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Application of phenazine‑1‑carboxamide modified compound 18‑3 in inhibiting Sclerotinia sclerotiorum

A technology of Sclerotinia sclerotiorum and Sclerotinia sclerotiorum, which is applied in application, bactericide, biocide, etc., can solve the problems of rapeseed thousand-grain weight reduction, early plant withering, and destruction of ecological balance, and achieve good inhibitory effect and inhibitory effect Strong, less resistant effect

Active Publication Date: 2018-01-26
HUNAN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The occurrence of the disease will cause a decrease in the thousand-grain weight of rapeseed, a decrease in siliques, shriveled seeds, and early withering of plants, etc., resulting in a 10%-50% or even 80% reduction in rapeseed yield, which will bring huge losses to production.
[0003] The method of preventing and treating Sclerotinia sclerotiorum in production mainly relies on chemical control. The chemical pesticides that can be used to control Sclerotinia sclerotiorum include ergosterol biosynthesis inhibitors such as imidamide and tebuconazole; benzimidazoles such as carbendazim and formazan Base tobuzin; substituted benzenes such as chlorothalonil; dicarboximides such as sclerotin, procymidone, iprodione, vinclozolin; triazoles such as propiconazole; carbamates such as B However, the long-term single use of large quantities of chemical pesticides not only pollutes the environment and destroys the ecological balance, but also easily leads to the development of drug resistance of bacteria

Method used

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  • Application of phenazine‑1‑carboxamide modified compound 18‑3 in inhibiting Sclerotinia sclerotiorum
  • Application of phenazine‑1‑carboxamide modified compound 18‑3 in inhibiting Sclerotinia sclerotiorum
  • Application of phenazine‑1‑carboxamide modified compound 18‑3 in inhibiting Sclerotinia sclerotiorum

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1 Preparation of phenazine-1-carboxamide transformation compound 18-3

[0015] Improve the synthesis of compound 18-3: hydrolyze phenazine-1-carboxamide under acidic conditions to generate phenazine-1-carboxylic acid; take 6.2mmol phenazine-1-carboxylic acid (1.4179g), 6.2mmol 4-benzene butylamine (1ml), 12.4mmol tris(trifluoroethoxy) boron (2.675ml) and 12.4ml acetonitrile were added in a 25ml round bottom flask, magnetically stirred, and reacted at 80°C for 24h, and after the reaction liquid was cooled, 20ml of DCM and 3ml of water, then add Amberlyst A-26(OH), Amberlyst 15, AmberliteIRA743 resin 930mg each, stir at room temperature for 30min, then add anhydrous magnesium sulfate powder to remove water, filter, use dry DCM to wash solid magnesium sulfate 3 times, Rotary evaporation gave the modified compound 18-3 with a yield of 52.64%.

Embodiment 2

[0016] Example 2 Structural identification of phenazine-1-carboxamide transformation compound 8-3

[0017] Proton spectrum (1H NMR (500MHz, CDCl3) δ11.04 (s, 54H), 9.05–8.86 (m, 56H), 8.52–7.66 (m, 363H), 7.29 (s, 10H), 7.33–7.14 (m ,15H),4.03–3.44(m,255H),3.41(d,J=3.3Hz,163H),3.35(t,J=4.6Hz,13H),2.67(s,4H),2.33(d,J= 13.9Hz, 4H), 2.18–2.01(m, 122H), 1.83(dd, J=12.6, 6.1Hz, 4H), 1.48–1.14(m, 107H), 1.74–0.78(m, 275H), 1.53–0.78 (m, 253H), 1.00 (ddd, J = 18.6, 14.5, 7.3Hz, 26H), 0.93–0.50 (m, 119H), -0.00 (s, 14H).), carbon spectrum (13C NMR (126MHz, CDCl3 )δ164.77(s),143.41(s),142.91(s),141.33(s),140.84(s),135.35(s),133.52(s),131.60(s),131.00(s),130.09( s), 129.69(s), 129.21(s), 129.02(s), 77.32(s), 77.07(s), 76.81(s), 70.94(s), 58.80(s), 37.46(s), 29.52( s).) and mass spectrometry (molecular weight: 355.17, figure 1 ) detects that the compound synthesized in the foregoing examples matches the expected target, and its molecular formula is C 23 h 21 N 3 O, the structural ...

Embodiment 3

[0019] Example 3 Phenazine-1-carboxamide transformation compound 18-3 activity determination of Sclerotinia sclerotiorum

[0020] ⑴Instruments and related materials

[0021] YJ-VS-2 ultra-clean workbench (Wuxi Yijing Purification Equipment Co., Ltd.), LDZX-30E sterilizer (Shanghai Shen'an Medical Instrument Factory), MPJ-250 incubator (Shanghai Senxin Experimental Instrument Co., Ltd.) , QHX-400B-III light incubator (Shanghai Xinmiao Medical Instrument Manufacturing Co., Ltd.), electric furnace (Beijing Zhongxing Weiye Instrument Co., Ltd.), etc., as well as measuring cylinders, glass rods, beakers, triangular flasks, rulers, pencils, label paper, Parafilm, picking needle, volumetric flask, inoculation needle, ph-101 watering can, puncher, petri dish, kitchen knife, gauze.

[0022] ⑵ medicine

[0023] The phenazine-1-carboxamide modified compound 18-3 original drug obtained in Example 1 (hereinafter referred to as modified 18-3); agar, glucose, acetone and Tween 80 were all ...

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Abstract

The invention relates to an application of a phenazine-1-carboxamide modified compound 18-3 in the inhibition of Sclerotinia sclerotiorum. The phenazine-1-carboxamide modified compound 18-3 is obtained through structure modification of phenazine-1-carboxamide used as a parent substance. The inhibition effect of the modified compound 18-3 on the Sclerotinia sclerotiorum is detected through adopting a growth rate technology, and a result shows that the modified compound 18-3 has an inhibitory effect on the strawberry gray mold, and has a higher Sclerotinia sclerotiorum inhibition effect than the parent substance phenazine-1-carboxamide, so the modified compound 18-3 can be used as a lead compound of new pesticides for controlling the Sclerotinia sclerotiorum.

Description

technical field [0001] The invention belongs to the field of pesticide creation, and particularly relates to the application of phenazine-1-carboxamide modified compound 18-3 in inhibiting Sclerotinia sclerotiorum. Background technique [0002] Rapeseed is an important oil crop in my country. The oil content of its seeds is between 33-55%, which has high economic value. Rapeseed can not only be used to extract edible oil and feed, but also has a wide range of uses in medicine, industry, food, etc. Recent research results show that my country is the largest rapeseed country in the world, with an area of ​​about 7 million hectares, and is an important rapeseed producer. Rapeseed has a long growth cycle and is often disturbed by various factors, among which Sclerotinia sclerotiorum is an important factor affecting the yield increase of rapeseed. The disease, also known as stem rot, mildew, white stalk, empty stalk, etc., is a fungal disease caused by Sclerotinia sclerotiorum,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N43/60C07D241/46A01P3/00
CPCA01N43/60C07D241/46
Inventor 张亚廖晓兰刘双清王翀
Owner HUNAN AGRICULTURAL UNIV