US20060106045A1 - Spiroindolinepiperidine derivatives - Google Patents

Spiroindolinepiperidine derivatives Download PDF

Info

Publication number
US20060106045A1
US20060106045A1 US10/517,957 US51795705A US2006106045A1 US 20060106045 A1 US20060106045 A1 US 20060106045A1 US 51795705 A US51795705 A US 51795705A US 2006106045 A1 US2006106045 A1 US 2006106045A1
Authority
US
United States
Prior art keywords
alkyl
optionally substituted
alkoxy
halogen
haloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/517,957
Other languages
English (en)
Inventor
David John Hughes
Paul Worthington
Charles Russell
Eric Clarke
James Peace
Mark Ashton
Thomas Coulter
Richard Roberts
Louis-Pierre Molleyres
Fredrik Cederbaum
Jerome Cassayre
Peter Maienfisch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Syngenta Participations AG
Syngenta Ltd
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9938602&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20060106045(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Individual filed Critical Individual
Publication of US20060106045A1 publication Critical patent/US20060106045A1/en
Assigned to SYNGENTA PARTICIPATIONS AG reassignment SYNGENTA PARTICIPATIONS AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ROBERTS, RICHARD SPURRING, CEDERBAUM, FREDRIK, MOLLEYRES, LOUIS-PIERRE, MAIENFISCH, PETER, CASSAYRE, JEROME
Assigned to SYNGENTA LIMITED reassignment SYNGENTA LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HUGHES, DAVID JOHN, CLARKE, ERIC DANIEL, PEACE, JAMES EDWARD, WORTHINGTON, PAUL ANTHONY, RUSSELL, CHARLES ADAM, ASHTON, MARK RICHARD, COULTER, THOMAS STEPHEN
Priority to US14/859,410 priority Critical patent/US9686990B2/en
Abandoned legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/11—Compounds covalently bound to a solid support

Definitions

  • the present invention relates to spiroindoline derivatives, to processes for preparing them, to insecticidal, acaricidal, molluscicidal and nematicidal compositions comprising them and to methods of using them to combat and control insect, acarine, mollusc and nematode pests.
  • Spiroindoline derivatives with pharmaceutical properties are disclosed in for example WO9825605, WO9429309, WO9828297 and WO9964002. Synthetic routes to selected compounds with pharmaceutical properties are described in Proc. Natl. Acad. Sci. USA (1995), 92, 7001, Tetrahedron (1997), 53, 10983 and Tetrahedron Letters (1997), 38, 1497. It has now surprisingly been found that certain spiroindolines have insecticidal properties.
  • the present invention therefore provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I): wherein Y is a single bond, C ⁇ O, C ⁇ S or S(O) q where q is 0, 1 or 2; R 1 is hydrogen, optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted heterocyclyloxy, cyan
  • 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.
  • Each alkyl moiety either alone or as part of a larger group is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or neo-pentyl.
  • the optional substituents on an alkyl moiety include one or more of halogen, nitro, cyano, NCS—, C 3-7 cycloalkyl (itself optionally substituted with C 1-6 alkyl or halogen), C 5-7 cycloalkenyl (itself optionally substituted with C 1-6 alkyl or halogen), hydroxy, C 1-10 alkoxy, C 1-10 alkoxy(C 1-10 )alkoxy, tri(C 1-4 )alkylsilyl(C 1-6 )alkoxy, C 1-6 alkoxycarbonyl(C 1-10 )alkoxy, C 1-10 haloalkoxy, aryl(C 1-4 )-alkoxy (where the aryl group is optionally substituted), C 3-7 cycloalkyloxy
  • Alkenyl and alkynyl moieties can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the ( E ) or ( Z )-configuration. Examples are vinyl, allyl and propargyl.
  • the optional substituents on alkenyl or alkynyl include those optional substituents given above for an alkyl moiety.
  • acyl is optionally substituted C 1-6 alkylcarbonyl (for example acetyl), optionally substituted C 2-6 alkenylcarbonyl, optionally substituted C 2-6 alkynylcarbonyl, optionally substituted arylcarbonyl (for example benzoyl) or optionally substituted heteroarylcarbonyl.
  • C 1-6 alkylcarbonyl for example acetyl
  • C 2-6 alkenylcarbonyl optionally substituted C 2-6 alkynylcarbonyl
  • arylcarbonyl for example benzoyl
  • heteroarylcarbonyl for example benzoyl
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkyl groups are alkyl groups which are substituted with one or more of the same or different halogen atoms and are, for example, CF 3 , CF 2 Cl, CF 3 CH 2 or CHF 2 CH 2 .
  • aryl and aromatic ring system refer to ring systems which may be mono-, bi- or tricyclic. Examples of such rings include phenyl, naphthalenyl, anthracenyl, indenyl or phenanthrenyl. A preferred aryl group is phenyl.
  • heteroaryl refers to an aromatic ring system 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 and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulphur.
  • groups include furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-tria
  • heterocycle and heterocyclyl refer to a non-aromatic ring containing up to 10 atoms including one or more (preferably one or two) heteroatoms selected from O, S and N.
  • examples of such rings include 1,3-dioxolane, tetrahydrofuran and morpholine.
  • the optional substituents on heterocyclyl include C 1-6 alkyl and C 1-6 haloalkyl as well as those optional substituents given above for an alkyl moiety.
  • Cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl.
  • Cycloalkenyl includes cyclopentenyl and cyclohexenyl.
  • cycloalkyl or cycloalkenyl include C 1-3 alkyl as well as those optional substituents given above for an alkyl moiety.
  • Carbocyclic rings include aryl, cycloalkyl and cycloalkenyl groups.
  • the optional substituents on aryl or heteroaryl are selected independently, from halogen, nitro, cyano, NCS—, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy-(C 1-6 )alkyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl (itself optionally substituted with C 1-6 alkyl or halogen), C 5-7 cycloalkenyl (itself optionally substituted with C 1-6 alkyl or halogen), hydroxy, C 1-10 alkoxy, C 1-10 alkoxy(C 1-10 )alkoxy, tri(C 1-4 )alkyl-silyl(C 1-6 )alkoxy, C 1-6 alkoxycarbonyl(C 1-10 )alkoxy, C 1-10 haloalkoxy, aryl(C 1-4 )alkoxy (where the aryl group is optional
  • aryl or heteroaryl include aryl carbonyl amino (where the aryl group is substituted by C 1-6 alkyl or halogen), (C 1-6 )alkyloxycarbonylamino (C 1-6 )alkyloxycarbonyl-N—(C 1-6 )alkylamino, aryloxycarbonylamino (where the aryl group is substituted by C 1-6 alkyl or halogen), aryloxycarbonyl-N—(C 1-6 )alkylamino, (where the aryl group is substituted by C 1-6 alkyl or halogen), arylsulphonylamino (where the aryl group is substituted by C 1-6 alkyl or halogen), arylsulphonyl-N—(C 1-6 )alkylamino (where the aryl group is substituted by C 1-6 alkyl or halogen), aryl-N—(C 1-6 )alkylamino (where the aryl
  • substituents are independently selected from halogen, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylthio, C 1-6 haloalkylthio, C 1-6 alkylsulfinyl, C 1-6 haloalkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 haloalkylsulfonyl, C 2-6 alkenyl, C 2-6 haloalkenyl, C 2-6 alkynyl, C 3-7 cycloalkyl, nitro, cyano, CO 2 H, C 1-6 alkylcarbonyl, C 1-6 alkoxycarbonyl, R 31 R 32 N or R 33 R 34 NC(O); wherein R 31 R 32 N or R 33 R 34 NC(O); wherein R 31
  • Haloalkenyl groups are alkenyl groups which are substituted with one or more of the same or different halogen atoms
  • dialkylamino substituents include those where the dialkyl groups together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further heteroatoms selected from O, N or S and which is optionally substituted by one or two independently selected (C 1-6 )alkyl groups.
  • heterocyclic rings are formed by joining two groups on an N atom, the resulting rings are suitably pyrrolidine, piperidine, thiomorpholine and morpholine each of which may be substituted by one or two independently selected (C 1-6 ) alkyl groups.
  • the optional substituents on an alkyl moiety include one or more of halogen, nitro, cyano, HO 2 C, C 1-10 alkoxy (itself optionally substituted by C 1-10 alkoxy), aryl(C 1-4 )alkoxy, C 1-10 alkylthio, C 1-10 alkylcarbonyl, C 1-10 alkoxycarbonyl, C 1-6 alkylaminocarbonyl, di(C 1-6 alkyl)aminocarbonyl, (C 1-6 )alkylcarbonyloxy, optionally substituted phenyl, heteroaryl, aryloxy, arylcarbonyloxy, heteroaryloxy, heterocyclyl, heterocyclyloxy, C 3-7 cycloalkyl (itself optionally substituted with (C 1-6 )alkyl or halogen), C 3-7 cycloalkyloxy, C 5-7 cycloalkenyl, C 1-6 alkylsulfonyl, C 1-6 alkyl
  • the optional substituents on alkenyl or alkynyl include one or more of halogen, C 3-7 cycloalkyl and aryl; the aryl group may be optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino.
  • a preferred optional substituent for heterocyclyl is C 1-6 alkyl.
  • the optional substituents for cycloalkyl include halogen, cyano and C 1-3 alkyl.
  • the optional substituents for cycloalkenyl include C 1-3 alkyl, halogen and cyano.
  • R 1 is hydrogen, optionally substituted alkyl, optionally substituted alkoxycarbonyl, optionally substituted alkylcarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted heterocyclyloxy, cyano, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, formyl, optionally substituted heterocyclyl, optionally substituted alkylthio or NR 13 R 14 where R 13 and R 14 are independently hydrogen
  • Another group of preferred compounds are those of formula (IB) which are compounds of formula (I) wherein Y is a single bond, C ⁇ O or S(O) q where q is 0, 1 or 2;
  • R 1 is hydrogen, C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 5-6 cycloalkenyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 3-6 alkenyloxy(C 1-6 )alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 2-6 alkenylcarbonyl-(C 1-6 )alkyl, C 2-6 alkynylcarbonyl(C 1-6
  • a further group of preferred compounds are those of formula (IC) which are compounds of formula (I) wherein Y is a single bond, C ⁇ O or S(O) q where q is 0, 1 or 2;
  • R 1 is hydrogen, C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 5-6 cycloalkenyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 3-6 alkenyloxy(C 1-6 )alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 2-6 alkenylcarbonyl-(C 1-6 )alkyl, C 2-6 alkynylcarbonyl(C 1-6
  • Another group of preferred compounds are those of formula (ID) which are compounds of formula (I) wherein Y is a single bond or C ⁇ O;
  • R 1 is hydrogen, C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 5-6 cycloalkenyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 3-6 alkenyloxy(C 1-6 )alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 2-6 alkenylcarbonyl-(C 1-6 )alkyl, C 2-6 alkynylcarbonyl(C 1-6 )alkyl, C 1-6 alkoxycarbonyl(
  • Yet another group of preferred compounds are those of formula (IE), which are compounds of formula (I) wherein Y, R 1 , R 2 , R 3 , R 4 , R 8 and n are as defined for compounds of formula IC; R 9 and R 10 are independently hydrogen, C 1-2 alkyl or halogen, and preferably all are hydrogen; and salts or N-oxides thereof.
  • formula (IE) are compounds of formula (I) wherein Y, R 1 , R 2 , R 3 , R 4 , R 8 and n are as defined for compounds of formula IC; R 9 and R 10 are independently hydrogen, C 1-2 alkyl or halogen, and preferably all are hydrogen; and salts or N-oxides thereof.
  • a further group of preferred compounds are those of formula (IF), which are compounds of formula (I) wherein Y, R 1 , R 4 , R 8 , R 9 , R 10 and n are as defined for compounds of formula (IE) and R 2 and R 3 are independently hydrogen, halogen, C 1-2 alkyl, C 1-2 haloalkyl, C 1-2 alkoxy, cyano, or R 2 and R 3 together are ⁇ O, or R 2 and R 3 together with the atoms to which they are attached form a 4, 5, 6, or 7 membered carbocylic or heterocyclic ring; and salts or N-oxides thereof.
  • formula (IF) are compounds of formula (I) wherein Y, R 1 , R 4 , R 8 , R 9 , R 10 and n are as defined for compounds of formula (IE) and R 2 and R 3 are independently hydrogen, halogen, C 1-2 alkyl, C 1-2 haloalkyl, C 1-2 alkoxy, cyano, or R
  • IG are compounds of formula () wherein Y, R 1 , R 2 , R 3 , R 8 , R 9 , R 10 and n are as defined for compounds of formula (IF) and each R 4 is independently halogen, nitro, cyano, C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 alkoxycarbonyl(C 1-6 )alkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 1-6 alkylaminocarbonyl(C 1-6 )alkyl, di(C 1-6 )alkylaminocarbonyl(C 1-6 )alkyl, phenyl(C 1-6 )alkyl (wherein the phenyl group is optionally substituted by halogen,
  • a further group of preferred compounds are those of formula (IG′), which are compounds of formula (I) wherein Y, R 1 , R 2 , R 3 , R 8 , R 9 , R 10 and n are as defined for compounds of formula (IB) and each R 4 is independently halogen, nitro, cyano, C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 1-6 alkoxycarbonyl(C 1-6 )alkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 1-6 alkylaminocarbonyl(C 1-6 )alkyl, di(C 1-6 )alkylaminocarbonyl(C 1-6 )alkyl, phenyl(C 1-6 )alkyl (wherein the phenyl group is optionally substituted by
  • R 1 is C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 5-6 cycloalkenyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )-alkyl, C 3-6 alkenyloxy(C 1-6 )alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 2-6 alkenylcarbonyl(C 1-6 )alkyl
  • Another group of preferred compounds are those of formula (IH′), which are compounds of formula (I) wherein R 2 , R 3 , R 4 , R 8 , R 9 , R 10 and n are as defined for compounds of formula (IG′) and R 1 is C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 5-6 cycloalkenyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )-alkyl, C 3-6 alkenyloxy(C 1-6 )alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 2-6 alkenylcarbonyl(C 1-6 )alkyl, C 2-6 alkynyl
  • a further group of preferred compounds are those of formula (IJ), which are compounds of formula (I) wherein Y, R 1 , R 2 , R 3 , R 4 , R 9 , R 10 and n are as defined for compounds of formula (IH) and R 8 is C 1-10 alkyl optionally substituted by C 1-6 alkoxy, halogen or phenyl (itself optionally substituted by halogen, C 1-4 alkyl or C 1-4 alkoxy), C 2-6 alkenyl optionally substituted by C 1-6 alkoxy, halogen or phenyl (itself optionally substituted by halogen, C 1-4 alkyl or C 1-4 alkoxy) or C 2-6 alkyl optionally substituted by C 1-6 alkoxy, halogen or phenyl (itself optionally substituted by halogen, C 1-4 alkyl or C 1-4 alkoxy); and salts or N-oxides thereof.
  • a further group of preferred compounds are those of formula (IJ′), which are compounds of formula (I) wherein Y, R 1 , R 2 , R 3 , R 4 , R 9 , R 10 and n are as defined for compounds of formula (IH′) and R 8 is C 1-6 alkyl optionally substituted by phenyl or heteroaryl (the phenyl and heteroaryl groups being optionally substituted halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino); or —C(R 51 )( 52 )—[CR 53 ⁇ CR 54 ] z R 55 where z is 1 or 2, R 51 and R 52 are each independently H, halo or C 1-2 alkyl, R 53 and R 54 are each independently H, halogen, C 1-4 alkyl or C 1-4 haloalkyl and R 55 is
  • Still another preferred group of compounds are those of formula (IK), which are compounds of formula (I) wherein Y is a single bond, C ⁇ O or S(O) q where q is 0, 1 or 2; R 1 is C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 3-6 alkenyloxy-(C 1-6 )alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 2-6 alkenylcarbonyl(C 1-6 )alkyl, C 2-6 alkynylcarbonyl(C 1-6 )alkyl, C 1-6 alkoxycarbonyl(C 1-6 )alky
  • Still another preferred group of compounds are those of formula (IL), which are compounds of formula (I) wherein Y is a single bond or C ⁇ O;
  • R 1 is C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 3-6 alkenyloxy-(C 1-6 )alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 2-6 alkenylcarbonyl(C 1-6 )alkyl, C 2-6 alkynylcarbonyl(C 1-6 )alkyl, C 1-6 alkoxycarbonyl(C 1-6 )alkyl, C 3-6 alkenyloxycarbonyl(
  • An even more preferred group of compounds are those of formula (IM), which are compounds of formula (I) wherein Y is a single bond or C ⁇ O;
  • R 1 is C 1-8 alkyl, C 1-6 haloalkyl, C 1-6 cyanoalkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 3-6 alkenyloxy-(C 1-6 )-alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcarbonyl-(C 1-6 )alkyl, C 2-6 alkenylcarbonyl(C 1-6 )alkyl, C 2-6 alkynylcarbonyl(C 1-6 )alkyl, C 1-6 alkoxycarbonyl(C 1-6 )alkyl, C 3-6 alkenyloxycarbon
  • Y is a single bond, C ⁇ O, C ⁇ S or S(O) q where q is 0, 1 or 2.
  • Y is a single bond, C ⁇ O or SO 2 .
  • Y is a single bond or C ⁇ O, especially C ⁇ O.
  • R 1 is preferably hydrogen, C 1-6 alkyl, C 1-6 cyanoalkyl, C 1-6 haloalkyl, C 3-7 cycloalkyl(C 1-4 )alkyl, C 1-6 alkoxy(C 1-6 )alkyl, heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group may be optionally substituted by halo, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 1-6 alkylthio, C 1-6 alkoxycarbonyl, C 1-6 alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the heteroaryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen), ary
  • R 1 is hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group may be optionally substituted by halo, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 1-6 alkylthio, C 1-6 alkoxycarbonyl, C 1-6 alkylcarbonylamino, arylcarbonyl, or two adjacent positions on the heteroaryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen), phenyl(C 1-6 )alkyl (wherein the phenyl group may be optionally substituted by halogen),
  • R 1 is C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy(C 1-6 )alkyl, heteroaryl(C 1-3 )alkyl (wherein the heteroaryl group may be optionally substituted by halo, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, C 1-6 haloalkoxy, C 1-6 alkylsulfonyl, C 1-6 alkoxycarbonyl, or two adjacent positions on the heteroaryl system may be cyclised to form a 5, 6 or 7 membered carbocyclic or heterocyclic ring, itself optionally substituted with halogen), phenyl(C 1-3 )alkyl (wherein the phenyl group may be optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2
  • R 1 is C 1-6 alkyl, C 1-6 haloalkyl, heteroaryl(C 1-3 )alkyl (wherein the heteroaryl group maybe optionally substituted by halo, cyano, C 1-6 alkyl, C 1-6 haloalkyl) where the heteroaryl group is a pyridine, pyrimidine, pyrazine or pyridazine ring, heteroaryl (optionally substituted by halo, cyano, C 1-6 alkyl, C 1-6 haloalkyl) where the heteroaryl group is a pyridine, pyrimidine, pyrazine or pyridazine ring, C 1-6 alkoxy or heterocyclyl (optionally substituted by halo, cyano, C 1-3 alkyl, C 1-3 haloalkyl, or C 1-3 alkoxy).
  • R 1 is pyridyl (optionally substituted by halo, C 1-3 alkyl or C 1-3 haloalkyl) or C 1-6 alkoxy, especially halo-substituted pyridyl.
  • R 2 and R 3 are independently hydrogen or C 1-4 alkyl.
  • R 2 and R 3 are independently hydrogen or methyl.
  • R 2 is hydrogen and R 3 is hydrogen or methyl
  • R 2 and R 3 are both hydrogen.
  • each R 4 is independently halogen, cyano, C 1-8 alkyl, C 1-8 haloalkyl, C 1-6 cyanoalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 3-7 cycloalkyl(C 1-6 )alkyl, C 5-6 cycloalkenyl(C 1-6 )alkyl, C 3-6 alkenyloxy(C 1-6 )alkyl, C 3-6 alkynyloxy(C 1-6 )alkyl, aryloxy(C 1-6 )alkyl, C 1-6 carboxyalkyl, C 1-6 alkylcarbonyl(C 1-6 )alkyl, C 2-6 alkenylcarbonyl(C 1-6 )alkyl, C 2-6 alkynylcarbonyl(C 1-6 )-alkyl, C 1-6 alkoxycarbonyl(C 1-6 )alkyl, C 3-6 alkenyloxycarbonyl(C 1-6 )alky
  • each R 4 is independently halogen, cyano, C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 cyanoalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 2-6 alkynyl, trimethylsilyl(C 2-6 )alkynyl, C 1-6 alkoxycarbonyl, C 3-7 cycloalkyl, C 1-3 alkyl (C 3-7 ) cycloalkyl, phenyl (optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heterocyclyl (optionally substituted by halo, nitro, cyano, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy or C 1-6 haloalkoxy), C 1-8 alk
  • each R 4 is independently halogen, cyano, C 1-8 alkyl, C 1-8 haloalkyl, C 1-8 cyanoalkyl, C 1-6 alkoxy(C 1-6 )alkyl, C 2-6 alkynyl, heterocyclyl (optionally substituted by C 1-6 alkyl), C 1-8 alkoxy, C 1-6 haloalkoxy, phenoxy (optionally substituted by halo, cyano, C 1-3 alkyl or C 1-3 haloalkyl), heteroaryloxy (optionally substituted by halo, cyano, C 1-3 alkyl or C 1-3 haloalkyl), di(C 1-8 )alkylamino or 2 adjacent groups R 4 together with the carbon atoms to which they are attached form a 4, 5, 6,or 7 membered carbocylic or heterocyclic ring which may be optionally substituted by halogen; n is 0, 1, 2, 3 or 4;
  • each R 4 is independently fluoro, chloro, bromo, cyano, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 cyanoalkyl or C 1-3 alkoxy(C 1-3 )alkyl; n is 0, 1 or 2;
  • each R 4 is independently fluoro, chloro, bromo, C 1-4 alkyl or C 1-4 haloalkyl; n is 1 or 2.
  • R 8 is C 1-10 alkyl, C 1-10 haloalkyl, aryl(C 1-6 )alkyl (wherein the aryl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group is optionally substituted halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), arylcarbonyl-(C 1-6 )alkyl (wherein the aryl group may be optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl,
  • R 8 is more preferably C 1-6 alkyl, C 1-6 haloalkyl, aryl(C 1-4 )alkyl (wherein the aryl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), C 2-6 alkenyl, aryl(C 2-6 )alkenyl (wherein the aryl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4
  • R 8 is phenyl(C 1-4 )alkyl (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heteroaryl(C 1-6 )alkyl (wherein the heteroaryl group is optionally substituted halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), phenyl(C 2-6 )alkenyl (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , ary
  • R 8 is phenylCH 2 — (wherein the phenyl group is optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), heteroaryl CH 2 — (wherein the heteroaryl group is a bicyclic group optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino), or —C(R 51 )(R 52 )—[CR 53 ⁇ ]z-R 55 where z is 1 or 2, R 51 and R 52 are each independently H, halo or C 1-2 alkyl, R 53 and R 54 are each independently H, halogen, C 1-4 alkyl or C
  • R 8 is —C(R 51 )(R 52 )—[CR 53 ⁇ CR 54 ]z-R 55 where z is 1 or 2, preferably 1, R 51 and R 52 are each independently H, halo or C 1-2 alkyl, R 53 and R 54 are each independently H, halogen, C 1-4 alkyl or C 1-4 haloalkyl and R 55 is phenyl substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino or heteroaryl substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino
  • R 9 and R 10 are both hydrogen.
  • R 51 and R 52 are preferably hydrogen.
  • R 53 and R 54 are preferably hydrogen or halogen, especially hydrogen.
  • R 55 is preferably phenyl substituted with one to three substituents selected from halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino
  • novel compounds of formula (I) are novel and as such form a further aspect of the invention.
  • novel compounds of formula (IK) as defined above and salts or N-oxides thereof provided that R 8 is not methyl and YR 1 is not SO 2 CH 3 , methyl, ethyl, phenyl or fluoro-substituted phenyl.
  • R 1 is C 1-6 alkyl, C 1-6 haloalkyl, heteroaryl(C 1-3 )alkyl (wherein the heteroaryl group may be optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino and the heteroaryl group is a pyridine, pyrimidine, pyrazine or pyridazine ring), heteroaryl (optionally substituted by halogen, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 haloalkyl, C 1-4 haloalkoxy, CN, NO 2 , aryl, heteroaryl, amino or dialkylamino and where the heteroaryl group is a pyridine, pyridine, pyridine, pyr
  • Table I provides 301 compounds of formula Ia
  • Table II provides 301 compounds of formula Ib wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table III provides 301 compounds of formula Ic wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table IV provides 301 compounds of formula Id wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table V provides 301 compounds of formula Ie wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table VI provides 301 compounds of formula If wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table VII provides 301 compounds of formula Ig wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table VIII provides 301 compounds of formula Ih wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table IX provides 301 compounds of formula Ii wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table X provides 301 compounds of formula Ij wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XI provides 301 compounds of formula Ik wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XII provides 301 compounds of formula Il wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XIV provides 301 compounds of formula In wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XV provides 301 compounds of formula Io wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are give in Table 1
  • Table XVI provides 301 compounds of formula Ip wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XVII provides 301 compounds of formula Iq wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XVIII provides 301 compounds of formula Ir wherein the values of R 8 , R 4a , R 4b , R4 and R 4d are given in Table 1
  • Table XIX provides 301 compounds of formula Is wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XX provides 301 compounds of formula It wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XXI provides 301 compounds of formula Iu wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XXII provides 301 compounds of formula Iv wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XXIII provides 301 compounds of formula Iw wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XXIV provides 301 compounds of formula Ix wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XXV provides 301 compounds of formula Iy wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XXVI provides 301 compounds of formula Iz wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XXVII provides 301 compounds of formula Iaa wherein the values of R 8 , R 4a , R 4b , R 4c and R 4d are given in Table 1
  • Table XXVIIl provides 270 compounds of formula Iab
  • Table XXIX provides 214 compounds of formula Iac
  • Table XXX provides 121 compounds of formula Iad (Iad) R 4 n R53 R54 R S n Y R1 XXX-1 6-OCF 3 H H 4-Cl C(O) Me XXX-2 6-OCF 3 H H 4-Cl C(O) 2-chloropyrid-4-yl XXX-3 4-OCF 3 H H 4-Cl C(O) Me XXX-4 6-OCF 2 CHF 2 H H H 4-Cl C(O) Me XXX-5 4-OCF 2 CHF 2 H H H 4-Cl C(O) Me XXX-6 4-OCF 3 H H H 4-Cl C(O) 2-chloropyrid-4-yl XX-7 6-OCF 2 CHF 2 H H H 4-Cl C(O) 2-chloropyrid-4-yl XX-8 4-OCF 2 CHF 2 H H H 4-Cl C(O) 2-chloropyrid-4-yl XX-9 7-O—Ph H H
  • Table XXXI provides 8 compounds of formula Iae (Iae) R 4 n R53 R54 Rt Y R1 XXXI-1 5-Cl H H 5-trifluoromethyl- C(O) 2-chloropyrid- pyrid-2-yl 4-yl XXXI-2 5-F H H 5-chloro- C(O) 2-chloropyrid- thiophen-2-yl 4-yl XXXI-3 5-Cl H H thiophen-2-yl C(O) 2-chloropyrid- 4-yl XXXI-4 5-Cl H H naphtha-2-yl C(O) 2-chloropyrid- 4-yl XXXI-5 5-Cl H H —CH ⁇ CH- C(O) 2-chloropyrid- phenyl 4-yl XXXI-6 5-Cl H H H benzothiophen-2- C(O) 2-chloropyrid- yl 4-yl
  • Table XXXII provides 10 compounds of formula Iaf (Iaf) R 4 n Ru Y R1 XXXII-1 5-Cl 4-F-Ph C(O) 2-chloropyrid-4-yl XXXII-2 5-Cl 4-OCF 3 -Ph C(O) 2-chloropyrid-4-yl XXXII-3 5-Cl 4-Cl-Ph C(O) 2-chloropyrid-4-yl XXXII-4 5-F 6-F-naphth-2-yl C(O) 2-chloropyrid-4-yl XXXII-5 5-Cl —CH(OH)CH 2 O-4-Cl- C(O) 2-chloropyrid-4-yl Ph XXXII-6 5-Cl —C(Me) ⁇ NO-Ph C(O) 2-chloropyrid-4-yl XXII-7 5-Cl 5-Cl-benzoxazol
  • the compounds of the invention may be made in a variety of ways. For example they may be made by the reactions summarised in Scheme I.
  • a compound of formula 1 may be synthesised from compounds of formula 2a or 2b by reaction with an alkylating agent of the formula R8-L, where L is chloride, bromide, iodide or a sulfonate (e.g.
  • mesylate or tosylate or similar leaving group at a temperature of between ambient temperature and 100° C., typically 65° C., in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane in the presence of a tertiary amine base such as triethylamine or diisopropylethylamine and optionally catalysed by halide salts such as sodium iodide, potassium iodide or tetrabutylammonium iodide.
  • organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane
  • a tertiary amine base such as triethylamine or diisopropylethylamine
  • halide salts such as sodium iodide, potassium iodide or tetrabutylammonium iodide.
  • a compound of formula 2a or 2b may be reacted with an aldehyde of the formula RCHO at a temperature between ambient temperature and 100° C. in an organic solvent such as tetrahydrofuran or ethanol or mixtures of solvents in the presence of a reducing agent such as borane-pyridine complex, sodium borohydride, sodium (triacetoxy)borohydride, sodium cyanoborohydride or such like, to produce a compound of formula 1 where R8 is CH 2 —R.
  • a reducing agent such as borane-pyridine complex, sodium borohydride, sodium (triacetoxy)borohydride, sodium cyanoborohydride or such like
  • a compound of formula 2a or 2b may be reacted with paraformaldehyde and a boronic acid of the formula R—B(OH) 2 at a temperature between ambient temperature and 1 00° C. in an organic solvent such as ethanol, 1,4dioxane or water to produce a compound of formula 1 where R8 is CH 2 —R.
  • a compound of formula 2a may be obtained from a compound of formula 3 by reaction with an acid such as trifluoroacetic acid at ambient temperature in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane followed by neutralisation of the reaction mixture with an aqueous solution of an inorganic base such as sodium carbonate, sodium bicarbonate or similar compound.
  • an acid such as trifluoroacetic acid at ambient temperature in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane followed by neutralisation of the reaction mixture with an aqueous solution of an inorganic base such as sodium carbonate, sodium bicarbonate or similar compound.
  • a compound of formula 2b may be formed by reaction of a compound of formula 3 with an acid such as trifluoroacetic acid at ambient temperature in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane followed by evaporation of the solvents and trituration with organic solvents such as ether or hexane.
  • an acid such as trifluoroacetic acid
  • organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane
  • Compounds of formula 3 may be obtained from compounds of formula 4 by reaction with a suitable electrophilic species.
  • Compounds of formula 3 where Y is a carbonyl group may be formed by the reaction of compounds of formula 4 with a carboxylic acid derivative of formula R1-C(O)-Z where Z is chloride, hydroxy, alkoxy or acyloxy at a temperature between 0° C. and 150° C.
  • Compounds of formula 3 where Y is a group of formula S(O) q may be formed from compounds of formula 4 by treatment with compounds of formula of R1-S(O) q —Cl under similar conditions.
  • Compounds of formula 3 where Y is a thiocarbonyl group and R1 is an amino substituent of formula R′—NH— may be formed by the reaction of compounds of formula 3 with an isothiocyanate of formula R′—N ⁇ C ⁇ S under similar conditions.
  • compounds of formula 3 where Y is a thiocarbonyl group and R1 is a carbon substituent may be formed by treatment of compounds of formula 3 where Y is a carbonyl group and R1 is a carbon substituent with a suitable thionating agent such as Lawesson's reagent.
  • acid derivatives of the formula R1-C(O)-Z, isocyanates of formula R′—N ⁇ C ⁇ O, isothiocyanates of formula R′—N ⁇ C ⁇ S and sulfur electrophiles of formula R1-S(O) q —Cl are either known compounds or may be formed from known compounds by known methods by a person skilled in the art.
  • Compounds of formula 4 may be obtained by reacting compounds of formula 5 with compounds of formula 6 at a temperature of between 0° C. and 100° C. in an organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane in the presence of an acid such as hydrochloric acid or trifluoroacetic acid and a co-solvent such as water, methanol or ethanol, or in the presence of a Lewis acidic metal salt such as a zinc(II) dihalide.
  • the intermediates formed (compounds of formula 4a) are subsequently treated with a nucleophile R3-M (where M is a metallic species.
  • R3-M is for example a Grignard reagent) or, when R3 is hydrogen, a reducing agent such as sodium borohydride, sodium (triacetoxy)borohydride, sodium cyanoborohydride or similar at ambient temperature in organic solvent such as ethanol or chloroform.
  • a reducing agent such as sodium borohydride, sodium (triacetoxy)borohydride, sodium cyanoborohydride or similar at ambient temperature in organic solvent such as ethanol or chloroform.
  • Compounds of formula 6 may be obtained from compounds of formula 7 by reaction with a 1-alkoxy substituted phosphonium salt such as methoxymethyl(triphenyl)phosphonium chloride and a base such as potassium tert-butoxide at a temperature of 0° C. to room temperature in tetrahydrofuran.
  • a 1-alkoxy substituted phosphonium salt such as methoxymethyl(triphenyl)phosphonium chloride
  • a base such as potassium tert-butoxide
  • Compounds of formula 5 and 7 are either known compounds or may be obtained from known compounds by known techniques.
  • a compound of formula 1′ may be obtained from a compound of formula 8 by reaction with an acid chloride or chloroformate of the formula R1COCl at a temperature between 0 ° C. and ambient in organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane in the presence of a tertiary amine base such as triethylamine or diisopropylethylamine.
  • a compound of formula 1′ may be obtained from a compound of formula 8 by reaction with a carboxylic acid of the formula R1COOH and a standard coupling agent such as 2-chloro-1,3-dimethyl-2-imidazolium hexafluorophosphate, or carbodiimide reagents such as dicyclohexylcarbodiimide or 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride at a temperature between 0° C. and ambient in organic solvent such as dichloromethane or tetrahydrofuran in the presence of a tertiary amine base such as triethylamine or diisopropylethylamine.
  • a standard coupling agent such as 2-chloro-1,3-dimethyl-2-imidazolium hexafluorophosphate
  • carbodiimide reagents such as dicyclohexylcarbodiimide or 1-(
  • a compound of formula 1′ may alternatively be obtained from a compound of formula 8 by reaction with a isocyanate or isothiocyanate of the formula RNCO or RNCS respectively at a temperature between 0° C. and ambient in organic solvent such as dichloromethane or tetrahydrofuran, optionally in the presence of a tertiary amine base such as triethylamine or diisopropylethylamine.
  • a compound of formula 1′ may also be obtained from a compound of formula 8 by reaction with a sulfonyl chloride of the formula R1SO 2 Cl at a temperature between 0° C. and ambient in organic solvent such as dichloromethane or tetrahydrofuran, in the presence of a tertiary amine base such as triethylamine or diisopropylethylamine.
  • a compound of formula 1′ may be obtained from a compound of formula 8 by reaction with an aryl or heteroaryl compound of formula Ar-L where L is a leaving group such as halide (especially fluoride), such as a 2-halopyridine, a 2-halopyrimidine, a 4-halopyridine, a 2-halopyrazine or such like at a temperature between 50° C. and 150° C. in a solvent such as dimethylsulfoxide in the presence of a strong base such as sodium hydride.
  • L is a leaving group such as halide (especially fluoride), such as a 2-halopyridine, a 2-halopyrimidine, a 4-halopyridine, a 2-halopyrazine or such like at a temperature between 50° C. and 150° C. in a solvent such as dimethylsulfoxide in the presence of a strong base such as sodium hydride.
  • Compounds of formula 8 may be obtained by reacting compounds of formula 9 with compounds of formula 5 (in scheme I) at a temperature of between ambient and 100° C. in organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane in the presence of an acid such as trifluoroacetic acid for typically 4 to 12 hours, followed by addition of a reducing agent such as triethylsilane and reaction at a temperature of ambient to 100° C. until the reaction is complete.
  • organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane
  • an acid such as trifluoroacetic acid
  • a reducing agent such as triethylsilane
  • Compounds of formula 8 may be obtained by reacting compounds of formula 9 with compounds of formula 5 at a temperature of between 0° C. and 100° C. in organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane in the presence of an acid such as hydrochloric acid, or trifluoroacetic acid and a co-solvent of either water or methanol or ethanol, or in the presence of a Lewis acidic metal salt such as zinc(II) dihalide.
  • organic solvent such as dichloromethane, chloroform or 1,2-dichloroethane
  • an acid such as hydrochloric acid, or trifluoroacetic acid
  • a co-solvent of either water or methanol or ethanol or in the presence of a Lewis acidic metal salt such as zinc(II) dihalide.
  • the intermediates formed are subsequently treated with a reducing agent such as sodium borohydride, sodium (triacetoxy)borohydride, sodium cyanoborohydride or such like at ambient temperature in organic solvent such as ethanol or chloroform.
  • a reducing agent such as sodium borohydride, sodium (triacetoxy)borohydride, sodium cyanoborohydride or such like at ambient temperature in organic solvent such as ethanol or chloroform.
  • Compounds of formula 8 may also be obtained by the hydrolysis of compounds of formula 1a (which are also a sub-set of compounds of formula 1) preferably with an aqueous acid, typically 6 N hydrochloric acid at reflux temperature.
  • Compounds of formula 9 may be obtained from compounds of formula 10 by reaction with methoxymethyl(triphenyl)phosphonium chloride or the corresponding bromide salt and a base such as potassium tert-butoxide at a temperature of 0° C. to ambient in tetrahydrofuran.
  • Compounds of formula 10 may be obtained by reacting compounds of formula 11 with an aqueous solution of acid, typically 6 N hydrochloric acid at reflux temperature.
  • Compounds of formula 11 may be obtained from compounds of formula 12 by reaction with an electrophile of the formula R8-L, where L is chloride, bromide, iodide or a sulfonate (e.g. mesylate or tosylate) or similar leaving group at between ambient temperature and 100° C., typically around 60° C.
  • L is chloride, bromide, iodide or a sulfonate (e.g. mesylate or tosylate) or similar leaving group at between ambient temperature and 100° C., typically around 60° C.
  • a tertiary amine base such as triethylamine or diisopropylethylamine and optionally catalysed by halide salts such as sodium iodide, potassium iodide or tetrabutylammonium iodide.
  • Compounds of formula 12 are known compounds or may be obtained from known compounds by known techniques.
  • the compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests.
  • the pests which may be combated and controlled by the use of the invention compounds include those pests associated with agriculture (which term includes the growing of crops for food and fibre products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber); those pests associated with the damage of man-made structures and the transmission of diseases of man and animals; and also nuisance pests (such as flies).
  • 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.
  • the invention therefore provides a method of combating and 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, or to a plant susceptible to attack by a pest,
  • the compounds of formula (I) are preferably used against insects, acarines or nematodes.
  • plant as used herein includes seedlings, bushes and trees.
  • a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA).
  • SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting).
  • compositions both solid and liquid formulations
  • the composition is generally used for the control of pests such that a compound of formula (I) is applied at a rate of from 0.1 g to 1 kg per hectare, preferably from 1 g to 6 kg 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 10 g (for example 0.001 g or 0.05 g), preferably 0.005 g to 10 g, more preferably 0.005 g to 4 g, 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, acaricidal, nematicidal or molluscicidal composition.
  • the invention provides a method of combating and controlling pests at a locus which comprises treating the pests or the locus of the pests with an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a composition comprising a compound of formula (I).
  • the compounds of formula (I) are preferably used against insects, acarines or nematodes.
  • 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 l0 formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (I).
  • Dustable powders may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
  • solid diluents for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers
  • Soluble powders may be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulphate) 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 sulphate
  • 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, sulphates or phosphates) and drying if necessary.
  • a hard core material such as sands, silicates, mineral carbonates, sulphates 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 crystallisation in a spray tank.
  • Emulsifiable concentrates or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents).
  • Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by 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), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as C 8 -C 10 fatty acid dimethylamide) and chlorinated hydrocarbons.
  • 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 cycl
  • An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment.
  • Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70° C.) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion.
  • Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.
  • Microemulsions 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 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-pressurised, 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 polymerisation 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 sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di-isopropyl- and tri-isopropyl-naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally
  • 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 vapour 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 fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers).
  • fertilisers for example nitrogen-, potassium- or phosphorus-containing fertilisers.
  • Suitable formulation types include granules of fertiliser.
  • the mixtures suitably contain up to 25% by weight of the compound of formula (I).
  • the invention therefore also provides a fertiliser composition comprising a fertiliser 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; synergise 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:
  • 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 hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).
  • acaricidal ovo-larvicides such as clofentezine, flubenzimine, hexythiazox or tetradifon
  • acaricidal motilicides such as dicofol or propargite
  • acaricides such as bromopropylate or chlorobenzilate
  • growth regulators such
  • fungicidal compounds which may be included in the composition of the invention are (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide (SSF-129), 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide, ⁇ -[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]- ⁇ -butyrolactone, 4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide (IKF-916, cyamidazosulfamid), 3-5-dichloro-N—(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH-7281, zoxamide), N-allyl4,5,-dimethyl-2-
  • 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.
  • Step 1 Preparation of 4-methoxymethylenepiperidine-1-carboxylic acid tert-butyl ester
  • Step 2 Preparation of 5-chlorospiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butyl ester
  • Trifluoroacetic acid (12 ml) was added to a stirred solution of 4-methoxymethylene-piperidine-1-carboxylic acid tert-butyl ester (12.5 g), 4-chlorophenylhydrazine hydrochloide (9.75 g) and ethanol (1 ml) in chloroform (1200 ml) at 4° C. under an atmosphere of nitrogen. The mixture was then stirred at 50° C. overnight, turning a dark green colour. The reaction was quenched with concentrated ammonia solution (200 ml) in ice water (500 ml), the organic layer turning orange. The organic layer was separated and the aqueous was further extracted twice with dichloromethane.
  • Step 3 Preparation of 1-acetyl-5-chlorospiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butyl ester
  • Trifluoroacetic acid 25 ml was added to a stirred solution of 1-acetyl-5-chlorospiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butyl ester (8 g) in anhydrous dichloromethane (250 ml) under an atmosphere of nitrogen. The reaction was left as such for 3 h. The reaction was washed with saturated bicarbonate solution (200 ml) and dried over sodium sulphate and concentrated in vacuo to yield an off white solid.
  • Step 5 Preparation of 1-acetyl-5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine]
  • Step 1 1-(2-chloropyridin-4-yl)carbonylspiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butyl ester
  • Step 2 preparation of 1-(2-chloropyridin-4-yl)carbonylspiro[indoline-3,4′-piperidine]trifluoroacetic acid salt
  • Trifluoroacetic acid (30 ml) was added to a solution of solution of 1-(2-chloropyridin-4-yl)carbonylspiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butyl ester (2.3 g) in anhydrous dichloromethane (50 ml), the solution darkening upon addition. The reaction was left as such for 15 min. The reaction mixture was evaporated in vacuo and the dark residue re-suspended in dry ether (100 ml). The residue was triturated until it became a free-flowing beige precipitate.
  • Step 3 Preparation of 1-(2-chloropyridin-4-yl)carbonyl-1′-[trans-3-phenylallyl]spiro[indoline-3,4′-piperidine]
  • Step 1 Preparation of 5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine]
  • Step 2 Preparation of 1-(pyridin-4-yl)carbonyl-5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine]
  • Step 1 Preparation of 8-[trans-3-(4-chlorophenyl)allyl]-1,4-dioxa-8-azaspiror4.5]decane
  • 1,4-Dioxa-8-azaspiro[4.5]decane (0.88 g) was dissolved in chloroform (5 ml) and diisopropylethylamine (2.1 ml) was added. A solution of 4-chlorocinnamyl chloride (1.2 g) dissolved in chloroform (2 ml) was added and mixture was heated to 70° C. overnight. The solvents were evaporated in vacuo and flash chromatography [SiO 2; ethyl acetate-hexane-triethylamine (50:50:2)] yielded 1.38 g (76%) of the desired ketal as a yellow oil.
  • Methoxymethyltriphenylphosphonium chloride (2.4 g) was dissolved in tetrahydrofuran (20 ml) and was cooled to 4° C. Potassium tert-butoxide (0.78 g) was added, turning the solution a bright orange colour. The reaction was left as such for 30 min. A solution of 1-[trans-3-(4-chlorophenyl)allyl]-4-oxopiperidine (0.85 g) dissolved in tetrahydrofuran (10 ml) was added and the mixture was stirred for 10 min. The solvents were evaporated in vacuo and the residue re-suspended in ether. The organics were washed with water and dried over anhydrous magnesium sulfate.
  • Step 4 Preparation of 5-methyl-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine]
  • Trifluoroacetic acid (0.75 ml) was added to a stirred solution of 1-[trans-3-(4-chlorophenyl)allyl]-4-methoxymethylenepiperidine-and 4-tolylhydrazine hydrochloride (28 mg) in chloroform (5 ml) and the reaction was heated to 50° C. for 5 h.
  • Triethylsilane (2 ml) was added and the reaction was heated at 50° C. for a further 5 h. The mixture was allowed to cool and was quenched in concentrated ammonia solution/ice chips (20 ml).
  • Step 5 Preparation of 1-(4-cyanobenzoyl)-5-methyl-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine]
  • This step was achieved using a Zymark XP2 synthetic chemistry robot.
  • a solution of 5-methyl-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine] (2 ml of a solution derived from dissolving 1.43 g in 100 ml of THF) was added to a robot tube and the solvent was removed in vacuo.
  • 4-Cyanobenzoic acid 28 mg was weighed into a different robot tube.
  • Compounds XXIX-201, I-282, I-232 were prepared according to standard procedures analogous to those described in Example 7.
  • Compound XXV-222 was prepared by treating compound XXIX-201 with potassium carbonate in methanol.
  • Compound I-222 was prepared by re-acylation of compound XXV-222 under standard conditions.
  • Step 1 Preparation of (E)-3-(4-trifluoromethyl-phenyl)-acrylic acid ethyl ester
  • step 1 To a solution of the ester obtained in step 1 (37.1 g) in toluene (310 ml) at 0° C. was added dropwise diisobutylaluminium hydride (1.2M in toluene, 317 ml) and the solution was stirred at 0° C. for 1 h. Water (47.6 ml) was carefully added at 0° C. followed by sodium hydroxide 2M (47.6 ml) and finally water (95.1 ml). The mixture was allowed to stir at room temperature for 1 h.
  • diisobutylaluminium hydride 1.2M in toluene, 317 ml
  • step 2 To a solution of the alcohol obtained in step 2 (10 g) in dimethylacetamide (100 ml) at room temperature were added triphenylphosphine (23 g) and carbon tetrabromide (29 g). The resulting solution was stirred at room temperature for 1 h, poured into water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate and filtered over silica gel to give 13 g of the desired product as a white solid (95%) which was characterized by its mass and NMR spectra.
  • Step 4 Preparation of 1-(2-chloropyridin-4-yl)carbonyl-5-chloro-1′-[(E)-3-(4-trifluoromethyl-phenyl)allyl]spiro[indolin-3,4′-piperidine]
  • Step 1 Preparation of (Z)-3-(4-chloro-phenyl)-2-fluoro-acrylic acid methyl ester
  • 4-Chlorobenzaldehyde (0.66 g) was added to a suspension of diethylfluorooxalacetate, sodium salt (1 g, prepared from diethyl oxalate, ethylfluoroacetate and sodium hydride according to Alberg et al. J. Am. Chem. Soc. 1992, 3542) in tetrahydrofuran (20 ml) at 0° C., and the resulting: mixture was stirred 1 h at 0° C. then 3 h at 80° C.
  • reaction mixture was concentrated in vacuo, diluted with diethyl ether, washed with aqueous sodium bicarbonate, water and brine, dried over sodium sulfate and concentrated in vacuo to afford a crude residue (1.2 g) which was used diretly in the next step.
  • Step 4 Preparation of 1-(2-chloropyridin-4-yl)carbonyl-5-chloro-1′-[(Z)-3-(4-chlorophenyl)-2-fluoro-allyl]spiro[indolin-3,4′-piperidine]
  • Step 2 to 4 were carried out following the procedure described in Example 8, step 2-4 to give 0.17 g of the desired product (41%) which was characterized by its mass and NMR spectra. MS (ES+) 530.
  • Step 3 Preparation of 1-(2-chloropyridin-4-yl)carbonyl-5-chloro-1′-[trans-3-(4-methoxy-phenyl)allyl]spiro[indolin-3,4′-piperidine]
  • Step 1 Preparation of (Z)-3-chloro-3-(4-chloro-phenyl)-acrylic acid methyl ester
  • step 2 (Z)-3-chloro-3-(4-chloro-phenyl)-acrylic acid methyl ester ( 462 mg) was converted into the desired product (391 mg, 96%) which was characterized by its mass and NMR spectra.
  • Step 4 Preparation of 1-(2-chloropyridin-4-yl)carbonyl-5-chloro-1′-[(Z)-3-(4-chlorophenyl)-3-chloro-allyl]spiro[indolin-3,4′-piperidine]
  • Step 1 Preparation of (Z)-3-(4-Chloro-phenyl)-3-fluoro-acrylic acid methyl ester
  • Step 4 Preparation of 1-(2-chloropyridin-4-yl)carbonyl-5-chloro-1′-[(Z)-3-(4-chlorophenyl)-3-fluoro-allyl]spiro[indolin-3,4′-piperidine]
  • Step 2 to 4 were carried out following the procedure described in Example 11, step 2-4 to give 163 mg of the desired product (42%) which was characterized by its mass and NMR spectra. MS (ES+) 531.
  • Step 1 Preparation of Compound XXX-121. 1-nitroso-5-fluoro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine]
  • Step 2 Preparation of 1-amino-5-fluoro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine]
  • Step 3 Preparation of 1-carboxylic acid (4-chloro-phenyl)-amide-5-fluoro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine]
  • Standard wash will refer to the following washing sequence: dimethylformamide, dichloromethane, dimethylformamide, dichloromethane, methanol, dichloromethane, methanol (X2), tert-butyl methyl ether (X2) and resin swelling protocol will be based on a standard of 10 ml of solvent per gram of resin.
  • Compound identities and purities were determined using High Performance Liquid Chromatography lo coupled Mass Spectrometry (HPLC-MS) and Proton Nuclear Magnetic Resonance (1H NMR) on selected compounds.
  • REM resin was prepared from commercially available (hydroxymethyl)polystyrene resin and acryloyl chloride. The loading of the resins were assumed to be constant at 1.2 mmolg ⁇ 1 throughout the synthesis.
  • Step A Loading of 4-Formylpiperidine dimethyl acetal onto REM resin (Resin A)
  • Step D Preparation of Solid supported 1,2-Dihydro-spiro[3H-indole-3,4′-piperidine] (Resin D)
  • Step E Preparation of Solid supported 1,2-Dihydro-1-(4-nitrobenzoyl)-spiro[3H-indole-3,4′-piperidine] (Resin E)
  • Resin D (0.5 g, 0.6 mmol) was swollen in anhydrous dichloromethane (5 ml). To the mixture was added 4-nitrobenzoyl chloride (0.33 g, 1.8 mmol) and N,N-diisopropylethylamine (0.42 ml, 2.4 mmol). After shaking at room temperature for 18 hours, the resin was filtered, washed according to the standard wash cycle and dried in vacuo to afford 0.53 g of the desired resin E.
  • Step F Quaternization of Solid supported 1,2-Dihydro-1-(4-nitrobenzoyl)-spiro[3H-indole-3,4′-piperidine] (Resin F)
  • Step G Preparation of 1,2-Dihydro-1-(4-nitrobenzoyl)-1′-(3-phenyl-2-propenyl)-spiro[3H-indole-3,4′-piperidine]
  • This Example illustrates the pesticidal/insecticidal properties of compounds of formula (I).
  • Cotton leaf discs were placed on agar in a 24-well microtiter plate and sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs were infested with 5 L 1 larvae. The samples were checked for mortality, repellent effect, feeding behaviour, and growth regulation 3 days after treatment (DAT).
  • Eggs (0-24 h old) were placed in 24-well microtiter plate on artificial diet and treated with test solutions at an application rate of 200 ppm by pipetting. After an incubation period of 4 days, samples were checked for egg mortality, larval mortality, and growth regulation.
  • MTP microtiter plate
  • Bean leaf discs on agar in 24-well microtiter plates were sprayed with test solutions at an application rate of 200 ppm. After drying, the leaf discs are infested with mite populations of mixed ages. 8 days later, discs are checked for egg mortality, larval mortality, and adult mortality. The following compounds gave at least 80% control of Tetranychus urticae:
  • Aedes larvae (L2) together with a nutrition mixture are placed in 96-well microtiter plates. Test solutions at an application rate of 2ppm are pipetted into the wells. 2 days later, insects were checked for mortality and growth inhibition. The following compounds gave at least 80% control of Aedes aegypti

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Diabetes (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Endocrinology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
US10/517,957 2002-06-14 2003-06-04 Spiroindolinepiperidine derivatives Abandoned US20060106045A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/859,410 US9686990B2 (en) 2002-06-14 2015-09-21 Spiroindolinepiperidine derivatives

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB0213715.6A GB0213715D0 (en) 2002-06-14 2002-06-14 Chemical compounds
GB02137`5.6 2002-06-14
PCT/GB2003/002424 WO2003106457A1 (en) 2002-06-14 2003-06-04 Spiroindolinepiperidine derivatives

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2003/002424 A-371-Of-International WO2003106457A1 (en) 2002-06-14 2003-06-04 Spiroindolinepiperidine derivatives

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/234,793 Division US9174987B2 (en) 2002-06-14 2011-09-16 Spiroindolinepiperidine derivatives

Publications (1)

Publication Number Publication Date
US20060106045A1 true US20060106045A1 (en) 2006-05-18

Family

ID=9938602

Family Applications (3)

Application Number Title Priority Date Filing Date
US10/517,957 Abandoned US20060106045A1 (en) 2002-06-14 2003-06-04 Spiroindolinepiperidine derivatives
US13/234,793 Expired - Fee Related US9174987B2 (en) 2002-06-14 2011-09-16 Spiroindolinepiperidine derivatives
US14/859,410 Expired - Lifetime US9686990B2 (en) 2002-06-14 2015-09-21 Spiroindolinepiperidine derivatives

Family Applications After (2)

Application Number Title Priority Date Filing Date
US13/234,793 Expired - Fee Related US9174987B2 (en) 2002-06-14 2011-09-16 Spiroindolinepiperidine derivatives
US14/859,410 Expired - Lifetime US9686990B2 (en) 2002-06-14 2015-09-21 Spiroindolinepiperidine derivatives

Country Status (28)

Country Link
US (3) US20060106045A1 (el)
EP (2) EP1515969B2 (el)
JP (1) JP4837913B2 (el)
KR (1) KR101013428B1 (el)
CN (4) CN1944431A (el)
AP (1) AP1850A (el)
AR (1) AR040208A1 (el)
AT (1) ATE478870T1 (el)
AU (1) AU2003240071B2 (el)
BR (1) BR0312129B1 (el)
CA (1) CA2487494C (el)
CO (1) CO5621237A2 (el)
CY (1) CY1111822T1 (el)
DE (1) DE60333919D1 (el)
DK (1) DK1515969T3 (el)
EA (1) EA014223B1 (el)
ES (1) ES2351188T3 (el)
GB (1) GB0213715D0 (el)
IL (3) IL165226A0 (el)
MA (1) MA27365A1 (el)
MX (1) MXPA04012349A (el)
NZ (1) NZ536734A (el)
PT (1) PT1515969E (el)
SI (1) SI1515969T1 (el)
TW (1) TWI343784B (el)
UA (1) UA81767C2 (el)
WO (1) WO2003106457A1 (el)
ZA (1) ZA200410058B (el)

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050288317A1 (en) * 2004-06-24 2005-12-29 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20050288338A1 (en) * 2004-06-24 2005-12-29 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20050288329A1 (en) * 2004-06-24 2005-12-29 Wenqing Yao 2-Methylprop anamides and their use as pharmaceuticals
US20060004049A1 (en) * 2004-06-24 2006-01-05 Wenqing Yao N-substituted piperidines and their use as pharrmaceuticals
US20060009471A1 (en) * 2004-06-24 2006-01-12 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20060009491A1 (en) * 2004-06-24 2006-01-12 Incyte Corporation Amido compounds and their use as pharmaceuticals
US20060116382A1 (en) * 2004-11-10 2006-06-01 Wenqing Yao Lactam compounds and their use as pharmaceuticals
US20060122210A1 (en) * 2004-11-18 2006-06-08 Wenqing Yao Inhibitors of 11-beta hydroxyl steroid dehydrogenase type I and methods of using the same
US20060122197A1 (en) * 2004-08-10 2006-06-08 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20060270653A1 (en) * 2004-11-29 2006-11-30 Ioana Drutu Modulators of muscarinic receptors
US20070066584A1 (en) * 2005-09-21 2007-03-22 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20070129345A1 (en) * 2005-12-05 2007-06-07 Jincong Zhuo Lactam compounds and methods of using the same
US20070197506A1 (en) * 2006-01-12 2007-08-23 Wenqing Yao Modulators of 11-beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same
US20070197530A1 (en) * 2006-01-31 2007-08-23 Yun-Long Li Amido compounds and their use as pharmaceuticals
US20070208001A1 (en) * 2006-03-03 2007-09-06 Jincong Zhuo Modulators of 11- beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same
US20070213311A1 (en) * 2006-03-02 2007-09-13 Yun-Long Li Modulators of 11-beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same
US20070213315A1 (en) * 2006-02-22 2007-09-13 Robert Davies Modulators of muscarinic receptors
US20070270424A1 (en) * 2006-05-17 2007-11-22 Yun-Long Li Heterocyclic inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1 and methods of using the same
US20070293529A1 (en) * 2006-05-01 2007-12-20 Yun-Long Li Tetrasubstituted ureas as modulators of 11-beta hydroxyl steroid dehydrogenase type 1
US20080015179A1 (en) * 2005-12-22 2008-01-17 Makings Lewis R Modulators of muscarinic receptors
US20080047479A1 (en) * 1997-10-27 2008-02-28 Correct Craft, Inc. Water Sport Towing Apparatus and Method
US20080318991A1 (en) * 2007-06-21 2008-12-25 Incyte Corporation Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1
US20090099222A1 (en) * 2007-10-03 2009-04-16 Davies Robert J Modulators of muscarinic receptors
US20090291946A1 (en) * 2004-11-10 2009-11-26 Incyte Corporation Lactam compounds and their use as pharmaceuticals
US7786107B2 (en) 2006-08-18 2010-08-31 Vertex Pharmaceuticals Incorporated Modulators of muscarinic receptors
US7786141B2 (en) 2004-08-19 2010-08-31 Vertex Pharmaceuticals Incorporated Dihydrospiroindene modulators of muscarinic receptors
US20100311720A1 (en) * 2004-08-19 2010-12-09 Vertex Pharmaceuticals Incorporated Spiroindoline Modulators of Muscarinic Receptors

Families Citing this family (359)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0213715D0 (en) * 2002-06-14 2002-07-24 Syngenta Ltd Chemical compounds
GB0328908D0 (en) 2003-12-12 2004-01-14 Syngenta Participations Ag Chemical compounds
GB0328905D0 (en) * 2003-12-12 2004-01-14 Syngenta Participations Ag Chemical compounds
GB0328907D0 (en) * 2003-12-12 2004-01-14 Syngenta Participations Ag Chemical compounds
EP1716148A2 (en) 2003-12-23 2006-11-02 Arena Pharmaceuticals, Inc. Novel spiroindoline or spiroisoquinoline compounds, methods of use and compositions thereof
AR053710A1 (es) 2005-04-11 2007-05-16 Xenon Pharmaceuticals Inc Compuestos espiroheterociclicos y sus usos como agentes terapeuticos
MY158766A (en) 2005-04-11 2016-11-15 Xenon Pharmaceuticals Inc Spiro-oxindole compounds and their uses as therapeutic agents
GB0601402D0 (en) 2006-01-24 2006-03-08 Syngenta Participations Ag Chemical Compounds
CA2651681A1 (en) * 2006-05-18 2007-11-29 Merck & Co., Inc. Aryl-fused spirocyclic compounds
JP5460324B2 (ja) 2006-10-12 2014-04-02 ゼノン・ファーマシューティカルズ・インコーポレイテッド 治療剤としてのスピロ−オキシインドール化合物の使用
RU2011119626A (ru) 2008-10-17 2012-11-27 Ксенон Фармасьютикалз Инк. Спирооксиндольные соединения и их применение в качестве терапевтичеких средств
CA2741024A1 (en) 2008-10-17 2010-04-22 Xenon Pharmaceuticals Inc. Spiro-oxindole compounds and their use as therapeutic agents
AP2653A (en) * 2008-12-12 2013-04-25 Syngenta Participations Ag Spiroheterocyclic N-oxypiperidines as pesticides
AR077252A1 (es) 2009-06-29 2011-08-10 Xenon Pharmaceuticals Inc Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos
MY165579A (en) 2009-10-14 2018-04-05 Xenon Pharmaceuticals Inc Synthetic methods for spiro-oxindole compounds
AU2011212478B2 (en) * 2010-02-05 2014-11-06 Intervet International B.V. Spiroindoline Compounds For Use as Anthelminthics
US9504671B2 (en) 2010-02-26 2016-11-29 Xenon Pharmaceuticals Inc. Pharmaceutical compositions of spiro-oxindole compound for topical administration and their use as therapeutic agents
WO2011107504A1 (de) 2010-03-04 2011-09-09 Bayer Cropscience Ag Fluoralkyl- substituierte 2 -amidobenzimidazole und deren verwendung zur steigerung der stresstoleranz in pflanzen
WO2011138285A1 (de) 2010-05-05 2011-11-10 Bayer Cropscience Ag Thiazolderivate als schädlingsbekämpfungsmittel
MX341267B (es) 2010-06-18 2016-08-09 Bayer Ip Gmbh Combinaciones de principios activos con propiedades insecticidas y acaricidas.
KR20130088138A (ko) 2010-06-28 2013-08-07 바이엘 인텔렉쳐 프로퍼티 게엠베하 농약으로서 사용하기 위한 헤테로아릴-치환된 피리딘 화합물
JP2012017289A (ja) 2010-07-08 2012-01-26 Bayer Cropscience Ag 殺虫性ピロリン誘導体
WO2012004293A2 (de) 2010-07-08 2012-01-12 Bayer Cropscience Ag Insektizide und fungizide wirkstoffkombinationen
JP2012062267A (ja) 2010-09-15 2012-03-29 Bayer Cropscience Ag 殺虫性ピロリンｎ−オキサイド誘導体
JP2012082186A (ja) 2010-09-15 2012-04-26 Bayer Cropscience Ag 殺虫性アリールピロリジン類
WO2012045680A2 (de) 2010-10-04 2012-04-12 Bayer Cropscience Ag Insektizide und fungizide wirkstoffkombinationen
WO2012052490A1 (en) 2010-10-21 2012-04-26 Bayer Cropscience Ag N-benzyl heterocyclic carboxamides
KR20130116074A (ko) 2010-11-02 2013-10-22 바이엘 인텔렉쳐 프로퍼티 게엠베하 Ｎ-헤타릴메틸 피라졸릴카르복사미드
CN103313971B (zh) 2010-11-15 2015-12-02 拜耳知识产权有限责任公司 N-芳基吡唑（硫代）甲酰胺
EP2646413A1 (de) 2010-11-29 2013-10-09 Bayer Intellectual Property GmbH Alpha-beta-ungesättigte imine
AP3519A (en) 2010-12-01 2016-01-11 Bayer Ip Gmbh Use of fluopyram for controlling nematodes in crops and for increasing yield
TWI667347B (zh) 2010-12-15 2019-08-01 瑞士商先正達合夥公司 大豆品種ｓｙｈｔ０ｈ２及偵測其之組合物及方法
EP2471363A1 (de) 2010-12-30 2012-07-04 Bayer CropScience AG Verwendung von Aryl-, Heteroaryl- und Benzylsulfonamidocarbonsäuren, -carbonsäureestern, -carbonsäureamiden und -carbonitrilen oder deren Salze zur Steigerung der Stresstoleranz in Pflanzen
US8946124B2 (en) 2011-02-17 2015-02-03 Bayer Intellectual Property Gmbh Substituted 3-(biphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-ones for therapy and halogen-substituted spirocyclic ketoenols
CA2827304C (en) 2011-02-17 2018-11-13 Bayer Intellectual Property Gmbh Use of sdhi fungicides on conventionally bred asr-tolerant, stem canker resistant and/or frog-eye leaf spot resistant soybean varieties
US9204640B2 (en) 2011-03-01 2015-12-08 Bayer Intellectual Property Gmbh 2-acyloxy-pyrrolin-4-ones
AR085509A1 (es) 2011-03-09 2013-10-09 Bayer Cropscience Ag Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas
WO2012120105A1 (en) 2011-03-10 2012-09-13 Bayer Cropscience Ag Use of lipochito-oligosaccharide compounds for safeguarding seed safety of treated seeds
DK2686303T3 (en) 2011-03-18 2016-03-29 Bayer Ip Gmbh N- (3-carbamoylphenyl) -1 H -pyrazole-5-carboxamide derivatives and their use for controlling animal pests
AR090010A1 (es) 2011-04-15 2014-10-15 Bayer Cropscience Ag 5-(ciclohex-2-en-1-il)-penta-2,4-dienos y 5-(ciclohex-2-en-1-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas, usos y metodos de tratamiento
AR085568A1 (es) 2011-04-15 2013-10-09 Bayer Cropscience Ag 5-(biciclo[4.1.0]hept-3-en-2-il)-penta-2,4-dienos y 5-(biciclo[4.1.0]hept-3-en-2-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas
AR085585A1 (es) 2011-04-15 2013-10-09 Bayer Cropscience Ag Vinil- y alquinilciclohexanoles sustituidos como principios activos contra estres abiotico de plantas
CN102246775B (zh) * 2011-05-17 2013-05-29 德强生物股份有限公司 一种杀虫增效组合物
EP2535334A1 (de) 2011-06-17 2012-12-19 Bayer CropScience AG Kristalline Modifikationen von Penflufen
EP2540163A1 (en) 2011-06-30 2013-01-02 Bayer CropScience AG Nematocide N-cyclopropyl-sulfonylamide derivatives
CN103957711A (zh) 2011-07-04 2014-07-30 拜耳知识产权有限责任公司 取代的异喹啉酮、异喹啉二酮、异喹啉三酮和二氢异喹啉酮或其各自的盐作为活性剂对抗植物非生物胁迫的用途
EP2736327B1 (de) 2011-07-26 2018-02-21 Clariant International Ltd Veretherte laktatester, verfahren zu ihrer herstellung und ihre verwendung zur verbesserung der wirkung von pflanzenschutzmitteln
UA115128C2 (uk) 2011-07-27 2017-09-25 Байєр Інтеллектуал Проперті Гмбх Протравлювання насіння для боротьби з фітопатогенними грибами
US9096599B2 (en) 2011-08-04 2015-08-04 Intervet Inc. Spiroindoline compounds
EP2561759A1 (en) 2011-08-26 2013-02-27 Bayer Cropscience AG Fluoroalkyl-substituted 2-amidobenzimidazoles and their effect on plant growth
JP6138797B2 (ja) 2011-09-16 2017-05-31 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ 植物収量を向上させるためのアシルスルホンアミド類の使用
IN2014CN01860A (el) 2011-09-16 2015-05-29 Bayer Ip Gmbh
BR112014006208B1 (pt) 2011-09-16 2018-10-23 Bayer Intellectual Property Gmbh método de indução de respostas reguladoras do crescimento nas plantas aumentando o rendimento de plantas úteis ou plantas de cultura e composição de aumento do rendimento da planta compreendendo isoxadifen-etilo ou isoxadifeno e combinação de fungicidas
JP2013082632A (ja) 2011-10-05 2013-05-09 Bayer Cropscience Ag 農薬製剤及びその製造方法
EP2604118A1 (en) 2011-12-15 2013-06-19 Bayer CropScience AG Active ingredient combinations having insecticidal and acaricidal properties
US9414595B2 (en) 2011-12-19 2016-08-16 Bayer Cropscience Ag Use of anthranilic acid diamide derivatives for pest control in transgenic crops
JP6062958B2 (ja) 2011-12-20 2017-01-18 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ 新規殺虫性芳香族アミド類
EP2606726A1 (de) 2011-12-21 2013-06-26 Bayer CropScience AG N-Arylamidine-substituierte trifluoroethylsulfid-Derivate als Akarizide und Insektizide
UA117905C2 (uk) 2012-01-21 2018-10-25 Байєр Інтеллектуал Проперті Гмбх Застосування стимулятора імунного захисту для боротьби зі шкідливими бактеріальними організмами на культурних рослинах
CN104321317B (zh) 2012-03-14 2016-09-21 拜耳知识产权有限责任公司 杀虫的芳基吡咯烷
AU2013261868B2 (en) 2012-05-16 2016-05-26 Discovery Purchaser Corporation Insecticidal water-in-oil (W/O) formulation
IN2014DN08358A (el) 2012-05-16 2015-05-08 Bayer Cropscience Ag
AR091104A1 (es) 2012-05-22 2015-01-14 Bayer Cropscience Ag Combinaciones de compuestos activos que comprenden un derivado lipo-quitooligosacarido y un compuesto nematicida, insecticida o fungicida
KR102095979B1 (ko) 2012-05-30 2020-04-02 바이엘 크롭사이언스 악티엔게젤샤프트 생물학적 방제제 및 살곤충제를 포함하는 조성물
ES2599504T3 (es) 2012-05-30 2017-02-02 Clariant International Ltd Utilización de N-metil-N-acil-glucaminas como agentes solubilizantes
AU2013269661B2 (en) 2012-05-30 2016-10-27 Bayer Cropscience Ag Compositions comprising a biological control agent and an insecticide
CN104640965A (zh) 2012-05-30 2015-05-20 科莱恩金融(Bvi)有限公司 包含n-甲基-n-酰基葡糖胺的组合物
WO2014005982A1 (de) 2012-07-05 2014-01-09 Bayer Cropscience Ag Insektizide und fungizide wirkstoffkombinationen
ES2702303T3 (es) 2012-07-31 2019-02-28 Bayer Cropscience Ag Composiciones plaguicidas que comprenden una mezcla de terpeno y flupiradifurona
EP2885301A1 (de) 2012-08-17 2015-06-24 Bayer CropScience AG Azaindolcarbonsäure- und -thiocarbonsäureamide als insektizide und akarizide
WO2014037340A1 (de) 2012-09-05 2014-03-13 Bayer Cropscience Ag Verwendung substituierter 2-amidobenzimidazole, 2-amidobenzoxazole und 2-amidobenzothiazole oder deren salze als wirkstoffe gegen abiotischen pflanzenstress
CN105101800B (zh) 2012-10-02 2018-04-13 拜耳农作物科学股份公司 作为杀虫剂的杂环化合物
WO2014060381A1 (de) 2012-10-18 2014-04-24 Bayer Cropscience Ag Heterocyclische verbindungen als schädlingsbekämpfungsmittel
JP2016503395A (ja) 2012-10-31 2016-02-04 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 病害生物防除剤としての複素環化合物
DE102012021647A1 (de) 2012-11-03 2014-05-08 Clariant International Ltd. Wässrige Adjuvant-Zusammensetzungen
UA117816C2 (uk) 2012-11-06 2018-10-10 Байєр Кропсайєнс Акцієнгезелльшафт Гербіцидна комбінація для толерантних соєвих культур
MX2015006328A (es) 2012-11-30 2015-09-07 Bayer Cropscience Ag Mezcla fungicida o pesticida binaria.
CN104812247A (zh) 2012-11-30 2015-07-29 拜耳作物科学股份公司 二元杀真菌混合物
CN105025721A (zh) 2012-12-03 2015-11-04 拜耳作物科学股份公司 包含生物防治剂和杀虫剂的组合物
CN105025722A (zh) 2012-12-03 2015-11-04 拜耳作物科学股份公司 包含生物防治剂和杀虫剂的组合物
US20150305348A1 (en) 2012-12-03 2015-10-29 Bayer Cropscience Ag Composition comprising biological control agents
US9867377B2 (en) 2012-12-03 2018-01-16 Bayer Cropscience Ag Composition comprising a biological control agent and an insecticide
WO2014086753A2 (en) 2012-12-03 2014-06-12 Bayer Cropscience Ag Composition comprising biological control agents
US20150305334A1 (en) 2012-12-05 2015-10-29 Bayer Cropscience Ag Use of substituted 1-(aryl ethynyl)-, 1-(heteroaryl ethynyl)-, 1-(heterocyclyl ethynyl)- and 1-(cycloalkenyl ethynyl)-cyclohexanols as active agents against abiotic plant stress
WO2014090765A1 (en) 2012-12-12 2014-06-19 Bayer Cropscience Ag Use of 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-5-amino-3-trifluoromethyl)-1 h-1,2,4 tfia zole for controlling nematodes in nematode-resistant crops
AR093996A1 (es) 2012-12-18 2015-07-01 Bayer Cropscience Ag Combinaciones bactericidas y fungicidas binarias
BR112015018311B1 (pt) 2013-02-06 2021-01-05 Bayer Animal Health Gmbh compostos derivados de pirazol substituídos por halogêneo como agentes de controle de pragas, composição farmacêutica e uso dos mesmos, processo para a preparação de composições de proteção de colheitas e método para o controle de pragas
AU2014214705A1 (en) 2013-02-11 2015-08-06 Bayer Cropscience Lp Compositions comprising a streptomyces-based biological control agent and another biological control agent
EP2953466A1 (en) 2013-02-11 2015-12-16 Bayer Cropscience LP Compositions comprising gougerotin and an insecticide
US20160024108A1 (en) 2013-03-12 2016-01-28 Bayer Cropscience Aktiengesellschaft Use of dithiine-tetracarboximides for controlling bacterial harmful organisms in useful plants
AR095785A1 (es) * 2013-04-09 2015-11-11 Bayer Pharma AG Derivados de espiroindolina y composiciones farmacéutica de los mismos
EP2986117A1 (en) 2013-04-19 2016-02-24 Bayer CropScience Aktiengesellschaft Binary insecticidal or pesticidal mixture
US9549552B2 (en) 2013-04-19 2017-01-24 Bayer Cropscience Aktiengesellschaft Active compound combinations having insecticidal properties
EP3010889B1 (de) 2013-06-20 2018-10-03 Bayer CropScience Aktiengesellschaft Arylsulfid- und arylsulfoxid-derivate als akarizide und insektizide
BR112015031291A2 (pt) 2013-06-20 2017-07-25 Bayer Cropscience Ag derivados de sulfureto de arila e derivados de arilalquil sulfóxido como acaricidas e inseticidas
AR096816A1 (es) 2013-07-08 2016-02-03 Bayer Cropscience Ag Derivados de arilsulfuro y arilsulfóxido de seis miembros enlazados con c-n como agentes para combatir parásitos
WO2015055554A1 (de) 2013-10-14 2015-04-23 Bayer Cropscience Ag Wirkstoff für die saatgut- und bodenbehandlung
UY35772A (es) 2013-10-14 2015-05-29 Bayer Cropscience Ag Nuevos compuestos plaguicidas
JP6472444B2 (ja) 2013-10-23 2019-02-20 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 有害生物防除剤としての置換されているキノキサリン誘導体
AU2014370025B2 (en) * 2013-12-24 2017-08-17 Zoetis Services Llc Spiroindoline antiparasitic derivatives
MX2016008653A (es) 2014-01-03 2016-09-26 Bayer Animal Health Gmbh Nuevas pirazolil-heteroarilamidas como agentes plaguicidas.
WO2015107133A1 (de) 2014-01-20 2015-07-23 Bayer Cropscience Ag Chinolinderivate als insektizide und akarizide
DE202014008415U1 (de) 2014-02-19 2014-11-25 Clariant International Ltd. Wässrige Adjuvant-Zusammensetzung zur Wirkungssteigerung von Elektrolyt-Wirkstoffen
DE202014008418U1 (de) 2014-02-19 2014-11-14 Clariant International Ltd. Schaumarme agrochemische Zusammensetzungen
JP6434048B2 (ja) 2014-04-02 2018-12-05 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 農薬としてのヘテロ環式化合物
WO2015160620A1 (en) 2014-04-16 2015-10-22 Bayer Cropscience Lp Compositions comprising ningnanmycin and an insecticide
WO2015160618A1 (en) 2014-04-16 2015-10-22 Bayer Cropscience Lp Compositions comprising ningnanmycin and a biological control agent
DE102014005771A1 (de) 2014-04-23 2015-10-29 Clariant International Ltd. Verwendung von wässrigen driftreduzierenden Zusammensetzungen
AU2015257746B2 (en) 2014-05-08 2018-11-22 Bayer Cropscience Aktiengesellschaft Pyrazolopyridine sulfonamides as nematicides
WO2015185531A1 (de) 2014-06-05 2015-12-10 Bayer Cropscience Aktiengesellschaft Bicyclische verbindungen als schädlingsbekämpfungsmittel
WO2016001119A1 (de) 2014-07-01 2016-01-07 Bayer Cropscience Aktiengesellschaft Insektizide und fungizide wirkstoffkombinationen
EP3169674B1 (de) 2014-07-15 2021-01-20 Bayer Animal Health GmbH Aryl-triazolyl-pyridine als schädlingsbekämpfungsmittel
DE102014012022A1 (de) 2014-08-13 2016-02-18 Clariant International Ltd. Organische Ammoniumsalze von anionischen Pestiziden
WO2016055096A1 (en) 2014-10-07 2016-04-14 Bayer Cropscience Ag Method for treating rice seed
AR102942A1 (es) 2014-12-11 2017-04-05 Bayer Cropscience Ag Derivados de arilsulfuro y arilsulfóxido de cinco miembros c-n-conectados, como plaguicidas
DE102014018274A1 (de) 2014-12-12 2015-07-30 Clariant International Ltd. Zuckertenside und deren Verwendung in agrochemischen Zusammensetzungen
BR112017012978B1 (pt) 2014-12-19 2021-06-08 Clariant International Ltd composição adjuvante aquosa compreendendo sulfato de polialquileno glicol éter, composição compreendendo alquilglucamidas e os usos das mesmas
CN107105674B (zh) 2014-12-22 2020-10-02 拜耳作物科学有限合伙公司 使用枯草芽孢杆菌或短小芽孢杆菌菌株治疗或预防凤梨病的方法
EP3081085A1 (en) 2015-04-14 2016-10-19 Bayer CropScience AG Method for improving earliness in cotton
TW201636017A (zh) 2015-02-05 2016-10-16 梯瓦製藥國際有限責任公司 以螺吲哚酮化合物之局部調配物治療帶狀疱疹後遺神經痛之方法
UY36548A (es) 2015-02-05 2016-06-01 Bayer Cropscience Ag Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas
UY36547A (es) 2015-02-05 2016-06-01 Bayer Cropscience Ag Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas
TWI702212B (zh) 2015-02-09 2020-08-21 德商拜耳作物科學股份有限公司 作為除害劑之經取代的２－硫基咪唑基羧醯胺類
BR112017019266B1 (pt) 2015-03-10 2022-05-10 Bayer Animal Health Gmbh Compostos derivados de pirazolila e composição farmacêutica compreendendo o referido composto
JP6730309B2 (ja) 2015-04-08 2020-07-29 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 有害生物防除剤としての縮合二環式ヘテロ環誘導体及び中間体生成物
WO2016174049A1 (en) 2015-04-30 2016-11-03 Bayer Animal Health Gmbh Anti-parasitic combinations including halogen-substituted compounds
EP2910126A1 (en) 2015-05-05 2015-08-26 Bayer CropScience AG Active compound combinations having insecticidal properties
KR20180005244A (ko) 2015-05-13 2018-01-15 바이엘 크롭사이언스 악티엔게젤샤프트 살충성 아릴피롤리딘, 그의 제조 방법 및 동물 해충 방제제로서의 그의 용도
RU2724555C2 (ru) 2015-07-06 2020-06-23 Байер Кропсайенс Акциенгезельшафт Гетероциклические соединения в качестве пестицидов
AU2016307233B2 (en) 2015-08-07 2020-12-24 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted condensed heterocyclic derivatives as pest control agents
DE202015008045U1 (de) 2015-10-09 2015-12-09 Clariant International Ltd. Universelle Pigmentdispersionen auf Basis von N-Alkylglukaminen
DE102015219651A1 (de) 2015-10-09 2017-04-13 Clariant International Ltd. Zusammensetzungen enthaltend Zuckeramin und Fettsäure
AU2016347345B2 (en) 2015-10-26 2020-06-25 Bayer Cropscience Aktiengesellschaft Condensed bicyclic heterocycle derivatives as pest control agents
WO2017093180A1 (de) 2015-12-01 2017-06-08 Bayer Cropscience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
EP3383874A1 (de) 2015-12-03 2018-10-10 Bayer CropScience Aktiengesellschaft Mesolonische halogenierte 3-(acetyl)-1-[(1,3-thiazol-5-yl)methyl]-1h-imidazo[1,2-a]pyridin-4-ium-2-olat derivate und verwandte verbindungen als insektizide
EP3414236A1 (de) 2016-02-11 2018-12-19 Bayer CropScience Aktiengesellschaft Substituierte 2-(het)aryl-imidazolyl-carboxyamide als schädlingsbekämpfungsmittel
KR20180107142A (ko) 2016-02-11 2018-10-01 바이엘 크롭사이언스 악티엔게젤샤프트 해충 방제제로서의 치환된 2-옥시이미다졸릴-카르복스아미드
WO2017144341A1 (de) 2016-02-23 2017-08-31 Bayer Cropscience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
EP3210468A1 (de) 2016-02-26 2017-08-30 Bayer CropScience Aktiengesellschaft Lösungsmittelfreie formulierungen von niedrig schmelzenden wirkstoffen
MX2018011214A (es) 2016-03-15 2019-03-28 Bayer Cropscience Ag Sulfonamidas sustituidas para controlar plagas animales.
EP3429997A1 (de) 2016-03-16 2019-01-23 Bayer CropScience Aktiengesellschaft N-(cyanbenzyl)-6-(cyclopropylcarbonylamino)-4-(phenyl)-pyridin-2-carboxamid-derivate und verwandte verbindungen als pestizide pflanzenschutzmittel
WO2017174414A1 (de) 2016-04-05 2017-10-12 Bayer Cropscience Aktiengesellschaft Naphthalin-derivate als schädlingsbekämpfungsmittel
ES2953467T3 (es) 2016-04-15 2023-11-13 Elanco Animal Health Gmbh Derivados de pirazolopirimidina
CN109068649A (zh) 2016-04-24 2018-12-21 拜耳农作物科学股份公司 氟吡菌酰胺和/或枯草芽孢杆菌用于防治芭蕉科植物的枯萎病的用途
BR112018071951A2 (pt) 2016-04-25 2019-02-05 Bayer Cropscience Ag 2-alquilimidazolilcarboxamidas substituídas como pesticidas
EP3241830A1 (de) 2016-05-04 2017-11-08 Bayer CropScience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
DE102016207877A1 (de) 2016-05-09 2017-11-09 Clariant International Ltd Stabilisatoren für Silikatfarben
WO2017198450A1 (en) 2016-05-15 2017-11-23 Bayer Cropscience Nv Method for increasing yield in maize
EP3245865A1 (en) 2016-05-17 2017-11-22 Bayer CropScience Aktiengesellschaft Method for increasing yield in brassicaceae
WO2017198449A1 (en) 2016-05-15 2017-11-23 Bayer Cropscience Nv Method for increasing yield in brassicaceae
WO2017198453A1 (en) 2016-05-16 2017-11-23 Bayer Cropscience Nv Method for increasing yield in potato, tomato or alfalfa
WO2017198452A1 (en) 2016-05-16 2017-11-23 Bayer Cropscience Nv Method for increasing yield in soybean
WO2017198455A2 (en) 2016-05-17 2017-11-23 Bayer Cropscience Nv Method for increasing yield in beta spp. plants
WO2017198451A1 (en) 2016-05-17 2017-11-23 Bayer Cropscience Nv Method for increasing yield in small grain cereals such as wheat and rice
WO2017198454A1 (en) 2016-05-17 2017-11-23 Bayer Cropscience Nv Method for increasing yield in cotton
US10750750B2 (en) 2016-07-11 2020-08-25 Covestro Llc Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds
US10653136B2 (en) 2016-07-11 2020-05-19 Covestro Llc Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds
US10653135B2 (en) 2016-07-11 2020-05-19 Covestro Llc Methods for treating seeds with an aqueous composition and seeds treated therewith
KR20190028763A (ko) 2016-07-12 2019-03-19 바이엘 크롭사이언스 악티엔게젤샤프트 해충 방제제로서의 바이시클릭 화합물
KR102435080B1 (ko) 2016-07-19 2022-08-22 바이엘 크롭사이언스 악티엔게젤샤프트 해충 방제제로서의 축합 바이시클릭 헤테로사이클 유도체
WO2018019676A1 (en) 2016-07-29 2018-02-01 Bayer Cropscience Aktiengesellschaft Active compound combinations and methods to protect the propagation material of plants
US11178877B2 (en) 2016-07-29 2021-11-23 Bayer Cropscience Aktiengesellschaft Formulation comprising a beneficial P. bilaii strain and talc for use in seed treatment
CA3033226A1 (en) 2016-08-10 2018-02-15 Bayer Cropscience Aktiengesellschaft Substituted 2-heterocyclyl imidazolyl-carboxamides as pest control agents
MA45918A (fr) 2016-08-15 2019-06-19 Bayer Ag Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
CN109963860A (zh) 2016-09-19 2019-07-02 拜耳作物科学股份公司 吡唑并[1,5-a]吡啶衍生物及其作为农药的用途
CN110062756B (zh) 2016-10-06 2022-09-02 拜耳作物科学股份公司 作为害虫防治剂的2-(杂)芳基取代的稠合双环杂环衍生物
WO2018065288A1 (de) 2016-10-07 2018-04-12 Bayer Cropscience Aktiengesellschaft 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz
EP3525588B1 (en) 2016-10-14 2024-04-24 PI Industries Ltd 4-substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms
JP2019532107A (ja) 2016-10-14 2019-11-07 ピーアイ インダストリーズ リミテッドＰｉ Ｉｎｄｕｓｔｒｉｅｓ Ｌｔｄ 望ましくない植物病原性微生物と戦うことで作物を保護するための４−アミノ置換フェニルアミジン誘導体およびその使用
TW201822637A (zh) 2016-11-07 2018-07-01 德商拜耳廠股份有限公司 用於控制動物害蟲的經取代磺醯胺類
KR102595730B1 (ko) 2016-11-11 2023-10-27 바이엘 애니멀 헬스 게엠베하 새로운 구충 퀴놀린-3-카르복스아미드 유도체
ES2837396T3 (es) 2016-11-23 2021-06-30 Bayer Cropscience Ag Derivados de 2-[3-(alquilsulfonil)-2H-indazol-2-il]-3H-imidazo[4,5-b]piridina y compuestos similares como pesticidas
EP3400801A1 (en) 2017-05-10 2018-11-14 Bayer CropScience Aktiengesellschaft Plant health effect of purpureocillium lilacinum
KR20190093648A (ko) 2016-12-16 2019-08-09 바이엘 악티엔게젤샤프트 살곤충제로서 사용하기 위한 메소이온성 이미다조피리딘
CN110382493A (zh) 2016-12-16 2019-10-25 拜耳农作物科学股份公司 作为农药的噻二唑衍生物
WO2018116072A1 (en) 2016-12-20 2018-06-28 Pi Industries Ltd. Heterocyclic compounds
AU2018208422B2 (en) 2017-01-10 2021-11-11 Bayer Aktiengesellschaft Heterocyclene derivatives as pest control agents
KR102515694B1 (ko) 2017-01-10 2023-03-29 바이엘 악티엔게젤샤프트 해충 방제제로서의 헤테로사이클 유도체
WO2018138050A1 (de) 2017-01-26 2018-08-02 Bayer Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
TW201833107A (zh) 2017-02-06 2018-09-16 德商拜耳廠股份有限公司 作為殺蟲劑之經２－（雜）芳基取代的稠合雜環衍生物
EP3369320A1 (de) 2017-03-02 2018-09-05 Bayer CropScience Aktiengesellschaft Wirkstoff zur bekämpfung von wanzen
WO2018177993A1 (de) 2017-03-31 2018-10-04 Bayer Cropscience Aktiengesellschaft Pyrazole zur bekämpfung von arthropoden
AU2018241748B2 (en) 2017-03-31 2023-02-09 Elanco Animal Health Gmbh Tricyclic carboxamides for controlling arthropods
JP2020516630A (ja) 2017-04-12 2020-06-11 バイエル・アクチエンゲゼルシヤフト 殺虫剤として使用するためのメソイオン性イミダゾピリジン類
CN110678442A (zh) 2017-04-20 2020-01-10 Pi工业有限公司 新型苯胺化合物
KR20190141194A (ko) 2017-04-21 2019-12-23 바이엘 악티엔게젤샤프트 살곤충제로서의 메소이온성 이미다조피리딘
ES2923376T3 (es) 2017-04-24 2022-09-27 Bayer Ag Derivados de heterociclos bicíclicos fusionados como plaguicidas
AU2018257582B2 (en) 2017-04-27 2022-06-16 Bayer Animal Health Gmbh New bicyclic pyrazole derivatives
TWI782983B (zh) 2017-04-27 2022-11-11 德商拜耳廠股份有限公司 雜芳基苯基胺基喹啉及類似物
US11089783B2 (en) 2017-05-02 2021-08-17 Bayer Aktiengesellschaft 2-(het)aryl-substituted fused heterocycle derivatives as pesticides
BR112019022831A2 (pt) 2017-05-02 2020-05-26 Bayer Aktiengesellschaft Derivados heterocíclicos bicíclicos condensados substituídos por 2-(het)arila como agentes de controle de praga
JP2020518589A (ja) 2017-05-03 2020-06-25 バイエル・アクチエンゲゼルシヤフト トリ置換シリルベンジルベンゾイミダゾール類及び類縁体
JP2020519575A (ja) 2017-05-03 2020-07-02 バイエル・アクチエンゲゼルシヤフト トリ置換シリルメチルフェノキシキノリン類及び類縁体
CN110650628A (zh) 2017-05-03 2020-01-03 拜耳公司 三取代的甲硅烷基杂芳氧基喹啉及其类似物
WO2018202525A1 (en) 2017-05-04 2018-11-08 Bayer Cropscience Aktiengesellschaft Phenoxyethanamine derivatives for controlling pests
PL3619196T3 (pl) 2017-05-04 2022-08-29 Bayer Cropscience Aktiengesellschaft Pochodne 2-{[2-(fenyloksymetylo)pirydyn-5-yl]oksy}-etanoaminy i związki pokrewne jako środki do zwalczania szkodników np. do ochrony upraw
MX2019015895A (es) 2017-06-30 2020-02-07 Bayer Animal Health Gmbh Nuevos derivados de azaquinolina.
WO2019007891A1 (de) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insektizide wirkstoffkombinationen
WO2019007888A1 (de) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insektizide wirkstoffkombinationen
WO2019007887A1 (de) 2017-07-06 2019-01-10 Bayer Aktiengesellschaft Insektizide und fungizide wirkstoffkombinationen
EP3284739A1 (de) 2017-07-19 2018-02-21 Bayer CropScience Aktiengesellschaft Substituierte (het)arylverbindungen als schädlingsbekämpfungsmittel
WO2019025341A1 (en) 2017-08-04 2019-02-07 Bayer Animal Health Gmbh QUINOLINE DERIVATIVES FOR THE TREATMENT OF INFECTIONS BY HELMINTHES
WO2019035881A1 (en) 2017-08-17 2019-02-21 Bayer Cropscience Lp DISPERSIBLE COMPOSITIONS IN LIQUID FERTILIZER AND ASSOCIATED METHODS
US11655258B2 (en) 2017-08-22 2023-05-23 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
JP7277445B2 (ja) 2017-09-20 2023-05-19 三井化学クロップ＆ライフソリューション株式会社 動物用外部寄生虫長期防除剤
KR102622644B1 (ko) 2017-10-04 2024-01-10 바이엘 악티엔게젤샤프트 해충 방제제로서의 헤테로시클릭 화합물의 유도체
EP3473103A1 (de) 2017-10-17 2019-04-24 Bayer AG Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinon
EP3473100A1 (en) 2017-10-18 2019-04-24 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
CN111246742B (zh) 2017-10-18 2022-09-23 拜耳公司 具有杀虫/杀螨特性的活性化合物结合物
TWI788432B (zh) 2017-10-18 2023-01-01 德商拜耳廠股份有限公司 具有殺昆蟲/殺蟎性質之活性化合物組合（一）
CN111246741B (zh) 2017-10-18 2022-08-02 拜耳公司 具有杀虫/杀螨特性的活性化合物结合物
KR102625757B1 (ko) 2017-10-18 2024-01-17 바이엘 악티엔게젤샤프트 살곤충/살진드기 특성을 갖는 활성 화합물 조합물
TW201930279A (zh) 2017-10-18 2019-08-01 德商拜耳廠股份有限公司 具有殺昆蟲／殺蟎性質之活性化合物組合（三）
US11213031B2 (en) 2017-11-13 2022-01-04 Bayer Aktiengesellschaft Tetrazolylpropyl derivatives and their use as fungicides
WO2019105875A1 (en) 2017-11-28 2019-06-06 Bayer Aktiengesellschaft Heterocyclic compounds as pesticides
AU2018376146A1 (en) 2017-11-29 2020-05-28 Bayer Aktiengesellschaft Nitrogenous heterocycles as a pesticide
AU2018389186A1 (en) 2017-12-20 2020-07-02 Pi Industries Ltd. Fluoralkenyl compounds, process for preparation and use thereof
TW201927768A (zh) 2017-12-21 2019-07-16 德商拜耳廠股份有限公司 三取代矽基甲基雜芳氧基喹啉及類似物
EP3305786A3 (de) 2018-01-22 2018-07-25 Bayer CropScience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
WO2019150311A1 (en) 2018-02-02 2019-08-08 Pi Industries Ltd. 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms
BR112020016234A2 (pt) 2018-02-12 2020-12-15 Bayer Aktiengesellschaft Oxadiazóis fungicidas
WO2019162228A1 (en) 2018-02-21 2019-08-29 Bayer Aktiengesellschaft 1-(5-substituted imidazol-1-yl)but-3-en derivatives and their use as fungicides
US11019821B2 (en) 2018-02-21 2021-06-01 Bayer Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
KR20200129128A (ko) 2018-03-08 2020-11-17 바이엘 악티엔게젤샤프트 식물 보호에서 살충제로서의 헤테로아릴-트리아졸 및 헤테로아릴-테트라졸 화합물의 용도
KR20200131268A (ko) 2018-03-12 2020-11-23 바이엘 악티엔게젤샤프트 해충 방제제로서의 융합된 비시클릭 헤테로시클릭 유도체
AU2019252328A1 (en) 2018-04-10 2020-10-22 Bayer Aktiengesellschaft Oxadiazoline derivatives
US20210147387A1 (en) 2018-04-12 2021-05-20 Bayer Aktiengesellschaft Novel heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides
WO2019197615A1 (de) 2018-04-13 2019-10-17 Bayer Aktiengesellschaft Wirkstoffkombinationen mit fungiziden, insektiziden und akariziden eigenschaften
EP3772960A1 (de) 2018-04-13 2021-02-17 Bayer Aktiengesellschaft Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften
UY38184A (es) 2018-04-17 2019-10-31 Bayer Ag Compuestos heteroarilo-triazol y heteroarilo-tetrazol novedosos como plaguicidas
CN111989328B (zh) 2018-04-20 2023-04-18 拜耳公司 作为害虫防治剂的杂环衍生物
CN112135819A (zh) 2018-04-20 2020-12-25 拜耳公司 作为杀虫剂的杂芳基-三唑与杂芳基-四唑化合物
IL310857A (en) 2018-04-25 2024-04-01 Bayer Ag Heteroaryl-triazole and heteroaryl-tetrazole compounds as pesticides
MX2020011873A (es) 2018-05-09 2021-01-20 Bayer Animal Health Gmbh Nuevos derivados de quinolina.
WO2019224143A1 (de) 2018-05-24 2019-11-28 Bayer Aktiengesellschaft Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften
WO2020005678A1 (en) 2018-06-25 2020-01-02 Bayer Cropscience Lp Seed treatment method
WO2020002189A1 (de) 2018-06-27 2020-01-02 Bayer Aktiengesellschaft Wirkstoffkombinationen
EP3586630A1 (en) 2018-06-28 2020-01-01 Bayer AG Active compound combinations having insecticidal/acaricidal properties
US11401254B2 (en) 2018-07-05 2022-08-02 Bayer Aktiengesellschaft Substituted thiophenecarboxamides and analogues as antibacterials agents
WO2020020813A1 (en) 2018-07-25 2020-01-30 Bayer Aktiengesellschaft Fungicidal active compound combinations
WO2020020816A1 (en) 2018-07-26 2020-01-30 Bayer Aktiengesellschaft Novel triazole derivatives
KR20210038617A (ko) 2018-07-27 2021-04-07 바이엘 악티엔게젤샤프트 농약용 제어 방출 제제
AU2019313545A1 (en) 2018-07-31 2021-02-25 Bayer Aktiengesellschaft Controlled release formulations with lignin for agrochemicals
AR115984A1 (es) 2018-08-17 2021-03-17 Pi Industries Ltd Compuestos de 1,2-ditiolona y sus usos
WO2020043650A1 (en) 2018-08-29 2020-03-05 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
WO2020053282A1 (de) 2018-09-13 2020-03-19 Bayer Aktiengesellschaft Heterocyclen-derivate als schädlingsbekämpfungsmittel
CN112714614A (zh) 2018-09-17 2021-04-27 拜耳公司 杀真菌剂异氟普仑用于在谷物中防治麦角菌和减少菌核的用途
WO2020070050A1 (en) 2018-10-01 2020-04-09 Bayer Aktiengesellschaft Fungicidal 5-substituted imidazol-1-yl carbinol derivatives
EP3636644A1 (de) 2018-10-11 2020-04-15 Bayer Aktiengesellschaft Mesoionische imidazopyridine als insektizide
WO2020078839A1 (de) 2018-10-16 2020-04-23 Bayer Aktiengesellschaft Wirkstoffkombinationen
EP3867241A1 (en) 2018-10-18 2021-08-25 Bayer Aktiengesellschaft Pyridylphenylaminoquinolines and analogues
BR112021007333A2 (pt) 2018-10-18 2021-07-20 Bayer Aktiengesellschaft heteroarilaminoquinolinas e análogos
TW202028193A (zh) 2018-10-20 2020-08-01 德商拜耳廠股份有限公司 氧雜環丁基苯氧基喹啉及類似物
EP3643711A1 (en) 2018-10-24 2020-04-29 Bayer Animal Health GmbH New anthelmintic compounds
AR117169A1 (es) 2018-11-28 2021-07-14 Bayer Ag (tio)amidas de piridazina como compuestos fungicidas
CN111269237B (zh) * 2018-12-04 2022-05-24 南开大学 偕二氟化螺-γ-内酰胺吲哚啉化合物及其制备方法和在防治植物病虫害中的应用
PL3890488T3 (pl) 2018-12-07 2023-05-02 Bayer Aktiengesellschaft Kompozycje herbicydowe
EP3890489B1 (de) 2018-12-07 2023-01-04 Bayer Aktiengesellschaft Herbizide zusammensetzungen
EP3620052A1 (en) 2018-12-12 2020-03-11 Bayer Aktiengesellschaft Use of phenoxypyridinyl-substituted (1h-1,2,4-triazol-1-yl)alcohols for controlling fungicidal diseases in maize
US20220061323A1 (en) 2018-12-18 2022-03-03 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
EP3898620A1 (en) 2018-12-20 2021-10-27 Bayer Aktiengesellschaft Heterocyclyl pyridazine as fungicidal compounds
EP3669652A1 (en) 2018-12-21 2020-06-24 Bayer AG Active compound combination
BR112021009908A2 (pt) 2018-12-21 2021-08-17 Bayer Aktiengesellschaft 1,3,4-oxadiazóis e derivados dos mesmos como novos agentes antifúngicos
EP3679793A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679792A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679791A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679790A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3679789A1 (en) 2019-01-08 2020-07-15 Bayer AG Active compound combinations
EP3545764A1 (en) 2019-02-12 2019-10-02 Bayer AG Crystal form of 2-({2-fluoro-4-methyl-5-[(r)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2- trifluoroethyl)-1,3-thiazolidin-4-one
WO2020173860A1 (en) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
WO2020173861A1 (de) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
BR112021009703A2 (pt) 2019-03-01 2021-11-23 Bayer Ag Combinações de compostos ativos tendo propriedades inseticidas/acaricidas
WO2020178307A1 (en) 2019-03-05 2020-09-10 Bayer Aktiengesellschaft Active compound combination
WO2020182929A1 (en) 2019-03-13 2020-09-17 Bayer Aktiengesellschaft Substituted ureas and derivatives as new antifungal agents
US20220183293A1 (en) 2019-03-15 2022-06-16 Bayer Aktiengesellschaft Active compound combinations having insecticidal/acaricidal properties
EP3564225A1 (en) 2019-03-21 2019-11-06 Bayer Aktiengesellschaft Crystalline form of spiromesifen
EP3725788A1 (en) 2019-04-15 2020-10-21 Bayer AG Novel heteroaryl-substituted aminoalkyl azole compounds as pesticides
WO2020225242A1 (en) 2019-05-08 2020-11-12 Bayer Aktiengesellschaft Active compound combination
BR112021022428A2 (pt) 2019-05-08 2021-12-28 Bayer Ag Formulações de ulv de alto espalhamento para compostos agroquímicos ii
US20220240508A1 (en) 2019-05-10 2022-08-04 Bayer Cropscience Lp Active compound combinations
WO2020229398A1 (de) 2019-05-14 2020-11-19 Bayer Aktiengesellschaft (1-alkenyl)-substituierte pyrazole und triazole als schädlingsbekämpfungsmittel
EP3750888A1 (en) 2019-06-12 2020-12-16 Bayer Aktiengesellschaft Crystalline form a of 1,4-dimethyl-2-[2-(pyridin-3-yl)-2h-indazol-5-yl]-1,2,4-triazolidine-3,5-dione
WO2020254489A1 (en) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Benzylphenyl hydroxyisoxazolines and analogues as new antifungal agents
BR112021025300A2 (pt) 2019-06-21 2022-02-01 Bayer Ag Oxadiazóis fungicidas
WO2020254493A1 (en) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Thienylhydroxyisoxazolines and derivatives thereof
EP3986876A1 (en) 2019-06-21 2022-04-27 Bayer Aktiengesellschaft Hydroxyisoxazolines and derivatives thereof
EP3986891A1 (en) 2019-06-21 2022-04-27 Bayer Aktiengesellschaft Hydroxyisoxazolines and derivatives thereof
WO2020254490A1 (en) 2019-06-21 2020-12-24 Bayer Aktiengesellschaft Phenoxyphenyl hydroxyisoxazolines and analogues as new antifungal agents
BR112021025305A2 (pt) 2019-06-21 2022-02-01 Bayer Ag Hidroxi-isoxazolinas e uso das mesmas como fungicidas
BR112021025700A2 (pt) 2019-06-21 2022-02-08 Bayer Ag Hidróxi-isoxazolinas e derivados das mesmas
WO2020263812A1 (en) 2019-06-24 2020-12-30 Auburn University A bacillus strain and methods of its use for plant growth promotion
EP3608311A1 (en) 2019-06-28 2020-02-12 Bayer AG Crystalline form a of n-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide
JP2022538262A (ja) 2019-07-03 2022-09-01 バイエル・アクチエンゲゼルシヤフト 殺菌薬としての置換されたチオフェンカルボキサミド類及びそれの誘導体
WO2021001273A1 (de) 2019-07-04 2021-01-07 Bayer Aktiengesellschaft Herbizide zusammensetzungen
EP3771714A1 (de) 2019-07-30 2021-02-03 Bayer AG Stickstoffhaltige heterocyclen als schädlingsbekämpfungsmittel
TW202120490A (zh) 2019-07-30 2021-06-01 德商拜耳動物保健有限公司 新穎異喹啉衍生物
EP3701796A1 (en) 2019-08-08 2020-09-02 Bayer AG Active compound combinations
RU2713902C1 (ru) * 2019-08-27 2020-02-10 Владимир Георгиевич Григулецкий Органическое ростовое вещество
BR112022004347A8 (pt) 2019-09-11 2022-10-18 Bayer Ag Formulações altamente eficazes à base de 2-[(2,4-diclorofenil)-metil]-4,4'-dimetil-3-isoxazolidinona e herbicidas de pré-emergência
US20220403410A1 (en) 2019-09-26 2022-12-22 Bayer Aktiengesellschaft Rnai-mediated pest control
TW202128650A (zh) 2019-10-11 2021-08-01 德商拜耳動物保健有限公司 作為殺蟲劑之新穎的雜芳基取代之吡𠯤衍生物
EP4055010A1 (de) 2019-11-07 2022-09-14 Bayer Aktiengesellschaft Substituierte sulfonylamide zur bekämpfung tierischer schädlinge
WO2021097162A1 (en) 2019-11-13 2021-05-20 Bayer Cropscience Lp Beneficial combinations with paenibacillus
CR20220293A (es) 2019-12-20 2022-08-03 Bayer Ag Tieniloxazolonas y análogos
EP4285723A3 (en) 2019-12-20 2024-03-27 Bayer Aktiengesellschaft Substituted thiophene carboxamides, thiophene carboxylic acids and derivatives thereof
EP3845304A1 (en) 2019-12-30 2021-07-07 Bayer AG Capsule suspension concentrates based on polyisocyanates and biodegradable amine based cross-linker
BR112022016400A2 (pt) 2020-02-18 2022-10-25 Bayer Ag Compostos inovadores de heteroaril-triazol como pesticidas
EP3868207A1 (de) 2020-02-24 2021-08-25 Bayer Aktiengesellschaft Verkapselte pyrethroide mit verbesserter wirksamkeit bei boden- und blattanwendungen
EP3708565A1 (en) 2020-03-04 2020-09-16 Bayer AG Pyrimidinyloxyphenylamidines and the use thereof as fungicides
CA3179528A1 (en) 2020-04-09 2021-10-14 Bayer Animal Health Gmbh Substituted condensed azines as anthelmintic compounds
WO2021209368A1 (en) 2020-04-16 2021-10-21 Bayer Aktiengesellschaft Active compound combinations and fungicide compositions comprising those
BR112022020704A2 (pt) 2020-04-16 2022-11-29 Bayer Ag Combinações de compostos ativos e composições fungicidas compreendendo os mesmos
CN115515426A (zh) 2020-04-16 2022-12-23 拜耳公司 活性化合物组合以及包含它们的杀真菌剂组合物
AR122415A1 (es) 2020-04-16 2022-09-07 Bayer Ag Combinaciones de compuestos activos y composiciones fungicidas que los comprenden
WO2021209490A1 (en) 2020-04-16 2021-10-21 Bayer Aktiengesellschaft Cyclaminephenylaminoquinolines as fungicides
EP4135523A1 (en) 2020-04-16 2023-02-22 Bayer Aktiengesellschaft Active compound combinations and fungicide compositions comprising those
US20230348392A1 (en) 2020-05-06 2023-11-02 Bayer Aktiengesellschaft Pyridine (thio)amides as fungicidal compounds
US20230180756A1 (en) 2020-05-12 2023-06-15 Bayer Aktiengesellschaft Triazine and pyrimidine (thio)amides as fungicidal compounds
EP4153566A1 (en) 2020-05-19 2023-03-29 Bayer CropScience Aktiengesellschaft Azabicyclic(thio)amides as fungicidal compounds
BR112022024394A2 (pt) 2020-06-04 2023-01-31 Bayer Ag Heterociclil pirimidinas e triazinas como novos fungicidas
CN116057056A (zh) 2020-06-10 2023-05-02 拜耳公司 作为杀真菌剂的氮杂双环取代的杂环化合物
WO2021255071A1 (en) 2020-06-18 2021-12-23 Bayer Aktiengesellschaft 3-(pyridazin-4-yl)-5,6-dihydro-4h-1,2,4-oxadiazine derivatives as fungicides for crop protection
UY39276A (es) 2020-06-19 2022-01-31 Bayer Ag Uso de compuestos de 1,3,4–oxadiazol–2–ilpirimidina para controlar microorganismos fitopatógenos, métodos de uso y composiciones.
WO2021255089A1 (en) 2020-06-19 2021-12-23 Bayer Aktiengesellschaft 1,3,4-oxadiazole pyrimidines and 1,3,4-oxadiazole pyridines as fungicides
UY39275A (es) 2020-06-19 2022-01-31 Bayer Ag 1,3,4-oxadiazol pirimidinas como fungicidas, procesos e intermediarios para su preparación, métodos de uso y usos de los mismos
WO2021255091A1 (en) 2020-06-19 2021-12-23 Bayer Aktiengesellschaft 1,3,4-oxadiazoles and their derivatives as fungicides
US20230247986A1 (en) 2020-06-26 2023-08-10 Bayer Aktiengesellschaft Aqueous capsule suspension concentrates comprising biodegradable ester groups
WO2022058327A1 (en) 2020-09-15 2022-03-24 Bayer Aktiengesellschaft Substituted ureas and derivatives as new antifungal agents
EP3915371A1 (en) 2020-11-04 2021-12-01 Bayer AG Active compound combinations and fungicide compositions comprising those
EP3994992A1 (en) 2020-11-08 2022-05-11 Bayer AG Low drift, rainfastness, high uptake and ulv tank mix adjuvant formulation
EP3994995A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Low drift, rainfastness, high spreading, high uptake and ulv tank mix adjuvant formulation
EP3994986A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Agrochemical composition with improved drift and spreading properties
EP3994990A1 (en) 2020-11-08 2022-05-11 Bayer AG Agrochemical composition with improved drift, spreading and uptake properties
EP3994989A1 (en) 2020-11-08 2022-05-11 Bayer AG Agrochemical composition with improved drift, rainfastness and uptake properties
EP3994985A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Agrochemical composition with improved drift properties
EP3994993A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Low drift, rainfastness, high spreading and ulv tank mix adjuvant formulation
EP3994987A1 (en) 2020-11-08 2022-05-11 Bayer AG Agrochemical composition with improved drift and uptake properties
EP3994988A1 (en) 2020-11-08 2022-05-11 Bayer AG Agrochemical composition with improved drift, spreading and rainfastness properties
EP3994991A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Agrochemical composition with improved drift, spreading, uptake and rainfastness properties
EP3994994A1 (en) 2020-11-08 2022-05-11 Bayer Aktiengesellschaft Low drift, rainfastness, high spreading, high uptake and ulv tank mix adjuvant formulation
EP3915971A1 (en) 2020-12-16 2021-12-01 Bayer Aktiengesellschaft Phenyl-s(o)n-phenylamidines and the use thereof as fungicides
WO2022129190A1 (en) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft (hetero)aryl substituted 1,2,4-oxadiazoles as fungicides
WO2022129196A1 (en) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft Heterobicycle substituted 1,2,4-oxadiazoles as fungicides
WO2022129188A1 (en) 2020-12-18 2022-06-23 Bayer Aktiengesellschaft 1,2,4-oxadiazol-3-yl pyrimidines as fungicides
WO2022152728A1 (de) 2021-01-15 2022-07-21 Bayer Aktiengesellschaft Herbizide zusammensetzungen
WO2022162129A1 (en) 2021-01-28 2022-08-04 Rhodia Operations Method for treating rice seed with improved retention of agrochemical, micronutrient and colorant
BR112023022046A2 (pt) 2021-05-10 2023-12-26 Bayer Ag Combinação de herbicida/protetor baseada em protetores da classe dos ácidos [(1,5-difenil-1h-1,2,4-triazol-3-il)óxi]acéticos substituídos e seus sais
EP4148052A1 (en) 2021-09-09 2023-03-15 Bayer Animal Health GmbH New quinoline derivatives
WO2023078915A1 (en) 2021-11-03 2023-05-11 Bayer Aktiengesellschaft Bis(hetero)aryl thioether (thio)amides as fungicidal compounds
WO2023092050A1 (en) 2021-11-20 2023-05-25 Bayer Cropscience Lp Beneficial combinations with recombinant bacillus cells expressing a serine protease
WO2023099445A1 (en) 2021-11-30 2023-06-08 Bayer Aktiengesellschaft Bis(hetero)aryl thioether oxadiazines as fungicidal compounds
WO2023110656A1 (en) 2021-12-15 2023-06-22 Bayer Aktiengesellschaft Spectroscopic solution for non-destructive quantification of one or more chemical substances in a matrix comprising coating and bulk material in a sample, such as coated seeds, using multivariate data analysis
WO2023205602A1 (en) 2022-04-18 2023-10-26 Basf Corporation High-load agricultural formulations and methods of making same
EP4265110A1 (en) 2022-04-20 2023-10-25 Bayer AG Water dispersible granules with low melting active ingredients prepared by extrusion
WO2023217619A1 (en) 2022-05-07 2023-11-16 Bayer Aktiengesellschaft Low drift aqueous liquid formulations for low, medium, and high spray volume application
WO2024013016A1 (en) 2022-07-11 2024-01-18 Bayer Aktiengesellschaft Herbicidal compositions
WO2024013015A1 (en) 2022-07-11 2024-01-18 Bayer Aktiengesellschaft Herbicidal compositions
WO2024068473A1 (de) 2022-09-27 2024-04-04 Bayer Aktiengesellschaft Herbizid/safener-kombinationen basierend auf safenern aus der klasse der substituierten [(1,5-diphenyl1h-1,2,4-triazol-3-yl)oxy]essigsäuren sowie deren salze
EP4353082A1 (en) 2022-10-14 2024-04-17 Bayer Aktiengesellschaft Herbicidal compositions

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3959475A (en) * 1973-12-12 1976-05-25 American Hoechst Corporation Substituted 1,3-dihydrospiro(isobenzofuran)s
US4233307A (en) * 1978-02-13 1980-11-11 Sumitomo Chemical Company, Limited Spiro-4'-piperidine compounds and their pharmaceutical compositions
US4307235A (en) * 1978-08-23 1981-12-22 American Hoechst Corporation Spiro[indoline-3,4'-piperidine]s

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES468860A1 (es) 1977-04-21 1979-09-16 Hoechst Ag Un procedimiento para preparar espiro (indolin-3,4'-piperi- dina)s.
US4209625A (en) 1977-04-21 1980-06-24 American Hoechst Corporation Spiro[indoline-3,4'-piperidine]s
GB1575800A (en) 1978-05-16 1980-10-01 Sumitomo Chemical Co Spiro amines their production and compositions containing them
JPH0720647B2 (ja) 1987-11-24 1995-03-08 松下電工株式会社 成形金型のスプルーブッシュ
US5578593A (en) * 1992-12-11 1996-11-26 Merck & Co., Inc. Spiro piperidines and homologs promote release of growth hormone
EP0702681A1 (en) 1993-06-07 1996-03-27 Merck & Co. Inc. Spiro-substituted azacycles as neurokinin antagonists
JP3542805B2 (ja) * 1993-07-02 2004-07-14 バイエル・アクチエンゲゼルシヤフト 置換スピロ複素環式１ｈ−３−アリールピロリジン−２、４−ジオン誘導体、それらの製造方法および有害生物防除剤としてのそれらの使用
JPH0720647A (ja) 1993-07-02 1995-01-24 Mitsubishi Paper Mills Ltd 電子写真感光体
KR960705575A (ko) 1993-10-19 1996-11-08 도나 엘. 폴락 비스포스포네이트와 성장 호르몬 분비촉진제와의 배합물(Combination of bishosphonates and growth hormone secretagogues)
GB9417956D0 (en) 1994-09-02 1994-10-26 Merck Sharp & Dohme Therapeutic agents
WO1998025605A1 (en) 1996-12-13 1998-06-18 Merck & Co., Inc. Spiro-substituted azacycles as modulators of chemokine receptor activity
US5962462A (en) * 1996-12-13 1999-10-05 Merck & Co., Inc. Spiro-substituted azacycles as modulators of chemokine receptor activity
US5783579A (en) 1996-12-20 1998-07-21 Schering Corporation Spiro-substituted azacyclic-substituted piperazino derivatives as neurokinin antagonists
WO1999064002A1 (en) 1998-06-11 1999-12-16 Merck & Co., Inc. Spiropiperidine derivatives as melanocortin receptor agonists
US20020128208A1 (en) 2000-12-15 2002-09-12 Snyder James P. Nonpeptide agonists and antagonists of vasopressin receptors
ATE460163T1 (de) 2001-04-12 2010-03-15 Pharmacopeia Llc Arly und diaryl piperidinderivate verwendbar als mch-hemmer
GB0213715D0 (en) * 2002-06-14 2002-07-24 Syngenta Ltd Chemical compounds
GB0328908D0 (en) * 2003-12-12 2004-01-14 Syngenta Participations Ag Chemical compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3959475A (en) * 1973-12-12 1976-05-25 American Hoechst Corporation Substituted 1,3-dihydrospiro(isobenzofuran)s
US4233307A (en) * 1978-02-13 1980-11-11 Sumitomo Chemical Company, Limited Spiro-4'-piperidine compounds and their pharmaceutical compositions
US4307235A (en) * 1978-08-23 1981-12-22 American Hoechst Corporation Spiro[indoline-3,4'-piperidine]s

Cited By (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080047479A1 (en) * 1997-10-27 2008-02-28 Correct Craft, Inc. Water Sport Towing Apparatus and Method
US8071624B2 (en) 2004-06-24 2011-12-06 Incyte Corporation N-substituted piperidines and their use as pharmaceuticals
US20050288329A1 (en) * 2004-06-24 2005-12-29 Wenqing Yao 2-Methylprop anamides and their use as pharmaceuticals
US20060004049A1 (en) * 2004-06-24 2006-01-05 Wenqing Yao N-substituted piperidines and their use as pharrmaceuticals
US20060009471A1 (en) * 2004-06-24 2006-01-12 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20060009491A1 (en) * 2004-06-24 2006-01-12 Incyte Corporation Amido compounds and their use as pharmaceuticals
US8288417B2 (en) 2004-06-24 2012-10-16 Incyte Corporation N-substituted piperidines and their use as pharmaceuticals
US7687665B2 (en) 2004-06-24 2010-03-30 Incyte Corporation 2-methylprop anamides and their use as pharmaceuticals
US20050288338A1 (en) * 2004-06-24 2005-12-29 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20050288317A1 (en) * 2004-06-24 2005-12-29 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20060122197A1 (en) * 2004-08-10 2006-06-08 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20100311720A1 (en) * 2004-08-19 2010-12-09 Vertex Pharmaceuticals Incorporated Spiroindoline Modulators of Muscarinic Receptors
US7879834B2 (en) 2004-08-19 2011-02-01 Vertex Pharmaceuticals Incorporated Spiroindoline modulators of muscarinic receptors
US8367691B2 (en) 2004-08-19 2013-02-05 Vertex Pharmaceutical Incorporated Modulators of muscarinic receptors
US8258148B2 (en) 2004-08-19 2012-09-04 Vertex Pharmaceutical Incorporated Spiroindoline modulators of muscarinic receptors
US7786141B2 (en) 2004-08-19 2010-08-31 Vertex Pharmaceuticals Incorporated Dihydrospiroindene modulators of muscarinic receptors
US8497295B2 (en) 2004-08-19 2013-07-30 Vertex Pharmaceuticals Incorporated Spiroindoline modulators of muscarinic receptors
US20100311746A1 (en) * 2004-08-19 2010-12-09 Vertex Pharmaceuticals Incorporated Modulators of muscarinic receptors
US8110581B2 (en) 2004-11-10 2012-02-07 Incyte Corporation Lactam compounds and their use as pharmaceuticals
US20090291946A1 (en) * 2004-11-10 2009-11-26 Incyte Corporation Lactam compounds and their use as pharmaceuticals
US8563570B2 (en) 2004-11-10 2013-10-22 Incyte Corporation Lactam compounds and their use as pharmaceuticals
US20060116382A1 (en) * 2004-11-10 2006-06-01 Wenqing Yao Lactam compounds and their use as pharmaceuticals
US20060122210A1 (en) * 2004-11-18 2006-06-08 Wenqing Yao Inhibitors of 11-beta hydroxyl steroid dehydrogenase type I and methods of using the same
US20060270653A1 (en) * 2004-11-29 2006-11-30 Ioana Drutu Modulators of muscarinic receptors
US7863449B2 (en) 2004-11-29 2011-01-04 Vertex Pharmaceuticals Incorporated Modulators of muscarinic receptors
US20070066584A1 (en) * 2005-09-21 2007-03-22 Wenqing Yao Amido compounds and their use as pharmaceuticals
US20070129345A1 (en) * 2005-12-05 2007-06-07 Jincong Zhuo Lactam compounds and methods of using the same
US8193207B2 (en) 2005-12-05 2012-06-05 Incyte Corporation Lactam compounds and methods of using the same
US20080015179A1 (en) * 2005-12-22 2008-01-17 Makings Lewis R Modulators of muscarinic receptors
US7858635B2 (en) 2005-12-22 2010-12-28 Vertex Pharmaceuticals Incorporated Spiro compounds as modulators of muscarinic receptors
US7998959B2 (en) 2006-01-12 2011-08-16 Incyte Corporation Modulators of 11-β hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same
US20070197506A1 (en) * 2006-01-12 2007-08-23 Wenqing Yao Modulators of 11-beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same
US20070197530A1 (en) * 2006-01-31 2007-08-23 Yun-Long Li Amido compounds and their use as pharmaceuticals
US20070213315A1 (en) * 2006-02-22 2007-09-13 Robert Davies Modulators of muscarinic receptors
US8003660B2 (en) 2006-02-22 2011-08-23 Vertex Pharmaceuticals Incorporated Modulators of muscarinic receptors
US8304423B2 (en) 2006-02-22 2012-11-06 Vertex Pharmaceutical Incorporated Modulators of muscarinic receptors
US20070213311A1 (en) * 2006-03-02 2007-09-13 Yun-Long Li Modulators of 11-beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same
US20070208001A1 (en) * 2006-03-03 2007-09-06 Jincong Zhuo Modulators of 11- beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same
US20070293529A1 (en) * 2006-05-01 2007-12-20 Yun-Long Li Tetrasubstituted ureas as modulators of 11-beta hydroxyl steroid dehydrogenase type 1
US20070270424A1 (en) * 2006-05-17 2007-11-22 Yun-Long Li Heterocyclic inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1 and methods of using the same
US7838544B2 (en) 2006-05-17 2010-11-23 Incyte Corporation Heterocyclic inhibitors of 11-β hydroxyl steroid dehydrogenase type 1 and methods of using the same
US7786107B2 (en) 2006-08-18 2010-08-31 Vertex Pharmaceuticals Incorporated Modulators of muscarinic receptors
US20080318991A1 (en) * 2007-06-21 2008-12-25 Incyte Corporation Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1
US8278318B2 (en) 2007-06-21 2012-10-02 Incyte Corporation Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1
US9006260B2 (en) 2007-06-21 2015-04-14 Incyte Corporation Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1
US9371323B2 (en) 2007-06-21 2016-06-21 Incyte Holdings Corporation Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1
US9873698B2 (en) 2007-06-21 2018-01-23 Incyte Holdings Corporation Spirocycles as inhibitors of 11-beta hydroxyl steroid dehydrogenase type 1
US20090099222A1 (en) * 2007-10-03 2009-04-16 Davies Robert J Modulators of muscarinic receptors
US7973162B2 (en) 2007-10-03 2011-07-05 Vertex Pharmaceuticals Incorporated Modulators of muscarinic receptors

Also Published As

Publication number Publication date
CN101574084A (zh) 2009-11-11
EA200401540A1 (ru) 2005-06-30
EP1515969B2 (en) 2017-10-11
AP1850A (en) 2008-05-26
CO5621237A2 (es) 2006-03-31
AR040208A1 (es) 2005-03-16
GB0213715D0 (en) 2002-07-24
ATE478870T1 (de) 2010-09-15
IL165226A0 (en) 2005-12-18
CN101318958A (zh) 2008-12-10
CN1662535A (zh) 2005-08-31
IL213984A0 (en) 2011-08-31
NZ536734A (en) 2006-03-31
CN101318958B (zh) 2011-06-15
AU2003240071B2 (en) 2009-09-10
AP2005003198A0 (en) 2005-03-31
JP4837913B2 (ja) 2011-12-14
PT1515969E (pt) 2010-11-29
KR101013428B1 (ko) 2011-02-14
US9686990B2 (en) 2017-06-27
UA81767C2 (uk) 2008-02-11
CN101574084B (zh) 2013-05-08
EP1515969B1 (en) 2010-08-25
KR20050019135A (ko) 2005-02-28
CN1944431A (zh) 2007-04-11
CA2487494A1 (en) 2003-12-24
ES2351188T3 (es) 2011-02-01
CN1662535B (zh) 2011-09-07
JP2006501170A (ja) 2006-01-12
US20120010220A1 (en) 2012-01-12
EP1880996A1 (en) 2008-01-23
DK1515969T3 (da) 2010-12-13
CA2487494C (en) 2011-07-19
US20160007608A1 (en) 2016-01-14
US9174987B2 (en) 2015-11-03
ZA200410058B (en) 2005-11-30
DE60333919D1 (de) 2010-10-07
EA014223B1 (ru) 2010-10-29
SI1515969T1 (sl) 2011-01-31
MA27365A1 (fr) 2005-06-01
AU2003240071A1 (en) 2003-12-31
TW200402265A (en) 2004-02-16
MXPA04012349A (es) 2005-02-25
IL165226A (en) 2011-08-31
CY1111822T1 (el) 2015-10-07
EP1515969A1 (en) 2005-03-23
WO2003106457A1 (en) 2003-12-24
EP1880996B1 (en) 2014-12-24
TWI343784B (en) 2011-06-21
BR0312129A (pt) 2005-03-29
BR0312129B1 (pt) 2014-09-02

Similar Documents

Publication Publication Date Title
US9686990B2 (en) Spiroindolinepiperidine derivatives
US8110593B2 (en) Phenoxymethyl imidazoline derivatives and their use as pesticides
US7960401B2 (en) Spiropiperidine derivatives for controlling pests
US8110684B2 (en) Diaza-spiro [4.5] decanes useful as pesticides
EP1694676A1 (en) Spiroindoline derivatives having insecticidal properties
EP1732385A1 (en) Use of (3-(1-(3-phenyl-propenyl)-piperidin-4-yl)-2,3-dihydro-indol-1-yl)-(pyridin-4-yl)-methanone derivatives and related compounds as insecticides
US8586593B2 (en) Insecticidal compounds
US20140031378A1 (en) Insecticidal spironindane derivatives
WO2005061512A1 (en) Spiro-condensed indoline derivates as pesticides
EP2207421B1 (en) Haloalkylsubstituted aryloxyalkylimidazolines for use as pesticides
US8338443B2 (en) Chemical compounds
WO2007060541A2 (en) Piperazine derivatives and their use as insecticides, acaricides, molluscicides, and nematicides

Legal Events

Date Code Title Description
AS Assignment

Owner name: SYNGENTA PARTICIPATIONS AG, SWITZERLAND

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ROBERTS, RICHARD SPURRING;MOLLEYRES, LOUIS-PIERRE;CEDERBAUM, FREDRIK;AND OTHERS;REEL/FRAME:022546/0963;SIGNING DATES FROM 20061213 TO 20070123

Owner name: SYNGENTA LIMITED, UNITED KINGDOM

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ASHTON, MARK RICHARD;HUGHES, DAVID JOHN;WORTHINGTON, PAUL ANTHONY;AND OTHERS;REEL/FRAME:022547/0051;SIGNING DATES FROM 20061208 TO 20081215

STCB Information on status: application discontinuation

Free format text: ABANDONED -- AFTER EXAMINER'S ANSWER OR BOARD OF APPEALS DECISION