WO2016155831A1 - Dérivés d'isoxazoline-styrène utilisés comme composés insecticides - Google Patents

Dérivés d'isoxazoline-styrène utilisés comme composés insecticides Download PDF

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WO2016155831A1
WO2016155831A1 PCT/EP2015/057289 EP2015057289W WO2016155831A1 WO 2016155831 A1 WO2016155831 A1 WO 2016155831A1 EP 2015057289 W EP2015057289 W EP 2015057289W WO 2016155831 A1 WO2016155831 A1 WO 2016155831A1
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Girish RAWAL
Raghu Ramaiah
Myriem El Qacemi
Jérôme Yves CASSAYRE
Torsten LUKSCH
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Syngenta Participations Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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 styrene 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.
  • P is nitro, amino, R oxycarbonyl, P1 , P2 or P3;
  • a 1 , A 2 , A 3 , A 4 and A 5 are independently of each other C-H, C-R 5 , or nitrogen and at least one of A 1 or A 5 is C-P;
  • G is oxygen or sulfur
  • R is hydrogen, Ci-C 8 alkyl, d-C 8 alkoxy-, Ci-C 8 alkylcarbonyl-, C 3 -C 8 cycloalkylcarbonyl or d- C 8 alkoxycarbonyl-;
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , six to fourteen ring-membered aryl-Ci-C 4 alkylene- or six to fourteen ring-membered aryl-Ci-C 4 alkylene- wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 , six to fourteen ring-membered aryl or six to fourteen ring- membered aryl substituted by one to five R 8 ,
  • R and R 2 is (R 2a )( R )N- or R and R 2 form a four to six membered ring together with the atoms to which they are attached substituted by one to five R 6
  • R 2a is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , six to fourteen ring-membered aryl-Ci-C 4 alkylene- or six to fourteen ring-membered aryl-Ci-C 4 alkylene- wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- wherein the five to ten ring-
  • X 1 , and X 2 are independently of each other H, halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, d- C 8 alkenyl, Ci-C 8 haloalkenyl, Ci-C 8 alkynyl, Ci-C 8 haloalkynyl, C 3 -Ci 0 cycloalkyl, Ci-C 8 alkoxy-, d- C 8 haloalkoxy-, Ci-C 8 alkylthio-, Ci-C 8 haloalkylthio-, Ci-C 8 alkylsulfinyl-, Ci-C 8 haloalkylsulfinyl-, d- C 8 alkylsulfonyl-, or Ci-C 8 haloalkylsulfonyl);
  • R 3 is d-C 8 haloalkyl
  • R 4 is six to fourteen ring-membered aryl or six to fourteen ring-membered aryl substituted by one to five R 9 , or heterosix to fourteen ring-membered aryl or heterosix to fourteen ring-membered aryl substituted by one to five R 9 ;
  • each R 5 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, Ci-C 8 alkenyl, d- C 8 haloalkenyl, d-dalkynyl, d-C 8 naloalkynyl, d-docycloalkyl, d-dalkoxy-, d-dhaloalkoxy-, d- dalkylthio-, d-dhaloalkylthio-, d-dalkylsulfinyl-, d-dhaloalkylsulfinyl-, d-C 8 alkylsulfonyl-, or d- dhaloalkylsulfonyl-;
  • each R 6 is independently halogen, cyano, nitro, hydroxy, amino, d-C 8 alkylamino, (d- dalkyl ⁇ amino, d-dalkylcarbonylamino, d-dhaloalkylcarbonylamino, d-dalkoxy-, d- dhaloalkoxy-, six to fourteen ring-membered aryloxy or six to fourteen ring-membered aryloxy substituted by one to five R 0 , six to fourteen ring-membered aryloxy-d-dalkylene or six to fourteen ring-membered aryloxy-d-dalkylene wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 0 , d-C 8 alkylcarbonyl-, d-C 8 alkoxycarbonyl-, mercapto, d-C 8 alkylthio-, d-C 8 haloal
  • each R 8 is independently halogen, cyano, nitro, oxo, d-dalkyl, d-C 8 haloalkyl, d-dcyanoalkyl, C 2 - dalkenyl, C 2 -C 8 naloalkenyl, d-dalkynyl, d-dhaloalkynyl, d-Ci 0 cycloalkyl, d-Ciocycloalkyl-Ci- dalkylene, hydroxy, d-dalkoxy-, d-dhaloalkoxy-, mercapto, d-C 8 alkylthio-, d-dhaloalkylthio-, Crdalkylsulfinyl-, d-dhaloalkylsulfinyl-, d-C 8 alkylsulfonyl-, d-dhaloalkylsulfonyl-, Ci- d
  • each R 9 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -
  • each R 0 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy-, or d-
  • 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 compounds of the invention may contain one or more asymmetric carbon atoms, for example, at the -CR 3 R 4 - group, and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such.
  • the number of substituents does not exceed the number of available C-H and N-H bonds, for example in the group Ci-C 8 alkyl substituted by one to five R 6 has only one to three substituents if dalkyl thus methyl is meant.
  • 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 Ci-C 4 , most preferably C1-C3 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 Ci-C 3 , more preferably Ci-C 2 , most preferably Ci 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)-configu ration. 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 -C 6 , more preferably C 2 -C 4 , 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, 1 -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, [1 ,3]dioxolanyl, piperidinyl, piperazinyl,
  • bicyclic groups include 2,3-dihydro-benzofuranyl, benzo[1 ,4]dioxolanyl, benzo[1 ,3]dioxolanyl, chromenyl, and 2,3-dihydro-benzo[1 ,4]dioxinyl.
  • the five to ten ring-membered heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.
  • Preferred values of, P, A 1 , A 2 , A 3 , A 4 ,A 5 , X 1 , X 2 , G, Z, R , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 0 are, in any combination, as set out below.
  • P is P1 ,
  • no more than two of A 1 , A 2 , A 3 , A 4 and A 5 are nitrogen, more preferably no more than one of A 1 , A 2 , A 3 , A 4 and A 5 is nitrogen.
  • a 1 is C-H, C-R 5 or C-P and at least one of A 1 or A 5 is C-P, more preferably A 1 is C-H, C-R 5 .
  • a 2 is C-H or C-R 5 , more preferably A 2 is C-H.
  • a 3 is C-H or C-R 5 , more preferably A 3 is C-H.
  • a 4 is C-H or C-R 5 , most preferably A 4 is C-H.
  • a 5 is C-H, C-R 5 or C-P and at least one of A 1 or A 5 is C-P, more preferably A 5 is C-P
  • a 1 is C-R 5 , A 2 is C-H, A 3 is C-H or nitrogen and A 4 is C- H or nitrogen and A 5 is C-P;
  • a 1 is C-P
  • a 2 is C-H
  • a 3 is C-H
  • a 4 is C-H
  • a 5 is C-H or C-R 5 ;
  • P is P1 ;
  • P is P2;
  • P is P3;
  • P is P1 ;
  • G is oxygen
  • X 1 , and X 2 are independently hydrogen, halogen, cyano, d-C 8 alkyl, d- C 8 haloalkyl or C 3 -C 8 cycloalkyl; more preferabyl hydrogen, halogen, d-C 8 alkyl or Ci-C 8 haloalkyl, more preferably hydrogen, halogen, d-C 4 alkyl or d-C 4 haloalkyl, even more preferably hydrogen, halogen, d-C 2 alkyl or d-C 2 haloalkyl, yet even more preferably hydrogen, methyl, chloro, bromo or trifluoromethyl; most preferably X 1 and X 2 are both hydrogen.
  • R is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 - docycloalkyl substituted by one to five R 7 , six to fourteen ring-membered aryl-d-C 4 alkylene- or six to fourteen ring-membered aryl-d-C 4 alkylene- wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 , six to fourteen ring-membered aryl or six to fourteen ring- membered aryl substituted by one to five R 8 , five to
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , six to fourteen ring-membered aryl-Ci-C 4 alkylene- or six to fourteen ring-membered aryl-Ci-C 4 alkylene- wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 , six to fourteen ring-membered aryl or six to fourteen ring- membered aryl substituted by one to five R 8
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , six to fourteen ring-membered aryl-Ci-C 4 alkylene- or six to fourteen ring-membered aryl-Ci-C 4 alkylene- wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 , six to fourteen ring-membered aryl or six to fourteen ring- membered aryl substituted by one to five R 8
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C 3 - C-iocycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , six to fourteen ring-membered aryl-d- C 4 alkylene- or six to fourteen ring-membered aryl-Ci-C 4 alkylene- wherein the six to fourteen ring- membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-d- C 4 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- wherein the five to ten ring- membered heterocyclyl moiety is substituted by one to five R 8 , six to fourteen ring-membered aryl or six to fourteen ring-membered aryl substituted by one to five R 8 ,
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , d-docyclo- alkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , phenyl-Ci-C 4 alkylene- or phenyl-d- C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Ci-C 4 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , tetrahydrofuranyl- Ci-C 4 alkylene- or tetrahydrofuranyl-Ci-C 4 alkylene- wherein the tetrahydrofuranyl moiety is substituted by one to five R 8 , imidazolyl-Ci-C 4 alkylene- or imidazolyl-
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C 3 - C-iocycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , phenyl-Ci-C 4 alkylene- or phenyl-d- C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Ci-C 4 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , oxetanyl or oxetanyl substituted by one to five R 8 , thietanyl-Ci-C 4 alkylene or thietanyl-Ci-C 4 alkylene wherein the thietanyl moiety is substituted by one to five R 8 , oxo
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to three halogen atoms, C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Ci-C 4 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl, oxo-thietanyl, dioxo-thietanyl, d- C 8 alkylaminocarbonyl-methylene, d-C 8 haloalkylaminocarbonyl-methylene, d-
  • R 2 is d-C 6 alkyl or d-C 6 alkyl substituted by one to five R 6 , for example ethyl-, butyl-, but-2-yl-, 3-bromo-propyl-, 2,2,2-trifluoro-ethyl-, 3,3,3- trifluoro-propyl-, 2-methoxy-ethyl-, and 1 -methoxy-prop-2-yl-.
  • a group of preferred compounds are those wherein R 2 is C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one to five R 7 , for example cyclobutyl-, 2-fluoro-cyclopropyl and 2-methyl-cyclohex-1 - yl-.
  • R 2 is six to fourteen ring-membered aryl- d-dalkylene- or six to fourteen ring-membered aryl-d-dalkylene- wherein the six to fourteen ring- membered aryl moiety is substituted by one to five R 8 , for example phenyl-methyl-, 1 -phenyl-eth-1 -yl- , 2-phenyl-eth-1 -yl-, (3-chloro-phenyl)-methyl-, (2-fluoro-phenyl)-methyl-, (4-methoxy-phenyl)-methyl-, (2-trifluoromethyl-phenyl)-methyl-, and (2-trifluoromethoxy-phenyl)-methyl-.
  • R 2 is five to ten ring-membered heterocyclyl-Ci-C 2 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 2 alkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 , for example (pyrid-2-yl)- methyl-, (pyrid-3-yl)-methyl-, (2-chloro-pyrid-5-yl)-methyl-, (1-methyl-1 /-/-imidazol-4-yl)-methyl-, (furan-2-yl)-methyl-, 2-(thiophen-2'-yl)-eth-1-yl-, 2-(indol-3'-yl)-eth-1-yl-, (1 H-benzimidazol-2-yl)- methyl-, (oxetan-2-yl)-methyl-, (tetrahydrofuran-2
  • a group of preferred compounds are those wherein R 2 is five to ten ring-membered heterocyclyl-Ci-C 2 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 2 alkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 in which the five to ten ring- membered heterocyclyl group is selected from 1 ,2,3 triazolyl, 1 ,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo-
  • a group of preferred compounds are those wherein R 2 is six to ten ring-membered heteroaryl-Ci-C 2 alkylene- or six to ten ring-membered heteroaryl-Ci-C 2 alkylene- wherein the six to ten ring-membered heteroaryl moiety is substituted by one to five R 8 .
  • R 2 is six to fourteen ring-membered aryl or six to fourteen ring-membered aryl substituted by one to five R 8 , for example 2-chloro-phenyl-, 3- fluoro-phenyl-, 2-methyl-phenyl-, 2-chloro-6-methyl-phenyl-, 2-trifluoromethyl-phenyl-, and 2,4- dimethoxy-phenyk
  • R 2 is five to ten ring-membered heterocyclyl or five to ten ring-membered heterocyclyl substituted by one to five R 8 , for example 3- methyl-pyrid-2-yl-, 1 ,3-dimethyl-1 /-/-pyrazol-5-yl-, 4-methyl-thiazol-2-yl-, 5-methyl-thiadiazol-2-yl-, quinolin-2-yl-, quinolin-5-yl-, benzothiazol-6-yl-, 4-methyl-benzothiazol-2-yl-, thietan-3-yl-, 1-oxo- thietan-3-yl-, 1 , 1-dioxo-thietan-3-yl-, and 3-methyl-thietan-3-yl-, more preferably R 2 is oxetanyl, thietanyl, oxo-thietanyl or dioxo-thi
  • a group of preferred compounds are those wherein R 2 is five to ten ring-membered heterocyclyl- or five to ten ring-membered heterocyclyl substituted by one to five R 8 in which the five to ten ring-membered heterocyclyl group is selected from 1 ,2,3 triazolyl, 1 ,2,4 triazolyl, tetrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, tetrahydrothiophenyl, isoxazolinyl, pyridyl, tetrahydrofuranyl, imidazolyl, pyrazolyl, pyrrolyl, thiazolyl, oxetanyl, thietanyl, oxo-thietanyl and dioxo-thietanyl, preferably the five to ten ring-membered heterocyclyl group is selected from thietanyl, oxo-
  • R 2 is Ci-C 8 alkylaminocarbonyl-Ci-C 4 alkylene, Ci-C 8 haloalkylaminocarbonyl-Ci-C 4 alkylene, or C 3 -C 8 cycloalkyl-aminocarbonyl-Ci-C4 alkylene, more preferably Ci-C 4 alkylaminocarbonyl-Ci-C 4 alkylene, d-dhaloalkylaminocarbonyl-d- C 4 alkylene, or C 3 -C 6 cycloalkyl-aminocarbonyl-Ci-C 4 alkylene, most preferably d- C 4 alkylaminocarbonyl-Ci-C 2 alkylene or Ci-C 4 haloalkylaminocarbonyl-Ci-C 2 alkylene.
  • R 3 is chlorodifluoromethyl or trifluoromethyl, most preferably trifluoromethyl.
  • R 4 is six to fourteen ring-membered aryl or six to fourteen ring-membered aryl substituted by one to five R 9 , more preferably six to fourteen ring-membered aryl substituted by one to three R 9 , more preferably phenyl substituted by one to three R 9 , even more preferably 3,5- dibromo-phenyl-, 3,5-dichloro-phenyl-, 3,5-bis-(trifluoromethyl)-phenyl-, 3,4-dichloro-phenyl-, 3,4,5- trichloro-phenyl- 3-trifluoromethyl-phenyl-, 4-bromo-3,5-dichloro-phenyl or 3-chloro-5-trifluoromethyl- phenyl, most preferably R 4 is 3,5-dichloro-phenyl.
  • each R 5 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, d- C 8 alkenyl, Ci-C 8 haloalkenyl, Ci-C 8 alkoxy-, or Ci-C 8 haloalkoxy-, more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, methoxy, difluoromethoxy, or
  • each R 6 is independently halogen, cyano, nitro, hydroxy, Ci-C 8 alkoxy-, d- C 8 haloalkoxy-, d-dalkylcarbonyl-, d-dalkoxycarbonyl-, mercapto, d-dalkylthio-, d- dhaloalkylthio-, d-dalkylsulfinyl-, d-dhaloalkylsulfinyl-, d-dalkylsulfonyl-,
  • each R 6 is independently halogen, cyano, nitro, hydroxy, d-C 8 alkoxy-, d-dhaloalkoxy-, mercapto, d-C 8 alkylthio-, d-dhaloalkylthio-, more preferably bromo, chloro, fluoro, methoxy, or methylthio, most preferably chloro, fluoro, or methoxy.
  • each R 7 is independently halogen or d-C 8 alkyl, more preferably each R 7 is independently chloro, fluoro or methyl, most preferably fluoro or methyl.
  • each R 8 is independently halogen, cyano, nitro, d-C 8 alkyl, d-C 8 haloalkyl, C 2 - C 8 alkenyl, C 2 -C 8 naloalkenyl, C 2 -C 8 alkynyl, d-dhaloalkynyl, hydroxy, d-dalkoxy-, d-C 8 haloalkoxy- , mercapto, d-dalkylthio-, d-dhaloalkylthio-, d-C 8 alkylsulfinyl-, d-dhaloalkylsulfinyl-, d- dalkylsulfonyl-, d-dhaloalkylsulfonyl-, d-C 8 alkylcarbonyl-, d-dalkoxycarbonyl-, six to fourteen ring-membered aryl or six to fourteen ring-
  • each R 9 is independently halogen, d-C 8 alkyl, d-C 8 haloalkyl, d-C 8 alkoxy-, d- C 8 haloalkoxy-, d-dalkylthio-, or d-C 8 haloalkylthio-, more preferably bromo, chloro, fluoro, trifluoromethyl, methoxy, or methylthio, most preferably bromo or chloro.
  • each R 0 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably bromo, chloro, fluoro, nitro, or methyl, most preferably chloro, fluoro, or methyl.
  • each Z is independently halogen, cyano, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy, or Ci-C 4 haloalkoxy, more preferably each Z is independently hydrogen, halogen, methyl, halomethyl, methoxy or halomethoxy.
  • P is P1 ;
  • a 1 , A 2 , A 3 , A 4 and A 5 are independently of each other C-H, C-R 5 , or nitrogen and at least one of A 1 or A 5 is C-P;
  • G is oxygen or sulfur
  • R is hydrogen, Ci-C 8 alkyl, d-C 8 alkoxy-, Ci-C 8 alkylcarbonyl-, or Ci-C 8 alkoxycarbonyl-;
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one to five R 7 , six to fourteen ring-membered aryl-Ci-C 4 alkylene- or six to fourteen ring-membered aryl-Ci-C 4 alkylene- wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 , six to fourteen ring-membered aryl or six to fourteen ring- membered aryl substituted by one to five R 8 ,
  • R 3 is d-Cshaloalkyl
  • R 4 is six to fourteen ring-membered aryl or six to fourteen ring-membered aryl substituted by one to five R 9 , or six to ten ring-membered heteroaryl or six to ten ring-membered heteroaryl substituted by one to five R 9 ;
  • each R 5 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, Ci-C 8 alkenyl, d- C 8 haloalkenyl, d-dalkynyl, d-C 8 naloalkynyl, C 3 -d 0 cycloalkyl, d-C 8 alkoxy-, d-C 8 haloalkoxy-, d- C 8 alkylthio-, d-C 8 haloalkylthio-, d-C 8 alkylsulfinyl-, d-C 8 naloalkylsulfinyl-, d-C 8 alkylsulfonyl-, or d- C 8 haloalkylsulfonyl-;
  • each R 6 is independently halogen, cyano, nitro, hydroxy, d-dalkoxy-, d-dhaloalkoxy-, d- dalkylcarbonyl-, d-dalkoxycarbonyl-, mercapto, d-dalkylthio-, d-C 8 haloalkylthio-, d- dalkylsulfinyl-, d-dhaloalkylsulfinyl-, d-dalkylsulfonyl-,
  • each R 7 is independently halogen or d-C 8 alkyl
  • each R 8 and R 9 is independently halogen, cyano, nitro, d-C 8 alkyl, d-C 8 haloalkyl, d-dalkenyl, C 2 - dhaloalkenyl, d-dalkynyl, C 2 -C 8 naloalkynyl, hydroxy, d-dalkoxy-, d-dhaloalkoxy-, mercapto, d-C 8 alkylthio-, d-dhaloalkylthio-, d-dalkylsulfinyl-, d-dhaloalkylsulfinyl-, d-dalkylsulfonyl-, d-C 8 naloalkylsulfonyl-, d-dalkylcarbonyl-, d-dalkoxycarbonyl-, six to fourteen ring-membered aryl or six to fourteen ring-membered
  • each R 0 is independently halogen, cyano, nitro, Ci-C 4 alkyl, Ci-C 4 haloalkyl, d-C 4 alkoxy-, or d-
  • a group of preferred compounds are those wherein
  • a 1 , A 2 , A 3 , A 4 and A 5 are independently of each other C-H, C-R 5 , or nitrogen and at least one of A 1 P is P1 ;
  • a 1 , A 2 , A 3 , A 4 and A 5 are independently of each other C-H, C-R 5 , or nitrogen and at least one of A 1 is C-P;
  • G is oxygen
  • Y is CH 2 ;
  • R is hydrogen
  • R 2 is C 2 -C 6 alkyl or C 2 -C 6 alkyl substituted by one to three halogen atoms, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-Ci-C 2 alkylene- or phenyl-Ci-C 2 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 2 alkylene- or pyridyl-Ci-C 2 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl, oxo-thietanyl, dioxo-thietanyl, Ci-C 4 alkylaminocarbonyl-Ci-C 2 alkylene or Ci-C 4 haloalkylaminocarbonyl-Ci-C 2 al
  • R 3 is trifluoromethyl
  • R 4 is 3,5-dichloro-phenyl
  • R 5 is methyl
  • each R 8 is independently bromo, chloro, fluoro, cyano or methyl
  • G is oxygen
  • Y is CH 2 ;
  • R is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl-;
  • R 2 is Ci-C 8 alkyl or d-C 8 alkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 - C-iocycloalkyl substituted by one to five R 7 , six to fourteen ring-membered aryl-Ci-C 4 alkylene- or six to fourteen ring-membered aryl-Ci-C 4 alkylene- wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- or five to ten ring-membered heterocyclyl-Ci-C 4 alkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 , six to fourteen ring-membered aryl or six to fourteen ring- membered aryl substituted by one to five R 8 ,
  • X 1 and X 2 are indenpendently H, halogen, Ci-C 3 alkyl, Ci-C 3 haloalkyl; R 3 is d-C 8 haloalkyl;
  • R 4 is phenyl substituted by one to three R 9 ;
  • R 5 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, Ci-C 8 alkenyl, d- C 8 haloalkenyl, d-C 8 alkoxy-, or Ci-C 8 haloalkoxy-;
  • each R 6 is independently halogen, cyano, nitro, hydroxy, Ci-C 8 alkoxy-, Ci-C 8 haloalkoxy-, mercapto, Ci-C 8 alkylthio-, Ci-C 8 haloalkylthio-;
  • each R 7 is independently chloro, fluoro or methyl
  • each R 8 is independently halogen, cyano, nitro, Ci-C 8 alkyl, Ci-C 8 haloalkyl, Ci-C 8 alkoxy-, d- C 8 haloalkoxy-;
  • each R 9 is independently halogen, Ci-C 8 alkyl, Ci-C 8 haloalkyl, Ci-C 8 alkoxy-, d-
  • Ci-C 8 alkylthio- Ci-C 8 haloalkylthio-
  • a 1 , A 2 , A 3 , A 4 and A 5 are independently of each other C-H, C-R 5 , or nitrogen and at least one of A 1 G is oxygen;
  • Y is CH 2 ;
  • R is hydrogen, methyl or ethyl
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to five R 6 , C 3 -Ci 0 cycloalkyl or C 3 - docycloalkyl substituted by one to five R 7 , phenyl-d-dalkylene- or phenyl-d-dalkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-d-dalkylene- or pyridyl-d-dalkylene- wherein the pyridyl moiety is substituted by one to four R 8 , oxetanyl or oxetanyl substituted by one to five R 8 , thietanyl-d-d alkylene or thietanyl-d-d alkylene wherein the thietanyl moiety is substituted by one to five R 8 , oxo-thietanyl-d-d alkylene or ox
  • X 1 and X 2 are independently H, d-C 3 alkyl
  • R 3 is chlorodifluoromethyl or trifluoromethyl
  • R 4 is 3,5-dibromo-phenyl-, 3,5-dichloro-phenyl-, 3,5-bis-(trifluoromethyl)-phenyl-, 3,4- dichloro-phenyl-, 3,4,5-trichloro-phenyl-, 3-trifluoromethyl-phenyl-, 4-bromo-3,5-dichloro-phenyl or 3- chloro-5-trifluoromethyl-phenyl;
  • R 5 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, vinyl, methoxy, difluoromethoxy, or trifluoromethoxy;
  • each R 6 is independently bromo, chloro, fluoro, methoxy, or methylthio
  • each R 7 is independently fluoro or methyl
  • each R 8 is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy;
  • a further group of preferred compounds are those wherein
  • a , A 2 , A 3 , A 4 and A 5 are independently of each other C-H, C-R 5 , or nitrogen and at least one of A 1 is C-P;
  • G is oxygen
  • Y is CH 2 ;
  • R is hydrogen
  • R 2 is Ci-C 8 alkyl or Ci-C 8 alkyl substituted by one to three halogen atoms, C 3 -Ci 0 cycloalkyl or C 3 -Ci 0 cycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-Ci-C 4 alkylene- or phenyl-Ci-C 4 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 4 alkylene- or pyridyl-Ci-C 4 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl, oxo-thietanyl, dioxo-thietanyl, Ci-C 4 alkylaminocarbonyl-Ci-C 4 alkylene, d- C 4 haloalkylaminocarbonyl-Ci-C 4
  • X 1 and X 2 are hydrogen
  • R 3 is trifluoromethyl
  • R 4 is 3,5-dichloro-phenyl
  • R 5 is methyl
  • each R 8 is independently bromo, chloro, fluoro, cyano or methyl
  • P is P1 ;
  • a 1 , A 2 , A 3 , A 4 and A 5 are independently of each other C-H, C-R 5 , or nitrogen and at least one of A 1 is C-P;
  • G is oxygen
  • Y is CH 2 ;
  • R is hydrogen
  • R 2 is C 2 -C 6 alkyl or C 2 -C 6 alkyl substituted by one to three halogen atoms, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkyl substituted by one or two groups independently selected from fluoro and methyl, phenyl-Ci-C 2 alkylene- or phenyl-Ci-C 2 alkylene- wherein the phenyl moiety is substituted by one to five R 8 , pyridyl-Ci-C 2 alkylene- or pyridyl-Ci-C 2 alkylene- wherein the pyridyl moiety is substituted by one to four R 8 , thietanyl, oxo-thietanyl, dioxo-thietanyl, Ci-C 4 alkylaminocarbonyl-Ci-C 2 alkylene or Ci-C 4 haloalkylaminocarbonyl-Ci-C 2 al
  • X 1 and X 2 are H;
  • R 3 is trifluoromethyl
  • R 4 is 3,5-dichloro-phenyl
  • R 5 is methyl
  • each R 8 is independently bromo, chloro, fluoro, cyano or methyl
  • the present invention provides compounds of formula (la) wherein P signifies P1 and P1 , G, X 1 , X 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I); or a salt or A/-oxide thereof.
  • P signifies P1 and P1
  • G, X 1 , X 2 , R 3 , R 4 and R 5 are as defined for compounds of formula (I); or a salt or A/-oxide thereof.
  • the preferences for G, R , R 2 , R 3 , R 4 and R 5 are the same as the preferences set out for the corresponding substituents of compounds of the formula (I).
  • the present invention provides compounds of formula (lb)
  • R x is hydrogen or d-C 4 alkoxy
  • R 2x is hydrogen, halogen, N0 2 , NHCOCF 3 , NHCO-cPr, NH 2 , NHCOCH 2 CH 3 , NHCOCH 2 CF 3 , [(4- cyano-2-methyl-benzoyl)amino], [bis(cyclopropanecarbonyl)amino], [(2-methoxyacetyl)amino], [(4- cyanobenzoyl)amino], NHCO-cBu, [(2-ethoxyacetyl)amino], [(2-chlorobenzoyl)amino], (pyridine-4- carbonylamino), [(4-fluorobenzoyl)amino], [(H 4-fluoro-2-methyl-benzoyl)amino], [(2- fluorobenzoyl)amino], (3-methoxypropanoylamino), (pyridine-3-carbonylamino), [(2,4- dimethylbenzoyl)
  • R 3x is hydrogen, Me, Br, CN, F, N0 2 , NH 2 , NHCOCF 3 , NHCOcPr, COOH, CONHCH 2 CF 3 , CONHcBu,
  • R 4x is hydrogen
  • R 5x is hydrogen or halogen
  • R 6x is hydrogen or halogen
  • R 7x is hydrogen or halogen
  • R 8x is hydrogen or halogen
  • the present invention provides compounds of formula (lb')
  • X 1 , X 2 , R 3 , R 4 , A 1 , A 2 , A 3 , and A 4 are as defined for a compound of formula (I) andf A 1 and/or A 5 are C-R, R is amino, nitro, azido, hydroxyl, halo such as fluoro, chloro, bromo or iodo. Preferably R is amino, nitro or azido
  • a further group of novel intermediates are compounds of formula IV and V
  • P A , P B and P c independently are selected from d-dalkyl or d-dalkyl substituted by one to five R 6 , C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkyl substituted by one to five R 7 , six to fourteen ring- membered aryl-CrC 4 alkylene- or six to fourteen ring-membered aryl-Ci-C 4 alkylene- wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-C-i-C 4 alkylene- or five to ten ring-membered heterocyclyl-CrC 4 alkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 , six to fourteen ring- membered aryl or six to fourteen ring-membered aryl substituted by
  • P A , P B and P c are six to fourteen ring-membered aryl or six to fourteen ring-membered aryl substituted by one to five R 8 , more preferably phenyl or phenyl substituted by one to five R 8
  • the preferences for R 3 and R 4 are the same as the preferences set of for the corresponding substituents of a compound of formula (I).
  • a preferred group of compounds of formula VI are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • G is oxygen
  • X 2 is hydrogen, alkoxy of halogen more preferably hydrogen.
  • P A , P B and P c independently are selected from d-dalkyl or d-dalkyl substituted by one to five R 6 , C 3 -docycloalkyl or C 3 -d 0 cycloalkyl substituted by one to five R 7 , six to fourteen ring- membered aryl-d-C 4 alkylene- or six to fourteen ring-membered aryl-d-dalkylene- wherein the six to fourteen ring-membered aryl moiety is substituted by one to five R 8 , five to ten ring-membered heterocyclyl-d-C 4 alkylene- or five to ten ring-membered heterocyclyl-d-dalkylene- wherein the five to ten ring-membered heterocyclyl moiety is substituted by one to five R 8 , six to fourteen ring- membered aryl or six to fourteen ring-membered aryl substituted by one to five R 8 ,
  • P A , P B and P c are six to fourteen ring-membered aryl or six to fourteen ring-membered aryl substituted by one to five R 8 , more preferably phenyl or phenyl substituted by one to five R 8
  • the preferences for R 3 and R 4 are the same as the preferences set of for the corresponding substituents of a compound of formula (I).
  • a preferred group of compounds of formula VI are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • G is oxygen
  • X 2 is hydrogen, alkoxy of halogen more preferably hydrogen.
  • R 3 and R 4 are as defined for the compounds of formula I, or a salt or N-oxide thereof.
  • the preferences for R 3 and R 4 are the same as the preferences set of for the corresponding substituents of a compound of formula (I).
  • a preferred group of compounds of formula VIII are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • X2 and G are as defined for compounds of formula VI.
  • R 3 and R 4 are as defined for compounds of formula I, and X is a tin derivative, e.g. Sn(R 3 ) 3 wherein each R 3 is independently Ci-C 6 alkyl, a boron derivative, e.g. BF 3 , B(OH) 2 or B(OR) 2 , wherein each R is independnetly Ci-C 6 -alkyl, Ci-C 6 -cycloalkyl or optionally substituted Ci-C 6 - cycloalkyl, e.g.
  • Ci-C 4 alkyl or Ci-C 4 haloalkyl optionally substituted by halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl, a Ci-C 4 alkenyl group which is substituted by halogen, C 1 -C4 alkyl or Ci-C 4 haloalkyl or unsubstituted, a leaving group, such as halogen, d-C 8 alkoxy, Ci-C 8 alkylsulfonyloxy, Ci-C 8 haloalkylsulfonyloxy, Ci-C 8 arylsulfonyloxy, optionally substituted Ci-C 8 arylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g.
  • X B is -N 2 + CI " , -N 2 + BF 4 " , -N 2 + Br " , -N 2 + PF 6 _) , phosphonate esters (e.g. -OP(0)(OR) 2, wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride, or C(0)R wherein R is halogen, OH or C-rC 15 alkoxy or a salt or N-oxide thereof.
  • a preferred group of compounds of formula IX are those wherein R 3 is CF 3 and R 4 is phenyl substituted by 1 to 5 R 9 .
  • Table 1 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2H, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 2 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2H, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 3 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2H, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 4 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2H, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 5 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 6 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 7 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 8 provides 672 compounds of formula lA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 9 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 10 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 11 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 12 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 13 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CH2CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 14 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CH2CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 15 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CH2CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 16 provides 672 compounds of formula lA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CH2CF3, R4 is 3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 17 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2H, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 18 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2H, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 19 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2H, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 20 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2H, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 21 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 22 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 23 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 24 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 25 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 26 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 27 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 28 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 29 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CH2CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 30 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CH2CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 31 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CH2CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 32 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CH2CF3, R4 is 3,5-dichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 33 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2H, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 34 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2H, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 35 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2H, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 36 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2H, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 37 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 38 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 39 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 40 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 41 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 42 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 43 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 44 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 45 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CH2CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 46 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CH2CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 47 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CH2CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 48 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CH2CF3, R4 is 3,4,5-trifuorophenyl and R2x and R3x are as defined in Table P1.
  • Table 49
  • Table 49 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2H, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 50 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2H, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 51 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2H, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 52 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2H, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 53 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 54 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 55 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 56 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 57 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 58 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 59 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 60 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 61 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CH2CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 62 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CH2CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 63 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CH2CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 64 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CH2CF3, R4 is 3,4,5-trichlorophenyl and R2x and R3x are as defined in Table P1.
  • Table 65 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2H, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 66 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2H, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 67 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2H, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 68 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2H, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 69 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 70 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 71 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 72 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 73 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 74 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 75 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 76 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 77 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CH2CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 78 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CH2CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 79 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CH2CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 80 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CH2CF3, R4 is 4-chloro-3,5-difluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 81 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2H, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 82 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2H, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 83 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2H, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 84 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2H, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 85
  • Table 85 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 86 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 87 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 88 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 89 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 90 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 91 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 92 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 93 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CH2CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 94 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CH2CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 95 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CH2CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 96 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CH2CF3, R4 is 3,5-dichloro-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 97 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2H, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 98 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2H, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 99 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2H, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 100 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2H, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 101 provides 672 compounds of formula lA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 102 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 103 provides 672 compounds of formula lA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 104 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 105 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CF2CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 106 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CF2CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 107 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CF2CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 108 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CF2CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 109 provides 672 compounds of formula lA and 672 compounds of formula IB wherein X1 is H, X2 is H, R3 is CH2CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 1 10 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is H, R3 is CH2CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 1 1 1 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is H, X2 is CH3, R3 is CH2CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • Table 1 12 provides 672 compounds of formula IA and 672 compounds of formula IB wherein X1 is CH3, X2 is CH3, R3 is CH2CF3, R4 is 3,5-ditrifluoromethyl-4-fluorophenyl and R2x and R3x are as defined in Table P1.
  • the compounds of the invention may be made by a variety of methods as shown in the following Schemes.
  • the compound 4 can then be converted to compound 5 by treating it with a suitable nucleophile (LAH, NaBH4, organometallic species such as alkylmagnesium halides) followed by treatment with halogenating agent such as (SOX 2 , PX 5 ).
  • LAH nucleophile
  • NaBH4 organometallic species such as alkylmagnesium halides
  • halogenating agent such as (SOX 2 , PX 5
  • the alkyl halide species 5 can then be transformed into its Wittig salt (6) by treatment with the suitable phosphorus reagent (PR 6 R 7 R 8 ).
  • Compound of type 6 can then be condensed with the carbonyl compounds of type 7 to obtained the olefin 8. Reduction of the compound 8 can then give rise to the amine derivative which in turn be functinalized further (alkylation, acylation) to produce compound of type IA.
  • Compound of formula (8) can also be prepared alternatively by treating the carbonyl derivative (4) with the Wittig salt of type 9. Compound 8 can then be converted to compound of type 1 A following steps as described in scheme 1.
  • Compound of formula 1A can alsobe prepared via Heck coupling reaction between compound of type 10 and styrene derivative of type 1 1 .
  • the compound 1 1 can be easily prepared either from compound 12 by Wittig reaction or from compound 13 via Palladium catalysed coupling reaction between suitable aryl and olefinic partner.
  • Preparation of compound 10 can be done starting with the a,b unsaturated carbonyl derivative of type 14 which on treatment with hydroxylamine and a suitable base can give rise to acylhydroxylamine derivative of type 15, which will then undergo intramolecular cyclization via Michael Addition to give compound 16.
  • Compound 16 can then be easily converted to compound 10 by treating it with various halogenating agent such as (SOX 2 , PX 5 ).
  • 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.
  • pest species which may be controlled by the compounds of formula (I) include: 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. thrips
  • Leptinotarsa decemlineata Coldiella occidentalis
  • Thrips spp. thrips
  • Leptinotarsa decemlineata Coldiella occidentalis
  • Thrips spp. thrips
  • Leptinotarsa decemlineata Coldiella occidentalis
  • Thrips spp. thrips
  • Leptinotarsa decemlineata Coldiella occidentalis
  • Anthonomus grandis boll weevil
  • Linognathus spp. bits 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
  • Trichostrongylus spp. gastro intestinal nematodes
  • Deroceras reticulatum slug
  • the invention therefore provides a method of 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 or acarines.
  • plant 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
  • An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is
  • Clearfield® summer rape canola
  • 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 LibertyLink®.
  • Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).
  • Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds).
  • Examples of transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®.
  • Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding ("stacked" transgenic events).
  • seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.
  • Crops are also to be understood as being those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavor).
  • output traits e.g. improved storage stability, higher nutritional value and improved flavor.
  • 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 to10kg per hectare, preferably from 1 g to 6kg per hectare, more preferably from 1 g to 1 kg per hectare.
  • a compound of formula (I) When used in a seed dressing, a compound of formula (I) is used at a rate of 0.0001 g to 10g (for example 0.001 g or 0.05g), preferably 0.005g to 10g, more preferably 0.005g to 4g, per kilogram of seed.
  • the present invention provides an insecticidal, acaricidal, nematicidal or molluscicidal composition
  • an insecticidal, acaricidal, nematicidal or 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 or acaricidal 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 (DP) may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina,
  • 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.
  • 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 dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).
  • water-soluble inorganic salts such as sodium bicarbonate, sodium carbonate or magnesium sulfate
  • water-soluble organic solids such as a polysaccharide
  • 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).
  • organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 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),
  • A/-alkylpyrrolidones such as /V-methylpyrrolidone or A/-octylpyrrolidone
  • dimethyl amides of fatty acids such as C 8 -Ci 0 fatty acid dimethylamide
  • chlorinated hydrocarbons such as C 8 -Ci 0 fatty acid dimethylamide
  • Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at ambient 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 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 n-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-; ' sopropyl- and tri-; ' sopropyl-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
  • 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); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
  • 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, nonyl
  • Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).
  • hydrophilic colloids such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose
  • 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 locus of the pests such as a habitat of the pests, or a growing plant liable to infestation by the pests
  • 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 land or aerial irrigation systems.
  • 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, fungicide, synergist, herbicide 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), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin or
  • Carbamates including aryl carbamates
  • pirimicarb triazamate
  • cloethocarb carbofuran
  • furathiocarb furathiocarb
  • ethiofencarb aldicarb
  • thiofurox carbosulfan
  • bendiocarb fenobucarb
  • propoxur methomyl or oxamyl
  • Benzoyl ureas such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron or chlorfluazuron;
  • Organic tin compounds such as cyhexatin, fenbutatin oxide or azocyclotin;
  • Macrolides such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad , azadirachtin or spinetoram;
  • Organochlorine compounds such as endosulfan (in particular alpha-endosulfan), benzene hexachloride, DDT, chlordane or dieldrin;
  • 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, nithiazine or flonicamid;
  • Diacylhydrazines such as tebufenozide, chromafenozide or methoxyfenozide
  • Diphenyl ethers such as diofenolan or pyriproxifen
  • Diamides such as flubendiamide, chlorantraniliprole or cyantraniliprole;
  • pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition.
  • selective insecticides for particular crops for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed.
  • insecticides or acaricides specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as
  • fungicidal compounds which may be included in the composition of the invention are (E)-A/-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide (SSF-129), 4-bromo-2-cyano-A/,A/-dimethyl-6-trifluoromethylbenzimidazole-1 -sulfonamide, a-[A/-(3-chloro-2,6-
  • timibenconazole tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, zineb, ziram ; 1 ,3-Dimethyl-1 H-pyrazole-4-carboxylic acid (4'-methylsulfanyl- biphenyl-2-yl)-amide, 1 ,3-Dimethyl-1 H-pyrazole-4-carboxylic acid (2-dichloromethylene-3-ethyl-1 - methyl-indan-4-yl)-amide, and 1 ,3-Dimethyl-4H-pyrazole-4-carboxylic acid [2-(2,4-dichloro-phenyl)-2- methoxy-1 -methyl-e
  • the compounds of formula (I) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
  • synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.
  • Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.
  • An example of a rice selective herbicide which may be included is propanil.
  • An example of a plant growth regulator for use in cotton is PIXTM.
  • Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type.
  • other formulation types may be prepared.
  • one active ingredient is a water insoluble solid and the other a water insoluble liquid
  • the resultant composition is a suspoemulsion (SE) formulation.
  • the compounds of the invention are also useful in the field of animal health, e.g. they may be used against parasitic invertebrate pests, more preferably against parasitic invertebrate pests in or on an animal.
  • pests include nematodes, trematodes, cestodes, flies, mites, tricks, lice, fleas, true bugs and maggots.
  • the animal may be a non-human animal, e.g. an animal associated with agriculture, e.g. a cow, a pig, a sheep, a goat, a horse, or a donkey, or a companion animal, e.g . a dog or a cat.
  • the invention provides a compound of the invention for use in a method of therapeutic treatment.
  • the invention in a further aspect relates to a method of controlling parasitic invertebrate pests in or on an animal comprising administering a pesticidally effective amount of a compound of the invention.
  • the administration may be for example oral administration, parenteral administration or external administration, e.g. to the surface of the animal body.
  • the invention relates to a compound of the invention for controlling parasitic invertebrate pests in or on an animal.
  • the invention relates to use of a compound of the invention in the manufacture of a medicament for controlling parasitic invertebrate pests in or on an animal
  • the invention relates to a method of controlling parasitic invertebrate pests comprising administering a pesticidally effective amount of a compound of the invention to the environment in which an animal resides.
  • the invention relates to a method of protecting an animal from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention.
  • the invention relates to a compound of the invention for use in protecting an animal from a parasitic invertebrate pest.
  • the invention relates to use of a compound of the invention in the manufacture of a medicament for protecting an animal from a parasitic invertebrate pest.
  • the invention provides a method of treating an animal suffering from a parasitic invertebrate pest comprising administering to the animal a pesticidally effective amount of a compound of the invention.
  • the invention relates to a compound of the invention for use in treating an animal suffering from a parasitic invertebrate pest.
  • the invention relates to use of a compound of the invention in the manufacture of a medicament for treating an animal suffering from a parasitic invertebrate pest.
  • the invention provides a pharmaceutical composition
  • a pharmaceutical composition comprising a compound of the invention and a pharmaceutically suitable excipient.
  • the compounds of the invention may be used alone or in combination with one or more other biologically active ingredients.
  • the invention provides a combination product comprising a pesticidally effective amount of a component A and a pesticidally effective amount of component B wherein component A is a compound of the invention and component B is a compound as described below.
  • the compounds of the invention may be used in combination with anthelmintic agents.
  • anthelmintic agents include, compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in EP- 357460, EP-444964 and EP-594291.
  • Additional anthelmintic agents include semisynthetic and biosynthetic
  • avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO- 9522552.
  • Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole,
  • Additional anthelmintic agents include
  • imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel.
  • Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.
  • the compounds of the invention may be used in combination with derivatives and analogues of the paraherquamide/marcfortine class of anthelmintic agents, as well as the antiparasitic oxazolines such as those disclosed in US-5478855, US- 4639771 and DE-19520936.
  • the compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO-9615121 and also with anthelmintic active cyclic depsipeptides such as those described in WO-961 1945, WO-9319053, WO- 9325543, EP-626375, EP-382173, WO-9419334, EP-382173, and EP-503538.
  • the compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron;
  • ectoparasiticides for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron;
  • ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
  • the compounds of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers W095/19363 or WO04/72086, particularly the compounds disclosed therein.
  • Organophosphates acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, me
  • Carbamates alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801 , isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.
  • Pyrethroids acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E) - (1 R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta - cyfluthrin, cyfluthrin, a-cypermethrin, beta -cypermethrin, bioallethrin, bioallethrin((S)- cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, f
  • Arthropod growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.
  • antiparasitics acequinocyl, amitraz, AKD-1022, ANS-1 18, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI- 800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydra
  • Fungicides acibenzolar, aldimorph, ampropylfos, andoprim, azaconazole, azoxystrobin, benalaxyl, benomyl, bialaphos, blasticidin-S, Bordeaux mixture, bromuconazole, bupirimate, carpropamid, captafol, captan, carbendazim, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, copper oxychloride, copper salts, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, cyprofuram, RH-7281 , diclocymet, diclobutrazole, diclomezine, dicloran, difenoconazole, RP-407213, dimethomorph, domoxystrobin, diniconazole, diniconazole-M, dod
  • metominostrobin/fenominostrobin metrafenone, myclobutanil, neo-asozin, nicobifen, orysastrobin, oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propioconazole, proquinazid, prothioconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetrconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin, vinclozin.
  • Biological agents Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.
  • Bactericides chlortetracycline, oxytetracycline, streptomycin.
  • the compounds of the invention are preferably used in combination with imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin, benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, tridabendazole
  • a combination product of the invention may comprise a pesticidally effective amount of a compound of formula I and pesticidally effective amount of at least one additional parasitic invertebrate pest control active ingredient having a similar spectrum of control but a different site of action.
  • salts of chemical compounds are in equilibrium with their corresponding non salt forms, salts share the biological utility of the non salt forms.
  • salts of compounds of the invention may be useful for control of invertebrate pests and animal parasites.
  • Salts include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • the compounds of the invention also include N-oxides. Accordingly, the invention comprises combinations of compounds of the invention including N-oxides and salts thereof and an additional active ingredient including N-oxides and salts thereof.
  • compositions for use in animal health may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants).
  • formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such
  • Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
  • formulation auxiliaries and additives include those listed in McCutcheon 's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
  • the compounds of the invention can be applied without other adjuvants, but most often application will be of a formulation comprising one or more active ingredients with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use.
  • One method of application involves spraying a water dispersion or refined oil solution of the combination products.
  • Compositions with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.
  • Such sprays can be applied from spray containers such as a can, a bottle or other container, either by means of a pump or by releasing it from a pressurized container, e.g.
  • a pressurized aerosol spray can take various forms, for example, sprays, mists, foams, fumes or fog. Such spray compositions thus can further comprise propellants, foaming agents, etc. as the case may be.
  • a spray composition comprising a pesticidally effective amount of a compound of the invention and a carrier.
  • a spray composition comprises a pesticidally effective amount of a compound of the invention and a propellant.
  • propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ether, and mixtures of the foregoing.
  • a spray composition (and a method utilizing such a spray composition dispensed from a spray container) used to control at least one parasitic invertebrate pest selected from the group consisting of mosquitoes, black flies, stable flies, deer flies, horse flies, wasps, yellow jackets, hornets, ticks, spiders, ants, gnats, and the like, including individually or in combinations.
  • compositions comprising compounds according to the invention can be broadened considerably, and adapted to prevailing circumstances, by including other active substances.
  • the active substances can be of chemical or biological in type, and in the case of biological could be further modified from the biological species derived in nature.
  • Active substances include substances that control, repel or attract pests that damage or harm useful plants in general, but also substances that improve the growth of a useful plant, such as plant growth regulators, and substances that improve the performance of the active substance, such as synergists. Examples are insecticides, acaricides, nematicides, molluscicides, aligicides, virusicides, rodenticide, bactericides, fungicides, chemosterilants, anthelmintics. Examples of a biological active substance include baculovirus, plant extract, and bacteria.
  • mixtures of the compounds of formula I with other active substances may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity. For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled in their different development stages, or better behaviour relating to production, for example grinding or mixing, storage or use.
  • Individual active substances can occur in more than one group or class, and at more than one place within a group or class: information about the active substances, their spectrum, sources and classifications can be found from Compendium of Pesticide Common Names (see
  • compositions comprising an adjuvant include I + compounds selected from the group of substances consisting of petroleum oils;
  • Compositions comprising an acaricide include I + 1 , 1 -bis(4-chlorophenyl)-2-ethoxyethanol, I + 2,4-dichlorophenyl benzenesulfonate, I + 2-fluoro-A/-methyl-A/-1 -naphthylacetamide, I + 4- chlorophenyl phenyl sulfone, I + abamectin, I + acequinocyl, I + acetoprole, I + acrinathrin, I + aldicarb, I + aldoxycarb, I + alpha-cypermethrin, I + amidithion, I + amidoflumet, I + amidothioate, I + amiton, I + amiton hydrogen oxalate, I + amitraz, I + aramite, I + arsenous
  • chlorfenvinphos I + chlorobenzilate, I + chloromebuform, I + chloromethiuron, I + chloropropylate, I + chlorpyrifos, I + chlorpyrifos-methyl, I + chlorthiophos, I + cinerin I, I + cinerin II , I + cinerins, I + clofentezine, I + closantel, I + coumaphos, I + crotamiton, I + crotoxyphos, I + cufraneb, I + cyanthoate, I + cyflumetofen, I + cyhalothrin, I + cyhexatin, I + cypermethrin, I + DCPM, I + DDT, I + demephion, I + demephion-O, I + demephion-S, I + demeton, I + demeton-methyl, I + demeton-O, I + demeton-O-methyl, I + de
  • compositions comprising an anthelmintic include I + abamectin, I + crufomate, I + doramectin, I + emamectin, I + emamectin benzoate, I + eprinomectin, I + ivermectin, I + milbemycin oxime, I + moxidectin, I + piperazine, I + selamectin, I + spinosad and I + thiophanate;
  • compositions comprising an avicide include I + chloralose, I + endrin, I + fenthion, I + pyridin- 4-amine and I + strychnine;
  • Compositions comprising a biological control agent include I + Adoxophyes orana GV, I + Agrobacterium radiobacter, I + Amblyseius spp. , I + Anagrapha falcifera NPV, I + Anagrus atomus, I + Aphelinus abdominalis, I + Aphidius colemani, I + Aphidoletes aphidimyza, I + Autographa californica NPV, I + Bacillus firmus, I + Bacillus sphaericus Neide, I + Bacillus thuringiensis Berliner, I + Bacillus thuringiensis subsp. aizawai, I + Bacillus thuringiensis subsp.
  • Macrolophus caliginosus I + Mamestra brassicae NPV, I + Metaphycus helvolus, I + Metarhizium anisopliae var. acridum, I + Metarhizium anisopliae var. anisopliae, I + Neodiprion sertifer NPV and N. lecontei NPV, I + Orius spp. , I + Paecilomyces fumosoroseus, I + Phytoseiulus persimilis, I +
  • compositions comprising a soil sterilant include I + iodomethane and methyl bromide;
  • compositions comprising a chemosterilant include I + apholate, I + bisazir, I + busulfan, I + diflubenzuron, I + dimatif, I + hemel, I + hempa, I + metepa, I + methiotepa, I + methyl apholate, I + morzid, I + penfluron, I + tepa, I + thiohempa, I + thiotepa, I + tretamine and I + uredepa;
  • compositions comprising an insect pheromone include I + (E)-dec-5-en-1 -yl acetate with (E)- dec-5-en-1 -ol, I + (E)-tridec-4-en-1 -yl acetate, I + (E)-6-methylhept-2-en-4-ol, I + (EZ)-tetradeca- 4, 10-dien-1 -yl acetate, I + (Z)-dodec-7-en-1 -yl acetate, I + (Z)-hexadec-l 1 -enal, I + (Z)-hexadec-l 1 - en-1 -yl acetate, I + (Z)-hexadec-13-en-1 1 -yn-1 -yl acetate, I + (Z)-icos-13-en-10-one, I + (Z)-tetradec- 7-en-1 -al, I + (Z)-tetradec-9-en
  • compositions comprising an insect repellent include I + 2-(octylthio)ethanol, I +
  • compositions comprising an insecticide include I + 1 -dichloro-1 -nitroethane, I + 1 , 1 -dichloro- 2,2-bis(4-ethylphenyl)ethane , I +, I + 1 ,2-dichloropropane, I + 1 ,2-dichloropropane with 1 ,3- dichloropropene, I + 1 -bromo-2-chloroethane, I + 2,2,2-trichloro-1 -(3,4-dichlorophenyl)ethyl acetate, I + 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, I + 2-(1 ,3-dithiolan-2-yl)phenyl
  • brofenvalerate I + bromfenvinfos, I + bromocyclen, I + bromo-DDT, I + bromophos, I + bromophos- ethyl, I + bufencarb, I + buprofezin, I + butacarb, I + butathiofos, I + butocarboxim, I + butonate, I + butoxycarboxim, I + butylpyridaben, I + cadusafos, I + calcium arsenate, I + calcium cyanide, I + calcium polysulfide, I + camphechlor, I + carbanolate, I + carbaryl, I + carbofuran, I + carbon disulfide, I + carbon tetrachloride, I + carbophenothion, I + carbosulfan, I + cartap, I + cartap hydrochloride, I + vertex, I + chlorbicyclen, I + chlordane, I + chloride
  • cyanofenphos I + cyanophos, I + cyanthoate, I + cyclethrin, I + cycloprothrin, I + cyfluthrin, I + cyhalothrin, I + cypermethrin, I + cyphenothrin, I + cyromazine, I + cythioate, I + cf-limonene, I + d- tetramethrin, I + DAEP, I + dazomet, I + DDT, I + decarbofuran, I + deltamethrin, I + demephion, I + demephion-O, I + demephion-S, I + demeton, I + demeton-methyl, I + demeton-O, I + demeton-O- methyl, I + demeton-S, I + demeton-S-methyl, I + demeton-S-methylsulphon, I + dia
  • Compositions comprising a molluscicide include I + bis(tributyltin) oxide, I + bromoacetamide, I + calcium arsenate, I + cloethocarb, I + copper acetoarsenite, I + copper sulfate, I + fentin, I + ferric phosphate, I + metaldehyde, I + methiocarb, I + niclosamide, I + niclosamide-olamine, I +
  • compositions comprising a nematicide include 1+ AKD-3088, I + 1 ,2-dibromo-3- chloropropane, I + 1 ,2-dichloropropane, I + 1 ,2-dichloropropane with 1 ,3-dichloropropene, 1 + 1 ,3- dichloropropene, I + 3,4-dichlorotetrahydrothiophene 1 , 1 -dioxide, I + 3-(4-chlorophenyl)-5- methylrhodanine, I + 5-methyl-6-thioxo-1 ,3,
  • compositions comprising a synergist include I + 2-(2-butoxyethoxy)ethyl piperonylate, I + 5- (1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, I + farnesol with nerolidol, I + MB-599, I + MGK 264, I + piperonyl butoxide, I + piprotal, I + propyl isomer, I + S421 , I + sesamex, I + sesasmolin and I + sulfoxide;
  • compositions comprising an animal repellent include l+ anthraquinone, I + chloralose, I + copper naphthenate, I + copper oxychloride, I + diazinon, I + dicyclopentadiene, I + guazatine, I + guazatine acetates, I + methiocarb, I + pyridin-4-amine, I + thiram, I + trimethacarb, I + zinc naphthenate and I + ziram;
  • compositions include I + Brofluthrinate, I + Cycloxaprid, I + Diflovidazine, I +
  • Composition also include mixtures of compound of formula I and an active substance referenced by a code, such as I + code AE 1887196 (BSC-BX60309), I + code NNI-0745 GR, I + code IKI-3106, I + code JT-L001 , I + code ZNQ-08056, I + code IPPA152201 , I + code HNPC-A9908 (CAS: [66041 1 -21 -2]), I + code HNPC-A2005 (CAS: [860028-12-2]), I + code JS1 18, I + code ZJ0967, I + code ZJ2242, I + code JS71 19 (CAS: [929545-74-4]), I + code SN-1 172, I + code HNPC- A9835, I + code HNPC-A9955, I + code HNPC-A3061 , I + code Chuanhua 89-1 , I + code IPP-10, I + code ZJ3265, I + code JS91 17, I +
  • the compounds of formula I according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which have a favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants.
  • Compounds of formula I may act against all or only individual developmental stages of normally sensitive, but also resistant, animal pests, such as insects or representatives of the order Acarina.
  • the insecticidal or acaricidal activity of the compounds can manifest itself directly, i. e. in destruction of the pests, which takes place either immediately or only after some time has elapsed, for example during ecdysis, or indirectly, for example in a reduced oviposition and/or hatching rate, a good activity corresponding to a destruction rate (mortality) of at least 50 to 60%.
  • Acarina for example, Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp,
  • Calipitrimerus spp. Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemus spp, Hyalomma spp., Ixodes spp., Olygonychus spp, Ornithodoros spp., Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp, Polyphagotarsonemus spp, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp, Tarsonemus spp. and Tetranychus spp. ;
  • Anoplura for example, Haematopinus spp., Linognathus spp., Pediculus spp.,
  • Adelphocoris lineolatus Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp., Clavigralla tomentosicollis, Creontiades spp, Distantiella theobroma, Dichelops furcatus, Dysdercus spp., Edessa spp, Euchistus spp., Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp, Margarodes spp, Murgantia histrionic,
  • Neomegalotomus spp Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp., Piezodorus spp, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp. , Thyanta spp , Triatoma spp. , and Vatiga illudens;
  • homoptera for example, Acyrthosium pisum, Adalges spp, Agalliana ensigera, Agonoscena targionii, Aleurodicus spp, Aleurocanthus spp, Aleurolobus barodensis,
  • pseudobrassicae Hyalopterus spp, Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis,
  • Macrosiphum spp. Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxera spp, Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria
  • Hymenoptera for example, Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp. and Vespa spp.;
  • Orthoptera for example, Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp. , Scapteriscus spp, and
  • Siphonaptera for example, Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis;
  • Thysanoptera for example, Calliothrips phaseoli, Frankliniella spp., Heliothrips spp, Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp; and/or
  • Thysanura for example, Lepisma saccharina.
  • Diabrotica spp. Dilopoderus spp. , Epilachna spp., Eremnus spp. , Heteronychus spp. , Lissorhoptrus spp. , Melolontha spp., Orycaephilus spp., Otiorhynchus spp., Phlyctinus spp. , Popillia spp. ,
  • Psylliodes spp. Rhizopertha spp., Scarabeidae, Sitotroga spp. , Somaticus spp. , Tanymecus spp. ,
  • Orthoptera for example, Gryllotalpa spp.
  • Anoplura for example, Haematopinus spp., Linognathus spp., Pediculus spp. , Pemphigus spp. and Phylloxera spp.;
  • Homoptera for example, Eriosoma larigerum
  • Hymenoptera for example, Acromyrmex, Atta spp. , Cephus spp. , Lasius spp. , Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.;
  • the invention also relates to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes
  • Hemicriconemoides species Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes,
  • the nematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp. and Pratylenchus spp. can be controlled by the present inventive compounds.
  • the controlling of animal parasites includes controlling external parasites that are parasitic to the surface of the body of the host animal (e.g., shoulders, armpits, abdomen, inner part of the thighs) and internal parasites that are parasitic to the inside of the body of the host animal (e.g. , stomach, intestine, lung, veins, under the skin, lymphatic tissue).
  • External parasitic or disease transmitting pests include, for example, chiggers, ticks, lice, mosquitoes, flies, mites and fleas.
  • Internal parasites include heartworms, hookworms and helminths.
  • the compounds of the invention may be particularly suitable for combating external parasitic pests.
  • the compounds of the invention may be suitable for systemic and/or non-systemic control of infestation or infection by parasites on animals.
  • the compounds of the invention may be suitable for combating parasitic invertebrate pests that infest animal subjects including those in the wild , livestock and agricultural working animals.
  • Livestock is the term used to refer (singularly or plurally) to a domesticated animal intentionally reared in an agricultural setting to make produce such as food or fiber, or for its labor; examples of livestock include cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, hens, turkeys, ducks and geese (e.g., raised for meat, milk, butter, eggs, fur, leather, feathers and/or wool).
  • the compounds of the invention may be suitable for combating parasitic invertebrate pests that infest companion animals and pets (e.g. , dogs, cats, pet birds and aquarium fish), research and experimental animals (e.g., hamsters, guinea pigs, rats and mice), as well as animals raised for/in zoos, wild habitats and/or circuses.
  • companion animals and pets e.g. , dogs, cats, pet birds and aquarium fish
  • research and experimental animals e.g., hamsters, guinea pigs, rats and mice
  • the animal is preferably a vertebrate, and more preferably a mammal, avian or fish.
  • the animal subject is a mammal (including great apes, such as humans).
  • Other mammalian subjects include primates (e.g. , monkeys), bovine (e.g. , cattle or dairy cows), porcine (e.g. , hogs or pigs), ovine (e.g., goats or sheep), equine (e.g. , horses), canine (e.g., dogs), feline (e.g. , house cats), camels, deer, donkeys, buffalos, antelopes, rabbits, and rodents (e.g.
  • Avians include Anatidae (swans, ducks and geese), Columbidae (e.g. , doves and pigeons), Phasianidae (e.g ., partridges, grouse and turkeys), Thesienidae (e.g. , domestic chickens), Psittacines (e.g., parakeets, macaws, and parrots), game birds, and ratites (e.g. , ostriches).
  • Anatidae swans, ducks and geese
  • Columbidae e.g. , doves and pigeons
  • Phasianidae e.g ., partridges, grouse and turkeys
  • Thesienidae e.g. , domestic chickens
  • Psittacines e.g., parakeets, macaws, and parrots
  • game birds
  • Birds treated or protected by the compounds of the invention can be associated with either commercial or noncommercial aviculture. These include Anatidae, such as swans, geese, and ducks, Columbidae, such as doves and domestic pigeons, Phasianidae, such as partridge, grouse and turkeys, Thesienidae, such as domestic chickens, and Psittacines, such as parakeets, macaws and parrots raised for the pet or collector market, among others.
  • Anatidae such as swans, geese, and ducks
  • Columbidae such as doves and domestic pigeons
  • Phasianidae such as partridge, grouse and turkeys
  • Thesienidae such as domestic chickens
  • Psittacines such as parakeets, macaws and parrots raised for the pet or collector market, among others.
  • fish is understood to include without limitation, the Teleosti grouping of fish, i.e. , teleosts. Both the Salmoniformes order (which includes the Salmonidae family) and the Perciformes order (which includes the Centrarchidae family) are contained within the Teleosti grouping . Examples of potential fish recipients include the Salmonidae, Serranidae, Sparidae, Cichlidae, and Centrarchidae, among others.
  • inventions are also contemplated to benefit from the inventive methods, including marsupials (such as kangaroos), reptiles (such as farmed turtles), and other economically important domestic animals for which the inventive methods are safe and effective in treating or preventing parasite infection or infestation.
  • marsupials such as kangaroos
  • reptiles such as farmed turtles
  • other economically important domestic animals for which the inventive methods are safe and effective in treating or preventing parasite infection or infestation.
  • Examples of parasitic invertebrate pests controlled by administering a pesticidally effective amount of the compounds of the invention to an animal to be protected include ectoparasites (arthropods, acarines, etc.) and endoparasites (helminths, e.g. , nematodes, trematodes, cestodes, acanthocephalans, etc.).
  • helminths e.g. , nematodes, trematodes, cestodes, acanthocephalans, etc.
  • the disease or group of diseases described generally as helminthiasis is due to infection of an animal host with parasitic worms known as helminths.
  • the term 'helminths' is meant to include nematodes, trematodes, cestodes and acanthocephalans.
  • Helminthiasis is a prevalent and serious economic problem with domesticated animals such as swine, sheep,
  • the group of worms described as nematodes causes widespread and at times serious infection in various species of animals.
  • Nematodes that are contemplated to be treated by the compounds of the invention include, without limitation, the following genera: Acanthocheilonema, Aelurostrongylus, Ancylostoma,
  • Crenosoma Dictyocaulus, Dioctophyme, Dipetalonema, Diphyllobothrium, Dirofilaria, Dracunculus, Enterobius, Filaroides, Haemonchus, Heterakis, Lagochilascaris, Loa, Mansonella, Muellerius, Necator, Nematodirus, Oesophagostomum, Ostertagia, Oxyuris, Parafilaria, Parascaris,
  • Physaloptera Protostrongylus, Setaria, Spirocerca, Stephanofilaria, Strongyloides, Strongylus, Thelazia, Toxascaris, Toxocara, Trichinella, Trichonema, Trichostrongylus, Trichuris, Uncinaria and Wuchereria.
  • Still other parasites may be located in other tissues such as the heart and blood vessels, subcutaneous and lymphatic tissue and the like.
  • Trematodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Alaria, Fasciola, Nanophyetus,
  • Cestodes that are contemplated to be treated by the invention and by the inventive methods include, without limitation, the following genera: Diphyllobothrium, Diplydium, Spirometra and Taenia.
  • Ancylostoma, Necator, Ascaris, Strongy hides, Trichinella, Capillaria, Trichuris and Enterobius Other medically important genera of parasites which are found in the blood or other tissues and organs outside the gastrointestinal tract are the filarial worms such as Wuchereria, Brugia, Onchocerca and Loa, as well as Dracunculus and extra intestinal stages of the intestinal worms Strongyloides and Trichinella.
  • the compounds of the invention may be effective against a number of animal ectoparasites (e.g., arthropod ectoparasites of mammals and birds).
  • Insect and acarine pests include, e.g. , biting insects such as flies and mosquitoes, mites, ticks, lice, fleas, true bugs, parasitic maggots, and the like.
  • Adult flies include, e.g. , the horn fly or Haematobia irritans, the horse fly or Tabanus spp. , the stable fly or Stomoxys calcitrans, the black fly or Simulium spp. , the deer fly or Chrysops spp. , the louse fly or Melophagus ovinus, and the tsetse fly or Glossina spp.
  • Parasitic fly maggots include, e.g. , the bot fly (Oestrus ovis and Cuterebra spp.), the blow fly or Phaenicia spp.
  • Mosquitoes include, for example, Culex spp., Anopheles spp. and Aedes spp.
  • Mites include Mesostigmalphatalpha spp. e.g., mesostigmatids such as the chicken mite, Dermalphanyssus galphallinalphae; itch or scab mites such as Sarcoptidae spp. for example, Salpharcoptes scalphabiei; mange mites such as Psoroptidae spp. including Chorioptes bovis and Psoroptes ovis; chiggers e.g. , Trombiculidae spp. for example the North American chigger,
  • mesostigmatids such as the chicken mite, Dermalphanyssus galphallinalphae
  • itch or scab mites such as Sarcoptidae spp. for example, Salpharcoptes scalphabiei
  • mange mites such as Psoroptidae spp. including Chorioptes bovis and Psoroptes ovis
  • Ticks include, e.g ., soft-bodied ticks including Argasidae spp. for example Argalphas spp. and Ornithodoros spp. ; hard-bodied ticks including Ixodidae spp. , for example Rhipicephalphalus sanguineus, Dermacentor variabilis, Dermacentor andersoni, Amblyomma americanum, Ixodes scapularis and other Rhipicephalus spp. (including the former Boophilus genera).
  • soft-bodied ticks including Argasidae spp. for example Argalphas spp. and Ornithodoros spp.
  • hard-bodied ticks including Ixodidae spp. , for example Rhipicephalphalus sanguineus, Dermacentor variabilis, Dermacentor andersoni, Amblyomma americanum, Ixodes scapularis and other Rhipicephalus spp. (including the former Bo
  • Lice include, e.g ., sucking lice, e.g. , Menopon spp.
  • biting lice e.g. , Haematopinus spp., Linognathus spp. and Solenopotes spp.
  • Fleas include, e.g. , Ctenocephalides spp. , such as dog flea (Ctenocephalides canis) and cat flea (Ctenocephalides felis); Xenopsylla spp. such as oriental rat flea (Xenopsylla cheopis); and Pulex spp. such as human flea (Pulex irritans).
  • Ctenocephalides spp. such as dog flea (Ctenocephalides canis) and cat flea (Ctenocephalides felis); Xenopsylla spp. such as oriental rat flea (Xenopsylla cheopis); and Pulex spp. such as human flea (Pulex irritans).
  • True bugs include, e.g. , Cimicidae or e.g. , the common bed bug (Cimex lectularius);
  • Triatominae spp. including triatomid bugs also known as kissing bugs; for example Rhodnius prolixus and Triatoma spp.
  • flies, fleas, lice, mosquitoes, gnats, mites, ticks and helminths cause tremendous losses to the livestock and companion animal sectors.
  • Arthropod parasites also are a nuisance to humans and can vector disease-causing organisms in humans and animals.
  • the compounds of the invention may also be effective against ectoparasites including: flies such as Haematobia (Lyperosia) irritans (horn fly), Simulium spp. (blackfly), Glossina spp. (tsetse flies), Hydrotaea irritans (head fly), Musca autumnalis (face fly), Musca domestica (house fly), Morellia simplex (sweat fly), Tabanus spp. (horse fly), Hypoderma bovis, Hypoderma lineatum, Lucilia sericata, Lucilia cuprina (green blowfly), Calliphora spp.
  • flies such as Haematobia (Lyperosia) irritans (horn fly), Simulium spp. (blackfly), Glossina spp. (tsetse flies), Hydrotaea irritans (head fly), Musca autumnalis (face fly), Musca domestic
  • Trombicula spp. and Otodectes cyanotis ear mites
  • Treatments of the invention are by conventional means such as by enteral administration in the form of, for example, tablets, capsules, drinks, drenching preparations, granulates, pastes, boli, feed-through procedures, or suppositories; or by parenteral administration, such as, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implants; or by nasal administration.
  • enteral administration in the form of, for example, tablets, capsules, drinks, drenching preparations, granulates, pastes, boli, feed-through procedures, or suppositories
  • parenteral administration such as, for example, by injection (including intramuscular, subcutaneous, intravenous, intraperitoneal) or implants; or by nasal administration.
  • compounds of the invention When compounds of the invention are applied in combination with an additional biologically active ingredient, they may be administered separately e.g. as separate compositions.
  • the biologically active ingredients may be administered simultaneously or sequentially.
  • the biologically active ingredients may be components of one composition.
  • the compounds of the invention may be administered in a controlled release form, for example in subcutaneous or orally adminstered slow release formulations.
  • a parasiticidal composition according to the present invention comprises a compound of the invention, optionally in combination with an additional biologically active ingredient, or N-oxides or salts thereof, with one or more pharmaceutically or veterinarily acceptable carriers comprising excipients and auxiliaries selected with regard to the intended route of administration
  • a suitable carrier is selected on the basis of compatibility with the one or more active ingredients in the composition, including such considerations as stability relative to pH and moisture content. Therefore of note are compounds of the invention for protecting an animal from an invertebrate parasitic pest comprising a parasitically effective amount of a compound of the invention, optionally in combination with an additional biologically active ingredient and at least one carrier.
  • the compounds of the invention can be formulated in suspension, solution or emulsion in oily or aqueous vehicles, and may contain adjuncts such as suspending , stabilizing and/or dispersing agents.
  • compositions for injection include aqueous solutions of water-soluble forms of active ingredients (e.g. , a salt of an active compound), preferably in physiologically compatible buffers containing other excipients or auxiliaries as are known in the art of pharmaceutical formulation. Additionally, suspensions of the active compounds may be prepared in a lipophilic vehicle. Suitable lipophilic vehicles include fatty oils such as sesame oil, synthetic fatty acid esters such as ethyl oleate and triglycerides, or materials such as liposomes.
  • Aqueous injection suspensions may contain substances that increase the viscosity of the suspension, such as sodium carboxy methyl cellulose, sorbitol, or dextran.
  • Formulations for injection may be presented in unit dosage form, e.g., in ampoules or in multi-dose containers.
  • the active ingredient may be in powder form for constitution with a suitable vehicle, e.g., sterile, pyrogen-free water, before use.
  • the compounds of the invention may also be formulated as a depot preparation.
  • Such long acting formulations may be administered by implantation (for example, subcutaneously or intramuscularly) or by intramuscular or subcutaneous injection.
  • the compounds of the invention may be formulated for this route of administration with suitable polymeric or hydrophobic materials (for instance, in an emulsion with a pharmacologically acceptable oil), with ion exchange resins, or as a sparingly soluble derivative such as, without limitation, a sparingly soluble salt.
  • the compounds of the invention can be delivered in the form of an aerosol spray using a pressurized pack or a nebulizer and a suitable propellant, e.g ., without limitation, dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane or carbon dioxide.
  • a suitable propellant e.g ., without limitation, dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane or carbon dioxide.
  • the dosage unit may be controlled by providing a valve to deliver a metered amount.
  • Capsules and cartridges of, for example, gelatin for use in an inhaler or insufflator may be formulated containing a powder mix of the compound and a suitable powder base such as lactose or starch.
  • the compounds of the invention may have favourable pharmacokinetic and
  • compositions for protecting an animal from an invertebrate parasite pest in a form for oral administration i.e. comprising, in addition to a parasiticidally effective amount of a compound of the invention, one or more carriers selected from binders and fillers suitable for oral administration and feed concentrate carriers).
  • the compounds of the invention can be formulated with binders/fillers known in the art to be suitable for oral administration compositions, such as sugars and sugar derivatives (e.g. , lactose, sucrose, mannitol, sorbitol), starch (e.g.
  • cellulose and derivatives e.g., methylcellulose, carboxymethylcellulose, ethylhydroxycellulose
  • protein derivatives e.g ., zein, gelatin
  • synthetic polymers e.g. , polyvinyl alcohol, polyvinylpyrrolidone
  • lubricants e.g ., magnesium stearate
  • disintegrating agents e.g., cross-linked polyvinylpyrrolidinone, agar, alginic acid
  • dyes or pigments can be added.
  • Pastes and gels often also contain adhesives (e.g. , acacia, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to aid in keeping the composition in contact with the oral cavity and not being easily ejected.
  • a composition of the present invention is formulated into a chewable and/or edible product (e.g. , a chewable treat or edible tablet).
  • a chewable and/or edible product e.g. , a chewable treat or edible tablet.
  • Such a product would ideally have a taste, texture and/or aroma favored by the animal to be protected so as to facilitate oral
  • the carrier is typically selected from high-performance feed , feed cereals or protein concentrates.
  • Such feed concentrate-containing compositions can, in addition to the parasiticidal active ingredients, comprise additives promoting animal health or growth, improving quality of meat from animals for slaughter or otherwise useful to animal husbandry.
  • additives can include, for example, vitamins, antibiotics, chemotherapeutics, bacteriostats, fungistats, coccidiostats and hormones.
  • the compound of the invention may also be formulated in rectal compositions such as suppositories or retention enemas, using, e.g. , conventional suppository bases such as cocoa butter or other g lycerides.
  • the formulations for the method of this invention may include an antioxidant, such asBHT (butylated hydroxytoluene).
  • the antioxidant is generally present in amounts of at 0.1 - 5 percent (wt/vol).
  • Some of the formulations require a solubilizer, such as oleic acid, to dissolve the active agent, particularly if spinosad is included.
  • Common spreading agents used in these pour-on formulations include isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated C12-C18 fatty alcohols, oleic acid , oleyl ester, ethyl oleate, triglycerides, silicone oils and dipropylene glycol methyl ether.
  • the pour-on formulations for the method of this invention are prepared according to known techniques. Where the pour-on is a solution, the parasiticide/insecticide is mixed with the carrier or vehicle, using heat and stirring if required. Auxiliary or additional ingredients can be added to the mixture of active agent and carrier, or they can be mixed with the active agent prior to the addition of the carrier. Pour-on formulations in the form of emulsions or suspensions are similarly prepared using known techniques.
  • Liposomes and emulsions are well-known examples of delivery vehicles or carriers for hydrophobic drugs.
  • organic solvents such as dimethylsulfoxide may be used , if needed.
  • “pesticidally effective amount”) will depend on such factors as the species of parasitic invertebrate pest to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like.
  • One skilled in the art can easily determine the pesticidally effective amount necessary for the desired level of parasitic invertebrate pest control.
  • the compounds of the invention are administered in a pesticidally effective amount to an animal, particularly a homeothermic animal, to be protected from parasitic invertebrate pests.
  • a pesticidally effective amount is the amount of active ingredient needed to achieve an observable effect diminishing the occurrence or activity of the target parasitic invertebrate pest.
  • the pesticidally effective dose can vary for the various compounds and compositions useful for the method of the present invention, the desired pesticidal effect and duration, the target parasitic invertebrate pest species, the animal to be protected, the mode of application and the like, and the amount needed to achieve a particular result can be determined through simple experimentation.
  • a dose of the compositions of the present invention administered at suitable intervals typically ranges from about 0.01 mg/kg to aboutl OO mg/kg, and preferably from about 0.01 mg/kg to about 30 mg/kg of animal body weight.
  • Suitable intervals for the administration of the compositions of the present invention to animals range from about daily to about yearly. Of note are administration intervals ranging from about weekly to about once every 6 months. Of particular note are monthly adminstration intervals (i.e. administering the compounds to the animal once every month).
  • the compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.8 ppm.
  • reaction mass was stirred at 75 °C for 15hour.
  • the reaction mass was filtered over celite bed, diluted with water (30 mL) and extracted with ethyl acetate (3 x 15 mL).
  • the combined organic layer was dried over sodium sulphate, filtered and concentrated under reduced pressure.
  • the crude products were purified by combiflash Rf, eluted with cyclohexane/ethyl acetate to obtain mixture of title compounds as a solid (0.070 g).

Abstract

L'invention concerne des composés de formule (I) dans laquelle les substituants sont tels que définis dans la revendication 1, et les sels, stéréoisomères, énantiomères, tautomères et N-oxydes de ces composés, acceptables au plan agrochimique, et leur utilisation en tant qu'insecticides.
PCT/EP2015/057289 2015-04-02 2015-04-02 Dérivés d'isoxazoline-styrène utilisés comme composés insecticides WO2016155831A1 (fr)

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WO2018071535A1 (fr) 2016-10-14 2018-04-19 Merial, Inc. Composés de vinyl-isoxazoline pesticides et parasiticides
CN109897006A (zh) * 2019-03-19 2019-06-18 扬州大学 一种甲基二磺隆的制备方法

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018071535A1 (fr) 2016-10-14 2018-04-19 Merial, Inc. Composés de vinyl-isoxazoline pesticides et parasiticides
US20190281829A1 (en) * 2016-10-14 2019-09-19 Boehringer Ingelheim Animal Health USA Inc. Pesticidal and parasiticidal vinyl isoxazoline compounds
CN110381738A (zh) * 2016-10-14 2019-10-25 勃林格殷格翰动物保健美国公司 农药的和杀寄生物的乙烯基异噁唑啉化合物
JP2019535655A (ja) * 2016-10-14 2019-12-12 ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド 殺虫性及び殺寄生虫性ビニルイソオキサゾリン化合物
US10653144B2 (en) 2016-10-14 2020-05-19 Boehringer Ingelheim Animal Health USA Inc. Pesticidal and parasiticidal vinyl isoxazoline compounds
CN110381738B (zh) * 2016-10-14 2021-07-16 勃林格殷格翰动物保健美国公司 农药的和杀寄生物的乙烯基异噁唑啉化合物
CN109897006A (zh) * 2019-03-19 2019-06-18 扬州大学 一种甲基二磺隆的制备方法
CN109897006B (zh) * 2019-03-19 2022-06-03 扬州大学 一种甲基二磺隆的制备方法

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