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Benzyloxypyrimidine derivative, agricultural/horticultural insecticide comprising derivative and method for using same

A technology of benzyloxypyrimidine and derivatives, applied in the field of agricultural and horticultural pesticides, can solve problems such as undisclosed

Inactive Publication Date: 2013-10-02
NIHON NOHYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the pyrimidine derivatives described in Patent Document 2 are disclosed to be useful as insecticides, compounds having the substituent disclosed in the present invention at the 4-position of pyrimidine are not disclosed

Method used

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  • Benzyloxypyrimidine derivative, agricultural/horticultural insecticide comprising derivative and method for using same
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  • Benzyloxypyrimidine derivative, agricultural/horticultural insecticide comprising derivative and method for using same

Examples

Experimental program
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Embodiment 1

[0481] Preparation of 4-(4-tert-butylbenzyloxy)-5-methoxypyrimidine (Compound No. 1-1)

[0482]

[0483] At 0°C, add 4-chloro-5-methoxypyrimidine (1.5 g, 10.3 mmol) and 4-tert-butylbenzyl alcohol (2.55 g, 15.6 mmol) described in Journal of the Chemical Society (1960), 4590 ) in dimethylacetamide (10 mL) was added sodium hydride (0.625 g, 15.6 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(4-tert-butylbenzyloxy)-5-methoxypyrimidine (2.16 g).

[0484] Yield: 77%

[0485] Properties: Melting point 58-59℃.

Embodiment 2

[0487] Preparation of 4-(4-trifluoromethylbenzyloxy)-5-phenoxypyrimidine (Compound No. 1-95)

[0488]

[0489] 4-Chloro-5-phenoxypyrimidine (0.4 g, 1.9 mmol) and 4-trifluoromethylbenzyl alcohol (0.36 g, 2.0 mmol) described in JP-A-49-92080 were dissolved in di To a solution in methylacetamide (7 m) was added sodium hydride (0.093 g, 2.3 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 4-(4-trifluoromethylbenzyloxy)-5-phenoxypyrimidine (0.60 g).

[0490] Yield: 85%

[0491] Melting point: 56-57°C.

[0492]Typical formulation examples and experimental examples of the present invention are shown below, but they should not be construed as limiting the scope of the present invention.

[049...

preparation Embodiment 1

[0495] Compound of the present invention 10 parts

[0496] Xylene 70 parts

[0497] 10 parts of N-methylpyrrolidone

[0498] Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts

[0499] An emulsifiable cream is prepared by mixing the above ingredients well to achieve dissolution.

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Abstract

A benzyloxypyrimidine derivative represented by general formula (I) or salts thereof; an agricultural / horticultural insecticide comprising said compound as the active ingredient; and a method for using the same. In general formula (I): R1 represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, an alkoxyalkyl group, etc.; R2 or R3 represents a hydrogen atom, an alkyl group, etc.; X represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a haloalkenyl group, a haloalkynyl group, a trialkylsilyl group, etc.; A represents an oxygen atom, etc.; and m represents an integer of 0-5.

Description

Technical field [0001] The present invention relates to agricultural and horticultural pesticides containing novel pyrimidine derivatives or salts thereof as active ingredients and their use methods. Background technique [0002] Although the pyrimidine derivative described in Patent Document 1 is disclosed to be useful as an insecticide, it has a different structure from the pyrimidine derivative of the present invention. Although the pyrimidine derivative described in Patent Document 2 is disclosed as being useful as an insecticide, a compound having the substituent disclosed in the present invention at the 4-position of the pyrimidine is not disclosed. [0003] Patent document 1: WO 2010 / 064688 [0004] Patent document 2: WO 1993 / 006091. Contents of the invention [0005] Problems to be solved by this invention [0006] In crop production in the agricultural and horticultural fields, losses caused by pests are still serious, and due to the occurrence of pests that ar...

Claims

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Application Information

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IPC IPC(8): C07D239/34A01N43/54A01N43/56A01N47/02A01N47/18A01P7/04C07D239/46
CPCA01N43/54A01N43/56A01N43/60C07D239/34C07D239/46C07D239/52C07D239/56C07D401/12C07D403/12A01N43/40
Inventor 笠原良太原山博人佐藤英孝中野元文深津浩介犬饲佳代
Owner NIHON NOHYAKU CO LTD