WO2012085081A1 - Composés sulfoximinamides servant à lutter contre des animaux nuisibles invertébrés ii - Google Patents

Composés sulfoximinamides servant à lutter contre des animaux nuisibles invertébrés ii Download PDF

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WO2012085081A1
WO2012085081A1 PCT/EP2011/073586 EP2011073586W WO2012085081A1 WO 2012085081 A1 WO2012085081 A1 WO 2012085081A1 EP 2011073586 W EP2011073586 W EP 2011073586W WO 2012085081 A1 WO2012085081 A1 WO 2012085081A1
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alkyl
compounds
het
hydrogen
radicals
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Ralph Paulini
Wolfgang Von Deyn
Henricus Maria Martinus Bastiaans
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/88—Nitrogen atoms, e.g. allantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/22—Nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/14—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 three or more hetero rings

Definitions

  • the present invention relates to novel sulfoximinamid compounds, to their enanti- omers, their diastereomers and their salts which are useful for combating or controlling invertebrate pests, in particular insects, arthropod pests and nematodes.
  • the invention further relates to methods for controlling invertebrate pests by using these compounds.
  • the invention further relates to methods for treating animals and for protecting seeds and/or growing plants by using these compounds.
  • the present invention further relates to seeds and to agricultural and/or veterinary compositions comprising said compounds.
  • Herbicidal sulfonimidamide compounds have been described in EP173498.
  • Other general sulfoximine compounds such as arylsulfoximine compounds have been described as herbicide and pesticide in GB 1307271 .
  • Pyrazole, pyrrole und imidazole derivatives of sulfoximine compounds and their pesticidal activity can be found in WO 9639389.
  • Isoxazoline derivatives of sulfoximine compounds and their herbicidal activity have been discussed in WO 2006037945. Insecticidal activities of alkyl-substituted sulfoximine compounds can be found in WO 2006060029.
  • Invertebrate pests and in particular insects, arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, thereby 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 ongoing need for new agents for combating invertebrate pests such as insects, arachnids and nematodes. It is therefore an object of the present invention to provide compounds having a good pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control insects, arachnids and nematodes.
  • the present invention relates to sulfoximinamide compounds of formula I, wherein A is OR 5 , SR 6 , N R 7 R 8 or CR 9a R 9b R 9c ; B is O, S, or N R 10 ; n is 0, 1 or 2;
  • R 1 , R 2 are selected independently from one another from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, d-Ce-alkoxy, Ci-C 6 -alkylthio, CN , N0 2 , C(0)R c , C(0)OR a , C(0)N R a R b ,
  • alkyl, cycloalkyi, alkenyl, alkynyl, alkoxy and alkylthio radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d ; or
  • R 1 and R 2 together with the carbon atom, which they attached to, form a 3- to 6- membered saturated carbocycle, wherein each of the carbon atoms of said car- bocycle are unsubstituted or may carry any combination of 1 or 2 radicals Ra;
  • R 3 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C(0)R c , C(0)OR a ,
  • alkyl, cycloalkyi, alkenyl, alkynyl and alkoxy radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d ;
  • R 4 is selected from Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or N R e R f ,
  • alkyl, cycloalkyi, alkenyl and alkynyl radicals are un- substituted, partly or completely halogenated or may carry any combination of 1 ,
  • R 3 and R 4 together with the nitrogen and sulfur atoms to which they are bound form a saturated or unsaturated 4-, 5- or 6-membered heterocyclic ring, which may contain one additional heteroatom selected from N , O and S, whereas the carbon at- oms of the heterocyclic ring are unsubstituted or each may carry any combination of 1 or 2 radicals Ra and whereas the additional N-atom, if present, carries a radical R h ;
  • R 5 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6- alkenyl, C 2 -C 6 -alkynyl, C(0)R c , C(S)R C , C(0)OR a , C(0)NR a R b , C(S)NR a R b , NR e R f , where the aforementioned alkyl, cycloalkyl, alkenyl and alkynyl radical
  • R 6 has one of the meanings given for R 5 ;
  • R 7 is selected from the group consisting of hydrogen, OH, NR a R b , cyano, nitro, Ci- Ce-alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 -alkoxy, C(0)R c , C(S)R C , C(0)OR a , C(0)NR a R b , or C(S)NR a R b , S(0) m R c , S(0) m NR a R b ,
  • alkyl, cycloalkyl, alkenyl, alkynyl and alkoxy radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d ;
  • R 8 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl and Ci-C6-alkoxy,
  • alkyl, cycloalkyl, alkenyl, alkynyl and alkoxy radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d ; or
  • R 7 and R 8 together with the nitrogen atom they are attached to, form a saturated or unsaturated, N-bound, 5-, 6- or 7-membered heterocyclic ring, optionally containing an additional heteroatom selected from N, O and S, whereas each of the carbon atoms of the heterocyclic ring may optionally carry any combination of 1 or 2 radicals Ra and whereas the additional N-atom, if present, carries a radical R h ;
  • R 9a , R 9b are selected independently of each other from the group consisting of hydrogen, halogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci- Ce-alkoxy, CN, C(0)R c , C(0)OR a , C(0)NR a R b , C(S)NR a R or S(0) m R c , wherein the aforementioned alkyl, cycloalkyl, alken
  • R 9a and R 9b together with the carbon atom to which they are bound are linked to form a 4-, 5-, 6- or 7-membered heterocyclic ring, optionally containing an additional heteroatom selected from N, O, S, whereas each of the carbon atoms of the heterocyclic ring may optionally carry any combination of 1 or 2 radicals Ra and whereas the additional N-atom, if present, carries a radical R h ;
  • R 9c has one of the meanings given for R 9 or is N0 2 , C(S)N R a R or S(0) m R c ;
  • R 10 is selected from the group consisting of hydrogen, OH, NR a R b , cyano, nitro, Ci- Ce-alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 -alkoxy, C(0)R c , C(S)R C , C(0)OR a , C(0)NR a R b , or C(S)NR a R b , S(0) m R c , S(0) m NR a R b , wherein the aforementioned alkyl, cycloalkyl, alkenyl, alkynyl and alkoxy radicals are unsub- stituted, partly or completely halogenated or may carry any combination of
  • phenyl, heteroaryl, phenyl-Ci-C4-alkyl and heteroaryl-Ci-C4-alkyl wherein the rings of the four last mentioned radicals are unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents, which, independently from each other are selected from the group consisting of halogen, nitro, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy; or
  • R 10 and one of R 5 , R 6 , R 7 or R 8 together form a linear C 2 -C 4 -alkandiyl or C 2 -C 4 - alkendiyl moiety
  • C 2 -C4-alkandiyl or C 2 -C4-alkendiyl may be replaced by a heteroatom selected from O, S, N and N-R h , or by a carbonyl or thiocarbonyl group,
  • each of the carbon atoms of C 2 -C4-alkandiyl and C 2 -C4-alkendiyl are unsubstituted or may each carry any combination of 1 or 2 radicals Ra;
  • Het is a 5- or 6-membered C-bound or N-bound, saturated, unsaturated or aromatic heterocycle, having at least one heteroatom group, selected from O, S, N and N-
  • X is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloal- kyl, C3-C6 cycloalkyl, C 2 -C6 alkenyl, C 2 -C6 haloalkenyl, C 2 -C6 alkynyl, C 2 -C6 haloalkynyl, C(0)R c , C(0)OR a , C(0)NR a R b , C(S)NR a R and S(0) m R c , wherein
  • Y is selected from the group consisting of halogen, C1-C6 alkyl, C3-C6 cycloalkyl, C 2 -C6 alkenyl, C 2 -C6 alkynyl, C1-C6 alkoxy, C 2 -C6-alkenyloxy, C 2 -C6- alkynyloxy, Ci-C 4 -alkylthio, CN, N0 2 , S(0) m R c , C(0)R c , C(0)OR a , C(0)NR a R b and C(S)NR a R , wherein
  • alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, al- kenyloxy and alkynyloxy radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d ; and wherein
  • R a , R b are selected independently from one another from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6- haloalkenyl and C3-C6-alkynyl;
  • R c is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6- cycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl and C2-C6-alkynyl;
  • R d is selected from the group consisting of Ci-C4-alkyl, C3-C6-cycloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C4- alkylthio, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, wherein all carbon atoms of the aforementioned 10 radicals are unsubstituted or may be partially of fully halogenated,
  • rings of the four last mentioned radicals may carry 1 , 2, 3, 4 or 5 sub- stituents, which, independently from each other are selected from halogen, nitro, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
  • R e , R f , R h are selected independently from one another from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6- haloalkenyl, C 3 -C 6 -alkynyl, C(0)R c , C(0)OR a , C(0)NR a R b and C(S)NR a R ; or
  • R e , R f together with the nitrogen atom they are attached to, form a saturated or unsaturated, N-bound, 5-, 6- or 7-membered heterocyclic ring, optionally containing an additional heteroatom selected from N , O and S, whereas each of the car- bon atoms of the heterocyclic ring may optionally carry any combination of 1 or 2 radicals Ra and whereas the additional N-atom, if present, carries a radical R h ;
  • R9, R are selected independently from one another from the group consisting of halogen and the meanings given for R d ;
  • n 0, 1 or 2, or the salts thereof, the enantiomers thereof and the diastereomers thereof.
  • a further aspect of the present invention relates to compounds of the formula II
  • the compounds of the present invention i.e. the compounds of formulae I and II, their salts, their enantiomers and their diastereomers, are particularly useful for controlling invertebrate pests, in particular for controlling arthropods and nematodes, especially for controlling insects, in particular for controlling insects of the order Hemiptera and Thy- sanoptera.
  • the invention also relates to the use of a compound of the present invention, for controlling invertebrate pests, in particular for controlling arthropods and nematodes, especially for controlling insects, in particular for controlling insects of the order Hemiptera and Thysanoptera.
  • a further aspect of the present invention relates to 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, plants, seeds, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of the present invention.
  • a further aspect of the present invention relates to a method for protecting plant propagation material, in particular seed and/or the plants which grow therefrom, which method comprises treating the plant propagation material with a pesticidally effective amount of a compound of the present invention.
  • a further aspect of the present invention relates to plant propagation material, in particular seeds, comprising at least one compound of the present invention.
  • a further aspect of the present invention relates to a compound of the present invention for the use in a method for treating or protecting a human or in particular a non-human animal from infestation or infection by parasites especially ectoparasites.
  • a further aspect of the present invention relates to a method for treating or protecting an animal, in particular a non-human animal, from infestation or infection by parasites especially ectoparasites which comprises bringing the animal in contact with a parasiti- cidally effective amount of a compound of the present invention or with a veterinary composition containing a compound of the invention and optionally means for applying or administering it to the animal.
  • a further aspect of the present invention relates to a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of the present invention.
  • a further aspect of the present invention relates to an agricultural or veterinary composition containing at least one compound of the present invention and at least one liquid or solid carrier.
  • the compounds of the present invention may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the pure enantiomers or pure diastereomers of the formulae I or I I and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compounds I or I I or their mixtures.
  • Suitable compounds of the formulae I or I I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
  • the compounds of the formulae I and I I may be present in the form of their tautomers.
  • the invention also relates to the tautom- ers of the formulae I and I I and the salts of said tautomers.
  • R 3 is hydrogen
  • the compounds I and I I may be present in tautomeric forms I-TIA or I-TI B and I I-TIA or I I-T1 B, respectively.
  • the compounds I and I I may be present in tautomeric forms I-T2A, I-T2B or I-T3C and I I-T2A, I I-T2B or I I-T3C, respectively.
  • the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of formula I, their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula I, its enantiomers or diastereomers, as well as amor- phous or crystalline salts thereof.
  • Salts of the compounds of the present invention are preferably agriculturally and veterinary acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic func- tionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
  • 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 pesticidal 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, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, di- methylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammo- nium and benzl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4- alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen- sulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phos- phoric acid or nitric acid.
  • Veterinarily acceptable salts of the compounds of formulae I or II encompass especially the acid addition salts which are known and accepted in the art for the formation of salts for veterinary use.
  • Suitable acid addition salts e.g. formed by compounds of for- mulae I or II 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, e.g. the monoacid salts or diacid salts of maleic acid, dimaleic acid, fumaric acid, e.g. the monoacid salts or diacid salts of fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
  • inorganic acids for example hydrochlorids, sulphates, phosphates, and
  • invertebrate pest encompasses animal populations, such as arthropode pests, including insects and arachnids, as well as 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.
  • arthropode pests including insects and arachnids, as well as 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 includes 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. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • 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.
  • cultiva plants as used herein includes plants which have been modified by breeding, mutagenesis or genetic engineering.
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s) (oligo- or polypeptides) poly for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties (e.g. as disclosed in Biotechnol Prog. 2001 Jul- Aug;17(4):720-8., Protein Eng Des Sel. 2004 Jan;17(1 ):57-66, Nat. Protoc.
  • cultiva plants as used herein further includes plants that have been rendered tolerant to applications of specific classes of herbicides, such as hy- droxy-phenylpyruvate dioxygenase (H PPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e. g. US 6,222,100, WO 01/82685, WO
  • H PPD hy- droxy-phenylpyruvate dioxygenase
  • ALS acetolactate synthase
  • EP-A-0242236, EP-A-242246) or oxynil herbicides see e. g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering.
  • mutagenesis for example Clearfield ® summer rape (Canola) being tolerant to imidazolinones, e. g. imazamox.
  • cultiva plants as used herein further includes plants 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 delta-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, for example Photorhabdus spp.
  • delta-endotoxins e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c
  • VIP vegetative insecticid
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine prote- ase inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium or calcium
  • 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, for example WO 02/015701 ).
  • Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are dis-closed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073.
  • cultivars as used herein further includes plants 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, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora in- festans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes for example potato cultivars, which express resistance genes acting against Phytophthora in- festans derived from the mexican wild potato Solanum bulbocastanum
  • T4-lysozym e. g. potato cultivar
  • cultivadas plants as used herein further includes plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to in- crease the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting envi- ron-mental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
  • cultivadas plants as used herein further includes plants 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, for ex-ample oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape).
  • cultiva plants as used herein further includes plants 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, for example potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato).
  • 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, alkylcarbonyl, alkyl- thio, alkylsulfinyl, alkylsulfonyl and alkoxyalkyi denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms.
  • Examples of an alkyl group are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl,
  • 3-methylhexyl 4-methylhexyl, 5-methylhexyl, 1 -ethyl pentyl, 2-ethylpentyl, 3-ethylpentyl, 1 -propylpentyl, n-octyl, 1 -methyloctyl, 2-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl, 1 -propylpentyl and 2-propylpentyl.
  • alkylene (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.
  • haloalkyl as used herein and in the haloalkyl moieties of haloalkoxy, haloal- kylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl, denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, fre- quently from 1 to 6 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms.
  • Preferred haloalkyl moieties are selected from Ci-C4-haloalkyl, more preferably from Ci-C2-haloalkyl, in particular from
  • Ci-C2-fluoroalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like.
  • alkoxy denotes in each case a straight-chain or branched alkyl group usually having from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, which is bound to the remainder of the molecule via an oxygen atom.
  • alkoxy group examples are methoxy, ethoxy, n-propoxy, iso- propoxy, n-butyloxy, 2-butyloxy, iso-butyloxy, tert-butyloxy, and the like.
  • haloalkoxy denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 10 carbon atoms, frequently from 1 to 4 carbon atoms, preferably 1 to 3 carbon atoms, wherein the hydro- gen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms.
  • Preferred haloalkoxy moieties include Ci-C4-haloalkoxy, in particular Ci-C2-fluoroalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,
  • cycloalkyl as used herein and in the cycloalkyl moieties of cycloalkoxy and cycloalkylalkyl denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms or 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.1 .1]hexyl, bicy- clo[3.1 .1 ]heptyl, bicyclo[2.2.1 ]heptyl, and bicyclo[2.2.2]octyl.
  • Cs-Cio-cycloalkenyl as used herein and in the Cs-Cio-cycloalkenyl moieties of C5-Cio-cycloalkenyl-Ci-C5-alkyl denotes in each case an aliphatic ring system radical having 5 to 10 carbons that comprises at least one carbon-carbon double bond in the ring.
  • Examples of cycloalkenyl groups include, but are not limited to, cyclopropenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like.
  • C n -Cm-cycloalkyl-C 0 -Cp-alkyl refers to a cycloalkyl group, as defined above, having n to m carbon atoms, which is bound to the remainder of the molecule via an alkylene group, as defined above, having o to p carbon atoms.
  • Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cycloppentylethyl, cyclopentylpro- pyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, and the like.
  • C3-C6-cycloalkoxy refers to a cycloalkyl group, as defined above, having 3 to 6 carbon atoms, which is bound to the remainder of the molecule via an oxygen atom.
  • Examples of C3-C6-cycloalkoxy groups include cycloproppyloxy, cyclopentyloxy, cyclohexyloxy and the like.
  • Cs-Cio-cycloalkenyl-Ci-Cs-alkyl refers to cycloalkenyl as defined above which is bound via an alkylene group, as defined above, having 1 to 5 carbon atoms to the remainder of the molecule. Examples include but are not limited to cyclopentenyl- methyl, cyclopentenylethyl, cyclohexenylpropyl, cyclohexenylpentyl, cycloheptenyl- methyl, and the like.
  • halocycloalkyl as used herein and in the halocycloalkyl moieties of halo- cycloalkylmethyl denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms or 3 to 6 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are 1 - and 2- fluorocyclopropyl, 1 ,2-, 2,2- and
  • alkenyl denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, preferably 2 to 4 carbon atoms, e.g. vinyl, allyl (2-propen-1 -yl), 1 -propen-1 -yl, 2-propen-2-yl, methallyl (2-methylprop-2-en-1 -yl), 2-buten-1 -yl, 3-buten-1 -yl, 2-penten-1 -yl, 3-penten-1 -yl, 4-penten-1 -yl, 1 -methylbut-2- en-1 -yl, 2-ethylprop-2-en-1 -yl and the like.
  • haloalkenyl as used herein, which may also expressed as "alkenyl which may be substituted by halogen", and the haloalkenyl moieties in haloalkenyloxy, haloalkenylcarbonyl and the like refers to unsaturated straight-chain or branched hy- drocarbon radicals having 2 to 10 ("C 2 -Ci 0 -haloalkenyl") or 2 to 4 (“C 2 -C 4 -haloalkenyl”) carbon atoms and a double bond in any position, 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 unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 10, preferably 2 to 4 carbon atoms and one or two triple bonds in any position, e.g. ethynyl, propargyl (2-propyn-1 -yl), 1 -propyn-1 -yl, 1 - methylprop-2-yn-1 -yl), 2-butyn-1 -yl, 3-butyn-1 -yl, 1 -pentyn-1 -yl, 3-pentyn-1 -yl, 4- pentyn-1 -yl, 1 -methylbut-2-yn-1 -yl, 1 -ethylprop-2-yn-1 -yl and the like.
  • C3-Cio-haloalkynyl as used herein, which is also expressed as “C3-C10- alkynyl which may be substituted by halogen ", refers to unsaturated straight-chain or branched hydrocarbon radicals having 3 to 10 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;
  • alkoxyalkyl refers to alkyl usually comprising 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 10, in particular 1 to 4, carbon atoms as defined above. Examples are CH2OCH3, CH2-OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n-butoxymethyl, (l -methylpropoxy)-methyl,
  • alkylthio (also alkylsulfanyl or alkyl-S-)" as used herein refers to a straight- chain or branched saturated alkyl group comprising 1 to 10 carbon atoms
  • haloalkylthio refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
  • 3- to 6-membered carbocyclic ring refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings.
  • aryl refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.
  • saturated 3- to 10-membered heterocyclic ring e.g. "saturated 4-, 5- or 6- membered heterocyclic ring” includes in general 3-, 4-, 5-, 6-, 7- or 8- membered, in particular 4-, 5-, 6- or 7-membered monocyclic heterocyclic non-aromatic rings and 8- to 10-membered bicyclic heterocyclic non-aromatic rings, the mono- and bicyclic non- aromatic radicals may be saturated or unsaturated.
  • the mono- and bicyclic heterocyclic non-aromatic rings usually comprise 1 , 2, 3 or 4 heteroatoms, in particular 1 ,2 or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2.
  • saturated or unsaturated 3-, 4-, 5-, 6-, 7- or 8-membered heterocyclic rings comprise saturated or unsaturated, non- aromatic heterocyclic rings, such as oxirane, oxetane, thietane, thietane-S-oxid (S- oxothietane), thietane-S-dioxid (S-dioxothiethane), pyrrolidine, pyrazoline, imidazoline, pyrroline, pyrazoline, tetrahydrofurane, dihydrofurane, 1 ,3-dioxolane, dioxolene, thiolane, S-oxothiolane, S-dioxothiolane, dihydrothiene,
  • non- aromatic heterocyclic rings such as oxirane, oxetane, thietane, thietane-S-oxid (S- oxothietane
  • heteroaryl includes in general 5- or 6-membered unsaturated monocyclic heterocyclic radicals and 8 to 10 membered unsaturated bicyclic heterocyclic radicals which are aromatic, i.e. they comply with Huckel's rule (4n+2 rule). Heteroaryl usually comprise 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring members. Examples of 5- or 6-membered heteroaromatic radicals include pyridyl, i.e. 2-, 3-, or
  • heteroaryl also includes bicyclic 8- to 10-membered heteroaromatic radicals comprising as ring members 1 , 2 or 3 heteroatoms selected from N, O and S, wherein a 5- or 6-membered heteroaromatic ring is fused to a phenyl ring or to a 5- or
  • 6-membered heteroaromatic radical examples include benzofuranyl, benzothienyl, indolyl, indazolyl, benzimidazolyl, benzoxathiazolyl, ben- zoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, isochinolinyl, purinyl,
  • fused heteroaryl radicals may be bonded to the remainder of the molecule via any ring atom of 5- or 6-membered heteroaromatic ring or via a carbon atom of the fused phenyl moiety.
  • the remarks made below as to preferred embodiments of the variables (substituents) of the compounds of formulae I or II are valid on their own as well as preferably in combination with each other.
  • the invention relates to compounds of the formulae I or II, where R 5 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C 2 -C 6 -alkynyl, C(0)R c , C(S)R C , C(0)OR a , C(0)NR a R b , C(S)NR a R b , NR e R f , where the aforementioned alkyl, cycloalkyl, alkenyl and alkynyl radicals are unsubsti- tuted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d ,
  • aryl or heteroaryl phenyl-Ci-C4-alkyl or heteroaryl-Ci-C4-alkyl, wherein the rings of the four last mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R.
  • R 5 is selected from 5- or 6-membered saturated heterocyclyl-Ci-C6-alkyl, wherein the ring of the last mentioned radical may carry 1 , 2, 3, 4 or 5 substituents R.
  • R 5 , R 6 , R 7 and R 8 have the following meanings:
  • R 5 and R 6 are, independently of each other, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, wherein the four last mentioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d , wherein R d has the aforementioned meanings in particular those indicated herein as preferred;
  • aryl or heteroaryl phenyl-Ci-C4-alkyl or heteroaryl-Ci-C4-alkyl, wherein the rings of the four last mentioned radicals may carry 1 , 2, 3, 4 or 5 substituents R, wherein R has the aforementioned meanings in particular those indicated herein as preferred.
  • R 5 and R 6 are, independently of each other, 5- or 6- membered saturated heterocyclyl-Ci-C6-alkyl where heterocyclyl comprises, in addition to carbon ring members, two oxygen atoms as ring members and where the heterocyclyl moiety of heterocyclyl-Ci-C6-alkyl is unsubstituted or carries 1 , 2, 3, 4 or 5 substituents R, wherein R has the aforementioned meanings in particular Ci-C4-alkyl.
  • R 5 and R 6 preferably are, independently of each other, selected from Ci-C4-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, wherein the four last mentioned radicals are unsubstituted, partly or completely halogenated, phenyl-Ci-C4-alkyl and heteroaryl-Ci-C4-alkyl, wherein the rings of the four last mentioned radicals may carry 1 , 2 or 3 substitents selected from halogen, Ci-C4-alkyl and C1-C4- alkoxy.
  • R 5 and R 6 are, independently of each other, se- lected from 1 ,3-dioxolan-2-yl-Ci-C6-alkyl and 1 ,3-dioxan-2-yl-Ci-C6-alkyl, wherein the rings of the two last-mentioned radicals may carry 1 , 2, 3 or 4 Ci-C4-alkyl groups.
  • R 5 and R 6 particularly preferred are, independently of each other, selected from Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, wherein the three last mentioned radi- cals may be substituted with 1 , 2 or 3 halogen atoms, phenyl-Ci-C3-alkyl and heteroaryl-Ci-C4-alkyl, wherein the two last mentioned radicals may be substituted with 1 ,2 or 3 substituents selected from halogen, Ci-C3-alkyl and C1-C4- alkoxy.
  • R 5 and R 6 particularly preferred are, independently of each other, selected from 1 ,3-dioxolan-2-yl-Ci-C6-alkyl and 1 ,3-dioxan-2-yl-Ci-C6-alkyl, wherein the rings of the two last-mentioned radicals may carry 1 , 2, 3 or 4 C1-C4- alkyl groups.
  • R 5 and R 6 in particular are, independently of each other, methyl, ethyl, propyl, isopropyl, 2-methylpropyl, 2-methylbutyl, fluoromethyl, difluoromethyl, trifluoro- methyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3,-trifluoropropyl, allyl, 3-butenyl, 2-propynyl (propargyl), 3-butynyl, benzyl, chlorobenzyl, dichloro- benzyl, fluorobenzyl, difluorobenzyl, pyridin-2yl-methyl, pyridin-3yl-methyl, 2-[1 ,3]- dioxan-2-yl-ethyl, 2-[1 ,3]dioxolan-2-yl-ethyl, 2-(bromophenyl)-ethyl and specifically
  • R 5 and R 6 independently of each other, form a moiety together with R 10 , as further described herein below.
  • R 7 is hydrogen, OH, cyano, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl,
  • radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d , wherein R d has the aforementioned meanings in particular those indicated herein as preferred;
  • R 7 preferably is hydrogen, Ci-C4-alkyl, C3-C6-cycloalkyl, wherein the two last mentioned radicals are unsubstituted, partly or completely halogenated, C(0)-Ci-
  • R 7 particularly preferred is hydrogen, Ci-C4-alkyl, C3-C6-cycloalkyl, wherein the two last mentioned radicals may be substituted with 1 , 2 or 3 halogen atoms,
  • R 7 in particular is hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, acetyl, benzyl, and specifically is hydrogen, methyl, ethyl, or benzyl.
  • R 7 forms a moiety together with R 8 or R 10 as further described herein below.
  • R 8 is hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl or C2-C6-alkenyl, wherein the two last mentioned radicals are unsubstituted, partly or completely halogenated.
  • R 8 preferably is hydrogen, Ci-C4-alkyl or C3-C6-cycloalkyl.
  • R 8 in particular is hydrogen, methyl, ethyl or propyl, and specifically is hydrogen or methyl.
  • R 8 forms a moiety together R 10 as further described herein below.
  • R 7 and R 8 together with the nitrogen atom they are attached to, form a saturated or unsaturated, N-bound, 5-, 6- or 7-membered heterocyclic ring, optionally containing an additional heteroatom selected from N, O and S, whereas each of the carbon atoms of the heterocyclic ring may optionally carry any combination of 1 or 2 radicals selected from halogen, Ci-C4-alkyl and Ci-C4-alkoxy, and whereas the additional N-atom, if present, carries a radical selected from hydrogen, Ci-C4-alkyl and C3-C6-cycloalkyl,
  • R 7 and R 8 in this context preferably form, together with the nitrogen atom they are attached to, a saturated or unsaturated, N-bound, 5-or 6-membered heterocyclic ring, wherein each of the carbon atoms of the heterocyclic ring may optionally carry 1 or 2 radicals selected from chlorine, fluorine, methyl, ethyl and methoxy.
  • R 7 and R 8 in this context more preferably represent a linear C4-Cs-alkandiyl moiety which is unsubstituted or may carry 1 , 2 or 3 radicals selected from chlorine, fluorine and methyl, and specifically represent a n-butandiyl or a n-pentandiyl moiety.
  • R 10 is hydrogen, OH, cyano, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl,
  • radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d , wherein R d has the aforementioned meanings in particular those indicated herein as preferred;
  • R 10 preferably is hydrogen, Ci-C4-alkyl, C3-C6-cycloalkyl, wherein the two last mentioned radicals are unsubstituted, partly or completely halogenated, C(0)-Ci- C 4 -alkyl, C(S)-Ci-C -alkyl, C(0)0-Ci-C -alkyl, C(0)NH 2 , C(0)NH-Ci-C 4 -alkyl, C(0)N-di-Ci-C 4 -alkyl or phenyl-Ci-C3-alkyl, wherein the phenyl radical may carry 1 , 2 or 3 substitents selected from halogen, Ci-C3-alkyl and Ci-C3-alkoxy.
  • R 10 particularly preferred is hydrogen, Ci-C 4 -alkyl, C3-C6-cycloalkyl, wherein the two last mentioned radicals may be substituted with 1 , 2 or 3 halogen atoms,
  • R 10 in particular is hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, fluoro- methyl, difluoromethyl, trifluoromethyl, and specifically is hydrogen.
  • R 10 and one of R 5 , R 6 or R 7 or R 8 together form a linear C2-C 4 -alkandiyl or C2-C 4 -alkendiyl moiety whereas one of the carbon atoms of C2-C 4 -alkandiyl or C2-C 4 -alkendiyl may be replaced by a carbonyl group or a heteroatom selected from O, S, N and N-R h , with R h being selected from hydrogen, Ci-C 4 -alkyl and C3- C6-cycloalkyl,
  • C2-C 4 -alkandiyl and C2-C 4 -alkendiyl moieties are unsubstituted or may carry 1 , 2 or 3 radicals selected from halogen, Ci-C 4 -alkyl and Ci-C 4 - alkoxy.
  • R 10 and one of R 5 , R 6 , R 7 or R 8 preferably form a linear C2-C3- alkandiyl or C2-C3-alkendiyl moiety whereas one of the carbon atoms of C2-C3- alkandiyl or C2-C3-alkendiyl may be replaced by a carbonyl group or a heteroatom selected from O, S, N and N-H, and whereas the C2-C3-alkandiyl and C2-C3- alkendiyl moieties are unsubstituted or may carry 1 , 2 or 3 radicals selected from chlorine, fluorine, methyl and ethyl.
  • R 10 and one of R 5 , R 6 , R 7 or R 8 in particluar form a linear C2-C3- alkandiyl moiety whereas one of the carbon atoms of C2-C3-alkandiyl may be replaced by a carbonyl group and whereas the C2-C3-alkandiyl moiety is unsubstituted or may carry 1 , 2 or 3 radicals selected from chlorine, fluorine and methyl, and specifically form a moiety -CH2-C(0)- or -CH2-CH2-C(0)-.
  • the invention relates to compounds of the formulae I or II, where Het is selected from a 5- or 6- membered C-bound or N-bound saturated, unsaturated or aromatic heterocycle, having at least one heteroatom group, selected from O, S, N and N-X, as ring member and optionally 1 or 2 further N atoms as ring member, where the heterocycle is unsubstituted or carries at its carbon atoms 1 or 2 radi- cals Y, wherein X and Y are as defined above.
  • Het is selected from a 5- or 6- membered C-bound or N-bound saturated, unsaturated or aromatic heterocycle, having at least one heteroatom group, selected from O, S, N and N-X, as ring member and optionally 1 or 2 further N atoms as ring member, where the heterocycle is unsubstituted or carries at its carbon atoms 1 or 2 radi- cals Y, wherein X and Y are as defined above.
  • Het is a 5- or 6- membered C-bound saturated, unsaturated or aromatic heterocycle, having at least one heteroatom group, selected from O, S and N-X, as ring member and optionally 1 or 2 further N atoms as ring member, where the heterocycle is unsubstituted or carries at its carbon atoms 1 or 2 radicals Y, wherein X and Y are as defined above.
  • Het is selected from a 5- or 6- membered C-bound saturated, unsaturated or aromatic heterocycle, having at least one heteroatom group, selected from O, N, S and N-X, as ring member and optionally 1 or 2 further N atoms as ring member, where the heterocycle is unsubstituted or carries at its carbon atoms 1 or 2 radicals Y, wherein X and Y are as defined above.
  • Het is selected from a a 5- or 6- membered N-bound saturated, unsaturated or aromatic heterocycle, having at least one heteroatom group, selected from O, N, S and N-X, as ring member and optionally 1 or 2 further N atoms as ring member, where the heterocycle is unsubstituted or carries at its carbon atoms 1 or 2 radicals Y, wherein X and Y are as defined above.
  • Het in formulae I or II is selected from the group consisting of radicals of formulae Het-1 to Het-24:
  • Het-1) Het-2) (Het-3) (Het-4) (Het-5)
  • p and q are, independently of each other, 0, 1 or 2, and in particular 0 or 1 ;
  • X is hydrogen, Ci-C6-haloalkyl, C2-C6-haloalkenyl, Ci-C6-alkyl, C3-C6-cycloalkyl, C2- C6-alkenyl, wherein the three last mentioned radicals may carry any combination of 1 , 2 or 3 radicals R d , wherein R d has the aforementioned meanings in particular those indicated herein as preferred;
  • X preferably is hydrogen, Ci-C4-haloalkyl, Ci-C4-alkyl, C3-C6-cycloalkyl, wherein the two last mentioned radicals may carry 1 , 2 or 3 radicals selected from nitro, cyano, Ci-C4-alkoxy, C(0)-Ci-C4-alkyl, N H2, NH-Ci-C4-alkyl, phenyl and benzyl, C(0)-Ci-C 4 -alkyl, C(0)0-Ci-C -alkyl, C(0)NH 2 , C(0)NH-Ci-C 4 -alkyl or C(0)N-di-
  • Ci-C 4 -alkyl Ci-C 4 -alkyl
  • X particularly preferred is hydrogen, Ci-C4-haloalkyl, Ci-C4-alkyl, which may carry 1 , 2 or 3 radicals selected from nitro, cyano, Ci-C3-alkoxy and C(0)-Ci-C3-alkyl, C(0)-Ci-C 4 -alkyl or benzyl.
  • X in particular is hydrogen, methyl, ethyl, propyl, isopropyl, fluoromethyl, di- fluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, acetyl, benzyl, and specifically is hydrogen, methyl, ethyl, or benzyl.
  • Y and Y' are, independently of each other, halogen, Ci-C6-alkyl, Ci-C4-haloalkyl, C3- C6-cycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C2- C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, CN, NO2, C(0)R c , C(0)OR a or C(0)NR a R b , wherein R c , R a and R have the aforementioned meanings in particular those indicated herein as preferred;
  • Y and Y' preferably are, independently of each other, selected from halogen, Ci- C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4- alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, CN, N0 2 , C(0)-Ci-C 4 -alkyl, C(0)0-Ci- C 4 -alkyl, C(0)NH 2 , C(0)NH-Ci-C 4 -alkyl and C(0)N-di-Ci-C 4 -alkyl.
  • Y and Y' particularly preferred are, independently of each other, selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, CN, NO2 and methylcarbonyl.
  • Y and Y' in particular are, independently of each other, selected from bromine, chlordine, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, allyl, 3-butenyl, methoxy, ethoxy, propoxy, CN and NO2, and specifically selected from chlorine, fluorine, methyl, ethyl, propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2- difluoroethyl and 2,2,2-trifluoroethyl.
  • Het in formulae I or II is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24:
  • Y is selected from halogen, Ci-C4-haloalkyl or Ci-C4-alkyl, specifically from chlorine, fluorine, methyl, ethyl, propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl and 2,2,2-trifluoroethyl;
  • p and q independently of each other, are 0, 1 or 2 and specifically are 0 or 1 ;
  • Y' is selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl or C2-C6-alkynyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2- C6-alkynyloxy, Ci-C6-haloalkoxy or Ci-C6-alkylthio; particularly selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, Ci-C4-alkoxy and C1-C4- haloalkoxy, and specifically from chlorine, fluorine, methyl, ethyl, propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl,
  • R 1 and R 2 are, independently of each other, hydrogen, halogen, CN , NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C4-alkynyl, Ci-C6-alkoxy, wherein the five last mentioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d , wherein R d has the aforementioned meanings in particular those indicated herein as preferred,
  • R 1 and R 2 preferably are, independently of each other, hydrogen, halogen, CN , NO2, Ci-C4-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, wherein the four last mentioned radicals are unsubstituted, partly or completely halogenated, C(0)-Ci-C 4 -alkyl, C(0)0-Ci-C 4 -alkyl, C(0)NH 2 , C(0)NH-Ci-C 4 -alkyl or C(0)N-di- Ci-C 4 -alkyl.
  • R 1 and R 2 particularly preferred are, independently of each other, hydrogen, halogen, Ci-C 4 -alkyl, C2-C 4 -alkenyl, C2-C 4 -alkynyl, wherein the three last mentioned radicals may be substituted with 1 , 2 or 3 halogen atoms, C(0)-Ci-C 4 -alkyl or C(0)0-Ci-C 4 -alkyl.
  • R 1 and R 2 in particular are, independently of each other, hydrogen, chlorine, fluorine, methyl, ethyl, propyl, isopropyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, allyl, 3-butenyl, 2-propynyl, 3- butynyl, C(0)-Ci-C3-alkyl or C(0)0-Ci-C3-alkyl, and specifically hydrogen, methyl, ethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, allyl or 2-propynyl.
  • R 1 and R 2 together with the carbon atom they are attached to, form a 3- to 6-membered saturated carbocycle, wherein each of the carbon atoms of said carbocycle are unsubstituted or may carry any combination of 1 or 2 radicals selected from halogen, Ci-C 4 -alkyl, C2-C 4 -alkyl and Ci-C 4 -alkoxy.
  • R 1 and R 2 in this context preferably, together with the carbon atom they are attached to, form a 3-or 5-membered saturated carbocycle, wherein said carbocycle may optionally be substituted with 1 , 2 or 3 radicals selected from chlorine, fluorine, methyl, ethyl and methoxy and specifally form, together with the carbon atom they are attached to, a cyclopropane or cyclobutane ring.
  • R 3 is hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, wherein the three last mentioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d , wherein R d has the aforementioned meanings in particular those indicated herein as preferred;
  • R 3 preferably is hydrogen, Ci-C 4 -alkyl, C3-C6-cycloalkyl, wherein the two last mentioned radicals are unsubstituted, partly or completely halogenated, C(0)-Ci- C 4 -alkyl, C(0)0-Ci-C 4 -alkyl, C(0)NH 2 , C(0)NH-Ci-C 4 -alkyl or C(0)N-di-Ci-C 4 - alkyl.
  • R 3 particularly preferred is hydrogen, Ci-C 4 -alkyl, C3-C6-cycloalkyl, wherein the two last mentioned radicals may optionally be substituted with 1 , 2 or 3 halogen atoms, C(0)-Ci-C 4 -alkyl, C(0)NH 2 or C(0)NH-Ci-C 4 -alkyl.
  • R 3 in particular is hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopro- pyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or acetyl, and specifically is hydrogen, methyl, ethyl, propyl, isopropyl, tert-butyl or cyclopropyl.
  • R 3 forms a moiety together with R 4 as further described herein below.
  • R 4 is NR e R f , Ci-C6-alkyl, C3-C6-cycloalkyl, wherein the two last mentioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d , wherein R d has the aforementioned meanings in particular those indicated herein as preferred.
  • R 4 preferably is Ci-C4-alkyl, C3-C6-cycloalkyl, wherein Ci-C4-alkyl and C3-C6- cycloalkyl are unsubstituted, partly or completely halogenated, N H2, NH-C1-C4- alkyl or N-di-Ci-C 4 -alkyl.
  • R 4 particularly preferred is Ci-C 4 -alkyl, C3-C6-cycloalkyl, wherein Ci-C 4 -alkyl and C3-C6-cycloalkyl may optionally be substituted with 1 , 2 or 3 halogen atoms, N H2, NH-Ci-C 3 -alkyl or N-di-Ci-C 3 -alkyl.
  • R 4 in particular is methyl, ethyl, propyl, isopropyl, cyclopropyl, fluoromethyl, di- fluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, or
  • N H2 and specifically is methyl, ethyl or propyl.
  • R 3 and R 4 together with the nitrogen and sulfur atoms to which they are bound, form a saturated or unsaturated, 4-, 5- or 6-membered heterocyclic ring, optionally containing an additional heteroatom selected from N, O and S, whereas each of the carbon atoms of the heterocyclic ring may optionally carry any combination of 1 or 2 radicals selected from halogen, Ci-C 4 -alkyl and C1-C4- alkyl, and whereas the additional N-atom, if present, carries a radical selected from hydrogen, Ci-C 4 -alkyl and C3-C6-cycloalkyl,
  • R 3 and R 4 in this context preferably form, together with the nitrogen and sulfur atoms to which they are bound, a saturated or unsaturated, 4-, 5- or 6-membered heterocyclic, optionally containing an additional heteroatom selected from N and O, wherein each of the carbon atoms of the heterocyclic ring may optionally carry 1 or 2 radicals selected from chlorine, fluorine, methyl, ethyl, methoxy and ethoxy and whereas the additional N-atom, if present, carries a radical selected from hydrogen, methyl, ethyl and propyl.
  • R 3 and R 4 in this context more preferably represent a linear C2-C 4 -alkandiyl moiety whereas the C2-C 4 -alkandiyl moiety is unsubstituted or may carry 1 , 2 or 3 radicals selected from chlorine, fluorine and methyl, and specifically represent an ethandiyl, a n-propandiyl or a n-butandiyl moiety.
  • a particular embodiment of the present invention relates to compounds of the present invention, wherein B is S and A is NR 7 R 8 with R 7 and R 8 having the meanings given herein, in particular the ones mentioned as preferred.
  • R 7 is preferably selected from hydrogen, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, C(0)R c , C(S)R C , C(0)OR a ,
  • Ci-C 6 -alkyl and C 3 -C 6 -cycloalkyl are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d , and more preferably is selected from hydrogen and Ci-C6-alkyl, wherein R a , R b , R c and R d are as defined herein; and R 8 is preferably selected from hydrogen and Ci-C6-alkyl and more preferably is hydrogen.
  • a further particular embodiment of the present invention relates to compounds of the present invention and to their salts, wherein B is NR 10 and A is SR 6 with R 10 and R 6 having the meanings given herein, in particular the ones mentioned as preferred.
  • R 10 is preferably selected from hydrogen, Ci-C6-alkyl or C3-C6-cycloalkyl, wherein Ci-C6-alkyl and C3-C6-cycloalkyl are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d , and more preferably is hydrogen, wherein R d is as defined herein; and R 6 is preferably selected from C1-C6- alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein Ci-C6-alkyl, C3-C6- cycloalkyl, C2-C6-alkenyl and C2-C6-al
  • R 10 and R 6 together form a linear C2-C3-alkandiyl moiety wherein one of the carbon atoms of C2-C3-alkandiyl may be replaced by a car- bonyl group and whereas the C2-C3-alkandiyl moiety is unsubstituted or may carry 1 , 2 or 3 radicals selected from chlorine, fluorine and methyl, and specifically together form a moiety -CH 2 -C(0)- or -CH 2 -CH 2 -C(0)-.
  • a further particular embodiment of the present invention relates to compounds of the present invention, wherein the variable n is 0.
  • a further particular embodiment of the present invention relates to compounds of the present invention, wherein the variable n is 1 and R 1 and R 2 are independently from one another selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl or C3-C6-cycloalkyl.
  • a further particular embodiment of the present invention relates to compounds of the present invention, wherein R 3 and R 4 together represent a linear C2-C4-alkandiyl moiety, such as CH2CH2, CH2CH2CH2 or CH2CH2CH2CH2.
  • a further particular embodiment of the present invention relates to compounds of the present invention, wherein
  • Ci-C4-alkyl and Ci-C4-haloalkyl are selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, preferably from halogen and Ci-C4-haloalkyl, and
  • A is NR 7 R 8 , wherein R 7 and R 8 are as defined herein and each preferably has one of the meanings given below,
  • n 0 or 1 ;
  • R 1 , R 2 are independently from one another selected from the group consisting of hydrogen, methyl, ethyl and trifluoromethyl, or
  • R 1 and R 2 together with the carbon atom which they are attached to form a cyclopropane ring
  • R 3 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, tert-butyl and cyclopropylmethyl;
  • R 4 is methyl or ethyl
  • R3 and R 4 together form CH 2 CH 2 , CH 2 CH 2 CH 2 or CH 2 CH 2 CH 2 CH 2 CH 2 ;
  • R 7 is hydrogen, Ci-C 6 -alkyl, C(0)R c , C(S)R C , C(0)OR a , C(0)NR a R b , or C(S)NR a R b , wherein R a , R b and R c are as defined herein; and
  • R 8 is hydrogen or Ci-C6-alkyl.
  • A is NR 7 R 8 , wherein R 7 is hydrogen or Ci-C6-alkyl and R 8 is hydrogen;
  • n 0;
  • R 3 and R 4 together form CH 2 CH 2 , CH 2 CH 2 CH 2 or CH 2 CH 2 CH 2 CH 2 .
  • a further particular embodiment of the present invention relates to compounds of the present invention, wherein
  • Y is selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, preferably from halogen and Ci-C4-haloalkyl, and
  • p 0, 1 or 2, and preferably is 1 ;
  • R 10 is as defined herein and preferably has one of the meanings given below;
  • A is S-R 6 , wherein R 6 is as defined herein and preferably has one of the meanings given below;
  • n 0 or 1 ;
  • R 1 , R 2 are independently from one another selected from the group consisting of hydrogen, methyl, ethyl and trifluoromethyl, or
  • R 1 and R 2 together with the carbon atom which they are attached to form a cyclopropane ring
  • R 3 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, cyclopropyl, tert-butyl and cyclopropylmethyl;
  • R 4 is methyl or ethyl
  • R 3 and R 4 together form CH 2 CH 2 , CH 2 CH 2 CH 2 or CH 2 CH 2 CH 2 CH 2 CH 2 ;
  • R 6 is selected from the group consisting of Ci-C6-alkyl, C3-C6-cycloalkyl, C 2 -C6- alkenyl, C 2 -C6-alkynyl, wherein Ci-C6-alkyl, C3-C6-cycloalkyl, C 2 -C6-alkenyl and C 2 -C6-alkynyl are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d ,
  • R 6 is selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, in particular selected from Ci-C3-alkyl, C 2 -C4-alkenyl and C 2 -C4- alkynyl, and specifically from methyl, ethyl, isopropyl, 2-methylpropyl, 2- methylbutyl, 3,3,3,-trifluoropropyl, allyl, propagyl, and 3-butynyl;
  • R 6 is selected from ([1 ,3]-dioxan-2-yl)-d-C 6 -alkyl, ([1 ,3]dioxolan-2- yl)-Ci-C6-alkyl, where the rings of the two last-mentioned radicals may carry 1 , 2, 3 or 4 Ci-C4-alkyl groups, and phenyl-Ci-C 2 -alkyl, wherein the phenyl ring carries 1 or 2 halogen atoms, and specifically2-([1 ,3]dioxolan-2-yl)-ethyl, 4-chlorobenzyl and 2-(4-bromophenyl)-ethyl,
  • R d is preferably selected from Ci-C 4 -alkyl, NR e R f , C(0)R c , C(S)R C , C(0)OR a ,
  • R is preferably selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, NR e R f , C(0)R c , C(S)R C , C(0)OR a , C(0)NR a R b , C(S)NR a R , S(0) m R c and S(0) m NR a R R d , and more preferably selected from Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, C(0)-Ci-C 4 -alkyl, C(S)-Ci-C 4 -alkyl, C(0)0-Ci-C 4 -alkyl, C(0)NH 2 , C(0)NH-Ci-C 4 -alkyl
  • R 10 is selected from the group consisting of hydrogen, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R d , C(0)R c , C(S)R C , C(0)OR a , C(0)NR a R b , or C(S)NR a R ,
  • R 10 is selected from hydrogen and Ci-C6-alkyl which is unsubstituted or partly or completely halogenated, and particularly preferred is methyl or hydrogen,
  • R a , R b , R d and R d are as defined herein and R d is preferably Ci-C4-alkyl, C(0)-Ci-C 4 -alkyl, C(S)-Ci-C 4 -alkyl, C(0)0-Ci-C 4 -alkyl, C(0)NH 2 , C(0)N H-Ci-C 4 - alkyl or C(0)N-di-Ci-C4-alkyl, R a and R b , independently of each other are preferably hydrogen, Ci-C4-alkyl or Ci-C4-haloalkyl, and R c preferably is Ci-C4-alkyl or Ci-C4-haloalkyl.
  • Particularly preferred compounds I and II of the directly preceding embodiment are those wherein
  • n 0;
  • R 3 and R 4 together form CH 2 CH 2 , CH 2 CH 2 CH 2 or CH 2 CH 2 CH 2 CH 2 .
  • a further particular embodiment of the present invention relates to compounds of the present invention, wherein the variable Het is selected from the moieties 6- halogenpyridin-3-yl and 6-(Ci-C4-haloalkyl)pyridin-3-yl.
  • the variables R 9a , R 9b , R 9c , R a , R b , R c , R d , R e , R f , Ra, R h , R and m independently of each other, preferably have one of the following meanings:
  • R 9a and R 9b are independently of each other selected from hydrogen, halogen and Ci- C4-alkyl, or R 9a and R 9b together with the carbon atom to which they bound from a 5- or 6-membered heterocyclic ring.
  • R 9a and R 9b are independently of each other selected from hydrogen and halogen, such as chlorine or fluorine.
  • R 9c is selected from hydrogen, halogen, Ci-C4-alkyl and N0 2 , in particular from hydrogen and halogen, such as chlorine or fluorine.
  • R a and R b are independently of each other selected from hydrogen, Ci-C4-alkyl, C3-C6- cycloalkyl and Ci-C4-haloalkyl;
  • R c is selected from Ci-C4-alkyl, C3-C6-cycloalkyl and Ci-C4-haloalkyl;
  • R d is selected from Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C(0)-Ci-C 4 -alkyl, C(0)NH 2 , phenyl and benzyl;
  • R e , R f , R h are independently of each other selected from hydrogen, Ci-C4-alkyl, C1-C4- haloalkyl or
  • R e and R f together with the nitrogen atom they are attached to, form a saturated N- bound, 5- or 6-membered heterocyclic ring, which optionally contains an additional heteroatom selected from N, O and S, e.g. pyrrolidin-1 -yl, piperidin-1 -yl, morpholin-4-yl, piperazin-1 -yl or 4-methylpiperazin-1 -yl;
  • Ra, R are independently of each other selected from halogen, Ci-C4-alkyl, C1-C4- haloalkyl, C(0)-Ci-C 4 -alkyl, C(0)NH 2 , phenyl and benzyl; and m is 1 or 2;
  • a particular embodiment of the present invention relates to compounds of formulae I and II wherein the variables R 3 and R 4 together form a moiety CH2-CH2-CH2 or a moiety CH2-CH2-CH2-CH2, that are hereunder denoted compounds of the general formulae l-c and ll-c,
  • variable s is 1 or 2 and the variables n, Het, R 1 , R 2 , A and B are as defined herein and in particular have the meanings mentioned herein as preferred.
  • Particular preferred compounds of the formulae l-c and ll-c are those of the general formulae l-Ac, ll-Ac, l-Bc and ll-Bc,
  • variable s is 1 or 2 and the variables n, Het, R 1 , R 2 , A and B are as defined herein and in particular have the meanings mentioned herein as preferred.
  • the compounds of the general formula l-Aa which are indicated in Tables 1 to 72 below, and their enantiomers, diastereomers and agriculturally or veterinarily acceptable salts, represent per se preferred embodiments of the present invention.
  • the meanings for Het, R 3 and R 4 indicated in Table A below represent embodiments of the invention which are likewise preferred independently of one another and especially in combination.
  • Table 48 Compounds of the formula l-Aa in which R 1 is methyl n, R 2 is hydrogen, R 7 is isopropyl, R 8 is ethyl, and the combination of Het, R 3 and R 4 for a compound in each case corresponds to one line of Table A.
  • Table 49 Compounds of the formula l-Aa in which R 1 is methyl n, R 2 is hydrogen, R 7 is isopropyl, R 8 is ethyl, and the combination of Het, R 3 and R 4 for a compound in each case corresponds to one line of Table A.
  • Table 49 Compounds of the formula l-Aa in which R 1 is methyl n, R 2 is hydrogen, R 7 is isopropyl, R 8 is ethyl, and the combination of Het, R 3 and R 4 for a compound in each case corresponds to one line of Table A.
  • Table 1 19 Compounds of the formula l-Ba in which R 1 is methyl, R 2 is methyl, R 6 is propagyl, R 10 is methyl, and the combination of Het, R 3 and R 4 for a compound in each case corresponds to one line of Table A.
  • Table 120
  • Table 141 Compounds of the formula l-Bb in which R 6 is allyl, R 10 is hydrogen, and the combination of Het, R 3 and R 4 for a compound in each case corresponds to one line of Table A.
  • the compounds of the formulae I or II can be prepared by the standard methods of organic chemistry, e.g. by the methods described hereinafter or in the working exam- pies.
  • LG represents a nucleophilically displaceable leaving group, such as halogen, e.g. chlorine or bromine, or tosylate.
  • Sulfinamidines II-5 can be converted to the respective sulfonimidamides I-5 by oxidation using mefa-chloroperbenzoic acid in the presence of a base such as potassium carbonate (K2CO3) or using sodium periodate (Nal0 4 ) in combination with ruthenium trichloride (RuC ).
  • a base such as potassium carbonate (K2CO3) or using sodium periodate (Nal0 4 ) in combination with ruthenium trichloride (RuC ).
  • Reaction of sulfenamides IV with iodosobenzene diacetate and trifluoroacetamide in the presence of a catalyst such as rhodium diacetate and a base such as magnesium oxide yields sulfinamidine derivaties II-6.
  • the reaction is preferably carried out in a polar aprotic solvent such as dichloromethane.
  • Oxidation of the sulfinamidines II-6 with mefa-chloroperbenzoic acid in the presence of a base or with aqueous sodium periodate in the presence of a catalyst such as ruthenium trichloride provides the corresponding sulfonimidamides I-6.
  • compounds of formula I wherein B is O and A is CR 9a R 9b R 9c can be prepared by conversion of sulfonimidamide derivatives ⁇ with an anhydride reagent in a nonprotic solvent, as shown in scheme 4.
  • the sulfinamides III and the sulfenamides IV are known in the art, are commercially available or can be prepared by methods described e.g. in WO2009/156336.
  • the compounds of formulae I or II including their salts, enantiomers and di- astereomers can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or II or by customary modifications of the synthesis routes described.
  • certain compounds I or II can ad- vantageously be prepared from other compounds I or II by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like.
  • reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel.
  • Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or trituration.
  • the compounds of the present invention may be used for controlling invertebrate pests.
  • the present invention also provides a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of the present invention or a composition as defined above.
  • the method of the invention serves for protecting plant propagation material (such as seed) and the plant which grows therefrom from invertebrate pest attack or infestation and comprises treating the plant propagation material (such as seed) with a pesticidally effective amount of a compound of the present invention as defined above or with a pesticidally effective amount of an agricultural composition as defined above and below.
  • the method of the invention is not limited to the protection of the "substrate" (plant, plant propagation materials, soil material etc.) which has been treated according to the invention, but also has a preventive effect, thus, for example, accord- ing protection to a plant which grows from a treated plant propagation materials (such as seed), the plant itself not having been treated.
  • invertebrate pests are preferably selected from arthropods and nematodes, more preferably from harmful insects, arachnids and nematodes, and even more preferably from insects, acarids and nematodes.
  • invertebrate pests are most preferably insects preferably insects of the order Homoptera.
  • the invention further provides an agricultural composition for combating such inverte- brate pests, which comprises such an amount of at least one compound of the present invention and at least one inert liquid and/or solid agronomically acceptable carrier that has a pesticidal action and, if desired, at least one surfactant.
  • Such a composition may contain a single active compound of the present invention or a mixture of several active compounds of the present invention.
  • the composition according to the present invention may comprise an individual isomer or mixtures of isomers as well as individual tautomers or mixtures of tautomers.
  • the compounds of the present invention and the pestidicidal compositions comprising them are effective agents for controlling arthropod pests and nematodes.
  • Invertebrate pests controlled by the compounds of the present invention include for example insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheima- tobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandi- osella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bou- liana, Feltia subterranea, Galleria mellonella, Grapholith
  • hymenopterans e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, So- lenopsis geminata and Solenopsis invicta
  • heteropterans Heteroptera
  • Acyrthosiphon onobrychis Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Bemisia tabaci, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae,
  • Arachnoidea such as arachnids (Acarina), e.g.
  • Argasidae such as Amblyomma americanum, Amblyomma variegatum, Argas persi- cus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus mou- bata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendi- culatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp.
  • Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis; siphonatera, e.g.
  • compositions and compounds of the present invention are useful for the control of nematodes, especially plant parasitic nematodes such as root knot nematodes, Meloi- dogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Het- erodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bur
  • the compounds of the present invention are used for controlling insects or arachnids, in particular insects of the orders Lepidoptera, Coleoptera, Thysanoptera and Homoptera and arachnids of the order Acarina.
  • insects or arachnids in particular insects of the orders Lepidoptera, Coleoptera, Thysanoptera and Homoptera and arachnids of the order Acarina.
  • the compounds of formulae I or II according to the present invention are particularly useful for controlling insects of the order Thysanoptera and Homoptera.
  • the compounds of the present invention or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by invertebrate pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of the present invention.
  • crop refers both to growing and harvested crops.
  • the compounds of the present invention can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention.
  • auxiliaries suitable for the formulation of agrochemicals such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, anti- foaming agents, anti-freezing agents, for seed treatment formulation also optionally colorants and/or binders and/or gelling agents.
  • solvents examples include water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone [NMP], N-octylpyrrolidone [NOP]), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.
  • aromatic solvents for example Solvesso products, xylene
  • paraffins for example mineral oil fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamma-butyrolactone
  • pyrrolidones N
  • Suitable emulsifiers are non-ionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates).
  • dispersants examples include ligninsulfite waste liquors and methylcellulose.
  • Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalene- sulfonic acid, alkylarylsulfonates, alkyl sulphates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulphated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyg
  • Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraf- fin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, etha- nol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene,
  • anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bacte- ricides such as can be added to the formulation.
  • Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.
  • a suitable preservative is e.g. dichlorophen.
  • Seed treatment formulations may additionally comprise binders and optionally colorants.
  • Binders can be added to improve the adhesion of the active materials on the seeds after treatment.
  • Suitable binders are block copolymers EO/PO surfactants but also polyvinylalcoholsl, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybute- nes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, poly- ethyleneimines (Lupasol ® , Polymin ® ), polyethers, polyurethans, polyvinylacetate, ty- lose and copolymers derived from these polymers.
  • colorants can be included in the formulation.
  • Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 1 12, C.I. Solvent Red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pig- ment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • gelling agent is carrageen (Satiagel ® ).
  • Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • solid carriers examples include mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertiliz- ers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertiliz- ers, such as, for example, ammonium sulfate, ammoni
  • the formulations comprise from 0.01 to 95 % by weight, preferably from 0.1 to 90 % by weight, of the active compound(s).
  • the active compound(s) are employed in a purity of from 90 % to 100% by weight, preferably 95 % to 100 % by weight (according to NMR spectrum).
  • respective formulations can be diluted 2- to10-fold lead- ing to concentrations in the ready to use preparations of 0.01 to 60 % by weight active compound by weight, preferably 0.1 to 40 % by weight.
  • the compounds of the present invention can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring.
  • the use forms depend entirely on the in- tended purposes; they are intended to ensure in each case the finest possible distribution of the active compound(s) according to the invention.
  • Aqueous use forms can be prepared from emulsion concentrates, pastes or wetable powders (sprayable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsi- fier.
  • concentrates composed of active substance, wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10 %, preferably from
  • the active compound(s) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95 % by weight of active compound, or even to apply the active compound without additives.
  • UUV ultra-low-volume process
  • the active compound(s) 10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. The active compound(s) dissolves upon dilution with water, whereby a for- mulation with 10 % (w/w) of active compound(s) is obtained.
  • Emulsions EW, EO, ES
  • 25 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25 % (w/w) of active compound(s) is obtained.
  • an emulsifier machine e.g. Ultraturrax
  • 75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s) , whereby a for- mulation with 75% (w/w) of active compound(s) is obtained.
  • Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.
  • the compounds of the present invention are also suitable for the treatment of plant propagation materials (such as seed).
  • Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1 to 800 g/l of active ingredient, 1 to 200 g/l surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • compositions of compounds of the present invention for seed treat- ment comprise from 0.5 to 80% wt of the active ingredient, from 0.05 to 5% wt of a wetting agent, from 0.5 to 15% wt of a dispersing agent, from 0.1 to 5% wt of a thickener, from 5 to 20% wt of an anti-freeze agent, from 0.1 to 2% wt of an anti-foam agent, from 1 to 20% wt of a pigment and/or a dye, from 0 to 15% wt of a sticker /adhesion agent, from 0 to 75% wt of a filler/vehicle, and from 0.01 to 1 % wt of a preservative.
  • the compounds of the present invention are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).
  • the compounds of the present invention are preferably used in a bait composition.
  • the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).
  • Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks.
  • Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spraying devices, droplet sources, or evapora- tion sources.
  • Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickiness, moisture retention or aging characteristics.
  • the bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitoes, crickets etc. or cock- roaches to eat it.
  • the attractiveness can be manipulated by using feeding stimulants or sex pheromones.
  • Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey.
  • Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant.
  • Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
  • Formulations of compounds of the present invention as aerosols e.g. in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches.
  • Aerosol recipes are preferably corn-posed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g.
  • paraffin hydrocar-bons e.g. kerosenes
  • paraffin hydrocar-bons having boiling ranges of approximately 50 to 250 °C
  • dimethyl-formamide N-methylpyrrolidone
  • dimethyl sulphoxide aromatic hydrocarbons such as toluene, xylene, water
  • auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3 to 7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if re- quired, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
  • emulsifiers such as
  • the oil spray formulations differ from the aerosol recipes in that no propellants are used.
  • the compounds of the present invention and their respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
  • Methods to control infectious diseases transmitted by insects with compounds of the present invention and their respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like.
  • Insecticidal compositions for application to fibers, fabric, knit- goods, non-wovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.
  • Suitable repellents for example are ⁇ , ⁇ -diethyl-meta-toluamide (DEET), N,N- diethylphenylacetamide (DEPA), 1 -(3-cyclohexan-1 -yl-carbonyl)-2-methylpiperine, (2- hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1 ,3-hexandiol, indalone, Methyl- neodecanamide (MNDA), a pyrethroid not used for insect control such as ⁇ (+/-)-3-allyl- 2-methyl-4-oxocyclopent-2-
  • DEET diethyl-meta-toluamide
  • DEPA N,N- diethylphenylacetamide
  • MNDA Methyl- neodecanamide
  • MNDA Methyl- neodecanamide
  • a pyrethroid not used for insect control such as ⁇
  • (+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1 ), (-)-l -epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella).
  • Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and diethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.
  • vinyl esters of aliphatic acids such as such as vinyl acetate and vinyl versatate
  • acrylic and methacrylic esters of alcohols such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate
  • mono- and diethylenically unsaturated hydrocarbons such as styrene
  • aliphatic diens such as butadiene.
  • the impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the active compounds of the present invention or spraying them onto the nets.
  • seed treatment refers to all methods that bring seeds and the compounds of the present invention into contact with each other
  • seed dressing to methods of seed treatment which provide the seeds with an amount of the compounds of the present invention, i.e. which generate a seed comprising a compound of the present invention.
  • the treatment can be applied to the seed at any time from the harvest of the seed to the sowing of the seed.
  • the seed can be treated immediately before, or during, the planting of the seed, for example using the "planter's box” method.
  • the treatment may also be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed.
  • the treatment is applied to unsown seed.
  • unsown seed is meant to include seed at any period from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant.
  • a procedure is followed in the treatment in which the seed is mixed, in a suitable device, for example a mixing device for solid or solid/liquid mixing partners, with the desired amount of seed treatment formulations, either as such or after previous dilution with water, until the composition is distributed uniformly on the seed. If appropriate, this is followed by a drying step.
  • a suitable device for example a mixing device for solid or solid/liquid mixing partners
  • the desired amount of seed treatment formulations either as such or after previous dilution with water, until the composition is distributed uniformly on the seed.
  • a drying step is followed.
  • the compounds of the present invention are in particular also suitable for being used for combating parasites in and on animals.
  • a further object of the present invention is therefore also to provide new methods for controlling parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. An another object of the invention is to provide pesticides for animals, which provide a long residual control of the parasites.
  • the invention also relates to compositions containing a parasiticidally effective amount of the compounds of the present invention and an acceptable carrier, for combating parasites in and on animals.
  • the present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of compounds of the present invention and an acceptable carrier or a composition comprising it.
  • the present invention also provides a non-therapeutic method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises applying to a locus-P a parasiticidally effective amount of a compound of the present invention and an acceptable carrier or a composition comprising it.
  • the invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises including a parasiticidally effective amount of a compound of the present invention and an acceptable carrier or a composition comprising it.
  • the invention relates further to the use of compounds of formulae I or II for treating, controlling, preventing or protecting animals against infestation or infection by parasites.
  • the invention relates also to the use of a compound of the present invention and an acceptable carrier or a composition comprising it, for the manufacture of a medicament for the therapeutic treatment of animals against infections or infestions by parasites.
  • compounds of the present invention are suitable for combating endo- and ectoparasites in and on animals.
  • the compounds of the present invention and compositions comprising them are suitable for systemic and/or non- systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.
  • Compounds of the present invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.
  • mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer
  • fur-bearing animals such as mink, chinchilla and raccoon, birds
  • Compounds of the present invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.
  • Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chig- gers, gnats, mosquitoes and fleas.
  • the compounds of the present invention are especially useful for combating ectoparasites.
  • the compounds of the present invention are especially useful for combating endopara- sites.
  • the compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively: fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus, cockroaches (Blattaria - Blattodea), e.g.
  • Blattella germanica Blattella asahinae, Pe- riplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuliggi- nosa, Periplaneta australasiae, and Blatta orientalis, flies, mosquitoes (Diptera), e.g.
  • Pediculus humanus capitis Pediculus humanus corporis, Pthi- rus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g.
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp,
  • Bots Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus,
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp, Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp,
  • Trichinosis Trichosyringida
  • Trichinellidae Trichinella spp.
  • Trichuridae Trichuris spp.
  • Capillaria spp Trichinosis
  • Rhabditida e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,
  • Strongylida e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunosto- mum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oe- sophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stepha- nurus dentatus , Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp.,
  • Spirurida e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Hab- ronema spp.,
  • Thorny headed worms e.g. Acanthocephalus spp., Macracantho- rhynchus hirudinaceus and Oncicola spp,
  • Planarians (Plathelminthes):
  • Flukes e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicro- coelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilhar- zia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp,
  • Cercomeromorpha in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.
  • the compounds of the present invention and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida. Moreover, the use of the compounds of the present invention and compositions containing them for combating mosquitoes is especially preferred.
  • the compounds of the present invention and compositions containing them also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).
  • the compounds of the present invention and compositions containing them can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits).
  • the present invention relates to the therapeutic and the non-therapeutic use of compounds of the present invention and compositions containing them for controlling and/or combating parasites in and/or on animals.
  • the compounds of the present invention and compositions containing them may be used to protect the animals from attack or infestation by parasites by contacting them with a parasitically effective amount of compounds of the present invention and compositions containing them.
  • contacting includes both direct contact (applying the pesticidal mixtures/compositions containing the compounds of the present invention directly on the parasite, which may include an indirect contact at it's locus-P, and optionally also administrating the pesticidal mixtures/composition directly on the animal to be protected) and indirect contact (applying the compounds/compositions to the locus of the parasite).
  • the contact of the parasite through application to its locus is an example of a non-therapeutic use of compounds of the present invention.
  • Locus-P as used above means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.
  • the compounds of the invention can also be applied preventively to places at which occurrence of the pests or parasites are expected.
  • the compounds of the present invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits).
  • Administration can be carried out prophylactically, therapeutically or non- therapeutically.
  • Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.
  • parasiticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the parasiticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a parasiticidally effective amount of the compositions will also vary according to the prevailing condi- tions such as desired parasiticidal effect and duration, target species, mode of application, and the like. Generally it is favorable to apply the compounds of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.
  • the compounds of the present invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and cap- sules.
  • the compounds of the present invention may be administered to the animals in their drinking water.
  • the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of a compound of the present invention, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
  • the compounds of the present invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection.
  • the compounds of the present invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection.
  • the com- pounds of the present invention may be formulated into an implant for subcutaneous administration.
  • the compounds of the present invention may be transdermal ⁇ administered to animals.
  • the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compounds of the present invention.
  • the compounds of the present invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions.
  • dips and sprays usually contain 0.5 ppm to 5,000 ppm and pref- erably 1 ppm to 3,000 ppm of the compounds of the present invention.
  • the compounds of the present invention may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
  • Suitable preparations are:
  • Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;
  • Emulsions and suspensions for oral or dermal administration for oral or dermal administration; semi-solid preparations; Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;
  • Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
  • Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.
  • Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methylpyrrolidone, 2-pyrrolidone, and mixtures thereof.
  • the active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
  • Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation.
  • examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.
  • Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.
  • Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.
  • Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.
  • Solutions for use on the skin are prepared according to the state of the art and accord- ing to what is described above for injection solutions, sterile procedures not being necessary.
  • solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, me- thylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylforma- mide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.
  • alkyleneglycol alkylether e.g. dipropylenglycol monomethylether
  • ketons such as acetone, me- thylethylketone
  • aromatic hydrocarbons such as acetone, me- thylethylketone
  • vegetable and synthetic oils dimethylforma- mide, dimethylacetamide, transcutol, solketal, propylencarbonate,
  • thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.
  • Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointmentlike consistency results.
  • the thickeners employed are the thickeners given above. Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.
  • pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.
  • Suitable solvents are: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyetha- nol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as al- kylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-alkylpyrrolidones such as N-methylpyrrolidone, N-butylpyrrolidone or N-octylpyrrolidone, 2-pyrrolidone, 2,2-
  • Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.
  • Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.
  • Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.
  • Suitable light stabilizers are, for example, novantisolic acid.
  • Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacry- lates, natural polymers such as alginates, gelatin.
  • Emulsions can be administered orally, dermally or as injections.
  • Emulsions are either of the water-in-oil type or of the oil-in-water type.
  • Suitable hydrophobic phases (oils) are:
  • liquid paraffins silicone oils, natural vegetable oils such as sesame oil, almond oil, cas- tor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C8-C12 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the Cs-Cio fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C16-C18, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C12-C18, isopropyl stearate,
  • 2-octyldodecanol cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof.
  • Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.
  • Suitable emulsifiers are:
  • non-ionic surfactants e.g. polyethoxylated castor oil, polyethoxylated sorbitan monoo- leate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether; ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin; anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt; cation-active surfactants, such as cetyltrimethylammonium chloride.
  • ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin
  • anionic surfactants such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono
  • Suitable further auxiliaries are: substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.
  • Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting sub- stances, preservatives, antioxidants, light stabilizers.
  • auxiliaries such as wetting agents, colorants, bioabsorption-promoting sub- stances, preservatives, antioxidants, light stabilizers.
  • Liquid suspending agents are all homogeneous solvents and solvent mixtures.
  • Suitable wetting agents are the emulsifiers given above.
  • Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.
  • the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.
  • suitable excipients are all physiologically tolerable solid inert substances.
  • Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates.
  • Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.
  • Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.
  • auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.
  • lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.
  • parasiticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the parasiticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a parasiticidally effective amount of the compositions will also vary according to the prevailing condi- tions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
  • compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the present invention.
  • the compounds of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.
  • Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 % by weight, preferably from 0.1 to 65 % by weight, more preferably from 1 to 50 % by weight, most preferably from 5 to 40 percent by weight.
  • Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 percent by weight, preferably of 1 to 50 percent by weight.
  • the preparations comprise the compounds of the present invention against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 percent by weight, very particularly preferably of 0.005 to 0.25 percent by weight.
  • the compositions comprising the compounds of the present invention are applied dermally / topically.
  • the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
  • solid formulations which release compounds of the present invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.
  • thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used.
  • Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of the present invention.
  • a detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075.
  • the active compounds can be applied solely or in a mixture with synergists or with other active compounds which act against pathogenic endo- and ectoparasites.
  • the active compounds of the present invention can be applied in mixtures with synthetic coccidiosis compounds, polyetherantibiotics as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin or with other pesticides which are described in the list M below.
  • synthetic coccidiosis compounds polyetherantibiotics as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin or with other pesticides which are described in the list M below.
  • compositions to be used according to this invention may also contain other active in- gredients, for example other pesticides, insecticides, herbicides, fungicides, other pesticides, or bactericides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides.
  • active in- gredients for example other pesticides, insecticides, herbicides, fungicides, other pesticides, or bactericides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides.
  • fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides.
  • these additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately
  • agents can be admixed with the agents used according to the invention in a weight ratio of 1 :10 to 10:1 . Mixing the compounds of the present invention or the com- positions comprising them in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.
  • Organo(thio)phosphates compounds acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyri- fos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, fam- phur, fenamiphos, fenitrothion, fenthion, flupyrazophos, fosthiazate, heptenophos, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxy
  • Pyrethroid compounds acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyflu- thrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cyperme- thrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fen- valerate, fluc
  • Chloride channel activators abamectin, emamectin benzoate, milbemectin, le- pimectin;
  • METI I compounds fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufen- pyrad, tolfenpyrad, flufenerim, rotenone;
  • METI II and III compounds acequinocyl, fluacyprim, hydramethylnon;
  • Inhibitors of oxidative phosphorylation azocyclotin, cyhexatin, diafenthiuron, fen- butatin oxide, propargite, tetradifon;
  • Moulting disruptors cyromazine, chromafenozide, halofenozide, methoxy- fenozide, tebufenozide; M.13. Synergists: piperonyl butoxide, tribufos;
  • Lipid biosynthesis inhibitors spirodiclofen, spiromesifen, spirotetramat
  • M.20 Octapaminergic agonists: amitraz
  • M.21 Diamide-type Ryanodine receptor modulators - Phthalamides: flubendiamide; (R)-, (S)- 3- Chlor-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2 - tetrafluor-1 -(trifluormethyl)ethyl]phenyl ⁇ - N2-(1 -methyl-2-methylsulfonylethyl)phthalamid (M21 .1 );
  • Diamide-type Ryanodine receptor modulators - Anthranilamide compounds chloranthraniliprole, cyantraniliprole,
  • N'-(3,5-Dibromo-2- ⁇ [5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino ⁇ - benzoyl)-hydrazinecarboxylic acid methyl ester M23.10
  • N'-(3,5-Dibromo-2- ⁇ [5-bromo- 2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino ⁇ -benzoyl)-N'-methyl- hydrazinecarboxylic acid methyl ester M23.1 1
  • N'-(3,5-Dibromo-2- ⁇ [5-bromo-2-(3- chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino ⁇ -benzoyl)-N,N'-dimethyl- hydrazinecarboxylic acid methyl ester M23
  • the anthranilamides M23.1 to M23.6 have been described in WO 2008/72743 and WO 2008/72783, those M23.7 to M23.12 in WO 2007/043677.
  • the phthalamide M 21 .1 is known from WO 2007/101540.
  • the alkynylether compound M27.1 is described e.g. in JP 2006/131529.
  • Organic sulfur compounds have been described in WO 2007/060839.
  • the isoxazoline compounds M 22.1 to M 22.5 have been described in e.g. WO 2005/085216, WO 2007/079162 and WO 2007/026965.
  • the aminofuranone compounds M 26.1 to M 26.10 have been described eg. in WO
  • - Inhibitors of complex III at Q 0 site e.g. strobilurins: azoxystrobin, coumeth- oxy-strobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxy-strobin/flufenoxystrobin, fluoxastro-bin, kresoxim-methyl,
  • - inhibitors of complex II e. g. carboxamides: benodanil, bixafen, boscalid, car- boxin, fen-furam, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thif- luz-amide, N-(44rifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H- pyr-azole-4-carboxamide and N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5- fluoro-1 H-pyrazole-4-carboxamide;
  • complex II e. g. carboxamides: benodanil, bixafen, boscalid, car- boxin
  • respiration inhibitors e.g. complex I, uncouplers: diflumetorim; nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam; ferimzone; organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin; and silthiofam;
  • DM I fungicides triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexacona- zole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothio-conazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole; imidazoles: imazalil, pefurazoate, prochloraz, triflumizol
  • Delta14-reductase inhibitors aldimorph, dodemorph, dodemorph-acetate, fen- propimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
  • phenylamides or acyl amino acid fungicides benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;
  • tubulin inhibitors such as benzimidazoles, thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl; triazolopyrimidines: 5-chloro-7- (4-methyl-piperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]tri-azolo[1 ,5-a]pyrimidine
  • cell division inhibitors diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone, pyriofenone;
  • - methionine synthesis inhibitors anilino-pyrimidines: cyprodinil, mepanipyrim, pyrimethanil;
  • blasticidin-S blasticidin-S, kasugamycin, kasugamycin hydrochlo- ride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin
  • MAP / histidine kinase inhibitors fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
  • Lipid and membrane synthesis inhibitors - Phospholipid biosynthesis inhibitors: edifenphos, iprobenfos, pyrazophos, iso- prothiolane;
  • lipid peroxidation dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
  • phospholipid biosynthesis and cell wall deposition dimethomorph, flumorph, mandipropamid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and N-(1 - (1 -(4-cyano-phenyl)-ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
  • organochlorine compounds e.g. phthalimides, sulfamides, chloronitriles:
  • glucan synthesis validamycin, polyoxin B; melanin synthesis inhibi- tors: pyroquilon, tricyclazole, carpropamid, dicyclomet, fenoxanil;
  • the invertebrate pest i.e. arthropodes and nematodes, the plant, soil or water in which the plant is growing can be contacted with the compound(s) of the present invention or composition(s) containing them by any application method known in the art.
  • "contacting” includes both direct contact (applying the compounds/compositions directly on the invertebrate pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the invertebrate pest or plant).
  • invertebrate pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of the present invention.
  • “Locus” in general means a habitat, breeding ground, cultivated plants, plant propagation material (such as seed), soil, area, material or environment in which a pest or parasite is growing or may grow.
  • pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the compounds of the present invention and the compositions comprising said compounds can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
  • the compounds of are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywood, furniture, etc., wooden articles such as particle boards, half boards, etc.
  • the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.
  • the compounds of the present invention can also be applied preventively to places at which occurrence of the pests is expected.
  • the compounds of the present invention may also be used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of the present invention.
  • contacting the plant includes both direct contact (applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 20 g per 100 m 2 .
  • Customary application rates in the protection of materials are, for example, from 0.01 g to 1 ,000 g of active compound per m 2 treated material, desirably from 0.1 g to 50 g per m 2 .
  • Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 % by weight, preferably from 0.1 to 45 % by weight, and more preferably from 1 to 25 % by weight of at least one repellent and/or insecticide.
  • the typical content of active ingredient is from 0.001 % by weight to 15 % by weight, desirably from 0.001 % by weight to 5 % by weight of active compound.
  • the content of active ingredient is from 0.001 to 80 % by weight, preferably from 0.01 to 50 % by weight and most preferably from 0.01 to 15 % by weight.
  • the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4,000 g per hectare, desirably from 5 g to 600 g per hectare, more desirably from 10 g to 300 g per hectare.
  • the application rates of the active ingredients are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 1 kg per 100 kg of seed, in particular from 1 g to 250 g per 100 kg of seed, in particular from 10 g to 150 g per 100 kg of seed.
  • Example 6 lodomethane (0.73 g, 5.16 mmol) and A/,/V-diisopropylethylamine (0.44 g, 3.44 mmol) were added to a solution of compound 3 (0.5 g, 1 .72 mmol) in tetrahydrofuran (THF) (40 mL) and the resulting solution was heated to reflux for 2 hours. The solution was partitioned between saturated aqueous ammonium chloride (NH 4 CI) solution and ethyl acetate (EtOAc) and the organic phase was washed twice with water, dried over Na2S0 4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (silica gel, gradient of cyclohexane/EtOAc) to yield the desired sulfonimidamide 6 (0.46 g, 1.5 mmol, yield: 87%).
  • NH 4 CI saturated aqueous ammonium chloride
  • EtOAc ethy
  • Ethyl bromoacetate (0.26 g, 1 .54 mmol) and A/,/V-diisopropylethylamine (0.06 g, 0.46 mmol) were added to a solution of compound 4 (100 mg, 0.31 mmol, prepared from the corresponding cyano-sulfonimidamide in analogy to the preparation process described for compound 3) in TH F (40 mL).
  • the solution was heated to reflux for 2 hours, then partitioned between saturated aqueous NH 4 CI solution and EtOAc and the organic phase was washed twice with water, dried over Na2S0 4 and evaporated under reduced pressure. The residue was kept under high vaccum for 48 hours to yield the desired sulfonimidamide 10 (100 mg, 0.24 mmol, yield: 77%).
  • Trifluoroacetic acid anhydride (TFAA, 0.245 g, 1 .17 mmol) was added to a solution of cyano-sulfonimidamide 1 -1 (0.1 g, 0.39 mmol) in CH2CI2 (15 mL) and the solution was stirred at 20 °C for 16 hours. Volatiles were removed under reduced pressure and the residue was purified by flash column chromatography (silica gel, gradient of CH 2 CI 2 /MeOH) to yield the sulfonimidamide 14 (0.1 g, 0.31 mmol, yield: 78%).
  • a> # denotes the attachment point to the remainder of the molecule of formula l-c' or ll-c';
  • test solutions were prepared by dissolving the active compound at the desired concentration in a mixture of 1 :1 (v/v) distilled water / acteon. The test solutions were prepared at the day of use. The concentration of the test solution is indicated, if not specified otherwise, in weight per volume.
  • Green Peach Aphid (Myzus persicae)
  • Myzus persicae For evaluating control of green peach aphid (Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.
  • the compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications.
  • aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed.
  • the active compounds were formulated in 50:50 (vohvol) acetone : water and 100 ppm KineticaTM surfactant.
  • Cotton plants at the cotyledon stage (one plant per pot) were infested by placing a heavily infested leaf from the main colony on top of each cotyledon. The aphids were allowed to transfer to the host plant overnight, and the leaf used to transfer the aphids was removed. The cotyledons were dipped in the test solution and allowed to dry. After 5 days, mortality counts were made.
  • test unit For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 24- well-microtiter plates containing an insect diet and 20-30 A. grandis eggs.
  • the compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 20 ⁇ , using a custom built micro atomizer, at two replications.
  • microtiter plates were incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
  • Thrips potency of each compound was evaluated by using a floral-immersion technique.
  • Plastic petri dishes were used as test arenas. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry. Treated flowers were placed into individual petri dishes along with 10 - 15 adult thrips. The petri dishes were then covered with lids. All test arenas were held under continuous light and a temperature of about 28oC for duration of the assay. After 4 days, the numbers of live thrips were counted on each flower, and along inner walls of each petri dish. The level of thrips mortality was extrapolated from pre-treatment thrips numbers.
  • Rice seedlings were cleaned and washed 24 hours before spraying.
  • the active compounds were formulated in 50:50 acetone:water (vohvol), and 0.1 % vol/vol surfactant (EL 620) was added.
  • Potted rice seedlings were sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants were kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality was recorded after 72 hours.

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention porte sur un procédé pour la lutte contre les animaux nuisibles invertébrés, en particulier des insectes, des animaux nuisibles arthropodes et des nématodes, à l'aide de composés de formule (I) ou (II) et des sels de ceux-ci, des énantiomères de ceux-ci et des diastéréoisomères de ceux-ci, (I), (II). Dans les formules, Het représente un hétérocycle à 5 ou 6 chaînons lié par C ou lié par N ; n représente 0, 1 ou 2 ; R1 et R2, s'ils sont présents, représentent chacun H, un atome d'halogène ou un groupe alkyle en C1-C4, halogénoalkyle en C1-C4, alcényle en C2-C4, alcynyle en C2-C4 et similaire ; R3 représente H ou un groupe alkyle en C1-C4, halogénoalkyle en C1-C4, cycloalkyle en C3-C6 et similaire ; R4 représente un groupe alkyle en C1-C4, halogénoalkyle en C1-C4, cycloalkyle en C3-C6 et similaire ou en variante R3 et R4 forment ensemble une fraction alcanediyle en C2-C4 éventuellement substituée et similaire ; A représente de préférence SR6 ou NR7R8, R6 représentant un groupe alkyle en C1-C4, halogénoalkyle en C1-C4, alcényle en C2-C4, alcynyle en C2-C4, benzyle, 1,3-dioxolan-2-yl(alkyle en C1-C6) et similaire, R7 représentant H ou un groupe alkyle en C1-C4, halogénoalkyle en C1-C4, cycloalkyle en C3-C6 et similaire et R8 représentant H ou un groupe alkyle en C1-C4 et similaire ; B représente de préférence S ou NR10, R10 représentant H ou un groupe alkyle en C1-C4, halogénoalkyle en C1-C4 et similaire ; ou en variante R10 et l'un de R6, R7 ou R8 pouvant former ensemble une fraction alcanediyle en C2-C3 éventuellement substituée dans laquelle un atome de carbone peut être remplacé par un groupe carbonyle. La présente invention porte en outre sur un procédé pour la protection de semences et/ou des plantes qui se développent à partir de celles-ci, sur un matériel de propagation des végétaux, sur un procédé pour la protection d'un animal d'une infestation ou un infection par des parasites, comprenant au moins un composé représenté par les formules (I) ou (II), leurs sels, énantiomères ou diastéréoisomères, et sur une composition agricole ou vétérinaire contenant au moins un composé représenté par les formules (I) ou (II), leurs sels, énantiomères ou diastéréoisomères.
PCT/EP2011/073586 2010-12-22 2011-12-21 Composés sulfoximinamides servant à lutter contre des animaux nuisibles invertébrés ii WO2012085081A1 (fr)

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN108271461A (zh) * 2018-01-19 2018-07-13 新疆天业（集团）有限公司 一种莲藕种子的处理方法

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Publication number Priority date Publication date Assignee Title
CN108271461A (zh) * 2018-01-19 2018-07-13 新疆天业（集团）有限公司 一种莲藕种子的处理方法

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