CS205149B2 - Herbicide,insecticide,fungicide or nematocide means and method of making the active substance - Google Patents
Herbicide,insecticide,fungicide or nematocide means and method of making the active substance Download PDFInfo
- Publication number
- CS205149B2 CS205149B2 CS795021A CS502179A CS205149B2 CS 205149 B2 CS205149 B2 CS 205149B2 CS 795021 A CS795021 A CS 795021A CS 502179 A CS502179 A CS 502179A CS 205149 B2 CS205149 B2 CS 205149B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- align
- carboxylic acid
- triazole
- isomeric mixture
- methyl
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 10
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 6
- 230000001069 nematicidal effect Effects 0.000 title claims abstract description 6
- 239000013543 active substance Substances 0.000 title description 29
- 239000004009 herbicide Substances 0.000 title description 4
- 239000000417 fungicide Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000002917 insecticide Substances 0.000 title description 2
- 239000005645 nematicide Substances 0.000 title description 2
- OSKSVLBJJXQUPI-UHFFFAOYSA-N 2h-triazole-4-carboxamide Chemical class NC(=O)C1=CNN=N1 OSKSVLBJJXQUPI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 150
- -1 -allyl Chemical group 0.000 claims description 32
- 239000004480 active ingredient Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 150000000177 1,2,3-triazoles Chemical class 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 92
- 230000000895 acaricidal effect Effects 0.000 abstract description 3
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 33
- 230000000694 effects Effects 0.000 description 32
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 23
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 22
- 238000011282 treatment Methods 0.000 description 18
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 17
- 239000007921 spray Substances 0.000 description 17
- 230000006378 damage Effects 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
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- 235000021186 dishes Nutrition 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 6
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 6
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 6
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 125000006127 1-methylpropyl sulfonyl group Chemical group 0.000 description 4
- 125000004709 1-methylpropylthio group Chemical group CC(CC)S* 0.000 description 4
- VEDXNNRTYCLCMP-UHFFFAOYSA-N 4-methylsulfanyl-2h-triazole Chemical compound CSC1=CNN=N1 VEDXNNRTYCLCMP-UHFFFAOYSA-N 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- 150000007513 acids Chemical class 0.000 description 4
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- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 4
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- 235000009973 maize Nutrition 0.000 description 4
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 4
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- 230000021235 carbamoylation Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- WCYBYZBPWZTMDW-UHFFFAOYSA-N dibutylazanide Chemical compound CCCC[N-]CCCC WCYBYZBPWZTMDW-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
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- OJKZEZMAPKWHTG-UHFFFAOYSA-N bis(2h-triazol-4-yl)methanone Chemical class C=1NN=NC=1C(=O)C1=CNN=N1 OJKZEZMAPKWHTG-UHFFFAOYSA-N 0.000 description 1
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- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
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- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- OWRABTHGOKNUDV-UHFFFAOYSA-N n,n-dipropylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)CCC OWRABTHGOKNUDV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KCNUWLJAWRWKMO-UHFFFAOYSA-N n-ethyl-n-propyl-3-propylsulfonyl-1,2,4-triazole-1-carboxamide Chemical compound CCCN(CC)C(=O)N1C=NC(S(=O)(=O)CCC)=N1 KCNUWLJAWRWKMO-UHFFFAOYSA-N 0.000 description 1
- SRTHFWNTKVOSBA-UHFFFAOYSA-N n-ethylcyclopentanamine Chemical compound CCNC1CCCC1 SRTHFWNTKVOSBA-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
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- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
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- 235000012015 potatoes Nutrition 0.000 description 1
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- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- 229940055764 triaz Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
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- 150000003672 ureas Chemical class 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D249/04—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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| CS205149B2 true CS205149B2 (en) | 1981-04-30 |
Family
ID=6046591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS795021A CS205149B2 (en) | 1978-08-07 | 1979-07-18 | Herbicide,insecticide,fungicide or nematocide means and method of making the active substance |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US4233059A (ro) |
| JP (1) | JPS5524179A (ro) |
| AR (1) | AR222039A1 (ro) |
| AT (1) | AT365892B (ro) |
| AU (1) | AU523909B2 (ro) |
| BE (1) | BE878127A (ro) |
| BR (1) | BR7905011A (ro) |
| CA (1) | CA1129425A (ro) |
| CH (1) | CH640518A5 (ro) |
| CS (1) | CS205149B2 (ro) |
| DD (1) | DD145364A5 (ro) |
| DE (1) | DE2834879A1 (ro) |
| DK (1) | DK301879A (ro) |
| EG (1) | EG14370A (ro) |
| ES (1) | ES483115A1 (ro) |
| FI (1) | FI792423A7 (ro) |
| FR (1) | FR2433018A1 (ro) |
| GB (1) | GB2028319B (ro) |
| GR (1) | GR72718B (ro) |
| IE (1) | IE48787B1 (ro) |
| IL (1) | IL57927A (ro) |
| IN (1) | IN152609B (ro) |
| IT (1) | IT1122324B (ro) |
| LU (1) | LU81578A1 (ro) |
| MA (1) | MA18557A1 (ro) |
| MX (1) | MX5623E (ro) |
| NL (1) | NL7904611A (ro) |
| NO (1) | NO792575L (ro) |
| NZ (1) | NZ191185A (ro) |
| PH (1) | PH16769A (ro) |
| PL (1) | PL118237B1 (ro) |
| PT (1) | PT69999A (ro) |
| RO (2) | RO81505B (ro) |
| SE (1) | SE7906602L (ro) |
| SU (1) | SU929008A3 (ro) |
| TR (1) | TR20593A (ro) |
| YU (1) | YU149179A (ro) |
| ZA (1) | ZA794084B (ro) |
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 |
| US4596596A (en) * | 1985-06-21 | 1986-06-24 | Stauffer Chemical Company | 1-,2-,and 3-N,N-dialkylcarbamyl-1-H-1,2,3-triazoles |
| 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 |
| 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 |
| EP2258690B1 (en) * | 2002-08-22 | 2013-02-20 | Syngenta Participations AG | Tricyclic amines as intermediates in the synthesis of fungicidal carboxamide derivatives |
| 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 |
| US9108930B2 (en) * | 2011-04-06 | 2015-08-18 | The Scripps Research Institute | N1- and N2-carbamoyl-1,2,3-triazole serine hydrolase inhibitors and methods |
| 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 AR AR277299A patent/AR222039A1/es active
- 1979-07-13 IN IN507/DEL/79A patent/IN152609B/en unknown
- 1979-07-18 DK DK301879A patent/DK301879A/da not_active Application Discontinuation
- 1979-07-18 CS CS795021A patent/CS205149B2/cs unknown
- 1979-07-25 IT IT24631/79A patent/IT1122324B/it active
- 1979-07-30 CA CA332,838A patent/CA1129425A/en not_active Expired
- 1979-07-30 GB GB7926412A patent/GB2028319B/en not_active Expired
- 1979-07-30 PT PT69999A patent/PT69999A/pt unknown
- 1979-07-31 IL IL57927A patent/IL57927A/xx unknown
- 1979-08-01 NZ NZ191185A patent/NZ191185A/xx unknown
- 1979-08-01 US US06/062,795 patent/US4233059A/en not_active Expired - Lifetime
- 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 FI FI792423A patent/FI792423A7/fi not_active Application Discontinuation
- 1979-08-03 MA MA18755A patent/MA18557A1/fr unknown
- 1979-08-06 FR FR7920083A patent/FR2433018A1/fr active Granted
- 1979-08-06 TR TR20593A patent/TR20593A/xx unknown
- 1979-08-06 CH CH721279A patent/CH640518A5/de not_active IP Right Cessation
- 1979-08-06 AU AU49594/79A patent/AU523909B2/en not_active Ceased
- 1979-08-06 GR GR59781A patent/GR72718B/el unknown
- 1979-08-06 PL PL1979217595A patent/PL118237B1/pl unknown
- 1979-08-06 RO RO103432A patent/RO81505B/ro unknown
- 1979-08-06 BR BR7905011A patent/BR7905011A/pt unknown
- 1979-08-06 RO RO7998383A patent/RO77561A/ro unknown
- 1979-08-06 NO NO792575A patent/NO792575L/no unknown
- 1979-08-06 AT AT0536579A patent/AT365892B/de not_active IP Right Cessation
- 1979-08-06 EG EG476/79A patent/EG14370A/xx active
- 1979-08-06 PH PH22864A patent/PH16769A/en unknown
- 1979-08-06 SU SU792797788A patent/SU929008A3/ru active
- 1979-08-06 SE SE7906602A patent/SE7906602L/xx unknown
- 1979-08-06 LU LU81578A patent/LU81578A1/de unknown
- 1979-08-07 JP JP9993379A patent/JPS5524179A/ja active Pending
- 1979-08-07 ZA ZA00794084A patent/ZA794084B/xx unknown
- 1979-08-07 BE BE0/196637A patent/BE878127A/fr not_active IP Right Cessation
- 1979-08-08 IE IE1488/79A patent/IE48787B1/en unknown
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