CA1088060A - Substituted bicyclic triazoles - Google Patents
Substituted bicyclic triazolesInfo
- Publication number
- CA1088060A CA1088060A CA294,773A CA294773A CA1088060A CA 1088060 A CA1088060 A CA 1088060A CA 294773 A CA294773 A CA 294773A CA 1088060 A CA1088060 A CA 1088060A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- undesirable
- locus
- applying
- effective amount
- 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.)
- Expired
Links
- -1 bicyclic triazoles Chemical class 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 238000000034 method Methods 0.000 claims abstract description 54
- 235000017168 chlorine Nutrition 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 239000000460 chlorine Chemical group 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 34
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 235000019000 fluorine Nutrition 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 28
- 229910052794 bromium Inorganic materials 0.000 claims description 28
- 239000011737 fluorine Chemical group 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 150000002431 hydrogen Chemical group 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001309 chloro group Chemical class Cl* 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 125000001246 bromo group Chemical class Br* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- JKGVZTZZZQDRBT-UHFFFAOYSA-N 2-(2,4-dichloro-5-hydroxyphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(Cl)C(O)=CC(N2C(N3CCCCC3=N2)=O)=C1Cl JKGVZTZZZQDRBT-UHFFFAOYSA-N 0.000 claims description 2
- GRHZLQBPAJAHDM-SPRQWYLLSA-N [(3as,4r,6ar)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] n-[(2s,4s,5s)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate Chemical group CC1=CC=CC(C)=C1OCC(=O)N[C@H]([C@@H](O)C[C@H](CC=1C=CC=CC=1)NC(=O)O[C@@H]1[C@@H]2CCO[C@@H]2OC1)CC1=CC=CC=C1 GRHZLQBPAJAHDM-SPRQWYLLSA-N 0.000 claims 2
- PESHSRQWSRTLQT-UHFFFAOYSA-N 2-(2,4-dichloro-5-ethoxyphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(Cl)C(OCC)=CC(N2C(N3CCCCC3=N2)=O)=C1Cl PESHSRQWSRTLQT-UHFFFAOYSA-N 0.000 claims 1
- MJYODARZVYIKGH-UHFFFAOYSA-N 2-(2,4-dichloro-5-methoxyphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(Cl)C(OC)=CC(N2C(N3CCCCC3=N2)=O)=C1Cl MJYODARZVYIKGH-UHFFFAOYSA-N 0.000 claims 1
- XZLVBCLLBMAXLD-UHFFFAOYSA-N 2-(2,4-dichloro-5-propan-2-yloxyphenyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepin-3-one Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(N3CCCCCC3=N2)=O)=C1Cl XZLVBCLLBMAXLD-UHFFFAOYSA-N 0.000 claims 1
- 208000031968 Cadaver Diseases 0.000 claims 1
- XOEMATDHVZOBSG-UHFFFAOYSA-N azafenidin Chemical compound C1=C(OCC#C)C(Cl)=CC(Cl)=C1N1C(=O)N2CCCCC2=N1 XOEMATDHVZOBSG-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 32
- 239000004009 herbicide Substances 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 240000008042 Zea mays Species 0.000 description 29
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 29
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 29
- 235000005822 corn Nutrition 0.000 description 29
- 239000008187 granular material Substances 0.000 description 26
- 244000152970 Digitaria sanguinalis Species 0.000 description 24
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 244000075850 Avena orientalis Species 0.000 description 23
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 23
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 23
- 235000005476 Digitaria cruciata Nutrition 0.000 description 23
- 235000006830 Digitaria didactyla Nutrition 0.000 description 23
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 23
- 235000014716 Eleusine indica Nutrition 0.000 description 23
- 235000010469 Glycine max Nutrition 0.000 description 23
- 244000068988 Glycine max Species 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 241001506766 Xanthium Species 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
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- 240000006394 Sorghum bicolor Species 0.000 description 18
- 235000009566 rice Nutrition 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 244000037364 Cinnamomum aromaticum Species 0.000 description 17
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 17
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 17
- 229920000742 Cotton Polymers 0.000 description 16
- 235000007319 Avena orientalis Nutrition 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 241000209140 Triticum Species 0.000 description 15
- 235000021307 Triticum Nutrition 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 244000025254 Cannabis sativa Species 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- 239000008188 pellet Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 235000005853 Cyperus esculentus Nutrition 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 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 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 240000006995 Abutilon theophrasti Species 0.000 description 8
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 8
- 240000008853 Datura stramonium Species 0.000 description 8
- 235000021536 Sugar beet Nutrition 0.000 description 8
- 150000001411 amidrazones Chemical class 0.000 description 8
- 235000007320 Avena fatua Nutrition 0.000 description 7
- 241000192043 Echinochloa Species 0.000 description 7
- 241001355178 Setaria faberi Species 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 235000003403 Limnocharis flava Nutrition 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 235000017016 Setaria faberi Nutrition 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 240000001549 Ipomoea eriocarpa Species 0.000 description 5
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 235000009518 sodium iodide Nutrition 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
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- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
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Classifications
-
- 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
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- A01N47/02—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 no bond to a nitrogen atom
- A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; 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
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters 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
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- 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
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75899677A | 1977-01-13 | 1977-01-13 | |
| US758,996 | 1977-01-13 | ||
| US851,731 | 1977-11-17 | ||
| US05/851,731 US4213773A (en) | 1977-11-17 | 1977-11-17 | Herbicidal substituted bicyclic triazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1088060A true CA1088060A (en) | 1980-10-21 |
Family
ID=27116610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA294,773A Expired CA1088060A (en) | 1977-01-13 | 1978-01-11 | Substituted bicyclic triazoles |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS53105494A (cs) |
| AU (1) | AU3233478A (cs) |
| BR (1) | BR7800182A (cs) |
| CA (1) | CA1088060A (cs) |
| CS (1) | CS207497B2 (cs) |
| DE (1) | DE2801429A1 (cs) |
| DK (1) | DK538477A (cs) |
| ES (1) | ES465929A1 (cs) |
| FR (1) | FR2384769A1 (cs) |
| GB (1) | GB1561376A (cs) |
| GR (1) | GR65320B (cs) |
| IE (1) | IE46243B1 (cs) |
| IT (1) | IT1092731B (cs) |
| LU (1) | LU78858A1 (cs) |
| NL (1) | NL7800380A (cs) |
| PL (1) | PL109706B1 (cs) |
| TR (1) | TR20263A (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9265252B2 (en) | 2011-08-10 | 2016-02-23 | Bayer Intellectual Property Gmbh | Active compound combinations comprising specific tetramic acid derivatives |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59148785A (ja) * | 1983-02-15 | 1984-08-25 | Sumitomo Chem Co Ltd | ピリドトリアゾリウム誘導体、その製造法およびそれを有効成分とする除草剤 |
| DE3740837A1 (de) * | 1987-11-27 | 1989-06-08 | Schering Ag | Substituierte bicyclische triazole, verfahren zu ihrer herstellung und ihre verwendung als herbizide mittel |
| CA2090976C (en) * | 1990-09-13 | 2002-03-05 | Kofi Sam Amuti | Herbicidal substituted bicyclic triazoles |
| EP0784053A1 (de) * | 1996-01-15 | 1997-07-16 | Degussa Aktiengesellschaft | Verfahren zur Herstellung von Triazolinonherbiziden |
| JP2002320587A (ja) * | 2001-04-26 | 2002-11-05 | Asahi Optical Co Ltd | 内視鏡 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| DE1957783U (de) | 1966-11-16 | 1967-03-30 | Siemens Ag | Wicklung fuer elektrische maschinen mit fluessigkeitskuehlung. |
| DE2235177A1 (de) | 1972-07-18 | 1974-02-07 | Bayer Ag | Verfahren zur herstellung von lactamhydrazonen aromatischer systeme |
| DE2235113A1 (de) | 1972-07-18 | 1974-01-31 | Bayer Ag | Fungizides mittel |
| US3890342A (en) * | 1974-03-28 | 1975-06-17 | Velsicol Chemical Corp | 2-Alkyl-4-aryl-1,2,4-triazolidin-3-ones |
| US3958976A (en) * | 1975-02-03 | 1976-05-25 | E. I. Du Pont De Nemours And Company | 2-Aryl-5,6,7,8-tetrahydroimidazo[1,5a]-pyridine-1,3(2H,8aH)-diones as herbicides |
| CA1076114A (en) * | 1975-02-10 | 1980-04-22 | Mitsubishi Chemical Industries Limited | 1,5-alkylene-3-aryl hydantoin derivatives |
-
1977
- 1977-12-02 DK DK538477A patent/DK538477A/da not_active Application Discontinuation
-
1978
- 1978-01-11 CA CA294,773A patent/CA1088060A/en not_active Expired
- 1978-01-11 JP JP123378A patent/JPS53105494A/ja active Pending
- 1978-01-11 BR BR7800182A patent/BR7800182A/pt unknown
- 1978-01-11 IE IE59/78A patent/IE46243B1/en unknown
- 1978-01-11 AU AU32334/78A patent/AU3233478A/en active Pending
- 1978-01-12 NL NL7800380A patent/NL7800380A/xx not_active Application Discontinuation
- 1978-01-12 IT IT19188/78A patent/IT1092731B/it active
- 1978-01-12 FR FR7800795A patent/FR2384769A1/fr not_active Withdrawn
- 1978-01-12 CS CS78242A patent/CS207497B2/cs unknown
- 1978-01-12 GR GR55143A patent/GR65320B/el unknown
- 1978-01-12 ES ES465929A patent/ES465929A1/es not_active Expired
- 1978-01-12 GB GB1276/78A patent/GB1561376A/en not_active Expired
- 1978-01-12 LU LU78858A patent/LU78858A1/xx unknown
- 1978-01-13 TR TR20263A patent/TR20263A/xx unknown
- 1978-01-13 DE DE19782801429 patent/DE2801429A1/de not_active Withdrawn
- 1978-01-13 PL PL1978203976A patent/PL109706B1/pl unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9265252B2 (en) | 2011-08-10 | 2016-02-23 | Bayer Intellectual Property Gmbh | Active compound combinations comprising specific tetramic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| LU78858A1 (fr) | 1979-04-09 |
| FR2384769A1 (fr) | 1978-10-20 |
| JPS53105494A (en) | 1978-09-13 |
| TR20263A (tr) | 1980-12-08 |
| BR7800182A (pt) | 1978-08-22 |
| PL109706B1 (en) | 1980-06-30 |
| IT7819188A0 (it) | 1978-01-12 |
| IT1092731B (it) | 1985-07-12 |
| IE780059L (en) | 1978-07-13 |
| ES465929A1 (es) | 1978-12-01 |
| GB1561376A (en) | 1980-02-20 |
| PL203976A1 (pl) | 1978-10-23 |
| GR65320B (en) | 1980-08-11 |
| DE2801429A1 (de) | 1978-07-20 |
| DK538477A (da) | 1978-07-14 |
| AU3233478A (en) | 1979-07-19 |
| NL7800380A (nl) | 1978-07-17 |
| CS207497B2 (en) | 1981-07-31 |
| IE46243B1 (en) | 1983-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |