PL107047B1 - Srodek grzybobojczy i nicieniobojczy - Google Patents
Srodek grzybobojczy i nicieniobojczy Download PDFInfo
- Publication number
- PL107047B1 PL107047B1 PL1977199031A PL19903177A PL107047B1 PL 107047 B1 PL107047 B1 PL 107047B1 PL 1977199031 A PL1977199031 A PL 1977199031A PL 19903177 A PL19903177 A PL 19903177A PL 107047 B1 PL107047 B1 PL 107047B1
- Authority
- PL
- Poland
- Prior art keywords
- triazolyl
- phenyl
- propane
- dimethyl
- diphenyl
- Prior art date
Links
- -1 alkyl radical Chemical group 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 7
- JCFCCMVWFCHPFT-UHFFFAOYSA-N 4-benzhydryl-2h-triazole Chemical compound N1N=NC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 JCFCCMVWFCHPFT-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 239000005645 nematicide Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000001294 propane Substances 0.000 description 32
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 11
- 239000001273 butane Substances 0.000 description 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 101100203596 Caenorhabditis elegans sol-1 gene Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 244000000008 fungal human pathogen Species 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- MHOVAHRLVXNVSD-RNFDNDRNSA-N rhodium-107 Chemical group [107Rh] MHOVAHRLVXNVSD-RNFDNDRNSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
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- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Przedmiotem wynalazku jest srodek grzybobój¬ czy i nicieniobójczy zawierajacy jako substancje czynna dwufenylotriazolilometany.Wiadomo, ze trytylo-l,2,4-triazole, np. trójfeny- lo-/l,2,4-triaziolilo-l/-metan maja dobre dzialanie grzybobójcze (opis patentowy RFN DOS nr 1 795 249). Ich dzialanie, zwlaszcza w nizszych daw¬ kach i stezeniach nie zawsze jest zadowalajace.Stwierdzono, ze dwufenylo-triazolilometany o wzorze 1, w którym R oznacza rodnik alkilowy, grupe alkilokarbonylowa lub ewentualnie podsta¬ wiona grupe fenylokarbonyIowa X i Y oznaczaja atomy chlorowców, rodniki alkilowe, chlorowcoal- kilowe, grupy alkoksylowe, alkilotio ewentualnie podstawione rodniki fenylowe i fenoksylowe, gru¬ py nitrowe lub cyjanowe i w tym zakresie zna¬ czen moga miec takie same lub rózne znaczenie i m i n oznaczaja liczby calkowite 0—5, oraz ich sole tolerowane przez organizm maja silne dzia¬ lanie grzybobójcze i nicieniobójcze.Dwufenylo-triazolilo-metany o wzorze ogólnym 1 sa pochodnymi 1,2,4-triazolu, w których reszta aizolu zwiazana jest polozeniem 1 lub 4.Niespodziewanie substancje czynne srodka we¬ dlug wynalazku maja znacznie lepsze dzialanie grzybobójcze niz znane trytylo-l,2,4-triazole, na przyklad trójfenylo-/l,2,4-triazolilo-l/-metan.Niespodziewane jest równiez dodatkowe dziala¬ nie nicieniobójcze. Wzbogacaja one zatem stan techniki. 10 15 20 23 Substancje czynne srodka wedlug wynalazku sa czesciowo znane z opisu patentowego RFN DOS nr 2 037 610, poniewaz sa objete przez wzór ogólny zwiazku. W opisie tym jest przedstawione wytwa¬ rzanie dwufenylo-triazolilometanów i ich zastoso¬ wanie jako leków.Natomiast zastosowanie dwufenylo-triazolilome¬ tanów jako fungicydów i nematycydów jest nowe i stwierdzone nieoczekiwanie, gdyz nie mozna by¬ lo tego przewidziec na podstawie znanego stanu techniki. Ze znanego stanu techniki jest powszech¬ nie wiadome, ze zwiazki, które skutecznie niszcza grzybice u ludzi i zwierzat nie znajduja w ogóle zastosowania w ochronie roslin przeciw grzybicom fitopatogennym i tez odwrotnie. Przyczyna tego jest znany i udowodniony fakt, ze grzyby fitopa- togenne naleza do innych klas i rzedów i wyka¬ zuja inne wlasciwosci niz grzyby humanopatogen- ne wystepujace u ludzi. Tak wiec leki przeciw- grzybicowe nie znajduja zastosowania jako srod¬ ki przeciwgrzybicowe w ochronie roslin i odwrot¬ nie srodki stosowane w ochronie roslin nie znaj¬ duja zastosowania w medycynie przy leczeniu grzybic.Ponadto zwiazki o wzorze 1 stanowiace sub¬ stancje czynna srodka wedlug wynalazku sa no¬ we, poniewaz nie zostaly one wymienione w opi¬ sie patentowym RFN DOS nr 2 037 610.Substancje czynne srodka przedstawia ogólnie wzór 1. We wzorze tym R oznacza korzystnie rod- 107 0473 16764? nik alkilowy o 1—4 atomach wegla lub grupe al- kilokarbonylowa o 1—4 atomach wegla, lub gru¬ pe fenylokarbonylowa ewentualnie podstawiona a- tomem chlorowca, zwlaszcza fluoru, chloru lub bro¬ mu i rodnikiem alkilowym o 1—2 atomach wegla, X i Y oznaczaja korzystnie atomy chlorowców, zwlaszcza fluoru, chloru lub bromu, proste lub roz¬ galezione rodniki alkilowe o 1—4 atomach we¬ gla, grupy chlorowcoalkilowe o 1—4 atomach we¬ gla i do 5 atomach chlorowca, zwlaszcza 1—2 a- tomach wegla i do 3 takich samych lub róznych atomach chlorowców, zwlaszcza fluoru i chloru, np. grupy trójfluorometylowe, ponadto korzystnie grupy alkoksylpwe i alkilotio o 1—2 atomach we- l-/4-fluorofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/-bu- tan, l-/3-metylofenylo/-l-fenylo-l-/l,2,4-triazolilo-l-/- -butan, 5 l-/3-trójfluorometylofenylo/-l-fenylo-l-/l,2,4-tria- zolilo-l/-butan, l,l-dwufenylo-2-metylo-l-/l,2,4-triazolilo-l/-pro- pan, l,l-dwufenylo-l-/l,2,4-triazolilo-l/-peinton, 10 l-/2-chlorofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- -pentan, l-/4-fluorofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- -pentan, l-/3-metylofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- gla, grupy fenylowe i fenoksylowe ewentualnie 15 -pentan, ptflSfcpwioner -atomami chlorowców, zwlaszcza fiu- l,l-dwufenylo-2-metylo-l-/l,2',4-triazolilo-l-/-bu- oi\i, chloru i fcrfenAi$ lub rodnikami alkilowymi o tan, 1 lub 2 atomach wegla, oraz korzystnie grupy ni- l-/4-chlorofenylo/-l-fenylo-2-metylo-l-/l,2,4-tria- trowe i cyjanowe, I*rzy czym X i Y w podanym zolilo-l/-butan, zakresie znaczen mofea miec takie same lub rózne 20 l-/4-fluorofenylo/-l-fenylo-2-metylo-l-/l,2,4-triazo- zlISczeTSle, nr i ntJEhaczaja korzystnie liczby cal¬ kowite 0—3, zwlaszcza 0—2.Substancjami czynnymi srodka sa np. nizej po¬ dane zwiazki; l,l-dwufenylo-I/l,2,4-triazolilo-l/etan, l,l-dwufenylo-l/l,2,4-tria2olilo-4/-etan, l-/4-chloxQfenylo-l-/l,2,4-triazolilo-l/-etan, l-/4-chIorofenylo/-l-fenylo-l-/l,2,4-triazolilo-4/-e- tan, l-/4-fluorofenylo/-l-fenylo-l-/l^,4-triazolilo-l/-e- tan, l-/2-metylofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/-e- tan, l^/3-tróifluOTometylofenylo/-l-fenylo-/l,2,4-tria2o- lilo-lAetan, l7/4^mfet6ksyfenylo/-l-fenylo-l-/l2,4-triazolilo-l/- -etan, l-/4-metylotiofenylo/-l^fenylo^l-/l,2,4-triazolik)*l/- -etan, l-/4-bifenylilo/-l-fenylo-l-/l,2,4-triazolilo-4-/-etan, l-/4-4'-chlorobifenylilo/-l-fenylo/-l-/l,2,4-triazolilo- -lAetan. l«/4-fenoksyie|iyloM-fenylo-l-/l,2,4-triazolilo-l/-e- tan, i;i-dwufetflylo-l-/l,2,4-triazolilo-l/-propan, l,l-dwufeiiylo-l-/l,2,4-triazoliló-4/^ptropan, ^ l-/4^hlOT^enylo/-l-fenylo-l-/l,2,4-triazolilo-l/-pro- pan, l-/4-chkrofenylo/-l-fenylo-l-/l,2,4-triazolilo-4-/pro- pan, l-/4-fluorofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/-pro- pan, l-/3-metylofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- ^propan, l-/3,4-dwumetylofenylo/-l-fe(nyIo-l-/l,2,4-triazoli- k)-l/-propan, l-/2,5^dwumetylofenylo/-l-fenylo-l-/l,2,4^triazoli- lo-l/-propan, l,l-dwufenylo-l-/l,2,4-triazplilo-l/-butan, l,i-dwufenylo-l-/l,2,4-triazolilo-4/-butan, l-/4-chIoxófenylo/-l-fenylo-l-/l,2,4-triazolilo-l/-bu- tan, l-/4-chlorofenylo/-l-fenylo-l-/l,2,4-tnazolilo-4/-bu- tan, lilo-l/-butan, l-/2-metylofenylo/-l-fenylo-2-metylo-l-/l,2,4-tria- zolilo-l/-butan, l-/2,4-dwumetylofenylo/-l-fenylo-2-metylo-l/l,2,4- 25 -triazolilo-l/-butan, l,l-dwufenylp-2,2-dwumetylo-l-/l,2,4-triazolilo-l/- -propan, l,l-dwufenylo-2,2-dwumetylo-l-/l,2,4-triazololo-4/- -propam, 30 l-/2-chlorofenylo/-l-fenylo-2,2-dwumetylo-l-/l,2,4- -triazolilo-l-/-propan, l-/2-chlorofenylo/-l-fenylo-2,2-dwumetylo-l-/l,2,4-- -triazolilo-4/-propan, l-/4-chloxofenylo/-l-fenylo-2,2-dwumetylo-l-/l,2,4- 35 -triazolilo-l/-propan, l-/4-chlorofenylo/-l-fenylo-2,2-dwumetylo-l-/l,2,4- -triazolilo-4-/-propan, l-/4-fluorofenylo/-l-fenylo-2,2-dwumetylo-l-/l,2,4- -tfiazolilo-l/-propan, 40 l-/3-trójfluorometylofenylo/-l-fenylo-2,2-dwume- tylo-l/-l,2,4-triazolilo-l/-propan, l-/2-metyloferiyloy-l-fenylo-2,2-dwumetylo-l-/l,2,4- -triazolilo-l/-propan, l-/3-metylofenylo/-l-fenylo-2,2-dwumetylo-l-/l,2,4- 45 -triazolilo-l/-propan, l-/4-metoksyfenylo/-l-fenylo-2,2-dwumetylo- -l/l,2,4-triazolilo-l/-propan, l-/4-etyloksyfenylo/-l-fenylo-2,2-dwumetylo-l- -/l,2,4-triazolilo-l-/-propan, bo l-/4-metylotiofenylo/-l-fenylo-2,2-dwumetylo-l- -/l,2,4-triazolik)-/l/-proran, * l-/4-chloro-3-metylofenylo/-l-fenylo-2,2-dwumety- lo-l-/-l,2,4-triazolilo-l/-propan, l-/3,4-dwumetylofenylo/-l-fenylo-2,2-dwumetylo- 55 -l-/l,2,4-triazolilo-l/-propan, l-/2,4-dwumetylofenylo/-l-fenylo-2',2-dwumetylo- -l/l,2,4-triazolilo-l/-propan, 1-/4-fenoksyfenylo/-1-fenylo-2,2-dwumetylo-1- -/l,2,4-triazolilo-l/-propan, '. -* 60 l-/4-4'-chlorofenoksyfenylo/-l-feinylo-2,2-dwume- tylo-l-/-l,2,4-triazolilo-l/-propan, l-/4-bifenylilo/-l-fenylo-2,2-dwumetylo-l-/l,2,4- -triazolilo-4/-propan, l-/4-4'-chlorobifenylilo/-l-fenylo-2,2-dwum^tylo- •5 -l/l,2,4-triazolilo-l/-propan,107 047 6 l-/2,4-dwuchlorofenylo/-l-fenylo-2,2-dwurnetylo-l- -/l,2,4-triazolilo-l/-propan, l-/4^itrofenylo/-l-fenylo-2,2-dwumetylo-l-/l,2,4- -triazolilo-l/-propan, l-/4-cyjanofenylo/-l-fenylo-2,2-dwumetylo-l-/l,2,4- -triazolilo-l/-propan, l-bis/4-chlorofenylo/-2,2-dwumetylo-l-/l,2,4-triazo- lilo-l/-propan, l-bis-/4-metylofenylo/-2,2-dwumetylo-l-/l,2,4-tria- zoliló-l/-propan, l-/4-chlarofenylo/-l-/4-fluorofenylo/-2,2-dwumety- lo-l/l,2,4-triazolilo-l/-propan, l-/4-fluorofenylo/-l-/4-fenoksyfenylo/-2,2-dwume- tylo-l/l,2,4-triazolilo-l/-propan, l-/4-bifenylilo/-l-/4-fenoksyfenylo/-2,2-dwumetylo- -l-/l,2,4-triazolilo-l/-proipan, l,l^wufenylo-l-/l,2,4-triazolilo-l/-propanon-2, l,l-dwufenylo-l-/l,2,4-triazolilo-4-/-propanon-2, l-/4-chlorofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- -propanon-2, l-/4-chlorofenylo/-l-fenylo-l-/l,2,4-triazolilo-4/- -propanon-2, l-/2,4-dwuchlorofeaiylo/-l-fenylo-l-/l,2,4-triazolilo- -l-/-propanon-2, l-/4-fluorofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/-pro- panon-2, l-/2-metylofenylo/-l-fenylo-l-/l,2,4-tóazolilo-l/- ^propanon-2, l-/3-trójfluoxometylofenylo/-l-fenylo-l-/l,2,4-tria- zolilo-l/-propanon-2, l-/.4-metoksyfenylo/-l-fanylo-l-/l,2,4-triazolilo-l/- -propanon-2, l-/4-metylotiofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- -propanon-2, l-/4-bifenylilo/-l-fenylo-l-/l,2,4-triazolilo-l/-pro- panon-2, l-/4-bifenylilo/-l-fenylo-l-/l,2,4-triazolilo-4/-pro- panon-2, l-/4-4'-chlorobifenylilo/-l-fenylo-l-/l,2,4-triazolilo- -l/-propanon-2, l-/4-fenoksyfenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- -propanon-2, l,l-dwuf€tiylo-l-/l,2,4-triazolilo-l/-butanon-2, 1,1 -dwufenylo-1-/1,2,4-triazolilo-4/-butanon-2, l-/4-chlorof€nylo/-l-fenylo-l-/l2,4-triazolilo-l/- -butainon-2, l-/4-chlorofenylo/-l-f€nylo-l-/l,2,4-triazolilo-4/-bu- tanon-2, l-/4-fluorofenylo/-l-fenylo-l-/l,2,4-triazolilo-l-/- -butanon-2, l-/3-metylofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- -butanon-2, l-/3,4-dwumetylofenylo/-l-fenylo-l-/l,2,4-triazoli- lo-l-/-butainoai-2, 1-/2,5-dwumetylofenylo/-1-fenylo-1-/l,2,4-triazoli- lo-l/-butanon-2, 1,1-dwufenylo-1-/l,2,4-triazolilo-l/-pentanon-2, 1,1-dwufenylo-1-/l,2,4-triazolilo-4/-pentanon-2, l-/4-chlorofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- -pantanon-2, l-/4-chlorofenylo/-l-fenylo-l-/l,2,4-triazolilo-4/- -pantanon-2, I-/4-fluorofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- -pantanon-2, 20 25 30 l-/3-metylofenylo/-l-fenylo-l-/l,2,4-triazolilo-l/- -pantanon-2, l-/3^ójfltj!oxometylofe9^ zolilo-l/-pentanon-2, 5 l,lniwufenylo-3-metylo-l-/l,2,4^riaz
Claims (1)
1. Zastrzezenie patentowe grodek grzybobójczy i nicieniobójczy, zawiera¬ jacy substancje czynna, nosnik i/lub substancje powiarzchniowo-czynne, znamienny tym, ze jako substancje czynna zawiera co najmniej jeden dwu- fenylo-triazolilo-metan o wzorze 1, w którym R oznacza rodnik alkilowy, grupe alkilokarbonylowa lub ewentualnie podstawiona grupe fenylokarbo- nylowa, X i Y oznaczaja atomy chlorowców, rod¬ niki alkilowe, grupy chlorowcoalkilowe, alkoksy- lowe, alkilotio, ewentualnie podstawione rodniki fenylowe i fenoksylowe, grupy nitrowe lub cyja- nowe i w podanym zakresie znaczen moga miec takie same lub rózne znaczenia, a symbole min oznaczaja liczby calkowite 0—5, i/lub jego sole to¬ lerowane przez organizm.107 047 Hzór 1 N- ^N ó Wzór 2 N Cl ^-C0-C(CH3)3 O Wzór3 O — C-CO-cfcH.) '3/3 O Hzór 4107 047 Kt,H O Hzcr 5 N- l O N.:6r 6 bN-3, zam. 59,80 Cena 45 zl PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2628152A DE2628152C2 (de) | 1976-06-23 | 1976-06-23 | Fungizide und nematizide Mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL199031A1 PL199031A1 (pl) | 1978-02-27 |
| PL107047B1 true PL107047B1 (pl) | 1980-01-31 |
Family
ID=5981242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1977199031A PL107047B1 (pl) | 1976-06-23 | 1977-06-21 | Srodek grzybobojczy i nicieniobojczy |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4140782A (pl) |
| JP (1) | JPS52156928A (pl) |
| AT (1) | AT354808B (pl) |
| AU (1) | AU507606B2 (pl) |
| BE (1) | BE855987A (pl) |
| BR (1) | BR7704038A (pl) |
| CA (1) | CA1093085A (pl) |
| CH (1) | CH625677A5 (pl) |
| CS (1) | CS192485B2 (pl) |
| DD (1) | DD131991A5 (pl) |
| DE (1) | DE2628152C2 (pl) |
| DK (1) | DK143993C (pl) |
| EG (1) | EG12727A (pl) |
| FR (1) | FR2355452A1 (pl) |
| GB (1) | GB1528564A (pl) |
| HU (1) | HU176918B (pl) |
| IL (1) | IL52345A (pl) |
| IT (1) | IT1080208B (pl) |
| NL (1) | NL7706778A (pl) |
| PL (1) | PL107047B1 (pl) |
| PT (1) | PT66683B (pl) |
| SE (1) | SE7707231L (pl) |
| SU (1) | SU663262A3 (pl) |
| TR (1) | TR19281A (pl) |
| ZA (1) | ZA773736B (pl) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0194064A3 (en) * | 1985-03-06 | 1988-11-17 | Imperial Chemical Industries Plc | Azolyl substituted aralkyl compounds |
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| US4749713A (en) * | 1986-03-07 | 1988-06-07 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
| GB8716650D0 (en) * | 1987-07-15 | 1987-08-19 | Ici Plc | Use of olefinic compounds |
| TW533205B (en) | 1996-06-25 | 2003-05-21 | Novartis Ag | Substituted 3,5-diphenyl-l,2,4-triazoles and their pharmaceutical composition |
| RU2363157C1 (ru) * | 2008-03-24 | 2009-08-10 | Федеральное государственное образовательное учреждение высшего профессионального образования "Горский государственный аграрный университет" | Способ защиты зерна от болезней при хранении |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2037610A1 (de) | 1970-07-29 | 1972-02-03 | Bayer Ag | Neue alpha-substituierte Benzyl-azole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
-
1976
- 1976-06-23 DE DE2628152A patent/DE2628152C2/de not_active Expired
-
1977
- 1977-06-15 US US05/806,889 patent/US4140782A/en not_active Expired - Lifetime
- 1977-06-16 CS CS773988A patent/CS192485B2/cs unknown
- 1977-06-17 PT PT66683A patent/PT66683B/pt unknown
- 1977-06-20 GB GB25653/77A patent/GB1528564A/en not_active Expired
- 1977-06-20 NL NL7706778A patent/NL7706778A/xx not_active Application Discontinuation
- 1977-06-20 IL IL52345A patent/IL52345A/xx unknown
- 1977-06-21 DD DD7700199615A patent/DD131991A5/xx unknown
- 1977-06-21 IT IT24913/77A patent/IT1080208B/it active
- 1977-06-21 CH CH761677A patent/CH625677A5/de not_active IP Right Cessation
- 1977-06-21 PL PL1977199031A patent/PL107047B1/pl unknown
- 1977-06-21 SU SU772497841A patent/SU663262A3/ru active
- 1977-06-22 FR FR7719114A patent/FR2355452A1/fr active Granted
- 1977-06-22 SE SE7707231A patent/SE7707231L/xx not_active Application Discontinuation
- 1977-06-22 DK DK275477A patent/DK143993C/da active
- 1977-06-22 BR BR7704038A patent/BR7704038A/pt unknown
- 1977-06-22 BE BE178677A patent/BE855987A/xx not_active IP Right Cessation
- 1977-06-22 ZA ZA00773736A patent/ZA773736B/xx unknown
- 1977-06-22 TR TR19281A patent/TR19281A/xx unknown
- 1977-06-22 EG EG367/77A patent/EG12727A/xx active
- 1977-06-22 AU AU26324/77A patent/AU507606B2/en not_active Expired
- 1977-06-22 CA CA281,120A patent/CA1093085A/en not_active Expired
- 1977-06-23 JP JP7395277A patent/JPS52156928A/ja active Granted
- 1977-06-23 AT AT443277A patent/AT354808B/de not_active IP Right Cessation
- 1977-06-23 HU HU77BA3546A patent/HU176918B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR19281A (tr) | 1978-10-27 |
| ATA443277A (de) | 1979-06-15 |
| BR7704038A (pt) | 1978-07-04 |
| EG12727A (en) | 1979-12-31 |
| JPS6139921B2 (pl) | 1986-09-06 |
| PT66683A (de) | 1977-07-01 |
| BE855987A (fr) | 1977-12-22 |
| NL7706778A (nl) | 1977-12-28 |
| PT66683B (de) | 1978-11-17 |
| ZA773736B (en) | 1978-05-30 |
| DE2628152A1 (de) | 1978-01-05 |
| DK143993B (da) | 1981-11-16 |
| DE2628152C2 (de) | 1985-03-28 |
| JPS52156928A (en) | 1977-12-27 |
| CA1093085A (en) | 1981-01-06 |
| AT354808B (de) | 1979-01-25 |
| DD131991A5 (de) | 1978-08-16 |
| US4140782A (en) | 1979-02-20 |
| DK275477A (da) | 1977-12-24 |
| FR2355452B1 (pl) | 1981-02-27 |
| HU176918B (hu) | 1981-06-28 |
| SU663262A3 (ru) | 1979-05-15 |
| AU2632477A (en) | 1979-01-04 |
| CH625677A5 (pl) | 1981-10-15 |
| IL52345A (en) | 1979-10-31 |
| SE7707231L (sv) | 1977-12-24 |
| IT1080208B (it) | 1985-05-16 |
| CS192485B2 (en) | 1979-08-31 |
| AU507606B2 (en) | 1980-02-21 |
| PL199031A1 (pl) | 1978-02-27 |
| IL52345A0 (en) | 1977-08-31 |
| DK143993C (da) | 1982-04-19 |
| FR2355452A1 (fr) | 1978-01-20 |
| GB1528564A (en) | 1978-10-11 |
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