GB1193461A - Substituted 2-Aminobenzimidazoles - Google Patents
Substituted 2-AminobenzimidazolesInfo
- Publication number
- GB1193461A GB1193461A GB2105667A GB2105667A GB1193461A GB 1193461 A GB1193461 A GB 1193461A GB 2105667 A GB2105667 A GB 2105667A GB 2105667 A GB2105667 A GB 2105667A GB 1193461 A GB1193461 A GB 1193461A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- alkyl
- substituted
- halogen
- alkoxy
- 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
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical class C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 38
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical class 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 239000004480 active ingredient Substances 0.000 abstract 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003435 aroyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000001556 benzimidazoles Chemical class 0.000 abstract 2
- 125000004965 chloroalkyl group Chemical group 0.000 abstract 2
- -1 cyano, carbomethoxy Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 2
- 238000009472 formulation Methods 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 2
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 208000031888 Mycoses Diseases 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 235000013399 edible fruits Nutrition 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000012770 industrial material Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 230000009885 systemic effect Effects 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
- C07F9/65068—Five-membered rings having the nitrogen atoms in positions 1 and 3 condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- C07D235/22—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms directly attached to ring nitrogen atoms
-
- 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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- 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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,193,461. Pesticides containing benzimidazoles. E. I. DU PONT DE NEMOURS & CO. 5 May, 1967 [6 May, 19661, No. 21056/67. Heading ASE. [Also in Division C2] Fungicidal and mite-ovicidal compositions comprise as active ingredient one or more compounds of the general formula:- wherein R 1 is alkyl of 1-4 carbon atoms; R 2 is hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 2 to 6 carbon atoms or alkynyl of 2 to 6 carbon atoms; R 3 is hydrogen; alkyl of 1 to 18 carbon atoms; alkyl of 1 to 18 carbon atoms substituted by one or more of halogen, alkoxy of 1 to 4 carbon atoms, and alkoxycarlbonyl of 2 to 4 carbon atoms; alkenyl of 3 to 18 carbon atoms; alkynyl of 3 to 18 8 carbon atoms; cycloalkyl of 3 to 8 carbon atoms; cycloalkyl of 3 to 8 carbon atoms substituted by one or more of methyl, methoxy, and chlorine; aralkyl of 5 to 8 carbon atoms; cycloalkenyl of 4 to 8 carbon atoms; cycloalkyl-alkyl of 4 to 9 carbon atoms; cycloalkenyl-akyl of 5 to 9 carbon atoms; aralkyl of 5 to 8 carbon atoms substituted by one or more of alkyl of 1 to 4 carbon atoms, chloroalkyl of 1 to 4 carbon atoms, fluoroalkyl of I to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, cyano, carbomethoxy, alkylsulfonyl of 1 to 4 carbon atoms, and nitro; phenyl; phenyl substituted by one or more of alkyl of I to 4 carbon atoms, chloroalkyl of 1 to 4 carbon atoms, fluoroalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, cyano, carbomethoxy, carboethoxy, and nitro; alkylsulfonyl of 1 to 18 carbon atoms; phenylsulfonyl; phenylsulfonyl substituted )by one or more of alkyl of 1 to 4 carbon atoms, halogen, cyano, or carboethoxy; acyl of 1 to 18 carbon atoms; acyl of 1 to 18 carbon atoms substituted by one or more of halogen and alkoxy of 1 to 4 carbon atoms; aroyl of 6 to 10 carbon atoms; or aroyl of 6 to 10 carbon atoms substituted by one or more of alkyl of to 4 carbon atoms, halogen, nitro, alkylsulfonyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms; or R 2 and R 3 with the N atom which joins them can together be a ring of 2 to 8 carbon atoms and the nitrogen atom or a ring of 4 carbon atoms, an oxygen atom and .the nitrogen atom. 'The compositions, having a systemic action, are suitable for controlling many fungus diseases of fruits, tubers, seeds and other plant parts, and also for the protection of wood, fabric, fibre board. paper, other industrial materials and household articles against rot and discolouration. The formulations may contain other active ingredients (over 100 listed) in addition to conventional adjuvants and carriers. Specified formulations include mixtures of methyl 1-(heptylcarbamoyl)- or 1-(ethoxycarbonylmethylcarbamoyl)-2-benzimidazole carbamate with methoxychlor, while numerous compositions containing only the novel benzimidazoles as the active ingredients are detailed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54803466A | 1966-05-06 | 1966-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1193461A true GB1193461A (en) | 1970-06-03 |
Family
ID=24187140
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB88770A Expired GB1193462A (en) | 1966-05-06 | 1967-05-05 | Substituted 2-Aminobenzimidazoles |
| GB2105667A Expired GB1193461A (en) | 1966-05-06 | 1967-05-05 | Substituted 2-Aminobenzimidazoles |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB88770A Expired GB1193462A (en) | 1966-05-06 | 1967-05-05 | Substituted 2-Aminobenzimidazoles |
Country Status (8)
| Country | Link |
|---|---|
| CY (2) | CY630A (en) |
| DO (1) | DOP1967001364A (en) |
| ES (1) | ES339900A1 (en) |
| FI (1) | FI46581C (en) |
| GB (2) | GB1193462A (en) |
| GR (1) | GR34500B (en) |
| IL (1) | IL27824A (en) |
| NL (1) | NL136613C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0256789A1 (en) * | 1986-08-07 | 1988-02-24 | Her Majesty In Right Of Canada As Represented By The Minister Of Agriculture | Substituted benzimidazole fungicide |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4078070A (en) * | 1973-01-16 | 1978-03-07 | Hoechst Aktiengesellschaft | Fungicidal dispersions |
| OA05041A (en) | 1974-07-15 | 1980-12-31 | Rhone Poulenc Ind | New fungicidal compositions. |
-
1967
- 1967-04-19 IL IL2782467A patent/IL27824A/en unknown
- 1967-04-27 GR GR670134500A patent/GR34500B/en unknown
- 1967-04-27 ES ES339900A patent/ES339900A1/en not_active Expired
- 1967-05-02 DO DO1967001364A patent/DOP1967001364A/en unknown
- 1967-05-05 GB GB88770A patent/GB1193462A/en not_active Expired
- 1967-05-05 NL NL6706331A patent/NL136613C/xx active
- 1967-05-05 FI FI130067A patent/FI46581C/en active
- 1967-05-05 GB GB2105667A patent/GB1193461A/en not_active Expired
-
1972
- 1972-02-14 CY CY63072A patent/CY630A/en unknown
- 1972-02-14 CY CY63172A patent/CY631A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0256789A1 (en) * | 1986-08-07 | 1988-02-24 | Her Majesty In Right Of Canada As Represented By The Minister Of Agriculture | Substituted benzimidazole fungicide |
Also Published As
| Publication number | Publication date |
|---|---|
| CY631A (en) | 1972-02-14 |
| GR34500B (en) | 1968-05-16 |
| NL6706331A (en) | 1967-11-07 |
| IL27824A (en) | 1971-04-28 |
| NL136613C (en) | 1973-01-16 |
| ES339900A1 (en) | 1968-09-16 |
| CY630A (en) | 1972-02-14 |
| FI46581B (en) | 1973-01-31 |
| DOP1967001364A (en) | 1972-03-29 |
| FI46581C (en) | 1973-05-08 |
| GB1193462A (en) | 1970-06-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 423P | Notice of intention to present a petition (sect. 23/1949) | ||
| 423P | Notice of intention to present a petition (sect. 23/1949) | ||
| EPO | Patent for which application for extension of term has been made to the comptroller or the court | ||
| 423X | Patent extended (sect. 23/1949) | ||
| 423X | Patent extended (sect. 23/1949) | ||
| EPF | Patent extended in pursuance of application for extension of term and in force | ||
| PE20 | Patent expired after termination of 20 years |