EP0944314A1 - Methyl substituierte fungizide und arthropodizide - Google Patents

Methyl substituierte fungizide und arthropodizide

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Publication number
EP0944314A1
EP0944314A1 EP97948597A EP97948597A EP0944314A1 EP 0944314 A1 EP0944314 A1 EP 0944314A1 EP 97948597 A EP97948597 A EP 97948597A EP 97948597 A EP97948597 A EP 97948597A EP 0944314 A1 EP0944314 A1 EP 0944314A1
Authority
EP
European Patent Office
Prior art keywords
phenyl
pyridinyl
ocf
dime
naphthalenyl
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.)
Withdrawn
Application number
EP97948597A
Other languages
English (en)
French (fr)
Inventor
Richard James Brown
Peter Paul Castro
Dominic Ming-Tak Chan
John Powell Daub
Gerard Michael Koether
Thomas Paul Selby
Paula Louise Sharpe
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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
Priority claimed from PCT/US1996/018916 external-priority patent/WO1998023155A1/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0944314A1 publication Critical patent/EP0944314A1/de
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/12—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si

Definitions

  • This invention relates to certain methyl substituted fungicides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides and arthropodicides.
  • the control of plant diseases caused by fungal plant pathogens is extremely important in achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal, and fruit crops can cause significant reduction in productivity and thereby result in increased costs to the consumers.
  • the control of arthropod pests is also extremely important in achieving high crop efficiency. Arthropod damage to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer.
  • the control of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
  • X is OR 1 , SCOJ ⁇ J R 1 or halogen;
  • A is O, S, N, NR 5 or CR 7 ;
  • G is C or N; provided that when G is C, A is O, S or NR 5 and the floating double bond is attached to G; and when G is N, A is N or CR 7 and the floating double bond is attached to A;
  • W is O; S; NH; N(C r C 6 alkyl); or NO(C r C 6 alkyl);
  • Y linkage is defined such that the moiety depicted on the left side of the linkage is bonded to the phenyl ring having the R 3 and R 4 substituents and the moiety on the right side of the linkage is bonded to Z;
  • Z is independently selected from: i) C]-C JO alkyl, CI -CJ Q haloalkyl or phenyl each optionally substituted with R 9 and optionally substituted with one or more R 10 ; ii) a ring selected from 5 or 6-membered aromatic heterocyclic ring, each heterocyclic ring containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring contains no more than 3 nitrogens, no more than 1 oxygen, and
  • R 7 is H, halogen or methyl
  • R 8 is H, C r C 3 alkyl, C r C 3 alkoxy, C r C 3 alkylthio, C r C 3 haloalkyl, C 2 -C 3 alkenyl,
  • R 9 is halogen; Ci-C alkyl; C j -Cg haloalkyl; C j -Cg alkoxy; C Cg haloalkoxy; C 2 -Cg alkenyl; C 2 -C 6 haloalkenyl; C 2 -Cg alkynyl; C j -Cg alkylthio;
  • R 12 is halogen, Cj-Cg alkyl, Cj-Cg haloalkyl, C j -C 6 alkoxy, C j -Cg haloalkoxy, C 2 -Cg alkenyl, C 2 -Cg haloalkenyl, C 2 -Cg alkynyl, C j -Cg alkylthio, C r C 6 haloalkylthio, C r C 6 alkylsulfinyl, C r C 6 alkylsulfonyl or C 3 -C 6 cycloalkyl;
  • R 13 is halogen, Cj-Cg alkyl, Cj-Cg haloalkyl, C j -Cg alkoxy, C j -Cg haloalkoxy or cyano; m is 0, 1 or 2; n is 0, 1 or 2; r is 1, 2, 3 or 4; and s is 0 or 1.
  • This invention provides a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula I including all geometric and stereoisomers, N-oxide, and agriculturally suitable salts thereof, provided that when T is T 1 , then i) when Y is -O-, X is OMe, R 3 is CH 3 and R 4 is H, then Z is other than 6-chloro-4-pyrimidinyl and 6-chloro-2-pyrazinyl; ii) when Y is a direct bond, X is Cl, R 3 is CH 3 and R 4 is H, then Z is other than
  • This invention also provides selected compounds of Formula I which are considered particularly effective fungicides and arthropodicides. Specifically, this invention provides compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, and agricultural compositions containing them and their use as fungicides and arthropodicides, provided that
  • R 10 other than methyl and halogen; and ix) when Y is -CH 2 O-, R 3 is CH 3 , Z is phenyl substituted with R 10 in the 2-position and R 10 is methyl or halogen, then Z is substituted with at least one
  • R 9 or R 10 other than methyl and halogen
  • haloalkylthio straight-chain or branched alkyl, such as, methyl, ethyl, r ⁇ -propyl, z ' -propyl, or the different butyl, pentyl or hexyl isomers.
  • alkyl used alone or in the compound word “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, «-propyl, z ' -propyl, or the different butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl isomers.
  • Alkenyl includes straight-chain or branched alkenes such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers.
  • Alkenyl also includes polyenes such as 1 ,2-propadienyl and 2,4-hexadienyl.
  • Alkynyl includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • Alkoxy includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group.
  • alkylsulfinyl examples include CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.
  • alkylsulfonyl examples include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • halogen either alone or in compound words such as “haloalkyl” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkenyl “haloalkynyl”, “haloalkoxy”, “haloalkylthio”, and the like, are defined analogously to the term “haloalkyl”.
  • haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CC1 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkylthio examples include CC1 3 S, CF 3 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S.
  • aromatic heterocyclic rings are defined as those rings which satisfy the H ⁇ ckel rule. Examples include: a 5- or 6- membered aromatic heterocyclic ring containing 1 to 4 heteroatoms such as furanyl, furazanyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, oxadiazolyl, imidazolyl, isoxazolyl, thiazolyl, thiadiazolyl isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl and triazinyl with said ring attached through any available carbon or nitrogen.
  • the aromatic heterocyclic ring when the aromatic heterocyclic ring is furanyl, it can be 2-furanyl or 3-furanyl, for pyrrolyl, the aromatic heterocyclic ring is 1 -pyrrolyl, 2-pyrrolyl or 3-pyrrolyl, for pyridyl, the aromatic ring is 2-pyridyl, 3-pyridyl or 4-pyridyl and similarly for other aromatic heterocyclic rings.
  • the Y substituent is preferably attached to the aromatic ring of the tetrahydronaphthalene (i.e., the ring which satisfies the H ⁇ ckel rule).
  • Cj-C The total number of carbon atoms in a substituent group is indicated by the "Cj-C;" prefix where i and j are numbers from 1 to 10.
  • C j -C 3 alkylthio designates methylthio through propylthio.
  • alkylcarbonyl include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
  • a group contains a substituent which can be hydrogen, for example R 2 or R 7 , then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.
  • a group is optionally substituted with a substituent, for example with R 1 , then, when the group is not substituted with that substituent, it is recognized that this is equivalent to said group having a hydrogen substituent.
  • Compounds of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). (See, e.g., U.S. Provisional Patent Application Serial No.
  • the present invention comprises compounds selected from Formula I and agriculturally suitable salts thereof.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
  • the salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • Preferred compounds for reasons of better activity and/or ease of synthesis are: Preferred 1.
  • Z is phenyl, pyridinyl, thiazolyl or thiadiazolyl, each optionally substituted with R 9 and optionally substituted with one or more R 10 ;
  • R 9 is halogen, C j -Cg alkyl, C j -Cg alkoxy, C j -Cg haloalkyl or C Cg haloalkoxy;
  • R 10 is halogen, C r C 6 alkyl, C r C 6 alkoxy, C r C 6 haloalkyl or
  • Z is phenyl, pyridinyl, thiazolyl or thiadiazolyl, each optionally substituted with R 9 and optionally substituted with one or more R 10 ;
  • R 9 is halogen, C j -Cg alkyl, C j -Cg alkoxy, C j -Cg haloalkyl or C j -Cg haloalkoxy;
  • R 10 is halogen, C r C 6 alkyl, C r C 6 alkoxy, C r C 6 haloalkyl or
  • G is N
  • Z is phenyl, pyridinyl, thiazolyl or thiadiazolyl, each optionally substituted with R 9 and optionally substituted with one or more R 10 ;
  • R 8 is CH 3 ;
  • R 9 is halogen, Cj-Cg alkyl, C j -Cg alkoxy, C j -Cg haloalkyl or
  • R 10 is halogen, C r C 6 alkyl, C r C 6 alkoxy, C r C 6 haloalkyl or Cj-Cg haloalkoxy; provided that i) when X is OMe, R 3 is CH 3 and R 4 is H, then Z is other than 3-(trifluoromethyl)phenyl; and ii) when X is OMe, R 3 is H and R 4 is CH 3 , then Z is other than 3-(trifluoromethyl)phenyl. Preferred 4.
  • T is T 1 ;
  • A is N;
  • G is N;
  • Z is thienyl optionally substituted with R 9 and optionally substituted with one or more R 10 ;
  • R 8 is CH 3 ;
  • R 9 is halogen or C ⁇ -C 3 alkyl; and R 10 is halogen or C r C 3 alkyl.
  • This invention also relates to fungicidal compositions comprising fungicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • the preferred compositions of the present invention are those which comprise the above preferred compounds.
  • This invention also relates to a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of the compounds of the invention (e.g., as a composition described herein).
  • the preferred methods of use are those involving the above preferred compounds.
  • This invention also relates to arthropodicidal compositions comprising arthropodicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • This invention also relates to a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of the compounds of the invention (e.g., as a composition described herein).
  • the preferred methods of use are those involving the above preferred compounds.
  • T T 1
  • G G is N
  • A is N and the floating double bond is attached to A
  • W is O
  • X is OCH 3
  • R 8 is H, C r C 3 alkyl, C r C 3 haloalkyl, C 2 -C 3 alkenyl, C -C 3 alkynyl, cyclopropyl or cyano
  • Z is phenyl optionally substituted with R 9 and optionally substituted with R 10
  • R 9 is H, halogen, -C alkyl, C r C 6 haloalkyl, C j -Cg alkoxy, C r C 6 haloalkoxy, C -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl, C
  • R 9 is H, halogen, C j -C 6 alkyl, C j -Cg haloalkyl, Cj-Cg alkoxy, Cj-Cg haloalkoxy, C -C 6 alkenyl, C -Cg haloalkenyl, C 2 -C 6 alkynyl,
  • Compounds 1-10 and 40 in Index Table A are Compounds 1-10 and 40 in Index Table A. Also of note are compounds of Formula I other than Compounds 1-10 and 40 in Index Table A (e.g., Compounds 11-39 and 41-71 in Index Table A and Compound 72 in Index Table B).
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-46.
  • the definitions of T, A, G, W, X, Y, Z, R ⁇ -R 21 , m, n, r and s in the compounds of Formulae 1-62 below are as defined above in the Summary of the Invention.
  • Compounds of Formulae Ia-Iy are various subsets of the compounds of Formula I, and all substituents for Formulae Ia-Iy are as defined above for Formula I.
  • a compound of Formula I wherein T is T 1 and R 2 is H may exist as tautomer la or lb, or both la and lb.
  • Procedures 1) to 5 describe syntheses involving construction of the heterocycle after the formation of the aryl moiety.
  • Procedure 5) describes syntheses of the aryl moiety with the T-moiety already in place.
  • Suitable solvents are selected from the group consisting of polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide; ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; and halocarbons such as dichloromethane or chloroform.
  • polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide
  • ethers such as tetrahydrofuran, dimethoxyethane, or diethyl ether
  • ketones such as
  • Use of trimethylsilyldiazomethane requires a protic cosolvent such as methanol.
  • Suitable Lewis acids include trimethylsilyl triflate and tetrafluoroboric acid.
  • the alkyl trichloroacetimidates can be prepared from the appropriate alcohol and trichloroacetonitrile as described in the literature (J. Danklmaier and H. H ⁇ nig, Synth. Commun., (1990), 10, 203).
  • a trialkyloxonium tetrafluoroborate e.g., Meerwein's salt
  • the use of trialkyloxonium salts as powerful alkylating agents is well known in the art (see U. Sch ⁇ llkopf, U. Groth, C. O.ng, Angew. Chem., Int. Ed. Engl, (1981), 10, 798).
  • Appropriate bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, pyridine, or tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine.
  • alkali metal alkoxides such as potassium tert-butoxide
  • inorganic bases such as sodium hydride and potassium carbonate
  • pyridine or tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine.
  • the nucleophiles of Formula 6 are N-substituted hydroxylamines (HO- ⁇ HR 2 ) and substituted hydrazines (H ⁇ (R 5 )- ⁇ HR 2 ). Examples of such nucleophiles are N-methylhydroxylamine and methylhydrazine.
  • Compounds of Formula lb can be prepared by reaction of nitrile esters of Formula 7 with ambident nucleophiles of Formula 6. See M. Scobie and G. Tennant, J Chem. Soc, Chem. Comm., (1994), 2451. Alkylation of lb with alkyl halides in the presence of base provides compounds of Formula lc. Alternatively, treatment of lb with alkylamines or alkoxyamines provides compounds of Formula lc.
  • W N(C j -C alkyl) or NO(C j -Cg alkyl)
  • Esters of Formula 5a can be prepared from copper (I)-catalyzed reaction of malonate esters with substituted iodobenzenes of Formula 8 according to methods adapted from A. Osuka, T. Kobayashi and H. Suzuki, Synthesis , (1983), 67, and illustrated in Scheme 3.
  • R C j -C 4 alkyl
  • malonate esters of Formula 5a can be prepared by treating phenyl acetic acid esters of Formula 9a with a dialkyl carbonate or alkyl chloro formate in the presence of a suitable base such as, but not limited to, sodium metal and sodium hydride (Scheme 4).
  • a suitable base such as, but not limited to, sodium metal and sodium hydride (Scheme 4).
  • Nitrile esters of Formula 7 can be prepared similarly from compounds of Formula 10.
  • R C j -C 4 alkyl
  • Esters of Formula 9a (compounds of Formula 9 wherein E 1 is OR) can be prepared from acid-catalyzed alcoholysis of phenyl acetonitriles of Formula 10 or by esterification of phenyl acetic acids of Formula 11 as illustrated in Scheme 5 (see Org. Synth, Coll. Vol. I, (1941), 270).
  • Phenyl acetic acid esters of Formula 9b (compounds of Formula 9a wherein Y is Y 1 ) can also be prepared by copper (I)-catalyzed condensation of phenyl halides of Formula 12 with compounds of Formula 13 as described in EP-A-307,103 and illustrated below in Scheme 6.
  • Compounds of Formula 12 can be prepared by the Arndt-Eistert synthesis starting from benzoic acids of Formula 14 as illustrated in Scheme 7, (see F. Arndt, B. Eistert, Ber. 68, 200 (1935); T. Aoyama, T. Shioiri, Tetrahedron Letters 11, 4461 (1980)).
  • a halogenating agent such as thionyl chloride
  • an alkylating agent such as diazomethane
  • Compounds of Formula 14 can be prepared from nitrobenzoic acids of Formula 15 by a modification of the Sandmayer Reaction as taught in S. Kanoh, H. Muramoto, N. Kobayashi, M. Motoi and H. Suda, Bull. Chem. Soc. Jpn. 60, 3659 (1987) and M. P. Doyle, J Org. Chem. 41, 2426 (1977) (Scheme 8).
  • the compound can be prepared by nitration and reduction of commercially available 2,5-dimethylbenzoic acid as taught in A.N. Fugiwara, E. M. Acton, Can. J. Chem. 48, 1346 (1970).
  • esters of Formula 9c can also be prepared by forming the Y 2 bridge using conventional nucleophilic substitution chemistry (Scheme 9). Displacement of an appropriate leaving group (Lg) in electrophiles of Formula 17 or 18 with a nucleophilic ester of Formula 16 affords compounds of Formula 9c.
  • a base for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compound of Formula 16.
  • R C j -C 4 alkyl
  • Lg Br, Cl, I, OS0 2 CH 3 , OS0 2 (4-Me-Ph)
  • Compounds of Formula 16 can be prepared from compounds of Formula 12 by methods taught in Chem. Pharm. Bull 33 (12), 5184 (1985) or J. Org. Chem. 53 (2) 439, (1988). For example treatment of compounds of Formula 12 with a metal hydroxide, such as sodium hydroxide, in a polar protic solvent in the presence of a metal species such as copper yields compound 16a (compounds of Formula 16 where R 14 is OH).
  • Compounds of Formula 16b (compounds of Formula 16 where R 14 is CH 2 OH or CH 2 SH) can be prepared by metal-halogen exchange in compounds of Formula 12 followed by quenching with the appropriate electrophile.
  • reducing agents sodium borohydride (NaBH 4 ), sodium cyanoborohydride (NaCNBH 4 ) and diisobutylaluminum hydride (DIBAL-H) (Scheme 10).
  • Suitable inert solvents are methanol, ethanol, methylene chloride and THF, (see M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons: New York, (1986)).
  • esters of Formula 9d can also be prepared by forming the Y 3 bridge from substituted hydroxylamines 16d and carbonyl compounds 19.
  • the hydroxylamines 16d are in turn prepared from esters 16c.
  • Compounds of Formula 16c where the Lg is Br, Cl, I, OSO 2 CH 3 or OSO 2 (4-Me-Ph) can be prepared from compounds of Formula 16b, (see March, J. Advanced Organic Chemistry, 3rd ed., John Wiley: New York, (1985). This method has been described in EP-A-600,835 and is illustrated in Scheme 11.
  • Compounds of Formula 20a can be prepared from compounds of Formula Id (compounds of Formula 1 wherein X 1 is OH) by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding ⁇ -halo-substituted derivatives (Scheme 13).
  • halogenating agents such as thionyl chloride or phosphorus oxybromide
  • compounds of Formula Id can be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methane sulfonyl chloride, />-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -alkylsulfonate of Formula 20b.
  • the reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine).
  • sulfonyl compounds of Formula 20c can be prepared by oxidation of the corresponding thio compound of Formula 21 using well-known methods for the oxidation of sulfur (see Schrenk, K. in The Chemistry ofSulphones and Sulphoxides; Patai, S. et al., Eds.; Wiley: New York, (1988)).
  • Suitable oxidizing reagents include met ⁇ -chloro-peroxybenzoic acid, hydrogen peroxide and Oxone® (KHSO 5 ).
  • halo-compounds of Formula 20d can be prepared from hydrazides of Formula 22 as illustrated in Scheme 15.
  • the compound of Formula 22 is treated with excess of a thionyl halide such as thionyl chloride.
  • the product formed first is the ring-closed compound of Formula 23 which can be isolated or converted in situ to the compound of Formula 20d; see P. Molina, A. Tarraga, A. Espinosa, Synthesis, (1989), 923 for a description of this process.
  • the hydrazides of Formula 22 can be prepared as illustrated in Scheme 16. Condensation of the isocyanate of Formula 24 with the hydrazine of Formula H 2 NNR 2 R 15 in an inert solvent such as tetrahydrofuran affords the hydrazide.
  • R C j -C 4 alkyl 25a
  • Q 4 H, C j -Cg alkyl, C j -Cg alkoxy
  • the carbonylating agents can be alkyl chloroformates or dialkyl carbonates. Some of these carbonylating reactions may require the addition of a base to effect reaction.
  • Appropriate bases include alkali metal alkoxides such as potassium tert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, pyridine, or tertiary amines such as triethylamine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or triethylenediamine.
  • Suitable solvents include polar aprotic solvents such as acetonitrile, dimethylformamide, or dimethyl sulfoxide; ethers such as tetrahydrofuran, dimethoxyethane or diethyl ether; ketones such as acetone or 2-butanone; hydrocarbons such as toluene or benzene; or halocarbons such as dichloromethane or chloroform.
  • the reaction temperature can vary between 0 °C and 150 °C and the reaction time can be from 1 to 72 hours depending on the choice of base, solvent, temperature, and substrates.
  • Q 1 and Q 2 are independently Cl, OCCl 3 , 0(C j -C 4 alkyl), 1 -imidazolyl, 1,2,4-triazolyl
  • N-Amino-ureas of Formula 26 can be prepared as illustrated in Scheme 20.
  • Treatment of an aniline of Formula 27 with phosgene, thiophosgene, NN'-carbonyldiimidazole, or NN'-thiocarbonyldiimidazole produces the isocyanate or isothiocyanate of Formula 28.
  • a base can be added for reactions with phosgene or thiophosgene.
  • Subsequent treatment of the iso(thio)cyanate with an R 2 -substituted hydrazine produces the N-amino-urea of Formula 26.
  • Compounds of Formula 29 can be prepared by contacting benzyl halides, mesylates or tosylates of Formula 30 with various nucleophiles (Scheme 22).
  • the appropriate alcohol or thiol is treated with a base, for example sodium hydride, to form the corresponding alkoxide or thioalkoxide which acts as the nucleophile.
  • Lg Br, Cl, I, OS0 CH 3 , OS0 2 (4-Me-Ph)
  • Formula 30a (compounds of Formula 30 where the Lg group has been replaced with OH) by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding ⁇ -halo-substituted derivatives (Scheme 23).
  • Compounds of Formula 30a can also be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methane sulfonyl chloride, />-toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -alkylsulfonate of Formula 30.
  • the reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine).
  • Formula 1 f compounds can be prepared by reaction of Formula 28 iso(thio)cyanates or Formula 28a carbodiimides with Formula 35 esters. As described above, base may be added to accelerate the reaction and subsequent cyclization to Formula If compounds.
  • Carbodiimides 28a can be prepared as shown in Scheme 25, starting with compounds of Formula 28 and forming compounds of Formula 34 which are dehydrated to give compounds of Formula 28a.
  • the (thio)ureas or amidines of Formula 32 can be prepared by either of the methods illustrated in Scheme 26.
  • an iso(thio)cyanate of Formula 28 or carbodiimide of Formula 28a can be condensed with an amine of Formula R 2 -NH 2 to form the urea or amidine.
  • the anilines and iso(thio)cyanates of Formulae 27 and 28, respectively, are commercially available or prepared by well-known methods.
  • isothiocyanates can be prepared by methods described in J. Heterocycl. Chem. , (1990), 17, 407.
  • Isocyanates can be prepared as described in March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), pp 944, 1166.
  • Compounds of Formula Im (compounds of Formula I where T is T 1 , X is OR 1 , R 1 is CH 3 , R 2 is CH 3 , W is O, A is N, G is N, Y 5 is -O-, -OCH 2 - or -SCHR 1 ] -) can be prepared by forming the Y 5 bridge using conventional nucleophilic substitution chemistry (Scheme 30). Displacement of an appropriate leaving group (Lg) in electrophiles of Formula 17 or 18 with nucleophilic compounds of Formula 36 affords compounds of Formula Im.
  • a base for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compounds of Formula 37.
  • an additional substituent on Z which activates the leaving group (Lg) can be advantageous (e.g., when Lg-Z is 2-chloro-3 -nitro thiophene, the activating nitro group can be removed after coupling by reduction to the amine followed by diazotization and reduction to provide compounds of Formula Im).
  • Benzyl halides of Formula 38 can be prepared by radical halogenation of the corresponding alkyl compound of Formula 39a, see WO 96/38425. Benzyl halides can also be prepared by the acidic cleavage of the corresponding methyl ether of Formula 39b under conditions which provide the halide, see Scheme 31. Methods for preparing the corresponding compounds of Formula 38 wherein the T 1 group has been replaced by T 2 are described in WO 94/05620. Methods for preparing the corresponding compounds of Formula 38 wherein the T 1 group has been replaced by T 3 are described in EP-A-254,426, EP-A-299,694 and AU-A-55899/90.
  • compounds of Formula 38 can be prepared from the corresponding alcohol of Formula 40 by reaction with halogenating agents such as thionyl chloride or phosphorus oxybromide to form the corresponding ⁇ -halo-substituted derivatives.
  • compounds of Formula 40 can be treated with an alkylsulfonyl halide or haloalkylsulfonyl anhydride, such as methane sulfonyl chloride, / toluenesulfonyl chloride, and trifluoromethanesulfonyl anhydride, to form the corresponding ⁇ -alkylsulfonate of Formula 41.
  • the reaction with the sulfonyl halides may be performed in the presence of a suitable base (e.g., triethylamine) see Scheme 32.
  • Compounds of Formula 40 can be prepared by reducing esters of Formula 44 or aldehydes of Formula 43 with an appropriate reducing agent, (M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons pp. 147-160, (1986)).
  • an appropriate reducing agent M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons pp. 147-160, (1986)
  • DIBAL-H diisobutylaluminum hydride
  • Compounds of Formula 43 can be reduced with sodium borohydride in a protic solvent such as methanol or ethanol, Scheme 34.
  • Esters of Formula 44 can be prepared from anthranilic acid esters of Formula 45 according to the procedures described in Scheme 35.
  • Esters 45 can be prepared from readily accessible anthranilic acids by esterification techniques well known in the art.
  • a formaldehyde equivalent i.e., dimethylformamide or methyl chloro formate
  • compounds of Formula 48 can be prepared from compounds of Formula 46 by metallation using an alkyllithium followed by quenching with a trialkoxy borane, (Scheme 38), see Organic Synthesis via Boranes; Wiley: New York, (1975).
  • R Cj-C 4 alkyl
  • Compounds of Formula 54 are prepared by nitration of commercially available 2,5-dimethylphenol 53 as taught in M. Quertani, P. Girard and H. B. Kagan, Tetrahedron Letters, 13, 4315 (1982), Scheme 40.
  • R 0 P(CgH 5 ) 3 + (Cl. Br or l)
  • R 0 P(O(Cj-C4 alkyl)) 2
  • the olefin of Formula Ip can also be prepared by reversing the reactivity of the reactants in the Wittig or Horner-Emmons condensation.
  • 2-alkylphenyl derivatives of Formula 56 can be converted into the corresponding dibromo -compounds of Formula 57a as illustrated in Scheme 42 (see Synthesis, (1988), 330).
  • the dibromo- compounds can be hydrolyzed to the carbonyl compounds of Formula 57b, which in turn can be condensed with a phosphorus-containing nucleophile of Formula 58 or 59 to afford the olefins of Formula Ip.
  • NBS jV-bromosuccinimide 57b
  • Carbamates of Formula lu can be prepared by reacting benzyl alcohols of Formula 61 with iso(thio)cyanates of Formula 62 (Scheme 44).
  • a base such as triethylamine can be added to catalyze the reaction.
  • Compounds of Formula Iw may be prepared by methods described in EP-A- 178,826, EP-A-341,845 and EP-A-464,381.
  • a triarylbismuth compound or a substituted phenylboronic acid in the presence of cupric acetate and a tertiary amine such as pyridine or triethylamine as illustrated in Scheme 46.
  • organobismuth reagents in the preparation of diary 1 ethers is well known in the art (see Tetrahedron Lett., (1986), 17, 3619, and Tetrahedron Lett., (1987), 18, 887).
  • Boronic acids are well known in the literature (see Ada Chem. Scand. 1993, 47, 221 and references therein).
  • Step A Preparation of N-(2-methoxy-6-methylphenyl)-2,2- dimethylhvdrazinecarboxamide
  • phosgene 108 g, 1.09 moles
  • 2-methoxy-6-methylaniline 125.0 g, 911 mmol
  • Step B Preparation of 5-chloro-2.4-dihvdro-4-(2-methoxy-6-methylphenyl)-2- methyl-3H-l,2,4-triazol-3-one
  • the title compound of Step A (100.0 g, 447.9 mmol) was suspended in ethyl acetate (1 L) and added dropwise, via mechanical pump, over 3.5 h to a stirring solution of phosgene (177 g, 1.79 moles) in ethyl acetate (1.5 L) which was heated at reflux. After the addition was complete, the mixture was heated at reflux for a further 3 h, cooled to room temperature and stirred overnight.
  • Step D Preparation of 2.4-dihydro-4-(2-hvdroxy-6-methylphenyl)-5-methoxy-2- methyl-3H- 2.4-triazol-3-one
  • tetrahydrofuran 1.5 L
  • Step E Preparation of 2.4-dihydro-5-methoxy-2-methyl-4-[6-methyl-2-r3- ftrifluoromethyl phenoxy]phenyll-3H- 1.2.4-triazol-3-one
  • 2,4-dihydro-4-(2-hydroxy-6-methylphenyl)-5-methoxy-2-methyl-3H- l,2,4-triazol-3-one (0.50 g, 2.13 mmol)
  • methylene chloride 15 mL
  • Step B 2,4-dihydro-5-methoxy-2-methyl-4- 2-methyl-6-( ' 2-thienyloxy phenyll-3H-
  • 6-OCHF 2 -2-pyridinyl 3-Et-phenyl 1-naphthalenyl 1 ,2,3 ,4-tetrahydro-2-naphthalenyl
  • 6-(2,2,2-trifluoroethoxy)-4- 4-(2,2,2-trifluoroethoxy)-2- pyrimidinyl pyrimidinyl pyrimidinyl 3,5-diMe-phenyl 2-naphthalenyl 5,6,7,8-tetrahydro-2-naphthalenyl) 4-OCF 3 -phenyl 3-NBu-phenyl 4-/-Bu-phenyl 6-(2,2,2-trifluoroethoxy)-2- 3-SCF 3 -phenyl 4-SCF 3 -phenyl pyrazinyl 4-CF 3 -6-Me-2-pyridinyl 4 ,6-diMe-2-pyridiny 1 3,5-di(CF 3 )-phenyl 3-(CH 3 C ⁇ C)-phenyl Y -CH 2 0-
  • Y -OCH 2 - Z 2-Me-phenyl 2,5-diMe-phenyl 3-CF 3 -phenyl 4-CF -phenyl 4-Me-phenyl 4-?-Bu-phenyl 3-Cl-phenyl 4-Cl-phenyl 2-Me-5-Cl-phenyl 3-?-Bu-phenyl 2-naphthalenyl 1 -naphthalenyl 3 -pyridinyl 4-pyridinyl 6-Me-2-pyridinyl 5,6,7,8-tetrahydro-2-naphthalenyl
  • 6-(2,2,2-trifluoroethoxy)-4- 4-(2,2,2-trifluoroethoxy)-2- pyrimidinyl pyrimidinyl pyrimidinyl 3,5-diMe-phenyl 2-naphthalenyl 5,6,7, 8-tetrahydro-2-naphthalenyl) 4-OCF 3 -phenyl 3-Z-Bu-phenyl 4-/-Bu-phenyl 6-(2,2,2-trifluoroethoxy)-2- 3-SCF 3 -phenyl 4-SCF 3 -phenyl pyrazinyl 4-CF 3 -6-Me-2-pyridiny 1 4,6-diMe-2-pyridinyl 3,5-di(CF 3 )-phenyl 3-(CH 3 C ⁇ C)-phenyl Y -CH 2 0-
  • 6-(2,2,2-trifluoroethoxy)-4- 4-(2,2,2-trifluoroethoxy)-2- pyrimidinyl pyrimidinyl pyrimidinyl 3,5-diMe-phenyl 2-naphthalenyl 5,6,7,8-tetrahydro-2-naphthalenyl 4-OCF 3 -phenyl 3-t-Bu-phenyl 4-t-Bu-phenyl 6-(2,2,2-trifluoroethoxy)-2- 3-SCF 3 -phenyl 4-SCF 3 -phenyl pyrazinyl 4-CF3-6-Me-2 -pyridinyl 4,6-diMe-2-pyridinyl 3,5-di(CF 3 )-phenyl Y -CH 2 0-

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KR20230004757A (ko) * 2020-04-28 2023-01-06 바스프 에스이 Qo 억제제 IV 에 대한 내성을 부여하는 미토콘드리아 시토크롬 b 단백질에서 아미노산 치환 F129L 을 함유하는 식물병원성 진균을 퇴치하기 위한 스트로빌루린 유형 화합물의 용도
CN115484820A (zh) * 2020-04-28 2022-12-16 巴斯夫欧洲公司 嗜球果伞素类型化合物防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂I的耐受性的氨基酸替代F129L的植物病原性真菌的用途
EP3903583A1 (de) 2020-04-28 2021-11-03 Basf Se Verwendung von verbindungen vom strobilurintyp zur bekämpfung von phytopathogenen pilzen, die eine aminosäuresubstitution f129l in dem mitochondrialen cytochrom-b-protein enthalten, das resistenz gegenüber qo-inhibitoren iii verleiht
IL297583A (en) 2020-04-28 2022-12-01 Basf Se Use of strobilurin type compounds to control phytopathogenic fungi containing amino acid transformation f129l in mitochondrial cytochrome b protein conferring resistance to ii qo inhibitors
EP3903582A1 (de) 2020-04-28 2021-11-03 Basf Se Verwendung von verbindungen vom strobilurintyp zur bekämpfung von phytopathogenen pilzen, die eine aminosäuresubstitution f129l in dem mitochondrialen cytochrom-b-protein enthalten, das resistenz gegenüber qo-inhibitoren ii verleiht
EP4142495A1 (de) * 2020-04-28 2023-03-08 Basf Se Verwendung von verbindungen vom strobilurintyp zur bekämpfung von phytopathogenen pilzen, die eine aminosäuresubstitution f129l in dem mitochondrialen cytochrom-b-protein enthalten, das resistenz gegenüber qo-inhibitoren iii verleiht
EP3903584A1 (de) 2020-04-28 2021-11-03 Basf Se Verwendung von verbindungen vom strobilurintyp zur bekämpfung von phytopathogenen pilzen, die eine aminosäuresubstitution f129l in dem mitochondrialen cytochrom-b-protein enthalten, das resistenz gegenüber qo-inhibitoren iv verleiht
EP3939961A1 (de) 2020-07-16 2022-01-19 Basf Se Strobilurintyp und deren verwendung zur bekämpfung von phytopathogenen pilzen
EP3970494A1 (de) 2020-09-21 2022-03-23 Basf Se Verwendung von verbindungen vom strobilurintyp zur bekämpfung von phytopathogenen pilzen, die eine aminosäuresubstitution f129l in dem mitochondrialen cytochrom-b-protein enthalten, das resistenz gegenüber qo-inhibitoren viii verleiht
US20230357152A1 (en) 2020-08-11 2023-11-09 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors viii
WO2023072671A1 (en) 2021-10-28 2023-05-04 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ix
WO2023072670A1 (en) 2021-10-28 2023-05-04 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors x
WO2023072672A1 (en) 2021-10-28 2023-05-04 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors xi
EP4361126A1 (de) 2022-10-24 2024-05-01 Basf Se Verwendung von strobilurin-derivaten zur bekämpfung von phytopathogenen pilzen mit aminosäuresubstitution f129l

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AU5463398A (en) 1998-06-22
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JP2001506984A (ja) 2001-05-29
KR20000057254A (ko) 2000-09-15
CZ184599A3 (cs) 1999-09-15

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