Patents by Inventor Harry Tilles

Harry Tilles 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).

  • Patent number: 5266552
    Abstract: Novel herbicides have the formula ##STR1## in which R is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylcarbamoyl, C.sub.1 -C.sub.4 mono- or dialkylamino, phenoxy or nitro;n is 0, 1 or 2;X is oxygen or sulfur;R.sub.1 is C.sub.2 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, 2-trifluoromethylphenyl, 3-trifluoromethoxyphenyl, 4-methoxyphenyl, 4-nitrophenyl, 3,4-dichlorophenyl or benzyl;R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl; andR.sub.3 is C.sub.2 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl, phenyl(C.sub.1 -C.sub.2)-alkyl, 3,4-methylenedioxyphenyl or pyridyl; orR.sub.2 and R.sub.3 taken together with the nitrogen atom form a 4-7 member ring;provided that:a) if X is sulfur, R.sub.2 is not hydrogen;b) if R.sub.2 is hydrogen, R.sub.3 is alkyl, cycloalkyl or phenylalkyl.
    Type: Grant
    Filed: November 12, 1991
    Date of Patent: November 30, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael D. Broadhurst, Harry Tilles
  • Patent number: 4695314
    Abstract: Novel S-benzyl thiolcarbamates are disclosed, having the formula ##STR1## in which R.sup.1 is selected from the group consisting of hydrogen and methoxy,R.sup.2 is selected from the group consisting of methyl, ethyl, and allyl, andR.sup.3 is selected from the group consisting of straight-chain C.sub.3 -C.sub.6 alkyl optionally substituted with one or two methyl groups, and allyl.The compounds are particularly effective in the control of weeds associated with rice crops.
    Type: Grant
    Filed: April 28, 1986
    Date of Patent: September 22, 1987
    Assignee: Stauffer Chemical Company
    Inventors: Lawrence L. Buren, Donald R. James, Barney J. Randolph, Eugene G. Teach, Harry Tilles, Francis H. Walker
  • Patent number: 4341702
    Abstract: Herbicidal active sulfoxide and sulfone compounds and their method of use as described herein. The compounds have the following generic formula: ##STR1## wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and lower haloalkyl; R.sub.1 and R.sub.
    Type: Grant
    Filed: December 24, 1980
    Date of Patent: July 27, 1982
    Assignee: Stauffer Chemical Company
    Inventor: Harry Tilles
  • Patent number: 4299765
    Abstract: Herbicidal active sulfoxide and sulfone compounds and their method of use as described herein. The compounds have the following generic formula: ##STR1## wherein n is 1 or 2; R is selected from the group consisting of lower alkyl and lower haloalkyl; R.sub.1 and R.sub.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: November 10, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Harry Tilles
  • Patent number: 4147715
    Abstract: Thiocarbamates are prepared by a process comprising reacting an aqueous solution of a thiocarbamate salt with an organic halide in the presence of a catalytic amount of a quaternary ammonium salt having the formula(R.sup.4 R.sup.5 R.sup.6 R.sup.7 N).sup.+ Y.sup.-in which R.sup.4 and R.sup.5 are independently selected from the group consisting of C.sub.1 -C.sub.25 alkyl and C.sub.2 -C.sub.25 alkenyl, R.sup.6 and R.sup.7 are independently selected from the group consisting of C.sub.6 -C.sub.25 alkyl and C.sub.6 -C.sub.25 alkenyl, and Y.sup.- is an anion selected from the group consisting of chloride and bromide; and separating the thiocarbamate from the aqueous solution.
    Type: Grant
    Filed: March 23, 1978
    Date of Patent: April 3, 1979
    Assignee: Stauffer Chemical Company
    Inventors: Harry Tilles, Paul E. Hoch
  • Patent number: 4119431
    Abstract: A mixture of cis and trans isomers of S-isopropyl-1-(5-ethyl-2-methylpiperidinecarbothioate) has been found to have improved herbicidal properties in contrast to the trans isomer alone. Preferably the mixture contains at least about 20%, most preferably between about 60 and about 65%, of the cis isomer.The S-isopropyl-1-(5-ethyl-2-methylpiperidinecarbothioate) having a desired amount of cis isomer can be produced by a two-step process comprising hydrogenation of 2-methyl-5-ethyl pyridine using a catalyst comprising rhodium supported on activated carbon to produce 2-methyl-5-ethyl piperidine and reacting the piperidine with isopropyl chlorothiolformate.
    Type: Grant
    Filed: December 27, 1976
    Date of Patent: October 10, 1978
    Assignee: Stauffer Chemical Company
    Inventor: Harry Tilles
  • Patent number: 4101555
    Abstract: A mixture of cis and trans isomers of S-isopropyl-1-(5-ethyl-2-methylpiperidinecarbothioate) has been found to have improved herbicidal properties in contrast to the trans isomer alone. Preferably the mixture contains at least about 20%, most preferably between about 60 and about 65%, of the cis isomer.The S-isopropyl-1-(5-ethyl-2-methylpiperidinecarbothioate) having a desired amount of cis isomer can be produced by a two-step process comprising hydrogenation of 2-methyl-5-ethyl pyridine using a catalyst comprising rhodium supported on activated carbon to produce 2-methyl-5-ethyl piperidine and reacting the piperidine with isopropyl chlorothiolformate.
    Type: Grant
    Filed: December 20, 1976
    Date of Patent: July 18, 1978
    Assignee: Stauffer Chemical Company
    Inventor: Harry Tilles
  • Patent number: 4094895
    Abstract: Novel compounds having the formula ##STR1## in which X is hydrogen, mono- or dihalo or 2-methyl; Y is oxygen or sulfur; R is alkyl, lower alkenyl, chloro-lower alkenyl, carbomethoxymethyl or methyl-thiomethyl; and R.sub.1 is lower alkyl, lower alkenyl or p-chlorobenzyl, provided that if X is 4-chloro, R is other than methyl-thiomethyl. The novel compounds of this type possess aphicidal activity.Also disclosed is a novel process for making O-(substituted)benzyl thiocarbamate intermediates for these compounds.
    Type: Grant
    Filed: August 29, 1977
    Date of Patent: June 13, 1978
    Assignee: Stauffer Chemical Company
    Inventor: Harry Tilles
  • Patent number: 4062971
    Abstract: Novel compounds having the formula ##STR1## in which X is hydrogen, mono- or dihalo or 2-methyl; Y is oxygen or sulfur; R is alkyl, lower alkenyl, chloro-lower alkenyl, carbomethoxymethyl or methyl-thiomethyl; and R.sub.1 is lower alkyl, lower alkenyl or p-chlorobenzyl, provided that if X is 4-chloro, R is other than methyl-thiomethyl. The novel compounds of this type possess aphicidal activityAlso disclosed is a novel process for making O-(substituted)benzyl thiocarbamate intermediates for these compounds.
    Type: Grant
    Filed: August 2, 1976
    Date of Patent: December 13, 1977
    Assignee: Stauffer Chemical Company
    Inventor: Harry Tilles
  • Patent number: 3989684
    Abstract: Intermediate compounds useful for manufacturing herbicidal active sulfoxide and sulfone compounds are described herein. The compounds have the following generic formula: ##EQU1## wherein R is selected from the group consisting of lower alkyl and haloalkyl; R.sub.1 and R.sub.2 taken together can form a heterocyclic ring structure having from 2 to 10 carbon atoms or alkyl substituted heterocyclic ring structure. The heterocyclic ring can be provided with cross-bonding.
    Type: Grant
    Filed: April 9, 1973
    Date of Patent: November 2, 1976
    Assignee: Stauffer Chemical Company
    Inventor: Harry Tilles