GB716553A - Improvements in or relating to n-thiotrichloromethyl compounds - Google Patents
Improvements in or relating to n-thiotrichloromethyl compoundsInfo
- Publication number
- GB716553A GB716553A GB1454651A GB1454651A GB716553A GB 716553 A GB716553 A GB 716553A GB 1454651 A GB1454651 A GB 1454651A GB 1454651 A GB1454651 A GB 1454651A GB 716553 A GB716553 A GB 716553A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trichloromethylthio
- dione
- compounds
- methyl
- oxazolidine
- 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
-
- 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
- A01N47/02—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 no bond to a nitrogen atom
- A01N47/04—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 no bond to a nitrogen atom containing >N—S—C≡(Hal)3 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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises the following compounds: <FORM:0716553/IV (b)/1> where X is -CO- or -SO2- and R1 and R2 are organic residues (which may be joined) attached via carbon atoms; <FORM:0716553/IV (b)/2> where X is -CO- and Y is -SO2-, R being an organic residue attached via carbon atoms; <FORM:0716553/IV (b)/3> where R completes a 5-membered ring containing an additional hetero atom; and <FORM:0716553/IV (b)/4> where X and Y are terminal carbon atoms of the same 5-membered chain which may include an oxygen, nitrogen or sulphur atom. The invention also includes the preparation of the above by reacting perchloromethyl mercaptan with the appropriate nitrogen compound or alkali metal salt thereof, preferably in a liquid medium such as aqueous alkali. The invention further includes an improved process of making the above compounds and those of the parent Specification by carrying out the reaction in an aqueous medium containing a neutral water-soluble salt, preferably a salt of the same metal that has been used to form the salt of the nitrogen compound; sodium or potassium chloride is suitable. Preferred compounds are type (1), where R1 is aromatic and R2 is a hydrocarbon or halogenated hydrocarbon group; (2) where R1 is aromatic; (3) where the 5-membered ring is that of a hydantoin, oxazolidinedione or thiazolidinedione; and (4) of the formula <FORM:0716553/IV (b)/5> where X is O, S or -CHY- and the Y symbols represent hydrogen, halogen or alkyl. Full details are given of the procedures for making the compounds. Examples show the preparation of the following: 3-trichloromethylthio-5-methyl - 5 - ethyl - oxazolidine - 2 : 4 - dione, N - trichloromethylthio - N - phenyl - benzenesulphonamide, 1 - nitro - 3 - trichloromethylthio - 5 : 5 - dimethylhydantoin, 3 - trichloromethylthio - thiazolidine - 2 : 4 - dione, N - trichloromethylthio - saccharin, N - trichloromethylthiomorpholine, N-trichloromethylthio-acetanilide and N - trichloromethylthio - diacetamide. Other products mentioned are the N-trichloromethylthio derivatives of 5 : 5-dimethyl-oxazolidine-2 : 4-dione, 5 : 5-pentamethylene-oxazolidine - 2 : 4 - dione, 5 - phenyl - 5 - methyl - oxazolidine - 2 : 4 - dione, 5 - isobutyl - 5 - methyl - oxazolidine - 2 : 4 - dione, 5 - cyclopropyl - 5 - methyl - oxazolidine - 2 : 4 - dione, N - butyl - benzenesulphonamide, 5 : 5 - dimethylhydantoin and 1-acetyl-5 : 5-dimethylhydantoin.ALSO:Fungicidal, insecticidal, parasiticidal and germicidal compositions comprise one of the following types of compounds together with a diluent in intimate admixture therewith:- (1) <FORM:0716553/VI/1> where X is -CO- or -SO2- and R1 and R2 are organic radicals (which may be joined) attached via carbon atoms; (2) <FORM:0716553/VI/2> where X is -CO- and Y is -SO2-, R being an organic residue attached via carbon atoms; (3) <FORM:0716553/VI/3> where R completes a 5-membered ring containing an additional hetero atom; and (4) <FORM:0716553/VI/4> where X and Y are terminal carbon atoms of the same 5-membered chain which may include an oxygen, nitrogen or sulphur atom. The compounds may be applied in various ways, e.g. (1) powdered and applied as undiluted dust or mixed with a solid carrier such as clay, talc or bentonite; (2) as a solution in acetone, ethanol, benzene, naphtha or other solvent or (3) dispersed in water, preferably with an anionic or non-ionic wetting agent. They may be mixed with hormones, herbicides, fertilizers or other parasiticides such as arsenates, fluorides, rotenone, DDT or benzene hexachloride. Figures are given of the results obtained with the following compounds:- 3-trichloromethylthio-5 : 5-dimethyl-oxazolidine-2 : 4-dione and the corresponding 5-methyl-5-ethyl, 5-methyl-5-isobutyl, 5-methyl-5-cyclopropyl, 5-methyl-5-phenyl and 5 : 5- pentamethylene compounds, N - trichloromethylthio - morpholine, 3-trichloromethylthio-thiazolidine - 2 : 4 - dione, N-trichloromethylthiosaccharin, N-trichloromethylthio-N-butylbenzene-sulphonamide, N-trichloromethylthio-N-phenyl-benzenesulphonamide, 3-trichloromethylthio-5 : 5-dimethylhydantoin and its 1-nitro and 1-acetyl derivatives. Other suitable compounds are mentioned.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1454651A GB716553A (en) | 1951-06-19 | 1951-06-19 | Improvements in or relating to n-thiotrichloromethyl compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1454651A GB716553A (en) | 1951-06-19 | 1951-06-19 | Improvements in or relating to n-thiotrichloromethyl compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB716553A true GB716553A (en) | 1954-10-06 |
Family
ID=10043174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1454651A Expired GB716553A (en) | 1951-06-19 | 1951-06-19 | Improvements in or relating to n-thiotrichloromethyl compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB716553A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0217108A2 (en) * | 1985-09-03 | 1987-04-08 | Bayer Ag | Material preservative |
CN115784946A (en) * | 2022-11-10 | 2023-03-14 | 河北冠龙农化有限公司 | Synthesis method of N-phenyl-N-trichloromethylthio benzenesulfonamide |
-
1951
- 1951-06-19 GB GB1454651A patent/GB716553A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0217108A2 (en) * | 1985-09-03 | 1987-04-08 | Bayer Ag | Material preservative |
EP0217108A3 (en) * | 1985-09-03 | 1987-04-22 | Bayer Ag | Material preservative |
US4764433A (en) * | 1985-09-03 | 1988-08-16 | Bayer Aktiengesellschaft | Agent for the protection of materials |
CN115784946A (en) * | 2022-11-10 | 2023-03-14 | 河北冠龙农化有限公司 | Synthesis method of N-phenyl-N-trichloromethylthio benzenesulfonamide |
CN115784946B (en) * | 2022-11-10 | 2024-03-29 | 河北冠龙农化有限公司 | Synthesis method of N-phenyl-N-trichloromethylthiobenzene sulfonamide |
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