CH557828A - Verfahren zur herstellung substituierter phthalimido-1,3,5triazine. - Google Patents
Verfahren zur herstellung substituierter phthalimido-1,3,5triazine.Info
- Publication number
- CH557828A CH557828A CH1676070A CH1676070A CH557828A CH 557828 A CH557828 A CH 557828A CH 1676070 A CH1676070 A CH 1676070A CH 1676070 A CH1676070 A CH 1676070A CH 557828 A CH557828 A CH 557828A
- Authority
- CH
- Switzerland
- Prior art keywords
- phthalimido
- triazine
- mol
- chloro
- chloride
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- 150000003973 alkyl amines Chemical class 0.000 claims description 8
- 239000005457 ice water Substances 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- SPAZWLWQEDJMAW-UHFFFAOYSA-N 2-(4,6-dichloro-1,3,5-triazin-2-yl)isoindole-1,3-dione Chemical compound ClC1=NC(Cl)=NC(N2C(C3=CC=CC=C3C2=O)=O)=N1 SPAZWLWQEDJMAW-UHFFFAOYSA-N 0.000 claims description 7
- ILGOUVXDTDKOAN-UHFFFAOYSA-N 2-[4-chloro-6-(1,3-dioxoisoindol-2-yl)-1,3,5-triazin-2-yl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1=NC(N2C(C3=CC=CC=C3C2=O)=O)=NC(Cl)=N1 ILGOUVXDTDKOAN-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000005544 phthalimido group Chemical group 0.000 claims description 7
- BAXKFBIHLQGUBU-UHFFFAOYSA-N 2-[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]isoindole-1,3-dione Chemical compound C(C)NC1=NC(=NC(=N1)N1C(C=2C(C1=O)=CC=CC2)=O)Cl BAXKFBIHLQGUBU-UHFFFAOYSA-N 0.000 claims description 6
- 241000196324 Embryophyta Species 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- YXYAWRUGUHOBFC-UHFFFAOYSA-N 2-[4,6-bis(1,3-dioxoisoindol-2-yl)-1,3,5-triazin-2-yl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1=NC(N2C(C3=CC=CC=C3C2=O)=O)=NC(N2C(C3=CC=CC=C3C2=O)=O)=N1 YXYAWRUGUHOBFC-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- 240000008042 Zea mays Species 0.000 claims description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 claims description 4
- -1 phthalimide alkali metal Chemical class 0.000 claims description 4
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 3
- 235000009973 maize Nutrition 0.000 claims description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 231100000208 phytotoxic Toxicity 0.000 claims description 2
- 230000000885 phytotoxic effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical class COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- LNSAEWXPCBLGDX-UHFFFAOYSA-M sodium;2-(2,4-dichlorophenoxy)acetate;hydrate Chemical compound O.[Na+].[O-]C(=O)COC1=CC=C(Cl)C=C1Cl LNSAEWXPCBLGDX-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB5344070A GB1324718A (en) | 1970-11-10 | 1970-11-10 | Phthalimido triazines |
CH1410574A CH564551A5 (ru) | 1970-11-10 | 1970-11-12 | |
CH1676070A CH557828A (de) | 1970-11-10 | 1970-11-12 | Verfahren zur herstellung substituierter phthalimido-1,3,5triazine. |
CS74547A CS165316B2 (en) | 1970-11-10 | 1970-11-16 | Method of substituted phthalimide-1,3,5-triazines production |
CS74548A CS165317B2 (en) | 1970-11-10 | 1970-11-16 | Method of substituted phthalimide-1,3,5-triazines production |
SU701495559D SU452962A3 (ru) | 1970-11-10 | 1970-11-17 | Способ получени фталимидо-1,3,5триазинов |
SU1495559A SU429583A3 (ru) | 1970-11-10 | 1970-11-17 | |
SU1766767A SU437297A3 (ru) | 1970-11-10 | 1970-11-17 | Способ получения фталимидо-1,3,5-триазинов |
NL7017108A NL7017108A (ru) | 1970-11-10 | 1970-11-23 | |
FR7042588A FR2115622A5 (ru) | 1970-11-10 | 1970-11-26 | |
BE759524D BE759524A (en) | 1970-11-10 | 1970-11-27 | Herbicidal phthalimido - 1,3,5-triazine derivs |
US00098026A US3794641A (en) | 1970-11-10 | 1970-12-14 | Substituted phthalimido-1,3,5-triazines |
CH1676070A CH583210A5 (ru) | 1970-11-10 | 1975-04-17 |
Applications Claiming Priority (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB5344070 | 1970-11-10 | ||
CH1410574A CH564551A5 (ru) | 1970-11-10 | 1970-11-12 | |
CH1676070A CH557828A (de) | 1970-11-10 | 1970-11-12 | Verfahren zur herstellung substituierter phthalimido-1,3,5triazine. |
CS74547A CS165316B2 (en) | 1970-11-10 | 1970-11-16 | Method of substituted phthalimide-1,3,5-triazines production |
CS74548A CS165317B2 (en) | 1970-11-10 | 1970-11-16 | Method of substituted phthalimide-1,3,5-triazines production |
SU1495559A SU429583A3 (ru) | 1970-11-10 | 1970-11-17 | |
SU1766767A SU437297A3 (ru) | 1970-11-10 | 1970-11-17 | Способ получения фталимидо-1,3,5-триазинов |
NL7017108A NL7017108A (ru) | 1970-11-10 | 1970-11-23 | |
FR7042588A FR2115622A5 (ru) | 1970-11-10 | 1970-11-26 | |
BE759524 | 1970-11-27 | ||
US9802670A | 1970-12-14 | 1970-12-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH557828A true CH557828A (de) | 1975-01-15 |
Family
ID=34109346
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1410574A CH564551A5 (ru) | 1970-11-10 | 1970-11-12 | |
CH1676070A CH557828A (de) | 1970-11-10 | 1970-11-12 | Verfahren zur herstellung substituierter phthalimido-1,3,5triazine. |
CH1676070A CH583210A5 (ru) | 1970-11-10 | 1975-04-17 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1410574A CH564551A5 (ru) | 1970-11-10 | 1970-11-12 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1676070A CH583210A5 (ru) | 1970-11-10 | 1975-04-17 |
Country Status (8)
Country | Link |
---|---|
US (1) | US3794641A (ru) |
BE (1) | BE759524A (ru) |
CH (3) | CH564551A5 (ru) |
CS (2) | CS165317B2 (ru) |
FR (1) | FR2115622A5 (ru) |
GB (1) | GB1324718A (ru) |
NL (1) | NL7017108A (ru) |
SU (3) | SU452962A3 (ru) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3896224A (en) * | 1972-04-10 | 1975-07-22 | Ciba Geigy Corp | 1-(4',6'-dichloro-s-triazin-2-ylcarbamoyl)-2-methoxy- carbonylamino-benzimidazole |
EP0885214A1 (en) * | 1996-03-01 | 1998-12-23 | Cytec Technology Corp. | Cyclic imido-1,3,5-triazine crosslinking agents |
WO2002068414A2 (en) * | 2001-02-27 | 2002-09-06 | The Governement Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services | Analogs of thalidomide as potential angiogenesis inhibitors |
AT410797B (de) * | 2001-07-26 | 2003-07-25 | Agrolinz Melamin Gmbh | Imidotriazinderivate |
US8952895B2 (en) | 2011-06-03 | 2015-02-10 | Apple Inc. | Motion-based device operations |
CA2808646C (en) * | 2003-09-17 | 2016-08-23 | The Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services | Thalidomide analogs as tnf-alpha modulators |
AU2007238785B2 (en) * | 2006-04-13 | 2013-02-07 | Agnieszka Ambrozak | Tetrahalogenated compounds useful as inhibitors of angiogenesis |
MX2008014972A (es) * | 2006-05-22 | 2009-04-15 | Univ New York | C-glucolipidos con perfil de th-1 mejorado. |
US8415470B2 (en) | 2011-06-24 | 2013-04-09 | E I Du Pont De Nemours And Company | Di-isoimide composition |
US8586734B2 (en) | 2011-06-24 | 2013-11-19 | E I Du Pont De Nemours And Company | Process for preparing substituted and unsubstituted diamino triazine aromatic di-isoimides |
US8536170B2 (en) | 2011-06-24 | 2013-09-17 | E I Du Pont De Nemours And Company | Curable composition comprising a di-isoimide, method of curing, and the cured composition so formed |
US8927725B2 (en) | 2011-12-02 | 2015-01-06 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Thio compounds |
CN105330650B (zh) * | 2015-11-04 | 2018-01-02 | 中北大学 | 一种非极性改性三聚氰胺基阻燃剂的制备方法及应用 |
CN106866636B (zh) * | 2016-12-27 | 2019-09-03 | 中国石油天然气股份有限公司 | 一种亚酰胺类β晶型成核剂及其制备方法与应用 |
-
1970
- 1970-11-10 GB GB5344070A patent/GB1324718A/en not_active Expired
- 1970-11-12 CH CH1410574A patent/CH564551A5/de not_active IP Right Cessation
- 1970-11-12 CH CH1676070A patent/CH557828A/de not_active IP Right Cessation
- 1970-11-16 CS CS74548A patent/CS165317B2/cs unknown
- 1970-11-16 CS CS74547A patent/CS165316B2/cs unknown
- 1970-11-17 SU SU701495559D patent/SU452962A3/ru active
- 1970-11-17 SU SU1495559A patent/SU429583A3/ru active
- 1970-11-17 SU SU1766767A patent/SU437297A3/ru active
- 1970-11-23 NL NL7017108A patent/NL7017108A/xx unknown
- 1970-11-26 FR FR7042588A patent/FR2115622A5/fr not_active Expired
- 1970-11-27 BE BE759524D patent/BE759524A/xx unknown
- 1970-12-14 US US00098026A patent/US3794641A/en not_active Expired - Lifetime
-
1975
- 1975-04-17 CH CH1676070A patent/CH583210A5/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
SU437297A3 (ru) | 1974-07-25 |
CH583210A5 (ru) | 1976-12-31 |
GB1324718A (en) | 1973-07-25 |
CS165317B2 (en) | 1975-12-22 |
US3794641A (en) | 1974-02-26 |
SU429583A3 (ru) | 1974-05-25 |
SU452962A3 (ru) | 1974-12-05 |
BE759524A (en) | 1971-04-30 |
NL7017108A (ru) | 1972-05-25 |
CS165316B2 (en) | 1975-12-22 |
CH564551A5 (ru) | 1975-07-31 |
FR2115622A5 (ru) | 1972-07-07 |
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Legal Events
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PL | Patent ceased |