IE37629B1 - S-triazinediones and their use as herbicides - Google Patents
S-triazinediones and their use as herbicidesInfo
- Publication number
- IE37629B1 IE37629B1 IE762/73A IE76273A IE37629B1 IE 37629 B1 IE37629 B1 IE 37629B1 IE 762/73 A IE762/73 A IE 762/73A IE 76273 A IE76273 A IE 76273A IE 37629 B1 IE37629 B1 IE 37629B1
- Authority
- IE
- Ireland
- Prior art keywords
- carbon atoms
- formula
- alkyl
- hydrogen
- chlorine
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title abstract 2
- GEWRKGDRYZIFNP-UHFFFAOYSA-N 1h-1,3,5-triazine-2,4-dione Chemical class OC1=NC=NC(O)=N1 GEWRKGDRYZIFNP-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 16
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- -1 trimethylcyclohexyl Chemical group 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical class O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- YSKUZVBSHIWEFK-UHFFFAOYSA-N ammelide Chemical class NC1=NC(O)=NC(O)=N1 YSKUZVBSHIWEFK-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 150000001602 bicycloalkyls Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 150000001805 chlorine compounds Chemical group 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- ZSYJMXLJNPEAGP-UHFFFAOYSA-N methyl n-cyanocarbamate Chemical compound COC(=O)NC#N ZSYJMXLJNPEAGP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1435585 6-Amino-s-triazin-2,4[1H,3H]-dione derivatives E I DU PONT DE NEMOURS & CO 23 May 1973 [24 May 1972 5 April 1973 (2)] 24677/73 Headings A5E E1C5J E1C5P E1C5M E1C14A E1C15D3 E1A3B ElA3Cand E1A5B3 Novel compounds have the Formula I wherein R 1 is selected from (a) alkyl of 2 to 8 carbon atoms, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, cycloalkyl of 4 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms, cycloalkylmethyl of 4 to 9 carbon atoms, cycloalkenylmethyl of 6 to 9 carbon atoms, bicycloalkyl or bicycloalkenyl of 7 to 10 carbon atoms and bicycloalkylmethyl or bicycloalkenylmethyl of 8 to 11 carbon atoms, trimethylcyclohexyl and tetramethylcyclohexyl; (b) the above alkyl groups substituted with one methoxy, ethoxy, methylthio or ethylthio group; (c) the above cycloalkyl groups substituted with one alkyl group of 2 to 4 carbon atoms, 1 or 2 methyl groups, 1 or 2 chlorine or bromine atoms, one methoxy or one ethoxy group; and (d) a group of Formula wherein Q is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of alkylthio of 1 or 2 carbon atoms, nitro or a trifluoromethyl group; Y is hydrogen, chlorine or methyl; and Z is hydrogen or chlorine; R 2 is hydrogen, alkyl of 1 to 3 carbon atoms or a cation selected from Na<SP>+</SP>, Li<SP>+</SP>, K<SP>+</SP>, (Ca/2)<SP>+</SP>, ammonium and dimethylammonium; R 2 is hydrogen, methyl or ethyl; R 4 is alkyl of 1 to 4 carbon atoms, alkenyl of 3 or 4 carbon atoms, alkynyl of 3 or 4 carbon atoms, or methoxy; and X is oxygen or sulphur; provided that when X is sulphur, neither R 2 nor R 3 is hydrogen. The compounds of Formula I are prepared, for example, by reaction of a corresponding 6- methylthio compound with an amine of Formula R 3 R 4 NH or, in the case of a 4-thio derivative, by reaction of P 2 S 5 with the corresponding 2,4-dione derivative. The compounds of Formula I in which R 2 is alkyl [=R<SP>1</SP> 2 ] are also obtained by cyclization, in the presence of a base (an alkali metal C 1-4 alkoxide), of a compound of Formula CH 3 O-CO-NR<SP>1</SP> 2 -C(NR 3 R 4 )=N-CX-NHR 1 These latter starting materials are themselves obtained by reacting methoxycarbonyl-cyanamide with an alkylating agent of Formula R<SP>1</SP> 2 -Q [Q = chloride, bromide, iodide or -O-SO 2 OR<SP>1</SP> 2 ] to form N-methoxycarbonyl-N-alkylcyanamide, reacting the latter with an amine of Formula R 3 R 4 NH to form a compound of Formula CH 3 O-CO-NR<SP>1</SP> 2 -C(NR 3 R 4 )=NH and then reacting this intermediate with an isocyanate or isothiocyanate of Formula R 1 NCX. The compounds of Formula I are herbicides.
[GB1435585A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25624972A | 1972-05-24 | 1972-05-24 | |
| US34832173A | 1973-04-05 | 1973-04-05 | |
| US00348324A US3850924A (en) | 1973-04-05 | 1973-04-05 | Process for preparing herbicidal triazines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37629L IE37629L (en) | 1973-11-24 |
| IE37629B1 true IE37629B1 (en) | 1977-08-31 |
Family
ID=27400932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE762/73A IE37629B1 (en) | 1972-05-24 | 1973-05-15 | S-triazinediones and their use as herbicides |
Country Status (30)
| Country | Link |
|---|---|
| JP (2) | JPS5418339B2 (en) |
| AR (1) | AR213607A1 (en) |
| BG (1) | BG22363A3 (en) |
| CH (1) | CH583506A5 (en) |
| CY (1) | CY972A (en) |
| DD (2) | DD106938A5 (en) |
| DE (1) | DE2326358C3 (en) |
| DK (1) | DK139911B (en) |
| EG (1) | EG10976A (en) |
| ES (1) | ES441014A1 (en) |
| FI (1) | FI57940C (en) |
| FR (1) | FR2185625B1 (en) |
| GB (1) | GB1435585A (en) |
| HK (1) | HK31378A (en) |
| HU (1) | HU167436B (en) |
| IE (1) | IE37629B1 (en) |
| IL (1) | IL42103A (en) |
| IN (1) | IN139019B (en) |
| IT (1) | IT987878B (en) |
| KE (1) | KE2845A (en) |
| LU (1) | LU67653A1 (en) |
| MX (1) | MX147114A (en) |
| MY (1) | MY7800316A (en) |
| NL (1) | NL160259C (en) |
| NO (2) | NO140268C (en) |
| OA (1) | OA04410A (en) |
| RO (2) | RO68557A (en) |
| SU (1) | SU616994A3 (en) |
| YU (6) | YU137073A (en) |
| ZM (1) | ZM8373A1 (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2254200C2 (en) * | 1972-11-06 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | Tetrahydro-1,3,5-triazine-2,6-diones, process for their preparation and their use as herbicides |
| JPS602306B2 (en) * | 1972-11-06 | 1985-01-21 | バイエル アクチエンゲゼルシヤフト | Method for producing tetrahydro-1,3,5-triazine-2,6-diones |
| US4226990A (en) * | 1973-11-01 | 1980-10-07 | Imperial Chemical Industries Limited | Triazine-diones |
| GB1543037A (en) * | 1975-02-05 | 1979-03-28 | Ici Ltd | Selective herbicidal triazine-diones |
| AU509813B2 (en) * | 1975-05-05 | 1980-05-29 | E.I. Du Pont De Nemours And Company | Preparation of triazine-diones |
| US4197112A (en) * | 1977-10-12 | 1980-04-08 | E. I. Du Pont De Nemours And Company | Water-dispersible herbicide compositions |
| US4246409A (en) * | 1978-11-13 | 1981-01-20 | William H. Rorer, Inc. | Triazinones |
| CZ146296A3 (en) * | 1995-06-02 | 1997-04-16 | American Cyanamid Co | 3-(3-aryloxyphenyl)-1-(substituted methyl)-s-triazine-2,4,6-oxo or thiotriones, process of their preparation and herbicidal agents |
| AU2022240693A1 (en) * | 2021-03-17 | 2023-09-07 | Hansoh Bio Llc | Nitrogen-containing heterocyclic ketones, preparation methods and medicinal uses thereof |
| EP4527837A1 (en) * | 2022-05-20 | 2025-03-26 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Crystal forms of triazine dione derivative and preparation method therefor |
-
1973
- 1973-04-25 IL IL42103A patent/IL42103A/en unknown
- 1973-04-26 IN IN980/CAL/73A patent/IN139019B/en unknown
- 1973-05-14 ZM ZM83/73A patent/ZM8373A1/en unknown
- 1973-05-15 IE IE762/73A patent/IE37629B1/en unknown
- 1973-05-16 AR AR248054A patent/AR213607A1/en active
- 1973-05-17 OA OA54914A patent/OA04410A/en unknown
- 1973-05-22 EG EG189/73A patent/EG10976A/en active
- 1973-05-22 DD DD170989A patent/DD106938A5/xx unknown
- 1973-05-22 DD DD179515*A patent/DD112651A5/xx unknown
- 1973-05-22 JP JP5642873A patent/JPS5418339B2/ja not_active Expired
- 1973-05-22 BG BG023690A patent/BG22363A3/en unknown
- 1973-05-23 HU HUDU203A patent/HU167436B/hu unknown
- 1973-05-23 CY CY972A patent/CY972A/en unknown
- 1973-05-23 DK DK283473AA patent/DK139911B/en not_active IP Right Cessation
- 1973-05-23 GB GB2467773A patent/GB1435585A/en not_active Expired
- 1973-05-23 RO RO7383863A patent/RO68557A/en unknown
- 1973-05-23 RO RO74881A patent/RO71605B/en unknown
- 1973-05-23 DE DE2326358A patent/DE2326358C3/en not_active Expired
- 1973-05-23 LU LU67653A patent/LU67653A1/xx unknown
- 1973-05-23 FI FI1667/73A patent/FI57940C/en active
- 1973-05-23 SU SU731923101A patent/SU616994A3/en active
- 1973-05-23 NL NL7307218.A patent/NL160259C/en not_active IP Right Cessation
- 1973-05-23 NO NO2120/73A patent/NO140268C/en unknown
- 1973-05-23 FR FR7318733A patent/FR2185625B1/fr not_active Expired
- 1973-05-24 CH CH747673A patent/CH583506A5/xx not_active IP Right Cessation
- 1973-05-24 YU YU01370/73A patent/YU137073A/en unknown
- 1973-05-24 IT IT24541/73A patent/IT987878B/en active
- 1973-06-04 MX MX143886A patent/MX147114A/en unknown
- 1973-12-07 NO NO4674/73A patent/NO141300C/en unknown
-
1975
- 1975-09-16 ES ES441014A patent/ES441014A1/en not_active Expired
-
1976
- 1976-06-24 JP JP51073894A patent/JPS527980A/en active Pending
-
1978
- 1978-06-13 KE KE2845A patent/KE2845A/en unknown
- 1978-06-22 HK HK313/78A patent/HK31378A/en unknown
- 1978-12-31 MY MY1978316A patent/MY7800316A/en unknown
-
1979
- 1979-06-29 YU YU01563/79A patent/YU156379A/en unknown
- 1979-06-29 YU YU01562/79A patent/YU156279A/en unknown
- 1979-06-29 YU YU01564/79A patent/YU156479A/en unknown
- 1979-06-29 YU YU01566/79A patent/YU156679A/en unknown
- 1979-06-29 YU YU01561/79A patent/YU156179A/en unknown
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