Application of phenazine-1-formamide modified compound 15-1 in inhibiting Sclerotinia sclerotiorum

Abstract

The invention discloses application of a phenazine-1-formamide modified compound 15-1 in inhibiting Sclerotinia sclerotiorum. The phenazine-1-formamide modified compound 15-1 is obtained with phenazine-1-formamide as a mother substance by structural modification. According to the invention, a growth rate method is adopted to measure the inhibiting effect of the phenazine-1-formamide modified compound 15-1 on Sclerotinia sclerotiorum. The results indicate that the modified compound 15-1 has good inhibitory effect on Sclerotinia sclerotiorum, and the inhibitory effect is better than that of the mother substance phenazine-1-formamide, which indicates that the modified compound 15-1 can be used as a lead compound of new pesticides for controlling Sclerotinia rot of rape.

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 15-1 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.

[0003] 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 scle...

Examples

Embodiment 1

[0015] Example 1 Preparation of phenazine-1-carboxamide modified compound 15-1

[0016] The specific process of synthesis: hydrolyze phenazine-1-carboxamide under acidic conditions to generate phenazine-1-carboxylic acid; take 20mmol phenazine-1-carboxylic acid (0.4577g) and 200ml thionyl chloride and add it to a 500ml round bottom In the flask, a reflux reaction device (using anhydrous calcium chloride drying tube) was installed, magnetically stirred, and refluxed for 6 hours. After the reaction solution was cooled, the thionyl chloride was removed by rotary evaporation to obtain the intermediate product phenazine-1-formyl chloride. The purification is directly used in the next step reaction; the obtained phenazine-1-formyl chloride is dissolved in 200ml of dry dichloromethane (DCM), added to a 500ml dry round bottom flask, protected by nitrogen, magnetically stirred, and cooled in an ice-water bath 11.15ml of triethylamine (80mmol, 4equiv.) and 2.367g of 3-methoxy-1-propylam...

Embodiment 2

[0017] Example 2 Structural identification of modified compound 15-1

[0018] The modified compound 15-1 obtained was determined by proton nuclear magnetic resonance (1H NMR) and carbon nuclear magnetic resonance (13C NMR) techniques. Proton spectrum (1H NMR (500MHz, CDCl3) δ11.03 (s, 12H), 9.25–8.90 (m, 59H), 8.90–7.86 (m, 427H), 8.11–7.73 (m, 224H), 8.11–7.73 (m,223H),7.82(dd,J=16.5,10.4Hz,19H),7.29(s,16H),7.10–6.85(m,6H),5.86–5.75(m,8H),5.33–5.23(m ,9H),4.82(t,J=9.7Hz,9H),4.89–4.39(m,14H),4.89–4.24(m,19H),4.89–4.18(m,23H),4.89–4.07(m,29H ),4.89–4.02(m,32H),4.89–3.71(m,81H),3.68(d,J=20.8Hz,17H),3.71–3.51(m,22H),3.71–3.30(m,38H), 3.71–3.26(m,43H),3.71–3.20(m,53H),3.71–3.03(m,80H),3.71–3.05(m,80H),3.71–2.93(m,83H),3.71–2.88(m ,84H),3.71–2.81(m,85H),3.71–2.45(m,128H),3.71–2.41(m,133H),3.71–2.27(m,150H),3.71–2.17(m,155H),3.71 –2.12(m,159H),3.71–2.07(m,169H),3.71–2.01(m,175H),3.71–1.70(m,258H),3.71–1.62(m,273H),3.71–1.54(m, 292H), 3.71–1.40(m, 351H), 1.24(dd, J=37.1, 31.7Hz,...

Embodiment 3

[0020] Example 3 Inhibitory Effect of Modified Compound 15-1 on Strawberry Botrytis cinerea

[0021] ⑴Instruments and related materials

[0022] 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.

[0023] ⑵ medicine

[0024] The 93% phenazine-1-carboxamide modified 15-1 original drug prepared in Example 1 (hereinafter referred to as the modified 15-1); agar, glucose, acetone and Tween 80 were purchased from Sinopharm Group.

...

technical field

[0001] The invention belongs to the field of pesticide creation, and particularly relates to the application of phenazine-1-carboxamide modified compound 15-1 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.

[0003] 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 scle...

Examples

Embodiment 1

[0015] Example 1 Preparation of phenazine-1-carboxamide modified compound 15-1

[0016] The specific process of synthesis: hydrolyze phenazine-1-carboxamide under acidic conditions to generate phenazine-1-carboxylic acid; take 20mmol phenazine-1-carboxylic acid (0.4577g) and 200ml thionyl chloride and add it to a 500ml round bottom In the flask, a reflux reaction device (using anhydrous calcium chloride drying tube) was installed, magnetically stirred, and refluxed for 6 hours. After the reaction solution was cooled, the thionyl chloride was removed by rotary evaporation to obtain the intermediate product phenazine-1-formyl chloride. The purification is directly used in the next step reaction; the obtained phenazine-1-formyl chloride is dissolved in 200ml of dry dichloromethane (DCM), added to a 500ml dry round bottom flask, protected by nitrogen, magnetically stirred, and cooled in an ice-water bath 11.15ml of triethylamine (80mmol, 4equiv.) and 2.367g of 3-methoxy-1-propylam...

Embodiment 2

[0017] Example 2 Structural identification of modified compound 15-1

[0018] The modified compound 15-1 obtained was determined by proton nuclear magnetic resonance (1H NMR) and carbon nuclear magnetic resonance (13C NMR) techniques. Proton spectrum (1H NMR (500MHz, CDCl3) δ11.03 (s, 12H), 9.25–8.90 (m, 59H), 8.90–7.86 (m, 427H), 8.11–7.73 (m, 224H), 8.11–7.73 (m,223H),7.82(dd,J=16.5,10.4Hz,19H),7.29(s,16H),7.10–6.85(m,6H),5.86–5.75(m,8H),5.33–5.23(m ,9H),4.82(t,J=9.7Hz,9H),4.89–4.39(m,14H),4.89–4.24(m,19H),4.89–4.18(m,23H),4.89–4.07(m,29H ),4.89–4.02(m,32H),4.89–3.71(m,81H),3.68(d,J=20.8Hz,17H),3.71–3.51(m,22H),3.71–3.30(m,38H), 3.71–3.26(m,43H),3.71–3.20(m,53H),3.71–3.03(m,80H),3.71–3.05(m,80H),3.71–2.93(m,83H),3.71–2.88(m ,84H),3.71–2.81(m,85H),3.71–2.45(m,128H),3.71–2.41(m,133H),3.71–2.27(m,150H),3.71–2.17(m,155H),3.71 –2.12(m,159H),3.71–2.07(m,169H),3.71–2.01(m,175H),3.71–1.70(m,258H),3.71–1.62(m,273H),3.71–1.54(m, 292H), 3.71–1.40(m, 351H), 1.24(dd, J=37.1, 31.7Hz,...

Embodiment 3

[0020] Example 3 Inhibitory Effect of Modified Compound 15-1 on Strawberry Botrytis cinerea

[0021] ⑴Instruments and related materials

[0022] 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.

[0023] ⑵ medicine

[0024] The 93% phenazine-1-carboxamide modified 15-1 original drug prepared in Example 1 (hereinafter referred to as the modified 15-1); agar, glucose, acetone and Tween 80 were purchased from Sinopharm Group.

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