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Dithiolane-containing cis-anabasine 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 severe resistance, narrow insecticidal spectrum, and limited selectivity of insect pest control drugs

Inactive Publication Date: 2014-06-18
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the large and frequent use of neonicotinoid insecticides has caused serious resistance problems, which limits the application of this type of compound to a certain extent; at the same time, the toxicity of this type of compound to bees has increasingly attracted people's attention and has become a constraint. Important issues in the development of such compounds
Moreover, neonicotinoid insecticides are mainly effective against Homoptera and Coleoptera pests, and their relatively narrow insecticidal spectrum also limits the selectivity of insecticides in pest control.

Method used

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  • Dithiolane-containing cis-anabasine compound and preparation method and application thereof
  • Dithiolane-containing cis-anabasine compound and preparation method and application thereof
  • Dithiolane-containing cis-anabasine compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1. Synthesis of compound 1

[0051]

[0052] 2-Chloro-5-(2-nitromethylene-imidazolidin-1-ylmethyl)-pyridine (5 mmol), 4-amino-1,2-dithiolane (5.5 mmol), 37 % formaldehyde solution (11 mmol) was added to a 50 mL round bottom flask, and stirred overnight at room temperature. Filter with suction and spin dry the solvent to obtain the crude product. Further separation by column chromatography (dichloromethane: methanol = 10:1) gave a light yellow powdery solid with a yield of about 63%. 1 H NMR (400 Mz, CDCl 3 ): δ 8.26 (d, J = 2.2 Hz, 1H), 7.54 (dd, J = 8.0 Hz, J = 2.2 Hz , 1H), 7.36 (d, J = 8.1 Hz, 1H), 4.90 (d, J = 15.0 Hz, 1H), 4.53 (d, J = 15.0 Hz, 1H), 3.72-3.92 (m, 4H), 3.68 (s, 4H), 2.92 (m, 1H), 2.56-2.75 (m, 4H); HRMS(ES+) calculated value C 15 h 19 N 5 o 2 S 2 35 Cl(M+H)+, 400.0669; Found, 400.0661.

[0053]

Embodiment 2

[0054] Example 2. Synthesis of compound 2

[0055]

[0056] 1-((2-chlorothiazol-5-yl)methyl)-2-(nitromethylene)-1-imidazolidine (5 mmol), 4-amino-1,2-dithiolane (5.5 mmol), 37% formaldehyde aqueous solution (11 mmol) were added into a 50 mL round bottom flask, and stirred overnight at room temperature. Filter with suction and spin dry the solvent to obtain the crude product. Further separation by column chromatography (dichloromethane: methanol = 10:1) gave a light yellow powdery solid with a yield of about 52%. 1 H NMR (400 Mz, CDCl 3 ): δ 6.72 (s, 1H), 4.83 (d, J = 15.0 Hz, 1H), 4.38 (d, J = 15.0 Hz, 1H), 3.65-3.83 (m, 4H), 3.61 (s, 4H), 2.90 (m, 1H), 2.48-2.72 (m, 4H); HRMS(ES+) calculated value C 13 h 17 N 5 o 2 S 3 35 Cl(M+H)+, 406.0233; Found, 406.0237.

[0057]

Embodiment 3

[0058] Example 3. Synthesis of compound 3

[0059]

[0060] Nitenpyram (5 mmol), 4-amino-1,2-dithiolane (5.5 mmol), and 37% aqueous formaldehyde (11 mmol) were added into a 50 mL round bottom flask, and stirred overnight at room temperature. Filter with suction and spin dry the solvent to obtain the crude product. Further separation by column chromatography (dichloromethane: methanol = 10:1) gave a light yellow powdery solid with a yield of about 32%. 1 H NMR (400 Mz, CDCl 3 ): δ 8.32 (d, J = 2.2 Hz, 1H), 7.72 (dd, J = 8.0 Hz, J = 2.2 Hz , 1H), 7.34 (d, J = 8.1 Hz, 1H), 4.50 (d, J = 15.0 Hz, 1H), 4.41 (d, J = 15.0 Hz, 1H), 3.68-3.89 (m, 4H), 3.70 (s, 4H), 2.88 (m, 1H), 2.46-2.73 (m, 4H); HRMS(ES+) calculated value C 16 h 23 N 5 o 2 S 2 35 Cl(M+H)+, 416.0982; Found, 416.0978.

[0061]

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Abstract

The invention relates to a dithiolane-containing cis-anabasine compound and a preparation method and application thereof, in particular provides a compound with a structure shown in type (A) or a pesticide-pharmaceutically acceptable salt of the compound, and a preparation method and application thereof, and also relates to an agricultural composition comprising the compound or the pesticide-pharmaceutically acceptable salt of the compound, and application thereof. The compound has a high insecticidal activity to homoptera, lepidoptera and other agricultural and forestry pests such as aphids, whitefly, planthoppers and the like.

Description

[0001] Technical field [0002] The invention involves new types of pesticides, and its preparation methods and applications. [0003] Background technique [0004] The fourth -generation pesticides after the newbine pesticides are considered to be an insecticide after organic phosphorus, amino amino acid ester, and pest division, and have an irreplaceable position in the field of chemical pesticides.Pepacin is the first nicotin pesticide developed by Bayer. Since this type of pesticide has a unique mechanism and does not interact with conventional insecticides, it not only has efficient, broad -spectrum and good root rootsInternal absorption, touch and gastric toxicity, and low toxicity to mammals, safe environment.It can effectively prevent pests such as the same wings, cypling eyes, winged eyes, and bulb -winged eyes.Since then, major pesticide companies have successively launched their own new nicotin pesticides. This type of pesticide is already the most important pesticide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D409/14A01N43/90A01N43/54A01P7/04
CPCA01N43/54A01N43/90C07D409/14C07D487/04
Inventor 田忠贞李冬梅崔书霞
Owner UNIV OF JINAN
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