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Synthesis method of spiroxamine as bactericide

A synthesis method and spirocycline technology are applied in the field of fungicides synthesis, which can solve the problems of expensive raw materials, difficult purification of intermediates, and inability to produce large-scale production, and achieve high reaction yield, low cost, and mild experimental conditions. Effect

Active Publication Date: 2013-05-29
JIANGSU FLAG CHEM IND
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Problems solved by technology

[0012] The purpose of the present invention is to provide a high-efficiency and low-toxicity fungicide spirocycline in order to solve the technical problems such as high cost of raw materials such as N-ethyl n-propylamine in the existing spirulina preparation process, intermediates are not easy to purify, and cannot be produced on a large scale. The synthetic method of bacteramine

Method used

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  • Synthesis method of spiroxamine as bactericide
  • Synthesis method of spiroxamine as bactericide
  • Synthesis method of spiroxamine as bactericide

Examples

Experimental program
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Effect test

Embodiment 1

[0032] (1) Synthesis of compound N-ethyl-8-tert-butyl-1,4-dioxaspiro[4.5]decane-2-methylamine XI:

[0033]

[0034] 50 grams of {8-tert-butyl-1,4-dioxaspiro[4.5]decane-2-methyl} methanesulfonate X (0.163 mol), 21.9 grams of 67% Ethylamine aqueous solution (0.326 mol) and 24.8 grams of potassium carbonate (0.179 mol), then heated to 110-115 ° C, the internal pressure is 0.4MPa stirring reaction after 24 hours, the reaction mixture was distilled to remove ethanol and excess ethylamine aqueous solution recovery, The residue was added with 700 ml of dichloroethane and 300 ml of water, stirred and dissolved, and allowed to stand for stratification. The organic layer was concentrated under reduced pressure to obtain 39.5 g of brown liquid N-ethyl-8-tert-butyl-1,4-dioxaspiro [4.5] Decane-2-methylamine XI, yield 94.9%. 1 H NMR (400MHz, CDCl3) δ (ppm) 4.20-4.30 (m, 1H), 4.00-4.10 (m, 1H), 3.6-3.7 (m, 1H), 2.60-2.80 (m, 4H), 1.80-1.90 (m,1H),1.70-1.80(m,3H),1.60(m,1H),1.2-1.5(m,3H)...

Embodiment 2

[0039] (1) Synthesis of compound N-propyl-8-tert-butyl-1,4-dioxaspiro[4.5]decane-2-methylamine XII:

[0040]

[0041] In a 500 ml autoclave, 25.0 g of {8-tert-butyl-1,4-dioxaspiro[4.5]decane-2-methyl} ester X (81.6 mmol) and 9.65 g of n- Propylamine (163.2 mmol), 12.4 grams of potassium carbonate (89.76 mmol) and 150 milliliters of ethanol, the reaction mixture was heated to 110-115 ° C and the internal pressure was 0.5 MPa, reacted under stirring for 24 hours and then cooled to room temperature, the reaction mixture was distilled off Ethanol and excess propylamine were recovered and applied mechanically. The residue was added with 500 ml of dichloroethane and 200 ml of water, stirred and dissolved, and left to stand for layering. The organic layer was concentrated under reduced pressure to obtain 17.6 g of brown oil N-propyl-8-tert-butyl -1,4-dioxaspiro[4.5]decane-2-methylamine XII, the yield is 80%. 1H NMR (400MHz, CDCl3) δ (ppm) 4.20-4.30 (m, 1H), 4.01-4.06 (m, 1H), 3.6...

Embodiment 3

[0046] (1) Synthesis of compound N-propyl-8-tert-butyl-1,4-dioxaspiro[4.5]decane-2-methylamine XII

[0047]

[0048] 31.2 grams of p-toluenesulfonic acid {8-tert-butyl-1,4-dioxaspiro[4.5]decane-2-methyl} ester X' (81.59 mmol), 14.47 grams n-Propylamine (244.76 mmol), 12.4 g of potassium carbonate (89.75 mmol) and 150 ml of ethanol were heated in an autoclave to 118-120 °C with an internal pressure of 0.7 MPa. After stirring for 24 hours, concentrate under reduced pressure to recover ethanol and excess isopropylamine, add 700 milliliters of dichloroethane and 500 milliliters of water to the residue, stir and stand for stratification, and concentrate the organic phase under reduced pressure to obtain 21 grams of N-propyl-8-tert-butyl-1,4 -Dioxaspiro[4.5]decane-2-methylamine XII, yield: 95.5%. 1 H NMR (400MHz, CDCl3) δ (ppm) 4.20-4.30 (m, 1H), 4.01-4.06 (m, 1H), 3.65-3.67 (m, 1H), 2.70-2.74 (m, 2H), 2.57-2.63 (q,2H),1.10-1.90(m,10H),1.00(m,1H),0.90(m,3H),0.80-0.90(m,9H).

...

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Abstract

The invention discloses a synthesis method of spiroxamine as a bactericide. The synthesis method comprises the following steps of: (1) subjecting a compound X and alkylamine to a reaction under the action of alkali to obtain a compound XI; and (2) subjecting the compound XI, alkyl bromide and alkali to a reaction under the action of a phase transfer catalyst to obtain a compound I, wherein R1 is an alkyl group selected from C1 to C4 or an alkyl phenyl selected from C1 to C4, and R2 is n-propyl or ethyl. The synthesis method is low in cost, simple and convenient for reaction operation, mild in experiment condition, little in pollution, high in reaction yield in each step and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of fungicide synthesis, and in particular relates to a new method for synthesizing the fungicide spirulina. Background technique [0002] Spiroxamine, also known as spirooxamine, spirooxamine, N-ethyl-N-propyl-8-tert-butyl-1,4-dioxaspiro[4.5]decane-2-methylamine , its English name Spiroxamine, English alias N-Ethyl-N-propyl-8-tert-butyl-1, 4-dioxaspiro[4.5]dec-2-ylmethylamine, its CAS NO.118134-30-8, molecular formula C 18 h 35 NO 2 , molecular weight 297.48. [0003] Mechanism and characteristics of spirulina: sterol biosynthesis inhibitor, mainly inhibits the synthesis of C-14 demethylase. Application: suitable crop and safety wheat and barley. The recommended dosage is safe and harmless to crops. The control objects are wheat powdery mildew and various rusts, barley moire and stripe disease. Spirulina is a novel, systemic foliar fungicide that is particularly effective against powdery mildew. It acts quickl...

Claims

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Application Information

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IPC IPC(8): C07D317/72
Inventor 王凤云剧宗峰赵祝槽吴耀军
Owner JIANGSU FLAG CHEM IND
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