DD229583A5 - Fungizides mittel - Google Patents
Fungizides mittel Download PDFInfo
- Publication number
- DD229583A5 DD229583A5 DD85274119A DD27411985A DD229583A5 DD 229583 A5 DD229583 A5 DD 229583A5 DD 85274119 A DD85274119 A DD 85274119A DD 27411985 A DD27411985 A DD 27411985A DD 229583 A5 DD229583 A5 DD 229583A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- optionally substituted
- group
- pyridinyl
- active ingredient
- carbon atoms
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title description 7
- 239000004480 active ingredient Substances 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 235000013339 cereals Nutrition 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 208000031888 Mycoses Diseases 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 6
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 239000003429 antifungal agent Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 47
- 235000019198 oils Nutrition 0.000 description 46
- -1 methoxy, methylthio, ethoxy, isopropoxy Chemical group 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 16
- 239000000843 powder Substances 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 12
- 241000233866 Fungi Species 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 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 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 235000019993 champagne Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241001668536 Oculimacula yallundae Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 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 3
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 241000380131 Ammophila arenaria Species 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- 241001465180 Botrytis 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
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003415 peat Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000004550 soluble concentrate Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 150000007944 thiolates Chemical class 0.000 description 2
- 239000013008 thixotropic agent Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- OHNMTRSLNGAHKO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)sulfanyl-3,3-dimethyl-2-pyridin-3-ylbutan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)(C)C)CSC1=CC=C(Cl)C=C1Cl OHNMTRSLNGAHKO-UHFFFAOYSA-N 0.000 description 1
- VVCFLLJBHSEQRM-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)sulfanyl-3,3-dimethyl-2-pyridin-3-ylbutan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)(C)C)CSC1=CC(Cl)=CC(Cl)=C1 VVCFLLJBHSEQRM-UHFFFAOYSA-N 0.000 description 1
- ABMCGDFMCJHOTQ-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-bromophenyl)sulfanyl-1-pyridin-3-ylethanol Chemical compound C=1C=C(Br)C=CC=1C(C=1C=NC=CC=1)(O)CSC1=CC=C(Br)C=C1 ABMCGDFMCJHOTQ-UHFFFAOYSA-N 0.000 description 1
- VVLDFMANGSESJF-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-chlorophenyl)sulfanyl-1-pyridin-3-ylethanol Chemical compound C=1C=C(Br)C=CC=1C(C=1C=NC=CC=1)(O)CSC1=CC=C(Cl)C=C1 VVLDFMANGSESJF-UHFFFAOYSA-N 0.000 description 1
- UDRNZGKZBDNPJC-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(4-methylphenyl)sulfanyl-1-pyridin-3-ylethanol Chemical compound C1=CC(C)=CC=C1SCC(O)(C=1C=NC=CC=1)C1=CC=C(Br)C=C1 UDRNZGKZBDNPJC-UHFFFAOYSA-N 0.000 description 1
- QCKCUQBGAUDICB-UHFFFAOYSA-N 1-(4-bromophenyl)sulfanyl-2-pyridin-3-ylpropan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C)CSC1=CC=C(Br)C=C1 QCKCUQBGAUDICB-UHFFFAOYSA-N 0.000 description 1
- DEGZOZFSJLCCJL-UHFFFAOYSA-N 1-(4-bromophenyl)sulfanyl-3,3-dimethyl-2-pyridin-3-ylpentan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)(C)CC)CSC1=CC=C(Br)C=C1 DEGZOZFSJLCCJL-UHFFFAOYSA-N 0.000 description 1
- ZOFQVOBZHVCZGB-UHFFFAOYSA-N 1-(4-bromophenyl)sulfanyl-3-methyl-2-pyridin-3-ylbutan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)C)CSC1=CC=C(Br)C=C1 ZOFQVOBZHVCZGB-UHFFFAOYSA-N 0.000 description 1
- ZSWIQUYMXXVHQG-UHFFFAOYSA-N 1-(4-bromophenyl)sulfanyl-3-methyl-2-pyridin-3-ylnonan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)CCCCCC)CSC1=CC=C(Br)C=C1 ZSWIQUYMXXVHQG-UHFFFAOYSA-N 0.000 description 1
- AXCFLXXRXRHSSG-UHFFFAOYSA-N 1-(4-bromophenyl)sulfanyl-3-methyl-2-pyridin-3-ylpentan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)CC)CSC1=CC=C(Br)C=C1 AXCFLXXRXRHSSG-UHFFFAOYSA-N 0.000 description 1
- ROAAKYJGBPWBRA-UHFFFAOYSA-N 1-(4-bromophenyl)sulfanyl-4-methyl-2-pyridin-3-ylpentan-2-ol Chemical compound C=1C=CN=CC=1C(O)(CC(C)C)CSC1=CC=C(Br)C=C1 ROAAKYJGBPWBRA-UHFFFAOYSA-N 0.000 description 1
- CLHRZWRLSUKMDT-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-chlorophenyl)sulfanyl-1-pyridin-3-ylethanol Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=NC=CC=1)(O)CSC1=CC=C(Cl)C=C1 CLHRZWRLSUKMDT-UHFFFAOYSA-N 0.000 description 1
- AWKYGUPHDZEOHC-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(4-methylphenyl)sulfanyl-1-pyridin-3-ylethanol Chemical compound C1=CC(C)=CC=C1SCC(O)(C=1C=NC=CC=1)C1=CC=C(Cl)C=C1 AWKYGUPHDZEOHC-UHFFFAOYSA-N 0.000 description 1
- AUPMMSGYYIVGRT-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-naphthalen-2-ylsulfanyl-1-pyridin-3-ylethanol Chemical compound C=1C=C2C=CC=CC2=CC=1SCC(O)(C=1C=NC=CC=1)C1=CC=C(Cl)C=C1 AUPMMSGYYIVGRT-UHFFFAOYSA-N 0.000 description 1
- PWVSNPWLWGNICY-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfanyl-2-pyridin-3-ylpropan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C)CSC1=CC=C(Cl)C=C1 PWVSNPWLWGNICY-UHFFFAOYSA-N 0.000 description 1
- JOIWTRJIGYROND-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfanyl-3,3-dimethyl-2-pyridin-3-ylbutan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)(C)C)CSC1=CC=C(Cl)C=C1 JOIWTRJIGYROND-UHFFFAOYSA-N 0.000 description 1
- MPJMSSSYBUARQS-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfanyl-3-methyl-2-pyridin-3-ylhexan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)CCC)CSC1=CC=C(Cl)C=C1 MPJMSSSYBUARQS-UHFFFAOYSA-N 0.000 description 1
- SQXDFDILWWQETN-UHFFFAOYSA-N 1-(4-dodecylphenyl)sulfanyl-3,3-dimethyl-2-pyridin-3-ylbutan-2-ol Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1SCC(O)(C(C)(C)C)C1=CC=CN=C1 SQXDFDILWWQETN-UHFFFAOYSA-N 0.000 description 1
- OIUJZZJVEHGZPX-UHFFFAOYSA-N 1-(4-dodecylphenyl)sulfanyl-3,3-dimethyl-2-pyridin-3-ylpentan-2-ol Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1SCC(O)(C(C)(C)CC)C1=CC=CN=C1 OIUJZZJVEHGZPX-UHFFFAOYSA-N 0.000 description 1
- ZSZVFDZNSXURTC-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfanyl-3,3-dimethyl-2-pyridin-3-ylpentan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)(C)CC)CSC1=CC=C(F)C=C1 ZSZVFDZNSXURTC-UHFFFAOYSA-N 0.000 description 1
- BXQARKQKXJVEML-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfanyl-3,3-dimethyl-2-pyridin-3-ylpentan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)(C)CC)CSC1=CC=C(OC)C=C1 BXQARKQKXJVEML-UHFFFAOYSA-N 0.000 description 1
- GKYIQGKFIORTJQ-UHFFFAOYSA-N 1-(4-methylphenyl)sulfanyl-2-pyridin-3-ylpropan-2-ol Chemical compound C1=CC(C)=CC=C1SCC(C)(O)C1=CC=CN=C1 GKYIQGKFIORTJQ-UHFFFAOYSA-N 0.000 description 1
- JWYMUJLLJLYBGO-UHFFFAOYSA-N 1-naphthalen-2-ylsulfanyl-2-pyridin-3-ylpropan-2-ol Chemical compound C=1C=C2C=CC=CC2=CC=1SCC(O)(C)C1=CC=CN=C1 JWYMUJLLJLYBGO-UHFFFAOYSA-N 0.000 description 1
- ZSJLVOHJQKDOTD-UHFFFAOYSA-N 1-phenyl-1-pyridin-3-yl-2-[4-(trifluoromethyl)phenyl]sulfanylethanol Chemical compound C=1C=CC=CC=1C(C=1C=NC=CC=1)(O)CSC1=CC=C(C(F)(F)F)C=C1 ZSJLVOHJQKDOTD-UHFFFAOYSA-N 0.000 description 1
- RTWSBBZKUXEHRT-UHFFFAOYSA-N 2-(4-bromophenyl)sulfanyl-1-(4-chlorophenyl)-1-pyridin-3-ylethanol Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=NC=CC=1)(O)CSC1=CC=C(Br)C=C1 RTWSBBZKUXEHRT-UHFFFAOYSA-N 0.000 description 1
- PHELWNOEVCGJAI-UHFFFAOYSA-N 2-(4-bromophenyl)sulfanyl-1-phenyl-1-pyridin-3-ylethanol Chemical compound C=1C=CC=CC=1C(C=1C=NC=CC=1)(O)CSC1=CC=C(Br)C=C1 PHELWNOEVCGJAI-UHFFFAOYSA-N 0.000 description 1
- ABQMQWZYBCLRMP-UHFFFAOYSA-N 2-(4-bromophenyl)sulfanyl-1-pyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(O)CSC1=CC=C(Br)C=C1 ABQMQWZYBCLRMP-UHFFFAOYSA-N 0.000 description 1
- XOVGJNPVIHGHPQ-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-1-pyridin-3-ylethanol Chemical compound C=1C=CN=CC=1C(O)CSC1=CC=C(Cl)C=C1 XOVGJNPVIHGHPQ-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 1
- FOWKOOAHJFESOM-UHFFFAOYSA-N 2-naphthalen-2-ylsulfanyl-1-phenyl-1-pyridin-3-ylethanol Chemical compound C=1C=C2C=CC=CC2=CC=1SCC(O)(C=1C=NC=CC=1)C1=CC=CC=C1 FOWKOOAHJFESOM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- KANSLNVTKOJTAH-UHFFFAOYSA-N 3,3-dimethyl-1-(4-methylphenyl)sulfanyl-2-pyridin-3-ylbutan-2-ol Chemical compound C1=CC(C)=CC=C1SCC(O)(C(C)(C)C)C1=CC=CN=C1 KANSLNVTKOJTAH-UHFFFAOYSA-N 0.000 description 1
- FJMQSSXMSJJXQP-UHFFFAOYSA-N 3,3-dimethyl-1-(4-methylphenyl)sulfanyl-2-pyridin-3-ylpentan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)(C)CC)CSC1=CC=C(C)C=C1 FJMQSSXMSJJXQP-UHFFFAOYSA-N 0.000 description 1
- GRKKLMGNXSXEIO-UHFFFAOYSA-N 3,3-dimethyl-1-(4-nonylphenyl)sulfanyl-2-pyridin-3-ylbutan-2-ol Chemical compound C1=CC(CCCCCCCCC)=CC=C1SCC(O)(C(C)(C)C)C1=CC=CN=C1 GRKKLMGNXSXEIO-UHFFFAOYSA-N 0.000 description 1
- OFJDNABPZBYGCB-UHFFFAOYSA-N 3,3-dimethyl-1-(4-nonylphenyl)sulfanyl-2-pyridin-3-ylpentan-2-ol Chemical compound C1=CC(CCCCCCCCC)=CC=C1SCC(O)(C(C)(C)CC)C1=CC=CN=C1 OFJDNABPZBYGCB-UHFFFAOYSA-N 0.000 description 1
- OURWILZWXVDTTM-UHFFFAOYSA-N 3-methyl-1-(4-nonylphenyl)sulfanyl-2-pyridin-3-ylpentan-2-ol Chemical compound C1=CC(CCCCCCCCC)=CC=C1SCC(O)(C(C)CC)C1=CC=CN=C1 OURWILZWXVDTTM-UHFFFAOYSA-N 0.000 description 1
- OVRYWDJUDYHSLA-UHFFFAOYSA-N 3-methyl-2-pyridin-3-yl-1-(2,4,5-trichlorophenyl)sulfanylpentan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)CC)CSC1=CC(Cl)=C(Cl)C=C1Cl OVRYWDJUDYHSLA-UHFFFAOYSA-N 0.000 description 1
- MQSQDOITFVJATE-UHFFFAOYSA-N 3-methyl-2-pyridin-3-yl-1-[4-(trifluoromethyl)phenyl]sulfanylbutan-2-ol Chemical compound C=1C=CN=CC=1C(O)(C(C)C)CSC1=CC=C(C(F)(F)F)C=C1 MQSQDOITFVJATE-UHFFFAOYSA-N 0.000 description 1
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- 241001290235 Ceratobasidium cereale Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
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- 241000223194 Fusarium culmorum Species 0.000 description 1
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- 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
- 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
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- 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
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- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 244000082988 Secale cereale Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
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- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
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- 125000000129 anionic group Chemical group 0.000 description 1
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- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- 239000000084 colloidal system Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
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- 238000005469 granulation Methods 0.000 description 1
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- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
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- 238000000265 homogenisation Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 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
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000037921 secondary disease Diseases 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 150000004760 silicates 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- VZGYROLJKOBEOF-UHFFFAOYSA-M sodium;4-methylthiophene-2-carboxylate Chemical compound [Na+].CC1=CSC(C([O-])=O)=C1 VZGYROLJKOBEOF-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8404235A FR2561239B1 (fr) | 1984-03-15 | 1984-03-15 | Arylthio-pyridinyl-alcanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD229583A5 true DD229583A5 (de) | 1985-11-13 |
Family
ID=9302193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85274119A DD229583A5 (de) | 1984-03-15 | 1985-03-14 | Fungizides mittel |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4677128A (en, 2012) |
| EP (1) | EP0157712A1 (en, 2012) |
| JP (1) | JPS60222459A (en, 2012) |
| KR (1) | KR850006176A (en, 2012) |
| AU (1) | AU3984685A (en, 2012) |
| BR (1) | BR8501138A (en, 2012) |
| CA (1) | CA1244832A (en, 2012) |
| DD (1) | DD229583A5 (en, 2012) |
| DK (1) | DK117385A (en, 2012) |
| ES (1) | ES8607935A1 (en, 2012) |
| FR (1) | FR2561239B1 (en, 2012) |
| GR (1) | GR850636B (en, 2012) |
| HU (1) | HUT37599A (en, 2012) |
| IL (1) | IL74578A (en, 2012) |
| PT (1) | PT80111B (en, 2012) |
| ZA (1) | ZA851936B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3815700A1 (de) * | 1987-08-05 | 1989-02-16 | Bayer Ag | Substituierte pyridyl(3)-alkanole, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| GB8814639D0 (en) * | 1988-06-20 | 1988-07-27 | Ici Plc | Heterocyclic tertiary alcohol derivatives |
| FR2634199B1 (fr) * | 1988-07-13 | 1990-09-14 | Rhone Poulenc Agrochimie | Composes herbicides et les compositions les contenant |
| FR2645536B1 (fr) * | 1989-04-10 | 1991-05-31 | Rhone Poulenc Agrochimie | Composes herbicides et les compositions les contenant |
| FR2656612B1 (fr) * | 1989-12-28 | 1992-03-27 | Rhone Poulenc Agrochimie | Herbicides a groupe alcenyle ou heteroaryle thio, sulfone, sulfoxyde. |
| DE4229643A1 (de) * | 1992-09-04 | 1994-03-10 | Bayer Ag | Substituierte Hydroxyalkylpyridine |
| WO2011003527A1 (de) * | 2009-07-08 | 2011-01-13 | Bayer Cropscience Ag | Phenyl(oxy/thio)alkanol-derivate |
| EA019612B1 (ru) * | 2009-07-08 | 2014-04-30 | Байер Кропсайенс Аг | Замещенные производные фенил(окси/тио)алканолов |
| MX2013005948A (es) | 2010-11-30 | 2013-07-03 | Bayer Ip Gmbh | Derivados de pirimidina. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3849423A (en) * | 1971-03-22 | 1974-11-19 | Lilly Co Eli | 3-benzylpyridines |
| US3869456A (en) * | 1972-03-13 | 1975-03-04 | Lilly Co Eli | Synthesis of 5-pyrimidinecarbinols |
| DE2742173A1 (de) * | 1977-09-20 | 1979-03-29 | Bayer Ag | Phenoxy-pyridinyl(pyrimidinyl)-alkanole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| AU554104B2 (en) * | 1981-09-01 | 1986-08-07 | F. Hoffmann-La Roche Ag | Heterocyclic compounds and fungicides containing same |
-
1984
- 1984-03-15 FR FR8404235A patent/FR2561239B1/fr not_active Expired
-
1985
- 1985-02-26 US US06/705,558 patent/US4677128A/en not_active Expired - Fee Related
- 1985-03-05 ES ES540924A patent/ES8607935A1/es not_active Expired
- 1985-03-12 IL IL74578A patent/IL74578A/xx unknown
- 1985-03-13 GR GR850636A patent/GR850636B/el unknown
- 1985-03-13 JP JP60050244A patent/JPS60222459A/ja active Pending
- 1985-03-13 EP EP85420046A patent/EP0157712A1/fr not_active Withdrawn
- 1985-03-14 DK DK117385A patent/DK117385A/da not_active Application Discontinuation
- 1985-03-14 PT PT80111A patent/PT80111B/pt unknown
- 1985-03-14 DD DD85274119A patent/DD229583A5/de unknown
- 1985-03-14 AU AU39846/85A patent/AU3984685A/en not_active Abandoned
- 1985-03-14 BR BR8501138A patent/BR8501138A/pt unknown
- 1985-03-14 ZA ZA851936A patent/ZA851936B/xx unknown
- 1985-03-14 CA CA000476513A patent/CA1244832A/en not_active Expired
- 1985-03-14 HU HU85952A patent/HUT37599A/hu unknown
- 1985-03-15 KR KR1019850001683A patent/KR850006176A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| HUT37599A (en) | 1986-01-23 |
| FR2561239B1 (fr) | 1986-09-05 |
| KR850006176A (ko) | 1985-10-02 |
| GR850636B (en, 2012) | 1985-07-09 |
| JPS60222459A (ja) | 1985-11-07 |
| IL74578A0 (en) | 1985-06-30 |
| AU3984685A (en) | 1985-10-31 |
| DK117385A (da) | 1985-09-16 |
| PT80111A (fr) | 1985-04-01 |
| US4677128A (en) | 1987-06-30 |
| ZA851936B (en) | 1985-11-27 |
| ES8607935A1 (es) | 1986-06-01 |
| IL74578A (en) | 1988-04-29 |
| ES540924A0 (es) | 1986-06-01 |
| PT80111B (fr) | 1987-03-24 |
| CA1244832A (en) | 1988-11-15 |
| FR2561239A1 (fr) | 1985-09-20 |
| DK117385D0 (da) | 1985-03-14 |
| BR8501138A (pt) | 1985-11-12 |
| EP0157712A1 (fr) | 1985-10-09 |
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