Piperidine derivatives with pesticidal properties

Patent metadata

Field	Value
Publication number	US-9045422-B2
Application number	US-201313949803-A
Country	US
Kind code	B2
Filing date	Jul 24, 2013
Priority date	Jun 28, 2004
Publication date	Jun 2, 2015
Grant date	Jun 2, 2015

Abstract

An insecticidal acaricidal and nematicidal composition of formula I

Y is a single bond, C═O, C═S or S(O) m where m is 0, 1 or 2; the ring

 is a 6 membered aromatic ring or is a 5 or 6 membered heteroaromatic ring;
Z and

 provided that both are not N; R 1 , R 2 , R 3 , R 3a , R 4 , R 8 and Ra are specified organic groups and n and p are independently 0, 1, 2, 3 or 4; or salts or N-oxides thereof or compositions containing them in controlling insects, acarines, nematodes or molluscs. Novel compounds are also provided.

First claim

The invention claimed is:

1. A compound of formula I′

where Y is a single bond, C═O, C═S or S(O) m , where m is 0, 1 or 2;
the ring

 is a 6 membered aromatic ring or is a 5 or 6 membered heteroaromatic ring;
Z and Z′ are joined by a single or a double bond and are ═C— or —N— provided that both are not N;
R 1 is hydrogen, optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted heterocyclyloxy, cyano, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, formyl, optionally substituted heterocyclyl, optionally substituted alkylthio, NO or NR 13 R 14 where R 13 and R 14 are independently hydrogen, COR 15 , optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl or R 13 and R 14 together with the N atom to which they are attached form a group —N═C(R 16 )—NR 17 R 18 or R 13 and R 14 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C 1-6 alkyl groups; R 15 is H, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted aryloxy optionally substituted heteroaryl, optionally substituted heteroaryloxy or NR 19 R 20 ; R 16 , R 17 and R 18 are each independently H or lower alkyl; R 19 and R 20 are independently optionally substituted alkyl, optionally substituted aryl or optionally substituted heteroaryl;
R 2 is H, hydroxy, optionally substituted alkoxy or optionally substituted alkyl; or R 1 and R 2 together with the groups Y and N form a 5- or 6-membered heterocyclic ring which may optionally contain one further heteroatom selected from O, N or S and which may be optionally substituted by C 1-4 alkyl, C 1-4 haloalkyl or halogen;
R 3 is H, OH, halogen or optionally substituted alkyl;
R 3a is H or R 3 and R 3a together form a bond;
each R 4 is independently halogen, nitro, cyano, optionally substituted C 1-8 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted C 3-7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio or R 21 R 22 N where R 21 and R 22 are, independently, hydrogen, C 1-8 alkyl, C 3-7 cycloalkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 3-7 cycloalkyl(C 1-4 )alkyl, C 2-6 haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 alkoxycarbonyl or R 21 and R 22 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C 1-6 alkyl groups, or 2 adjacent groups R 4 together with the carbon atoms to which they are attached form a 4, 5, 6, or 7 membered carbocyclic or heterocyclic ring which may be optionally substituted by halogen;
n is 0, 1, 2, 3 or 4;
each Ra is independently halogen, hydroxy, cyano, optionally substituted C 1-8 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted C 3-7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio, optionally substituted arylthio or R 23 R 24 N where R 23 and R 24 are, independently, hydrogen, C 1-8 alkyl, C 3-7 cycloalkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 3-7 cycloalkyl(C 1-4 )alkyl, C 2-6 haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 alkoxycarbonyl or R 23 and R 24 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C 1-6 alkyl groups, or two Ra groups attached to the same carbon atom are ═O, ═S, ═NRb, ═CRcRd where Rb, Rc and Rd are independently H or optionally substituted alkyl; p is 0, 1, 2, 3 or 4 or one or more salts or N-oxides thereof;
and R 8 is —C(R 51 )(R 52 )—[CR 53 ═CR 54 ]z-R 55 where z is 1 or 2, R 51 and R 52 are each independently H or C 1-2 alkyl, R 53 and R 54 are each independently H, halogen, C 1-4 alkyl or C 1-4 haloalkyl and R 55 is phenyl substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino or heteroaryl substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino or salts or N-oxides thereof.

2. A compound of formula IIa

wherein; the ring

and R 3 , R 3a , R 4 , R 8 , Ra, n and p are as defined in relation to formula I′ in claim 1 and R 60 is NH 2 , NO 2 or halogen; or
a compound of formula (IIb)

wherein; the ring

each Ra is independently halogen, hydroxy, cyano, optionally substituted C 1-8 alkyl, optionally substituted C 2-6 alkenyl, optionally substituted C 2-6 alkynyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted C 3-7 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted alkylthio, optionally substituted arylthio or R 23 R 24 N where R 23 and R 24 are, independently, hydrogen, C 1-8 alkyl, C 3-7 cycloalkyl, C 3-6 alkenyl, C 3-6 alkynyl, C 3-7 cycloalkyl(C 1-4 )alkyl, C 2-6 haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 alkoxycarbonyl or R 23 and R 24 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which may be optionally substituted by one or two C 1-6 alkyl groups, or two Ra groups attached to the same carbon atom are ═O, ═S, ═NRb, ═CRcRd where Rb, Rc and Rd are independently H or optionally substituted alkyl; p is 0, 1,

Assignees

• Maienfisch Peter
• Molleyres Louis-Pierre
• Cassayre Jerome
• Cederbaum Fredik
• Corsi Camilla
• Pitterna Thomas
• Syngenta Participations Ag

Inventors

• Maienfisch Peter
• Molleyres Louis-Pierre
• Cassayre Jerome
• Cederbaum Fredik
• Corsi Camilla
• Pitterna Thomas

Classifications

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D211/52

  having an aryl radical as the second substituent in position 4 · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D211/34 Primary

  with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• A01N43/40 Primary

  six-membered rings · CPC title