EP4009791A1 - Synergistische holzschutzmittelzusammensetzung mit polymerem betain und carbamat - Google Patents

Synergistische holzschutzmittelzusammensetzung mit polymerem betain und carbamat

Info

Publication number: EP4009791A1
Authority: EP; European Patent Office
Prior art keywords: composition; wood; ipbc; weight; polymeric
Prior art date: 2019-08-09
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.): Pending

Application number

EP20760709.4A

Other languages

English (en)

French (fr)

Inventor

Min Chen

Jake Zachary JACOBS

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.)

Troy Corp

Original Assignee

Troy Corp

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.)

2019-08-09

Filing date

2020-08-07

Publication date

2022-06-15

2020-08-07 Application filed by Troy Corp filed Critical Troy Corp

2022-06-15 Publication of EP4009791A1 publication Critical patent/EP4009791A1/de

Status Pending legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 53
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 title claims abstract description 30
229960003237 betaine Drugs 0.000 title claims abstract description 28
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 title claims abstract description 26
230000002195 synergetic effect Effects 0.000 title claims abstract description 11
239000003171 wood protecting agent Substances 0.000 title description 9
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 title description 5
229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 claims abstract description 31
WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 claims abstract description 31
239000002023 wood Substances 0.000 claims abstract description 31
244000005700 microbiome Species 0.000 claims abstract description 20
238000000034 method Methods 0.000 claims abstract description 9
238000004321 preservation Methods 0.000 claims abstract description 5
239000002904 solvent Substances 0.000 claims description 17
239000000243 solution Substances 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
239000000839 emulsion Substances 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
LKZVYRAXTFZCMF-UHFFFAOYSA-N B([O-])([O-])[O-].C(CCCCCCCCC)[N+](CCO)(CCO)CCCCCCCCCC.C(CCCCCCCCC)[N+](CCCCCCCCCC)(CCO)CCO.C(CCCCCCCCC)[N+](CCCCCCCCCC)(CCO)CCO Chemical compound B([O-])([O-])[O-].C(CCCCCCCCC)[N+](CCO)(CCO)CCCCCCCCCC.C(CCCCCCCCC)[N+](CCCCCCCCCC)(CCO)CCO.C(CCCCCCCCC)[N+](CCCCCCCCCC)(CCO)CCO LKZVYRAXTFZCMF-UHFFFAOYSA-N 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
238000007654 immersion Methods 0.000 claims description 2
239000007921 spray Substances 0.000 claims description 2
239000003125 aqueous solvent Substances 0.000 claims 1
239000003849 aromatic solvent Substances 0.000 claims 1
239000002798 polar solvent Substances 0.000 claims 1
-1 iodopropynyl compound Chemical class 0.000 description 17
150000001875 compounds Chemical class 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
125000000524 functional group Chemical group 0.000 description 8
230000002538 fungal effect Effects 0.000 description 7
239000000758 substrate Substances 0.000 description 7
239000012141 concentrate Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000012360 testing method Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
230000000845 anti-microbial effect Effects 0.000 description 4
239000000463 material Substances 0.000 description 4
239000003755 preservative agent Substances 0.000 description 4
230000002335 preservative effect Effects 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000004480 active ingredient Substances 0.000 description 3
230000002411 adverse Effects 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000006378 damage Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
241000223678 Aureobasidium pullulans Species 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
IABBAGAOMDWOCW-UHFFFAOYSA-N Nicametate citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CCN(CC)CCOC(=O)C1=CC=CN=C1 IABBAGAOMDWOCW-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
241001136494 Talaromyces funiculosus Species 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
230000006866 deterioration Effects 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
230000036512 infertility Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
238000011282 treatment Methods 0.000 description 2
230000000007 visual effect Effects 0.000 description 2
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
HPGGRRWTQXPMHJ-UHFFFAOYSA-N 3-iodoprop-1-ynyl carbamate Chemical class NC(=O)OC#CCI HPGGRRWTQXPMHJ-UHFFFAOYSA-N 0.000 description 1
241000228212 Aspergillus Species 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000195493 Cryptophyta Species 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
241000223259 Trichoderma Species 0.000 description 1
241001304120 Trichoderma pseudokoningii Species 0.000 description 1
241001557886 Trichoderma sp. Species 0.000 description 1
239000012963 UV stabilizer Substances 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000004171 alkoxy aryl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
238000002827 antifungal susceptibility testing Methods 0.000 description 1
239000002635 aromatic organic solvent Substances 0.000 description 1
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000003139 biocide Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
229920005556 chlorobutyl Polymers 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [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])* 0.000 description 1
230000002542 deteriorative effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
125000003438 dodecyl group Chemical group [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])* 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000834 fixative Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
230000036541 health Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000004530 micro-emulsion Substances 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
239000013642 negative control Substances 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
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
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
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
238000012545 processing Methods 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
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000979 retarding effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
241000894007 species Species 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
125000001424 substituent group Chemical group 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
231100000583 toxicological profile Toxicity 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000012224 working solution Substances 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
- 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
- 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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/50—Mixtures of different organic impregnating agents
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K2240/00—Purpose of the treatment
- B27K2240/20—Removing fungi, molds or insects

Definitions

the present invention pertains to synergistic compositions suitable for use in the treatment and preservation of wood and wood products.
the antimicrobial compositions of this invention include wood preservative compositions comprising a polymeric betaine and an iodopropynyl compound. These combinations are especially useful in protecting wood and wood products from spoilage resulting from the growth of microorganisms, especially microorganisms that produce mold and sapstain.
antimicrobial materials included halogenated compounds, organometallic compounds, quaternary ammonium compounds, phenolics, metallic salts, heterocyclic amines, formaldehyde adducts, organosulfur compounds, and the like.
No single organic antimicrobial compound is able to provide protection against all microorganisms and is suitable for all applications.
other limitations may restrict the usefulness of certain antimicrobials. For example the stability, physical properties, toxicological profile, regulatory considerations, economic considerations or environmental concerns may render a particular ingredient unsuitable for a particular use. There is a need, therefore, to constantly develop new combinations that will offer broad spectrum protection from a variety of needs.
a judicious choice of combinations may provide a way to maximize benefits while at the same time minimize problems.
a combination wherein the antimicrobial activity is enhanced while the less desirable properties are suppressed or reduced can provide a superior product.
the task is to find such combinations that will provide protection against a wide variety of problem microorganisms, will not adversely affect the product to be protected, will maintain its integrity for an extended period of time, and will not have any strong adverse effects on health or the environment.
the present invention is directed to certain synergistic preservative compositions comprising a polymeric betaine and an iodopropynyl compound.
the present invention is also directed to methods for controlling mold and/or sapstain on wood or wood products by application of an effective amount of such compositions to the wood or wood product substrate.
iodopropynyl compounds such as 3-iodo-2- propynyl butyl carbamate (IPBC) are combined with polymeric betaines such as didecyl bis(hydroxyethyl) ammonium borate (DPAB), they form wood preservative compositions that are surprisingly more effective against microorganisms that produce mold and/or sapstain on wood or wood products than either single component alone.
polymeric betaines and iodopropynyl compounds complement one another in a way that could not be anticipated.
the polymeric betaines and iodopropynl compound show synergistic activity. This unexpected synergistic activity offers a number of advantages in the preservation of wood and wood products.
This invention relates to the synergistic wood preservative composition
polymeric betaine or more precisely didecyl bis(hydroxyethyl) ammonium borate (DPAB), and 3-iodo-2-propynyl butyl carbamate having the properties of providing effective and broader control of microorganisms that produce mold and sapstain.
DPAB didecyl bis(hydroxyethyl) ammonium borate
3-iodo-2-propynyl butyl carbamate having the properties of providing effective and broader control of microorganisms that produce mold and sapstain.
Suitable polymeric betaines are described in, for example, U.S. Patent No. 5,304,237, the entire contents of which are incorporated herein by reference.
the structural formula of DPAB is:
the antisapstain compositions of the invention can be prepared as solutions or emulsions by conventional means by using water or organic liquids as a solvent.
a preferred form
the quantity and ratio of polymeric betaine and IPBC will depend upon the specific application.
the wood preservative composition will contain from about 1 to 100 parts by weight polymeric betaine per about 1 to 100 parts by weight IPBC. More preferably, the composition will contain about 1 to 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, or 1 to 40 parts by weight of polymeric betaine per 1 to 90, 1 to 80, 1 to 70, 1 to 60, 1 to 50, or 1 to 40 parts by weight of IPBC.
a preferred weight ratio of polymeric betaine to IPBC is from about 30:1 to about 1:30, more preferably 20: 1 to 1:20, even more preferably 10:1 to 1: 10.
a particularly preferred ratio of polymeric betaine to IPBC is from 5: 1 to 10: 1 parts by weight, i.e., about 5 to 10 parts by weight polymeric betaine per part by weight IPBC.
Other preferred ratios of polymeric betaine to IPBC include 1: 1, 2: 1 to 1:2, 3:2 to 2:3, 3:1 to 1:3, 4: 1 to 1:4, 4:3 to 3:4, 5: 1 to 1:5, 5:2 to 2:5, 5:3 to 3:5, 5:4 to 4:5, 6: 1 to 1:6, 6:5 to 5:6, 7: 1 to 1:7, 7:2 to 2:7, 7:3 to 3:7, 7:4 to 4:7, 7:5 to 5:7, 7:6 to 6:7, 8:1 to 1:8, 8:3 to 3:8, 8:5 to 5:8, 8:7 to 7:8, 9: 1 to 1:9, 9:2 to 2:9, 9:4 to 4:9, 9:5 to 5:9, 9:7 to 7
the preservative composition may be advantageous to supply the preservative composition in concentrated form with about 15, 20, 25, 30, 35, 40, or 45 percent by weight of solvent to about 50, 55, 60, 65, 70, 75, or 80 percent by weight solvent.
the composition may comprise more than 80 percent by weight of solvents, for example from 80 to 99.9, 85 to 99.9, 90 to 99.9, 90.5 to 99.9, 91 to 99.9, 91.5 to 99.9, 92 to 99.9, 92.5 to 99, 93 to 99.9, or 95 to 99.9 percent by weight of solvent.
Typical solvents include water and/or organic solvents, including aromatic organic solvents, polar and non-polar organic solvents, and aliphatic organic solvents.
the concentrate is generally diluted about 10 to 200 times to working solution strength by the addition of water (or another solvent).
the diluted solution or emulsion can be applied to wood by conventional treating methods such as immersion, brush, spray, flooding, or pressure.
antimicrobial mixtures provide a high level of activity over a prolonged period, providing the strengths of the individual ingredients while minimizing the weaknesses of each. It is this type of complimentary activity that allows one to use less biocide in combination to achieve a desired effect at levels that cannot be achieved with any of the individual ingredients.
halopropynyl compounds that can be used in accordance with the present invention, for the most part, are well known and can be generally identified by the following structure:
YC C-CH 2 X
X can be (1) oxygen that is part of an organic functional group; (2) nitrogen that is part of an organic functional group; (3) sulfur that is part of an organic functional group; or (4) carbon that is part of an organic functional group.
the functional group of which oxygen is a part is preferably an ether, an ester, or a carbamate group.
the functional group of which nitrogen is a part is preferably an amine, an amide, or a carbamate group.
the functional group of which sulfur is a part is preferably a thiol, a thiane, a sulfone, or a sulfoxide group.
the organic functional group of which carbon is a part is preferably an ester, a carbamate or an alkyl group.
Examples of compounds that may be used as the halopropynyl compound of this invention are especially the active iodopropynyl derivatives some of which are reported in U.S. Pat. Nos. 3,923,870; 4,259,350; 4,592,773; 4,616,004; 4,719,227; and 4,945,109.
iodopropynyl derivatives include compounds derived from propynyl or iodopropynyl alcohols such as esters, acetals, carbamates and carbonates and further include the iodopropynyl derivatives of pyrimidines, thiazolinones, tetrazoles, triazinones, sulfamides, benzothiazoles, ammonium salts, carboxamides, and ureas.
R may have one to three linkages corresponding to n and is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl groups having from 1 to 20 carbon atoms, substituted and unsubstituted aryl, alkylaryl, and aralkyl of from 6 to 20 carbon atoms or cycloalkyl and cycloalkenyl groups of from 3 to 10 carbon atoms, and m and n are independently integers from 1 to 3, i.e., they are not necessarily the same.
Suitable R substituents include alkyls such as methyl, ethyl, propyl, n-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, and octadecyl; cycloalkyls such as cyclohexyl; aryls, alkaryls and aralkyls such as phenyl, benzyl, tolyl, and cumyl; halogenated alkyls and aryls, such as chlorobutyl and chlorophenyl; and alkoxy aryls such as ethoxyphenyl and the like.
iodopropynyl carbamates as 3-iodo-2-propynyl propyl carbamate, 3-iodo-2-propynyl butyl carbamate, 3-iodo-2-propynyl hexyl carbamate, 3-iodo-2-propynyl cyclohexyl carbamate, 3-iodo-2-propynyl phenyl carbamate, and mixtures thereof.
compositions of the present invention will generally be formulated by mixing or dispersing the active ingredients in a selected proportion with a liquid vehicle for dissolving or suspending the active components.
the vehicle may contain a diluent, an emulsifier, and a wetting-agent.
Expected uses of the biocidal compositions include the protection of wood, wood products, fresh sawn timber, and the like.
the compositions of this invention may be provided as liquid mixtures such as dispersions, emulsions, microemulsions, or in any other suitable product form that is desirable or most useful.
the composition also will likely be provided with adjuvants conventionally employed in compositions intended for such applications such as organic binding agents, additional fungicides, auxiliary solvents, processing additives, fixatives, plasticizers, UV-stabilizers or stability enhancers, water soluble or water insoluble dyes, color pigments, siccatives, corrosion inhibitors, antisettlement agents, anti-skinning agents and the like.
adjuvants conventionally employed in compositions intended for such applications such as organic binding agents, additional fungicides, auxiliary solvents, processing additives, fixatives, plasticizers, UV-stabilizers or stability enhancers, water soluble or water insoluble dyes, color pigments, siccatives, corrosion inhibitors, antisettlement agents, anti-skinning agents and the like.
substrates are protected from contamination by microorganisms simply by treating said substrate with a composition of the present invention. Such treating may involve mixing the composition with the substrate, coating or otherwise contacting the substrate with the composition and the like.
IPBC solvent solution Polyphase AF-1, Troy Chemical Corporation, Newark, NJ
Suspension strength was determined via hemocytometer then adjusted to lxlO 6 spores/mL with sterile deionized water.
MIC Minimum inhibitory concentration
Table 4 The growth of Trichoderma oseudokoninaii (ATCC# 268011 in 96-well plates containing selected concentrations of DPAB. IPBC and their mixture. The values stated wells 1 through 12 are in ppm active.
MCA Concentration of compound A in parts per million, acting alone, which prevents fungal growth at the reference point
MCA' Concentration of compound A in parts per million, in the mixture, which prevents fungal growth at the reference point
MCB Concentration of compound B in parts per million, acting alone, which prevents fungal growth at the reference point

Landscapes

Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Forests & Forestry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Chemical And Physical Treatments For Wood And The Like (AREA)

EP20760709.4A 2019-08-09 2020-08-07 Synergistische holzschutzmittelzusammensetzung mit polymerem betain und carbamat Pending EP4009791A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US201962884738P	2019-08-09	2019-08-09
PCT/US2020/045452 WO2021030202A1 (en)	2019-08-09	2020-08-07	Synergistic wood preservative composition comprising polymeric betaine and carbamate

Publications (1)

Publication Number	Publication Date
EP4009791A1 true EP4009791A1 (de)	2022-06-15

Family

ID=72179257

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP20760709.4A Pending EP4009791A1 (de)	2019-08-09	2020-08-07	Synergistische holzschutzmittelzusammensetzung mit polymerem betain und carbamat

Country Status (8)

Country	Link
EP (1)	EP4009791A1 (de)
JP (1)	JP2022543694A (de)
KR (1)	KR20220044326A (de)
CN (1)	CN114206112B (de)
AU (1)	AU2020327938A1 (de)
BR (1)	BR112022001840A2 (de)
CA (1)	CA3149341C (de)
WO (1)	WO2021030202A1 (de)

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3923870A (en)	1973-07-11	1975-12-02	Troy Chemical Corp	Urethanes of 1-halogen substituted alkynes
US4259350A (en)	1978-03-15	1981-03-31	Sankyo Company Limited	Iodopropargyl derivatives, their use and preparation
IL75979A (en)	1984-08-10	1988-10-31	Mitsui Toatsu Chemicals	Propargyloxyacetonitrile derivatives,their preparation and fungicidal and herbicidal compositions containing them
US4616004A (en)	1984-09-27	1986-10-07	Chevron Research Company	1-iodopropargyl-3,4-disubstituted-Δ2 -1,2,4-triazolidin-5-one fungicides
DE3510203A1 (de)	1985-03-21	1986-09-25	Bayer Ag, 5090 Leverkusen	Neue iodpropargylether, ein verfahren zu ihrer herstellung und ihre verwendung
DE3827721A1 (de) *	1988-08-16	1990-02-22	Ruetgerswerke Ag	Mittel zum konservieren von holz und ihre verwendung
US4945109A (en)	1988-08-24	1990-07-31	Buckman Laboratories International, Inc.	Ester of carbamic acid useful as a microbicide and a preservative
US4950685A (en) *	1988-12-20	1990-08-21	Kop-Coat, Inc.	Wood preservatives
DE4228352A1 (de)	1992-02-19	1993-08-26	Ruetgerswerke Ag	Chromfreies holzschutzmittel
NZ320144A (en) *	1995-09-29	1999-08-30	Rohm & Haas	Dry wood preservative comprising one or more insect hormones, preferably phenoxycarb, at a concentration of 0.00005%-0.5% by weight
NZ507060A (en) *	2000-09-20	2003-08-29	Osmose New Zealand	Wood preservation compositions and procedures
JP2004524321A (ja) *	2001-03-01	2004-08-12	ロンザインコーポレイテッド	ヨードプロピニル誘導体とケトン酸若しくはその塩及び／又は芳香族カルボン酸若しくはその塩との併用法
CA2539185A1 (en) *	2003-09-19	2005-03-31	Arch Chemicals, Inc.	Stabilized halopropynyl compositions as preservatives
DE102004036918A1 (de) *	2004-07-29	2007-02-08	Georg-August-Universität Göttingen	Schutzmittel und Vergütung für Holz
GB2438404A (en) *	2006-05-24	2007-11-28	Arch Timber Protection Ltd	Preserving wood with an amine oxide, an azole and a specified amine or quaternary ammonium compound, in synergistic proportions
US20100003345A1 (en) *	2008-07-02	2010-01-07	Kamlesh Gaglani	Synergistic antimicrobial mixtures
EP3085505A1 (de) *	2015-04-24	2016-10-26	RÜTGERS Organics GmbH	Zusammensetzung mit einer wirkstoffzusammensetzung und einer additivzusammensetzung zur penetration von holz
US10119034B2 (en) *	2015-10-09	2018-11-06	Ziqiang Lu	Wood preservation products protected with a durable coating system
CN106217580A (zh) *	2016-08-23	2016-12-14	宁波大诚和电子有限公司	一种改进型便携音箱
JP2024511719A (ja) *	2021-03-19	2024-03-15	アークサーダ・リミテッド・ライアビリティ・カンパニー	亜鉛およびホウ素含有強化木材防腐剤

2020
- 2020-08-07 KR KR1020227007644A patent/KR20220044326A/ko unknown
- 2020-08-07 JP JP2022507888A patent/JP2022543694A/ja active Pending
- 2020-08-07 EP EP20760709.4A patent/EP4009791A1/de active Pending
- 2020-08-07 AU AU2020327938A patent/AU2020327938A1/en not_active Abandoned
- 2020-08-07 CN CN202080056180.9A patent/CN114206112B/zh active Active
- 2020-08-07 CA CA3149341A patent/CA3149341C/en active Active
- 2020-08-07 WO PCT/US2020/045452 patent/WO2021030202A1/en unknown
- 2020-08-07 BR BR112022001840A patent/BR112022001840A2/pt unknown

Also Published As

Publication number	Publication date
CN114206112B (zh)	2024-04-12
KR20220044326A (ko)	2022-04-07
AU2020327938A1 (en)	2022-02-24
BR112022001840A2 (pt)	2022-06-21
WO2021030202A1 (en)	2021-02-18
CA3149341C (en)	2024-03-05
CA3149341A1 (en)	2021-02-18
JP2022543694A (ja)	2022-10-13
CN114206112A (zh)	2022-03-18

Legal Events

Date	Code	Title	Description
2020-08-31	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: UNKNOWN
2021-02-19	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE
2022-05-13	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
2022-05-13	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE
2022-06-15	17P	Request for examination filed	Effective date: 20220209
2022-06-15	AK	Designated contracting states	Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
2022-11-16	DAV	Request for validation of the european patent (deleted)
2022-11-16	DAX	Request for extension of the european patent (deleted)
2024-03-22	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: EXAMINATION IS IN PROGRESS
2024-04-24	17Q	First examination report despatched	Effective date: 20240321

Publication	Publication Date	Title
US4655815A (en)	1987-04-07	Admixtures of 2-bromo-2-bromomethylglutaronitrile and a formaldehyde donor
KR0179468B1 (ko)	1999-04-01	4,5-디클로로-2-옥틸-3-이소티아졸론과 특정 상업용 살생물제를포함하는 상승작용의 살균제 배합물
JP3488015B2 (ja)	2004-01-19	ハロプロピニル化合物と硫黄含有トリアジンとの混合物を含む殺生物剤組成物
AU762644B2 (en)	2003-07-03	Broad spectrum antimicrobial mixtures
WO1998021962A1 (en)	1998-05-28	Synergistic algaecide
US5733362A (en)	1998-03-31	Synergistic bactericide
CA2041349A1 (en)	1991-10-28	Biocide composition and use
EP0196452B1 (de)	1990-06-20	Synergistische, antimikrobische Beimischungen, enthaltend 2-Bromo-2-bromomethylglutaronitril, Verfahren zur Hemmung mikrobischen Wachstums und gegen mikrobisches Wachstum geschützte Substrate
US6140370A (en)	2000-10-31	Stabilized alkyd based compositions containing halopropynl compounds
JPH04295404A (ja)	1992-10-20	抗菌組成物及びその使用
JPH10175809A (ja)	1998-06-30	工業用殺菌組成物
US20170142972A1 (en)	2017-05-25	Antimicrobial composition inhibits bacteria and fungi
CA3149341C (en)	2024-03-05	Synergistic wood preservative composition comprising polymeric betaine and carbamate
US6576230B1 (en)	2003-06-10	Biocidal mixture of 2-propenal-releasing polymer and isothiazolones
US20220161456A1 (en)	2022-05-26	Synergistic wood preservative composition comprising polymeric betaine and carbamate
NZ330286A (en)	2000-09-29	Wood staining/destroying fungus biocide comprising iodocarb