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Heptafluoroisopropyl-containing carbonyl oxime ether compound, preparation method and applications thereof

A technology of heptafluoroisopropyl and carbonyl oxime ether, which is applied in the direction of botany equipment and methods, applications, chemicals for biological control, etc., and can solve the problems that do not describe the use of insect pests and diseases, insecticidal and bactericidal activities No public issues

Active Publication Date: 2015-06-24
ZHEJIANG RES INST OF CHEM IND CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Literature (Journal of Enzyme Inhibition and Medicinal Chemistry, 2009, 24(5), 1141-1147.) reported oxime compounds similar to the present invention, but only studied the anti-oxidation and free radical scavenging activities of such compounds, and did not describe Its use for agricultural pest control and disease prevention
[0005] In the prior art, the preparation of the heptafluoroisopropyl-containing carbonyl oxime ether compound represented by the general formula (I) of the present invention and its insecticidal and bactericidal activities have not been disclosed

Method used

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  • Heptafluoroisopropyl-containing carbonyl oxime ether compound, preparation method and applications thereof
  • Heptafluoroisopropyl-containing carbonyl oxime ether compound, preparation method and applications thereof
  • Heptafluoroisopropyl-containing carbonyl oxime ether compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] Preparation of N-hydroxy-2-(3-chlorophenyl)-N’-[2-methoxy-4-heptafluoroisopropyl-phenyl]-2-oxo-acetamide (compound 60)

[0099] Step 1: Synthesis of m-chlorobenzene-α-chloro-α-carbonyl oxime

[0100]

[0101] Weigh 0.1mol of m-chloroacetophenone and 150.0g of dry dioxane in a 250mL dry three-neck flask for ice bathing. Add a drying tube above the reaction bottle. When the temperature of the reaction system is around 0°C, feed hydrogen chloride gas and adjust the gas flow rate to stabilize at 2 to 3 bubbles per second. After the gas flow is stable, slowly drop in 0.3 mol of isoamyl nitrite to ensure that the temperature of the reaction system is below 5°C. After dropping, continue to ventilate the gas, and you will find that the color of the reaction solution changes from colorless to deep red, indicating that saturated hydrogen chloride gas is dissolved in the reaction solution. Stop the gas flow, let the reaction solution continue to react at 0-5°C for about 1 ho...

Embodiment 2

[0106] Preparation of N-hydroxyl-2-(4-methoxy-phenyl)-N'-[2-methoxy-4-heptafluoroisopropyl-phenyl]-2-oxo-acetamide (compound 26)

[0107] Step 1: Synthesis of p-methoxybenzene-α-chloro-α-carbonyl oxime

[0108]

[0109] Using p-methoxyacetophenone as the raw material, the experimental procedure is the same as that in Example 1 for the synthesis of intermediate chlorobenzene-α-chloro-α-carbonyl oxime to obtain a white solid with a yield of 84.8%, m.p.116-118°C; 1 H NMR (400MHz, DMSO-d 6 ), δ: 3.85(s,3H,OCH 3 ), 6.99 (d, 2H, J=8.80Hz, Ar-H), 7.90 (d, 2H, J=8.80Hz, Ar-H), 13.64 (s, 1H, OH).

[0110] Step 2: Synthesis of target compound

[0111]

[0112] Taking p-methoxybenzene-α-chloro-α-carbonyl oxime and 2-methoxy-4-heptafluoroisopropylaniline as raw materials, the experimental procedure is the same as the synthesis of compound 60 in step 2 of Example 1 to obtain light Yellow solid, yield 84.3%.

Embodiment 3

[0114] N-(4-chlorobenzyloxy)-N'-(2,6-dimethyl-4-heptafluoroisopropyl-phenyl)-2-furan-2-yl-2-oxo-acetamide Preparation of (Compound 103)

[0115] Step 1: Synthesis of 2-furyl-α-chloro-α-carbonyl oxime

[0116]

[0117] Using 2-furanoacetophenone as the raw material, the experimental procedure was the same as the synthesis of intermediate chlorobenzene-α-chloro-α-carbonyl oxime in Example 1 to obtain a black solid with a yield of 81.8%, m.p.124-126°C; 1 H NMR (400MHz, DMSO-d 6 ), δ: 6.78 (m, 1H, Ar-H), 7.57 (d, 1H, Ar-H), 8.13 (d, 1H, Ar-H), 13.62 (s, 1H, OH).

[0118] Step 2: Synthesis of N-(2,6-dimethyl-4-heptafluoroisopropyl-phenyl)-2-furan-2-yl-N’-hydroxy-2-oxo-acetamide

[0119]

[0120] Using 2-furyl-α-chloro-α-carbonyl oxime and 2,6-dimethyl-4-heptafluoroisopropylaniline as raw materials, the experimental procedure is the same as the synthesis of compound 60 in step 2 of Example 1 to obtain Pale yellow solid, yield 82.1%.

[0121] Step 3: Synthesis of target co...

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Abstract

The present invention discloses a heptafluoroisopropyl-containing carbonyl oxime ether compound, which has the following structural general formula (I), wherein each substituent is defined in the instruction. The present invention further provides a preparation method and applications of the compound. The compound of the present invention is particularly suitable for prevention and control of Mythimna separate, AphiscraccivoraKoch, Tetranychus cinnabarinus, cucumber downy mildew bacteria and rice sheath blight disease bacteria.

Description

technical field [0001] The invention belongs to the field of insecticides and fungicides, and relates to a carbonyl oxime ether compound containing heptafluoroisopropyl group, its preparation method and application. Background technique [0002] Oxime compounds have excellent insecticidal, bactericidal, herbicidal, and anti-plant virus activities, and many varieties also have the advantages of low toxicity and low residue. In the 1990s, oxime pesticides developed rapidly, and a large number of fungicides and herbicides were developed. At present, the molecular design, synthesis and biological activity research of oxime compounds are still one of the hotspots in the creation of pesticides. [0003] Fluorine atoms have special chemical and biological properties. The introduction of fluorine-containing groups or fluorine atoms has a significant impact on the physical and chemical properties and physiological activities of compounds. It has been found that the introduction of ...

Claims

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Application Information

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IPC IPC(8): C07C259/14A01N37/52A01P3/00A01P7/02A01P7/04
Inventor 朱冰春姬文娟袁静胡伟群黄红英孔小林陈杰魏优昌
Owner ZHEJIANG RES INST OF CHEM IND CO LTD
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