CH655311A5 - Imidazolyl-propionitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel und mittel mit wachstumsregulierender wirkung. - Google Patents
Imidazolyl-propionitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel und mittel mit wachstumsregulierender wirkung. Download PDFInfo
- Publication number
- CH655311A5 CH655311A5 CH3960/82A CH396082A CH655311A5 CH 655311 A5 CH655311 A5 CH 655311A5 CH 3960/82 A CH3960/82 A CH 3960/82A CH 396082 A CH396082 A CH 396082A CH 655311 A5 CH655311 A5 CH 655311A5
- Authority
- CH
- Switzerland
- Prior art keywords
- propionitrile
- imidazol
- plants
- chlorophenyl
- nitric acid
- Prior art date
Links
- 230000000694 effects Effects 0.000 title claims description 66
- 150000001875 compounds Chemical class 0.000 title claims description 52
- 238000000034 method Methods 0.000 title claims description 8
- PAPPEKHULAQSEJ-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)propanenitrile Chemical compound N#CC(C)C1=NC=CN1 PAPPEKHULAQSEJ-UHFFFAOYSA-N 0.000 title claims description 4
- 239000003139 biocide Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 QQ-alkylthio Chemical group 0.000 claims description 101
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 46
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- HPUFKQJSHDRFCT-UHFFFAOYSA-N 2-butoxy-2-(2-chlorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=C(C=CC=C1)Cl HPUFKQJSHDRFCT-UHFFFAOYSA-N 0.000 claims description 2
- BLTPCAGRXYBKBL-UHFFFAOYSA-N 2-butoxy-2-(4-chlorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=CC=C(C=C1)Cl BLTPCAGRXYBKBL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 50
- 239000004480 active ingredient Substances 0.000 description 28
- 238000011282 treatment Methods 0.000 description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 23
- 208000015181 infectious disease Diseases 0.000 description 23
- 230000000855 fungicidal effect Effects 0.000 description 21
- 241000209219 Hordeum Species 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 238000005507 spraying Methods 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 206010061217 Infestation Diseases 0.000 description 13
- 235000007340 Hordeum vulgare Nutrition 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000000069 prophylactic effect Effects 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000006378 damage Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000012010 growth Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000004563 wettable powder Substances 0.000 description 8
- 235000015097 nutrients Nutrition 0.000 description 7
- 230000008635 plant growth Effects 0.000 description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 5
- 241000233866 Fungi Species 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- 241001480061 Blumeria graminis Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010039509 Scab Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000010419 agar Nutrition 0.000 description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000021186 dishes Nutrition 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 244000052769 pathogen Species 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000190150 Bipolaris sorokiniana Species 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000211187 Lepidium sativum Species 0.000 description 3
- 235000007849 Lepidium sativum Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000589613 Pseudomonas savastanoi pv. phaseolicola Species 0.000 description 3
- 206010037888 Rash pustular Diseases 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000221577 Uromyces appendiculatus Species 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 208000029561 pustule Diseases 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- KMLMPALZGFTQQN-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-2-ethoxy-3-imidazol-1-ylpropanenitrile Chemical compound C(C)OC(C#N)(CN1C=NC=C1)C1=CC(=C(C=C1)Cl)Cl KMLMPALZGFTQQN-UHFFFAOYSA-N 0.000 description 2
- GMMHWGXHKPJLPQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-hexoxy-3-imidazol-1-ylpropanenitrile Chemical compound ClC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCCCCC GMMHWGXHKPJLPQ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- JACPTQMMZGZAOL-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCN(C)CCS(O)(=O)=O JACPTQMMZGZAOL-KHPPLWFESA-N 0.000 description 2
- HKKOPCZNFGRXTO-UHFFFAOYSA-N 2-butoxy-2-(2-fluorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=C(C=CC=C1)F HKKOPCZNFGRXTO-UHFFFAOYSA-N 0.000 description 2
- NRIJWAUUOUMNBZ-UHFFFAOYSA-N 2-butoxy-2-(4-fluorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=CC=C(C=C1)F NRIJWAUUOUMNBZ-UHFFFAOYSA-N 0.000 description 2
- KUPXRSAIVHGYGP-UHFFFAOYSA-N 2-butoxy-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=CC=CC=C1 KUPXRSAIVHGYGP-UHFFFAOYSA-N 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- PWTAMGSKOXKQBF-UHFFFAOYSA-N 2-ethoxy-2-(2-fluorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(C)OC(C#N)(CN1C=NC=C1)C1=C(C=CC=C1)F PWTAMGSKOXKQBF-UHFFFAOYSA-N 0.000 description 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- PASLUIUEENOAIW-UHFFFAOYSA-N 3-hydroxy-2-phenyl-2-propoxypropanenitrile Chemical compound OCC(C#N)(OCCC)C1=CC=CC=C1 PASLUIUEENOAIW-UHFFFAOYSA-N 0.000 description 2
- AQINEKJAVBYLAE-UHFFFAOYSA-N 3-imidazol-1-yl-2-(2-methoxyethoxy)-2-phenylpropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(C1=CC=CC=C1)OCCOC AQINEKJAVBYLAE-UHFFFAOYSA-N 0.000 description 2
- DJJWLXYNSBDQST-UHFFFAOYSA-N 3-imidazol-1-yl-2-methoxy-2-phenylpropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(C1=CC=CC=C1)OC DJJWLXYNSBDQST-UHFFFAOYSA-N 0.000 description 2
- LQULPJYCKAPLGK-UHFFFAOYSA-N 3-imidazol-1-yl-2-phenyl-2-propoxypropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(OCCC)C1=CC=CC=C1 LQULPJYCKAPLGK-UHFFFAOYSA-N 0.000 description 2
- XAUYCJPQUIHMHH-UHFFFAOYSA-N 3-methylsulfonyl-2-phenyl-2-propoxypropanenitrile Chemical compound CS(=O)(=O)CC(C#N)(OCCC)C1=CC=CC=C1 XAUYCJPQUIHMHH-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 240000004244 Cucurbita moschata Species 0.000 description 2
- 241000371644 Curvularia ravenelii Species 0.000 description 2
- OQOULEWDDRNBSG-UHFFFAOYSA-N Fenapanil Chemical compound C=1C=CC=CC=1C(CCCC)(C#N)CN1C=CN=C1 OQOULEWDDRNBSG-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
- 150000007962 benzene acetonitriles Chemical class 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
- 239000002734 clay mineral Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000005764 inhibitory process 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 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 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- NRLBEURZDFMYRZ-UHFFFAOYSA-N 2-(2,2-dimethylpropoxy)-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound CC(COC(C#N)(CN1C=NC=C1)C1=CC=CC=C1)(C)C NRLBEURZDFMYRZ-UHFFFAOYSA-N 0.000 description 1
- CUPDXNVZLUHLPG-UHFFFAOYSA-N 2-(2-chlorophenyl)-3-imidazol-1-yl-2-propoxypropanenitrile Chemical compound ClC1=C(C=CC=C1)C(C#N)(CN1C=NC=C1)OCCC CUPDXNVZLUHLPG-UHFFFAOYSA-N 0.000 description 1
- IVECYRYHGLZMOS-UHFFFAOYSA-N 2-(2-methylphenyl)propanenitrile Chemical compound N#CC(C)C1=CC=CC=C1C IVECYRYHGLZMOS-UHFFFAOYSA-N 0.000 description 1
- WOORJRTUBDSICD-UHFFFAOYSA-N 2-(3,3-dimethylbutan-2-yloxy)-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(OC(C(C)(C)C)C)C1=CC=CC=C1 WOORJRTUBDSICD-UHFFFAOYSA-N 0.000 description 1
- QQNHCZIGWBBLQL-UHFFFAOYSA-N 2-(3,3-dimethylbutoxy)-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound CC(CCOC(C#N)(CN1C=NC=C1)C1=CC=CC=C1)(C)C QQNHCZIGWBBLQL-UHFFFAOYSA-N 0.000 description 1
- JESFENYHIFEEKY-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-3-imidazol-1-yl-2-propoxypropanenitrile Chemical compound ClC=1C=C(C=CC1Cl)C(C#N)(CN1C=NC=C1)OCCC JESFENYHIFEEKY-UHFFFAOYSA-N 0.000 description 1
- FCXNKACBCFFDIL-UHFFFAOYSA-N 2-(4-bromophenyl)-2-butoxy-3-imidazol-1-ylpropanenitrile Chemical compound BrC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCCC FCXNKACBCFFDIL-UHFFFAOYSA-N 0.000 description 1
- GCMYUCTWVNAZEQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-imidazol-1-yl-2-propoxypropanenitrile Chemical compound FC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCC GCMYUCTWVNAZEQ-UHFFFAOYSA-N 0.000 description 1
- MUZYAEDDOSKNRG-UHFFFAOYSA-N 2-(4-methoxyphenyl)propanenitrile Chemical compound COC1=CC=C(C(C)C#N)C=C1 MUZYAEDDOSKNRG-UHFFFAOYSA-N 0.000 description 1
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- SXXFKLQXHTWSLT-UHFFFAOYSA-N 2-butoxy-2-(2,4-dichlorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(CCC)OC(C#N)(CN1C=NC=C1)C1=C(C=C(C=C1)Cl)Cl SXXFKLQXHTWSLT-UHFFFAOYSA-N 0.000 description 1
- GARTXNUPFOHZNK-UHFFFAOYSA-N 2-ethoxy-2-(4-fluorophenyl)-3-imidazol-1-ylpropanenitrile Chemical compound C(C)OC(C#N)(CN1C=NC=C1)C1=CC=C(C=C1)F GARTXNUPFOHZNK-UHFFFAOYSA-N 0.000 description 1
- IHPVXFFLLSNOFY-UHFFFAOYSA-N 2-ethoxy-3-imidazol-1-yl-2-phenylpropanenitrile Chemical compound C(C)OC(C#N)(CN1C=NC=C1)C1=CC=CC=C1 IHPVXFFLLSNOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- MEQQPXJGLGZGFL-UHFFFAOYSA-N 2-hexoxy-3-imidazol-1-yl-2-(2-methylphenyl)propanenitrile Chemical compound C(CCCCC)OC(C#N)(CN1C=NC=C1)C1=C(C=CC=C1)C MEQQPXJGLGZGFL-UHFFFAOYSA-N 0.000 description 1
- QIOHZPARJQADHX-UHFFFAOYSA-N 2-imidazol-1-ylpropanenitrile Chemical compound N#CC(C)N1C=CN=C1 QIOHZPARJQADHX-UHFFFAOYSA-N 0.000 description 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- NIWLGQZOKFGXID-UHFFFAOYSA-N 2-phenyl-2-propoxyacetonitrile Chemical compound C(CC)OC(C#N)C1=CC=CC=C1 NIWLGQZOKFGXID-UHFFFAOYSA-N 0.000 description 1
- NVAOLENBKNECGF-UHFFFAOYSA-N 2-phenylpropanenitrile Chemical compound N#CC(C)C1=CC=CC=C1 NVAOLENBKNECGF-UHFFFAOYSA-N 0.000 description 1
- 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- DFEVRVBTBYAOFJ-UHFFFAOYSA-N 3-imidazol-1-yl-2-(2-methylphenyl)-2-propoxypropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(OCCC)C1=C(C=CC=C1)C DFEVRVBTBYAOFJ-UHFFFAOYSA-N 0.000 description 1
- OICMABPKVBEMCE-UHFFFAOYSA-N 3-imidazol-1-yl-2-octoxy-2-phenylpropanenitrile Chemical compound N1(C=NC=C1)CC(C#N)(C1=CC=CC=C1)OCCCCCCCC OICMABPKVBEMCE-UHFFFAOYSA-N 0.000 description 1
- ADCFACIQWKPUIX-UHFFFAOYSA-N 3-imidazol-1-yl-2-phenyl-2-phenylmethoxypropanenitrile Chemical compound C(C1=CC=CC=C1)OC(C#N)(CN1C=NC=C1)C1=CC=CC=C1 ADCFACIQWKPUIX-UHFFFAOYSA-N 0.000 description 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 241000530549 Cercospora beticola Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 229920004449 Halon® Polymers 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
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241000498271 Necator Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001123559 Puccinia hordei Species 0.000 description 1
- 241001123583 Puccinia striiformis Species 0.000 description 1
- 241000228453 Pyrenophora Species 0.000 description 1
- 241000228454 Pyrenophora graminea Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- CKXBUYDKKBVDHS-UHFFFAOYSA-N [N+](=O)(O)[O-].BrC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCCC Chemical compound [N+](=O)(O)[O-].BrC1=CC=C(C=C1)C(C#N)(CN1C=NC=C1)OCCCC CKXBUYDKKBVDHS-UHFFFAOYSA-N 0.000 description 1
- KQFHMFHTWNESSI-UHFFFAOYSA-N [N+](=O)(O)[O-].C(CCCCCCCCC)OC(C#N)(CN1C=NC=C1)C1=CC=CC=C1 Chemical compound [N+](=O)(O)[O-].C(CCCCCCCCC)OC(C#N)(CN1C=NC=C1)C1=CC=CC=C1 KQFHMFHTWNESSI-UHFFFAOYSA-N 0.000 description 1
- DTRRMTXOGLGUMU-UHFFFAOYSA-N [N+](=O)(O)[O-].ClC=1C=C(C=CC1Cl)C(C#N)(CN1C=NC=C1)OCCC Chemical compound [N+](=O)(O)[O-].ClC=1C=C(C=CC1Cl)C(C#N)(CN1C=NC=C1)OCCC DTRRMTXOGLGUMU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- CKSCFUVWUMLXTP-UHFFFAOYSA-N ethyl(methoxy)mercury Chemical compound CC[Hg]OC CKSCFUVWUMLXTP-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000019674 grape juice Nutrition 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 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
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- NLSKERUUJZQBRI-UHFFFAOYSA-N triazole-1-carbaldehyde Chemical compound O=CN1C=CN=N1 NLSKERUUJZQBRI-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19813125780 DE3125780A1 (de) | 1981-06-30 | 1981-06-30 | Imidazolyl-propionitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
Publications (1)
Publication Number | Publication Date |
---|---|
CH655311A5 true CH655311A5 (de) | 1986-04-15 |
Family
ID=6135760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH3960/82A CH655311A5 (de) | 1981-06-30 | 1982-06-28 | Imidazolyl-propionitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel und mittel mit wachstumsregulierender wirkung. |
Country Status (37)
Country | Link |
---|---|
JP (1) | JPS6055070B2 (ru) |
KR (1) | KR840000506A (ru) |
AR (1) | AR231440A1 (ru) |
AT (1) | ATA247082A (ru) |
AU (1) | AU8546482A (ru) |
BE (1) | BE893696A (ru) |
BG (1) | BG37373A3 (ru) |
BR (1) | BR8203803A (ru) |
CA (1) | CA1186317A (ru) |
CH (1) | CH655311A5 (ru) |
CS (1) | CS236480B2 (ru) |
DD (1) | DD202977A5 (ru) |
DE (1) | DE3125780A1 (ru) |
DK (1) | DK291582A (ru) |
ES (1) | ES512949A0 (ru) |
FI (1) | FI822033L (ru) |
FR (1) | FR2519635A1 (ru) |
GB (1) | GB2101995B (ru) |
GR (1) | GR81396B (ru) |
HU (1) | HU189598B (ru) |
IL (1) | IL66164A (ru) |
IT (1) | IT1151802B (ru) |
LU (1) | LU84246A1 (ru) |
MA (1) | MA19512A1 (ru) |
NL (1) | NL8202339A (ru) |
NO (1) | NO822231L (ru) |
NZ (1) | NZ200967A (ru) |
PH (1) | PH19047A (ru) |
PL (1) | PL129716B1 (ru) |
PT (1) | PT75147B (ru) |
RO (1) | RO85277B (ru) |
SE (1) | SE8204027L (ru) |
SU (2) | SU1114334A3 (ru) |
TR (1) | TR21402A (ru) |
YU (1) | YU125882A (ru) |
ZA (1) | ZA824688B (ru) |
ZW (1) | ZW13182A1 (ru) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3329213A1 (de) * | 1983-08-10 | 1985-02-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | Azolyl-propannitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
DE3644616A1 (de) * | 1986-12-29 | 1988-07-07 | Lentia Gmbh | Imidazolderivate, verfahren zur herstellung und deren verwendung |
JPS63120362U (ru) * | 1987-01-28 | 1988-08-04 | ||
JPH0624355U (ja) * | 1991-07-12 | 1994-03-29 | 株式会社三輝産業 | バッテリーチャージャ |
USD872768S1 (en) | 2016-02-19 | 2020-01-14 | Sony Corporation | Robot having display screen with animated graphical user interface |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4167576A (en) * | 1977-10-06 | 1979-09-11 | Rohm And Haas Company | Cyanoaralkylheterocyclic compounds |
EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal triazole and imidazole compounds |
-
1981
- 1981-06-30 DE DE19813125780 patent/DE3125780A1/de not_active Withdrawn
-
1982
- 1982-05-14 PH PH27307A patent/PH19047A/en unknown
- 1982-06-08 FI FI822033A patent/FI822033L/fi not_active Application Discontinuation
- 1982-06-09 NL NL8202339A patent/NL8202339A/xx not_active Application Discontinuation
- 1982-06-09 ES ES512949A patent/ES512949A0/es active Granted
- 1982-06-10 YU YU01258/82A patent/YU125882A/xx unknown
- 1982-06-10 CS CS824318A patent/CS236480B2/cs unknown
- 1982-06-15 NZ NZ200967A patent/NZ200967A/en unknown
- 1982-06-18 IT IT21939/82A patent/IT1151802B/it active
- 1982-06-18 RO RO107928A patent/RO85277B/ro unknown
- 1982-06-22 JP JP57106257A patent/JPS6055070B2/ja not_active Expired
- 1982-06-24 MA MA19719A patent/MA19512A1/fr unknown
- 1982-06-24 BG BG057133A patent/BG37373A3/xx unknown
- 1982-06-25 AT AT0247082A patent/ATA247082A/de not_active Application Discontinuation
- 1982-06-25 SU SU823456111A patent/SU1114334A3/ru active
- 1982-06-25 SU SU823456292A patent/SU1245251A3/ru active
- 1982-06-28 CH CH3960/82A patent/CH655311A5/de not_active IP Right Cessation
- 1982-06-28 GR GR68583A patent/GR81396B/el unknown
- 1982-06-28 TR TR21402A patent/TR21402A/xx unknown
- 1982-06-28 FR FR8211287A patent/FR2519635A1/fr active Granted
- 1982-06-28 PL PL1982237145A patent/PL129716B1/pl unknown
- 1982-06-29 GB GB08218796A patent/GB2101995B/en not_active Expired
- 1982-06-29 DK DK291582A patent/DK291582A/da not_active Application Discontinuation
- 1982-06-29 CA CA000406258A patent/CA1186317A/en not_active Expired
- 1982-06-29 BE BE0/208488A patent/BE893696A/fr not_active IP Right Cessation
- 1982-06-29 IL IL66164A patent/IL66164A/xx unknown
- 1982-06-29 PT PT75147A patent/PT75147B/pt unknown
- 1982-06-29 BR BR8203803A patent/BR8203803A/pt unknown
- 1982-06-29 NO NO822231A patent/NO822231L/no unknown
- 1982-06-29 SE SE8204027A patent/SE8204027L/xx not_active Application Discontinuation
- 1982-06-29 HU HU822103A patent/HU189598B/hu unknown
- 1982-06-30 LU LU84246A patent/LU84246A1/de unknown
- 1982-06-30 DD DD82241259A patent/DD202977A5/de unknown
- 1982-06-30 ZW ZW131/82A patent/ZW13182A1/xx unknown
- 1982-06-30 ZA ZA824688A patent/ZA824688B/xx unknown
- 1982-06-30 AR AR289853A patent/AR231440A1/es active
- 1982-06-30 KR KR1019820002943A patent/KR840000506A/ko unknown
- 1982-06-30 AU AU85464/82A patent/AU8546482A/en not_active Abandoned
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE3406993C2 (ru) | ||
DE2635663C2 (ru) | ||
DE3234624C2 (ru) | ||
DE3614060A1 (de) | Pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
DE2547954C2 (ru) | ||
CH655311A5 (de) | Imidazolyl-propionitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel und mittel mit wachstumsregulierender wirkung. | |
DE2335020A1 (de) | 1-aethyl-triazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
EP0131793A2 (de) | 5-Aminomethyl-1,3-oxathiolane | |
EP0005754B1 (de) | Mittel und Verfahren zur Regulierung des Pflanzenwachstums | |
US4517367A (en) | Azolyl-pentene derivatives and biocidal compositions containing the same | |
CH653024A5 (de) | 1,2,4-triazol-1-yl-propionitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel. | |
DE2128700C2 (de) | Fungitoxische Mittel | |
DE3145846A1 (de) | Cycloalkyl-((alpha)-triazolyl-ss-hydroxy)-ketone, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren | |
EP0069244A1 (de) | Verfahren zur Beeinflussung des Pflanzenwachstums | |
EP0132771A2 (de) | Neue 1,2 Diaryl-3-azolyl-propan-Derivate, ihre Herstellung und Verwendung als Pflanzenbehandlungsmittel | |
DE3229734A1 (de) | Fungizide mittel | |
EP0134515A1 (de) | Azolyl-Propannitrile, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende biozide Mittel | |
DE3417264A1 (de) | Neue 2,4-diamino-6-halogen-5-alkylthio-pyrimidine | |
DE3333449A1 (de) | Fungizide mittel | |
DE2920375A1 (de) | Fungizide mittel, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide | |
DD228159A5 (de) | E-triazolyl-pentenole enthaltende biozide und wuchsregulatorische mittel | |
DE3313941A1 (de) | 4-azolyl-pentannitrile, verfahren zur herstellung dieser verbundungen sowie diese enthaltende biozide mittel | |
DE4038811A1 (de) | Neue triazole mit den pflanzenwuchs regulierender und hemmender wirkung | |
DE1966473B2 (de) | 2-cyanoalkyl-4-alkyl-1,2,4-triazolin- 3-thione und deren verwendung | |
EP0407877A2 (de) | 1,2-Dihalogenazolylethanderivate und diese enthaltende Pflanzenschutzmittel |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased | ||
PL | Patent ceased |