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Biphenyl bisamide compound as well as preparation method and application thereof

A biphenyl bisamide compound technology, applied in the field of biphenyl bisamide compounds, can solve the problems of few targets and serious pest resistance problems

Inactive Publication Date: 2014-05-07
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the problem of pest resistance is becoming more and more serious due to the fact that the existing insecticides have fewer targets and are used repeatedly for a long time

Method used

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  • Biphenyl bisamide compound as well as preparation method and application thereof
  • Biphenyl bisamide compound as well as preparation method and application thereof
  • Biphenyl bisamide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] (1) Preparation of 2'-formylmethylamino-[1,1'-biphenyl]-2-benzoic acid:

[0067]

[0068] Weigh 672 mg (3 mmol, 1 equivalent) of 2,2'-diphthalic anhydride into a round bottom flask, add 3 mL of DMF and 439 mg (3.6 mmol, 1.2 equivalent) of 2,4,6-trimethylpyridine (Catalyst), after stirring for 2 minutes, add 0.33ml of methylamine solution (3.3mmol, 1.1 equivalent, concentration 31%), after stirring for 3 hours at room temperature, stop the reaction, spin off DMF under reduced pressure, and dissolve the resultant with ethyl acetate. Then it was transferred to a separatory funnel, washed with 2M HCl, and a large amount of solid was precipitated. The white solid was obtained by suction filtration and recrystallization. The yield was 81%.

[0069] 1 H NMR(400MHz,DMSO)δ12.70(s,1H), 8.71(d,J=4.7Hz,1H), 7.59-7.46(m,3H), 7.55-7.29(m,3H), 7.15-7.05( m,2H), 2.63(d,J=4.6Hz,3H).

[0070] HRMS: m / z calculated value C 15 H 14 NO 3 (M+H) + 256.0968, measured value 256.0967

[0071] (2) Prepa...

Embodiment 2

[0078] 4-Ethylthio-N-(2-methoxyphenyl)-N'-methyl-[1,1'-biphenyl]-2,2'-dimethylamide (the compound represented by formula I-2 ) Preparation:

[0079]

[0080] Divide by 4-ethylthio-2,2'-diphthalic anhydride instead of 2,2'-diphthalic anhydride (in step (1)) and 2-methoxyaniline instead of aniline (step (2) Except for middle), the remaining steps are similar to those in Example 1 to obtain the title compound.

[0081] 1 H NMR(400MHz,DMSO)δ9.70(s,1H), 8.58(d,J=4.6Hz,1H), 7.87(dd,J=8.0,1.4Hz,1H), 7.67-7.56(m,2H) ,7.50–7.37(m,3H),7.13–7.08(m,1H), 7.07–7.01(m,1H), 7.01–6.94(m,1H), 6.89–6.77(m,2H), 3.56(s, 3H), 2.64 (d, J=4.6 Hz, 3H) 2.65 (q, J=7.9 Hz, 2H) 1.10 (t, J=7.9 Hz, 3H).

[0082] 13 C NMR (101MHz, DMSO) δ169.82,167.64,149.96,139.73,139.52,136.86,136.30,130.00,129.95,129.91,129.07,128.40,127.99,127.85,127.72,127.67,124.81,121.59,120.44,111.40,55.72,29.4 ,26.47,14.1

[0083] HRMS: m / z calculated value C 24 H 25 N 2 O 3 S(M+H) + 421.1580, the measured value is 421.1582.

Embodiment 3

[0085] N-(3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)-N'-methyl-[1,1'-biphenyl]-2,2 '-Diformamide (the compound represented by formula I-3):

[0086]

[0087] Except that 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline was substituted for aniline (in step (2)), the remaining steps were similar to those in Example 1 to obtain the title compound.

[0088] 1 H NMR(400MHz,DMSO)δ11.20(s,1H), 8.62(d,J=4.7Hz,1H), 7.67-7.59(m,3H), 7.59-7.47(m,3H), 7.47-7.39( m, 2H), 7.23-7.08 (m, 2H), 6.91 (t, J=51.4Hz, 1H), 2.62 (d, J=4.6Hz, 3H).

[0089] 13 C NMR (101MHz, DMSO) δ 170.86,168.24,139.40,139.31,138.96,136.21,136.11,136.09,130.63,130.12,130.05,130.00,129.79,128.25,128.23,128.18,127.51,119.58,26.54,22.52,14.41.

[0090] HRMS: m / z calculated value C 23 H 17 C l2 F 4 N 2 O 3 (M+H) + 515.0552 The measured value is 515.0554.

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Abstract

The invention relates to a biphenyl bisamide compound as well as a preparation method and application thereof. The biphenyl bisamide compound is prepared by reacting 2,2'-diphenic acid anhydride or a derivative thereof with corresponding amines (H2NR1 and H2NR2) respectively. The biphenyl bisamide compound provided by the invention has remarkable insecticidal activity and a selective insecticidal spectrum, is simple in preparation process, and is expected to be developed into a novel pesticide which is low in toxicity, efficient and environment-friendly.

Description

Technical field [0001] The invention relates to a biphenyl bisamide compound and its preparation and use. Background technique [0002] Insecticides are important tools widely used to control harmful insects in agricultural production. In 1998, after screening and structural optimization of phthalamide compounds, the Japanese Pesticide Company and Bayer Company discovered flubendiamide; at the same time, DuPont inverted one of the amides to obtain an excellent insecticidal activity. O-formylaminobenzamide compounds (the representative compound is chlorantraniliprole), their targets are all rinidin receptors. [0003] However, due to the fact that the existing insecticides have fewer targets and are used repeatedly for a long time, the problem of pest resistance has become more and more serious. As environmental protection and food safety have received more and more attention from people, people have put forward higher and higher requirements for the toxicity and environmental fri...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C233/65C07C233/75C07C233/66C07C237/40C07C233/76C07C319/20C07C323/62C07C315/04C07C317/44C07C323/42C07C317/40C07C259/10C07C233/80C07C235/56C07C253/30C07C255/57C07C255/24C07C303/22C07C309/51C07D213/75C07D277/46C07D295/135C07D307/66C07D241/20C07D231/40C07D207/34A01N37/22A01N37/40A01N41/10A01N37/18A01N43/40A01N43/78A01N37/46A01N37/48A01N37/42A01N37/34A01N41/08A01N43/08A01N43/36A01N43/56A01N43/60A01N47/02A01P7/04
Inventor 李忠徐晓勇刘晔雷超邵旭升
Owner EAST CHINA UNIV OF SCI & TECH
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