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Preparation and application of trifluoroacetyl anabasine compounds with insecticidal activity

A technology of compounds and compositions, applied in the fields of pesticides, organic chemistry, biocides, etc.

Inactive Publication Date: 2014-10-29
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, neonicotinoid insecticides have poor fat solubility and are difficult to penetrate into the waxy skin of insects, resulting in high efficiency against piercing-sucking pests and low activity against lepidopteran pests

Method used

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  • Preparation and application of trifluoroacetyl anabasine compounds with insecticidal activity
  • Preparation and application of trifluoroacetyl anabasine compounds with insecticidal activity
  • Preparation and application of trifluoroacetyl anabasine compounds with insecticidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The structural formula of some compounds of the present invention is one of the specific compounds listed in Table 1:

[0046] Table 1: Representative compounds represented by structural formula (A)

[0047]

[0048] Continuation

[0049]

[0050] Continuation

[0051]

Embodiment 2

[0052] Example 2. Preparation of the compound numbered 1 in embodiment 1

[0053]

[0054] Under ice-bath conditions, add 0.31 g (2.2 mmol) of (6-chloropyridin-3-yl)-methylamine, 0.45 g (2 mmol) of 4-chloro-1,1, 1,5,5,5-Hexafluoro-3-en-2-one, 0.3 mL (2.2 mmol) of triethylamine and 15 mL of dichloromethane, stirred reaction. The reaction was tracked by thin layer chromatography (TLC). When the reactant 4-chloro-1,1,1,5,5,5-hexafluoro-3-en-2-one disappeared, the reaction was stopped, and the crude product of the solvent was removed by rotary evaporation. Using dichloromethane and methanol as eluents for column chromatography separation, a light yellow powdery solid was obtained with a yield of 65%;

[0055] 1 H NMR (400 Mz, CDCl 3 ): δ 8.28 (d, J = 2.2 Hz, 1H, Py- H ), 7.51 (dd, J = 8.2 Hz, J = 2.4 Hz, 1H, Py- H ), 7.39 (d, J = 8.4 Hz, 1H, Py- H ), 6.01 (s, 1H), 4.62 (s, 2H, Py-C H 2 -), 4.10 (s, 1H).

Embodiment 3

[0056] Example 3. Preparation of the compound numbered 2 in embodiment 1

[0057]

[0058] Under ice-bath conditions, add 0.35 g (2.2 mmol) of N-((6-chloropyridin-3-yl)-methyl)methanamine, 0.45 g (2 mmol) of 4- Chloro-1,1,1,5,5,5-hexafluoro-3-en-2-one, 0.3 mL (2.2 mmol) of triethylamine and 15 mL of dichloromethane, stirred reaction. The reaction was tracked by thin layer chromatography (TLC). When the reactant 4-chloro-1,1,1,5,5,5-hexafluoro-3-en-2-one disappeared, the reaction was stopped, and the crude product of the solvent was removed by rotary evaporation. Using dichloromethane and methanol as eluents for column chromatography separation, a light yellow powdery solid was obtained with a yield of 82%;

[0059] 1 H NMR (400 Mz, CDCl 3 ): δ 8.27 (d, J = 2.0 Hz, 1H, Py- H ), 7.50 (dd, J = 8.4 Hz, J = 2.4 Hz, 1H, Py- H ), 7.37 (d, J = 8.4 Hz, 1H, Py- H ), 6.00 (s, 1H), 4.60 (s, 2H, Py-C H 2 -), 2.98 (s, 3H).

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Abstract

The invention aims to provide trifluoroacetyl anabasine compounds with obvious insecticidal activity, and a preparation method and application thereof. The invention particularly provides compounds disclosed as Formula (A), or cis-trans-isomers or pesticidally acceptable salts thereof. The invention also provides a preparation method of the compounds, or cis-trans-isomers or pesticidally acceptable salts thereof. The compounds has high insecticidal activity for Homoptera, Lepidoptera and other pests in agriculture and forestry, such as aphids, planthoppers, aleyrodids, leafhoppers, thrips, cotton bollworms, cabbage worms, cabbage moths, tobacco caterpillars, armyworms and the like.

Description

technical field [0001] The invention relates to the preparation and application of a neonicotinoid insecticide containing a trifluoroacetyl group pharmacophore. Background technique [0002] The discovery of neonicotinoid insecticides is considered to be a milestone in the development of agricultural chemistry in the past two decades. This class of insecticides can selectively act on the central nervous system of insects because their sites of action are nicotinic acetylcholine receptors (nAChRs). Nervous system, so it has the characteristics of high specificity, safety to non-target organisms such as mammals and birds, and no cross-resistance with traditional pesticides. Since the launch of imidacloprid by German Bayer in the early 1990s, six neonicotinoid insecticides, including nitenpyram, acetamiprid, thiamethoxam, thiacloprid, clothianidin, and dinotefuran, have been commercialized one after another. Registered in more than 120 countries, the annual global sales amount...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/61C07D277/32C07D405/12C07D239/30C07D307/14A01N43/40A01N43/54A01N43/78A01N43/08A01P7/04A01P5/00
CPCC07D213/61A01N43/08A01N43/40A01N43/54A01N43/78C07D239/30C07D277/32C07D307/14C07D405/12
Inventor 田忠贞李冬梅李秀珍
Owner UNIV OF JINAN
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