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A kind of milbemycin analog and its preparation method and application in pesticide

A technology of milbemycin and analogues, applied in the field of milbemycin analogues and their preparation, can solve the problems of high cost, paralysis and death of insects, limited sources of milbemycin, etc., and achieve reduced synthesis costs and high contact kill active effect

Inactive Publication Date: 2016-03-23
INST OF PLANT PROTECTION GANSU ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the mechanism of action of milbemycin is different from that of abamectin, it can cause the opening of glutamate-gated chloride channel (Glutamate-gated chloride), thereby increasing the influx of chloride ions and making normal actions The electric potential cannot be released, causing paralysis and death of the insects, so that it still has a very good killing effect on the resistant mites, which is exactly what avermectin and ivermectin cannot match [(1) Fisher, M.H. Pure & Appl. Chem. 1990, 62 , 1231-1240; (2) Pitterna, T., etal . Bioorg. Med. Chem. 2009, 17 ,4085–4095], but the source of milbemycin in the domestic market is limited and the cost is high

Method used

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  • A kind of milbemycin analog and its preparation method and application in pesticide
  • A kind of milbemycin analog and its preparation method and application in pesticide
  • A kind of milbemycin analog and its preparation method and application in pesticide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of (7a)

[0025] The specific process is as follows:

[0026] Synthesis of Intermediate 2: Dissolve 2 g (2.25 mmol) of ivermectin in 39.6 mL of dry methanol, add 0.4 mL of concentrated sulfuric acid dropwise in an ice bath, and react at 0°C for 30 min after the addition is complete , and then stirred at room temperature for about 16 h, TLC detected that the reaction was complete. Diluted with dichloromethane, with 5% NaHCO 3 aqueous solution, and then the aqueous layer was washed with CH 2 Cl 2 After repeated extraction, the organic layers were combined, and the organic layer was washed with water and saturated brine successively. The organic layer was collected, dried with anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product. The crude product was purified by silica gel column chromatography (200-300 mesh) to obtain 1.4 g of the desired pure product.

[0027] Synthesis of Intermediate 3: Dissolve 5.86g (10mmol) of Intermedia...

Embodiment 2

[0034] Synthesis of (7b)

[0035] The experimental procedure is the same as in Example 1, except that p-toluenesulfonyl azide is replaced by p-chlorophenylsulfonyl azide, and phenylacetylene is replaced by p-methylphenylacetylene (CAS: 766-97-2). The detection data of the product obtained by the reaction are as follows:

[0036] Yield: 61%; white solid, melting point: 137-139°C; 1 HNMR (400MHz, CDCl 3 ) δ :7.85(d,2H, J =8.4,Ar-H),7.43(d,2H, J =8.4,Ar-H),7.18(d,2H, J =8.4,Ar-H),7.01(d,2H, J =8.4,Ar-H),5.67-5.70(m,1H,10-H),5.52-5.55(m,1H,9-H),5.30-5.41(m,3H,3-H,11-H, 19-H),4.56-4.67(m,3H,8a-H,15-H),4.38-4.43(m,1H,-CH 2 C=N-),4.25-4.30(m,2H,5-H,-CH 2 C=N-),4.20(s,1H,13-H),3.93(d,1H, J =6.0,6-H),3.89(s,3H,Ar-CH 3 ),3.78(s,1H,7-OH),3.51-3.53(m,1H,17-H),3.20-3.23(m,2H,2-H,25-H),2.62-2.63(m,1H ,12-H),2.17-2.31(m,4H,5-OH,16-H,24-H),1.25-1.87(m,17H,4-Me,14-Me,20-H,26-H ,27-H,22-H,23-H,18-H),0.70-1.19(m,12H,12-Me,27-Me,24-Me,26-Me); MS-ESI m / z :891.3[M+H] + .

Embodiment 3

[0038] Synthesis of (7c)

[0039] The experimental procedure is the same as in Example 1, except that p-toluenesulfonyl azide is replaced by methylsulfonyl azide. The detection data of the product obtained by the reaction are as follows:

[0040] Yield: 49%; white solid, melting point: 133-135 ℃ ; 1 HNMR (400MHz, CDCl 3 ) δ :7.40-7.49(m,2H,Ar-H),7.32-7.39(m,3H,Ar-H),5.67-5.74(m,1H,10-H),5.53-5.55(m,1H,9- H),5.11-5.42(m,3H,3-H,11-H,19-H),4.57-4.67(m,3H,8a-H,15-H),4.40-4.48(m,1H,- CH 2 C=N-),4.27-4.35(m,2H,5-H,-CH 2 C=N-),4.11-4.13(m,1H,13-H),3.92-3.98(m,1H,6-H),3.50(s,3H,-SO 2 CH 3 ),3.20-3.23(m,1H,7-OH),3.07-3.12(m,1H,17-H),3.02-3.04(m,2H,2-H,25-H),2.64-2.65(m ,1H,12-H),2.19-2.32(m,4H,5-OH,16-H,24-H),1.26-1.90(m,17H,4-Me,14-Me,20-H,26 -H,27-H,22-H,23-H,18-H),0.70-1.05(m,12H,12-Me,27-Me,24-Me,26-Me); MS-ESI m / z :781.6[M+H] + .

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Abstract

The invention discloses milbemycins analogues as well as a preparation method and application thereof in pesticides. The new milbemycins analogues have the following structural formula shown the specification, wherein R1 is 2-naphthyl, p-methylphenyl, methyl, 2,4-difluorophenyl or p-chlorphenyl; and R2 is p-methoxyphenyl, p-methylphenyl or phenyl. The analogues have equivalent or higher contact toxicity on Tetrangychus cinnabarinus and Aphis craccivora compared with ivermectin, so the analogues can be used for preventing and controlling the agricultural pests (mites).

Description

technical field [0001] The invention belongs to the field of pesticide compounds, and in particular relates to a milbemycin analogue, a preparation method thereof and an application in pesticides. Background technique [0002] Avermectins are a class of sixteen-membered macrolide disaccharide compounds with insecticidal, acaricidal and nematicidal activities first developed by Satoshi Omura of Kitasato University in Japan and Merck in the United States. As an important class of antibiotics, it has become a highly efficient biological source insecticide for agricultural and veterinary use. And ivermectin (ivermectin) is developed by American Merck Company to AVMB l C 22 with C 23 The first abamectin derivative obtained after the double bond reduction hydrogenation treatment between. Compared with abamectin, the insecticidal activity of ivermectin is basically unchanged, but it has stronger penetration and safety to mammalian body tissues, and the duration of effect is lon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/22A01N43/90A01P7/02A01P7/04
CPCA01N43/90C07D493/22
Inventor 胡冠芳刘映前赵晓博余海涛南祥刘敏艳牛树君李玉奇
Owner INST OF PLANT PROTECTION GANSU ACAD OF AGRI SCI
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