JP2012511543A - 4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1h−ピロール−3−カルボニトリルを含んでなる防汚性組み合わせ - Google Patents
4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1h−ピロール−3−カルボニトリルを含んでなる防汚性組み合わせ Download PDFInfo
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- JP2012511543A JP2012511543A JP2011540094A JP2011540094A JP2012511543A JP 2012511543 A JP2012511543 A JP 2012511543A JP 2011540094 A JP2011540094 A JP 2011540094A JP 2011540094 A JP2011540094 A JP 2011540094A JP 2012511543 A JP2012511543 A JP 2012511543A
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- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
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- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960005137 succinic acid Drugs 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
- A61L2/18—Liquid substances or solutions comprising solids or dissolved gases
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Hydrology & Water Resources (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
Abstract
Description
−工業用水性プロセス液(industrial aqueous process fluid)、例えば冷却水、パルプ及び製紙ミルプロセス水及びサスペンジョン(suspensions)、二次油回収システム、紡糸液、金属工作液など
−水性機能液のイン−タンク/イン−カン(in−tank/in−can)保護、例え
ばポリマーエマルジョン、水に基づく塗料及び接着剤、グルー(glues)、デンプンスラリ、増粘剤溶液、ゼラチン、ワックスエマルジョン、インキ、艶出剤、顔料及び鉱物性スラリ(mineral slurries)、ゴムラテックス、コンクリート添加剤、掘削泥(drilling mud’s)、洗面用品(toiletries)、水性化粧用調製物、製薬学的調製物など。
rubra)を含む二枚貝;エレクトラ・ピロサ(Electra pilosa)、ブグラ・ネリチナ(Bugula neritina)及びボウェルバンキア・グラシリス(Bowelbankia gracilis)を含む苔虫類(bryozoans);ヒドロイデス・ノルベジカ(Hydroides norvegica)を含む多毛虫;海綿動物;ならびにアルテミア(Artemia)及びツルアシ類(Cirripedia)(フジツボ(barnacles))を含む甲殻類の綱のメンバー、例えばバラヌス・アンフィツリテ(Balanus amphitrite)、レパス・アナチフェラ(Lepas anatifera)、バラヌス・バラヌス(Balanus balanus)、バラヌス・バラノイデス(Balanus balanoides)、バラヌス・ハメリ(Balanus hameri)、バラヌス・クレナツス(Balanus
crenatus)、バラヌス・インプロビスス(Balanus improvisus)、バラヌス・ガレアツス(Balanus galeatus)及びバラヌス・エブルネウス(Balanus eburneus);ならびにエルミニウス・モデスツス(Elminius modestus)及びハナカゴ(Verruca)である。
れるべき基質に依存して、組成物中の成分(I)及び(II)の様々な割合内で該相乗的効果を得ることができる。本出願の記述に基づき、実験1に記載される毒プレートアッセイ(Poison Plate Assay)の方法に従って、そのような組み合わせの相乗的効果の決定を行うことができる。しかしながら一般に、ほとんどの汚染生物の場合に、組成物中の成分(I)の量対成分(II)の量の重量による適した割合は、10:1〜1:10の範囲内に含まれるべきであると言うことができる。特にこの範囲は8:2〜2:8であり、より特定的に3:1〜1:3又は2:1〜1:2である。本発明の組成物中の成分(I)対成分(II)の別の特定の比は、成分(I)及び成分(II)の間の1:1の比である。
ば水、アルコール(例えばメチルアルコール、エチルアルコール、エチレングリコール、プロピレングリコール、ジエチレングリコール、グリセリンなど)、ケトン(例えばアセトン、メチルエチルケトンなど)、エーテル(例えばジオキサン、テトラヒドロフラン、セロソルブ、ジエチレングリコールジメチルエーテルなど)、脂肪族炭化水素(例えばヘキサン、ケロセンなど)、芳香族炭化水素(例えばベンゼン、トルエン、キシレン、ソルベントナフサ、メチルナフタレンなど)、ハロゲン化炭化水素(例えばクロロホルム、四塩化炭素など)、酸アミド(例えばジメチルホルムアミドなど)、エステル(例えば酢酸メチルエステル、酢酸エチルエステル、酢酸ブチルエステル、脂肪酸グリセリンエステルなど)ならびにニトリル(例えばアセトニトリルなど)である。これらの溶剤を単独で、又は2種もしくはそれより多くの組み合わせにおいて用いることができる。
ン中の防汚添加剤として用いることができる。架橋ポリウレタンへの添加のために、該成分(I)及び(II)の組み合わせをポリオール成分に、それをイソシアナート成分と反応させる前に加えることができる。溶融−加工される熱可塑性ポリウレタンへの添加のために、該成分(I)及び(II)の組み合わせを溶融物中に、例えば押出し系における注入点において量り込むことができる。あるいはまた、濃厚形態における防汚添加剤を含有するポリマー顆粒又はチップを製造することもできる。これらを、殺生物剤(biocide)を含有しないポリマー顆粒又はチップと配合し、次いで押出しを介してさらに熱加工することができる。
−(a)成分(I)として4−ブロモ−2−(4−クロロ−フェニル)−5−(トリフルオロメチル)−1H−ピロール−3−カルボニトリル又はその塩を含んでなる組成物及び−(b)成分(II)として2−ブチル−1,2−ベンズイソチアゾール−3(2H)オン又はその塩を含んでなる組成物
を同時もしくは逐次的使用のための組み合わせとして含有する製品も包含し、ここで該(a)及び(b)は汚染生物に対する相乗的効果を与えるそれぞれの割合にある。
実験1:毒プレートアッセイ
一般的方法:24−ウェルミクロタイタープレート(microtiter plate)の各ウェルに、用量系列の1つの濃度における試験化合物を含有する1990μlのBG11培地を加える。活発に成長している3週令の藻類の液体BG11培養物のアリコートを加えることにより、液体淡水無機培地(liquid freshwater mineral medium)に接種し、21℃、65%相対湿度、1000Lux16時間/日においてインキュベーションする。2週間後に成長を評価する。
(トリフルオロメチル)−1H−ピロール−3−カルボニトリル
成分(II)としてブチルBIT
倍液: DMSO中の8000及び80.000ppm
試験的組み合わせ:%生成物A + %生成物B
100 + 0
80 + 20
66 + 33
50 + 50
33 + 66
20 + 80
0 + 100
濃度: 1.6−1.2−0.9−0.68−0.51−0.38−0.29
−0.21−0.16−0.12−0.09−0.07ppm
培地: 藻類:BG11液体無機培地(liquid mineral me
dium)
実験装置: 24−ウェルプレート
藻類の種: ツリボネマ種(Tribonema sp.) CCAP880/2接種: 藻類:2週令培養物のBG11中の1/10希釈の1990μl
培養条件: 21℃,65%相対湿度,1000lux,16時間明期
評価: 藻類:2週間の暴露後
・QAは、終点を生ずる単独で作用する化合物Aのppmにおける濃度(例えばMIC)であり、
・Qaは、終点を生ずる混合物における化合物Aのppmにおける濃度(例えばMIC)であり、
・QBは、終点を生ずる単独で作用する化合物Bのppmにおける濃度(例えばMIC)であり、
・Qbは、終点を生ずる混合物における化合物Bのppmにおける濃度(例えばMIC)である。
Claims (8)
- 成分(I)としての4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1H−ピロール−3−カルボニトリル又はその塩の成分(II)としての2−ブチル−1,2−ベンズイソチアゾール−3(2H)オン又はその塩と一緒の組み合わせを含んでなり、ここで成分(I)及び成分(II)は、汚染生物に対する相乗的効果を与えるそれぞれの割合で存在する組成物。
- 成分(I)対成分(II)の重量比が10:1〜1:10である請求項1に記載の組成物。
- 成分(I)対成分(II)の重量比が3:1〜1:3である請求項2に記載の組成物。
- 成分(I)の量が組成物の合計重量に基づいて1重量%〜40重量%の範囲である請求項1〜3のいずれかに記載の組成物。
- 汚染生物の抑制のための請求項1〜4のいずれかに記載の組成物の使用。
- 請求項1〜4のいずれかに記載の組成物の防汚有効量の投与又は適用を含んでなる、汚染生物に対する材料の保護方法。
- 請求項1〜4のいずれかに記載の組成物の防汚的に有効な量を加えることにより、バラスト水を殺菌する方法。
- (a)成分(I)として4−ブロモ−2−(4−クロロ−フェニル)−5−(トリフルオロメチル)−1H−ピロール−3−カルボニトリル又はその塩を含んでなる組成物、及び
(b)成分(II)として2−ブチル−1,2−ベンズイソチアゾール−3(2H)オン又はその塩を含んでなる組成物
を同時もしくは逐次的使用のための組み合わせとして含有し、ここで該(a)及び(b)は汚染生物に対する相乗的効果を与えるそれぞれの割合で存在する製品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP08171273 | 2008-12-11 | ||
EP08171273.9 | 2008-12-11 | ||
PCT/EP2009/066796 WO2010066825A1 (en) | 2008-12-11 | 2009-12-10 | Antifouling combination comprising 4 bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile |
Publications (2)
Publication Number | Publication Date |
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JP2012511543A true JP2012511543A (ja) | 2012-05-24 |
JP5433017B2 JP5433017B2 (ja) | 2014-03-05 |
Family
ID=40566134
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JP2011540094A Active JP5433017B2 (ja) | 2008-12-11 | 2009-12-10 | 4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1h−ピロール−3−カルボニトリルを含んでなる防汚性組み合わせ |
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US (1) | US20110237632A1 (ja) |
EP (1) | EP2375902A1 (ja) |
JP (1) | JP5433017B2 (ja) |
KR (1) | KR101675099B1 (ja) |
CN (1) | CN102245026B (ja) |
SG (1) | SG172099A1 (ja) |
TW (1) | TW201033308A (ja) |
WO (1) | WO2010066825A1 (ja) |
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EP1446011B1 (en) * | 2001-11-08 | 2009-01-14 | Janssen Pharmaceutica N.V. | Synergistic antifouling compositions comprising 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile |
BR122016012079B1 (pt) | 2006-02-01 | 2023-01-24 | Janssen Pharmaceutica N.V | Composições compreendendo uma combinação de 4-bromo-2-(4-clorofenil)-5-(trifluorometil)-1h-pirrol-3-carbonitrila com composto de zinco e seus usos |
WO2007116051A1 (en) * | 2006-04-10 | 2007-10-18 | Janssen Pharmaceutica N.V. | Combinations of 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile and biocidal compounds |
WO2008017656A2 (en) * | 2006-08-07 | 2008-02-14 | Janssen Pharmaceutica Nv | Combinations of 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1 h-pyrrole-3-carbonitrile and oxidizing agents |
WO2012001027A2 (en) * | 2010-07-01 | 2012-01-05 | Janssen Pharmaceutica Nv | Antifouling benzoate combinations |
RU2609373C2 (ru) * | 2012-03-07 | 2017-02-01 | Янссен Фармацевтика Нв | Применение тралопирила против морских древоточцев |
CN104230916B (zh) * | 2014-09-30 | 2020-04-28 | 上海化学试剂研究所有限公司 | 一种异噻唑啉酮类化合物及其制备方法和应用 |
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JPH092908A (ja) * | 1995-05-23 | 1997-01-07 | American Cyanamid Co | 防汚剤としてのピロール化合物の使用 |
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JP2001503789A (ja) * | 1996-09-19 | 2001-03-21 | シグマ・コーテイングズ・ベー・ブイ | 明るい色及び鮮明な色の防汚塗料 |
JP2005507429A (ja) * | 2001-11-08 | 2005-03-17 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1h−ピロール−3−カルボニトリルを含む相乗性防汚組成物 |
JP2009525307A (ja) * | 2006-02-01 | 2009-07-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1h−ピロール−3−カルボニトリルおよび金属化合物の組み合わせ物 |
JP2009528356A (ja) * | 2006-03-03 | 2009-08-06 | アーチ・ケミカルズ・インコーポレーテッド | ピリチオンおよびピロール誘導体を含む殺生剤組成物 |
JP2009533384A (ja) * | 2006-04-10 | 2009-09-17 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1h−ピロール−3−カルボニトリルおよび殺生物性化合物の組み合わせ |
JP2012505176A (ja) * | 2008-10-08 | 2012-03-01 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 殺生物剤を含んでなるハイソリッド分散液 |
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DE102005045129A1 (de) * | 2005-09-21 | 2007-03-22 | Schülke & Mayr GmbH | Zubereitung zur fungiziden und algiziden Ausrüstung alkalischer Beschichtungszusammensetzungen |
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JPH092908A (ja) * | 1995-05-23 | 1997-01-07 | American Cyanamid Co | 防汚剤としてのピロール化合物の使用 |
JP2001503789A (ja) * | 1996-09-19 | 2001-03-21 | シグマ・コーテイングズ・ベー・ブイ | 明るい色及び鮮明な色の防汚塗料 |
JPH10298012A (ja) * | 1997-04-22 | 1998-11-10 | Takeda Chem Ind Ltd | 殺微生物剤組成物および微生物防除方法 |
JP2005507429A (ja) * | 2001-11-08 | 2005-03-17 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1h−ピロール−3−カルボニトリルを含む相乗性防汚組成物 |
JP2009525307A (ja) * | 2006-02-01 | 2009-07-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1h−ピロール−3−カルボニトリルおよび金属化合物の組み合わせ物 |
JP2009528356A (ja) * | 2006-03-03 | 2009-08-06 | アーチ・ケミカルズ・インコーポレーテッド | ピリチオンおよびピロール誘導体を含む殺生剤組成物 |
JP2009533384A (ja) * | 2006-04-10 | 2009-09-17 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 4−ブロモ−2−(4−クロロフェニル)−5−(トリフルオロメチル)−1h−ピロール−3−カルボニトリルおよび殺生物性化合物の組み合わせ |
JP2012505176A (ja) * | 2008-10-08 | 2012-03-01 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 殺生物剤を含んでなるハイソリッド分散液 |
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TW201033308A (en) | 2010-09-16 |
JP5433017B2 (ja) | 2014-03-05 |
KR101675099B1 (ko) | 2016-11-10 |
CN102245026B (zh) | 2014-08-06 |
SG172099A1 (en) | 2011-07-28 |
CN102245026A (zh) | 2011-11-16 |
US20110237632A1 (en) | 2011-09-29 |
KR20110098939A (ko) | 2011-09-02 |
WO2010066825A1 (en) | 2010-06-17 |
EP2375902A1 (en) | 2011-10-19 |
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