US2019104733A1PendingUtilityA1
Malononitrile Compounds for Controlling Animal Pests
Est. expiryDec 14, 2032(~6.4 yrs left)· nominal 20-yr term from priority
Inventors:Ralph PauliniMatthias PohlmanSebastian SoergelHenricus Maria Martinus BastiaansSarah ThompsonCecille Ebuenga DoyogAnna Malveda UmaliRhoel Suiza Cosare
C07D 241/16A61P 33/14C07D 213/57C07D 239/30C07D 237/12A61P 33/00C07D 239/34C07D 239/26C07D 213/61A01N 43/40C07D 213/64C07C 255/09C07D 241/12C07C 255/10A61P 33/10A01N 43/58A01N 37/34C07D 239/28C07C 255/13A01N 43/54C07D 237/08
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Claims
Abstract
The invention relates to the use of a compound of formula (I) or a salt thereof for combating animal pests, where the symbols and indices are defined in the specification.
Claims
exact text as granted — not AI-modified1 . (canceled)
2 . A compound of formula (I)
or a salt or N-oxide thereof, wherein
Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R 5 ; or naphthyl unsubstituted or substituted with 1, 2, 3, 4, 5, 6 or 7 substituents R 5 ;
Q is a 6-membered aromatic heterocyclic ring containing 1, 2, 3 or 4 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2, 3 or 4 substituents R 6 ;
R 1 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R 7 ;
R 2 is hydrogen or halogen; or
R 1 and R 2 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group;
R 3 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R 7 ;
R 4 is hydrogen or halogen; or
R 3 and R 4 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group;
each R 5 , R 6 is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF 5 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R a ;
C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkenyl, wherein the carbon atoms of the aforementioned cycloaliphatic radicals are unsubstituted or substituted with one or more R b ;
phenyl unsubstituted or substituted with up to 5 R c ;
a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO, SO 2 , wherein the aforementioned ring is unsubstituted or substituted with up to 5 R d ;
Si(R e ) 3 , OR f , SR f , OS(O) x R h , S(O) x R h , N(R i ) 2 , N(R i )C(═O)R m , OC(═O)R m , C(═O)R m , C(═O)OR f , C(═NR i )R m , C(═S)R m ; or
two R 5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of CH 2 CH 2 CH 2 CH 2 , N═CH—CH═CH, CH═N—CH═CH, N═CH—N═CH, N═CH—CH═N, OCH 2 CH 2 CH 2 , OCH═CHCH 2 , CH 2 OCH 2 CH 2 , OCH 2 CH 2 O, OCH 2 OCH 2 , CH 2 CH 2 CH 2 , CH═CHCH 2 , CH 2 CH 2 O, CH═CHO, CH 2 OCH 2 , CH 2 C(═O)O, C(═O)OCH 2 , O(CH 2 )O, SCH 2 CH 2 CH 2 , SCH═CHCH 2 , CH 2 SCH 2 CH 2 , SCH 2 CH 2 S, SCH 2 SCH 2 , CH 2 CH 2 S, CH═CHS, CH 2 SCH 2 , CH 2 C(═S)S, C(═S)SCH 2 , S(CH 2 )S, CH 2 CH 2 NR K , CH 2 CH═N, CH═CH—NR K , OCH═N, SCH═N and form together with the carbon atoms the two R 5 are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted or substituted with 1 or 2 substituents selected from ═O, OH, CH 3 , OCH 3 , halogen, halomethyl and halomethoxy;
each R 7 is independently selected from the group consisting of halogen, cyano, hydroxy, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 1 -C 6 -alkylthio, (C 1 -C 6 -alkoxy)carbonyl, OSi(R e ) 3 , wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted, partially or fully halogenated and/or oxygenated;
each R a is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, Si(R e ) 3 , OR A , SR A , OSO 2 R B , S(O) x R B , —S(O) x N(R D ) 2 , N(R D ) 2 , C(═O)N(R D ) 2 , C(═S)N(R D ) 2 , C(═O)OR A ,
phenyl unsubstituted or substituted with up to 5 R E ;
a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO, SO 2 , wherein the aforementioned ring is unsubstituted or substituted with up to 5 R E , or
two R a present on one carbon atom are together ═O, ═C(R F ) 2 , ═NR D , ═NOR A , ═NNR D , or
two R a form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R a are bonded to;
each R b is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylthio, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, Si(R G ) 3 , OR H , SR H , OSO 2 R J , S(O) x R J , —S(O) x N(R K ) 2 , N(R K ) 2 , C(═O)N(R K ) 2 , C(═S)N(R K ) 2 , C(═O)OR H , or
two R b present on one carbon atom are together ═O, ═C(R L ) 2 , ═NR K , ═NOR H , ═NNR K , or
two R b form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R b are bonded to;
each R c is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF 5 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
Si(R G ) 3 , OR H , SR H , OS(O) x R J , S(O) x R J , —S(O) x N(R K ) 2 , N(R K ) 2 , C(═O)R N , C(═O)OR H , C(═NR K )R N , C(═O)N(R K ) 2 , C(═S)N(R K ) 2 ;
each R d is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF 5 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
Si(R G ) 3 , OR H , SR H , OS(O) x R J , S(O) x R J , —S(O) x N(R K ) 2 , N(R K ) 2 , C(═O)R N , C(═O)OR H , C(═NR K )R N , C(═O)N(R K ) 2 , C(═S)N(R K ) 2 , or
two R d present on one atom of a saturated or partially unsaturated heterocyclic ring are together ═O, ═C(R L ) 2 ; ═NR K , ═NOR H or ═NNR K ;
each R e is independently selected from the group consisting of halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, C 1 -C 6 haloalkoxyalkyl,
phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO 2 ;
each R f is independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
Si(R e ) 3 , S(O) x R B , —S(O) x N(R D ) 2 , N(R D ) 2 , —N═C(R F ) 2 , C(═O)R Q , C(═O)N(R D ) 2 , C(═S)N(R D ) 2 , C(═O)OR A ,
phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO 2 ;
each R h is independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
N(R D ) 2 , —N═C(R F ) 2 , C(═O)R Q , C(═O)N(R D ) 2 , C(═S)N(R D ) 2 , C(═O)OR A , phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO 2 ;
each R i is independently selected from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
S(O) x R B , —S(O) x N(R D ) 2 , C(═O)R S , C(═O)OR A , C(═O)N(R D ) 2 , C(═S)R S , C(═S)SR A , C(═S)N(R D ) 2 , C(═NR D )R S ,
phenyl unsubstituted or substituted with up to 5 R E ;
a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO, SO 2 , wherein the aforementioned ring is unsubstituted or substituted with up to 5 R E , or
two R i on one nitrogen atom are together a C 2 -C 7 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO, SO 2 , and wherein the alkylene chain is unsubstituted or substituted with halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl;
each R m is independently selected from the group consisting of hydrogen, —SCN, SF 5 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R M ;
Si(R e ) 3 , OR A , SR A , OSO 2 R B , N(R D ) 2 , C(═O)N(R D ) 2 , C(═S)N(R D ) 2 , C(═O)OR A , phenyl unsubstituted or substituted with up to 5 R E ;
a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO 2 , wherein the aforementioned ring is unsubstituted or substituted with up to 5 R E ;
each R A is independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 alkoxy;
phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 haloalkoxy and (C 1 -C 6 -alkoxy)carbonyl;
each R B is independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 alkoxy;
phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 haloalkoxy and (C 1 -C 6 -alkoxy)carbonyl;
each R D is independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 -alkoxy;
phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 haloalkoxy and (C 1 -C 6 -alkoxy)carbonyl, or
two R D on one nitrogen atom are together a C 2 -C 6 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO, SO 2 , and wherein the alkylene chain is unsubstituted or substituted with halogen, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
each R E is independently selected from the group consisting of cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 -alkoxy, or
two R E present on one atom of a saturated or partially unsaturated heterocyclic ring are together ═O, ═N(C 1 -C 6 -alkyl), ═NO(C 1 -C 6 -alkyl), ═CH(C 1 -C 4 -alkyl) or ═C(C 1 -C 4 -alkyl)C 1 -C 4 -alkyl;
each R F is independently selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 6 cycloalkyl, C 1 -C 4 alkoxyalkyl, phenyl and benzyl;
each R G is independently selected from the group consisting of halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, C 1 -C 6 haloalkoxyalkyl;
each R H is independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 alkoxy;
each R J is independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 alkoxy;
each R K is independently selected from the group consisting of hydrogen, cyano, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 -alkoxy;
each R L is independently C 1 -C 4 alkyl or C 1 -C 4 alkoxyalkyl;
each R M is independently selected from the group consisting of halogen, cyano, azido, nitro, OH, SH, —SCN, SF 5 , C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 1 -C 6 -alkyl-C 3 -C 8 -cycloalkyl, wherein the five last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 alkoxy, or
two R M present on one carbon atom are together ═O, ═CH(C 1 -C 4 -alkyl), ═C(C 1 -C 4 -alkyl)C 1 -C 4 -alkyl, ═N(C 1 -C 6 -alkyl) or ═NO(C 1 -C 6 -alkyl);
each R N is independently selected from the group consisting of hydrogen, OH, SH, —SCN, SF 5 , C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, wherein the three last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 alkoxy;
each R Q is independently selected from the group consisting of hydrogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 alkoxy;
phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 haloalkoxy and (C 1 -C 6 -alkoxy)carbonyl;
each R S is independently selected from the group consisting of hydrogen, OH, SH, —SCN, SF 5 , C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylthio, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl,
C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C 1 -C 4 alkoxy;
phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 haloalkoxy, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino;
p is 0 or 1;
x is 1 or 2,
with the proviso that the following compound is excluded:
3 . The compound of claim 2 , wherein
each R 5 , R 6 is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, SF 5 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R a ; C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkenyl, wherein the carbon atoms of the aforementioned cycloaliphatic radicals are unsubstituted or substituted with one or more R b ; phenyl unsubstituted or substituted with up to 5 R c ; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO, SO 2 , wherein the aforementioned ring is unsubstituted or substituted with up to 5 R d ; Si(R e ) 3 , OR f , SR f , OS(O) x R h , S(O) x R h , N(R) 2 , N(R i )C(═O)R m , OC(═O)R m , C(═O)R m , C(═O)OR f , C(═NR i )R m , C(═S)R m ; or two R 5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of CH 2 CH 2 CH 2 CH 2 , N═CH—CH═CH, CH═N—CH═CH, N═CH—N═CH, OCH 2 CH 2 CH 2 , OCH═CHCH 2 , CH 2 OCH 2 CH 2 , OCH 2 CH 2 O, OCH 2 OCH 2 , CH 2 CH 2 CH 2 , CH═CHCH 2 , CH 2 CH 2 O, CH═CHO, CH 2 OCH 2 , CH 2 C(═O)O, C(═O)OCH 2 , O(CH 2 )O, SCH 2 CH 2 CH 2 , SCH═CHCH 2 , CH 2 SCH 2 CH 2 , SCH 2 CH 2 S, SCH 2 SCH 2 , CH 2 CH 2 S, CH═CHS, CH 2 SCH 2 , CH 2 C(═S)S, C(═S)SCH 2 , S(CH 2 )S, CH 2 CH 2 NR K , CH 2 CH═N, CH═CH—NR K , OCH═N, SCH═N and form together with the carbon atoms the two R 5 are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of ═O, OH, CH 3 , OCH 3 , halogen, halomethyl and halomethoxy.
4 . The compound of claim 2 , wherein
Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R 5 ; or naphthyl unsubstituted or substituted with 1 or 2 substituents R 5 ; Q is a 6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2, 3 or 4 substituents R 6 ; R 1 is selected from the group consisting of H, halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and (C 1 -C 6 -alkoxy)carbonyl, wherein the five radicals last mentioned are unsubstituted or substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, hydroxy, OSi(C 1 -C 6 -alkyl) 3 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and (C 1 -C 6 -alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R 2 is H or halogen; or R 1 and R 2 form together with the carbon atom to which they are attached a methylene group; R 3 is selected from the group consisting of H, halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and (C 1 -C 6 -alkoxy)carbonyl, wherein the five radicals last mentioned are unsubstituted or substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, hydroxy, OSi(C 1 -C 6 -alkyl) 3 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and (C 1 -C 6 -alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R 4 is H or halogen; or R 3 and R 4 form together with the carbon atom to which they are attached a methylene group; R 5 is selected from the group consisting of halogen, cyano, SF 5 , tri-(C 1 -C 4 )silyl-C 2 -C 4 -alkynyl, (C 1 -C 6 -alkyl)aminocarbonyl, di-(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)amino, di-(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkyl)carbonyl and (C 1 -C 6 -alkyl)carbonyloxy, wherein the 14 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, cyano, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and C 1 -C 6 -alkoxy, wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; or two R 5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of N═CH—CH═CH, N═CH—CH═N, OCH 2 CH 2 O, O(CH 2 )O and form together with the carbon atoms the two R 5 are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted; R 6 is selected from the group consisting of halogen, cyano, SF 5 , tri-(C 1 -C 4 )silyl-C 2 -C 4 -alkynyl, (C 1 -C 6 -alkyl)aminocarbonyl, di-(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)amino, di-(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkyl)carbonyl and (C 1 -C 6 -alkyl)carbonyloxy, wherein the 14 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, cyano, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and C 1 -C 6 -alkoxy, wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; p is 0 or 1.
5 . The compound of claim 2 , wherein
Y is phenyl unsubstituted or substituted with 1, 2, 3 or 4 substituents R 5 ; or naphthyl unsubstituted or substituted with 1 or 2 substituents R 5 ; Q is a 6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2, 3 or 4 substituents R 6 ; R 1 is selected from the group consisting of H, halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and (C 1 -C 6 -alkoxy)carbonyl, wherein the five radicals last mentioned are unsubstituted or substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, hydroxy, OSi(C 1 -C 6 -alkyl) 3 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and (C 1 -C 6 -alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R 2 is H or halogen; or R 1 and R 2 form together with the carbon atom to which they are attached a methylene group; R 3 is selected from the group consisting of H, halogen, cyano, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and (C 1 -C 6 -alkoxy)carbonyl, wherein the five radicals last mentioned are unsubstituted or substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, cyano, hydroxy, OSi(C 1 -C 6 -alkyl) 3 , C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy and (C 1 -C 6 -alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R 4 is H or halogen; or R 3 and R 4 form together with the carbon atom to which they are attached a methylene group; R 5 is selected from the group consisting of halogen, cyano, SF 5 , tri-(C 1 -C 4 )silyl-C 2 -C 4 -alkynyl, (C 1 -C 6 -alkyl)aminocarbonyl, di-(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)amino, di-(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkyl)carbonyl and (C 1 -C 6 -alkyl)carbonyloxy, wherein the 14 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, cyano, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and C 1 -C 6 -alkoxy, wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; R 6 is selected from the group consisting of halogen, cyano, SF 5 , tri-(C 1 -C 4 )silyl-C 2 -C 4 -alkynyl, (C 1 -C 6 -alkyl)aminocarbonyl, di-(C 1 -C 6 -alkyl)aminocarbonyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, (C 1 -C 6 -alkoxy)carbonyl, (C 1 -C 6 -alkyl)amino, di-(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkyl)carbonyl and (C 1 -C 6 -alkyl)carbonyloxy, wherein the 14 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, cyano, C 1 -C 4 -alkyl-C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and C 1 -C 6 -alkoxy, wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; p is 0 or 1.
6 . The compound of claim 2 , wherein
R 1 is selected from the group consisting of H, Me, Et, iPr, cPr, CH 2 CN, CF 3 , CHF 2 , CH 2 F, CH 2 CH 2 F, CH 2 CHF 2 , CH 2 CF 3 , CN, halogen, CH 2 OH, CH 2 OMe, CH 2 OEt, CO 2 Me, CO 2 Et, CH 2 CO 2 Me, CH 2 CO 2 Et, CH 2 OSi(Me) 3 and CH 2 OSi(Et) 3 .
7 . The compound of claim 2 , wherein
R 3 is selected from the group consisting of H, Me, Et, iPr, cPr, CH 2 CN, CF 3 , CHF 2 , CH 2 F, CH 2 CH 2 F, CH 2 CHF 2 , CH 2 CF 3 , CN, halogen, CH 2 OH, CH 2 OMe, CH 2 OEt, CO 2 Me, CO 2 Et, CH 2 CO 2 Me, CH 2 CO 2 Et, CH 2 OSi(Me) 3 and CH 2 OSi(Et) 3 .
8 . The compound of claim 2 , wherein
R 5 is selected from the group consisting of halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF 3 , OCF 3 , SF 5 , CHF 2 , OCHF 2 , SMe, S(O)Me, S(O) 2 Me, SCF 3 , S(O)CF 3 , S(O) 2 CF 3 , SCHF 2 , S(O)CHF 2 , S(O) 2 CHF 2 , CO 2 Me, CO 2 Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe 2 , CH 2 OMe and CH 2 OEt; or two R 5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of N═CH—CH═CH, N═CH—CH═N, OCH 2 CH 2 O, O(CH 2 )O and form together with the carbon atoms the two R 5 are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted.
9 . The compound of claim 2 , wherein
R 5 is selected from the group consisting of halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF 3 , OCF 3 , SF 5 , CHF 2 , OCHF 2 , SMe, S(O)Me, S(O) 2 Me, SCF 3 , S(O)CF 3 , S(O) 2 CF 3 , SCHF 2 , S(O)CHF 2 , S(O) 2 CHF 2 , CO 2 Me, CO 2 Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe 2 , CH 2 OMe and CH 2 OEt.
10 . The compound of claim 2 , wherein
R 6 is selected from the group consisting of halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF 3 , OCF 3 , SF 5 , CHF 2 , OCHF 2 , SMe, S(O)Me, S(O) 2 Me, SCF 3 , S(O)CF 3 , S(O) 2 CF 3 , SCHF 2 , S(O)CHF 2 , S(O) 2 CHF 2 , CO 2 Me, CO 2 Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe 2 , CH 2 OMe and CH 2 OEt.
11 . The compound of claim 2 , wherein
Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R 5 ; or naphthyl unsubstituted or substituted with 1 substituent R 5 ; Q is a 6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2 or 3 substituents R 6 ; R 1 is selected from the group consisting of H, Me, Et, CN, CH 2 CN, CH 2 CF 3 , halogen, CH 2 OH, CH 2 OMe, CH 2 OEt, CH 2 CO 2 Me, CH 2 CO 2 Et, CH 2 OSi(Me) 3 and CH 2 OSi(Et) 3 ; R 2 is H or halogen; R 3 is selected from the group consisting of H, Me, Et, CN, CH 2 CN, CH 2 CF 3 , halogen, CH 2 OH, CH 2 OMe, CH 2 OEt, CH 2 CO 2 Me, CH 2 CO 2 Et, CH 2 OSi(Me) 3 and CH 2 OSi(Et) 3 ; R 4 is H or halogen; R 5 is selected from the group consisting of halogen, cyano, tri-(C 1 -C 4 )silyl-C 2 -C 4 -alkynyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio or (C 1 -C 6 -alkoxy)carbonyl, wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; or two R 5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of N═CH—CH═CH, N═CH—CH═N, OCH 2 CH 2 O, O(CH 2 )O and form together with the carbon atoms the two R 5 are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted; R 6 is selected from the group consisting of halogen, cyano, tri-(C 1 -C 4 )silyl-C 2 -C 4 -alkynyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio and (C 1 -C 6 -alkoxy)carbonyl, wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; p is 0 or 1.
12 . The compound of claim 2 , wherein
Y is phenyl unsubstituted or substituted with 1, 2 or 3 substituents R 5 ; or naphthyl unsubstituted or substituted with 1 substituent R 5 ; Q is a 6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2 or 3 substituents R 6 ; R 1 is selected from the group consisting of H, Me, Et, CN, CH 2 CN, CH 2 CF 3 , halogen, CH 2 OH, CH 2 OMe, CH 2 OEt, CH 2 CO 2 Me, CH 2 CO 2 Et, CH 2 OSi(Me) 3 and CH 2 OSi(Et) 3 ; R 2 is H or halogen; R 3 is selected from the group consisting of H, Me, Et, CN, CH 2 CN, CH 2 CF 3 , halogen, CH 2 OH, CH 2 OMe, CH 2 OEt, CH 2 CO 2 Me, CH 2 CO 2 Et, CH 2 OSi(Me) 3 and CH 2 OSi(Et) 3 ; R 4 is H or halogen; R 5 is selected from the group consisting of halogen, cyano, tri-(C 1 -C 4 )silyl-C 2 -C 4 -alkynyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio and (C 1 -C 6 -alkoxy)carbonyl, wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; R 6 is selected from the group consisting of halogen, cyano, tri-(C 1 -C 4 )silyl-C 2 -C 4 -alkynyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio and (C 1 -C 6 -alkoxy)carbonyl, wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; p is 0 or 1.
13 . The compound of claim 2 , wherein
R 5 is selected from the group consisting of halogen, Me, OMe, CN, CF 3 , OCF 3 and ethynyl.
14 . The compound of claim 2 , wherein
R 6 is selected from the group consisting of halogen, Me, OMe, CN, CF 3 , OCF 3 and ethynyl.
15 . The compound of claim 2 , wherein
Y is phenyl unsubstituted or substituted with 1, 2 or 3 substituents R 5 ; Q is pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, wherein the aforementioned rings are unsubstituted or substituted with 1 or 2 substituents R 6 ;
R 1 is selected from the group consisting of H, F, Me, Et, CN, CH 2 CN and CH 2 OMe;
R 2 is H;
R 3 is selected from the group consisting of H, F, Me, Et, CN, CH 2 CN and CH 2 OMe;
R 4 is H;
R 5 is selected from the group consisting of F, Cl, CN, ethynyl, Me, OMe and CF 3 ;
R 6 is F, ethynyl, Br or CF 3 ; p is 0 or 1.
16 . The compound of claim 2 , wherein R 1 is H.
17 . The compound of claim 2 , wherein R 3 is H.
18 . The compound of claim 2 , wherein p is 0.
19 . The compound of claim 2 , wherein Q is pyridyl or pyrimidinyl, wherein the aforementioned rings are unsubstituted or substituted with one or more R 6 .
20 . The compound of claim 2 , wherein R 1 and R 2 are H; and p is 0.
21 . An agricultural and/or veterinary composition comprising at least one compound of formula (I) of claim 2 or a salt or N-oxide thereof.
22 . The composition of claim 21 , further comprising at least one inert liquid and/or at least one solid carrier.Join the waitlist — get patent alerts
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