WO1997046095A1 - Halopropargyl inclusion complexes - Google Patents
Halopropargyl inclusion complexes Download PDFInfo
- Publication number
- WO1997046095A1 WO1997046095A1 PCT/US1997/009232 US9709232W WO9746095A1 WO 1997046095 A1 WO1997046095 A1 WO 1997046095A1 US 9709232 W US9709232 W US 9709232W WO 9746095 A1 WO9746095 A1 WO 9746095A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cyclodextrin
- modified
- composition
- inclusion complex
- iodopropargyl
- Prior art date
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- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
Definitions
- This invention is directed to biocidal compositions containing a haloalkynyl
- compositions containing inclusion complexes of such halopropargyl directed to compositions containing inclusion complexes of such halopropargyl
- the present invention is directed to water soluble
- microorganisms are a daunting enemy. They are basically found everywhere on the
- shampoos creams, lotions, cosmetics, soaps, and household products such as laundry detergents, hard surface cleaners, and fabric softeners, as well as numerous other
- biocidal composition containing a large amount of water.
- some of the above applications such as ink, sap stain, leather, textiles, surfactants, thickeners,
- metal working fluids paper pulp, cellulose products, shampoos, creams, lotions, soaps,
- thickeners etc. consist of a large amount of water. For such applications, it is desirable to have a large amount of water.
- biocidal compounds include halogenated compounds
- organometallic compounds quaternary ammonium compounds, phenolics, metallic salts,
- heterocyclic amines heterocyclic amines, formaldehyde donors, organo-sulfur compounds and the like.
- biocidal additives must retain their biocidal activity for a prolonged time period
- biocides are those containing a halopropargyl moiety
- IPBC 2-propargyl butyl carbamate
- IPBC halopropargyl carbamate fungicide
- IPBC also has been associated with algaecidal activity.
- nucleophiles, organic and inorganic acids and bases used in various applications can attack the halo(iodo)propargyl group, with gradual loss of the biocidal activity over time.
- Another kind of halo(iodo)propargyl instability is encountered in the dry film of
- the coating composition in aqueous formulations.
- IPBC 3- iodopropargyl burylcarbamate
- iodopropargyls such as IPBC
- IPBC iodopropargyls
- a limited water solubility i.e. , 50-
- IPBC butylcarbamate
- inclusion complexes of such halopropargyl compounds, and especially IPBC, can be
- FIG 1 schematically illustrates the basic structure of alpha ( ⁇ ), beta ( ⁇ ) and
- gamma ( ⁇ ) cyclodextrins such as before modifications to increase their water solubility.
- Figure 2 graphically presents the stability enhancing effect provided by the
- Cyclodextrins are a group of cyclic, homologous oligosaccharides that are
- transglycosylase such as produced by the bacterium Bacillus macerans. Cyclodextrins were first isolated by F Amsterdam in 1891 as a digest of Bacillus amylobacter on potato starch,
- Cyclodextrins are non-reducing dextrins which have a ring or donut shaped
- ⁇ -cyclodextrin, ⁇ -cyclodextrin and ⁇ -cyclodextrin which consist of 6, 7, and 8 glucopyranose units, respectively, are well known. The structure of these
- atoms are oriented toward, and line the inner cavity of the three-dimensional structure.
- the oligosaccharide ring thus forms a torus, as a truncated cone, with primary hydroxyl
- the cavity is lined by hydrogen atoms from C 3 and C 5 along with the glucosidic
- the parent cyclodextrin molecule, and useful derivatives, can be represented by
- Each cyclodextrin molecule thus can potentially accommodate various kinds of
- cyclodextrins upon complexation, cyclodextrins have the ability to form complexes with a variety of organic and inorganic molecules. The formation of cyclodextrin inclusion complexes with
- ⁇ -, ⁇ -, and ⁇ -cyclodextrins have different physical properties from one another.
- Cyclodextrins generally are
- glucosyltransferase As is well-known, cyclodextrins are produced from starch of any
- selected plant variety such as corn, potato, waxy maize and the like, which may be
- amylopectin fractions thereof are amylopectin fractions thereof.
- the starch in aqueous slurry at a selected concentration up to about 35% by weight solids is usually liquefied as by gelatinization or treatment with a liquefying enzyme such as bacterial alpha-amylase enzyme and then subject to treatment
- cyclodextrins may be increased by a variety of modifications.
- water solubility of ⁇ -cyclodextrin can be increased without necessarily interfering
- the outer hydroxyl groups can be reacted with ethylene oxide, propylene oxide, alkylhalides and the like to render the cyclodextrin, and the inclusion complexes made with the modified molecules water
- aqueous solubility exhibited by such derivatives is due to solvation of the sulfonic acid
- parent cyclodextrins and their modified versions are commercially available.
- the cyclodextrin derivatives are hydroxyalkylated ⁇ -, ⁇ -, ⁇ -cyclodextrins typically having a degree of substitution of 1 to 5.
- the hydroxyalkyl is hydroxyalkylated ⁇ -, ⁇ -, ⁇ -cyclodextrins typically having a degree of substitution of 1 to 5.
- substituents preferably contain 1-4 carbon atoms and up to 2 hydroxy groups. Particularly
- modified cyclodextrins such as hydroxypropyl- ⁇ , hydroxypropyl- ⁇ or hydroxypropyl-
- a halopropargyl compound as the guest.
- inclusion complexes provide protection for the halopropargyl compound guest, surprisingly improving its ability to the adverse effects of nucleophiles,
- aspect of the invention constitutes a water soluble composition containing an inclusion
- a halopropargyl compound for use in the present invention can be identified by
- Y is a halogen, preferably iodine and X can be (1) oxygen which is part of an organic functional group; (2) nitrogen which is part of an organic functional group; (3)
- the functional group of which oxygen is a part is preferably an ether, an ester, a
- a part is preferably an amine, an amide, a urea, a nitrile, a carbamate group, or a
- the functional group of which sulfur is a part is preferably a thiol, a thione, a sulfone, a sulfoxide group, or a heterocyclic compound.
- halopropargyl compound of this invention examples are especially the fungicidally active iodopropargyl derivatives.
- iodopropargyl derivatives include compounds derived from propargyl or iodopropargyl
- alcohols such as the esters, ethers, acetals, carbamates and carbonates and the
- IPBC butyl carbamate
- R is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl groups having from 1 to 20 carbon atoms, aryl, alkylaryl, and aralkyl groups having
- n are independently integers from 1 to 3, i.e. ,
- R substituents include alkyls such as methyl, ethyl, propyl, n-butyl, t-
- cycloalkyls such as cyclopropargyl, cyclohexyl, aryls, alkaryls and aralkyls such as phenyl, benzyl, tolyl,
- aryls such as ethoxyphenyl and the like.
- the inclusion complexes of the present invention are prepared by any method
- cyclodextrin or a modified cyclodextrin derivative is dissolved in water or in an organic solvent
- the mixture then is heated e.g. , to a temperature of about 65°-75°C and the
- the complex may be isolated by any suitable technique for example lyophilization,
- Cyclodextrin inclusion complexes may also be produced by physically grinding or
- the ratio of cyclodextrin or a modified cyclodextrin derivative to halopropargyl compound used to prepare the inclusion complexes of the invention may be any
- the benefits derived from the invention may be obtained by having the molar ratio of cyclodextrin to halopropargyl compound in the range of 10: 1 to 1 : 10 preferably 1 : 1 to
- compositions containing an inclusion complex of the present invention and particularly a water soluble inclusion
- compositions including both concentrated preparations and fully formulated
- compositions generally contain anywhere from about 0.001 to
- compositions protected against microbial attack by the inclusion of a halopropargyl carbamate, can be
- the optimum useful range is about 0.1 %
- compositions are reported as a weight percent
- compositions of the present invention and particularly water
- compositions of the invention contain at least one biocidally active halopropargyl
- water solubility is a matter of degree.
- an inclusion complex is considered water soluble if it has
- the modified cyclodextrin used for this example was a hydroxypropyl alpha
- HPACD hydroxypropyl alpha cyclodextrin
- IPBC IPBC
- IPBC modified cyclodextrin inclusion complex
- the water solubility of the inclusion complex itself was found to be approximately
- composition thus increases the IPBC solubility in water by a factor of 250-300.
- Example 2 prepared in Example 1 was added to 73g water and the mixture was stirred for 1/2 hour.
- ACD Cavitron Alpha cyclodextrin
- IPBC content in the complex was found to be 11.8% by UV absorbance
- inclusion complexes of the invention find particular utility as an ingredient in
- lattices such as acrylic, vinyl acetate acrylic, polyvinyl acetate, styrene butadiene and
- organic materials are present under conditions which allow the growth of undesired
- Example 3 The inclusion complex of Example 3, along with a positive control (Troysan
- Collacral P Water (1 : 1) BASF 3.00 Formulation for Sytrenated Acrylic House Paint
- Example 3 The inclusion complex of Example 3 and Troysan Polyphase R P20T (20% IPBC)
- the melting point of pure IPBC is 66-67°C and its decomposition occurs at about
- the decomposition point of LPBC in the inclusion complex of Examples 1 and 3 was determined to be about 222-
- IPBC inclusion complexes are thermally more stable than
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97928713A EP0926953B1 (en) | 1996-06-04 | 1997-05-30 | Halopropargyl inclusion complexes |
AT97928713T ATE211884T1 (en) | 1996-06-04 | 1997-05-30 | HALOPROPARGYL INCLUSION COMPOUNDS |
CA002257372A CA2257372C (en) | 1996-06-04 | 1997-05-30 | Halopropargyl inclusion complexes |
BRPI9710687-9A BR9710687B1 (en) | 1996-06-04 | 1997-05-30 | halopropargyl inclusion complexes. |
DE69709659T DE69709659T2 (en) | 1996-06-04 | 1997-05-30 | HALOPROPARGYL-INCLUSION COMPOUNDS |
AU32901/97A AU3290197A (en) | 1996-06-04 | 1997-05-30 | Halopropargyl inclusion complexes |
DK97928713T DK0926953T3 (en) | 1996-06-04 | 1997-05-30 | Halogenpropargyline conclusion complexes |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/655,091 | 1996-06-04 | ||
US08/655,091 US5906981A (en) | 1996-06-04 | 1996-06-04 | Halopropargyl inclusion complexes |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997046095A1 true WO1997046095A1 (en) | 1997-12-11 |
Family
ID=24627474
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1997/009232 WO1997046095A1 (en) | 1996-06-04 | 1997-05-30 | Halopropargyl inclusion complexes |
Country Status (13)
Country | Link |
---|---|
US (1) | US5906981A (en) |
EP (1) | EP0926953B1 (en) |
AR (1) | AR007499A1 (en) |
AT (1) | ATE211884T1 (en) |
AU (1) | AU3290197A (en) |
BR (1) | BR9710687B1 (en) |
CA (1) | CA2257372C (en) |
DE (1) | DE69709659T2 (en) |
DK (1) | DK0926953T3 (en) |
ES (1) | ES2171955T3 (en) |
ID (1) | ID17714A (en) |
MY (1) | MY121644A (en) |
WO (1) | WO1997046095A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001039971A (en) * | 1999-07-28 | 2001-02-13 | Nippon Soda Co Ltd | Molecular compound containing tri-o-thymotides as constituent compound |
DE19947182A1 (en) * | 1999-09-30 | 2001-05-03 | Wacker Chemie Gmbh | Wood preservatives, processes for their production and their use |
EP1273638A1 (en) * | 2001-07-05 | 2003-01-08 | Wacker Polymer Systems GmbH & Co. KG | Coating agent for soil resistant coatings |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2002255639B2 (en) | 2001-03-01 | 2008-02-14 | Lonza Inc. | Combination of an iodopropynyl derivative with a ketone acid or its salt and/or with an aromatic carboxylic acid or its salt |
US20050049224A1 (en) * | 2003-08-29 | 2005-03-03 | Gaglani Kamlesh D. | Antimicrobial mixtures comprising iodopropynyl compounds and dimethyldithiocarbamate derivatives |
US7658913B2 (en) * | 2005-11-28 | 2010-02-09 | Verrow Pharmaceuticals, Inc. | Compositions useful for reducing nephrotoxicity and methods of use thereof |
ES2417380B1 (en) | 2012-01-05 | 2014-06-03 | Universidad Del Pais Vasco - Euskal Herriko Unibertsitatea | New pesticide inclusion complexes, compositions containing them and their use as pesticides |
WO2013180777A1 (en) * | 2012-05-30 | 2013-12-05 | Verrow Pharmaceuticals, Inc. | Stabilized formulations containing iodinated contrast agents and cyclodextrins |
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US4259350A (en) * | 1978-03-15 | 1981-03-31 | Sankyo Company Limited | Iodopropargyl derivatives, their use and preparation |
JPH05117105A (en) * | 1991-10-25 | 1993-05-14 | Mitsui Toatsu Chem Inc | Antibacterial/antifungal composition |
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-
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- 1997-05-30 CA CA002257372A patent/CA2257372C/en not_active Expired - Lifetime
- 1997-05-30 DK DK97928713T patent/DK0926953T3/en active
- 1997-05-30 AT AT97928713T patent/ATE211884T1/en active
- 1997-05-30 WO PCT/US1997/009232 patent/WO1997046095A1/en active IP Right Grant
- 1997-05-30 BR BRPI9710687-9A patent/BR9710687B1/en not_active IP Right Cessation
- 1997-05-30 EP EP97928713A patent/EP0926953B1/en not_active Expired - Lifetime
- 1997-05-30 AU AU32901/97A patent/AU3290197A/en not_active Abandoned
- 1997-05-30 ES ES97928713T patent/ES2171955T3/en not_active Expired - Lifetime
- 1997-06-03 AR ARP970102402A patent/AR007499A1/en active IP Right Grant
- 1997-06-04 MY MYPI97002479A patent/MY121644A/en unknown
- 1997-06-04 ID IDP971906A patent/ID17714A/en unknown
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001039971A (en) * | 1999-07-28 | 2001-02-13 | Nippon Soda Co Ltd | Molecular compound containing tri-o-thymotides as constituent compound |
JP4544551B2 (en) * | 1999-07-28 | 2010-09-15 | 日本曹達株式会社 | Molecular compounds containing tri-o-thymotides as component compounds |
DE19947182A1 (en) * | 1999-09-30 | 2001-05-03 | Wacker Chemie Gmbh | Wood preservatives, processes for their production and their use |
EP1273638A1 (en) * | 2001-07-05 | 2003-01-08 | Wacker Polymer Systems GmbH & Co. KG | Coating agent for soil resistant coatings |
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Also Published As
Publication number | Publication date |
---|---|
BR9710687A (en) | 2000-01-11 |
ES2171955T3 (en) | 2002-09-16 |
ID17714A (en) | 1998-01-22 |
EP0926953A1 (en) | 1999-07-07 |
AR007499A1 (en) | 1999-11-10 |
ATE211884T1 (en) | 2002-02-15 |
CA2257372A1 (en) | 1997-12-11 |
DK0926953T3 (en) | 2002-07-01 |
EP0926953B1 (en) | 2002-01-16 |
US5906981A (en) | 1999-05-25 |
CA2257372C (en) | 2007-11-13 |
EP0926953A4 (en) | 1999-10-13 |
MY121644A (en) | 2006-02-28 |
DE69709659T2 (en) | 2002-09-12 |
AU3290197A (en) | 1998-01-05 |
DE69709659D1 (en) | 2002-02-21 |
BR9710687B1 (en) | 2010-02-23 |
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