IL33136A - Isothiocyanatophenyl-n-methylcarbamate and processes for its preparation - Google Patents
Isothiocyanatophenyl-n-methylcarbamate and processes for its preparationInfo
- Publication number
- IL33136A IL33136A IL33136A IL3313669A IL33136A IL 33136 A IL33136 A IL 33136A IL 33136 A IL33136 A IL 33136A IL 3313669 A IL3313669 A IL 3313669A IL 33136 A IL33136 A IL 33136A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- formula
- compound
- reaction
- composition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title description 4
- GYHZOCHKCBFKHS-UHFFFAOYSA-N (2-isothiocyanatophenyl)-methylcarbamic acid Chemical compound CN(C1=CC=CC=C1N=C=S)C(=O)O GYHZOCHKCBFKHS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- -1 3-Isothiocyanatophenyl-N-methylcarbamate Chemical compound 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 230000000895 acaricidal effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- BWZDLMGVEVSNBI-UHFFFAOYSA-N 3-isothiocyanatophenol Chemical compound OC1=CC=CC(N=C=S)=C1 BWZDLMGVEVSNBI-UHFFFAOYSA-N 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 150000003512 tertiary amines Chemical class 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- A01N47/46—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 containing —N=C=S groups
Landscapes
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
and processes for its preparation 2 The present Invention relates to to a process its production to its use a3 It is that can be used as for example British Patent Specification 894 which has attained considerable importance in present invention provides of the formula The compound of the present invention exhibits strong acaricidal properties and has an acaricidal activity which is higher than that of the above mentioned known The present invention also provides a process for the production of the of the formula in which of the formula OH is reacted with methylisocyanate in the presence of a solvent term includes a mere or 3 atophenol of the formula in a first converted with an excess of phosgene into the chloroformic acid ester and this is reacted with The to be used as starting material can be prepared in a simple manner by suspending in water at room the appropriate known Concentrated hydrochloric acid is added to the and thiophosgene is added The then separating out need not be but can be used The reaction according to variant may be illustrated by the following formula The reaction is carried out in inert Suitable for this purpose for such as benzine alkylarylpolyglycol alkyl sulphonates and aryl and preferred examples of dispersing agents include sulphite liquors and active according to the invention may be present in the formulations in admixture with other active The formulations in to ferably from to per cent by weight active The active may be used as such or in the form of their formulations or of the application forms prepared such as pastes and Application may take place in the usual example by scattering or concentrations of active compound in the preparations may vary fairly wide In the concentrations are from to20 per cent by preferably from to 5 per cent by In the case of methods of very concentrated preparations are also for example with contents of active compound of from 10 to 80 per cent by the also show an activit against against fungi infest as well as against terrestrial The present invention also provides an acaricidal the containing as active ingredient according to the present invention in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing The present invention provides a method of reference to are Le A 11 9 10 insufficientOCRQuality
Claims (19)
1.*. 3-Isothiocyanatophenyl-N-methylcarbamate of the formula
2* A process for the production of 3-isothiocyanato-phenyl-N-methylcarhamate according to formula (1) in Claim 1 wherein (a) m-isothiocyanatophenol of the formula OH is reacted with methylisocyanate in the presence of a solvent, or (b) m-isothiocyanatophenol of the formula (2) is converted with an excess of phosgene into the chloroformic acid ester and this latter compound is reacted with methylamine.
3. A process according to Claim 2 (a) in which the reaction is carried out at 10° to 50°C.
4. A process according to Claim 2 (a) or 3 in which the reaction is effected in the presence of a tertiary amine as a catalyst.
5. A process according to Claim 4 in which the tertiary amine is triethylamine, dimeth lbenzylamine or dlazabicyclo-octane. - 11 - 33136/2
6. A process according to Claim 2 (b) in which the first step Is carried out at -10° to +10°C.
7. A process according to Claim 2 (b) or 6 in which the reaction of the chloroformic acid ester and me hylamine is carried out at -10° to +10°C.
8. A process according to any of Claims 2 (b), 6 and 7 in which the first reaction step is effected in the presence of an inert solvent,
9» A process according to any of Claims 2 (b) and 6 to 8 in which the reaction of the chloroformic acid ester and methylamine is effected in the presence of an inert solvent,
10. A process according to any of Claims 2 (b) and 6 to 9 in which during the first step the pH is kept below 7 by the dropwise addition of a base.
11. A process according to Claim 10 in which the base is sodium hydroxide.
12. A process for the production of 3-isothiocyanatophenyl-H-methylcarbamate according to Claim 1 substantially as described in Example 1.
13. Acaricidal compositions containing as active ingredient a compound of formula (l) in Claim 1 in admixture with a solid diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
14. A composition according to Claim 13 containing from 0.1 to 95$ b weight of the active compound.
15. A composition according to Claim 14 containing from - 12 - 33136/2
16. A method of combating acarids which comprises applying to the acarids or an acarid habitat a compound of formula (l) in Claim 1 alone or in the form of a composition according to Claims 13 to 15.
17. Α· method according to Claim 16 in which a composition is used containing from 0.005 to 5 ° and preferably from 0.001 to 3°/° of the active compound, by weight.
18. A method according to Claim 16 in which a composition is used containing from 10 to 80$ of the active compound, by weight.
19* Crops protected from damage by acarids by being grown in areas in which immediately prior to and/or during the time of growing a compound of formula (1) in Claim 1 was applied alone or in admixture with a solid or liquid diluent or carrier. PC/rb
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681808043 DE1808043A1 (en) | 1968-11-09 | 1968-11-09 | Isothiocyanato-phenyl-N-methylcarbamates and processes for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33136A0 IL33136A0 (en) | 1969-12-31 |
| IL33136A true IL33136A (en) | 1972-08-30 |
Family
ID=5712894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33136A IL33136A (en) | 1968-11-09 | 1969-10-07 | Isothiocyanatophenyl-n-methylcarbamate and processes for its preparation |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE741448A (en) |
| CH (1) | CH524956A (en) |
| DE (1) | DE1808043A1 (en) |
| ES (1) | ES373357A1 (en) |
| FR (1) | FR2022972A1 (en) |
| GB (1) | GB1247748A (en) |
| IL (1) | IL33136A (en) |
| NL (1) | NL6916540A (en) |
-
1968
- 1968-11-09 DE DE19681808043 patent/DE1808043A1/en active Pending
-
1969
- 1969-10-07 CH CH1505469A patent/CH524956A/en not_active IP Right Cessation
- 1969-10-07 IL IL33136A patent/IL33136A/en unknown
- 1969-10-23 GB GB51933/69A patent/GB1247748A/en not_active Expired
- 1969-11-03 NL NL6916540A patent/NL6916540A/xx unknown
- 1969-11-07 FR FR6938542A patent/FR2022972A1/fr not_active Withdrawn
- 1969-11-07 BE BE741448D patent/BE741448A/xx unknown
- 1969-11-08 ES ES373357A patent/ES373357A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE741448A (en) | 1970-05-08 |
| DE1808043A1 (en) | 1970-05-27 |
| IL33136A0 (en) | 1969-12-31 |
| NL6916540A (en) | 1970-05-12 |
| ES373357A1 (en) | 1971-12-16 |
| FR2022972A1 (en) | 1970-08-07 |
| CH524956A (en) | 1972-07-15 |
| GB1247748A (en) | 1971-09-29 |
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