IE46243B1 - 2-phenyl-bicyclic-1,2,4-triazoles and their use as herbicides - Google Patents
2-phenyl-bicyclic-1,2,4-triazoles and their use as herbicidesInfo
- Publication number
- IE46243B1 IE46243B1 IE59/78A IE5978A IE46243B1 IE 46243 B1 IE46243 B1 IE 46243B1 IE 59/78 A IE59/78 A IE 59/78A IE 5978 A IE5978 A IE 5978A IE 46243 B1 IE46243 B1 IE 46243B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- chlorine
- hydrogen
- bromine
- fluorine
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 35
- -1 bicyclic triazole compounds Chemical class 0.000 claims abstract description 20
- 239000000460 chlorine Chemical group 0.000 claims description 54
- 229910052801 chlorine Inorganic materials 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 45
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 37
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 37
- 229910052794 bromium Inorganic materials 0.000 claims description 37
- 239000011737 fluorine Chemical group 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
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- 235000021307 Triticum Nutrition 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 7
- 235000021536 Sugar beet Nutrition 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- TUKGDZUWOOQEPY-UHFFFAOYSA-N 2-(2,4-dichloro-5-propan-2-yloxyphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(N3CCCCC3=N2)=O)=C1Cl TUKGDZUWOOQEPY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 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 3
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- 125000000304 alkynyl group Chemical group 0.000 claims description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
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- 229940125758 compound 15 Drugs 0.000 claims 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
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- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000001238 wet grinding Methods 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75899677A | 1977-01-13 | 1977-01-13 | |
| US05/851,731 US4213773A (en) | 1977-11-17 | 1977-11-17 | Herbicidal substituted bicyclic triazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE780059L IE780059L (en) | 1978-07-13 |
| IE46243B1 true IE46243B1 (en) | 1983-04-06 |
Family
ID=27116610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE59/78A IE46243B1 (en) | 1977-01-13 | 1978-01-11 | 2-phenyl-bicyclic-1,2,4-triazoles and their use as herbicides |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS53105494A (fr) |
| AU (1) | AU3233478A (fr) |
| BR (1) | BR7800182A (fr) |
| CA (1) | CA1088060A (fr) |
| CS (1) | CS207497B2 (fr) |
| DE (1) | DE2801429A1 (fr) |
| DK (1) | DK538477A (fr) |
| ES (1) | ES465929A1 (fr) |
| FR (1) | FR2384769A1 (fr) |
| GB (1) | GB1561376A (fr) |
| GR (1) | GR65320B (fr) |
| IE (1) | IE46243B1 (fr) |
| IT (1) | IT1092731B (fr) |
| LU (1) | LU78858A1 (fr) |
| NL (1) | NL7800380A (fr) |
| PL (1) | PL109706B1 (fr) |
| TR (1) | TR20263A (fr) |
Families Citing this family (6)
| 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 |
| MY111872A (en) * | 1990-09-13 | 2001-02-28 | Du Pont | Herbicidal substituted bicyclic triazoles |
| EP0784053A1 (fr) * | 1996-01-15 | 1997-07-16 | Degussa Aktiengesellschaft | Procédé pour la préparation des triazolinones comme herbicides |
| JP2002320587A (ja) * | 2001-04-26 | 2002-11-05 | Asahi Optical Co Ltd | 内視鏡 |
| BR112014002855A2 (pt) | 2011-08-10 | 2017-02-21 | Bayer Ip Gmbh | combinações do composto ativo que incluem derivados específicos do ácido tetrâmico |
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. |
| DE2235113A1 (de) | 1972-07-18 | 1974-01-31 | Bayer Ag | Fungizides mittel |
| DE2235177A1 (de) | 1972-07-18 | 1974-02-07 | Bayer Ag | Verfahren zur herstellung von lactamhydrazonen aromatischer systeme |
| 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 (fr) * | 1975-02-10 | 1980-04-22 | Mitsubishi Chemical Industries Limited | Derives de 1,5-alkylene-3-arylhydantone |
-
1977
- 1977-12-02 DK DK538477A patent/DK538477A/da not_active Application Discontinuation
-
1978
- 1978-01-11 CA CA294,773A patent/CA1088060A/fr not_active Expired
- 1978-01-11 JP JP123378A patent/JPS53105494A/ja active Pending
- 1978-01-11 AU AU32334/78A patent/AU3233478A/en active Pending
- 1978-01-11 IE IE59/78A patent/IE46243B1/en unknown
- 1978-01-11 BR BR7800182A patent/BR7800182A/pt unknown
- 1978-01-12 ES ES465929A patent/ES465929A1/es not_active Expired
- 1978-01-12 FR FR7800795A patent/FR2384769A1/fr not_active Withdrawn
- 1978-01-12 LU LU78858A patent/LU78858A1/fr unknown
- 1978-01-12 IT IT19188/78A patent/IT1092731B/it active
- 1978-01-12 GB GB1276/78A patent/GB1561376A/en not_active Expired
- 1978-01-12 CS CS78242A patent/CS207497B2/cs unknown
- 1978-01-12 GR GR55143A patent/GR65320B/el unknown
- 1978-01-12 NL NL7800380A patent/NL7800380A/xx not_active Application Discontinuation
- 1978-01-13 PL PL1978203976A patent/PL109706B1/pl unknown
- 1978-01-13 DE DE19782801429 patent/DE2801429A1/de not_active Withdrawn
- 1978-01-13 TR TR20263A patent/TR20263A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2384769A1 (fr) | 1978-10-20 |
| DK538477A (da) | 1978-07-14 |
| ES465929A1 (es) | 1978-12-01 |
| LU78858A1 (fr) | 1979-04-09 |
| GR65320B (en) | 1980-08-11 |
| BR7800182A (pt) | 1978-08-22 |
| IT7819188A0 (it) | 1978-01-12 |
| CS207497B2 (en) | 1981-07-31 |
| TR20263A (tr) | 1980-12-08 |
| IT1092731B (it) | 1985-07-12 |
| CA1088060A (fr) | 1980-10-21 |
| AU3233478A (en) | 1979-07-19 |
| GB1561376A (en) | 1980-02-20 |
| NL7800380A (nl) | 1978-07-17 |
| IE780059L (en) | 1978-07-13 |
| PL203976A1 (pl) | 1978-10-23 |
| PL109706B1 (en) | 1980-06-30 |
| JPS53105494A (en) | 1978-09-13 |
| DE2801429A1 (de) | 1978-07-20 |
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