CS199531B2 - Fungicide and process for preparing effective compounds - Google Patents
Fungicide and process for preparing effective compounds Download PDFInfo
- Publication number
- CS199531B2 CS199531B2 CS783506A CS350678A CS199531B2 CS 199531 B2 CS199531 B2 CS 199531B2 CS 783506 A CS783506 A CS 783506A CS 350678 A CS350678 A CS 350678A CS 199531 B2 CS199531 B2 CS 199531B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- active
- weight
- plants
- optionally substituted
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 title description 25
- 239000000417 fungicide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 benzoylmethyl Chemical group 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- GCDVQIPVANUWJO-UHFFFAOYSA-O 1-(2-phenylethyl)-1H-triazol-1-ium Chemical class C1(=CC=CC=C1)CC[NH+]1N=NC=C1 GCDVQIPVANUWJO-UHFFFAOYSA-O 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 239000013543 active substance Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000006286 dichlorobenzyl group Chemical group 0.000 claims description 2
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 206010061217 Infestation Diseases 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 235000010633 broth Nutrition 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 241000221785 Erysiphales Species 0.000 description 7
- 241000220225 Malus Species 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 4
- WNLYOHQDXYUFCT-UHFFFAOYSA-N 1-phenyl-2-(2h-triazol-4-yl)ethanol Chemical class C=1C=CC=CC=1C(O)CC1=CNN=N1 WNLYOHQDXYUFCT-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000489964 Fusicladium Species 0.000 description 4
- 208000031888 Mycoses Diseases 0.000 description 4
- 206010039509 Scab Diseases 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000009885 systemic effect Effects 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
- 229920001817 Agar Polymers 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 206010053759 Growth retardation Diseases 0.000 description 2
- 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 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 238000002156 mixing Methods 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- XCWJBJOPHSVLGU-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)CN1C=NC=N1 XCWJBJOPHSVLGU-UHFFFAOYSA-N 0.000 description 1
- GCDVQIPVANUWJO-UHFFFAOYSA-N 1-(2-phenylethyl)triazole Chemical class C=1C=CC=CC=1CCN1C=CN=N1 GCDVQIPVANUWJO-UHFFFAOYSA-N 0.000 description 1
- IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 1
- KSPMHMMSPIMHRK-UHFFFAOYSA-N 2-methyl-1H-1,2,4-triazol-2-ium iodide Chemical compound [I-].C[N+]=1NC=NC=1 KSPMHMMSPIMHRK-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241001480061 Blumeria graminis Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000760356 Chytridiomycetes Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical group CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001503460 Plasmodiophorida Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 241000228454 Pyrenophora graminea Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000287436 Turdus merula Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 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
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772725314 DE2725314A1 (de) | 1977-06-04 | 1977-06-04 | 1-(2-phenylaethyl)-triazolium-salze, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199531B2 true CS199531B2 (en) | 1980-07-31 |
Family
ID=6010741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS783506A CS199531B2 (en) | 1977-06-04 | 1978-05-30 | Fungicide and process for preparing effective compounds |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0000017B1 (pl) |
| JP (1) | JPS543070A (pl) |
| AU (1) | AU3684878A (pl) |
| BR (1) | BR7803551A (pl) |
| CA (1) | CA1100976A (pl) |
| CS (1) | CS199531B2 (pl) |
| DD (1) | DD137658A5 (pl) |
| DE (2) | DE2725314A1 (pl) |
| DK (1) | DK248378A (pl) |
| ES (1) | ES470458A1 (pl) |
| IL (1) | IL54840A (pl) |
| IT (1) | IT7824171A0 (pl) |
| PL (1) | PL109267B1 (pl) |
| PT (1) | PT68100A (pl) |
| TR (1) | TR19791A (pl) |
| ZA (1) | ZA783176B (pl) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6224254Y2 (pl) * | 1979-09-17 | 1987-06-20 | ||
| DE2937595A1 (de) * | 1979-09-18 | 1981-04-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1-azolyl-1-phenoxy-alkan-2-onen |
| CA1179678A (en) * | 1981-03-27 | 1984-12-18 | Elmar Sturm | Antimicrobial triazole derivatives |
| GB2143815B (en) * | 1983-05-19 | 1988-01-20 | Ciba Geigy Ag | Process for the preparation of micro biocidal 1-triazolylethyl ether derivatives |
| DE3319845A1 (de) * | 1983-06-01 | 1984-12-06 | Basf Ag, 6700 Ludwigshafen | Arylalkylimidazolium- und -triazoliumsalze, verfahren zu ihrer herstellung und ihre verwendung als mikrozide |
| IT1200422B (it) * | 1985-03-19 | 1989-01-18 | Ripari Gero Ist Farm Biolog | Composto con attivita' antimicrobia,sua preparazione e composizioni farmaceutiche che lo contengono |
| DE3860278D1 (de) * | 1987-01-21 | 1990-08-09 | Ciba Geigy Ag | Mikrobizides mittel. |
| SK45795A3 (en) * | 1992-10-09 | 1995-10-11 | Uniroyal Chemical Ltd | Substituted azole derivatives as fungicidal effective matters, method of preparing of these compounds, intermediates of this method, fungicidal agent containing these derivatives and controlling method of phytogene molds |
| CA2840286C (en) | 2011-07-13 | 2016-04-12 | Basf Se | Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds |
| BR112014000538A2 (pt) | 2011-07-15 | 2016-08-23 | Basf Se | compostos, processo para a preparação dos compostos, composições agroquímicas, utilização dos compostos e semente revestida |
| PE20140837A1 (es) | 2011-07-15 | 2014-07-10 | Basf Se | Compuestos fungicidas 2-[2-cloro-4-(4-cloro-fenoxi)-fenil]-1-[1,2,4]triazol-1-il-etanol alquilo sustituidos |
| MX2014000511A (es) | 2011-08-15 | 2014-02-19 | Basf Se | Compuestos fungicidas de 1-{2-[2-halo-4-(4-halogen-fenoxi)-fenil]- 2-etoxi-etil}-1h-[1,2,4]triazol sustituidos. |
| BR112014003412A2 (pt) | 2011-08-15 | 2017-03-14 | Basf Se | compostos de fórmula i, processo, compostos de fórmula xii, viii e xi, composições agroquímicas, utilização e semente revestida |
| AU2012296893A1 (en) | 2011-08-15 | 2014-03-06 | Basf Se | Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl/alkenyl-ethyl}-1H-[1,2,4]triazole compounds |
| KR20140080482A (ko) | 2011-08-15 | 2014-06-30 | 바스프 에스이 | 살진균 치환된 1-{2-[2-할로-4-(4-할로겐-페녹시)-페닐]-2-알콕시-3-메틸-부틸}-1h-[1,2,4]트리아졸 화합물 |
| BR112015014753B8 (pt) | 2012-12-20 | 2020-03-03 | Basf Agro Bv | composições, uso de uma composição, método para o combate de fungos fitopatogênicos e uso dos componentes |
| BR122019013926B1 (pt) | 2013-01-09 | 2019-10-29 | Basf Agro Bv | processo para preparar um composto de triazol de fórmula i |
| UA118265C2 (uk) | 2013-07-08 | 2018-12-26 | Басф Агро Б.В. | Композиції, що містять триазольну сполуку і біопестицид |
| UA119672C2 (uk) | 2014-06-25 | 2019-07-25 | Басф Агро Б.В. | Пестицидні композиції |
| AU2015342067B2 (en) | 2014-11-07 | 2019-10-31 | Basf Se | Pesticidal mixtures |
| BR112018003173B1 (pt) | 2015-08-20 | 2021-12-14 | Nilever Ip Holdings B.V. | Lactama encapsulada, aditivo, composição e método de encapsulamento de uma lactama |
| JP6903074B2 (ja) | 2016-03-16 | 2021-07-14 | ビーエイエスエフ・ソシエタス・エウロパエアBasf Se | 穀類につく耐性植物病原菌類を駆除するためのテトラゾリノンの使用 |
| WO2017157916A1 (en) | 2016-03-16 | 2017-09-21 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean |
| US11425909B2 (en) | 2016-03-16 | 2022-08-30 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ181916A (en) * | 1975-09-10 | 1979-01-11 | Ici Ltd | 1-substituted-1,2,4-triazoles and fungicidal compositions |
-
1977
- 1977-06-04 DE DE19772725314 patent/DE2725314A1/de not_active Withdrawn
-
1978
- 1978-05-22 DD DD78205501A patent/DD137658A5/xx unknown
- 1978-05-29 PT PT68100A patent/PT68100A/pt unknown
- 1978-05-30 TR TR19791A patent/TR19791A/xx unknown
- 1978-05-30 CS CS783506A patent/CS199531B2/cs unknown
- 1978-06-01 DE DE7878100029T patent/DE2861233D1/de not_active Expired
- 1978-06-01 EP EP78100029A patent/EP0000017B1/de not_active Expired
- 1978-06-01 IL IL54840A patent/IL54840A/xx unknown
- 1978-06-01 JP JP6499878A patent/JPS543070A/ja active Pending
- 1978-06-02 DK DK248378A patent/DK248378A/da unknown
- 1978-06-02 PL PL1978207336A patent/PL109267B1/pl unknown
- 1978-06-02 BR BR787803551A patent/BR7803551A/pt unknown
- 1978-06-02 CA CA304,664A patent/CA1100976A/en not_active Expired
- 1978-06-02 IT IT7824171A patent/IT7824171A0/it unknown
- 1978-06-02 ES ES470458A patent/ES470458A1/es not_active Expired
- 1978-06-02 ZA ZA00783176A patent/ZA783176B/xx unknown
- 1978-06-06 AU AU36848/78A patent/AU3684878A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT68100A (de) | 1978-06-01 |
| IL54840A0 (en) | 1978-08-31 |
| IT7824171A0 (it) | 1978-06-02 |
| DE2861233D1 (en) | 1981-12-10 |
| TR19791A (tr) | 1979-12-19 |
| EP0000017A1 (de) | 1978-12-20 |
| DD137658A5 (de) | 1979-09-19 |
| JPS543070A (en) | 1979-01-11 |
| AU3684878A (en) | 1979-12-13 |
| DE2725314A1 (de) | 1978-12-14 |
| IL54840A (en) | 1982-03-31 |
| CA1100976A (en) | 1981-05-12 |
| ZA783176B (en) | 1979-06-27 |
| DK248378A (da) | 1978-12-05 |
| PL207336A1 (pl) | 1979-02-26 |
| EP0000017B1 (de) | 1981-09-30 |
| PL109267B1 (en) | 1980-05-31 |
| BR7803551A (pt) | 1979-02-20 |
| ES470458A1 (es) | 1979-01-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS199531B2 (en) | Fungicide and process for preparing effective compounds | |
| US4518600A (en) | Combating fungi with 1-phenoxy-2-pyrimidinyl alkanols | |
| CA1212952A (en) | 1-phenyl-2-triazolyl-ethyl ether derivatives and their use as fungicides | |
| US4548945A (en) | Fungicidally active substituted 1-hydroxyethyl-triazolyl derivatives | |
| US4232033A (en) | Combating fungi with diastereomeric form A of 1-phenoxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ols | |
| US4309434A (en) | Combating fungi with 1-(2-chlorophenyl)-1-(2-chlorobenzyloximino)-2-(1,2,4-triazol-1-yl)-ethane | |
| CA1092130A (en) | Azolyl-carboxylic acid derivatives and their use as fungicides | |
| CS215063B2 (en) | Fungicide means and means for suppressing the non-desirable plant growth | |
| US4251540A (en) | Combating crop damaging fungi with α-(4-biphenylyl)-benzyl-azolium salts | |
| US4366152A (en) | Combatting fungi with metal salt complexes of 1-phenyl-2-(1,2,4-triazol-1-yl)-ethanes | |
| CS195322B2 (en) | Fungicide and method of preparing active substances therefor | |
| US4472416A (en) | Combating fungi with substituted azolyl-phenoxy derivatives | |
| JPS6026111B2 (ja) | 新規な1−アゾリル−4−ヒドロキシ−ブタン誘導体,その製造方法およびそれを活性成分として含有する殺菌剤組成物 | |
| CS227695B2 (en) | Fungicide | |
| US4599348A (en) | 1-azolyl-substituted oxime ether fungicides | |
| IL45178A (en) | 1-phenoxy-1-(3(5)-halo-1,2,4-triazol-1-yl)-3,3-dimethyl-butan-2-one derivatives their preparation and their use as fungicides | |
| CA1088549A (en) | 1-acyloxy-1-phenyl-2-azolyl-ethanes, and their use as fungicides or nematocides | |
| CA1077495A (en) | Acylated imidazolyl-0, n-acetals, process for their preparation and their use as fungicides | |
| US4921870A (en) | Fungicidal novel substituted phenethyl-triazolyl derivatives | |
| CA1156659A (en) | Combating fungi with trisubstituted benzyl oxime ethers | |
| HU189687B (en) | Fungicide and growth-regulating compositions for plants containing 1-azolyl-2-oximino-butan derivatives as active agents and process for producing 1-azolyl-2-oximino-butan derivatives | |
| IE52517B1 (en) | Azolylmethyl-1,3-dioxolane and-dioxane derivatives processes for their preparation,and their use as fungicides | |
| GB1568350A (en) | Azolyl-alkane-carboxylic acid derivatives and their use as fungicides | |
| CA1213592A (en) | Substituted azolylether-ketones and -carbinols | |
| JPH064599B2 (ja) | ヒドロキシエチル‐アゾール誘導体 |