GB946397A - Production of halogenated n, n-disubstituted carbamyl halides - Google Patents
Production of halogenated n, n-disubstituted carbamyl halidesInfo
- Publication number
- GB946397A GB946397A GB2641962A GB2641962A GB946397A GB 946397 A GB946397 A GB 946397A GB 2641962 A GB2641962 A GB 2641962A GB 2641962 A GB2641962 A GB 2641962A GB 946397 A GB946397 A GB 946397A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- chlorine
- give
- carbamyl
- halogen
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/04—Carbamic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/02—Carbamic acids; Salts of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Halogenated N, N-disubstituted carbamyl halides are obtained by reacting a compound R1R2N.COX, where R1 and R2 are aliphatic, cycloaliphatic or araliphatic radicals, or together represent members of a heterocyclic ring, and X is halogen, with a halogenating agent. "Halogen" means F, Cl or Br. Suitable halogenating agents are fluorine, chlorine bromine and sulphuryl halides. In preferred starting materials, R1 is C1-12 aliphatic hydrocarbon, C5-12 cycloaliphatic hydrocarbon, or C7-12 araliphatic hydrocarbon; R2 is as R1, but may also be C2-8 aliphatic hydrocarbon substituted by -NR3.COX, in which R3 is C1-4 alkyl and X is halogen (at least 2 carbon atoms being between the 2 nitrogen atoms); or R1 and R2 together are members of a 5-7-membered heterocyclic ring including the N atom, which ring is hydrocarbon or may contain one further O, N or S atom in the ring; or R1 and R2 together are members of a heterocyclic 6-membered ring containing the N atom and a further >NCOX group. In the above definitions R1 and R2 may be substituted by 1 or 2 halogen atoms, ether oxygen, thioether sulphur, carboxyl, carboxylic ester or nitrile groups. From one to all aliphatic hydrogen atoms may be replaced by halogen in the reaction. Novel compounds. The following types of compound are claimed as novel: R4R5NCOCl, XCH2N(R6)COX, (XCH2)2NCOX, CH3CHX. N(R6)COX and (CH3CHX)2NCOX, in which X is halogen; R4 is C1-4 alkyl; R5 is as R4, or is C2-8 alkyl substituted by -NR3.COX (in which R3 is C1-4 alkyl), there being at least 2 carbon atoms between the 2 nitrogen atoms; or R4 and R5 together represent members of a heterocyclic 5-7-membered ring including the nitrogen atom and possibly one further N, O or S atom, otherwise of hydrocarbon structure; or a heterocyclic 6-membered ring including the nitrogen atom and a further >NCOX group, otherwise of hydrocarbon structure; the radicals R4 and R5 containing at least one halogen atom in addition to X; and R6 is C1-4 alkyl. These novel compounds are fungicides. In examples (1) dimethylcarbamyl chloride and chlorine give methyl-chloromethyl-, bis(chloromethyl)-, dichloromethyl-chloromethyl carbamyl chlorides and a higher chlorinated product; (2) dimethylcarbamyl chloride and SOCl2 give methyl-chloromethylcarbamyl chloride; (3) bis(BETA-chloroethyl) carbamyl chloride and chlorine give bis(pentachloroethyl) carbamyl chloride; (4) diethylcarbamyl chloride and chlorine give the same product as in (3); (5) piperidyl carbamyl chloride and chlorine give chlorinated products up to pentachloropiperidylcarbamyl chloride; (6) dimethylcarbamyl chloride and chlorine give methyl-chloromethyl- and bis(chloromethyl) carbamyl chloride; (7) morpholylcarbamyl chloride and chlorine give chlorinated products up to tetrachloromorpohyl carbamyl chloride; (8) pyrrolidylcarbamyl chloride and chlorine give chlorinated products up to tetrachloropyrrolidylcarbamyl chloride; (9) N-isopropyl-N-benzyl carbamyl chloride and chlorine give a chlorinated product; (10) N-methyl-N-cyclohexylcarbamyl chloride and chlorine give a chlorinated product; (11) piperazine-dicarbamyl chloride and chlorine give a chlorinated product; (12) dimethylcarbamyl chloride and fluorine give a fluorinated product; and (13) diethylcarbamyl chloride and chlorine give N-ethyl-N-(a -chloroethyl) carbamyl chloride and N,N-bis(a -chloroethyl) carbamyl chloride. Other starting materials are listed.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB63208A DE1154087B (en) | 1961-07-11 | 1961-07-11 | Process for the preparation of halogenated carbamic acid halides |
Publications (1)
Publication Number | Publication Date |
---|---|
GB946397A true GB946397A (en) | 1964-01-15 |
Family
ID=6973889
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2641962A Expired GB946397A (en) | 1961-07-11 | 1962-07-10 | Production of halogenated n, n-disubstituted carbamyl halides |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH427775A (en) |
DE (1) | DE1154087B (en) |
GB (1) | GB946397A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2706683C2 (en) * | 1977-02-17 | 1985-02-21 | Basf Ag, 6700 Ludwigshafen | Process for the preparation of N-fluoromethylcarbamic acid fluorides |
DE2826012A1 (en) * | 1978-06-14 | 1980-01-03 | Basf Ag | NEW BIS- (N-HALOGENMETHYL) -CARBAMID ACID ESTERS AND METHOD FOR THE PRODUCTION THEREOF |
DE3013270A1 (en) * | 1980-04-05 | 1981-10-15 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING 1-MONOCHLORAETHYLCARBAMIDSAEURECHLORID |
-
1961
- 1961-07-11 DE DEB63208A patent/DE1154087B/en active Pending
-
1962
- 1962-07-05 CH CH807162A patent/CH427775A/en unknown
- 1962-07-10 GB GB2641962A patent/GB946397A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH427775A (en) | 1967-01-15 |
DE1154087B (en) | 1963-09-12 |
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