GB919458A - Carbamyl and thiocarbamyl substances, methods for producing same and applications thereof - Google Patents
Carbamyl and thiocarbamyl substances, methods for producing same and applications thereofInfo
- Publication number
- GB919458A GB919458A GB921359A GB921359A GB919458A GB 919458 A GB919458 A GB 919458A GB 921359 A GB921359 A GB 921359A GB 921359 A GB921359 A GB 921359A GB 919458 A GB919458 A GB 919458A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- alkyl
- compounds
- aminotriazole
- reacting
- 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 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title 1
- 239000000126 substance Substances 0.000 title 1
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000005059 halophenyl group Chemical group 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 abstract 2
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 abstract 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises compounds of formula <FORM:0919458/IV (b)/1> where X is oxygen or sulphur, R is hydrogen or C1-4 alkyl, R1 is hydrogen, and R2 and R3 are hydrogen, C1-18 alkyl or alkenyl, phenyl or halophenyl. Compounds in which R2 is hydrogen are prepared by reacting a solution of an aminotriazole with R3NCX; those in which R2 and R3 are hydrogen, by reacting aminoguanidine bicarbonate with formic, acetic, propionic or butyric acid or other alkanoic acid and further reacting with potassium cyanate in the presence of a mineral acid. Other methods illustrated in the examples are the reaction of 3-aminotriazole-1,2,4 or 3-amino-5-methyltriazole-1,2,4 with potassium cyanate in the presence of a mineral acid, and the reaction between 3-aminotriazole-1,2,4 and dimethylcarbamyl chloride. The compounds of the invention are of use as fungicides and herbicides (see Group VI).ALSO:Fungicidal or herbicidal compositions comprise compounds of formula <FORM:0919458/VI/1> where X is oxygen or sulphur, R is hydrogen or C1-4 alkyl, R1 is hydrogen, and R2 and R3 are hydrogen C1-18, alkyl or alkenyl, phenyl or halophenyl (see Group IV (b)), singly or in admixture, with or without fillers, or as an emulsion or suspension in a liquid.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR760758 | 1958-03-17 | ||
| FR785788A FR1421202A (en) | 1959-02-04 | 1959-02-04 | Process for the manufacture of (1,2,4-triazolyl) -urea and analogous compounds |
| FR785787A FR1425253A (en) | 1959-02-04 | 1959-02-04 | New fungicidal compounds, in particular thioureas substituted by a thiazole group 1, 2, 4, and their manufacturing processes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB919458A true GB919458A (en) | 1963-02-27 |
Family
ID=27245151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB921359A Expired GB919458A (en) | 1958-03-17 | 1959-03-17 | Carbamyl and thiocarbamyl substances, methods for producing same and applications thereof |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE576586A (en) |
| GB (1) | GB919458A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3308131A (en) * | 1962-12-06 | 1967-03-07 | Du Pont | Tertiary carbamyl triazoles |
| US3376306A (en) * | 1964-08-11 | 1968-04-02 | Du Pont | 1-carboxamido-3-amino-1, 2, 4-triazoles and a process for their preparation |
| EP0283876A2 (en) * | 1987-03-24 | 1988-09-28 | Bayer Ag | Substituted triazolinones |
| EP0332991A1 (en) * | 1988-03-18 | 1989-09-20 | Bayer Ag | Substituted triazoles |
| EP0398096A1 (en) * | 1989-05-18 | 1990-11-22 | Bayer Ag | Substituted triazolones |
| EP0425283A2 (en) * | 1989-10-25 | 1991-05-02 | Egis Gyogyszergyar | Novel triazolyl hydrazide derivatives and process for their preparation |
| US5194084A (en) * | 1989-05-18 | 1993-03-16 | Bayer Aktiengesellschaft | Herbicidal substituted triazolones |
| US5750718A (en) * | 1987-03-24 | 1998-05-12 | Bayer Aktiengesellschaft | Intermediates for herbicidal sulphonyl-aminocarbonlyltriazolinones having substituents which are bonded via sulphur |
-
1959
- 1959-03-11 BE BE576586A patent/BE576586A/en unknown
- 1959-03-17 GB GB921359A patent/GB919458A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3308131A (en) * | 1962-12-06 | 1967-03-07 | Du Pont | Tertiary carbamyl triazoles |
| US3376306A (en) * | 1964-08-11 | 1968-04-02 | Du Pont | 1-carboxamido-3-amino-1, 2, 4-triazoles and a process for their preparation |
| EP0283876A2 (en) * | 1987-03-24 | 1988-09-28 | Bayer Ag | Substituted triazolinones |
| EP0283876A3 (en) * | 1987-03-24 | 1989-07-26 | Bayer Ag | Substituted triazolinones |
| US5061311A (en) * | 1987-03-24 | 1991-10-29 | Bayer Aktiengesellschaft | Substituted triazolinone herbicides and plant growth regulators |
| US5750718A (en) * | 1987-03-24 | 1998-05-12 | Bayer Aktiengesellschaft | Intermediates for herbicidal sulphonyl-aminocarbonlyltriazolinones having substituents which are bonded via sulphur |
| EP0332991A1 (en) * | 1988-03-18 | 1989-09-20 | Bayer Ag | Substituted triazoles |
| US5021081A (en) * | 1988-03-18 | 1991-06-04 | Bayer Aktiengesellschaft | Herbicidal substituted triazoles |
| EP0398096A1 (en) * | 1989-05-18 | 1990-11-22 | Bayer Ag | Substituted triazolones |
| US5194084A (en) * | 1989-05-18 | 1993-03-16 | Bayer Aktiengesellschaft | Herbicidal substituted triazolones |
| EP0425283A2 (en) * | 1989-10-25 | 1991-05-02 | Egis Gyogyszergyar | Novel triazolyl hydrazide derivatives and process for their preparation |
| EP0425283A3 (en) * | 1989-10-25 | 1991-10-23 | Egis Gyogyszergyar | Novel triazolyl hydrazide derivatives and process for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| BE576586A (en) | 1959-07-01 |
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