DE2126838A1 - Neue Benzimidazole - Google Patents
Neue BenzimidazoleInfo
- Publication number
- DE2126838A1 DE2126838A1 DE19712126838 DE2126838A DE2126838A1 DE 2126838 A1 DE2126838 A1 DE 2126838A1 DE 19712126838 DE19712126838 DE 19712126838 DE 2126838 A DE2126838 A DE 2126838A DE 2126838 A1 DE2126838 A1 DE 2126838A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- chcl
- benzimidazoles
- cooch
- chci
- 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.)
- Pending
Links
- 150000001556 benzimidazoles Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 241000221785 Erysiphales Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- -1 however Chemical compound 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- RQIMPDXRFCFBGC-UHFFFAOYSA-N n-(oxomethylidene)sulfamoyl fluoride Chemical compound FS(=O)(=O)N=C=O RQIMPDXRFCFBGC-UHFFFAOYSA-N 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FSIKCOSQVQVZOF-UHFFFAOYSA-N 1,2-dichloro-n-(oxomethylidene)ethanesulfonamide Chemical compound ClCC(Cl)S(=O)(=O)N=C=O FSIKCOSQVQVZOF-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MWMBGFWXUXHCNF-UHFFFAOYSA-N 2,4,4-trichloro-n-(oxomethylidene)butane-1-sulfonamide Chemical compound ClC(Cl)CC(Cl)CS(=O)(=O)N=C=O MWMBGFWXUXHCNF-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- 241000222290 Cladosporium Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000222291 Passalora fulva Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000000344 soap Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712126838 DE2126838A1 (de) | 1971-05-29 | 1971-05-29 | Neue Benzimidazole |
| GB2449772A GB1334995A (en) | 1971-05-29 | 1972-05-24 | Benzimidazoles process for preparing them and preparations containing them |
| NL7206974A NL7206974A (enrdf_load_stackoverflow) | 1971-05-29 | 1972-05-24 | |
| ZA723542A ZA723542B (en) | 1971-05-29 | 1972-05-24 | Novel benzimidazoles and process for their preparation |
| CH761872A CH538247A (de) | 1971-05-29 | 1972-05-24 | Schädlingsbekämpfungsmittel, Verfahren zu seiner Herstellung und seine Verwendung |
| AT456272A AT318606B (de) | 1971-05-29 | 1972-05-26 | Verfahren zur Herstellung von neuen Benzimidazolderivaten |
| IL39545A IL39545A0 (en) | 1971-05-29 | 1972-05-26 | Novel benzimidazoles and process for their preparation |
| BE784126A BE784126A (fr) | 1971-05-29 | 1972-05-29 | Benzimidazoles, leur preparation et leurs |
| FR7219125A FR2140041B1 (enrdf_load_stackoverflow) | 1971-05-29 | 1972-05-29 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712126838 DE2126838A1 (de) | 1971-05-29 | 1971-05-29 | Neue Benzimidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2126838A1 true DE2126838A1 (de) | 1972-12-14 |
Family
ID=5809327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712126838 Pending DE2126838A1 (de) | 1971-05-29 | 1971-05-29 | Neue Benzimidazole |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT318606B (enrdf_load_stackoverflow) |
| BE (1) | BE784126A (enrdf_load_stackoverflow) |
| CH (1) | CH538247A (enrdf_load_stackoverflow) |
| DE (1) | DE2126838A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2140041B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1334995A (enrdf_load_stackoverflow) |
| IL (1) | IL39545A0 (enrdf_load_stackoverflow) |
| NL (1) | NL7206974A (enrdf_load_stackoverflow) |
| ZA (1) | ZA723542B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0073480A1 (de) * | 1981-09-01 | 1983-03-09 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von teilweise neuen 1,2-Dihalogenalkyl- und -cycloalkylsulfonylisocyanaten |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2257184A1 (de) * | 1972-11-22 | 1974-05-30 | Hoechst Ag | Neue benzimidazolverbindungen |
-
1971
- 1971-05-29 DE DE19712126838 patent/DE2126838A1/de active Pending
-
1972
- 1972-05-24 NL NL7206974A patent/NL7206974A/xx unknown
- 1972-05-24 GB GB2449772A patent/GB1334995A/en not_active Expired
- 1972-05-24 ZA ZA723542A patent/ZA723542B/xx unknown
- 1972-05-24 CH CH761872A patent/CH538247A/de not_active IP Right Cessation
- 1972-05-26 AT AT456272A patent/AT318606B/de not_active IP Right Cessation
- 1972-05-26 IL IL39545A patent/IL39545A0/xx unknown
- 1972-05-29 BE BE784126A patent/BE784126A/xx unknown
- 1972-05-29 FR FR7219125A patent/FR2140041B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0073480A1 (de) * | 1981-09-01 | 1983-03-09 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von teilweise neuen 1,2-Dihalogenalkyl- und -cycloalkylsulfonylisocyanaten |
Also Published As
| Publication number | Publication date |
|---|---|
| BE784126A (fr) | 1972-11-29 |
| FR2140041A1 (enrdf_load_stackoverflow) | 1973-01-12 |
| IL39545A0 (en) | 1972-07-26 |
| AT318606B (de) | 1974-11-11 |
| GB1334995A (en) | 1973-10-24 |
| CH538247A (de) | 1973-06-30 |
| ZA723542B (en) | 1973-03-28 |
| FR2140041B1 (enrdf_load_stackoverflow) | 1975-08-08 |
| NL7206974A (enrdf_load_stackoverflow) | 1972-12-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2638470C2 (enrdf_load_stackoverflow) | ||
| EP0277317B1 (de) | Nitro-Derivate von 2-Iminoimidazolidinen und 2-Iminotetrahydropyrimidinen | |
| DE2640823A1 (de) | 1,2,4-triazole, verfahren zur herstellung derselben, solche verbindungen enthaltende zusammensetzungen zur bekaempfung von schaedlingen und verfahren zur bekaempfung von schaedlingen | |
| DE2350123A1 (de) | 1-propyl-imidazolyl-derivate und deren salze, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| CH631710A5 (de) | Verfahren zur herstellung von neuen azolyl-carbonsaeure-derivaten. | |
| DE1542886A1 (de) | Fungizide Mittel | |
| DE1955750A1 (de) | Ureidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2801868C2 (de) | Benzthiazolon- und Benzoxazolon-Derivate | |
| DE2431073A1 (de) | Fungizides mittel | |
| DE1960029A1 (de) | Ureidophenylthioharnstoffe,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| EP0002679B1 (de) | 1-Halogen-1-propin-3-ole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| EP0000112B1 (de) | Triazolsubstituierte Schwefelverbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| DE2126838A1 (de) | Neue Benzimidazole | |
| DE2105174B2 (de) | 8-Oxychinolin- und 8-Oxy chinaldinacrylate, Verfahren zu ihrer Herstellung und Mittel zur Bekämpfung von Mikroorganismen | |
| EP0075172B1 (de) | N-Sulfenylierte Benzylsulfonamide, ein Verfahren und ihre Verwendung als Mikrobizide | |
| DE1300117B (de) | 5-Sulfonyl-1, 2-dithiol-3-one | |
| EP0033501A2 (de) | Beta-Imidazolylalkohole, Verfahren zu ihrer Herstellung, diese enthaltende Fungizide und Verfahren zur Bekämpfung von Pilzen mit ihnen | |
| DE1767924A1 (de) | 1-Phenyl-4,4-dialkyl-thiosemicarbazide | |
| DE2025412A1 (de) | Amidophenylisothiohamstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2536951A1 (de) | Triazapentadiene, verfahren zu ihrer herstellung und ihre verwendung als milbenmittel und insektizide | |
| DE2044205A1 (de) | Neue Benzimidazole | |
| EP0096280A2 (de) | Alkylen(cycloalkylen)-bis-heterocyclyl-biguanide | |
| EP0011802A1 (de) | Neue Phenoxy-phenoxypropionsäureamide, Verfahren zu ihrer Herstellung, sie enthaltende herbizide Mittel und ihre Verwendung zur Bekämpfung von Schadpflanzen | |
| EP0123179B1 (de) | Phosphorylierte Azolyl-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| DE2453210A1 (de) | Fungizides mittel |