Patents by Inventor Josef Ehrenfreund
Josef Ehrenfreund has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 7618952Abstract: Fungicidal compounds of formula (I): where X is O or S; RING is phenyl or thienyl; Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by one to four groups R4; R1 is hydrogen, optionally substituted (C1-4)alkyl, formyl, optionally substituted (C1-4)alkylC(?O), optionally substituted (C1-4)alkylC(?O)O, optionally substituted (C1-4)alkoxy(C1-4)alkyl, optionally substituted allyl, optionally substituted propargyl or optionally substituted allenyl; each R2 is, independently, halogen, optionally substituted (C1-4)alkyl, optionally substituted (C1-4)alkoxy or optionally substituted (C1-4)alkoxy(C1-4)alkyl; R3 is (CRaRb)m—Cy—(CRCRd)n—Y; each R4 is, independently, selected from halogen, C1-3 alkyl, C1-3 haloalkyl, C1-3alkoxy(C1-3)alkyl and cyano; Ra, Rb, Rc and Rd are each, independently, hydrogen or optionally substituted (C1-4)alkyl; Cy is an optionally substituted carbocyclic or heterocyclic 3-7Type: GrantFiled: September 8, 2004Date of Patent: November 17, 2009Assignee: Syngenta Crop Protection, Inc.Inventors: Josef Ehrenfreund, Clemens Lamberth, Hans Tobler, Harald Walter
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Patent number: 7598395Abstract: The invention relates to a fungicidally active compound of formula (I): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, provided that the ring is not 1,2,3-triazole, the ring being substituted by groups R8, R9 and R10; X is a single or double bond; Y is O, S, N(R11) or (CR12R13)(CR14R15)m(CR16R17)n; m is 0 or 1; n is 0 or 1; and R1 to R17 each, independently, have a range of values; to the preparation of these compounds, to novel intermediates used in the preparation of these compounds, to agrochemical compositions which comprise at least one of the novel compounds as active ingredient, to the preparation of the compositions mentioned and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.Type: GrantFiled: October 14, 2003Date of Patent: October 6, 2009Assignee: Syngenta Crop Protection, Inc.Inventors: Josef Ehrenfreund, Hans Tobler, Harald Walter
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Publication number: 20090221856Abstract: The present invention relates to a novel a process for the preparation of the compound of the general formula (I), wherein R1 and R2 are independently H or C1-6 alkyl, which comprises treating with a reducing agent either a compound of the general formula (II), wherein R1 and R2 have the meanings given for the compound of the formula (I), R3 is H or C1-4alkyl and Ph is phenyl, or a compound of the general formula (III), wherein R1, R2, R3 and Ph have the meanings given for the compound of the formula (II), the reducing agent being effective to cleave the benzyl moiety Ph-CH(R3)— from the benzylamino moiety PhCH(R3)NH— in the compound of the formula (II) or in the compound of the formula (III) to leave an amino group and, in addition, in the case of the compound of the formula (III), to reduce both the 2,3-double bond and the double bond joining the R1R2C— moiety to the 9-position of the benzonorbornene ring to single bonds.Type: ApplicationFiled: December 11, 2006Publication date: September 3, 2009Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Hans Tobler, Harald Walter, Camilla Corsi, Josef Ehrenfreund, Fanny Giordano, Martin Zeller
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Publication number: 20090221855Abstract: The present invention relates to a process for the preparation of compounds of formula wherein R1, R2 and R3 are each independently of the others hydrogen or C1-C4alkyl, by a) reacting compounds of formula (II) wherein R1, R2 and R3 are as defined for formula (I) and X is bromine or chlorine, with a compound of formula (III) wherein R4 is hydrogen or C1-C4alkyl, in the presence of a base and catalytic amounts of at least one palladium complex compound, to form compounds of formula (IV) wherein R1, R2, R3 and R4 are as defined for formula (I), and b) converting those compounds, using a reducing agent, into compounds of formula (I).Type: ApplicationFiled: August 28, 2006Publication date: September 3, 2009Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Hans Tobler
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Patent number: 7582589Abstract: The invention also relates to novel compounds of formula (1) where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by one to three groups R4; R1 is hydrogen, optionally substituted (C1-4)alkyl, formyl, optionally substituted (C1-4)alkylC(?O), optionally substituted (C1-4)alkylC(?O)O, optionally substituted (C1-4)alkoxy(C1-4)alkyl, optionally substituted allyl, optionally substituted propargyl or optionally substituted allenyl; each R2 is, independently, halogen, optionally substituted (C1-4)alkyl, optionally substituted (C1-4)alkoxy or optionally substituted (C1-4)alkoxy(C1-4)alkyl; R3 is either at position 2 or at position 4 of the thiophene ring and is an organic group containing three to thirteen carbon atoms and at least one silicon atom and, optionally, one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, and is optionally substituted by one to fouType: GrantFiled: April 21, 2004Date of Patent: September 1, 2009Assignee: Syngenta Crop Protection, Inc.Inventors: Josef Ehrenfreund, Harald Walter, Hans Tobler, Clemens Lamberth
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Publication number: 20090216027Abstract: A compound of formula (I): where A is an ortho-substituted ring selected from a number of specified rings; R1 is halogen, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy or optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl or optionally substituted SO2(C1-4)alkyl (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen and C1-4 alkoxy); R2 is C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4)alkyl or C1-4 alkylthio(C1-4)alkyl or [optionally substituted aryl](C1-4)alkyl- or [optionally substituted aryl]oxy(C1-4)alkyl-(where the optionally substituted aryl moieties may each have up to 3 substituents, each independently selected from halogen and C1-4 alkoxy); R3 is hydrogen, CH2C?CR4, CH2CR4?C(H)R4, CH?C?CH2 or COR5 or optionally substituted C1-4 alkyl, optionally substituted C1-4 alkoxy or optionally substituted (C1-4) alkylC(?O)O (where the optionally substituted moieties may each have up to 3 substitType: ApplicationFiled: May 11, 2009Publication date: August 27, 2009Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Josef Ehrenfreund, Hans Tobler, Harald Walter
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Publication number: 20090197925Abstract: A compound of formula (I): Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by groups R4, R5 and R6; R1 is hydrogen or halo; R2 is hydrogen or halo; R3 is optionally substituted C2-12 alkyl, optionally substituted C2-12 alkenyl, optionally substituted C2-12 alkynyl, optionally substituted C3-12 cycloalkyl, optionally substituted phenyl or optionally substituted heterocyclyl; and R4, R5 and R6 are, independently, selected from hydrogen, halo, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4)alkyl and C1-4 haloalkoxy(C1-4)alkyl, provided that at least one of R4, R5 and R6 is not hydrogen. The compounds of formula (I) have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms.Type: ApplicationFiled: April 8, 2009Publication date: August 6, 2009Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Josef Ehrenfreund, Hans Tobler, Harald Walter
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Publication number: 20090177011Abstract: The present invention relates to a process for the preparation of compounds of formula (I) wherein R1, R2 and R3 are each independently of the others hydrogen or methyl, by reaction of compounds of formula (II) wherein R1, R2 and R3 are as defined for formula (I) and X is bromine or chlorine, with ammonia in the presence of a catalytic amount of at least one copper-containing compound.Type: ApplicationFiled: December 8, 2005Publication date: July 9, 2009Applicant: Syngenta Crop Protection, Inc.Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Clemens Lamberth, Hans Tobler
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Patent number: 7553798Abstract: Compounds of the formula (I), in which the substituents are as defined in claim 1 are suitable for use as microbiocides.Type: GrantFiled: June 21, 2005Date of Patent: June 30, 2009Assignee: Syngenta Crop Protection, Inc.Inventors: Clemens Lamberth, Camilla Corsi, Josef Ehrenfreund, Hans Tobler, Harald Walter
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Publication number: 20090163569Abstract: The present invention relates to a process for the preparation of compounds of formula (I) wherein R1 and R2 are each independently of the other hydrogen or C1-C5alkyl and R3 is CF3 or CF2H, by a) reaction of a compound of formula (II) wherein R1 and R2 are as defined for formula (I), with at least one reducing agent to form a compound of formula (III) wherein R1 and R2 are as defined for formula (I), and b) reaction of that compound with at least one reducing agent to form a compound of formula (IV) wherein R1 and R2 are as defined for formula (I), and (c) reaction of that compound with a compound of formula (V) wherein Q is chlorine, fluorine, bromine, iodine, hydroxy or C1-C6alkoxy and R3 is as defined for formula (I), to form the compound of formula (I); and to novel intermediates for use in that process.Type: ApplicationFiled: September 14, 2006Publication date: June 25, 2009Applicants: SYNGENTA CROP PROTECTION, INC., SYNGENTA LIMITEDInventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi, Fanny Giordano, Martin Zeller, Gottfried Seifert, Shailesh Shah, Neil George, Ian Kevin Jones, Paul Edward Bonnett
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Patent number: 7531559Abstract: A compound of formula (I):, where A is an ortho-substituted ring selected from a number of specified rings; R1 is halogen, cyano, nitro, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy or optionally substituted C2-4 alkenyl, optionally substituted C2-4 alkynyl or optionally substituted SO2(C1-4 alkyl) (where the optionally substituted moieties may each have up to 3 substituents, each independently selected from halogen and C1-4 alkoxy); R2 is C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy(C1-4)alkyl or C1-4 alkylthio(C1-4)alkyl or [optionally substituted aryl](C1-4)alkyl- or [optionally substituted aryl]oxy(C1-4)alkyl (where the optionally substituted aryl moieties may each have up to 3 substituents, each independently selected from halogen and C1-4 alkoxy); R3 is hydrogen, CH2C?CR4, CH2CR4?C(H)R4, CH?C?CH2 or COR5 or optionally substituted C1-4 alkyl, optionally substituted C1-4 alkoxy or optionally substituted (C1-4)alkylC(?O)O (where the optionally substituted moieties may each have up to 3 substituentType: GrantFiled: August 18, 2003Date of Patent: May 12, 2009Assignee: Syngenta Crop Protection, Inc.Inventors: Josef Ehrenfreund, Hans Tobler, Harald Walter
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Patent number: 7514584Abstract: The present invention relates to a process for the preparation of compounds of formula (I) wherein the substituents are as defined in claim 1, by a) reaction of a compound of formula (II) to form a compound of formula (III) b) reaction of that compound in the presence of a base to form a compound of formula (IV) c) conversion of that compound in the presence of a reducing agent into a compound of formula (I).Type: GrantFiled: February 20, 2006Date of Patent: April 7, 2009Assignee: Syngenta Crop Protection, Inc.Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Clemens Lamberth, Hermann Schneider, Hans Tobler
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Publication number: 20090069572Abstract: The present invention relates to a process for the preparation of compounds of formula I wherein R1 is C1-C4haloalkyl; R2 is C1-C6alkyl and R3 is methyl or ethyl, by reaction of compounds of formula II wherein the substituents are as defined for formula I, with compounds of formula III wherein R3 is as defined for formula I and n is 0 or 1.Type: ApplicationFiled: October 19, 2005Publication date: March 12, 2009Applicant: Syngenta Crop Protection, Inc.Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Clemens Lamberth, Hans Tobler
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Publication number: 20090054496Abstract: The invention relates to a fungicidally active compound of the general Formula (I): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by the groups R3, R4 and R5; R1 and R2 are independently H, halo, C1-4 alkyl or C1-4 haloalkyl; and R3, R4 and R5 are each, independently, H, halo, C1-4 alkyl, C1-4 haloalkyl or C1-4 haloalkoxy, provided that at least one of R3, R4 and R5 is not H; to the preparation of these compounds, to novel intermediates used in their preparation, to agrochemical compositions which comprise at least one of the novel compounds as an active ingredient, to the preparation of the compositions and to the use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestations of plants by phytopathogenic microorganisms, especially fungi.Type: ApplicationFiled: November 13, 2005Publication date: February 26, 2009Applicant: Syngenta Crop Protection, Inc.Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Hans Tobler
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Publication number: 20090054233Abstract: A method of controlling phytopathogenic diseases on useful plants or plant propagation material thereof, which comprises applying to said plant propagation material a fungicidally effective amount of a compound of formula (I) wherein R1 is trifluoromethyl or difluoromethyl and R2 is hydrogen or methyl, or a tautomer of such a compound, is particularly effective in controlling or preventing fungal diseases of crop plants.Type: ApplicationFiled: August 11, 2005Publication date: February 26, 2009Inventors: Harald Walter, Ronald Zeun, Josef Ehrenfreund, Hans Tobler, Camilla Corsi, Clemens Lamberth
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Publication number: 20090030233Abstract: The present invention relates to a novel process for the preparation of a compound of formula (I): which comprises reacting a compound of formula (II): with a compound of general formula (III): wherein R1 and R2 are H or C1-4 alkyl or R1 and R2 join together to form a C2-3 alkylene group, which is optionally substituted by from 1 to 4 methyl or ethyl groups, or an anhydride of the compound (III), in the presence of a base and of a palladium catalyst which is (a) a palladium (0)- or palladium (II)-triarylphosphine complex optionally in the presence of additional amounts of a triarylphoshine ligand, or (b) a palladium (II) salt in the presence of a triarylphosphine ligand, or (c) metallic palladium, optionally deposited on a support, in the presence of triarylphosphine; there being used from 0.9 to 2 moles of compound (III) for each mole of compound (II).Type: ApplicationFiled: November 13, 2006Publication date: January 29, 2009Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Josef Ehrenfreund, Harald Walter, Hans Tobler, Camilla Corsi
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Publication number: 20080262242Abstract: The present invention relates to a novel process for the preparation of a compound of general formula (I): wherein R1 is H or C1-4 alkyl and R2 is difluoromethyl or trifluoromethyl, which comprises reacting a compound of general formula (II): wherein R1 has the meaning given above and X is chloro or bromo, with a compound of general formula (III): wherein R2 has the meaning given above, in the presence of a base, a palladium catalyst and a ferrocenyl biphoshine ligand of the Josiphos type, the reaction being carried out in an ether solvent at a reflux temperature of at least 100° C.Type: ApplicationFiled: November 13, 2006Publication date: October 23, 2008Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Hans Tobler
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Publication number: 20080227835Abstract: The invention relates to a fungicidally active compound of formula (I): where Het is a 5- or 6-membered heterocyclic ring containing one to three heteroatoms, each independently selected from oxygen, nitrogen and sulphur, the ring being substituted by the groups R6, R7 and R8; R1 is hydrogen, C1-4alkyl, C1-4haloalkyl, C1-4alkoxy, C1-4haloalkoxy, CH2C?CR9, CH2CR10?CHR11, CH?C?CH2 or COR12; R2 and R3 are each, independently, hydrogen, halo, C1-4alkyl, C1-4 alkoxy, C1-4 haloalkyl or C1-4haloalkoxy; R4 and R5 are each independently selected from halo, cyano and nitro; or one of R4 and R5 is hydrogen and the other is selected from halo, cyano and nitro; R6, R7 and R8 are each, independently, hydrogen, halo, cyano, nitro, C1-4alkyl, C1-4haloalkyl, C1-4 alkoxy(C1-4)alkyl, C1-4 haloalkoxy(C1-4)alkyl or C1-4 haloalkoxy, provided that at least one of R6, R7 and R8 is not hydrogen; R9, R10 and R11 are each, independently, hydrogen, halo, C1-4 alkyl, C1-4 haloalkyl or C1-4 alkoxy(C1-4)alkyl; and R12 is hydrogen, C1-6 alkType: ApplicationFiled: October 23, 2006Publication date: September 18, 2008Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Hans Tobler, Harald Walter, Josef Ehrenfreund, Camilla Corsi
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Publication number: 20080214532Abstract: Compounds of the formula (I) in which the substituents are as defined in claim 1 are suitable for use as microbiocides.Type: ApplicationFiled: March 21, 2006Publication date: September 4, 2008Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Clemens Lamberth, Hans Tobler
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Publication number: 20080188442Abstract: Compounds of the formula I in which the substituents are as defined in claim 1 are suitable for use as microbiocides.Type: ApplicationFiled: July 17, 2006Publication date: August 7, 2008Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Clemens Lamberth, Camilla Corsi, Josef Ehrenfreund, Hans Tobler, Harald Walter