GB2123420A

GB2123420A - Herbicidal N-phenylpyrazole derivatives

Info

Publication number: GB2123420A
Application number: GB08319006A
Authority: GB
Inventors: Leslie Roy Hatton; Edgar William Parnell; David Alan Roberts
Original assignee: MAY AND BARKER Ltd
Current assignee: MAY AND BARKER Ltd
Priority date: 1982-07-15
Filing date: 1983-07-14
Publication date: 1984-02-01
Also published as: GB2123420B; GB8319006D0

Abstract

N-Phenylpyrazole derivatives of the general formula:- <IMAGE> wherein A represents R<1>R<2>N- (wherein R<1> represents C1-8 alkyl or C2-8 alkenyl or alkynyl unsubstituted or substituted by CN, OH, C1-6 alkoxy, carboxy, C2-9 alkoxycarbonyl, aminocarbonyl optionally substituted by one or two C1-8 alkyl or a C2-8 alkenyl or alkynyl groups, C1-8 alkoxyaminocarbonyl, C1-8 alkanesulphonamidocarbonyl, -C(=O)Het where Het represents a nitrogen- containing heterocyclic group, or one or more halogen atoms or R<1> represents C3-6 cycloalkyl optionally substituted by one or more C1-4 ted alkyl groups and R<2> represents H or R<1>, or R<1> represents C1-4 alkylthio and R<2> represents H, or A represents a group of the general formula:- <IMAGE> (wherein R<p> represents C1-4 alkoxy or amino substituted by one or two C1-4 alkyl groups and R<q> represents H or C1-4 alkyl or A represents a group of the general formula:- <IMAGE> (wherein R<a> to R<f> represents H or C1-6 alkyl and m is 0, 1 or 2) and B represents a group of the general formula:- <IMAGE> (wherein R<g> represents F, Cl, Br, C1-4 alkyl optionally substituted by one or more halogen atoms, e.g. CF3, Or C2-4 alkenyl or alkynyl, Rh represents F, Cl, Br, NO2, methyl or ethyl, and R<j>, R<k> and R<n> each repre- sent H, F, Cl, Br, NO2, methyl or ethyl or R<h> and R<j> each represent Cl and R<g>, R<k> and R<n> each represent H and when appropriate salts with agriculturally-acceptable bases possess herbicidal properties. Compounds of general formula II in which A represents an open-chain alkenylcarbonylamino group, which possess herbicidal properties similar to those of the compounds of general formula II wherein A is as hereinbefore defined, are also described.

Description

SPECIFICATION N-phenylpyrazole derivatives useful as herbicides This invention relates to N-phenylpyrazole derivatives, compositions containing them and their use as herbicides.

In J. Org. Chem. Vol. 23, 191-200 (1958), C.C. Cheng and R.K. Robins have described experiments for the preparation of 6-alkyl-4-hydroxypyrazole-[3,4-d]-pyrimidines as analogues of degradation products of pseudovitamin B12. The authors report that these pyrazole[3,4 d]pyrimidine derivatives did not reveal any significant anti-tumour activity but affected the growth of bacteria. They employed, as starting materials, 1-phenyl-5-acetylamino-4-cyanopyra- zoles of the general formula I herein depicted, wherein R represents phenyl, 2-chlorophenyl, 4chlorophenyl, 4-bromophenyl, 4-nitrophenyl or 4-methylphenyl. The compound of general formula I wherein R represents a phenyl group has also been described by T. Higashino, Y. Iwai and E. Hayashi, Chem. Pharm.Bull, 24 (12), 3120-3134 (1976), as an intermediate in the preparation of 1-phenyl-1 H-pyrazolo[3,4-d]-pyrimidine-5-oxide. Neither of these publications contains any suggestion that compounds of general formula I or any other compound disclosed therein possess or would be expected to possess herbicidal activity.

It has now unexpectedly been found after extensive research and experimentation that certain N-phenylpyrazole derivatives possess valuable herbicidal properties.

The present invention accordingly provides, as herbicides, new N-phenylpyrazole derivatives of the general formula II herein depicted, wherein A represents a group of the general formula Ill herein depicted, wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 8, and preferably from 1 to 4, carbon atoms or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8, and preferably 2 to 4, carbon atoms, alkyl, alkenyl and alkynyl groups within the definition of R1 being unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain aikoxycarbonyl group containing from 2 tQ 9, and preferably from 2 to 7, carbon atoms, an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 8, and preferably from 1 to 4, carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8, and preferably from 2 to 4, carbon atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups, may be the same or different, an alkoxyaminocarbonyl group, wherein the alkoxy moiety contains from 1 to 8, and preferably from 1 to 4, carbon atoms and may be straight- or branched-chain, an alkanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 8, and preferably from 1 to 4, carbon atoms and may be straight- or branched-chain, a -C( = O)Het group wherein Het represents a saturated nitrogen-containing heterocylic group having from 3 to 7 atoms in the ring including up to two additional hetero atoms selected from oxygen, nitrogen and sulphur, and linked to the -C( = 0)- group of the group -C( = O)Het by the nitrogen atom, e.g. morpholino, or one or more halogen, e.g. chlorine. atoms, or R1 represents a cycloalkyl group containing from 3 to 6 carbon atoms unsubstituted or substituted by one or more straight- or branched-chain alkyl groups containing from 1 to 4 carbon atoms, for example a methyl or ethyl group, and R2 represents a hydrogen atom or a group within the definition of R1 as hereinbefore defined, or R1 represents an alkylthio group wherein the alkyl moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain and R2 represents a hydrogen atom, or A represents a group of the general formula IIIA herein depicted, wherein RP represents a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms or an amino group substituted by one or two straight-or branched-chain alkyl groups each containing from 1 to 4 carbon atoms, and, which, when the amino group is substituted by two alkyl groups may be the same or different, and Rq represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, or A represents a group of the general formula IV herein depicted, wherein Ra, Rb, RC, Rd, Re and R', which may be the same or different, each represent a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms and m represents 0, 1 or 2 and B represents a group of the general formula V herein depicted, wherein Rs represents a fluorine, chlorine or bromine atom, a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms unsubstituted or substituted by one or more halogen, e.g. fluorine atoms, for example a trifluoromethyl group, or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 4 carbon atoms, Rh represents a fluorine, chlorine or bromine atom or a nitro, methyl or ethyl group and Ri, Rk and Rn, which may be the same or different, each represent a hydrogen, fluorine, chlorine or bromine atom or a nitro, methyl or ethyl group or Rh and Ri each represent a chlorine atom and R9, Rk, and R" each represent a hydrogen atom and when R1 and/or R2 represent an alkyl, alkenyl or alkynyl group substituted by a carboxy group, salts thereof with agriculturally acceptable bases.

It is to be understood that when R2 is other than a hydrogen atom, groups represented by the symbols R1 and R2 in general formula Ill may be the same or different. It is to be further understood that when m represents 1 or 2, Ra and Rb of the portions of the group of general formula IV depicted in general formulae VI and Vll may be the same or different.

When A represents a group of general formula Ill, R' preferably represents an alkyl group preferably containing 1 to 4 carbon atoms, unsubstituted or substituted as hereinbefore indicated.

When A represents an group of general formula lil wherein R' represents a alkyl group substituted as hereinbefore indicated, R1 preferably represents an ethyl, 1-methylethyl or propyl group substituted as hereinbefore indicated or, preferably, a methyl group substituted as herein before indicated.

Preferably, when A represents a group of general formula Ill, R1 represents a methyl, ethyl, npropyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, iso-propoxycarbonylmethyl, n-butoxycarbonylmethyl, n-pentyloxycarbonyimethyl, n-hexyloxycarbonylmethyl, carboxymethyl, carbamylmethyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, diethylaminocarbonylmethyl, methoxymethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonyl-1 -methy- lethyl, 2-methoxycarbonylethyl, 3-methoxycarbonylpropyl, 2-ethoxycarbonylethyl, 2-di-(n-buty I)aminocarbonyl- 1 -methylethyl, 2-di-(n-propyl)aminocarbonyl-1 -methylethyl, 2-ethoxycarbonylpro- pyl, 2-carboxypropyl, 2-carboxy- 1 -methylethyl, 2-carboxyethyl, methoxyaminocarbonylmethyl, morpholin-4-ylcarbonylmethyl, 2-chloroethyl, or 2-hydroxyethyl group and R2 represents a methyl or n-propyl group or, more especially, a hydrogen atom, or R1 represents an ethylthio, n propylthio, iso-propylthio or n-butylthio group and R2 represents a hydrogen atom.

When A represents a group of general formula IIIA, RP preferably represents a methoxy, ethoxy, n-propoxy or diethylamino group and Rq preferably represents a hydrogen atom or a methyl group, e.g. A represents methoxymethyleneamino, ethoxymethyleneamino, n-propoxymethyleneamino, ethoxyethylideneamino or diethylaminomethyleneamino.

When A represents a group of general formula IV, A preferably represents a 2-oxo-azetidin-1yl, 3-methyl-2-oxo-azetidin-l -yl, 4-methyl-2-oxo-azetidin- 1 -yl, 4-ethyl-2-oxo-azetidin- 1 -yl, 2-oxo-4 n-propyl-azetidin- 1 -yl, 3, 3-dimethyi-2-oxo-azetidin-l -yl, 3,4-dimethyl-2-oxo-azetidin- 1 -yl, 4,4-di methyi-2-oxo-azetidin-l -yl, 4-n-hexyl-2-oxo-azetid in-i -yl, 2-oxo-pyrrolidin- 1 -yl, 3-methyl-2-oxo pyrrolidin- 1 -yl or 5-methyl-2-oxo-pyrrolid in-i -yI group.

Preferably, Rg represents a fluorine, chlorine or bromine atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, e.g. a methyl, ethyl, iso-propyl group or a trifluoromethyl group, Rh represents a fluorine, chlorine or bromine atom or a nitro group, Ri represents a hydrogen, fluorine or chlorine atom, Rk represents a hydrogen or fluorine atom and Rn represents a hydrogen, fluorine, chlorine or bromine atom.

More especially, B represents a 2,6-dichloro-4-trifluoromethylphenyl, 2,4,6-trichlorophenyl, 2chloro-4-methylphenyl, 2,3,5,6-tetrafluoro-4-trifluoromethylphenyl, 2,4-dichlorophenyl, 2-chloro4-iso-propylphenyl, 4-ethyl-2, 3,5, 6-tetrafluorophenyl, 2,3,4, 6-tetrachlorophenyl, 4-chloro 2,3, 5,6-tetrafluorophenyl, 2-nitro-4-trifluoromethylphenyl, 4-bromo-2,3, 5,6-tetraf luorophenyl, 2,6-dibromo-4-trifiuoromethylphenyl, pentafluorophenyl, 2-chloro-4-ethylphenyl, 2,3,4, 6-tet- rafluorophenyl or, preferably, 2,3, 4-trichlorophenyl or 2-chloro-4-trifluoromethylphenyl group.

By the term 'salts with agriculturally acceptable bases' is meant salt the cations of which are known and accepted in the art for the formation of salts of pesticidally active acids for agricultural or horticultural use.

Preferably, the salt are water-soluble. Suitable salts with bases include alkali metal (eg sodium and potassium), alkaline earth metal (eg calcium and magnesium), ammonium and amine (eg diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts. It is to be understood that where reference is made in the present specification to the compounds of general formula II, such reference is intended to include also the salts with agriculturally acceptable bases of compounds of general formula II, where appropriate.

The following compounds of general formula II are of particular interest as herbicides: Compound No.

1 4-Cyano-5-ethylamino-1 -(2,3,4-trichloro phenyl)pyrazole 2 4-Cyano-5-n-propylamino-1-(2,3,4-trichloro phenyl)pyrazole 3 4-Cyano-5-methylamino- -(2, 3,4-trichloro- phenyl)pyrazole 4 4-Cyano-5-(prop-2-enyl)amino-1 -(2,3,4- trichlorophenyl)pyrazole 5 4-Cyano-5-(prop-2-ynyl)amino-l -(2,3,4- trichlorophenyl)pyrazole 6 4-Cyano-5-isopropylamino-l -(2,3,4- trichlorophenyl)pyrazole 7 5-n-Butylamino-4-cyano-1-(2,3,4-trichloro phenyl)pyrazole 8 4-Cyano-5-(2-oxo-pyrrolidin- 1 -yl)- 1 - (2,3,4-trichlorophenyl)pyrazole.

9 4-Cyano-5-(4-ethyl-2-oxo-azetidin 1 -yl)-1-(2, 3,4-trichlorophenyl)pyrazole 10 4-Cyano-5-(3, 3-dimethyl-2-oxo-azetidin- 1 -yl)-1 -(2,3,4-trichlorophenyl)pyrazole 11 4-Cyano-5-(4-methyl-2-oxo-azetidin 1 -yl)-1 -(2, 3,4-trichlorophenyl)pyrazole 1 2 4-Cyano-5-(2-oxo-azetidin-1 -yl)-1 - (2, 3,4-trichlorophenyl)pyrazole 1 3 4-Cyano-1 -(2,6-dichloro-4-trifluoro- methylphenyl)-5-(2-oxo-pyrrolidin-1 -yl) pyrazole 14 .4-Cyano-5-(4-methyl-2-oxo-azetidin 1 -yl)-1 -(2,4,6-trichlorophenyl)pyrazole 15 4-Cyano-1-(2,6-dichloro-4-trifluoro methylphenyl)-5-(4-methyl-2-oxo azetidin-1 -yl)pyrazole 16 1-(2-Chloro-4-methylphenyl)-4-cyano 5-(4-methyl-2-oxo-azetidin- 1 -yl)pyrazole 17 4-Cyano-5-(2-oxo-pyrrolidin-1-yl)-1 (2,3, 5,6-tetrafluoro-4-trifluoromethyl- phenyl)pyrazole 18 4-Cyano-1 -(2,4-dichlorophenyl)-5-(4- methyl-2-oxo-azetid in- 1 -yl)pyrazole 1 9 1 -(2-Chloro-4-isopropylphenyl)-4-cyano 5-(4-methyl-2-oxo-azetid in- 1 -yl)pyrazole 20 1-(2-Chloro-4-trifluoromethylphenyl)-4 cyano-5-(3-methyl-2-oxo-azetidin-1-yl) pyrazole 21 1-(2-Chloro-4-trifluoromethylphenyl)-4 cyano-5-(2-oxo-pyrrolidin-1 -yl)pyrazole 22 4-Cyano-5-( 3-methyl-2-oxo-azetidin- 1 -yI)-1 -(2, 3,4-trichlorophenyl)pyrazole 23 5-iso-Butylamino-4-cyano- 1 -(2,3,4- trichlorophenyl)pyrazole 24 5-sec-Butylamino-4-cyano-1-(2,3,4 trichlorophenyl)pyrazole 25 5-sec-Butylamino-1 -(2-chloro-4-tri fluoromethylphenyl)-4-cyanopyrazole 26 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-iso-propylaminopyrazole 27 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-methylaminopyrazole 28 5-n-Butylamino-1-(2-chloro-4-tri fluoromethylphenyl)-4-cyanopyrazole 29 5-iso-Butylamino-1-(2-chloro-4-tri fluoromethylphenyl)-4-cyanopyrazole 30 1 -(2-Chioro-4-trifluoromethylphenyl)- 4-cyano-5-n-propylaminopyrazole 31 1 -(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-ethylaminopyrazole 32 4-Cyano- 1 -(4-ethyl-2, 3,5, 6-tetra- fluorophenyl)-5-methylaminopyrazole 33 4-Cyano-5-ethylamino-1-(4-ethyl 2,3,5,6-tetrafluorophenyl)pyrazole 34 4-Cyano-1 -(4-ethyl-2,3,5,6-tetra- fluorophenyl)-5-n-propylaminopyrazole 35 4-Cyano-1 -(2,4-dichlorophenyl)-5-n- propylaminopyrazole 36 4-Cyano-1 -(2,4-dichlorophenyl)-5- methylaminopyrazole 37 4-Cyano-1 -(2,4-dichlorophenyl)-5- iso-propylaminopyrazole 38 4-Cyano-1 -(2,4-dichlorophenyl)-5- ethylaminopyrazole 39 4-Cyano-5-di(n-propyl)amino-1 - (2,3,4-trichlorophenyl)pyrazole 40 4-Cyano-5-dimethylamino-1 -(2,3,4 trichlorophenyl)pyrazole 41 4-Cyano-5-ethoxycarbonylmethyl- amino-1 -(2,3,4-trichlorophenyl) pyrazole 42 4-Cyano-5-n-propylamino-1 -(2,3,5,6- tetrafluoro-4-trifluoromethylphenyl) pyrazole 43 5-Carboxymethylamino-4-cyano-1-(2,3,4 trichlorophenyl)pyrazole 44 5-Carboxymethylamino- 1 -(2-chloro-4 trifl uoromethyl phenyl)-4-cyanopyrazole 45 5-Carboxymethylamino-4-cyano-1-(4 ethyl-2,3,5,6-tetrafluorophenyl) pyrazole 46 5-Carboxymethylamino-4-cyano- 1 (2,4,6-trichlorophenyl)pyrazole 47 4-Cyano-5-(2-hydroxyethyl)amino- 1 - (2,3,4-trichlorophenyl)pyrazole 48 5-(2-Chloroethyl)amino-4-cyano-1 - 2, 3,4-trichlorophenyl)pyrazole 49 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-ethoxycarbonylmethylamino pyrazole 50 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-methoxycarbonylmethylamino- pyrazole 51 1 -(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-n-propoxycarbonylmethyl- aminopyrazole 52 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-iso-propoxycarbonylmethyl aminopyrazole 53 5-n-Butoxycarbonylmethylamino-1 -(2- chloro-4-trifluoromethylphenyl)-4 cyanopyrazole 54 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-n-pentyloxycarbonylmethyl aminopyrazole 55 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-n-hexyloxycarbonylmethyl- aminopyrazole 56 1-(2-Chloro-4-trifluoromethylphenyl)- 4-cyano-5-ethylaminocarbonylmethyl aminopyrazole 57 5-Carbamylmethylamino-1 -(2-chloro- 4-trifluoromethylphenyl)-4-cyano pyrazole 58 1 -(2-Chloro-4-trifluoromethylphenyl)- 4-cyano-5-methylaminocarbonylmethyl aminopyrazole 59 1 -(2-Chloro-4-trifluoromethylphenyl)- 4-cyano-5-n-propylaminocarbonylmethyl aminopyrazole 60 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-diethylaminocarbonylmethyl- aminopyrazole 61 1 -(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-n-pentylaminocarbonylmethyl- aminopyrazole 62 1 -(2-chloro-4-trifluoromethylphenyl)- 4-cyano-5-n-hexylaminocarbonylmethyl aminopyrazole 63 1 -(2-Ch loro-4-trifl uoromethylphenyl) 4-cyano-5-n-octylaminocarbonylmethyl aminopyrazole 64 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-(morpholin-4-yl)carbonyl methylaminopyrazole 65 4-Cyano-5-ethylamino- 1 -(2,3,5, 6-tetra- fluoro-4-trifluoromethylphenyl)pyrazole 66 4-Cyano-5-(4,4-di methyl-2-oxo-azetidin 1 -yl)- 1 -(2,3,4-trichlorophenyl)pyrazole 67 4-Cyano-5-(3,4-dimethyl-2-oxo-azetidin 1-yl)-1-(2,3,4-trichlorophenyl)pyrazole 68 4-Cyano-5-(5-methyl-2-oxo-pyrrolidin-1 - yl)-1 -(2,3,4-trichlorophenyl)pyrazole 69 4-Cyano-5-(3-methyl-2-oxo-pyrrolidi n- 1 -yl)- 1 (2,3,4-trichlorophenyl)pyrazole 70 4-Cyano-5-(2-oxo-4-n-propylazetidin-1-yl) 1-(2,3,4-trichlorophenyl)pyrazole 71 4-Cyano-5-(4-n-hexyl-2-oxo-azetidin 1 -yl)-1 -(2,3,4-trichlorophenyl)pyrazole 72 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-(4-methyl-2-oxo-azetid in- 1 -yl)pyrazole 73 4-Cyano-5-(4-methyl-2-oxo-azetidin 1 -yl)- 1 -(2,3,4, 6-tetrachlorophenyl)- pyrazole 74 1-(2-Chloro-4-trifluoromethylphenyl) 4-cyano-5-(4-ethyl-2-oxo-azetidin 1 -yl)pyrazole 75 1 -(2-Chloro-4-methylphenyl)-4-cyano- 5-(2-oxo-pyrrolidin-1 -yl)pyrazole 76 4-Cyano-5-(4-methyi-2-oxo-azetidin 1 -yl)- 1 -(2,3,4,6-tetrafluorophenyl) pyrazole 77 1 -(4-Chloro-2,3,5,6-tetrafluorophenyl)- 4-cyano-5-(4-methyl-2-oxo-azetidin 1 -yl)pyrazole 78 4-Cyano-1 -(2,6-dichloro-4-trifluoro- methylphenyl)-5-(2-oxo-azetidin-1 -yl)- pyrazole 79 1 -(2-Chloro-4-trifluoromethylphenyl)-4 cyano-5-(2-oxo-azetidin- 1 -yl)pyrazole 80 4-Cyano-5-(2-oxo-azetid in- 1 -yl)- 1 (2,3,5,6-tetrafluoro-4-trifluoromethyl phenyl)pyrazole 81 4-Cyano- 1 -(4-ethyl-2, 3,5, 6-tetrafl uoro- phenyl)-5-(2-oxo-azetidin- 1 -yl)pyrazole 82 4-Cyano- 1 -(4-ethyl- 1 '3,5, 6-tetrafluoro- phenyl)-5-(3-methyl-2-oxo-azetidin 1 -yl)pyrazole 83 4-Cyano-1 -(2,6-dichloro-4-trifluoro- methylphenyl)-5-ethylthioaminopyrazole 84 4-Cyano-5-iso-propylthioamino-1 - (2,3,4-trichlorophenyl)pyrazole 85 1 -(2-chloro-4-trifluoromethylphenyl)-4 cyano-5-iso-propylth ioaminopyrazole 86 1-(2-Chloro-4-trifluoromethylphenyl)-4 cyano-5-n-propylthioaminopyrazole 87 5-n-Butylthioamino-1 -(2-chloro-4- trifluoromethylphenyl)-4-cyanopyrazole 88 4-Cyano-5-ethylthioamino-1 -(2,3,4 trichlorophenyl)pyrazole 89 1 -(2-Chloro-4-trifluoromethylphenyl)-4 cyano-5-ethylthioaminopyrazole 90 4-Cyano-5-ethoxymethyleneamino-1 -(2,3,4 trichlorophenyl)pyrazole 91 1 -(2-Chloro-4-trifluoromethyl phenyl)-4- cyano-5-ethoxymethyleneaminopyrazole 92 4-Cyano-5-ethoxymethyleneamino-1 - (4-ethyl-2,3,5,6-tetrafluorophenyl) pyrazole 93 4-Cyano-1 -(2,6-dichloro-4-trifluoro methylphenyl)-5-ethoxymethyleneamino pyrazole 94 4-Cyano-5-ethoxymethyleneamino-1 - (2,3,5,6-tetrafluoro-4-trifluoro- methylphenyl)pyrazole 95 4-Cyano-5-methoxymethyleneamino-1 - (2,3,4-trichlorophenyl)pyrazole 96 4-Cyano-5-(1 -ethoxyethylidene)amino 1 -(2,3,4-trichlorophenyl)pyrazole 97 4-Cyano-5-n-propoxymethyleneamino-1 - (2,3,4-trichlorophenyl)pyrazole 98 4-Cyano-5-(methoxymethyl)amino-1 -(2,3,4 trichlorophenyl)pyrazole.

99 4-Cyano-5-(ethoxymethylene)amino- 1 -(2 nitro-4-trifluoromethylphenyl)pyrazole 100 1 -(4-bromo-2,3,5,6-tetrafluorophenyl)- 4-cyano-5-(ethoxymethylene)amino pyrazole 101 4-Cyano-1-(2,6-dibromo-4-trifluoro methylphenyl)-5-(ethoxymethylene)- aminopyrazole 102 4-Cyano- 1 -(2,6-dichloro-4-trifluoro methylphenyl)-5-methylaminopyrazole 103 4-Cyano-1 -(2,6-dichloro-4-trifluoro methyl phenyl)-5-(diethylamino methylene)aminopyrazole 104 4-Cyano-5-(ethoxymethylene)amino-1 pentafluorophenylpyrazole 105 1 -(2-Chloro-4-ethylphenyl)-4-cyano-5- (ethoxymethylene)aminopyrazole 106 1-(2-chloro-4-ethylphenyl)-4-cyano 5-methylaminopyrazole 107 4-Cyano-1 -(2,6-dichloro-4-trifluoro- methylphenyl)-5-n-propylaminopyrazole 108 4-Cyano-1 -(2,6-dichloro-4-trifluoro- methylphenyl)-5-di(n-propyl)amino pyrazole 109 4-Cyano-5-methoxymethylamino-1 - (pentafluorophenyl)pyrazole 110 4-Cyano-1 -(2,6-dibromo-4-trifluoro methylphenyl)-5-methylaminopyrazole 111 4-Cyano-5-methylamino-1-(pentafluoro- phenyl)pyrazole 112 4-Cyano-5-methylamino-1-(2,3,5,6-tetra fluoro-4-trifluoromethylphenyl)pyrazole 113 4-Cyano-5-methoxycarbonylmethylamino 1-(2,3,5,6-tetrafluoro-4-trifluoromethyl phenyl)pyrazole 1 14 1 -(2-Chloro-4-trifluoromethylphenyl)-4 cyano-5-(2-hydroxyethyl)a minopyrazole 115 1-(2-Chloro-4-trifluoromethylphenyl)-4- cyano-5-n-octyloxycarbonylmethylamino pyrazole 116 l-(2-Chloro-4-trifluoromethylphenyl)-4- cyano-5-iso-propylaminocarbonylmethyl aminopyrazole 117 5-n-Butylaminocarbonylmethylamino-1 (2-chloro-4-trifluoromethylphenyl)-4 cya nopyrazole 118 4-Cyano-1-(2,6-dichloro-4-trifluoro methylphenyl)-5-(2-methoxycarbonylethyl) aminopyrazole 119 4-Cyano-5-(2-ethoxycarbonyl-1-methyl ethyl)amio-1-(2,3,4-trichlorophenyl) pyrazole 120 1-(2-Chloro-4-trifluoromethylphenyl)-4 cyano-5-(2-methoxycarbonylethyl)amino pyrazole 1 21 4-Cyano-5-(3-methoxycarbonylpropyl)amino 1-(2, 3,4-trichlorophenyl)pyrazole 1 22 4-Cyano-5-(2-ethoxycarbonylethyl)amino-l (2, 3, 5,6-tetrafluoro-4-trifluoromethyl- phenyl)pyrazole 123 4-Cyano-5-[2-di-(n-butyl)aminocarbonyl-1 methylethyl]amino- 1 -(2, 3,4-trichlorophenyl) pyrazole 124 4-Cyano-5-[2-di-(n-butyl)aminocaronyl ethyl]amino-1 -(2,6-dichloro-4-trifluoro methylphenyl)pyrazole 125 1-(2-Chloro-4-trifluoromethylphenyl)-4 cyano-5-[2-di-(n-butyl)aminocarbonyl ethyl]aminopyrazole 1 26 4-Cyano-5-[2-di-(n-propyl)aminocarbonyl 1 -methylethyl]amino-1 -(2, 3,4-trichloro- phenyl)pyrazole 1 27 4-Cyano-5-(2-ethoxycarbonylpropyl)amino 1 -(4-ethyl-2,3,5,6-tetrafluorophenyl)- pyrazole 128 5-(2-Carboxypropyl)amino-4-cyano-1-(4 ethyl-2,3,5,6-tetrafluorophenyl)pyrazole 1 29 5-(2-Carboxy-1 -methylethyl)amino-4-cyano- 1 (2,3,4-trichlorophenyl)pyrazole 1 30 5-(2-Carboxyethyl)a mino-4-cyano- 1 -(4- ethyl-2,3,5,6-tetrafluorophenyl)pyrazole 1 31 5-(2-Carboxyethyl)amino-4-cyano- 1 -(2,6- dichloro-4-trifluoromethylpheny)pyrazole 1 32 5-(2-Carboxyethyl)amino- 1 -(2-chloro-4- trifluoromethylphenyl)-4-cyanopyrazole 1 33 1 -(2-Chloro-4-trifl uoromethylphenyl)-4- cyano-5-(methoxyaminocarbonyl methylamino) pyrazole According to a feature of the present invention, there is provided a method for controlling the growth of weeds (i.e. undesired vegetation) at a locus which comprises applying to the locus a herbicidally effective amount of at least one N-phenylpyrazole derivative of general formula II.

For this purpose, the N-phenylpyrazole derivatives are normally used in the form of herbicidal compositions (i.e. in association with compatible diluents or carriers suitable for use in herbicidal compositions), for example as hereinafter described.

The compounds of general formula II show herbicidal activity against dicotyledonous (i.e.

broad-leafed) and monocotyledonous (e.g. grass) weeds by pre- and/or, post-emergence application.

By the term "pre-emergence application" is meant application to the soil in which the weed seeds or seedlings are present before emergence of the weeds above the surface of the soil. By the term 'post-emergence application' is meant application to the aerial or exposed portions of the weeds which have emerged above the surface of the soil.For example, the compounds of general formula II may be used to control the growth of broad-leafed weeds, for example, Aethusa cynapium, Abutilon theophrasti, Amaranthus retroflexus, Amsinckia in term edia, Anagallis arvensis, Anthemis arvensis, Atriplex patula, Bidens pilosa, Brassica nigra, Capsella bursapastoris, Chenopodium album, Chrysanthemum segetum, Cirsium arvense, Datura stramonium, Desmodium tortuosum, Emex australia, Euphorbia helioscopia, Fumaria officinalis, Galeopsis tetrahit, Galium aparine, Geranium dissectu, Ipomea purpurea, Lamium purpureum, Lapsana communis, Matricaria inodora, Monochoria vaginalis, Palaver rhoeas, Physalis longifolia, Plan ta go lanceolata, Polygonum spp., (e.g.Polygonum lapathifolium, Polygonum aviculare, Polygonum convolvulus and Polygonum persicaria), Portulaca oleracea, Raphanus raphanistrum, Rotala indica, Rumex obtusifolius, Saponaria vaccaria, Scan dip pecten-veneris, Senecio vulgaris, Sesbania florida, Sida spinosa, Silene alba, Sinapis arvensis, Solanum nigrum, Sonchus arvensis, Spergula arvensis, Stellaria media, Thlaspi arvense, Tribulus terrestria, Urtica urens, Veronica hederifolia, Veronica persica, Viola arvensis and Xanthium strumarium, and grass weeds, for example, Alopecurus myosuroides, Apera spica-venti, Agrostis stolonifera, Avena fatua, Avena ludoviciana, Brachiaria spp., Bromus sterilis, Bromus tectorum, Cenchrus spp., Cynodon dactylon, Digitaria sanquinalis, Echinochloa crus-galli, Eleusine indica, Setaria viridis and Sorghum halepense and sedges, for example Cyperus esculentus, Cyperus iria and Cyperus rotundus, and Eleocharis acicularis.

The amounts of compounds of general formula II applied vary with the nature of the weeds, the compositions used, the time of application, the cliamtic and edaphic conditions and (when used to control the growth of weeds in crop-growing areas) the nature of the crops. When applied to a crop-growing area, the rate of application should be sufficient to control the growth of weeds without causing substantial permanent damage to the crop. In general, taking these factors into account, application rates between 0.01 kg and 10 kg of active material per hectare give good results. However, it is to be understood that higher or lower application rates may be used, depending upon the particular problem of weed control encountered.

The compounds of general formula II may be used to control selectivity the growth of weeds, for example to control the growth of those species hereinbefore mentioned, by pre- or postemergence application in a directional or non-directional fashion, e.g. by directional or nondirectional spraying, to a locus of weed infestation which is an area used, or to be used, for growing crops, for example cereals, e.g. wheat, barley, oats, maize and rice, soya beans, field and dwarf beans, peas, lucerne, cotton, peanuts, flax, onions, carrots, cabbage, oilseed rape, sunflower, sugar beet, and permanent or sown grassland before or after sowing of the crop or before or after emergence of the crop. For the selective control of weeds at a locus of weed infestation which is an area used, or to be used, for the growing of crops, e.g. the crops hereinbefore mentioned, application rates between 0.01 kg and 4.0 kg, and preferably between 0.01 kg and 2.0 kg, of active material per hectare are particularly suitable. More particularly, the compounds of general formula Il may be used to control selectively the growth of broad leafed weeds, for example to control the growth of those broad leafed species hereinbefore mentioned, by pre- or, more especially, post-emergence application in a non-directional fashion, e.g. by non-directionai spraying, to an area used for growing cereal crops before or after emergence of both the crop and weeds.

For this purpose, i.e. the selective control of broad leafed weeds by pre- or post-emergence application to an area used for growing cereal crops, application rates between 0.01 and 4.0 kg, and preferably between 0.01 kg and 2.0 kg, of active material per hectare are particularly suitable.

The compounds of general formula II may also be used to control the growth of weeds, especially those indicated above, by pre- or post-emergence application in established orchards and other tree-growing areas, for example forests, woods and parks, and plantations e.g. sugar cane, oil palm and rubber plantations. For this purpose they may be applied in a directional or non-directional fashion (e.g. by directional or non-directional spraying) to the weeds or to the soil in which they are expected to appear, before or after planting of the trees or plantations at application rates between 0.25 kg and 10.0 kg, and preferably between 1.0 kg and 4.0 kg, of active material per hectare.

The compounds of general formula II may also be used to control the growth of weeds, especially those indicated above, at loci which are not crop-growing areas but in which the control of weeds is nevertheless desirable. Examples of such- non-crop-growing areas include airfields, industrial sites, railways, roadside verges, the verges of rivers, irrigation and other waterways, scrublands and fallow or uncultivated land, in particular where it is desired to control the growth of weeds in order to reduce fire risks. When used for such purposes in which a total herbicidal effect is frequently desired, the active compounds are normally applied at dosage.

rates higher-than those used in crop-growing areas as hereinbefore described. The precise dosage will depend upon the nature of the vegetation treated and the effect sought. Pre- or post-emergence-application, and preferably pre-emergence application, in a directional or nondirectional fashion (e.g. by directional or non-directional spraying) at application rates between 2.0 kg and 10.0 kg, and preferably between 4.0 and 10.0 kg, of active material per hectare are particularly suitable for this purpose.

When used to control the growth of weeds by pre-emergence application, the compounds of general formula II may be incorporated into the soil in which the weeds are expected to emerge.

It will be appreciated that when the compounds of general formula Il are used to control the growth of weeds by post-emergence application, i.e. by application to the aerial or exposed portions of emerged weeds, the compounds of general formula ll will also normally come into contact with the soil and may also then exercise a pre-emergence control or later-germinating weeds in the soil.- Where especially prolonged weed control is required, the application of the compounds of general formula. ll may be repeated if required.

According to a further feature of the present invention, there are provided compositions suitable for herbicidal use comprising one or more of the N-phenylpyrazole derivatives of general formula II in association with, and preferably homogeneously dispersed in, one or more compatible herbicidally-acceptable diluents or carriers and/or surface-active agents (i.e. diluents or carriers or surface-active agents of the types generally accepted in the art as being suitable for use in herbicidal compositions and which are compatible with compounds of general formula II).

The term "homogeneously dispersed" is used to include compositions in which the compounds of general formula Il are dissolved in the other components. The term "herbicidal compositions' is used in a broad sense to include not only compositions which are ready for use as herbicides but also concentrates which must be diluted before used. Preferably, the compositions contain from 0.05 to 90% by weight of one or more compounds of general formula 11.

The herbicidal compositions may contain both a diluent or carrier and surface-active (e.g.

wetting, dispersing, or emulsifying) agent. Surface-active agents which may be present in herbicidal compositions of the present invention may be of the ionic or non-ionic types, for example sulphoricinoleates, quaternary ammonium derivatives, products based on condensates of ethylene oxide with alkyl and polyaryl phenols, e.g. nonyl- or octyl-phenols, or carboxylic acid esters of anhydrosorbitols which have been rendered soluble by etherification of the free hydroxy groups by condensation with ethylene oxide, alkali and alkaline earth metal salts of sulphuric acid esters and sulphonic acids such as dinonyl- and dioctyl-sodium sulphonosuccinates and alkali and alkaline earth metal salts of high molecular weight sulphonic acid derivatives such as sodium and calcium lignosulphonates and sodium and calcium alkylbenzene sulphonates.

Suitably, the herbicidal compositions according to the present invention may comprise up to 10%, e.g. from 0.05% to 10%, of surface-active agent but, if desired, herbicidal compositions according to the present invention may comprise higher proportions of surface-active agent, for example up to 15% in liquid emulsifiable suspension concentrates and up to 25% in liquid water soluble- concentrates.

Examples of suitable solid diluents or carriers are aluminium silicate, talc, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, adsorbent carbon black and clays such as kaolin and bentonite. The solid compositions (which may take the form of dusts, granules, including dispersible granules, or wettable powders) are preferably prepared by grinding the compounds of general formula II with solid diluents or by impregnating the solid diluents or carriers with solutions of the compounds of general formula II in volatile solvents, evaporating the solvents and, if necessary, grinding the products so as to obtain powders.Granular formulations may be prepared by absorbing the compounds of general formula II (dissolved in suitable solvents, which may, if desired, be volatile) onto the solid diluents or carriers in granular form and, if desired, evaporating the solvents, or by granulating composition in powder form obtained as described above. Solid herbicidal compositions, particularly wettable powders and granules, may contain wetting or dispersing agent (for example of the types described above), which may also, when solid, serve as diluents or carriers.

Liquid compositions according to the invention may take the form of aqueous, organic or aqueous-organic solutions, suspension and emulsions which may incorporate a surface-active agent. Suitable liquid diluents for incorporation in the liquid compositions include water, glycols, tetrahydrofurfuryl alcohol, acetophenone, cyclohexanone, isophorone, toluene, xylene, mineral, animal and.vegetable oils and light aromatic and naphthenic fractions of petroleum (and mixtures of these diluents). Surface-active agents, which may be present in the liquid compositions, may be ionic or non-ionic (for example of the types described above) and may, when liquid, also serve as diluents or carriers.

Wettable powders, dispersible granules and liquid compositions in the form of concentrates may:be diluted with water or other suitable diluents, for example mineral or vegetable oils, particularly in the case of the liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use. When desired, liquid compositions of the compound of general formula Il may be used in the form of self-emulsifying concentrates containing the active substances dissolved-in the emulsifying agents or in solvents containing emulsifying agents compatible with the active substances, the simple addition of water to such concentrates producing compositions ready for use.

Liquid concentrates in which the diluent or carrier is an oil may be used without further dilution using the electrostatic spray technique.

Herbicidal compositions according to the present invention may also contain, if desired, conventional adjuvants such as adhesives, protective colloids, thickeners, penetrating agents, stabilisers, sequestering agents, anti-caking agents, colouring agents and corrosion inhibitors.

These adjuvants may also serve as carriers or diluents.

Preferred herbicidal compositions according to the present invention are aqueous suspension concentrates which comprise from 10 to 70% w/v of one or more compounds of general formula II, from 2 to 10% w/v of surface-active agent, from 0.1 to 5% w/v of thickener and water to 100% by volume; wettable powders which comprise from 10 to 90% w/w of one or more compounds of general formula II, from 2 to 10% w/w of surface-active agent and from 8 to 88% w/w of solid diluent or carrier; liquid water soluble concentrates which comprise from 5 to 50%, e.g. 10 to 30%, w/v of one or more compounds general formula II, from 5 to 25% w/v of surface-active agent and water-miscible solvent, e.g. dimethylformamide, or a mixture of water-miscible solvent and water to 100% by volume; liquid emulsifiable suspension concentrates which comprise from 10 to 70% w/v of one or more compounds of general formula 11, from 5 to 15% w/v of surface-active agents, from 0.1 to 5% w/v of thickener and organic solvent to 100% by volume; granules which comprise from 1 to 90%, e.g. 2 to 10%, w/w of one or more compounds of general formula 11, from 0.5 to 7%, e.g. 0.5 to 2%, w/w of surface-active agent and from 3 to 98.5%, e.g. 88 to 97.5%, w/w of granular carrier and emulsifiable concentrates which comprise 0.05 to 90% w/v, and preferably from 1 to 60% w/v of one or more compounds of general formula 11, from 0.01 to 10% w/v, and preferably from 1 to 10% w/v, of surface-active agent and organic solvent to 100% by volume.

Herbicidal compositions according to the present invention may also comprise the compounds of general formula II in association with, and preferably homogeneously dispersed in, one or more other pesticidally active compounds and, if desired, one or more compatible pesticidally acceptable diluents or carriers, surface-active agents and conventional adjuvants as hereinbefore described.Examples of other pesticidally active compounds which may be included in, or used in conjunction with, the herbicidal compositions of the present invention include herbicides, for example to increase the range of weed species controlled, for example alachlor [2-chlorn-21,61- diethyl-N-(methoxymethyl)-acetanilide], asulam [methyl(4-aminobenzenesulphonyl)-carbamatei, alloxydim Na [sodium salt of 2-( 1 -allyloxy-aminobutylidene)-5, 5-dimethyl-4-methoxycarbonylcy- clohexane-1 3-dione], atrazine [2-chloro-4-ethyiamino-6-isopropylamino-1,3,5-triazine], barban [4-chlorobut-2-ynyl N-(3-chlorophenyl)carbamate], benzoylprop-ethyl [ethyl N-benzoyl-N-(3-,4 dichlcrophenyl-2-aminopropionate], bromoxynil [3,5-dibromo-4-hydroxybenzonitrile], butachlor [N-(butoxymethyl)-2-chloro-2', 6'-d iethylacetanilidej, butylate S-ethyl N, N-diisobutyl(thiocarbamate)], carbetamide [D-N-ethyl-2-(phenylcarbamoxyloxy)propionamide], chlorfenprop-methyl [methyl 2-chloro-3-(4-chlorophenyl)propionatel, chlorpropham (isopropyl N-(3-chlorophenyl)carbamate], chlortciuron [N1-(3-chloro-4-methylphenyl)-N, N-dimethylurea], cyanazine [2-chloro-4-( 1 -cy- ano- 1 -methylethyiamino)-6-ethylamino- 1 , 3, 5-triazine], cycloate [N '-cyclohexyl-N-ethyl-S-ethyl( thiocarbamate)], 2,4-D [2,4-dichlorophenoxyaceticacid], dalapon [2, 2-dichloropropionic acid], 2,4-DB [4-(2,4-dichlorophenoxy)butyric acid], desmedipham [3-(ethoxycarbonylamino)phenyl N phenyl-carbamate], diallate [S-2,3-dichloroallyl-N,N-di-isopropyl(thiocarbamate)], dicamba [3,6dichloro-2-methoxybenzoic acid], dichlorprop C( [(i )-2-(2,4-dichlorophenoxy)propionic acid], difenzoquat [1 , 2-dimethyl-3, 5-diphenyl-pyrazolium salts], dimefuron 4-[2-chloro-4-(3, 3-dimethylurei- do)phenyl]-2-t-butyl-1 , 3,4-oxadiazolin-5-one, dinitramine [N1,N1-diethyl-2, 6-dinitro-4-trifluorome- thyl-mphenylenediaminel, diuron [N'-(3,4-dichlorophenyl)-N, N-dimethylurea], EPTC [S-ethyl N, N-d ipropyl(thiocarbamate)], ethofumesate [2-ethoxy-2, 3-dihydro-3, 3-di methylbenzofuran-5-yl methylsulphonate], flampropisopropyl [isopropyl (i )-2-(N-benzoyl-3-chloro-4-fluoroanilino)pro- pionate], flampropmethyl [methyl ( + )-2-(N-benzoy-3-chloro-4-fluoroanilino)-propionate], fluometuron [N'-(3-trifluoromethylphenyl)-N, N-dimethylurea], ioxynil [4-hydroxy-3,5-di-iodobenzonitri- le], isoproturon (N'-(4-isopropylphenyl)-N, N-dimethylurea], linuron [N-(3,4-dichlorophenyl-N-me- thoxy-N-methylurea], MCPA (4-chloro-2-methylphenoxyacetic acid, MCPB [4-(4-chloro-2-methylphenoxy)butyric acid], mecoprop [(i )-2-(4-chloro-2-methylphenoxy)propionic acid], metamitron [4-amino-3-methyl-6-phenyl- 1,2,4-triazin-5(4H)-one], methabenzthiazuron [N-(benzothiazol-2-yl) N,N'-dimethylurea], metribuzin [4-amino-6-t-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one], molinate [S-ethyl N, N-hexamethylene(th iocarbamate)], oxadiazon [3-(2,4-dichloro-5-isopropoxyphe- nyl)-5-t-bútyl-1,3,4-oxadiazolin-2-one], paraquat [1 , 1 '-dimethyl-4,4'-bipyridyliu m salts], pebulate [S-propyl N-butyl-N-ethyl(thiocarbanate)], phenmedipham [3-(methoxycarbonylamino)phenyl N (3-methyl phenyl)carbamate], prometryne [4,6-bisisopropylamino-2-methylthio- 1,3,5-triazine]; propachlor [2-chloro-N-isopropylacetanilide], propanil [N-(3,4-dichlorophenyl)-propionamide], propham [isopropyl N-phenylcarbamate], pyrazole [5-amino-4-chloro-2-phenylpyridazin-3(2H)- one], simazine [2-chloro-4,6-bisethylamino-1 ,3,5-triazine], TCA (trichloroacetic acid], thiobencarb (8-1 4-chlorobenzyl)-N, N-diethylthiolcarbamate], tri-allate [S-2,3, 3-trichloroallyl N,N-di-iso propyl(thiocarbamate)] and trifluralin [2,6-dinitro-N, N-dipropyl-4-trifluoro-methylaniline]; insecticides, e.g. carbaryl [naphth-1-yl N-methylcarbamate]; synthetic pyrethroids, e.g. permethrin and cypermethrin; and fungicides, e.g. 2,6-dimethyl-4-tridecyl-morpholine, methyl N-( 1 -butyl-carba- moyl-benzimidazol-2-yl)carbamate, 1 , 2-bis-(3-methoxycarbonyl-2-thioureido)benzene, isopropyl 1 -carbamoyl-3-(3, 5-dichlorophenyl)hydantoin and 1 -(4-chloro-phenoxy)-3, 3-dimethyl-1 -(1, 2,4-tri- azol-1-yl)-butan-2-one.Other biologically active materials which may be included in, or used in conjunction with, the herbicidal compositions of the present invention are plant growth regulators, e.g. succinamic acid, (2-chloroethyl)trimethylammonium chloride and 2-chloroethanephosphonic acid; or fertilizers, e.g. containing nitrogen, potassium and phosphorus and trace elements known to be essential to successful plant life, e.g. iron, magnesium, zinc, maganese, cobalt and copper.

Pesticidally active compounds and other biological active materials which may be included in, or used in conjunction with, the herbicidal compositions of the present invention, for example thse hereinbefore mentioned, and which are acids, may, if desired, be utilized in the form of conventional derivatives, for example alkali metal and amine salts and esters.

According to a further feature of the present invention there is provided an article of manufacture comprising at least one of the N-phenylpyrazole derivatives of general formula ll or, as is preferred, a herbicidal composition as hereinbefore described, and preferably a herbicidal concentrate which must be diluted before use, comprising at least one of the N-phenylpyrazole derivative of general formula ll within a container for the aforesaid derivative or derivatives of general formula II, or a said herbicidal composition, and instructions physically associated with the aforesaid container setting out the manner in which the aforesaid derivative or derivatives of general formula ll or herbicidal composition contained therein is to be used to control the growth of weeds.The containers will normally be of the types conventionally used for the storage of chemical substances which are solid at normal ambient temperatures and herbicidal compositions particularly in the form of concentrates, for example cans and drums of metal, which may be internally-lacquered, and plastics materials, bottles of glass and plastics materials and, when the contents of the container is a solid, for example granular, herbicidal compositions, boxes, for example of cardboard, plastics materials and metal, or sacks. The containers will normally be of sufficient capacity to contain amounts of the N-phenylpyrazole derivative or herbicidal compositions sufficient to treat at least one acre of ground to control the growth of weeds therein but will not exceed a size which is convenient for conventional methods of handling. The instructions will be physically associated with the container, for example by being printed directly thereon or on a label or tag affixed thereto. The directions will normally indicate that the contents of the container, after dilution if necessary, are to be applied to control the growth of weeds at rates of application between 0.01 kg and 20 kg of active material per hectare in the manner and for the purposes hereinbefore described.

The following Examples illustrate herbicidal compositions according to the present invention.

EXAMPLE 1 4-cyano-5-ethylamino-1-(2,3,4-trichlorophenyl)pyrazole was formulated as a water soluble concentrate containing 4-cyano-5-ethylamino-1-(2,3,4-trichlorophenyl)pyrazole... ........... . ... .....10% w/v (weight/ volume) Ethylan KEO (nonylphenol/ethylene oxide condensate containing 9-10 moles of ethylene oxide per mole of phenol).. . .....10% w/v Dimethylformamide.. . . .. ....to 100% by volume, by dissolving the Ethylan KEO in a portion of dimethylformamide and then adding the active ingredient with heating and stirring until dissolved. The resulting solution was then made up to 100% by volume by adding the rest of the dimethylformamide.

5 Litres of the above formulation may be dissolved in 200 litres of water and sprayed postemergence onto 1 hectare of an emerged crop of spring-sown wheat to control Amaranthus retroflexus, Setaria viridis, Polygonum lapathifolium, Abutilon theorphrasti and Solanum nigrum.

The 4-cyano-5-ethylamino-1-(2,3,40trichlorophenyl)-pyrazole may, if desired, be replaced in the above water soluble concentrate by any other compound of general formula ll.

EXAMPLE 2 A wettable powder was formed from: 4-cyano-5-ethylamino-1 -(2,3,4-trichlorophenyl)pyrazole.. .. . . ....... .....50% w/w (weight/ weight Ethylan BCP (a nonylphenol/ethylene oxide condensate containing 9 moles of ethylene oxide per mole of phenol) ......... .... 5% w/w Aerosil (silicon dioxide of microfine particle size) . ....... ......... 5% w/w Celite PF (synthetic magnesium silicate carrier).. . . . ............40% w/w by adsorbing the Ethylan BCP onto the Aerosil, mixing with the other ingredients and grinding the mixture in a hammer-mill to give a wettable powder which may be diluted with water and applied at an application rate of 2 kg of wettable powder in 300 litres of spray fluid per hectare to control the growth of Galium aparine, Veronica persica, Viola arvensis, Stellaria media and Galeopsis tetrahit by post-emergence application in an emerged crop of winter wheat.

Similar wettable powders may be prepared as described above by replacing the 4cyano-5- ethylamino-1-(2,3,4-trichlorophenyl)pyrazole by other compounds of general formula ll.

EXAMPLE 3 An aqueous suspension concentrate was formed from:4-cyano-5-ethylamino- 1 -(2,3,4-trichlorophenyl)pyrazole... ................................................... 50% w/v Ethylan BCP................................................. ......... 1.0% w/v Sopropon T36 (sodium salt of polycarboxylic acid) ........................................ 0.2% w/v Ethylene glycol...................................................... 50 w/v Rhodigel 23 (polysaccharide xanthan gum thickener) 0.15% w/v distilled water to 100% by volume by intimately mixing the ingredients and grinding in a ball-mill for 24 hours.The concentrate thus obtained may be dispersed in water and applied at a application rate of 1 kg of aqueous suspension concentrate in 300 litres of spray fluid per hectare to control the growth of Galium aparine, Veronica persica, Viola arvensis, Stellaria media and Galeopsis tetrahit by postemergence application in an emerged crop of winter barley.

Similar aqueous suspension concentrates may be prepared as described above by replacing the 4-cyano-5-ethylamino-1-(2,3,4-trichlorophenyl)pyrazole by other compounds of general formula ll.

EXAMPLE 4 An emulsifiable suspension concentrate was formed from:4-cyano-5-ethylamino-1 -(2,3,4-trichloro phenyl)pyrazole .................... .. ................ 50% w/v Ethylan TU (a nonyl phenol/ethylene oxide condensate containing 10 moles of ethylene oxide per mole of phenol).. . ..............................10% w/v Bentone 38 (an organic derivative of special magnesium montmorillonite thickener)... .........................................................0.5% w/v Aromasol H (an aromatic solvent consisting predominantly of isomeric trimethylbenzenes)... .................................................to 100% by volume by intimately mixing the ingredients and grinding in a ball-mill for 24 hours.The emulsifiable suspension concentrate thus obtained may be diluted with water and applied at an application rate of 1.5 kg of emulsifiable suspension concentrate in 100 litres of spray fluid per hectare t6 control the growth of Setaria viridis, Polygonum convolvulus, and Chenopodium album by post emergence application in an emerged crop of spring-sown wheat.

Similarly emulsifiable suspension concentrates may be prepared as described above by replacing the. 4-cyano-5-ethylamino-1 -(2,3,4-trichlorophenyl)-pyrazole by other compounds of general formula II.

EXAMPLE 5 Granules were formed from: 4cyano-5-ethylamino-1 -(2,3,4-trichloro- phenyl)pyrazole ......... . . 5% w/w Ethylan BCP............................ .... 1% w/w Oleic acid ................. . .. 1% w/w Aromasol H ........ ........ . ... 12% w/w 30/60 Attapulgite granules (sorptive silica clay).. ..... ...81% w/w by mixing the phenylpyrazole, Ethylan BCP, oleic acid and Aromasol H and spraying the mixture onto the Attapulgite granules. The granuls thus obtained may applied at an application rate of 20 kg of granules per hectare to control the growth of Echinochloa crus-galli, Eleocharis acicularis and Monochoria vaginalis by pre-emergence application or application to seedling weeds in a crop of transported paddy rice.

Similar granules may be prepared as described above by replacing the 4-cyano-5-ethylamino1-(2,3,4-trichloro-phenyl)pyrazole by other compounds of general formula II.

EXAMPLE 6 A water soluble concentrate was formed from: 4-cyano-5-ethylamino-1 -(2, 3,4-trichloro- phenyl)pyrazole.. ........... ...... ...10% w/v Ethylan KEO .... . . . ...10% w/v Dimethylformamide... .. to 100% by volume by dissolving the Ethylan KEO in a portion of dimethylformamide and then adding the pyrazole derivative with heating and stirring until dissolved. The resulting solution was then made up to 100% by volume with dimethylformamide by adding the rest of the dimethylformamide. The water soluble concentrate thus obtained may be diluted with water and applied at an application rate of 10 litres of water soluble concentrate in 200 to 2000 litres of spray fluid per hectare to control the growth of Galium aparine, Veronica persica, Viola arvensis and Galeopsis tetrahit by post-emergence application in an emerged crop of winter wheat at the tillering growth stage.

EXAMPLE 7 A wettable powder was formed from:4-cyano-5-ethylamino-1-(2,3,4-trichlorophenyl)pyrazole... ..................... .. . . ...90% w/v Arylan S (sodium dodecyl benzene sulphonate)... ....................... .. 2% w/w Darvan No. 2 (sodium lignosulphate... .. 5% w/w Celite .... . . . . . .. 3% w/w by mixing the ingredients and grinding the mixture in a hammer-mill to give a wettable powder which may be diluted with water and applied at an application rate of 1 kg of wettable powder in 300 litres of spray fluid per hectare to control the growth of Galium aparine, Veronica persica, Viola arvensis and Galeopsis tetrahit by post-emergence application in an emerged crop of winter wheat.

Similar wettable powders may be prepared as described above by replacing the 4-cyano-5ethylamino-1-(2,3,4-trichlorophenyl)pyrazole by other compounds of general formula II.

EXAMPLE 8 A wettable powder containing 50% w/w of 4-cyano-5-ethylamino-1-(2,3,4-trichlorophenyl)py- razole, prepared as hereinbefore described in Example 2, may be diluted with water and applied at an application rate of 0.1 kg of-wettable powder in 300 litres of spray fluid per hectare to control the growth of Abutilon theophrasti and Polygonum convolvulus by post-emergence application at the early seedling growth stage of these weeds in a crop of spring wheat.

EXAMPLE 9 A wettable powder containing 50% w/w of 4-cyano-5-ethylamino-1-(2,3,4-trichlorophenyl)py- razole, prepared as described in Example 2, may be diluted with water and applied at an application rate of 40 kg of wettable powder in 600 litres of spray fluid per hectare to produce a total herbicidal effect on vegetation at a locus which is not a crop-growing area.

EXAMPLE 10 An emulsifiable concentrate was formed from:4-cyano-5-ethylamino-1-(2,3,4-trichlorophenyl)pyrazole... .......................................... .. 20% w/v Soprophor BSU (condensate of tristyrylphenol and ethylene oxide, containing 18 moles of ethylene oxide)............................................ ....3.75 w/v Arylan CA (70% solution of calcium dodecyl benzene sulphonate)... ..... ... ..........................3.75 w/v Isophorone... .. . . . . ... 60% w/v Aromasol H... ........... .......... .........................to 100% by volume, by dissolving the Soprophor BSU and Arylan CA in a portion of the isophorone and then adding the phenylpyrazole, with heating, and stirring until dissolved. The remaining isophorone was then added and the solution was made up to 100% by volume by adding the Aromasol H.The emulsifiable concentrate thus obtained may be diluted with water and applied at an application rate of 1 litre of emulsifiable concentrate in 200 litres of spray fluid per acre (0.4047 hectares) to control the growth of Galium aparine, Stellaria media, Veronica persica, Veronica hederifolia and Viola arvensis by post-emergence application in an emerged crop of winter wheat.

EXAMPLE 11 Water-dispersible granules were formed from: - 4-cyano-5-ethyamino-1 -(2,3,4 trichlorophenyl)pyrazole ................ 90% w/w Arylan S (sodium dodecyl benzene sulphonate)... ............................... ................ 2% w/w Darvan No 2 (sodium lignosulphonate)... . . 5% w/w Celite PF.. .. . . . . . . . . . . .... 3% w/w by mixing the ingredients and grinding in a hammer-mill to give a wettable powder, which was then thoroughly mixed with sufficient water (up to 5% w/w) to give a 'dough'. The 'dough' thus obtained was granulated by passing through an extruder and the granules were dried to remove water.The water-dispersibls granules thus obtained may be diluted with water and applied at an application rate of 1 kg of granules in 300 litres of spray fluid per hectare to control the growth of Galium aparine, Veronica persica, Viola arvensis and Galeopsis tetrahit by post-emergence application in an emerged crop of winter wheat.

Similar water-dispersible granules may be prepared as described above by replacing the 4 cyano-5-ethylamino-1-(2,3-4-trichlorophenyl)pyrazole by other. compounds of general formula l.

EXAMPLE 12 4-cyano-5-(2-oxo-pyrrolidin- 1 -yl)- 1 -(2,3,4trichlorophenyl)pyrazole was formulated as a water soluble concentrate containing 4-cyano-(2-oxo-pyrrolidin-1 -yl)-1 -(2,3,4trichlorophenyl)pyrazole.................... ........ ......10% w/v (weight/ volume) Ethylan KEO (nonylphenol/ethylene oxide condensate containing 9-10 moles of ethylene oxide per mole of phenol)............. . .. 10% w/v Dimethylformamide to 100% by volume, by dissolving the Ethylan KEO in a portion of dimethyl-formamide and then adding the active ingredient with heating and stirring until dissolved. The resulting solution was then made up to 100% by volume by adding the rest of the dimethylformamide.

5 Litres of -the above formulation may be dissolved in 200 litres of water and sprayed postemergence onto 1 hectare of an emerged crop of spring-sown wheat to control Amaranthus retroflexus, Setria viridis, Polygonum lapathifolium, Abutilon theophrasti and Slanum nigrum.

EXAMPLE 13 A wettable powder was formed from:4-cyano-5-(2-oxo-pyrrolidin- 1 -yl)-1 -(2,3,4trichlorophenyl)pyrazole.. . . ....50% w/w (weight/ weight) Ethylan BCP (a nonylphenol/ethylene oxide condensate containing 9 moles of ethylene oxide per mole of phenol)... .. 5% w/w Aerosil (silicon dioxide of microfine particle size)............................... . .. 5% w/w Celite PF (synthetic magnesium silicate carrier).. . . ... AO% w/w by absorbing the Ethylan BCP onto the Aerosil, mixing with the other ingredients and grinding the mixture in a hammer-mill to give a wettable powder which may be diluted with water and applied at an application rate of 2 kg of wettable powder in 300 litres of spray fluid per hectare to control the growth of Galium aparine, Veronica persica, Viola arvensis,Stellaria media and Galeopsis tetrahit by post-emergence application in an emerged crop of wheat.

EXAMPLE 14 An aqueous suspension concentrate was formed from:4-cyano-5-(2-oxo-pyrrolidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole . .. 50% w/v Ethylan BCP ........ .. 1.0% w/v Sopropon T36 (sodium salt of polycarboxylic acid).. . ...0.2% w/v Ethylene glycol................... ......... .. 5% w/v Rhodigel 23 (polysaccharide xanthan gum thickener).. . ...0.15% w/v distilled water to 100% by volume by intimately mixing the ingredients and grinding in a ball-mill for 24 hours. The concentrate thus obtained may be dispersed in water and applied at an application rate of 1 kg of aqueous suspension concentrate in 300 litres of spray fluid per hectare to control the growth of Galium aparine, Veronica persica, Viola arvensis, Stellaria media and Galeopsis tetrahit by postemergence application in an emerged crop of winter barley.

EXAMPLE 15 An emulsifiable suspension concentrate was formed from: 4-cyano-5-(2-oxo-pyrrolidin-1-yl)-1-(2,3,4-trichloro phenyl)pyrazole ................... . ... 50% w/v Ethylan TU (a nonyl phenol/ethylene oxide condensate containing 10 moles of ethylene oxide per mole of phenol).. . ... 10% w/v Bentone 38 (an organic derivative of special magnesium montmorillonite thickener)... ................. . ....0.5% w/v Aromasol H (an aromatic solvent consisting predominantly of isomeric trimethylbenzenes)... . .. to 100% by volume by intimately mixing the ingredients and grinding in a ball-mill for 24 hours.The emulsifiable suspension concentrate thus obtained may be diluted with water and applied at an application rate of 1.5 kg of emulsifiable suspension concentrate in 100 litres of spray fluid per hectare to control the growth of Setaria viridis, Polygonum convolvulus, and Chenopodium album by postemergence application in an emerged crop of spring-sown wheat.

EXAMPLE 16 Granules were formed from:4-cyano-5-(2-oxo-pyrrolidin-1 -yl)- 1 -(2, 3,4-trichloro- phenyl)pyrazole . .. 5% w/w Ethylan BCP.. . ......... . . .. 1% w/w Oleic acid... .... . . ....... ... 1% w/w Aromasol H............................ . . ...12% w/w 30/60 Attapulgite granules (sorptive silica clay).. . . . ......... ....... ...81% w/w by mixing the phenylpyrazole, Ethylan BCP, oleic acid and Aromasol H and spraying the mixture onto the Attapulgite granules. The granules thus obtained may be applied at an application rate of 20 kg of granules per hectare to control the growth of Echinochloa crus-galli, Eleocharis acicularis and Monochoria vaginalis by pre-emergence application or application to seedling weeds in a crop of transplanted paddy rice.

EXAMPLE 17 A water soluble concentrate was formed from:4-cyano-5-(2-oxo-pyrrolidin- 1 -yl)- 1 -(2, 3,4-trichloro- phenyl)pyrazole ............................. ......... ........... 10% w/v Ethylan KEO... .... ............... .......... ...10% w/v Dimethylformamide... .......... ........................to 100% by volume by dissolving the Ethylan KEO in a portion of dimethylformamide and then adding the pyrazole derivative with heating and stirring until dissolved. The resulting solution was then made up to 100% by volume with dimethylformamide by adding the rest of the dimethylformamide.The water soluble concentrate thus obtained may be diluted with water and applied at an application rate of 10 litres of water soluble concentrate in 200 to 2000 litres of spray fluid per hectare to control the growth of Galium aparine, Veronica persica, Viola arvensis and Galeopsis tetrahit by post-emergence application in an emerged crop of winter wheat at the tillering growth stage.

EXAMPLE 18 A wettable powder was formed from:4-cyano-5-(2-oxo-pyrrolidin- 1 -yl)- 1 -(2,3,4trichlorophenyl)pyrazole............ ....... ...90% w/w Arylan S (sodium dodecyl benzene sulphonate)... ...................... .. 2% w/w Darvan No. 2 (sodium lignosulphate)... . . . . 5% w/w Celite .... . . . ....... ...... 3% w/w by mixing the ingredients and grinding the mixture in a hammer-mill to give a wettable powder which may be diluted with water and applied at an application rate of 1 kg of wettable powder in 300 litres of spray fluid per hectare to control the growth of Galium aparine, Veronica persica, Viola arvensis and Galeopsis tetrahit by post-emergence application in an emerged crop of winter wheat.

EXAMPLE 19 A wettable powder containing 50% w/w of 4-cyano-5-(2-oxo-pyrrolidin-1-yl)-1-(2,3,4-trichlo rophenyl)-pyrazole, prepared as hereinbefore described in Example 13, may be diluted with water and applied at an application rate of 0.1 kg of wettable powder in 300 litres of spray fluid per hectare to control the growth of Abutilon theophrasti and Polygonum convolvulus by postemergence application at the early seedling growth stage of these weeds in a crop of spring wheat.

EXAMPLE 20 A wettable powder containing 50% w/w of 4-cyano-5-(2-oxo-pyrrolidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole, prepared as described in Example 13, may be diluted with water and applied at an application rate of 40 kg of wettable powder in 600 litres of spray fluid per hectare to produce a total herbicidal effect on vegetation at a locus which is not a crop-growing area.

EXAMPLE 21 An emulsifiable concentrate was formed from:4-cyano-5-(2-oxo-pyrrolidin-1-yl)-1-(2,3,4trichlorophenyl)pyrazole........................... ............... 20% w/v Soprophor BSU (condensate of tristyrylphenol and ethylene oxide, containing 18 moles of ethylene oxide) 3.75% w/v Arylan CA (70% solution of calcium dodecyl benzene sulphonate)..................................... .................3.75% w/v Isophorone ..... . ........ 60% w/v Aromasol H . to 100% by volume, by dissolving the Soprophor BSU and Arylan CA in a portion of the isophorone and the phenylpyrazole, with heating, and stirring until dissolved. The remaining isophorone was then added and the solution was made up to 100% by volume by adding the Aromasol H.The emu7sifiable concentrate thus obtained may be diluted with water and applied at an application rate of 1 litre of emulsifiable concentrate in 200 litres of spray fluid per acre (0.4047 hectares) to control the growth of Galium aparine, Stellaria Media, Veronica persica, Veronica hederifolia and Viola arvensis by post-emergence application in an emerged crop of winter wheat.

EXAMPLE 22 Water-dispersible granules were formed from:4-cyano-5-(2-oxo-pyrrolidin-1 -yl)-1 -(2,3,4 trichlorophenyl)pyrazole . ... 90% w/w Arylan S (sodium dodecyl benzene sulphonate)............................ .. 2% w/w Darvan No 2 (sodium lignosulphonate) .. 5% w/w Celite .... . .. . 3% w/w by mixing the ingredients and grinding in a hammer-mill to give a wettable powder, which was then thoroughly mixed with sufficient water (up to 5% w/w) to give a 'dough'. The 'dough' thus obtained was granulated by passing through an extruder and the granules were dried to remove water. The water-dispersible granules thus obtained may be diluted with water and applied at an application rate of 1 kg of granules in 300 litres of spray fluid per hectare to control .the growth of Galium aparine, Veronica persica, Viola arvensis and Galeopsis tetrahit by post-emergence application in an emerged crop of winter wheat.

In experiments on herbicidal activity carried out on representative compounds of general formula II, the following results have been obtained: TEST METHOD Weed Control Test (a) General Appropriate quantities of the test compounds, hereinafter identified by the Compound Nos.

hereinbefore indicated, were dissolved in acetone to give solutions equivalent to application rates of 2, 8, 31, 125, 500 and 20009. of test compound per hectare (g/ha). These solutions were applied from a standard laboratory herbicide sprayer using a flat fan jet travelling at 1.6 m.p.h. (2.6 km/hour) and delivering the equivalent of 530 litres of spray fluid per hectare.

(b) Weed Control: Pre-emergence application Weed seeds were sown on the surface of John Innes No. 1 potting compost (7 parts by volume of sterilized loam, 3 parts by volume of peat and 2 parts by volume of fine grit) in 70mm square, 75mm deep plastic pots.The quantities of seed per pot were as follows: Weed species Approximate number seeds/pot (i) Broad leafed weeds Sinapis arvensis 20 Brassica kaber 20 Ipomea purpurea 10 Abutilon theophrasti 10 Chenopodium album 60 (ii) Grass weeds Avena fatua 1 5 Echinóchloa crus-galli 20 (iii) Sedges Cyperus rotundus/esculentus 3 The test compounds were applied to the uncovered seeds as described in (a) above at dose rates equivalent to 2, 8, 31, 125, 500, 20009 of test compound per hectare and the seeds were covered with 25 ml of sharp sand after spraying. A single pot of each weed species was allocated to each treatment, with unsprayed controls and controls sprayed with acetone alone.

After treatment, the pots were kept in the greenhouse and were watered overhead. Visual assessment of weed control activity was made 1 9 to 28 days after spraying. The results were expressed as the effective dose (ED90) in g/ha calculated graphically which gave 90% reduction in growth or kill of the weeds in comparison with plants in the control pots. The results obtained are presented below in Table (c) Weed Control: Post-emergence application Weed species were grown and then transplanted at the seedling stage into John Innes No. 1 potting compost in 70mm square, 75mm deep plastic pots, except for Avena fatua, which was sown directly in the test pot and not transplanted. The plants were then grown in the greenhouse until ready for spraying with the test compounds.The number of plants per pot and the growth of the plant at spraying were as follows: Weed species Number of Growth stages plants/pot at spraying (i) Broad leafed weeds Sinapis arvensis 4 2 leaves Brassica kaber 4 2 leaves Ipomea purpurea 3 1 leaf Abutilon theophrasti 3 2 leaves Chenopodium album 4 2 leaves (ii) Grass weeds Avena fatua 15 1 leaf Echinochloa crus-galli 4 2-3 leaves (iii) Sedges Cyperus rotundus/esculentus 3 2-3 leaves The test compounds were applied to the plants as described in (2) (a) above at dose rates equivalent to 2, 8, 31, 125, 500, 20009 of test compound per hectare. A single pot of each weed species was ailocated to each treatment, with unsprayed controls and controls sprayed with acetone alone. After spraying, the pots were watered overhead, commencing 24 hours after spraying.Assessment of the control of the growth of the weeds was made 19-28 days after spraying by recording the number of plants which has been killed and the reduction in growth.

The results were expressed as the minimum effective dose (ED90) in g/ha calculated graphically which gave 90% reduction in growth or kill of the weeds in comparison with the plants in the control pots. The results obtained are presented below in Table II.

KEY TO WEED SPECIES (a) GRASS WEEDS: Af= Avena fatua Ec = Echinochloa crus-galli (b) BROAD-LEAF WEEDS: At = Abutilon theophrasti Ip = Ipomea purpurea Bk = Brassica kaber Sa = Sinapis arvensis Ca = Chenopodium album (c) SEDGES: CR = Cyperus rotundus or esculentus TABLE I T.C. A.R.

No. PRE-EMERGENCE ED90 (g/ha) g/ha Ca Sa Bk At Ip Af Ec Cr 1 100 30 - 50 125 260 125 > 2000 A 2 < 2 < 2 - 32 > 500 500 450 NR B 3 125 190 - 68 500 500 270 > 500 B 4 < 8 200 - 125 960 1700 500 2000 A 5 < 8 32 - 250 2000 250 250 840 A 6 - < 8 - 16 500 1800 190 NR A 7 - 490 - 50 760 2000 1100 NR A 8 32 24 - 7 110 240 125 32 B 9 2 27 - 20 > 500 490 > 500 NR B 10 > 500 125 - 27 500 NR NR - B 11 8 24 - 19 2000 500 125 > 2000 A 12 500 120 - 125 500 NR NR 500 B 13 - 32 - 500 230 NR 500 NR B 14 < 2 120 - 30 > 500 500 490 NR B 15 < 2 20 - 10 170 125 70 NR B 16 - 1900 - 32 2000 2000 2000 NR A 17 < 8 110 - 125 2000 > 2000 500 > 2000 A 18 < 8 48 - 42 1000 500 500 2000 A 19 2 100 - 125 > 500 500 > 500 NR B 20 - 30 - 8 500 480 480 NR B 21 - 32 - 125 125 NR 500 NR B 22 - 30 - 150 > 500 > 500 > 500 NR B 23 - 490 - 210 1800 1800 1100 1800 A 24 - < 8 - 500 1100 > 2000 500 NR A 25 60 50 - 30 500 > 500 160 NR B 26 8 < 2 - 50 200 200 110 480 B 27 30 30 - 30 70 500 125 > 500 B 28 30 120 - 40 270 > 500 > 500 500 B 29 70 32 - 12 500 500 500 NR B 30 32 30 - 8 190 300 190 500 B 31 30 8 - 7 125 500 125 > 500 B 32 24 30 - 7 105 390 125 500 B 33 24 26 - 2 125 > 500 100 > 500 B 34 2 27 - 8 400 > 500 125 > 500 B 35 125 - 480 280 1100 2000 780 2000 A 36 280 - 410 450 500 > 2000 1100 2000 A 37 125 - 205 360 1650 2000 1000 2000 A 38 72 . - 240 220 500 2000 500 > 2000 A 39 32 ' NR - 2000 2000 2000 > 2000 > 2000 NR A 40 125 500 - 280 280 280 1900 > > 2000 A 41 120 125 - 125 640 2000 800 2000 A 42 32 30 - 190 270 > 500 190 500 B 43 - 120 - 500 900 620 2000 500 A 44 125 110 - 110 280 1100 450 500 A 45 470 - 1350 100 500 > 2000 2000 2000 C 47 67 - 380 110 500 820 980 2000 A 48 96 - 420 125 500 1000 125 > 2000 A 49 90 53 - 108 125 2000 500 2000 A 50 32 90 - 125 360 2000 500 2000 A 51 125 100 - 105 250 2000 500 2000 A 52 125 29 - 32 205 1400 800 1750 A 53 54 - 51 125 500 1100 820 1650 A 54 32 - 195 390 1300 1600 500 2000 A 55 87 - 110 112 500 1150 500 2000 A TABLE I (cont.) T.C. A.R.

No. PRE-EMERGENCE ED90 (g/ha) g/ha Ca Sa Bk At Ip Af Ec Cr 56 26 - 105 1550 110 280 125 2000 A 57 105 - 125 32 70 860 1450 > 2000 A 58 26 - 125 105 26 440 410 > 2000 A 59 32 - 125 66 105 125 360 1100 A 60 26 - 110 70 125 500 500 2000 A 61 26 - 105 105 330 1500 1150 > 2000 A 62 .98 - 380 380 500 > 2000 2000 2000 A 63 @@ 280 - 1450 400 2000 > 2000 > 2000 > 2000 A 64 32 -- 105 52 280 1750 1050 > 2000 A 65 < 8 -- 26 25 100 100 60 1200 A 66 - 125 - 120 NR > 2000 500 NR A 67 410 - 2000 380 > 2000 2000 > 2000 NR A 68 380 125 - 100 1050 NR 1600 NR A 69 " 500 500 - 490 > 2000 NR 1800 2000 A 70 32- 120 - 32 500 500 290 NR A 71 1700 - > 2000 500 2000 NR > 2000 NR A 72 - 6 - 8 500 120 125 NR B 73 - - 30 - 70 > 500 500 500 > 500 B 74 - 8 - 8 500 120 500 NR B 75 32 40 - 2000 2000 NR NR NR A 76 2 84 - 8 490 270 210 - B 77 < 8 120 - 30 30 1100 1000 - A 78 32 - 16 c8 840 840 820 NR A 81 28 - 125 125 500 NR NR NR B 83 - 50 - 32 110 800 450 > 2000 A 84 240 500 - 230 1200 1800 500 2000 A 85 240 220 - 160 270 1200 480 2000 A 86 125 32 - 120 190 2000 190 1800 A 87 - 1900 1200 - 1200 1800 > 2000 1800 NR A 88 - - 120 - 240 800 1800 490 2000 A 89 110 110 - 120 230 1200 290 > 2000 A 90 380 440 - 32 660 1550 440 > 2000 A 90 500 500 - 32 430 > 2000 1800 > 2000 A 92 26. - 100 32 370 1200 500 2000 A 93 -52 - 125 26 88 1500 360 > 2000 A 94 8 -- 90 24 220 340 410 820 A 95 340 105 -- 190 500 1750 1200 > > 2000 A 96 - 440 - 1800 210 > 2000 2000 1650 NR A 97 105 - 500 320 1550 2000 450 > 2000 A TABLEII T.C.A.R No. POST-EMERGENCE ED90 (g/ha) g/ha Ca Sa Bk At Ip Af , Ec Cr 1 28 28 - 25 < 8 2000 500 > 2000 A 2 7 32 - 8 32 500 500 500 B 3 15 1700 - 54 68 NR NR NR B 4 25 60 - 125 32 2000 2000 NR A 5 22 30 - 8 45 2000 > 2000 NR A 6 84 < 8 - < 8 < 8 2000 2000 2000 A 7 8 125 -- 125 500 > > 2000 > > 2000 > > 2000 A 8 8 60 - 2 8 500 270 500 B 9 8 8 - 7 15 125 500 NR B 10 125 125 - < 2 32 500 500 NR B 11 8 < 8 - < 8 < 8 210 700 NR A 12 32 2 - 2 14 500 > 500 NR B 13 125 32 - 500 32 500 500 NR B 14 8 32 - 6 45 500 > 500 NR B 15 8 8 - 2 8 62 125 NR B 16 900 1800 - < 8 900 2000 2000 NR A 17 125 400 -- 125 32 > > 2000 > 2000 > > 2000 A 18 125 < 8 - < 8 42 500 2000 NR A 19 8 20 - 7 7 NR NR NR B 20 8 2 - < 2 7 125 125 NR B 21 125 32 - 125 125 NR NR NR B 22 70 4 -- < 2 8 500 > 500 > > 500 B 23 84 120 - 84 15 2000 2000 NR A 24 8 8 -- 40 28 > > 2000 > 2000 > > 2000 A 25 8 16 - 7 12 > 500 > 500 500 B 26 8 15 - 2 8 > 500 500 500 B 27 10 32 - 19 11 > 500 > 500 500 B 28 7 50 -- 19 12 > > 500 > > 500 > > 500 B 29 32 110 - 32 58 500 > 500 NR B 30 6 40 - 7 15 > 500 500 500 B 31 16 32 -- 19 19 > > 500 > 500 > > 500 B 32 8 18 - 4 32 > 500 390 > 500 B 33 2 14 - < 2 32 > 500 440 > 500 B 34 8 8 - 5 90 > 500 125 > 500 B 35 310 - 1300 8 57 2000 1550 2000 A 36 2000 - 1600 76 125 2000 > 2000 NR A 37 125 -- 125 67 76 > > 2000 > > 2000 > > 2000 A 38 370 - 500 320 105 2000 2000 NR A 39 60 1000 - 600 230 > 2000 2000 NR A 40 30 500 - 30 32 NR NR NR A 41 32 8 - 40 30 2000 500 > 2000 A 42 125 16 - 50 8 500 270 500 B 43 125 32 - 32 500 > 2000 500 > 2000 A 44 < 8 < 8 - 20 105 1750 125 > 2000 A 46 210 -- 1700 28 500 > > 2000 > 2000 > 2000 C 47 115 - 400 8 105 > 2000 2000 > 2000 A 48 90 -- 125 < 8 57 > > 2000 2000 > > 2000 A 49 32 8 - 8 19 > 2000 125 > 2000 A 50 8 8 - < 8 32 2000 125 > 2000 A 51 < 8 8 - 8 60 > 2000 125 2000 A 52 < 8 8 - < 8 32 > 2000 320 > 2000 A 53 64 - 32 < 8 32 > 2000 500 > 2000 A 54 52 - 23 16 72 > 2000 280 > 2000 A 55 56 - 64 32 80 > 2000 500 > 2000 A TABLE II (cont.) T.C. A.R No.POST-EMERGENCE ED90 (g/ha) g/ha Ca Sa Bk At #p Af Ec Cr 56 125 - 125 8 23 2000 840 > 2000 A 57 200 - 350 8 280 > 2000 1300 2000 A 58 125 -- 320 32 32 2000 1400 > 2000 A 59 125 1 125 72 100 980 1200 > 2000 A 60 @ 220 -- 125 32 340 > 2000 1550 2000 A 61 90 - 27 82 340 > 2000 2000 2000 A 62 340 -- 125 96 2000 > > 2000 > > 2000 NR A 63 > 2000 -- 105 1350 2000 > > 2000 > > 2000 > > 2000 A 64 25 -- 115 32 98 > 2000 2000 2000 A 65 32 -- 8 < 8 32 2000 125 2000 A 66 1100 8 -- 84 > > 2000 > 2000 > 2000 NR A 67 1100 -- 240 8 82 > > 2000 > 2000 NR A 68 - 105 210 -- 8 66 NR 2000 NR A 69 .. 300 > 2000 - 1100 > 2000 2000 2000 NR .A 70 6- ' 8 -- 2 8 500 > 500 500 B4 71 -500 -- 125 8 86 2000 2000 NR A 72 . 2 < 2 -- < 2 7 50 210 500 B 73 2 27 -- 8 14 300 26 NR B 74 7 < 2 -- 2 7 70 125 > > 500 B 75 > 2000 NR -- > 2000 > 2000 NR NR NR A 76 125 2 -- 6 68 260 260 NR B 77 < 8 < 8 -- < 8 < 8 640 1600 > 2000 A 78 78 -- < 8 < 8 32 360 500 2000 A 81 58 -- 220 6 34 500 500 NR B 83 @ - 110. 100 -- 50 50 > 2000 500 2000 A 84 230 220 -- 8 120 NR 2000 NR A 85 125 230 -- < 8 70 > 2000 > 2000 2000 A86 180 220 -- 120 32 2000 1800 NR A 87 125 900 -- 300 2000 NR 2000 NR A 88 32 60 -- 125 56 > > 2000 > 2000 > > 2000 A 89 60 60 - 28 24 > 2000 500 2000 A 90 90 < 8 -- < 8 58 > > 2000 370 NR A 91 500 160 - 100 380 2000 > 2000 NR A 92 240 - 500 76 125 > > 2000 2000 > 2000 A 93 500 -- 400 32 84 2000 1350 2000 A 94 125 -- 250 73 32 2000 430 > 2000 A 95 125 500 -- 125 180 > > 2000 1750 NR A 96 125 -- 2000 125 380 2000 2000 NR A 97 350 -- 500 380 125 > > 2000 > 2000 > > 2000 A The following symbols which appear in the above Tables have the following meanings: 'T.C. No.' means = (test) compound number 'A.R. g/ha means = Application Rates (g/ha) applied of the test compound in question.

'A' means = 8 to 2000 g/ha 'B' means = 2 to 500 g/ha 'C' means = 2 to 2000 g/ha means = not tested on that weed species means = much greater than means = greater than means = less than means = no reduction at any dose rate applied.

The results quoted in the columns headed 'CR' refer to application to Cyperus esculentus, except for Compounds Nos. 8 to 24, 72 to 77 and 88, which were applied to Cyperus rotundus.

According to a further feature of the present invention, compounds of general formula ll, wherein A represents a group of general formula Ill and B is as hereinbefore defined may be prepared by the reaction of a compound of the general formula VIII herein depicted, where R1 and R2 are as hereinbefore defined and R3 represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, preferably ethyl, with a compound of the general formula IX herein depicted, wherein B is as hereinbefore defined, or an acid addition salt thereof, e.g.

the hydrochloride.

The reaction of a compound of general formula VII with a compound of general formula IX may be effected in the presence of a suitable inert organic solvent, for example an alkanol containing from 1 to 4 carbon atoms, e.g. ethanol, acetic acid or ethoxyethanol, and at a temperature of from ambient temperature up to the reflux temperature of the reaction mixture, and optionally in the presence of an alkali metal, e.g. sodium or potassium, acetate, carbonate or bicarbonate. When an acid addition salt of the compound of general formula IX is used, the reaction with the compounds of general formula VIII is effected in the presence of an alkali metal, e.g. sodium or potassium, acetate, carbonate or bicarbonate.

According to a further feature of the present invention, compounds of general formula II, wherein A represents a group of general formula Ill wherein R1 is as hereinbefore defined and R2 represents a group identical to the group represented by the symbol R1, and B is as hereinbefore defined, (i.e. compounds of the general formula IIA herein depicted, wherein R1 and B are as hereinbefore defined), or wherein A represents a group of general formula lil, wherein R1 is as hereinbefore defined and R2 represents a hydrogen atom, and B is as hereinbefore defined, (i.e. compounds of the general formula lIB herein depicted wherein R1 and B are as hereinbefore defined), may be prepared by the reaction of a compound of the general formula X herein depicted, wherein B is as hereinbefore defined, or an alkali metal, e.g. sodium or potassium, derivative thereof, with one or two molar proportions of a compound of the general formula Xl herein depicted, wherein R1 is as hereinbefore defined and X represents a chlorine, bromine or iodine atom, in the absence or presence of a suitable inert organic solvent, for example an aromatic hydrocarbon, e.g. benzene or toluene, chloroform, dichloromethane, tetrahydrofuran or dimethylformamide and optionally in the presence of an acid-binding agent, for example pyridine, triethylamine, an alkali metal, e.g. sodium or potassium bicarbonate, and optionally in the presence of a Crown ether (e.g. 1 5-Crown- 5 1,4,7,10,1 3-pentaoxacyclopenta- decane) or 18-Crown-6 (1,4,7,10,13,1 6-hexaoxacyclooctadecane)] at a temperature from O'C up to the reflux temperature of the reaction mixture. The production of compounds of general formulae IIA is favoured by the use of an excess of the compound of general formula Xl. If necessary, a mixture of compounds of general formulae IIA and lIB may be separated by known methods, e.g. crystallisation or chromatography on silica gel.

According to a further feature of the present invention, compounds of general formula II, wherein A represents a group of general formula lil wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms, unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms or one or more halogen, e.g. chlorine, atoms and R2 represents a hydrogen atom, and B is as hereinbefore defined, (i.e. compounds of the general formula IIC herein depicted, wherein R4 represents a straight- or branched-chain alkyl group containing up to 7 carbon atoms, unsubstituted or substituted by a cyano group, a hydroxy group, a straight-or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms, or one or more halogen, e.g. chlorine atoms, R5 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 7 carbon atoms, unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms, or more or more halogen, e.g.

chlorine atoms, R4 and R5 together with the carbon atom to which they are attached representing a straight-or branched-chain alkyl group containing from 1 to 7 carbon atoms, unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branchedchain alkoxycarbonyl group containing from 2 to 9 carbon atoms, or one or more halogen, e.g.

chlorine, atoms, and B as hereinbefore defined), may be prepared by the reduction of the imine double bond of a compound of the general formula XII herein depicted, wherein R4, R5 and B are as hereinbefore defined. Reduction of the imine group of a compound of general formula XII may be effected with an alkali metal, e.g. sodium, boro- or cyanoboro-hydride, in the presence of a suitable inert organic solvent, for example an alkanol containing from 1 to 4 carbon atoms, e.g. methanol or ethanol, or tetrahydrofuran at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

According to a further feature of the present invention, the compounds of general formula II, wherein A represents a group of general formula Ill, wherein R2 represents a hydrogen atom and R1 is are as hereinbefore defined, and B is as hereinbefore defined (i.e. compounds of the general formula lIB herein depicted, wherein R', and B are as hereinbefore defined), may be prepared by the removal of the group R6CO- of a compound of the general formula XIII herein depicted, wherein R6 represents a straight-or branched-chain alkyl or alkoxy group containing from 1 to 4 carbon atoms and R1 and B are as hereinbefore defined.Removal of the group R6CO- may be effected by selective hydrolysis, when R6 represents an alkyl group, under mild alkaline conditions or, when R6 represents an alkoxy group, e.g. t-butoxy, under mild alkaline or acidic conditions, for example by treatment with an alkali metal, e.g. sodium or potassium, hydroxide in water or a suitable inert organic or aqueous-organic solvent, for example a lower alkanol, e.g. methanol, or a mixture of water and lower alkanol, e.g. methanol, or an inorganic acid, e.g. hydrochloric acid, in water or a suitable aqueous-organic solvent, e.g. a mixture of water and a lower alkanol, e.g. methanol, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.As will be readily apparent to those skilled in the art, when R1 in the compound of general formula XIII represents an alkyl, alkenyl or alkynyl group substituted by an alkoxycarbonyl group, removal of the group R6CO- may be accompanied by hydrolysis or, when a lower alkanol is present in the reaction medium, transesterification of the alkoxycarbonyl group to give respectively, a product of general formula IIB wherein R1 is an alkyl, alkenyl or alkynyl group substituted by a carboxy group or wherein R1 is an alkyl, alkenyl or alkynyl group substituted by an alkoxycarbonyl group wherein the alkoxy moiety is the same as that of the lower alkanol present in the reaction medium, according to the reaction conditions used.

According to a further feature of the present invention, the compounds of general formula 11, wherein A represents a group of general formula Ill wherein R' and R2 each represent a methyl group and B is as hereinbefore defined, may be prepared by reaction of a compound of general formula X, wherein B is as hereinbefore defined, with formic acid in the presence of acetic acid.

The reaction may be effected in the absence or presence of a suitable inert organic solvent, for example an aromatic hydrocarbon, e.g. benzene or toluene, at a temperature of from 0 C up to the reflux temperature of the reaction mixture and optionally at elevated pressure.

According to a further feature of the present invention, compounds of general formula II, wherein A represents a group of general formula Ill wherein R1 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms, unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, or one or more halogen, e.g. chlorine, atoms, and R2 represents a hydrogen atom, and B is as hereinbefore defined, (i.e. compounds of the general formula IID herein depicted, wherein R7 represents a straight- or branched-chain alkyl group containing from 1 to 7 carbon atoms, unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, or one or more halogen, e.g. chlorine, atoms, and B is as hereinbefore defined) may be prepared by reduction of the carbonyl group of a compound of the general formula XIV herein depicted, wherein R7 and B are as hereinbefore defined. Reduction of the carbonyl group of a compound of general formula XIV may be effected with an alkali metal, e.g. sodium, boro-ethanedithiolate, in a suitable inert organic solvent, for example a lower alkanol, e.g. methanol or ethanol, or tetrahydrofuran, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

According to a further feature of the present invention, compounds of general formula II wherein A represents a group of general formula Ill, wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms, and R2 is as hereinbefore defined, and B is as hereinbefore defined, may be prepared by transesterification of the alkoxycarbonyl group of a compound falling within the definition given immediately above with an alkanol containing from 1 to 8 carbon atoms e.g. methanol, wherein the alkoxy moiety of the aforesaid alkanol differs from the alkoxy moiety of the aforesaid alkoxycarbonyl substituent in the group R', with, when R2 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by an alkoxycarbonyl containing from 2 to 9 carbon atoms group or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an alkoxycarbonyl group, containing from 2 to 9 carbon atoms, wherein the alkoxy moiety of the alkoxycarbonyl substituent on R2 differs from that of the alkanol used to effect the transesterification, the simultaneous transesterification of the alkoxycarbonyl substituted in R2 to the same alkoxycarbonyl substituent present in R' in the product obtained.Transesterification may be effected with an excess of the alkanol containing from 1 to 8 carbon atoms in the presence of an inorganic acid, e.g. hydrochloric acid, and optionally in the presence of water, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

According to a further feature of the present invention, compounds of general formula ll, wherein A represents a group of general formula Ill, wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms, or alkenyl or alkynyl group containing from 2 to 8 carbon atoms, substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms and R is as hereinbefore defined, and B is as hereinbefore defined, may be prepared by the esterification of the carboxy group(s) of a compound of general formula 11, wherein A represents a group of general formula Ill, wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by a carboxy group or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by a carboxy group and R2 is as hereinbefore defined, and B is as hereinbefore defined, with an alkanol containing from 1 to 8 carbon atoms, with, when R2 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by a carboxy group or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by a carboxy group, simultaneous esterification of the carboxy group substituent in R2.Esterification may be effected with the alkanol containing from 1 to 8 carbon atoms in the presence of an esterifying agent, e.g. sulphuric acid, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

According to a further feature of the present invention, compounds of general formula ll, wherein A represents a group of general formula Ill, wherein R' represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms or alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms, or substituted by an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups each containing from 1 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups, may be the same or different, or substituted by an alkoxyamino-carbonyl group wherein the alkoxy moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain or substituted by an alkanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branchedchain, or substituted by a -COHet group, wherein Het is as hereinbefore defined, R2 represents a hydrogen atom, and B is as hereinbefore defined, (i.e. compounds of the general formula lIE herein depicted, wherein B is as hereinbefore defined, R' represents a straight- or branchedchain alkylene group containing from 1 to 8 carbon atoms or alkenylene or alkynylene group containing from 2 to 8 carbon atoms and T represents a straight- or branched-chain alkoxy group containing from 1 to 8 carbon atoms, an amino group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups each containing from 1 to 8 carbon atoms and which, when the amino group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups may be the same or different, an alkoxyamino group wherein the alkoxy moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, an alkanesulphonamido group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, or a -Het group, wherein Het is as hereinbefore defined), may be prepared by the reaction of a compound of the general formula XV herein depicted, wherein Rr and B are as hereinbefore defined, with a compound of the general formula XVI herein depicted wherein R8 represents a straight- or branched-chain alkoxy group containing from 1 to 8 carbon atoms, an amino group unsubstituted or substituted by one or two straightor branched-chain alkyl groups containing from 1 to 8 carbon atoms and which, when the amino group is substituted by two alkyl groups, may be the same or different, or substituted by one or two, straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8 carbon atoms, and which, when the amino group is substituted by two alkenyl or alkynyl groups, may be the same or different, an alkoxyamino group wherein the alkoxy moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, an alkanesulphonamido group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight-or branched-chain, or a Het group, wherein Het is as hereinbefore defined, or, when R8 represents an alkanesulphonamido group, an alkali metal, e.g. sodium, salt of an alkanesulphonamide represented by general formula XVI. The reaction may be effected, when R8 represents an alkoxy group, in the presence of an excess of the alkanol represented by general formula XVI, or, when R8 represents an amino group unsubstituted or substituted by one or two alkyl, alkenyl or alkynyl groups, an alkoxyamino group, an alkanesulphonamido group or a Het group, in the presence of a suitable inert organic solvent, for example a ketone, e.g. methylethylketone, dimethylformamide or toluene, in the presence, when R8 represents an alkoxy group or an alkanesulphonamido group, of a base, for example an alkali metal, e.g. potassium, carbonate, or, when R8 represents an amino group unsubstituted or substituted or a Het group or an alkoxyamino group, in the presence of an alkali metal, e.g. potassium, carbonate, or an excess of ammonia, mono- or dialkyl-, alkenyl- or alkynyl- amine, alkoxyamine or the heterocyclic compound represented by general formula XVI, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

Compounds of general formula XV may be prepared by the reaction of a compound of general formula li wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by a carboxy group or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by a carboxy group, with thionyl chloride or phosphorous oxychloride, optionally in the presence of an inert organic solvent, e.g., toluene, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture. If desired, compounds of general formula XV may be prepared in situ and reacted with compounds of general formula XVI without previous isolation.A convenient method for preparing compounds of general formula II, wherein A represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms or alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an aminocarbonyl group substituted by one or two alkyl groups each containing from 1 to 8 carbon atoms, R2 represents a hydrogen atoms, and B is as hereinbefore defined, comprises reacting a compound of general formula ll wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by a carboxy group or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by a carboxy group, with phosphorus oxychloride.and the appropriate mono- or dialkylamine in the presence of potassium carbonate at a.temperature of from laboratory temperature up to the reflux temperature of the reaction medium.

The compounds of general formula XV may also be prepared by treating a compound of general formula ll wherein A represents a group of general formula IV, wherein R", Rb, RC, Rd, Re, R' and m are as hereinbefore defined, and B is as hereinbefore defined, with anhydrous hydrogen chloride in the presence of an inert organic solvent, e.g. chloroform at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

According to a further feature of the present invention, compounds of general formula ll, wherein A represents a group of general formula Ill, wherein R1 represents a straight- or branched-.chain alkyl group containing from 1 to 8 carbon atoms substituted by an alkanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 8 carbon atoms and maybe straight- or branched-chain and R2 represents a hydrogen atom, and B is as hereinbefore defined, (i.e. compounds of the general formula IIF herein depicted wherein R' and B are as hereinbefore defined and T" represents an alkanesulphonamido group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain) may be prepared by the reaction of a compound of general formula II, wherein A represents a group of general formula Ill, wherein R' represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by an unsubstituted aminocarbonyl group or a straight- or branchedchain alkenyl or alkynyl group containing from 2 to 8 carbon atoms, substituted by an unsubstituted aminocarbonyl group,(i.e. a compound of general formula IIE, wherein Rr and B are as hereinbefore defined and T represents an unsubstituted amino group), with an alkanesulphonylchloride, wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight-or branched-chain. The reaction may be effected at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture and optionally in the presence of a suitable inert organic solvent, for example a ketone, e.g. methylethylketone, or toluene, and optionally in the presence of a base, for example an alkali metal, e.g. potassium, carbonate.

According to a further feature of the present invention, compounds of general formula II, wherein A represents a group of formula Ill wherein R1 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms substututed by a hydroxy group or a straightor branched-chain alkenyl or alkynyl group containing from 3 to 8 carbon atoms substituted by a hydroxy group and R2 represents a hydrogen atom, and B is as hereinbefbre defined, (i.e.

compounds of the general formula IIG herein depicted wherein B is as hereinbefore defined and Be represents a straight- or branched-chain alkylene group containing from 2 to 8 carbon atoms or a straight- or branched-chain alkenylene or alkynylene group containing from 3 to 8 carbon atoms) may be prepared by the reduction of the carboxylic acid or ester group of a compound of the general formula XVII herein depicted wherein B is as hereinbefore defined, R' represents a straight- or branched-chain alkylene group containing from 1 to 7 carbon atoms or a straight- or branched-chain alkenylene or alkynylene group containing from 2 to 7 carbon atoms, Ru represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms and Tl represents a hydrogen atom or, when Ru represents an alkyl group, T1 may also represent a group R6(C = 0)-, wherein R6 is as hereinbefore defined. When Ru represents a hydrogen atom, the reduction is effected with sodium dihydrobis-(2-methoxyethoxy)aluminate in the presence of a suitable inert organic solvent, for example toluene, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture. When R" represents an alkyl group, the reduction is effected with sodium borohydride in the presence of methanol and of tertiary butanol as solvent, at the reflux temperature of the reaction mixture.

According to a further feature of the present invention, compounds of general formula II, wherein A represents a group of general formula Ill, wherein R1 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms substituted by a chlorine atom or a straight- or branched-chain alkenyl or alkynyl group containing from 3 to 8 carbon atoms substituted by a chlorine atom, and R2 represents a hydrogen atom, and B is as hereinbefore defined (i.e. compounds of the general formula IIH herein depicted, wherein B and R' are as hereinbefore defined, may be prepared by the reaction of a compound of general formula II, wherein A represents a group of general formula Ill, wherein R' represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms substituted by a hydroxy group or a straight- or branched-chain alkenyl or alkynyl group containing from 3 to 8 carbon atoms substituted by a hydroxy group and R2 represents a hydrogen atoms, and B is as hereinbefore defined, (i.e. a compound of general formula IIG wherein B and R' are as hereinbefore defined) with thionyl chloride, optionally in a suitable inert organic solvent, for example dichloromethane or trichloromethane, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

According to a further feature of the present invention, compounds of general formula II, wherein A represents a group of general formula Ill, wherein R1 represents an alkylthio group wherein the alkyl moiety contains from 1 to 4 carbon atoms and may be straight- or branched- - chain, and R2 represents a hydrogen atom, and B is as hereinbefore defined, (i.e. compounds of the general formula IlJ herein depicted wherein B is as hereinbefore defined and BV represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms) may be prepared by the reaction of an alkali metal, e.g. sodium or potassium, salt of a compound of general formula X, wherein B is as hereinbefore defined, with an alkanesulphenyl chloride, wherein the alkane moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain, for example with cooling, e.g. to O C, in the presence of a suitable inert organic solvent, e.g.

toluene, and optionally in the presence of a Crown ether, e.g. 15-Crown-5 or 18-Crown-6.

According to a further feature of the present invention, compounds of general formula Il, wherein A represents a group of general formula IIIA, wherein RP represents a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms, and Rq is as hereinbefore defined, and B is as hereinbefore defined (i.e. compounds of the general formula IIK herein depicted wherein B, BV and Rs are as hereinbefore defined) maybe prepared by the reaction of a compound of general formula X, wherein B is as hereinbefore defined) with a compound of the general formula XVIII herein depicted, wherein RV is as hereinbefore defined and R" represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, for example, in the presence of an acid catalyst, e.g. p-toluenesulphonic acid, optionally in the presence of a suitable inert organic solvent e.g. tetrahydrofuran or dioxan, at the reflux temperature of the reaction mixture.Reaction may be effected in the presence of a lower alkanol, e.g. methanol or ethanol, optionally in the presence of an inorganic acid, e.g., hydrochloric or sulphuric acid, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

According to a further feature of the present invention, compounds of general formula II, wherein A represents a group of general formula IIIA, wherein RP represents an amino group substituted by one or two straight- or branched-chain alkyl groups each containing from 1 to 4 carbon atoms and which may be the same or different, and Rq is as hereinbefore defined, and B is as hereinbefore defined, (i.e.

compounds of the general formula IIL herein depicted wherein Rx represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms and Rq and R" are as hereinbefore defined) may be prepared by reacting a compound of general formula II wherein A represents a group of general formula IIIA, wherein RP represents a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms and R4 is as hereinbefore defined, and B is as hereinbefore defined (i.e. a compound of general formula IIK wherein B, Rv and Rs are as hereinbefore defined) with a mono- or di-alkylamine wherein the alkyl moiety or moieties each contain from 1 to 4 carbon atoms and may be straight- or branched-chain and which, when the reaction is effected with a di-alkylamine, may be the same or different. The reaction may be effected in a suitable inert organic solvent, e.g. tetrahydrofuran, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture and preferably in the presence of an excess of the mono- or di-alkylamine.

According to a further feature of the present invention, compounds of general formula II, wherein A represents a group of general formula Ill wherein R1 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms unsubstituted or substituted in the alpha position by a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms and R2 represents a hydrogen atom, and B is as hereinbefore defined, (i.e. compounds of the general formula IIM herein depicted wherein B is as hereinbefore defined, RV represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 7 carbon atoms and T2 represents a hydrogen atom or a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms) may be prepared by the reduction of the imine double bond of a compound of the general formula XIX herein depicted wherein B, RV and T2 are as herein before defined.The reduction may be effected with an alkali metal, e.g. sodium boro- or cyanoborohydride in the presence of a suitable inert organic solvent, for example an alkanol containing from 1 to 4 carbon atoms, e.g. methanol or ethanol or tetrahydrofuran at a temperature of from O"C up to 60"C. When the reduction is effected under mild conditions, a compound of general formula Il wherein A represents a group of general formula Ill wherein R1 represents a straightor branched-chain alkyl group containing from 1 to 8 carbon atoms substituted in the alpha position by a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms (i.e.

a compound of general formula llM wherein T2 represents an alkoxy group) is obtained, while the useof more vigorous reduction gives a compound of general formula il wherein A represents a group of general formula lil wherein R1 represents an unsubstituted straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms and R2 represents a hydrogen atom, and B is as hereinbefore defined (i.e. compound of general formula IIM wherein T2 represents a hydrogen atom).When the reduction is effected in the presence of an alkanol, the reduction may be accompanied by alcoholysis of an alkoxy group represented by T2 in general formula XIX, to give a product wherein B1 is substituted in the alpha position by an alkoxy groúp corresponding to the alcohol used.

Accordingvto a further feature~of the present invention, compounds of general formula @@, wherein A represents a~ group of general formula IV, wherein Ba, Rb, RC, Rd, Re, Rf and mare as; hereinbefore defined and wherein B is as hereinbefore defined, may be prepared by the process which comprises the treatment with a base of a compound of the general formula XX herein depicted, wherein Ra., Rb, RC, Rd, R6, Rf, m and B are as hereinbefore defined and X1 represents a chlorine or bromine atom.Treatment with a base may be suitably effected with sodium hydride in a mixture of dichloromethane and dimethylformamide, potassium bicarbonate in ethanol and, optionally, water, potassium carbonate in acetone and, optionally, water, triethylamine in ethanol and, optionally, water or Triton B in ethanol and, optionally, water, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

Compounds of general formula XX may be prepared by the reaction of a compound of general fQrmuia X. wherein B is as hereinbefore defined, with a compound of the general formula XXI herein depicted, wherein X2 represents a chlorine or bromine atom and Ra, Rb, RC, Rd, Re, Rt, X1 and m are as hereinbefore defined, and X1 and X2 may be the same. or different, in the absence or presence of a suitable inert organic solvent, for example a ketone, e.g. acetone, an aromatic hydrocarbon, e.g. benzene or toluene, chloroform, dichloromethane or dimethylformamide, and optionally in the presence of an acid-binding agent, for example pyridine triethylamine or an alkali metal, e.g. sodium or potassium, carbonate or bicarbonate, at a temperature from 0CC up to the reflux temperature of the reaction mixture.

If desired, the compound of general formula XX may be prepared in situ by reaction of a compound of general formula X with a compound of general formula XXI and treated with a mild base to give a compound of general formula I, wherein A represents a group of general formula IV, wherein Ra, Rb, RC, Rd, R', and m are as hereinbefore defined, and wherein B is as hereinbefore defined, without isolation of the compound of general formula XX.

When, in a compound of general formula XX, one or both of BC and Rd represents a hydrogen atom and/or one or both of Ra and R' represents an alkyl group containing an alpha-hydrogen atom, treatment of the aforesaid compounds of general formula XX with a base may, according to the reaction conditions used, give rise, in addition to a compound of general formula II, wherein A represents a group of general formula IV, wherein Ba, Rb, RC, Rd, Re, Rf and m are as hereinbefore defined, and wherein B is as hereinbefore defined, to a compound in which the pyrazole ring carries, in the 5-position, an open-chain alkenylcarbonylamino group, by elimination of hydrogen chloride or hydrogen bromide with formation of an ethylenic double bond. For example, when in the compound of general formula XX, BC is as hereinbefore defined and Rd is hydrogen, a compound of the general formula XXII herein depicted, wherein Ba, Rb, RC, Re, Rf, m and B are as hereinbefore defined, may be obtained, in addition to a compound of general formula II, by the elimination of hydrogen chloride or hydrogen bromide with the formation of an ethylenic double bond, while when, in the compound of general formula XX, R" represents an alkyl group containing an alpha-hydrogen atom and R' represents a hydrogen atom or an alkyl group which does not contain an alpha-hydrogen atom, there may be obtained, in addition to a compound of general formula II, a compound of the general formula XXIII herein depicted, wherein Ra, Rb, RC,Rd, R', m and B are as hereinbefore defined and R9 and R10, which may be the same or different, each represent a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 3 carbon atoms, the total combined number of carbon atoms in R9 and R10 taken together being not more than three.As will be apparent to those skilled in the art, further compounds of similar structure may be formed by elimination of hydrogen chloride or hydrogen bromide with formation of an ethylenic double bond, for example when, in the compound of general formula XX, Rf represents an alkyl group containing an alpha-hydrogen atom and R" represents a hydrogen atom or an alkyl group which does not contain an alphahydrogen atom. Mixtures of compounds of general formula Il and compounds in which the pyrazole ring carries, in the 5-position, an open-chain alkenyl-carbonylamino group, e.g.

compounds of general formulae XXII and XXIII, thus obtained may be readily separated into their components of general formula Il and, for example, general formulae XXII or XXIII by methods known per se, for example by chromatography on silica, selective solvent extraction or fractional crystallisation.

According to a further feature of the present invention, compounds of general formula II wherein A represents a group of general formula Ill wherein R1 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms substituted by a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms or an aminocarbonyl group unsubstituted or substituted by one or two straight- or branchedchain alkyl groups each containing from 1 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups each containing from 2 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups, may be the same or different and R2 represents a hydrogen atom, and B is as hereinbefore defined (i.e. compounds of the general formula IIN herein depicted wherein B is as hereinbefore defined, BZ represents a straight- or branched-chain alkylene group containing from 2 to 8 carbon atoms and T3 represents a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 8 carbon atoms or an amino group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups each containing from 1 to 8 carbon atoms and which, when the amino group is substituted by two alkyl groups, may be the same or different or substituted by one or two straight- or branchedchain alkenyl or alkynyl groups each containing from 2 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups, may be the same or different), may be prepared by treating a compound of general formula 11 wherein A represents a group of general formula VI, wherein Ra, Rb, RC, Rd, Re, R' and m are as hereinbefore defined, with the proviso that the group of general formula IV contains from 2 to 8 carbon atoms excluding the carbon atom of the carbonyl group, and B is as hereinbefore defined, to effect fission of the amide group of the group of formula IV, with, respectively, an aqueous solution of an alkali metal, e.g. sodium or potassium, hydroxide, optionally in the presence of a lower alkanol, e.g. methanol, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture, a straight- or branched-chain alkanol containing from 1 to 8 carbon atoms in the presence of an alkali metal lower alkoxide, e.g. sodium methoxide, or ethanolic hydrogen chloride, optionally in the presence of water, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture, or ammonia or a mono- or di-alkylamine, wherein the alkyl moieties are straight- or branched-chain and each contain from 1 to 8 carbon atoms and may, in the case of a dialkylamine, be the same or different or a mono- or di-alkenyl- or alkynyl- amine wherein the alkenyl or alkynyl moieties are straight- or branched-chain and each contain from 2 to 8 carbon atoms and which may, in the case of a di- alkenyl- or alkynyl-amine, be the same or different, optionally in the presence of an inert organic solvent, e.g. toluene, tetrahydrofuran or dioxan, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

(By the term 'methods known per se' as used in the present specification is meant methods heretofore used or described in the chemical literature).

The compounds of general formula X, wherein B as hereinbefore defined, may be prepared by the process which comprises the cyclisation of a compound of the general formula XXIV herein depicted, wherein B is hereinbefore defined. Cyclisation may be effected in the presence of an inert organic solvent, for example an alcohol containing from 1 to 4 carbon atoms, e.g.

ethanol,acetic acid or ethoxyethanol, at a temperature of from ambient temperature to the reflux temperature of the reaction mixture.

Compounds of general formula XXIV may be prepared by the reaction of a compound of the general formula IX herein depicted, wherein B is as hereinbefore defined, or an acid addition salt thereof, e.g. the hydrochloride, with a compound of the general formula XXV herein depicted, wherein R4 is as hereinbefore defined.

The reaction of a compound of general formula IX with a compound of general formula XXV may be effected in the presence of an inert organic solvent, for example an alkanol containing from 1 to 4 carbon atoms, e.g. ethanol, acetic acid or ethoxyethanol, and at a temperature from ambient temperature to the reflux temperature of the reaction mixture and optionally in the presence of an alkali metal,e.g. sodium or potassium, acetate, carbonate or bicarbonate. When an acid addition salt of the compound of general formula IX is used, the reaction with the compound of general formula XXV is effected in the presence of an alkali metal, e.g. sodium or potassium, acetate, carbonate or bicarbonate.

The compounds of general formula X may be prepared by reaction of a compound of general formula IX with a compound of general formula XXV without isolation of an intermediate compound of general formula XXIV from the reaction mixture. When the reaction of a compound of general formula IX with a compound of general formula XXV is effected in acetic acid, in the absence or presence of an alkali metal, e.g. sodium or potassium, acetate, the intermediate compound of general formula XXIV may separate from the reaction mixture, depending upon the solubility of the intermediate compound of general formula XXIV in the reaction medium, and may, if desired, be isolated before being cyclised as hereinbefore described to a compound of general formula X, preferably by heating in an inert organic solvent, e.g. ethoxyethanol, at the reflux temperature of the reaction mixture.

Compounds of general formula XII, wherein R4, R5, and B are as hereinbefore defined, maybe prepared by reaction of a compound of general formula X, wherein B is as hereinbefore defined, with a compound of the general formula XXVI herein depicted, wherein R5 and B6 are as hereinbefore defined. Reaction may be effected in the presence of a lower alkanol, e.g.

methanol or ethanol, optionally in the presence of an inorganic acid, e.g. hydrochloric or sulphuric acid, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

Compounds of general formula XIX, wherein B, Rv and T2 are as hereinbefore defined, may be prepared by the reaction of a compound of the general formula X, wherein B is as herein before defined, with- a compound of the general formula XXVII herein depicted, wherein RV is as hereinbefore defined to give a compound of general formula XIX wherein T2 is a hydrogen atom, or with a compound of general formula XVIII, wherein Rv and R" are as herein before defined, to give a compound of general formula XIX wherein T2 is an alkoxy group. The reaction may be effected under the conditions herein before described for the reaction of a compound of general formula X with a compound of general formula XXVI.

Compounds of general formula XIII, wherein R1, R6 and B are as hereinbefore defined, may be prepared by the reaction of a compound of the general formula XXVIII herein depicted, wherein R6 and B are as hereinbefore defined, or an alkali metal, e.g. sodium or potassium, derivative thereof,- with a compound of the general formula Xl, wherein B1 and X are as hereinbefore defined. Reaction may be effected in a suitable inert organic solvent, e.g.

dichloromethane, tetrahydrofuran, dimethylformamide, at a temperature from laboratory temper atureto the reflux temperature of the reaction mixture, and, when a compound of general formula XXVIII is used, in the presence of a base e.g. Triton B.

Alkali metal derivatives of compounds of general formulae X and XXVIII may be prepared in situ by the reaction of a compound of general formulae X or XXVI II, where B and B6 and B, respectively, are as hereinbefore defined, with an alkali metal, e.g. sodium or potassium, hydride, at a temperature from laboratory temperature to the reflux temperature of the reaction mixture.

Compounds of general formula XXVIII, wherein R6 and B are as hereinbefore defined, may be prepared by the reaction of a compound of general formula X, wherein B is as hereinbefore defined with a compound of the general formula XXIX herein depicted, wherein R6 and X1 are as hereinbefore defined, or with a compound of the general formula XXX herein depicted, wherein B6 is as hereinbefore defined, in the absence or presence of a suitable inert organic solvent, for example a ketone, e.g. acetone, an aromatic hydrocarbon, e.g. benzene or toluene, chloroform, dichloromethane or dimethylformamide, and optionally in the presence of an acid-binding agent, for example pyridine, triethylamine or an alkali metal, e.g. sodium or potassium, carbonate or bicarbonate, at a temperature from O"C to the reflux temperature of the reaction mixture.

Compounds of general formula XIV may be prepared by the reaction of a compound of general formula X wherein B is as herein before defined, with a compound of the general formula XXXI herein depicted, wherein R7 and X1 are as hereinbefore defined, or with a compound of the general formula XXXII herein depicted, wherein R7 is as hereinbefore defined. The reaction may be effected as herein before described for the reaction of a compound of general formula X with a compound of general formulae XXIX or XXX.

Compounds of general formula XVII wherein T1 represents a hydrogen atom may be prepared by procedures herein described for the preparation of compounds of general formula II, wherein A represents a group of general formula III wherein R1 represents an alkyl, alkenyl or alkynyl group substituted by a carboxy or alkoxycarbonyl group and R2 represents a hydrogen atom, and B is as herein before defined. Compounds of general formula XVII wherein T1 represents a group R6(C = 0) may be prepared by the procedure herein described for the preparation of compounds of general formula XIII.

Compounds of general formulae VIII, IX, Xl, XVI, XVIII, XXI, XXV, XXVI, XXVI I, XXIX, XXX, XXXI and XXXI I maybe prepared by methods known per se.

Compounds of general formula XXVIII, wherein R6 represents a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms, (i.e. compounds of the general formula XXXII I herein depicted, wherein B11 represents a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms and B is as herein before defined) may be prepared by the reaction of a compound of the general formula XXXIV herein depicted, wherein R12 represents a phenoxy group and B is as hereinbefore defined, with a compound of the general formula XXXV herein depicted, wherein B11 is as hereinbefore defined.The reaction may be effected in water or a suitable inert aqueous-organic or organic solvent, for example an alkanol containing from 1 to 4 carbon atoms, e.g. ethanol, or an aromatic hydrocarbon, e.g. benzene or toluene, or which is preferably in excess of the compound of general formula XXXV, at a temperature of from ambient temperature upto the reflux temperature of the reaction mixture and, if necessary, at elevated pressure, and optionally in the presence of a base, for example an alklai metal alkoxide, e.g. of the compound of general formula XXXV.

Compounds of general formula XXXIV may be prepared by the reaction of a compound of general formula X, wherein B is as herein before defined, with a compound of the general formula XXXVI herein depicted, wherein R72 and X1 are as hereinbefore defined. The reaction may be effected as hereinbefore described for the reaction of a compound of general formula X with a compound of general formula XXIX.

Compounds of general formula XXXV and XXXVI may be prepared by methods known per se.

Salts with agriculturally acceptable bases of compounds of general formula II, wherein A represents a group of general formula III wherein R1 and/or R2 represents an alkyl, alkenyl or alkynyl group substituted by a carboxy group may be prepared from the corresponding compounds of general formula Il by methods known per se, for example by reacting stoichiometric quantities of the compounds of general formula II and the appropriate base, for example, an alkali metal hydroxide, carbonate or bicarbonate, an alkaline earth metal hydroxide or carbonate, ammonia or an amine (e.g. diethanolamine, triethanolamine, octylamine, morpholine or dioctylamine), in a suitable solvent. The salts may, if necessary be purified by recrystallisation from one, two or more suitable solvents.

As well as being useful in themselves as herbicidally active compounds, salts of compounds of general formula II may also be used in the purification of the corresponding compounds of general formula II, for example by exploitation of the solubility difference between the'salts and the parent compounds in water and in organic solvents, by techniques which are well known to those skilled in the art.

By the term 'lower alkanol' and 'alkali metal lower alkoxide' as used herein are meant alkanols and alkali metal alkoxides containing from 1 to 4 carbon atoms.

The compounds which are obtained from compounds of general formula XX in which the pyrazole ring carries, in the 5-position, an open-chain alkenylcarbonylamino group, by elimination of hydrogen chloride or hydrogen bromide with formation of an ethylenic double bond, for example compounds of general formulae XXII and XXI II, wherein R8, Rb, RC, Rd, R6, R', R9, R10, m and B are as hereinbefore defined, possess herbicidal properties similar to those of the compounds of general formula 11.

The following Examples and Reference Examples illustrate the preparation of compounds of general formula II. (In the following Examples and Reference Examples, chromatography was effected on a silica column (Merck 0.040-0.063mm) at a pressure of 6.8 N.m.-2, unless otherwise indicated].

EXAMPLE 23 (Preparation of Compounds Nos 1 to 5) A solution of 4-cyano-5-(N-ethyl-N-methoxycarbonyl)-amino- 1 -(2,3,4,-trichlorophenyl)pyrazole (49) and aqueous sodium hydroxide solution (10.66ml; (N) in methanol (200ml) was kept at laboratory temperature for 4 days.The solution was then evaporated under diminished pressure and the residue was dissolved in dichloromethane (100ml). The dichloromethane solution was washed with water (3 X 50ml) and dried over anhydrous sodium sulphate and evaporated to give a residue which was crystallised from a mixture of toluene and hexane (60my; 1:1) to give 4-cyano-5-ethylamino-1-(2,3,4,-trichlorophenyl)pyrazole (1.9g), m.p. 145"C, in the form of colourless crystals.

By proceeding in a similar manner but replacing the 4-cyano-5-(N-ethyl-N-methoxycarbony l)amino-1-(2,3,4,-trichlorophenyl)pyrazole by the hereinafter indicated appropriately substituted phenylpyrazole, there were prepared: 4-Cyano-5-n-propylamino-1-(2,3,4,-trichlorophenyl)pyrazole, m.p. 89-90"C, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from 4cyano-5-(N-methoxycarbonyl-N-propyl)amino- 1 -(2,3,4,-trichlorophenyl)pyrazole.

4-Cyano-5-methylamino-1-(2,3,4,-trichlorophenyl)pyrazole, m.p. 161-163eC, in the form of colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from 4 cyano-5-(N-methoxycarbonyl-N-methyl)-amino- 1 -(2, 3,4,-trichlorophenyl)pyrazole.

4-Cyano-5gprop-2-enyl)amino-142,3,4,-trichlorophenyl)pyrazole, m.p. 120-121 ec, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from 4-cyano-5-(N-methoxy-carbonyl-N-prop-2-enyl)amino-1 -(2, 3,4,-trichlorophenyl)pyrazole.

4-Cyano-5-(prop-2-ynyl)amino-1 -(2, 3,4,-trichlorophenyl)pyrazole, m.p. 133.5-135 C, after crystallisation from a mixture of ethyl acetate and hexane, in the form of a colourless solid, from 4-cyano-5-(N-methoxycarbonyl-N-prop-2-ynyl)amino-1-(2,3,4,-trichlorophenyl)pyrazole.

EXAMPLE 24 (Preparation of Compounds Nos 6, 7 and 23 to 38) A mixture of 5-(N-acetyl-N-isopropyl)amino-4-cyano-1-(2,3,4,-trichlorophenyl)pyrazole (1.55g) and aqueous sodium hydroxide (4ml; 1 N) in methanol (50ml) was stirred at laboratory temperature for 48 hours. The solution was then evaporated to dryness and the residue was dissolved in dichloromethane (100ml). The dichloromethane solution was washed with water (2 X 200ml) and dried over anhydrous magnesium sulphate and evaporated to give a solid which was crystallised from a mixture of ethyl acetate and hexane to give 4-cyano-5 isopropylamino-1-(2,3,4,-triclorophenyl)pyrazole (0.75g), m.p. 141-142.5 C, in the form of a colourless solid.

By proceeding in a similar manner but replacing the 5-(N-acetyl-N-isopropyl)amino-4-cyano-1- (2,3,4,-trichlorophenyl)pyrazole by the hereinafter indicated appropriately substituted phenylpyrazole, there were prepared: 5-n-Butylamino-4-cyano-1-(2,3,4,-trichlorophenyl)pyrazole, in the form of a pale yellow gum, from 5-(N-acetyl-N-n-butyl)amino-4-cyano-1-(2,3,4,-trichlorophenyl)pyrazole.

5-iso-Butylamino-4-cyano-1-(2,3,4,-trichlorophenyl)pyrazole, m.p. 156-159"C, in the form of colourless crystals, following chromatography using dichloromethane as eluent, from 5-(N-acetyl N-iso-butyl)amino-4-cyano- 1 -(2, 3,4,-trichlorophenyl)pyrazole.

5-sec-Butylamino-4-cyano-1-(2,3,4,-trichlorophenyl)pyrazole, m.p. 114-117"C, in the form of colourless crystals, following chromatography using dichloromethane as eluent, from 5-(N-acetyl N-sec-butyl)amino-4-cyano-1 -(2,3,4,-trichlorophenyl)pyrazole.

5-sec-Butylamino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-pyrazole, in the form of a pale yellow glass, following chromatography using diethyl ether--hexane (1:1) as eluent, from 5-(Nacetyl-N-sec-butyl)amino- 1 -(2-chloro-4-trifl uoromethyl phenyl)-4-cyanopyrazole.

1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-iso-propylaminopyrazole, m.p.- 124-1 26'C, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-(N-acetyl-N-iso-propyl)amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole.

1 -(2-Chloro-4-trifluoromethylphenyl-4-cyano-5-methyl-aminopyrazole, m. p. 11 4-11 6 'C, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-(N-acetyl-N-methyl)amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole.

5-n-Butylamino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, m. p. 75-76"C, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-(N-acetyl-N-n-butyl)amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole.

5-iso-Butylamino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, in the form of a pale yellow glass, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-(Nacetyl-N-iso-butyl)-amino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole.

1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-n-propylaminopyrazole, m. p. 121 -1234C, in the form of colourless crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-(N-acetyl-N-npropyl)amino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole.

1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-ethylaminopyrazole, m. p. 1 26-1 27 'C, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-(N-acetyl-N-ethyl)-a mi no- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole.

4-Cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-methylaminopyrazole, m p. 122-124.5 C, in the form of a colourless solid, after crystallisation from ethyl acetate, from 5-(N-acetyl-Nmethyl)amino-4-cyano- 1 -(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole.

4-Cyano-5-ethylamino- 1 -(4-ethyl-2, 3,5, 6-tetrafluorophenyl)pyrazole, m p. 101.5-103.5 'C, in the form of an off-white solid, from 5-(N-acetyl-N-ethyl)amino-4-cyano-1-(4-ethyl-2,3,5,6-tetraflu- orophenyl)pyrazole.

4-Cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-n-propylaminopyrazole, m.p. 100.5-102 C, in the form of an off-white solid, from 5-(N-acetyl-N-n-propyl)amino-4-cyano-1-(4-ethyl-2,3,5,6- tetrafluorophenyl)pyrazole.

4-Cyano-1-(2,4-dichlorophenyl)-5-n-propylamino-pyrazole, in the form of a brown gum, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-(1-N-acetyl-N-n-propy I)amino-4-cyano-1 -(2,4-dichlorophenyl)pyrazole.

4-Cyano-1-(2,4-dichlorophenyl)-5-methylamino-pyrazole, m.p. 195-197"C, in the form of colourless crystals, after crystallisation from toluene, from 5-(N-acetyl-N-methyl)amino-4-cyano-1 (2,4-dichlorophenyl)pyrazole.

4-Cyano-1-(2,4-dichlorophenyl)-5-iso-propylaminopyrazole, in the form of an brown gum, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-(N-acetyl-N-isopropyl)amino-4-cyano-1 -(2,4-dichlorophenyl)pyrazole.

4-Cyano- 1 -(2,4-d ichlorophenyl)-5-ethylaminopyrazole, m.p. 104.5-106.5'C, in the form of colourless crystals, following chromatography using ethyl acetate-hexane (1:3) as eluent, from 5.(N-acetyl-N-ethyl)amino-4-cyano-1 -(2,4-dichlorophenyl)pyrazole.

EXAMPLE 25 (Preparation of Compounds Nos 39, 2, 40, 41 and 42) 5-Amino-4-cyano-1 -(2, 3,4,-trichlorophenyl)pyrazole (2.879; described in British Published Patent Specification 2,070,604A) was added in one portion to a stirred suspension of powdered sodium hydride (0.60g) in dry tetrahydrofuran (25ml). When evolution of hydrogen had ceased 15Crown5 (0.1 ml) and n-propyl iodide (4.259) were added successively with stirring at a temperature of 1 5CC to 20'C maintained by external cooling. The reaction mixture was then stirred at laboratory temperature for 16 hours and then evaporated under diminished pressure.

The residue was dissolved in a mixture of dichloromethane (100ml) and water (100ml). The organic layer was separated, washed with water (100ml), and then was dried over anhydrous magnesium sulphate and evaporated to give a clear oil (3.809). This oil was chromatographed using diethyl ether-hexane (1:1) as eluate. Evaporation of the eluent containing the faster moving component gave 4-cyano-5-di(n-propyl)amino-1-(2,3,4,-trichlorophenyl)pyrazole (2,2 g), m.p. 99-100oC, in the form of a colourless solid.

Evaporation of the eluate containing the slower moving component gave 4-cyano-5-n propylamino-1-(2,3,4,-trichlorophenyl)pyrazole (0.809), m.p. 95-98'C, in the form of creamcoloured crystals, after crystallisation from a mixture of diethyl ether and hexane.

By proceeding in a similar manner but replacing the n-propyl iodide by an excess of methyl iodide and using potassium tertiary butoxide/ 1 8-Crown-6 as base in place of sodium hy dride/l 5-Crown-5. there was prepared: 4-Cyano-5-dimethylamino-1 -(2,3,4,-trichlorophenyl)pyrazole, m.p. 1 27-129 CC, in the form of colourless crystals, after crystallisation from toluene.

By proceeding in a similar manner but replacing the n-propyl iodide by ethyl bromoacetate there was prepared : 4-Cyano-5-ethoxycarbonylmethylamino-1-(2,3,4,-trichlorophenyl)pyrazole, m.p. 122-123 C, in the form of a colourless solid, after crystallisation from a mixture of toluene and hexane, following chromatography using diethyl ether-hexane (1:1) as eluent.

By proceeding in a similar manner but replacing the 5-amino-4-cyano-1-(2,3,4,-trichlorophenyl)pyrazole by 5-amino-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole (described in British Published Patent specification 2105325A there was obtained : 4-Cyano-5-n-propylamino-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, m.p.

107-108 C, in the form of colourless crystals, after crystallisation from a mixture of diethyl ether and hexane, following chromatography using diethyl ether-hexane (1:1) as eluent.

EXAMPLE 26 (Preparation of Compounds Nos 43 to 46) A mixture of 5-(N-acetyl-N-ethoxycarbonylmethyl)-amino-4-cyano- 1 -(2,3,4,-trichlorophenyl)py- razole (2.469) and aqueous sodium hydroxide (1 Oml, 3N) in methanol (40ml) was stirred at laboratory temperature for 24 hours. The solution was evaporated to dryness and the residue was dissolved in water (100ml). The aqueous solution was acidified to pH 1 with concentrated hydrochloric acid to precipitate a solid. The solid was filtered off and washed with water and then dried over silica gel in a desiccator to give 5-carboxymethylamino-4-cyano-1-(2,3,4,trichlorophenyl)pyrazole (containing 0.29 mole of water of crystallisation), m.p. 87 C (with decomposition) in the form of a colourless solid.

By proceeding in a similar manner but replacing the 5-(N-acetyl-N-ethoxycarbonylmethyl)amino-4-cyano-1-(2,3,4,-trichlorophenyl)pyrazole by the hereinafter appropriately substituted phenylpyrazole there were prepared: 5-Carboxymethylamino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, m . p. 97-99 CC, in the form of a colourless solid, from 5-(N-acetyl-N-ethoxycarbonylmethyl)-amino-1 -(2-chloro-4trifluoromethylphenyl)-4-cyanopyrazole.

5-Carboxymethylamino-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole (containing 0.25 mole of water of crystallisation), m.p. 75 C (with decomposition) in the form of buff-coloured foam, from 5-(N-acetyl-N-ethoxy-carbonylmethyl)amino-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole.

5-Carboxymethylamino-4-cyano-1 -(2,4,6-trichlorophenyl)pyrazole (containing 0.25 mole of water of crystallisation) m.p. 161-1 64CC, in the form of a colourless solid, from 5-(N-acetyl-Nethoxy-carbonylmethyl)amino-4-cyano-1 -(2,4, 6-trichlorophenyl)pyrazole.

EXAMPLE 27 (Preparation of Compound No 47) A mixture of 5-(N-acetyl-N-ethoxycarbonylmethyl)-amino-4-cyano- 1 -(2,3,4-trichlorophenyl)pyra- zole (10g) and sodium borohydride (2.3g) in dry tertiary butanol (100ml) was heated at reflux while methanol (20ml) ws added over 30 minutes. The reaction mixture was refluxed for a further 3 hours and then stored at laboratory temperature overnight.Water (300ml) was then added and the precipitate was filtered off, washed with water and dried at 100"C to give a colourless powder (6.019; m.p. 197-199 C) which was recrystallised from ethanol (250ml) to give 4-cyano-5-(2-hydroxyethyl)amino- -(2,3,4-trichlorophenyl)pyrazole (3.29), m . p.

203-204"C, in the form of colourless crystals.

EXAMPLE 28 (Preparation of Compound No 48) A solution of 4-cyano-5-(2-hydroxyethyl)amino-l -(2,3,4-trichlorophenyl)pyrazole (3.0g); prepared as described in Example 27) in thionyl chloride (25ml) was heated under reflux for 5 hours. The solution was evaporated under reduced pressure and the residue was dissolved in dichloromethane (100ml). The dichloromethane solution was washed with water (2 X 200ml), dried over anhydrous magnesium sulphate and evaporated to give an orange gum, which was chromatographed using dichloromethane as eluent. Evaporation of the eluate containing the major component gave 5-(2-chloroethyl)amino-4-cyano- 1 -(2,3,4-trichlorophenyl)pyrazole, m.p.

125-128'C, in the form of a cream-coloured solid.

EXAMPLE 29 (Preparation of Compounds Nos 49 to 64) (a) A solution of 5-carboxymethylam ino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole (4.59; prepared as described in Example 26) in thionyl chloride (40ml) was heated at reflux for 1 hour. The reaction mixture was cooled and evaporated under diminished pressure to give 5 chlorocarbonylmethylam no- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole (4.7 2g), in the form of a red oil, which was used immediately in b or c below: (b) 5-Chlorocarbonylmethylamino-1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole (4.729) was dissolved in dry ethanol (40ml) and the solution heated under reflux for 1 6 hours.

The reaction mixture was evaporated to give a gum which then was dissolved in diethyl ether (200ml) and washed successively with aqueous 2N sodium carbonate solution (2 X 50ml) and water (2 X 50ml). The organic layer was dried over anhydrous sodium sulphate and evaporated to give a red gum, which was chromatographed using dichloromethane as eluent. Evaporation of the eluate containing the major component gave a yellow oil (1.79) which was crystallised from a mixture of toluene (lOml) and hexane (50ml) to give 1-(2-chloro-4-trifluoromethylphenyl)- 4-cyano-5-ethoxy-carbonylmethylaminopyrazole (1.39), m.p. 100-102 C, in the form of colourless crystals.

By proceeding in a similar manner but replacing the ethanol with the hereinafter indicated alkanol there were prepared: 1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-methoxyCarbonylmethylaminopyrazole, m.p.

120-1-21 C, in the form of colourless crystals, after crystallisation from toluene, from methanol.

1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-n-propoxyCarbonylmethylaminopyrazole, m.p.

88-89 C, in the form of colourless crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane as eluent, from n-propyl alcohol.

1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-iso-propoxyCarbonylmethylaminopyrazole, m p.

110-112 C, in the form of colourless crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane as eluent, from isopropyl alcohol.

5-n-Butoxycarbonylmethylamino-1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, m. p.

78-80 C, in the form of colourless crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane as eluent, from n-butanol.

1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-n-pentyloxycarbonylmethylaminopyrazole, m. p.

67-68 C, in the form of colourless crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane as eluent, from n-amyl alcohol.

1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-n-hexyloxycarbonyl methyla minopyrazole, m p.

64-66 C, in the form of colourless crystals, after crystallistion from a mixture of toluene and hexane, following chromatography using dichloromethane as eluent, from n-hexanol.

(c) A solution of 5-chlorocarbonylmethylamino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano- pyrazole (4.729) in dry methyl ketone (25ml) was added over 5 minutes to a stirred solution of ethylamine (20ml) in methyl ethyl ketone (100ml) at 0 C (maintained by external cooling). The resulting suspension was stirred for 1 hour whilst the reaction mixture attained laboratory temperature. The reaction mixture was evaporated to dryness and the residue was dissolved in a mixture of diethyl ether (100ml) and water (100ml). After separation of the organic layer, the organic layer was washed successively with aqueous 2N hydrochloric acid (2 X 100ml) and water (3 X 50ml) and dried over anhydrous sodium sulphate. Evaporation of the solution to dryness gave a fawn coloured powder (3.6g.m.p. 144-145 C) which was chromatographed using dichloromethane-ethyl acetate (4:1) as eluent. Evaporation of the eluate containing the major component gave a yellow oil which was crystallised from a mixture of toluene (5ml) and hexane (40ml) to give 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-ethylaminocarbonylmethy laminopyrazole, m.p. 150-151 C in the form of colourless crystals.

By proceeding in a similar manner but replacing the ethylamine by the hereinafter indicated amine there were prepared: 5-Carbamylmethylam ino-1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, m p.

174-175 C, in the form of colourless crystals, after crystallisation from toluene, from gaseous ammonia.

1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-methylaminocarbonylmethylaminopyrazole, m.p 213-214 C, in the form of colourless crystals, after crystallisation from ethanol, from gaseous methylamine.

1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-n-propylaminocarbonylmethylaminopyrazole, m.p. 122-124 C, in the form of colourless crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane-ethyl acetate (4:1) as eluent, from n-propylamine.

1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-diethylaminocarbonylmethylaminopyrazole, m.p. 83-85 C, in the form of colourless crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane-ethyl acetate (4:1) as eluent, from diethylamine.

1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-n-pentylam inocarbonylmethylam inopyrazole, m.p. 123-124 C, in the form of fawn-coloured crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane-ethyl acetate (4:1) as eluent from n-amylamine.

1 -(2-Chloro-4-trifl uoromethylphenyl)-4-cyano-5-n-hexylaminocarbonyl methylaminopyrazole, m.p. 1 39-140'C, in theform of off-white crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane containing gradually increasing proportions of ethyl acetate (0-10%) as eluent, from n-hexylamine.

1 -(2-Chloro-4-trifl uoromethylphenyl)-4-cyano-5-n-octylaminocarbonyl methyl am inopyrazole, m.p. 106-108'C, in the form of off-white crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane containing gradually increasing proportions of ethyl acetate (0-10%) as eluent, from n-octylamine.

1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-(morpholin-4-yl)-carbonylmethylaminopyrazole, m.p. 1 56-1 57 CC, in the form of fawn-coloured crystals, after crystallisation from ethanol, from morpholine.

EXAMPLE 30 (Preparation of Compound No 65) A suspension of 5-(N-tert-butoxycarbonyl-N-ethyl)-amino-4-cyano- 1 -(2,3,5, 6-tetrafl uoro-4-triflu- oromethylphenylpyrazole (2.599) in methanol (25ml) was heated under reflux and concentrated hydrochloric acid (2ml) was added. The reaction mixture was heated under reflux for 7 hours and then allowed to stand at laboratory temperature for 48 hours. The resulting solution was evaporated to dryness and the residue was dissolved in dichloromethane (100ml).The dichloromethane solution was washed with water (2 x 100ml), dried over anhydrous magnesium sulphate and evaporated to give a colourless solid (1.83g) which was crystallised from a mixture of diethyl ether and hexane (60ml, 1:1) to give 4-cyano-5-ethylamino-1-(2,3,5,6tetrafluoro-4-trifluoromethylphenyl)pyrazole, m.p. 1 68 CC, in the form of colourless crystals.

REFERENCE EXAMPLE 1 The hereinafter indicated compounds used as starting materials in Example 23 and 24 were prepared as follows: A mixture of 4-cyano-5-methoxycarbonylamino-1-(2,3,4-trichlorophenyl)pyrazole (4,1g), methyl iodide (4ml) and Triton B (5.9ml) in dichloromethane (30ml) was heated at reflux and stirred for 48 hours. The cooled reaction mixture was washed with water (2 X 150ml) and evaporated to dryness. The residue was chromatographed using diethyl etherhexane (1:1) as eluent. Evaporation of the eluate containing the major component gave 4-cyano-5-(N-methoxy carbonyl-N-methyl)amino-l -(2, 3,4-trichlotophenyl)pyrazole (2.19), m.p. 131-133"C, in the form of a colourless solid.

By proceeding in a similar manner but replacing the methyl iodide by the hereinafter indicated alkyl halide, there were prepared: 4-cyano-5-(N-ethyl-N-methoxycarbonyl)amino- 1 -(2,3,4-trichlorophenyl)pyrazole, m p.

111-11 2CC, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from ethyl iodide.

4-cyano-5-(N-methoxycarbonyl-N-prop-2-enyl)amino-1-(2,3,4-trichlorophenyl)pyrazole, m.p.

117-11 geC, in the form of a colourless solid, after chromatography using diethyl ether-hexane (1:1) as eluent, from allyl iodide.

By proceeding in a similar manner, but replacing the 4-cyano-5-methoxycarbonylamino-1 (2, 3,4-trichlorophenyl)pyrazole by 5-acetamido-4-cyano- 1 -(2,3,4-trich lorop henyl)pyrazole (des- cribed in British Published Patent Specification No 2101 999A) and replacing the methyl iodide by the hereinafter indicated alkyl halides, there were prepared: 5-(N-Acetyl-N-isopropyl)amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, m.p. 144-146 C, in the form of a colourless solid following chromatography using hexane-diethyl ether (1:1) as eluent, from isopropyl iodide.

5-(N-Acetyl-N-n-butyl)amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, m.p. 94-95'C, in the form of colourless crystals, following chromatography using dichloromethane-ethyl acetate (4:1) as eluent, from n-butyl iodide.

REFERENCE EXAMPLE 2 The hereinafter indicated compounds used as starting materials in Example 23 were prepared as follows: Powdered sodium hydride (0.5g) was added to a solution of 4-cyano-5-methoxycarbonylamino-1-(2,3,4-trichlorophenyl)pyrazole (7.0g) in dry tetrahydrofuran (50ml). When evalution of hydrogen had ceased n-propyl iodide (6.8g) was added and the resultant mixture was heated at reflux for 48 hours. The reaction mixture was then evaporated under diminished pressure and the residue was dissolved in dichloromethane and washed with water (4 X 100ml).The organic layer was dried over anhydrous magnesium sulphate and evaporated to give a solid which was crystallised from a mixture of ethyl acetate and hexane to give 4-cyano-5-(N-methoxycarbonyl-N propyl)-amino-1-(2,3,4-trichlorophenyl)pyrazole (5.5g), m.p. 116-117"C, in the form of a colourles solid.

By proceeding in a similar manner but replacing the n-propyl iodide by the hereinafter indicated alkyl halide, there were prepared: 4-Cyano-5-(N-methoxycarbonylamino-N-prop-2-ynyl)-1-(2,3,4-trichlorophenyl)pyrazole, in the form of a viscous yellow oil, following chromatography using diethyl ether-hexane (1:1) as eluent, from propargyl bromide.

By proceeding in a similar manner but replacing the 4-cyano-5-methoxycarbonylamino-1 (2,3,4-trichlorophenyl)pyrazole by the hereinafter indicated appropriately substituted 5-acetamidopyrazole and replacing the methyl iodide by the hereinafter indicated alkyl halide or alkyl haloester there were prepared: (i) Using 5-acetamido-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole:- 5-(N-Acetyl-N-iso-butyl)amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, m. p. 11 4-11 7 CC in the form of colourless crystals, following chromatography using diethyl ether-hexane (1:1) as eluent, from iso-butyl iodide.

5-(N-Acetyl-N-sec-butyl)amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, m. p. 129-131-C, in the form of colourless crystals, following chromatography using diethyl ether-hexane (1:1) as eluent, from sec-butyl iodide.

(ii) Using 5-acetamido-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole (described in British Published Patent Specification No 2101999A): 5-(N-Acetyl-N-methyl)amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, in the form of a brown oil, from methyl iodide.

5-(N-Acetyl-N-n-propyl)amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, in the form of a solid, from n-propyl iodide.

5-(N-Acetyl-N-ethyl)amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, in the form of a yellow oil, from ethyl iodide.

(iii) Using 5-acetamido-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole (described in British Published Patent Specification No 2101999A): 5-(N > Acetyl-N-methyl)amino-4-cyano- 1 -(4-ethyl-2, 3,5, 6-tetrafluorophenyl)pyrazole, m . p.

120.5-121.5 C, in the form of colourless crystals, after crystallisation from ethanol, from methyl iodide.

5-(N-Acetyl-N-ethyl)amino-4-cyano- 1 -(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole, m . p.

91-92.5 C, in the form of an off-white solid, from ethyl iodide.

5-(N-Acetyl-N-n-propyl)amino-4-cyano-1 -(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole, m . p.

92-94"C, in the form of colourless crystals, after crystallisation from ethanol, from n-propyl iodide.

By proceeding in a similar manner but carrying out the reaction in dioxan in place of tetrahydrofuran and replacing the 4-cyano-5-methoxycarbonylamino-1-(2,3,4-trichlorophenyl)py- razole by the hereinafter indicated appropriately substituted 5-amidopyrazoie and replacing the methyl iodide by the hereinafter indicated alkyl halide, there were prepared: (iv) Using 5-acetamido- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole (described in British Published Patent Specification No 2101999A: 5-(N-Acetyl-N-sec-butyl)amino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, m p.

118-1 22CC, in the form a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from sec-butyl iodide.

5-(N-Acetyl-N-iso-propl)-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, m.p.

1 33-1 34CC, in the form of colourless crystals, following chromatography using diethyl ether-hexane (1:1) as eluent, from iso-propyl iodide.

5-(N-Acetyl-N-n-butyl)amino- 1 (2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, in the form of a brown oil, from n-butyl iodide.

5-(N-Acetyl-N-iso-butyl)amino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, in the form of a brown gum, from iso-butyl iodide.

5-(N-Acetyl-N-ethoxycarbonyl methyl)amino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, m.p. 125-127'C, in the form of colourless crystals, after crystallisation from toluene, from ethyl bromoacetate.

(v) Using 5-acetamido-4cyano-1-(2,4-dichlorophenyl)pyrazole (described in British Published Patent Specification No. 2101999A): 5-(N-Acetyl-N-n-propyl)amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole, m.p. 101-102-C, in the form of colourless crystals, after crystallisation from ethanol, from n-propyl iodide.

5-(N-Acetyl-N-methyl)amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole, in the form of a green oil, from methyl iodide.

5-(N-Acetyl-N-ethyl)amino-4-cyano-1 -(2,4-dichlorophenyl)pyrazole, m.p. 104-105 CC, in the form of colourless crystals, after crystallisation from ethanol, from ethyl iodide.

(vi) Using 5-acetamido-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole:- 5-(N-Acetyl-N-ethoxycarbonylmethyl)am ino-4-cyano- 1 -(2,3,4-trichlorophenyl)pyrazole, m. p.

1 22-1 24CC, in the form of colourless crystals, after crystallisation from toluene, from ethyl bromoacetate.

(vii) Using 5-acetam ido-4-cyano- 1 -(4-ethyl-2,3,5, 6-tetrafi uorophenyl)pyrazole (described in British Published Patent Specification No. 2101999A): 5-(N-Acetyl-N-ethoxycarbonylmethylamino)-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole, m.p. 77-78.5 C, in the form of an off-white solid, after crystallisation from ethanol-water, from ethyl bromoacetate.

(viii) Using 5-acetamido-4-cyano-1 -(2,4, 6-trichlorophenyl)pyrazole (described in British Published Patent Specification No 2101999A): 5-(N-Acetyl-N-ethoxycarbonylmethyl)amino-4-cyano-1-(2,4,6-trichlorophenyl)pyrazole, m.p.

153-154-C, in the form of a pale yellow solid, after crystallisation from ethanol, from ethyl bromoacetate.

(ix) Using 5-tert-butoxycarbonylamino-4-cyano- 1 -(2,3,5, 6-tetrafluro-4-trifluoromethylphenyl)- pyrazole: 5-(N-tert-butoxycarbonyl-N-ethyl)amino-4-cyano- 1 -(2,3,5, 6-tetrafluoro-4trifluoromethylphenyl)- pyrazole, 110-112-C, in the form of colourless crystals, following chromatography using dichloromethane as eluent, from ethyl iodide.

By proceeding in a similar manner but carrying out the reaction in dimethylformamide in place of tetrahydrofuran and replacing the 4-cyano-5-methoxy-carbonylamino- 1 -(2, 3,4-trichlorophenyl)- pyrazole by the hereinafter appropriately substituted 5-acetamido-pyrazole and replacing the methyl iodide by the hereinafter indicated alkyl halide there was prepared: (x) Using 5-Acetamido-4-cyano-1 -(2-4-dichlorophenyl)pyrazole (described in British Published Patent Specification No 2101999A).

5-(N-Acetyl-N-iso-propyl)amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole, m.p. 149-150 C, in the form of colourless crystals, after crystallisation from ethanol, from iso-propyl iodide REFERENCE EXAMPLE 3 The hereinafter indicated compounds used as starting materials in Reference Examples 1 and 2 were prepared as follows: A stirred mixture of 4-cyano-5-di(phenoxycarbonyl)-amino-1-(2,3,4-trichlorophenyl)pyrazole (309) in methanol (600ml) was heated at reflux for 80 hours. After cooling the reaction mixture was evaporated and the residue was suspended in dichloromethane (250ml). The insoluble material was filtered off to give 4-cyano-5-methoxy-carbonylamino-1-(2,3,4-trichlorophenyl)pyra- zole (11 .5g), m.p. 205-207 C, in the form of a colourless solid.

The filtrate was passed through an aluminium oxide column (2009; May 8 Baker grade) using dichloromethane-methanol (20:1) as eluent. Evaporation of the eluate and crystallisation of the residue from a mixture of ethyl acetate and hexane gave a further quantity of 4-cyano-5 methoxycarbonylamino-1 -(2, 3,4-trichlorophenyl)pyrazole (4.69), m.p. 204-206 CC, in the form of a colourless solid.

By proceeding in a similar manner but replacing the 4-cyano-5-di-(phenoxycarbonyl)amino-1 (2,3,4-trichlorophenyl)pyrazole by 4-cyano-5-di(phenoxycarbonyl)amino- 1 -(2,3,5,6-tetrafluoro-4trifluoromethylphenyl)pyrazole (described in British Published Patent Application No 2101999A) and using tert-butanol in place of methanol, there was prepared: 5-tert-Butoxycarbonylamino-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, m.p. 154"C, in the form of colourless crystals, after crystallisation from a mixture of diethyl ether and hexane.

REFERENCE EXAMPLE 4 4-Cyano-5-di(phenoxycarbonyl)amino-1-(2,3,4-trichlorophenyl)pyrazole used as a starting material in Reference Example 3 was prepared as follows: Phenyl chloroformate (141g) was added to a stirred suspension of 5-amino-4-cyano-1-(2,3,4- trichlorophenyl)pyrazole (86.39; described in Published British Patent Specification 2,070,604A) in chloroform (600ml) at - 5CC to - 3 C. A solution of pyridine (71g) in chloroform (100ml) was added with stirring at 0 C to 5 C maintained by external cooling. The reaction mixture.was then stirred at laboratory temperature for 16 hours.The reaction mixture was then filtered and the solid product was washed with chloroform to give 4-cyano-5di(phenoxycarbonyl)-amino-1-(2,3,4-trichlorophenyl)pyrazole (135.6g), m.p. 205.5-206.5 C, in the form of a colourless solid.

REFERENCE EXAMPLE 5 5-Acetamido-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole used as a starting material in Reference Example 1 was prepared as follows: Bedistilled acetyl chloride (642ml) was added, over 15 minutes, to a stirred suspension of. 5 amino-4-cyano-1--(2,3,4-trichlorophenyl)pyrazole (11429; described in Published British Patent Specification 2,070,604A) in dry chloroform (4.8 1) at a temperatureof 16-20 C. The reaction mixture was cooled to 0 C and dry pyridine (640ml) was added over 20 minutes at a temperature of 0-5 C maintained by external cooling.After stirring the reaction mixture at room temperature overnight the solvent was removed under diminished pressure (temperature up to 40 C) and the solid residue was suspended in ethanol (3.5 1) and basified with aqueous ammonium (d: 0.880; 640ml). The basified solution was stirred and heated at reflux for 10 minutes, then cooled and stored at laboratory temperature overnight. The insoluble solid was filtered off and the filtrate was evaporated to dryness to give a solid residue. The solids were combined and were washed successively, using vigorous stirring, with water (3 1), hydrochloric acid (2N; 3 1) and water (3 X 3 I) and dried at 80 C to give 5-acetamido-4-cyano-1-(2,3,4- trichlorophenyl)pyrazole (12649), m.p. 222-223 C, in the form of an off-white solid.

EXAMPLE 31 Preparation of Compounds Nos 8, 66, 67, 68, 69, 9, 70, 71, and 22 A stirred mixture of 5-(4-chlorobutyramido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (2.39g) and dried potassium carbonate (2.429) in anhydrous acetone (55ml) was heated at reflux for 30 minutes. The reaction mixture was evaporated to dryness and water (40ml) and ethyl acetate (60ml) were added. The organic layer was separated, dried over an hydros sodium sulphate and was evaporated to give a colourless solid (29) which was crystallised from toluene to give 4cyano-5-(2-oxo-pyrrolidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole (1.259), m.p. 1 60-1 61 CC, in the form of colourless crystals.

By proceeding in a similar manner but replacing the 5-(4-chlorobutyramido-4-cyano-1-(2,3,4trichlorophenyl)pyrazole by the hereinafter indicated appropriately substituted phenylpyrazole, there were prepared: 4-Cyano-5-(4,4-dimethyl-2-oxo-azetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole, m.p.

39-141 CC, in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 60-80 C), following chromatography using dichloromethane as eluent, from 5-(3-chloro-3-methylbutyramido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole.

trans-4-Cyano-5-3,4-dimethyl-2-oxo-azetidin-1-yl)-1-(2,3,40trichlorophenyl)pyrazole m.p.

185-186 C, in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 60-80 C), following chromatography using dichloromethane as eluent, from (-I )-5-(3-chloro-2-methylbutyramido)-4-cyan 1-(2,3, 4-trichlorophenyl)pyrazole.

(i )-4-Cyano-5-(5-methyl-2-oxo-pyrrolidin- 1 -yl)- 1 -(2,3,4-trichlorophenyl)pyrazole, m. p.

135-150 C, in the form of colourless crystals, after crystallisation from diethyl ether, from (#)- 5-(4-chloropentanamido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole.

(i )-4-Cyano-5-(3-methyl-2-oxo-pyrrolidin-1 -yl)-1 -(2,3,4-trichlorophenyl)pyrazole, m. p.

123-1 24CC, in the form of colourless crystals, from (+ )-5-(4-chloro-2-methylbutyramido)-4- cyano-1 -(2,3,4-trichlorophenyl)pyrazole.

By proceeding in a similar manner but replacing the 5-(4-chlorobutyramido)-4-cyano-1-(2,3,4trichlorophenyl)pyrazole by the hereinafter indicated appropriately substituted phenylpyrazole and using potassium bicarbonate in place of potassium carbonate and using ethanol as solvent in place of acetone, there were prepared: ( ~ )-4-cyano-5-(4-ethyl-2-oxo-azetidin- 1 -yl)-1 -(2,3, 4-trichlorophenyl)pyrazole, m . p.

130-132 C, in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and petroleum ether (bp 40-60 C) [1:5], following chromatography using dichloromethane-ethyl acetate (98:2) as eluent from ( + )-5-(3-chloropentanamido-4-cyano-1-(2,3,4-trichloro- phenyl)pyrazole.

(+ )-4-cyano-5-(2-oxo-4-n-propylazetidin-1 -yl)- 1 -(2,3,4-trichlorophenyl)pyrazole, m. p.

1 24-125 CC, in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 60-80 C), following chromatography using dichloromethane as eluent, from (#)-4-cyano-5-(3-chlorohexanamido)-1-(2,3,4-trichlorophenyl)pyrazole.

( + )-4-cyano-5-(4-n-hexyl-2-oxo-azetidin- 1 -yl)- 1 -(2,3,4-trichlorophenyl)pyrazole, m. p.

122-133 C, in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 60-80 C), from ( + )-5-(3-chloronamido)-4-cyano-1-(2,3,4trichlorophenyl)pyrazole.

By proceeding in a similar manner but replacing the 5-(4-chlorobutyramido)-4-cyano-1-(2,3,4trichlorophenyl)pyrazole by (# )-5-(3-chloro-2-methylpropionamido)-4-cyano- 1 -(2,3,4-trichlorophenyl)pyrazole, there was prepared: (i )-4-cyano-5-(3-methyl-2-oxo-azetidin- 1 -yl)-1-(2,3,4-trichlorophenyl)pyrazole, m. p .

11 2-11 4CC, in the form of colourless crystals, after crystallisation from a mixture of ethylacetate and petroleum ether (bp 60-80 C).

EXAMPLE 32 Preparation of Compounds Nos 10 to 20, 72, 73, 74 and 21 A solution of 5-amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (11 .22g; described in Published British Patent Publication 2,070,604 A) and fi-chloropivaloyl chloride (12.169) in dry acetonitrile (60ml) was heated at reflux for 48 hours. The reaction mixture was evaporated to give a gum which was dissolved in acetone (100ml). Dried potassium carbonate (89) was added to a portion of the acetone solution (70ml) and the mixture was heated at reflux for 20 minutes.

The mixture was filtered and the solid was washed with acetone and the combined filtrates were evaporated to give a yellow oil (129). This oil was chromatographed using dichloromethane eluent. Evaporation of the eluate containing the major component gave 4-cyano-5-(3,3-dimethyl2-oxo-azetidin-yl)-1-(2,3,4-trichlorophenyl)pyrazole (1.1 g), m.p. 147-149 C, in the form of a colourless solid.

By proceeding in a similar manner but replacing the fi-chlorpivaloyl chloride by (#)-3- chlorobutyryl chloride and carrying out the cyclisation reaction in ethanol rather than acetone and isolating the lactam from the crude mixture of eliminated and cyclised product, there was prepared: (+ )-4-cyano-5-(4-methyI-2-oxo-azetidin-l -yl)-1 -(2,3,4-trichlorophenyl)pyrazole, m.p.

196-199 C, in the form of colourless crystals, after crystallisation from toluene, following chromatography using dichoromethane-ethyl acetate (99:1) as eluent.

By proceeding in a similar manner but replacing the ss-chloropivaloyl chloride by 3chloropropionyl chloride and carrying out the reaction in acetonitrile at a temperature of 3540CC, and isolating of the lactam from the crude mixture of eliminated and cyclised product there was prepared: 4-cyano-5-(2-oxo-azetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole, m.p. 1 62-1 65 C, in the form of a colourless solid, after crystallisation from toluene, following chromatography using dichloromethane as eluent.

By proceeding in a similar manner but replacing the ss-chloropivaloyl chloride by the hereinafter indicated acid chloride and replacing the 5-amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole by the hereinafter indicated appropriately substituted phenylpyrazole and isolating the lactam from the crude mixture of eliminated and cyclised product, there were prepared: 4-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(2-oxo-pyrrolidin-1-yl)pyrazole, m.p.

167-171 C, in the form of colourless plates, after crystallisation from a mixture of dioxan and petroleum ether (b.p. 40-60 C), from 4-chloro-butyryl chloride and 5-amino-4-cyano-1-(2,6dichloro-4-trifluoromethylphenyl)pyrazole.

(+ )-4-cyano-5-(4-methyl-2-oxo-azetid in- 1 -yl)- 1 -(2,4, 6-trichlorophenyl)pyrazole, m. p.

167-168 C, in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 40-60 C), following Soxhlet extraction of the crude product with petroleum ether (b.p. 40-60 C), from (j )-3-chlorobutyryl chloride and 5-amino-4-cyano-1- (2,4,6-trichlorophenyl)pyrazole (described in Published British Patent Specification 2,070,604 A).

(#)-4-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(4-methyl-2-oxo-azetidin-1-yl)pyrazole, m.p. 1 59-1 60CC, in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 40-60 C) (1:2), following extraction of an acetonitrile solution of the crude product with petroleum ether (b.p. 40-60'C) and chromatography of the petroleum ether extract using dichloromethane as eluent, from (#)-3-chlorobutyryl chloride and 5-amino-4cyano-1 -(2,6-dichloro-4-trifluoromethylphenyl)pyrazole.

(t )-1 2-Chlorn-4-methylphenyl)-4-cyano-5-(4-methyl-2-oxo-azetidin- 1 -yl)pyrazole, m. p.

130-1 31 CC, in the form of a colourless solid, after crystallisation from a mixture of toluene and diethyl ether, from (i )-3-chlorobutyryl chloride and 5-amino-1-(2-chloro-4-methylphenyl)-4- cyanopyrazole.

4-Cyano-5-(2-oxo-pyrrolidin-l -yl)- 1 -(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, m p.

91 -92CC, in the form of a colourless solid, after crystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 40-60 C), following chromatography using dichloromethane as eluent, from 4-chlorobutyryl chloride and 5-am ino-4-cyano- 1 -(2,3,5,6-tetrafluoro-4-trifluorome- thylphenyl)pyrazole.

( + )-4-Cyano-1 -(2,4-dichlorophenyl)-5-(4-methyl-2-oxo-azetidin- 1 -yl)pyrazole, m p.

140-142 C, in the form of a colourless solid, following Soxhlet extraction ofthe crude product with petroleum ether (b.p. 40-60 C), from (#)-3-chlorobutyryl chloride and 5-amino-4-cyano-1 (2,4-dichlorophenyl)pyrazole [described by P.L Southwick and B. Dhawan, J. Heter. Chem. 1-2.

1199-1205 (1975)].

( i )- 1 -(2-Chloro-4-isopropylphenyl)-4-cyano-5-(4-methyl-2-oxo-azetidin-1 -yl)pyrazole, m p.

125-128 C, in the form of a colourless solid, following chromatography using dichloromethane as eluent, from (#)-3-chlorobutyryl chloride and 5-amino-1-(2-chloro-4-isopropylphenyl)-4-cya nopyrazole (#)-1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-(3-methyl-2-oxo-azetidin-1-yl)pyrazole, m.p. 94-96 C, in the form of a colourless solid, following chromatography using dichlorometh ane as-eluent, from (i )-2-chlorobutyryl chloride and 5-amino-1-(2-chloro-4-trifluoromethylphe- nyl)-4-cyanopyrazole ( i )- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-(4-methyl-2-oxo-azetid in-i yl)pyrazole, m . p.

9294CC, in the form of a colourless solid, following chromatography using dichloromethane as - eluent, from (#)-3-chlorobutyryl chloride and 5-amino-l -(2-chloro-4-trifluoromethylphenyi)-4- cyanopyrazole.

(j )-4-Cyano-5-(4-methyI-2-oxo-azetidin-l -yl)-1-(2, 3,4, 6-tetrachlorophenyl)pyrazole, m.p.

187-191 C, in the form of colourless crystals, after crystallisation from a mixture of dichloro methane and petroleum ether (b.p. 60-80'C), the following chromatography using dichloro methane-ethyl acetate (9:1) as eluent, from (#)-3-chlorobutyryl chloride and 5-amino-4-cyano 1-(2,3,4,6-tetrachlorophenyl)pyrazole (described in British Published Patent Specification No 2101 999A).

(j )- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-(4-ethyl-2-oxo-azetidin- 1 -yl)pyrazole, m p.

74-76 C, in the form-of colourless crystals, following chromatography using dichloromethane as eluent, from (#)-3-chloropentanoyl chloride and 5-amino-1-(2-chloro-4-trifluoromethylphe nyl)-4cyanopyrazole-.. - 1 -(2-chloro-4-methylphenyl)-4-cyano-5-(2-oxo-pyrrolidin-1-yl)pyrazole, m.p.145-147 C, in the form of colourless crystals, after crystallisation from a mixture of ethanol and water, following extraction of the crude product with petroleum ether (b.p. 60-80 C), from 4-chlorobutyryl chloride and 5-amino-i -(2-chloro-4-methylphenyl)-4-cyanopyrazole.

(#)-4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl)-1-(2,3,4,6-tetrafluorophenyl)pyrazole, m.p.

141-143 C, in the form of a colourless solid, following chromatography using dichloromethane as eluent, from (#)-3-chlorobutyryl chloride and 5-amino-4-cyano-1-(2,3,4,6-tetrafluorophenyl) pyrazole (described in British Published Patent Specification No 2070604A).

(#)-1-(4-chloro-2,3,5,6-tetrafluorophenyl)-4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl)pyrazole, m.p. 145-147 C, in the form of a colourless solid, following chromatography using dichloro methane as eluent, from (#)-3-chlorobutyryl chloride and 5-amino-1-(4-chloro-2,3,5,6-tetrafluo- rophenyl)-4-cyanopyrazole (described in British Published Patent Specification No 2101999A).

By proceeding in a similar manner but replacing the ss-chloropivaloyl chloride by 4 chlorobutyryl chloride and 5-amino-4-cyano-1 -((2,3, 4-trichlorophenyl)pyrazole by 5-amino-1-(2- chloro-4-trifluoromethylphenyl)-4-cyanopyrazole and carrying out the reaction at reflux in toluene in place of acetonitrile, there was prepared: 1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-(2-oxo-pyrrolidin-1-yl)pyrazole, m.p.

106-110oC, in the form of a colourless solid, after crystallisation from a mixture of diethyl ether and petroleum ether (b.p. 40-60 C), following chromatography using diethyl ether-petroleum ether (b.p. 40-60 C) (2:1) as eluent.

EXAMPLE 33 Preparation of Compounds Nos 78 to 82 A solution of 5-(3-chloropropionamido)-4-cyano- 1 -(2, 6-dichloro-4-trifluoromethylphenyl)pyra zole (4.129) in a mixture of dimethylformamide (20ml) and dichloromethane (80ml) was added dropwise over 6 hours to a rapidly stirred suspension of powdered sodium hydride (0.309) in a mixture of dimethylformamide (20ml) and dichloromethane (80ml) at laboratory temperature.

The reaction mixture was then stirred for 24 hours. After standing at laboratory temperature for 48 hours, saturated aqueous ammonium chloride solution was added. The organic layer was removed, washed with water, dried over anhydrous magnesium sulphate and evaporated to dryness. The residue was chromatographed using diethyl ether-hexane (1:1) as eluent.

Evaporation of the eluate containing the faster moving component gave 4-cyano-1-(2,6-dichloro4-trifluoromethylphenyl)-5-(2-oxo-azetidin-1 -yl)pyrazole (1.409), m.p. 1 62-1 64CC, in the form of a colourless solid.

By proceeding in a similar manner but replacing the 5-(3-chloropropionamido)-4-cyano-1-(2,6dichloro-4-trifluoromethylphenyl)pyrazole by the hereinafter appropriately substituted phenylpyrazole there were prepared: 1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-(2-oxo-azetidin- 1 -yl)pyrazole, m . p. 168-16 9..CC, in the form of colourless crystals, after crystallisation from toluene, following chromatographyusing diethyl ether-hexane (1:1) as eluent, from 5-(3-chloropropionamido)-1 -(2-chloro-4-trifluo- romethylphenyl)-4-cyanopyrazole.

4-Cyano-5-(2-oxo-azetidin-1-yl)-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, m.p.

89-90 C, in the form of colourless crystals, following chromatography using diethyl etherhexane (1:1), from 5-(3-chloropropionamido)-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole.

4-Cyano-1 d4-ethyl-2,3,5,6-tetrafluorophenyl)-5-(2-oxo-azetidin-1 -yl)pyrazole, m p.

120.5-121.5iC, in the form of an off-white solid, following chromatography using dichloromethane-hexane (1:1) as eluent, from 5-(3chloropropionamido)-4-cyano-l -(4-ethyl-2,3,5,6-tet- rafluorophenyl)pyrazole.

(j )-4-Cyano 1 -(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-(3-methyl-2-oXo-azetidin-1 -yl)pyrazole, m.p. 111 -112.5iC, in the form of a pale pink solid, following chromatography using dichloromethane as eluent, from (# )-5-(3-chloro-2-methylpropionamido)-4-cyano-t-(4-ethyl- 2,3,5, 6-tetrafluorophenyl)pyrazole.

EXAMPLE 34 Preparation of Compounds Nos 83 to 89 Ethanethiol (0.429) was added over 20 minutes to a stirred suspension of N-chlorosuccinimide (0.919) in toluene (20ml) at a temperature of O4C to 5"C maintained by external cooling The reaction mixture was filtered to give a solution of ethanesulphenyl chloride.This filtrate was added dropwise with stirring to a solution of 5-amino-4-cyano-1 -(2,6-dichloro-4-trifluoromethyl phenyl)pyrazole sodium salt [prepared in situ by reaction of 5-amino-4-cyano-1-(2,6-dichloro-4trifluoromethylphenyl)pyrazole (1g) with sodium hydride (0.08g)] in tetrahydrofuran (20ml) containing 154rown-5 (2 drops) at a temperature of 0 C to 5CC. After 30 minutes, aqueous sodium bicarbonate solution (50ml) was added to the reaction mixture and the organic phase was washed with water and dried over anhydrous magnesium sulphate. Evaporation of the solvent gave a residue which was chromatographed using dichloromethane-ethyl acetate (20:1) as eluent.Evaporation of the eluate containing the major component gave a semi-solid (0.9g) which was crystallised from a mixture of ethyl acetate and hexane to give 4-cyano-1-(2,6 dichloro-4-trifluoromethylphenyl)-5-ethylthioaminopyrazole (0.79), m.p. 157-158'C, in the form of colourless crystals.

By proceeding in a similar manner but replacing the ethanethiol by the hereinafter indicated thiol and replacing the 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole by the hereinafter indicated appropriately substituted phenylpyrazole there were prepared:- 4-Cyano-5-iso-propylthioamino-1-(2,3,4-trichlorophenyl)pyrazole, m.p. 1 30-1 31 CC, in the form of a colourless solid, after crystallisation from a mixture of ethyl acetate and hexane, following chromatography using dichloromethane-ethyl acetate (20:1) as eluent, from 2propanethiol and 5-amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (described in British Published Patent Specification No 2070604A).

1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-iso-propylthioaminopyrazole, in the form of a viscous orange gum, following chromatography using dichloromethane-ethyl acetate (20:1) as eluent, from 2-propanethiol and 5-amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole.

1-(2-Chloro-4-trifloromethylphenyl)-4-cyano-5-n-propylthioaminopyrazole, in the form of an orange- gum, following chromatography using dichloromethane-ethyl acetate (20:1) as eluent, from 1 -propanethiol and 5-amino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-pyrazole.

5-n-Butylthioamino-1-(2-chloro-4-trifluoromethyl-phenyl)-4-cyanopyrazole, in the form of a viscous yellow gum, following chromatography using dichloromethane-ethyl acetate (20:1) as eluent, from 1-butanethiol and 5-amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole.

By proceeding in a similar manner carrying out the reaction without 15-Crown-5- and replacing the 5-amino- 1 -cyano- 1 -(2, 6-dichloro-4-trifluoromethylphenyl)pyrazole by the hereinafter indicated appropriately substituted phenylpyrazoles there were prepared: 4-Cyano-5-ethylthioamino-142,3,4-trichlorophenyl)pyrazole, m.p. 116-1 18CC, in the form of a colourless solid, after crystallisation from a mixture of ethyl acetate and hexane, following chromatography using dichloromethane-ethyl acetate (19:1) as eluent, from 5-amino-4-cyano-1.

(2,3,4-trichlorophenyl)pyrazole (described in British Published Patent Specification No 2070604A) 1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-ethyl-thioaminopyrazole, m. p. 90-91"C, after crystallisation from a mixture of diethylether and hexane, following chromatography using dichloromethane-ethyl acetate (20:1) as eluent, from 5-amino-1-(2-chloro-4-trifluoromethylphe- nyl)-4-cyanopyrazole.

EXAMPLE 35 Preparation of Compounds Nos 90 to 97 A mixture of 5-amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (10g) and ptoluenesulphonic acid hydrate (0.1g) in triethylorthoformate (40ml) was heated at reflux for 1 hour. After cooling, the reaction mixture was evaporated to dryness. The residue was dissolved in dichloromethane and saturated aqueous sodium bicarbonate solution was added. The organic phase was removed, dried over anhydrous magnesium sulphate and evaporated to give a colourless solid which was recrystallised from a mixture of ethyl acetate and hexane to give 4-cyano-5 ethoxymethyleneamino-1-(2,3,4-trichlorophenyl)pyrazole (11.0g), m.p. 131-1 32CC, in the form of colourless crystals.

By proceeding in a similar manner but replacing the 5-amino-4-cyano-1-(2,3,4-trichlorophe- nyl)pyrazole by the hereinafter appropriately substituted phenylpyrazole, there were prepared: 1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-ethoxymethyleneaminopyrazole, in the form of a viscous yellow gum, from 5-amino-I -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole.

4-Cyano-5-ethoxymethyleneamino-1 -(4-ethyl-2,3,5, 6-tetrafluorophenyl)pyrazole, in the form of a viscous orange gum, from 5-amino-4-cyano- 1 -(4-ethyl-2, 3,5, 6-tetrafluorophenyl)pyrazole (described in British Published Specificaton No 2101999A).

4-Cyano- 1 --(2, 6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethyleneaminopyrazole, m. p.

96-97"C, in the form of a pale yellow solid, after crystallisation from a mixture of ethanol and water, from 5-amino- 1 -(2, 6-dichloro-4-trifl uoromethylphenyl)-4-cyanopyrazole.

4-Cyano-5-ethoxymethyleneamino- 1 -(2,3,5, 6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, in the form of a viscous orange gum, following chromatography using dichloromethane-ethyl acetate (1 9:1) as eluent, from 5-amino-4-cyano- 1 -(2,3,5, 6-tetrafluoro-4-trifluoromethylphenyl)py- razole.

By proceeding in a similar manner but replacing the triethylorthoformate with the hereinafter indicated orthoesters there were prepared: 4-Cyano-5-methoxymethyleneamino-1-(2,3,4-trichlorophenyl)pyrazole, m. p. 158-160 C, in the form of greenish prisms, after crystallisation from a mixture of ethyl acetate and hexane, from trimethylorthoformate.

4-Cyano-5-(1-ethoxyethylidene)amino-1-(2,3,4-trichlorophenyl)pyrazole, m.p. 55-57'C, in the form of a colourless solid, after crystallisation from a mixture of ethyl acetate and hexane, following chromatography using dichloromethane-ethyl acetate (25:1) as eluent, from triethylorthoacetate.

4-Cyano-5-n-propoxymethyleneamino-1-(2,3,4-trichlorophenyl)pyrazole, m.p. 11 0-11 2 'C, in the form of a colourless solid, after crystallisation from a mixture of diethyl ether and hexane, from tri-n-propylorthoformate.

EXAMPLE 36 Preparation of Compounds Nos 3, 98, 102, 106, 109, 110 and 111 Sodium borohydride (0.229) was added to a stirred suspension of 4-cyano-5-(ethoxymethylene)amino-1-(2,3,4-trichlorophenyl)pyrazole (2.09; prepared as described in Example 35) in methanol (20ml). An exothermic reaction occurred then subsided after 10 minutes. The reaction mixture was then poured into water (50ml) and extracted with dichloromethane (3 x 25ml). The combined organic extracts were dried over anhydrous magnesium sulphate and evaporated to give a colourless semi-solid which was chromatographed using dichloromethane as eluent.

Evaporation of the eluent containing the faster moving component gave 4-cyano-5-methylamino-1-(2,3,4-trichlorophenyl)pyrazole (0.3g), m.p. 163-165"C, in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and hexane.

Evaporation of the eluent containing the slower moving component gave 4-cyano-5-methoxy methylamino-1-(2,3,4-trichlorophenyl)pyrazole (0.89), m.p. 129-130 C. in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and hexane.

By proceeding in a similar manner but replacing the 4-cyano-5-(ethoxymethylene)amino-1- (2,3,4-trichlorophenyl)pyrazole by the hereinafter indicated appropriately substituted phenyl pyrazole and carrying out the reduction using an excess of sodium borohydride there were prepared: 4-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylaminopyrazole, m. p. 165-167 C, in the form of colourless crystals, after crystallisation from a mixture ethanol and water, from 4cyano- 1 -(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethyleneaminopyrazole (prepared as described in Example 35).

1-(2-Chloro-4-ethylphenyl)-4-cyano-5-methylaminopyrazole, m.p.145-147eC, in the form of colourless crystals after crystallisation from a mixture of diethyl ether and hexane, following chromatography using dichloromethane-ethyl acetate (98:2) as eluent, from 1-(2-chloro-4ethylphenyl)-4-cyano-5-(ethoxymethylene)aminopyrazole (prepared as described hereinafter in Example 48).

4-Cyano-5-methylamino-1-(pentafluorophenyl)pyrazole, m.p. 113-1 14CC, in the form of colourless crystals, after crystallisation from a mixture of dichloromethane and petroleum ether (b.p.

60-80vC), and 4-cyano-5-methoxymethylamino-1 -(pentafluorphenyl)pyrazole, m .p. 145-147 CC, in the form of a colourless solid, after crystallisation from a mixture of dichloromethane and petroleum ether (b.p. 60-80 C), following chromatography using dichloromethane-ethyl acetate (98:2) as eluent, from 4-cyano-5-ethoxymethyleneamino-1 (pentafluorphenyl)pyrazole (prepared as described hereinafter in Example 48).

4-Cyano-1-(2,6-dibromo-4-trifluoromethylphenyl)pyrazole, m.p. 171-1 73CC, in the form of a colourless solid, after crystallisation from a mixture of ethyl acetate and hexane, from 4-cyano-1 - (2,6-dibromo-4-trifluoromethylphenyl)-5-ethoxymethyleneaminopyrazole (prepared as described hereinafter in Example 48).

EXAMPLE 37 (Preparation of Compound No 103) A mixture of 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(ethoxymethylene)aminopyra- zole- (2.59; described in Example 35) and dimethylamine (20ml) was heated at its reflux temperature for 3 hours. The reaction mixture was then evaporated under diminished pressure to give a gum which was chromatographed using dichloromethane as eluent. Evaporation of the eluent containing the major component gave a pale yellow solid (1.5g) which was crystallised from a mixture of diethyl ether and hexane to give, 4-cyano-1-(2,6-dichloro-4-trifluoromethylphe- nyl)-5-(di-ethylaminomethylene)aminopyrazole (1.5g), m.p. 90-91 CC, in the form of a yellow solid.

EXAMPLE 38 (Preparation of Compounds Nos 118, 119, 120 and 121) A solution of sodium methoxide in methanol [prepared by dissolving sodium (0.1 3g) in methanol (10ml)] was added to a solution of 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5- (2 < xo-azetidin-1-yl)pyrazole (1.889; prepared as described in Example 33) in methanol (15ml) under nitrogen. The reaction mixture was stirred at laboratory temperature for 30 minutes then acidified with 2N hydrochloric acid (5ml) and evaporated to dryness.The residue was dissolved in dichloromethane (50ml) and was washed with water (2 x 25ml), dried over anhydrous sodium sulphate and evaporated to give 4-cyano- 1 -(2, 6-dichloro-4-trifluoromethylphenyl)-5-(2- methoxycarbonylethyl)amino-pyrazole (1.939), m.p. 171-173"C, in the form of a colourless solid.

By proceeding in a similar manner but replacing the 4-cyano-1-(2,6-dichloro-4-trifluoromethyl phenyl)-5-(2-oxoazetidin-1-yl)pyrazole by the hereinafter indicated appropriately substituted 5lactam pyrazole and using the appropriate alkanol, there were prepared: 4-Cyano-5-(2-ethoxycarbonyl-1-methylethyl)amino-1-(2,3,4-trichlorophenyl)pyrazole, m.p.

92-93 C, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from ( + )-4Cyano-5-(4-methyl-2-oxo-azetidin-1 -yl)- 1 -(2, 3,4trichlorophenyl)- pyrazole (prepared as described in Example 32) and ethanol.

1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-(2-methoxycarbonylethyl)aminopyrazole, m @ p.

7880CC, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1), from 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-(2-oxo-azetidin-1-yl)pyrazole (prepared as described in Example 33) and methanol.

4-Cyano-5-(3-methoxycarbonylpropyl)amino-1-(2,3,4-trichloorophenyl)pyrazole, m.p.

108-111 CC, in the form of a colourless solid, following chromatography using dichloromethan ethyl acetate (20:1) as eluent, from 4-cyano-5-(2-oxo-pyrrolidin-1 -yl)-1 -(2,3,4-trichlorophenyl)- pyrazole (prepared as described in Example 31) and methanol.

EXAMPLE 39 (Preparation of Compound No 122) 4-Cyano-5-(2-oxo-azetidin-1-yl)-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole (1.0g@ prepared as described in Example 33) was dissolved in a solution of hydrogen chloride in ethanol (10ml) [prepared by dissolving gaseous hydrogen chloride (10g) in ethanol (50ml)]. The reaction mixture was heated at its reflux temperature for 1+ hours and after cooling was evaporated to dryness and the residue was chromatographed using dichloromethane-ethyl acetate (10:1) as eluent. Evaporation of the eluate containing the major component gave 4cyano-5-(2-ethoxycarbonylethyl)amino-1 -(2,3,5,6-tetrafluoro-4-trifiuoromethylphenyl)pyrazole (0.959), in the form of a pale yellow viscous oil.

EXAMPLE 40 (Preparation of Compounds Nos 123 to 126) A solution of 4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl)-1-(2,3,4-trichlorophenyl)jpyrazole (1.0g; prepared as described in Example 32) in di-n-butylamine (20ml) was heated under reflux for 3 > hours. The reaction mixture was evaporated to dryness and the residue chromatographed using dichloromethane-ethyl acetate (40:1) as eluent. Evaporation of the eluate containing the major component gave 4-cyano-5-[2-di-(n-butyl)aminocarbonyl- 1 methylethy9-amino- 1 -(2,3,4-trichloro- phenyl)pyrazole (0.95g), m.p. 101-103 C, in the form of a colourless solid.

By proceeding in a similar manner but replacing the 4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl) 1-(2,3,4-trichlorophenyl)pyrazole by the hereinafter indicated appropriately substituted 5-lactam phenylpyrazole, there were prepared: 4-Cyano-5-[2-(n-butyl)aminocarbonylethyl]amino- 1 -(2, 6-dichloro-4-trifluoromethyl phenyl)pyrazole, m.p. 174-176 C, in the form of a colourless solid, following chromatography using dichloromethane-ethyl acetate (1 5:1) as eluent, from 4-cyano-1-(2,6-dichloro-4-trifluoromethyl- phenyl)-5-(2-oxo-azetidin-1-yl)pyrazole (prepared as described in Example 33).

1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-(2-di-(n-butyl)aminocarbonylethyl]aminopyra- zole, m.p. 116-118 C, in the form of a colourless solid, following chromatography using dichloromethane-ethyl acetate (15:1) as eluent, from 1-(2-chloro-4Arifluoromethylphenyl)-4- cyano-5-(2-oxo-azetidin-1-yl)pyrazole (prepared as described in Example 33).

By proceeding in a similar manner but replacing the di-n-butylamine with the hereinafter indicated amine, there were prepared: 4-Cyano-5-[2-di-(n-propyl)aminocarbonyl- 1 -methyl-ethyl]amino- 1 -(2,3,4-trichlorophenyl)pyra- zole, m.p. 141-143 C, in the form of a colourless solid, following chromatography using dichloromethane-ethyl acetate (15:1) as eluent, from di-n-propylamine.

EXAMPLE 41 (Preparation of Compounds Nos 127 to 130) Sodium hydroxide (0.29) was added to a solution of 4-cyano-1-(4-ethyl-2,3,5,6-tetrafluoro- phenyl)-5-(3-methyl-2-oxo-azetidin-1-yl)pyrazole (0.709; prepared as described in Example 33) in aqueous ethanol (50ml; 90%). The reaction mixture was stirred at room temperature for 1 > hours then acidified with concentrated hydrochloric acid (8 ml) and extracted with dichloromethane (2 X 100ml).The combined organic extracts were washed with water (2 X 200 ml) dried over anhydrous magnesium sulphate and evaporated to give a yellow oil (0.79). This oil was chromatographed using dichloromethane-ethyl acetate (3:1). Evaporation of the eluate containing the faster moving component gave a yellow oil which was crystallised from a mixture of toluene and hexane to give 4-cyano-5-(2-ethoxycarbonylpropyl)amino- 1 -(4-ethyl-2,3,5,6-tetraflu- orophenyl)pyrazole (0.29), m.p. 76-78 C, in the form of colourless crystals.

Further elution of the column using dichloromethane-ethyl acetate-glacial acetic acid (15:5:2) gave a second compound. Evaporation of the eluate containing this slower component gave a colourless oil which was crystallised from a mixture of ethanol (4ml) and water (7ml) to give 5-(2-carboxypropyl)amino-4-cyano-1 -(4-ethyl-2, 3,5, 6-tetrafluorophenyl)pyrazole (O.lg), m p.

138.5-140 C, in the form of colourless crystals.

By proceeding in a similar manner but replacing the 4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-(3-methyl-2-oxo-azetidin-1-yl)pyrazole with the hereinafter indicated appropriately substituted phenyl pyrazole, there were prepared: 5-(2-carboxy- 1 -methylethyl)amino-4-cyano- 1 -(2,3,4-trichlorophenyl)pyrazole, m p.

192-1 94'C, in the form of colourless solid after crystaliisation from toluene, from 4-cyano-5-(4 methyl-2-oxo-azetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole (prepared as described in Example 32).

5-(2-Carboxyethyl)armino-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole, m.p.

153-155oC, in the form of a pale pink solid, after crystallisation from a mixture of ethanol and water, following chromatoraphy using dichloromethane-ethyl acetate (3:1) followed by ethyl acetate-glacial acetic acid (9:1) as eluent, from 4-cyano-1-(4-ethyl-2,3,5,6-tetrafluoro)-5-(2-oxo- azetidin-1-yl)pyrazole (prepared as described in Example 33).

EXAMPLE 42 (Preparation of Compounds Nos 75, 76 and 77) By proceeding as described in Example 32 for the preparation of 4-cyano-1-(2,6-dichloro-4- trifluoromethylphenyl)-5-(2-oxo-pyrrolidin-1-yl)pyrazole, there were prepared : (#)-1-(2-Chloro-4-methylphenyl)-4-cyano-5-(2-oxo-pyrrolidin-1-yl)pyrazole, m.p. 145-147 C, in the form of colourless crystals, after crystallisation from a mixture of ethanol and water, following extraction of the crude product with petroleum ether (b.p. 60-80 C) from 4chlorobutyryl chloride and 5-amino-1-(2-chloro-4-methylphenyl)-4-cyanopyrazole.

(i )-4-Cyano-5-(4-methyl-3-oxo-azetidin- 1 -yl)- 1 -(2,3,4,6-tetrafluorophenyl)pyrazole, m. p.

141-143 C, in the form of a colourless solid, following chromatography using dichloromethane as eluent, from ( + )-3-chlorobutyryl chloride and 5-amino-4-cyano-1-(2,3,4,6-tetrafluorophenyl)- pyrazoNe (prepared as described in British Published Patent Specification No 2070604A).

(#)-1-(4-Chloro-2,3,5,6-tetrafluorophenyl)-4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl)pyrazole, m.p. 145-147 C, in the form of a colourless solid, following chromatography using dichloromethane as eluent, from (+)-3-chlorobutyryl chloride and 5-amino-1-(4-chloro-2,3,5,6-tetrafluo- rophenyl)-4-cyanopyrazole (prepared as described in British Published Patent Specification No 2101999A).

EXAMPLE 43 (Prepara?ion of Compounds Nos 107 and 108) By proceeding as described in Example 25 for the preparation of 4-cyano-5-n-propylamino-1 (2,3,5,6--tetrafluoro-4-trifluoromethylphenyl)pyrazole but replacing the 5-amino-4-cyano-1- (2,3,5,6-tetrafluorophenyl)pyrazole by 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoro-methylphenyl)pyrazole there were prepared: 4-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-di-(n-propyl)aminopyrazole, m.p. 63-66 C, in the form of pale yellow crystals, after crystallisation from a mixture of ethanol and water, and 4-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-n-propylaminopyrazole, m.p. 143-145 C, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:2) as eluent.

EXAMPLE 44 (Preparation of, Compounds Nos 131 and 132) By proceeding as described in Example 26, there were prepared: 5-(2-Carboxyethyl)amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole, m.p. 25 227-228 C, in the form of a colourless solid, from 4-cyano-1 -(2,6-dichloro-4-trifluoromethyl- phenyl)-5-(2-methoxycarbonylethyl)amino-pyrazole (prepared as described in Example 38).

5-(2-Carboxyethyl)amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, m.p.

149-151 CC, in the form of colourless crystals, from 1-(2-chloro-4-trifluoro-methylphenyl)-4 cyano-1 -(2-methoxycarbonylethyl)amino-pyrazole, (prepared as described in Example 38).

EXAMPLE 45 (Preparation of Compound No 114) By proceeding as described in Example 27, but replacing the 5-(N-acetyl-N-ethoxycarbonylme thyl)amino-4-cyano-l -(2,3,4-trichlorophenyl)pyrazole by 5-(N-acetyl-N-ethoxycarbonylmethyl)am ino-142-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole (prepared as described in Reference Example 2), there was prepared: 1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-(2-hydroxyethyl)a minopyrazole, m p.

140-1 42CC, in the form of colourless crystals, after crystallisation from toluene.

EXAMPLE 46 (Preparation of Compounds Nos 115, 1 16, 117 and 133) By proceeding as described in Example 29(b), there was prepared: 1-(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-n-octyloxycarbonylmethylaminopyrazole, m.p.

62-64"C, in the form of colourless crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane as eluent, from n-octanol.

By proceeding as described in Example 29(c), there were prepared: 1 -(2-Chroro4-trifluoromethylphenyl)-4-cyano-5-iso-propylaminocarbonylmethylaminopyrazole, m.p. 1 62-1 63CC, in the form of fawn coloured crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane-ethyl acetate (3:1) as eluent, from iso-propylamine.

5-n-Butylaminocarbonylmethylamino- 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, m.p. 119-120 C, in the form of pale pink crystals, after crystallisation from a mixture of toluene and hexane, following chromatography using dichloromethane-ethyl acetate (3:1) as eluent, from n-butylamine.

By proceeding as described in Example 29(c), but using methoxyamine as the amine reactant and carrying out the reaction in diethyl ether in place of methyl ethyl ketone, there was prepared: 1 -(2-Chloro-4-trifluoromethylphenyl)-4-cyano-5-(methoxyaminocarbonylmethylam ino)pyrazole, m.p. 1 80-i 82'C, in the form of colourless crystals, after crystallisation from ethanol.

EXAMPLE 47 (Preparation of Compounds Nos 112 and 113) By proceeding as described in Example 30, but replacing the 5-(N-tert-butoxycarbonyl-N 3thyl!amino-4-c.yano-1 -(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole by the hereinafter in dicated appropriately substituted 1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazoles there were prepared: 4-Cyano-5-methylamino- 1 -(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, m , p.

171-1 73C, in the form of a colourless solid, after crystallisation from a mixture of diethyl ether and hexane, from 5-(N-tert-butoxy-carbonyl-N-methyl)amino-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifl- uoromethylphenyl)pyrazole.

4-Cyano-5-methoxycarbonyl methylamino- 1 -(2,3,5, 6-tetrafluoro-4-trifluoromethylphenyl)pyra zole, m.p. 92-94"C, in the form of a colourless solid, after crystallisafion from ethanol following chromatography using dichloromethane as eluent, from 5-(N-tert-butoxy-carbonyl-N-methoxycarbonylmethyl)amino-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole.

EXAMPLE 48 (Preparation of Compounds Nos 99 to 101, 104 and 105) By proceeding as described in Example 35, using the hereinafter indicated substituted phenyl pyrzoles, there were prepared: 4-Cyano-5-(ethoxymethylene)amino-1 -(2-nitro-4-trifluoromethylphenyl)pyrazole, m p.

93-95 C, in the form of a pale yellow solid after crystallisation from a mixture of ethanol and water, from 5-amino-4-cyano- 1 -(2-nitro-4-trifluoromethylphenyl)pyrazole (described by A.

Kreutzberger and K.- Burgwitz. J. Heteroyclic. Chem. 17 p 265 (1980)].

1 -(4-bromo-2, 3,5, 6-tetrafluorophenyl)-4-cyano-5-(ethoxymethylene)aminopyrazole, m @ p.

129-131 C, in the form of of colourless crystals, after crystallisation from a mixture of ethyl acetate and hexane, from 5-amino-1-(4-bromo-2,3,5,6-tetrafluorophenyl)pyrazole (described in British Published. Patent Specification No 2101 999A)..

4-Cyano-1-(2,6-dibromo-4-trifluoromethylphenyl)-5-(ethoxymethylene)aminopyrazole, m.p.

81-83"C, in the form of colourless crystals, after crystallisation from a mixture of diethyl ether and hexane, following chromatography using dichloromethane as eluent, from 5-amino-4-cyano1-(2,6-dibromo-4-trifluoromethylphenyl)pyrazole (described in British Published Patent Specification No 2101999A).

4-Cyano-5-(ethoxymethylene)amino-1-(pentafluorophenyl)pyrazole, in the form of an oil, from 5-amino-4-cyano-1-(pentafluorophenyl)pyrazole (described in British Published Patent Specification 2,070,604A).

1-(2-Chloro-4-ethylphenyl)-4-cyano-5-(ethoxymethylene)aminopyrazole, in the form of a colourless oil, following chromatography using dichloromethane as eluent, from 5-amino-1-(2-chloro-4ethylphenyl)-4-cyanopyrazole (described in British Published Patent Specification No 2101999A).

REFERENCE EXAMPLE 6 A mixture of 5-amino-4-cyano-1 -(2,3,4-trichlorophenyl)pyrazole (12.479) and 4-chlorobutyryl chloride (12.39) in dry acetonitrile (200ml) was stirred and gently warmed to effect dissolution.

The solution was cooled to room temperature and stirred, after 48 hours a further quantity of 4chlorobutyryl chloride (6.159) was added and stirring continued for 24 hours. The solution was evaporated under reduced pressure to give an oil which was chromatographed using dichloromethane-ethyl acetate (19:1) as eluent. Evaporation of the eluate containing the fastest moving component gave 5-(4-chlorobutyramido)-4-cyano- 1 -(2,3,4-trichlorophenyl)pyrazole (59), m p.

173-174"C, after crystallisation from toluene, in the form of pale yellow crystals.

By proceeding in a similar manner but replacing the 4-chlorobutyryl chloride by the hereinafter indicated acid chlorides, and effecting the reaction at the reflux temperature of the reaction medium, there were prepared: ( + )-5-(3-Chloropentanamido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, m.p. 1 28-1 31 CC after crystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 60-80 C) in the form of a colourless powder following chromatography using dichloromethane as eluent, from ( + )-3-chloropentanoyl chloride.

(f )-5-(3-Chloro-2-methylpropionamido)-4-cy 1 -(2,3,4-trichlorophenyl)pyrazole, m. p.

167-1 68 CC, in the form of a colourless powder following chromatography using dichloromethane-ethyl acetate (96:4) as eluent, from (i )-3-chloro-2-methylpropionylchloride.

(i )-4-Cyano-5-(3-chlorohexanamido)- 1 -(2,3,4-trichlorophenyl)pyrazole, m. p. 294-295 CC (with decomposition), in the form of a colourless solid, from (-c- )-3-chlorohexanoyl chloride.- 5-(3-Chloro-3-methylbutyramido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, in the form of a pale yellow oil, following chromatography using dichloromethane as eluent, from 3-chloro-3methylbutyryl chloride.

(-e )-5-(3-Chloro-2-methylbutyramido)-4-cyano- 1 -(2, 3,4-trichlorophenyl)pyrazole, m.p.

155-157 C, in the form of colourless crystals, after crystallisation from a mixture of ethyl acetate and petroleum ether (b.p. 60-80 C), following chromatography using dichloromethane as eluent, from (f )-3-chloro-2-methylbutyryl chloride.

(j )-5-(3-Chlorononamido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, in the form of a colour less solid following chromatography using dichioromethane as eluent, from (#)-3-chloronona- noyl chloride.

5-(4-Chloropentanamido)-4-cyano-1 -(2, 3,4-trichlorophenyl)pyrazole, m p. 1 26-1 27 CC, in the form of colourless crystals, after crystallisation from a mixture of diethyl ether and petroleum ether (b.p. 60-80 C), following chromatography using dichloromethane as eluent, from 4 chloropentanoyl chloride.

(#)-5-(4-Chloro-2-methylbutyramido)-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, in the form of a solid, from ( + )-4-chloro-2-methylbutyryl chloride.

By proceeding in a similar manner but replacing the 5-amino-4-cyano-1-(2,3,4-trichlorophe nyl)pyrazole by the hereinafter appropriately substituted pehnylpyrazole and the 4-chlorobutyryl chloride by the hereinafter indicated acid chlorides, there were prepared: 5-(3-Chloropropionamido)-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole, m.p.

180-181'C, in the form of colourless crystals, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenl)pyra- zole and 3-chloropropionyl chloride.

5-(3-Chloropropionamido)-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, in the form of a yellow glass, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5 amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole and 3-chloropropionyl chloride.

5-(3-Chloropropionamido)-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, m.p. 140-142 C, in the form of a colourless solid, after crystallisation from a mixture of toluene and hexane, from 5-amino-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyra zole and 3-chloropropionyl chloride.

5-(3-Chloropropionamido)-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole, m.p.

93.5-95.0 C, in the form of a colourless solid, following chromatography using diethyl ether-hexane (1:1) as eluent, from 5-amino-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyra zole (described in British Published Patent Specification No 2101999A) and 3-chloropropionyl chloride.

(#)-5-(3-Chloro-2-methylpropionamido)-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole, m.p. 119-121 C, in the form of a colourless solid after crystallisation from toluene, from 5 amino-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole and (#)-3-chloro-2-methylpropionyl chloride.

REFERENCE EXAMPLE 7 Phenyl-pyrazoles used as starting materials in Example 32 were prepared as follows: Ethoxymethylenemalononitrile C1.849; described by Huber, J. Amer. Chem. Soc., 65, 2224 (1943)] and 2,6-dichloro4-trifluoromethylphenylhydrazine (3.79) were added to a magnetically stirred solution of sodium acetate (0.6g) in glacial acetic acid (15ml) at laboratory temperature.

After stirring for 15 minutes, a colourless solid precipitated from the clear brown solution obtained and stirring was continued for a further 15 minutes. The mixture was then filtered. The solid obtained was washed successively with acetic acid, water, aqueous sodium bicarbonate solution and water, to give 2,6-dichloro-4-trifluoromethylphenylhydrazinomethylenemalononitrile (3.4g). m.p. 153-154 C, in the form of colourless crystals.

The 2,6-dichloro-4-trifluoromethylphenylhydrazinomethylenemalononitrile thus obtained was then heated at reflux for 45 minutes in ethoxyethanol (15ml). The hot solution was filtered and the filtrate was cooled, diluted with water (5ml), and filtered, to give 5-amino-4-cyano-1-(2,6 dichloro-4-trifluoromethylphenyl)pyrazole (2.5g), m.p. 165-167 C, in the form of off-white crystals.

By proceeding in a similar manner, but replacing the 2,6-dichloro-4-trifluoromethylphenylhy drazine by the hereinafter indicated appropriately substituted phenylhydrazine, there were prepared 5-Amino-i (2-chloro4-trifluornmethylphenyl)-4-cyanopyrazole, m p. 185-187 CC, after crystal lisation from toluene, in the form of fawn-coloured crystals, from 2-chloro-4-trifluoromethylphe nylhydrazine, via 2-chloro-4-trifluoromethylphenylhydrazinomethylenemalononitrile, in the form of a brown powder, m.p. 138-143 C.

5-Amino-4-cyano-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, m.p. 122-122.5 C, after crystallisation from toluene, in the form of off-white crystals, from 2,3,5,6-tetrafluoro-4 trifluoromethylphenylhydrazine (prepared as described by Alsop et al, J. Chem. Soc, 1962, 1801), via 2,3,5,6-tetrafluoro-4-trifluoro-methylphenylhydrazinomethylenemalononitrile, m.p.

90-93 C, in the form of a pale yellow solid.

5-Amino-1-(2-chloro-4-isopropylphenyl)-4-cyanopyrazole, m.p. 180.5-182 C, after crystallisa tion from toluene, in the form of fawn-coloured crystals, from 2-chloro-4-isopropylphenylhydra zine, via 2-chloro-4-isopropylphenylhydrazinomethylenemalononitrile.

5-Amino-1-(2-chloro-4-methylphenyl)-4-cyanopyrazole, m.p. 143-144 C, in the form of fawn coloured crystals, from 2-chloro-4-methylphenylhydrazine, m.p. 70-72 C [described by Bulow and Engler, Ber. 52, 639 (1 91 9)], via 2-chloro-4-methyphenylhydrazinomethylenemalononitrile (isolated in the form of a fawn-coloured solid, m.p. 1 33-1 34'C).

REFERENCE EXAMPLE 8 Phenylhydrazines used as starting materials in Reference Example 7 were prepared as follows: 2,6-Dichloro-4-trifluoromethylphenylaniline (4.3g) (described in United States Patent No 3,850,955) was dissolved, with stirring, in glacial acetic acid (23ml). A solution of sodium nitrite (1.5g) in concentrated sulphuric acid (11 ml) was then added at 55-60"C. The solution thus obtained was cooled to 0-5'C and a solution of stannous chloride (16.49) in concentrated hydrochloric acid (14ml) was added with vigorous stirring. A cream-coloured solid precipitated.

The mixture was filtered and the solid obtained was added to a mixture of aqueous ammonia solution and ice. The mixture thus obtained was extracted with diethyl ether (6 x 500ml) and the combined ethereal extracts were dried over sodium sulphate, filtered and evaporated to dryness to give 2,6-dichloro-4-trifluoromethylphenylhydrazine (3.7g), m.p. 54-56"C, in the form of a colourless crystalline solid.

By proceeding in a similar manner, but replacing the 2,6-dichloro-4-trifluoromethylaniline by 2-chloro-4-trifluoromethylaniline (described in United States Patent No 3,850,955), there was prepared: 2-Chloro-4-trifluoromethylphenylhydrazine, m.p. 38-39 C, in the form of a colourless solid.

REFERENCE EXAMPLE 9 2-Chloro-4-isopropylphenylhydrazine used as a starting material in Reference Example 7, was prepared as follows: A solution of 2-chloro-4-isopropylacetanilide (9.3g) in a mixture of glacial acetic acid (66ml) and hydrochloric acid (44my; density 1.1 9) was heated at reflux for 4 hours. After cooling, the reaction mixture was stirred and a solution of sodium nitrite (3.72g) in concentrated sulphuric acid (27ml) added at 15-20"C. The solution thus obtained was cooled to 0-5"C and a solution of stannous chloride (40g) in concentrated hydrochloric acid (35ml) was added with vigorous stirring. Acream-coloured precipitate formed. The mixture was filtered and the solid obtained basified with aqueous sodium hydroxide (2N, 350ml).This was extracted with dichloromethane (3 X 200ml) and the combined extracts washed with water (2 X 500ml), dried over anhydrous magnesium sulphate and evaporated to dryness to give 2-chloro-4-isopropylphenylhydrazine (4.59), m.p. 64-66"C, in the form of a colourless solid. The filtrate from the stannous-complex filtration was reduced under diminished pressure and the residue basified with aqueous sodium hydroxide (50% w/v), ice being added to maintain the temperature at 20-25'C. The mixture was similarly extracted with dichloromethane to furnish a further quantity of 2-chloro-4isopropylphenylhydrazine (3.03g), m.p. 65-67"C, in the form of a yellow solid.

REFERENCE EXAMPLE 10 Sulphuryl chloride (20ml) was added all at once to a magnetically-stirred solution of 4isopropylacetanilide [159; described by M.S. Carpenter et al, J. Org. Chem. 16, 586-617 (1 951)] in chloroform (100ml). When the resulting exothermic reaction had subsided (10 minutes) the reaction mixture was evaporated under diminished pressure to give a gum, which was chromatographed using dichloromethane as eluent. Evaporation of the eluate containing the major component gave a solid (14.319) which was triturated with cyclohexane to give 2-chloro4-isopropylacetanilide (10.86g), m.p. 109-110"C, in the form of an off-white solid.

REFERENCE EXAMPLE 11 By proceeding as described in Reference Example 2 (ix), there were prepared: 5-(N-tert-Butoxycarbonyl-N-methyl)amino-4-cyano 1 -(2,3,5, 6-tetrafluoro-4-trifluoromethylphe- nyl)pyrazole, m.p. 88-90"C, in the form of colourless crystals, following chromatography using diethyl ether-hexane (1:3) as eluent, from methyl iodide.

5-(N-Butoxycarbonyl-N-ethoxycarbonylmethyl)am i no-4-cyano- 1 -(2,3,5, 6-tetrafluoro-4-trifluoro- methylphenyl)pyrazole, m.p. 87-88'C, in the form of a colourless solid, after crystallisation from a mixture of diethyl ether and hexane, from ethyl bromoacetate.

The various Formulae referred to in the present specification are as follows:

B-NHNH2 IX

R5R6CO XXVI RyHCO XXVII

R6COX XXIX (R6Co)o XXX R7COX XXXI (R7CO)2O XXXII

B11OH xxxv R 2COX1 DVI

Claims

1. N-Phenylpyrazole derivatives of the general formula:

wherein A represents a group of the general formula:

wherein B1 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branchedchain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms, an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8 carbon atoms, and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyi groups, may be the same of different, an alkoxyaminocarbonyl group, wherein the alkoxy moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, an alkanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branchedchain, a -C( = OH)Het group, wherein Het represents a saturated, nitrogen-containing heterocyclic group having from 3 to 7 atoms in the ring including up to two additional heteroatoms selected from oxygen, nitrogen and sulphur, and linked to the -C( = 0)- group of the group = = O)Het by the nitrogen atom, or one or more halogen atoms, or R' represents a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms, an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8 carbon atoms and which, when the amino-carbonyl group is substituted by two alkenyl or alkynyl groups, may be the same or different, an alkoxyaminocarbonyl group wherein the alkoxy moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, an alkane-sulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 8 carbon atoms, and may be straight- or branched-chain, a -C( = O)Het group, wherein Het represents a saturated, nitrogen-containing heterocyclic group having from 3 to 7 atoms in the ring including up to two additional hetero-atoms selected from oxygen, nitrogen and sulphur, and linked to the -C( = 0)- group of the group -C( = O)Het by the nitrogen atom, or one or more halogen atoms, or B1 represents a cycloalkyl group containing from 3 to 6 carbon atoms unsubstituted or substituted by one or more straight- or branchedchain alkyl groups containing from 1 to 4 carbon atoms, and R2 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms, an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups, may be the same or different, an alkoxyaminocarbonyl group wherein the alkoxy moiety contains from 1, to 8 carbon atoms and may be straightor branched-chain, an alkanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, a -C( = O)-Het group, wherein Het represents a saturated nitrogen-containing heterocyclic group having from 3 to 7 atoms in the ring including up to two additional heteroatoms selected from oxygen, nitrogen and sulphur, and linked to the -C( = 0)- group of the group -C( = O)-Het by the nitrogen atom, or one or more halogen atoms, or R2 represents a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms, an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups may be the same or different, an alkoxyaminocarbonyl group wherein the alkoxy moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, an alkanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, a -C( = O)Het group, wherein Het represents a saturated, nitrogen-containing heterocyclic group having from 3 to 7 atoms in the ring including up to two additional hetero atoms selected from oxygen, nitrogen and sulphur, and linked to the = = O)Het by the nitrogen atom, or one or more halogen atoms, or R2 represents a cycloalkyl group containing from3 to 6 carbon atoms unsubstituted or substituted by one or more straightor branched-chain alkyl groups containing from 1 to 4 carbon atoms, or R1 represents an alkylthio group wherein the alkyl moiety contains from 1 to 4 carbons atoms and may be straight- or branched-chain and R2 represents a hydrogen atom, or A represents a group of the general formula:

wherein RP represents a straight- or branched-chain alkoxy group containing from 1 to carbon atoms or an amino group substituted by one or two straight- or branched-chain alkyl groups each containing from 1 to 4 carbon atoms, which, when the amino group is substituted by two alkyl groups, may be the same or different, and R9 represents a hydrogen atom or a straight- or branched-chain alkyl containing from 1 to 4 carbon atoms, or A represents a group of the general formula::

wherein R", Rb, RC, Rd, Re and Rt, which maybe the sane or different, each represents a hydrogen atom or a straight- or branched-chain akyl group containing from 1 to 6 carbon atoms and m represents 0, 1 or 2, and wherein, when m represents 1 or 2, R" and Rb of the portions of the group of general formula IV represented by the general formula:

may be the same or different, and B represents a group of general formula::

wherein R9 represents a fluorine, chlorine or bromine atom, a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms unsubstituted or substituted by one or more halogen atoms or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 4 carbon atoms, Rh represents a fluorine, chlorine or bromine atom or a nitro, methyl or ethyl group and Ri, Rk and Rn, which may be the same or different, each represents a hydrogen, fluorine, chlorine, or bromine atom or a nitro, methyl or ethyl group or Rh and Ri each represent a chlorine atom and Rg, Rk and Rn each represent a hydrogen atom, and when R' and/or R2 represents an alkyl, alkenyl or alkynyl group substituted by a carboxy group, salts thereof with agriculturally acceptable acids.

2. N-Phenylpyrazole derivatives of the general formula ll depicted in claim 1, wherein A represents a group of the general formula Ill depicted in claim 1 wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms subsubstituted or substituted by a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 5 carbon atoms or one or more halogen atoms, or R' represents a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms unsubstituted or substituted by a straight-or branched-chain alkoxy group containing from 1 to 4 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 5 carbon atoms or one or more halogen atoms, or R' represents a cycloalkyl group containing from 3 to 6 carbon atoms unsubstituted or substituted by one or more straight- or branched-chain alkyl groups containing from 1 to 4 carbon atoms and R2 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms unsubstituted or substituted by a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 5 carbon atoms or one or more halogen atoms, or R2 represents a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms unsubstituted or substituted by a straightor brached-chain alkoxy group containing from 1 to 4 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 5 carbon atoms or one or more halogen atoms, or R2 represents a cycloalkyl group containing from 3 to 6 carbon atoms unsubstituted or substituted by one or more straight- or branched-chain alkyl groups containing from 1 to 4 carbon atoms, groups represented by R' and R2 being the same or different, or A represents a group of the general formula IV depicted in claim 1, wherein R", Rb, RC, Rd, Be and Rf, which may be the same or different, each represent a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms and m represents 0, 1 or 2 and wherein, when m represents 1 or 2, R" and Rb of the portions of the group of general formula IV represented by the general formulae VI and VII depicted in claim 1 may be the same or different, and B represents a group of the general formula V depicted in claim 1, wherein Rs represents a fluorine, chlorine or bromine atom, a straight- or branched-chain akyl group containing from 1 to 4 carbon atoms, a trifluoromethyl group or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 4 carbon atoms, Rh represents a fluorine, chlorine or bromine atom or a nitro, methyl or ethyl group and Ri, Rk and Rn, which may be the same or different, each represent a hydrogen, fluorine, chlorine or bromine atom or a nitro, methyl or ethyl group, or Rh and Ri each represents a chlorine atom and R9, Rk and R" each represent a hydrogen atom, and, when R' and/or R2 represent an alkyl, alkenyl or alkynyl group substituted by a carboxy group, salts thereof with agriculturally acceptable bases.

3. N-Phenylpyrazole derivatives according to claim 1 wherein B in general formula II depicted in claim 1 is as defined in claim 1 and A in general formula II depicted in claim 1 represents a group of general formula Ill depicted in claim 1, wherein R' represents a straight-or branched-chain alkyl group containing from 1 to 4 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 7 carbon atoms, an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 4 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 4 carbon atoms and which, when the amino-carbonyl group is substituted by two alkenyl or alkynyl groups may be the same or different, an alkoxyaminocarbonyl group wherein the alkoxy moiety contains from 1 to 4 carbon atoms and may be straight- or branchedchain, an alkane-sulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain, a -C( = O)-Het group wherein Het represents morpholino, or one or more chlorine atoms, or R' represents a straight- or branchedchain alkenyl or alkynyl group containing from 2 to 4 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 7 carbon atoms, an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 4 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 4 carbon atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups may be the same or different, an alkoxyaminocarbonyl group wherein the alkoxy moiety contains from 1 to 4 carbon atoms and may be straight- or branchedchain, an alkanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain, a -C( = O)-Het group wherein Het represents morpholino, or one or more chlorine atoms, or Rl represents a cycloalkyl group containing from 3 to 6 carbon atoms unsubstituted or substituted by one or more methyl or ethyl groups, and R2 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 7 carbon atoms, an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 4 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 4 carbon atoms and which, when the amino-carbonyl group is substituted by two alkenyl or alkynyl groups may be the same or different, an alkoxyaminocarbonyl group wherein the alkoxy moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain, an aikanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain, a -C( = O)-Het group wherein Het represents morpholino, or one or more chlorine atoms, or R2 represents a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 4 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 7 carbon atoms, an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 4 carbon atoms, and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 4 carbons atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups may be the same or different, an alkoxy-aminocarbonyl group wherein the alkoxy moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain, an alkanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain, a -C( = O)-Het group wherein Het represents morpholino, or one or more chlorine atoms, or R2 represents a cycloalkyl group containing from 3 to 6 carbon atoms unsubstituted or substituted by one or more methyl or ethyl groups, groups represented by R1 and R2 being the same or different, or R' represents an alkylthio group wherein the alkyl moiety contains from 1 to 4 carbon atoms and may be straight- or branchedchain and R2 represents a hydrogen atom, or A represents a group of the general formula IIIA depicted in claim 1, wherein RP represents a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms or an amino group substituted by one or two straight- or branchedchain alkyl groups each containing from 1 to 4 carbon atoms, and which, when the amino group is substituted by two alkyl groups may be the same or different, and Rq represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, or A represents a group of the general formula IV depicted in claim 1, wherein R", Rb, BC, Rd, Re and Rf, which may be the same or different, each represent a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms and m represents 0, 1 or 2.

4. N-Phenylpyrazole derivatives according to claim 1, wherein A represents a group of general formula Ill depicted in claim 1, wherein R1 represents a straight- or branched-chain alkyl group containing froml to 8 carbon atoms unsubstituted or substituted as defined in claim 1.

5. N-Phenylpyrazole derivatives according to claim 1 wherein A represents a group of general formula Ill depicted in claim 1, wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms unsubstituted or substituted as defined in claim 2.

6. N-Phenylpyrazole derivatives according to claim 1 wherein A represents a group of general formula Ill depicted in claim 1, wherein R' represents a methyl, ethyl, 1-methylethyl or propyl group substituted as defined in claim 1.

7. N-Phenylpyrazole derivatives according to claim 1 wherein A represents a group of general formula Ill depicted in claim 1, wherein R' represents a methyl, ethyl, 1-methylethyl or propyl group substituted as defined in claim 3.

8. N-Phenylpyrazole derivatives according to claim 1, wherein A represents a group of general formula Ill depicted in claim 1 wherein R' represents a methyl group substituted as defined in claim 1.

9. N-Phenylpyrazole derivatives according to claim 1 wherein A represents a group of general formula Ill depicted in claim 1 wherein B1 represents a methyl group substituted as defined in claim 3.

10. N-Phenylpyrazole derivatives according to claim 1 wherein A represents a group of general formula Ill depicted in claim 1 wherein R1 represents a methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl, ethoxycarbonyl-methyl, n-propoxycarbonylmethyl, iso-propoxycarbonylmethyl, n-butoxycarbonylme- thyl, n-pentyloxycarbonylmethyl, n-hexyloxycarbonylmethyl, carboxymethyl, carbamylmethyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, diethyl-aminocarbonylmethyl, methoxymethyl, 2-methoxycarbonylethy, 2-ethoxycarbonyl- 1 -methylethyl, 2 methoxycarbonylethyl, 3-methoxycarbonylpropyl, 2-ethoxycarbonylethyl, 2-di-(n-butyl)aminocarbonyl 1 -methylethyl, 2-di-(n-propyl)aminocarbonyl- 1 -methylethyl, 2-ethoxycarbonylpropyl, 2-carboxypropyl, 2-carboxy- 1 -methylethyl, 2-carboxyethyl, methoxyaminocarbonylmethyl, morpholin4-ylcarbonylmethyl, 2-chloroethyl or 2-hydroxyethyl group and R2 represents a hydrogen atom or a methyl or n-propyl group.

11. N-Phenylpyrazole derivatives according to claim 10 wherein R2 represents a hydrogen atom.

1 2. N-Phenylpyrazole derivatives according to claim 1 wherein A represents a group of general formula Ill depicted in claim 1 wherein B1 represents an ethylthio, n-propylthio, isopropylthio or n-butylthio group and R2 represents a hydrogen atom.

13. N-Phenylpyrazole derivatives according to claim 1 wherein A represents a group of general formula IIIA depicted in claim 1 wherein RP represents a methoxy, ethoxy, n-propoxy or diethylamino group and R9 represents a hydrogen atom or a methyl group.

14. N-Phenylpyrazole derivatives according to claim 13 wherein A represents a group of general formula IIIA depicted in claim 1 which is methoxymethyleneamino, ethoxymethyleneamino, n-propoxymethyleneamino, ethoxyethylideneamino or diethylaminomethyleneamino.

15. N-Phenylpyrazolederivatives according to claim 1 wherein A represents a 2-oxo-azetidin 1 -yl, 3-methyl-2-oxo-azetidin-l -yl, 4-methyl-2-oxo-azetidi n- 1 -yl, 4-ethyl-2-oxo-azetidin- 1 -yl, 2-oxo 4-n-propyl-azetid in- 1 -yl, 3, 3-dimethyl-2-oxo-azetidin-l -yl, 3,4-dimethyl-2-oxo-azetidin-l -yl, 4,4dimethyl-2-oxo-azetidin- 1 -yl, 4-n-hexyl-2-oxo-azetidin- 1 -yl, 2-oxo-pyrrolidin-1- -yl, 3-methyl-2-oxo pyrrolidin- I -yl or 5-methyl-2-oxo-pyrrolidin-1 -yl group.

16. N-Phenylpyrazole derivatives according to any one of claims 1 to 15 wherein in B in general formula Il depicted in claim 1, R9 represents a fluorine, chlorine, or bromine atom, a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms or a trifluoromethyl group, Rh represents a fluorine, chlorine or bromine atom or a nitro group, R represents a hydrogen, fluorine or chlorine atom, Rk represents a hydrogen or fluorine atom and R" represents a hydrogen, fluorine, chlorine or bromine atom.

1.7. . N-Phenylpyrazole derivatives according to claim 16 wherein R9 represents a fluorine or chlorine atom or a methyl, ethyl, iso-propyl or trifluoromethyl group.

18. N-Phenylpyrazole derivatives according to any one of claims 1 to 16 wherein B in general formula ll depicted in claim 1 represents a 2, 3, 4-trichlorophenyl, 2-chloro-4trifluoromethylphenyl, 2,6-dichloro-4-trifluoromethylphenyl, 2,4, 6-trichlorophenyl, 2-chloro-4methylphenyl, 2,3, 5,6-tetrafluoro-4-trifluoromethylphenyl, 24-dichlorophenyl, 2-chloro-4-iso- propylphenyl, 4-ethyl-2, 3, 5,6-tetrafluorophenyl, 2,3,4,6-tetrachlorophenyl, 4-chloro-2,3,5,6-tetrafluorophenyl, 2-nitro-4-trifluoromethylphenyl, 4-bromo-2,3,5,6-tetrafluorophenyl, 2,6-dibromo4-trifluoromethylphenyl, pentafluorophenyl, 2-chloro-4-ethylphenyl or 2,3,4,6-tetrafluorophenyl group. -

19.N-Phenylpyrazole derivatives according to any one of claims 1 to 16 wherein B in general formula Il depicted in claim 1 represents a 2,3,4-trichlorophenyl or 2-chloro-4trifluoromethylphenyl group.

20. 4-Cyano-5-ethylamino-1-(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-n-propylamino-1 (2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-methylamio-1(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-(prop-2-enyl)amino- 1 -(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-(prop-2-ynyl)amino- 1 (2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-isopropylamino-1-(2,3,4-trichlorophenyl)pyrazole and 5-n-,butylamino-4cyano-1 -(2,3,4-trichlorophenyl)pyrazole.

21. 4-Cyano-5-(2-oxo-pyrrolidin-i -yl)- 1 -(2,3, 4-trichlorophenyl)pyrazole, 4-cyano-5-(4-ethyl-2 oxo-azetidin- 1 -yl)- 1 -(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-(3,3-dimethyl-2-oxo-azetidin-1- -yl)1-(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-(4-methyl-2-oxd-azetidi 1 -yl)-1 -(2, 3,4-trichlorophenyl)pyrazole, 4-cyano-5-(2-oxo-azetidin-l -yl)- 1 -(2,3 ,4-trichlorophenyl)pyrazole, 4-cyano- 1 -(2,6-d i- chloro-4-trifluoromethylphenyl)-5-(2-oxo-pyrrolidin-1-yl)pyrazole, 4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl)-1-(2,4,6-trichlorophenyl)pyrazole, 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(4methyl-2-oxo-azetidin- 1 -yl)pyrazole, 1 -(2-chloro-4-methyl phenyl)-4-cyano-5-(4-methyl-2-oxo-azeti- din-i -yl)-pyrazole, 4-cyano-5-(2-oxo-pyrrolidin- 1 -yl)- 1 -(2,3,5,6-tetrafluoro-4-trifluoromethyl phe- nyl)pyrazole, 4-cyano- 1 -(2,4-dichlorophenyl)-5-(4-methyl-2-oxo-azetidin- 1 -yl)pyrazole, 1 -(2-chloro4-isopropylphenyl)-4-cyano-5-4-methyl-2-oxo-azetidin-1-yl)pyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-(3-methyl-2-oxo-azetidin- 1 -yl)pyrazole, 1 -(2-chloro-4-trifl uoromethylphenyl)-4- cyano-5-(2-oxo-pyrrolidin- 1 -yl)pyrazole and 4-cyano-5-(3-methyl-2-oxo-azetidin- 1 -yl)- 1 -(2,3,4-tri- chlorophenyl)pyrazole.

22. 5-iso-Butylamino-4-cyano- 1 -(2,3,4-trichlorophenyl)pyrazole, 5-sec-butylamino-4cyano- 1 (2,3,4-trichlorophenyl)pyrazole, 5-sec-butylamino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopy- razole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-iso-propylaminopyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-methylaminopyrazole, 5-n-butylamino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, 5-iso-butylamino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-n-jpropylaminopyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-ethylaminopyrazole, 4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-methylaminopyrazole, 4cyano-5-ethylamino- 1 -(4-ethyl-2, 3,5, 6-tetrafluorophenyl)pyrazole, 4-cyano1 -(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-n-propylaminopyrazole, 4 cyano -(2,4-dichlorophenyl)-5n-propylaminopyrazole, 4-cyano-1 (2,4-dichlorophenyl)-5-methylaminopyrazole, 4-cyano-1 -(2,4- dichlorophenyl)-5-iso-propylaminopyrazole, 4-cyano-1-(2,4-dichlorophenyl)-5-ethylaminopyrazole, 4-cyano-5-di(n-propyl)amino-1-(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-dimethylamino-1 - (2, 3,4-trichlorophenyl)pyrazole, 4-cyano-5-ethoxycarbonylmethylamino-l -(2, 3,4-trichlorophenyl)pyrazole, 4-cyano-5-n-propylamino-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, 5-carboxymethylamino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole, 5-carboxymethylamino-1-(2-chloro4-trifluoromethylphenyl)-4-cyanopyrazole, 5-carboxymethylamino-4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)pyrazole, 5-carboxymethylam ino-4-cyano- 1 -(2,4,6-trichlorophenyl)pyrazole, 4-cy ano-5-(2-hydroxyethyl)amino-1-(2,3,4-trichlorophenyl)pyrazole, 5-(2-chloroethylamino)-4-cyano-12,3,4-trichlorophenyl)pyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-ethoxycarbonylmethylaminopyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-methoxycarbonylmethylaminopyrazole, 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-n-propoxycarbonyl methyla mi nopyrazole, 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-iso-propoxycarbonyl methylami nopyrazole, 5-n-butoxycarbonylmethyl-amino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, 1-(2-chloro-4trifluoromethylphenyl)-4-cyano-5-n-pentyloxycarbonylmethylaminopyrazole, 1-(2-chloro-4-trifluo romethyl phenyl)-4-cyano-5-n-hexyloxycarbonylmethylaminopyrazole, 1-(2-chloro-4-trifluorome- thylphenyl)-4-cyano- 5-ethylaminocarbonylmethylami nopyrazole, 5-carbamylmethylamino- 1 -(2chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5methylaminocarbonylmethylaminopyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-n-pro- pylaminocarbonylmethylaminopyrazole, 1 -(2-chlorn-4-trifluornmethylphenyl)-4-cyano-5-diethyl aminocarbonylmethylaminopyrazole, 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-n-pentylami nocarbonylmethylaminopyrazole, 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-n-hexylaminocar- bonylmethylaminopyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-n-octylaminocarbonylmethylaminopyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-(morpholin-4-ylcarbonylmethyl)aminopyrazole, 4-cyano-5-ethylamino-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, 4-cyano-5-(methoxymethyl)amino-1-(2,3,4-trichlorophenyl)pyrazole, 4-cyano-1-(2,6-dichloro-4trifluoromethylphenyl)-5-methylaminopyrazole, 1-(2-chloro-4-ethylphenyl)-4-cyano-5-methylaminopyrazole, 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-n-propylaminopyrazole, 4-cyano1-(2,6-dichloro-4-trifluoromethylphenyl)-5-di(n-propyl)aminopyrazole, 4-cyano-5-methoxymethyl amino-l -pentafluorophenylpyrazole, 4-cyano-1-(2,6-dibromo-4-trifluoromethylphenyl)-5-methylaminopyrazole, 4-cyano-5-methylamino-1-pentafluorophenylpyrazole, 4-cyano-5-methylamino-1 (2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, 4-cyano-5-methoxycarbonylmethylamino-1 (2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-(2-hydroxyethyl)aminopyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-n-octyloxy carbonylmethylaminopyrazole, 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-isopropylaminocarbonylmethylaminopyrazole, 5-n-butylamino-carbonylmethylamino-1-(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(2-methoxycarbonylethyl)aminopyrazole, 4-cyano-5-(2-ethoxycarbonyl-1-methylethyl)amino-1-(2,3,4-trichlorophenyl)pyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-(2-methoxycarbonylethyl)aminopyrazole, 4-cyano-5-(3-methoxycarbonylpropyl)amino-1-(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-(2 ethoxycarbonylethyl)amino 1(2,3,5, -(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole, 4-cyano-5-[2- di-(n-butyl)aminocarbonyl- 1 -methylethyl]amino- 1 -(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-[2di-(n-butyl)aminocarbonylethyl]amino-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole, 1-(2 chloro-4-trifluorom ethylphenyl)-4-cyano-5-(2-di-(n-butyl)ami nocarbonylethylam i nopyrazole, 4-cyano-5-[2-(di-(n-propyl)aminocarbonyl-1-methylethyl]-amino-1(2,3,4-trichlorophenyl)pyrazole, 4cyano-5-(2-ethoxycarbonylpropyl)amino-1-(4-ethyl)-2,3,5,6-tetrafluorophenyl)pyrazole, 5-(2-carboxypropyl)amino-4-cyano- 1 -(4-ethyl- 2,3,5,6 -tetrafluorophenyl)pyrazole, 5-(2-carboxy- 1 -methyle thyl)amino-4-cyano-l -(2, 3,4-trichlorophenyl)pyrazole, 5-(2-carboxyethyl)amino-4-cyano-l -(4- ethyl-2,3,5,6-tetrafluorophenyl)pyrazole, 5-(2-carboxyethyl)amino-4-cyano- 1 -(2,6-dichloro-4-trifl - uoromethylphenyl)pyrazole, 5-(2-carboxyethyl)-am ino- 1 -(2-ch loro-4-trifl uoromethyl phenyl)-4-cyano-pyrazole and 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-(methoxyaminocarbonylmethy- lamino)pyrazole.

23. 4-Cyano-5-(4,4-dimethyl-2-oxo-azetidin- 1 -yI)- 1 -(2, 3,4-trichlorophenyl)pyrazole, 4-cyano 5-(3, 4-dimethyl-2-oxo-azetidin- 1 -yl)- 1 -(2, 3,4-trichlorophenyl)pyrazole, 4-cyano-5-(5-methyl-2-oxopyrrolidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-(3-methyl-2-oxo-pyrrolidin-1-yl)-1 (2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-(2-oxo-n-propylazetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-(4-n-hexyl-2-oxo-azetidin-1-yl)-1-(2,3,4-trichlorophenyl)pyrazole, 1-(2-chloro4-trifluoromethylphenyl)-4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl)pyrazole, 4-cyano-5-(4-methyl-2oxo-azetidin-1-yl)-1-(2,3,4,6-trichlorophenyl)pyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-(4-ethyl-2-oxo-azetidin-1-yl)pyrazole, 1-(2-chloro-4-methylphenyl)-4-cyano-5-(2-oxo-pyrrolidin-1-yl)pyrazole, 4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl)-1-(2,3,4,6-tetrafluorophenyl)pyrazole, 1-(4-chloro-2,3,5,6-tetrafluorophenyl)-4-cyano-5-(4-methyl-2-oxo-azetidin-1-yl)pyrazole, 4-cyano1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(2-oxo-azetidin-1-yl)pyrazole, 1-(2-chloro-4-trifluorome thylphenyl)-4-cyano-5-(2-oxo-azetidin-l -yl)pyrazole, 4-cyano-5-(2-oxo-azetidin-1-yl)-1-(2,3,5,6 -(2,3,5,6-tet- rafluoro-4-trifluoromethylphenyl)pyrazole, 4-cyano-1-(4-ethyl-2,3,5,6-tetrafluorophenyl)-5-(2-oxo azetidin-1 -yl)pyrazole and 4-cyano-1-(4-ethyl- 2,3,5,6-tetrafluorophenyl)-5-(3-methyl-2-oxo-azeti- din-i -yl)pyrazole.

24. 4-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethylthioaminopyrazole, 4-cyano-5isopropylthioamino-1-(2,3,4-trichlorophenyl)pyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-isopropylthioaminopyrazole, 1 -(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-n-propyl thioaminopyrazole, 5-n-butylthioamino-1 -(2-chloro-4-trifluoromethylphenyl)-4-cyanopyrazole, 4cyano-5-ethylthioamino-1-(2,3,4-trichlorophenyl)pyrazole, and 1-(2-chloro-4-trifluoromethylphe nyl)-4-cyano-5-ethylthioaminopyrazole.

25. 4-Cyano-5-ethoxymethyleneamino-1-(2,3,4-trichlorophenyl)pyrazole, 1-(2-chloro-4-trifluoromethylphenyl)-4-cyano-5-ethoxymethyleneaminopyrazole, 4-cyano-5-ethoxymethyleneamino-1 (4-ethyl-2, 3,5, 6-tetrafluorophenyl)pyrazole, 4-cyano-1 -(2, 6-dichloro-4-trifluoromethylphenyl)-5- ethoxymethyleneaminopyrazole, 4-cyano-5-ethoxymethyleneamino- 1 -(2,3,5, 6-tetrafluoro-4-triflu- oromethylphenyl)pyrazole, 4-cyano-5-methoxymethyleneamino-1-(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-(1 -ethoxyethylideneamino) 1 -(2,3,4-trichlorophenyl)pyrazole, 4-cyano-5-n-propoxymethylene- 1 -(2,3,4-trichlorophenyl)pyrazole, 4cyano-5-(ethoxymethylene)amino- 1 -(2-nitro-4-trifluoro-methylphenyl)pyrazole, 1-(4-bromo-2,3,5,6-tetrafluorophenyl)-4-cyano-5-(ethoxymethylene)aminopyrazole, 4-cyano-1-(2,6-dibromo-4-trifluoromethylphenyl)-5-(ethoxymethylene)aminopyrazole, 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(diethylaminomethylene)aminopyrazole, 4-cyano-5-(ethoxymethylene)amino- 1 -pentafluorophenylpyrazole and 1 -(2-chloro-4-ethylphe- nyl)-4-cyano-5gethoxymethylene)aminopyrazole .

26. A process for the preparation of a compound of general formula ll depicted in claim 1, wherein A and B are as defined in claim 1 which comprises: (A) when A represents a group of general formula Ill depicted in claim 1, wherein Rl and R2 are as defined in claim 1, and B represents a group of general formula V depicted in claim 1, wherein R9, Rh, Ri, Bk and Rn are as defined in claim 1, reacting a compound of the general formula:

wherein R' and R2 are as defined in claim 1 and R3 represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, with a compound of the general formula:: B-NHNH2 IX wherein B is as defined in claim 1, or an acid addition salt thereof, (B) when A represents a group of general formula Ill depicted in claim 1, wherein R1 is as defined in claim 1 and R2 represents hydrogen atom or a group identical to the group represented by R, and B represents a group of general formula V depicted in claim 1, wherein R9, Rh, Ri, Bk, and Rn are as defined in claim 1, reacting a compound of the general formula:

wherein B is as defined in claim 1, or an alkali metal derivative thereof, with one or two molar proportions of a compound of the general formula:: R1X Xl, wherein R1 is as defined in claim 1 and X represents a chlorine, bromine or iodine atom, (C) when A represents a group of general formula Ill depicted in claim 1, wherein R1 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms, unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branchedchain alkoxycarbonyl group containing from 2 to 9 carbon atoms or one or more halogen atoms and R2 represents a hydrogen atom, and B represents a group of general formula V depicted in claim 1, wherein R9, Rh, Ri, Rk, and Rn are as defined in claim 1, reducing the imine double bond of a compound of the general formula:

wherein B is as defined in claim 1, R4 represents a straight- or branched-chain alkyl group containing up to 7 carbon atoms, unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms, or one or more halogen atoms, and R5 represents a hydrogen atom or a straightor branched-chain alkyl group containing up to 7 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms, or one or more halogen atoms, R4 and R5 together with the carbon atom to which they are attached representing a straight- or branched-chain alkyl group containing from 1 to 7 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms, or one or more halogen atoms, (D) when A represents a group of general formula Ill depicted in claim 1, wherein B1 is as defined in claim 1 and R2 represents a hydrogen atom, and B represents a group of general formula V depicted in claim 1, wherein Rg, Rh, Ri, Rk, and Rn are as defined in claim 1, removing the group R6CO- of a compound of the general formula:

wherein R1 and B are as defined in claim 1 and R6 represents a straight- or branched-chain alkyl or alkoxy group containing from 1 to 4 carbon atoms, (E) when A represents a group of general formula Ill depicted in claim 1 wherein R' and R2 each represent a methyl group and B represents a group of general formula V depicted in claim 1, wherein R9, Rh, Ri, Rk, and Rn are as defined in claim 1, reacting a compound of general formula X herein depicted, wherein B in general formula X is as defined in claim 1, with formic acid in the presence of acetic acid, (F) when A represents a group of general formula Ill depicted in claim 1 wherein R1 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, or one or more halogen atoms, and R2 represents a hydrogen atom, and B represents a group of general formula V depicted in claim 1, wherein Rs, Rh, Ri, Bk, and Rn are as defined in claim 1, reducing the carbonyl group of a compound of the general formula::

wherein R7 represents a straight- or branched-chain alkyl group containing from 1 to 7 carbon atoms unsubstituted or substituted by a cyano group, a hydroxy group, a straight- or branchedchain alkoxy group containing from 1 to 6 carbon atoms, or one or more halogen atoms, (G) when A represents a group of general formula Ill depicted in claim 1, wherein R' represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms and R2 as defined in claim 1 and B is as defined in claim 1, transesterifying the alkoxycarbonyl group of a compound falling within the definition given immediately above with an alkanol containing from 1 to 8 carbon atoms, wherein the alkoxy moiety of the aforesaid alkanol differs from the aforesaid alkoxycarbonyl substituent in the group R' with, when R2 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms, wherein the alkoxy moiety of the alkoxycarbonyl substituent on R2 differs from that of the alkanol used in the transesterification, simultaneous transesterification of the alkoxycarbonyl substituent in R2 to the same alkoxycarbonyl substituent in R' in the product obtained, (H) when A represents a group of general formula Ill depicted in claim 1, wherein R' represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms or alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms and R2 is as defined in claim 1, and B is as defined in claim 1, esterifying the carboxy group(s) of a compound of general formula II depicted in claim 1, wherein A represents a group of general formula Ill depicted in claim 1, wherein R' represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by a carboxy group or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms, substituted by a carboxy group and R2 is as defined in claim 1, and B is as defined in claim 1, with an alkanol containing from 1 to 8 carbon atoms, with, when R2 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon.atoms substituted by a carboxy group or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by a carboxy group simultaneous esterification of the carboxy group substituent on R2, (I) when A represents a group of general formula Ill depicted in claim 1, wherein R' represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms or alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an alkoxycarbonyl group containing from 2 to 9 carbon atoms, or substituted by an aminocarbonyl group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups each containing from 1 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8 carbon atoms and which, when the aminocarbonyl group is substituted by two alkenyl or alkynyl groups, may be the same or different, or substituted by an alkane-sulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, or substituted by a -COHet group, wherein Het is as defined in claim 1, or R' represents a straight- or branchedchain alkyl group containing from 1 to 8 carbon atoms or alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an alkoxyaminocarbonyl group wherein the alkoxy moiety contains from 1 to 8 carbon atoms and maybe straight or branched-chain, and R2 represents a hydrogen atom, and B is as defined in claim 1, reacting a compound of the general formula::

wherein B is as defined in claim 1 and R' represents a straight- or branched-chain alkylene group containing from 1 to 8 carbon atoms or a straight- or branched-chain alkenylene or alkynylene group containing from 2 to 8 carbon atoms, with a compound of the general formula: R8-H XVI wherein R8 represents a straight- or branched-chain alkoxy group containing from 1 to 8 carbon atoms, an amino group unsubstituted or substituted by one or two straight- or branched-chain alkyl groups containing from 1 to 8 carbon atoms and which, when the amine group is substituted by two alkyl groups, may be the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups containing from 2 to 8 carbon atoms and which, when the amino group is substituted by two alkenyl or alkynyl groups, may be the same or different, an alkoxyamino group wherein the alkoxy moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, an alkanesulphonamido group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, or a Het group as defined in claim 1, or when R8 represents an alkanesulphonamido group, an alkali metal salt of an alkanesulphonamide represented by general formula XVI, (J) when A represents a group of general formula Ill depicted in claim 1, wherein R' represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by an alkanesulphonamidocarbonyl group wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain and R2 represents a hydrogen atom, and B is as defined in claim 1, reacting a compound of general formula II depicted in claim 1, wherein A represents a group of general formula Ill depicted in claim 1, wherein R' represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by an unsubstituted aminocarbonyl group or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by an unsubstituted aminocarbonyl group, and R2 represents a hydrogen atom, and B is as defined in claim 1, with an alkanesulphonyl chloride, wherein the alkane moiety contains from 1 to 8 carbon atoms and may be straight- or branched-chain, (K) when A represents a group of general formula Ill depicted in claim 1,

wherein R' represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms substituted by a hydroxy group or a straight- or branched-chain alkenyl or alkynyl group containing from 3 to 8 carbon atoms substituted by a hydroxy group and R2 represents a hydrogen atom, and B is as defined in claim 1, reducing the carboxylic acid or ester group of a compound of the general formula::

wherein B is as defined in claim, R' represents a straight- or branched-chain alkylene group containing from 1 to 7 carbon atoms or a straight- or branched-chain alkenylene or alkynylene group containing from 2 to 7 carbon atoms, Ru represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms and T' represents a hydrogen atom or, when Ru represents an alkyl group, Tl may also represent a group R6(C = 0)-, wherein RB is as hereinbefore defined, (L) when A represents a group of general formula III depicted in claim 1, wherein R1 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms substituted by a chlorine atom or a straight- or branched-chain alkenyl or alkynyl group containing from 3 to 8 carbon atoms substituted by a chlorine atom and R2 represents a hydrogen atom, and B is as defined in claim 1, reacting a compound of general formula II depicted in claim 1, wherein A represents a group of general formula Ill depicted in claim 1, wherein R' represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms substituted by a hydroxy group or a straight- or branched-chain alkenyl or alkynyl group containing from 3 to 8 carbon atoms substituted by a hydroxy group, and R2 represents a hydrogen atom, and B is as defined in claim 1, with thionyl chloride.

(M) when A represents a group of general formula ill depicted in claim 1, wherein R' represents an alkylthio group wherein the alkyl moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain, and R2 represents a hydrogen atom and B is as defined in claim 1, reacting an alkali metal salt of a compound of general formula X depicted in claim 1, wherein B is as defined in claim 1, with an alkanesulphenyl chloride, wherein the alkane moiety contains from 1 to 4 carbon atoms and may be straight- or branched-chain, (N) when A represents a group of general formula IIIA depicted in claim 1, wherein RP represents a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms, and Rq is as defined in claim 1, and B is as defined in claim 1, reacting a compound of general formula X depicted in claim 1, wherein B is as defined in claim 1, with a compound of the general formula: Bw C(ORV)3 XVIII wherein R" represents a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms and R" represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, (0) when A represents a group of general formula IIIA depicted in claim 1, wherein RP represents an amino group substituted by one or two straight- or branched-chain alkyl groups each containing from 1 to 4 carbon atoms and which may be the same or different, and Rq is as defined in claim 1, and B is as defined in claim 1, reacting a compound of general formula II depicted in claim 1, wherein A represents a group of general formula IIIA depicted in claim 1, wherein RP represents a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms, and Rq is as defined in claim 1, and B is as defined in claim 1, with a mono- or di alkytamine wherein the alkyl moiety or moieties each contain from 1 to 4 carbon atoms and may be straight- or branched-chain, and which when the reaction is effected with a di-alkylamine, may be the same or different, (P) when A represents a group of general formula Ill wherein R1 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms unsubstituted or substituted in the alpha position by a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, and R2 represents a hydrogen atom, and B is as defined in claim 1, reducing the mine double bonds of a compound of the general formula:::

wherein B is as defined in claim 1, RV represents an alkyl group containing from 1 to 7 carbon atoms and T2 represents a hydrogen atom or a straight- or branched-chain alkoxy group containing from 1 to 6 carbon atoms, (Q) when A represents a group of general formula IV depicted in claim 1, wherein Ra, Rb, RC, Rd, Re, Rf and m are as defined in claim 1, and B represents a group of general formula V depicted in claim 1, wherein R9, Rh, Ri, Rk and R" are as defined in claim 1, treating a compound of the general formula::

wherein Ra, Rb, RC, Rd, Rf, m and B are as defined in claim 1 and X' represents a chlorine or bromine atom, with a base, or (R) when A represents a group of general formula Ill, wherein R1 represents a straight- or branched-chain alkyl group containing from 2 to 8 carbon atoms substituted by a carboxy group, a straight- or branched-chain alkoxycarbonyl group containing from 2 to 9 carbon atoms or an aminocarbonyl group unsubstituted or substituted by one or two straight- or branchedchain alkyl groups each containing from 1 to 8 carbon atoms-and which, when the aminocarbonyl group is substituted by two alkyl groups, maybe the same or different, or substituted by one or two straight- or branched-chain alkenyl or alkynyl groups each containing from 2 to 8 carbon atoms and which, when the aminocarbonyl groups is substituted by two alkenyl or alkynyl groups, may be the same or different, and R2 represents a hydrogen atom, and B is as defined in claim 1, treating a compound of general formula Il depicted in claim 1, wherein A represents a group of general formula IV depicted in claim 1, wherein Ra, Rb, RC, Rd, Re, R' and m are as defined in claim 1, with the proviso that the group of general formula IV contains from 2 to 8 carbon atoms excluding the carbon atom of the carbonyl group, and B is as defined in claim 1, to effect fission of the amide group of the group of general formula IV, with, respectively, an aqueous solution of an alkali metal hydroxide, a straight-or branched-chain alkanol containing from 1 to 8 carbon atoms in the presence of an alkali metal lower alkoxide or ethanolic hydrogen chloride, or ammonia or a mono- or di-alkylamine, wherein the alkyl moieties are straight- or branched-chain and each contain from 1 to 8 carbon atoms and which may, in the case of a dialkylamine, be the same or different, or a moni- or di-alkenyl- or alkynyl- amine, wherein the alkenyl or alkynyl moieties are straight- or branched-chain and each contain from 2 to 8 carbon atoms and which may, in the case of a di-alkenyl- or alkynyl- amine, be the same of different.

27. Process according to claim 26(A) wherein the reaction is effected in a suitable inorganic solvent at a temperature of from ambient temperature up to the reaction temperature of the reaction mixture and, when a compound of general formula IX is used, optionally in the presence of an alkali metal acetate, carbonate or bicarbonate, or, when an acid addition salt of a compound of general formula IX is used, in the presence of an alkali metal acetate, carbonate or bicarbonate.

28. Process according to claim 26(B) wherein the reaction is effected at a temperature of from O"C up to the reflux temperature of the reaction mixture, in the absence or presence of a suitable inert solvent and optionally in the presence of an acid-binding agent and optionally in the presence of a Crown ether.

29. Process according to claim 26(C) wherein the reduction of the imine double bond of the compound of general formula XII is effected with an alkali metal boro-or cyanoboro-hydride in the presence of a suitable inert organic solvent at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

30. Process according to claim 26(D) wherein R6 represents a straight- or branched-chain alkyl group and removal of the group R6CO- is effected by selective hydrolysis under mild alkaline conditions.

31. Process according to claim 26(D) wherein R6 represents a straight- or branched-chain alkoxy group containing from 1 to 4 carbon atoms and removal of the group R6CO- is effected by selective hydrolysis under mild alkaline or acidic conditions.

32. Process according to claim 26(E) wherein the reaction is effected in the absence or presence of a suitable inert organic solvent at a temperature of from 0 up to the reflux temperature of the reaction mixture and optionally at elevated pressure.

33. Process according to claim 26(F) wherein the reduction of the carbonyl group of the compound of general formula XIV is effected with an alkali metal boro-ethanedithioate in a suitable inert organic solvent at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

34.- Process according to claim 26(G) wherein transesterification is effected with an excess of the alkanol containing from 1 to 8 carbon atoms in the presence of an inorganic acid and optionally water at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

35. Process according to claim 26(H) wherein esterification is effected with the alkanol containing from 1 to 8 carbon atoms in the presence of an esterifying agent at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

36. Process according to claim 26(1) wherein the reaction is effected, when R8 represents an alkoxy group, in the presence of an excess of the alkanol represented by general formula XVI, or, when R8 represents an amino group unsubstituted or substituted by one or two alkyl, alkenyl or alkynyl groups, an alkanesulphonamido group, a Het group, or an alkoxyamino group, in the presence of a suitable inert organic solvent, in the presence when R8 represents an alkoxy group or an alkanesulphonamido group, of a base, or when R8 represents an amino group unsubstituted or substituted or a Het group or an alkoxyamino group, in the presence of an alkali metal carbonate or an excess of ammonia, mono- or di-alkyl-, alkenyl- or alkynyl- amine, alkoxyamine or the heterocyclic compound represented by general formula XVI, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

37. Process according to claim 26(J) wherein the reaction is effected at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture and optionally in the presence of a suitable inert organic solvent and optionally in the presence of a base.

38. Process according to claim 26(K) wherein Ru represents a hydrogen atom and reduction is effected with sodium dihydro-bis-(2-methoxyethoxy)-aluminate in the presence of a suitable inert organic solvent at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture, or Ru represents an alkyl group and reduction is effected with sodium borohydride in the presence of methanol and tertiary butanol at the reflux temperature of the reaction mixture.

39. Process according to claim 26(L) wherein the reaction is effected in a suitable inert organic solvent at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

40. Process according to claim 26(M) wherein the reaction is effected at 0 C in the presence of a suitable inert organic solvent and optionally in the presence of a Crown ether.

41. Process according to claim 26(N) wherein the reaction between compounds of general formulae X and XVIII is effected in the presence of an acid catalyst, and optionally in the presence of a suitable inert organic solvent, at the reflux temperature of the reaction mixture.

42. Process according to claim 26(N) wherein the reaction between compounds of general formulae X and XVIII is effected in the presence of a lower alkanol and optionally an inorganic acid at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

43. Process according to claim 26(0) wherein the reaction is effected in a suitable inert organic solvent at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

44. Process according to claim 26(0) or 43, wherein the reaction is effected in the presence of an excess of the mono- or di-alkylamine.

45. Process according to claim 26(P) wherein the reaction is effected with an alkali metal boro- or cyanoboro-hydride in the presence of a suitable inert organic solvent at a temperature of from OCC up to 60it.

46. Proces according to claim 26(Q) wherein the treatment with a base is effected with sodium hydride in a mixture of dichloromethane and dimethylformamide, potassium bicarbonate in ethanol and, optionally, water, potassium carbonate in acetone and, optionally, water, triethylamine in ethanol and, optionally, water, or Triton B in ethanol and, optionally, water, at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

47. Process according to claim 26(R) wherein the reaction is effected at a temperature of from laboratory temperature up to the reflux temperature of the reaction mixture.

48. Process according to claim 26 followed by the step of converting by methods known per sean N-phenylpyrazole derivative of general formula II depicted in claim 1 wherein A represents a group of general formula lil depicted in claim 1 herein R1 and/or R2 represents a straight- or branched-chain alkyl group containing from 1 to 8 carbon atoms substituted by a carboxy group, or a straight- or branched-chain alkenyl or alkynyl group containing from 2 to 8 carbon atoms substituted by a carboxy group, and B represents a group of general formula V depicted in claim 1, wherein R9, Rh, Ri, Rk, and Rn are as defined in claim 1, into a salt thereof with an agriculturally acceptable base.

49. Process for the preparation of N-phenylpyrazole derivatives of general formula 11 depicted in claim 1, wherein A and B are as defined in claim 1, substantially as hereinbefore described, with especially reference to Examples 23 to 48.

50. N-Phenylpyrazole derivatives of general formula II depicted in claim 1 wherein A and B are as defined in claim 1 or when appropriate salts thereof with agriculturally acceptable bases, when prepared by the process claimed in any one claims 26 to 49.

51. A herbicidal composition which comprises, as active ingredient, at least one Nphenylpyrazole derivative of general formula II depicted in claim 1, wherein A and B are as defined in claim 1, in association with one or more compatible herbicidally-acceptable diluents or carriers and/or surface active agents.

52. A herbicidal composition according to claim 51 which contains from 0.05 to 90% by weight of N-phenylpyrazole derivative(s).

53. A herbicidal composition according to claim 51 or 52 which contains from 0.05 to 25% of surface-active agent.

54. A herbicidal composition according to claim 51 or 52 which contains from 0.05 to 10% of surface-active agent.

55. A herbicidal composition according to any one of claims 51 to 54 in the form of dusts, granules or wettable powders.

56. A herbicidal composition according to any one of claims 51 to 54 in the form of aqueous, organic or aqueous-organic solutions, suspensions or emulsions.

57. A herbicidal composition according to any one of claims 51 to 54 and 56 in which the herbicidally-acceptable diluent is water.

58. A herbicidal composition according to claim 56 or 57 in the form of an aqueous suspension concentrate comprising from 10% to 70% w/v of one or more N-phenylpyrazole derivatives of general formula II depicted in claim 1, wherein A and B are as defined in claim 1, from 2 to 10% w/v of surface-active agent, from 0.1 to 5% w/v of thickener and water to 100% by volume.

59. A herbicidal composition according to claim 55 in the form of a wettable powder which comprises from 10 to 90% w/w of one or more N-phenylpyrazole derivatives of general formula II depicted in claim 1, wherein A and B are as defined in claim 1, from 2 to 10% w/w of surface-active agent and from 8 to 88% w/w of solid diluent or carrier.

60. A herbicidal composition according to claim 56 in the form of a liquid water soluble concentrate comprising from 5 to 50% w/v of one or more N-phenylpyrazole derivatives of general formula ll depicted in claim 1, wherein A and B are as defined in claim 1, from 5 to 25% w/v of surface-active agent and water-miscible solvent or a mixture of water-miscible solvent and water to 100% by volume.

61. A herbicidal composition according to claim 56 in the form of a liquid emulsifiable suspension concentrate which comprises from 10 to 70% w/v of one or more N-phenylpyrazole derivatives of general formula II depicted in claim 1, wherein A and B are as defined in claim 1, from 5 to 15% w/v of surface-active agent, from 0.1 to 5% w/v of thickener and organic solvent to 100% by volume.

62. A herbicide composition according to claim 55 in the form of granules comprising from 1 to 90% w/w of one or more N-phenylpyrazole derivatives of general formula II depicted in claim 1, wherein A and B are as defined in claim 1, from 0.5 to 7% w/w of surface-active agent and from 3 to 98.5% of granular carrier.

63. A herbicidal composition according to claim 56 in the form of an emulsifiable concentrate which comprises from 0.05 to 90% w/v of one or more N-phenylpyrazole derivatives of general formula II depicted in claim 1, wherein A and B are as defined in claim 1, from 0.01 to 10% w/v of surface-active agent and organic solvent to 100% by volume.

64. A herbicidal composition according to any one of claims 51 to 63 which contains one or more other pesticidally-active (including herbicidally-active) compounds.

65. A herbicidal composition according to any one of claims 51 to 64 in which the Nphenylpyrazole derivative(s) incorporated in the compositions is a compound claimed in any one of claims 2 to 25.

66. A herbicidal composition according to claim 51 substantially as hereinbefore described with especial reference to any one of Examples 1 to 22.

67. A method of controlling the growth of weeds at a locus which comprises applying to the locus a herbicidally effective amount of an N-phenylpyrazole derivative of general formula I depicted in claim 1, wherein A and B are as defined in claim 1, in a herbicidal composition as claimed in any one of claims 51 to 66.

68. A method according to claim 67 in which the weeds are broad-leafed weeds, such as those specifically mentioned in the Description.

69. A method according to claim 67 in which the weeds are grass weeds, such as those specifically mentioned in the Description.

70. A method according to claim 67, 68 or 69 wherein the N-phenylpyrazole derivative is applied pre- or post-emergence of the weeds.

71. A method according to claim 67 or 68 wherein the N-phenylpyrazole derivative is applied post-emergence of the weeds.

72. A method according to claim 67, 68, 69, 70 or 71 in which the herbicidal composition is applied to an area used, or to be used, for growing crops.

73. A method according to claim 72 in which the herbicidal composition is applied to a crop-growing area at a rate sufficient to control the growth of weeds without causing substantial permanent damage to the crop.

74. A method according to any one of claims 67 to 73 in which the N-phenylpyrazole derivative is applied at a rate between 0.01 kg and 10 kg per hectare.

75. A method according to claim 72, 73 or 74 in which the crop is a cereal, soya beans, field or dwarf bean, peas, lucerne, cotton, peanuts, flax, onions, carrots, cabbage, oilseed rape, sunflower, sugar beet, or permanent or sown grassland.

76. A method according to claim 72, 73 or 74 in which the crop is wheat, barley, oats, maize or rice.

77. A method according to any one of claims 72 to 76 in which the N-phenylpyrazole derivative is applied at a rate between 0.01 kg and 4.0 kg per hectare.

78. A method according to any one of claims 72 to 76 in which the N-phenylpyrazole derivative is applied at a rate between 0.01 kg and 2.0 kg per hectare.

79. A method according to claim 77 or 78 in which the herbicidal composition is applied for the control of broad-leafed weeds in an area used for growing a cereal crop before or after emergence of both the crop and weeds.

80. A method according to claim 79 in which the herbicidal composition is applied postemergence of the broad-leafed weeds.

81. A method according to claim 79 or 80 in which the N-phenylpyrazole derivative is applied at a rate between 0.01 kg and 4.0 kg per hectare.

82. A method according to claim 79 or 80 in which the N-phenylpyrazole derivative is applied at a rate between 0.01 kg and 2.0 kg per hectare.

83. A method according to any one claims 67 to 82 in which the N-phenylpyrazole derivative is a compound claimed in any one of claims 2 to 25.

84. A method of controlling the growth of weeds at a locus according to claim 67 substantially as herein before described.

85. Compounds of general formula Il depicted in claim 1, wherein A represents an openchain alkenylcarbonylamino group and B represents a group of general formula V depicted in claim 1, wherein Rg, Rh, Ri, Rk and R" are as defined in claim 1.

86. Compounds of the general formula:

wherein Ra, Rb, R', Re and Rf are as defined in claim 1 and B represents a group of general formula V depicted in claim 1, wherein Rg, Rh, RI, Rk and R" are as defined in claim 1.

87. Compounds of the general formula:

wherein R, Rb, RC, Rd and R' are as defined in claim 1, R9 and R10, which may be the same or different, each represent a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 3 carbon atoms, the combined total number of carbon atoms in R9 and R10 taken together being not more than three, and B represents a group of general formula V depicted in claim 1, wherein Rg, Rh, Ri, Rk and R" are as defined in claim 1.