Azole and azine derivatives are disclosed in W095/31448, W097/18198, W098/02424 and W098/05670.

The present invention provides a compound of formula (I) : wherein q is 0 or 1 ; B is N, N-oxide or CRI8 ; Y is 0, S or Nu 13 ; Z is 0, S or NR14 ; R57 is hydrogen, C1-lo alkyl, CH2 (C1-4 haloalkyl), C1-6 cyanoalkyl, C3-6 alkenyl, C3-6 alkynyl, C1-6 alkoxy (Cl-6) alkyl, Cl alkylthio (CI-6) alkyl, C1-6 alkoxy (C1-6) alkoxy (Cs 6) alkyl, Cl 6 alkylcarbonyl, benzyloxymethyl, benzoyloxymethyl, C2 alkenyl (C1-6)alkyl, C2-6 alkynyl (CI 6) alkyl, CI-10 alkoxycarbonyl, formyl, CI-6 alkylcarbonyl (Cl 6) alkyl, C1-6 alkoxycarbonyl (C1~6) alkyl, C1-6 alkylaminocarbonyl, di (CI-6) alkylaminocarbonyl, optionally substituted phenoxycarbonyl, optionally substituted phenyl (C, ~4) alkyl or S (O) rRa ; Ra is Cl 6 alkyl, Cl 6 haloalkyl or optionally substituted phenyl ; r is 0, 1 or 2 ; R58 is optionally substituted Cl 20 alkyl, optionally substituted C2-20 alkenyl, optionally substituted C2 20 alkynyl, optionally substituted C3 7 cycloalkyl, optionally substituted C5 6 cycloalkenyl, optionally substituted Cl 20 alkoxycarbonyl, optionally substituted Cl 20 alkylcarbonyl, aminocarbonyl, optionally substituted Cl 20 alkylaminocarbonyl, optionally substituted di (C1-20) alkylaminocarbonyl, optionally substituted aryloxycarbonyl, optionally substituted arylcarbonyl, optionally substituted arylaminocarbonyl, optionally substituted N-alkyl-N-arylaminocarbonyl, optionally substituted diarylaminocarbonyl, optionally substituted heteroaryloxycarbonyl, optionally substituted heteroarylcarbonyl,

optionally substituted heteroarylaminocarbonyl, optionally substituted alkylheteroarylaminocarbonyl, optionally substituted diheteroarylaminocarbonyl, R260, optionally substituted C1-20 alkylthio, optionally substituted C1-20 alkylsulfinyl, optionally substituted Cl 20 alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl, R28R29N or R310N=C (R27) ; Rl is hydrogen, halogen, optionally substituted C1~6 alkyl, optionally substituted C2 6 alkenyl, optionally substituted C2 6 alkynyl, optionally substituted C1-6 alkoxy, optionally substituted Co-6 alkylthio, optionally substituted ~3-7 cycloalkyl, cyano, nitro or SF5 ; Rl2 is hydrogen, halogen, optionally substituted C1~6 alkyl, optionally substituted C2 6 alkenyl, optionally substituted C2 6 alkynyl, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, cyano, nitro, formyl, R 32 ON=C (R"), optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl or SF5 ; or R'and R12 together with the atoms to which they are attached may be joined to form a five, six or seven- membered saturated or unsaturated ring carbocylic or heterocyclic ring which may contain one or two hetero atoms selected from 0, N or S and which may be optionally substituted by Cl 6 alkyl, Cl 6 haloalkyl or halogen ; Rl3 is hydrogen, cyano, nitro, optionally substituted C1~6 alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted (C2-6) alkenyl (C1-6)alkyl, optionally substituted (C2-6) alkynyl (CI-6) alkyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C1-6 alkylamino, optionally substituted di (CI-6) alkylamino, optionally substituted Cl 6 alkylcarbonylamino, optionally substituted C1-6 alkoxycarbonylamino, optionally substituted C1-6 alkoxy, optionally substituted C1-6 alkylthio, optionally substituted C1-6 alkylsulfinyl, optionally substituted C1-6 alkylsulfonyl, optionally substituted arylthio, optionally substituted arylsulfinyl, optionally substituted arylsulfonyl or C1-6acyloxy ; Rl4 is hydrogen, cyano, optionally substituted C1-8 alkyl, optionally substituted [C2 6 alkenyl (Ci-6) alkyl], optionally substituted [C2 6 alkynyl (C1-6) alkyl], optionally substituted ~3-7 cycloalkyl, optionally substituted [C3-7 cycloalkyl(C1-6)alkyl], C1-6 alkoxy(C1-6)alkyl, optionally substituted C1-6 alkoxycarbonyl, optionally substituted C1-6 alkylcarbonyl,

optionally substituted C1-6 alkylaminocarbonyl, optionally substituted di (C1-6)alkyl- aminocarbonyl, optionally substituted phenyl, optionally substituted heteroaryl, optionally substituted alkylsulfonyl or optionally substituted arylsulfonyl ; Rl8 is hydrogen, halogen, nitro, cyano, optionally substituted C1~8 alkyl, optionally substituted C2 6 alkenyl, optionally substituted C2 6 alkynyl, optionally substituted ~3-7 cycloalkyl, optionally substituted Cl alkoxycarbonyl, optionally substituted C1-6 alkylcarbonyl, optionally substituted C1~6 alkylaminocarbonyl, optionally substituted di (C1-6)alkyl-aminocarbonyl, optionally substituted phenyl or optionally substituted heteroaryl ; R26 is optionally substituted C1-2o alkyl, optionally substituted [C2-20 alkenyl (CI-6) alkyl], optionally substituted [C2-20 alkynyl (Ci-6) alkyl], optionally substituted C37 cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted [heterocyclyl (C1- 6) alkylCH=N] or di (CI-6) alkylC=N ; R28 and R29 are, independently, hydrogen, optionally substituted Cl 20 alkyl, optionally substituted ~3-7 cycloalkyl, optionally substituted [C2-20 alkenyl (Cs 6) alkyl], optionally substituted [C2-20 alkynyl-(C1-6)alkyl], optionally substituted ~1-20 alkoxycarbonyl, optionally substituted phenoxycarbonyl, formyl, optionally substituted C1-20 alkylcarbonyl, optionally substituted Cl 20 alkylsulfonyl or optionally substituted phenylsulfonyl ; or R28 and R29 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from 0, N or S and which may be optionally substituted by one or two Cl 6 alkyl groups ; R27 and R30 are independently hydrogen, optionally substituted phenyl or optionally substituted Cl 6 alkyl ; and R31 and R32 are, independently, hydrogen, optionally substituted phenyl (Cl 2) alkyl or optionally substituted C1-20 alkyl ; provided that R58 is not C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C2-6 alkenyl, C2-6 alkynyl, ~3-7 cycloalkyl, ~3-7 halocycloalkyl, ~3-7 cyanocycloalkyl, C1-3 alkyl (C3-7) cycloalkyl, C1-3 alkyl(C3-7)halocycloalkyl, C3-6 cycloalkyl (CI-6) alkyl, C5-6 cycloalkenyl, C5-6 cycloalkenyl (Cl 6) alkyl, C2-6 haloalkenyl, C1-6 cyanoalkenyl, C1-6 alkoxy (C1-6) alkyl, C-6 carboxyalkyl, C1-6 alkylcarbonyl (C1-6) alkyl, C1-6 alkoxycarbonyl (C1-6)alkyl, C1-6 alkylthio(C1-6)alkyl, C1-6 alkylsulfinyl(C1-6)alkylk, C1-6 alkylsulfonyl (Ci-6) alkyl, aminocarbonyl (C1-6)alkyl, C1-6 alkylaminocarbonyl (CI-6) alkyl, di (C1-6)alkylaminocarbonyl(C1-6)alkyl, C1-6 alkoxycarbonyl, C1~6 alkylcarbonyl,

aminocarbonyl, C1-6 alkylaminocarbonyl, di (C1~6) alkylaminocarbonyl, optionally substituted phenyl (C1-4) alkyl, optionally substituted phenyl (C2-4)alkenyl, optionally substituted heteroaryl (CI-) alkyl, optionally substituted heterocyclyl (CI-4) alkyl, a group ORb, a group S (O) pRC, a group NRdRe or a group C (Rf) =NORg ; where Rb is Cl 6 alkyl, C1-6 haloalkyl, C3-6 alkenyl, C1-4 cyanoalkyl, C1-6 alkoxycarbonyl(C1-6) alkyl, optionally substituted phenyl, optionally substituted phenyl (CI-) alkyl, optionally substituted heteroaryl, N=C (CH3) 2 ; Rc is C1-6 alkyl, C1-6 haloalkyl, C3-6 alkenyl, cyano, Cl4 cyanoalkyl, C1-6 alkoxycarbonyl (CI-6) alkyl, optionally substituted phenyl, optionally substituted phenyl (CI-4) alkyl or optionally substituted heteroaryl ; Rd and Re are, independently, hydrogen, C1-8 alkyl, C3-7 cycloalkyl, C3-6 alkenyl, C3~6 alkynyl, C2-6 haloalkyl, 1-6 alkoxy (CI 6) alkyl, C1-6 alkoxycarbonyl, optionally substituted phenoxycarbonyl, formyl, C1-6 alkylcarbonyl, C-6 alkylS02, optionally substituted phenyl02 or optionally substituted phenyl (CI4) alkyl ; Rf is C1~3 alkyl ; and RI is Cz-6 alkyl, optionally substituted phenyl (CI-2) alkyl ; p is 0, 1 or 2.

The compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.

Each alkyl moiety is a straight or branched chain and is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert- butyl or neo-pentyl. When present, the optional substituents on alkyl include one or more of halogen, nitro, cyano, NCS-, 3-7 cycloalkyl (which itself may be optionally substituted with C1~6 alkyl or halogen), C5-7 cycloalkenyl (which itself may be optionally substituted with C1~6 alkyl or halogen), hydroxy, Cm O alkoxy, CI-10 alkoxy (Cl-lo) alkoxy, tri (Cl4) alkylsilyl (CI-6) alkoxy, C1-6 alkoxycarbonyl(C1-10) alkoxy, Cl le haloalkoxy, CI-10 deuteroalkoxy, aryl (CI-4) alkoxy (where the aryl group may be further optionally substituted), C3-7 cycloalkyloxy (where the cycloalkyl group may be optionally substituted with C1-6 alkyl or halogen), Cl lo alkenyloxy, Cl-lo alkynyloxy, SH, Cl-lo alkylthio, C1-10 haloalkylthio, aryl (C1-4)alkylthio (where the aryl group may be further optionally substituted), C3-8 cycloalkylthio (where the cycloalkyl group may be optionally substituted with C1~6 alkyl or halogen), tri (C1-4)alkylsilyl(C1-6)alkylthio, arylthio (where

the aryl group may be further optionally substituted), C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, arylsulfonyl (where the aryl group may be further optionally substituted), tri (Ci-4) alkylsilyl, aryldi (Cl4) alkylsilyl, (C1-4) alkyldiarylsilyl, triarylsilyl, Cl-lo alkylcarbonyl, HO2C, CI-10 alkoxycarbonyl, aminocarbonyl, C1-6 alkylaminocarbonyl, di (CI-6 alkyl) aminocarbonyl, N- (CI-3 alkyl)-N- (Cl 3 alkoxy) aminocarbonyl, C1-6 alkylcarbonyloxy, arylcarbonyloxy (where the aryl group may be further optionally substituted), di (CI-6) alkylaminocarbonyloxy, aryl (which itself may be further optionally substituted), heteroaryl (which itself may be further optionally substituted), heterocyclyl (which itself may be optionally substituted with C1-6 alkyl or halogen), aryloxy, (which itself may be further optionally substituted), heteroaryloxy, (which itself may be further optionally substituted), heterocyclyloxy, (which itself may be optionally substituted with C1~6 alkyl or halogen), amino, C1-6 alkylamino, di (CI-6) alkylamino, alkylcarbonylamino, N-alkylcarbonyl-N-alkylamino.

One group of optional preferred substituents for alkyl include one or more of halogen, nitro, cyano, HO2C, Cl-lo alkoxy (itself optionally substituted by Cl In alkoxy), aryl (CI4) alkoxy, aryl (CI-) alkylthio, CI-10 alkylthio, CI-10 alkylcarbonyl, CI-10 alkoxycarbonyl, CI-6 alkylaminocarbonyl, di (Ci-6 alkyl) aminocarbonyl, (C1-6) alkyl- carbonyloxy, optionally substituted phenyl, aryl, heteroaryl, aryloxy, arylcarbonyloxy, heteroaryloxy, heterocyclyl, heterocyclyloxy, C3-7 cycloalkyl (itself optionally substituted with (Cl 6) alkyl or halogen), ~3-7 cycloalkyl (itself optionally substituted with (Ci-6) alkyl or halogen) oxy, ~3-7 cycloalkyl (itself optionally substituted with (CI-6) alkyl or halogen) thio, ~5-7 cycloalkenyl, C1-6 alkylsulfonyl, C1-6 alkylsulfinyl, tri (C1-4) alkylsilyl, tri (CI-) alkyl-silyl (Cl 6) alkoxy, tri (CI-4) alkylsilyl (CI-6) alkylthio, aryldi (Cl4) alkylsilyl, (C1-4) alkyl-diarylsilyl, triarylsilyl, phenoxy (itself optionally substituted by halogen, Cl4 alkyl or heteroaryloxy (itself optionally substituted by halogen)), C7-) bicycloalkane, C7- bicycloalkene and (Cl l5 alkylcarbonyl) (CI-4 alkyl) amino.

Alkenyl and alkynyl moieties can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the (D-or (Z)-configuration.

Examples are vinyl, allyl and propargyl. When present, the optional substituents on alkenyl or alkynyl include one or more of the substituents listed above for alkyl but

especially preferred substituents are one or more of halogen, aryl, Cl 6 alkyl, C3 7 cycloalkyl, C5-7 cycloalkenyl (itself optionally substituted by C1~6 alkyl) and Cl 6 alkoxycarbonyl.

In the context of this specification acyl is optionally substituted Cl 6 alkylcarbonyl (for example acetyl), optionally substituted C2 6 alkenylcarbonyl, optionally substituted C2-6 alkynylcarbonyl, optionally substituted arylcarbonyl (for example benzoyl) or optionally substituted heteroarylcarbonyl.

Halogen is fluorine, chlorine, bromine or iodine.

Haloalkyl groups are alkyl groups which are substituted with one or more of the same or different halogen atoms and are, for example, CF3, CF2C1, CF3CH2 or CHF2CH2.

Aryl includes naphthyl, anthracyl, fluorenyl and indenyl but is preferably phenyl.

The term heteroaryl refers to an aromatic ring containing up to 10 atoms including one or more heteroatoms (preferably one or two heteroatoms) selected from 0, S and N.

Examples of such rings include pyridine, pyrimidine, furan, quinoline, quinazoline, pyrazole, thiophene, thiazole, oxazole and isoxazole.

The terms heterocycle and heterocyclyl refer to a non-aromatic ring containing up to 10 atoms including one or more (preferably one or two) heteroatoms selected from 0, S and N. Examples of such rings include 1, 3-dioxolane, tetrahydrofuran and morpholine.

It is preferred that heterocyclyl is optionally substituted by CI-6 alkyl.

Cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl. The optional substituents for cycloalkyl include one or more of the substituents listed above for alkyl but preferred substituents are one or more of halogen, cyano, C1~3 alkyl (itself optionally substituted by halogen), C2 6 alkenyl (itself optionally substituted by halogen), C2 6 alkynyl (itself optionally substituted by halogen) and phenyl (itself optionally substituted by halogen), especially halogen, cyano, Cl 3 alkyl, Cl 3 alkyl (C2 4) alkenyl and phenyl (itself optionally substituted by halogen).

Cycloalkenyl includes cyclopentenyl and cyclohexenyl. The optional substituents for cycloalkenyl include one or more of the substituents listed above for alkyl but especially preferred substituents include one or more of Cl 3 alkyl, halogen and cyano.

Carbocyclic rings include aryl, cycloalkyl and cycloalkenyl groups.

For substituted aryl such as phenyl and heteroaryl groups the substituents are independently selected from one or more of halogen, nitro, cyano, NCS-, CI-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy (CI-6) alkyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, ~3-7 cycloalkyl (which itself may be optionally substituted with C1~6 alkyl or halogen), ~5-7 cycloalkenyl (which itself may be optionally substituted with Ci-6 alkyl or halogen), hydroxy, Cl-lo alkoxy, Cl-lo alkoxy (C1-10)alkoxy, tri (C1-4)alkylsilyl(C1-6)alkoxy, C1-6 alkoxycarbonyl (C1-10) alkoxy, Cl lu haloalkoxy, Cl-lo deuteroalkoxy, aryl (CI-) alkoxy (where the aryl group may be further optionally substituted), ~3-7 cycloalkyloxy (where the cycloalkyl group may be optionally substituted with C1~6 alkyl or halogen), Cl-lo alkenyloxy, Cl lO alkynyloxy, SH, Cl-lo alkylthio, Cl in haloalkylthio, aryl (CI-) alkylthio (where the aryl group may be further optionally substituted), ~3-7 cycloalkylthio (where the cycloalkyl group may be optionally substituted with C1~6 alkyl or halogen), tri (CI4) alkylsilyl (Cl 6) alkylthio, arylthio (where the aryl group may be further optionally substituted), , C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, arylsulfonyl (where the aryl group may be further optionally substituted), tri (C1-4)alkylsilyl, aryldi (C1-4)alkylsilyl, (C1-4) alkyldiarylsilyl, triarylsilyl, Cl lu alkylcarbonyl, H02C, CI-10 alkoxycarbonyl, aminocarbonyl, C1-6 alkylaminocarbonyl, di (CI-6 alkyl) aminocarbonyl, N- (CI-3 alkyl)-N- (CI-3 alkoxy) aminocarbonyl, C1-6 alkylcarbonyloxy, arylcarbonyloxy (where the aryl group may be further optionally substituted), di (CI-6) alkylaminocarbonyloxy, aryl (which itself may be further optionally substituted), heteroaryl (which itself may be further optionally substituted), heterocyclyl (which itself may be optionally substituted with C-6 alkyl or halogen), aryloxy, (which itself may be further optionally substituted), heteroaryloxy, (which itself may be further optionally substituted), heterocyclyloxy, (which itself may be optionally substituted with CI-6 alkyl or halogen), amino, C1-6 alkylamino, di (C1- 6) alkylamino, alkylcarbonylamino, N-alkylcarbonyl-N-alkylamino.

For substituted heterocyclyl groups the substituents include one or more of the substituents listed above for alkyl. For substituted phenyl moieties, heterocyclyl and heteroaryl groups one set of preferred substituents are independently selected from one or more of halogen, C,-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy (C, 6) alkyl, C,-6 alkoxy, C1-6

haloalkoxy, CI-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, Cl 6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C2-6 alkenyl, C2-6 haloalkenyl, C2-6 alkynyl, C3-7 cycloalkyl, nitro, cyano, CO2H, CI-6 alkylcarbonyl, C-6 alkoxycarbonyl, R4lR42N or R43 ENC (O) wherein R41, R42, R43 and R44 are, independently, hydrogen or C1-6 alkyl.

It is to be understood that dialkylamino substituents include those where the dialkyl groups together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from 0, N or S and which may be optionally substituted by one or two C1-6 alkyl groups. When heterocyclic rings are formed by joining two groups on an N atom, the resulting rings are suitably pyrrolidine, piperidine, thiomorpholine and morpholine each of which may be substituted by one or two (Ci-6) alkyl groups.

In a further aspect, the present invention provides a compound of formula (IA) : wherein q, B, Y, Z, Rl, R12, R57 and R58 are as defined above for a compound of formula (I).

More preferred compounds of formula (IA) are those wherein R'is hydrogen, halogen, CI-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 cyanoalkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, CI-6 alkylthio, C-6 haloalkylthio, C3~6 cycloalkyl, C3-7 cycloalkyl (Cl 4) alkyl, C1-6 alkoxy (CI-6) alkyl, cyano, nitro or SF5 ; B is N or CRIB ; Y is 0, S or NRI3 ; Z is 0, S or NR14 ; R57 is hydrogen, C1-10 alkyl, benzyloxymethyl, benzoyloxymethyl, C1-6alkoxy(C1-6)alkyl, C2-6 alkenyl (CI-6) alkyl, C2-6 alkynyl (Cl 6) alkyl, CI-10 alkylcarbonyl or C1-10 alkoxycarbonyl ; R58 is C9-20 alkyl, C14 alkyl (having substituents chosen from C 6 alkylcarbonyloxy, aryl (C1-4) alkoxy, C7 l0 bicycloalkane, C7-10 bicycloalkene, phenoxy [itself having substituents chosen from halogen, C1-4 alkyl and halo-substituted heteroaryloxy] or (Ci-is alkylcarbonyl) (CI 4 alkyl) amino), C1-4 alkyl substituted by both

halogen and C7 1o bicycloalkane, Cl 4 alkyl substituted by both halogen and C7-10 bicycloalkene, C2-6 alkenyl (having substituents chosen from C5 7 cycloalkenyl (itself substituted by C 1-6 alkyl) and Cl-6 alkoxycarbonyl), C3-7 cycloalkyl (itself having substituents chosen from C1~3 alkyl, C1~3 alkyl (C2~4) alkenyl, and phenyl (itself optionally substituted by halogen)), C7-20 alkyl carbonyl, aryl carbonyl (having substituents chosen from Cl4 alkyl and halogen), CI-2ohaloalkylaminocarbonyl, di (CI-20) alkylaminocarbonyl (where at least one one alkyl group has substituents chosen from halogen), C7-20 alkylaminocarbonyl, di (C7 20) alkylaminocarbonyl, C7 20 alkoxy (optionally substituted by halogen), C7-2o alkylsulfinyl (optionally substituted by halogen), C-6 haloalkylsulfinyl or C5-6 cycloalkenyl (substituted by C1~3 alkyl) ; R12 is hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, C1-6 alkynyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 alkoxy (Ci-6) alkyl, C1-6 haloalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, Ci-6 haloalkylsulfonyl, CI-6 haloalkyl, cyano, nitro, formyl, CH=NOR32, Ci- 6 alkylcarbonyl, C1-6 alkoxycarbonyl or SF5 ; or together Rl and RIZ together with the atoms to which they are attached may be joined to form a five, six or seven-membered saturated or unsaturated ring carbocylic or heterocyclic ring which may contain one or two hetero atoms selected from 0, N or S and which may be optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen ; RI3 is cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, C3-7 cycloalkyl, C3-7 cycloalkyl (Cl-6) alkyl, CH2 (C2-6) alkenyl, CH2 (C2-6) alkynyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) heteroaryl (optionally substituted by halo, nitro, cyano, Ci. alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-6 alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 alkylamino, di (CI-6) alkylamino, C1-6 alkylcarbonylamino, Cl 6 alkoxycarbonylamino, Cl 6 alkoxy, Ci-6 alkylthio, C1-6 alkylsulfinyl, CI-6 alkylsulfonyl, C1-6 haloalkylthio, C1-6 haloalkylsulfinyl, C1-6 haloalkylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl or OCO (Cl 6) alkyl ; R14 is hydrogen, C,-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C2-6 alkenyl, C2-6 alkynyl, C3 cycloalkyl, C2-6 haloalkenyl, C3 cycloalkyl(C1-6) alkyl, CI-6 alkoxy (C1- 6) alkyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, C1-6 alkylaminocarbonyl, di (C1- 6) alkylaminocarbonyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or heteroaryl (optionally substituted by halo,

nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) ; R18 is hydrogen, halogen, nitro, cyano, C1-8 alkyl, C1-6 haloalkyl, C1-6 cyanoalkyl, C26 alkenyl, C2-6 alkynyl, ~3-7 cycloalkyl, C2-6 haloalkenyl, C3-7 cycloalkyl (C1-6)alkyl, C1-6 alkoxy(C1- 6) alkyl, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, Ci-6alkylaminocarbonyl, di (C1- 6) alkylaminocarbonyl, C1-6 alkoxycarbonyl (C1-6)alkyl, C1-6 alkylcarbonyl (Ci-6) alkyl, C1-6 alkylaminocarbonyl (CI 6) alkyl, di (CI-6) alkylamino-carbonyl (CI 6) alkyl, phenyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), phenyl (C1-6) alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1~6 alkyl, C1~6 haloalkyl, CI~6 alkoxy or C1-6 haloalkoxy), heteroaryl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) or heteroaryl (C1-6) alkyl (wherein the heteroaryl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy) ; R26 is Cl 8 alkyl, C-6 haloalkyl, C-6 cyanoalkyl, C2 6 alkenyl, C2-6 alkynyl, C1-6 alkoxy (CI-6) alkyl, phenyl (C1-4) alkyl, (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or Cl 6 haloalkoxy), heteroaryl (CI-) alkyl (wherein the heteroaryl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl (optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), heterocyclyl (CI4) alkyl (wherein the heterocyclyl group is optionally substituted by halo, nitro, cyano, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), C1-6 alkoxycarbonyl (CI-6) alkyl or N=C (CH3) 2 ; R27 is Cl 6 alkyl, Cl 6 haloalkyl or phenyl (optionally substituted by halo, nitro, cyano, CI-6 alkyl, Cl 6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy), R28 and R29 are, independently, hydrogen, Cl 8 alkyl, C37 cycloalkyl, C3~6 alkenyl, C3~6 alkynyl, C37 cycloalkyl (CI-4) alkyl, C2-6 haloalkyl, C1-6 alkoxy (CI-6) alkyl, C1-6 alkoxycarbonyl, or R28 and R29 together with the N atom to which they are attached form a five, six or seven-membered heterocyclic ring which may contain one or two further hetero atoms selected from 0, N or S and which may be optionally substituted by one or two Cl 6 alkyl groups ; R31 and R32 are, independently, Cl 6 alkyl or phenyl (Ci-2) alkyl (wherein the phenyl group is optionally substituted by halo, nitro, cyano, C-6 alkyl, C,-6 haloalkyl, C,-6 alkoxy or C1-6 haloalkoxy). Additionally R58

may be ~3-7 cycloalkyl having substituents chosen from C24 haloalkyl, C2-4 alkenyl, C2 4 haloalkenyl, C2-4 alkynyl or ~3-4 haloalkynyl. q is preferably 0.

B is preferably N.

Y is preferably O or S.

Z is preferably O or S.

R57 is preferably hydrogen, C1-10 alkyl, benzyloxymethyl, benzoyloxymethyl, C1-6alkoxy(C1-6) alkyl, C2-6 alkenyl (CI-6) alkyl (especially allyl), C2-6 alkynyl (C1-6) alkyl (especially propargyl), Cl-lo alkylcarbonyl or Cl 1e alkoxycarbonyl (especially isobutoxycarbonyl).

R58 is preferably C9 20 alkyl, Cl4 alkyl (having substituents chosen from C1-6 alkylcarbonyloxy, aryl (C1-4) alkoxy, C7-) bicycloalkane, C7-10 bicycloalkene, phenoxy [itself having substituents chosen from halogen, C » alkyl and halo-substituted heteroaryloxy] or (Cl l5 alkylcarbonyl) (C1-4 alkyl) amino), C1-4 alkyl substituted by both halogen and C7 IO bicycloalkane, C1-4 alkyl substituted by both halogen and C7 1o bicycloalkene, ~2-6 alkenyl (having substituents chosen from C5 cycloalkenyl (itself substituted by C1-6 alkyl) and C1-6 alkoxycarbonyl), ~3-7 cycloalkyl (itself having substituents chosen from C1-3 alkyl, C1-3 alkyl (C2-4) alkenyl and phenyl (itself optionally substituted by halogen)), C7 20 alkyl carbonyl, aryl carbonyl (having substituents chosen from Cl 4 alkyl and halogen), C1-20 haloalkylaminocarbonyl, di (C1-20)alkylaminocarbonyl (where at least one one alkyl group has substituents chosen from halogen), C7-20 alkylaminocarbonyl, di (C7-20) alkylaminocarbonyl, C7-20 alkoxy (optionally substituted by halogen), C7 20 alkylsulfinyl (optionally substituted by halogen), C-6 haloalkylsulfinyl or C5-6 cycloalkenyl (substituted by 1-3 alkyl). Additionally R58 may be C3 7 cycloalkyl having substituents chosen from C24 haloalkyl, C2-4 alkenyl, C2-4 haloalkenyl, C2-4 alkynyl or ~3-4 haloalkynyl.

R1 is preferably hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, C1-6 haloalkyl, C1-6 alkoxy, C-6 alkoxy (Cl-6) alkyl, C1-6 haloalkoxy, C1-6 alkylthio, C-6 haloalkylthio, C3~6 cycloalkyl, cyano, nitro or SF5, especially hydrogen, halogen, C1-6 alkyl, C2-6 alkenyl, CI-6

haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylthio, C-6 haloalkylthio, C3~6 cycloalkyl, cyano, nitro or SF5.

Rl2 is preferably hydrogen, halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkoxy (Cl 6) alkyl, CI~6 alkylthio or SF5 ; alternatively R I and R 12 together with the atoms to which they are attached form a benzene ring optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen ; or form a cyclopentyl or cyclohexyl ring optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen.

Y is more preferably 0.

Z is more preferably 0.

Rl is more preferably halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy or C1-6 haloalkoxy.

R12 is more preferably halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 alkoxy (CI-6) alkyl or C1-6 haloalkoxy. Alternatively R'and R12 together with the atoms to which they are attached form a benzene ring optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen ; or form a cyclopentyl or cyclohexyl ring optionally substituted by C1-6 alkyl, C1-6 haloalkyl or halogen.

R57 is more preferably hydrogen, C1-10 alkyl or Cl 6alkoxy (Cl 6) alkyl.

R58 is more preferably C9 20 alkyl, Cl 4 alkyl (having substituents chosen from C1-6 alkylcarbonyloxy, aryl (CI-4) alkoxy, C7 1o bicycloalkane, C7-10 bicycloalkene, phenoxy [itself having substituents chosen from halogen, Cl4 alkyl and halo-substituted heteroaryloxy] or (Ci-is alkylcarbonyl) (C1-4 alkyl) amino), Cl 4 alkyl substituted by both halogen and C7-10 bicycloalkane, Cl 4 alkyl substituted by both halogen and C7-10 bicycloalkene, C2-6 alkenyl (having substituents chosen from C5 7 cycloalkenyl (itself substituted by C-6 alkyl) and Ci. alkoxycarbonyl) or C3 cycloalkyl (itself having substituents chosen from C1-3 alkyl, C2-4 haloalkyl, (C2-4) alkenyl, (C2-4) haloalkenyl, 2-4 alkynyl, C3 4haloalkynyl and phenyl (itself optionally substituted by halogen)) ; additionally R58 may be C3 7 cycloalkyl having substituents chosen from C2-4 haloalkyl, C2-4 alkenyl, C2 4 haloalkenyl, C24 alkynyl or C3 4 haloalkynyl.

RI is most preferably methyl, ethyl or methoxymethyl.

R12 is most preferably methyl or halogen (especially chloro and bromo), or Rl and R12 together with the carbon atoms to which they are attached form a cyclopentyl or cyclohexyl ring optionally substituted by methyl.

The compounds in the following Table illustrate compounds of the invention.

Table 1 provides 39 compounds of formula (IA) wherein q is 0 ; R1 is methyl ; R12 is chloro ; B is N ; Y is O ; Z is O ; and R57 and R58 are as defined in Table 1.

TABLE 1 Compound R57 R58 no. 1 H CH3CO2CH2 2 H benzyloxymethyl 3 H 2-(2, 2, 3-trimethylpent-4-enyl) vinyl 4 H (bicyclo [2. 2. 1] heptan-2-yl) CHCI 5 H (bicyclo [2. 2. 1] heptan-2-yl) methyl 6 H 1-(2, 4-dichlorophenoxy) ethyl 7 H C2H5CO2CH=CH 8 H [2,2-dimethyl-3-(2-methylprop-1-enyl)]cyclopropyl 1-(4-chlorophenyl) cyclopropan-1-yl 10 H (2, 4-dichlorophenoxy) methyl 11 H (2, 4, 5-trichlorophenoxy) methyl 12 H (2, 4, 6-trichlorophenoxy) methyl 13 H 1-(2, 4, 5-trichlorophenoxy) ethyl 14 H 1- [4- (3, 5-dichloropyridin-2-yloxy) phenoxy] ethyl 15 H 4- (5-trifluoromethylpyridin-2-yloxy) phenyl 16 H [N- (n-dodecanoyl), N-methyl] aminomethyl 17 H CH3 (CH2) i4 18 H 4-(2, 6-difluoro-4-trifluoromethylphenoxy) phenyl 19 H 4-phenylbenzyl TABLE 1 Continued 20 H 2, 2-dimethyl-3-hydroxypropyl 21 H 2-methyl-2-formylpropyl 22 H (4-trifluoromethylphenoxy) phenyl 23 H 2, 2-dimethyl-3-methoxyiminopropyl 24 CH20CH2CH3 2, 2-dimethyl-3-hydroxypropyl 25 H 4- (4-chlorophenyl) benzyl 26 CH20CH2CH3 (bicyclo [2. 2. 1] heptan-2-yl) methyl 27 CH20CH2CH3 (1-cyclopentyl-2-ethoxy) ethyl 28 CH20CH2CH3 1- (4-chlorophenyl) cyclopropyl 29 phenoxymethyl 2, 2-dimethylpropyl 30 H cis- [3- (2-chloro-3, 3, 3-trifluoropropenyl)-2, 2- dimethyl] cyclopropyl 31 H cis- [3-(2, 2-dichlorovinyl)-2, 2-dimethyl] cyclopropyl 32 H trans- [3- (2, 2-dichlorovinyl)-2, 2-dimethyl] cyclopropyl 33 H cis- [3- (2, 3, 3, 3-tetrafluoropropenyl)-2, 2- dimethyl] cyclopropyl 34 H cis- [3- (2, 2-dichloro-3, 3, 3-trifluoropropyl)-2, 2- dimethyl] cyclopropyl 35 H trans- [2, 2-dimethyl-3- (3, 3, 3-trifluro-2- trifluromethylpropenyl)] cyclopropyl 36 trans-(2, 2-dimethyl-3-trifluoropropynyl) cyclopropyl 37 CH20CH2CH3 trans- [2, 2-dimethyl-3- (3, 3, 3-trifluro-2- trifluromethylpropenyl)] cyclopropyl 38 CH20CH2CH3 trans- [3- (2, 2-dichlorovinyl)-2, 2-dimethyl] cyclopropyl 39 CH20CH2CH3 trans- (2, 2-dimethyl-3-trifluoropropynyl) cyclopropyl The following abbreviations are used throughout this description : m. p. = melting point ppm = parts per million s = singlet br = broad d = doublet dd = doublet of doublets t= triplet q = quartet m = multiplet Table 2 shows selected melting point and selected NMR data, all with CDC13 as the solvent (unless otherwise stated ; if a mixture of solvents is present, this is indicated as, for example, (CDC13/d6-DMSO)).

TABLE 2 Compound Melting NMR proton shifts (/ppm) No point (/°C) (CDC13 unless otherwise stated.) 1 143-144 2. 20 (3H, s) ; 2. 38 (3H, s) ; 4. 00 (2H, s) ; 5. 35 (2H, m) ; 7. 35 (lH, dd) ; 7. 60 (lH, d) ; 7. 70 (lH, d) ; 8. 13 (lH, br). 2 144-145 2. 39 (3H, s) ; 4. 00 (2H, s) ; 4. 71 (2H, s) ; 4. 80 (2H, s) ; 7. 35 (6H, m) ; 7. 60 (lH, d) ; 7. 70 (lH, d) ; 8. 10 (lH, br). 3 0. 85 (3H, s) ; 1. 05 (3H, s) ; 1. 60 (3H, s) ; 2. 00 (2H, m) ; 2. 38 (3H, s) ; 3. 98 (2H, s) ; 5. 25 (lH, br) ; 6. 50 (lH, m) ; 7. 10 (lH, m) ; 7. 28 (lH, dd) ; 7. 52 (lH, d) ; 7. 62 (1H, d) ; 8. 1 (1H, br). 4 1. 1-1. 75 (10H, m) ; 2. 38 (3H, s) ; 2. 45 (1H, m) ; 4. 0 (2H, s) ; 4. 7 (lH, d) ; 7. 38 (lH, dd) ; 7. 6 (1H, d) ; 7. 7 (1H, d) ; 8. 25 (1H, br). 5 1. 10-1. 60 (10H, m) ; 2. 38 (3H, s) ; 2. 75-2. 90 (2H, m) ; 3. 98 (2H, s) ; 7. 28 (1H, dd) ; 7. 52 (1H, d) ; 7. 62 (lH, d) ; 8. 20 (lH, br). 6 1. 95 (3H, d) ; 2. 40 (3H, s) ; 4. 00 (2H, s) ; 5. 55 (1H, m) ; 7. 00 (1H, d) ; 7. 10 (lH, m) ; 7. 35 (2H, m) ; 7. 60 (1H, d) ; 7. 70 (lH, d) ; 8. 10 (1H, br). 7 1. 38 (3H, t) ; 2. 40 (3H, s) ; 4. 00 (2H, s) ; 4. 32 (2H, q) ; 7. 02 (1H, d) ; 7. 40 (1H, dd) ; 7. 58 (1H, d) ; 7. 60 (1H, d) ; 7. 74 (1H, d) ; 8. 10 (1H, br). 8 1. 23 (6H, s) ; 1. 75 (6H, s) ; 2. 35 (1H, m) ; 2. 38 (3H, s) ; 3. 98 (2H, s) ; 5. 02 (1H, m) ; 7. 25 (lH, dd) ; 7. 50 (lH, d) ; 7. 60 (lH, d) ; 8. 06 (lH, br). 9 1. 5 (2H, m) ; 1. 89 (2H, m) ; 2. 38 (3H, s) ; 3. 95 (2H, s) ; 7. 22 (lH, dd) ; 7. 38 (2H, d) ; 7. 43 (3H, m) ; 7. 58 (lH, d) ; 8. 03 (1H, br). 10 2. 38 (3H, s) ; 4. 01 (2H, s) ; 5. 4 (2H, s) ; 7. 06 (1H, dd) ; 7. 2 (lH, dd) ; 7. 38 (2H, m) ; 7. 62 (1H, d) ; 7. 72 (1H, d) ; 8. 06 (1H, br). 11 1. 95 (3H, d) ; 2. 39 (3H, s) ; 4. 0 (2H, s) ; 5. 55 (1H, q) ; 7. 22 (1H, s) ; 7. 36 (1H, dd) ; 7. 46 (1H, s) ; 7. 62 (1H, d) ; 7. 72 (1H, d) ; 8. 1 (1 H, br). 12 2. 39 (3H, s) ; 4. 0 (2H, s) ; 5. 3 (2H, s) ; 7. 25 (1H, s) ; 7. 32 (lH, s) ; 7. 4 (1H, dd) ; 7. 66 (1H, d) ; 7. 73 (lH, d) ; 8. 07 (1H, br).

TABLE 2 Continued 13 1. 14 (3H, t) ; 2. 3 (2H, m) ; 2. 38 (3H, s) ; 4. 0 (2H, s) ; 7. 18 (lH, s) ; 7. 36 (lH, dd) ; 7. 46 (lH, s) ; 7. 6 (lH, d) ; 7. 72 (lH, d) ; 8. 11 (1 H, br). 14 1. 88 (3H, d) ; 2. 38 (3H, s) ; 3. 98 (2H, s) ; 5. 58 (lH, m) ; 7. 05 (4H, m) ; 7. 33 (lH, dd) ; 7. 59 (lH, d) ; 7. 7 (lH, d) ; 7. 72 (lH, m) ; 7. 92 (lH, m) ; 8. 12 (lH, br). 15 2. 38 (3H, s) ; 4. 02 (2H, s) ; 7. 12 (lH, d) ; 7. 33 (3H, m) ; 7. 62 (lH, d) ; 7. 72 (lH, d) ; 7. 96 (lH, m) ; 8. 22 (lH, br) ; 8. 32 (2H, m) ; 8. 48 (lH, m). 16 0. 89 (3H, t) ; 1. 3 (14H, br) ; 1. 69 (4H, m) ; 2. 38 (3H, s) ; 2. 48 (2H, m) ; 3. 2 (3H, s) ; 3. 98 (2H, s) ; 4. 89 (2H, s) ; 7. 28 (1H, dd) ; 7. 52 (1H, d) ; 7. 63 (lH, d) ; 8. 18 (1H, br). 17 0. 89 (3H, t) ; 1. 25 (24H, br) ; 1. 89 (2H, m) ; 2. 38 (3H, s) ; 2. 95 (2H, t) ; 3. 98 (2H, s) ; 7. 28 (lH, dd) ; 7. 53 (1H, d) ; 7. 63 (lH, d) ; 8. 06 (1H, br). 18 188-190 2. 37 (3H, s) ; 4. 0 (2H, s) ; 7. 35 (3H, m) ; 7. 52 (2H, m) ; 7. 62 (1H, d) ; 7. 72 (1H, d) ; 8. 04 (1H, dd) ; 8. 1 (2H, br) 19 2. 38 (3H, s) ; 3. 98 (2H, s) ; 4. 33 (2H, s) ; 7. 48 (12H, m) ; 8. 1 (1 H, br) 20 168-169 1. 05 (6H, s) ; 2. 38 (3H, s) ; 2. 82 (1H, t) ; 2. 95 (2H, s) ; 3. 98 (2H, s) ; 7. 28 (1H, dd) ; 7. 53 (1H, d) ; 7. 62 (lH, d) ; 8. 23 (lH, br) 21 125-127 1. 24 (6H, s) ; 2. 38 (3H, s) ; 3. 16 (2H, s) ; 3. 98 (2H, s) ; 7. 28 (1H, dd) ; 7. 52 (1H, d) ; 7. 62 (1H, d) ; 8. 18 (1H, br) ; 9. 68 (lH, s) 22 157-158 2. 38 (3H, s) ; 3. 98 (2H, s) ; 4. 3 (2H, s) ; 7. 05 (3H, m) ; 7. 28 (lH, dd) ; 7. 4 (2H, m) ; 7. 55 (3H, m) ; 7. 66 (lH, d) ; 8. 09 (lH, br) 23 1. 25 (6H, s) ; 2. 38 (3H, s) ; 3. 08 (2H, s) ; 3. 79 (3H, s) ; 3. 98 (2H, s) ; 7. 29 (lH, dd) ; 7. 47 (lH, s) ; 7. 53 (lH, d) ; 7. 64 (lH, d) ; 8. 13 (lH, br) 24 1. 02 (6H, s) ; 1. 21 (3H, t) ; 2. 51 (3H, s) ; 2. 9 (2H, s) ; 2. 98 (lH, m) ; 3. 4 (2H, d) ; 3. 6 (2H, q) ; 3. 7 (2H, br) ; 5. 1 (2H, br) ; 7. 05 (lH, br) ; 7. 4 (2H, br) 25 152-153 2. 38 (3H, s) ; 3. 98 (2H, s) ; 4. 32 (2H, s) ; 7. 28 (lH, dd) ; 7. 48 (9H, m) ; 7. 66 (lH, d) ; 8. 09 (lH, br) 26 1. 2 (7H, m) ; 1. 5 (4H, m) ; 2. 09 (2H, m) ; 2. 25 (lH, br) ; 2. 5 (3H, s) ; 2. 7-2. 85 (2H, m) ; 3. 6 (2H, q) ; 3. 7 (2H, br) ; 5. 1 (2H, br) ; 7. 05 (lH, br) ; 7. 38 (2H, br) 27 l. l (3H, t) ; 1. 2 (3H, t) ; 1. 25 (2H, m) ; 1. 6 (4H, m) ; 1. 9 (1H, m) ; 2. 25 (lH, m) ; 2. 5 (3H, s) ; 3. 18 (lH, m) ; 3. 45 (2H, m) ; 3. 6 (2H, q) ; 3. 7 (2H, br) ; 3. 82 (2H, m) ; 5. 1 (2H, br) ; 7. 05 (1H, br) ; 7. 4 (2H, br) TABLE 2 Continued 28 1. 19 (3H, t) ; 1. 45 (2H, m) ; 1. 8 (2H, m) ; 2. 5 (3H, s) ; 3. 57 (2H, q) ; 3. 68 (2H, br) ; 5. 05 (2H, br) ; 7. 0 (lH, br) ; 7. 35 (6H, m) 29 1. 09 (9H, s) ; 2. 50 (3H, s) ; 2. 81 (2H, s) ; 3. 68 (2H, s) ; 5. 64 (2H, s) ; 6. 90-7. 09 (4H, m) ; 7. 21-7. 31 (2H, m) ; 7. 31-7. 41 (2H, m) 30 1. 37 (3H, s) ; 1. 45 (3H, s) ; 2. 38 (3H, s) ; 2. 41 (lH, t) ; 2. 58 (lH, d) ; 3. 99 (2H, s) ; 7. 17 (lH, d) ; 7. 29 (lH, dd) ; 7. 52 (lH, d) ; 7. 64 (lH, d) ; 8. 16 (lH, s) 31 1. 33 (3H, s) ; 1. 40 (3H, s) ; 2. 29 (lH, t) ; 2. 39 (3H, s) ; 2. 43 (lH, d) ; 3. 99 (2H, s) ; 6. 47 (lH, d) ; 7. 27 (lH, dd) ; 7. 52 (lH, d) ; 7. 64 (lH, d) ; 8. 14 (lH, s) 32 159. 7-165. 7 1. 30 (3H, s) ; 1. 32 (3H, s) ; 2. 19 (lH, d) ; 2. 37 (3H, s) ; 2. 58 (lH, dd) ; 3. 99 (2H, s) ; 5. 76 (lH, d) ; 7. 26 (lH, dd) ; 7. 51 (lH, d) ; 7. 61 (lH, d) ; 8. 35 (lH, d) 33 1. 34 (3H, s) ; 1. 41 (3H, s) ; 2. 38 (1H, t) ; 2. 38 (3H, s) ; 2. 50 (1H, d) ; 3. 98 (2H, s) ; 6. 31 (1H, dd) ; 7. 27 (1H, dd) ; 7. 52 (1H, d) ; 7. 63 (lH, d) ; 8. 20 (lH, s) 34 118. 7-124. 1 1. 30 (3H, s) ; 1. 39 (3H, s) ; 1. 79 (lH, m) ; 2. 28 (lH, d) ; 2. 38 (3H, s) ; 2. 89 (2H, m) ; 3. 98 (2H, s) ; 7. 24 (1H, dd) ; 7. 51 (1H, d) ; 7. 61 (1H, d) ; 8. 20 (lH, s) 35 1. 34 (3H, s) ; 1. 40 (3H, s) ; 2. 38 (3H, s) ; 2. 49 (1H, d) ; 2. 81 (1H, m) ; 3. 99 (2H, s) ; 6. 50 (1H, d) ; 7. 29 (1H, dd) ; 7. 54 (1H, d) ; 7. 64 (lH, d) ; 8. 23 (1H, s) 36 59. 8-61. 7 1. 28 (3H, s) ; 1. 48 (3H, s) ; 2. 38 (3H, s) ; 2. 38 (in, t) ; 2. 46 (lH, d) ; 3. 99 (2H, s) ; 7. 29 (lH, dd) ; 7. 52 (lH, d) ; 7. 62 (1H, d) ; 8. 20 (1H, s) 37 104. 1-105. 6 1. 20 (3H, t) ; 1. 31 (3H, s) ; 1. 39 (3H, s) ; 2. 45 (1H, d) ; 2. 51 (3H, s) ; 2. 79 (1H, t) ; 3. 61 (2H, q) ; 3. 70 (2H, s) ; 5. 10 (2H, s) ; 6. 49 (1H, d) ; 7. 07 (1H, d) ; 7. 39 (1H, s) ; 7. 40 (1H, d) 38 1. 20 (3H, t) ; 1. 28 (3H, s) ; 1. 30 (3H, s) ; 2. 16 (1H, d) ; 2. 51 (3H, s) ; 2. 54 (lH, dd) ; 3. 60 (2H, q) ; 3. 70 (2H, s) ; 5. 10 (2H, s) ; 5. 75 (1H, d) ; 7. 03 (1H, d) ; 7. 38 (lH, d) ; 7. 39 (1H, s) 39 1. 20 (3H, t) ; 1. 25 (3H, s) ; 1. 46 (3H, s) ; 2. 36 (1H, dd) ; 2. 42 (1H, d) ; 2. 51 (3H, s) ; 3. 61 (2H, q) ; 3. 70 (2H, s) ; 5. 09 (2H, s) ; 7. 07 (1H, d) ; 7. 38 (1H, s) ; 7. 39 (1H, d)

The compounds of the invention may be made in a variety of ways.

A compound of formula (I) wherein Y is oxygen, R57 is H and may be prepared by acylating a compound of formula (IT) wherein Rl and Rl2 are as defined in relation to formula (I) with a compound of formula (III) wherein q, B, Z and R58 are as defined in

relation to formula (I), preferably in the presence of a known coupling agent such as 1, 3- dicyclohexylcarbodiimide, 1, 3-diisopropylcarbodiimide or 1- (3-dimethylaminopropyl)-3- ethylcarbodiimide. Alternatively a compound of formula (III) may first be converted to an acid chloride or anhydride suitable for reaction with an amine to form an amide ; such procedures are well known and are described, for example, in J. March, Advanced Organic Chemistry, Third Edition, John Wiley and Sons, New York, 1985, pages 370-376 and references therein.

Compounds of formula (II) are either known compounds or may be prepared from known starting materials by methods described in the literature (see, for example, C.

Oliver Kappe, Robert Flammang, and Curt Wentrup, Heterocycles, Vol. 37, No. 3, 1615, (1994) ; A. Adams and R. Slack, J. Chem. Soc., 3061, (1959) ; and Ronald E Hackler, Kenneth W. Burow, Jr., Sylvester V. Kaster and David I. Wickiser, J. Heterocyclic Chem, 26, 1575, (1989)).

A compound of formula (HI) may be prepared by hydrolysis of the corresponding compound of formula (IV) (wherein q, B, Z, and R58 are as defined in relation to formula (I) and R is optionally substituted C1~6 alkyl) by methods known in the art. R is selected such that hydrolysis leaves the remainder of the molecule unchanged ; such a selection may be made for example, by reference to Theodora W. Greene, Protective Groups in Organic Synthesis, Chapter 5, John Wiley and Sons, New York, 1981.

A compound of formula (IV) may be prepared from a compound of formula (V) wherein q and Z are as defined in relation to formula (I), R is optionally substituted Cl 6 alkyl, and Q is a suitable precursor (atom or group) for the formation of the desired ring under conditions described in the literature (see, for example, David W. Dunwell, Delme Evans, Terence A. Hicks, J. Med. Chem., 1975, Vol. 18, No. 1, 53 ; Abdou O.

Abdelhamid, Cyril Parkanyi, S. M. Khaledur Rashid and Winston D. Lloyd, J.

Heterocyclic Chem., 25, 403, (1988) ; Teruyuki Kondo, Sungbong Yang, Keun-Tae Huh, Masanobu Kobayashi, Shinju Kotachi and Yoshihisa Watanabe, Chemistry Letters, 1275- 1278, 1991 ; Dale L. Boger, J. Org. Chem., 43, No 11, 2296, 1978). Thus a compound of formula (IV) wherein B is N may be made from a compound of formula (V) wherein Q is NH2, and a compound of formula (IV) wherein B is CR8 may be made from a compound

of formula (V) wherein Q is iodine or bromine by known methods. The substituent R58 may be an atom or group which itself may be converted into other functional groups ; procedures are known in the literature for such transformations involving benzoxazoles and benzothiazoles (for example, Lazer, Edward S., Adams, Julian ; Miao, Clara K. ; Farina, Peter, Eur. Pat. Appl. EP0535521). Alternatively R58 may contain atoms or groups which may be replaced by other moieties under known conditions.

A compound of formula (V) wherein Q is NH2 may be prepared by reduction of a compound of formula (VI) wherein q and Z are as defined in relation to formula (I) and R is optionally substituted C1~6 alkyl and such procedures are known in the art (see, for example, J. March, Advanced Organic Chemistry, Third Edition, John Wiley and Sons, New York, 1985, and references therein). A compound of formula (VI), wherein Z is oxygen, may be prepared by the nitration of a compound of formula (VII) (wherein q is as defined in relation to formula (I) Z is oxygen and R is optionally substituted CI~6 alkyl) under known conditions. A compound of formula (VI) (wherein Z is sulfur) may be prepared from a compound of formula (VI) (wherein Z is oxygen) using conditions similar to those described by J. Scheigetz, R. Zamboni and B. Roy, Synth. Commun., 25 (1995) (18), pages 2791-2806. A compound of formula (VI) (wherein Z is Nu 14 and R is H) may be prepared from a compound of formula (VII) by a sequence of acylation, nitration and deacylation ; using conditions known in the art. A compound of formula (VI) (wherein Z is NRI4 and R is optionally substituted Cl 6 alkyl) may be prepared from a compound of formula (VI) wherein Z is Nu 14 and R is H by known methods A compound of formula (V), wherein Z is oxygen or NRl4 and Q is bromine or iodine may be prepared from a compound of formula (VII) by halogenation (bromination or iodination respectively) under known conditions Compounds of formula (VII) wherein Z is oxygen or Nui4, R is optionally substituted CI-6 alkyl and q is 0 or 1 are either known compounds or may be made from known materials by known methods.

Alternatively, a compound of formula (I) wherein Y is oxygen, Z is oxygen and R57 is H may be prepared by treating a compound of formula (VIII) wherein q, Rl and Rl2 are as defined in relation to formula (I) with, for example, an acid in the presence of a

coupling reagent, an orthoester, acid chloride, anhydride, hydroxyimoyl chloride or an alcohol in the presence of a ruthenium catalyst as described previously for the preparation of a compound of formula (IV).

A compound of formula (VIII) may be obtained by reduction of a compound of formula (IX) wherein q, R'and R12 are as defined in relation to formula (I), itself obtained from a compound of formula (X) wherein q, Rl and Rl2 are as defined in relation to formula (I) using the procedures described above for the transformation of a compound of formula (VII) to a compound of formula (V).

A compound of formula (X) may be obtained by reacting a compound of formula (XI) (wherein q, Rl, and R12 are as defined in relation to formula (I)) with a suitable reagent such as boron tribromide, hydriodic acid or another suitable reagent, as described by Theodora W. Greene, Protective Groups in Organic Synthesis, Chapter 1, John Wiley and Sons, New York, 1981.

A compound of formula (XI) may be prepared by coupling a compound of formula (II) with a compound of formula (XII) (wherein q is as defined in relation to formula (I)) in a manner analogous to that described above for the transformation of a compound of formula (m) to a compound of formula (I).

Compounds of formula (XII) are known compounds or may be prepared from known compounds by known methods.

In a further approach, a compound of formula (IX) may be prepared by coupling a compound of formula (II) with a compound of formula (VI) (wherein R is H) in a manner analogous to that described above for the transformation of a compound of formula (III) to a compound of formula (I) An alternative method for preparing a compound of formula (IV) (wherein Z is sulfur) involves the cyclisation of a compound of formula (XIII) (wherein LG is a halogen, such as fluorine, chlorine or bromine and wherein q and R58 are as defined in relation to formula (I) and R is optionally substituted C, ~6 alkyl) as described, for example, in Comprehensive Heterocyclic Chemistry, Volume 6, Ed. Katritzky and Rees, Pergamon Press, 1984. A compound of formula (XIII) may be prepared by reacting a compound of formula (XIV) (wherein LG is a halogen, such as fluorine, chlorine or

bromine and wherein q and R58 are as defined in relation to formula (I) and R is optionally substituted C1~6 alkyl) with a suitable thionating agent such as 2, 4-bis (4- methoxyphenyl)-1, 3-dithia-2, 4-diphosphetane-2, 4-disulfide (Lawesson's reagent), 2, 4- bis (methylthio)-1, 3-dithia-2, 4-diphosphetane-2, 4-disulfide (Davy reagent methyl), 2, 4- bis (para-tolyl)-1, 3-dithia-2, 4-diphosphetane-2, 4-disulfide (Davy reagentp-tolyl) or phosphorus pentasulfide in a suitable solvent such as toluene or fluorobenzene. A compound of formula (XIV) may be derived from a compound of formula (XV) (wherein LG is a halogen, such as fluorine, chlorine or bromine and wherein q is as defined in relation to formula (I) and R is H) by nitration followed by esterification of the resultant nitrobenzene compound, reduction of the resultant nitrohalobenzene compound and subsequent acylation of the resultant aminohalobenzene compound, using procedures well known to those skilled in the art.

Compounds of formula (XV) are known compounds or may be made from known materials using known methods.

A compound of formula (in) (wherein R58 is as defined in relation to formula (I), q is zero, Z is oxygen or sulfur and B is nitrogen) may also be prepared by halogenation of a compound of formula (XVI) (wherein R58 is as defined in relation to formula (I), and Z is oxygen or sulfur) followed by displacement of the resultant compound of formula (XVII) (where Hal is chloro or bromo, Z is oxygen or sulfur and R58 is as defined in relation to formula (I)) with cyanide. Hydrolysis of the resultant compound of formula (XVE) (wherein R58 is as defined in relation to formula (I) and Z is oxygen or sulfur) gives a compound of formula (III) wherein R58 is as defined in relation to formula (1), q is zero, Z is oxygen or sulfur and B is nitrogen.

Treatment of a compound of formula (I) (wherein R57 is hydrogen and Y is oxygen) with an alkylating or acylating agent, optionally in the presence of a base and a phase transfer catalyst, provides a compound of formula (I), wherein R57 is an alkyl or acyl group and Y is oxygen. Examples of suitable alkylating agents include, but are not restricted to, alkyl halides (such as methyl iodide), haloalkyl ethers (such as chloromethyl ethyl ether) and alkyl sulfates (such as dimethylsulfate). Suitable acylating agents include anhydrides (such as acetic anhydride), acid chlorides (such as acetyl chloride or benzoyl

chloride) and chloroformates (such as ethyl chloroformate). Suitable bases include organic bases (such as triethylamine or pyridine), alkali metal alkoxides (such as potassium tert-butoxide) and inorganic bases (such as sodium hydride or sodium hydroxide). Suitable phase transfer catalysts may be selected by reference to the literature (see, for example, J. March, Advanced Organic Chemistry, Third Edition, John Wiley and Sons, New York, 1985, pages 320-322 and references therein).

In a further approach, a compound of formula (IV) wherein B, Z and R58 are as defined in relation to formula (I) and q is 1 may be prepared by treating a compound of formula (XIX) wherein B, Z and R58 are as defined in relation to formula (I) and q is 1 with an optionally substituted haloalkyl ester preferably in the presence of a base such as potassium carbonate. Similarly, a compound of formula (XX) wherein Z, B and R58 are as defined in relation to formula (I) and halo is chloro or, especially, bromo or iodo can be reacted with an appropriate malonate derivative in the presence of suitable catalysts, for example palladium (0) derivatives, to give a compound of formula (IV) wherein B, Z and R58 are as defined in relation to formula (I) and q is 0.

A compound of formula (I) (wherein Y is sulfur) may be prepared by reacting a compound of formula (I) (where Y is oxygen) with a suitable thionating agent such as 2, 4-bis (4-methoxyphenyl)-1, 3-dithia-2, 4-diphosphetane-2, 4-disulfide (Lawesson's reagent), 2, 4-bis (methylthio)-1, 3-dithia-2, 4-diphosphetane-2, 4-disulfide (Davy reagent methyl), 2, 4-bis (para-tolyl)-1, 3-dithia-2, 4-diphosphetane-2, 4-disulfide (Davy reagent- tolyl) or phosphorus pentasulfide in a suitable solvent such as toluene or fluorobenzene.

A compound of formula (I) (wherein Y is sulfur and R57 is H) may be treated with an electrophile (such as an alkyl halide, dialkyl sulfate or trialkyloxonium salt) optionally in the presence of a base to give a compound of formula (XXI) (wherein Y is sulfur and R is alkyl, alkenylalkyl, alkynylalkyl, cycloalkyl, alkoxyalkyl) Such a compound may be further treated with a compound of formula Rl3-NH2 (where R13 is as defined above for a compound of formula (I)) optionally in the presence of a mercuric salt (such as mercuric chloride), according to known procedures to give a compound of formula (I) wherein R57 is H and Y is NR. Such a compound may be treated with an alkylating agent, an

acylating agent or similar electrophile to give a compound of formula (1) [where R57 is as defined above for a compound of formula (I) (except that R57 is not H) and Y is NR13].

Chemical Formulae (t) ('a) (IV) (V)

The compounds of formula (I) can be used to combat and control infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and Isoptera and also other invertebrate pests, for example, acarine, nematode and mollusc pests. Insects, acarines, nematodes and molluscs are hereinafter collectively referred to as pests. The pests which may be combated and controlled by the use of the invention compounds include those pests associated with agriculture (which term includes the growing of crops for food and fibre products), horticulture and animal husbandry, companion animals, forestry and the storage of products of vegetable origin (such as fruit, grain and timber) ; those pests associated with the damage of man-made structures and the transmission of diseases of man and animals ; and also nuisance pests (such as flies).

Examples of pest species which may be controlled by the compounds of formula (I) include : Myzus persicae (aphid), Aphis gossypii (aphid), Aphisfabae (aphid), Lygus spp.

(capsids), Dysdercus spp. (capsids), Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper), Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp.

(stinkbugs), Frankliniella occidentalis (thrip), Thrips spp. (thrips), Leptinotarsa decemlineata (Colorado potato beetle), Anthonomus grandis (boll weevil), Aonidiella spp.

(scale insects), Trialeurodes spp. (white flies), Bemisia tabaci (white fly), Ostrinia nubilalis (European corn borer), Spodoptera littoralis (cotton leafworm), Heliothis nirescens (tobacco budworm), Helicoverpa armigera (cotton bollworm), Helicoverpa zea (cotton bollworm), Sylepta derogata (cotton leaf roller), Pieris brassicae (white butterfly), Plutella xylostella (diamond back moth), Agrotis spp. (cutworms), Cliilo suppressalis (rice stem borer), Locusta~ rnigratoria (locust), Chortiocetes terminifera (locust), Diabrotica spp. (rootworms), Panonyclilis ulini (European red mite), Panonychus citri (citrus red mite), Tetranychus urticale (two-spotted spider mite), Tetranychus cinnabarinus (carmine spider mite), Phvllocoptruta oleivora (citrus rust mite), Polyphagotarsonemus latus (broad mite), Brevipalpus spp. (flat mites), Boophilus microplus (cattle tick), Dermacentor variabilis (American dog tick), Ctenocephalidesfelis (cat flea), Liriomyza spp. (leafminer), Musca domestica (housefly), Aedes aegypti (mosquito), Anopheles spp. (mosquitoes), Culex spp.

(mosquitoes), Lucillia spp. (blowflies), Blattella gerinanica (cockroach), Periplaneta aryiericanca (cockroach), Blatta orientalis (cockroach), termites of the Mastotermitidae (for example Mastotermes spp.), the Kalotermitidae (for example Neotern7es spp.), the

Rhinotermitidae (for example Coptotermesformosanus, Reticulitermesflavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis) and the Termitidae (for example Globitermes sulphureus), Solenopsis geminata (fire ant), Monomorium pharaonis (pharaoh's ant), Damalinia spp. and Linognathus spp. (biting and sucking lice), Meloidogyne spp. (root knot nematodes), Globodera spp. and Heterodera spp. (cyst nematodes), Pratylenchus spp.

(lesion nematodes), Rhodopholus spp. (banana burrowing nematodes), Tylenchulus spp. (citrus nematodes), Haemonchus contorts (barber pole worm), Caenorhabditis elegans (vinegar eelworm), Trichostrongylus spp. (gastro intestinal nematodes) and Deroceras retictilatum (slug).

The compounds of formula (I) are also active fungicides and may be used to control one or more of the following pathogens : Pyricularia oryzae (Magnaporthe grisea) on rice and wheat and other Pyricularia spp. on other hosts ; Puccinia recondita, Puccinia striiformis and other rusts on wheat, Puccinia hordei, Puccinia striiformis and other rusts on barley, and rusts on other hosts (for example turf, rye, coffee, pears, apples, peanuts, sugar beet, vegetables and ornamental plants) ; Erysiphe cichoracearum on cucurbits (for example melon) ; Erysiphe graminis (powdery mildew) on barley, wheat, rye and turf and other powdery mildews on various hosts, such as Sphaerotheca maculais on hops, Sphaerotheca fusca (Sphaerothecafuliginea) on cucurbits (for example cucumber), Leveillula taurica on tomatoes, aubergine and green pepper, Podosphaera leucotricha on apples and Uncinula necator on vines ; Cochliobolus spp., Helminthosporium spp., Drechslera spp. (Pyrenophora spp.), Rhynchosporium spp., Mycosphaerella graminicola (Septoria tritici) and Phaeosphaeria nodorum (Stagonospora nodorum or Septoria nodorum), Pseudocercosporella herpotrichoides and Gaeumannomyces graminis on cereals (for example wheat, barley, rye), turf and other hosts ; Cercospora arachidicola and Cercosporidium personatum on peanuts and other Cercospora spp. on other hosts, for example sugar beet, bananas, soya beans and rice ; Botrytis cinerea (grey mould) on tomatoes, strawberries, vegetables, vines and other hosts and other Botrytis spp. on other hosts ; Alternaria spp. on vegetables (for example carrots), oil-seed rape, apples, tomatoes, potatoes, cereals (for example wheat) and other hosts ; Venturia spp. (including Venturia inaequalis (scab)) on apples, pears, stone fruit, tree nuts and other hosts ; Cladosporium spp. on a range of hosts including cereals (for example wheat) and tomatoes ; Monilinia spp. on stone fruit, tree nuts and other hosts ; Didvniella spp. on tomatoes, turf, wheat, cucurbits and other hosts ; Phoma spp. on oil-seed rape, turf, rice, potatoes, wheat and other hosts ; Aspergillus spp. and

Aureobasidium spp. on wheat, lumber and other hosts ; Ascochyta spp. on peas, wheat, barley and other hosts ; Stemphylium spp. (Pleospora spp.) on apples, pears, onions and other hosts ; summer diseases (for example bitter rot (Glomerella cingulata), black rot or frogeye leaf spot (Botryosphaeria obtusa), Brooks fruit spot (Mycosphaerella pomi), Cedar apple rust (Gymnosporangium juniperi-virginianae), sooty blotch (Gloeodes pomigena), flyspeck (Schizothyrium pomi) and white rot (Botryosphaeria dothidea)) on apples and pears ; Plasmopara viticola on vines ; other downy mildews, such as Bremia lactucae on lettuce, Peronospora spp. on soybeans, tobacco, onions and other hosts, Pseudoperonospora humuli on hops and Pseudoperonospora cubensis on cucurbits ; Pythium spp. (including Pythium ultimum) on turf and other hosts ; Phytophthora infestans on potatoes and tomatoes and other Phytophthora spp. on vegetables, strawberries, avocado, pepper, ornamentals, tobacco, cocoa and other hosts ; Thanatephorus cucumeris on rice and turf and other Rhizoctonia spp. on various hosts such as wheat and barley, peanuts, vegetables, cotton and turf ; Sclerotinia spp. on turf, peanuts, potatoes, oil-seed rape and other hosts ; Sclerotium spp. on turf, peanuts and other hosts ; Gibberellafujikuroi on rice ; Colletotrichum spp. on a range of hosts including turf, coffee and vegetables ; Laetisariafuciformis on turf ; Mycosphaerella spp. on bananas, peanuts, citrus, pecans, papaya and other hosts ; Diaporthe spp. on citrus, soybean, melon, pears, lupin and other hosts ; Elsinoe spp. on citrus, vines, olives, pecans, roses and other hosts ; Verticillium spp. on a range of hosts including hops, potatoes and tomatoes ; Pyrenopeziza spp. on oil-seed rape and other hosts ; Oncobasidium theobromae on cocoa causing vascular streak dieback ; Fusarium spp., Typhula spp., Microdochium nivale, Ustilago spp., Urocystis spp., Tilletia spp. and Claviceps purpurea on a variety of hosts but particularly wheat, barley, turf and maize ; Ramularia spp. on sugar beet, barley and other hosts ; post-harvest diseases particularly of fruit (for example Penicillium digitatum, Penicillium italicum and Trichoderma viride on oranges, Colletotrichum musae and Gloeosporium musarum on bananas and Botrytis cinerea on grapes) ; other pathogens on vines, notably Eutypa lata, Guignardia bidwellii, Phellinus igniarus, Phomopsis viticola, Pseudopeziza tracheiphila and Stereum hirsutum ; other pathogens on trees (for example Lophodermium seditiosum) or lumber, notably Cephaloascus fragrans, Ceratocystis spp., Ophiostoma piceae, Penicilium spp., Trichoderma pseudokoningii, Trichoderma viride, Trichoderma harzianum, Aspergillus niger, Leptographium lindbergi and Aureobasidium pullulans ; and fungal vectors of viral diseases (for example Polymyxa graminis on cereals as

the vector of barley yellow mosaic virus (BYMV) and Polymyxa betae on sugar beet as the vector of rhizomania).

A compound of formula (I) may move acropetally, basipetally or locally in plant tissue to be active against one or more fungi. Moreover, a compound of formula (I) may be volatile enough to be active in the vapour phase against one or more fungi on the plant.

The invention therefore provides a method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a pest, a locus of pest, or to a plant susceptible to attack by a pest, and a method of combating and controlling fungi which comprises applying a fungicidally effective amount of a compound of formula (I), or a composition containing a compound of formula (I), to a plant, to a seed of a plant, to the locus of the plant or seed, to soil or to any other growth medium (for example a nutrient solution). The compounds of formula (I) are preferably used against insects, acarines, nematodes or fungi.

The term"plant"as used herein includes seedlings, bushes and trees. Furthermore, the fungicidal method of the invention includes protectant, curative, systemic, eradicant and antisporulant treatments.

As fungicides, the compounds of formula (I) are preferably used for agricultural, horticultural and turfgrass purposes in the form of a composition.

In order to apply a compound of formula (1) as an insecticide, acaricide, nematicide or molluscicide to a pest, a locus of pest, or to a plant susceptible to attack by a pest, or, as a fungicide to a plant, to a seed of a plant, to the locus of the plant or seed, to soil or to any other growth medium, a compound of formula (I) is usually formulated into a composition which includes, in addition to the compound of formula (I), a suitable inert diluent or carrier and, optionally, a surface active agent (SFA). SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0. 0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of a compound of formula (I). The composition is generally used for the control of pests or fungi such that a compound of formula (I) is applied at a rate

of from 0. 1 g to l Okg per hectare, preferably from I g to 6kg per hectare, more preferably from lg to lkg per hectare.

When used in a seed dressing, a compound of formula (I) is used at a rate of O. 0001 g to lOg (for example O. OOlg or O. 05g), preferably O. 005g to lOg, more preferably O. 005g to 4g, per kilogram of seed.

In another aspect the present invention provides an insecticidal, acaricidal, nematicidal, molluscicidal or fungicidal composition comprising an insecticidally, acaricidally, nematicidally, molluscicidally or fungicidally effective amount of a compound of formula (1) and a suitable carrier or diluent therefor. The composition is preferably an insecticidal, acaricidal, nematicidal or fungicidal composition.

In a still further aspect the invention provides a method of combating and controlling pests or fungi at a locus which comprises treating the pests or fungi or the locus of the pests or fungi with an insecticidally, acaricidally, nematicidally, molluscicidally or fungicidally effective amount of a composition comprising a compound of formula (I). The compounds of formula (I) are preferably used against insects, acarines, nematodes or fungi.

The compositions can be chosen from a number of formulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke formulations, capsule suspensions (CS) and seed treatment formulations. The formulation type chosen in any instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of formula (I).

Dustable powders (DP) may be prepared by mixing a compound of formula (I) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of formula (1) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulphate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of

said agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of formula (I) with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or from pre-formed blank granules by absorbing a compound of formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compound of formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallisation in a spray tank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200 ; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethyl amides of fatty acids (such as Cs-C I o fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with

sufficient stability to allow spray application through appropriate equipment. Preparation of an EW involves obtaining a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifiying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of formula (I) is present initially in either the water or the solvent/SFA blend. Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs. An ME may be either an oil-in-water or a water-in-oil system (which system is present may be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. An ME is suitable for dilution into water, either remaining as a microemulsion or forming a conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of formula (I). SCs may be prepared by ball or bead milling the solid compound of formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension of the compound.

One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of formula (I) may be dry milled and added to water, containing agents hereinbefore described, to produce the desired end product.

Aerosol formulations comprise a compound of formula (I) and a suitable propellant (for example n-butane). A compound of formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps.

A compound of formula (I) may be mixed in the dry state with a pyrotechnic mixture to form a composition suitable for generating, in an enclosed space, a smoke containing the compound.

Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerisation stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of formula (1) and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of formula (1) and they may be used for seed treatment. A compound of formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.

A composition may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces ; resistance to rain on treated surfaces ; or uptake or mobility of a compound of formula (I)). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of formula (I)).

A compound of formula (I) may also be formulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS, SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-forming barrier).

Wetting agents, dispersing agents and emulsifying agents may be surface SFAs of the cationic, anionic, amphoteric or non-ionic type.

Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts.

Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di- isopropyl-and tri-isopropyl-naphthalene sulphonates), ether sulphates, alcohol ether

sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid ; additionally these products may be ethoxylated), sulphosuccinamates, paraffin or olefine sulphonates, taurates and lignosulphonates.

Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.

Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol) ; partial esters derived from long chain fatty acids or hexitol anhydrides ; condensation products of said partial esters with ethylene oxide ; block polymers (comprising ethylene oxide and propylene oxide) ; alkanolamides ; simple esters (for example fatty acid polyethylene glycol esters) ; amine oxides (for example lauryl dimethyl amine oxide) ; and lecithins.

Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite).

A compound of formula (I) may be applied by any of the known means of applying pesticidal or fungicidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.

A compound of formula (I) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.

Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the form of a concentrate containing a high proportion of the active

ingredient, the concentrate being added to water before use. These concentrates, which may include DCs, SCs, ECs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are often required to withstand storage for prolonged periods and, after such storage, to be capable of addition to water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may contain varying amounts of a compound of formula (I) (for example 0. 0001 to 10%, by weight) depending upon the purpose for which they are to be used.

A compound of formula (I) may be used in mixtures with fertilisers (for example nitrogen-, potassium-or phosphorus-containing fertilisers). Suitable formulation types include granules of fertiliser. The mixtures suitably contain up to 25% by weight of the compound of formula (I).

The invention therefore also provides a fertiliser composition comprising a fertiliser and a compound of formula (I).

The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having similar or complementary fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.

By including another fungicide, the resulting composition may have a broader spectrum of activity or a greater level of intrinsic activity than the compound of formula (I) alone. Further the other fungicide may have a synergistic effect on the fungicidal activity of the compound of formula (I).

The compound of formula (I) may be the sole active ingredient of the composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An additional active ingredient may : provide a composition having a broader spectrum of activity or increased persistence at a locus ; synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of formula (I) ; or help to overcome or prevent the development of resistance to individual components. The particular additional active ingredient will depend upon the intended utility of the composition. Examples of suitable pesticides include the following : a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin,

s-bioallethrin, fenfluthrin, prallethrin or 5-benzyl-3-furylmethyl-(0-(1 R, 3S)-2, 2-dimethyl- 3- (2-oxothiolan-3-ylidenemethyl) cyclopropane carboxylate ; b) Organophosphates, such as, profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon ; c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur, methomyl or oxamyl ; d) Benzoyl ureas, such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron or chlorfluazuron ; e) Organic tin compounds, such as cyhexatin, fenbutatin oxide or azocyclotin ; f) Pyrazoles, such as tebufenpyrad and fenpyroximate ; g) Macrolides, such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad or azadirachtin ; h) Hormones or pheromones ; i) Organochlorine compounds such as endosulfan, benzene hexachloride, DDT, chlordane or dieldrin ; j) Amidines, such as chlordimeform or amitraz ; k) Fumigant agents, such as chloropicrin, dichloropropane, methyl bromide or metam ; 1) Chloronicotinyl compounds such as imidacloprid, thiacloprid, acetamiprid, nitenpyram or thiamethoxam ; m) Diacylhydrazines, such as tebufenozide, chromafenozide or methoxyfenozide ; n) Diphenyl ethers, such as diofenolan or pyriproxifen ; o) Indoxacarb ; p) Chlorfenapyr ; or q) Pymetrozine.

In addition to the major chemical classes of pesticide listed above, other pesticides having particular targets may be employed in the composition, if appropriate for the intended utility of the composition. For instance, selective insecticides for particular crops, for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed. Alternatively insecticides or acaricides

specific for particular insect species/stages may also be included in the compositions (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon ; acaricidal motilicides, such as dicofol or propargite ; acaricides, such as bromopropylate or chlorobenzilate ; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).

Examples of fungicidal compounds which may be included in the composition of the invention are (E)-N-methyl-2- [2- (2, 5-dimethylphenoxymethyl) phenyl]-2-methoxy- iminoacetamide (SSF-129), 4-bromo-2-cyano-N, N-dimethyl-6-trifluoromethylbenzimidazole- 1-sulphonamide, a- [N- (3-chloro-2, 6-xylyl)-2-methoxyacetamido]-y-butyrolactone, 4-chloro- 2-cyano-N, N-dimethyl-5-p-tolylimidazole-1-sulfonamide (IKF-916, cyamidazosulfamid), 3-5-dichloro-N- (3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH-7281, zoxamide), N-allyl-4, 5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide (MON65500), N- (1-cyano-1, 2-dimethylpropyl)-2- (2, 4-dichlorophenoxy) propionamide (AC382042), N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide, acibenzolar (CGA245704), alanycarb, aldimorph, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl, biloxazol, bitertanol, blasticidin S, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulphate, copper tallate and Bordeaux mixture, cymoxanil, cyproconazole, cyprodinil, debacarb, di-2-pyridyl disulphide 1, 1'-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, diflumetorim, O, O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride, dodemorph, dodine, doguadine, edifenphos, epoxiconazole, ethirimol, ethyl (Z)-N-benzyl-N ( [methyl (methyl-thioethylideneaminooxycarbonyl) amino] thio)- -p-alaninate, etridiazole, famoxadone, fenamidone (RPA407213), fenarimol, fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluoroimide, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanyl butyl carbamate, isoprothiolane, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil,

metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace, organomercury compounds, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, phenazin oxide, phosetyl-Al, phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxin D, polyram, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, propionic acid, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinomethionate, quinoxyfen, quintozene, sipconazole (F-155), sodium pentachlorophenate, spiroxamine, streptomycin, sulphur, tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifluzamid, 2- (thiocyanomethylthio) benzothiazole, thiophanate-methyl, thiram, timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, zineb and ziram.

The compounds of formula (1) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions include piperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in the compositions will depend upon the intended target and the effect required.

An example of a rice selective herbicide which may be included is propanil. An example of a plant growth regulator for use in cotton is PIXTM.

Some mixtures may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation.

The invention is illustrated by the following Examples :

EXAMPLE 1 This Example illustrates the preparation of of N- (4-chloro-3-methylisothiazol-5- yl)-3-amino-4-hydroxyphenylacetamide.

Step 1-Preparation of 5-amino-4-chloro-3-methylisothiazole.

5-Amino-3-methylisothiazole hydrochloride (250g, 1. 66mole) was suspended in dichloromethane (1. 251) and stirred at 8°C. Sulfuryl chloride (146. 8ml, 1. 83mole) was added dropwise over lhour and during this addition the temperature of the reaction mixture was maintained between 10 and 15°C. As the sulfuryl chloride was added the suspension dissolved and a dark oil began to fall out of solution. The resultant two-phase mixture was stirred at 10°C for 15minutes. The mixture was cooled to below 10°C and quenched by careful addition of aqueous potassium carbonate solution (367. 3g, 2. 66mole of potassium carbonate in 11 of water). The two phases were separated and the aqueous layer was extracted with dichloromethane (600ml+400ml). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was slurried in hexane (ca. 500ml) for lhour, filtered and dried to give 5-amino-4- chloro-3-methylisothiazole as a red-brown-solid (228. 7g, 93%), m. p. 69-71°C.

1 H NMR (CDCl3) 8 : 2. 30 (3H, s) ; 4. 6 (2H, br) ppm.

Step 2-Preparation of methyl (4-hydroxyphenyl) acetate.

A solution of hydrogen chloride in methanol (ca. 20g of hydrogen chloride in 100ml of methanol) was introduced over a period of ca. 10minutes to a mixture of (4-hydroxyphenyl) acetic acid (3000g, 19. 7mole) in methanol (91) at 15-20°C. Stirring was continued for 3hours and the solvent was evaporated in vacuo to afford methyl (4- hydroxyphenyl) acetate as a light brown oil (3280g) which gradually solidified on standing.

'H NMR (CDC13) 8 : 3. 5 (2H, s) ; 3. 71 (3H, s) ; 6. 0 (lH, br) ; 6. 76 (2H, m) ; 7. 10 (2H, m) ppm.

Step 3-Preparation of methyl (4-hydroxy-3-nitrophenyl) acetate.

Acetic acid (151) and methyl (4-hydroxyphenyl) acetate (1540g, 9. 27mole) were sequentially charged, with stirring, to a 251 reactor and the solution was warmed to 24°C.

Approximately 30ml of nitric acid (69% by weight, 16M) was introduced and the system was monitored by gas chromatography. After 10minutes a slight exotherm was observed and gc analysis confirmed that the reaction had commenced. The remainder of the nitric acid (550ml) was then added at an even rate over a period of 2. 5hour, with cooling applied to maintain an internal temperature of ca. 24°C. The mixture was carefully quenched into water

(601) with vigorous stirring. An emulsion was formed which subsequently crystallised.

After filtration, washing with water and draining, the product was obtained in the form of a damp paste (2290g of ca. 70% by weight water wet paste) which could be dried further if required.

'H NMR (CDC13) 8 : 3. 63 (2H, s) ; 3. 72 (3H, s) ; 7. 14 (lH, d) ; 7. 52 (lH, dd) ; 8. 02 (lH, d) ; 10. 5 (lH, s) ppm.

Step 4-Preparation of 4-hydroxy-3-nitrophenylacetic acid.

Methyl 4-hydroxy-3-nitrophenylacetate (21. 1g, 0. 1mole) was suspended in a mixture of water (55ml) and methanol (105ml). The suspension was stirred at room temperature while a solution of sodium hydroxide (8. 8g, 0. 22mole) in water (50ml) was added dropwise over 20minutes, maintaining the reaction temperature between 20 and 25°C by water bath cooling. The resultant dark red solution was stirred at room temperature for 15minutes and was then diluted with water and acidified to pH 1-2 by addition of 2M hydrochloric acid.

The precipitate was collected by filtration. The filtrate was extracted with ethyl acetate, washed with brine (200ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to give a further quantity of desired product. 4-Hydroxy-3- nitrophenylacetic acid (combined yield 19. 6g) was obtained as a yellow solid.

'H NMR (CDC13) 6 : 7. 98 (lH, d) ; 7. 49 (lH, dd) ; 7. 07 (lH, d) ; 3. 55 (2H, s) ppm.

Step 5-Preparation of N- (4-chloro-3-methylisothiazol-5-yl)-4-hydroxy-3- nitrophenylacetamide.

4-Hydroxy-3-nitrophenylacetic acid (lOg, 0. 05mol) was suspended in dichloroethane (50ml) and stirred at room temperature under a nitrogen atmosphere. N, N-Dimethyl- formamide (0. lml) was added followed by dropwise additions of oxalyl chloride (6. 77g, 0. 05mole) over 20minutes. The mixture was stirred at room temperature for 25minutes and then at 40°C for 20minutes. The reaction was then heated under reflux while a solution of 5-amino-4-chloro-3-methylisothiazole (7. 54g, 0. 05mole) in dichloroethane (30ml) was added over 30minutes. The resultant pale orange suspension was stirred at reflux for 2hours and then cooled to room temperature. The resultant precipitate was collected by filtration and washed with dichloromethane. The solid was suspended in water (150ml), treated with 10% (by weight/volume) sodium hydroxide (50ml) and the resulting red solution was washed with dichloromethane (2x50ml). The combined washings were extracted with water (50ml) and the combined aqueous layers were acidified to pH 4-5 by addition of concentrated hydrochloric acid (ca. 10ml). The resultant yellow precipitate was collected by filtration and

the solid was washed with water and dried to give N- (4-chloro-3-methylisothiazol-5-yl)-4- hydroxy-3-nitrophenylacetamide (14. 6g) as a yellow solid.

1H NMR (d6-DMSO) 5 : 2. 3 (3H, s) ; 3. 9 (2H, s) ; 7. 05 (lH, d) ; 7. 4 (lH, dd) ; 7. 8 (lH, d) ; 10. 85 (lH, s) ; 11. 7 (lH, s) ppm.

Step 6-Preparation of N- (4-chloro-3-methylisothiazol-5-yl)-3-amino- 4- hydroxyphenylacetamide.

N- (4-chloro-3-methylisothiazol-5-yl)-4-hydroxy-3-nitrophenylac etamide (50g, 0. 153mole), 1% platinum on carbon (15g ; 44% water) andN, N-dimethylformamide (400ml) were charged to a 600ml stainless steel hydrogenation vessel. Once purged, the vessel was pressurised to 35bar with hydrogen, stirring was started and the reaction mixture was heated to 35°C. After 6hours the uptake of hydrogen had stopped ; the stirring and heating were turned off and the mixture was allowed to cool to ambient temperature. The reaction mixture was filtered to remove the catalyst and the filtrate was concentrated in vacuo. The residue was slurried in dichloromethane (300ml) for 10minutes, filtered, washed with dichloromethane (200ml) and dried to give N- (4-chloro-3-methylisothiazol-5-yl)-3-amino-4- hydroxyphenylacetamide (43. 9g, containing-4% wt/wt NN-dimethylformamide) as a buff solid, m. p. 239. 4-243. 4°C 1H NMR (d6-DMSO) 5 : 2. 25 (3H, s) ; 3. 62 (2H, s) ; 4. 63 (2H, br) ; 6. 29 (lH, dd) ; 6. 49 (1H, d) ; 6. 50 (lH, d) ; 8. 80 (lH, d) ; 11. 6 (lH, s) ppm.

EXAMPLE 2 This example illustrates the preparation of Compound 20, N- (4-chloro-3- methylisothiazol-5-yl)-[2-(2, 2-dimethyl-3-hydroxypropyl) benzoxazol-5-yl] acetamide and Compound 21, N- (4-chloro-3-methylisothiazol-5-yl)- [2- (2-formyl-2- methylpropyl) benzoxazol-5-yl] acetamide Step 1 Preparation of N- (4-chloro-3-methylisothiazol-5-yl)- [2- (2, 2-dimethyl-3- butenyl) benzoxazol-5-yl] acetamide Oxalyl chloride (5. 59 g, 0. 044 mol) was added dropwise, with stirring, to a mixture of 3, 3-Dimethyl-4-pentenoic acid (5. 12 g, 0. 04 mol) and N, N-dimethylformamide (two drops) in dichloromethane (40 ml) and the mixture stirred at room temperature for 2 hours.

Most of the solvent was removed in vacuo and the remaining solution (ca. 15 ml) was added dropwise to a mixture of N- (4-chloro-3-methylisothiazol-5-yl)-3-amino-4- hvdroxyphenylacetamide (11. 9 g, 0. 04 mol) and triethylamine (4. 04 g, 0. 04 mol) in N, N- dimethylacetamide (120 ml). The mixture was stirred at room temperature for 2 hours, then

poured onto a mixture of ice and water, and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo.

The residue was taken up in 1, 1, 2, 2-tetrachloroethane (200 ml), para-toluenesulfonic acid (5. 2 g, 0. 0275 mol) added and the mixture heated at 150 °C for 2 hours. The mixture was cooled to room temperature and the solvent evaporated in vacuo. The residue was partitioned between ethyl acetate and brine and the organic phase dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was further purified by column chromatography on silica gel, eluting with ethyl acetate : hexane 1 : 3 to give N- (4-chloro-3-methylisothiazol-5-yl)- [2- (2, 2-dimethyl-3-butenyl) benzoxazol-5- yl] acetamide (12. 6 g) as a viscous, orange residue which crystallised on standing.

'H NMR (CDC13) 8 : 1. 2 (6H, s) ; 2. 38 (3H, s) ; 2. 95 (2H, s) ; 3. 98 (2H, s) ; 5. 0 (2H, m) ; 5. 95 (lH, m) ; 7. 28 (lH, dd) ; 7. 53 (lH, d) ; 7. 63 (lH, d) ; 8. 18 (lH, br) ppm Step 2 Ozone was bubbled into a solution of N- (4-chloro-3-methylisothiazol-5-yl)- [2- (2, 2- dimethyl-3-butenyl) benzoxazol-5-yl] acetamide (1. 5 g, 0. 00385 mol) in methanol (45 ml) and dichloromethane (10 ml) at-78 °C until the solution became saturated. Sodium borohydride (0. 50 g, 0. 0135 mol) was added portionwise, and once the addition was complete the cooling bath was removed and the reaction mixture was allowed to warm to 0 °C. Acetone was added to destroy residual sodium borohydride and the solvent evaporated in vacuo. The residue was dissolved in a minimum quantity of water, neutralised and extracted with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting initially with ethyl acetate : hexane 1 : 1 to give N- (4- chloro-3-methylisothiazol-5-yl)- [2- (2-formyl-2-methylpropyl) benzoxazol-5-yl] acetamide (0. 392 g), m. p. 125-127 °C, and then with ethyl acetate : hexane 2 : 1 to give N- (4-chloro-3- methylisothiazol-5-yl)- [2- (2, 2-dimethyl-3-hydroxypropyl) benzoxazol-5-yl] acetamide (0. 078 g), m. p. 168-169 °C.

N- (4-chloro-3-methylisothiazol-5-yl)- [2- (2-formyl-2-methylpropyl) benzoxazol-5- yl] acetamide : IH NMR (CDC13) 8 : 1. 24 (6H, s) ; 2. 38 (3H, s) ; 3. 16 (2H, s) ; 3. 98 (2H, s) ; 7. 28 (lH, dd) ; 7. 52 (lH, d) ; 7. 62 (lH, d) ; 8. 18 (lH, br) ; 9. 68 (lH, s) ppm

N- (4-chloro-3-methylisothiazol-5-yl)- [2- (2, 2-dimethyl-3-hydroxypropyl) benzoxazol-5- yl] acetamide : 'H NMR (CDC13) 8 : 1. 05 (6H, s) ; 2. 38 (3H, s) ; 2. 82 (lH, t) ; 2. 95 (2H, s) ; 3. 45 (2H, s) ; 3. 98 (2H, s) ; 7. 28 (lH, dd) ; 7. 53 (lH, d) ; 7. 62 (lH, d) ; 8. 23 (lH, br) ppm EXAMPLE 3 This examples illustrates the preparation of Compound 23, N- (4-chloro-3- methylisothiazol-5-yl)- [2- (2, 2-dimethyl- 3-methoxyiminopropyl) benzoxazol-5- yl] acetamide A mixture of N- (4-chloro-3-methylisothiazol-5-yl)- [2- (2-formyl-2- methylpropyl) benzoxazol-5-yl] acetamide (0. 353 g, 0. 0008 mol), O-methylhydroxylamine hydrochloride (0. 084 g, 0. 001 mol) and pyridine (0. 074 g, 0. 001 mol) were stirred together in refluxing ethanol (5 ml) for 5 hours. The mixture was cooled to room temperature, the solvent evaporated in vacuo and the residue partitioned between ethyl acetate and water. The organic extracts were washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate : hexane 1 : 1 to give N- (4-chloro-3- methylisothiazol-5-yl)- [2- (2, 2-dimethyl-3-methoxyiminopropyl) benzoxazol-5-yl] acetamide (0. 234 g) as a yellow gum.

'H NMR (CDC13) 8 : 1. 25 (6H, s) ; 2. 38 (3H, s) ; 3. 08 (2H, s) ; 3. 79 (3H, s) ; 3. 98 (2H, s) ; 7. 29 (1H, dd) ; 7. 47 (lH, s) ; 7. 53 (lH, d) ; 7. 64 (lH, d) ; 8. 13 (lH, br) ppm EXAMPLE 4 This Example illustrates the preparation of Compound 26, N- (4-chloro-3- methylisothiazol-5-yl)-N-ethoxymethyl-{ [2-(bicyclo [2. 2. 1] heptan-2- yl) methyl] benzoxazol-5-yl} acetamide N, O-bis (trimethylsilyl) acetamide (0. 365 g, 0. 0018 mol) was added to a solution of, N-(4-chloro-3-methylisothiazol-5-yl)- { [2-(bicyclo [2. 2. 1] heptan-2-yl) methyl] benzoxazol-5- yl} acetamide (Compound 5, prepared by an analogous procedure to that used in Example 2, Step 1, 0. 623 g, 0. 0015 mol) in dichloromethane (5 ml), and the mixture was stirred at room temperature for 15 minutes. Chloromethyl ethyl ether (0. 284 g, 0. 003 mol) was added and the mixture was stirred at room temperature for 43 hours. The reaction mixture was poured into saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica gel to

give N- (4-chloro-3-methylisothiazol-5-yl)-N-ethoxymethyl- { [2- (bicyclo [2. 2. 1] heptan-2- yl) methyl] benzoxazol-5-yl} acetamide (0. 25 g), as a gum.

'H NMR (CDC13) 8 : 1. 2 (7H, m) ; 1. 5 (4H, m) ; 2. 09 (2H, m) ; 2. 25 (lH, br) ; 2. 5 (3H, s) ; 2. 7-2. 85 (2H, m) ; 3. 6 (2H, q) ; 3. 7 (2H, br) ; 5. 1 (2H, br) ; 7. 05 (lH, br) ; 7. 38 (2H, br) ppm EXAMPLE 5 This Example illustrates the pesticidal/insecticidal properties of compounds of formula (1). The activities of individual compounds of formula (I) were determined using a variety of pests. The pests were treated with a liquid composition containing 500 parts per million (ppm) by weight of a compound of formula (I). Each composition was made by dissolving the compound in an acetone and ethanol (50 : 50 by volume) mixture and diluting the solution with water containing 0. 05% by volume of a wetting agent, SYNPERONIC NP8, until the liquid composition contained the required concentration of the compound.

SYNPERONIC is a registered trade mark.

The test procedure adopted with regard to each pest was essentially the same and comprised supporting a number of the pests on a medium, which was usually a substrate, a host plant or a foodstuff on which the pests feed, and treating either or both the medium and the pests with a composition. Pest mortality was assessed usually between two and five days after treatment.

In each test against peach potato aphids (Myzus persicae), Chinese cabbage leaves were infested with aphids, the infested leaves were sprayed with a test composition and pest mortality was assessed after three days.

Similar tests were conducted against, independently, two-spotted spider mites (Tetranychus urticae), house flies (Musca domestica), fruit flies (Drosophila melanogaster), tobacco budworms (Heliothis virescens), diamond back moth (Plutella xylostella), pink bollworm (Spodoptera exigua) and corn root worm (Diabrotica balteata).

Tests were also conducted against root knot nematodes (Meloidogyne incognita) using an in vitro test in which nematodes were suspended in a liquid composition which had been prepared as described above except that it contained a concentration of 12. 5ppm by weight of a compound of formula (I) and it contained no SYNPERONIC NP8.

Results from these tests are displayed in Table 3, in which each mortality (score) is designated as 9, 5 or 0 wherein 9 indicates 80-100% mortality, 5 indicates 40-79% mortality and 0 indicates less than 40% mortality.

TABLE 3 Compound No Myzus Diabrotica Heliothis Plutella Tetranychus 1 9 5 4 9 0 0 0 5 9 5 9 5 5 9 5 9 5 6 9 0 0 0 9 0 0 9 0 11 0 0 9 0 13 0 0 5 0 14 0 0 5 0 11 0 0 9 0 13 0 0 5 0 14 0 0 5 0 17 0 0 9 0 18 0 0 5 0 19 0 0 5 0 21 0 0 5 0 22 0 9 9 5 23 9 5 9 9 24 9 0 0 5 25 0 9 5 9 26 9 5 0 5 32 5 5 5 9 33 0 5 0 0 34 0 5 0 5 35 0 5 5 0 36 9 9 0 9

EXAMPLE 6 This Example illustrates the fungicidal properties of compounds of formula (I). The compounds were tested against a variety of foliar fungal diseases of plants. The technique employed was as follows.

Plants were grown in John Innes Potting Compost (No. 1 or 2) in 4cm diameter, 3. 5cm depth minipots. The test compounds were individually formulated as a solution either in acetone or acetone/ethanol (1 : 1 by volume) which was diluted in deionised water to a

concentration of 100ppm (that is, lmg of compound in a final volume of lOml) immediately before use. When foliar sprays were applied to monocotyledonous crops, TWEEN 20 (0. 1% by volume) was added. TWEEN is a registered trade mark.

Individual compounds of formula (1) were applied as a foliar (Folr) application (where the chemical solution was applied to the foliage of the test plants by spraying the plant to maximum droplet retention.) These tests were carried out against Uncinula necator (UNCINE), on vines ; Phytophthora infestans lycopersici (PHYTIN) on tomatoes ; Puccinia recondita (PUCCRT), on wheat ; and Pyricularia oryzae (PYRIOR) on rice. Each treatment was applied to two or more replicate plants for Phytophthora infestans lycopersici and Uncinula necator. For tests on Puccinia recondita and Pyricularia oryzae two replicate pots each containing 6 to 10 plants were used for each treatment. The plants were inoculated one day before (Erad) or one day after (Prot) chemical application. The Phytophthora infestans lycopersici, Puccinia recondita and Pyricularia oryzae plants were inoculated with a calibrated fungal spore suspension. The Uncinula necator plants were inoculated using a'blowing'inoculation technique.

After chemical application and inoculation, the plants were incubated under high humidity conditions and then put into an appropriate environment to allow infection to proceed, until the disease was ready for assessment. The time period between chemical application and assessment varied from five to fourteen days according to the disease and environment. However, each individual disease was assessed after the same time period for all compounds.

Assessments were performed on each of two leaves on each of the replicate plants for Phytophthora infestans lycopersici. Assessments were performed on a single leaf of each of the replicate plants for Uncinula necator. For Puccinia recondita and Pyricularia recondita assessments were carried out collectively on the plants in each replicate pot.

The disease level present (that is, the percentage leaf area covered by actively sporulating disease) was assessed visually. For each treatment, the assessed values for all its replicates were meaned to provide mean disease values. Untreated control plants were assessed in the same manner. The data were then processed by the method, described hereinafter, to provide PRCO (Percentage Reduction from Control) values.

An example of a typical calculation is as follows : Mean disease level for treatment A = 25% Mean disease level on untreated controls = 85% PRCO = 100- {Mean disease level for treatment A} x 100 {Mean disease level on untreated controls} = 100- (25 x 100) = 70. 6 85 The PRCO is then rounded to the nearest whole number ; therefore, in this particular example, the PRCO result is 71.

It is possible for negative PRCO values to be obtained.

TABLE 4 COMPOUND UNCINE PYRIOR PUCCRT PHYTIN NO. Erad Prot Prot Prot 1 95 14 97 100 2 99 73 100 91 Key to Table 4:<BR> PHYTIN = Phytophthora infestans lycopersici<BR> PUCCRT = Puccinia recondita<BR> PYRIOR = Pyricularia oryzae<BR> UNCINE = Uncinula necator