Fisons Ltd.

Schering Agrochemicals Limited

Agrevo UK Limited

Fbc Limited

Peter S Gates

John Gillon

David Thomas Saggers

Derek Baldwin

Graham Peter Jones

David Edward Saunders

Carol A Wilson

Richard Rees

Gerhard Johann

Thomas Lawley Hough

Gerhard Tarara

Christoph Harde

Gabriele Kru/ Ger

Herbicidal sulfonamides of the formula: ##STR1## and salts thereof, where: A represents a substituted or unsubstituted benzene ring, or a 5- or 6-membered substituted or unsubstituted heteroaromatic ring; Q is --O--, --S-- or a group --CXX'--; X and X', which may be the same or different, are each hydrogen, halogen, cyano, an optionally-substituted alkyl group, or a group --OR.sup.a, --SR.sup.a, or --COR.sup.b ; or one of X and X' represents hydroxy and the other is as defined above; or X and X' together represent .dbd.O or .dbd.S; R.sup.a is an optionally-substituted alkyl, aryl or acyl group; R.sup.b is an optionally-substituted alkyl or aryl group, or a group --OR.sup.c or --NR.sup.c R.sup.d ; R.sup.c and R.sup.d, which may be the same or different, are each hydrogen, or an optionally-substituted alkyl or aryl group; Y is nitrogen or a group CR.sup.9 ; R.sup.1 is an optionally-substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, benzoheterocyclyl or amino group; R.sup.2 is hydrogen, an optionally-substituted alkyl or carboxylic acyl group, or a group --SO.sub.2 R.sup.1 ; R.sup.3 and R.sup.4, which may be the same or different, are each hydrogen, halo, an optionally substituted alkyl, alkoxy, cycloalkyl or amino group, or an optionally-substituted heterocyclyl group; and R.sup.9 represents hydrogen or an optionally-substituted alkyl group.

Sulfonamide herbicides

Pyrimidine derivatives herbicides

Herbicidal haloacetic acid derivatives of the formula: ##STR1## and salts thereof, where: A is --N.dbd. or --CH.dbd.;

Herbicidal pyrimidinyl or triazinyl haloacetic acid derivatives

Herbicides

The invention provides novel herbicidal sulphonanilides of the formula: ##STR1## where R.sup.1 -R.sup.8 have the meanings given in the specification, and salts thereof, processes for their preparation, and herbicidal compositions containing them.

The invention provides certain herbicidal thiazolotriazole sulphonamides, processes for their preparation, and compositions containing them, the compounds being of the formula: ##STR1## where: R.sup.1 and R.sup.2, which may be the same or different, each represent hydrogen, hydroxy, halo, cyano, substituted or unsubstituted alkyl, alkoxy, alkenyloxy, alkynyloxy, aryl, aralkyl, heteroaryl or carbamoyl, or a group --COR.sup.a or --CO.sub.2 R.sup.a or where R.sup.a is hydrogen or alkyl; or R.sup.1 and R.sup.2 together represent an alkylene chain of 3 or 4 carbon atoms;

Compounds of formula ##STR1## where Az is 1-imidazolyl or 1-(1,2,4-triazolyl); R.sup.1 is aryl or optionally substituted alkyl; R.sup.2 and R.sup.3, which may be the same or different, are hydrogen or alkyl or, together with the carbon to which they are attached, form a 5 to 7 membered ring which may contain one or more oxygen atoms and which may be substituted, or when Az is 1-(1,2,4-triazolyl) can together with the carbon to which they attached form a carbonyl group; R.sup.4 is aryl, substituted alkyl or aryloxy, or when R.sup.2 and R.sup.3 form an oxygen containing ring, can be hydrogen or unsubstituted alkyl; and n is 0, 1 or 2; together with acid addition salts, quaternary ammonium salts and complexes of these compounds with metal salts have fungicidal and plant growth regulant activity.

Fungicidal and plant growth regulant triazole and imidazole sulfide

5-Benzofuranyl esters of the general formula ##STR1## wherein the substituents are as defined in the specification, possess physiological activity, particularly plant physiological activity and may be used as herbicides, plant growth regulants, fungicides, insecticides and anthelmintics.

The invention provides herbicidally-active 2,3-dihydro-5-cyanobenzofurans of the formula: ##STR1## (wherein: R.sup.1 and R.sup.2 together represent .dbd.O or R.sup.1 represents hydrogen and R.sup.2 represents hydrogen, hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, alkylthiocarbonyloxy, halogen, isothiocyanato, amino, alkylamino, dialkylamino, arylamino, acylamino, alkoxycarbonylamino, alkylthiocarbonylamino, N-bonded heterocyclyl, cyano or alkylthio; R.sup.3 and R.sup.4 together represent alkylene or each represent hydrogen or alkyl; and R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, each represent hydrogen, halogen, alkyl, alkoxy, acyl or cyano), processes for their preparation and herbicidal compositions containing them. ,

Herbicidal 5-cyano-2,3-dihydro-benzofuran-2-ones

The invention provides herbicidally-active 2,3-dihydro-5-cyanobenzofurans of the formula: ##STR1## (wherein: R.sup.1 and R.sup.2 together represent .dbd.O or R.sup.1 represents hydrogen and R.sup.2 represents hydrogen, hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, alkylthiocarbonyloxy, halogen, isothiocyanato, amino, alkylamino, dialkylamino, arylamino, acylamino, alkoxycarbonylamino, alkylthiocarbonylamino, N-bonded heterocyclyl, cyano or alkylthio; R.sup.3 and R.sup.4 together represent alkylene or each represent hydrogen or alkyl; and R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, each represent hydrogen, halogen, alkyl, alkoxy, acyl or cyano), processes for their preparation and herbicidal compositions containing them.

5-Cyano-2,3-dihydrobenzofurans useful as herbicides

The invention provides herbicidally-active sulphonates of the formula ##STR1## wherein X represents a group --CHR.sup.3 --OR.sup.4 and Y represents a group --OR.sup.5, or X and Y together represent a group --CHR.sup.3 --O-- or a group --CHR.sup.3 --O--Z--O--, the free oxygen atom of which is attached to the benzene ring; R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each represent hydrogen or C 1 to 6 alkyl, or R.sup.1 and R.sup.2 together or R.sup.2 and R.sup.3 together form a C 3 to 6 alkylene chain; R.sup.4 and R.sup.5, which may be the same or different, each represent hydrogen, C 1 to 6 alkyl, C 2 to 6 alkenyl, C 2 to 6 alkynyl, phenyl, a group --C(.dbd.O)R.sup.10 or a group --SO.sub.2 R.sup.11 ; R.sup.6, R.sup.7 and R.sup.8, which may be the same or different, each represent hydrogen, C 1 to 6 alkyl, halogen, cyano, C 2 to 6 carboxylic acyl, or C 1 to 4 alkoxy; R.sup.9 represents C 1 to 6 alkyl, phenyl or C 7 to 10 phenylalkyl (each of which may be unsubstituted or substituted by one or more chlorine or bromine atoms, C 1 to 4 alkyl groups, C 1 to 4 alkoxy groups or nitro groups), C 5 to 7 cycloalkyl, C 1 to 4 alkylamino, or dialkylamino wherein each alkyl moiety has from 1 to 4 carbon atoms; R.sup.10 represents C 1 to 6 alkyl or alkoxy, C 2 to 6 alkenyl or alkenyloxy, C 2 to 6 alkynyl or alkynyloxy, phenyl, phenoxy, phenylamino, C 1 to 6 alkylamino or dialkylamino wherein each alkyl moiety has from 1 to 6 carbon atoms, each of the groups which R.sup.10 may represent being unsubstituted or substituted by one or more halogen atoms or C 1 to 4 alkoxy groups; R.sup.11 represents C 1 to 6 alkyl, phenyl, C 1 to 6 alkylamino or dialkylamino each of the alkyl moieties thereof having from 1 to 6 carbon atoms, each of the groups which R.sup.11 may represent being unsubstituted or substituted by one or more halogen atoms or C 1 to 4 alkoxy groups; Z represents a group of formula --S(.dbd.O)n, --CR.sup.12 R.sup.13 or --P(.dbd.Q)(OR.sup.14)--; n represents 1 or 2; R.sup.12 and R.sup.13, which may be the same or different, each present hydrogen, C 1 to 6 alkyl or alkoxy, C 2 to 6 alkenyl or alkynyl, phenyl, phenoxy, cyano or (C 1 to 6 alkoxy)carbonyl, or R.sup.12 and R.sup.13 together represent an oxygen atom, a sulphur atom, a C 3 to 6 alkylene chain or a C 1 to 6 alkylimino group or a phenylimino group; and R.sup.14 represents C 1 to 6 alkyl; and Q represents oxygen or sulphur, together with processes for their preparation and herbicidal compositions containing them.

Certain herbicidal sulfonates and sulfamates

Pyrogallol is prepared by (A) reacting a halo compound of formula ##STR1## where X represents Br or I, R.sup.1 represents hydrogen, secondary or tertiary alkyl of up to 10 carbon atoms, carboxy or alkoxycarbonyl of 2-5 carbon atoms and R.sup.2 represents hydrogen or alkyl of 1-4 carbon atoms, with an alkali metal alkoxide of formula ROM where M represents an alkali metal and R represents alkyl of 1-4 carbon atoms, to replace each X by OR, and then (B) dealkylating each OR and each OR.sup.2 where R.sup.2 represents alkyl of 1-4 carbon atoms and removing the R.sup.1 group where this is not hydrogen.

Process for preparing pyrogallol

The invention provides herbicidally-active sulphonates of the formula ##STR1## wherein X represents a group --CHR.sup.3 --OR.sup.4 and Y represents a group --OR.sup.5, or X and Y together represent a group --CHR.sup.3 --O-- or a group --CHR.sup.3 --O--Z--O--, the free oxygen atom of which is attached to the benzene ring; R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each represent hydrogen or C 1 to 6 alkyl, or R.sup.1 and R.sup.2 together or R.sup.2 and R.sup.3 together form a C 3 to 6 alkylene chain; R.sup.4 and R.sup.5, which may be the same or different, each represent hydrogen, C 1 to 6 alkyl, C 2 to 6 alkenyl, C 2 to 6 alkynyl, phenyl, a group --O(.dbd.O)R.sup.10 or a group --SO.sub.2 R.sup.11 ; R.sup.6, R.sup.7 and R.sup.8, which may be the same or different, each represent hydrogen, C 1 to 6 alkyl, halogen, cyano, C 2 to 6 carboxylic acyl, or C 1 to 4 alkoxy; R.sup.9 represents C 1 to 6 alkyl, phenyl or C 7 to 10 phenylalkyl (each of which may be unsubstituted or substituted by one or more chlorine or bromine atoms, C 1 to 4 alkyl groups, C 1 to 4 alkoxy groups or nitro groups), C 5 to 7 cycloalkyl, C 1 to 4 alkylamino, or dialkylamino wherein each alkyl moiety has from 1 to 4 carbon atoms; R.sup.10 represents C 1 to 6 alkyl or alkoxy, C 2 to 6 alkenyl or alkenyloxy, C 2 to 6 alkynyl or alkynyloxy, phenyl, phenoxy, phenylamino, C 1 to alkylamino alylamino or dialkylamino wherein each alkyl moiety has from 1 to 6 carbon atoms, each of the groups which R.sup.10 may represent being unsubstituted or substituted by one or more halogen atoms or C 1 to 4 alkoxy groups; R.sup.11 represents C 1 to 6 alkyl, phenyl, C 1 to 6 alkylamino or dialkylamino each of the alkyl moieties thereof having from 1 to 6 carbon atoms, each of the groups which R.sup.11 may represent being unsubstituted or substituted by one or more halogen atoms or C 1 to 4 alkoxy groups; Z represents a group of formula

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Cambridge, United Kingdom

Peter S Gates