AU664780B2 - Substituted triazolinones - Google Patents
Substituted triazolinones Download PDFInfo
- Publication number
- AU664780B2 AU664780B2 AU51106/93A AU5110693A AU664780B2 AU 664780 B2 AU664780 B2 AU 664780B2 AU 51106/93 A AU51106/93 A AU 51106/93A AU 5110693 A AU5110693 A AU 5110693A AU 664780 B2 AU664780 B2 AU 664780B2
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- Australia
- Prior art keywords
- carbon atoms
- case
- chain
- straight
- branched
- Prior art date
- 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.)
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- 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
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- 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
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
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- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
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- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-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
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- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- WZJZMXBKUWKXTQ-UHFFFAOYSA-N desmedipham Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=CC=CC=2)=C1 WZJZMXBKUWKXTQ-UHFFFAOYSA-N 0.000 description 1
- 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
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
OPI DATE 09/05/94 APPLN. ID 51106/93 AOJP QATE,,21/07/94 PCT NUMBER PCT/EP93/02705 AU9351 106 (51) Internationale Patentkilassifkation 5 Internationale Vcr6ffentlichungsnummer: WNO 94/09012 C07F 7/08, 7/18, AO1N 55/00 Al (43) Internationales Ver6ffentlichungsdatumn: 28. April 1994 (28.04.94) (21) Interuationales Aktenzeichen: PCT/EP93/02705 (81) Bcstimmungsstaaten: AU, BR, BY, CA, CZ, RU, JP, KR, KZ, NZ, RU, SK, UA, US, europflisches Patent (AT, (22) IAnternationales Anmeldedatuin: 4. Oktober 1993 (04.10.93) BE, CR, DE, DK, ES, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE).
Priori tftsdaten: P 42 34 306.2 12. Oktober 1992 (12.10.92) DE Veriiffentlicht Alit internationalem Recherchenbericlil.
(71) Anmelder (Iir alle Bestdmrn ngsstaazen ausser US): BAYE k n pi AKTI ENGESELLSCHAFT [DE/DE]; D-5 1368 Leverkusen (DE), (72) Erfinder; und Erlinder/Anmelder (nurfiir US) FINDEISEN, Kurt [DE/ DE]; Dfinfelder Strasse 28, D-5 1375 Leverkusen (DE).
LINKER, Karl-Heinz [DE/DE]; Albert-Schweizer- Strasse 3, D-51377 Leverkusen SCHALLNER, Otto Noldeweg 22, D-40789 Monheim (DE).
MULLER, Klaus-Relmut [AT/DE]; Solfstrasse 55, D- 40593 D~sseldorf KONIG, Klaus [DE/DE]; Zum, Hahnberg 40, D-51519 Odenthal SANTEL, Hans- Joachim [DE/DE]; GOfnstrasse 9a, D-51371 Leverkusen SCRMIDT, Robert, R. [DE/DE]; Im Waidwinkel 110, D-5 1467 Bergisch-Gladbach (DE).
(54) Title: SUBSTITUTED TRIAZOLINONES (54) Bezeichnung: S UBSTITUIERTE TRIAZOLINONE IRt
R
1~ 2 X '-NHA-Si-R 13
R
R R!
I
"'N
R!
(57) Abstract The invention relates to novel substituted triazolinones of general formula where Ret is a heterocycle of formula or and R 1
R
2
R
3 A, X 1
R
4
R
5
R
6
R
7 and X2 have the meanings given in the description, several processes for their production and their use as herbicides.
(57) Zusamnmenfassung Die Erfindung betrifft neue substituierte Triazolinone der allgemneinen Formel in der Het for einen Reterocyclus der Format, oder staht, und R1, R0 2
R
3 A, X I, R 4
R
5
R
6
R
7 und X2 die in der Beschreibung angegebenen Bedeutungen haben, mebrere Verfahren zu ibrer Herstellung und ihre Verwendung als Rerbizide.
4Ie BAYER AKIENGESELLSCHAFT Konzemverwaltung RP Patente Konzem 51368 Leverkusen Substituted triazolinones The invention relates to novel substituted triazolinones, to a number of processes for their preparation and to their use as herbicides.
It is known that certain substituted triazolinones, such as, for example, the compound 2-methyl-3- dimethylamino- 1- [N-(2,2-dimethyl- 1-propyl)aminocarbonyl]- 1,2,4-triazolin-5-one, possess herbicidal properties (cf. e.g. EP 431 390).
However, the herbicidal activity of these previously known compounds with respect to problem weeds, and their tolerance by important crop plants, is not completely satisfactory in all areas of application.
Novel substituted triazolinones have been found of the general formula (I) I 2 1 X ',8 in which Het represents a heterocycle of the formula Le A 29 399-PCT R R R I I
R
1
R
2 and R 3 independently of one another each represent halogen, alkyl, alkenyl, alkinyl or alkoxy or represent in each case optionally substituted arylalkyl, aryl or aryloxy, A represents a divalent alkanediyl radical, and X' represents oxygen or sulphur, where
R
4 represents hydrogen, halogen, cyano or nitro or represents optionally substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl, halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, or represents a radical of the formula
R
R
5 represents hydrogen or cyano, or represents optionally substituted alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or aminocarbonyl, or represents amino, N-alkylamino, N,Ndialkylamino or alkylideneimino, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy,
R
6 represents alkyl, alkoxy or alkylthio, or represents a radical of the Le A29 399-PCT -2-
R
formula _1
R
7 represents alkyl or cycloalkyl,
R
8 and R 9 either independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case optionally substituted arylalkyl or aryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, R1 0 and R" either independently of one another each represent alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each case optionally substituted aryl, arylalkyl or heteroaryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, and
X
2 represents oxygen or sulphur.
The compounds of the formula-(I) may if appropriate, depending on the nature of the substituents, be present as geometrical and/or optical isomers or isomer mixtures of different composition. Both the pure isomers and the isomer mixtures are claimed according to the invention.
It has furthermore been found that the novel substituted triazolinones of the general formula (I)
R
I R X -A-Si-R
(I)
13
R
Le A 29 399 -3in which Het represents a heterocycle of the foimula R R! R! or Rp7 I
I
R
2 and R 3 independently of one another each represent halogen, alkyl, alkenyl, alkinyl or alkoxy or represent in each case optionally substituted arylalkyl, aryl or aryloxy, A represents a divalent alkanediyl radical, and X' represents oxygen or sulphur, where
R
4 represents hydrogen, halogen, cyano or nitro or represents optionally substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl, halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, or represents a radical of the formula 'R9
R
5 represents hydrogen or cyano, or represents optionally substituted alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or aminocarbonyl, or represents amino, N-alkylamino, N,Ndialkylamino or alkylideneimino, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, Le A 29 399 -4-
R
6 represents alkyl, alkoxy or alkylthio, or represents a radical of the
RE
formula
R
7 represents alkyl or cycloalkyl,
R
8 and R 9 either independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case optionally substituted arylalkyl or aryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle,
R
1 and R" either independently of one another each represent alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each case optionally substituted aryl, arylalkyl or heteroaryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, and
X
2 represents oxygen or sulphur, are obtained if a) 1-chloro(thio)carbonyltriazolinones of the formula (II) xL.C.C (II) in which Het and X' have the meanings given above Le A 29 399 are reacted with amines of the formula (III)
R
I 2 )N-A-Si--R m) in which R R 2
R
3 and A have the meanings given above, optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary, or if b) 1-unsubstituted triazolinones of the formula (IV) Het-H (IV) in which Het has the meaning given above are reacted with iso(thio)cyanates of the formula (V)
R
X=C=N-A-Si-R
(V)
13
R
in which
R
2
R
3 A and X' have the meanings given above, optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary.
-6- Finally it has been found that the novel substituted triazolinones of the general formula possess herbicidal properties.
SSurprisingly, the substituted triazolinones according to the aivention, of the general formula display a considerably improved herbicidal activity with respect to problem weeds, while at the same time being tolerated to a markedly increased extent by important crop plants, in comparison with the substituted triazolinones known from the prior art, such as, for example, the compound 2methyl-3- dimethylamino- 1- dimethyl- 1-propyl)- aminocarbonyl]- 1,2,4which compounds are closely related chemically and in terms of their mode of action.
A general definition of the substituted triazolinones according to the invention is given by the formula Preferred compounds of the formula are those in which Het represents a heterocycle of the formula 1N 6 R' R R N X or N I I
R
2 and R 3 independently of one another each represent fluorine, chlorine, bromine or iodine, or represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 8 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 8 carbon atoms, or represent straight-chain or branched alkoxy having 1 to 8 carbon atoms, or represent arylalkyl, aryl or aryloxy having in each case 6 to 10 carbon atoms in the aryl moiety and appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or Le A 29 399 7polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 co 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight- chain or branched alkyl having 1 to 6 carbon atoms, A represents a divalent alkanediyl radical having 1 to 8 carbon atoms, and X' represents oxygen or sulphur, where
R
4 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano or nitro, or represents straight-chain or branched alkyl 4which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,Ndialkylamino having in each case 1 to 8 carbon atoms in the individual alkyl moieties;
R
4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, in particular fluorine, chlorine, bromine and/or iodine, Le A 29 399 8- I or represents in each case straight-chain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 8 carbon atoms in the individual alkyl moieties, or moreover represents cycloalkyl having 3 to 8 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, or furthermore represents aryl or aryloxy having in each case 6 to 10 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms,
R'
or R represents a radical of the formula _W, \R9
R
5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 8 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case Le A 29 399 -9straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,Ndialkylamino having in each case 1 to 8 carbon atoms in the individual alkyl moieties;
R
5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N,N-dialkylamino or alkylideneimino having in each case 1 to 8 carbon atoms in the individual alkyl moieties, oc furthermore represents cycloalkyl having 3 to 8 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, or furthermore represents aryl or aryloxy having in each case 6 to 10 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substitucnts, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms,
R
6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 8 carbon atoms, or represents a radical
R
of the formula _h y, Le A 29 399
R
7 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or represents cycloalkyl having 3 to 8 carbon atoms,
R
8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or each represent straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represent cycloalkyl having 3 to 8 carbon atoms, or represent arylalkyl or aryl having in each case 6 to carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 to 2 further heteroatoms in particular nitrogen, oxygen or sulphur and which is optionally monosubstituted or rolysubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 4 carbon atoms,
R
1 and R" either independently of one another each represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or represent in each case 11 I ~1 I straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, especially fluorine, chlorine, bromine and/or iodine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, especially fluorine, chlorine, bromine and/or iodine, or represent in each case straight-chain or branched alkoxyalkyl or alkoxy having in each case 1 to 8 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 8 carbon atoms, or represent cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, or represent aryl or arylalkyl having in each case 6 to 10 carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, or represent heteroaryl having 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl and heteroaryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms; Le A 29 399 12or R' 0 and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 to 2 further heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 4 carbon atoms, and
X
2 represents oxygen or sulphur.
Particularly preferred compounds of the formula are those in which Het represents a heterocycle of the formula
R
4
R
6 or R
R
2 and R 3 independently of one another each represent fluorine, chlorine or bromine, or represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 6 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 6 carbon atoms, or represent straight-chain or branched alkoxy having 1 to 6 carbon atoms, or represent phenylalkyl, phenyl or phenoxy having if appropriate 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or Le A 29 399 13- I halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, A represents a divalent alkanediyl radical having 1 to 6 carbon atoms, and X' represents oxygen or sulphur, where
R
4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or represents straight-chain or branched alkyl having 1 to 6 carbon atoms which is optionally monosubstituted, suitable substituents being: hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 6 carbon atoms in the individual alkyl moieties;
R
4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, especially fluorine, chlorine, and/or bromine, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlroine and/or bromine, or represents in each case straightchain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 7 carbon atoms, each of which is optionally monosubstituted to pentasubstituted by identical or different substituents consisting of chlorine, bromine, Le A 29 399 methyl and/or ethyl, or furthermore represents phenyl or phenoxy each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/or straight- chain or branched alkyl having 1 to 4 carbon atoms,
S
R
or R 4 represents a radical of the formula
\R!
R
5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 6 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,Ndialkylamino having in each case 1 to 4 carbon atoms in the individual alkyl moieties;
R
5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, Le A 29 399 Y~I I N,N-dialkylamino or alkylideneimino having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 7 carbon atoms which is in each case optionally monosubstituted to pentasubstituted by identical or different substituents consisting of chlorine, bromine, methyl and/or ethyl, or furthermore represents phenyl or phenoxy each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms,
R
6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, or represents a radical
R"
of the formula __i
'R
R
7 represents straight-chain or branched alkyl having 1 to 6 carbon atoms or represents cycloalkyl having 3 to 7 carbon atoms,
R
8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represent cycloalkyl having Le A 29 399 16h- 3 to 7 carbon atoms, or represent phenylalkyl or phenyl having if appropriate 1 to 4 carbon atoms in the straight-chain or branched alkyl Smoiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/or straight- chain or branched alkyl having 1 to 4 carbon atoms; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted to tetrasubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 3 carbon afoms,
R'
0 and R" either independently of one another each represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 4 carbon atoms and 1 to 7 identical or different halogen; toms, especially fluorine, chlorine and/or bromine, or represent 17- L--LII I I- I in each case straight-chain or branched alkoxyalkyl or alkoxy having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 7 carbon atoms, or represent cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, or represent phenyl or phenylalkyl having if appropriate 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, or represent heteroaryl having 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for aryl and heteroaryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting ofhalogen and/ or straight- chain or branched alkyl having 1 to 4 carbon atoms; or R'O and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted to tetrasubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 3 carbon atoms, and
SX
2 represents oxygen or sulphur.
18- Very particularly preferred compounds of the formula are those in which Het represents a heterocycle of the formula R R R /N
_=N
or R 7
X
I I
R
2 and R3 independently of one another each represent fluorine, chlorine or bromine, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 4 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 4 carbon atoms, or represent straight-chain or branched alkoxy having 1 to 4 carbon atoms, or represent phenylalkyl, phenyl or phenoxy having if appropriate 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; A represents a divalent alkanediyl radical having 1 to 4 carbon atoms, and Le A 29 399 19- I 0 X' represents oxygen or sulphur, where
R
4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms which is optionally monosubstituied, suitable substituents being: hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 4 carbon atoms in the individual alkyl moieties;
R
4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represents halogenoa- Ikyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents in each case straight-chain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 6 carbon atoms, or furthermore represents phenyl or phenoxy, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different Ssubstituents consisting of fluorine, chlorine, bromine, methyl and/or SLe A 29 399 I i ethyl;
R!
or R 4 represents a radical of the formula 'R9
R
5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,Ndialkylamino having in each case 1 to 3 carbon atoms in the individual alkyl moieties;
R
5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N,N-diaikylamino or alkylideneimino having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 6 carbon atoms, or furthermore represents phenyl or phenoxy each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which Sis optionally monosubstituted to disubstituted by identical or different Le A 29 399 21-
I
suustituentA consisting of fluorine, chlorine, bromine, methyl and/or ethyl;
R
6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, or represents a radical
R"
of the formula _W
R
7 represents straight-chain or branched alkyl having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms,
R
8 and R 9 either independently of one another each represent hydrogen, or represent straight-chai. or branched alkyl having 1 to 4 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represent cycloalkyl having 3 to 6 carbon atoms, or represent phenylalkyl or phenyl having if appropriate 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; Le A 29 399 -22-
A'
or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted or disubstituted by identical or different substituents consisting of methyl and/or ethyl,
R'
0 and R" either independently of one another each represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlorine and/ or bromine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms, especiallyfluorine, chlorine and/or bromine, or represent in each case straight-chain or branched alkoxyalkyl or alkoxy having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 6 carbon atoms, or represent cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety, or represent phenyl or phenylalkyl having if appropriate 1 to 3 carbon atoms in the straight-chain or branched alkyl moeity, each of which is optionally monfosubstituted or disubstituted by "',entical or different substituents, or represent heteroaryl having 2 to 5 carbon atoms and 1 to 3 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for aryl and/or heteroaryl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or tbutoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, 23r I I 2 methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; or R'O and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur vAich is optionally monosubstituted or disubstituted by identical or different substituents consisting of methyl and/or ethyl, and X represents oxygen or sulphur.
Apart from the compounds listed for the Preparation Examples, specific mention may be made of the following substituted triazolinones of the general formula LeA29 399 -24- 7- sil -I It R I 2 X "MN-A-Si-R 13
R
(I)
R
3
A
N'
0N~
C
2
H
5 -CH2-
(?QKOC
N,~
CH
3
OH
3
CH
3 n-C 3
H
7
-OH
2 0 OH3 n-C 3
H
7 CH2' 0 n-C 3
H
7
-(OH
2 3 0 Le A29 399 Bl e t 0l A c-
C
2 115
C
2 H5
*C
2 Hi5 ~l2 al C3C 2 HS -(CH23- 0 C6CS C61i5 C61i5 -(Cli2)3- 0 NR CH3 Cfl 3 C H2- 0 CH3 CH3 CE{3 -Cl~r __LeA29 3 -26- ERet Rl R 2
R
3 A XI q-c-o
CH
3
CH
3 CH 3
-CH
2 s
H
3 0
G'
N'2 0N~
C
2
H
5
C
2
H
5
-O-
cI -(CH 2 3 0
CH
3
CH
3
C
2
HS-O-
CH
3
CH
3
CI
CH
3
CH
3
CI
-CH
2 0
-CH
2 0
-CH
2 0 27 Het RIR 2
R
3 A XI q C 2
H
5
C
2
H
5
OH
3
-CH
2 0 )-m
I
C
2
HS
NNXo l CI
-CH
2 0
-OH
2 0 I; G N a C 3
C
2
H
5 F \F H 3
-OH
2 0
N
N)~0
-OH
2 0 Le A 29399 2 28- Ret
R
3
X
A\
CH
3
CH
3 C25
CH
2 0 il q CH 3
CH
3
CH
3
-CH
2 0 4c
CH
3
CH
3
C
6
H
5 CH. 0
CH
3
CH
3
CH
3
-CH
2 0
F
2 a _T a CH 3
CH
3
CH
3
(CH
2 3 0 0' Le A29-39 29 Het ol N F, W'-
N'
RI R 2
R
3
CH
3
CH
3
-CH
2
-CH=CH
2
CH
3
CH
3
-CH
2 0 Gl F~ ~~N0
C
2
H
5 -Cu 2 0
CH
3 CH3-0- CH 3
-(OH
2 3 0 Le A..29399 -30
I
Bet RI R 2
R
3 A Xl- H a CH3
CH
3 i-C 3
H
7
-CH
2 0 H CH 3
CH
3 0H3 -CH 2 0
CH
3
CH
3
CH
3
-CH
2 0 Ne
CH
3
GB
3
CH
3
-CH
2 0
N'
CH
3
CH
3
CH
3
-GB
2 0
'NN)'
Le A29 399 31- KAON/c R3A XI
OH
3
-OH
2 0 OC; H 3
H
2 N-Cf8 2 n.OqH CH3 (CE;V N'N
OH
3
CH
3
OH
3
OH-
3
-OH
2 0
-OH
2 0
-OH
2 0
-OH
2 0 qv c
N'
be A 29399 2 32- 0, Het RR2
R
3 A X cnNF H 3 OH 3 0113
-OH
2
CH
3 0113
OH
3 -OH 2 0 KNo ")2N>7C
CH
3 0113
CH
3 0 011C3 0113 013 -0112- 0 OF-- 'a
H
3 CH 3 0113 -0112- 0 Le A 29399 33- Bet RI
R
2 R3A
CH
3 CR 3 CH 3 -CH 2 0 Using for example, l-chlorocarbonyl-3-dimethylamino4methy- 1,2,4one and trimethylsilylmethylamine as starting materials, the course of reaction of process according to the invention can be represented by the following equation: 113--N C- N'c N" 0 -HCI base l~
IC
Using for example, 3- dimethylamino-2-methylb 1,2A4-triazolin- 5- one and trimethylsilylmethyl isocyanate as starting materials, the course of reaction of process according to the invention can be represented by the following equation: Le A29 399 3 34- I N -=C=--N-CE-Si-C H
N
H4C-N 0 'NH-C^-Si-0^ A general definition of the l-chloro(thio)carbonyltriazolinones required as starting materials for carrying out process according to the invention is given by the formula In this formula (II) Het and X' preferably represent those radicals which have already been mentioned, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred for these substituents.
The l-chloro(thio)carbonyltriazolinones of the formula (II) are known.
(cf. e.g. EP 431 390; EP 283 876; EP 298 371).
A general definition of the amines also required as starting materials for carrying out process according to the invention is given by the formula (III). In this formula (III) R 2
R
3 and Apreferably represent those radicals which have already been mentioned, in connection with the description of the compounds of the formula according to the invention, as being preferred for these substituents.
The amines of the formula (III) are known. or are obtainable in analogy to known methods (cf e.g J. Amer. Chem. Soc., 213867 [1951]; Synth.
Le A 29 399 I Commun., 1, (16-17) 1975-1978).
A general definition of the 1-unsubstituted triazolinones required as starting materials for carrying out process according to the invention is given by the formula In this formula (IV) Het preferably represents those radicals which have already been mentioned, in connection with the description of the substances of the formula (I) according to the invention, as being preferred for these substituents.
The 1-unsubstituted triazolinones of the formula (IV) are known or are obtainable in analogy to known methods (cf e.g. EP 283 876; EP 431 390; EP 298 371).
A general definition of the iso(thio)cyanates also required as tarting materials for carrying out process according to the invention is given by the formula In this formula R 1
R
2
R
3 A and X' preferably represent those radicals which have already been mentioned, in connection with the description of the substances of the.formula
(I)
according to the invention, as being preferred for these substituents.
The iso(thio)cyanates of the formula are known or are obtainable in analogy to known methods (cf e.g. Zh. Obshch. Khim. 38, 1179-1185 [1968]; Zh. Obshch. Khim. 31, 1383-1385 [1967]; J. Org. Chem. 9, 2688-2691 [1984]).
Suitable diluents for carrying out process according to the invention are inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene Le A 29 399 36- LP1 dl M v glycol dimethyl or diethyl ether; ketones such as acetone, butanone or methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile or benzonitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate, or bases such as pyridine.
Process according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. Suitable such auxiliaries are all conventional inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide or else ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, or ammonium carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, or ammonium acetate, and tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene
(DBU).
It is also possible to employ the amine of the formula (III) used as reactant, in a corresponding excess, simultaneously as reaction auxiliary.
When carrying out process according to the invention the reaction temperatures can be varied over a relatively wide range. The process is in general carried out at temperatures of between 0 0 C and 150 0
C,
preferably at temperatures of between 10 0 C and To carry out process according to the invention, in general from to 5.0 mol, preferably from 1.0 to 2 mol, of amine of the formula (III) and, if appropriate, from 1.0 to 5.0 mol, preferably from 1.0 to 2 mol, of Le A 29 399 37base as reaction auxiliary are employed per mole of 1chloro(thio)carbonyltriazolinone of the formula The implementation of the reaction and the working-up and isolation of the reaction products are carried out by known methods (cf in this respect, for example, EP 283 876 or the Preparation Examples).
Suitable diluents for carrying out process according to the invention are inert organic solvents. It is preferred to use the soivents listed in the descriptiun of the implementation of process according to the invention.
Process according to the invention may if desired be carried out in the presence of a suitable, basic reaction auxiliary. Suitable such auxiliaries are all conventional inorganic or organic bases. Preference is given to using tertiary amines such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, piperidine, Nmethylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
The addition of basic reaction auxiliaries, however, is not absolutely necessary.
When carrying out process according to the invention the reaction temperatures can be varied over a relatively wide range. The process is in general carried out at temperatures of btween 0°C and +150C, preferably at temperatures of between +40°C and 120°C.
Process according to the invention is usu' y carried out under atmospheric pressure. However, it is also possible to work under elevated or reduced pressure.
To canry out process according to the invention, in general from 1,O LLeA-29-3 -38-
I--
t to 5.0 mol, preferably from 1.0 to 2.5 mol, of iso(thio)cyanate of the formula and, if appropriate, from 0.01 to 5.0 mol, preferably from 0.1 to 2.5 mol, of base as reaction auxiliary are employed per mole of 1unsubstituted triazolinone of the formula (IV).
The implementation of the reaction and the working-up and isolation of the reaction products are carried out by known methods (cf. in this respect, for example, EP 283 376 or the Preparation Examples).
The end products of the formula are purified with the aid of conventional methods, for example by column chromatography or by recrystallization.
Characterization is made by means of the melting point or, in the case of compounds which do not crystallize, with the aid of proton nuclear magnetic resonance spectroscopy ('H-NMR).
The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants arid, especially, as weedkillers. By weeds, in the broadest sense, there are to be understood all plants which growin locations where they are not wanted.
Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants: Dicotyledon weeds ofthe genera: Sinapis, Lepidium, Galium, Stellaris Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Le A 29 3-9-2 39- II i LL I I I~ Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotvledon cultures ofthe genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledon weeds of the gnera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum,.
Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total control ofweeds, for example on industrial terrain and rail tracks, and on paths and squares m~Wt and without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, and for the selective combating of weeds in annual cultures.
In this context the active compounds according to the invention can be employed with particular success to combat mono- and dicotyledon Le A 29 399 BI~ "I 117 weeds in monocotyledon crops such as, for example, maize.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. Suitable liquid solvents are in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide or dimethyl sulphoxide, as well as water.
Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco Le A 29 399 -41- ~YICI I I I r stalks; suitable emulsifying and/or foam-forming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products; suitable dispersing agents are: for example lignin sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives may be mineral and vegetable oils.
It is possible to use coloiants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations contain in general between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and The active compounds according to the invention, as such or in the form of their formulations, can also be used, for combating weeds, as mixtures with known herbicides, finished formulations or tank mixes being possible.
Suitable herbicides for the mixtures are known herbicides, such as, for example, anilides, for example diflufenican and propanil; arylcarboxylic acids such as dichloropicolinic acid, dicamba or picloram; aryloxyalkanoic acids such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, such as Le A 29 3- 2 -42- 4, -1 Idiclofopmethyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop- methyl and quizalofop-ethyl; azinones such as chioridazone and norilurazone; carbamates such as chiorpropham, desmedipham, phenmedipham and propham; chioroacetanilides such as alachior, acetochior, butachior, metazachior, metolachior, pretilachior and propachor; dinitroanilines such as oryzalin, pendimethalin and trifluralin; diphenyl ethers such as acifluorfen, bifenoxy fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as chiorotoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, such as imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, such as bromoxynil, dichiobenil and ioxynil; oxyacetamides, such as mefenacet; suiphonylureas, such as amidosulfuron, bensulfaron-methyl, chiorimuron-ethyl, chiorsulfon, cinosulfiron, metsulfiron- methyl, nicosulfuron, primisulfuiron, pyrazosulfuron-ethyl, thifensulfiron-rnethyl, triasulfuron and tribenuronmethyl; thiolcarbamates, such as butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, such as atrazine, cyanazin, simazin, simetryne, terbutryr and terbutylazine; triazinones, such as hexazinon, metamitron and metribuzine; and others such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, -difenzoquat, dithiopyr, ethoflmesate, fluorochioridone, glufosinate, glyphosate, isoxaben, pyridate, quinchiorac, quinmerac, suiphosate and tridiphane.
A mixures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes Le A 29 394 -43and granules. They are used in the customary manner, for example by watering spraying, atomizing or scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants.
They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 0.01 and 10 kg of active compound per hectare of soil surface, preferably between 0.05 and 5 kg per hectare.
The preparation and the use of the active compounds according to the invention are evident from the following examples.
Le A 29 394 44- I- I -II I Preparation Examples: Example 1: cHf 3
YCN'
N
o O1- \MN-a;-J a (Process a) A solution of 2.68 g (0.025 mol of trimethylsilylmethylamine and 2.53 g (0.025 mol) of triethylamine in 50 ml of acetonitrile is added dropwise with stirring at room temperature to 5.1 g (0.025 mol) of 1-chlorocarbonyl-3-dimethylamino-4-methyl-1, 2 ,4-triazolin-5-one in 100 ml of acetonitrile and, after addition is complete, the mixture is stirred at room temperature for 60 minutes. For working up, precipitated triethylamine hydrochloride is filtered off the filtrate is concentrated in vacuo, and the residue is taken up in 150 ml of dichloromethane, washed with three times 50 ml ofwater, dried over sodium sulphate and again concentrated in vacuo. The residue is recrystallized from cyclohexane.
g (59% of theory) are obtained of 3 -dimethylamino-4-methyl- 1- (trimethylsilylmnethyl-arninocarbonyl)- 1, 2 ,4-triazolin-5-one with a melting point of 79-81 C.
Le A 29 394 'r le Example 2: 0 N
-N
Uc^\^0 C I Process (b) 3.87 g (0.03 mol) of trimethylsilyl isocyanate and 3 drops of 1,8diazabicyclo- [5.4.0]-undec-7-ene (DBU) are added at room temperature with stirring to 5.25 g (0.03 mol) of 2-methyl-3-(4-morpholinyl)-(1H)- 1,2,4-triazolin-5-one in 100 ml of acetonitrile, the mixture is subsequently stirred at room temperature for 4 hours and is then concentrated in vacuo, and the residue is recrystallized from cyclohexane/ethyl acetate g (69% of theory) are obtained of 2-methyl-3-(4-morpholinyl)-1- (trimethylsilylmethyl-aminocarbonyl)-1,2,4-triazolin-5-one with a melting point of 133-134C..
In a corresponding manner, and in accordance with the general preparation data, the following substituted triazolinones of the general formula are obtained: Le A 29 394 -46 FLAt
R
*X NNl ASi-R
(I)
13
R
Ex. No. Het 1AS- 2 physical properties N l 0 ntp.99-100 0
C
4 a-S l 0 fl2p. 130-132 0
C
(GEj OqA 0 mp. 46-47 0
C
N
-n9-Si.CAI 0.6-0.7;
N'
OCA 1. 18-1.23; I 2.65; 3.20 Le A 29399 4 -47- Ex. No.
R
1 2 -A-Si-R XI physical properties 613 613 613
CF;
o imp. 79-801C o imp. 139-140*C o mrp. 140-141*C o imp. 81-83*C o rmp103-104*C 0 imp. 63-64TC
N'
12 !q C 48 ii Ex. No.
1
R
I 2 -A-Si-R 1e
X
1 physical properties 13 H CI-;a n.p. 115-116 0
C
LoZ P lil~ NYX t 14 16 BrC 16 Br KA4~ N e
C
CI;
aJ 3 ~~if GhS -aCE &13b~a o imp.79-.81 0
C
o Imp. 87-891C o mp, 143-145 0
C
o 1H.N4*) 1.15-1.20; 3.22 o m~p. 92-93 0
C
NR
-N
.olt-xO Le A 29 399 -49- Ex. No.
C
4
H
qq N=C\
A
4Cy) i-C0
R
i-R2 aI3 &J3 physical XI properties 0 xdp,167-168 0
C
o nap. 50-5 1 C 0.9-0.93; 1.18-1.2; 1.9; 2.3-2.32 0 IMp. 68-69-C 0 iff.p. 117-118 0
C
Lg A 29399 Ex. No.
1
R
2
X
1 physical properties 2.0,2.35-2.38; 2.85 N4 -0 26
IA
27 NC,_n-Cl
L'
29 IC6\ dli dli
CI
clt o 1H-NMR 0.8; 2.8-2.82; o 1H-NW.
0.8; 1.25-1.28; 2.77-2.8 o H-NNR*): 0.85-0.92; 2.75-2.8; 3.63-3.7 o rap. 88-90 0
C
0 rap. 158-160C Le. A 29 39 51pm Ex. No, -1
R
R
XI physical xl roperties Br I- 0 M.P. 94-95 0
C
6;3 31 40Dc a 32 C1 f 33 w/I
N,
0 M.P. 1 12 0
C
013 6;3 0 imp. 1210C 0 m.p. 125 0
C
Le A 29 399 52
V
Ex, No.
I
R
A-Si--Rk k q 3 XI physical properties 0 oil 36 (a 2 N 0cH
NIX
S IH-NM*): 3.04; 3.08- 3. 10; 3.30; 11.0 *)The 'H-NMIR spectra wre recorded in deuterochioroform (CD Cl 3 or l eutero dim ethylsuiphoxide (DMSO- d 6 with tetramethylsilane (TMS) as internal standard, The value given is the chemical shift, 8, in ppm.
LeA 2939-9 53 Use Examples: Jn the following Use Examples the compound indicated below wvas employed as comparison substance:
_N
(A)
2- Methyl- 3- dimethylamino- 1 dimethyl- 1 propyl)aminocarbonyl]- 1 ,2,4-triazolin- 5- one (knoxwn from EP 431 390) Le A29 399 54- Example A: Pre-emergenc, test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalk aryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in damage in comparison to the development of the untreated control.
The figures denote: 0% no action (like untreated control) 100% total destruction In this test, for example, the compound according to Preparation Example 3 exhibits a marked superiority in activity, and also a considerably improved selectivity by crop plants, in relation to the prior art.
Le A 29 399 TableA.- Pre-emergence test! greenhouse Active cempound (ala (knov~n) (Exampfe 3) Application rate 1ng/a125 125 Maize Echinochloa Abuthilon Cassia Chenopod1ium Galium Sinapis Solanum 0 100 100 100 Le A29 399 56 Example B: Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which are 5 15 cm high are sprayed with the preparation of the active compound so as to apply the particular amounts of active compound desired per unit area. After three weeks, the degree of damage to the plants is rated in damage in comparison to the development of the untreated control.
The figures denote: 0% no action (as in the untreated control) 100% total destruction In this test, for example, the .ompound according to Preparation Example 3 exhibits a marked superiority in activity, and also a considerably improved selectivity by crop plants, in relation to the prior art.
57- Table B: Post-emeigence test! Gnenhouse Active compound o, 1
N
(knov~n) (Example 3) Application rate in gf ha 125 125 Maize Galitum Stellafla 'Viola Le A 29399 58
Claims (6)
1. Substituted triazolinones of the general formula (I) I R X 'N-A-Si-R (1) 13 R in which Het represents a heterocycle of the formula R 4 R 5 R6 1 IN or R7 R 2 and R 3 independently of one another each represent halogen, alkyl, alkenyl, alkinyl or alkoxy or represent in each case optionally substituted arylalkyl, aryl or aryloxy, A represents a divalent alkanediyl radical, and X' represents oxygen or sulphur, where R 4 represents hydrogen, halogen, cyano or nitro or represents optionally substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl, halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, or represents a radical of the formula Le A 29 399-PCT 59- R -Y, R 9 R 5 represents hydrogen or cyano, or represents optionally substituted alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or aminocarbonyl, or represents amino, N-alkylamino, N,N- dialkylamino or alkylideneimino, or represents in each case option- ally substituted cycloalkyl, aryl or aryloxy, R 6 represents alkyl, alkoxy or alkylthio, or represents a radical of the RD formula 'R" R 7 represents alkyl or cycloalkyl, R 8 and R 9 either independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case optionally substituted arylalkyl or aryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, R' 0 and R" either independently of one another each represent alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each case optionally substituted aryl, arylalkyl or heteroaryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, and X 2 represents oxygen or sulphur. Le A 29 399
2. Substituted triazolinones of the general formula according to Claim 1, characterized in that Het represents a heterocycle of the formula 4 5 6 R R! R! R or R R 2 and R 3 independently of one another each represent fluorine, chlorine, bromine or iodine, or represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 8 carbon atoms, or represent straight- chain or branched alklnyl having 2 to 8 carbon atoms, or represent straight-chain or branched alkoxy having 1 to 8 carbon atoms, or represent arylalkyl, aryl or aryloxy having in each case 6 to 10 carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms, Le A 29 399 61- A represents a divalent alkanediyl radical having 1 to 8 carbon atoms, and X' represents oxygen or sulphur, where R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano or nitro, or represents straight-chain or branched alkyl which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 8 carbon atoms in the individual alkyl moieties; R 4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, in particular fluorine, chlorine, bromine and/or iodine, or represents in each case straight-chain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 8 carbon atoms in the individual alkyl moieties,.or moreover represents cycloalkyl having 3 to 8 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/ or straight-chain or branched alkyl having 1 to 4 carbon atoms, or furthermore represents aryl or aryloxy having in each case 6 to 10 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each Le A 29 399 -62- case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms, R! or R 4 represents a radical of the formula _W, '9 R 5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 8 carbon atoms which is optionally inonosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 8 carbon atoms in the individual alkyl moieties; R 5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N- alkylamino, N,N-dialkylamino or alkylideneimino having in each case 1 to 8 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 8 carbon atoms, each ofwhich is optionally monosubstituted or polysubsiituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, or furthermore Le A 29 399 63 I represents aryl or aryloxy having in each case 6 to 10 carbon atoms, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain o branched alkyl, alkoxy or alkythio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical of different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms, R 6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 8 carbon atoms, or represents a R radical of the formula 'Rn R 7 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or represents cycloalkyl having 3 to 8 carbon atoms, R 8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 8 carbon atoms, or each represent straight-chain or branched alkenyl or alkinyl having in each case 2 to 8 carbon atoms, or represent cycloalkyl having 3 to 8 carbon atoms, or represent arylalkyl or aryl having in each case 6 to 10 carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or Le A 29 396 -64- polysubstituted by identical or different substituents, suitable substituents for aryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 to 2 further heteroatoms in particular nitrogen, oxygen or sulphur and which is optionally monosubstituted or polysubstituted by identical or different substituents consisting ofstraight-chain or branched alkyl having 1 to 4 carbon atoms, R'I and R" either independently of one another each represent straight- chain or branched alkyl having 1 to 8 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkiny having in each case 2 to 8 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, especially fluorine, chlorine, bromine and/or iodine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms, especially fluorine, chlorine, bromine and/or iodine, or represent in each case straight-chain or branched alkoxyalkyl or alkoxy having in each case i to 8 carbon atoms in the individual alkyl moieties, or Le A 29 399 I represent cycloalkyl having 3 to 8 carbon atoms, or represent cycloalkylalkyl having 3 to 8 carbon atoms in the cycloalkyl moiety and 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, or represent aryl or arylalkyl having in each case 6 to carbon atoms in the aryl moiety and if appropriate 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or polysubstituted by identical or different substituents, or represent heteroaryl having 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms in particu'ar nitrogen, oxygen and/or sulphur which is optic. ally monosubstituted or polysubstituted by identical or different substituents, suitable substituents for aryl and heteroaryl being in each case: halogen, cyano, nitro, in ecch case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy. halogenoalkylthio having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 6 carbon atoms; or R" and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 to 2 further heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or polysubstituted by identical or different substituents consistingof straight-chain or branched alkyl having 1 to 4 carbon atoms, and X 2 represents oxygen or sulphur. Le A 29 399 66- La s
3. Substituted triazolinones of the general formula according to Claim 1, characterized in that Het represercs a heterocycle of the formula R 4 R! R 6 R 1 R 2 and R 3 independently of one another each represent fluorine, chlorine or bromine, or represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 6 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 6 carbon atoms, or represent straight- chain or branched alkoxy having 1 to 6 carbon atoms, or represent phenylalkyl, phenyl or phenoxy having if appropriate 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, Le A 29 399 -67- A represents a divalent alkanediyl radical having 1 to 6 carbon atoms, and X' represents oxygen or sulphur, where R 4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or represents straight-chain or branched alkyl having 1 to 6 carbon atoms which is optionally monosubstituted, suitable substituents being: hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 6 carbon atoms in the individual alkyl moieties; R 4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents in each case straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, especially fluorine, chlorine, and/or bromine, or represents in each case straight-chain or branched halogenoal.enyl or halogenoalkinyl having in each case 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents .in each case straight-chain or branched aikoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 7 carbon atoms, each of which is optionally monosubstituted to pentasubstituted by identical or different substituents consisting of chlorine, bromine, methyl and/or ethyl, or furthermore represents phenyl or phenoxy each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, Le A 29 399 -68- alkoxy or alkylthio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, R or R 4 represents a radical of the formula \R9 R S represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 6 carbon atoms which is optionally monosubstituted or polysubstituted by identical or diffeient substituents, suitable substituents being fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N- dialkylamino having in each case 1 to 4 carbon atoms in the individual alkyl moieties: R S moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N- alkylamino, N,N-dialkylamino or alkylideneimino having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 7 carbon atoms which is in each case optionally monosubstituted to pentasubstituted by identical or different substituents consisting of chlorine, bromine, methyl and/or ethyl, or furthermore represents phenyl or phenoxy Le A 29 399 69- each of which is optionally monosubstituted to trisubstituted by identical or different substitueiits, suitable substituents for phenyl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms, R 6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 6 carbon atoms, or represents a R radical of the formula 'Rn R 7 represents straight-chain or branched alkyl having 1 to 6 carbon atoms or represents cycloalkyl having 3 to 7 carbon atoms, R 8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 6 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represent cycloalkyl having 3 to 7 carbon atoms, or represent phenylalkyl or phenyl having if appropriate 1 to 4 carbon atoms in the straight- chain or branched alkyl moiety, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for phenyl being in each case: Le A 29 399 halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted to tetrasubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 3 carbon atoms, R' 0 and R" either independently of one another each represent straight- chain or branched alkyl having 1 to 6 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represent straight-chain or branched halogenoalkyl.having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represent in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represent in each case straight- chain or branched alkoxyalkyl or alkoxy having in each case 1 to 6 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 7 carbon atoms, or represent cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atom.st in the straight-chain or branched alkyl moiety, or represent phenyl or Le A 29 399 71- phenylalkyl having if appropriate 1 to 4 carbon atoms in the straight- chain or branched alkyl moeity, each of which is optionally monosubstituted to trisubstituted by identical or different sub- stituents, or represent heteroaryl having 2 to 9 carbon atoms and 1 to 3 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents for aryl and heteroaryl being in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkythio having in each case 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxy A.yl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents consisting of halogen and/or straight-chain or branched alkyl having 1 to 4 carbon atoms; or R'O and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted to tetrasubstituted by identical or different substituents consisting of straight-chain or branched alkyl having 1 to 3 carbon atoms, and X? represents oxygen or sulphur.
4. Substituted triazolinones of the general formula according to Claim 1, characterized in that Het represents a heterocycle of the formula Le A 29 399 -72- 4 5 6 R R or R R 2 and R 3 independently of one another each represent fluorine, chlorine or bromine, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent straight-chain or branched alkenyl having 2 to 4 carbon atoms, or represent straight-chain or branched alkinyl having 2 to 4 carbon atoms, or represent straight- chain or branched alkoxy having 1 to 4 carbon atoms, or represent phenylalkyl, phenyl or phenoxy having if appropriate 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; A represents a divalent alkanediyl radical having 1 to 4 carbon atoms, and X' represents oxygen or sulphur, where io A 29 399 73- I R 4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms which is optionally monosubstituted, suitable substituents being: hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N-dialkylamino having in each case 1 to 4 carbon atoms in the individual alkyl moieties; R 4 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represents halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represents in each case straight-chain or branched alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 6 carbon atoms, or furthermore represents phenyl or phenoxy, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; Le A 29 399 -74- t R or R 4 represents a radical of the formula '9 R 5 represents hydrogen, cyano, amino or aminocarbonyl, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, hydroxyl, cyano, amino, in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N,N- dialkylamino having in each case 1 to 3 carbon atoms in the individual alkyl moieties; R 5 moreover represents in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represents in each case straight-chain or branched alkoxy, alkoxycarbonyl, N- alkylamino, N,N-dialkylamino or alkylideneimino having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or furthermore represents cycloalkyl having 3 to 6 carbon atoms, or furthermore represents phenyl or phenoxy each of which is option- ally monosubstituted nr disubstituted by identical or different subtituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; Le A 29 399 R 6 represents in each case straight-chain or branched alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, or represents a RD radical of the formula 'R" R 7 represents straight-chain or branched alkyl having 1 to 4 carbon atoms or represents cycloalkyl having 3 to 6 carbon atoms, R 8 and R 9 either independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represent cycloalkyl having 3 to 6 carbon atoms, or represent phenylalkyl or phenyl having if appropriate 1 to 3 carbon atoms in the straight- chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, suitable substituents for phenyl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; or R 8 and R 9 together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted or Le A 29 399 -76- disubstituted by identical or different substituents consisting of methyl and/or ethyl, R' 0 and R" either independently of one another each represent straight- chain or branched alkyl having 1 to 4 carbon atoms, or represent in each case straight-chain or branched alkenyl or alkinyl having in each case 2 to 4 carbon atoms, or represent straight-chain or branched halogenoalkyl having 1 to 3 carbon atoms and 1 to 7 identical or different halogen atoms, especially fluorine, chlorine and/ or bromine, or represent in each case straight- chain or branched halogenoalkenyl or halogenoalkinyl having in each case 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms, especially fluorine, chlorine and/or bromine, or represent in each case straight- chain or branched alkoxyalkyl or alkoxy having in each case 1 to 4 carbon atoms in the individual alkyl moieties, or represent cycloalkyl having 3 to 6 carbon atoms, or represent cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety, or represent phenyl or phenylalkyl having if appro- priate 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, each of which is optionally monosubstituted or disubstituted by identical or different substituents, or represent heteroaryl having 2 to 5 carbon atoms and 1 to 3 identical or different heteroatoms in particular nitrogen, oxygen and/or sulphur which is optionally monosubstituted or disubstituted by identical or different sub- stituents, suitable substituents for aryl and/or heteroaryl being in each case: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i- propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, methoximinoethyl, ethoximinomethyl, Le A 29 399 77- c ethoximinoethyl or phenyl which is optionally monosubstituted to disubstituted by identical or different substituents consisting of fluorine, chlorine, bromine, methyl and/or ethyl; or RI 0 and together with the nitrogen atom to which they are attached, represent a saturated five- to seven-membered heterocycle which may optionally contain 1 further heteroatom in particular nitrogen, oxygen or sulphur which is optionally monosubstituted or disubstituted by identical or different substituents consisting methyl and/or ethyl, and X represents oxygen or sulphur. Process for the preparation of substituted triazolinones of the general formula (I) I-t 1 R R X "N-A-Si-R (I) 13 R Het represents a heterocycle of the formula R! R! R 6 4 5 6 or RX2 R 2 and R 3 independently of one another each represent halogen, alkyl, alkenyl, alkinyl or alkoxy or represents in each case optionally substituted arylalkyl, aryl or aryloxy, A represents a divalent alkanediyl radical, and Le A 29 399
78- X represents oxygen or sulphur, where R 4 represents hydrogen, halogen, cyano or nitro or represents optionally substituted alkyl, or represents alkenyl, alkinyl, halogenoalkenyl, halogenoalkinyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl, or represents in each case optionally substituted cycloalkyl, aryl or aryloxy, or represents a radical of the formula \R7 R 5 represents hydrogen or cyano, or represents optionally substituted alkyl, or represents alkenyl, alkinyl, alkoxy, alkoxycarbonyl or aminocarbonyl, or represents amino, N-alkylamino, N,N- dialkylamino or alkylideneimino, or represents in each case option- ally substituted cycloalkyl, aryl or aryloxy, R 6 represents alkyl, alkoxy or alkylthio, or represents a radical of the R formula i 'R" R 7 represents alkyl or cycloalkyl, R 8 and R 9 either independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl or represent in each case optionally substituted arylalkyl or aryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, Le A 29 399
79- R 1 and R" either independently of one another each represent alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, alkoxyalkyl, alkoxy, cycloalkyl or cycloalkylalkyl or represent in each case optionally substituted aryl, arylalkyl or heteroaryl, or, together with the nitrogen atom to which they are attached, represent an optionally substituted heterocycle, and X represents oxygen or sulphur, characterized in that a) 1-chloro(thio)carbonyltriazolinones of the formula (II) I X IC in which Het and X' have the meanings giv; above are reacted with amines of the formula (III) I 2 R HN-A-Si-R! 13 R (ff in which R 2 R 3 and A have the meanings given above, optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary, or if Le A 29 399 81 b) 1-unsubstituted triazolinones of te formula (IV) Het-H (IV) in which Het has the meaning given above are reacted with iso(thio)cyanates of the formula (V) oc r o o r* r e c R SC I-A-S 2 XC=N-A-S i--R in which R 2 R 3 A and X' have the meanings given above, optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary. 6. Herbicidal compositions, characterized in that they contain at least one substituted triazolinone of the general formula accordingto Claims 1 to 7. Method of combating unwanted plants, characterized in that substituted triazolinones of the general formula according to Claims 1 to 5 are allowed to act on plants and/or their habitat. 82 8. Process for the preparation of herbicidal compositions, chacterized in that substituted triazolinones of the general formula according to Claims 1 to 5 are mixed with extenders and/or surface-active substances. DATED this 19th day of September, 1995. BAYER AKTIENGESELLSCHAFT By Its Patent Attorneys 15 DAVIES COLLISON CAVE go** *o *go• p:\wpdocs\grs\543522\kd Ip I I INTERNATIONAL SEARCH REPORT n Intrr al Application No PCT/EP 93/02705 A. CLASSIFICATION OF SUBJECT MATTER IPC 5 C07F7/08 C07F7/18 A01N55/00 According to International Patent Classificaton (IPC or to both national classification and IPC B. FIELDS SEARCHED Mimn Am documentation searched (classificaon system followed by classficaton symbols) IPC 5 C07F AO1N Documentation searched other than minmmum documentation to the extent that such documents are included in the fields searched Electronic data base consulted during the ternational search (name of data base and, where practical, search terms used) C. DOCUMENTS CONSIDERED TO BE RELEVANT Category Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No. A WO,A,89 00573 (AGROLINZ AGRARCHEMIKALIEN 1 GMBH) 26 January 1989 see the whole document A DE,A,41 09 671 (BAYER AG) 24 September 1,6 1992 see the whole document SFurther documents are listed in the continuation of box C. M Patent famlymembers ar listed in annex. Special categories of ated documents later document published after the international filing date A' document defining the general state of the art which is not or pnonty date and not in conflict with the application but consdered to be of partcular relevance cted to understand the princple or theory underlying the invention E' earlier docuent but pulished on or after the nternatonal "X document of particular relevance; the claimed Invention filing date cannot be considered novel or cannot be considered to L document which may throw doubts on prnonty claim(s) or involve an inventive step when the document is taken alone which is ated to establish the publication date of another d o p r t c atation or other special reason (as specified) Y document of partcular relevance; the claimed inventon n, cannot be considw-d to involve an inventive step when the document refernng to an oral disclosure, use, exhibition or document is comn ined with one or more other such docu- othe' means ments, such co oination being obvious to a person slalled document published pnor to the International filing date but m the art. later than the prnonty date claimed document member of the same patent family Date of the actual completon of the internatonal search Date of mailing of the international search report 7 December 1993 2 112. 93 Name and mailing address of the ISA Authorized officer European Patent Office, P.B. 5818 Patentlaan 2 NL 2280 HV Rl)swilk Tel. (+31-70) 340-2040, Tx. 31 651 epo nl, R l Fa (+31-70) 340-3016 Rinkel, L I- .LIdvu Iics act Jl Y~ rorm rPCllSA/210 (fec9na Ineet) (July 199) 111 11 INTERNATIION AL SEARCH REPORT -fomaton n ptet fmil mc =Inften Wa Application No fomaton n ptet fmil icrnaiPCT/EP 9 3/02705 Patent document I Publication IPatent famifly I Publication cited in search report d ate member(s) j date WO-A-8900573 26-01-89 DE-A- 3723246 26-01-89 AU-A- 1980388 13-02-89 EP-A- 0303802 22-02-89 DE-A-4109671 24-09-92 EP-A- 0505819 30-09-92 JP-A- 5112539 07-05-93 Form PCT/ISAI2IO (patent family annex) (July 1992) INTERNATIONALER RECHERCHENBERICHT In" iWes Aktenzechcn PCT/EP 93/02705 A. KLASSI2FIZIERUNG DES ANMELDUNGSGEGENSTANDES IPK 5 C077/08 C077/18 AOIN55/00 Nacts der Intersutionalen Patentkjaanfikation (IPK) oider nach der naionalen Kassifikation und der IPK B. RECHERCHIERTE GEBIETE Recherchierter Mindesspndioff (Klassifikationscystemn und Klasofikationssymbole) IPK 5 C07F A0iN Recherchiertc aber nscht zumn Mindecstpriltstoff geh~rende Vertflendichungcn, soweit die tinter die recherchiertan Gebiece fallen Wlhrend der internatonalen Recherche konsuluerte elcktrorischc Datenbank (Name der Datenbank und evil. verwendete Suchbegniffe) C. ALS WESENTLICH ANGESEHENE UNTERLAGEN Kategone' Bezeickintrig der Verbifentliehung, sowait erforderlich tinter Angabe der in Betracht kommnendcn Teile Batr. Anspruch Nr. A WO,A,89 00573 (AGROLINZ AGRARCHEMIKALIEN 1 GMBH) 26. Januar 1989 siehe das ganze Dokument A DE,A,41 09 671 (BAYER AG) 24. September 1,6 1992 siehe das ganze Dokument WiceVerdifentlichungen sind der Fortsetzung von Feld C zu MY Siehe Ahn aetaii ennhien vIn Ineeee e~te~cugnAh BEsondere Kategone ongieene n c~fnhhmc T' Spe Veroffientliebuitng, die nach dem, internationalen. Anidedawum Veroffentlichung, die den aligemncmen Stand der Technik definiert, oer dem Priontatr.daturn ver6ffcntbcht worden ist und mit der aber nicht als besonders bedeutsam anzusehen ist Anmeldung nicht kollidiert, sondemn wsr z=iVerstandrus des der E ~Jere Dounsnt, as edoh mt amode nah dm Inemaicnlen Erfindung zugridehecgenden Prunps cder der ibs zugruneleliegenden ltces okumn% as edoc crt a odr nah dm iternticalThe1one angegcoen it Anmieldedlaturn verffentlicht worden it *X Verdifentlachung von besondecr Bed;!utung; die beanaruchte ErfindunE V Verdffentiichtmig, die geelgnet ist, einen Priontitsanspruch zweifelhalt er- kann allein aufgrund dieser Verdffentlichung nicht al eu oder auf sichcinen zu lassen, cider durch die dlas Vcr~ffentlichungsdatm, cuier crfindenicher Titigkezt beruhend betrachtet werden ande'ren im Recherchenbencht genannten Veroffentliehung belegt werdeli Verdffentlichung von bcsonderer Bedcutung; die beansprucbte ErfindunE soil oder die aus einemn andereni besondereri Grund angegeben ist (wie kann nieht als auf erfinderischer 'l'tigkeit beruhtend betrachtet ausgeftlbrt) werden, wenn die Vcr6ffentliehung vut esner odes mebhreren anderen Veroffentlichung, die ich auf elne enfindliche Offenbanaing, Ver6(Tentliehungen diescr Kategorie in Verbindung gebracht wird und esne Benuizung, emne Ausstellung oder andere Maflnahmen bezieht diese Verbzindung ftlr ctnen Facbm=n naheltegend ast Verwffentlichung, die vor dem inteinationalen Anmnieclatumn, aber nach dern beanpruchten PnontAsdaw~m verffentlicht warden ist& Verdifentlichung, dite Mitglied derselben Patentfnlie ist Datum des Abschlusses der internatialen Recherche Absendedatarm des trternationalen Recherchenbencbts 7. Dezember 1993 I Name und Postanxtthnft der Interrnatonale Recherclicnbehdrde Bevollmichugter Bediensteter Europaiselies Patentamt, P.B. 5818 Patentlaan 2 NL.- 2280 HV Pijswilk Tel. (r31-70) 340-2040, Tx. 31651 po nl, Rne Fax 31.70) 340-3016 ikl L -rynblatt P JISA/210 (Blatt 1) (Jul! 1992) INTERNATIONA LER RECHERCHENBERICHT Angaben zu Vcr6ffcndtcbui...,i, die zur scibcn Patentrantilic gchora P tles 93/02705 Im Recherchenbericht Datum der Mirglied(er) der Datum der angef~hrtes Patentdokument Veroffentlichung k'awntfamilie Veroffendichung WO-A-8900573 26-01-89 DE-A- 3723246 26-01-89 AU-A- 1980388 13-02-89 EP-A- 0303802 22-02-89 DE-A-4109671 24-C'9-92 EP-A- 0505819 30-09-92 JP-A- 511253S 07-05-93 Formblatt PC771SAJ210 (Anhang Patentfamitle)(Juli 1992)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4234306 | 1992-10-12 | ||
DE4234306A DE4234306A1 (en) | 1992-10-12 | 1992-10-12 | Substituted triazolinones |
PCT/EP1993/002705 WO1994009012A1 (en) | 1992-10-12 | 1993-10-04 | Substituted triazolinones |
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 (en) |
JP (1) | JPH08505837A (en) |
AU (1) | AU664780B2 (en) |
BR (1) | BR9307225A (en) |
CA (1) | CA2146661A1 (en) |
DE (1) | DE4234306A1 (en) |
RU (1) | RU95113591A (en) |
WO (1) | WO1994009012A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN105358563B (en) | 2013-07-02 | 2018-03-30 | 四国化成工业株式会社 | Azoles silane compound, surface treatment liquid, surface treatment method and its utilization |
JP6071806B2 (en) * | 2013-08-27 | 2017-02-01 | 四国化成工業株式会社 | Azole silane compound, synthesis method of the compound and use thereof |
JP6071780B2 (en) * | 2013-07-02 | 2017-02-01 | 四国化成工業株式会社 | Azole silane compound, synthesis method of the compound and use thereof |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3723246A1 (en) * | 1987-07-14 | 1989-01-26 | Lentia Gmbh | NEW THIENYL AZOLYL METHYL SILANE |
DE4109671A1 (en) * | 1991-03-23 | 1992-09-24 | Bayer Ag | SUBSTITUTED TRIAZOLINONES |
JP2823614B2 (en) * | 1989-12-15 | 1998-11-11 | 株式会社日立製作所 | Gradation display method and liquid crystal display device |
-
1992
- 1992-10-12 DE DE4234306A patent/DE4234306A1/en not_active Withdrawn
-
1993
- 1993-10-04 EP EP93921909A patent/EP0663917A1/en not_active Ceased
- 1993-10-04 WO PCT/EP1993/002705 patent/WO1994009012A1/en not_active Application Discontinuation
- 1993-10-04 AU AU51106/93A patent/AU664780B2/en not_active Expired - Fee Related
- 1993-10-04 CA CA002146661A patent/CA2146661A1/en not_active Abandoned
- 1993-10-04 RU RU95113591/04A patent/RU95113591A/en unknown
- 1993-10-04 JP JP6509576A patent/JPH08505837A/en active Pending
- 1993-10-04 BR BR9307225A patent/BR9307225A/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
WO1994009012A1 (en) | 1994-04-28 |
DE4234306A1 (en) | 1994-04-14 |
BR9307225A (en) | 1999-05-11 |
AU5110693A (en) | 1994-05-09 |
CA2146661A1 (en) | 1994-04-28 |
EP0663917A1 (en) | 1995-07-26 |
JPH08505837A (en) | 1996-06-25 |
RU95113591A (en) | 1996-12-27 |
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