TW200932116A - Azolylmethyloxiranes, their use and compositions comprising them - Google Patents

Azolylmethyloxiranes, their use and compositions comprising them Download PDF

Info

Publication number: TW200932116A
Authority: TW; Taiwan
Prior art keywords: compound; group; case; columns; alkyl
Prior art date: 2007-12-19

Application number

TW097149852A

Other languages

English (en)

Chinese (zh)

Inventor

Jens Renner

Thomas Grote

Bernd Mueller

Sarah Ulmschneider

Alice Glaettli

Jochen Dietz

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.)

2007-12-19

Filing date

2008-12-19

Publication date

2009-08-01

2008-12-19 Application filed by Basf Se filed Critical Basf Se

2009-08-01 Publication of TW200932116A publication Critical patent/TW200932116A/zh

Links

239000000203 mixture Substances 0.000 title claims description 14
ZFOWEXGOKLKOFQ-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-1h-pyrrole Chemical class C=1C=CNC=1CC1CO1 ZFOWEXGOKLKOFQ-UHFFFAOYSA-N 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims description 2772
-1 cyanooxy Chemical group 0.000 claims description 1599
ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 claims description 270
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 222
239000002585 base Substances 0.000 claims description 156
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 117
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 105
125000000217 alkyl group Chemical group 0.000 claims description 93
239000007789 gas Substances 0.000 claims description 71
125000000623 heterocyclic group Chemical group 0.000 claims description 71
125000001424 substituent group Chemical group 0.000 claims description 54
238000000034 method Methods 0.000 claims description 44
238000006243 chemical reaction Methods 0.000 claims description 43
125000005842 heteroatom Chemical group 0.000 claims description 42
229910052736 halogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 40
150000002602 lanthanoids Chemical class 0.000 claims description 40
150000002923 oximes Chemical class 0.000 claims description 40
229910052747 lanthanoid Inorganic materials 0.000 claims description 39
125000003545 alkoxy group Chemical group 0.000 claims description 36
239000000126 substance Substances 0.000 claims description 36
125000001072 heteroaryl group Chemical group 0.000 claims description 35
229910052757 nitrogen Inorganic materials 0.000 claims description 34
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
229910052717 sulfur Inorganic materials 0.000 claims description 27
229920006395 saturated elastomer Polymers 0.000 claims description 26
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
125000004076 pyridyl group Chemical group 0.000 claims description 25
150000002431 hydrogen Chemical class 0.000 claims description 21
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 19
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
229910052707 ruthenium Inorganic materials 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 17
230000008569 process Effects 0.000 claims description 17
125000005843 halogen group Chemical group 0.000 claims description 16
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 15
125000001188 haloalkyl group Chemical group 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000002541 furyl group Chemical group 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
239000002689 soil Substances 0.000 claims description 12
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 11
125000003226 pyrazolyl group Chemical group 0.000 claims description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
241000233866 Fungi Species 0.000 claims description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000002971 oxazolyl group Chemical group 0.000 claims description 10
150000003573 thiols Chemical class 0.000 claims description 10
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims description 9
229940126543 compound 14 Drugs 0.000 claims description 9
239000000463 material Substances 0.000 claims description 9
150000001768 cations Chemical class 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000004438 haloalkoxy group Chemical group 0.000 claims description 8
125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 8
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
125000000232 haloalkynyl group Chemical group 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
229930192474 thiophene Natural products 0.000 claims description 7
125000001425 triazolyl group Chemical group 0.000 claims description 7
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical group CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
150000008052 alkyl sulfonates Chemical class 0.000 claims description 6
239000010949 copper Substances 0.000 claims description 6
125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
235000019253 formic acid Nutrition 0.000 claims description 6
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 6
JZSYSXZDIQUOGP-UHFFFAOYSA-N 2,4-difluoropyrimidine Chemical compound FC1=CC=NC(F)=N1 JZSYSXZDIQUOGP-UHFFFAOYSA-N 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 5
238000003776 cleavage reaction Methods 0.000 claims description 5
229910052802 copper Inorganic materials 0.000 claims description 5
125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
229910052742 iron Inorganic materials 0.000 claims description 5
229940098779 methanesulfonic acid Drugs 0.000 claims description 5
125000004269 oxiran-2-yl group Chemical group [H]C1([H])OC1([H])* 0.000 claims description 5
239000000843 powder Substances 0.000 claims description 5
230000007017 scission Effects 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
230000000739 chaotic effect Effects 0.000 claims description 4
125000001475 halogen functional group Chemical group 0.000 claims description 4
230000000749 insecticidal effect Effects 0.000 claims description 4
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
PENVYHXKYYCYML-UHFFFAOYSA-N 4-methoxypyrimidine Chemical group COC1=CC=NC=N1 PENVYHXKYYCYML-UHFFFAOYSA-N 0.000 claims description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
239000005864 Sulphur Substances 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
230000003032 phytopathogenic effect Effects 0.000 claims description 3
125000001725 pyrenyl group Chemical group 0.000 claims description 3
150000003852 triazoles Chemical class 0.000 claims description 3
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
YWMAPNNZOCSAPF-UHFFFAOYSA-N Nickel(1+) Chemical compound [Ni+] YWMAPNNZOCSAPF-UHFFFAOYSA-N 0.000 claims description 2
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
125000002723 alicyclic group Chemical group 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 2
125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
230000002538 fungal effect Effects 0.000 claims description 2
230000002147 killing effect Effects 0.000 claims description 2
229940006444 nickel cation Drugs 0.000 claims description 2
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
AVJLGPAUJVWLES-UHFFFAOYSA-N 2,4-dichloropurine Chemical compound C1=NC(Cl)=NC2(Cl)N=CN=C21 AVJLGPAUJVWLES-UHFFFAOYSA-N 0.000 claims 1
GLSHTINAZAWJBE-UHFFFAOYSA-N 2-chlorothiophene Chemical group ClC1=CC=[C]S1 GLSHTINAZAWJBE-UHFFFAOYSA-N 0.000 claims 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
BKBKTDKXZVCKEG-UHFFFAOYSA-N 4h-1,3,5-dioxazine Chemical compound C1OCN=CO1 BKBKTDKXZVCKEG-UHFFFAOYSA-N 0.000 claims 1
229930091051 Arenine Natural products 0.000 claims 1
229930006000 Sucrose Natural products 0.000 claims 1
125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000005109 alkynylthio group Chemical group 0.000 claims 1
230000000843 anti-fungal effect Effects 0.000 claims 1
229940121375 antifungal agent Drugs 0.000 claims 1
238000001354 calcination Methods 0.000 claims 1
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
125000003493 decenyl group Chemical group [H]C([*])=C([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])[H] 0.000 claims 1
238000009313 farming Methods 0.000 claims 1
230000002363 herbicidal effect Effects 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 claims 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-M o-toluate Chemical compound CC1=CC=CC=C1C([O-])=O ZWLPBLYKEWSWPD-UHFFFAOYSA-M 0.000 claims 1
125000000466 oxiranyl group Chemical group 0.000 claims 1
238000012856 packing Methods 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
239000005720 sucrose Substances 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
150000003536 tetrazoles Chemical class 0.000 claims 1
ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 299
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 268
241000196324 Embryophyta Species 0.000 description 32
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 26
229940125797 compound 12 Drugs 0.000 description 25
239000003053 toxin Substances 0.000 description 25
231100000765 toxin Toxicity 0.000 description 25
108700012359 toxins Proteins 0.000 description 25
239000000460 chlorine Substances 0.000 description 23
229910052731 fluorine Inorganic materials 0.000 description 20
239000002253 acid Substances 0.000 description 16
108090000623 proteins and genes Proteins 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
102000004169 proteins and genes Human genes 0.000 description 14
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 13
229910052799 carbon Inorganic materials 0.000 description 13
125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 13
235000018102 proteins Nutrition 0.000 description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 11
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 11
125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 11
125000004433 nitrogen atom Chemical group N* 0.000 description 11
239000011593 sulfur Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
240000008042 Zea mays Species 0.000 description 10
235000002017 Zea mays subsp mays Nutrition 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 10
125000004122 cyclic group Chemical group 0.000 description 10
239000011737 fluorine Substances 0.000 description 10
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 10
229920000742 Cotton Polymers 0.000 description 9
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
241000219146 Gossypium Species 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
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 description 9
229910052760 oxygen Inorganic materials 0.000 description 9
239000001301 oxygen Substances 0.000 description 9
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
125000003277 amino group Chemical group 0.000 description 8
125000004429 atom Chemical group 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
239000003112 inhibitor Substances 0.000 description 8
239000008267 milk Substances 0.000 description 8
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 8
125000000714 pyrimidinyl group Chemical group 0.000 description 8
MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical group FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
229940125782 compound 2 Drugs 0.000 description 7
235000013399 edible fruits Nutrition 0.000 description 7
230000000855 fungicidal effect Effects 0.000 description 7
238000010353 genetic engineering Methods 0.000 description 7
125000002883 imidazolyl group Chemical group 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
125000000842 isoxazolyl group Chemical group 0.000 description 7
235000013336 milk Nutrition 0.000 description 7
210000004080 milk Anatomy 0.000 description 7
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 7
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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
- 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
- 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
- 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
- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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TW097149852A 2007-12-19 2008-12-19 Azolylmethyloxiranes, their use and compositions comprising them TW200932116A (en)

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EP07123735		2007-12-19

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TW200932116A true TW200932116A (en)	2009-08-01

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TW097149852A TW200932116A (en)	2007-12-19	2008-12-19	Azolylmethyloxiranes, their use and compositions comprising them

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AR (1)	AR069835A1 (de)
CL (1)	CL2008003866A1 (de)
PE (1)	PE20091178A1 (de)
TW (1)	TW200932116A (de)
UY (1)	UY31563A1 (de)
WO (1)	WO2009077497A2 (de)

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CA2693997C (en)	2007-08-03	2013-01-15	Pierre L. Beaulieu	Viral polymerase inhibitors
CN101903351B (zh)	2007-12-19	2014-09-10	贝林格尔.英格海姆国际有限公司	病毒聚合酶抑制剂
WO2011069894A1 (de)	2009-12-08	2011-06-16	Basf Se	Triazolverbindungen, ihre verwendung sowie sie enthaltende mittel
WO2011069916A1 (de)	2009-12-08	2011-06-16	Basf Se	Triazolverbindungen, ihre verwendung als fungizide sowie sie enthaltende mittel
EP2513067A1 (de)	2009-12-18	2012-10-24	Basf Se	Verfahren zur herstellung von triazolinthionderivaten und zwischenprodukten daraus
MX2012009805A (es)	2010-03-16	2012-09-12	Basf Se	Un proceso usando reactivos de grignard.
EP2621922A1 (de)	2010-09-30	2013-08-07	Basf Se	Verfahren für die synthese von thiotriazolgruppen enthaltenden verbindungen
WO2012130823A1 (en)	2011-03-30	2012-10-04	Basf Se	Suspension concentrates
WO2012146598A1 (en)	2011-04-28	2012-11-01	Basf Se	Process for the preparation of 2-substituted 4-amino-2,4-dihydro-[1,2,4]triazole-3-thiones
WO2012146535A1 (en)	2011-04-28	2012-11-01	Basf Se	Process for the preparation of 2-substituted 2,4-dihydro-[1,2,4]triazole-3-thiones
EP2746264A1 (de)	2012-12-19	2014-06-25	Basf Se	Substituierte [1,2,4]-Triazol- und Imidazolverbindungen
EP2746277A1 (de)	2012-12-19	2014-06-25	Basf Se	Fungizidimidazolyl- und -triazolylverbindungen
EP2746255A1 (de)	2012-12-19	2014-06-25	Basf Se	Substituierte [1,2,4]-Triazol- und Imidazolverbindungen
EP2746256A1 (de)	2012-12-19	2014-06-25	Basf Se	Fungizidimidazolyl- und -triazolylverbindungen
WO2014095249A1 (en)	2012-12-19	2014-06-26	Basf Se	Fungicidal imidazolyl and triazolyl compounds
WO2014095381A1 (en)	2012-12-19	2014-06-26	Basf Se	Fungicidal imidazolyl and triazolyl compounds
EP2746279A1 (de)	2012-12-19	2014-06-25	Basf Se	Fungizidimidazolyl- und -triazolylverbindungen
EP2746258A1 (de)	2012-12-21	2014-06-25	Basf Se	Substituierte [1,2,4]Triazol- und Imidazolverbindungen
EP2746259A1 (de)	2012-12-21	2014-06-25	Basf Se	Substituierte [1,2,4]Triazol- und Imidazolverbindungen
EP2746257A1 (de)	2012-12-21	2014-06-25	Basf Se	Substituierte [1,2,4]Triazol- und Imidazolverbindungen
EP2746260A1 (de)	2012-12-21	2014-06-25	Basf Se	Substituierte [1,2,4]Triazol- und Imidazolverbindungen
CA3038401A1 (en) *	2016-09-29	2018-04-05	Bayer Cropscience Aktiengesellschaft	5-substituted imidazolylmethyloxirane derivatives as fungicides

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DE3805684A1 (de) *	1988-02-24	1989-09-07	Basf Ag	Azolylmethylcycloalkyloxirane, ihre herstellung und verwendung als pflanzenschutzmittel
IL95493A0 (en) *	1989-09-09	1991-06-30	Basf Ag	Azolylmethyloxiranes,their manufacture and their use as fungicides
DE19520097A1 (de) *	1995-06-01	1996-12-05	Bayer Ag	Triazolylmethyl-oxirane
DE19617461A1 (de) *	1996-05-02	1997-11-06	Bayer Ag	Acylmercapto-triazolyl-Derivate
EP1030847B1 (de) *	1997-10-08	2006-03-22	Bayer CropScience AG	Verfahren zur herstellung von triazolinthion-derivaten
DE19744401A1 (de) *	1997-10-08	1999-04-15	Bayer Ag	Verfahren zur Herstellung von Triazolinthion-Derivaten
DE19744400A1 (de) *	1997-10-08	1999-04-15	Bayer Ag	Verfahren zur Herstellung von Triazolinthion-Derivaten
US7910614B2 (en) *	2006-07-25	2011-03-22	Basf Se	Azolylmethyloxiranes, use thereof for controlling plant pathogenic fungi, and agents containing the same

2008
- 2008-12-15 WO PCT/EP2008/067539 patent/WO2009077497A2/de not_active Ceased
- 2008-12-18 AR ARP080105548A patent/AR069835A1/es not_active Application Discontinuation
- 2008-12-19 UY UY31563A patent/UY31563A1/es unknown
- 2008-12-19 TW TW097149852A patent/TW200932116A/zh unknown
- 2008-12-19 PE PE2008002153A patent/PE20091178A1/es not_active Application Discontinuation
- 2008-12-19 CL CL2008003866A patent/CL2008003866A1/es unknown

Also Published As

Publication number	Publication date
CL2008003866A1 (es)	2009-11-27
WO2009077497A2 (de)	2009-06-25
PE20091178A1 (es)	2009-09-03
UY31563A1 (es)	2009-07-17
AR069835A1 (es)	2010-02-24
WO2009077497A3 (de)	2010-01-28

Publication	Publication Date	Title
TW200932116A (en)	2009-08-01	Azolylmethyloxiranes, their use and compositions comprising them
US20100273651A1 (en)	2010-10-28	Azolylmethyloxiranes, use Thereof and Agents Containing the Same
TW200930299A (en)	2009-07-16	Azolylmethyloxiranes, their use and compositions comprising them
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US11425910B2 (en)	2022-08-30	Substituted oxadiazoles for combating phytopathogenic fungi
TW201103920A (en)	2011-02-01	Triazole compounds carrying a sulfur substituent X
TW200932117A (en)	2009-08-01	Azolylmethyloxiranes, their use and compositions comprising them
US20180354920A1 (en)	2018-12-13	Substituted oxadiazoles for combating phytopathogenic fungi
WO2017148797A1 (en)	2017-09-08	Substituted oxadiazoles for combating phytopathogenic fungi
TW201103430A (en)	2011-02-01	Triazole compounds carrying a sulfur substituent XII
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TW201018406A (en)	2010-05-16	Triazole and imidazole compounds, their use and compositions comprising them
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