USRE39263E1 - Substituted aromatic thiocarboxylic acid amides and their use as herbicides - Google Patents
Substituted aromatic thiocarboxylic acid amides and their use as herbicides Download PDFInfo
- Publication number
- USRE39263E1 USRE39263E1 US10/735,572 US73557203A USRE39263E US RE39263 E1 USRE39263 E1 US RE39263E1 US 73557203 A US73557203 A US 73557203A US RE39263 E USRE39263 E US RE39263E
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- United States
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- alkyl
- diyl
- substituted
- formula
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- -1 aromatic thiocarboxylic acid Chemical class 0.000 title claims description 265
- 239000004009 herbicide Substances 0.000 title abstract description 6
- 239000000460 chlorine Chemical group 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 25
- 239000011737 fluorine Chemical group 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000005864 Sulphur Substances 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052794 bromium Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 10
- 125000006193 alkinyl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000004369 butenyl group Chemical class C(=CCC)* 0.000 claims description 3
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 3
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004368 propenyl group Chemical class C(=CC)* 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 0 [1*]C1=CC(C(N)=S)=C([2*])C([3*])=C1C Chemical compound [1*]C1=CC(C(N)=S)=C([2*])C([3*])=C1C 0.000 description 121
- 150000001875 compounds Chemical class 0.000 description 41
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VKHJBAVLOWCRNP-UHFFFAOYSA-N CN1N=C(C(F)(F)F)N(C)C1=O Chemical compound CN1N=C(C(F)(F)F)N(C)C1=O VKHJBAVLOWCRNP-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- NPJVLHHOGCGSIG-UHFFFAOYSA-N CN1C(=O)C=C(C(F)(F)F)N(C)C1=O Chemical compound CN1C(=O)C=C(C(F)(F)F)N(C)C1=O NPJVLHHOGCGSIG-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- IAZMRCDAEOWKHU-UHFFFAOYSA-N CN1N=C2CCCCC2=C1Cl Chemical compound CN1N=C2CCCCC2=C1Cl IAZMRCDAEOWKHU-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- BVKKBELLMAFEHT-UHFFFAOYSA-N CN1N=C2CCCCN2C1=O Chemical compound CN1N=C2CCCCN2C1=O BVKKBELLMAFEHT-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- KHQUVSTZLOTBMA-UHFFFAOYSA-N CCN1C(=O)N(C)N=C1C(F)(F)F Chemical compound CCN1C(=O)N(C)N=C1C(F)(F)F KHQUVSTZLOTBMA-UHFFFAOYSA-N 0.000 description 4
- 241000209510 Liliopsida Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 235000009973 maize Nutrition 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
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- 238000003786 synthesis reaction Methods 0.000 description 4
- ZMGMFSBQTDDNPX-UHFFFAOYSA-N 2,5-difluoro-4-[4-methyl-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-1-yl]benzonitrile Chemical compound O=C1N(C)C(C(F)(F)F)=NN1C1=CC(F)=C(C#N)C=C1F ZMGMFSBQTDDNPX-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- UCLIIUYLICFGDN-UHFFFAOYSA-N CN1N=C(C(F)F)N(C)C1=S Chemical compound CN1N=C(C(F)F)N(C)C1=S UCLIIUYLICFGDN-UHFFFAOYSA-N 0.000 description 3
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- 241001310793 Podium Species 0.000 description 3
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- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- 125000002950 monocyclic group Chemical group 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- 150000003558 thiocarbamic acid derivatives Chemical class 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
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical class CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 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
- 229930195735 unsaturated hydrocarbon Natural products 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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- C—CHEMISTRY; METALLURGY
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/44—Two oxygen atoms
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- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
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- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
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- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
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- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
Definitions
- the invention relates to novel substituted aromatic thiocarboxamides, to processes for their preparation and to their use as herbicides.
- chlorthiamid 2,6-dichloro-benzothioamide
- R 1 , R 2 , R 3 and Z have the meanings given above are reacted with hydrogen sulphide (H 2 S) or with thioacetamide, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.
- novel substituted aromatic thiocarboxamides of the general formula (I) are notable for strong and selective herbicidal activity.
- the saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkinyl—alone or in conjunction with heteroatoms, such as in alkoxy, alkylthio or alkylamino - are each straight-chain or branched.
- Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, especially fluorine or chlorine.
- the invention preferably relates to compounds of the formula (I) in which
- the invention particularly relates to compounds of the formula (I) in which
- radicals listed above apply both to the end products of the formula (I) and, correspondingly, to the repsective starting materials and intermediates required for preparation. These radical definitions can be combined as desired with one another, which therefore includes any desired combinations between the indicated ranges of preferred compounds.
- R 1 , R 2 and R 3 have the meanings indicated in the following list: Synthesis Ex. No. R 1 R 2 R 3 1 H F H 2 H Cl H 3 H Cl Cl 4 Cl F H 5 F F H 6 F F Cl 7 F CH 3 H 8 F C 2 H 5 H 9 F —CH 2 Cl H 10 F F F 11 F —NHC 2 H 5 H 12 F —CH 2 CN H 13 F —N(CH 3 )SO 2 C 2 H 5 H 14 Cl —N(CH 3 )SO 2 C 2 H 5 H 15 Cl —N(CH 3 )SO 2 C 2 H 5 Cl 16 F —NH—COCF 3 H 17 F —OH H 18 Cl —OH H 19 F —CH(CH 3 ) 2 H 20 F —NH—SO 2 —CH 3 H 21 F —SO 2 —CH 3 H 22 F —SO 2 —O—CH 3 H 23 F —SO 2 —NH—CH 3 H 24 F —COOCH 3 H 25 F —
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 2 and R 3 have, for example, the meanings indicated above in Group 1.
- R 1 , R 4 and R 5 have the meanings indicated in the following list:
- R 1 , R 4 and R 5 have, for example, the meanings indicated above in Group 85.
- Group 87
- R 1 , R 4 and R 5 have, for example, the meanings indicated above in Group 85.
- Group 88
- R 1 , R 4 and R 5 have, for example, the meanings indicated above in Group 85.
- Group 89
- R 1 , R 4 and R 5 have, for example, the meanings indicated above in Group 85.
- a general definition of the substituted aromatic nitriles to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I) is given by the formula (II).
- R 1 , R 2 , R 3 and Z preferably or in particular having those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as preferred or, respectively, as particularly preferred for R 1 , R 2 , R 3 and Z.
- the starting materials of the formula (II) are known and/or can be prepared by known processes (cf. EP-A 370332; DE-A 4238125; DE-A 4303376; U.S. Pat. No. 5,084,084; Preparation Examples).
- Suitable diluents for carrying out the process according to the invention are the customary organic solvents. These include, in particular, aliphatic, ahcyclic or aromatic, optionally halogenated hydrocarbons, for example benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetrachloromethane; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitrites, such as acetonitrile, propionitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide
- auxiliaries are all customary inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, for example sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium-tert-butylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tributylamine, N,N-methylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicycl
- reaction temperatures when carrying out the process according to the invention can be varied within a relatively large range. It is generally carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 80° C.
- the process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure, generally between 0.1 bar and 10 bar.
- the starting materials of the formula (II) are introduced, generally in a suitable diluent in the presence of a reaction auxiliary, and the hydrogen sulphide or the thioacetamide is slowly metered in.
- the hydrogen sulphide or the thioacetamide are preferably employed in a relatively large excess.
- the reaction mixture is stirred for a number of hours at the particular temperature required.
- Working up in the process according to the invention is effected in each case in accordance with customary methods (cf. the Preparation Examples).
- the active compounds according to the invention can be used as defoliants, desiccants, haulum killers and, especially, as weedkillers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends especially on the amount used.
- the active compounds according to the invention can be used, for example, in connection with the following plants:
- Monocotyledon crops of the genera Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
- the compounds are suitable for total weed control, for example on industrial terrain and rail tracks, and on paths and areas with or without tree stands.
- the compounds can be employed for controlling weeds in perennial crops, for example forests, ornamental 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, in lawns, turf and pastures, and for selective weed control in annual crops.
- the compounds of the formula (I) according to the invention are particularly suitable for selective control of monocotyledon and dioctyledon weeds in monocotyledon and dicotyledon crops, but pre- and post-emergence.
- the compounds of the formula (I) also show a fungicidal action, for example against Pyricularia oryzae in rice.
- the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dust, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric substances.
- formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
- organic solvents can, for example, also be used as auxiliary solvents.
- Liquid solvents which are mainly suitable are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic, hydrocarbons such as cyclohexane or paraffins, for example petroleum 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 and dimethyl sulphoxide, and water.
- Suitable solid carriers are:
- suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic metals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks;
- suitable emulsifiers and/or foam-formers are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates;
- Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives can be mineral and vegetable oils.
- colourants such as inorganic pigments, for example iron, oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, axo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- the formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
- the active compounds according to the invention can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
- herbicides examples being anilides, for example, diflufenican and propanil, arylcarboxylic acids, for example dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, for example 2,4 D, 2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr, aryloxy-phenoxy-alkanoic esters, for example diclofop(-methyl), fenoxaprop(-ethyl), fluazifop(-butyl), haloxyfop(-methyl) and quizalofop(-ethyl); azinones, for example chloridazon and norfluorazon; carabamates, for example chlorpropham, desmedipham, phenmaedipham and propham; chloroacetanildes, for example alachlor, acetochlor, butachlor, metazachlor, metalachlor, pret
- 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 already-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or spreading.
- 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 substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 10 g and 10 kg of active compound per hectare of soil surface, preferably between 50 g and 5 kg per ha
- Hydrogen sulphide is passed at from 50° C. to 60° C. to saturation point into a mixture of 5.5 g (15 mmol) of 2-(4-cyano-2-fluoro-5-ethylsulphonylamino-phenyl)-5,6,7,8-tetrahydro-1,2,4-triazole[4,3-a]pyridin-3-(2H)one, 5 ml of triethylamine and 50 ml of pyridine and the mixture is stirred at 60° C. for 30 minutes more. It is then concentrated in vacuo, the residue is stirred with 2 N hydrochloric acid and the solids are filtered off. The solid product is recrystallized from isopropanol.
- 0.3 g (10 mmol) of sodium hydride (80%) is added at from 0° C. to 5° C. to an initial charge of 1.8 g (10 mmol) of ethyl 3-amino-4,4,4-trifluoro-crotonate in 30 ml of dimethylformamide and 2 ml of toluene.
- the mixture is stirred at from 0° C. to 5° C. for 30 minutes.
- 0.9 g (5 mmol) of 4-cyano-2,5-difluorophenyl isocyanate—dissolved in 10 ml of toluene— is added and the mixture is stirred at from ⁇ 60° C.
- active compound 1 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 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.
- the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
- Emulsifier 1 part by weight of alkylaryl polyglycol ether
- active compound 1 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 have a height of 5-15 cm are sprayed with the preparation of active compound is such a way 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.
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Abstract
Description
This application is a divisional of application Ser. No. 08/732,257, filed on Oct. 28, 1996 (now U.S. Pat. No. 6,077,813), which is a 371 of PCT/EP95/01507, filed Apr. 21, 1995.
The invention relates to novel substituted aromatic thiocarboxamides, to processes for their preparation and to their use as herbicides.
It is already known that certain aromatic carbothioamides, for example 2,6-dichloro-benzothioamide (“chlorthiamid”), possess herbicidal properties (cf. GB-B 987253). However, the activity of this previously known compound, especially at low application rates and concentrations, is not entirely satisfactory in all areas of application.
The novel substituted aromatic thiocarboxamides have now been found of the general formula (I)
in which
in which
- R1 represents hydrogen or halogen,
- R2 represents the following group
—A1—A2—A3- in which
- A1 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N—A4—, in which A4 represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl,
- A1 additionally represents in each case optionally substituted alkanediyl, alkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl,
- A2 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N—A4—, in which A4 represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, aryl, alkoxy, alkylsulphonyl or arylsulphonyl,
- A2 additionally represents in each case optionally substituted alkanediyl, alkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or arenediyl,
- A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl, dialkoxy (thio)phosphoryl, alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino, alkinyloxycarbonyl, cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl, cycloalkylalkoxycarbonyl, aryl, aryloxy, arylalkyl, arylalkoxy, aryloxycarbonyl, arylalkoxycarbonyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkoxycarbonyl,
- R3 represents hydrogen or halogen or together with R2 represents an alkanediyl or an alkenediyl group which optionally contains at the beginning (or end) or within the hydrocarbon chain an oxygen atom, a sulphur atom, an SO2 group, an NH group, an N-alkyl group, a carbonyl group and/or a thiocarbonyl group, and
- Z represents in each case optionally substituted monocyclic or bicyclic, saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylimino.
The novel substituted aromatic thiocarboxamides of the general formula (I) are obtained if substituted aromatic nitrites of the general formula (II)
in which
in which
R1, R2, R3 and Z have the meanings given above are reacted with hydrogen sulphide (H2S) or with thioacetamide, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.
The novel substituted aromatic thiocarboxamides of the general formula (I) are notable for strong and selective herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl—alone or in conjunction with heteroatoms, such as in alkoxy, alkylthio or alkylamino - are each straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, especially fluorine or chlorine.
The invention preferably relates to compounds of the formula (I) in which
- R1 represents hydrogen, fluorine, chlorine or bromine,
- R2 represents the following group
—A1—A2—A3
in which- A1 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N—A4—, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl,
- A1 additionally represents in each case optionally fluorine- or chlorine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene,
- A2 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N—A4—, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl,
- A2 additionally represents in each case optionally fluorine- or chlorine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6cycloalkenediyl or phenylene,
- A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, or represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, akylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio) phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally halogen-substituted alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups, or represents in each case optionally halogen-, cyano-, carboxyl-, C1-C4-alkyl- and/or C1-C4-alkoxy-caronyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally nitro-, cyano-, carboxyl-, halogen-, C1-C4-alkyl-, C1-C4-halogenalkyl-, C1-C4-alkoxy-, C1-C4-halogenoalkyloxy- and/or C1-C4-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C1-C4-alkyl, phenyl-C1-C4-alkoxy, phenyloxycarbonyl or phenyl-C1-C4-alkoxycarbonyl, (in each case optionally totally or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1-C4-alkyl, furyl-C1-C4-alkyl, thienyl-C1-C4-alkyl, oxazolyl-C1-C4-alkyl isoxazole-C1-C4-alkyl, thiazole-C1-C4-alkyl, pyridinyl-C1-C4-alkyl, pyrimidinyl-C1-C4-alkyl, pyrazolylmethoxy or furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy,
- R3 represents hydrogen, fluorine, chlorine or bromine or together with R2 represents an alkanediyl or alkenediyl group having in each case up to 4 carbon atoms which optionally contains at the beginning (or end) or within the hydrocarbon chain an oxygen atom, a sulphur atom, an SO2 group, an NH group, an N—C1-C4-alkyl group, a carbonyl group and/or a thiocarbonyl group, and
- Z represents in each case monocyclic or bicyclic, saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylimino having in each case 2 to 6 carbon atoms and 1 to 4 nitrogen atoms in the heterocyclic ring system, which optionally additionally contains an oxygen atom or sulphur atom and/or optionally up to three groups from the series —CO—, —CS—, —SO— and/or SO2—, and which is optionally substituted by one or more groups from the series nitro, hydroxyl, amino, cyano, carboxyl, carbamoyl, thiocarbamaoyl, halogen, C3-C6-alkyl (which is optionally substituted by halogen or C1-C4-alkoxy), C2-C6-alkenyl or C2-C6-alkinyl (which are in each case optionally substituted by halogen), C1-C6-alkoxy or C1-C6-alkoxy-carbonyl (which are in each case optionally substituted by halogen or C1-C4-alkoxy), C2-C6-alkenyloxy or C2-C6-alkinyloxy (which are in each case optionally substituted by halogen), C1-C6-alkylthio, C2-C6-alkenylthio or C2-C6-alkinylthio (which are in each case optionally substituted by halogen), C1-C6-alkylamino or di-(C1-C4-alkyl)-amino, C3-C6-cycloalkyl or C3-C6-cycloalkyl-C1-C4-alkyl (which are in each case optionally substituted by halogen and/or C1-C4-alkyl), phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl or phenylamino (which are in each case optionally substituted by nitro, cyano, halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkyloxy, C1-C4-halogenoalkyloxy and/or C1-C4-alkoxycarbonyl).
The invention particularly relates to compounds of the formula (I) in which
- R1 represents hydrogen, fluorine or chlorine,
- R2 represents the following group
—A1—A2—A3
in which- A1 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N—A4—, in which A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-isopropyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl or ethylsulphonyl,
- A1 additionally represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2diyl, propine-1,2-diyl or 0propine-1,3-diyl,
- A2 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N—A4—, in which A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl or phenylsulphonyl,
- A2 additionally represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2diyl, propane-1,3diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl,
- A3 represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulpho, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, diethoxyphosphoryl, dipropoxyphosphoryl or diisopropoxyphosphoryl, or represents in each case optionally fluorine- or chlorine-substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, or represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxycarbonyl- or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexylideneamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, or represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl- and/or ethoxycarbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (in each case optionally completed or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolemethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethyl, furylmethoxy or pyridylmethoxy,
- R3 represents hydrogen, fluorine or chlorine or together with R2 represents an alkanediyl or alkenediyl group having in each case 1 to 3 carbon atoms which optionally contains at the beginning (or end) or within the hydrocarbon chain an oxygen atom, a sulphur atom, an NH group, an N-methyl group, a carbonyl group and/or a thiocarbonyl group, and
- Z represents in each case monocyclic or bicyclic, saturated or unsaturated heterocyclyl, heterocyclylamino or heterocyclylimino having in each case 2 to 5 carbon atoms and 1 to 3 nitrogen atoms in the heterocyclic ring system, which optionally additionally contains an oxygen atom or sulphur atom and/or optionally up to two groups from the series —CO—, —CS—, —SO— and/or SO2—, and which is optionally substituted by one or more groups from the series nitro, hydroxyl, amino, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine; methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, (which are optionally substituted by fluorine, chlorine, methoxy or ethoxy); propenyl, butenyl, propinyl or butinyl (which are in each case optionally substituted by fluorine or chlorine); methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl or ethoxycarbonyl (which are in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy); propenyloxy, butenyloxy, propinyloxy or butinyloxy (which are optionally substituted by fluorine or chlorine); methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, propenylthio, butenylthio, propinylthio or butinylthio (which are in each case optionally substituted by fluorine or chlorine); methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl (which are in each case optionally substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl), phenyl, phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl, or phenylamino (which are in each case optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl).
Very particularly preferred groups of compounds of the formula (I) are the compounds of the formula (Ia), (Ib) and (Ic) drawn below
- R1, R2 and Z have the meanings indicated above as particularly preferred,
- R4 and R5 are identical or different and independently of one another in each case individually represent hydrogen, fluorine, chlorine, methyl or ethyl—or in the formula (Ib) can also together represent oxygen or sulphur—and
- Q represents oxygen, sulphur, N-methyl or N-ethyl.
- Z in the general formulae (I) and ((Ia), (Ib) and (Ic) represents in particular the heterocyclic groups listed below
- where in each case
- Q1 represents a group from the series —CO—, —CS—, —CH2—, —CH(OH)—, —CHCl—, —CHBr—, —C(═CH2)—, —C(═CHF)—, —C(═CF2)—, —C(═CHCl)—, —C(═CHBr)—, —C(═CHOCHF3)—, —(═CHOCF3)—, —C(═CHOCH2CF3)—,
- Q2 represents oxygen, sulphur or a group from the series —CO—, —CS—, —CH2—, —CHF—, —CF2—, —CHCl—, —CHBr—, —CHOCHF2—, —CHOCF3—, —CHOCH2CF3—,
- R6 represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, methoxycarbonyl or ethoxycarbonyl, and
- R7 represents hydrogen, hydroxyl, amino, cyano, methyl, ethyl, n- or i-propyl, difluoromethyl, methoxy, ethoxy, n- or i-propoxy,
or where optionally two adjacent groups—R6 and R6 or R7 and R7 or R6 and R7—together represent in each case optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted alkanediyl or alkenediyl having in each case up to 4 carbon atoms which is optionally interrupted by oxygen, sulphur or a group from the series —SO—, SO2—, —N(CH3)— or N(C2H5)— at the beginning (or at the end) or within the hydrocarbon chain.
The definitions of radicals listed above, indicated in general or in ranges of preference, apply both to the end products of the formula (I) and, correspondingly, to the repsective starting materials and intermediates required for preparation. These radical definitions can be combined as desired with one another, which therefore includes any desired combinations between the indicated ranges of preferred compounds.
Examples of the compounds of the formula (I) according to the invention are listed in the groups below.
Group 1
(IA-1) | |
|
In this formula, |
R1, R2 and R3 have the meanings indicated in the following list: |
Synthesis | |||
Ex. No. | R1 | R2 | R3 |
1 | H | F | H |
2 | H | Cl | H |
3 | H | Cl | Cl |
4 | Cl | F | H |
5 | F | F | H |
6 | F | F | Cl |
7 | F | CH3 | H |
8 | F | C2H5 | H |
9 | F | —CH2Cl | H |
10 | F | F | F |
11 | F | —NHC2H5 | H |
12 | F | —CH2CN | H |
13 | F | —N(CH3)SO2C2H5 | H |
14 | Cl | —N(CH3)SO2C2H5 | H |
15 | Cl | —N(CH3)SO2C2H5 | Cl |
16 | F | —NH—COCF3 | H |
17 | F | —OH | H |
18 | Cl | —OH | H |
19 | F | —CH(CH3)2 | H |
20 | F | —NH—SO2—CH3 | H |
21 | F | —SO2—CH3 | H |
22 | F | —SO2—O—CH3 | H |
23 | F | —SO2—NH—CH3 | H |
24 | F | —COOCH3 | H |
25 | F | —CO—NH—CH3 | H |
26 | Cl | —COOCH3 | Cl |
27 | Cl | —COOC2H5 | H |
28 | F | —O—C2H5 | H |
29 | F | —N(C2H5)SO2C2H5 | H |
30 | F | —N(SO2CH3)2 | H |
31 | F | —CO—N(CH3)2 | H |
32 | F | —S—CH2—C≡CH | H |
33 | Cl | —S—CH2C═CH | F |
34 | F | —S—CH2—CH≡CH | Cl |
35 | F | —O—CH(CH3)—C≡CH | H |
36 | F | —S—CH2—COOCH3 | H |
37 | F | —O—CH2CH2—OCH3 | H |
38 | F | —O(CH2CH2O)2CH3 | H |
39 | F | —O—CH2—CH═CH2 | H |
40 | F | —O—CH2—C≡CH | H |
41 | F | —SH | H |
42 | F | —S—CH2 | H |
43 | F | —S—C2H5 | H |
44 | F | —S—CH(CH3)2 | H |
45 | F | —O—CH2—CF3 | H |
46 | F | —O—CH(CH2F)2 | H |
47 | F | | H |
48 | F | | H |
49 | F | —NH—SO2C2H5 | H |
50 | Cl | —NH—SO2C2H5 | H |
51 | F | —NH—SO2C2H5 | Cl |
52 | F | —NH—SO2CH(CH3)2 | H |
53 | F | —NH—SO2C4H9 | H |
54 | F | —N═CH—OC2H5 | H |
55 | F | —N═C(CH3)OC2H5 | H |
56 | F | —N═C(OCH3)2 | H |
57 | F | —N═CH—N(CH3)2 | H |
58 | F | —SCN | H |
59 | F | —SO2Cl | H |
60 | F | —O—CS—N(CH3)2 | H |
61 | F | —S—CO—N(CH3)2 | H |
62 | F | —NH—P(O)(CH3)OC2H5 | H |
63 | F | —NH—P(O)(OC2H5)2 | H |
64 | F | —NH—COC2H5 | H |
65 | F | —N(CH3)COCF3 | H |
66 | F | —NH—COCH(CH3)2 | H |
67 | F | —NH—CO—CO—C(CH3)3 | H |
68 | F | —NH—CO—NH2 | H |
69 | F | —NH—CO—NHCH3 | H |
70 | F | —NH—CO—N(CH3)2 | H |
71 | F | —N(COCH3)2 | H |
72 | F | —NH—COCH(CH2)Cl | H |
73 | F | —S—CH2—CH═CH2 | H |
74 | Cl | —S—CH2—CH═CH2 | H |
75 | F | —S—CH(CH3)C≡CH | H |
76 | F | —S—CH(CH3)COOC2H5 | H |
77 | F | —S(O)—CH3 | H |
78 | F | | H |
79 | F | | H |
80 | F | | H |
81 | F | | H |
82 | F | | H |
83 | F | | H |
84 | F | —O—CH2—CN | H |
85 | F | —O—SO2CH3 | H |
86 | F | —OCH2—CH(Cl)═CH2 | H |
87 | F | —O—CH2—COOCH3 | H |
88 | F | —O—CHF2 | H |
89 | F | —OCOOCH2CH2Cl | H |
90 | F | —OCH2P(O)(OC2H5)2 | H |
91 | Cl | —O—CH(CH3)P(O)(OC2H5)2 | H |
92 | F | | H |
93 | F | | H |
94 | F | —O—N(C2H5)2 | H |
95 | F | | H |
96 | F | | H |
97 | F | | Cl |
98 | Cl | | H |
99 | F | | F |
100 | F | | H |
101 | F | | H |
102 | F | | H |
103 | F | —NCH(CH3)2SO2C2H5 | H |
104 | F | —N(CH3)SO2CH(CH3)2 | H |
105 | H | —N(CH3)SO2C2H5 | Cl |
106 | Cl | —N(CH3)SO2C4H9 | H |
107 | F | —N(CH3)SO2C2H5 | H |
108 | F | —N(CH3)SO2CH3 | H |
109 | F | —N(SO2C2H5)2 | H |
110 | F | —N(SO2CH3)SO2C2H5 | H |
111 | F | | H |
112 | F | —N(CH3)2 | H |
113 | F | —NH2 | H |
114 | Cl | —NH2 | H |
115 | Cl | —O—CH(CH3)2 | H |
116 | F | —O—CH(CH3)2 | H |
117 | F | | H |
118 | Cl | | H |
119 | F | —O—CH2—COOC2H5 | H |
120 | F | —S—CH2—COOCH3 | H |
121 | F | —S—CH2—COOC2H5 | H |
122 | Cl | —S—CH2—COOC2H5 | H |
123 | F | —CH2—CH(Cl)COOCH3 | H |
124 | F | —CH2—CH(Cl)COOC2H5 | H |
125 | F | —CH2—CH(Cl)CONHC2H5 | H |
126 | Cl | —CH2—CH(Cl)CONHC2H5 | H |
127 | Cl | | H |
128 | F | | H |
129 | F | —COOC3H7-i | H |
Group 2
In this formula, R1, R4 and R5 have the meanings indicated in the following list:
In this formula, R1, R4 and R5 have, for example, the meanings indicated above in Group 85.
Group 87
Group 87
In this formula, R1, R4 and R5 have, for example, the meanings indicated above in Group 85.
Group 88
Group 88
In this formula, R1, R4 and R5 have, for example, the meanings indicated above in Group 85.
Group 89
Group 89
In this formula, R1, R4 and R5 have, for example, the meanings indicated above in Group 85.
Using, for example, 2-(2-fluoro-4-cyano-5-methoxyphenyl)-4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one and hydrogen sulphide as starting materials, the course of reaction of the process according to the invention can be illustrated by the following equation:
A general definition of the substituted aromatic nitriles to be used as starting materials in the process according to the invention for the preparation of the compounds of the general formula (I) is given by the formula (II). In the formula (II), R1, R2, R3 and Z preferably or in particular having those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as preferred or, respectively, as particularly preferred for R1, R2, R3 and Z.
The starting materials of the formula (II) are known and/or can be prepared by known processes (cf. EP-A 370332; DE-A 4238125; DE-A 4303376; U.S. Pat. No. 5,084,084; Preparation Examples).
Suitable diluents for carrying out the process according to the invention are the customary organic solvents. These include, in particular, aliphatic, ahcyclic or aromatic, optionally halogenated hydrocarbons, for example benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetrachloromethane; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitrites, 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, sulphoxides, such as dimethyl sulphoxide, azines, such as pyridine, alcohols, such as methanol, ethanol n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water, or pure water.
The process according to the invention is preferably carried out in the presence of a suitable reaction auxiliary. Suitable such auxiliaries are all customary inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, for example sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium-tert-butylate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate and also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tributylamine, N,N-methylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
The reaction temperatures when carrying out the process according to the invention can be varied within a relatively large range. It is generally carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 80° C.
The process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure, generally between 0.1 bar and 10 bar.
To carry out the process according to the invention the starting materials of the formula (II) are introduced, generally in a suitable diluent in the presence of a reaction auxiliary, and the hydrogen sulphide or the thioacetamide is slowly metered in. The hydrogen sulphide or the thioacetamide are preferably employed in a relatively large excess. The reaction mixture is stirred for a number of hours at the particular temperature required. Working up in the process according to the invention is effected in each case in accordance with customary methods (cf. the Preparation Examples). The active compounds according to the invention can be used as defoliants, desiccants, haulum killers and, especially, as weedkillers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends especially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, 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, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotyledon crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanium, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledon weeds of the genera: Echinochloa, Setaris, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrosis, Alopecurus and Apera.
Monocotyledon crops 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.
Depending on the concentration, the compounds are suitable for total weed control, for example on industrial terrain and rail tracks, and on paths and areas with or without tree stands. Equally, the compounds can be employed for controlling weeds in perennial crops, for example forests, ornamental 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, in lawns, turf and pastures, and for selective weed control in annual crops.
The compounds of the formula (I) according to the invention are particularly suitable for selective control of monocotyledon and dioctyledon weeds in monocotyledon and dicotyledon crops, but pre- and post-emergence.
To a certain extent, the compounds of the formula (I) also show a fungicidal action, for example against Pyricularia oryzae in rice.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dust, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic, hydrocarbons such as cyclohexane or paraffins, for example petroleum 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 and dimethyl sulphoxide, and water.
Suitable solid carriers are:
for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montinorillonite 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, or else synthetic granules of inorganic and organic metals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-formers are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates; suitable dispersants 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 latexes such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colourants such as inorganic pigments, for example iron, oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, axo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Possible components for the mixtures are known herbicides, examples being anilides, for example, diflufenican and propanil, arylcarboxylic acids, for example dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, for example 2,4 D, 2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr, aryloxy-phenoxy-alkanoic esters, for example diclofop(-methyl), fenoxaprop(-ethyl), fluazifop(-butyl), haloxyfop(-methyl) and quizalofop(-ethyl); azinones, for example chloridazon and norfluorazon; carabamates, for example chlorpropham, desmedipham, phenmaedipham and propham; chloroacetanildes, for example alachlor, acetochlor, butachlor, metazachlor, metalachlor, pretilachlor and propachlor; dinitroanilines, for example oryzalin, pendimethalin and trifluralin; diphenyl ethers, for example aciffuorfen, bifenox, chlormethoxynil (X-52), chlornitrofen, fluoroglycofen, fomesafen, halosafen, lactofen, nitrofen and oxyfluorfen; ureas, for example chlortoluron, cumyluron (JC-940), diuron, dymron (daimuron), fluormeturon, isoproturon, linuron and methabenzathiazuron; hyroxylamines, for example alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, for example imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, for example bromoxynil, dichlorobenil and ioxynil; oxyacetamides, for example mefenacet; sulphonylureas, for example AC-014 (AC-322140), amidosulfuron, bensulfonuron(-methyl), chlorimuron(-ethyl), chlorsulfuron, cinosulfuron, DPX-47, HOE-404, imazosulfuron, metasulfuron(-methyl), nicosulfuron, primisulfuron, pyrazosulfuron(-ethyl), thifensulfouron(-methyl), triasulfuron and tribenuron(-methyl); thiocarbamates, for example butylate, cycloate, diallate, dimepiperate, EPTC, esprocarb, molinate, prosulphocarb, thiobencarb (benthiocarb) and triallate; triazines, for example atrazine, cyanazine, dimethametyn, promeltryne, simazin, simetryne, terbutryne and terbutylazin; triazinones, for example hexazinon, metamitron and metribuzin; others, for example aminotriazole, benfuresale, bensulide, bentazone, benzofenap, bromobutide, butamifos, cafenstrole (CH-900), cinmethylin, clomazone, clomeprop, clopyralid, DEH-112, difenzoquat, dimethenamid, dithiopyr, ethofumesate, flumetsulam, fluorochloridone, glufosinate, glyphosate; aminoprophos(-methyl), anilofos, etobenzamid (HW-52), isoxaben, KPP-314, KUH-833, KUH-911, KUH-920, MK-243, naproanilide, KSK-850, oxadiazon, piperophos, propanil, pyrazolate, pyrazoxyfen, pyributicarb, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.
Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil conditioners, are 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 already-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or spreading.
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 substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 10 g and 10 kg of active compound per hectare of soil surface, preferably between 50 g and 5 kg per ha
The preparation and use of the active compounds according to the invention can be seen from the examples which follow.
Hydrogen sulphide is passed at from 50° C. to 60° C. to saturation point into a mixture of 5.5 g (15 mmol) of 2-(4-cyano-2-fluoro-5-ethylsulphonylamino-phenyl)-5,6,7,8-tetrahydro-1,2,4-triazole[4,3-a]pyridin-3-(2H)one, 5 ml of triethylamine and 50 ml of pyridine and the mixture is stirred at 60° C. for 30 minutes more. It is then concentrated in vacuo, the residue is stirred with 2 N hydrochloric acid and the solids are filtered off. The solid product is recrystallized from isopropanol.
4.8 g (80% of theory) of 2-2-fluoro-5-ethylsulphonylamino-4-thiocarbamoyl-phenyl)-5,6,7,8-tetrahydro-1,2,4triazolo[4,3-a]pyridin-3(2H)-one are obtained of melting point 220° C.
4.04 g (0.04 mol) of triethylamine are added to 6.3 g (0.02 mol) of 2-(2-fluoro-4-cyano-5-amino-phenyl)-4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 100 ml of acetone. Hydrogen sulphide is passed in rapidly at 23° C., and the internal temperature rises to 33° C. The reaction is complete after 1 hour. The solution is concentrated on a rotary evaporator and the residue is recrystallized from isopropanol.
2.9 g (42% theory) of 2-(4-fluoro-4-thiocarbamoyl-5-amino-phenyl)-4-ethyl-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained of melting point 161° C.
11 g (0.0276 mol) of 2-(2-fluoro-4-cyano-5-ethylsulphonylaminophenyl)-4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazole-3-thione are stirred at 70° C. for 4.5 hours in 100 ml of pyridine while passing in hydrogen sulphide. The solution is concentrated on a rotary evaporator, the residue is stirred in water, the mixture is acidified with concentrated hydrochloric acid, and precipitated product is filtered off, washed with water and recrystallized from isopropanol.
9 g (77% of theory) of 2-(2-fluoro-4-thiocarbamoyl-5-ethylsulphonylaminophenyl)-4-methyl-5-difluoromethyl-2,4dihydro-3H-1,2,4-triazole-3-thione are obtained of melting point 183° C.
In analogy to Preparation Examples 1, 2 and 3 and in accordance with the general description of the preparation process according to the invention it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below.
TABLE 1 |
Examples of the compounds of the formula (I) |
(I) | |
|
Melting | |||||
Ex. No. | R1 | R2 | R3 | Z | point (° C.) |
4 | F | F | H | | 110 |
5 | F | —NH—SO2—C2H5 | H | | 143 |
6 | F | | H | | 162 |
7 | F | —NH—SO2—C2H5 | H | | 237 (Triethyl- ammonium salt) |
8 | F | F | H | | 220 |
9 | F | —NH—SO2—C2H5 | H | | 218 |
10 | F | —NH—SO2—C2H5 | H | | 185 |
11 | F | F | H | | 218 |
12 | F | —OC2H5 | H | | 202 |
13 | F | —NH—SO2—C2H5 | H | | 210 |
14 | F | —NH—SO2—C2H5 | H | | 203 |
15 | F | F | H | | 185 |
16 | F | | H | | 170 |
17 | F | —OCH(CH3)2 | H | | 206 |
18 | F | OH | H | | 250 |
19 | F | | H | | 98 |
20 | F | —NH—SO2—C2H5 | H | | 208 |
21 | F | —NH—SO2—C2H5 | H | | 53 |
22 | F | —NH—SO2—C2H5 | H | | (amorphous) |
23 | F | —NH—SO2—C2H5 | H | | 183 |
24 | F | | H | | 167 |
25 | F | —NH—SO2—CH3 | H | | 130 |
26 | F | —NH—SO2—CH3 | H | | 243 |
27 | F | F | H | | 199 |
28 | F | —NH—SO2—C2H5 | H | | 202 |
29 | F | —NH—SO2—CH3 | H | | 200 |
30 | F | —NH—SO2—CH(CH3)2 | H | | 204 |
31 | F | —NH—SO2—C2H5 | H | | 195 |
32 | F | | H | | 122 |
33 | F | —O—CH2—C≡CN | H | | 190 |
34 | F | —NH—SO2—CH3 | H | | 178 |
35 | F | —NH—SO2—C3H7 | H | | 203 |
36 | F | —NH—SO2—C2H5 | H | | 199 |
37 | F | —NH—SO2—C2H5 | H | | 153 |
38 | F | —NH—SO2—C2H5 | H | | 206 |
39 | F | —NH—SO2—C2H5 | H | | 167 |
40 | F | F | H | | 130 |
41 | F | —OCH2CF3 | H | | 173 |
42 | F | —OC2H4OCH3 | H | | 148 |
43 | F | —OC2H5 | H | | 155 |
44 | F | —OC3H7 | H | | 130 |
45 | F | F | H | | 131 |
46 | F | —OCH(CH3)2 | H | | 202 |
47 | F | —OC2H5 | H | | 185 |
48 | F | —NH—SO2—C2H5 | H | | 111 |
49 | H | —NH—SO2—C2H5 | H | | 118 |
50 | F | —NH—SO2—C3H7−n | H | | 143 |
51 | F | —OC2H4OC2H4OCH3 | H | | 168 |
52 | F | —NH—SO2—C3H7−n | H | | (amorphous) |
53 | F | —NH—SO2—C3H7−n | H | | 232 |
54 | F | —NH—SO2—C3H7−i | H | | 226 |
55 | F | —NH—SO2—C3H7−i | H | | 187 |
56 | F | —NH—SO2—C3H7−i | H | | 236 |
57 | F | —NH—SO2—C3H7−i | H | | 252 |
58 | F | —NH—SO2—C3H7−i | H | | 109 |
59 | F | —NH—SO2—C3H7−i | H | | 207 |
60 | F | —NH—SO2—C3H7−i | H | | 215 |
61 | F | —N(CH3)—SO2C2H5 | H | | 102 |
62 | F | —NH—SO2—C2H5 | H | | 185 |
63 | Cl | —NH—SO2—C2H5 | H | | 121 |
64 | F | F | H | | 157 |
65 | F | —NH—SO2—C2H5 | H | | 195 |
66 | F | —OH | H | | 193 (decomp) DBU salt |
Preparation of the Starting Compounds:
5.8 g (0.042 mol) of potassium carbonate are added at room temperature to 6.3 g (0.034 mol) of 4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one (cf. e.g. U.S. Pat. No. 3,780,052) and 5.4 g (0.034 mol) of 2,3,5-trifluorobenzoidtrile (cf. e.g. EP 191181) in 150 ml of dimethyl sulphoxide and the mixture is subsequently heated at 100° C. for 14 hours. For working up, the cooled reaction mixture is placed in water, adjusted to a pH of 2 with dilute hydrochloric acid and subjected several times to extraction with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed over silica gel (eluent: dichloromethane).
6.2 g (60% of theory) of 1-(4-cyano-2,5-difluorophenyl)-4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one are obtained of melting point 74° C.
0.83 g (0.006 mmol) of potassium carbonate is added at room temperature to 1.52 g (0.005 mol) of 1-(4-cyano-2,5-difluorophenyl)-4-methyl-3-trifluoromethyl-1,2,4-triazolin-5-one and 0.48 g (0.005 mol) of methanesulphonamide in 50 ml of dimethyl sulphoxide and the mixture is subsequently heated at 120° C. for 12 hours. For working up, the cooled reaction mixture is placed in water, adjusted to a pH of 2 with dilute hydrochloric acid and subjected several times to extraction with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated in vacuo. The residue is chromatographed over silica gel (eluent: dichloromethane/methanol 20:1).
0.55 g (28% of theory) of 1-(4-cyano-2-fluoro-5-methylsulphonylaminophenyl)-4-methyl-3-trifluoromethyl-1,2,4triazole-5-one is obtained of melting point 67° C.
0.3 g (10 mmol) of sodium hydride (80%) is added at from 0° C. to 5° C. to an initial charge of 1.8 g (10 mmol) of ethyl 3-amino-4,4,4-trifluoro-crotonate in 30 ml of dimethylformamide and 2 ml of toluene. The mixture is stirred at from 0° C. to 5° C. for 30 minutes. After the mixture has been cooled to −70° C., 0.9 g (5 mmol) of 4-cyano-2,5-difluorophenyl isocyanate—dissolved in 10 ml of toluene—is added and the mixture is stirred at from −60° C. to −70° C. for 150 minutes. After the cooling bath has been removed, 2 ml of acetic acid are added. The mixture is then diluted with water to about twice the volume and subjected to extraction with ethyl acetate. The organic phase is concentrated and the residue is crystallized with diisopropyl ether.
1.1 g (69% of theory) of 1-(4-cyano-2,5-difluoro-phenyl)-3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1-(2H)-pyrimidine are obtained of melting point 194° C.
A mixture of 0.83 g (3 mmol) of 1-(4-cyano-2,5-difluorophenyl)-3,6-dihydro-2,6-dioxo-3,4-dimethyl-(2H)-pyrimidine, 0.32 g (3 mmol) of methane sulphonamide, 0.6 g of potassium carbonate and 10 m of dimethyl sulphoxide is heated at 120° C. for 10 hours. After cooling, the mixture is poured into ice-water and acidified with 2 N hydrochloric acid. It is then subjected to extraction with ethyl acetate and the organic phase is washed with water, dried with sodium sulphate and filtered. The solvent is carefully removed from the filtrate by distillation under a water-pump vacuum.
0.8 g (76% of theory) of 1-(4-cyano-2-fluoro-5-methylsulphonylmainophenyl)-3,6-dihydro-2,6-dioxo-3,4-dimethyl-1(2H)-pyrimidine is obtained as crystalline residue (melting point>250° C.).
Use Examples:
Pre-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, 1 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 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
TABLE A |
Pre-emergence test/greenhouse |
Active | ||||||||
compound | Applica- | |||||||
(Synthesis | tion | |||||||
Example | rate | Amaran- | Cheno- | Matri- | Portu- | Sola- | ||
Number) | (g/ha) | Barley | Maize | thus | podium | caria | laca | num |
(3) | 125 | 0 | 0 | 100 | 100 | 100 | 100 | 100 |
(5) | 125 | 0 | 0 | 100 | 100 | 90 | 90 | 100 |
(6) | 125 | 0 | 30 | 100 | 100 | 95 | 100 | 100 |
(7) | 125 | 30 | 0 | 100 | 100 | 95 | 100 | 95 |
TABLE B |
Pre-emergence test/greenhouse |
Active | |||||||||
compound | Applica- | ||||||||
(Synthesis | tion | ||||||||
Example | rate | Abu- | Amaran- | Cheno- | Matri- | Portu- | Sola- | ||
Number) | (g/ha) | Wheat | Maize | thilon | thus | podium | caria | laca | num |
19 | 60 | 10 | 0 | 100 | 95 | 100 | 100 | 100 | 100 |
20 | 60 | 20 | 0 | 100 | 100 | 100 | 100 | 100 | 100 |
21 | 60 | 0 | 0 | 100 | 100 | 100 | 100 | 100 | 100 |
22 | 250 | 0 | 20 | 100 | 100 | 100 | 100 | 95 | 100 |
23 | 60 | 0 | 0 | 95 | 70 | 95 | 100 | 95 | 70 |
24 | 30 | 0 | 20 | 100 | 95 | 100 | 100 | 100 | 100 |
25 | 30 | 0 | 0 | 100 | 100 | 90 | 100 | 100 | 100 |
26 | 60 | 0 | 0 | 100 | 80 | 100 | 100 | 100 | 90 |
4 | 250 | 0 | 10 | 80 | 50 | 70 | 95 | 90 | 70 |
5 | 125 | 0 | 0 | 10 | 100 | 100 | 70 | 90 | 100 |
3 | 60 | 0 | 0 | 100 | 100 | 100 | 100 | 100 | 100 |
6 | 60 | 20 | 30 | 100 | 100 | 100 | 100 | 100 | 95 |
7 | 125 | 50 | 0 | 95 | 100 | 100 | 95 | 100 | 95 |
8 | 60 | 40 | 0 | 100 | 100 | 100 | 95 | 95 | 100 |
9 | 60 | 0 | 0 | 100 | 100 | 100 | 95 | 90 | 100 |
1 | 125 | 0 | 0 | 100 | 100 | 100 | 95 | 100 | 100 |
12 | 60 | 20 | 0 | 70 | 70 | 100 | 95 | 95 | 70 |
13 | 60 | 0 | 0 | 100 | 100 | 100 | 70 | 90 | 100 |
16 | 60 | 10 | 0 | 95 | 20 | 100 | 90 | 80 | 80 |
17 | 30 | 0 | 0 | 100 | 100 | 100 | 100 | 100 | 100 |
28 | 60 | 0 | 20 | 100 | 100 | 100 | 100 | 100 | 100 |
29 | 60 | 0 | 0 | 100 | 100 | 100 | 100 | 100 | 100 |
30 | 60 | 0 | 0 | 100 | 100 | 100 | 90 | 100 | 100 |
31 | 60 | 0 | 0 | 100 | 100 | 100 | 100 | 100 | 100 |
32 | 30 | 10 | 0 | — | 100 | 100 | 100 | 95 | 100 |
33 | 30 | 10 | 10 | 95 | 95 | 100 | 100 | 100 | 100 |
34 | 60 | 0 | 0 | 100 | 100 | 100 | 100 | 100 | 100 |
35 | 60 | 0 | 0 | 100 | 100 | 100 | 90 | 95 | 100 |
40 | 250 | 20 | 0 | 30 | 40 | 100 | 95 | 100 | 80 |
41 | 60 | 20 | 30 | 100 | 100 | 100 | 100 | 100 | 100 |
45 | 125 | 0 | 0 | 95 | 100 | 100 | 100 | 90 | 95 |
46 | 60 | 0 | 70 | 100 | 100 | 100 | 100 | 100 | 100 |
47 | 30 | 0 | 0 | 100 | 95 | 100 | 100 | 100 | 100 |
48 | 60 | 0 | 0 | 100 | 100 | 100 | 100 | 100 | 100 |
51 | 30 | 0 | 20 | 100 | — | 100 | 95 | 100 | 100 |
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, 1 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 have a height of 5-15 cm are sprayed with the preparation of active compound is such a way 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 (like untreated condition)
- 100%=total destruction
TABLE C |
Post-emergence test/greenhouse |
Active | ||||||||
compound | Applica- | |||||||
(Synthesis | tion | |||||||
Example | rate | Abu- | Amaran- | Cheno- | Sola- | Veron- | ||
Number) | (g/ha) | Wheat | Maize | thilon | thus | podium | num | ica |
19 | 4 | 5 | 20 | 95 | 95 | 95 | 100 | 100 |
20 | 4 | 0 | 15 | 100 | 95 | 95 | 100 | 95 |
21 | 4 | 5 | 60 | 90 | 100 | 70 | 100 | 100 |
22 | 30 | 15 | 0 | 100 | 100 | 40 | 100 | 20 |
23 | 30 | 0 | 50 | 95 | — | 90 | 100 | 100 |
24 | 30 | 15 | 70 | 100 | 100 | 100 | 100 | 100 |
25 | 15 | 0 | 50 | 100 | 100 | 100 | 100 | 100 |
26 | 15 | 0 | 30 | 50 | 90 | 50 | 50 | 100 |
5 | 15 | 10 | 20 | 100 | 100 | 100 | 100 | 100 |
3 | 30 | 10 | 30 | 100 | 100 | 100 | 100 | 100 |
6 | 8 | 30 | 50 | 100 | 100 | 100 | 100 | 95 |
7 | 60 | 10 | 50 | 100 | 100 | 95 | 100 | 95 |
8 | 60 | 10 | 30 | 100 | 100 | 100 | 100 | 100 |
9 | 60 | 10 | 30 | 100 | 100 | 100 | 100 | 100 |
1 | 15 | 10 | 50 | 100 | 95 | 95 | 100 | 100 |
12 | 8 | 10 | 30 | 100 | 100 | 95 | 100 | 100 |
13 | 15 | 0 | 30 | 95 | 100 | 80 | 100 | 90 |
16 | 60 | 20 | 60 | 95 | 100 | 100 | 100 | 100 |
17 | 8 | 10 | 10 | 100 | 100 | 95 | 100 | 100 |
28 | 30 | 0 | 30 | 100 | 100 | 90 | 100 | 100 |
29 | 8 | 5 | 0 | 70 | 100 | 90 | 100 | 95 |
30 | 8 | 0 | 50 | 100 | 100 | 95 | 100 | 70 |
31 | 8 | 0 | 70 | 100 | 100 | 90 | 100 | 100 |
32 | 4 | 15 | 30 | 100 | 100 | 95 | 100 | 100 |
33 | 4 | 20 | 60 | 100 | 100 | 100 | 100 | 100 |
34 | 15 | 0 | 30 | 100 | 100 | 100 | 100 | 100 |
35 | 30 | 0 | 25 | 100 | 100 | 90 | 100 | 95 |
40 | 125 | 10 | 5 | 50 | 70 | 100 | 100 | 90 |
41 | 15 | 20 | 50 | 100 | 80 | 90 | 100 | 95 |
43 | 15 | 0 | 50 | 100 | 95 | 100 | 100 | 100 |
44 | 8 | 0 | 15 | 100 | 100 | 100 | 95 | 100 |
45 | 8 | 10 | 40 | 95 | 95 | 95 | 100 | — |
46 | 8 | 15 | 20 | 100 | 100 | 95 | 100 | 100 |
47 | 8 | 10 | 10 | 100 | 100 | 95 | 100 | 100 |
48 | 8 | 5 | 60 | 100 | 100 | 80 | 100 | 100 |
49 | 8 | 0 | 60 | 60 | 100 | 10 | 100 | 100 |
50 | 15 | 5 | 70 | 100 | 95 | 80 | 100 | 95 |
51 | 15 | 15 | 60 | 100 | 100 | 70 | 100 | 100 |
Claims (7)
wherein
R1 represents hydrogen, fluorine, chlorine or bromine,
R2 represents the following group
—A1—A2—A3
—A1—A2—A3
in which
A1 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N(A4)—, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl,
A1 additionally represents in each case optionally fluorine- or chlorine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene,
A2 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N—(A4)—, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl,
A2 additionally represents in each case optionally fluorine- or chlorine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6cycloalkenediyl or phenylene,
A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, or represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, akylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio) phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally halogen-substituted alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups, or represents in each case optionally halogen-, cyano-, carboxyl-, C1-C4-alkyl- and/or C1-C4-alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally nitro-, cyano-, carboxyl-, halogen-, C1-C4-alkyl-, C1-C4-halogenalkyl-, C1-C4-alkoxy-, C1-C4-halogenoalkyloxy- and/or C1-C4-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C1-C4-alkyl, phenyl-C1-C4-alkoxy, phenyloxycarbonyl or phenyl-C1-C4-alkoxycarbonyl, (in each case optionally totally or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1-C4-alkyl, furyl-C1-C4-alkyl, thienyl-C1-C4-alkyl, oxazolyl-C1-C4-alkyl isoxazole-C1-C4-alkyl, thiazole-C1-C4-alkyl, pyridinyl-C1-C4-alkyl, pyrimidinyl-C1-C4-alkyl, pyrazolylmethoxy or furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy,
R3 represents hydrogen, fluorine, chlorine or bromine or together with R2 represents an alkanediyl or alkenediyl group having in each case up to 4 carbon atoms which optionally contains at the beginning (or end) or within the hydrocarbon chain an oxygen atom, a sulphur atom, an SO2 group, an NH group, an N—C1-C4-alkyl group, a carbonyl group and/or a thiocarbonyl group, and
wherein:
Q1 represents a group from the series —CO—, —CS—, —CH2—, —CH(OH)—, —CHCl—, —CHBr—, —C(═CH2)—, —C(═CHF)—, —C(═CF2)—, —C(═CHCl)—, —C(═CHBr)—, —C(═CHOCHF3)—, —C (═CHOCF3)—, —C(═CHOCH2CF3)—,
R6 represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoro-methoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, methoxycarbonyl or ethoxycarbonyl, and
R7 represents hydrogen, hydroxyl, amino, cyano, methyl, ethyl, n- or i-propyl, difluoromethyl, methoxy, ethoxy, n- or i-propoxy.
wherein
R1 represents hydrogen, fluorine, chlorine or bromine,
R2 represents the following group
—A1—A2—A3
—A1—A2—A3
in which
A1 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N(A4)—, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl,
A1 additionally represents in each case optionally fluorine- or chlorine-substituted C1-C6-alkendiyl, C2-C6-alkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene,
A2 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N(A4)—, in which A4 represents hydrogen, hydroxyl, C1-C4-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C4-alkoxy, phenyl, C1-C4-alkylsulphonyl or phenylsulphonyl,
A2 additionally represents in each case optionally fluorine- or chlorine-substituted C1-C6-alkanediyl, C2-C6-alkenediyl, C2-C6-alkinediyl, C3-C6-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene,
A3 represents hydrogen, hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen, or represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents in each case optionally halogen-substituted alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl having in each case 2 to 6 carbon atoms in the alkenyl, alkylidene or alkinyl groups, or represents in each case optionally halogen-, cyano-, carboxyl-, C1-C4-alkyl- and/or C1-C4-alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or represents in each case optionally nitro-, cyano-, carboxyl-, halogen, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkyloxy-, C1-C4-halogenoalkyloxy- and/or C1-C4-alkoxy-carbonyl-substituted phenyl, phenyloxy, phenyl-C1-C4-alkyl, phenyl-C1-C4-alkoxy, phenyloxycarbonyl or phenyl-C1-C4-alkoxycarbonyl, (in each case optionally totally or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C1-C4-alkyl, furyl-C1-C4-alkyl, thienyl-C1-C4-alkyl, oxazolyl-C1-C4-alkyl, isoxazole-C1-C4-alkyl, thiazole-C1-C4-alkyl, pyridinyl-C1-C4-alkyl, pyrimidinyl-C1-C4-alkyl, pyrazolylmethoxy or furylmethoxy, or represents perhydropyranylmethoxy or pyridylmethoxy,
R3 represents hydrogen, fluorine, chlorine or bromine or together with R2 represents an alkanediyl or alkenediyl group having in each case up to 4 carbon atoms which optionally contains at the beginning (or end) or within the hydrocarbon chain an oxygen atom, a sulphur atom, an SO2 group, an NH group, an N—C1-C4-alkyl group, a carbonyl group and/or thiocarbonyl group, and
wherein
Q1 represents a group from the series —CO—, —CS—, —CH2—, —CH(OH)—, —CHCl—, —CHBr—, —C(═CH2)—, —C(═CHF)—, —C(═CF2)—, —C(═CHCl)—, —C(═CHBr)—, —C(═CHOCHF2)—, —C(═CHOCF3)—, —C(═CHOCH2CF3)—,
R6 represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoro-methoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, methoxycarbonyl or ethoxycarbonyl, and
R7 represents hydrogen, hydroxyl, amino, cyano, methyl, ethyl, n- or i-propyl, difluoromethyl, methoxy, ethoxy, n- or i-propoxy.
3. A substituted aromatic thiocarboxamide of the formula (I) according to claim 2 , wherein
R1 represents hydrogen, fluorine, or chlorine,
R2 represents the following group
—A1—A2—A3
—A1—A2—A3
in which
A1 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N(A4)—, in which A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl or ethylsulphonyl,
A1 additionally represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl,
A2 represents a single bond, or represents oxygen, sulphur, —SO—, —SO2—, —CO— or the group —N(A4)—, in which A4 represents hydrogen, hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl or phenylsulphonyl,
A2 additionally represents methylene, ethane-1,1-diyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1,2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethine-1,2-diyl, propine-1,2-diyl or propine-1,3-diyl,
A3 represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulpho, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-bytyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s-, or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxy-phosphoryl, diethoxyphosphoryl, dipropoxy-phosphoryl or diisopropoxyphosphoryl, or represents in each case optionally fluorine- or chlorine-substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino, butinylamino, propinyloxycarbonyl or butinyloxycarbonyl, or represents in each case optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, ethyl-, n- or i-propyl-, methoxycarbonyl- or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylideneamino, cyclohexylideneamino, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, pr represents in each case optionally nitro-, cyano-, carboxyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, thifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl- and/or ethoxycarbonyl-substituted phenyl, phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (in each case optionally completely or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolemethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazlylmethoxy, furylmethoxy or pyridylmethoxy, and
R3 represents hydrogen, fluorine or chlorine or together with R2 represents an alkanediyl or alkenediyl group having in each case 1 to 3 carbon atoms which optionally contains at the beginning (or end) or within the hydrocarbon chain an oxygen atom, a sulphur atom, an NH group, an N-methyl group, a carbonyl group and/or a thiocarbonyl group.
in which R1, R2, R3 and Z have the meanings given in claim 2 , comprising reacting a substituted aromatic nitrile of the formula (II)
in which
R1, R2, R3 and Z have the meanings indicated above, with hydrogen sulphide (H2S) or with thioacetamide, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.
5. A method of combatting unwanted plants comprising applying to said plants and/or heir habitat a herbicidally effective amount of at least one substituted aromatic thiocarboxamide of the formula (I) according to claim 1 or 2 .
6. A herbicidal composition comprising a herbicidally effective amount of at least one substituted aromatic thiocarboxamide of the formula (I) according to claim 2 or 3 and at least one extender and/or surfactant.
7. A method of combatting unwanted plants comprising applying to said plants and/or their habitat a herbicidally effective amount of at least one substituted aromatic thiocarboxamide of the formula (I) according to claim 2 or 3 .
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US08/732,257 US6077813A (en) | 1994-05-04 | 1995-04-21 | Substituted aromatic thiocarboxylic acid amides and their use as herbicides |
PCT/EP1995/001507 WO1995030661A1 (en) | 1994-05-04 | 1995-04-21 | Substituted aromatic thiocarboxylic acid amides and their use as herbicides |
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