AU2009262515A1 - Thiadiazolyloxyphenylamidines and use thereof as fungicides - Google Patents

Info

Publication number

AU2009262515A1

AU2009262515A1 AU2009262515A AU2009262515A AU2009262515A1 AU 2009262515 A1 AU2009262515 A1 AU 2009262515A1 AU 2009262515 A AU2009262515 A AU 2009262515A AU 2009262515 A AU2009262515 A AU 2009262515A AU 2009262515 A1 AU2009262515 A1 AU 2009262515A1

Authority

AU

Australia

Prior art keywords

thiadiazol

oxy

groups

chosen

formula

Prior art date

2008-06-27

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 239000000417 fungicide Substances 0.000 title description 9
• -1 pyrrolidyl Chemical group 0.000 claims description 157
• 239000000203 mixture Substances 0.000 claims description 84
• 238000006243 chemical reaction Methods 0.000 claims description 60
• 125000004122 cyclic group Chemical group 0.000 claims description 55
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 39
• 229910052698 phosphorus Inorganic materials 0.000 claims description 38
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 34
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 125000005842 heteroatom Chemical group 0.000 claims description 33
• 238000000034 method Methods 0.000 claims description 33
• 150000001408 amides Chemical class 0.000 claims description 29
• 244000005700 microbiome Species 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 229940039407 aniline Drugs 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 150000001409 amidines Chemical class 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 125000004429 atom Chemical group 0.000 claims description 18
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• 150000003568 thioethers Chemical class 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 230000008569 process Effects 0.000 claims description 11
• 239000000460 chlorine Substances 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 9
• 230000009467 reduction Effects 0.000 claims description 8
• 125000002723 alicyclic group Chemical group 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• PAGDTTPJSICKIZ-UHFFFAOYSA-N n'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-n-ethyl-n-methylmethanimidamide Chemical compound C1=C(C)C(N=CN(C)CC)=CC(C)=C1OC1=NC(CC=2C=CC(Cl)=CC=2)=NS1 PAGDTTPJSICKIZ-UHFFFAOYSA-N 0.000 claims description 7
• 150000002905 orthoesters Chemical class 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• FQDKWMRPEZAPPS-UHFFFAOYSA-N n'-[2,5-dimethyl-4-[[3-(1-phenylethyl)-1,2,4-thiadiazol-5-yl]oxy]phenyl]-n-ethyl-n-methylmethanimidamide Chemical compound C1=C(C)C(N=CN(C)CC)=CC(C)=C1OC1=NC(C(C)C=2C=CC=CC=2)=NS1 FQDKWMRPEZAPPS-UHFFFAOYSA-N 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
• NDAJNMAAXXIADY-UHFFFAOYSA-N 2-methylpropanimidamide Chemical compound CC(C)C(N)=N NDAJNMAAXXIADY-UHFFFAOYSA-N 0.000 claims description 4
• 150000001721 carbon Chemical group 0.000 claims description 4
• IGZHVMCTSXDDLE-UHFFFAOYSA-N n'-[4-[[3-(1,3-benzodioxol-5-ylmethyl)-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-n-ethyl-n-methylmethanimidamide Chemical compound C1=C(C)C(N=CN(C)CC)=CC(C)=C1OC1=NC(CC=2C=C3OCOC3=CC=2)=NS1 IGZHVMCTSXDDLE-UHFFFAOYSA-N 0.000 claims description 4
• KVFRUNNUFDAOJD-UHFFFAOYSA-N n-[2,5-dimethyl-4-[[3-(1-phenylethyl)-1,2,4-thiadiazol-5-yl]oxy]phenyl]-1-piperidin-1-ylmethanimine Chemical compound C=1C=CC=CC=1C(C)C(N=1)=NSC=1OC(C(=C1)C)=CC(C)=C1N=CN1CCCCC1 KVFRUNNUFDAOJD-UHFFFAOYSA-N 0.000 claims description 4
• KFYOELSYSKKLSU-UHFFFAOYSA-N n-[4-[[3-(1,3-benzodioxol-5-ylmethyl)-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-1-piperidin-1-ylmethanimine Chemical compound CC=1C=C(OC=2SN=C(CC=3C=C4OCOC4=CC=3)N=2)C(C)=CC=1N=CN1CCCCC1 KFYOELSYSKKLSU-UHFFFAOYSA-N 0.000 claims description 4
• RHCNVKUEPUWRDD-UHFFFAOYSA-N n-[4-[[3-[1-(4-chlorophenyl)ethyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-1-piperidin-1-ylmethanimine Chemical compound C=1C=C(Cl)C=CC=1C(C)C(N=1)=NSC=1OC(C(=C1)C)=CC(C)=C1N=CN1CCCCC1 RHCNVKUEPUWRDD-UHFFFAOYSA-N 0.000 claims description 4
• OQCFVYCEOOKGRR-UHFFFAOYSA-N n-ethyl-n'-[4-[[3-[(3-methoxyphenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-n-methylmethanimidamide Chemical compound C1=C(C)C(N=CN(C)CC)=CC(C)=C1OC1=NC(CC=2C=C(OC)C=CC=2)=NS1 OQCFVYCEOOKGRR-UHFFFAOYSA-N 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 150000005181 nitrobenzenes Chemical class 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000003944 tolyl group Chemical group 0.000 claims description 3
• 150000001448 anilines Chemical class 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 125000005936 piperidyl group Chemical group 0.000 claims description 2
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
• DSEHWDFPVDXKQM-UHFFFAOYSA-N n'-propan-2-ylethanimidamide Chemical compound CC(C)N=C(C)N DSEHWDFPVDXKQM-UHFFFAOYSA-N 0.000 claims 4
• HWHKANWHVGKGPE-UHFFFAOYSA-N n'-[5-chloro-4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2-methylphenyl]-n-ethyl-n-methylmethanimidamide Chemical compound C1=C(C)C(N=CN(C)CC)=CC(Cl)=C1OC1=NC(CC=2C=CC(Cl)=CC=2)=NS1 HWHKANWHVGKGPE-UHFFFAOYSA-N 0.000 claims 3
• NVFPHKSEIQNWCE-UHFFFAOYSA-N n'-methylmethanimidamide Chemical compound CNC=N NVFPHKSEIQNWCE-UHFFFAOYSA-N 0.000 claims 3
• PCIRKQJSFXEVJL-UHFFFAOYSA-N n'-[4-[[3-[(2,4-dichlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-n-ethyl-n-methylmethanimidamide Chemical compound C1=C(C)C(N=CN(C)CC)=CC(C)=C1OC1=NC(CC=2C(=CC(Cl)=CC=2)Cl)=NS1 PCIRKQJSFXEVJL-UHFFFAOYSA-N 0.000 claims 2
• AJAXLSIVUHAZSG-UHFFFAOYSA-N n'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-n-methyl-n-propan-2-ylmethanimidamide Chemical compound C1=C(C)C(N=CN(C)C(C)C)=CC(C)=C1OC1=NC(CC=2C=CC(Cl)=CC=2)=NS1 AJAXLSIVUHAZSG-UHFFFAOYSA-N 0.000 claims 2
• HWTWABXTTINVFD-UHFFFAOYSA-N n'-[4-[[3-[(5-bromo-2-methylphenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-n-ethyl-n-methylmethanimidamide Chemical compound C1=C(C)C(N=CN(C)CC)=CC(C)=C1OC1=NC(CC=2C(=CC=C(Br)C=2)C)=NS1 HWTWABXTTINVFD-UHFFFAOYSA-N 0.000 claims 2
• SVKQJKDFMLYPSM-UHFFFAOYSA-N n'-methylpropanimidamide Chemical compound CCC(=N)NC SVKQJKDFMLYPSM-UHFFFAOYSA-N 0.000 claims 2
• BAIKAQYJTSWANU-UHFFFAOYSA-N n-[2,5-dimethyl-4-[[3-[[2-(trifluoromethyl)phenyl]methyl]-1,2,4-thiadiazol-5-yl]oxy]phenyl]-1-piperidin-1-ylmethanimine Chemical compound CC=1C=C(OC=2SN=C(CC=3C(=CC=CC=3)C(F)(F)F)N=2)C(C)=CC=1N=CN1CCCCC1 BAIKAQYJTSWANU-UHFFFAOYSA-N 0.000 claims 2
• KIUVTIAJWSNNNB-UHFFFAOYSA-N n-[4-[[3-[(2-methoxyphenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-1-piperidin-1-ylmethanimine Chemical compound COC1=CC=CC=C1CC1=NSC(OC=2C(=CC(=C(C)C=2)N=CN2CCCCC2)C)=N1 KIUVTIAJWSNNNB-UHFFFAOYSA-N 0.000 claims 2
• GKGITXVNGMIYID-UHFFFAOYSA-N n-[4-[[3-[(3,4-dichlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-1-piperidin-1-ylmethanimine Chemical compound CC=1C=C(OC=2SN=C(CC=3C=C(Cl)C(Cl)=CC=3)N=2)C(C)=CC=1N=CN1CCCCC1 GKGITXVNGMIYID-UHFFFAOYSA-N 0.000 claims 2
• OJDPXZIQWABLBZ-UHFFFAOYSA-N n-[4-[[3-[(4-bromophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-1-piperidin-1-ylmethanimine Chemical compound CC=1C=C(OC=2SN=C(CC=3C=CC(Br)=CC=3)N=2)C(C)=CC=1N=CN1CCCCC1 OJDPXZIQWABLBZ-UHFFFAOYSA-N 0.000 claims 2
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• OIJLYXDENHSVPU-UHFFFAOYSA-N n-phenyl-1-piperidin-1-ylmethanimine Chemical compound C1CCCCN1C=NC1=CC=CC=C1 OIJLYXDENHSVPU-UHFFFAOYSA-N 0.000 claims 2
• HEDRJSWPTSCHKP-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)peroxybenzene Chemical class [O-][N+](=O)C1=CC=CC=C1OOOC1=CC=CC=C1[N+]([O-])=O HEDRJSWPTSCHKP-UHFFFAOYSA-N 0.000 claims 1
• CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 claims 1
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