CA1094258A - Fungicidal agent for the protection of materials - Google Patents
Fungicidal agent for the protection of materialsInfo
- Publication number
- CA1094258A CA1094258A CA272,661A CA272661A CA1094258A CA 1094258 A CA1094258 A CA 1094258A CA 272661 A CA272661 A CA 272661A CA 1094258 A CA1094258 A CA 1094258A
- Authority
- CA
- Canada
- Prior art keywords
- imidazol
- dimethylbutan
- chlorophenoxy
- leather
- fungi
- 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.)
- Expired
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Fungicidal agent for the protection of materials Abstract Materials such as lime wash, paint, paper, wood, plastic, leather, artificial leather, carpeting, canvas, a textile, bitumen, glue, rubber or plaster is protected against fungi by applying thereto, either on the surface or throughout the material, a fungicidally effective amount of 1-(4-chloro-phenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one.
Le A 16 895
Le A 16 895
Description
T.ype IIb The present invention relates to the use of the known compound 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethyl-butan-2-one as a fungicidal agent for the protection of materials, especially in the domestic and industrial fields.
It has already been disclosed that 1-(4-chlorophenoxy)-l-imidazol-1-yl-3,3-dimethylbutan-2-one displays a good spectrum of action against fungi which are pathogenic to man, animals and plants and also has a microbicidal action (see German Offenlegungsschriften (German Published Specifications)
It has already been disclosed that 1-(4-chlorophenoxy)-l-imidazol-1-yl-3,3-dimethylbutan-2-one displays a good spectrum of action against fungi which are pathogenic to man, animals and plants and also has a microbicidal action (see German Offenlegungsschriften (German Published Specifications)
2,105,490 and 2,325,156). Moreover, it i8 already known that 2-[N-(trifluoromethyl)-N-(fluorodichloromethylthio)-amino]-benzoic acid salicyl ester (the active compound in the B commercial product EULAN ASEPT P) is used as a disinfectant in the domestic field (see German Offe~legungs~chrift (German Iublished Specification) 1,919,180~ However, its action is not always quite satisfactory, especially against moulds and blastomyces.
It has been found that 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one of the formula Cl ~ O-CH-CO-C(CH~)~
I~N ( I ) can be employed with good success as a fungicidal agent, which has a preventive and fungus infection-preventing action, for the protection of materials, especially in the domestic and industrial fields.
Accordingly, the present invention prOovides a method ~e A 16 895 - 2 - ~
Tr~cle~ark 105'4258 of combating the growth of fungi in or on an inanimate domestic material subject to fungal attack, which comprises applying to the material 1-(4-chlorophenoxy)-l-imidazol-l-yl-3,3-dimethylbutan-2-one of the formula Cl ~ 0-CH-C0-C(CH3)3 (I) N
~ N
The present invention also provides inanimate domestic mate-rials protected from damage by fungi by the application thereto of 1-(4-chlorophenoxy)-l-imidazol-l-yl-3,3-dimethylbutan-2-one.
Surprisingly, it is precisely against the groups of fungi which are to be combated for the protection of materials that 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one displays a better action than 2-[N-(trifluoromethyl)-N-~fluorodichloromethylthio)-amino]-benzoic acid salicyl ester, which is known from the state of the art, has been used for some time for antimicrobial treatment and is an active compound of the same general type of active compound. Since the compound to be used according to the invention has a particularly broad spectrum of action and a high intensity of action, especially against moulds, and, at the same time, has advantageous physical properties, its successful use for the protection of material is ensured. This represents an enrichment of the art.
The incorporation of the active compound into materials which are exposed to attack by fungi inhibits the growth of the fungi; the materials thus retain their original value. The compound is non-volatile, insoluble in water, insensitive to light and stable to heat, so that it is stable in such materials for long periods. Examples of materials on which the growth of fungi has an adverse effect are lime washes, latex paints, wallpapers, joints in tiled walls, furniture, leather, artificial leathers, bathmats, shower curtains, r ~ ~ 3 ~
10~42~8 textiles, carpeting and tent equipment.
In the ~ield of material protection the fungi which occur are, in particular, of the following classes and species:
(1) Wood: BasidiomYcetes, AscomYcetes and Fun~i ImPerfecti, especially Merulius lacrimans and Coniophora puteana and brown rot fungi, wood rot fungi, blue moulds and moulds. ~hese can lead to the discoloration and weakening of wood materials and even to their destruction.
(2) Cellulose and paper (e.g. ~allpaper~ and books); in particular AsPer~illus species and Penicillium and other moulds as well as further fungi which destroy wood.
It has been found that 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one of the formula Cl ~ O-CH-CO-C(CH~)~
I~N ( I ) can be employed with good success as a fungicidal agent, which has a preventive and fungus infection-preventing action, for the protection of materials, especially in the domestic and industrial fields.
Accordingly, the present invention prOovides a method ~e A 16 895 - 2 - ~
Tr~cle~ark 105'4258 of combating the growth of fungi in or on an inanimate domestic material subject to fungal attack, which comprises applying to the material 1-(4-chlorophenoxy)-l-imidazol-l-yl-3,3-dimethylbutan-2-one of the formula Cl ~ 0-CH-C0-C(CH3)3 (I) N
~ N
The present invention also provides inanimate domestic mate-rials protected from damage by fungi by the application thereto of 1-(4-chlorophenoxy)-l-imidazol-l-yl-3,3-dimethylbutan-2-one.
Surprisingly, it is precisely against the groups of fungi which are to be combated for the protection of materials that 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one displays a better action than 2-[N-(trifluoromethyl)-N-~fluorodichloromethylthio)-amino]-benzoic acid salicyl ester, which is known from the state of the art, has been used for some time for antimicrobial treatment and is an active compound of the same general type of active compound. Since the compound to be used according to the invention has a particularly broad spectrum of action and a high intensity of action, especially against moulds, and, at the same time, has advantageous physical properties, its successful use for the protection of material is ensured. This represents an enrichment of the art.
The incorporation of the active compound into materials which are exposed to attack by fungi inhibits the growth of the fungi; the materials thus retain their original value. The compound is non-volatile, insoluble in water, insensitive to light and stable to heat, so that it is stable in such materials for long periods. Examples of materials on which the growth of fungi has an adverse effect are lime washes, latex paints, wallpapers, joints in tiled walls, furniture, leather, artificial leathers, bathmats, shower curtains, r ~ ~ 3 ~
10~42~8 textiles, carpeting and tent equipment.
In the ~ield of material protection the fungi which occur are, in particular, of the following classes and species:
(1) Wood: BasidiomYcetes, AscomYcetes and Fun~i ImPerfecti, especially Merulius lacrimans and Coniophora puteana and brown rot fungi, wood rot fungi, blue moulds and moulds. ~hese can lead to the discoloration and weakening of wood materials and even to their destruction.
(2) Cellulose and paper (e.g. ~allpaper~ and books); in particular AsPer~illus species and Penicillium and other moulds as well as further fungi which destroy wood.
(3) Textiles and leather: moulds (AsPer~illus, Penicillium, Verticillium and the like) and wood rot iungi. These lead to a reduction in the strength of fibres and leather and to dis-colorations (mould stains on textiles and the red coloration of chrome leather).
(4) Paints, glues and bitumens: moulds and blue moulds, which lead to discolorations due to decomposition of the dye-stuffs or due to the production of dyestuffs by the moulds themselves.
The high intensity of action against Pit,Y~rosporu-m o~ale, which belongs to the Blastomyces~ against moulds, such as AsPer~illus ni~er, Peni¢illium comune and ~rYsiPhe ~raminis, and against ~un~i ImPer~eoti, such ~8 Colletotrioh~um coffeanum, and also the sporicidal action at oonoentrations of 10 mcg/ml against spores of DermatoPhytes and AsPerl2illu~
are to be particularly mentioned. In vitro, the compound displays a high intensity o~ action and has a mainly fungi-statio type of aotion, that i8 to say it inhibits the growth of fungi; iungicidal eiieots (destruction oi fungi) oan be ~e A ~6 895 - 4 -lOg~z~
achieved with 5 to 10 times the minimum inhibitory ,concen-tration (so-called MIC values).
In addition, the compound to be used according to the invention displays a bactericidal action.
The active compound which can be employed according to the invention can be used in an unmodi~ied form or together with a carrier, for example dispersed on a finely divided solid, or as a dust. Such mixtures can also be dispersed in water with the aid of a wetting agent and the resulting emulsions can be used as a spray. With other procedures, the products can be used as active compounds in solvent solutions, oil-in-water emulsions or water-in-oil emulsions. ~he mixtures can be formulated a~ concentrate~ and then diluted with further liquid or ~olid auxiliaries in order to prepare the final mixture to be u~ed for treatment. ~ood results are obtained in particular when mixtures which contain 0.5 to 3% of the active compound are used.
The diverse application possibilities can be seen from the examples which follow:
E2amPle A: MIC values in respect of pathogenic ~ungus species and bacteria important in material protection.
T,Ype of MIC Values or~anism sPecies in mc~/ml DermatoPhYtes ~ichoPhYton menta~ro~Ytes rubrum verruscosum EPidermop~yton ~loccosum MicrosPoron canis ~elineum Blsstomvces Candida albicans troPicalis ~e A 16 895 _ 5 _ - 1~9~Z58 Type of MIC values or~anism sPecies in mCR~
Pseudotropicalis krusei 1-4 ToruloPsis ~labrata 4 CrYPtococcus neoformans 1-4 Pit.Yrosporum ovale 0.25-0.5 Biphase fungi Histoplasma caPsulatum Coccidiodes immitis Sporothri~ Schenckii 2 Moulds AsPer~illus fumi~atu~ 2 ni~er Penicillium comune Madurella ~risea Fun~i ImPerfecti cercosPora musae 5 Colletotrichum coff. 5-10 Basidiomycetes HYPnochus sasakii 10 (MIC 50) .
Bacteria StaPh~lococcus aureus 50 StrePtococci 1 oo ~e A 16 895 - 6 -Z~8 ~H
o O ¦ O
asuaunlab~eo o I ô
uaa 0 oO I oO
C~OIIBA O
OsaoA~Oll~eBa o I o sa~ o ~s~ua~ o I o UO~ tl ol~Fl~ 0 la~Fu o o snll~lacL
oo o sna~IIa~ 0 '~snllF~Ia~s~ ~r V
~,8UB~Fq~B O 8 Bpl:pUBD O ¦ O
~a~s o ~ o ,~ Sa;~ OlB~ Bs 0 1 ~D
nems ~
~n~o~Ol~Bl S o I o sno~la4uasa~ ~ ~ o ,<~ H
3 ~
~e A 16 895 - 7 -~0~21,8 ~xamPle ~: Finishing of ~hoe intersole material Test arran~ements:
(1) Direct contamination test A piece, 3 x 3 cm in size, of the plastic intersole material which contained 1.5 per cent by weight of the active compound was placed, alongside a blank control, in humid ~_~ chambers, saturated with Nervina*malt solution and inoculated with about 2-3 x 103 germinative particles or cells of ~richo~hYton menta~rophytes and ~richophYton rubrum as proto-types of DermatophYtes, Candida albicans as a typical yeast and As~er~illus fumi~atus and Penicillum comune as re-presentatives of the group of moulds.
The material prepared in this way was incubated for 7 days at 28C and from the 3rd day the germ growth was checked daily.
(2) A~ar Diffusion test Pieces of the intersole material approximately 1 x l cm in size were laid in Petri dishes and covered with a layer of Sabouraud agar. After the agar had solidified, 1 x 105 infectious particles of the fungus species ~ri¢hoPhYton menta~roPhYtes, ?richoPhYton rubrum, Candida albicans. AsPer ~illus fumi~atus and Penicillium comune, suspended in 0.5 ml of physiological sodium chloride solution, were spread homogeneously in the Petri dishes using a spatula and the Petri disheæ were incubated for 4 days at 28C.
Results:
(1) Direct contamination test On the control material which had not been finished all the germs displayed normal growth. Compared with the ~o control, the material finished with 1-(4-chlorophenoxy)-1-~e A 16 895 - 8 -l~9~Z5~
imidazol-1-yl-3,3-dimethylbutan-2-one displayed an approxi-mately 80~o inhibition of the growth of the germs in the case o~ Dermatophvtes and AsPer~ us~ as well as Penicillium, and an approximately 30~o inhibition of the growth in the case of Candida.
-When the test was repeated using plastic material which contained 2 to 3 per cent by weight of the active compound this led to complete inhibition o~ the erowth with all the fungi te~ted.
(2) A~ar diffusion te~t ~he inhibition zones obtained in the dif~usion tect are compiled in the table which follows:
Formulation Inhibition zones in mm (diameter) for Cand. Trich. Trich. ABP.
alb. ment. rubr. fum.
Control O O O O
l .5% of active compound 38 38 38 35 2% of active compound 38 46 45 38 3% of active compound 41 50 50 39 ExamPle D: Finishing of leather fibre material ~he material was tested by the contamination test and the agar diffusion test in accordance with the test arranee-ments in Example C.
Composition of the material: 70 parts of leather fibre, 30 parts of natural rubber, corresponding to 50 parts oi 60%
Bl 25 strength natural latex, 1.5 parts of Vulkanox NKF (an adhesive) and (a) 2 parts of the active compound or (b) 3 parts of the active compound.
~e A 16 895 _ 9 _ The tests were carried out on the DermatoPh~tes ~pecies ~richoph~ton menta~roph,yte~ and ~richoph,yton rubrum, on the mould Asper~illus fumi~atus and the yeast Candida albicans.
Result:
Both compositions were completel,y effective in the contamination test and in the agar diffusion test.
~e A 16 ~95 - 10 -lO9~Z~
~ DD = : _ D~l o~~
~I~o~
~b-,~1 bl~ ~
o oO o oO
o~ ~ o tq ~ ~ ~ ~ . ~
æ H H
~e A 16 895 109~2S8 (2) Spray formulation III (according to Example F) was tested against the following germ carriers:
shoe leather test germs:
textile mixed fabric AsPer~ us terreus raised fibre wall covering and filter paper Trichoderma viride 2,000 mould colonies per germ carrier were used as the seed germs.
Result:
With the spraying times o~ 1 and 2 seconds, the above-mentioned germ carriers still displayed no growth after 14 days.
E~ample F: Formulations for aerosol cans Formulation I
0.5% of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethyl-butan-2-one, 0.1% of Evergreen~10 745 HIR (per~ume oil as the aro~a component), 39.4% of isopropanol and 60~0~o Of Frigen 11/12 (30:70) (Frigen~11 is CCl3F; Frigen~ 2 is CCl2F2).
Formulation II
0.5% of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethyl-butan-2-one, 0.1% o~ Evergreen~10 745 H+R, 39.4% of ethanol and 60.0% of Frigen~11/12 (30:70).
Formulation III
0.5% of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one, 0.1% of Evergreen~10 745 H+R, 59.5% of isopropanol and 39.9~o of Frigen 11/12 (30:70).
Preparative E~amPle Cl ~ -CH-C0-C(CH3)3 (I) L~
~e A 16 895 - ~2 -10942~8 After being dissolved in 120 ml of acetonitrile, 12.25 g (0.05 mole) of 1-bromo-1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one and 12 g (0.18 mole) of imidazole were heated to the boil under reflux for 18 hours. After the solvent had been distilled off in vacuo, 150 ml of water were added to the residue and the aqueous phase was then treated three times more with 30 ml of water in each case and dried and the solvent was distilled off _ vacuo. After recrystallising the residue from about 400 ml of ligroin, 10.5 g (72% o~ theory) of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one with a melting point of 135C were obtained.
l-~romo-1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one, which was used as the starting material, was obtained from 4-chlorophenol and bromopinacoline with subsequent bromination with bromine at 140C (melting point 80C).
~e A 16 895 - 13 -
The high intensity of action against Pit,Y~rosporu-m o~ale, which belongs to the Blastomyces~ against moulds, such as AsPer~illus ni~er, Peni¢illium comune and ~rYsiPhe ~raminis, and against ~un~i ImPer~eoti, such ~8 Colletotrioh~um coffeanum, and also the sporicidal action at oonoentrations of 10 mcg/ml against spores of DermatoPhytes and AsPerl2illu~
are to be particularly mentioned. In vitro, the compound displays a high intensity o~ action and has a mainly fungi-statio type of aotion, that i8 to say it inhibits the growth of fungi; iungicidal eiieots (destruction oi fungi) oan be ~e A ~6 895 - 4 -lOg~z~
achieved with 5 to 10 times the minimum inhibitory ,concen-tration (so-called MIC values).
In addition, the compound to be used according to the invention displays a bactericidal action.
The active compound which can be employed according to the invention can be used in an unmodi~ied form or together with a carrier, for example dispersed on a finely divided solid, or as a dust. Such mixtures can also be dispersed in water with the aid of a wetting agent and the resulting emulsions can be used as a spray. With other procedures, the products can be used as active compounds in solvent solutions, oil-in-water emulsions or water-in-oil emulsions. ~he mixtures can be formulated a~ concentrate~ and then diluted with further liquid or ~olid auxiliaries in order to prepare the final mixture to be u~ed for treatment. ~ood results are obtained in particular when mixtures which contain 0.5 to 3% of the active compound are used.
The diverse application possibilities can be seen from the examples which follow:
E2amPle A: MIC values in respect of pathogenic ~ungus species and bacteria important in material protection.
T,Ype of MIC Values or~anism sPecies in mc~/ml DermatoPhYtes ~ichoPhYton menta~ro~Ytes rubrum verruscosum EPidermop~yton ~loccosum MicrosPoron canis ~elineum Blsstomvces Candida albicans troPicalis ~e A 16 895 _ 5 _ - 1~9~Z58 Type of MIC values or~anism sPecies in mCR~
Pseudotropicalis krusei 1-4 ToruloPsis ~labrata 4 CrYPtococcus neoformans 1-4 Pit.Yrosporum ovale 0.25-0.5 Biphase fungi Histoplasma caPsulatum Coccidiodes immitis Sporothri~ Schenckii 2 Moulds AsPer~illus fumi~atu~ 2 ni~er Penicillium comune Madurella ~risea Fun~i ImPerfecti cercosPora musae 5 Colletotrichum coff. 5-10 Basidiomycetes HYPnochus sasakii 10 (MIC 50) .
Bacteria StaPh~lococcus aureus 50 StrePtococci 1 oo ~e A 16 895 - 6 -Z~8 ~H
o O ¦ O
asuaunlab~eo o I ô
uaa 0 oO I oO
C~OIIBA O
OsaoA~Oll~eBa o I o sa~ o ~s~ua~ o I o UO~ tl ol~Fl~ 0 la~Fu o o snll~lacL
oo o sna~IIa~ 0 '~snllF~Ia~s~ ~r V
~,8UB~Fq~B O 8 Bpl:pUBD O ¦ O
~a~s o ~ o ,~ Sa;~ OlB~ Bs 0 1 ~D
nems ~
~n~o~Ol~Bl S o I o sno~la4uasa~ ~ ~ o ,<~ H
3 ~
~e A 16 895 - 7 -~0~21,8 ~xamPle ~: Finishing of ~hoe intersole material Test arran~ements:
(1) Direct contamination test A piece, 3 x 3 cm in size, of the plastic intersole material which contained 1.5 per cent by weight of the active compound was placed, alongside a blank control, in humid ~_~ chambers, saturated with Nervina*malt solution and inoculated with about 2-3 x 103 germinative particles or cells of ~richo~hYton menta~rophytes and ~richophYton rubrum as proto-types of DermatophYtes, Candida albicans as a typical yeast and As~er~illus fumi~atus and Penicillum comune as re-presentatives of the group of moulds.
The material prepared in this way was incubated for 7 days at 28C and from the 3rd day the germ growth was checked daily.
(2) A~ar Diffusion test Pieces of the intersole material approximately 1 x l cm in size were laid in Petri dishes and covered with a layer of Sabouraud agar. After the agar had solidified, 1 x 105 infectious particles of the fungus species ~ri¢hoPhYton menta~roPhYtes, ?richoPhYton rubrum, Candida albicans. AsPer ~illus fumi~atus and Penicillium comune, suspended in 0.5 ml of physiological sodium chloride solution, were spread homogeneously in the Petri dishes using a spatula and the Petri disheæ were incubated for 4 days at 28C.
Results:
(1) Direct contamination test On the control material which had not been finished all the germs displayed normal growth. Compared with the ~o control, the material finished with 1-(4-chlorophenoxy)-1-~e A 16 895 - 8 -l~9~Z5~
imidazol-1-yl-3,3-dimethylbutan-2-one displayed an approxi-mately 80~o inhibition of the growth of the germs in the case o~ Dermatophvtes and AsPer~ us~ as well as Penicillium, and an approximately 30~o inhibition of the growth in the case of Candida.
-When the test was repeated using plastic material which contained 2 to 3 per cent by weight of the active compound this led to complete inhibition o~ the erowth with all the fungi te~ted.
(2) A~ar diffusion te~t ~he inhibition zones obtained in the dif~usion tect are compiled in the table which follows:
Formulation Inhibition zones in mm (diameter) for Cand. Trich. Trich. ABP.
alb. ment. rubr. fum.
Control O O O O
l .5% of active compound 38 38 38 35 2% of active compound 38 46 45 38 3% of active compound 41 50 50 39 ExamPle D: Finishing of leather fibre material ~he material was tested by the contamination test and the agar diffusion test in accordance with the test arranee-ments in Example C.
Composition of the material: 70 parts of leather fibre, 30 parts of natural rubber, corresponding to 50 parts oi 60%
Bl 25 strength natural latex, 1.5 parts of Vulkanox NKF (an adhesive) and (a) 2 parts of the active compound or (b) 3 parts of the active compound.
~e A 16 895 _ 9 _ The tests were carried out on the DermatoPh~tes ~pecies ~richoph~ton menta~roph,yte~ and ~richoph,yton rubrum, on the mould Asper~illus fumi~atus and the yeast Candida albicans.
Result:
Both compositions were completel,y effective in the contamination test and in the agar diffusion test.
~e A 16 ~95 - 10 -lO9~Z~
~ DD = : _ D~l o~~
~I~o~
~b-,~1 bl~ ~
o oO o oO
o~ ~ o tq ~ ~ ~ ~ . ~
æ H H
~e A 16 895 109~2S8 (2) Spray formulation III (according to Example F) was tested against the following germ carriers:
shoe leather test germs:
textile mixed fabric AsPer~ us terreus raised fibre wall covering and filter paper Trichoderma viride 2,000 mould colonies per germ carrier were used as the seed germs.
Result:
With the spraying times o~ 1 and 2 seconds, the above-mentioned germ carriers still displayed no growth after 14 days.
E~ample F: Formulations for aerosol cans Formulation I
0.5% of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethyl-butan-2-one, 0.1% of Evergreen~10 745 HIR (per~ume oil as the aro~a component), 39.4% of isopropanol and 60~0~o Of Frigen 11/12 (30:70) (Frigen~11 is CCl3F; Frigen~ 2 is CCl2F2).
Formulation II
0.5% of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethyl-butan-2-one, 0.1% o~ Evergreen~10 745 H+R, 39.4% of ethanol and 60.0% of Frigen~11/12 (30:70).
Formulation III
0.5% of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one, 0.1% of Evergreen~10 745 H+R, 59.5% of isopropanol and 39.9~o of Frigen 11/12 (30:70).
Preparative E~amPle Cl ~ -CH-C0-C(CH3)3 (I) L~
~e A 16 895 - ~2 -10942~8 After being dissolved in 120 ml of acetonitrile, 12.25 g (0.05 mole) of 1-bromo-1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one and 12 g (0.18 mole) of imidazole were heated to the boil under reflux for 18 hours. After the solvent had been distilled off in vacuo, 150 ml of water were added to the residue and the aqueous phase was then treated three times more with 30 ml of water in each case and dried and the solvent was distilled off _ vacuo. After recrystallising the residue from about 400 ml of ligroin, 10.5 g (72% o~ theory) of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one with a melting point of 135C were obtained.
l-~romo-1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one, which was used as the starting material, was obtained from 4-chlorophenol and bromopinacoline with subsequent bromination with bromine at 140C (melting point 80C).
~e A 16 895 - 13 -
Claims (8)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method of combating the growth of fungi in or on an inanimate domestic material subject to fungal attack, which comprises applying to the material 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one, of the formula (I)
2. A method according to claim 1 wherein the 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one is applied in admixture with a diluent or carrier.
3. A method according to claim 2, in which a composition is applied containing 0.5 to 3% by weight of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one.
4. A method according to claim 1, in which the 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one is incorporated into the said mate-rial.
5. A method according to claim 1, 3 or 4, in which the said material is a lime wash, a paint, paper, wood, a plastics material, leather, arti-ficial leather, carpeting, canvas, a textile material, bitumen, a glue, rubber or plaster.
6. An inanimate domestic material normally subject to fungal attack which has been protected from damage by fungi by the application thereto of 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one.
7. A material according to claim 6, wherein the 1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one is incorporated in said material.
8. A material according to claim 6 or 7 wherein said material is a lime wash, a paint, paper, wood, a plastics material, leather, artificial leather, carpeting, canvas, a textile material, bitumen, a glue, rubber or plaster.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA272,661A CA1094258A (en) | 1977-02-25 | 1977-02-25 | Fungicidal agent for the protection of materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA272,661A CA1094258A (en) | 1977-02-25 | 1977-02-25 | Fungicidal agent for the protection of materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094258A true CA1094258A (en) | 1981-01-27 |
Family
ID=4108018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA272,661A Expired CA1094258A (en) | 1977-02-25 | 1977-02-25 | Fungicidal agent for the protection of materials |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1094258A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4670336A (en) * | 1984-08-11 | 1987-06-02 | Bayer Aktiengesellschaft | Laundry-stable, antimicrobially-active fibers and filaments and the production thereof |
-
1977
- 1977-02-25 CA CA272,661A patent/CA1094258A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4670336A (en) * | 1984-08-11 | 1987-06-02 | Bayer Aktiengesellschaft | Laundry-stable, antimicrobially-active fibers and filaments and the production thereof |
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