Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Fluorine-containing syn-form novel nicotine compound and preparation method and application thereof

A compound and composition technology, applied in the field of new neonicotinoid insecticides, can solve the problems of affecting the insecticidal activity of compounds, narrow insecticidal spectrum, and low activity of lepidopteran pests

Inactive Publication Date: 2015-04-29
UNIV OF JINAN
View PDF9 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, commercial neonicotinoid insecticides are highly effective against piercing-sucking pests, but have low activity against Lepidoptera pests, resulting in a narrow insecticidal spectrum
At the same time, the fat solubility of this type of insecticide is poor, and it is difficult to penetrate into the waxy skin of insects, which affects the insecticidal activity of this type of compound.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Fluorine-containing syn-form novel nicotine compound and preparation method and application thereof
  • Fluorine-containing syn-form novel nicotine compound and preparation method and application thereof
  • Fluorine-containing syn-form novel nicotine compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0012] The preparation method of the compound of the present invention

[0013] The compounds of the present invention can be synthesized by the reaction steps described above. Those skilled in the art can synthesize intermediates in the reaction steps according to prior art documents;

[0014] The preparation method of the compound of the present invention can be the preparation method commonly used in this field, and the present invention provides a kind of preferred preparation method of the compound described in general formula (A), comprises method:

[0015] Under solvent-free conditions, the compound of formula (b), the compound of formula (c) and the compound of formula (d) are reacted to obtain the compound of formula (A):

[0016]

[0017] In the above formulas, R 1 , R 2 as defined in claim 1;

[0018] In a preferred example, the reaction temperature is 100-150°C, preferably 110-130°C.

[0019] Insecticidal activity of the active substance of the present ...

Embodiment 1

[0025] The compound synthesis in the embodiment is carried out according to the following steps:

[0026]

[0027] Add 5 mmol 2-chloro-5-(2-nitromethylene-imidazolidin-1-ylmethyl)-pyridine, 5 mL triethyl orthoformate, 6 mmol ethyl trifluoroacetoacetate aniline derivative into a 50 mL round bottom In the flask, reflux and stir for 3 hours. After cooling, filter with suction and wash with petroleum ether. The resulting solid product was separated by column chromatography (dichloromethane:methanol=10:1) to obtain a yellow powdery solid;

[0028] Compound experimental data:

[0029] Compound 1

[0030] Yield: 70%. Melting point: 184-185°C. 1 H NMR (CDCl 3 )δ(ppm): 8.58(s, 1H), 8.34(d, 1H, J=1.6Hz, Py-H), 8.11(s, 1H), 7.80(dd, 1H, J 1 =2.0Hz,J 2 =8.0Hz, Py-H), 7.54(s, 1H, Py-H), 7.53(s, 1H, Ph-H), 7.35(m, 3H, Ph-H), 7.17(t, 1H, J= 7.2Hz, Ph-H), 5.09(d, 1H, J=15.2Hz, Py-CH 2 ), 4.42 (d, 1H, J=15.6Hz, Py-CH 2 ), 4.21-3.63 (m, 4H, N-CH 2 -CH 2 -N).IR(KBr,cm -1 ): 3274...

Embodiment 2

[0061] Embodiment 2. The insecticidal activity test of compound of the present invention

[0062] Insecticidal activity against planthoppers

[0063] Planthoppers are homoptera pests with piercing and sucking mouthparts, and are a common crop pest. The brown planthopper (Nilaparvata lugens) was used as the test object, and the spray method was used to test;

[0064] Operation process: the compound to be tested is accurately prepared into a 500, 250 ppm solution with acetone as a solvent, and treated with acetone aqueous solution as a blank control. Each treatment was replicated 3 cups (ie replicated 3 times). Spray 2ml per cup evenly with a small manual sprayer. 6 hours before spraying, 10 rice planthoppers were inoculated in each pot. A total of 3 batches of tests were carried out. After 24 hours of treatment, the number of dead insects of the test insects was counted, and the mortality rate (%) was calculated. The results are shown in Table 1;

[0065] Mortality rate ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a fluorine-containing syn-form novel nicotine compound and a preparation method and application thereof, particularly provides a compound adopting a structure shown in formula (A) or acceptable salt in agricultural pharmacology of the compound, and a preparation method and application of the compound, and further relates to an agricultural composition comprising the compound or the acceptable salt in agricultural pharmacology and application of the composition. The compound has high insecticidal activity towards homoptera agricultural and forestry pests, such as plant hopper and whitefly.

Description

technical field [0001] The invention relates to a novel neonicotinoid insecticide, a preparation method and application thereof. Background technique [0002] Neonicotinoid insecticides are considered as the fourth generation of insecticides and are the classic representatives of green insecticides. It has an irreplaceable position in the field of chemical pesticides. This kind of insecticide acts on the insect nicotinic acetylcholine receptor, is a potent agonist of the receptor, and is highly selective. Its high efficiency, low toxicity, and environmental friendliness are currently hot areas of pesticide creation. Since Bayer in Germany launched imidacloprid in the early 1990s, major pesticide companies have successively launched 6 neonicotinoid insecticides. This type of insecticide is currently the most important chemical insecticide and has been used in more than 120 countries. Registered, annual global sales of more than 2.5 billion US dollars, market share of more ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D471/04A01N43/90A01P7/04
CPCA01N43/90C07D471/04
Inventor 田忠贞李冬梅崔书霞
Owner UNIV OF JINAN
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com