KR20150003784A - Ｎ-(테트라졸-5-일)- 및 ｎ-(트리아졸-5-일)아릴카복사미드 염 및 제초제로서의 그의 용도 - Google Patents
Ｎ-(테트라졸-5-일)- 및 ｎ-(트리아졸-5-일)아릴카복사미드 염 및 제초제로서의 그의 용도 Download PDFInfo
- Publication number
- KR20150003784A KR20150003784A KR20147030768A KR20147030768A KR20150003784A KR 20150003784 A KR20150003784 A KR 20150003784A KR 20147030768 A KR20147030768 A KR 20147030768A KR 20147030768 A KR20147030768 A KR 20147030768A KR 20150003784 A KR20150003784 A KR 20150003784A
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- KR
- South Korea
- Prior art keywords
- alkyl
- halo
- cycloalkyl
- heterocyclyl
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 239000004009 herbicide Substances 0.000 title claims abstract description 21
- 150000003839 salts Chemical class 0.000 title claims abstract description 13
- -1 triazol-5-yl Chemical group 0.000 claims abstract description 168
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 58
- 150000002367 halogens Chemical class 0.000 claims abstract description 57
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- 150000001768 cations Chemical class 0.000 claims abstract description 11
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 350
- 125000005843 halogen group Chemical group 0.000 claims description 102
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 80
- 150000003254 radicals Chemical class 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 70
- 125000000623 heterocyclic group Chemical group 0.000 claims description 66
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004043 oxo group Chemical group O=* 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 30
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 30
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 28
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
- 230000002363 herbicidal effect Effects 0.000 claims description 19
- 230000009261 transgenic effect Effects 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 238000009472 formulation Methods 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 150000002500 ions Chemical class 0.000 claims description 13
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000000417 fungicide Substances 0.000 claims description 5
- 244000045561 useful plants Species 0.000 claims description 5
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 4
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 4
- XQFGVGNRDPFKFJ-UHFFFAOYSA-N 1,2,3,5,6,7-hexahydropyrrolo[1,2-b]pyridazine Chemical compound N1CCC=C2CCCN21 XQFGVGNRDPFKFJ-UHFFFAOYSA-N 0.000 claims description 4
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 claims description 4
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2,5-dimethylpyridine Chemical compound CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 4
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 230000000895 acaricidal effect Effects 0.000 claims description 3
- 239000000642 acaricide Substances 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000003974 emollient agent Substances 0.000 claims description 3
- 239000003630 growth substance Substances 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 2
- HCUOEKSZWPGJIM-IYNMRSRQSA-N (e,2z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 claims description 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910001424 calcium ion Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910001416 lithium ion Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910001425 magnesium ion Inorganic materials 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 2
- 229910001414 potassium ion Inorganic materials 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
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- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229930000044 secondary metabolite Natural products 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- 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
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
-
- 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
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12166621 | 2012-05-03 | ||
| EP12166621.8 | 2012-05-03 | ||
| PCT/EP2013/058964 WO2013164331A1 (de) | 2012-05-03 | 2013-04-30 | Salze von n-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamiden und ihre verwendung als herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150003784A true KR20150003784A (ko) | 2015-01-09 |
Family
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Family Applications (1)
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| KR20147030768A Ceased KR20150003784A (ko) | 2012-05-03 | 2013-04-30 | Ｎ-(테트라졸-5-일)- 및 ｎ-(트리아졸-5-일)아릴카복사미드 염 및 제초제로서의 그의 용도 |
Country Status (19)
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| US (1) | US9371315B2 (OSRAM) |
| EP (2) | EP3121172B1 (OSRAM) |
| JP (1) | JP6104368B2 (OSRAM) |
| KR (1) | KR20150003784A (OSRAM) |
| CN (1) | CN104271563B (OSRAM) |
| AR (1) | AR090939A1 (OSRAM) |
| AU (1) | AU2013255929B2 (OSRAM) |
| BR (1) | BR112014027185B1 (OSRAM) |
| CA (1) | CA2872374A1 (OSRAM) |
| CO (1) | CO7180218A2 (OSRAM) |
| EA (1) | EA025517B1 (OSRAM) |
| ES (1) | ES2705618T3 (OSRAM) |
| HU (1) | HUE042768T2 (OSRAM) |
| IN (1) | IN2014DN08150A (OSRAM) |
| MX (1) | MX363987B (OSRAM) |
| PL (1) | PL3121172T3 (OSRAM) |
| UA (1) | UA113545C2 (OSRAM) |
| WO (1) | WO2013164331A1 (OSRAM) |
| ZA (1) | ZA201408836B (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170129205A (ko) * | 2015-03-17 | 2017-11-24 | 바이엘 크롭사이언스 악티엔게젤샤프트 | N-(1,3,4-옥사디아졸-2-일)아릴 카복실산 아미드의 염 및 제초제로서의 그의 용도 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2014184074A1 (en) * | 2013-05-15 | 2014-11-20 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)hetarylcarboxamide compounds and their use as herbicides |
| KR20160015211A (ko) | 2013-05-31 | 2016-02-12 | 닛산 가가쿠 고교 가부시키 가이샤 | 복소환 아미드 화합물 |
| CN106414741A (zh) | 2013-11-28 | 2017-02-15 | 拜耳作物科学股份公司 | 2-氯-3-(甲基硫烷基)-n-(1-甲基-1h-四唑-5-基)-4-(三氟甲基)苯甲酰胺或其盐在耐受hppd抑制剂除草剂的转基因作物植物的区域中防治不想要的植物的用途 |
| WO2015177063A1 (en) * | 2014-05-19 | 2015-11-26 | Syngenta Participations Ag | Insecticidally active amide derivatives with sulfur-substituted phenyl or pyridine groups |
| PL3160946T3 (pl) * | 2014-06-30 | 2018-08-31 | Bayer Cropscience Aktiengesellschaft | Skuteczne chwastobójczo amidy kwasu benzoesowego |
| AR100918A1 (es) * | 2014-06-30 | 2016-11-09 | Bayer Cropscience Ag | Amidas de ácido arilcarboxílico con actividad herbicida |
| WO2017042259A1 (en) | 2015-09-11 | 2017-03-16 | Bayer Cropscience Aktiengesellschaft | Hppd variants and methods of use |
| WO2018114663A1 (de) | 2016-12-22 | 2018-06-28 | Bayer Cropscience Aktiengesellschaft | Substituierte azolylpyrrolone und azolylhydantoine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| US20190367457A1 (en) | 2016-12-30 | 2019-12-05 | Mitobridge, Inc. | Oxopyridine derivatives useful as aminocarboxymuconate semialdehyde decarboxylase (acmsd) inhibitors |
| US11180770B2 (en) | 2017-03-07 | 2021-11-23 | BASF Agricultural Solutions Seed US LLC | HPPD variants and methods of use |
| WO2018202535A1 (de) * | 2017-05-04 | 2018-11-08 | Bayer Cropscience Aktiengesellschaft | Herbizid wirksame 4-difluormethylbenzoylamide |
| TW202128652A (zh) * | 2019-10-21 | 2021-08-01 | 韓國化學研究院 | 菸鹼醯胺化合物以及包含彼等之除草劑組成 |
| CN115884967A (zh) * | 2020-04-07 | 2023-03-31 | 拜耳公司 | 取代的间苯二酸二酰胺 |
| WO2024074126A1 (zh) * | 2022-10-05 | 2024-04-11 | 江苏中旗科技股份有限公司 | 一种4-甲磺酰基苯甲酰胺类化合物、制备方法、除草组合物及用途 |
| KR20250091222A (ko) * | 2022-10-05 | 2025-06-20 | 지앙수 플래그 케미컬 인더스트리 컴퍼니 리미티드 | 4-메틸설포닐벤즈아미드류 화합물, 제조방법, 제초 조성물 및 용도 |
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| MA19269A1 (fr) * | 1980-09-16 | 1982-04-01 | Lilly Co Eli | Perfectionnement relatif a des derives de n-arylbenzamides . |
| WO1984002919A1 (en) | 1983-01-17 | 1984-08-02 | Monsanto Co | Plasmids for transforming plant cells |
| BR8404834A (pt) | 1983-09-26 | 1985-08-13 | Agrigenetics Res Ass | Metodo para modificar geneticamente uma celula vegetal |
| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| ATE80182T1 (de) | 1985-10-25 | 1992-09-15 | Monsanto Co | Pflanzenvektoren. |
| DE3765449D1 (de) | 1986-03-11 | 1990-11-15 | Plant Genetic Systems Nv | Durch gentechnologie erhaltene und gegen glutaminsynthetase-inhibitoren resistente pflanzenzellen. |
| EP0305398B1 (en) | 1986-05-01 | 1991-09-25 | Honeywell Inc. | Multiple integrated circuit interconnection arrangement |
| US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| IL83348A (en) | 1986-08-26 | 1995-12-08 | Du Pont | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| DE3733017A1 (de) | 1987-09-30 | 1989-04-13 | Bayer Ag | Stilbensynthase-gen |
| EP0472722B1 (en) | 1990-03-16 | 2003-05-21 | Calgene LLC | Dnas encoding plant desaturases and their uses |
| RU2148081C1 (ru) | 1990-06-18 | 2000-04-27 | Монсанто Компани | Способ получения генетически трансформированных растений с повышенным содержанием крахмала и рекомбинантная двухцепочечная днк-молекула |
| DE69132939T2 (de) | 1990-06-25 | 2002-11-14 | Monsanto Technology Llc | Glyphosattolerante pflanzen |
| DE4107396A1 (de) | 1990-06-29 | 1992-01-02 | Bayer Ag | Stilbensynthase-gene aus weinrebe |
| SE467358B (sv) | 1990-12-21 | 1992-07-06 | Amylogene Hb | Genteknisk foeraendring av potatis foer bildning av staerkelse av amylopektintyp |
| DE4104782B4 (de) | 1991-02-13 | 2006-05-11 | Bayer Cropscience Gmbh | Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide |
| CN1548425A (zh) | 2003-05-13 | 2004-11-24 | 拜尔农作物科学股份公司 | 取代的三唑甲酰胺 |
| CN103282354B (zh) * | 2010-09-01 | 2016-05-04 | 拜耳知识产权有限责任公司 | N-(四唑-5-基)-和n-(三唑-5-基)芳基甲酰胺及其作为除草剂的用途 |
| EP2739611B1 (de) | 2011-08-03 | 2015-05-13 | Bayer Intellectual Property GmbH | N-(tetrazol-5-yl)- und n-(triazol-5-yl)arylcarbonsäureamide und ihre verwendung als herbizide |
| EP2589598A1 (de) * | 2011-11-03 | 2013-05-08 | Bayer CropScience AG | 5-Phenylsubstituierte N-(Tetrazol-5-yl)- und N-(Triazol-5-yl)arylcarbonsäureamide und ihre Verwendung als Herbizide |
| EP2589293A1 (de) * | 2011-11-03 | 2013-05-08 | Bayer CropScience AG | Herbizid-Safener-Zusammensetzungen enthaltend N-(Tetrazol-5-yl)- und N-(Triazol-5-yl)arylcarbonsäureamide |
| CN104428297A (zh) * | 2012-04-27 | 2015-03-18 | 巴斯夫欧洲公司 | 取代的n-(四唑-5-基)-和n-(三唑-5-基)芳基羧酰胺化合物及其作为除草剂的用途 |
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2013
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- 2013-04-30 KR KR20147030768A patent/KR20150003784A/ko not_active Ceased
- 2013-04-30 EP EP16179944.0A patent/EP3121172B1/de not_active Not-in-force
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- 2013-04-30 US US14/397,677 patent/US9371315B2/en not_active Expired - Fee Related
- 2013-04-30 BR BR112014027185A patent/BR112014027185B1/pt not_active IP Right Cessation
- 2013-04-30 CA CA 2872374 patent/CA2872374A1/en not_active Abandoned
- 2013-04-30 UA UAA201412738A patent/UA113545C2/uk unknown
- 2013-04-30 AU AU2013255929A patent/AU2013255929B2/en not_active Ceased
- 2013-04-30 EP EP13719550.9A patent/EP2844649A1/de not_active Withdrawn
- 2013-04-30 MX MX2014013159A patent/MX363987B/es active IP Right Grant
- 2013-04-30 ES ES16179944T patent/ES2705618T3/es active Active
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- 2013-04-30 HU HUE16179944A patent/HUE042768T2/hu unknown
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2014
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170129205A (ko) * | 2015-03-17 | 2017-11-24 | 바이엘 크롭사이언스 악티엔게젤샤프트 | N-(1,3,4-옥사디아졸-2-일)아릴 카복실산 아미드의 염 및 제초제로서의 그의 용도 |
Also Published As
| Publication number | Publication date |
|---|---|
| EA025517B1 (ru) | 2016-12-30 |
| AU2013255929A1 (en) | 2014-11-20 |
| BR112014027185B1 (pt) | 2019-10-22 |
| EP3121172B1 (de) | 2018-10-17 |
| HUE042768T2 (hu) | 2019-07-29 |
| MX363987B (es) | 2019-04-10 |
| IN2014DN08150A (OSRAM) | 2015-05-01 |
| ES2705618T3 (es) | 2019-03-26 |
| AR090939A1 (es) | 2014-12-17 |
| AU2013255929B2 (en) | 2017-02-16 |
| BR112014027185A2 (pt) | 2017-06-27 |
| CN104271563B (zh) | 2017-10-17 |
| PL3121172T3 (pl) | 2019-04-30 |
| EP2844649A1 (de) | 2015-03-11 |
| WO2013164331A1 (de) | 2013-11-07 |
| UA113545C2 (xx) | 2017-02-10 |
| EP3121172A1 (de) | 2017-01-25 |
| JP2015517456A (ja) | 2015-06-22 |
| MX2014013159A (es) | 2015-01-19 |
| ZA201408836B (en) | 2017-09-27 |
| CO7180218A2 (es) | 2015-02-09 |
| US9371315B2 (en) | 2016-06-21 |
| CA2872374A1 (en) | 2013-11-07 |
| US20150105253A1 (en) | 2015-04-16 |
| CN104271563A (zh) | 2015-01-07 |
| EA201401205A1 (ru) | 2015-04-30 |
| JP6104368B2 (ja) | 2017-03-29 |
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