CA2869634C - Biocidal compounds and methods for using same - Google Patents

Biocidal compounds and methods for using same Download PDF

Info

Publication number
CA2869634C
CA2869634C CA2869634A CA2869634A CA2869634C CA 2869634 C CA2869634 C CA 2869634C CA 2869634 A CA2869634 A CA 2869634A CA 2869634 A CA2869634 A CA 2869634A CA 2869634 C CA2869634 C CA 2869634C
Authority
CA
Canada
Prior art keywords
alkyl
independently
taken together
together form
halamine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2869634A
Other languages
English (en)
French (fr)
Other versions
CA2869634A1 (en
Inventor
Song Liu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Manitoba
Original Assignee
Exigence Technologies Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Exigence Technologies Inc filed Critical Exigence Technologies Inc
Publication of CA2869634A1 publication Critical patent/CA2869634A1/en
Application granted granted Critical
Publication of CA2869634C publication Critical patent/CA2869634C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
    • C07D233/82—Halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/30—Woven fabric [i.e., woven strand or strip material]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/40—Knit fabric [i.e., knit strand or strip material]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Oncology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2869634A 2012-05-17 2013-05-16 Biocidal compounds and methods for using same Active CA2869634C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201261648167P 2012-05-17 2012-05-17
US61/648,167 2012-05-17
US201361772440P 2013-03-04 2013-03-04
US61/772,440 2013-03-04
PCT/CA2013/000491 WO2013173905A1 (en) 2012-05-17 2013-05-16 Biocidal compounds and methods for using same

Publications (2)

Publication Number Publication Date
CA2869634A1 CA2869634A1 (en) 2013-11-28
CA2869634C true CA2869634C (en) 2018-11-27

Family

ID=49622958

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2869634A Active CA2869634C (en) 2012-05-17 2013-05-16 Biocidal compounds and methods for using same

Country Status (9)

Country Link
US (4) US20150118179A1 (https=)
EP (2) EP3357920A1 (https=)
JP (2) JP2015523331A (https=)
CN (1) CN104968655A (https=)
AU (1) AU2013265971A1 (https=)
CA (1) CA2869634C (https=)
IN (1) IN2014DN09443A (https=)
MX (1) MX2014013991A (https=)
WO (1) WO2013173905A1 (https=)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2880639A1 (en) * 2012-08-01 2014-02-06 The Hospital For Sick Children Inhibitors of peptidyl arginine deiminase (pad) enzymes and uses thereof
CN104910208B (zh) * 2015-05-15 2017-07-21 大连理工大学 季膦盐型卤胺抗菌剂及其制备方法
CN104926787A (zh) * 2015-05-15 2015-09-23 大连理工大学 吡啶季铵盐型卤胺抗菌剂及其制备方法
CA3001921C (en) 2015-10-16 2021-04-27 Exigence Technologies Inc. Compounds, polymers and coating formulations that comprise at least one n-halamine precursor, a cationic center and a coating incorporation group
WO2017079825A1 (en) * 2015-11-13 2017-05-18 Exigence Technologies Inc. Monomers, polymers and coating formulations that comprise at least one n-halamine precursor, a cationic center and a coating incorporation group
CN105613506B (zh) * 2016-03-22 2018-06-19 江南大学 一种卤胺/季铵烯烃类抗菌剂及其在生物可降解纳米纤维材料中的应用
WO2017197518A1 (en) * 2016-05-18 2017-11-23 Exigence Technologies Inc. Compounds with one or more functional groups and use thereof in liquid disinfectants
US10882822B2 (en) 2016-07-06 2021-01-05 University Of Manitoba Use of compounds for making products with at least one N-halamine precursor group and at least one cationic center
CN106359383A (zh) * 2016-08-08 2017-02-01 山东科技大学 一种含双键、季铵盐和卤胺双官能杀菌剂及其制备方法和应用
US20190364895A1 (en) * 2016-09-13 2019-12-05 Exigence Technologies Inc. Antimicrobial compounds or precursors thereof comrpising one or more cationic centers and a coating-incorporation group
CN107778248B (zh) * 2017-11-17 2019-08-20 大连理工大学 双季铵盐型氯胺抗菌剂及其的合成方法
US10611986B1 (en) 2018-03-15 2020-04-07 Earthcare Labs, Llc Cleaning composition comprising a cationic/nonionic mixture
CN108378039B (zh) * 2018-04-18 2020-08-25 大连理工大学 甜菜碱型氯胺抗菌剂及其合成方法
WO2019200478A1 (en) * 2018-04-20 2019-10-24 Exigence Technologies Inc. Use of compounds for making products with at least one n-halamine precursor group and at least one cationic center
CN108752279A (zh) * 2018-07-18 2018-11-06 大连理工大学 一种锍盐型氯胺抗菌剂及其合成方法
CN110372533B (zh) * 2019-07-20 2021-06-15 大连理工大学 一种阳离子型线性氯胺抗菌剂及其合成方法
CN116041266B (zh) * 2022-12-30 2025-07-15 浙江大学绍兴研究院 一种序列可编码聚离子液体的合成方法

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2787619A (en) * 1955-04-08 1957-04-02 Rohm & Haas Method of producing nu-vinyl-nu, nu'-ethyleneurea
US2840546A (en) * 1956-01-06 1958-06-24 Rohm & Haas Unsaturated quaternary ammonium compounds and polymers
US4073924A (en) * 1976-10-04 1978-02-14 Glyco Chemicals, Inc. Hydantoin derivatives and broad spectrum bactericidal/fungicidal compositions thereof
DE2744353A1 (de) * 1976-10-04 1978-04-13 Glyco Chemicals Inc Hydantoinderivate, verfahren zu ihrer herstellung und ihre verwendung
US4073926A (en) * 1976-10-04 1978-02-14 Glyco Chemicals, Inc. Mono-quaternary ammonium salts of hydantoin and compositions thereof
US4820437A (en) * 1986-09-18 1989-04-11 Lion Corporation Bleaching composition
US5882357A (en) * 1996-09-13 1999-03-16 The Regents Of The University Of California Durable and regenerable microbiocidal textiles
US6768009B1 (en) * 2000-03-24 2004-07-27 The Regents Of The University Of California N-halamine vinyl compounds and their polymeric biocides
US6969769B2 (en) * 2002-06-14 2005-11-29 Vanson Halosource, Inc. N-halamine siloxanes for use in biocidal coatings and materials
US7687072B2 (en) * 2002-10-31 2010-03-30 Auburn University Biocidal particles of methylated polystyrene
MX2007008152A (es) * 2005-01-03 2007-09-12 Univ Texas Metodo para la transformacion de polimeros convencionales y comercialmente importantes en materiales polimericos antimicrobianos durables y recargables.
CA2618732A1 (en) * 2005-08-11 2007-10-25 Auburn University N-halamine/quaternary ammonium polysiloxane copolymers
WO2008156636A1 (en) * 2007-06-12 2008-12-24 Michigan Molecular Institute Antimicrobial coatings for conversion of spores into their bacterial vegetative form for decontamination
JP2011501732A (ja) * 2007-09-19 2011-01-13 ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム 着色剤ベースのｎ−ハラミン組成物並びに製造及び使用の方法
JP5599808B2 (ja) * 2008-11-07 2014-10-01 ノバベイ・ファーマシューティカルズ・インコーポレイテッド 抗菌性ｎ−塩素化組成物
WO2010054009A1 (en) * 2008-11-07 2010-05-14 Novabay Pharmaceuticals, Inc. Antimicrobial oxazolidinone, hydantoin and imidazolidinone compositions
AU2011317223A1 (en) * 2010-10-19 2013-05-23 Novabay Pharmaceuticals, Inc. Antimicrobial polyether and polyol compounds

Also Published As

Publication number Publication date
US20170204085A1 (en) 2017-07-20
CN104968655A (zh) 2015-10-07
EP3357920A1 (en) 2018-08-08
US20180086740A1 (en) 2018-03-29
JP2017178947A (ja) 2017-10-05
JP2015523331A (ja) 2015-08-13
EP2850077A1 (en) 2015-03-25
MX2014013991A (es) 2015-08-06
EP2850077A4 (en) 2015-08-26
WO2013173905A1 (en) 2013-11-28
CA2869634A1 (en) 2013-11-28
AU2013265971A1 (en) 2014-12-18
US20190233401A1 (en) 2019-08-01
IN2014DN09443A (https=) 2015-07-17
US20150118179A1 (en) 2015-04-30

Similar Documents

Publication Publication Date Title
CA2869634C (en) Biocidal compounds and methods for using same
Li et al. New biocide with both N‐Chloramine and quaternary ammonium moieties exerts enhanced bactericidal activity
US6020491A (en) Monomeric and polymeric cyclic amine and N-halamine compounds
Ren et al. N-Halamine-coated cotton for antimicrobial and detoxification applications
CN102786477B (zh) 一种含有季铵盐官能团的羟基卤胺类化合物及其制备方法和应用
US6162452A (en) Surface active N-halamine compounds
Demir et al. Polymeric antimicrobial N-halamine-surface modification of stainless steel
CA3001921C (en) Compounds, polymers and coating formulations that comprise at least one n-halamine precursor, a cationic center and a coating incorporation group
WO2007126775A2 (en) Compositions and methods for making and using acyclic n-halamine-based biocidal polymeric materials and articles
Ning et al. Enhanced antibacterial activity of new “composite” biocides with both N-chloramine and quaternary ammonium moieties
Jiang et al. Antimicrobial silica and sand particles functionalized with an N‐halamine acrylamidesiloxane copolymer
US10939684B2 (en) Preparation of sulfonamide-containing antimicrobials and substrate treating compositions of sulfonamide-containing antimicrobials
Doh et al. Development of a food grade sanitizer delivery system with chlorine loaded gelatin microgels for enhanced binding and inactivation of biofilms
WO2017079825A1 (en) Monomers, polymers and coating formulations that comprise at least one n-halamine precursor, a cationic center and a coating incorporation group
Dickerson et al. Sporicidal/bactericidal textiles via the chlorination of silk
US8535654B2 (en) Disinfecting and detoxifying meta-aramid particles
Kocer Synthesis, structure-bioactivity relationship, and application of antimicrobial materials
Zhao et al. Durability of amide N-chloramine biocides to ethylene oxide sterilization
Kou Preparation and Application of Regenerable N-Halamine Biocidal Materials
He et al. Low Molecular Weight Shuttle Molecules Enhance Polychloramide Antimicrobial Activity
Wu Preparation, bioactivity, and application of novel biocidal materials
Qian A study of N-halamine structures in regenerable antimicrobial textiles
Worley et al. Polymeric Materials for Protection Against Chemical and Biological Contaminants
Ahmed Novel N-Halamine Biocidal Polymers for Water Purification.
Zhu Synthesis and Application of Novel Biocidal Materials

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20141103

H11 Ip right ceased following rejected request for revival

Free format text: ST27 STATUS EVENT CODE: T-6-6-H10-H11-H101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: TIME LIMIT FOR REVERSAL EXPIRED

Effective date: 20241118