Synthesis and fungicidal activity of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines

[Display omitted] A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino)methyl)phenols or 4-methyl-2-((1,3,4-thiadiazolylamino)methyl)phenols and 2- or 4-nitrobenzaldehyde in the presence of TMSCl in refluxing to...

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Published inBioorganic & medicinal chemistry letters Vol. 25; no. 16; pp. 3378 - 3381
Main Authors Tang, Zi-long, Xia, Zan-wen, Chang, Shu-hong, Wang, Zhao-xu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.08.2015
Elsevier
Subjects
(13,4-Thiadiazolyl)-1,3-benzoxazines
Benzoxazines - chemical synthesis
Benzoxazines - chemistry
Benzoxazines - pharmacology
Botrytis - drug effects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Fungicidal activity
Fungicides, Industrial - chemical synthesis
Fungicides, Industrial - chemistry
Fungicides, Industrial - pharmacology
Life Sciences & Biomedicine
Molecular Structure
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
Synthesis
TMSCl
TMSCl
Synthesis
(13,4-Thiadiazolyl)-1,3-benzoxazines
Fungicidal activity
BIOLOGICAL-ACTIVITY
ALDEHYDES
DERIVATIVES
DISCOVERY
Online AccessGet full text
ISSN0960-894X
1464-3405
1464-3405
DOI10.1016/j.bmcl.2015.05.010

Cover

Abstract [Display omitted] A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino)methyl)phenols or 4-methyl-2-((1,3,4-thiadiazolylamino)methyl)phenols and 2- or 4-nitrobenzaldehyde in the presence of TMSCl in refluxing toluene. The electron-donating methyl group on the benzene ring played an essential role on the reactivity of the substituted phenols, which was proved by DFT calculation. The fungicidal activity of the resultant products were also preliminarily evaluated, most of which displayed moderate to good fungicidal activity. Especially, compound 6f showed 98.0% activity against Sclerotonia sclerotiorum and Botrytis cinerea at concentration of 25μg/mL.
AbstractList A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino)methyl)phenols or 4-methyl-2-((1,3,4-thiadiazolylamino)methyl)phenols and 2- or 4-nitrobenzaldehyde in the presence of TMSCl in refluxing toluene. The electron-donating methyl group on the benzene ring played an essential role on the reactivity of the substituted phenols, which was proved by DFT calculation. The fungicidal activity of the resultant products were also preliminarily evaluated, most of which displayed moderate to good fungicidal activity. Especially, compound 6f showed 98.0% activity against Sclerotonia sclerotiorum and Botrytis cinerea at concentration of 25μg/mL.A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino)methyl)phenols or 4-methyl-2-((1,3,4-thiadiazolylamino)methyl)phenols and 2- or 4-nitrobenzaldehyde in the presence of TMSCl in refluxing toluene. The electron-donating methyl group on the benzene ring played an essential role on the reactivity of the substituted phenols, which was proved by DFT calculation. The fungicidal activity of the resultant products were also preliminarily evaluated, most of which displayed moderate to good fungicidal activity. Especially, compound 6f showed 98.0% activity against Sclerotonia sclerotiorum and Botrytis cinerea at concentration of 25μg/mL.
A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino)methyl)phenols or 4-methyl-2-((1,3,4-thiadiazolylamino)methyl)phenols and 2- or 4-nitrobenzaldehyde in the presence of TMSCl in refluxing toluene. The electron-donating methyl group on the benzene ring played an essential role on the reactivity of the substituted phenols, which was proved by DFT calculation. The fungicidal activity of the resultant products were also preliminarily evaluated, most of which displayed moderate to good fungicidal activity. Especially, compound 6f showed 98.0% activity against Sclerotonia sclerotiorum and Botrytis cinerea at concentration of 25μg/mL.
A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino) methyl) phenols or 4-methyl-2-((1,3,4-thiadiazolylamino) methyl)phenols and 2- or 4-nitrobenzaldehyde in the presence of TMSCl in refluxing toluene. The electron-donating methyl group on the benzene ring played an essential role on the reactivity of the substituted phenols, which was proved by DFT calculation. The fungicidal activity of the resultant products were also preliminarily evaluated, most of which displayed moderate to good fungicidal activity. Especially, compound 6f showed 98.0% activity against Sclerotonia sclerotiorum and Botrytis cinerea at concentration of 25 mu g/mL. (C) 2015 Elsevier Ltd. All rights reserved.
[Display omitted] A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino)methyl)phenols or 4-methyl-2-((1,3,4-thiadiazolylamino)methyl)phenols and 2- or 4-nitrobenzaldehyde in the presence of TMSCl in refluxing toluene. The electron-donating methyl group on the benzene ring played an essential role on the reactivity of the substituted phenols, which was proved by DFT calculation. The fungicidal activity of the resultant products were also preliminarily evaluated, most of which displayed moderate to good fungicidal activity. Especially, compound 6f showed 98.0% activity against Sclerotonia sclerotiorum and Botrytis cinerea at concentration of 25μg/mL.
Author Chang, Shu-hong
Tang, Zi-long
Xia, Zan-wen
Wang, Zhao-xu
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Keywords TMSCl
Synthesis
(13,4-Thiadiazolyl)-1,3-benzoxazines
Fungicidal activity
BIOLOGICAL-ACTIVITY
ALDEHYDES
DERIVATIVES
DISCOVERY
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  doi: 10.1021/ml900009d
SSID ssj0014044
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Snippet [Display omitted] A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of...
A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino) methyl) phenols...
A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino)methyl)phenols or...
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SubjectTerms (13,4-Thiadiazolyl)-1,3-benzoxazines
Benzoxazines - chemical synthesis
Benzoxazines - chemistry
Benzoxazines - pharmacology
Botrytis - drug effects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Fungicidal activity
Fungicides, Industrial - chemical synthesis
Fungicides, Industrial - chemistry
Fungicides, Industrial - pharmacology
Life Sciences & Biomedicine
Molecular Structure
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
Synthesis
TMSCl
Title Synthesis and fungicidal activity of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines
URI https://dx.doi.org/10.1016/j.bmcl.2015.05.010
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https://www.ncbi.nlm.nih.gov/pubmed/26071637
https://www.proquest.com/docview/1694706719
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