莰烯醛肟及其烃基醚衍生物的合成与抑菌活性研究

doi:10.3969/j.issn.0253-2417.2020.01.011

Abstract

Abstract:

ω-Formylcamphene oxime (2) was synthesized by the reaction of formylcamphene (1) with hydroxylamine hydrochloride.and then reacted with halohydrocarbon to synthesize five ω-formylcamphene oxime alkyl ether derivatives, such as ω-formylcamphene oxime ethyl ether (3a), ω-formylcamphene oxime propyl ether (3b), ω-formylcamphene oxime butyl ether (3c), ω-formylcamphene oxime n-pentyl ethers (3d), ω-formylcamphene oxime benzyl ethe (3e). Their structures were characterized by FI-IR, MS and NMR. The mycelium growth rate method was used to test the inhibitory effects of ω-formylcamphene oxime and its hydrocarbyl ethers on 12 kindsof plant pathogenic fungi. The results showed that the products had certain inhibitory effects on 12 kinds of plant pathogenic fungi, among which ω-formylcamphene oxime had the best activity and the best inhibitory against Colletotrichum gloeosporioides, EC₅₀ was 39.25 mg/L. The EC₅₀ values of Thanatephoruscu cumeris, Phomopsis sp., Fusarium avenaceum and Ceratosphaeria phyllostachydis sp. nov. were 40-50 mg/L. Under the concentration of 500 mg/L, ω-formylcamphene oxime completely inhibited 9 plant pathogenic fungi such as Thanatephorus cucumeris, and the inhibitory rates of ω-formylcamphene oxime against Sphaeropsi ssapinea and Fusicoccum aesuli were over 97%. When the medicament concentration of ω-formylcamphene oxime lowered, the inhibitory rates on most plant pathogenic fungi were still higher than that of chlorothalonil at 500 mg/L. Although the antibacteria activity of ω-formylcamphene oxime hydrocarbyl ethers was lower than that of ω-formylcamphene oxime, but the inhibitory rates of ω-formylcamphene oxime hydrocarbyl ethers against Ceratosphaeria phyllostachydis, Alternaria kikuchiana and Fusarium avenaceum were generally higher than that of chlorothalonil.

Key words: formylcamphene, ω-formylcamphene oxime, phase transfer catalysis, structural analysis, antibacterial activity

CLC Number:

TQ351
O621

Xuezhen FENG,Zhuanquan XIAO,Shangxing CHEN,Guorong FAN,Shengliang LIAO,Zongde WANG. Synthesis and Antibacterial Activity of ω-formylcamphene Oxime and Its Hydrocarbyl Ethers Derivatives[J]. Chemistry and Industry of Forest Products, 2020, 40(1): 77-83.

Figures/Tables 3

Fig.1

Table 1

Table 2

References 19

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化合物 compounds	质量浓度/(mg·L^-1) mass concn.	A	B	C	D	E	F	G	H	J	K	L	M
	500	100	100	100	100	100	100	100	100	100	98.4	97.0	75.7
	250	98.3	95.4	83.6	98.1	98.7	86.2	97.6	98.0	98.5	79.1	73.4	65.3
2	125	85.5	61.3	44.8	84.6	96.4	61.9	94.3	85.9	97.7	56.0	58.4	39.0
	62.5	55.2	27.3	13.4	60.4	66.7	41.8	83.1	29.6	67.6	44.9	44.5	18.3
	31.25	45.8	23.0	8.4	48.1	31.3	30.7	45.4	26.1	34.5	37.5	34.5	12.0
3a	500	82.9	75.2	80.9	21.0	55.3	59.2	11.7	39.5	65.8	79.8	12.7	38.1
3b	500	88.2	79.3	77.3	38.0	69.9	69.5	22.5	30.2	87.2	76.8	30.3	29.6
3c	500	78.4	60.0	52.9	34.2	62.3	52.3	34.3	37.8	92.2	63.1	16.9	29.4
3d	500	83.3	53.4	53.5	38.1	60.2	51.2	24.5	38.4	90.5	36.8	63.7	36.8
3e	500	100	72.8	93.7	80.3	58.1	43.7	77.6	83.5	79.4	96	69.7	84.6
百菌清chlorothalonil	500	100	72.8	93.7	80.2	58.1	43.7	77.4	83.5	79.4	96.0	69.7	84.6

菌种 strain	毒力回归方程 toxic regression equation	相关系数 correlation coefficient	EC₅₀/ (mg·L^-1)	置信区间 confidence interval
A	y₁=-1.8578+4.0528x	0.9307	49.21	26.97~89.81
B	y₂=-3.4635+4.5731x	0.9179	70.91	40.77~123.40
C	y₃=-3.4635+4.9308x	0.9060	91.32	52.99~157.38
D	y₄=-0.8558+3.6406x	0.9279	40.59	23.71~69.51
E	y₅=-1.8295+4.1287x	0.9706	45.10	32.88~61.85
F	y₆=-2.4353+4.0877x	0.8675	65.91	30.83~140.90
G	y₇=-0.9567+3.7373x	0.9290	39.25	19.80~77.79
H	y₈=-3.2710+4.6076x	0.9481	62.39	39.54~98.44
J	y₉=-1.8704+4.1561x	0.9583	44.99	27.90~72.54
K	y₁₀=1.4468+1.9480x	0.9293	66.68	39.50~112.55
L	y₁₁=1.7286+1.7681x	0.9409	70.83	44.65~112.37
M	y₁₂=1.2351+1.6745x	0.9897	117.17	149.37~210.13

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Synthesis and Antibacterial Activity of ω-formylcamphene Oxime and Its Hydrocarbyl Ethers Derivatives

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