IL42103A - 6-amino-s-triazine-2,4-(1h,3h)-diones and corresponding 4-thio compounds,their preparation and their use as herbicides - Google Patents
6-amino-s-triazine-2,4-(1h,3h)-diones and corresponding 4-thio compounds,their preparation and their use as herbicidesInfo
- Publication number
- IL42103A IL42103A IL42103A IL4210373A IL42103A IL 42103 A IL42103 A IL 42103A IL 42103 A IL42103 A IL 42103A IL 4210373 A IL4210373 A IL 4210373A IL 42103 A IL42103 A IL 42103A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- methyl
- formula
- alkyl
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000004009 herbicide Substances 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 40
- 150000001875 compounds Chemical class 0.000 claims abstract 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract 26
- -1 trimethylcyclohexyl Chemical group 0.000 claims abstract 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 239000001257 hydrogen Substances 0.000 claims abstract 14
- 150000001412 amines Chemical class 0.000 claims abstract 8
- 150000002431 hydrogen Chemical group 0.000 claims abstract 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 7
- 239000000460 chlorine Substances 0.000 claims abstract 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 239000001301 oxygen Substances 0.000 claims abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 4
- 239000002585 base Substances 0.000 claims abstract 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 2
- 239000002168 alkylating agent Substances 0.000 claims abstract 2
- 229940100198 alkylating agent Drugs 0.000 claims abstract 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract 2
- 150000001768 cations Chemical class 0.000 claims abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims abstract 2
- 239000011737 fluorine Chemical group 0.000 claims abstract 2
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 239000012948 isocyanate Substances 0.000 claims abstract 2
- 150000002513 isocyanates Chemical class 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 34
- 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 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 13
- 238000004519 manufacturing process Methods 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 5
- 229910052717 sulfur Chemical group 0.000 claims 5
- 239000011593 sulfur Chemical group 0.000 claims 5
- 239000012876 carrier material Substances 0.000 claims 4
- 235000017168 chlorine Nutrition 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000004094 surface-active agent Substances 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical class Cl* 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- NILOACNZUNQORM-UHFFFAOYSA-N methyl n-cyano-n-methylcarbamate Chemical compound COC(=O)N(C)C#N NILOACNZUNQORM-UHFFFAOYSA-N 0.000 claims 1
- 239000012022 methylating agents Substances 0.000 claims 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- YSKUZVBSHIWEFK-UHFFFAOYSA-N ammelide Chemical class NC1=NC(O)=NC(O)=N1 YSKUZVBSHIWEFK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001805 chlorine compounds Chemical group 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
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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 |
|---|---|
| IL42103A0 IL42103A0 (en) | 1973-06-29 |
| IL42103A true IL42103A (en) | 1976-05-31 |
Family
ID=27400932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42103A IL42103A (en) | 1972-05-24 | 1973-04-25 | 6-amino-s-triazine-2,4-(1h,3h)-diones and corresponding 4-thio compounds,their preparation and their use as herbicides |
Country Status (30)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS602306B2 (ja) * | 1972-11-06 | 1985-01-21 | バイエル アクチエンゲゼルシヤフト | テトラヒドロ−１，３，５−トリアジン−２，６−ジオン類の製造方法 |
| DE2254200C2 (de) * | 1972-11-06 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | Tetrahydro-1,3,5-triazin-2,6-dione, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide |
| 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 |
| BR7602779A (pt) * | 1975-05-05 | 1976-11-09 | Du Pont | Processo para a preparacao de triazinas herbicidas |
| 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 |
| IL305234A (en) * | 2021-03-17 | 2023-10-01 | Hansoh Bio Llc | Nitrogen-containing heterocyclic ketones, preparation methods and medicinal uses thereof |
| AU2023270440A1 (en) * | 2022-05-20 | 2024-12-19 | 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/xx unknown
- 1973-05-15 IE IE762/73A patent/IE37629B1/xx unknown
- 1973-05-16 AR AR248054A patent/AR213607A1/es active
- 1973-05-17 OA OA54914A patent/OA04410A/xx unknown
- 1973-05-22 DD DD179515*A patent/DD112651A5/xx unknown
- 1973-05-22 DD DD170989A patent/DD106938A5/xx unknown
- 1973-05-22 BG BG023690A patent/BG22363A3/xx unknown
- 1973-05-22 EG EG189/73A patent/EG10976A/xx active
- 1973-05-22 JP JP5642873A patent/JPS5418339B2/ja not_active Expired
- 1973-05-23 CY CY972A patent/CY972A/xx unknown
- 1973-05-23 DK DK283473AA patent/DK139911B/da not_active IP Right Cessation
- 1973-05-23 HU HUDU203A patent/HU167436B/hu unknown
- 1973-05-23 RO RO7383863A patent/RO68557A/ro unknown
- 1973-05-23 NL NL7307218.A patent/NL160259C/xx not_active IP Right Cessation
- 1973-05-23 SU SU731923101A patent/SU616994A3/ru active
- 1973-05-23 DE DE2326358A patent/DE2326358C3/de not_active Expired
- 1973-05-23 NO NO2120/73A patent/NO140268C/no unknown
- 1973-05-23 LU LU67653A patent/LU67653A1/xx unknown
- 1973-05-23 FI FI1667/73A patent/FI57940C/fi active
- 1973-05-23 FR FR7318733A patent/FR2185625B1/fr not_active Expired
- 1973-05-23 GB GB2467773A patent/GB1435585A/en not_active Expired
- 1973-05-23 RO RO74881A patent/RO71605B/ro unknown
- 1973-05-24 IT IT24541/73A patent/IT987878B/it active
- 1973-05-24 CH CH747673A patent/CH583506A5/xx not_active IP Right Cessation
- 1973-05-24 YU YU01370/73A patent/YU137073A/xx unknown
- 1973-06-04 MX MX143886A patent/MX147114A/es unknown
- 1973-12-07 NO NO4674/73A patent/NO141300C/no unknown
-
1975
- 1975-09-16 ES ES441014A patent/ES441014A1/es not_active Expired
-
1976
- 1976-06-24 JP JP51073894A patent/JPS527980A/ja active Pending
-
1978
- 1978-06-13 KE KE2845A patent/KE2845A/xx unknown
- 1978-06-22 HK HK313/78A patent/HK31378A/xx unknown
- 1978-12-31 MY MY1978316A patent/MY7800316A/xx unknown
-
1979
- 1979-06-29 YU YU01564/79A patent/YU156479A/xx unknown
- 1979-06-29 YU YU01566/79A patent/YU156679A/xx unknown
- 1979-06-29 YU YU01563/79A patent/YU156379A/xx unknown
- 1979-06-29 YU YU01562/79A patent/YU156279A/xx unknown
- 1979-06-29 YU YU01561/79A patent/YU156179A/xx unknown
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