L-香芹酮基磺酸肟酯化合物的合成及其抑菌活性

doi:10.3969/j.issn.0253-2417.2024.01.006

摘要/Abstract

摘要：

以L-香芹酮(1)为原料，经盐酸羟胺肟化和O-磺酰化反应，合成得到23个未见文献报道的L-香芹酮基磺酸肟酯类化合物3a~3w，并通过¹H NMR、¹³C NMR、FT-IR和HRMS对目标化合物的结构进行了表征。采用琼脂稀释法测试了目标化合物对8种植物病原菌的抑制活性。结果表明：在质量浓度50 mg/L时，目标化合物对所测试的8种植物病原菌均有一定的抑菌活性，其中化合物3b(R=o-FPh)、3c(R=m-FPh)和3h(R=p-ClPh)对苹果轮纹病菌的抑制率分别为76.7%、75.9%和78.3%(均为B级活性水平)，均优于阳性对照百菌清；化合物3h对黄瓜枯萎病菌、苹果轮纹病菌、玉米小斑病菌和西瓜炭疽病菌的抑制率分别为78.4%、78.3%、82.2%和78.8%(均为B级活性水平)，具有一定的广谱抑菌活性；化合物3b对苹果轮纹病菌、玉米小斑病菌和西瓜炭疽病菌的抑制率分别为76.7%、77.5%和78.6%(均为B级活性水平)，也具有一定的广谱抑菌活性。

关键词: L-香芹酮, 磺酸肟酯, 抑菌活性, 合成

Abstract:

23 novel L-carvone-derived oxime sulfonate compounds 3a-3w were synthesized through hydroxylamine hydrochloride oximation and o-sulfonylation reactions using L-carvone(1) as the starting material. The structures of the target compounds were characterized by ¹H NMR, ¹³C NMR, FT-IR and HRMS. The antifungal activities of the target compounds against 8 tested plant pathogens were evaluated by agar dilution method. The results showed that the target compounds exhibited certain antifungal activities against the tested plant pathogens at the mass concentration of 50 mg/L. Among them, compounds 3b(R=o-FPh), 3c(R=m-FPh) and 3h(R=p-ClPh) had inhibition rates against Physalospora piricola of 76.7%, 75.9%, and 78.3%(all in B-class activity level), which were better than that of the positive control chlorothalonil. Compound 3h displayed certain broad-spectrum antifungal activity owing to its good inhibition rates of 78.4%, 78.3%, 82.2%, and 78.8%, against Fusarium oxysporum f. sp. cucumerinum, Physalospora piricola, Bipolaris maydis, and Colleterichum orbicalare, respectively(all in B-class activity level). Compound 3b also displayed certain broad-spectrum antifungal activity owing to its good inhibition rates of 76.7%, 77.5%, and 78.6%, against P. piricola, B. maydis, and C. orbicalare, respectively(all in B-class activity level).

Key words: L-carvone, oxime sulfonate, antifungal activity, synthesis

中图分类号:

TQ351

蒙玉培, 段文贵, 林桂汕, 张文静, 吴凯越. L-香芹酮基磺酸肟酯化合物的合成及其抑菌活性[J]. 林产化学与工业, 2024, 44(1): 41-50.

Yupei MENG, Wengui DUAN, Guishan LIN, Wenjing ZHANG, Kaiyue WU. Synthesis and Antifungal Activity of L-Carvone-derived Oxime Sulfonate Compounds[J]. Chemistry and Industry of Forest Products, 2024, 44(1): 41-50.

图/表 3

图1

图2

表1

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化合物 compound	抑制率inhibitory rates/%
化合物 compound	黄瓜枯萎病菌 F. oxysporum f. sp. cucumerinum	花生褐斑病菌 C. arachidicola	苹果轮纹病菌 P. piricola	番茄早疫病菌 A. solani	小麦赤霉病菌 G. zeae	水稻纹枯病菌 R. solani	玉米小斑病菌 B. myadis	西瓜炭疽病菌 C. orbiculare
3a	58.8	57.6	37.8	40.0	30.0	38.9	52.5	78.6
3b	58.8	33.8	76.7	55.0	30.0	56.1	77.5	78.6
3c	20.5	35.0	75.9	24.3	26.7	58.8	21.1	22.5
3d	17.4	63.8	31.4	67.1	65.6	14.7	26.4	31.4
3e	15.3	35.0	56.3	24.3	43.3	34.4	21.1	28.8
3f	31.1	41.3	46.6	31.4	43.3	32.0	15.6	38.8
3g	25.8	22.5	36.8	17.1	26.7	19.8	43.3	28.8
3h	78.4	41.3	78.3	38.6	21.1	22.2	82.2	78.8
3i	20.5	22.5	58.8	31.4	32.2	17.3	21.1	28.8
3j	58.8	57.6	0	30.0	30.0	42.9	45.0	58.6
3k	24.8	67.7	36.8	63.6	51.7	20.6	30.0	35.0
3l	46.6	33.8	21.1	30.0	0	23.2	37.5	35.7
3m	15.3	35.0	34.4	24.3	32.2	17.3	21.1	28.8
3n	43.3	67.7	63.6	70.7	51.7	21.8	48.2	49.3
3o	46.8	28.8	34.4	24.3	32.2	17.3	15.6	35.0
3p	25.8	28.8	66.1	17.1	43.3	22.2	21.1	35.0
3q	46.6	0	26.7	55.0	30.0	16.6	55.0	64.3
3r	41.6	28.8	41.7	31.4	26.7	22.2	21.1	16.3
3s	15.3	22.5	71.0	17.1	37.8	19.8	21.1	16.3
3t	52.1	60.0	56.3	52.9	60.0	56.3	48.9	53.8
3u	15.3	41.3	58.8	31.4	15.6	22.2	21.1	16.3
3v	58.8	19.5	48.9	30.0	30.0	36.3	57.5	64.3
3w	15.3	28.8	41.7	13.6	32.2	22.2	15.6	16.3
百菌清 chlorothalonil	100.0	73.3	75.0	73.9	73.1	96.1	90.4	91.3

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