US 2008/0293573 A1 · Pyrazolyl-substituted heterocycles and their use as phytosanitary products

1-17. (canceled)

18:

A compound of formula (I-2-A) or (I-3-A)
in which
X represents optionally substituted phenyl or hetaryl,
Y represents hydrogen or alkyl,
Z represents alkyl, halogen, hydroxyl, alkoxy, or haloalkoxy;
or represents optionally substituted phenylalkyloxy, hetarylalkyloxy, or cycloalkyl,
A represents hydrogen;
represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, or alkylthioalkyl;
represents saturated or unsaturated, optionally substituted cycloalkyl in which one or more ring atom is optionally replaced by a heteroatom;
or represents optionally halogen-, alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, cyano-, or nitro-substituted aryl, arylalkyl, or hetaryl,
B represents hydrogen, alkyl, or alkoxyalkyl, or
A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle that optionally contains one or more heteroatoms, and
G represents hydrogen (a) or represents one of the groups
in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur,
M represents oxygen or sulphur,
R1 represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, or polyalkoxyalkyl;
represents optionally halogen-, alkyl-, or alkoxy-substituted cycloalkyl that is optionally interrupted by one or more heteroatoms;
or represents optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl, or hetaryloxyalkyl,
R2 represents optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, or polyalkoxyalkyl;
or represents optionally substituted cycloalkyl, phenyl, or benzyl,
R3 represents alkyl, haloalkyl or represents optionally substituted phenyl or benzyl,
R4 and R5 independently of one another represent optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, or cycloalkylthio;
or represent optionally substituted phenyl, benzyl, phenoxy, or phenylthio, and
R6 and R7 independently of one another represent hydrogen;
represent optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, or alkoxyalkyl;
represent optionally substituted phenyl;
or represent optionally substituted benzyl;
or R6 and R7 together with the N atom to which they are attached represent a cycle that is optionally interrupted by oxygen or sulphur.

27 more elements

19:

A compound according to claim 18 in which
X represents optionally halogen-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C4-haloalkyl-, C1-C4-haloalkoxy-, nitro-, or cyano-substituted phenyl or 5- or 6-membered hetaryl,
Y represents hydrogen, halogen, or C1-C6-alkyl,
Z represents C1-C6-alkyl, halogen, hydroxyl, C1-C6-alkoxy, or C1-C6-haloalkoxy;
represents optionally C1-C6-alkyl-, C1-C6-alkoxy-, halogen-, C1-C4-haloalkyl-, C1-C6-haloalkoxy-, cyano-, or nitro-substituted phenyl-C1-C2-alkoxy or hetaryl-C1-C2-alkoxy;
or represents optionally C1-C2-alkyl- or halogen-substituted C3-C6-cycloalkyl,
A represents hydrogen;
represents optionally fluorine- or chlorine-substituted C1-C12-alkyl, C3-C8-alkenyl, C1-C10-alkoxy-C1-C8-alkyl, poly-C1-C8-alkoxy-C1-C8-alkyl, or C1-C10-alkylthio-C1-C6-alkyl;
represents optionally fluorine-, chlorine-, C1-C6-alkyl-, or C1-C6-alkoxy-substituted C3-C8-cycloalkyl in which one or two ring members that are not directly adjacent are optionally replaced by oxygen and/or sulphur;
or represents optionally halogen-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, cyano-, or nitro-substituted C6- or C10-aryl, hetaryl having 5 or 6 ring atoms, or C6- or C10-aryl-C1-C6-alkyl,
B represents hydrogen, C1-C12-alkyl or C1-C8-alkoxy-C1-C6-alkyl, or
A, B, and the carbon atom to which they are attached represent saturated C3-C10-cycloalkyl or unsaturated C5-C10-cycloalkyl in which one ring member is optionally replaced by oxygen or sulphur and that is optionally mono- or disubstituted by C1-C8-alkyl, C3-C10-cycloalkyl, C1-C8-haloalkyl, C1-C8-alkoxy, C1-C8-alkylthio, halogen, or phenyl, or
A, B, and the carbon atom to which they are attached represent C5-C6-cycloalkyl that is substituted by an alkylenediyl group that optionally contains one or two oxygen and/or sulphur atoms that are not directly adjacent or by an alkylene-dioxyl or an alkylenedithioyl group which, together with the carbon atom to which it is attached, forms a further five- to eight-membered ring that is optionally substituted by C1-C4-alkyl, or
A, B, and the carbon atom to which they are attached represent C3-C8-cycloalkyl or C5-C8-cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent optionally C1-C6-alkyl-, C1-C6-alkoxy-, or halogen-substituted C2-C6-alkanediyl, C2-C6-alkenediyl, or C4-C6-alkane-dienediyl in which one methylene group is optionally replaced by oxygen or sulphur, and
G represents hydrogen (a) or represents one of the groups
in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur,
M represents oxygen or sulphur,
R1 represents optionally halogen-substituted C1-C20-alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C1-C8-alkyl, C1-C8-alkylthio-C1-C8-alkyl, or poly-C1-C8-alkoxy-C1-C8-alkyl;
or represents optionally halogen-, C1-C6-alkyl-, or C1-C6-alkoxy-substituted C3-C8-cycloalkyl in which one or more ring members that are not directly adjacent are optionally replaced by oxygen and/or sulphur;
represents optionally halogen-, cyano-, nitro-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-haloalkyl-, C1-C6-haloalkoxy-, C1-C6-alkylthio-, or C1-C6-alkylsulphonyl-substituted phenyl;
represents optionally halogen-, nitro-, cyano-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-haloalkyl-, or C1-C6-haloalkoxy-substituted phenyl-C1-C6-alkyl;
represents optionally halogen-, C1-C6-alkyl-, C1-C2-haloalkyl-, or C1-C4-alkoxy-substituted 5- or 6-membered hetaryl;
represents optionally halogen- or C1-C6-alkyl-substituted phenoxy-C1-C6-alkyl;
or represents optionally halogen-, amino-, or C1-C6-alkyl-substituted 5- or 6-membered hetaryloxy-C1-C6-alkyl,
R2 represents optionally halogen-substituted C1-C20-alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C2-C8-alkyl, or poly-C1-C8-alkoxy-C2-C8-alkyl;
represents optionally halogen-, C1-C6-alkyl-, or C1-C6-alkoxy-substituted C3-C8-cycloalkyl in which one ring atom is optionally replaced by oxygen;
or represents optionally halogen-, cyano-, nitro-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-haloalkyl-, or C1-C6-haloalkoxy-substituted phenyl or benzyl,
R3 represents optionally halogen-substituted C1-C8-alkyl;
or represents optionally halogen-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C4-haloalkyl-, C1-C4-haloalkoxy-, cyano-, or nitro-substituted phenyl or benzyl,
R4 and R5 independently of one another represent optionally halogen-substituted C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino, di(C1-C8-alkyl)amino, C1-C8-alkylthio, C2-C8-alkenylthio, or C3-C7-cycloalkyl-thio;
or represent optionally halogen-, nitro-, cyano-, C1-C4-alkoxy-, C1-C4-haloalkoxy-, C1-C4-alkylthio-, C1-C4-haloalkylthio-, C1-C4-alkyl-, or C1-C4-haloalkyl-substituted phenyl, phenoxy or phenylthio, and
R6 and R7 independently of one another represent hydrogen;
represent optionally halogen-substituted C1-C8-alkyl, C3-C8-cycloalkyl, C1-C8-alkoxy, C3-C8-alkenyl, or C1-C8-alkoxy-C1-C8-alkyl;
represent optionally halogen-, C1-C8-haloalkyl-, C1-C8-alkyl-, or C1-C8-alkoxy-substituted phenyl;
or represent optionally halogen-, C1-C8-alkyl-, C1-C8-haloalkyl-, or C1-C8-alkoxy-substituted benzyl;
or R6 and R7 together represent an optionally C1-C4-alkyl-substituted C3-C6-alkylene radical in which one carbon atom is optionally replaced by oxygen or sulphur.

35 more elements

20:

A compound according to claim 18 in which
X represents phenyl, pyridyl, pyrimidyl, or thiazolyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-haloalkyl, C1-C2-haloalkoxy, nitro, or cyano,
Y represents hydrogen, chlorine, bromine, or C1-C4-alkyl,
Z represents C1-C4-alkyl, chlorine, bromine, C1-C4-alkoxy, or C1-C4-haloalkoxy;
or represents benzyloxy or hetaryloxy having 5 or 6 ring atoms, each of which radicals is optionally mono- or disubstituted by C1-C4-alkyl, C1-C4-alkoxy, fluorine, chlorine, bromine, C1-C2-haloalkyl, C1-C2-haloalkoxy, cyano, or nitro,
A represents hydrogen;
represents optionally fluorine-substituted C1-C10-alkyl, or C1-C8-alkoxy-C1-C6-alkyl;
represents optionally fluorine-, chlorine-, C1-C4-alkyl-, or C1-C4-alkoxy-substituted C3-C7-cycloalkyl in which one ring member is optionally replaced by oxygen or sulphur;
or represents phenyl or phenyl-C1-C2-alkyl, each of which is optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, cyano, nitro, or C1-C4-haloalkoxy,
B represents hydrogen or C1-C10-alkyl, or
A, B, and the carbon atom to which they are attached represent saturated C3-C7-cycloalkyl or unsaturated C5-C7-cycloalkyl in which one ring member is optionally replaced by oxygen or sulphur and that is optionally mono- or disubstituted by C1-C6-alkyl, C5-C8-cycloalkyl, C1-C3-haloalkyl, C1-C6-alkoxy, fluorine, chlorine, or phenyl, or
A, B, and the carbon atom to which they are attached represent C5-C6-cycloalkyl that is substituted by an alkylenediyl group that optionally contains one or two oxygen or sulphur atoms that are not directly adjacent or by an alkylenedioxyl or by an alkylenedithiolyl group which, together with the carbon atom to which it is attached, forms a further five- or six-membered ring that is optionally substituted by C1-C3-alkyl, or
A, B, and the carbon atom to which they are attached represent C5-C6-cycloalkyl or C5-C6-cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent C2-C4-alkanediyl or C2-C4-alkenediyl in which one methylene group is optionally replaced by oxygen or sulphur, each of which radicals is optionally substituted by C1-C5-alkyl, C1-C5-alkoxy, fluorine, chlorine, or bromine, or represent butadienediyl, and
G represents hydrogen (a) or represents one of the groups
in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur,
M represents oxygen or sulphur,
R1 represents optionally fluorine- or chlorine-substituted C1-C16-alkyl, C2-C16-alkenyl, C1-C6-alkoxy-C1-C4-alkyl, or C1-C6-alkylthio-C1-C4-alkyl;
represents optionally fluorine-, chlorine-, C1-C5-alkyl-, or C1-C5-alkoxy-substituted C3-C7-cycloalkyl in which one or two ring members that are not directly adjacent are optionally replaced by oxygen and/or sulphur;
represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C3-haloalkyl-, C1-C3-halo-alkoxy-, C1-C4-alkylthio-, or C1-C4-alkylsulphonyl-substituted phenyl;
represents optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C3-haloalkyl-, or C1-C3-haloalkoxy-substituted phenyl-C1-C4-alkyl;
or represents optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, trifluoromethyl-, or C1-C2-alkoxy-substituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl, or thienyl,
R2 represents optionally fluorine-substituted C1-C16-alkyl, C2-C16-alkenyl, or C1-C6-alkoxy-C2-C6-alkyl;
represents optionally fluorine-, chlorine-, C1-C4-alkyl-. or C1-C4-alkoxy-substituted C3-C7-cycloalkyl;
or represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, C1-C3-alkoxy-, C1-C2-haloalkyl-, or C1-C2-haloalkoxy-substituted phenyl or benzyl,
R3 represents optionally fluorine-substituted C1-C6-alkyl;
or represents optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C3-haloalkyl-, C1-C3-haloalkoxy-, cyano-, or nitro-substituted phenyl,
R4 represents C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylthio, C3-C4-alkenylthio, or C3-C6-cycloalkyl-thio;
or represents optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C1-C3-alkoxy-, C1-C3-haloalkoxy-, C1-C3-alkylthio-, C1-C3-haloalkylthio-, C1-C3-alkyl-, or C1-C3-haloalkyl-substituted phenyl, phenoxy, or phenylthio,
R5 represents C1-C6-alkoxy or C1-C6-alkylthio,
R6 represents C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyl, or C1-C6-alkoxy-C1-C6-alkyl;
represents optionally fluorine-, chlorine-, bromine-, C1-C3-haloalkyl-, C1-C4-alkyl-, or C1-C4-alkoxy-substituted phenyl;
represents optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C3-haloalkyl-, or C1-C4-alkoxy-substituted benzyl, and
R7 represents hydrogen, C1-C6-alkyl, C3-C6-alkenyl, or
R6 and R7 together represent an optionally methyl- or ethyl-substituted C4-C5-alkylene radical in which one methylene group is optionally replaced by oxygen or sulphur.

33 more elements

21:

A compound according to claim 18 in which
X represents phenyl that is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, isopropyl, tert-butyl, trifluoromethoxy, methoxy, ethoxy, isopropoxy, tert-butoxy, cyano, or nitro,
Y represents hydrogen, methyl, or ethyl,
Z represents methyl, ethyl, propyl, isopropyl, chlorine, methoxy, ethoxy, propoxy, isopropoxy, difluoromethoxy, or trifluoroethoxy,
A represents hydrogen;
represents optionally fluorine-substituted C1-C8-alkyl, or C1-C6-alkoxy-C1-C4-alkyl;
represents optionally fluorine-, methyl-, ethyl-, or methoxy-substituted C3-C6-cycloalkyl in which one ring member is optionally replaced by oxygen or sulphur;
or represents phenyl or benzyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyano, or nitro,
B represents hydrogen or C1-C6-alkyl, or
A, B, and the carbon atom to which they are attached represent saturated C3-C6-cycloalkyl in which one ring member is optionally replaced by oxygen or sulphur and that is optionally monosubstituted by methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, fluorine, or chlorine, or
A, B, and the carbon atom to which they are attached represent C6-cycloalkyl that is substituted by an alkylenedioxyl group that is optionally mono- or disubstituted by methyl or ethyl and which, together with the carbon atom to which it is attached, forms a further five- or six-membered ring, or
A, B, and the carbon atom to which they are attached represent C5-C6-cycloalkyl or C5-C6-cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent C2-C4-alkanediyl or C2-C4-alkenediyl in which one methylene group is optionally replaced by oxygen or sulphur, or represent butadienediyl, and
G represents hydrogen (a) or represents one of the groups
in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur,
M represents oxygen or sulphur,
R1 represents optionally fluorine- or chlorine-substituted C1-C14-alkyl, C2-C14-alkenyl, C1-C4-alkoxy-C1-C2-alkyl, or C1-C4-alkylthio-C1-C2-alkyl;
represents C3-C6-cycloalkyl that is optionally mono- or disubstituted by fluorine, chlorine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, or ethoxy and in which one or two ring members that are not directly adjacent are optionally replaced by oxygen and/or sulphur;
represents phenyl that is optionally mono- or disubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, tert-butyl, methoxy, ethoxy, i-propoxy, tert-butoxy, trifluoromethyl, or trifluoromethoxy;
or represents furanyl, thienyl, or pyridyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, or ethyl;
R2 represents C1-C14-alkyl, C2-C14-alkenyl, or C1-C4-alkoxy-C2-C6-alkyl, each of which is optionally mono- to trisubstituted by fluorine;
represents C3-C6-cycloalkyl that is optionally mono- or disubstituted by fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, or methoxy;
or represents phenyl or benzyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl, or trifluoromethoxy,
R3 represents methyl, ethyl, or n-propyl, each of which is optionally mono- to trisubstituted by fluorine;
or represents phenyl that is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano, or nitro,
R4 represents C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylamino, di(C1-C4-alkyl)amino, or C1-C4-alkylthio;
or represents phenyl, phenoxy, or phenylthio, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, nitro, cyano, C1-C2-alkoxy, C1-C2-fluoroalkoxy, C1-C2-alkylthio, C1-C2-fluoroalkylthio, or C1-C3-alkyl,
R5 represents methoxy, ethoxy, methylthio, or ethylthio,
R6 represents C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C3-C4-alkenyl, C1-C4-alkoxy-C1-C4-alkyl;
represents phenyl that is optionally mono- or disubstituted by fluorine, chlorine, bromine, trifluoromethyl, methyl, or methoxy;
represents benzyl that is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, or methoxy, and
R7 represents hydrogen, methyl, ethyl, propyl, or allyl, or
R6 and R7 together represent a C5-C6-alkylene radical in which one methylene group is optionally replaced by oxygen or sulphur.

31 more elements

22:

A compound of formula (I-2-A) according to claim 18
in which
X represents phenyl that is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, or trifluoromethoxy,
Y represents hydrogen or methyl,
Z represents methyl, ethyl, or propyl, and
A represents hydrogen or C1-C6-alkyl,
B represents hydrogen or C1-C6-alkyl, or
A, B, and the carbon atom to which they are attached represent saturated C5-C6-cycloalkyl in which one ring member is optionally replaced by oxygen or sulphur and that is optionally monosubstituted by methyl, ethyl, propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, or isobutoxy, or
A, B, and the carbon atom to which they are attached represent C5-C6-cycloalkyl or C5-C6-cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent butadienyl, and
G represents hydrogen (a) or represents one of the groups
in which
L represents oxygen,
M represents oxygen or sulphur,
R1 represents C1-C6-alkyl, C2-C6-alkenyl, C1-C2-alkoxy-C1-C2-alkyl, or C1-C2-alkylthio-C1-C2-alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine;
or represents C3-C6-cycloalkyl that is optionally monosubstituted by fluorine, chlorine, methyl, ethyl, or methoxy and in which one ring member is optionally replaced by oxygen or sulphur;
represents phenyl which is optionally mono-substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, tert-butyl, methoxy, ethoxy, i-propoxy, tert-butoxy, trifluoromethyl, or trifluoromethoxy;
or represents thienyl or pyridyl, each of which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, or ethyl, and
R2 represents C1-C6-alkyl, C2-C6-alkenyl, or C1-C4-alkoxy-C2-C3-alkyl, each of which is optionally mono- to trisubstituted by fluorine;
represents cyclopentyl or cyclohexyl;
or represents phenyl or benzyl, each of which is optionally monosubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl, or trifluoromethoxy.

17 more elements

23:

A process for preparing a compound according to claim 18 comprising
(B) for substituted 3-pyrazolyl-4-hydroxy-Δ3-dihydrofuranone derivatives of formula (I-2-A-a)
in which A, B, X, Y, and Z are as defined in claim 18,
intramolecularly condensing a carboxylic acid ester of formula (III-A)
in which
A, B, X, Y, and Z are as defined in claim 18, and
R8 represents alkyl,
in the presence of a diluent and in the presence of a base,
(C) for substituted 3-thiazolyl-4-hydroxy-Δ3-dihydrothiophen-2-one derivatives of formula (I-3-A-a)
in which A, B, X, Y, and Z are as defined in claim 18,
intramolecularly cyclizing a β-ketocarboxylic acid ester of formula (IV-A)
in which
A, B, X, Y, and Z are as defined in claim 18,
R8 represents alkyl, and
W1 represents hydrogen, halogen, alkyl, or alkoxy,
optionally in the presence of a diluent and in the presence of an acid,
(D) for compounds of formula (I-2-A-b) or (I-3-A-b)
in which A, B, D, R1, X, Y, and Z are as defined in claim 18,
reacting a compound of formula (I-2-A-a) or (I-3-A-a
(α) with an acid halide of formula (V)
in which
R1 is as defined in claim 18, and
Hal represents halogen,
or
(β) with a carboxylic anhydride of formula (VI)
R1—CO—O—CO—R1 (VI)
in which
R1 is as defined in claim 18,
optionally in the presence of a diluent and optionally in the presence of an acid binder,
(E) for compounds of formula (I-2-A-c) or (I-3-A-c)
in which
A, B, D, R2, M, X, Y, and Z are as defined in claim 18, and
L represents oxygen,
reacting a compound of formula (I-2-A-a) or (I-3-A-a) with a chloroformic acid ester or chloroformic acid thioester of formula (VII)
R2-M-CO—Cl (VII)
in which R2 and M are as defined in claim 18,
optionally in the presence of a diluent and optionally in the presence of an acid binder;
(F) for compounds of formula (I-2-A-c) or (I-3-A-c)
in which
A, B, D, R2, M, X, Y, and Z are as defined in claim 18, and
L represents sulphur,
reacting a compound of formula (I-2-A-a) or (I-3-A-a) with a chloromonothioformic acid ester or chlorodithioformic acid ester of formula (VIII)
in which R2 and M are as defined in claim 18,
optionally in the presence of a diluent and optionally in the presence of an acid binder;
(G) for compounds of formula (I-2-A-d) or (I-3-A-d)
in which A, B, D, R3, X, Y and Z are as defined in claim 18,
reacting a compound of formula (I-2-A-a) or (I-3-A-a) with a sulphonyl chloride of formula (IX)
R3—SO2—Cl (IX)
in which R3 is as defined in claim 18,
optionally in the presence of a diluent and optionally in the presence of an acid binder,
(H) for compounds of formula (I-2-A-e) or (I-3-A-e)
in which A, B, D, L, R4, R5, X, Y, and Z are as defined in claim 18, reacting a compound of formula (I-2-A-a) or (I-3-A-a) with a phosphorus compound of formula (X)
in which
L, R4, and R5 are as defined in claim 18, and
Hal represents halogen,
optionally in the presence of a diluent and optionally in the presence of an acid binder,
(I) for compounds of formula (I-2-A-f) or (I-3-A-f)
in which A, B, D, E, X, Y, and Z are as defined in claim 18,
reacting a compound of formula (I-2-A-a) or (I-3-A-a) with a metal compound of formula (XI)
Me(OR10)t (XI)
in which
Me represents a mono- or divalent metal,
R10 represents hydrogen or alkyl, and
t represents the number 1 or 2, or
an amine of formula (XII)
in which R10, R11, and R12 independently of one another represent hydrogen or alkyl,
optionally in the presence of a diluent, and
(J) for compounds of formula (I-2-A-g) or (I-3-A-g)
in which A, B, D, L, R6, R7, X, Y and Z are as defined in claim 18,
reacting a compound of formula (I-2-A-a) or (I-3-A-a)
(α) with an isocyanate or isothiocyanate of formula (XIII)
R6—N═C=L (XIII)
in which R6 and L are as defined in claim 18,
optionally in the presence of a diluent and optionally in the presence of a catalyst, or
(β) with a carbamoyl chloride or thiocarbamoyl chloride of formula (XIV)
in which L, R6 and R7 are as defined in claim 18,
optionally in the presence of a diluent and optionally in the presence of an acid binder.

74 more elements

Pyrazolyl-substituted heterocycles and their use as phytosanitary products

Life of this patent

Abstract

Claims16

Pyrazolyl-substituted heterocycles and their use as phytosanitary products

Life of this patent

Abstract

Claims16