ES329012A1 - Benzimidazoles and compositions thereof - Google Patents
Benzimidazoles and compositions thereofInfo
- Publication number
- ES329012A1 ES329012A1 ES329012A ES329012A ES329012A1 ES 329012 A1 ES329012 A1 ES 329012A1 ES 329012 A ES329012 A ES 329012A ES 329012 A ES329012 A ES 329012A ES 329012 A1 ES329012 A1 ES 329012A1
- Authority
- ES
- Spain
- Prior art keywords
- substituted
- fatty
- wetting agents
- alkyl
- amide
- 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
- 150000001556 benzimidazoles Chemical class 0.000 title abstract 4
- 239000000203 mixture Substances 0.000 title abstract 4
- -1 cyano, thiocyano, isothiocyano Chemical group 0.000 abstract 7
- 239000000080 wetting agent Substances 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 abstract 2
- 241000607479 Yersinia pestis Species 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 230000000855 fungicidal effect Effects 0.000 abstract 2
- 239000000417 fungicide Substances 0.000 abstract 2
- 230000002363 herbicidal effect Effects 0.000 abstract 2
- 239000004009 herbicide Substances 0.000 abstract 2
- 239000003701 inert diluent Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 abstract 1
- 229920005682 EO-PO block copolymer Polymers 0.000 abstract 1
- 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 1
- 239000005574 MCPA Substances 0.000 abstract 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 abstract 1
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000004996 alkyl benzenes Chemical class 0.000 abstract 1
- 150000001356 alkyl thiols Chemical class 0.000 abstract 1
- 150000001449 anionic compounds Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000005667 attractant Substances 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 150000002191 fatty alcohols Chemical class 0.000 abstract 1
- 150000002194 fatty esters Chemical class 0.000 abstract 1
- 239000003337 fertilizer Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000010445 mica Substances 0.000 abstract 1
- 229910052618 mica group Inorganic materials 0.000 abstract 1
- 239000003750 molluscacide Substances 0.000 abstract 1
- 230000002013 molluscicidal effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 125000002577 pseudohalo group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000011343 solid material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 235000000346 sugar Nutrition 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 150000008163 sugars Chemical class 0.000 abstract 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
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
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A biocidally active composition which contains as an active ingredient a substituted benzimidazole of the following formula:- wherein R1 , R2 , R3 and R* are the same or different and are H, alkyl, hydroxy, alkoxy, nitro, halogen, pseudo-halogen by which is meant cyano, thiocyano, isothiocyano or azido, substituted alkyl, carboxy, carboxy ester, carboxy amide, N-substituted carboxy amide, N- substituted amide, disubstituted amino, thiol, alkyl thiol and oxygenated derivatives thereof, sulphonic acid, esters amides and substituted amides thereof, and a heterocyclic ring attached to the [benzimidazole system through a nitrogen atom where X is trifluoromethyl or pentafluoromathyl where Y and Z are the same or different and are oxygen or sulphur where n is zero or one and where R5 is H, alkyl, aryl, alkenyl, aralkyl, cycloaliphatic or heterocyclic, substituted or unsubstituted, or when n is zero amino, monosubstituted amino or disubstituted amino, provided that where Y and Z are both oxygen then R5 is alkenyl, aralkyl, cycloaliphatic or heterocyclic, substituted or unsubstituted is used as a pesticide, a herbicide or a fungicide. The composition may also contain another herbicide (e.g. MCPA), insecticide, fungicide (e.g. copper derivative) or molluscicide. The composition may also contain one or more carriers, wetting agents, inert diluents, solid diluents, solvents, edible substances attractive to pests, pest attractants, paints and varnishes. The substituted benzimidazoles may be dissolved in a water immiscible solvent, such as a high boiling hydrocarbon, suitably containing dissolved emulsifying agents so as to act as a self-emulsifiable oil on addition to water. Inert diluents with which the substituted benzimidazoles and salts thereof may be incorporated include solid inert media comprising powdered or divided solid materials, for example, clays, sands, talc, mica and fertilizers, such products either comprising dust or larger particle size materials. The wetting agents used may comprise anionic compounds such as soaps, fatty sulphate esters such as dodecyl sodium sulphate, fatty aromatic sulphonates such as alkylbenzene isulphonates or butyl naphthalene sulphonate, more complex fatty sulphonates such as the amide condensation product of oleic acid and N-methyl taurine or the sodium sulphonate of dioctyl succinate. The wetting agents may also comprise non- ionic wetting agents such as condensation products of fatty acids, fatty alcohols or fatty substituted phenols with ethylene oxide, or fatty esters of sugars or polyhydric alcohols, or the products obtained from the latter by condensation with ethylene oxide, or the products known as block copolymers of ethylene oxide and propylene oxide. The wetting agents may also comprise cationic agents such as cetyl trimethylammonium bromide.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2958365 | 1965-07-13 | ||
| GB3241465A GB1151424A (en) | 1965-07-13 | 1965-07-13 | Benzimidazoles and compositions thereof |
| GB3241365 | 1965-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES329012A1 true ES329012A1 (en) | 1968-03-01 |
Family
ID=27258827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES329012A Expired ES329012A1 (en) | 1965-07-13 | 1966-07-12 | Benzimidazoles and compositions thereof |
Country Status (12)
| Country | Link |
|---|---|
| AT (3) | AT272759B (en) |
| BE (1) | BE683810A (en) |
| BR (1) | BR6680829D0 (en) |
| CH (1) | CH459654A (en) |
| DE (1) | DE1670717A1 (en) |
| ES (1) | ES329012A1 (en) |
| FR (1) | FR1503580A (en) |
| GB (1) | GB1151424A (en) |
| IL (1) | IL26042A (en) |
| LU (1) | LU51494A1 (en) |
| NL (1) | NL6609819A (en) |
| NO (1) | NO117670B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3625954A (en) * | 1968-03-20 | 1971-12-07 | Pfizer | 1-aroylbenzimidazoles |
| HU164653B (en) * | 1971-07-23 | 1974-03-28 | ||
| CN115477615B (en) * | 2022-10-17 | 2024-06-18 | 黄山学院 | N-(3-(benzimidazol-2-yl)phenyl)amide compounds and preparation methods and applications thereof |
-
1965
- 1965-07-13 GB GB3241465A patent/GB1151424A/en not_active Expired
-
1966
- 1966-06-27 IL IL2604266A patent/IL26042A/en unknown
- 1966-06-30 BR BR18082966A patent/BR6680829D0/en unknown
- 1966-07-06 LU LU51494A patent/LU51494A1/xx unknown
- 1966-07-07 BE BE683810D patent/BE683810A/xx unknown
- 1966-07-08 CH CH992066A patent/CH459654A/en unknown
- 1966-07-11 AT AT804167A patent/AT272759B/en active
- 1966-07-11 NO NO16388266A patent/NO117670B/no unknown
- 1966-07-11 AT AT804067A patent/AT275234B/en active
- 1966-07-11 AT AT663066A patent/AT267519B/en active
- 1966-07-11 DE DE19661670717 patent/DE1670717A1/en active Pending
- 1966-07-12 ES ES329012A patent/ES329012A1/en not_active Expired
- 1966-07-13 FR FR69329A patent/FR1503580A/en not_active Expired
- 1966-07-13 NL NL6609819A patent/NL6609819A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6680829D0 (en) | 1973-12-26 |
| AT275234B (en) | 1969-10-10 |
| NL6609819A (en) | 1967-01-16 |
| AT272759B (en) | 1969-07-25 |
| GB1151424A (en) | 1969-05-07 |
| DE1670717A1 (en) | 1970-12-03 |
| CH459654A (en) | 1968-07-15 |
| FR1503580A (en) | 1967-12-01 |
| LU51494A1 (en) | 1967-01-06 |
| BE683810A (en) | 1967-01-09 |
| IL26042A (en) | 1970-12-24 |
| AT267519B (en) | 1969-01-10 |
| NO117670B (en) | 1969-09-08 |
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