2-(1,2,4-triazole-1-methyl)-2-(coumarone-5-radical)-1,3-dioxolane and application thereof

A technology of dioxolane and methyl, which is applied in the application field of fungicides and can solve the problems of high toxicity

Inactive Publication Date: 2013-09-04
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Furanol carbamate pesticides have high activity and are widely used, but they are highly toxic. Therefore, it is necessary to develop alternative products with lower toxicity and better activity to meet market demand

Method used

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  • 2-(1,2,4-triazole-1-methyl)-2-(coumarone-5-radical)-1,3-dioxolane and application thereof
  • 2-(1,2,4-triazole-1-methyl)-2-(coumarone-5-radical)-1,3-dioxolane and application thereof
  • 2-(1,2,4-triazole-1-methyl)-2-(coumarone-5-radical)-1,3-dioxolane and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 2-(1,2,4-triazole-1-methyl)-2-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)- Preparation of 1,3-dioxolane (4a)

[0031]

[0032] 1.50 g (5 mmol) 7-methoxy-5-bromoacetyl-2,2-dimethyl-2,3-dihydrobenzofuran (2a), 0.47 g (7.5 mmol) ethylene glycol, 20 ml toluene and 0.10 g p-toluenesulfonic acid, stirred and refluxed for 2.5 h. After the reaction solution was cooled to room temperature, it was washed with water, and the organic layer was dried with anhydrous sodium sulfate, solvent removal, and column chromatography to obtain a pale yellow liquid 2-bromomethyl-2-(7-methoxy-2,2-dimethyl -2,3-dihydrobenzofuran-5-yl)-1,3-dioxolane (3a), yield 79.3%.

[0033] 0.28 g (4 mmol) of 1,2,4-triazole, 15 ml of DMF, 0.75 g of potassium carbonate, and 0.10 g of tetrabutylammonium bromide were stirred and refluxed for 30 min, and 1.03 g (3 mmol) of 2- Bromomethyl-2-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-1,3-dioxolane(3a) in DMF, After dropping, continue to react ...

Embodiment 2

[0035] 4-Methyl-2-(1,2,4-triazole-1-methyl)-2-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran- Preparation of 5-yl)-1,3-dioxolane (4b)

[0036]

[0037] The experimental operation was the same as in Example 1, and the condensation reaction was 4 hours to obtain light yellow liquid 4-methyl-2-bromomethyl-2-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzene Furan-5-yl)-1,3-dioxolane 3b, yield 81.3%; substitution reaction solvent is DMSO, reaction 10h, beige solid 4-methyl-2-(1,2,4- Triazole-1-methyl)-2-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-1,3-dioxolane 4b , m.p.107.5~108.5℃, yield 71.1%; 1 H NMR (CDCl 3 , 400 MHz), δ: 1.08 (d, J = 6.4 Hz, 3H, CH 3 ), 1.52(s, 6H, 2×CH 3 ), 3.03(s, 2H, furan ring CH 2 ), 3.09 (dd, J = 6.8 Hz, J = 7.6 Hz, 1H, OCH 2 ), 3.91 (dd, J = 6.8 Hz, J = 7.6 Hz, 1H, OCH 2 ), 3.87(s, 3H, OCH 3 ), 4.09~4.14(m, 1H, OCH), 4.47(s, 2H, NCH 2 ), 6.88 (s, 1H, benzene ring 4-H), 6.92 (s, 1H, benzene ring 6-H), 7.95 (s, 1H, triazole ring 5-H), 8.21 (s...

Embodiment 3

[0039] 4-Propyl-2-(1,2,4-triazole-1-methyl)-2-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran- Preparation of 5-yl)-1,3-dioxolane (4c)

[0040]

[0041] The experimental operation is the same as in Example 1, and the condensation reaction takes 4.5 hours to obtain light yellow liquid 4-propyl-2-bromomethyl-2-(7-methoxy-2,2-dimethyl-2,3-dihydro Benzofuran-5-yl)-1,3-dioxolane 3c, yield 80.4%; Substitution reaction 12h, 4-propyl-2-(1,2,4-triazole-1 -methyl)-2-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-1,3-dioxolane (4c), yield rate 38.8%, 1 H NMR (DMSO, 400 MHz), δ: 0.82~1.28 (m, 7H, CH 2 CH 2 CH 3 ), 1.40(s, 6H, 2×CH 3 ), 3.00 (s, 2H, furan ring CH 2 ), 3.08(t, J=7.2 Hz, 1H, OCH 2 ), 3.82(t, J = 7.2Hz, 1H, OCH 2 ), 3.75(s, 3H, OCH 3 ), 3.88~3.91(m, 1H, OCH), 4.51(s, 2H, NCH 2 ), 6.81 (s, 1H, benzene ring 4-H), 6.89 (s, 1H, benzene ring 6-H), 7.92 (s, 1H, triazole ring 5-H), 8.35 (s, 1H, triazole ring Ring 3-H).

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Abstract

The invention relates to 2-(1,2,4-triazole-1-methyl)-2-(coumarone-5-radical)-1,3-dioxolane with a chemical formula I shown in the description, where R is selected from C1-C2 alkyl radical and C3-C4 linear alkyl radical or branched alkyl radical, R1 selected from H and C1-C2 alkyl radical, X selected from chlorine,bromine,iodine, mesyloxy,trifluoro-mesyloxy, benzenesulfonyl oxy radical, and p-toluenesulfonyl oxy radical, and Y selected from hydrogen, C1-C2 alkoxy, C3-C4 linear alkoxy or branched alkoxy, chlorine, bromine, fluorine or iodine. The chemical formula I is prepared from a key intermediate II of a chemical formula II shown in the description; and a compound I can be applied to preparation of bactericide.

Description

technical field [0001] The present invention relates to the preparation and application of new compounds, specifically 2-(1,2,4-triazole-1-methyl)-2-(2-methyl-2,3-dihydrobenzofuran-5- base)-1,3-dioxolane and its application as a fungicide. Background technique [0002] Triazole compounds have broad-spectrum fungicidal activity, and have systemic function, protective and therapeutic effects on triazole fungicides, so they are widely used in the prevention and treatment of various diseases caused by fungi such as Ascomycetes and Basidiomycetes [2] . The marketed ketal pesticides such as propiconazole, etoconazole, oxyconazole, difenoconazole and furantazole have shown good fungicidal activity on different crops. [0003] [0004] Furanol (2,2-dimethyl-2,3-dihydrobenzofuran) derivatives pesticides such as furancarb, carbofuran, carbofuran and carbosulfan have been on the market for a long time Carbamate pesticides; this type of furanol derivatives has broad-spectrum insec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14A01N43/653A01P3/00
Inventor 胡艾希李婉唐建刚欧晓明戴明崇
Owner HUNAN UNIV
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