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A class of chloroisothiazole neonicotinoid compounds and their preparation method and use

A neonicotinoid and isothiazole technology, applied in the field of chloroisothiazole neonicotinoid heterocyclic compounds, can solve unscientific and reasonable problems

Inactive Publication Date: 2018-08-17
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to a large number of unscientific and rational use for a long time, the current pests have developed resistance to this kind of insecticides

Method used

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  • A class of chloroisothiazole neonicotinoid compounds and their preparation method and use
  • A class of chloroisothiazole neonicotinoid compounds and their preparation method and use
  • A class of chloroisothiazole neonicotinoid compounds and their preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of chloroisothiazole neonicotinoid compound I:

[0030] Into a 100 ml round bottom flask were added successively 3,4-dichloro-5-chloromethylisothiazole (0.3 g, 1.45 mmol), the anonicotinoid intermediate R 2-H (2.03 mmol), potassium carbonate (0.28 g, 2.03 mmol), potassium iodide (33.2 mg, 0.20 mmol) and the phase transfer catalyst tetrabutylammonium bromide (TBAB) (32.2 mg, 0.10 mmol), Then add 30 milliliters of acetonitrile solution, finally add 1 milliliter of N,N-dimethylformamide (DMF), stir and reflux at 80 degrees Celsius for 3 to 5 hours, TLC detects the reaction, after the reaction is completed, remove the insolubles by filtration, the filtrate Concentrate under reduced pressure, add ethyl acetate to the residue, wash once with saturated sodium bicarbonate solution and saturated sodium chloride solution respectively, keep the organic phase, back-extract the aqueous phase with ethyl acetate twice, combine the organic phases, Dry over magnesium sulfat...

Embodiment 2

[0032] The antibacterial activity assay result of chloroisothiazole neonicotinoid compound I of the present invention:

[0033] The codes and titles of common plant pathogenic fungi tested in the present invention are as follows: AS: tomato early blight fungus, its Latin name is: Alternaria solani, BC: cucumber cinerea, its Latin name is: Botrytis cinerea, CA: peanut brown spot fungus , its Latin name: Cercospora arachidicola, GZ: wheat scab, its Latin name: Gibberella zeae, PI: potato infestans, its Latin name: Phytophthora infestans (Mont.) deBary, PP: apple ringworm , its Latin name is: Physalospora piricola, PS: Rice sheath blight, its Latin name is: Pellicularia sasakii, RC: Rhizoctonia graminearum, its Latin name is: Rhizoctonia cerealis, SS: Sclerotinia sclerotiorum, its Latin name Named: Sclerotinia sclerotiorum, these strains are well represented and can represent the species of most pathogenic bacteria that occur in the field in agricultural production.

[0034] Com...

Embodiment 3

[0037] Chlorinated isothiazole neonicotinoid compound I insecticidal activity of the present invention:

[0038] The insecticidal activity assay result of chloroisothiazole neonicotinoid compound I is shown in Table 4, and it can be seen in table 4: most of chloroisothiazole neonicotinoid compound I of the present invention have better insecticidal activity, and in the test When the concentration of the agent is 100 mg / L, after 72 hours of observation, the chloroisothiazole neonicotinoid compound I of the present invention has a good poisoning effect on aphids, and the insecticidal activity of the compound zgn07-40-1 is 92.23 %, 51.83% higher than that of imidacloprid, the commercial species closest to its chemical structure, and more than 40%; the insecticidal activity of compound zgn08-4 was 57.32%, 39.88% higher than that of thiamethoxam, its closest commercial species % is more than 10%; the inhibitory activity of compound zgn09-114 is 50.55%, which is more than 20% higher...

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PUM

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Abstract

The invention provides a chloroisothiazole neonicotine compound, as well as a preparation method and application thereof. The 3,4-dichloroisothiazole neonicotine compound has a chemical structural general formula as shown in a formula I. The formula is as shown in the specification. The invention further discloses a structure general formula, a synthesizing method of the compound, application of the compound as insecticides, bactericides and plant virucides, application of a composition of the compound, agriculturally acceptable auxiliary or synergist and commercial insecticide, bactericide, plant virucdies and acaricides in prevention and control of insect pests, diseases and virus diseases of agricultural, forestal and horticultural plants and a preparation method of the composition.

Description

technical field [0001] The technical scheme of the invention relates to N- and S-containing chloroisothiazole neonicotinoid heterocyclic compounds, in particular to 3,4-dichloroisothiazole-containing neonicotinoid heterocyclic compounds. Background technique [0002] Five-membered aromatic heterocyclic compounds are an important source of pesticide precursors, and the commercialized pesticides include the insecticide clothianidin and the fungicide benthiazil, etc. The research and development of isothiazole is relatively lagging behind. Isotianil can stimulate the natural defense mechanism of rice to prevent and control rice blast (Assmann et al., WO 9924413, 1999), and is a typical plant activator; this type of agent does not directly act on target organisms such as pests and diseases, but acts on plant Its own defense system enables plants to gain defense against subsequent diseases, which belongs to "green pesticides". The synthesis method and biological activity of Iso...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06C07D275/02A01N43/80A01N43/88A01P1/00A01P3/00A01P7/02A01P7/04
CPCA01N43/80A01N43/88C07D275/02C07D417/06
Inventor 范志金宗广宁马刘勇张乃楼郭晓凤朱玉洁陈来钱晓琳王海霞张秩鸣梁福起田海丰
Owner NANKAI UNIV
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