TW201103430A - Triazole compounds carrying a sulfur substituent XII - Google Patents

Triazole compounds carrying a sulfur substituent XII Download PDF

Info

Publication number: TW201103430A
Authority: TW; Taiwan
Prior art keywords: het; group; compound; formula; combination
Prior art date: 2009-06-18

Application number

TW099120001A

Other languages

English (en)

Chinese (zh)

Inventor

Sarah Ulmschneider

Jochen Dietz

Jens Renner

Thomas Grote

Wassilios Grammenos

Bernd Mueller

Jan Klaas Lohmann

Marianna Vrettou-Schultes

Original Assignee

Basf Se

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.)

2009-06-18

Filing date

2010-06-18

Publication date

2011-02-01

2010-06-18 Application filed by Basf Se filed Critical Basf Se

2011-02-01 Publication of TW201103430A publication Critical patent/TW201103430A/zh

Links

-1 Triazole compounds Chemical class 0.000 title claims abstract description 597
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 22
150000001875 compounds Chemical class 0.000 claims abstract description 946
239000000203 mixture Substances 0.000 claims abstract description 91
238000000034 method Methods 0.000 claims abstract description 43
125000000217 alkyl group Chemical group 0.000 claims description 137
239000002585 base Substances 0.000 claims description 105
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 93
125000001424 substituent group Chemical group 0.000 claims description 93
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
125000003545 alkoxy group Chemical group 0.000 claims description 74
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 66
125000000623 heterocyclic group Chemical group 0.000 claims description 46
125000005842 heteroatom Chemical group 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 42
239000007789 gas Substances 0.000 claims description 35
239000000463 material Substances 0.000 claims description 34
229920006395 saturated elastomer Polymers 0.000 claims description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
241000233866 Fungi Species 0.000 claims description 30
201000010099 disease Diseases 0.000 claims description 29
125000000304 alkynyl group Chemical group 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 27
229910052731 fluorine Inorganic materials 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
239000011737 fluorine Substances 0.000 claims description 25
229910052717 sulfur Inorganic materials 0.000 claims description 25
125000001188 haloalkyl group Chemical group 0.000 claims description 24
125000004438 haloalkoxy group Chemical group 0.000 claims description 23
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 23
125000003342 alkenyl group Chemical group 0.000 claims description 21
229910052794 bromium Inorganic materials 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
125000001072 heteroaryl group Chemical group 0.000 claims description 20
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 19
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 18
229910052707 ruthenium Inorganic materials 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
125000005347 halocycloalkyl group Chemical group 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
229910052751 metal Inorganic materials 0.000 claims description 14
239000002184 metal Substances 0.000 claims description 14
150000002923 oximes Chemical group 0.000 claims description 14
239000002689 soil Substances 0.000 claims description 14
125000001931 aliphatic group Chemical group 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 13
125000000000 cycloalkoxy group Chemical group 0.000 claims description 13
125000004076 pyridyl group Chemical group 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
239000007787 solid Substances 0.000 claims description 12
239000011593 sulfur Substances 0.000 claims description 12
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 11
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 10
125000002837 carbocyclic group Chemical group 0.000 claims description 10
125000000232 haloalkynyl group Chemical group 0.000 claims description 10
125000002971 oxazolyl group Chemical group 0.000 claims description 10
150000001721 carbon Chemical group 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 9
229910052783 alkali metal Inorganic materials 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000005133 alkynyloxy group Chemical group 0.000 claims description 8
150000001768 cations Chemical class 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000000168 pyrrolyl group Chemical group 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
150000003573 thiols Chemical class 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
125000003302 alkenyloxy group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
125000004149 thio group Chemical group *S* 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
125000005109 alkynylthio group Chemical group 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
125000000262 haloalkenyl group Chemical group 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
206010028980 Neoplasm Diseases 0.000 claims description 5
239000005864 Sulphur Substances 0.000 claims description 5
150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
201000011510 cancer Diseases 0.000 claims description 5
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
125000001425 triazolyl group Chemical group 0.000 claims description 5
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 4
125000004103 aminoalkyl group Chemical group 0.000 claims description 4
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000006612 decyloxy group Chemical group 0.000 claims description 4
125000005291 haloalkenyloxy group Chemical group 0.000 claims description 4
125000004995 haloalkylthio group Chemical group 0.000 claims description 4
125000006769 halocycloalkoxy group Chemical group 0.000 claims description 4
125000001786 isothiazolyl group Chemical group 0.000 claims description 4
229910052762 osmium Inorganic materials 0.000 claims description 4
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
239000004575 stone Substances 0.000 claims description 4
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
230000002538 fungal effect Effects 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
125000004354 sulfur functional group Chemical group 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
244000053095 fungal pathogen Species 0.000 claims description 2
208000015181 infectious disease Diseases 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
230000001850 reproductive effect Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
241000283973 Oryctolagus cuniculus Species 0.000 claims 1
208000003251 Pruritus Diseases 0.000 claims 1
208000036142 Viral infection Diseases 0.000 claims 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 1
150000004056 anthraquinones Chemical class 0.000 claims 1
125000005366 cycloalkylthio group Chemical group 0.000 claims 1
LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical group C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
244000000008 fungal human pathogen Species 0.000 claims 1
125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 claims 1
150000002926 oxygen Chemical class 0.000 claims 1
230000001717 pathogenic effect Effects 0.000 claims 1
125000002071 phenylalkoxy group Chemical group 0.000 claims 1
125000003884 phenylalkyl group Chemical group 0.000 claims 1
230000009385 viral infection Effects 0.000 claims 1
239000000417 fungicide Substances 0.000 abstract description 17
239000000460 chlorine Chemical group 0.000 description 201
241000196324 Embryophyta Species 0.000 description 88
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 66
239000013543 active substance Substances 0.000 description 58
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 33
206010057190 Respiratory tract infections Diseases 0.000 description 31
240000008042 Zea mays Species 0.000 description 31
235000002017 Zea mays subsp mays Nutrition 0.000 description 30
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235000005822 corn Nutrition 0.000 description 27
235000013399 edible fruits Nutrition 0.000 description 26
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
235000010469 Glycine max Nutrition 0.000 description 24
108090000623 proteins and genes Proteins 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
240000007594 Oryza sativa Species 0.000 description 23
235000007164 Oryza sativa Nutrition 0.000 description 23
235000021307 Triticum Nutrition 0.000 description 23
241000209140 Triticum Species 0.000 description 23
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
102000004169 proteins and genes Human genes 0.000 description 21
239000002904 solvent Substances 0.000 description 21
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 20
239000002253 acid Chemical class 0.000 description 19
239000003053 toxin Substances 0.000 description 19
240000005979 Hordeum vulgare Species 0.000 description 17
235000007340 Hordeum vulgare Nutrition 0.000 description 17
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 17
231100000765 toxin Toxicity 0.000 description 17
108700012359 toxins Proteins 0.000 description 17
235000013311 vegetables Nutrition 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 15
239000000049 pigment Substances 0.000 description 15
239000000839 emulsion Substances 0.000 description 14
230000000855 fungicidal effect Effects 0.000 description 14
150000002431 hydrogen Chemical group 0.000 description 14
125000004434 sulfur atom Chemical group 0.000 description 14
229910052760 oxygen Inorganic materials 0.000 description 13
239000001301 oxygen Substances 0.000 description 13
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235000004977 Brassica sinapistrum Nutrition 0.000 description 12
235000021536 Sugar beet Nutrition 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000000047 product Substances 0.000 description 12
235000002595 Solanum tuberosum Nutrition 0.000 description 11
244000061456 Solanum tuberosum Species 0.000 description 11
150000002576 ketones Chemical class 0.000 description 11
230000008569 process Effects 0.000 description 11
230000001568 sexual effect Effects 0.000 description 11
239000011734 sodium Substances 0.000 description 11
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
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YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
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229910052708 sodium Inorganic materials 0.000 description 10
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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239000003981 vehicle Substances 0.000 description 1
239000002578 wasp venom Substances 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
239000004549 water soluble granule Substances 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1
241000228158 x Triticosecale Species 0.000 description 1
FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

TW099120001A 2009-06-18 2010-06-18 Triazole compounds carrying a sulfur substituent XII TW201103430A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP09163172		2009-06-18

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TW201103430A true TW201103430A (en)	2011-02-01

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AR (1)	AR077153A1 (es)
TW (1)	TW201103430A (es)
UY (1)	UY32725A (es)
WO (1)	WO2010146116A1 (es)

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2010
- 2010-06-17 WO PCT/EP2010/058541 patent/WO2010146116A1/en not_active Ceased
- 2010-06-18 AR ARP100102177A patent/AR077153A1/es unknown
- 2010-06-18 TW TW099120001A patent/TW201103430A/zh unknown
- 2010-06-18 UY UY0001032725A patent/UY32725A/es unknown

Also Published As

Publication number	Publication date
WO2010146116A1 (en)	2010-12-23
AR077153A1 (es)	2011-08-03
UY32725A (es)	2010-12-31

Publication	Publication Date	Title
US20120088663A1 (en)	2012-04-12	Triazole Compounds Carrying a Sulfur Substituent
US20120088664A1 (en)	2012-04-12	Antifungal 1,2,4-triazolyl derivatives having a 5-sulfur subtituent
TW201103430A (en)	2011-02-01	Triazole compounds carrying a sulfur substituent XII
US20120077676A1 (en)	2012-03-29	Antifungal 1,2,4-Triazolyl Derivatives Having a 5-Sulfur Substituent
US20120088660A1 (en)	2012-04-12	Antifungal 1,2,4-triazolyl Derivatives
TW201103429A (en)	2011-02-01	Triazole compounds carrying a sulfur substituent XI
US10696634B2 (en)	2020-06-30	Pyridine compounds as fungicides
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