DE2230182A1 - Neue benzimidazole - Google Patents
Neue benzimidazoleInfo
- Publication number
- DE2230182A1 DE2230182A1 DE2230182A DE2230182A DE2230182A1 DE 2230182 A1 DE2230182 A1 DE 2230182A1 DE 2230182 A DE2230182 A DE 2230182A DE 2230182 A DE2230182 A DE 2230182A DE 2230182 A1 DE2230182 A1 DE 2230182A1
- Authority
- DE
- Germany
- Prior art keywords
- plants
- infected
- active ingredient
- compounds
- infestation
- 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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title 1
- 239000004480 active ingredient Substances 0.000 claims description 31
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001556 benzimidazoles Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000575 pesticide Substances 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
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 27
- 206010061217 Infestation Diseases 0.000 description 23
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 19
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000007921 spray Substances 0.000 description 12
- 241000209140 Triticum Species 0.000 description 10
- 235000021307 Triticum Nutrition 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000011534 incubation Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 241000221785 Erysiphales Species 0.000 description 7
- -1 bidecylamine Chemical compound 0.000 description 7
- 102000006835 Lamins Human genes 0.000 description 6
- 108010047294 Lamins Proteins 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 210000005053 lamin Anatomy 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 238000005507 spraying Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000005789 Folpet Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- HSUGDXPUFCVGES-UHFFFAOYSA-N n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCNCCCCCCCCCCCCCC HSUGDXPUFCVGES-UHFFFAOYSA-N 0.000 description 4
- 244000052769 pathogen Species 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 241000233679 Peronosporaceae Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001157813 Cercospora Species 0.000 description 2
- 241000489964 Fusicladium Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000896238 Oidium Species 0.000 description 2
- 241000233614 Phytophthora Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 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
- 235000013339 cereals Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 231100000676 disease causative agent Toxicity 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- NQYKSVOHDVVDOR-UHFFFAOYSA-N n-hexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCC NQYKSVOHDVVDOR-UHFFFAOYSA-N 0.000 description 2
- YDFFPEXFCAUTSL-UHFFFAOYSA-N n-pentadecylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNCCCCCCCCCCCCCCC YDFFPEXFCAUTSL-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000725 suspension Substances 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
- 238000011179 visual inspection Methods 0.000 description 2
- JTQQDDNCCLCMER-CLFAGFIQSA-N (z)-n-[(z)-octadec-9-enyl]octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCCCCCCC\C=C/CCCCCCCC JTQQDDNCCLCMER-CLFAGFIQSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BCKYDNXQBUZUDJ-UHFFFAOYSA-N 2,4,4-trimethyl-n-(2,4,4-trimethylpentan-2-yl)pentan-2-amine Chemical compound CC(C)(C)CC(C)(C)NC(C)(C)CC(C)(C)C BCKYDNXQBUZUDJ-UHFFFAOYSA-N 0.000 description 1
- GUBPKKGRODRXPY-UHFFFAOYSA-N 3-(octadecylamino)propanenitrile Chemical compound CCCCCCCCCCCCCCCCCCNCCC#N GUBPKKGRODRXPY-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- KHFRJOPGKUBZLL-UHFFFAOYSA-N 7-methyl-n-(7-methyloctyl)octan-1-amine Chemical compound CC(C)CCCCCCNCCCCCCC(C)C KHFRJOPGKUBZLL-UHFFFAOYSA-N 0.000 description 1
- NOWPHMVQMCHHOZ-UHFFFAOYSA-N 7-methyl-n-propyloctan-1-amine Chemical compound CCCNCCCCCCC(C)C NOWPHMVQMCHHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000222290 Cladosporium Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001300479 Macroptilium Species 0.000 description 1
- 244000081841 Malus domestica Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000131448 Mycosphaerella Species 0.000 description 1
- NKGSHSILLGXYDW-UHFFFAOYSA-N N-undecylundecan-1-amine Chemical compound CCCCCCCCCCCNCCCCCCCCCCC NKGSHSILLGXYDW-UHFFFAOYSA-N 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
- 241000222291 Passalora fulva Species 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 241001533598 Septoria Species 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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 241000514371 Ustilago avenae Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 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
- 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
- 238000009835 boiling Methods 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000012677 causal agent Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 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
- ZQXDUKMRLYGEHT-UHFFFAOYSA-N ethene hydrochloride Chemical compound Cl.C=C.C=C ZQXDUKMRLYGEHT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- ZLOIOBQMTBIYOT-UHFFFAOYSA-N n-(7-methyloctyl)cyclohexanamine Chemical compound CC(C)CCCCCCNC1CCCCC1 ZLOIOBQMTBIYOT-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
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- 210000001519 tissue Anatomy 0.000 description 1
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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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2230182A DE2230182A1 (de) | 1972-06-21 | 1972-06-21 | Neue benzimidazole |
| ZA734064A ZA734064B (en) | 1972-06-21 | 1973-06-15 | Novel benzimidazoles |
| NL7308356A NL7308356A (enExample) | 1972-06-21 | 1973-06-15 | |
| BR4535/73A BR7304535D0 (pt) | 1972-06-21 | 1973-06-18 | Processo para a obtencao de novos benzimidazois e composicoes pesticidas a base dos mesmos |
| CH881473A CH551748A (de) | 1972-06-21 | 1973-06-18 | Schaedlingsbekaempfungsmittel. |
| AU57072/73A AU5707273A (en) | 1972-06-21 | 1973-06-18 | Novel benzimidazoles |
| AT537073A AT324323B (de) | 1972-06-21 | 1973-06-19 | Verfahren zur herstellung neuer benzimidazolderivate |
| IL42540A IL42540A0 (en) | 1972-06-21 | 1973-06-19 | Novel benzimidazoles |
| LU67813A LU67813A1 (enExample) | 1972-06-21 | 1973-06-19 | |
| US371537A US3904621A (en) | 1972-06-21 | 1973-06-19 | Novel benzimidazoles |
| GB2900873A GB1377354A (en) | 1972-06-21 | 1973-06-19 | Benzimidazoles process for their preparation and compositions containing them |
| ZM102/73*UA ZM10273A1 (en) | 1972-06-21 | 1973-06-19 | Novel benzimidazoles |
| JP48068847A JPS4954536A (enExample) | 1972-06-21 | 1973-06-20 | |
| HUHO1582A HU167463B (enExample) | 1972-06-21 | 1973-06-20 | |
| DD171731A DD108296A5 (enExample) | 1972-06-21 | 1973-06-21 | |
| OA54941A OA04427A (fr) | 1972-06-21 | 1973-06-21 | Benzimidazoles utilisables comme agents fongicides et préparation de ces substances. |
| BE132524A BE801219A (fr) | 1972-06-21 | 1973-06-21 | Benzimidazoles utilisables comme agents fongicides et preparation de ces substances |
| FR7322688A FR2189065A1 (enExample) | 1972-06-21 | 1973-06-21 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2230182A DE2230182A1 (de) | 1972-06-21 | 1972-06-21 | Neue benzimidazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2230182A1 true DE2230182A1 (de) | 1974-01-31 |
Family
ID=5848294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2230182A Pending DE2230182A1 (de) | 1972-06-21 | 1972-06-21 | Neue benzimidazole |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3904621A (enExample) |
| JP (1) | JPS4954536A (enExample) |
| AT (1) | AT324323B (enExample) |
| AU (1) | AU5707273A (enExample) |
| BE (1) | BE801219A (enExample) |
| BR (1) | BR7304535D0 (enExample) |
| CH (1) | CH551748A (enExample) |
| DD (1) | DD108296A5 (enExample) |
| DE (1) | DE2230182A1 (enExample) |
| FR (1) | FR2189065A1 (enExample) |
| GB (1) | GB1377354A (enExample) |
| HU (1) | HU167463B (enExample) |
| IL (1) | IL42540A0 (enExample) |
| LU (1) | LU67813A1 (enExample) |
| NL (1) | NL7308356A (enExample) |
| OA (1) | OA04427A (enExample) |
| ZA (1) | ZA734064B (enExample) |
| ZM (1) | ZM10273A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014443A1 (de) * | 1979-02-06 | 1980-08-20 | Riedel-De Haen Aktiengesellschaft | Verdünnbare Benzimidazolcarbaminsäurealkylester-Formulierung, Verfahren zu ihrer Herstellung und ihre Verwendung als Biozid |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2443297A1 (de) * | 1974-09-10 | 1976-03-18 | Hoechst Ag | Anthelminthisch wirksame basisch substituierte 2-carbalkoxy-amino-benzimidazolyl-5(6)-phenylaether und -ketone sowie verfahren zu ihrer herstellung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1523597A (fr) * | 1966-05-06 | 1968-05-03 | Du Pont | 2-aminobenzimidazoles substitués |
-
1972
- 1972-06-21 DE DE2230182A patent/DE2230182A1/de active Pending
-
1973
- 1973-06-15 NL NL7308356A patent/NL7308356A/xx unknown
- 1973-06-15 ZA ZA734064A patent/ZA734064B/xx unknown
- 1973-06-18 BR BR4535/73A patent/BR7304535D0/pt unknown
- 1973-06-18 AU AU57072/73A patent/AU5707273A/en not_active Expired
- 1973-06-18 CH CH881473A patent/CH551748A/xx not_active IP Right Cessation
- 1973-06-19 LU LU67813A patent/LU67813A1/xx unknown
- 1973-06-19 US US371537A patent/US3904621A/en not_active Expired - Lifetime
- 1973-06-19 IL IL42540A patent/IL42540A0/xx unknown
- 1973-06-19 ZM ZM102/73*UA patent/ZM10273A1/xx unknown
- 1973-06-19 GB GB2900873A patent/GB1377354A/en not_active Expired
- 1973-06-19 AT AT537073A patent/AT324323B/de not_active IP Right Cessation
- 1973-06-20 HU HUHO1582A patent/HU167463B/hu unknown
- 1973-06-20 JP JP48068847A patent/JPS4954536A/ja active Pending
- 1973-06-21 OA OA54941A patent/OA04427A/xx unknown
- 1973-06-21 BE BE132524A patent/BE801219A/xx unknown
- 1973-06-21 DD DD171731A patent/DD108296A5/xx unknown
- 1973-06-21 FR FR7322688A patent/FR2189065A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0014443A1 (de) * | 1979-02-06 | 1980-08-20 | Riedel-De Haen Aktiengesellschaft | Verdünnbare Benzimidazolcarbaminsäurealkylester-Formulierung, Verfahren zu ihrer Herstellung und ihre Verwendung als Biozid |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2189065A1 (enExample) | 1974-01-25 |
| JPS4954536A (enExample) | 1974-05-27 |
| AU5707273A (en) | 1974-12-19 |
| AT324323B (de) | 1975-08-25 |
| US3904621A (en) | 1975-09-09 |
| ZM10273A1 (en) | 1974-04-22 |
| BE801219A (fr) | 1973-12-21 |
| OA04427A (fr) | 1980-02-29 |
| BR7304535D0 (pt) | 1974-08-15 |
| NL7308356A (enExample) | 1973-12-27 |
| IL42540A0 (en) | 1973-08-29 |
| ZA734064B (en) | 1974-04-24 |
| HU167463B (enExample) | 1975-10-28 |
| GB1377354A (en) | 1974-12-11 |
| DD108296A5 (enExample) | 1974-09-12 |
| LU67813A1 (enExample) | 1975-03-27 |
| CH551748A (de) | 1974-07-31 |
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