Abstract: The present invention provides the novel chlorofluorohydrocarbon 1,1-difluoro-1,4-dichlorobutane, and a process for its preparation by reacting 1,1,1,4-tetrachlorobutane with hydrogen fluoride in the liquid phase. The product has useful solvent properties and is also useful in synthetic chemistry for the introduction of fluorocarbon functionality.
Type:
Grant
Filed:
September 3, 1996
Date of Patent:
December 22, 1998
Assignee:
Zeneca Limited
Inventors:
Alfred Glyn Williams, Martin Charles Bowden, Stephen Martin Brown
Abstract: Aromatic azomethines are produced by continuous reaction of an aniline with a formaldehyde source, with continuous evaporation to remove residual water of reaction. The azomethine product may be further reacted, either continuously or in batch process, with a haloacetylating agent, and, additionally, with an aliphatic alcohol.
Type:
Grant
Filed:
September 19, 1996
Date of Patent:
December 22, 1998
Assignee:
Zeneca Limited
Inventors:
Kambiz Javdani, Louie A. Nady, Ping H. Sih, Gilbert Rodriguez
Abstract: Microcapsules containing a biologically active material which is sensitive to ultraviolet light are prepared which contain an ultraviolet light protectant selected from titanium dioxide, zinc oxide and mixtures thereof, suspended and thoroughly dispersed in a liquid.
Abstract: Phosgenation of carboxylic acids to the corresponding carboxylic acid chlorides in conducted in the presence of a solvent comprising acetonitrile.
Abstract: The invention provides the novel compound 4,4,4-trichlorobutyl methanesufonate, useful as an intermediate in the production of certain agricultural pesticides, and a process for its manufacture.
Type:
Grant
Filed:
December 6, 1996
Date of Patent:
June 2, 1998
Assignee:
Zeneca Limited
Inventors:
Martin Charles Bowden, Trevor Robert Perrior
Abstract: The invention provides novel compounds of formula:CF.sub.3 --CXCl--CH(OH)CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(I)where X represents chloro or bromo and R represents hydrogen or alkyl of up to 4 carbon atoms, processes for preparing them and their use as intermediates in the preparation of insecticidal cyclopropane derivatives. Also provided are novel compounds of formula:BrCH.sub.2 --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(IV)wherein R represents alkyl of up to 4 carbon atoms, useful as intermediates in the preparation of the compounds of formula I.
Abstract: A process for the preparation of 4,4,4-trichlorobutyl acetate comprising reacting allyl acetate with chloroform in the presence of a radical initiator, characterized by the incremental addition of the allyl acetate to the chloroform.
Abstract: The invention provides novel compounds of formula:CF.sub.3 --CXCl--CH(OH)CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(I)where X represents chloro or bromo and R represents hydrogen or alkyl of up to 4 carbon atoms, processes for preparing them and their use as intermediates in the preparation of insecticidal cyclopropane derivatives. Also provided are novel compounds of formula:BrCH.sub.2 --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(IV)wherein R represents alkyl of up to 4 carbon atoms, useful as intermediates in the preparation of the compounds of formula I.
Abstract: There is disclosed a process for the preparation of a lower alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid which comprises the steps of(a) reacting a compound of formula:CF.sub.3 --CXCl--CH(OH)--CH.dbd.C(CH.sub.3).sub.2 (I)wherein X is chloro or bromo, with a tri-lower-alkyl orthoacetate containing up to four carbon atoms in each alkyl groups in the presence of at least a catalytic amount of an acid catalyst at an elevated temperature for a sufficient time to obtain a compound of formula:CF.sub.3 --CXCl--CH.dbd.CH--C(CH.sub.3).sub.2 --CH.sub.2 CO.sub.2 R (III)wherein R is an alkyl group containing up to four carbon atoms, and(b) treating said compound of formula (III) with at least one molar equivalent of a base to obtain said alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid. The products are useful as intermediates for insecticides.
Type:
Grant
Filed:
April 4, 1997
Date of Patent:
March 24, 1998
Assignee:
Zeneca Limited
Inventors:
Martin Charles Bowden, Michael Drysdale Turnbull
Abstract: The invention provides an improved process for the preparation of a lower alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid in which the corresponding lower alkyl ester of a carboxylic acid selected from 6-bromo-6-chloro-3,3-dimethyl-7,7,7-trifluorohept-2-enoic acid and 6,6-dichloro-3,3-dimethyl-7,7,7-trifluorohept-2-enoic acid is treated with an alkali metal lower alkoxylate in the presence of an aromatic hydrocarbon solvent under conditions under which the lower alcohol of the alkoxylate is removed from the reaction mixture by distillation with the aromatic solvent. The products are useful as intermediates in the manufacture of pyrethroid insecticides.
Type:
Grant
Filed:
January 31, 1997
Date of Patent:
March 3, 1998
Assignee:
Zeneca Limited
Inventors:
Martin Charles Bowden, Stephen Martin Brown
Abstract: A rodenticidal bait in the form of agglomerated granules comprising: a cereal base comprising a ground cereal; a rodenticide; and a water-soluble film-forming binder.
Abstract: Noneffervescent pesticidal tablets containing from about 0.1 to about 30 weight percent of a pesticide, from about 0.5 to about 50 weight percent microcrystalline cellulose, from about 5 to about 50 weight percent urea, and from about 0.1 to about 10 weight percent of one or more organic carboxylic acids. The tablets may be packaged in water-soluble film.
Type:
Grant
Filed:
June 21, 1996
Date of Patent:
February 10, 1998
Assignee:
Zeneca Limited
Inventors:
Kang-Chi Lin, Derek A. Stonich, Ralph L. Barnett
Abstract: This invention embodies compositions comprising herbicidally effective compounds corresponding to the formula ##STR1## in which R.sub.1 and R.sub.2 are independently methyl or ethyl,X is H, methyl, chlorine, bromine, fluorine;Y is chlorine, bromine, fluorine; andn is 0, 1 or 2and a non-phytotoxic antidotally effective amount of an antidote therefor selected from the group of amides of haloalkanoic acids, including oxazolidines and thiazolidines, aromatic oxime derivatives, thiazole carboxylic acids and derivatives, substituted phenylpyrimidines, 2-(dichloroacetyl)-2-methyl-1,3-dioxolane and 2-(dichloromethyl)-2-thiazoline.
Abstract: A process whereby N-phosphonomethylglycine (glyphosate) or its salts is manufactured by:1) forming N-phosphonomethylglycinonitrile by reacting aminomethylphosphonic acid, an alkali metal cyanide and formaldehyde in aqueous solution at a pH in the range from 10 to 13 (and preferably from 11 to 11.
Type:
Grant
Filed:
November 13, 1995
Date of Patent:
October 21, 1997
Assignee:
Zeneca Limited
Inventors:
Ian Hodgkinson, John Heathcote Atherton
Abstract: There is disclosed a process for the preparation of a lower alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid which comprises the steps of(a) reacting a compound of formula:CF.sub.3 --CXCl--CH(OH)--CH.dbd.C(CH.sub.3).sub.2 (I)wherein X is chloro or bromo, with a tri-lower-alkyl orthoacetate containing up to four carbon atoms in each alkyl groups in the presence of at least a catalytic amount of an acid catalyst at an elevated temperature for a sufficient time to obtain a compound of formula:CF.sub.3 --CXCl--CH.dbd.CH--C(CH.sub.3).sub.2 --CH.sub.2 CO.sub.2 R(III)wherein R is an alkyl group containing up to four carbon atoms, and(b) treating said compound of formula (III) with at least one molar equivalent of a base to obtain said alkyl ester of 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylic acid. The products are useful as intermediates for insecticides.
Type:
Grant
Filed:
May 26, 1995
Date of Patent:
September 23, 1997
Assignee:
Zeneca Limited
Inventors:
Martin Charles Bowden, Michael Drysdale Turnbull
Abstract: This invention comprises a granular pesticidal composition having improved attrition resistance comprising from about 10 to about 20% by weight of a pesticide, a glycol or polyvinyl alcohol, the remainder comprising montmorillonite or kaolin clay granules.
Abstract: Microspheres containing an agriculturally active material are produced by mixing a liquid phase containing the agriculturally active material and optionally an emulsifying agent and an aqueous phase containing polyvinyl alcohol and adding a material selected from clays, silicas, starch, and starch derivatives, followed by spray drying.
Abstract: A process for the manufacture of an acid salt of an alkyl ester of N-phosphonomethylglycinonitrile is described which comprises reacting methyleneaminoacetonitrile trimer with a trialkylphosphite. The process is carried out under anhydrous conditions and in the presence of an anhydrous acid and an inert solvent in which methyleneaminoacetonitrile trimer is at least partially soluble and the acid salt of the alkyl ester of N-phosphonomethylglycinonitrile product is substantially insoluble. This is followed by recovering the precipitated acid salt of the alkyl ester of N-phosphonomethylglycinonitrile.