Heterocyclic compounds as pesticides
View Patent ↗The present application relates to novel heterocyclic compounds, to the use thereof for controlling animal pests, which include arthropods and especially insects, and to processes for preparing the novel compounds.
1. A compound of formula (I), a salt of N-oxide thereof,
in which
A 1 and A 2 are each independently hydrogen, halogen, cyano, nitro, alkyl, cycloalkyl or alkoxy,
G 1 is C-A 1 , and
G 2 is a radical
in which the arrow marks the bond to the adjacent ring,
R 1 is hydrogen, halogen, cyano, alkyl, alkoxy, amino, alkylamino, dialkylamino, alkylthio or haloalkyl,
B is hydrogen, halogen, cyano, nitro, alkyl, cycloalkyl, haloalkyl, amino, alkylamino, dialkylamino, alkylthio or alkoxy,
G 3 is optionally substituted heterocyclyl, optionally substituted heteroaryl or optionally substituted aryl, and
G 4 is a radical selected from the group consisting of
in which the arrow in each case marks the bond to G 3 ,
X is oxygen or sulphur,
n is 1 or 2,
R 2 is in each case hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkynyl or alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl or alkylsulphonyl, in each case optionally halogen-substituted alkoxycarbonyl, in each case optionally halogen-, alkyl-, alkoxy-, haloalkyl- or cyano-substituted cycloalkylcarbonyl, or a cation,
R 3 and R 7 are each independently in each case optionally substituted alkyl, alkenyl or alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl or cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl or heteroarylalkyl, or an optionally substituted amino group, or
R 2 and R 3 in the radical (J) together with the N—S(O) n group to which they are bonded form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group,
R 5 is in each case optionally substituted alkyl, alkoxy, alkenyl or alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl or cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl or heteroarylalkyl, or an optionally substituted amino group,
R 8 is in each case a hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl or alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl or cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, in each case optionally substituted aryl, heteroaryl, arylalkyl or heteroarylalkyl, or an optionally substituted amino group, or
R 2 and R 5 in the radical (L), together with the N—C(X) group to which they are bonded form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group,
R 6 is hydrogen or alkyl, or
R 2 and R 6 in the radical (F) together with the nitrogen atoms to which they are bonded form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain at least one further heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group, or
R 2 and R 7 in the radical (E), together with the N—S(O) n group to which they are bonded form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group, or
R 6 and R 7 in the radical (F) together with the N—S(O) n group to which they are bonded form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group,
R 2 and R 8 in the radical (K) together with the nitrogen atom to which they are bonded form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group,
L is oxygen or sulphur,
R 9 and R 10 are each independently in each case optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroarylalkoxy or heteroarylalkylthio, or
R 9 and R 10 in the radical (G) together with the phosphorus atom to which they are bonded form a saturated or unsaturated and optionally substituted 5- to 7-membered ring which may contain one or two heteroatoms selected from the group consisting of oxygen (where oxygen atoms must not be immediately adjacent) and sulphur,
R 11 and R 12 are each independently in each case optionally substituted alkyl, alkenyl, alkynyl, phenyl or phenylalkyl,
Y 1 and Y 2 are each independently C═O or S(O) 2 ,
m is 1, 2, 3 or 4,
and
G 3 and G 4 together form an optionally substituted heterocycle which optionally contains one or more further heteroatoms selected from the group consisting of oxygen, nitrogen and sulphur.
2. A compound of formula (ID), a salt or N-oxide thereof,
in which
G 1 is C—H, C—F, or C—Cl,
R 1 is hydrogen or methyl,
B is hydrogen, and
G 4 is one of the (E) and (L) radicals as defined in claim 1 .
3. A composition comprising at least one compound of formula (I), a salt or N-oxide thereof according to claims 1 or 2 , and a carrier.
4. A method for controlling pests, comprising allowing at least one compound of formula (I), a salt or N-oxide thereof according to claims 1 or 2 , to act on the pests and/or their habitat.
5. A compound of formula (XVII), a salt or N-oxide thereof,
in which
G 1 is C-halogen, C-cyano, C-nitro, C-alkyl, C-cycloalkyl or C-alkoxy,
and
R 2 is as defined in claim 1 .
6. The compound according to claim 1 , a salt or N-oxide thereof,
in which
A 1 and A 2 are each independently hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or C 1 -C 6 -alkoxy,
R 1 is hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkyl,
B is hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 3 -C 6 -cycloalkyl,
G 3 is in each case optionally halogen-, cyano-, nitro-, amino-, C 1 -C 6 -alkylamino-, di(C 1 -C 6 )-alkylamino-, C 1 -C 6 -alkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -haloalkyl-, hydroxyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl-, C 2 -C 6 -alkenyl- or C 2 -C 6 -alkynyl-substituted 5-membered heteroaryl or 6-membered heteroaryl; or
G 3 is in each case optionally halogen-, cyano-, nitro-, amino-, C 1 -C 6 -alkylamino-, di-(C 1 -C 6 )-alkylamino-, C 1 -C 6 -alkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -haloalkyl-, hydroxyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl-, C 2 -C 6 -alkenyl- or C 2 -C 6 -alkynyl-substituted pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl; or
G 3 is in each case optionally halogen-, cyano-, nitro-, amino-, C 1 -C 6 -alkylamino-, di(C 1 -C 6 )-alkylamino-, C 1 -C 6 -alkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -haloalkyl-, hydroxyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl-, C 2 -C 6 -alkenyl- or C 2 -C 6 -alkynyl-substituted phenyl; or
when G 4 is one of the radicals (E), (F), (G), (H), (K), (L) and (M),
G 3 is in each case optionally halogen-, cyano-, nitro-, amino-, C 1 -C 6 -alkylamino-, di(C 1 -C 6 )-alkylamino-, C 1 -C 6 -alkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -haloalkyl-, hydroxyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl-, C 2 -C 6 -alkenyl- or C 2 -C 6 -alkynyl-substituted 5-membered heterocyclyl or 6-membered heterocyclyl, or
G 3 is in each case a radical selected from the group consisting of
(in which the arrow in each case marks the bond to G 2 and G 4 is shown for illustration only),
R 2 is in each case hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, in each case optionally halogen-substituted C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkylsulphonyl, optionally halogen-substituted C 1 -C 6 -alkoxycarbonyl, in each case optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkyl- or cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or a mono- or divalent metal ion, or an optionally C 1 -C 6 -alkyl- or aryl-C 1 -C 6 -alkyl-substituted ammonium ion,
R 3 and R 7 are each independently in each case optionally halogen-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -haloalkylthio-, C 1 -C 6 -alkylsulphinyl-, C 1 -C 6 -haloalkylsulphinyl-, C 1 -C 6 -alkylsulphonyl- or C 1 -C 6 -haloalkylsulphonyl-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, in each case optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy- or C 1 -C 6 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen; or
R 3 and R 7 are each independently in each case is a radical
(where the arrow in each case marks the bond to the sulphur atom in the radicals (E), (F) and (J)); or
R 3 and R 7 are each independently in each case optionally halogen-, cyano- (including in the alkyl moiety), nitro-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -haloalkylthio-, C 1 -C 6 -alkylsulphinyl-, C 1 -C 6 -haloalkylsulphinyl-, C 1 -C 6 -alkylsulphonyl-, C 1 -C 6 -haloalkylsulphonyl-, amino-, C 1 -C 6 -alkylamino-, di(C 1 -C 6 -alkyl)amino-, C 1 -C 6 -alkylcarbonylamino-, C 1 -C 6 -alkoxycarbonylamino-, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkynyl-, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl- or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 6 -alkyl or heteroaryl-C 1 -C 6 -alkyl, or NR′R″ in which R′ and R″ are each independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkoxylcarbonyl,
R 2 and R 3 together with the N—S(O) n group to which they are bonded, form a saturated or unsaturated and optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group; or
R 2 and R 3 together with the N—S(O) n group to which they are bonded, is a radical
(in which the arrow in each case marks the bond to G 3 S),
R 5 is in each case optionally halogen-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -haloalkylthio-, C 1 -C 6 -alkylsulphinyl-, C 1 -C 6 -haloalkylsulphinyl-, C 1 -C 6 -alkylsulphonyl- or C 1 -C 6 -haloalkylsulphonyl-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, in each case optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy- or C 1 -C 6 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, in each case optionally halogen-, cyano- (including in the alkyl moiety), nitro-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -haloalkylthio-, C 1 -C 6 -alkylsulphinyl-, C 1 -C 6 -haloalkylsulphinyl-, C 1 -C 6 -alkylsulphonyl-, C 1 -C 6 -haloalkylsulphonyl-, amino-, C 1 -C 6 -alkylamino-, di(C 1 -C 6 -alkyl)amino-, C 1 -C 6 -alkylcarbonylamino-, C 1 -C 6 -alkoxycarbonylamino-, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkynyl-, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl-, alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl- or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 6 -alkyl and heteroaryl-C 1 -C 6 -alkyl, or NR′R″ in which R′ and R″ are each independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkoxylcarbonyl,
R 8 is in each case hydrogen, or in each case optionally halogen-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -haloalkylthio-, C 1 -C 6 -alkylsulphinyl-, C 1 -C 6 -haloalkylsulphinyl-, C 1 -C 6 -alkylsulphonyl- or C 1 -C 6 -haloalkylsulphonyl-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -alkynyl, in each case optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy- or C 1 -C 6 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl and C 3 -C 6 -cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, in each case optionally halogen-, cyano- (including in the alkyl moiety), nitro-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -haloalkylthio-, C 1 -C 6 -haloalkylsulphinyl-, C 1 -C 6 -alkylsulphonyl-, C 1 -C 6 -haloalkylsulphonyl-, amino-, C 1 -C 6 -alkylamino-, di(C 1 -C 6 -alkyl)amino-, C 1 -C 6 -alkylcarbonylamino-, C 1 -C 6 -alkoxycarbonylamino-, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkynyl-, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl- or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 6 -alkyl and heteroaryl-C 1 -C 6 -alkyl, or NR′R″ in which R′ and R″ are each independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkoxylcarbonyl,
R 2 and R 5 together with the N—C(X) group to which they are bonded, form a saturated or unsaturated and optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, or C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group; or
R 2 and R 5 together with the N—C(X) group to which they are bonded, is a radical
(in which the arrow in each case marks the bond to the sulphur atom in the radical (L)),
R 6 is hydrogen or C 1 -C 6 -alkyl, or
R 2 and R 6 together with the nitrogen atoms to which they are bonded, is a saturated or unsaturated and optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -halo alkyl-, C 1 -C 6 -alkoxy-, or C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring which may contain at least one further heteroatom selected from the group of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group; or
R 2 and R 6 together with the N—N group to which they are bonded, is a radical
(where the whole radical (F) is depicted and the arrow in each case marks the bond to G 3 ),
R 2 and R 7 together with the N—S(O) n group to which they are bonded, form a saturated or unsaturated and optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, or C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring which may contain one or more further heteroatoms selected from the group of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group; or
R 2 and R 7 together with the N—S(O) n group to which they are bonded, is a radical
(in which the arrow in each case marks the bond to the C(X) group),
R 6 and R 7 together with the N—S(O) n group to which they are bonded, form a saturated or unsaturated and optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, or C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group; or
R 6 and R 7 together with the N—S(O) n group to which they are bonded, is a radical
(in which the N—R 2 group is also shown and the arrow in each case marks the bond to the C(X) group),
R 2 and R 8 together with the nitrogen atom to which they are bonded, form a saturated or unsaturated and optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, or C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring which may contain one or more further heteroatoms selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, and/or at least one carbonyl group; or
R 2 and R 8 together with the nitrogen atom to which they are bonded, is a radical
(in which the arrow in each case marks the bond to the sulphur atom in the radical (K)),
R 9 and R 10 are each independently in each case optionally halogen-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkenyloxy, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 2 -C 6 -alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, heteroaryl-C 1 -C 6 -alkoxy or heteroaryl-C 1 -C 6 -alkylthio; or
R 9 and R 10 together with the phosphorus atom to which they are bonded, form a saturated or unsaturated and optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, or C 1 -C 6 -haloalkoxy-substituted 5- to 7-membered ring which may contain one or two heteroatoms selected from the group consisting of oxygen (where oxygen atoms must not be immediately adjacent) and sulphur; or
R 9 and R 10 together with the phosphorus atom to which they are bonded, is the radical
(in which the arrow marks the bond to the nitrogen atom in the radical (G)),
R 11 and R 12 are each independently in each case optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, or C 1 -C 6 -haloalkoxy-substituted radical selected from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and phenyl-C 1 -C 6 -alkyl,
and
G 3 and G 4 together form an optionally substituted heterocycle which optionally contains further heteroatoms selected from the group consisting of oxygen, nitrogen and sulphur; or
G 3 and G 4 together form a bicycle group
(in which the arrow marks the bond to G 2 ).
7. The compound according to claim 1 , a salt or N-oxide thereof,
in which
A 1 is hydrogen, halogen or cyano,
A 2 is hydrogen,
R 1 is hydrogen or C 1 -C 4 -alkyl,
B is hydrogen,
G 3 is in each case optionally halogen-, cyano-, nitro-, amino-, C 1 -C 6 -alkylamino-, di-C 1 -C 6 -alkylamino-, C 1 -C 6 -alkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -haloalkyl-, hydroxyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl-, C 2 -C 6 -alkenyl- or C 2 -C 6 -alkynyl-substituted 5-membered heteroaryl or 6-membered heteroaryl; or
G 3 is in each case optionally halogen-, cyano-, nitro-, amino-, C 1 -C 6 -alkylamino-, di-C 1 -C 6 -alkylamino-, C 1 -C 6 -alkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -haloalkyl-, hydroxyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl-, C 2 -C 6 -alkenyl- or C 2 -C 6 -alkynyl-substituted pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl or triazinyl; or
G 3 is in each case optionally halogen-, cyano-, methyl-, methoxy-, trifluoromethyl-, amino- or dimethylamino-substituted radical selected from the group consisting of
(in which the arrow in each case marks the bond to G 2 and G 4 is also shown for illustration only); or
G 3 is in each case optionally halogen-, cyano-, nitro-, amino-, C 1 -C 6 -alkylamino-, di-(C 1 -C 6 )-alkylamino-, C 1 -C 6 -alkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -haloalkyl-, hydroxyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl-, C 2 -C 6 -alkenyl- or C 2 -C 6 -alkynyl-substituted phenyl; or
when G 4 is radicals (E) or (L),
G 3 is in each case optionally halogen-, cyano-, nitro-, amino-, C 1 -C 6 -alkylamino-, di(C 1 -C 6 )-alkylamino-, C 1 -C 6 -alkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio-, C 1 -C 6 -alkylcarbonyl-, C 1 -C 6 -alkoxycarbonyl-, C 2 -C 6 -alkenyl- or C 2 -C 6 -alkynyl-substituted 5-membered heterocyclyl; or
G 3 is in each case a 6-membered heterocyclyl selected from the group consisting of
(in which the arrow in each case marks the bond to G 2 and G 4 is also shown for illustration only),
G 4 is a radical (E) or (F)
X is oxygen,
n is 2,
R 2 is in each case hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, cyano-C 1 -C 4 alkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkylsulphonyl, in each case optionally halogen-substituted C 1 -C 4 -alkoxycarbonyl, optionally halogen-, C 1 -C 4 -haloalkyl- or cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or a mono- or divalent metal ion, or an optionally C 1 -C 4 -alkyl- or aryl-C 1 -C 4 -alkyl-substituted ammonium ion; or
R 2 is hydrogen, methyl, ethyl, CH 2 OCH 3 , CH 2 OCH 2 CH 3 , COCH 3 , COCH 2 CH 3 , cyclopropyl, Na + , K + or + N(CH 3 ) 4 ,
R 5 is in each case optionally halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl- or C 1 -C 4 -haloalkylsulphonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl or C 2 -C 4 -alkynyl, in each case optionally halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, or C 1 -C 4 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl or C 3 -C 4 -cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen; or
R 5 is in each case a radical
(where the arrow in each case marks the bond to the carbon atom in the radical (L)); or
R 5 is in each case optionally halogen-, cyano- (including in the alkyl moiety), nitro-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl-, C 1 -C 4 -haloalkylsulphonyl-, amino-, C 1 -C 4 -alkylamino-, di(C 1 -C 4 -alkyl)amino-, C 1 -C 4 -alkylcarbonylamino-, C 1 -C 4 -alkoxycarbonylamino-, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl-, C 2 -C 4 -alkenyl-, C 2 -C 4 -alkynyl-, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl-, C 1 -C 4 -alkylcarbonyl-, C 1 -C 4 -alkoxycarbonyl- or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl or heteroaryl-C 1 -C 4 -alkyl, or NR′R″ in which R′ and R″ are each independently hydrogen or C 1 -C 4 -alkyl, and
R 7 is in each case optionally halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl- or C 1 -C 4 -haloalkylsulphonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl or C 2 -C 4 -alkynyl, in each case optionally halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, or C 1 -C 4 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl or C 3 -C 4 -cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen; or
R 7 is in each case a radical
(where the arrow in each case marks the bond to the sulphur atom in the radical (E)); or
R 7 is in each case optionally halogen-, cyano- (including in the alkyl moiety), nitro-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl-, C 1 -C 4 -haloalkylsulphonyl-, amino-, C 1 -C 4 -alkylamino-, di(C 1 -C 4 -alkylamino-, C 1 -C 4 -alkylcarbonylamino-, C 1 -C 4 -alkoxycarbonylamino-, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl-, C 2 -C 4 -alkenyl-, C 2 -C 4 -alkynyl-, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl-, C 1 -C 4 -alkylcarbonyl-, C 1 -C 4 -alkoxycarbonyl- or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl or heteroaryl-C 1 -C 4 -alkyl, or NR′R″, in which R′ and R″ are each independently hydrogen, C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl; or
R 7 is in each case methyl, ethyl, i-propyl, CF 3 , CHF 2 , CH 2 F, CH 2 CF 3 , cyclopropyl, cyclopropylmethyl, cyclopropylethyl, dimethylamino, diethylamino, phenyl or benzyl.
8. The compound according to claim 1 , a salt or N-oxide thereof,
in which
A 1 is hydrogen, fluorine or chlorine,
A 2 is hydrogen,
the structural element containing G 1 is
in which the broken line marks the bond to G 2 ,
R 1 is hydrogen or methyl,
B is hydrogen,
G 3 is an optionally halogen-, cyano-, methyl-, methoxy-, trifluoromethyl-, amino- or dimethylamino-substituted radical selected from the group consisting of
(in which the arrow in each case marks the bond to G 2 and G 4 is shown for illustration purpose only),
G 4 is a radical (E) or (L)
X is oxygen,
n is 2,
R 2 is in each case hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl, cyano-C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, optionally halogen-substituted C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -alkylsulfonyl, in each case optionally halogen-substituted C 1 -C 4 -alkoxycarbonyl, optionally halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -halogenalkyl- or cyano-substituted C 3 -C 6 -cycloalkylcarbonyl, or in each case a mono- or divalent metal ion, or an optionally C 1 -C 4 -alkyl- or aryl-C 1 -C 4 -alkyl-substituted ammonium ion,
R 5 is in each case optionally halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl- or C 1 -C 4 -haloalkylsulphonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl, in each case optionally halogen-, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 4 -cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen, or
R 5 is in each case a group
(where the arrow in each case marks the bond to the carbon atom in the (L) radical), or
R 5 is in each case optionally halogen-, cyano- (including in the alkyl moiety), nitro-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl-, C 1 -C 4 -haloalkylsulphonyl-, amino-, C 1 -C 4 -alkylamino-, di(C 1 -C 4 -alkyl)amino-, C 1 -C 4 -alkylcarbonylamino-, C 1 -C 4 -alkoxycarbonylamino-, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl-, C 2 -C 4 -alkenyl-, C 2 -C 4 -alkynyl-, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl-, C 1 -C 4 -alkylcarbonyl-, C 1 -C 4 -alkoxycarbonyl- or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl, or NR′R″ in which R′ and R″ are each independently hydrogen or C 1 -C 4 -alkyl, and
R 7 is in each case optionally halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl- or C 1 -C 4 -haloalkylsulphonyl-substituted C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl or C 2 -C 4 -alkynyl, in each case optionally halogen-, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl or C 3 -C 4 -cycloalkenyl, in which the rings may contain at least one heteroatom selected from the group consisting of sulphur, oxygen (where oxygen atoms must not be immediately adjacent) and nitrogen; or
R 7 is in each case a radical
(where the arrow in each case marks the bond to the sulphur atom in the (E) radical); or
R 7 is in each case optionally halogen-, cyano- (including in the alkyl moiety), nitro-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 3 -C 6 -cycloalkyl-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -haloalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl-, C 1 -C 4 -haloalkylsulphonyl-, amino-, C 1 -C 4 -alkylamino-, di(C 1 -C 4 -alkyl)amino-, C 1 -C 4 -alkylcarbonylamino-, C 1 -C 4 -alkoxycarbonylamino-, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl-, C 2 -C 4 -alkenyl-, C 2 -C 4 -alkynyl-, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl-, C 1 -C 4 -alkylcarbonyl-, C 1 -C 4 -alkoxycarbonyl- or aminocarbonyl-substituted aryl, heteroaryl, aryl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl, or NR′R″, in which R′ and R″ are each independently hydrogen or C 1 -C 4 -alkyl.
9. The compound according to claim 8 , a salt or N-oxide thereof,
in which
R 2 is hydrogen, methyl, ethyl, CH 2 OCH 3 , CH 2 OCH 2 CH 3 , COCH 3 , COCH 2 CH 3 , CH 2 CN, propynyl, cyclopropyl, Na + , K + or + N(CH 3 ) 4 ,
R 5 is methyl, ethyl, i-propyl, CF 3 , CHF 2 , CH 2 F, CH 2 CF 3 , cyclopropyl, dimethylamino, diethylamino, phenyl or benzyl, and
R 7 is methyl, ethyl, i-propyl, CF 3 , CHF 2 , CH 2 F, CH 2 CF 3 , cyclopropyl, dimethylamino, diethylamino, phenyl or benzyl.
10. The compound according to claim 9 , a salt or N-oxide thereof, in which
the structural element containing G 1 is
R 1 is hydrogen,
G 3 is
(in which the arrow marks the bond to G 2 , and G 4 is also shown for illustration only), and
G 4 is the radical (E),
(in which the arrow marks the bond to the adjacent ring).