Oxime ether derivative and bactericide for agricultural and horticultural use

A kind of technology of derivatives and oxime ethers, applied in the field of oxime ether derivatives and their salts, and agricultural and horticultural fungicides, can solve the problems such as no compounds are given, manufacture examples and examples are not specifically recorded, and the effect is reliable and excellent. Control effect, toxicity and effect with low environmental impact

Inactive Publication Date: 2011-07-06
NIPPON SODA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] However, in this document, for the case where Q1 is formula (3), the production examples and examples are not specifically described, nor are any specific compounds given.

Method used

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  • Oxime ether derivative and bactericide for agricultural and horticultural use
  • Oxime ether derivative and bactericide for agricultural and horticultural use
  • Oxime ether derivative and bactericide for agricultural and horticultural use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0500] Production of methyl N-(2-chloro-5-{1-[3-fluoro-2-(trifluoromethyl)benzyloxyimino]ethyl}phenoxy)carbamate (compound 1-13)

[0501] (Process 1)

[0502] Production of tert-butyl N-[3-fluoro-2-(trifluoromethyl)benzyloxy]carbamate

[0503]

[0504] Add 20ml of acetonitrile, 0.63g of N-tert-butoxycarbonyl hydroxylamine, 1,8-diazabicyclo[5.4.0]-7-deca to 1.00g of 3-fluoro-2-(trifluoromethyl)benzyl bromide Monocarbene (DBU) 0.72g, stirred at room temperature for 3 hours. After completion of the reaction, ethyl acetate was added, followed by washing with 7% hydrochloric acid and 10% aqueous sodium hydroxide solution in this order. The obtained organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain 1.20 g of the target crude N-[3-fluoro-2-(trifluoromethyl)benzyloxy]carbamate tert-butyl ester .

[0505] (Process 2)

[0506] Production of methyl N-(2-chloro-5-{1-[3-fluoro-2-(trifluoromethyl)benzyloxyimi...

Embodiment 2

[0510] Production of methyl N-{2-chloro-5-[1-(2-iodobenzyloxyimino)ethyl]phenoxy}carbamate (compound 11-9)

[0511] (Process 1)

[0512] Production of tert-butyl N-(2-iodobenzyloxy)carbamate

[0513]

[0514] Add 20 ml of acetonitrile, 0.55 g of N-tert-butoxycarbonyl hydroxylamine, and 0.62 g of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) into 1.00 g of 2-iodobenzyl bromide, Stir at room temperature for 1 hour. After completion of the reaction, ethyl acetate was added, followed by washing with 7% hydrochloric acid and 10% aqueous sodium hydroxide solution in this order. The obtained organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain 1.08 g of the target crude tert-butyl N-(2-iodobenzyloxy)carbamate (crude yield 92%).

[0515] (Process 2)

[0516] Production of methyl N-{2-chloro-5-[1-(2-iodobenzyloxyimino)ethyl]phenoxy}carbamate

[0517]

[0518] A mixture of 0.30 g of methyl N-(5-acetyl-2-chloro...

Embodiment 3

[0520] Production of methyl N-{2-methyl-5-[1-(2-trifluoromethylbenzyloxyimino)ethyl]phenoxy}carbamate (compound 21-24)

[0521] (Process 1)

[0522] Production of 4-bromo-2-(4-methoxybenzyloxy)-1-methylbenzene

[0523]

[0524] 30.0 g of 4-bromo-2-fluorotoluene and 23.1 g of p-methoxybenzyl alcohol were dissolved in 240 ml of DMI (dimethylimidazolinone), and 6.68 g of sodium hydride was added under ice cooling, and stirred at 110°C for 1 hour. After cooling to room temperature, the reaction solution was poured into aqueous ammonium chloride solution, and extracted with ethyl acetate. Magnesium sulfate was added to the organic layer to dry, and after filtration, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=9:1) to obtain the target 4-bromo- 42.8 g of 2-(4-methoxybenzyloxy)-1-methylbenzene (88% yield).

[0525] (Step 2) Production of 1-[3-(4-methoxy...

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PUM

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Abstract

A bactericide for agricultural and horticultural use containing an oxime ether derivative represented by formula (I) or at least one salt thereof. (In formula (I), X represents a halogen atom, a C1-20 alkyl group or the like; R1 and R2 each represents a hydrogen atom, a C1-20 alkyl group or the like; R3 represents a hydrogen atom, a C1-20 alkyl group or the like; R4 represents a hydrogen atom, a C1-20 alkyl group or the like; R5 represents a hydrogen atom or the like; Y represents an oxygen atom or the like; Z represents an oxygen atom or the like; Q represents an aryl group or the like; m represents an integer of 0-8; and n represents an integer of 0-4).

Description

technical field [0001] The present invention relates to novel oxime ether derivatives and their salts, and an agricultural and horticultural fungicide containing at least one of these compounds as an active ingredient. [0002] This application is based on Japanese Patent Application No. 2008-207297 filed in Japan on August 11, 2008, Japanese Patent Application No. 2008-207304 filed in Japan on August 11, 2008, and Japanese Patent Application No. 2008-207304 filed in Japan on September 24, 2008. Japanese Patent Application No. 2008-244957 claims the right of priority, and its contents are incorporated herein. Background technique [0003] When cultivating agricultural and horticultural crops, many control agents are used for crop diseases, but their control effects are insufficient, or their use is limited due to the emergence of drug-resistant pathogenic bacteria, or phytotoxicity or pollution occurs to plants, or from From the point of view of the toxicity of humans, live...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/08A01N47/24A01P3/00
CPCA01N47/24C07C271/08C07C251/48
Inventor 古川裕纪桑原赖人金泽润佐藤元亮
Owner NIPPON SODA CO LTD
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