GB1213796A - 0-substituted-2-haloalkyl-benzimidazoles and -imidazopyridines, and their use as pesticides - Google Patents
0-substituted-2-haloalkyl-benzimidazoles and -imidazopyridines, and their use as pesticidesInfo
- Publication number
- GB1213796A GB1213796A GB1720067A GB1720067A GB1213796A GB 1213796 A GB1213796 A GB 1213796A GB 1720067 A GB1720067 A GB 1720067A GB 1720067 A GB1720067 A GB 1720067A GB 1213796 A GB1213796 A GB 1213796A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- compounds
- substituted
- mono
- cyano
- 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
- 239000000575 pesticide Substances 0.000 title abstract 2
- -1 cyano, amino Chemical group 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001556 benzimidazoles Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000005283 haloketone group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 150000005232 imidazopyridines Chemical class 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000008301 phosphite esters Chemical class 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1,213,796. Benzimidazoles and imidazopyridines. SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ N.V. 4 March, 1968 [14 April, 1967], No. 17200/67. Heading C2C. [Also in Division A5] The invention comprises compounds of the general formula wherein A represents a nitrogen atom or a methine group -CH-; X represents a haloalkyl group; R represents a halogen atom or a nitro, alkyl, alkoxy, alkylthio, cyano, amino or mono- or di-substituted amino, or alkyl sulphonyl group; n has a value from 0-3 and when n is greater than 1 each group R may be the same or different; and Q represents a nitro group, or a group of the formula in which R 2 represents a divalent, saturated hydrocarbyl group, and Z represents a cyano, alkanoyl, cycloalkanoyloxy, mono-N-substituted carbamoyloxy, organophosphate or organophosphonate group. The compounds are obtained from compounds of the general formula by the following processes: (a) Q = -NO 2 ; by reaction with nitric acid in an organic diluent, e.g. acetic anhydride. (b) Q = -CH 2 -Z where Z represents cycloalkanoyloxy, mono-N-substituted carbamoyloxy, organophosphate or organophosphonate; by reaction with formalin to form the 1- methylol derivative, and subsequently reacting this compound with an isocyanate to form the N-substituted carbamoyloxy derivative or with a halogenating agent, such as phosphorus pentachloride, to form the 1-halomethyl derivative followed by an alkali metal salt, preferably the sodium salt, of the appropriate cycloalkanoic or organophosphoric acid, or followed by an organophosphite. (c) Q = -CH 2 -Z where Z represents cyano or alkanoyl; by reaction with sodium in the presence of an inert diluent, suitably dimethyl formamide, and subsequently reacting the resultant sodium salt with chloroacetonitrile or with an appropriate haloketone, preferably chloroacetone. The compounds of the invention are pesticides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1720067A GB1213796A (en) | 1967-04-14 | 1967-04-14 | 0-substituted-2-haloalkyl-benzimidazoles and -imidazopyridines, and their use as pesticides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1720067A GB1213796A (en) | 1967-04-14 | 1967-04-14 | 0-substituted-2-haloalkyl-benzimidazoles and -imidazopyridines, and their use as pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1213796A true GB1213796A (en) | 1970-11-25 |
Family
ID=10091001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1720067A Expired GB1213796A (en) | 1967-04-14 | 1967-04-14 | 0-substituted-2-haloalkyl-benzimidazoles and -imidazopyridines, and their use as pesticides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1213796A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0448206A2 (en) * | 1990-02-16 | 1991-09-25 | Zeneca Limited | Substituted benzimidazole and indazole derivatives, processes for their preparation and their use as herbicides |
| EP0597304A1 (en) * | 1992-11-06 | 1994-05-18 | Bayer Ag | Use of substituted benzimidazoles |
| US5656649A (en) * | 1992-11-06 | 1997-08-12 | Bayer Aktiengesellschaft | Substituted benzimidazoles |
| US5877195A (en) * | 1992-11-06 | 1999-03-02 | Bayer Aktiengesellschaft | 2-perhalogenalkyl-substituted benzimidazoles, and their use as pesticides |
-
1967
- 1967-04-14 GB GB1720067A patent/GB1213796A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0448206A2 (en) * | 1990-02-16 | 1991-09-25 | Zeneca Limited | Substituted benzimidazole and indazole derivatives, processes for their preparation and their use as herbicides |
| EP0448206A3 (en) * | 1990-02-16 | 1992-04-29 | Imperial Chemical Industries Plc | Substituted benzimidazole and indazole derivatives, processes for their preparation and their use as herbicides |
| US5306692A (en) * | 1990-02-16 | 1994-04-26 | Zeneca Limited | Herbicidal indazole and benzimidazole compounds |
| EP0597304A1 (en) * | 1992-11-06 | 1994-05-18 | Bayer Ag | Use of substituted benzimidazoles |
| US5482956A (en) * | 1992-11-06 | 1996-01-09 | Bayer Aktiengesellschaft | Method of treating parastic protozoa with substituted benzimidazoles |
| US5656649A (en) * | 1992-11-06 | 1997-08-12 | Bayer Aktiengesellschaft | Substituted benzimidazoles |
| US5863933A (en) * | 1992-11-06 | 1999-01-26 | Bayer Aktiengesellschaft | Substituted benzimidazoles |
| US5877195A (en) * | 1992-11-06 | 1999-03-02 | Bayer Aktiengesellschaft | 2-perhalogenalkyl-substituted benzimidazoles, and their use as pesticides |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |