{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1390282680187938432.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1584/jpestics.g11-28"}},{"identifier":{"@type":"URI","@value":"http://www.jstage.jst.go.jp/article/jpestics/36/3/36_G11-28/_pdf"}},{"identifier":{"@type":"NAID","@value":"130004939661"}}],"dc:title":[{"@language":"en","@value":"Synthesis and insecticidal activity of 1,2,4-oxadiazole and 1,2,4-thiadiazole derivatives"}],"dc:language":"en","description":[{"type":"abstract","notation":[{"@language":"en","@value":"A series of 5-substituted 1,2,4-oxadiazoles and 1,2,4-thiadiazoles were prepared as muscarinic acetylcholine receptor agonists and evaluated for their insecticidal activity. These derivatives were synthesized through sequential reactions consisting of the condensation of pyridinecarboamides or pyridinecarbothioamides with <i>N</i>,<i>N</i>-dimethylacetamide dimethyl acetal, cyclization with hydroxylamine, quaternization by alkyl halide and reaction with sodium borohydride. All 1,2,4-oxadiazoles and 1,2,4-thiadiazoles synthesized were evaluated for insecticidal activity and their structure-activity relationships are discussed. It was discovered that many compounds were active against representative insects such as <i>Nilaparvata lugens</i>, <i>Nephotettix cincticeps</i> and <i>Aphis craccivora</i>. In particular, it was also found that 3-pyridyl-substituted derivatives of 1,2,4-oxadiazole and 1,2,4-thiadiazole exhibited good insecticidal activity against all the insects tested. Among the compounds evaluated, 3-methyl-5-(1,2,5,6-tetrahydropyridin-3-yl)-1,2,4-thiadiazole (<b>9m-2</b>) showed the highest activity against <i>Nilaparvata lugens</i>, and provided a high level of activity against the imidacloprid-resistant strain. Based on the preliminary binding assay using the binding inhibition of mAChR antagonist [<sup>3</sup>H]NMS to the nerve-cord membranes as an index of the binding activity, <b>9m-2</b> exhibited a range of potencies for the insect muscarinic receptor."}],"abstractLicenseFlag":"disallow"}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1410282680187938436","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000283588635"}],"foaf:name":[{"@language":"en","@value":"Suzuki Jun"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Hokko Chemical Industry Co., Ltd."}]},{"@id":"https://cir.nii.ac.jp/crid/1410282680187938435","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000283588636"}],"foaf:name":[{"@language":"en","@value":"Okamura Daigo"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Hokko Chemical Industry Co., Ltd."}]},{"@id":"https://cir.nii.ac.jp/crid/1410282680187938432","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000283588637"}],"foaf:name":[{"@language":"en","@value":"Gushikawa Toru"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Hokko Chemical Industry Co., Ltd."}]},{"@id":"https://cir.nii.ac.jp/crid/1410282680187938434","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000283588638"}],"foaf:name":[{"@language":"en","@value":"Hirai Kenji"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Sagami Chemical Research 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Tetsu"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Graduate School of Bio-applications and Systems Engineering (BASE), Tokyo University of Agriculture and Technology"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"1348589X"},{"@type":"EISSN","@value":"13490923"},{"@type":"CODEN","@value":"JPSTCF"}],"prism:publicationName":[{"@language":"en","@value":"Journal of Pesticide Science"},{"@language":"ja","@value":"日本農薬学会誌（Ｊｏｕｒｎａｌ　ｏｆ　Ｐｅｓｔｉｃｉｄｅ　Ｓｃｉｅｎｃｅ）"},{"@language":"en","@value":"J. Pestic. Sci."},{"@language":"en","@value":"Journal of Pesticide Science"},{"@language":"ja","@value":"日本農薬学会誌（Ｊｏｕｒｎａｌ　ｏｆ　Ｐｅｓｔｉｃｉｄｅ　Ｓｃｉｅｎｃｅ）"}],"dc:publisher":[{"@language":"en","@value":"Pesticide Science Society of Japan"},{"@language":"ja","@value":"日本農薬学会"}],"prism:publicationDate":"2011","prism:volume":"36","prism:number":"3","prism:startingPage":"392","prism:endingPage":"401"},"reviewed":"false","dcterms:accessRights":"http://purl.org/coar/access_right/c_abf2","url":[{"@id":"http://www.jstage.jst.go.jp/article/jpestics/36/3/36_G11-28/_pdf"}],"availableAt":"2011","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=oxadiazole","dc:title":"oxadiazole"},{"@id":"https://cir.nii.ac.jp/all?q=thiadiazole","dc:title":"thiadiazole"},{"@id":"https://cir.nii.ac.jp/all?q=tetrahydropyridine","dc:title":"tetrahydropyridine"},{"@id":"https://cir.nii.ac.jp/all?q=insecticidal%20activity","dc:title":"insecticidal activity"},{"@id":"https://cir.nii.ac.jp/all?q=muscarinic%20acetylcholine%20receptor","dc:title":"muscarinic acetylcholine receptor"}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1360574094999669248","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Neonicotinoids: insecticides acting on insect nicotinic acetylcholine receptors"}]},{"@id":"https://cir.nii.ac.jp/crid/1360574095387529856","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Pharmacological profiles of recombinant and native insect nicotinic acetylcholine receptors"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137043700178048","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"On the Role of Electrophilic Catalysis in Competitive Reductions of Ketones by Lithium Tetrakis(N-dihydropyridyl)aluminate and Metal Borohydrides"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137044886168320","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"New synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137045627867904","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Quinuclidinyl Benzilate Binding in House Fly Heads and Rat Brain"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137046077402624","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Loss of M2 Muscarine Receptors in the Cerebral Cortex in Alzheimer's Disease and Experimental Cholinergic Denervation"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137046131868672","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Nicotinoid Insecticides and the Nicotinic Acetylcholine Receptor"}]},{"@id":"https://cir.nii.ac.jp/crid/1361137046309107968","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Physostigmine and Arecoline: Effects of Intravenous Infusions in Alzheimer Presenile Dementia"}]},{"@id":"https://cir.nii.ac.jp/crid/1363107369419900032","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Role of neurotransmission in the regulation of amyloid β-protein precursor processing"}]},{"@id":"https://cir.nii.ac.jp/crid/1363388844213462656","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Benzylidene anabaseines act as high-affinity agonists for insect nicotinic acetylcholine receptors"}]},{"@id":"https://cir.nii.ac.jp/crid/1363388845237307008","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"New synthesis of 1,2,4-thiadiazoles"}]},{"@id":"https://cir.nii.ac.jp/crid/1364233269922140672","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Picrodendrin and related terpenoid antagonists reveal structural differences between ionotropic GABA receptors of mammals and insects"}]},{"@id":"https://cir.nii.ac.jp/crid/1364233270394970880","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@value":"Novel functional M1 selective muscarinic agonists. Synthesis and structure-activity relationships of 3-(1,2,5-thiadiazolyl)-1,2,5,6-tetrahydro-1-methylpyridines"}]},{"@id":"https://cir.nii.ac.jp/crid/1390282680187472896","@type":"Article","relationType":["references"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Molecular Mechanism for Selective Toxicity of Nicotinoids and Neonicotinoids"},{"@language":"ja","@value":"ニコチノイドおよびネオニコチノイドの選択毒性の分子機構"},{"@value":"ニコチノイドおよびネオニコチノイドの選択毒性の分子機構〔英文〕"},{"@language":"ja-Kana","@value":"ニコチノイド オヨビ ネオニコチノイド ノ センタク ドクセイ ノ ブンシ キ"}]}],"dataSourceIdentifier":[{"@type":"JALC","@value":"oai:japanlinkcenter.org:0037554864"},{"@type":"CROSSREF","@value":"10.1584/jpestics.g11-28"},{"@type":"CIA","@value":"130004939661"},{"@type":"OPENAIRE","@value":"doi_dedup___::2f16038053865f8c77f0803f2e528126"}]}