AU664780B2 - Substituted triazolinones - Google Patents

Substituted triazolinones Download PDF

Info

Publication number: AU664780B2
Authority: AU; Australia
Prior art keywords: carbon atoms; case; chain; straight; branched
Prior art date: 1992-10-12
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.): Expired - Fee Related

Application number

AU51106/93A

Other languages

English (en)

Other versions

AU5110693A (en

Inventor

Kurt Findeisen

Klaus Konig

Karl-Heinz Linker

Klaus-Helmut Muller

Hans-Joachim Santel

Otto Schallner

Robert R Schmidt

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

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.)

1992-10-12

Filing date

1993-10-04

Publication date

1995-11-30

1993-10-04 Application filed by Bayer AG filed Critical Bayer AG

1994-05-09 Publication of AU5110693A publication Critical patent/AU5110693A/en

1995-11-30 Application granted granted Critical

1995-11-30 Publication of AU664780B2 publication Critical patent/AU664780B2/en

2013-10-04 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

125000004432 carbon atom Chemical group C* 0.000 claims description 307
125000000217 alkyl group Chemical group 0.000 claims description 188
125000001424 substituent group Chemical group 0.000 claims description 136
-1 cyano, amino Chemical group 0.000 claims description 99
125000003545 alkoxy group Chemical group 0.000 claims description 81
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 66
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 66
229910052794 bromium Inorganic materials 0.000 claims description 66
239000000460 chlorine Substances 0.000 claims description 66
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 65
229910052801 chlorine Inorganic materials 0.000 claims description 65
229910052731 fluorine Inorganic materials 0.000 claims description 62
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 61
239000011737 fluorine Substances 0.000 claims description 61
125000003342 alkenyl group Chemical group 0.000 claims description 50
125000006193 alkinyl group Chemical group 0.000 claims description 48
125000003118 aryl group Chemical group 0.000 claims description 48
125000000753 cycloalkyl group Chemical group 0.000 claims description 48
125000004414 alkyl thio group Chemical group 0.000 claims description 45
229910052736 halogen Inorganic materials 0.000 claims description 45
150000002367 halogens Chemical class 0.000 claims description 45
125000005843 halogen group Chemical group 0.000 claims description 41
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 39
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 38
239000005864 Sulphur Chemical group 0.000 claims description 38
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
229910052757 nitrogen Inorganic materials 0.000 claims description 38
229910052760 oxygen Inorganic materials 0.000 claims description 38
239000001301 oxygen Substances 0.000 claims description 38
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
125000004093 cyano group Chemical group *C#N 0.000 claims description 33
125000001188 haloalkyl group Chemical group 0.000 claims description 33
125000000623 heterocyclic group Chemical group 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 30
238000000034 method Methods 0.000 claims description 30
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
150000002431 hydrogen Chemical class 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000004438 haloalkoxy group Chemical group 0.000 claims description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
125000003710 aryl alkyl group Chemical group 0.000 claims description 18
125000004104 aryloxy group Chemical group 0.000 claims description 18
125000005842 heteroatom Chemical group 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 16
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229920006395 saturated elastomer Polymers 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
125000003884 phenylalkyl group Chemical group 0.000 claims description 11
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 10
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
125000000547 substituted alkyl group Chemical group 0.000 claims description 8
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
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239000002689 soil Substances 0.000 claims description 5
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125000003107 substituted aryl group Chemical group 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
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239000013543 active substance Substances 0.000 claims 1
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239000008187 granular material Substances 0.000 description 6
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239000000126 substance Substances 0.000 description 6
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
241000209510 Liliopsida Species 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
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238000005160 1H NMR spectroscopy Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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125000001309 chloro group Chemical group Cl* 0.000 description 2
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GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 1
QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 description 1
239000006260 foam Substances 0.000 description 1
BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
229940097068 glyphosate Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
QTXRJCHTPLNKKZ-UHFFFAOYSA-N isocyanatomethyl(trimethyl)silane Chemical compound C[Si](C)(C)CN=C=O QTXRJCHTPLNKKZ-UHFFFAOYSA-N 0.000 description 1
PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 1
CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000004579 marble Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
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MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
WXUNXXKSYBUHMK-UHFFFAOYSA-N methyl 4-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate;methyl 5-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical compound COC(=O)C1=CC=C(C)C=C1C1=NC(C)(C(C)C)C(=O)N1.COC(=O)C1=CC(C)=CC=C1C1=NC(C)(C(C)C)C(=O)N1 WXUNXXKSYBUHMK-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
229940042880 natural phospholipid Drugs 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000011368 organic material Substances 0.000 description 1
UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229960004109 potassium acetate Drugs 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
229960003351 prussian blue Drugs 0.000 description 1
239000013225 prussian blue Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011435 rock Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229960004249 sodium acetate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

AU51106/93A 1992-10-12 1993-10-04 Substituted triazolinones Expired - Fee Related AU664780B2 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE4234306		1992-10-12
DE4234306A DE4234306A1 (de)	1992-10-12	1992-10-12	Substituierte Triazolinone
PCT/EP1993/002705 WO1994009012A1 (de)	1992-10-12	1993-10-04	Substituierte triazolinone

Publications (2)

Publication Number	Publication Date
AU5110693A AU5110693A (en)	1994-05-09
AU664780B2 true AU664780B2 (en)	1995-11-30

Family

ID=6470232

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU51106/93A Expired - Fee Related AU664780B2 (en)	1992-10-12	1993-10-04	Substituted triazolinones

Country Status (8)

Country	Link
EP (1)	EP0663917A1 (de)
JP (1)	JPH08505837A (de)
AU (1)	AU664780B2 (de)
BR (1)	BR9307225A (de)
CA (1)	CA2146661A1 (de)
DE (1)	DE4234306A1 (de)
RU (1)	RU95113591A (de)
WO (1)	WO1994009012A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP6071780B2 (ja) *	2013-07-02	2017-02-01	四国化成工業株式会社	アゾールシラン化合物、該化合物の合成方法及びその利用
JP6071806B2 (ja) *	2013-08-27	2017-02-01	四国化成工業株式会社	アゾールシラン化合物、該化合物の合成方法及びその利用
EP3018137B1 (de) *	2013-07-02	2018-10-17	Shikoku Chemicals Corporation	Azolsilanverbindung, oberflächenbehandlungslösung, oberflächenbehandlungsverfahren und verwendung davon

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3723246A1 (de) *	1987-07-14	1989-01-26	Lentia Gmbh	Neue thienyl-azolylmethyl-silane
DE4109671A1 (de) *	1991-03-23	1992-09-24	Bayer Ag	Substituierte triazolinone
JP2823614B2 (ja) *	1989-12-15	1998-11-11	株式会社日立製作所	階調表示方式および液晶表示装置

1992
- 1992-10-12 DE DE4234306A patent/DE4234306A1/de not_active Withdrawn
1993
- 1993-10-04 BR BR9307225A patent/BR9307225A/pt not_active Application Discontinuation
- 1993-10-04 CA CA002146661A patent/CA2146661A1/en not_active Abandoned
- 1993-10-04 AU AU51106/93A patent/AU664780B2/en not_active Expired - Fee Related
- 1993-10-04 EP EP93921909A patent/EP0663917A1/de not_active Ceased
- 1993-10-04 JP JP6509576A patent/JPH08505837A/ja active Pending
- 1993-10-04 WO PCT/EP1993/002705 patent/WO1994009012A1/de not_active Application Discontinuation
- 1993-10-04 RU RU95113591/04A patent/RU95113591A/ru unknown

Also Published As

Publication number	Publication date
EP0663917A1 (de)	1995-07-26
WO1994009012A1 (de)	1994-04-28
RU95113591A (ru)	1996-12-27
CA2146661A1 (en)	1994-04-28
JPH08505837A (ja)	1996-06-25
AU5110693A (en)	1994-05-09
DE4234306A1 (de)	1994-04-14
BR9307225A (pt)	1999-05-11

Publication	Publication Date	Title
EP0609734B1 (de)	1997-08-27	Substituierte Triazolinone sowie ihre Verwendung als Herbizide
AU697764B2 (en)	1998-10-15	N-cyanoaryl nitrogen heterocycles
CA2226669C (en)	2006-10-17	Herbicidal sulphonylamino(thio)carbonyl compounds
EP0610733A1 (de)	1994-08-17	1-Aryltriazolin(thi)one
US5021080A (en)	1991-06-04	Herbicidal substituted 4-amino-5-alkylthio-1,2,4-triazol-3-ones
AU672000B2 (en)	1996-09-19	Heterocyclyltriazolinones
US6121204A (en)	2000-09-19	Herbicidal or fungicidal sulphonylaminocarbonyltriazolinones with halogenated alk(en)oxy substituents
EP0558999A2 (de)	1993-09-08	N-Aryl-Pyrazolderivative als Herbizide
US5994273A (en)	1999-11-30	Herbicidal or fungicidal sulphonylaminocarbonyltriazolinones with halogenated alk(en)ylthio substituents
EP0885200B1 (de)	2008-05-21	Substituierte arylsulfonyl(thio)harnstoffe als herbizide
US4988380A (en)	1991-01-29	Use of difluoromethyl-thiadiazolyl-oxyacetamides as selective herbicides
CA2256332C (en)	2005-12-27	Substituted sulphonyl amino(thio)carbonyl compounds and their use as herbicides
US5496793A (en)	1996-03-05	Substituted carbamoyltriazoles
EP0648772B1 (de)	2002-09-04	4-Cyanophenyliminoheterocyclen
AU664780B2 (en)	1995-11-30	Substituted triazolinones
AU672204B2 (en)	1996-09-26	Heterocyclyltriazolinones
US5328897A (en)	1994-07-12	Herbicidal 2-(2-benzoxazolyl-oxy)-acetamides
DE4219246A1 (de)	1993-12-16	Neue 2-(7-Chlor-2-benzoxazolyloxy)-acetamide
US5525579A (en)	1996-06-11	Substituted triazolinones
AU655019B2 (en)	1994-12-01	2-amido-1,2,4-triazolinone derivatives
CA2248290A1 (en)	1997-09-12	Substituted thienyl sulphonyl (thio) ureas as herbicides
US5332719A (en)	1994-07-26	Substituted triazolinones
US5183932A (en)	1993-02-02	Herbicidal substituted 4-amino-5-alkylthio-1,2,4-triazol-3-ones
CA2201596A1 (en)	1996-04-18	Sulfonylaminocarbonyltriazolinones with substituents bound by oxygen and sulphur
CA2214752C (en)	2006-10-24	Herbicidal or fungicidal sulphonylaminocarbonyltriazolinones with halogenated alk(en)oxy substituents