WO1999018102A1 - Amides cycliques fongicides et arthropodicides - Google Patents

Amides cycliques fongicides et arthropodicides Download PDF

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Publication number
WO1999018102A1
WO1999018102A1 PCT/US1998/020269 US9820269W WO9918102A1 WO 1999018102 A1 WO1999018102 A1 WO 1999018102A1 US 9820269 W US9820269 W US 9820269W WO 9918102 A1 WO9918102 A1 WO 9918102A1
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Prior art keywords
optionally substituted
alkyl
phenyl
haloalkyl
cycloalkyl
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PCT/US1998/020269
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English (en)
Inventor
David Alan Clark
David Walter Piotrowski
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E.I. Du Pont De Nemours And Company
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Priority to AU96707/98A priority Critical patent/AU9670798A/en
Publication of WO1999018102A1 publication Critical patent/WO1999018102A1/fr

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    • 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
    • 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
    • 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

Definitions

  • This invention relates to certain fungicidal and arthropodicidal cyclic amides including all geometric and stereoisomers, 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.
  • This invention is directed to compounds of Formula I, including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use as fungicides and arthropodicides:
  • E is selected from (i) an optionally substituted 1,2-phenylene, (ii) an optionally substituted naphthalene ring, provided that when G and Y are attached to the same ring, then G and Y are attached to adjacent ring members and (iii) an optionally substituted 5 to 8-membered monocyclic aromatic heterocyclic ring system containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that the heterocyclic ring system contains no more than 4 nitrogens, no more than 1 oxygen, and no more than 1 sulfur;
  • A is O, S- N- NRS or CR 11 ;
  • G is C or N; provided that when G is C, then A is O, S or NR 5 and the floating double bond is attached to G; and when G is N, then A is N or CR 1 1 and the floating double bond is attached to A; W is O or S;
  • X is H, OR 1 , SCO ⁇ R 1 , halogen, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 cycloalkyl or cyano;
  • R 1 is C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 alkynyl,
  • R 2 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl,
  • R 5 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl,
  • YZ is a group consisting of (a) 3 or more atoms independently selected from the group C, N, O, S, Si and Ge, provided that at least 3 of said atoms are C, and
  • R 1 ' is H, halogen, C r C 6 alkyl, C r C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, 2 -C ⁇ alkynyl, C 2 -C 6 haloalkynyl or C3-C6 cycloalkyl; and m is 0, 1 or 2.
  • alkyl used alone or in compound words such as “alkylthio”, “alkylthioalkyl”, “haloalkylthio”, “alkylsulfinyl”, “haloalkylsulfinyl”, “alkylsulfonyl”, “haloalkylsulfonyl” and the like includes straight-chain or branched alkyl such as methyl, ethyl, /2-propyl, z ' -propyl, or the different butyl, pentyl or hexyl 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.
  • alkenyl used in compound words such as “alkenyloxy”, “alkenylthio”, “haloalkenyl”, “haloalkenyloxy” and “haloalkenylthio” is defined analogously.
  • 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.
  • alkynyl used in compound words such as “alkoxyalkynyl", “alkynyloxy”, “haloalkynyl” and “haloalkynyloxy” is defined analogously.
  • Alkoxy includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • alkoxy when used in compound words such as “alkoxyalkoxy”, “alkoxyalkyl”, “alkoxycarbonyl” and “alkylthioalkoxy” is defined analogously.
  • alkoxyalkyl include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , (CH 3 ) 2 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 and other alkoxy moieties bonded to straight-chain or branched alkyl groups.
  • alkoxyalkoxy examples include CH3OCH 2 O, CH3OCH 2 CH 2 O and other alkoxy moieties bonded to alkoxy groups.
  • Alkynyloxy includes straight-chain or branched alkynyloxy moieties.
  • alkynyloxy examples include HC ⁇ CCH 2 O, CH 3 C ⁇ CCH 2 O and CH 3 C ⁇ CCH 2 CH 2 O.
  • 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.
  • alkylthioalkyl examples include CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , (CH 3 ) 2 CH 2 CH 2 SCH 2 , CH 3 SCH(CH 3 )CH 2 and other alkylthio moieties bonded to alkyl groups.
  • alkylthioalkoxy examples include CH 3 SCH 2 CH 2 O and other alkylthio moieties bonded to alkoxy groups.
  • alkylthioalkylthio examples include CH 3 SCH 2 CH S and other alkylthio moieties bonded to alkylthio groups.
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • Cycloalkenyl includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1 ,4-cyclohexadienyl.
  • Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups.
  • Trialkylsilylalkoxyalkoxy denotes trialkylsilylalkoxy substitution on alkoxy.
  • Examples of “trialkylsilylalkoxyalkoxy” include (CH 3 ) 3 SiCH 2 CH 2 OCH 2 O.
  • halogen either alone or as “halo” in compound words such as "haloalkyl”, “haloalkenyl”, “haloalkenyloxy”, “haloalkynyl”, “haloalkynyloxy”, “haloalkoxy”, “haloalkoxyalkyl”, “haloalkylthio”, “haloalkenylthio”, haloalkylsulfinyl", and “haloalkylsulfonyl” 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.
  • haloalkyl examples include F 3 C, C1CH 2 , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkynyloxy examples include ClCH 2 C ⁇ CCH O.
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • haloalkoxyalkyl examples include CF 3 OCH 2 CH 2 , CCl 3 CH 2 OCH 2 , HCF 2 CH 2 CH 2 OCH 2 and CF 3 CH 2 OCH 2 CH 2 .
  • haloalkylthio examples include CC1 3 S, CF 3 S, CHF 2 S, CC1 3 CH 2 S and C1CH 2 CH 2 CH 2 S.
  • haloalkylsulfinyl examples include CCl 3 S(O), CF 3 S(O), CHF 2 S(O), CCl 3 CH 2 S(O) and ClCH 2 CH 2 CH 2 S(O).
  • haloalkylsulfonyl examples include CCl 3 S(O) 2 , CF 3 S(O) 2 , CHF 2 S(O) 2 , CCl 3 CH 2 S(O) 2 and ClCH 2 CH 2 CH 2 S(O) 2 .
  • the total number of carbon atoms in a substituent group is indicated by the "Cj-C j " prefix where i and j are numbers from 1 to 10.
  • C1-C3 alkoxy designates methoxy through propyloxy.
  • aromatic ring system(s) denotes fully unsaturated carbocycles and heterocycles in which the polycyclic ring system is aromatic (where aromatic indicates that the H ⁇ ckel rule is satisfied for the ring system).
  • aromatic carbocyclic ring system(s) includes carbocycles in which at least one ring of a fused bicyclic ring system is aromatic (where aromatic indicates that the H ⁇ ckel rule is satisfied).
  • nonaromatic ring system(s) denotes fully saturated carbocycles and heterocycles as well as partially or fully unsaturated carbocycles and heterocycles where the H ⁇ ckel rule is not satisfied by any of the rings in the ring system. Examples include 2,3-dihydro-lH-indenyl and 3,4-dihydro-2H-l-benzopyranyl.
  • aromatic heterocyclic ring system includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the ⁇ ckel rule is satisfied).
  • aromatic heterocyclic ring systems include 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 it is furanyl, it can be 2-furanyl or 3-furanyl, for pyrrolyl, the aromatic heterocyclic ring is l-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.
  • nonaromatic heterocyclic ring system(s) denotes fully saturated heterocycles as well as partially or fully unsaturated heterocycles where the ⁇ ckel rule is not satisfied by any of the rings in the ring system. Examples of “nonaromatic heterocyclic ring systems” include 4-morpholinyl.
  • the heterocyclic ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides.
  • tertiary amines can form N-oxides.
  • N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as t-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethydioxirane
  • stereoisomers of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers (e.g., syn and anti 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.
  • Compounds of Formula I above including all geometric and stereoisomers, and N-oxides and agriculturally suitable salts thereof, wherein E is selected from: i) 1,2-phenylene optionally substituted with R 3 or both R 3 and R 4 ; ii) a naphthalene ring optionally substituted with R 3 or both R 3 and R 4 , provided that when G and Y are attached to the same ring, then G and Y are attached to adjacent ring members; iii) a ring system selected from 5 to 8-membered monocyclic aromatic heterocyclic ring systems, each heterocyclic ring system containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 1 oxygen, and no more than 1 sulfur, each aromatic heterocyclic ring system optionally substituted with R 3 or both R 3 and R 4 ; R 3
  • Z is selected from i) C 3 -Cg cycloalkyl, C 3 -Cg cycloalkenyl and phenyl, each optionally substituted with one or more R 10 ; and ii) a ring system selected from 3 to 14-membered monocyclic, fused bicyclic and fused tricyclic nonaromatic heterocyclic ring systems and 5 to 14-membered monocyclic, fused bicyclic and fused tricyclic aromatic heterocyclic ring systems, each heterocyclic ring system containing 1 to 6 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 4 nitrogens, no more than 2 oxygens, and no more than 2 sulfurs, each nonaromatic or aromatic heterocyclic ring system optionally substituted with one or more R 10 ; R 8 is halogen, C r C 6 alkyl, C r C 6 haloalkyl, C r C 6 alkoxy,
  • C Cg haloalkoxy C 2 -Cg alkenyl, C -C 6 haloalkenyl, C 2 -C 6 alkynyl, C r C 6 alkylthio, C r C 6 haloalkylthio, C r C 6 alkylsulfinyl, C r C 6 alkylsulfonyl, C 3 -C 6 cycloalkyl, C3-C 6 alkenyloxy, CO 2 (C r Cg alkyl), NH(C r C 6 alkyl), N(C r C 6 alkyl) 2 , cyano, nitro, Si(R 5 ) 3 or Ge(R 5 ) 3 ;
  • R 12 and R 16 along with the nitrogen atom to which said groups are attached can be taken together as a 3- to 7-membered monocyclic ring system which is optionally substituted with R 21 and optionally includes one Q as a ring member;
  • R 17 is C r C 6 alkyl; C 3 -C 6 cycloalkyl; C r C 6 haloalkyl; C 2 -C 6 alkenyl;
  • R 19 and R 20 are each independently halogen; C ⁇ -C 4 alkyl; C 3 -Cg cycloalkyl; C ⁇ -C haloalkyl; C -Cg alkenyl; C 2 -Cg haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C 2 -C 6 alkoxyalkyl; C 2 -C 6 alkylthioalkyl; C 3 -C 6 alkoxyalkynyl; C ⁇ -C j o tetrahydropyranyloxyalkynyl; phenylmethoxymethyl; C j -C 4 alkoxy; C ⁇ -C 4 haloalkoxy; C3-C 6 alkenyloxy; C 3 -C 6 haloalkenyloxy; C 3 -C 6 alkynyloxy; C 3 -C 6 haloalkynyloxy; C -C
  • S(O) 2 OR 23 S(O) 2 N(R 2 ) 2 ; OS(O) 2 R 24 ; N(R 23 )S(O) 2 R 24 ; or phenyl, phenoxy, phenylmethyl, phenylmethoxy, phenylsulfonyl, phenylethynyl or pyridinylethynyl, each aromatic ring optionally substituted with one or more R 10 ;
  • R 21 is C1-C3 alkyl or C r C 3 haloalkyl;
  • R 22 is H, C j -Cg alkyl, C j -Cg haloalkyl or phenyl optionally substituted with
  • each R 23 is independently H, C Cg alkyl, C Cg haloalkyl, C 2 -Cg alkenyl,
  • each R 24 is independently C j -Cg alkyl, C j -C haloalkyl, C 2 -Cg alkenyl,
  • each R 25 is independently C j -C 4 alkyl, C ⁇ -C 4 haloalkyl, C 2 -C 4 alkenyl,
  • R 26 is C,-Cg alkyl, C r C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl,
  • R 27 is C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl,
  • E is 1 ,2-phenylene optionally substituted with one or two methyl groups
  • X is OR 1 ;
  • Z is selected from phenyl and 5- to 6-membered monocyclic aromatic heterocyclic ring systems containing 1 to 3 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, provided that each heterocyclic ring system contains no more than 3 nitrogens, no more than 1 oxygen, and no more than 1 sulfur, each phenyl or aromatic heterocyclic ring system optionally substituted
  • Z is phenyl, thienyl, thiazolyl, thiadiazolyl, pyridinyl or pyrimidinyl, each optionally substituted with one or more R 10 ;
  • R 1 is CH 3 ;
  • R 2 is CH 3 ;
  • R 7 is CH 3 ;
  • R 12 is C r Cg alkyl; C 3 -C 6 cycloalkyl; C r C 6 haloalkyl; C 2 -C 6 alkoxyalkyl;
  • R 13 and R 14 are each independently selected from the group Ci-Cg alkyl, Cj-Cg haloalkyl, phenyl optionally substituted with one to three R 10 or phenylmethyl optionally substituted with one to three R 10 ;
  • R 15 is H or CH 3 ;
  • 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.
  • 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).
  • 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.
  • the preferred compositions of the present invention are those which comprise the above preferred compounds.
  • 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.
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-6.
  • the definitions of A, E, G, T, T 1 , U, W, X, Y, Z, R 2 , R 9 , R 12 -R 18 , x, Lg and Lg 1 in the compounds of Formulae 1-9 below are as defined above in the Summary of the Invention or as defined below in the Details of the Synthesis.
  • Compounds of Formula I can be prepared by condensation of a compound U-NH 2 (Formulae 2-5) with a carbonyl compound of Formula 1 in the presence of an optional base as depicted in Scheme 1.
  • Typical solvents can be methanol, ethanol, benzene, toluene or methylene chloride.
  • Typical bases can be sodium acetate, sodium bicarbonate, triethylamine or pyridine.
  • Such reactions of hydroxylamines or hydroxylamine salts (Formula 2), hydrazines or hydrazine salts (Formula 3), amines or amine salts (Formula 4) or hydrazones (Formula 5) with carbonyl compounds are well known to one skilled in the art.
  • R 9 is -C(Rl )-NORl 7 ,
  • Scheme 2 depicts this transformation.
  • Lg is F, Cl, Br, S0 2 CH 3 , S0 2 (4-Me-Ph) Y is (CH 2 ) ⁇
  • ⁇ is O, S, orNRl5 x is 0 or 1 x is 0 or 1
  • Scheme 3 depicts this transformation.
  • Lg is F, Cl, Br, S0 2 CH 3 , S0 2 (4-Me-Ph)
  • ⁇ O. S, orNRl5
  • Y Js (CH 2 ) ⁇ x is 0 or 1 x is 0 or 1
  • Compounds of Formula 1 can be prepared by reaction of compounds of Formula 9 (Z is aromatic, alkenyl or cyclopropyl) with carbon monoxide and a suitable organometallic compound (for example aryl boronic acids) in the presence of a suitable transition metal (e.g., palladium(II) acetate) with a suitable ligand (e.g., triphenylphosphine or l,l'-bis(diphenylphosphino)ferrocene) and a suitable base (e.g.
  • a suitable transition metal e.g., palladium(II) acetate
  • a suitable ligand e.g., triphenylphosphine or l,l'-bis(diphenylphosphino)ferrocene
  • a suitable base e.g.
  • U is ORl 7 , NRl2, N(Rl 2 )(Rl6) or
  • compounds of Formula 7a can be prepared by alkylation of an oxime of Formula 7a (R 17 is H) in the presence of a base as depicted in Scheme 6. Such reactions are well known to one skilled in the art (see March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), p 359).
  • Rl 7 is other than H
  • Lg is F, O, Br, S0 CH 3 , S0 2 (4-Me-Ph) Lgl is Cl, Br, I, OS0 2 CH 3 , OS0 2 (4-Me-Ph)
  • Step A Preparation of ethyl 2-chloro-4-thiazolecarboxylate t-Butylnitrite (29 mL, 0.244 mol) was added dropwise to a suspension of ethyl 2-amino-4-thiazolecarboxylate (28.0 g, 0.163 mol) (prepared according to Dickey et al., J. Org. Chem. 1954, 20, 499) and anhydrous cupric chloride (32.8 g, 0.244 mol) in 400 mL acetonitrile. After stirring overnight, water and chloroform were added and the mixture was made acidic with 12N hydrochloric acid. The layers were separated. The aqueous layer was extracted 2 times with chloroform.
  • Step C Preparation of 4-r2-f(4-acetyl-2-thiazolyl)oxylphenyl]-2.4-dihvdro-5- methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one
  • Step D Preparation of 4-r2-IT4-r 1 -[(1.1 -dimethylethoxy iminolethyll-2- thiazolylloxylphenyll-2,4-dihydro-5-methoxy-2-methyl-3H-l,2,4-triazol-3- one
  • Step B Preparation of l-(2-chloro-4-methyl-5-thiazolyl)ethanone t-Butylnitrite (23.5 mL, 0198 mmol) was added dropwise to a suspension of l-(2-amino-4-methyl-5-thiazolyl)ethanone (19.0 g, 121.6 mmol) and anhydrous cupric chloride (26.6 g, 198 mmol) in 225 mL acetonitrile over 1 hour. After stirring at room temperature for 2 hours, water and chloroform were added and the mixture was made acidic with 12N hydrochloric acid. The layers were separated. The aqueous layer was extracted 2 times with chloroform.
  • Step D Preparation of 4-12-175-1 " 1 -IY 1 , 1 -dimethylethoxy)imino1ethyll-4-methyl-2- thiazolylloxy1phenyll-2,4-dihvdro-5-methoxy-2-methyl-3H- 2,4-triazol-3- one
  • a solution of the title compound of Step C (0.50 g, 1.4 mmol), t-butylhydroxylamine hydrochloride (0.18 g, 1.4 mmol) and sodium acetate (0.13 g, 1.5 mmol) in methanol was stirred at room temperature for 2 hours, and then heated under reflux.
  • Step B Preparation of ethyl 2-chloro-4-methyl-5-thiazolecarboxylate t-Butylnitrite (20.4 mL, 114 mmol) was added dropwise to a suspension of the title compound of Step A (21.6 g, 114 mmol) and anhydrous cupric chloride (23.0 g, 171 mmol) in 200 mL acetonitrile over 1 hour. After stirring at room temperature for 2 hours, water and chloroform were added and the mixture was made acidic with 12N hydrochloric acid. The aqueous layer was extracted twice with chloroform. The combined organic extracts were dried over MgSO 4 , filtered and concentrated.
  • the crude acid chloride (2.0 g, 10.2 mmol) was dissolved in about 30 mL methylene chloride/toluene (1 :1) and cooled to 0 °C.
  • Aluminum chloride (1.4 g, 10.5 mmol) was added in portions.
  • the reaction mixture was allowed to warm to room temperature. After 6 hours, IN hydrochloric acid was added.
  • the mixture was extracted 3 times with ethyl acetate. The combined extracts were washed 2 times with sodium carbonate solution, 1 time with water, 1 time with brine, dried over MgSO 4 , filtered and concentrated.
  • Step E Preparation of 2,4-dihvdro-5-methoxy-2-methyl-4-r2-r 4-methyl-5-(4- methylbenzovD-2-thiazolyl]oxy1phenyl ⁇ l-3H-1.2.4-triazol-3-one
  • a suspension of 2,4-dihydro-4-(2-hydoxyphenyl)-5-methoxy-2-methyl-3H-l, 2,4- triazol-3-one (0.50 g, 2.26 mmol) (prepared according to WO 97/00612), the title compound of Step D (0.50 g, 1.99 mmol) and potassium carbonate (0.50 g, 3.62 mmol) in acetonitrile was heated under reflux for 5 hours, then cooled and stirred at room temperature for 16 hours.
  • Step F Preparation of 2.4-dihvdro-5-methoxy-4-[2-[T5-rfmethoxyimino)(4- methylphenyl)methyll-4-methyl-2-thiazolylloxylphenvn-2-methyl-3H-1.2.4- triazol-3-one
  • a solution of the title compound of Step E (0.46 g, 1.05 mmol), methylhydroxylamine hydrochloride (0.26 g, 3.11 mmol) and sodium acetate (0.26 g, 3.16 mmol) in methanol was heated under reflux.
  • Step C Preparation of 5-chloro-3-[f2,4-difluorophenyl)r(tetrahvdro-2H-pyran-2- yl)oxy " lmethyl ⁇
  • triethylamine 29.4 mL, 210.8 mmol
  • Step E Preparation of 4-[2-[r3-r(2.4-difluorophenyl)hvdroxymethyl1- 1 ,2,4-thiadiazol- 5-vHoxylphenvn- 2.4-dihvdro-5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one
  • step D To a solution of the title compound of step D (0.52 g, 0.979 mmol) in ethanol (5 mL) was added /7-toluenesulfonic acid (20 mg, 0.098 mmol) and the solution stirred at ambient temperature for 3 hours before being quenched with Na ⁇ CO 3 and twice extracted with methylene chloride. The combined organic fractions were dried (MgSO 4 ) and concentrated. Purification by column chromatography (silica gel, 80% ethyl ether in petroleum ether) gave the title compound of step D as an off white solid (0.28 g).
  • Step F Preparation of 4-r2-r[3-(2.4-difluorobenzoyl)-l,2.4-thiadiazol-5- ylloxy1phenyll-2.4-dihvdro-5-methoxy-2-methyl-3H-l,2,4-triazol-3-one
  • methylene chloride 10 mL
  • activated manganese dioxide 1.09 g, 12.52 mmol
  • Step G Preparation of 4-r2-[r3-r ⁇ / 2.4-difluorophenyl)r(l.l- dimethylethoxy)imino]methyll-l,2,4-thiadiazol-5-yl]oxylphenyl1-2,4- dihvdro-5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one
  • Step B Preparation of(4-chlorophenyl)(5-chloro-l, 2 ,4-thiadiazol-3-yl)methanone
  • Step C Preparation of 4-r2-r[3-(4-chlorobenzoyl)-l,2,4-thiadiazol-5-yl]oxylphenyll-
  • Step D Preparation of 4-r2-rr3-r(4-chlorophenvnrf 1.1- dimethylethoxy iminolmethyll- 1 ,2,4-thiadiazol-5-yl] oxylphenyll-2,4- dihydro-5-methoxy-2-methyl-3H- 1 ,2.4-triazol-3-one
  • pyridine 0.055 mL, 0.68 mmol
  • 0-t-butyl hydroxylamine 85 mg
  • the vessel was sealed and pressurized with carbon monoxide to 75 psi and then heated to 80 °C for 3 h. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate, filtered through a pad of silica gel and washed twice with water and once with brine. The solution was dried over magnesium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 80% ethyl ether in petroleum ether, then ethyl ether, then ethyl acetate) to give the title compound of Step A (75 mg, 14% yield).
  • R 3 ' H.
  • R 3 ' H
  • R 3 ' R 3 or H
  • R 10 ' R 10 or H
  • R 3 ' H.
  • R 10 ' H
  • R 19 ' H
  • R 20 4-Me
  • R 17
  • R 10 Br
  • R 19 ' H
  • R 20 4-Me
  • R 17
  • R 10 ' H
  • R 19 ' H
  • R 20 4-F
  • R 17
  • R 10 Br
  • R 19 ' H
  • R 20 4-F
  • R 17
  • R 10 Me
  • R 19 ' H
  • R 20 4-F
  • R 17
  • R 20' H .
  • R 3 6-Me
  • R 18 C0 2 Me
  • R 3 6-Me
  • R 3 ' R 3 or H
  • R 19 ' R 19 or H
  • R 20 ' R 20 or H
  • R 3 ' R 3 orH
  • R 3 ' R 3 orH
  • R 3 ' R 3 or H
  • R 10 ' R 10 or H
  • R 3 ' R 3 or H
  • R 3 ' R 3 or H
  • R 10 ' R 10 or H
  • R 13 ' R 13 or H
  • R 3 ' R 3 orH
  • R 3 ' R 3 or H
  • R 10 ' R 10 or H
  • Rl 8 Me; ⁇ s ffl
  • R 3 Me
  • Rl : Me
  • Rl 8 4-Cl-Ph
  • Z Z 2
  • R 3 Me
  • RlO: Me
  • Rl 8 4-Cl-Ph
  • Z Z 3
  • R 3 Me
  • RlO: Me
  • Rl 8 4-Cl-Ph
  • Z Z 6
  • R 3 Me
  • Rl8 4-Cl-Ph
  • Z zl
  • Rl 7 Me CH 2 C ⁇ CH CH 2 CH
  • R 3 Me
  • Rl8 4-Me-Ph
  • Z Z 4
  • Rl 7 Me CH 2 C ⁇ CH CH 2 CH
  • R 18 2,4-di-F-Ph
  • Z Z 5
  • R 18 2,4-di-Cl-Ph
  • Z Z 2
  • Rl Me CH 2 C ⁇ CH CH 2 CH
  • R 3 Me
  • Rl Me
  • R i8 2,4-di-Cl-Ph
  • Z Z 2
  • Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant.
  • the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels.
  • Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, NN-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Liquid diluents include, for example, water, NN-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
  • Solutions can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • Compound 3 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Example B Granule Compound 4 10.0% attapulgite granules (low volatile matter
  • Example C Extruded Pellet Compound 11 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • Example D Emulsifiable Concentrate
  • Compound 20 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%.
  • the compounds of this invention are useful as plant disease control agents.
  • the present invention therefore further comprises a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, or to the plant seed or seedling to be protected, an effective amount of a compound of the invention or a fungicidal composition containing said compound.
  • the compounds and compositions of this invention provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes. They are effective in controlling a broad spectrum of plant diseases, particularly foliar pathogens of ornamental, vegetable, field, cereal, and fruit crops.
  • pathogens include Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Alternaria brassicae, Septoria nodorum, Septoria tritici, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera leucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerotheca fuligine
  • the compounds of this invention also exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, stem or root feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term “arthropods” includes insects, mites and nematodes) which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all pests.
  • all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order Coleoptera; eggs, immatures and adults of the Orders Hemiptera and Homoptera; eggs, larvae, nymphs and adults of the Order Acari; eggs, immatures and adults of the Orders Thysanoptera, Orthoptera and Dermaptera; eggs, immatures and adults of the Order Diptera; and eggs, juveniles and adults of the Phylum Nematoda.
  • the compounds of this invention are also active against pests of the Orders Hymenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura and Psocoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes.
  • the compounds are active against southern corn rootworm (Diabrotica undecimpunctata howard ⁇ ), aster leafhopper (Mascrosteles fascifrons), boll weevil (Anthonomus grandis), two-spotted spider mite (Tetranychus urticae), fall armyworm (Spodoptera frugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzus persicd), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noxia), English grain aphid (Sitobion avenae), tobacco budworm (Heliothis virescens), rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae), whitebacked planthopper (Sogatella furcifera), green leafhopper (Nephotettix cincticeps), brown planthopper
  • Tetranychidae including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, Panonychus citri, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis,
  • Eotetranychus banksi and Oligonychus pratensis Tenuipalpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus obovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae. See WO 90/10623 and WO 92/00673 for more detailed pest descriptions.
  • Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • insecticides such as abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorfenapyr, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, esfenvalerate, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, tau-fluvalinate, fonophos, imidacloprid, isofenphos, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene
  • insecticides such as abamectin, acep
  • Preferred for better control of plant diseases caused by fungal plant pathogens e.g., lower use rate or broader spectrum of plant pathogens controlled
  • resistance management are mixtures of a compound of this invention with a fungicide selected from the group cyprodinil, epoxiconazole, fenpropimorph, fenpropidin, flusilazole, propiconazole, quinoxyfen and tebuconazole.
  • Plant disease control is ordinarily accomplished by applying an effective amount of a compound of this invention either pre- or post-infection, to the portion of the plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing.
  • the compounds can also be applied to the seed to protect the seed and seedling.
  • rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions.
  • Foliage can normally be protected when treated at a rate of from less than 1 g/ha to 5,000 g/ha of active ingredient.
  • Seed and seedlings can normally be protected when seed is treated at a rate of from 0.1 to 10 g per kilogram of seed.
  • Arthropod pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more of the compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
  • the present invention further comprises a method for the control of foliar and soil inhabiting arthropods and nematode pests and protection of agronomic and/or nonagronomic crops, comprising applying one or more of the compounds of the invention, or compositions containing at least one such compound, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.
  • a preferred method of application is by spraying.
  • granular formulations of these compounds can be applied to the plant foliage or the soil.
  • Other methods of application include direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others.
  • the compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like.
  • the compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use.
  • a preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.
  • the rate of application required for effective control will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 kg/hectare may be sufficient or as much as 8 kg hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required.
  • control efficacy represents inhibition of arthropod development (including mortality) that causes significantly reduced feeding.
  • Cmpd No.” stands for "Compound Number”.
  • Ex. stands for "Example” and is followed by a number indicating in which example the compound is prepared.
  • the abbreviation “mp” stands for “melting point” and is reported in degrees Celsius.
  • **A/B Indicates a mixture of Isomer A and Isomer B.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention porte sur des composés de la formule (I) et sur leurs N-oxydes et leurs sels appropriés à l'agriculture. Ces composés sont utiles comme fongicides et arthropodicides. Dans la formule précitée, A, E, G, W, X, Y, Z, R2 et R9 sont tels que définis dans la demande. L'invention porte également sur des compositions contenant les composés de la formule (I), sur un procédé visant à lutter contre les maladies des végétaux provoquées par des agents pathogènes fongiques, ce procédé consistant à appliquer une quantité efficace d'un composé de la formule (I), et sur un procédé d'élimination des arthropodes qui consiste à mettre en contact les arthropodes ou leur environnement avec une quantité efficace d'un composé de la formule (I).
PCT/US1998/020269 1997-10-08 1998-09-28 Amides cycliques fongicides et arthropodicides WO1999018102A1 (fr)

Priority Applications (1)

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AU96707/98A AU9670798A (en) 1997-10-08 1998-09-28 Fungicidal and arthropodicidal cyclic amides

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US60/061.326 1997-10-08

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6489487B1 (en) 1998-08-03 2002-12-03 Sumitomo Chemical Company, Limited Triazolone derivatives, use thereof, and intermediates therefor
US8895556B2 (en) 2007-12-26 2014-11-25 Critical Outcome Technologies Inc. Compounds and method for treatment of cancer
US8987272B2 (en) 2010-04-01 2015-03-24 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
US9284275B2 (en) 2007-01-11 2016-03-15 Critical Outcome Technologies Inc. Inhibitor compounds and cancer treatment methods
CN114728951A (zh) * 2019-11-15 2022-07-08 先正达农作物保护股份公司 除草噻唑化合物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014009A1 (fr) * 1993-11-19 1995-05-26 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996026191A1 (fr) * 1995-02-24 1996-08-29 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036615A1 (fr) * 1995-05-16 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036616A1 (fr) * 1995-05-17 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036633A1 (fr) * 1995-05-17 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongiques
WO1997000612A1 (fr) * 1995-06-20 1997-01-09 E.I. Du Pont De Nemours And Company Amides cycliques arthropodicides et fongicides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995014009A1 (fr) * 1993-11-19 1995-05-26 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996026191A1 (fr) * 1995-02-24 1996-08-29 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036615A1 (fr) * 1995-05-16 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036616A1 (fr) * 1995-05-17 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongicides
WO1996036633A1 (fr) * 1995-05-17 1996-11-21 E.I. Du Pont De Nemours And Company Amides cycliques fongiques
WO1997000612A1 (fr) * 1995-06-20 1997-01-09 E.I. Du Pont De Nemours And Company Amides cycliques arthropodicides et fongicides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6489487B1 (en) 1998-08-03 2002-12-03 Sumitomo Chemical Company, Limited Triazolone derivatives, use thereof, and intermediates therefor
US9284275B2 (en) 2007-01-11 2016-03-15 Critical Outcome Technologies Inc. Inhibitor compounds and cancer treatment methods
US8895556B2 (en) 2007-12-26 2014-11-25 Critical Outcome Technologies Inc. Compounds and method for treatment of cancer
US8987272B2 (en) 2010-04-01 2015-03-24 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
US9422282B2 (en) 2010-04-01 2016-08-23 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
US9624220B2 (en) 2010-04-01 2017-04-18 Critical Outcome Technologies Inc. Compounds and method for treatment of HIV
CN114728951A (zh) * 2019-11-15 2022-07-08 先正达农作物保护股份公司 除草噻唑化合物

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