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Hydrazone-containing triazolinone compounds and uses thereof

A compound and selected technology are applied in the field of agricultural fungicides and insecticides, and can solve problems such as compounds that have not been reported

Active Publication Date: 2013-03-27
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In the prior art, the compound shown in the general formula of the present invention has not been reported

Method used

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  • Hydrazone-containing triazolinone compounds and uses thereof
  • Hydrazone-containing triazolinone compounds and uses thereof
  • Hydrazone-containing triazolinone compounds and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0136] Embodiment 1: the preparation of compound 1

[0137]

[0138] 1) Preparation of 4-amino-3-methyl-1H-1,2,4-triazol-5(4H)-one

[0139] In a 250-milliliter three-neck bottle equipped with a thermometer and a water separator, add 11.7 grams of phenol, 11.1 grams of urethane and 12.5 grams of hydrazine hydrate (85%) in sequence, heat to 110-120 ° C, and dropwise add 4.2 grams of ammonia ( 25%), the water separator divides the water. After reacting for 6 hours, the temperature rose to 180°C, and low boiling point substances were gradually separated. The next day, the temperature was raised to 80°C, 5 grams of hydrazine hydrate (85%) and 25 grams of acetonitrile were added dropwise, the temperature was raised to 140°C, and the reaction was carried out for 7 hours. After cooling, a solid precipitated out, suction filtered, and washed 2-3 times with petroleum ether to obtain light yellow needles. The solid was 38 g, which was directly used in the next reaction without furth...

Embodiment 2

[0145] Embodiment 2: the preparation of compound 11

[0146]

[0147] 1) Preparation of (E)-3-methyl-4-(benzylimino)-1H-1,2,4-triazol-5(4H)-one

[0148] The synthesis process was according to step 2) in Example 1, and 14.7 grams of 2-thiophenecarbaldehyde was replaced by 13.9 grams of benzaldehyde to obtain 20.6 grams of light yellow solid.

[0149] 2) Preparation of compound 11

[0150] The synthesis process is according to step 3) in example 1, 0.5 gram (E)-3-methyl-4-(thiophene-2-methylimino)-1H-1,2,4-triazole-5(4H) The -ketone was replaced by 0.49 g of (E)-3-methyl-4-(benzylimino)-1H-1,2,4-triazol-5(4H)-one to obtain 0.50 g of a white solid. Melting point: 62-64°C.

[0151]1 HNMR (CDCl 3 , 300MHz) δ (ppm): 9.82 (s, 1H), 7.79 (m, 1H), 7.45 (m, 4H), 6.08 (t, 1H), 4.53 (d, 2H), 2.39 (s, 3H).

Embodiment 3

[0152] Embodiment 3: the preparation of compound 14

[0153]

[0154] 1) Preparation of (E)-3-methyl-4-(4-chlorobenzylimino)-1H-1,2,4-triazol-5(4H)-one

[0155] The synthesis process was carried out according to step 2) in Example 1, and 14.7 grams of 2-thiophenecarbaldehyde was replaced by 18.4 grams of p-chlorobenzaldehyde to obtain 21.5 grams of light yellow solid.

[0156] 2) Preparation of Compound 14

[0157] The synthesis process is according to step 3) in example 1, 0.5 gram (E)-3-methyl-4-(thiophene-2-methylimino)-1H-1,2,4-triazole-5(4H) -Kone was replaced by 0.56 g of (E)-3-methyl-4-(4-chlorobenzyl imino)-1H-1,2,4-triazole-5(4H)-one to give 0.53 g of white solid . Melting point: 96-98°C.

[0158] 1 HNMR (CDCl 3 , 300MHz) δ (ppm): 9.82 (s, 1H), 7.72 (d, 2H), 7.42 (d, 2H), 6.08 (t, 1H), 4.53 (d, 2H), 2.39 (s, 3H).

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Abstract

The present invention discloses hydrazone-containing triazolinone compounds, which have a structure represented by a general formula I, wherein various substituents are defined in an instruction. The compounds represented by the general formula I can be used for prevention and control of plant diseases and insect pests in agricultural fields, wherein the compounds have high biological activity, such that good effects can be obtained with the low dose compounds. Accordingly the present invention discloses uses of the compounds represented by the general formula I as sterilization agents and insecticide in agriculture and other fields.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides and insecticides. Specifically, it relates to a hydrazone-containing triazolinone compound and its application. Background technique [0002] The triazolinone compounds containing hydrazone have good bactericidal, insecticidal and herbicidal activities. Patent WO9518123 relates to the following compounds as insecticides: [0003] [0004] Compound A [0005] Patent GB2194534 involves the following compounds as herbicides: [0006] [0007] Compound B [0008] Patent US3260588 involves the following compounds as bactericides and insecticides: [0009] [0010] Although there are many patents, there is still a need to continuously develop new compounds to control diseases, insects, and weeds in agriculture. Although all the compounds disclosed in the above-mentioned patents have certain similarities with the compounds of the present invention, there are still significant differe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/12C07D249/14C07D403/12C07D413/14C07D401/12A01N43/653A01N43/76A01N43/836A01P3/00A01P7/02A01P7/04
Inventor 杨吉春吴峤单中刚姜美峰梁博李志念王军锋刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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