NO115792B - - Google Patents
Info
- Publication number
- NO115792B NO115792B NO161767A NO16176766A NO115792B NO 115792 B NO115792 B NO 115792B NO 161767 A NO161767 A NO 161767A NO 16176766 A NO16176766 A NO 16176766A NO 115792 B NO115792 B NO 115792B
- Authority
- NO
- Norway
- Prior art keywords
- trifluoromethylbenzimidazole
- trichloro
- benzimidazole
- compounds
- substituted
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 230000000895 acaricidal effect Effects 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- -1 benzimidazole compound Chemical class 0.000 description 22
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- 230000004580 weight loss Effects 0.000 description 7
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- QECRKWYIIQPMPA-UHFFFAOYSA-N 4,7-dichloro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=CC(Cl)=C2NC(C(F)(F)F)=NC2=C1Cl QECRKWYIIQPMPA-UHFFFAOYSA-N 0.000 description 5
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- DYLHVMDRWJVLSN-UHFFFAOYSA-N 4,7-dibromo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=CC(Br)=C2NC(C(F)(F)F)=NC2=C1Br DYLHVMDRWJVLSN-UHFFFAOYSA-N 0.000 description 4
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- GYDGKROMMMZLQI-UHFFFAOYSA-N 4,6,7-tribromo-2-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(Br)C(Br)=C2NC(C(F)(F)F)=NC2=C1Br GYDGKROMMMZLQI-UHFFFAOYSA-N 0.000 description 3
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- USUPLSWSXSTERT-UHFFFAOYSA-N 6-bromo-4-nitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC(Br)=CC2=C1N=C(C(F)(F)F)N2 USUPLSWSXSTERT-UHFFFAOYSA-N 0.000 description 3
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- 230000009193 crawling Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- OJLOUXPPKZRTHK-UHFFFAOYSA-N dodecan-1-ol;sodium Chemical compound [Na].CCCCCCCCCCCCO OJLOUXPPKZRTHK-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 208000028454 lice infestation Diseases 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- IMYWCMHDHSHOTP-UHFFFAOYSA-N phenyl 4,5,6-trichloro-2-(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound C(=O)(OC1=CC=CC=C1)N1C(=NC2=C1C=C(C(=C2Cl)Cl)Cl)C(F)(F)F IMYWCMHDHSHOTP-UHFFFAOYSA-N 0.000 description 1
- ORUAHMUSMSOVBM-UHFFFAOYSA-N phenyl 6-chloro-4-nitro-2-(trifluoromethyl)benzimidazole-1-carboxylate Chemical compound FC(F)(F)C1=NC=2C([N+](=O)[O-])=CC(Cl)=CC=2N1C(=O)OC1=CC=CC=C1 ORUAHMUSMSOVBM-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229950000975 salicylanilide Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- D06M16/006—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic with wool-protecting agents; with anti-moth agents
-
- 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)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7680/65A GB1145011A (en) | 1965-02-23 | 1965-02-23 | 2-perfluoroalkylbenzimidazoles and their use as insecticides |
| GB920865 | 1965-03-04 | ||
| GB2958665 | 1965-07-13 | ||
| GB3288465 | 1965-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115792B true NO115792B (forum.php) | 1968-12-02 |
Family
ID=27447599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO161767A NO115792B (forum.php) | 1965-02-23 | 1966-02-18 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3542923A (forum.php) |
| BE (1) | BE676952A (forum.php) |
| BR (1) | BR6677145D0 (forum.php) |
| CH (2) | CH477816A (forum.php) |
| DE (1) | DE1670671A1 (forum.php) |
| DK (1) | DK119237B (forum.php) |
| ES (1) | ES323401A1 (forum.php) |
| FI (1) | FI42485B (forum.php) |
| FR (1) | FR1481098A (forum.php) |
| GB (2) | GB1145011A (forum.php) |
| IL (1) | IL25168A (forum.php) |
| NL (1) | NL6602316A (forum.php) |
| NO (1) | NO115792B (forum.php) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4122184A (en) * | 1973-09-14 | 1978-10-24 | Eli Lilly And Company | Benzimidazole insecticides |
| US4002623A (en) * | 1974-08-07 | 1977-01-11 | Pfizer Inc. | Anti-inflammatory 1-[3-(dialkylamino)propyl]-2-acylaminobenzimidazoles and 2-acylamino-3-[3-(dialkylamino)-propyl]imidazo[4,5-b]pyridines |
| US3980784A (en) * | 1974-12-02 | 1976-09-14 | Eli Lilly And Company | Control of animal parasites with benzimidazoles |
-
1965
- 1965-02-23 GB GB7680/65A patent/GB1145011A/en not_active Expired
- 1965-02-23 GB GB47324/68A patent/GB1144620A/en not_active Expired
-
1966
- 1966-02-14 IL IL25168A patent/IL25168A/en unknown
- 1966-02-14 BR BR177145/66A patent/BR6677145D0/pt unknown
- 1966-02-17 DE DE19661670671 patent/DE1670671A1/de active Pending
- 1966-02-18 NO NO161767A patent/NO115792B/no unknown
- 1966-02-18 FI FI0400/66A patent/FI42485B/fi active
- 1966-02-22 FR FR50515A patent/FR1481098A/fr not_active Expired
- 1966-02-22 ES ES0323401A patent/ES323401A1/es not_active Expired
- 1966-02-22 DK DK91366AA patent/DK119237B/da unknown
- 1966-02-23 CH CH260766A patent/CH477816A/fr not_active IP Right Cessation
- 1966-02-23 BE BE676952D patent/BE676952A/xx unknown
- 1966-02-23 CH CH773766A patent/CH467579A/fr unknown
- 1966-02-23 US US529248A patent/US3542923A/en not_active Expired - Lifetime
- 1966-02-23 NL NL6602316A patent/NL6602316A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES323401A1 (es) | 1967-02-01 |
| BE676952A (forum.php) | 1966-08-23 |
| CH260766A4 (forum.php) | 1969-05-30 |
| BR6677145D0 (pt) | 1973-09-18 |
| US3542923A (en) | 1970-11-24 |
| GB1144620A (en) | 1969-03-05 |
| GB1145011A (en) | 1969-03-12 |
| IL25168A (en) | 1970-02-19 |
| FI42485B (forum.php) | 1970-04-30 |
| CH477816A (fr) | 1969-10-31 |
| NL6602316A (forum.php) | 1966-08-24 |
| CH467579A (fr) | 1969-01-31 |
| FR1481098A (fr) | 1967-05-19 |
| DK119237B (da) | 1970-11-30 |
| DE1670671A1 (de) | 1970-12-03 |
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