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Preparation and plant growth-regulating activity of water-oil soluble o-(4-chloro) benzylthio-benzoate derivatives

A technology of benzylthiobenzoic acid and its derivatives, which is applied in the field of preparation of o-(4-chloro)benzylthiobenzoic acid ester derivatives that are compatible with water and oil and in the field of plant growth regulation activity, so as to promote plant growth, Good plant growth regulating activity, good water solubility and oil solubility effect

Inactive Publication Date: 2012-10-17
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Very hydrophilic drugs cannot pass through the lipid layer of the biomembrane, while very hydrophobic drugs remain as part of the biomembrane for similar and compatible reasons, so they cannot effectively enter the inner cytoplasm

Method used

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  • Preparation and plant growth-regulating activity of water-oil soluble o-(4-chloro) benzylthio-benzoate derivatives
  • Preparation and plant growth-regulating activity of water-oil soluble o-(4-chloro) benzylthio-benzoate derivatives
  • Preparation and plant growth-regulating activity of water-oil soluble o-(4-chloro) benzylthio-benzoate derivatives

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Embodiment Construction

[0055] The following examples and bioassay results can be used to further illustrate the plant growth regulating activity of the compounds of the present invention, but are not meant to limit the present invention.

[0056] Synthetic example

[0057] Compound 1: Synthesis of ethyl 2'-N,N-dimethyl-2-(4-chloro)benzylthiobenzoate

[0058] In a 100mL round bottom flask, add 2.785g (0.01mol) of o-(4-chloro) benzylthiobenzoic acid and 10ml of thionyl chloride, then heat to reflux for 8h, cool, and distill off excess thionyl chloride under reduced pressure , to obtain o-(4-chloro)benzylthiobenzoyl chloride as a brown-gray solid.

[0059] In the above-mentioned 100mL round-bottomed flask filled with 0.01mol of the prepared acid chloride, add 20mL of dichloromethane to dissolve the acid chloride, then slowly add 0.89g of N,N-dimethylethanolamine, 1.5mL of triethyl The mixed solution of amine and 15ml of dichloromethane was added dropwise, stirred at room temperature overnight, TLC de...

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Abstract

The invention provides water-oil soluble o-(4-chloro) benzylthio-benzoate derivatives with plant growth-regulating activity and salts thereof. The derivatives are shown as a general formula (I, II), wherein X is an oxygen atom, a nitrogen atom or a sulfur atom; n is 0, 1, 2, 3, 4, 5 and so on or (CH2)n represents alkyl carrying a branched chain; Y is Cl<->, Br<->, F<->, I<->, AcO<->, acetylsalicylic acid radical, nitric acid radical, salicylic acid radical, p-toluenesulfonic acid radical, bisulfate radical or other negative ions; R<1> is alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, alkenyl of 1-6 carbon atoms, or aryl; R<2> is alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, alkenyl of 1-6 atoms, or aryl; or R<1> and R<2> are selected from the structure in the specification.

Description

technical field [0001] The invention relates to the preparation and plant growth regulating activity of a novel o-(4-chloro)benzylthiobenzoate derivative which is compatible with water and oil. Background technique [0002] The research on plant growth regulating substances began with the discovery of auxin in 1928. 1934 Identified the first natural hormone 3-indoleacetic acid (IAA), and found that it can promote the elongation of plant stem cells and promote the rooting of cuttings, and later found that some compounds also have obvious plant physiological regulation, and then define plant growth Regulators are substances that affect plant growth without causing plant death. Plant growth regulating substances can be divided into two types: endogenous and exogenous. The former are generally called plant hormones, and the latter are called plant growth regulators. They are artificially synthesized chemical substances. They do not necessarily exist in plants, but they are I...

Claims

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Application Information

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IPC IPC(8): C07C323/62C07C319/20C07D295/088A01N37/40A01P21/00
Inventor 邹小毛吴建国王瑞花丁会娟刘殿甲傅翠蓉杨华铮李伟臧福坤刘俊单鹏程黄纯陈森
Owner NANKAI UNIV
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