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Biphenyl bisamide compounds and their preparation and use

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

Inactive Publication Date: 2016-01-20
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 compounds and their preparation and use
  • Biphenyl bisamide compounds and their preparation and use
  • Biphenyl bisamide compounds and their preparation and use

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'-biphenyl dicarboxylic anhydride and put it in a round bottom flask, add 3 mL of DMF and 439 mg (3.6 mmol, 1.2 equivalent) of 2,4,6-collidine (catalyst), after stirring for 2 minutes, add 0.33ml of methylamine solution (3.3mmol, 1.1 equivalent, concentration 31%), stir at room temperature for 3 hours, stop the reaction, spin off DMF under reduced pressure, and dissolve the resultant with ethyl acetate, Then transferred to a separatory funnel, washed with 2M HCl, a large amount of solid precipitated out, suction filtered and recrystallized to obtain a white solid with a yield of 81%.

[0069] 1 HNMR(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) Preparation of N-...

Embodiment 2

[0078] 4-Ethylthio-N-(2-methoxyphenyl)-N'-methyl-[1,1'-biphenyl]-2,2'-dicarboxamide (compound shown in formula Ⅰ-2 ) preparation:

[0079]

[0080] Divide by 4-ethylthio-2,2'-biphenyl dicarboxylic anhydride instead of 2,2'-biphenyl dicarboxylic anhydride (in step (1)) and 2-methoxyaniline instead of aniline (in step (2) Middle), the remaining steps were similar to Example 1 to obtain the title compound.

[0081] 1 HNMR(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=4.6Hz, 3H). 2.65(q, J=7.9Hz, 2H) 1.10(t, J=7.9Hz, 3H).

[0082] 13 CNMR(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, measured value 421.1582.

Embodiment 3

[0085] N-(3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl)-N'-methyl-[1,1'-biphenyl]-2,2 Preparation of '-diformamide (compound shown in formula Ⅰ-3):

[0086]

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

[0088] 1 HNMR(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 CNMR(101MHz,DMSO)δ170.86,168.24,139.40,139.31,138.96,136.21,136.11,136.09,130.63,130.12,130.05,130.00,129.79,128.25,128.23,128.18,127.51,119.58,26.54,22.52,14.41.

[0090] HRMS: m / z calculated value C 23 h 17 C l2 f 4 N 2 o 3 (M+H) + 515.0552 Found 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 in agricultural production to control harmful insects. In 1998, Nippon Pesticides and Bayer discovered flubendiamide (flubendiamide) after the screening and structural optimization of phthalamide compounds; at the same time, DuPont reversed one of the amides to obtain a compound with excellent insecticidal activity. The o-formamidobenzamide compounds (representative compound is chlorantraniliprole), their targets are all ryanodine receptors. [0003] However, due to the fact that existing insecticides have fewer targets and are used repeatedly for a long time, the problem of pest resistance is becoming more and more serious. As environmental protection and food safety have attracted more and more attention, people have put forward higher and higher requirements for the toxicity and environmental...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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