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Application of a class of 1,2,3-triazole-4-hydrazide derivatives in the preparation of agricultural fungicides
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A technology for hydrazide derivatives and agricultural fungicides is applied in the application field of a class of 1,2,3-triazole-4-hydrazide derivatives in the preparation of agricultural fungicides, and can solve agricultural production losses and plant diseases. Chemical control failure, etc.
Active Publication Date: 2017-05-24
NANJING AGRICULTURAL UNIVERSITY
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Until the 1970s, as modern fungicides with high efficiency, systemic absorption and strong selectivity were developed and widely used, fungicide resistance became more and more serious and common, which often led to the failure of chemical control of plant diseases and huge losses in agricultural production
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Embodiment 1
[0014] Example 1: Preparation of 1-(2-chlorophenyl)-N'-phenyl-1H-1,2,3-triazole-4-hydrazide (compound 1)
[0015]
[0016] Dissolve 1-(2-chlorophenyl)-1H-1,2,3-triazole-4-formyl chloride in an appropriate amount of dichloromethane solution, add phenylhydrazine (R=H), triethyl Amine, stirred at room temperature (20-30°C) for about 30 minutes, purified by silica gel column to obtain 1-(2-chlorophenyl)-N'-phenyl-1H-1,2,3-triazole-4- Hydrazide (1) is a red powder with a yield of 75%. m.p.216.3-216.5℃. 1 H-NMR (400MHz, DMSO-d 6 )δ10.61(s, 1H), 9.13(s, 1H), 8.01(s, 1H), 7.81(dd, J=11.3, 8.0Hz, 2H), 7.70(t, J=7.7Hz, 1H), 7.64(t, J=7.6Hz, 1H), 7.17(t, J=7.7Hz, 2H), 6.79(d, J=8.1Hz, 2H), 6.73(t, J=7.2Hz, 1H).ESI- MS: 314.08 (C 15 h 13 ClN 5 O[M+H] + ).
Embodiment 2
[0017] Example 2: Preparation of 1-(2-chlorophenyl)-N'-(2-fluorophenyl)-1H-1,2,3-triazole-4-hydrazide (compound 2)
[0018]
[0019] The preparation method is the same as in Example 1. Substitution of phenylhydrazine with 2-fluorophenylhydrazine affords 1-(2-chlorophenyl)-N'-(2-fluorophenyl)-1H-1,2,3-triazole-4-hydrazide (2) , as light yellow powder, yield 83%. m.p.99.9-102.7℃. 1 H-NMR (400MHz, DMSO-d 6 )δ10.66(s, 1H), 9.23(s, 1H), 9.14(s, 1H), 7.86-7.74(m, 2H), 7.69(d, J=1.5Hz, 2H), 7.16-7.06(m , 1H), 7.05-6.96(m, 1H), 6.88-6.79(m, 1H), 6.79-6.70(m, 1H).ESI-MS: 332.07(C 15 h 12 ClFN 5 O[M+H] + ).
Embodiment 3
[0020] Example 3: Preparation of 1-(2-chlorophenyl)-N'-(3-fluorophenyl)-1H-1,2,3-triazole-4-hydrazide (compound 3)
[0021]
[0022] The preparation method is the same as in Example 1. Substitution of phenylhydrazine with 3-fluorophenylhydrazine yields 1-(2-chlorophenyl)-N'-(3-fluorophenyl)-1H-1,2,3-triazole-4-hydrazide (3) , as a white powder with a yield of 77%. m.p.193.9-194.5℃. 1 H-NMR (400MHz, DMSO-d 6 )δ10.43(s, 1H), 8.61(s, 2H), 7.30(dd, J=15.0, 8.1Hz, 2H), 6.89-6.78(m, 4H), 6.74(td, J=8.7, 2.3Hz , 2H).ESI-MS: 332.07 (C 15 h 12 ClFN 5 O[M+H] + ).
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Abstract
The invention provides 1,2,3-triazole-4-hydrazide derivatives. The 1,2,3-triazole-4 hydrazide derivatives are characterized by comprising a general formula shown in the description, wherein, when R1 is equal to 2-Cl, R2 is equal to H, 2-F, 3-F, 4-F, 2-Cl, 3-Cl, 4-Cl, 2-Br, 2,5-2Cl, 2,6-2Cl, 3,5-2Cl, 2,5-2F or 2,3-2F; when R2 is equal to 2 or 3-2F, R1 is equal to H, 2-Cl, 3-Cl, 4-Cl, 2-F, 3-F, 4-F or 2,5-2Cl. The compounds, namely the 1,2,3-triazole-4 hydrazide derivatives, have relatively high inhibitory activity on plant pathogens, and can be used as an agricultural bactericide for plantdisease control.
Description
technical field [0001] The invention relates to the synthesis of a class of 1,2,3-triazole-4-hydrazide derivatives and their application as agricultural fungicides in plantdisease control. Background technique [0002] The use of fungicides to prevent and control plant diseases is one of the important measures to ensure high and stable crop yields. The fungicides used before the 1970s were almost all traditional protective fungicides, with many action sites, which were not easy to cause pathogenic bacteria to develop drug resistance. Until the 1970s, as modern fungicides with high efficiency, systemic absorption and strong selectivity were developed and widely used, fungicide resistance became more and more serious and common, which often led to the failure of chemical control of plant diseases and huge losses in agricultural production. (See: Qi Zhiqiu, Wang Jianxin, Chen Changjun, Zhou Mingguo. Research Progress on Resistance to Modern Fungicides [J]. Pesticides. 2006(10...
Claims
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