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US 2014/0371240 A1Published application
Novel insecticidal aromatic amides
AssigneeBayer Intellectual Property GmbH
InventorsMichael Maue, Tobias Kapferer, Friedrich August Muehlthau, Olga Malsam
Life of this patent
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Abstract
The invention relates to compounds of the general formulae (I) and (II) in which the radicals A1, A2, A3, A4, M1, M2, M3, Q, R1, T, W1 and W2 have the meaning given in the description and to the use of the compounds for controlling animal pests. The invention furthermore relates to processes and intermediates for preparing the compounds of formula (I).
Claims14
Compound of formula (Ia)
- in which
- R1 represents hydrogen or the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, cyano-C1-C2-alkyl, aryl-(C1-C3)-alkyl, heteroaryl-(C1-C3)-alkyl;
- A1 represents CR2,
- A2 represents CR3,
- A3 represents CR4 or nitrogen and
- A4 represents CR5, where
- R2, R3 and R5 independently of one another represent hydrogen, halogen, CN, NO2, optionally substituted C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphinyl, C1-C6-haloalkylsulphinyl, C1-C6-alkyl sulphonyl, C1-C6-haloalkylsulphonyl, C1-C6-alkylamino, N,N-di-C2-C6-alkylamino, N—C2-C7-alkylaminocarbonyl, N—C2-C7-cycloalkylaminocarbonyl or C2-C4-alkoxycarbonyl;
- R4 represents hydrogen, halogen, CN, NO2, optionally substituted C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphinyl, C1-C6-haloalkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-haloalkylsulphonyl, C1-C6-alkylamino, N,N-di-C2-C6-alkylamino, N—C2-C7-alkylaminocarbonyl, N—C2-C7-cycloalkylaminocarbonyl or C2-C4-alkoxycarbonyl or N-heteroaryl;
- if the grouping A3 does not represent nitrogen, R3 and R4 together with the carbon to which they are attached may form a 5- or 6-membered ring which contains 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or
- R2 and R3 together with the carbon to which they are attached may form a 6-membered ring which contains 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom;
- M1 and M2 each independently of one another represent hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C2-C7-alkoxycarbonyl, C1-C6-haloalkyl, cyano or cyano-C1-C2-alkyl, or
- M1 and M2 with the carbon atom to which they are attached form an optionally substituted 3-, 4-, 5- or 6-membered ring which optionally contains 0, 1 or 2 nitrogen atoms and/or 0, 1 or 2 oxygen atoms and/or 0, 1 or 2 sulphur atoms,
- M3 represents hydrogen, optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, cyano-C1-C2-alkyl, aryl-(C1-C3)-alkyl or heteroaryl-(C1-C3)-alkyl,
- W1 and W2 independently of one another represent oxygen or sulphur;
- p assumes the value 1,
- Q represents hydrogen or the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, cyano-C1-C2-alkyl, C1-C5-heterocycloalkyl, C1-C4-alkoxy, C4-C7-alkylcycloalkyl, C4-C7-cycloalkylalkyl, C2-C7-alkylcarbonyl, C1-C6-alkylaldehyde, C1-C6-hydroxyalkyl, C2-C7-alkoxycarbonyl, C1-C6-haloalkyl, represents formyl, hydroxy, halogen, cyano, aryl, heteroaryl or represents a grouping OR7, SR7, NR6R8, where
- R6 represents hydrogen or the optionally substituted groupings C1-C6-alkyl, aryl, heteroaryl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl and C4-C7-cycloalkylalkyl, C2-C7-alkylcarbonyl, C2-C7-alkoxycarbonyl;
- R7 is selected from the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl and C4-C7-cycloalkylalkyl;
- R8 is selected from hydrogen or the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl and C4-C7-cycloalkylalkyl;
- where
- Z1 and Z2 independently of one another represent hydrogen, halogen, cyano, nitro or the optionally substituted groupings C1-C6-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphinyl, C1-C6-haloalkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-haloalkylsulphonyl, N,N-di-(C1-C6)-alkylamino, —S (O)2NR —S(O)(═NR16)R17 or represent optionally substituted phenyl or pyridinyl;
- Z5 represents hydrogen, optionally substituted C1-C6-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, or optionally substituted phenyl or pyridinyl;
- R13 is selected from hydrogen or one of the optionally substituted groupings C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl, C4-C7-cycloalkylalkyl, C2-C7-alkylcarbonyl, C2-C7-alkoxycarbonyl, aryl or heteroaryl;
- R14 is selected from hydrogen or one of the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl and C4-C7-cycloalkylalkyl;
- R15 is selected from optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl, C4-C7-cycloalkylalkyl, C1-C4-haloalkyl, aryl or heteroaryl;
- R16 is selected from hydrogen or one of the optionally substituted groupings C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl, C4-C7-cycloalkylalkyl, C2-C7-alkylcarbonyl, C2-C7-alkoxycarbonyl, cyano or nitro;
- and
- R17 is selected from hydrogen, optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl and C4-C7-cycloalkylalkyl, aryl or heteroaryl.
25 more elements
Compound of formula (III)
- in which
- R1 represents hydrogen, optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, cyano-C1-C2-alkyl, aryl-(C1-C3)-alkyl or heteroaryl-(C1-C3)-alkyl,
- the chemical grouping
- A1 represents CR2 or nitrogen,
- A2 represents CR3 or nitrogen,
- A3 represents CR4 or nitrogen and
- A4 represents CR5 or nitrogen,
- but where not more than three of the chemical groupings A1 to A4 simultaneously represent nitrogen;
- R2, R3, R4 and R5 independently of one another represent hydrogen, halogen, CN, NO2, optionally substituted C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphinyl, C1-C6-haloalkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-haloalkylsulphonyl, C1-C6-alkylamino, N,N-di-C2-C6-alkylamino, N—C2-C7-alkylaminocarbonyl, N—C2-C7-cycloalkylaminocarbonyl, C2-C4-alkoxycarbonyl, aryl, heteroaryl or N-heteroaryl;
- if none of the groupings A2 and A3 represents nitrogen, R3 and R4 together with the carbon atom to which they are attached may form a 5- or 6-membered ring which contains 0, 1 or 2 nitrogen atoms and/or 0 or 1 oxygen atom and/or 0 or 1 sulphur atom, or
- if none of the groupings A1 and A2 represents nitrogen, R2 and R3 together with the carbon atom to which they are attached may form a 5- or 6-membered ring which contains 0, 1 or 2 nitrogen atoms;
- T represents (T-6),
- where
- Z1 represents hydrogen, halogen, cyano, nitro, optionally substituted C1-C6-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphinyl, C1-C6-haloalkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-haloalkylsulphonyl, N,N-di-(C1-C6)-alkylamino, —C(═W)NR11R10—C(═W)OR′2, —S(O)2NR13R14, —S(O)—R15, —S(O)(═NR16)R17 or optionally substituted phenyl or pyridinyl;
- Z2 represents C1-C6-haloalkyl;
- Z5 represents hydrogen, optionally substituted C1-C6-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulphinyl, C1-C6-haloalkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-haloalkylsulphonyl, N, N-di-(C1-C6)-alkyl amino, —C(═W)NR11R10, —C(═W)OR12, —S(O)2NR13R14, —S(O)nR15, —S(O)(═NR16)R17 or optionally substituted phenyl or pyridinyl;
- R10 is selected from hydrogen or the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C2-C7-alkylcarbonyl and C2-C7-alkoxycarbonyl;
- R11 is selected from hydrogen or the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C2-C7-alkylcarbonyl and C2-C7-alkoxycarbonyl, aryl or heteroaryl;
- R12 is selected from hydrogen or the optionally substituted groupings C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C7-alkylcycloalkyl and C4-C7-cycloalkylalkyl, aryl or heteroaryl;
- R13 is selected from hydrogen or the optionally substituted groupings C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl, C4-C7-cycloalkylalkyl, C2-C7-alkylcarbonyl and C2-C7-alkoxycarbonyl, aryl or heteroaryl;
- R14 is selected from hydrogen or the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl and C4-C7-cycloalkylalkyl;
- R15 is selected from the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl and C4-C7-cycloalkylalkyl, C1-C4-haloalkyl, aryl or heteroaryl;
- R16 is selected from hydrogen or the optionally substituted groupings C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl, C4-C7-cycloalkylalkyl, C2-C7-alkylcarbonyl, C2-C7-alkoxycarbonyl, cyano or nitro;
- R17 is selected from hydrogen or the optionally substituted groupings C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C4-C7-alkylcycloalkyl, C4-C7-cycloalkyl, aryl or heteroaryl;
- n may assume the value 0, 1 or 2;
- Y represents CN or CH2NH2.
23 more elements
Dependencies are inferred from the claim text.