CN113527152A - 一种联苯磺酰胺类化合物及其防治农作物害虫的方法 - Google Patents
一种联苯磺酰胺类化合物及其防治农作物害虫的方法 Download PDFInfo
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- CN113527152A CN113527152A CN202110909199.XA CN202110909199A CN113527152A CN 113527152 A CN113527152 A CN 113527152A CN 202110909199 A CN202110909199 A CN 202110909199A CN 113527152 A CN113527152 A CN 113527152A
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- biphenylsulfonamide
- methyl
- sulfonamide
- propargyloxy
- acetonitrile
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- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims (10)
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4514213A (en) * | 1984-03-19 | 1985-04-30 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
CN1212255A (zh) * | 1997-09-22 | 1999-03-31 | 德国赫彻斯特马里奥罗塞尔有限公司 | 联苯磺酰基氨基氰、其制备方法及其作为药物的用途 |
CN1623537A (zh) * | 2003-12-04 | 2005-06-08 | 惠氏公司 | 联芳基磺酰胺及其使用方法 |
CN101141878A (zh) * | 2005-03-16 | 2008-03-12 | 巴斯福股份公司 | 联苯-n-(4-吡啶基)甲基磺酰胺 |
US20080063678A1 (en) * | 2004-11-26 | 2008-03-13 | Basf Aktiengesellschaft | Novel 2-Cyano-3(Halo)Alkoxy-Benzenesulfonamide Compounds for Combating Animal Pests |
CN101657471A (zh) * | 2006-12-06 | 2010-02-24 | 史密丝克莱恩比彻姆公司 | 二环化合物及其作为抗糖尿病药的用途 |
CN106008288A (zh) * | 2016-06-15 | 2016-10-12 | 西北农林科技大学 | 一种苯磺酰胺类化合物及其用途 |
-
2021
- 2021-08-09 CN CN202110909199.XA patent/CN113527152B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4514213A (en) * | 1984-03-19 | 1985-04-30 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
CN1212255A (zh) * | 1997-09-22 | 1999-03-31 | 德国赫彻斯特马里奥罗塞尔有限公司 | 联苯磺酰基氨基氰、其制备方法及其作为药物的用途 |
CN1623537A (zh) * | 2003-12-04 | 2005-06-08 | 惠氏公司 | 联芳基磺酰胺及其使用方法 |
US20080063678A1 (en) * | 2004-11-26 | 2008-03-13 | Basf Aktiengesellschaft | Novel 2-Cyano-3(Halo)Alkoxy-Benzenesulfonamide Compounds for Combating Animal Pests |
CN101141878A (zh) * | 2005-03-16 | 2008-03-12 | 巴斯福股份公司 | 联苯-n-(4-吡啶基)甲基磺酰胺 |
CN101657471A (zh) * | 2006-12-06 | 2010-02-24 | 史密丝克莱恩比彻姆公司 | 二环化合物及其作为抗糖尿病药的用途 |
CN106008288A (zh) * | 2016-06-15 | 2016-10-12 | 西北农林科技大学 | 一种苯磺酰胺类化合物及其用途 |
Non-Patent Citations (7)
Title |
---|
CHAOFU YANG等: "Synthesis and evaluation of 4-(1,3,4-oxadiazol-2-yl)-benzenesulfonamides as potent carbonic anhydrase inhibitors", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
CHAOFU YANG等: "Synthesis and insecticidal activity in vitro and vivo of novel benzenesulfonyl derivatives based on potent target subunit H of V-ATPase", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
FANGLI GANG等: "Synthesis and Insecticidal Activity Evaluation of Virtually Screened Phenylsulfonamides", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
IAIN R. GREIG等: "Development and Characterization of Biphenylsulfonamides as Novel Inhibitors of Bone Resorption", 《JOURNAL OF MEDICINAL CHEMISTRY》 * |
WANG-YU ZHAO等: "Design, synthesis, and insecticidal activities of propargyloxy-naphthalene-sulfonamide derivatives", 《JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH》 * |
李晓婷: "苯磺酰胺类化合物合成及其杀虫活性", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
李能刚等: "4′-甲基-N-叔丁基-1′,2-联苯磺酰胺的合成", 《中国医药工业杂志》 * |
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Effective date of registration: 20240429 Address after: 714100 Guapo Fine Chemical Zone, Industrial Park, Huazhou District, Weinan City, Shaanxi Province (south side of National Highway 310) Patentee after: SHAANXI KONHO LIFENG BIOTECHNOLOGY PHARMACEUTICAL CO.,LTD. Country or region after: China Address before: 712100 Xianyang city of Shaanxi province Yangling Demonstration Zone No. 3 Tai Road Patentee before: NORTHWEST A & F University Country or region before: China |