GB811861A - Improvements in or relating to thio-carbaminates, bisthio-carbaminates and bisdithio-carbaminates, methods of producing such substances and to compositions containing such substances for treating plants - Google Patents
Improvements in or relating to thio-carbaminates, bisthio-carbaminates and bisdithio-carbaminates, methods of producing such substances and to compositions containing such substances for treating plantsInfo
- Publication number
- GB811861A GB811861A GB9531/56A GB953156A GB811861A GB 811861 A GB811861 A GB 811861A GB 9531/56 A GB9531/56 A GB 9531/56A GB 953156 A GB953156 A GB 953156A GB 811861 A GB811861 A GB 811861A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- atoms
- atom
- bis
- ring
- 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
- 239000000203 mixture Substances 0.000 title abstract 3
- 239000000126 substance Substances 0.000 title 2
- 125000004429 atom Chemical group 0.000 abstract 12
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 9
- 125000002947 alkylene group Chemical group 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000000732 arylene group Chemical group 0.000 abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract 6
- 150000001768 cations Chemical class 0.000 abstract 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000012876 carrier material Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 230000000361 pesticidal effect Effects 0.000 abstract 2
- 230000008635 plant growth Effects 0.000 abstract 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 230000004936 stimulating effect Effects 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 abstract 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- -1 methyl ethyl Chemical group 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940023144 sodium glycolate Drugs 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/21—Radicals derived from sulfur analogues of carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises thiocarbaminates, bis-thiocarbaminates and bis-dithiocarbaminates of the formul : <FORM:0811861/IV (b)/1> and <FORM:0811861/IV (b)/2> in which R1 and R2 represent hydrogen and/or alkyl groups or form, together with the nitrogen atom, a ring of not more than 6 atoms, R3 represents a bivalent, if desired substituted, alkylene, aralkylene or arylene group, R5 represents a bivalent alkylene, aralkylene or arylene group or, together with the two nitrogen atoms and the two groups R2 forms a ring of not more than 6 atoms, or, together with one nitrogen atom and the group R2 attached to this atom, a ring of not more than 6 atoms, X represents an NH2 or substituted NH2 group, an OH group or an OH group in which the hydrogen atom is replaced by a cation, or an alkyl, aralkyl or aryl group, and Z represents an oxygen or sulphur atom. R1 and R2 are preferably C1-4 alkyl groups, particularly methyl ethyl or isopropyl groups; R3 and R5 are preferably phenylene or C1-4 alkylene groups, particularly methylene, ethylene, isopropylene, propylene or butylene groups; X is preferably an OH group or a C1-6 alkoxy group, particularly a methoxy or ethoxy group. Compounds of the first general formula and of the second general formula in which Z represents oxygen, are obtained by reacting a compound <FORM:0811861/IV (b)/3> where Me is a metal cation and Alk is an alkylene group, with a compound <FORM:0811861/IV (b)/4> or <FORM:0811861/IV (b)/5> respectively. Compounds of the second general formula in which Z represents sulphur are obtained by reacting a compound <FORM:0811861/IV (b)/6> wherein Me is a metal cation, with a compound <FORM:0811861/IV (b)/7> wherein Hlg is a halogen atom. The examples describe the preparation of di-sodium-S:S1-bis - (carboxymethyl) - ethylene bis - dithiocarbaminate and N:N - dimethylthiocarbamyl-glycolic acid. Reference is also made to products of the formul : <FORM:0811861/IV (b)/8> <FORM:0811861/IV (b)/9> <FORM:0811861/IV (b)/100> <FORM:0811861/IV (b)/111> to the corresponding free acids; to S:S1-bis-(carboxymethyl) - ethylene - bis - dithiocarbaminate; and to other salts and esters of such compounds. A starting material of the formula: <FORM:0811861/IV (b)/122> is prepared by adding chloroacetamide to the solution of the compound <FORM:0811861/IV (b)/133> obtained by reacting sodium glycolate with carbon disulphide and caustic potash.ALSO:Pesticidal and plant growth stimulating compositions comprise thiocarbaminates, bisthiocarbaminates and bis-dithio-carbaminates of the formulae <FORM:0811861/I/1> and <FORM:0811861/I/2> in which R1 and R2 represent hydrogen and/or alkyl groups or form, together with the nitrogen atom, a ring of not more than 6 atoms, R3 represents a bivalent, if desired substituted, alkylene, aralkylene or arylene group, R5 represents a bivalent alkylene, aralkylene or arylene group, or, together with the two nitrogen atoms and the two groups R2, forms a ring of not more than 6 atoms, or, together with one nitrogen atom and the group R2 attached to this atom, a ring of not more than 6 atoms, X represents an NH2 or substituted NH2 group, an OH group or an OH group in which the hydrogen atom is replaced by a cation (e.g. sodium) or an alkyl, aralkyl group, and Z represents an oxygen or sulphur atom, together with a liquid or solid inert carrier material, preferably water.ALSO:Pesticidal and plant growth stimulating compositions comprise thiocarbaminates, bis-thiocarbaminates and bis-dithio-carbaminates of the formul : <FORM:0811861/VI/1> and <FORM:0811861/VI/2> in which R1 and R2 represent hydrogen and/or alkyl groups or form, together with the nitrogen atom, a ring of not more than 6 atoms, R3 represents a bivalent, if desired substituted, alkylene, aralkylene or arylene group, R5 represents a bivalent alkylene, aralkylene or arylene group, or, together with the two nitrogen atoms and the two groups R2 forms a ring of not more than 6 atoms, or, together with one nitrogen atom and the group R2 attached to this atom, a ring of not more than 6 atoms, X represents an NH2 or substituted NH2 group, an OH group or an OH group in which the hydrogen atom is replaced by a cation (e.g. sodium) or an alkyl, aralkyl or aryl group, and Z represents an oxygen or sulphur atom, together with a liquid or solid inert carrier material, preferably water.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL811861X | 1955-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB811861A true GB811861A (en) | 1959-04-15 |
Family
ID=19838717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9531/56A Expired GB811861A (en) | 1955-03-30 | 1956-03-27 | Improvements in or relating to thio-carbaminates, bisthio-carbaminates and bisdithio-carbaminates, methods of producing such substances and to compositions containing such substances for treating plants |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB811861A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1176796B (en) * | 1960-06-24 | 1964-08-27 | Monsanto Canada Ltd | Bacteriostatic agent |
| DE1201008B (en) * | 1959-01-16 | 1965-09-16 | Monsanto Canada Ltd | Disinfectants |
| CN102093304A (en) * | 2011-02-26 | 2011-06-15 | 西陇化工股份有限公司 | Preparation method of 3-R-2-sulfo-4-oxazolidinone |
-
1956
- 1956-03-27 GB GB9531/56A patent/GB811861A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1201008B (en) * | 1959-01-16 | 1965-09-16 | Monsanto Canada Ltd | Disinfectants |
| DE1176796B (en) * | 1960-06-24 | 1964-08-27 | Monsanto Canada Ltd | Bacteriostatic agent |
| CN102093304A (en) * | 2011-02-26 | 2011-06-15 | 西陇化工股份有限公司 | Preparation method of 3-R-2-sulfo-4-oxazolidinone |
| CN102093304B (en) * | 2011-02-26 | 2013-05-22 | 西陇化工股份有限公司 | Preparation method of 3-R-2-sulfo-4-oxazolidinone |
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