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WO1998005652A2 - Amides cycliques arthropodicides et fongicides - Google Patents

Amides cycliques arthropodicides et fongicides Download PDF

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Publication number
WO1998005652A2
WO1998005652A2 PCT/US1997/012809 US9712809W WO9805652A2 WO 1998005652 A2 WO1998005652 A2 WO 1998005652A2 US 9712809 W US9712809 W US 9712809W WO 9805652 A2 WO9805652 A2 WO 9805652A2
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Prior art keywords
alkyl
optionally substituted
chr
phenyl
haloalkyl
Prior art date
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PCT/US1997/012809
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English (en)
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WO1998005652A3 (fr
Inventor
Richard James Brown
Dominic Ming-Tak Chan
David Alan Clark
Joseph Eugene Drumm, Iii
Gerard Michael Koether
Stephen Frederick Mccann
Morris Padgett Rorer
Thomas Paul Selby
Michael Paul Walker
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EIDP Inc
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EI Du Pont de Nemours and Co
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Publication date
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Priority to EP97936152A priority Critical patent/EP0934283A2/fr
Priority to AU38890/97A priority patent/AU3889097A/en
Priority to BR9711816-8A priority patent/BR9711816A/pt
Priority to JP10507942A priority patent/JP2000516583A/ja
Publication of WO1998005652A2 publication Critical patent/WO1998005652A2/fr
Publication of WO1998005652A3 publication Critical patent/WO1998005652A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D403/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D417/14—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 three or more hetero rings
    • 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
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • C 3 -Cg cycloalkyl C 2 -C 4 alkylcarbonyl; C 2 -C 4 alkoxycarbonyl; halogen; cyano; nitro; hydroxy; amino; NH(C ⁇ -C£ alkyl); N(C j -Cg alkyl)2; or mo ⁇ holinyl;
  • Z is selected from: i) C -C 8 cycloalkyl, C -Cg cycloalkenyl and phenyl, each substituted with
  • R 29 is H; C,-C 6 alkyl; C r C 6 haloalkyl; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; C 2 -C 6 alkynyl; C 2 -C 6 haloalkynyl; C -C $ cycloalkyl; or benzyl optionally substituted on the phenyl ring with 1 -2 groups independently selected from halogen, C C alkyl, Cj-C 4 haloalkyl, C C 4 alkoxy, Cj-C 4 haloalkoxy, nitro and cyano;
  • Alkylthioalkylthio denotes alkylthio substitution on alkylthio.
  • alkoxyalkylthio denotes alkoxy substitution on alkylthio and “alkylthioalkoxy” denotes alkylthio substitution on alkoxy.
  • Alkylsulfinyl includes both enantiomers of an alkylsulfinyl group.
  • nonaromatic heterocyclic ring system denotes fully saturated heterocycles as well as partially or fully unsaturated heterocycles where the H ⁇ ckel rule is not satisfied by any of the rings in the ring system.
  • 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.
  • the salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammoma, or "triemylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a phenol.
  • organic bases e.g., pyridine, ammoma, or "triemylamine
  • inorganic bases e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium
  • E is selected from the group 1,2-phenylene; 1,5-, 1,6-, 1,7-, 1,8-, 2,6-, 2,7-, 1 ,2-, and 2,3-naphthalenediyl; 1 H-pyrrole- 1 ,2-, 2,3- and
  • Preferred 5 selected from the group: 4-[2-[[3-( 1 ,3-benzodioxol-5-yl)- 1 ,2,4-thiadiazol-5-yl]oxy]phenyl]-2,4-dihydro- 5-methoxy-2-methyl-3H- 1 ,2,4-triazol-3-one;
  • 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.
  • arthropodicidal compositions of the present invention which comprise the above preferred compounds.
  • R 9 is other than N(R 26 )(R 28 ) and pyridinyloxymethyl; and R 9 is other than C 2 -C 6 alkyl substituted with naphthalenyl, phenoxy, benzyloxy each aromatic ring optionally substituted with one of R 1 -, R 12 , or both R n and R 12 ; and R 9 is other than C 2 -C 6 alkoxy substituted with 1-2 phenyl, naphthalenyl, phenoxy, benzyloxy, pyridinyl, pyrimidinyl, thienyl or furanyl, each aromatic ring optionally substituted with one of R 1 * , R 12 , or both R 11 and R 12 .
  • alkylating agents which can convert carbonyl compounds of Formula 1 to compounds of Formula I are dialkyl sulfates such as dimethyl sulfate, haloalkyl sulfonates such as methyl trifluoromethanesulfonate, and alkyl halides such as iodomethane and propargyl bromide (Method 4). These alkylations can be conducted with or without additional base.
  • Esters of Formula 5a can be prepared from copper (I)-catalyzed reaction of malonate esters of Formula 7 with substituted aryl halides of Formula 8 according to methods adapted from A. Osuka, T. Kobayashi and H. Suzuki, Synthesis, (1983), 67 and M. S. Malamas, T. C. Hohman, and J. Millen, J. Med. Chem., 1994, 37, 2043-2058, and illustrated in Scheme 3. Procedures to prepare compounds of Formula 8 are described below (see Scheme 33).
  • esters of Formula 9 can also be prepared by forming the Y 2 bridge using conventional nucleophilic substitution chemistry (Scheme 7).
  • Displacement of an appropriate leaving group (Lg) in electrophiles of Formula 15 or 16 with a nucleophilic ester of Formula 14 affords compounds of Formula 9b.
  • a base for example sodium hydride, is used to generate the corresponding alkoxide or thioalkoxide of the compound of Formula 14.
  • N-Amino-ureas of Formula 23 can be prepared as illustrated in Scheme 17.
  • Treatment of an arylamine of Formula 25 with phosgene, thiophosgene, N,N'-carbonyldiimidazole, or NN-thiocarbonyldiimidazole produces the isocyanate or isothiocyanate of Formula 26.
  • a base can be added for reactions with phosgene or thiophosgene.
  • Isocyanates of Formula 26 can also be prepared by heating acylazides of Formula 25a in a solvent such as toluene or benzene (Curtius rearrangement).
  • Iodides of Formula 8 can be prepared from compounds of Formula 60 by the methods described above in Schemes 21-26 for various Y-Z combinations.
  • Compounds of Formula 60 can in turn be prepared from compounds of Formula 59 by functional group interconversions which are well known to one skilled in the art.
  • the compounds of Formula 59 can be prepared by treating compounds of Formula 58 with an organolithium reagent such as n-BuLi or LDA followed by trapping the intermediate with iodine (Beak, P., Snieckus, V. Ace. Chem. Res., (1982), 15, 306).
  • T 7 CO2H, CONR 2 , CONHR,
  • Compounds of Formula 78 can be prepared from compounds of Formula 77 by nucleophilic displacement with alkali metal alkoxides, alkali metal thioalkoxides (M + -T 14 ) (Scheme 37). Similar displacements on compounds of Formula 80 with compounds M + -T 15 provide compounds of Formula 81.
  • Compounds of Formula 79 can be prepared by reaction with amine derivatives in a suitable solvent.
  • the leaving groups Lg 1 in compounds of Formula 77 and 80 are any group known in the art to undergo a displacement reaction of this type. Examples of suitable leaving groups include chlorine, bromine, and sulfonyl and sulfonate groups. Examples of suitable inert solvents are dimethylformamide or dimethyl sulfoxide, dimethoxyethane, and methanol.
  • Lg Cl, Br, -SC--2V or OSC ⁇ V
  • V C r C 6 alkyl, C r C 6 haloalkyl, or 4-CH 3 -C,sH4
  • Compounds of Formula 84 can be prepared from compounds of Formula 82 by reaction with nucleophiles of Formula 83 in the presence of added base (Scheme 38). Similarly, reaction of compounds of Formula 54a with nucleophiles of Formula 85 leads to compounds of Formula 86.
  • Appropriate bases include alkali metal alkoxides such as potassium fert-butoxide, inorganic bases such as sodium hydride and potassium carbonate, or tertiary amines such as triethylamine, pyridine, l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and triethylenediamine.
  • Step A Preparation of ethyl l-(4-chlorophenvDcvclopropanecarboximidate hvdrochloride To a solution of l-(4-chlorophenyl)-l-cyclopropanecarbonitrile (10 g, 56.3 mmol) in ethyl ether (56 mL) is added absolute ethanol (3.4 mL). The solution is cooled to 0 °C and saturated with dry HC1 gas. The reaction mixture is then left to stand at ambient temperature for 11 days after which time it is filtered under a stream of dry nitrogen to give the title compound of Step A (11.60 g) as a white solid.
  • Methyl iodide (0.705 mL) is then added and the mixture is cooled in an ice bath and stirred for a further 0.5 h. The solution is concentrated and redissolved in methylene chloride. The solution is filtered through a pad of silica gel and concentrated to give the title compound of Step A (2.15 g) as a white solid.
  • Step A Preparation of 3-r(2-chlorophenyl methoxyl-5-(methylthioV 1.2.4- thiadiazole To a solution of 3-hydroxy-5-thiomethyl-l,2,4-thiadiazole (J. Het. Chem., ( 1979), 961 ) (0.8 g) in DMF (10 mL) was added potassium carbonate ( 1.12 g) and
  • Step B Preparation of l-f3-ftris(trifluoromemv0germyl1phenyl " [ethanone
  • Step D Preparation of 2,4-dihvdro-5-methoxy-2-methyl-4-f2-rrr ⁇ -[3- ftrisftrifluoromethv ⁇ germyllphenv ⁇ ethylidenelaminoloxylmethyljphenv ⁇ -3H-1.2.4-triazol-3-one
  • Step A Preparation of l-r3-rdimethyl(3,3,3- trifluoropropyDsilyllphenv ⁇ ethanone A 125 mL 4-neck flask was charged wi a suspension of magnesium pieces (1.09 g, 0.041 mole) in 8 mL of THF.
  • Step C Preparation of 4-r2-rrr ⁇ -r3-rdimethyl-(3.3.3- trifluoropropynsilvnphenyllethylidenelamino]oxy]methyllphenvn-2.4- dihvdro-5-methoxy-2-methyl-3H- 1 ,2.4-triazol-3-one
  • sodium hydride (0.84 g, 0.021 mole, 60% mineral oil dispersion) was suspended in 50 mL of dry THF.
  • the title compound of Step B (2.0 g, 6.9 mmol) was dissolved in dry THF (15 mL) and added dropwise causing gas evolution.
  • R J 3-(2-CN-Ph-C ⁇ C-).
  • 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.
  • 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.
  • 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. For further information regarding the art of formulation, see U.S. 3,235,361 ,
  • Example B Granule Compound 39 10.0% attapulgite granules (low volatile matter
  • 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.
  • 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.
  • 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.
  • 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 on mites, demonstrating ovicidal, larvicidal and chemosterilant activity against such families as Tetranychidae including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubriocuius.
  • TEST E The test suspension was sprayed to the point of run-off on grape seedlings. The following day the seedlings were inoculated with a spore suspension of Plasmopara viticola (the causal agent of grape downy mildew) and incubated in a saturated atmosphere at 20°C for 24 h, moved to a growth chamber at 20°C for 6 days, and then incubated in a saturated atmosphere at 20°C for 24 h, after which disease ratings were made.
  • Plasmopara viticola the causal agent of grape downy mildew
  • TEST F The test suspension was sprayed to the point of run-off on cucumber seedlings. The following day the seedlings were inoculated with a spore suspension of Botrytis cinerea (the causal agent of gray mold on many crops) and incubated in a saturated atmosphere at 20°C for 48 h, and moved to a growth chamber at 20°C for 5 days, after which disease ratings were made.
  • Botrytis cinerea the causal agent of gray mold on many crops
  • Results for Tests A-F are given in Table A.
  • a rating of 100 indicates 100% disease control and a rating of 0 indicates no disease control (relative to the controls).
  • a dash (-) indicates no test results.
  • ND indicates disease control not determined due to phytotoxicity.
  • Pieces of kidney bean leaves each approximately 6.5 cm 2 (1 square inch) in area, that had been infested on the undersides with 25 to 30 adult mites (Tetranychus urticae), were sprayed with their undersides facing up on a hydraulic sprayer with a solution of the test compound in 75:25 acetone-distilled water solvent. Spraying was accomplished by passing the leaves, on a conveyor belt, directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.138 kilograms of active ingredient per hectare (about 0.13 pounds per acre) at 207 kPa (30 p.s.i.).
  • the leaf squares were then placed underside-up on a square of wet cotton in a petri dish and the perimeter of the leaf square was tamped down onto the cotton with forceps so that the mites could not escape onto the untreated leaf surface.
  • the test units were held at 27°C and 50% relative humidity for 48 hours, after which time mortality readings were taken. Of the compounds tested, the following gave mortality levels of 80% or higher: 12, 13, 45, 54, 86, 88, 89, 90, 111, 113, 114, 115, 116, 117, 118, 119 and 126.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne des composés de formule (I) et leurs N-oxydes ainsi que des sels convenant à l'agriculture, utiles en tant que fongicides et arthropodicides. Dans ladite formule (I), A représente O, S, N, NR?5 ou CR14¿; G représente C ou N, à condition que lorsque G est C, A représente O, S ou NR5 et la liaison double flottante est rattachée à A; et lorsque G représente N, A représente N ou CR14 et la liaison double flottante est rattachée à A; W représente O, S, NH, N(alkyle C¿1-6?); ou NO(alkyle C1-6);X représente OR?1¿, S(O)¿mR?1 ou halogène; R1 représente alkyle C¿1-6?, haloalkyle C1-6, alcényle C2-6, haloalcényle C2-6, alcynyle C2-6, haloalcynyle C2-6, cycloalkyle C3-6, alkylcarbonyle C2-4 ou alcoxycarbonyle C2-4; R?2¿ représente H, alkyle C¿1-6?, haloalkyle C1-6, alcényle C2-6, haloalcényle C2-6, alcynyle C2-6, haloalcynyle C2-6, cycloalkyle C3-6, alkylcarbonyle C2-4, alcoxycarbonyle C2-4, hydroxy, alcoxy C1-2 ou acétyloxy; m vaut 0, 1 ou 2; et E, R?5¿, Y, Z et R14 sont comme définis dans la description. L'invention porte aussi sur des compositions contenant les composés de formule (I) et sur un procédé de lutte contre des maladies de plantes induites par des pathogènes fongiques des plantes, qui consiste à appliquer une dose efficace d'un composé de formule (I). Elle se rapporte encore à des compositions contenant les composés de formule (I) et à un procédé de lutte contre les arthropodes qui consiste à mettre les arthropodes ou leur environnement en contact avec une dose efficace d'un composé de formule (I).
PCT/US1997/012809 1996-08-01 1997-07-24 Amides cycliques arthropodicides et fongicides Ceased WO1998005652A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP97936152A EP0934283A2 (fr) 1996-08-01 1997-07-24 Amides cycliques arthropodicides et fongicides
AU38890/97A AU3889097A (en) 1996-08-01 1997-07-24 Arthropodicidal and fungicidal cyclic amides
BR9711816-8A BR9711816A (pt) 1996-08-01 1997-07-24 Composto, composição fungicida, método para controlar doenças de plantas causadas pelos agentes patogênicos f·ngicos de plantas, composição artropodicida e método para controlar artrópodes.
JP10507942A JP2000516583A (ja) 1996-08-01 1997-07-24 殺節足動物性および殺菌・殺カビ性の環状アミド類

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US2293396P 1996-08-01 1996-08-01
US60/022,933 1996-08-01

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WO1998005652A2 true WO1998005652A2 (fr) 1998-02-12
WO1998005652A3 WO1998005652A3 (fr) 1998-06-11

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JP (1) JP2000516583A (fr)
CN (1) CN1231663A (fr)
AU (1) AU3889097A (fr)
BR (1) BR9711816A (fr)
WO (1) WO1998005652A2 (fr)

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WO2000005222A1 (fr) * 1998-07-23 2000-02-03 Syngenta Participations Ag Pesticides derives de la dihydrotriazolone
WO2001019803A1 (fr) * 1999-09-15 2001-03-22 Basf Aktiengesellschaft Ether oximes insatures et leur utilisation dans la lutte contre la peste fongique et les parasites d'animaux
US6489487B1 (en) 1998-08-03 2002-12-03 Sumitomo Chemical Company, Limited Triazolone derivatives, use thereof, and intermediates therefor
US6824830B1 (en) * 1999-10-20 2004-11-30 Aventis Cropscience Gmbh Wood treatment
US7273879B2 (en) 2002-01-17 2007-09-25 Sumitomo Chemical Company, Limited Thiadiazole compounds and use thereof
EP2072506A1 (fr) * 2007-12-21 2009-06-24 Bayer CropScience AG Thiazolyloxyphenylamidine ou thiadiazolyloxyphenylamidine et son utilisation en tant que fongicide
CN102336744A (zh) * 2010-07-20 2012-02-01 中国中化股份有限公司 取代三唑啉酮醚类化合物及其作为杀菌、杀虫、杀螨剂的用途
US8686007B2 (en) 2011-04-22 2014-04-01 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use
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US9133175B2 (en) 2010-12-06 2015-09-15 Autifony Therapeutics Limited Compounds
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US9422252B2 (en) 2012-05-22 2016-08-23 Autifony Therapeutics Limited Triazoles as Kv3 inhibitors
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US9994528B2 (en) 2010-04-23 2018-06-12 Cytokinetics, Inc. Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
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US6489487B1 (en) 1998-08-03 2002-12-03 Sumitomo Chemical Company, Limited Triazolone derivatives, use thereof, and intermediates therefor
WO2001019803A1 (fr) * 1999-09-15 2001-03-22 Basf Aktiengesellschaft Ether oximes insatures et leur utilisation dans la lutte contre la peste fongique et les parasites d'animaux
US6824830B1 (en) * 1999-10-20 2004-11-30 Aventis Cropscience Gmbh Wood treatment
US7273879B2 (en) 2002-01-17 2007-09-25 Sumitomo Chemical Company, Limited Thiadiazole compounds and use thereof
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Also Published As

Publication number Publication date
CN1231663A (zh) 1999-10-13
AU3889097A (en) 1998-02-25
BR9711816A (pt) 1999-08-31
JP2000516583A (ja) 2000-12-12
WO1998005652A3 (fr) 1998-06-11
EP0934283A2 (fr) 1999-08-11

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