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1-cycloalkyl-5-iodotetrazoles

A compound and cycloalkyl technology, applied in organic chemistry, drug combination, animal repellent, etc., can solve problems that do not mention biological effects

Inactive Publication Date: 2008-07-09
LANXESS DEUTDCHLAND GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Biological effects are not mentioned in any of the prior art examples

Method used

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  • 1-cycloalkyl-5-iodotetrazoles
  • 1-cycloalkyl-5-iodotetrazoles
  • 1-cycloalkyl-5-iodotetrazoles

Examples

Experimental program
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Effect test

example 1

[0205] 1-cyclopentyl-5-iodotetrazole

[0206] In an inert gas environment, 10.42 mmol of butyllithium (1.6 M hexane solution ), so that the temperature of the reaction mixture does not exceed -70°C. The mixture was stirred at this temperature for 30 minutes, then 4 ml of a solution of 8.68 mmol (2.2 g) of iodine in anhydrous tetrahydrofuran were added dropwise. After stirring at this temperature for 30 minutes, the reaction mixture was heated to 23°C and water was added carefully. The solvent was extracted with ethyl acetate and the combined organic phases were washed with sodium thiosulfate solution and saturated sodium chloride solution and dried over sodium sulfate. The solid obtained by distilling off the solvent under reduced pressure was stirred with diisopropyl ether to obtain 1.55 g (68%) of 1-cyclopentanol-5-iodotetrazole having a melting point of 119°C.

[0207] The preparation method of the compound listed in table 1 is similar to example 1:

[0208]

[0209]...

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Abstract

Disclosed are compounds of formula (I), wherein R<1> represents cycloalkyl, and the stereoisomers and any mixtures thereof. Said compounds are excellent microbicides used for protecting plants and materials.

Description

technical field [0001] The present invention relates to novel 1-cycloalkyl-5-iodotetrazoles, to processes for their preparation and to their use as biocides for the protection of plants and industrial materials. Background technique [0002] Some 5-iodotetrazoles and routes to their preparation are known from the literature. Its biological role is not mentioned in any of the prior art examples. 1-Cycloalkyl-5-iodotetrazoles are unknown in the literature. [0003] 5-iodotetrazoles can be obtained by reacting 1-substituted 5-tetrazolyl lithium compounds with iodine at low temperature (cf.R.Raap, Can.J.Chem.1971,49,2139; Satoh, Yoshitaka; Tetrahedron Lett. 1995, 36, 1759; Satoh, Yoshitaka, Synlett 1998, 528). [0004] Another way to prepare 1-alkyl-5-iodotetrazoles is to use 1-alkyltetrazoles as starting materials and place them in the presence of KMnO 4 and H 2 SO 4 Treatment with iodine in glacial acetic acid (cf. P.N. Gaponik, Khimiya Geterotsiklicheskikh Soedinenii 19...

Claims

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Application Information

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IPC IPC(8): C07D257/04A01N43/713
CPCC07D257/04A61P31/00A01N43/713
Inventor 赖纳·布伦斯马丁·库格勒伊拉斯谟·福格尔赫尔曼·乌尔奥利弗·克雷奇克
Owner LANXESS DEUTDCHLAND GMBH
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