Imperial Chemical Industries Limited

Zeneca Limited

Basf Aktiengesellschaft

David J Milner

David Holland

Dale A Laidler

Ronald W Kenyon

David F Newton

John Crosby

Michael J Robson

Nigel Hughes

Alan T Costello

Peter J Cleare

Roger K Huff

David P Devonald

Mark A Spinney

Gareth Andrew DeBoos

Albert Edward Kaye

Warren Hewertson

Ernest S Cleugh

Stephen John Bentley

Hugh Wilma Reed

Preparation process of benzodifuranone dyes

Benzodifurantriones of Formula (1): ##STR1## in which W is unsubstituted or substituted aryl, a process for their preparation via dioxo intermediates and processes for their conversion into benzodifuranone dyes and compounds of Formula (7): ##STR2## are provided wherein R.sup.3 is --H, --COR.sup.2, --SO.sub.2 R.sup.2 -- which R.sup.2 is alkyl, cycloalkyl, aryl or aralkyl and R.sup.4 is --COOR.sup.2, --CONRR.sup.1 in which R and R.sup.1 each independently is --H, alkyl, cycloalkyl, aryl or aralkyl; --COOH or the alkali metal, alkaline earth metal or ammonium salts thereof; or --COX.sup.2 -- which X.sup.2 is halo.

Benzofuranone and benzodifuranone compounds

Process for preparing polycyclic dyes

A process for obtaining an isomer of a compound of general formula

Isomerisation process

A process for the preparation of a polycyclic dye of Formula (1): ##STR1## by reacting a compound of Formula (2): ##STR2## with a benzofuranone of the Formula (3): ##STR3## wherein: Ring A is unsubstituted or is substituted by from one to three groups;

Preparation of polycyclic dyes

A process for the preparation of a polycyclic dye of the Formula (1): ##STR1## by reacting a ketal ester of the Formula (2): ##STR2## with a benzofuranone of the Formula (3): ##STR3## wherein: Ring A is unsubstituted or is substituted by from one to three groups:

The invention provides compounds of formula: ##STR1## wherein R.sup.1 represents hydrogen or halogen and R.sup.2 represents C.sub.1-8 alkyl or C.sub.1-8 haloalkyl, useful as insecticides and knockdown agents. The invention also provides compositions comprising them, methods of their use in controlling insects, and processes for their preparation.

Insecticidal compounds

Process for the monohalogenation of a benzene compound which has 2 or 3 CH.sub.2 OH substituents to obtain a product wherein one of the CH.sub.2 OH substituents is monohalogenated which comprises reacting an aqueous solution of the compound with hydrochloric or hydrobromic acid in the presence of a water immiscible organic solvent which is inert to the reactants, the partition coefficient of the compound in the aqueous/organic phases being greater, with respect to the aqueous phase, than the partition coefficient of the product. The novel compounds

Selective halogenation of benzene di and tri-methanol compounds

Cyanotetrachlorobenzenes, especially ortho- and para- dicyanotetrachlorobenzenes, are prepared by reacting in a liquid medium at 20.degree.-100.degree. C. a corresponding nitrotetrachlorobenzene with, in solution, an inorganic cyanide. Preferably the liquid medium is a two-phase water/water-immiscible organic solvent system, e.g. water/chloroform, a phase transfer catalyst is present and the inorganic cyanide is an alkali metal or alkaline earth metal cyanide. The compounds are useful chemical intermediates in the synthesis of, for instance, pesticidal compounds.

Process for the preparation of cyanotetrachlorobenzenes

Chiral Schiff bases according to the general formula: ##STR1## and transition metal complexes thereof, wherein C.sup.* is an asymmetric carbon atom, R.sup.1 and R.sup.2, which may be the same or different are alkyl, aralkyl, aryl or alkaryl, R.sup.3 is hydrogen, alkyl, aralkyl, aryl or alkaryl, R.sup.4 and R.sup.5, which may be the same or different, are hydrogen or lower alkyl or, where n is 1, may with the cyclic ring to which CR.sup.4 R.sup.5 is attached form a fused system, J is a chain of 3 or 4 atoms which may all be carbon atoms or may be a mixture of carbon atoms and one or more hetero atoms which may be the same or different, which chain with the group C K forms an aromatic system, K is nitrogen, ##STR2## or --NH--, L, each of which may be the same or different, represents a substituent attached to a carbon atom in the chain J and is hydrogen, alkyl, aralkyl, alkaryl, aryl or a substituent containing a hetero-atom; or two L's together with the cyclic ring to which they are attached form a fused system, n is 0, 1 or 2, m is the number of carbon atoms in the chain J. The transition metal is for example copper (II), chromium (II), manganese (II), iron (II), cobalt (II) nickel (II) or palladium (II). The aforesaid complexes may be used as catalysts in the cyclopropanation of olefins by diazoacetates to form insecticide or insecticide precursors.

Chiral amino-alcohol complexes

Chiral Schiff bases according to the general formula: ##STR1## and chiral transition metal complexes thereof, wherein at least the carbon atom of the monosaccharide to which the iminyl nitrogen atom is attached is asymmetric, and at least one of the carbon atoms adjacent the aforesaid carbon atom bears a hydroxyl group, R.sup.1 and R.sup.6 which may be the same or different, are hydrogen or lower alkyl, R.sup.2 is hydrogen, or lower alkyl or together with R.sup.10 forms a divalent hydrocarbon group, R.sup.3 is hydrogen, a sugar residue, or --CH.sub.2 OR.sup.10 in which R.sup.10 is hydrogen, lower alkyl or together with R.sup.2 forms a divalent hydrocarbon group, R.sup.4 is hydrogen or --CH.sub.2 OR.sup.10 in which R.sup.10 is hydrogen, or a lower alkyl, R.sup.5 is hydrogen, OR.sup.1 or a sugar residue, provided that both R.sup.4 and R.sup.5 are not hydrogen, R.sup.7 and R.sup.8 which may be the same or different, are hydrogen, or lower alkyl, or where p is 1, may with the cyclic ring to which CR.sup.7 R.sup.8 is attached form a fused system, R.sup.9 is hydrogen, alkyl, aralkyl, aryl or alkaryl, J is a chain of 3 or 4 atoms which with the group C A forms an aromatic system, which atoms may be carbon atoms or may be a mixture of carbon and one or more hetero atoms which may be the same or different, A is nitrogen, or ##STR2## or --NH--, L each of which may be the same or different, represents a substituent attached to a carbon atom in the chain J and is hydrogen, an alkyl group, aralkyl group, aryl, alkaryl or a substituent containing a hetero-atom; or two L's together with cyclic group to which they are attached form a fused system, m is 0 or 1, n is 0, 1 or 2, provided that n plus m is 0, 1, 2 or 3, p is 0, 1 or 2 and q is the number of carbon atoms in the chain J. The transistion metal is for example copper (II), chromium (II), manganese (II), iron (II), cobalt (II), nickel (II) or palladium (II). The aforesaid complexes may be used as catalysts in the cyclopropanation of olefins by diazoacetates to form insecticide or insecticide precursors.

Chiral sugar complexes

3-(Halogenovinyl- or propenyl-)-2,2-dimethyl cyclopropane-1-carboxylic acid esters, which are precursors of, or may themselves be, pyrethroid insecticides, are prepared by the reaction of certain halogenopentadienes with an alkyl diazoacetate in the presence of a catalyst which is a transition metal complex of certain chiral Schiff bases, which catalysts tend to increase the yield of preferred cis IR isomer relative to the other possible isomers.

Process for the preparation of cyclopropane carboxylic acid esters

Chiral Schiff bases, and transition metal complexes thereof, of formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same ordifferent, are hydrogen, alkyl, aralkyl, aryl, alkaryl, a substituent containing a hetero atom, or two of R.sup.1, R.sup.2 and R.sup.3 together with the pyridine ring from fused system, R.sup.4 and R.sup.5 which may be the same or different, are hydrogen, lower alkyl, or, where n is 1, may with the pyridine ring to which CR.sup.4 R.sup.5 is attached form a fused system, R.sup.6 is hydrogen, alkyl, aralkyl, aryl or alkaryl, n is 0, 1 or 2 and J and K, which may be the same or different, are groups of the formulae: ##STR2## in which C* is an asymmetric carbon atom, and R.sup.7 and R.sup.8, which may be the same or different, are alkyl, aralkyl, aryl or alkaryl, or ##STR3## in which at least the ring carbon atom to which the iminyl nitrogen atom is attached is asymmetric, at least one of the carbon atoms adjacent the said ring carbon atom bears a hydroxyl group, R.sup.9 and R.sup.14, which may be the same or different, are hydrogen or lower alkyl, R.sup.10 is hydrogen, or lower alkyl, or together with R.sup.15 forms a divalent hydrocarbyl group, R.sup.11 is hydrogen, a sugar residue, or --CH.sub.2 OR.sup.15 in which R.sup.15 is hydrogen, lower alkyl or together with R.sup.10 forms a divalent hydrocarbon group, R.sup.12 is hydrogen or --CH.sub.2 OR.sup.15 in which R.sup.15 is hydrogen, or a lower alkyl, R.sup.13 is hydrogen, OR.sup.1, or a sugar residue, provided that both R.sup.12 and R.sup.13 are not hydrogen, m is 0, 1 or 2, p is 0 or 1 provided that m plus p is 0, 1, 2 or 3. The transition metal is for example copper (II), chromium (II), manganese (II), iron (II), cobalt (II), nickel (II) or palladium (II). The aforesaid complexes may be used as catalysts in the cyclopropanation of olefins by diazoacetates to form insecticide or insecticide precursors.

Chiral compounds

1,4-Dialkylbut-2-ene-1,4-diones are obtained by oxidizing a 2,5-dialkylfuran with an aqueous solution of an inorganic hypochlorite at a pH from 7 to 10.

Process for the preparation of 1,4-dialkylbut-2-ene-1,4-diones

Process for the preparation of 3(2,2-dihalovinyl)-2,2-dimethyl cyclopropane carboxylic acids, especially permethrin acid ethyl ester, by reacting a diazoacetic acid ester with a 1,1-dihalo-4-methyl-1,3-pentadiene in the presence of a catalyst comprising a divalent rhodium salt of a carboxylic acid or borofluoric acid. The products have improved yields and better cis/trans isomer ratios than when the more common catalysts, e.g. copper-bronze, are used.

Growing community of inventors

Manchester, United Kingdom

David J Milner