Benzamide compound and application thereof

A technology of benzamide and compound, applied in the field of benzamide compounds, can solve problems such as unreported insecticidal activity

Active Publication Date: 2019-09-03
メティサバイオテクノロジーカンパニーリミテッド
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In the prior art, there is no report on the compounds shown in the

Method used

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  • Benzamide compound and application thereof
  • Benzamide compound and application thereof
  • Benzamide compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0161] Embodiment 1: the preparation of compound 2.321

[0162]

[0163] Add 0.30 g (7.5 mmol) of 60% sodium hydride to 10 ml of tetrahydrofuran, drop in 0.50 g (0.75 mmol) of 3-benzamido-N-(2,6-dibromo- 4-Heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-1), stirred at room temperature for 10 minutes; added 0.45 g (3.78 mmol) of bromoacetonitrile, and continued to stir at room temperature for 1 hour. After the completion of the reaction monitored by TLC, the reaction was quenched with ice water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and precipitated under reduced pressure. ratio of 1:6~1:2) to obtain 0.38 g of white solid.

[0164] The NMR and mass spectrum data of compound 2.321 are as follows:

[0165] 1 H NMR (600 MHz, internal standard TMS, solvent CDCl 3 ) δ(ppm): 8.10 (t, 1H), 7.98 (d, 1H),7.86 (s, 2H), 7.54 – 7.48(m, 1H), 7.41 – 7.29(m, 4H), 7.28 – 7.21(m , 2H),4.80 (d, 2H).

[0166] 1 H NMR (600MHz, inte...

Embodiment 2

[0181] Embodiment 2: the preparation of compound 3.321

[0182]

[0183] From 3-benzamido-N-(2,6-dichloro-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-2, prepared according to the method reported in WO2010018857) The method for preparing compound 3.321 is the same as that in Example 1.

[0184] The NMR and mass spectrum data of compound 3.321 are as follows:

[0185] 1 H NMR (600MHz, internal standard TMS, solvent CDCl 3 ) δ(ppm): 8.10 (t, 1H), 7.95 (d, 1H),7.67 (s, 2H), 7.49 (t, 1H), 7.41 – 7.34 (m, 3H), 7.31 (t, 1H), 7.29 – 7.22(m, 2H), 4.80 (d, 2H).

[0186] 1 H NMR (600MHz, internal standard TMS, solvent DMSO) δ(ppm): 10.61 (s, 1H), 7.92 (s, 2H),7.70 – 7.58 (m, 2H), 7.42 – 7.27 (m, 6H), 4.93 (s, 2H).

[0187] LC-MS (m / z): 610.0 (m+H).

Embodiment 3

[0188] Embodiment 3: the preparation of compound 6.321

[0189]

[0190] Prepared from 3-benzamido-N-(2-bromo-6-methyl-4-heptafluoroisopropylphenyl)-2-fluorobenzamide (intermediate II-3, referring to the method reported in WO2010018857 Obtained) The method for preparing compound 6.321 is the same as that in Example 1.

[0191] The NMR and mass spectrum data of compound 6.321 are as follows:

[0192] 1 H NMR (600MHz, internal standard TMS, solvent CDCl 3 ) δ(ppm): 8.12-8.06 (m, 1H), 7.90 (d,1H), 7.72 (s, 1H), 7.51 (t, 1H), 7.51 (t, 1H), 7.48 (s, 1H), 7.42 – 7.30 (m, 4H), 7.28 – 7.22 (m, 1H), 4.81 (d, 2H), 2.38 (s, 3H).

[0193] 1 H NMR (600MHz, internal standard TMS, solvent DMSO) δ(ppm): 10.29 (s, 1H), 7.80 (d, 1H),7.70 – 7.64 (m, 2H), 7.59 (t, 1H), 7.38 (d , 3H), 7.35 – 7.27 (m, 3H), 4.93(s, 2H), 2.35 (s, 3H).

[0194] LC-MS (m / z): 634.0 (m+H).

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Abstract

The invention discloses a benzamide compound and application thereof. The structure of the compound is shown as general formula I in the specification, wherein all the substituent groups are defined as the specification. The general formula I compound has a novel structure and excellent insecticidal activity, and can effectively control plutella xylostella, armyworm, chilo suppressalis and other pests at a low dose. The general formula I compound also has unexpected high insecticidal quick-acting performance and takes effect rapidly, can achieve high insecticidal activity 1d after application,and can reach extremely high insecticidal activity in three days, thus having broad application prospects.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides, and in particular relates to a novel benzamide compound and its application. Background technique [0002] Patent JP2007099761A relates to a benzamide compound with insecticidal activity, and specifically discloses the following structures: CK1 (compound number: 1-23), CK2 (compound number: 1-24) and CK3 (compound number: 1- 206). [0003] [0004] [0005] Patent CN102112437A discloses the following general formula compounds and specific compounds CK4 (compound number: 6-18), CK5 (compound number: 1-128), CK6 (compound number: 1-163), CK7 (compound number: 1-171) , CK8(Compound No.: 7-130), CK9(Compound No.: 7-135), CK10(Compound No.: 7-169), CK11(Compound No.: 7-174), CK12(Compound No.: 8-111) , CK13 (Compound No.: 8-146), CK14 (Compound No.: 8-155), have certain insecticidal activity: [0006] [0007] [0008] [0009] [0010] [0011] [0012] Patent...

Claims

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Application Information

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IPC IPC(8): C07C255/29A01N37/46A01P7/04
CPCC07C255/29A01N37/46C07C255/57Y02A50/30A01N25/06A01N37/22A01N37/34C07C237/40
Inventor 张立新张静张熹晗高一星汪杰康卓
Owner メティサバイオテクノロジーカンパニーリミテッド
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