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Triazine heterocyclic compound with nematicidal activity as well as preparation method and application of triazine heterocyclic compound

A compound and heterocyclic group technology, applied in the field of triazine heterocyclic compounds, can solve problems such as pollution, increased difficulty in nematode control, and low safety

Active Publication Date: 2015-04-22
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Widely used chemical nematocides are mainly highly toxic and high residual organophosphorus or carbamate pesticides, such as thifamifos, profenamiphos, fenamiphos, thiazophos, aldicarb, fenamicarb and carbamate It has low safety to humans and other non-target organisms, and it will also cause varying degrees of pollution to soil, water sources and agricultural products.
In addition, due to the single variety, the excessive and frequent use of this type of nematicides has caused serious drug resistance, making the control of nematodes increasingly difficult

Method used

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  • Triazine heterocyclic compound with nematicidal activity as well as preparation method and application of triazine heterocyclic compound
  • Triazine heterocyclic compound with nematicidal activity as well as preparation method and application of triazine heterocyclic compound
  • Triazine heterocyclic compound with nematicidal activity as well as preparation method and application of triazine heterocyclic compound

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Experimental program
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preparation example Construction

[0111] The preparation method of the compound of the present invention

[0112] The compound represented by the general formula (I) of the present invention can be prepared by the following method, but the conditions of the method, such as the amount of reactant, solvent, base, compound used, reaction temperature, reaction time required, etc. are not limited to the following explanations . The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in the specification or known in the art. Such a combination can be easily performed by those skilled in the art to which the present invention belongs.

[0113] In the preparation method of the present invention, each reaction is usually carried out in an inert solvent at a reaction temperature of -20-120°C (preferably -10-0°C or 20-30°C or 80-100°C). The reaction time is usually 2 to 24 hours, preferably 4 to 18 hours.

[0114] The base used in the reaction ...

Embodiment 1

[0155] Example 12-cyanoimino-3-(N-3-(4-oxo-7-chlorobenzo[d][1,2,3]triazin-3(4H)-yl)propyl)) -1,3-Thiazolidin-4-one

[0156] 1.1 Preparation of 7-chlorobenzo[d][1,2,3]triazin-4(3H)-one

[0157] 1.1.1 Preparation of 7-chloroisatoic anhydride

[0158]

[0159] Add 6.864g (40mmol) of 2-amino-4-chlorobenzoic acid into 100ml of tetrahydrofuran, stir it to form a suspension, lower it to -10°C, control the temperature at -10~-5°C, and slowly add 11.88g (40mmol ) BTC in 20ml tetrahydrofuran solution, after the addition was completed, it was placed at room temperature for reaction, and TLC followed the reaction process. After the reaction, the solvent was evaporated under reduced pressure, 150ml of anhydrous diethyl ether was added to the residual solid, stirred thoroughly, suction filtered, the filter cake was washed with anhydrous diethyl ether, and dried to obtain 6.718g of white solid, with a yield of 85%. 1 HNMR (400MHz, DMSO-d 6 )δ11.84(s,1H),7.92(d,J=8.4Hz,1H),7.30(dd,J 1...

Embodiment 2

[0175] Example 22-cyanoimino-3-(N-(4-(4-oxo-7-fluorobenzo[d][1,2,3]triazin-3(4H)-yl)butyl) )-1,3-thiazolidin-4-one

[0176]

[0177] The synthesis of the target compound is similar to step 1.4 of Example 1, except that 3-(4-bromobutyl)-7-fluorobenzo[d][1,2,3]triazine-4(3H) -one instead of 3-(3-bromopropyl)-7-chlorobenzo[d][1,2,3]triazin-4(3H)-one. Yellow solid, yield 53%. 1 HNMR (400MHz, DMSO-d 6 )δ8.33(dd,J 1 =8.8Hz,J 2 =5.6Hz,1H),8.07(dd,J 1 =8.8Hz,J 2 =2.4Hz,1H),7.81(td,J 1 =8.8Hz,J 2 =2.4Hz, 1H), 4.39(t, J=6.8Hz, 2H), 4.31(s, 2H), 3.65(t, J=6.8Hz, 2H), 1.90-1.75(m, 2H), 1.69-1.56 (m,2H); 19 FNMR (376MHz, DMSO-d 6 )δ-101.9(td,J 1 =8.6Hz,J 2 =5.6Hz).HRMS(ES-)C 15 h 12 N 6 o 2 FS(M-H) – , calculated value: 359.0726, measured value: 359.0723.

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Abstract

The invention relates to a triazine heterocyclic compound with nematicidal activity as well as a preparation method and application of the triazine heterocyclic compound and particularly discloses a compound as shown in the formula (I) or an optical isomer, cis-trans isomer or pesticidally-acceptable salt of the compound and a preparation method of the compound or the optical isomer, cis-trans isomer or pesticidally-acceptable salt of the compound. The invention also discloses an agricultural composition containing the compound and application of the agricultural composition. The compound has excellent nematicidal activity.

Description

technical field [0001] The invention belongs to the field of pesticides. Specifically, the present invention relates to a triazine heterocyclic compound with nematicide activity, its preparation method and application. Background technique [0002] Plant parasitic nematodes are a class of pathogenic microorganisms that are extremely harmful. They have a wide range of distribution, a wide variety, and strong environmental adaptability. They can parasitize in the roots, stems, leaves, seeds, sprouts, and fruits of plants. It causes mechanical damage to the host plant and plunders the host plant's nutrition, especially its esophageal gland secretion will cause a series of pathological changes in the host plant, and it will also infect the host plant together with other pathogenic microorganisms, causing compound diseases and resulting in yield loss. Globally, plant parasitic nematodes cause agricultural losses of more than 100 billion U.S. dollars every year, seriously restric...

Claims

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Application Information

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IPC IPC(8): C07D417/06C07D491/113C07D403/06C07D417/12C07D413/12C07D253/08C07D495/04A01N47/40A01N43/707A01N43/824A01N43/76A01N43/828A01N47/36A01N47/28A01P5/00
CPCA01N43/707A01N43/76A01N43/82A01N43/88A01N43/90A01N47/34A01N47/36C07D253/08C07D403/06C07D413/12C07D417/06C07D417/12C07D471/04C07D491/113C07D495/04A01N2300/00A01N47/40
Inventor 徐晓勇李忠王高磊陈修雷张经纬邵旭升须志平周珍陈琦张梦婷王容义
Owner EAST CHINA UNIV OF SCI & TECH
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