WO1993019054A1 - Nitro-anilines n-heterocycliques utilisees comme fongicides - Google Patents

Nitro-anilines n-heterocycliques utilisees comme fongicides Download PDF

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Publication number
WO1993019054A1
WO1993019054A1 PCT/US1993/002785 US9302785W WO9319054A1 WO 1993019054 A1 WO1993019054 A1 WO 1993019054A1 US 9302785 W US9302785 W US 9302785W WO 9319054 A1 WO9319054 A1 WO 9319054A1
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Prior art keywords
substituted
phenyl
alkyl
alkenyl
halo
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PCT/US1993/002785
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English (en)
Inventor
Christopher S. Galka
Brent J. Rieder
John K. Swayze
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Dowelanco
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Priority to JP5516833A priority Critical patent/JPH07500116A/ja
Priority to BR9305466A priority patent/BR9305466A/pt
Publication of WO1993019054A1 publication Critical patent/WO1993019054A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond

Definitions

  • This invention provides new anilino heterocyclic
  • the invention provides new anilino heterocyclic compounds that are useful as plant fungicides, new plant fungicide compositions utilizing the new compounds, and new methods of combating plant pathogens utilizing the new
  • the present invention provides a method of inhibiting plant pathogens which comprises applying an
  • R 1 and R 2 are independently H, NO 2 , halo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4
  • R 1 is not CN, or CONR 5 R 6 , where R 5 and R 6 are H, C 1 -C 4 alkyl, C 3 -C 7 alkenyl, C 3 - C 7 cycloalkyl or cycloalkenyl, or R 5 and R 6 together with the nitrogen atom to which they are attached form a 5-7 member ring containing up to three additional heteroatoms selected from O, N, and S; R 3 is H, halo, NR 5 R 6 , C 1 -C 6 haloalkyl, C 1 - C 6 alkoxy, C 1
  • R4 is H, COOR 7 , CONR 5 R 6 , CHO, COR 7 , or SO 2 R 7 , SO 2 NR 5 R 6 , where R 5 and R 6 are as defined above and R 7 is C 1 -C 8 alkyl, C 3 -C 8 alkenyl, C 2 -C 8 branched alkyl, C 1 -C 4 haloalkyl, aralkyl, phenyl, or substituted phenyl;
  • Het is a group selected from:
  • Q is S or O
  • R 10 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • alkynyl C 3 -C 8 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, NO 2 , C ⁇ , SC ⁇ , CO 2 H, CO ⁇ R 5 R 6 where R 5 and R 6 are as defined above, CO 2 R 7 where R 7 is as defined above, or
  • R 11 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • alkynyl C 3 -C 8 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, aralkyl, (C 3 -C 7 cycloalkyl)methyl, phenyl, substituted phenyl, pyridyl, substituted pyridyl, furyl, substituted furyl, thienyl, substituted thienyl, S(O) m R 7 , OR 7 , NHR 7 , NR 5 R 6 , NR 7 R 7 , NH 2 , , , , ; where m, Q, R 5 , R 6 , and R 7 are
  • R 12 is H, halo, CN, CO 2 H, halo C 1 -C 3 alkyl, phenyl, substituted phenyl, CONR 5 R 6 , or CO 2 R 7 where R 5 , R 6 , and R 7 are as defined above;
  • R 13 is H, halo, CN, CO 2 H, halo C 1 -C 3 alkyl, phenyl, substituted phenyl, CONR 5 R 6 , or CO 2 R 7 where R 5 , R 6 , and R 7 are as defined above;
  • R 14 is C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 branched alkyl or alkenyl, C 1 -C 8 haloalkyl, phenyl,
  • R 15 is H, halo, NO 2 , CN, CO 2 H, CONR 5 R 6 , or CO 2 R 7 where R 5 , R 6 , and R 7 are as defined above;
  • R 16 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • R 17 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • R 18 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 8 haloalkyl, CN, NO 2 , C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 haloalkylthio, phenyl, substituted phenyl, thienyl, substituted thienyl, furyl, substituted furyl, pyridyl, substituted pyridyl, aralkyl, phenoxy, or substituted phenoxy; R 18 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • alkynyl C 3 -C 6 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 8 haloalkyl, CN, NO 2 , C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 haloalkylthio, phenyl, substituted phenyl, thienyl, substituted thienyl, furyl, substituted furyl, pyridyl, substituted pyridyl, aralkyl, phenoxy, or substituted phenoxy, S(O) n R', where n is 0-3, and R' is H, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 - C6 branched alkyl or alkenyl, phenyl,
  • R 19 is C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 6 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, phenyl, substituted phenyl, or aralkyl;
  • R 20 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • alkynyl C 3 -C 6 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 6 haloalkyl, pyridyl, substituted pyridyl, furyl, substituted furyl, thienyl, substituted thienyl, phenyl, or substituted phenyl;
  • R 21 and R 21 ' are C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C3-C8 alkynyl, C 3 -C S branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 6 haloalkyl, pyridyl, substituted pyridyl, furyl, substituted furyl, thienyl, substituted thienyl, phenyl, or substituted phenyl, aralkyl, COR 7 , CR 7' R 7' COOR 7 , CR 7' R 7' CONR 5 R 6 , Or S(O) m R 7 / where m and R 7 are as defined above and R 7 ' is H or C 1 -C 3 alkyl;
  • R 22 is H, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 - C ⁇ branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or
  • R 23 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • alkynyl C 3 -C 8 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 8 haloalkyl, NO 2 , CN, SCN, CO 2 H, CONR 5 R 6 where R 5 and R 6 are as defined above, CO 2 R 7 , S(O) m R 7 where m and R 7 are as defined above, phenyl, substituted phenyl, pyridyl, substituted pyridyl, furyl, substituted furyl, thienyl, substituted thienyl, or aralkyl.
  • the invention also provides novel compounds of the formula (1):
  • R 1 and R 2 are independently H, NO 2 , halo, C 1 -C 6 alkyl,
  • alkylsulfonyl phenylsulfonyl, substituted phenylsulfonyl, SO 2 NR 5 R 6 , C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, COOR 5 , or CN, provided R 1 is not CN, or CONR 5 R 6 ;
  • R 3 is H, halo, NR 5 R 6 , C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, benzyloxy, substituted benzyloxy, benzylthio, or substituted benzylthio;
  • R 4 is H, COOR 7 , CONR 5 R 6 , CHO, COR 7 , SO 2 R 7 , or SO 2 NR 5 R 6 ;
  • R 5 and R 6 are H, C 1 -C 4 alkyl, C 3 -C 7 alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, or R 5 and R 6 together with the nitrogen atom to which they are attached form a 5-7 member ring containing up to three additional heteroatoms selected from O, N, and S;
  • R 7 is C 1 -C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 branched alkyl, C 1 -C 4 haloalkyl, aralkyl, phenyl, or substituted phenyl; Het is a group selected from:
  • R 12 is H, halo, CN, CO 2 H, halo C 1 -C 3 alkyl, phenyl, substituted phenyl, CONR 5 R 6 , or CO 2 R 7 where R 5 , R 6 , and R 7 are as defined above;
  • R 13 is H, halo, CN, CO 2 H, halo C 1 -C 3 alkyl, phenyl, substituted phenyl, CONR 5 R 6 , or CO 2 R 7 where R 5 , R 6 , and R 7 are as defined above;
  • R 14 is C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 branched alkyl or alkenyl, C 1 -C 8 haloalkyl, phenyl,
  • R 15 is H, halo, NO 2 , CN, CO 2 H, CONR 5 R 6 , or CO 2 R 7 where R 5 , R 6 , and R 7 are as defined above;
  • R 16 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • R 17 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 8 haloalkyl, CN, NO 2 , C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 haloalkylthio, phenyl, substituted phenyl, thienyl, substituted thienyl, furyl, substituted furyl, pyridyl, substituted pyridyl, aralkyl, phenoxy, or substituted phenoxy; R 17 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • alkynyl C 3 -C 6 branched alkyl or alkenyl, C 3 -C7 cycloalkyl or cycloalkenyl, C 1 -C 8 haloalkyl, CN, NO 2 , C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 haloalkylthio, phenyl, substituted phenyl, thienyl, substituted thienyl, furyl, substituted furyl, pyridyl, substituted pyridyl, aralkyl, phenoxy, or substituted phenoxy;
  • R 18 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • alkynyl C 3 -C 6 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 8 haloalkyl, CN, NO2, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 haloalkylthio, phenyl, substituted phenyl, thienyl, substituted thienyl,.
  • R 20 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • alkynyl C 3 -C 6 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 8 haloalkyl, pyridyl, substituted pyridyl, furyl, substituted furyl, thienyl, substituted thienyl, phenyl, or substituted phenyl;
  • R 21 and R 21' are C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 6 haloalkyl, pyridyl, substituted pyridyl, furyl, substituted furyl, thienyl, substituted thienyl, phenyl, substituted phenyl, aralkyl, COR 7 , CR 7' R 7' COOR 7 ,
  • R 22 is H, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 - C 8 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or
  • cycloalkenyl C 1 -C 6 haloalkyl, aralkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, (C 5 -C 7 cycloalkyl)methyl, halo/ CN, SCN, N02, phenyl, substituted phenyl, phenoxy, substituted phenoxy, pyridyl, substituted pyridyl, furyl, substituted furyl, thienyl, substituted thienyl, or NR 5 R 6 where R 5 and R 6 are as defined above; and
  • R 23 is H, halo, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8
  • alkynyl C 3 -C 8 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, C 1 -C 8 haloalkyl, NO 2 , CN, SCN, CO 2 H, CONR 5 R 6 , CO 2 R 7 , COR 7 , S(O) m R 7 , phenyl, substituted phenyl, pyridyl, substituted pyridyl, furyl, substituted furyl, thienyl, substituted thienyl, or aralkyl, where m, R 5 , R 6 , and R 7 are as defined above; provided that the following compounds are excluded: a) 2-methyl-5-(2,4-dinitrophenylamino)-1,3,4-oxadiazole; b) N-methyl-5-trifluoromethyl-2-(2-chloro-4,6-dinitroanilino)-1,3,4-thiadia
  • Another aspect of the invention comprises compounds having the following general formula (10):
  • Q is S or O
  • R 1 and R 2 are independently H, NO 2 , halo, C 1 -C 8 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4
  • R 3 is H, halo, NR 5 R 6 , C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 alkylthio, C 1 -C 6 haloalkylthio, phenoxy, substituted phenoxy, phenylthio, substituted phenylthio, benzyloxy, substituted benzyloxy, benzylthio, or substituted benzylthio;
  • R 5 and R 6 are H, C 1 -C 4 alkyl, C 3 -C 7 alkenyl, C 3 -C 7
  • cycloalkyl or cycloalkenyl or R 5 and R 6 together with the. nitrogen atom to which they are attached form a 5-7 member ring containing up to three additional heteroatoms selected from O, N, and S;
  • R 11 ' is C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 branched alkyl or alkenyl, C 3 -C 7 cycloalkyl or cycloalkenyl, aralkyl, (C 3 -C 7 cycloalkyl)methyl, halo C 1 -C 8 alkyl, phenyl, substituted phenyl, pyridyl, substituted pyridyl, furyl, substituted furyl, thienyl, substituted thienyl; and
  • R 24 and R 24' are independently Cl or Br.
  • the invention also provides a method of inhibiting plant pathogens which comprises applying an effective amount of a compound of formula (10) to the locus of the pathogen.
  • the invention also provides a method of inhibiting a nematode population which comprises applying to the locus of a nematode, a nematode inactivating amount of a compound of the formula (1) or (10) as defined above.
  • the invention also provides a method of inhibiting an insect or mite population which comprises applying to the locus of the insect or arachnid an effective insect or mite inactivating amount of a compound of formula (1) or (10).
  • halo refers to a F, Cl, Br, or I atom.
  • haloalkyl refers to straight chain, branched chain, and cyclo groups.
  • HPLC refers to a high pressure liquid
  • substituted phenyl refers to phenyl
  • C 1 -C 6 alkyl substituted with C 1 -C 6 alkyl, C 2 -C 7 alkenyl, C 2 -C 7 alkynyl, C 3 -C 7 branched alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo, hydroxy, NO 2 , C 1 -C 6 haloalkyl, C 1 -C 6
  • substituted phenoxy substituted phenoxy
  • aralkyl refers to such groups wherein the aryl portion is phenyl or substituted phenyl and the alkyl portion is C 1 -C 3 straight chain or C 2 -C 3 branched chain, e. g. , , or .
  • Substituted pyridyl, substituted furyl, and substituted thienyl refer to such groups substituted with halo, halo C 1 -C 4 alkyl, CN, NO 2 , C 1 -C 4 alkyl, C 3 -C 4 branched alkyl, phenyl, (C 1 -C 4 ) alkoxy, or halo (C 1 -C 4 ) alkoxy.
  • the invention includes salts of the compounds of formulas 1, 10 and 10A. Specifically contemplated are compounds of those formulas wherein R 4 is
  • n 1 or 2;
  • o-DTI refers to the group
  • Y and Z are NH 2 and the other is halo.
  • the reaction is preferrably carried out in the presence of a base such as an alkali metal hydroxide, carbonate, hydride or alkaline earth metal hydroxide or carbonate.
  • bases are sodium hydride, sodium hydroxide, sodium carbonate, potassium carbonate, potassium t-butoxide, sodium bicarbonate and potassium hydroxide.
  • the reaction is carried out in a nonreactive organic solvent such as tetrahydrofuran, at a temperature in the range from -20 to 200°C. It is preferred for Y to be halo and Z to be NH 2 .
  • Halogenation is typically carried out by reacting the compound of formula (1) with a small excess of elemental bromine, chlorine, or iodine in CH 2 CI 2 or CHCI 3 . Bromination andchlorination usually proceed rapidly at room temperature.
  • Iodination may require addition of potassium carbonate or sodium carbonate and brief heating to reflux.
  • Other halogenating agents such as N-bromosuccudimide and N-chlorosuccinimide may also be used.
  • Nitration is typically carried out by dissolving the compound of formula (1) in concentrated sulfuric acid and adding excess fuming nitric acid at room temperture. If no conversion has occurred within ten minutes, brief heating at 100°C may be used.
  • R 10' is H or halo.
  • the starting materials used in preparing compounds of the invention are commercially available or they are readily prepared by known synthetic methods.
  • the following table identifies some of the available sources for the starting materials.
  • 5-aminoisothiazole starting materials can be prepared by the routes illustrated in the following Schemes 1A-1C:
  • 5-Aminoisoxazole starting materials can be prepared, for example, by the procedure illustrated in Scheme 2.
  • 2-Aminothiazole starting materials can be prepared, for example, by the procedure illustrated in Scheme 3.
  • 2-Amino-1,3,4-oxadiazole starting materials can be prepared, for example, by the procedure illustrated in Scheme 4.
  • 2-Amino-1,3,4-thiadiazole starting materials can be prepared, for example, by the pro.cedure illustrated in Schemes 5A and 5B
  • 5-Aminopyrazole starting materials can be prepared, for example, by the procedures illustrated in Scheme 6A-6D.
  • 5-Amino-1, 2 , 4-thiadiazole starting materials can be prepared, for example, by the procedures illustrated in
  • the mixture was first diluted with ice water, then flooded with 150 mL of water.
  • the resulting yellow powder was
  • the compounds of the present invention have been found to control fungi, particularly plant pathogens. When employed in the treatment of plant fungal diseases, the compounds are applied to the plants in a disease inhibiting and phytologically acceptable amount.
  • inhibiting and phytologically acceptable amount refers to an amount of a compound of the invention which kills or inhibits the plant disease for which control is desired, but is not significantly toxic to the plant. This amount will generally be from about 1 to 1000 ppm, with 10 to 500 ppm being preferred. The exact concentration of compound required varies with the fungal disease to be controlled, the type formulation employed, the method of application, the particular plant species, climate conditions and the like. A suitable application rate is typically in the range from .25 to 4 lb/A.
  • the compounds of the invention may also be used to protect stored grain and other non-plant loci from fungal infestation.
  • test compounds were formulated for application by dissolving 50 mg of the compound into 1.25 ml of solvent .
  • the solvent was prepared by mixing 50 ml of "Tween 20"
  • test compounds were applied by foliar spray.
  • the following plant pathogens and their corresponding plants were employed. Pathogen Designation in Host
  • the formulated technical compounds were sprayed on all foliar surfaces of the host plant (or cut' berry) to past run-off. Single pots of each host plant were placed on raised, revolving pedestals in a fume hood. Test solutions were sprayed on all foliar surfaces. All treatments were allowed to dry and the plants were inoculated with the appropriate pathogens within 2-4 hours.
  • Tables 1-9 report the activity of typical compounds of the present invention when evaluated in this experiment. The effectiveness of test compounds in controlling disease wasrated using the following scale.
  • the compounds of formulas (1) and (10) are useful for reducing populations of insects and mites, and are used in a method of inhibiting an insect or mite population which comprises applying to a locus of the insect or mite an effective insect- or mite-inactivating amount of a compound of formulas (1) and (10).
  • locus of insects or mites is a term used herein to refer to the environment in which the insects or mites live or where their eggs are present, including the air surrounding them, the food they eat, or objects which they contact.
  • plant-ingesting insects or mites can be controlled by applying the active compound to plant parts, which the insects or mites eat, particularly the foliage. It is contemplated that the
  • inhibitors might also be useful to protect textiles, paper, stored grain, or seeds by applying an active compound to such substance.
  • inhibiting an insect or mite refers to a decrease in the numbers of living insects or mites; or a decrease in the number of viable insect or mite eggs. The extent of reduction accomplished by a compound depends, of course, upon the application rate of the compound, the
  • insect-inactivating or mite-inactivating amount should be used.
  • the present invention is directed to a method for inhibiting a mite which comprises applying to a plant an effective mite-inactivating amount of a compound of formulas (1) and (10) in accordance with the present invention.
  • each test compound was formulated as a 400 ppm solution, and this solution was then diluted with water to give the indicated concentrations.
  • the 400 ppm solution was prepared by combining 19.2 mL of .05% solution of Tween 20 (polyoxyethylene (20) sorbitan monolaurate) in water with a solution of 8 mg of the compound in .8 mL of acetone/EtOH (9/1).
  • Twospotted spider mites ⁇ Tetranychus urticae Koch) and melon aphids (Aphis gossypii Glover) are introduced on squash cotyledons and allowed to establish on both leaf surfaces. Other plants in the same treatment pot are left uninfested. The leaves are then sprayed with test solution using an atomizing sprayer at 17 psi. Both surfaces of the leaves are covered until runoff, and then allowed to dry. Activity of a compound is determined 48 hours after treatment. Activity is rated as a percent based on the mites/aphids present in plants sprayed with solvent alone.
  • undecimpuctata howardi Barber is evaluated by adding one mL of test solution containing a predetermined concentration of test compound to a cup containing a kernel of corn in 16 g of sterile soil. This produces a soil concentration of 24 ppm. After 1.5 to 2 hours of drying, five 4th instar corn rootworm larvae are added to the individual cups. Mortality is measured at 3-4 days by emptying the cup onto a pan and inspecting the soil for live rootworms.
  • CRW refers to corn rootworm
  • SAW Southern armyworm
  • SM refers to twospotted spider mites
  • MA refers to melon aphids.
  • Compound CRW CRW SAW SAW SM MA refers to melon aphids.
  • Another aspect of the invention is a method of inhibiting a nematode population which comprises applying to a locus of a nematode an effective nematode inactivating amount of a compound of formula (1)or (10).
  • inhibiting a nematode refers to a decrease in the numbers of living nematodes. The extent of reduction accomplished by a compound depends upon the application rate of the compound, the
  • nematode-inactivating amount should be used.
  • nematode-inactivating amount is used to describe the amount, which is sufficient to cause a measurable reduction in the treated nematode population.
  • nematicides are typically applied as aqueous drenches around growing plants or applied incrementally via irrigation
  • nematicides When applied as granules, nematicides may be
  • compositions which are important embodiments of the invention, and which comprise a compound of formula (1) or (10) and a phytologically-acceptable inert carrier.
  • the compositions are either concentrated formulations which are dispersed in water for application, or are dust or granular formulations- which are applied without further treatment.
  • the compositions are prepared according to procedures and formulae which are conventional in the agricultural chemical art, but which are novel and important because of the presence therein of the compounds of this invention. Some description of the formulation of the compositions will be given, however, to assure that agricultural chemists can readily prepare any desired composition.
  • the dispersions in which the compounds are applied are most often aqueous suspensions or emulsions prepared from concentrated formulations of the compounds.
  • water-soluble, water-suspendable or emulsifiable formulations are either solids usually known as wettable powders, or liquids usually known as emulsifiable concentrates or aqueous suspensions.
  • Wettable powders which may be compacted to form water dispersible granules, comprise an intimate mixture of the active compound, an inert carrier and surfactants.
  • concentration of the active compound is usually from about 10%to about 90% by weight.
  • the inert carrier is usually chosen from among the attapulgite clays, the montmorillonite clays, the diatomaceous earths, or the purified silicates.
  • Effective surfactants comprising from about 0.5% to about 10% of the wettable powder, are found among the sulfonated lignins, the condensed naphthalenesulfonates, the naphthalenesulfonates, the alkylbenzenesulfonates, the alkyl sulfates, and non-ionic surfactants such as ethylene oxide adducts of alkyl phenols.
  • Emulsifiable concentrates of the compounds comprise a convenient concentration of a compound, such as from about 50 to about 500 grams per liter of liquid, equivalent to about 10% to about 50%, dissolved in an inert carrier which is either a water miscible solvent or a mixture of
  • Useful organic solvents include aromatics, especially the xylenes, and the petroleum fractions, especially the high-boiling naphthalenic and olefinic portions of petroleum such as heavy aromatic naphtha.
  • Other organic solvents may also be used, such as the terpenic solvents including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol.
  • Suitable emulsifiers for emulsifiable concentrates are chosen from conventional nonionic surfactants, such as those discussed above.
  • Aqueous suspensions comprise suspensions of
  • water-insoluble compounds of this invention dispersed in an aqueous vehicle at a concentration in the range from about.5% to about 50% by weight.
  • Suspensions are prepared by finely grinding the compound, and vigorously mixing it into a vehicle comprised of water and surfactants chosen from the same types discussed above.
  • Inert ingredients such as inorganic salts and synthetic or natural gums, may also be added, to increase the density and viscosity of the aqueous vehicle. It is often most effective to grind and mix the compound at the same time by preparing the aqueous mixture, and homogenizing it in an implement such as a sand mill, ball mill, or piston-type homogenizer.
  • the compounds may also be applied as granular
  • compositions which are particularly useful for applications to the soil.
  • Granular compositions usually contain from about 0.5% to about 10% by weight of the compound, dispersed in an inert carrier which consists entirely or in large part of clay or a similar inexpensive substance.
  • Such compositions are usually prepared by dissolving the compound in a suitable solvent, and applying it to a granular carrier which has been pre-formed to the appropriate particle size, in the range of from about 0.5 to 3 mm.
  • Such compositions may also be
  • Dusts containing the compounds are prepared simply by intimately mixing the compound in powdered form with a suitable dusty agricultural carrier, such as kaolin clay, ground volcanic rock and the 'like. Dusts can suitably contain from about 1% to about 10% of the compound. It is equally practical, when desirable for any reason, to apply the compound in the form of a solution in an
  • organic solvent usually a bland petroleum oil, such as the spray oils, which are widely used in agricultural chemistry.
  • Insecticides and miticides are generally applied in the form of a dispersion of the active ingredient in a liquid carrier. It is conventional to refer to application rates in terms of the concentration of active ingredient in the
  • carrier The most widely used, carrier is water.
  • the compounds of formula (1) and (10) can also be applied in the form of an aerosol composition.
  • the active compound is dissolved or dispersed in an inert carrier, which is a pressure-generating propellant mixture.
  • the aerosol composition is packaged in a container from which the mixture is dispensed through an atomizing valve.
  • Propellant mixtures comprise either low-boiling halocarbons, which may be mixed with organic solvents, or aqueous suspensions pressurized with inert gases or gaseous hydrocarbons.
  • the actual amount of compound to be applied to loci of insects and mites is not critical and can readily be
  • concentrations of from 10 ppm to 5000 ppm of compound are expected to provide good control. With many of the compounds, concentrations of from 100 to 1500 ppm will suffice.
  • a suitable application rate for the compounds is about 0.5 to 1.5 lb/A, typically applied in 50 gal/A of spray formulation containing 1200 to 3600 ppm of compound.
  • a suitable application rate is from about 100 to 1500 gal/A spray formulation, which is a rate of 100 to 1000 ppm.
  • the locus to which a compound is applied can be any locus inhabited by an insect or arachnid, for example, vegetable crops, fruit and nut trees, grape vines, and ornamental plants.
  • an insect or arachnid for example, vegetable crops, fruit and nut trees, grape vines, and ornamental plants.
  • mite species are specific to a particular host, the foregoing list of mite species provides exemplification of the wide range of settings in which the present compounds can be used.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention se rapporte à des composés hétérocycliques anilino, tels que 4-bromo-3-(4-fluorophényl)-N-(2,4-dinitro-6-(trifluorométhyl)-phényl)isothiazol-5-amine et N-(4-bromo-4-chloro-3-méthyle-5(4H)-isothiazolylidène)2,4-dinitro-6-(trifluorométhyl)benzénamine, qui possèdent un pouvoir fongicide ainsi qu'un pouvoir insecticide et nématicide.
PCT/US1993/002785 1992-03-26 1993-03-25 Nitro-anilines n-heterocycliques utilisees comme fongicides WO1993019054A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP5516833A JPH07500116A (ja) 1992-03-26 1993-03-25 殺菌剤としてのｎ−複素環式ニトロアニリン
BR9305466A BR9305466A (pt) 1992-03-26 1993-03-25 Nitroanilinas n-heterocíclicas usadas como fungicidas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US85827192A 1992-03-26 1992-03-26
US07/858,271 1992-03-26

Publications (1)

Publication Number Publication Date
WO1993019054A1 true WO1993019054A1 (fr) 1993-09-30

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JP (1) JPH07500116A (fr)
AU (1) AU3934693A (fr)
BR (1) BR9305466A (fr)
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WO (1) WO1993019054A1 (fr)

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WO1994021617A1 (fr) * 1993-03-19 1994-09-29 Dowelanco Procede de preparation d'isothiazoles halogenes
EP0627423A1 (fr) * 1992-01-22 1994-12-07 Nissan Chemical Industries, Limited Derive de pyrazole substitue et bactericide agrohorticole
WO1995022530A1 (fr) * 1994-02-18 1995-08-24 Bayer Aktiengesellschaft N-pyrazolylanilines et n-pyrazolylaminopyridines utilisees comme parasiticides
WO1997008149A1 (fr) * 1995-08-31 1997-03-06 Bayer Aktiengesellschaft 5-aminopyrazoles substitues et leur utilisation pour combattre des animaux nuisibles
EP0846686A1 (fr) * 1996-11-30 1998-06-10 Pfizer Limited Dérivés de phenyl-1-pyrazoles et leur utilisation comme parasiticide
US6069157A (en) * 1997-11-25 2000-05-30 Pfizer Inc. Parasiticidal compounds
US6403622B1 (en) 1998-10-06 2002-06-11 Bayer Aktiengesellschaft Phenylacetic acid heterocyclyl amides having an insecticidal effect
US6409988B1 (en) 1999-07-01 2002-06-25 3-Dimensional Pharmaceuticals, Inc. Radiolabeled 1-aryl pyrazoles, the synthesis thereof and the use thereof as pest GABA receptor ligands
US6506784B1 (en) 1999-07-01 2003-01-14 3-Dimensional Pharmaceuticals, Inc. Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides
US6518266B1 (en) 1999-07-22 2003-02-11 3-Dimensional Pharmaceuticals 1- Aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides
US6545033B1 (en) 1999-10-06 2003-04-08 3-Dimensional Pharmaceuticals, Inc. Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides
US6586453B2 (en) 2000-04-03 2003-07-01 3-Dimensional Pharmaceuticals, Inc. Substituted thiazoles and the use thereof as inhibitors of plasminogen activator inhibitor-1
WO2006108224A1 (fr) * 2005-04-11 2006-10-19 Murdoch University Composés antiparasitaires
US7265144B2 (en) 2002-11-27 2007-09-04 Bayer Pharmaceuticals Corporation Anilinopyrazole derivatives useful for the treatment of diabetes
US7354944B2 (en) 2004-10-18 2008-04-08 Amgen Inc. Thiadiazole compounds and methods of use
US7381736B2 (en) 2004-09-02 2008-06-03 Metabasis Therapeutics, Inc. Thiazole and thiadiazole inhibitors of tyrosine phosphatases
DE102008039083A1 (de) 2008-08-21 2010-02-25 Bayer Schering Pharma Aktiengesellschaft Substituierte 5-Aminopyrazole und ihre Verwendung
DE102008039082A1 (de) 2008-08-21 2010-02-25 Bayer Schering Pharma Aktiengesellschaft Azabicyclisch-substituierte 5-Aminopyrazole und ihre Verwendung
US7737149B2 (en) 2006-12-21 2010-06-15 Astrazeneca Ab N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(3,5-dimethylpiperazin-1-yl)benzamide and salts thereof
EP2275422A1 (fr) 2006-12-20 2011-01-19 Bayer CropScience AG Pyrimidinylpyrazoles an tant qu'agents insecticides et parasiticides
US7897619B2 (en) 2007-07-17 2011-03-01 Amgen Inc. Heterocyclic modulators of PKB
US7919504B2 (en) 2007-07-17 2011-04-05 Amgen Inc. Thiadiazole modulators of PKB
CN103288771A (zh) * 2012-02-29 2013-09-11 中国中化股份有限公司 异噻唑类化合物及其作为杀菌剂的用途
WO2014007228A1 (fr) * 2012-07-03 2014-01-09 小野薬品工業株式会社 Composé ayant une activité agoniste sur un récepteur de la somatostatine, et leur utilisation à des fins médicales
US8686007B2 (en) 2011-04-22 2014-04-01 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use
US9062005B2 (en) 2009-03-03 2015-06-23 E I Du Pont De Nemours And Company Fungicidal pyrazoles
WO2016102435A3 (fr) * 2014-12-22 2016-09-09 Bayer Cropscience Aktiengesellschaft Nouveaux isothiazolamides, procédés pour leur préparation et leur utilisation comme fongicides
US9604965B2 (en) 2010-04-23 2017-03-28 Cytokinetics, Inc. Substituted pyridazines as skeletal muscle modulators
US9730886B2 (en) 2010-04-23 2017-08-15 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US9994528B2 (en) 2010-04-23 2018-06-12 Cytokinetics, Inc. Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
US10015966B2 (en) 2012-02-01 2018-07-10 E I Du Pont De Nemours And Company Fungicidal pyrazole mixtures
US10420764B2 (en) 2012-12-21 2019-09-24 Astrazeneca Ab Pharmaceutical formulation of N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-YL]-4-[(3R,5S)-3 ,5-dimethylpiperazin-1-YL] benzamide
WO2020051402A1 (fr) * 2018-09-06 2020-03-12 Fmc Corporation Pyrazoles fongicides substitués par nitroanilino
WO2021183721A1 (fr) * 2020-03-11 2021-09-16 Fmc Corporation Mélanges fongicides contenant des dérivés de pyrazole

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JP2855601B2 (ja) * 1992-08-04 1999-02-10 宇部興産株式会社 Ｎ−チアゾリルアニリン誘導体、その製法及び農園芸用の殺虫剤
TWI504350B (zh) * 2010-09-01 2015-10-21 Du Pont 殺真菌吡唑及其混合物
TW201321367A (zh) * 2011-10-25 2013-06-01 Du Pont 經１，３－二芳基取代之雜環殺蟲劑
AU2013277368A1 (en) * 2012-06-22 2015-01-15 E. I. Du Pont De Nemours And Company Fungicidal 4-methylanilino pyrazoles

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EP0627423A1 (fr) * 1992-01-22 1994-12-07 Nissan Chemical Industries, Limited Derive de pyrazole substitue et bactericide agrohorticole
EP0627423A4 (fr) * 1992-01-22 1995-02-15 Nissan Chemical Ind Ltd Derive de pyrazole substitue et bactericide agrohorticole.
WO1994021617A1 (fr) * 1993-03-19 1994-09-29 Dowelanco Procede de preparation d'isothiazoles halogenes
WO1995022530A1 (fr) * 1994-02-18 1995-08-24 Bayer Aktiengesellschaft N-pyrazolylanilines et n-pyrazolylaminopyridines utilisees comme parasiticides
WO1997008149A1 (fr) * 1995-08-31 1997-03-06 Bayer Aktiengesellschaft 5-aminopyrazoles substitues et leur utilisation pour combattre des animaux nuisibles
EP0846686A1 (fr) * 1996-11-30 1998-06-10 Pfizer Limited Dérivés de phenyl-1-pyrazoles et leur utilisation comme parasiticide
US6156782A (en) * 1996-11-30 2000-12-05 Pfizer Inc Parasiticidal compounds
US6069157A (en) * 1997-11-25 2000-05-30 Pfizer Inc. Parasiticidal compounds
US6403622B1 (en) 1998-10-06 2002-06-11 Bayer Aktiengesellschaft Phenylacetic acid heterocyclyl amides having an insecticidal effect
US6409988B1 (en) 1999-07-01 2002-06-25 3-Dimensional Pharmaceuticals, Inc. Radiolabeled 1-aryl pyrazoles, the synthesis thereof and the use thereof as pest GABA receptor ligands
US6506784B1 (en) 1999-07-01 2003-01-14 3-Dimensional Pharmaceuticals, Inc. Use of 1,3-substituted pyrazol-5-yl sulfonates as pesticides
US6518266B1 (en) 1999-07-22 2003-02-11 3-Dimensional Pharmaceuticals 1- Aryl-3-thioalkyl pyrazoles, the synthesis thereof and the use thereof as insecticides
US6545033B1 (en) 1999-10-06 2003-04-08 3-Dimensional Pharmaceuticals, Inc. Fused 1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoles, the synthesis thereof and the use thereof as pesticides
US6586453B2 (en) 2000-04-03 2003-07-01 3-Dimensional Pharmaceuticals, Inc. Substituted thiazoles and the use thereof as inhibitors of plasminogen activator inhibitor-1
US7265144B2 (en) 2002-11-27 2007-09-04 Bayer Pharmaceuticals Corporation Anilinopyrazole derivatives useful for the treatment of diabetes
US7381736B2 (en) 2004-09-02 2008-06-03 Metabasis Therapeutics, Inc. Thiazole and thiadiazole inhibitors of tyrosine phosphatases
US7354944B2 (en) 2004-10-18 2008-04-08 Amgen Inc. Thiadiazole compounds and methods of use
US7919514B2 (en) 2004-10-18 2011-04-05 Amgen Inc. Thiadiazole compounds and methods of use
US7700636B2 (en) 2004-10-18 2010-04-20 Amgen Inc. Thiadiazole compounds and methods of use
WO2006108224A1 (fr) * 2005-04-11 2006-10-19 Murdoch University Composés antiparasitaires
EP2275422A1 (fr) 2006-12-20 2011-01-19 Bayer CropScience AG Pyrimidinylpyrazoles an tant qu'agents insecticides et parasiticides
US10301267B2 (en) 2006-12-21 2019-05-28 Astrazeneca Ab Compounds
US9688640B2 (en) 2006-12-21 2017-06-27 Astrazeneca Ab Methods of treating cancer with a pyrazole derivative
US7737149B2 (en) 2006-12-21 2010-06-15 Astrazeneca Ab N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(3,5-dimethylpiperazin-1-yl)benzamide and salts thereof
US8604022B2 (en) 2006-12-21 2013-12-10 Astrazeneca Ab N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-1h-pyrazol-3-yl]-4-(3,4-dimethylpiperazin-1-yl)benzamide and salts thereof
US8129391B2 (en) 2006-12-21 2012-03-06 Astrazeneca Ab N-[5-[2-(3,5-Dimethoxyphenyl)ethyl]-1H-pyrazol-3-yl]-4-(3,4-dimethylpiperazin-1-yl)benzamide and salts thereof
US7919504B2 (en) 2007-07-17 2011-04-05 Amgen Inc. Thiadiazole modulators of PKB
US7897619B2 (en) 2007-07-17 2011-03-01 Amgen Inc. Heterocyclic modulators of PKB
DE102008039082A1 (de) 2008-08-21 2010-02-25 Bayer Schering Pharma Aktiengesellschaft Azabicyclisch-substituierte 5-Aminopyrazole und ihre Verwendung
DE102008039083A1 (de) 2008-08-21 2010-02-25 Bayer Schering Pharma Aktiengesellschaft Substituierte 5-Aminopyrazole und ihre Verwendung
US10448639B2 (en) 2009-03-03 2019-10-22 Fmc Corporation Fungicidal pyrazoles
EP2966063A1 (fr) * 2009-03-03 2016-01-13 E. I. du Pont de Nemours and Company Pyrazoles fongicides
US9655361B2 (en) 2009-03-03 2017-05-23 E I Du Pont De Nemours And Company Fungicidal pyrazoles
US9062005B2 (en) 2009-03-03 2015-06-23 E I Du Pont De Nemours And Company Fungicidal pyrazoles
EP2403834B1 (fr) * 2009-03-03 2015-12-02 E. I. du Pont de Nemours and Company Pyrazoles fongicides
US9730886B2 (en) 2010-04-23 2017-08-15 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US9994528B2 (en) 2010-04-23 2018-06-12 Cytokinetics, Inc. Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use
US11369565B2 (en) 2010-04-23 2022-06-28 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US9604965B2 (en) 2010-04-23 2017-03-28 Cytokinetics, Inc. Substituted pyridazines as skeletal muscle modulators
US10765624B2 (en) 2010-04-23 2020-09-08 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US10272030B2 (en) 2010-04-23 2019-04-30 Cytokinetics, Inc. Amino-pyrimidine skeletal muscle modulators
US10076519B2 (en) 2010-04-23 2018-09-18 Cytokinetics, Inc. Substituted pyridazines as skeletal muscle modulators
US8759380B2 (en) 2011-04-22 2014-06-24 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use
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US9278962B2 (en) 2011-04-22 2016-03-08 Cytokinetics, Inc. Certain heterocycles, compositions thereof, and methods for their use
US10015966B2 (en) 2012-02-01 2018-07-10 E I Du Pont De Nemours And Company Fungicidal pyrazole mixtures
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US10214540B2 (en) 2012-07-03 2019-02-26 Ono Pharmaceutical Co., Ltd. Compound having agonistic activity on somatostatin receptor, and use thereof for medical purposes
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US9975904B2 (en) 2012-07-03 2018-05-22 Ono Pharmaceutical Co., Ltd. Compound having agonistic activity on somatostatin receptor, and use thereof for medical purposes
US9630976B2 (en) 2012-07-03 2017-04-25 Ono Pharmaceutical Co., Ltd. Compound having agonistic activity on somatostatin receptor, and use thereof for medical purposes
US10420764B2 (en) 2012-12-21 2019-09-24 Astrazeneca Ab Pharmaceutical formulation of N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-YL]-4-[(3R,5S)-3 ,5-dimethylpiperazin-1-YL] benzamide
WO2016102435A3 (fr) * 2014-12-22 2016-09-09 Bayer Cropscience Aktiengesellschaft Nouveaux isothiazolamides, procédés pour leur préparation et leur utilisation comme fongicides
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CN112969688A (zh) * 2018-09-06 2021-06-15 Fmc公司 杀真菌的硝基苯胺取代的吡唑类化合物
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CN112969688B (zh) * 2018-09-06 2024-06-04 Fmc公司 杀真菌的硝基苯胺取代的吡唑类化合物
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Also Published As

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JPH07500116A (ja) 1995-01-05
HUT69739A (en) 1995-09-28
AU3934693A (en) 1993-10-21
EP0586686A1 (fr) 1994-03-16
BR9305466A (pt) 1994-12-20

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