WO2018166855A1 - Dihydroisoxazoles à substitution hétérobicyclique - Google Patents

Dihydroisoxazoles à substitution hétérobicyclique Download PDF

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WO2018166855A1
WO2018166855A1 PCT/EP2018/055539 EP2018055539W WO2018166855A1 WO 2018166855 A1 WO2018166855 A1 WO 2018166855A1 EP 2018055539 W EP2018055539 W EP 2018055539W WO 2018166855 A1 WO2018166855 A1 WO 2018166855A1
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compounds
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alkyl
methyl
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Arun Narine
Karsten Koerber
Martin John MCLAUGHLIN
Birgit GOCKEL
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the invention relates to compounds of formula I,
  • B 2 and B 3 are independently of each other N and CR B , with the proviso that at most one of B 1 , B 2 and B 3 is N;
  • R B is H, CI, F, Br, CF 3 , or OCF 3 ;
  • Y is taken together with the carbon atom of CR 2 and the C 2 and C 3 -atoms of the adjacent X 1 containing ring to form a 5- to 7-membered saturated or partially unsaturated carbo- or heterocycle where the heterocycle contains 1 to 3 heteroatoms selected from N, O, or S;
  • R a and R independently of each other, are H, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-halo- alkoxy, Ci-C 6 -alkyl-S(0)m-Ci-C 6 -alkyl, Ci-C 6 -alkyl-S(0)m-Ci-C 3 -haloalkyl, C 3 -C 6 - cycloalkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, C 2 -C6-alkenyloxy, C 2 -C6-alkynyloxy, S(0) m - Ci-C6-alkyl, S(0) m -Ci-C6-haloalkyl, which groups are unsubstituted or substituted by one or more R c ;
  • R c is halogen, CN, CrC 4 -alkyl, or CrC 4 -haloalkyl
  • n 0, 1 , or 2;
  • R 1a is H, halogen, Ci-C 4 -alkyl, or Ci-C 4 -haloalkyl;
  • n 1 , 2, 3, or 4;
  • # is a direct bond, or together with CR 2 and NR 3 forms an azetidine ring;
  • R 2 is H, halogen, CN, N0 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalk- oxy, Ca-Ce-cycloalkyl, OR a , NR a R b , N0 2 ; and
  • R 3 is a group as defined for R a ;
  • R 4 is a group as defined for R a ; or Ci-C 6 -alkyl-S(0)m-Ci-C 6 -alkyl, Ci-C 6 -alkyl-S(0)m-Ci-C 3 -ha- loalkyl, C3-C6-cycloalkyl-Ci-C 4 -alkyl, 3- to 7-membered heterocyclyl bonded directly or via Ci-C4-alkylene spacer, which heterocycles contain 1 to 3 heteroatoms selected from N, O, or S, wherein S-atoms as ring members are present as S, SO, or S0 2 ; and which R 4 groups are unsubstituted or substituted by one or more R c ; and
  • R 5 independently of each other, are H, halogen, or OH;
  • the invention relates to processes and intermediates for preparing the compounds of formula I, and also to active compound combinations, and compositions comprising them, and to their use for protecting growing plants from attack or infestation by invertebrate pests. Furthermore, the invention relates to methods of applying such compounds. The invention also relates to seed comprising such compounds.
  • Invertebrate pests and in particular 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.
  • There is an ongoing need for new agents for combating invertebrate pests such as insects, arachnids and nematodes.
  • W010/070068, W01 1/157748, W012/107533, WO 12/120135, WO 12/158396, and WO 16/077158 describe dihydroisoxazoles with heterocyclic substituents. These compounds are mentioned to be useful for combating invertebrate pests.
  • the compounds of the formula I can be prepared by the methods as described below or and in the synthesis descriptions of the working examples, or by standard methods of organic chemistry.
  • the substituents, variables and indices are as defined above for formula I, if not otherwise specified.
  • Compounds la that is compounds of formula I wherein R 5b is hydrogen, can be prepared by reacting compounds of formula lla in an imination/Michael addition reaction with hydroxylamine, as shown below in Scheme .
  • Suitable reaction conditions are described in WO2012/158396 and WO2015/128358.
  • hydroxylamine is used as the hydrochloride salt.
  • the reaction is generally carried out in the presence of a base such as, NaOH, KOH, Na2C03.
  • Suitable solvents are aqueous, such as water or mixtures of water with polar organic solvents, such as tetrahydrofuran (THF), dioxane and lower alkanols.
  • compounds of formula lla can be prepared in analogy to reports in literature such as, EP2172462 and WO2014/39489. by means of an aldol condensation reaction between compounds of formula Ilia and compounds of formula IVa.
  • Compounds of formula IVa are commercially available, or can be made by standard methods which are described in literature, such as WO2010/125130 and WO2014/206911 , and known to a person skilled in the art.
  • compounds of formula la can be prepared in a 1 ,3-dipolar cycloaddition between styrene compounds of formula IVb and nitrile oxides derived from aldoximes of formula Illb wherein Z is hydrogen, as outlined below in Scheme 2.
  • the reaction typically proceeds through the intermediacy of in situ generated hydroxamic acid halogenides, usually chloride, by reaction with chlorine, hypochlorite, N-chlorosuccinimide (“NCS”), or chloramine-T.
  • the halogenating agent is combined with the aldoxime before addition, or in the presence of styrene compound IVb.
  • reaction can be run in a wide variety of solvents including ⁇ , ⁇ -dimethylformamide (DMF), dichloromethane, chlorobenzene, toluene, acetonitrile, THF, ethyl acetate.
  • DMF ⁇ , ⁇ -dimethylformamide
  • Compounds of formula IVb are commercially available, or can be made by standard methods which are described in literature, such as WO2012/59441 , WO2008/150393 and WO2012/4326, and known to a person skilled in the art.
  • Aldoximes of formula Illb' that is compounds of formula Illb wherein Z is hydrogen, can be obtained by reacting aldehydes of formula Illc with hydroxylamine, preferably as its
  • hydrochloride salt The reactions are typically performed in the presence of solvents such as, lower alcohols, like methanol and ethanol, water, DMF, acetonitrile, or mixtures thereof.
  • solvents such as, lower alcohols, like methanol and ethanol, water, DMF, acetonitrile, or mixtures thereof.
  • a base can be employed in the reaction such as organic bases like triethylamine, pyridine, or sodium acetate, or inorganic bases such as NaOH or K2CO3.
  • R 5b is not hydrogen
  • compounds of formula la or la' that is compounds of formula I wherein both, R 5a and R 5 are hydrogen
  • a base such as lithium diisopropylamide, lithium hexamethyldisilazide, or the like
  • electrophile e.g.
  • a halogenating agent such as 4-iodotoluene difluoride, N- fluorobenzenesulfonimide (“NFSI”), N-chlorosuccinimide (“NCS”), N-bromosuccinimide (“NBS”), or N-iodosuccinimide (“NIS”)
  • an alkylating agent such as alkyl halide, e.g. methyl iodide
  • a sulfanylating agent such as methanesulfenyl chloride, S-methyl methanethiosulfonate or dimethyldisulfide, or, for introducing OH, a hydroxylating agent such as, e.g.
  • Compounds of formula 111 can be obtained by reacting a compound of formula llld with (chloromethylene)dimethyliminium chloride, which can either be obtained from commercial sources or generated in situ by treatment of DMF with an activating agent, usually
  • Typical solvents are dichloromethane, chloroform, 1 ,2-dichloroethane, DMF, and mixtures thereof.
  • compounds of formula II lc can be prepared by reacting coumpounds of formula I lie, wherein Q is a halogen, preferably I or Br, with carbon monoxide and a reducing agent in a formylation reaction. Suitable reaction conditions are described in WO2006/35954, WO2012/42006, and WO2010/72781.
  • the reaction is generally performed in the presence of a palladium catalyst such as, e.g.
  • Suitable reducing agents are, e.g., triethylsilane (EtaSiH), and sodium formate (HC0 2 Na).
  • Suitable solvents are DMF, ⁇ , ⁇ -dimethylacetamide (DMA), acetonitrile, 1- methyl-2-pyrrolidone, dimethylsulfoxide (DMSO).
  • a base can be employed in the reaction, such as Na2C03, triethylamine, ⁇ , ⁇ -diisopropylethylamine.
  • Compounds of formula llle can be prepared from compounds of formula llld in a halogenation reaction. Suitable reaction conditions are described in WO2010/141273 and US2003/236297.
  • the reaction is typically carried out by treating a comound of formula llld with a halogenating agent such as N-chloro- succinimide (“NCS”), sulfuryl chloride, N-bromosuccinimide (“NBS”), bromine, N-iodosuccin- imide (“NIS”), iodine, or the like.
  • a halogenating agent such as N-chloro- succinimide (“NCS"), sulfuryl chloride, N-bromosuccinimide (“NBS”), bromine, N-iodosuccin- imide (“NIS”), iodine, or the like.
  • Suitable solvents are chloroform, DMF, THF, and
  • an acid can be employed, such as Bronstedt acids like acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, or sulfuric acid, or Lewis acids such as aluminum chloride (AlC ), iron(lll) chloride (FeC ), iron(lll) bromide (FeBr3), or the like.
  • Bronstedt acids like acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, or sulfuric acid
  • Lewis acids such as aluminum chloride (AlC ), iron(lll) chloride (FeC ), iron(lll) bromide (FeBr3), or the like.
  • compounds of formula llle can be prepared from compounds of formula llle', wherein Q is NO 2 , by a sequence involving a reduction reaction to the corresponding amine followed by a Sandmeyer reaction. Suitable reaction conditions are described in the literature and are known to a person skilled in the art.
  • reaction is generally carried out in the presence of a Lewis acid activator such as AICI3, tin(IV) chloride (SnCU), FeC , borontrifluoride etherate (BF3-OEt2).
  • a Lewis acid activator such as AICI3, tin(IV) chloride (SnCU), FeC , borontrifluoride etherate (BF3-OEt2).
  • Suitable solvents are dichloromethane, chloroform, 1 ,2-dichloroethane, nitromethane, or the like.
  • compounds of formula Ilia can be prepared from compounds of formula llle, wherein Q is a halogen, preferably I or Br, by reacting it with the corresponding alkyl vinyl ether or enamine in a Heck reaction, followed by aqueous acid mediated hydrolysis.
  • Suitable reaction conditions are described in WO2014/206907, WO2010/7278, and A. Laksmikanta et al. Tetrahedron
  • the reaction is generally carried out in the presence of a palladium catalyst, such as
  • Suitable solvents are DMF, DMSO, THF, 1 -methyl-2- pyrrolidone, DMA, lower alkanols, water, or mixtures thereof.
  • the corresponding alkyl vinyl ethers are commercially available, or can be prepared by standard methods known to a person skilled in the art.
  • the corresponding enamines are generated in situ by combining the corresponding aldehyde with a secondary amine such as pyrrolidie.
  • Compounds of formula V that is compounds of formula llld wherein R 1 , R 2 , and R 3 are hydrogen and Y is a 5- or 6-membered carbocyclic ring, can be prepared by reacting compounds of formula VI with an acid chloride or the corresponding carboxylic acid in an amidation reaction, as shown below in Scheme 3.
  • the amidation reaction is preferably carried out with the acid chloride or, if the acid chloride is not commercially available, by prior transformation of the carboxylic acids with oxalyl chloride [(COCI)2] or thionylchloride (SOCI2) to the corresponding acid chlorides, followed by reaction with the amine of formula VI.
  • amidation is carried out in the presence of a coupling reagent.
  • Suitable coupling reagents are known and are, e.g. selected from carbodiimides, such as N,N-dicyclohexylcarbodiimide (“DCC”) and ⁇ , ⁇ -diisopropylcarbodiimide (“DCI”), benzotriazole derivatives such as 1- [Bis(dimethylamino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (“HATU”), 0-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (“HBTU”), and 1-[Bis(dimethylamino)methylen]-5-chlorobenzotriazolium 3-oxide hexafluorophosphate (“HCTU”), or phosphonium-derived activators, such as (Benzotriazol-1 - yloxy)tris(d
  • Compounds of formula VI can be obtained from coumpounds of formula VII by a reduction reaction.
  • the reactions are typically carried out under an atmosphere of molecular hydrogen, usually at a pressure between 1-30 bars, and in the presence of a metal catalyst such as palladium on activated carbon ("Pd/C"), Raney-nickel ("Ra-Ni”), platinum(IV) oxide (Pt02), platinum on activated carbon (“Pt/C).
  • a metal catalyst such as palladium on activated carbon (“Pd/C"), Raney-nickel (“Ra-Ni”), platinum(IV) oxide (Pt02), platinum on activated carbon (“Pt/C).
  • Suitable solvents include lower alcohols like methanol, ethanol, and isopropanol, and THF, dioxane, water, or mixtures thereof.
  • an acid can be employed in the reaction such as, e.g. hydrochloric acid, or acetic acid.
  • compounds of formula VII can be prepared by reacting compounds of formula VIII with hydroxylamine, preferably used as its hydrochloride salt.
  • Suitable reaction conditions can be found in US2003/114666.
  • the reactions are typically performed in the presence of solvents such as lower alcohols like methanol, and ethanol, and water, DMF, acetonitrile, or mixtures thereof.
  • a base can be employed in the reaction, such as e.g. organic bases like triethylamine, pyridine, sodium acetate, or inorganic bases such as NaOH, or K2CO3.
  • compounds of formula Xa, or Xb can be prepared by reacting compounds of formula IX in a Dieckmann reaction. Suitable reaction conditions are described in US2009/62318, US2005/85554, and WO2012/58065. The reaction is generally carried out in the presence of a base such as NaH, potassium tert-butylate, lithium diisopropyl amide, lithium hexamethyl- disilazide, sodium methanolate, sodium ethanolate. Suitable solvents are THF, toluene, or lower alkanols.
  • Compounds of formula IX can be prepared as described in US2006/3990, and Y.-K. Shue et al. Journal of Organic Chemistry 1991 , 56, 2936-2938.
  • Suitable solvents are THF, or the like.
  • Compounds of formula XVa are commercially available or can be made by methods known to a person skilled in the art.
  • Compounds of formula XIII or XI I ⁇ can be derived from compounds of formula XII and ⁇ , resp., by in situ activation of the primary alcohol, followed by nucleophilic substitution with the appropriate halogenide W.
  • the reaction is typically carried out by treatment of a solution of compounds of formula XII or ⁇ , resp., with an activating/chlorinating agent such as thionyl chloride (SOC ), oxalyl chloride [(COCI)2], phosphosous trichloride (PCI3), phosophorous pentachloride (PC ), or
  • an activating/chlorinating agent such as thionyl chloride (SOC ), oxalyl chloride [(COCI)2], phosphosous trichloride (PCI3), phosophorous pentachloride (PC ), or
  • Methanesulfonyl chloride (MeSC ⁇ CI).
  • Suitable solvents are dichloromethane, chloroform, DMF, DMA, benzene, tetrahydrofurane, or mixtures thereof.
  • a base such as triethylamine, ⁇ , ⁇ -diisopropylethylamine, pyridine, or the like, and/or a nucleophilic catalyst such as, e.g. 4- (N,N-dimethlamino)pyridine (“DMAP”) can be employed in the reaction.
  • the reaction is typically carried out by treatment of a solution of compound of formula XII or ⁇ , resp., with an activating/brominating agent such as a combination of CBr4/PP i3, or phosphorous tribromide (PBr 3 ).
  • an activating/brominating agent such as a combination of CBr4/PP i3, or phosphorous tribromide (PBr 3 ).
  • Suitable solvents are dichloromethane, THF, diethyl ether, DMF, benzene, or mixtures thereof.
  • a base can be employed in the reaction such as triethylamine, pyridine, or the like.
  • compounds of formula XII or XM' can be obtained from compounds of formula XI and ⁇ , respectively, wherein R 6 is an alkyl group or hydrogen by treatment with a reducing agent.
  • a reducing agent for compounds of formula XI or XI', respectively, wherein R 6 is an alkyl group, preferentially methyl, ethyl, or the like, suitable reaction conditions are described in WO2011/66183. The reaction is typically performed with diisobutylaluminum hydride (1-BU 2 AIH), or lithium aluminum hydride (L1AIH4) as the reducing agent, and at temperatures between -78°C and 20-25°C.
  • diisobutylaluminum hydride (1-BU 2 AIH)
  • L1AIH4 lithium aluminum hydride
  • Suitable solvents are, e.g. THF, diethyl ether, toluene, dichloromethane, hexanes, or mixtures thereof.
  • suitable reaction conditions are described in WO2012/33390.
  • the reaction is performed with borane tetrahydrofuran complex (BH3 THF), borane dimethylsulfide complex (BH3-SMe2), or lithium aluminum hydride (LiAIH 4 ) as the reducing agent and at temperatures between 0°C and 60°C.
  • Suitable solvents are THF, diethyl ether, or the like.
  • Compounds of formula Xla that is compounds of formula XI wherein X 1 is S, and R 6 is hydrogen, can be prepared as described in J.-M. Duffault et al. Synthetic Communiations 1998, 28, 2467-2481.
  • Suitable coupling reagents are well known and are selected from carbodi- imides, such as ⁇ , ⁇ -dicyclohexylcarbodiimide (“DCC”) and ⁇ , ⁇ -diisopropylcarbodiimide (“DCI”), benzotriazole derivatives such as 1 -[Bis(dimethylamino)methylene]-1 H-1 ,2,3-triazolo[4,5- b]pyridinium 3-oxid hexafluorophosphate (“HATU”), 0-(Benzotriazol-1-yl)-N,N,N',N'- tetramethyluronium hexafluorophosphate (“HBTU”) and 1-[Bis(dimethylamino)methyl
  • the reaction is generally carried out in the presence of a metal hydride reducing agent, usually lithium aluminum hydride (UAIH4).
  • a metal hydride reducing agent usually lithium aluminum hydride (UAIH4).
  • Suitable solvents are THF, diethyl ether, or the like.
  • Compounds of formula XVIIIa or XVIIIb can be prepared by reacting compounds of formula XVIIa or XVIIb, resp., with formaldehyde or a formaldehyde surrogate such as
  • reaction is generally carried out in the presence of a base such as N-benzyltrimetylammonium hydroxide, NaH, lithium
  • compounds of formula XVIIa or XVIIb can be prepared by reacting compounds of formula Villa, Vlllla', Vlllb, or Vlllb', resp., with para-toluenesulfonylmethyl isocyanide ("TosMIC") in a Van Leusen reaction. Suitable reaction conditions are described, e.g. in
  • WO201 1/69063 or in J. Froehlich et al. Journal fur Praktician Chemie (Leipzig), 1990, 332, 995-1003.
  • the reaction is generally carried out in the presence of a base such as potassium tert-butylate (KOtBu), or the like.
  • Suitable solvents are 1 ,2-dimethoxyethane, lower alkanols, DMSO, THF, or mixtures thereof.
  • Compounds of formula XVIIIc on the other hand, can be obtained from compounds of formula XVI lc by a chemoselective reduction reaction. Suitable reaction conditions can be found in EP2090570, WO2013/13308, and in F. F. Fleming et al. Journal of Organic Chemistry, 2005, 70, 3845-3849.
  • reaction is generally carried out in the presence of a hydride donor agent such as sodium tetrahydroborate (NaBH 4 ), lithium tetrahydroborate (L1BH4), calcium borohydride (Ca(BH 4 )2), or the like.
  • a hydride donor agent such as sodium tetrahydroborate (NaBH 4 ), lithium tetrahydroborate (L1BH4), calcium borohydride (Ca(BH 4 )2), or the like.
  • Suitable solvents are THF, lower alkanols, water, or mixtures thereof.
  • compounds of formula XVIIc can be prepared by reaction of compounds of formula XVIc with a cyanoacetate ester of formula XVb in a cyclization reaction. Suitable reaction conditions are described in US6689906, US6548498, and US2002/61874.
  • the reaction is generally carried out in the presence of a base such as sodium alkoxide, potassium alkoxide, Na2CC>3, K2CO3, NaH, or the like.
  • a base such as sodium alkoxide, potassium alkoxide, Na2CC>3, K2CO3, NaH, or the like.
  • Suitable solvents are DMF, lower alkanols, acetonitrile, DMSO, or the like.
  • Cyanoacetate esters of formula XVb are commercially available, or can be made by standard methods which are known to a person skilled in the art.
  • Compounds of formula XVIc, wherein X 1 is S, and W and W 2 are a halogen, usually CI or Br, can be prepared as described in T. Dey et al. Tetrahedron Lett. 2010, 51 , 2089-2091 , K. Hammer et al. Acta Chemica Scandinavica 1997, 51 , 392-402, and US2009/326187.
  • Compounds of formula XXV and XXV that is compounds of formula llld wherein R 1 is H, CR 2 -#-NR 3 forms an azetidine ring, W 3 is H, halogen or NO2, and Y is a 5-membered heterocyclic ring, can be prepared by reacting a compound of formula XXIV or XXIV, resp., wherein W 4 is halogen or alkoxy, in a nucleophilic substitution reaction. Suitable reaction conditions are described in WO2013/9517, US2003/229079, EP1216249, and US2008/71084.
  • the reaction is generally performed in the presence of a base such as K 2 C0 3 , NaH, Cs 2 C0 3 , lower alkoxides, or the like.
  • a base such as K 2 C0 3 , NaH, Cs 2 C0 3 , lower alkoxides, or the like.
  • Suitable solvents are DMF, DMSO, N-methyl-2-pyrrolidone, THF, lower alkanols, toluene, or the like.
  • a copper salt can be employed in the reaction such as, e.g. copper(l) iodide, copper(l) bromide, copper(ll) oxide, or the like.
  • compounds of formula XXIV or XXIV can be obtained by metallating compounds of formula XXIII and XXIII', respectively, wherein G is H, Br, or I, with a strong base or metallating agent and reacting it with compounds of formula XXII.
  • Suitable reaction conditions are described in US2004/19205, and WO201 1/69063.
  • Suitable strong bases and metallating agents, resp., are lithium diisopropylamine, butyllithium, iP ⁇ MgCI-LiCI ("TurboGrignard"), tert-butyllithium, magnesium, lithium tetramethylpiperidine.
  • Suitable solvents are THF, diethyl ether, toluene, hexanes, or the like, as well as mixtures thereof.
  • a Lewis acid activator can be employed in the reaction such as, e.g. BF3-OEt2, or Sc(OTf)3.
  • Compounds of formula XXII, XXIII and ⁇ are commercially available or can be prepared as described in the literature, or by standard methods which are known to a person skilled in the art.
  • compounds of formula llld' that is compounds of formula llld wherein R 1 , R 2 , and R 3 are hydrogen, Y is a 5- or 6-membered carbocyclic ring, and X 1 is O
  • Suitable reaction conditions are described in P. Alonso et al. Angew. Chem. 2015, 127, 15726-15730, A. Blanc et al. J. Org. Chem. 2009, 74, 5342-5348, M. Yoshida et al. Tetrahedron Letters 2008, 49, 5021-5023, and C.-Y. Lo et al. Journal of Organic Chemistry 2002, 67, 3930-3932.
  • Suitable ⁇ -acid catalysts are, e.g. cationic gold(l)-phosphine complexes, platinum(ll) salts, mercury(ll) salts, gold(lll) salts, and AgOTf/pTsOH.
  • compounds of formula XXVIII can be prepared by reacting compounds of formula XXVII', which are compounds of formula XXVII wherein R 8 is hydrogen, with a peroxicarboxylic acid, preferably meta-chloroperbenzoic acid, in a Prilezhaev reaction. Suitable reaction conditions are described in P. Alonso et al. Angew.
  • compounds of formula XXVII' can be prepared from a compound of formula XXVII, wherein R 8 is a silyl protecting group such as, e.g. trimethylsilyl, triethylsilyl, or the like, in a deprotection reaction. Suitable reaction conditions are described in P. Alonso et al. Angew. Chem. 2015, 127, 15726-15730, US2005/245530, and US2010/105700.
  • Compounds of formula XXVII can be prepared by reacting copmpounds of formula XXVI, wherein W 5 is OS(0)2CF3, Br, or I, with a mono-protected acetylene such as trimethylsilylacetylene, in a Sonogashira cross-coupling reaction. Suitable reaction conditions are described in P. Alonso et al. Angew. Chem. 2015, 127, 15726-15730, and US2005/245530.
  • the reaction is generally carried out in the presence of a palladium catalyst such as tetra- kis(triphenylphosphine)palladium, Dichlorobis(triphenylphosphine)palladium, or the like, a co- catalytic copper(l) salt such as copper iodide, and an amine base such as trimethylamine, diethylamine, piperidine, N,N-diisopropylamine, ⁇ , ⁇ -diisopropylethylamine, or the like.
  • a palladium catalyst such as tetra- kis(triphenylphosphine)palladium, Dichlorobis(triphenylphosphine)palladium, or the like
  • a co- catalytic copper(l) salt such as copper iodide
  • an amine base such as trimethylamine, diethylamine, piperidine, N,N-diisopropylamine, ⁇ , ⁇ -d
  • Other compounds of formula XXVI can be prepared from the corresponding ketones in analogy to the above examples by standard methods of organic chemistry, which are known ba a person skilled in the art.
  • the compounds of formula I including their stereoisomers, salts, and N-oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.
  • reaction mixtures are worked up in a customary manner, e.g. by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products.
  • Some of the intermediates and end products are obtained in the form of colourless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.
  • radicals attached to the backbone of formula I may contain one or more centers of chirality.
  • compounds of formula I are present in the form of different
  • the invention relates to every possible stereoisomer of the formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.
  • the compounds of formula I may be present in the form of different structural isomers depending on the position of substituents.
  • the invention relates to every possible structural isomer as indicated in the compounds of formula I, and mixtures thereof.
  • the compounds of formula I may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the invention relates to amorphous and crystalline compounds of formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the formula I are preferably veterinary and/or agriculturally acceptable salts, preferably agriculturally acceptable salts. They can be formed in a customary manner, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality.
  • Veterinary and/or agriculturally useful salts of the compounds of formula I encompass especially the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the pesticidal action of the compounds of formula I.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, 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 formula I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • N-oxide includes any compound of formula I which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n - Cm indicates in each case the possible number of carbon atoms in the group.
  • halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
  • alkyl as used herein and in the alkyl moieties of alkylamino, alkylcarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl and alkoxyalkyl denotes in each case a straight-chain or branched al- kyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, more preferably from 1 to 3 carbon atoms.
  • alkyl group examples include 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 -ethyl propyl, n-hexyl, 1 ,1-di- methylpropyl, 1 ,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methyl- pentyl, ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-tri
  • haloalkyl as used herein and in the haloalkyl moieties of haloalkylcarbonyl, halo- alkoxycarbonyl, haloalkylthio, haloalkylsulfonyl, haloalkylsulfinyl, haloalkoxy and
  • haloalkoxyalkyl 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 from 1 to 4 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- C3-haloalkyl or Ci-C 2 -haloalkyl, in particular from Ci-C 2 -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 which is bonded via an oxygen atom and has usually from 1 to 10 carbon atoms, fre- quently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms.
  • alkoxy group examples are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butyloxy, 2-butyloxy, iso-butyloxy, tert.-butyloxy, and the like.
  • alkoxyalkyl refers to alkyl usually comprising 1 to 10, frequently 1 to 4, preferably 1 to 2 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 4, preferably 1 or 2 carbon atoms as defined above. Examples are CH 2 OCH3, CH2-OC2H5, 2-(methoxy)ethyl, and 2-(ethoxy)ethyl.
  • haloalkoxy denotes in each case a straight-chain or branched alkoxy group having from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms.
  • Preferred haloalkoxy moieties include C1-C4- haloalkoxy, in particular Ci-C2-fluoroalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoro- methoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoro-ethoxy, 2,2dichloro-2-fluorethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and the like.
  • Ci-C2-fluoroalkoxy such as fluoromethoxy, difluoromethoxy, trifluoro- methoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy
  • alkylthio (alkylsulfanyl: S-alkyl)
  • haloalkylthio refers to an alkylthio group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
  • haloalkylsulfinyl refers to an alkylsulfinyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
  • haloalkylsulfonyl refers to an alkylsulfonyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
  • haloalkylcarbonyl refers to an alkylcarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
  • alkoxycarbonyl refers to an alkylcarbonyl group as defined above, which is bonded via an oxygen atom to the remainder of the molecule.
  • haloalkoxycarbonyl refers to an alkoxycarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine.
  • alkenyl denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, 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 refers to an alkenyl group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms.
  • alkynyl denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, preferably 2 to 4 carbon atoms, 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.
  • haloalkynyl refers to an alkynyl group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms.
  • cycloalkyl as used herein and in the cycloalkyl moieties of cycloalkoxy and cyclo- alkylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 or from 3 to 6 carbon atoms, such as cyclopropyl (C-C3H5), cyclobutyl (C-C4H7), cyclopentyl (c- C5H9), cyclohexyl (c-CeHu), cycloheptyl (C-C7H13), cyclooctyl (c-CsH-is), cyclononyl (C-C9H17) and cyclodecyl (C-C10H19), or cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • halocycloalkyl as used herein and in the halocycloalkyl moieties of halocycloalkoxy and halocycloalkylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 C atoms or 3 to 6 C 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 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3,3- tetrafluorocyclpropyl, 1 - and 2-chlorocyclopropyl, 1 ,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2- trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1-,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1 -,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5- dichlorocyclopentyl and the like.
  • cycloalkenyl as used herein and in the cycloalkenyl moieties of cycloalkenyloxy and cycloalkenylthio denotes in each case a monocyclic singly unsaturated non-aromatic radical having usually from 3 to 10, e.g. 3 or 4 or from 5 to 0 carbon atoms, preferably from 3- to 8 carbon atoms.
  • exemplary cycloalkenyl groups include cyclopropenyl, cycloheptenyl or cyclo- octenyl.
  • carrier or “carbocyclyl” includes in general a 3- to 12-membered, preferably a 3- to 8-membered or a 5- to 8-membered, more preferably a 5- or 6-membered mono-cyclic, non-aromatic ring comprising 3 to 12, preferably 3 to 8 or 5 to 8, more preferably 5 or 6 carbon atoms.
  • the term “carbocycle” covers cycloalkyl and cycloalkenyl groups as defined above.
  • heterocycle or “heterocyclyl” includes in general 3- to 12-membered, preferably 5- or 6-membered, in particular 6-membered monocyclic heterocyclic non-aromatic radicals.
  • the heterocyclic non-aromatic radicals usually comprise 1 , 2 or 3 heteroatoms selected from N, O and S as ring members, wherein S-atoms as ring members may be present as S, SO or SO2.
  • Examples of 5- or 6-membered heterocyclic radicals comprise saturated or unsaturated, non- aromatic heterocyclic rings, such as 2- and 3-azetidinyl, 2- and 3-oxetanyl, 2- and 3-thietanyl, 2- and 3-thietanyl-S-oxide(S-oxothietanyl), 2- and 3-thietanyl-S-dioxide(S-dioxothiethanyl), 2- and 3-pyrrolidinyl, 2- and 3-tetrahydrofuranyl, 1 ,3-dioxolan-2-yl, thiolan-2-yl, S-oxothiolan-2-yl, S-di- oxothiolan-2-yl, 4- and 5-oxazolidinyl, 1 ,3-dioxan-2-yl, 1- and 3-thiopyran-2-yl, S-oxothiopyranyl, and S-dioxothiopyranyl.
  • variables of the compounds of the formula I have the following meanings, these meanings, both on their own and in combination with one another, being particular embodiments of the compounds of the formula I.
  • One embodiment relates to compounds of formula I wherein X 1 is S.
  • Another embodiment relates to compounds of formula I wherein X 1 is O.
  • B 1 , B 2 , and B 3 denote CR B ; the B 1 to B 3 containnig ring is accordingly a phenyl group A with three substituents R 2 , being R Ba , R B , and R Bc , wherein the "+" denotes the bond to the dihydroisoxazole moiety:
  • Formula I compounds wherein the B 1 to B 3 containnig ring is a group A correspond accordingly to formula .
  • R Ba is preferably selected from F, CI, Br, CF 3 , and OCF 3 .
  • R Bb and R Bc are independently preferably selected from H, F, CI, Br, CF 3 , and OCF 3 .
  • each one of the following combinations of R Ba , R B and R Bc wherein each line of Table A denotes a substitution pattern "A" of the phenyl ring bearing the R Ba , R B and R Bc groups.
  • Groups A-8, A-9, and A-11 are more preferred patterns in formula I compounds.
  • A-9, and A-1 1 are particularly preferred.
  • R 1 is preferably H.
  • 5a and R 5b are preferably H.
  • Y is a carbocyclic ring, preferably a five- or six-membered saturated ring.
  • Y is a heterocyclic ring, preferably a saturated heterocyclic ring with one hetero atom, which particularly is oxygen.
  • this saturated heterocyclic ring is a five-membered ring.
  • this saturated heterocyclic ring is a six-membered ring.
  • the heteroatom in ring Y is bonded to C 3 of the thiophene ring.
  • the heterocycle Y is a 2,5-dihydrofuran.
  • the heteroatom in ring Y is bonded to C 2 of the thiophene ring.
  • formula I.A and I.B at least one of Y 1 and Y 2 is CHR 1 ; if only one of Y 1 and Y 2 is CHR 1 , the other position is oxygen.
  • Formula I.A compounds are particularly preferred.
  • the saturated heterocyclic ring Y is a six-membered ring.
  • Y is a six-membered saturated carbocyclic ring.
  • Y is a six-membered saturated heterocyclic ring.
  • fomula I # is a direct bond.
  • R 2 and R 3 are preferably H.
  • formula I # forms together with CR 2 and NR 3 an azetidine ri
  • formula I Y is a carbocycle, and # is a direct bond.
  • Formula 1.6 compounds are particularly preferred.
  • Y is a carbocycle, # is together with CR 2 and NR 3 an azetidine ring.
  • Y is a dihydrofuran, and # is together with CR 2 and NR 3 an azetidine rin
  • Formula 1.10 compounds are particularly preferred.
  • Y is a 3,6-dihydro-2H-pyran, and # is together with CR 2 and NR 3 an azetidine ring.
  • Such preferred embodiments of formula I are the following:
  • Formula 1.14 compounds are particularly preferred .
  • R 4 is preferably selected from Ci-C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - cycloalkyl-Ci-C 2 -alkyl, Ci-C 2 -haloalkyl, Ci-C 2 -alkoxy-Ci-C 2 -alkyl, Ci-C 2 -haloalkoxy-Ci-C 2 -alkyl, CH 2 S(0) m -Ci-C4-alkyl, and CH 2 S(0)m-Ci-C 2 -haloalkyl, or 3-to 6-membered saturated heterocycles with 1 or 2 heteroatoms selected from O and S, wherein S-atoms as ring members may be present as S, SO, or S0 2 .
  • R 4 is particularly selected from CH 3 , C2H5, CH2CH2CH3, CH2CF3, C-C3H5, I -CN-C-C3H4, CH2SCH3, CH 2 S(0)CH 3 , CH 2 S(0) 2 CH 3 , and CH 2 S(0)2C 2 H5.
  • R 4 is selected from cyclopropyl-Ci-C 2 -alkyl, and 3- to 6-membered heterocyclyl, which rings are bonded directly or via a CrC 2 -alkylene spacer.
  • X 1 is O, or S
  • B 1 , B 2 and B 3 are independently of each other N and CR B , with the proviso that at most one of B 1 , B 2 and B 3 is N ;
  • R B is H , CI, F, Br, CF 3 , or OCF 3 ;
  • Y is taken together with the carbon atom of CR 2 and the C 2 and C 3 -atoms of the adjacent X 1 containing ring to form a 5- to 7-membered saturated or partially unsaturated carbo- or heterocycle where the heterocycle contains 1 to 3 heteroatoms selected from N, O, or S;
  • R a and R b independently of each other, are H, Ci-C6-alkyl , Ci-C6-alkoxy, Ci-C6-alkyl- S(0)m-Ci-C 6 -alkyl, Ci-C6-alkyl-S(0) m -Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 - alkenyl , C 2 -C 6 -alkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyloxy, C 5 -Ci 4 -cycloalkyl, which groups are unsubstituted or substituted by one or more R c ;
  • R c is halogen, cyano, Ci-C4-alkyl, or Ci-C4-haloalkyl
  • n 0, 1 , or 2;
  • # is a direct bond, or together with CR 2 and NR 3 forms an azetidine ring;
  • R 2 is H , halogen, CN , N0 2 , Ci-C 6 -alkyl , Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -haloalk- oxy, C 3 -C 6 -cycloalkyl, OR a , NR a R b , N0 2 ; and
  • R 3 is group as defined for R a ;
  • R 4 is a group as defined for R a ;
  • R 5a and R 5 independently of each other, are H, halogen, or OH ;
  • Table 1 Compounds of formula 1.11 in which R 1 is H, and the combination of A and R 4 for a compound corresponds in each case to one row of Table R
  • R-2 A-1 1 CH 3
  • R-8 A-1 1 CH2CF3
  • R-6 A-1 1 CH2CH2CH3
  • R-12 A-1 1 CH2OCH2CH3
  • the term "compound(s) of the invention” or “compound(s) according to the invention” refers to the compound(s) of formula (I) as defined above, which are also referred to as “compound(s) of formula I” or “compound(s) I” or “formula I compound(s)”, and includes their salts, tautomers, stereoisomers, and N-oxides.
  • the invention also relates to a mixture of at least one compound of the invention with at least one mixing partner as defined herein after.
  • Preferred weight ratios for such binary mixtures are from 5000: 1 to 1 :5000, preferably from
  • components I and II may be used in equal amounts, or an excess of component I , or an excess of component II may be used.
  • Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like.
  • Preferred mixing partners are insecticides, nematicides and fungicides.
  • the following list M of pesticides, grouped and numbered according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the invention can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation: M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1A carbamates, e.g.
  • IRAC Insecticide Resistance Action Committee
  • aldicarb aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of M.1 B organophosphates, e.g.
  • GABA-gated chloride channel antagonists such as: M.2A cyclodiene organochlorine compounds, as e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as e.g.
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox,
  • M.4 Nicotinic acetylcholine receptor agonists from the class of M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.2: (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2- pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8- nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; or from the class M.4B nicotine;
  • nAChR Nicotinic acetylcholine receptor agonists
  • M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g.
  • abamectin emamectin benzoate, ivermectin, lepimectin or milbemectin;
  • M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen; M.8 miscellaneous non-specific (multi-site) inhibitors, e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, or M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;
  • M.8A alkyl halides as methyl bromide and other alkyl halides
  • M.8B chloropicrin or M.8C sulfuryl fluoride
  • M.8D borax or M.8E tartar emetic
  • M.9 Selective homopteran feeding blockers, e.g. M.9B pymetrozine, or M.9C flonicamid;
  • M.10 Mite growth inhibitors e.g. M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;
  • M.11 Microbial disruptors of insect midgut membranes e.g. bacillus thuringiens!s or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;
  • M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetrad if on;
  • chlorfenapyr DNOC or sulfluramid
  • Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
  • M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas, e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;
  • benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;
  • M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide,
  • Octopamin receptor agonists e.g. amitraz
  • M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M.20B acequinocyl, or M.20C fluacrypyrim;
  • M.21 Mitochondrial complex I electron transport inhibitors e.g. M.21A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, or M.21 B rotenone;
  • M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B
  • M.22B. 2-[2-(4-Cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide, or M.22B.2: N-(3-Chloro-2-methylphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;
  • M.23 Inhibitors of the of acetyl CoA carboxylase such as Tetronic and Tetramic acid derivatives, e.g. spirodiclofen, spiromesifen, or spirotetramat;
  • M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, or M.24B cyanide;
  • Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen, or cyflumetofen;
  • M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chloran- traniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), tetraniliprole, or M.28.1 : (R)-3-Chlor-N1 - ⁇ 2-methyl-4-[1 ,2,2,2 -tetrafluor-1-(trifluormethyl)ethyl]phenyl ⁇ -N2-(1 -methyl-2-methylsulfonyl- ethyl)phthalamid and M.28.2: (S)-3-Chlor-N 1- ⁇ 2-methyl-4-[1 ,2,2,2 -tetrafluor-1- (trifluormethyl)ethyl]phenyl ⁇ -N2-(1 -methyl-2-methylsulfonylethyl)phthalamid, M.28.3:
  • cyclaniliprole M.28.4: methyl-2-[3,5-dibromo-2-( ⁇ [3-bromo-1-(3-chlorpyridin-2-yl)-1 H-pyrazol-5- yl]carbonyl ⁇ amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; M.28.5a) to M.28.5d) and
  • insecticidal active compounds of unknown or uncertain mode of action e.g. afidopyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide,
  • M.29.4 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one
  • M.29.5 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); or
  • M.29.6a E/Z-N-[1-[(6- chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide
  • M.29.6b E/Z)-N-[1-[(6-chloro- 5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide
  • M.29.6c E/Z)-2,2,2-trifluo- ro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide
  • M.29.6d E/Z)-N-[1 -[(6-bromo-3- pyridyl)methyl]-2-pyridyliden
  • M.29.8 fluazaindolizine
  • M.29.9.a) 4-[5-(3,5-dichlorop enyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1- oxothietan-3-yl)benzamide
  • M.29.11 a compound selected from M.29.11 , consisting of M.29.11 b) to M.29.11 p): M.29.11.b) 3- (benzoylmethylamino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]-6-
  • M.29.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.29.16b) 1- (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16c) N,5- dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide; M.29.16d) 1 - [1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
  • M.29.16e N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.29.16 ⁇ 1-(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.29.16g 1-[1-(1 -cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole- 4-carboxamide
  • M.29.16h N-methyl-1-(2-fluoro-1 -methyl-propyl]-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
  • M.29.16i) 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyrida
  • M.29.17 consisting of M.29.17a) to M.29.17j): M.29.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H- indazole-4-carboxamide; M.29.
  • M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456
  • M.4A.2 guadipyr is known from WO2013/003977
  • M.4A.3 (approved as paichongding in China) is known from WO2007/101369.
  • M.22B.1 is described in CN10171577 and M.22B.2 in CN102126994.
  • M.28.1 and M.28.2 are known from WO2007/101540.
  • M.28.3 is described in WO2005/077934.
  • M.28.4 is described in WO2007/043677.
  • M.28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO2013/024010, ⁇ .28.5 ⁇ ) is described in
  • M.29.3 is known from WO2006/089633 and M.29.4 from WO2008/06791 1.
  • M.29.5 is described in WO2006/043635, and biological control agents on the basis of bacillus firmus are described in WO2009/124707.
  • Compounds M.29.6a) to ⁇ .29.6 ⁇ ) are described in WO2012/029672, and M.29.6j) and M.29.6k) in WO2013/129688.
  • M.29.8 is known from WO2013/055584.
  • M.29.9.a) is described in
  • WO2010/060379 Broflanilide and M.29.1 1 .b) to M.29.1 1.h) are described in WO2010/018714, and M.29.1 1 i) to M.29.1 1 .p) in WO2010/127926. M.29.12.a) to M.29.12.c) are known from WO2010/006713, M.29.12.d) and ⁇ .29.12. ⁇ ) are known from WO2012/000896, and M.29.12. ⁇ ) to M.29.12.m) from WO2010/129497. M.29.14a) and M.29.14b) are known from WO2010/129497. M.29.14a) and M.29.14b) are known from
  • M.29.16.a) to M.29.16h) are described in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and ⁇ .29.16 ⁇ ) and M.29.16j) are described in WO2015/055497.
  • M.29.17a) to M.29.17J) are described in WO2015/038503.
  • M.29.18a) to M.29.18d) are described in US2014/0213448.
  • M.29.19 is described in W02014/036056.
  • M.29.20 is known from WO2014/090918.
  • Inhibitors of complex III at Q 0 site e. g. strobilurins: azoxystrobin (A.1 .1 ), coumethoxy- strobin (A.1 .2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenamin- strobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), mandestrobin (A.1 .10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1 .12), picoxy.strobin (A.1 .13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystro- bin (
  • inhibitors of complex III at Qi site cyazofamid (A.2.1 ), amisulbrom (A.2.2), [(3S,6S,7R,8R)- 8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-met yl-4,9-dioxo-1 ,5-dioxonan- 7-yl] 2-methylpropanoate (A.2.3), [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy- pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.4), [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycar onyloxy-4-methoxy-pyridine
  • inhibitors of complex II e. g. carboxamides: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18), N-(4'-trifluoromethylthiobiphenyl-2-yl)-3-di- fluoromethyl-1 -methyl-1 H-pyrazo
  • respiration inhibitors e. g. complex I, uncouplers: diflumetorim (A.4.1 ), (5,8-difluoro- quinazolin-4-yl)- ⁇ 2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl ⁇ -amine (A.4.2); nitrophenyl derivates: binapacryl (A.4.3), dinobuton (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferimzone (A.4.7); organometal compounds: fentin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); and silthiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides)
  • SBI fungicides Sterol biosynthesis inhibitors
  • C14 demethylase inhibitors (DMI fungicides): triazoles: azaconazole (B.1 .1 ), bitertanol (B.1 .2), bromuconazole (B.1 .3), cyproconazole (B.1 .4), difenoconazole (B.1.5), diniconazole (B.1 .6), diniconazole-M (B.1 .7), epoxiconazole (B.1 .8), fenbuconazole (B.1.9), fluquinconazole (B.1 .10), flusilazole (B.1.1 1 ), flutriafol (B.1.12), hexaconazole (B.1 .13), imibenconazole (B.1 .14), ipconazole (B.1 .15), metconazole (B.1 .17), myclobutanil (B.1 .18),
  • Delta14-reductase inhibitors aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8);
  • Inhibitors of 3-keto reductase fenhexamid (B.3.1 );
  • phenylamides or acyl amino acid fungicides benalaxyl (C.1.1 ), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1 .4), metalaxyl-M (mefenoxam, C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);
  • hymexazole C.2.1
  • octhilinone C.2.2
  • oxolinic acid C.2.3
  • bupirimate C.2.4
  • 5-fluorocytosine C.2.5
  • 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine C.2.6
  • 5-fluoro-2-(4- fluorophenylmethoxy)pyrimidin-4-amine C.2.7
  • tubulin inhibitors such as benzimidazoles, thiophanates: benomyl (D1.1 ), carbendazim (D1.2), fuberidazole (D1.3), thiabendazole (D1.4), thiophanate-methyl (D1 .5); triazolopyrimidi- nes: 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine (D1.6);
  • diethofencarb (D2.1 ), ethaboxam (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5), metrafenone (D2.6), pyriofenone (D2.7);
  • - methionine synthesis inhibitors anilino-pyrimidines: cyprodinil (E.1.1 ), mepanipyrim (E.1.2), pyrimethanil (E.1.3);
  • blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6), polyoxine (E.2.7), validamycin A (E.2.8);
  • MAP / histidine kinase inhibitors fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fenpiclonil (F.1.5), fludioxonil (F.1.6);
  • G protein inhibitors quinoxyfen (F.2.1 );
  • edifenphos (G.1 .1 ), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1 .4);
  • lipid peroxidation dicloran (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
  • phospholipid biosynthesis and cell wall deposition dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7) and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4- fluorophenyl) ester (G.3.8);
  • thio- and dithiocarbamates ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
  • organochlorine compounds e. g. phthalimides, sulfamides, chloronitriles: anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1), N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide (H.3.12);
  • organochlorine compounds e. g. phthalimides, sulfamides, chloronitriles
  • guanidines and others guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3), guaza- tine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H-[1 ,4]dithiino[2,3- c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10);
  • inhibitors of glucan synthesis validamycin (1.1.1), polyoxin B (1.1 .2);
  • - melanin synthesis inhibitors pyroquilon (1.2.1 ), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (1.2.5);
  • acibenzolar-S-methyl J.1.1
  • probenazole J.1 .2
  • isotianil J.1.3
  • tiadinil J.1 .4
  • prohexa- dione-calcium J.1.5
  • phosphonates fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), potassium or sodium bicarbonate (J.1 .9);
  • bronopol K.1 .1
  • chinomethionat K.1.2
  • cyflufenamid K.1.3
  • cymoxanil K.1.4
  • dazomet K.1.5
  • debacarb K.1.6
  • diclomezine K.1.7
  • difenzoquat K.1.8
  • difenzoquat-methylsulfate K.1.9
  • diphenylamin K.1.10
  • fenpyrazamine K.1.11
  • flumetover K.1.12
  • flusulfamide K.1.13
  • flutianil K.1.14)
  • methasulfocarb K.1.15), nitrapyrin (K.1.16), nitrothal-isopropyl (K.1.18), oxathiapiprolin (K.1.19), tolprocarb (K.1.20), oxin-copper (K.1.21), proquinazid
  • fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net pesticides/); these substances are commercially available.
  • fungicides described by lUPAC nomenclature, their preparation and their pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197;
  • Suitable mixing partners for the compounds of the invention also include biopesticides.
  • Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides fall into two major classes, microbial and biochemical pesticides:
  • Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.
  • Biochemical pesticides are naturally occurring substances or or structurally-similar and functionally identical to a naturally-occurring substance and extracts from biological sources that control pests or provide other crop protection uses as defined below, but have non-toxic mode of actions (such as growth or developmental regulation, attractents, repellents or defence activators (e.g. induced resistance) and are relatively non-toxic to mammals.
  • Biopesticides for use against crop diseases have already established themselves on a variety of crops. For example, biopesticides already play an important role in controlling downy mildew diseases. Their benefits include: a 0-Day Pre-Harvest Interval, the ability to use under moderate to severe disease pressure, and the ability to use in mixture or in a rotational program with other registered pesticides.
  • Biopesticidal seed treatments are e.g. used to control soil borne fungal pathogens that cause seed rots, damping-off, root rot and seedling blights. They can also be used to control internal seed borne fungal pathogens as well as fungal pathogens that are on the surface of the seed.
  • Many biopesticidal products also show capacities to stimulate plant host defenses and other physiological processes that can make treated crops more resistant to a variety of biotic and abiotic stresses or can regulate plant growth. Many biopesticidal products also show capacities to stimulate plant health, plant growth and/or yield enhancing activity.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the invention or a mixture thereof.
  • An agrochemical composition comprises a pesticidally effective amount of a compound of the invention or a mixture thereof.
  • the term "pesticidally effective amount” is defined below.
  • compositions e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi- ers and binders.
  • suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi- ers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo-'hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalene, alky
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch;
  • fertilizers e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas
  • products of vegetable origin e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth- oxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are homo- or copolymers of
  • Suitable cationic surfactants are quaternary surfactants, e.g. quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers.
  • polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the invention on the target.
  • surfactants mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • alcohol alkoxylates are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%.
  • a water-soluble solvent e.g. alcohols
  • the active substance dissolves upon dilution with water.
  • a compound I according to the invention 5-25 wt% of a compound I according to the invention and 1-10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
  • dispersant e. g. polyvinylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a compound I according to the invention 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active sub-stance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0,1-2 wt% thickener e.g. xanthan gum
  • up to 100 wt% water 100 wt% water
  • Dilution with water gives a stable suspension of the active sub-stance.
  • binder e.g. polyvinylalcohol
  • 50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -3 wt% wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a compound I according to the invention In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. car- boxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1-5 wt% thickener e.g. car- boxymethylcellulose
  • 5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alkohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g.
  • methylmethacrylate, methacrylic acid and a di- or triacrylate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • a protective colloid e.g. polyvinyl alcohol
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylme- thene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a polyamine e.g. hexamethylenediamine
  • the monomers amount to 1-10 wt%.
  • Dustable powders (DP, DS)
  • 1-10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • 0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • solid carrier e.g. silicate
  • 1-50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • organic solvent e.g. aromatic hydrocarbon.
  • compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions cormprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the in- vention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components e. g. components comprising compounds of the invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
  • the compounds of the invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the invention.
  • the compounds of the invention are also suitable for use in combating or controlling animal pests. Therefore, the invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the invention.
  • the compounds of the invention are effective through both contact and ingestion.
  • the compounds of the invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
  • the compounds of the invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above.
  • the components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture "in situ" on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
  • Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application.
  • Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection.
  • Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting.
  • furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow.
  • Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment.
  • pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.
  • contacting includes both direct contact (applying the
  • animal pest includes arthropods, gastropods, and nematodes.
  • Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.
  • Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
  • crop refers to both, growing and harvested crops.
  • plant includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
  • iceberg lettuce chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g.
  • Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof.
  • Plants which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice.
  • rapeseed e.g. oilseed rape
  • the one or more mutagenized or integrated genes are preferably selected from pat, epsps, cryl Ab, bar, cryl Fa2, cryl Ac, cry34Ab1 , cry35AB1 , cry3A, cryF, cryl F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asnl , and ppo5.
  • the mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant.
  • Such properties include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control.
  • herbicide tolerance e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance
  • mutagenesis e.g. Clearfield® oilseed rape being tolerant to imidazolinones, e.g. imazamox.
  • genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names
  • Insect resistance is of importance, in particular lepidopteran insect resistance and coleopteran insect resistance. Insect resistance is typically achieved by modifying plants by integrating cry and/or vip genes, which were isolated from Bacillus thuringiensis (Bt), and code for the respective Bt toxins.
  • Bt Bacillus thuringiensis
  • Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance.
  • the pesticidal activity of the compounds of the invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.
  • plant propagation material refers to 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.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
  • 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 combinations
  • 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 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 .
  • the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
  • the compounds of the invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects.
  • the invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermination with a compound of the invention.
  • the protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods.
  • seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • the invention also comprises seeds coated with or containing the active compound.
  • coated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
  • Suitable seed is e.g. seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, e.g. seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
  • the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
  • Conventional seed treatment formulations include e.g. flowable concentrates FS, solutions LS, suspoemulsions (SE), 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. Preferably, the formulations are applied such that germination is not included.
  • the active substance concentrations in ready-to-use formulations are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight.
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 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.
  • Especially preferred FS formulations of the compounds of the invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g.
  • a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
  • a binder sticker /adhesion agent
  • a preservative such as a biocide, antioxidant or the like
  • the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
  • the invention therefore also relates to seed comprising a compound of the invention, or an agriculturally useful salt thereof, as defined herein.
  • the amount of the compound of the invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
  • the compounds of the present invention may also be used for improving the health of a plant. Therefore, the present invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the invention.
  • an effective and non-phytotoxic amount means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.
  • plant and “plant propagation material” are defined above.
  • Plant health is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (e.g. increased biomass and/or increased content of valuable ingredients), quality (e.g. improved content or composition of certain ingredients or shelf life), plant vigour (e.g. improved plant growth and/or greener leaves ("greening effect"), tolerance to abiotic e.g. drought) and/or biotic stress (e.g. disease) and production efficiency (e.g. harvesting efficiency, processability).
  • yield e.g. increased biomass and/or increased content of valuable ingredients
  • quality e.g. improved content or composition of certain ingredients or shelf life
  • plant vigour e.g. improved plant growth and/or greener leaves ("greening effect")
  • tolerance to abiotic e.g. drought e.g. drought
  • biotic stress e.g. disease
  • production efficiency e.g. harvesting efficiency, processability
  • the above identified indicators for the health condition of a plant may be interdependent and may result from each other.
  • Each indicator is defined in the art and can be determined by methods known to a skilled person.
  • the compounds of the invention are also suitable for use against non-crop insect pests.
  • compounds of the invention can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied).
  • drenching and rodding methods can be used.
  • non-crop insect pest refers to pests, which are particularly relevant for non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitos, crickets, or cockroaches.
  • the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).
  • the bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it.
  • the attractiveness can be manipulated by using feeding stimulants or sex pheromones.
  • Food stimulants are chosen, e.g. 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.
  • 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 (e.g. http://www.pherobase.com), and are known to those skilled in the art.
  • the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.
  • Formulations of the compounds of the invention as aerosols are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches.
  • Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries such as emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants.
  • the oil spray formulations differ from the aerosol recipes in that no propellants are used.
  • the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
  • the compounds of the invention and its 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 e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis
  • compounds of the invention and its 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, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.
  • the compounds of the invention and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, 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).
  • Customary application rates in the protection of materials are, e.g. from 0.001 g to 2000 g or from 0.01 g to 1000 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 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.
  • the compounds of the the invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:
  • insects from the order of Lepidoptera e.g. Achroia grisella, Acleris spp. such as A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A.
  • ( Thermesia) spp. such as A. gemma talis; Apamea spp., Aproaerema modicella, Archips spp. such as A. argyrospila, A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella, Argyroploce spp., Argyrotaenia spp. such as A.
  • Athetis mindara Austroasca viridi- grisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C. podana; Cactoblastis cactorum, Cadra cautella, Calingo brazilien- s/5, Caloptilis theivora, Capua reticulana, Carposina spp. such as C.
  • Heliothis zea Heliothis zea
  • Heliothis spp. such as H. assulta, H. subflexa, H. virescens
  • Hellula spp. such as H. undalis, H. rogatalis
  • Helocoverpa gelotopoeon Hemileuca oliviae
  • Herpetogramma Iicarsisalis Hibernia defoliaria, Hofmannophila pseudospretella
  • Homoeosoma electellum Homona magnanima, Hypena scabra, Hyphantria cunea
  • Hyponomeuta padella Hyponomeuta malinellus, Kakivoria flavofasciata
  • Keiferia lycopersicella Lambdina fiscellaria fiscellaria, Lambdina fiscellaria lugubrosa, Lamprosema indicata, Laspeyresia molesta, Leguminivora
  • Mamestra spp. such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulalis, Megaiopyge lanata, Meianchra picta, Meianitis leda, Mods spp. such as M. lapites, M.
  • Phthorimaea spp. such as P. operculella; Phyllocnistis citrella, Phyllonorycter spp. such as P. blancardella, P. crataegella, P. issikii, P. ringoniella; Pieris spp. such as P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. such as P. flavedana, P. idaeusalis, P.
  • stultana Platyptilia carduidactyla, Plebejus argus, Plodia interpunctella, Plus/a spp, Plutella maculipennis, Plutella xylostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus lepigone, Pseudaletia spp. such as P. sequax, P.
  • S. exitiosa such as S. exitiosa, Tecia solanivora, Telehin licus, Thaumatopoea pityocampa, Thaumatotibia (-Cryptophlebia) le
  • Thaumetopoea pityocampa Thecla spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella, Tinea spp. such as T. cloacella, T. pellionella; Tineola bisselliella, Tortrixspp. such as T. viridana; Trichophaga tapetzella, Trichoplusia spp. such as T. ni; Tuta
  • Udea spp. such as U. rubigalis, U. rubigalis; Virachola spp.
  • insects from the order of Coleoptera e.g. Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. such as A. anxius, A. planipennis, A. sinuatus;
  • Agriotes spp. such as A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus,
  • Attagenus spp. Aulacophora femora/is, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B. rufimanus; Byctiscus betulae, Callidiellum rufipenne, Callopistria floridensis, Callosobruchus chinensis, Cameraria ohridella, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as C. assimilis, C. napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. such as C. vespertinus;
  • Curculio spp. Cylindrocopturus spp., Cyclocephala spp., Dactylispa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undecimpunctata, D. speciosa, D. longicornis, D. semipunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera, Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis), Enaphalodes rufulus, Epilachna spp. such as E. varivestis, E.
  • vigintioctomaculata Epitrix pp. such as E. hirtipennis, E. similaris; Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp. such as H. brunneipennis, H.
  • hypomeces squamosus Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp. such as L. bilineata, L. melanopus; Leptinotarsa spp. such as L decemlineata; Leptispa pygmaea, Limonius californicus, Lisso- rhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp. such as L.
  • alternatus such as alternatus; Naupactus xanthographus, Niptus hololeucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros, Oryzaephilus surina men- sis, Oryzaphagus oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Otiorrhynchus sulca- tus, Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon spp. such as P. brassi- cae, P.
  • Saperda Candida Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomor- phus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretani- cus, Tribolium spp. such as T.
  • insects from the order of Diptera e.g. Aedes spp. such as A. aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A. gam- biae, A. leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A. sinensis; Bac- trocera invadens, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capi- tata, Chrysomyia spp. such as C.
  • Aedes spp. such as A. aegypti, A. albopictus, A. vexans
  • Anastrepha ludens Anopheles spp.
  • A. albimanus
  • Geomyza tipunctata, Glossina spp. such as G. fuscipes, G. mor- sitans, G. pa/pa/is, G. tachinoides; Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppobosca spp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. trifolii; Lucilia spp. such as L. caprina, L. cuprina, L.
  • insects from the order of Thysanoptera e.g. Basothrips biformis, Dichromothrips corbetti, Di- chromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F. occidentalis, F. tritici; Helioth rips spp., Hercinothrips femoralis, Kakothrips spp., Micro- cephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphoro- thrips cruentatus, Scirtothrips spp.
  • insects from the order of Hemiptera e.g. Acizzia jamatonica, Acrosternum spp. such as A. hilare; Acyrthosipon spp. such as A. onobrychis, A. pisum; Adelges laricis, Adelges tsugae, Ad el phocoris spp., such as A. rapidus, A.
  • C. hemipterus such as C. hemipterus, C. lectularius; Coccomytilus halli, Coccus spp. such as C. hesperidum, C. pseudomagnoliarurrr, Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis,
  • Idiocerus spp. Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus floccissimus, Lepidosaphes spp. such as L ulmi; Leptocorisa pp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L. hesperus, L. lineolaris, L. pra- tensis; Maconellicoccus hirsutus, Marchalina helienica, Macropes excavatus, Macrosiphum spp. such as M. rosae, M.
  • Nasonovia ribis-nigri Nasonovia ribis-nigri, Neotoxoptera formosana, Neomegalotomus spp, Nephotettix spp. such as N. malayanus, N. nigropictus, N. parvus, N. vi- rescens; Nezara spp. such as N. viridula; Niiaparvata lugens, Nysius huttoni, Oebalus spp. such as O.
  • P. devastatrix Piesma quadrata, Piezodorus spp. such as P. guildinii; Pin- naspis aspidistrae, Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta, Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such as P. comstocki; Psylla spp. such as P.
  • Pteromalus spp. Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalo- siphum spp. such as /?. pseudobrassicas, R. insertum, R. maidis, R.
  • T. perditor such as accerra, T. perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. such as aurantii; Trialeurodes spp. such as 7 ⁇ abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as £/ c/iVjr) 6/. yanonensis; and Viteus vitifolii,
  • Insects from the order Hymenoptera e.g. Acanthomyops interjectus, Athalia rosae, Atta spp. such as A. capiguara, A. cephaiotes, A. cephaiotes, A. laevigata, A. robusta, A. sexdens, A. tex- ana, Bombus spp., Brachymyrmex spp., Camponotus spp. such as C. floridanus, C. pennsyl- vanicus, C.
  • Hymenoptera e.g. Acanthomyops interjectus, Athalia rosae, Atta spp.
  • A. capiguara such as A. cephaiotes, A. cephaiotes, A. laevigata, A. robusta, A. sexdens, A. tex- ana, Bombus spp., Brachymyrmex spp., Camponotus
  • M pharaonis such as M pharaonis, Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechina lon- gicornis, Paravespula spp., such as P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. such as P. megacephala; Pogonomyrmex pp. such as P. barbatus, P. californicus, Polistes ru- biginosa, Prenolepis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenop- sis spp. such as S.
  • geminata S.invicta, S. molesta, S. richteri, S. xyloni, Sphecius speciosus, Sphexspp., Tapinoma spp. such as T. melanocephalum, T. sessile; Tetramorium spp. such as T. caespitum, T. bicarinatum, Vespa spp. such as V. crabro; Vespula spp. such as V. squamo- sal; Wasmannia auropunctata, Xylocopa sp;
  • Insects from the order Orthoptera e.g. Acheta domesticus, Calliptamus italicus, Chortoicetes terminifera, Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllo- talpa spp. such as G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis,
  • Kraussaria angulifera Locusta spp. such as L. migratoria, L. pardalina; Melanoplus spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus; Nomadacris sep- temfasciata, Oedaleus senegalensis, Scapteriscus spp., Schistocerca spp. such as S. ameri- cana, S. gregaria, Stemopelmatus spp., Tachycines asynamorus, and Zonozerus variegatus; Pests from the Class Arachnida e.g.
  • Amblyomma spp. e.g. A. americanum, A. variegatum, A. maculatum
  • Argas spp. such as A. persicu
  • Boophilus spp. such as B. annulatus, B. decoloratus, B. microplus, Dermacentor spp. such as D.silvarum, D. andersoni, D. variabilis
  • Hyalomma spp. such as H. truncatum
  • Ixodes spp. such as /. ricinus, I. rubicundus, I.
  • scapularis I. holocyclus, I. pacificus, Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Orni- thonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. such as P. ovis,
  • Rhipicephalus spp. such as R. sanguineus, R. appendiculatus, Rhipicephalus everts/, Rhizogly- phus spp., Sarcoptes spp. such asS. Scabier, and Family Eriophyidae including Aceria spp. such as A. sheldoni, A. anthocoptes, Acallitus spp., Aculops spp. such as A. lycopersici, A. pel- ekassi, Aculus spp. such as A.
  • Tetranychus spp. Family Tetranychidae including Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp. such as 7 ⁇ cinnabarinus, T. evansi, T. kan- zawai, T, pacificus, T. phaseulus, T. telarius and urticae; Bryobia praetiosa; Panonychus spp. such as P. £///77/; P. ofrv; Metatetranychus spp. and Oligonychus s p. such as C. pratensis, O.
  • Family Pyemotidae including Pyemotes tritici, Tyrophagus putrescen- tiae; Family Acaridae including Acarus siro, Family Araneida including Latrodectus mactans, Tegenaria ag rest is, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosceles reclusa;
  • Pests from the Phylum Nematoda e.g. plant parasitic nematodes such as root-knot nema- todes, Meloidogyne spp. such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H. schachtii, H. trifolii; Seed gall nematodes, Anguina spp.; Stem and foliar nematodes, Aphelen- choides spp. such as A.
  • plant parasitic nematodes such as root-knot nema- todes, Meloidogyne spp. such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp.
  • Awl nematodes Dolichodorus spp.
  • Spiral nematodes Heliocotylenchus multicinctus
  • Sheath and sheathoid nematodes Hemicyciiophora spp. and Hemicriconemoides spp.
  • Hirshmanniella spp. ⁇ Lance nematodes, Hoploaimus spp.
  • False rootknot nematodes Nacobbus spp.
  • Needle nematodes Longidorus spp. such as Z.. elongatus
  • Lesion nematodes Pratylenchus spp. such as .
  • brachyurus P. neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopholus spp. such as ?. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform nematodes, Rotylenchus spp. such as /?. /r>- bustus, R. reniformis; Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as 7 ⁇ obtusus, T. primitivus; Paratrichodorus spp. such as P.
  • Stunt nematodes Tylenchorhyn- chus spp. such as T. claytoni, T. dub/us
  • Citrus nematodes Tylenchulus spp. such as 7 ⁇ se/ro- penetrans
  • Dagger nematodes Xiphinema spp.
  • other plant parasitic nematode species such as T. claytoni, T. dub/us
  • Insects from the order Isoptera e.g. Calotermes flavicollis, Coptotermes spp. such as C. for- mosanus, C. gestroi, C. acinaciformis; Cornitermes cumulans, Cryptotermes spp. such as C. brevis, C. cavifrons; Globitermes sulfureus, Heterotermes spp. such as H. aureus, H. longiceps, H. tenuis; Leucotermes flavipes, Odontotermes spp., Incisitermes spp. such as /. minor, I.
  • Neotermes spp. such as M. darwiniensis Neocapritermes spp. such as N. opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp. such as Z. angusticollis, Z. nevadensis, Reticulitermes spp. such as ?. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. santonensis, R. virgin icus; Termes natalensis,
  • Thysanura e.g. Lepisma saccharina , Ctenolepisma urbana, and Ther- mobia domestica
  • Pests from the class Chilopoda e.g. Geophilus spp., Scutigera spp. such as Scutigera coleop- trata,
  • Pests from the class Diplopoda e.g. Blaniulus guttulatus, Ju/us spp., Narceus spp.,
  • Pests from the class Symphyla e.g. Scutigerella immaculata
  • Insects from the order Collembola e.g. Onychiurus spp., such as Onychiurus armatus, Pests from the order Isopoda e.g., Armadillidium vulgare, Oniscus asellus, Porcellio scaber, Insects from the order Phthiraptera, e.g. Damalinia spp., Pediculus spp. such as Pediculus hu- manus capitis, Pediculus humanus corporis, Pediculus humanus humanus humanus; Pthirus pubis, Haematopinus spp.
  • Onychiurus spp. such as Onychiurus armatus
  • Pests from the order Isopoda e.g., Armadillidium vulgare, Oniscus asellus, Porcellio scaber
  • Insects from the order Phthiraptera e.g. Damalinia spp.
  • Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, e.g. Dreissena spp.; class Gastropoda, e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Ga/ba spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp. /from the class of the helminths, e.g.
  • the compounds of the invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the invention also relates to the use of a compound of the invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites. Furthermore, the invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiti- cidally effective amount of a compound of the invention.
  • the invention also relates to the non-therapeutic use of compounds of the invention for treating or protecting animals against infestation and infection by parasites. Moreover, the invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.
  • the compounds of the invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the invention relates to a method of combating or controlling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the invention.
  • the invention also relates to the non-therapeutic use of compounds of the invention for controlling or combating parasites. Moreover, the invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.
  • the compounds of the invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds of the invention can be applied to any and all developmental stages.
  • the compounds of the invention can be applied as such or in form of compositions comprising the compounds of the invention.
  • the compounds of the invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.
  • a mixing partner which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Narasin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.
  • the compounds of the invention and compositions comprising them can be applied orally, par- enterally or topically, e.g. dermally.
  • the compounds of the invention can be systemically or non- systemically effective.
  • the application can be carried out prophylactically, therapeutically or non-therapeutically. Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected.
  • the term "contacting" includes both direct contact (applying the compounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at it's locus for the latter) and indirect con- tact (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 the compounds of the invention.
  • locus means the habitat, food supply, breeding ground, area, material or environ- ment in which a parasite is growing or may grow outside of the animal.
  • parasites includes endo- and ectoparasites. In some embodiments of the invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. 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, chiggers, gnats, mosquitoes and fleas.
  • the compounds of the invention are especially useful for combating parasites of the following orders and species, respectively:
  • fleas e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Peri- planeta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis;1 ⁇ es, mosquitoes (Diptera), e.g.
  • Pediculus humanus capitis Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bo vf cola bo vis, Menopon gallinae, Menacanthus stramineus and Solenopotes ca pi I la tus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g.
  • Haematopinus spp. Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.
  • Mallophagida suborders Arnblycerina and Ischnocerina), e.g. 7/7- menopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.
  • Roundworms Nematoda Wipeworms and Trichinosis (Trichosyringida), e.g.
  • Trichinellidae Trichinella spp.
  • Trichuridae ' Trichuris spp. Capillaria spp.
  • Rhabditida e.g. Rhabditis spp.
  • Strongyloides spp. Helicephalobus s/j ./ Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp.
  • Ascaris lumbricoides Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris e ⁇ ' Camallanida, e.g. Dracunculus medinensis (guinea worm); Spirurida, e.g.
  • Faciola spp. Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp:, Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.
  • animal includes warm-blooded animals (including humans) and fish.
  • 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.
  • domestic animals such as dogs or cats.
  • 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/com- positions used in the invention.
  • a parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
  • the compounds of the 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 formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules.
  • the formula I compounds 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 the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
  • the formula I compounds may be administered to animals parenterally, e.g. by intraruminal, intramuscular, intravenous or subcutaneous injection.
  • the formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection.
  • the formula I compounds may be formulated into an implant for subcutaneous administration.
  • the formula I compound 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 formula I compound.
  • the formula I compounds 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 preferably 1 ppm to 3,000 ppm of the formula I compound.
  • the formula I compounds may be formulated as ear tags for animals, particu- larly 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;
  • 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 suita- ble solvent and optionally adding further auxiliaries such as acids, bases, buffer salts, preservatives, and solubilizers.
  • auxiliaries for injection solutions are known in the art. The solutions are filtered and filled sterile.
  • 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 according to what is described above for injection solutions, sterile procedures not being necessary.
  • 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 ointment-like consistency results. Suitable thickeners are known in the art.
  • Pour-on formulations are poured or sprayed onto limited areas of the skin, the active com- pound 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.
  • suitable skin-compatible solvents or solvent mixtures If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art.
  • 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), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.
  • 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 substances, preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.
  • 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 excipi- ents, if appropriate with addition of auxiliaries, and brought into the desired form.
  • auxiliaries for this purpose are known in the art.
  • compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the invention.
  • Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.
  • Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.
  • the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.
  • Topical application may be conducted with compound-containing shaped articles such as col- lars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
  • compound-containing shaped articles such as col- lars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
  • solid formulations which release compounds of the 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.
  • Compounds can be characterized e.g. by coupled High Performance Liquid Chromatography / mass spectrometry (HPLC/MS), by 1 H-NMR and/or by their melting points.
  • HPLC/MS High Performance Liquid Chromatography / mass spectrometry
  • Abbreviations used are: d for day(s), h for hour(s), min for minute(s), r.t./room temperature for 20-25°C, Rt for retention time; Ph for phenyl, OAc for acetate, CH for cyclohexane, EtOAc for ethyl acetate, and t-BuOH for tert-butanol.
  • Example V 1-[2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]spiro[4H- thieno[2,3-c]furan-6,3'-azetidine]-1 '-yl]-2-methylsulfonyl-ethanone [C-10]
  • Step 1 tert-butyl 3-hydroxy-3-[3-(hydroxymethyl)-2-thienyl]azetidine-1-carboxylate
  • Step 2 tert-butyl spiro[4H-thieno[2,3-c]furan-6,3'-azetidine]-1 '-carboxylate
  • Step 3 tert-butyl 2-bromospiro[4H-thieno[2,3-c]furan-6,3'-azetidine]-1 '-carboxylate
  • Step 4 tert-butyl 2-acetylspiro[4H-thieno[2,3-c]furan-6,3'-azetidine]-1'-carboxylate
  • Step 5 tert-butyl 2-[3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-3-hydroxy-butanoyl]spi- ro[4H-thieno[2,3-c]furan-6,3'-azetidine]-1'-carboxylate
  • Step 6 tert-butyl 2-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[4H- th ieno[2,3-c]fu ran-6 ,3'-azetidi ne]- 1 '-carboxylate
  • the resulting reaction mixture was stirred at 80°C for 2 h, before it was cooled to r.t.. MTBE and aqueous 5% K2CO3 solution was added it was stirred vigorously. The aqueous layer was removed and discarded. The organic layer was washed with aqueous 2 N HCI, saturated aqueous NaHCC>3 solution and brine, before it was dried over Na2SC>4. After concentration in vacuum, the crude title compound (8.20 g, quantita- tive) was obtained and used in the next transformation without further purification.
  • Step 7 tert-butyl 2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3- yl]spiro[4H-thieno[2,3-c]furan-6,3'-azetidine]-1 '-carboxylate
  • Step 8 2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]spiro[4H- thieno[2,3-c]furan-6,3'-azetidin-1 -ium];2,2,2-trifluoroacetate
  • Step 9 preparation of 1-[2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3- yl]spiro[4H-thieno[2,3-c]furan-6,3'-azetidine]-1'-yl]-2-methylsulfonyl-ethanone
  • Example 2 1-[2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]spiro[4,5- dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1 '-yl]propan-1-one [C-1]
  • Step 1 tert-butyl 3-hydroxy-3-[3-(2-hydroxyethyl)-2-thienyl]azetidine-1-carboxylate
  • Step 2 tert-butyl spiro[4,5-dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1'-carboxylate
  • a solution of tert-butyl 3-hydroxy-3-[3-(2-hydroxyethyl)-2-thienyl]azetidine-1-carboxylate (Example 2, Step 1 , 7.50 g, 25.1 mmol, 1.00 equiv.) in THF (150 mL) was added triethyl amine (17.4 mL, 125 mmol, 5 equiv.) and a solution of mesyl chloride (2.3 mL, 30 mmol, 1.2 equiv.) in THF (2 mL) at 0°C.
  • Step 3 tert-butyl 2-bromospiro[4,5-dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1 '-carboxylate
  • Step 2 a solution of tert-butyl spiro[4,5-dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1 '-carboxylate (Step 2, 5.66 g, 20.1 mmol, 1.00 equiv.) and DMAP (122 mg, 1.01 mmol, 0.05 equiv.) in ace- tonitrile (100 mL) was added a solution of NBS (4.30 g, 24.1 mmol, 1.20 equiv.) in acetonitrile (70 mL) at 0°C.
  • Step 4 tert-butyl 2-acetylspiro[4,5-dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1 '-carboxylate
  • Step 3 tert-butyl 2-bromospiro[4,5-dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1 '-carboxylate
  • N-butyl vinyl ether (6.20 mL, 47.9 mmol, 2.5 equiv.)
  • Pd(OAc)2 (258 mg, 1.15 mmol, 0.06 equiv.
  • 1 ,3-bis(diphenylphosphino)propane 947 mg, 2.30 mmol, 12.0 mol-%), triethylamine (5.4 mL, 38 mmol, 2.0 equiv.), and 1-butanol (100 mL)
  • Step 5 tert-butyl 2-[3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-3-hydroxy-buta- noyl]spiro[4,5-dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1 '-carboxylate
  • Step 6 tert-butyl 2-[(E/Z)-3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]spiro[4,5- dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1 '-carboxylate
  • tert-butyl 2-[3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-3-hydroxy-buta- noyl]spiro[4,5-dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1'-carboxylate (Step 5, 5.95 g, 10.2 mmol, LOOequiv.) in toluene (100 ml_) was added pyridine (4.1 ml_, 51 mmol, 5 equiv.) and thio- nyl chloride
  • the resulting reaction mixture was stirred at 80°C for 2 h, before it was cooled to r.t.. MTBE and aqueous 5% K2CO3 solution was added it was stirred vigorously. The aqueous layer was removed and discarded. The organic layer was washed with aqueous 2 N HCI, saturated aqueous NaHCC>3 solution and brine, before it was dried over Na2S0 4 . After concentration in vacuum, the crude title compound (5.3 g, 92%) was obtained and used in the next transformation without further purification.
  • Step 7 tert-butyl 2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3- yl]spiro[4,5-dihydrothieno[2,3-c]pyran-7,3'-azetidine]-1 '-carboxylate
  • Step 8 2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]spiro[4,5-dihy- drothieno[2,3-c]pyran-7,3'-azetidin-1-ium];2,2,2-trifluoroacetate
  • Step 9 1 -[2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]spiro[4,5-dihy- drothieno[2,3-c]pyran-7,3'-azetidine]-1 '-yl]propan-1-one
  • Step 1 tert-butyl N-[(2Z)-2-(dimethylaminomethylene)-3-oxo-cyclohexyl]carbamate
  • Step 2 [3-(tert-butoxycarbonylamino)-2-formyl-cyclohexen-1-yl] trifluoromethanesulfonate
  • tert-butyl N-[(2Z)-2-(dimethylaminomethylene)-3-oxo-cyclo- hexyl]carbamate 4.4 g
  • 2,6-di-tert-butylpyridine 9.4 g, 49 mmol
  • CH 2 CI 2 120 mL
  • triflic anhydride 9.2 g, 33 mmol
  • Step 3 tert-butyl N-(2-acetyl-4,5,6,7-tetrahydrobenzothiophen-4-yl)carbamate
  • Step 4 tert-butyl N-[2-[3-(3,5-dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-3-hydroxy-butanoyl]- 4,5,6,7-tetrahydrobenzothiophen-4-yl]carbamate
  • Step 5 tert-butyl N-[2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]- 4,5,6,7-tetrahydrobenzothiophen-4-yl]carbamate
  • Step 6 [2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-4,5,6,7-tetrahy- drobenzothiophen-4-yl]ammonium trifluoroacetate
  • Step 7 N-[2-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-4,5,6,7- tetrahydrobenzothiophen-4-yl]-2-methylsulfonyl-acetamide
  • Example B-1 Action on Yellow fever mosquito (Aedes aegypti)
  • test unit For evaluating control of yellow fever mosquito ⁇ Aedes aegypti the test unit consisted of 96- well-microtiter plates containing 200 ⁇ of tap water per well and 5-15 freshly hatched A. aegypti larvae.
  • the active compounds were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5 ⁇ , using a custom built micro atomizer, at two replications.
  • microtiter plates were incubated at 28 + 1 °C, 80 + 5 % RH for 2 days. Larval mortality was then visually assessed.
  • Example B-2 Action on Orchid thrips (dichromothrips corbetti)
  • Dichromothrips corbetti ' adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions.
  • the test compound is diluted in a 1 : 1 mixture of acetone:water (vohvol), plus Kinetic® HV at a rate of 0.01 % v/v.
  • Thrips potency of each compound was evaluated by using a floral-immersion technique. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry in Petri dishes. Treated petals were placed into individual re-sealable plastic along with about 20 adult thrips. All test arenas were held under continuous light and a temperature of about 28°C for duration of the assay. After 3 days, the numbers of live thrips were counted on each petal. The percent mortality was recorded 72 hours after treatment.
  • test unit For evaluating control of boll weevil [Anthonomus grandis) the test unit consisted of 96-well- microtiter plates containing an insect diet and 5-10 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 5 ⁇ , using a custom built micro atomizer, at two replications.
  • microtiter plates were incubated at about 25 + 1 °C and about 75 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
  • Example B-4 Action on Tobacco budworm (Heliothis virescens)
  • test unit For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96- well-microtiter plates containing an insect diet and 15-25 H. virescens 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 10 ⁇ , using a custom built micro atomizer, at two replications.
  • microtiter plates were incubated at about 28 + 1 °C and about 80 + 5
  • Example B-5 Action on Vetch aphid (Megoura viciae)
  • test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.
  • 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 leaf disks at 2.5 ⁇ , using a custom built micro atomizer, at two replications.
  • the leaf disks were air-dried and 5 - 8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed.
  • 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 DMSO
  • aphids were placed on the artificial membrane inside the microliter 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.
  • Example B-7 Action on Diamond back moth ⁇ Plutella xylostella
  • the active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone.
  • Surfactant Kinetic® HV
  • the test solution is prepared at the day of use.
  • Leaves of cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dishes lined with moist filter paper and inoculated with ten 3 rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damages were also recorded using a scale of 0- 100%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne de nouveaux composés de formule I, dans laquelle les variables sont telles que définies dans la description, des compositions les comprenant, des combinaisons de composés actifs comprenant ces composés et leur utilisation pour protéger des plantes contre une attaque ou une infestation par des organismes nuisibles invertébrés. La présente invention concerne en outre des semences comprenant ces composés.
PCT/EP2018/055539 2017-03-16 2018-03-07 Dihydroisoxazoles à substitution hétérobicyclique WO2018166855A1 (fr)

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