FI59996C - Bensimidazol-1-karboximidsyraestrar anvaendbara i fungicider och insekticider - Google Patents
Bensimidazol-1-karboximidsyraestrar anvaendbara i fungicider och insekticider Download PDFInfo
- Publication number
- FI59996C FI59996C FI2841/74A FI284174A FI59996C FI 59996 C FI59996 C FI 59996C FI 2841/74 A FI2841/74 A FI 2841/74A FI 284174 A FI284174 A FI 284174A FI 59996 C FI59996 C FI 59996C
- Authority
- FI
- Finland
- Prior art keywords
- acid
- ester
- benzimidazole
- carboxyimidic
- methoxycarbonylamino
- Prior art date
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- 239000002253 acid Substances 0.000 claims description 335
- -1 dimethylphenyl Chemical group 0.000 claims description 198
- 150000002148 esters Chemical class 0.000 claims description 183
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000000417 fungicide Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
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- 125000006004 trihaloethyl group Chemical group 0.000 claims description 2
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- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 99
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- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- 241000514371 Ustilago avenae Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- XKAFBNIWKRVUHR-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl] 2-(methoxycarbonylamino)benzimidazole-1-carboximidate Chemical compound COC(=O)NC1=NC2=CC=CC=C2N1C(=N)OC1=CC=CC(C(F)(F)F)=C1 XKAFBNIWKRVUHR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-M benzenecarboximidate Chemical compound [NH-]C(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-M 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- JZRIIAYLOPWOHN-UHFFFAOYSA-N benzimidazole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)C=NC2=C1 JZRIIAYLOPWOHN-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KDJVUTSOHYQCDQ-UHFFFAOYSA-N carbamic acid;1h-imidazole Chemical compound NC([O-])=O.[NH2+]1C=CN=C1 KDJVUTSOHYQCDQ-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DVGSPWWRHYNDOM-UHFFFAOYSA-N ethyl N-(1-carbamoylbenzimidazol-2-yl)carbamate Chemical compound C(N)(=O)N1C(NC2=C1C=CC=C2)=NC(=O)OCC DVGSPWWRHYNDOM-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- CLIDMUTWHLMPMN-UHFFFAOYSA-N imidazole-1-carboxamide Chemical compound NC(=O)N1C=CN=C1 CLIDMUTWHLMPMN-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- OLHMAYWCOLTPGR-UHFFFAOYSA-N naphthalen-2-yl 2-(methoxycarbonylamino)benzimidazole-1-carboximidate Chemical compound C1=CC=CC2=CC(OC(=N)N3C4=CC=CC=C4N=C3NC(=O)OC)=CC=C21 OLHMAYWCOLTPGR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- CWHFDTWZHFRTAB-UHFFFAOYSA-N phenyl cyanate Chemical compound N#COC1=CC=CC=C1 CWHFDTWZHFRTAB-UHFFFAOYSA-N 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07D235/24—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732349919 DE2349919A1 (de) | 1973-10-02 | 1973-10-02 | Benzimidazol-l-carboximidsaeureester |
| DE2349919 | 1973-10-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI284174A7 FI284174A7 (en, 2012) | 1975-04-03 |
| FI59996B FI59996B (fi) | 1981-07-31 |
| FI59996C true FI59996C (fi) | 1981-11-10 |
Family
ID=5894550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2841/74A FI59996C (fi) | 1973-10-02 | 1974-09-27 | Bensimidazol-1-karboximidsyraestrar anvaendbara i fungicider och insekticider |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3956307A (en, 2012) |
| JP (1) | JPS5534767B2 (en, 2012) |
| AR (1) | AR208891A1 (en, 2012) |
| AT (1) | AT337498B (en, 2012) |
| BE (1) | BE820633A (en, 2012) |
| BR (1) | BR7408136D0 (en, 2012) |
| CA (1) | CA1040204A (en, 2012) |
| CH (1) | CH602662A5 (en, 2012) |
| CS (1) | CS177883B2 (en, 2012) |
| DD (1) | DD113990A5 (en, 2012) |
| DE (1) | DE2349919A1 (en, 2012) |
| DK (1) | DK518474A (en, 2012) |
| ES (1) | ES430630A1 (en, 2012) |
| FI (1) | FI59996C (en, 2012) |
| FR (1) | FR2246549B1 (en, 2012) |
| GB (1) | GB1485307A (en, 2012) |
| HU (1) | HU170903B (en, 2012) |
| IE (1) | IE39924B1 (en, 2012) |
| IL (1) | IL45751A (en, 2012) |
| IT (1) | IT1049316B (en, 2012) |
| LU (1) | LU71022A1 (en, 2012) |
| NL (1) | NL7413038A (en, 2012) |
| NO (1) | NO140590C (en, 2012) |
| PH (1) | PH11025A (en, 2012) |
| PL (1) | PL94342B1 (en, 2012) |
| RO (1) | RO63912A2 (en, 2012) |
| SE (1) | SE7412061L (en, 2012) |
| SU (3) | SU633447A3 (en, 2012) |
| TR (1) | TR18580A (en, 2012) |
| YU (1) | YU258774A (en, 2012) |
| ZA (1) | ZA746281B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5952870U (ja) * | 1982-09-30 | 1984-04-06 | 横山 禧一 | 鮎友釣り用仕掛 |
| JPS606146A (ja) * | 1983-06-22 | 1985-01-12 | 中島 純一 | 鮎の友釣仕掛 |
| JPH0367577U (en, 2012) * | 1989-11-02 | 1991-07-02 | ||
| DE19642529A1 (de) * | 1996-10-15 | 1998-04-16 | Bayer Ag | Aminophenolderivate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1523597A (fr) * | 1966-05-06 | 1968-05-03 | Du Pont | 2-aminobenzimidazoles substitués |
| US3626070A (en) * | 1968-03-20 | 1971-12-07 | Du Pont | Substituted 2-aminobenzimidazoles as anthelmintics |
| DE2012219A1 (de) * | 1970-03-14 | 1971-09-23 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Substituierte Benzimidazole |
| US3631176A (en) * | 1970-07-20 | 1971-12-28 | Du Pont | Carbamoyl substituted 2-aminobenzimidazoles |
-
1973
- 1973-10-02 DE DE19732349919 patent/DE2349919A1/de active Pending
-
1974
- 1974-08-29 CH CH1178574A patent/CH602662A5/xx not_active IP Right Cessation
- 1974-09-13 TR TR18580A patent/TR18580A/xx unknown
- 1974-09-25 YU YU02587/74A patent/YU258774A/xx unknown
- 1974-09-25 SE SE7412061A patent/SE7412061L/xx not_active Application Discontinuation
- 1974-09-26 CS CS6625A patent/CS177883B2/cs unknown
- 1974-09-27 FI FI2841/74A patent/FI59996C/fi active
- 1974-09-27 AT AT779974A patent/AT337498B/de not_active IP Right Cessation
- 1974-09-30 LU LU71022A patent/LU71022A1/xx unknown
- 1974-09-30 GB GB42462/74A patent/GB1485307A/en not_active Expired
- 1974-09-30 IL IL45751A patent/IL45751A/en unknown
- 1974-09-30 DD DD181407A patent/DD113990A5/xx unknown
- 1974-10-01 SU SU742063625A patent/SU633447A3/ru active
- 1974-10-01 IE IE2033/74A patent/IE39924B1/xx unknown
- 1974-10-01 HU HU74SC00000498A patent/HU170903B/hu unknown
- 1974-10-01 NO NO743555A patent/NO140590C/no unknown
- 1974-10-01 SU SU742063355A patent/SU651694A3/ru active
- 1974-10-01 BR BR8136/74A patent/BR7408136D0/pt unknown
- 1974-10-01 PH PH16359A patent/PH11025A/en unknown
- 1974-10-01 AR AR255870A patent/AR208891A1/es active
- 1974-10-01 IT IT27958/74A patent/IT1049316B/it active
- 1974-10-01 FR FR7432999A patent/FR2246549B1/fr not_active Expired
- 1974-10-01 US US05/511,092 patent/US3956307A/en not_active Expired - Lifetime
- 1974-10-01 RO RO80103A patent/RO63912A2/ro unknown
- 1974-10-02 NL NL7413038A patent/NL7413038A/xx not_active Application Discontinuation
- 1974-10-02 CA CA210,585A patent/CA1040204A/en not_active Expired
- 1974-10-02 DK DK518474A patent/DK518474A/da unknown
- 1974-10-02 ES ES430630A patent/ES430630A1/es not_active Expired
- 1974-10-02 BE BE149152A patent/BE820633A/xx unknown
- 1974-10-02 JP JP11369774A patent/JPS5534767B2/ja not_active Expired
- 1974-10-02 ZA ZA00746281A patent/ZA746281B/xx unknown
- 1974-10-02 PL PL1974174530A patent/PL94342B1/pl unknown
-
1976
- 1976-02-10 SU SU762322211A patent/SU644358A3/ru active
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