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Alkoxy hexafluoroisopropyl-containing phthalic diamide compounds and application thereof

A technology containing alkoxyhexafluoroisopropyl and alkoxyhexafluoroisopropyl, which is applied in the field of organic synthesis and preparation, can solve the problems of high synthesis cost, high price, and reduced fat solubility of compounds, and achieve strong insecticide The effect of activity, low cost and simple preparation

Active Publication Date: 2019-09-24
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Flubendiamide also has some disadvantages that lead to limitations in the further promotion of this insecticide: (1) the synthesis cost is high, and the key intermediate heptafluoroisopropyl iodide (C 3 f 7 I) expensive, low boiling point is not easy to transport and preserve
(2) There is a risk to aquatic invertebrates such as Daphnia magna, which affects the safety of the aquatic environment, so it is prohibited to register and use on rice
However, after the fluorine atom is replaced by a hydroxyl group, the fat solubility of the compound is reduced, which is not conducive to the preparation of dosage forms, thus affecting its efficacy.

Method used

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  • Alkoxy hexafluoroisopropyl-containing phthalic diamide compounds and application thereof
  • Alkoxy hexafluoroisopropyl-containing phthalic diamide compounds and application thereof
  • Alkoxy hexafluoroisopropyl-containing phthalic diamide compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 3-iodo-N'-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-N-{2-methyl-4-[2,2,2-trifluoro-1-methyl Synthesis of oxy-1-(trifluoromethyl)ethyl]phenyl}phthalamide (a compound represented by formula Ia, abbreviated as compound Ia, the same below):

[0036]

[0037] Hexafluoroacetone trihydrate (4.84 g) and p-toluenesulfonic acid (0.2 g) were dissolved in 10 ml of xylene, and o-methylaniline (2.14 g) was added dropwise at 90°C. The reaction solution was stirred for 12 hours at a temperature of 130°C, and the reaction was followed by TLC. After the reaction, the reaction solution was cooled to room temperature, the crystals were filtered, and the filter cake was washed with petroleum ether to obtain 2-(3'-methyl-4'-aminophenyl)-1,1,1,3,3, The 3-hexafluoro-2-propanol compound represented by formula V is about 5.16 g, and the yield is 95%.

[0038] Add 2.73 grams of 2-(3'-methyl-4'-aminophenyl)-1,1,1,3,3,3-hexafluoro-2-propanol compound represented by formula V and 4.89 grams of cesium carb...

Embodiment 2

[0046] 3-iodo-N'-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-N-{2-methyl-4-[2,2,2-trifluoro-1-ethane Synthesis of oxy-1-(trifluoromethyl)ethyl]phenyl}phthalamide (compound Ib):

[0047]

[0048] The preparation method was the same as that in Example 1. In the synthesis of VIb, ethyl iodide was used to replace methyl iodide in Example 1 to obtain a white solid (Compound Ib). The total yield of the three-step reaction was 63%, and the melting point was 136.7-138.9°C.

[0049] 1 H NMR(400MHz, DMSO-d 6 )δ=9.73(s,1H),8.43(s,1H),8.03(d,J=8.0Hz,1H),7.84(d,J=8.0Hz,1H),7.74(d,J=7.2Hz, 1H),7.46–7.44(m,2H),7.29(t,J=8.0Hz,1H),3.68(s,2H),3.63(q,J=6.8Hz,2H),2.95(s,3H), 2.38(s,3H),1.57(s,6H),1.32(t,J=6.8Hz,3H)ppm;

[0050] 13 C NMR(100MHz, DMSO-d 6 )δ=167.6, 165.5, 141.2, 140.7, 138.3, 136.0, 132.3, 130.1, 129.4, 127.3, 125.6, 124.7, 123.7, 123.6, 95.3, 82.1, 62.3, 60.7, 52.4, 43.0, 26.1, 18.1, 14.9ppm;

[0051] 19 F NMR(376MHz, DMSO-d 6 )δ=–70.4(s,6F)ppm.

[0052] HRMS(ESI): C 25 H 27 F 6 IN 2 O 5 SNa[...

Embodiment 3

[0054] 3-iodo-N'-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-N-{2-methyl-4-[2,2,2-trifluoro-1-normal Synthesis of propoxy-1-(trifluoromethyl)ethyl]phenyl}phthalamide (compound Ic):

[0055]

[0056] The preparation method is the same as that in Example 1. In the synthesis of VIc, 1-bromopropane was used to replace methyl iodide in Example 1 to obtain a white solid (Compound Ic). The total yield of the three-step reaction was 61%, and the melting point was 142.1-145.0°C.

[0057] 1 H NMR(400MHz, DMSO-d 6 )δ=9.72(s,1H), 8.41(s,1H), 8.02(d,J=7.6Hz,1H), 7.81(d,J=8.0Hz,1H), 7.72(d,J=7.6Hz, 1H),7.44–7.42(m,2H),7.28(t,J=7.6Hz,1H), 3.65(s,2H), 3.51(t,J=6.4Hz,2H), 2.94(s,3H), 2.36(s,3H),1.73-1.68(m,2H),1.54(s,6H),0.95(t,J=7.6Hz,3H)ppm;

[0058] 13 C NMR(101MHz, DMSO-d 6 )δ=167.7,165.5,141.3,140.7,138.3,136.1,132.4,130.1,129.5,127.3,125.7,124.8,123.7,123.5,95.4,82.1,67.7,60.8,52.4,43.1,26.1,22.4,18.1,10.0 ppm;

[0059] 19 F NMR(376MHz, DMSO-d 6 )δ=–70.3(s,6F)ppm.

[0060] HRMS(ESI): C 26 H 29 F 6 ...

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Abstract

The invention discloses alkoxy hexafluoroisopropyl-containing phthalic diamide compounds having the structure shown as a formula I, wherein R is selected from a C1-C6 linear or branched alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group. Among the provided alkoxy hexafluoroisopropyl group-containing phthalic diamide compounds, many compounds have high insecticidal activity and the insecticidal effect comparable to that of flubendiamide.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis preparation, and specifically relates to a phthalamide compound containing an alkoxy hexafluoroisopropyl group and its application in plant protection. Background technique [0002] Pesticides play an irreplaceable role in the protection of crops and in ensuring high yields and harvests. Traditional pesticides have been greatly restricted in plant protection due to problems such as high toxicity, high residue, and "three causes" effects. In addition, unreasonable mixing and abuse of pesticides have led to increased resistance and reduced pesticide control effects. Therefore, the development of high-efficiency, low-toxicity, low-residue, non-resistant and novel mechanism of action insecticides has become an important research field in the creation of pesticides. [0003] Flubendiamide is an insecticide jointly developed by Japan Pesticide Company and Bayer Crop Science. It is different from o...

Claims

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Application Information

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IPC IPC(8): C07C317/28C07C315/02C07D303/22C07D209/48C07C215/68C07C213/00C07C217/76C07C213/06A01N41/10A01N43/20A01P7/04
CPCA01N41/10A01N43/20C07C213/00C07C213/06C07C315/02C07C317/28C07D209/48C07D303/22C07C215/68C07C217/76
Inventor 曹松赵祥虎贺菁菁李佳录刘熠森李春梅徐思学黄青春
Owner EAST CHINA UNIV OF SCI & TECH
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