WO2015040405A2 - Produits chimiques agricoles - Google Patents

Produits chimiques agricoles Download PDF

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Publication number
WO2015040405A2
WO2015040405A2 PCT/GB2014/052841 GB2014052841W WO2015040405A2 WO 2015040405 A2 WO2015040405 A2 WO 2015040405A2 GB 2014052841 W GB2014052841 W GB 2014052841W WO 2015040405 A2 WO2015040405 A2 WO 2015040405A2
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spp
compound
alkyl
aryl
heteroaryl
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PCT/GB2014/052841
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English (en)
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WO2015040405A3 (fr
Inventor
Christopher URCH
William Thompson
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Redx Pharma Limited
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Publication of WO2015040405A3 publication Critical patent/WO2015040405A3/fr

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Classifications

    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/74—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 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings

Definitions

  • the present invention relates to compounds which are of use in the field of agriculture as nematicides, fungicides, insecticides and/or acaricides.
  • a new threat contributing to this is the emergence of chemical-resistant organisms, for example, glyphosate-resistant weeds in USA and strobilurin-resistant strains of septoria fungal species.
  • An aim of the present invention is to provide pesticides (e.g. fungicides) which have activity either non-selectively, i.e. broad spectrum activity, or which are active specifically against selective target organisms.
  • pesticides e.g. fungicides
  • activity either non-selectively, i.e. broad spectrum activity, or which are active specifically against selective target organisms.
  • An aim of the present invention is to provide compounds which are less persistent in the environment after use than prior art compounds.
  • the compounds of the present invention are less prone to bioaccumulation once in the food chain than prior art compounds.
  • Another aim of the invention is to provide compounds which are less harmful to humans than prior art compounds.
  • the compounds of the invention may be less harmful than prior art compounds to one or more of the following groups: amphibians, fish, mammals (including domesticated animals such as dogs, cats, cows, sheep, pigs, goats, etc), reptiles, birds, and beneficial invertebrates (e.g. bees and other insects, or worms), beneficial nematodes, beneficial fungi and nitrogen-fixing bacteria.
  • amphibians fish
  • mammals including domesticated animals such as dogs, cats, cows, sheep, pigs, goats, etc
  • reptiles birds
  • beneficial invertebrates e.g. bees and other insects, or worms
  • beneficial nematodes e.g. bees and other insects, or worms
  • beneficial nematodes e.g. bees and other insects, or worms
  • beneficial fungi fungi and nitrogen-fixing bacteria.
  • the compounds of the invention may be as active or more active than prior art compounds. They may have activity against organisms which have developed a resistance to prior art compounds. However, the present invention also concerns compounds which have a lower level of activity relative to that of prior art compoundscompound. These lower activity compounds are still effective as nematicides, fungicides, insecticides and/or acaricides but have other advantages relative to existing compounds such as, for example, a reduced environmental impact.
  • the compounds of the invention may be more selective than prior art compounds, i .e. they may have better, similar or even slightly lower activity than prior art compoundsagainst target species but have a significantly lower activity against non-target species (e.g. the crops which are being protected) .
  • This invention provides compounds that achieve one or more of the above aims.
  • the compounds may be active in their own right or may metabolise or react in aqueous media to yield an active compound.
  • X is independently selected from N and CR 5 ;
  • R 1 and R 2 are independently selected from the group comprising: H, Ci-Ce alkyl, -(CR 8 R 8 ) heteroaryl, -(CR 8 R 8 ) n -aryl , -(CR 8 R 8 ) n -aryl-Z-A, -(CR 8 R 8 ) n -heteroaryl-Z-A, -(CR 8 R 8 ) n -C 3 -C cycloalkyl, -(CR 8 R 8 ) n -heterocycloalkyl and Ci-C 8 -haloalkyl;
  • R 3 , R 4 and R 5 are independently selected from the group comprising: H, C1-C4 alkyl, -(CR 8 R 8 ) heteroaryl, -(CR 8 R 8 ) n -aryl, -(CR 8 R 8 ) n - C 3 -C 6 -cycloalkyl, -(CR 8 R 8 ) n -heterocycloalkyl, C1-C haloalkyl , bromo, nitro, OR 9 , SR 9 , cyano, C2-C4 alkenyl, C2-C4 alkynyl and NR 9 R 9 ;
  • R 6 is independently selected from the group comprising: H, -(CR 10 R 10 ) m R 11 and C(0)R 12 ;
  • R 7 is independently selected from: H , C1-C4 alkyl, C3-Cs-cycloalkyl and benzyl;
  • Z is independently selected from O, S and NR 9 ;
  • A is independently selected from aryl and heteroaryl
  • R 8 is independently at each occurrence selected from H, F, C1-C4 alkyl and C1-C4 haloalkyl
  • R 9 is independently at each occurrence selected from H, C1-C4 alkyl, C(0)-Ci-C4 alkyl, and Ci- C4 haloalkyi
  • R 10 is independently at each occurrence selected from H, F, C1-C4 alkyl and C1-C4 haloalkyi
  • R 1 is independently at each occurrence selected from the group comprising: H, Ci-Ce alkyl, - (CR 8 R 8 ) P -heteroaryl, -(CR 8 R 8 ) P -aryl, -(CR 8 R 8 ) P -aryl-Z-A, -(CR 8 R 8 ) P -heteroaryl-Z-A, -(CR 8 R 8 ) P - C 3 - Ce-cycloalkyl, -(CR 8 R 8 ) p -heterocycloalkyl and Ci-Cs-haloalkyl;
  • R 12 is independently selected from H, C1-C4 alkyl, C1-C4 haloalkyi, C3-C5 cycloalkyi;
  • n is an integer independently at each occurrence selected from 0, 1 , 2 and 3;
  • n is an integer independently at each occurrence selected from 0 and 1 ;
  • p is an integer independently at each occurrence selected from 0 and 1 ;
  • NR a R a , OR a , SR a , R a when present on neighbouring atoms in the aryl or heteroaryl group may, where chemically possible, together with the atoms to which they are attached form a ring which is fused to the aryl or heteroaryl group;
  • the compound may be a compound of formula la:
  • X is independently selected from N and CR 5 ;
  • R 1 and R 2 are independently selected from the group comprising: H, Ci-Ce alkyl, -(CR 8 R 8 ) n - heteroaryl, -(CR 8 R 8 ) n -aryl, -(CR 8 R 8 ) n -aryl-Z-A, -(CR 8 R 8 ) n -heteroaryl-Z-A, -(CR 8 R 8 ) n -C 3 -C 6 - cycloalkyl, -(CR 8 R 8 ) n -heterocycloalkyl and Ci-Ce-haloalkyl;
  • R 3 , R 4 and R 5 are independently selected from the group comprising: H, C1-C4 alkyl, -(CR 8 R 8 ) n - heteroaryl, -(CR 8 R 8 ) n -aryl, -(CR 8 R 8 ) n - C 3 -C 6 -cycloalkyl, -(CR 8 R 8 ) n -heterocycloalkyl, C1-C4- haloalkyl, halogen, nitro, OR 9 , SR 9 , cyano, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl and NR 9 R 9 ;
  • R 6 and R 7 are independently selected from the group comprising: H and -(CR 10 R 10 ) m R 1 1 ; Z is independently selected from O, S and NR 9 ;
  • A is independently selected from aryl and heteroaryl
  • R 8 is independently at each occurrence selected from H, C1-C4 alkyl and C1-C4 haloalkyi;
  • R 9 is independently at each occurrence selected from H, C1-C4 alkyl, C(0)-O-C4 alkyl, and O-
  • R 10 is independently at each occurrence selected from H, C1-C4 alkyl and C1-C4 haloalkyi; or wherein two R 0 groups which are attached to the same carbon form an oxo group;
  • R 1 is independently at each occurrence selected from the group comprising: H, O-Ce alkyl, -
  • n is an integer independently at each occurrence selected from 0, 1 , 2 and 3;
  • n is an integer independently at each occurrence selected from 0 and 1 ;
  • p is an integer independently at each occurrence selected from 0 and 1 ;
  • R a halo; nitro; cyano; NR a R a ; S0 3 R a ; S0 2 R a ; S0 2 NR a R a ; C02R a ; C(0)R a ; CONR a R a ; CH 2 NR a R a ;
  • ChbOR 8 and OR a wherein R a is selected from H, C1-C4 alkyl and C1-C4 haloalkyi; and wherein, in the case of an aryl group or heteroaryl group, any two of these substituents (e.g. N R a R a ,
  • OR a , SR a , R a when present on neighbouring atoms in the aryl or heteroaryl group may, where chemically possible, together with the atoms to which they are attached form a ring which is fused to the aryl or heteroaryl group;
  • the compound of formula I or la is a compound of formula II:
  • R ⁇ R 2 , R 3 , R 4 , R 6 and R 7 are as described above for compounds of formula I or formula 1a.
  • the compound of formula I is a compound of formula III:
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 5 and R 7 are as described above for compounds of formula I or formula la.
  • the compound of formula I or formula la is a compound of formula IV:
  • R ⁇ R 2 , R 6 and R 7 are as described above for compounds of formula I or formula la and wherein R 3 is independently selected from the group comprising: C1-C4 alkyl, Ci-C4-haloalkyl, bromo, cyano, C2-C4 alkenyl and C2-C4 alkynyl.
  • R 3 is independently selected from the group comprising: C1-C4 alkyl, -(CR 8 R 8 ) n -heteroaryl, -(CR 8 R 8 ) n -aryl, -(CR 8 R 8 ) r - cycloalkyl, -(CR 8 R 8 ) n -heterocycloalkyl, Ci-C4-haloalkyl, halogen, nitro, OR 9 , SR 9 , cyano, C2-C4 alkenyl, C2-C4 alkynyl and NR 9 R 9 .
  • the compound of formula I or formula la is a compound of formula V:
  • R ⁇ R 2 , R 6 and R 7 are as described above for compounds of formula I or formula la and wherein R 3 is as described above for compounds of formula IV.
  • the compound of formula I or formula la is a compound of formula VI :
  • R 1 , R 2 , R 6 and R 7 are as described above for compounds of formula I or formula la and wherein R 3 is as described above for compounds of formula IV.
  • the following embodiments apply to compounds of any of formulae (l)-(VI) (including la). These embodiments are independent and interchangeable. Any one embodiment may be combined with any other embodiment, where chemically allowed. In other words, any of the features described in the following embodiments may (where chemically allowable) be combined with the features described in one or more other embodiments. In particular, where a compound is exemplified or illustrated in this specification, any two or more of the embodiments listed below, expressed at any level of generality, which encompass that compound may be combined to provide a further embodiment which forms part of the present disclosure.
  • X is N Alternatively, X is CR 5
  • R and R 2 are not both H.
  • R is independently selected from the group comprising: Ci-Cs alkyl, -(CR 8 R 8 ) n -heteroaryl, - (CR 8 R 8 )n-aryl, -(CR 8 R 8 ) n -aryl-Z-A, -(CR 8 R 8 ) n -heteroaryl-Z-A, -(CR 8 R 8 ) n - C 3 -C 6 -cycloalkyl, - (CR 8 R 8 )n-heterocycloalkyl and Ci-Cs-haloalkyl.
  • R 1 is independently selected from the group comprising: d-Cs alkyl, -(CR 8 R 8 ) n -aryl, -(CR 8 R 8 ) n -aryl-Z-A and - (CR 8 R 8 ) n - Cs-Ce-cycloalkyl.
  • R 1 contains -(CR 8 R 8 ) n -
  • n is 0.
  • R 1 contains -(CR 8 R 8 ) n -
  • n is 1 or n is 2.
  • the -(CR 8 R 8 )- group adjacent to the N to which R is attached may be -CH(Me)-.
  • R 1 may be -(CR 8 R 8 ) n -aryl, e.g. -(CR 8 R 8 ) n -phenyl.
  • R 1 may be -CH(Me)Ph.
  • R 1 may also be -(CR 8 R 8 V Cs-Cs-cycloalkyl, e.g. -(CR 8 RV Cs-Cs-cycloalkyl.
  • R may be selected from -(CR 8 R 8 ) n -cyclobutyl, -(CR 8 R 8 ) complicat-c or -(CR 3 R 8 ) n -cyclopentyl.
  • R 1 may be (an illustrative example of a group in which n is 1) or (an illustrative example of a group in which n is 2).
  • R 1 may be cycloalkyl (i.e. n is 0), e.g. R 1 may be cyclopentyl.
  • R 1 may be Ci-Cs-alkyl.
  • R 1 may be propyl, butyl, pentyl, hexyl, heptyl or octyl.
  • These R 1 groups may be branched, and in some embodiments have a methyl group branching out from the carbon adjacent to the N to which R 1 is attached.
  • R may be heptyl and more specifically R 1 may be n-heptyl or R may be
  • R is -(CR 8 R 8 ) n -aryl-Z-A or -(CR 8 R 8 ) n -heteroaryl-Z-A.
  • n is preferably 0.
  • R 1 may be phenyl-Z-A or pyridyl-Z-A.
  • the Z-A is preferably at the para position of the phenyl or pyridyl ring relative to the N to which (CR 8 R 8 ) n is attached.
  • Z is preferably O.
  • A may be phenyl, which may be substituted, e.g. at the para-position.
  • A may be 4-trifluoromethylphenyl.
  • R 1 may be
  • R 2 may be selected from: H and C1-C4 alkyl. In a preferred embodiment, R 2 is H.
  • R 3 , R 4 and R 5 are independently selected from the group comprising: H , C1-C4 alkyl, Ci-C4-haloalkyl, bromo, cyano, C2-C4 alkenyl and C2-C4 alkynyl.
  • R 3 may be independently selected from the group comprising: H, C1-C4 alkyl, Ci-C4-haloalkyl, bromo, cyano, C2-C4 alkenyl and C2-C4 alkynyl.
  • R 3 is not H .
  • R 3 is independently selected from the group comprising: d-C 4 alkyl, -(CR 8 R 8 ) n -heteroaryl, -(CR 8 R 8 ) n -aryl, -(CR 8 R 8 ) n -cycloalkyl, -(CR 8 R 8 ) n - heterocycloalkyl, CrC4-haloalkyl, halogen, nitro, OR 9 , SR 9 , cyano, C2-C4 alkenyl, C2-C4 alkynyl and NR 9 R 9 .
  • R 3 may be selected from the group comprising: H, C1-C4 alkyl, CrC4-haloalkyl, bromo, cyano, C2-C4 alkenyl and C2-C4 alkynyl.
  • R 3 is independently selected from the group comprising: C1-C4 alkyl, heteroaryl, phenyl, cydoalkyi, heterocycloalkyl, Ci-C4-haloalkyl, halogen, nitro, OR 9 and NR 9 R 9
  • R 3 is independently selected from halo (e.g. bromo) and C1-C4 alkyl.
  • R 3 may be halo (e.g. bromo).
  • R 3 may be C1-C4 alkyl and, more particularly R 3 may be C1-C2 alkyl (e.g. methyl).
  • R 4 is H.
  • R 5 is H. Thus, it may be that X is CH.
  • R 6 and R 7 are H.
  • R 6 and R 7 are not both H .
  • R 6 is selected from -(CR 0 R 0 ) m R 1 1 and C(0)R 12 .
  • R 6 may be independently selected from the group comprising: -C(0)H, -(CR 0 R 0 ) m -Ci-C6 alkyl, -(CR 10 R 10 ) m -heteroaryl, -(CR 10 R 10 ) m -aryl, -(CR 0 R 0 ) m -aryl-Z-A, -(CR 0 R 0 ) m -heteroaryl-Z-A, - (CR 0 R 0 ) m -cycloalkyl, -(CR 0 R 10 ) m -heterocycloalkyl and -(CR 10 R 10 ) m -Ci-C 3 -haloalkyl.
  • R s may be independently selected from the group comprising: -(CR 0 R 0 )m-Ci-Ce alkyl, -(CR 10 R 10 ) m - heteroaryl, -(CR 10 R 10 ) m -aryl, -(CR 10 R 10 ) m -aryl-Z-A, -(CR 10 R 10 ) m -heteroaryl-Z-A, -(CR 10 R 10 ) m - cycloalkyl, -(CR 10 R 0 ) m -heterocycloalkyl and -(CR 10 R 1 0 )m-Ci-C 6 -haloalkyl.
  • R 1 may be selected from: Ci-C 8 alkyl, -(CR 8 R 8 ) P -heteroaryl, -(CR B R 8 ) P -aryl, -(CR 8 R 8 ) P -aryl-Z-A, -(CR 8 R 8 ) P -heteroaryl- Z-A, -(CR 8 R 8 ) P -cycloalkyl, -(CR 8 R 8 ) P -heterocycloalkyl and Ci-Ce-haloalkyl.
  • m is 0.
  • n may be 1.
  • n 1
  • the two R 1 D groups which are attached to the same carbon form an oxo group.
  • -(CR 10 R 10 ) m - may be -C(O)-.
  • R 6 may be -(CR 0 R 10 ) m -aryl, e.g. -(CR 0 R 0 ) m -phenyl.
  • R 6 may be phenyl.
  • Said phenyl group may be substituted or unsubstituted.
  • R B may be a phenyl group substituted with from 1 to 4 substituents selected from halo, C1-C4 alkyl, C1-C4 haloalkyl.
  • R 6 may be a halo, dihalo or trihalo substituted phenyl group, e.g. a 2,5-dihalophenyl group or a 2,6-dihalophenyl group.
  • R 6 may be a phenyl ring to which a heterocyclic ring is fused, e.g. a 1 ,3-
  • R 6 may be .
  • R 6 is unsubstituted phenyl.
  • R 6 may be C(0)R 12 .
  • R 2 may be independently selected from C1-C4 alkyl, C1 -C4 haloalkyl, C3-C5 cycloalkyl.
  • R 12 may be independently selected from Me, Et, i-Pr, CF3 and cyclopropyl.
  • R 12 may be H , i.e R 6 may be C(0)H.
  • R 7 is H.
  • heteroaryl groups may be any aromatic (i.e. a ring system containing 2(n + 1) ⁇ - or n- electrons) 5-10 membered ring system comprising from 1 to 4 heteroatoms independently selected from O, S and N (in other words from 1 to 4 of the atoms forming the ring system are selected from O, S and N).
  • any heteroaryl groups may be independently selected from: 5 membered heteroaryl groups in which the
  • heteroaromatic ring is substituted with 1-4 heteroatoms independently selected from O, S and N; and 6-membered heteroaryl groups in which the heteroaromatic ring is substituted with 1 -3 (e.g.1 -2) nitrogen atoms; 9-membered bicyclic heteroaryl groups in which the heteroaromatic system is substituted with 1-4 heteroatoms independently selected from O, S and N; 10- membered bicyclic heteroaryl groups in which the heteroaromatic system is substituted with 1-4 nitrogen atoms.
  • heteroaryl groups may be independently selected from: pyrrole, furan, thiophene, pyrazole, imidazole, oxazole, isoxazole, triazole, oxadiazole, thiadiazole, tetrazole; pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, isoindole, benzofuran, isobenzofuran, benzothiophene, indazole, benzimidazole, benzoxazole, benzthiazole, benzisoxazole, purine, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, pteridine, phthalazine, naphthyridine.
  • Heteroaryl groups may also be 6-membered heteroaryl groups in which the heteroaromatic ring is substituted with 1 heteroatomic group independently selected from O, S and NH and the ring also comprises a carbonyl group.
  • Such groups include pyridones and pyranones.
  • a heterocycloalkyl group is a 3-8 membered saturated or partially saturated ring comprising 1 or 2 heteroatoms independently selected from O, S and N (in other words from 1 to 4 of the atoms forming the ring system are selected from O, S and N).
  • partially saturated it is meant that the ring may comprise one or two double bonds. This applies particularly to rings with from 5 to 8 members. The double bond will typically be between two carbon atoms but may be between a carbon atom and a nitrogen atom.
  • heterocycloalkyl groups include; piperidine, piperazine, morpholine, thiomorpholine, pyrrolidine, tetrahydrofuran, tetrahydrothiophene, dihydrofuran,
  • a haloalkyi group may have any amount of halogen substituents.
  • the group may contain a single halogen substituent, it may have two or three halogen substituents, or it may be saturated with halogen substituents.
  • any R 1 -R 12 group which contains an aryl or heteroaryl group that aryl or heteroaryl group is optionally substituted, where chemically possible, by 1 to 4 substituents which are each independently selected at each occurrence from the group consisting of: R a ; halo; nitro; cyano; NR a R a ; S0 3 R a ; S0 2 R a ; S0 2 NR a R a ; C0 2 R a ; C(0)R a ; CONR a R a ; CH 2 NR a R a ; CH 2 OR a ; and OR a ; wherein R a is selected from H, C1-C4 alkyl and C1-C4 haloalkyl; and wherein any two substituents on neighbouring atoms and comprising R a groups may join up to form a ring.
  • a group which is represented as SO3R is typically a group having the form S(0) 2 OR.
  • a group which is represented as S0 2 R is typically a group having the form S(0) 2 R.
  • a group which is represented as S0 2 NR a R a is typically a group having the form S(0) 2 NRR.
  • the compounds of the invention may be obtained, stored and/or used in the form of an agronomically acceptable salt.
  • Suitable salts include, but are not limited to, salts of acceptable inorganic acids such as hydrochloric, sulphuric, phosphoric, nitric, carbonic, boric, sulfamic, and hydrobromic acids, or salts of agronomically acceptable organic acids such as acetic, propionic, butyric, tartaric, maleic, hydroxymaleic, fumaric, malic, citric, lactic, mucic, gluconic, benzoic, succinic, oxalic, phenylacetic, methanesulphonic, toluenesulphonic, benzenesulphonic, salicylic, sulphanilic, aspartic, glutamic, edetic, stearic, palmitic, oleic, lauric, pantothenic, tannic, ascorbic and valeric acids.
  • chiral compounds of the invention may be obtained in enantiomerically-enriched form using chromatography, typically HPLC, on an asymmetric resin with a mobile phase consisting of a hydrocarbon, typically heptane or hexane, containing from 0 to 50% by volume of isopropanol, typically from 2% to 20%, and for specific examples, 0 to 5% by volume of an alkylamine e.g. 0.1 % diethylamine. Concentration of the eluate affords the enriched mixture.
  • the racemate (or a racemic precursor) may be reacted with a suitable optically active compound, for example, an alcohol, or, in the case where the compound of the invention contains an acidic or basic moiety, a base or acid such as 1-phenylethylamine or tartaric acid.
  • a suitable optically active compound for example, an alcohol, or, in the case where the compound of the invention contains an acidic or basic moiety, a base or acid such as 1-phenylethylamine or tartaric acid.
  • the resulting diastereomeric mixture may be separated by chromatography and/or fractional crystallization and one or both of the diastereoisomers converted to the corresponding pure enantiomer(s) by means well known to a skilled person.
  • the first type is the racemic compound (true racemate) referred to above wherein one homogeneous form of crystal is produced containing both enantiomers in equimolar amounts.
  • the second type is the racemic mixture or conglomerate wherein two forms of crystal are produced in equimolar amounts each comprising a single enantiomer.
  • Racemic mixtures may be separated by conventional techniques known to those skilled in the art - see, for example, "Stereochemistry of Organic Compounds" by E. L. Eliel and S. H. Wilen (Wiley, 1994).
  • the activity of the compounds of the present invention can be assessed by a variety of in silico, in vitro and in vivo assays. In silico analysis of a variety of compounds has been demonstrated to be predictive of ultimate in vitro and even in vivo activity.
  • the present invention also includes all environmentally acceptable isotopically-labelled compounds of formulae I to VI (including formula la) and their syntheses, wherein one or more atoms are replaced by atoms having the same atomic number, but an atomic mass or mass number different from the atomic mass or mass number usually found in nature.
  • isotopes suitable for inclusion in the compounds of the invention include isotopes of hydrogen, such as 2 H and 3 H, carbon, such as 1 C, 13 C and C, chlorine, such as 36 CI, fluorine, such as 18 F, iodine, such as 123 l and 125 l , nitrogen, such as 13 N and 15 N, oxygen, such as 5 0, 17 0 and 8 0, phosphorus, such as 32 P, and sulphur, such as 35 S.
  • Isotopically-labelled compounds can generally be prepared by conventional techniques known to those skilled in the art or by processes analogous to those described using an appropriate isotopically-labelled reagent in place of the non-labelled reagent previously employed.
  • the compounds of the invention can, at certain concentrations or application rates, be used as fungicides, insecticides, acaricides and nematicides.
  • a method for controlling nematodes, insect or aracnid pests and/or fungal diseases comprising applying an agronomically effective and substantially non-phytotoxic (to the crop plant) quantity of a compound of the invention to the seeds of the plants, to the plants themselves or to the area where it is intended that the plants will grow.
  • the pesticide may be applied as a seed treatment, foliar application, stem application, drench or drip application (chemigation) to the seed, the plant or to the fruit of the plant or to soil or to inert substrate (e.g. inorganic substrates like sand, rockwool, glasswool; expanded minerals like perlite, vermiculite, zeolite or expanded clay), Pumbe, Pyroclastic materials or stuff, synthetic organic substrates (e.g. polyurethane) organic substrates (e.g. peat, composts, tree waste products like coir, wood fibre or chips, tree bark) or to a liquid substrate (e.g. floating hydroponic systems, Nutrient Film Technique, Aeroponics).
  • inert substrate e.g. inorganic substrates like sand, rockwool, glasswool; expanded minerals like perlite, vermiculite, zeolite or expanded clay
  • synthetic organic substrates e.g. polyurethane
  • organic substrates e.g. peat
  • the present invention also relates to a nematicidal, fungicidal, acaricidal and/or insecticidal composition
  • a nematicidal, fungicidal, acaricidal and/or insecticidal composition comprising an effective and non-phytotoxic amount of an active compound of the invention.
  • the composition may further comprise one or more additional nematicides, fungicides, insecticides and/or acaricides.
  • the term "effective and non-phytotoxic amount” means an amount of pesticide according to the invention which is sufficient to control or destroy any of the targeted pests present or liable to appear in the crops and which does not have any significant detrimental effect on the crops or indeed has a positive effect on plant vigour and yield in the absence of target organism.
  • the amount will vary depending on the pest to be controlled, the type of crop, the climatic conditions and the compounds included in the pesticidal composition. This amount can be determined by systematic field trials, which are within the capabilities of a person skilled in the art.
  • the active compounds of the invention can be formulated as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, microencapsulations in polymeric substances and in coating materials for seed, and also as ULV cold and warm fogging formulations.
  • the active compounds can be used neat, or in the form of a formulation, e.g. ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural substances impregnated with active compound, synthetic substances impregnated with active compound, fertilizers and also microencapsulations in polymeric substances.
  • Application may be carried out, for example, by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading, etc. It is also possible to apply the active compounds by the ultra-low volume method or to inject the preparation of active compound or the active compound itself into the soil. It is also possible to treat the seed of the plants.
  • Formulations containing the compounds of the invention are produced in a known manner, for example by mixing the compounds with extenders (e.g. liquid solvents and/or solid carriers), optionally with the use of surfactants (e.g. emulsifiers and/or dispersants and/or foam -formers).
  • extenders e.g. liquid solvents and/or solid carriers
  • surfactants e.g. emulsifiers and/or dispersants and/or foam -formers.
  • the formulations are prepared either in factories/production plants or alternatively before or during the application.
  • auxiliaries are substances which are suitable for imparting to the composition itself and/or to preparations derived therefrom (for example spray liquors, seed dressings) particular properties such as certain technical properties and/or also particular biological properties.
  • suitable auxiliaries are: extenders, solvents and carriers.
  • Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • the alcohols and polyols
  • suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane
  • Suitable solid carriers are: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates;
  • suitable solid carriers for granules are: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic meals, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks;
  • suitable emulsifiers and/or foam-formers are: for example, nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyi sulphates,
  • arylsulphonates and also protein hydrolysates are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP ethers, acid and/or POP-POE esters, alkylaryl and/or POP-POE ethers, fat- and/or POP-POE adducts, POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan- or -sugar adducts, alkyi or aryl sulphates, alkyi- or arylsulphonates and alkyi or aryl phosphates or the corresponding PO-ether adducts.
  • suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP ethers, acid and/or POP-POE esters, alkylaryl and/or POP-POE ethers, fat- and/
  • oligo- or polymers for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly)alcohols or (poly)amines. It is also possible to employ lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and their adducts with formaldehyde.
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
  • Further additives may be mineral and vegetable oils. It is also possible to add colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Other possible additives are perfumes, mineral or vegetable, optionally modified oils and waxes.
  • the formulations may also comprise stabilizers, e.g. low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability.
  • stabilizers e.g. low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability.
  • the formulations generally comprise between 0.01 and 98% by weight of active compound, preferably between 0.1 and 95% and particularly preferably between 0.5 and 90%.
  • the active compounds of the invention can also be used as a mixture with other known nematicides, fungicides, insecticides and/or acaricides, for example, to improve the activity spectrum or to reduce or slow the development of resistance.
  • a mixture with other known active compounds such as herbicides or bactericides, or with fertilizers and growth regulators, safeners or semiochemicals is also possible.
  • Exemplary application rates of the active compounds according to the invention are: when treating leaves: from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, particularly preferably from 50 to 300 g/ha (when the application is carried out by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rock wool or perlite are used); when treating seed: from 2 to 200 g per 100 kg of seed, preferably from 2.5 to 150 g per 100 kg of seed, and particularly preferably from 2.5 to 25 g per 100 kg of seed, very particularly preferably from 2.5 to 12.5 g per 100 kg of seed; when treating the soil: from 0.1 to 10 000 g/ha, preferably from 1 to 5000 g/ha.
  • a formulation which could be used to administer the compounds, particularly in the context of testing for activity, would be to supply all compounds as a 10% solution in DMSO. If there are solubility problems this can be helped by adding acetone (e.g. to dilute a DMSO
  • compositions according to the invention are suitable for protecting any plant variety which is employed in agriculture, in the greenhouse, in forests or in horticulture and, in particular, cereals (e.g. wheat, barley, rye, millet and oats), maize, cotton, soya beans, rice, potatoes, sunflowers, beans, coffee, beet (for example sugar beet and fodder beet), peanuts, vegetables (e.g. tomatoes, cucumbers, onions and lettuce), lawns, fruit and nut trees (e.g. apples pears peaches nectarines, apricots, hazelnut, pecan, macadamia, pistachio), soft fruit (e.g.
  • the active compounds of the invention in combination with good plant tolerance and favourable toxicity to warm-blooded animals and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling pests, in particular nematodes, insects, aracnids and fungal diseases which are encountered in agriculture, in horticulture, in animal husbandry, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector. They may be preferably employed as crop protection agents.
  • the compounds of the invention have activity as insecticides/acaricides.
  • insects may be active against normally sensitive and resistant species of pests and against all or some stages of development.
  • Trichodectes spp from the class of the Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp. , Eriophyes spp., Hemitarsonemus spp.
  • Hyalomma spp. Ixodes spp., Latrodectus mactans, etatetranychus spp. , Oligonychus spp. , Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici; from the class of the Bivalva, for example, Dreissena spp; from the order of the Chilopoda, for example, Geophilus spp.
  • Scutigera spp from the order of the Coleoptera, for example, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.
  • Sphenophorus spp. Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp. , Xylotrechus spp. , Zabrus spp; from the order of the Collembola, for example, Onychiurus armatus; from the order of the Dermaptera, for example, Forficula auricularia; from the order of the Diplopoda, for example, Blaniulus guttulatus; from the order of the Diptera, for example, Aedes spp., Anopheles spp.
  • Bibio hortulanus Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp. , Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp.
  • Biomphalaria spp. Bulinus spp., Deroceras spp., Galba spp. , Lymnaea spp., Oncomelania spp., Succinea spp; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.
  • Ascaris lubricoides Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp.
  • Trichostrongulus spp. Trichuris trichuria, Wuchereria bancrofti.
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with inhibitors which reduce degradation of the active compound after use in the environment of the plant, on the surface of parts of plants or in plant tissues.
  • the active compound content of the use forms prepared from the commercially available formulations can vary within wide limits.
  • the active compound concentration of the use forms can be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1 % by weight.
  • the compounds are employed in a customary manner appropriate for the use forms.
  • the active compounds according to the invention may act not only against plant, hygiene and stored product pests, but also in the veterinary medicine sector against animal parasites (ecto- and endoparasites), such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas.
  • animal parasites ecto- and endoparasites
  • ecto- and endoparasites such as hard ticks, soft ticks, mange mites, leaf mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, feather lice and fleas.
  • insecticidal/acaricidal compounds from the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp. , Phtirus spp., Solenopotes spp; from
  • Amblycerina and Ischnocerina for example, Trimenopon spp. , Menopon spp. , Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. , Felicola spp; diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp. , Anopheles spp., Culex spp. , Simulium spp., Eusimulium spp., Phlebotomus spp. , Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp. ,
  • Haematopota spp. Philipomyia spp., Braula spp. , Musca spp. , Hydrotaea spp. , Stomoxys spp. , Haematobia spp., orellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp.
  • Oestrus spp. Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp; from the order of the Siphonaptrida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp. , Ceratophyllus spp; from the order of the Heteropterida, for example, Cimex spp.
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp. , Demodex spp., Trombicula spp. , Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. , Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp.
  • Each compound of the invention may have activity against one or more than one of the above organisms.
  • the active compounds according to the invention may also be suitable for controlling arthropods which infest agricultural productive livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese and bees, pets, such as, for example, dogs, cats, caged birds and aquarium fish, and also so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice.
  • arthropods which infest agricultural productive livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese and bees, pets, such as, for example, dogs, cats, caged birds and aquarium fish, and also so-called test animals, such as, for example, hamsters, guinea pigs, rats and mice.
  • the insecticidal/acaricidal compounds may be used in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories, by parenteral administration, such as, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal administration, by dermal use in the form, for example, of dipping or bathing, spraying, pouring on and spotting on, washing and powdering, and also with the aid of moulded articles containing the active compound, such as collars, ear marks, tail marks, limb bands, halters, marking devices and the like.
  • enteral administration in the form of, for example, tablets, capsules, potions, drenches, granules, pastes, boluses, the feed-through process and suppositories
  • the insecticidal/acaricidal compounds can be used as formulations (for example powders, emulsions, free-flowing compositions), which comprise the active compounds in an amount of 1 to 80% by weight, directly or after 100- to 10 000-fold dilution, or they can be used as a chemical bath.
  • formulations for example powders, emulsions, free-flowing compositions
  • the active compounds in an amount of 1 to 80% by weight, directly or after 100- to 10 000-fold dilution, or they can be used as a chemical bath.
  • the insecticidal/acaricidal compounds of the invention may be used in the treatment of human disease, particularly parasitic infections e.g. those caused by mites, insects, helminths etc.
  • the invention includes a method of treating a disease (e.g. a parasitic disease), the method comprising administering a therapeutic amount of an antifungal agent of the invention to a subject (e.g. a human subject) in need thereof.
  • the compound may be formulated for topical administration to the infected area of the body or it may be formulated for oral or parenteral administration.
  • the insecticidal/acaricidal compounds may also have activity against insects which destroy industrial materials.
  • Reticulitermes lucifugus Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus
  • Bristletails such as Lepisma saccharina.
  • Each compound of the invention may have activity against one or more than one of the above organisms.
  • Industrial materials in the present connection are to be understood as meaning non-living materials, such as, preferably, plastics, adhesives, sizes, papers and cardboards, leather, wood and processed wood products and coating compositions.
  • insecticidal/acaricidal compounds may also be suitable for controlling animal pests, in particular insects, arachnids and mites, which are found in enclosed spaces, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed alone or in combination with other active compounds and auxiliaries in domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages.
  • insects that may be controlled by insecticidal/acaricidal compounds: from the order of the Scorpionidea, for example, Buthus occitanus; from the order of the Acarina, for example, Argas persicus, Argas reflexus, Bryobia ssp. , Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus,
  • Araneidae from the order of the Opiliones, for example, Pseudoscorpiones chelifer,
  • Attagenus spp. Dermestes spp. , Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum; from the order of the Diptera, for example, Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp.
  • Fannia canicularis usca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa; from the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea doacella, Tinea pellionella, Tineola bisselliella; from the order of the Siphonaptera, for example, Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum; from the order of
  • neonicotinoids growth regulators or active compounds from other known classes of insecticides. They are used in aerosols, pressure-free spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for spreading or in bait stations.
  • aerosols pressure-free spray products
  • pressure-free spray products for example pump and atomizer sprays
  • automatic fogging systems foggers
  • foams foams
  • gels evaporator products with evaporator tablets made of cellulose or polymer
  • liquid evaporators gel and membrane evaporators
  • propeller-driven evaporators propeller-driven evaporators
  • energy-free propeller-driven evapor
  • the compounds of the invention have activity as fungicides.
  • Powdery mildew diseases such as: Blumeria diseases, caused for example by Blumeria graminis; Podosphaera diseases, caused for example by Podosphaera leucotheca;
  • Sphaerotheca diseases caused for example by Sphaerotheca fuliginea
  • Uncinula diseases caused for example by Uncinula necator
  • Rust diseases such as: Gymnosporangium diseases, caused for example by
  • Gymnosporangium sabinae Gymnosporangium sabinae; Hemileia diseases, caused for example by Hemileia vastatix; Phakopsora diseases, caused for example by Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia diseases, caused for example by Puccinia recondita; Uromyces diseases, caused for example by Uromyces appendiculatus;
  • Oomycete diseases such as: Albugo diseases caused for example by Albugo Candida;
  • Bremia diseases caused for example by Bremia lactucae
  • Peronospora diseases caused for example by Peronospora pisi or P. brassicae
  • Phytophthora diseases caused for example by Phytophthora infestans
  • Plasmopara diseases caused for example by Plasmopara viticola
  • Pseudoperonospora diseases caused for example by Pseudoperonospora humuli or
  • Pseudoperonospora cubensis Pythium diseases, caused for example by Pythium ultimum
  • Leafspot, leaf blotch and leaf blight diseases such as: Alternaria diseases, caused for example by Alternaria solani; Cercospora diseases, caused for example by Cercospora beticola;
  • Cladiosporum diseases caused for example by Cladiosporium cucumerinum
  • Cochliobolus diseases caused for example by Cochliobolus sativus
  • Colletotrichum diseases caused for example by Colletotrichum lindemuthanium
  • Cycloconium diseases caused for example by Cycloconium oleaginum
  • Diaporthe diseases caused for example by Diaporthe citri;
  • Drechslera Syn: Helminthosporium) or Cochliobolus miyabeanus; Elsinoe diseases, caused for example by Elsinoe fawcettii; Gloeosporium diseases, caused for example by Gloeosporium laeticolor; Glomerella diseases, caused for example by Glomerella cingulata; Guignardia diseases, caused for example by Guignardia bidwelli; Leptosphaeria diseases, caused for example by Leptosphaeria maculans; Leptosphaeria nodorum; Magnaporthe diseases, caused for example by Magnaporthe grisea; Mycosphaerella diseases, caused for example by Mycosphaerella graminicola; Mycosphaerella arachidtola; Mycosphaerella fibensis;
  • Phaeosphaeria diseases caused for example by Phaeosphaera nodorum
  • Pyrenophora diseases caused for example by Pyrenophora teres
  • Ramularia diseases caused for example by Ramularia collo-cygni
  • Rhynchosporium diseases caused for example by Rhynchosporium secalis
  • Septoria diseases caused for example by Septoria apii or Septoria lycopercisi
  • Typhula diseases caused for example by Typhula incarnata
  • Venturia diseases caused for example by Venturia inaequalis
  • Root and stem diseases such as: Corticium diseases, caused for example by Corticium graminearum; Fusarium diseases, caused for example by Fusa[eta]um oxysporum;
  • Gaeumannomyces diseases caused for example by Gaeumannomyces graminis; Rhizoctonia diseases, caused for example by Rhizoctonia solani; Sarocladium diseases caused for example by Sarocladium oryzae; Sclerotium diseases caused for example by Sclerotium oryzae; Tapesia diseases, caused for example by Tapesia acuformis; Thielavbpsis diseases, caused for example by Thielaviopsis basicola;
  • Ear and panicle diseases including maize cob, such as: Alternaria diseases, caused for example by Alternaria spp.; Aspergillus diseases, caused for example by Aspergillus flavus; Cladosporium diseases, caused for example by Cladosporium spp.; Claviceps diseases, caused for example by Claviceps purpurea; Fusarium diseases, caused for example by Fusarium culmorum; Gibberella diseases, caused for example by Gibberella zeae;
  • Monographella diseases caused for example by Monographella nivalis
  • Smut and bunt diseases such as: Sphacelotheca diseases, caused for example by
  • Tilletia diseases caused for example by Tilletia caries
  • Urocystis diseases caused for example by Urocystis occulta
  • Ustilago diseases caused for example by Ustilago nuda
  • Fruit rot and mould diseases such as: Aspergillus diseases, caused for example by Aspergillus flavus; Botrytis diseases, caused for example by Botrytis cinerea; Penicillium diseases, caused for example by Penicillium expansum; Rhizopus diseases caused by example by Rhizopus stolonifer; Sclerotinia diseases, caused for example by Sclerotinia sclerotiorum;
  • Verticilium diseases caused for example by Verticilium alboatrum
  • Seed and soil borne decay, mould, wilt, rot and dampingoff diseases such as: Alternaria diseases, caused for example by Alternaria brassicicola; Aphanomyces diseases, caused for example by Aphanomyces euteiches; Ascochyta diseases, caused for example by Ascochyta lentis Aspergillus diseases, caused for example by Aspergillus flavus; Cladosporium diseases, caused for example by Cladosporium herbarum; Cochliobolus diseases, caused for example by Cochliobolus sativus (Conidiaform: Drechslera, Bipolaris Syn: Helminthosporium);
  • Colletotrichum diseases caused for example by Colletotrichum coccodes; Fusarium diseases, caused for example by Fusarium culmorum; Gibberella diseases, caused for example by Gibberella zeae; Macrophomina diseases, caused for example by Macrophomina phaseolina Monographella diseases, caused for example by onographella nivalis; Penicillium diseases, caused for example by Penicillium expansum; Phoma diseases, caused for example by Phoma lingam; Phomopsis diseases, caused for example by Phomopsis sojae; Phytophthora diseases, caused for example by Phytophthora cactorum; Pyrenophora diseases, caused for example by Pyrenophora graminea Pyricularia diseases, caused for example by Pyricularia oryzae; Pythium diseases, caused for example by Pythium ultimum; hizoctonia diseases, caused for example by Rhizoctonia solani; Rhizopus diseases, caused for example by Rhizopus
  • Canker, broom and dieback diseases such as: Nectria diseases, caused for example by Nectria galligena;
  • Blight diseases such as:
  • Leaf blister or leaf curl diseases such as: Exobasidium diseases caused for example by Exobasidium vexans; Taphrina diseases, caused for example by Taphrina deformans; - Decline diseases of wooden plants such as:
  • Esca diseases caused for example by Phaemoniella clamydospora, Phaeomoniella clamydospora, Phaeoacremonium aleophilum and Fomitiporia mediterranea;
  • Eutypa dyeback caused for example by Eutypa lata
  • Dutch elm disease caused for example by Ceratocystsc ulmi
  • Ganoderma diseases caused by example by Ganoderma boninense
  • Botrytis diseases caused for example by Botrytis cinerea
  • Rhizoctonia diseases caused for example by Rhizoctonia solani
  • Helminthosporium diseases caused for example by Helminthospohum solani
  • Rhizoctonia diseases caused for example by Rhizoctonia solani
  • Helminthosporium diseases caused for example by Helminthospohum solani
  • Plasmodiophora diseases caused for example by Plamodiophora brassicae.
  • the compounds of the invention may be active against a broad spectrum of fungal diseases. Alternatively they may be active specifically against cereal fungal diseases or they may be specifically active against oomycete diseases. Notable cereal fungal diseases are:
  • the compounds of the invention may also have some activity against other microbes, e.g. bacteria.
  • the fungicidal compounds of the invention may also be used in the treatment of fungal diseases of humans and animals (e.g. mammals). Likewise, the bactericidal compounds of the invention may be used in the treatment of bacterial diseases of humans and animals.
  • the invention includes a method of treating a fungal or bacterial disease, the method comprising administering a therapeutic amount of an antifungal agent of the invention to a subject (e.g. a human subject) in need thereof.
  • the compound may be formulated for topical administration to the infected area of the body or it may be formulated for oral or parenteral administration.
  • active compound 1 part by weight of active compound is mixed with 24.5 parts by weight of acetone, 24.5 parts by weight of ⁇ , ⁇ -dimethylacetamide and 1 part by weight of alkylaryl polyglycol ether, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the formulation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab (Venturia inaequalis) and then remain for 1 day in an incubation cabinet at approximately 20 °C and a relative atmospheric humidity of 100%. The plants are then placed in a greenhouse at approximately 21 °C and a relative atmospheric humidity of approximately 90%. The test is evaluated 10 days after the inoculation.
  • active compound 1 part by weight of active compound is mixed with 24.5 parts by weight of acetone, 24.5 parts by weight of ⁇ , ⁇ -dimethylacetamide and 1 part by weight of alkylaryl polyglycol ether, and the concentrate is diluted with water to the desired concentration.
  • active compound 1 part by weight of active compound is mixed with 24.5 parts by weight of acetone, 24.5 parts by weight of ⁇ , ⁇ -dimethylacetamide and 1 part by weight of alkylaryl polyglycol ether, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the formulation of active compound. After the spray coating has dried on, 2 small pieces of agar covered with growth of Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at 20 °C and a relative atmospheric humidity of 100%. 2 days after the inoculation, the size of the lesions on the leaves is evaluated.
  • active compound 1 part by weight of active compound is mixed with 49 parts by weight of DMF and 1 part by weight of alkylarylpolyglycolether, and the concentrate is diluted with water to the desired concentration.
  • active compound 1 part by weight of active compound is mixed with 49 parts by weight of DMF and 1 part by weight of alkylarylpolyglycolether, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the formulation of active compound at the stated rate of application.
  • the plants are inoculated with an aqueous spore suspension of
  • a suitable formulation of active compound 1 part by weight of active compound or the compound combination is mixed with 50 parts by weight of ⁇ , ⁇ -dimethylacetamide and 1 part by weight of alkylaryl polyglycol ether, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with a formulation of active compound or active compound combination at the stated rate of application. After the spray coating has dried on, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabinet at 20 °C and a relative atmospheric humidity of 100%.
  • the plants are placed in a greenhouse at a temperature of approximately 15 °C and a relative atmospheric humidity of approximately 80%.
  • the test is evaluated 10 days after the inoculation.
  • active compound 1 part by weight of active compound or the compound combination is mixed with 50 parts by weight of N ,N-dimethylacetamide and 1 part by weight of alkylaryl polyglycol ether, and the concentrate is diluted with water to the desired concentration.
  • active compound 1 part by weight of active compound or the compound combination is mixed with 50 parts by weight of N ,N-dimethylacetamide and 1 part by weight of alkylaryl polyglycol ether, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with a formulation of active compound at the stated rate of application. After the spray coating has dried on, the plants are sprayed with a conidia suspension of Pyrenophora teres. The plants remain for 48 hours in an incubation cabinet at 20 °C and a relative atmospheric humidity of 100%.
  • the plants are placed in a greenhouse at a temperature of approximately 20 °C and a relative atmospheric humidity of approximately 80%.
  • the test is evaluated 10 days after the inoculation.
  • active compound 1 part by weight of active compound is mixed with 28.5 parts by weight of acetone and 1.5 parts by weight of polyoxyethylene alkyl phenyl ether, and the concentrate is diluted with water to the desired concentration.
  • active compound 1 part by weight of active compound is mixed with 28.5 parts by weight of acetone and 1.5 parts by weight of polyoxyethylene alkyl phenyl ether, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the formulation of active compound at the stated rate of application.
  • the plants are inoculated with an aqueous spore suspension of the causal agent of rice blast Pyricularia oryzae.
  • the plants are then placed in an incubator at approximately 25 °C and a relative atmospheric humidity of approximately 100% for 1 day.
  • the test is evaluated 7 days after the inoculation.
  • active compound 1 part by weight of active compound is mixed with 28.5 parts by weight of acetone and 1.5 parts by weight of polyoxyethylene alkyl phenyl ether, and the concentrate is diluted with water to the desired concentration.
  • active compound 1 part by weight of active compound is mixed with 28.5 parts by weight of acetone and 1.5 parts by weight of polyoxyethylene alkyl phenyl ether, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the formulation of active compound at the stated rate of application.
  • the plants are inoculated with a hypha of the causal agent of rice sheath blight Rhizoctonia solani.
  • the plants are then placed in an incubator at approximately 25 °C and a relative atmospheric humidity of approximately 100%.
  • active compound 1 part by weight of active compound is mixed with 28.5 parts by weight of acetone and 1.5 parts by weight of polyoxyethylene alkyl phenyl ether, and the concentrate is diluted with water to the desired concentration.
  • active compound 1 part by weight of active compound is mixed with 28.5 parts by weight of acetone and 1.5 parts by weight of polyoxyethylene alkyl phenyl ether, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the formulation of active compound at the stated rate of application.
  • the plants are inoculated with an aqueous spore suspension of the causal agent of rice brown spot Cochliobolus miyabeanus.
  • the plants are then placed in an incubator at approximately 25 °C and a relative atmospheric humidity of approximately 100% for 1 day.
  • the test is evaluated 4 days after the inoculation.
  • the compounds of the invention can be used as nematicides.
  • Phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp.,
  • Heliocotylenchus spp. Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • active compound 1 part by weight of active compound is mixed with 80.0 parts by weight of acetone, and the concentrate is diluted with emulsifier- containing water to the desired concentration. Vessels are filled with sand, a solution of the active ingredient, a suspension containing eggs and larvae of Meloidogyne incognita and lettuce seeds. The lettuce seeds germinate and the seedlings grow. Galls develop in the roots. After 14 days the nematicidal activity is determined on the basis of the percentage of gall formation.
  • Sensitive functional groups may need to be protected and deprotected during synthesis of a compound of the invention. This may be achieved by conventional methods, for example as described in "Protective Groups in Organic Synthesis” by TW Greene and PGM Wuts, John Wiley & Sons Inc (1999), and references therein.
  • a typical synthesis starts from an appropriately substituted pyridinyl or pyrimidinyl acid.
  • the starting material is not commercially available, the range of methods available for the synthesis of polysubstituted pyridines and pyrimidines is well known to those skilled in the art.
  • the amide coupling to form amide C can be achieved using any conventional means.
  • One method would be by mixing acid A with amine B in the presence of an activating agent (e.g. DCC) and a nucleophilic catalyst (e.g. D AP).
  • an activating agent e.g. DCC
  • a nucleophilic catalyst e.g. D AP
  • a mixed anhydride using e.g. EtOCOCI and NEt 3 at 0 °C
  • the amine coupling step can be achieved by mixing amide C with amine D.
  • Exemplary reaction conditions for this coupling step is to perform the reaction in a dioxane/water mixture optionally in the presence of CuS0 4 (the presence of the CuS0 is preferred for instances in which Hal is Br or I) at 80 °C.
  • a typical synthesis starts from an appropriately substituted pyridinyl or pyrimidinyl acid F.
  • Amide coupling and amine addition steps are then performed similarly to the corresponding steps described for Scheme 1 above.
  • the pyridine or pyrimidine ring can then be deprotonated using a base (e.g. LDA in THF and hexane at -70 °C) and alkylated with alkylating agent J (e.g. at -70 °C)
  • Flash chromatography was carried out using silica gel (40-63 ⁇ particles). Thin layer chromatography was carried out on pre-coated aluminium backed plates (Merck silica Keiselgel 60 F254) . Visualisation was carried out with UV light (254 nm) and by staining with either potassium permanganate, phosphomolybdic acid (PMA) or ninhydrin solutions. Where hexane is specified as a flash chromatography solvent, petroleum ether (b.p. 40-60 °C) can be used as an alternative.
  • ESI mass spectrometry was performed using a Bruker HCT Ultra LCMS instrument (Agilent 1200 Series LC with diode array detector and Bruker HCT Ultra Ion Trap MS) using a
  • reaction was stirred at room temperature for 10 minutes before a solution of omethylbenzylamine (0.17 mL, 1.32 mmol) in DCM (4 mL) was added and stirring was continued for 20 h, after which time TLC showed complete consumption of the starting material.
  • the reaction mixture was quenched with 2M HCI ⁇ (5 mL) and water (10 mL) then extracted with EtOAc (3 x 25 mL) before the organics were washed with brine (2 x 25 mL), dried over MgSCU and the solvent removed in vacuo.
  • the crude material was purified by flash chromatography on silica gel (solvent 30% EtOAc/hexane) to afford the title compound as a white solid (160 mg, 55%).
  • reaction mixture was quenched with 2M HCI(ag) (5 mL) and water (10 mL) then extracted with EtOAc (3 x 25 mL) before the organics were washed with brine (2 x 25 mL), dried over MgSC and the solvent removed in vacuo.
  • the crude material was purified by flash chromatography on silica gel (solvent 70% hexane/EtOAc) to afford the title compound as a yellow oil (174 mg, 43%).
  • 6-Chloro-N-c clopentyl-3-methyl-pyridine-2-carboxamide 19 /V-Ethyldiisopropylamine (2.28 mL, 13.11 mmol) was added to a suspension of 6-chloro-3- methyl-pyridine-2-carboxylic acid (750 mg, 4.37 mmol), 4-(dimethylamino)pyridine (801 mg, 6.56 mmol) and A/-(3-dimethylaminopropyl)-A/'-ethylcarbodiimide hydrochloride (1.26 g, 6.56 mmol) in DCM (10 mL).
  • reaction mixture was quenched with sat N ⁇ CI ⁇ ) (5 mL) and water (10 mL) then extracted with EtOAc (3 x 25 mL) before the organics were washed with brine (2 x 25 mL), dried over MgSC and the solvent removed in vacuo.
  • the crude material was purified by flash chromatography on silica gel (solvent 75% hexane/EtOAc) to afford the title compound as a white solid (142 mg, 61%).
  • dichloromethane (20 ml_) before triethylamine (0.73 g, 1.0 ml_, 7.25 mmol) and a- methylbenzylamine (422 mg, 443 ⁇ , 3.48 mmol) were added dropwise and the mixture was stirred at room temperature for 1.5 h.
  • the mixture was diluted with dichloromethane (30 mL), washed with sat. aqueous sodium bicarbonate (50 mL), 0.1 M hydrochloric acid (50 mL), dried over MgSCU and the solvent removed in vacuo to afford the title compound as a pale brown oil that crystallised on standing (0.59 g, 73 %).
  • Compound 31 is a compound of the prior art (WO2010/012793) and is included for reference purposes only.
  • Example 2 Testing the insecticidal and acaricidal activity of compounds of the invention.
  • a laboratory bioassay can be conducted to screen the compounds of the invention for biocidal activity against target species (examples might be: aphids (Myzus persicae), mosquito larvae (Aedes aegypti) cabbage moth larvae (Mamestra brassicae), and two-spotted spider mites ( Tetranychus urticae), in terms of knockdown and mortality.
  • Target species examples might be: aphids (Myzus persicae), mosquito larvae (Aedes aegypti) cabbage moth larvae (Mamestra brassicae), and two-spotted spider mites ( Tetranychus urticae), in terms of knockdown and mortality.
  • Compounds are diluted in DMSO containing 1 % Tween (the Tween is optional but has been used for testing the compounds of the invention) and assessed at a range of concentrations (e.g. from 0.5% to 0.00001%).
  • a DMSO only negative control is also included
  • Aphids, Myzus persicae, can be maintained on Chinese cabbage plants. Mixed sex and age aphids are used in the experiments.
  • Mosquitoes Aedes aegypti
  • Aedes aegypti can be obtained as eggs and reared to 3 rd instar larvae, prior to use in the experiments.
  • Cabbage moths Mamestra brassicae
  • Cabbage moths Mamestra brassicae
  • Lacanobia oleracea caterpillars can also be used.
  • Two-spotted spider mites Tetranychus urticae, can be obtained from a standard susceptible laboratory culture. Mixed sex and age mites are used in the experiments.
  • the temperature should be maintained between about 22 °C and about 25 °C and the relative humidity should range from about 25 % to about 45%.
  • Arthropods are maintained on a 16:8 hour (light: dark) photoperiod post treatment.
  • test compounds are dissolved in DMSO and diluted at a range of six concentrations (e.g.
  • the targets are counted into a 55 mm diameter Petri dish lined with a leaf disc (abaxial surface upwards) mounted on damp cotton wool.
  • leaf discs should be cut from round cabbage, for mites, leaf discs should be cut from dwarf French bean plants.
  • Mosquito larvae should be placed into an 11 cm diameter plastic container, filled with approximately 150 ml of de-chlorinated tap water, using a pipette.
  • the targets are sprayed using the Potter tower or in the case of mosquito larvae, a Gilson pipette.
  • the number of knocked down and dead insects or arthropods is assessed at 24 and 48 hours post treatment.
  • a number of compounds of the invention achieved excellent control over spider mites. Indeed, compounds 11 , 30, 24, 20 and 28 were considerably more active against spider mites than the reference compound 31. Compound 20 also achieved greater than 50% control over both aphids and caterpillars at the highest concentrations tested, again better than the reference compound 31 .
  • the fungicidal activity of the compounds of the invention was tested against a range of fungal plant pathogens. ECso were determined for each fungicide tested by measuring the Optical Density at 590 nm of each well of the microtitre plate after 3 days of incubation (F.
  • a compound for which an EC50 could not be determined for that pathogen (because the percentage of inhibition obtained at the highest concentration of fungicide tested (40 Mg/ml) is lower than 50 %) was not assigned a star rating; a compound having an EC50 between 18 and 40 ⁇ g/ml was assigned a rating of one star; a compound having an EC50 between 5 and 18 pg/ml was assigned a rating of two stars; and a compound having an EC50 below 5 ⁇ g/ml was assigned a rating of three stars.

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  • Chemical & Material Sciences (AREA)
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  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Pest Control & Pesticides (AREA)
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  • Pyridine Compounds (AREA)
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  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des composés qui sont d'utilité dans le domaine de l'agriculture en tant que nématicides, fongicides, insecticides et/ou acaricides. Les composés selon l'invention sont la pyridine ou pyrimidine substituée à la fois par un groupe substituant amine et par un groupe substituant amide. L'invention concerne également des compositions comprenant lesdits composés et des procédés d'utilisation desdits composés.
PCT/GB2014/052841 2013-09-18 2014-09-18 Produits chimiques agricoles WO2015040405A2 (fr)

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Cited By (7)

* Cited by examiner, † Cited by third party
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WO2020239855A1 (fr) 2019-05-29 2020-12-03 Syngenta Crop Protection Ag Dérivés microbiocides
WO2020239853A1 (fr) * 2019-05-29 2020-12-03 Syngenta Crop Protection Ag Dérivés microbiocides
WO2020239854A1 (fr) 2019-05-29 2020-12-03 Syngenta Crop Protection Ag Dérivés microbiocides
WO2020239856A1 (fr) * 2019-05-29 2020-12-03 Syngenta Crop Protection Ag Dérivés microbiocides
CN115246787A (zh) * 2021-04-28 2022-10-28 吉林省达凯生物医药有限公司 间位双取代化合物及其制备和在防治蚊虫、植物病菌病中的应用
WO2023051261A1 (fr) * 2021-09-28 2023-04-06 沈阳中化农药化工研发有限公司 Composé imine et son utilisation
WO2024072794A1 (fr) * 2022-09-26 2024-04-04 Rectify Pharmaceuticals, Inc. Composés de pyridine carboxamide et leur utilisation dans le traitement de pathologies médicales

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JO2308B1 (en) * 1999-05-31 2005-09-12 اف. هوفمان- لاروش أيه جي‏ Derivatives of phenylpyrmidine
GB0219961D0 (en) * 2002-08-28 2002-10-02 Pfizer Ltd Oxytocin inhibitors
US20050176767A1 (en) * 2003-10-30 2005-08-11 Laval Chan Chun Kong Pyridine carboxamide and methods for inhibiting HIV integrase
JP2009209090A (ja) * 2008-03-04 2009-09-17 Mitsui Chemicals Inc 殺虫剤及び該殺虫剤に含まれる化合物、並びに該化合物の使用方法
EP2184273A1 (fr) * 2008-11-05 2010-05-12 Bayer CropScience AG Composés substitués par l'halogène comme pesticides
US8703768B2 (en) * 2010-06-09 2014-04-22 Hoffmann-La Roche Inc. Nitrogen containing heteroaryl compounds
WO2014049488A1 (fr) * 2012-09-28 2014-04-03 Pfizer Inc. Composés de benzamide et hétérobenzamide

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020239855A1 (fr) 2019-05-29 2020-12-03 Syngenta Crop Protection Ag Dérivés microbiocides
WO2020239853A1 (fr) * 2019-05-29 2020-12-03 Syngenta Crop Protection Ag Dérivés microbiocides
WO2020239854A1 (fr) 2019-05-29 2020-12-03 Syngenta Crop Protection Ag Dérivés microbiocides
WO2020239856A1 (fr) * 2019-05-29 2020-12-03 Syngenta Crop Protection Ag Dérivés microbiocides
CN113874353A (zh) * 2019-05-29 2021-12-31 先正达农作物保护股份公司 杀微生物衍生物
CN113906034A (zh) * 2019-05-29 2022-01-07 先正达农作物保护股份公司 杀微生物衍生物
CN113924294A (zh) * 2019-05-29 2022-01-11 先正达农作物保护股份公司 杀微生物衍生物
CN115246787A (zh) * 2021-04-28 2022-10-28 吉林省达凯生物医药有限公司 间位双取代化合物及其制备和在防治蚊虫、植物病菌病中的应用
CN115246787B (zh) * 2021-04-28 2024-03-12 吉林省达凯生物医药有限公司 间位双取代化合物及其制备和在防治蚊虫、植物病菌病中的应用
WO2023051261A1 (fr) * 2021-09-28 2023-04-06 沈阳中化农药化工研发有限公司 Composé imine et son utilisation
WO2024072794A1 (fr) * 2022-09-26 2024-04-04 Rectify Pharmaceuticals, Inc. Composés de pyridine carboxamide et leur utilisation dans le traitement de pathologies médicales

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