GB972008A - Halogenated methylthiohydantoins - Google Patents
Halogenated methylthiohydantoinsInfo
- Publication number
- GB972008A GB972008A GB1716863A GB1716863A GB972008A GB 972008 A GB972008 A GB 972008A GB 1716863 A GB1716863 A GB 1716863A GB 1716863 A GB1716863 A GB 1716863A GB 972008 A GB972008 A GB 972008A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- substituted
- alkyl
- formula
- unsubstituted
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds of formula <FORM:0972008/C1/1> where R1 is H, or an alkyl, carboxylic acyl or nitro radical, and R2 and R3 are H, or substituted or unsubstituted alkyl, cycloalkyl, aralkyl, aryl, or heterocyclic radicals, or R2 and R3 together form a substituted or unsubstituted polymethylene bridge. Indicated substituents of R2 and R3 are alkyl, alkoxy, or alkoxycarbonyl radicals or halogen atoms. The compounds are made by reacting hydantoins of formula <FORM:0972008/C1/2> where R1, R2 and R3 have the same meaning as above, with fluorodichloromethane sulphenic acid chloride, preferably in an aqueous medium or an inert organic solvent such as benzene, dioxan, or chloroform, in the presence of an acid-binding agent. The compounds may also be prepared by reacting the corresponding 3-trichloromethylthiohydantoins with commercial anhydrous hydrofluoric acid. This reaction is generally carried out at atmospheric pressure at 0-20 DEG C. with excess hydrogen fluoride present as solvent. Organic solvents, e.g. nitrobenzene, diethylether, dioxan, and tetrahydrofuran may also be used. Examples are given in which R2 and R3 are H1 -CH3, and carboethoxy groups, and in which R2 is H, and R3 is a phenyl or hexyl group, and where R2 is carboethoxy and R3 is a methyl group. Examples also show compounds in which R2 and R3 together form a polymethylene bridge, e.g. where R2 and R3 together are hexyl or pentyl, the hexyl radical is also shown substituted by methyl groups. The compounds are useful as pesticides, especially fungicides (see Division A5).ALSO:New pesticidal, especially fungicidal, compositions, containing compounds of formula <FORM:0972008/A5-A6/1> where R1 is H, or an alkyl, carboxylic acyl, or nitro group, and R2 and R3 are H, or substituted or unsubstituted alkyl, cycloalkyl, aralkyl, aryl or heterocyclic residues, or together form a substituted or unsubstituted polymethylene bridge. The compounds are used in suitable solid or liquid extenders or diluents, as dusts, or aqueous suspensions, solutions or emulsions. Combination with other fungicides and/or insecticides is possible. The compositions may contain adhesives and non-ionic emulsifiers.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF36695A DE1168914B (en) | 1962-05-02 | 1962-05-02 | Process for the preparation of hydantoin derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB972008A true GB972008A (en) | 1964-10-07 |
Family
ID=7096565
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1716863A Expired GB972008A (en) | 1962-05-02 | 1963-05-01 | Halogenated methylthiohydantoins |
Country Status (7)
Country | Link |
---|---|
AT (1) | AT239801B (en) |
BE (1) | BE631731A (en) |
CH (1) | CH428308A (en) |
DE (1) | DE1168914B (en) |
DK (1) | DK107909C (en) |
GB (1) | GB972008A (en) |
NL (1) | NL292187A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3960883A (en) * | 1973-09-03 | 1976-06-01 | Ciba-Geigy Corporation | Imidazolidine-2,4-dione derivatives and their use as pesticides |
US4198423A (en) * | 1979-03-20 | 1980-04-15 | Basf Aktiengesellschaft | 1,3-Bis-(trihalomethylsulfenyl)-imidazoline-2,4-diones |
US4607044A (en) * | 1970-05-15 | 1986-08-19 | Duphar International Research B.V. | Insecticidal use of ureas and thioureas |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3222523A1 (en) * | 1982-06-16 | 1983-12-22 | Bayer Ag, 5090 Leverkusen | N-SULFENYLATED HYDANTOINE |
DE3305203A1 (en) * | 1983-02-16 | 1984-08-16 | Bayer Ag, 5090 Leverkusen | N-SULFENYLATED HYDANTOINE, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A MICROBICIDE |
AU578068B2 (en) * | 1984-03-08 | 1988-10-13 | Nippon Zoki Pharmaceutical Co., Ltd. | Hydantoin derivatives and pharmaceutical compositions containing them |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE921290C (en) * | 1948-05-18 | 1954-12-13 | Standard Oil Dev Co | Procedure for combating pests |
US2920997A (en) * | 1955-02-14 | 1960-01-12 | Pittsburgh Coke And Chemical C | Fungicidal composition of a hydantoin selected from the group consisting of 5, 5 polymethylene and 5, 5 diaryl, and 5, 5 aryl, alky hydantion |
-
0
- NL NL292187D patent/NL292187A/xx unknown
-
1962
- 1962-05-02 DE DEF36695A patent/DE1168914B/en active Pending
-
1963
- 1963-04-19 CH CH495163A patent/CH428308A/en unknown
- 1963-04-30 BE BE631731A patent/BE631731A/en unknown
- 1963-05-01 DK DK205963A patent/DK107909C/en active
- 1963-05-01 GB GB1716863A patent/GB972008A/en not_active Expired
- 1963-05-02 AT AT355363A patent/AT239801B/en active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4607044A (en) * | 1970-05-15 | 1986-08-19 | Duphar International Research B.V. | Insecticidal use of ureas and thioureas |
US3960883A (en) * | 1973-09-03 | 1976-06-01 | Ciba-Geigy Corporation | Imidazolidine-2,4-dione derivatives and their use as pesticides |
US4198423A (en) * | 1979-03-20 | 1980-04-15 | Basf Aktiengesellschaft | 1,3-Bis-(trihalomethylsulfenyl)-imidazoline-2,4-diones |
Also Published As
Publication number | Publication date |
---|---|
NL292187A (en) | |
AT239801B (en) | 1965-04-26 |
DK107909C (en) | 1967-07-17 |
BE631731A (en) | 1963-11-18 |
DE1168914B (en) | 1964-04-30 |
CH428308A (en) | 1967-01-15 |
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