WO2014206911A1 - Isothiazoline compounds for combating invertebrate pests - Google Patents

Isothiazoline compounds for combating invertebrate pests Download PDF

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Publication number
WO2014206911A1
WO2014206911A1 PCT/EP2014/063106 EP2014063106W WO2014206911A1 WO 2014206911 A1 WO2014206911 A1 WO 2014206911A1 EP 2014063106 W EP2014063106 W EP 2014063106W WO 2014206911 A1 WO2014206911 A1 WO 2014206911A1
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Prior art keywords
alkyl
cycloalkyl
group
radicals
ring
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English (en)
French (fr)
Inventor
Pascal BINDSCHÄDLER
Wolfgang Von Deyn
Karsten KÖRBER
Deborah L. Culbertson
Franz Josef Braun
Koshi Gunjima
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BASF SE
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BASF SE
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Priority to EP14732176.4A priority Critical patent/EP3013819B1/en
Priority to CA2916766A priority patent/CA2916766C/en
Priority to JP2016522423A priority patent/JP2016527208A/ja
Priority to BR112015032346A priority patent/BR112015032346A2/pt
Priority to CN201480043338.3A priority patent/CN105473582A/zh
Priority to ES14732176.4T priority patent/ES2688893T3/es
Priority to MX2015018015A priority patent/MX368592B/es
Publication of WO2014206911A1 publication Critical patent/WO2014206911A1/en
Anticipated expiration legal-status Critical
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    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems

Definitions

  • Isothiazoline compounds for combating invertebrate pests Description
  • the present invention relates to isothiazoline 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 isothiazoline compounds of formula I
  • B 1 , B 2 and B 3 are each independently selected from the group consisting of N and CR 2 , with the proviso that at most two of B 1 , B 2 and B 3 are N;
  • G 1 , G 2 , G 3 and G 4 are each independently selected from the group consisting of N and CR 4 , with the proviso that at most two of G 1 , G 2 , G 3 and G 4 are N;
  • W is O or S
  • 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 heteromono- or heterobicyclic ring may be substituted by one or more radicals R 11 ;
  • R 3a , R 3b are each independently selected from the group consisting of hydrogen, halogen, hydroxyl, -C0 2 R 3d , Ci-C 3 -alkyl, d-C 3 -haloalkyl, C 2 -C 3 -alkenyl, C 2 -C 3 - alkynyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkylthio, Ci-C3-haloalkylthio, Ci-
  • R 3d is selected from the group consisting of hydrogen, Ci-C6-alkyl and C1-C3- alkyloxy-Ci-C3-alkyl-; each R 4 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 , C3-C8- cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R 8 , C2-C6-alkynyl which 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 ;
  • 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 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 ; and additionally or alternatively, two radicals R 7 present on the same carbon atom of the 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10- membered saturated, partially unsaturated or maximally unsaturated
  • 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 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
  • R 8 as a substituent on a cycloalkyi ring is additionally selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in these six radicals may be substituted by one or more radicals R 13 ; and
  • each R 9 is independently selected from the group consisting of hydrogen, cyano, Ci- Ce-alkyl, Ci-C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-Ci-C 4 -alkyl-, C 3 -C 8 - halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine 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 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 heterocyclic ring is optionally substituted with one or more substituents R 16 ; and 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- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight 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 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 substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-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- haloalkynyl, phenyl, optionally substituted with 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 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 optionally carries one or more substituents R 16 ;
  • phenyl optionally substituted with 1 , 2, 3, 4, or 5 substituents selected
  • 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 12 is independently selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2- C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, and phenyl, optionally substituted with 1 , 2, 3, 4, or 5 substituents R 16 ;
  • R 13 is independently selected from the group consisting of cyano, nitro,
  • 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, phenoxy, where the phenyl moiety in the three 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 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 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 ; 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-
  • 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, C1-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, C1-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;
  • C3-C 0 -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, C1-C4- alkoxy, Ci-C4-haloalkoxy 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, C1-C6- haloalkoxy and (Ci-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-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; each n is independently 0, 1 or 2; and
  • each m is independently 0 or 1 ; and the N-oxides, stereoisomers and agriculturally or veterinarily acceptable salts thereof; except for compounds I wherein B 1 and B 3 are C-CI, and simultaneously B 2 is C-H, G 1 , G 3 and G 4 are C-H, G 2 is C-F, C-CI, C-CH 3 or C-SCH3, W is O, R 1 is CF 3 , R 3a and R 3b are H, and R 5 and R 6 , together with the nitrogen atom they are bound to, form a ring selected from aziridin-1 -yl, azetidin-1 -yl, pyrrolidin-1 -yl, piperidin-1 -yl, thiazolidin-3-yl, morpholin-4-yl, thiomorpholin-4-yl, 1 -oxo-1 ,4-thiazinan-4-yl and 1 ,1 -dioxo-1 ,4-thiazinan- 4-
  • the present invention also provides an agricultural composition comprising at least one compound of the formula I as defined herein and/or an agriculturally acceptable salt thereof and at least one liquid and/or solid agriculturally acceptable carrier.
  • the present invention also provides a veterinary composition comprising at least one compound of the formula I as defined herein and/or a veterinarily acceptable salt thereof and at least one liquid and/or solid veterinarily 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.
  • 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 a compound of the formula I or a 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.
  • steroisomers 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).
  • 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.
  • One center of chirality is the carbon ring atom of the isothiazoline ring carrying radical R 1 .
  • the invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures.
  • Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
  • N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO). To be more precise, it relates to any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • N-oxides of compounds I can in particular be prepared by oxidizing e.g. the ring nitrogen atom of the isothiazoline moiety and/or, if G 1 , G 2 , G 3 or G 4 is N, this nitrogen atom, and/or of the ring formed by R 5 and R 6 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-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammoni
  • 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 butyrate. 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 hydrochlorids, 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 hydrochlorids, sulphates, phosphates, and nitrates
  • salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
  • invertebrate pest encompasses animal populations, such as 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.
  • 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. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
  • auxin herbicides
  • herbicides e. bromoxynil or ioxynil herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • ALS inhibitors e.g. described in Pest Managem. Sci.
  • cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, 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.
  • VIP1 , VIP2, VIP3 or VIP3A vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins;
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize- RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxy- steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases.
  • RIP ribosome-inactivating proteins
  • RIP ribosome-inactivating proteins
  • steroid metabolism enzymes such as 3-hydroxy
  • 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 tolerance 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 synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum
  • T4-lysozym e. g. potato cultiv
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • 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 particular fluorine, chlorine or bromine.
  • alkyl as used herein and in the alkyl moieties of alkoxy, alkylthio, alkylsulfinyl, 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 (“Ci-C 3 -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-C 2 -Alkyl is methyl or ethyl.
  • d-Cs-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-methyl butyl, 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 -ethyl-2
  • 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,
  • Ci-C3-haloalkyl is additionally, for example, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1 ,1 - difluoropropyl, 2,2-difluoropropyl, 1 ,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3- trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trifluoroprop-2-yl, 3-chloropropyl and the like.
  • Examples for Ci-C4-haloalkyl are, apart those mentioned for Ci-C3-haloalkyl, 4- chlorobutyl and the like.
  • Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl,
  • dichloromethyl trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl 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 (“C 2 -C8-alkynyl”), or 2 to 10 (“C 2 -Cio-alkynyl”) carbon atoms and one or two triple bonds in any position, for example C 2 -C3-alkynyl, such as ethynyl, 1 -propynyl or 2- propynyl; C 2 -C 4 -alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl and the like, C
  • 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 (“C 2 -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 having 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1 ]octyl.
  • the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
  • halocycloalkyl as used herein, which is also expressed as “cycloalkyl which is partially or fully halogenated”, refers to mono- or bi- or polycyclic saturated hydrocarbon groups having 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”) carbon 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.
  • 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 cycloalkyl 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 cyclopropylmethyl, cyclopropylethyl, cyclopropyl propyl, cyclobutylmethyl, cyclobutylethyl 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,
  • C3-C8-cycloalkyl-Ci-C 4 -alkyl apart those mentioned for C3-C6-cycloalkyl-Ci-C 4 -alkyl, are cycloheptylmethyl, cycloheptylethyl, cyclooctylmethyl and the like.
  • C3-C8-halocycloalkyl-Ci-C 4 -alkyl refers to a Cs-Cs-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C 4 -alkyl group, as defined above.
  • cycloalkenyl refers to monocyclic hydrocarbon radicals with at least one C-C double bond in the ring, which ring is however not aromatic, the hydrocarbon radicals having 3 to 8 (“Cs-Cs-cycloalkyl) carbon atoms.
  • Examples are cyclopropenyl, such as cycloprop-1 -enyl and cycloprop-2-yl, cyclobutenyl, such as cyclobut-1 -enyl and cyclobut-2-enyl, cyclopentenyl, such as cyclopent-1 -enyl, cyclopent-2-enyl and cyclopent-3-enyl, cyclopentadienyl, such as cyclopenta-1 ,3- dienyl, cyclpenta-1 ,4-dienyl and cyclpenta-2,4-dienyl, cyclohexenyl, such as cyclohex- 1 -enyl, cyclohex-2-enyl and cyclohex-3-enyl, cyclohexadienyl, such as cyclohexa-1 ,3- dienyl, cyclohexa-1 ,4-dienyl, cyclohe
  • halocycloalkenyl refers to monocyclic hydrocarbon radicals with at least one C-C double bond in the ring, which ring is however not aromatic, the hydrocarbon radicals having 3 to 8 (“Cs-Cs-halocycloalkenyl”) carbon atoms, and wherein some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • Ci-C2-alkoxy is a Ci-C2-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C3-alkoxy is a Ci-C3-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C4-alkoxy is a Ci-C4-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C6-alkoxy is a Ci-C6-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-Cio-alkoxy is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • Ci-C3-Alkoxy is additionally, for example, n-propoxy and 1 - methylethoxy (isopropoxy).
  • Ci-C4-Alkoxy is additionally, for example, butoxy,
  • Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy,
  • 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-C4-haloalkoxy is a Ci-C4-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C6-haloalkoxy is a Ci-C6-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci- Cio-haloalkoxy is a Ci-Cio-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C 2 -Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHC , OCCI3, 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 OC2F5.
  • Ci-C3-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,
  • Ci-C4-Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4- bromobutoxy or nonafluorobutoxy.
  • Ci-C6-Haloalkoxy is additionally, for example, 5- fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
  • Ci-C3-alkoxy-Ci-C3-alkyl refers to a straight-chain or branched alkyl group having 1 to 3 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C3-alkoxy group, as defined above.
  • Ci-C3-alkoxy-Ci-C4-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-C4-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
  • CPF2OCH2 difluoromethoxymethyl
  • CHF2OCH2 trifluoromethoxymethyl
  • 1 -difluoromethoxyethyl 1 -trifluoromethoxyethyl
  • 2-difluoromethoxyethyl 2-trifluoromethoxyethyl
  • difluoro- methoxy-methyl CH3OCF2
  • 1 ,1 -difluoro-2-methoxyethyl 2,2-difluoro-2-methoxyethyl and the like.
  • 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 (isopropylthio).
  • 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,
  • 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.
  • the term "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.
  • C1-C10- 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-trichloroethylthio or SC2F5.
  • chlorofluoromethylthio dichlorofluoromethylthio, chlorodifluoromethylthio,
  • 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,
  • 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.
  • C1-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 -C3-a I kylsu If i nyl is a Ci-C3-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • C 1 -C4-a I ky I s u If i ny I is a C1-C4- alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • C1-C6- alkylsulfinyl is a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-Cio-alkylsulfinyl is a Ci-Cio-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C2-Alkylsulfinyl is methylsulfinyl or ethylsulfinyl.
  • Ci-C4-Alkylsulfinyl is additionally, for example, butylsulfinyl,
  • Ci-C6-Alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1 ,1 - dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 - ethylpropylsulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2-methylpentylsulfinyl,
  • d-Cs-Alkylsulfinyl is additionally, for example, heptylsulfinyl, octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof.
  • C1-C10- Alkylsulfinyl is additionally, for example, nonylsulfinyl, decylsulfinyl and positional isomers thereof.
  • Ci-C2-haloalkylsulfinyl is a Ci-C2-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C3-haloalkylsulfinyl is a C1-C3- haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci- C4-haloalkylsulfinyl is a Ci-C4-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-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- C 2 -Haloalkylsulfinyl is, for example, S(0)CH 2 F, S(0)CHF 2 , S(0)CF 3 , S(0)CH 2 CI, S(0)CHCl2, S(0)CCl3, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl,
  • C1-C3- Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3- fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,
  • C1-C4- Haloalkylsulfinyl is additionally, for example, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl.
  • Ci-C6-Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6- chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or
  • Ci-C2-alkylsulfonyl is a Ci-C2-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, attached via a sulfonyl [S(0)2] group.
  • Ci-C2-Alkylsulfonyl is methylsulfonyl or ethylsulfonyl.
  • 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
  • Ci-C6-Alkylsulfonyl is additionally, 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-C2-haloalkylsulfonyl is a Ci-C2-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,
  • dichlorofluoromethylsulfonyl 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-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl or S(0)2C2F 5 .
  • Ci-C3-Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,
  • C1-C4- 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,
  • undecafluoropentylsulfonyl 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6- bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl.
  • Examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl and the like.
  • Ci-C6-haloalkylcarbonyl a Ci-C6-haloalkylcarbonyl
  • Ci-C4-haloalkylcarbonyl Ci-C4-haloalkylcarbonyl
  • Examples are trifluoromethylcarbonyl, 2,2,2- trifluoroethylcarbonyl and the like.
  • Examples are methoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl and the like.
  • Ci-C6-haloalkoxycarbonyl a Ci-C6-haloalkoxycarbonyl
  • Ci-C4-haloalkoxycarbonyl Ci-C4-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
  • aminocarbonyl is a group -C(0)-NH2.
  • Ci-C6-alkylaminocarbonyl is a group -C(0)-N(H)Ci-C6-alkyl. Examples are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl,
  • di-(Ci-C6-alkyl)aminocarbonyl is a group -C(0)-N(Ci-C6-alkyl)2. Examples are dimethylaminocarbonyl, diethylaminocarbonyl, ethylmethylaminocarbonyl, dipropylaminocarbonyl, diisopropylaminocarbonyl, methylpropylaminocarbonyl, methylisopropylaminocarbonyl, ethylpropylaminocarbonyl,
  • 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, preferably a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heteromonocyclic ring or a 7-, 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- or 6-membered heterocyclic rings are aromatic. Partially unsaturated rings contain less than the maximum number of C-C and/or C-N and/or N-N double bond(s) allowed by the ring size.
  • the heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
  • Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximum unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximum unsaturated 5- or 6-membered heterocyclic rings are aromatic. 7- and
  • 8-membered rings cannot be aromatic. They are homoaromatic (7-membered ring, 3 double bonds) or have 4 double bonds (8-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. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
  • Examples of a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring include:
  • Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-d ihyd rofur-3-yl , 2,4-dihydrofur-2-yl, 2,4-d ihyd rofur-3-yl , 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl,
  • tetrahydropyridinyl 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1 ,3, 5-di- or tetrahydrotriazin-2-yl, 1 ,2, 4-di- or tetrahydrotriazin-3-yl,
  • tetrahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7- tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1 ,3-diazepinyl, tetrahydro- 1 ,4-diazepinyl, tetrahydro-1 ,3-oxazepinyl, tetrahydro-1 ,4-oxazepinyl, tetrahydro-1 ,3- dioxepinyl and tetrahydro-1 ,
  • 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,
  • 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 heteroatom 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
  • 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 (if the latter are not part of a double bond).
  • secondary nitrogen atom i.e. NH
  • the heteromonocyclic ring formed by R 5 and R 6 together with the nitrogen atom to which they are bound mandatorily carries at least one substituent R 7
  • the heterobicyclic ring formed by R 5 and R 6 together with the nitrogen atom to which they are bound optionally carries at least one substituent R 7 .
  • R 5 and R 6 together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, NH, SO, and SO2, as ring members, wherein the
  • heteromonocyclic ring is (mandatorily) substituted with 1 , 2, 3, 4, 5, 6, 7 or 8 substituents R 7 , and where the heterobicyclic ring may be substituted with 1 , 2, 3, 4, 5, 6, 7 or 8 substituents R 7 ; where R 7 has one of the above general or, in particular, one of the below preferred meanings.
  • the heterocyclic ring formed by R 5 and R 6 together with the nitrogen atom to which they are bound is monocyclic.
  • R 5 and R 6 together with the nitrogen atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring, where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, NH, SO, and SO2, as ring members, wherein the heteromonocyclic ring may be (and preferably is) substituted with 1 , 2, 3, 4, 5 or 6 8 substituents R 7 ; where R 7 has one of the above general 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 further contain 1 or 2, preferably 1 , heteroatoms or heteroatom-containing groups selected from O and NH as ring members, wherein the heterocyclic ring may carry (preferably carries) 1 , 2, 3, 4, 5 or 6 substituents R 7 , where R 7 has one of the above general 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
  • heterocyclic ring may further contain 1 or 2 heteroatom-containing groups NH as ring members, wherein the heterocyclic ring may carry (preferably carries) 1 , 2, 3, 4, 5 or 6 substituents R 7 , where R 7 has one of the above general or, in particular, one of the below preferred meanings.
  • Suitable heteromonocyclic rings formed by R 5 and R 6 together with the nitrogen atom they are bound to are for example: aziridin-1 -yl, diaziridin-1 -yl, azetidin-1 -yl, 1 ,2- diazetidin-1 -yl, 1 ,3-diazetidin-1 -yl, pyrrolidin-1 -yl, pyrazolidin-1 -yl, imidazolidin-1 -yl, 1 ,2,3-triazolidin-1 -yl, 1 ,2,3-triazolidin-2-yl, 1 ,2,4-triazolidin-1 -yl, 1 ,2,3-triazolidin-4-yl, piperidin-1 -yl, hexahydropyrimidin-1 -yl, piperazin-1 -yl, azepan-1 -yl, 1 ,4-diazepan-1 -yl, isothiazolid
  • thiomorpholin-4-yl (also termed thiomorpholino), 1-oxothiomorpholin-4-yl, 1 ,1 - dioxothiomorpholin-4-yl, 1 ,4-thiazinan-4-yl, 1 -oxo-1 ,4-thiazinan-4-yl and 1 ,1 -dioxo-1 ,4- thiazinan-4-yl.
  • these heteromonocyclic rings carry 1 , 2, 3, 4, 5, 6, 7 or 8 substituents R 7 . More preferably, these heteromonocyclic rings carry 1 , 2, 3, 4, 5 or 6 substituents R 7 .
  • R 7 has independently of each other one of the above general, 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 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring, where the ring may further contain 1 , 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from O, S, N, NH, SO, and SO2, as ring members, wherein the heterobicyclic ring may be substituted with 1 , 2, 3, 4, 5, 6, 7 or 8 substituents R 7 ; where R 7 has one of the above general or, in particular, one of the below preferred meanings.
  • R 5 and R 6 together with the nitrogen atom to which they are bound, preferably form a 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring, where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, N and NH as ring members, wherein the heterocyclic ring may be substituted with 1 , 2, 3 or 4 substituents R 7 , where R 7 has one of the above general 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 7-, 8-, 9- or 10-membered saturated or partially unsaturated
  • heterobicyclic ring where the ring may further contain 1 or 2 heteroatoms or heteroatom-containing groups selected from O, S, N and NH as ring members, wherein the heterocyclic ring is unsubstituted or substituted with 1 , 2, 3 or 4 substituents R 7 , where R 7 has one of the above general 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 7-, 8-, 9- or 10-membered saturated heterobicyclic ring, where the ring may further contain 1 or 2, preferably 1 , heteroatoms or heteroatom-containing groups selected from O, S, SO, SO2, and NH as ring members, wherein the heterobicyclic ring may be substituted with 1 , 2, 3 or 4, 5 or 6 substituents R 7 , where R 7 has one of the above general or, in particular, one of the below preferred meanings.
  • Suitable heterobicyclic rings formed by N, R 5 and R 6 are for example the following:
  • heterobicyclic rings may carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, substituents R 7 , wherein each R 7 has independently one of the above general, or in particular, one of the below preferred meanings.
  • the radical R 7 can be a substituent on a carbon ring atom as well as on a nitrogen ring atom. In case that it is a substituent on a nitrogen atom, it is not selected from halogen, azido, nitro, -SCN, -SF 5 , -Si(R 12 ) 3 , -OR 9 and -OSO2R 9 , and preferably not from
  • R 7 is selected from cyano, Ci-C6-alkyl, C3-C8- 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 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 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 1 1 ;
  • 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 with 1 , 2, 3, 4 or 5 substituents R 1 1 ; 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 1 1 .
  • each R 7 is independently selected from halogen, cyano, oxo, C1-C6- alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, wherein the 8 last-mentioned
  • the radical R 8 as a substituent on an aliphatic or cycloaliphatic group such as a Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2- C6-haloalkenyl, C2-C6-alkynyl or C2-C6-haloalkynyl group, is preferably selected from cyano; Cs-Cs-cycloalkyl which may be substituted by 1 or 2 substituents selected from CN, methyl, and oxo; Cs-Cs-halocycloalkyl; -OR 9 ; -S(0) n R 9 ; -N(R 0a )R 0b ;
  • R 8 is selected from cyano, C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from CN, methyl and oxo; C3- C6-halocycloalkyl, and -OR 9 .
  • the radical R 8 is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl carrying a CN group; C3-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl-, C3-C8- halocycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the 4 last-mentioned radicals may carry a CN group; C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, -OR 9 and -N(R 10a )R 10 ; wherein R 9 , R 10a , R 10 and R 16 have
  • R 8 is more preferably selected from hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkyl carrying a CN group; Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3- Cs-cycloalkyl-Ci-C4-alkyl, C3-Cs-halocycloalkyl-Ci-C4-alkyl, where the cycloalkyl moieties in the 4 last-mentioned radicals may carry a CN group; C2-C6-alkenyl, C2-C6- haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, -OR 9 and -N(R 10a )R 10 ; wherein R 9 , R 10a , R 10b and R 16 have one of the above general, or in particular, one of the below preferred
  • R 8 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkyl carrying a CN group; Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkyl- Ci-C2-alkyl-, especially C3-Cs-cycloalkyl-CH2-, C3-Cs-halocycloalkyl-Ci-C2-alkyl-, especially C3-Cs-halocycloalkyl-CH2-, where the cycloalkyl moieties in the 6 last- mentioned radicals may carry a CN group; C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C 2 -C 6 -haloalkynyl, -OR 9 and -N(R 10a )R 10b , wherein R 9 , R 10a and
  • R 8 is selected from Ci-C 6 -alkyl, d-Ce-haloalkyl, -OR 9 and -N(R 10a )R 10b , wherein R 9 , R 10a and R 10b have one of the above general, or in particular, one of the below preferred meanings.
  • the radical R 9 is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3- Cs-halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, C3-C8-halocycloalkyl-Ci-C4-alkyl-, C2- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, optionally substituted with 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 comprising 1 , 2 or 3 hetero
  • 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
  • R 9 selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl, and is specifically Ci-C6-alkyl.
  • the radicals R 10a and R 10b are preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl carrying a CN group; C3-C8- cycloalkyi, Cs-Cs-halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl-, Cs-Cs-halocycloalkyl-Ci- C4-alkyl-, where the cycloalkyi moieties in the 4 last-mentioned radicals may carry a CN group;
  • 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 heterocyclic ring is optionally substituted with one or more substituents R 16 ,
  • R 13 , R 14a , R 14b and R 16 have one of the above general, or in particular, one of the preferred meanings.
  • Ci-C6-alkyl Ci-C6-haloalkyl, Ci-C6-alkyl carrying a CN group
  • 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 heterocyclic ring is optionally substituted with one or more substituents R 16 , wherein R 13 , R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, R 16 has one of the above preferred meanings and R 13 , R 14a and R 14b have one of the below preferred meanings.
  • R 10a is hydrogen
  • R 13 , R 14a and R 14b have one of the above general meanings, or, in particular, one of the below preferred meanings
  • R 10a is hydrogen
  • R 10b is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl carrying a CN group; Cs- Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl-, C3-C8- halocycloalkyl-Ci-C4-alkyl-, where the cycloalkyi moieties in the 4 last-mentioned radicals may carry a CN group; C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl.
  • R 10a is hydrogen
  • R 10a is hydrogen or methyl, preferably hydrogen
  • R 13 , R 14a and R 14b have one of the above general meanings, or, in particular, one of the below preferred meanings.
  • R 13 preferably is 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 cycloalkyi moieties in the three last-mentioned groups may be substituted by a cyano group; Ci-C6-alkyl substituted with a CN group, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 13 is 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 cycloalkyi moieties in the three last-mentioned groups may be substituted by a cyano group; and Ci-C6-alkyl substituted with a CN group.
  • R 10a and R 10b in the above mentioned radical R 10a and R 10b
  • R 13 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, where the cycloalkyi moieties in the two last-mentioned groups may be substituted by a cyano group; Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 10a and R 10b are examples of the above radicals.
  • R 14a is preferably selected from hydrogen and Ci-C6-alkyl
  • 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 cycloalkyi moieties in the three last-mentioned groups may be substituted by a cyano group; and C1-C6- alkyl substituted with a CN group.
  • R 10a and R 1 R 14a is preferably selected from hydrogen and Ci-C6-alkyl
  • R 14b is preferably selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl.
  • R 8 , R 10 and R 10 have one of the above general meanings, or, in particular, have one of the above preferred meanings.
  • R 8 is hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl carrying a CN group; Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, C3-C8-cycloalkyl-Ci-C2-alkyl-, C3-C8- halocycloalkyl-Ci-C2-alkyl-, where the cycloalkyl moieties in the 4 last-mentioned radicals may carry a CN group; C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C 2 -C 6 -haloalkynyl, -OR 9 and -N(R 10a )R 10 , where R 9 , R 10a and R 10 have one of the preferred meanings;
  • R 13 is 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 groups may be substituted by a cyano group; Ci-C6-alkyl substituted with a CN group, Ci-C4-alkoxy and Ci-C4-haloalkoxy; and
  • R 10b is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl carrying a CN group; Cs- Cs-cycloalkyl, C3-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl-, C3-C8- halocycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moieties in the 4 last-mentioned radicals may carry a CN group; C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl.
  • R 8 is hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl carrying a CN group; C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8-cycloalkyl-Ci-C 2 -alkyl-, C3-C8- halocycloalkyl-Ci-C 2 -alkyl-, where the cycloalkyl moieties in the 4 last-mentioned radicals may carry a CN group; C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C 6 -haloalkynyl, -OR 9 and -N(R 10a )R 10b , where R 9 , R 10a and R 10b have one of the preferred meanings;
  • R 13 is hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 -C6- alkynyl, C 2 -C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6- cycloalkyl-Ci-C 4 -alkyl-, where the cycloalkyl moieties in the three last-mentioned groups may be substituted by a cyano group; and Ci-C6-alkyl substituted with a CN group and
  • R 10b is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl carrying a CN group; C3- Cs-cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 8 -cycloalkyl-Ci-C 4 -alkyl-, C 3 -C 8 - halocycloalkyl-Ci-C 4 -alkyl-, where the cycloalkyl moieties in the 4 last-mentioned radicals may carry a CN group; C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl and C 2 -C6-haloalkynyl.
  • R 7 is selected from fluorine, cyano, oxo, methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, CF 3 , CH 2 CHF 2 , CH 2 CHF 2 , CH 2 CF 3 ,
  • R 8 is d-Ce-alkyl, Ci-C 6 -haloalkyl, or -OR 9 and -N(R 10a )R 10 , where R 9 has one of the above preferred meanings and is in particular Ci-C6-alkyl or Ci-C6-haloalkyl;
  • R 13 is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, where the cycloalkyl moieties in the two last-mentioned groups may be substituted by a cyano group; Ci-C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy;
  • R 10b is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl carrying a CN group; C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C 4 -alkyl-, C3-C8- halocycloalkyl-Ci-C 4 -alkyl-, where the cycloalkyl moieties in the 4 last-mentioned radicals may carry a CN group; C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl and C 2 -C6-haloalkynyl;
  • R 14a is selected from hydrogen and Ci-C6-alkyl
  • R 14b is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl.
  • W is O.
  • B 1 , B 2 and B 3 are CR 2 . More preferably, B 1 and B 3 are CR 2 , where R 2 is not hydrogen, and B 2 is CR 2 , where R 2 has one of the meanings given above.
  • 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 -NR 10a R 10b , wherein n, R 8 , R 9 , R 10a and R 10b have one of the above general meanings, or, in particular, one of the below preferred meanings. More preferably, R 2 is selected from hydrogen, halogen and Ci-C2-haloalkyl, preferably from hydrogen, F, CI, Br and CF3.
  • B 1 and B 3 are C-CI and B 2 is C-F. In a further particular embodiment, B 1 and B 3 are C-CF3 and B 2 is C-H. In a further particular embodiment B 1 and B 3 are C-Br and B 2 is C-F. In a further particular embodiment, B 1 , B 2 and B 3 are C- Cl. In a further particular embodiment, B 1 is C-CI, B 2 is C-H and B 3 is C-CF3. In a further particular embodiment, B 1 is C-Br, B 2 is C-H and B 3 is C-CF3. Specifically, B 1 and B 3 are C-CI and B 2 is C-F.
  • G 1 , G 2 , G 3 and G 4 are CR 4 , where R 4 has one of the meanings given above or below.
  • G 1 , G 3 and G 4 are CR 4 and G 2 is N, where R 4 has one of the meanings given above or below.
  • G 2 , G 3 and G 4 are CR 4 and G 1 is N, where R 4 has one of the meanings given above or below.
  • G 1 , G 3 and G 4 are CH and G 2 is CR 4 , where R 4 has one of the above general or, in particular, one of the below preferred meanings.
  • R 4 is selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkylthio; and preferably from hydrogen, halogen and methyl.
  • R 1 is Ci-C4-haloalkyl, specifically Ci-C2-haloalkyl or
  • R 15 is Ci-C4-alkyl. More specifically R 1 is halomethyl, in particular fluoromethyl, such as fluoromethyl, difluoromethyl and trifluoromethyl, and is very specifically trifluoromethyl.
  • R 3a and R 3b are selected, independently of each other, from hydrogen, halogen, hydroxyl, Ci-C3-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, Ci-C3-haloalkyl, C1-C3- alkoxy, Ci-C3-alkylthio and Ci-C3-alkylsulfonyl. More preferably, R 3a and R 3b are selected, independently of each other, from hydrogen and halogen, preferably hydrogen and fluorine and are in particular hydrogen.
  • R 8 , R 9 , R 10a , R 10b , R 11 , R 12 , R 13 , 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
  • 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 heteroatoms 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- 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, C3-C6-halocycloalkylaminocarbonyl, and a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or hetero
  • 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 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 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 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-C4- 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, C3-C8- halocycloalkyl, -OH, -SH, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -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-alky
  • 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, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy 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 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, Ci- 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, Ci- 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 unsubstituted and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
  • compound I is a compound of formula IA, i.e.
  • B 1 is CR 2a
  • B 2 is CR 2b
  • B 3 is CR 2c
  • R 1 is CF 3
  • R 3a and R 3b are each hydrogen
  • G 1 is C-H
  • G 3 is C-H
  • G 4 is C-H
  • G 2 is C-R 4 ,
  • R 4 , R 5 and R 6 have one of the above-given general or, in particular, one of the above-given preferred meanings
  • R 2a , R 2b and R 2c independently of each other, have one of the general or, in particular, one of the preferred meanings given above for R 2 , except for compounds IA wherein R 2a and R 2c are CI, and simultaneously R 2b is H, R 4 is F, CI, CH3 or SCH3, and R 5 and R 6 , together with the nitrogen atom they are bound to, form a ring selected from unsubstituted aziridin-1 -yl, unsubstituted azetidin-1 - yl, unsubstituted pyrrolidin-1 -yl, unsubstituted piperidin-1 -yl, unsubstituted thiazolidin-3- yl, unsubstituted morpholin-4-yl, unsubstituted thiomorpholin-4-yl,
  • Examples of preferred compounds are compounds of the following formulae la.1 to la.52, 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 265 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 2a , R 2b , R 2c and R 4 for a compound corresponds in each case to one row of Table A.
  • Tables 62 to 71 Compounds of the formula la.35 in which R 7a is as defined in any of tables 32 to 41 and the combination of R 2a , R 2b , R 2c and R 4 for a compound corresponds in each case to one row of Table A.
  • Tables 152 to 161 Compounds of the formula la.44 in which R 10b is as defined for R 7a in any of tables 32 to 41 and the combination of R 2a , R 2b , R 2c and R 4 for a compound corresponds in each case to one row of Table A.
  • Tables 226 to 235 Compounds of the formula la.49 in which R 8 is as defined for R 7a in any of tables 32 to 41 and the combination of R 2a , R 2b , R 2c and R 4 for a compound corresponds in each case to one row of Table A.
  • the compounds of the formula I can be prepared by the methods as described in the below schemes or synthesis descriptions or in the synthesis descriptions of the working examples or by standard methods of organic chemistry.
  • the substituents, variables and indices are as defined above for formula I, if not otherwise specified.
  • A is A or a precursor of A, wherein A is a group
  • Typical precursors of A are a halogen atom, CN, carboxy, tert-butoxycarbonyl, an acetale group, a protected aldehyde group or -OS02-R z1 , where R z1 is Ci-C4-alkyl, Ci-C4-haloalkyl or phenyl which may be substituted by 1 , 2 or 3 radicals selected from Ci-C4-alkyl, Ci-C4-haloalkyl Ci- C 4 -alkoxy or Ci-C 4 -haloalkoxy.
  • Compounds ⁇ correspond to compounds I when A' is A.
  • Dehydration either occurs spontaneously or with the help of dehydrating agents, such as molecular sieves, acid-washed molecular sieves, magnesium sulfate, sodium sulfate, silica gel, SOC , POC , Burgess reagent, trifluoroacetic anhydride, p-toluene sulfonic acid, anhydrous HCI or sulfuric acid.
  • dehydrating agents such as molecular sieves, acid-washed molecular sieves, magnesium sulfate, sodium sulfate, silica gel, SOC , POC , Burgess reagent, trifluoroacetic anhydride, p-toluene sulfonic acid, anhydrous HCI or sulfuric acid.
  • p-toluene sulfonic acid or acid- washed molecular sieves are used.
  • the water formed may alternatively be removed, e.g. by
  • Compounds 1 wherein R 3b is hydrogen can be prepared by reacting a compound 3 with an amination agent to give a compound of formula 2, which reacts spontaneously to the compound 1 , as shown in scheme 2.
  • amination can the carried out in a one step reaction, wherein compound 3 reacts directly to compound 2, or as a two step reaction, wherein the SH group of compound 3 is first oxidized to a S-CI group, which then further reacts to a S-NH2 group, thus giving compound 2.
  • Suitable amination agents for the one step reaction are for example HOSA
  • hydroxylamine-O-sulfonic acid which is generally used in the presence of a base
  • suitable bases being for example sodium hydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methanolate, triethylamine and the like
  • O- (diphenylphosphoryl)hydroxyl amine which is generally also used in the presence of a base
  • suitable bases being for example sodium hydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium methanolate, triethylamine and the like
  • 2,4- dinitrophenylhydroxyl amine O-mesitylensulfonylhydroxylamine and 2-oxa-1 - azaspiro[2.5]octane, among which HOSA and 0-(diphenylphosphoryl)hydroxyl amine are preferred.
  • the amination is generally carried out in a solvent, suitable solvents being for example chlorinated alkanes, such as methylene chloride or chloroform, aromatic solvents, such as benzene, toluene, the xylenes, chlorobenzene or dichlorobenzene, and ethers, such as diethylether, dipropylether, methyl tert-butylether, methyl isobutylether, ethylenegylcol dimethylether, tetrahydrofuran (THF) or dioxane and the like.
  • the reaction is suitably carried out low temperature, e.g. at from -100 to 0°C or -78 to 0°C.
  • the compound 3 is dispersed in a solvent and cooled to the desired temperature and the base is added followed by the amination agent, or the amination agent is added followed by the base, or base and amination agent are added simultaneously.
  • HOSA is suitably used in combination with an amine base, such as triethylamine. In this case, it is preferred to cool compound 3 to -30 to 0°C, preferably - 20 to -10°C, to add the amine base at this temperature and then HOSA and keep the reaction at approximately -10 to 0°C.
  • 0-(diphenylphosphoryl)hydroxyl amine can be used in combination with a base, e.g. with an inorganic base, such as sodium hydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate and specifically sodium hydrogen phosphate.
  • a base e.g. with an inorganic base, such as sodium hydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate and specifically sodium hydrogen phosphate.
  • a base e.g. with an inorganic base, such as sodium hydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate and specifically sodium hydrogen phosphate.
  • a base e.g. with an inorganic base, such as sodium hydrogen phosphate, potassium hydrogen phosphate, sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate and specifically sodium hydrogen phosphate.
  • it is suitable to cool compound 3 to
  • the compound 3 is first reacted with a chlorination agent which converts the SH group into an S-CI group.
  • Suitable chlorination agents are for example sulfurylchloride, N-chloro succinimide (NCS), sodium hypochlorite, monochloroamine (NH2CI) or chlorine, which is preferably used in the presence of FeC .
  • the chlorination can be carried out in analogy to the method described in Synthesis 1987, 1987, 683- 688, Tetrahedron 66(36), 2010, 7279-7287, J. Org. Chem. 59(4), 1994, 914-921 , J. Org. Chem. 63, 1998, 4878-4888 or J. Chem Soc. 1938, 21 14-21 17.
  • the chlorination is generally carried out in a solvent.
  • Suitable solvents are for example ethers, such as diethylether, dipropylether, methyl tert-butylether, methyl isobutylether, ethylenegylcol dimethylether, tetrahydrofuran or dioxane.
  • the reaction temperature can vary over wide ranges and is generally from 0°C to the boiling point of the reaction mixture (if a solvent is used).
  • the chlorinated compound is then reacted without isolation with ammonia or ammonium hydroxide. If anhydrous ammonia is used, the reaction is generally carried out at from -78 to -33°C.
  • the reaction can also be carried out at higher temperatures, such as 0 to 25°C.
  • the reaction is generally carried out in a solvent. Suitable solvents are for example the above-listed ethers, among which the water-miscible ethers, such as THF and dioxane, are preferred.
  • the chlorinated compound is dissolved in a solvent to which ammonia or ammonium hydroxide is added.
  • the reaction can be carried out as described, for example, in Synthesis, 1987, 8, 683-688.
  • chlorination/amination can also be carried as a one pot reaction.
  • the thiol 3 is reacted simultaneously with a chlorinating agent (such as NCS or aqueous sodium hypochlorite) and anhydrous or aqueous ammonia in ethereal solvents (such as THF or Et 2 0) or water.
  • a chlorinating agent such as NCS or aqueous sodium hypochlorite
  • anhydrous or aqueous ammonia in ethereal solvents such as THF or Et 2 0
  • ethereal solvents such as THF or Et 2 0
  • the reaction with NCS in a mixture of THF and anhydrous liquid ammonia at -33°C for instance, a solution of the thiol 3 in THF is added to a solution of NCS (N-chlorosuccinimide) in THF/liquid ammonia at -78°C. The solution is warmed to -30°C and stirred until the ammonia
  • chlorination/amination reaction can be carried out as described, for example, in Tetrahedron 2010, 66, 7279-7287 or in J. Org. Chem. 1994, 59, 914-921 .
  • Compound 2 can virtually not be isolated as it generally reacts spontaneously in a ring- closing reaction to compound 1.

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9420793B2 (en) 2015-01-16 2016-08-23 Avista Pharma Solutions Antiparasitic compounds
WO2018166855A1 (en) 2017-03-16 2018-09-20 Basf Se Heterobicyclic substituted dihydroisoxazoles
US10266708B2 (en) 2015-09-16 2019-04-23 Apeel Technology, Inc. Precursor compounds for molecular coatings
US10517310B2 (en) 2015-05-20 2019-12-31 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
US10537115B2 (en) 2016-01-26 2020-01-21 Apeel Technology, Inc. Method for preparing and preserving sanitized products
US10537130B2 (en) 2013-07-29 2020-01-21 Apeel Technology, Inc. Agricultural skin grafting
US10561155B2 (en) 2015-12-10 2020-02-18 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
US10807992B2 (en) 2017-11-16 2020-10-20 Avista Pharma Solutions, Inc. Single enantiomer antiparasitic compounds
US10843997B2 (en) 2016-11-17 2020-11-24 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof
US11576382B2 (en) 2018-02-12 2023-02-14 Fmc Corporation Naphthalene isoxazoline compounds for controlling invertebrate pests
US11641865B2 (en) 2020-03-04 2023-05-09 Apeel Technology, Inc. Compounds and formulations for protective coatings
US11827591B2 (en) 2020-10-30 2023-11-28 Apeel Technology, Inc. Compositions and methods of preparation thereof
US12245605B2 (en) 2018-09-05 2025-03-11 Apeel Technology, Inc. Compounds and formulations for protective coatings
US12408680B2 (en) 2021-09-08 2025-09-09 Apeel Technology, Inc. Compounds and formulations for protective coatings

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1731512A1 (en) * 2004-03-05 2006-12-13 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and noxious organism control agent
WO2011092287A1 (en) * 2010-02-01 2011-08-04 Basf Se Substituted ketonic isoxazoline compounds and derivatives for combating animal pests
WO2013037626A1 (en) * 2011-09-13 2013-03-21 Syngenta Participations Ag Isothiazoline derivatives as insecticidal compounds
WO2013092943A1 (en) * 2011-12-23 2013-06-27 Basf Se Isothiazoline compounds for combating invertebrate pests

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1731512A1 (en) * 2004-03-05 2006-12-13 Nissan Chemical Industries, Ltd. Isoxazoline-substituted benzamide compound and noxious organism control agent
WO2011092287A1 (en) * 2010-02-01 2011-08-04 Basf Se Substituted ketonic isoxazoline compounds and derivatives for combating animal pests
WO2013037626A1 (en) * 2011-09-13 2013-03-21 Syngenta Participations Ag Isothiazoline derivatives as insecticidal compounds
WO2013092943A1 (en) * 2011-12-23 2013-06-27 Basf Se Isothiazoline compounds for combating invertebrate pests

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10537130B2 (en) 2013-07-29 2020-01-21 Apeel Technology, Inc. Agricultural skin grafting
US9686991B2 (en) 2015-01-16 2017-06-27 Avista Pharma Solutions, Inc. Antiparasitic compounds
US9883674B2 (en) 2015-01-16 2018-02-06 Avista Pharma Solutions, Inc. Antiparasitic compounds
US9420793B2 (en) 2015-01-16 2016-08-23 Avista Pharma Solutions Antiparasitic compounds
US10092001B2 (en) 2015-01-16 2018-10-09 Avista Pharma Solutions, Inc. Antiparasitic compounds
US10772331B2 (en) 2015-01-16 2020-09-15 Avista Pharma Solutions, Inc. Antiparasitic compounds
US10342234B2 (en) 2015-01-16 2019-07-09 Avista Pharma Solutions, Inc. Antiparasitic compounds
US10959442B2 (en) 2015-05-20 2021-03-30 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
US11160287B2 (en) 2015-05-20 2021-11-02 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
US10517310B2 (en) 2015-05-20 2019-12-31 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
US11812758B2 (en) 2015-05-20 2023-11-14 Apeel Technology, Inc. Plant extract compositions and methods of preparation thereof
US12173192B2 (en) 2015-09-16 2024-12-24 Apeel Technology, Inc. Precursor compounds for molecular coatings
US10266708B2 (en) 2015-09-16 2019-04-23 Apeel Technology, Inc. Precursor compounds for molecular coatings
US11472970B2 (en) 2015-09-16 2022-10-18 Apeel Technology, Inc. Precursor compounds for molecular coatings
US11447646B2 (en) 2015-09-16 2022-09-20 Apeel Technology, Inc. Precursor compounds for molecular coatings
US11767278B2 (en) 2015-12-10 2023-09-26 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
US10561155B2 (en) 2015-12-10 2020-02-18 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
US11028030B2 (en) 2015-12-10 2021-06-08 Apeel Technology, Inc. Plant extract compositions for forming protective coatings
US11723377B2 (en) 2016-01-26 2023-08-15 Apeel Technology, Inc. Method for preparing and preserving sanitized products
US10537115B2 (en) 2016-01-26 2020-01-21 Apeel Technology, Inc. Method for preparing and preserving sanitized products
US10843997B2 (en) 2016-11-17 2020-11-24 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof
US11918003B2 (en) 2016-11-17 2024-03-05 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof
US11319275B2 (en) 2016-11-17 2022-05-03 Apeel Technology, Inc. Compositions formed from plant extracts and methods of preparation thereof
WO2018166855A1 (en) 2017-03-16 2018-09-20 Basf Se Heterobicyclic substituted dihydroisoxazoles
US10807992B2 (en) 2017-11-16 2020-10-20 Avista Pharma Solutions, Inc. Single enantiomer antiparasitic compounds
US11576382B2 (en) 2018-02-12 2023-02-14 Fmc Corporation Naphthalene isoxazoline compounds for controlling invertebrate pests
US12137688B2 (en) 2018-02-12 2024-11-12 Fmc Corporation Naphthalene isoxazoline compounds for controlling invertebrate pests
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JP2016527208A (ja) 2016-09-08
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