NL7904611A - Triazoolcarbonzuuramiden, werkwijze voor het bereiden daarvan, alsmede biociden op basis van deze verbin- dingen. - Google Patents
Triazoolcarbonzuuramiden, werkwijze voor het bereiden daarvan, alsmede biociden op basis van deze verbin- dingen. Download PDFInfo
- Publication number
- NL7904611A NL7904611A NL7904611A NL7904611A NL7904611A NL 7904611 A NL7904611 A NL 7904611A NL 7904611 A NL7904611 A NL 7904611A NL 7904611 A NL7904611 A NL 7904611A NL 7904611 A NL7904611 A NL 7904611A
- Authority
- NL
- Netherlands
- Prior art keywords
- triazole
- carboxylic acid
- amide
- methyl
- ethyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 141
- 238000000034 method Methods 0.000 title claims description 22
- 239000003139 biocide Substances 0.000 title claims description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title claims 2
- 150000003852 triazoles Chemical class 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 151
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 50
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 42
- -1 morpholino, piperidino, pyrrolidino Chemical group 0.000 claims description 41
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims description 27
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 150000001408 amides Chemical class 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 150000003931 anilides Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 12
- 230000000855 fungicidal effect Effects 0.000 claims description 11
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 claims description 10
- WCYBYZBPWZTMDW-UHFFFAOYSA-N dibutylazanide Chemical compound CCCC[N-]CCCC WCYBYZBPWZTMDW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000006127 1-methylpropyl sulfonyl group Chemical group 0.000 claims description 9
- OSKSVLBJJXQUPI-UHFFFAOYSA-N 2h-triazole-4-carboxamide Chemical class NC(=O)C1=CNN=N1 OSKSVLBJJXQUPI-UHFFFAOYSA-N 0.000 claims description 9
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000004709 1-methylpropylthio group Chemical group CC(CC)S* 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- 239000004009 herbicide Substances 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 239000000417 fungicide Substances 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- OJKZEZMAPKWHTG-UHFFFAOYSA-N bis(2h-triazol-4-yl)methanone Chemical class C=1NN=NC=1C(=O)C1=CNN=N1 OJKZEZMAPKWHTG-UHFFFAOYSA-N 0.000 claims description 4
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005394 methallyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000000177 1,2,3-triazoles Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002641 lithium Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- RTFCDZNVVOREPY-UHFFFAOYSA-N FC(CCCN)CC Chemical compound FC(CCCN)CC RTFCDZNVVOREPY-UHFFFAOYSA-N 0.000 claims 1
- 241000010957 Leuciscus waleckii Species 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 60
- 230000008018 melting Effects 0.000 description 60
- 241000196324 Embryophyta Species 0.000 description 38
- 230000000694 effects Effects 0.000 description 26
- 239000007788 liquid Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VEDXNNRTYCLCMP-UHFFFAOYSA-N 4-methylsulfanyl-2h-triazole Chemical compound CSC1=CNN=N1 VEDXNNRTYCLCMP-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- 235000021186 dishes Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 206010061217 Infestation Diseases 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- 241000219146 Gossypium Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- 239000002689 soil Substances 0.000 description 5
- URSNTRUKGDZNFR-UHFFFAOYSA-N 5-butylsulfonyl-4,5-dihydro-1H-triazole Chemical compound C(CCC)S(=O)(=O)C1NN=NC1 URSNTRUKGDZNFR-UHFFFAOYSA-N 0.000 description 4
- 241000238657 Blattella germanica 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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- 240000002024 Gossypium herbaceum Species 0.000 description 4
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000021235 carbamoylation Effects 0.000 description 4
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- AACACTZERFCGJT-UHFFFAOYSA-N 4-benzylsulfanyl-2h-triazole Chemical compound C=1C=CC=CC=1CSC1=CNN=N1 AACACTZERFCGJT-UHFFFAOYSA-N 0.000 description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 3
- XZLUHSSJBLSHNS-UHFFFAOYSA-N 4-propylsulfanyl-2h-triazole Chemical compound CCCSC=1C=NNN=1 XZLUHSSJBLSHNS-UHFFFAOYSA-N 0.000 description 3
- MGONQRDUSRTESM-UHFFFAOYSA-N 5-ethylsulfonyl-4,5-dihydro-1H-triazole Chemical compound C(C)S(=O)(=O)C1NN=NC1 MGONQRDUSRTESM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 244000075850 Avena orientalis Species 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RRCYYLHJWRYWEI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOO RRCYYLHJWRYWEI-UHFFFAOYSA-N 0.000 description 3
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- 230000008901 benefit Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
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- DORKSRRTHNCISG-UHFFFAOYSA-N 4-ethylsulfanyl-2h-triazole Chemical compound CCSC=1C=NNN=1 DORKSRRTHNCISG-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2834879 | 1978-08-07 | ||
| DE19782834879 DE2834879A1 (de) | 1978-08-07 | 1978-08-07 | 1,2,3-triazolcarbonsaeureamide, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7904611A true NL7904611A (nl) | 1980-02-11 |
Family
ID=6046591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7904611A NL7904611A (nl) | 1978-08-07 | 1979-06-12 | Triazoolcarbonzuuramiden, werkwijze voor het bereiden daarvan, alsmede biociden op basis van deze verbin- dingen. |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US4233059A (cs) |
| JP (1) | JPS5524179A (cs) |
| AR (1) | AR222039A1 (cs) |
| AT (1) | AT365892B (cs) |
| AU (1) | AU523909B2 (cs) |
| BE (1) | BE878127A (cs) |
| BR (1) | BR7905011A (cs) |
| CA (1) | CA1129425A (cs) |
| CH (1) | CH640518A5 (cs) |
| CS (1) | CS205149B2 (cs) |
| DD (1) | DD145364A5 (cs) |
| DE (1) | DE2834879A1 (cs) |
| DK (1) | DK301879A (cs) |
| EG (1) | EG14370A (cs) |
| ES (1) | ES483115A1 (cs) |
| FI (1) | FI792423A7 (cs) |
| FR (1) | FR2433018A1 (cs) |
| GB (1) | GB2028319B (cs) |
| GR (1) | GR72718B (cs) |
| IE (1) | IE48787B1 (cs) |
| IL (1) | IL57927A (cs) |
| IN (1) | IN152609B (cs) |
| IT (1) | IT1122324B (cs) |
| LU (1) | LU81578A1 (cs) |
| MA (1) | MA18557A1 (cs) |
| MX (1) | MX5623E (cs) |
| NL (1) | NL7904611A (cs) |
| NO (1) | NO792575L (cs) |
| NZ (1) | NZ191185A (cs) |
| PH (1) | PH16769A (cs) |
| PL (1) | PL118237B1 (cs) |
| PT (1) | PT69999A (cs) |
| RO (2) | RO77561A (cs) |
| SE (1) | SE7906602L (cs) |
| SU (1) | SU929008A3 (cs) |
| TR (1) | TR20593A (cs) |
| YU (1) | YU149179A (cs) |
| ZA (1) | ZA794084B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4280831A (en) * | 1980-08-04 | 1981-07-28 | Gulf Oil Corporation | Benzylsulfonyl diethylcarbamyl triazole and use as a selective herbicide |
| US4596597A (en) * | 1985-06-21 | 1986-06-24 | Stauffer Chemical Company | Esters of 1,2 and 3-N,N-dialkylcarbamyl-5-substituted-1H-1,2,3-triazole-4-carboxylic acid |
| US4596596A (en) * | 1985-06-21 | 1986-06-24 | Stauffer Chemical Company | 1-,2-,and 3-N,N-dialkylcarbamyl-1-H-1,2,3-triazoles |
| JPH0559017A (ja) * | 1990-10-26 | 1993-03-09 | Ube Ind Ltd | １，２，３−トリアゾール誘導体、その製法及び有害生物防除剤 |
| JP4643441B2 (ja) * | 2002-08-22 | 2011-03-02 | シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト | 化合物 |
| TWI469979B (zh) * | 2008-12-24 | 2015-01-21 | Bial Portela & Ca Sa | 脂肪酸醯胺水解酶(faah)抑制劑、以及其藥學組成物與用途 |
| EP2712291A4 (en) * | 2011-04-06 | 2014-11-05 | Scripps Research Inst | N1 AND N2 CARBAMOYL-1,2,3-TRIAZOL SERINE HYDROLASE INHIBITORS AND METHOD THEREFOR |
| CN102775361B (zh) * | 2012-07-27 | 2014-11-12 | 浙江工业大学 | 一种1,2,4-三唑类衍生物、其制备方法及用途 |
| US11085342B2 (en) | 2018-06-20 | 2021-08-10 | Ngk Insulators, Ltd. | Honeycomb filter |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3952001A (en) | 1970-07-01 | 1976-04-20 | The Boots Company Limited | 1-Carbamoyl-1,2,4-triazoles |
-
1978
- 1978-08-07 DE DE19782834879 patent/DE2834879A1/de not_active Withdrawn
-
1979
- 1979-06-12 NL NL7904611A patent/NL7904611A/nl not_active Application Discontinuation
- 1979-06-25 YU YU01491/79A patent/YU149179A/xx unknown
- 1979-07-13 IN IN507/DEL/79A patent/IN152609B/en unknown
- 1979-07-13 AR AR277299A patent/AR222039A1/es active
- 1979-07-18 CS CS795021A patent/CS205149B2/cs unknown
- 1979-07-18 DK DK301879A patent/DK301879A/da not_active Application Discontinuation
- 1979-07-25 IT IT24631/79A patent/IT1122324B/it active
- 1979-07-30 GB GB7926412A patent/GB2028319B/en not_active Expired
- 1979-07-30 PT PT69999A patent/PT69999A/pt unknown
- 1979-07-30 CA CA332,838A patent/CA1129425A/en not_active Expired
- 1979-07-31 IL IL57927A patent/IL57927A/xx unknown
- 1979-08-01 US US06/062,795 patent/US4233059A/en not_active Expired - Lifetime
- 1979-08-01 NZ NZ191185A patent/NZ191185A/xx unknown
- 1979-08-02 MX MX798297U patent/MX5623E/es unknown
- 1979-08-02 DD DD79214769A patent/DD145364A5/de unknown
- 1979-08-03 ES ES483115A patent/ES483115A1/es not_active Expired
- 1979-08-03 MA MA18755A patent/MA18557A1/fr unknown
- 1979-08-03 FI FI792423A patent/FI792423A7/fi not_active Application Discontinuation
- 1979-08-06 SE SE7906602A patent/SE7906602L/xx unknown
- 1979-08-06 RO RO7998383A patent/RO77561A/ro unknown
- 1979-08-06 BR BR7905011A patent/BR7905011A/pt unknown
- 1979-08-06 PH PH22864A patent/PH16769A/en unknown
- 1979-08-06 NO NO792575A patent/NO792575L/no unknown
- 1979-08-06 FR FR7920083A patent/FR2433018A1/fr active Granted
- 1979-08-06 RO RO103432A patent/RO81505B/ro unknown
- 1979-08-06 CH CH721279A patent/CH640518A5/de not_active IP Right Cessation
- 1979-08-06 GR GR59781A patent/GR72718B/el unknown
- 1979-08-06 TR TR20593A patent/TR20593A/xx unknown
- 1979-08-06 AU AU49594/79A patent/AU523909B2/en not_active Ceased
- 1979-08-06 AT AT0536579A patent/AT365892B/de not_active IP Right Cessation
- 1979-08-06 LU LU81578A patent/LU81578A1/de unknown
- 1979-08-06 SU SU792797788A patent/SU929008A3/ru active
- 1979-08-06 PL PL1979217595A patent/PL118237B1/pl unknown
- 1979-08-06 EG EG476/79A patent/EG14370A/xx active
- 1979-08-07 ZA ZA00794084A patent/ZA794084B/xx unknown
- 1979-08-07 BE BE0/196637A patent/BE878127A/fr not_active IP Right Cessation
- 1979-08-07 JP JP9993379A patent/JPS5524179A/ja active Pending
- 1979-08-08 IE IE1488/79A patent/IE48787B1/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |