IL33340A - Metal complexes of 2-benzimidazolecarbamic acid esters their preparation and use as fungicides - Google Patents
Metal complexes of 2-benzimidazolecarbamic acid esters their preparation and use as fungicidesInfo
- Publication number
- IL33340A IL33340A IL33340A IL3334069A IL33340A IL 33340 A IL33340 A IL 33340A IL 33340 A IL33340 A IL 33340A IL 3334069 A IL3334069 A IL 3334069A IL 33340 A IL33340 A IL 33340A
- Authority
- IL
- Israel
- Prior art keywords
- complexes
- acid
- complex
- parts
- zinc
- Prior art date
Links
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 title description 24
- 238000002360 preparation method Methods 0.000 title description 14
- 229910052751 metal Inorganic materials 0.000 title description 9
- 239000002184 metal Substances 0.000 title description 9
- 239000000417 fungicide Substances 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 18
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052802 copper Inorganic materials 0.000 claims description 13
- 239000010949 copper Substances 0.000 claims description 13
- 239000011701 zinc Substances 0.000 claims description 13
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 229910052725 zinc Inorganic materials 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 45
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 39
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 34
- -1 Alkyl 2-benzimidazole carbamates Chemical class 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 29
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- 239000004094 surface-active agent Substances 0.000 description 26
- 239000002253 acid Substances 0.000 description 25
- 239000008187 granular material Substances 0.000 description 23
- 241000233866 Fungi Species 0.000 description 21
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- 239000011592 zinc chloride Substances 0.000 description 20
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- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 10
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- 244000070406 Malus silvestris Species 0.000 description 7
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- VNDYJBBGRKZCSX-UHFFFAOYSA-L Zinc bromide Inorganic materials Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 5
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- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
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- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 3
- 241000167854 Bourreria succulenta Species 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- LZIMCAJYEGJUFV-UHFFFAOYSA-M CCC(=O)O[Zn] Chemical compound CCC(=O)O[Zn] LZIMCAJYEGJUFV-UHFFFAOYSA-M 0.000 description 3
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- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 3
- AIGRXSNSLVJMEA-UHFFFAOYSA-N EPN Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-UHFFFAOYSA-N 0.000 description 3
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- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011268 retreatment Methods 0.000 description 1
- JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- JJSYXNQGLHBRRK-SFEDZAPPSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-SFEDZAPPSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940045998 sodium isethionate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
- VYKNIXCUMQEUCK-UHFFFAOYSA-M sodium;acetic acid;dodecyl sulfate Chemical compound [Na+].CC(O)=O.CCCCCCCCCCCCOS([O-])(=O)=O VYKNIXCUMQEUCK-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- KRTNITDCKAVIFI-UHFFFAOYSA-N tridecyl benzenesulfonate Chemical class CCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 KRTNITDCKAVIFI-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77717168A | 1968-11-19 | 1968-11-19 | |
| US86823369A | 1969-10-21 | 1969-10-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33340A0 IL33340A0 (en) | 1970-03-22 |
| IL33340A true IL33340A (en) | 1972-09-28 |
Family
ID=27119291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33340A IL33340A (en) | 1968-11-19 | 1969-11-10 | Metal complexes of 2-benzimidazolecarbamic acid esters their preparation and use as fungicides |
Country Status (15)
| Country | Link |
|---|---|
| AR (1) | AR201077A1 (fr) |
| BE (1) | BE741574A (fr) |
| CH (1) | CH532893A (fr) |
| DE (1) | DE1957712A1 (fr) |
| DK (1) | DK131856C (fr) |
| DO (1) | DOP1969001706A (fr) |
| ES (1) | ES373658A1 (fr) |
| FR (1) | FR2023630A1 (fr) |
| GB (1) | GB1268558A (fr) |
| IE (1) | IE33365B1 (fr) |
| IL (1) | IL33340A (fr) |
| MY (1) | MY7300261A (fr) |
| NL (1) | NL160257C (fr) |
| OA (1) | OA03173A (fr) |
| PH (1) | PH9996A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI119903B (fi) * | 2006-03-16 | 2009-05-15 | Kemira Oyj | Bakteeri-itiöiden muodostumisen estäminen kartonkikoneen hylkysysteemissä |
-
1969
- 1969-11-06 IE IE1516/69A patent/IE33365B1/xx unknown
- 1969-11-10 IL IL33340A patent/IL33340A/en unknown
- 1969-11-12 BE BE741574D patent/BE741574A/xx not_active IP Right Cessation
- 1969-11-14 DK DK605769A patent/DK131856C/da not_active IP Right Cessation
- 1969-11-14 CH CH1701069A patent/CH532893A/de not_active IP Right Cessation
- 1969-11-17 GB GB56180/69A patent/GB1268558A/en not_active Expired
- 1969-11-17 OA OA53786A patent/OA03173A/fr unknown
- 1969-11-17 DE DE19691957712 patent/DE1957712A1/de not_active Ceased
- 1969-11-18 FR FR6939685A patent/FR2023630A1/fr not_active Withdrawn
- 1969-11-18 DO DO1969001706A patent/DOP1969001706A/es unknown
- 1969-11-18 ES ES373658A patent/ES373658A1/es not_active Expired
- 1969-11-18 NL NL6917314.A patent/NL160257C/xx not_active IP Right Cessation
-
1970
- 1970-09-28 AR AR231507A patent/AR201077A1/es active
-
1972
- 1972-06-15 PH PH13626A patent/PH9996A/en unknown
-
1973
- 1973-12-30 MY MY261/73A patent/MY7300261A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| OA03173A (fr) | 1970-12-15 |
| MY7300261A (en) | 1973-12-31 |
| IL33340A0 (en) | 1970-03-22 |
| NL160257C (nl) | 1979-10-15 |
| GB1268558A (en) | 1972-03-29 |
| BE741574A (fr) | 1970-04-16 |
| NL6917314A (fr) | 1970-05-21 |
| DE1957712A1 (de) | 1970-06-18 |
| DK131856C (da) | 1976-02-16 |
| DOP1969001706A (es) | 1974-11-15 |
| CH532893A (de) | 1973-01-31 |
| ES373658A1 (es) | 1972-04-16 |
| FR2023630A1 (fr) | 1970-08-21 |
| AR201077A1 (es) | 1975-02-14 |
| IE33365B1 (en) | 1974-05-29 |
| NL160257B (nl) | 1979-05-15 |
| PH9996A (en) | 1976-07-13 |
| DK131856B (da) | 1975-09-15 |
| IE33365L (en) | 1970-05-19 |
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