WO2015169723A1

WO2015169723A1 - Insecticidal compounds based on thiophene derivatives

Info

Publication number: WO2015169723A1
Application number: PCT/EP2015/059661
Authority: WO
Inventors: Girish RAWAL; Rupesh PATRE; Jérôme Yves CASSAYRE; Guillaume Berthon; Myriem El Qacemi
Original assignee: Syngenta Participations AG
Current assignee: Syngenta Participations AG
Priority date: 2014-05-09
Filing date: 2015-05-04
Publication date: 2015-11-12
Anticipated expiration: 2016-11-09

Abstract

The present invention provides compounds of formula (I), wherein P is selected from P1 and P2, or P and A¹ = C-R⁵ together are P3 and wherein the substituents A¹, A², A³, A⁴, G¹, G², G³, R¹, R², R³, R⁴, R⁵, R^6a, R^6b, R⁷, R⁸, R⁹, R¹⁰, R¹¹ and p are as defined in the claims. The invention also relates to processes and intermediates for preparing these compounds, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these compounds and to methods of using these compounds to control insect, acarine, nematode and mollusc pests.

Description

INSECTICIDAL COMPOUNDS BASED ON THIOPHENE DERIVATIVES

The present invention relates to certain arylthioacetamides and derivatives thereof, to processes and intermediates for preparing these compounds, to insecticidal, acaricidal, nematicidal and molluscicidal compositions comprising these compounds and to methods of using these compounds to control insect, acarine, nematode and mollusc pests.

Certain compounds with insecticidal properties are disclosed, for example, in JP2007106756. However there is a continuing need to find new biologically active compounds as well as new biologically active compounds displaying superior properties for use as agrochemical active ingredients, for example greater biological activity, different spectrum of activity, increased safety profile, or increased biodegradability.

In a first aspect the invention provides compounds of formula I)

wherein

P is selected from P1 and P2, or P and A¹ = C-R⁵ together are P3

P1 P2 P3

A¹, A², A³,and A⁴ are independently of each other C-H, C-R⁵, or nitrogen;

G is oxygen or sulfur;

G² is oxygen or sulfur;

G³ is oxygen or sulfur;

R is hydrogen, d-C₈alkyl, d-C₈alkoxy, Ci-C₈alkylcarbonyl, or d-C₈alkoxycarbonyl;

R² is Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃-Ci₀cycloalkyl substituted by one to five R ³, C₃-Ci₀cycloalkyl-Ci-C₄alkylene or C₃-Ci₀cycloalkyl-Ci-C₄alkylene substituted by one to five R ³, aryl-Ci-C₄alkylene- or aryl-Ci-C₄alkylene- substituted by one to five R ⁴, heterocyclyl-Ci-C₄alkylene- or heterocyclyl-Ci-C₄alkylene- substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴, d- C₈alkylaminocarbonyl-Ci-C₄alkylene, Ci-C₈haloalkylaminocarbonyl-Ci-C₄alkylene, C₃-C₈cycloalkyl- aminocarbonyl-C-rd alkylene, aryl-CH₂-aminocarbonyl-d-C₄alkylene or aryl-CH₂-aminocarbonyl-d- dalkylene wherein the aryl is substituted by one to five R ⁴, Ci-C₈alkylaminocarbonyl, d- Cshaloalkylaminocarbonyl, C₃-C₆cycloalkylaminocarbonyl, d-C₆alkyl-0-N=CH-, or d-C₆haloalkyl-0- N=CH-; „

-2-

R³ is d-Cshaloalkyl;

R⁴ is aryl or aryl substituted by one to five R ⁵, or heteroaryl or heteroaryl substituted by one to five R ⁵;

each R⁵ is independently hydrogen, halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, d- C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₃-Ci₀cycloalkyl, Ci-C₈alkoxy, d- C₈haloalkoxy, Ci-C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, d- C₈alkylsulfonyl, or Ci-C₈haloalkylsulfonyl, or two R⁵ on adjacent carbon atoms together form a -CH=CH- CH=CH- bridge or a -N=CH-CH=CH- bridge;

R^6a and R^6b are each independently hydrogen, halogen, cyano, Ci-C₈alkyl, Ci-C₈haloalkyl, or C₃- Cscycloalkyl, or R^6a and R^6b together with the carbon atom to which they are attached may form a 3 to 6- membered carbocyclic ring;

R⁷ is hydrogen, Ci-C₈alkyl, Ci-C₈alkoxy, Ci-C₈alkylcarbonyl, or Ci-C₈alkoxycarbonyl;

R⁸ is Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃-Ci₀cycloalkyl substituted by one to five R ³, C₃-Ci₀cycloalkyl-Ci-C₄alkylene or C₃-Ci₀cycloalkyl-Ci-C₄alkylene substituted by one to five R ³, aryl-Ci-C₄alkylene- or aryl-Ci-C₄alkylene- substituted by one to five R ⁴, heterocyclyl-Ci-C₄alkylene- or heterocyclyl-Ci-C₄alkylene- substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, or heterocyclyl or heterocyclyl substituted by one to five R ⁴, R⁹ is hydrogen, Ci-C₈alkyl, Ci-C₈alkoxy, Ci-C₈alkylcarbonyl, or Ci-C₈alkoxycarbonyl;

R ⁰ is Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃-Ci₀cycloalkyl substituted by one to five R ³, C₃-Ci₀cycloalkyl-Ci-C₄alkylene or C₃-Ci₀cycloalkyl-Ci-C₄alkylene substituted by one to five R ³, aryl-Ci-C₄alkylene- or aryl-Ci-C₄alkylene- substituted by one to five R ⁴, heterocyclyl-Ci-C₄alkylene- or heterocyclyl-Ci-C₄alkylene- substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴;

each R is independently halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, C₂-C₈alkenyl, C₂- Cshaloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, hydroxy, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, d- C₈haloalkylsulfonyl, Ci-C₈alkylcarbonyl, or Ci-C₈alkoxycarbonyl;

each R ² is independently halogen, cyano, nitro, hydroxy, amino, Ci-C₈alkylamino, (d- C₈alkyl)₂amino, Ci-C₈alkylcarbonylamino, Ci-C₈haloalkylcarbonylamino, d-C₈alkoxy, Ci-C₈haloalkoxy, aryloxy or aryloxy substituted by one to five R ⁶, aryloxy-d-dalkylene or aryloxy-d-dalkylene wherein the aryl moiety is substituted by one to five R ⁶, d-C₈alkylcarbonyl, d-C₈alkoxycarbonyl, mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, d-dalkylsulfinyl, Ci-C₈haloalkylsulfinyl, d-dalkylsulfonyl, d- C₈haloalkylsulfonyl, aryl-d-dalkylthio or aryl-d-dalkylthio wherein the aryl moiety is substituted by one to five R ⁶;

each R ³ is independently halogen, cyano, d-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, or d-dalkoxy,

Crdakoxycarbonyl, or two R ³ are together R ⁹-0-N=;

each R ⁴ is independently halogen, cyano, nitro, d-C₈alkyl, Ci-C₈haloalkyl, Ci-C₈cyanoalkyl, C₂-

C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₃-d₀cycloalkyl, C₃-Ciocycloalkyl-Ci- dalkylene, hydroxy, d-dalkoxy, d-C₈haloalkoxy, mercapto, d-dalkylthio, d-dhaloalkylthio, d- C₈alkylsulfinyl, d-C₈haloalkylsulfinyl, d-C₈alkylsulfonyl, Ci-C₈haloalkylsulfonyl, Ci-C₈alkylaminosulfonyl,

(Ci-C₈alkyl)₂aminosulfonyl, Ci-C₈alkylcarbonyl, Ci-C₈haloalkylcarbonyl, Ci-C₈alkoxycarbonyl, C₈haloalkoxycarbonyl, aryl or aryl substituted by one to five R ⁶, heterocyclyl or heterocyclyl substituted by one to five R ⁶, aryl-Ci-C₄alkylene or aryl-Ci-C₄alkylene wherein the aryl moiety is substituted by one to five R ⁶, heterocyclyl-Ci-C₄alkylene or heterocyclyl-Ci-C₄alkylene wherein the heterocyclyl moiety is substituted by one to five R ⁶, aryloxy or aryloxy substituted by one to five R ⁶, or aryloxy-Ci-C₄alkylene or aryloxy-Ci-C₄alkylene wherein the aryl moiety is substituted by one to five R ⁶ or two R ⁴ are together =0; each R ⁵ is independently halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, C₂-C₈alkenyl, C₂- C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, hydroxy, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, d- C₈haloalkylsulfonyl, Ci-C₈alkylcarbonyl, or Ci-C₈alkoxycarbonyl;

each R ⁶ is independently halogen, cyano, nitro, Ci-C₄alkyl, Ci-C₄haloalkyl, Ci-C₄alkoxy, or d-

C₄haloalkoxy;

each R ⁹ is hydrogen, Ci-C₈alkyl or Ci-C₈haloalkyl;

each Z is independently halogen, cyano, Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², nitro, hydroxyl, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, Ci-C₈alkylthio, Ci-C₈haloalkylthio, d- C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, or Ci-C₈haloalkylsulfonyl;

n is 1 or 2;

p is 0, 1 , 2, 3, 4, or 5;

or a salt or A/-oxide thereof.

In a second aspect the invention provides compounds of formula I

wherein

P is selected from P1 and P2, or P and A¹ = C-R^5b together are P3

P1 P2 P3

A¹ is C-R^5b;

A², A³ and A⁴ are independently of one another C-H, C-R^5a or nitrogen;

G is oxygen or sulfur;

G² is oxygen or sulfur;

G³ is oxygen or sulfur;

R is hydrogen, Ci-C₈alkyl, Ci-C₈alkoxy, Ci-C₈alkylcarbonyl, or Ci-C₈alkoxycarbonyl; R² is Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃-Ci₀cycloalkyl substituted by one to five R ³, C₃-Ci₀cycloalkyl-Ci-C₄alkylene or C₃-Ci₀cycloalkyl-Ci-C₄alkylene substituted by one to five R ³, aryl-Ci-C₄alkylene- or aryl-Ci-C₄alkylene- substituted by one to five R ⁴, heterocyclyl-Ci-C₄alkylene- or heterocyclyl-Ci-C₄alkylene- substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴, d-

C₈alkylaminocarbonyl-Ci-C₄alkylene, Ci-C₈haloalkylaminocarbonyl-Ci-C₄alkylene, C₃-C₈cycloalkyl- aminocarbonyl-Ci-C₄ alkylene, aryl-CH₂-aminocarbonyl-Ci-C₄alkylene or aryl-CH₂-aminocarbonyl-d- C₄alkylene wherein the aryl is substituted by one to five R ⁴, Ci-C₈alkylaminocarbonyl, d- C₈haloalkylaminocarbonyl, C₃-C₆cycloalkylaminocarbonyl,

or d-C₆haloalkyl-0- N=CH-;

R³ is d-Cshaloalkyl;

each R^5a is independently hydrogen, halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, d- C₈alkenyl, d-dhaloalkenyl, d-dalkynyl, d-dhaloalkynyl, d-docycloalkyl, d-C₈alkoxy, d- dhaloalkoxy, d-dalkylthio, d-dhaloalkylthio, d-C₈alkylsulfinyl, d-dhaloalkylsulfinyl, d- dalkylsulfonyl, or d-C₈naloalkylsulfonyl, or two R⁵ on adjacent carbon atoms together form a -CH=CH- CH=CH- bridge or a -N=CH-CH=CH- bridge

each R^5b is independently halogen, cyano, nitro, d-C₈alkyl, d-C₈haloalkyl, d-dalkenyl, C₂- Cshaloalkenyl, C₂-C₈alkynyl, d-dhaloalkynyl, d-docycloalkyl, d-dalkoxy, d-dhaloalkoxy, d- dalkylthio, d-dhaloalkylthio, d-dalkylsulfinyl, d-C₈naloalkylsulfinyl, d-dalkylsulfonyl, or d- dhaloalkylsulfonyl, or two R⁵ on adjacent carbon atoms together form a -CH=CH-CH=CH- bridge or a - N=CH-CH=CH- bridge

R^6a and R^6b are each independently hydrogen, halogen, cyano, d-C₈alkyl, d-dhaloalkyl, or C₃- dcycloalkyl, or R^6a and R^6b together with the carbon atom to which they are attached may form a 3 to 6- membered carbocyclic ring;

R⁷ is hydrogen, d-C₈alkyl, d-C₈alkoxy, d-dalkylcarbonyl, or d-C₈alkoxycarbonyl;

R⁸ is d-dalkyl or d-C₈alkyl substituted by one to five R ², d-Ci₀cycloalkyl or C₃-d₀cycloalkyl substituted by one to five R ³, d-Ci₀cycloalkyl-d-dalkylene or d-Ci₀cycloalkyl-d-dalkylene substituted by one to five R ³, aryl-d-dalkylene- or aryl-d-dalkylene- substituted by one to five R ⁴, heterocyclyl-d-C₄alkylene- or heterocyclyl-Ci-dalkylene- substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, or heterocyclyl or heterocyclyl substituted by one to five R ⁴, each R^! is independently hydrogen, d-C₈alkyl, d-C₈alkoxy, d-C₈alkylcarbonyl, or d-dalkoxycarbonyl;

R ⁰ is d-C₈alkyl or d-dalkyl substituted by one to five R ², C₃-d₀cycloalkyl or d-Ci₀cycloalkyl substituted by one to five R ³, C₃-d₀cycloalkyl-d-C₄alkylene or d-Ci₀cycloalkyl-d-dalkylene substituted by one to five R ³, aryl-d-dalkylene- or aryl-d-dalkylene- substituted by one to five R ⁴, heterocyclyl-Ci-dalkylene- or heterocyclyl-d-C₄alkylene- substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴;

each R is independently halogen, cyano, nitro, d-C₈alkyl, d-C₈haloalkyl, d-dalkenyl, C₂- dhaloalkenyl, d-dalkynyl, d-dhaloalkynyl, hydroxy, d-C₈alkoxy, d-dhaloalkoxy, mercapto, Ci- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, d- C₈haloalkylsulfonyl, Ci-C₈alkylcarbonyl, or Ci-C₈alkoxycarbonyl;

each R ² is independently halogen, cyano, nitro, hydroxy, amino, Ci-C₈alkylamino, (d- C₈alkyl)₂amino, Ci-C₈alkylcarbonylamino, Ci-C₈haloalkylcarbonylamino, Ci-C₈alkoxy, Ci-C₈haloalkoxy, aryloxy or aryloxy substituted by one to five R ⁶, aryloxy-Ci-C₄alkylene or aryloxy-Ci-C₄alkylene wherein the aryl moiety is substituted by one to five R ⁶, Ci-C₈alkylcarbonyl, Ci-C₈alkoxycarbonyl, mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, d- C₈haloalkylsulfonyl, aryl-Ci-C₄alkylthio or aryl-Ci-C₄alkylthio wherein the aryl moiety is substituted by one to five R ⁶;

each R ³ is independently halogen, cyano, Ci-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, or Ci-C₈alkoxy,

Ci-C₈akoxycarbonyl, or two R ³ are together R ⁹-0-N=;

each R ⁴ is independently halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, Ci-C₈cyanoalkyl, C₂- C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₃-Ci₀cycloalkyl, C₃-Ci₀cycloalkyl-Ci- C₄alkylene, hydroxy, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, Ci-C₈alkylthio, Ci-C₈haloalkylthio, d- C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, Ci-C₈haloalkylsulfonyl, Ci-C₈alkylaminosulfonyl, (Ci-C₈alkyl)₂aminosulfonyl, Ci-C₈alkylcarbonyl, Ci-C₈haloalkylcarbonyl, Ci-C₈alkoxycarbonyl,

Cshaloalkoxycarbonyl, aryl or aryl substituted by one to five R ⁶, heterocyclyl or heterocyclyl substituted by one to five R ⁶, aryl-Ci-C₄alkylene or aryl-Ci-C₄alkylene wherein the aryl moiety is substituted by one to five R ⁶, heterocyclyl-Ci-C₄alkylene or heterocyclyl-Ci-C₄alkylene wherein the heterocyclyl moiety is substituted by one to five R ⁶, aryloxy or aryloxy substituted by one to five R ⁶, or aryloxy-Ci-C₄alkylene or aryloxy-Ci-C₄alkylene wherein the aryl moiety is substituted by one to five R ⁶ or two R ⁴ are together =0; each R ⁵ is independently halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, C₂-C₈alkenyl, C₂- C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, hydroxy, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, d- Cshaloalkylsulfonyl, Ci-C₈alkylcarbonyl, or d-C₈alkoxycarbonyl;

each R ⁶ is independently halogen, cyano, nitro, Ci-C₄alkyl, Ci-C₄haloalkyl, Ci-C₄alkoxy, or d- C₄haloalkoxy;

each R ⁹ is hydrogen, Ci-C₈alkyl or Ci-C₈haloalkyl;

n is 1 or 2;

p is 0, 1 , 2, 3, 4, or 5;

or a salt or A/-oxide thereof.

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.

The compounds of the invention may contain one or more asymmetric carbon atoms, for example, in the -CR³R⁴- group and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such. Further, where any group is SO, the compounds of the invention are sulfoxides, which can also exist in two enantiomeric forms.

The number of substituents does not exceed the number of available C-H and N-H bonds, for example in the group Ci-C₈alkyl substituted by one to five R ² has only one to three substituents if dalkyl thus methyl is meant.

Alkyl groups (either alone or as part of a larger group, such as alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl or alkoxycarbonyl) can be in the form of a straight or branched chain and are, for example, methyl, ethyl, propyl, prop-2-yl, butyl, but-2-yl, 2-methyl-prop-1-yl or 2-methyl-prop-2-yl. The alkyl groups are preferably Ci-C₆, more preferably C1-C4, most preferably C1-C3 alkyl groups. Where an alkyl moiety is said to be substituted , the alkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.

Alkylene groups can be in the form of a straight or branched chain and are, for example, -CH₂- , -CH2-CH2-, -CH(CH₃)-, -CH2-CH2-CH2-, -CH(CH₃)-CH₂- or -CH(CH₂CH₃)-. The alkylene groups are preferably Ci-C₃, more preferably C1-C2, most preferably Ci alkylene groups.

Alkenyl groups can be in the form of straight or branched chains, and can be, where appropriate, of either the (E)- or (Z)-configu ration. Examples are vinyl and allyl. The alkenyl groups are preferably C₂- C₆, more preferably C₂-C₄, most preferably C₂-C₃ alkenyl groups.

Alkynyl groups can be in the form of straight or branched chains. Examples are ethynyl and propargyl. The alkynyl groups are preferably C₂-C₆, more preferably C₂-C₄, most preferably C₂-C₃ alkynyl groups.

Halogen is fluorine, chlorine, bromine or iodine.

Haloalkyl groups (either alone or as part of a larger group, such as haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl) are alkyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, difluoromethyl, trifluoromethyl, chlorodifluoromethyl or 2,2,2-trifluoro-ethyl.

Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or 1 ,2-dichloro-2-fluoro-vinyl.

Haloalkynyl groups are alkynyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 1-chloro-prop-2-ynyl.

Cycloalkyl groups or carbocyclic rings can be in mono- or bi-cyclic form and are, for example, cyclopropyl, cyclobutyl, cyclohexyl and bicyclo[2.2.1]heptan-2-yl. The cycloalkyl groups are preferably C₃- C₈, more preferably C₃-C₆ cycloalkyl groups. Where a cycloalkyl moiety is said to be substituted, the cycloalkyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.

Aryl groups (either alone or as part of a larger group, such as aryl-alkylene) are aromatic ring systems which can be in mono-, bi- or tricyclic form. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, phenyl being most preferred. Where an aryl moiety is said to be substituted, the aryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.

Heteroaryl groups (either alone or as part of a larger group, such as heteroaryl-alkylene) are aromatic ring systems containing at least one heteroatom and consisting either of a single ring or of two or more fused rings. Preferably, single rings will contain up to three heteroatoms and bicyclic systems up to four heteroatoms which will preferably be chosen from nitrogen, oxygen and sulfur. Examples of monocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g. 1.2.4 triazoyi), furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl. Examples of bicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl. Monocyclic heteroaryl groups are preferred, pyridyl being most preferred. Where a heteroaryl moiety is said to be substituted, the heteroaryl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.

Heterocyclyl groups or heterocyclic rings (either alone or as part of a larger group, such as heterocyclyl-alkylene) are defined to include heteroaryl groups and in addition their unsaturated or partially unsaturated analogues. Examples of monocyclic groups include isoxazolyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, [1 ,3]dioxolanyl, piperidinyl, piperazinyl, [1 ,4]dioxanyl, and morpholinyl or their oxidised versions such as 1-oxo-thietanyl and 1 ,1-dioxo-thietanyl. Examples of bicyclic groups include 2,3-dihydro- benzofuranyl, benzo[1 ,4]dioxolanyl, benzo[1 ,3]dioxolanyl, chromenyl, and 2,3-dihydro-benzo[1 ,4]dioxinyl. Where a heterocyclyl moiety is said to be substituted, the heterocyclyl moiety is preferably substituted by one to four substituents, most preferably by one to three substituents.

Preferred values of P1 , P2, P3, A¹, A², A³, A⁴, G , G², G³, R , R², R³, R⁴, R⁵, , R^6a, R^6b, R⁷, R⁸, R⁹ , R ⁰ , R¹¹, R ², R ³, R ⁴, R ⁵, R ⁶, R ⁷, R ⁸, R ⁹, R²⁰, k, n, p, and q are, in any combination (including combinations of preferred values with the original values) as set out below.

Preferably no more than two of A², A³ and A⁴ are nitrogen.

Preferably A² is C-H, C-R^5a or N, more preferably A² is C-H or C-R^5a, most preferably A² is C-H.

Preferably A³ is C-H or N, most preferably A³ is C-H.

Preferably A⁴ is C-H or N, most preferably A⁴ is C-H.

In one group of compounds A², A³ and A⁴ are C-H or N, wherein no more than two of A², A³ and A⁴ are N and wherein A³ and A⁴ are not both N. Preferably A² is C-H and A³ and A⁴ are C-H or one of A³ and A⁴ is N. More preferably A², A³ and A⁴ are C-H.

Preferably G is oxygen.

Preferably G² is oxygen.

Preferably G³ is oxygen.

Preferably G , G² and G³ are oxygen.

Preferably R is hydrogen, methyl, ethyl, methylcarbonyl, or methoxycarbonyl, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.

Preferably R² is d-C₈alkyl or d-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃- docycloalkyl substituted by one to five R ³, C₃-C₁₀cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₁₀cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- or heterocyclyl-C(R ⁷)(R¹⁸)- wherein the heterocyclyl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴, Ci-C₈alkylaminocarbonyl-CH₂-, Ci-C₈haloalkylaminocarbonyl- CH₂-, C₃-C₈cycloalkylaminocarbonyl-CH₂-, aryl-CH₂-aminocarbonyl-CH₂- or aryl-CH₂-aminocarbonyl-CH₂- wherein the aryl is substituted by one to five R ⁴, Ci-C₈alkylaminocarbonyl, Ci-C₈haloalkylaminocarbonyl, C₃-C₆cycloalkylanriinocarbonyl,

wherein heterocyclyl is a 4 to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, SO, S0₂, N, and N(R²⁰) as ring atoms.

wherein aryl is phenyl;

wherein R ⁷ and R ⁸ are independently hydrogen, cyano, halogen, Ci-C₄alkyl, Ci-C₄haloalkyl, d- C₄alkoxy, Ci-C₄haloalkoxy or C₃-C₆cycloalkyl;

or R ⁷ and R ⁸ together form a three to six membered carbocycle;

and wherein R²⁰ is hydrogen or R ⁴.

More preferably R² is Ci-C₆alkyl or Ci-C₆alkyl substituted by one to five R ², C₃-C₈cycloalkyl or

C₃-C₈cycloalkyl substituted by one to five R ³, C₃-C₈cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₈cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)-, aryl or aryl substituted by one to five R ⁴, heterocyclyl, Ci-C₆alkylaminocarbonyl-CH₂-, Ci-C₆haloalkylaminocarbonyl-CH₂-, C₃-C₈cycloalkyl- aminocarbonyl-CH₂-, aryl-CH₂-aminocarbonyl-CH₂- or aryl-CH₂-aminocarbonyl-CH₂- wherein the aryl is substituted by one to five R ⁴, Ci-C₆alkylaminocarbonyl, Ci-C₆haloalkylaminocarbonyl, C₃- C₆cycloalkylaminocarbonyl-,

or CrC₄haloalkyl-0-N=CH-;

wherein heterocyclyl is a 4- to 6-membered saturated or partially saturated heterocyclic ring containing one or two heteroatoms independently selected from O, S, SO, S0₂, N and N(R²⁰) as ring atoms, wherein one or two carbon ring atoms are optionally substituted by oxo, and wherein the ring is optionally substituted by one or two R ⁴,

or heterocyclyl is a 5- or 6-membered heteroaryl ring containing one to three heteroatoms selected from O, N and S as ring atoms, wehrein the ring is optionally substituted by one to three R ⁴; wherein aryl is phenyl;

wherein R ⁷ is hydrogen or Ci-C₄alkyl;

wherein R ⁸ is independently hydrogen, cyano, halogen, Ci-C₄alkyl, Ci-C₄haloalkyl, Ci-C₄alkoxy, Ci-C₄haloalkoxy or C₃-C₆cycloalkyl;

or R ⁷ and R ⁸ together form a 3- to 6-membered carbocycle;

and wherein R²⁰ is hydrogen or R ⁴.

C₃-C₈cycloalkyl substituted by one to five R ³, C₃-C₈cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₈cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, heterocyclyl, Ci-C₆alkylaminocarbonyl-CH₂-, Ci-C₆haloalkylaminocarbonyl-CH₂-, C₃-C₈cycloalkyl- aminocarbonyl-CH₂-, aryl-CH₂-aminocarbonyl-CH₂- or aryl-CH₂-aminocarbonyl-CH₂- wherein the aryl is substituted by one to five R ⁴, Ci-C₆alkylaminocarbonyl-, C₃-C₆cycloalkylaminocarbonyl-, Ci-C₄alkyl-0- N=CH-, or d-C₄haloalkyl-0-N=CH-;

wherein heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0₂ as ring atoms, wherein the ring is optionally substituted by one or two methyl; or heterocyclyl is a 5 or 6-membered saturated or partially saturated heterocyclic ring containing one or two heteroatoms selected from N(R²⁰), N, S and O as ring atoms, wherein one or two carbon ring atoms are optionally substituted by oxo;

or heterocycyl is a 6-membered heteroaryl ring containing one to three heteroatoms selected from O, N and S as ring atoms, wehrein the ring is optionally substituted by one to three groups independently selected from halogen, cyano, Ci-C₄alkyl, Ci-C₄haloalkyl, d-C₄alkoxy, Ci-C₄haloalkoxy and C₃-C₆cycloalkyl;

wherein each R ² is independently halogen, d-C₈alkoxy, Ci-C₈haloalkoxy-mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, or d- Cshaloalkylsulfonyl;

wherein each R ³ is independently halogen, cyano, d-dalkyl, or two R ³ are together R ⁹-0-N=; wherein each R ⁴ is independently halogen, cyano, nitro, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, or d-dhaloalkoxy;

wherein R ⁷ is hydrogen or d-dalkyl;

wherein R ⁸ is independently hydrogen, cyano, halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy or C₃-C₆cycloalkyl;

or R ⁷ and R ⁸ together form a three to six membered carbocycle;

wherein R ⁹ is H or d-dalkyl;

and wherein R²⁰ is hydrogen, d-dalkyl, d-dalkenyl, d-dalkynyl, d-dcycloalkyl, C₃- dcycloalkyl-CH₂, d-dhaloalkyl, d-dalkoxyalkyl, d-dhaloalkoxyalkyl, d-dalkoxy-d-dalkyl, d- dalkoxy, d-dalkylcarbonyl, d-dhaloalkylcarbonyl, phenyl-CH₂-alkyl- or phenyl-CH₂- wherein the phenyl moiety is substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy, furanyl or furanyl substituted by one to three groups

independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy, thietanyl, oxetanyl, 1-oxo-thietanyl, or 1 ,1-dioxo-thietanyl.

More preferably R² is d-dalkyl or d-dalkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-dalkoxy, d-dalkylthio, d-d alkylsulfinyl and d-dalkylsulfonyl, C₃-C₈cycloalkyl or C₃-C₈cycloalkyl substituted by one to three R ³, C₃- C₈cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₈cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to three groups R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)-, aryl or aryl substituted by one to five R ⁴, heterocyclyl, d- C₄alkylaminocarbonyl-CH₂-, d-dhaloalkylaminocarbonyl-CH₂-, d-C₆alkylaminocarbonyl-, d-dalkyl-O- N=CH-, or d-dhaloalkyl-0-N=CH-;

wherein heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0₂ as ring atoms, wherein the ring is optionally substituted by one or two methyl;

or heterocycyl is a 5- or 6-membered saturated heterocyclic ring containing N(R²⁰) and optionally an O atom as ring atoms, wherein one carbon ring atom is substituted by oxo;

or heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, wehrein the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy; _„

-10- wherein each R ³ is independently halogen, cyano, Ci-C₄alkyl, or two R ³ are together R ⁹-0-N=; wherein each R ⁴ is independently halogen, cyano, nitro, Ci-C₄alkyl, Ci-C₄haloalkyl, d-C₄alkoxy, or Ci-C₄haloalkoxy;

wherein R ⁷ is hydrogen;

wherein R ⁸ is hydrogen or methyl;

wherein R ⁹ is hydrogen or Ci-C₄alkyl;

and wherein R²⁰ is hydrogen, Ci-C₄alkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, C₃-C₆cycloalkyl, C₃- C₆cycloalkyl-CH₂-, Ci-C₄haloalkyl or Ci-C₄alkoxy.

In another group of compounds R² is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C₄alkoxy, d-

C₄alkylthio, Ci-C₄ alkylsulfinyl and Ci-C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by substituted by one to three R ³, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by substituted by one to three R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- or heterocyclyl-C(R ⁷)(R¹⁸)- wherein the heterocyclyl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴, Ci-C₄alkylaminocarbonyl-CH₂-, d-dhaloalkylaminocarbonyl- CH₂-, d-Cealkylaminocarbonyl-, d-C₄alkyl-0-N=CH-, or d-dhaloalkyl-0-N=CH-;

wherein heterocyclyl is pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, thiolanyl, thiolanyl 1 -oxide, thiolanyl 1 ,1 -dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 ,1-dioxo-thietanyl, pyrrolidinyl, tetrahydrofuranyl, [1 ,3]dioxolanyl, piperidinyl, piperazinyl, [1 ,4]dioxanyl, morpholinyl, 2,3- dihydro-benzofuranyl, benzo[1 ,3]dioxolanyl, 2,3-dihydro-benzo[1 ,4]dioxinyl, 3-oxo-isoxazolidinyl, 2,5- dioxo-1-pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 4-oxo-1 ,3-oxazinanyl, tetrahydropyranyl, or 1-oxa-3,4-diazolyl, and wherein an N atom in heterocycyl is optionally substituted by R²⁰;

wherein aryl is phenyl;

wherein R ⁷ is hydrogen;

wherein R ⁸ is hydrogen or methyl;

wherein R ⁹ is hydrogen or d-dalkyl;

and wherein R²⁰ is hydrogen, d-dalkyl, d-dalkenyl, C₂-C₄alkynyl, d-dcycloalkyl, d- dcycloalkyl-CH₂-, d-dhaloalkyl or d-dalkoxy.

More preferably R² is d-dalkyl or d-dalkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-dalkoxy, d-dalkylthio, d-d alkylsulfinyl and d-dalkylsulfonyl, d-dcycloalkyl or d-dcycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or d-dcycloalkyl- C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)-, aryl or aryl substituted by one to five R ⁴, heterocyclyl, d- C₄alkylaminocarbonyl-CH₂-, Ci-C₄haloalkylaminocarbonyl-CH₂-, Ci-C₆alkylaminocarbonyl-, Ci-C₄alkyl-0- N=CH-, or C₁-C₄haloalkyl-0-N=CH-;

wherein heterocyclyl is selected from tetrahydrofuranyl, thiolanyl, thiolanyl 1-oxide, thiolanyl 1 ,1- dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 ,1 ,-dioxothietanyl each optionally substituted by methyl; or heterocyclyl is 3-oxo-isoxazolidinyl, 2,5-dioxo-1-pyrrolidinyl, 2-oxo-1-pyrrolidinyl, wherein each is substituted on the nitrogen atom by Ci-C₄alkyl, C₃-C₆cycloalkyl, C3-C₆cycloalkyl-CH₂ or Ci-C₄haloalkyl; or heterocycyl is 4-oxo-1 ,3-oxazinanyl, piperidinyl, tetrahydropyranyl, thiazolinyl, pyrimidyl, 1-oxa- 3,4-diazolyl, pyridyl, and thiazolyl, each optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy;

wherein aryl is phenyl;

wherein R ⁷ is hydrogen;

and wherein R ⁸ is hydrogen or methyl.

More preferably R² is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from methoxy, methylthio, methylsulfinyl and methysulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl- C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, pyridyl or pyridyl substituted by one to four R ⁴, Ci-C₄alkylaminocarbonyl-CH₂-, C-r C₄haloalkylaminocarbonyl-CH₂-, Ci-C₄alkylaminocarbonyl,

or Ci-C₄haloalkyl-0- N=CH-;

wherein each R ⁴ is independently halogen, cyano, methyl, halomethyl, methoxy or halomethoxy;

wherein R ⁷ is hydrogen;

wherein R ⁸ is hydrogen or methyl;

wherein R²⁰ is Ci-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₆cycloalkyl-CH₂-, or Ci-C₄haloalkyl;

wherein q is 0, 1 or 2.

Most preferably R² is C₄-C₅cycloalkyl, pyridyl-CH₂-, Ci-C₄alkylaminocarbonyl-CH₂-, d- C₄haloalkylaminocarbonyl-CH₂-,;

Preferably R³ is trifluoromethyl, difluoromethyl or chlorodifluoromethyl, most preferably trifluoro- methyl.

Preferably R⁴ is aryl or aryl substituted by one to five R ⁵, more preferably aryl substituted by one to three R ⁵, more preferably phenyl substituted by one to three R ⁵.

In one group of compounds R⁴ is group (C)

wherein X² is C-X⁶ or nitrogen (preferably C-X⁶); X¹, X³ and X⁶ are independently hydrogen, halogen or trihalomethyl, e.g. wherein at least two of X¹, X³ and X⁶ are not hydrogen. Preferably R⁴ is 3,5-dichlorophenyl, 3-chloro-4-fluorophenyl, 3-fluoro-4-chlorophenyl, 3,4- dichlorophenyl, 3-chloro-4-bromophenyl, 3,5-dichloro-4-fluorophenyl, 3,4,5-trichlorophenyl, 3,5-dichloro-4- iodophenyl, 3,4,5-trifluorophenyl, 3-chloro-5-bromophenyl, 3-chloro-5-fluorophenyl, 3-chloro-5- (trifluoromethyl)phenyl, 3,4-dichloro-5-(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 4-chloro-3,5- bis(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 2,6-dichloro-4-pyridyl, 2,6-bis(trifluoromethyl)-4- pyridyl, 2-chloro-4-pyridyl-, 2-trifluoromethyl-4-pyridyl, more preferably 3,5-dichloro-phenyl, 3-chloro-5- bromophenyl, 3-chloro-5-(trifluoromethyl)phenyl, 3,5-dichloro-4-fluorophenyl, 3,4,5-trichlorophenyl, 3,5- bis(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 2,6-dichloro-4-pyridyl, 2,6-bis(trifluoromethyl)-4- pyridyl, 3,5-dichloro-4-bromophenyl, 3-bromo-5-(trifluoromethyl)phenyl, 3,5-dibromophenyl, or 3,4- dichlorophenyl, 2-chloro-4-pyridyl-, 2-trifluoromethyl-4-pyridyl, even more preferably 3,5-dichloro-phenyl, 3,5-dichloro-4-fluorophenyl, 3,4,5-trichlorophenyl, 3-(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, most preferably 3,5-dichloro-phenyl, 3,5-dichloro-4-fluorophenyl, or 3,4,5-trichlorophenyl-.ln one group of compounds R⁴ is 3,5-dichloro-phenyl. In one group of compounds R⁴ is 3,5-dichloro-4-fluorophenyl-. In one group of compounds R⁴ is 3,4,5-trichlorophenyl-. In one group of compounds R⁴ is 3,5- bis(trifluoromethyl)phenyl.

Preferably each R⁵ is independently hydrogen, halogen, cyano, nitro, NH₂, Ci-C₈alkyl, C-i-C₈halo- alkyl, C₃-C₅cycloalkyl, C₃-C₅halocycloalkyl, Ci-C₈alkenyl, Ci-C₈haloalkenyl, d-C₈alkoxy, or C-i-C₈halo- alkoxy, preferably halogen, cyano, nitro, NH₂, Ci-C₂alkyl, Ci-C₂haloalkyl, C₃-C₅cycloalkyl, C₃- C₅halocycloalkyl, Ci-C₂alkoxy, Ci-C₂haloalkoxy, more preferably hydrogen, chloro, bromo, fluoro, trifluoromethyl, methyl, ethyl, methoxy, nitro, trifluoromethoxy, cyano, cyclopropyl, even more preferably hydrogen, chloro, bromo, fluoro, methyl, ethyl or trifluoromethyl, even more preferably hydrogen, chloro, bromo, fluoro, methyl or trifluoromethyl, more preferably chloro, bromo or methyl, most preferably methyl. In one group of compounds R⁵ is chloro. In one group of compounds R⁵ is bromo. In one group of compounds R⁵ is methyl. In one group of compounds R⁵ is halogen.

Preferably at least one of R^6a and R^6b is hydrogen or Ci-C₈alkyl, and the other is selected from hydrogen, halogen, cyano, Ci-C₈alkyl, Ci-C₈haloalkyl and C₃-C₈cycloalkyl, or R^6a and R^6b together from a 3- to 6-membered carbocyclic ring, more preferably at least one of R^6a and R^6b is hydrogen or methyl and the other is hydrogen, methyl, ethyl or cyclopropyl or R^6a and R^6b together form a 3- to 4-membered carbocyclic ring, most preferably one of R^6a and R^6b is hydrogen and the other is hydrogen or methyl.

Preferably R⁷ is hydrogen, methyl, ethyl, methylcarbonyl, or methoxycarbonyl, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.

Preferably R⁸ is Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃- docycloalkyl substituted by one to five R ³, C₃-C₁₀cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₁₀cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- or heterocyclyl-C(R ⁷)(R¹⁸)- wherein the heterocyclyl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, or heterocyclyl or heterocyclyl substituted by one to five R ⁴;

wherein heterocyclyl is a 4- to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, SO, S0₂, N, and N(R¹⁴) as ring atoms;

wherein aryl is phenyl; and wherein R ⁷ and R ⁸ are independently selected from hydrogen, cyano, halogen, Ci-C₄alkyl, Ci-C₄haloalkyl, d-C₄alkoxy, Ci-C₄haloalkoxy and C₃-C₆cycloalkyl.

More preferably R⁸ is Ci-C₆alkyl or Ci-C₆alkyl substituted by one to five R ², C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to five R ³, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or d-docycloalkyl- C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

wherein heterocyclyl is a 4- to 6-membered saturated heterocyclic ring containing one or two heteroatoms independently selected from O, S, SO, S0₂ and N(R²⁰) as ring atoms, wherein one or two carbon ring atoms are optionally substituted by oxo, and wherein the ring is optionally substituted by one or two R ⁴;

wherein R ⁷ is hydrogen;

and wherein R ⁸ is independently hydrogen, cyano, halogen, Ci-C₄alkyl, Ci-C₄haloalkyl, d- C₄alkoxy, Ci-C₄haloalkoxy or C₃-C₆cycloalkyl;

and wherein R²⁰ is hydrogen or R ⁴.

More preferably R⁸ is Ci-C₆alkyl or Ci-C₆alkyl substituted by one to five R ², C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to five R ³, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

wherein heterocyclyl is a 4- to 6-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, S0₂ and N(R²⁰) as ring atoms, wherein the ring is optionally substituted by one or two methyl;

or heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, wehrein the ring is optionally substituted by one to three groups independently selected from halogen, cyano, Ci-C₄alkyl, Ci-C₄haloalkyl, Ci-C₄alkoxy, Ci-C₄haloalkoxy;

wherein each R ² is independently halogen, d-C₈alkoxy, Ci-C₈haloalkoxy-mercapto, d- dalkylthio, d-dhaloalkylthio, d-dalkylsulfinyl, d-dhaloalkylsulfinyl, d-dalkylsulfonyl, or d- dhaloalkylsulfonyl;

wherein each R ³ is independently halogen, cyano, or d-dalkyl;

wherein each R ⁴ is independently halogen, cyano, nitro, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, or d-dhaloalkoxy;

wherein R ⁷ is hydrogen;

wherein R ⁸ is independently hydrogen, cyano, halogen, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy or C₃-C₆cycloalkyl;

wherein R ⁹ is hydrogen or d-dalkyl;

and wherein R²⁰ is hydrogen or R ⁴. More preferably R is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-C₄alkoxy, Ci-C₄alkylthio, Ci-C₄ alkylsulfinyl and Ci-C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl- C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

wherein heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0₂ as ring atoms, and wherein the ring is optionally substituted by one or two methyl;

or heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, wehrein the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy;

wherein each R ⁴ is independently halogen, cyano, nitro, Ci-C₄alkyl, Ci-C₄haloalkyl, Ci-C₄alkoxy, or Ci-C₄haloalkoxy;

wherein R ⁷ is hydrogen;

and wherein R ⁸ is hydrogen or methyl.

In another group of compounds R⁸ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C₄alkoxy, d- C₄alkylthio, Ci-C₄ alkylsulfinyl and Ci-C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃- C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- or heterocyclyl-C(R ⁷)(R¹⁸)- wherein the heterocyclyl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴;

wherein heterocyclyl is pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, benzothiazolyl, thiolanyl, thiolanyl 1 -oxide, thiolanyl 1 ,1 -dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 ,1-dioxo-thietanyl, pyrrolidinyl, tetrahydrofuranyl, [1 ,3]dioxolanyl, piperidinyl, piperazinyl, [1 ,4]dioxanyl, morpholinyl, 2,3- dihydro-benzofuranyl, benzo[1 ,3]dioxolanyl, 2,3-dihydro-benzo[1 ,4]dioxinyl, 3-oxo-isoxazolidinyl, 2,5- dioxo-1-pyrrolidinyl, 2-oxo-1-pyrrolidinyl, 4-oxo-1 ,3-oxazinanyl, tetrahydropyranyl, or 1-oxa-3,4-diazolyl; wherein aryl is phenyl;

wherein R ⁷ is hydrogen;

and wherein R ⁸ is hydrogen or methyl.

More preferably R⁸ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from methoxy, methylthio, methylsulfinyl and methysulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently _ _.

-15- selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl- C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl- C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

wherein heterocyclyl is tetrahydrofuranyl, thiolanyl, thiolanyl 1-oxide, thiolanyl 1 , 1-dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 , 1 ,-dioxothietanyl each optionally substituted by methyl;

or heterocycyl is piperidinyl, tetrahydropyranyl, pyridyl, or thiazolyl, each optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy;

wherein aryl is phenyl;

wherein R ⁷ is hydrogen;

and wherein R ⁸ is hydrogen or methyl.

Most preferably R⁸ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-C₄alkoxy, Ci-C₄alkylthio, Ci-C₄ alkylsulfinyl and Ci-C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl- C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, pyridyl or pyridyl substituted by one to four R ⁴;

wherein each R ⁴ is independently halogen, cyano methyl, halomethyl, methoxy or halomethoxy; wherein R ⁷ is hydrogen;

wherein R ⁸ is hydrogen or methyl;

wherein q is 0, 1 or 2.

Preferably R⁹ is hydrogen, methyl, ethyl, methylcarbonyl, or methoxycarbonyl, more preferably hydrogen, methyl or ethyl, most preferably hydrogen.

Preferably R ⁰ is Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃- docycloalkyl substituted by one to five R ³, C₃-C₁₀cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₁₀cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- or heterocyclyl-C(R ⁷)(R¹⁸)- wherein the heterocyclyl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, or heterocyclyl or heterocyclyl substituted by one to five R ⁴;

wherein aryl is phenyl;

and wherein R ⁷ and R ⁸ are independently selected from hydrogen, cyano, halogen, Ci-C₄alkyl,

Ci-C₄haloalkyl, Ci-C₄alkoxy, Ci-C₄haloalkoxy and C₃-C₆cycloalkyl.

More preferably R ⁰ is Ci-C₆alkyl or Ci-C₆alkyl substituted by one to five R ², C₃-C₆cycloalkyl or

C₃-C₆cycloalkyl substituted by one to five R ³, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-Ci₀cycloalkyl-

C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl; wherein heterocyclyl is a 4- to 6-membered saturated heterocyclic ring containing one or two heteroatoms independently selected from O, S, SO, S0₂ and N(R¹⁴) as ring atoms, wherein one or two carbon ring atoms are optionally substituted by oxo, and wherein the ring is optionally substituted by one or two R ⁴;

wherein R ⁷ is hydrogen;

and wherein R ⁸ is independently hydrogen, cyano, halogen, Ci-C₄alkyl, Ci-C₄haloalkyl, d- C₄alkoxy, Ci-C₄haloalkoxy or C₃-C₆cycloalkyl.

More preferably R ⁰ is Ci-C₆alkyl or Ci-C₆alkyl substituted by one to five R ², C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to five R ³, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

wherein heterocyclyl is a 4 or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0₂ as ring atoms, wherein the ring is optionally substituted by one or two methyl;

wherein each R ² is independently halogen, d-C₈alkoxy, Ci-C₈haloalkoxy-mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, or d- C₈haloalkylsulfonyl;

wherein each R ³ is independently halogen, cyano, or d-dalkyl;

wherein R ⁷ is hydrogen;

and wherein R ⁹ is hydrogen or d-dalkyl.

More preferably R ⁰ is d-dalkyl or d-dalkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-dalkoxy, d-dalkylthio, d-d alkylsulfinyl and d-dalkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl- C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

wherein heterocyclyl is a 4- or 5-membered saturated heterocyclic ring containing one heteroatom independently selected from O, S, SO, and S0₂ as ring atoms, and wherein the ring is optionally substituted by one or two methyl; or heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, wehrein the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy;

wherein each R ⁴ is independently halogen, cyano, nitro, Ci-C₄alkyl, Ci-C₄haloalkyl, d-C₄alkoxy, or Ci-C₄haloalkoxy;

wherein R ⁷ is hydrogen;

and wherein R ⁸ is hydrogen or methyl.

In another group of compounds R ⁰ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C₄alkoxy, d- C₄alkylthio, Ci-C₄ alkylsulfinyl and Ci-C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃- C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- or heterocyclyl-C(R ⁷)(R¹⁸)- wherein the heterocyclyl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴;

wherein R ⁷ is hydrogen;

and wherein R ⁸ is hydrogen or methyl.

More preferably R ⁰ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from methoxy, methylthio, methylsulfinyl and methysulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl- C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl- C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

wherein heterocyclyl is tetrahydrofuranyl, thiolanyl, thiolanyl 1-oxide, thiolanyl 1 ,1-dioxide, oxetanyl, thietanyl, 1-oxo-thietanyl, 1 ,1 ,-dioxothietanyl each optionally substituted by methyl;

wherein aryl is phenyl; _„

-18- wherein R ⁷ is hydrogen;

and wherein R ⁸ is hydrogen or methyl.

Most preferably R ⁰ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-C₄alkoxy, Ci-C₄alkylthio, Ci-C₄ alkylsulfinyl and Ci-C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl- C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, pyridyl or pyridyl substituted by one to four R ⁴, or R ⁰ is selected from groups A1-A12 (preferably A2 or A8);

wherein R ⁸ is hydrogen or methyl;

wherein q is 0, 1 or 2.

Preferably each R is independently hydrogen, halogen, cyano, Ci-C₄alkyl, Ci-C₄haloalkyl, d-

C₄alkoxy, or Ci-C₄haloalkoxy, more preferably hydrogen, bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably hydrogen, bromo, chloro, fluoro, cyano or methyl, most preferably hydrogen.

Preferably each R ² is independently halogen, cyano, nitro, hydroxy, d-C₈alkoxy, d- dhaloalkoxy, Ci-C₈alkylcarbonyl, Ci-C₈alkoxycarbonyl, mercapto, Ci-Csalkylthio, Ci-Cshaloalkylthio, Ci- C₈alkylsulfinyl, d-C₈haloalkylsulfinyl, d-C₈alkylsulfonyl, or d-C₈haloalkylsulfonyl, more preferably halogen, cyano, nitro, hydroxy, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, Ci-C₈alkylthio, or Ci- Cshaloalkylthio, more preferably halogen, cyano, d-C₈alkoxy, d-C₈haloalkoxy, mercapto, Ci-C₈alkylthio, or Ci-C₈haloalkylthio, even more preferably halogen, Ci-C₄alkoxy, Ci-C₄alkylthio, Ci-C₄ alkylsulfinyl or Ci-C₄alkylsulfonyl, most preferably halogen, methoxy, methylthio, methylsulfinyl or methysulfonyl.

Preferably each R ³ is independently halogen, cyano, or Ci-C₄alkyl, or two R ³ are together R ⁹- 0-N=, more preferably halogen or methyl, even more preferably chloro, fluoro or methyl, most preferably fluoro or methyl.

Preferably each R ⁴ is independently halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, C₂- C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, hydroxy, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, Ci-C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, Ci-C₈haloalkylsulfonyl, Ci-C₈alkylcarbonyl, Ci-C₈alkoxycarbonyl, aryl or aryl substituted by one to five R ⁶, or heterocyclyl or heterocyclyl substituted by one to five R ⁶, more preferably halogen, cyano, nitro, Ci-C₄alkyl, Ci-C₄haloalkyl, Ci-C₄alkoxy, or Ci-C₄haloalkoxy, even more preferably halogen, cyano, methyl, halomethyl, methoxy, or halomethoxy; most preferably bromo, chloro, fluoro, methyl, halomethyl, methoxy or halomethoxy.

Preferably each R ⁵ is independently halogen, Ci-C₈alkyl, Ci-C₈haloalkyl, Ci-C₈alkoxy, Ci- C₈haloalkoxy, d-C₈alkylthio, or Ci-C₈haloalkylthio, more preferably bromo, chloro, fluoro, trifluoromethyl, methoxy, or methylthio, most preferably trifluoromethyl, fluoro or chloro. Preferably each R ⁶ is independently bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, or trifluoromethoxy, more preferably bromo, chloro, fluoro, nitro, or methyl, most preferably chloro, fluoro, or methyl.

Preferably n is 1 ;

Preferably p is 0, 1 , or 2, preferably 0 or 1 , most preferably 0;

In one embodiment (E1 ) n is 1 and p is 0.

In one embodiment (E2) P is P1 .

In another Embodiment (E3) P is P2.

In another embodiment (E4) P and A¹ = C-R⁵ together are P3 or P and A¹ = C-R^5b together are P3 respectively.

In another embodiment (E6) A¹ is C-R⁵, A² is CH, A³ is CH and A⁴ is CH

In another embodiment (E6) A¹ is CH, A² is CH, A³ is CH and A⁴ is CH.

In another embodiment (E7) A¹ is CH, A² is CH, A³ is CH and A⁴ is CH and P is P1.

In another embodiment (E8) A¹ is CH, A² is CH, A³ is CH and A⁴ is CH and P is P2.

In another embodiment (E9) A² is CH, A³ is CH and A⁴ is CH and P and A¹ = C-R⁵ together are

P3 or P and A¹ = C-R^5b together are P3 respectively.

In another embodiment (E1 1 ) A¹ is C-R⁵, A² is C-R⁵, A³ is CH and A⁴ is CH and both R⁵ togther form a -CH=CH-CH=CH- bridge.

In another embodiment (E12) A¹ is C-R⁵, A² is C-R⁵, A² is CH and A⁴ is CH and both R⁵ togther form a -CH=CH-CH=CH- bridge and P is P1.

In another embodiment (E13) A³ is C-R⁵, A⁴ is C-R⁵, A³ is CH and A⁴ is CH and both R⁵ togther form a -CH=CH-CH=CH- bridge and P is P2.

In another embodiment (E14) A³ is C-R⁵, A⁴ is C-R⁵, A² is CH and A¹ is C-R⁵ and both R⁵ togther form a -CH=CH-CH=CH- bridge and P and A¹ = C-R⁵ together are P3.

G , G², G³ and G⁴ are oxygen;

A¹ , A², and A³ are C-H;

R , R⁷ and R⁹ are hydrogen;

R² is Ci-C₆alkyl or d-C₆alkyl substituted by one to five R ², C₃-C₈cycloalkyl or C₃-C₈cycloalkyl substituted by one to five R ³, C₃-C₈cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₈cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, heterocyclyl, Ci-C₆alkylaminocarbonyl-CH₂-, Ci-C₆haloalkylaminocarbonyl-CH₂-, C₃-C₈cycloalkyl- aminocarbonyl-CH₂-, aryl-CH₂-aminocarbonyl-CH₂- or aryl-CH₂-aminocarbonyl-CH₂- wherein the aryl is substituted by one to five R ⁴, Ci-C₆alkylaminocarbonyl-, C₃-C₆cycloalkylaminocarbonyl-, d-C₄alkyl-0- N=CH-, or C₁-C₄haloalkyl-0-N=CH-;

or heterocyclyl is a 5 or 6-membered saturated or partially saturated heterocyclic ring containing one or two heteroatoms selected from, N(R²⁰), N, S and O as ring atoms, wherein one or two carbon ring atoms are optionally substituted by oxo; „„

-20- or heterocycyl is a 6-membered heteroaryl ring containing one to three heteroatoms selected from O, N and S as ring atoms, wehrein the ring is optionally substituted by one to three groups independently selected from halogen, cyano, Ci-C₄alkyl, Ci-C₄haloalkyl, d-C₄alkoxy, Ci-C₄haloalkoxy and C₃-C₆cycloalkyl;

R³ is trifluoromethyl or chlorodifluoromethyl;

R⁴ is group (C)

wherein X² is C-X⁶ or nitrogen (preferably C-X⁶); X¹, X³ and X⁶ are independently hydrogen, halogen or trihalomethyl, wherein at least one of X¹, X³ and X⁶ is not hydrogen;

R⁵ is hydrogen, chloro, bromo, fluoro, methyl, ethyl or trifluoromethyl;

at least one of R^6a and R^6b is hydrogen or methyl and the other is hydrogen, methyl, ethyl or cyclopropyl or R^6a and R^6b together form a 3- to 4-membered carbocyclic ring,

R⁸ is Ci-C₆alkyl or d-C₆alkyl substituted by one to five R ², C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to five R ³, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

R ⁰ is Ci-C₆alkyl or d-C₆alkyl substituted by one to five R ², C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to five R ³, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to five R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

herein each R ² is independently halogen, d-C₈alkoxy, d-C₈haloalkoxy-mercapto, d-

C₈alkylthio, d-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, or d- C₈haloalkylsulfonyl; _

-21- wherein each R ³ is independently halogen, cyano, Ci-C₄alkyl, or two R ³ are together R ⁹-0-N=; wherein each R ⁴ is independently halogen, cyano, nitro, Ci-C₄alkyl, Ci-C₄haloalkyl, d-C₄alkoxy, or Ci-C₄haloalkoxy;

wherein R ⁷ is hydrogen or Ci-C₄alkyl;

wherein R ⁸ is independently hydrogen, cyano, halogen, Ci-C₄alkyl, Ci-C₄haloalkyl, Ci-C₄alkoxy,

Ci-C₄haloalkoxy or C₃-C₆cycloalkyl;

or R ⁷ and R ⁸ together form a three to six membered carbocycle;

wherein R ⁹ is H or Ci-C₄alkyl;

and wherein R²⁰ is hydrogen, Ci-C₄alkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, C₃-C₆cycloalkyl, C₃- C₆cycloalkyl-CH₂, Ci-C₄haloalkyl, Ci-C₄alkoxyalkyl, Ci-C₄haloalkoxyalkyl, Ci-C₄alkoxy-Ci-C₄alkyl, d- C₄alkoxy, Ci-C₄alkylcarbonyl, Ci-C₄haloalkylcarbonyl, phenyl-CH₂-alkyl- or phenyl-CH₂- wherein the phenyl moiety is substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy, furanyl or furanyl substituted by one to three groups

each Z is independently hydrogen, halogen, cyano, methyl, halomethyl, methoxy or halomethoxy; and n is 1 or 2, p is 0.

In another embodiment (E17):

P is selected from P1 and P2, or P and A¹ = C-R⁵ together are P3;

G , G² and G³ are oxygen;

A , A², A³and A⁴ are C-H;

R , R⁷ and R⁹ are hydrogen;

R² is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C₄alkoxy, Ci-C₄alkylthio, Ci-C₄ alkylsulfinyl and d- C₄alkylsulfonyl, C₃-C₈cycloalkyl or C₃-C₈cycloalkyl substituted by one to three R ³, C₃-C₈cycloalkyl- C(R ⁷)(R¹⁸)- or C₃-C₈cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyl is substituted by one to three groups R ³, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl- C(R ⁷)(R¹⁸)-, aryl or aryl substituted by one to five R ⁴, heterocyclyl, Ci-C₄alkylaminocarbonyl-CH₂-, d- C₄haloalkylaminocarbonyl-CH₂-, Ci-C₆alkylaminocarbonyl-,

or d-dhaloalkyl-O- N=CH-;

R³ is trifluoromethyl or chlorodifluoromethyl;

R⁴ is group (C)

wherein X² is C-X⁶ or nitrogen (preferably C-X⁶); X¹ , X³ and X⁶ are independently hydrogen, halogen or trihalomethyl, wherein at least one of X¹ , X³ and X⁶ is not hydrogen;

R⁵ is hydrogen, chloro, bromo, fluoro, or methyl;

R^6a and R^6b are independently hydrogen or methyl;

R⁸ is R⁸ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from d-C₄alkoxy, Ci-C₄alkylthio, Ci-C₄ alkylsulfinyl and d- C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl- C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl- C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

or heterocycyl is a 6-membered heteroaryl ring containing one or two N atoms as ring atoms, wehrein the ring is optionally substituted by one to three groups independently selected from halogen, cyano, methyl, halomethyl, methoxy and halomethoxy.

R ⁰ is R⁸ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C₄alkoxy, Ci-C₄alkylthio, Ci-C₄ alkylsulfinyl and d- C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl- C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl- C(R ⁷)(R¹⁸)- , aryl or aryl substituted by one to five R ⁴, or heterocyclyl;

wherein each R ³ is independently halogen, cyano, Ci-C₄alkyl, or two R ³ are together R ⁹-0-N=; wherein each R ⁴ is independently halogen, cyano, nitro, Ci-C₄alkyl, Ci-C₄haloalkyl, Ci-C₄alkoxy, or Ci-C₄haloalkoxy;

wherein R ⁷ is hydrogen;

wherein R ⁸ is hydrogen or methyl;

wherein R ⁹ is hydrogen or Ci-C₄alkyl; and wherein R is hydrogen, Ci-C₄alkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, C₃-C₆cycloalkyl, C₃- C₆cycloalkyl-CH₂-, Ci-C₄haloalkyl or Ci-C₄alkoxy.

each Z is independently hydrogen, halogen, cyano, methyl, halomethyl, methoxy or halomethoxy; and n is 1 , p is 0; k is 0 or 1.

In another embodiment (E18):

P is selected from P1 and P2, or P and R⁵ together are P3, or H2 or H6;

G , G² and G³ are oxygen;

A¹, A², A³ and A⁴ are C-H;

R , R⁷ and R⁹ are hydrogen;

R² is -|-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from methoxy, methylthio, methylsulfinyl and methysulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl-C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, pyridyl or pyridyl substituted by one to four R ⁴, Ci-C₄alkylaminocarbonyl-CH₂-, C-r

C₄haloalkylaminocarbonyl-CH₂-, Ci-C₄alkylaminocarbonyl,

or Ci-C₄haloalkyl-0- N=CH-, or R² is selected from groups A1-A12 and B1-B6 (preferably A2, A8 and B1 )

R³ is trifluoromethyl or chlorodifluoromethyl;

R⁴ is group (C)

R⁵ is hydrogen, chloro, bromo, fluoro, or methyl;

R^6a and R^6b are independently hydrogen or methyl;

R⁸ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C₄alkoxy, Ci-C₄alkylthio, Ci-C₄ alkylsulfinyl and d-

C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl-

C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, pyridyl or pyridyl substituted by one to four R ⁴;

R ⁰ is Ci-C₄alkyl or Ci-C₄alkyl wherein a terminal carbon atom is substituted by one to three halogen or substituted by one group selected from Ci-C₄alkoxy, Ci-C₄alkylthio, Ci-C₄ alkylsulfinyl and d- C₄alkylsulfonyl, C₃-C₆cycloalkyl or C₃-C₆cycloalkyl substituted by one to three groups independently selected from halogen and methyl, C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- or C₃-C₆cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to three groups independently selected from halogen and methyl, aryl- „

-24-

each R ⁴ is independently halogen, cyano, methyl, halomethyl, methoxy or halomethoxy;

R ⁷ is hydrogen;

R ⁸ is hydrogen or methyl;

R²⁰ is d-C₄alkyl, C₃-C₆cycloalkyl, C₃-C₆cycloalkyl-CH₂-, or C₁-C₄haloalkyl;

each Z is independently hydrogen, halogen, cyano, methyl, halomethyl, methoxy or halomethoxy; and n is 1 , p is 0; q is 0, 1 or 2; k is 0 or 1.

In one embodiment (E23) P is P and R , R², G , R³, R⁴, R⁵, A¹, A², A³ and A⁴ are as defined in embodiment E17.

In another Embodiment (E24) P is P2 and R⁵, R^6a, R^6b, R⁷, R⁸, R³, R⁴, R⁵, A¹, A², A³ and A⁴ are as defined in embodiment E17.

In another embodiment (E25) P and A¹ = C-R⁵ together are P3 and R⁹, R ⁰, R , p, n, R³, R⁴, R⁵, A¹, A², A³ and A⁴ A³ are as defined in embodiment E17.

In one embodiment (E27) P is P and R¹, R², G , R³, R⁴, R⁵, A¹, A², A³ and A⁴ are as defined in embodiment E18.

In another Embodiment (E28) P is P2 and R⁵, R^6a, R^6b, R⁷, R⁸, R³, R⁴, R⁵, A¹, A², A³ and A⁴ are as defined in embodiment E18.

In another embodiment (E29) P and A¹ = C-R⁵ together are P3 and R⁹, R ⁰, R , p, n, R³, R⁴, R⁵, A¹, A², A³ and A⁴ are as defined in embodiment E18.

In a preferred embodiment (E30) according to the present invention the embodiments E1 to E29 A¹ is C-R^5b;

A², A³ and A⁴ are independently of one another C-H, C-R^5a or nitrogen;

each R^5a is independently hydrogen, halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, d- C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₃-Ci₀cycloalkyl, Ci-C₈alkoxy, d-

C₈haloalkoxy, Ci-C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, d-

C₈alkylsulfonyl, or Ci-C₈haloalkylsulfonyl, or two R⁵ on adjacent carbon atoms together form a -CH=CH-

CH=CH- bridge or a -N=CH-CH=CH- bridge

each R^5b is independently halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, Ci-C₈alkenyl, C₂- Cshaloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₃-Ci₀cycloalkyl, Ci-C₈alkoxy, Ci-C₈haloalkoxy, d-

C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, or d-

C₈haloalkylsulfonyl, or two R⁵ on adjacent carbon atoms together form a -CH=CH-CH=CH- bridge or a -

N=CH-CH=CH- bridge

In one further preferred embodiment the invention provides compounds of formula I

wherein P is selected from P1 and P2, or P and A¹ = C-R⁵ together are P3

P1 P2 P3

A¹ is C-R⁵ and A², A³,and A⁴ each C-H;

G , G² and G³ are oxygen;

R is hydrogen;

R² is Ci-C₄alkyl or d-C₄haloalkyl;

R³ is C₁-C₄haloalkyl

R⁴ is phenyl or phenyl substituted by one to five halogene atoms;

R⁵ is hydrogen, halogen, cyano, d-C₄alkyl, Ci-C₄haloalkyl;

R^6a and R^6b are each independently hydrogen, halogen, cyano, Ci-C₄alkyl, Ci-C₄haloalkyl;

R⁷ is hydrogen, Ci-C₄alkyl, preferably hydrogen

R⁸ is Ci-C₄alkyl, Ci-C₄haloalkyl, Ci-C₄alkylthioCi-C₄alkyl or C₃-Ci₀cycloalkyl;

R⁹ is hydrogen, d-C₈alkyl;

R ⁰ is Ci-C₄alkyl, Ci-C₄haloalkyl, or C₃-Ci₀cycloalkyl;

R is hydrogen;

n is 0; Preferably

A¹ is C-R⁵ and A², A³,and A⁴ each C-H;

G , G² and G³ are oxygen;

R is hydrogen;

R² is ethyl, 2,2,2-trifluoroethyl- or cyclopropyl;

R³ is trifluoromethyl

R⁴ is phenyl or phenyl substituted by one to three halogene atoms preferably by two halogen atoms; R⁵ is hydrogen, halogen, methyl, ethyl, preferably halogen or methyl;

R^6a and R^6b are each independently hydrogen, methyl, ethyl, preferably hydrogen or methyl;

R⁷ is hydrogen;

R⁸ is cyclopropyl, isopropyl, ethyl, chloromethyl, methylthiomethyl or 2,2,2-trifluoroethyl-;

R⁹ is hydrogen;

R ⁰ is methyl, cyclopropyl or isopropyl;

R is hydrogen;

n is 0. „„

-26-

More preferably

A¹ , A², A³,and A⁴ are independently of each other C-H, C-R⁵, or nitrogen;

A¹ is C-R⁵ and A², A³,and A⁴ each C-H;

G , G² and G³ are oxygen;

R is hydrogen;

R² is ethyl, 2,2,2-trifluoroethyl- or cyclopropyl;

R³ is trifluoromethyl

R⁴ is phenyl or phenyl substituted by one to three halogene atoms preferably by two halogen atoms; R⁵ is preferably halogen or methyl;

R^6a and R^6b are each hydrogen or methyl;

R⁷ is hydrogen;

R⁹ is hydrogen;

R¹⁰ is methyl, cyclopropyl or isopropyl;

R is hydrogen;

n is 0.

In one even further preferred embodiment the invention provides compounds of the following

Wherein the substituents have the meaning as given above

Wherein the substituents have the meaning as given above

Certain intermediates are novel and are also included as further aspects of the invention.

In a further aspect the invention provides compounds of formula lnt-1

wherein A¹ , A², A³, A⁴, R³ and R⁴ are as defined for the compound of formula I or a salt or N-oxide thereof. Preferred definitions of A¹ , A², A³, A⁴, R³ and R⁴ are as defined for compounds of formula I.

In a further aspect the invention provides compounds of formula lnt-ll

wherein A¹ , A², A³, A⁴, R³, R⁴, G and n are as defined for the compound of formula I, and R is OH, d- C₆alkoxy, CI, F or Br or a salt or N-oxide thereof. Preferred definitions of A¹ , A², A³, A⁴, R³, R⁴, G and n are as defined for compounds of formula I.

In a further aspect the invention provides compounds of formula Int-lll

wherein A¹ , A², A³, A⁴, R³ and R⁴ are as defined for the compound of formula I, R is d-C₆alkyl or d- C₆alkyl optionally substituted by aryl or a salt or N-oxide thereof. Preferred definitions of A¹, A², A³, A⁴, R³ and R⁴ are as defined for compounds of formula I. Aryl is e.g. phenyl or phenyl optionally substituted by one to three groups selected from cyano, halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₄methoxy or d- dhalomethoxy.

A further group of novel intermediates are compounds of formula Int-IV

wherein A¹ , A², A³, A⁴, R³, R⁴, R^6a and R^6b are as defined for compounds of formula I and R^a and R^b are independently selected from hydrogen, Ci-C₈carbonyl, Ci-C₈alkoxycarbonyl, or R^a and R^b together are - C(=0)-(CH₂)_r-C(=0)- wherein r is 1 to 4, -C(C -C₃alkyl)=C-C=(C₁-C₃alkyl)C-, or group D

or a salt or A/-oxide thereof. The preferred definitions of A¹ , A², A³, A⁴, R³, R⁴, R^6a and R^6b are as defined for compounds of formula I. Preferably R^a and R^b are independently hydrogen, d-C₄carbonyl, d- C₄alkoxycarbonyl, or R^a together are -C(=0)-(CH₂)₂-C(=0)-, -C(CH₃)=C-C=(CH₃)C-, or group D. Most preferably R^a and R^b are independently hydrogen, tert-butoxycarbonyl or R^a and R^b together form group D. Preferably at least one of R^a and R^b is not hydrogen.

A further group of novel intermediates are compounds of formula Int-V

wherein A², A³, A⁴, R³, R⁴, R and n are as defined for compounds of formula I and R^a and R^b, are as defined for the compounds of formula Int-IV. or a salt or A/-oxide thereof. The preferred definitions of A², A³, A⁴, R³, R⁴, R and n are as defined for compounds of formula I. The preferred definitions of R^a and R are as defined for the compounds of formula Int-IV.

A leaving group as referred to herein may be for example a halogen, d-C₈alkoxy, d- C₈alkylsulfonyloxy, Ci-C₈haloalkylsulfonyloxy, Ci-C₈arylsulfonyloxy, optionally substituted d- C₈arylsulfonyloxy (_ary| j_s preferably phenyl), diazonium salts (e.g. -N₂ ⁺ CI^", -N₂ ⁺ BF₄ ^", -N₂ ⁺ Br^", -N₂ ⁺ PF₆ ^_), phosphonate esters (e.g. -OP(0)(OR)_2, wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluoromethylsulfoxy, p-toluenesulfoxy, diazonium chloride.

Tables 1 to 144 below illustrate compounds of the invention.

R5b n R2

1 methyl- 0 methyl- chloro- 0 methyl- bromo- 0 methyl- trifluoromethyl- 0 methyl- methyl- 1 methyl- chloro- 1 methyl- bromo- 1 methyl- trifluoromethyl- 1 methyl- methyl- 2 methyl- chloro- 2 methyl- bromo- 2 methyl- trifluoromethyl- 2 methyl- methyl- 0 ethyl- chloro- 0 ethyl- bromo- 0 ethyl- trifluoromethyl- 0 ethyl- methyl- 1 ethyl- chloro- 1 ethyl- bromo- 1 ethyl- trifluoromethyl- 1 ethyl- methyl- 2 ethyl- chloro- 2 ethyl- bromo- 2 ethyl- trifluoromethyl- 2 ethyl- methyl- 0 2-propyl- chloro- 0 2-propyl- bromo- 0 2-propyl- trifluoromethyl- 0 2-propyl- methyl- 1 2-propyl- chloro- 1 2-propyl- bromo- 1 2-propyl- trifluoromethyl- 1 2-propyl- methyl- 2 2-propyl- chloro- 2 2-propyl- bromo- 2 2-propyl- trifluoromethyl- 2 2-propyl- methyl- 0 n-propyl- chloro- 0 n-propyl- bromo- 0 n-propyl- trifluoromethyl- 0 n-propyl- methyl- 1 n-propyl- chloro- 1 n-propyl- bromo- 1 n-propyl- trifluoromethyl- 1 n-propyl- methyl- 2 n-propyl- chloro- 2 n-propyl- bromo- 2 n-propyl- trifluoromethyl- 2 n-propyl- methyl- 0 n-butyl- chloro- 0 n-butyl- bromo- 0 n-butyl- trifluoromethyl- 0 n-butyl- methyl- 1 n-butyl- chloro- 1 n-butyl- bromo- 1 n-butyl- trifluoromethyl- 1 n-butyl- methyl- 2 n-butyl- chloro- 2 n-butyl- bromo- 2 n-butyl- trifluoromethyl- 2 n-butyl- methyl- 0 s-butyl- chloro- 0 s-butyl- bromo- 0 s-butyl- trifluoromethyl- 0 s-butyl- methyl- 1 s-butyl- chloro- 1 s-butyl- bromo- 1 s-butyl- trifluoromethyl- 1 s-butyl- methyl- 2 s-butyl- chloro- 2 s-butyl- bromo- 2 s-butyl- trifluoromethyl- 2 s-butyl- methyl- 0 t-butyl

chloro- 0 t-butyl

bromo- 0 t-butyl

trifluoromethyl- 0 t-butyl

methyl- 1 t-butyl

chloro- 1 t-butyl

bromo- 1 t-butyl

trifluoromethyl- 1 t-butyl

methyl- 2 t-butyl

chloro- 2 t-butyl

bromo- 2 t-butyl

trifluoromethyl- 2 t-butyl

methyl- 0 2,2,2-trifluoro-ethyl- chloro- 0 2,2,2-trifluoro-ethyl- bromo- 0 2,2,2-trifluoro-ethyl- trifluoromethyl- 0 2,2,2-trifluoro-ethyl- methyl- 1 2,2,2-trifluoro-ethyl- chloro- 1 2,2,2-trifluoro-ethyl- bromo- 1 2,2,2-trifluoro-ethyl- trifluoromethyl- 1 2,2,2-trifluoro-ethyl- methyl- 2 2,2,2-trifluoro-ethyl- 94 chloro- 2 2,2,2-trifluoro-ethyl-

95 bromo- 2 2,2,2-trifluoro-ethyl-

96 trifluoromethyl- 2 2,2,2-trifluoro-ethyl-

97 methyl- 0 2,2-difluoro-ethyl-

98 chloro- 0 2,2-difluoro-ethyl-

99 bromo- 0 2,2-difluoro-ethyl-

100 trifluoromethyl- 0 2,2-difluoro-ethyl-

101 methyl- 1 2,2-difluoro-ethyl-

102 chloro- 1 2,2-difluoro-ethyl-

103 bromo- 1 2,2-difluoro-et yl-

104 trifluoromethyl- 1 2,2-difluoro-ethyl-

105 methyl- 2 2,2-difluoro-ethyl-

106 chloro- 2 2,2-difluoro-ethyl-

107 bromo- 2 2,2-difluoro-ethyl-

108 trifluoromethyl- 2 2,2-difluoro-ethyl-

109 methyl- 0 2-fluoro-ethyl-

1 10 chloro- 0 2-fluoro-ethyl-

1 1 1 bromo- 0 2-fluoro-ethyl-

1 12 trifluoromethyl- 0 2-fluoro-ethyl-

1 13 methyl- 1 2-fluoro-ethyl-

1 14 chloro- 1 2-fluoro-ethyl-

1 15 bromo- 1 2-fluoro-ethyl-

1 16 trifluoromethyl- 1 2-fluoro-ethyl-

1 17 methyl- 2 2-fluoro-ethyl-

1 18 chloro- 2 2-fluoro-ethyl-

1 19 bromo- 2 2-fluoro-ethyl-

120 trifluoromethyl- 2 2-fluoro-ethyl-

121 methyl- 0 2-fluoropropyl-

122 chloro- 0 2-fluoropropyl-

123 bromo- 0 2-fluoropropyl-

124 trifluoromethyl- 0 2-fluoropropyl-

125 methyl- 1 2-fluoropropyl-

126 chloro- 1 2-fluoropropyl-

127 bromo- 1 2-fluoropropyl-

128 trifluoromethyl- 1 2-fluoropropyl-

129 methyl- 2 2-fluoropropyl-

130 chloro- 2 2-fluoropropyl-

131 bromo- 2 2-fluoropropyl-

132 trifluoromethyl- 2 2-fluoropropyl-

133 methyl- 0 3,3,3-trifluoro-propyl-

134 chloro- 0 3,3,3-trifluoro-propyl-

135 bromo- 0 3,3,3-trifluoro-propyl-

136 trifluoromethyl- 0 3,3,3-trifluoro-propyl-

137 methyl- 1 3,3,3-trifluoro-propyl-

138 chloro- 1 3,3,3-trifluoro-propyl-

139 bromo- 1 3,3,3-trifluoro-propyl- 140 trifluoromethyl- 1 3,3,3-trifluoro-propyl-

141 methyl- 2 3,3,3-trifluoro-propyl-

142 chloro- 2 3,3,3-trifluoro-propyl-

143 bromo- 2 3,3, 3-trif I uoro-propy I-

144 trifluoromethyl- 2 3,3,3-trifluoro-propyl-

145 methyl- 0 3,3,3-trifluoro-butyl-

146 chloro- 0 3,3,3-trifluoro-butyl-

147 bromo- 0 3,3,3-trifluoro-butyl-

148 trifluoromethyl- 0 3,3,3-trifluoro-butyl-

149 methyl- 1 3,3, 3-trif I uoro-buty I-

150 chloro- 1 3,3, 3-trif I uoro-buty I-

151 bromo- 1 3,3, 3-trif I uoro-buty I-

152 trifluoromethyl- 1 3,3, 3-trif I uoro-buty I-

153 methyl- 2 3,3,3-trifluoro-butyl-

154 chloro- 2 3,3,3-trifluoro-butyl-

155 bromo- 2 3,3,3-trifluoro-butyl-

156 trifluoromethyl- 2 3,3,3-trifluoro-butyl-

157 methyl- 0 2-cyanoethyl-

158 chloro- 0 2-cyanoethyl-

159 bromo- 0 2-cyanoethyl-

160 trifluoromethyl- 0 2-cyanoethyl-

161 methyl- 1 2-cyanoethyl-

162 chloro- 1 2-cyanoethyl-

163 bromo- 1 2-cyanoethyl-

164 trifluoromethyl- 1 2-cyanoethyl-

165 methyl- 2 2-cyanoethyl-

166 chloro- 2 2-cyanoethyl-

167 bromo- 2 2-cyanoethyl-

168 trifluoromethyl- 2 2-cyanoethyl-

169 methyl- 0 cyanomethyl-

170 c loro- 0 cyanomethyl-

171 bromo- 0 cyanomethyl-

172 trifluoromethyl- 0 cyanomethyl-

173 methyl- 1 cyanomethyl-

174 chloro- 1 cyanomethyl-

175 bromo- 1 cyanomethyl-

176 trifluoromethyl- 1 cyanomethyl-

177 methyl- 2 cyanomethyl-

178 chloro- 2 cyanomethyl-

179 bromo- 2 cyanomethyl-

180 trifluoromethyl- 2 cyanomethyl-

181 methyl- 0 2-cyano-propan-2yl-

182 chloro- 0 2-cyano-propan-2yl-

183 bromo- 0 2-cyano-propan-2yl-

184 trifluoromethyl- 0 2-cyano-propan-2yl-

185 methyl- 1 2-cyano-propan-2yl- 186 chloro- 1 2-cyano-propan-2yl-

187 bromo- 1 2-cyano-propan-2yl-

188 trifluoromethyl- 1 2-cyano-propan-2yl-

189 methyl- 2 2-cyano-propan-2yl-

190 chloro- 2 2-cyano-propan-2yl-

191 bromo- 2 2-cyano-propan-2yl-

192 trifluoromethyl- 2 2-cyano-propan-2yl-

193 methyl- 0 1 -methoxy-prop-2-yl-

194 chloro- 0 1 -methoxy-prop-2-yl-

195 bromo- 0 1-methoxy-prop-2-yl-

196 trifluoromethyl- 0 1 -methoxy-prop-2-yl-

197 methyl- 1 1-methoxy-prop-2-yl-

198 chloro- 1 1 -methoxy-prop-2-yl-

199 bromo- 1 1 -methoxy-prop-2-yl-

200 trifluoromethyl- 1 1 -methoxy-prop-2-yl-

201 methyl- 2 1 -methoxy-prop-2-yl-

202 chloro- 2 1 -methoxy-prop-2-yl-

203 bromo- 2 1-methoxy-prop-2-yl-

204 trifluoromethyl- 2 1 -methoxy-prop-2-yl-

205 methyl- 0 2-methylsulfanyl-ethyl-

206 chloro- 0 2-methylsulfanyl-ethyl-

207 bromo- 0 2-m ethylsu Ifanyl-ethyl-

208 trifluoromethyl- 0 2-methylsulfanyl-ethyl-

209 methyl- 1 2-methylsulfanyl-ethyl-

210 chloro- 1 2-methylsulfanyl-ethyl-

21 1 bromo- 1 2-methylsulfanyl-ethyl-

212 trifluoromethyl- 1 2-methylsulfanyl-ethyl-

213 methyl- 2 2-m ethylsu Ifanyl-ethyl-

214 chloro- 2 2-methylsulfanyl-ethyl-

215 bromo- 2 2-methylsulfanyl-ethyl-

216 trifluoromethyl- 2 2-methylsulfanyl-ethyl-

217 methyl- 0 2-methylsulfanyl-prop-3-yl-

218 chloro- 0 2-methylsulfanyl-prop-3-yl-

219 bromo- 0 2-methylsulfanyl-prop-3-yl-

220 trifluoromethyl- 0 2-methylsulfanyl-prop-3-yl-

221 methyl- 1 2-methylsulfanyl-prop-3-yl-

222 chloro- 1 2-methylsulfanyl-prop-3-yl-

223 bromo- 1 2-methylsulfanyl-prop-3-yl-

224 trifluoromethyl- 1 2-methylsulfanyl-prop-3-yl-

225 methyl- 2 2-methylsulfanyl-prop-3-yl-

226 chloro- 2 2-methylsulfanyl-prop-3-yl-

227 bromo- 2 2-methylsulfanyl-prop-3-yl-

228 trifluoromethyl- 2 2-methylsulfanyl-prop-3-yl-

229 methyl- 0 allyl-

230 chloro- 0 allyl-

231 bromo- 0 allyl- 232 trifluoromethyl- 0 allyl-

233 methyl- 1 allyl-

234 chloro- 1 allyl-

235 bromo- 1 allyl-

236 trifluoromethyl- 1 allyl-

237 methyl- 2 allyl-

238 chloro- 2 allyl-

239 bromo- 2 allyl-

240 trifluoromethyl- 2 allyl-

241 methyl- 0 3,3-dichloroallyl-

242 chloro- 0 3,3-dichloroallyl-

243 bromo- 0 3,3-dichloroallyl-

244 trifluoromethyl- 0 3,3-dichloroallyl-

245 methyl- 1 3,3-dichloroallyl-

246 chloro- 1 3,3-dichloroallyl-

247 bromo- 1 3,3-dichloroallyl-

248 trifluoromethyl- 1 3,3-dichloroallyl-

249 methyl- 2 3,3-dichloroallyl-

250 chloro- 2 3,3-dichloroallyl-

251 bromo- 2 3,3-dichloroallyl-

252 trifluoromethyl- 2 3,3-dichloroallyl-

253 methyl- 0 2-butenyl-

254 chloro- 0 2-butenyl-

255 bromo- 0 2-butenyl-

256 trifluoromethyl- 0 2-butenyl-

257 methyl- 1 2-butenyl-

258 chloro- 1 2-butenyl-

259 bromo- 1 2-butenyl-

260 trifluoromethyl- 1 2-butenyl-

261 methyl- 2 2-butenyl-

262 chloro- 2 2-butenyl-

263 bromo- 2 2-butenyl-

264 trifluoromethyl- 2 2-butenyl-

265 methyl- 0 2-chloroallyl-

266 chloro- 0 2-chloroallyl-

267 bromo- 0 2-chloroallyl-

268 trifluoromethyl- 0 2-chloroallyl-

269 methyl- 1 2-chloroallyl-

270 chloro- 1 2-chloroallyl-

271 bromo- 1 2-chloroallyl-

272 trifluoromethyl- 1 2-chloroallyl-

273 methyl- 2 2-chloroallyl-

274 chloro- 2 2-chloroallyl-

275 bromo- 2 2-chloroallyl-

276 trifluoromethyl- 2 2-chloroallyl-

277 methyl- 0 propargyl- 278 chloro- 0 propargyl-

279 bromo- 0 propargyl-

280 trifluoromethyl- 0 propargyl-

281 methyl- 1 propargyl-

282 chloro- 1 propargyl-

283 bromo- 1 propargyl-

284 trifluoromethyl- 1 propargyl-

285 methyl- 2 propargyl-

286 chloro- 2 propargyl-

287 bromo- 2 propargyl-

288 trifluoromethyl- 2 propargyl-

289 methyl- 0 but-2-ynyl-

290 chloro- 0 but-2-ynyl-

291 bromo- 0 but-2-ynyl-

292 trifluoromethyl- 0 but-2-ynyl-

293 methyl- 1 but-2-ynyl-

294 chloro- 1 but-2-ynyl-

295 bromo- 1 but-2-ynyl-

296 trifluoromethyl- 1 but-2-ynyl-

297 methyl- 2 but-2-ynyl-

298 chloro- 2 but-2-ynyl-

299 bromo- 2 but-2-ynyl-

300 trifluoromethyl- 2 but-2-ynyl-

301 methyl- 0 but-3-ynyl-

302 chloro- 0 but-3-ynyl-

303 bromo- 0 but-3-ynyl-

304 trifluoromethyl- 0 but-3-ynyl-

305 methyl- 1 but-3-ynyl-

306 chloro- 1 but-3-ynyl-

307 bromo- 1 but-3-ynyl-

308 trifluoromethyl- 1 but-3-ynyl-

309 methyl- 2 but-3-ynyl-

310 chloro- 2 but-3-ynyl-

31 1 bromo- 2 but-3-ynyl-

312 trifluoromethyl- 2 but-3-ynyl-

313 methyl- 0 benzyl-

314 chloro- 0 benzyl-

315 bromo- 0 benzyl-

316 trifluoromethyl- 0 benzyl-

317 methyl- 1 benzyl-

318 chloro- 1 benzyl-

319 bromo- 1 benzyl-

320 trifluoromethyl- 1 benzyl-

321 methyl- 2 benzyl-

322 chloro- 2 benzyl-

323 bromo- 2 benzyl- 324 trifluoromethyl- 2 benzyl-

325 methyl- 0 cyclopropyl-

326 chloro- 0 cyclopropyl-

327 bromo- 0 cyclopropyl-

328 trifluoromethyl- 0 cyclopropyl-

329 methyl- 1 cyclopropyl-

330 chloro- 1 cyclopropyl-

331 bromo- 1 cyclopropyl-

332 trifluoromethyl- 1 cyclopropyl-

333 methyl- 2 cyclopropyl-

334 chloro- 2 cyclopropyl-

335 bromo- 2 cyclopropyl-

336 trifluoromethyl- 2 cyclopropyl-

337 methyl- 0 cyclobutyl-

338 chloro- 0 cyclobutyl-

339 bromo- 0 cyclobutyl-

340 trifluoromethyl- 0 cyclobutyl-

341 methyl- 1 cyclobutyl-

342 chloro- 1 cyclobutyl-

343 bromo- 1 cyclobutyl-

344 trifluoromethyl- 1 cyclobutyl-

345 methyl- 2 cyclobutyl-

346 chloro- 2 cyclobutyl-

347 bromo- 2 cyclobutyl-

348 trifluoromethyl- 2 cyclobutyl-

349 methyl- 0 cyclopentyl-

350 chloro- 0 cyclopentyl-

351 bromo- 0 cyclopentyl-

352 trifluoromethyl- 0 cyclopentyl-

353 methyl- 1 cyclopentyl-

354 chloro- 1 cyclopentyl-

355 bromo- 1 cyclopentyl-

356 trifluoromethyl- 1 cyclopentyl-

357 methyl- 2 cyclopentyl-

358 chloro- 2 cyclopentyl-

359 bromo- 2 cyclopentyl-

360 trifluoromethyl- 2 cyclopentyl-

361 methyl- 0 cyclopropyl-methyl-

362 chloro- 0 cyclopropyl-methyl-

363 bromo- 0 cyclopropyl-methyl-

364 trifluoromethyl- 0 cyclopropyl-methyl-

365 methyl- 1 cyclopropyl-methyl-

366 chloro- 1 cyclopropyl-methyl-

367 bromo- 1 cyclopropyl-methyl-

368 trifluoromethyl- 1 cyclopropyl-methyl-

369 methyl- 2 cyclopropyl-methyl- 370 chloro- 2 cyclopropyl-methyl-

371 bromo- 2 cyclopropyl-methyl-

372 trifluoromethyl- 2 cyclopropyl-methyl-

373 methyl- 0 cyclobutyl-methyl-

374 chloro- 0 cyclobutyl-methyl-

375 bromo- 0 cyclobutyl-methyl-

376 trifluoromethyl- 0 cyclobutyl-methyl-

377 methyl- 1 cyclobutyl-methyl-

378 chloro- 1 cyclobutyl-methyl-

379 bromo- 1 cyclobutyl-methyl-

380 trifluoromethyl- 1 cyclobutyl-methyl-

381 methyl- 2 cyclobutyl-methyl-

382 chloro- 2 cyclobutyl-methyl-

383 bromo- 2 cyclobutyl-methyl-

384 trifluoromethyl- 2 cyclobutyl-methyl-

385 methyl- 0 thietan-3-yl-

386 chloro- 0 thietan-3-yl-

387 bromo- 0 thietan-3-yl-

388 trifluoromethyl- 0 thietan-3-yl-

389 methyl- 1 thietan-3-yl-

390 chloro- 1 thietan-3-yl-

391 bromo- 1 thietan-3-yl-

392 trifluoromethyl- 1 thietan-3-yl-

393 methyl- 2 thietan-3-yl-

394 chloro- 2 thietan-3-yl-

395 bromo- 2 thietan-3-yl-

396 trifluoromethyl- 2 thietan-3-yl-

397 methyl- 0 1-oxo-thietan-3-yl-

398 chloro- 0 1-oxo-thietan-3-yl-

399 bromo- 0 1-oxo-thietan-3-yl-

400 trifluoromethyl- 0 1-oxo-thietan-3-yl-

401 methyl- 1 1-oxo-thietan-3-yl-

402 chloro- 1 1-oxo-thietan-3-yl-

403 bromo- 1 1-oxo-thietan-3-yl-

404 trifluoromethyl- 1 1-oxo-thietan-3-yl-

405 methyl- 2 1-oxo-thietan-3-yl-

406 chloro- 2 1-oxo-thietan-3-yl-

407 bromo- 2 1-oxo-thietan-3-yl-

408 trifluoromethyl- 2 1-oxo-thietan-3-yl-

409 methyl- 0 1 , 1-dioxo-thietan-3-yl-

410 chloro- 0 1 , 1-dioxo-thietan-3-yl-

41 1 bromo- 0 1 , 1-dioxo-thietan-3-yl-

412 trifluoromethyl- 0 1 , 1-dioxo-thietan-3-yl-

413 methyl- 1 1 , 1-dioxo-thietan-3-yl-

414 chloro- 1 1 , 1-dioxo-thietan-3-yl-

415 bromo- 1 1 , 1-dioxo-thietan-3-yl- 416 trifluoromethyl- 1 1 , 1-dioxo-thietan-3-yl-

417 methyl- 2 1 , 1-dioxo-thietan-3-yl-

418 chloro- 2 1 , 1-dioxo-thietan-3-yl-

419 bromo- 2 , -dioxo-thietan-3-yl-

420 trifluoromethyl- 2 1 , 1-dioxo-thietan-3-yl-

421 methyl- 0 3-methyl-thietan-3-yl-

422 chloro- 0 3-methyl-thietan-3-yl-

423 bromo- 0 3-methyl-thietan-3-yl-

424 trifluoromethyl- 0 3-methyl-thietan-3-yl-

425 methyl- 1 3-methyl-thietan-3-yl-

426 chloro- 1 3-methyl-thietan-3-yl-

427 bromo- 1 3-methyl-thietan-3-yl-

428 trifluoromethyl- 1 3-methyl-thietan-3-yl-

429 methyl- 2 3-methyl-thietan-3-yl-

430 chloro- 2 3-methyl-thietan-3-yl-

431 bromo- 2 3-methyl-thietan-3-yl-

432 trifluoromethyl- 2 3-methyl-thietan-3-yl-

433 methyl- 0 thietan-3-ylmethyl-

434 chloro- 0 thietan-3-ylmethyl-

435 bromo- 0 thietan-3-ylmethyl-

436 trifluoromethyl- 0 thietan-3-ylmethyl-

437 methyl- 1 thietan-3-ylmethyl-

438 chloro- 1 thietan-3-ylmethyl-

439 bromo- 1 thietan-3-ylmethyl-

440 trifluoromethyl- 1 thietan-3-ylmethyl-

441 methyl- 2 thietan-3-ylmethyl-

442 chloro- 2 thietan-3-ylmethyl-

443 bromo- 2 thietan-3-ylmethyl-

444 trifluoromethyl- 2 thietan-3-ylmethyl-

445 methyl- 0 (1 , 1-dioxothietan-3-yl)methyl-

446 chloro- 0 ( 1 , 1 -d ioxoth ietan-3-y l)methyl-

447 bromo- 0 ( 1 , 1 -d ioxoth ietan-3-yl)methyl-

448 trifluoromethyl- 0 ( 1 , 1 -d ioxoth ietan-3-yl)methyl-

449 methyl- 1 ( 1 , 1 -d ioxoth ietan-3-yl)methyl-

450 chloro- 1 ( 1 , 1 -d ioxoth ietan-3-yl)methyl-

451 bromo- 1 (1 , 1-dioxothietan-3-yl)methyl-

452 trifluoromethyl- 1 ( 1 , 1 -d ioxoth ietan-3-y l)methyl-

453 methyl- 2 ( 1 , 1 -d ioxoth ietan-3-y l)methyl-

454 chloro- 2 ( 1 , 1 -d ioxoth ietan-3-yl)methyl-

455 bromo- 2 ( 1 , 1 -d ioxoth ietan-3-yl)methyl-

456 trifluoromethyl- 2 ( 1 , 1 -d ioxoth ietan-3-yl)methyl-

457 methyl- 0 ( -oxothietan-3-yl)methyl-

458 chloro- 0 ( 1 -oxothietan-3-yl)methyl-

459 bromo- 0 ( 1 -oxothietan-3-yl)methyl-

460 trifluoromethyl- 0 ( 1 -oxothietan-3-yl)methyl-

461 methyl- 1 ( 1 -oxothietan-3-yl)methyl- _

462 chloro- 1 ( 1 -oxothietan-3-yl)methyl-

463 bromo- 1 ( 1 -oxothietan-3-yl)methyl-

464 trifluoromethyl- 1 ( 1 -oxothietan-3-yl)methyl-

465 methyl- 2 ( 1 -oxothietan-3-yl)methyl-

466 chloro- 2 ( 1 -oxothietan-3-yl)methyl-

467 bromo- 2 (1-oxothietan-3-yl)methyl-

468 trifluoromethyl- 2 ( 1 -oxothietan-3-yl)methyl-

469 methyl- 0 cis-1-oxo-thietan-3-yl-

470 chloro- 0 cis-1-oxo-thietan-3-yl-

471 bromo- 0 cis-1-oxo-thietan-3-yl-

472 trifluoromethyl- 0 cis-1-oxo-thietan-3-yl-

473 methyl- 1 cis-1-oxo-thietan-3-yl-

474 chloro- 1 cis- -oxo-thietan-3-yl-

475 bromo- 1 cis-1-oxo-thietan-3-yl-

476 trifluoromethyl- 1 cis-1-oxo-thietan-3-yl-

477 methyl- 2 cis-1-oxo-thietan-3-yl-

478 chloro- 2 cis-1-oxo-thietan-3-yl-

479 bromo- 2 cis-1-oxo-thietan-3-yl-

480 trifluoromethyl- 2 cis-1-oxo-thietan-3-yl-

481 methyl- 0 cis-1-oxo-thietan-3-ylmethyl-

482 chloro- 0 cis-1-oxo-thietan-3-ylmethyl-

483 bromo- 0 cis-1-oxo-thietan-3-ylmethyl-

484 trifluoromethyl- 0 cis-1-oxo-thietan-3-ylmethyl-

485 met yl- 1 cis-1-oxo-thietan-3-ylmethyl-

486 chloro- 1 cis-1-oxo-thietan-3-ylmethyl-

487 bromo- 1 cis-1-oxo-thietan-3-ylmethyl-

488 trifluoromethyl- 1 cis-1-oxo-thietan-3-ylmethyl-

489 methyl- 2 cis-1-oxo-thietan-3-ylmethyl-

490 chloro- 2 cis-1-oxo-thietan-3-ylmethyl-

491 bromo- 2 cis-1-oxo-thietan-3-ylmethyl-

492 trifluoromethyl- 2 cis-1-oxo-thietan-3-ylmethyl-

493 met yl- 0 (pyrid-2-yl)-methyl-

494 chloro- 0 (pyrid-2-yl)-met yl-

495 bromo- 0 (pyrid-2-yl)-methyl-

496 trifluoromethyl- 0 (pyrid-2-yl)-methyl-

497 methyl- 1 (pyrid-2-yl)-methyl-

498 chloro- 1 (pyrid-2-yl)-methyl-

499 bromo- 1 (pyrid-2-yl)-methyl-

500 trifluoromethyl- 1 (pyrid-2-yl)-methyl-

501 met yl- 2 (pyrid-2-yl)-methyl-

502 chloro- 2 (pyrid-2-yl)-methyl-

503 bromo- 2 (pyrid-2-yl)-methyl-

504 trifluoromethyl- 2 (pyrid-2-yl)-methyl-

505 methyl- 0 (pyrid-3-yl)-methyl-

506 chloro- 0 (pyrid-3-yl)-methyl-

507 bromo- 0 (pyrid-3-yl)-m ethyl- 508 trifluoromethyl- 0 (pyrid-3-yl)-methyl-

509 methyl- 1 (pyrid-3-yl)-methyl-

510 chloro- 1 (pyrid-3-yl)-methyl-

51 1 bromo- 1 (pyrid-3-yl)-methyl-

512 trifluoromethyl- 1 (pyrid-3-yl)-methyl-

513 methyl- 2 (pyrid-3-yl)-methyl-

514 chloro- 2 (pyrid-3-yl)-methyl-

515 bromo- 2 (pyrid-3-yl)-methyl-

516 trifluoromet yl- 2 (pyrid-3-yl)-met yl-

517 methyl- 0 (pyrid-4-yl)-methyl-

518 chloro- 0 (pyrid-4-yl)-methyl-

519 bromo- 0 (pyrid-4-yl)-methyl-

520 trifluoromethyl- 0 (pyrid-4-yl)-methyl-

521 methyl- 1 (pyrid-4-yl)-methyl-

522 chloro- 1 (pyrid-4-yl)-methyl-

523 bromo- 1 (pyrid-4-yl)-methyl-

524 trifluoromethyl- 1 (pyrid-4-yl)-methyl-

525 methyl- 2 (pyrid-4-yl)-methyl-

526 chloro- 2 (pyrid-4-yl)-methyl-

527 bromo- 2 (pyrid-4-yl)-methyl-

528 trifluoromethyl- 2 (pyrid-4-yl)-methyl-

529 methyl- 0 oxetan-3yl-

530 chloro- 0 oxetan-3yl-

531 bromo- 0 oxetan-3yl-

532 trifluoromethyl- 0 oxetan-3yl-

533 methyl- 1 oxetan-3yl-

534 chloro- 1 oxetan-3yl-

535 bromo- 1 oxetan-3yl-

536 trifluoromethyl- 1 oxetan-3yl-

537 methyl- 2 oxetan-3yl-

538 chloro- 2 oxetan-3yl-

539 bromo- 2 oxetan-3yl-

540 trifluoromethyl- 2 oxetan-3yl-

541 methyl- 0 oxetan-3ylmethyl

542 chloro- 0 oxetan-3ylmethyl

543 bromo- 0 oxetan-3ylmethyl

544 trifluoromethyl- 0 oxetan-3ylmethyl

545 methyl- 1 oxetan-3ylmethyl

546 chloro- 1 oxetan-3ylmethyl

547 bromo- 1 oxetan-3ylmethyl

548 trifluoromethyl- 1 oxetan-3ylmethyl

549 methyl- 2 oxetan-3ylmethyl

550 chloro- 2 oxetan-3ylmethyl

551 bromo- 2 oxetan-3ylmethyl

552 trifluoromethyl- 2 oxetan-3ylmethyl

553 methyl- 0 (tetrahydrofuran-2-yl)-methyl- 554 chloro- 0 (tetrahydrofuran-2-yl)-methyl-

555 bromo- 0 (tetrahydrofuran-2-yl)-methyl-

556 trifluoromethyl- 0 (tetrahydrofuran-2-yl)-methyl-

557 methyl- 1 (tetrahydrofuran-2-yl)-methyl-

558 chloro- 1 (tetrahydrofuran-2-yl)-methyl-

559 bromo- 1 (tetrahydrofuran-2-yl)-methyl-

560 trifluoromethyl- 1 (tetrahydrofuran-2-yl)-methyl-

561 methyl- 2 (tetrahydrofuran-2-yl)-methyl-

562 chloro- 2 (tetrahydrofuran-2-yl)-methyl-

563 bromo- 2 (tetrahydrofuran-2-yl)-methyl-

564 trifluoromethyl- 2 (tetrahydrofuran-2-yl)-methyl-

565 methyl- 0 (tetrahydrofuran-3-yl)-methyl-

566 chloro- 0 (tetrahydrofuran-3-yl)-methyl-

567 bromo- 0 (tetrahydrofuran-3-yl)-methyl-

568 trifluoromethyl- 0 (tetrahydrofuran-3-yl)-methyl-

569 methyl- 1 (tetrahydrofuran-3-yl)-methyl-

570 chloro- 1 (tetrahydrofuran-3-yl)-methyl-

571 bromo- 1 (tetrahydrofuran-3-yl)-methyl-

572 trifluoromethyl- 1 (tetrahydrofuran-3-yl)-methyl-

573 methyl- 2 (tetrahydrofuran-3-yl)-methyl-

574 chloro- 2 (tetrahydrofuran-3-yl)-methyl-

575 bromo- 2 (tetrahydrofuran-3-yl)-methyl-

576 trifluoromethyl- 2 (tetrahydrofuran-3-yl)-met yl-

577 methyl- 0 (4-fluorophenyl)-methyl-

578 chloro- 0 (4-fluorophenyl)-methyl-

579 bromo- 0 (4-fluorophenyl)-methyl-

580 trifluoromethyl- 0 (4-fluorophenyl)-methyl-

581 methyl- 1 (4-fluorophenyl)-methyl-

582 chloro- 1 (4-fluorophenyl)-methyl-

583 bromo- 1 (4-fluorophenyl)-methyl-

584 trifluoromethyl- 1 (4-fluorophenyl)-methyl-

585 methyl- 2 (4-fluorophenyl)-methyl-

586 chloro- 2 (4-fluorophenyl)-methyl-

587 bromo- 2 (4-fluorophenyl)-methyl-

588 trifluoromethyl- 2 (4-fluorophenyl)-methyl-

589 methyl- 0 (4-chlorophenyl)-methyl-

590 chloro- 0 (4-chlorophenyl)-methyl-

591 bromo- 0 (4-chlorophenyl)-methyl-

592 trifluoromethyl- 0 (4-chlorophenyl)-methyl-

593 methyl- 1 (4-chlorophenyl)-methyl-

594 chloro- 1 (4-chlorophenyl)-methyl-

595 bromo- 1 (4-chlorophenyl)-methyl-

596 trifluoromethyl- 1 (4-chlorophenyl)-methyl-

597 methyl- 2 (4-chlorophenyl)-methyl-

598 chloro- 2 (4-chlorophenyl)-methyl-

599 bromo- 2 (4-chlorophenyl)-m ethyl- 600 trifluoromethyl- 2 (4-chlorophenyl)-methyl-

601 methyl- 0 4-fluorophenyl-

602 chloro- 0 4-fluorophenyl-

603 bromo- 0 4-fluorophenyl-

604 trifluoromethyl- 0 4-fluorophenyl-

605 methyl- 1 4-fluorophenyl-

606 chloro- 1 4-fluorophenyl-

607 bromo- 1 4-fluorophenyl-

608 trifluoromethyl- 1 4-fluorophenyl-

609 methyl- 2 4-fluorophenyl-

610 chloro- 2 4-fluorophenyl-

61 1 bromo- 2 4-fluorophenyl-

612 trifluoromethyl- 2 4-fluorophenyl-

613 methyl- 0 4-chlorophenyl-

614 chloro- 0 4-chlorophenyl-

615 bromo- 0 4-chlorophenyl-

616 trifluoromethyl- 0 4-chlorophenyl-

617 methyl- 1 4-chlorophenyl-

618 chloro- 1 4-chlorophenyl-

619 bromo- 1 4-chlorophenyl-

620 trifluoromethyl- 1 4-chlorophenyl-

621 methyl- 2 4-chlorophenyl-

622 chloro- 2 4-chlorop enyl-

623 bromo- 2 4-chlorophenyl-

624 trifluoromethyl- 2 4-chlorophenyl-

625 methyl- 0 2-furylmethyl-

626 chloro- 0 2-furylmethyl-

627 bromo- 0 2-furylmethyl-

628 trifluoromethyl- 0 2-furylmethyl-

629 methyl- 1 2-furylmethyl-

630 chloro- 1 2-furylmethyl-

631 bromo- 1 2-furylmethyl-

632 trifluoromethyl- 1 2-furylmethyl-

633 methyl- 2 2-furylmethyl-

634 chloro- 2 2-furylmethyl-

635 bromo- 2 2-furylmethyl-

636 trifluoromethyl- 2 2-furylmethyl-

637 methyl- 0 (4-chloro-pyrid-2-yl)-methyl-

638 chloro- 0 (4-chloro-pyrid-2-yl)-methyl-

639 bromo- 0 (4-chloro-pyrid-2-yl)-methyl-

640 trifluoromethyl- 0 (4-chloro-pyrid-2-yl)-methyl-

641 methyl- 1 (4-chloro-pyrid-2-yl)-methyl-

642 chloro- 1 (4-chloro-pyrid-2-yl)-methyl-

643 bromo- 1 (4-chloro-pyrid-2-yl)-methyl-

644 trifluoromethyl- 1 (4-chloro-pyrid-2-yl)-methyl-

645 methyl- 2 (4-chloro-pyrid-2-yl)-methyl- 646 chloro- 2 (4-chloro-pyrid-2-yl)-methyl-

647 bromo- 2 (4-chloro-pyrid-2-yl)-methyl-

648 trifluoromethyl- 2 (4-chloro-pyrid-2-yl)-methyl-

649 methyl- 0 (4-chloro-pyrid-3-yl)-methyl-

650 chloro- 0 (4-chloro-pyrid-3-yl)-methyl-

651 bromo- 0 (4-chloro-pyrid-3-yl)-methyl-

652 trifluoromethyl- 0 (4-chloro-pyrid-3-yl)-methyl-

653 methyl- 1 (4-chloro-pyrid-3-yl)-methyl-

654 chloro- 1 (4-chloro-pyrid-3-yl)-methyl-

655 bromo- 1 (4-chloro-pyrid-3-yl)-methyl-

656 trifluoromethyl- 1 (4-chloro-pyrid-3-yl)-methyl-

657 methyl- 2 (4-chloro-pyrid-3-yl)-methyl-

658 chloro- 2 (4-chloro-pyrid-3-yl)-methyl-

659 bromo- 2 (4-chloro-pyrid-3-yl)-methyl-

660 trifluoromethyl- 2 (4-chloro-pyrid-3-yl)-methyl-

661 methyl- 0 (3-chloro-pyrid-4-yl)-methyl-

662 chloro- 0 (3-chloro-pyrid-4-yl)-methyl-

663 bromo- 0 (3-chloro-pyrid-4-yl)-methyl-

664 trifluoromethyl- 0 (3-chloro-pyrid-4-yl)-methyl-

665 methyl- 1 (3-chloro-pyrid-4-yl)-methyl-

666 chloro- 1 (3-chloro-pyrid-4-yl)-methyl-

667 bromo- 1 (3-chloro-pyrid-4-yl)-methyl-

668 trifluoromethyl- 1 (3-chloro-pyrid-4-yl)-met yl-

669 methyl- 2 (3-chloro-pyrid-4-yl)-methyl-

670 chloro- 2 (3-chloro-pyrid-4-yl)-methyl-

671 bromo- 2 (3-chloro-pyrid-4-yl)-methyl-

672 trifluoromethyl- 2 (3-chloro-pyrid-4-yl)-methyl-

673 methyl- 0 2-cyano-ethyl

674 chloro- 0 2-cya no-ethyl

675 bromo- 0 2-cyano-ethyl

676 trifluoromethyl- 0 2-cyano-ethyl

677 methyl- 1 2-cyano-ethyl

678 chloro- 1 2-cyano-ethyl

679 bromo- 1 2-cyano-ethyl

680 trifluoromethyl- 1 2-cyano-ethyl

681 methyl- 2 2-cyano-ethyl

682 chloro- 2 2-cyano-ethyl

683 bromo- 2 2-cyano-ethyl

684 trifluoromethyl- 2 2-cyano-ethyl

685 methyl- 0 2-methoxy-ethyl-

686 chloro- 0 2-methoxy-ethyl-

687 bromo- 0 2-methoxy-ethyl-

688 trifluoromethyl- 0 2-methoxy-ethyl-

689 methyl- 1 2-methoxy-ethyl-

690 chloro- 1 2-methoxy-ethyl-

691 bromo- 1 2-methoxy-ethyl- 692 trifluoromethyl- 1 2-methoxy-ethyl-

693 methyl- 2 2-methoxy-ethyl-

694 chloro- 2 2-methoxy-ethyl-

695 bromo- 2 2-methoxy-ethyl-

696 trifluoromethyl- 2 2-methoxy-ethyl-

697 methyl- 0 1-methylthio-prop-2-yl-

698 chloro- 0 1-methylthio-prop-2-yl-

699 bromo- 0 1-methylthio-prop-2-yl-

700 trifluoromethyl- 0 1 -m ethylth io-prop-2-yl-

701 methyl- 1 1 -m ethylth io-prop-2-yl-

702 chloro- 1 1 -m ethylth io-prop-2-yl-

703 bromo- 1 1 -m ethylth io-prop-2-yl-

704 trifluoromethyl- 1 1 -m ethylth io-prop-2-yl-

705 methyl- 2 1-m ethylth io-prop-2-yl-

706 chloro- 2 1 -m ethylth io-prop-2-yl-

707 bromo- 2 1 -m ethylth io-prop-2-yl-

708 trifluoromethyl- 2 1-methylthio-prop-2-yl-

709 methyl- 0 2-m ethylth io-ethyl-

710 chloro- 0 2-m ethylth io-ethyl-

71 1 bromo- 0 2-m ethylth io-ethyl-

712 trifluoromethyl- 0 2-m ethylth io-ethyl-

713 methyl- 1 2-m ethylth io-ethyl-

714 chloro- 1 2-methylthio-ethyl-

715 bromo- 1 2-m ethylth io-ethyl-

716 trifluoromethyl- 1 2-m ethylth io-ethyl-

717 methyl- 2 2-m ethylth io-ethyl-

718 chloro- 2 2-m ethylth io-ethyl-

719 bromo- 2 2-m ethylth io-ethyl-

720 trifluoromethyl- 2 2-methylthio-ethyl-

Table 1 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 2

Table 2 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 3

Table 3 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 4 Table 4 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 5

Table 5 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 6

Table 6 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 7

Table 7 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 8

Table 8 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 9

Table 9 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 10

Table 10 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is

3.4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 11

Table 11 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 12

Table 12 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 13

Table 13 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is

3.5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 14

Table 14 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 15

Table 15 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 16

Table 16 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 17

Table 17 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 18

Table 18 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 19

Table 19 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 20

Table 20 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 21

Table 21 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,4,5- trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 22 Table 22 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 23

Table 23 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 24

Table 24 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,4,5- trichlorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 25

Table 25 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 26

Table 26 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 27

Table 27 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 28

Table 28 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 29

Table 29 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 30

Table 30 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 31

Table 31 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 32

Table 32 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 33

Table 33 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 34

Table 34 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 35

Table 35 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 36

Table 36 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 37

Table 37 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 38

Table 38 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P. Table 39

Table 39 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 40

Table 40 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 41

Table 41 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 42

Table 42 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 43

Table 43 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 44

Table 44 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 45

Table 45 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 46

Table 46 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 47

Table 47 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 48

Table 48 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 49

Table 49 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 50

Table 50 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 51

Table 51 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 52

Table 52 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 53

Table 53 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 54

Table 54 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 55

Table 55 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 56

Table 56 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 57 Table 57 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 58

Table 58 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is

3.4- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 59

Table 59 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 60

Table 60 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 61

Table 61 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is

3.5- dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 62

Table 62 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 63

Table 63 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 64

Table 64 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 65

Table 65 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 66

Table 66 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 67

Table 67 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 68

Table 68 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 69

Table 69 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,4,5- trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 70

Table 70 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 71

Table 71 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 72

Table 72 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,4,5- trichlorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 73

Table 73 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 74

Table 74 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 75

Table 75 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P. Table 76

Table 76 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 77

Table 77 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 78

Table 78 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 79

Table 79 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 80

Table 80 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 81

Table 81 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 82

Table 82 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 83

Table 83 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 84

Table 84 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 85

Table 85 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 86

Table 86 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 87

Table 87 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 88

Table 88 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 89

Table 89 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 90

Table 90 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 91

Table 91 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 92 Table 92 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 93

Table 93 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 94

Table 94 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 95

Table 95 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 96

Table 96 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is N, A4 is CH, and R5b, n and R2 are as defined in Table P.

Table 97

Table 97 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 98

Table 98 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 99

Table 99 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 100

Table 100 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 101

Table 101 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,5-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 102

Table 102 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,5- dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 103

Table 103 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 104

Table 104 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 105

Table 105 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 106

Table 106 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,4-dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 107

Table 107 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is

3.4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 108

Table 108 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,4- dichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 109

Table 109 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is

3.5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 110

Table 110 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P. Table 1 11

Table 111 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 1 12

Table 112 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 1 13

Table 113 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,5-dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 1 14

Table 114 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,5- dichloro-4-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 1 15

Table 115 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 1 16

Table 116 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 1 17

Table 117 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 1 18

Table 118 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 1 19

Table 119 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 120

Table 120 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,4,5-trichlorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 121

Table 121 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 122

Table 122 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 123

Table 123 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 124

Table 124 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3-chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 125

Table 125 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 126

Table 126 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-fluorophenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 127

Table 127 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 128

Table 128 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P. Table 129

Table 129 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 130

Table 130 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3-chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 131

Table 131 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 132

Table 132 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3- chloro-5-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 133

Table 133 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 134

Table 134 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 135

Table 135 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 136

Table 136 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 137

Table 137 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3,5-bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 138

Table 138 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3,5- bis(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 139

Table 139 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is trifluoromethyl-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 140

Table 140 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 141

Table 141 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is trifluoromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 142

Table 142 provides 720 compounds of formula IA wherein R1 is hydrogen, R3 is dichloromethyl-, R4 is 3-(trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 143

Table 143 provides 720 compounds of formula IA wherein R1 is methyl-, R3 is dichloromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P.

Table 144

Table 144 provides 720 compounds of formula IA wherein R1 is ethyl-, R3 is dichloromethyl-, R4 is 3- (trifluoromethyl)phenyl-, A2 is CH, A3 is CH, A4 is N, and R5b, n and R2 are as defined in Table P. Table Q

Table Q96

Table Q96 provides 18 compounds of formula l-B wherein R10 is 2-methoxy-ethyl- and R3 and R4 are as defined in Table QQ.

Table Q97

Table Q97 provides 18 compounds of formula l-B wherein R10 is 2-(methylsulfonyl)-ethyl- and R3 and R4 are as defined in Table QQ.

Table Q98

Table Q98 provides 18 compounds of formula l-B wherein R10 is 2-methylsulfinyl-ethyl- and R3 and R4 are as defined in Table QQ.

Table Q99

Table Q99 provides 18 compounds of formula l-B wherein R10 is 2-methylsulfanyl-ethyl- and R3 and R4 are as defined in Table QQ.

Table Q100

Table Q100 provides 18 compounds of formula l-B wherein R10 is 1-methoxy-prop-2-yl- and R3 and R4 are as defined in Table QQ.

Table Q101

Table Q101 provides 18 compounds of formula l-B wherein R10 is 1-cyanocyclopropyl- and R3 and R4 are as defined in Table QQ.

Table Q 102 Table Q102 provides 18 compounds of formula B wherein R10 is 2-fluoro-ethyl- and R3 and R4 are defined in Table QQ.

Table Q103

Table Q103 provides 18 compounds of formula ^■B wherein R10 is 3-chloroprop-1-yl- and R3 and R4 are as defined in Table QQ.

Table Q 104

Table Q104 provides 18 compounds of formula ^■B wherein R10 is 3,3,3-trifluoro-propyl- and R3 and R4 are as defined in Table QQ.

Table Q105

Table Q105 provides 18 compounds of formula ^■B wherein R10 is 2,2,2-trifluoro-ethyl- and R3 and R4 are as defined in Table QQ.

Table Q106

Table Q106 provides 18 compounds of formula ^■B wherein R10 is 1 ,1 , 1 -trifluoroprop-2-yl- and R3 and R4 are as defined in Table QQ.

Table Q107

Table Q107 provides 18 compounds of formula B wherein R10 is 2,2-difluoro-ethyl- and R3 and R4 as defined in Table QQ.

Table Q108

Table Q108 provides 18 compounds of formula B wherein R10 is methyl- and R3 and R4 are defined in Table QQ.

Table Q109

Table Q109 provides 18 compounds of formula ^■B wherein R10 is ethyl- and R3 and R4 are as defined in Table QQ.

Table Q1 0

Table Q1 0 provides 18 compounds of formula ^■B wherein R10 is prop-1-yl and R3 and R4 are as defined in Table QQ.

Table Q1 1

Table Q1 1 provides 18 compounds of formula ^■B wherein R10 is but-1-yl- and R3 and R4 are as defined in Table QQ.

Table Q1

Table Q1 2 provides 18 compounds of formula B wherein R10 is but-2-yl- and R3 and R4 are defined in Table QQ.

Table Q1

Table Q1 3 provides 18 compounds of formula B wherein R10 is prop-2-yl- and R3 and R4 are defined in Table QQ.

Table Q1

Table Q1 4 provides 18 compounds of formula ^■B wherein R10 is 4-cyanophen-1-yl- and R3 and R4 are as de ined in Table QQ.

Table Q1

Table Q1 5 provides 18 compounds of formula ^■B wherein R10 is (4-chlorophenyl)methyl- and R3 and R4 are as defined in Table QQ.

Table Q1

Table Q1 6 provides 18 compounds of formula ^■B wherein R10 is 2-fluoro-cycloprop-1-yl- and R3 and R4 are as defined in Table QQ.

Table Q1

Table Q1 7 provides 18 compounds of formula ^■B wherein R10 is cyclobutyl- and R3 and R4 are as defined in Table QQ.

Table Q1 8

Table Q1 8 provides 18 compounds of formula ^■B wherein R10 is cyclopropyl- and R3 and R4 are as defined in Table QQ.

Table Q1 9

Table Q1 19 provides 18 compounds of formula B wherein R10 is cyclopentyl- and R3 and R4 are defined in Table QQ.

Table Q120

Table Q120 provides 18 compounds of formula ^■B wherein R10 is (N-methoxypiperid-4-yl)methyl- and R3 and R4 are as defined in Table QQ. Table Q121

Table Q121 provides 18 compounds of formula ^■B wherein R10 is 1-oxo-tetrahydrofuran-3-yl- and R3 and R4 are as defined in Table QQ.

Table Q 122

Table Q122 provides 18 compounds of formula ^■B wherein R10 is 1-oxo-thietan-3-yl- and R3 and R4 are as defined in Table QQ.

Table Q123

Table Q123 provides 18 compounds of formula ^■B wherein R10 is 1 , 1-dioxo-tetrahydrofuran-3-yl- and R3 and R4 are as defined in Table QQ.

Table Q 124

Table Q124 provides 18 compounds of formula ^■B wherein R10 is 1 ,1-dioxo-thietan-3-yl- and R3 and R4 are as defined in Table QQ.

Table Q125

Table Q125 provides 18 compounds of formula ^■B wherein R10 is tetrahydrofuran-2-yl- and R3 and R4 are as defined in Table QQ.

Table Q126

Table Q126 provides 18 compounds of formula ^■B wherein R10 is thietan-3-yl- and R3 and R4 are as defined in Table QQ.

Table Q127

Table Q127 provides 18 compounds of formula ^■B wherein R10 is 3-oxetanyl- and R3 and R4 are as defined in Table QQ.

Table Q128

Table Q128 provides 18 compounds of formula ^■B wherein R10 is tetrahydrofuran-2-yl- and R3 and R4 are as defined in Table QQ.

Table Q129

Table Q129 provides 18 compounds of formula ^■B wherein R10 is tetrahydropyran-4-yl- and R3 and R4 are as defined in Table QQ.

Table Q130

Table Q130 provides 18 compounds of formula ^■B wherein R10 is 2-chloropyrid-4-yl and R3 and R4 are as defined in Table QQ.

Table Q131

Table Q131 provides 18 compounds of formula ^■B wherein R10 is 2-chloropyrid-5-yl- and R3 and R4 are as defined in Table QQ.

Table Q 132

Table Q132 provides 18 compounds of formula ^■B wherein R10 is pyrid-4-yl and R3 and R4 are as defined in Table QQ.

Table Q133

Table Q133 provides 18 compounds of formula ^■B wherein R10 is pyrid-3-yl and R3 and R4 are as defined in Table QQ.

Table Q 134

Table Q134 provides 18 compounds of formula ^■B wherein R10 is 1-oxo-pyrid-4-yl and R3 and R4 are as defined in Table QQ.

Table R

R3 R4 R5 R6a

1 CF3 3,5-dichlorophenyl- Br H

2 CCIF2 3,5-dichlorophenyl- Br H

3 CF3 3,4,5-trichlorophenyl- Br H

4 CCIF2 3,4,5-trichlorophenyl- Br H

5 CF3 3,5-dichloro-4-fluorophenyl- Br H

6 CCIF2 3,5-dichloro-4-fluorophenyl- Br H

7 CF3 3-trifluoromethylphenyl- Br H

8 CCIF2 3-trifluoromethylphenyl- Br H CF3 3,5-bis(trifluoromethyl)phenyl- Br H

CCIF2 3,5-bis(trifluoromethyl)phenyl- Br H

CF3 3-chloro-5-trifluoromethylphenyl- Br H

CCIF2 3-chloro-5-trifluoromethylphenyl- Br H

CF3 3,5-dichlorophenyl- CI H

CCIF2 3,5-dichlorophenyl- CI H

CF3 3,4,5-trichlorophenyl- CI H

CCIF2 3,4,5-trichlorophenyl- CI H

CF3 3,5-dichloro-4-fluorophenyl- CI H

CCIF2 3,5-dichloro-4-fluorophenyl- CI H

CF3 3-trifluoromethylphenyl- CI H

CCIF2 3-trifluoromethylphenyl- CI H

CF3 3 , 5-bis(trif luoromethyl)phenyl- CI H

CCIF2 3,5-bis(trifluoromethyl)phenyl- CI H

CF3 3-chloro-5-trifluoromethylphenyl- CI H

CCIF2 3-chloro-5-trifluoromethylphenyl- CI H

CF3 3,5-dichlorophenyl- CH3 H

CCIF2 3,5-dichlorophenyl- CH3 H

CF3 3,4,5-trichlorophenyl- CH3 H

CCIF2 3,4,5-trichlorophenyl- CH3 H

CF3 3,5-dichloro-4-fluorophenyl- CH3 H

CCIF2 3,5-dichloro-4-fluorophenyl- CH3 H

CF3 3-trifluoromethylphenyl- CH3 H

CCIF2 3-trifluoromethylphenyl- CH3 H

CF3 3,5-bis(trifluoromethyl)phenyl- CH3 H

CCIF2 3,5-bis(trifluoromethyl)phenyl- CH3 H

CF3 3-chloro-5-trifluoromethylphenyl- CH3 H

CCIF2 3-chloro-5-trifluoromethylphenyl- CH3 H

CF3 3,5-dichlorophenyl- CH3CH2 H

CCIF2 3,5-dichlorophenyl- CH3CH2 H

CF3 3,4,5-trichlorophenyl- CH3CH2 H

CCIF2 3,4,5-trichlorophenyl- CH3CH2 H

CF3 3,5-dichloro-4-fluorophenyl- CH3CH2 H

CCIF2 3,5-dichloro-4-fluorophenyl- CH3CH2 H

CF3 3-trifluoromethylphenyl- CH3CH2 H

CCIF2 3-trifluoromethylphenyl- CH3CH2 H

CF3 3,5-bis(trifluoromethyl)phenyl- CH3CH2 H

CCIF2 3,5-bis(trifluoromethyl)phenyl- CH3CH2 H

CF3 3-chloro-5-trifluoromethylphenyl- CH3CH2 H

CCIF2 3-chloro-5-trifluoromethylphenyl- CH3CH2 H

CF3 3,5-dichlorophenyl- Br CH3

CCIF2 3,5-dichlorophenyl- Br CH3

CF3 3,4,5-trichlorophenyl- Br CH3

CCIF2 3,4,5-trichlorophenyl- Br CH3

CF3 3,5-dichloro-4-fluorophenyl- Br CH3

CCIF2 3,5-dichloro-4-fluorophenyl- Br CH3 CF3 3-trifluoromethylphenyl- Br CH3

CCIF2 3-trifluoromethylphenyl- Br CH3

CF3 3,5-bis(trifluoromethyl)phenyl- Br CH3

CCIF2 3,5-bis(trifluoromethyl)phenyl- Br CH3

CF3 3-chloro-5-trifluoromethylphenyl- Br CH3

CCIF2 3-c loro-5-trifluoromethylphenyl- Br CH3

CF3 3,5-dichlorophenyl- CI CH3

CCIF2 3,5-dichlorophenyl- CI CH3

CF3 3,4,5-trichlorophenyl- CI CH3

CCIF2 3,4,5-trichlorophenyl- CI CH3

CF3 3,5-dichloro-4-fluorophenyl- CI CH3

CCIF2 3,5-dichloro-4-fluorophenyl- CI CH3

CF3 3-trifluoromethylphenyl- CI CH3

CCIF2 3-trifluoromethylphenyl- CI CH3

CF3 3,5-bis(trifluoromethyl)phenyl- CI CH3

CCIF2 3,5-bis(trifluoromethyl)phenyl- CI CH3

CF3 3-chloro-5-trifluoromethylphenyl- CI CH3

CCIF2 3-chloro-5-trifluoromethylphenyl- CI CH3

CF3 3,5-dichlorophenyl- CH3 CH3

CCIF2 3,5-dichlorophenyl- CH3 CH3

CF3 3,4,5-trichlorophenyl- CH3 CH3

CCIF2 3,4,5-trichlorophenyl- CH3 CH3

CF3 3,5-dichloro-4-fluorophenyl- CH3 CH3

CCIF2 3,5-dichloro-4-fluorophenyl- CH3 CH3

CF3 3-trifluoromethylphenyl- CH3 CH3

CCIF2 3-trifluoromethylphenyl- CH3 CH3

CF3 3,5-bis(trifluoromethyl)phenyl- CH3 CH3

CCIF2 3,5-bis(trifluoromethyl)phenyl- CH3 CH3

CF3 3-chloro-5-trifluoromethylphenyl- CH3 CH3

CCIF2 3-chloro-5-trifluoromethylphenyl- CH3 CH3

CF3 3,5-dichlorophenyl- CH3CH2 CH3

CCIF2 3,5-dichlorophenyl- CH3CH2 CH3

CF3 3,4,5-trichlorophenyl- CH3CH2 CH3

CCIF2 3,4,5-trichlorophenyl- CH3CH2 CH3

CF3 3,5-dichloro-4-fluorophenyl- CH3CH2 CH3

CCIF2 3,5-dichloro-4-fluorophenyl- CH3CH2 CH3

CF3 3-trifluoromethylphenyl- CH3CH2 CH3

CCIF2 3-trifluoromethylphenyl- CH3CH2 CH3

CF3 3,5-bis(trifluoromethyl)phenyl- CH3CH2 CH3

CCIF2 3,5-bis(trifluoromethyl)phenyl- CH3CH2 CH3

CF3 3-chloro-5-trifluoromethylphenyl- CH3CH2 CH3

CCIF2 3-chloro-5-trifluoromethylphenyl- CH3CH2 CH3

Table R138

Table R138 provides 96 compounds of formula ^■E wherein R8 is 2-methoxy-ethyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R139

Table R139 provides 96 compounds of formula ^■E wherein R8 is 2-(methylsulfonyl)-ethyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R140

Table R140 provides 96 compounds of formula ^■E wherein R8 is 2-methylsulfinyl-ethyl- and R3, R4, R5, and R6a are as defined in Table RR

Table R141

Table R141 provides 96 compounds of formula ^■E wherein R8 is 2-methylsulfanyl-ethyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R142

Table R142 provides 96 compounds of formula ^■E wherein R8 is 1-methoxy-prop-2-yl- and R3, R4, R5, and R6a are as defined in Table RR

Table R143

Table R143 provides 96 compounds of formula ^■E wherein R8 is 1-cyanocyclopropyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R144

Table R144 provides 96 compounds of formula ^■E wherein R8 is 2-fluoro-ethyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R145

Table R145 provides 96 compounds of formula ^■E wherein R8 is 3-chloroprop-1-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R146

Table R146 provides 96 compounds of formula ^■E wherein R8 is 3,3,3-trifluoro-propyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R147

Table R147 provides 96 compounds of formula ^■E wherein R8 is 2,2,2-trifluoro-ethyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R148

Table R148 provides 96 compounds of formula ^■E wherein R8 is 1 ,1 , 1 -trifluoroprop-2-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R149

Table R149 provides 96 compounds of formula ^■E wherein R8 is 2,2-difluoro-ethyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R150

Table R150 provides 96 compounds of formula ^■E wherein R8 is methyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R151

Table R151 provides 96 compounds of formula ^■E wherein R8 is ethyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R152

Table R152 provides 96 compounds of formula ^■E wherein R8 is prop-1-yl and R3, R4, R5, and R6a are as defined in Table RR.

Table R153

Table R153 provides 96 compounds of formula ^■E wherein R8 is but-1-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R154

Table R154 provides 96 compounds of formula l-E wherein R8 is but-2-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R155

Table R155 provides 96 compounds of formula l-E wherein R8 is prop-2-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R156

Table R156 provides 96 compounds of formula l-E wherein R8 is 4-cyanophen-1-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R157

Table R157 provides 96 compounds of formula l-E wherein R8 is (4-chlorophenyl)methyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R158

Table R158 provides 96 compounds of formula l-E wherein R8 is 2-fluoro-cycloprop-1-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R159

Table R159 provides 96 compounds of formula l-E wherein R8 is cyclobutyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R160

Table R160 provides 96 compounds of formula l-E wherein R8 is cyclopropyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R161

Table R161 provides 96 compounds of formula l-E wherein R8 is cyclopentyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R162

Table R162 provides 96 compounds of formula l-E wherein R8 is (N-methoxypiperid-4-yl)methyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R163

Table R163 provides 96 compounds of formula l-E wherein R8 is 1-oxo-tetrahydrofuran-3-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R164

Table R164 provides 96 compounds of formula l-E wherein R8 is 1 -oxo-thietan-3-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R165

Table R165 provides 96 compounds of formula l-E wherein R8 is 1 ,1-dioxo-tetrahydrofuran-3-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R166

Table R166 provides 96 compounds of formula l-E wherein R8 is 1 ,1-dioxo-thietan-3-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R167

Table R167 provides 96 compounds of formula l-E wherein R8 is tetrahydrofuran-2-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R 168

Table R168 provides 96 compounds of formula l-E wherein R8 is thietan-3-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R169

Table R169 provides 96 compounds of formula l-E wherein R8 is 3-oxetanyl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R170

Table R170 provides 96 compounds of formula l-E wherein R8 is tetrahydrofuran-2-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R171

Table R171 provides 96 compounds of formula l-E wherein R8 is tetrahydropyran-4-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R172 Table R172 provides 96 compounds of formula l-E wherein R8 is 2-chloropyrid-4-yl and R3, R4, R5, and R6a are as defined in Table RR.

Table R173

Table R173 provides 96 compounds of formula l-E wherein R8 is 2-chloropyrid-5-yl- and R3, R4, R5, and R6a are as defined in Table RR.

Table R174

Table R174 provides 96 compounds of formula l-E wherein R8 is pyrid-4-yl and R3, R4, R5, and R6a are as defined in Table RR.

Table R175

Table R175 provides 96 compounds of formula l-E wherein R8 is pyrid-3-yl and R3, R4, R5, and R6a are as defined in Table RR.

Table R176

Table R176 provides 96 compounds of formula l-E wherein R8 is 1-oxo-pyrid-4-yl and R3, R4, R5, and R6a are as defined in Table RR.

Compounds of formula I include at least one chiral centre and may exist as compounds of formula 0* or compounds of formula 0**:

0* 0**

Generally compounds of formula 0** are more biologically active than compounds of formula 0*. The invention includes mixtures of compounds 0* and 0** in any ratio e.g. in a molar ratio of 1 :99 to 99: 1 , e.g. 10: 1 to 1 : 10, e.g. a substantially 50:50 molar ratio. In an enantiomerically (or epimerically) enriched mixture of formula 0**, the molar proportion of compound 0** compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%. Likewise, in enantiomerically (or epimerically) enriched mixture of formula 0*, the molar proportion of the compound of formula 0* compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98, or at least 99%. Enantiomerically (or epimerically) enriched mixtures of formula 0** are preferred. Each compound disclosed in Tables 1 to 176 represents a disclosure of a compound according to the compound of formula 0*, and a disclosure according to the compound of formula 0**.

Each compound listed in Tables 1 to 144 represents a specific disclosure corresponding to the compound of formula and a specific disclosure corresponding to the compound of formula *. Compounds of formula I** are more biologically active than compounds of formula I*. The invention includes mixtures of compounds I* and * in any ratio e.g. in a molar ratio of 1 :99 to 99: 1 , e.g. 10: 1 to 1 : 10, e.g. a substantially 50:50 molar ratio. In an enantiomerically (or epimerically) enriched mixture of formula I**, the molar proportion of compound * compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98 or at least 99%.

Enantiomerically (or epimerically) enriched mixtures of formula * are preferred. Each compound disclosed in Tables 1 to 144 represents a specific disclosure of a compound according to formula I*, as well as a specific disclosure of a compound according to formula *.

Likewise compounds of formula I include compounds of formula l*a and l**a

Each compound disclosed in Tables R138 to R176 includes a disclosure of a compound according to the compound of formula l*a, and a disclosure according to the compound of formula l**a.

Likewise compounds of formula I include compounds of formula l*b and l**b

l*b l**b

Each compound disclosed in Tables Q96 to Q134 includes a disclosure of a compound according to the compound of formula l*b, and a disclosure according to the compound of formula l**b.

Likewise, the compound of formula Int-I may exist as a compound of formula Int-I* and Int-I

lnt-1* lnt-1**

The invention includes mixtures of compounds lnt-1* and lnt-1** in any ratio e.g. in a molar ratio of 1 :99 to 99: 1 , e.g. 10:1 to 1 :10, e.g. a substantially 50:50 molar ratio. In an enantiomerically (or epimerically) enriched mixture of formula lnt-l**, the molar proportion of compound lnt-l** compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98 or at least 99%. Enantiomerically (or epimerically) enriched mixtures of formula lnt-l** are preferred.

Likewise, the com ound of formula lnt-ll may exist as a compound of formula lnt-l I* and lnt-l Γ*

The invention includes mixtures of compounds lnt-l I* and lnt-ll** in any ratio e.g. in a molar ratio of 1 :99 to 99: 1 , e.g. 10:1 to 1 :10, e.g. a substantially 50:50 molar ratio. In an enantiomerically (or epimerically) enriched mixture of formula lnt-l I**, the molar proportion of compound lnt-l I** compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98 or at least 99%. Enantiomerically (or epimerically) enriched mixtures of formula lnt-ll** are preferred.

Likewise, the compound of formula Int-lll may exist as a compound of formula Int-lll* and Int-

III**

Int-lll* Int-lll**

The invention includes mixtures of compounds Int-lll* and Int-lll** in any ratio e.g. in a molar ratio of 1 :99 to 99:1 , e.g. 10: 1 to 1 :10, e.g. a substantially 50:50 molar ratio. In an enantiomerically (or epimerically) enriched mixture of formula Int-lll**, the molar proportion of compound Int-lll** compared to the total amount of both enantiomers (or epimers) is for example greater than 50%, e.g. at least 55, 60, 65, 70, 75, 80, 85, 90, 95, 96, 97, 98 or at least 99%. Enantiomerically (or epimerically) enriched mixtures of formula Int-lll** are preferred. The compounds of the invention may be made by a variety of methods as shown in the following Schemes.

Scheme 1

(II)

1 ) Compounds of formula (IA) wherein G is oxygen, can be prepared by reacting a compound of formula (II) wherein G is oxygen and R is OH, d-C₆alkoxy or CI, F or Br, with an amine of formula (III) as shown in Scheme 1. When R is OH such reactions are usually carried out in the presence of a coupling reagent, such as Ν,Ν'-dicyclohexylcarbodiimide ("DCC"), 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride ("EDC") or bis(2-oxo-3-oxazolidinyl)phosphonic chloride ("BOP-CI"), in the presence of a base, and optionally in the presence of a nucleophilic catalyst, such as hydroxybenzotriazole ("HOBT"). When R is CI, such reactions are usually carried out in the presence of a base, and optionally in the presence of a nucleophilic catalyst. Alternatively, it is possible to conduct the reaction in a biphasic system comprising an organic solvent, preferably ethyl acetate, and an aqueous solvent, preferably a solution of sodium hydrogen carbonate. When R is d-C₆alkoxy it is sometimes possible to convert the ester directly to the amide by heating the ester and amine together in a thermal process. Suitable bases include pyridine, triethylamine, 4-(dimethylamino)-pyridine ("DMAP") or diisopropylethylamine (Hunig's base). Preferred solvents are A/,A/-dimethylacetamide, tetrahydrofuran, dioxane, 1 ,2-dimethoxyethane, ethyl acetate and toluene. The reaction is carried out at a temperature of from 0°C to 100°C, preferably from 15°C to 30°C, in particular at ambient temperature. Amines of formula (III) are either known in the literature or can be prepared using methods known to a person skilled in the art. Some of these methods are described in the preparation Examples.

2) Acid halides of formula (II), wherein G is oxygen and R is CI, F or Br, may be made from carboxylic acids of formula (II), wherein G is oxygen and R is OH, under standard conditions, as described for example in WO2009/080250.

3) Carboxylic acids of formula (II), wherein G is oxygen and R is OH, may be formed from esters of formula (II), wherein G is oxygen and R is d-C₆alkoxy as described for example in scheme 3.

4) Compounds of formula (IA), wherein G is sulfur, may be made by treatment of a compound of formula (II), wherein G is oxygen and R is OH, d-C₆alkoxy or CI, F or Br, with a thio-transfer reagent such as Lawesson's reagent or phosphorus pentasulfide prior to elaborating to compounds of formula (I), as described under 1 ). Scheme 2

(IA)

5) Alternatively, compounds of formula (IA) wherein G is oxygen, can be prepared by various methods from an intermediate of formula (IV) as shown in Scheme 2 wherein G is oxygen and X^B is a leaving group, for example a halogen, such as bromo or X^B is cyano, formyl, acid, amide or acetyl according to similar methods to those described in scheme 3. An intermediate of formula (IV) can be prepared for example from an intermediate of formula (V) as described in Scheme 1 ).

Scheme 3

H

In scheme 3 and following schemes, A¹, A², A³, A⁴ are as defined for the compound of formula I, and Ar stands for group Ar1 or group Ar2 or group Ar3 or group Ar4 or group Ar5, wherein R is d- C₆alkyl or Ci-C₆alkyl optionally substituted by aryl and X^c is a leaving group for example a halogen, d- C₈alkoxy, Ci-C₈alkylsulfonyloxy, Ci-C₈haloalkylsulfonyloxy, Ci-C₈arylsulfonyloxy, optionally substituted Ci-C₈arylsulfonyloxy (aryl is preferably phenyl), diazonium salts (e.g. -N₂ ⁺ CI^", -N₂ ⁺ BF₄ ^", -N₂ ⁺ Br^", -N₂ ⁺ PF₆ phosphonate esters (e.g. -OP(0)(OR)_2, wherein R is methyl or ethyl), preferably bromo, iodo, chloro, trifluorometh lsulfoxy, p-toluenesulfoxy, diazonium chloride.

(Ar1 ) (Ar2) (Ar3) (Ar4) (Ar5)

6) Compounds of formula (IG) can be prepared by reacting compounds of formula (IIG) with reagents such as Ν,Ν-dimethyldialkylacetal in a suitable solvent such as dimethylsulfoxide, N, N- dimethylformamide, or N-methylpyrrolidinone. The reaction is carried out at a temperature of from 25 °C to 160 °C.

7) Compounds of formula (IIG) can be prepared from compounds of formula (IIIG), wherein R³⁰ is Ci-Ci₅alkyl by hydrolysis of the ester moiety. For example, in the case where R³⁰ is methyl or ethyl, the hydrolysis can be done with water and a base, such as potassium hydroxide, in the absence or in the presence of a solvent, such as, for instance, tetrahydrofuran, dioxane or methanol. In the case where R³⁰ is, for example, ieri-butyl, the hydrolysis can be done in the presence of acid, such as trifluoroacetic acid or hydrochloric acid. The reaction is carried out at a temperature of from -120°C to +130°C, preferably from -100°C to 100°C.

8) Alternatively compounds of formula (IG) can be prepared by reacting compounds of formula

(VG) with silver salts such as silver carbonate or silver oxide in a suitable solvent such as

dimethylsulfoxide, N, N-dimethylformamide, or N-methylpyrrolidinone. The reaction is carried out at a temperature of from 25 °C to 160 °C.

9) Compounds of formula (VG) can be prepared from compounds of formula (IIIG) by a two-step procedure. Compounds of formula (IIIG) can be converted to compounds of formula (VIG) by dehydration using reagents such as thionyl chloride, phosphorus trichloride or methanesulfonylchloride in the presence of organic bases such as triethylamine, pyridine or di-isopropylamine. Compounds of formula (VIG) can then be converted to compound of formula (VG) as described in 2).

10) Compounds of formula (IIIG) can be prepared by reacting chalcones of formula (IVG) with alkylthioglycolates of formula (VUG), wherein R³⁰ is d-Ci₅alkyl in presence of organic bases such as triethyl amine, pyridine, diisopropylamine, piperidine, or inorganic bases such as alkaline salts, such as carbonates and hydroxides, in a suitable solvent such as tetrahydrofuran,, dioxane or toluene. The reaction is carried out at a temperature of from 0 °C to 100 °C. (See Tetrahedron Lett. 1964, (23-4), 1609) Scheme 4

1 1 ) Compounds of formula (IA) and (II)

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 compounsd of the invention include those pests associated with agriculture (which term includes the growing of crops for food and fiber 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). The compounds of the invention may be used for example on turf, ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers, as well as for tree injection, pest management and the like. Compositions comprising the compound of formula I may be used on ornamental garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), e.g. to control aphids, whitefly, scales, meelybug, beetles and caterpillars. Compositions comprising the compound of formula I may be used on garden plants (e.g. flowers, shrubs, broad-leaved trees or evergreens), on indoor plants (e.g. flowers and shrubs) and on indoor pest e.g. to control aphids, whitefly, scales, meelybug, beetles and caterpillars.

Furthermore, the compounds of the invention may be effective against harmful insects, without substantially imposing any harmful side effects to cultivated plants. Application of the compounds of the invention may increase the harvest yields, and may improve the quality of the harvested material. The compounds of the invention may have favourable properties with respect to amount appled, residue formulation, selectivity, toxicity, production methodology, high activity, wide spectrum of control, safety, control of resistant organisms, e.g. pests that are resistant to organic phosphorus agents and/or carbamate agents. _g7

The activity of compositions comprising compounds according to the invention can be broadened considerably, and adapted to prevailing circumstances, by including other active substances. The active substances can be of chemical or biological in type, and in the case of biological could be further modified from the biological species derived in nature. Active substances include substances that control, repel or attract pests that damage or harm useful plants in general, but also substances that improve the growth of a useful plant, such as plant growth regulators, and substances that improve the performance of the active substance, such as synergists. Examples are insecticides, acaricides, nematicides, molluscicides, aligicides, virusicides, rodenticide, bactericides, fungicides, chemosterilants, anthelmintics. Examples of a biological active substance include baculovirus, plant extract, and bacteria.

The mixtures of the compounds of formula I with other active substances may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity. For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled in their different development stages, or better behaviour relating to production, for example grinding or mixing, storage or use.

Individual active substances can occur in more than one group or class, and at more than one place within a group or class: information about the active substances, their spectrum, sources and classifications can be found from Compendium of Pesticide Common Names (see

http://www.alanwood.net/pesticides/index.html) or from the Pesticide Manual created by the British Crop Production Counci (see http://bcpcdata.com/pesticide-manual.html).

Preferred mixtures are indicated below where a compound of formula I according to the invention is indicated as "I".

Compositions comprising an adjuvant include I + compounds selected from the group of substances consisting of petroleum oils;

Compositions comprising an acaricide include I + 1 , 1-bis(4-chlorophenyl)-2-ethoxyethanol, I + 2,4-dichlorophenyl benzenesulfonate, I + 2-fluoro-A/-methyl-A/-1-naphthylacetamide, I + 4-chlorophenyl phenyl sulfone, I + abamectin, I + acequinocyl, I + acetoprole, I + acrinathrin, I + aldicarb, I + aldoxycarb, I + alpha-cypermethrin, I + amidithion, I + amidoflumet, I + amidothioate, I + amiton, I + amiton hydrogen oxalate, I + amitraz, I + aramite, I + arsenous oxide, I + AVI 382, I + AZ 60541 , I + azinphos-ethyl, I + azinphos-methyl, I + azobenzene, I + azocyclotin, I + azothoate, I + benomyl, I + benoxafos, I + benzoximate, I + benzyl benzoate, I + bifenazate, I + bifenthrin, I + binapacryl, I + brofenvalerate, I + bromocyclen, I + bromophos, I + bromophos-ethyl, I + bromopropylate, I + buprofezin, I + butocarboxim, I + butoxycarboxim, I + butylpyridaben, I + calcium polysulfide, I + camphechlor, I + carbanolate, I + carbaryl, I + carbofuran, I + carbophenothion, I + CGA 50'439, I + chinomethionat, I + chlorbenside, I + chlordimeform, I + chlordimeform hydrochloride, I + chlorfenapyr, I + chlorfenethol, I + chlorfenson, I + chlorfensulfide, I + chlorfenvinphos, I + chlorobenzilate, I + chloromebuform, I + chloromethiuron, I + chloropropylate, I + chlorpyrifos, I + chlorpyrifos-methyl, I + chlorthiophos, I + cinerin I, I + cinerin II, I + cinerins, I + clofentezine, I + closantel, I + coumaphos, I + crotamiton, I + crotoxyphos, I + cufraneb, I + cyanthoate, I + cyflumetofen, I + cyhalothrin, I + cyhexatin, I + cypermethrin, I + DCPM, I + DDT, I + demephion, I + demephion-O, I + demephion-S, I + demeton, I + demeton-methyl, I + demeton-O, I + demeton-O-methyl, I + demeton-S, I + demeton-S-methyl, I + demeton-S-methylsulfon, I + diafenthiuron, I + dialifos, I + diazinon, I + dichlofluanid, I + dichlorvos, I + dicliphos, I + dicofol, I + dicrotophos, I + dienochlor, I + dimefox, I + dimethoate, I + dinactin , I + dinex, I + dinex-diclexine, I + dinobuton, I + „„

-68- dinocap, I + dinocap-4, I + dinocap-6, I + dinocton, I + dinopenton, I + dinosulfon, I + dinoterbon, I + dioxathion, I + diphenyl sulfone, I + disulfiram, I + disulfoton, I + DNOC, I + dofenapyn, I + doramectin, I + endosulfan, I + endothion, I + EPN, I + eprinomectin, I + ethion, I + ethoate-methyl, I + etoxazole, I + etrimfos, I + fenazaflor, I + fenazaquin, I + fenbutatin oxide, I + fenothiocarb, I + fenpropathrin, I + fenpyrad, I + fenpyroximate, I + fenson, I + fentrifanil, I + fenvalerate, I + fipronil, I + fluacrypyrim, I + fluazuron, I + flubenzimine, I + flucycloxuron, I + flucythrinate, I + fluenetil, I + flufenoxuron, I + flumethrin, I + fluorbenside, I + fluvalinate, I + FMC 1 137, I + formetanate, I + formetanate hydrochloride, I + formothion, I + formparanate, I + gamma-HCH, I + glyodin, I + halfenprox, I + heptenophos, I + hexadecyl cyclopropanecarboxylate, I + hexythiazox, I + iodomethane, I + isocarbophos, I + isopropyl 0- (methoxyaminothiophosphoryl)salicylate, I + ivermectin, I + jasmolin I, I + jasmolin II, I + jodfenphos, I + lindane, I + lufenuron, I + malathion, I + malonoben, I + mecarbam, I + mephosfolan, I + mesulfen, I + methacrifos, I + methamidophos, I + methidathion, I + methiocarb, I + methomyl, I + methyl bromide, I + metolcarb, I + mevinphos, I + mexacarbate, I + milbemectin, I + milbemycin oxime, I + mipafox, I + monocrotophos, I + morphothion, I + moxidectin, I + naled, I + NC-184, I + NC-512, I + nifluridide, I + nikkomycins, I + nitrilacarb, I + nitrilacarb 1 : 1 zinc chloride complex, I + NNI-0101 , I + NNI-0250, I + omethoate, I + oxamyl, I + oxydeprofos, I + oxydisulfoton, I + pp'-DDT, I + parathion, I + permethrin, I + petroleum oils, I + phenkapton, I + phenthoate, I + phorate, I + phosalone, I + phosfolan, I + phosmet, I + phosphamidon, I + phoxim, I + pirimiphos-methyl, I + polychloroterpenes, I + polynactins, I + proclonol, I + profenofos, I + promacyl, I + propargite, I + propetamphos, I + propoxur, I + prothidathion, I + prothoate, I + pyrethrin I, I + pyrethrin II, I + pyrethrins, I + pyridaben, I + pyridaphenthion, I + pyrimidifen, I + pyrimitate, I + quinalphos, I + quintiofos, I + R-1492, I + RA-17, I + rotenone, I + schradan, I + sebufos, I + selamectin, I + SI-0009, I + sophamide, I + spirodiclofen, I + spiromesifen, I + SSI-121 , I + sulfiram, I + sulfluramid, I + sulfotep, I + sulfur, I + SZI-121 , I + tau-fluvalinate, I + tebufenpyrad, I + TEPP, I + terbam, I + tetrachlorvinphos, I + tetradifon, I + tetranactin, I + tetrasul, I + thiafenox, I + thiocarboxime, I + thiofanox, I + thiometon, I + thioquinox, I + thuringiensin, I + triamiphos, I + triarathene, I + triazophos, I + triazuron, I + trichlorfon, I + trifenofos, I + trinactin, I + vamidothion, I + vaniliprole and I + YI-5302;

Compositions comprising an anthelmintic include I + abamectin, I + crufomate, I + doramectin, I + emamectin, I + emamectin benzoate, I + eprinomectin, I + ivermectin, I + milbemycin oxime, I + moxidectin, I + piperazine, I + selamectin, I + spinosad and I + thiophanate;

Compositions comprising an avicide include I + chloralose, I + endrin, I + fenthion, I + pyridine- amine and I + strychnine;

Compositions comprising a biological control agent include I + Adoxophyes orana GV, I + Agrobacterium radiobacter, I + Amblyseius spp., I + Anagrapha falcifera NPV, I + Anagrus atomus, I + Aphelinus abdominalis, I + Aphidius colemani, I + Aphidoletes aphidimyza, I + Autographa californica NPV, I + Bacillus firmus, I + Bacillus sphaericus Neide, I + Bacillus thuringiensis Berliner, I + Bacillus thuringiensis subsp. aizawai, I + Bacillus thuringiensis subsp. israelensis, I + Bacillus thuringiensis subsp. japonensis, I + Bacillus thuringiensis subsp. kurstaki, I + Bacillus thuringiensis subsp. tenebrionis, I + Beauveria bassiana, I + Beauveria brongniartii, I + Chrysoperla carnea, I + Cryptolaemus montrouzieri, I + Cydia pomonella GV, I + Dacnusa sibirica, I + Diglyphus isaea, I + Encarsia formosa, I + Eretmocerus eremicus, I + Helicoverpa zea NPV, I + Heterorhabditis bacteriophora and H. megidis, I + Hippodamia convergens, I + Leptomastix dactylopii, I + Macrolophus caliginosus, I + Mamestra brassicae NPV, I + _

-69-

Metaphycus helvolus, I + Metarhizium anisopliae var. acridum, I + Metarhizium anisopliae var. anisopliae, I + Neodiprion sertifer NPV and N. lecontei NPV, I + Orius spp., I + Paecilomyces fumosoroseus, I + Phytoseiulus persimilis, I + Spodoptera exigua multicapsid nuclear polyhedrosis virus, I + Steinemema bibionis, I + Steinemema carpocapsae, I + Steinemema feltiae, I + Steinemema glaseri, I + Steinemema riobrave, I + Steinemema riobravis, I + Steinemema scapterisci, I + Steinemema spp., I + Trichogramma spp., I + Typhlodromus occidentalis and I + Verticillium lecanii;

Compositions comprising a soil sterilant include I + iodomethane and methyl bromide;

Compositions comprising a chemosterilant include I + apholate, I + bisazir, I + busulfan, I + diflubenzuron, I + dimatif, I + hemel, I + hempa, I + metepa, I + methiotepa, I + methyl apholate, I + morzid, I + penfluron, I + tepa, I + thiohempa, I + thiotepa, I + tretamine and I + uredepa;

Compositions comprising an insect pheromone include I + (E)-dec-5-en-1-yl acetate with (E)-dec- 5-en-1-ol, I + (E)-tridec-4-en-1-yl acetate, I + (E)-6-methylhept-2-en-4-ol, I + (E,Z)-tetradeca-4, 10-dien-1- yl acetate, I + (Z)-dodec-7-en-1-yl acetate, I + (Z)-hexadec-l 1-enal, I + (Z)-hexadec-l 1-en-1-yl acetate, I + (Z)-hexadec-13-en-1 1-yn-1-yl acetate, I + (Z)-icos-13-en-10-one, I + (Z)-tetradec-7-en-1-al, I + (Z)- tetradec-9-en-1-ol, I + (Z)-tetradec-9-en-1-yl acetate, I + (7E,9Z)-dodeca-7,9-dien-1-yl acetate, I + (9Z, 1 1 E)-tetradeca-9, 1 1-dien-1-yl acetate, I + (9Z, 12E)-tetradeca-9, 12-dien-1-yl acetate, I + 14- methyloctadec-1-ene, I + 4-methylnonan-5-ol with 4-methylnonan-5-one, I + alpha-multistriatin, I + brevicomin, I + codlelure, I + codlemone, I + cuelure, I + disparlure, I + dodec-8-en-1-yl acetate, I + dodec-9-en-1-yl acetate, I + dodeca-8, I + 10-dien-1-yl acetate, I + dominicalure, I + ethyl 4- methyloctanoate, I + eugenol, I + frontalin, I + gossyplure, I + grandlure, I + grandlure I, I + grandlure II, I + grandlure III, I + grandlure IV, I + hexalure, I + ipsdienol, I + ipsenol, I + japonilure, I + lineatin, I + litlure, I + looplure, I + medlure, I + megatomoic acid, I + methyl eugenol, I + muscalure, I + octadeca-2, 13-dien- 1-yl acetate, I + octadeca-3, 13-dien-1-yl acetate, I + orfralure, I + oryctalure, I + ostramone, I + siglure, I + sordidin, I + sulcatol, I + tetradec-1 1-en-1-yl acetate, I + trimedlure, I + trimedlure A, I + trimedlure Β-ι , I + trimedlure B₂, I + trimedlure C and I + trunc-call;

Compositions comprising an insect repellent include I + 2-(octylthio)ethanol, I + butopyronoxyl, I + butoxy(polypropylene glycol), I + dibutyl adipate, I + dibutyl phthalate, I + dibutyl succinate, I + diethyltoluamide, I + dimethyl carbate, I + dimethyl phthalate, I + ethyl hexanediol, I + hexamide, I + methoquin-butyl, I + methylneodecanamide, I + oxamate and I + picaridin;

Compositions comprising an insecticide include I + 1-dichloro-1-nitroethane, I + 1 , 1-dichloro-2,2- bis(4-ethylphenyl)ethane , I +, I + 1 ,2-dichloropropane, I + 1 ,2-dichloropropane with 1 ,3-dichloropropene, I + 1-bromo-2-chloroethane, I + 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate, I + 2,2-dichlorovinyl 2- ethylsulfinylethyl methyl phosphate, I + 2-(1 ,3-dithiolan-2-yl)phenyl dimethylcarbamate, I + 2-(2- butoxyethoxy)ethyl thiocyanate, I + 2-(4,5-dimethyl-1 ,3-dioxolan-2-yl)phenyl methylcarbamate, I + 2-(4- chloro-3,5-xylyloxy)ethanol, I + 2-chlorovinyl diethyl phosphate, I + 2-imidazolidone, I + 2-isovalerylindan- 1 ,3-dione, I + 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate, I + 2-thiocyanatoethyl laurate, I + 3- bromo-1-chloroprop-1-ene, I + 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate, I + 4-methyl(prop-2- ynyl)amino-3,5-xylyl methylcarbamate, I + 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate, I + abamectin, I + acephate, I + acetamiprid, I + acethion, I + acetoprole, I + acrinathrin, I + acrylonitrile, I + alanycarb, I + aldicarb, I + aldoxycarb, I + aldrin, I + allethrin, I + allosamidin, I + allyxycarb, I + alpha- cypermethrin, I + alpha-ecdysone, I + aluminium phosphide, I + amidithion, I + amidothioate, I + _7Q aminocarb, I + amiton, I + amiton hydrogen oxalate, I + amitraz, I + anabasine, I + athidathion, I + AVI 382, I + AZ 60541 , I + azadirachtin, I + azamethiphos, I + azinphos-ethyl, I + azinphos-methyl, I + azothoate, I + Bacillus thuringiensis delta endotoxins, I + barium hexafluorosilicate, I + barium polysulfide, I + barthrin, I + Bayer 22/190, I + Bayer 22408, I + bendiocarb, I + benfuracarb, I + bensultap, I + beta- cyfluthrin, I + beta-cypermethrin, I + bifenthrin, I + bioallethrin, I + bioallethrin S-cyclopentenyl isomer, I + bioethanomethrin, I + biopermethrin, I + bioresmethrin, I + bis(2-chloroethyl) ether, I + bistrifluron, I + borax, I + brofenvalerate, I + bromfenvinfos, I + bromocyclen, I + bromo-DDT, I + bromophos, I + bromophos-ethyl, I + bufencarb, I + buprofezin, I + butacarb, I + butathiofos, I + butocarboxim, I + butonate, I + butoxycarboxim, I + butylpyridaben, I + cadusafos, I + calcium arsenate, I + calcium cyanide, I + calcium polysulfide, I + camphechlor, I + carbanolate, I + carbaryl, I + carbofuran, I + carbon disulfide, I + carbon tetrachloride, I + carbophenothion, I + carbosulfan, I + cartap, I + cartap

hydrochloride, I + cevadine, I + chlorbicyclen, I + chlordane, I + chlordecone, I + chlordimeform, I + chlordimeform hydrochloride, I + chlorethoxyfos, I + chlorfenapyr, I + chlorfenvinphos, I + chlorfluazuron, I + chlormephos, I + chloroform, I + chloropicrin, I + chlorphoxim, I + chlorprazophos, I + chlorpyrifos, I + chlorpyrifos-methyl, I + chlorthiophos, I + chromafenozide, I + cinerin I, I + cinerin II, I + cinerins, I + cis- resmethrin, I + cismethrin, I + clocythrin, I + cloethocarb, I + closantel, I + clothianidin, I + copper acetoarsenite, I + copper arsenate, I + copper oleate, I + coumaphos, I + coumithoate, I + crotamiton, I + crotoxyphos, I + crufomate, I + cryolite, I + CS 708, I + cyanofenphos, I + cyanophos, I + cyanthoate, I + cyclethrin, I + cycloprothrin, I + cyfluthrin, I + cyhalothrin, I + cypermethrin, I + cyphenothrin, I + cyromazine, I + cythioate, I + cf-limonene, I + cf-tetramethrin, I + DAEP, I + dazomet, I + DDT, I + decarbofuran, I + deltamethrin, I + demephion, I + demephion-O, I + demephion-S, I + demeton, I + demeton-methyl, I + demeton-O, I + demeton-O-methyl, I + demeton-S, I + demeton-S-methyl, I + demeton-S-methylsulphon, I + diafenthiuron, I + dialifos, I + diamidafos, I + diazinon, I + dicapthon, I + dichlofenthion, I + dichlorvos, I + dicliphos, I + dicresyl, I + dicrotophos, I + dicyclanil, I + dieldrin, I + diethyl 5-methylpyrazol-3-yl phosphate, I + diflubenzuron, I + dilor, I + dimefluthrin, I + dimefox, I + dimetan, I + dimethoate, I + dimethrin, I + dimethylvinphos, I + dimetilan, I + dinex, I + dinex-diclexine, I + dinoprop, I + dinosam, I + dinoseb, I + dinotefuran, I + diofenolan, I + dioxabenzofos, I + dioxacarb, I + dioxathion, I + disulfoton, I + dithicrofos, I + DNOC, I + doramectin, I + DSP, I + ecdysterone, I + El 1642, I + emamectin, I + emamectin benzoate, I + EMPC, I + empenthrin, I + endosulfan, I + endothion, I + endrin, I + EPBP, I + EPN, I + epofenonane, I + eprinomectin, I + esfenvalerate, I + etaphos, I + ethiofencarb, I + ethion, I + ethiprole, I + ethoate-methyl, I + ethoprophos, I + ethyl formate, I + ethyl-DDD, I + ethylene dibromide, I + ethylene dichloride, I + ethylene oxide, I + etofenprox, I + etrimfos, I + EXD, I + famphur, I + fenamiphos, I + fenazaflor, I + fenchlorphos, I + fenethacarb, I + fenfluthrin, I + fenitrothion, I + fenobucarb, I + fenoxacrim, I + fenoxycarb, I + fenpirithrin, I + fenpropathrin, I + fenpyrad, I + fensulfothion, I + fenthion, I + fenthion-ethyl, I + fenvalerate, I + fipronil, I + flonicamid, I + flubendiamide, I + flucofuron, I + flucycloxuron, I + flucythrinate, I + fluenetil, I + flufenerim, I + flufenoxuron, I + flufenprox, I + flumethrin, I + fluvalinate, I + FMC 1 137, I + fonofos, I + formetanate, I + formetanate hydrochloride, I + formothion, I + formparanate, I + fosmethilan, I + fospirate, I + fosthiazate, I + fosthietan, I +

furathiocarb, I + furethrin, I + gamma-cyhalothrin, I + gamma-HCH, I + guazatine, I + guazatine acetates, I + GY-81 , I + halfenprox, I + halofenozide, I + HCH, I + HEOD, I + heptachlor, I + heptenophos, I + heterophos, I + hexaflumuron, I + HHDN, I + hydramethylnon, I + hydrogen cyanide, I + hydroprene, I + hyquincarb, I + imidacloprid, I + imiprothrin, I + indoxacarb, I + iodomethane, I + IPSP, I + isazofos, I + isobenzan, I + isocarbophos, I + isodrin, I + isofenphos, I + isolane, I + isoprocarb, I + isopropyl 0- (methoxyaminothiophosphoryl)salicylate, I + isoprothiolane, I + isothioate, I + isoxathion, I + ivermectin, I + jasmolin I, I + jasmolin II, I + jodfenphos, I + juvenile hormone I, I + juvenile hormone II, I + juvenile hormone III, I + kelevan, I + kinoprene, I + lambda-cyhalothrin, I + lead arsenate, I + lepimectin, I + leptophos, I + lindane, I + lirimfos, I + lufenuron, I + lythidathion, I + m-cumenyl methylcarbamate, I + magnesium phosphide, I + malathion, I + malonoben, I + mazidox, I + mecarbam, I + mecarphon, I + menazon, I + mephosfolan, I + mercurous chloride, I + mesulfenfos, I + metaflumizone, I + metam, I + metam-potassium, I + metam-sodium, I + methacrifos, I + methamidophos, I + methanesulfonyl fluoride, I + methidathion, I + methiocarb, I + methocrotophos, I + methomyl, I + methoprene, I + methoquin-butyl, I + methothrin, I + methoxychlor, I + methoxyfenozide, I + methyl bromide, I + methyl isothiocyanate, I + methylchloroform, I + methylene chloride, I + metofluthrin, I + metolcarb, I + metoxadiazone, I + mevinphos, I + mexacarbate, I + milbemectin, I + milbemycin oxime, I + mipafox, I + mirex, I + monocrotophos, I + morphothion, I + moxidectin, I + naftalofos, I + naled, I + naphthalene, I + NC-170, I + NC-184, I + nicotine, I + nicotine sulfate, I + nifluridide, I + nitenpyram, I + nithiazine, I + nitrilacarb, I + nitrilacarb 1 : 1 zinc chloride complex, I + NNI-0101 , I + NNI-0250, I + nornicotine, I + novaluron, I + noviflumuron, I + 0-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, I + 0,0-diethyl 0-4-methyl-2- oxo-2/-/-chromen-7-yl phosphorothioate, I + Ο,Ο-diethyl 0-6-methyl-2-propylpyrimidin-4-yl

phosphorothioate, I + Ο,Ο,Ο', O'-tetrapropyl dithiopyrophosphate, I + oleic acid, I + omethoate, I + oxamyl, I + oxydemeton-methyl, I + oxydeprofos, I + oxydisulfoton, I + pp'-DDT, I + para-dichlorobenzene, I + parathion, I + parathion-methyl, I + penfluron, I + pentachlorophenol, I + pentachlorophenyl laurate, I + permethrin, I + petroleum oils, I + PH 60-38, I + phenkapton, I + phenothrin, I + phenthoate, I + phorate+ TX, I + phosalone, I + phosfolan, I + phosmet, I + phosnichlor, I + phosphamidon, I + phosphine, I + phoxim, I + phoxim-methyl, I + pirimetaphos, I + pirimicarb, I + pirimiphos-ethyl, I + pirimiphos-methyl, I + polychlorodicyclopentadiene isomers, I + polychloroterpenes, I + potassium arsenite, I + potassium thiocyanate, I + prallethrin, I + precocene I, I + precocene II, I + precocene III, I + primidophos, I + profenofos, I + profluthrin, I + promacyl, I + promecarb, I + propaphos, I + propetamphos, I + propoxur, I + prothidathion, I + prothiofos, I + prothoate, I + protrifenbute, I + pymetrozine, I + pyraclofos, I + pyrazophos, I + pyresmethrin, I + pyrethrin I, I + pyrethrin II, I + pyrethrins, I + pyridaben, I + pyridalyl, I + pyridaphenthion, I + pyrimidifen, I + pyrimitate, I + pyriproxyfen, I + quassia, I + quinalphos, I + quinalphos-methyl, I + quinothion, I + quintiofos, I + R-1492, I + rafoxanide, I + resmethrin, I + rotenone, I + RU 15525, I + RU 25475, I + ryania, I + ryanodine, I + sabadilla, I + schradan, I + sebufos, I + selamectin, I + SI-0009, I + SI-0205, I + SI-0404, I + SI-0405, I + silafluofen, I + SN 72129, I + sodium arsenite, I + sodium cyanide, I + sodium fluoride, I + sodium hexafluorosilicate, I + sodium

pentachlorophenoxide, I + sodium selenate, I + sodium thiocyanate, I + sophamide, I + spinosad, I + spiromesifen, I + spirotetrmat, I + sulcofuron, I + sulcofuron-sodium, I + sulfluramid, I + sulfotep, I + sulfuryl fluoride, I + sulprofos, I + tar oils, I + tau-fluvalinate, I + tazimcarb, I + TDE, I + tebufenozide, I + tebufenpyrad, I + tebupirimfos, I + teflubenzuron, I + tefluthrin, I + temephos, I + TEPP, I + terallethrin, I + terbam, I + terbufos, I + tetrachloroethane, I + tetrachlorvinphos, I + tetramethrin, I + theta-cypermethrin, I + thiacloprid, I + thiafenox, I + thiamethoxam, I + thicrofos, I + thiocarboxime, I + thiocyclam, I + thiocyclam hydrogen oxalate, I + thiodicarb, I + thiofanox, I + thiometon, I + thionazin, I + thiosultap, I + thiosultap-sodium, I + thuringiensin, I + tolfenpyrad, I + tralomethrin, I + transfluthrin, I + transpermethrin, I + triamiphos, I + triazamate, I + triazophos, I + triazuron, I + trichlorfon, I + trichlormetaphos-3, I + trichloronat, I + trifenofos, I + triflumuron, I + trimethacarb, I + triprene, I + vamidothion, I + vaniliprole, I + veratridine, I + veratrine, I + XMC, I + xylylcarb, I + YI-5302, I + zeta-cypermethrin, I + zetamethrin, I + zinc phosphide, I + zolaprofos and ZXI 8901 , I + cyantraniliprole, I + chlorantraniliprole, I + cyenopyrafen, I + cyflumetofen, I + pyrifluquinazon, I + spinetoram, I + spirotetramat, I + sulfoxaflor, I + flufiprole, I + meperfluthrin, I + tetramethylfluthrin, I + triflumezopyrim;

Compositions comprising a molluscicide include I + bis(tributyltin) oxide, I + bromoacetamide, I + calcium arsenate, I + cloethocarb, I + copper acetoarsenite, I + copper sulfate, I + fentin, I + ferric phosphate, I + metaldehyde, I + methiocarb, I + niclosamide, I + niclosamide-olamine, I +

pentachlorophenol, I + sodium pentachlorophenoxide, I + tazimcarb, I + thiodicarb, I + tributyltin oxide, I + trifenmorph, I + trimethacarb, I + triphenyltin acetate and triphenyltin hydroxide, I + pyriprole;

Compositions comprising a nematicide include 1+ AKD-3088, I + 1 ,2-dibromo-3-chloropropane, I + 1 ,2-dichloropropane, I + 1 ,2-dichloropropane with 1 ,3-dichloropropene, I + 1 ,3-dichloropropene, I + 3,4- dichlorotetrahydrothiophene 1 ,1-dioxide, I + 3-(4-chlorophenyl)-5-methylrhodanine, I + 5-methyl-6-thioxo- 1 ,3,5-thiadiazinan-3-ylacetic acid, I + 6-isopentenylaminopurine, I + abamectin, I + acetoprole, I + alanycarb, I + aldicarb, I + aldoxycarb, I + AZ 60541 , I + benclothiaz, I + benomyl, I + butylpyridaben, I + cadusafos, I + carbofuran, I + carbon disulfide, I + carbosulfan, I + chloropicrin, I + chlorpyrifos, I + cloethocarb, I + cytokinins, I + dazomet, I + DBCP, I + DCIP, I + diamidafos, I + dichlofenthion, I + dicliphos, I + dimethoate, I + doramectin, I + emamectin, I + emamectin benzoate, I + eprinomectin, I + ethoprophos, I + ethylene dibromide, I + fenamiphos, I + fenpyrad, I + fensulfothion, I + fosthiazate, I + fosthietan, I + furfural, I + GY-81 , I + heterophos, I + iodomethane, I + isamidofos, I + isazofos, I + ivermectin, I + kinetin, I + mecarphon, I + metam, I + metam-potassium, I + metam-sodium, I + methyl bromide, I + methyl isothiocyanate, I + milbemycin oxime, I + moxidectin, I + Myrothecium verrucaria composition, I + NC-184, I + oxamyl, I + phorate, I + phosphamidon, I + phosphocarb, I + sebufos, I + selamectin, I + spinosad, I + terbam, I + terbufos, I + tetrachlorothiophene, I + thiafenox, I + thionazin, I + triazophos, I + triazuron, I + xylenols, I + YI-5302 and zeatin, I + fluensulfone;

Compositions comprising a synergist include I + 2-(2-butoxyethoxy)ethyl piperonylate, I + 5-(1 ,3- benzodioxol-5-yl)-3-hexylcyclohex-2-enone, I + farnesol with nerolidol, I + MB-599, I + MGK 264, I + piperonyl butoxide, I + piprotal, I + propyl isomer, I + S421 , I + sesamex, I + sesasmolin and I + sulfoxide;

Compositions comprising an animal repellent include l+ anthraquinone, I + chloralose, I + copper naphthenate, I + copper oxychloride, I + diazinon, I + dicyclopentadiene, I + guazatine, I + guazatine acetates, I + methiocarb, I + pyridin-4-amine, I + thiram, I + trimethacarb, I + zinc naphthenate and I + ziram;

Further compositions include I + Brofluthrinate, I + Cycloxaprid, I + Diflovidazine, I + Flometoquin,

I + Fluhexafon, I + Guadipyr, I + Plutella xylostella Granulosis virus, I + Cydia pomonella Granulosis virus, I + Harpin, I + Imicyafos, I + Heliothis virescens Nucleopolyhedrovirus, I + Heliothis punctigera

Nucleopolyhedrovirus, I + Helicoverpa armigera Nucleopolyhedrovirus, I + Helicoverpa zea

Nucleopolyhedrovirus, I + Spodoptera frugiperda Nucleopolyhedrovirus, I + Plutella xylostella

Nucleopolyhedrovirus, I + Pasteuria nishizawae , I + p-cymene, I + Pyflubumide, I + Pyrafluprole, I + pyrethrum, I + QRD 420, I + QRD 452, I + QRD 460, I + Terpenoid blends, I + Terpenoids, I +

Tetraniliprole, and I + oterpinene;

Composition also include mixtures of compound of formula I and an active substance referenced by a code, such as I + code AE 1887196 (BSC-BX60309), I + code NNI-0745 GR, I + code IKI-3106, I + code JT-L001 , I + code ZNQ-08056, I + code IPPA152201 , I + code HNPC-A9908 (CAS: [66041 1-21-2]), I + code HNPC-A2005 (CAS: [860028-12-2]), I + code JS1 18, I + code ZJ0967, I + code ZJ2242, I + code JS71 19 (CAS: [929545-74-4]), I + code SN-1 172, I + code HNPC-A9835, I + code HNPC-A9955, I + code HNPC-A3061 , I + code Chuanhua 89-1 , I + code IPP-10, I + code ZJ3265, I + code JS91 17, I + code SYP-9080, I + code ZJ3757, I + code ZJ4042, I + code ZJ4014, I + code ITM-121 , I + code DPX-RAB55 (DKI-2301 ), I + code Me5382, I + code NC-515, I + code NA-89, I + code MIE-1209, I + code MCI-8007, I + code BCS-CL73507, I + code S-1871 , I + code DPX-RDS63, and I + code AKD-1 193.

The compounds of formula I according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which have a favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants. Compounds of formula I may act against all or only individual developmental stages of normally sensitive, but also resistant, animal pests, such as insects or representatives of the order Acarina. The insecticidal or acaricidal activity of the compounds can manifest itself directly, i. e. in destruction of the pests, which takes place either immediately or only after some time has elapsed, for example during ecdysis, or indirectly, for example in a reduced oviposition and/or hatching rate, a good activity corresponding to a destruction rate (mortality) of at least 50 to 60%.

Examples of the abovementioned animal pests are:

from the order Acarina, for example, Acalitus spp, Aculus spp, Acaricalus spp, Aceria spp, Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp, Eotetranychus spp, Eriophyes spp., Hemitarsonemus spp, Hyalomma spp., Ixodes spp., Olygonychus spp, Ornithodoros spp.,

Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp, Polypha- gotarsonemus spp, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp.,

Steneotarsonemus spp, Tarsonemus spp. and Tetranychus spp. ;

from the order Anoplura, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp. ;

from the order Coleoptera, for example, Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis, Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp, Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa decemLineata, Lissorhoptrus spp., Liogenys spp, Maecolaspis spp, Maladera castanea, Megascelis spp, Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp, Phlyctinus spp., Popillia spp., Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Somaticus spp, Sphenophorus spp, Sternechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp. ; from the order Diptera, for example, Aedes spp., Anopheles spp, Antherigona soccata,Bactrocea oleae, Bibio hortulanus, Bradysia spp, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp, Drosophila melanogaster, Fannia spp., Gastrophilus spp., Geomyza tripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis spp, Rivelia quadrifasciata, Scatella spp, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.;

from the order Hemiptera, for example, Acanthocoris scabrator, Acrosternum spp, Adelphocoris lineolatus, Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp., Clavigralla tomentosicollis, Creontiades spp, Distantiella theobroma, Dichelops furcatus, Dysdercus spp., Edessa spp, Euchistus spp., Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp, Margarodes spp, Murgantia histrionic, Neomegalotomus spp, Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis, Piesma spp., Piezodorus spp, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp. , Thyanta spp , Triatoma spp. , and Vatiga illudens; from the order homoptera, for example, Acyrthosium pisum, Adalges spp, Agalliana ensigera,

Agonoscena targionii, Aleurodicus spp, Aleurocanthus spp, Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp., Aonidiella auranti, Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp, Brachycaudus spp, Brevicoryne brassicae, Cacopsylla spp, Cavariella aegopodii Scop., Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp, Cofana spectra, Cryptomyzus spp, Cicadulina spp, Coccus hesperidum, Dalbulus maidis, Dialeurodes spp, Diaphorina citri, Diuraphis noxia, Dysaphis spp, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp, Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp., Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxera spp, Planococ- cus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina, Toxoptera spp, Trialeurodes spp, Tridiscus sporoboli, Trionymus spp, Trioza erytreae , Unaspis citri, Zygina flammigera, and Zyginidia scutellaris;

from the order Hymenoptera, for example, Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp. and Vespa spp.;

from the order Isoptera, for example, Coptotermes spp, Corniternes cumulans, Incisitermes spp, Macrotermes spp, Mastotermes spp, Microtermes spp, Reticulitermes spp.; Solenopsis geminate;

from the order Lepidoptera, for example, Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp,

Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp, Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp., Eldana saccharina, Ephestia spp., Epinotia spp, Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp, Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella,

Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp, Noctua spp, Operophtera spp., Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Papaipema nebris, Pectinophora gossypiela, Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Pseudoplusia spp, Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp.,

Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta, and Yponomeuta spp.;

from the order Mallophaga, for example, Damalinea spp. and Trichodectes spp.;

from the order Orthoptera, for example, Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp. , Scapteriscus spp, and Schistocerca spp.;

from the order Psocoptera, for example, Liposcelis spp.;

from the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp. and

Xenopsylla cheopis;

from the order Thysanoptera, for example, Calliothrips phaseoli, Frankliniella spp., Heliothrips spp, Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp; and/or

from the order Thysanura, for example, Lepisma saccharina.

Examples of soil-inhabiting pests, which can damage a crop in the early stages of plant development, are:

from the order Lepidoptera, for example, Acleris spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Autographa spp., Busseola fusca, Cadra cautella, Chilo spp., Crocidolomia binotalis, Diatraea spp., Diparopsis castanea, Elasmopalpus spp., Heliothis spp., Mamestra brassicae, Phthorimaea operculella, Plutella xylostella, Scirpophaga spp., Sesamia spp., Spodoptera spp. and Tortrix spp.;

from the order Coleoptera, for example, Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnema tibialis, Conotrachelus spp., Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Dilopoderus spp., Epilachna spp., Eremnus spp., Heteronychus spp., Lissorhoptrus spp.,

Melolontha spp., Orycaephilus spp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitotroga spp., Somaticus spp., Tanymecus spp., Tenebrio spp., Tribolium spp., Trogoderma spp. and Zabrus spp.;

from the order Orthoptera, for example, Gryllotalpa spp.;

from the order Isoptera, for example, Reticulitermes spp.;

from the order Psocoptera, for example, Liposcelis spp.; from the order Anoplura, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.;

from the order Homoptera, for example, Eriosoma larigerum;

from the order Hymenoptera, for example, Acromyrmex, Atta spp., Cephus spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.;

from the order Diptera, for example, Tipula spp.;

crucifer flea beetles (Phyllotreta spp.), root maggots (Delia spp.), cabbage seedpod weevil (Ceutorhynchus spp.) and aphids.

The compounds of formula (I) may be useful for the control of nematodes. Thus, in a further aspect, the invention also relates to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita,

Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Eelonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes,

Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Pratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species, such as Subanguina., spp Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp..

In particular, the nematode species Meloidogyne spp., Heterodera spp., Rotylenchus spp. and Pratylenchus spp. can be controlled by the present inventive compounds.

Crops of useful plants in which the composition according to the invention can be used include perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.

Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).

Crops are to be understood as also including those crops which have been rendered tolerant to herbicides like bromoxynil or classes of herbicides such as ALS-, EPSPS-, GS-, HPPD- and PPO- inhibitors. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer canola. Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate- resistant maize varieties commercially available under the trade names Round upReady®, Herculex I® and LibertyLink®.

Crops are also to be understood as being those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include δ- endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.

An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds). An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification). For example, a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

The compounds according to the invention can be used as pesticidal agents in unmodified form, but they are generally formulated into compositions in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances. The formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on

Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can either be used directly or diluted prior to use. The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.

The formulations can be prepared e.g. by mixing the active ingredient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.

The active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art.

Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.

The formulation adjuvants that are suitable for the preparation of the compositions according to the invention are known per se. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane,

cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, A/,A/-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1 ,1 , 1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone,

isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, A/-methyl-2-pyrrolidone and the like. _7g

Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.

A large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use. Surface- active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonat.es, such as sodium

dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2- ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as

lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di- alkylphosphate esters; and also further substances described e.g. in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981 ).

Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.

The compositions according to the invention can include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of C₈-C₂2 fatty acids, especially the methyl derivatives of Ci₂-Ci₈ fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10^th Edition, Southern Illinois University, 2010.

The inventive compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to

95 % by weight, of compounds of the present invention and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance. Whereas commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.

The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.

Preferred formulations can have the following compositions (weight %):

Emulsifiable concentrates:

active ingredient: 1 to 95 %, preferably 60 to 90 %

surface-active agent: 1 to 30 %, preferably 5 to 20 %

liquid carrier: 1 to 80 %, preferably 1 to 35 %

Dusts:

active ingredient: 0.1 to 10 %, preferably 0.1 to 5 %

solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %

Suspension concentrates:

active ingredient: 5 to 75 %, preferably 10 to 50 %

water: 94 to 24 %, preferably 88 to 30 %

surface-active agent: 1 to 40 %, preferably 2 to 30 %

Wettable powders:

active ingredient: 0.5 to 90 %, preferably 1 to 80 %

surface-active agent: 0.5 to 20 %, preferably 1 to 15 %

solid carrier: 5 to 95 %, preferably 15 to 90 %

Granules:

active ingredient: 0.1 to 30 %, preferably 0.1 to 15 %

solid carrier: 99.5 to 70 %, preferably 97 to 85 %

The following Examples further illustrate, but do not limit, the invention.

The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

Powders for drv seed treatment a) b) c)

active ingredients 25 % 50 % 75 %

light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % -

Kaolin 65 % 40 % -

Talcum - 20

The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

Ready-for-use dusts are obtained by mixing the combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

The combination is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner. Suspension concentrate

The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

Flowable concentrate for seed treatment

Slow Release Capsule Suspension

28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8: 1 ). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

The Examples which follow serve to illustrate the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, _

-83- using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.8 ppm.

The following abbreviations were used in this section: DMF: dimethylformamide; THF:

tetrahydrofuran; EtOAc : ethyl acetate; s = singlet; bs = broad singlet; d = doublet; dd = double doublet; dt = double triplet; t = triplet, tt = triple triplet, q = quartet, sept = septet; m = multiplet; Me = methyl; Et = ethyl; Pr = propyl; Bu = butyl; M.p. = melting point; RT = retention time, [M+H]⁺ = molecular mass of the molecular cation, [M-H]^" = molecular mass of the molecular anion.

Preparation Examples

Reaction conditions:

(a) ethyl 2-sulfinylacetate, Ν,Ν,Ν-Triethylamine, THF (b) LiOH, THF, H₂0 (c) Mesyl chloride, Pyridine (d) DMF (e) BBr₃, DCM (f) K₂C0₃, Acetone (g) LiOH, THF, H₂0 (h) bis(dimethylamino)methylene- (triazolo[4,5-b]pyridin-3-yl)oxonium hexafluorophosphate Ν,Ν,Ν-Triethylamine, DMF.

Preparation of Ethyl 3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-3-hydroxy-5- (trifluoromethyl)tetrahydrothiophene-2-carboxylate

To a solution of (Z)-1-(3-bromo-4-tert-butylsulfanyl-phenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-en- 1-one (10 g) in tetrahydrofuran (100 mL). Ethyl 2-sulfanylacetate (6.96 g) and triethylamine (9.6 g) was added. The reaction was stirred at room temperature under nitrogen atmosphere for overnight. After completion of reaction, monitored by TLC, the reaction mass was evaporated off under reduced pressure, diluted with water (150 mL) and extracted with ethyl acetate (2 x 100mL). The combined organic layer was dried over sodium sulphate, evaporated off under reduced pressure. Thus obtained compound was purified by column chromatography.

LCMS (Method A) RT 2.73 min [M+23] 654.

H NMR (CDCI₃, 400 MHz,) δ: 7.82 (d, 1 H), 7.66 (dd, 1 H), 7.50-7.52(m, 2H), 7.36-7.38 (m, 2H), 4.71 (s, 1 H), 4.57 (s, 1 H), 4.14 (q, 2H), 2.99 (d, 1 H), 2.87 (d, 1 H) 1.36 (s, 9H), 1.17 (t, 3H).

Preparation of 3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-3-hydroxy-5- (trifluoromethyl)tetrahydrothiophene-2-carboxylic acid

To a solution of ethyl 3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-3-hydroxy-5- (trifluoromethyl)tetrahydrothiophene-2-carboxylate (8g) in tetrahydrofuran(100ml) was added lithium hydroxide (576 mg) in water (5mL). The reaction was stirred at room temperature for overnight. After completion of reaction monitored by TLC, reaction mass was concentrated under reduced pressure, diluted with water (15mL), acidified with 5% HCI solution (10 mL) and extracted with ethyl acetate (2 x l OOmL). The combined organic layer was washed with water (50mL), dried over sodium sulphate, evaporated off under reduced pressure. Thus obtained compound was preceded for next step without any characterization.

Preparation of 4-(3-bromo-4-tert-butylsulfanyl-phenyl)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)- 3H-thiophene

To a solution of (5S)-3-(3-bromo-4-tert-butylsulfanyl-phenyl)-5-(3,5-dichlorophenyl)-3-hydroxy-5- (trifluoromethyl)tetrahydrothiophene-2-carboxylic acid (7.5 g) in pyridine (30 mL) and followed addition of methanesulfonyl chloride (3.03 g) at 0 °C and stirring was continued at room temperature for overnight. After completion of reaction (monitored by thin layer chromatography), the reaction mass was diluted with water (15ml_), extracted with ethyl acetate (3 x 60ml_). The combined organic layer was dried over sodium sulphate and evaporated off under reduced pressure.

Thus obtained 5-(3-bromo-4-tert-butylsulfanyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-6-oxa-2- thiabicyclo[3.2.0]heptan-7-one ( 6 g, 12.4 mmol) was diluted with in N,N-dimethylformamide (30 mL) heating was applied at 100 °C for 2hr. After completion of reaction monitored by TLC, the reaction mass was diluted with water (100ml_) extracted with ethyl acetate (3 x 40ml_). The combined organic layer was washed with water (2 x 50ml_), dried over sodium sulphate and evaporated off under reduced pressure.

Thus obtained crude mixture was purified by column chromatography to get desired product.

LCMS (Method A) RT 2.64 min [M+H]⁺ 540.8.

H NMR (CDCI₃, 400 MHz,) δ: 7.59-7.63 (m, 2H), 7.38-7.41 (m, 2H), 7.25-7.26 (m, 2H), 6.61 (s, 1 H), 3.83

(d, 1 H), 3.60 (d, 1 H).

Preparation of 2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]benzenethiol

4-(3-bromo-4-tert-butylsulfanyl-phenyl)-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophene (1 g) in methylene chloride (15 mL) boron tribromide (1.38 g) was added at 0 °C and stirring was continued at 0 °C for 2hr. After completion of the reaction mass was quenched with methanol (0.3 ml) and diluted with ice cold water (10mL) and extracted with DCM (2 x 20mL). The combined organic layer was washed with „„

-86- water (30ml_), dried over sodium sulphate and evaporated off under reduced pressure. Thus obtained crude mixture was purified by column chromatography to get desired product.

LCMS (Method A) RT 2.73 min [Μ-ΗΓ 484.8 (-ESI)

H NMR (CDCI₃, 400 MHz,) δ: 7.37-7.49(m, 5H), 7.08(dd, 1 H), 6.40 (s, 1 H), 3.70 (d, 1 H), 3.51 (d, 1 H).

Preparation of ethyl 2-[2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4- yl]phenyl]sulfinylacetate

To a solution of 2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]benzenethiol (0.87 g) in acetone (15 mL), potassium carbonate (0.5g) and ethyl 2-bromoacetate(0.32g ) was added and the reaction mixture was stirred at 40 °C under nitrogen for overnight (4 h). The completion of the reaction was monitored by Thin Layer Chromatography (TLC). After the completion of the reaction solvent was evaporated under reduced pressure and the reaction mixture was diluted with ethyl acetate (50 ml), washed with water (45 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 15 % ethyl acetate and cyclohexane as an eluent.

H NMR (CDCI₃, 400 MHz,) δ: 7.98 (d, 1 H), 7.61 (d, 1 H), 7.26-7.41 (d, 4H), 6.63(s, 1 H), 4.21-4.26 (t, 2H), 3.82 (s, 2H), 1.28-1.31 (t, 3H),

Preparation of 2-[2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4- yl]phenyl]sulfanylacetic acid

To a stirring solution ethyl 2-[2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4- yl]phenyl]sulfanylacetate (1g) in tetrahydrofuran (20 mL), lithium hydroxide solution (0.1g in 4 mL water) was added and the stirring was continued for two hours at room temperature. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was acidified with a solution of hydrochloric acid (2N), extracted with ethyl acetate (35 ml), washed with water (30 mL x 2), dried over sodium sulphate and the solvent was evaporated under reduced pressure.

To a stirring solution of solution of 2-[2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen- 4-yl]phenyl]sulfanylacetic acid(0.2g) in DMF bis(dimethylamino)methylene-(triazolo[4,5-b]pyridin-3- yl)oxonium hexafluorophosphate(0.2g), N,N,N-Triethylamine(0.1g) and ethyl amine (0.03g) was added. The mixture was stirred at room temperature for hour. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (35 ml), washed with water (30 mL x 2), dried over sodium sulphate and the solvent was evaporated under reduced pressure.

LCMS (Method B) RT 6.45 min [M+H]⁺ 569.95.

H NMR (CDCI₃, 400 MHz,) δ: 7.61 (d, 1 H), 7.44-7.45 (m, 3H), 7.1 1-7.19 (m, 1 H), 7.04-7.06 (d, 1 H), 6.62- 6.64(m, 1 H),6.47(s, 1 H), 3.70-3.75 (dd, 1 H), 3.50-3.61 (m, 3H), 3.17-3.24 (q, 2H), 1.00-1.03 (m, 3H). Preparation of 2-[2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4- yl]phenyl]sulfanyl-N-(2,2,2-trifluoroeth l)acetamide [A-2]

LCMS (Method A) RT 2.60 min [M+H]⁺ 626

H NMR (CDCI₃, 400 MHz,) δ: 7.54 (d, 1 H), 7.38-7.40 (m, 3H), 7.26 (m, 1 H), 7.13 (d, 1 H), 6.55(d, 1 H), 6.45(s, 1 H), 3.87-3.89 (m, 2H), 3.72-3.77 (m, 4H). Preparation of 2-[2-bromo-4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4- yl] pheny l]su Ifanyl -N -cyclopropyl -acetam ide [A-3]

LCMS (Method B) RT 6.4 min [M+H]⁺ 581.85.

H NMR (CDCI₃, 400 MHz,) δ: 7.51 (d, 1 H), 7.38-7.40 (m, 3H), 7.27 (d, 1 H), 7.13 (d, 1 H), 6.75(d,

1 H),6.54(s, 1 H), 3.77-3.81 (dd, 1 H), 3.57-3.65 (m, 3H), 2.67-2.68 (m, 1 H), 0.70-0.76 (m, 2H), 0.41-0.43 (m, 2H).

Table A. Compounds of formal I-

Synthetic Scheme B-1

Reaction conditions

(a) Ethylchloroformate, N,N,N-Triethylamine,NaBH4, THF, H₂0 (b) ) Mesylchloride, Ν,Ν,Ν-Triethylamine, THF, (c) NaN3, DMF (d) Triphenylphosphan,THF, H₂0 (e) Acid chloride, Ν,Ν,Ν-Triethylamine, DCM.(f) methylsulfanylsodium, DMF

Preparation of [4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl- phenyl]methanol

To a solution of 4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl-benzoic acid (200mg) in tetrahydrofuran (3ml), Ν,Ν,Ν-Triethylamine (0.063mL) was added. The reaction was cooled to 0 °C Ethylchloroformate (0.05ml_) was added under nitrogen atmosphere and stirring was continued for three hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered and washed with THF (10 ml). Thus obtained filtrate was taken in round bottom flask Sodium borohydride (45mg dissolved in water 2ml_) was added at 0 °C and stirring was continued for 2h. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ethylacetate (30 ml), washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 25 % ethyl acetate and cyclohexane as an eluent.

LCMS (Method A) RT 2.47 min [M+H]⁺ .

H NMR (CDCI₃, 400 MHz,) δ: 7.31-7.44 (m, 4H), 7.12-7.16 (m, 2H), 6.41 (s, 1 H), 4.62 (s, 2H), 3.76(d, 1 H), 3.50(d, 1 H), 2.29 (s, 3H).

Preparation of [4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl- phen l]methyl methanesulfonate

To a solution of [4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl-phenyl]methanol in tetrahydrofuran (5 mL), N,N,N-Triethylamine(1.1g) was added. The reaction was cooled to 0 °C acetyl chloride (0.41g) was added under nitrogen atmosphere and stirring was continued for three hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with dichloromethane (30 ml), washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure

H NMR (CDCI₃, 400 MHz,) δ: 7.31-7.36 (m, 3H), 7.09-7.24 (m, 3H), 6.41 (s, 1 H), 4.47 (s, 2H), 3.76 (d, 1 H), 3.58 (d, 1 H), 2.92 (s, 3H), 2.27 (s, 3H).

Preparation of 2-(3,5-dichlorophenyl)-4-[4-[[(imino-$l^A{5}-azanylidene)amino]methyl]-3-methyl- phenyl]-2-(trifluoromethyl)-3H-thiophene

To a solution of [4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl-phenyl]methyl methanesulfonate (0.7 g) in Dimethylformamide (20 mL), Sodium azide (0.27g) was added. The reaction mixture was stirred at 80 °C for over hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 ml), washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 20 % ethyl acetate and cyclohexane as an eluent.

H NMR (CDCI₃, 400 MHz,) δ: 7.37-7.43 (m, 3H), 7.20-7.26 (m, 3H), 6.52 (s, 1 H), 4.32 (s, 2H), 3.84(d, 1 H), 3.62(d, 1 H), 2.37 (s, 3H).

Preparation of [4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl-phenyl] methanamine

To a solution of 4-[4-(azidomethyl)-3-methyl-phenyl]-2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H- thiophene (0.2 g) in tetrahydrofuran (5 mL) triphenylphosphane (0.14 g) was added followed by addition of water (1 mL). The reaction mixture was stirred at room temperature for two overnight. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 ml), washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 90 % ethyl acetate and cyclohexane as an eluent.

LCMS (Method B) RT 4.44 min [M+H]⁺ 415.96

Preparation of N-[[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl- phenyl]methyl]cyclopropanecarboxamide [B-1]

To a solution of [4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl- phenyl]methanamine (0.2 g) in dichloromethane (5 mL), N,N,N-Triethylamine(0.087g) was added. The reaction was cooled to 0 °C cyclopropanecarbonyl chloride (0.045g) was added under nitrogen atmosphere and stirring was continued for three hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with dichloromethane (30 ml), _

-92- washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 25 % ethyl acetate and cyclohexane as an eluent.

LCMS (Method A) RT 2.44 min [M+H]⁺ 486.0.

H NMR (CDCI₃, 400 MHz,) δ: 7.43 (d, 2H), 7.36-7.38 (m, 1 H), 7.16-7.21 (m, 3H), 6.48 (s, 1 H), 5.69 (s, 1 H), 4.44(d, 2H), 3.84(d, 1 H), 3.67(d, 1 H), 2.34 (s, 3H), 1.34-1.38 (m, 1 H), 1.01-1.04(m, 2H), 0.73-0.75 (m, 2H).

N-[[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl-phenyl]methyl]-2- methyl-propanamide [B-2]

LCMS (Method A) RT 2.47 min [M+H]⁺ 487.9.

H NMR (CDCI₃, 400 MHz,) δ: 7.30-7.36 (m, 3H), 7.09-7.1 1 (m, 3H), 6.41 (s, 1 H), 5.54 (s, 1 H), 4.35(d, 2H), 3.79(d, 1 H), 3.58(d, 1 H), 2.29 (s, 3H), 2.32-2.32 (m, 1 H), 1.10 (d, 6H).

2-chloro-N-[[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl- phenyl]methyl]acetamide [B-4]

LCMS (Method A) RT 2.45 min [M+H]⁺ 495.8

H NMR (CDCI₃, 400 MHz,) δ: 7.31-7.36 (m, 3H), 7.1 1-7.16 (m, 3H), 6.72 (s, 1 H), 6.43(s, 1 H), 4.41 (d, 2H), 4.04(s, 2H), 3.78(d, 1 H), 3.57(d, 1 H), 2.28 (s, 3H).

N-[[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl- phenyl]methyl]propanamide [B-3]

LCMS (Method A) RT 2.43 min [M+H]⁺ 473.9.

H NMR (CDCI₃, 400 MHz,) δ: 7.31-7.36 (m, 3H), 7.09-7.14 (m, 3H), 6.41 (s, 1 H), 5.42(s, 1 H), 4.36(d, 2H), 3.76(d, 1 H), 3.56(d, 1 H), 2.27 (s, 3H), 2.16.(q, 2H), 1.1 1 (t, 3H).

2-bromo-N-[[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl- phenyl]methyl]acetamide

LCMS (Method B) RT 5.39 min [M+H]⁺ 537.66.

Preparation of N-[[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl- phenyl]methyl]-2-methylsulfanyl-acetamide [B-5]

To a solution of 2-bromo-N-[[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]-2-methyl- phenyl]methyl]acetamide (0.1 g) in Dimethylformamide (20 mL) methylsulfanylsodium( 0,039g) was added. The reaction mixture was stirred at 80 °C for two hours. The completion of the reaction was „

-94- monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 ml), washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 10 % ethyl acetate and cyclohexane as an eluent. LCMS (Method B) RT 5.41 min [M+H]⁺ 505.79.

H NMR (CDCI₃, 400 MHz,) δ: 7.31-7.36 (m, 3H), 7.10 -7.16 (m, 3H), 6.93 (s, 1 H), 6.42(s, 1 H), 4.41 (d, 2H), 3.78(s, 2H), 3.58(d, 1 H), 3.18(s, 2H), 2.28 (s, 3H) 2.05 (s, 3H).

Table B. Compounds of formal I-

Synthetic Scheme C-1

Reaction conditions

(a) (BOC)₂0, Toluene (b) tributyl(1-ethoxyvinyl)stannane, 3-diphenylphosphanylpropyl(diphenyl) phosphane, palladium(ll)acetate, DMF (c) 1-(3,5-dichlorophenyl)-2,2,2-trifluoro-ethanone, K₂C0₃, CH₃CN 5 (d) ethyl 2-sulfinylacetate, Ν,Ν,Ν-Triethylamine, THF (e) LiOH, THF, H₂0 (f) Mesylchloride, Pyridine (g) DMF (h) HCI (IN) in dioxane (i) Acid chloride, Ν,Ν,Ν-Triethylamine, THF

Preparation of tert-butyl N-[(1S)-1 - 4-bromophenyl)ethyl]-N-tert-butoxycarbonyl-carbamate

10 (1 S)-1-(4-bromophenyl)ethanamine (3g) in two neck round bottom flask tert-butoxycarbonyl tert-butyl carbonate (14 g) was added drop wise over period of 10 min and stirring was applied vigorously. After two min the solid was precipitated out from the reaction mass and exothermic was observed. Thus obtained solid (tert-butyl N-[(1 S)-1-(4-bromophenyl) ethyl]carbamate) was taken in toluene tert-butoxycarbonyl tert-butyl carbonate (40g) was added. The reaction was stirred at 1 10 °C under nitrogen atmosphere for

15 48h. The completion of reaction was monitored by Thin Layer Chromatography (TLC). After the _

-96- completion of reaction solvent was evaporated under reduced pressure and crude residue was purified by column chromatography using 10% ethyl acetate and cyclohexane as an eluent.

LCMS (Method A) RT 2.3 min [M+23] 398.1.

H NMR (CDCI₃, 400 MHz,) δ: 7.46 (d, 2H), 7.26 (d, 2H), 5.48-5.50 (m, 1 H), 1.57-1.59 (d, 3H), 1.43 (s, 18H).

Preparation of tert -butyl N-[(1S)-1 -(4-acetylphenyl)ethyl]-N-tert-butoxycarbonyl-carbamate

To a solution of tert-butyl N-[(1 S)-1-(4-bromophenyl)ethyl]-N-tert-butoxycarbonyl-carbamate (12 g) in N,N-dimethylformamide (100 mL) tributyl(1-ethoxyvinyl)stannane ( 16.25g), 3-diphenylphosphanyl propyl(diphenyl)phosphane (1.05g) and palladium(ll) acetate (0.21g) was added . The reaction mass was stirred at 120 °C under nitrogen atmosphere for 12h. The completion of reaction was monitored by Thin Layer Chromatography (TLC). After completion of the reaction reaction mixture was diluted with ethyl acetate (200 ml), washed with hydrochloric acid (2N in water) (200 mL x 2) followed by with water (200 mL) and dried over sodium sulphate. The combined organic phases were evaporated under reduced pressure and the crude residue was purified by column chromatography using 10 % ethyl acetate and cyclohexane as an eluent.

H NMR (CDCI₃, 400 MHz,) δ: 7.86 (d, 2H), 7.40 (d, 2H), 5.45-5.46 (m, 1 H), 2.56 (s, 3H), 1.46 (s, 3H), 1.32(s, 18H)

To a solution of tert-butyl N-[(1 S)-1-(4-acetylphenyl)ethyl]-N-tert-butoxycarbonyl-carbamate (1 Og) in acetonitrile (50 imL), 1-(3,5-dichlorophenyl)-2,2,2-trifluoro-ethanone(8g) and potassium carbonate (0.76g) was added and the reaction mixture was stirred at 90 °C under nitrogen for overnight (25 h). The completion of the reaction was monitored by Thin Layer Chromatography (TLC). After the completion of the reaction solvent was evaporated under reduced pressure and the reaction mixture was diluted with ethyl acetate (50 ml), washed with water (45 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 15 % ethyl acetate and cyclohexane as an eluent.

LCMS (Method B) RT 5.5 min [M-H]^" 587.06

H NMR (CDCI₃, 400 MHz,) δ: 7.75 (d, 2H), 7.09-7.38 (m, 7H), 5.44-5.46 (m, 1 H), 1.32-1.36 (m, 21 H),

Preparation of ethyl 3-[4-[(1S)-1 -[tert-butoxycarbonyl(isopropoxycarbonyl)amino]ethyl]phenyl]-5- (3,5-dichlorophenyl)-3-hydroxy-5-(trifluoromethyl)tetrahydrothiophene-2-carboxylate

To a stirring solution of tert-butyl N-tert-butoxycarbonyl-N-[(1 S)-1-[4-[(Z)-3-(3,5-dichlorophenyl)-4,4,4- trifluoro-but-2-enoyl]phenyl]ethyl]carbamate_(14.4 g) ) in tetrahydrofuran(140ml_) ethyl 2-sulfinylacetate (8.82g) was added followed by the addition of Ν,Ν,Ν-Triethylamine (1.25g). The reaction mass was stirred at room temperature overnight. The completion of the reaction was monitored by Thin Layer Chromatography (TLC). After completion of the reaction, the reaction mixture was evaporated under reduced pressure, was diluted with ethyl acetate (150 ml), washed with water (125 ml x 2) and dried over sodium sulphate. The combined organic phases were evaporated under reduced pressure and the crude residue was purified by column chromatography using 10 % ethyl acetate and cyclohexane as an eluent.

Preparation of 3-[4-[(1S)-1 -[tert-butoxycarbonyl(isopropoxycarbonyl)amino]ethyl]phenyl]-5-(3,5- dichlorophenyl)-3-hydroxy-5-(trifluoromethyl)tetrahydrothiophene-2-carboxylic acid

To a stirring solution ethyl 3-[4-[(1 S)-1-[tert-butoxycarbonyl(isopropoxycarbonyl)amino]ethyl]phenyl]-5- (3,5-dichlorophenyl)-3-hydroxy-5-(trifluoromethyl)tetrahydrothiophene-2-carboxylate(1.6g) in

tetrahydrofuran (30 mL), lithium hydroxide solution (0.12g in 8 mL water) was added and the stirring was continued for two hours at room temperature. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was acidified with a solution of hydrochloric acid (2N), extracted with ethyl acetate (35 ml), washed with water (30 mL x 2), dried over sodium sulphate and the solvent was evaporated under reduced pressure. Preparation of isopropyl N-tert-butoxycarbonyl-N-[(1S)-1 -[4-[3-(3,5-dichlorophenyl)-7-oxo-3- (trifluoromethyl)-6-oxa-2-thiabicyclo[3.2.0]heptan-5-yl]phenyl]ethyl]carbamate

To a solution of 3-[4-[(1 S)-1-[tert-butoxycarbonyl(isopropoxycarbonyl)amino]ethyl]phenyl]-5-(3,5- dichlorophenyl)-3-hydroxy-5-(trifluoromethyl)tetrahydrothiophene-2-carboxylic acid (1.25g ) in pyridine (8 mL) cooled to 0 °C methanesulfonyl chloride (0.65g) was added. The reaction was stirred at room temperature overnight. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was acidified with a solution of hydrochloric acid (2N), extracted with ethyl acetate (35 ml), washed with water (30 mL x 2), dried over sodium sulphate and the solvent was evaporated under reduced pressure. The combined organic phases were evaporated under reduced pressure and the crude residue was purified by column chromatography using 10 % ethyl acetate and cyclohexane as an eluent. Preparation of isopropyl N-tert-butoxycarbonyl-N-[(1S)-1-[4-[2-(3,5-i dichlorophenyl)-2- (trifluoromethyl)-3H-thiophen-4-yl]phenyl]ethyl]carbamate

To a solution of isopropyl N-tert-butoxycarbonyl-N-[(1 S)-1-[4-[3-(3,5-dichlorophenyl)-7-oxo-3- (trifluoromethyl)-6-oxa-2-thiabicyclo[3.2.0]heptan-5-yl]phenyl]ethyl]carbamate (1.13 g) in

Dimethylformamide (15 mL), the reaction mixture was stirred at 120 °C for two hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 ml), washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 10 % ethyl acetate and cyclohexane as an eluent.

LCMS (Method A) RT 1.8 min [M+H]⁺ 615.5

H NMR (CDCI₃, 400 MHz,) δ: 7.42 (s, 2H), 7.36-7.38 (m, 1 H), 7.26-7.35 (m, 4H), 6.46 (s, 1 H), 5.48 (q, 1 H), 3.80-3.88 (m, 1 H), 3.63 (d, 1 H), 1.65-1.74 (m, 3H), 1.36-1.45 (m, 18H),

Preparation of (1S)-1-[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4- yl]phenyl]ethanamine

To a solution of of isopropyl N-tert-butoxycarbonyl-N-[(1 S)-1-[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)- 3H-thiophen-4-yl]phenyl]ethyl]carbamate (1.2 g) in dichloromethane (5 mL), HCI in dioxane solution (20% solution) was added. The reaction was stirred at 0 °C five hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with toluene and evaporated under reduced pressure. Preparation of N-[(1S)-1 -[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4- yl]phenyl]ethyl]cyclopropanecarboxamide [C-1]

To a solution of (1 S)-1-[4-[2-(3,5-dichlorophenyl)-2-(trifluorometh^

Hydrochloride (0.15 g) in dichloromethane (2 mL), N,N,N-Triethylamine( 0.073g) was added. The reaction was cooled to 0 °C cyclopropyl chloride (0.038g) was added under nitrogen atmosphere and stirring was continued for three hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with dichloromethane (30 ml), washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 25 % ethyl acetate and cyclohexane as an eluent.

LCMS (Method B) RT 5.3 min [M+H]⁺ 485.89

H NMR (CDCI₃, 400 MHz,) δ: 7.19-7.35 (m, 7H), 6.39 (s, 1 H), 5.84 (d, 1 H), 5.04 (d, 1 H), 3.77 (dd, 1 H), 3.56 (dd, 1 H), 1.85-1.95 (m, 1 H),1.41-144 (d, 3H), 0.87-0.90 (m, 2H), 0.62-0.68 (m, 2H). Preparation of N-[(1S)-1 -[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4- yl]phenyl]ethyl]-3,3,3-trifluoro-propanamide [C-3]

LCMS (Method B) RT 5.3 min [M+H]⁺ 527.78

H NMR (CDCI₃, 400 MHz,) δ: 7.34-7.37 (m, 2H), 7.29-7.32 (m, 1 H), 7.23-7.27 (m, 2H), 7.17-7.22 (m, 2H), 6.42 (s, 1 H), 6.01 (d, 1 H), 4.98-5.08 (m, 1 H), 3.77 (dd, 1 H), 3.76 (dd, 1 H), 2.93-3.03 (m, 2H), 1.43 (d, 3H)

Preparation of N-[(1S)-1 -[4-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4- yl]phenyl]ethyl]propanamide [C-2]

LCMS (Method B) RT 5.3 min [M+H]⁺ 473.92

H NMR (CDCI₃, 400 MHz,) δ: 7.34-7.38 (m, 2H), 7.29-7.32 (m, 1H), 7.18-7.28 (m, 4H), 6.40 (s, 1H), 5.58 (d, 1H), 5.02-5.08 (m, 1H), 3.77 (dd, 1H), 3.56 (dd, 1H), 2.09-2.19 (m, 2H), 1.41 (d, 3H), 1.04-1.11 (m, 3H)

Table C. Compounds of formal I-

Reaction conditions (a) (BOC)₂0, Toluene (b) 1-(3,5-dichlorophenyl)-2,2,2-trifluoro-ethanone K₂C0₃,CH₃CN (c) ethyl 2- sulfinylacetate, Ν,Ν,Ν-Triethylamine, THF (d) LiOH, THF, H₂0 (e) Mesylchloride, Pyridine (f) DMF (g) HCI IN dioxane (h) Acid chloride, Ν,Ν,Ν-Triethylamine, THF. Preparation of tert -butyl N-(5-acetylindan-1 -yl)-N-tert-butoxycarbonyl-carbamate

To a solution of tert-butyl N-(5-acetylindan-1-yl)carbamat (3 g) in toluene (35 mL), tert-butoxycarbonyl tert-butyl carbonate (23.77g) was added followed by addition of DMAP (4mg) was added. The reaction mixture was stirred at 90 °C under nitrogen atmosphere for 20h. The completion of reaction was monitored by Thin Layer Chromatography (TLC). After the completion of reaction solvent was evaporated under reduced pressure and crude residue was purified by column chromatography using 10% ethyl acetate and cyclohexane as an eluent.

H NMR (CDCI₃, 400 MHz,) δ: 7.78 (d, 1 H), 7.23-7.26 (m, 2H), 5.82-5.85 (m, 1 H), 3.10-3.1 1 (m, 1 H), 2.93-3.08 (m, 1 H), 2.59 (s, 3H), 2.50-2.52 (m, 1 H), 2.33-2.37 (m, 1 H )1 .55 (s, 9H), 1.41 (s, 9H).

Preparation of tert-butyl N-tert-butoxycarbonyl-N-[5-[(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but- 2-enoyl]indan-1 -yl]carbamate

To a solution of tert-butyl N-(5-acetylindan-1-yl)-N-tert-butoxycarbonyl-carbamate(3g) in acetonitrile (50 mL), 1-(3,5-dichlorophenyl)-2,2,2-trifluoro-ethanone(2.3g), and potassium carbonate (0.22g) was added and the reaction mixture was stirred at 90 °C under nitrogen for overnight (14 h). The completion of the reaction was monitored by Thin Layer Chromatography (TLC). After the completion of the reaction solvent was evaporated under reduced pressure and the reaction mixture was diluted with ethyl acetate (50 ml), washed with water (2 x 45 ml), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 15 % ethyl acetate and cyclohexane as an eluent.

H NMR (CDCI₃, 400 MHz,) δ: 7.65-7.68 (s, 2H), 7.23-7.38 (m, 4H), 7.14-7.18(m, 2H), 5.81 (t, 1 H), 3.06- 3.08 (m, 1 H), 2.89-2.92 (m, 1 H), 2.50-2.53 (m, 1 H), 2.34-2.37 (m, 1 H), 1.41 (s, 9H), 1.36 (s, 9H).

To a stirring solution of tert-butyl N-tert-butoxycarbonyl-N-[5-[(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but- 2-enoyl]indan-1-yl]carbamate (3g) in tetrahydrofuran( 40ml_) ethyl 2-sulfinylacetate (2g) was added followed by the addition of Ν,Ν,Ν-Triethylamine (0.3g). The reaction mass was stirred at room temperature overnight. The completion of the reaction was monitored by Thin Layer Chromatography (TLC). After completion of the reaction, the reaction mixture was evaporated under reduced pressure, was diluted with ethyl acetate (50 ml), washed with water (25 ml x 2) and dried over sodium sulphate. The combined organic phases were evaporated under reduced pressure and the crude residue was purified by column chromatography using 10 % ethyl acetate and cyclohexane as an eluent.

LCMS (Method A) RT 2.7 min [M+H]⁺ 720.1.

H NMR (CDCI₃, 400 MHz,) δ: 7.54 (s, 2H), 7.13-7.40 (m, 4H), 5.73-5.89 (m, 1 H), 4.71-4.80 (m, 1 H), 4.66 (t, 1 H), 3.99-4.23 (m, 2H), 2.76-3.19 (m, 4H), 2.19-2.57 (m, 2H), 1.31-1.46 (m, 18H), 1.19 (t, 3H).

Preparation of 3-[1-[bis(tert-butoxycarbonyl)amino]indan-5-yl]-5-(3,5-dichlorophenyl)-3-hydroxy-5- (trifluoromethyl)tetrahydrothiophene-2-carboxylic acid

To a stirring solution ethyl 3-[1-[bis(tert-butoxycarbonyl)amino]indan-5-yl]-5-(3,5-dichlorophenyl)-3- hydroxy-5-(trifluoromethyl)tetrahydrothiophene-2-carboxylate (2.5g) in tetrahydrofuran (50 imL), lithium hydroxide solution (0.2g in 10 mL water) was added and the stirring was continued for two hours at room temperature. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was acidified with a solution of hydrochloric acid (2N), extracted with ethyl acetate (35 ml), washed with water (30 mL x 2), dried over sodium sulphate and the solvent was evaporated under reduced pressure. Preparation of tert-butyl N-tert-butoxycarbonyl-N-[5-[3-(3,5-dichlorophenyl)-7-oxo-3- (trifluoromethyl)-6-oxa-2-thiabicyclo[3.2.0]heptan-5-yl]indan-1 -yl]carbamate

To a solution of 3-[1-[bis(tert-butoxycarbonyl)amino]indan-5-yl]-5-(3,5-dichlorophenyl)-3-hydroxy-5- (trifluoromethyl)tetrahydrothiophene-2-carboxylic acid (2g ) in pyridine (5 mL) cooled to 0 °C

methanesulfonyl chloride (0.82g) was added. The reaction was stirred at room temperature overnight. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was acidified with a solution of hydrochloric acid (2N), extracted with ethyl acetate (35 ml), washed with water (30 mL x 2), dried over sodium sulphate and the solvent was evaporated under reduced pressure. The combined organic phases were evaporated under reduced pressure and the crude residue was purified by column chromatography using 10 % ethyl acetate and cyclohexane as an eluent. Preparation of tert -butyl N-tert-butoxycarbonyl-N-[5-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H- thiophen-4-yl]indan-1 -yl]carbamate

To a solution of tert-butyl N-tert-butoxycarbonyl-N-[5-[3-(3,5-dichlorophenyl)-7-oxo-3-(trifluoromethyl)-6- oxa-2-thiabicyclo[3.2.0]heptan-5-yl]indan-1-yl]carbamate (0.6 g) in Dimethylformamide (20 mL), the reaction mixture was stirred at 120 °C for two hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 ml), washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 10 % ethyl acetate and cyclohexane as an eluent.

LCMS (Method A) RT 1.8 min [M+H]⁺ 630.5.

H NMR (CDCI₃, 400 MHz,) δ: 7.43 (s, 2H), 7.36-7.38 (m, 1 H), 7.22-7.26 (m, 1 H), 7.14-7.20 (m, 2H), 6.43 (s, 1 H), 5.78 (t, 1 H), 3.79-3.88 (m, 1 H), 3.63 (d, 1 H), 3.07 (ddd, 1 H), 2.80-2.93 (m, 1 H), 2.49 (ddd, 1 H), 2.24-2.37 (m, 1 H), 1.34-1.41 (m, 18H). Preparation of 5-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]indan-1 -amine

To a solution of tert-butyl N-tert-butoxycarbonyl-N-[5-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H- thiophen-4-yl]indan-1-yl]carbamate (0.2 g) in dichloromethane (5 mL), HCI in dioxane solution (20% solution) was added. The reaction was stirred at 0 °C five hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with toluene and evaporated under reduced pressure.

Preparation of N-[5-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]indan-1 - yl]acetamide [D-1]

To a solution of 5-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]indan-1-am

Hydrochloride (0.2 g) in dichloromethane (5 mL), N,N,N-Triethylamine(0.98g) was added. The reaction was cooled to 0 °C acetyl chloride (0.040g) was added under nitrogen atmosphere and stirring was continued for three hours. The completion of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with dichloromethane (30 ml), washed with water (25 ml, twice), dried over sodium sulphate, evaporated under reduced pressure and purified by column chromatography using 25 % ethyl acetate and cyclohexane as an eluent.

LCMS (Method B) RT 5.34 min [M+H]⁺ 471.91.

1 H NMR (Acetone-d₆, 400 MHz,) : 7.59-7.72 (m, 1 H), 7.43-7.54 (m, 3H), 7.19-7.34 (m, 2H), 7.06-7.16 (m, 1 H), 6.68 (s, 1 H), 5.24 (q, 1 H), 3.85-3.97 (m, 1 H), 3.74-3.82 (m, 1 H), 2.59-2.92 (m, 2H), 2.27-2.48 (m, 1 H), 1.80-1.90 (m, 3H), 1.59-1.79 (m, 1 H).

Preparation of N-[5-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]indan-1 -yl]-2 methyl -propanamide [D-3

LCMS (Method B) RT 5.52 min [M+H]⁺ 499.89.

H NMR (CDCI₃, 400 MHz,) δ: 7.36 (s, 2H), 7.31 (t, 1 H), 7.15 (s, 3H), 6.40 (s, 1 H), 5.35-5.57 (m, 2H), 3.67-3.85 (m, 1 H), 3.58 (d, 1 H), 2.72-3.00 (m, 2H), 2.49-2.63 (m, 1 H), 2.31 (d, 1 H), 1.62-1.82 (m, 1 H), 1.08-1.16 (m, 6H).

Preparation of N-[5-[2-(3,5-dichlorophenyl)-2-(trifluoromethyl)-3H-thiophen-4-yl]indan-1 - yl]cyclopropanecarboxamide [D-2] _„_

-107-

LCMS (Method B) RT 5.37 min [M+H]⁺ 497.86.

1 H NMR (Acetone-d_6, 400 MHz,) : 7.62-7.84 (m, 1 H), 7.50-7.55 (m, 2H), 7.44-7.48 (m, 1 H), 7.23-7.33 (m, 2H), 7.1 1 (d, 1 H), 6.51-6.84 (m, 1 H), 5.14-5.46 (m, 1 H), 3.85-3.96 (m, 1 H), 3.73-3.83 (m, 1 H), 2.60-2.95 (m, 2H), 2.27-2.44 (m, 1 H), 1.66-1.82 (m, 1 H), 1.45-1.59 (m, 1 H), 0.68-0.84 (m, 3H), 0.51-0.66 (m, 2H). Table D. Compounds of formal I-

The following LC-MS methods were used to characterize the compounds:

LC-MS (Liquid Chromatography-Mass Spectrometer) Acquisition (Method A)

Instrumentation

Optimized Mass Parameter

lonisation method Electrospray (ESI)

Polarity positive and Negative Polarity Switch

Scan Type MS2 Scan Capillary (kV) 4.00

Fragmentor (V) 100.00

Gas Temperature (°C) 350

Gas Flow (L/min) 1 1

Nebulizer Gas (psi) 35

Mass range 1 10 to 1000 Da

DAD Wavelength range (nm): 190 to 400

Optimized Chromatographic parameter

Gradient conditions: (Solvent A: Water, 0.1 % formic acid and Solvent B: Acetonitrile, 0.1 % formic acid)

Thermo LC-MS (Liquid Chromatography-Mass Spectrometer) Acquisition (Method B)

Instrumentation:-

Optimized Mass Parameter:

lonisation method Atmospheric Pressure Chemical Ionization (APCI)

Polarity positive and Negative Polarity Switch

Scan Type MS Full Scan

Probe Temperature (°C) 400

Corona (μΑ) 7.00

Detector (V) 1400

Cone (V) 50

Nebulizer Gas (psi) 45

Mass range(Da) 80 to 950 DAD Wavelength range (nm) 210 to 350

Optimized Chromatographic parameter:

Gradient conditions

(Solvent A: Water, 0.05% formic acid and Solvent B: Methanol)

Biological Examples

These Examples illustrate the insecticidal properties of the compounds of formula (I). The tests were performed as follows:

Spodoptera littoralis (Egyptian cotton leaf worm)

Cotton leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality 3 days after infestation.

Fllowing compounds resulted in at least 80% mortality at an application rate of 200 ppm:

A-2, B-1 , B-2, B-3, B-5,C-1 , C-2, C-3,D-1 , D-2, D-3

Plutella xylostella (Diamond back moth):

24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality 5 days after infestation.

The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

A-1 , A-2, A-3, B-1 , B-2, B-3, B-5, C-1 , C-2, C-3, D-1 , D-2, D-3

Diabrotica balteata, (Corn rootworm)

Maize sprouts, placed on an agar layer in 24-well microtiter plates were treated with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions by spraying. After drying, the plates were infested with L2 larvae (6 to 10 per well). The samples were assessed for mortality 4 days after infestation.

A-1 , A-2, A-3, B-1 , B-2, B-3, B-4, B-5, C-1 , C-2, C-3, D-1 , D-2, D-3

Thrips tabaci (Onion thrips):

Sunflower leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying the leaf discs were infested with a thrips population of mixed ages. The samples were assessed for mortality 6 days after infestation.

B-1 , B-2, B-3, B-5, C-1 , C-2, C-3, D-1

Tetranychus urticae (Two-spotted spider mite):

Bean leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10Ό00 ppm DMSO stock solutions. After drying the leaf discs were infested with a mite population of mixed ages. The samples were assessed for mortality on mixed population (mobile stages) 8 days after infestation.

A-1 , A-2, B-1 , B-2, B-3, B-5, C-1 , C-2, C-3, D-1 , D-3

Claims

Claims: compound of formula I

P is selected from P1 and P2, or P and A¹ = C-R⁵ together are P3

P1 P2 P3

G is oxygen or sulfur;

G² is oxygen or sulfur;

G³ is oxygen or sulfur;

R is hydrogen, Ci-C₈alkyl, d-C₈alkoxy, Ci-C₈alkylcarbonyl, or Ci-C₈alkoxycarbonyl;

R² is Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃-Ci₀cycloalkyl substituted by one to five R ³, C₃-Ci₀cycloalkyl-Ci-C₄alkylene or C₃-Ci₀cycloalkyl-Ci-C₄alkylene substituted by one to five R ³, aryl-Ci-C₄alkylene- or aryl-Ci-C₄alkylene- substituted by one to five R ⁴, heterocyclyl-Ci-C₄alkylene- or heterocyclyl-Ci-C₄alkylene- substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴, d-

C₈alkylaminocarbonyl-Ci-C₄alkylene, Ci-C₈haloalkylaminocarbonyl-Ci-C₄alkylene, C₃-C₈cycloalkyl- aminocarbonyl-Ci-C₄ alkylene, aryl-CH₂-aminocarbonyl-Ci-C₄alkylene or aryl-CH₂-aminocarbonyl-Ci- C₄alkylene wherein the aryl is substituted by one to five R ⁴, Ci-C₈alkylaminocarbonyl, d- C₈haloalkylaminocarbonyl, C₃-C₆cycloalkylaminocarbonyl,

or d-C₆haloalkyl-0- N=CH-;

R³ is d-Cshaloalkyl;

each R⁵ is independently hydrogen, halogen, cyano, nitro, d-dalkyl, d-C₈haloalkyl, d- dalkenyl, d-dhaloalkenyl, C₂-C₈alkynyl, d-dhaloalkynyl, d-docycloalkyl, d-dalkoxy, d- C₈haloalkoxy, d-dalkylthio, d-dhaloalkylthio, d-dalkylsulfinyl, d-dhaloalkylsulfinyl, d- C₈alkylsulfonyl, or Ci-C₈haloalkylsulfonyl, or two R⁵ on adjacent carbon atoms together form a -CH=CH- CH=CH- bridge or a -N=CH-CH=CH- bridge;

R^6a and R^6b are each independently hydrogen, halogen, cyano, Ci-C₈alkyl, Ci-C₈haloalkyl, or C₃- C₈cycloalkyl, or R^6a and R^6b together with the carbon atom to which they are attached may form a 3 to 6- membered carbocyclic ring;

R⁸ is Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃-Ci₀cycloalkyl substituted by one to five R ³, C₃-Ci₀cycloalkyl-Ci-C₄alkylene or C₃-Ci₀cycloalkyl-Ci-C₄alkylene substituted by one to five R ³, aryl-Ci-C₄alkylene- or aryl-Ci-C₄alkylene- substituted by one to five R ⁴, heterocyclyl-Ci-C₄alkylene- or heterocyclyl-Ci-C₄alkylene- substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, or heterocyclyl or heterocyclyl substituted by one to five R ⁴, each R⁹ is independently hydrogen, Ci-C₈alkyl, Ci-C₈alkoxy, CrC₈alkylcarbonyl, or Ci-C₈alkoxycarbonyl;

each R is independently halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, C₂-C₈alkenyl, C₂- C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, hydroxy, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, Ci- Cshaloalkylsulfonyl, Ci-C₈alkylcarbonyl, or d-C₈alkoxycarbonyl;

each R ² is independently halogen, cyano, nitro, hydroxy, amino, Ci-C₈alkylamino, (d- C₈alkyl)₂amino, Ci-C₈alkylcarbonylamino, Ci-C₈haloalkylcarbonylamino, Ci-C₈alkoxy, Ci-C₈haloalkoxy, aryloxy or aryloxy substituted by one to five R ⁶, aryloxy-Ci-C₄alkylene or aryloxy-Ci-C₄alkylene wherein the aryl moiety is substituted by one to five R ⁶, Ci-C₈alkylcarbonyl, Ci-C₈alkoxycarbonyl, mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, Ci- Cshaloalkylsulfonyl, aryl-Ci-C₄alkylthio or aryl-Ci-C₄alkylthio wherein the aryl moiety is substituted by one to five R ⁶;

each R ³ is independently halogen, cyano, d-C₈alkyl, C₂-C₈alkenyl, C₂-C₈alkynyl, or Ci-C₈alkoxy, Ci-C₈akoxycarbonyl, or two R ³ are together R ⁹-0-N=;

each R ⁴ is independently halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, Ci-C₈cyanoalkyl, C₂- C₈alkenyl, C₂-C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, C₃-Ci₀cycloalkyl, C₃-Ci₀cycloalkyl-Ci- C₄alkylene, hydroxy, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, Ci-C₈alkylthio, Ci-C₈haloalkylthio, Ci- C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, Ci-C₈haloalkylsulfonyl, Ci-C₈alkylaminosulfonyl, (Ci-C₈alkyl)₂aminosulfonyl, Ci-C₈alkylcarbonyl, Ci-C₈haloalkylcarbonyl, Ci-C₈alkoxycarbonyl,

Cshaloalkoxycarbonyl, aryl or aryl substituted by one to five R ⁶, heterocyclyl or heterocyclyl substituted by one to five R ⁶, aryl-Ci-C₄alkylene or aryl-Ci-C₄alkylene wherein the aryl moiety is substituted by one to five R ⁶, heterocyclyl-Ci-C₄alkylene or heterocyclyl-Ci-C₄alkylene wherein the heterocyclyl moiety is substituted by one to five R ⁶, aryloxy or aryloxy substituted by one to five R ⁶, or aryloxy-Ci-C₄alkylene or aryloxy-Ci-C₄alkylene wherein the aryl moiety is substituted by one to five R ⁶ or two R ⁴ are together =0; each R ⁵ is independently halogen, cyano, nitro, Ci-C₈alkyl, Ci-C₈haloalkyl, C₂-C₈alkenyl, C₂- C₈haloalkenyl, C₂-C₈alkynyl, C₂-C₈haloalkynyl, hydroxy, Ci-C₈alkoxy, Ci-C₈haloalkoxy, mercapto, d- C₈alkylthio, Ci-C₈haloalkylthio, Ci-C₈alkylsulfinyl, Ci-C₈haloalkylsulfinyl, Ci-C₈alkylsulfonyl, d- C₈haloalkylsulfonyl, Ci-C₈alkylcarbonyl, or Ci-C₈alkoxycarbonyl;

each R ⁶ is independently halogen, cyano, nitro, Ci-C₄alkyl, Ci-C₄haloalkyl, d-C₄alkoxy, or d-

C₄haloalkoxy;

each R ⁹ is hydrogen, Ci-C₈alkyl or Ci-C₈haloalkyl;

n is 1 or 2;

p is 0, 1 , 2, 3, 4, or 5;

or a salt or A/-oxide thereof.

2. A compound according to claim 1 , wherein A¹ = C-R^5b and R^5b is halogen or methyl.

3. A compound according to claim 1 or claim 2, wherein R² is Ci-C₈alkyl or Ci-C₈alkyl substituted by one to five R ², C₃-Ci₀cycloalkyl or C₃-Ci₀cycloalkyl substituted by one to five R ³, C₃-Ci₀cycloalkyl- C(R ⁷)(R¹⁸)- or C₃-C₁₀cycloalkyl-C(R ⁷)(R¹⁸)- wherein the cycloalkyi is substituted by one to five R ³, aryl- C(R ⁷)(R¹⁸)- or aryl-C(R ⁷)(R¹⁸)- wherein the aryl is substituted by one to five R ⁴, heterocyclyl-

C(R ⁷)(R¹⁸)- or heterocyclyl-C(R ⁷)(R¹⁸)- wherein the heterocyclyl is substituted by one to five R ⁴, aryl or aryl substituted by one to five R ⁴, heterocyclyl or heterocyclyl substituted by one to five R ⁴, d- C₈alkylaminocarbonyl-CH₂-, Ci-C₈haloalkylaminocarbonyl-CH₂-, C₃-C₈cycloalkylaminocarbonyl-CH₂-, aryl-CH₂-aminocarbonyl-CH₂- or aryl-CH₂-aminocarbonyl-CH₂- wherein the aryl is substituted by one to five R ⁴, Ci-C₈alkylaminocarbonyl, Ci-C₈haloalkylaminocarbonyl, C₃-C₆cycloalkylaminocarbonyl, d- C₆alkyl-0-N=CH-, or C₁-C₆haloalkyl-0-N=CH-;

wherein heterocyclyl is a 4 to 7-membered heterocyclic ring containing one to three heteroatoms independently selected from O, S, SO, S0₂, N, and N(R²⁰) as ring atoms,

wherein aryl is phenyl;

wherein R ⁷ and R ⁸ are independently hydrogen, cyano, halogen, Ci-C₄alkyl, Ci-C₄haloalkyl, d- dalkoxy, d-dhaloalkoxy or C₃-C₆cycloalkyl;

or R ⁷ and R ⁸ together form a three to six membered carbocycle;

and wherein R²⁰ is hydrogen or R ⁴.

4. A compound according to any one of claims 1 to 3, wherein A¹ is C-R⁵, A² is CH, A³ is CH and A⁴ is CH or A² is CH, A³ is CH and A⁴ is CH and P and A¹ = C-R⁵ together are P3 or P_.

5. A compound according to any one of claims 1 to 4, wherein R³ is chlorodifluoromethyl or trifluoromethyl.

6. A compound according to any one of claims 1 to 5, wherein R⁴ is group (C)

wherein X² is C-X⁶ or nitrogen (preferably C-X⁶); X¹, X³ and X⁶ ar ee iinncdependently hydrogen, halogen or trihalomethyl, e.g. wherein at least two of X¹, X³ and X⁶ are not hydrogen.

7. A compound according to claim 1 , wherein A¹ is C-R^5b; A², A³ and A⁴ are C-H; G is oxygen; R² is d-C₄alkyl or d-C₄alkyl substituted by one to five halogen, C₃-C₆cycloalkyl or C₃- C₆cycloalkyl substituted by one to five groups independently selected from halogen, methyl and halomethyl, C₃-C₆cycloalkyl-methylene or C₃-C₆cycloalkyl-methylene substituted by one to five groups independently selected from halogen, methyl and halomethyl C₂-C₄alkenyl or C₂-C₄alkenyl substituted by one to five halogen, C₂-C₄alkynyl or C₂-C₄alkynyl substituted by one to five halogen; R³ is

chlorodifluoromethyl or trifluoromethyl; R⁴ is group (C)

wherein X² is C-X⁶ or nitrogen (preferably C-X⁶); X¹, X³ and X^D are independently hydrogen, halogen or trihalomethyl, e.g. wherein at least two of X¹, X³ and X⁶ are not hydrogen..

8. A compound according to claim 7, wherein A¹ is C-R^5b; A², A³ and A⁴ are C-H; G is oxygen; R² is ethyl, propyl, butyl, fluoroethyl, fluoropropyl, fluorobutyl, difluoroethyl, difluoropropyl, difluorobutyl, trifluoroethyl, trifluoropropyl, trifluorobutyl, cyclopropyl, cyclobutyl, cyclopropylmethylene,

cyclobutylmethylene, allyl or propargyl; R³ is chlorodifluoromethyl or trifluoromethyl; R⁴ is group A1 , wherein X is C-R ² and each R ² is independently hydrogen, halogen or trihalomethyl, wherein at least two R ² are not hydrogen; R^5b is chloro, bromo or methyl.

P1 P2 P3 wherein A¹ , A², A³, A⁴, G¹, G², G³, R¹ , R², R³, R⁴, R⁵, R^6a, R^6b, R⁷, R⁸, R⁹ , R¹⁰ , R¹¹ and p and n are as defined in any one of claims 1 to 7, and wherein the molar proportion of the compound of formula I** compared to the total amount of both the compound of formula and II* is greater than 50%.

10. A mixture according to claim 9, wherein A¹ , A², A³, A⁴, G , G², G³, R¹ , R², R³, R⁴, R⁵, R^6a, R' R⁷, R⁸, R⁹ , R ⁰ , R and p and n are as defined in claim 7, and wherein the molar proportion of the compound of formula I** compared to the total amount of both the compound of formula and I** is greater than 70%.

1 1. A mixture according to claim 9, wherein A¹ , A², A³, A⁴, G , G², G³, R¹ , R², R³, R⁴, R⁵, R^6a, R' R⁷, R⁸, R⁹ , R ⁰ , R and p and n are as defined in claim 8, and wherein the molar proportion of the compound of formula I** compared to the total amount of both the compound of formula and I** is greater than 70%.

12. A compound of formula Int-I

wherein A¹ , A², A³, A⁴, R³ and R⁴ are as defined for the compound of formula I in any one of claims 1 to 8, or a salt or N-oxide thereof; or

a compound of formula Int-I I

wherein A¹ , A², A³, A⁴, R³, R⁴, G and n are as defined for the compound of formula I in any one of claims 1 to 8, and R is OH, d-C₆alkoxy, CI, F or Br or a salt or N-oxide thereof; or a compound of formula Int-lll

wherein A¹, A², A³, A⁴, R³ and R⁴ are as defined for the compound of formula I in any one of claims 1 to 8, R is Ci-C₆alkyl or Ci-C₆alkyl optionally substituted by aryl, or a salt or N-oxide thereof.

13. An insecticidal, acaricidal, nematicidal or molluscicidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 11 and optionally at least one additional compound having biological activity.

10 14. A combination product comprising a pesticidally effective amount of a component A and a

pesticidally effective amount of component B, wherein component A is a compound of formula (I) as defined in any one of claims 1 to 11 , and component B is at least one compound selected from the group consisting of imidacloprid, enrofloxacin, praziquantel, pyrantel embonate, febantel, penethamate, moloxicam, cefalexin, kanamycin, pimobendan, clenbuterol, fipronil, ivermectin, omeprazole, tiamulin,

15 benazepril, milbemycin, cyromazine, thiamethoxam, pyriprole, deltamethrin, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, selamectin, carprofen, metaflumizone, moxidectin, methoprene (including S-methoprene), clorsulon, pyrantel, amitraz, triclabendazole, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, nemadectin, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, tetramisole,

20 levamisole, pyrantel pamoate, oxantel, morantel, triclabendazole, epsiprantel, fipronil, lufenuron,

ecdysone and tebufenozide.