Compounds based on alkoxyheteroaryl-carboxamide or -thioamide

Claims

1. A compound of formula (I), Where A represents O or S; X represents N or CR 8 ; Y represents N or CR 8 ; Z represents N or CR 8 ; provided that at least one of X, Y, Z is N; R 1represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkoxy-C1-C6 alkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 halocycloalkyl-C1-C6 alkyl, cyano-C1-C6 alkyl, cyano-C3-C6 cycloalkyl, cyano-C3-C6 cycloalkyl-C1-C6 alkyl, cyanoheterocycloalkyl, hydroxy-C3-C6 cycloalkyl, C1-C6-alkylcarbonyloxy-C3-C6-cycloalkyl, C1-C6-alkylsulfonyloxy-C3-C6-cycloalkyl, C1-C6-alkoxy-C3-C6-cycloalkyl, C1-C6-haloalkoxy-C3-C6-cycloalkyl, C1-C6-alkylthio-C3-C6-cycloalkyl, C1-C6-haloalkylthio-C3-C6-cycloalkyl, C1-C6-alkylsulfinyl-C3-C6-cycloalkyl, C1-C6-halogenalkylsulfinyl-C3-C6-cycloalkyl, C1-C6-alkylsulfonyl-C3-C6-cycloalkyl, C1-C6-haloalkylsulfonyl-C3-C6-cycloalkyl, C2-C6-alkynyl-C3-C6-cycloalkyl, C1-C6-alkoxycarbonyl-C3-C6-cycloalkyl, carboxy-C3-C6-cycloalkyl, carbamoyl-C3-C6-cycloalkyl,C1-C6-alkylaminocarbonyl-C3-C6-cycloalkyl (which may be mono- or polysubstituted by R), C4-C8-bicycloalkyl, C1-C6-alkoxyimino, phenyl (which may be mono- or polysubstituted by R, 10 ), phenyl-C1-C6-alkyl (phenyl may be mono- or polysubstituted with R 10 ), heteroaryl (heteroaryl may be mono- or polysubstituted with R 10 ), heteroaryl-C1-C6-alkyl (heteroaryl may be mono- or polysubstituted with R 10 ), heteroaryl-C3-C6-cycloalkyl (heteroaryl may be mono- or polysubstituted with R 10 ), heterocycloalkyl (which may be substituted by R 8 ), heterocycloalkyl-C1-C6-alkyl (which may be substituted by R 8 ) or heterocycloalkyl-C3-C6-cycloalkyl (heterocycloalkyl may be substituted with R 8 ); R 2represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 haloalkoxy, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 halocycloalkyl-C1-C6 alkyl, phenyl (which may be mono- or polysubstituted by R 10 ), phenyl-C1-C6-alkyl (phenyl may be mono- or polysubstituted with R 10 ), heteroaryl (heteroaryl may be mono- or polysubstituted with R 10 ), heteroaryl-C1-C3-alkyl (heteroaryl can be monosubstituted or polysubstituted with R 10 ), cyano, cyano-C1-C6-alkyl, cyano-C3-C6-cycloalkyl, hydroxy, formyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-cycloalkylcarbonyl, benzoyl, which is mono- or polysubstituted with R 10, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyloxycarbonyl, carbamoyl, C1-C6-alkylaminocarbonyl (amino group can be substituted with R), C1-C6-alkoxycarbonyl C1-C6-alkylamino (amino group can be substituted with R 8 ), C1-C6-alkoxycarbonylamino (the amino group can be substituted with R 8 ), (C1-C6-alkylthio)carbonyl, (C1-C6-alkyl)thiocarbonyl, (C1-C6-alkoxy)thiocarbonyl, thiocarbamoyl, C1-C6-alkylaminothiocarbonyl (the amino group may be substituted with R 8 ), C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, sulfamoyl, C1-C6-alkylaminosulfonyl (the amino group may be substituted with R 8 ), C1-C6-alkoxycarbonyl-C1-C6-alkyl, aminocarbonyl-C1-C6-alkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkyl (the amino group may be substituted with R 8 ), C3-C6-cycloalkylaminocarbonyl-C1-C6-alkyl (the amino group may be substituted with R 8), C1-C6-haloalkylaminocarbonyl-C1-C6-alkyl (the amino group may be substituted with R 8 ), C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-haloalkylcarbonyl-C1-C6-alkyl, C1-C6-alkylcarbonyloxy-C1-C6-alkyl, C1-C6-alkoxycarbonyloxy-C1-C6-alkyl, C1-C6-alkoxycarbonylamino-C1-C6-alkyl (the amino group may be substituted with R 8 ), hydroxyimino, hydroxyamino-C1-C6-alkyl, C1-C6-alkoxyimino, C1-C6-alkoxyimino-C1-C6-alkyl or C1-C6-haloalkoxyimino-C1-C6-alkyl; R 3 is halogen, cyano, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, C1-C6 haloalkyl or C1-C6 haloalkoxy; R 4 represents or R 5 is C1-C3-alkylsulfonylamino, C1-C3-haloalkylsulfonylamino, or C3-C6-cycloalkylsulfonylamino, wherein any of said amino groups is unsubstituted or substituted with R 6; and where any of said cycloalkyl groups may be mono- or polysubstituted with R 9 ; R 6 is C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy-C1-C6 alkyl, cyano-C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C6 alkylcarbonyl or C1-C6 alkoxycarbonyl; R 8 represents hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl or cyano; R 9 is halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl or cyano; and R 10is halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 halocycloalkyl-C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylthio-C1-C6 alkyl, C1-C6 haloalkylthio-C1-C6 alkyl, C1-C6 alkylsulfonyloxy, C1-C6 haloalkylsulfonyloxy, phenyl (which may be mono- or polysubstituted by independent selection from halogen, C1-C6 alkyl and C1-C6 haloalkyl), phenyl-C1-C6 alkyl, phenyl-C1-C6 alkoxy, cyano and nitro; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide of the compound of formula (I).

2. The compound of claim 1, wherein the compound of formula (I) is represented by formula (I-1), (I-2), (I-3) or (I-4), where A, R 1 , R 2 , R 3 and R 4 are as defined in paragraph 1, 3. The compound of claim 1, wherein the compound of formula (I) is represented by formula (I-1a), (I-2a), (I-3a) or (I-4a), where R 1 , R 2 , R 3 and R 6 are as defined in paragraph 1; and where R 7 independently of (I-1a), (I-2a), (I-3a) and (I-4a) is selected from C1-C3-alkyl, C1-C3-haloalkyl or C3-C6-cycloalkyl, wherein said cycloalkyl group may be mono- or polysubstituted with R 9 , where R 9 is as defined in paragraph 1, 4. Compounds according to claim 3, wherein the compound of formula (I), represented by formula (I-1a), (I-2a), (I-3a) or (I-4a), is the (S)-enantiomer.

5. The connection according to any one of paragraphs 1-4, where R 1represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkynyl, C3-C6 cycloalkyl, cyano-C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, heterocyclyl, or C1-C6 alkoxy-C3-C6 cycloalkyl; and R 2 represents hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C1-C6 alkoxy-C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C6 alkyl or C1-C8 alkylcarbonyl.

6. A connection according to any one of paragraphs 1-5, where R 1 represents C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered heterocyclyl containing SO2, or cyano-C3-C4-cycloalkyl; and R 2 represents hydrogen, C1-C3 alkyl, C1-C3 alkylcarbonyl or C1-C3 alkoxycarbonyl.

7. A connection according to any one of paragraphs 1-6, where R 3 is halogen, C1-C6 alkyl or cyano.

8. The compound according to claim 7, wherein R is chlorine, bromine or methyl.

9. A connection according to any one of paragraphs 1-8, where R 5 is isopropylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, difluoromethylsulfonylamino or cyclopropylsulfonylamino.

10. A connection according to any one of paragraphs 1-8, where R 6 represents hydrogen, C1-C3 alkyl, C1-C3 alkoxy-C1-C3 alkyl, C3-C4 cycloalkyl-C1-C3 alkyl or C1-C3 alkylcarbonyl.

11. A method for preparing a compound of formula (I) (where A is O) comprising converting a compound of formula (II) where R 3 , R 4 , X, Y, Z are as defined in any of paragraphs 1-10, using a compound of formula (III), where R 1 and R 2 are as defined in any of paragraph 1, paragraph 5 or paragraph 6, via an intermediate compound which is an acid chloride or an activated acylating agent of formula (IV), 12. A composition comprising a compound according to any one of claims 1 to 10, one or more auxiliary agents, and a diluent, and optionally one or more other active ingredients.

13. A method for controlling and monitoring insects, mites or molluscs which comprises applying to a pest, to a habitat of a pest or to a plant susceptible to attack by a pest, an insecticidally, acaricidal or molluscicidally effective amount of a compound of formula I according to any one of claims 1 to 10 or a composition according to claim 12.

14. A method for protecting plant propagation material from damage by insects, mites or mollusks, which comprises treating the propagation material or the area where the propagation material is planted with an effective amount of a compound of formula I according to any one of claims 1 to 10 or a composition according to claim 12.

15. Plant propagation material, such as seed, containing or treated with a compound of formula I according to any one of claims 1 to 10, or to which it is attached.