α-萜品烯酰基农用杀菌活性物的合成及活性研究

doi:10.3969/j.issn.0253-2417.2022.06.006

Abstract

Abstract:

Three pinene-based derivatives of dihydrocuminic amides compounds(5a-5g), dihydrocuminic oxime esters compounds(6a-6f) and dihydrocuminic acyl hydrazones compounds(8a-8f) were prepared from β-pinene. The structurs of the product were characterized by FT-IR, ¹H NMR and MS. The bactericidal activities of the obtained compounds were investigated by mycelial growth rate method. The results showed that these 19 compounds had inhibitory effects on Valsa mali, Botrytis cinerea and Phytophthora capsici, where the inhibitory effect on V. mali was stronger. The half effective mass concentration(EC₅₀) values of compounds 5a and 8e against V. mali were 10.489 and 10.810 mg/L, respectively. The results of preliminary structure-activity relationship showed that the introduction of electronegative functional groups such as halogen atoms, cyano groups and nitro groups to the compounds could significantly improve the antibacterial activity of the compounds. Among them, 5a and 8e could be used as lead compounds for further optimization study.

Key words: β-pinene, halogen containing derivatives, antifungal activity

CLC Number:

TQ35
R914.5

Xuan LI, Tingmin PAN, Yuanxiao GENG, Haiyu ZHOU, Jian LI, Yanqing GAO. Synthesis and Antifungal/Anti-oomycete of Turpentine Based Derivatives[J]. Chemistry and Industry of Forest Products, 2022, 42(6): 39-46.

Figures/Tables 5

Fig.1

Table 1

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Table 2

Fig.3

References 19

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化合物 compound	抑制率inhibitory rate/%
化合物 compound	苹果腐烂病菌 V. mali	番茄灰霉病菌 B. cinerea	辣椒疫霉 P. capsici
5a	90.6	27.9	—
5b	90.3	33.9	31.9
5c	45.6	32.0	20.0
5d	34.2	25.3	22.9
5e	30.2	22.6	56.6
5f	23.5	45.6	26.6
5g	22.4	42.8	22.3
6a	34.5	33.8	28.9
6b	50.7	34.5	27.9
6c	44.4	32.1	28.9
6d	45.6	22.1	44.4
6e	46.7	20.4	49.6
6f	47.6	25.9	12.1
8a	88.8	—	—
8b	85.9	24.1	12.9
8c	90.6	28.9	28.9
8d	87.6	27.9	32.3
8e	82.4	33.5	27.9
8f	88.9	34.7	26.3
多菌灵 carbendazim	100.0	25.9	17.4

化合物 compound	不同质量浓度下的抑制率inhibitory rate at different mass concn./%					EC₅₀/(mg·L^-1)	回归方程 regression equations	R²
化合物 compound	100 mg/L	50 mg/L	25 mg/L	12.5 mg/L	6.25 mg/L	EC₅₀/(mg·L^-1)	回归方程 regression equations	R²
5a	90.6	80.2	68.3	52.8	37.8	10.489	y=-0.318x+0.030	0.911
5b	90.3	79.5	62.7	50.4	30.0	17.016	y=-0.570x+0.033	0.903
5c	45.6	20.5	—	—	—	—	—	—
5d	34.2	—	—	—	—	—	—	—
5e	30.2	—	—	—	—	—	—	—
5f	23.5	—	—	—	—	—	—	—
5g	22.4	—	—	—	—	—	—	—
6a	34.5	—	—	—	—	—	—	—
6b	50.7	20.9	—	—	—	—	—	—
6c	44.4	33.5	—	—	—	—	—	—
6d	45.6	33.2	—	—	—	—	—	—
6e	46.7	20.5	—	—	—	—	—	—
6f	47.6	20.8	—	—	—	—	—	—
8a	82.4	69.2	56.4	45.8	35.5	21.360	y=-0.474x+0.022	0.941
8b	85.9	71.3	59.6	50.1	40.9	14.046	y=-0.319x+0.023	0.971
8c	90.6	73.2	61.1	51.2	43.0	12.198	y=-0.325x+0.027	0.992
8d	87.6	70.6	58.4	49.6	39.7	15.961	y=-0.391x+0.025	0.982
8e	90.2	75.6	62.3	52.3	42.7	10.810	y=-0.289x+0.027	0.981
8f	86.1	69.0	57.8	48.7	39.5	17.073	y=-0.395x+0.023	0.980

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Synthesis and Antifungal/Anti-oomycete of Turpentine Based Derivatives

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