PL119636B1 - - Google Patents

Download PDF

Info

Publication number
PL119636B1
PL119636B1 PL220417A PL22041779A PL119636B1 PL 119636 B1 PL119636 B1 PL 119636B1 PL 220417 A PL220417 A PL 220417A PL 22041779 A PL22041779 A PL 22041779A PL 119636 B1 PL119636 B1 PL 119636B1
Authority
PL
Poland
Prior art keywords
chj
triazole
formula
imidazole
pyrazole
Prior art date
Application number
PL220417A
Other languages
English (en)
Other versions
PL119636B2 (en
PL220417A2 (pl
Original Assignee
Basf Aktiengesellschaft
Filing date
Publication date
Priority claimed from DE19782854598 external-priority patent/DE2854598A1/de
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of PL220417A2 publication Critical patent/PL220417A2/xx
Publication of PL119636B2 publication Critical patent/PL119636B2/xx
Publication of PL119636B1 publication Critical patent/PL119636B1/pl

Links

Classifications

    • 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
    • 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
    • C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • 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
    • 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
    • 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
    • C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/68—Halogen 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Description

* ** CH2 CH2 CH2 CH2 CH2 CH2 2,4—Cli-fenyl 2,4—Clrfenyl 2,6-dwufluorofenyl 2,6-dwufluorofenyl fenvl fenyl OCH3 wzór 27 wzór 27 furyl-2 (CH2)3 furyl-2 furyl-2 furyl-2 fenyl 2-metylofenyl Z4—Orfcnyl wzór 12 tienyl-2 tienyl-2 2,54wumetylofuryl-3 2,5-d wumetylofury 1- 3 2,6-dwuchloropirydyM 2,6-dwuchloropirydyl-4 1,2,4-triazol 4,5-dwuchloroimidazol 1,2,4-triazol imidazol imidazol 1,2,4-triazol 1,2,4-triazol 1,2,4-triazol imidazol 1,2,4-triazol pirazol imidazol 1,2,4-triazol 1,2,4-triazol 1,2,4-triazol 1,2,4-triazol 1,2,4-triazol 1,2,4-triazol . imidazol 1,2,4-triazol pirazol pirazol imidazol 1,2,4-triazol 163 120 165-167 134-135 125 130-132 58 163-164 115-116 140 66 89 104 86 104 130 108-110 141 148-149 130-131 90-91 110-111 120-122 126-127 Tablica V Nr Stale fizy- biezacy R1 R2 R3 Z R4 A czne (temp. top.°C) 389 390 391 392 393 394 396 397 398 399 401 CjH7i CHj CH3 C2H, C2H5 C2H5 CHj C2H5 C2H5 CHj C2H5 C,H7i CHj CHj C2H5 C2H5 CjHj CHj C2H, C,Hj CHj C2H5 H H H H H H H H H H H CH2 CH2 (CH2), CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 fenyl 3-NOrfcnyl —CHjOCHj wzór 28 wzór 4 wzór 4 —CHj—CH2—F 3-metyloizoksazolil-5 3-metyloizoksazolil-5 wzór 27 wzór 27 2-metylo-imidazol 2-ctylo-imidazol pirazol imidazol imidazol 1,2,4-triazol l,Z4-triazol imidazol 1,2,4-triazol 2-etyloimidazol 2-metylo-imidazol 133-135 138-139 74-76 75-77 nD22l,5983 75-76 89-91 97-98 121-122 82-83 98-100 Tablica VI Porazenie ilosci po opryskaniu ciecza Substancja zawierajaca substancje czynna w % czynna 178 179 183 189 194 196 197 199 201 204 240 244 246 0,1 1 1 1 1 1 1 1 0 0 1 0 1 1 0,05 2 2 2 2 2 2 2 1 0 2 1 2 216 119 636 250 2i6 262 276 277 298 302 304 347 373 374 A (znana) kontrola (nie trakto¬ wana) 1 0 0 u 0 1 0 0 0 1 I 2 5 0- brak porazenia, stopniowo co 5 =calkowile po¬ razenie Tablica VII Substancja czynna 189 200 201 250 256 261 270 276 316 332 365 368 395 kontrola (nie traktowana) Porazenie lisci po opryskaniu ciecza zawierajaca 0,1% substancji czynnej 2 2 2 2 0 1 0 2 0 l 0 1 1 5 0=brak porazenia, stopniowo do 5= calkowite porazenie119 636 (R3 CH-<0 CH3 WZÓR 3 V WZÓR 1 R1 Z-A < .'C-R4 II 0 <^0)-CH=CH WZÓR 4 -CK WZÓR 6 CH2 "(l) -Ch^-O -^H) wzór 7 wzór 8 -ch2-o-(h} WZÓR 9 0"CH2- -ch2-0-@ WZÓR 10 WZÓR 11119 636 a -CK ,-o^-a -c^-s-^g) -ch2-s-@-ci WZOR 12 WZÓR 16 WZOR 17 -CK {o-p a WZOR 13 C^o-^ -CH^-O-^-Cl a WZOR U WZOR 6 CK y& WZÓR 18 O-NH-Z-A R4 WZOR 20 CH3 ^-H^ \ CK, C-CH. 3 II 0 ^-" 5°SiH5 WZOR 21 _,C2H5,CH2''^ V m XCO-0 C2H5 WZOR 22 CH, CK, CH3 C-CH2-OCH3 CH3 CK C^N = C-V^J CH, WZOR 24 CH, ^3 3 A CK WZOR 25 ChU \ WZOR 23 CHo WZOR 26119 636 -o-O WZÓR 17 CH- I CH3 -O WZÓR 28 WZÓR 29 ^-N CHo CHUCI CH3 CO-0 WZÓR 30 CH3 C^-N-Of o WZÓR 31 ¦ C '/ C2H5 CH2Cl WZOR 32 CoHc ChL-NO Cl /£N €fN 2n5 w^-iy^ / a ;N CH3 CH2-N,Oj WZQR 3J CH3XC ^Q O WZOR 35 92H5 /H CL (OK7 Cl ?H5XCO^N Cl WZOR 36 C^ ChL - NO, WZOR 37119 636 CH- , CH0Ci CH3 ^ /*N CH3 CH2-N^J SCHEMAT 1 n R^-CO Hal* WZDR 2 SCHEMAT 2 N=ChL + R5-X-COHal SCHEMAT 3 N=CH • ^-^-n/ "5 ^ ?Cl-C-X-R r' ¦2 O WZDR 19 SCHEMAT 4 Pracownia Poligraficzna L'P PRL. Niklad 120 egz.Cena 100 zl PL PL PL

Claims (1)

1. Zastrzezenia patentowe Srodek grzybobójczy zawierajacy staly albo ciekly nosnik oraz substancje czynna, znamienny tym, ze jako substancje czynna zawiera N-podstawiony anilid kwasu karboksylowego o wzorze ogólnym 1, w którym Rl oznacza atom wodoru, grupe alkilowa o 1-4 atomach wegla, grupe alkoksylo wa o 1-3 atomach wegla albo atom chlorowca. R2 oznaza atom wodoru, grupe alkilowa, o 1-4 atomach wegla albo atom chlorowca, R3 oznacza grupe metylowa albo atom chloru, R4 oznacza ewentualnie pojedynczo lub kilkakrotnie podstawiona przez atom chlorowca grupe alkilowa o 1-6 atomach wegla, grupe alkenylowa o 2-4 atomach wegla, ewentualnie podstawiona pojedynczo lub kilkakrotnie atomem chlorowca w pierscieniu fenylowym grupe styrylowa, grupe cykloalkilowa o 3-6 atomach wegla, grupe benzylowa albo 1-fenyloetylowa, z wyjatkiem grupy monochlorowcoacetylowej, albo R4 oznacza grupe fenylowa, która jest ewentualnie pojedynczo albo dwukrotnie podstawiona grupe metylowa, atomem fluoru, chloru, bromu albo jodu, grupa cyjanowa, nitrowa, trójfluorometylowa, metoksylowa lub grua metylotio, albo ewentualnie pod¬ stawiona przez grupa metylowa lub atom chlorowca 5- albo 6-czlonowa grupe heterocykliczna o 1 albo 2heteroatomach, albo R4oznacza grupe—CH2—Ylub—CH(CH3)—Y, przy czym Y oznacza grupe alkoksylowa o 1-7 atomach wegla, grupe alkilotio o 1-4 atomach wegla albo ewentualnie podstawiona pojedynczo lub kilkakrotnie przez atom chloru, grupe metylowa, lub przez grupe trójfluorometylowa grupe fenoksylowa albo fenylotio, albo R4 oznacza —X—R5, przy czym X oznacza atom tlenu albo siarki, a R5 oznacza grupe alkilowa o 1-6 atomach wegla, grupe cyklohe- ksylowa albo grupe fenylowa, która jest ewentualnie pojedynczo lub kilkakrotnie podstawiona10 119636 atomem fluoru, chloru lub bromu, grupe trójfluorometylowa, metylowa, nitrowa, etylowa, izopro- pylowa, III-rzed.butylowa, metoksylowa albo grupa metylotio, Z oznacza grupy —CH2—, — CH2—(CH2)m—, —CH2—CH(CH3)— albo —CH(CH3)—CH2—, przy czym m oznacza liczbe 1 albo 2, natomiast A oznacza ewentualnie podstawiona pojedynczo lub kilkakrotnie przez grupe metylowa, etylowa, izopropylowa, nitrowa, atom chloru albo przez atom bromu grupe pirazolowa, imidazolowa albo 1,2,4-triazolowa, a n oznacza liczbe 0, 1 albo 2, jak równiez ich sole addycyjne z kwasami oraz zwiazki kompleksowe z metalami. Nr biezacy 1 1 2 3 4 5 6 7 8 9 10 11 v 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 Rl 2 CH, CHj C2H5 CH3 CH, CjH5 CHj CH, C2H5 CHj CH, CaH, CH, C2H3 C2H5 CH, CH, C2H5 C2H5 CH, CH, C2Hs CH, C2H5 CH, CH, C2H3 CH, CH, C2H5 CH, C2H5 CH, CH, CH, CH, CH, C2H3 CH, C2H, CH, CH, CH, CH, CH, CH, CH, Tabli R2 3 CH, C2H5 C2H5 CH, C2H5 C2H5 CH, C2H5 C2H5 CHj C2H, C2H, CH, C2H5 C2H5 CH, C2H5 C2H5 C2H5 CH, C2H5 C2H5 CH, C2H5 CH, C2H5 C2H5 CH, C2H5 C2H5 CH, Cns CH, CH, CH, CH, CH, C2H5 CH, C2H5 CH, CH, CH, CH, CH, CH, CH, i c a I R4 4 CH, CH, CH, C2H5 C2H, C2H5 CHh CHCI2 CHCI2 ca, ca, ca, CHCl—CH, CjHt—i C4H*-II—rzed cyklopropyl cyklopropyl cyklopropyl cykloproheksyl benzyl benzyl benzyl yeh:—C4H9- —III. rz. wzór 7 —CH2OCH, —CH2OCH3 —CH2'CH, —CH2—S—CH, _CH2—S—CH, —CH2—S—eh. CH2—O—C2H5 CH2-O— —CjHt—i wzór 8 wzór 9 —CH2—S— —CHt—i wzór 10 wzór 11 wzór 11 wzór 12 wzór 12 wzór 13 wzór 14 wzór 15 wzór 16 wzór 17 —CCI2—CH, -2-chlorobenzyl Stale fizyczne 5 gesta masa gesta masa olej olej olej olej 102-104°C 88-90°C olej 95°C 75-76°C olej 82°C olej olej 97-100°C 62-64 nD*= 1,5165 70°C olej krystaliczna masa 127°C olej 87°C 122-125°C 98-99°C1 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 2 CHj CHs C2H5 CH3 C2H5 CH3 C2H5 CjH, C2H5 C2H5 CjH, CH3 CHs C2H5 CjH* CHs CHs CHs CHs CHj C2H3 CHj C2H3 CHs CjHs CHs CH, CHs CHj CH3 C2H5 CH3 C2H, CHj C2H5 C2H5 CHj CH3 CH3 CH3 CH3 CH3 C2H5 C2H5 CH3 C2H5 CHj CH3 CH3 Cth C2H, CH3 C2H5 CH3 3 CH3 CH3 C2H5 CH3 C2H5 CH3 C2Hs C2Hs C2Hs C2H3 CH3 C2H5 C2H5 CH* CHs CHs CH, CH, CHs CH* CHs CHs CHs CHs CHs CHs CHs CHs CHs C2H, CH, C2H5 CHj C2H5 C2H5 CH3 CH3 CH, CH, CH3 CH, C2H3 C2H5 CH, C2H5 CH, CH3 CH3 CH3 CjHs CH, CHs CH, 4 3-chlorobenzyl of-fcnyloetyl o-fenyloetyl a-(2-chlorofeny- lo-etyl <*-(2-chlorofeny- lo)-etyl 4-chlorobcnzyl -CH=CH2 —CH=CH— —CHs wzór 4 —CCl=CHC1 -CH=<:(CHj)2 fenyl fenyl fenyl fenyl 2-metylofenyl 3-metylofcnyl 4-metylofenyl 2-chlorofenyI 3-cfalorofenyl 3-chksrofenyl 4-chlorofenyl 4-chlorofenyl 2-fluorofenyl 2-fluorofenyl 3-fluorofcnyl 4-fluorofenyl 3-bromofenyl 2-jodofenyl 3-cyjanofenyl 3-cyjanofenyl 2-nitrofcnyl 2-nitrofenyl 3-nitrofenyl 4-nitrofenyl 3-trójfluorome- tylofenyl 4-trójfluoro- metylofenyl 2-metoksyfenyl 3-metoksyfenyl 4-metoksyfenyl 4-metylotiofenyl 2,3-dwuchloro- fcnyl 2,3-dwuchloro- fenyl 2,4-dwuchloro- fenyl 2,4-dwuchloro- fenyl 2,5-dwuchloro- fenyl 3,5Klwuchloro- fenyl 3,5-dwumetylo- fenyl 2,6-dwufluoro- fenyl fury1-2 furyl-2 furyl-3 furyl-3 2,5-dwumetylo 11 furyl-3 5 nD23= 1,5547 nD23 = 1,6053 133°C 98-99°C 107-108°C U8-119°C 133-135°C 119-120°C 93°C 145°C 126°C 86-88°C 1!4-I15°C 141-143°C 116-118°C U2-114°C 205-207°C 15M54°C U8-120°C 63-64°C 108-109°C 107-108°C 92-93°C 68-69°C 108°C 125-126°C 69-70°C t roztworze przemiany bezposrednio balej12 119 636 Nr biezacy 1 1 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 Rl 2 2 C2Hs CH3 CH5 CH, CH, CH, CHj CH, C2H5 CH, CMs CH, CHj C2H5 C3H7—i CjHt-h H CHj CHj CHj C2H5 R2 3 3 C2H5 CHj C2H5 CHj CH3 CH3 CH, CH, C2H, CH, C2H5 CH, CHj C2Hi CjHt-I CHt-i H CH, CHj CHi C2H3 Tablica R5 4 4 2,5-dwumetylo- furyl-3 tienyl-2 tienyl-2 lienyl-3 jak 4-chlorotienyl-3 4,5-dwuchloro- tienyl-3 pirydyl-3 2-chloropirydyl-3 2-chloropirydyl-3 2,6-dwuchloropi- rydyl-4 2,6-dwuchloropi- rydyl-4 2,4-dwuchloropi- rydyl-5 wzór 18 wzór 18 tienyl-2 2,6-dwufluofo- fenyl j —CHr-OCH, CH2—CHj—Q 3-metyloizoksa- zolil-5 4-metyloksa- zolil-5 3-mctyloizoksa- zolil-5 II X 5 5 94-97°C .0 roztwór toluenowy przerabiany dalej I18°C 79-80°C 94-95°C 135°C olej olej 106°C 83-85°C 86-88°C Stale fizyczne (temperatura topnienia °C) 6 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 CH, C2H5 CH, C2H5 Ch, C2H5 C2H5 C2H5 C2H3 C2H5 C2H5 C2H5 CH, CH, C2H5 CHt—i CH, C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2HS C2H5 CH, CjHj CH, CzHs CH, C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 C2H5 CH, CH, C2H, C,H7-i CH, CjHj C2H5 C2H5 C2H5 C2H5 C2H5 C2H, C2H5 CH3 CH, C2H5 C2H5 C2H7—i CH,Hr-i n-C4H, II—rzcd.C4Ht izo—C4H9 III rzed.CJl, CH, fenyl cykloheksyl fenyl fenyl fenyl 4-fluorofenyl 2-chlorofenyl 2,4-dwuchlorofenyl 2,3-dwuchlorofenyl 3-chlorofenyl 4-chlorofenyl 2-metylo-4-chl orofenyl 2-chloro-5-metoksyfenyl 2,6-dwumetoksyfenyl O O O O 0 O O O O S S S O O 0 0 0 0 0 0 0 0 0 0 0 olej olej olej olej 113-115°C 94-95°C 115-116°C119 636 13 148 149 150 151 152 153 154 155 156 157 CtH5 CH3 CH, CH, CH3 CjH5 C2H5 C2H5 C2H5 CH3 C2H5 CH, C2HS C2H5 C2H3 C2H5 C2H5 C2H5 C2H3 CH3 3,5-dwumetoksyfenyl 3.5-dwuchlorofenyl 3-trójlluorometylofenyl 2,3-d wubromofenyl 4-nitrofenyl 4-izopropylofenyl 4-IH-rzed.butylofenyl 4-metylotiofenyl 2-mctylofenyl 3-metylofenyl O O O O O 0 O O O O Nr • biezacy ilT 159 160 161 162 R1 CH, CH, CHj CH, CH, R2 CH, CH, CH, CH, CH, Tablica III Z A —CHiCH,)-CH2— 1,2,4-triazol -CHj{CH,)-CHj- —CHj-i—CHj— —CHj—CHj—CHj- —CHa—CH(CH,- imidazol pirazol pirazol 1,2,4—triazol Sute fizyczne (temperatura wrzenia °C) 145°C/0,2 123-126°C/0,03 I45-150°C/Q,3 Tablica IV Nr biezacy 1 163 164 168 172 174 176 177 178 179 180 181 182 183 184 185 186 187 189 190 191 192 193 194 195 197 198 202 203 204 232 233 234 255 236 237 Ri 2 CH3 CH, C2H5 CH, CH, C2H, CH, CH, CH, CH, CH, CH, CH, CH, CH, CH, C2H5 CH, C2H5 CH, CH, CH, CH, CH, CH, CH, CH, CH, CH, H H CH, CH, CH, C2H5 Rj 3 CH, CH, CH, CH, C2H5 C2H5 CH3 CH, CH, CH, CH, CH, CH, C2H5 C2H5 C2H5 C2H5 CjH, CjH3 CH, CH, CH, CH, CH, CH, CH5 CH, CH, CH, H H CH, CH, CH, CjH, Z 4 CH2 CH2 CH2 CH2 CHj CH2 CHj CH2 CH2 CH2 CHj CHj CHj CH2 CHj CH, CHj CHj CHj CH2 -(CHj), wzór 26 wzór 26 CHj CHj CHj CHj CH2 CHj CHj CHj CHj CHj CHj CHj R4 5 CH, CH, CH, CjH, CjH, CjH, —CHC1—CH, -CHC1-CH, —CHC1—CH, —CHCI2 -CHClj —CHCIj - A 6 pirazol 1,2,4-triazol pirazol l,2,4»triazol 1,2,4-triazol M pirazol imidazol 1,2,4-triazol pirazol imidazol 1,2,4-triazol —CHCh 3,Sdwumetylopirazol —CHClj —CHClj —CHCtj -CHClj CO, C2H5 CjH, CHClj CHClj CHj—O—CH, -OCH, —OCH, —OCjH, wzór 27 wzór 27 wzór 27 —CHJ-OCH3 —CHj-OCH, —CHj-OCH, -CHj—OCH, —CHj-OCH, —CHj—OCH, pirazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol pirazol pirazol pirazol 1,2,4-triazol 1,2,4-triazol pirazol 1,2,4-triazol 1,2,4-triazol pirazol imidazol 1,2,4-triazol pirazol l,i4-triazol pirazol imidazol 1,2,4-triazol pirazol State fizyczne (temperatura topnienia °C) 7 92 100 61 103 68 80 95 119 131 98 118-121 133 124 57-59 121 96 108 87 135/0.1 94-96 76 128 106 91-94 110 57-59 91-92 zywica 112-114 84 76 113 nPM«
1.582 87 7414 119 636 1 240 241 242 243 244 246 247 248 250 251 252 255 264 266 267 268 269 270 271 279 286 287 288 289 290 291 292 293 294 295 296 297 298 299 300 301 305 306 308 309 310 311 312 313 314 315 316 317 319 320 321 322 323 324 325 326 327 330 331 332 333 334 335 336 337 338 339 2 CH« CH, CH3 CiHs C2H5 CH3 CH3 C:H, C2H, CH, CHj CH3 CH3 CH3 CH, CaH5 C2H5 CiH3 C2H3 C2G5 C2H5 C2H5 C2H5 CjH, C2H5 CH3 CH, CH3 C2H, C2H5 C2H, C2H, CH, CH, CH3 CHj CH3 CH3 CH3 CH3 CH3 CHj CH3 CH, CH3 CH, CH, CH3 CH, CH, CH, CHj CHj C2H5 CiH, CH, CH, CH, CH,bl C2H5 C2H5 C2H5 C2H5 CH, CH, C2H, C2H5 3 CH, CH, CH, C2H5 C2H5 CH, C2IU C2H5 CiH, CH, CH, CH, CH, CH, CH, C2H5 CjHs C2H5 C2H5 C2Hj -CHri C2H5 C2H5 C2H5 C2H5 CHj CH, CH, C2H2 C2H5 C2H5 C2H5 CH, CH, CH2 CH, CH, CH3 CH, CH3 CH, CH, CH, CH, CH, CH, CH, CH, CH, CH, CHj CH, CH, C2H5 CjH, CH, CH, CH, CH, C2H5 C2H5 C2H5 C2H5 CH, CH, C2Hs C2H5 4 CH2 CH2 CH: CH2 CH2 CH2 CH5 CH2 CH2 CH2 CH2 CH, CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CHj CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CHj CHj CH2 CH2 CH2 CH2 CH2 CH2 5 —CH2—S—CH3 —CH2—S-CH, —CH2—S—CH, —CH2—S—CHj —CH:—S—CH, cyklopropyl cykl 0propyl cyklopropyl cyklopropy! hcnzyl benzyl CH2—C4Hf-III. rzed wzór 11 wzór 12 wzór 12 wzór 12 wzór 12 wzór 12 wzór 12 wzór 28 1,2,4-triazol —C4H»-III— rzed. -C«Hr-ItI—ned. cykloheksyl cykloheksyl fenyl fenyl fenyl fenyl fenyl fenyl fenyl fenyl 2-metylofenyl 2-metylofenyl 2-metylofenyl 4-metylofenyl 4-metylofenyl 3-chlorofenyl 3-chlorofenyl 4-chlorofenyl 4-chlorofenyl 2-fluorofenyl 2-fluorofenyl 3-fluorofenyl 3-fluorofenyl 4-fluorofenyl 4-tluorofenyl 2-jodofenyl 2-jodofenyl 2-jodofenyl 3-cyjanofenyl 3-cyjanofenyl 3-cyjanofenyl 3-cyjanofenyl 2-nitrofenyl 2-nitrofenyl 3-nitrofenyl 3-nitrofenyl 4-nitrofenyl 4-nitrofenyl 3—CFrfenyl 3—CFrfenyl 4—CFrfenyl 4—CFrfenyl 2,4—Clrfenyl 2,4—Clz-fenyl 6 pirazol imidazol l,2,4triazol pirazol 1,2,4-triazol 1,2,4-triazol 1,2,4-triazol pirazol 1,2,4-triazol imidazol 1,2,4-triazol 1,2,4-triazol 1,2,4-triazol imidazol 1,2,4-triazol pirazol imidazol 4,5-dwuchloroimidazol 1,2,4-triazol 1,2,4-triazol 70 1,2,4-triazol imidazol imidazol imidazol pirazol imidazol 1,2,4-triazol pirazol imidazol 4,5-dwuchloroimidazol 1,2,4-triazol 4,5-dwuchloroimidazol imidazol 1,2,4-triazol pirazol imidazol l,2,4triazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol pirazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol imidazol 1,2,4-triazol imidazol l,2,4triazol imidazol 1,2,4-triazol pirazol imidazol 7 96 103 60 86 79 87 80 52 47 117-118 40 92-93 110-112 147-149 178-181 140 73 117 145 86-88 68 76 100 102 121-125 128 135 108 123 134 112-115 194 129-130 190-192 182-184 180 162-165 151 114-116 155-156 131-132 147-149 117-120 105-108 122-124 138-139 104-105 211-212 154-155 222-223 104-106 147-149 116-118 126-128 127-129 175-180 146-148 113-115 97-100 117-120 88-90 95-97 200-202 160-163 145 119119 636 15 12 3 4 5 6 7 340 341 345 346 347 348 349 350 352 354 355 356 357 358 359 360 361 362 364 365 366 367 382 383 C2H5 C2IU CH* C3H71 CjHtI C3H71 C2H5 CH* C2H5 CH3 CHj C2H5 C2H5 CHj CHj CH, CH, CH3 CjH7 CjH,i C2H7 CH, C2H5 C2H5 CiHj C2H5 CjHtI C3H71 CjH* C1H71 C2H5 C3H71 CjHj CH3 (CH,)3 C2H5 C2H5 CH3 CH3 CH3 CH3 CHj C3H7I CjH* C2H, CHj C2H7 C2Hj CH2 CHi CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 pirazol CH2 CH2 wzór 26 ** 41 • PL PL PL
PL1979220417A 1978-12-18 1979-12-14 Fungicide PL119636B2 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19782854598 DE2854598A1 (de) 1978-12-18 1978-12-18 N-substituierte carbonsaeureanilide, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide

Publications (3)

Publication Number Publication Date
PL220417A2 PL220417A2 (pl) 1980-12-15
PL119636B2 PL119636B2 (en) 1982-01-30
PL119636B1 true PL119636B1 (pl) 1982-01-31

Family

ID=6057522

Family Applications (1)

Application Number Title Priority Date Filing Date
PL1979220417A PL119636B2 (en) 1978-12-18 1979-12-14 Fungicide

Country Status (15)

Country Link
EP (1) EP0013360B1 (pl)
JP (1) JPS5592374A (pl)
AT (1) ATE821T1 (pl)
AU (1) AU5385779A (pl)
BR (1) BR7908221A (pl)
CS (1) CS214681B2 (pl)
DD (1) DD147992A5 (pl)
DE (2) DE2854598A1 (pl)
DK (1) DK536679A (pl)
IL (1) IL58852A0 (pl)
MA (1) MA18679A1 (pl)
NZ (1) NZ192428A (pl)
PL (1) PL119636B2 (pl)
SU (1) SU906346A3 (pl)
ZA (1) ZA796831B (pl)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0029011A1 (de) * 1979-11-13 1981-05-20 Ciba-Geigy Ag N-(Azolyl-1-äth-1'-yl)-halogenacetanilide, ihre Herstellung und ihre Verwendung als Herbizide
DE3014157A1 (de) * 1980-04-12 1981-10-22 Hoechst Ag, 6000 Frankfurt Fungizide, heterocyclisch substituierte thioglykolsaeureanilide
AR227948A1 (es) * 1980-12-01 1982-12-30 Monsanto Co 2-halogenoacetamidas herbicidas y composiciones herbicidas que las contienen
FR2499077A1 (fr) * 1981-02-05 1982-08-06 Ciba Geigy Ag Derives de l'aniline, leur preparation et produits microbicides en contenant
EP0117462A3 (en) * 1983-02-28 1986-08-20 American Cyanamid Company N-(2-4-(1h-imidazol-1-yl)alkyl)arylamides
ZA84949B (en) * 1983-04-06 1984-09-26 American Cyanamid Co Substituted-n-(2-4-(1h-imidazol-1-yl)alkyl)substituted amides
US4568685A (en) * 1984-02-29 1986-02-04 American Cyanamid Company N-[(1H-1,2,4-Triazol-1-yl)alkyl]-arylamides
US4966908A (en) * 1988-03-21 1990-10-30 Ciba-Geigy Corporation Isonicotinic acid amides for protecting plants against disease
US6906069B1 (en) 1999-01-08 2005-06-14 Amgen Inc. LXR modulators
ATE391123T1 (de) * 1999-11-15 2008-04-15 Janssen Pharmaceutica Nv Triazole als farnesyl-transferase-hemmer
AU2000235960A1 (en) * 2000-02-14 2001-08-27 Tularik, Inc. Lxr modulators
CA2474702A1 (en) 2002-01-30 2003-08-07 Tularik Inc Heterocyclic arylsulfonamidobenzylic compounds
MX2008012404A (es) * 2006-03-28 2008-10-09 Novartis Ag Derivados de amida y su aplicacion para el tratamiento de enfermedades relacionadas con proteina-g.
RU2616603C2 (ru) * 2015-07-22 2017-04-18 Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Образования "Уфимский Государственный Университет Экономики И Сервиса" 2-фенилтиометил замещенные 1,3-дикетоны и диметилмалонат - средства с фунгицидной активностью

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2648008C3 (de) * 1976-10-23 1980-09-04 Basf Ag, 6700 Ludwigshafen Acetanilide
DE2704281A1 (de) * 1977-02-02 1978-08-03 Bayer Ag N-substituierte halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
DE2828293A1 (de) * 1978-06-28 1980-01-10 Bayer Ag N-dichloracetyl-1,2,3,4-tetrahydro- chinaldin, verfahren zu dessen herstellung und dessen verwendung zur verhuetung von herbizidschaeden an kulturpflanzen
DE2830764A1 (de) * 1978-07-13 1980-01-31 Basf Ag Acetanilide
DE2835156A1 (de) * 1978-08-10 1980-02-14 Bayer Ag Substituierte n-pyrazolylmethyl -halogenacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide

Similar Documents

Publication Publication Date Title
PL119636B1 (pl)
US4315016A (en) Heterocyclic triazolylethyl ether compounds and their use as pesticides
PL153108B1 (en) Method for manufacturing acrylic acid derivatives
PL162219B1 (pl) Sposób wytwarzania nowych pochodnych kwasu propenowego PL PL PL PL PL PL
EP1318140B1 (en) Novel amide derivatives and medicinal use thereof
KR20050025189A (ko) 화학 화합물
IL235396A (en) Catechol o-methyltransferase activity inhibiting compounds
SK278282B6 (en) Benzyloximeter derivatives and their manufacturing method, fungicidal agent containing these compounds as active substances as well as application of these compounds in the agriculture
JPH03503056A (ja) アクリル酸誘導体
Tweit et al. Synthesis of antimicrobial nitroimidazolyl 2-sulfides,-sulfoxides, and-sulfones
SK287527B6 (sk) 1,2-Diarylbenzimidazoly a ich farmaceutické použitie
US4568376A (en) Herbicidal 5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran and derivatives thereof
DE2854598A1 (de) N-substituierte carbonsaeureanilide, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
US4394380A (en) 2-(2-Alkoxyalkyl)-1,2,4-triazole compounds and their use as fungicides
PL90030B1 (pl)
SK98296A3 (en) Process for the preparation of arylacetic ester derivatives and intermediate products in this process
US4067989A (en) 1,3-Diazole heterocyclic compounds and their use as pesticides
CS233739B2 (en) Fungicide agent and processing of effective component
EP1129083A1 (en) Isothiazolecarboxylic acid derivatives
SG172895A1 (en) Phenylimidazole compounds
JP2002293764A (ja) アミノエタノール誘導体
US4639447A (en) Azolylnitriles, and fungicides containing these compounds
JPH05194430A (ja) 殺菌性２−アリール−２−シアノ−２−（ヘテロサイクリルアルキル）エチル−１，２，４−トリアゾール類
PL128997B1 (en) Process for preparing novel,2- and 4-substituted 5-thiazolocarboxylic acids and their esters
AU610746B2 (en) 1-halo-1-azolylpropenes and -methyloxiranes and fungicides containing these compounds