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US 6,150,374 AGranted
Substituted cycloalkenes, process of preparing them and method of using them as pesticides
AssigneeBayer Aktiengesellschaft
InventorsHerbert Gayer, Peter Gerdes, Ralf Tiemann, Stefan Dutzmann, Klaus Stenzel
Life of this patent
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Abstract
The invention relates to novel substituted cycloalkenes of the formula (I), ##STR1## to a plurality of processes for their preparation, and to novel intermediates and a plurality of processes for their preparation.
Claims12
A compound of the formula (I) ##STR70## in which E represents nitrogen,
- G represents a single bond, represents oxygen, sulphur, or represents respectively optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkanediyl or alkynediyl or cycloalkyl-substituted alkenediyl or one of the groupings below
- --Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--, --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 --, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, --N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, --S(O).sub.n --CH.sub.2 --, --C(R.sup.1).dbd.N--O--, --C(R.sup.1).dbd.N--O--CH.sub.2 --, --N(R.sup.2)--, --CQ--N(R.sup.2)--, --N(R.sup.2)--CQ--, --Q--CQ--N(R.sup.2)--, --N.dbd.C(R.sup.1)--Q--CH.sub.2 --, --N(R.sup.2)--CQ--Q--, --CQ--N(R.sup.2)--CQ--Q--, --N(R.sup.2)--CQ--Q--CH.sub.2 --, --Q--C(R.sup.1).dbd.N--O--CH.sub.2 --, --N(R.sup.2)--C(R.sup.1).dbd.N--O--CH.sub.2 --, --O--CH.sub.2 --C(R.sup.1).dbd.N--O--CH.sub.2 --, --N.dbd.N--C(R.sup.1).dbd.N--O--CH.sub.2 --, --CH.sub.2 --O--N.dbd.C(R.sup.1)--, --T--Ar.sup.1 or --T--Ar.sup.1 --Q--, where
- Ar.sup.1 represents optionally substituted arylene, heteroarylene, or cycloalkylene or Ar.sup.1 represents an aliphatic ring which is doubly attached and in which one or more carbon atoms are replaced by hetero atoms, independently selected from the group consisting of oxygen, sulphur and nitrogen,
- n represents the number 0, 1 or 2,
- Q represents oxygen or sulphur,
- R.sup.1 represents hydrogen, cyano or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
- R.sup.2 represents hydrogen, hydroxyl, cyano or respectively optionally substituted alkyl, alkoxy or cycloalkyl and
- T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, CH.sub.2 --S-- or represents optionally substituted alkanediyl,
- m represents 0, 1 or 2,
- R represents alkyl, alkoxy, amino, hydroxylamino, alkoxyamino, alkylamino or dialkylamino,
- Y represents methylene, and
- Z represents respectively optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl.
9 more elements
Process of preparing a compound of the formula (I) ##STR71## in which E represents nitrogen,
- G represents a single bond, represents oxygen, sulphur, or represents respectively optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkanediyl or alkynediyl or cyclaolkyl-substituted alkenediyl or one of the groupings below
- --Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--, --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 --, --CH.sub.2 --Q--CQ--, --O--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, --N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, --S(O).sub.n --CH.sub.2 --, --C(R.sup.1).dbd.N--O--, --C(R.sup.1).dbd.N--O--CH.sub.2 --, --N(R.sup.2)--, --CQ--N(R.sup.2)--, --N(R.sup.2)--CQ--, --Q--CQ--N(R.sup.2)--, --N.dbd.C(R.sup.1)--Q--CH.sub.2 --, --N(R.sup.2)--CQ--Q--, --CQ--N(R.sup.2)--CQ--Q--, --N(R.sup.2)--CQ--Q--CH.sub.2 --, --Q--C(R.sup.1).dbd.N--O--CH.sub.2 --, --N(R.sup.2)--C(R.sup.1).dbd.N--O--CH.sub.2 --, --O--CH.sub.2 --C(R.sup.1).dbd.N--O--CH.sub.2 --, --N.dbd.N--C(R.sup.1).dbd.N--O--CH.sub.2 --, --CH.sub.2 --O--N.dbd.C(R.sup.1)--, --T--Ar.sup.1 or --T--Ar.sup.1 --Q--, where
- Ar.sup.1 represents optionally substituted arylene, heteroarylene, or cycloalkylene or Ar.sup.1 represents an aliphatic ring which is doubly attached and in which one or more carbon atoms are replaced by hetero atoms, independently selected from the group consisting of oxygen, sulphur and nitrogen,
- n represents the number 0, 1 or 2,
- Q represents oxygen or sulphur,
- R.sup.1 represents hydrogen, cyano or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
- R.sup.2 represents hydrogen, hydroxyl, cyano or respectively optionally substituted alkyl, alkoxy or cycloalkyl and
- T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, CH.sub.2 --S-- or represents optionally substituted alkanediyl,
- m represents 0, 1 or 2,
- R represents alkylamino or dialkylamino,
- Y represents methylene, and
- Z represents respectively optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl.
- comprising reacting an amide of the formula (XIV):
- ##STR72## in which E, G, m, Y and Z are each as defined above, with an alkylating agent of the general formula (XIII)
- R.sup.9 --X.sup.4 (XIII)
- in which
- R.sup.9 represents alkyl,
- X.sup.4 represents halogen or --O--SO.sub.2 --R.sup.10 and
- R.sup.10 represents --O--R.sup.9, aklyl or optionally substituted aryl,
- optionally in the presence of a diluent and optionally in the presence of an acid acceptor.
17 more elements
Dependencies are inferred from the claim text.