Pyrimidine derivatives, horticultural insecticides comprising said derivatives and method of use thereof

A technology of pyrimidine derivatives, C1-C6, applied in the directions of pesticides, botanical equipment and methods, medical preparations containing active ingredients, etc., can solve problems such as no teaching or disclosure of insecticidal activity

Inactive Publication Date: 2012-01-04
NIHON NOHYAKU CO LTD
View PDF7 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, they are not taught or disclosed in any prior art do...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Pyrimidine derivatives, horticultural insecticides comprising said derivatives and method of use thereof
  • Pyrimidine derivatives, horticultural insecticides comprising said derivatives and method of use thereof
  • Pyrimidine derivatives, horticultural insecticides comprising said derivatives and method of use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[1152] (1-1) Production of 2-chloro-4-(4-tert-butylphenyl)-5-methoxypyrimidine

[1153]

[1154] Combine 4-tert-butylphenylboronic acid (3.98 g, 0.022 mol), sodium carbonate (7.00 g, 0.066 mol), 2,4-dichloro-5-methoxypyrimidine (4.0 g, 0.022 mol) and tetrakis ( Triphenylphosphine) palladium (2.54 g, 0.0022 mol) was added to a mixed solvent of acetonitrile (60 mL) and water (40 mL). The reaction vessel was replaced with argon, and the mixture was reacted under reflux with heating for 3 hr. The mixture was cooled to room temperature and poured into water. The mixture was extracted with methyl tert-butyl ether and washed with saturated brine. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography to provide the target product (4.33 g),

[1155] Yield: 71%

[1156] Physical properties: melting point m.p. = 77-79°C.

[1157] (1-2) Preparation of 4-(4-tert-butylphenyl)-5-methoxypyrimi...

Embodiment 2

[1162] Example 2. Preparation of 4-(4-tert-butylphenyl)-5-hydroxypyrimidine (Compound No. 1-1)

[1163]

[1164] Add 4-(4-tert-butylphenyl)-5-methoxypyrimidine (1.40 g, 5.78 mmol) and lithium iodide (2.48 g, 18.5 mmol) to 2,4,6-trimethylpyridine ( 6 mL), react under heating and reflux for 8 hr. The mixture was cooled to room temperature and poured into 3N hydrochloric acid (30 ml). The mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography to provide the target product (0.73 g),

[1165] Yield: 55%

[1166] Physical properties: melting point m.p. = 104-106°C.

Embodiment 3

[1167] Example 3. Preparation of 4-(4-tert-butylphenyl)-5-n-propoxypyrimidine (Compound No. 1-86)

[1168]

[1169] Add 4-(4-tert-butylphenyl)-5-hydroxypyrimidine (0.37 g, 1.62 mmol), n-propanol (0.18 g, 2.43 mmol) and triphenylphosphine (0.64 g, 2.43 mmol) to tetrahydrofuran (5 mL), and diethyl azodicarboxylate (1.06 g, 2.43 mmol) was added dropwise to the solution. Then, the mixture was reacted at room temperature for 2 hr. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to provide the target product (0.27 g),

[1170] Yield: 62%

[1171] Physical properties: refractive index n D = 1.5618 (25.5°C).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to view more

Abstract

Pyrimidine derivatives represented by general formula (I) shown in the description, wherein R1 represents an H, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, haloalkyl group, halocycloalkyl group, haloalkenyl group, haloalkynyl group, alkoxyalkyl group, etc. A represents -O-, -S-, -SO-, or -SO2-; R2 represents a halogen atom, hydroxyl group, cyano group, nitro group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, haloalkyl group, haloalkenyl group, haloalkynyl group, halocycloalkyl group, etc. m represents an integer 0 or 1; n represents an integer 0-4; and X represents a nitrogen atom or -CH-. and salts thereof have excellent insecticidal and miticidal activity and are effective as the active ingredient in horticultural insecticides.

Description

Technical field [0001] The present invention relates to an agrohorticultural insecticide containing a novel pyrimidine derivative and its salt as effective ingredients, or a method of using the same. Background technique [0002] Patent Documents 1 and 2 respectively describe that pyrimidine derivatives can be used as antibacterial agents and herbicides. However, they are structurally different from the pyrimidine derivatives of the present invention. Patent Document 3 describes that pyrimidine derivatives can be used as herbicides. However, the substituent at the 5-position of pyrimidine does not include the substituent disclosed in the pyrimidine derivative of the present invention. In addition, there is no teaching or disclosure in any prior art documents that they have the insecticidal activity as in the present invention. [0003] Patent Document 1: WO2007 / 148093 [0004] Patent Document 2: WO2005 / 40152 [0005] Patent Document 3: WO2002 / 38550. Summary of the invention [000...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D239/34A01N43/54A01P7/04A61K31/505A61K31/506A61P33/14C07D239/36C07D239/38C07D401/04
CPCC07D239/34A01N43/54C07D239/38C07D239/36C07D401/04A61P33/00A61P33/14A61K31/505A61K31/506C07D405/10
Inventor 原山博人佐藤英孝八十川伯朗中野元文犬饲佳代深津浩介笠原良太
Owner NIHON NOHYAKU CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap