WO2016113271A1 - Composés imidazoisoquinoléine, compositions comprenant les composés et leur utilisation pour lutter contre des organismes nuisibles invertébrés - Google Patents

Composés imidazoisoquinoléine, compositions comprenant les composés et leur utilisation pour lutter contre des organismes nuisibles invertébrés Download PDF

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WO2016113271A1
WO2016113271A1 PCT/EP2016/050496 EP2016050496W WO2016113271A1 WO 2016113271 A1 WO2016113271 A1 WO 2016113271A1 EP 2016050496 W EP2016050496 W EP 2016050496W WO 2016113271 A1 WO2016113271 A1 WO 2016113271A1
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xyz
alkyl
alkoxy
radicals
group
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Arun Narine
Wolfgang Von Deyn
Joachim Dickhaut
Jean-Yves WACH
Sunderraman SAMBASIVAN
Devendra VYAS
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • Imidazoisoquinoline compounds compositions comprising the compounds and their use for controlling invertebrate pests
  • the present invention relates to novel pesticide imidazoisoquinoline compounds and related azoloisoquinoline compounds which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes.
  • the invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
  • Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an on-going need for new agents for combating invertebrate pests, in particular insects, arachnids and nematodes.
  • WO 2009/102736 describes linear triaryls having a rhamnose type radical which is bound to a terminal aryl group via a bivalent linker such as (thio)carbamate or iminoxy linker. Similar compounds are known from WO 2012/027521.
  • WO 201 1/017504 describes linear triaryls having a methyliden(thio)carbazone motive that carries a (het)aryl or (het)arylalkyl radical.
  • WO 201 1/017513 describe linear triaryls having a carbamate or thiocarbamate motive that carries a (het)arylalkyl radical.
  • WO 2014/204622 describes linear triaryls having a rhamnose carbamate radical.
  • the invention relates to compounds of formula I
  • a 1 is N or C(R 2 ),
  • a 2 is N or C(R 3 );
  • a 3 is N or C(R 4 );
  • a 4 is N or C(R 5 );
  • a 5 is N or C(R 6 );
  • R 2 , R 3 independently of each other, are selected from the group consisting of H, halogen, N 3 , OH, CN, N0 2 , -SCN, -SF 5 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloal- koxy, C2-C6-alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C1-C6- alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3- C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi,
  • R 4 , R 5 , R 6 is selected from the group consisting of H, halogen, N 3 , OH, CN, NO2, -SCN, -SF 5 , Ci-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 2 -C 6 -alkenyl, tri-Ci-C 6 -al- kylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6-cycloal- kyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxyx-Ci-C4-alkyl, where the alkyl, cycloalkyi,
  • one radical may also be phenyl, phenoxy, phenylcarbonyl, phenylthio or benzyl, where the phenyl ring in the last 5 radicals is unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R f ;
  • Ar is phenyl or 5- or 6-membered hetaryl, which are unsubstituted or carry 1 , 2, 3 or 4 radi- cals R Ar , which are identical or different, where
  • R Ar independently of each other, are selected from the group consisting of halogen, N 3 , OH, CN, N0 2 , -SCN, -SF 5 , d-Ce-alkyl, C C 6 -haloalkyl, C C 6 -alkoxy, Ci-C 6 -haloalkoxy, C 2 -C 6 - alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4- alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloal- koxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and
  • n 0, 1 or 2;
  • R Q1 , R Q2 independently of each other are selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6- cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloal- koxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, C(0)-OR a , NR b R
  • R Q3a , R Q3b independently of each other, are selected from the group consisting of H, halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci- C 4 -haloalkylthio;
  • R Q4a , R Q4b independently of each other, are selected from the group consisting of H, halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci- C4-haloalkylthio;
  • R 1 is a moiety of the formula -T-X 1 -Y-Z 1 -R 11 or a moiety -T-X 2 -Y-Z 2 -R 12 , where
  • R 11 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cyclo- alkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cy- cloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated,
  • # indicates the point of attachment to Z 2 ;
  • R 121 , R 122 , R 123 independently of each other are selected from the group consisting of H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkylcarbonlyoxy, Ci-C6-haloalkylcarbonlyoxy, Ci-C6-alkenylcarbonlyoxy, C3- C6-cycloalkylcarbonlyoxy and NR b R c , or one of R 121 , R 122 , R 123 may also be oxo;
  • R 124 is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C4-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and C2-C6-alkenyloxy;
  • T is selected from a single bond, (CHR xa ) s with s being 1 , 2, 3 or 4, cyclopropane-1 , 1 -diyl or cyclopropane-1 ,2-diyl,
  • Y is a single bond, or one of the bivalent groups
  • Z 2 is O, S or N-R z2 ;
  • R x1 , R x2 independently of each other, are selected from the group consisting of H, Ci-C6-al- kyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloal- kyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, C(0)-OR a , Ci-C 6 -alkylen-NR b R c , Ci-C 6 -alkylen-CN, C(0)-NR b R c , C(0)-R d , S0 2
  • R x3 is selected from the group consisting of H, halogen, CN , Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy- Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloal- koxy-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, Ci-
  • R xa is selected from the group consisting of H , halogen and Ci-C6-alkyl, it being possible for s
  • p O or l ;
  • R R 2 independently of each other, are selected from the group consisting of H , Ci-C6-al- kyl, d-Ce-haloalkyl, C2-Ce-alkenyl, C2-Ce-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, d-Ce-alkoxy-
  • Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, C(0)-OR a , Ci-C6-alkylen-N R b R c , Ci-C 6 -alkylen-CN , C(0)-N R R c , C(0)-R d , S0 2 N R R c , S( 0) m R e , phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R f ;
  • Ry 3 is selected from the group consisting of H , Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci- C6-haloalkoxy, C2-C6-alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, where the alkyl, cycloalkyi and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, C C 6 -alkylen-N R R c , Ci-C 6 -alkylen-CN , C(0)-N R R c ,
  • Ry 4 is selected from the group consisting of H , Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2- C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, C(0)-OR a , Ci-C 6 -alkylen-N R R c , Ci-C 6 -alkylen-CN ,
  • Ry 44 is selected from the group consisting of H , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, C(0)-N R R c , C(O)- R d , phenyl, phenylcarbonyl and benzyl, where the phenyl ring in the last 3 radicals is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals R f ;
  • R z1 , R z2 independently of each other are selected from the group consisting of H , Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogenated, C(0)-OR a , C C 6 -alkylen-N R R c , Ci-C 6 -alkylen-CN ,
  • R z3 , R z6 independently of each other, are selected from the group consisting of H, CN, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals R f ;
  • R z4 , R z5 independently of each other, are selected from the group consisting of H, Ci-C6-al- kyl, Ci-C6-haloalkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, Ci-C6-alkoxy-CrC4-alkyl, C3-C6-cycloal- kyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or par- tially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carries 1 , 2, 3, 4 or 5 radicals R f ;
  • R y4 together with R z6 may also form a linear Ci-C6-alkylene group or a linear C2-C6-alkenylene group, where in the linear Ci-C6-alkylene group and the linear C2-C6-alkenylene group a
  • R is selected from the group consisting of H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy- Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloal- koxy-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, Ci-C 6 -
  • each m is independently 0, 1 or 2;
  • each R a is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4- alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogen- ated, Ci-C6-alkylen-NR b R c , Ci-C6-alkylen-CN, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R
  • each R b is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4- alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogen- ated, Ci-C6-alkylen-CN, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R f ;
  • each R c is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-CrC4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4- alkyl, C3-C6-cycloalkoxy-CrC4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogen- ated, Ci-C6-alkylen-CN, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R f ;
  • each R d is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4- alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 4 mentioned radicals are unsubstituted or partially or completely halogen- ated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R f ;
  • each R e is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloal- kyl, C3-C6-cycloalkyl-Ci-C4-alkyl, where the alkyl and cycloalkyl parts of the last 2 mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R f ;
  • each R f is selected from the group consisting of halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3- C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxyx-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstit
  • each R9 is selected from the group consisting of halogen, N3, OH, CN, NO2, -SCN, -SF5, Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3- C6-cycloalkoxy, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the al- kyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubsti-
  • each R hh is selected from halogen, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, or CN;
  • the present invention also relates to a compound of the formula INT and to the tautomers and salts thereof
  • T is selected from a single bond, (CHR xa ) s with s being 1 , 2, 3 or 4, cyclopropane-1 ,1 -diyl or cyclopropane-1 ,2-diyl,
  • R x1a is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2- Ce-alkynyl, Ci-C 6 -alkoxy-Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C 4 -alkyl, C 3 -C 6 - cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, Ci- C6-alkylen-NR b R c , Ci-C6-alkylen-CN, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2,
  • R x3a is selected from the group consisting of H, OH, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, tri-Ci-C6-alkylsilyl, C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C4-al- kyl, Ci-C6-alkoxy-Ci-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C3-C6-cycloalkoxy-Ci- C4-alkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last 6 mentioned radicals are unsubstituted or partially or completely halogenated, Ci-C 6
  • R xa , A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , C 1 , C 2 and Q are as defined in formula I and the salts thereof.
  • the present invention also relates to and includes the following aspects: an agricultural composition comprising at least one compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or an agriculturally acceptable salt thereof, and at least one liquid and/or solid carrier.
  • a veterinary composition comprising at least one compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or a verterinarily acceptable salt thereof, and at least one liquid and/or solid carrier.
  • a method for combating or controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesti- cidally effective amount of a compound selected from compounds of formula I, the N-oxides, stereoisomers, tautomers or salts thereof as defined herein.
  • a method for protecting growing plants from attack or infestation by invertebrate pests comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or an agriculturally or veterinarily acceptable salt thereof, or a composition as defined herein.
  • a method for the protection of plant propagation material, more particularly seeds, from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the plant propagation material respectively seeds before sowing and/or after pre-germina- tion with at least one compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or an agriculturally or veterinarily acceptable salt thereof, or a composition as defined herein, plant propagation material, in particular seed, comprising at least one compound of formula I, an N-oxide, a stereoisomer, a tautomer and/or an agriculturally acceptable salt thereof as defined herein.
  • a method for treating a non-human animal infested or infected by parasites or for preventing a non-human animal from getting infested or infected by parasites or for protecting a non-human animal against infestation or infection by parasites which comprises orally, topically or parenteraly administering or applying to the non-human animal a parasiticidally effective amount of a compound compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or a veterinarily acceptable salt thereof or a composition as defined in claim herein.
  • a compound compound of formula (I) or a stereoisomer, a tautomer, a N-oxide or a veterinar- ily acceptable salt thereof for use as a medicament.
  • tautomers encompasses isomers, which are derived from the compounds of formula I by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom.
  • tautomeric forms are keto-enol forms, imine-enamine forms, urea- isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.
  • stereoisomers encompasses both optical isomers, such as enantiomers or dia- stereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastere- omers.
  • One center of chirality is the carbon ring atom of the isothiazoline ring carrying radical R 1 .
  • the invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures.
  • Suitable compounds of the formula I also include all possible geometrical stereoi- somers (cis/trans isomers) and mixtures thereof.
  • N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO). To be more precise, it relates to any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • N- oxides of compounds I can in particular be prepared by oxidizing e.g. the ring nitrogen atom of an N-heterocycle, e.g. a pyridine or pyrimidine ring present in Ar or R 11 , or an imino-nitrogen present in central tricyclic core, with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides.
  • a suitable oxidizing agent such as peroxo carboxylic acids or other peroxides.
  • the compounds of the present invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have a different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the formula I are preferably agriculturally and veterinarily ac- ceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
  • Suitable agriculturally acceptable salts are more particularly the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH 4+ ) and substituted ammonium in which one to four of the H atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, CrC 4 -alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-CrC 4 -alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, dime- thylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetrae- thylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyeth- oxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyl-tri- ethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sul- fonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, H sulfate, sulfate, diH phosphate, H phosphate, phosphate, nitrate, H carbonate, carbonate, hexafluorosili- cate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formu- lae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Suitable acid addition salts e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
  • inorganic acids for example hydrochlorides, sulphates, phosphates, and nitrates
  • salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
  • invertebrate pest encompasses animal populations, such as in- sects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
  • the plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting. Said young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • plants comprises any types of plants including “non-cultivated plants” and in particular "cultivated plants”.
  • non-cultivated plants refers to any wild type species or related species or re- lated genera of a cultivated plant.
  • cultiva plants is to be understood as including plants which have been modi- tied by breeding, mutagenesis or genetic engineering including but not limiting to agricultural bi- otech products on the market or in development (cf.
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that un- der natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
  • herbicides e. bromoxynil or ioxynil herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • ALS inhibitors e.g. described in Pest Managem. Sci.
  • cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, more particularly those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as ⁇ -endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • VIP1 , VIP2, VIP3 or VIP3A vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins pro- prised by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid- IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium
  • insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278,
  • WO 95/34656 EP-A 427 529, EP-A 451 878, WO 03/18810, and WO 03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
  • These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, more particularly to beetles (Coe- loptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called "path- ogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora in- festans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins path- ogenesis-related proteins
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora in- festans derived from the mexican wild potato Solanum bulbocastanum
  • T4-lysozym e
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
  • plants are also covered that contain by the use of recombinant DNA tech- niques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada).
  • recombinant DNA tech- niques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA tech- niques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato, BASF SE, Germany).
  • recombinant DNA tech- niques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato, BASF SE, Germany).
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n - Cm indicates in each case the possible number of carbon atoms in the group.
  • halogen denotes in each caseF,Br,CI orl, in particularF,CI orBr.
  • partially or fully halogenated will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the H atoms of a given radical have been replaced by a halogen atom, in particular byF orCI.
  • a partially or fully halogenated radical is termed below also “halo-radical”.
  • partially or fully halogenated alkyl is also termed haloalkyl
  • partially or fully halogenated cy- cloalkyl is also termed halocycloalkyl
  • partially or fully halogenated alkylenyl is also termed haloalkenyl
  • partially or fully halogenated alkylynyl is also termed haloalkynyl
  • partially or fully halogenated cycloalkylalkyl is also termed halocycloalkylalkyl.
  • alkyl as used herein and in the alkyl moieties of alkoxy, alkylthio, and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 (“Ci-C2-alkyl"), 1 to 3 (“Ci-C 3 -alkyl"),1 to 4 (“Ci-C 4 -alkyl”) or 1 to 6 (“Ci-C 6 -alkyl”) carbon atoms.
  • Ci-C 2 -Alkyl is CH3I or C2H5.
  • Ci-C3-Alkyl is additionally propyl and isopropyl.
  • Ci-C 4 -Alkyl is additionally butyl, 1- methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1 ,1-dimethylethyl (tert-butyl).
  • Ci-C6-Alkyl is additionally also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethyl- propyl, 1 -ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methyl- pentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbuty
  • haloalkyl refers to straight-chain or branched alkyl groups having 1 to 2 (“Ci-C2-haloal- kyl”), 1 to 3 (“Ci-C 3 -haloalkyl”), 1 to 4 (“Ci-C 4 -haloalkyl”) or 1 to 6 (“Ci-C 6 -haloalkyl”) carbon atoms (as mentioned above), where some or all of the H atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromo- methyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluo- romethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1
  • Ci-C3-haloalkyl is additionally, for example, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1 ,1-difluoropropyl, 2,2- difluoropropyl, 1 ,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trifluoroprop-2-yl, 3-chloropropyl and the like.
  • Examples for Ci-C4-haloalkyl are, apart those mentioned for Ci-C3-haloalkyl, 4-chlorobutyl and the like.
  • Halomethyl is CH3 in which 1 , 2 or 3 of the H atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
  • alkylene (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one H atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • Alkylene has preferably 1 to 6 carbon atoms (Ci-C6-alkylene), 2 to 6 carbon atoms (C2-C6-alkylene), in particular 1 to 4 carbon atoms (C1-C4- alkylene) or 2 to 4 carbon atoms (C2-C4-alkylene).
  • alkylene examples include methylene (CH2), 1 ,1 -ethandiyl, 1 ,2-ethandiyl, 1 ,3-propandiyl, 1 ,2-propandiyl, 2,2-propandiyl, 1 ,4-butandiyl, 1 ,2- butandiyl, 1 ,3-butandiyl, 2,3-butandiyl, 2,2-butandiyl, 1 ,5-pentandiyl, 2,2-dimethylpropan-1 ,3-diyl, 1 ,3-dimethyl-1 ,3-propandiyl, 1 ,6-hexandiyl etc.
  • CH2 methylene
  • alkylene examples include methylene (CH2), 1 ,1 -ethandiyl, 1 ,2-ethandiyl, 1 ,3-propandiyl, 1 ,2-propandiyl, 2,2-propandiyl, 1 ,4-
  • alkenyl refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C 2 -C 3 -alkenyl"), 2 to 4 (“C 2 -C 4 -alkenyl") or 2 to 6 (“C 2 -C 6 - alkenyl) carbon atoms and a double bond in any position, for example C2-C3-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl or 1 -methylethenyl; C2-C 4 -alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1- propenyl, 1 -methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such
  • haloalkenyl as used herein, which is also expressed as “alkenyl which is partially or fully halogenated”, refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C 2 -C 3 -haloalkenyl"), 2 to 4 (“C 2 -C 4 -haloalkenyl”) or 2 to 6 (“C 2 -C 6 -haloalkenyl”) carbon atoms and a double bond in any position (as mentioned above), where some or all of the H atoms in these groups are replaced by halogen atoms as mentioned above, in particularF,CI andBr, for example chlorovinyl, chloroallyl and the like.
  • alkynyl refers to straight-chain or branched hydrocarbon groups having 2 to 3 (“C 2 -C 3 -alkynyl”), 2 to 4 (“C 2 -C 4 -alkynyl”) or 2 to 6 (“C 2 -C 6 -alkynyl”) carbon atoms and one or two triple bonds in any position, for example C 2 -C3-alkynyl, such as ethynyl,
  • C 2 -C 4 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl and the like, C 2 -C6-alkynyl, such as ethynyl, 1-propynyl,
  • haloalkynyl as used herein, which is also expressed as “alkynyl which is partially or fully halogenated”, refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 ("C 2 -C 3 -haloalkynyl"), 2 to 4 ("C 2 -C 4 -haloalkynyl"), 3 to 4 ("C 3 -C 4 -haloalkynyl”) or 2 to 6 (“C 2 -C6-haloalkynyl”) carbon atoms and one or two triple bonds in any position (as mentioned above), where some or all of the H atoms in these groups are replaced by halogen atoms as mentioned above, in particularF,CI andBr;
  • cycloalkyi refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having in particular 3 to 6 (“C3-C6-cycloalkyl") or 3 to 5 (“Cs-Cs-cycloalkyl”) or 3 to 4 (“C3-C 4 -cycloalkyl”) carbon atoms.
  • Examples of monocyclic radicals having 3 to 4 carbon atoms comprise cyclopropyl and cyclobutyl.
  • monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl.
  • Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclo- pentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1 ]heptyl, bicyclo[3.1.1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]- octyl.
  • the term cycloalkyi denotes a monocyclic saturated hydrocarbon radical.
  • cycloalkoxy refers to a cycloalkyi radical, in particular a monocyclic cycloalkyi radical, as defined above having in particular 3 to 6 (“C3-C6-cycloalkoxy”) or 3 to 5 (“C3-C5-cycloalkoxy”) or 3 to 4 (“C3-C 4 -cycloalksoxy”) carbon atoms, which is bound via an oxygen atom to the remainder of the molecule.
  • halocycloalkyl as used herein, which is also expressed as “cycloalkyl which is partially or fully halogenated”, refers to mono- or bi- or polycyclic saturated hydrocarbon groups having preferably 3 to 6 ("C 3 -C 6 -halocycloalkyl") or 3 to 5 (“C 3 -C 5 -halocycloalkyl”) or 3 to 4 (“C 3 - C4-halocycloalkyl”) carbon ring members (as mentioned above) in which some or all of the H at- oms are replaced by halogen atoms as mentioned above, in particularF,CI andBr.
  • cycloalkyl-Ci-C4-alkyl refers to a Cs-Cs-cycloalkyl group ("Cs-Cs-cycloalkyl-Ci- C4-alkyl”), preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-Ci-C4-alkyl”), more preferably a C3-C4-cycloalkyl group (“C3-C4-cycloalkyl-Ci-C4-alkyl”) as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Examples for C3-C4-cycloalkyl-Ci-C4-alkyl are cyclopropylmethyl, cyclopropyl- ethyl, cyclopropyl propyl, cyclobutylmethyl, cyclobutylethyl and cyclobutylpropyl
  • Examples for C3-C6-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C4-cycloalkyl-Ci-C4-alkyl, are cyclo- pentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclo- hexylpropyl.
  • C3-C6-halocycloalkyl-Ci-C4-alkyl refers to a Cs-Cs-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • C3-C6-cycloalkxoy-Ci-C4-alkyl refers to a C3-C6-cycloalkoxy group ("Cs-Cs-cy- cloalkoxy-Ci-C4-alkyl”), as defined above (preferably a monocyclic cycloalkoxy group) which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Examples for C3-C4-cycloalkoxy-Ci-C4-alkyl are cyclopropyloxymethyl, cyclopropyloxyethyl, cyclopropyloxy- propyl, cyclobutyloxymethyl, 1-cyclobutyloxyethyl and 2-cyclobutyloxypropyl,
  • Examples for C3- C6-cycloalkoxy-Ci-C4-alkyl, apart those mentioned for C3-C4-cycloalkoxy-Ci-C4-alkyl, are cyclo- pentyloxymethyl, cyclopentyloxyethyl, cyclopentyloxypropyl, cyclohexyloxymethyl, cyclohexylox- yethyl and cyclohexyloxypropyl.
  • Ci-C2-alkoxy is a Ci-C2-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C3-alkoxy is a Ci-C3-alkyl group, as defined above, attached via an oxygen atom.
  • CrC4-alkoxy is a Ci-C4-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C6-alkoxy is a Ci-C6-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-Cio-alkoxy is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • Ci-C3-Alkoxy is additionally, for example, n-prop- oxy and 1 -methylethoxy (isopropoxy).
  • Ci-C4-Alkoxy is additionally, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1-dimethylethoxy (tert-butoxy).
  • Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methyl- butoxy, 1 ,1-dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hex- oxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethyl- butoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1 - methylpropoxy or 1 -ethyl-2-methylpropoxy.
  • d-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
  • Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.
  • the term "Ci-C2-haloalkoxy” is a Ci-C2-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C3-haloalkoxy is a Ci-C3-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C4-haloalkoxy is a Ci-C4-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C6-haloalkoxy is a Ci-C6-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-Cio-haloalkoxy is a Ci-Cio-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C2-Haloalkoxy is, for example, OCH 2 F, OCH F2, OCF3, OCH2CI, OCHC , OCCIs, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluo- roethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro- 2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5.
  • Ci-C3-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3- chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH 2 -C 2 F 5 , OCF 2 -C 2 F 5 , 1 -(CH 2 F)-2-fluoroethoxy, 1-(CH 2 CI)-2-chloroeth- oxy or 1-(CH2Br)-2-bromoethoxy.
  • Ci-C4-Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
  • Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6- fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
  • Ci-C3-alkoxy-Ci-C3-alkyl refers to a straight-chain or branched alkyl group having 1 to 3 carbon atoms, as defined above, where one H atom is replaced by a Ci-C3-alkoxy group, as defined above.
  • Ci-C3-alkoxy-CrC4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one H atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • C1-C6- alkoxy-Ci-C4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one H atom is replaced by a Ci-C6-alkoxy group, as defined above.
  • Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, 1 -methoxyethyl, 1-ethox- yethyl, 1 -propoxyethyl, 1-isopropoxyethyl, 1-n-butoxyethyl, 1 -sec-butoxyethyl, 1-isobutoxyethyl, 1-tert-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butox- yethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1-methoxypropyl, 1 -ethoxypropyl, 1-propoxypropyl, 1 -isopropoxypropyl, 1-n-but
  • Ci-C4-alkoxy-methyl refers to CH3 in which one H atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Ci-C6-alkoxy-methyl refers to CH 3 in which one H atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n- butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert-butoxymethyl, pentyloxymethyl, hex- yloxymethyl and the like.
  • alkoxyalkoxy refers to an alkoxyalkyl radical, in particular a Ci- C6-alkoxy-Ci-C4-alkyl radical, as defined above, which is bound via an oxygen atom to the remainder of the molecule.
  • Examples thereof are OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH(CH 3 )2, n-butoxymethoxy, (l -methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH 2 -OC(CH 3 )3, 2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1 -methyleth- oxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1 ,1 -dimethylethoxy)ethoxy, etc.
  • Ci-C4-Haloalkoxy-CrC4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the H atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining H atoms (either in the alkoxy moiety or in the alkyl moiety or in both) are replaced by halogen atoms.
  • Examples are difluoromethoxyme- thyl (CHF2OCH2), trifluoromethoxymethyl, 1 -difluoromethoxyethyl, 1-trifluoromethoxyethyl, 2- difluoromethoxyethyl, 2-trifluoromethoxyethyl, difluoro-methoxy-methyl (CH3OCF2), 1 ,1 -difluoro- 2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.
  • CHF2OCH2 difluoromethoxyme- thyl
  • trifluoromethoxymethyl 1 -difluoromethoxyethyl
  • 1-trifluoromethoxyethyl 2- difluoromethoxyethyl
  • 2-trifluoromethoxyethyl 2-trifluoromethoxyethyl
  • difluoro-methoxy-methyl CH3OCF2
  • Ci-C2-alkylthio is a Ci-C2-alkyl group, as defined above, attached via a sulfur atom.
  • CrC3-alkylthio is a Ci-C3-alkyl group, as defined above, attached via a sulfur atom.
  • CrC4-alkylthio is a Ci-C4-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-Ce-alkylthio is a Ci-C6-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-Cio-alkylthio is a Ci-Cio-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C2-Alkylthio is methylthio or ethylthio.
  • Ci-C3-Alkylthio is additionally, for example, n- propylthio or 1-methylethylthio (isopropylthio).
  • Ci-C4-Alkylthio is additionally, for example, bu- tylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethyl- thio (tert-butylthio).
  • Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1-dimethylpropylthio, 1 ,2-dimethylpropylthio, 2,2-dime- thylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2-methylpentylthio, 3-methylpen- tylthio, 4-methylpentylthio, 1 ,1-dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthio, 2-ethyl- butylthio,
  • d-Cs-Alkylthio is additionally, for example, heptylthio, octylthio, 2- ethylhexylthio and positional isomers thereof.
  • Ci-Cio-Alkylthio is additionally, for example, nonyl- thio, decylthio and positional isomers thereof.
  • CrC2-haloalkylthio is a Ci-C2-haloalkyl group, as defined above, attached via a sulfur atom.
  • CrC3-haloalkylthio is a Ci-C3-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C4-haloalkylthio is a Ci-C4-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C6-haloalkylthio is a Ci-C6-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-Cio-haloalkylthio is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C2-Haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2CI, SCHC , SCCI3, chlorofluoromethylthio, dichlorofluoromethylthio, chloro- difluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2- difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthi
  • C C 3 -Haloalkylthio is addition- ally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoro- propylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2-C2F5, SCF2-C2F5, 1- (CH 2 F)-2-fluoroethylthio, 1 -(CH 2 CI)-2-chloroethylthio or 1 -(CH 2 Br)-2-bromoethylthio.
  • Ci-C 4 -Halo- alkylthio is additionally, for example, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or no- nafluorobutylthio.
  • Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloro- pentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlo- rohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.
  • aryl relates to phenyl and bi- or polycyclic carbocycles having at least one fused phenylene ring, which is bound to the remainder of the molecule.
  • bi- or polycyclic carbocycles having at least one phenylene ring include naphthyl, tetrahydronaphthyl, inda- nyl, indenyl, anthracenyl, fluorenyl etc.
  • aryl-Ci-C 4 -alkyl relates to Ci-C 4 -alkyl, as defined above, wherein one H atom has been replaced by an aryl radical, in particular a phenyl radical.
  • aryl- CrC 4 -alkyl include benzyl, 1-phenethyl, 2-phenetyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenyl-1 - propyl and 2-phenyl-2-propyl.
  • aryloxy-Ci-C 4 -alkyl relates to Ci-C 4 -alkyl, as defined above, wherein one H atom has been replaced by an aryloxy radical, in particular a phenoxy radical.
  • aryloxy-Ci-C 4 -alkyl include phenoxymethyl, 1 -phenoxyethyl, 2-phenoxyetyl, 1 -phenoxy- propyl, 2-phenoxypropyl, 3-phenoxy-1 -propyl and 2-phenoxy-2-propyl.
  • aryl-Ci-C 4 -carbonyl relates to aryl as defined above, , in particular a phenyl radical, which is bound by a carbonyl group to the remainder of the molecule.
  • arylcarbonyl include benzoyl, 1 -naphthoyl and 2-naphthoyl.
  • hetaryl relates to aromatic heterocycles having either 5 or 6 ring atoms (5- or 6- membered hetaryl) and being monocyclic or 8, 9 or 10 ring atoms and bing bicyclic.
  • Hetaryl will generally have at least one ring atom selected from O, S and N, which in case of N may be an imino-nitrogen or an amino-nitrogen, which carries H or a radical different from H.
  • Hetaryl may have 1 , 2, 3 or 4 further nitrogen atoms as ring members, which are imino nitrogens.
  • Examples of 5- or 6-membered hetaryl include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3- pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2- thiazolyl, 4-thiazolyl, 5-thiazolyl, 1 -imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1-yl, 1 ,3,4- triazol-2-yl, 1 ,3,4-oxadiazolyl-2-yl, 1 ,3,4-thiadiazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyri- dazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,
  • Examples of 8-, 9- or 10-membered hetaryl include, for example, quinolinyl, isoquinolinyl, cinnolinyl, indolyl, indolizynyl, isoindolyl, indazolyl, benzofuryl, benzothienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, benzimidazolyl, imidazo[1 ,2-a]pyridine-2-yl, thieno[3,2-b]pyridine-5- yl, imidazo-[2,1-b]-thiazol-6-yl and 1 ,2,4-triazolo[1 ,5-a]pyridine-2-yl.
  • Examples of N-bound 5-, 6-, 7 or 8-membered saturated heterocycles include: pyrrolidin-
  • hetaryl-Ci-C4-alkyl relates to Ci-C4-alkyl, as defined above, wherein one H atom has been replaced by a hetaryl radical, in particular a pyridyl radical.
  • a hetaryl radical in particular a pyridyl radical.
  • Particular examples of hetaryl-Ci-C4-alkyl include 2-pyridylmethyl, 3-pyridylmethyl, 4-pyridylmethyl, 1 -(2-pyridyl)ethyl,
  • hetaryloxy-Ci-C4-alkyl relates to Ci-C4-alkyl, as defined above, wherein one H atom has been replaced by an hetaryloxy radical, in particular a pyridyloxy radical.
  • hetaryloxy-Ci-C4-alkyl include 2-pyridyloxymethyl, 3-pyridyloxymethyl, 4-pyri- dyloxymethyl, 1 -(2-pyridyloxy)ethyl, 2-(2-pyridyloxy)ethyl, 1 -(3-pyridyloxy)ethyl, 2-(3-pyri- dyloxy)ethyl, 1 -(4-pyridyloxy)ethyl, 2-(4-pyridyloxy)ethyl etc.
  • hetaryl-Ci-C4-carbonyl relates to hetaryl as defined above, in particular a C- bound hetaryl radical, e.g. 2-, 3-or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrimidinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl radical, which is bound by a carbonyl group to the remainder of the molecule.
  • a C- bound hetaryl radical e.g. 2-, 3-or 4-pyridyl, 2- or 3-thienyl, 2- or 3-furyl, 1-, 2- or 3-pyrrolyl, 2- or 4-pyrimidinyl, pyridazinyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4-imidazolyl radical, which is bound by a carbonyl group to the remainder of the molecule.
  • a first group (A) of embodiments of the present invention relates to compounds of the formula (l-A), including their N-oxides, stereoisomers, tautomers and their agriculturally or veteri- narily
  • R 3 is in particular selected from the group consisting of H, halogen, such asF,CI orBr, CN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH 3 , C2H5, n-propyl or isopropyl, Ci-C6-haloalkyl, in particular fluorinated Ci- Cs-alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CF 2 CHF 2 , C 2 F 5 , CH 2 CH 2 CF 3 , CH 2 CF 2 CHF 2 , or CH 2 CF 2 CF 3 .
  • R 3 is H.
  • a second group (B) of embodiments of the present invention relates to compounds of the formula (l-B), including their N-oxides, stereoisomers, tautomers and their agriculturally or veterinary acceptable salts:
  • R 2 is in preferably selected from the group consisting of H, halogen, such asF,CI orBr, CN, Ci-C6-alkyl, in particular Ci-C 3 -alkyl such as CH 3 , C 2 H5, n-propyl or isopropyl, Ci-C6-haloalkyl, in particular fluorinated Ci- Cs-alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CF 2 CHF 2 , C 2 F 5 , CH 2 CH 2 CF 3 , CH 2 CF 2 CHF 2 , or CH2CF2CF3.
  • R 2 is H.
  • a third group (C) of embodiments of the present invention relates to compounds of the formula (l-C), including their N-oxides, stereoisomers, tautomers and their agriculturally or veterinary acceptable salts:
  • Ar, Q, R 1 , R 2 , R 3 , A 3 , A 4 and A 5 are as defined herein and wherein R 2 and R 3 are identical or different and are in particular selected from the group consisting of H, halogen, such asF,CI orBr, CN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, Ci-C6-haloalkyl, in particular fluorinated Ci-C3-alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 ,
  • R 2 and R 3 are is H.
  • a fourth group (D) of embodiments of the present invention relates to compounds of the formula (l-D), including their N-oxides, stereoisomers, tautomers and their agriculturally or veterinary
  • Ar, Q, R 1 , A 3 , A 4 and A 5 are as defined herein.
  • R 4 , R 5 and R 6 are, independently of each other, preferably selected from the group consisting of H, halogen such asF,CI orBr, CN, NO2, SCN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, C1-C6- haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, or CH2CF2CF3, d-Ce-alkoxy, in particular C C 3 -alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloalkoxy, in particular fluorinated Ci- Cs-alkoxy such as OCH 2 F, OCHF
  • R 4 , R 5 and R 6 are, independently of each other, in particular selected from the group consisting of H,F,CI, Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, or C1-C6- haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2 or CH2CF2CF3. More particularly, R 4 , R 5 and R 6 are H.
  • R 5 and R 6 are, independently of each other, preferably selected from the group consisting of H, halogen such asF,CI orBr, CN, NO2, SCN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, C1-C6- haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, or CH2CF2CF3, d-Ce-alkoxy, in particular C C 3 -alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloalkoxy, in particular fluorinated Ci- Cs-alkoxy such as OCH 2 F, OCHF 2 , O
  • R 5 and R 6 are, independently of each other, in particular selected from the group consisting of H,F,CI, Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, or Ci-C6-haloal- kyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH 2 CF 2 CHF 2 or CH2CF2CF3. More particularly, R 5 and R 6 are H.
  • R 4 and R 6 are, independently of each other, preferably selected from the group consisting of H, halogen such asF,CI orBr, CN, NO2, SCN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, C1-C6- haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, or CH2CF2CF3, Ci-Ce-alkoxy, in particular Ci-C 3 -alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloalkoxy, in particular fluorinated Ci- Cs-alkoxy such as OCH 2 F, OCHF 2 , O
  • R 4 and R 6 are, independently of each other, in particular selected from the group consisting of H,F,CI, Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, or Ci-C6-haloal- kyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH 2 CF 2 CHF 2 or CH2CF2CF3. More particularly, R 4 and R 6 are H.
  • R 4 and R 5 are, independently of each other, preferably selected from the group consisting of H, halogen such asF,CI orBr, CN, NO2, SCN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, C1-C6- haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, or CH2CF2CF3, Ci-Ce-alkoxy, in particular Ci-C 3 -alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloalkoxy, in particular fluorinated Ci- Cs-alkoxy such as OCH 2 F, OCHF 2 , O
  • R 4 and R 5 are, independently of each other, in particular selected from the group consisting of H,F,CI, Ci-C 3 -alkyl such as CH3, ethyl, n-propyl or isopropyl, or Ci-C6-haloal- kyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH 2 CF 2 CHF 2 or CH 2 CF 2 CF 3 . More particularly, R 4 and R 5 are H.
  • R 6 is preferably selected from the group consisting of H, halogen such asF,CI orBr, CN, NO2, SCN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH 3 , C2H5, n-propyl or isopropyl, Ci-C6-haloalkyl, in particular fluorinated Ci-C3-alkyl such as CH2F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, or CH 2 CF 2 CF 3 , Ci-C 6 -alkoxy, in particular Ci-C3-alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloal- koxy, in particular fluorinated Ci-C3-alkoxy such as OCH2F, OCHF2, OCF3, OCH2CF
  • R 6 is in particular selected from the group consisting of H,F,CI, Ci-C3-alkyl such as CH 3 , C2H5, n-propyl or isopropyl, or Ci-C6-haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CF 2 CHF 2 , C 2 F 5 ,
  • R 6 is H.
  • R 5 is preferably selected from the group consisting of H, halogen such asF,CI orBr, CN, NO2, SCN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, Ci-C6-haloalkyl, in particular fluorinated Ci-C3-alkyl such as CH 2 F, CHF2, CF 3 , CH2CF3, CF2CHF2, C 2 F 5 , CH2CH2CF3, CH2CF2CHF2, or CH 2 CF 2 CF 3 , C C 6 -alkoxy, in particular Ci-C3-alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloal- koxy, in particular fluorinated Ci-C3-alkoxy such as OCH2F, OCHF2, OCF3, OCH2CF3,
  • R 5 is in particular selected from the group consisting of H,F,CI, Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, or Ci-C6-haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5,
  • R 5 is H.
  • R 4 is preferably selected from the group consisting of H, halogen such asF,CI orBr, CN, NO2, SCN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, Ci-C6-haloalkyl, in particular fluorinated Ci-C3-alkyl such as CH2F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, or CH2CF2CF3, d-Ce-alkoxy, in particular Ci-C3-alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, CrC6-haloal- koxy, in particular fluorinated Ci-C3-alkoxy such as OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CF 3 , OCH 2 CF 3
  • R 4 is in particular selected from the group consisting of H,F,CI, Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, or Ci-C6-haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5,
  • R 4 is H.
  • Particular groups of embodiments relate to compound of the formulae la, lb, Ic, Id, le, If, Ig, Ih, li, Ij, Ik, Im, In, lo, Ip or Iq, the N-oxides, stereoisomers, tautomers and to the agriculturally or veterinarily acceptable salt thereof:
  • R 2 and R 3 are selected from the group consisting of H, halogen, such asF,CI orBr, CN, Ci-
  • Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl
  • Ci-C6-haloalkyl in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CF 2 CHF 2 , C 2 F 5 ,
  • R 2 and R 3 are is H.
  • R 4 , R 5 and R 6 are, independently of each other, selected from the group consisting of H, halogen such asF,CI orBr, CN, N0 2 , SCN, d-Ce-alkyl, in particular Ci-C 3 -alkyl such as CH 3 , C 2 H5, n-propyl or isopropyl, Ci-C6-haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CF 2 CHF 2 , C 2 F 5 , CH 2 CH 2 CF 3 , CH 2 CF 2 CHF 2 , or CH 2 CF 2 CF 3 , Ci-C 6 -alkoxy, in particular Ci-C 3 -alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloal- koxy, in particular fluorinated Ci-C
  • R 4 , R 5 and R 6 are, independently of each other, in particular selected from the group consisting of H,F,CI, Ci-C 3 -alkyl such as CH 3 , C 2 H5, n-propyl or isopropyl, or Ci-C6-haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CF 2 CHF 2 , C 2 F 5 , CH 2 CH 2 CF 3 , CH 2 CF 2 CHF 2 or CH 2 CF 2 CF 3 . More particu- larly, R 4 , R 5 and R 6 are H.
  • n R Q1 , R Q2 , R Q3 , R Q3a , R Q3b , R Q4 , R Q4a and R Q4b are as defined hereinabove and wherein preferably n is 0, 1 or 2;
  • R Q1 is in particular H, Ci-C4-alkyl, C 3 -C6-cycloalkyl, C 3 -C6-cycloalkymethyl or benzyl, more particularly H or CH 3 ;
  • R Q2 is in particular H, Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkymethyl or benzyl, more particularly H or CH3;
  • R Q3 is in particular H,CI,F, Ci-C4-alkyl or Ci-C4-haloalkyl, and more particularly H;
  • R Q4 is in particular H,CI,F, Ci-C4-alkyl or Ci-C4-haloalkyl, and more particularly H;
  • R Q2a is in particular H, Ci-C4-alkyl or CrC4-haloalkyl, and more particularly H;
  • R Q2b is in particular H, Ci-C4-alkyl or Ci-C4-haloalkyl, and more particularly H;
  • R Q3a is in particular H, Ci-C4-alkyl or Ci-C4-haloalkyl, and more particularly H;
  • R Q3b is in particular H, Ci-C4-alkyl or Ci-C4-haloalkyl, and more particularly H;
  • R Q4a is in particular H, Ci-C4-alkyl or Ci-C4-haloalkyl, and more particularly H;
  • R Q4b is in particular H, Ci-C4-alkyl or Ci-C4-haloalkyl, and more particularly H.
  • a particular group of embodiments of compound of formola (I) relates to the compounds of formulae 1-1 to 1-1 10 as described below, to their N-oxides, their stereoisomers, their tautomers and to the agriculturally or veterinarily acceptable salt thereof.
  • R 1 and R Q2 are as defined above and hereinafter and R Q2 is in particular H, Ci-C4-alkyl, such as CH 3 , C2H5, n-propyl or isopropyl, C3-C6-cycloalkyl such as cyclopropyl, cyclobutyl, or cyclohexyl, Cs- Ce-cycloalkymethyl, such as cyclopropylmethyl, cyclobutylmethyl or cyclopentylmethyl, or benzyl, more particularly H or CH3.
  • the radical Ar is in particular selected from the group consisting of phenyl, pyrimidinyl, pyridazinyl and pyridyl, which are unsubstituted or carry 1 , 2 or 3 radicals R Ar .
  • R Ar is preferably selected from the group consisting of halogen, such asF,CI orBr, OH, CN, NO2, SCN, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, C1-C6- haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, or CH2CF2CF3, Ci-Ce-alkoxy, in particular Ci-C 3 -alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloalkoxy, in particular fluorinated Ci- Cs-alkoxy such as OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CF 3 , OCF 2
  • Ar is preferably selected from the group consisting of phenyl, which carries one radical R Ar in the 4-position, 3-pyridyl and 3-pyridazinyl, which carry one radical R Ar in the 6-position and where phenyl, 3-pyridyl and 3-pyridazinyl may carry 1 or 2 further radicals R Ar .
  • R Ar is preferably selected from the group consisting of halogen, such asF,CI orBr, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH 3 , C2H5, n-propyl or isopropyl, Ci-C6-haloal- kyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CH F2, or CH2CF2CF3, Ci-Ce-alkoxy, in particular Ci-C 3 -alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloalkoxy, in particular fluorinated C1-C3- alkoxy such as OCH 2 F, OCHF 2 , OCF 3 , OCH2CF3, OCF 2 CHF 2 , OC2
  • R e is Ci-C 6 -alkyl, in particular Ci-C 3 -alkyl such as CH3, C2H5, n-propyl or isopropyl, or Ci-C6-haloalkyl, in particular fluorinated Ci-C3-alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CF 2 CHF 2 , C 2 F 5 , CH 2 CH 2 CF 3 , CH 2 CF 2 CHF 2 or CH 2 CF 2 CF 3 .
  • the radical R Ar in the 4-position of phenyl is preferably selected from the group consisting of Ci-C4-haloalkyl, more particularly fluorinated Ci-C3-alkyl such as CH2F, CHF2, CF3, CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, or CH 2 CF 2 CF 3 ; Ci-C 4 -haloalkoxy, more particularly fluorinated Ci-C 3 -alkoxy such as OCH 2 F, OCHF 2 , OCF 3 , OCH2CF3, OCF2CHF2, OC2F5, OCH2CH2CF3, OCH2CF2CHF2, or OCH2CF2CF3, and S-R e , where R e is Ci-C 4 -haloalkyl, more particularly fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F
  • the radical R Ar in the 6-position of 3- pyridyl or 3-pyridazinyl is preferably selected from the group consisting of CrC 4 -haloalkyl, more particularly fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CF 2 CHF 2 , C 2 F 5 ,
  • Ci-C 4 -haloalkoxy more particularly fluorinated Ci- Cs-alkoxy such as OCH 2 F, OCHF 2 , OCF 3 , OCH2CF3, OCF 2 CHF 2 , OC2F5, OCH 2 CH 2 CF 3 , OCH2CF2CHF2, or OCH2CF2CF3, and S-R e , where R e is Ci-C 4 -haloalky, more particularly fluorinated d-Cs-alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH 2 CH 2 CF 3 ,
  • radical R Ar in the 6-position of 3-pyridyl or pyridazinyl and the radical R Ar in the 4-position of phenyl is selected from the group consisting of Ci-C4-haloalkyl, Ci-C4-haloalkoxy and S-R e , where R e is Ci-C4-haloalkyl.
  • the further 1 or 2 radicals R Ar are preferably selected from the group consisting of halogen, such asF,CI orBr, Ci-C3-alkyl such as CH 3 , C2H5, n-propyl or isopropyl, fluorinated d-Cs-alkyl such as CH 2 F, CHF 2 , CF 3 , CH 2 CF 3 , CF 2 CHF 2 , C 2 F 5 , CH 2 CH 2 CF 3 , CH 2 CF 2 CHF 2 , or CH 2 CF 2 CF3, Ci-C3-alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, and fluorinated d-Cs-alkoxy such as OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CF 3 , OCF 2 CHF 2 , OC 2 F 5 , OCH 2 CH 2 CF 3 , OCH 2 CF 2 CHF 2 , OCH 2
  • radicals Ar-1 to Ar-9 summarized in Table A below.
  • T is preferably selected from the group consisting of CHR xa , CH(R xa )CH(R xa ) and cyclopropane-1 ,2-diyl.
  • R xa independently of each other, preferably are selected from the group consisting of H and Ci-C4-allkyl, in particular from the group consisting of H and CH3.
  • R xa is more particularly H.
  • T is in particular selected from the group consisting of a single bond, CH 2 , CH 2 CH 2 and 1 ,2-cycloprandiyl.
  • T is more particularly a single bond.
  • R x2 is preferably selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cyclo- alkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halo- genated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R x2 is in particular H or Ci-C4-alkyl, more particularly H.
  • R x3 is preferably selected from the group con- sisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-CrC 4 -alkyl, C3-C6-cycloalkyl, C3-C6-cyclo- alkyl-Ci-C4-alkyl, where the alkyl, cycloalkyi and alkoxy parts of the last 3 mentioned radicals are unsubstituted or partially or completely halogenated, and phenyl, where the phenyl ring is unsubstituted or carries 1 , 2 or 3 radicals R f .
  • R x3 is in particular H or Ci-C4-alkyl, more particularly H.
  • Y is preferably a single bond.
  • Z 2 is preferably O.
  • the moiety of the formula -T-X 2 -Y-Z 2 - is preferably a group of the formulae XYZ-1 or XYZ-2:
  • R 12 is a radical of the formula (A),
  • R 121 , R 122 , R 123 and R 124 are as defined above and wherein R 121 , R 122 , R 123 and R 124 independently of each other and more particularly in combination preferably have the following meanings:
  • R 121 is Ci-C4-alkoxy, in particular methoxy or ethoxy;
  • R 122 is Ci-C4-alkoxy, such as methoxy or ethoxy, or C3-C4-alkenyloxy, such as allyloxy, with R 122 in particular being methoxy or ethoxy;
  • R 123 is OH, Ci-C4-alkoxy, such as methoxy or ethoxy, or C3-C4-alkenyloxy, such as allyloxy, with R 123 in particular being methoxy or ethoxy;
  • R 124 is Ci-C4-alkyl, such as CH3 or C2H5, or Ci-C4-alkoxy-Ci-C4-alkyl, such as methoxymethyl, ethoxymethyl, 2-methoxyethyl or 2-ethoxyethyl, with R 124 in particular being CH3;.
  • R 12 is in particular a radical of the formula ( ⁇ '), e.g. (A'-a) or (A'-b)
  • R 121 is Ci-C4-alkoxy, in particular methoxy or ethoxy;
  • R 122 is Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxyx or isopropoxy, or C3-C4-alkenyloxy, such as allyloxy, with R 122 in particular being methoxy, ethoxy or n-propoxy;
  • R 123 is OH, Ci-C4-alkoxy, such as methoxy or ethoxy, or C3-C4-alkenyloxy, such as allyloxy, with R 123 in particular being methoxy or ethoxy;
  • R 124 is Ci-C4-alkyl, such as CH 3 or C2H5, or Ci-C4-alkoxy-CrC4-alkyl, such as methoxymethyl, ethoxymethyl, 2-methoxyethyl or 2-ethoxyethyl, with R 124 in particular being CH 3 .
  • radicals R 12 are the following radicals A'-1 , A'-1 a, A'-1 b, A'-2, A'-2a, A'-2b, A'-3, A'-3a and A'-3b:
  • T is preferably selected from the group consisting of CHR xa , CH(R xa )CH(R xa ) and cyclopropane-1 ,2-diyl.
  • R xa independently of each other, preferably are selected from the group consisting of H and Ci-C4-allkyl, in particular from the group consisting of H and CH3.
  • R xa is more particularly H.
  • T is in particular selected from the group consisting of a single bond, CH2, CH2CH2 and 1 ,2-cycloprandiyl.
  • X 1 is is preferably selected from the group consisting of
  • R x2 is preferably selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-CrC4-alkyl, C3-C6-cycloalkyl, C3-C6-cyclo- alkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R x2 is in particular H or Ci-C4-alkyl, more particularly H.
  • R x3 is preferably selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cyclo- alkyl-Ci-C4-alkyl, where the alkyl, cycloalkyi and alkoxy parts of the last 3 mentioned radicals are unsubstituted or partially or completely halogenated, and phenyl, where the phenyl ring is unsubstituted or carries 1 , 2 or 3 radicals R f .
  • R x3 is in particular H or Ci-C4-alkyl, more particularly H.
  • R ⁇ 1 , R ⁇ 2 are preferably selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C4- alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R ⁇ 1 , R ⁇ 2 are in particular H or Ci-C4-alkyl, more particularly H.
  • R ⁇ 3 is preferably selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-CrC4-alkyl, C3-C6-cycloalkyl, C3-C6-cyclo- alkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-CrC4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R ⁇ 3 is in particular H or Ci-C4-alkyl, more particularly H.
  • Z 1 is preferably selected from the group consisting of O and -N-R z1 .
  • R z1 is preferably selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-CrC4-alkyl, C3-C6-cycloalkyl, C3-C6-cyclo- alkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-CrC4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halo- genated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R z1 is in particular H or Ci-C4-alkyl, more particularly H.
  • R' is preferably selected from H, CN and Ci-C 4 -alkyl.
  • R z3 , R z4 and R z5 are as defined above and have in particular the following meanings:
  • R z3 is selected from the group consisting of H, halogen, such as F or CI, CN, Ci-C6-alkyl and Ci-C6-haloalkyl, more preferably from the group consisting of H, F, CI, CN andCH3and more particularly H or CN;
  • R z4 is selected from the group consisting of H, Ci-C6-alkyl and Ci-C6-haloalkyl, more preferably from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl, more particularly CH3, C2H5 or trifluoromethyl;
  • R z5 is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R z5 is in particular H or Ci-C4-alkyl, more particularly H.
  • R' is preferably selected from H, CN and Ci-C4-alkyl.
  • R y4 is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R y4 is in particular H or Ci-C4-alkyl, more particularly H.
  • R y44 is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl and benzyl, where the phenyl ring in benzyl is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R ⁇ 44 is in particular H or Ci-C4-alkyl, more particularly H.
  • R z6 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3- C6-cycloalkyl-Ci-C4-alkyl, where the alkyl, cycloalkyl parts of the last two mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R z6 is in particular Ci-C4-alkyl or Ci-C4-haloalkyl, more particularly CH3, C2H5 or trifluoromethyl.
  • R' is preferably selected from H, CN and Ci-C4-alkyl.
  • R x1 , R x2 independently of each other, are selected from the group consisting of H, Ci-C6-al- kyl, Ci-Ce-haloalkyI, Ci-C 6 -alkoxy-Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C 4 -al- kyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyl, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated,
  • R x3 is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, where the alkyl, cycloalkyl and alkoxy parts of the last 3 mentioned radicals are unsubstituted or partially or completely halogenated,
  • Ry "1 , Ry 2 independently of each other, are selected from the group consisting of H, Ci-C6-al- kyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-al- kyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halo- genated,
  • Ry 3 is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated,
  • R z1 is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C4-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated,
  • R z3 is selected from the group consisting of H, halogen, such as F or CI, CN, Ci-C6-alkyl and Ci-C6-haloalkyl, more preferably from the group consisting of H, F, CI, CN andCh and more particularly H or CN;
  • R z4 is selected from the group consisting of H, Ci-C6-alkyl and Ci-C6-haloalkyl, more preferably from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl, more particularly CH3, C2H5 or trifluoromethyl;
  • R z5 is selected from the group consisting of H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C4-alkyl, C 3 -C6-cycloalkyl, C 3 -C6-cycloalkyl-Ci-C4-alkyl, C 3 -C6-cycloalkoxy-Ci-C4-alkyl, where the alkyl, cycloalkyi, cycloalkoxy and alkoxy parts of the last four mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R z5 is in particular H or Ci-C4-alkyl, more particularly H;
  • R z6 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3- C6-cycloalkyl-Ci-C4-alkyl, where the alkyl, cycloalkyi parts of the last two mentioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where the phenyl ring in the last 2 radicals is unsubstituted or carry 1 , 2 or 3 radicals R f .
  • R z6 is in particular Ci-C4-alkyl or Ci-C4-haloalkyl, more particularly CH3, C2H5 or trifluoromethyl;
  • Ry 4 together with R z6 may also form a linear Ci-C4-alkylene group, such as CH2, CH2CH2 or
  • R z1 together with R y3 may also form a linear Ci-C4-alkylene group, such as Ch , CH2CH2 or
  • R z4 together with R z5 may also form a linear Ci-C 4 -alkylene group, such as CH2, CH2CH2 or
  • R hh is selected from the group consisting of OH, halogen, such asCI orF, CrC 4 -alkyl such as CH3, C2H5, n-propyl or isopropyl, and fluorinated Ci-C 4 -alkyl such as trifluoromethyl;
  • R' is selected from H, CN and Ci-C 4 -alkyl.
  • R x1 , R x2 independently of each other, are selected from the group consisting of H and C1-C4- alkyl such as CH3, C2H5, n-propyl or isopropyl;
  • R x3 is selected from the group consisting of H and Ci-C 4 -alkyl such as CH3, C2H5, n-propyl or isopropyl;
  • R y1 , R y2 independently of each other, are selected from the group consisting of H and C1-C4- alkyl such as CH 3 , C2H5, n-propyl or isopropyl;
  • R y3 is selected from the group consisting of H and Ci-C 4 -alkyl such as CH3, C2H5, n-propyl or isopropyl;
  • R y4 is selected from the group consisting of H and Ci-C 4 -alkyl such as CH3, C2H5, n-propyl or isopropyl;
  • R y44 is selected from the group consisting of H and Ci-C 4 -alkyl such as CH3, C2H5, n-propyl or isopropyl;
  • R z1 is selected from the group consisting of H and CrC 4 -alkyl such as CH 3 , C2H5, n-propyl or isopropyl; or
  • R h is selected from the group consisting of H, CH 3 , CN and trifluoromethyl
  • R hh is selected from the group consisting of CH 3 , CN and trifluoromethyl
  • R' is selected from the group consisting of H, CH 3 and CN.
  • radical R 1 is preferably selected from the moieties of the formulae R 1 -1 to R 1 -60:
  • R ⁇ R 11 , R X2 , R x3 , Rv Rv 2 , Rv 3 , Rv 4 , R z1 , R z3 , R z4 , R z5 and R z6 are as defined in claim 1
  • a 0 is C(R h )2 or C(R h )2C(R h )2 and R h , irrespectively of its occurrence, is selected from H or has one of the meanings given for R hh , and where R h is in particular selected from the group consisting of H, CH3, CN and trifluoromethyl.
  • the radical R 11 is preferably C3-C6-cycloalkyl, aryl, aryl- Ci-C4-alkyl, hetaryl, or hetaryl-Ci-C4-alkyl, where the aryl and hetaryl rings in the last 4 radicals are unsubstituted or carry 1 , 2, 3, 4 or 5 radicals Rs and where hetaryl in hetaryl or hetaryl-Ci- C4-alkyl, is preferably a 5- or 6-membered monocyclic hetaryl such as pyridyl, pyrimidinyl, pyri- dazinyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl or isothiazolyl which 5- or 6- membered hetaryl is unsubstituted or carries 1 , 2 or 3 radicals Rs.
  • the radical R 11 is more preferably phenyl, benzyl, 1-phe- nylethyl, pyridyl, pyridyl- CH3 and 1 -(pyridyl)ethyl, where phenyl and pyridyl in the last 6 radicals may be unsubstituted or preferably carry 1 , 2 or 3 radicals Rs.
  • the radicals Rs are independently of each other selected from the group consisting of halogen, such asF,CI orBr, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, Ci-C6-haloalkyl, in particular fluorinated Ci-C3-alkyl such as CH2F, CHF2, CF 3 , CH2CF3, CF2CHF2, C 2 F 5 , CH2CH2CF3, CH2CF2CHF2, or CH 2 CF 2 CF 3 , C C 6 -alkoxy, in par- ticular Ci-C3-alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloalkoxy, in particular fluorinated Ci-C 3 -alkoxy such as OCH 2 F, OCHF 2 , OCF 3 , OCH2CF3, OCF
  • radicals R 11 are the radicals R 11 -1 to R 11 -29 summarized in Table B below.
  • variables R x1 , R a , R b , R c , R d , R e , R f and Rs independently of each other, preferably have one of the following meanings:
  • each R a is independently selected from the group consisting of Ci-C6-alkyl, Ci- C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, benzyl and phenyl, where the phenyl ring in the last two radicals is unsubstituted or may be substituted by 1 , 2 or 3 radicals R f .
  • R c and R d are, independently of each other and independently of their occurrence, selected from the group consisting of H, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl- CH 2 , C3-C6-cycloalkyl, benzyl and phenyl, where the phenyl ring in the last two radicals is unsubstituted or may be substituted by 1 , 2 or 3 radicals R f ; or
  • R b and R c together with the nitrogen atom to which they are bound may form a saturated 5-, 6- or 7-membered saturated N-bound heterocycle, which may contain 1 or 2 further heteroa- toms selected from N, O and S as ring members, where the heterocyclic ring may carry 1 , 2, 3 or 4 substituents selected from Ci-C4-alkyl, examples including 1 -pyrrolidinyl, 1-piperidinyl, 1- piperazinyl, 4-methyl-1 -piperazinyl, 4-morpholinyl and 4-thiomorpholinyl.
  • each R d is independently selected from the group consisting of Ci-C4-alkyl, Ci- C4-haloalkyl, Cs-Cs-cycloalkyl, benzyl and phenyl, where the phenyl ring in the last two radicals is unsubstituted or may be substituted by 1 , 2 or 3 radicals R f .
  • each R e is independently selected from the group consisting of Ci-C4-alkyl, Ci- C4-haloalkyl, Cs-Cs-cycloalkyl, benzyl and phenyl, where the phenyl ring in the last two radicals is unsubstituted or may be substituted by 1 , 2 or 3 radicals R f .
  • each R f is independently selected from the group consisting of halogen, in par- ticularF,CI orBr, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxycarbonyl, cyano, Ci-C4-alkoxy and Ci-C4-haloalkoxy, more particularly from the group consisting of halogen, in particularF,CI orBr, CH3, halomethyl, e.g. trifluoromethyl, difluoromethyl or bromodifluoromethyl, cyano, methoxy and halomethoxy, e.g. trifluoromethoxy, difluoromethoxy or fluoromethoxy. If two or more radicals R f are present, it is possible that the radicals R f are identical or different.
  • R9 are independently of each other selected from the group consisting of halogen, such asF,CI orBr, Ci-C6-alkyl, in particular Ci-C3-alkyl such as CH3, C2H5, n-propyl or isopropyl, Ci- Ce-haloalkyl, in particular fluorinated Ci-C 3 -alkyl such as CH 2 F, CHF 2 , CF 3 , CH2CF3, CF2CHF2, C2F5, CH2CH2CF3, CH2CF2CHF2, or CH2CF2CF3, Ci-C 6 -alkoxy, in particular Ci-C 3 -alkoxy such as methoxy, ethoxy, n-propyloxy or isopropyloxy, Ci-C6-haloalkoxy, in particular fluorinated Ci- Cs-alkoxy such as OCH 2 F, OCHF 2 , OCF 3 , OCH2CF3, OCF 2 CHF 2 , OC2F5, OCH 2 CH
  • Table 1 Compounds of the formula 1-1 , their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 2 Compounds of the formula I-2, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 3 Compounds of the formula I-3, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 4 Compounds of the formula I-4, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 5 Compounds of the formula I-5, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 6 Compounds of the formula I-6, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 7 Compounds of the formula 1-6, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 8 Compounds of the formula I-7, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 9 Compounds of the formula I-8, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 10 Compounds of the formula I-9, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 1 Compounds of the formula 1-10, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 12 Compounds of the formula 1-1 1 , their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 13 Compounds of the formula 1-12, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 14 Compounds of the formula 1-12, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 15 Compounds of the formula 1-13, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 16 Compounds of the formula 1-14, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 17 Compounds of the formula 1-15, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 18 Compounds of the formula 1-16, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 19 Compounds of the formula 1-17, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 20 Compounds of the formula 1-18, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 21 Compounds of the formula 1-18, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 22 Compounds of the formula 1-19, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 23 Compounds of the formula I-20, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 24 Compounds of the formula 1-21 , their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 25 Compounds of the formula I-22, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 26 Compounds of the formula I-23, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 27 Compounds of the formula I-24, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 28 Compounds of the formula I-24, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 29 Compounds of the formula I-25, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 30 Compounds of the formula I-26, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 31 Compounds of the formula I-27, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 32 Compounds of the formula I-28, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 33 Compounds of the formula I-29, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 34 Compounds of the formula I-30, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 35 Compounds of the formula 1-30, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 36 Compounds of the formula 1-31 , their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 37 Compounds of the formula I-32, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 38 Compounds of the formula I-33, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 39 Compounds of the formula I-34, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 40 Compounds of the formula I-35, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 41 Compounds of the formula I-36, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 42 Compounds of the formula I-36, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 43 Compounds of the formula I-37, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 44 Compounds of the formula I-38, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 45 Compounds of the formula I-39, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 46 Compounds of the formula I-40, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 47 Compounds of the formula 1-41 , their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 48 Compounds of the formula I-42, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 49 Compounds of the formula 1-42, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 50 Compounds of the formula I-43, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 51 Compounds of the formula I-44, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 52 Compounds of the formula I-45, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 53 Compounds of the formula I-46, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 54 Compounds of the formula I-47, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 55 Compounds of the formula I-48, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 56 Compounds of the formula I-48, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 57 Compounds of the formula I-49, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 58 Compounds of the formula I-50, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 59 Compounds of the formula 1-51 , their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 60 Compounds of the formula I-52, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 61 Compounds of the formula I-53, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 62 Compounds of the formula I-54, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 63 Compounds of the formula 1-54, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 64 Compounds of the formula I-55, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 65 Compounds of the formula I-56, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 66 Compounds of the formula I-57, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 67 Compounds of the formula I-58, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 68 Compounds of the formula I-59, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 69 Compounds of the formula I-60, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 70 Compounds of the formula I-60, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 71 Compounds of the formula 1-61 , their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 72 Compounds of the formula I-62, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 73 Compounds of the formula I-63, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 74 Compounds of the formula I-64, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 75 Compounds of the formula I-65, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 76 Compounds of the formula I-66, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 77 Compounds of the formula 1-66, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 78 Compounds of the formula I-67, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 79 Compounds of the formula I-68, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 80 Compounds of the formula I-69, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 81 Compounds of the formula I-70, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 82 Compounds of the formula 1-71 , their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 83 Compounds of the formula I-72, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 84 Compounds of the formula I-72, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 85 Compounds of the formula I-73, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 86 Compounds of the formula I-74, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 87 Compounds of the formula I-75, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 88 Compounds of the formula I-76, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 89 Compounds of the formula I-77, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 90 Compounds of the formula I-78, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 91 Compounds of the formula I-78, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 92 Compounds of the formula I-79, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 93 Compounds of the formula I-80, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 94 Compounds of the formula 1-81 , their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 95 Compounds of the formula I-82, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 96 Compounds of the formula I-83, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 97 Compounds of the formula I-84, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 98 Compounds of the formula I-84, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 99 Compounds of the formula I-85, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 100 Compounds of the formula I-86, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 101 Compounds of the formula I-87, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 102 Compounds of the formula I-88, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 103 Compounds of the formula I-89, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 104 Compounds of the formula I-90, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 105 Compounds of the formula I-90, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 106 Compounds of the formula 1-91 , their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R 1 is a radical -XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 107 Compounds of the formula I-92, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 108 Compounds of the formula I-93, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 109 Compounds of the formula I-94, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respec- tively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 10 Compounds of the formula I-95, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 1 1 Compounds of the formula I-96, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 12 Compounds of the formula I-96, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 13 Compounds of the formula I-97, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 14 Compounds of the formula I-97, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH 3 , R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 15 Compounds of the formula I-98, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 16 Compounds of the formula I-98, their stereoisomers, their tautomers and the agricul- turally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 17 Compounds of the formula I-99, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ-R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 18 Compounds of the formula I-99, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 1 19 Compounds of the formula 1-100, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 120 Compounds of the formula 1-100, their stereoisomers, their tautomers and the agri- culturally or veterinarily acceptable salts, wherein R Q2 is CH 3 , R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 121 Compounds of the formula 1-101 , their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 122 Compounds of the formula 1-101 , their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 123 Compounds of the formula 1-102, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 124 Compounds of the formula 1-102, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 125 Compounds of the formula 1-103, their stereoisomers, their tautomers and the agri- culturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 126 Compounds of the formula 1-103, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 127 Compounds of the formula 1-104, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 128 Compounds of the formula 1-104, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH 3 , R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 129 Compounds of the formula 1-105, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 130 Compounds of the formula 1-105, their stereoisomers, their tautomers and the agri- culturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 131 Compounds of the formula 1-106, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 132 Compounds of the formula 1-106, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 133 Compounds of the formula 1-107, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 134 Compounds of the formula 1-107, their stereoisomers, their tautomers and the agri- culturally or veterinarily acceptable salts, wherein R Q2 is CH 3 , R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 135 Compounds of the formula 1-108, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 136 Compounds of the formula 1-108, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 137 Compounds of the formula 1-109, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 138 Compounds of the formula 1-109, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 139 Compounds of the formula 1-1 10, their stereoisomers, their tautomers and the agri- culturally or veterinarily acceptable salts, wherein R Q2 is H, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Table 140 Compounds of the formula 1-1 10, their stereoisomers, their tautomers and the agriculturally or veterinarily acceptable salts, wherein R Q2 is CH3, R 1 is a radical XYZ-R 11 or XYZ- R 12 , respectively, where Ar, -XYZ- and R 11 /R 12 are as defined in the rows of table C.
  • Tables 141 to 280 Compounds of the formulae 1-1 to 1-1 10, which correspond to the compounds of the formulae -1 to 1-1 10 summarized in tables 1 to 140, wherein Ar is Ar-2 instead of Ar-1 .
  • Tables 281 to 420 Compounds of the formulae 1-1 to 1-1 10, which correspond to the compounds of the formulae -1 to 1-1 10 summarized in tables 1 to 140, wherein Ar is Ar-3 instead of Ar-1 .
  • Tables 421 to 560 Compounds of the formulae 1-1 to 1-1 10, which correspond to the compounds of the formulae -1 to 1-1 10 summarized in tables 1 to 140, wherein Ar is Ar-4 instead of Ar-1 .
  • Tables 461 to 700 Compounds of the formulae 1-1 to 1-1 10, which correspond to the compounds of the formulae -1 to 1-1 10 summarized in tables 1 to 140, wherein Ar is Ar-5 instead of Ar-1 .
  • Tables 701 to 840 Compounds of the formulae 1-1 to 1-1 10, which correspond to the compounds of the formulae -1 to 1-1 10 summarized in tables 1 to 140, wherein Ar is Ar-6 instead of Ar-1 .
  • Tables 841 to 980 Compounds of the formulae 1-1 to 1-1 10, which correspond to the compounds of the formulae -1 to 1-1 10 summarized in tables 1 to 140, wherein Ar is Ar-7 instead of Ar-1 .
  • Tables 981 to 1 120 Compounds of the formulae 1-1 to 1-1 10, which correspond to the compounds of the formulae 1-1 to 1-1 10 summarized in tables 1 to 140, wherein Ar is Ar-8 instead of Ar-1 .
  • Tables 1 121 to 1260 Compounds of the formulae 1-1 to 1-1 10, which correspond to the com- pounds of the formulae 1-1 to 1-1 10 summarized in tables 1 to 140, wherein Ar is Ar-9 instead of Ar-1 .
  • Ar-1 XYZ-8 R 1 1-12 213.
  • Ar-1 XYZ-9 R 1 1-21 Ar -X-Y-Z- R11/R12 Ar -X-Y-Z- R11/R12
  • Ar-1 XYZ-1 1 R11.1 289.
  • Ar-1 XYZ-12 R 11 -10 Ar -X-Y-Z- R11/R12 Ar -X-Y-Z- R11/R12
  • Ar-1 XYZ-17 R 11 -17 Ar -X-Y-Z- R11/R12 Ar -X-Y-Z- R11/R12
  • Ar-1 XYZ-20 R -6 Ar -X-Y-Z- R11/R12 Ar -X-Y-Z- R11/R12
  • Ar-1 XYZ-29 R 11 -11 821.
  • Ar-1 XYZ-30 R11.20 Ar -X-Y-Z- R11/R12 Ar -X-Y-Z- R11/R12
  • Ar-1 XYZ-31 R11.29 897.
  • Ar-1 XYZ-33 R -9 Ar -X-Y-Z- R11/R12 Ar -X-Y-Z- R11/R12

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Abstract

La présente invention concerne de nouveaux composés imidazoisoquinoléine de formule I et les N-oxydes, les stéréoisomères, les tautomères et les sels pharmaceutiquement acceptables du point de vue agricole ou vétérinaire de ces derniers, dans laquelle A1 est N ou C(R2), A2 est N ou C(R3) ; A3 est N ou C(R4) ; A4 est N ou C(R5) ; A5 est N ou C(R6) ; et où Ar, R, R1, R2, R3, R4,R5 et R6 sont tels que définis dans les revendications. Les composés de formule (I), ainsi que les N-oxydes, les stéréoisomères, les tautomères et les sels pharmaceutiquement acceptables du point de vue agricole ou vétérinaire de ces derniers, sont utiles pour combattre ou lutter contre des organismes nuisibles invertébrés, en particulier les organismes nuisibles arthropodes et les nématodes. La présente invention concerne également un procédé de lutte contre des organismes nuisibles invertébrés à l'aide de ces composés, un matériel de propagation des végétaux et une composition agricole et une composition vétérinaire comprenant lesdits composés.
PCT/EP2016/050496 2015-01-14 2016-01-13 Composés imidazoisoquinoléine, compositions comprenant les composés et leur utilisation pour lutter contre des organismes nuisibles invertébrés WO2016113271A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10440953B2 (en) 2015-08-07 2019-10-15 Basf Se Control of pests in maize by ginkgolides and bilobalide
US10526264B2 (en) 2016-07-07 2020-01-07 Basf Se Oxy-cope rearrangement for the manufacture of insecticidal cyclopentene compounds
WO2022132609A1 (fr) * 2020-12-14 2022-06-23 Corteva Agriscience Llc Molécules présentant certaines utilités pesticides, et intermédiaires, compositions et procédés associés

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WO2009148916A1 (fr) * 2008-06-03 2009-12-10 Merck & Co., Inc. Inhibiteurs de l'activité akt
WO2011017504A1 (fr) * 2009-08-07 2011-02-10 Dow Agrosciences Llc Compositions pesticides
EP2738171A1 (fr) * 2012-11-30 2014-06-04 Syngenta Participations AG. Dérivés tricycliques de pyridyle avec un principe pesticide actif
WO2015007682A1 (fr) * 2013-07-15 2015-01-22 Basf Se Composés pesticides

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WO2009148916A1 (fr) * 2008-06-03 2009-12-10 Merck & Co., Inc. Inhibiteurs de l'activité akt
WO2011017504A1 (fr) * 2009-08-07 2011-02-10 Dow Agrosciences Llc Compositions pesticides
EP2738171A1 (fr) * 2012-11-30 2014-06-04 Syngenta Participations AG. Dérivés tricycliques de pyridyle avec un principe pesticide actif
WO2015007682A1 (fr) * 2013-07-15 2015-01-22 Basf Se Composés pesticides

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Title
FARNAZ JAFARPOUR ET AL: "A Novel One-Step Synthesis of Imidazo[5,1- a ]isoquinolines via a Tandem Pd-Catalyzed Alkylation-Direct Arylation Sequence", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 74, no. 3, 6 February 2009 (2009-02-06), US, pages 1364 - 1366, XP055260261, ISSN: 0022-3263, DOI: 10.1021/jo802584f *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10440953B2 (en) 2015-08-07 2019-10-15 Basf Se Control of pests in maize by ginkgolides and bilobalide
US10526264B2 (en) 2016-07-07 2020-01-07 Basf Se Oxy-cope rearrangement for the manufacture of insecticidal cyclopentene compounds
WO2022132609A1 (fr) * 2020-12-14 2022-06-23 Corteva Agriscience Llc Molécules présentant certaines utilités pesticides, et intermédiaires, compositions et procédés associés

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