WO2015107117A1 - Composés (het)arylalcényle et leur utilisation pour lutter contre les nuisibles invertébrés - Google Patents

Composés (het)arylalcényle et leur utilisation pour lutter contre les nuisibles invertébrés Download PDF

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Publication number
WO2015107117A1
WO2015107117A1 PCT/EP2015/050693 EP2015050693W WO2015107117A1 WO 2015107117 A1 WO2015107117 A1 WO 2015107117A1 EP 2015050693 W EP2015050693 W EP 2015050693W WO 2015107117 A1 WO2015107117 A1 WO 2015107117A1
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alkyl
hydrogen
group
cycloalkyl
radicals
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PCT/EP2015/050693
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English (en)
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Wolfgang Von Deyn
Pascal BINDSCHÄDLER
Franz Josef Braun
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • (Het)Arylalkenyl compounds and their use for controlling invertebrate pests Description
  • the present invention relates to (het)arylalkenyl 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.
  • the invention relates to (het)arylalkenyl compounds of formula I
  • B 1 , B 2 , B 3 , B 4 and B 5 are each independently selected from the group consisting of N and C-R 2 , with the proviso that at most two of B 1 , B 2 , B 3 , B 4 and B 5 are N;
  • G 1 is selected from the group consisting of N and C-R 4b ;
  • G 2 , G 3 and G 5 are each independently selected from the group consisting of N and C- R 4 ;
  • G 4 is selected from the group consisting of N, C-A and C-R 4 ; with the proviso that at most two of G 2 , G 3 , G 4 and G 5 are N;
  • A is a group A 1 , A 2 , A 3 or A 4 ,
  • a 2 is a group of following formula:
  • # denotes the bond to the remainder of the molecule; W is selected from O and S;
  • Y is selected from hydrogen, -N(R 5 )R 6 and -OR 9 ;
  • a 3 is a group of following formula: (A 3 )
  • a 4 is a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, or is a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2, 3 or 4 heteroa- toms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring is optionally substituted with one or more substituents R 11 ; is selected from O and S; is selected from the group consisting of Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, Ci-C4-alkylsul
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 11 , and a 3-, 4-, 5-, 6-
  • R 4 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2- C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 ,
  • phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted by one or more radicals R 11 ;
  • -S(0) n R 9 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , d-Ce-alkyl, Cs-Cs-cycloalkyl, C2-Ce-alkenyl, C2-C6- alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 ,
  • each R 5 is independently selected from the group consisting of hydrogen, C1-C10- alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last- mentioned aliphatic and cycloali
  • R 7a , R 7b are each independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be par- tially or fully halogenated and/or may be substituted by one or more radicals R 8 ; each R 8 is independently selected from the group consisting of cyano, azido, nitro, - SCN, -SF 5 , Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more radicals R 13 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally un- saturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R 16 , or
  • R 8 together with the carbon atoms of an alkyl, alkenyl, alkynyl or cycloalkyi group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2 as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R 16 ; and
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 R 16 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the het- erocyclic ring is optionally substituted with one or more substituents R 16 ;
  • R 9 in the groups -S(0) n R 9 and -OSO2R 9 is additionally selected from the group consisting of Ci-C6-alkoxy and Ci-C6-haloalkoxy;
  • R 10a , R 10b are selected independently from one another from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 3 -C8-cycloalkyl, C 3 -C8-halocycloalkyl, C2-
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R 16 ;
  • R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more sub- stituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-
  • each R 11 is independently selected from the group consisting of halogen, cyano, az- ido, nitro, -SCN, -SF 5 , Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-C10- alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more radicals R 8 ,
  • phenyl optionally substituted with 1 , 2, 3, 4, or 5 substituents selected independently from R 16 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more substituents selected independently from R 16 ;
  • R 11 bound on adjacent ring atoms form together with the ring atoms to which they are bound a saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, where- in the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from
  • Cs-Cs-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkyl, C3-C4-cycloalkyl, Ci- C4-alkoxy, Ci-C4-haloalkoxy and oxo; phenyl, benzyl, pyridyl, phenoxy, where the cyclic moiety in the four last-mentioned radicals may be unsubstituted or carry 1 , 2, 3, 4 or 5 substituents R 16 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring may be substituted by 1 , 2 or 3 substituents R 16 ;
  • R 13 as a substituent on a cycloalkyl ring is additionally selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last- mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 substituents selected from CN , C3-C4-cycloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy and oxo;
  • R 14 is independently selected from the group consisting of hydrogen, cyano, Ci- C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl,
  • cyclic moieties in the four last- mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3 substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 or 2 het- eroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R 16 : and R 14b , independently of each other, have one of the meanings given for R 14 ; or
  • R 14a and R 14b together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy;
  • R 15 is independently selected from the group consisting of hydrogen, cyano, trimethylsilyl, triethylsilyl, ferf-butyldimethylsilyl,
  • Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkyl, C3-C4-cycloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl and oxo;
  • phenyl, benzyl, pyridyl and phenoxy wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl;
  • R 16 is independently selected from the group consisting of halogen, nitro, cyano, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl;
  • phenyl, benzyl, pyridyl and phenoxy wherein the four last-mentioned radicals may be partially or fully halogenated and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (C1-C6- alkoxy)carbonyl;
  • two R 16 on two adjacent carbon atoms form together with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 as ring members, and wherein the ring optionally carries one or more substituents selected from halogen, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy; each n is independently 0, 1 or 2; and
  • each m is independently 0 or 1 ; and the N-oxides, tautomers, stereoisomers and agriculturally or veterinarily acceptable salts thereof.
  • the present invention also provides an agricultural composition
  • an agricultural composition comprising at least one compound of the formula I as defined herein, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof and at least one inert liquid and/or solid agriculturally acceptable carrier.
  • the present invention also provides a veterinary composition
  • a veterinary composition comprising at least one compound of the formula I as defined herein, a stereoisomer thereof and/or a veterinar- ily acceptable salt thereof and at least one inert liquid and/or solid verterinarily acceptable carrier.
  • the present invention also provides a method for 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 pesticidally effective amount of a compound of formula I or a salt thereof as defined herein, a stereoisomer thereof and/or at least one salt thereof as defined herein.
  • the method does not comprise the treatment of the human or animal body.
  • the method serves for protecting plants from attack or infestation by invertebrate pests, and comprises treating the plants with a pesticidally effective amount of at least one compound of the formula I as defined herein, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.
  • the method especially further serves for protecting plant propagation material and/or the plants which grow therefrom from attack or infestation by invertebrate pests, and comprises treating the plant propagation material with a pesticidally effective amount of at least one compound of the formula I as defined herein, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.
  • the present invention also relates to plant propagation material, in particular seed, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof as defined herein.
  • the present invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of at least one compound of the formula I, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof as defined herein.
  • Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal.
  • stereoisomers encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • These possible cis/trans stereoisomers are represented by the zigzag lines in formula I and by the "intersected" (X-shaped) double bond. In some of the below formulae the possible cis/trans isomers are represented only by zigzag lines.
  • 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 diastereomers.
  • 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 stereoisomers (cis/trans isomers) and mixtures thereof.
  • the term N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO).
  • N-oxides of compounds I can in particular be prepared by oxidizing e.g.
  • the ring nitrogen atom of the ring containing as ring member B 1 to B 5 or G 1 to G 5 (if any of these ring members are N), and/or of any nitrogen-containing heterocyclic group present in group A 1 to A 4 , R 2 , R 4 , R 4b , R 5 , R 6 , R 8 , R 9 , R 0a , R 0b , R 11 , R 13 , R 4 , R 4a , R 4b , R 15 , or R 16 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 ore 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 acceptable 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 especially 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 hydrogen atoms are replaced by Ci-C 4 -alkyl, Ci-C 4 -hydroxyalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy- Ci-C 4 -alkyl, hydroxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammo- nium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethyl- ammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)- ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl- triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C 4 -alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C 4 -alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyr- ate. They can be formed by reacting a compound of formulae 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 hydrochloride, 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 hydrochloride, sulphates, phosphates, and nitrates
  • 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 insects, 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 related genera of a cultivated plant.
  • cultivated plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://www.bio.org).
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under 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, acety- lated 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.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially 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. or
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins
  • agglutinins protein- ase 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 or calcium channels
  • these 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 und 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.
  • 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, especially to beetles (Coeloptera), 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 toler- ance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called “ pathogenesis-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 infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of syn- thesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • T4-lysozym e. g. potato cultivars capable of syn- thesizing these proteins with increased resistance against bacteria such as Erwinia amylvora.
  • 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.
  • 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
  • plants are also covered that contain by the use of recombinant DNA techniques 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 techniques 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).
  • 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 -C m indicates in each case the possible number of carbon atoms in the group.
  • halogen denotes in each case fluorine, bromine, chlorine or iodine, in particu- lar fluorine, chlorine or bromine.
  • alkyl as used herein and in the alkyl moieties of alkoxy, alkylthio, alkylsulfi- nyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl and the like refers to saturated straight- chain or branched hydrocarbon radicals having 1 to 2 ("Ci-C2-alkyl"), 1 to 3 (“C1-C3- alkyl"), 1 to 4 (“Ci-C 4 -alkyl”), 1 to 6 (“Ci-C 6 -alkyl”), 1 to 8 (“Ci-C 8 -alkyl”) or 1 to 10 (“Ci- Cio-alkyl”) carbon atoms.
  • Ci-C2-Alkyl is methyl or ethyl.
  • 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-dimethylpropyl, 1 - ethylpropyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3- dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2- ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl, or 1 - eth
  • Ci-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2- ethylhexyl and positional isomers thereof.
  • Ci-Cio-Alkyl is additionally also, for example, nonyl, decyl and positional isomers thereof.
  • haloalkyl as used herein, which is also expressed as “alkyl which is partially or fully halogenated”, refers to straight-chain or branched alkyl groups having 1 to 2 (“Ci-C 2 -haloalkyl”), 1 to 3 (“Ci-C 3 -haloalkyl”), 1 to 4 (“Ci-C 4 -haloalkyl”), 1 to 6 (“Ci-C 6 - haloalkyl”), 1 to 8 (“Ci-C 8 -haloalkyl”) or 1 to 10 (“Ci-Cio-haloalkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluorome- thyl, trifluoromethyl, chlorofluoromethyl,
  • 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, heptafluoro- propyl, 1 ,1 ,1 -trifluoroprop-2-yl, 3-chloropropyl and the like.
  • Examples for Ci-C 4 - haloalkyl are, apart those mentioned for Ci-C3-haloalkyl, 4-chlorobutyl and the like.
  • alkenyl refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C2-C3-alkenyl"), 2 to 4 (“C 2 -C4-alkenyl”), 2 to 6 (“C 2 -C 6 -alkenyl”), 2 to 8 (“C 2 -C 8 -alkenyl”) or 2 to 10 (“C 2 -Cio-alkenyl”) carbon atoms and a double bond in any position, for example C 2 -C3-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl or 1 -methylethenyl; C 2 -C4-alkenyl, such as ethenyl, 1 -propenyl,
  • 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"), 2 to 6 (“C 2 -C 6 -haloalkenyl”), 2 to 8 (“C 2 -C 6 -haloalkenyl”) or 2 to 10 (“C 2 -Cio-haloalkenyl”) carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, 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”), 2 to 6 (“C 2 -C 6 -alkynyl”), 2 to 8 (“C2-C8-alkynyl”), or 2 to 10 (“C2-Cio-alkynyl”) carbon atoms and one or two triple bonds in any position, for example C2-C3-alkynyl, such as ethynyl, 1 -propynyl or 2- propynyl; C2-C 4 -alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl and the like, C2-C6-alkyny
  • 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”), 2 to 6 (“C 2 -C 6 -haloalkynyl”), 2 to 8 (“C 2 -C 8 -haloalkynyl”) or 2 to 10 (“C2-Cio-haloalkynyl”) carbon atoms and one or two triple bonds in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine;
  • cycloalkyl refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having 3 to 8 (“Cs-Cs-cycloalkyl"), in particular 3 to 6 (“C3-C6- cycloalkyl") or 3 to 5 (“C 3 -C 5 -cycloalkyl”) or 3 to 4 (“C 3 -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, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Examples of bicyclic radicals hav- ing 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicy- clo[2.2.2]octyl and bicyclo[3.2.1 ]octyl.
  • cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
  • halocycloalkyl as used herein, which is also expressed as “cycloalkyi which is partially or fully halogenated”, refers to mono- or bi- or polycyclic saturated hydrocarbon groups having 3 to 8 (“Cs-Cs-halocycloalkyl” ) or preferably 3 to 6 (“C3-C6- halocycloalkyl") or 3 to 5 (“C 3 -C 5 -halocycloalkyl”) or 3 to 4 (“C 3 -C 4 -halocycloalkyl”) car- bon ring members (as mentioned above) in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • halocyclopropyl as used herein, which is also expressed as “cyclopropyl which is partially or fully halogenated”, refers to cyclopropyl in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • Examples are 1 -fluorocyclopropyl, 2-fluorocyclopropyl, 1 ,2- difluorocyclopropyl, 2,2-difluorocyclopropyl, 2,3-difluorocyclopropyl, 1 ,2,2- trifluorocyclopropyl, 1 ,2,3-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1 - chlorocyclopropyl, 2-chlorocyclopropyl, 1 ,2-dichlorocyclopropyl, 2,2- dichlorocyclopropyl, 2,3-dichlorocyclopropyl, and the like.
  • cycloalkyl-Ci-C 4 -alkyl refers to a Cs-Cs-cycloalkyl group ("Cs-Cs-cycloalkyl- Ci-C 4 -alkyl”), preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-Ci-C 4 -alkyl”), more preferably a C3-C 4 -cycloalkyl group (“C3-C 4 -cycloalkyl-Ci-C 4 -alkyl”) as defined above (preferably a monocyclic cycloalkyi group) which is bound to the remainder of the molecule via a Ci-C 4 -alkyl group, as defined above.
  • Examples for C3-C 4 -cycloalkyl-Ci-C 4 - alkyl are cyclopropyl methyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cy- clobutylethyl and cyclobutylpropyl,
  • Examples for C3-C6-cycloalkyl-Ci-C 4 -alkyl, apart those mentioned for C3-C 4 -cycloalkyl-Ci-C 4 -alkyl, are cyclopentylmethyl, cyclopen- tylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
  • C 3 -C 8 -halocycloalkyl-Ci-C 4 -alkyl and "C 3 -C 6 -halocycloalkyl-Ci-C 4 -alkyl” refers to a Cs-Cs-halocycloalkyl or C3-C6-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C 4 -alkyl group, as defined above.
  • Ci-C2-alkoxy is a Ci-C2-alkyl group, as defined above, attached via an oxy- gen atom.
  • Ci-C3-alkoxy is a Ci-C3-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 4 -alkoxy is a Ci-C 4 -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-propoxy and 1 -methylethoxy (iso- propoxy).
  • Ci-C 4 -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-methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethyl propoxy, hexoxy, 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-dimethylbutoxy, 1 -ethylbutoxy, 2-ethyl butoxy, 1 ,1 ,2- trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1-methylpropoxy or 1 -ethyl-2- methylpropoxy.
  • Ci-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.
  • 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-C 4 -haloalkoxy is a Ci-C 4 -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-C 2 -Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHCI 2 , OCC , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2- fluoroethoxy, 2,2,2-trichloroethoxy or OC 2 F 5 .
  • Ci-C3-Haloalkoxy is additionally, for ex- ample, 2-
  • Ci-C 4 -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-brom pentoxy, 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 hydrogen atom is replaced by a Ci-C3-alkoxy group, as defined above.
  • Ci-C3-alkoxy-Ci-C 4 -alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C 4 -alkoxy group, as defined above.
  • Ci-C6-alkoxy-Ci-C6-alkyl refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, as defined above, where one hydrogen 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 -ethoxyethyl, 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-butoxyethyl, 2-sec-butoxyethyl, 2- isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1 -ethoxypropyl, 1 -propoxypropyl,
  • Ci-C4-alkoxy-methyl refers to methyl in which one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Ci-C6-alkoxy- methyl refers to methyl in which one hydrogen 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, hexyloxymethyl and the like.
  • Ci-C4-Haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen 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 hydrogen atoms (either in the alkoxy moiety or in the alkyl moiety or in both) are replaced by halogen atoms.
  • Examples are difluoro- methoxymethyl (CHF2OCH2), trifluoromethoxymethyl, 1 -difluoromethoxyethyl, 1 - trifluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl, difluoro- methoxymethyl (CH3OCF2), 1 ,1 -difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.
  • Pheny-Ci-C4-alkoxy is a Ci-C4-alkoxy group, as defined above, where one hydrogen atom has been replaced by a phenyl group. Examples are benzyloxy, 1 -phenylethoxy, 2-phenylethoxy, 1 -phenylpropoxy, 2-phenylpropoxy, 3-phenylpropoxy and the like.
  • the term "Ci-C2-alkylthio” is a Ci-C2-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C3-alkylthio is a Ci-C3-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C4-alkylthio is a Ci-C4-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C6-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 (iso- propylthio).
  • Ci-C4-Alkylthio is additionally, for example, butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio).
  • Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 -methylbutylthio,
  • Ci-Cs- Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
  • Ci-Cio-Alkylthio is additionally, for example, nonylthio, decylthio and positional isomers thereof.
  • Ci-C2-haloalkylthio is a Ci-C2-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C3-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-C 2 -Haloalkylthio is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C 2 -Haloalkylthio is, for example, SCH 2 F, SCHF 2 , SCF 3 , SCH 2 CI, SCHC , SCCI 3 , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 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-t
  • C1-C3- Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2- difluoropropylthio, 2,3-difluoropropylthio, 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-(CH2Br)-2-bromoethylthio.
  • Ci-C4-Haloalkylthio is additionally, for example, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio.
  • Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6- chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.
  • Ci-C2-a I ky Is u If i nyl is a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-alkylsulfinyl is a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C6-alkylsulfinyl is a C1-C6- alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • C1-C10- alkylsulfinyl is a Ci-Cio-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C2-Alkylsulfinyl is methylsulfinyl or ethylsulfinyl.
  • nyl is addi- tionally, for example, n-propylsulfinyl, 1 -methylethylsulfinyl (isopropylsulfinyl), butyl- sulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfi- nyl) or 1 ,1 -dimethylethylsulfinyl (tert-butylsulfinyl).
  • Ci-C6-Alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3- methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl,
  • Ci-Ce-Alkylsulfinyl is additionally, for example, heptylsulfinyl, octylsulfinyl, 2- ethylhexylsulfinyl and positional isomers thereof.
  • Ci-Cio-Alkylsulfinyl is additionally, for example, nonylsulfinyl, decylsulfinyl and positional isomers thereof.
  • the term "Ci-C2-haloalkylsulfinyl” is a Ci-C2-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • the term "Ci-C4-haloalkylsulfinyl” is a Ci-C4-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • C1-C6- haloalkylsulfinyl is a Ci-C6-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-Cio-haloalkylsulfinyl is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C2-Haloalkylsulfinyl is, for example, S(0)CH 2 F, S(0)CHF 2 , S(0)CF 3 , S(0)CH 2 CI, S(0)CHCI 2 , S(0)CCI 3 , chlorofluorome- thylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2- fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2- difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro- 2,2-difluoroethylsulfinyl, 2,2-dichloro-2-
  • Ci-C4-Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3- fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,
  • C1-C6- Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5- chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfi- nyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.
  • Ci-C 2 -alkylsulfonyl is a Ci-C 2 -alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C3-alkylsulfonyl is a Ci-C3-alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C4-alkylsulfonyl is a C1-C4- alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • C1-C6- alkylsulfonyl is a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-Cio-alkylsulfonyl is a Ci-Cio-alkyl group, as defined above, at- tached via a sulfonyl [S(0) 2 ] group.
  • Ci-C 2 -Alkylsulfonyl is methylsulfonyl or ethyl- sulfonyl.
  • Ci-C3-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or 1 - methylethylsulfonyl (isopropylsulfonyl).
  • Ci-C4-Alkylsulfonyl is additionally, for example, butylsulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobu- tylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert-butylsulfonyl).
  • Ci-C6-Alkylsulfonyl is addi- tionally, for example, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3- methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl,
  • d-Cs-Alkylsulfonyl is additionally, for example, heptylsulfonyl, octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.
  • Ci-Cio-Alkylsulfonyl is additionally, for example, nonylsulfonyl, decylsulfonyl and positional isomers thereof.
  • Ci-C 2 -haloalkylsulfonyl is a Ci-C 2 -haloalkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C3-haloalkylsulfonyl is a C1-C3- haloalkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci- C4-haloalkylsulfonyl is a Ci-C4-haloalkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C6-haloalkylsulfonyl is a Ci-C6-haloalkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • C1-C10- haloalkylsulfonyl is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C 2 -Haloalkylsulfonyl is, for example, S(0) 2 CH 2 F, S(0) 2 CHF 2 , S(0) 2 CF 3 , S(0) 2 CH 2 CI, S(0) 2 CHCI 2 , S(0) 2 CCI 3 , chlorofluoromethylsulfonyl, dichloro- fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2- chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2- difluoroethylsulfonyl, 2,2-d
  • Ci-C3-Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,
  • Ci-C 4 - Haloalkylsulfonyl is additionally, for example, 4-fluorobutylsulfonyl, 4- chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl.
  • C1-C6- Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl, 5- chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropen- tylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6- iodohexylsulfonyl or dodecafluorohexylsulfonyl.
  • Carboxyl is -C(0)OH.
  • Examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl and the like.
  • Ci-C6-haloalkylcarbonyl a Ci-C6-haloalkylcarbonyl
  • Ci-C 4 -haloalkylcarbonyl Ci-C 4 -haloalkylcarbonyl
  • Examples are trifluoromethylcarbonyl, 2,2,2- trifluoroethylcarbonyl and the like.
  • Examples are methoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, iso- propoxycarbonyl, n-butoxycarbonyl and the like.
  • Ci-C6-haloalkoxycarbonyl a Ci-C6-haloalkoxycarbonyl
  • Ci-C 4 -haloalkoxycarbonyl Ci-C 4 -haloalkoxycarbonyl
  • Examples are trifluoromethoxycarbonyl, 2,2,2- trifluoroethoxycarbonyl and the like.
  • Ci-C6-alkylamino is a group -N(H)Ci-C6-alkyl. Examples are methylamino, ethylamino, propylamino, isopropylamino, butylamino and the like.
  • di-(Ci-C6-alkyl)amino is a group -N(Ci-C6-alkyl)2. Examples are dimethyl- amino, diethylamino, ethylmethylamino, dipropylamino, diisopropylamino, methylprop- ylamino, methylisopropylamino, ethylpropylamino, ethylisopropylamino, dibutylamino and the like.
  • Ci-C6-alkylaminocarbonyl is a group -C(0)-N(H)Ci-C6-alkyl. Examples are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocar- bonyl, butylaminocarbonyl and the like.
  • di-(Ci-C6-alkyl)aminocarbonyl is a group -C(0)-N(Ci-C6-alkyl)2.
  • Examples are dimethylaminocarbonyl, diethylaminocarbonyl, ethylmethylaminocarbonyl, dipropyl- aminocarbonyl, diisopropylaminocarbonyl, methylpropylaminocarbonyl, methylisoprop- ylaminocarbonyl, ethylpropylaminocarbonyl, ethylisopropylaminocarbonyl, dibutyl- aminocarbonyl and the like.
  • 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 or 2 (or 3) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members denotes a 3-, 4-, 5- or 6- membered saturated, partially unsaturated or maximum unsaturated heteromonocyclic ring containing 1 or 2 (or 3) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members.
  • heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 denotes a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heteromonocyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, or a 7-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members.
  • heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 denotes a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximum unsaturated heter- omonocyclic ring or a 8-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members.
  • heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2 denotes a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximum unsaturated heteromonocyclic ring or a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members.
  • Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximally unsaturated 5-, 6- and 10- membered heterocyclic rings are aromatic. 7-, 8- and 9-membered rings cannot be aromatic. They are homoaromatic (7-membered ring, 3 double bonds) or are olefinic, having 4 double bonds (8- and 9-membered ring). The heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent. If the het- erocyclic ring is substituted, the substituent may be bound to a carbon or a nitrogen ring atom.
  • Examples of a 3-, 4-, 5- or 6-membered saturated heterocyclic ring include: Oxiranyl, thiiranyl, aziridinyl, diaziridinyl, oxetanyl, thietanyl, 1 -oxothietanyl, 1 ,1 -dioxothietanyl, azetidinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahy- drothien-3-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin- 3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1 -yl, imidazolidin-2-yl, imid
  • Examples of a 7- membered saturated heterocyclic ring include azepan-1 -, -2-, -3- or -4-yl, oxepan-2-, - 3-, -4- or -5-yl, hexahydro-1 ,3-diazepinyl, hexahydro-1 ,4-diazepinyl, hexahydro-1 ,3- oxazepinyl, hexahydro-1 ,4-oxazepinyl, hexahydro-1 ,3-dioxepinyl, hexahydro-1 ,4- dioxepinyl, and the like
  • Examples of an 8-membered saturated heterocyclic ring include azocanyl, oxocanyl and the like.
  • Examples of a 9-membered saturated heterocyclic ring include azonanyl, oxonanyl and the like.
  • Examples of a 10-membered saturated heterocyclic ring include azecanyl, oxecanyl and the like.
  • Examples of a 3-, 4-, 5- or 6-membered partially unsaturated heterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3- dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2- pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl,
  • Examples of a 7-membered partially unsaturated heterocyclic ring include 2,3,4,5- tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or
  • Examples of an 8-membered partially unsaturated heterocyclic ring include hexahydroazocine, tetrahydroazocine, dihydroazocine, hexahydrooxocine, tetrahydrooxocine, dihydrooxocine and the like.
  • Examples of a 9-membered partially unsaturated heterocyclic ring include hexahydroazonine, tetrahydroazonine, dihydro- azonine, hexahydrooxonine, tetrahydrooxonine, dihydrooxonine and the like.
  • Examples of a 10-membered partially unsaturated heterocyclic ring include hexahydroazecine, tetrahydroazecine, dihydroazecine, hexahydrooxecine, tetrahydrooxecine, dihydrooxe- cine and the like.
  • Examples for a 3-, 4-, 5-, 6- or 7-membered maximally unsaturated (including aromatic) heterocyclic ring are 5- or 6-membered heteroaromatic rings, such as 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 ,2,3-triazol-1 -yl, 1 ,2,3-triazol-2-yl, 1 ,2,3-triazol-4- yl, 1 ,3,4-triazol-1 -yl, 1 ,3,4-triazol-2-yl, 1 ,3,4-
  • Examples for an 8-membered maximally unsaturated heterocyclic ring are azocine, diazocine and the like.
  • Examples for a 9-membered maximally unsaturated heterocyclic ring are azonine, diazonine and the like.
  • Examples for a 10-membered maximally unsaturated heterocyclic ring are azecine, diazecine and the like.
  • Examples for 5- or 6-membered heteroaromatic monocyclic rings containing 1 , 2, 3 or 4 heteroatoms selected from O, N and S as ring members are 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 ,2,3-triazol-1 -yl, 1 ,2,3-triazol-2-yl, 1 ,2,3-triazol-4- yl, 1 ,3,4-triazol-1 -yl, 1 ,3,4-triazol-2-yl, 1 ,3,4-triazol-3-y
  • the "heterobicyclic rings” contain two rings which have at least one ring atom in common. At least one of the two rings contains a heteroatom or het- eroatom group selected from N, O, S, NO, SO and SO2 as ring member.
  • the term comprises condensed (fused) ring systems, in which the two rings have two neighboring ring atoms in common, as well as spiro systems, in which the rings have only one ring atom in common, and bridged systems with at least three ring atoms in common.
  • Examples for a 7-, 8-, 9- or 10-membered saturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
  • Examples for a 8-, 9- or 10-membered partially unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
  • Examples for a 8-, 9- or 10-membered maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
  • bridged 7-, 8-, 9- or 10-membered heterobicyclic rings containing 1 , 2 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, ring members are and the like.
  • # denotes the attachment point to the remainder of the molecule.
  • the attachment point is not restricted to the ring on which is shown, but can be on either of the fused rings, and may be on a carbon or on a nitrogen ring atom. If the rings carry one or more substituents, these may be bound to carbon and/or to nitrogen ring atoms.
  • Examples are, in addition to the saturated and partly unsaturated heteromonocyclic rings mentioned above, carbocyclic rings, such as cyclo- propyl, cyclopropanonyl, cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl, cy- clohexyl, cyclohexanonyl, cyclohexadienonyl, cycloheptyl, cycloheptanonyl, cyclooctyl, cyclooctanonyl, furan-2-onyl, pyrrolidine-2-onyl, pyrrolidine-2,5-dionyl, piperidine-2- only, piperidine-2,6-dionyl and the like.
  • carbocyclic rings such as cyclo- propyl, cyclopropanonyl, cyclobutyl, cyclobutanonyl, cyclopentyl,
  • B 1 and B 5 are CH
  • B 2 is CR 2 , where R 2 is not hydrogen
  • B 3 and B 4 are CR 2 , where R 2 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • B 2 is CR 2 , where R 2 is not hydrogen
  • B 4 is CR 2 , where R 2 has one of the above general meanings, or, in particular, one of the below preferred meanings
  • B 1 , B 3 , and B 5 are CH.
  • R 2 is selected from hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci- C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 , -OR 9 , -S(0) n R 9 and -N(R 10a )R 10b ,
  • R 8 , R 9 , R 10a and R 10b have one of the above general meanings, or, in particu- lar, one of the below preferred meanings.
  • R 2 is selected from hydrogen, halogen and Ci-C2-haloalkyl, in particular from hydrogen, F, CI, Br and CF3, and specifically from hydrogen, CF3 and CI.
  • G 1 is C-R 4b , where R 4b has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 4b is preferably selected from hydrogen, halogen and cyano, and is in particular hydrogen.
  • G 2 , G 3 and G 5 are preferably C-R 4 , where R 4 has one of the above general meanings, or, in particular, one of the below preferred meanings. More preferably, G 2 and G 5 are C-H and G 3 is C-R 4 , where R 4 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • G 4 is preferably C-R 4 or C-A, where R 4 and A have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 4 is preferably selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy, and more preferably from hydrogen, halogen and Ci-C4-haloalkyl.
  • R 4 is preferably not hydrogen.
  • R 4 is preferably selected from the group consisting of halogen, cyano, nitro, Ci-C6-alkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy, and more preferably from halogen and Ci-C 4 -haloalkyl. Specifically, R 4 is halogen if G 4 is C-R 4 .
  • R 9 is preferably selected from Ci- C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci- C4-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl, and more preferably from Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl and C3-Cs-cycloalkyl-Ci-C4-alkyl-.
  • R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocy- die ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkyn
  • R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl
  • R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • Ci-C6-alkyl and Ci-C6-haloalkyl are selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl and preferably from hydrogen and Ci-C6-alkyl;
  • R 14a and R 14b have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 14a is preferably selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and R 14b is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4 substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl,
  • ⁇ denotes the bonding point to the remainder of the molecule
  • k 0, 1 , 2 or 3,
  • q 0, 1 or 2;
  • each R 16a is independently hydrogen or is R 16 ;
  • each R 16 is independently selected from the group consisting of halogen, cyano, ni- tro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • R 14a is selected from hydrogen and methyl; and R 14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-methyl-, where the cycloalkyl moieties in the three last-mentioned radicals may carry a CN group; Ci-C6-alkyl substituted with a CN group, and a 4-membered saturated heterocyclic ring comprising one heteroatom or heteroatom group selected from
  • each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • each R 16 is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 14a is selected from hydrogen and methyl and is specifically hydrogen
  • R 14b is selected from hydrogen, Ci-C6-alkyl and Ci-Ce-haloalkyI.
  • N(R 10a )R 10b is specifically hydrogen.
  • R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl
  • R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 10a and R 10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4- alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3- C6-cycloalkylaminocarbonyl and C3-C6-halocycloalkylaminocarbonyl,
  • heterocyclic ring which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio.
  • R 10a and R 10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C4-alkylaminocarbonyl and Ci-C4-haloalkylaminocarbonyl; and are specifically hydrogen or Ci-C6-alkyl.
  • a 1 is N(R 5 )R 6 , wherein R 5 is selected from hydrogen and Ci-C6-alkyl; and
  • R 6 is N(R 10a )R 10b , wherein
  • R 10a is selected from hydrogen and Ci-C6-alkyl
  • R 13 is selected from the group consisting of hydrogen, halogen, C1-C6- alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the four last-mentioned aliphatic or cycloaliphatic radicals may be unsub- stituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from CN, C3-C4-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo.
  • A is A 2 .
  • W is preferably O.
  • Y is preferably N(R 5 )R 6 ; wherein R 5 and R 6 have one of the above general meanings, or, in particular, one of the below preferred meanings. More preferably, in A 2 , W is O and Y is N(R 5 )R 6 ; wherein R 5 and R 6 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 5 is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, where the 8 aforementioned aliphatic and cycloaliphatic radicals may be substituted by 1 , 2 or 3 radicals R 8 ; Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkoxycarbonyl and Ci-C4-haloalkoxycarbonyl; and
  • R 6 is preferably selected from hydrogen, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-C10- alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more substituents R 8 ,
  • phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R 11 , and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more substituents R 11 ;
  • R 8 , R 9 , R 10a , R 10b and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • N(R 5 )R 6 as a radical Y More preferably, in N(R 5 )R 6 as a radical Y,
  • R 5 is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, -Chb-CN, Ci-C6-alkoxy-methyl-, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl; and
  • R 8 and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings and wherein each R 9 is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, phenyl and - N(R 10a )R 10b , wherein R 10a and R 10b , independently of each other, are hydrogen or d-Ce-alkyl;
  • R 5 and R 6 together with the nitrogen atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated heteromonocyclic ring, where the ring may additionally contain 1 , 2 or 3 heteroatoms or heteroatom-containing groups selected from
  • heteromonocyclic or heterobicyclic ring may be substituted with 1 , 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and C1-C6- haloalkoxy;
  • R 5 is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkenyl, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl;
  • R 8 and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings;
  • R 5 and R 6 together with the nitrogen atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated heteromonocyclic ring, where the ring may additionally contain 1 , 2 or 3 heteroatoms or heteroatom-containing groups selected from
  • heteromonocyclic or heterobicyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; or
  • each R 9 is independently selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3- C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl-Ci-C4-alkyl.
  • R 8 as a substituent on an aliphatic or cycloaliphatic group is preferably selected from nitro, cyano, Cs-Cs-cycloalkyl which may be substituted by 1 or 2 substituents selected from CN, methyl and oxo, C 3 -Ce-halocycloalkyl, -OR 9 , -S(0) n R 9 ,
  • R 8 as a substituent on a cycloaliphatic group is additionally selected from C1-C6- alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl and C3-C6-cycloalkyl-Ci-C4-alkyl; and
  • R 9 , R 10a , R 10b , R 13 and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • N(R 5 )R 6 as a radical Y More preferably, in N(R 5 )R 6 as a radical Y,
  • R 8 as a substituent on a cycloaliphatic group is additionally selected from Ci-C6-alkyl and Ci-C6-haloalkyl;
  • R 9 , R 10a , R 10b , R 13 and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 10a and R 10b are preferably selected, independently of each other, from hydrogen, Ci- C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3- C6-cycloalkylaminocarbonyl and C3-C6-halocycloalkylaminocarbonyl,
  • heterocyclic ring which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio.
  • R 10a and R 10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci- C4-alkylaminocarbonyl and Ci-C4-haloalkylaminocarbonyl. Specifically, they are selected, independently of each other, from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl. Very specifically, one of R 10a and R 10b is hydrogen and the other is Ci-C4-alkyl or C1-C4- haloalkyl.
  • R 9 is preferably selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3- C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl, and more preferably from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
  • R 13 is preferably selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6- cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl and phenyl, and more preferably from Ci- C4-alkyl and Ci-C4-haloalkyl.
  • R 5 is selected from hydrogen and Ci-C4-alkyl
  • R 6 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries 1 or 2 radicals R 8 , C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl which carries one radical R 8 , where R 8 has one of the above general meanings, or, in particular, one of the above preferred meanings;
  • R 5 and R 6 together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heteromonocyclic ring, where the ring may further contain 1 , 2 or 3 heteroatoms or heteroatom-containing groups selected from NH and
  • C 0 as ring members, wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
  • substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
  • R 5 is hydrogen
  • R 6 is selected from Ci-C4-alkyl which carries 1 or 2 radicals R 8 , C3-C6-cycloalkyl, C3- C6-halocycloalkyl and C3-C6-cycloalkyl which carries one radical R 8 ; and specifically from methyl which carries 1 or 2 radicals R 8 , cyclopropyl, halocyclopropyl and cyclopropyl which carries one radical R 8 , where R 8 has one of the above general meanings, or, in particular, one of the above preferred meanings;
  • R 5 and R 6 together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heteromonocyclic ring, where the ring may further contain
  • heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
  • A is A 3 .
  • R 7a and R 7b in the group A 3 are independently of each other selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl, and more preferably one of R 7a and R 7b is hydrogen and the other is hydrogen or methyl. Specifically, both are hydrogen.
  • R 5 is preferably selected from hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radi- cals may be partially or fully halogenated and/or may be substituted with one or more substituents R 8 ; Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, C1-C4- alkoxycarbonyl and Ci-C4-haloalkoxycarbonyl; and
  • R 6 is preferably selected from hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radi- cals may be partially or fully halogenated and/or may be substituted by one or more substituents R 8 ,
  • R 8 , R 9 , R 10a , R 10b and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 5 is selected from hydrogen, Ci-C4-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, -CH2-CN, Ci-C6-alkoxy-methyl-, Ci-C4-alkylcarbonyl and Ci-C4-alkoxycarbonyl, and prefer- ably from hydrogen and Ci-C4-alkyl; and
  • R 8 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 9 , R 10a , R 10b , R 13 and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 10a and R 10b together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2- C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3- C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkylthio.
  • R 10a and R 10b in R 8 in the radicals R 5 and R 6 of the group A 3 are, inde- pendently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkyl substituted by one radical R 13 , C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ring comprising 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and SO2, as ring member, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy; and are specifically, independently of each other, selected from hydrogen, Ci-C4-
  • R 13 in R 8 in the radicals R 5 and R 6 of the group A 3 is preferably selected from CN, Ci- C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci- C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl and Ci-C6-haloalkylsulfonyl.
  • R 16 in R 8 in the radicals R 5 and R 6 of the group A 3 is preferably selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 10a and R 10b are selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and C3-C6-cycloalkyl;
  • R 13 is selected from CN, C3-C6-cycloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, phenyl and a heterocyclic ring selected from rings of formulae E-1 to E-54 as defined above; and
  • each R 16 as a substituent on heterocyclic rings of formulae E-1 to E-54 is independently selected from the group consisting of halogen, cyano, nitro, C1-C4- alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • R 10a and R 10b independently of each other, are selected from hydrogen and C1-C4- alkyl
  • R 13 is selected from cyano, C3-C6-cycloalkyl, phenyl, pyridinyl and pyrimidinyl. In an alternative embodiment of the invention, A is A 4 .
  • a 4 is preferably selected from a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2, 3 or 4 heteroa- toms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 11 , where R 11 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • a 4 is selected from a 3-, 4-, 5-, 6- or 7-membered saturated heteromonocyclic ring containing 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, a 5-, 6- or 7-membered partially unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, and a 5- or 6-membered aromatic heteromonocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring members, where the heteromonocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 11 , where R 11 has one of the above general meanings, or, in particular, one of the below preferred meanings.
  • a 4 is even more preferably selected from rings of formulae D-1 to D-173
  • ⁇ denotes the bonding point to the remainder of the molecule
  • k 0, 1 , 2 or 3;
  • q 0, 1 or 2;
  • each R 11a is independently hydrogen or has one of the general meanings given above or, in particular, one of the preferred meanings given below for R 11 ; and each R 11 has independently one of the above general, or, in particular, one of the below preferred meanings; and is preferably selected from D-59, D-65 and D-66 and is in particular D-59.
  • each R 11 is independently selected from the group consisting of halogen, cyano, ni- tro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • radicals A 1 , A 2 , A 3 and A 4 preference is given to A 2 .
  • R 1 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxycarbonyl, and more preferably from Ci-C4-haloalkyl and Ci-C4-alkoxycarbonyl.
  • R 1 is Ci-C4-haloalkyl, specifically Ci-C2-haloalkyl and more specifically halomethyl, in particular fluoromethyl, such as fluoromethyl, difluoromethyl and trifluoromethyl, and is very specifically trifluoromethyl.
  • R 3 is preferably selected from hydrogen, halogen and Ci-C4-alkyl, and is in particular hydrogen.
  • R 4a is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and
  • R 8 as a substituent on an aliphatic and cycloaliphatic radical R 4a is preferably selected from cyano, Ci-C4-alkoxy, Ci-C4-alkoxycarbonyl, phenyloxy and phenyl- Ci-C4-alkoxy-.
  • R 4a is selected from hydrogen or Ci-C6-alkyl.
  • Z is O.
  • R 8 , R 9 , R 10a , R 10b , R 11 , R 12 , R 13 , R 14 , R 14a , R 14b , R 15 and R 16 have following preferred meanings:
  • R 8 is a substituent on a cycloalkyi group, it is even more preferably selected from the group consisting of cyano, Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy and Ci- C3-haloalkoxy.
  • R 8 as a substituent on a cycloalkyi group is selected from cyano, Ci-C4-alkyl and Ci-C3-haloalkyl.
  • R 8 is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C6-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- Ce-alkynyl, C 2 -C 6 -haloalkynyl, -OR 9 , -SR 9 , -N(R 10a )R 10b , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or
  • R 8 is more preferably selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs- Cs-halocycloalkyl, d-Ce-alkoxy, Ci-C 6 -haloalkoxy, -N(R 10a )R 10b , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R 16 ; where R 10a , R 10b and R 16 have has one of the meaning
  • each R 9 is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkyl- Ci-C4-alkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 16 ; and a 3-, 4- , 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g. 1 , 2, 3 or 4, preferably 1 or 2, more preferably 1 , radicals R 16 , where R 16 has one of the meanings given above or in particular one of the preferred meanings given below.
  • each R 9 is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 16 ; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroa- toms selected from N , O and S, as ring members, where the heteroaromatic ring may be substituted by one or more radicals R 16 ; where R 16 has one of the meanings given above or in particular one of the preferred meanings given below.
  • R 10a and R 10b are, independently of each other, preferably selected from hydrogen, Ci- C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C 4 -alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C 4 -alkylaminocarbonyl, Ci-C 4 -haloalkylaminocarbonyl, C3-C6- cycloalkylaminocarbonyl, C3-C6-halocycloalkylaminocarbonyl, and a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heterocyclic
  • R 10a and R 10b together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N , O, S redesign NO, SO and S0 2 , as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN , Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 - C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C3-C6-cycloalkyl, C3- C6-halocycloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio and C
  • R 10a and R 10b are, independently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and a 3 or 4-membered saturated heterocyclic ring comprising 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and SO2, as ring member, where the heterocycl ' ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , sub- stituents selected from halogen, CN , Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci C4-haloalkoxy; and are specifically, independently of each other, selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
  • Each R 11 and each R 16 are independently of each occurrence and independently of each other preferably selected from halogen, CN , Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl, and more preferably from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • Each R 12 is preferably selected from Ci-C4-alkyl and is in particular methyl.
  • R 13 is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from the group consisting of cyano, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, -OH, - SH, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 13 is a substituent on a cycloalkyl group, it is preferably selected from the group consisting of cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, -OH, -SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and
  • R 13 is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy and Ci-C3-haloalkoxy.
  • R 13 as a substituent on a cycloalkyl group is selected from halogen, Ci-C4-alkyl and Ci-C3-haloalkyl.
  • R 8 is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs- Cs-cycloalkyl, C3-Cs-halocycloalkyl, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy and phe nyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 14 , R 14a and R 14b are, independently of each other, preferably selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and benzyl, where the phenyl ring in benzyl is optionally substituted 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • R 14a and R 14b together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy.
  • R 14 , R 14a and R 14b are, independently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and benzyl, where the phenyl ring in benzyl is optionally substituted 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy;
  • R 14a and R 14b together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy.
  • Each R 15 is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubsti- tuted and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy and Ci-C6-haloalkoxy.
  • Each R 16 is preferably selected from the group consisting of halogen, cyano, nitro, Ci- C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
  • each R 16 is independently selected from halogen, CN, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • the invention relates to a compound 1-1
  • R 21 , R 22 and R 23 independently of each other have one of the general or, in particular, one of the preferred meanings given above for R 2 ;
  • R 4a has one of the general or, in particular, one of the preferred meanings given above;
  • R 41 has one of the general or, in particular, one of the preferred meanings given above for R 4 ;
  • R A has one of the general or, in particular, one of the preferred meanings given above for R 4 or has one of the general or, in particular, one of the preferred meanings given above for A, and has specifically one of the preferred meanings given above for A.
  • R 21 , R 22 and R 23 are selected from hydrogen, halogen and Ci-C2-haloalkyl, preferably from hydrogen, F, CI, Br and CF3;
  • R 4a is hydrogen or Ci-C6-alkyl
  • R 41 is selected from the group consisting of hydrogen, halogen, cyano, nitro, Ci-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; and
  • R A is A 2 and in A 2 W is O and Y is -N(R 5 )R 6 ;
  • R 5 is selected from hydrogen and Ci-C4-alkyl
  • Ci-C6-alkyl is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries 1 or 2 radicals R 8 , C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl which carries one radical R 8 ; or
  • R 8 as a substituent on an aliphatic or cycloaliphatic group is selected from cyano, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, -OR 9 , -S(0) n R 9 ,
  • each R 16 is independently selected from halogen, CN, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; and
  • R 8 as a substituent on a cycloaliphatic group is additionally selected from d-Ce-alkyl and Ci-C 6 -haloalkyl;
  • R 9 , R 10a and R 10b are each independently selected from hydrogen, Ci-
  • R 13 is selected from Ci-C4-alkyl and Ci-C4-haloalkyl.
  • R 21 , R 22 and R 23 are selected from hydrogen, F, CI, Br R 4a is hydrogen or Ci-C6-alkyl;
  • R 41 is selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl and Ci-
  • R A is A 2 and in A 2 W is O and Y is -N(R 5 )R 6 ;
  • R 5 is hydrogen
  • R 6 is selected from Ci-C4-alkyl which carries 1 or 2 radicals R 8 , C3-C6- cycloalkyl, C3-C6-halocycloalkyl and C3-C6-cycloalkyl which carries one radical R 8 ; and specifically from methyl which carries 1 or 2 radicals R 8 , cyclo- propyl, halocyclopropyl and cyclopropyl which carries one radical R 8 ;
  • R 8 as a substituent on a cycloaliphatic group is additionally selected from Ci-C6-alkyl and Ci-C6-haloalkyl;
  • R 9 is selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl; and each R 16 is independently selected from halogen, CN , Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • the invention relates to a compound Z-l-1
  • R 21 , R 22 and R 23 independently of each other have one of the general or, in particular, one of the preferred meanings given above for R 2 ;
  • R 4a has one of the general or, in particular, one of the preferred meanings given
  • R 41 has one of the general or, in particular, one of the preferred meanings given
  • R A has one of the general or, in particular, one of the preferred meanings given
  • R 4 has one of the general or, in particular, one of the preferred meanings given above for A, and has specifically one of the preferred meanings given above for A.
  • R 21 , R 22 , R 23 , R 4a , R 41 and R 4 are as defined in the particular embodiment of compounds 1-1 .
  • R 21 , R 22 , R 23 , R 4a , R 41 and R 4 are as defined in the specific embodiment of compounds 1-1.
  • the invention relates to a compound E-l-1
  • R 21 , R 22 and R 23 independently of each other have one of the general or, in particular, one of the preferred meanings given above for R 2 ;
  • R 4a has one of the general or, in particular, one of the preferred meanings given
  • R 41 has one of the general or, in particular, one of the preferred meanings given
  • R A has one of the general or, in particular, one of the preferred meanings given
  • R 4 has one of the general or, in particular, one of the preferred meanings given above for A, and has specifically one of the preferred meanings given above for A.
  • compounds E-l-1 , R 21 , R 22 , R 23 , R 4a , R 41 and R 4 are as defined in the particular embodiment of compounds 1-1 .
  • compounds E-l-1 , R 21 , R 22 , R 23 , R 4a , R 41 and R 4 are as defined in the specific embodiment of compounds 1-1.
  • Examples of preferred compounds are compounds of the following formulae la.1 to la.60, where the variables have one of the general or preferred meanings given above.
  • Examples of preferred compounds are the individual compounds compiled in the tables 1 to 50400 below, Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6
  • R 5 is hydrogen
  • R 6 is CH(CH 3 )CF 3
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6
  • R 5 is hydrogen
  • R 6 is -CH2CH2OCH3
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6
  • R 5 is hydrogen
  • R 6 is -CH2CH2OCH2CH3
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6
  • R 5 is hydrogen
  • R 6 is -CH2CH2SCH2CH3
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6
  • R 5 is hydrogen
  • R 6 is -CH2CH2S(0)CH 2 CH3
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6
  • R 5 is hydrogen
  • R 6 is -ChbChbS D ⁇ CI-bCI-ls
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6
  • R 5 is hydrogen
  • R 6 is -CH(CH3)CH 2 S(0)CH3
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6
  • R 5 is hydrogen
  • R 6 is -C(CH3)2CH 2 S(0)2CH3
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6
  • R 5 is hydrogen
  • R 6 is cyclopropyl(4-chloro-3-(trifluoromethyl)-phenyl)methyl
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6 , wherein R 5 and R 6 , together with the nitrogen atom they are bound to, form aziridin-1 -yl
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6 , wherein R 5 and R 6 , together with the nitrogen atom they are bound to, form azetidin-1 -yl
  • R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6 , wherein R 5 and R 6 , together with the nitrogen atom they are bound to, form pyrrolidin-1 -yl
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6 , wherein R 5 and R 6 , together with the nitrogen atom they are bound to, form piperidin-1 -yl, and the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6 , wherein R 5 and R 6 , together with the nitrogen atom they are bound to, form piperazin-1 -yl
  • the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6 , wherein R 5 and R 6 , together with the nitrogen atom they are bound to, form 3,5-dioxopiperazin- 1 -yl
  • R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6 , wherein R 5 and R 6 , together with the nitrogen atom they are bound to, form 1 -methyl-2,6- dioxopiperazin-4-yl
  • R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • R 4a is hydrogen
  • R A is -C(0)N(R 5 )R 6 , wherein R 5 and R 6 , together with the nitrogen atom they are bound to, form morpholin-4-yl, and the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • Tables 841 to 1680 Compounds of the formula la.2 in which R 4a and R A are as defined in any of tables 1 to 840, and the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • Tables 16801 to 17640 Compounds of the formula la.21 in which R 4a and R A are as defined in any of tables 1 to 840, and the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • Tables 48721 to 49560 Compounds of the formula la.59 in which R 4a and R A are as defined in any of tables 1 to 840, and the combination of R 2a , R 2b and R 2c for a compound corresponds in each case to one row of Table A
  • the compounds of the formula (I) can be prepared by standard methods of organic chemistry, e.g. by the methods described hereinafter or in the synthesis descriptions of the working examples.
  • the substituents, variables and indices are as defined above for formula (I), if not otherwise specified.
  • A' is A or a precursor of A.
  • Compounds ⁇ , in which A' is a precursor of A can be converted as shown below into the different groups A 1 4 .
  • Compounds I wherein A is a group A 1 , wherein A 1 is -S(0) n R 9 or -N(R 5 )R 6 can for example be prepared by reacting a compound ⁇ wherein A is CI, Br or I in a Ullmann-type reaction with an amine NHR 5 R 6 or a thiol SHR 9 in the presence of a Cu(l) catalyst.
  • the thiol can then be oxi- dized, e.g. with hydrogen peroxide.
  • Amine groups can further be introduced in a Buch- wald-Hartwick reaction by reacting a compound ⁇ wherein A is CI, Br or I with an amine NHR 5 R 6 in the presence of a palladium catalyst, such as PdC (dppf) in the presence of a base, such as cesium carbonate.
  • Compounds I wherein A is a group A 2 , wherein W is O and Y is OR 9 can be prepared by reacting a compound ⁇ wherein A' is CI, Br, I or Otriflate with carbon monoxide in the presence of a palladium catalyst and an alcohol R 9 OH.
  • Compounds I wherein A is a group A 2 , wherein W is O and Y is NR 5 R 6 can be prepared by reacting a compound ⁇ wherein A' is CI, Br, I or Otriflate with carbon monoxide in the presence of a palladium catalyst and an alcohol ROH, wherein R is Ci-C4-alkyl, to a compound of formula 2.
  • Suitable palladium catalysts are for example those described in WO 201 1/161 130.
  • This ester is then hydrolyzed to the respective carboxylic acid, which is then reacted under standard amidation conditions with an amine NHR 5 R 6 .
  • Hydrolyzation can be carried out under standard conditions, e.g. under acidic conditions using for example hy- drochloric acid, sulfuric acid or trifluoroacetic acid, or under basic conditions using for example an alkali metal hydroxide, such as LiOH, NaOH or KOH.
  • Amidation is preferably carried out by activation of the carboxylic acids with oxalylchloride [(COCI)2] or thio- nylchloride (SOC ) to the respective acid chlorides, followed by reaction with an amine NHR 5 R 6 .
  • amidation is carried out in in the presence of a coupling reagent.
  • Suitable coupling reagent are well known and are for instance selected from carbodiimides, such as DCC (dicyclohexylcarbodiimide) and DCI (diisopropylcar- bodiimide), benzotriazol derivatives, such as HATU (0-(7-azabenzotriazol-1 -yl)- ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethyluronium hexafluorophosphate), HBTU ((O-benzotriazol-1 -yl)- ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethyluronium hexafluorophosphate) and HCTU (1 H-benzotriazolium-1 - [bis(dimethylamino)methylene]-5-chloro tetrafluoroborate) and phosphonium-derived activators, such as BOP ((benzotriazol-1 -
  • Lawesson's reagent CAS 19172-47-5
  • solvents such as HMPA or THF at an elevated temperature such as 60°C to 100°C can be used.
  • Preferred reaction conditions are THF at 65°C.
  • solvent free conditions or solvents such as toluene at temperatures such as 100°C to 200°C, preferably 140°C, are suitable reaction conditions.
  • Compounds I wherein A is a group A 3 , wherein R 7a and R 7b are hydrogen, can be prepared from a compound 4.
  • the alcohol 4 can be prepared from the protected analogue 3, wherein PG stands for a protecting group, for example a silyl protecting group such as trimethyl silyl or tert.-butyldimethylsilyl, as shown in scheme 1 .
  • the alkohol 4 can be prepared from the aldehyde 1 by reduction for example with sodium borohydride.
  • the OH group can first be converted into a better leaving group, e.g. into a sulfonate (for exam- pie mesylate, tosylate or a triflate group).
  • R 6 is a group -C(0)R 8
  • R 7a and R 7b are optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl or optionally substituted alkynyl, can be obtained from an alcohol of formula 5.
  • the alcohol 5 can be prepared from the protected analogue, wherein the OH group is protected, for example, by a silyl protecting group such as trimethyl silyl or tert.-butyldimethylsilyl.
  • Alcohol 5 can then be converted into amine 6 via the corresponding azide, as described, for example, in Organic Letters, 2001 , 3(20), 3145-3148.
  • Compounds I wherein A is A 4 can be prepared by standard ring coupling reactions.
  • compounds wherein A 4 is an N-bound heterocyclic ring can be prepared by reacting a compound ⁇ wherein A is CI, Br or I with the respective ring A 4 -H (H being on the nitrogen ring atom to be coupled) under Ullmann coupling conditions, such as described, for example, in WO 2007/075459.
  • copper(l) iodide or copper(l) oxide and a ligand such as 1 ,2-cyclohexyldiamine is used, see for example Kanemasa et al., European Journal of Organic Chemistry, 2004, 695-709.
  • A' is F
  • the reaction is typically run in a polar aprotic solvent such as ⁇ , ⁇ -dimethylformamide, N,N- dimethylacetamide or N-methylpyrrolidone, and in the presence of an inorganic base such as sodium, potassium or cesium carbonate.
  • a 4 is a C-bound heterocyclic ring
  • a typical catalyst is tetrakis(triphenylphosphine)palladium(0).
  • Solvents such as tetrahy- drofuran, acetonitrile, diethyl ether and dioxane are suitable.
  • the boronic acids A 4 - B(OH)2 are either commercially available or can be prepared by known methods.
  • Other methods for introduction of the heterocyclic groups A 4 are the Heck, Stille, Kumada and Buchwald-Hartwig coupling procedures; see for example Tetrahedron, 2004, 60, 8991 - 9016.
  • reaction can be performed using a Lewis acid, such as titanium tetrachloride, and an amine, such as triethylamine, diisopropylethylamine or tetramethylethylenediamine ("TMEDA").
  • a Lewis acid such as titanium tetrachloride
  • an amine such as triethylamine, diisopropylethylamine or tetramethylethylenediamine (“TMEDA"
  • the intermediate is treated with a ketone of formula 12 and a base, such as n-butyl lithium, sodium hydride or potassium tert- butoxide.
  • a base such as n-butyl lithium, sodium hydride or potassium tert- butoxide.
  • the compounds of formula I or ⁇ wherein R 3 is H and Z is oxygen can be prepared using a Horner-Wadsworth-Emmons reaction.
  • the ⁇ -ketophosphonate is synthesized from the alkyl ester 13 and methyl dialkyi phosphonate.
  • Such halogenated compounds are described, for example, in WO 2005/035497.
  • the intermediate is treated with a ketone of formula 12 to yield compound I or ⁇ ; see scheme 4.
  • Such Horner-Wadsworth-Emmons reaction are described, for example, in Journal of Medicinal Chemistry, 36, 1993, 2984-2997.
  • the protected alcohol of formula 19 can be prepared in a similar way from the reduced precusor; see scheme 6.
  • the compounds of formula (I) including their stereoisomers, salts, and N- oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds (I) or the respective precursor or by customary modifications of the synthesis routes described. For exam- pie, in individual cases, certain compounds of formula (I) can advantageously be prepared from other compounds of formula (I) by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.
  • reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel.
  • Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or trituration. Due to their excellent activity, the compounds of the present invention may be used for controlling invertebrate pests.
  • the present invention also provides a method for 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 pesticidally effective amount of a compound of the present invention or a composition as defined above.
  • the invention also relates to the use of a compound of the invention, of a stereoisomer and/or of an agriculturally or veterinarily acceptable salt thereof for combating invertebrate pests
  • the method of the invention serves for protecting plant propagation material (such as seed) and the plant which grows therefrom from invertebrate pest attack or infestation and comprises treating the plant propagation material (such as seed) with a pesticidally effective amount of a compound of the present invention as defined above or with a pesticidally effective amount of an agricultural composition as defined above and below.
  • the method of the invention is not limited to the protection of the "sub- strate" (plant, plant propagation materials, soil material etc.) which has been treated according to the invention, but also has a preventive effect, thus, for example, according protection to a plant which grows from a treated plant propagation materials (such as seed), the plant itself not having been treated.
  • the method of the invention serves for protecting plants from attack or infestation by invertebrate pests, which method comprises treating the plants with a pesticidally effective amount of at least one compound of the invention, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.
  • invertebrate pests are preferably selected from arthropods and nematodes, more preferably from harmful insects, arachnids and nematodes, and even more preferably from insects, acarids and nematodes.
  • invertebrate pests are most preferably insects.
  • the invention further provides an agricultural composition for combating invertebrate pests, which comprises such an amount of at least one compound according to the invention and at least one inert liquid and/or solid agronomically acceptable carrier that has a pesticidal action and, if desired, at least one surfactant.
  • Such a composition may comprise a single active compound of the present invention or a mixture of several active compounds of the present invention.
  • the composition according to the present invention may comprise an individual isomer or mixtures of isomers or a salt as well as individual tautomers or mixtures of tautomers.
  • the compounds of the present invention, including their salts, stereoisomers and tautomers, are in particular suitable for efficiently controlling arthropodal pests such as arachnids, myriapedes and insects as well as nematodes.
  • insects from the order of the lepidopterans for example Acronicta major, Adoxophyes orana, Aedia leucomelas, Agrotis spp.
  • Chilo suppressalis such as Chilo suppressalis; Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Clysia am- biguella, Cnaphalocerus spp., Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Ephestia cautella, Ephestia kuehniella, Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Feltia spp.
  • Feltia subterranean such as Feltia subterranean; Galleria mellonella, Grapho- litha funebrana, Grapholitha molesta, Helicoverpa spp. such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such as Heliothis armigera, Heliothis virescens, Helio- this zea; Hellula undalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homona magnanima, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma spp.
  • Lymantria spp. such as Lymantria dispar, Lymantria monacha; Lyonetia clerkella, Malacosoma neustria, Mamestra spp. such as Mamestra brassicae; Mocis repanda, Mythimna separata, Or- gyia pseudotsugata, Oria spp., Ostrinia spp.
  • Pseudoplu- sia includens, Pyrausta nubilalis, Rhyacionia frustrana, Scrobipalpula absolutea, Sitotro- ga cerealella, Sparganothis pilleriana, Spodoptera spp.
  • Atomaria linearis such as Atomaria linearis; Attagenus spp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as Bruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus betulae, Callosobruchus chinensis, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp.
  • Leptinotarsa decemlineata such as Leptinotarsa decemlineata; Limonius californicus, Lissorhoptrus oryzophilus, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp. such as Lyctus bruneus; Melanotus communis, Meligethes spp. such as Meligethes aeneus; Melolontha hippocastani, Melolontha melolontha, Migdolus spp., Monochamus spp.
  • Phyllotreta chrysocephala such as Phyllotreta chrysocephala, Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp., Phyllopertha horticola, Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis , Rhizopertha dominica, Sitona lineatus, Sitophilus spp. such as Sitophilus granaria, Sitophilus zeamais; Sphenophorus spp. such as Sphenophorus levis; Sternechus spp.
  • Aedes spp. such as Aedes aegypti, Aedes albopictus, Aedes vexans; Anastrepha ludens, Anopheles spp.
  • Anopheles albimanus such as Anopheles albimanus, Anopheles crucians, Anopheles freeborni, Anopheles gambiae, Anopheles leucosphy- rus, Anopheles maculipennis, Anopheles minimus, Anopheles quadrimaculatus, Anopheles sinensis; Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Cerafitis capitata, Ceratitis capitata, Chrysomyia spp.
  • Chrysomya bezziana such as Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria; Chrysops atlanticus, Chrysops discal- is, Chrysops silacea, Cochliomyia spp. such as Cochliomyia hominivorax; Contarinia spp. such as Contarinia sorghicola; Cordylobia anthropophaga, Culex spp.
  • Lucilia caprina such as Lucilia caprina, Lucilia cuprina, Lucilia serica- ta; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. such as Mayetiola destructor; Musca spp. such as Musca autumnalis, Musca domestica; Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyza florum, Oscinella spp. such as Oscinella frit; Pe- gomya hysocyami, Phlebotomus argentipes, Phorbia spp.
  • Phorbia antiqua Phorbia brassicae, Phorbia coarctata
  • Prosimulium mixtum Psila rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis cerasi, Rhagoletis pomonella
  • Sarcophaga spp. such as Sarcophaga haemorrhoidalis
  • Simulium vittatum Stomoxys spp. such as Stomoxys calcitrans
  • Thrips spp. such as Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici
  • Heliothrips spp. Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp. such as Scirtothrips citri
  • Taeni- othrips cardamoni Thrips spp.
  • Thrips oryzae Thrips palmi
  • Thrips tabaci termites (Isoptera), e.g.
  • Calotermes flavicollis Coptotermes formosanus, Heterotermes aureus, Heterotermes longiceps, Heterotermes tenuis, Leucotermes flavipes, Odonto- termes spp., Reticulitermes spp. such as Reticulitermes speratus, Reticulitermes fla- vipes, Reticulitermes grassei, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes virginicus; Termes natalensis, cockroaches (Blattaria - Blattodea), e.g.
  • Aphis fabae such as Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis grossu- lariae, Aphis pomi, Aphis sambuci, Aphis schneideri, Aphis spiraecola; Arboridia apica- lis, Arilus critatus, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp. such as Bemisia argentifolii, Bemisia tabaci; Blissus spp.
  • Dysaphis plantaginea such as Dysaphis plantaginea, Dysaphis pyri, Dysaphis radicola; Dysau- lacorthum pseudosolani, Dysdercus spp. such as Dysdercus cingulatus, Dysdercus intermedius; Dysmicoccus spp., Empoasca spp. such as Empoasca fabae, Empoasca solana; Eriosoma spp., Erythroneura spp., Eurygaster spp. such as Eurygaster integri- ceps; Euscelis bilobatus, Euschistus spp.
  • Euschistuos heros such as Euschistuos heros, Euschistus im- pictiventris, Euschistus servus; Geococcus coffeae, Halyomorpha spp. such as Halyo- morpha halys; Heliopeltis spp., Homalodisca coagulata, Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, lcerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Leptocorisa spp., Leptoglossus phyl- lopus, Lipaphis erysimi, Lygus spp.
  • Macrosiphum spp. such as Macrosiphum rosae, Ma- crosiphum avenae, Macrosiphum euphorbiae; Mahanarva fimbriolata, Megacopta cri- braria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Metcafiella spp., Metopolophium dirhodum, Miridae spp., Monellia costalis, Monelliopsis pecanis, Myzus spp.
  • Nezara spp. such as Nezara viridula; Nilaparvata lugens, Oebalus spp., Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp.
  • Piezodorus guildinii Pinnaspis aspidistrae, Planococcus spp., Proto- pulvinaria pyriformis, Psallus seriatus, Pseudacysta persea, Pseudaulacaspis pentago- na, Pseudococcus spp. such as Pseudococcus comstocki; Psylla spp.
  • Psylla mali Psylla piri
  • Pteromalus spp. Pyrilla spp.
  • Quadraspidiotus spp. Quesada gigas
  • Rastrococcus spp. Reduvius senilis
  • Rhodnius spp. Rhopalomyzus ascalonicus
  • Rhopalosiphum pseudobrassicas such as Rhopalosiphum pseudobrassicas, Rhopalosiphum insertum, Rhopalosiphum maidis, Rhopalosiphum padi; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaphoides titanus, Schizaphis gra- minum, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Solubea insularis , Stephanitis nashi, Sticto- cephala festina, Tenalaphara malayensis, Thyanta spp.
  • Thyanta perditor such as Thyanta perditor; Ti- braca spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp. such as Toxoptera aurantii; Trialeurodes spp. such as Trialeurodes vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as Unaspis yanonensis; and Viteus vitifolii, ants, bees, wasps, sawflies (Hymenoptera), e.g.
  • Atta capiguara Atta cephalotes, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Bombus spp., Camponotus floridanus, Crematogaster spp., Dasymutilla occidentalis, Diprion spp., Dolichovespula maculata, Hoplocampa spp. such as Hoplocampa minuta, Hoplocampa testudinea; Lasius spp.
  • Amblyomma spp. e.g. Amblyomma americanum, Amblyomma var- iegatum, Amblyomma maculatum
  • Argas spp. e.g. Argas persicus
  • Boophilus spp. e.g. Boophilus annulatus, Boophilus decoloratus, Boophilus microplus
  • Dermacentor silvarum, Dermacentor andersoni Dermacentor variabilis
  • Hyalomma spp. e.g. Hy- alomma truncatum
  • Ixodes spp. e.g.
  • Sarcoptes spp. e.g. Sarcoptes scabiei
  • Eriophyidae spp. such as Acaria sheldoni, Aculops spp. (e.g. Aculops pelekassi) Aculus spp. (e.g. Aculus
  • Tenuipalpi- dae spp. such as Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp.
  • Eotetranychus spp. such as Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Tetranychus cin- nabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae; Bryobia praetiosa, Panonychus spp. (e.g. Panonychus ulmi, Panonychus citri), Metatetranychus spp. and Oligonychus spp. (e.g. Oligonychus pratensis), Vasates lycopersici; Araneida, e.g.
  • Geophilus spp. Scutigera spp. such as Scutigera coleop- trata; millipedes (Diplopoda), e.g. Blaniulus guttulatus, Narceus spp.,
  • Earwigs e.g. forficula auricularia, lice (Phthiraptera), e.g. Damalinia spp., Pediculus spp. such as Pediculus humanus capitis, Pediculus humanus corporis; Pthirus pubis, Haematopinus spp. such as Hae- matopinus eurysternus, Haematopinus suis; Linognathus spp.
  • Linognathus vituli such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp., springtails (Collembola ), e.g. Onychiurus ssp. such as Onychiurus armatus,
  • nematodes plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javani- ca, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, An- guina species; Stem and foliar nematodes, Aphelenchoides species such as Aphelen- choides besseyi ; Sting nematodes, Belonolaimus longicaudatus and other Belono- laimus species; Pine nematodes, Bursaphelenchus lignicolus Mamiy
  • Radopholus species Reniform nematodes, Rotylenchus robustus, Rotylenchus reni- formis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylencho- rhynchus species; Citrus nematodes, Tylenchulus species such as Tylenchulus semi- penetrans; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.
  • Examples of further pest species which may be controlled by compounds of fomula (I) include: from the class of the Bivalva, for example, Dreissena spp.; from the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum,
  • Diloboderus abderus such as Diloboderus abderus; Edessa spp., Epinotia spp., Formicidae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor, Hydrel- lia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta , Leptocorsia oratorius , Liogenys fuscus, Lucillia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Marasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipter- us, Microtheca spp., Mocis latipes, Murgantia spp., My
  • Orseolia oryzae such as Orseolia oryzae; Ox- ycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp, Pro- cornitermes triacifer , Psylloides spp., Rachiplusia spp., Rhodopholus spp., Scaptocoris castanea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas , Scirpophaga innotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp.
  • Sesamia inferens such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata, Spissistilus spp., Stalk borer, Stenchaetothrips biformis, Steneotarsonemus spinki, Sylepta deroga- ta, Telehin licus, Trichostrongylus spp..
  • insects preferably sucking or piercing and chewing and biting insects such as insects from the genera Lepidoptera, Coleoptera and Hemiptera, in particular Lepidoptera, Coleoptera and true bugs.
  • the compounds of the present invention are moreover useful for controlling insects of the orders Thysanoptera, Diptera (especially flies, mosquitos), Hymenoptera (especially ants) and Isoptera (especially termites.
  • the compounds of the present invention are particularly useful for controlling insects of the orders Lepidoptera and Coleoptera.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
  • An agrochemical composition comprises a pesticidally effective amount of a compound I.
  • effective amount denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the species to be controlled, the treated cultivated plant or material, the climat- ic conditions and the specific compound I used.
  • compositions e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6 th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F In- forma, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dis- persants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec- tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffin, tetra- hydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. toluene, paraffin, tetra- hydronaphthalene, alkylated
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phospho- nates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e.g. cellulose, starch
  • fertilizers
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof.
  • Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in
  • McCutcheon's, Vol.1 Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sul- fonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccin- ates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinyl- alcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of poly- ethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or pol- ybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers.
  • polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothia- zolinones and benzisothiazolinones.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne des composés (het)arylalcényle de formule (I), les variables étant telles que définies dans les revendications et la description. Les composés sont utiles pour combattre des nuisibles invertébrés, en particulier les arthropodes et les nématodes nuisibles, ou pour les maîtriser. La présente invention porte également sur un procédé de lutte contre les nuisibles invertébrés à l'aide de ces composés, sur un matériel de propagation végétale, sur une composition agricole et sur une composition vétérinaire comprenant lesdits composés.
PCT/EP2015/050693 2014-01-16 2015-01-15 Composés (het)arylalcényle et leur utilisation pour lutter contre les nuisibles invertébrés WO2015107117A1 (fr)

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Cited By (4)

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Publication number Priority date Publication date Assignee Title
EP3241830A1 (fr) 2016-05-04 2017-11-08 Bayer CropScience Aktiengesellschaft Derivés de bicycles condensés hétérocycliques utilisés comme pesticides
WO2018033455A1 (fr) 2016-08-15 2018-02-22 Bayer Cropscience Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
WO2018197257A1 (fr) 2017-04-24 2018-11-01 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
WO2019162174A1 (fr) 2018-02-21 2019-08-29 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides

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EP1975149A1 (fr) * 2005-12-26 2008-10-01 Nissan Chemical Industries, Ltd. Compose de 1,3-bis(phenyle substitue)-3-hydroxypropan-1-one ou 2-propen-1-one et son sel
WO2012119984A1 (fr) * 2011-03-09 2012-09-13 Bayer Cropscience Ag Amides d'acide carboxylique d'indole et de benzimidazole utilisés comme insecticides et acaricides
WO2013149940A1 (fr) * 2012-04-02 2013-10-10 Basf Se Composés acrylamides pour lutter contre des animaux nuisibles invertébrés
WO2013174645A1 (fr) * 2012-05-24 2013-11-28 Basf Se Composés de n-thioanthranilamide et leur utilisation comme pesticides

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1975149A1 (fr) * 2005-12-26 2008-10-01 Nissan Chemical Industries, Ltd. Compose de 1,3-bis(phenyle substitue)-3-hydroxypropan-1-one ou 2-propen-1-one et son sel
WO2012119984A1 (fr) * 2011-03-09 2012-09-13 Bayer Cropscience Ag Amides d'acide carboxylique d'indole et de benzimidazole utilisés comme insecticides et acaricides
WO2013149940A1 (fr) * 2012-04-02 2013-10-10 Basf Se Composés acrylamides pour lutter contre des animaux nuisibles invertébrés
WO2013174645A1 (fr) * 2012-05-24 2013-11-28 Basf Se Composés de n-thioanthranilamide et leur utilisation comme pesticides

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XIAOQIAN SUN ET AL: "Formation of Functionalized 2 H -Azirines through PhIO-Mediated Trifluoroethoxylation and Azirination of Enamines", ORGANIC LETTERS, vol. 15, no. 24, 20 December 2013 (2013-12-20), pages 6222 - 6225, XP055175822, ISSN: 1523-7060, DOI: 10.1021/ol4030716 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3241830A1 (fr) 2016-05-04 2017-11-08 Bayer CropScience Aktiengesellschaft Derivés de bicycles condensés hétérocycliques utilisés comme pesticides
WO2018033455A1 (fr) 2016-08-15 2018-02-22 Bayer Cropscience Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
WO2018197257A1 (fr) 2017-04-24 2018-11-01 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
WO2019162174A1 (fr) 2018-02-21 2019-08-29 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides

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