IL43513A - 1-alkoxycarbonyl-2-(bis-(alkoxycarbonyl)-amino)-benzimidazoles,their preparation and fungicidal and bactericidal compositions containing them - Google Patents
1-alkoxycarbonyl-2-(bis-(alkoxycarbonyl)-amino)-benzimidazoles,their preparation and fungicidal and bactericidal compositions containing themInfo
- Publication number
- IL43513A IL43513A IL7343513A IL4351373A IL43513A IL 43513 A IL43513 A IL 43513A IL 7343513 A IL7343513 A IL 7343513A IL 4351373 A IL4351373 A IL 4351373A IL 43513 A IL43513 A IL 43513A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- amino
- formula
- process according
- alkoxycarbonyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims 7
- 230000000844 anti-bacterial effect Effects 0.000 title claims 2
- 230000000855 fungicidal effect Effects 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 20
- 238000000034 method Methods 0.000 claims 17
- 150000003254 radicals Chemical class 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 5
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims 3
- 241000894006 Bacteria Species 0.000 claims 3
- 241000233866 Fungi Species 0.000 claims 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 239000002689 soil Substances 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Claims (29)
1. 1-Alkoxycarbon l-2-[' iB-(alkoxyca.rbonyl)-amino]-benzimidazoles of the general formula in which R is alkyl with 1-4 carbon atoms, it being possible for the radicals R to be different from one another or two or three radicals R to be identical.
2. Compounds according to claim 1, in which R is methyl, ethyl, n-propyl, iac ropyl or n-butyl.
3. The · compound of the formula
4. The compound of the formula
5. The compound of the formula Le A ,14 663 - 33 -
6. The compound of the formula
7. The compound
8. The compound of the formula
9. A process for the preparation of a 1-alkoxycarbonyl-2-[bis-(alkoxycarbonyl) -amino ]-benzimidazole according to any of claims 1 to 8,in which a 2-amino-benz imidazole of the general formula in which R 1 and R2 are each hydrogen or a -COOR radical, • and R has the meaning stated in cl im 1, is reacted with a carbonic acid derivative of the general formula .' . . / ■ X-COOR (III), in which X is halogen or an -0-COOR radical, and R has the meaning stated in claim 1, optionally in the presence of a diluent and optionally in the presence of an acid-binding agent.
10. A process according to claim 9, in which X is chlorine.
11. A process according to claim 9 or 10, in which the reaction is effected in an inert polar solvent.
12. A process according to claim 11, in which the solvent is pyridine.
13. A process according to any of claims 9 to 12, in which the reaction is effected at from -10° to +1O0°C.
14. A process according to claim 13, in which the reaction is effected at from 10° to 50°C.
15. A process according to any of claims 9 to 1 , in which the 2-amino-benzimidazole (II) is one that is hereinbefore specifically named.
16. A process according to any of claims 9 to 15» in which the carbonic acid derivative (III) is one that is hereinbefore specifically named.
17. A process according to any of claims 9 to 16, in which the 2-amino-benzimidazole (II) and carbonic acid derivative 1 2 (III) are used in a molar ratio of 1:3 - 4.5 (when R and R are both hydrogen)., 1:2 -3*.5 (when either R or.R is a -C00R radical) or 1:1-2.5 (when R1 and R2 are both -C00R radicals) .
18. A process for the preparation of a compound according to claim 1, substantially as hereinbefore described in any of Examples 1 to 5·
19. Compounds according to claim .1, whenever prepared by a process accordin to any of claims 9 to.18. - -
20. A fungicidal or bactericidal composition containing as active ingredient a compound according to any of claims. 1 to 5 and 19 in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
21. A composition according to claim 20 containing from 0.1 to 95$ of the active compound, "by weight.
22. A composition according to claim 21 containing from 0.5 to 90$ of the active compound,. by weight.
23. A method of combating fungi or bacteria which comprises applying to the fungi or bacteria or a habitat thereof. a compound according to any of claims 1 to 8 and 19 alone or in the form of a composition containing as active ingredient a compound according to any of claims 1 to 8 and 19 in admixture with a diluent or carrier.
24. A method according to claim 23 in which a composition is used containing from 0.0001 to of the active compound, by weight.
25. A method according to claim 24 in which a composition is used containing from 0.01 to 1 of the active compound, by weight. ..
26. A method according to any of claims 23 to 25 in which the active compound is applied to seed in an amount of 0.1 to 10 g per kg of seed.
27. ,27. A method according to any of claims 23 to 24 in which the active compound is applied to soil in an amount of 1 to 500 g per cubic metre of soil.
28. A method according to any of claims 23 to 27 in which the active compound is one of those hereinbefore mentioned in any of Examples A to H.
29. Crops protected from damage by fungi or bacteria by being grown in areas in which i mediately prior to and/or during the time of the growing a compound according to any of claims 1 to 8 and 19 was applied alone or in admixture with a diluent or carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2253324A DE2253324A1 (en) | 1972-10-31 | 1972-10-31 | 1-ALKOXYCARBONYL-2-SQUARE BRACKETS ON UP- (ALKOXYCARBONYL) -AMINO SQUARE BRACKETS FOR -BENZIMIDAZOLE, THE PROCESS FOR THEIR PRODUCTION AND THEIR USE AS FUNGICIDES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43513A0 IL43513A0 (en) | 1974-01-14 |
| IL43513A true IL43513A (en) | 1976-04-30 |
Family
ID=5860493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL7343513A IL43513A (en) | 1972-10-31 | 1973-10-29 | 1-alkoxycarbonyl-2-(bis-(alkoxycarbonyl)-amino)-benzimidazoles,their preparation and fungicidal and bactericidal compositions containing them |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | USB407014I5 (en) |
| BE (1) | BE806728A (en) |
| BR (1) | BR7308509D0 (en) |
| CH (1) | CH559186A5 (en) |
| DE (1) | DE2253324A1 (en) |
| DK (1) | DK133376B (en) |
| FR (1) | FR2204629B1 (en) |
| GB (1) | GB1397886A (en) |
| IE (1) | IE38437B1 (en) |
| IL (1) | IL43513A (en) |
| LU (1) | LU68711A1 (en) |
| NL (1) | NL7314835A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9205368D0 (en) * | 1992-03-12 | 1992-04-22 | Pfizer Ltd | Benzimidozole anthelmintic agents |
| US6479526B1 (en) | 1995-04-12 | 2002-11-12 | The Procter & Gamble Company | Pharmaceutical composition for inhibiting the growth of viruses and cancers |
| US6506783B1 (en) | 1997-05-16 | 2003-01-14 | The Procter & Gamble Company | Cancer treatments and pharmaceutical compositions therefor |
| US6423734B1 (en) | 1999-08-13 | 2002-07-23 | The Procter & Gamble Company | Method of preventing cancer |
| US6380232B1 (en) | 2000-09-26 | 2002-04-30 | The Procter & Gamble Company | Benzimidazole urea derivatives, and pharmaceutical compositions and unit dosages thereof |
| JP2004509949A (en) * | 2000-09-26 | 2004-04-02 | ザ ユニバーシティ オブ アリゾナ ファウンデーション | Compounds and methods for their use in treating cancer or viral infections |
| US6462062B1 (en) | 2000-09-26 | 2002-10-08 | The Procter & Gamble Company | Compounds and methods for use thereof in the treatment of cancer or viral infections |
| US6608096B1 (en) | 2000-09-26 | 2003-08-19 | University Of Arizona Foundation | Compounds and methods for use thereof in the treatment of cancer or viral infections |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1521994A (en) * | 1966-05-06 | 1968-04-19 | Du Pont | Use of esters of benzimidazolecarbamic acid as agents for destroying the eggs of mites |
-
1972
- 1972-10-31 DE DE2253324A patent/DE2253324A1/en active Pending
-
1973
- 1973-10-16 US US40701473 patent/USB407014I5/en active Pending
- 1973-10-29 NL NL7314835A patent/NL7314835A/xx unknown
- 1973-10-29 CH CH1522573A patent/CH559186A5/xx not_active IP Right Cessation
- 1973-10-29 LU LU68711A patent/LU68711A1/xx unknown
- 1973-10-29 IL IL7343513A patent/IL43513A/en unknown
- 1973-10-30 BR BR8509/73A patent/BR7308509D0/en unknown
- 1973-10-30 GB GB5035773A patent/GB1397886A/en not_active Expired
- 1973-10-30 BE BE137245A patent/BE806728A/en unknown
- 1973-10-30 DK DK586773AA patent/DK133376B/en unknown
- 1973-10-30 IE IE1952/73A patent/IE38437B1/en unknown
- 1973-10-31 FR FR7338826A patent/FR2204629B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE806728A (en) | 1974-04-30 |
| IE38437B1 (en) | 1978-03-15 |
| CH559186A5 (en) | 1975-02-28 |
| IL43513A0 (en) | 1974-01-14 |
| FR2204629B1 (en) | 1977-05-27 |
| USB407014I5 (en) | 1976-03-16 |
| NL7314835A (en) | 1974-05-02 |
| FR2204629A1 (en) | 1974-05-24 |
| BR7308509D0 (en) | 1974-08-15 |
| DK133376B (en) | 1976-05-10 |
| GB1397886A (en) | 1975-06-18 |
| DE2253324A1 (en) | 1974-05-09 |
| LU68711A1 (en) | 1974-01-08 |
| IE38437L (en) | 1974-04-30 |
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