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Patent 2185556 Summary

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(12) Patent Application: (11) CA 2185556
(54) English Title: COMBINATIONS OF ACTIVE INSECTICIDE SUBSTANCES
(54) French Title: COMBINAISONS DE PRINCIPES ACTIFS INSECTICIDES
Status: Dead
Bibliographic Data
(51) International Patent Classification (IPC):
  • B27K 3/50 (2006.01)
  • A01N 47/34 (2006.01)
(72) Inventors :
  • UHR, HERMANN (Germany)
  • KUGLER, MARTIN (Germany)
  • KUNISCH, FRANZ (Germany)
  • BUSCHHAUS, HANS-ULRICH (Germany)
(73) Owners :
  • BAYER AKTIENGESELLSCHAFT (Germany)
(71) Applicants :
(74) Agent: FETHERSTONHAUGH & CO.
(74) Associate agent:
(45) Issued:
(86) PCT Filing Date: 1995-03-06
(87) Open to Public Inspection: 1995-09-21
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/EP1995/000827
(87) International Publication Number: WO1995/024997
(85) National Entry: 1996-09-13

(30) Application Priority Data:
Application No. Country/Territory Date
P 44 09 040.4 Germany 1994-03-17

Abstracts

English Abstract


The present application relates to new active combinations which are com-
posed, on the one hand, of triflumuron, which is known, and, on the other
hand, of other known active compounds, and which are highly suitable for the
protection of industrial materials.


French Abstract

De nouvelles combinaisons de principes actifs constituées d'un principe actif connu, le triflumuron, et d'autres principes actifs connus conviennent très bien pour protéger des matériaux techniques.

Claims

Note: Claims are shown in the official language in which they were submitted.


- 18 -
Patent Claims

1. Wood preservative comprising triflumuron and at least one synergistically
complementing active compound.
2. Wood preservative according to Claim 1, additionally comprising at least
one azole fungicide.
3. Composition or concentrate for the preservation of wood and derived
timber products based on, or also comprising, triflumuron and at least
one solvent, diluent and/or additive, characterized in that the composi-
tion or concentrate comprises 0.01 to 25 % by weight of triflumuron as
a mixture with 0.1 to 99.9 % by weight of at least one fungicide and over
40 % by weight of a mixture of solvent and/or diluent and/or organo-
chemical binder and/or fixative, processing auxiliary, colorant, pigment,
colorant mixture or pigment mixture.
4. Composition or concentrate according to Claim 3, characterized in that
the solvent and/or diluent comprises an organochemical solvent or
solvent mixture and/or an oily or oil-type organochemical solvent or
solvent mixture of low volatility and/or a polar organochemical solvent
or solvent mixture and/or water in combination with at least one emul-
sifier and/or wetting agent.
5. Wood preservative according to one or more of Claims 1 to 4, character-
ized in that it comprises, as the azole,
Azaconazole:
1-{[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl}1-H-1,2,4-tria-
zoles
Propiconazole:
1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl-1-H-


- 19 -
1,2,4-triazoles
Tebuconazole:
1-p-chlorophenyl-4,4-dimethyl-3(1H-1,2,4-triazol-1-y 1-methyl)pentan-
3-ol
Cyproconazole:
2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-1H-(1,2,4-triazol-
1yl)propan-2-ol
2-(tert-butyl)-1-(2-chlorophenyl)-3-1H-(1,2,4-triazol-1-yl)propan-2-ol
and/or hexaconazole or metconazole.
6. Composition or concentrate for the preservation of wood and derived
timber products according to one or more of Claims 2 to 5, character-
ized in that it comprises at least one azole in concentrations of 0.1 to
50 % by weight, preferably of 0.5 to 25 % by weight.
7. Wood preservative according to one or more of Claims 1 to 5, character-
ized in that it comprises, as additional insecticide, chlorpyrifos, phoxim,
silafluofen, cyfluthrin, cypermethrin, deltamethrin, permethrin,
imidacloprid, hexaflumuron and/or lindane.
8. Composition for the preservation of wood and derived timber products
according to one or more of Claims 1 to 7, characterized in that the
composition (ready-to-use composition) comprises 0.2 to 3 % by weight
of the fungicide, 0.005 to 1 % by weight, preferably 0.01 to 0.5 % by
weight, of the insecticide and at least one organochemical solvent or
solvent mixture and/or an oily or oil-type organochemical solvent or
solvent mixture of low volatility and/or a polar organochemical solvent

- 20 -
or solvent mixture and/or water and emulsifier and/or wetting agent and,
if appropriate, 0 to 5 % by weight, preferably 0.1 to 3 % by weight, of
fixative and/or other additives as the remainder.
9. Concentrate for the preservation of wood and derived timber products
according to one or more of Claims 1 to 7, characterized in that the
concentrate comprises 0.2 to 25 % by weight, preferably 3 to 8 % by
weight, of the fungicide, 0.05 to 5 % by weight, preferably 0.5 to 1 % by
weight, of the insecticide, 5 to 40 % by weight, preferably 10 to 30 % by
weight (calculated as solids) of at least one organochemical binder
and/or fixative or plasticizer and additionally an organochemical solvent
or solvent mixture and/or an oily or oil-type organochemical solvent or
solvent mixture of low volatility and/or a polar organochemical solvent
or solvent mixture and/or a penetrant and/or water and an emulsifier
and/or wetting agent as the remainder.
10. Process for the preservation of wood and derived timber products, char-
acterized in that a composition according to Claims 1 to 9 is applied to
the wood or the derived timber products, or the wood or the derived
timber products are treated with the compositions.
11. Use of the compositions according to Claims 1 to 9 for the preservation
of wood and derived timber products.

Description

Note: Descriptions are shown in the official language in which they were submitted.


; 3 ~
~ Le A 30 ~93-PCT - l -
.L~ `; ^J &.~
T~ T~ L~rTl
T~CP~ ive c~ kin~tiQn~
The present application relates to new active combinations which are com-
posed, on the one hand, of ~linulllulull, which is known, and, on the other
S hand, of other known active compounds, and which are highly suitable for the
protection of industrial materials.
It is already known that ~linulllul~ has insecticidal properties.
It is furthermore known that triflumuron can be employed as active compound
against wood-destroying insects (Holz-Zentralbiatt ~L, 524 (1984).
However, wood l~lGS~lv~tiv~ must meet requirements which exceed a mere
inc~ctir~ activity.
It was therefore the aim and object of the present invention to flnd a wood
preservative which is highly effective against wood-damaging insects, in par-
ticular against wood-destroying longhorn beetles (Cerambycidae, Lyctidae,
Bostrychidae and Anobiidae) including termites and against wood-discolouring
and wood-destroying fungi and which has a good long-term action, the efficacy
of the incectici~1e not being adversely affected by the fungicide, and vice versa.
Moreover, the wood ~ v~Liv~ should have good penetration behaviour
towards the wood and the derived timber product and have a markedly lower
vapour pressure compared with the pyrethroids of the prior art.
It was found according to the invention that these aims and objects are met by
a composition or concentrate for the preservation of wood and derived timber
products which comprises 0.01 to 25 % by weight of triflumuron as a mixture
of 0.1 to 99.9 % by weight with at least one fungicide and preferably over 40 %
by weight of a mixture of solvent and/or diluent and/ or organochemical binder

~18~
and/or fixative, processingauxiliary, colorant, pigment, colorant mixture and/orpigment mixture.
Fungicides which are preferred as components in the mixtures are:
Triazoles, such as:
amitrole, azocyclotin, BAS 480F, bitertanol, difenoconazole, fenbuconazole,
fenchlorazole, fenethanil, fluquinconazole, flusilazole, flutriafol,
imibenconazole, isazofos, myclobutanil, opus, paclobutrazol, penconazole,
propioconazole, (+)-cis-1-(4-chlorophenyl)-2-(lH-1,2,4-triazol-1-yl)-cyclo-
heptanol, t~llacullazole~ triadimefon, triadimenol, triapenthenol, triflumizole,uniconazole, hexaconazole;
Azaconazole:
1- {[2-(2,4-dichlorophenyl)- 1,3-dioxolan-2-yl]methyl}1-H- 1,2,4-triazoles
Propiconazole:
1- [2-(2,4-dichlorophenyl)-4-propyl- 1,3-dioxolan-2-yl]methyl- I-H- 1,2,4-
tri~zoles
Tebuconazole:
I -p-chlorophenyl-4,4-dimethyl-3(1H- 1,2,4-triazol- 1-yl-methyl)pentan-3-ol
Cyproconazole:
2-(4-chlorophenyl)-3-cyclopropyl-1-(lH-1,2,4-triazol-1-yl)butan-2-ol
2-(1-chloro-cyclopropyl)-1-(2-chloio~ .yl)-3-(lH-1,2,4-triazol-lyl)propan-
2-ol
2- (tert-butyl)- I - (2- chlorophenyl)- 3- ( I H- I ,2,4-triazol- 1 -yl)propan-2-ol
Metconazole:
5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(lH-1,2,4-triazol-1-yl-


21 855S6
3methyl)cyclopentanol
Imidazoles, such as: - -
imazalil, p~ul~va~e, prochloraz, triflumizole, 2-(1-tert-butyl)-1-(2-chloro-
S phenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol, thiazolecarbn~nili~, such as
2',6'-dibromo-2-methyl-4-trifluoromethoxy-4'-trifluoromethyl- 1,3-thiazole-
S-carb~ nili~1~c
Copper salts, such as:
copper, copper sulphate, copper carbonate, copper llydlu~y~ hùllate, copper
chloride, copper ammonia complexes, copper amine complexes.
Zinc salts, such as:
zinc sulphate, zinc carbonate, zinc chloride.
Mixed salts, such as:
copper/boron mixtures, copper/chromium/boron mixtures,
copper/chromium/arsenic mixtures.
(E)-Methyl 2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl-3-methoxy-
acrylates,
(E)-methyl 2-[2-[6(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-
3- methoxyacrylates,
(E)-methyl 2-[2-[6-(2-fluorophenoxypyrimidin-4-yloxy]phenyl]-3-methoxy-
acrylates,
(E)-methyl 2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-
3-methoxyacrylates,
(E)-methyl 2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylates,
(E)-methyl 2-[2-[3-(5-m~lllyl~ylil~,idin-2-yloxy)phenoxy]phenyl]-3-methoxy-
acrylates,
(E)-methyl2-[2-[3-(phenyl-sulphonyloxy)phenoxy]phenyl]-3-rnetho~yacrylates,
(E)- methyl 2- [2- [3- [4-nitrophenoxy]phenoxy]phenyl]3-methoxyacrylates,
(E)-methyl 2-[2-phenoxyphenyl]-3-methoxyacrylates,

-2t8555~
- - 4 -
(E)-methyl 2-[2-[3,5-dim~L~lyL~ ,yl)pyrrol-l-yl]-3-methoxyacrylates,
(E)-methyl 2-[2-[3-methoxyphenoxy)phenyl]-3-methoxyacrylates,
(E)-methyl 2-[2-[2-phenylethen-1-yl)phenyl]-3-methoxyacrylates,
(E)-methyl 2-(2-[3,5-dichlorophenoxy]pyridin-3-yl)-3-methoxyacrylates,
(E)-methyl 2-(2-(3-(1,1,2,2-etrafluoroethoxy)phenoxy)phenyl)-3-methoxy-
acrylates,
(E)-methyl 2-(2-[3-(o~-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylates,
(E)-methyl 2-(2-(4-phenoxypyridin-1-yloxy)phenyl)-3-methoxyacrylates,
(E)-methyl 2-[2-(3-n-propyloxyphenoxy)phenyl]-3-metho~ya~ilylales,
(E)-methyl 2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methoxyacrylates,
(E)-methyl 2-[2-[3-(2-duorophenoxy)phen~l~y]~ yl-3-methoxyacrylates,
(E)-methyl 2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylates,
(E)-methyl 2-[2-(4-tert-butylpyridin-2-yloxy)phenyl]-3-methoxyacrylates,
(E)-methyl 2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylates,
IS (E)-methyl 2-[2-(3-methylpyridin-2-yloxymethyl)phenyl]-3-methoxyacrylates,
(E)-methyl 2-[2-[6(2-emthylphenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxy-
acrylates,
(E)-methyl 2-[2-(5-bromopyridin-2-yloxymethyl)phenyl]-3-methoxyacrylates,
(E)-methyl 2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxy-
acrylates,
(E)-methyl 2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-
3-methoxyacrylates,
(E),(E)-methyl 2- [2-(5,6-dim~ lpy.a~...-2-ylmethyloximinomethyl)phenyl]-
3- methoxyacrylates,
(E)-methyl 2-(2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}
3- methoxyacrylates,
(E),(E)-methyl 2- {2-(3-methoxyphenyl)methyloximinomethyl]phenyl}-
3- methoxyacrylates,
(E)-methyl 2-{2-[6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}3-methoxy-
acrylates,
(E),(E)-methyl 2- {2- [6-phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}
3-methoxyacrylates,
(E), (E)- methyl 2- ~2- [(4- ch lorophenyl)- methyloximinomethyl]phenyl }-

21 85556
- 5- -
3- methoxyacrylates,
(E)- methyl 2- {2- [6- (2- n-propylphenoxy)- 1, 3, S-triazin- 4-yloxy]phenyl~
3-methoxyacrylates,
(E),(E)-methyl2-{2-[(3-~ yl)m~lllyll,~;ll,;"omethyl]phenyl}3-methoxy-
acrylates.
Succinate dehydrogenase inhibitors, such as:
fenfuram, furcarbanil, cyclafiuramid, furmecyclox, seedvax, metsulfova~, pyro-
carbolid, oxycarboxin, shirlan, mebenil (mepronil), benodanil, flutolanil
(Moncut)
Napthalene derivatives, such as:
terbinafine, naftifine, butenafme, 3-chloro-7-(2-a~a-2,7,7-trimethyl-oct-3-en-
5-ine)
SlllfenAmi~ e such as ~ hlorflllAni~l, tolyl_uanid, folpet, fluorfolpet; captan,captofol,
Ben7imillA7.nles, such as carbendazim, benomyl, furathiocarb, fuberidazole,
thiophonat-methyl, thiabendazole or their salts;
Thiocyanates, such as thiocyanatomethylthioben70thiA701e, methylenebisthio-
cyanate;
Quaternary ammonium compounds such as benzyldimethyltetradecyl-
ammonium chloride, benzyldimethldodecylammonium chloride, didecyldi-
methylammonium chloride,
Morpholine ~1 ;va~iYt:~, such as tridemorph, fenpropimorph, falimorph,
dimethomorph, dodemorph; aldimorph, fenpropidin and their arylsulphonates,
such as, for example, p-toluenesulphonic acid and p-dodecylphenyl-sulphonic
acid,

- 6 -
Iodine derivatives, such as diiodomethyl-p-tolyl sulphone, 3-iodo-2-propinyl
alcohol, 4-chlorophenyl-3-iodop.~,~dl~yl formal, 3-bromo-2,3-diiodo-
2-propenyl ethyl carbamate, 2,3,3-triiodoallyl alcohol, 3-bromo-2,3-diiodo-
2-propenyl alcohol, 6-iodo-3-oxo-hex-5-in-ol butylcarbamate, 6-iodo-3-oxo-
S hex-5-in-ol phenylc~.l.all.dl~, 3-iodo-2-propinyl n-hexylcarbamate, 3-iodo-2-propinyl cyclohexylcarbamate, 3-iodo-2-propinyl phenylcarbamate, 3-iodo-
2-propinyly n-butylcarbamate;
Phenol derivatives, such as tribromophenol, tetrachlorophenol, 3-methyl-
4-chlorophenyl, dichlorophen, o-phenylphenol, m-phenylphenol, p-phenyl-
phenol, 2-benzyl-4-chlorophenol;
G lutaraldehyde;
bromine derivatives, such as 2-bromo-2-nitro-1,3-propanediol;
Isothiazolinones, such as N-~ .}lyli~ul}liazolin-3-one, 5-chloro-N-methyl-
isothiazolin-3-one, 4,5-dichloro-N-octyliso-thiazolin-3-one, N-octyl-
isothiazolin-3-one;
Benzisothiazolinones, 4,5-trimethylene-isothiazolinones;
Pyridines or pyrimidines, such as 1-hydroxy-2-pyridinethione (and their Na,
Fe, Mn and Zn salts), tetrachloro-4-methylsulphullyl~ ,e, pyrimethanil,
mepanipyrim, dipyrithione,
Metal soaps, such as tin napthenoate, tin octoate, tin 2-ethylhexanoate, tin
oleate, tin phosphate, tin benzoate, copper naphthenate, copper octoate,
copper 2-ethylhexanoate, copper oleate, copper phosphate, copper benzoate,
zinc naphthenate, zinc octoate, zinc 2-ethylhexanoate, zinc oleate, zinc phos-
phate and zinc benzoate;
Oxides, such as tributyltin oxide, Cu2O, CuO, ZnO;

- 7 -
Dialkyldithiocarbamates, such as Na and Zn salts of dialkyl-dithiocall.all,ates,tetramethylthiuram fliclllrhitlP;
Dithiocarbamates, cufraneb, ferbam, mancopper, mancozeb, maneb, metam,
metiram, thiram zineb, ziram;
Nitriles, such as 2,4,5,6-tetrachloroisorhthSIl- ~linitrile, 2,3,5,6-tetrafluoro-
terephthalodinitrile;
Benzothiazoles, such as 2-mercaptobenzothiazole;
Quinolines, such as 8-hydroxyquinoline, and their Cu salts;
Ben7~miflec, such as 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamides
(~D-563);
Boron compounds, such as boric acid, borates, borax;
Formaldehyde and formaldehyde-releasing compounds, such as benzyl alcohol
mono(poly)-hPmiform:-l oxazolidines, hexa-hydro-S-triazines, N-methylol-
chloro~et~mi-lP, paraformaldehyde, nitropyrin, oxolinic acid, tecloftalam;
Tris-N-(cyclohexyl~ 7Pnillmdioxy)-~lllminillm, N-(cyclo-hexy~ 7pnillm
dioxy)-tributyltin or K salts, bis-N-(cyclohexyl~ 7Pni--mdioxy)-copper.
Other fungicidal components in the mixtures which a}e very particularly pre-
ferred are:
Azaconazole, bromuconazole, ~,y~ colla~;~lle, dichlobutrazol, diniconazole,
hexaconazole, metaconazole, penconazole, propiconazole, tebuconazole, (E)-
methyl methoximino[o~-(o-tolyloxy)-o-tolyl)]acetate, (E)-rnethyl 2- ~2-[6-
(2-cyanophenoxy)-pyrimidin-4-yl-oxy]phenyl}-3-methoxyacrylate,
methfuroxam, carboxin, fenpiclonil, 4(2,2-difluoro-1,3-benzodioxol-4-yl)-lH-

21 8~5~6
.
-- 8 --
pyrrol-3-carbonitrile, butenafine and/or 3-iodo-2-propinyl-n-butylcarbamate.
Highly effective mixtures are furthermore also prepared with the following
active compounds: -
s

Fungicides
acypetacs, 2-aminobutane, ~ ulJ~lrus, anilazine, benalaxyl, bupirimate,
quinomethionate, chloroneb, chlozolinate, cymoxanil, dazomet, diclomezine,
dichloram, diethofencarb, dimethirimol, dinocab, dithianone, dodine,
drazoxolon, e~iif~nrhoc~ ethirimol, etridiazole, fenarimol, fenitropan, fentm
acetate, fentin hydroxide, ferimzone, flll~7ins~m fiuromide, flllelllf~nni~,
flutriafol, fosetyl, fthalide, furalaxyl, guazatine, hyrnexazol, iprobenfos,
iprodione, isoprothiolane, metalaxyl, meth~elllfocarb, nitrothal-isopropyl,
nuarimol, ofurace, oxadiyl, p~;lnula~ua~ pencycuron, phosdiphen, pimaricin,
piperalin, procymidone, propamocarb, propineb, pyrazophos, pyrifenox,
pyroquilone, ~IUill~02~.lC, tar oils, tecnazene, thicyofen, thiophanate-methyl,
tolclofos-methyl, triazoxide, Iri-~hl~mitl.-, tricyclazole, triforme, vinclozolin.
If au,ulu,uliàle, the following msecticides are ~ litions~lly admixed to achieveeven higher activities agamst wood-destroying insects.
Phosphoric esters, such as azinphos-ethyl, azinphos-methyl, a-1(4-chloro-
phenyl)-4-(O-ethyl, S-propyl)phosphoryloxy-pyrazole, chloropyrifos,
coumaphos, demeton, demeton-S-methyl, diazinone, dichlorvos, dimethoate,
ethoate, ethoprophos, etrimfos, fenitrothion, fenthion, heptenophos, parathion,
parathion-methl, phosalone, phoxim, pirimiphos-ethyl, pirimiphos-methyl,
profenofosm prothiofos, sulfprofos, triazophos and trichlorphon;
Carbamates, such as aldicarb, bendiocarb, a-2-(1-m~Ll.yl,ulu~yl)-phenyl
methylcarbamate, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbo-
sulfan, cloethocarb, i~u~lucal~, methomyl, oxamyl, pirimicarb, promecarb,
propoxur and thiodicarb;

21 8555~
g
Organosilicon compounds, preferably dimethyl(phenyl)silyl-methyl 3-phenoy-
benzyl ethers, such as dimethyl-(4-ethoxyphenyl)-silylmethyl 3-phenoxybenzyl
ether, or - -
S (Dim~Ll-yl~ c.,yl)-silyl-methyl 2-phenoxy-6-pyridylmethyl ethers, such as, for
example, dimethyl(9-ethoxy-phenyl)-silylmethyl 2-phenoxy-6-pyridylmethyl
ether or [(phenyl)-3-(3-phenoxyphenyl)-propyl](dimethyl)-silames, such as, for
example, (4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxyphenyl-propyl]dimethyl-
silane, silafluofin
Pyrethroids, such as allethrm, Alrh~m~Pthrin, bioresmethrin, byfenthrin, cyclo-
prothrin, cyfluthrin, decamethrm, cyhalothrin, cypermethrin, deltamethrin,
alpha-cyano-3--phenyl-2-methylbenzyl 2,2-dimethyl-3-(2-chloro-2-trifluoro-
methylvinyl)cyclopropanecarboxylate, f~ V~dtlll~l, fenfluthrin, fenvalerate,
flucythrinate, flumethrin, fluv-dlinate, permethrin, resmethrin and tralomethrin;
Nitroimines and nitromethylenes, such as 1-[(6-chloro-3-pyridinyl)-methyl]-
4,5-dihydro-N-nitro-lH-imidazole-2-amine (imi~ rrid), N-[(6-chloro-3-
pyridyl)methyl-]N2cyano-N~-methyls~Pt:~mi-lP (Nl-25),
Abamectm, AC 303,630, acephate, acrinathrin, alanycarb, aldoxycarb, aldrin,
ammonium bifluorides, amitraz, azamethiphos, Bacillus thuringiensis, phosmet,
phosphamidon, phosphine, prallethrin, propaphos, ~Ivp~ pl-os, prothoate,
pyraclofos, pyrethrins, pyridaben, pyridafenthion, pyriproxyfen, quinalphos,
RH-7988, rotenone, sodium fluorides, sodium hexafluorosilicates, sulfotep,
sulphuryl fluorides, tar oils, t~nubcll~u~ , tefluthrin, temephos, terbufos, tetra-
chlorvinphos, tetramethrin, 0-2-tert-butyl-pyrimidin-5-yl-o-isopropyl
phosphorothiates, thiocyclam, thiofanox, thiometon, tralomethrin, triflumuron,
trimethacarb, vamidothion, verticillium lacanii, XMC, xylylcarb, benfuracarb,
bensultap, bifenthrin, bioallethrin, MERbioallethrin (S)-cyclopentenyl isomer,
bromophos, bromophos-ethyl, buprofezin, cadusafos, calcium polysulfides,
carbophenothion, cartap, qumomethionate, chlordane, chlorfenvinphos,
chlorfluazuron, chlormephos, chloropicrin, chloropyrifos, cyanophos, beta-

7 ~
- 10 -
cyfluthrin, alpha-cypc~.l.cll..--., cyophenothrm, cyromazine, dazomet, DDT,
demeton-S-methylsulphone, diafenthiuron, dialifos, dicrotophos,
diflubenzuron, dinoseb, ~ )fos~ diaxacarb, disulfoton, DNOC,
empenthrin, endo~llfAn, EPN, esfenvalerate, ethiofencarb, ethion, etofenprox,
fenobucarb, fenoxycarb, fensulfothion, fipronil, flucycloxuron, nu~llpl o~,
flufenoxuron, fonofos, formetanate, formothion, fosmethilan, furathiocarb,
heptachlor, hu~u-lluluil, hydramethylnon, hydrogen cyanides, hydroprene,
IPSP, isazofos, isofenphos, isoprothiolane, isn~Athinn, iodfenphos, kadethrim,
lindane, mAlAfhinn, mecarbam, mephosfolan, mercurous, chlorides, metam,
metarthizium, anisopliae, methacrifos, mPthAmidophos, m~PfhidAthion; methio-
carb, methoprene, methoxychlor, methyl isothiocyanates, metho~carb,
mevinphos, monocrotophos, naled, neodiprion sertifer NPV, nicotines,
omethoate, oxydemeton-methyl, pentachlorophenol, petroleum oils,
phenothrm, phenthoate, phorate;
Benzoylureas, such as chlu.nu~uluil, diflllhpn7llron~ flufenoxuron,
flucycloxuron, hexaflumuron, penfluron, teflubenzuron, other development
inhibitors, such as, for example, [2-benzoyl-1-(1,1-dimethylethyl)]-
benzohydrazide, 2,6-dimethoxy-N-[5-]4-(pentafluoroethoxy)-phenyl-[2,3,4-
thiadiazol-2-yl]-~Pn7AmidP. N-cyclopropyl-1,3,5-triazine-2,4-triamine,
2-(4-phenoxyphenoxy)-ethyl ethylcarbamate, 1-(decycloxy)-4-[(6-methoxy-
4-hexinyl)-oxy]benzene, (2-propinyl) 4-methoxy-benzoate, fenoxycarb,
pyriproxyfen, triarathene, thiapronil, hex~vthiazox, clofentezine, 4-chloro-
5-(6-chloro-3-pyridylmethoxy)-2-(3,4-dichlorophenyl)-pyridazin-3(2H)-ones,
buprofezin, hydroprene, kinoprene, methoprene, cycloprate, gusathm, padan,
paraxon, tribunil, isomers and triprenes.
Synergistic effects are observed when the mixtures of triflumuron, at least one
fungicide and, if a~lv~ Le~ other fungicides or else in~cfil i~iP~ are mixed
with each other m certam ratios.
The weight ratios of the active compounds can be varied ~vithin a relatively
wide range, the weight ratio of llinulllulull to the fungicide, or fungicides,

2~ ~55~
11 -
preferably being 1:20,000 to 1:10, in particular 1:10,000 to 1:100.
Surprisingly, these active combinations have a particularly potent in~Pcti~
action against wood-destroying insects, combined with a broad fungicidal and
S bactericidal action against microorganisms which are relevant in the protection
of materials.
The following wood-destroying insects may be mentioned by way of example
but without limifslti-~n:
Beetles
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium
rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis,
Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus
linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus
spec. Tryptodendron spec. Apate monachus, Bostrychus capucms,
Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus
Dermapterans
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur
Termites
Kalotermes flavicollis, Cryptotermers brevis, Heterotermes indicola,
RPti~ulitPrmes flavipes, Reti~l-litPrmes santonensis, Reti~nllitPrmes lucilugus,Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
The following groups of microorganisms may be mentioned by way of example
but without limit~ti~-n: -
A: Wood-discolouring fungi:

21 8~556
- 12-
Al: A~ollly~
Ceratocystis, such as Certocystis minor
A2: Dcu~ ly-;etes:
Aspergillus, such as Aspergillus niger
Aul~ ob~;~liulll, such as Aul._obas~;liulll pullulans
Dactylium, such as Dactylium fusarioides
Penicillium, such as Penicillium brevicaule or
Penicillium variabile
Sclerophoma, such as Sclerophoma pithyophila
Scopularia, such as Scopularia phycomyces
Trichoderma, such as Trichoderma viride or
Trichoderma lignorum
A3: Zygomycetes:
Mucor, such as Mucor spinorus
B: Wood-destroying fungi:
Bl: Ascomycetes:
Chaetomium, such as Chaetomium globosum or
Chaetomium alba-arenulum
Humicola, such as Humicola g~isea
Petriella, such as Petriella setifera
Trichurus, such as Trichurus spiralis
B2: Basidiomycetes:
Coniophora, such as Coniophora puteana
Coriolus, such as Coriolus versicolor
Donkioporia, such as Donkioporia expansa
Glenospora, such as Glenospora graphii
Gloeophyllum, such as Gloeophyllum abietinum or
Gloeophy~lum adoratum or Gl. protactum or

~1 85556
- 13 -
Glo~ol,l.yllulll sepiarium or Gl. trabeum
Lentirlus, such as Lentinus cyathiformes or
Lentinus edodes, such as Lentinus lepideus or
Lentinus grinus or L. squarrolosus
Paxillus, such as Paxillus panuoides
Pleurotus, such as Pleurotus ostreatus
Poria, such as Poria monticola or Poria placenta or
Poria vaillantii or Poria vaporaria
Serpula, such as Serpula llil..al.~oid~ or Serpula lacrymans
Stereum, such as Stereum hirsutum
Tyromyces, such as Tyromyces palustris
B3: Deuteromycetes
Alternaria, such as Alternaria tenius
Cladosporium, such as Clasdosporium herbarum
The active compound mixture can be used as such, m the form of concentrates
or generally customary forrn~ ti~-n~ such as powders, granules, solutions,
suspensions, emulsions or pastes, to prepare a ready-to-use wood ,UI~ dLive,
if d,UIUlUIJI idl~ by simply diluting it with water.
The abovementioned compositions or concentrates can be prepared in a man-
ner known per se, for example by mi?.~ing the active compounds with at least
one solvent or diluent, emulsifier, dispersant and/or binder or fi.?~ative, water
repellent? if ~,ululul;ale desiccants and UV stabilizers and if d~ UIUlid~e
colorants and pigments and other processmg âuxiliaries.
The solvent and/or diluent used is an organochemical solvent or solvent mix-
ture and/or an oily or oil-type organochemical solvent or solvent mixture of lowvolatility and/or a polar organochemical solvent or solvent~mixture and/or
water in combination with at least one emulsifier and/or wetting agent.

2~85~5~
- 14-
Organochemical solvents which are employed are preferably oily or oil-type
solvents which have an eva~lUId~iUII number of above 35 and a flash point of
above 30~C, preferably above 45~C. Such wdter-insoluble, oily and oil-type
solvents of low volatility are suitable mineral oils or their aromatic fractions or
mineral oil-comprising solvent mixtures, preferably white spirit, petroleum
and/or alkyl benzene.
Mineral oils with a boiling range of 170 to 220C, white spirit with a boiling
range of 170 to 220C, spmdle oil with a boiling range of 250 to 350C, petro-
leum or aromatics with a boiling range of 160 to 280C, oil of ~UlU~ UlC and
the like are advantageously used.
In a preferred embodiment, liquid aliphatic lly-Lu.,albOlls with a boilmg range
of 180 to 210C or high-boiling mixtures of aromatic and aliphatic hydrocar-
bons with a boiling range of 180 to 220C and/or spindle oil and/or mono-
chloronaphthalene, preferably a-monochloron~rhthsllpne~ are used.
Pdrt of the organic oily or oil-type solvents of low volatility with an evaporation
number of above 35 and a flash point of above 30C, preferably above 45~C, can
be replaced by organochemical solvents of high or medium volatility, with the
proviso that the solvent mixture also has an evaporation number of above 35
and a flash point of above 30aC, preferably above 45CC, and that the insecti-
cide/fungicide mixture is soluble or emulsifiable in this solvent mixture.
In a preferred embodiment, part of the organochemical solvent or solvent
mixture or an aliphatic polar organochemical solvent or solvent mixture is
replaced. Solvents which are preferably used are aliphatic organochemical
solvents which contain hydroxyl and/or ester and/or ether groups, such as, for
example, glycol ethers, esters or the like.
Orgdnochemical binders which are used within the scope of the present inven-
tion are the bindmg drying oils and/or synthetic resins which are known per se
and can be diluted in water and/or dissolved or dispersel or emulsified in the

21 85556
- 15 -
organochemical solvents employed, in particular binders composed of, or
comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate,
polyester resin, polycon~l~nc~til~n or polyaddition resin, polyurethane resin,
alkyd resin or modified alkyd resm, phenol resin, l~ydluc~lJu-l resin, such as
S indene-coumarone resin, silicone resin, drying vegetable and/or drying oilsand/or physically drying binders bagd on a natural and/or synthetic resin.
The synthetic resin used as binder can be employed in the form of an emulsion,
dispersion or solution. Other bmders which can be used are bitumen or bitumi-
nous substances in amounts of up to 10 % by weight. Colorants, pigments,
water repellents, odour-masking C~l~st~nc~c and inhibitors or allti~,UllVi~ , all
of which are known per se, and similar substances can ~ lition~lly be used.
The composition or con~rntr~t~ preferably comprises, according to the inven-
tion, at least one alkyd resin or modified alkyd resin and/or a drying vegetableoil as the organochemical binder. Preferably used according to the invention arealkyd resins with an oil content of over 45 % by weight, preferably 50 to 68 %
by weight.
All or part of the abovementioned binder can be replaced by a f xative (mixture)or a plasticizer (mixture). These additives are intended to prevent volAtili7~ti--n
of the active compounds and crystSIlli7~ti~-n or ,~,,~.,il,i~ioll. They preferably
replace 0.01 to 30 % of the binder (based on 100 % of the binder employed).
The plasticizers are from the chemical classes of the phthalic esters, such as
dibutyl phthalate, dioctyl phthalate or ben7yl butyl phthalate, phosphoric esters,
such as tributyl phosphate, adipic esters, such as di-(2-ethylhexyl) adipate,
stearates, such as butyl stearate or amyl stearate, oleates, such æ butyl oleate,
glycerol ethers or higher-molecular-weight glycol ethers, glycerol esters and
p-toluenesulphonic esters.
Fixatives are based chemically on polyvinyl alkyl ethers, such as, for example,
polyvinyl methyl ether, or ketones, such æ benzophenone and ethylenebenzo-


~18~
- 16-
phenone, or are based on amines, sueh as alkanolamines, in particular monoet-
hanolamine, or else ammonia.
Also partieularly suitable as solvent or diluent is water, if dy~ idL~ as a
S mixture with one or more of the abovementioned organochemical solvents or
diluents, .~nnllIcifi~rs and ~ ~"l~
Exdmples of wood which can be protected by the composition according to the
invention or mixtures comprismg it are to be understood as meaning: construc-
tion timber, wooden beams, railway sleepers, bridge components, jetties,
wooden vehicles, boxes, pallets, cont~iner~, telephone poles, wood laggings,
windows and doors made of wood, plywood, particleboard, joiner's work, or
wood produets whieh, quite generally, are used in eonstruetion or in joinery.
A partieularly effieient proteetion of wood is aehieved by industrial-seale
ldlion proeesses, for exdmple vaeuum proeesses, double-vacuum pro-
cesses or processes cdrried out under pressure.
The wood ~ a~ S used for the protection of wood and derived timber
products preferably comprise ~lillulllul~ at a concentration of 0.001 to 3 % by
weight and the fungicide, or fungicides, at a concentration of 0.1 to 10 % by
weight.
Preferred CIJlllp~ ,lls (ready-to-use compositions) preferably comprise 0.2 to
3 % by weight of the fungicide, 0.005 to 1 % by weight, preferably 0.01 to
0.5 % by weight, of ~lillul~lul~ll, if d~ plidle in combination with a further
insecticide, in particular cyfluthrin, and at least one organochemical solvent or
solvent mixture and/or an oily or oil-type orgdnochemical solvent or solvent
mixture of low volatility and/or a polar organochemical solvent or solvent
mixture and/or water and emulsifier and/or wetting agent and, if appropriate,
0 to 5 % by weight, preferably 0.1 to 3 % by weight, of fixdtive and/or other
additives as the remainder.

2~ 8555b
- 17 -
Particularly preferred (ready-to-use) compositions comprise 2 to 30 % by
weight, preferably S to 22 % by weight, calculated as solids, of a synthetic resin
binder, preferably an allcyd resin and/or a drying vegetable oil and at least one
organochemical solvent or solvent mixture and/or an oily or oil-type organo-
chemical solvent or solvent mixture of low volatility and/or a polar organo-
chemical solvent or solvent mixture and/ or water and emulsifier and/or wetting
agent and, if ~,U,u~u~Jl;dte~ d~ c~nt~ colourants, pi~ments, anti-settlingagentsand/or UV stabilizers as the remainder.
Concentrates for the preservation of wood and derived timber products prefer-
ably comprise 0.2 to 25 % by weight, preferably 3 to 8 % by weight, of the
fungicide, O.OS to 5 % by weight, preferably O.S to 1% by weight, of
~lillulllu~ull~ if alu~lulJI;a~ in combination with a further ;".~ , 5 to 40 %
by weight, preferably 10 to 30 % by weight (calculated as solids) of at least one
organochemical binder and/or fixative or plasticizer and a~1~litir n:~1ly an organo-
chemical solvent or solvent mixture and/or an oily or oil-type organochemical
solvent or solvent mixture of low volatility and/or a polar organochemical
solvent or solvent mixture and/or a penetrant and/or water and an emulsifier
and/or wetting agent as the remainder.
The amount of the compositions or concentrates employed depends on the
species and the occurrence of the insects, microorganisms, the microbial count
and on the medium. Upon use, the optimum amount can be determined in
each case by test series. In general, however, it is suffcient to employ 0.001 to
20 % by weight, preferably 0.05 to 10 % by weight, of the active compound
mixture, based on the material to be protected.
The compositions according to the invention allow to replace the insecticidal
compositions of the prior art in an advantageous manner by more effective
ones. They exhibit good stability and advantageously have a broad spectrum of
action.

Representative Drawing

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date Unavailable
(86) PCT Filing Date 1995-03-06
(87) PCT Publication Date 1995-09-21
(85) National Entry 1996-09-13
Dead Application 1999-03-08

Abandonment History

Abandonment Date Reason Reinstatement Date
1998-03-06 FAILURE TO PAY APPLICATION MAINTENANCE FEE

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $0.00 1996-09-13
Registration of a document - section 124 $0.00 1996-12-12
Maintenance Fee - Application - New Act 2 1997-03-06 $100.00 1997-02-12
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
BAYER AKTIENGESELLSCHAFT
Past Owners on Record
BUSCHHAUS, HANS-ULRICH
KUGLER, MARTIN
KUNISCH, FRANZ
UHR, HERMANN
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Cover Page 1996-12-30 1 14
Description 1995-09-21 17 519
Claims 1995-09-21 3 77
Abstract 1995-09-21 1 7
International Preliminary Examination Report 1996-09-13 40 1,471
Fees 1997-02-12 1 51