DK1516874T3 - Fungicide heterocykliske aromatiske amider og sammensætninger, fremgangsmåder til anvendelse deraf og fremstilling deraf - Google Patents

Fungicide heterocykliske aromatiske amider og sammensætninger, fremgangsmåder til anvendelse deraf og fremstilling deraf Download PDF

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DK1516874T3
DK1516874T3 DK04027006.8T DK04027006T DK1516874T3 DK 1516874 T3 DK1516874 T3 DK 1516874T3 DK 04027006 T DK04027006 T DK 04027006T DK 1516874 T3 DK1516874 T3 DK 1516874T3
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alkyl
mmol
mixture
hydroxy
substituted
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Michael J Ricks
William H Dent Iii
Richard B Rogers
Chenglin Yao
Bassam S Nader
John L Miesel
Gina M Fitzpatrick
Kevin G Meyer
Noormohamed M Niyaz
Irene M Morrison
Robert P Gajewski
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Dow Agrosciences Llc
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    • 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
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    • 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
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
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    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
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Claims (9)

1. Heterocyklisk aromatisk amid med formlen I:
Formel I hvor: a)
betegner en 6-leddet heterocyklisk aromatisk ring, hvor Xi er N, X2 og X3 er CH, og X4 er CH, COMe, CMe, CCI, COEt eller CSMe; b) Z er O, S eller NORz, hvor Rz er H eller (C-i-C3)alkyl; og c) A betegner (i) (C3-Ci4)cycloalkyl, som indeholder 0-3 heteroatomer og 0-2 umættetheder, og som er substitueret med halogen, hydroxy, (Ci-C6)alkyl, (Ci-C6)halogenalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, (Ci-C6)alkylthio, arylthio, heteroa-rylthio, (Ci-C6)alkoxy, (Ci-C6)halogenalkoxy, (Ci-Cs)acyloxy, aryl, heteroaryl, (Ci-C6)acyl, (Ci-C6)carboalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (Ci-C6)alkylgrupper, eller (ii) et bi- eller tricyklisk (C6-Ci4)ringsystem, som indeholder 0-3 heteroatomer og 0-2 umættetheder, og som er substitueret med halogen, hydroxy, (Ci-C6)alkyl, (Ci-C6)halogenalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, (Ci-C6)alkylthio, arylthio, heteroarylthio, (Ci-C6)alkoxy, (Ci-C6)halogenalkoxy, (Ci-Cs)acyloxy, aryl, heteroaryl, (Ci-C6)acyl, (Ci-C6)carboalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (Ci-C6)alkylgrupper, hvor alkyl-, alkenyl- og alkynylgrupper er usubstitueret eller substitueret med en eller flere grupper valgt blandt halogen, hydroxy, cyano, nitro, aroyl, aryloxy, aryl, arylthio, heteroaryl, heteroaryloxy, heteroarylthio, (Ci-C8)acyl, (Ci-C6)halogenal-kyl, (Ci-C6)alkoxy, (Ci-C6)halogenalkoxy, (Ci-C6)alkylthio, (Ci-C6)halogenal-kylthio, carboaryloxy, carboheteroaryloxy, (Ci-C6)carboalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (Ci-C6)alkylgrupper; hvor arylgrupper er phenyl- eller naphthylgrupper, og heteroarylgrupper er 5- eller 6-leddede aromatiske ringe, som indeholder et eller flere heteroatomer, og hvor heteroaromatiske ringe kan være kondenseret med andre aromatiske systemer, hvor aryl- og heteroarylgrupper er usubstitueret eller substitueret med en eller flere grupper valgt blandt nitro, (Ci-C6)alkyl, (Ci-C6)halogenalkyl, (C3-C6)cycloal-kyl, (C2-C6)alkenyl, (C2-C6)alkynyl, aryl, heteroaryl, halogen, hydroxy, (Ci-C6)al-koxy, (Ci-C6)halogenalkoxy, (Ci-C6)alkylthio, (Ci-C6)alkylsulfonyl, (Ci-C6)al-kylsulfinyl, (Ci-C6)0C(0)alkyl, 0C(0)aryl, (C3-C6)OC(0)cycloalkyl, (Ci-C6)NHC-(O)alkyl, (C3-C6)NHC(0)cycloalkyl, NHC(0)aryl, NHC(0)heteroaryl, (C3-C6)cyc-loalkylthio, (C3-C6)cycloalkylsulfonyl, (C3-C6)cycloalkylsulfinyl, aryloxy, heteroaryloxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl, C(0)Ry, C(NORx)Ry, hvor Ry og Rx uafhængigt er H, (Ci-C6)alkyl, (C2-C6)alkenyl, (C3-C6)cycloalkyl, aryl eller heteroaryl, hvor en hvilken som helst alkyl- eller cycloalkylholdig substituent kan være substitueret med et eller flere halogenatomer; med det forbehold, at følgende forbindelser er udelukket: -3-hydroxy-4-methoxy-N-(1 '-benzylpiperidin-4'-yl)picolinamid; -(2'-irans)-3-hydroxy-4-methoxy-N-(2'-methylcyclohexyl)picolinamid; -(2'-c/s)-3-hydroxy-4-methoxy-N-(2'-methylcyclohexyl)picolinamid; -3-hydroxy-4-methoxy-N-(4'-methylcyclohexyl)picolinamid; -3-hydroxy-4-methoxy-N-(4'-hydroxycyclohexyl)picolinamid og -3-hydroxy-4-methoxy-N-(2'-hydroxycyclohexyl)picolinamid.
2. Forbindelse ifølge krav 1, hvor A er en (C3-Ci4)cycloalkylgruppe, som indeholder 0-3 heteroatomer og 0-2 umættetheder, og som er substitueret med halogen, hydroxy, (Ci-C6)alkyl, (Ci-C6)halogenalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, (Ci-Ce)alkylthio, arylthio, heteroarylthio, (Ci-C6)alkoxy, (Ci-C6)halo-genalkoxy, (Ci-C8)acyloxy, aryl, heteroaryl, (Ci-C6)acyl, (Ci-C6)carboalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (Ci-C6)alkylgrupper.
3. Forbindelse ifølge krav 1, hvor A er et bi- eller tricyklisk (C6-Ci4)ringsystem, som indeholder 0-3 heteroatomer og 0-2 umættetheder, og som er substitueret med halogen, hydroxy, (Ci-C6)alkyl, (Ci-C6)halogenalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, (Ci-C6)alkylthio, arylthio, heteroarylthio, (Ci-C6)alkoxy, (Ci-C6)halogenalkoxy, (Ci-C8)acyloxy, aryl, heteroaryl, (Ci-C6)acyl, (C-i-C6)car-boalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (C-i-C6)alkylgrupper.
4. Forbindelse ifølge krav 1, hvor Z er O.
5. Forbindelse ifølge krav 1, hvor Z er O, og A er en (C3-Ci4)cycloalkylgruppe, som indeholder 0-3 heteroatomer og 0-2 umættetheder, og som er substitueret med halogen, hydroxy, (Ci-C6)alkyl, (Ci-C6)halogenalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, (C-i-C6)alkylthio, arylthio, heteroarylthio, (Ci-C6)alkoxy, (Ci-C6)halogenalkoxy, (Ci-C8)acyloxy, aryl, heteroaryl, (Ci-C6)acyl, (C-i-C6)car-boalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (C-i-C6)alkylgrupper.
6. Forbindelse ifølge krav 1, hvor Z er O, og A er et bi- eller tricyklisk (Ce-Cu)- ringsystem, som indeholder 0-3 heteroatomer og 0-2 umættetheder, og som er substitueret med halogen, hydroxy, (Ci-Ce)alkyl, (Ci-Ce)halogenalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, (Ci-C6)alkylthio, arylthio, heteroarylthio, (Ci-Ce)alkoxy, (Ci-C6)halogenalkoxy, (Ci-C8)acyloxy, aryl, heteroaryl, (Ci-C6)acyl, (Ci-C6)carboalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (Ci-C6)alkylgrupper.
7. Fungicid sammensætning, som omfatter forbindelserne ifølge krav 1 og en fytologisk acceptabel bærer.
8. Sammensætning ifølge krav 7, som endvidere indbefatter mindst én anden forbindelse valgt fra gruppen bestående af insekticider, fungicider, herbicider, ne-maticider, acaricider, artropodicider, baktericider og kombinationer deraf.
9. In wYro-fremgangsmåde til bekæmpelse eller forebyggelse af svampeangreb, hvilken fremgangsmåde omfatter påføring på det sted, hvor svampen befinder sig, eller det sted, hvor angrebet skal bekæmpes eller forebygges, af en fungicidt effektiv mængde af et heterocyklisk aromatisk amid med formlen I:
Formel I hvor: a)
betegner en 6-leddet heterocyklisk aromatisk ring, hvor Xi er N, X2 og X3 er CH, og X4 er CH, COMe, CMe, CCI, COEt eller CSMe; b) Z er O, S eller NORz, hvor Rz er H eller (Ci-C3)alkyl; og c) A betegner (i) (C3-Ci4)cycloalkyl, som indeholder 0-3 heteroatomer og 0-2 umættetheder, og som er substitueret med halogen, hydroxy, (C-i-CeJalkyl, (C-i-CeJhalogenalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, (Ci-C6)alkylthio, arylthio, hetero-arylthio, (Ci-C6)alkoxy, (Ci-C6)halogenalkoxy, (Ci-C8)acyloxy, aryl, heteroaryl, (Ci-C6)acyl, (Ci-C6)carboalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (Ci-C6)alkylgrupper, eller (ii) et bi- eller tricyklisk (C6-Ci4)ringsystem, som indeholder 0-3 heteroatomer og 0-2 umættetheder, og som kan være usubstitueret eller substitueret med halogen, hydroxy, (Ci-C6)alkyl, (Ci-C6)halogenalkyl, cyano, nitro, aroyl, aryloxy, heteroaryloxy, (Ci-C6)alkylthio, arylthio, heteroarylthio, (Ci-C6)alkoxy, (Ci-C6)halo-genalkoxy, (Ci-C8)acyloxy, aryl, heteroaryl, (Ci-C6)acyl, (Ci-C6)carboalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (Ci-C6)alkylgrupper, hvor alkyl-, alkenyl- og alkynylgrupper er usubstitueret eller substitueret med en eller flere grupper valgt blandt halogen, hydroxy, cyano, nitro, aroyl, aryloxy, aryl, arylthio, heteroaryl, heteroaryloxy, heteroarylthio, (Ci-C8)acyl, (Ci-C6)halogenal-kyl, (Ci-C6)alkoxy, (Ci-C6)halogenalkoxy, (Ci-C6)alkylthio, (Ci-C6)halogenal-kylthio, carboaryloxy, carboheteroaryloxy, (Ci-C6)carboalkoxy eller amid, som er usubstitueret eller substitueret med en eller to (Ci-C6)alkylgrupper; hvor arylgrupper er phenyl- eller naphthylgrupper, og heteroarylgrupper er 5- eller 6-leddede aromatiske ringe, som indeholder et eller flere heteroatomer, og hvor heteroaromatiske ringe kan være kondenseret med andre aromatiske systemer, hvor aryl- og heteroarylgrupper er usubstitueret eller substitueret med en eller flere grupper valgt blandt nitro, (Ci-C6)alkyl, (Ci-C6)halogenalkyl, (C3-C6)cycloal-kyl, (C2-C6)alkenyl, (C2-C6)alkynyl, aryl, heteroaryl, halogen, hydroxy, (Ci-C6)al-koxy, (Ci-C6)halogenalkoxy, (Ci-C6)alkylthio, (Ci-C6)alkylsulfonyl, (Ci-C6)al-kylsulfinyl, (Ci-C6)0C(0)alkyl, 0C(0)aryl, (C3-C6)OC(0)cycloalkyl, (Ci-C6)NHC-(O)alkyl, (C3-C6)NHC(0)cycloalkyl, NHC(0)aryl, NHC(0)heteroaryl, (C3-C6)cyc-loalkylthio, (C3-C6)cycloalkylsulfonyl, (C3-C6)cycloalkylsulfinyl, aryloxy, heteroaryloxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl, C(0)Ry, C(NORx)Ry, hvor Ry og Rx uafhængigt er H, (Ci-C6)alkyl, (C2-C6)alkenyl, (C3-C6)cycloalkyl, aryl eller heteroaryl, hvor en hvilken som helst alkyl- eller cycloalkylholdig substituent kan være substitueret med et eller flere halogenatomer; med det forbehold, at følgende forbindelser er udelukket: -3-hydroxy-4-methoxy-N-(1 '-benzylpiperidin-4'-yl)picolinamid; -(2'-frans)-3-hydroxy-4-methoxy-N-(2'-methylcyclohexyl)picolinamid; -(2'-c/s)-3-hydroxy-4-methoxy-N-(2'-methylcyclohexyl)picolinamid; -3-hydroxy-4-methoxy-N-(4'-methylcyclohexyl)picolinamid; -3-hydroxy-4-methoxy-N-(4'-hydroxycyclohexyl)picolinamid og -3-hydroxy-4-methoxy-N-(2'-hydroxycyclohexyl)picolinamid.
DK04027006.8T 1999-07-20 2000-07-20 Fungicide heterocykliske aromatiske amider og sammensætninger, fremgangsmåder til anvendelse deraf og fremstilling deraf DK1516874T3 (da)

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