May & Baker, Ltd.

Leslie R Hatton

David Alan Roberts

Edgar W Parnell

David William Hawkins

James Gilmour

Susan M Cramp

William George Leeds

Ian George Buntain

Christopher John Pearson

Dennis Warburton

Philip H Smith

Richard G Pennicard

Ian Philip Garland

Neil J Geach

The invention provides a method for the control of arthropod, plant nematode, helminth or protozoan pests using a 2-phenylimidazole derivative of the formula: ##STR1## wherein R.sup.1 represents hydrogen, alkyl (optionally substituted by alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, cyano, carboxy or alkoxycarbonyl), R.sup.2 and R.sup.3, each represents hydrogen, halogen, nitro, carboxy, cyano, alkoxycarbonyl, alkanoyl, or optionally alkyl substituted carbamoyl or sulphamoyl, or amino (optionally substituted by alkyl, alkoxycarbonyl or alkanoyl) or a group R, RO, RS, RSO or RSO.sub.2 in which R represents alkyl (optionally substituted by halogen), and

2-(substituted phenyl)imidazoles and pesticidal compositions comprising

Pesticidal method using 2-phenylimidazole derivatives

A 2-benzoylcyclic-1,3-dione derivative of the formula: ##STR1## wherein X represents methylene, oxygen, sulphur or --NR.sup.4 --, Y represents --C(R.sup.5) (R.sup.6)-- or oxygen, R.sup.1 represents hydrogen or alkyl optionally substituted by halogen or represents cycloalkyl, R.sup.2 represents hydrogen or R.sup.7 or R.sup.1 and R.sup.2 together represent alkylene, R.sup.3 represents halogen, hydroxy, carboxy, nitro, cyano or amino or carbamoyl (which may be substituted by one or two alkyl groups), alkoxycarbonyl, alkanoyl, or alkanoylamino, R, RO, RS, RSO or RSO.sub.2 in which R represents alkyl optionally substituted by halogen, R.sup.4 represents hydrogen or alkyl or alkoxycarbonyl, R.sup.5 represents hydrogen or alkyl or alkoxycarbonyl, R.sup.6 represents hydrogen or alkyl, R.sup.7 represents alkyl which may be substituted by halogen or alkylthio or by a group (R.sup.8).sub.n -phenyl-S-, or represents cycloalkyl or tetrahydrothiapyran-3-yl or represents a group (R.sup.8).sub.n -phenyl- in which R.sup.8 represents a halogen, hydroxy, carboxy, nitro or cyano, or amino or carbamoyl (which may be substituted by one or two alkyl groups), alkoxycarbonyl or alkanoyl or alkanoylamino or R, RO, RS, RSO or RSO.sub.2 in which R represents alkyl which is optionally substituted by halogen, m is zero or 1 to 5 and n is zero or 1 to 5, provided that when X represents methylene, and Y represents --C(R.sup.5) (R.sup.6)--then R.sup.1 and R.sup.2 do nmot simultaneously represent hydrogen or alkyl and salts thereof are useful as herbicides.

Cyclic diones

An N-phenylpyrazol-4-yl ether derivative of the formula: ##STR1## wherein R.sup.1 represents halogen, alkyl or alkoxy unsubstituted or substituted by halogen, alkylthio or alkylsulphinyl substituted by one or more halogen atoms, nitro, cyano, or alkylsulphonyl unsubstituted or substituted by halogen and n is 1 to 5, R.sup.3 represents hydrogen, halogen, cyano, nitro or alkyl group R.sup.2 which may be unsubstituted or substituted by halogen, R.sup.4 represents alkyl, alkenyl or alkynyl which is substituted by halogen, R.sup.5 represents hydrogen or an amino group NR.sup.6 R.sup.7 wherein R.sup.6 and R.sup.7 represent hydrogen, alkyl, formyl or alkanoyl (or R.sup.6 and R.sup.7 together form a 5 or 6 membered cyclic imide) which may be unsubstituted or substituted by halogen, or alkoxycarbonyl unsubstituted or substituted by halogen, or R.sup.5 represents alkoxymethyleneamino unsubstituted or substituted on methylene by alkyl, or represents halogen, or pyrrol-1-yl, pyrazol-1-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-4-yl, piperidino, pyrrolidino, morpholino or N-alkylpiperazino optionally substituted by alkyl or phenyl and pesticidally acceptable acid addition salts thereof, possess arthropodicidal, nematocidal, anthelmintic and anti-protozoal activity.

N-phenylpyrazol-4-yl ether derivatives

An N-phenylpyrazole derivative of the formula: ##STR1## wherein R.sup.1 represents cyano, nitro or halogen;

Derivatives of N-phenylpyrazoles, compositions and use

Compounds of the formula: ##STR1## wherein R represents hydroxymethyl, alkoxymethyl of 2 to 6 carbon atoms, optionally substituted phenoxymethyl, alkanoyloxymethyl of 3 to 10 carbon atoms, optionally substituted benzoyloxymethyl, alkylsulphonyloxymethyl of 2 to 9 carbon atoms, optionally substituted phenylsulphonyloxymethyl, formyl, aminomethyl optionally substituted by 1 or 2 alkyl groups of 1 to 4 carbon atoms, or hydroxyiminomethyl, and acid addition salts thereof, are useful as rodenticides.

Phenylpropargylamine derivatives

Herbicidal compounds of the formula: ##STR1## wherein A represents R.sup.1 R.sup.2 N-- (wherein R.sup.1 represents C.sub.1-8 alkyl or C.sub.2-8 alkenyl or alkynyl unsubstituted or substituted by CN, OH, C.sub.1-6 alkoxy, carboxy, C.sub.2-9 alkoxycarbonyl, aminocarbonyl optionally substituted by C.sub.1-8 alkyl or C.sub.2-8 alkenyl, C.sub.1-8 alkoxyaminocarbonyl, C.sub.1-8 alkanesulphonamidocarbonyl, --C(.dbd.O)Het, where Het represents a nitrogen-containing heterocyclic group, or one or more halogen atoms or R.sup.1 represents C.sub.3-6 cycloalkyl optionally substituted by C.sub.1-4 alkyl and R.sup.2 represents H or R.sup.1, or R.sup.1 represents C.sub.1-4 alkylthio and R.sup.2 represents H, or A represents R.sup.p (R.sup.q)--C.dbd.N-- (wherein R.sup.p represents C.sub.1-4 alkoxy or amino substituted by one or two C.sub.1-4 alkyl groups and R.sup.q represents H or C.sub.1-4 alkyl) or A represents 2-oxo-azetidin-1-yl, 2-oxo-pyrrolidin-1-yl or 2-oxo-piperidin-1-yl optionally substituted by C.sub.1-6 alkyl or A represents open-chain alkenylcarbonylamino and B represents phenyl substituted in the 2- position by F, Cl, Br, NO.sub.2, Me or Et and in the 4- position by F, Cl, Br, C.sub.1-4 (optionally substituted by halogen) or C.sub.2-4 alkenyl and alkynyl and optionally substituted in the 3-, 5- and 6- positions by F, Cl, Br, NO.sub.2, Me or Et, or B represents 2,3-dichlorophenyl, and salts thereof.

Herbicidal 5-amino-4-cyano-1-phenylpyrazoles

New N-phenylpyrazole derivatives of the formula: ##STR1## (wherein R.sup.12 represents a chlorine atom, R.sup.13 represents a hydrogen, fluorine or chlorine atom, R.sup.14 represents a hydrogen or fluorine atom and R.sup.15 represents a hydrogen, fluorine or chlorine atom, with the proviso that when R.sup.14 represents a fluorine atom, R.sup.15 represents a fluorine or chlorine atom, or R.sup.12, R.sup.13 and R.sup.15 each represents a fluorine atom and R.sup.14 represents a hydrogen or fluorine atom) possess useful herbicidal properties.

4-Trifluoromethylphenylhydrazinomethylene-malononitriles

Herbicidal 5-amino-4-cyano-1-phenyl-pyrazoles

N-Phenylpyrazole derivatives of the formula: ##STR1## (wherein each of R.sup.5 and R.sup.6 represents a C.sub.1 -C.sub.4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical, or a fluorine, chlorine or bromine atom, each of R.sup.7, R.sup.8 and R.sup.9 represents a hydrogen atom, a C.sub.1 -C.sub.4 alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R.sup.5, R.sup.7, R.sup.8 and R.sup.9 each represents a hydrogen atom and R.sup.6 represents a trifluoromethoxy or trifluoromethyl radical, and R.sup.10 represents a cyano radical or substituted carbamoyl radical --CONHR.sup.11, wherein R.sup.11 represents a methyl or ethyl radical) have been found to possess useful herbicidal properties. All such N-phenylpyrazole derivatives with the exception of 5-amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole and 5-amino-4-cyano-1-(4-chloro-2-methylphenyl)pyrazole are new compounds. Herbicidal compositions containing such N-phenylpyrazole derivatives are described and also processes for the preparation of the new compounds.

N-Phenylpyrazole derivatives

New acylamino-N-phenylpyrazole derivatives of the formula: ##STR1## [wherein R.sup.1 represents R.sup.8 C(.dbd.O)--(wherein R.sup.8 represents H, C.sub.1-7 alkyl or C.sub.1-4 alkoxy optionally substituted by C.sub.1-4 alkoxy, C.sub.2-5 alkoxycarbonyl or halogen, C.sub.3-4 alkenyloxy, C.sub.3-6 cycloalkyl optionally substituted by CH.sub.3 or C.sub.2 H.sub.5, or phenoxy, R.sup.2 represents H or R.sup.8 C(.dbd.O)--, or R.sup.1 and R.sup.2 together represent --CO--(CR.sup.a R.sup.b).sub.m --CO--, R.sup.3 represents F, Cl, Br, C.sub.1-4 alkyl optionally substituted by halogen, or C.sub.2-4 alkenyl, R.sup.4 represents F, Cl, Br, NO.sub.2, CH.sub.3 or C.sub.2 H.sub.5 and R.sup.5, R.sup.6 and R.sup.7 represent H, F, Cl, Br, NO.sub.2, CH.sub.3 or C.sub.2 H.sub.5, or R.sup.4 and R.sup.5 each represent Cl and R.sup.3, R.sup.6 and R.sup.7 each represent H, R.sup.a and R.sup.b represent H or C.sub.1-4 alkyl, and m is 2 or 3] possess useful herbicidal properties.

5-Acylamino-4-cyano-1-phenylpyrazole derivatives and use as herbicides

The invention provides new imidazole derivatives of the general formula: ##STR1## wherein R.sup.1 represents a methyl or ethyl group, R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each represent a hydrogen or halogen atom or an alkyl or alkoxy group which may optionally be substituted by one or more fluorine atoms, and R.sup.2, R.sup.3 and R.sup.4 do not all represent hydrogen atoms, which possess useful herbicidal properties.

Imidazole derivatives

Pyridazine derivatives of the formula: ##STR1## wherein R.sup.1 represents a fluorine, chlorine, bromine or iodine atom or an alkyl, alkoxy, alkylthio, alkylsulphonyl, nitro, trifluoromethyl, cyano, alkoxycarbonyl, carboxy, aminocarbonyl, amino, monoalkylamino or dialkylamino group, R.sup.2 represents a hydrogen atom or an alkyl group, R.sup.3 represents a hydrogen, fluorine, chlorine or bromine atom or an alkyl, methoxy, ethoxy or hydroxy group, or R.sup.2 and R.sup.3 together represent an oxygen atom or a hydroxyimino group, R.sup.4 represents a hydrogen atom or an alkyl group and n represents zero or an integer from 1 to 5 inclusive, are new compounds useful as herbicides.

Growing community of inventors

Chelmsford, United Kingdom

Leslie R Hatton