SK495090A3 - Sulfonylaminocarbonyltriazolinones, method for their preparation, herbicidal agents them containing, and their use their use - Google Patents

Sulfonylaminocarbonyltriazolinones, method for their preparation, herbicidal agents them containing, and their use their use Download PDF

Info

Publication number: SK495090A3
Authority: SK; Slovakia
Prior art keywords: chlorine; fluorine; group; alkoxy; alkyl
Prior art date: 1989-10-12

Application number

SK4950-90A

Other languages

English (en)

Slovak (sk)

Other versions

SK280209B6 (sk

Inventor

Klaus-Helmut Muller

Peter Babczinski

Hans-Joachim Santel

Robert R Schmidt

Original Assignee

Bayer Ag

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

1989-10-12

Filing date

1990-10-11

Publication date

1999-09-10

1990-10-11 Application filed by Bayer Ag filed Critical Bayer Ag

1999-09-10 Publication of SK280209B6 publication Critical patent/SK280209B6/sk

1999-09-10 Publication of SK495090A3 publication Critical patent/SK495090A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 48
238000002360 preparation method Methods 0.000 title claims abstract description 18
PRZRAMLXTKZUHF-UHFFFAOYSA-N 5-oxo-n-sulfonyl-4h-triazole-1-carboxamide Chemical class O=S(=O)=NC(=O)N1N=NCC1=O PRZRAMLXTKZUHF-UHFFFAOYSA-N 0.000 title claims description 8
239000004009 herbicide Substances 0.000 title abstract description 7
-1 mercapto, amino Chemical group 0.000 claims abstract description 66
150000001875 compounds Chemical class 0.000 claims abstract description 56
125000000217 alkyl group Chemical group 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
239000001257 hydrogen Substances 0.000 claims abstract description 29
125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 23
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 7
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
239000000460 chlorine Substances 0.000 claims description 135
229910052801 chlorine Inorganic materials 0.000 claims description 119
229910052731 fluorine Inorganic materials 0.000 claims description 119
239000011737 fluorine Substances 0.000 claims description 105
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 97
125000001153 fluoro group Chemical group F* 0.000 claims description 82
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 59
229910052794 bromium Inorganic materials 0.000 claims description 57
125000004432 carbon atom Chemical group C* 0.000 claims description 54
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 53
125000004093 cyano group Chemical group *C#N 0.000 claims description 48
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 42
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 34
239000002904 solvent Substances 0.000 claims description 34
241000196324 Embryophyta Species 0.000 claims description 33
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 25
125000001309 chloro group Chemical group Cl* 0.000 claims description 24
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
239000004480 active ingredient Substances 0.000 claims description 22
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 19
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 11
239000011230 binding agent Substances 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 7
230000002363 herbicidal effect Effects 0.000 claims description 7
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 5
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000005108 alkenylthio group Chemical group 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims description 2
125000005109 alkynylthio group Chemical group 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
125000005265 dialkylamine group Chemical group 0.000 claims description 2
125000005879 dioxolanyl group Chemical group 0.000 claims description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
125000004428 fluoroalkoxy group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
125000005493 quinolyl group Chemical group 0.000 claims description 2
125000002769 thiazolinyl group Chemical group 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
WNWOTMKHOLCHRJ-UHFFFAOYSA-N 1,4-dihydrotriazol-5-one Chemical class O=C1CN=NN1 WNWOTMKHOLCHRJ-UHFFFAOYSA-N 0.000 claims 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
QASSGBYGCRXJMF-UHFFFAOYSA-N n-sulfonyl-4,5-dihydrotriazole-1-carboxamide Chemical class O=S(=O)=NC(=O)N1CCN=N1 QASSGBYGCRXJMF-UHFFFAOYSA-N 0.000 claims 1
230000008635 plant growth Effects 0.000 claims 1
125000003118 aryl group Chemical group 0.000 abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 abstract description 4
XBZOKYAFLSKAHA-UHFFFAOYSA-N 3-oxo-n-sulfonyl-1h-1,2,4-triazole-2-carboxamide Chemical class O=S(=O)=NC(=O)N1NC=NC1=O XBZOKYAFLSKAHA-UHFFFAOYSA-N 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
125000001072 heteroaryl group Chemical group 0.000 abstract 1
238000002844 melting Methods 0.000 description 59
230000008018 melting Effects 0.000 description 59
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
239000007858 starting material Substances 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
238000012360 testing method Methods 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
150000002431 hydrogen Chemical class 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
239000003995 emulsifying agent Substances 0.000 description 11
239000000126 substance Substances 0.000 description 10
241000209094 Oryza Species 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
230000000694 effects Effects 0.000 description 8
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 7
241000207763 Solanum Species 0.000 description 7
235000002634 Solanum Nutrition 0.000 description 7
239000000243 solution Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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235000007164 Oryza sativa Nutrition 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
244000062793 Sorghum vulgare Species 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
235000009566 rice Nutrition 0.000 description 6
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241000208296 Datura Species 0.000 description 5
241000748465 Galinsoga Species 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
241001330975 Magnaporthe oryzae Species 0.000 description 5
241000220261 Sinapis Species 0.000 description 5
239000013543 active substance Substances 0.000 description 5
125000001246 bromo group Chemical group Br* 0.000 description 5
230000006378 damage Effects 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
244000075850 Avena orientalis Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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235000011684 Sorghum saccharatum Nutrition 0.000 description 4
125000002877 alkyl aryl group Chemical group 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical class O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
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238000010992 reflux Methods 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
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239000000969 carrier Substances 0.000 description 3
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IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
150000002429 hydrazines Chemical class 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
230000009885 systemic effect Effects 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
PHBNVKLHBGBNLT-UHFFFAOYSA-N 1-ethoxy-3-(propanoylamino)urea Chemical compound CCONC(=O)NNC(=O)CC PHBNVKLHBGBNLT-UHFFFAOYSA-N 0.000 description 2
YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 2
239000002794 2,4-DB Substances 0.000 description 2
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MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 2
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ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
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QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
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IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- 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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Pest Control & Pesticides (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK4950-90A 1989-10-12 1990-10-11 Sulfonylaminocarbonyltriazolinones, method for their preparation, herbicidal agents them containing, and their use their use SK495090A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3934081A DE3934081A1 (de)	1989-10-12	1989-10-12	Sulfonylaminocarbonyltriazolinone

Publications (2)

Publication Number	Publication Date
SK280209B6 SK280209B6 (sk)	1999-09-10
SK495090A3 true SK495090A3 (en)	1999-09-10

Family

ID=6391328

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK4950-90A SK495090A3 (en)	1989-10-12	1990-10-11	Sulfonylaminocarbonyltriazolinones, method for their preparation, herbicidal agents them containing, and their use their use

Country Status (13)

Country	Link
EP (2)	EP0683157B1 (fr)
JP (1)	JPH03133966A (fr)
KR (1)	KR0171400B1 (fr)
AU (1)	AU627080B2 (fr)
BR (1)	BR9005095A (fr)
CA (4)	CA2302058C (fr)
CZ (1)	CZ281525B6 (fr)
DE (3)	DE3934081A1 (fr)
DK (2)	DK0683157T3 (fr)
ES (2)	ES2087107T3 (fr)
HU (1)	HU218976B (fr)
PL (1)	PL165494B1 (fr)
SK (1)	SK495090A3 (fr)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
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DE3936622A1 (de) *	1989-11-03	1991-05-08	Bayer Ag	Halogenierte sulfonylaminocarbonyltriazolinone
DE4110795A1 (de) *	1991-04-04	1992-10-08	Bayer Ag	Sulfonylaminocarbonyltriazolinone mit ueber sauerstoff gebundenen substituenten
DE4131842A1 (de) *	1991-09-25	1993-04-01	Bayer Ag	Sulfonylaminocarbonyltriazolinone mit zwei ueber sauerstoff gebundenen substituenten
DE4030063A1 (de) *	1990-09-22	1992-03-26	Bayer Ag	Substituierte 5-alkoxy-1,2,4,-triazol-3-(thi)one
US6906006B1 (en)	1988-11-23	2005-06-14	Bayer Aktiengesellschaft	N-arly-substituted nitrogen-containing heterocycles, processes and novel intermediates for their preparation, and their use as herbicides and plant growth regulators
DE4238125A1 (de) *	1992-11-12	1994-05-19	Bayer Ag	Substituierte Triazolinone
DE3928662A1 (de) *	1989-08-30	1991-03-07	Bayer Ag	Substituierte 4,5-diamino-1,2,4-triazol-3-(thi)one
US5534486A (en) *	1991-04-04	1996-07-09	Bayer Aktiengesellschaft	Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen
DE4316430A1 (de) *	1993-05-17	1994-11-24	Bayer Ag	Substituierte Triazolinone
DE4343595A1 (de) *	1993-12-21	1995-06-22	Bayer Ag	Verfahren zur Herstellung von Sulfonylaminocarbonyltriazolinonen
DE4411913A1 (de) *	1994-04-07	1995-10-12	Bayer Ag	Substituierte Sulfonylaminocarbonyltriazolinone
DE4435547A1 (de) *	1994-10-05	1996-04-11	Bayer Ag	Sulfonylaminocarbonyltriazolinone mit über Sauerstoff und Schwefel gebundenen Substituenten
DE19502579A1 (de) *	1995-01-27	1996-08-01	Bayer Ag	Sulfonylamino(thio)carbonyl-triazolin(thi)one
DE19525974A1 (de) *	1995-07-17	1997-01-23	Bayer Ag	Substituierte Arylsulfonylamino(thio)carbonyltriazolin(thi)one
DE19530450A1 (de) *	1995-08-18	1997-02-20	Bayer Ag	Verfahren zur Herstellung von substituierten Aminotriazolinonen
ZA974703B (en) *	1996-05-30	1997-12-30	Bayer Ag	Substituted sulfonylamino(thio)carbonyl compounds.
DE19632945A1 (de) *	1996-08-16	1998-02-19	Bayer Ag	Substituierte Sulfonylamino(thio)carbonylverbindungen
DE19802697A1 (de)	1998-01-24	1999-07-29	Bayer Ag	Selektive Herbizide auf Basis von N-Aryl-triazolin(thi)onen und N-Arylsulfonylamino(thio)carbonyltriazolin(thi)onen
DE19823131A1 (de) *	1998-05-23	1999-11-25	Bayer Ag	Sulfonylamino(thio)carbonyltriazolin(thi)one mit Alkenyl-Substituenten
DE19843766A1 (de) *	1998-09-24	2000-03-30	Bayer Ag	Substituierte Thiazol(in)ylidenaminosulfonylamino(thio)carbonyl-triazolinone
DE19845408A1 (de) *	1998-10-02	2000-04-27	Bayer Ag	Selektive Herbizide auf Basis eines substituierten Phenylsulfonylaminocarbonyl-triazolinons
DE19845407B4 (de) *	1998-10-02	2012-06-28	Arysta LifeScience North America Corp.(n.d.Ges.d.Staates Californien)	Selektive Herbizide auf Basis eines substituierten Phenylsulfonylaminocarbonyl-triazolinons
US5912354A (en) *	1998-12-11	1999-06-15	Bayer Corporation	Process for preparing 4-amino-1,2,4-triazolin-5-ones
KR100704718B1 (ko) *	1999-12-27	2007-04-09	바이엘 코포레이션	설포닐아미노카보닐 트리아졸리논 염의 제조방법
KR100431154B1 (ko) *	2002-04-12	2004-05-12	(주)하나실업	데님제품의 무늬 성형방법
EP1717228A1 (fr)	2005-04-28	2006-11-02	Bayer CropScience GmbH	Dérivés de sulfonylamino(thio)carbonyl comme herbicides et regulateurs de la croissance végétale
DE102008060967A1 (de)	2008-12-06	2010-06-10	Bayer Schering Pharma Aktiengesellschaft	Substituierte Phenylsulfonyltriazolone und ihre Verwendung
WO2013134562A1 (fr)	2012-03-09	2013-09-12	Inception 2, Inc.	Composés de triazolone et leurs utilisations
AU2013363398B2 (en)	2012-12-20	2017-06-01	Tempest Therapeutics, Inc.	Triazolone compounds and uses thereof
BR112015031291A2 (pt)	2013-06-20	2017-07-25	Bayer Cropscience Ag	derivados de sulfureto de arila e derivados de arilalquil sulfóxido como acaricidas e inseticidas
US9776976B2 (en)	2013-09-06	2017-10-03	Inception 2, Inc.	Triazolone compounds and uses thereof
JOP20190094A1 (ar)	2016-10-27	2019-04-25	Broad Inst Inc	مركبات 1، 2، 4-تريازولون تحمل ثلاثة بدائل عند المواقع 2، 4، 5 مفيدة كمثبطات لديهيدروجيناز ثنائي هيدرو أوروتات (dhodh)

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Publication number	Priority date	Publication date	Assignee	Title
DE1126882B (de) *	1960-05-03	1962-04-05	Boehringer Sohn Ingelheim	Verfahren zur Herstellung von 1,2,4-Triazolonen-(5)
US4487773A (en) *	1981-03-16	1984-12-11	Mead Johnson & Company	1,2,4-Triazol-3-one antidepressants
BE894856A (fr) *	1982-10-28	1983-02-14	Fahlberg List Veb	Compositions herbicides a base d'un derive de la 1,2,4-triazolinone-(5)
US4575555A (en) *	1983-06-29	1986-03-11	Mead Johnson & Company	4-(3-Chlorophenyl)-1,2,3,6-tetrahydropyridine derivative
DE3709574A1 (de) *	1987-03-24	1988-10-06	Bayer Ag	Substituierte triazolinone
DE3815765A1 (de) *	1988-05-09	1989-11-23	Bayer Ag	2-sulfonylaminocarbonyl-2,4-dihydro-3h-1,2,4- triazol-3-one einschliesslich 4,5-kondensierter, bicyclischer derivate, verfahren und neue zwischenprodukte zu ihrer herstellung und ihre verwendung als pflanzenbehandlungsmittel
EP0332133B1 (fr) *	1988-03-07	1994-08-24	Chugai Seiyaku Kabushiki Kaisha	Dérivés du triazole, procédé pour leur préparation et compositions herbicides les contenant

1989
- 1989-10-12 DE DE3934081A patent/DE3934081A1/de not_active Withdrawn
1990
- 1990-09-29 DK DK95111736T patent/DK0683157T3/da active
- 1990-09-29 DE DE59010314T patent/DE59010314D1/de not_active Expired - Lifetime
- 1990-09-29 DK DK90118750.0T patent/DK0422469T3/da active
- 1990-09-29 DE DE59010938T patent/DE59010938D1/de not_active Expired - Lifetime
- 1990-09-29 ES ES90118750T patent/ES2087107T3/es not_active Expired - Lifetime
- 1990-09-29 EP EP95111736A patent/EP0683157B1/fr not_active Expired - Lifetime
- 1990-09-29 ES ES95111736T patent/ES2222457T3/es not_active Expired - Lifetime
- 1990-09-29 EP EP90118750A patent/EP0422469B1/fr not_active Expired - Lifetime
- 1990-10-09 JP JP2269742A patent/JPH03133966A/ja active Pending
- 1990-10-10 CA CA002302058A patent/CA2302058C/fr not_active Expired - Lifetime
- 1990-10-10 CA CA002189698A patent/CA2189698C/fr not_active Expired - Lifetime
- 1990-10-10 CA CA002420329A patent/CA2420329C/fr not_active Expired - Lifetime
- 1990-10-10 PL PL90287259A patent/PL165494B1/pl unknown
- 1990-10-10 CA CA002027206A patent/CA2027206C/fr not_active Expired - Lifetime
- 1990-10-11 CZ CS904950A patent/CZ281525B6/cs not_active IP Right Cessation
- 1990-10-11 AU AU64591/90A patent/AU627080B2/en not_active Expired
- 1990-10-11 BR BR909005095A patent/BR9005095A/pt not_active IP Right Cessation
- 1990-10-11 SK SK4950-90A patent/SK495090A3/sk not_active IP Right Cessation
- 1990-10-11 HU HU419/90A patent/HU218976B/hu unknown
- 1990-10-11 KR KR1019900016081A patent/KR0171400B1/ko not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2302058C (fr)	2004-05-25
EP0422469A2 (fr)	1991-04-17
CA2189698C (fr)	2003-05-06
CA2189698A1 (fr)	1991-04-13
BR9005095A (pt)	1991-09-17
JPH03133966A (ja)	1991-06-07
EP0683157B1 (fr)	2004-05-26
DE59010938D1 (de)	2004-07-01
AU6459190A (en)	1991-04-18
EP0422469A3 (en)	1992-01-08
KR0171400B1 (ko)	1999-02-01
KR910007893A (ko)	1991-05-30
HU906419D0 (en)	1991-04-29
AU627080B2 (en)	1992-08-13
ES2222457T3 (es)	2005-02-01
DE59010314D1 (de)	1996-06-13
CA2420329A1 (fr)	1991-04-13
PL165494B1 (pl)	1994-12-30
CA2027206C (fr)	1997-12-23
EP0422469B1 (fr)	1996-05-08
CZ495090A3 (en)	1996-07-17
CZ281525B6 (cs)	1996-10-16
ES2087107T3 (es)	1996-07-16
HU218976B (hu)	2001-01-29
HUT55369A (en)	1991-05-28
SK280209B6 (sk)	1999-09-10
DK0422469T3 (da)	1996-08-26
PL287259A1 (en)	1992-01-27
CA2420329C (fr)	2005-11-29
DK0683157T3 (da)	2004-09-27
DE3934081A1 (de)	1991-04-18
CA2302058A1 (fr)	1991-04-13
EP0683157A1 (fr)	1995-11-22
CA2027206A1 (fr)	1991-04-13

Legal Events

Date	Code	Title	Description
2010-12-07	MK4A	Expiry of patent	Expiry date: 20101011

Publication	Publication Date	Title
SK495090A3 (en)	1999-09-10	Sulfonylaminocarbonyltriazolinones, method for their preparation, herbicidal agents them containing, and their use their use
AU623284B2 (en)	1992-05-07	Halogenated sulphonylaminocarbonyltriazolinones
US5234897A (en)	1993-08-10	Herbicidal 3-amino-5-aminocarbonyl-1,2,4-triazoles
CA2398159C (fr)	2006-05-30	Sulfonylaminocarbonyltriazolinones renfermant des substituants lies par l'oxygene
KR970011282B1 (ko)	1997-07-09	설포닐아미노카보닐트리아졸리논
US4952235A (en)	1990-08-28	(Hetero)aryloxynaphthalenes having substituents bonded via sulphur
EP0431291B1 (fr)	1998-07-29	Sulfonylaminocarbonyl-triazolinones comportant des substituants attachés par du soufre
SK400788A3 (en)	1999-02-11	Substituted triazolinones, method and intermediate products for manufacturing thereof, their use and herbicidal agent containing same
US5256632A (en)	1993-10-26	Herbicidal sulphonylated carboxamides
US5061310A (en)	1991-10-29	Herbicidal n-phenyl-substituted oxazinediones and oxazinonethiones
US5205853A (en)	1993-04-27	Herbicidal sulphonylated carboxamides
CA2051894C (fr)	1999-07-13	Derives de substitution de 5-alcoxy-1,2,4-triazol-3-(thi)ones
US4981507A (en)	1991-01-01	Herbicidal triazoloazines
US5129944A (en)	1992-07-14	Herbicidal aryloxynaphthalene derivatives
US5006156A (en)	1991-04-09	Herbicidal sulfonylaminoazines
US5217522A (en)	1993-06-08	Herbicidal sulphonylguanidinoazines
US5234899A (en)	1993-08-10	Substituted 2,2-difluoro-1,3-benzodioxyl-4-ketone herbicides
DE3905006A1 (de)	1990-08-30	N-aryl-stickstoffheterocyclen mit fluorhaltigen substituenten
US4960455A (en)	1990-10-02	Herbicidal triazolodihydropyrimidine-2-sulphonamides
US5328896A (en)	1994-07-12	Preparing herbicidal sulphonylurea salts
CA2032398A1 (fr)	1991-06-20	Procede de preparation de sels de sulfonyluree, nouveaux sels de sulfonyluree et leur utilisation comme herbicides
JPH04243868A (ja)	1992-08-31	アクリロフエノン化合物及びその製法
CA2037136A1 (fr)	1991-09-02	Pyrimidinecarboxamides sulfonyles