WO2017176543A1 - Combinaison synergique constituée d'un composé de lénacil et de n-butyl-1,2-benzisothiazolin-3-one pour une protection sous forme de film sec - Google Patents

Combinaison synergique constituée d'un composé de lénacil et de n-butyl-1,2-benzisothiazolin-3-one pour une protection sous forme de film sec Download PDF

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Publication number
WO2017176543A1
WO2017176543A1 PCT/US2017/024953 US2017024953W WO2017176543A1 WO 2017176543 A1 WO2017176543 A1 WO 2017176543A1 US 2017024953 W US2017024953 W US 2017024953W WO 2017176543 A1 WO2017176543 A1 WO 2017176543A1
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WO
WIPO (PCT)
Prior art keywords
lenacil
antimicrobial
bbit
coating composition
dry film
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.)
Ceased
Application number
PCT/US2017/024953
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English (en)
Inventor
Pierre Marie Lenoir
Lukas Thomas Johannes VILLIGER
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.)
Dow Global Technologies LLC
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Dow Global Technologies LLC
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 Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Priority to CN201780018559.9A priority Critical patent/CN108882706A/zh
Priority to BR112018069648A priority patent/BR112018069648A2/pt
Priority to AU2017246163A priority patent/AU2017246163A1/en
Priority to MX2018012041A priority patent/MX2018012041A/es
Priority to EP17716416.7A priority patent/EP3439474A1/fr
Publication of WO2017176543A1 publication Critical patent/WO2017176543A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • This invention relates to combinations of antimicrobial compounds and their uses in dry film protection applications, the combinations having unexpectedly greater activity than would be expected for the use of both of the individual antimicrobial compounds.
  • Antimicrobial compounds are sometimes included in liquid coating compositions that are applied to a substrate and that become dry films. It is desirable that such dry films control surface fungi and algae and that such dry films also present as little adverse effect as possible on health and the environment.
  • synergistic antimicrobial composition Comprising 3-Cyclohexyl-6,7-dihydro-lH-cyclopentapyrimidine-2,4-(3H,5H)-dione hereinafter, "lenacil” (CAS registry number 2164-08-1) and N-Butyl-l,2-benzisothiazolin-3- one, hereinafter "BBIT” (CAS registry number is 4299-07-4).
  • the invention further provides a method of inhibiting the growth of or controlling the growth of microorganisms in a building material, the method comprising the step of adding a synergistic antimicrobial composition comprising lenacil and BBIT; wherein the weight ratio of the BBIT to lenacil is from 1: 10 to 5: 1.
  • the present invention further comprises a coating composition comprising a synergistic antimicrobial composition comprising lenacil and BBIT.
  • the coating composition comprising a synergistic antimicrobial composition comprising lenacil and BBIT.
  • composition of the present invention may also comprise a synergistic antimicrobial composition comprising lenacil and BBIT; wherein the weight ratio of the BBIT to lenacil is from 1 : 10 to 5: 1.
  • the present invention provides a dry film made by a process comprising applying a layer of the coating composition onto a substrate comprising a synergistic antimicrobial composition comprising lenacil and BBIT; wherein the weight ratio of the BBIT to lenacil is from 1: 10 to 5: 1 to a substrate and drying the coating composition or allowing the coating composition to dry.
  • antimicrobial compound refers to a compound capable of inhibiting the growth of or controlling the growth of microorganisms; antimicrobial compounds include bactericides, bacteriostats, fungicides, fungistats, algaecides, algistats, and herbicides depending on the dose level applied, system conditions and the level of microbial control desired.
  • antimicrobial compound as used herein is synonymous with the term “biocide”.
  • microorganism includes, for example, fungi (such as yeast and mold), bacteria and algae.
  • fungi such as yeast and mold
  • bacteria and algae.
  • ppm parts per million by weight (weight/ weight)
  • mL milliliter
  • ATCC American Type Culture Collection.
  • temperatures are in degrees centigrade (°C), and references to percentages are by weight (wt%).
  • Percentages of antimicrobial compounds in the composition of this invention are based on the total weight of active ingredients in the composition, i.e., the antimicrobial compounds themselves, exclusive of any amounts of solvents, carriers, dispersants, stabilizers or other materials which may be present.
  • BBIT N-Butyl-l,2-benzisothiazolin-3-one (CAS registry number
  • ratios are the herein to be "X: l or higher,” it is meant that the ratio is Y: l, where Y is X or greater, and when a ratio is the herein to be “X: 1 or lower,” it is meant that the ratio is Z: 1, where Z is X or less.
  • X: l or higher it is meant that the ratio is Y: l, where Y is X or greater
  • X: 1 or lower it is meant that the ratio is Z: 1, where Z is X or less.
  • Lenacil belongs to the class of uracil herbicides, 3-cyclohexyl-l, 5,6,7- tetrahydrocyclopentapyrimidine-2,4(3H)-dione (C1 3 H1 8 N2O2 ) (CAS registry number 2164-08- 1).
  • Lenacil is a known herbicide that is approved in many jurisdictions as a soil-acting herbicide for the control of grass and broad-leaved weeds in beet and other crops.
  • Lenacil has relatively low solubility in water. This relatively low solubility in water is preferred for an antimicrobial material that may be included in a coating composition or other building material, because dried coatings and building materials are exposed to water, which could tend to remove a highly soluble compound from the dried coating or the building material.
  • the present invention involves a composition that contains both lenacil and BBIT. It has been surprisingly found that such a composition is synergistically effective as a biocide. It has been especially surprisingly found that compositions that contain both lenacil and BBIT are synergistically effective as biocides against algae.
  • the weight ratio of BBIT to lenacil compound is preferably 1 : 10 to 5: 1.
  • the mixture of lenacil and BBIT may be included in a coating composition.
  • Lenacil and BBIT may be added to the coating composition separately or as a mixture or any combination thereof.
  • Preferred coating compositions are liquid.
  • Coating compositions may be aqueous or non-aqueous.
  • Aqueous coating compositions generally contain 30% or more water by weight of the mixture, based on the weight of the coating composition.
  • preferred coating compositions are liquid compositions, especially compositions that contain dispersions of polymers in aqueous media.
  • the antimicrobial compound combinations of the present invention are particularly useful in preservation of building materials, e.g., adhesives, caulk, joint compound, sealant, wallboard, etc., polymers, plastics, synthetic and natural rubber, paper products, fiberglass sheets, insulation, exterior insulating finishing systems, roofing and flooring felts, building plasters, bricks, mortar, gypsum board, wood products and wood-plastic composites.
  • building materials e.g., adhesives, caulk, joint compound, sealant, wallboard, etc., polymers, plastics, synthetic and natural rubber, paper products, fiberglass sheets, insulation, exterior insulating finishing systems, roofing and flooring felts, building plasters, bricks, mortar, gypsum board, wood products and wood-plastic composites.
  • Coating compositions are designed so that a layer of the coating composition can readily be applied to a substrate and then dried or allowed to dry to form a dry film.
  • Coating compositions contain at least one binder. Binders contain one or more of the following: one or more polymer, one or more oligomer, and/or one or more monomer. Oligomers and monomers in binders are designed to polymerize and/or crosslink during or after the formation of the dry film. Polymers in a binder may or may not be designed to crosslink during or after the formation of the dry film.
  • Coating compositions optionally contain one or more pigment.
  • a pigment is a mineral or an organic substance in the form of small solid particles. Pigments provide full or partial opacity to the dry film.
  • the antimicrobial compound combinations are useful for preservation of the dry film coating resulting after application of paint or other liquid coating composition.
  • the antimicrobial composition is an aqueous latex paint comprising one or more of the antimicrobial compound combinations disclosed herein, or the dry film coating resulting from application of the paint to a surface.
  • An aqueous latex paint is an aqueous liquid coating composition in which the binder is a polymer in the form of a latex (i.e., in the form of polymer particles dispersed throughout the water). More preferred are aqueous latex paints in which the binder contains one or more acrylic polymer.
  • the amount of the antimicrobial compound combinations of the present invention to control the growth of microorganisms is from 100 ppm to 40,000 ppm active ingredient.
  • lenacil plus BBIT is present in an amount from 100 ppm to 10,000 ppm.
  • the antimicrobial combinations of the composition are present in an amount of at least 100 ppm and no more than 10,000 ppm, alternatively no more than 8,000 ppm, alternatively no more than 6,000 ppm, alternatively no more than 5,000 ppm, alternatively no more than 3,000 ppm, alternatively no more than 2500 ppm, alternatively no more than 2,000 ppm, alternatively no more than 1 ,000 ppm, and alternatively no more than 500 ppm.
  • Concentrations mentioned above are in a liquid coating composition containing the antimicrobial compound combinations; antimicrobial compound combination levels in the dry film coating will be higher.
  • the present invention also encompasses a method for preventing microbial growth in building materials, especially in dry film coatings, by incorporating any of the claimed antimicrobial compound combinations into the materials.
  • the antimicrobial compositions are used to inhibit growth of algae and/or fungi.
  • composition of the present invention contains lenacil and BBIT. It is contemplated that some embodiments may contain one or more additional antimicrobial compound.
  • acrylic/silicone based outdoor paint free of biocides to give a total active ingredient concentration of 10,000 and l,000ppm respectively.
  • These paints were then diluted with a biocide free acrylic/silicone based paint and mixed to prepare targeted concentrations of biocide combinations for the testing.
  • the total biocides concentrations obtained were 125, 250, 500, 1000, 2000 and 5000 ppm.
  • the paints were mixed 90 seconds with the horse power shaker (AXEL 75M3372/ Agitateur SO-10MI) until uniformity was achieved.
  • the obtained paints containing BBIT and containing lenacil were mixed together to obtain paints containing the two actives in the desired ratios and amounts.
  • the paints were applied to Schleicher & Schuell filter paper at 280 ⁇ wet film thickness and dried for 3 days at room temperature avoiding direct exposure to sunlight.
  • Square discs (1.8 cm x 1.8 cm) were cut out from each panel and were used as the substrate for algal efficacy tests. This sample size allowed for an agar border when the sample disc was placed into the well of the test plate.
  • Algal efficacy was tested according to modified ASTM 5589 which is a standard accelerated test method for determining resistance of various coatings (including paints) to algal defacement. To accommodate for high-throughput screening, this method was scaled down from petri plates to 6-well plates. Bold Modified Basal Freshwater Nutrient Solution was used as growth medium for the algal culture and Bold' s agar was used for the efficacy testing. A single coupon was placed with a pair of sterile forceps at the center of the agar plug (on top) with the painted surface facing upwards. The algal inoculum was prepared by diluting an exponentially growing culture of Chlorella sp. to lx 10 6 cfu/ml.
  • Each well that contains a tested coupon was inoculated with 1750 ⁇ of algal suspension (lx 10 6 cfu/ml) making sure that the whole surface (paint film as well as the agar surrounding it) was evenly covered.
  • the plates were incubated at room temp (21°C - 25 °C) with cyclic exposure to 14 hours fluorescent light followed by 10 hours darkness, for a period of three weeks.
  • SI is calculated based on F.C.Kull et. Al. method (Applied Microbiology, Vol. 9 (1961). In this study, SI was calculated based on the following formula with the minimum inhibitory concentration chosen based on the percent inhibitory exhibited by the individual antimicrobial against each microorganism tested.
  • SI value of ⁇ 1 in the formula indicates a synergism of the blended biocides exists.
  • compositions listed below that contain both lenacil and BBIT are examples of the present invention.
  • Test Results for BBIT with lenacil at three weeks were as follows:

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une composition antimicrobienne synergique contenant du lénacil et du N-butyl-1,2-benzisothiazolin-3-one. L'invention concerne également un procédé d'inhibition de la croissance ou de régulation de la croissance de micro-organismes dans un matériau de construction, une composition de revêtement contenant une telle composition antimicrobienne synergique, et un film sec fabriqué à partir d'une telle composition de revêtement.
PCT/US2017/024953 2016-04-04 2017-03-30 Combinaison synergique constituée d'un composé de lénacil et de n-butyl-1,2-benzisothiazolin-3-one pour une protection sous forme de film sec Ceased WO2017176543A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201780018559.9A CN108882706A (zh) 2016-04-04 2017-03-30 用于干膜保护的环草定化合物与n-丁基-1,2-苯并异噻唑啉-3-酮的协同性组合
BR112018069648A BR112018069648A2 (pt) 2016-04-04 2017-03-30 composição antimicrobiana sinérgica, método para inibir o crescimento ou controlar o crescimento de micro-organismos, composição de revestimento, e, filme seco.
AU2017246163A AU2017246163A1 (en) 2016-04-04 2017-03-30 Synergistic combination of a lenacil compound and N-Butyl-1,2-benzisothiazolin-3-one for dry film protection
MX2018012041A MX2018012041A (es) 2016-04-04 2017-03-30 Combinacion sinergica de compuesto de lenacilo y n-butil-1,2-bencisotiazolin-3-ona para proteccion de pelicula seca.
EP17716416.7A EP3439474A1 (fr) 2016-04-04 2017-03-30 Combinaison synergique constituée d'un composé de lénacil et de n-butyl-1,2-benzisothiazolin-3-one pour une protection sous forme de film sec

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201662317731P 2016-04-04 2016-04-04
US62/317,731 2016-04-04

Publications (1)

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WO2017176543A1 true WO2017176543A1 (fr) 2017-10-12

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Country Status (6)

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EP (1) EP3439474A1 (fr)
CN (1) CN108882706A (fr)
AU (1) AU2017246163A1 (fr)
BR (1) BR112018069648A2 (fr)
MX (1) MX2018012041A (fr)
WO (1) WO2017176543A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190269132A1 (en) * 2016-08-30 2019-09-05 Rohm And Haas Company Synergistic combination of a lenacil compound and 1,2-benzisothiazol-3(2h)-one

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998021962A1 (fr) 1996-11-20 1998-05-28 Troy Corporation Algocide synergique
EP1772055A1 (fr) * 2005-10-04 2007-04-11 Rohm and Haas France SAS Compositions microbicides synergiques comprenant une N-alkyl-1,2-benzoisothiazolin-3-one
WO2014085738A1 (fr) * 2012-11-30 2014-06-05 Rohm And Haas Company Combinaison synergique de lénacile et de l'un parmi dcoit ou oit pour la protection de film sec
WO2014102228A1 (fr) * 2012-12-28 2014-07-03 Sanitized Ag Formulation d'apprêt antimicrobien de compositions polymériques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998021962A1 (fr) 1996-11-20 1998-05-28 Troy Corporation Algocide synergique
EP1772055A1 (fr) * 2005-10-04 2007-04-11 Rohm and Haas France SAS Compositions microbicides synergiques comprenant une N-alkyl-1,2-benzoisothiazolin-3-one
WO2014085738A1 (fr) * 2012-11-30 2014-06-05 Rohm And Haas Company Combinaison synergique de lénacile et de l'un parmi dcoit ou oit pour la protection de film sec
WO2014102228A1 (fr) * 2012-12-28 2014-07-03 Sanitized Ag Formulation d'apprêt antimicrobien de compositions polymériques

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190269132A1 (en) * 2016-08-30 2019-09-05 Rohm And Haas Company Synergistic combination of a lenacil compound and 1,2-benzisothiazol-3(2h)-one

Also Published As

Publication number Publication date
CN108882706A (zh) 2018-11-23
AU2017246163A1 (en) 2018-11-08
EP3439474A1 (fr) 2019-02-13
BR112018069648A2 (pt) 2019-01-29
MX2018012041A (es) 2019-01-14

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