activity and Sustained Releasing Performance

“…As a natural and sustainable forest product-bearing carbonyl, carvone has been found in the seed essential oils of Anethum graveolens [9], Mentha spicata [10,11], and Carum 2 of 12 carvi [12], and its diverse pharmacological activities have been reported [13], such as antifungal [14][15][16][17], antioxidant [18], anti-inflammatory [19], and anticancer activities [20,21]. Moreover, it was discovered that the original skeleton of carvone could serve as an available pharmacophore for bioactive compounds [22][23][24][25][26]. Moreover, thiazolinone-hydrazone derivatives showed various biological activities, including antifungal [27], antitrypanosomal [28,29], insecticidal [30,31], antiproliferative [32], and α-glucosidase inhibition activities [33].…”

Rational design and synthesis of l-carvone-derived 4-methyl-1,2,4-triazole-thioether/nanochitosan complexes as potent nanopesticides for sustainable and efficient herbicidal application

“…[3][4][5][6] Carvone, a chiral ketone-bearing monocyclic monoterpene structure, is naturally found in various plant essential oils, 7 such as spearmint (Mentha spicata), 8,9 caraway (Carum carvi), 10 and dill (Anethum graveolens), 11 and it has been applied as a building block to construct some bioactive compounds. 12,13 Besides, according to the reported literature, [14][15][16] 1,2,4-triazole-thioether moiety could serve as a promising pharmacophore for the design, discovery, and development of new green herbicides. The study of Wang et al 14 revealed that transketolase (TK) was one of the potential biological targets for those herbicidal compounds containing a 1,2,4-triazole-thioether structure.…”

Functional Study on Cytochrome P450 in Response to L(−)-Carvone Stress in Bursaphelenchus xylophilus

“…L(−)-carvone, a monoterpene insecticide, is environmentally friendly and effective in controlling pests [ 7 ]. Thus, carvone has been widely used for many years as an insecticide, fungicide, antioxidant, and plant growth regulator [ 8 , 9 , 10 , 11 ]. Carvone is widely used as a plant essential oil in the treatment of parasitic nematodes.…”