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Nitrogen heterocyclic ring dichlorin allyl ether compounds with insecticidal activity

A technology of dichloroallyl ether and insecticidal activity, applied in the directions of biocides, chemicals for biological control, biocides, etc., to achieve the effect of high biological activity and good effect

Active Publication Date: 2009-01-07
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many pest control agents on the market, there is still a need for new compounds that are more efficient, safe, economical, and have different modes of action

Method used

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  • Nitrogen heterocyclic ring dichlorin allyl ether compounds with insecticidal activity
  • Nitrogen heterocyclic ring dichlorin allyl ether compounds with insecticidal activity
  • Nitrogen heterocyclic ring dichlorin allyl ether compounds with insecticidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] This example illustrates the preparation of compound 01 in Table 1.

[0090]

[0091] Step A: Synthesis of 2-methoxy-4-hydroxy-6-trifluoromethylpyrimidine (01-A)

[0092] Add 1.00 g of cyanamide into a 100 ml three-necked flask with a dry condenser, and add 5.00 g of HCl in methanol while stirring. Slowly raise the temperature to 25-80°C and react for 2-6 hours, cool in an ice-water bath to about 10°C, and then add 3.50 g of ethyl trifluoroacetoacetate dropwise. After the addition, adjust the pH value to 14 with 20% NaOH solution. Control the temperature below 30°C, raise the temperature to reflux after the addition, react for 5 to 6 hours, and desolvate under reduced pressure, add 20 grams of water to adjust the pH to be acidic, until the amount of precipitated solids is the largest, and dry to obtain about 3.0 g of the crude product. Content 96% (HPLC).

[0093] Step B: Synthesis of 2-methoxy-4-chloro-6-trifluoromethylpyrimidine (01-B)

[0094] Add 3.88g (20mmol...

Embodiment 2

[0106] This example illustrates the preparation of compound 06 in Table 1.

[0107]

[0108] Step A: Synthesis of 4-(3-bromopropoxy)-2-ethoxy-6-methylpyrimidine (06-A)

[0109] Synthesize with reference to the corresponding method in Example 1.

[0110] Step B: 4-(3-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)propoxy-2-ethoxy-6-methylpyrimidine ( 06) Synthesis

[0111] In a 100ml three-necked flask equipped with a dry condenser, add 2.6g (06-A), 2.7g (01-F), 1.3g potassium carbonate and 20ml DMF, react at room temperature for 10-20 hours, pour into water, wash with water, and acetic acid Extracted with ethyl ester, dried over anhydrous sodium sulfate, and removed the solvent under reduced pressure to obtain 5.4 g of yellow liquid, content 42% (HPLC), yield 51%, through column chromatography (petroleum ether: ethyl acetate = 100:1) After purification, the title compound (06) was obtained as a yellow sticky solid, the structure of which was confirmed by mass spectrometry...

Embodiment 3

[0113] This example illustrates the preparation of compound 08 in Table 1.

[0114]

[0115] Step A: Synthesis of 4-(3-bromopropoxy)-2-methylthio-6-trifluoromethylpyrimidine (08-B)

[0116] In a 100ml three-neck flask equipped with a dry condenser, add 3.5g 2-methylthio-4-chloro-6-trifluoromethylpyrimidine, 2.75g 3-bromopropanol, 2.75g potassium carbonate and 20mlDMF, and react at room temperature for 8 hours, the reaction was completed, poured into water, washed with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 5.08 g of the title compound as a yellow liquid with a content of 86% (HPLC).

[0117] Step B: 4-(3-(2,6-Dichloro-4-(3,3-dichloroallyloxy)phenoxy)propoxy-2-methylthio-6-(trifluoromethyl base) synthesis of pyrimidine (08)

[0118] Add 50ml of DMF, 3.3g 2-methylthio-4-(3-bromopropoxy)-6-trifluoromethylpyrimidine, 3.4g 4-(3 , 3-dichloropropenyloxy) phenol, 3.4g of anhydrous pot...

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Abstract

The invention discloses a nitrogen heterocyclic ring dichloro-allyl ether compound which is shown in a formula (1) and has the insecticidal activity, and a preparation method thereof, wherein, R, n, A, and B are limited, as shown in an instruction book.

Description

technical field [0001] The present invention relates to certain nitrogen-containing heterocyclic dichloroallyl ether compounds with insecticidal biological activity and compositions thereof, methods for using them to control pests in agricultural and non-agricultural environments, and their preparation methods. Background technique [0002] Pest control is very important in achieving efficient agriculture. Also pest control is important in forestry, greenhouse crops, ornamental plants, nursery crops, stored food and fiber products, livestock, household, and public health and animal care. Although there are many pest control agents on the market, there is still a need for new compounds that are more efficient, safe, economical and have different modes of action. [0003] Japan's Sumitomo Corporation disclosed a dichloropropene compound i with insecticidal activity in JP 09194418, US 5922880, and found the new Pyridalyl insecticide shown in formula ii, and its trade name is S...

Claims

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Application Information

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IPC IPC(8): C07D239/52C07D239/56C07D213/63C07D215/227A01N43/54A01N43/42A01N43/40A01P7/00
Inventor 柳爱平刘兴平黄路裴晖黄明智胡志彬任叶果胡礼喻快刘伟
Owner HUNAN CHEM RES INST
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