CA1061354A - 3-cyanamino-2,6-dinitroanilines - Google Patents
3-cyanamino-2,6-dinitroanilinesInfo
- Publication number
- CA1061354A CA1061354A CA254,928A CA254928A CA1061354A CA 1061354 A CA1061354 A CA 1061354A CA 254928 A CA254928 A CA 254928A CA 1061354 A CA1061354 A CA 1061354A
- Authority
- CA
- Canada
- Prior art keywords
- cyanamino
- dinitro
- chloro
- trifluoromethylaniline
- triethylamine salt
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- -1 alkali metal salts Chemical class 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 241000233679 Peronosporaceae Species 0.000 abstract description 5
- 235000009754 Vitis X bourquina Nutrition 0.000 abstract description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 abstract description 3
- 235000014787 Vitis vinifera Nutrition 0.000 abstract description 3
- FDSBMUJBQJNCNW-UHFFFAOYSA-N 3-chloro-2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC(Cl)=C1[N+]([O-])=O FDSBMUJBQJNCNW-UHFFFAOYSA-N 0.000 abstract description 2
- 241001281803 Plasmopara viticola Species 0.000 abstract description 2
- 240000006365 Vitis vinifera Species 0.000 abstract 1
- 231100000676 disease causative agent Toxicity 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 17
- 239000002270 dispersing agent Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000428 dust Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000219095 Vitis Species 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052903 pyrophyllite Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
- DPQYRXNRGNLPFC-UHFFFAOYSA-N 2,4-dichloro-1,3-dinitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1Cl DPQYRXNRGNLPFC-UHFFFAOYSA-N 0.000 description 1
- DIEWCWYPWAGPFZ-UHFFFAOYSA-N CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O DIEWCWYPWAGPFZ-UHFFFAOYSA-N 0.000 description 1
- YPGYIKOXQRDUSU-UHFFFAOYSA-N CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O YPGYIKOXQRDUSU-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- IBORVNWWBXIDQY-UHFFFAOYSA-N [2,4-dinitro-3-(pentan-3-ylamino)-6-(trifluoromethyl)phenyl]cyanamide Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C(F)(F)F)C(NC#N)=C1[N+]([O-])=O IBORVNWWBXIDQY-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- KXHORCXSQZTQQI-UHFFFAOYSA-N n-(fluoromethyl)aniline Chemical compound FCNC1=CC=CC=C1 KXHORCXSQZTQQI-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C261/00—Derivatives of cyanic acid
- C07C261/04—Cyanamides
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/589,313 US3979453A (en) | 1975-06-23 | 1975-06-23 | 3-Cyanamino-2,6-dinitroanilines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1061354A true CA1061354A (en) | 1979-08-28 |
Family
ID=24357484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,928A Expired CA1061354A (en) | 1975-06-23 | 1976-06-16 | 3-cyanamino-2,6-dinitroanilines |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3979453A (forum.php) |
| CA (1) | CA1061354A (forum.php) |
| CS (1) | CS189798B2 (forum.php) |
| ES (1) | ES460762A1 (forum.php) |
| IN (1) | IN144222B (forum.php) |
| SU (1) | SU644375A3 (forum.php) |
| ZA (1) | ZA763547B (forum.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4430114A (en) | 1979-07-25 | 1984-02-07 | American Cyanamid Company | 2,6-Dinitroaniline herbicides, and use thereof |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2212825A (en) * | 1937-12-31 | 1940-08-27 | Du Pont | Nitro-trifluoromethyl-aryl amines and process for making them |
| NL132336C (forum.php) * | 1951-01-28 | |||
| DE2037265A1 (de) * | 1970-07-28 | 1972-02-03 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Herbizid |
| US3111403A (en) * | 1960-08-31 | 1963-11-19 | Lilly Co Eli | Herbicidal method |
| US3257190A (en) * | 1962-12-10 | 1966-06-21 | Lilly Co Eli | Method of eliminating weed grasses and broadleaf weeds |
| US3332769A (en) * | 1963-10-07 | 1967-07-25 | Lilly Co Eli | Method of eliminating germinating and seedling weed grasses and broadleaf weeds |
| US3227734A (en) * | 1964-11-13 | 1966-01-04 | Shell Oil Co | Herbicidal 4-methylsulfonyl-2,6-dinitro-n,n-substituted anilines |
| US3617252A (en) * | 1969-04-01 | 1971-11-02 | United States Borax Chem | Herbicidal dinitro-1,3-phenylenediamine compounds |
| DE1950601A1 (de) * | 1969-10-08 | 1971-04-15 | Basf Ag | Herbizid |
| US3617251A (en) * | 1969-11-10 | 1971-11-02 | United States Borax Chem | Herbicidal halodinitro-1,3-phenylenediamine compounds |
| DE2009497A1 (de) * | 1970-02-28 | 1971-09-09 | Farbenfabriken Bayer Aktiengesell schaft, 5090 Leverkusen | Substituierte 6 Nitroanihn Derivate, Verfahren zu ihrer Herstellung und ihre Ver Wendung als herbizide Mittel |
| US3672864A (en) * | 1970-06-11 | 1972-06-27 | Exxon Research Engineering Co | Control of pests with cycloalkane derivatives of nitrated aryl compounds |
| US3764624A (en) * | 1970-08-05 | 1973-10-09 | United States Borax Chem | N-substituted-2,6-dinitro-3-(alkoxy or alkylthio)-4-substituted-aniline compounds |
| US3910783A (en) * | 1970-11-02 | 1975-10-07 | United States Borax Chem | Dinitro-1,3-p |
| US3672866A (en) * | 1970-11-12 | 1972-06-27 | Amchem Prod | Use of n-(sec-butyl)-4-(t-butyl)-2,6-dinitroaniline as a selective herbicide |
| US3888897A (en) * | 1972-04-12 | 1975-06-10 | Du Pont | Cyano-and cyanomethyl-benzensulfonamides |
| GB1442512A (en) | 1973-06-25 | 1976-07-14 | American Cyanamid Co | Preparation of 2,6-dinitroanilines |
-
1975
- 1975-06-23 US US05/589,313 patent/US3979453A/en not_active Expired - Lifetime
-
1976
- 1976-06-15 CS CS777982A patent/CS189798B2/cs unknown
- 1976-06-15 IN IN1040/CAL/76A patent/IN144222B/en unknown
- 1976-06-15 ZA ZA00763547A patent/ZA763547B/xx unknown
- 1976-06-16 CA CA254,928A patent/CA1061354A/en not_active Expired
-
1977
- 1977-07-14 ES ES460762A patent/ES460762A1/es not_active Expired
- 1977-09-21 SU SU772522953A patent/SU644375A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| US3979453A (en) | 1976-09-07 |
| CS189798B2 (en) | 1979-04-30 |
| SU644375A3 (ru) | 1979-01-25 |
| IN144222B (forum.php) | 1978-04-08 |
| ES460762A1 (es) | 1978-05-01 |
| ZA763547B (en) | 1978-01-25 |
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