US 9,000,189 B2Granted

Biphenyl-substituted spirocyclic ketoenols

AssigneeBayer CropScience AG

InventorsThomas Bretschneider, Reiner Fischer, Rolf Pontzen, Christian Arnold, Ulrich Görgens, Olga Malsam, Udo Reckmann, Erich Sanwald, Stefan Lehr, Jan Dittgen, Dieter Feucht, Martin Hills, Christopher Rosinger

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Abstract

The invention relates to novel compounds of the formula (I) in which W, X, Y, Z and CKE have the meanings given above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising, firstly, the compounds of the formula (I) and, secondly, at least one crop plant compatibility-improving compound. The invention further relates to the boosting of the action of crop protection compositions comprising compounds of the formula (I) through the additions of ammonium salts or phosphonium salts and optionally penetrants.

Claims7

Dependent claims

A compound of formula (I)

in which
W represents hydrogen or methyl,
X represents fluorine, chlorine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy,
Y represents hydrogen, methyl, fluorine or chlorine,
Z represents the radical
V1 represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
V2 represents hydrogen, fluorine, chlorine, methyl or methoxy,
CKE represents one of the groups
A, B and the carbon atom to which they are attached represent saturated C6-cycloalkyl in which one ring member is replaced by oxygen at 3 or 4 position,
G represents hydrogen (a) or represents one of the groups
in which
L represents oxygen or sulphur,
M represents oxygen or sulphur and
E represents a metal ion equivalent or an ammonium ion,
R1 represents C1-C6-alkyl, C2-C6-alkenyl, C1-C2-alkoxy-C1-alkyl, C1-C2-alkylthio-C1-alkyl, each of which is optionally monosubstituted by fluorine or chlorine, or represents cyclopropyl or cyclohexyl, each of which is optionally monosubstituted by fluorine, chlorine, methyl or methoxy,
represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
R2 represents C1-C8-alkyl, C2-C6-alkenyl or C1-C4-alkoxy-C2-C3-alkyl, phenyl or benzyl, each of which is optionally monosubstituted by fluorine.

14 more elements

A process for preparing compounds of formula (I) according to claim 1, characterized in that,

(A) in order to obtain a compound of formula (I-1-a)
in which
A, B, W, X, Y and Z are as defined in claim 1,
an N-acylamino acid ester of formula (II)
in which
A, B, W, X, Y and Z are as defined in claim 1,
and
R8 represents alkyl
is condensed intramolecularly in the presence of a diluent and in the presence of a base;
(B) in order to obtain a compound of formula (I-2-a)
in which
A, B, W, X, Y and Z are as defined in claim 1,
a carboxylic ester of the formula (III)
in which
A, B, W, X, Y and Z are as defined in claim 4 and R8 is alkyl,
is condensed intramolecularly in the presence of a diluent and in the presence of a base;
(C) in order to obtain a compound of formula (I-1-a), (I-1-b), (I-1-c), (I-1-f), (I-2-a), (I-2-b), (I-2-c), or (I-2-f) shown below,
in which
A, B, E, L, M, W, X, Y, Z, R1, and R2, are as defined in claim 1,
a corresponding compound of formula (I-1′-a), (I-1′-b), (I-1′-c), (I-1′-f), (I-2′-a), (I-2′-b), (I-2′-c), or (I-2′-f), respectively
in which
A, B, G, W, X and Y are as defined in claim 1, and
Z′ represents chlorine, bromine, or iodine,
is reacted with a boronic acid or a boronic acid derivative of the formula (IV)
in which
R9 represents hydrogen, C1-C6-alkyl or C2-C6-alkanediyl
and
Z is as defined in claim 1,
in the presence of a solvent, a base and a catalyst, wherein the catalyst is a palladium salt or a palladium complex;
(D) in order to obtain a compound of formula (I-1-b) or formula (I-2-b) in which A, B, R1, W, X, Y and Z are as defined in claim 1, a compound of the formula (I-1-a) or (I-2-a) in which A, B, W, X, Y and Z are as defined in claim 1, is in each case reacted
(α) with an acid halide of formula (V)
in which
R1 is as defined in claim 1, and
Hal represents halogen,
or
(β) with a carboxylic anhydride of the formula (VI)
R1—CO—O—CO—R1 (VI)
in which
R1 is as defined in claim 1,
optionally in the presence of a diluent and optionally in the presence of an acid binder;
(E) in order to obtain a compound of formula (I-1-c) or (I-2-c) in which A, B, R2, M, W, X, Y and Z are as defined in claim 1, and L represents oxygen, a compound of the formula (I-1-a) or (I-2-a) in which A, B, W, X, Y and Z are as defined in claim 1, is in each case reacted
with a chloroformic ester or a chloroformic thioester of formula (VII)
R2-M-CO—Cl (VII)
in which
R2 and M are as defined in claim 1,
optionally in the presence of a diluent and optionally in the presence of an acid binder;
(F) in order to obtain a compound of formula (I-1-c) or (I-2-c) in which A, B, R2, M, W, X, Y and Z are as defined in claim 1 and L represents sulphur, a compound of formula (I-1-a) or (I-2-a) in which A, B, W, X, Y and Z are as defined in claim 1, is in each case reacted
with a chloromonothioformic ester or a chlorodithioformic ester of formula (VIII)
in which
M and R2 are as defined in claim 1,
optionally in the presence of a diluent and optionally in the presence of an acid binder;
and
(G) in order to obtain a compound of formula (I-1-f) or (I-2-f) in which A, B, E, W, X, Y and Z are as defined in claim 1, a compound of formula (I-1-a) or (I-2-a) in which A, B, W, X, Y and Z are as defined in claim 1, is in each case reacted
with a metal compound or an amine of formulae (XI) and (XII), respectively,
in which
Me represents a mono- or divalent metal,
t represents the number 1 or 2 and
R10, R11, R12 independently of one another represent hydrogen or alkyl,
optionally in the presence of a diluent.

56 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/517,419Filed 22 Nov 2007
Priority: DE 10 2006 057 0364 Dec 2006
Published: US 2011/0306499 A115 Dec 2011
Granted: 7 Apr 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification26 codes

C07D 209/54
Condensed with one carbocyclic ring: spiro-condensed
A01N 43/12
Five-membered rings: condensed with a carbocyclic ring
A01N 43/38
Five-membered rings: condensed with carbocyclic rings
A01N 43/90
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds: having two or more relevant hetero rings,…