WO2013026695A1 - Dérivés d'isoxazoline en tant que composés insecticides - Google Patents

Dérivés d'isoxazoline en tant que composés insecticides Download PDF

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Publication number
WO2013026695A1
WO2013026695A1 PCT/EP2012/065421 EP2012065421W WO2013026695A1 WO 2013026695 A1 WO2013026695 A1 WO 2013026695A1 EP 2012065421 W EP2012065421 W EP 2012065421W WO 2013026695 A1 WO2013026695 A1 WO 2013026695A1
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Prior art keywords
spp
compound
formula
chloro
trifluoromethyl
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PCT/EP2012/065421
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English (en)
Inventor
Jérôme Yves CASSAYRE
Peter Renold
Thomas Pitterna
Myriem El Qacemi
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Syngenta Participations Ag
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Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Priority to KR1020147007321A priority Critical patent/KR20140054302A/ko
Priority to JP2014526519A priority patent/JP6061934B2/ja
Priority to CN201610356475.3A priority patent/CN106045962A/zh
Priority to BR112014004235A priority patent/BR112014004235A2/pt
Priority to AU2012298448A priority patent/AU2012298448A1/en
Priority to CN201280041298.XA priority patent/CN103764644A/zh
Priority to EP12748717.1A priority patent/EP2748155B1/fr
Priority to PCT/EP2012/066554 priority patent/WO2013026931A1/fr
Priority to MX2014002092A priority patent/MX2014002092A/es
Publication of WO2013026695A1 publication Critical patent/WO2013026695A1/fr
Priority to CO14036579A priority patent/CO6890111A2/es
Priority to CL2014000439A priority patent/CL2014000439A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
    • C07D331/04—Four-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
    • A01N43/80—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
    • C07D413/02—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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to certain isoxazolines derivatives, to processes and intermediates for preparing these derivatives, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these derivatives and to methods of using these derivatives to control insect, acarine, nematode and mollusc pests.
  • the present invention also relates to use of these compounds in the field of animal health.
  • the present invention provides compounds of formula I
  • G 1 is oxygen
  • R 1 is hydrogen
  • L is a bond, methylene or ethylene
  • a 1 and A 2 is S, SO or S0 2 and the other is -C(R 4 )R 4 -;
  • R 3 is hydrogen or methyl
  • each R 4 is independently hydrogen or methyl
  • Y 1 , Y 2 and Y 3 are independently CH or nitrogen;
  • R 5 is bromo, chloro, fluoro
  • X 2 is C-X 6 or nitrogen
  • ⁇ ', ⁇ 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X 1 , X 3 and X 6 are not hydrogen;
  • X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
  • the compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds. The invention also covers salts and N-oxides of the compounds of the invention.
  • the compounds of the invention may contain one or more asymmetric carbon atoms, and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
  • Alkyl groups can be in the form of a straight or branched chain and are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl, 2 -methyl-prop -1-yl or 2-methyl-prop-2- yl.
  • the alkyl groups are preferably Ci-C 6 , more preferably Q-C4, most preferably Q-C 3 alkyl groups. Where an alkyl moiety is said to be substituted, the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Alkylene groups can be in the form of a straight or branched chain and are, for example, -CH 2 -, -CH 2 -CH 2 -, -CH(CH 3 )-, -CH 2 -CH 2 -CH 2 -, -CH(CH 3 )-CH 2 -, or -CH(CH 2 CH 3 )-.
  • the alkylene groups are preferably C 1 -C3, more preferably C r C 2 , most preferably Q alkylene groups.
  • Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z) -configuration. Examples are vinyl and allyl.
  • the alkenyl groups are preferably C 2 -C 6 , more preferably C 2 -C 4 , most preferably C 2 -C 3 alkenyl groups.
  • Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl.
  • the alkynyl groups are preferably C 2 -C6, more preferably C 2 -C4, most preferably C 2 -C 3 alkynyl groups.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl groups are alkyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, difluoromethyl, trifluoromethyl,
  • Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or 1 ,2-dichloro-2-fluoro-vinyl.
  • Haloalkynyl groups are alkynyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, l-chloro-prop-2-ynyl.
  • Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic form and are, for example, cyclopropyl, cyclobutyl, cyclohexyl and bicyclo[2.2.1]heptan-2-yl.
  • the cycloalkyl groups are preferably C 3 -C 8 , more preferably C 3 -C 6 cycloalkyl groups.
  • the cycloalkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Aryl groups are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heteroaryl groups are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings.
  • single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur.
  • monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g.
  • bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl.
  • Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Heterocyclyl groups or heterocyclic rings are defined to include heteroaryl groups and in addition their unsaturated or partially unsaturated analogues.
  • monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, [l,3]dioxolanyl, piperidinyl, piperazinyl, [l,4]dioxanyl, and morpholinyl or their oxidised versions such as 1 -oxo-thietanyl and 1,1-dioxo-thietanyl.
  • bicyclic groups examples include 2,3-dihydro-benzofuranyl, benzo[l,4]dioxolanyl, benzo[l,3]dioxolanyl, chromenyl, and 2,3- dihydro-benzo[l,4]dioxinyl.
  • a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 , X 4 , X 5 and X 6 for compounds of formula I are, in any combination, as set out below.
  • R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-Dioxo-thietan-3-yl-, 2,2-dimethylthietan-3- yl-, 2,2-dimethyl-l-oxo-thietan-3-yl-, 2,2-dimethyl-l,l -Dioxo-thietan-3-yl-, 3 -Methyl -thietan-3-yl-, 3- Methyl- 1 -oxo-thietan-3 -yl-, 3 -Methyl- 1 , 1 -Dioxo-thietan-3 -yl-, thietan-3 -ylmethyl-, 1 -oxo-thietan-3 - ylmethyl-, 1,1 -Dioxo-thietan-3 -ylmethyl-, thietan-2
  • R 2 is thietan-3 -yl-, 1-oxo- thietan-3-yl-, 1,1 -Dioxo-thietan-3 -yl-, thietan-3 -ylmethyl-, 1 -oxo-thietan-3 -ylmethyl-, or 1,1 -Dioxo- thietan-3 -ylmethyl-, most preferably thietan-3 -yl-, 1 -oxo-thietan-3 -yl-, or 1,1 -Dioxo-thietan-3 -yl-.
  • Y 1 is CH, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is CH, Y 3 is N. More preferably Y 1 is CH, Y 2 is CH, Y 3 is CH.
  • X is chloro
  • X is CH
  • X is chloro
  • X is chloro
  • X is C-F
  • X is hydrogen
  • X is hydrogen
  • X 1 is chloro, X 2 is N, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl.
  • X 1 is chloro, X 2 is CH, X 3 is chloro, or X 1 is chloro, X 2 is C-Cl, X 3 is chloro, or X 1 is chloro, X 2 is C-F, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl.
  • X 1 is chloro, X 2 is CH, X 3 is chloro.
  • X 4 is trifluoromethyl.
  • the invention provides compounds of formula I wherein R 5 is chloro and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
  • the invention provides compounds of formula I wherein R 5 is bromo and G 1 , R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
  • the invention provides compounds of formula I wherein R 5 is fluoro and G 1 ,
  • R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I.
  • G 1 is oxygen
  • R 1 is hydrogen
  • R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-Dioxo-thietan-3-yl-, thietan-3-ylmethyl-, 1-oxo- thietan-3-ylmethyl-, or l,l-Dioxo-thietan-3-ylmethyl-;
  • Y 1 is CH, Y 2 is CH, Y 3 is CH;
  • R 5 is bromo, chloro, fluoro
  • X 1 is chloro, X 2 is CH, X 3 is chloro, or X 1 is chloro, X 2 is C-Cl, X 3 is chloro, or X 1 is chloro, X 2 is C-F, X 3 is chloro, orX 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl;
  • X 4 is trifluoromethyl.
  • G 1 is oxygen
  • R 1 is hydrogen
  • R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l-Dioxo-thietan-3-yl-;
  • Y 1 is CH, Y 2 is CH, Y 3 is CH;
  • R 5 is chloro
  • X 1 is chloro, X 2 is CH, X 3 is chloro, X 1 is chloro, X 2 is C-Cl, X 3 is chloro, X 1 is chloro, X 2 is C-F, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl;
  • X 4 is trifluoromethyl.
  • the compound of formula I is not be a compound wherein R 2 is thietan-3-yl-, 1-oxo- thietan-3-yl-, l,l-Dioxo-thietan-3-yl-, 3-Methyl-thietan-3-yl-, thietan-3-ylmethyl-, l-oxo-thietan-3- ylmethyl-, l,l-Dioxo-thietan-3-ylmethyl-, thietan-2-ylmethyl-, (l-oxothietan-2-yl)methyl-, (1,1- dioxothietan-2-yl)methyl-, 2-(thietan-3-yl)ethanyl, 2-(l,l-dioxothietan-3-yl)ethanyl, or 2-(l -oxothietan-3- yl)ethanyl, Y 1
  • the invention provides a method of controlling insects, acarines, nematodes or molluscs, preferably in a crop of useful plants, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I as defined above, including preferences thereof.
  • the invention provides a method of protecting useful plants from insects, acarines, nematodes or molluscs, comprising applying to said plants, to the locus thereof, or to plant propagation material thereof, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula I as defined above, including preferences thereof.
  • the compound of formula I is a compound wherein R 2 is thietan-3-yl-, 1 -oxo- thietan-3-yl-, l,l -Dioxo-thietan-3-yl-, 3-Methyl-thietan-3-yl-, thietan-3-ylmethyl-, l-oxo-thietan-3- ylmethyl-, l,l -Dioxo-thietan-3-ylmethyl-, thietan-2-ylmethyl-, (l -oxothietan-2-yl)methyl-, (1,1 - dioxothietan-2-yl)methyl-, 2-(thietan-3-yl)ethanyl, 2-(l,l-dioxothietan-3-yl)ethanyl, or 2-(l -oxothietan-3- yl)ethanyl,
  • said methods do not comprise applying the compound of formula I to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
  • the invention also relates to the following intermediates which are useful for the preparation of compounds of formula I:
  • G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are as defined for the compound of formula I.
  • Preferred definitions of G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are the same as for the
  • G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are as defined for the compound of formula I.
  • Preferred definitions of G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are the same as for the corresponding substituents of compounds of formula I.
  • G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are as defined for the compound of formula I.
  • Preferred definitions of G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are the same as for the corresponding substituents of compounds of formula I.
  • G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are as defined for the compound of formula I.
  • Preferred definitions of G 1 , R 1 , R 2 , R 5 , X 1 , X 2 , X 3 , X 4 , Y 1 , Y 2 , and Y 3 are the same as for the corresponding substituents of compounds of formula I.
  • Preferred definitions of G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , and Y 3 are the same as for the corresponding substituents of compounds of formula I.
  • Table IP provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 2P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 3 ⁇ provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is fluoro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 4 ⁇ provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 5P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 6P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 7P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 8P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 9P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 10P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X2 is bromo, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table I IP provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 12P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 13P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromehtyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 14P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 15P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-CL, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 16P
  • Table 16P provides 18 compounds of Formula I-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 17P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 18P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 19P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is fluoro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 20P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 21P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 22P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 23P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 24P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 25P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, Xlis fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 26P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X2 is bromo, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 27 ⁇ provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 28 ⁇ provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 29P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromehtyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 30P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 3 IP provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-CL, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 32P provides 18 compounds of Formula XI -A wherein Gl is oxygen, Rl is hydrogen, XI is
  • Table 33P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 34P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 35P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is fluoro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 36P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 37P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 38 ⁇ provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 39 ⁇ provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 40P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 41P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, Xlis fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 42P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X2 is bromo, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 43P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 44P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 45P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromehtyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 46P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 47P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-CL, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 48P provides 18 compounds of Formula X2-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 49P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 50 ⁇ provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 51P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is fluoro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 52P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 53P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 54P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 55P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 56P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 57P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, Xlis fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 58P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X2 is bromo, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 59P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 60P
  • Table 60P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 61P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromehtyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 62P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 63P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-CL, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 64P provides 18 compounds of Formula X3-A wherein Gl is oxygen, Rl is hydrogen, XI is
  • Table 65P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 66P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 67P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is fluoro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 68P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 69P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 70P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 71P
  • Table 71P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 72 ⁇ provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 73P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, Xlis fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 74P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X2 is bromo, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 75P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 76P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 77P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromehtyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 78P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 79P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-CL, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table 80P provides 18 compounds of Formula X4-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table P.
  • Table IX provides 18 compounds of Formula X5-A wherein Gl is oxygen, Rl is hydrogen, Yl is CH, Y2 is CH, Y3 is CH, X5 is chloro, R5 and R2 have the values listed in the Table X.
  • Table 2X provides 18 compounds of Formula X5-A wherein Gl is oxygen, Rl is hydrogen, Yl is CH, Y2 is CH, Y3 is CH, X5 is bromo, R5 and R2 have the values listed in the Table X.
  • Table 3X provides 18 compounds of Formula X5-A wherein Gl is oxygen, Rl is hydrogen, Yl is CH, Y2 is CH, Y3 is CH, X5 is iodo, R5 and R2 have the values listed in the Table X.
  • Table 4X provides 18 compounds of Formula X5-A wherein Gl is oxygen, Rl is hydrogen, Yl is CH, Y2 is CH, Y3 is CH, X5 is amino, R5 and R2 have the values listed in the Table X.
  • Table 5X provides 18 compounds of Formula X5-A wherein Gl is oxygen, Rl is hydrogen, Yl is CH, Y2 is CH, Y3 is CH, X5 is CHO, R5 and R2 have the values listed in the Table X.
  • Table 6X provides 18 compounds of Formula X5-A wherein Gl is oxygen, Rl is hydrogen, Yl is CH, Y2 is CH, Y3 is CH, X5 is CN, R5 and R2 have the values listed in the Table X.
  • Table 7X provides 18 compounds of Formula X5-A wherein Gl is oxygen, Rl is hydrogen, Yl is CH, Y2 is CH, Y3 is CH, X5 is OH, R5 and R2 have the values listed in the Table X.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
  • insects from the family of Curculionidae. are Anthonomus corvulus,
  • the invention provides a compound selected from Tables IP to 16P for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus Diabrotica.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Diabrotica virgifera.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Diabrotica barberi.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Diabrotica undecimpunctata howardi.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing wireworms, in particular Agriotes spp.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
  • Agriotes spp. include Agriotes Uneatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing grubs, in particular white grubs. In one embodiment the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Phyllophaga spp., particularly on corn, soybean or cotton.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
  • white grubs include Phyllophaga anxia, Phyllophaga crinite, Phyllophaga subnitida, Diloboderus abderus.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing termites, e.g. on sugarcane.
  • termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes, Globitermes.
  • specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp..
  • Specific examples of dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp..
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing cutworms, e.g. agrotis spp..
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing millipedes, e.g. Julus spp..
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing whitefly.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes. In one embodiment the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Trialeurodes vapor ariorum, particularly on vegetables, cotton, soybean, or potatoes.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing stinkbugs, in particular Euschistus spp.
  • the invention provides a compound selected from Tables IP to 16P for use in controlling and/or preventing Euschistus spp., particularly in soybean.
  • stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinii), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g.
  • Eurygaster intergriceps, Eurygaster maura Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
  • Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinii, Halyomorpha halys.
  • the stinkbug target is Nezara viridula, Piezodorus spp., Acrosternum spp, Euchistus heros.
  • the invention provides a compound selected from Tables IP to 16P for use against rice pests.
  • the invention provides a compound selected from Tables IP to 16P for use against stemborer, particularly in rice.
  • Sesamia sp Sesamia inferens.
  • the invention provides a compound selected from Tables IP to 16P for use against leaffolder, particularly in rice.
  • leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua.
  • the invention provides a compound selected from Tables IP to 16P for use against hoppers, particularly in rice.
  • Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
  • the invention provides a compound selected from Tables IP to 16P for use against gallmidge, particularly in rice.
  • Gall midge examples include Orseolia sp, Orseolia oryzae.
  • the invention provides a compound selected from Tables IP to 16P for use against whorl maggot, particularly in rice.
  • whorl maggots include Hydrellia sp, Hydrellia philippina.
  • the invention provides a compound selected from Tables IP to 16P for use against Rice bugs, particularly in rice.
  • rice bugs examples include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.
  • the invention provides a compound selected from Tables IP to 16P for use against Black bugs, particularly in rice.
  • Black bugs examples include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.
  • the invention provides a compound selected from Tables IP to 16P for use against plutella spp..
  • the invention provides a compound selected from Tables IP to 16P for use against Plutella xylostella, particularly in brassica crops.
  • the invention provides a method of controlling insects, acarines, nematodes or molluscs, preferably in a crop of useful plants, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula ⁇
  • G 1 is oxygen
  • R 1 is hydrogen
  • R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, l,l -dioxo-thietan-3-yl-, thietan-3-ylmethyl-, l-oxo-thietan-3- ylmethyl-, or l,l -dioxo-thietan-3-ylmethyl-;
  • Y 1 , Y 2 and Y 3 are independently CH or nitrogen;
  • R 5 is hydrogen, halogen, cyano, nitro, NH 2 , Ci-C 2 alkyl, Ci-C 2 haloalkyl, C3-C 5 cycloalkyl, d- C 2 halocycloalkyl, Ci-C 2 alkoxy, Ci-C 2 haloalkoxy;
  • X 2 is C-X 6 ;
  • ⁇ ', ⁇ 3 and X 6 are independently halogen or trihalomethyl
  • X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl.
  • X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro, or X is chloro, X is C-Br, X is chloro, or
  • X 1 is chloro, X2 is C-Cl, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, or X 1 is fluoro, X 2 is C-F, X 3 is fluoro, and X 4 is CF 3 , then the method does not comprise applying the compound of formula I to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs; and/or
  • the compound is not a compound wherein R 2 is thietan-3-yl-, l -oxo-thietan-3-yl-, 1,1 - Dioxo-thietan-3-yl-; Y 1 , Y 2 and Y 3 are CH; R 5 is methyl; X 2 is bromo, X 2 is C-Cl, X 3 is bromo and X 4 is CF 3 .
  • the invention provides a method of protecting useful plants from insects, acarines, nematodes or molluscs, comprising applying to said plant, to the locus thereof, or to plant propagation material thereof, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula ⁇ as defined above, including preferences thereof.
  • said methods do not comprise applying the compound of formula ⁇ to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
  • R 2 is thietan-3-yl-, l-oxo-thietan-3-yl-, or l,l -dioxo-thietan-3-yl-.
  • R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, even more preferably R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl. Most preferably R 5 is chloro or methyl.
  • Y 1 is CH, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is CH, Y 3 is N. More preferably Y 1 is CH, Y 2 is CH, Y 3 is CH.
  • X is chloro
  • X is C-Br
  • X is chloro
  • X is chloro
  • X is C-F
  • X is chloro
  • X 2 is C-Cl
  • X 3 is chloro
  • X 1 is chloro
  • X 2 is C-I
  • X 3 is chloro
  • X 1 is fluoro
  • X 2 is C-F
  • X 3 is
  • X is chloro, X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro.
  • X 4 is trifluoromethyl.
  • the invention provides compounds of formula ⁇ wherein
  • G 1 is oxygen
  • R 1 is hydrogen
  • R 2 is thietan-3-yl-, l -oxo-thietan-3-yl-, l,l -Dioxo-thietan-3-yl-, thietan-3-ylmethyl-, 1 -oxo- thietan-3-ylmethyl-, or l,l -Dioxo-thietan-3-ylmethyl-;
  • Y 1 is CH, Y 2 is CH, Y 3 is CH; R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl;
  • X is chloro, X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro;
  • X 4 is trifluoromethyl.
  • G 1 is oxygen
  • R 1 is hydrogen
  • R is thietan-3-yl-, l -oxo-thietan-3-yl-, l,l -Dioxo-thietan-3-yl-;
  • Y 1 is CH, Y 2 is CH, Y 3 is CH;
  • R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl
  • X is chloro, X is C-Cl, X is chloro, or X is chloro, X is C-F, X is chloro;
  • X is trifluoromethyl
  • the invention provides compounds of formula ⁇ wherein X 1 is chloro, X 2 is C-Br,
  • X J is chloro and G , R , R R D , Y , Y Y J and X" are as defined for the compound of formula ⁇ .
  • the invention provides compounds of formula ⁇ wherein X 1 is chloro, X 2 is C-F,
  • X J is chloro and G , R , R R D , Y , Y Y J and X" are as defined for the compound of formula ⁇ .
  • the invention provides compounds of formula ⁇ wherein X 1 is chloro, X 2 is C-Cl,
  • X J is chloro and G , R , R R Y , Y Y J and X" are as defined for the compound of formula ⁇ .
  • the invention provides compounds of formula ⁇ wherein X 1 is chloro, X 2 is C-I,
  • X J is chloro and G , R , R R Y , Y Y J and X" are as defined for the compound of formula ⁇ .
  • the invention provides compounds of formula ⁇ wherein X 1 is fluoro, X 2 is C-F,
  • X J is fluoro and G , R , R R Y , Y Y J and X" are as defined for the compound of formula ⁇ .
  • the invention provides compounds of formula ⁇ wherein X 1 is chloro, X 2 is C-Cl,
  • X J is trifluoromethyl and G , R , R R Y , Y Y J and X" are as defined for the compound of formula ⁇ .
  • the invention provides compounds of formula ⁇ wherein X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl and G 1 , R 1 , R 2 , R 5 , Y 1 , Y 2 , Y 3 and X 4 are as defined for the compound of formula ⁇ .
  • Table Q indicates compounds of formula Faccording to the above aspect of the invention.
  • Table 1Q provides 72 compounds of Formula ⁇ - ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.
  • Table 2Q provides 72 compounds of Formula ⁇ - ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.
  • Table 3Q provides 72 compounds of Formula ⁇ - ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.
  • Table 4Q provides 72 compounds of Formula ⁇ - ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.
  • Table 5Q provides 72 compounds of Formula ⁇ - ⁇ wherein Gl is oxygen, Rl is hydrogen, Xlis fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.
  • Table 6Q provides 72 compounds of Formula ⁇ - ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.
  • Table 7Q provides 72 compounds of Formula ⁇ - ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-CL, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table Q.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
  • insects from the family of Curculionidae. are Anthonomus corvulus,
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing soil pests.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus Diabrotica.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Diabrotica virgifera.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Diabrotica barberi.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Diabrotica undecimpunctata howardi.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing wireworms, in particular Agriotes spp.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
  • Agriotes spp. include Agriotes lineatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Phyllophaga spp., particularly on corn, soybean or cotton.
  • the invention provides a compound selected from Tables 1Q to 7Q for use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton. In one embodiment the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
  • white grubs include Phyllophaga anxia, Phyllophaga crinite,
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing termites, e.g. on sugarcane.
  • termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes,
  • Globitermes Specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp.. Specific examples of dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes spp. and procornitermes araujoi
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp..
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing cutworms, e.g. agrotis spp..
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing millipedes, e.g. Julus spp..
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane.
  • the invention provides a compound selected from Tables 1Q to 7Q for use in controlling and/or preventing whitefly.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Trialeurodes vaporariorum, particularly on vegetables, cotton, soybean, or potatoes.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing stinkbugs, in particular Euschis tus spp. In one embodiment the invention provides a compound selected from Tables 1 Q to 7Q for use in controlling and/or preventing Euschistus spp., particularly in soybean.
  • stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinii), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g.
  • Eurygaster intergriceps, Eurygaster maura Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
  • Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinii, Halyomorpha halys.
  • the stinkbug target is Nezara viridula, Piezodorus spp., Acrosternum spp, Euchistus heros.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against rice pests.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against stemborer, particularly in rice.
  • Sesamia sp Sesamia inferens.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against leaffolder, particularly in rice.
  • leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against hoppers, particularly in rice.
  • Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against gallmidge, particularly in rice.
  • Gall midge examples include Orseolia sp, Orseolia oryzae.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against whorl maggot, particularly in rice.
  • whorl maggots include Hydrellia sp, Hydrellia philippina.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against Rice bugs, particularly in rice.
  • rice bugs examples include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against Black bugs, particularly in rice.
  • Black bugs examples include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against plutella spp..
  • the invention provides a compound selected from Tables 1 Q to 7Q for use against Plutella xylostella, particularly in brassica crops.
  • the invention provides a method of controlling insects, acarines, nematodes or molluscs, preferably in a crop of useful plants, which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I")
  • G 1 is oxygen
  • R 1 is hydrogen
  • R 2 is thietan-3-ylmethyl-, l -oxo-thietan-3-ylmethyl-, l , l -dioxo-thietan-3-ylmethyl-;
  • Y 1 , Y 2 and Y 3 are independently CH or nitrogen;
  • R 5 is hydrogen, halogen, cyano, nitro, NH 2 , Ci-C 2 alkyl, Ci-C 2 haloalkyl, C 3 -C 5 cycloalkyl, C r
  • X 2 is C-X 6 or nitrogen
  • ⁇ ', ⁇ 3 and X 6 are independently hydrogen, halogen or trihalomethyl, wherein at least two of X 1 , X 3 and X 6 are not hydrogen;
  • X 4 is trifluoromethyl, difluoromethyl or chlorodifluoromethyl
  • X is CH, X is chloro, or X is chloro, X is C-F, X is hydrogen, or X is fluoro, X is C-Cl, X is hydrogen,
  • X is chloro, X is C-Cl, X is hydrogen, or X is chloro, X is CH, X is bromo, or X is chloro, X is CH, X 3 is fluoro, or X 1 is chloro, X 2 is CH, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is C-H, X 3
  • 1 2 3 1 2 3 is trifluoromethyl, or X is trifluoromethyl, X is CH, X is hydrogen, or X is chloro, X is C-Cl, X is 1 2 3 1 2 3 1 2 chloro, or X is chloro, X is C-F, X is chloro, or X is chloro, X is C-Br, X is chloro, or X is fluoro, X is C-F, X 3 is fluoro; or X 1 is chloro, X2 is C-Cl, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, and X 4 is CF 3 , then the method does not comprise applying the compound of formula I to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
  • the method does not comprise applying the compound of formula I" to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
  • the invention provides a method of protecting useful plants from insects, acarines, nematodes or molluscs, comprising applying to said plant, to the locus thereof, or to plant propagation material thereof, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula ⁇ ' as defined above, including preferences thereof.
  • said methods do not comprise applying the compound of formula ⁇ ' to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
  • R 2 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 , X 4 , X 5 and X 6 for compounds of formula I" are, in any combination, as set out below.
  • R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, more preferably R 5 is hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, nitro, cyano, cyclopropyl, even more preferably R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl. Most preferably R 5 is chloro or methyl.
  • Y 1 is CH, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is CH, Y 3 is CH, or Y 1 is N, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is N, Y 3 is CH, orY 1 is CH, Y 2 is CH, Y 3 is N. More preferably Y 1 is CH, Y 2 is CH, Y 3 is CH.
  • X is chloro
  • X is CH
  • X is chloro
  • X is chloro
  • X is C-F
  • X is hydrogen
  • X is hydrogen
  • X is C-I, X is chloro, or X is fluoro, X is C-F, X is fluoro, orX is chloro, X is CH, X is
  • X is chloro
  • X is CH, X is fluoro, orX is chloro
  • X is CH, X is trifluoromethyl, or X is chloro
  • X 2 is C-Cl
  • X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is C-Cl, X 3 is trifluoromethyl, or X 1 is trifluoromethyl, X 2 is CH, X 3 is hydrogen, or
  • X 1 is chloro, X 2 is N, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is N, X 3 is trifluoromethyl.
  • X 1 is chloro, X 2 is CH, X 3 is chloro, or X 1 is chloro, X 2 is C-Cl, X 3 is chloro, or X 1 is chloro, X 2 is C-F, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl.
  • X 1 is chloro, X 2 is CH, X 3 is chloro.
  • X 4 is trifluoromethyl.
  • the invention provides compounds of formula I" wherein G 1 is oxygen;
  • R 1 is hydrogen
  • R 2 is thietan-3 -ylmethyl-, 1 -oxo-thietan-3 -ylmethyl-, or 1,1 -Dioxo-thietan-3 -ylmethyl-;
  • Y 1 is CH, Y 2 is CH, Y 3 is CH;
  • R 5 is chloro, bromo, fluoro, methyl, trifluoromethyl
  • X 1 is chloro, X 2 is CH, X 3 is chloro, X 1 is chloro, X 2 is C-Cl, X 3 is chloro, X 1 is chloro, X 2 is C-F, X 3 is chloro, or X 1 is trifluoromethyl, X 2 is CH, X 3 is trifluoromethyl;
  • X 4 is trifluoromethyl.
  • the invention provides compounds of formula I" wherein R 2 is thietan-3 - ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I".
  • the invention provides compounds of formula I" wherein R 2 is 1 -oxo-thietan-3 - ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I".
  • the invention provides compounds of formula I" wherein R 2 is 1,1-Dioxo-thietan- 3-ylmethyl- and G 1 , R 1 , R 5 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , X 3 and X 4 are as defined for the compound of formula I".
  • Table S indicates compounds according to the above aspect of the invention.
  • Table I S provides 36 compounds of Formula I"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 2S provides 36 compounds of Formula ⁇ '- ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 3S provides 36 compounds of Formula ⁇ '- ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is fluoro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 4S provides 36 compounds of Formula I"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 5S provides 36 compounds of Formula ⁇ '- ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-F, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 6S provides 36 compounds of Formula I"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 7S provides 36 compounds of Formula I"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Br, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 8S provides 36 compounds of Formula I"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-I, X3 is chloro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 9S provides 36 compounds of Formula ⁇ '- ⁇ wherein Gl is oxygen, Rl is hydrogen, Xlis fluoro, X2 is C-F, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 10S provides 36 compounds of Formula ⁇ '- ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X2 is bromo, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 1 I S provides 36 compounds of Formula I"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is fluoro, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 12S provides 36 compounds of Formula ⁇ '- ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 13S provides 36 compounds of Formula I"-A wherein Gl is oxygen, Rl is hydrogen, XI is chloro, X2 is C-Cl, X3 is trifluoromehtyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 14S provides 36 compounds of Formula ⁇ '- ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 15S provides 36 compounds of Formula ⁇ '- ⁇ wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is C-Cl, X3 is trifluoromethyl, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • Table 16S provides 36 compounds of Formula I"-A wherein Gl is oxygen, Rl is hydrogen, XI is trifluoromethyl, X2 is CH, X3 is hydrogen, Yl is CH, Y2 is CH, Y3 is CH and X4, R5 and R2 have the values listed in the Table S.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
  • insects from the family of Curculionidae. are Anthonomus corvulus,
  • the invention provides a compound selected from Tables 1 S to 16S for use against Anthonomus grandis in cotton.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing soil pests. In one embodiment the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus Diabrotica.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Diabrotica virgifera.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Diabrotica barberi.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Diabrotica undecimpunctata howardi.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing wireworms, in particular Agriotes spp.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
  • Agriotes spp. include Agriotes Uneatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Phyllophaga spp., particularly on corn, soybean or cotton.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
  • white grubs include Phyllophaga anxia, Phyllophaga crinite,
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing termites, e.g. on sugarcane.
  • termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes, Globitermes.
  • Specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp..
  • dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes spp. and procornitermes araujoi In one embodiment the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp..
  • the invention provides a compound selected from Tables I S to 16S for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing cutworms, e.g. agrotis spp..
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing millipedes, e.g. Julus spp..
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing whitefly.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Trialeurodes vapor ariorum, particularly on vegetables, cotton, soybean, or potatoes.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing stinkbugs, in particular Euschistus spp.
  • the invention provides a compound selected from Tables 1 S to 16S for use in controlling and/or preventing Euschistus spp., particularly in soybean.
  • stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinii), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g.
  • Eurygaster intergriceps, Eurygaster maura Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
  • Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinii, Halyomorpha halys.
  • the stinkbug target is Nezara viridula, Piezodorus spp., Acrosternum spp, Euchistus heros.
  • the invention provides a compound selected from Tables 1 S to 16S for use against rice pests. In one embodiment the invention provides a compound selected from Tables 1 S to 16S for use against stemborer, particularly in rice.
  • Sesamia sp Sesamia inferens.
  • the invention provides a compound selected from Tables 1 S to 16S for use against leaffolder, particularly in rice.
  • leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua.
  • the invention provides a compound selected from Tables 1 S to 16S for use against hoppers, particularly in rice.
  • Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
  • the invention provides a compound selected from Tables 1 S to 16S for use against gallmidge, particularly in rice.
  • Gall midge examples include Orseolia sp, Orseolia oryzae.
  • the invention provides a compound selected from Tables 1 S to 16S for use against whorl maggot, particularly in rice.
  • whorl maggots include Hydrellia sp, Hydrellia philippina.
  • the invention provides a compound selected from Tables 1 S to 16S for use against Rice bugs, particularly in rice.
  • rice bugs examples include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.
  • the invention provides a compound selected from Tables 1 S to 16S for use against Black bugs, particularly in rice.
  • Black bugs examples include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.
  • the invention provides a compound selected from Tables 1 S to 16S for use against plutella spp..
  • the invention provides a compound selected from Tables 1 S to 16S for use against Plutella xylostella, particularly in brassica crops.
  • Compounds of formula I include at least one chiral centre and may exist as compounds of formula I* or compounds of formula I**.
  • Compounds I* and I** are enantiomers if there is no other chiral center or epimers otherwise.
  • mixtures of compounds I* and I** in any ratio e.g. in a molar ratio of 1 :99 to 99: 1, e.g. 10: 1 to 1 : 10, e.g. a substantially 50:50 molar ratio.
  • the molar proportion of compound I** compared to the total amount of both enantiomers is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.
  • the molar proportion of the compound of formula I* compared to the total amount of both enantiomers (or epimerically) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%.
  • Enantiomerically (or epimerically) enriched mixtures of formula I** are preferred. Where compounds of formula I contain an SO group, cis SO groups are preferred. When compounds of formula I** contain an SO group, cis SO groups are preferred.
  • Each of the compounds disclosed in Tables IP to 270P represents a specific disclosure of a compound with the R configuration (i.e. at the corresponding position indicated for compounds I* and I**) and a specific disclosure of a compound having the S configuration (i.e. at the corresponding position indicated for compounds I* and I**).
  • Each compound disclosed in Tables IP to 16P, 1Q to 7Q and I S to 7S represents a specific disclosure of a compound according to the compound of formula I* and a specific disclosure of a compound according to the compound of formula II*.
  • the invention provides a method of controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of
  • a 1 , A 2 , A 3 and A 4 are independently of one another C-H, C-R 3 , or nitrogen;
  • B is O or CH 2 ;
  • R 1 is Ci-Cghaloalkyl
  • R 2 is aryl or aryl substituted by one to five R 4 , or heteroaryl or heteroaryl substituted by one to five R 4 ; each R 3 is independently halogen, cyano, nitro, Q-Qalkyl, C 3 -C 8 cycloalkyl, Ci-Cghaloalkyl, C 2 - Qalkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, C r C 8 alkoxycarbonyl-, amino, hydroxy, mercapto, Ci-C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, Ci-C 8 haloalky
  • each R 4 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 - C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, hydroxy, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, mercapto, Cp C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, Ci-C 8 alkylsulfonyl, Cp Cghaloalkylsulfonyl, Q-Qalkylcarbonyl, CpQalkoxycarbonyl, aryl or aryl substituted by one to five R 5 , or heterocyclyl or heterocyclyl substituted by one to five R 5
  • each R 5 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 alkoxy-, or Q- C 4 haloalkoxy-.
  • the invention provides a method of protecting useful plants from insects, acarines, nematodes or molluscs, comprises applying a plant, to the locus thereof, or to plant propagation material thereof, an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula IA.
  • said methods do not comprise applying the compound of formula IA to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
  • the invention provides a method of controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a ffective amount of a compound of
  • a 1 , A 2 , A 3 and A 4 are independently of one another C-H, C-R 3 , or nitrogen;
  • B is O or CH 2 ;
  • R 1 is Ci-Cghaloalkyl
  • R 2 is aryl or aryl substituted by one to five R 4 , or heteroaryl or heteroaryl substituted by one to five R 4 ; each R 3 is independently halogen, cyano, nitro, CpCgalkyl, C3-Cgcycloalkyl, Ci-Cghaloalkyl, C 2 - Cgalkenyl, C 2 -Cghaloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, Q-Qalkoxy, Q-Qhaloalkoxy, C r Cgalkoxycarbonyl-, amino, hydroxy, mercapto, CpCgalkylthio, Ci-Cghaloalkylthio, Ci-Cgalkylsulfinyl, Ci-Cghaloalkylsulfinyl, Q-Cgalkylsulfonyl, CpCghaloalkylsulfonyl, CpCgalky
  • each R 4 is independently halogen, cyano, nitro, Q-Cgalkyl, Ci-Cghaloalkyl, C 2 -C 8 alkenyl, C 2 - Cghaloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, hydroxy, Ci-C 8 alkoxy, Ci-C 8 haloalkoxy, mercapto, C r C 8 alkylthio, Ci-C 8 haloalkylthio, Ci-C 8 alkylsulfinyl, Ci-C 8 haloalkylsulfinyl, CpQalkylsulfonyl, C r C 8 haloalkylsulfonyl, Ci-C 8 alkylcarbonyl, Ci-C 8 alkoxycarbonyl, aryl or aryl substituted by one to five R 5 , or heterocyclyl or heterocyclyl substituted by one to five R 5
  • each R 5 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy-, or Q-
  • n 0,1 or 2.
  • said methods do not comprise applying the compound of formula IB to a crop of soybean plants, the locus thereof, or propagation material thereof, and the method is not for control of stinkbugs.
  • a 1 is C-H or C-R 3 and no more than two of A 2 , A 3 and A 4 are nitrogen, more preferably no more than two of A 2 , A 3 and A 4 are nitrogen and A 3 and A 4 are not both nitrogen.
  • a 1 is C-H or C-R 3
  • a 2 is C-H, C-R 3 or nitrogn
  • a 1 is C-H or C-R 3 , most preferably A 1 is C-R 3 .
  • a 2 is C-H or C-R 3 , most preferably A 2 is C-H.
  • a 3 is C-H or C-R 3 , most preferably A 3 is C-H.
  • a 4 is C-H or C-R 3 , most preferably A 4 is C-H.
  • R 1 is chlorodifluoromethyl, difluoromethyl or trifluoromethyl, more preferably chlorodifluoromethyl or trifluoromethyl, most preferably trifluoromethyl.
  • R 2 is aryl or aryl substituted by one to three R 4 , more preferably R 2 is phenyl or phenyl substituted by one to three R 4 , pyridyl or pyridyl substituted by one to three R 4 , more preferably R 2 is phenyl substituted by one to three R 4 or pyridyl substitued by one to three R 4 , more preferably R 2 is group P
  • R 2 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3- bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3- trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3-bromo-5-chlorophenyl, 4-fluoro-3,5- dichlorophenyl or 3,4,5-trichloro-phenyl, 3-chloro-4-fluorophenyl, 3-fluoro-4-chlorophenyl, 4-bromo-3,5- dichlorophenyl, 4-iodo-3,5-dichlorophenyl, 3,4,5-trifluorophenyl, 3 -chloro-5
  • each R 4 is independently halogen, cyano, nitro, CpCgalkyl, Q-Cghaloalkyl, C r Cgalkoxy, Ci-Cghaloalkoxy, more preferably iodo, bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, most preferably bromo, chloro, fluoro, iodo or trifluoromethyl.
  • the invention provides a compound of formula IA or IB for use in controlling and/or preventing insects of the family Curculionidae, preferably in for use in controlling and/or preventing Anthonomus grandis.
  • insects from the family of Curculionidae. are Anthonomus corvulus,
  • the invention provides a compound compound of formula IA or IB for use against Anthonomus grandis in cotton.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing soil pests.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing corn rootworm, in particular for use against corn root worm from the genus Diabrotica. In one embodiment the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Diabrotica virgifera.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Diabrotica barberi.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Diabrotica undecimpunctata howardi.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing wireworms, in particular Agriotes spp.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Agriotes spp. in cereals, potato or corn.
  • Agriotes spp. include Agriotes Uneatus, Agriotes obscurus, Agriotes brevis, Agriotes gurgistanus, Agriotes sputator, Agriotes ustulatus, Ctenicera destructor, and Limonius californicus.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing grubs, in particular white grubs.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Phyllophaga spp., particularly on corn, soybean or cotton.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Diloboderus spp. particularly on corn, soybean or cotton.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Popillia japonica, particularly on corn, soybean or cotton.
  • white grubs include Phyllophaga anxia, Phyllophaga crinite, Phyllophaga subnitida, Diloboderus abderus.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing termites, e.g. on sugarcane.
  • termites include Reticulitermes, Coptotermes, Macrotermes, Microtermes, Globitermes.
  • specific of subterranean termites include Reticulitermes flavipes, Reticulitermes hesperus, Reticulitermes verginicus, Reticulitermes hageni, Reticulitermes speratus, Reticulitermes lucifugus, Heterotermes aureus, Coptotermes formosanus, Coptotermes acinaciformis, Coptotermes curvignathus, Nasutitermes exitiosus, Nasutitermes walkeri, Mastotermes darwiniensis, Schedorhinotermes spp, Macrotermes bellicosus, Macrotermes spp., Globitermes sulphureus, Odontotermes spp..
  • Specific examples of dry wood termites include Incisitermes minor, Marginitermes hubbardi, Cryptotermes brevis, Kalotermes flavicollis. Additional examples of termites include procornitermes
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing subterraneous stinkbugs, e.g. Scaptocoris spp..
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Scaptocoris castaneus, in particular on cereals, soybean or corn. In one embodiment the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing cutworms, e.g. agrotis spp..
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Agrotis ipsilon, particularly on cereals, canola, soybean or corn.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing millipedes, e.g. Julus spp..
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Julus spp., particularly on cereals, canola, soybean & corn.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing broca gigante, e.g. Telchin licus, particularly on sugarcane.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing whitefly.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Bemisia tabaci, particularly on vegetables, cotton, soybean, or potatoes.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Trialeurodes vapor ariorum, particularly on vegetables, cotton, soybean, or potatoes.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing stinkbugs, in particular Euschistus spp.
  • the invention provides a compound compound of formula IA or IB for use in controlling and/or preventing Euschistus spp., particularly in soybean.
  • stinkbugs include Nezara spp. (e.g. Nezara viridula, Nezara antennata, Nezara hilare), Piezodorus spp. (e.g. Piezodorus guildinii), Acrosternum spp. Euchistus spp. (e.g. Euchistus heros, Euschistus servus), Halyomorpha halys, Plautia crossota, Riptortus clavatus, Rhopalus msculatus, Antestiopsis orbitalus, Dichelops spp. (e.g. Dichelops furcatus, Dichelops melacanthus), Eurygaster spp. (e.g.
  • Eurygaster intergriceps, Eurygaster maura Oebalus spp. (e.g. Oebalus mexicana, Oebalus poecilus, Oebalus pugnase, Scotinophara spp. (e.g. Scotinophara lurida, Scotinophara coarctata).
  • Preferred targets include Antestiopsis orbitalus, Dichelops furcatus, Dichelops melacanthus, Euchistus heros, Euschistus servus, Nezara viridula, Nezara hilare, Piezodorus guildinii, Halyomorpha halys.
  • the stinkbug target is Nezara viridula, Piezodorus spp., Acrosternum spp, Euchistus heros.
  • the invention provides a compound compound of formula IA or IB for use against rice pests.
  • the invention provides a compound compound of formula IA or IB for use against stemborer, particularly in rice.
  • Sesamia sp Sesamia inferens.
  • the invention provides a compound compound of formula IA or IB for use against leaffolder, particularly in rice.
  • leaffolders include Cnaphalocrocis spp., Cnaphalocrocis medinalis, Marasmia spp., Marasmia patnalis, Marasmia exigua.
  • the invention provides a compound compound of formula IA or IB for use against hoppers, particularly in rice.
  • Hoppers include Nephotettix spp., Nephotettix virescens, Nephotettix nigropictus, Nephotettix malayanus, Nephotettix cincticeps, Nilaparvata lugens, Sogatella furcifera.
  • the invention provides a compound compound of formula IA or IB for use against gallmidge, particularly in rice.
  • Gall midge examples include Orseolia sp, Orseolia oryzae.
  • the invention provides a compound compound of formula IA or IB for use against whorl maggot, particularly in rice.
  • whorl maggots include Hydrellia sp, Hydrellia philippina.
  • the invention provides a compound compound of formula IA or IB for use against Rice bugs, particularly in rice.
  • rice bugs examples include Leptocorisa sp, Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta.
  • the invention provides a compound compound of formula IA or IB for use against Black bugs, particularly in rice.
  • Black bugs examples include Scotinophara sp, Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula.
  • the invention provides a compound compound of formula IA or IB for use against plutella spp..
  • the invention provides a compound compound of formula IA or IB for use against Plutella xylostella, particularly in brassica crops.
  • Compounds of formula (I) can be prepared by reacting a compound of formula (V) wherein R is OH, Ci-C 6 alkoxy or CI, F or Br, with an amine of formula (XX), wherein L is methylene or ethylene, as shown in Scheme 1.
  • R When R is OH such reactions are usually carried out in the presence of a coupling reagent, such as ⁇ , ⁇ '-dicyclohexylcarbodiimide (“DCC”), l-ethyl-3-(3-dimethylamino-propyl)- carbodiimide hydrochloride (“EDC”) or bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP-Cl”), in the presence of a base, and optionally in the presence of a nucleophilic catalyst, such as hydroxybenzotriazole (“HOBT").
  • DCC ⁇ , ⁇ '-dicyclohexylcarbodiimide
  • EDC l-ethyl-3-(3-dimethylamino-propyl)- carbodiimide hydrochloride
  • BOP-Cl bis(2-oxo-3-oxazolidinyl)phosphonic chloride
  • R When R is CI, such reactions are usually carried out in
  • Suitable bases include pyridine, triethylamine, 4-(dimethylamino)-pyridine ("DMAP”) or diisopropylethylamine (Hunig's base).
  • Preferred solvents are NN-dimethylacetamide, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane, ethyl acetate and toluene.
  • the reaction is carried out at a temperature of from 0°C to 100°C, preferably from 15°C to 30°C, in particular at ambient temperature.
  • Amines of formula (XX) are either known in the literature or can be prepared using methods known to a person skilled in the art. Some of these methods are described in the preparation examples.
  • Acid halides of formula (V), wherein R is CI, F or Br may be made from carboxylic acids of formula (V), wherein R is OH, under standard conditions, as described for example in WO2008/128711.
  • Carboxylic acids of formula (V), wherein R is OH may be formed from esters of formula (V), wherein R is Ci-C 6 alkoxy as described for example in WO2009/072621.
  • Compounds of formula (I) can be prepared by reacting a compound of formula (VI) wherein X B is a leaving group, for example a halogen, such as bromo, with carbon monoxide and an amine of formula (X), in the presence of a catalyst, such as palladium(II) acetate or bis-
  • triphenylphosphine and a base, such as sodium carbonate, pyridine, triethylamine, 4-(dimethylamino)- pyridine ("DMAP") or diisopropylethylamine (Hunig's base), in a solvent, such as water, NN- dimethylformamide or tetrahydrofuran.
  • a base such as sodium carbonate, pyridine, triethylamine, 4-(dimethylamino)- pyridine (“DMAP”) or diisopropylethylamine (Hunig's base)
  • DMAP dimethylamino)- pyridine
  • Hunig's base diisopropylethylamine
  • -OP(0)(OR x ) 2 wherein R x is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, preferably halogen, more preferably bromo, can be made by a various of methods, for example as described in WO2009/080250.
  • Scheme 2
  • Thietan-3-nitrile (III) can be obtained by reaction of epithiochlorhydrin (II) with a cyanide M- CN, such as sodium cyanide or potassium cyanide in the presence of water, preferably as a co-solvent with an organic solvent such as benzene or tetrahydrofuran, at a temperature of 20°C to 100°C, preferably 40-60°C preferably around 50°C.
  • a cyanide M- CN such as sodium cyanide or potassium cyanide
  • an organic solvent such as benzene or tetrahydrofuran
  • Water is preferably used as a solvent, more preferably as a co-solvent with an organic solvent, preferably a water-immiscible organic solvent, e.g. such that the reaction then takes place in a biphasic system.
  • the organic co-solvent is preferred to be aprotic, and is more preferably chosen from pentane, hexane, heptane, cyclohexane, benzene, toluene, xylene, tetrahydrofuran, ethyl acetate, diethyl ether, or methyl- tert-butyl ether.
  • the reaction can be performed with an excess of epithiochlorhydrin or with an excess of M-CN, preferably in stoechiometric ratio or slight excess of one or the other reagent.
  • Compounds of formula (IV) can be prepared by reaction of compounds of formula (III) with a suitable reducing reagent.
  • a suitable reducing reagent is the use of metal hydride reagents, such as lithium aluminum hydride or borane, in the presence or not of cocatalysts. Other methods that can be carried out involve the hydrogenation in the presence of Raney Ni, or palladium for instance.
  • the most common solvents for this reaction are alcohols such as methanol or ethanol, tetrahydrofuran, toluene, ethers, such as diethyl ether or methyl tert-butyl ether.
  • reaction time in most cases is between 30 minutes and 12 hours.
  • Compounds of formula (IX) can be prepared by reaction of compounds of formula (VIII) with a suitable reducing reagent.
  • a suitable reducing reagent is the use of metal hydride reagents, such as sodium borohydride.
  • metal hydride reagents such as sodium borohydride.
  • Other methods that can be carried out involve the hydrogenation under a hydrogen atmosphere in the presence of palladium for instance.
  • the most common solvents for this reaction are alcohols such as methanol or ethanol. In most cases it is advantageous to conduct the reaction at dilution between 0.1 M to 1 M, preferably 0.3 M to 0.5 M, at a temperature of 0°C to 100°C, preferably 0-80°C preferably around 20°C, and the reaction time in most cases is between 30 minutes and 12 hours.
  • Compounds of formula (X) can be prepared by reaction of compounds of formula (IX) with a suitable reducing reagent.
  • a suitable reducing reagent is the use of metal hydride reagents, such as lithium aluminum hydride or borane, in the presence or not of cocatalysts. Other methods that can be carried out involve the hydrogenation in the presence of Raney Ni, or palladium for instance.
  • the most common solvents for this reaction are alcohols such as methanol or ethanol, tetrahydrofuran, toluene, ethers, such as diethyl ether or methyl tert-butyl ether.
  • reaction time in most cases is between 30 minutes and 12 hours.
  • compounds of formula (X) may be obtained directly by reduction of compounds of formula (VIII), for example under hydrogenation conditions, e.g. using hydrogen and a metal hydrogenation catalyst, e.g. Palladium, Rhodium, or Plattinum.
  • a metal hydrogenation catalyst e.g. Palladium, Rhodium, or Plattinum.
  • Compound (IV) may be prepared by reduction of a nitromethylene compound of formula (XI).
  • Reducing agents suitable for this reduction include for example metal hydride reagents such as sodium borohydride or lithium aluminium hydride optionally in the presence of a catalyst, for example nichel chloride. Hydrogenation in the presence of metal catalyst such as raney nickel or palladium on charcoal is an alternative for such reductions. Examples of such methods can be found in Journal of the American Chemical Society (2003), 125(40), 12125-12136, US patent n° 20050261327, or in Journal of Medicinal Chemistry (2010), 53(7), 2942-2951.
  • the amine of formula (IV) may be obtained from the carboxylic acid of formula (XIII) using Schmidt or Curtius rearrangement.
  • Schmidt rearrangement involves treatment with hydrazoic acid under a range of possible conditions known to the person skilled of the art, for example as described in Journal of Organic Chemistry, 58(6), 1372-6; 1993 for the conversion of bicyclo[ 1.1.1 ]pentane-2- carboxylic acid to bicyclo[l . l. l]pentane-2-amine.
  • Curtius rearrangement can be carried out under different possible conditions known to the person skilled in the art, for example treatment of (XIII) with diphenylphosphoryl azide followed by heating and reaction with an alcohol such as benzyl alcohol or tert- butanol; the corresponding ester is obtained and subsequently deprotected to the amine by hydrogenolysis (benzyl ester) or treatment with trifluoroacetic acid (tert-butyl ester).
  • an alcohol such as benzyl alcohol or tert- butanol
  • benzyl ester tert-butanol
  • Such conditions are for example described in Journal of Organic Chemistry, 75(17), 5941 -5952, 2010 or Tetrahedron: Asymmetry, 14(23), 3773-3778; 2003.
  • the acid of formula (XII) may derive from the ketone of formula (VII) after homologation of the ketone (VII) to an ester of formula (XII) followed by hydride reduction or hydrogenation of the double bond.
  • Similar synthetic sequences from related substrates are described for example in Chemical & Pharmaceutical Bulletin, 52(6), 675-687; 2004, Synlett (2005), (10), 1559-1562, WO 2005019221, or WO 2010031735.
  • Amines of formula (IV) and (X) may be converted to further amine intermediates of formula (XIV) and (XV) wherein n is 1 or 2.
  • the amines may be directly oxidized or first protected, oxidized and then deprotected.
  • the amine of formula (XVII) may be obtained from a compound of formula (XVI) wherein each X B is independently hydroxy, halogen or a leaving group such as mesylate, tosylate or triflate.
  • the sequence is then similar to that described for example in WO 2007080131 for the conversion of serinol to thietan-3ylamine.
  • Compounds of formula (XVI) are either known compounds or can be prepared by known methods to the person skilled in the art.
  • Compounds of formula XVII may be oxidised as described in 16).
  • amine of formula (IV) and (X) may be obtained from compounds of formula (XVIII) and (XIX) wherein each X B is independently hydroxy, halogen or a leaving group such as mesylate, tosylate or triflate.
  • Compounds of formula (XVIII) and (XIX) are either known compounds or can be prepared by known methods to the person skilled in the art.
  • Protecting a crop of useful plants from insects, acarines, nematodes or molluscs means e.g. controlling the population of insects, acarines, nematodes or molluscs in said crop of useful plants, e.g. such that the population of said insects, acarines, nematodes or molluscs is less than would be present in the absence of said compound, preferably significantly less, e.g. at least 5, 10, 15, 20, 25, 30, 35, 40, 45 50, 55, 60, 65, 70, 75, 80, 85, 90, 95 or even at least 99% less than in the absence of said compound.
  • the compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests.
  • the pests which may be combated and controlled by the use of the compounsd of the invention include those pests associated with agriculture (which term includes the growing of crops for food and fiber products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).
  • the compounds of the invention may be used for example on turf, ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like.
  • Compositions comprising the compound of formula I may be used on ornamental garden plants (e.g.
  • compositions comprising the compound of formula I may be used on garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), on indoor plants (e.g. flowers and shrubs) and on indoor pest e.g. to control aphids, whitefly, scales, meelybug, beetles and caterpillars.
  • the compounds of the invention may be effective against harmful insects, without substantially imposing any harmful side effects to cultivated plants.
  • Application of the compounds of the invention may increase the harvest yields, and may improve the quality of the harvested material.
  • the compounds of the invention may have favourable properties with respect to amount appled, residue formulation, selectivity, toxicity, production methodology, high activity, wide spectrum of control, safety, control of resistant organisms, e.g. pests that are resistant to organic phosphorus agents and/or carbamate agents.
  • pest species which may be controlled by the compounds of formula (I) include: coleopterans, for example, Callosobruchus chinensis, Sitophilus zeamais, Tribolium castaneum,
  • Epilachna vigintioctomaculata Agriotes fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Monochamus alternatus, Lissorhoptrus oryzophilus, Lyctus bruneus, Aulacophora femoralis; lepidopterans, for example, Lymantria dispar, Malacosoma neustria), Pieris rapae,
  • nematodes for example, Meloidogyne incognita, Bursaphelenchus lignicolus Mamiya et Kiyohara, Aphelenchoides besseyi, Heterodera glycines, Pratylenchus spp..
  • Examples of further pest species which may be controlled by the compounds of formula (I) include: from the order of the Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., 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., Hyal
  • Pentomidae Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; from the order of the Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp.,
  • Pemphigus spp. Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictoce
  • Hymenoptera for example, Diprion spp., Hoplocampa spp., Lasius spp., Mono- morium pharaonis, Vespa spp.; from the order of the Isopoda, for example, Armadillidium vulgar e, Oniscus asellus, Porcellio scaber; from the order of the Isoptera, for example, Reticulitermes spp., Odontotermes spp.; from the order of the Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumifer
  • Orthoptera for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria; from the order of the Siphonaptera, for example, Ceratophyllus spp., Xenopsylla cheopis.
  • Symphyla for example, Scutigerella immaculata
  • Thysanoptera for example, Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Thysanura for example, Lepisma saccharina.
  • the phytoparasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp.,
  • Tylenchorhynchus spp. Tylenchulus spp.
  • Tylenchulus semipenetrans Tyiphinema spp.
  • the compounds of the invention may be used to control the following pest spcies: Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp. (capsids), Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper), Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp. (stinkbugs), Frankliniella occidentalis (thrip), Thrips spp.
  • Kalotermitidae for example Neotermes spp.
  • the Rhinotermitidae for example Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis
  • the Termitidae for example Globitermes sulfureus
  • Solenopsis geminata fire ant
  • Monomorium pharaonis pharaoh's ant
  • Damalinia spp. and Linognathus spp. biting and sucking lice
  • Meloidogyne spp. root knot nematodes
  • Globodera spp. and Heterodera spp. cyst nematodes
  • Pratylenchus spp. lesion nematodes
  • Rhodopholus spp. banana burrowing nematodes
  • Tylenchulus spp. citrus nematodes
  • Haemonchus contortus barber pole worm
  • Caenorhabditis eelworm Trichostrongylus spp.
  • Trichostrongylus spp. gastro intestinal nematodes
  • Deroceras reticulatum slug
  • the compound of formula I may be used for pest control on various plants, including soybean (e.g. in some cases 10-70g/ha), corn (e.g. in some cases 10-70g/ha), sugarcane (e.g. in some cases 20- 200g/ha), alfalfa (e.g. in some cases 10-70g/ha), brassicas (e.g. in some cases 10-50g/ha), oilseed rape (e.g. canola) (e.g. in some cases 20-70g/ha), potatoes (including sweet potatoes) (e.g. in some cases 10- 70g/ha), cotton (e.g. in some cases 10-70g/ha), rice (e.g. in some cases 10-70g/ha), coffee (e.g.
  • citrus e.g. in some cases 60-200g/ha
  • almonds e.g. in some cases 40-180g/ha
  • fruiting vegetables cucurbits and pulses (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.) (e.g. in some cases 10-80g/ha)
  • tea e.g. in some cases 20-150g/ha
  • bulb vegetables e.g. onion, leek etc.
  • grapes e.g. in some cases 30-180g/ha
  • pome fruit e.g. apples, pears etc.
  • stone fruit e.g. pears, plums etc.
  • the compounds of the invention may be used for pest control on various plants, including soybean, corn, sugarcane, alfalfa, brassicas, oilseed rape (e.g. canola), potatoes (including sweet potatoes), cotton, rice, coffee, citrus, almonds, fruiting vegetables, cucurbits and pulses (e.g. tomatoes, pepper, chili, eggplant, cucumber, squash etc.), tea, bulb vegetables (e.g. onion, leek etc.), grapes, pome fruit (e.g. apples, pears etc.), stone fruit (e.g. pears, plums etc.), and cereals.
  • the compounds of the invention may be used on soybean to control, for example, Elasmopalpus lignosellus, Diloboderus abderus, Diabrotica speciosa, Trialeurodes spp., Bemisia spp., aphids,
  • Sternechus subsignatus Formicidae, Agrotis ypsilon, Julus spp., Murgantia spp., Halyomorpha spp., Thyanta spp., Megascelis ssp., Procornitermes ssp., Gryllotalpidae, Nezara viridula, Piezodorus spp., Acrosternum spp., Neomegalotomus spp., Cerotoma trifurcata, PopilUa japonica, Edessa spp., Liogenys fuscus, stalk borer, Scaptocoris castanea, phyllophaga spp., Migdolus spp., Pseudoplusia includens, Anticarsia gemmatalis, Epinotia spp., Rachiplusia spp., Spodoptera spp.
  • the compounds of the invention are preferably used on soybean to control Diloboderus abderus, Diabrotica speciosa, Trialeurodes spp., Bemisia spp., Nezara viridula, Piezodorus spp., Acrosternum spp., Cerotoma trifurcata, Popillia japonica, Euschistus heros, Scaptocoris castanea, phyllophaga spp., Migdolus spp., Agriotes spp., Euschistus spp..
  • the compounds of the invention may be used on corn to control, for example, Euschistus spp. (e.g. Euschistus heros), Dichelops furcatus, Diloboderus abderus, Thyanta spp., Elasmopalpus lignosellus, Halyomorpha spp., Spodoptera frugiperda, Nezara viridula, Cerotoma trifurcata, Popillia japonica, Agrotis ypsilon, Diabrotica speciosa, aphids, Heteroptera, Procornitermes spp., Scaptocoris castanea, Formicidae, Julus ssp., Dalbulus maidis, Diabrotica spp.
  • Euschistus heros e.g. Euschistus heros
  • Dichelops furcatus Diloboderus abderus
  • Thyanta spp. Elasmopalpus lignose
  • the compounds of the invention are preferably used on corn to control Euschistus spp., (e.g. Diabrotica virgifera), Mods latipes, Bemisia tabaci, heliothis spp., Tetranychus spp., thrips spp., phyllophaga spp., Migdolus spp., scaptocoris spp., Liogenys fuscus, Spodoptera spp., Ostrinia spp., Sesamia spp., wireworms, Agriotes spp., Halotydeus destructor.
  • the compounds of the invention are preferably used on corn to control Euschistus spp., (e.g.
  • Diabrotica spp. e.g. Diabrotica speciosa, Diabrotica virgifera
  • Tetranychus spp. Thrips spp.
  • Phyllophaga spp. Migdolus spp.
  • Scaptocoris spp. Agriotes spp..
  • the compounds of the invention may be used on sugar cane to control, for example,
  • Sphenophorus spp. termites, Migdolus spp., Diloboderus spp., Telchin licus, Diatrea saccharalis, Mahanarva spp., Mealybugs, Chilo spp.
  • the compounds of the invention may be used on alfalfa to control, for example, Hypera brunneipennis, Hypera postica, Colias eurytheme, Collops spp., Empoasca solana, Epitrix spp., Geocoris spp., Lygus hesperus, Lygus lineolaris, Spissistilus spp., Spodoptera spp., Aphids, Trichoplusia ni.
  • the compounds of the invention are preferably used on alfalfa to control Hypera brunneipennis, Hypera postica, Empoasca solana, Epitrix spp., Lygus hesperus, Lygus lineolaris, Trichoplusia ni.
  • the compounds of the invention may be used on brassicas to control, for example, Chrysodeixis spp., Plutella xylostella, Pieris spp. (e.g. Pieris brassicae, Pieris rapae, Pieris napi), Mamestra spp. (e.g. Mamestra brassicae), Plusia spp., Trichoplusia spp. (e.g. Trichoplusia ni), Phyllotreta spp. (e.g.
  • the compounds of the invention are preferably used on brassicas to control Plutella xylostella, Pieris spp., Plusia spp., Trichoplusia ni, Phyllotreta spp., Thrips spp., Chaetocnema spp..
  • the compounds of the invention may be used on oil seed rape, e.g. canola, to control, for example, Meligethes spp. (e.g. Meligethes aeneus), Ceutorhynchus spp., (e.g. Ceutorhynchus assimilis, Ceutorhynchus napi), Halotydeus destructor, Psylloides spp. (e.g. PsylUodes chrysocephala), Phyllotreta spp. (e.g. Phyllotreta cruciferae, Phyllotreta striolata), Chaetocnema spp..
  • Meligethes spp. e.g. Meligethes aeneus
  • Ceutorhynchus spp. e.g. Ceutorhynchus assimilis, Ceutorhynchus napi
  • the compounds of the invention may be used on potatoes, including sweet potatoes, to control, for example, Empoasca spp., Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Maladera matrida, Agriotes spp., Aphids, wireworms.
  • the compounds of the invention are preferably used on potatoes, including sweet potatoes, to control Empoasca spp., Leptinotarsa spp., Diabrotica speciosa, Phthorimaea spp., Paratrioza spp., Agriotes spp..
  • the compounds of the invention may be used on cotton to control, for example, Anthonomus grandis, Pectinophora spp., heliothis spp., Spodoptera spp., Tetranychus spp. (e.g. Tetranychus urticae), Empoasca spp., Thrips spp. (e.g. Thrips tabaci, Thrips palmi), Bemisia tabaci, Trialeurodes spp., Aphids, Lygus spp. (e.g.
  • Polyphagotarsonemus latus The compounds of the invention are preferably used on cotton to control Anthonomus grandis, Tetranychus spp., Empoasca spp., thrips spp., Lygus spp., phyllophaga spp., Scaptocoris spp..
  • the compounds of the invention may be used on rice to control, for example, Leptocorisa spp. (e.g. Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta), Cnaphalocrosis spp., Chilo spp. (e.g. Chilo suppressalis, Chilo polychrysus, Chilo auricilius), Scirpophaga spp. (e.g. Scirpophaga incertulas, Scirpophaga innotata, Scirpophaga surfacela), Lissorhoptrus spp., Oebalus pugnax,
  • Leptocorisa spp. e.g. Leptocorisa oratorius, Leptocorisa chinensis, Leptocorisa acuta
  • Cnaphalocrosis spp. e.g. Chilo suppressalis, Chilo poly
  • Scotinophara spp. e.g. Scotinophara coarctata, Scotinophara lurida, Scotinophara latiuscula
  • Nephotettix spp. e.g. Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens, Nephotettix cincticeps), Mealybugs, Sogatella furcifera, Nilaparvata lugens, OrseoUa spp. (e.g. OrseoUa oryzae), Cnaphalocrocis medinalis, Marasmia spp. (e.g.
  • the compounds of the invention are preferably used on rice to control Leptocorisa spp., Lissorhoptrus spp., Oebalus pugnax, Nephotettix spp.(e.g.
  • the compounds of the invention may be used on coffee to control, for example, Hypothenemus spp. (e.g. Hypothenemus Hampei), Perileucoptera Coffeella, Tetranychus spp., Brevipalpus spp., Mealybugs.
  • Hypothenemus spp. e.g. Hypothenemus Hampei
  • Perileucoptera Coffeella e.g. Tetranychus spp.
  • Brevipalpus spp. e.g. Hypothenemus Hampei
  • the compounds of the invention are preferably used on coffee to control Hypothenemus Hampei, Perileucoptera Coffeella.
  • the compounds of the invention may be used on citrus to control, for example,
  • Panonychus citri Phyllocoptruta oleivora
  • Brevipalpus spp. e.g. Brevipalpus californicus, Brevipalpus phoenicis
  • Diaphorina citri e.g. Scirtothrips spp.
  • Scirtothrips dorsalis e.g. Scirtothrips dorsalis
  • Thrips spp. Unaspis spp., Ceratitis capitata
  • Phyllocnistis spp. e.g. Phyllocnistis citrella
  • Aphids Hardscales, Softscales, Mealybugs.
  • the compounds of the invention are preferably used on citrus to control Panonychus citri, Phyllocoptruta oleivora, Brevipalpus spp., Diaphorina citri, Scirtothrips spp., thrips spp., Phyllocnistis spp..
  • the compounds of the invention may be used on almonds to control, for example, Amyelois transitella, Tetranychus spp.
  • the compounds of the invention may be used on fruiting vegetables, cucurbits and pulses, including tomatoes, pepper, chili, eggplant, cucumber, squash etc., to control, for example, Thrips spp., Tetranychus spp. (e.g. Tetranychus urticae)., Polyphagotarsonemus spp. (e.g. Polyphagotarsonemus latus), Aculops spp. (e.g. Aculops lycopersici), Empoasca spp. (e.g. Empoasca fabae), Spodoptera spp., heliothis spp., Tuta absoluta, Liriomyza spp. (e.g.
  • Paratrioza spp. Frankliniella spp. (e.g. Frankliniella occidentalis, Frankliniella intonsa, Frankliniella bispinosa), Spodoptera spp. (e.g. Spodoptera exigua, Spodoptera littoralis, Spodoptera litura, Spodoptera frugiperda, Spodoptera eridanid), Anthonomus spp., Phyllotreta spp., Amrasca spp. (e.g. Amrasca biguttula biguttuld), Epilachna spp., Halyomorpha spp., Scirtothrips spp., Leucinodes spp. (e.g.
  • Neoleucinodes orbonalis Leucinodes orbonalis
  • Neoleucinodes spp. e.g. Neoleucinodes elegantalis
  • Maruca spp. Fruit flies, Stinkbugs, Lepidopteras, Coleopteras, Helicoverpa spp. (e.g. Helicoverpa armigera), Heliothis spp. (e.g. Heliothis virescens), Paratrioza spp. (e.g.
  • the compounds of the invention are preferably used on fruiting vegetables, cucurbits and pulses, including tomatoes, pepper, chili, eggplant, cucumber, squash etc., to control Thrips spp., Tetranychus spp., Polyphagotarsonemus spp., Aculops spp., Empoasca spp., Spodoptera spp., heliothis spp., Tuta absolutea, Liriomyza spp., Paratrioza spp.,
  • the compounds of the invention may be used on tea to control, for example, Pseudaulacaspis spp., Empoasca spp., Scirtothrips spp., Caloptilia theivora, Tetranychus spp..T e compounds of the invention are preferably used on tea to control Empoasca spp., Scirtothrips spp..
  • the compounds of the invention may be used on bulb vegetables, including onion, leek etc. to control, for example, Thrips spp., Spodoptera spp., heliothis spp..
  • the compounds of the invention are preferably used on bulb vegetables, including onion, leek etc. to control Thrips spp..
  • the compounds of the invention may be used on grapes to control, for example, Empoasca spp.,
  • Lobesia spp. Eupoecilia ambiguella, Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Eotetranychus Willamettei, Erythroneura Elegantula, Scaphoides spp., Scelodonta strigicollis, Mealybugs.
  • the compounds of the invention are preferably used on grapes to control Frankliniella spp., Thrips spp., Tetranychus spp., Rhipiphorothrips Cruentatus, Scaphoides spp..
  • the compounds of the invention may be used on pome fruit, including apples, pears etc., to control, for example, Cacopsylla spp., Psylla spp., Panonychus ulmi, Cydia pomonella, Lepidopteras, Aphids, Hardscales, Softscales.
  • the compounds of the invention are preferably used on pome fruit, including apples, pears etc., to control Cacopsylla spp., Psylla spp., Panonychus ulmi.
  • the compounds of the invention may be used on stone fruit to control, for example, Grapholita molesta, Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp., Aphids, Hardscales, Softscales, Mealybugs.
  • the compounds of the invention are preferably used on stone fruit to control Scirtothrips spp., Thrips spp., Frankliniella spp., Tetranychus spp..
  • the compounds of the invention may be used on cereals to control, for example, Aphids,
  • Stinkbugs earthmites, Eurygaster integriceps, Zabrus tenebrioides, Anisoplia austriaca, Chaetocnema aridula, Phyllotreta spp., Oulema melanopus, Oscinella spp., Delia spp., Mayetiola spp., Contarinia spp., Cephus spp., Steneotarsonemus spp., Apamea spp..
  • compounds of formula I may be used on rice to control Baliothrips biformis (Thrips), Chilo spp. (e.g. Chilo polychrysus (Dark headed striped borer), Chilo suppressalis (Rice stemborer), Chilo indicus (Paddy stem borer), Chilo polychrysus (Dark-headed rice borer), Chilo suppressalis (Stripe stem borer)), Cnaphalocrocis medinalis (Rice leaf folder), Dicladispa armigera (Hispa), Hydrellia philipina (Rice whorl-maggot), Laodelphax spp. (Smaller brown planthopper) (e.g.
  • Laodelphax striatellus Laodelphax striatellus ), Lema oryzae (Rice leaf eetle), Leptocorsia acuta (Rice bug), Leptocorsia oratorius (rice bug), Lissorhoptrus oryzophilus (rice water weevil), Mythemina separata (armyworm), Nephottetix spp. (Green leafhopper ) (e.g.
  • Nephotettix cincticeps Nephotettix malayanus, Nephotettix nigropictus, Nephotettix parvus, Nephottetix virescens), Nilaparvata lugens (Brown Planthopper), Nymphula depunctalis (Rice caseworm), Orseolia oryzae (Rice Gall midge), Oulema oryzae (Rice leafbeetle), Scirpophaga incertulas (Yellow Stemborer), Scirpophaga innotata (White Stemborer), Scotinophara coarctata (Rice black bug), Sogaella frucifera (White-backed planthopper),
  • the compounds of the invention may be used to control animal housing pests including: Ants, Bedbugs (adult), Bees, Beetles, Boxelder Bugs, Carpenter Bees, Carpet Beetles, Centipedes, Cigarette, Beetles, Clover Mites, Cockroaches, Confused Flour Beetle, Crickets, Earwigs, Firebrats, Fleas, Flies, Lesser Grain Borers, Millipedes, Mosquitoes, Red Flour Beetles, Rice Weevils, Saw-toothed Grain Beetles, Silverfish, Sowbugs, Spiders, Termites, Ticks, Wasps, Cockroaches, Crickets, Flies, Litter Beetles (such as Darkling, Hide, and Carrion), Mosquitoes, Pillbugs, Scorpions, Spiders, Spider Mites (Twospotted, Spruce), Ticks.
  • the compounds of the invention may be used to control ornamental pests including: Ants (Including Imported fire ants), Armyworms, Azalea caterpillars, Aphids, Bagworms, Black vine weevils (adult), Boxelder bugs, Budworms, California oakworms, Cankerworms, Cockroaches, Crickets, Cutworms, Eastern tent caterpillars, Elm leaf beetles, European sawflies, Fall web worms, Flea beetles, Forest tent caterpillars, Gypsy moth larvae, Japanese beetles (adults), June beetles (adults), Lace bugs, Leaf- feeding caterpillars, Leafhoppers, Leafrniners (adults), Leaf rollers, Leaf skeletonizers, Midges, Mosquitoes, Oleander moth larvae, Pillbugs, Pine sawflies, Pine shoot beetles, Pinetip moths, Plant bugs, Root weevils, Sawflies, Scale insects (crawlers), Spiders, Spittlebug
  • the compounds of formula (I), in particular those in the tables above, may be used for soil applications, including as a seed application, to target at least the following: sucking pests such as aphids, thrips, brown plant hopper (e.g. on rice), sting bugs, white flies (e.g. on cotton and vegetables), mites; on soil pests such as corn root worm, wireworms, white grubs, zabrus, termites (e.g. on sugar cane, soy, pasture), maggots, cabbage root fly, red legged earth mite; on lepidoptera, such as spodoptera, cutworms, elasmoplpus , plutella (e.g.
  • brassica stem borers, leaf miners, flea beetle, Sternechus; on nematicides, such as Heterodera glycines (e.g. on soybean), Pratylenchus brachyurus (e.g. on corn), P. zeae (e.g. oncorn), P. penetrans (e.g. on corn), Meloidogyne incognita (e.g. on vegetables), Heterodera schachtii (e.g. on sugar beet), Rotylenchus reniformis (e.g. on cotton), Heterodera avenae (e.g. on cereals), Pratylenchus neglectus (e.g. on cereals), thornei (e.g. on cereals).
  • Heterodera glycines e.g. on soybean
  • Pratylenchus brachyurus e.g. on corn
  • P. zeae e.g.
  • the compounds of formula (I), in particular those in the tables above may be used for seed applications at least on the following: soil grubs for corn, soybeans, sugarcane: Migdolus spp;
  • Sphenophorus levis & Metamasius hemipterus Sphenophorus levis & Metamasius hemipterus; termites for soybeans, sugarcane, pasture, others:
  • Heterotermes tenuis Heterotermes longiceps
  • Cornitermes cumulans Procornitermes triacifer ;
  • Neocapritermes opacus Neocapritermes parvus
  • corn root worms for corn and potatoes Diabrotica spp., seed Maggot: Delia platura; soil stinkbugs: Scaptocoris castanea; wireworms: Agriotes spp; Athous spp Hipnodes bicolor; Ctenicera destructor; Limonius canu; Limonius californicus; rice water weevil:
  • Lissorhoptrus oryzophilus Red Legged earth mites: Halotydeus destructor.
  • the invention therefore provides a method of combating and/or controlling an animal pest, e.g. an invertebrate animal pest, which comprises applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (I).
  • an animal pest e.g. an invertebrate animal pest
  • applying to the pest to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (I).
  • the invention provides a method of combating and/or controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a pest, a locus of pest, preferably a plant, or to a plant susceptible to attack by a pest,
  • the compounds of formula (I) are preferably used against insects, acarines or nematodes.
  • plants as used herein includes seedlings, bushes and trees. Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering.
  • herbicides or classes of herbicides e.g. ALS-, GS-, EPSPS-, PPO- and HPPD-inhibitors
  • crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate- resistant maize varieties commercially available under the trade names RoundupReady® and
  • Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • the plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • Treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on their surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on, injecting and, in the case of propagation material, in particular in the case of seed, also by applying one or more coats.
  • Compounds of formula I may be used on transgenic plants (including cultivars) obtained by genetic engineering methods and/or by conventional methods. These are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive "synergistic") effects.
  • the preferred transgenic plants or plant cultivars which are to be treated according to the invention include all plants which, by virtue of the genetic modification, received genetic material which imparts particularly advantageous, useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products.
  • transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soybean, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Compounds of formula I may be used on transgenic plants that are capable of producing one or more pesticidal proteins which confer upon the transgenic plant tolerance or resistance to harmful pests, e.g. insect pests, nematode pests and the like.
  • pesticidal proteins include, without limitation, Cry proteins from Bacillus thuringiensis CrylAb, CrylAc, CrylF, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C; engineered proteins such as modified Cry3A ( US Patent 7,030,295) or CrylA.105; or vegetative insecticidal proteins such as Vipl, Vip2 or Vip3.
  • Cry proteins from Bacillus thuringiensis CrylAb, CrylAc, CrylF, Cry2Ab, Cry2Ae, Cry3A, Cry3Bb, or Cry9C engineered proteins such as modified Cry3A ( US Patent 7,030,295) or CrylA.105
  • vegetative insecticidal proteins such as Vipl, Vip2 or Vip3.
  • Bt Cry proteins and VIPs useful in the invention can be found on the worldwide web at Bacillus thuringiensis Toxin Nomenclature Database maintained by the University of
  • pesticidal proteins useful in the invention include proteins of bacteria colonizing nematodes, e.g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome- inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ec
  • pesticidal proteins or transgenic plants capable of synthesizing such proteins are disclosed, e.g., in EP-A 374753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451878, WO 03/18810 and WO 03/52073.
  • Agrisure®CB (PI) (corn producing CrylAb), Agrisure®RW (P2) (corn producing mCry3A), Agrisure® Viptera (P3) (corn hybrids producing Vip3Aa); Agrisure300GT (P4) (corn hybrids producing CrylAb and mCry3A); YieldGard® (P5) (corn hybrids producing the CrylAb protein), YieldGard® Plus (P6) (corn hybrids producing CrylAb and Cry3Bbl), Genuity® SmartStax® (P7) (corn hybrids with CrylA.105, Cry2Ab2, CrylF, Cry34/35, Cry3Bb) ; Herculex® I (P8) (corn hybrids producing CrylFa) and Herculex®RW (P9) (corn hybrids producing Cry34Abl, Cry35Abl and the enzyme Phosphinothricin-N-
  • transgenic crops are:
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10 (PI 8). Maize which has been rendered insect-resistant by transgenic expression of a modified CrylllA toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-D-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-l 150 Brussels, Belgium, registration number C/DE/02/9 (P19). MON 863 expresses a CrylllB(bl) toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,
  • NK603 ⁇ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylA(b) toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • transgenic plants and of very high interest, are those carrying traits conferring resistance to 2.4D (e.g. Enlist®) (e.g. WO 2011066384) (P23), glyphosate (e.g. Roundup Ready® (P24), Roundup Ready 2 Yield® (P25)), sulfonylurea (e.g. STS®) (P26), glufosinate (e.g.
  • soybean plants carrying trains conferring resistance to 2.4D e.g. Enlist®
  • glyphosate e.g.
  • sulfonylurea e.g. STS®
  • glufosinate e.g. Liberty Link®, Ignite®
  • Dicamba e.g. isoxaflutole herbicide
  • Double or triple stack in soybean plants of any of the traits described here are also of interest, including glyphosate and sulfonyl-urea tolerance (e.g. Optimum GAT®, plants stacked with STS® and Roundup Ready® or Roundup Ready 2 Yield®), dicamba and glyphosate tolerance (Monsanto).
  • a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA).
  • SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting).
  • compositions both solid and liquid formulations
  • the composition is generally used for the control of pests such that a compound of formula (I) is applied at a rate of from 0.1 g to 10kg per hectare, preferably from 1 g to 6kg per hectare, more preferably from lg to 1kg per hectare.
  • a compound of formula (I) When used in a seed dressing, a compound of formula (I) is generally used at a rate of O.OOOlg to lOg (for example O.OOlg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.
  • the present invention provides a composition
  • molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) and a suitable carrier or diluent therefor.
  • the composition is preferably an insecticidal, acaricidal, nematicidal or molluscicidal composition.
  • compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations.
  • the formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (I).
  • Dustable powders may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
  • solid diluents for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulfur, lime, flours, talc and other organic and inorganic solid carriers
  • Soluble powders may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water
  • water-soluble inorganic salts such as sodium bicarbonate, sodium carbonate or magnesium sulfate
  • water-soluble organic solids such as a polysaccharide
  • compositions may also be granulated to form water soluble granules (SG).
  • WP Wettable powders
  • WG Water dispersible granules
  • Granules may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulfates or phosphates) and drying if necessary.
  • a hard core material such as sands, silicates, mineral carbonates, sulfates or phosphates
  • Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils).
  • solvents such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters
  • sticking agents such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils.
  • One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
  • DC Dispersible Concentrates
  • a compound of formula (I) may be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether.
  • organic solvent such as a ketone, alcohol or glycol ether.
  • surface active agent for example to improve water dilution or prevent crystallization in a spray tank.
  • Emulsifiable concentrates or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents).
  • Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVES SO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as Cg-Qo fatty acid dimethylamide) and chlorinated hydrocarbons.
  • aromatic hydrocarbons such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVES SO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark
  • ketones such as cyclo
  • An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment.
  • Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion.
  • Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.
  • Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation.
  • a compound of formula (I) is present initially in either the water or the solvent/SFA blend.
  • Suitable solvents for use in MEs include those hereinbefore described for use in ECs or in EWs.
  • An ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation.
  • An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.
  • SC Suspension concentrates
  • SCs may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I).
  • SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound.
  • One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle.
  • a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.
  • Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example « -butane).
  • a compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non- pressurized, hand-actuated spray pumps.
  • a compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.
  • Capsule suspensions may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerization stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (I) and, optionally, a carrier or diluent therefor.
  • the polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure.
  • the compositions may provide for controlled release of the compound of formula (I) and they may be used for seed treatment.
  • a compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
  • a composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of formula (I)).
  • additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (I)).
  • a compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS).
  • DS powder for dry seed treatment
  • SS water soluble powder
  • WS water dispersible powder for slurry treatment
  • CS capsule suspension
  • the preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above.
  • Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).
  • Wetting agents, dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type.
  • Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.
  • Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (for example sodium lauryl sulfate), salts of sulfonated aromatic compounds (for example sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonate and mixtures of sodium di-z ' opropyl- and tri-wopropyl-naphthalene sulfonates), ether sulfates, alcohol ether sulfates (for example sodium laureth-3 -sulfate), ether carboxylates (for example sodium laureth-3- carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and
  • Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
  • Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide);
  • alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof
  • fatty alcohols such as oleyl alcohol or cetyl alcohol
  • alkylphenols such as octylphenol, nonylphenol or octylcresol
  • partial esters derived from long chain fatty acids or hexitol anhydrides condensation products of said partial esters with ethylene oxide
  • alkanolamides alkanolamides
  • simple esters for example fatty acid polyethylene glycol esters
  • amine oxides for example lauryl dimethyl amine oxide
  • lecithins alkanolamides
  • simple esters for example fatty acid polyethylene glycol esters
  • amine oxides for example lauryl dimethyl amine oxide
  • lecithins lecithins
  • Suitable suspending agents include hydrophilic colloids (such as polysaccharides,
  • polyvinylpyrrolidone or sodium carboxymethylcellulose and swelling clays (such as bentonite or attapulgite).
  • a compound of formula (I) may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapor or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water- soluble bag) in soil or an aqueous environment.
  • a compound of formula (I) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by
  • compositions for use as aqueous preparations are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being added to water before use.
  • These concentrates which may include DCs, SCs, ECs, EWs, MEs, SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment.
  • Such aqueous preparations may contain varying amounts of a compound of formula (I) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
  • a compound of formula (I) may be used in mixtures with fertilizers (for example nitrogen-, potassium- or phosphorus-containing fertilizers). Suitable formulation types include granules of fertilizer. The mixtures preferably contain up to 25% by weight of the compound of formula (I).
  • fertilizers for example nitrogen-, potassium- or phosphorus-containing fertilizers.
  • Suitable formulation types include granules of fertilizer.
  • the mixtures preferably contain up to 25% by weight of the compound of formula (I).
  • the invention therefore also provides a fertilizer composition comprising a fertilizer and a compound of formula (I).
  • compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • the compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, e.g. a insecticide, fungicide or herbicide, or a synergist or plant growth regulator where appropriate.
  • a pesticide e.g. a insecticide, fungicide or herbicide, or a synergist or plant growth regulator where appropriate.
  • An additional active ingredient may provide a composition having a broader spectrum of activity or increased persistence at a locus; synergize the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I); or help to overcome or prevent the development of resistance to individual components.
  • suitable pesticides include the following:
  • a) Pyrethroids such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin and gamma cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin, acrinathirin, etofenprox or 5-benzyl-3-furylmethyl-(E)-(lR,3S)-2,2-dimethyl- 3-(2-oxothiolan-3-ylidenemethyl)cyclopropane carboxylate;
  • Organophosphates such as profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s -methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon; c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb,
  • Benzoyl ureas such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, diafenthiuron, lufeneron, novaluron, noviflumuron or chlorfluazuron;
  • Organic tin compounds such as cyhexatin, fenbutatin oxide or azocyclotin;
  • Pyrazoles such as tebufenpyrad, tolfenpyrad, ethiprole, pyriprole, fipronil, and fenpyroximate;
  • Macrolides such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad, azadirachtin, milbemectin, lepimectin or spinetoram;
  • Organochlorine compounds such as endosulfan (in particular alpha-endosulfan), benzene hexachloride,
  • Amidines such as chlordimeform or amitraz
  • Fumigant agents such as chloropicrin, dichloropropane, methyl bromide or metam
  • Neonicotinoid compounds such as imidacloprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, or nithiazine;
  • Diacylhydrazines such as tebufenozide, chromafenozide or methoxyfenozide
  • Diphenyl ethers such as diofenolan or pyriproxifen
  • Ketoenols such as Spirotetramat, spirodiclofen or spiromesifen
  • Diamides such as flubendiamide, chlorantraniliprole (Rynaxypyr®) or cyantraniliprole;

Abstract

La présente invention concerne des composés de formule (I) dans laquelle G1 représente de l'oxygène; R1 représente de l'hydrogène; R2 représente un groupe P, L représente une liaison, méthylène ou éthylène; l'un de A1 et A2 représente S, SO ou SO2 et l'autre représente -C(R4)R4-; R3 représente de l'hydrogène ou du méthyle; chaque R4 représente indépendamment de l'hydrogène ou du méthyle; Y1, Y2 et Y3 représentent indépendamment CH ou de l'azote; et au plus deux de Y1, Y2 et Y3 représentent de l'azote, mais Y2 et Y3 ne représentent pas tous les deux de l'azote; R5 représente chloro, bromo, fluoro; X2 représente C-X6 ou de l'azote; Χ1, Χ3 et X6 représentent indépendamment de l'hydrogène, de l'halogène ou du trihalométhyle, au moins deux de X1, X3 et X6 ne représentent pas de l'hydrogène; X4 représente du trifluorométhyle, du difluorométhyle ou du chlorodifluorométhyle. L'invention concerne également des procédés d'utilisation de ces composés pour lutter contre des insectes, des acariens, des nématodes ou des mollusques, ainsi que des intermédiaires utiles pour la synthèse de ces composés.
PCT/EP2012/065421 2011-08-25 2012-08-07 Dérivés d'isoxazoline en tant que composés insecticides WO2013026695A1 (fr)

Priority Applications (11)

Application Number Priority Date Filing Date Title
CN201280041298.XA CN103764644A (zh) 2011-08-25 2012-08-24 作为杀虫化合物的异噁唑啉衍生物
JP2014526519A JP6061934B2 (ja) 2011-08-25 2012-08-24 殺虫化合物としてのイソオキサゾリン誘導体
CN201610356475.3A CN106045962A (zh) 2011-08-25 2012-08-24 作为杀虫化合物的异噁唑啉衍生物
BR112014004235A BR112014004235A2 (pt) 2011-08-25 2012-08-24 derivados de isoxazolina como compostos inseticidas
AU2012298448A AU2012298448A1 (en) 2011-08-25 2012-08-24 Isoxazoline derivatives as insecticidal compounds
KR1020147007321A KR20140054302A (ko) 2011-08-25 2012-08-24 살곤충 화합물로서의 이속사졸린 유도체
EP12748717.1A EP2748155B1 (fr) 2011-08-25 2012-08-24 Dérivés d'isoxazoline convenant comme composés insecticides
PCT/EP2012/066554 WO2013026931A1 (fr) 2011-08-25 2012-08-24 Dérivés d'isoxazoline convenant comme composés insecticides
MX2014002092A MX2014002092A (es) 2011-08-25 2012-08-24 Derivados de isoxazolina como compuestos insecticidas.
CO14036579A CO6890111A2 (es) 2011-08-25 2014-02-21 Derivados de isoxazolina como compuestos insecticidas
CL2014000439A CL2014000439A1 (es) 2011-08-25 2014-02-24 Compuestos derivados de isoxazolina insecticidas; método para controlar insectos, acáridos, nemátodos o moluscos; método para controlar insectos, acáridos, nemátodos o moluscos que comprende aplicar a una plaga; composición insecticida acaricida

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EP11178929 2011-08-25
EP11178929.3 2011-08-25
EP11178921.0 2011-08-25
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EP12179257.6 2012-08-03
EP12179257 2012-08-03
EP12179385.5 2012-08-06
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WO2015091900A1 (fr) * 2013-12-20 2015-06-25 Intervet International B.V. Utilisation de dérivés d'isoxazoline pour le traitement ou la prévention d'infestations de la volaille par les arthropodes
WO2017050922A1 (fr) 2015-09-23 2017-03-30 Syngenta Participations Ag Benzamides à substitution isoxazoline et leurs analogues comme insecticides
WO2018039508A1 (fr) * 2016-08-25 2018-03-01 Merial, Inc. Procédé de réduction d'effets indésirables dans des traitements antiparasitaires
WO2018172471A1 (fr) 2017-03-22 2018-09-27 Syngenta Participations Ag Dérivés de cyclopropyl-méthyle amide à action pesticide
WO2018197466A1 (fr) 2017-04-26 2018-11-01 Basf Se Dérivés de succinimide substitués utilisés en tant que pesticides
US10456358B2 (en) 2013-12-20 2019-10-29 Intervet Inc. Isoxazoline compositions and use thereof in the prevention or treatment of parasite infestations in animals
EP3613736A1 (fr) 2018-08-22 2020-02-26 Basf Se Dérivés de glutarimide substitués
EP3696177A1 (fr) 2019-02-12 2020-08-19 Basf Se Composés hétérocycliques destinés à la lutte contre les organismes nuisibles invertébrés
CN112174904A (zh) * 2019-07-01 2021-01-05 沈阳化工大学 一种异噁唑啉类化合物及其应用
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RU2796536C2 (ru) * 2013-12-20 2023-05-25 Интервет Интернэшнл Б.В. Применение изоксазолиновых соединений на домашней птице

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