Patents by Inventor Helmars Smits
Helmars Smits 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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Publication number: 20170217953Abstract: The present invention relates to a process for the preparation of a compound of formula (I) wherein A1 and A2 are C—H, or one of A1 and A2 is C—H and the other is N; R1 is C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl; each R2 is independently bromo, chloro, fluoro or trifluoromethyl; R3 is hydrogen; R4 is hydrogen, halogen, methyl, halomethyl or cyano; or R3 and R4 together form a bridging 1,3-butadiene group; R5 is chlorodifluoro-methyl or trifluoromethyl; n is 2 or 3; by reacting a compound of formula (II) wherein A1, A2, R1, R2, R3, R4, R5 and n is as defined under formula (I) above, with hydroxylamine, a base and a chiral catalyst, characterized in that the chiral catalyst is a dimeric chiral catalyst of formula (III) wherein R6, R7, R8, R9, R10 and X are as defmed in claim 1.Type: ApplicationFiled: August 4, 2015Publication date: August 3, 2017Applicant: Syngenta Participations AGInventors: Tomas SMEJKAL, Helmars SMITS
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Patent number: 9718762Abstract: The present invention relates to novel triazole derivatives of formula (I) having insecticidal activity, to processes and intermediates for preparing them, to insecticidal, acaricidal, nematicidal or molluscicidal compositions comprising them and to methods of using them to combat and control insect, acarine, nematode or mollusc pests; wherein R1, R2, G1, G2, Q1 and Q2 are as defined in claim 1; or salts thereof.Type: GrantFiled: October 24, 2013Date of Patent: August 1, 2017Assignee: Syngenta Participations AGInventors: Ottmar Franz Hueter, Pierre Joseph Marcel Jung, Thomas Pitterna, Helmars Smits, Andre Stoller
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Publication number: 20170204072Abstract: The present invention relates to processes for the preparation of substituted cycloserine compounds of formula (I) wherein R1 is C1-C8alkyl, C1-C8haloalkyl, C3-C6 cycloalkyl, aryl or aryl substituted by one to five R11, or aryl-C1-C4alkylene or aryl-C1-C4alkylene substituted by one to five R11; and each R11 is independently C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, cyano or halogen; The invention also relates to intermediates produced by the processes. Compounds of formula (I) are useful intermediates for the production of compounds in the agricultural and pharmaceutical fields.Type: ApplicationFiled: April 3, 2017Publication date: July 20, 2017Applicant: Syngenta Participations AGInventors: Tomas SMEJKAL, Helmars SMITS, Christian LOTHSCHUETZ, Miroslav TERINEK
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Patent number: 9643938Abstract: The present invention relates to processes for the preparation of substituted cycloserine compounds of formula (I) wherein R1 is C1-C8alkyl, C1-C8haloalkyl, C3-C6cycloalkyl, aryl or aryl substituted by one to five R11, or aryl-C1-C4alkylene or aryl-C1-C4alkylene substituted by one to five R11; and each R11 is independently C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, cyano or halogen; The invention also relates to intermediates produced by the processes. Compounds of formula (I) are useful intermediates for the production of compounds in the agricultural and pharmaceutical fields.Type: GrantFiled: April 30, 2015Date of Patent: May 9, 2017Assignee: Syngenta Participations AGInventors: Tomas Smejkal, Helmars Smits, Christian Lothschuetz, Miroslav Terinek
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Patent number: 9598369Abstract: The present invention provides a novel and improved process for the production of the production of hindered anilines containing perfluoroalky groups in good yield any by using close to stoichiometric amounts of acylating agent.Type: GrantFiled: April 1, 2014Date of Patent: March 21, 2017Assignee: Syngenta Participations AGInventors: Helmars Smits, Thomas Pitterna, Ottmar Franz Hueter, Andrew Edmunds, Andre Stoller, Pierre Joseph Marcel Jung
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Publication number: 20170044116Abstract: The present invention relates to processes for the preparation of substituted cycloserine compounds of formula (I) wherein R1 is C1-C8alkyl, C1-C8haloalkyl, C3-C6cycloalkyl, aryl or aryl substituted by one to five R11, or aryl-C1-C4alkylene or aryl-C1-C4alkylene substituted by one to five R11; and each R11 is independently C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, cyano or halogen; The invention also relates to intermediates produced by the processes. Compounds of formula (I) are useful intermediates for the production of compounds in the agricultural and pharmaceutical fields.Type: ApplicationFiled: April 30, 2015Publication date: February 16, 2017Applicant: Syngenta Participations AGInventors: Tomas SMEJKAL, Helmars SMITS, Christian LOTHSCHUETZ, Miroslav TERINEK
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Patent number: 9469633Abstract: The present invention relates to processes for the enantio-selective preparation of spyrrolidine derivatives useful in the manufacture of pesticidally active compounds, as well as to intermediates in the processes. The processes include those comprising (a-i) reacting a compound of formula Ia wherein P is alkyl, aryl or heteroaryl, each optionally substituted, wherein the heteroaryl is connected at P via a ring carbon atom; R1 is chlorodifluoromethyl or trifluoromethyl; R2 is aryl or heteroaryl, each optionally substituted; with a source of cyanide in the presence a chiral catalyst to give a compound of formula IIa wherein P, R1 and R2 are as defined for the compound of formula Ia; and (a-ii) oxidizing the compound of formula IIa with a peroxy acid, or peroxide in the presence of an acid to give a compound of formula VI wherein R1 and R2 are as defined for the compound of formula Ia.Type: GrantFiled: September 28, 2012Date of Patent: October 18, 2016Assignee: Syngenta Participations AGInventors: Tomas Smejkal, Helmars Smits, Sebastian Volker Wendeborn, Guillaume Berthon, Jerome Yves Cassayre, Myriem El Qacemi
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Publication number: 20160168097Abstract: The present invention provides a novel and improved process for the production of the production of hindered anilines containing perfluoroalky groups in good yield any by using close to stoichiometric amounts of acylating agent.Type: ApplicationFiled: April 1, 2014Publication date: June 16, 2016Applicant: Syngenta Participations AGInventors: Helmars Smits, Thomas Pitterna, Ottmar Franz Hueter, Andrew Edmunds, Andre Stoller, Pierre Joseph Marcel Jung
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Publication number: 20160159799Abstract: A process for making certain spiroheterocyclic pyrrolidine dione derivatives.Type: ApplicationFiled: July 11, 2014Publication date: June 9, 2016Applicant: SYNGENTA PARTICIPATIONS AGInventors: Edouard Godineau, Tomas Smejkal, Sophie Pelletier, Michel Muehlebach, Regis Jean Georges Mondiere, Helmars Smits, Jochen Weckesser, Alan James Robinson
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Publication number: 20160073631Abstract: The present invention provides stereoselective processes for the preparation of compounds of formula (I) wherein P is phenyl, naphthyl, a 6-membered heteroaryl group containing one or two nitrogen atoms as ring members, or a 10-membered bicyclic heteroaryl group containing one or two nitrogen atoms as ring members, and wherein the phenyl, naphthyl and heteroaryl groups are optionally substituted; R1 is chlorodifluoromethyl or trifluoromethyl; R2 is optionally substituted aryl or optionally substituted heteroaryl; n is 0 or 1; including the process comprising (a-i) reacting a compound of formula II wherein P, R1 and R2 are as defined for the compound of formula I; with nitromethane in the presence a chiral catalyst to give a compound of formula III wherein P, R1 and R2 are as defined for the compound of formula I; and (a-ii) reductively cyclising the compound of formula III to give the compound of formula I.Type: ApplicationFiled: November 19, 2015Publication date: March 17, 2016Applicants: Syngenta Participations AG, Syngenta LimitedInventors: Myriem EL QACEMI, Helmars SMITS, Jerome Yves CASSAYRE, Nicholas Phillip MULHOLLAND, Peter RENOLD, Edouard GODINEAU, Thomas PITTERNA
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Patent number: 9233920Abstract: The present invention provides stereoselective processes for the preparation of compounds of formula (I) wherein P is phenyl, naphthyl, a 6-membered heteroaryl group containing one or two nitrogen atoms as ring members, or a 10-membered bicyclic heteroaryl group containing one or two nitrogen atoms as ring members, and wherein the phenyl, naphthyl and heteroaryl groups are optionally substituted; R1 is chlorodifluoromethyl or trifluoromethyl; R2 is optionally substituted aryl or optionally substituted heteroaryl; n is 0 or 1; including the process comprising (a-i) reacting a compound of formula II wherein P, R1 and R2 are as defined for the compound of formula I; with nitromethane in the presence a chiral catalyst to give a compound of formula III Wherein P, R1 and R2 are as defined for the compound of formula I; and (a-ii) reductively cyclizing the compound of formula III to give the compound of formula I.Type: GrantFiled: June 14, 2011Date of Patent: January 12, 2016Assignees: Syngenta Participations AG, Syngenta LimitedInventors: Myriem El Qacemi, Helmars Smits, Jerome Yves Cassayre, Nicholas Phillip Mulholland, Peter Renold, Edouard Godineau, Thomas Pitterna
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Publication number: 20150376135Abstract: The present invention relates to a process for the preparation of bisdihaloalkyl pyrazoles of formula (V) starting from diketones and acylhalides reacted with a Lewis acid, and a subsequent reaction with a substituted hydrazine.Type: ApplicationFiled: February 7, 2014Publication date: December 31, 2015Applicant: Syngenta Participations AGInventors: Anup JAWALEKAR, Helmars SMITS, Laura QUARANTA, Sitaram PAL, David Anthony JACKSON
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Publication number: 20150291510Abstract: The present invention relates to novel triazole derivatives of formula (I) having insecticidal activity, to processes and intermediates for preparing them, to insecticidal, acaricidal, nematicidal or molluscicidal compositions comprising them and to methods of using them to combat and control insect, acarine, nematode or mollusc pests; wherein R1, R2, G1, G2, Q1 and Q2 are as defined in claim 1; or salts thereof.Type: ApplicationFiled: October 24, 2013Publication date: October 15, 2015Inventors: Ottmar Franz Hueter, Pierre Joseph Marcel Jung, Thomas Pitterna, Helmars Smits, Andre Stoller
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Patent number: 9006456Abstract: The present invention provides processes for the preparation of compounds of formula (I) including processes comprising a. reacting a compound of formula (II) with a nucleophile in the presence of water to give a compound comprising a thietane moiety in which the carbon atom at the 3 position of the thietane moiety is bonded to a nitrogen atom; wherein the nucleophile is selected the group consisting of: N3?, a sulfonamide having two hydrogen atoms bound to the nitrogen atom, a diimide having a hydrogen atom bound to the nitrogen atom or an anion thereof, NH2OH and NH3; and b. when the nucleophile used in step a. is N3? or NH2OH, reacting the compound produced in step a. with a suitable reducing agent to give a compound of formula (I); or when the nucleophile used in step a. is a sulfonamide, reacting the compound produced in step a. with a reagent suitable for cleaving the S—N bond of the sulfonamide group to give a compound of formula (I); or when the nucleophile used in step a.Type: GrantFiled: July 5, 2012Date of Patent: April 14, 2015Assignee: Syngenta Participations AGInventors: Jerome Yves Cassayre, Edouard Godineau, Mohamed Abdelouahab Boussemghoune, Helmars Smits
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Publication number: 20140296527Abstract: The present invention relates to processes for the enantio-selective preparation of spyrrolidine derivatives useful in the manufacture of pesticidally active compounds, as well as to intermediates in the processes. The processes include those comprising (a-i) reacting a compound of formula Ia wherein P is alkyl, aryl or heteroaryl, each optionally substituted, wherein the heteroaryl is connected at P via a ring carbon atom; R1 is chlorodifluoromethyl or trifluoromethyl; R2 is aryl or heteroaryl, each optionally substituted; with a source of cyanide in the presence a chiral catalyst to give a compound of formula IIa wherein P, R1 and R2 are as defined for the compound of formula Ia; and (a-ii) oxidising the compound of formula IIa with a peroxy acid, or peroxide in the presence of an acid to give a compound of formula VI wherein R1 and R2 are as defined for the compound of formula Ia.Type: ApplicationFiled: September 28, 2012Publication date: October 2, 2014Applicant: SYNGENTA PARTICIPATIONS AGInventors: Tomas Smejkal, Helmars Smits, Sebastian Volker Wendeborn, Guillaume Berthon, Jerome Yves Cassayre, Myriem El Qacemi
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Publication number: 20140187788Abstract: The present invention provides processes for the preparation of compounds of formula (I) including processes comprising a. reacting a a compound comprising a thietane moiety in which the carbon atom at the 3 position of the thietane moiety is bonded to a nitrogen atom; wherein the nucleophile is selected the group consisting of: N3?, a sulfonamide having two hydrogen atoms bound to the nitrogen atom, a diimide having a hydrogen atom bound to the nitrogen atom or an anion thereof, NH2OH and NH3; and b. when the nucleophile used in step a. is N3? or NH2OH, reacting the compound produced in step a. with a suitable reducing agent to give a compound of formula (I); or when the nucleophile used in step a. is a sulfonamide, reacting the compound produced in step a. with a reagent suitable for cleaving the S—N bond of the sulfonamide group to give a compound of formula (I); or when the nucleophile used in step a. is a diimide, reacting the compound produced in step a.Type: ApplicationFiled: July 5, 2012Publication date: July 3, 2014Applicant: SYNGENTA PARTICIPATIONS AGInventors: Jerome Yves Cassayre, Edouard Godineau, Mohamed Abdelouahab Boussemghoune, Helmars Smits
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Publication number: 20130237583Abstract: The present invention provides stereoselective processes for the preparation of compounds of formula (I) wherein P is phenyl, naphthyl, a 6-membered heteroaryl group containing one or two nitrogen atoms as ring members, or a 10-membered bicyclic heteroaryl group containing one or two nitrogen atoms as ring members, and wherein the phenyl, naphthyl and heteroaryl groups are optionally substituted; R1 is chlorodifluoromethyl or trifluoromethyl; R2 is optionally substituted aryl or optionally substituted heteroaryl; n is 0 or 1; including the process comprising (a-i) reacting a compound of formula II wherein P, R1 and R2 are as defined for the compound of formula I; with nitromethane in the presence a chiral catalyst to give a compound of formula III Wherein P, R1 and R2 are as defined for the compound of formula I; and (a-ii) reductively cyclising the compound of formula III to give the compound of formula I.Type: ApplicationFiled: June 14, 2011Publication date: September 12, 2013Applicant: SYNGENTA CROP PROTECTION LLCInventors: Myriem El Qacemi, Helmars Smits, Jerome Yves Cassayre, Nicholas Phillip Mulholland, Peter Renold, Edouard Godineau, Thomas Pitterna