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Application of 3-acetylthiotetronic acid derivatives in fungicides for controlling plant pathogens

A technology of acetylthiotetraketonic acid and plant pathogenic bacteria, which is applied in the field of pesticides and achieves the effect of simple synthesis method

Active Publication Date: 2019-07-12
ANHUI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are few reports at home and abroad that the derivatives synthesized from 3-acetylthiotetratonic acid are used in the control of plant pathogens.

Method used

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  • Application of 3-acetylthiotetronic acid derivatives in fungicides for controlling plant pathogens
  • Application of 3-acetylthiotetronic acid derivatives in fungicides for controlling plant pathogens
  • Application of 3-acetylthiotetronic acid derivatives in fungicides for controlling plant pathogens

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Dissolve 158mg of 3-acetylthiotetraketonic acid in 50ml of toluene, add 271mg of benzaldehyde and 20mg of p-toluenesulfonic acid, heat and reflux for 10 hours, phenomenon: light yellow gradually disappears, cool to room temperature. The toluene solvent was evaporated by rotary evaporation, and the product was purified by using ethyl acetate and methanol as recrystallization solvents with a yield of 42%. Mp: 151-152°C. 1 H NMR (600MHz, DMSO-d 6 )δ: 7.81(s, 1H), 7.65(d, J=7.6Hz, 2H), 7.50(t, J=7.5Hz, 2H), 7.45(t, J=7.3Hz, 1H), 2.47(s, 3H), 13 C NMR (150MHz, DMSO-d 6 )δ: 195.85, 187.05, 186.03, 134.20, 131.13(2C), 130.90, 130.73, 129.67(2C), 127.31, 108.18, 26.68; MS[ESI]: m / z([M-H] - ),245.0643;

[0023]

[0024] 3-Acetyl-4-hydroxy-5-benzylidenethiophen-2(5H)-one was obtained.

Embodiment 2

[0026] Dissolve 158 mg of 3-acetylthiotetraketonic acid in 50 ml of toluene, add 290 mg of p-fluorobenzaldehyde and 20 mg of p-toluenesulfonic acid, heat and reflux for 10 hours, phenomenon: light yellow gradually disappears, and cool to room temperature. The toluene solvent was evaporated by rotary evaporation, and the product was purified by using ethyl acetate and methanol as recrystallization solvents with a yield of 53%. Mp: 181-183°C. 1 H NMR (600MHz, DMSO-d 6 )δ: 7.79(s, 1H), 7.71(dd, J=8.6, 5.6Hz, 2H), 7.35(t, J=8.8Hz, 2H), 2.46(s, 3H). 13 C NMR (150MHz, DMSO-d 6 )δ: 195.56, 186.86, 186.03, 164.02, 162.36, 133.46, 131.00, 129.35, 127.38, 116.89, 116.74, 107.98, 26.84; MS[ESI]: m / z([M-H] - ),263.0349;

[0027]

[0028] 3-Acetyl-4-hydroxy-5-(4-fluorobenzylidene)thiophen-2(5H)-one was obtained.

Embodiment 3

[0030] Dissolve 158 mg of 3-acetylthiotetraketonic acid in 50 ml of toluene, add 346 mg of p-trifluoromethylbenzaldehyde and 20 mg of p-toluenesulfonic acid, heat and reflux for 10 hours, phenomenon: light yellow gradually disappears, cool to room temperature . The toluene solvent was evaporated by rotary evaporation, and the product was purified by using ethyl acetate and methanol as recrystallization solvents with a yield of 55%. Mp: 162-164°C. 1 H NMR (600MHz, DMSO-d 6 )δ:7.84–7.79(m,4H),7.71(s,1H),2.40(s,3H). 13 C NMR (150MHz, DMSO-d 6 )δ: 193.76, 186.49, 186.01, 138.92, 132.80 131.08(2C), 126.27, 126.25(2C), 126.02, 109.98, 107.19, 27.54; MS[ESI]: m / z([M-H] - ), 314.0224;

[0031]

[0032] 3-Acetyl-4-hydroxy-5-(4-trifluoromethylbenzylidene)thiophen-2(5H)-one was obtained.

[0033] Three kinds of 3-acetylthiotetratonic acid derivatives 1-3 of the present invention are described as follows to the inhibition rate of apple rot fungus, corn leaf spot fungus, wheat hea...

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Abstract

The invention relates to application of 3-acetyl thiotetronic acid derivatives in bactericides for controlling phytopathogen. 3-acetyl thiotetronic acid is used as a raw material for synthesizing 3-acetyl-4-benzylidene thiotetronic acid, 3-acetyl-5-p-fluoro-benzylidene thiotetronic acid and 3-acetyl-5-p-trifluoromethyl benzylidene thiotetronic acid under different conditions. The bactericidal activities of the three compounds under different concentrations are measured and the corresponding EC50 values are computed. The 3-acetyl thiotetronic acid derivatives have superior activities in inhibiting bacteria of apple rot, leaf spot of corn, wheat scab and fusarium wilt of tomatoes, have the characteristics of easy degradation, low residual and the like as compared with traditional bactericides, have simple and economic synthetic methods, are lead compounds of bactericides of great value, and can be used for controlling apple rot, leaf spot of corn, wheat scab and fusarium wilt of tomatoes.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a synthesis method of 3-acetylthiotetronic acid derivatives and an application of the bactericidal activity thereof. Background technique [0002] Tetronic acid, whose parent structure is 4-hydroxy-5H-furan-2-one, widely exists in natural products, and has extensive and strong physiological activities on humans, animals or agricultural pests. It has become one of the hotspots in the research and development of new pesticides to use monomeric substances with excellent activity as template compounds to systematically modify or modify their structure and conduct structure-activity relationship (QSAR) research. 3-Acetylthiotetronic acid compounds have been reported due to their strong anti-tumor activity, and because the methylene group at the 5-position of 3-acetylthiotetronic acid is affected by the nearby electron-withdrawing group, it is easy to produce aldol Cond...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/32A01N43/10A01P3/00
CPCA01N43/10C07D333/32
Inventor 花日茂吕培陈议亮吴祥为
Owner ANHUI AGRICULTURAL UNIVERSITY
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