GB978855A - 1,1-(alkylene)bis(5-arylbiguanides), acid-addition salts thereof, and disinfecting oranitizing compositions containing same - Google Patents
1,1-(alkylene)bis(5-arylbiguanides), acid-addition salts thereof, and disinfecting oranitizing compositions containing sameInfo
- Publication number
- GB978855A GB978855A GB1312961A GB1312961A GB978855A GB 978855 A GB978855 A GB 978855A GB 1312961 A GB1312961 A GB 1312961A GB 1312961 A GB1312961 A GB 1312961A GB 978855 A GB978855 A GB 978855A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- nitro
- formula
- hydrogen
- 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
- 150000003839 salts Chemical class 0.000 title abstract 9
- 230000000249 desinfective effect Effects 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 7
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 aminophenyl Chemical group 0.000 abstract 5
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 3
- 230000002378 acidificating effect Effects 0.000 abstract 3
- 125000006307 alkoxy benzyl group Chemical group 0.000 abstract 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 3
- 125000006177 alkyl benzyl group Chemical group 0.000 abstract 3
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 3
- 125000005059 halophenyl group Chemical group 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000004982 aromatic amines Chemical class 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- VWCIQRLZBQDOLI-UHFFFAOYSA-N 3-chloro-4-propylsulfanylaniline hydrochloride Chemical compound Cl.CCCSC1=C(Cl)C=C(N)C=C1 VWCIQRLZBQDOLI-UHFFFAOYSA-N 0.000 abstract 1
- IVVYNVSBWVJZRX-UHFFFAOYSA-N 3-chloro-4-propylsulfinylaniline Chemical compound CCCS(=O)C1=CC=C(N)C=C1Cl IVVYNVSBWVJZRX-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000005263 alkylenediamine group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 230000003385 bacteriostatic effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 230000001408 fungistatic effect Effects 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 238000011012 sanitization Methods 0.000 abstract 1
- 239000008149 soap solution Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- C07C317/42—Y being a hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0978855/C1/1> (wherein CnH2n represents a bivalent alkylene bridge in which the free valence bonds are on two different carbon atoms and n is an integer from 2 to 12, and Q and Q1 each represent substituted phenyl having the formula <FORM:0978855/C1/2> wherein Y is hydrogen, halogen, trifluoromethyl, nitro, C1- 6 alkyl-O-, C1- 6 alkyl-S-, C1- 6 alkyl-SO- or C1- 6 alkyl-SO2-, Z is hydrogen, halogen, nitro, C1- 6 alkyl or C1- 6 alkyl-O-, R is alkyl, halo-C1- 6 alkyl, C2- 6 alkenyl, benzyl, ar-halobenzyl, ar-nitrobenzyl, ar-C1- 6 alkylbenzyl, ar-C1- 6 alkoxybenzyl, cyclohexyl, phenyl, C1- 6 alkylphenyl, nitrophenyl, C1- 6 alkoxyphenyl, halophenyl or, when neither Y nor Z is nitro, ar-aminobenzyl or aminophenyl, and X is -S-, -SO- or -SO2-) and acid addition salts thereof (including those with acidic resins-see Division C3), and their preparation by (a) reacting a 1,11(alkylene) bis (3-cyanoguanidine) of the formula <FORM:0978855/C1/3> with approximately two molecular proportions of an arylamine, preferably as an acid addition salt, of the formula <FORM:0978855/C1/4> (wherein R1 represents any of the values of R except ar-aminobenzyl or aminophenyl), or (b) reacting an alkylenediamine, as an acid addition salt, of the formula <FORM:0978855/C1/5> with approximately two molecular proportions of a 1-aryl-3-cyanoguanidine of the formula <FORM:0978855/C1/6> optionally followed in either case by (a) reduction of a compound wherein R1 is ar-nitrobenzyl or nitrophenyl and neither Y nor Z is nitro to the corresponding ar-aminobenzyl or aminophenyl compound, (b) oxidation of a compound wherein X is -S- or -SO- to the corresponding compound wherein X is -SO- or -SO2-, respectively, and/or (c) salt formation or conversion of a salt to the free base. The 1-aryl-3-cyanoguanidine starting materials are prepared by reacting approximately equimolecular amounts of a corresponding arylamine acid addition salt and an alkali metal dicyanamide. 4-n-Propylsulphinyl-3-chloroaniline is prepared by oxidizing 4-n-propylmercapto-3-chloroaniline hydrochloride with hydrogen peroxide in aqueous acetic acid, and is converted to the hydrochloride. The compounds of the invention have bactericidal, bacteriostatic, fungicidal and fungistatic activity, some of them have antiviral activity and others have amebacidal activity (see Division A5). Reference is made to the treatment with them of various disorders in animals.ALSO:The invention comprises addition salts of compounds of the general formula <FORM:0978855/C3/1> (wherein CnH2n represents a bivalent alkylene bridge in which the free valence bonds are on two different carbon atoms and n is an integer from 2 to 12, and Q and Q1 each represent substituted phenyl having the formula <FORM:0978855/C3/2> wherein Y is hydrogen, halogen, trifluoromethyl, nitro, C1-6 alkyl -O-, C1-6 alkyl-S-, C1-6 alkyl-SO- or C1-6 alkyl-SO2, Z is hydrogen, halogen, nitro, C1-6 alkyl or C1-6 alkyl-O-, R is alkyl, halo-C1-6 alkyl, C2-6 alkenyl, benzyl, ar-halobenzyl, ar-nitrobenzyl, ar-C1-6 alkylbenzyl, ar-C1-6 alkoxybenzyl, cyclohexyl, phenyl, C1-6 alkylphenyl, nitrophenyl, C1-6 alkoxyphenyl, halophenyl or, when neither Y nor Z is nitro, ar-aminobenzyl or aminophenyl, and X is -S-, -SO- or -SO2-) with acidic resins, e.g. sulphonated polystyrene.ALSO:The invention comprises disinfecting and sanitizing compositions containing a compound of the general formula <FORM:0978855/A5-A6/1> (wherein CnH2n represents a bivalent alkylene bridge in which the free valence bonds are on two different carbon atoms and n is an integer from 2 to 12, and Q and Q1 each represent substituted phenyl having the formula <FORM:0978855/A5-A6/2> wherein Y is hydrogen, halogen, trifluoromethyl, nitro, C1-6 alkyl-O-, C1-6 alkyl-S-, C1-6 alkyl-SO- or C1-6 alkyl-SO2-, Z is hydrogen, halogen, nitro, C1-6 alkyl or C1-6 alkyl-O-, R is alkyl, halo-C1-6 alkyl, C2-6 alkenyl, benzyl, ar-halobenzyl, ar-nitrobenzyl, ar-C1-6 alkylbenzyl, ar-C1-6 alkoxybenzyl, cyclohexyl, phenyl, C1-6 alkylphenyl, nitrophenyl, C1-6 alkoxyphenyl, halophenyl or, when neither Y or Z is nitro, ar-aminobenzyl or aminophenyl, and X is -S-, -SO- or -SO2-), or an acid addition salt thereof (including those with acidic resins), many are specified, and a carrier. The active ingredients may be used in soap solution or sulfonate detergent solution to treat cotton cloth.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2269260A | 1960-04-18 | 1960-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB978855A true GB978855A (en) | 1964-12-23 |
Family
ID=21810934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1312961A Expired GB978855A (en) | 1960-04-18 | 1961-04-12 | 1,1-(alkylene)bis(5-arylbiguanides), acid-addition salts thereof, and disinfecting oranitizing compositions containing same |
Country Status (3)
| Country | Link |
|---|---|
| CH (3) | CH437649A (en) |
| FR (2) | FR1309831A (en) |
| GB (1) | GB978855A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4359555A (en) | 1979-06-29 | 1982-11-16 | Ciba-Geigy Corporation | Salts formed from formamidines with polymers containing sulfonic acid groups |
| GB2349644A (en) * | 1999-05-01 | 2000-11-08 | Biointeractions Ltd | Infection resistant polymers, methods for their preparation, and their uses |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0113070B1 (en) * | 1982-12-20 | 1988-01-13 | American Cyanamid Company | The use of substituted nitro and cyanoguanidines for increasing crop yield |
-
1961
- 1961-04-12 GB GB1312961A patent/GB978855A/en not_active Expired
- 1961-04-17 FR FR858983A patent/FR1309831A/en not_active Expired
- 1961-04-18 CH CH1654765A patent/CH437649A/en unknown
- 1961-04-18 CH CH455761A patent/CH407980A/en unknown
- 1961-04-18 CH CH8116661A patent/CH421939A/en unknown
- 1961-07-13 FR FR868001A patent/FR1582M/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4359555A (en) | 1979-06-29 | 1982-11-16 | Ciba-Geigy Corporation | Salts formed from formamidines with polymers containing sulfonic acid groups |
| GB2349644A (en) * | 1999-05-01 | 2000-11-08 | Biointeractions Ltd | Infection resistant polymers, methods for their preparation, and their uses |
| US7771743B1 (en) | 1999-05-01 | 2010-08-10 | Biointeractions, Ltd. | Infection resistant polymers, their preparation and uses |
Also Published As
| Publication number | Publication date |
|---|---|
| CH437649A (en) | 1967-06-15 |
| FR1309831A (en) | 1962-11-23 |
| FR1582M (en) | 1962-11-26 |
| CH421939A (en) | 1966-10-15 |
| CH407980A (en) | 1966-02-28 |
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