WO2007061966A2 - Composes amidinylphenyle et utilisation de ceux-ci en comme fongicides - Google Patents

Composes amidinylphenyle et utilisation de ceux-ci en comme fongicides Download PDF

Info

Publication number
WO2007061966A2
WO2007061966A2 PCT/US2006/044924 US2006044924W WO2007061966A2 WO 2007061966 A2 WO2007061966 A2 WO 2007061966A2 US 2006044924 W US2006044924 W US 2006044924W WO 2007061966 A2 WO2007061966 A2 WO 2007061966A2
Authority
WO
WIPO (PCT)
Prior art keywords
compound
alkyl
plant
caused
disease
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2006/044924
Other languages
English (en)
Other versions
WO2007061966A3 (fr
Inventor
Chi-Ping Tseng
Michael Caldwell Klapproth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of WO2007061966A2 publication Critical patent/WO2007061966A2/fr
Publication of WO2007061966A3 publication Critical patent/WO2007061966A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • 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

Definitions

  • This invention relates to certain amidinylphenyl compounds, their iV-oxides, agriculturally suitable salts and compositions, and methods of their use as fungicides.
  • One area of need is for compounds that are useful for controlling plant disease caused by Ascomycete fungal plant pathogens, such as powdery mildew disease of cereals and/or broadleaf crops.
  • Another area of need is for compounds that are useful for controlling plant disease caused by Basidiomycete fungal plant pathogens, such as rust disease of cereals and/or broadleaf crops.
  • World Patent Application- Publication WO 2003/093224 discloses certain phenylamidines of Formula i as new fungicidal active ingredients.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and A are broadly defined, m is 0, 1, 2 or 3.
  • This invention is directed to compounds of Formula 1 (including all geometric and stereoisomers), jV-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use as fungicides:
  • R 1 is C 1 -C 4 alkyl or C 3 -C 4 cycloalkyl
  • R 2 is C 1 -C 3 alkyl
  • R 3 is Br, Cl or I
  • R 4 is Cl; or C 1 -C 2 alkyl or C 1 -C 2 alkoxy, each optionally substituted with one to three substituents independently selected from halogen;
  • A is C or Si;
  • each R 5 is independently C 1 -C 2 alkyl optionally substituted with one to three substituents independently selected from halogen; and
  • R 5a is H or Cj-C 2 alkyl; provided that when A is Si, then R 5a is C 1 - C 2 alkyl.
  • This invention provides a method of controlling plant diseases caused by Ascomycete plant pathogens (e.g., powdery mildew diseases caused by Erysiphe spp., Uncinula necatur, Sphaerotheca fuligena and Podosphaera leucotrichd) and diseases caused by Helminthosporium, Pyrenophora teres and Rhyncosporiwn secalis.
  • This method comprises applying to the plant (e.g., a cereal or broadleaf crop) or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of a compound selected from the compounds of Formula 1, ⁇ T-oxides, and agriculturally suitable salts thereof.
  • This invention also provides a method of controlling plant diseases caused by Ascomycete plant pathogens (e.g., powdery mildew diseases caused by Erysiphe spp., Uncinula necatur, Sphaerotheca fuligena and Pod
  • Basidiomycete plant pathogens e.g., rust diseases caused by Puccinia spp., Hemileia vastatrix, Uromyces appendiculatus, Phakopsora pachyrhizi and Phakopsora meibomiae.
  • This method comprises applying to the plant (e.g., a cereal or broadleaf crop) or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of a compound selected from the compounds of Formula 1, .V-oxides, and agriculturally suitable salts thereof.
  • This invention also provides a method of controlling plant diseases caused by plant pathogens other than Ascomycete plant pathogens and Basidiomycete plant pathogens (e.g., Deuteromycetes plant pathogens).
  • This method comprises applying to the plant (e.g., a cereal or broadleaf crop) or portion thereof, or to the plant seed or seedling, a fungicidally effective amount of a compound selected from the compounds of Formula 1, JV-oxides, and agriculturally suitable salts thereof.
  • compositions comprising, “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
  • a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
  • “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
  • compositions of the present invention comprises a biologically effective amount of "a" compound of Formula 1 which should be read that the composition includes one or at least one compound of Formula 1.
  • seedling used either alone or in a combination of words means a young plant developing from the embryo of a seed.
  • the term “broadleaf used either alone or in words such as “broadleaf crop” means dicot or dicotyledon, a term used to describe a group of angiosperms characterized by embryos having two cotyledons.
  • alkyl includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, /-propyl, or the different butyl isomers.
  • Alkoxy includes, for example, methoxy and ethoxy.
  • Cycloalkyl includes, for example, cyclopropyl and cyclobutyl.
  • halogen includes fluorine, chlorine, bromine or iodine.
  • 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 4.
  • C 2 alkyl designates CH 3 CH 2 ;
  • C 3 alkyl designates, for example, CH 3 CH 2 CH 2 or (CH 3 ) 2 CH.
  • tertiary amines can form iV-oxides.
  • Synthetic methods for the preparation of iV-oxides of tertiary amines are very well known by one skilled in the art including the oxidation of tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as *-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as *-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethyldioxirane.
  • Compounds of this invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomers). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
  • salts of the compounds of Formula 1 are useful for control of fungal plant diseases (i.e. are agriculturally suitable).
  • the salts of the compounds of Formula 1 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.
  • the present invention comprises compounds selected from Formula 1, iV-oxides and agriculturally suitable salts thereof.
  • Embodiments of the present invention include: Embodiment Al.
  • Embodiment A2 A compound of Embodiment Al wherein R 1 is C 1 -C 2 alkyl.
  • Embodiment A3. A compound of Embodiment A2 wherein R 1 is ethyl.
  • Embodiment A4 A compound of Formula 1 wherein R 2 is C 1 -C 2 alkyl- Embodiment A5.
  • Embodiment A6 A compound of Formula 1 wherein R 3 is Br or Cl.
  • Embodiment A7 A compound of Embodiment A6 wherein R 3 is Br. .
  • Embodiment A8 A compound of Formula 1 wherein R 4 is Cl; or C]-C 2 alkyl or C 1 -
  • Embodiment A 12 A compound of Embodiment Al 1 wherein each R 5 is independently C 1 -C 2 alkyl optionally substituted with one to three Cl. Embodiment A13. A compound of Embodiment A12 wherein each R 5 is independently Cj alkyl optionally substituted with one to three Cl. Embodiment A 14. A compound of Formula 1 wherein A is C and R 5a is H. Embodiment Bl .
  • a method of controlling at least one plant fungal disease in cereal or broadleaf crops selected from the group consisting of powdery mildew disease caused by Erysiphe spp., Uncinula necatur, Sphaerothecafuligena and
  • Embodiment B2 A method of Embodiment Bl wherein at least one powdery mildew disease is controlled.
  • Embodiment B3. A method of Embodiment B2 wherein the plant disease is caused by
  • Embodiment B4 A method of Embodiment B2 wherein the plant disease is caused by
  • Embodiment B5. A method of Embodiment B2 wherein the plant disease is caused by Uncinula necatur.
  • Embodiment B6 A method of Embodiment B2 wherein the plant disease is caused by
  • Embodiment B7 A method of Embodiment Bl wherein at least one rust disease is controlled. .
  • Embodiment B8. A method of Embodiment B7 wherein the plant disease is caused by
  • Embodiment B9 A method of Embodiment B7 wherein the plant disease is caused by Puccinia striiformis.
  • Embodiment BlO A method of Embodiment B7 wherein the plant disease is caused by Puccinia graminis.
  • Embodiment BIl A method of Embodiment B7 wherein the plant disease is caused by Hemileia vastatrix.
  • Embodiment B 12. A method of Embodiment B7 wherein the plant disease is caused by Uromyces appendiculatus.
  • Embodiment B 13 A method of Embodiment B7 wherein the plant disease is caused by Phakopsora pachyrhizi.
  • Embodiment B 14 A method of any one of Embodiments Bl to Bl 3 wherein the plant is a dicot crop.
  • Embodiment B 15 A method of Embodiment Bl 4 wherein the dicot crop is selected from soybean, grape and cucurbit.
  • Embodiment B 16 A method of Embodiment Bl 5 wherein the dicot crop is soybean.
  • Embodiment B17 A method of Embodiment Bl 5 wherein the dicot crop is grape.
  • Embodiment B 18. A method of Embodiment Bl 5 wherein the dicot crop is cucurbit.
  • Embodiment Cl A compound of Formula 1 wherein R 1 is C 1 -C 3 alkyl or C 3 -C 4 cycloalkyl; R 2 is C 1 -C 2 alkyl; R3 is Br or Cl;
  • R 4 is Cl; or C 1 - C 2 alkyl or C 1 - C 2 alkoxy, each optionally substituted with one to three substituents independently selected from F and Cl; and each R 5 is independently C 1 -C 2 alkyl optionally substituted with one to three substituents independently selected from F and Cl.
  • Embodiment C2. A compound of Embodiment Cl wherein
  • R l is C 1 -C 2 alkyl; R 2 is methyl; R 3 is Br;
  • R 4 is Cl; or C 1 -C 2 alkyl or C 1 -C 2 alkoxy, each optionally substituted with one to three F; and each R 5 is independently C 1 -C 2 alkyl optionally substituted with one to three
  • R 1 is ethyl; R 2 is methyl; R 4 is C 1 alkyl or C 1 alkoxy, each optionally substituted with one to three F; and each R 5 is independently Cj alkyl optionally substituted with one to three
  • Embodiment C4 A compound of Embodiment C3 selected from the group consisting of: iV'-[2-bromo-4-[(4-methylpentyl)oxy]-5-(trifluoromethyl)phenyl]-iV-ethyl-iV- methyknethanimidamide;
  • This invention also relates to a fungicidal composition
  • a fungicidal composition comprising a fungicidally effective amount of a compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • a surfactant e.g., sodium bicarbonate
  • a solid diluent e.g., sodium bicarbonate
  • a liquid diluent e.g., sodium bicarbonate, sodium bicarbonate
  • the compounds of Formula 1 can be prepared by one or more of the following methods and variations as described in Schemes 1-5.
  • the definitions of R 1 , R 2 , R 3 , R 4 , R 5 , R 5a and A in the compounds of Formulae 1-8 below are as defined above in the Summary of the Invention.
  • a compound of Formula 1 can be prepared by reaction of a compound of Formula 2 with a halogenating agent such as JV-chlorosuccinimide, N- bromosuccinimide, iV-iodosuccinimide or their equivalent in an inert solvent such as dichloromethane or carbon tetrachloride.
  • a halogenating agent such as JV-chlorosuccinimide, N- bromosuccinimide, iV-iodosuccinimide or their equivalent in an inert solvent such as dichloromethane or carbon tetrachloride.
  • the reaction can be carried out at temperatures ranging from 0 to 110 0 C for a period of time between 1 and 48 h.
  • the reaction mixture is then allowed to come to room temperature and filtered.
  • the filtrate is washed with dilute aqueous sodium hydroxide solution, dried over a drying agent such as magnesium sulfate and then concentrated to give the compound of Formula
  • Compounds of Formula 2 can be prepared from anilines of Formula 3 as shown in Scheme 2.. A variety of methods can be used for this transformation. The following five methods are especially useful.
  • Method 1 Treatment of an aniline of Formula 3 with an acetal of formula R 1 R 2 NCH(OR 6 ⁇ 5 wherein R 6 is an alkyl. This type of transformation can be found in Toste et al., Synth. Commun., 1994, 24(11), 1617-1624.
  • a halogenating reagent such as, but not limited to, POCI 3 or SOCI 2 . This type of transformation can be found in Bergman et al., Tetrahedron, 1990, 46(17), 6058-6112.
  • Method 3 Treatment of an aniline of Formula 3 with an orthoester of formula HC(OR 6 > 3 , wherein R 6 is an alkyl, to form a corresponding iminoether, followed by heating the iminoether with an amine of formula HNR 1 R 2 .
  • This type of transformation can be found in Pissiotas et al., U.S. Patent 4,209,319.
  • This type of transformation can be found in Charles et al., World Patent Application Publication WO 2000/46184.
  • This type of transformation can be found in Charles et al., World Patent Application Publication WO 2000/46184. This method is illustrated in Step C and D of Example I, Step C and D of Example 2 and Step E and F of Example 3.
  • Compounds of Formula 3 can be prepared by reduction of the nitro group in compounds of Formula 4 as shown in Scheme 3. Many methods can be used for this reduction. Preferred methods include stannous chloride reduction in concentrated hydrochloric acid (see, for example, J. Med. Chem., 1984, 24(12), 1705-1710), iron powder reduction in a solution of acetic acid and water (see, for example, J. Org. Chem., 2001,
  • compounds of Formula 4 can be prepared by alkylation of a compound of Formula 5 with an alkylating agent of Formula 6 in the presence of a base.
  • X is a nucleophilic reaction leaving group such as, for example, bromide or iodide.
  • the reaction is conducted in the presence of at least 1 equivalent of a base, preferably from 1 to 2 equivalents.
  • Suitable bases include inorganic bases such as alkali metal hydrides (e.g., lithium hydride, sodium hydride or potassium hydride), alkali metal carbonates or alkali metal hydroxides, and organic bases such as 1,8- diazabicyclo[5.4.0]undec-7-ene.
  • a wide variety of solvents are suitable for the reaction, including, for example, but are not limited to benzene, toluene, tetrahydrofuran, dimethoxyethane, acetonitrile, i ⁇ yV-dimethylformamide as well as mixtures of these solvents.
  • the reaction is generally conducted between about -20 and 150 0 C, and preferably between 20 and 140 0 C.
  • the reaction time can range from 1 h to 7 days.
  • compounds of Formula 4 can also be prepared from compounds of Formula 7 by reacting with an appropriate alcohol of Formula 8 in the presence of a base.
  • the reaction is conducted by first treating 1 to 2 equivalents of the appropriate alcohol of Formula 8, preferably from 1 to 1.4 equivalents, with at least 1 equivalent of a base, preferably from 1 to 1.2 equivalents, for a period of time ranging from 3 minutes to 5 h followed by the addition of a compound of Formula 7.
  • Suitable bases include inorganic bases such as alkali metal hydrides (e.g., lithium hydride, sodium hydride or potassium hydride), alkali metal carbonates or alkali metal hydroxides, and organic bases such as l,8-diazabicyclo[5.4.0]undec-7-ene.
  • a phase transfer reagent such as tetrabutylammonium chloride may be employed as a catalyst for the reaction.
  • a wide variety of solvents are suitable for the reaction, such as for example, benzene, toluene, tetrahydrofuran, dimethoxyethane, acetonitrile, iV,7V-dimethylformamide, as well as mixtures of these solvents.
  • the reaction is generally conducted between about -20 and 150 0 C, and preferably between 20 and 140 0 C.
  • the reaction time can range from 1 h to 7 days. Further experimental details for the method of Scheme 5 are illustrated in Step A of Example 1.
  • compounds of Formula 4 can also be prepared from compounds of Formula 5 through a Mitsunobu reaction, which involves reaction of a compound of Formula 5 with an appropriate alcohol of Formula 8.
  • the Mitsunobu Reaction has been the subject of a number of reviews. For conditions and variations of this reaction, see the following reference and references cited therein: Hughes, Org. React., 1992, 42, 335-656. Further experimental details for the Mitsunobu reaction are illustrated in Step A of Example 2 and Step A of Example 3.
  • Step A Preparation of 1 -r(4-methylpentv ⁇ oxy1-4-nitro-2-('trifluoromethyl " )benzene To a solution of 4-methyl-l-pentanol (5.85 g, 57.2 mmol) in 1,2-dimethoxyethane
  • Step C Preparation of iV-cvano-JV-[4-[(4-methylpentyl > )oxy1-3-( ' trifluoromethyl)- phenyl]methanimidamide
  • the precipitate was collected by filtration, air dried and then dried in oven to give 1.89 g of the title compound as a white solid melting at 138-140 0 C.
  • the filtrate was concentrated, and the residue was triturated with a solution of 10 % ethyl acetate in hexanes (20 mL).
  • the precipitate was collected by filtration, air dried and then dried in oven to give an additional 0.47 g of the title compound as a white solid.
  • Step D Preparation of iV-ethyl-iV " -methyl-N " '-f4-r( r 4-methylpentyl)oxy1-3-(trifluoro- memvDphenylimethanimidamide
  • iV-cyano-iV r '-[4-[(4-methylpentyl)oxy]-3-(trifluoromethyl)phenyl]- methanimidamide (Le. the product from Step C) (2.34 g, 7.48 mmol) in acetonitrile (65 mL) at room temperature was added 7V-ethylmethylamine (3.22 mL, 37.4 mmol) dropwise.
  • Step E Preparation of N'-[2-bromo-4-f(4-methyl ⁇ entyl)oxy]-5-(trifluoromethyr)- phenyli- ⁇ -ethyl-JV ' -methylmethanirnidarnide f Compound 7)
  • Step A Preparation of r3-(2-methoxy-4-m ' trophenoxy)propyl1trimethylsilane
  • Step B Preparation of 3 -methoxy-4- [3 -(trimethylsil vDpropoxyibenzenamine
  • Step C Preparation of iV-cyano-N J -
  • iV-cyanomethanimidate 9.9 g, 101.8 mmol
  • absolute ethanol 50 mL
  • 3-methoxy-4-[3- (trimetiiylsilyl) ⁇ ropoxy]benzenamine i.e. the product from Step B
  • the reaction mixture was stirred at room temperature overnight and then concentrated.
  • Step D Preparation of iV ; -ethyl-iv 'J -
  • JV-methylmethanimidamide A mixture of iV-cyano-iV'-[3-methoxy-4-[3-(trimethylsilyl)pro ⁇ oxy]phenyl]methan- imidamide (i.e. the product from Step C) (5 g, 16.4 mmol), iV-ethylmethylamine (7 mL, 81.97 mmol) and acetonitrile (20 mL) in a Fisher-Porter bottle was heated at 130 0 C for 4 h. The resulting mixture was cooled to room temperature and then concentrated.
  • Step E Preparation of JV'-r2-bromo-5-methoxy-4-f3-( ' trimethylsilyl)propoxy1phenvn-
  • reaction mixture was then concentrated, and the residue was purified by silica gel chromatography using 50 % ethyl acetate in hexane as eluant to give 1.42 g of the title product, a compound of the present invention as a brown oil.
  • Step A Preparation of 5-nitro-2-[ " 3-rtrlmethylsilyl)propoxy1benzaldeliyde
  • diisopropyl azodicarboxylate 26 mL, 132 mmol
  • anhydrous tetrahydrofura ⁇ 500 mL
  • 2-hydroxy-5-nitrobenzaldehyde 20 g, 119.7 mmol
  • triphenylphosphine 37.7 g, 143.3 mmol
  • reaction mixture was then concentrated under reduced pressure, and the resulting precipitate was removed by filtration.
  • the filtrate was concentrated, and the residue was purified by silica gel chromatography using 10 to 20 % ethyl acetate in hexane as eluant to give 12.4 g of the title product as an oil.
  • reaction mixture was stirred at room temperature for 2 h, and an additional amount of Freon ® 22, chlorodifluoromethane (12 mL) was then added through a dry ice condenser.
  • the reaction mixture was stirred at room temperature for another 3 h, and dichloromethane (500 mL) was then added.
  • the reaction mixture was washed with water (3 x 300 mL), dried (MgSC ⁇ ), and concentrated.
  • the residue was purified by silica gel chromatography using 5 to 10 % ethyl acetate in hexane as eluant to give 7.26 g of the title product as an oil.
  • Step D Preparation of 3-rdifluoromethoxyV4-f3-trimethylsilyl]propoxy]ben2amine
  • Step E Preparation of JV-cyano-N'-f3-( ' difluoromethoxy)-4-r3-( ' trimethylsilyl)- propoxylphenyllmethanimidamide
  • Step F Preparation of Jv "> -f3-fdifluoromethoxy)-4-f3-('trimethylsilyl ' )propoxy1phenyl1-
  • n means normal, i means iso, . c means cyclo,
  • OMe means methoxy
  • OEt means ethoxy
  • the compound numbers of Tables 1 to 4 refer to compounds in Index Table A.
  • 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 (including seed coatings), and the like which can be water-dispersible (“wettable”) or water-soluble.
  • Active ingredient can be
  • 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.
  • AU 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, ⁇ iV-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, glycerol esters, poly- oxyethylene/polyoxypropylene block copolymers, and alkylpolyglycosides where the number of glucose units, referred to as degree of polymerization (D.P.), can range from 1 to 3 and the alkyl units can range from C 6 to C 14 (see Pure and Applied Chemistry 72, 1255—
  • degree of polymerization D.P.
  • 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, ⁇ yV-dimethylformamide, dimethyl sulfoxide, JV-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffins, alkylbenzenes, alkylnaphthalenes, glycerine, triacetine, 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, acetates such as hexyl acetate, heptyl acetate and octyl acetate, and alcohols such as methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfur
  • Useful formulations of this invention may also contain materials well known to those skilled in the art as formulation aids such as antifoams, film formers and dyes.
  • Antifoams can include water dispersible liquids comprising polyorganosiloxanes like Rhodorsil® 416.
  • the film formers can include polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
  • Dyes can include water dispersible liquid colorant compositions like Pro-lzed® Colorant Red.
  • formulation aids include those listed herein and those listed in McCutcheon 's 2001, Volume 2: Functional Materials published by MC Publishing Company and PCT Publication WO 03/024222.
  • 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 ⁇ A1-A%, 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. 4,172,714. 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 T. S. Woods, "The art of formulation, see T. S. Woods,
  • Example B Wettable Powder Compound 7 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Example C Wettable Powder Compound 7 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Example C Wettable Powder Compound 7 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Compound 7 25.0% hydrated attapulgite 3.0% crude calcium ligninsulfonate 10.0% sodium dihydrogen phosphate 0.5% water 61.5%.
  • Compound 7 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • the compounds of this invention are useful as plant disease control agents.
  • the present invention therefore further relates to a method for controlling plant diseases caused by 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 of Formula 1 are considered to be particularly advantageous for use on dicot (i.e., broadleaf) plants. Accordingly, the compounds of Formula 1 can be used to provide effective fungal disease control for dicot plants.
  • the compounds of Formula 1 and their fungicidal compositions are useful for controlling fungal plant disease, such as powdery mildews and rusts, caused by fungal plant pathogens in the Ascomycete, Basidiomycete and Deuteromycete classes and afflicting a wide range of ornamental, vegetable, field, cereal and fruit crops.
  • fungal plant disease such as powdery mildews and rusts
  • pathogens include: Ascomycetes, including powdery mildew diseases of cereals and broadleaf crops caused by Erysiphe spp. (including Erysiphe graminis f. sp. tritici, Erysiphe graminis f. sp.
  • hordei and Erysiphe poly gon ⁇ Uncinula necatur, Sphaerotheca fuligena, Podosphaera leucotricha and diseases caused by Helminthosporium spp. such as Helminthosporium tritici repentis, Pyren ⁇ phora teres and Rhyncosporium secalis;
  • Basidiomycetes including rust diseases of cereals and broadleaf crops caused by Puccinia spp. (such as Puccinia recondita, Puccinia striiformis, Puccinia hordei, Puccinia graminis and Puccinia arachidis), Hemileia vastatrix, Uromyces appendiculatus, Phakopsora pachyrhizi and Phakopsora meibomiae; and other genera and species related to these pathogens, including those classified in Deuteromycetes.
  • Puccinia recondita Puccinia striiformis, Puccinia hordei, Puccinia graminis and Puccinia arachidis
  • Hemileia vastatrix Uromyces appendiculatus
  • Phakopsora pachyrhizi and Phakopsora meibomiae and other genera and species related to these pathogens, including those classified in De
  • Compounds of Formula 1 can be used to control fungal diseases of a wide range of economic plants such as alfalfa, barley, cotton, wheat, rape, sugarbeets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables including lettuce, garden beets, peas, beans, carrots, cole crops, curcurbit crops, tomato and pepper, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, grapes, citrus (e.g., orange, tangerine, lemon, lime, grapefruit), apple, cherry, pear, peach, apricot and other fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass).
  • turf species e.g., Kentucky bluegrass, St. August
  • 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, 3-bromo-l-(3-chloro-2 ⁇ pyridmyl)-N-[4-cyano-2-methyl- 6-[(methylamino)carbonyl] ⁇ henyl]-lH-pyrazole-5-carboxamide, buprofezin, ⁇ carbofuran, chlorfenapyr, chlorantraniliprole, chlorpyrifos, chlorpyrifos-methyl, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, difiubenzuron, dimefluthrin, dimethoate, dinotefuran, esfenvaler
  • insecticides such as abamectin, acep
  • fungicides such as acibenzolar, aldimorph, amisulbrom, azaconazole, azoxystrobin, benalaxyl, benomyl, benthiavalicarb, benthiavalicarb-isopropyl, binomial, biphenyl, bitertanol, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), boscalid/nicobifen, bromuconazole, bupirimate, buthiobate, carboxin, carpropamid,
  • the weight ratios of these various mixing partners to compounds of this invention typically are between 100:1 and 1:100, preferably between 30:1 and 1:30, more preferably between 10:1 and 1:10, and most preferably between 4:1 and 1:4.
  • a compound of Formula 1 e.g., Compound 15
  • azoxystrobin kresoxim-methyl
  • trifloxystrobin pyraclostrobin
  • picoxystrobin dimoxystrobin, metominostrobin/fenominostrobin, carbendazim, chlorothalonil, quinoxyfen, metrafenone, cyflufenamid, fam ⁇ xadone, fenpropidin, fenpropimorph, fluoxastrobin, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, flusilazole, hexaconazole, ipconazole, metconazole, penconazole, propiconazole, proquinazid, prothioconazole, tebuconazole, triticonazole, prochloraz or boscalid/nicobifen.
  • Preferred for better control of plant diseases caused by fungal plant pathogens are mixtures of a compound of Formula 1 with a fungicide selected from the group: azoxystrobin, fluoxastrobin, kresoxim-methyl, trifloxystrobin, pyraclostrobin, picoxystrobin, dimoxystrobin, metominostrobin/fenominostrobin, quinoxyfen, metrafenone, cyflufenamid, fenpropidin, fenpropimorph, cyproconazole, epoxiconazole, flusilazole, metconazole, propiconazole, famoxadone, proquinazid, prothioconazole, tebuconazole and triticonazole.
  • azoxystrobin fluoxastrobin, kresoxim-methyl, trifloxystrobin, pyraclostrobin, picoxystrobin, dimoxystrobin, metomin
  • Specifically preferred mixtures are selected from the group: the combinations of Compound 7, Compound 8, Compound 15, Compound 22 or Compound 25 with azoxystrobin, the combinations of Compound 7, Compound 8, Compound 15, Compound 22 or Compound 25 with fluoxastrobin, the combinations of Compound 7, Compound 8, Compound 15, Compound 22 or Compound 25 with kresoxim-methyl, the combinations of Compound 7, Compound 8, Compound 15, Compound 22 or Compound 25 with trifloxystrobin, the combinations of
  • Phakopsora pachyrhizi which comprise applying a combination of a compound of Formula 1 (e.g., Compound 7, 8, 15, 22 or 25) with at least one compound selected from triazole fungicides that inhibit demethylase in sterol biosynthesis (e.g., cyproconazole, flusilazole and/or tebuconazole).
  • fungicidal compositions comprising a compound of Formula 1 (e.g., Compound 7, 8, 15, 22 or 25) and at least one compound selected from triazole fungicides that inhibit demethylase in sterol biosynthesis (e.g., cyproconazole, flusilazole and/or tebuconazole).
  • Plant disease control preventatively and curatively, 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 1O g per kilogram of seed.
  • TESTS demonstrate the control efficacy of compounds of this invention on specific pathogens.
  • the pathogen control protection afforded by the compounds is not limited, however, to these species. See Index Tables A-B for compound descriptions. The following abbreviations are used in the Index Tables which follow: Me means methyl, Et means ethyl, Pr means propyl, ra-Pr means normal propyl, i-P ⁇ means isopropyl, OMe means methoxy, OEt means ethoxy.
  • the abbreviation "Ex.” stands for "Example” and is followed by a number indicating in which example the compound is prepared.
  • Test compounds were first dissolved in acetone in an amount equal to 3 % of the final volume and then suspended at the desired concentration (in ppm) in acetone and purified water (50/50 mix) containing 250 ppm of the surfactant Trem® 014 (polyhydric alcohol esters). The resulting test suspensions were then used in the following tests.
  • test suspension was sprayed at 40 ppm (equivalent to a rate of 120 g/ha) to the point of run-off on wheat seedlings.
  • seedlings were inoculated with a spore suspension of Puccinia recondita (the causal agent of wheat brown rust) and incubated in a saturated atmosphere at 20 0 C for 24 h, and then moved to a growth chamber at 20 0 C for 6 days, after which time disease ratings were made.
  • test suspension was sprayed at 40 ppm (equivalent to a rate of 120 g/ha) to the point of run-off on wheat seedlings.
  • seedlings were inoculated with a spore dust of Erysiphe graminis f. sp. tritid, (the causal agent of wheat powdery mildew) and incubated in a growth chamber at 20 0 C for 7 days, after which time disease ratings were made.
  • test suspension was sprayed at 20 g/ha (in an application volume of 1000 L/ha) on grape seedlings. The following day the seedlings were inoculated with a spore suspension of Uncinula necatur (the causal agent of grape powdery mildew) and incubated in a greenhouse at 20 0 C for 14 days, after which time disease ratings were made.
  • test suspension was sprayed at 100 g/ha (in an application volume of 1000 L/ha) on soybean seedlings. The following day the seedlings were incubated in a saturated atmosphere at 20 0 C for 48 h and then moved to a growth chamber at 22 0 C for 14 days, after which time crop safety ratings were made.
  • test suspension was sprayed at 20 g/ha (in an application volume of 1000 L/ha) on soybean seedlings. The following day the seedlings were incubated in a saturated atmosphere at 20 0 C for 48 h and then moved to a growth chamber at 22 0 C for 14 days, after which time crop safety ratings were made.
  • Results for Tests A-E are given in Table A.
  • disease efficacy ratings are based on the percent leaf area with no visible symptoms, expressed as a percent (0 to 100 %) of total leaf area — e.g., 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.
  • crop safety ratings are based on the percent leaf area showing injury, expressed as a percent (0 to 100 %) of total leaf area — e.g., a rating of 100 indicates 100 % crop injury and a rating of 0 indicates no crop injury.
  • Tests A-E show compounds that are effective at controlling rust and powdery mildew diseases of cereal and broadleaf crops, and are advantageous for use on broadleaved crops.
  • the compound numbers of Table A refer to compounds in Index Table A. Table A
  • Results are given in Table B. Disease efficacy ratings are expressed as a percent (0 to 100 %) of total leaf area - e.g., a rating of 100 indicates 100 % disease control and a rating of 0 indicates no disease control (relative to the controls). "DATl" refers to the number of days after the first spray application (Tl). The compound numbers of Table B refer to compounds in Index Table A.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Cette invention concerne des composés représentés par la formule 1, et leurs N-oxydes et leurs sels adaptés à l'agriculture. Ces composés peuvent être utilisés comme fongicides et sont représentés par la formule (1), dans cette formule R1 représente C1 C4 alkyle ou C3 C4 cycloalkyle; R2 représente C1 C3 alkyle; R3 représente Br, Cl ou I; R4 représente Cl; ou C1 C2 alkyle ou C1 C2 alkoxy, chacun étant éventuellement substitué par un, deux ou trois substituants choisis indépendamment dans le groupe halogène; A représente C ou Si; chaque R5 représente C1 C2 alkyle éventuellement substitué avec un, deux ou trois substituants choisis indépendamment dans le groupe halogène; et R5a représente H ou C1 C2 alkyle; sous réserve que lorsque A représente Si, R5a représente C1 C2 alkyle. Cette invention concerne également des compositions comprenant les composés représentés par la formule (1), ainsi que des méthodes permettant de lutter contre les maladies de végétaux provoquées par des agents pathogènes de végétaux fongiques, lesquelles méthodes consistent à appliquer une quantité efficace d'un composé représenté par la formule (1).
PCT/US2006/044924 2005-11-23 2006-11-20 Composes amidinylphenyle et utilisation de ceux-ci en comme fongicides Ceased WO2007061966A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US73962705P 2005-11-23 2005-11-23
US60/739,627 2005-11-23

Publications (2)

Publication Number Publication Date
WO2007061966A2 true WO2007061966A2 (fr) 2007-05-31
WO2007061966A3 WO2007061966A3 (fr) 2007-07-12

Family

ID=37946278

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/044924 Ceased WO2007061966A2 (fr) 2005-11-23 2006-11-20 Composes amidinylphenyle et utilisation de ceux-ci en comme fongicides

Country Status (4)

Country Link
AR (1) AR057929A1 (fr)
PE (1) PE20070822A1 (fr)
TW (1) TW200804245A (fr)
WO (1) WO2007061966A2 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20101575A1 (it) * 2010-08-26 2012-02-27 Isagro Ricerca Srl Fenilammidine ad elevata attivita' fungicida e relativo uso
WO2012060401A1 (fr) 2010-11-05 2012-05-10 大塚アグリテクノ株式会社 Éthynylphénylamidine ou l'un de ses sels, son procédé de production et fongicide pour applications agricoles et horticoles
WO2016202688A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
EP3335559A1 (fr) 2016-12-14 2018-06-20 Bayer CropScience Aktiengesellschaft Combinaisons de composés actifs
WO2018109002A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs
WO2018108998A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Phénylamidines et leur utilisation en tant que fongicides
WO2018108992A2 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines et leur utilisation en tant que fongicides
WO2018193385A1 (fr) 2017-04-20 2018-10-25 Pi Industries Ltd. Nouveaux composés de phénylamine
WO2018211442A1 (fr) 2017-05-18 2018-11-22 Pi Industries Ltd. Composés de formimidamidine utiles contre des micro-organismes phytopathogènes
EP3708565A1 (fr) 2020-03-04 2020-09-16 Bayer AG Pyrimidinyloxyphénylamidines et leur utilisation comme fongicides
US10912297B2 (en) 2015-07-08 2021-02-09 Bayer Cropscience Aktiengesellschaft Phenoxyhalogenphenylamidines and the use thereof as fungicides
EP3915971A1 (fr) 2020-12-16 2021-12-01 Bayer Aktiengesellschaft Phényl-s(o)n-phénylamidines et leur utilisation comme fongicides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR0309599A (pt) * 2002-05-03 2005-03-01 Du Pont Composto, composições fungicidas e método para o controle de doenças vegetais
AU2005251750A1 (en) * 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Fungicidal mixtures of amidinylphenyl compounds

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20101575A1 (it) * 2010-08-26 2012-02-27 Isagro Ricerca Srl Fenilammidine ad elevata attivita' fungicida e relativo uso
WO2012060401A1 (fr) 2010-11-05 2012-05-10 大塚アグリテクノ株式会社 Éthynylphénylamidine ou l'un de ses sels, son procédé de production et fongicide pour applications agricoles et horticoles
US8785649B2 (en) 2010-11-05 2014-07-22 Otsuka Agritechno Co., Ltd. Ethynylphenylamidine compound or salt thereof, method for producing same, and fungicide for agricultural and horticultural use
US9169276B2 (en) 2010-11-05 2015-10-27 Otsuka Agritechno Co., Ltd. Ethynylphenylamidine compound or salt thereof, method for producing same, and fungicide for agricultural and horticultural use
US10252977B2 (en) 2015-06-15 2019-04-09 Bayer Cropscience Aktiengesellschaft Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides
WO2016202688A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
US10506807B2 (en) 2015-06-15 2019-12-17 Bayer Cropscience Aktiengesellschaft Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides
US10912297B2 (en) 2015-07-08 2021-02-09 Bayer Cropscience Aktiengesellschaft Phenoxyhalogenphenylamidines and the use thereof as fungicides
WO2018108998A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Phénylamidines et leur utilisation en tant que fongicides
WO2018108977A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs
WO2018108992A2 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines et leur utilisation en tant que fongicides
WO2018109002A1 (fr) 2016-12-14 2018-06-21 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs
EP3335559A1 (fr) 2016-12-14 2018-06-20 Bayer CropScience Aktiengesellschaft Combinaisons de composés actifs
WO2018193385A1 (fr) 2017-04-20 2018-10-25 Pi Industries Ltd. Nouveaux composés de phénylamine
US11524934B2 (en) 2017-04-20 2022-12-13 Pi Industries Ltd Phenylamine compounds
WO2018211442A1 (fr) 2017-05-18 2018-11-22 Pi Industries Ltd. Composés de formimidamidine utiles contre des micro-organismes phytopathogènes
EP3708565A1 (fr) 2020-03-04 2020-09-16 Bayer AG Pyrimidinyloxyphénylamidines et leur utilisation comme fongicides
EP3915971A1 (fr) 2020-12-16 2021-12-01 Bayer Aktiengesellschaft Phényl-s(o)n-phénylamidines et leur utilisation comme fongicides

Also Published As

Publication number Publication date
AR057929A1 (es) 2007-12-26
PE20070822A1 (es) 2007-08-16
WO2007061966A3 (fr) 2007-07-12
TW200804245A (en) 2008-01-16

Similar Documents

Publication Publication Date Title
JP7487364B2 (ja) 殺真菌性オキサジアゾール
EP2217600B1 (fr) Pyrazoles bicycliques fongicides
EP2121660B1 (fr) Amides fongicides
US20050182025A1 (en) Amidinylphenyl compounds and their use as fungicides
CN115955916A (zh) 活性化合物组合
EP2867228B1 (fr) Carboxamides hétérocycliques fongicides
DK2427058T3 (en) nematicidal SULPHONAMIDES
EP2521450B1 (fr) Composés hétérocycliques fongicides
CN113260610A (zh) 取代的甲苯基杀真菌剂
US8026359B2 (en) Fungicidal heterocyclic amines
WO2005120234A2 (fr) Melanges fongicides de composes d'amidinylphenyle
TW201418223A (zh) 經取代之甲苯基殺真菌劑
MX2013002400A (es) Pirazoles fungicidas.
WO2010093595A1 (fr) 2‑pyridones fongicides
US20150336985A1 (en) Fungicidal heterocyclic compounds
US20110092544A1 (en) Fungicidal pyridines
AU2010341457A1 (en) Fungicidal 2-(bicyclic aryloxy)carboxamides
TW200804245A (en) Amidinylphenyl compounds and their use as fungicides
US20050020644A1 (en) Bicyclic fused pyridinyl amides and advantagesous compositons thereof for use as fungicides
CN105683164A (zh) 杀真菌吡唑类
JP2008530231A (ja) 殺菌・殺カビ性ピラジン誘導体
WO2003103393A1 (fr) Melanges de pyrimidinones et de composes dinitrophenoliques utiles pour lutter contre l'oidium
US20140235689A1 (en) Fungicidal pyrazoles

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06844442

Country of ref document: EP

Kind code of ref document: A2