Substituent indole compound and application thereof

A technology of compounds, indoles, applied in applications, organic chemistry, biocides, etc., which can solve problems such as structural differences

Active Publication Date: 2010-06-23
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The compound reported in this patent can be used as an agricultural fungicide, but the

Method used

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  • Substituent indole compound and application thereof
  • Substituent indole compound and application thereof
  • Substituent indole compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0133] Example 1: Preparation of compound 35

[0134] (1) Synthesis of intermediate (V-A)

[0135]

[0136] Add 7.0 g of p-fluoroaniline to 20 ml of oxalyl chloride, heat at 165°C for 30 minutes, distill the excess oxalyl chloride to obtain a light yellow oil, let stand to cool, add a small amount of methanol, solids precipitate, filter, and methanol wash The target product is 8.3 g, yield: 80%.

[0137] (2) Synthesis of intermediate (IV-A)

[0138]

[0139] Heat 2.2 g of 5-fluoroindole-2,3-dione (VA) with 4 ml of 85% hydrazine hydrate in ethanol solution for 4 hours at reflux, add 2.8 g of sodium hydroxide, and continue the reaction 4 After hours, it was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. Under reduced pressure distillation, 1.5 g of yellow solid was obtained, the melting point was 143-145°C, and the yield was 74.6%.

[0140] (3) Synthesis of compound 35

[0141]

[0142] Under the ice-salt bath, slowly drop 1.2 g of phosphorus oxychloride into t...

example 2

[0144] Example 2: Preparation of compound 41

[0145]

[0146] Add 1 g of 2-chloro-5-fluoroindole-3-carbaldehyde (Compound 35) into the reaction flask, add 0.4 g of hydroxylamine hydrochloride, 0.2 g of sodium hydroxide, 40 ml of ethanol, and heat at 80°C with stirring and reflux for reaction. After the reaction was completed, the reaction solution was poured into water and extracted with ethyl acetate to obtain 0.8 g of yellow solid, yield: 64.7%.

example 3

[0147] Example 3: Preparation of compound 46

[0148]

[0149] At room temperature, 0.2 g of compound 41 was added to 0.3 g of p-toluic acid in methylene chloride solution, and 0.5 g of triethylamine was added. React at room temperature for 2 hours. Extract with dichloromethane, wash with saturated sodium bicarbonate, and dry with anhydrous magnesium sulfate. Concentrated to obtain 0.11 g of red solid, melting point 150-154°C, yield: 35.4%. The NMR data are as follows:

[0150] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm): 8.68(s, 1H, NH), 7.91(s, 1H, CH), 7.85-7.28(m, 7H, Ar-H), 2.43(s, 3H, CH) 3 ).

[0151] The physical and chemical properties and nuclear magnetic data of some compounds ( 1 HNMR, 300MHz, internal standard TMS, solvent CDCl 3 )as follows:

[0152] Compound 1: Melting point is 266-268°C. δ ppm 9.97 (s, 1H, CHO), 8.02 (d, 1H, indole-4-H), 7.46 (dd, 1H, indole-7-H), 7.32 (dd, 1H, indole-6-H).

[0153] Compound 22: Melting point is 260-262°C. δ ppm ...

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Abstract

The invention discloses a substituent indole compound which is structurally shown as a general formula (I): the definition of each substituent group refers to an instruction manual. The compound has the bactericidal and insecticidal activity. The compound and another compound containing the compound as an active component are adopted for preventing and treating diseases of various crops and particularly have better prevention effect on pyriculariagrisea. A part of compound also has the insecticidal and acaricidal activity and can be used for preventing and treating pests and mites on the various crops.

Description

Technical field [0001] The invention belongs to the field of agricultural fungicides and pesticides, and specifically relates to a substituted indole compound and its application. Background technique [0002] Indole compounds are known to have biological activity in medicine. Patents CN101157688, DE 2707268, US 5464861, US 20050054631, US 5852014, US 4148895, WO 03106462, WO 2005034943, etc. all have reports of indole compounds; journal articles such as Journal of Medicinal Chemistry (1977), 20(10), 1344 -6; Journal of Medicinal Chemistry (2002), 45(12), 2666-2669; European Journal of Medicinal Chemistry (2004), 39(9), 785-791, etc. There are also reports of indole compounds. [0003] Patent JP 02085251 discloses the following general formula compounds as plant growth regulators: [0004] [0005] Patent US 20040143116 (CN 1550499) reports an indole group-containing compound of the following general formula: [0006] [0007] The compound reported in this patent can be used as an a...

Claims

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Application Information

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IPC IPC(8): C07D209/10C07D401/12A01N43/38A01P3/00A01P7/00
Inventor 刘长令刘远雄李志念杨吉春张弘
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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