U.S. patent application number 11/932337 was filed with the patent office on 2008-02-21 for microbicidal compositions.
Invention is credited to HANS-ULRICH BUSCHHAUS, LUTZ HEUER, MARTIN KUGLER, MICHAEL SCHWAMBORN, PETER WACHTLER.
Application Number | 20080044492 11/932337 |
Document ID | / |
Family ID | 6469595 |
Filed Date | 2008-02-21 |
United States Patent
Application |
20080044492 |
Kind Code |
A1 |
HEUER; LUTZ ; et
al. |
February 21, 2008 |
MICROBICIDAL COMPOSITIONS
Abstract
There are described the use of
.alpha.-(4-chlorophenyl)-.alpha.-(1-cyclopropylethyl)-1H-1,2,4-triazole-1-
-ethanol as a microbicide for the protection of industrial
materials, and compositions containing this compound.
Inventors: |
HEUER; LUTZ; (Krefeld,
DE) ; WACHTLER; PETER; (Koln, DE) ;
SCHWAMBORN; MICHAEL; (Koln, DE) ; KUGLER; MARTIN;
(Leichlingen, DE) ; BUSCHHAUS; HANS-ULRICH;
(Krefeld, DE) |
Correspondence
Address: |
NORRIS, MCLAUGHLIN & MARCUS, PA
875 THIRD AVENUE
18TH FLOOR
NEW YORK
NY
10022
US
|
Family ID: |
6469595 |
Appl. No.: |
11/932337 |
Filed: |
October 31, 2007 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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08888609 |
Jul 7, 1997 |
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11932337 |
Oct 31, 2007 |
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08542566 |
Oct 13, 1995 |
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08888609 |
Jul 7, 1997 |
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08338356 |
Nov 14, 1994 |
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08542566 |
Oct 13, 1995 |
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08128450 |
Sep 28, 1993 |
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08338356 |
Nov 14, 1994 |
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Current U.S.
Class: |
424/630 ;
514/383 |
Current CPC
Class: |
A01N 43/653 20130101;
B27K 3/50 20130101; B27K 3/343 20130101; B27K 3/34 20130101; A01N
43/653 20130101; A01N 61/00 20130101; A01N 59/20 20130101; A01N
33/12 20130101; A01N 43/653 20130101; A01N 61/00 20130101; A01N
59/20 20130101; A01N 33/12 20130101; A01N 43/653 20130101; A01N
61/00 20130101; A01N 59/20 20130101; A01N 33/12 20130101; A01N
43/653 20130101; A01N 61/00 20130101; A01N 59/20 20130101; A01N
33/12 20130101; A01N 43/653 20130101; A01N 61/00 20130101; A01N
59/20 20130101; A01N 33/12 20130101; A01N 43/653 20130101; A01N
2300/00 20130101; A01N 43/653 20130101; A01N 33/12 20130101; A01N
59/20 20130101; A01N 61/00 20130101 |
Class at
Publication: |
424/630 ;
514/383 |
International
Class: |
A01N 43/653 20060101
A01N043/653; A01N 59/20 20060101 A01N059/20; A01P 1/00 20060101
A01P001/00 |
Foreign Application Data
Date |
Code |
Application Number |
Oct 5, 1992 |
DE |
P.42 33 337.7 |
Claims
1.-6. (canceled)
7. An antimicrobial composition comprising a synergistically
effective amount therefor of: a) a first ingredient, which is
.alpha.-(4-chlorophenyl)-.alpha.-(1-cyclopropylethyl)-1H-1,2,4-triazole-1-
-ethanol of the formula (I): ##STR2## (cyproconazole) or a metal
salt complex or acid addition salt thereof; and b) a second
ingredient, which is a fungicide, algicide, molluscicide or
insecticide other than said first ingredient.
8. The antimicrobial composition according to claim 7, wherein said
second ingredient is a copper compound.
9. The antimicrobial composition according to claim 7, wherein said
second ingredient is an azole fungicide or insecticide other than
said first ingredient.
10. A method of protecting an industrial material against the
deleterious effects of microorganisms, said method comprising
applying to said industrial material an amount of the antimicrobial
composition according to claim 7 that is effective to protect said
industrial material against said microorganisms.
11. The method according to claim 10, wherein said second
ingredient is a copper compound.
12. The method according to claim 10, wherein said second
ingredient is an azole fungicide or insecticide other than said
first ingredient.
Description
[0001] The invention relates to the use of the compound
.alpha.-(4-chlorophenyl-.alpha.-(1-cyclopropyl-ethyl)-1H-1,2,4-triazole-1-
-ethanol(cyproconazole) as a microbicide for the protection of
industrial materials, and to synergistic mixtures containing this
compound.
[0002] It has been disclosed that the azole derivatives described
in DE-OS (German Published Specification) 3,406,993 can be used for
protecting plants.
[0003] The present invention relates to the use of an azole
derivative of the formula (I) ##STR1## its metal salts or acid
addition compounds as a microbicide for the protection of
industrial materials.
[0004] The azole derivate can not only be in the form of the free
base but also in the form of a metal salt complex or an acid
addition salt. Suitable metal salts are preferably salts of metals
of main groups II to IV and subgroups I and II as well as IV to VII
of the periodic table, the following being mentioned by way of
example: copper, zinc, manganese, magnesium, tin, iron, calcium,
aluminium, lead, chromium, cobalt and nickel.
[0005] Suitable anions of the salts are those which are derived,
preferably, from the following acids: hydrohalic acids such as, for
example, hydrochloric acid and hydrobromic acid, furthermore
phosphoric acid, nitric acid and sulphuric acid.
[0006] The metal salt complexes of the azole derivative can be
obtained in a simple manner by customary processes, for example by
dissolving the metal salt in alcohol, for example ethanol, and
adding the solution to the azole fungicide. Metal salt complexes
can be isolated in a known manner, for example by filtration, and,
if appropriate, purified by recrystallisation.
[0007] The following acids are preferably suitable for preparing
acid addition salts of the azole derivative: the hydrohalic acids,
such as, for example, hydrochloric acid and hydrobromic acid, in
particular hydrochloric acid, furthermore phosphoric acid, nitric
acid, sulphuric acid, mono- and bifunctional carboxylic acids and
hydroxycarboxylic acids such as, for example, acetic acid,
propionic acid, 2-ethylhexanoic acid, butyric acid, mandelic acid,
oxalic acid, succinic acid, 2-hydroxy-ethane-dicarboxylic acid,
maleic acid, fumaric acid, tartaric acid, citric acid, salicylic
acid, sorbic acid, lactic acid, as well as sulphonic acids, such
as, for example, p-toluenesulphonic acid, p-decyl phenyl sulphonic
acid, p-dodecyl phenyl sulphonic acid, 1,4-naphthalenedisulphonic
acid, alkanesulphonic acids, benzoic acid and optionally
substituted benzoic acids.
[0008] The acid addition salts of the compounds can be obtained in
a simple manner by customary salt formation methods, for example by
dissolving a compound in a suitable inert solvent and adding the
acid, for example, hydrochloric acid, and they can be isolated in a
known manner, for example by filtration, and, if appropriate,
purified by washing with an inert organic solvent.
[0009] The compound (R*,R*)
-.alpha.-(4-chlorophenyl-.alpha.-(1-cyclopropyl-ethyl)-1H-1,2,4-triazole--
1-ethanol(cyproconazole) is particularly preferred.
[0010] Surprisingly, these compounds display a particularly
powerful microbicidal, in particular fungicidal, activity against
microorganisms which are relevant in the protection of materials,
combined with a broad spectrum of action; they are active, above
all, against moulds and wood-discolouring and wood-destroying
fungi. The following groups of microorganisms may be mentioned by
way of example, but without imposing any limitation:
[0011] A: Wood-discolouring fungi: [0012] A1: Ascomycetes; [0013]
Ceratocystis such as Ceratocystis minor [0014] A2: Deuteromycetes;
[0015] Aspergillus such as Aspergillus niger [0016] Aureobasidium
such as Aureobasidium pullulans [0017] Dactylium such as Dactylium
fusarioides [0018] Penicillium such as Penicillium brevicaule or
Penicillium variabile [0019] Sclerophoma such as Sclerophoma
pithyophila [0020] Scopularia such as Scopularia phycomyces [0021]
Trichoderma such as Trichoderma viride or Trichoderma lignorum
[0022] A3: Zygomycetes: [0023] Mucor such as Mucor spinorus
[0024] B: Wood-destroying fungi: [0025] B1: Ascomycetes: [0026]
Chaetomium such as Chaetomium globosum or Chaetomium alba-arenulum
[0027] Humicola such as Humicola grisea [0028] Petriella such as
Petriella setifera [0029] Trichurus such as Trichurus spiralis
[0030] B2: Basidiomycetes [0031] Coniophora such as Coniophora
puteana [0032] Coriolus such as Coriolus versicolor [0033]
Donkioporia such as Donkioporia expansa [0034] Glenospora such as
Glenospora graphii [0035] Gloeophyllum such as Gloeophyllum
abietinum or Gloeophyllum adoratum or Gl. protactum or Gloeophyllum
sepiarium or Gl. trabeum [0036] Lentinus such as Lentinus
cyathiformes or Lentinus edodes or Lentinus lepideus or Lentinus
grinus or L. squarrolosus [0037] Paxillus such as Paxillus
panuoides [0038] Pleurotus such as Pleurotis ostreatus [0039] Poria
such as Poria monticola or Poria placenta or Poria vaillantii or
Poria vaporaria [0040] Serpula such as Serpula himantoides or
Serpula lacrymans [0041] Stereum such as Stereum hirsutum [0042]
Tyromyces such as Tyromyces palustris [0043] B3: Deuteromycetes
[0044] Alternaria such as Alternaria tenius [0045] Cladosporium
such as Cladosporium herbarum
[0046] The amount of active substance employed depends on the
species and the occurance of the microorganisms, the microbial
count and the medium. The optimum dosage rate for use can be
determined in each case by test series. In general, however, it
suffices to employ 0.001 to 20% by weight, preferably 0.05 to 10%
by weight, of the active compound based on the material to be
protected.
[0047] The active compound can be used as such, in the form of
concentrates or generally customary formulations such as powder,
granules, solutions, suspensions, emulsions or pastes.
[0048] The abovementioned formulations can be prepared in a manner
known per se, for example by mixing the active compound with at
least one solvent or diluent, emulsifier, dispersant and/or binder
or fixative, water repellant, optionally siccatives and UV
stabilisers, and optionally colourants and pigments as well as
other processing auxiliaries.
[0049] Suitable solvents or diluents are organochemical solvents or
solvent mixtures and/or a polar organic solvent or solvent mixture
and/or an oily or oil-type organochemical solvent or solvent
mixture and/or water, if appropriate together with an emulsifier
and/or wetting composition. Customary water-insoluble oily or
oil-type solvents of low volatility which are preferably used are
the particular mineral oils/mineral-oil-containing solvent mixtures
or their aromatic fractions. White spirit, petroleum or
alkylbenzenes, and additionally spindle oil and
monochloronaphthalene may be mentioned as being preferred. The
boiling ranges of these solvent (mixtures) of low volatility cover
a range of approximately 170.degree. C. to not more than
350.degree. C.
[0050] The above-described oily or oil-type solvents of low
volatility can be replaced partially by more volatile
organochemical solvents.
[0051] To prepare a wood preservative, some of the above described
solvent or solvent mixture is preferably replaced by a polar
organochemical solvent or solvent mixture. Solvents which are
preferably used are those containing hydroxyl groups, ester groups,
ether groups or mixtures of this functionality. Examples which may
be mentioned are esters or glycol ethers. Binders are to be
understood according to the invention as being synthetic resins,
binding drying oils, for example based on acrylic resins, vinyl
resins, polyester resins, polyurethane resins, alkyd resins, phenol
resins, hydrocarbon resins or silicone resins which can be diluted
with water or are soluble, dispersible or emulsifiable in
organochemical solvents. The binder used can be employed as a
solution, emulsion or dispersion. Mixtures of alkyd resins and
drying vegetable oil are preferably used. Alkyd resins with an oil
content of between 45 and 70% are particularly preferred.
[0052] All or some of the abovementioned binder can be replaced by
a fixative (mixture) or a plasticiser (mixture). These additives
are intended to prevent volitilisation of the active compound as
well as crystallisation or precipitation. They preferably replace
0.01 to 30% of the binder (based on 100% of the binder used).
[0053] The plasticisers are from the chemical classes of the
phthalic esters such as dibutyl, dioctyl or benzyl butyl phthalate,
phosphoric esters such as tributyl phosphate, adipic esters such as
di-(2-ethylhexyl)adipate, stearates such as butyl stearate and amyl
stearate, oleates such as butyl oleate, glycerol ethers or
higher-molecular-weight glycol ethers, glycerol esters as well as
p-toluenesulphonic esters.
[0054] Fixatives are based, from the chemical point of view, on
polyvinyl alkyl ethers such as, for example, polyvinyl methyl
ether, or ketones such as benzophenone or ethylenebenzophenone.
[0055] The preferred solvent or diluent is water, if appropriate in
a mixture with one or more of the abovementioned solvents or
diluents, emulsifiers and dispersants.
[0056] Industrial materials according to the invention are non-live
materials which have been prepared for use in industry. For
example, industrial materials which are intended to be protected by
the active compound from microbial change or destruction can be
glues, sizes, paper and board, textiles, leather, wood, paints and
plastic articles, cooling lubricants and other materials which can
be infested with, or decomposed by, microorganisms. Parts of
production plants, for example cooling-water circuits, which may be
impaired by the multiplication of microorganisms may also be
mentioned from amongst the materials to be protected. Preferred
industrial materials beyond the scope of the invention are glues,
sizes, paper and board, leather, wood, derived timber products,
paints, cooling lubricants, aqueous hydraulic fluids and cooling
circuits.
[0057] The active compound of the formula (I), or compositions or
concentrates containing it, are preferably employed for protecting
wood and derived timber products against microorganisms, for
example against wood-destroying or wood-discolouring fungi, in
particular in the protection of tropical wood.
[0058] Wood which can be protected by the active compound of the
formula (I) or by mixtures containing them is to be understood as
meaning, for example, structural timber, wooden beams, railway
sleepers, components of bridges, jetties, vehicles made of wood,
boxes, pallets, containers, telegraph poles, wooden fences, wooden
lagging, windows and doors made of wood, plywood, chipboard,
joinery, or wooden products which are used, quite generally, for
building houses or in building joinery.
[0059] The protection of wood is particularly effective when
large-scale impregnating treatments, for example vacuum, double
vacuum or pressure treatments, are used.
[0060] The active compound of the formula (I) is preferably mixed
with at least one other antimicrobially active substance, fungicide
and, in particular, with other active compounds, to increase the
spectrum of action or to achieve particular effects such as, for
example, an additional protection against insects. In many cases,
this results in synergistic effect, that is to say, the activity of
the mixture is greater than the activity of the individual
components. Particularly preferred components for the mixtures are,
for example, the following compounds:
[0061] Sulphenamides, such as dichlofluanid, tolylfluanid, folpet
and fluorfolpet;
[0062] Benzimidazoles, such as carbedazim, benomyl, fuberidazole,
thiabendazole or their salts;
[0063] Thiocyanataes such as thiocyanatomethylthiobenzothiazole or
methylene bis-thiocyanate; Quaternary ammonium compounds such as
benzyldimethyltetradecylammonium
[0064] chloride, benzyldimethyldodecylammonium chloride or
didecyldimethylammonium chloride;
[0065] Morpholine derivatives such as tridemorph, fenpropiomorph or
falimorph;
[0066] Azoles such as triadimefon, triadimenol, bitertanol,
tebuconazole, propioconazole, azaconazole, hexaconazole, prochloraz
or bromuconazole, metconazole, penconazole, difenoconazole,
fenbuconazole, opus, fensilazole.
[0067]
2-(2-Chlorocyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)--
propan-2-ol;
[0068] Iodine derivatives such as diiodomethyl-p-tolyl sulphone,
3-iodo-2-propinyl alcohol, 4-chlorophenyl-3-iodopropargyl formal,
3-bromo-2,3-diiodo-2-propenyl ethylcarbonate, 2,3,3-triiodoallyl
alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol,
3-iodo-2-propinyl-n-butyl carbamate, 3-iodo-2-propinyl
n-hexylcarbamate, 3-iodo-2-propinyl cyclohexylcarbamate and
3-iodo-2-propinyl phenylcarbamate;
O-1-(6-Iodo-3-oxo-hex-5-myl)butylcarbamate,
O-1-(6-Iodo-3-oxo-hex-5-inyl)phenylcarbamate, Nepcodide VP 305.
[0069] Phenol derivatives such as derivatives such as
tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol,
dichlorophen, o-phenylphenol, m-phenylphenol, p-phenylphenol or
2-benzyl-4-chlorophenol;
[0070] Bromine derivatives such as 2-bromo-2-nitro-1,3-propanediol
or 2-Brom-2-brommethyl-glutaridinitril;
[0071] Isothiazolinones such as N-methylisothiazolin-3-one,
5-chloro-N-methyl-isothiazolin-3-one,
4,5-dichloro-N-octylisothiazolin-3-one or
N-octyl-isothiazolin-3-one;
[0072] Benzoisothiazolinones or
4-5-trismethylen-N-methylisothiazol-3-on;
[0073] Pyridines such as 1-hydroxy-2-pyridinethione (and their
sodium, iron, manganese and zinc salts) or
tetrachloro-4-methylsulphonylpyridine;
[0074] Metal soaps such as tin naphthenate, tin octoate, tin
2-ethylhexanoate, tin oleate, tin phosphate, tin benzoate, copper
naphthenate, copper octoate, copper 2-ethyl-hexanoate, copper
oleate, copper phosphate, copper benzoate, zinc naphthenate, zinc
octoate, zinc 2-ethylhexanoate, zinc oleate, zinc phosphate or zinc
benzoate;
[0075] Oxides such as tributyltin oxide, Cu.sub.2O, CuO or ZnO;
[0076] Dialkyldithiocarbamataes such as sodium and zinc salts of
dialkylthiocarbamataes, tetramethylthiuram disulphide;
[0077] Nitriles such as 2,4,5,6-tetrachloroisophthalodinitrile;
[0078] Benzothiazoles such as 2-mercaptobenzothiazol;
[0079] Quinolines, such as 8-hydroxyquinoline, and their copper
salts;
[0080] Boron compounds, such as boric acid, boric esters or
borax;
[0081] Formaldehyde and formaldehyde-releasing compounds such as
benzyl alcohol mono(poly)-hemiformal, oxazolidines,
hexahydro-S-triazines, N-methylolchloroacetamide or
paraformaldehyde;
[0082] Tris-N-(cyclohexyldiazeniumdioxy)-aluminium,
N-(cyclohexyldiazeniumdioxy)-tributyltin or potassium salts
thereof, or bis-N-(cyclohexyldiazeniumdioxy)-copper.
[0083] The following are preferably added as insecticide:
[0084] Phosphoric esters such as azinphos-ethyl, azinphos-methyl,
1-(4-chlorophenyl)-4-(O-ethyl,S-propyl)phosphoryloxypyrazole,
chloropyrifos, coumaphos, demeton, demeton-S-methyl, diazinon,
dichlorvos, dimethoate, ethoprophos, etrimfos, fenitrothion,
fenthion, heptenophos, parathion, parathion-methyl, phosalone,
phoxim, pirimiphos-ethyl, pirimiphos-methyl, profenofos,
prothiofos, sulfprofos, triazophos and trichlorophon;
[0085] Carbamates such as aldicarb, bendiocarb,
2-(1-methyl-propyl)-phenyl methylcarbamate, butocarboxim,
butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb,
isoprocarb, methomyl, oxamyl, pirimicarb, promecarb, propoxur and
thiodicarb;
[0086] Organosilicon compounds, preferably
dimethyl(phenyl)-silylmethyl 3-phenoybenzyl ethers, such as
dimethyl-(4-ethoxyphenyl)silylmethyl 3-phenoxybenzyl ether or
(dimethylphenyl)-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)-silanes, such as,
for example,
(4-ethoxyphenyl)-[3-(4-fluoro-3-phenoxy-phenyl-propyl]dimethyl
silane.
[0087] Pyrethroids, such as allethrin, alphamethrin, bioresmethrin,
byfenthrin, cycloprothrin, cyfluthrin, decamethrin, cyhalothrin,
cypermethrin, deltamethrin, alpha-cyano-3-phenyl-2-methylbenzyl
2,2-dimethyl-3-(2-chloro-2-trifluoro-methylvinyl)cyclopropanecarboxylate,
fenpropathrin, fenfluthrin, fenvalerate, flucythrinate, flumethrin,
fluvalinate, permethrin, resmethrin and tralomethrin;
[0088] Nitroimines and nitromethylenes, such as
1-[(6-chloro-3-pyridinyl)-methyl]-4,5-dihydro-N-nitro-1H-imidazol-2-amine-
(imidacloprid).
[0089] The mixtures, concentrates and formulations according to the
invention which have been prepared in this manner are not only
active against the abovementioned fungi but also, if they contain
an insecticide, against insects which destroy materials. The
following insects which destroy materials may be mentioned by way
of example, without imposing any limitation:
[0090] A: Dermaptera: [0091] Sirex juvencus [0092] Urocerus augur
[0093] Urocerus gigas [0094] Urucerus gigas taignus
[0095] B: Coleoptera: [0096] Anobium punctatum [0097] Apate
monachus [0098] Bostrychus capucins [0099] Chlorophores pilosus
[0100] Dendrobium pertinex [0101] Dinoderus minutus [0102] Ernobius
mollis [0103] Heterobostrychus brunneus [0104] Hylotrupes bajulus
[0105] Lyctus africanus [0106] Lyctus brunneus [0107] Lyctus
linearis [0108] Lyctus planicollis [0109] Lyctus pubescens [0110]
Minthea rugicollis [0111] Priobium carpini [0112] Ptilinus
pecticornis [0113] Sinoxylon spec. [0114] Trogoxylon aequale [0115]
Trypto dendron spec. [0116] Xestobium rufovillosum [0117] Xyleborus
spec.
[0118] C: Isoptera: [0119] Coptotermes formosanus [0120]
Cryptotermes brevis [0121] Heterotermes indicola [0122] Kalotermes
flavicollis [0123] Mastotermes darwiniensis [0124] Reticulitermes
flavipes [0125] Reticulitermes lucifugus [0126] Reticulitermes
santonensis [0127] Zootermopsis nevadensis
[0128] Other active compounds which are suitable are algicides,
molluscicides or active compounds against sea animals which
colonise, for example, ship's bottom paints.
[0129] The following are particularly preferred as components in
mixtures:
[0130] dichlofluanid, tolylfluanid,
[0131] benzyldimethyldodecylammonium chloride,
didecyldimethylammonium chloride,
[0132] tebuconazole, propiconazole, azaconazole, hexaconazole,
[0133] 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propinyl
n-butylcarbamate,
[0134] o-phenylphenol, m-phenylphenol, p-phenylphenol,
3-methyl-4-chlorophenol, thiocyanatomethylthiobenzothiazole,
[0135] N-methylisothiazolin-3-one,
5-chloro-N-methylisothiazolin-3-one,
4,5-dichloro-N-octylisothiazolin-3-one,
N-octyl-isothiazolin-3-one,
[0136] benzyl alcohol mono(poly)-hemiformal,
N-methylolchloro-acetamide,
[0137] phoxim,
[0138] cyfluthrin, permethrin, cypermethrin, deltamethrin,
imidacloprid.
[0139] The microbicidal compositions or concentrates used for the
protection of industrial materials contain the active compound of
the formula (I) in a concentration from 0.01 to 95% by weight, in
particular 0.01 to 60% by weight, and additionally, if appropriate,
0.001 to 95% by weight of one or more other suitable fungicides,
insecticides or other active compounds as mentioned above.
[0140] The compositions according to the invention allow in an
advantageous manner the microbicidal compositions available to date
to be replaced by more effective ones. They have good stability
properties and, advantageously, a broad spectrum of action.
EXAMPLE 1
[0141] Inhibition test on giant colonies of Basidiomycetes
[0142] Mycelium sections were removed from colonies of Gloeophyllum
trabeum, Coniophora puteana, Poria placenta, Lentinus tigrinus,
Coriolus versicolor and Stereum sanguinolentum and incubated on an
agar medium containing malt extract peptone at 26.degree. C. The
inhibition of hyphal growth on active-compound-containing media was
compared with the longitudinal growth on media without an addition
of active compound and rated as per cent inhibition.
[0143] At a concentration of 10 ppm, a 100% inhibition is obtained
with the compound cyproconazole.
* * * * *