ZA200406568B

ZA200406568B - 5-substituted-alkylaminopyrazole derivatives as pesticices

Info

Publication number: ZA200406568B
Application number: ZA200406568A
Authority: ZA
Inventors: David T Chou; Henricus M Bastiaans; Anke Kuhlmann; Maria-Theresia Thoenessen; Stefan Schnatterer; Uwe Doeller; Jamin Huang; Karl Seeger; Andrew Scribner; De Leon Adalberto A Pereze
Original assignee: Bayer Cropscience Sa
Priority date: 2002-03-05
Filing date: 2004-08-18
Publication date: 2006-05-31
Also published as: ZA200406569B

Description

Description 5-SUBSTITUTED-ALKYLAMINOPYRAZOLE DERIVATIVES AS PESTICIDES

The invention relates to the use for the control of pests (including insects arachnids and helminths (including nematodes)) of 5-substituted-alkylaminopyrazole derivatives, to novel compounds and compositions used therein, and to processes used for their preparation.

The control of insects, arachnids and helminths with 1-arylpyrazole compounds has been described in, for example, patent publication numbers WO 93/06089, WO 94/21606, WO 87/03781, EP 0295117, EP 659745, EP 679650, EP 201852 and

U.S. 5,232,940. The control of parasites in animals with 1-arylpyrazole compounds has also been described in, for example, patent publication numbers WO 00/35884,

EP 0846686, WO 98/24769 and WO 97/28126.

In addition, WO 02/066423 describes a process for preparing l-arylpyrazole compounds.

However, the level of action and/or duration of action of these prior-art compounds is not entirely satisfactory in all fields of application, in particular against certain organisms or when low concentrations are applied.

Since modem pesticides must meet a wide range of demands, for example regarding level, duration and spectrum of action, use spectrum, toxicity, combination with other active substances, combination with formulation auxiliaries or synthesis, and since the occurrence of resistances is possible, the development of such substances can never be regarded as concluded, and there is constantly a high demand for novel compounds which are advantageous over the known compounds, ) at least as far as some aspects are concemed.

It was an object of the present invention to provide compounds which widen the spectrum of the pesticides in various aspects, specifically with regard to the control of parasites in animals.

The present invention provides a method of controlling parasites in or on an animal comprising administering to the animal a parasiticidally effective amount of a 5- . substituted-alkylaminopyrazole derivative of formuia (1):

R8S(0); Rt re II

Soon NT

R ZW x

R3 (1) wherein:

R'is CN;

W is C-halogen or C-CH;

R? is hydrogen, halogen or CHa:

R? is (C4-Ca)-haloalky!, (C4-C3)-haloalkoxy or S(0)p-(C1-Ca)-haloalkyl;

R* is hydrogen, (C,-Cs)-alkenyl, (C,-Cg)-haloalkenyl, (C2-Ce)-alkynyl, (Co- :

Ce)-haloalkynyl, (C3-C7)-cycloalkyl, CO-(CH,)-R’, -COR’, CO-(CHp)q-R®, -CO-~(Cs-

Ca)-alkyl-(C1-Ce)-alkoxy, -CO,-(CHz)q-R’, CO2R®, -CO2(CH2)q-R®, -CO-(Cs-

Cy)-cycloalkyl, -CO2~(C1-Ca)-alkyl-(C3-Cr)-cycloalkyl, -CO,~(C3-Cg)-alkenyl, -CO2-(Cs-

Ce)-alkynyl, CONR"R", -CH,R’, -CH,R®, OR”, OR® or OR?; or (C1-Ce)-alky! unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C,-Cg)-alkoxy, (C1-C¢)-haloalkoxy, (C3-C;)-cycloalkyl,

S(O)R®, CO,~(C4-Ce)-alkyl, -O(C=0)-(C;-Ce)-alkyl, NR'°COR"2, NR'R",

CONR'"R", SO,NR'’R", OH, CN, NO,, OR’, NR'’SO,R?, COR® and OR’;

A is (C1-C12)-alkylene [preferably (C4-C¢)-alkylene] or (C1-C12)-haloalkylene ) [preferably (C1-Ce)-haloalkylene] in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Cg)-cycloalkyl ring which is unsubstituted or substituted by one qr more radicals selected from the group consisting of (C4-Cg)-alkyl and halogen; or is (C4-Cq2)-alkylene or (C1-C12)-haioalkylene in which last two mentioned groups a methylene moiety is replaced by a group selected from -C(=0)-, -C(=NH)-, -0O-, -§-

and -NR®-, with the proviso that the replacing group is not bonded to the adjacent O or N atom; or is (C-Ci2)-alkenylene or (C2-C12)-haloalkenylene;

Ris H, (C3-Ce)-alkenyl, (C3-Ceg)-haloalkenyl, (C3-Ce)-alkynyl, (C3-Cs)-haloalkynyit, . (C3-Cr)-cycloalkyl, «(CH,)qR’, ~(CH,)qR® or NR'°R'"; or is (C,-Cg)-alky! unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-Ce)-alkoxy, (C4-Cg)-haloalkoxy, (C3-Cg)-alkenyloxy, (C3-Cs)-haloalkenyloxy, (Ca-

Ce)-alkynyloxy, (C3-Cs)-haloalkynyloxy, (C3-Cr)-cycloalkyl, S(O),R®, CN, NO,, OH,

COR™, NR'COR'?, NR'°SO,R®?, CONR'R'’, NR'R"!, S(0),R’, S(O),R®, OR’, OR® and COR; or when A is (Cy-C12)-alkylene or (C-C12)-haloalkylene and R® is (Ci-

Ce)-alkyl unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R® may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;

R® is (C4-Cg)-alkyl, (C+-Ce)-haloalkyl, (C2-Ce)-alkenyl, (C,-Ce)-haloalkenyl, (Co-

Cs)-alkynyl or (C,-Cg)-haloalkynyl;

R” is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cg)-alkyl, (C+-Cs)-haloalkyl, (C4-Cg)-alkoxy, (C4-Ce)- haloalkoxy, CN, NO, S(0O),R®, COR", COR'3, CONR'R"!, SO,NR'R'!, NR'R"",

OH, SO3H and (C4-Cg)-alkylideneimino;

R® is (C4-Cg)-alkyl or (C4-Cg)-haloalkyl;

R® is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cs)-alkyl, (C4-Cs)-haloalky!, (C4-Cs)-alkoxy, (C+-

Cs)-haloalkoxy, NO», CN, CO,(C4-Cs)-alkyl, S(O),R® OH and oxo;

R'® and R'? are each independently H, (C;-Ce)-alkyl, (C1-Ce)-haloalkyl, (C3-Ce)- alkenyl, (Cs-Ce)-haloalkenyl, (C3-Ce)-alkynyl, (C3-Ce)-haloalkynyl, (Cs-Ce)-cycloalkyi,

C+-Ce)-alkyl{C3-Cg)-cycloalkyl, CH2)R"? or ~(CH2)qR%; or - R¥ and R" and/or R' and R'? each together with the respective attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cg)-alkyl and (C4-Cg)-haloalkyl;

R'' and R" are each independently H, (C1-Ce)-alkyl, (C1-Ce)-haloalkyl, (C3-Cs)-cycloalkyl or (C1-Ce)-alkyl-(C3-Ce)-cycloalkyt; y

R™is phenyl unsubstituted or substituted by one or more radicals selected from the ] . group consisting of halogen, (C,-Cs)-alkyl, (C+-Ce)-haloalkyl, (C,-Ce)-alkoxy, (C1-Cs)- haloalkoxy, CN, NO, S(O),R® and NR''R™; } R¥is R" or (CH,)R">; n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S; or a pesticidally acceptable salt thereof.

In a further aspect of the invention there is provided the use of compounds of formula (I) for the control of parasites in and on animals.

In yet a further aspect of the invention there is provided the use of compounds of formula (1) for preparing a veterinary medicament, preferably for the treatment of parasites, specifically ecto and endo parasites, in and on animals.

The invention also encompasses any stereoisomer, enantiomer or geometric isomer, and mixtures of the compounds of the formula (1).

By the term "pesticidally acceptable salts" is meant salts the anions or cations of which are known and accepted in the art for the formation of salts for pesticidal use.

Suitable salts with bases, e.g. formed by compounds of formula (I) containing a carboxylic acid group, include alkali metal (e.g. sodium and potassium), alkaline earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts. Suitable acid addition salts, e.g. formed by compounds of formula (1) ) containing an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.

It is to be understood that the above mentioned provisos are included only for ) reasons of chemical instability for the particular excluded moieties, and not for reasons of prior art. oo :

In the present patent specification, including the accompanying claims, the aforementioned substituents have the following meanings:

Halogen atom means fluorine, chlorine, bromine or iodine.

The term "halo" before the name of a radical means that this radical is partially or completely halogenated, that is to say, substituted by F, CI, Br, or |, in any combination, preferably by F or Cl.

Alkyl groups and portions thereof (unless otherwise defined) may be straight- or branched-chain.

The expression “(C-Ce)-alky!” is to be understood as meaning an unbranched or branched hydrocarbon radical having 1, 2, 3, 4, 5 or 6 carbon atoms, such as, for example a methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropy! or tert- butyl radical.

Alkyl radicals and also in composite groups, unless otherwise defined, preferably have 1 to 4 carbon atoms. "(C4-Ce)Haloalkyl" means an alkyl group mentioned under the expression "(C+-Ce)alkyl" in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, such as monohaloalkyl, perhaloalkyl,

CF3;, CHF, CHF, CHFCHj;, CF3CH,, CF3CF,, CHF 2CF,, CH,FCHCI, CH,CI, CCl,

CHCIz or CH>CH,CI.

The expression “(C4-C42)-alkylene” is to be understood as meaning an unbranched or branched saturated carbon chain having from 1 to 12 carbon atoms.

The expression “(C4-C2)-haloalkylene” is to be understood as meaning an unbranched or branched saturated carbon chain having from 1 to 12 carbon atoms, ) in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, }

The expression “(C2-C42)-alkenylene” is to be understood as meaning an unbranched or branched saturated carbon chain having from 2 to 12 carbon atoms,

: | 6 and which contains at least one double bond which can be located in any position of the respective unsaturated radical. ) "(C1-Ce)Alkoxy" means an alkoxy group whose carbon chain has the meaning given : under the expression "(C4-Cg)alkyl”. “Haloalkoxy” is, for example, OCF;, OCHF,

OCH_F, CF3;CF,0, OCH,CF3 or OCH,CH,CI. "(C2-Ce)Alkenyl" means an unbranched or branched non-cyclic carbon chain having a number of carbon atoms which corresponds to this stated range and which contains at least one double bond which can be located in any position of the respective unsaturated radical. "(C,-Cg)Alkenyl" accordingly denotes, for example, the vinyl, allyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or the hexenyl group. : Co "(C2-Ce)Alkynyl” means an unbranched or branched non-cyclic carbon chain having a number of carbon atoms which corresponds to this stated range and which contains one triple bond which can be located in any position of the respective unsaturated radical. "(C2-Cs)Alkynyl" accordingly denotes, for example, the propargyl, 1-methyl-2-propynyl, 2-butyny! or 3-butynyi group.

Cycloalkyl groups preferably have from three to seven carbon atoms in the ring and are optionally substituted by halogen or alkyl.

In compounds of formula (1) the following examples of radicals are provided:

An example of alkyl substituted by cycloalkyl is cyclopropyimethyt; an example of alkyl substituted by alkoxy is methoxymethyl (CH3OCH,-); and an example of alkyl substituted by alkylthio is methyithiomethyl (CH3SCH,-).

A “heterocyclyl” group can be saturated, unsaturated or heteroaromatic; it preferably contains one or more, in particular 1, 2 or 3, hetero atoms in the heterocyclic ring, preferably selected from the group consisting of N, O and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 to 7 ring atoms. The heterocyclic radical can be, for example, a ’ heteroaromatic radical or ring (heteroaryl) such as, for example, a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more hetero ~~ atoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, : thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl, or it is a partially or fully hydrogenated radical such as oxiranyl, oxetanyi,

“ | 7 oxolany! (= tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. The “heterocyclyl” group may be unsubstituted or substituted by one or more radicals : (preferably 1, 2 or 3 radicals) selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, alkoxycarbonyl, alkylcarbonyi, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, ~ alkylsulfonyl, haloalkylsulfony!, alkyl and haloalkyl, and additionally also oxo. The oxo group can also be present at those hetero ring atoms where various oxidation numbers are possible, for example in the case of N and S.

The term pests means arthropod pests (including insects and arachnids), and helminths (including nematodes). The term parasites embraces all kinds of pests that live in or on animals.

A preferred class of compounds of formula (I) for use in the invention are those in which:

R'is CN;

W is C-halogen;

R? is hydrogen or halogen;

R®is CF; or OCF3;

R* is hydrogen, (C,-Cs)-alkenyl, (C;-Cs)-haloalkenyl, (C,-Cs)-alkynyl, (Co-

Ce)-haloalkynyl, (Cs-C7)-cycloalkyl, -CO2R8, -CH2R’, -CH,R®, OR’, OR® or OR®; or (C4-Cs)-alky! unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C,-Cg)-alkoxy, (C+-Cs)-haloalkoxy, (Cs-C7)-cycloalkyl,

S(0),R® and CO,-(C4-Cs)-alkyl;

A is (C4-Ceg)-alkylene or (C1-Cg)-haloalkylene, in which 2, 3 or 4 adjacent carbon ’ atoms optionally form part of a (C3-Ce)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (Cq-

Ce)-alkyl and halogen; :

RS is (Ca-Ce)-cycloalkyl, {CH,)qR’; or (C4-Cg)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C,-Cg)-alkoxy, oo El

(C4-Csg)-haloalkoxy, (C3-Cg)-cycloalkyl, S(O),R® and CO2-(C4-Ce)-alkyl; or when A is } (C4-Ce)-alky! or (C4-Cg)-haloalkyl and R® is (C+1-Ce)-alkyl or (C1-Ce)-haloalkyl, one or more of the carbon atoms of the R® group may, together with O and one or more of . the carbon atoms of A, form a 5- or 6-membered ring;

R® and R® are each independently (C+-Cg)-alkyl or (C+-Cg)-haloalkyl;

R’ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-Cg)-alkyl, (C4-Cg)-haloalkyl, (C1-Cg)-alkoxy, CN,

NO,, S(0),R? and NR''R"%;

Ris heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cas)-alkyl, (C1-Cs)-haloalkyl and (C,-Cs)-alkoxy;

R' and R'? are each the same or different hydrogen, (C1-Cs)-alky! or (C4-

Cs)-haloalkyl; n and p are each independently zero, one or two; and q is zero or one.

Another preferred class of compounds of formula (1) for use in the invention are those in which:

R'is CN;

W is C-halogen,;

R? is halogen;

R® is CF; or OCF3;

R* is hydrogen, (C2-Cg)-alkenyl, (C,-Ce)-alkynyl, (C3-C7)-cycloalkyl, -CO(Cr-

Ca)-alkyl, -CO2-(C3-Cs)-cycloalkyi, -CO2~(C1-Ca)-alkyl-(C3-Cg)-cycloalkyl, -CH,R’ or -CH2R?; or (C4-C4)-alky! unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-C;)-alkoxy, (C1-Cs)-haloalkoxy, (C3-Ce)-cycloalkyl, S(O),R®, CO2-(C1-Cs)-alkyl, -O(C=0)-(C+-Cs)-alkyl, NR'°R"", OH,

CN, NO, OR’ or OR,

A is (C4-Cg)-alkylene or (C;-Cq)-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (Ca-Cs)-cycloalky! ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C4-

Ce)-alkyl and halogen;

R® is (C3-Cr)-cycloalkyl or (CH,),R’; or is (C1-Ce)-alkyl unsubstituted or substituted ] by one or more radicals selected from the group consisting of halogen, (C4-C3)- alkoxy, (C1-Ca)-haloalkoxy, (C3-Cy)-cycloalkyl, S(O),R®, CN, NR'°R"!, S(O),R’, : S(0),R®, OR” and OR®;

R® is (C4-C,)-haloalky!;

R” is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-C4)-alkyl, (C4-C4)-haloalkyl, (C4-C,4)-alkoxy, (C1-Ca4)- haloalkoxy, CN, NO, S(0O),R®, COR, NR'R"" and OH;

R® is (C4-C4)-alkyl or (C1-C4)-haloalkyl;

R® is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cs)-alkyl, (C1-C4)-haloalkyl and (C4-C4)-alkoxy;

R'is H, (C4-C3)-alkyl, (C+-Cs)-haloalkyl, (C3-Cs)-alkenyl, (C3-Cy4)-alkynyl, (C3-Ce)-cycloalkyl!, -(C4-Cg)-alkyl-(C3-Cg)-cycloalky! or —(CH2)R™; or

R' and R"! together with the attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C4-Cj3)-alkyl;

R' and R' are each independently H, (C4-Cs)-alkyl, (C1-C3)-haloalkyl, (Cs-Cs)-cycloalkyl or -(C4-C3)-alkyl~(Cs-Ce)-cycloalkyl;

R'is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cs)-alkyl, (C1-C3)-haloalkyl, (C4-C3)-alkoxy, (C1-C3)- haloalkoxy, CN, NO2, S(O),R® and NR''R™: n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl in the above-mentioned radicals is independently a heteroaromatic radical having 5 or 6 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.

A further preferred class of compounds of formula (I) for use in the invention are those in which: .

R'is CN;

Wis C-Cl;

R?is chlorine;

Ris CFyor OCF; oo

R*is hydrogen, CO,(C4-Cs)-alkyl, or (C+-Ce)-alkyl unsubstituted or substituted by : one or more radicals selected from the group consisting of halogen and (C4-

Cj)-alkoxy;

Ais (C4-Cy)-alkylene; - R%is (C3-Cs)-cycloalkyl, {CHa)qR’, (C1-Ce)-alkyl or (C4-Cg)-haloalkyl; or when RS is (C4-Ce)-alkyl, one or more of the carbon atoms of the R® group may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;

R® is CF3, CF4Cl, CFCly, CBrF or CHF;

R’ is phenyl; n is zero, one or two; and q is zero or one.

Another preferred class of compounds of formula (I) for use in the invention are those in which:

R'is CN;

W is C-halogen;

R? is hydrogen or halogen;

R®is CF; or OCF3;

R* is hydrogen, (C2-Cg)-alkenyl, (C»-Ce)-haloalkenyl, (C2-Ce)-alkynyl, (C,-

Ce)-haloalkynyl, (C3-Cs)-cycloalkyl, -CO2-(C4-Cs)-alkyl or -CHR; or (C4-Cg)-alky! unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-Ce)-alkoxy, (C1-Ce)-haloalkoxy, (C3-Ce)-cycloalkyl, S(O),R® and CO2-(C+-Ce)-alkyl;

A is (C4-Ce)-alkylene or (C4-Cg)-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Ce)-cycloalkyl ring which is unsubstituted or ’ substituted by one or more radicals selected from the group consisting of (C;-

Cs)-alkyl and halogen;

RS is (C3-Cs)-cycloalkyl or ~CH)RT; or is (C4-Ceg)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Ce)- alkoxy, (C+-Cs)-haloalkoxy, (C3-Ce)-cycloalkyl, S(0O),R® and CO,-(C4-Cg)-alkyl; or a | 11 when A is (C4-Cg)-alkylene or (C,-Ce)-haloalkylene and R® is (C4-Ce)-alkyl ] unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R® may, together with O and one or more of the carbon atoms of A, : form a 5- or 6-membered ring;

R® and R® are each independently (C1-Cs)-alkyl or (C1-Cg)-haloalkyl;

R’ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkyl, (C1-Cg)-haloalkyl, (C4-Cg)-alkoxy, CN,

NO, S(0),R® and NR'R";

Rand R'" are each independently H, (C4-Cg)-alkyl or (C1-Cg)-haloalky!: n and p are each independently zero, one or two; and q is zero or one.

A further preferred class of compounds of formula (I) for use in the invention are those in which:

R'is CN; © Wis C-haiogen;

RZ? is halogen;

R®is CF; or OCF3;

R* is hydrogen, (C,-Cg)-alkenyl, (C,-Cg)-haloalkenyl, (C3-C)-cycloalky!, (C+-

C4)-alkyl-(C3-C7)-cycloalkyji, -CO,-(C1-Ce)-alkyl, (C4-Ce)-alkyl or (C4-Cg)-haloalkyl;

A is (C4-Cqz)-alkylene which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C4-Cg)-alkyl and halogen;

RS is (C4-Ce)-alkyl;

R® is CF3, CF,Cl, CFCl,, CBrF; or CHF; and n is zero, one or two.

Further especially preferred classes of compounds of formula (I) for use in the invention are those in which one or more of the following features are present:

R? is hydrogen, (C1-C4)-alkyl, -CO2-(C+-Ca)-alkyl, (C3-Ca)-alkenyl, (C4-C2)-alkyl-(Cs-

C4)-cycloalkyl or (C3-Ca)-cycloalkyl;

R® is (C1-C,)-alkyl; and

A is (C-C3)-alkylene. : Another especially preferred class of compounds for use in the invention are those wherein:

R'is CN;

R? is chlorine;

R%is CF3;

Wis C-Cl;

R* is hydrogen, (C+-Ca)-alkyl, -CO2~(C1-Cy4)-alkyl, (C3-C4)-alkenyl, (C4-C;)-alkyl-(Cs-

C4)-cycloalkyl, or (C3-Cs)-cycloalkyl,

R® is (C4-Cy)-alkyl;

R® is CF3;

A is (C,-Cs)-alkylene; and nis zero, one or two.

Another especially preferred class of compounds for use in the invention are those wherein:

R'is CN;

R2 is chlorine;

R%is CF3;

Wis C-CI;

R* is hydrogen, (C4-Ca)-alky! or -CHa-(C+-Cq)-alkoxy;

R’ is hydrogen, (C4-C4)-alkyl or CO2-(C1-Cs)-alkyl;

Ris CF3;

A is (C2-Cs)-alkylene; and n is zero, one or two.

A more preferred class of compounds of formula (I) for use in the invention are those in which:

R'is CN; R? is chlorine; R? is CF; or OCF3; W is C-Cl; R* is hydrogen or (C1-Ce)- alkyl; RS is (C4-Ce)-alkyl; R® is CFs: Ais (C1-Ca)-alkylene and n is zero, one or two.

Further especially preferred classes of compounds of formula (1) for use in the invention are those wherein one or more of the following features are present: - . Wis C-Cl;

R? is chlorine;

R3 is CF; or OCF3;

R* is hydrogen, (C4-Cs)-alkyl or (C4-Ce)-haloalky!:

RS is (C1-Cs)-alkyl;

R® is (C4-Ca)-haloalkyl (R® is more preferably CFs); and/or

A is (C4-Ce)-alkylene (more preferably A is (C2-Cs)-alkylene).

WO 9828278 discloses a number of compounds which fall within the above formula (1) as intermediates, however there is no reference or suggestion that these compounds possess parasiticidal properties.

Some of the compounds of formula (I) are new and a further feature of the present invention is therefore directed to the novel compounds of formula (1).

One class of novel 5-substituted-alkylaminopyrazole derivatives of formula (n, or pesticidally acceptable salts thereof, are those wherein:

R'is CN;

W is C-halogen or C-CHj;

R? is hydrogen, halogen or CH; :

R? is (C1-Ca)-haloalkyl, (C4-C3)-haloalkoxy or S(0)p-(C1-C3)-haloalkyl;

R* is (C2-Ce)-alkenyl, (C2-Cg)-haloalkenyi, (C2-Ce)-alkynyl, (C,-Ce)-haloalkynyl, (Cs

Cr)-cycloalkyl, CO-~(CH,)q-R’, CO-~(CHy)q-R?, ~-CO-(C;-Ca)-alkyl-(C4-Cg)-alkoxy, -COx(CHz)q"R’, -CO2R®, -CO.-(CHa)4-R®, -COHC3-C7)-cycioalkyl, -CO(Cs-

Cs)-alkyl-(C3-Cy)-cycloalkyl, -CO,(C3-Cg)-alkenyl, -CO,-(Ca-Ce)-alkynyl, CONR"R, -CHR’, -CH,R®, OR’, OR® or OR®; or (C1-Ce)-alkyl which is substituted by one or more radicals selected from the group consisting of halogen, (C1-Ce)-alkoxy, (Cs-

Ce)-haloalkoxy, (C3-Cr)-cycloalkyl, S(O),R®, CO2(C1-Ce)-alkyl,

. “O(C=0)-(C+-Ce)-alkyl, NR'®COR'?, NR"R"!, CONR™R", SO,NR™R"!, OH, CN,

NO., OR’, NR'’SO,R8, COR? and OR®;

Ais (C4-Cy2)-alkylene [preferably (C4-Cs)-alkylene] and (C4-Cy,)-haloalkylene } [preferably (C,-Cs)-haloalkylene] in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Cs)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-Cg)-alkyl and halogen; or is (C+-Caz)-alkylene or (C4-C42)-haloalkylene in which last two mentioned groups a methylene moiety is replaced by a group selected from -C(=0)-, -C(=NH)-, -O-, -S-. and -NR™-, with the proviso that the replacing group is not bonded to the adjacent O or N atom; or is (C2>-C12)-alkenylene or (C,-Ciz)-haloalkenylene;

R® is H, (C3-Cs)-alkenyl, (C3-Ce)-haloalkeny!, (C3-Csg)-alkynyl, (C3-Cg)-haloatkynyl, (C3-Cr)-cycloalkyl, {(CH2)qR’, =(CH2)4R® or NR'°R""; or is (C-Ce)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-Ce)-alkoxy, (C+-Ce)-haloalkoxy, (Cs-Cs)-alkenyloxy, (Cs-Cs)-haloalkenyloxy, (Cs-

Ce)-alkynyloxy, (C3-Ce)-haloalkynyloxy, (C3-C7)-cycloalkyl, S(O)R®, CN, NO, OH,

COR", NR'°COR'?, NR'°SO,R8, CONR'R!!, NR'R"!, S(0),R’, S(O),R’, OR", OR® and COzR"; or when A is (C1-C1,)-alkylene or (C1-Ci2)-haloalkylene and R° is (Cs-

RS is (C4-Cs)-alkyl, (C4-Ce)-haloalkyl, (C2-Cg)-alkenyl, (C.-Cg)-haloalkenyl, (Co-

Cs)-alkynyl or (C>-Ceg)-haloalkynyl;

R” is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkyl, (C1-Cg)-haloalkyl, (C4-Cg)-alkoxy, (C1-Ce)- haloalkoxy, CN, NO2, S(O),R®, COR", COR", CONR'"R"!, SO,NR'"R"', NR'R"",

OH, SO3zH and (C4-Cg)-alkylideneimino;

R8 is (C;-Cs)-alkyl or (C4-Cg)-haloalkyl; :

R® is heterocyclyi unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cs)-alkyl, (C1-Ca)-haloalkyl, (C4-Ca)-alkoxy, (Cs-

Ca)-haloalkoxy, NOz, CN, COy(C1-Ce)-alkyl, S(O)R®, OH and oxo:

R™ and R' are each independently H, (C1-Cé)-alkyl, (C1-Cs)-haloalkyl, (Cs-Ce)- alkenyl, (C3-Cs)-haloalkenyl, (C3-Cs)-alkyny!, (C3-Cs)-haloalkynyl, (C3-Ce)-cycloalkyl, -(C+-Cé)-alkyl-(C5-Cg)-cycloalkyl, ~(CHz)qR"® or ~(CH,)R®; or

R™ and R'" and/or R™® and R*2 each together with the respective attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group © consisting of halogen, (C1-Cg)-alkyl and (C1-Cs)-haloalkyl;

R'' and R™ are each independently H, (C1-Ce)-alkyl, (C1-Cs)-haloalkyl, (C3-Cs)-cycloalkyl or -(C4-Cs)-alkyl-(C3-Cg)-cycloalkyl;

R"is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkyl, (C1-Cg)-haloalkyl, (C1-Cs)-alkoxy, (C1-Cé)- haloalkoxy, CN, NO2, S(O),R® and NR"'R™;

R'is R' or -(CH2)R™; n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.

A preferred class of compounds of formula (I) are those in which:

R'is CN;

W is C-halogen;

R? is hydrogen or halogen;

R® is CF3 or OCFy;

R? is (Co-Cs)-alkenyl, (C,-Cs)-haloalkenyl, (Co-Cg)-alkynyl, (C2-Cs)-haloalkynyl, (Ca-

Cr)-cycloalkyl, CO2,R®, -CO,-(C3-Cs)-alkenyl, -CO,(C3-Cs)-alkynyl, -CH2R’, -CHoR®,

OR’, OR® or OR?; or (C+-C)-alkyl which is substituted by one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkoxy, (C4-Cs)-haloalkoxy, (Cs-Cr)-cycloalkyl, S(O),R® and CO,-(C+-Ce)-alkyl;

A is (C1-Ce)-alkylene or (C4-Cg)-haloalkylene, in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-C¢)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C;-

Ce)-alkyl and halogen;

Ris (C3-Cs)-cycloalkyl, {CHz)qR; or (C1-Ce)-alkyl unsubstituted or substituted by : one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkoxy, (C4-Ce)-haloalkoxy, (C3-Cs)-cycloalkyl, S(0),R® and CO,-(C,-Cg)-alkyl; or when A is (C4-Ce)-alky! or (C4-Cs)-haloalkyl and R® is (C+-Cs)-alkyl or (C1-Ce)-haloalkyl, one or more of the carbon atoms of the R® group may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;

R® and R® are each independently (C;-Ce)-alky! or (C1-Cg)-haloalky!;

R'is phenyl! unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cs)-alkyl, (C4-Ce)-haloalkyl, (C1-Ce)-alkoxy, CN,

NO., S(O),R® and NR''R'?;

R? is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cs)-alkyl, (C4-C4)-haloalkyl and (C4-C4)-alkoxy;

R'" and R'? are each the same or different hydrogen, (C;-Cg)-alkyl or (C:-

Ce)-haloalkyl; n and p are each independently zero, one or two; and q is zero or one.

Another preferred class of compounds of formula (I) are those in which:

R'is CN; :

W is C-halogen;

R? is hydrogen or halogen;

Ris CF3 or OCF3;

R* is (Co-Ce)-alkenyl, (C,-Cg)-haloalkenyl, (C2-Cg)-alkynyl, (C,-Ce)-haloalkynyl, (Cs

Ce)-cycloalkyl, -CO,R®, -CO»-(Ca-Cs)-alkynyl, or -CH.R’; or (C4-Ce)-alkyl which is substituted by one or more radicals selected from the group consisting of halogen, ’ (C4-Ce)-alkoxy, (C1-Cs)-haloalkoxy, (C3-Ce)-cycloalkyl, S(0),R® and CO-(C:-

Ce )-alkyl; :

A is (C4-Ce)-alkylene or (C4-Cg)-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Ce)-cycloalky! ring which is unsubstituted or

A 17 substituted by one or more radicals selected from the group consisting of (C4-

Ce)-alkyl and halogen:

R® is (Cs-Cs)-cycloalkyl or (CH,)qR”: or is (C1-Ce)-alkyl unsubstituted or substituted : by one or more radicals selected from the group consisting of halogen, (C4-Cs)- alkoxy, (C4-Ce)-haloalkoxy, (C3-Cg)-cycloalkyl, S(0),R® and CO,-(C1-Cs)-alkyl; or ~ whenAis (C4-Ce)-alkylene or (C1-Ce)-haloalkylene and R® is (C1-Cg)-alkyl unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R® may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;

R°® and R® are each independently (C-Cg)-alkyl or (C1-Cs)-haloalkyl;

R’ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting. of halogen, (C1-Ceg)-alkyl, (C4-Cg)-haloalkyl, (C4-Cg)-alkoxy, CN,

NO,, S(O),R® and NR'°R™";

R' and R" are each independently H, (C;-Cs)-alkyl or (C4-Cs)-haloalky: n and p are each independently zero, one or two; and q is zero or one.

Another preferred class of compounds of formula (1) are those in which:

R'is CN;

Wis C-halogen;

R? is halogen;

R3is CF; or OCF3;

R* is (C2-Cg)-alkenyl, (C2-Ce)-alkynyl, (C3-C7)-cycloalky!, -CO,R®, -CO-(C3-

C6)-alkynyl, -CO2-(C3-Ce)-cycloalkyl, -CO»-(C4-C3)-alkyl-(C2-Cg)-cycloalkyl, -CH,R’ or

CHR’: or (C4-Cs4)-alkyl which is substituted by one or more radicals selected from the group consisting of halogen, (C4-C3)-alkoxy, (C4-C3)-haloalkoxy, (C3-Ce)- cycloalkyl, S(O),R®?, CO.-(C4-Cs)-alky!, -O(C=0)-(C,-C3)-alkyl, NR'R"!, OH, CN,

NO, OR’ and OR?

A is (C4-Cg)-alkylene or (C,-Cg)-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Cg)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C1-

Cs)-alkyl and halogen;

R® is (Ca-Cr)-cycloalkyl or {(CH,)qR’; or is (C1-Cs)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-C3)- alkoxy, (C+-Cy)-haloalkoxy, (C3-C;)-cycloalkyl, S(O),R®, CN, NR'R"", S(O),R’,

S(O)R®, OR” and OR%;,

RS is (C4-C2)-haloalkyl:

R’ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C,4)-alkyl, (C1-C4)-haloalkyl, (C4-Ca)-alkoxy, (C1-Ca)- haloalkoxy, CN, NO2, S(O),R®, COR", NR'R"! and OH;

R® is (C4-Ca)-alkyl or (C1-C4)-haloalkyl;

RY is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Ca)-alkyl, (C1-Cs)-haloalkyl and (C4-Cs)-alkoxy;

R'% is H, (C4-C3)-alkyl, (C1-Ca)-haloalkyl, (Ca-Cy)-alkenyl, (C3s-Cy4)-alkynyl, (C3-Ce)-cycloalkyt, -(C1-Ce)-alkyl-(C3-Cg)-cycloalkyl or (CH2)qR™; or

R'® and R'' together with the attached N atom form a five- or six-membered "saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C,4-C3)-alkyl;

R'" and R™ are each independently H, (C1-Cs)-alkyl, (C4-C3)-haloalkyl, (Ca-Cé)-cycloalkyl or -(C4-C3)-alkyl-(C3-Cg)-cycloalkyl;

R'3is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C4-C3)-alkoxy, (C+-C3)- haloalkoxy, CN, NO2, S(O),R® and NR''R"; n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl! in the above-mentioned radicals is independently a heteroaromatic radical having 5 or 6 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.

A further preferred class of compounds of formula (1) are those in which:

R'is CN;

W is C-CI;

R? is chlorine;

R® is CF3 or OCF3;

R* is CO2-(C1-C3)-alkyl, or (C4-Ce)-alkyl which is substituted by one or more radicals selected from the group consisting of halogen and (C-Cs)-alkoxy;

A is (C4-C4)-alkylene;

R® is (C3-Cs)-cycloalkyl, —(CH;)qR’, (C1-C)-alkyl or (C1-Ce)-haloalkyl; or when R® is (C+-Ce)-alkyl, one or more of the carbon atoms of the R® group may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;

R® is CFs, CF,Cl, CFCly, CBF, or CHF;

R is phenyl; n is zero, one or two; and q is zero or one.

A further preferred class of compounds of formula (1) are those in which:

R'is CN;

W is C-halogen; + R2is halogen;

R® is CF3 or OCF; ~ R*is (C2-Ce)-alkenyl, (C,-Cg)-haloalkenyl, (C3-C7)-cycloalkyl, (C4-Cs)-alkyl-(Ca-

C7)-cycloalkyl, -CO2-(C4-Cg)-alky! or (C4-Cg)-haloalkyl;

A is (C4-C42)-alkylene which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C4-Cs)-alkyl and halogen;

RS is (C4-Cg)-alkyl; -

R® is CF3, CF.Cl, CFCly, CBrF; or CHF»; and n is zero, one or two.

An especially preferred class of compounds of formula (1) are those wherein:

Ris CN:

R%is -CO2-(C1-Ca)-alkyl, (C3-C,)-alkenyl, (C4-Cz)-alkyl-(C3-Cs)-cycloalkyl or (C3-C,)- cycloalkyl (more preferably R* is -CO,-(C1-Cs)-alkyl);

R’ is (C4-C,)-alkyl:

RC is CFs; oo

Ais (C2-C;)-alkylene; and . n is zero, one or two.

Another class of novel 5-substituted-alkylaminopyrazole derivatives of formula (1), or a pesticidally acceptable salt thereof, are those wherein:

R'is CN;

W is C-halogen or C-CHs;

R? is hydrogen, halogen or CH;

Ris (C4-Cs)-haloalkyl, (C4-Cs)-haloalkoxy or S(O),-(C4-C3)-haloalky!;

R* is hydrogen, (C1-Cg)-alky! or COR®:

A is (C+-C+2)-alkylene [preferably (C4-Ce)-alkylene] and (C4-Cy2)-haloalkylene [preferably (C4-Cs)-haloalkylene] in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Cg)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C4-Cg)-alkyl and halogen; or is (C4-C42)-alkylene or (C4-C42)-haloalkylene in which last two mentioned groups a methylene moiety is replaced by a group selected from -C(=0)-, -C(=NH)-, -O-, -S- and -NR"-, with the proviso that the replacing group is not bonded to the adjacent O or N atom; or is (C2-C42)-alkenylene or (C,-Cy,)-haloalkenylene;

R® is H, (C3-Ce)-alkenyl, (C3-Cg)-haloalkenyl, (Ca-Ce)-alkynyl, (C3-Ce)-haloalkynyl, (C3-Cr)-cycloalkyl, {CH2)iR’, HCH2)qR® or NR'°R"™; or is (C1-Ce)-alkyl substituted by one or more radicals selected from the group consisting of halogen, (C4-Cs)- alkoxy, (C1-Ce)-haloalkoxy, (Cs-Cs)-alkenyloxy, (C3-Cs)-haloalkenyloxy, (C3-Ce)- alkynyloxy, (C3-Ce)-haloalkynyloxy, (Ca-C;)-cycloalkyl, S(O)R®, CN, NO,, OH,

COR, NR'°COR", NR'’SO,R®, CONR'R"!, NR'’R!, S(0),R, S(O),R?, OR’, OR® and CO-R"; or when A is (C4-Ci)-alkylene or (C1-C2)-haloalkylene and R® is (C:- - Cg)-alkyl unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R® may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;

R® is (C4-Ce)-haloalkyl;

21 oo

R’ is phenyl unsubstituted or substituted by one or more radicals selected from the * group consisting of halogen, (C;-Cg)-alkyl, (C4-Ce)-haloalkyl, (C1-Ce)-alkoxy, (C4-Ce)- haloalkoxy, CN, NO,, S(0),R®, COR", COR", CONR'R"! SO,NR'’R"!, NR"°R"", . OH, SO3H and (C4-Ce)-alkylideneimino;

R® is (C1-Cg)-alkyl or (C4-Cg)-haloalkyl;

RY is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cs)-alkyl, (C4-C4)-haloalkyl, (C1-Cs)-aikoxy, (Cs-

Ca)-haloalkoxy, NO, CN, CO»(C+-Ce)-alkyl, S(O),R®, OH and oxo;

R'® and R' are each independently H, (C1-Cg)-alkyl, (C1-Cg)-haloalkyl, (C3-Ce)- alkenyl, (Cs-Ce)-haloalkenyl, (Cs-Ce)-alkynyl, (C3-Cs)-haloalkynyl, (C3-Ce)-cycloalkyl, -(C1-Ce)-alkyl-(C3-Ce)-cycloalkyl, | CH2)qR"® or {CH2)qR®; or

R'™ and R"" and/or R" and R'? each together with the respective attached N atom . form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-Ce)-alkyl and (C,-Cg)-haloalkyl;

R' and R" are each independently H, (C,-Ce)-alkyl, (C1-Cs)-haloalkyl, (C3-Ceg)-cycloalkyl or -(C4-Cg)-alkyl-(C3-Cg)-cycloalkyl;

Ris pheny! unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-Cg)-alkyl, (C1-Cg)-haloalkyl, (C1-Cg)-alkoxy, (C1-Cs)- haloalkoxy, CN, NO,, S(O),R® and NR''R"4;

R'is R" or (CHz)R"™; n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.

A preferred class of compounds of formula (1) are those in which:

R'is CN;

Wis C-halogen;

R? is hydrogen or halogen;

Co | 22

R®is CF3 or OCF; oe

R* is hydrogen, (C4-Cs)-alkyl or COR®;

A is (C4-Ce)-alkylene or (C4-Cg)-haloalkylene, in which 2, 3 or 4 adjacent carbon : atoms optionally form part of a (C3-Cg)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C;-

Ce)-alkyl and halogen;

R® is (C3-Ce)-cycloalkyl, {(CH,),R’; or (C;-Ce)-alky! substituted by one or more radicals selected from the group consisting of halogen, (C-Cs)-alkoxy, (C1-Cg)- haloalkoxy, (C3-Ce)-cycloalkyl, S(O),R® and CO.-(C4-Cs)-alkyl; or when A is (C1-Ce)- alkyl or (C4-Ce)-haloalkyl and R® is (C4-Cg)-haloalkyl, one or more of the carbon atoms of the R® group may, together with O and one or more of the carbon atoms of

A, form a 5- or 6-membered ring; | :

R® is (C4-Cg)haloalkyl;

R® is (C1-Ce)-alkyl or (C4-Cg)-haloalkyl;

R’ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkyl, (C4-Cg)-haloalkyt, {C+-Cs)-alkoxy, CN,

NO,, S(O),R? and NR''R'%;

R® is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-C4)-alkyl, (C1-C4)-haloalkyl and (C4-Cs)-alkoxy;

R'" and R* are each the same or different hydrogen, (C1-Cs)-alkyl or (C;-

Another preferred class of compounds of formula (1) are those in which:

R'is CN;

W is C-halogen;

R? is hydrogen or halogen;

R3 is CF; or OCF3;

R* is hydrogen, (C1-Cs)-alkyl or COR®;

A is (C4-Ce)-alkylene or (C-Cg)-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Cs)-cycloalkyl ring which is unsubstituted or oo : 23 substituted by one or more radicals selected from the group consisting of (Cs-

Ce)-alkyl and halogen; :

Ris (Ca-Ce)-cycloalkyl or ~{CH2)R’; or is (C4-Cg)-alkyl substituted by one or more : radicals selected from the group consisting of halogen, (C4-Ce)-alkoxy, (C1-Ce)- haloalkoxy, (C3-Cg)-cycloalkyl, S(O)R® and CO2-(C4-Cs)-alkyl; or when A is (C4-Cg)- ~ alkylene or (C4-Ce)-haloalkylene and RS is (C4-Cg)-alkyl substituted by one or more halogen radicals, one or more of the carbon atoms of R> may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;

R® is (C4-Cg)haloalkyl;

R%is (C4-Cs)-alkyl or (C4-Cg)-haloalkyl;

R” is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cg)-alkyl, (C1-Cg)-haloalkyl, (C4-Cg)-alkoxy, CN,

NO2, S(O),R® and NR'°R"";

R'" and R'' are each independently H, (C4-Cg)-alky! or (C;-Cs)-haloalkyl: n and p are each independently zero, one or two; and q is zero or one.

Another preferred class of compounds of formula (1) are those in which:

R'is CN; :

W is C-halogen;

R? is halogen;

R3 is CFs or OCF3; ~ R*is hydrogen, (C4-Cg)-alkyl or CORS;

A is (C4-Cg)-alkylene or (C4-Cq)-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Cs)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C;-

Ce)-alkyl and halogen;

Rois (C3-Cr)-cycioalkyl or {CH2)qR’; or is (C4-Ce)-alkyl substituted by one or more radicals selected from the group consisting of halogen, (C4-C3)-alkoxy, (C1-Ca)- haloalkoxy, (Ca-Cr)-cycloalkyl, S(O),R®, CN, NR'°R"?, S(O),R’, S(O),R®, OR and

ORY;

RS is (C4-C2)-haloalkyl;

] | 4

Ris phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-C,)-alkyl, (C1-C,4)-haloalkyl, (C1~Ca)-alkoxy, (Ci-Ca) haloalkoxy, CN, NO;, S(O),R®, COR", NR™®R" and OH;

R® is (C4-C4)-alkyl or (C4-C4)-haloalkyl;

R%is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C4-C4)-haloalkyl and (C4-C4)-alkoxy;

R' is H, (C1-Ca)-alkyl, (C4-Ca)-haloalkyl, (Ca-C4)-alkenyl, (C3-Cq)-alkynyi, (C3-Ce)-cycloalkyl, -(C1-Cg)-alkyl-(C3-Cg)-cycloalkyl or {CH,)R"; or

R'® and R'! together with the attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (C,-Cs)-alkyl;

R" and R" are each independently H, (C4-C3)-alkyl, (C1-Cs)-haloalkyl, (C3-Cg)-cycloalkyl or -(C4-C3)-alkyi-(C3-Cg)-cycloalkyl;

R'is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cj)-alkyl, (C4-C3)-haloalkyl, (C,-C3)-alkoxy, (C4-C3)- haloalkoxy, CN, NO,, S(0),R® and NR''R™; n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl in the above-mentioned radicals is independently a heteroaromatic radical having 5 or 6 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.

A further preferred class of compounds of formula (1) are those in which:

R'is CN;

Wis C-Cl, :

R? is chlorine;

R® is CF3 or OCF3; ~ R*is hydrogen, (C4-Ce)-alkyl or COR®,

A is (C-Ca)-alkylene:;

Claims

1. A method of controlling parasites in or on an animal comprising administering to the animal a parasiticidally effective amount of a 5-substituted- alkylaminopyrazole derivative of formula (1): RSS(O); R'

re. RS o-a-N NT R ZW NS R3 0) wherein: R'is CN; W is C-halogen or C-CHj3; R? is hydrogen, halogen or CH; : R® is (C1-Ca)-haloalkyl, (Ci-C3)-haloalkoxy or S(0),-(C1-Cz)-haloalkyt; R* is hydrogen, (C.-Ce)-alkenyl, (C2-Cg)-haloalkenyl, (C2-Ce)-alkynyl, (Co- Ce)-haloalkynyl, (Cs-C7)-cycloalkyl, CO-(CH,),-R’, COR®, CO-(CH,)4-R®, -CO-(Cs-

C.)-alkyl-(C1-Cg)-alkoxy, -CO,~(CH,)q-R”, -CO2R?, -CO2-(CH2)-R®, -CO-(Cs- C,)-cycloalkyl, -CO,-(C4-C4)-alkyl-(C3-C7)-cycloalkyl, -CO,-(C3-Cg)-alkenyl, -CO2-(Cs- Ce)-alkynyl, CONR'"R"!, .CH,R’, -CH,R®, OR’, OR® or OR®; or (C4-Cg)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkoxy, (C4-Cg)-haloalkoxy, (C3-C7)-cycloalkyl, S(0),R®, CO2-(C4-Cg)-alkyl, -O(C=0)-(C+-Cg)-alkyl, NR'°COR"?, NR"’R"", CONR™R", SO,NR'R"", OH, CN, NO,, OR’, NR'°SO,R®, COR® and OR?; A is (C4-C42)-alkylene or (C4-C42)-haloalkylene in which 2, 3 or 4 adjacent carbon : atoms optionally form part of a (C3-C)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C;- Ce)-alkyl and halogen; or is (C-C+2)-alkylene or (C4-C12)-haloalkylene in which last two mentioned groups a methylene moiety is replaced by a group selected from

-C(=0)-, -C(=NH)-, -O-, -S- and -NR"-, with the proviso that the replacing group is not bonded to the adjacent O or N atom: or is (C2-Ci2)-alkenylene or (C2~C2)- haloalkenylene;

Ris H, (Cs-Ce)-alkenyl, (C3-Ce)-haloalkenyl, (Ca-Ce)-alkynyl, (C3-Cg)-haloalkynyt, (C3-C7)-cycloalkyl, {{CH,)R’, «(CH2)R® or NR'R’; or is (C4-Cg)-alky! unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Ce)-alkoxy, (C4-Cs)-haloalkoxy, (Cs-Ce)-alkenyloxy, (C3-Ce)-haloalkenyloxy, (Cs- Ce)-alkynyloxy, (Cs-Ce)-haloalkynyloxy, (Cs-C7)-cycloalkyl, S(O),R®, CN, NO, OH, COR’, NR™COR'", NR'%SO,R®, CONR'R"', NR'’R"", 5(0),R’, S(O),R®, OR’, OR’ and CO2R'®; or when A is (C4-Cy,)-alkylene or (C1-C1)-haloalkylene and R® is (Cq- Ce)-alkyl unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R® may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;

R® is (C4-Cs)-alkyl, (C1-Ce)-haloalkyl, (Co-Cs)-alkenyl, (Co-Cg)-haloalkenyl, (Co- Ce)-alkynyl or (C2-Cg)-haloalkynyi; R’ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Ce)-alkyl, (C1-Cs)-haloalkyl, (C1-Cg)-alkoxy, (C1-Ce)- haloalkoxy, CN, NO,, S(0),R®, COR", COR'3, CONR'R"", SO,NR'°R"!, NR'’R"", OH, SO3H and (C4-Cs)-alkylideneimino; R83 is (C1-Cs)-alkyl or (C4-Cg)-haloalkyl; RY is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-C,)-alkyl, (C1-C4)-haloalkyl, (C4-C4)-alkoxy, (Cy- Ca)-haloalkoxy, NO, CN, CO»(C4-Cg)-alkyl, S(O),R®, OH and oxo; R' and R'? are each independently H, (C1-Cg)-alkyl, (C4-Cs)-haloalkyl, (C3-Ce)- alkenyl, (C3-Ce)-haloalkenyl, (C3-Ce)-alkynyl, (C3-Cs)-haloalkynyl, (C1-Ce)-cycloalkyl, -(C+-Ce)-alkyl-(C3-Cg)-cycloalkyl, {CH2)sR" or | CH2)R; or R'" and R'" and/or R'® and R'? each together with the respective attached N atom

: form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-Ce)-alkyl and (C,-Cg)-haloalkyl;

R' and R" are each independently H, (C+-Cg)-alkyl, (C;-Ce)-haloalkyl, (Cs-Cs)-cycloalkyl or {C4-Cg)-alkyl-(C3-Cg)-cycloalkyt; R'is phenyl unsubstituted or substituted by one or more radicals selected from the . | group consisting of halogen, (C4-Ce)-alkyl, (C1-Cg)-haloalkyl, (C4-Cg)-alkoxy, (C1-Cs)- haloalkoxy, CN, NO,, S(0),R® and NR''R™; R'is R" or «(CH,)R"; n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S; or a pesticidally acceptable salt thereof.

2. The method as claimed in claim 1, wherein the symbols and indices in formula (I) have the following meanings: - R'is CN; Wis C-CI; R? is chlorine; R3is CFs or OCF; R* is hydrogen, CO2-(C4-Cs)-alkyl, or (C1-Cs)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen and (Cs- Cj3)-alkoxy; A is (C+-Cs)-alkylene; R? is (C3-Cs)-cycloalkyl, —(CH2)R’, (C4-Ce)-alkyl or (C4-Cg)-haloalkyl; or when R® is (C4-Ce)-alkyl, one or more of the carbon atoms of the R® group may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring; R® is CF3, CF,Cl, CFCl,, CBrF, or CHF; : R’ is phenyl; n is zero, one or two; and . q is zero or one.

3. The method as claimed in claim 1, where the symbols and indices in formula (1) have the following meanings: R'is CN; W is C-halogen; R? is hydrogen or halogen; R® is CF3 or OCF3; R* is hydrogen, (C2-Ce)-alkenyl, (C2-Ce)-haloalkenyl, (C2-Cg)-alkynyl, (Co- Ce)-haloalkynyl, (C3-Cs)-cycloalkyl, -CO2-(C4-Cg)-alky! or -CHR’; or (C,-Ceg)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-Ce)-alkoxy, (C+-Cg)-haloalkoxy, (C3-Ce)-cycloalkyl, S(O),R® and CO2-(C4-Ce)-alkyl; A is (C4-Ce)-alkylene or (C,-Cg)-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Cs)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (Cs- Ce)-alkyl and halogen; R® is (C3-Cs)-cycloalkyl or ~(CHa)R’; or is (C4-Cg)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cg)- alkoxy, (C+-Cg)-haloalkoxy, (C3-Ce)-cycloalkyl, S(O),R? and CO»-(C1-Cg)-alkyl; or when A is (C4-Cg)-alkylene or (C4-Cg)-haloalkylene and RS is (C4-Cg)-alky! unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R® may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring; R® and R®are each independently (C1-Cg)-alkyl or (C1-Cg)-haloalky!; R’ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkyl, (C4-Cg)-haloalkyl, (C4-Cg)-alkoxy, CN, NO, S(0),R® and NR'°R""; R'* and R'" are each independently H, (C;-Ce)-alkyl or (C1-Cg)-haloalkyl; n and p are each independently zero, one or two; and q is zero or one.

4. 5-Substituted-alkylaminopyrazole derivatives of formula (1) as in claim 1, or pesticidally acceptable salts thereof, wherein:

~~ R'isCN; : W is C-halogen or C-CHj; : R? is hydrogen, halogen or CHa: . Riis (C1-Ca)-haloalkyl, (C4-Ca)-haloalkoxy or S(O),-(C4-Ca)-haloalkyl; R*is (C2-Ce)-alkenyl, (C2-Ce)-haloalkenyl, (C2-Cg)-alkynyl, (Co-Cs)-haloalkynyl, (Cs- Cr)-cycloalkyl, CO-(CHg)-R’, CO-(CH2)q-R®, -CO-(C4-Ca4)-alkyl-(C1-Cs)-alkoxy, -CO2(CHg)q-R’, -CO,R®, -CO2-(CHz)q-R®, -CO2-(C3-C7)-cycloalkyl, -CO2-(C1- Cy)-alkyl-(C3-C7)-cycloalkyl, -CO,~(C3-Cs)-alkenyl, -CO,~(C3-Ce)-alkynyl, CONR'R"", -CHZR’, -CH,R®, OR’, OR® or OR?; or (C+-Cg)-alky! which is substituted by one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkoxy, (C+- Ce)-haloalkoxy, (C3-C7)-cycloalkyl, S(O),R®, CO2-(C4-Ce)-alkyl, -O(C=0)-(C1-Cg)-alkyl, NR'° COR", NR'R"", CONR'"R", SO,NR'R"", OH, CN,

NO., OR’, NR'°SO,R?, COR® and OR®; Ais (C4-C12)-alkylene and (C4-C,z)-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Cg)-cycloalky! ring which is unsubstituted or ~ substituted by one or more radicals selected from the group consisting of (C;- Ce)-alkyl and halogen; or is (C1-Cz)-alkylene or (C4-C12)-haloalkylene in which last two mentioned groups a methylene moiety is replaced by a group selected from -C(=0)-, -C(=NH)-, -O-, -S- and -NR'>-, with the proviso that the replacing group is not bonded to the adjacent O or N atom; or is (C,-C42)-alkenylene or (C2-Cy2)- haloalkenylene; R® is H, (C3-Cg)-alkenyl, (C3-Ce)-haloalkenyl, (Ca-Cg)-alkynyl, (Ca-Cg)-haloalkynyl, (Cs-Cr)-cycloalkyl, {CH2)qR”, «(CH2)eR® or NR™R"; or is (C:-Cs)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Ce)-alkoxy, (C4-Cg)-haloalkoxy, (C3-Cg)-alkenyloxy, (C3-Cg)-haloalkenyloxy, (Cs-. Ce)-alkynyloxy, (C3-Cs)-haloalkynyloxy, (Cs-C7)-cycloalkyl, S(O),R%, CN, NO, OH, COR™, NR™COR'?, NR''SO,R® CONR'R"", NR"R", S(0),R”, S(0),R®, OR, OR® and CO.R'% or when A is (C4-C12)-alkylene or (C4-C42)-haloalkylene and Rois (Cs- Ce)-alkyl unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R® may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring;

R® is (C4-Cg)-alkyl, (C1-Ce)-haloalkyl, (C,-Cg)-alkenyl, (C2-Cg)-haloalkenyl, (Co- Ce)-alkynyl or (C2-Cg)-haloalkynyi; R’ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C+-Cg)-alkyl, (C4-Cs)-haloalkyl, (C4-Cg)-alkoxy, (C4-Ce)- haloalkoxy, CN, NO,, S(0),R®, COR'!, COR", CONRR"!, SO.NR"R"!, NR'R"", OH, SO;H and (C4-Cg)-alkylideneimino; R? is (C4-Cs)-alkyl or (C4-Ce)-haloalkyl: R%is heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Ca)-alkyl, (C1-C4)-haloaikyl, (C4-C,)-alkoxy, (C1- Ca)-haloalkoxy, NO,, CN, CO(C4-Ce)-alkyl, S(O),R®, OH and oxo; R' and R* are each independently H, (C4-Cq)-alkyl, (C1-Cg)-haloalkyl, (C3-Ce)- alkenyl, (Cs-Cs)-haloalkenyl, (C3-Cg)-alkynyl, (C3-Cs)-haloalkynyl, (C3-Cg)-cycloalkyl, -(C1-Ce)-alkyl-(C3-Cg)-cycloalkyl, (CH2)qR"® or «(CH,)qR®; or R' and R" and/or R' and R'? each together with the respective attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cs)-alkyl and (C4-Cs)-haloalkyl; R'" and R' are each independently H, (C1-Cg)-alkyl, (C1-Ce)-haloalkyl, (C3-Ce)-cycloalkyl or -(C4-Cg)-alkyl-(C3-Cg)-cycloalkyt; Ris phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Ce)-alkyl, (C1-Ceg)-haloalkyl, (C1-Cg)-alkoxy, (C1-Ce)- haloalkoxy, CN, NO,, S(O),R® and NR''R'*; R'is R" or {CH,)R"™; n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl! in the above-mentioned radicals is independently a heterocyclic : radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.

5. 5-Substituted-alkylaminopyrazole derivatives of formula (1) as in claim 1, or pesticidally acceptable salts thereof, wherein: :

R'is ON; W is C-halogen or C-CHj; R? is hydrogen, halogen or CHa: Ris (C1-Cs)-haloalkyt, (C4-C3)-haloalkoxy or S(O)p-(C4-C3)-haloalky!; R* is hydrogen, (C+-Ce)-alkyl or CORE; A is (C1-Cy2)-alkylene and (C4-Ci2)-haloalkylene in which 2, 3 or 4 adjacent carbon atoms optionally form part of a (C3-Cg)-cycloalkyl ring which is unsubstituted or substituted by one or more radicals selected from the group consisting of (C+- Ce)-alkyl and halogen; or is (C4-C4z)-alkylene or (C4-C1z)-haloalkylene in which last two mentioned groups a methylene moiety is replaced by a group selected from -C(=0)-, -C(=NH)-, -O-, -S- and -NR'°-, with the proviso that the replacing group is not bonded to the adjacent O or N atom; or is (C,-C12)-alkenylene or (C,-Cy2)- haloalkenylene; Ris H, (Cs-Ce)-alkenyl, (C3-Cg)-haloalkenyl, (C3-Cg)-alkynyl, (C3-Ce)-haloalkynyt, (C3-Cr)-cycloalkyl, {CHg)R", «(CH2)qR® or NR'R'; or is (C,-Ce)-alkyl substituted by one or more radicals selected from the group consisting of halogen, (C1-Cs)- alkoxy, (C1-Ce)-haloalkoxy, (C3-Cs)-alkenyloxy, (C3-Cs)-haloalkenyloxy, (C3-Ce)- alkynyloxy, (C3-Ce)-haloalkynyloxy, (Cs-Cr)-cycloalkyl, S(O),R®, CN, NO,, OH, COR'®, NR"COR', NR'’SO,R®, CONR'R!, NR'R™, $(0),R’, S(O),R®, OR’, OR® and COR; or when A is (C4-Ci)-alkylene or (C1-C12)-haloalkylene and R® is (C1- Ce)-alkyl unsubstituted or substituted by one or more halogen radicals, one or more of the carbon atoms of R® may, together with O and one or more of the carbon atoms of A, form a 5- or 6-membered ring; R® is (C1-Cg)-haloalkyl; R’ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cg)-alkyl, (C4-Cg)-haloalkyl, (C4-Ce)-alkoxy, (C1-Ce)- haloalkoxy, CN, NO, S(0),R®, COR", COR'3, CONR™R"!, SO,NR'°R", NR"R'", OH, SO3H and (C4-Cg)-alkylideneimino: R® is (C4-Cs)-alkyl or (C4-Cg)-haloalkyl: "Ris heterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-Cy)-alkyl, (C4-C4)-haloalkyl, (C1-C4)-alkoxy, (C4-

C.)-haloalkoxy, NO2, CN, CO,(C+-Ce)-alkyl, S(O),R®, OH and oxo;

oo : 68 R'® and R' are each independently H, (C1-Ce)-alkyl, (Ci-Ce)-haloalkyl, (C5-Ce)- alkenyl, (C3-Ce)-haloalkenyl, (Cs-Ce)-alkynyl, (C3-Ce)-haloalkyny!, (Cs-Cs)-cycloalkyl, -(C1-Cé)-alkyl-(C3-Ce)-cycloalkyl, (CH2)qR"® or ~(CH,)R®; or R'® and R"" and/or R™ and R'? each together with the respective attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C4-Cg)-alkyl and (C4-C¢)-haloalkyl; R'" and R' are each independently H, (C;-Cg)-alkyl, (C1-C)-haloalkyl, (C3-Ceg)-cycloalkyl or -(C4-Cg)-alkyl-(C3-Cs)-cycloalkyl; R"is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C-Cg)-alkyl, (C4-Cg)-haloalkyl, (C4-Cg)-alkoxy, (C1-Cs)- haloalkoxy, CN, NO,, S(0),R® and NR''R™: R'is R' or (CH2)qR"; n and p are each independently zero, one or two; - q is zero or one; and each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S.

6. 5-Substituted-alkylaminopyrazole derivatives of formula (1), or pesticidally ‘acceptable salts thereof, wherein: R" is CN; R? is chlorine; R® is CF3 or OCF3; W is C-Cl; R* is hydrogen or (C4-C)- alkyl; R® is (C1-Ce)-alkyl; R® is CF3; A is (Co-Cs)-alkylene and n is zero, one or two.

7. The use of compounds of formula (I) or pesticidally acceptable salts thereof according to one or more of claims 1 to 6 for the control of parasites in and on ‘ animals. .

8. The use of compounds of formula (1) or pesticidally acceptable salts thereof according to one or more of claims 1 to 6 for preparing a veterinary medicament.

9. A pesticidal composition comprising a compound of formula (I) or a pesticidally acceptabie salt thereof as defined in any one of claims 1 to 6, in association with a pesticidally acceptable diluent or carrier and/or surface active agent.

10. A process for the preparation of a compound of formula (1) or a salt thereof as defined in claim 1 to 6, which process comprises: a) where R', R? R® R® W, A and n are as defined in claim 1, R* and R® are as defined in claim 1 with the exclusion of hydrogen, and R* is H, reacting a compound of formula (I): ReS(0), R! I ] L Nh R ZW “ R3 (0) wherein R', R?, R®, R®, W and n are as defined in claim 1, and L is a leaving group, with a compound of formula (111): R>—O0—A—NH, (nn) wherein A is as defined in claim 1 and Ris as defined in claim 1 with the exclusion of hydrogen; or b) where R', R% R® R* R®, W, A and n are as defined in claim 1 and R* and R® are as defined in claim 1 with the exclusion of hydrogen, OR’, OR® and OR®, and R® : is as defined in claim 8 with the exclusion of hydrogen, reacting a compound of formula (IV):

RSS(0). R' . wo 0 R ~ N _N : Nop” 'N R Aw : “ R3 (IV) wherein R', R?, R3, R®, W, A and n are as defined in claim 1 and R® is as defined in claim 1 with the exclusion of hydrogen, with a compound of formula (V): RL (V) wherein R4 is as defined in claim 1 with the exclusion of hydrogen, OR’, OR® and OR®, and L' is a leaving group; or c) where R', R% R® R% R% W, A and n are as defined in claim 1 and RS is as defined in claim 1 with the exclusion of hydrogen, reacting a compound of formula (VI): R6S(0), R? wo ILI Re Ng R Zz w NN Rs (VI) wherein R', R% R® R* R®, W and n are as defined in claim 1, with a compound of formula (VII): R-0-A-L? (Vi) wherein A is as defined in claim 1, R® is as defined in claim 1 with the exclusion of hydrogen and L? is a leaving group; or }

d) where R', R% R% R®, W and n are as defined in claim 1, R® is as defined in claim 1 with the exclusion of hydrogen, R* is hydrogen and A is -CH,-, reacting a . compound of formula (VIl): eon ~R! HN NN R Za, “ Ls (Vii) wherein R', R?, R3, R®, Wand n are as defined in claim 1, with a mixture of formaldehyde and a compound of formula (IX): R’-0-H (1X) wherein R® is as defined in claim 1 with the exclusion of hydrogen; or e). where R',R% R3 R* R® A, W and n are as defined in claim 1, and R% is as defined in claim 1 with the exclusion of hydrogen, reacting a compound of formula (X): R8S(0), R rel I! ~N “ HO—A N So

-. R3 xX) wherein R', R%, R3, RY, A, W and'n are as defined in claim 1, with a compound of formula (XI): : RL? (XI)

wherein R® is as defined in claim 1 with the exclusion of hydrogen and L3 is a leaving group; or f) where R', R?, R3, R%, R®, R®, A, W and n are as defined in claim 1, reacting a compound of formula (Xi): R8S(O); R! re _N NY Li—A ANS R3 (Xi) wherein R', R2, R®, R%, A, W and n are as defined in claim 1 and L*is aleaving group, with a compound of formula (1X) as defined above; and a) if desired, converting a resulting compound of formula (1) into a pesticidally acceptable salt thereof.

11. The method as claimed in claim 1, substantially as herein described and exemplified and/or described with reference to the examples.

12. The use as claimed in claim 7, substantially as herein described and exemplified and/or described with reference to the examples.

13. The composition as claimed in claim 9, substantially as herein described and exemplified and/or described with reference to the examples.

14. The process as claimed in claim 10, substantially as herein described and exemplified and/or described with reference to the examples. AMENDED SHEET