DE2416930C2 - Verfahren zur Herstellung von substituierten 2-Chlor-4-alkylamino-6-(1-cyanalkylamino)-1,3,5-triazinen - Google Patents
Verfahren zur Herstellung von substituierten 2-Chlor-4-alkylamino-6-(1-cyanalkylamino)-1,3,5-triazinenInfo
- Publication number
- DE2416930C2 DE2416930C2 DE19742416930 DE2416930A DE2416930C2 DE 2416930 C2 DE2416930 C2 DE 2416930C2 DE 19742416930 DE19742416930 DE 19742416930 DE 2416930 A DE2416930 A DE 2416930A DE 2416930 C2 DE2416930 C2 DE 2416930C2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- ketone
- solution
- acetone
- aminonitrile
- 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
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000000243 solution Substances 0.000 claims description 35
- 150000002576 ketones Chemical class 0.000 claims description 24
- 239000007864 aqueous solution Substances 0.000 claims description 19
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 125000005219 aminonitrile group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- -1 alkali metal cyanide Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000010626 work up procedure Methods 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 7
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MZZBPDKVEFVLFF-UHFFFAOYSA-N Cyanazine Natural products CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- IUCVBFHDSFSEIK-UHFFFAOYSA-N 2-{[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino}-2-methylbutanenitrile Chemical compound CCNC1=NC(Cl)=NC(NC(C)(CC)C#N)=N1 IUCVBFHDSFSEIK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- YJEOYSMFPMVDLB-UHFFFAOYSA-N N#CN.CC(=O)C Chemical compound N#CN.CC(=O)C YJEOYSMFPMVDLB-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
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- VVXOSJUBBAUVMI-UHFFFAOYSA-N propan-2-one;2,4,6-trichloro-1,3,5-triazine Chemical compound CC(C)=O.ClC1=NC(Cl)=NC(Cl)=N1 VVXOSJUBBAUVMI-UHFFFAOYSA-N 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUNO000172 HU167030B (enExample) | 1973-04-09 | 1973-04-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2416930A1 DE2416930A1 (de) | 1974-10-24 |
| DE2416930C2 true DE2416930C2 (de) | 1984-08-30 |
Family
ID=11000028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742416930 Expired DE2416930C2 (de) | 1973-04-09 | 1974-04-08 | Verfahren zur Herstellung von substituierten 2-Chlor-4-alkylamino-6-(1-cyanalkylamino)-1,3,5-triazinen |
Country Status (10)
| Country | Link |
|---|---|
| CS (1) | CS203971B2 (enExample) |
| DE (1) | DE2416930C2 (enExample) |
| ES (1) | ES447118A1 (enExample) |
| FR (1) | FR2224467A1 (enExample) |
| HU (1) | HU167030B (enExample) |
| PL (1) | PL99093B1 (enExample) |
| RO (2) | RO63907A (enExample) |
| SU (1) | SU598560A3 (enExample) |
| TR (1) | TR17906A (enExample) |
| YU (2) | YU39918B (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH550546A (de) * | 1971-08-05 | 1974-06-28 | Ciba Geigy Ag | Herbizides mittel. |
-
1973
- 1973-04-09 HU HUNO000172 patent/HU167030B/hu not_active IP Right Cessation
-
1974
- 1974-04-05 YU YU95474A patent/YU39918B/xx unknown
- 1974-04-05 FR FR7412077A patent/FR2224467A1/fr active Granted
- 1974-04-08 DE DE19742416930 patent/DE2416930C2/de not_active Expired
- 1974-04-08 CS CS251874A patent/CS203971B2/cs unknown
- 1974-04-08 SU SU742017401A patent/SU598560A3/ru active
- 1974-04-09 RO RO7835674A patent/RO63907A/ro unknown
- 1974-04-09 TR TR1790674A patent/TR17906A/xx unknown
- 1974-04-09 RO RO7484992A patent/RO70194A/ro unknown
- 1974-04-09 PL PL18347274A patent/PL99093B1/pl unknown
-
1976
- 1976-04-15 ES ES447118A patent/ES447118A1/es not_active Expired
-
1980
- 1980-04-01 YU YU90380A patent/YU40071B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO63907A (fr) | 1978-09-15 |
| RO70194A (ro) | 1980-12-30 |
| PL99093B1 (pl) | 1978-06-30 |
| YU90380A (en) | 1983-02-28 |
| DE2416930A1 (de) | 1974-10-24 |
| HU167030B (enExample) | 1975-07-28 |
| YU95474A (en) | 1982-06-30 |
| TR17906A (tr) | 1976-11-01 |
| CS203971B2 (en) | 1981-03-31 |
| FR2224467A1 (en) | 1974-10-31 |
| YU39918B (en) | 1985-06-30 |
| FR2224467B1 (enExample) | 1978-01-13 |
| YU40071B (en) | 1985-06-30 |
| SU598560A3 (ru) | 1978-03-15 |
| ES447118A1 (es) | 1977-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8381 | Inventor (new situation) |
Free format text: BORDAS, BARNA, BUDAPEST, HU CEKMANY, ARNOLD, BALATONALMADI, HU DAMJAN, GEB. PINTER, KORNELIA HORVAT, ANDRAS HUSZAK, GYOERGY, FUEZFOEGYARTELEP, HU KOLONICS, ZOLTAN, BALATONALMADI, HU MATOLCSY, GYOERGY, DR., BUDAPEST, HU NAGY, GEB. PAGAI, MARIA, VESZPREM, HU PELYVA, JENOE SZERTICS, JOZSEF, FUEZFOEGYARTELEP, HU |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |