US 5,962,436 AGranted

Fungicidal cyclic amides

AssigneeE. I. Du Pont de Nemours and Company

InventorsRichard James Brown, Deborah Ann Frasier, Constance Happersett, Peter Paul Castro, Charlene Gross Sternberg

Life of this patent

Estimating the term…

Abstract

Cyclic amides, including triazole containing cyclic amides, their N-oxides, agriculturally-suitable salts and compositions, and their methods of use as fungicides.

Claims10

Dependent claims

A compound selected from Formula I, N-oxides and agriculturally-suitable salts thereof, ##STR126## wherein:

W is O;
S;
NH;
N(C.sub.1 -C.sub.6 alkyl);
or NO(C.sub.1 -C.sub.6 alkyl);
X is OR.sup.1 ;
S(O).sub.m R.sup.1 ;
or halogen;
R.sup.1 is H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.2 -C.sub.4 alkylcarbonyl;
or C.sub.2 -C.sub.4 alkoxycarbonyl;
R.sup.2 is H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.2 -C.sub.4 alkylcarbonyl;
C.sub.2 -C.sub.4 alkoxycarbonyl;
hydroxy;
C.sub.1 -C.sub.2 alkoxy;
or acetyloxy;
R.sup.3 and R.sup.4 are each independently H;
halogen;
cyano;
nitro;
hydroxy;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.2 -C.sub.6 alkenyloxy;
C.sub.2 -C.sub.6 alkynyloxy;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 alkylsulfinyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
formyl;
C.sub.2 -C.sub.6 alkylcarbonyl;
C.sub.2 -C.sub.6 alkoxycarbonyl;
NH.sub.2 C(O);
(C.sub.1 -C.sub.4 alkyl)NHC(O);
(C.sub.1 -C.sub.4 alkyl).sub.2 NC(O);
Si(R.sup.25).sub.3 ;
Ge(R.sup.25).sub.3 ;
(R.sup.25).sub.3 Si--C.tbd.C--;
or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R.sup.8 and optionally substituted with one or more R.sup.10 ;
Y is --O--;
--S(O).sub.n --;
--NR.sup.6 --;
--C(.dbd.O)--;
--CH(OR.sup.6)--;
--CHR.sup.6 --;
--CHR.sup.6 CHR.sup.6 --;
--CR.sup.6 .dbd.CR.sup.6 --;
--C.tbd.C--;
--CHR.sup.6 O--;
--OCHR.sup.6 --;
--CHR.sup.6 S(O).sub.n --;
--S(O).sub.n CHR.sup.6 --;
--CHR.sup.6 O---N.dbd.C(R.sup.7)--;
--(R.sup.7)C.dbd.N--OCH(R.sup.6)--;
--C(R.sup.7).dbd.N--O--;
--O--N.dbd.C(R.sup.7)--;
--CHR.sup.6 OC(.dbd.O)N(R.sup.15)--;
or a direct bond;
and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the phenyl ring and the moiety on the right side of the linkage is bonded to Z;
each R.sup.6 is independently H or C.sub.1 -C.sub.3 alkyl;
R.sup.7 is H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 alkylsulfmyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
C.sub.1 -C.sub.6 haloalkylthio;
C.sub.1 -C.sub.6 haloalkylsulfinyl;
C.sub.1 -C.sub.6 haloalkylsulfonyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.2 -C.sub.4 alkylcarbonyl;
C.sub.2 -C.sub.4 alkoxycarbonyl;
halogen;
cyano;
or morpholinyl;
Z is a ring system selected from:
##STR127## where the point of attachment with Y is selected from any available position on the entire multicyclic ring system, each multicyclic ring system substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ;
each Q is independently selected from the group --CHR.sup.13 --, --NR.sup.13 --, --O--, and --S(O).sub.p --;
R.sup.8 is H;
1-2 halogen;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 haloalkylthio;
C.sub.1 -C.sub.6 alkylsulfinyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.3 -C.sub.6 alkenyloxy;
CO.sub.2 (C.sub.1 -C.sub.6 alkyl);
NH(C.sub.1 -C.sub.6 alkyl);
N(C.sub.1 -C.sub.6 alkyl).sub.2 ;
cyano;
nitro;
SiR.sup.19 R.sup.20 R.sup.21 ;
or GeR.sup.19 R.sup.20 R.sup.21 ;
R.sup.9 is H;
1-2 halogen;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 haloalkylthio;
C.sub.1 -C.sub.6 alkylsulfinyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.3 -C.sub.6 alkenyloxy;
CO.sub.2 (C.sub.1 -C.sub.6 alkyl);
NH(C.sub.1 -C.sub.6 alkyl);
N(C.sub.1 -C.sub.6 alkyl).sub.2 ;
--C(R.sup.18).dbd.NOR.sup.17 ;
cyano;
nitro;
SF.sub.5 ;
SiR.sup.22 R.sup.23 R.sup.24 ;
or GeR.sup.22 R.sup.23 R.sup.24 ;
or R.sup.9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ;
each R.sup.10 is independently halogen;
C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 haloalkyl;
C.sub.1 -C.sub.4 alkoxy;
nitro;
or cyano;
or
when R.sup.9 and an R.sup.10 are attached to adjacent atoms on Z, R.sup.9 and said adjacently attached R.sup.10 can be taken together as --OCH.sub.2 O-- or --OCH.sub.2 CH.sub.2 O--;
each CH.sub.2 group of said taken together R.sup.9 and R.sup.10 optionally substituted with 1-2 halogen;
or
when Y and an R.sup.10 are attached to adjacent atoms on Z and Y is --CHR.sup.6 O--N.dbd.C(R.sup.7)-- or --O--N.dbd.C(R.sup.7)--, R.sup.7 and said adjacently attached R.sup.10 can be taken together as --(CH.sub.2).sub.r --J-- such that J is attached to Z;
J is --CH.sub.2 --;
--CH.sub.2 CH.sub.2 --;
--OCH.sub.2 --;
--CH.sub.2 O--;
--SCH.sub.2 --;
--CH.sub.2 S--;
--N(R.sup.16)CH.sub.2 --;
or --CH.sub.2 N(R.sup.16)--;
each CH.sub.2 group of said J optionally substituted with 1 to 2 CH.sub.3 ;
R.sup.11 and R.sup.12 are each independently halogen;
C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 haloalkyl;
C.sub.1 -C.sub.4 alkoxy;
C.sub.1 -C.sub.4 haloalkoxy;
nitro;
cyano;
Si(R.sup.25).sub.3 ;
or Ge(R.sup.25).sub.3 ;
each R.sup.13 is independently H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano;
R.sup.15, R.sup.16, R.sup.17, and R.sup.18 are each independently H;
C.sub.1 -C.sub.3 alkyl;
or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano;
R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 are each independently C.sub.1 -C.sub.6 alkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.1 -C.sub.4 alkoxy;
or phenyl;
each R.sup.25 is independently C.sub.1 -C.sub.4 alkyl;
m, n and p are each independently 0, 1 or 2;
and
r is 0 or 1.

192 more elements

A compound selected from Formula I, N-oxides and agriculturally-suitable salts thereof, ##STR128## wherein:

W is O or S;
X is OR.sup.1 ;
S(O).sub.m R.sup.1 ;
or halogen;
R.sup.1 is H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.2 -C.sub.4 alkylcarbonyl;
or C.sub.2 -C.sub.4 alkoxycarbonyl;
R.sup.2 is H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.2 -C.sub.4 alkylcarbonyl;
or C.sub.2 -C.sub.4 alkoxycarbonyl;
R.sup.3 and R.sup.4 are each independently H;
halogen;
cyano;
nitro;
hydroxy;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.2 -C.sub.6 alkenyloxy;
C.sub.2 -C.sub.6 alkynyloxy;
or phenyl substituted with R.sup.8 and optionally substituted with one or more R.sup.10 ;
Y is --O--;
--S(O).sub.n --;
--NR.sup.6 --;
--C(.dbd.O)--;
--CH(OR.sup.6)--;
--CHR.sup.6 --;
--CHR.sup.6 CHR.sup.6 --;
--CR.sup.6 .dbd.CR.sup.6 --;
--C.tbd.C--;
--CHR.sup.6 O--;
--OCHR.sup.6 --;
--CHR.sup.6 S(O).sub.n --;
--S(O).sub.n CHR.sup.6 --;
--CHR.sup.6 O--N.dbd.C(R.sup.7)--;
--(R.sup.7)C.dbd.N--OCH(R.sup.6)--;
--C(R.sup.7).dbd.N--O--;
--O--N.dbd.C(R.sup.7)--;
--CHR.sup.6 OC(.dbd.O)N(R.sup.15)--;
or a direct bond;
and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the phenyl ring and the moiety on the right side of the linkage is bonded to Z;
each R.sup.6 is independently H or C.sub.1 -C.sub.3 alkyl;
R.sup.7 is H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 alkylsulfinyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
C.sub.1 -C.sub.6 haloalkylthio;
C.sub.1 -C.sub.6 haloalkylsulfinyl;
C.sub.1 -C.sub.6 haloalkylsulfonyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.2 -C.sub.4 alkylcarbonyl;
C.sub.2 -C.sub.4 alkoxycarbonyl;
halogen;
cyano;
or morpholinyl;
Z is a ring system selected from:
##STR129## where the point of attachment with Y is selected from any available position on the entire multicyclic ring system, each multicyclic ring system substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ;
each Q is independently selected from the group --CHR.sup.13 --, --NR.sup.13 --, --O--, and --S(O).sub.p --;
R.sup.8 is H;
1-2 halogen;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 haloalkylthio;
C.sub.1 -C.sub.6 alkylsulfinyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.3 -C.sub.6 alkenyloxy;
CO.sub.2 (C.sub.1 -C.sub.6 alkyl);
NH(C.sub.1 -C.sub.6 alkyl);
N(C.sub.1 -C.sub.6 alkyl).sub.2 ;
cyano;
nitro;
SiR.sup.19 R.sup.20 R.sup.21 ;
or GeR.sup.19 R.sup.20 R.sup.21 ;
R.sup.9 is H;
1-2 halogen;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 haloalkylthio;
C.sub.1 -C.sub.6 alkylsulfinyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.3 -C.sub.6 alkenyloxy;
CO.sub.2 (C.sub.1 -C.sub.6 alkyl);
NH(C.sub.1 -C.sub.6 alkyl);
N(C.sub.1 -C.sub.6 alkyl).sub.2 ;
--C(R.sup.18).dbd.NOR.sup.17 ;
cyano;
nitro;
SiR.sup.22 R.sup.23 R.sup.24 ;
or GeR.sup.22 R.sup.23 R.sup.24 ;
or R.sup.9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ;
each R.sup.10 is independently halogen;
C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 haloalkyl;
C.sub.1 -C.sub.4 alkoxy;
nitro;
or cyano;
or
when R.sup.9 and an R.sup.10 are attached to adjacent atoms on Z, R.sup.9 and said adjacently attached R.sup.10 can be taken together as --OCH.sub.2 O-- or --OCH.sub.2 CH.sub.2 O--;
each CH.sub.2 group of said taken together R.sup.9 and R.sup.10 optionally substituted with 1-2 halogen;
or
when Y and an R.sup.10 are attached to adjacent atoms on Z and Y is --CHR.sup.6 O--N.dbd.C(R.sup.7)-- or --O--N.dbd.C(R.sup.7)--, R.sup.7 and said adjacently attached R.sup.10 can be taken together as --(CH.sub.2).sub.r --J-- such that J is attached to Z;
J is --CH.sub.2 --;
--CH.sub.2 CH.sub.2 --;
--OCH.sub.2 --;
--CH.sub.2 O--;
--SCH.sub.2 --;
--CH.sub.2 S--;
--N(R.sup.16)CH.sub.2 --;
or --CH.sub.2 N(R.sup.16)--;
each CH.sub.2 group of said J optionally substituted with 1 to 2 CH.sub.3 ;
R.sup.11 and R.sup.12 are each independently halogen;
C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 haloalkyl;
C.sub.1 -C.sub.4 alkoxy;
C.sub.1 -C.sub.4 haloalkoxy;
nitro;
cyano;
Si(R.sup.25).sub.3 ;
or Ge(.sup.25).sub.3 ;
each R.sup.13 is independently H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano;
R.sup.15, R.sup.16, R.sup.17, and R.sup.18 are each independently H;
C.sub.1 -C.sub.3 alkyl;
or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano;
R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 are each independently C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.4 alkoxy;
or phenyl;
each R.sup.25 is independently C.sub.1 -C.sub.4 alkyl;
m, n and p are each independently 0, 1 or 2;
and
r is 0 or 1.

171 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/894,539Filed 21 Aug 1997 · continuation in part
Priority: 24 Feb 1995
Granted: 5 Oct 1999
Term ends: Not estimatedThe source records don’t support an estimate.

Classification13 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A01N 43/653
Triazoles; Hydrogenated triazoles: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
A01N 43/80
Having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms: five-membered rings with one nitrogen atom and either one oxygen…
C07D 249/12
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,…:…

Family

Serial393,743Parent of this continuation-in-part · filed 24 Feb 1995
US 5,962,436 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Cyclic amides, including triazole containing cyclic amides, their N-oxides, agriculturally-suitable salts and compositions, and their methods of use as fungicides.

A compound selected from Formula I, N-oxides and agriculturally-suitable salts thereof, ##STR126## wherein:

W is O;
S;
NH;
N(C.sub.1 -C.sub.6 alkyl);
or NO(C.sub.1 -C.sub.6 alkyl);
X is OR.sup.1 ;
S(O).sub.m R.sup.1 ;
or halogen;
R.sup.1 is H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.2 -C.sub.4 alkylcarbonyl;
or C.sub.2 -C.sub.4 alkoxycarbonyl;
R.sup.2 is H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.2 -C.sub.4 alkylcarbonyl;
C.sub.2 -C.sub.4 alkoxycarbonyl;
hydroxy;
C.sub.1 -C.sub.2 alkoxy;
or acetyloxy;
R.sup.3 and R.sup.4 are each independently H;
halogen;
cyano;
nitro;
hydroxy;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.2 -C.sub.6 alkenyloxy;
C.sub.2 -C.sub.6 alkynyloxy;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 alkylsulfinyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
formyl;
C.sub.2 -C.sub.6 alkylcarbonyl;
C.sub.2 -C.sub.6 alkoxycarbonyl;
NH.sub.2 C(O);
(C.sub.1 -C.sub.4 alkyl)NHC(O);
(C.sub.1 -C.sub.4 alkyl).sub.2 NC(O);
Si(R.sup.25).sub.3 ;
Ge(R.sup.25).sub.3 ;
(R.sup.25).sub.3 Si--C.tbd.C--;
or phenyl, phenylethynyl, benzoyl, or phenylsulfonyl each substituted with R.sup.8 and optionally substituted with one or more R.sup.10 ;
Y is --O--;
--S(O).sub.n --;
--NR.sup.6 --;
--C(.dbd.O)--;
--CH(OR.sup.6)--;
--CHR.sup.6 --;
--CHR.sup.6 CHR.sup.6 --;
--CR.sup.6 .dbd.CR.sup.6 --;
--C.tbd.C--;
--CHR.sup.6 O--;
--OCHR.sup.6 --;
--CHR.sup.6 S(O).sub.n --;
--S(O).sub.n CHR.sup.6 --;
--CHR.sup.6 O---N.dbd.C(R.sup.7)--;
--(R.sup.7)C.dbd.N--OCH(R.sup.6)--;
--C(R.sup.7).dbd.N--O--;
--O--N.dbd.C(R.sup.7)--;
--CHR.sup.6 OC(.dbd.O)N(R.sup.15)--;
or a direct bond;
and the directionality of the Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the phenyl ring and the moiety on the right side of the linkage is bonded to Z;
each R.sup.6 is independently H or C.sub.1 -C.sub.3 alkyl;
R.sup.7 is H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 alkylsulfmyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
C.sub.1 -C.sub.6 haloalkylthio;
C.sub.1 -C.sub.6 haloalkylsulfinyl;
C.sub.1 -C.sub.6 haloalkylsulfonyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.2 -C.sub.6 haloalkynyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.2 -C.sub.4 alkylcarbonyl;
C.sub.2 -C.sub.4 alkoxycarbonyl;
halogen;
cyano;
or morpholinyl;
Z is a ring system selected from:
##STR127## where the point of attachment with Y is selected from any available position on the entire multicyclic ring system, each multicyclic ring system substituted with R.sup.9 and optionally substituted with one or more R.sup.10 ;
each Q is independently selected from the group --CHR.sup.13 --, --NR.sup.13 --, --O--, and --S(O).sub.p --;
R.sup.8 is H;
1-2 halogen;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 haloalkylthio;
C.sub.1 -C.sub.6 alkylsulfinyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.3 -C.sub.6 alkenyloxy;
CO.sub.2 (C.sub.1 -C.sub.6 alkyl);
NH(C.sub.1 -C.sub.6 alkyl);
N(C.sub.1 -C.sub.6 alkyl).sub.2 ;
cyano;
nitro;
SiR.sup.19 R.sup.20 R.sup.21 ;
or GeR.sup.19 R.sup.20 R.sup.21 ;
R.sup.9 is H;
1-2 halogen;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
C.sub.1 -C.sub.6 alkoxy;
C.sub.1 -C.sub.6 haloalkoxy;
C.sub.2 -C.sub.6 alkenyl;
C.sub.2 -C.sub.6 haloalkenyl;
C.sub.2 -C.sub.6 alkynyl;
C.sub.1 -C.sub.6 alkylthio;
C.sub.1 -C.sub.6 haloalkylthio;
C.sub.1 -C.sub.6 alkylsulfinyl;
C.sub.1 -C.sub.6 alkylsulfonyl;
C.sub.3 -C.sub.6 cycloalkyl;
C.sub.3 -C.sub.6 alkenyloxy;
CO.sub.2 (C.sub.1 -C.sub.6 alkyl);
NH(C.sub.1 -C.sub.6 alkyl);
N(C.sub.1 -C.sub.6 alkyl).sub.2 ;
--C(R.sup.18).dbd.NOR.sup.17 ;
cyano;
nitro;
SF.sub.5 ;
SiR.sup.22 R.sup.23 R.sup.24 ;
or GeR.sup.22 R.sup.23 R.sup.24 ;
or R.sup.9 is phenyl, benzyl, benzoyl, phenoxy, pyridinyl, pyridinyloxy, thienyl, thienyloxy, furanyl, pyrimidinyl, or pyrimidinyloxy each optionally substituted with one of R.sup.11, R.sup.12, or both R.sup.11 and R.sup.12 ;
each R.sup.10 is independently halogen;
C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 haloalkyl;
C.sub.1 -C.sub.4 alkoxy;
nitro;
or cyano;
or
when R.sup.9 and an R.sup.10 are attached to adjacent atoms on Z, R.sup.9 and said adjacently attached R.sup.10 can be taken together as --OCH.sub.2 O-- or --OCH.sub.2 CH.sub.2 O--;
each CH.sub.2 group of said taken together R.sup.9 and R.sup.10 optionally substituted with 1-2 halogen;
or
when Y and an R.sup.10 are attached to adjacent atoms on Z and Y is --CHR.sup.6 O--N.dbd.C(R.sup.7)-- or --O--N.dbd.C(R.sup.7)--, R.sup.7 and said adjacently attached R.sup.10 can be taken together as --(CH.sub.2).sub.r --J-- such that J is attached to Z;
J is --CH.sub.2 --;
--CH.sub.2 CH.sub.2 --;
--OCH.sub.2 --;
--CH.sub.2 O--;
--SCH.sub.2 --;
--CH.sub.2 S--;
--N(R.sup.16)CH.sub.2 --;
or --CH.sub.2 N(R.sup.16)--;
each CH.sub.2 group of said J optionally substituted with 1 to 2 CH.sub.3 ;
R.sup.11 and R.sup.12 are each independently halogen;
C.sub.1 -C.sub.4 alkyl;
C.sub.1 -C.sub.4 haloalkyl;
C.sub.1 -C.sub.4 alkoxy;
C.sub.1 -C.sub.4 haloalkoxy;
nitro;
cyano;
Si(R.sup.25).sub.3 ;
or Ge(R.sup.25).sub.3 ;
each R.sup.13 is independently H;
C.sub.1 -C.sub.6 alkyl;
C.sub.1 -C.sub.6 haloalkyl;
or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano;
R.sup.15, R.sup.16, R.sup.17, and R.sup.18 are each independently H;
C.sub.1 -C.sub.3 alkyl;
or phenyl optionally substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, nitro or cyano;
R.sup.19, R.sup.20, R.sup.21, R.sup.22, R.sup.23, and R.sup.24 are each independently C.sub.1 -C.sub.6 alkyl;
C.sub.2 -C.sub.6 alkenyl;
C.sub.1 -C.sub.4 alkoxy;
or phenyl;
each R.sup.25 is independently C.sub.1 -C.sub.4 alkyl;
m, n and p are each independently 0, 1 or 2;
and
r is 0 or 1.

192 more elements

Facts

Application

08/894,539Filed 21 Aug 1997 · continuation in part

Priority

24 Feb 1995

Granted

5 Oct 1999

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A01N 43/653
Triazoles; Hydrogenated triazoles: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
A01N 43/80
Having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms: five-membered rings with one nitrogen atom and either one oxygen…
C07D 249/12
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,…:…