CA1159604A - Aqueous slurry or pasty fungicidal composition - Google Patents
Aqueous slurry or pasty fungicidal compositionInfo
- Publication number
- CA1159604A CA1159604A CA000364517A CA364517A CA1159604A CA 1159604 A CA1159604 A CA 1159604A CA 000364517 A CA000364517 A CA 000364517A CA 364517 A CA364517 A CA 364517A CA 1159604 A CA1159604 A CA 1159604A
- Authority
- CA
- Canada
- Prior art keywords
- maleimide
- ppm
- present
- fungi
- aqueous
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues thereof
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
- D21C9/008—Prevention of corrosion or formation of deposits on pulp-treating equipment
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Organic Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
An aqueous slurry or pasty fungicidal composition such as an aqueous emulsion paint, a water paint, an aqueous adhesive, a printing paste and a pulp slurry contains N-(2,4,6-trichlorophenyl) maleimide as an active ingredient.
An aqueous slurry or pasty fungicidal composition such as an aqueous emulsion paint, a water paint, an aqueous adhesive, a printing paste and a pulp slurry contains N-(2,4,6-trichlorophenyl) maleimide as an active ingredient.
Description
l 15~6~
The present invention relates to industrial aqueous fungicidal compositions which protect industrial products and raw materials from microorganisms, especially fungi.
Heretofore, the economic growth caused by the growth of microorganisms, such as bac-teria and :Eungi, in industrial produc-ts and raw materials has been serious. For example, fun~i, such as Asperigllus and Cladosporium grow on walls and ceilings, coated with an aqueous emulsion paint or a water paint causing serious disadvantages in hygiene and appearance. Fungi such as Chaetomium, Rhizopus and Aspergillus grow on products such as soap cartons, causing serious damage including deterioration of paper strength and hygiene. Various chemicals have been proposed to prevent such damage. However they are not satisfactory.
In attemp-ts to find chemicals effective for protecting such industrial products and raw materials against such serious damage caused by microor~anisms N-arylmaleimides known as agricultural germicides have been studied. As a result, N-(3,5-dichlorophenyl)maleimide known to have germicidal activity aga~nst bacteria such as Staphylococcus aurcus and Eschericha coli (Japanese Examined Patent Publication No.
38819/1974), has been found to have inferior fungicidal activity to find fungicidal compounds for industrial purposes.
The present invention provides an industrial aqueous fun~icidal composition, especially an aqueous slurry or pasty fungicidal composition, such as an aqueous emulsion paint, a water paint, an aqueous adhesive, a printing paste and a pulp slurry.
According to the present invention -there i5 provided an aqueous slurry or pasty fungicidal composition including N-(2,4,6-trichlorophenyl)maleimide as an active ingredient.
It has been found that N-(2,4,6-trichlorophenyl) ; .
l 15980~
maleimide having a meltiny point of 130DC as colorless powdery ~ crystals obtained by a dehydrocyclization of 2,4,6-trichloro-i aniline and maleic anhydride has an especially good fungicidal activity agatnst noxious funyi and is very effective for prol-ecting various industrial products and raw materials from damage due to microorganisms, especially fungi. The present invention provides industrial fungicidal compositions containing N-(2,4,6-trichlorophenyl)maleimide as an active ingredient. -N-(2,4,6-trichlorophenyl)maleimide used in the present i invention can be produced by adding a solution of 2,4,6-trichloro-~ aniline in a solvent, such as toluene dropwise into a solution , :
of maleic anhydride in a solvent, such as toluene, with stirring at about 65C for 2 hours and adding sulfuric acid and refluxing the mixture with stirring for 4 hours to effect reaction and distilling off the solvent after the reaction, pouring the reaction mixture into water and then filtering the precipitated crystals having a melting point of 130 to 132C.
The compound of the present invention can be used by itself and also can be used in a suitable form such as wettable powder, dust, tablet or suspension obtained by admixing with a diluent, or bulking filler or an additive, such as a dispersing ; agent, penetrant and a wetting agent. Most conventional industrial fungicides are not easily soluble in organic solvents whereby their field of the application is quite limited.
However, the compound of the present invention is readily soluble in most solvents, such as benzene, toluene, xylene, solvent naphtha, chloroform, methyl isobutyl ketone, and dimethylformamide whereby an emulsion type composition can be prepared and the field of application are not so limited. The compound of the present invention can be combined with conventional industrial - funyicide such as phenol type fungicides e.g. 2,4,6-trichloro-~ ..
l 1~9604 phenol; chlorine type fungicides e.y. tetrachloroi oph-thalnitrile, and organ~tin compound fungicides e.g. tributyl-tin-oxide and such a synergistic effect may be achieved without reducing the effect of the compounds.
The N-arylmaleimides are known agricultural germicides.
The agrlcultural germicides controlling plant virus growing on plants are quite different from the industrial fungicides for inhibiting fungi grown on industrial products and raw materials in view of locations of applications, types of microorganisms to be controlled and physical properties of the compositions.
Although N-(3,5-dichlorophenyl)maleimide has high activity against viruses, the N-(2,4,6-trichlorophenyl)maleimide of the present invention has greatly superior activity against fungi. An excellent fungicidal effect when used as an industrial fungicide is found. N-(2,4,6-trichlorophenyl)maleimide is especially superior to other maleimide derivatives in the form of an aqueous suspension or pasty composition, such as an aqueous emulsion paint, a water paint, an aqueous adhesive, especially adhesives for bonding paper, etc., a printing paste and a pulp slurry. N-(2,4,6-trichlorophenyl)maleimide is preferably incorporated in the composition in the form solubilized with a surfactant, especially in the form of an emulsifiable concentrate or a wettable powder.
The content of N-(2,4,6-trichlorophenyl)maleimide in the composition is not critical and is sufficient to impart the fungicidal activity and can be considered from the minimal growth inhibition, and is preferably more than 100 ppm, especially more than 200 pp~.
The present invention will be further illustrated by the following Examples and References:
_ AMPLE 1 (Tests for minimal growth inhibition concentration) ~ 159604 Each wettable powder was prepared by mixing and pulver-izing 50 wt. parts of each active ingredient, 2 wt. parts of a surfactant (Neopelex: a trademark of Kao-Atlas Co.), 2 wt.
parts of an extract (Sunex P: a trademark of Sanyo Pulp Co.), and 46 wt. parts of diatomaceous earth. Each minimal growth inhibition concentration against various fungi was measured by the agar dilution method by using the prepared wettable powders. The results are shown in Table 1.
~ . .
¦Mlnimal growth inhibition concentration (ppm) Active ingredient I_ _ A.n P.c T.v R.n C.h C.g , _ _. _ N--(2,4,6-trichloro-phenyl)maleimide 25 12.5 25 100 50 100 References:
(a) 2-(4-thiazoyl) benzimidazole 50 50 100 500 100 200 (b) tributyl-tin-oxide 25 12.5 50 250 100 100 (c) N-(3,5-dichloro-phenyl)maleimide 100 100 500 500 250 250 A.n: Aspergillus niger P.c: Penicillium citrinum T.v: Trichoderma viride R.n: Rhizopus nigricans C.h: Cladosporium herbarum C.g: Chaetomium globosum (a) and (b):Commercially available fungicides (c): compound disclosed in Japanese Examined Patent Publication 38819/1974 (Fungicidal Test of Water Paint) -~ 1~9~0d~
A water paint was prepared by mixing 27 wt.o of acrylic emulsion having 50% of a resin content, 8 wt.% of titanium oxide, 23 wt.% of kaoline, 18 wt.% of heavy calcium carbonate, 20 wt.%
of 2% a~ueous solution of carboxymethyl cellulose and 4 wt.% of water Each wet-table powder prepared in Example 1 was incorporated in the water pain-t at a concentration of 2000 ppm or 500 ppm of the active ingredient. The water paints incorporating the wettable powder were tested by the wet fungi resistant test method of Japanese Industrial Standard Z-2911. The results are shown in Table 2.
__ _ _ _ Concent- Culturing time ration Active ingredient(ppm) 3 day 7 day ¦ 14 day N-(2,4,6-trichloro-phenyl) 2000 3 3 3 maleimide 500 3 3 2 . _
The present invention relates to industrial aqueous fungicidal compositions which protect industrial products and raw materials from microorganisms, especially fungi.
Heretofore, the economic growth caused by the growth of microorganisms, such as bac-teria and :Eungi, in industrial produc-ts and raw materials has been serious. For example, fun~i, such as Asperigllus and Cladosporium grow on walls and ceilings, coated with an aqueous emulsion paint or a water paint causing serious disadvantages in hygiene and appearance. Fungi such as Chaetomium, Rhizopus and Aspergillus grow on products such as soap cartons, causing serious damage including deterioration of paper strength and hygiene. Various chemicals have been proposed to prevent such damage. However they are not satisfactory.
In attemp-ts to find chemicals effective for protecting such industrial products and raw materials against such serious damage caused by microor~anisms N-arylmaleimides known as agricultural germicides have been studied. As a result, N-(3,5-dichlorophenyl)maleimide known to have germicidal activity aga~nst bacteria such as Staphylococcus aurcus and Eschericha coli (Japanese Examined Patent Publication No.
38819/1974), has been found to have inferior fungicidal activity to find fungicidal compounds for industrial purposes.
The present invention provides an industrial aqueous fun~icidal composition, especially an aqueous slurry or pasty fungicidal composition, such as an aqueous emulsion paint, a water paint, an aqueous adhesive, a printing paste and a pulp slurry.
According to the present invention -there i5 provided an aqueous slurry or pasty fungicidal composition including N-(2,4,6-trichlorophenyl)maleimide as an active ingredient.
It has been found that N-(2,4,6-trichlorophenyl) ; .
l 15980~
maleimide having a meltiny point of 130DC as colorless powdery ~ crystals obtained by a dehydrocyclization of 2,4,6-trichloro-i aniline and maleic anhydride has an especially good fungicidal activity agatnst noxious funyi and is very effective for prol-ecting various industrial products and raw materials from damage due to microorganisms, especially fungi. The present invention provides industrial fungicidal compositions containing N-(2,4,6-trichlorophenyl)maleimide as an active ingredient. -N-(2,4,6-trichlorophenyl)maleimide used in the present i invention can be produced by adding a solution of 2,4,6-trichloro-~ aniline in a solvent, such as toluene dropwise into a solution , :
of maleic anhydride in a solvent, such as toluene, with stirring at about 65C for 2 hours and adding sulfuric acid and refluxing the mixture with stirring for 4 hours to effect reaction and distilling off the solvent after the reaction, pouring the reaction mixture into water and then filtering the precipitated crystals having a melting point of 130 to 132C.
The compound of the present invention can be used by itself and also can be used in a suitable form such as wettable powder, dust, tablet or suspension obtained by admixing with a diluent, or bulking filler or an additive, such as a dispersing ; agent, penetrant and a wetting agent. Most conventional industrial fungicides are not easily soluble in organic solvents whereby their field of the application is quite limited.
However, the compound of the present invention is readily soluble in most solvents, such as benzene, toluene, xylene, solvent naphtha, chloroform, methyl isobutyl ketone, and dimethylformamide whereby an emulsion type composition can be prepared and the field of application are not so limited. The compound of the present invention can be combined with conventional industrial - funyicide such as phenol type fungicides e.g. 2,4,6-trichloro-~ ..
l 1~9604 phenol; chlorine type fungicides e.y. tetrachloroi oph-thalnitrile, and organ~tin compound fungicides e.g. tributyl-tin-oxide and such a synergistic effect may be achieved without reducing the effect of the compounds.
The N-arylmaleimides are known agricultural germicides.
The agrlcultural germicides controlling plant virus growing on plants are quite different from the industrial fungicides for inhibiting fungi grown on industrial products and raw materials in view of locations of applications, types of microorganisms to be controlled and physical properties of the compositions.
Although N-(3,5-dichlorophenyl)maleimide has high activity against viruses, the N-(2,4,6-trichlorophenyl)maleimide of the present invention has greatly superior activity against fungi. An excellent fungicidal effect when used as an industrial fungicide is found. N-(2,4,6-trichlorophenyl)maleimide is especially superior to other maleimide derivatives in the form of an aqueous suspension or pasty composition, such as an aqueous emulsion paint, a water paint, an aqueous adhesive, especially adhesives for bonding paper, etc., a printing paste and a pulp slurry. N-(2,4,6-trichlorophenyl)maleimide is preferably incorporated in the composition in the form solubilized with a surfactant, especially in the form of an emulsifiable concentrate or a wettable powder.
The content of N-(2,4,6-trichlorophenyl)maleimide in the composition is not critical and is sufficient to impart the fungicidal activity and can be considered from the minimal growth inhibition, and is preferably more than 100 ppm, especially more than 200 pp~.
The present invention will be further illustrated by the following Examples and References:
_ AMPLE 1 (Tests for minimal growth inhibition concentration) ~ 159604 Each wettable powder was prepared by mixing and pulver-izing 50 wt. parts of each active ingredient, 2 wt. parts of a surfactant (Neopelex: a trademark of Kao-Atlas Co.), 2 wt.
parts of an extract (Sunex P: a trademark of Sanyo Pulp Co.), and 46 wt. parts of diatomaceous earth. Each minimal growth inhibition concentration against various fungi was measured by the agar dilution method by using the prepared wettable powders. The results are shown in Table 1.
~ . .
¦Mlnimal growth inhibition concentration (ppm) Active ingredient I_ _ A.n P.c T.v R.n C.h C.g , _ _. _ N--(2,4,6-trichloro-phenyl)maleimide 25 12.5 25 100 50 100 References:
(a) 2-(4-thiazoyl) benzimidazole 50 50 100 500 100 200 (b) tributyl-tin-oxide 25 12.5 50 250 100 100 (c) N-(3,5-dichloro-phenyl)maleimide 100 100 500 500 250 250 A.n: Aspergillus niger P.c: Penicillium citrinum T.v: Trichoderma viride R.n: Rhizopus nigricans C.h: Cladosporium herbarum C.g: Chaetomium globosum (a) and (b):Commercially available fungicides (c): compound disclosed in Japanese Examined Patent Publication 38819/1974 (Fungicidal Test of Water Paint) -~ 1~9~0d~
A water paint was prepared by mixing 27 wt.o of acrylic emulsion having 50% of a resin content, 8 wt.% of titanium oxide, 23 wt.% of kaoline, 18 wt.% of heavy calcium carbonate, 20 wt.%
of 2% a~ueous solution of carboxymethyl cellulose and 4 wt.% of water Each wet-table powder prepared in Example 1 was incorporated in the water pain-t at a concentration of 2000 ppm or 500 ppm of the active ingredient. The water paints incorporating the wettable powder were tested by the wet fungi resistant test method of Japanese Industrial Standard Z-2911. The results are shown in Table 2.
__ _ _ _ Concent- Culturing time ration Active ingredient(ppm) 3 day 7 day ¦ 14 day N-(2,4,6-trichloro-phenyl) 2000 3 3 3 maleimide 500 3 3 2 . _
2~(4-thiazoyl)- 2000 3 3 ¦ 3 benzimldazol 500 3 1 tributyl-tin-oxide 3 N-(3,5-dichloro-phenyl) 2000 3 2 1 maleimide 500 3 0 0 . _ Non-treatment ~ __~
Rating: 3: no growth of fungi 2: growth of fungi in area of less than 1/3 on test piece , ~
~--l 15960~
1: growth of fungi in area of about 1/3 on test piece 0: growth of fungi in area of more than 1/3 on test piece EXA~PLE 3 -(Fungicidal test of printing paste) .
In a 500 ml beaker was placed 300 g of a printing paste as a solution of 1 wt.% wheat starch and 1 wt.~ of tragacanth gum. Each wettable powder prepared in Example 1 was incorporated in the prin-ting paste at a concentration of 1000 ppm or 2000 ppm of the active ingredient. The beaker was sealed with aluminum foil and kept in a constant temperature oven at 30DC. The growth of fungi on the surfaces of the printing pastes were observed. The results are shown in Table 3.
. . _ Concent~ Culturing time ration _ I ~ -Active ingredient (ppm) 4 day 7 day 10 day N-(2,4,6-trichloro- _ phenyl) 2000 _ _ maleimide 1000 _ _ _ -_ 2-(4-thiazoyl)-benzimidazol 2000 _ 1000 ~ ++ '":
tribu~yl-tin-oxide ~ _ . ~
Non-treatment ~ ++ ++
_ting:
-: no growth of fungi +: growth of fungi in area of less than 1/3 on surface in beaker ~,f~ 6 1 ~5960~
+ : growth of fungi in area of about 1/3 on surface in beaker -~: growth of fungi in area of more than 1/3 on surface in beaker.
(Fungicidal test of wall paper) Casein glue as an adhesive was prepared by boiling an aqueous solution of casein.
Each wettable concentrate of Example 1 was incorporated into the adhesive at a concentration of 2000 ppm of the active ingredient. The treated casein glue was used for bonding wall paper on a concrete having a thickness of 5 cm x 5 cm to ob-tain a test piece. The test piece was placed at a center of the plate culture medium made of 1000 ml of water, 40 g of glucose, 10 g of peptone and 25 g of arger in a Petri dish and a suspension of mixed spores of Aspergillus niger, Trichoderma viride, Pencillium citrinum and Rhizopus nigricans was uniformly sprayed in the Petri dish. The Petri dish was covered with a cover and kept in a constant temperature oven at 2~C for 15 days to culture it for 15 days. The results are shown in Table 4.
_ Culturing time Acti~e lngredient ~ day ¦ 10 day ~ 15 day N-(2,4,~-trichloro- _ _ _ phenyl) maleimide .
2-(4-thiazoyl)-ben- _ _ _ zimidazol _ _ tributyl-t~in-oxide _ +
Non-treatment L +-~+
~ `:
l 1~9~04 Rating:
- : no growth of fungi + : growth of fungi in area of less than 1/3 on surface in beaker + : growth of fungi in area of about 1/3 on surface in beaker ~-+: growth of fungi in area of more than 1/3 on surface in beaker Test 1. Funglcidal test of we-t pulp Each emulsifiable concentrate was prepared by mixing 20 wt. parts of each active ingredient, 10 wt. parts of a surfactant (~orpol 800 A: a trademark of Toho Kagaku K.~.), 5 wt. parts of a surfactant (Emulgen 800: a trademark of Kao-Atlas Co.), and 65 wt. parts of xylene. The emulsifiable concentrate was diluted with wa-ter to prepare each emulsion at a concentration of 200 ppm or 50 ppm of the active ingredient.
The emulsion was sprayed by a sprayer at a rate of 30 ml. per 1 kg of a we-t straw pulp! The treated pulp was held in a plastic film bag and kept in a constant temperature oven at 30C to observe the growth of fungi on the surface of wet pulp. The results are shown in Table 5.
The commercially available 2-(4-thiazoyl)benzimidazole was difficulty soluble to organic solvents whereby it could ;-not be emulsified to use it in the test.
TAsLE 5 Concent- Culturing time ration Active ingredient (ppm) 5 day 10 day 20 day _ : .
N-(2,4,6-trichloro- 1 200 _ _ _ phenyl) maleimide ¦ 50 _ _ tributyl-tin-oxide 200 _ _ +++
~ _ _ non-treatment _ ~ _ ++ +~+
:: ' l 15~60~
Test 2. Funyicidal test of wood:
Each emulsifiable concentrate of Test 1 was diluted with water to prepare each emulsion at a concentration of 200 ppm or 50 ppm of the active ingredient. Each pine wood chip (size of 5 cm x 5 cm x 30 cm) having a water content of 70 to 75% was dipped in the emulsion for 3 minutes. The treated pine wood was maintained in a chamber at 30C and a humidity of 80%.
The growth oE fungi on the wood chip was observed. The results are shown in Table 6.
The commercially available 2-(4-thiazoyl) benzimidazole was difficultly soluble in organic so]vents and it could not be emulsified for use in the Test.
_ _ _ _ Concent- Culturing time Active ingredient r(ppm)n 10 day .D d~ 30 day 1~-(2,4,6-trichloro- 200 _ _ _ phenyl)maleimide 50 _ _ _ __ ....
20 ~ L-t.in-oxi ~ ~ _ non-treatment L + ++ +++
::
9_
Rating: 3: no growth of fungi 2: growth of fungi in area of less than 1/3 on test piece , ~
~--l 15960~
1: growth of fungi in area of about 1/3 on test piece 0: growth of fungi in area of more than 1/3 on test piece EXA~PLE 3 -(Fungicidal test of printing paste) .
In a 500 ml beaker was placed 300 g of a printing paste as a solution of 1 wt.% wheat starch and 1 wt.~ of tragacanth gum. Each wettable powder prepared in Example 1 was incorporated in the prin-ting paste at a concentration of 1000 ppm or 2000 ppm of the active ingredient. The beaker was sealed with aluminum foil and kept in a constant temperature oven at 30DC. The growth of fungi on the surfaces of the printing pastes were observed. The results are shown in Table 3.
. . _ Concent~ Culturing time ration _ I ~ -Active ingredient (ppm) 4 day 7 day 10 day N-(2,4,6-trichloro- _ phenyl) 2000 _ _ maleimide 1000 _ _ _ -_ 2-(4-thiazoyl)-benzimidazol 2000 _ 1000 ~ ++ '":
tribu~yl-tin-oxide ~ _ . ~
Non-treatment ~ ++ ++
_ting:
-: no growth of fungi +: growth of fungi in area of less than 1/3 on surface in beaker ~,f~ 6 1 ~5960~
+ : growth of fungi in area of about 1/3 on surface in beaker -~: growth of fungi in area of more than 1/3 on surface in beaker.
(Fungicidal test of wall paper) Casein glue as an adhesive was prepared by boiling an aqueous solution of casein.
Each wettable concentrate of Example 1 was incorporated into the adhesive at a concentration of 2000 ppm of the active ingredient. The treated casein glue was used for bonding wall paper on a concrete having a thickness of 5 cm x 5 cm to ob-tain a test piece. The test piece was placed at a center of the plate culture medium made of 1000 ml of water, 40 g of glucose, 10 g of peptone and 25 g of arger in a Petri dish and a suspension of mixed spores of Aspergillus niger, Trichoderma viride, Pencillium citrinum and Rhizopus nigricans was uniformly sprayed in the Petri dish. The Petri dish was covered with a cover and kept in a constant temperature oven at 2~C for 15 days to culture it for 15 days. The results are shown in Table 4.
_ Culturing time Acti~e lngredient ~ day ¦ 10 day ~ 15 day N-(2,4,~-trichloro- _ _ _ phenyl) maleimide .
2-(4-thiazoyl)-ben- _ _ _ zimidazol _ _ tributyl-t~in-oxide _ +
Non-treatment L +-~+
~ `:
l 1~9~04 Rating:
- : no growth of fungi + : growth of fungi in area of less than 1/3 on surface in beaker + : growth of fungi in area of about 1/3 on surface in beaker ~-+: growth of fungi in area of more than 1/3 on surface in beaker Test 1. Funglcidal test of we-t pulp Each emulsifiable concentrate was prepared by mixing 20 wt. parts of each active ingredient, 10 wt. parts of a surfactant (~orpol 800 A: a trademark of Toho Kagaku K.~.), 5 wt. parts of a surfactant (Emulgen 800: a trademark of Kao-Atlas Co.), and 65 wt. parts of xylene. The emulsifiable concentrate was diluted with wa-ter to prepare each emulsion at a concentration of 200 ppm or 50 ppm of the active ingredient.
The emulsion was sprayed by a sprayer at a rate of 30 ml. per 1 kg of a we-t straw pulp! The treated pulp was held in a plastic film bag and kept in a constant temperature oven at 30C to observe the growth of fungi on the surface of wet pulp. The results are shown in Table 5.
The commercially available 2-(4-thiazoyl)benzimidazole was difficulty soluble to organic solvents whereby it could ;-not be emulsified to use it in the test.
TAsLE 5 Concent- Culturing time ration Active ingredient (ppm) 5 day 10 day 20 day _ : .
N-(2,4,6-trichloro- 1 200 _ _ _ phenyl) maleimide ¦ 50 _ _ tributyl-tin-oxide 200 _ _ +++
~ _ _ non-treatment _ ~ _ ++ +~+
:: ' l 15~60~
Test 2. Funyicidal test of wood:
Each emulsifiable concentrate of Test 1 was diluted with water to prepare each emulsion at a concentration of 200 ppm or 50 ppm of the active ingredient. Each pine wood chip (size of 5 cm x 5 cm x 30 cm) having a water content of 70 to 75% was dipped in the emulsion for 3 minutes. The treated pine wood was maintained in a chamber at 30C and a humidity of 80%.
The growth oE fungi on the wood chip was observed. The results are shown in Table 6.
The commercially available 2-(4-thiazoyl) benzimidazole was difficultly soluble in organic so]vents and it could not be emulsified for use in the Test.
_ _ _ _ Concent- Culturing time Active ingredient r(ppm)n 10 day .D d~ 30 day 1~-(2,4,6-trichloro- 200 _ _ _ phenyl)maleimide 50 _ _ _ __ ....
20 ~ L-t.in-oxi ~ ~ _ non-treatment L + ++ +++
::
9_
Claims (14)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method of preserving an industrial product or raw material against the action of fungi which comprises apply-ing thereto a fungicidally effective amount of N-(2,4,6-tri-chlorophenyl)maleimide.
2. A method according to claim 1, in which the maleimide is present in an aqueous emulsion paint or a water paint.
3. A method according to claim 1, in which the maleimide is present in an aqueous adhesive.
4. A method according to claim 1, in which the maleimide is present in a printing paste.
5. A method according to claim 1, in which the maleimide is present in a colloidal pulp slurry.
6. A method according to claim 1, 2 or 3, in which the maleimide is present in an amount of more than 100 ppm.
7. A method according to claim 1, 2 or 3, in which the maleimide is present in an amount of more than 200 ppm.
8. A fungicidal composition selected from an aqueous emulsion paint, a water paint, an aqueous adhesive, a printing paste and a colloidal pulp slurry, which contains a fungicidal-ly effective concentration of N-(2,4,6-trichlorophenyl)malei-mide.
9. The composition according to claim 8, which is an aqueous emulsion paint or a water paint.
10. The composition according to claim 8, which is an aqueous adhesive.
11. The composition according to claim 8, which is a printing paste.
12. The composition according to claim 8, which is a colloidal pulp slurry.
13. A composition according to claim 8, 9 or 10, containing more than 100 ppm of N-(2,4,6-trichlorophenyl)-maleimide.
14. A composition according to claim 8, 9 or 10, containing more than 200 ppm of N-(2,4,6-trichlorophenyl)-maleimide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14727479A JPS5671006A (en) | 1979-11-14 | 1979-11-14 | Industrial mildewcide |
| JP147274/1979 | 1979-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1159604A true CA1159604A (en) | 1984-01-03 |
Family
ID=15426498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000364517A Expired CA1159604A (en) | 1979-11-14 | 1980-11-12 | Aqueous slurry or pasty fungicidal composition |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5671006A (en) |
| CA (1) | CA1159604A (en) |
| DE (1) | DE3042337A1 (en) |
| FR (1) | FR2469123A1 (en) |
| GB (1) | GB2063069B (en) |
| NL (1) | NL8006036A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05664Y2 (en) * | 1988-03-18 | 1993-01-11 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3586697A (en) * | 1967-12-01 | 1971-06-22 | Sumitomo Chemical Co | Novel n-(3,5-dichlorophenyl) cyclic imide derivatives |
| JPS4938819A (en) * | 1972-08-17 | 1974-04-11 | ||
| US3890270A (en) * | 1974-04-10 | 1975-06-17 | Tenneco Chem | Polyvinyl halide resin compositions |
| JPS6017764B2 (en) * | 1976-07-10 | 1985-05-07 | イハラケミカル工業株式会社 | aquatic creature repellent |
-
1979
- 1979-11-14 JP JP14727479A patent/JPS5671006A/en active Granted
-
1980
- 1980-11-05 NL NL8006036A patent/NL8006036A/en not_active Application Discontinuation
- 1980-11-10 DE DE19803042337 patent/DE3042337A1/en not_active Withdrawn
- 1980-11-12 CA CA000364517A patent/CA1159604A/en not_active Expired
- 1980-11-12 FR FR8024062A patent/FR2469123A1/en active Granted
- 1980-11-14 GB GB8036579A patent/GB2063069B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2469123B1 (en) | 1985-05-17 |
| FR2469123A1 (en) | 1981-05-22 |
| DE3042337A1 (en) | 1981-05-21 |
| JPS6239123B2 (en) | 1987-08-21 |
| GB2063069A (en) | 1981-06-03 |
| JPS5671006A (en) | 1981-06-13 |
| GB2063069B (en) | 1983-03-16 |
| NL8006036A (en) | 1981-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5707929A (en) | Biocidal compositions comprising mixtures of haloproynyl compounds and sulfur containing triazines | |
| TW304862B (en) | ||
| KR20120071355A (en) | Synergistic combination of a glyphosate compound and zpt | |
| US5185357A (en) | Industrial antifungal composition | |
| KR20120071350A (en) | Synergistic combination of a glyphosate compound and ipbc | |
| US4303668A (en) | Antibacterial and antifungal composition | |
| US4341548A (en) | N-(2-Cyclohexylphenyl)-N',N'-diethyl-ethylene diamine, algicidal compositions containing same, and method of use | |
| US4323565A (en) | Antibacterial and antifungal composition | |
| CA1159604A (en) | Aqueous slurry or pasty fungicidal composition | |
| JPH06183914A (en) | Microbicidal composition for industrial use | |
| JPS6333307A (en) | Herbicidal method by use of diflufenican | |
| JPH07133206A (en) | Industrial preservative fungicide | |
| US4301162A (en) | Antibacterial and antifungal composition | |
| US4906648A (en) | Industrial antifungal composition | |
| KR20120071354A (en) | Synergistic combination of a glyphosate compound and tbz | |
| JPS6344121B2 (en) | ||
| US4272283A (en) | Herbicidal composition and method for controlling weeds | |
| JPS6054301A (en) | Antiseptic mildewproofing agent | |
| JPS6019704A (en) | Anticeptic mildewcide | |
| JPS5823843B2 (en) | Preservative and fungicide | |
| JP3195081B2 (en) | Industrial antiseptic / antifungal composition | |
| US4395274A (en) | Microbicidal agent and its use | |
| JP3604532B2 (en) | Antiseptic and fungicide | |
| JPH11269014A (en) | Industrial antiseptic and antifungal composition | |
| JPS5839124B2 (en) | Kogiyoyousatsukinsobutsu |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |