IL100288A - Method and preparations containing certain triazoles to protect substances against fungal attack - Google Patents

Method and preparations containing certain triazoles to protect substances against fungal attack

Info

Publication number: IL100288A
Authority: IL; Israel
Prior art keywords: triazole; propanenitrile; alpha; phenyl; butyl
Prior art date: 1990-12-10

Application number

IL10028891A

Other languages

English (en)

Hebrew (he)

Other versions

IL100288A0 (en

Original Assignee

Rohm & Haas

Priority date (The priority date 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 date listed.)

1990-12-10

Filing date

1991-12-09

Publication date

1995-12-31

1991-12-09 Application filed by Rohm & Haas filed Critical Rohm & Haas

1992-09-06 Publication of IL100288A0 publication Critical patent/IL100288A0/xx

1995-12-31 Publication of IL100288A publication Critical patent/IL100288A/en

Links

150000003852 triazoles Chemical class 0.000 title claims abstract description 45
239000000203 mixture Substances 0.000 title claims abstract description 19
238000000034 method Methods 0.000 title claims description 9
239000000463 material Substances 0.000 title abstract description 8
230000002538 fungal effect Effects 0.000 title description 11
239000002023 wood Substances 0.000 claims abstract description 10
150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 8
241000233866 Fungi Species 0.000 claims abstract description 7
238000000576 coating method Methods 0.000 claims abstract description 4
239000004744 fabric Substances 0.000 claims abstract description 4
239000010985 leather Substances 0.000 claims abstract description 4
230000012010 growth Effects 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
230000002411 adverse Effects 0.000 claims description 2
239000003429 antifungal agent Substances 0.000 claims description 2
229940121375 antifungal agent Drugs 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims 3
230000000855 fungicidal effect Effects 0.000 abstract description 7
239000000417 fungicide Substances 0.000 abstract description 2
DUAWLKDRICEPJW-UHFFFAOYSA-N 2,2-diphenyl-3-(1,2,4-triazol-1-yl)propanenitrile Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C#N)CN1C=NC=N1 DUAWLKDRICEPJW-UHFFFAOYSA-N 0.000 abstract 1
JPNUVXSIDDEFGI-UHFFFAOYSA-N 2,4-diphenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=NC=NN1CC(C=1C=CC=CC=1)(C#N)CCC1=CC=CC=C1 JPNUVXSIDDEFGI-UHFFFAOYSA-N 0.000 abstract 1
HRVMTBFBTHMNEH-UHFFFAOYSA-N 2-(2-methoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=CC=C(OC)C=1C(CCCC)(C#N)CN1C=NC=N1 HRVMTBFBTHMNEH-UHFFFAOYSA-N 0.000 abstract 1
HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 abstract 1
CVAWIFGMSAVHGA-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(F)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 CVAWIFGMSAVHGA-UHFFFAOYSA-N 0.000 abstract 1
CPEODECDVMFSPI-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-(1,2,4-triazol-1-ylmethyl)pentanenitrile Chemical compound C=1C=C(F)C=CC=1C(CCC)(C#N)CN1C=NC=N1 CPEODECDVMFSPI-UHFFFAOYSA-N 0.000 abstract 1
RJYPYIUENVDJRA-UHFFFAOYSA-N 2-benzyl-2-phenyl-3-(1,2,4-triazol-1-yl)propanenitrile Chemical compound C1=NC=NN1CC(C=1C=CC=CC=1)(C#N)CC1=CC=CC=C1 RJYPYIUENVDJRA-UHFFFAOYSA-N 0.000 abstract 1
WSBXOYCTBXULGP-UHFFFAOYSA-N 2-phenyl-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=CC=CC=1C(CCCC)(C#N)CN1C=NC=N1 WSBXOYCTBXULGP-UHFFFAOYSA-N 0.000 abstract 1
RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 abstract 1
238000012360 testing method Methods 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
239000001965 potato dextrose agar Substances 0.000 description 10
239000003973 paint Substances 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000028644 hyphal growth Effects 0.000 description 6
238000003359 percent control normalization Methods 0.000 description 6
239000004816 latex Substances 0.000 description 5
229920000126 latex Polymers 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 4
241000228245 Aspergillus niger Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
239000000049 pigment Substances 0.000 description 3
230000002195 synergetic effect Effects 0.000 description 3
DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
241000221832 Amorphotheca resinae Species 0.000 description 2
241000228197 Aspergillus flavus Species 0.000 description 2
241000223678 Aureobasidium pullulans Species 0.000 description 2
229940126062 Compound A Drugs 0.000 description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
239000008272 agar Substances 0.000 description 2
239000000084 colloidal system Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
-1 poly(methacrylic acid) Polymers 0.000 description 2
239000000243 solution Substances 0.000 description 2
241000894007 species Species 0.000 description 2
239000000126 substance Substances 0.000 description 2
NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 1
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
241000213004 Alternaria solani Species 0.000 description 1
241000766700 Coniochaeta mutabilis Species 0.000 description 1
206010061619 Deformity Diseases 0.000 description 1
241000223221 Fusarium oxysporum Species 0.000 description 1
241000233732 Fusarium verticillioides Species 0.000 description 1
241000123332 Gloeophyllum Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
241001314546 Microtis <orchid> Species 0.000 description 1
241001507673 Penicillium digitatum Species 0.000 description 1
241000122123 Penicillium italicum Species 0.000 description 1
241001492489 Postia placenta Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000005822 Propiconazole Substances 0.000 description 1
229920001218 Pullulan Polymers 0.000 description 1
240000003192 Rhynchospora rubra Species 0.000 description 1
229920013802 TRITON CF-10 Polymers 0.000 description 1
241000222355 Trametes versicolor Species 0.000 description 1
241000223261 Trichoderma viride Species 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
238000003556 assay Methods 0.000 description 1
AKNQMEBLVAMSNZ-UHFFFAOYSA-N azaconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 AKNQMEBLVAMSNZ-UHFFFAOYSA-N 0.000 description 1
229950000294 azaconazole Drugs 0.000 description 1
150000003851 azoles Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
235000019423 pullulan Nutrition 0.000 description 1
235000019832 sodium triphosphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
239000001974 tryptic soy broth Substances 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1

Classifications

- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/345—Nitriles
- D06M13/348—Nitriles unsaturated, e.g. acrylonitrile
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/352—Heterocyclic compounds having five-membered heterocyclic rings
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines

Landscapes

Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Life Sciences & Earth Sciences (AREA)
Plant Pathology (AREA)
Dentistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Treatment And Processing Of Natural Fur Or Leather (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL10028891A 1990-12-10 1991-12-09 Method and preparations containing certain triazoles to protect substances against fungal attack IL100288A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/625,278 US5223178A (en)	1990-12-10	1990-12-10	Use of certain triazoles to protect materials from fungal attack, articles and compositions

Publications (2)

Publication Number	Publication Date
IL100288A0 IL100288A0 (en)	1992-09-06
IL100288A true IL100288A (en)	1995-12-31

Family

ID=24505348

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10028891A IL100288A (en)	1990-12-10	1991-12-09	Method and preparations containing certain triazoles to protect substances against fungal attack

Country Status (15)

Country	Link
US (1)	US5223178A (de)
EP (1)	EP0490563B1 (de)
JP (1)	JP3114946B2 (de)
AT (1)	ATE128811T1 (de)
BR (1)	BR9105308A (de)
CA (1)	CA2055357A1 (de)
DE (1)	DE69113762T2 (de)
DK (1)	DK0490563T3 (de)
ES (1)	ES2079588T3 (de)
GR (1)	GR3017732T3 (de)
HU (1)	HUT59565A (de)
IL (1)	IL100288A (de)
MX (1)	MX9102486A (de)
MY (1)	MY107016A (de)
NZ (1)	NZ240871A (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9116672D0 (en) *	1991-08-01	1991-09-18	Hickson Int Plc	Preservatives for wood and other cellulosic materials
WO1993002557A1 (en) *	1991-08-01	1993-02-18	Hickson International Plc	Preservatives for wood and other cellulosic materials
US5358939A (en) *	1992-06-25	1994-10-25	Rohm And Haas Company	Fungicidal 2-aryl-2,2-disubstituted ethyl-1,2,4-triazoles
EP0917425A1 (de) *	1995-12-20	1999-05-26	Nigel Paul Maynard	Lösen von bioziden mittels wasserfreier onium-verbindungen als lösungsmittel
DE19648888A1 (de) *	1996-11-26	1998-05-28	Remmers Bauchemie Gmbh	Wasserverdünnbares Konzentrat für den Holzschutz
DE10218482A1 (de) *	2002-04-25	2003-11-20	Sto Ag	Mittel zur Behandlung von mit Algen und/oder Pilzen befallenen Flächen
DE10360836A1 (de) *	2003-12-23	2005-07-21	Bayer Chemicals Ag	Mittel zum Schutz von technischen Materialien
GB2438404A (en) *	2006-05-24	2007-11-28	Arch Timber Protection Ltd	Preserving wood with an amine oxide, an azole and a specified amine or quaternary ammonium compound, in synergistic proportions

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4366165A (en) *	1977-05-19	1982-12-28	Rohm And Haas Company	1 and 4-Arylcyanoalkyl-1,2,4-triazoles and fungicidal use
IL55203A (en) *	1978-07-23	1982-08-31	Yeda Res & Dev	Antifouling paints containing sulfone derivatives
NZ196075A (en) *	1980-02-04	1982-12-07	Janssen Pharmaceutica Nv	Agent to protect wood coatings and detergents from micro-organisms using a triazole
NZ198085A (en) *	1980-08-18	1985-09-13	Ici Plc	Regulation of plant growth with certain 2,2-di(hydrocarbyl)-1-(1,2,4-triazol-1-yl)ethan-2-ols
EP0061840A3 (de) *	1981-03-30	1983-08-24	Imperial Chemical Industries Plc	Triazolverbindungen, Verfahren zu deren Herstellung, deren Anwendung als Pflanzenfungizide und deren fungizide Zusammensetzungen
JPS59104367A (ja) *	1982-12-03	1984-06-16	Takeda Chem Ind Ltd	トリアゾ−ル誘導体，その製造法及び植物生長調整剤
GR80284B (en) *	1983-09-06	1985-01-07	Du Pont	Fungicidal triazole and imidazole compounds
US4920139A (en) *	1983-11-10	1990-04-24	Rohm And Haas Company	Alpha-alkyl-alpha-(4-halophenyl)-1H-1,2,4-triazole-1-propanenitrile
CA1227801A (en) *	1983-11-10	1987-10-06	Ted T. Fujimoto	.alpha.-ALKYL-.alpha.-(4-HALOPHENYL)-1H-1,2,4-TRIAZOLE-1- PROPANENITRILES
US4648988A (en) *	1983-12-21	1987-03-10	Janssen Pharmaceutica, N.V.	Water-dilutable wood-preserving liquids
GB8429932D0 (en) *	1984-11-27	1985-01-03	Pfizer Ltd	Triazole antifungal agents
US4677003A (en) *	1985-04-30	1987-06-30	Rohm And Haas Company	Microsuspension process for preparing solvent core sequential polymer dispersion
US4895865A (en) *	1986-01-10	1990-01-23	Rohm And Haas Company	Alpha-(2-alkoxyphenyl)-alpha-alkyl-1H-1,2,4-triazole-1-propanenitriles and derivatives
GB8612796D0 (en) *	1986-05-27	1986-07-02	Fbc Ltd	Fungicides
CA1321588C (en) *	1986-07-02	1993-08-24	Katherine Eleanor Flynn	Alpha-aryl-alpha-phenylethyl-1h-1,2,4-triazole-1- propanenitriles
FR2626740B1 (fr) *	1988-02-08	1990-10-19	Xylochimie	Concentres emulsionnables de matieres biocides, les microemulsions aqueuses obtenues et l'application de ces microemulsions au traitement du bois
US5102898A (en) *	1989-11-09	1992-04-07	Rohm And Haas Company	Benzoxazolone compounds and the use thereof as microbicides

1990
- 1990-12-10 US US07/625,278 patent/US5223178A/en not_active Expired - Fee Related
1991
- 1991-11-13 CA CA002055357A patent/CA2055357A1/en not_active Abandoned
- 1991-12-04 AT AT91311266T patent/ATE128811T1/de not_active IP Right Cessation
- 1991-12-04 EP EP91311266A patent/EP0490563B1/de not_active Expired - Lifetime
- 1991-12-04 DE DE69113762T patent/DE69113762T2/de not_active Expired - Fee Related
- 1991-12-04 ES ES91311266T patent/ES2079588T3/es not_active Expired - Lifetime
- 1991-12-04 MY MYPI91002245A patent/MY107016A/en unknown
- 1991-12-04 DK DK91311266.0T patent/DK0490563T3/da active
- 1991-12-05 NZ NZ240871A patent/NZ240871A/en unknown
- 1991-12-09 IL IL10028891A patent/IL100288A/en not_active IP Right Cessation
- 1991-12-10 JP JP03350041A patent/JP3114946B2/ja not_active Expired - Fee Related
- 1991-12-10 HU HU913882A patent/HUT59565A/hu unknown
- 1991-12-10 BR BR919105308A patent/BR9105308A/pt not_active Application Discontinuation
- 1991-12-10 MX MX9102486A patent/MX9102486A/es not_active IP Right Cessation
1995
- 1995-10-12 GR GR950402689T patent/GR3017732T3/el unknown

Also Published As

Publication number	Publication date
DE69113762T2 (de)	1996-05-02
US5223178A (en)	1993-06-29
HUT59565A (en)	1992-06-29
EP0490563B1 (de)	1995-10-11
EP0490563A1 (de)	1992-06-17
HU913882D0 (en)	1992-02-28
MX9102486A (es)	1992-06-01
DE69113762D1 (de)	1995-11-16
NZ240871A (en)	1995-07-26
DK0490563T3 (da)	1995-11-27
GR3017732T3 (en)	1996-01-31
ES2079588T3 (es)	1996-01-16
JP3114946B2 (ja)	2000-12-04
BR9105308A (pt)	1992-08-18
MY107016A (en)	1995-08-30
JPH0558813A (ja)	1993-03-09
IL100288A0 (en)	1992-09-06
CA2055357A1 (en)	1992-06-11
ATE128811T1 (de)	1995-10-15

Legal Events

Date	Code	Title	Description
1996-06-18	FF	Patent granted
1998-12-06	RH	Patent void

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