DE2425287A1 - Triazinderivate - Google Patents
TriazinderivateInfo
- Publication number
- DE2425287A1 DE2425287A1 DE19742425287 DE2425287A DE2425287A1 DE 2425287 A1 DE2425287 A1 DE 2425287A1 DE 19742425287 DE19742425287 DE 19742425287 DE 2425287 A DE2425287 A DE 2425287A DE 2425287 A1 DE2425287 A1 DE 2425287A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- group
- chlorine atom
- triazine
- 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.)
- Pending
Links
- 150000003918 triazines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 19
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- 239000004009 herbicide Substances 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- -1 methylthiocyanuric dichloride Chemical compound 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LTQATLDCNDGNTO-UHFFFAOYSA-N 1,3,5-tris(2-methylpropyl)triazinane Chemical compound CC(C)CC1CN(CC(C)C)NN(CC(C)C)C1 LTQATLDCNDGNTO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical compound C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- TWWNLDITIRCJDN-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)naphthalene;sodium Chemical compound [Na].C1=CC=CC2=C(CC(C)C)C(CC(C)C)=CC=C21 TWWNLDITIRCJDN-UHFFFAOYSA-N 0.000 description 1
- MWPZLWRHHPWTFS-UHFFFAOYSA-N 2,4-dichloro-6-methylsulfanyl-1,3,5-triazine Chemical compound CSC1=NC(Cl)=NC(Cl)=N1 MWPZLWRHHPWTFS-UHFFFAOYSA-N 0.000 description 1
- WBEKRMVYCWRRDJ-UHFFFAOYSA-N 2-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound CC(C)NC1=NC=NC(N)=N1 WBEKRMVYCWRRDJ-UHFFFAOYSA-N 0.000 description 1
- JDAPQMINSZDTBM-UHFFFAOYSA-N 4,6-dichloro-n-propan-2-yl-1,3,5-triazin-2-amine Chemical compound CC(C)NC1=NC(Cl)=NC(Cl)=N1 JDAPQMINSZDTBM-UHFFFAOYSA-N 0.000 description 1
- ULVNIJSKNRGBHX-UHFFFAOYSA-N 4-chloro-1,3,5-triazin-2-amine Chemical compound NC1=NC=NC(Cl)=N1 ULVNIJSKNRGBHX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- CXDBXTHJTZQPOJ-UHFFFAOYSA-M [Na+].CC=C.CC=C.CC=C.CC=C.[O-]S(=O)(=O)C1=CC=CC=C1 Chemical compound [Na+].CC=C.CC=C.CC=C.CC=C.[O-]S(=O)(=O)C1=CC=CC=C1 CXDBXTHJTZQPOJ-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 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
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
-
- 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
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742425287 DE2425287A1 (de) | 1974-05-24 | 1974-05-24 | Triazinderivate |
| US05/579,015 US4021424A (en) | 1974-05-24 | 1975-05-19 | S-triazines |
| GB2283675A GB1463028A (en) | 1974-05-24 | 1975-05-23 | Substituted amino-s-triazines and their use in herbicidal compositions |
| IL47345A IL47345A0 (en) | 1974-05-24 | 1975-05-23 | Novel s-triazine derivatives,their preparation and herbicidal compositions containing them |
| BE156658A BE829430A (fr) | 1974-05-24 | 1975-05-23 | Derives de triazines |
| NL7506073A NL7506073A (nl) | 1974-05-24 | 1975-05-23 | Werkwijze ter bereiding van nieuwe triazine- derivaten. |
| FR7516158A FR2272088B1 (OSRAM) | 1974-05-24 | 1975-05-23 | |
| JP50062425A JPS5123277A (OSRAM) | 1974-05-24 | 1975-05-24 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742425287 DE2425287A1 (de) | 1974-05-24 | 1974-05-24 | Triazinderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2425287A1 true DE2425287A1 (de) | 1975-12-11 |
Family
ID=5916425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742425287 Pending DE2425287A1 (de) | 1974-05-24 | 1974-05-24 | Triazinderivate |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4021424A (OSRAM) |
| JP (1) | JPS5123277A (OSRAM) |
| BE (1) | BE829430A (OSRAM) |
| DE (1) | DE2425287A1 (OSRAM) |
| FR (1) | FR2272088B1 (OSRAM) |
| GB (1) | GB1463028A (OSRAM) |
| IL (1) | IL47345A0 (OSRAM) |
| NL (1) | NL7506073A (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0073974A3 (de) * | 1981-08-29 | 1983-11-16 | Bayer Ag | Fluorhaltige 4,6-Diamino-s-triazine, Verfahren und neue Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Herbizide |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4155920A (en) * | 1977-04-04 | 1979-05-22 | The Standard Oil Company | Synthesis of maleic anhydride |
| US11192883B2 (en) | 2018-10-26 | 2021-12-07 | University Of South Alabama | Functionalized materials and compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732220A (en) * | 1970-10-16 | 1973-05-08 | Allied Chem | Chloro-n,n-disubstituted amino methylene amino-s-triazines |
-
1974
- 1974-05-24 DE DE19742425287 patent/DE2425287A1/de active Pending
-
1975
- 1975-05-19 US US05/579,015 patent/US4021424A/en not_active Expired - Lifetime
- 1975-05-23 NL NL7506073A patent/NL7506073A/xx not_active Application Discontinuation
- 1975-05-23 IL IL47345A patent/IL47345A0/xx unknown
- 1975-05-23 BE BE156658A patent/BE829430A/xx unknown
- 1975-05-23 FR FR7516158A patent/FR2272088B1/fr not_active Expired
- 1975-05-23 GB GB2283675A patent/GB1463028A/en not_active Expired
- 1975-05-24 JP JP50062425A patent/JPS5123277A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0073974A3 (de) * | 1981-08-29 | 1983-11-16 | Bayer Ag | Fluorhaltige 4,6-Diamino-s-triazine, Verfahren und neue Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Herbizide |
| US4459151A (en) * | 1981-08-29 | 1984-07-10 | Bayer Aktiengesellschaft | Herbicidally active fluorine-containing 4,6-diamino-s-triazines |
Also Published As
| Publication number | Publication date |
|---|---|
| BE829430A (fr) | 1975-11-24 |
| IL47345A0 (en) | 1975-07-28 |
| JPS5123277A (OSRAM) | 1976-02-24 |
| FR2272088B1 (OSRAM) | 1979-03-30 |
| NL7506073A (nl) | 1975-11-26 |
| FR2272088A1 (OSRAM) | 1975-12-19 |
| US4021424A (en) | 1977-05-03 |
| GB1463028A (en) | 1977-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |