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Application of validamycin ester in preparation of sclerotinia sclerotiorum inhibitor

A technology of Sclerotinia sclerotiorum and ester compounds, which can be applied in the application, fungicides, biocides and other directions, and can solve the problems of poor inhibitory activity and the like

Active Publication Date: 2021-08-31
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Studies have shown that Jinggangmycin A and Jinggang hydroxylamine A have poor inhibitory activity against Sclerotinia sclerotiorum

Method used

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  • Application of validamycin ester in preparation of sclerotinia sclerotiorum inhibitor
  • Application of validamycin ester in preparation of sclerotinia sclerotiorum inhibitor
  • Application of validamycin ester in preparation of sclerotinia sclerotiorum inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the preparation of acetic acid Jinggang hydroxylamine A ester (compound a, one ester):

[0044]Add 1.5mmol (90.075mg) acetic acid, 60mg Novozym 435, 0.6g 4A°molecular sieve to 21mL (0.5mmol Jinggang Hydroxylamine A) saturated solution, react in a constant temperature oscillator at 50°C, add 0.5mmol Jinggang Hydroxylamine A powder for 24 hours, The reaction was carried out for 40h. After the reaction, the reaction solution was centrifuged to remove the immobilized enzyme and molecular sieve, concentrated by evaporation, extracted with n-butanol, concentrated organic phase, and separated on a silica gel column. The eluent was n-propanol: acetic acid = 2:1. The eluent was detected by TLC, the developing agent was n-propanol:water:acetic acid=4:1:1, and the developing agent was ninhydrin solution and iodine vapor.

[0045] 1 H NMR (600MHz, DMSO) δ5.75(s, 1H), 4.54(d, J=94.3Hz, 2H), 4.15(d, J=7.7Hz, 2H), 3.97(s, 1H), 3.77–3.45 (m,4H),3.40(d,J=14.2Hz,3H),3.33...

Embodiment 2

[0047] Embodiment 2: the preparation of Jinggang hydroxylamine propionic acid ester (compound b, one ester):

[0048] Add 1.5mmol (111mg) propionic acid, 60mg Novozym 435, 0.6g 4A° molecular sieve to 21mL (0.5mmol Jinggang Hydroxylamine A) saturated solution, react in a constant temperature oscillator at 50°C, add 0.5mmol Jinggang Hydroxylamine A powder for 24 hours, The reaction was carried out for 40h. After the reaction, the reaction solution was centrifuged to remove the immobilized enzyme and molecular sieve, concentrated by evaporation, extracted with n-butanol, concentrated organic phase, and separated on a silica gel column. The eluent was n-propanol: acetic acid = 4:1. The eluent was detected by TLC, the developing agent was n-propanol:water:acetic acid=4:1:1, and the developing agent was ninhydrin solution and iodine vapor.

[0049] 1 H NMR(600MHz,DMSO)δ5.75(s,1H),4.65(s,1H),4.46(s,1H),4.18(d,J=7.7Hz,2H),3.97(s,1H),3.72 (d,J=11.0Hz,4H),3.48(s,1H),3.38(s,2H),3.33(s...

Embodiment 3

[0051] Embodiment 3: the preparation (compound c, monoester) of butyric acid jinggang hydroxylamine A ester:

[0052] Add 1.5mmol (132mg) butyric acid, 60mg Novozym 435, and 0.6g 4A°molecular sieve to 21mL (0.5mmol Jinggang Hydroxylamine A) saturated solution, react in a constant temperature oscillator at 50°C, add 0.5mmol Jinggang Hydroxylamine A powder for 24 hours, The reaction was carried out for 40h. After the reaction, the reaction solution was centrifuged to remove the immobilized enzyme and molecular sieve, concentrated by evaporation, extracted with n-butanol, concentrated organic phase, and separated on a silica gel column. The eluent was n-propanol: acetic acid = 4:1. The eluent was detected by TLC, the developing agent was n-propanol:water:acetic acid=4:1:1, and the developing agent was ninhydrin solution and iodine vapor.

[0053] 1 H NMR (600MHz, DMSO) δ4.73(d, J=13.9Hz, 2H), 4.56(s, 1H), 4.41(dd, J=9.5, 5.8Hz, 1H), 4.31(s, 1H), 3.77 (t,J=8.4Hz,1H),3.53(dd,J=1...

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Abstract

The invention provides an application of a validamycin ester in preparation of a sclerotinia sclerotiorum inhibitor. The structure of the validamycin ester is represented by formula shown in the specification. In the formula, R8 is RCO-, and R1-R7 are H; and R is one of the following: (1) CH3(CH2)7CH=CH(CH2)7-; (2) CH3(CH2)4CH=CHCH2CH=CH(CH2)7-; (3) CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7-; (4) CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4-; (5) phenyl; (6) CH3(CH2)13-; and (7) CH3(CH2)20-. In the groups shown in (1)-(4), double bonds are all cis-structures. The validamycin ester provided by the invention has a good inhibition effect on the sclerotinia sclerotiorum inhibitor.

Description

technical field [0001] The invention relates to the application of a class of Jinggang esters in the preparation of inhibitors of Sclerotinia sclerotiorum. [0002] technical background [0003] Rapeseed is the main oil crop in China. Sclerotinia sclerotiorum is one of the important diseases in rapeseed production. The incidence rate of perennial plants is as high as 10% to 30%, and the serious ones reach more than 80%. Diseased plants generally reduce yield by 10% to 70%. Therefore, the research and development of inhibitors of Sclerotinia sclerotiorum is of great significance. [0004] As a microbial-derived antibiotic, Validamycin has a good control effect on rice sheath blight and is one of the most commonly used and effective pesticides. It has long-lasting efficacy, low toxicity, high safety factor, and is harmless to humans and animals. It is one of the pesticides with the largest application area and the lowest cost per mu in my country. It is a kind of weakly basic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N37/02A01N37/04A01N37/06A01N37/10A01P3/00C12P13/00C07C219/24
CPCA01N37/02A01N37/04A01N37/06A01N37/10C12P13/001C07C219/24C07C2601/14C07C2601/16
Inventor 陆跃乐朱林江蔡晓青范永仙陈小龙
Owner ZHEJIANG UNIV OF TECH