EP2043433A2 - Holzkonservierungsmittel - Google Patents

Holzkonservierungsmittel

Info

Publication number
EP2043433A2
EP2043433A2 EP07732940A EP07732940A EP2043433A2 EP 2043433 A2 EP2043433 A2 EP 2043433A2 EP 07732940 A EP07732940 A EP 07732940A EP 07732940 A EP07732940 A EP 07732940A EP 2043433 A2 EP2043433 A2 EP 2043433A2
Authority
EP
European Patent Office
Prior art keywords
formulation
compound
carbon atoms
amine oxide
formula
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
EP07732940A
Other languages
English (en)
French (fr)
Inventor
Paul Stuart Warburton
Andrew Stewart Hughes
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.)
Arch Timber Protection Ltd
Original Assignee
Arch Timber Protection Ltd
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 Arch Timber Protection Ltd filed Critical Arch Timber Protection Ltd
Publication of EP2043433A2 publication Critical patent/EP2043433A2/de
Ceased legal-status Critical Current

Links

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
    • A01N43/64—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
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds only one oxygen atom attached to the nitrogen atom
    • 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
    • A01N43/72—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
    • A01N43/74—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 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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

Definitions

  • the amine oxide is represented by the general formula (II) R 2
  • C 1-5 alkyl group e.g. t-butyl
  • R represents a phenyl group optionally substituted by one or more substituents selected from halogen (e.g. chlorine, fluorine or bromine) atoms or C 1-3 alkyl (e.g. methyl), C 1-3 alkoxy (e.g. methoxy) , phenyl or nitro groups.
  • halogen e.g. chlorine, fluorine or bromine
  • C 1-3 alkyl e.g. methyl
  • C 1-3 alkoxy e.g. methoxy
  • the compound of formula (I) is positively charged, it is accompanied by an anion X " which is chosen to allow ready water solubility.
  • suitable anions include chloride, bromide, sulphate, acetate, propionate, lactate, citrate, methosulphate, hydroxide, carbonate and bicarbonate.
  • R 1 and R 2 are alkyl groups which may be the same or different and which contain from 6 to 22 carbon atoms, preferably from 8 to 10 carbon atoms in a dialkyl compound and from 10 to 14 carbon atoms in a monoalkyl compound, most preferably 10 carbon atoms, .m is a number from 1 to 20 typically from 1 to 8, preferably from 3.to 5.
  • X " is an anion of the type previously described, preferably propionate or lactate.
  • the compound of formula (I) may be a dimethylalkylamine or salt thereof.
  • a dimethylalkylamine is an N,N-dimethyl-N-alkylamine where alkyl represents an alkyl chain with 6 to 20 carbon atoms , preferably 12 to 14 carbon atoms .
  • alkyl represents an alkyl chain with 6 to 20 carbon atoms , preferably 12 to 14 carbon atoms .
  • mixtures for example dimethyl-C 12 -alkylamine and dimethyl-C 14 alkylamine (dimethyl-C 12 /C 14 -alkylamine) .
  • Suitable additional fungicides include for example, dichlofluanid, acypetacs, including copper and zinc salts, isothiazolones, tolyfluanid, chlorothanonil , fenpropimorph, sorbic acid and salts thereof, borates, guazatine and salts thereof, benzoic acid and its salts, oxathiazines , TCMTB, MBT, PCP and its salts, N- (3-aminopropyl) -N-dodecylpropane-1, 3- diamine, Dazomet, (E) -1- (2-chloro-l, 3-thiazol-5- ylmethyl-2-nitroguanadine, as well as metal compounds such as copper, Cu-oxide, copper naphthenate, copper carbonate, copper oxine, copper hydroxide, copper dihydroxide, Cu-HDO, potassium-HDO, also iron and- zinc and salts, compounds and soaps thereof.
  • Figure 8 is a graph showing the performance of AT27M (AT26 plus mixed C12/C16 amine oxides) applied during the test of Example 2.
  • Figure 9 is a graph showing the performance of AT15M
  • Figure 12 is a graph showing the performance of AT6 applied at 0.69% applied during the test of Example 3.
  • Figure 20 is a graph showing the performance of ATF2 (ATFl without the IPBC) applied during the test of Example 4.
  • the wood used for the trial was freshly sawn Southern Yellow Pine obtained locally in Florida. For each formulation a total of 25 boards each measuring 25mm x 100mm x 600mm were tested.
  • Benzalkonium chloride (80% a.i.) 62.5% w/w
  • IPBC (98% a.i. ) 5.1 Propiconazole (50% a.i.) 10.0
  • Figure 6 shows the effect of including thiabendazole and mixed C12/C16 amine oxides.
  • AT7M is AT6A plus both 1% Thiabendazole and 8% mixed amine oxides.
  • Figure 8 shows the effect of including Imazalil and mixed C12/C16 amine oxides.
  • AT27M is AT6A plus both 2% imazalil and 8% mixed C12/C16 amine oxides.
  • This example shows the results of a field trial conducted in Portugal.
  • C16 amine oxide was used and incorporated in to the base formulation AT6 as used in Example 1 at 10% such that the add-on cost to the formulation was also around 10%.
  • the formulation was labeled as AT9.
  • the dipping was performed in open tanks containing 40 liters of solution. The samples were immersed in the bath for 1 min. Next, wood was stored fro 10 min in a special stand in order to allow draining of excess product. 30 samples were dipped for each product and concentration. The wood was stored in 48cm wide stacks (5 samples were stored parallel in a single layer) . The samples were stored without stickers (closed stacked) .
  • the levels of active ingredients (BAC, propiconazole and IPBC) in the wood are very close for each product at the two solution strengths tested. That is to say that 1.03% AT6 treated timber has rather similar levels of actives to 0.93% AT9 and so on. In fact the levels in the AT9 treated wood are slightly lower that in the AT6 due to the added cost of the Cl ⁇ amine oxide and the desire to compare performance of the two formulations at equivalent cost in the wood.
  • Figure 17 shows the performance of the control benzalkonium chloride, propiconazole and IPBC formulation (AT6A) and as such establishes the criteria by which the alternatives are judged. Details of this formulation are given in Example 2. 7 boards out of 35 have reached Grade 2 or above, hence the failure rate is 20%.
  • Figure 23 shows the performance of a composition wherein the quaternary ammonium compound, triazole and imidazole of AT7A have been replaced with dimethyldidecylammonium carbonate/bicarbonate, hexaconazole and imazalil respectively.
  • This is example ATF5.
  • the lack of failures to sapstain clearly shows the suitability of this azole, imidazole and quaternary ammonium compound for the synergistic mixture.
  • Formulation 8 C12 amine oxide (30% a. i.) 6.0% w/w
  • IPBC (98% a.i. ) 2.45
  • IPBC (98% a.i. ) 2.45
  • Benzalkonium chloride (80% a.i.) - 62.5% w/w '
  • IPBC (98% a.i. ) 5.1 Propiconazole (50% a.i.) 10.0
  • Benzalkonium chloride (80% a. i.) 62.5% w/w
  • Benzalkonium chloride (80% a.i.) 62.5% w/w

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Forests & Forestry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP07732940A 2006-05-24 2007-05-24 Holzkonservierungsmittel Ceased EP2043433A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0610336A GB2438404A (en) 2006-05-24 2006-05-24 Preserving wood with an amine oxide, an azole and a specified amine or quaternary ammonium compound, in synergistic proportions
PCT/GB2007/001919 WO2007135435A2 (en) 2006-05-24 2007-05-24 Wood preservative formulations

Publications (1)

Publication Number Publication Date
EP2043433A2 true EP2043433A2 (de) 2009-04-08

Family

ID=36687677

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07732940A Ceased EP2043433A2 (de) 2006-05-24 2007-05-24 Holzkonservierungsmittel

Country Status (5)

Country Link
EP (1) EP2043433A2 (de)
AU (1) AU2007253048B2 (de)
GB (1) GB2438404A (de)
NZ (2) NZ596157A (de)
WO (1) WO2007135435A2 (de)

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* Cited by examiner, † Cited by third party
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GB2459691B (en) * 2008-04-30 2013-05-22 Arch Timber Protection Ltd Formulations
AU2014200779B8 (en) * 2008-04-30 2015-11-19 Arch Timber Protection Limited Antisapstain compositions comprising a haloalkynyl compound, an azole and an unsaturated acid
GB2479556A (en) 2010-04-13 2011-10-19 Arch Timber Protection Ltd Wood preservative formulation
WO2012002826A1 (en) * 2010-06-29 2012-01-05 Zelam Limited Synergistic fungicidal compositions and methods of use
US9125398B2 (en) * 2011-04-05 2015-09-08 Kop-Coat, Inc. Method of employing enhanced penetration of wood preservatives to protect wood and a related solution
CA2970204A1 (en) * 2014-12-15 2016-06-23 Akzo Nobel Chemicals International B.V. Weatherproof aqueous wood coatings
US20160286798A1 (en) * 2015-03-31 2016-10-06 Kop-Coat, Inc. Solutions for enhancing the effectiveness of insecticides and fungicides on living plants and related methods
US11779016B2 (en) 2015-03-31 2023-10-10 Kop-Coat, Inc. Solutions for enhancing the effectiveness of insecticides and fungicides on living plants and related methods
US10952433B2 (en) 2015-03-31 2021-03-23 Kop-Coat, Inc. Solutions for enhancing the effectiveness of insecticides and fungicides on living plants and related methods
US9717246B1 (en) * 2016-05-24 2017-08-01 Kop-Coat, Inc. Method and related solution for protecting wood through enhanced penetration of wood preservatives employing buffered amine oxides and alkoxylated oils
JP2022543694A (ja) * 2019-08-09 2022-10-13 トロイ コーポレイション 高分子ベタインとカーバメートを含む相乗効果のある木材保存組成物
WO2023239303A1 (en) * 2022-06-07 2023-12-14 Hydroemission Corporation Pte. Ltd. Plant treatment compositions and preparation thereof

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See also references of WO2007135435A2 *

Also Published As

Publication number Publication date
WO2007135435A3 (en) 2008-05-29
AU2007253048A1 (en) 2007-11-29
NZ596157A (en) 2013-05-31
NZ573995A (en) 2011-11-25
GB2438404A (en) 2007-11-28
GB0610336D0 (en) 2006-07-05
AU2007253048B2 (en) 2013-03-21
WO2007135435A2 (en) 2007-11-29

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