EA040613B1 - HERBICIDE COMPOUNDS - Google Patents

Description

The present invention relates to herbicidal substituted phenylpyridazinones and substituted phenylpyridazinone derivatives of formula (I), as well as to methods and intermediates used to obtain such derivatives. The present invention further extends to herbicidal compositions containing such derivatives, as well as to the use of such compounds and compositions in providing control of the growth of unwanted plants, in particular to the use in providing control of weeds, such as broadleaf dicotyledonous weeds, in crops of useful plants.

Herbicidal pyridazinones are known from WO 2009/086041. In addition, herbicidal 5/6-membered heterocyclyl-substituted pyridazinones are known from WO 2011/045271. However, WO 2013/160126 describes indolylpyridazinone derivatives which exhibit herbicidal activity.

The present invention is based on the discovery that substituted phenylpyridazinones and substituted phenylpyridazinone derivatives of formula (I) exhibit surprisingly good herbicidal activity.

Thus, in a first aspect, a compound of formula (I) is provided

or its salt, or N-oxide, where

R ¹ is selected from the group consisting of methyl, ethyl, n-propyl, cyclopropyl, propargyl, or C ₁ haloalkyl;

R ² is selected from the group consisting of hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloαalkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₃ -αlkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ cycloαalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ -αkynyl and C ₂ -C ₆ haloalkynyl;

G is hydrogen or C(O)R ³ ;

R ³ is selected from the group consisting of C ₁ -C ₆ -αkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ -alkyl-S-, C ₁ -C ₆ -αlkoxy , -NR ⁴ R ⁵ and phenyl optionally substituted with one or more R ⁶ ;

R ⁴ and R ⁵ are independently selected from the group consisting of C ₁ -C ₆ alkyl and C ₁ -C ₆ alkoxy, or R ⁴ and R ⁵ together may form a morpholinyl ring;

R ⁶ is selected from the group consisting of halogen, cyano, nitro, C ₁ -C ₃ -alkyl, C ₁ -C ₃ -haloalkyl, C ₁ -C ₃ -alkoxy and C ₁ -C ₃ -haloalkoxy, each of X and Y independently represents hydrogen, C ₁ -C ₃ -alkyl, C ₁ -C ₃ -haloalkyl or halogen;

D is a substituted or unsubstituted 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, and when D is substituted, it is substituted on at least one atom ring carbon with R ⁸ and/or ring nitrogen with R ⁹ ;

each R ⁸ is independently oxygen, hydroxyl, halogen, cyano, C ₁ -C ₆ -alkyl, C 1 -C ₆ haloalkyl, C ₁ -C 6 -haloalkoxy, C ₁ -C ₃ -haloalkoxy-C ₁ -C ₃ -alkyl- , C ₁ -C ₆ -alkoxy, C ₁ -C ₃ -alkoxyC ₁ -C ₃ -αkyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl-, C ₃ -C ₆ -cycloalkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ -hydroxyalkyl-, C ₁ -C ₆ -alkylcarbonyl-, C ₁ - C ₆ -alkyl-S (O) _m -, amino, C ₁ -C ₆ -alkylamino, C ₁ -C ₆ -dialkylamino, -C (C ₁ -C ₃ -alkyl) \u003d N-O-C ₁ -C ₃ -alkyl and C ₂ -C ₆ haloalkynyl;

m is an integer equal to 0, 1 or 2; and each R ⁹ is independently C ₁ -C ₄ -alkyl, C ₃ -C ₆ -alkoxy, C ₁ -C ₂ -alkoxy-C ₁ -C ₂ -alkyl, C ₂ -C ₄ -alkenyl, C ₁ - C ₄ haloalkyl, C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ alkynyl or C ₂ -C ₄ haloalkynyl; or

D is a substituted or unsubstituted phenyl ring (Dp)

where p denotes the point of attachment (Dp) to the rest of the molecule;

each of Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ is independently selected from the group consisting of hydrogen, cyano, amino, C ₁ -C ₃ -dialkylamino, hydroxy, C ₁ -C ₃ -alkyl, C ₁ - C ₄ alkoxy, C ₁ -C ₃ haloalkyl, C ₁ -C ₃ haloalkoxy and halogen; And

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W is either where a is the point of attachment to the phenylpyridazinone/phenylpyridazinedione moiety;

b denotes the point of attachment to the ring D;

each of R ¹⁰ , R ¹² , R ¹⁴ and R ¹⁵ independently represents hydrogen;

each of R ¹¹ and R ¹³ independently represents hydrogen.

The compounds of formula (I) may contain asymmetric centers and may be present as a single enantiomer, pairs of enantiomers in any proportion or, if more than one asymmetric center is present, contain diastereoisomers in all possible ratios. As a rule, one of the enantiomers is characterized by increased biological activity compared to other variants.

Similarly, in the case of disubstituted alkenes, they may be present in the E or Z form, or as mixtures of both in any proportion.

Moreover, the compounds of formula (I) may be in equilibrium with alternative tautomeric forms. For example, a compound of formula (Ii), i.e. a compound of formula (I) wherein R ² is hydrogen and G is hydrogen may be represented in at least three tautomeric forms

(l-i)

It should be understood that all tautomeric forms (individual tautomer or mixtures thereof), racemic mixtures and individual isomers are within the scope of the present invention.

Each alkyl moiety, either by itself or as part of a larger group (such as alkoxy, alkylthio, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl, etc.) may be straight chain or branched. Generally, alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, neopentyl or n-hexyl. Alkyl groups are usually C ₁ -C ₆ alkyl groups (except where already defined more narrowly), but are preferably C ₁ -C ₄ alkyl or C ₁ -C ₃ alkyl groups, and more preferably are C ₁ -C ₂ -alkyl groups (such as methyl).

The alkenyl and alkynyl moieties may be in straight or branched chain form, and the alkenyl moieties may be in either the (E)- or ^-configuration if desired. Alkenyl or alkynyl moieties are typically C ₂ -C ₄ alkenyl or C ₂ -C ₄ alkynyl, more specifically vinyl, allyl, ethynyl, propargyl or prop-1-ynyl. Alkenyl and alkynyl fragments may contain one or more double and/or triple bonds in any combination; but preferably they contain only one double bond (for alkenyl) or only one triple bond (for alkynyl).

Preferably the term cycloalkyl refers to cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

In the context of the present description, the term aryl preferably means phenyl. The term heteroaryl as used herein means an aromatic ring system containing at least one heteroatom in the ring and consisting of a single ring. Single rings will preferably contain 1, 2 or 3 ring heteroatoms independently selected from nitrogen, oxygen and sulfur. Typically, heteroaryl is furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1, 3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl.

Heterocyclyl groups and heterocyclic rings (either by themselves or as part of a larger group such as heterocyclyl-alkyl-) are ring systems containing at least one heteroatom and may be in mono- or bicyclic form. Heterocyclyl groups will preferably contain up to two heteroatoms, which will preferably be selected from nitrogen, oxygen and sulfur. Examples of heterocyclic groups include oxetanyl, thietanyl, azetidinyl and 7-oxa-bicyclo[2.2.1]hept-2-yl. Heterocyclyl groups containing one acid atom

- 2 040613 kind as a heteroatom are most preferred. Heterocyclyl groups are preferably 3-8 membered, more preferably 3-6 membered rings.

Halogen (or halo) encompasses fluorine, chlorine, bromine, or iodine. The same applies accordingly to halogen in the context of other definitions such as haloalkyl or halophenyl.

Haloalkyl groups with a chain length of 1 to 6 carbon atoms are, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro -2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl, heptafluoro-n-propyl and perfluoro-n-hexyl.

Alkoxy groups are preferably characterized by a chain length of 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy or an isomer of pentyloxy or hexyloxy, preferably methoxy and ethoxy. It should also be understood that two alkoxy substituents may be present on the same carbon atom.

Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy or 2,2,2- trichloroethoxy, preferably difluoromethoxy, 2-chloroethoxy or trifluoromethoxy.

C ₁ -C ₆ -alkyl-S- (alkylthio) is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio.

C ₁ -C ₆ -alkyl-S(O)-(alkylsulfinyl) is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl.

C ₁ -C ₆ -alkyl-S(O) ₂ - (alkylsulfonyl) is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.

Group Q

G O

^R (Q) is referred to herein as the pyridazinedione/pyridazinone moiety, where B is the point of attachment to the rest of the molecule (ie, the optionally substituted phenyl-WD moiety).

The present invention also includes the agriculturally acceptable salts that the compounds of formula (I) can form with amines (eg ammonia, dimethylamine and triethylamine), alkali metal and alkaline earth metal bases or quaternary ammonium bases. Among hydroxides, oxides, alkoxides, and hydrocarbonates and carbonates of alkali metals and alkaline earth metals used as salt formers, special attention should be paid to hydroxides, alkoxides, oxides and carbonates of lithium, sodium, potassium, magnesium and calcium, but especially hydroxides, alkoxides, oxides and carbonates of sodium, magnesium and calcium. The corresponding trimethylsulfonium salt can also be used. The compounds of formula (I) according to the present invention also include hydrates which may be formed during salt formation.

Preferred values R ¹ , R ² , R ³ , R ⁴ , R ^{5 , R 6 ,} R ⁸ , R ⁹ , R 10 , ^{R 11 , R 12 , R 13 , R 14 , R 15 , W , D ,} Dp, G, X, Y, Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and m are set forth below, and the compound of formula (I) in accordance with the present invention may include any combination of these values. One skilled in the art will appreciate that the values for any specified group of embodiments may be combined with the values for any other group of embodiments, unless such combinations are mutually exclusive.

Preferably R ¹ is selected from the group consisting of methyl, ethyl, propyl (particularly n- or cyclopropyl), propargyl or C1-haloalkyl. More preferably R ¹ is methyl, ethyl, cyclopropyl, propargyl or C1-fluoroalkyl. Even more preferably R ¹ is methyl, ethyl, cyclopropyl or propargyl.

Preferably R ² is selected from the group consisting of hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₃ alkoxy-C ₁ -C ₃ -alkyl , C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl and C ₂ -C ₆ haloαkynyl. More preferably R ² is selected from the group consisting of methyl, ethyl, cyclopropyl, trifluoromethyl and methoxymethyl, even more preferably cyclopropyl, trifluoromethyl or methyl, most preferably cyclopropyl or methyl. In one group of embodiments of the present invention, R ² is hydrogen. Additional

- 3 040613 group of embodiments R ² is cyclopropyl, in the third group of embodiments R ² is methyl, and in the fourth group of embodiments R ² is trifluoromethyl.

As described herein, G may be hydrogen or -C(O)-R ³ and R ³ is selected from the group consisting of C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1- C6-alkyl-S-, C1-C6-alkoxy, -NR ⁴ R ⁵ and phenyl optionally substituted with one or more R ⁶ . As defined herein, R ⁴ and R ⁵ are independently selected from the group consisting of C1-C ₆ -alkyl, Cl-C ₆ -alkoxy-; or they can together form a morpholinyl ring. Preferably, R ⁴ and R ⁵ are each independently selected from the group consisting of methyl, ethyl, propyl, methoxy, ethoxy and propoxy. R ⁶ is selected from the group consisting of halo, cyano, nitro, Cl-C ₃ alkyl, Cl-C ₃ haloalkyl, Cl-C ₃ alkoxy, and C ₁ -C ₃ haloalkoxy.

Preferably R ³ is C ₁ -C ₄ alkyl, C ₂ -C ₃ alkenyl, C ₂ -C ₃ alkynyl, -C ₁ -C ₄ alkoxy, -NR ⁴ R ⁵ where R ⁴ and R ⁵ together form a morpholinyl ring, or phenyl. More preferably R ³ is isopropyl, t-butyl, methyl, ethyl, propargyl, t-butoxy or methoxy. More preferably R ³ is isopropyl, t-butyl, methyl, ethyl, propargyl or methoxy.

In one group of embodiments, G is hydrogen or -C(O)-R ³ where R ³ is C ₁ -C ₄ alkyl, C ₂ -C ₃ alkenyl, C ₂ -C ₃ alkynyl, or -C ₁ -C ₄ -alkoxy. In an additional group of embodiments, G is hydrogen or -C(O)-R ³ where R ³ is isopropyl, t-butyl, methyl, ethyl, propargyl, or methoxy. However, it is especially preferred that G is hydrogen or -C(O)-R ³ where R ³ is isopropyl.

X is preferably hydrogen, halogen or C ₁ -haloalkyl, more preferably hydrogen, fluorine, chlorine, bromine or C ₁ -fluoroalkyl and even more preferably hydrogen, fluorine, chlorine or trifluoromethyl. In one group of embodiments, it is preferred that X is ortho to the pyridazinone/pyridazinedione moiety (Group Q). It is particularly preferred that X is fluorine, chlorine or C ₁ -haloalkyl (in particular C ₁ -fluoroalkyl) and is in the ortho position relative to the pyridazinone/pyridazinedione moiety (Group Q).

Y preferably represents hydrogen, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl or halogen. More preferably Y is hydrogen, chlorine, fluorine or bromine.

In one group of embodiments, Y is preferably in an ortho position relative to the -W-D fragment. In an additional group of embodiments, Y is para to the pyridazinone/pyridazinedione moiety (Group Q).

It is particularly preferred that Y is ortho to the -W-D moiety and is a halogen, in particular chlorine or fluorine; more preferably chlorine.

As described herein, D is a substituted or unsubstituted phenyl ring (Dp) or is a substituted or unsubstituted 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, and wherein, if D is a substituted heteroaryl ring, it is substituted on at least one carbon atom in the ring with R ⁸ and/or on a nitrogen atom in the ring with R ⁹ . When D is a substituted or unsubstituted 5- or 6-membered monocyclic heteroaryl ring, it is preferably substituted (as described herein) or unsubstituted furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1, 3,5-triazinyl ring.

In such embodiments, D is preferably a substituted (as described herein) or unsubstituted pyridyl, pyrazolyl, thiazolyl, pyrimidinyl, thienyl, triazolyl, or oxadiazolyl ring, and more preferably a pyridyl ring.

In one group of embodiments, D is a substituted (as described herein) or unsubstituted pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, or pyrazinyl ring.

In an additional group of such embodiments, D is a substituted (as described herein) or unsubstituted oxazolyl, thiazolyl, or pyridyl ring. In some embodiments, D is a substituted or unsubstituted pyridyl ring or a substituted or unsubstituted thiazolyl ring.

If D is substituted, it is preferably substituted with 1 or 2 R ⁸ and/or 1 R ⁹ , more preferably 1 or 2 R ⁸ . When D is a 5-membered substituted heteroaryl ring, it is most preferably substituted with 1 R ⁸ .

Preferably each R ⁸ is independently oxo, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, halogen, cyano, amino, -NHC(O)CH ₃ , hydroxyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ -alkylthio. More prefer

Each R ⁸ is independently oxo, C1-C4 alkyl, C1-C4 haloalkyl, halogen, cyano, hydroxyl, C1-C4 alkoxy or C1-C4 alkylthio, most preferably each R ⁸ is independently halogen or C1- _C4 haloalkyl.

Preferably, each R ⁹ is independently C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, hydroxyl, C ₁ -C ₄ alkoxy, or C ₁ -C ₄ alkylthio.

In specific embodiments, if D is a substituted or unsubstituted 5- or 6-membered monocyclic heteroaryl ring as described above, then D is selected from the group consisting of 4-chloro-3-pyridyl, 4-trifluoromethylpyridyl, 3-pyridyl, and 2-chlorothiazo-5-yl, 2-chloro-3-pyridyl, 3-chloro-4-pyridyl, 1-methyl-3-(trifluoromethyl)-pyrazol-4-yl, thiazol-2-yl, thiazol-5-yl, pyrimidin-5-yl, 4-(tert-butoxy)phenyl, 2-chloro-4-pyridyl, 2-methyl-4-pyridyl, 2-trifluoromethyl-4pyridyl, 4-pyridyl, 2-amino-4-pyridyl, thiophene -3-yl, 1-methylpyrazol-4-yl, 2-methyltriazol-4-yl, 5-methyl-1,3,4-oxadiazol-2-yl, 5-methyl-3-pyridyl, 5-methyl-2 -pyridyl, 6-methyl-2-pyridyl, 3-methyl2-pyridyl, 6-chloro-3-pyridyl, 3-trifluoromethyl-3-pyridyl, 4-methyl-2-pyridyl, 2-acetamidothiazol-5yl, 2-fluoro -4-pyridyl; and 2-trifluoromethyl-3-pyridyl. In a subset of these embodiments, D is selected from the group consisting of 4-chloro-3-pyridyl, 4-trifluoromethylpyridyl, 3-pyridyl and 2-chlorothiazo-5-yl, 2-chloro-3-pyridyl, 3-chloro-4- pyridyl, 1-methyl-3-(trifluoromethyl)-pyrazol-4-yl, thiazol-2-yl, thiazol-5-yl, pyrimidin-5-yl, 4-(tert-butoxy)phenyl, 2-chloro-4 -pyridyl, 2-methyl-4-pyridyl, 2-trifluoromethyl-4-pyridyl, 4-pyridyl, thiophen-3-yl, 5-methyl-3-pyridyl, 5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 3 -trifluoromethyl-3-pyridyl, 2-fluoro-4-pyridyl and 2-trifluoromethyl-3-pyridyl. In a further subgroup of these embodiments, D is selected from the group consisting of 4-chloro-3-pyridyl, 4-trifluoromethylpyridyl, 3-pyridyl, and 2-chlorothiazo-5-yl.

However, as also stated above, D may alternatively be a substituted or unsubstituted phenyl ring (Dp) wherein Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are each independently selected from the group consisting of hydrogen, cyano , amino, C1- _C3 dialkylamino, hydroxy, C1- _C3 alkyl, C1- _C4 alkoxy, C1- _C3 haloalkyl, C1- _C3 haloalkoxy and halogen, and p is the point of attachment to the rest parts of a molecule.

In one group of embodiments, Z ¹ , Z ² , Z ³ , Z ^{4 ,} and Z ⁵ are each independently selected from hydrogen, cyano, C1- _C3 alkyl, C1- _C4 alkoxy, C1- _C3 haloalkyl, C1 -C ₃ -haloalkoxy or halogen. Preferably, Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are each independently selected from hydrogen, cyano, halogen (particularly chlorine or fluorine), methyl, methoxy and trifluoromethyl.

In yet another group of embodiments, each of Z ¹ , Z ² , Z ⁴ and Z ⁵ is hydrogen and Z ³ is not hydrogen. Preferably, in this group of embodiments, Z ³ is halogen, more preferably chlorine.

In yet another group of embodiments, each of Z ¹ , Z ⁴ and Z ⁵ is hydrogen, and Z ² and Z ³ are not hydrogen. In this group of embodiments, it is particularly preferred that Z ² and Z ³ are each independently halogen, and more preferably both of Z ² and Z ³ are chlorine.

In one particularly preferred group of embodiments, all of Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ contain hydrogen.

In additional embodiments, if D is Dp, then Dp is selected from the group consisting of 4-chlorophenyl, 4-trifluoromethylphenyl, 4-cyanophenyl, 4-fluorophenyl, 3,4-difluorophenyl, 2-trifluoromethylphenyl, and 4-tolyl.

W functions as a linker moiety linking the D ring to the rest of the molecule (ie, the phenylpyridazinone/phenylpyridazinedione moiety). Compounds of formula (I) where the linker is W1 have herbicidal activity, while compounds of formula (I) where the linker is W2 may not only have herbicidal activity, but also be useful intermediates in the preparation of compounds of formula (I) containing Wl-linkers. Thus, in the first group of embodiments, W is W1, while in the second group of embodiments, W is W2. In a third group of embodiments, W is -C=C-.

Preferably, R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each hydrogen.

Preferably, R ¹⁴ and R ¹⁵ are each hydrogen.

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I I

Specific examples of W include -CH2-CH2- and -CH=CH-, cis-L and trans-~, and -C=C-. In more preferred embodiments, W is either -CH2-CH2- or -CH=CH (particularly (E)-CH=CH-), even more preferably -CH2-CH2-.

In table. 1 below are 1656 specific examples of compounds of formula (I) according to the present invention.

Table 1

Herbicidal Compounds of the Present Invention

connection no. ^{R1 R2} G X Y w D 1.0001 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - -Ph 1.0002 -Me -Me -H 6-F 3-C1 (E) -CH=CH- -Ph 1.0003 -Me -Me -H 6-F 3-C1 trans- r HC / \ H ₂ C—CH -Ph 1.0004 -Me -Me -H 6-F 3-C1 cis- T H c H ₂ C-CH -Ph 1.0005 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - -Ph 1.0006 -Me -Me -H 6-C1 3-C1 trans-TH c H ₂ C-CH -Ph 1.0007 -Me -Me -H 6-C1 3-C1 cis- T H c H ₂ C-CH -Ph 1.0008 -CH ₂ -C=CH -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - -Ph 1.0009 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - -Ph 1.0010 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - -Ph 1.0011 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - -Ph 1.0012 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0013 -CII _rC =CII -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0014 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0015 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0016 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0017 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0018 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0019 -CII, -C-CH -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0020 cycloprop -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl-

- 6 040613

IL 1.0021 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0022 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0023 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0024 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0025 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0026 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0027 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0028 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0029 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0030 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0031 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0032 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0033 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0034 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0035 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0036 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0037 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0038 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0039 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0040 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0041 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0042 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0043 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0044 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0045 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0046 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0047 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0048 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0049 -cu ₂ -c=cu -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0050 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0051 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0052 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0053 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0054 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0055 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0056 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0057 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0058 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-pyridyl-

-7 040613

1.0059 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0060 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0061 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0062 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0063 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0064 -SP,-S=SP -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0065 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0066 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0067 -SP,-S=SP -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0068 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0069 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0070 -SP,-S=SP -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0071 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0072 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0073 -sp, -s=sp -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0074 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0075 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0076 -SP,-S=SP -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0077 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0078 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - -Ph 1.0079 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- -Ph 1.0080 -Me -Me -(C=O)‘Pr 6-F 3-C1 trans-TH c H ₂ C-CH 1 -Ph 1.0081 -Me -Me -(C=O)*Pr 6-F 3-C1 cis-TH c H ₂ c-CH 1 -Ph 1.0082 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - -Ph 1.0083 -Me -Me -(C=O)‘Pr 6-C1 3-C1 trans- r H c H ₂ C-CH 1 -Ph 1.0084 -Me -Me -(C=O)‘Pr 6-C1 3-C1 cis-THC H ₂ c-CH 1 -Ph 1.0085 -CH ₂ -C=CH -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - -Ph

- 8 040613

1.0086 cycloprop silt -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - -Ph 1.0087 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - -Ph 1.0088 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - -Ph 1.0089 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0090 -CH ₂ -C=CH -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0091 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0092 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0093 -SP ₂ -C=SP -Me -(C=O)'Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0094 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0095 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0096 -CH ₂ -C=CH -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0097 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0098 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0099 -CH ₂ -C=CH -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0100 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0101 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0102 -CH ₂ -C=CH -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0103 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0104 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0105 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0106 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0107 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0108 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0109 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0110 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0111 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0112 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0113 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0114 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0115 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0116 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0117 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0118 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0119 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0120 -CH ₂ -C=CH -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0121 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0122 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl-

- 9 040613

1.0123 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0124 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0125 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0126 -CII, -C=CII -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0127 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0128 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0129 -CII, -C=CII -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0130 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0131 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0132 -CII, -C=CII -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0133 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0134 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0135 -si ₂ -s=si -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0136 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-pyridyl- 1.0137 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0138 -si ₂ -s=si -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0139 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0140 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0141 -si ₂ -s=si -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0142 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0143 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0144 -si ₂ -s=si -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0145 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0146 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0147 -CH ₂ -OCH -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0148 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0149 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0150 -si ₂ -s=si -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0151 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0152 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0153 -si ₂ -s=si -Me -(C=O)'Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0154 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4 something lil- 1.0155 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - -Ph 1.0156 -Me -Me -H 6-F -H (E) -CH=CH- -Ph 1.0157 -Me -Me -H 6-F -H trans- r H c H ₂ c-CH 1 -Ph

- 10 040613

1.0158 -Me -Me -H 6-F -H cis-TH c H ₂ C-CH 1 -Ph 1.0159 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - -Ph 1.0160 -Me -Me -H 6-C1 -H trans-TH c H ₂ C-CH 1 -Ph 1.0161 -Me -Me -H 6-C1 -H cis- r H c H,C-CH 1 -Ph 1.0162 -CH ₂ -C=CH -Me -H 6-F -H -CH ₂ -CH ₂ - -Ph 1.0163 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - -Ph 1.0164 -sn ₂ -osn -Me -H 6-C1 -H -CH ₂ -CH ₂ - -Ph 1.0165 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - -Ph 1.0166 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0167 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0168 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0169 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0170 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0171 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0172 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0173 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0174 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0175 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0176 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0177 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0178 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0179 -sn ₂ -s-sn -Me -H 6-F -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0180 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0181 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0182 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0183 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0184 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0185 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0186 cycloprop -Me -H 6-F -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl-

- 11 040613

IL 1.0187 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0188 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0189 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0190 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0191 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0192 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0193 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0194 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0195 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0196 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0197 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0198 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0199 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0200 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0201 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0202 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0203 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0204 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0205 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0206 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0207 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0208 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0209 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0210 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0211 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0212 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0213 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0214 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0215 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0216 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0217 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0218 -CH ₂ -C~CH -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0219 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0220 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0221 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0222 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0223 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0224 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl-

- 12 040613

1.0225 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0226 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-tolyl- 1.0227 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 4-tolyl- 1.0228 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-tolyl- 1.0229 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-tolyl- 1.0230 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-tolyl- 1.0231 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-tolyl- 1.0232 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - -Ph 1.0233 -Me -Me -(C=O)‘Pr 6-F -H (E) -CH=CH- -Ph 1.0234 -Me -Me -(C=O)*Pr 6-F -H trans- r H c H ₂ C-CH 1 -Ph 1.0235 -Me -Me -(C=O)*Pr 6-F -H cis-TH c H ₂ C-CH 1 -Ph 1.0236 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - -Ph 1.0237 -Me -Me -(C=O)‘Pr 6-C1 -H trans-TH c H ₂ C-CH 1 -Ph 1.0238 -Me -Me -(C=O)*Pr 6-C1 -H cis-THC / \ H ₂ C-CH 1 -Ph 1.0239 -CH ₂ -C=CH -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - -Ph 1.0240 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - -Ph 1.0241 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - -Ph 1.0242 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - -Ph 1.0243 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0244 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0245 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0246 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0247 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0248 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-chlorophenyl- 1.0249 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0250 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0251 - -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl-

- 13 040613

cyclopropyl 1.0252 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0253 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0254 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethylphenyl- 1.0255 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0256 -CII, -C=CII -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0257 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0258 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0259 -SP,-S=SP -Me -(C=O) ^lPr 6-C1 -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0260 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-cyanophenyl- 1.0261 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0262 -si ₂ -s=si -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0263 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0264 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0265 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0266 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-chloro-3 -pyridyl- 1.0267 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0268 -CII, -C=CII -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0269 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0270 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0271 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0272 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-chlorothiazol-5-yl- 1.0273 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0274 -si ₂ -s=si -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0275 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0276 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0277 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0278 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-trifluoromethyl-3 -pyridyl- 1.0279 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0280 -CII, -C=CII -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0281 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0282 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0283 -sn ₂ -osn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0284 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-fluorophenyl- 1.0285 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0286 -SI, -C=SI -Me -(C=O)Pr 6-F -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0287 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0288 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-pyridyl-

- 14 040613

1.0289 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0290 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-pyridyl- 1.0291 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0292 -CH,-C=CH -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0293 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0294 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0295 -CH,-C=CH -Me -(C=O)*Pr 6-C1 -II -CII ₂ -CII ₂ - 3,4-difluorophenyl- 1.0296 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3,4-difluorophenyl- 1.0297 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0298 -CH ₂ -C=CH -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0299 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0300 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0301 -CH,-C=CH -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0302 cycloprop silt -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethylphenyl- 1.0303 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4 something lil- 1.0304 -CH,-C=CH -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4 something lil- 1.0305 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4 something lil- 1.0306 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4 something lil- 1.0307 -CH,-C=CH -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4 something lil- 1.0308 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4 something lil- 1.0309 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0310 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0311 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0312 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0313 -sn, -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0314 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0315 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0316 -sn, -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0317 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0318 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0319 -CH,-C=CH -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0320 cycloprop silt -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0321 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0322 -CH,-C=CH -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0323 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0324 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0325 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0326 cycloprop -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl-

- 15 040613

IL 1.0327 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0328 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0329 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0330 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0331 -si ₂ -s=si -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0332 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0333 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0334 -CH,-C=CH -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0335 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0336 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0337 -CII, -C=CII -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0338 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0339 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0340 -CII, -C=CII -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0341 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0342 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0343 -CII, -C=CII -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0344 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0345 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0346 -CII, -C=CII -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0347 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0348 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0349 -CH ₂ -C=CH -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0350 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0351 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0352 -CII, -C=CII -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0353 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0354 -Ms -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 1 -mstil-3 (trifluoromethyl)pyrazol-4yl- 1.0355 -si, -s=si -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0356 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0357 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0358 -si, -s=si -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0359 cycloprop -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl-

- 16 040613

IL 1.0360 -Me -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0361 -sn ₂ -s=sn -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0362 cyclopropyl -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0363 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0364 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0365 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0366 -Me -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0367 -sn ₂ -s=sn -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0368 cyclopropyl -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0369 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0370 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0371 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0372 -Me -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0373 -sn ₂ -osn -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0374 cyclopropyl -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0375 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0376 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0377 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0378 -Me -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0379 -sn ₂ -s=sn -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0380 cyclopropyl -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0381 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0382 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0383 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0384 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0385 -sn ₂ -s=sn -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0386 cyclopropyl -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0387 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0388 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0389 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0390 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0391 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0392 cyclopropyl -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0393 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0394 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0395 cyclopropyl -Me -(C=O) ^lPr 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0396 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0397 -sn ₂ -s=sn -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl-

- 17 040613

1.0398 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0399 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0400 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0401 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0402 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0403 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0404 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0405 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0406 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0407 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0408 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0409 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0410 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0411 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0412 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0413 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0414 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0415 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0416 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0417 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0418 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0419 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0420 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0421 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0422 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0423 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0424 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0425 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0426 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0427 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0428 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0429 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0430 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl-

- 18 040613

1.0431 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0432 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0433 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0434 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - thiazol-2-yl- 1.0435 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0436 -CII, -C=CII -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0437 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CII ₂ -CII ₂ - pyrimidin-5 -yl- 1.0438 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0439 -CII, -C=CII -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0440 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0441 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0442 -CII, -C=CII -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0443 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0444 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0445 -CII, -C=CII -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0446 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0447 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0448 -CII, -C=CII -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0449 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0450 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0451 -si ₂ -s=si -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0452 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - thiazol-5-yl- 1.0453 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0454 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0455 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0456 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0457 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0458 cycloprop silt -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0459 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0460 -CII, -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0461 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0462 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0463 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0464 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0465 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0466 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0467 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl-

- 19 040613

1.0468 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0469 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0470 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0471 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0472 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0473 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0474 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0475 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0476 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-fluorofsnil- 1.0477 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0478 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0479 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0480 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0481 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0482 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0483 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0484 -CH,-C=CH -Me -H 6-F -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0485 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0486 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0487 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0488 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0489 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0490 -CH,-C=CH -Me -H 6-F -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0491 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0492 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0493 -CH,-C=CH -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0494 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0495 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0496 -CH,-C=CH -Me -H 6-F -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0497 cycloprop silt -Me -H 6-F -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0498 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0499 -CH,-C=CH -Me -H 6-C1 -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0500 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl-

- 20 040613

1.0501 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0502 -sn ₂ -osn -Me -H 6-F -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0503 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0504 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0505 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0506 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0507 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0508 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0509 cycloprop silt -Me -H 6-F -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0510 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0511 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0512 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0513 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0514 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0515 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0516 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0517 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0518 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0519 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0520 -sn ₂ -osn -Me -H 6-F -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0521 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0522 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0523 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0524 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0525 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0526 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0527 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0528 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0529 -sp ₂ -s = si -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0530 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-(trifluoromethoxy)-phenyl- 1.0531 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0532 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0533 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0534 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0535 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0536 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-3 -pyridyl- 1.0537 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0538 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0539 - -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl-

- 21 040613

cyclopropyl 1.0540 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0541 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0542 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-chloro-4-pyridyl- 1.0543 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0544 -CII, -C=CII -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0545 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0546 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0547 -si ₂ -s=si -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0548 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-fluorophenyl- 1.0549 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0550 -si ₂ -s=si -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0551 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0552 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0553 -CII, -C=CII -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0554 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-chloro-4-pyridyl- 1.0555 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0556 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0557 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0558 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0559 -CII, -C=CII -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0560 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-hydroxyphenyl- 1.0561 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0562 -CII, -C=CII -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0563 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0564 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0565 -CII, -C=CII -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0566 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 4-cyclopropylphenyl- 1.0567 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0568 -CII, -C=CII -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0569 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0570 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0571 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.0572 - -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 1-methyl-3-

- 22 040613

cyclopropyl (trifluoromethyl)pyrazol-4yl- 1.0573 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0574 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0575 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0576 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0577 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0578 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - thiazol-2-yl- 1.0579 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0580 -si, -s=sp -Me -(C=O) ^lPr 6-F -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0581 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0582 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0583 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0584 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - pyrimidin-5 -yl- 1.0585 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0586 -sn ₂ -osn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0587 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0588 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0589 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0590 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-(tert-butoxy)-phenyl- 1.0591 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0592 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0593 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0594 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0595 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0596 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - thiazol-5-yl- 1.0597 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0598 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0599 -CH ₂ -OCH -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0600 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0601 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0602 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0603 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0604 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0605 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0606 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0607 -CH ₂ -C \u003d SI -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0608 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0609 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl-

- 23 040613

1.0610 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0611 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0612 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0613 -CII, -C=CII -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0614 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0615 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2 something lil- 1.0616 -CH,-C=CH -Me -H 6-F 3-C1 -CII ₂ -CII ₂ - 2 something lil- 1.0617 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2 something lil- 1.0618 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2 something lil- 1.0619 -CII ₂ -C=CII -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2 something lil- 1.0620 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2 something lil- 1.0621 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0622 -CII, -C=CII -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0623 cycloprop silt -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0624 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0625 -CII, -C=CII -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0626 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0627 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0628 -CII, -C=CII -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0629 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0630 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0631 -CII, -C=CII -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0632 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0633 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0634 -CII, -C=CII -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0635 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0636 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0637 -CII, -C=CII -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0638 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0639 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0640 -CII, -C=CII -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0641 cycloprop silt -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0642 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0643 -CII, -C=CII -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0644 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0645 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0646 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0647 cycloprop -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl-

- 24 040613

IL 1.0648 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0649 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0650 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0651 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0652 -si ₂ -s=si -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0653 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0654 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0655 -si ₂ -s=si -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0656 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0657 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0658 -si ₂ -s=si -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0659 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0660 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0661 -si ₂ -s=si -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0662 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0663 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0664 -si ₂ -s=si -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0665 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0666 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0667 -si ₂ -s=si -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0668 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0669 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0670 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0671 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0672 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0673 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0674 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0675 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0676 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0677 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0678 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0679 -sn ₂ -osn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0680 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0681 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0682 -si ₂ -s=si -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0683 cyclopropyl -Me -(C=O) ^lPr 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0684 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0685 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl-

- 25 040613

1.0686 cyclopropyl -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0687 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-tolyl- 1.0688 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-tolyl- 1.0689 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-tolyl- 1.0690 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-tolyl- 1.0691 -CH,-C=CH -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-tolyl- 1.0692 cyclopropyl -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-tolyl- 1.0693 -Me -Me -(C=O)'Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0694 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0695 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0696 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0697 -sn ₂ -s=sn -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0698 cyclopropyl -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 3-tolyl- 1.0699 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0700 -CH,-C=CH -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0701 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0702 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0703 -CH,-C=CH -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0704 cyclopropyl -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0705 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0706 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0707 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0708 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0709 -sn ₂ -s=sn -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0710 cyclopropyl -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0711 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0712 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0713 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0714 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0715 -sn ₂ -s=sn -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0716 cyclopropyl -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0717 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0718 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0719 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0720 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0721 -sn ₂ -s=sn -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0722 cyclopropyl -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl-

- 26 040613

1.0723 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0724 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0725 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0726 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0727 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0728 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-pyridyl- 1.0729 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0730 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0731 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0732 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0733 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0734 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0735 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0736 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0737 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0738 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0739 -sn ₂ -osn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0740 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-aminophenyl- 1.0741 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0742 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0743 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0744 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0745 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0746 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0747 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0748 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0749 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0750 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0751 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0752 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0753 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0754 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0755 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0756 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0757 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0758 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0759 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2 something lil- 1.0760 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 2 something lil- 1.0761 - -Me -H 6-F -H -CH ₂ -CH ₂ - 2 something lil-

- 27 040613

cyclopropyl 1.0762 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-tolyl- 1.0763 -CH ₂ -C=CH -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-tolyl- 1.0764 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-tolyl- 1.0765 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3 -tolyl- 1.0766 -CII, -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 3 -tolyl- 1.0767 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3 -tolyl- 1.0768 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3 -tolyl- 1.0769 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3 -tolyl- 1.0770 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3 -tolyl- 1.0771 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0772 -CII ₂ -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0773 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0774 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0775 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0776 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0777 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0778 -CII ₂ -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0779 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0780 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0781 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0782 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0783 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0784 -CII ₂ -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0785 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0786 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0787 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0788 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0789 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0790 -CII ₂ -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0791 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0792 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0793 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0794 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0795 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0796 -CII ₂ -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0797 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0798 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-pyridyl-

- 28 040613

1.0799 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0800 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0801 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0802 -CH ₂ -C=CH -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0803 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0804 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0805 -CH ₂ -C=CH -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0806 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0807 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0808 -CH ₂ -C=CH -Me -H 6-F -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0809 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0810 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0811 -CH ₂ -C=CH -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0812 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0813 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0814 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0815 -sn ₂ -osn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0816 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0817 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0818 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-cyanophenyl- 1.0819 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0820 -CH ₂ -C=CH -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0821 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0822 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0823 -CH ₂ -C=CH -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0824 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-cyanophenyl- 1.0825 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0826 -CH ₂ -C=CH -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0827 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0828 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0829 -CH ₂ -C=CH -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0830 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethylphenyl- 1.0831 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2 something lil- 1.0832 -CH ₂ -C=CH -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2 something lil- 1.0833 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2 something lil- 1.0834 -Me -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2 something lil- 1.0835 -CH ₂ -C=CH -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2 something lil- 1.0836 cycloprop -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2 something lil-

- 29 040613

1.0837 IL -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-tolyl- 1.0838 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-tolyl- 1.0839 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-tolyl- 1.0840 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-tolyl- 1.0841 -si ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-tolyl- 1.0842 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-tolyl- 1.0843 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0844 -sn ₂ -osn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0845 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0846 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0847 -si ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0848 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-methyl-4-pyridyl- 1.0849 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0850 -si ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0851 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0852 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0853 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0854 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-trifluoromethyl-4-pyridyl- 1.0855 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0856 -CII, -C=CII -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0857 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0858 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0859 -CII, -C=CII -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0860 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-amino -4-pyridyl- 1.0861 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0862 -CII, -C=CII -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0863 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0864 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0865 -CII, -C=CII -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0866 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-fluoro-4-pyridyl- 1.0867 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0868 -si ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0869 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0870 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0871 -si ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0872 cyclopropyl -Me -(C=O) ^lPr 6-C1 -H -CH ₂ -CH ₂ - 4-pyridyl- 1.0873 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0874 -si ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl-

- 30 040613

1.0875 cycloprop silt -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0876 -Me -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0877 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0878 cyclopropyl -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 4-(methylamino)-phenyl- 1.0879 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0880 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0881 cyclopropyl -Me -(C=O)‘Pr 6-F -II -SP ₂ -SP ₂ - 4-aminophenyl- 1.0882 -Me -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0883 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0884 cyclopropyl -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 4-aminophenyl- 1.0885 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0886 -Me -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0887 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0888 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0889 -sn ₂ -s=sn -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0890 cyclopropyl -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0891 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0892 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0893 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0894 -Me -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0895 -sn ₂ -s=sn -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0896 cyclopropyl -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0897 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0898 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0899 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0900 -Me -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0901 -sn ₂ -s=sn -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0902 cyclopropyl -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0903 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0904 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0905 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0906 -Me -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0907 -sn ₂ -s=sn -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0908 cyclopropyl -Me -H 6-Cl 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0909 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.0910 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.0911 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl-

- 31 040613

1.0912 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-methylgriazo l-4 -yl- 1.0913 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.0914 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.0915 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.0916 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.0917 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.0918 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.0919 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.0920 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.0921 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0922 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0923 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0924 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0925 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0926 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0927 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.0928 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.0929 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.0930 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.0931 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.0932 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.0933 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.0934 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.0935 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.0936 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.0937 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.0938 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.0939 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.0940 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.0941 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.0942 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.0943 -sn ₂ -osn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.0944 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.0945 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.0946 -sn, -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.0947 cycloprop -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl-

- 32 040613

IL 1.0948 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.0949 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.0950 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.0951 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.0952 -si ₂ -s=si -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.0953 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.0954 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.0955 -sn, -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.0956 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.0957 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0958 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0959 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0960 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0961 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0962 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.0963 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0964 -si ₂ -s=si -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0965 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0966 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0967 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0968 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.0969 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0970 -si ₂ -s=si -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0971 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - thiophen-3-yl- 1.0972 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0973 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0974 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - thiophene-3 -yl- 1.0975 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0976 -si ₂ -s=si -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0977 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0978 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0979 -CH ₂ -C~CH -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0980 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.0981 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.0982 -si ₂ -s=si -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.0983 cyclopropyl -Me -(C=O) ^lPr 6-F 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.0984 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.0985 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl-

- 33 040613

1.0986 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 2-methylgriazo l-4 -yl- 1.0987 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 5 -methyl-1,3,4-oxadiazol-2 yl- 1.0988 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 5 -methyl-1,3,4-oxadiazol-2 yl- 1.0989 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 5 -methyl-1,3,4-oxadiazol-2 yl- 1.0990 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 5 -methyl-1,3,4-oxadiazol-2 yl- 1.0991 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 5 -methyl-1,3,4-oxadiazol-2 yl- 1.0992 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 5 -methyl-1,3,4-oxadiazol-2 yl- 1.0993 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0994 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0995 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0996 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0997 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0998 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.0999 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1000 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1001 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1002 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1003 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1004 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1005 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1006 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1007 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1008 -Me -Me -(C=O)Tg 6-C1 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1009 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1010 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1011 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1012 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1013 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1014 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1015 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1016 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1017 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1018 -CH ₂ -OCH -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1019 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1020 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl-

- 34 040613

1.1021 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1022 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1023 -Me -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1024 -CH,-C=CH -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1025 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1026 -Me -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1027 -SP ₂ -C=SP -Me -(C=O)‘Pr 6-C1 3-C1 -CII ₂ -CII ₂ - 3-trifluoromethyl-3-pyridyl- 1.1028 cyclopropyl -Me -(C=O)‘Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1029 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1030 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1031 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1032 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1033 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1034 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1035 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1036 -CII ₂ -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1037 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1038 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1039 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1040 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1041 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - thiophen-3-yl- 1.1042 -CII ₂ -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - thiophen-3-yl- 1.1043 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - thiophen-3-yl- 1.1044 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - thiophen-3-yl- 1.1045 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - thiophen-3-yl- 1.1046 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - thiophen-3-yl- 1.1047 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1048 -CII ₂ -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1049 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1050 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1051 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1052 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1053 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1054 -CII ₂ -C=CII -Me -H 6-F -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1055 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1056 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1057 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1058 cycloprop -Me -H 6-C1 -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl-

- 35 040613

IL 1.1059 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 5 -methyl-l,3,4-oxadiazol-2yl- 1.1060 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.1061 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.1062 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.1063 -CH,-C=CH -Me -H 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.1064 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.1065 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1066 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1067 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1068 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1069 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1070 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1071 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1072 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1073 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1074 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1075 -sn ₂ -osn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1076 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1077 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1078 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1079 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1080 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1081 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1082 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1083 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1084 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1085 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1086 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1087 -si ₂ -s=si -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1088 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1089 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1090 -si ₂ -s=si -Me -H 6-F -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1091 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1092 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1093 -CII ₂ -C=CII -Me -H 6-C1 -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1094 - -Me -H 6-C1 -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl-

- 36 040613

cyclopropyl 1.1095 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1096 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1097 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1098 -Me -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1099 -sn ₂ -s=sn -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1100 cyclopropyl -Me -H 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1101 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1102 -Me -Me -(C=O) ^lPr 6-C1 -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1103 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1104 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1105 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1106 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl- 1.1107 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1108 -sn ₂ -osn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1109 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1110 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1111 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1112 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-4-aminophenyl- 1.1113 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - thiophene-3 -yl- 1.1114 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - thiophene-3 -yl- 1.1115 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - thiophene-3 -yl- 1.1116 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - thiophene-3 -yl- 1.1117 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - thiophene-3 -yl- 1.1118 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - thiophene-3 -yl- 1.1119 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1120 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1121 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1122 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1123 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1124 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 1-methylpyrazol-4-yl- 1.1125 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1126 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1127 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1128 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1129 -SI ₂ -C=SI -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1130 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 2-methyltriazol-4 -yl- 1.1131 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazole-2-

- 37 040613

IL- 1.1132 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 5 -methyl-l,3,4-oxadiazol-2yl- 1.1133 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.1134 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.1135 -CII, -C=CII -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.1136 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-1,3,4-oxadiazol-2yl- 1.1137 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1138 -CII, -C=CII -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1139 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1140 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1141 -CII, -C=CII -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1142 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-3-pyridyl- 1.1143 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1144 -CII, -C=CII -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1145 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1146 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1147 -CII, -C=CII -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1148 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 5-methyl-2-pyridyl- 1.1149 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1150 -si ₂ -s=si -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1151 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1152 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1153 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1154 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 6 -methyl-2 -pyridyl- 1.1155 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1156 -si ₂ -s=si -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1157 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1158 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1159 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1160 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-methyl-2-pyridyl- 1.1161 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1162 -si ₂ -s=si -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1163 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1164 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1165 -si ₂ -s=si -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl- 1.1166 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 6-chloro-3 -pyridyl-

- 38 040613

1.1167 -Me -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1168 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1169 cyclopropyl -Me -(C=O)*Pr 6-F -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1170 -Me -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1171 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1172 cyclopropyl -Me -(C=O)*Pr 6-C1 -H -CH ₂ -CH ₂ - 3-trifluoromethyl-3-pyridyl- 1.1173 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1174 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1175 -sn, -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1176 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1177 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1178 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1179 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1180 -sn ₂ -s=sn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1181 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1182 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1183 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1184 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1185 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1186 -sn ₂ -osn -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1187 cyclopropyl -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1188 -Me -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1189 -sn ₂ -s=sn -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1190 cyclopropyl -Me -H 6-C1 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1191 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1192 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1193 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1194 cyclopropyl -Me -(C=O)‘Pr 6-F 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1195 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1196 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1197 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1198 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1199 cyclopropyl -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1200 -Me -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1201 -sn ₂ -s=sn -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1202 cyclopropyl -Me -(C=O)*Pr 6-C1 3-C1 -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1203 -Me -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1204 -sn ₂ -s=sn -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1205 - -Me -(C=O)*Pr 6-F 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl-

- 39 040613

cyclopropyl 1.1206 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1207 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1208 cyclopropyl -Me -(C=O)‘Pr 6-Cl 3-C1 -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1209 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1210 -Me -Me -H 6-Cl -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1211 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1212 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1213 -sn ₂ -s=sn -Me -H 6-Cl -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1214 cyclopropyl -Me -H 6-Cl -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1215 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1216 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1217 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1218 -Me -Me -H 6-Cl -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1219 -sn ₂ -osn -Me -H 6-Cl -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1220 cyclopropyl -Me -H 6-Cl -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1221 -Me -Me -H 6-F -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1222 -sn ₂ -s=sn -Me -H 6-F -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1223 cyclopropyl -Me -H 6-F -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1224 -Me -Me -H 6-Cl -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1225 -sn ₂ -s=sn -Me -H 6-Cl -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1226 cyclopropyl -Me -H 6-Cl -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1227 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1228 -Me -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1229 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1230 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1231 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1232 cyclopropyl -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 3,5-difluorophenyl- 1.1233 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1234 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1235 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1236 -Me -Me -(C=O)*Pr 6-Cl -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1237 -sn ₂ -s=sn -Me -(C=O)*Pr 6-Cl -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1238 cyclopropyl -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 4-methyl-2-pyridyl- 1.1239 -Me -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1240 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1241 cyclopropyl -Me -(C=O)‘Pr 6-F -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1242 -Me -Me -(C=O)‘Pr 6-Cl -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl-

- 40 040613

1.1243 -sn ₂ -s=sn -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1244 cyclopropyl -Me -(C=O)‘Pr 6-C1 -H -CH ₂ -CH ₂ - 2-acetamidothiazol-5-yl- 1.1245 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-chlorophenyl- 1.1246 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-trifluoromethylphenyl- 1.1247 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-cyanophenyl- 1.1248 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-chloro-3 -pyridyl- 1.1249 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-chlorothiazol-5-yl- 1.1250 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-trifluoromethyl-3-pyridyl- 1.1251 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-fluorophenyl- 1.1252 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3-pyridyl- 1.1253 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3,4-difluorophenyl- 1.1254 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-trifluoromethylphenyl- 1.1255 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4 something lil- 1.1256 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-(trifluoromethoxy)-phenyl- 1.1257 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-chloro-3 -pyridyl- 1.1258 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-chloro-4-pyridyl- 1.1259 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3-chloro-4-fluorophenyl- 1.1260 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3-chloro-4-pyridyl- 1.1261 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-hydroxyphenyl- 1.1262 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-cyclopropylphenyl- 1.1263 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.1264 -Me -Me -H 6-F 3-C1 (E) -CH=CH- thiazol-2-yl- 1.1265 -Me -Me -H 6-F 3-C1 (E) -CH=CH- pyrimidin-5 -yl- 1.1266 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-(tert-butoxy)-phenyl- 1.1267 -Me -Me -H 6-F 3-C1 (E) -CH=CH- thiazol-5-yl- 1.1268 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-cyanophenyl- 1.1269 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3-cyanophenyl- 1.1270 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3-trifluoromethylphenyl- 1.1271 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2 something lil- 1.1272 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3-tolyl- 1.1273 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-methyl-4-pyridyl- 1.1274 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-trifluoromethyl-4-pyridyl- 1.1275 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-amino -4-pyridyl- 1.1276 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-fluoro-4-pyridyl- 1.1277 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-pyridyl- 1.1278 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-(methylamino)-phenyl- 1.1279 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-aminophenyl- 1.1280 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-(dimethylamino)-phenyl- 1.1281 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3-methyl-4-aminophenyl- 1.1282 -Me -Me -H 6-F 3-C1 (E) -CH=CH- thiophene-3 -yl- 1.1283 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 1-methylpyrazol-4-yl- 1.1284 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-methyltriazol-4 -yl- 1.1285 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 5-methyl-1,3,4-oxadiazol-2yl- 1.1286 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 5-methyl-3-pyridyl- 1.1287 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 5-methyl-2-pyridyl- 1.1288 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 6 -methyl-2 -pyridyl- 1.1289 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3-methyl-2-pyridyl- 1.1290 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 6-chloro-3 -pyridyl- 1.1291 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3-trifluoromethyl-3-pyridyl- 1.1292 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 3,5-difluorophenyl- 1.1293 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 4-methyl-2-pyridyl- 1.1294 -Me -Me -H 6-F 3-C1 (E) -CH=CH- 2-acetamidothiazol-5-yl- 1.1295 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- -Ph 1.1296 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-chlorophenyl- 1.1297 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-trifluoromethylphenyl- 1.1298 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-cyanophenyl- 1.1299 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-chloro-3 -pyridyl-

- 41 040613

1.1300 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-chlorothiazol-5-yl- 1.1301 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-trifluoromethyl-3 -pyridyl- 1.1302 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-fluorophenyl- 1.1303 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3-pyridyl- 1.1304 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3,4-difluorophenyl- 1.1305 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-trifluoromethylphenyl- 1.1306 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4 something lil- 1.1307 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-(trifluoromethoxy)-phenyl- 1.1308 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-chloro-3 -pyridyl- 1.1309 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-chloro-4-pyridyl- 1.1310 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3-chloro-4-fluorophenyl- 1.1311 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3-chloro-4-pyridyl- 1.1312 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-hydroxyphenyl- 1.1313 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-cyclopropylphenyl- 1.1314 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.1315 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- thiazol-2-yl- 1.1316 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- pyrimidin-5 -yl- 1.1317 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-(tert-butoxy)-phenyl- 1.1318 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- thiazol-5-yl- 1.1319 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-cyanophenyl- 1.1320 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3-cyanophenyl- 1.1321 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3-trifluoromethylphenyl- 1.1322 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2 something lil- 1.1323 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3-tolyl- 1.1324 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-methyl-4-pyridyl- 1.1325 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-trifluoromethyl-4-pyridyl- 1.1326 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-amino -4-pyridyl- 1.1327 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-fluoro-4-pyridyl- 1.1328 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-pyridyl- 1.1329 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-(methylamino)-phenyl- 1.1330 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-aminophenyl- 1.1331 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-(dimethylamino)-phenyl- 1.1332 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3-methyl-4-aminophenyl- 1.1333 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- thiophene-3 -yl- 1.1334 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 1-methylpyrazol-4-yl- 1.1335 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-methyltriazol-4 -yl- 1.1336 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 5-methyl-1,3,4-oxadiazol-2yl- 1.1337 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 5-methyl-3-pyridyl- 1.1338 -Me -Me -II 6-C1 3-C1 (E) -CH=CH- 5 -avenged-2 -pyridyl- 1.1339 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 6 -methyl-2 -pyridyl- 1.1340 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3-methyl-2-pyridyl- 1.1341 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 6-chloro-3 -pyridyl- 1.1342 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3-trifluoromethyl-3-pyridyl- 1.1343 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 3,5-difluorophenyl- 1.1344 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 4-methyl-2-pyridyl- 1.1345 -Me -Me -H 6-C1 3-C1 (E) -CH=CH- 2-acetamidothiazol-5-yl- 1.1346 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-chlorophenyl- 1.1347 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-trifluoromethylphenyl- 1.1348 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-cyanophenyl- 1.1349 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-chloro-3 -pyridyl- 1.1350 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-chlorothiazol-5-yl- 1.1351 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-trifluoromethyl-3 -pyridyl- 1.1352 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-fluorophenyl- 1.1353 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3-pyridyl- 1.1354 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3,4-difluorophenyl- 1.1355 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-trifluoromethylphenyl- 1.1356 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4 something lil- 1.1357 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-(trifluoromethoxy)-phenyl- 1.1358 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-chloro-3 -pyridyl-

- 42 040613

1.1359 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-chloro-4-pyridyl- 1.1360 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3-chloro-4-fluorophenyl- 1.1361 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3-chloro-4-pyridyl- 1.1362 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-hydroxyphenyl- 1.1363 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-cyclopropylphenyl- 1.1364 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.1365 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- thiazol-2-yl- 1.1366 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- pyrimidin-5 -yl- 1.1367 -Me -Me -(C=O)‘Pr 6-F 3-C1 (E) -CH=CH- 4-(tert-butoxy)-phenyl- 1.1368 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- thiazol-5-yl- 1.1369 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-cyanophenyl- 1.1370 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3-cyanophenyl- 1.1371 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3-trifluoromethylphenyl- 1.1372 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-tolyl- 1.1373 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3-tolyl- 1.1374 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-methyl-4-pyridyl- 1.1375 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-trifluoromethyl-4-pyridyl- 1.1376 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-amino -4-pyridyl- 1.1377 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-fluoro-4-pyridyl- 1.1378 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-pyridyl- 1.1379 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-(methylamino)-phenyl- 1.1380 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-aminophenyl- 1.1381 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-(dimethylamino)-phenyl- 1.1382 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3-methyl-4-aminophenyl- 1.1383 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- thiophene-3 -yl- 1.1384 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 1-methylpyrazol-4-yl- 1.1385 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-methyltriazol-4 -yl- 1.1386 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 5-methyl-1,3,4-oxadiazol-2yl- 1.1387 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 5-methyl-3-pyridyl- 1.1388 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 5-methyl-2-pyridyl- 1.1389 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 6 -methyl-2 -pyridyl- 1.1390 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3-methyl-2-pyridyl- 1.1391 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 6-chloro-3 -pyridyl- 1.1392 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3-trifluoromethyl-3-pyridyl- 1.1393 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 3,5-difluorophenyl- 1.1394 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 4-methyl-2-pyridyl- 1.1395 -Me -Me -(C=O)*Pr 6-F 3-C1 (E) -CH=CH- 2-acetamidothiazol-5-yl- 1.1396 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- -Ph 1.1397 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-chlorophenyl- 1.1398 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-trifluoromethylphenyl- 1.1399 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-cyanophenyl- 1.1400 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-chloro-3 -pyridyl- 1.1401 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-chlorothiazol-5-yl- 1.1402 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-trifluoromethyl-3-pyridyl- 1.1403 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-fluorophenyl- 1.1404 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3-pyridyl- 1.1405 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3,4-difluorophenyl- 1.1406 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-trifluoromethylphenyl- 1.1407 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4 something lil- 1.1408 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-(trifluoromethoxy)-phenyl- 1.1409 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-chloro-3 -pyridyl- 1.1410 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-chloro-4-pyridyl- 1.1411 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3-chloro-4-fluorophenyl- 1.1412 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3-chloro-4-pyridyl- 1.1413 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-hydroxyphenyl- 1.1414 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-cyclopropylphenyl- 1.1415 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 1 -methyl-3 (trifluoromethyl) pyrazol-4yl-

- 43 040613

1.1416 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- thiazol-2-yl- 1.1417 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- pyrimidin-5 -yl- 1.1418 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-(tert-butoxy)-phenyl- 1.1419 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- thiazol-5-yl- 1.1420 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-cyanophenyl- 1.1421 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3-cyanophenyl- 1.1422 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3-trifluoromethylphenyl- 1.1423 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2 something lil- 1.1424 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3-tolyl- 1.1425 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-methyl-4-pyridyl- 1.1426 -Me -Me -(C=O)‘Pr 6-C1 3-C1 (E) -CH=CH- 2-trifluoromethyl-4-pyridyl- 1.1427 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-amino -4-pyridyl- 1.1428 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-fluoro-4-pyridyl- 1.1429 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-pyridyl- 1.1430 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-(methylamino)-phenyl- 1.1431 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-aminophenyl- 1.1432 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-(dimethylamino)-phenyl- 1.1433 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3-methyl-4-aminophenyl- 1.1434 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- thiophene-3 -yl- 1.1435 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 1-methylpyrazol-4-yl- 1.1436 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-methyltriazol-4 -yl- 1.1437 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 5-methyl-1,3,4-oxadiazol-2yl- 1.1438 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 5-methyl-3-pyridyl- 1.1439 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 5-methyl-2-pyridyl- 1.1440 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 6 -methyl-2 -pyridyl- 1.1441 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3-methyl-2-pyridyl- 1.1442 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 6-chloro-3 -pyridyl- 1.1443 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3-trifluoromethyl-3-pyridyl- 1.1444 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 3,5-difluorophenyl- 1.1445 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 4-methyl-2-pyridyl- 1.1446 -Me -Me -(C=O)*Pr 6-C1 3-C1 (E) -CH=CH- 2-acetamidothiazol-5-yl- 1.1447 -Me -Me -H 6-F 3-C1 -c=c- -Ph 1.1448 -Me -Me -H 6-F 3-C1 -c=c- 4-chlorophenyl- 1.1449 -Me -Me -H 6-F 3-C1 -c=c- 4-trifluoromethylphenyl- 1.1450 -Me -Me -H 6-F 3-C1 -c=c- 4-cyanophenyl- 1.1451 -Me -Me -H 6-F 3-C1 -oc- 4-chloro-3 -pyridyl- 1.1452 -Me -Me -H 6-F 3-C1 -c=c- 2-chlorothiazol-5-yl- 1.1453 -Me -Me -H 6-F 3-C1 -c=c- 4-trifluoromethyl-3 -pyridyl- 1.1454 -Me -Me -H 6-F 3-C1 -c=c- 4-fluorophenyl- 1.1455 -Me -Me -H 6-F 3-C1 -c=c- 3-pyridyl- 1.1456 -Me -Me -H 6-F 3-C1 -c=c- 3,4-difluorophenyl- 1.1457 -Me -Me -H 6-F 3-C1 -c=c- 2-trifluoromethylphenyl- 1.1458 -Me -Me -H 6-F 3-C1 -c=c- 4 something lil- 1.1459 -Me -Me -H 6-F 3-C1 -c=c- 4-(trifluoromethoxy)-phenyl- 1.1460 -Me -Me -H 6-F 3-C1 -c=c- 2-chloro-3 -pyridyl- 1.1461 -Me -Me -H 6-F 3-C1 -c=c- 2-chloro-4-pyridyl- 1.1462 -Me -Me -H 6-F 3-C1 -c=c- 3-chloro-4-fluorophenyl- 1.1463 -Me -Me -H 6-F 3-C1 -c=c- 3-chloro-4-pyridyl- 1.1464 -Me -Me -H 6-F 3-C1 -c=c- 4-hydroxyphenyl- 1.1465 -Me -Me -H 6-F 3-C1 -c=c- 4-cyclopropylphenyl- 1.1466 -Me -Me -H 6-F 3-C1 -c=c- 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.1467 -Me -Me -H 6-F 3-C1 -c=c- thiazol-2-yl- 1.1468 -Me -Me -H 6-F 3-C1 -c=c- pyrimidin-5 -yl- 1.1469 -Me -Me -H 6-F 3-C1 -c=c- 4-(tert-butoxy)-phenyl- 1.1470 -Me -Me -H 6-F 3-C1 -c=c- thiazol-5-yl- 1.1471 -Me -Me -H 6-F 3-C1 -c=c- 2-cyanophenyl- 1.1472 -Me -Me -H 6-F 3-C1 -c=c- 3-cyanophenyl- 1.1473 -Me -Me -H 6-F 3-C1 -c=c- 3-trifluoromethylphenyl- 1.1474 -Me -Me -H 6-F 3-C1 -c=c- 2 something lil-

- 44 040613

1.1475 -Me -Me -H 6-F 3-C1 -c=c- 3-tolyl- 1.1476 -Me -Me -H 6-F 3-C1 -c=c- 2-methyl-4-pyridyl- 1.1477 -Me -Me -H 6-F 3-C1 -c=c- 2-trifluoromethyl-4-pyridyl- 1.1478 -Me -Me -H 6-F 3-C1 -c=c- 2-amino -4-pyridyl- 1.1479 -Me -Me -H 6-F 3-C1 -c=c- 2-fluoro-4-pyridyl- 1.1480 -Me -Me -H 6-F 3-C1 -c=c- 4-pyridyl- 1.1481 -Me -Me -H 6-F 3-C1 -c=c- 4-(methylamino)-phenyl- 1.1482 -Me -Me -H 6-F 3-C1 -c=c- 4-aminophenyl- 1.1483 -Me -Me -H 6-F 3-C1 -c=c- 4-(dimethylamino)-phenyl- 1.1484 -Me -Me -H 6-F 3-C1 -c=c- 3-methyl-4-aminophenyl- 1.1485 -Me -Me -H 6-F 3-C1 -c=c- thiophen-3-yl- 1.1486 -Me -Me -H 6-F 3-C1 -c=c- 1-methylpyrazol-4-yl- 1.1487 -Me -Me -H 6-F 3-C1 -c=c- 2-methyltriazol-4 -yl- 1.1488 -Me -Me -H 6-F 3-C1 -c=c- 5-methyl-1,3,4-oxadiazol-2yl- 1.1489 -Me -Me -H 6-F 3-C1 -c=c- 5-methyl-3-pyridyl- 1.1490 -Me -Me -H 6-F 3-C1 -c=c- 5-methyl-2-pyridyl- 1.1491 -Me -Me -H 6-F 3-C1 -c=c- 6 -methyl-2 -pyridyl- 1.1492 -Me -Me -H 6-F 3-C1 -c=c- 3-methyl-2-pyridyl- 1.1493 -Me -Me -H 6-F 3-C1 -c=c- 6-chloro-3 -pyridyl- 1.1494 -Me -Me -H 6-F 3-C1 -C=C- 3-trifluoromethyl-3-pyridyl- 1.1495 -Me -Me -H 6-F 3-C1 -c=c- 3,5-difluorophenyl- 1.1496 -Me -Me -H 6-F 3-C1 -c=c- 4-methyl-2-pyridyl- 1.1497 -Me -Me -H 6-F 3-C1 -c=c- 2-acetamidothiazol-5-yl- 1.1498 -Me -Me -H 6-C1 3-C1 -c=c- -Ph 1.1499 -Me -Me -H 6-C1 3-C1 -c=c- 4-chlorophenyl- 1.1500 -Me -Me -H 6-C1 3-C1 -c=c- 4-trifluoromethylphenyl- 1.1501 -Me -Me -H 6-C1 3-C1 -c=c- 4-cyanophenyl- 1.1502 -Me -Me -H 6-C1 3-C1 -c=c- 4-chloro-3 -pyridyl- 1.1503 -Me -Me -H 6-C1 3-C1 -c=c- 2-chlorothiazol-5-yl- 1.1504 -Me -Me -H 6-C1 3-C1 -c=c- 4-trifluoromethyl-3 -pyridyl- 1.1505 -Me -Me -H 6-C1 3-C1 -c=c- 4-fluorophenyl- 1.1506 -Me -Me -H 6-C1 3-C1 -c=c- 3-pyridyl- 1.1507 -Me -Me -H 6-C1 3-C1 -c=c- 3,4-difluorophenyl- 1.1508 -Me -Me -H 6-C1 3-C1 -c=c- 2-trifluoromethylphenyl- 1.1509 -Me -Me -H 6-C1 3-C1 -c=c- 4 something lil- 1.1510 -Me -Me -H 6-C1 3-C1 -c=c- 4-(trifluoromethoxy)-phenyl- 1.1511 -Me -Me -H 6-C1 3-C1 -c=c- 2-chloro-3 -pyridyl- 1.1512 -Me -Me -H 6-C1 3-C1 -c=c- 2-chloro-4-pyridyl- 1.1513 -Me -Me -H 6-C1 3-C1 -c=c- 3-chloro-4-fluorophenyl- 1.1514 -Me -Me -H 6-C1 3-C1 -c=c- 3-chloro-4-pyridyl- 1.1515 -Me -Me -H 6-C1 3-C1 -c=c- 4-hydroxyphenyl- 1.1516 -Me -Me -H 6-C1 3-C1 -c=c- 4-cyclopropylphenyl- 1.1517 -Me -Me -H 6-C1 3-C1 -c=c- 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.1518 -Me -Me -H 6-C1 3-C1 -os- thiazol-2-yl- 1.1519 -Me -Me -H 6-C1 3-C1 -c=c- pyrimidin-5 -yl- 1.1520 -Me -Me -H 6-C1 3-C1 -c=c- 4-(tert-butoxy)-phenyl- 1.1521 -Me -Me -H 6-C1 3-C1 -c=c- thiazol-5-yl- 1.1522 -Me -Me -H 6-C1 3-C1 -c=c- 2-cyanophenyl- 1.1523 -Me -Me -H 6-C1 3-C1 -c=c- 3-cyanophenyl- 1.1524 -Me -Me -H 6-C1 3-C1 -c=c- 3-trifluoromethylphenyl- 1.1525 -Me -Me -H 6-C1 3-C1 -c=c- 2 something lil- 1.1526 -Me -Me -H 6-C1 3-C1 -c=c- 3-tolyl- 1.1527 -Me -Me -H 6-C1 3-C1 -c=c- 2-methyl-4-pyridyl- 1.1528 -Me -Me -H 6-C1 3-C1 -c=c- 2-trifluoromethyl-4-pyridyl- 1.1529 -Me -Me -H 6-C1 3-C1 -c=c- 2-amino -4-pyridyl- 1.1530 -Me -Me -H 6-C1 3-C1 -c=c- 2-fluoro-4-pyridyl- 1.1531 -Me -Me -H 6-C1 3-C1 -c=c- 4-pyridyl- 1.1532 -Me -Me -H 6-C1 3-C1 -c=c- 4-(methylamino)-phenyl- 1.1533 -Me -Me -H 6-C1 3-C1 -c=c- 4-aminophenyl-

- 45 040613

1.1534 -Me -Me -H 6-C1 3-C1 -c=c- 4-(dimethylamino)-phenyl- 1.1535 -Me -Me -H 6-C1 3-C1 -c=c- 3-methyl-4-aminophenyl- 1.1536 -Me -Me -H 6-C1 3-C1 -c=c- thiophen-3-yl- 1.1537 -Me -Me -H 6-C1 3-C1 -c=c- 1-methylpyrazol-4-yl- 1.1538 -Me -Me -H 6-C1 3-C1 -c=c- 2-methyltriazol-4 -yl- 1.1539 -Me -Me -H 6-C1 3-C1 -c=c- 5-methyl-1,3,4-oxadiazol-2yl- 1.1540 -Me -Me -H 6-C1 3-C1 -c=c- 5-methyl-3-pyridyl- 1.1541 -Me -Me -H 6-C1 3-C1 -c=c- 5-methyl-2-pyridyl- 1.1542 -Me -Me -H 6-C1 3-C1 -c=c- 6 -methyl-2 -pyridyl- 1.1543 -Me -Me -H 6-C1 3-C1 -c=c- 3-methyl-2-pyridyl- 1.1544 -Me -Me -H 6-C1 3-C1 -c=c- 6-chloro-3 -pyridyl- 1.1545 -Me -Me -H 6-C1 3-C1 -c=c- 3-trifluoromethyl-3-pyridyl- 1.1546 -Me -Me -H 6-C1 3-C1 -c=c- 3,5-difluorophenyl- 1.1547 -Me -Me -H 6-C1 3-C1 -c=c- 4-methyl-2-pyridyl- 1.1548 -Me -Me -H 6-C1 3-C1 -c=c- 2-acetamidothiazol-5-yl- 1.1549 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- -Ph 1.1550 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-chlorophenyl- 1.1551 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-trifluoromethylphenyl- 1.1552 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-cyanophenyl- 1.1553 -Me -Me -(C=O)*Pr 6-F 3-C1 -C=C- 4-chloro-3 -pyridyl- 1.1554 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-chlorothiazol-5-yl- 1.1555 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-trifluoromethyl-3-pyridyl- 1.1556 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-fluorophenyl- 1.1557 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 3-pyridyl- 1.1558 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 3,4-difluorophenyl- 1.1559 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-trifluoromethylphenyl- 1.1560 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4 something lil- 1.1561 -Me -Me -(C=O)*Pr 6-F 3-C1 -c=c- 4-(trifluoromethoxy)-phenyl- 1.1562 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-chloro-3 -pyridyl- 1.1563 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-chloro-4-pyridyl- 1.1564 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 3-chloro-4-fluorophenyl- 1.1565 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 3-chloro-4-pyridyl- 1.1566 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-hydroxyphenyl- 1.1567 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-cyclopropylphenyl- 1.1568 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.1569 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- thiazol-2-yl- 1.1570 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- pyrimidin-5 -yl- 1.1571 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-(tert-butoxy)-phenyl- 1.1572 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- thiazol-5-yl- 1.1573 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-cyanophenyl- 1.1574 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 3-cyanophenyl- 1.1575 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 3-trifluoromethylphenyl- 1.1576 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2 something lil- 1.1577 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 3-tolyl- 1.1578 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-methyl-4-pyridyl- 1.1579 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-trifluoromethyl-4-pyridyl- 1.1580 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-amino -4-pyridyl- 1.1581 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-fluoro-4-pyridyl- 1.1582 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-pyridyl- 1.1583 -Me -Me -(C=O)‘Pr 6-F 3-C1 -oc- 4-(methylamino)-phenyl- 1.1584 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-aminophenyl- 1.1585 -Me -Me -(C=O)*Pr 6-F 3-C1 -c=c- 4-(dimethylamino)-phenyl- 1.1586 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 3-methyl-4-aminophenyl- 1.1587 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- thiophene-3 -yl- 1.1588 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 1-methylpyrazol-4-yl- 1.1589 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 2-methyltriazol-4 -yl- 1.1590 -Me -Me -(C=O)*Pr 6-F 3-C1 -c=c- 5-methyl-1D4-oxadiazol-2yl- 1.1591 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 5-methyl-3-pyridyl-

- 46 040613

1.1592 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 5-methyl-2-pyridyl- 1.1593 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 6 -methyl-2 -pyridyl- 1.1594 -Me -Me -(C=O)*Pr 6-F 3-C1 -c=c- 3-methyl-2-pyridyl- 1.1595 -Me -Me -(C=O)*Pr 6-F 3-C1 -c=c- 6-chloro-3 -pyridyl- 1.1596 -Me -Me -(C=O)*Pr 6-F 3-C1 -c=c- 3-trifluoromethyl-3-pyridyl- 1.1597 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 3,5-difluorophenyl- 1.1598 -Me -Me -(C=O)‘Pr 6-F 3-C1 -c=c- 4-methyl-2-pyridyl- 1.1599 -Me -Me -(C=O)*Pr 6-F 3-C1 -c=c- 2-acetamidothiazol-5-yl- 1.1600 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- -Ph 1.1601 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 4-chlorophenyl- 1.1602 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 4-trifluoromethylphenyl- 1.1603 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 4-cyanophenyl- 1.1604 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 4-chloro-3 -pyridyl- 1.1605 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 2-chlorothiazol-5-yl- 1.1606 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 4-trifluoromethyl-3 -pyridyl- 1.1607 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 4-fluorophenyl- 1.1608 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 3-pyridyl- 1.1609 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 3,4-difluorophenyl- 1.1610 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 2-trifluoromethylphenyl- 1.1611 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 4 something lil- 1.1612 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -C=C- 4-(trifluoromethoxy)-phenyl- 1.1613 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 2-chloro-3 -pyridyl- 1.1614 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 2-chloro-4-pyridyl- 1.1615 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 3-chloro-4-fluorophenyl- 1.1616 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 3-chloro-4-pyridyl- 1.1617 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 4-hydroxyphenyl- 1.1618 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 4-cyclopropylphenyl- 1.1619 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 1 -methyl-3 (trifluoromethyl) pyrazol-4yl- 1.1620 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- thiazol-2-yl- 1.1621 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- pyrimidin-5 -yl- 1.1622 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 4-(tert-butoxy)-phenyl- 1.1623 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- thiazol-5-yl- 1.1624 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 2-cyanophenyl- 1.1625 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 3-cyanophenyl- 1.1626 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 3-trifluoromethylphenyl- 1.1627 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 2-tolyl- 1.1628 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 3-tolyl- 1.1629 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 2-methyl-4-pyridyl- 1.1630 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 2-trifluoromethyl-4-pyridyl- 1.1631 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 2-amino -4-pyridyl- 1.1632 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 2-fluoro-4-pyridyl- 1.1633 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 4-pyridyl- 1.1634 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 4-(methylamino)-phenyl- 1.1635 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 4-aminophenyl- 1.1636 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 4-(dimethylamino)-phenyl- 1.1637 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 3-methyl-4-aminophenyl- 1.1638 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- thiophen-3-yl- 1.1639 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 1-methylpyrazol-4-yl- 1.1640 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 2-methyltriazol-4 -yl- 1.1641 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 5-methyl-1,3,4-oxadiazol-2yl- 1.1642 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 5-methyl-3-pyridyl- 1.1643 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 5-methyl-2-pyridyl- 1.1644 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 6 -methyl-2 -pyridyl- 1.1645 -Me -Me -(C=O)‘Pr 6-Cl 3-C1 -c=c- 3-methyl-2-pyridyl- 1.1646 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 6-chloro-3 -pyridyl- 1.1647 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 3-trifluoromethyl-3-pyridyl- 1.1648 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 3,5-difluorophenyl- 1.1649 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 4-methyl-2-pyridyl- 1.1650 -Me -Me -(C=O)*Pr 6-Cl 3-C1 -c=c- 2-acetamidothiazol-5-yl- 1.1651 -Me -Me -(C=O)Me 6-F 3-C1 -CH ₂ -CH ₂ - P-TO LIL 1.1652 -Me -Me -(C=O)O'Bu 6-F 3-C1 -CH ₂ -CH ₂ - p-to lil 1.1653 -Me -Me -(C=O)OMe 6-F 3-C1 -CH ₂ -CH ₂ - p-to lil 1.1654 -Me -Me -(C=O)tBu 6-F 3-C1 -CH ₂ -CH ₂ - p-to lil 1.1655 -Me -Me -(C=O)Ph 6-F 3-C1 -CH ₂ -CH ₂ - p-to lil 1.1656 -Me -Me -(C=O)4morpholino 6-F 3-C1 -CH ₂ -CH ₂ - p-to lil

The numbering system used to describe the X and Y positions is shown for clarity only.

- 47 040613

As indicated herein above, a compound of formula (I) according to the present invention may have any combination of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ ,

R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , W, D, Dp, G, X, Y, Z ¹ , Z ² , Z ³ , Z ⁴ , Z ⁵ and m as above. However, the following combinations constitute specific groups of embodiments contemplated by the present invention.

One preferred combination of substituents provides a compound of formula (I) wherein R ¹ is methyl, -CH2-C=CH, or cyclopropyl; R ² is methyl, G is H, -C(O)C1-C4 alkyl, -C(O)OC ₁ -C ₄ alkyl, -C(O)-4-morpholino, or -C(O) -phenyl; X represents hydrogen, halogen or C ₁ haloalkyl; Y is hydrogen or halogen; W represents -CH ₂ -CH ₂ -, (E)-CH-CH- or -C=C-; D is either Dp, where Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are each independently selected from the group consisting of hydrogen, cyano, amino, di-C1-C3-alkylamino, hydroxy, C1-C3- alkyl, C1-C4-alkoxy, C1-C3-haloalkyl, C1-C3-haloalkoxy and halogen, or D is a substituted or unsubstituted pyridyl, pyrazolyl, thiazolyl, pyrimidinyl, thienyl, triazolyl or oxadiazolyl ring, whereby if the ring is substituted , it is substituted with 1 or 2 R ⁸ ; and each R ⁸ is independently selected from the group consisting of halo, amino, -NHC(O)C1-C3 alkyl, C1- _C4 alkyl, and C1- _C4 haloalkyl.

An additional preferred combination of substituents provides a compound of formula (I) wherein R ¹ is methyl, -CH2-C=CH, or cyclopropyl; R ² is methyl, G is H, -C(O)methyl, -C(O)'Pr, -C(O)'-Bu, -C(O)O-methyl, -C(O)OtBu , -C(O)-4-morpholino or -C(O)-phenyl; X is hydrogen, halogen or C1-haloalkyl; Y is hydrogen or halogen; W represents -CH ₂ -CH ₂ -, (E)-CH-CH- or -C=C-; D is either Dp, where Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are each independently selected from the group consisting of hydrogen, cyano, amino, dimethylamino, hydroxy, methyl, methoxy, halomethyl, C1-C3- haloalkoxy and halogen, or D is a substituted or unsubstituted pyridyl, pyrazolyl, thiazolyl, pyrimidinyl or thienyl ring, wherein, if the ring is substituted, it is substituted with 1 or 2 R ⁸ ; and each R ⁸ is independently selected from the group consisting of halogen, amino, -NHC(O)C1-C ₃ -alkyl, methyl, and halomethyl.

Another preferred combination of substituents provides a compound of formula (I) wherein R ¹ is methyl, -CH2-C=CH or cyclopropyl; R ² is methyl, G is H or —C(O)'Pg; X is hydrogen, halogen or C1-haloalkyl; Y is hydrogen or halogen; W is -CH2-CH ₂ - or (E)-CH-CH-; D is either Dp, where Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are each independently selected from the group consisting of hydrogen, cyano, halo, C1-C3 alkyl or C1-C3 haloalkyl, or D is a substituted or unsubstituted pyridyl or thiazolyl ring, wherein, if the ring is substituted, it is substituted with 1 or 2 R ⁸ ; and each R ⁸ is independently selected from the group consisting of halo, C1-C3 alkyl or CrC ₃ haloalkyl.

Another preferred combination of substituents provides a compound of formula (I) wherein R ¹ is methyl, -CH2-C=CH or cyclopropyl; R ² is methyl, G is H or —C(O)'Pg; X is fluorine or chlorine; Y represents hydrogen or chlorine; W represents -CH ₂ -CH ₂ - or (E)-CH-CH-; D is either Dp where Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ are each independently selected from the group consisting of hydrogen, cyano, halogen, methyl or halomethyl, or D is substituted or unsubstituted pyridyl or thiazolyl a ring, wherein, if the ring is substituted, it is substituted with 1 or 2 R ⁸ ; and each R ⁸ is independently selected from the group consisting of halo, methyl and halomethyl.

Typical abbreviations used in this document include the following:

br=wide Dba;

^t Bu=tert-butyl;

d=dulet;

dba=dibenzylideneacetone;

DCM=dichloromethane;

DMSO=dimethylsulfoxide;

DPPA=diphenylphosphoryl azide;

E1 ₂ O=diethyl ether;

EtOAc=ethyl acetate;

m=multiplet;

Me=methyl;

MeOH=methanol;

Ph=phenyl;

'Pr=isopropyl;

RT = room temperature;

s=singlet;

- 48 040613 t=triplet;

THF=tetrahydrofuran.

Compounds of the present invention can be prepared according to the following schemes, in which the substituents R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁸ , R ⁹ , R 10 , R ¹¹ , R ¹² , ^{R 13} , R ¹⁴ , R ¹⁵ , W, D, Dp, G, X, Y, Z ¹ , Z ² , Z ³ ,

Z ⁴ , Z ⁵ and m have (unless explicitly stated otherwise) the definitions described in this document above.

Some compounds (I-ii) of the present invention can be obtained from compounds (2) as shown in Reaction Scheme 1. Compounds (I-ii) are compounds of formula (I) in which W is -CH ₂ -CH ₂ -.

Reaction Scheme 1

Compounds (I-ii) can be obtained by catalytic hydrogenation of compounds (2) with hydrogen gas in a suitable solvent (such as tetrahydrofuran, methanol, ethanol, acetic acid or ethyl acetate) in the presence of a suitable catalyst (such as Pd/C, Pd/CaCO ₃ , Rh/Al ₂ CO ₃ or spongy nickel) at -10 to 100°C.

Compounds (2) can be prepared from compounds (3) and compounds (4) as shown in Reaction Scheme 2, according to either the described Suzuki reaction protocol or the described Heck reaction protocol. When using the Suzuki reaction protocol, the compounds (4) are organoboron compounds such as boronic acids, boronic esters or potassium trifluoroborate salts. Compounds (4) are styrenes when using the Heck reaction protocol.

⁽³ > J = [B] or H (2)

Reaction Scheme 2

Suzuki reaction protocol.

Compounds (2) can be obtained by treating compounds (3) with compounds (4) in the presence of a suitable base and a suitable catalyst in a suitable solvent at a temperature of from 10 to 150°C. Examples of suitable bases include potassium carbonate, potassium phosphate, sodium carbonate, sodium bicarbonate and potassium fluoride. Examples of suitable catalysts include [1,H-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl ₂ (dppf)-DCM], tetrakis(triphenylphosphine)palladium(0) [Pd(PPh ₃ ) ₄ ] and catalytic a system formed in situ from a mixture of palladium(II) acetate and triphenylphosphine. Examples of suitable solvents include 1,4-dioxane, tetrahydrofuran, acetonitrile and toluene. Many compounds (4) are commercially available (such as trans-2-phenylvinylboronic acid, trans-2-(4-trifluoromethylphenyl)vinylboronic acid and trans-2-(4-chlorophenyl)vinylboronic acid) or can be prepared using known methods . Examples of compounds (3) having particular applicability in the Suzuki reaction protocol are isobutyryl esters (3-i) where G is isobutyryl.

One of skill in the art will appreciate that the conditions of the Suzuki reaction protocol may provide cleavage of ester groups, hence Reaction Scheme 2 may also describe a reaction where the starting material (3) contains an ester moiety (so G is an acyl group) but the product (2) does not contain (so G is hydrogen).

Heck reaction protocol.

Compounds (2) can be obtained by treating compounds (3) with compounds (4) in the presence of a suitable base and a suitable catalyst at a temperature of from 10 to 150°C. Optionally, an additional solvent may be included. Examples of suitable bases include triethylamine, morpholine, N-methylmorpholine, diisopropylethylamine and pyridine. Examples of suitable catalysts include tetrakis(triphenylphosphine)palladium(0) [Pd(PPh ₃ ) ₄ ], catalytic system,

- 49 040613 formed in situ from a mixture of palladium(II) acetate and triphenylphosphine, and a catalytic system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tri-tertbutylphosphonium tetrafluoroborate. Examples of the optional additional solvent include 1,4-dioxane, tetrahydrofuran, acetonitrile and toluene. Many compounds (4) are commercially available (such as 2-(trifluoromethyl)-5-vinylpyridine, 4-fluorostyrene, 4-cyanostyrene and 4-trifluoromethylstyrene) or can be prepared using known methods. Examples of compounds (3) having particular applicability in the Heck reaction protocol are isobutyryl esters (3-i) where G is isobutyryl.

Compounds (3-i) can be prepared from compounds (5) as shown in Reaction Scheme 3.

Reaction Scheme 3

Compounds (3-i) can be prepared by treating compounds (5) with isobutyryl chloride in a suitable solvent (such as dichloromethane, acetonitrile or toluene) in the presence of a suitable base (such as triethylamine, diisopropylethylamine or pyridine) at -10 to 60°C C. Optionally, a catalyst (such as 4-(dimethylamino)pyridine) may be included.

Compounds (5) can be prepared from compounds (6) as shown in Reaction Scheme 4 by heating compounds (6) with a base (such as 1,8-diazabicyclo[5.4.0]undec-7-ene, sodium hexamethyldisilazide or hexamethyldisilazide lithium) in a solvent (such as acetonitrile, N,N-dimethylformamide or toluene) at 50 to 200°C. Conventional heating or microwave heating may be used.

Reaction Scheme 4

Compounds (6) can be prepared from phenylacetic acids (7) as shown in Reaction Scheme 5. X

Reaction Scheme 5

Referring to Reaction Scheme 5, the hydrazine example (8) is methylhydrazine and the ketoester example (10) is ethyl pyruvate. An example of hydrazone (9) is ethyl (2E/Z)-2-(methylhydrazono)propanoate prepared according to the methods described in PCT Publication No. WO 2016/008816. An example of phenylacetic acid (7) is (2-bromo-6-fluorophenyl)acetic acid which can be synthesized according to Reaction Scheme 10. An additional example of phenylacetic acid (7) is (2-bromo-3-chloro-6 -fluorophenyl)acetic acid, which can be synthesized according to

- 50 040613 reaction scheme 11.

Some compounds (I-iii) of the present invention can be obtained from compounds (11) as shown in Reaction Scheme 6, or from compounds (I-iv) as shown in Reaction Scheme 12. Compounds (I-iii) are compounds formula (I), in which W represents -CH ₂ -CH ₂ - and G represents hydrogen.

Reaction Scheme 6

Compounds (I-iii) can be prepared by heating compounds (11) with a base (such as 1,8-diazabicyclo[5.4.0]undec-7-ene, sodium hexamethyldisilazide or lithium hexamethyldisilazide) in a solvent (such as acetonitrile, N, N-dimethylformamide or toluene) at 50 to 200°C. Conventional heating or microwave heating may be used.

X

Reaction Scheme 7

Compounds (11) can be prepared from compounds (12) as shown in Reaction Scheme 7 above.

Compounds (12) can be prepared from compounds (13) as shown in Reaction Scheme 8. Many compounds (13) are commercially available (such as methyl-2-phenylacetate and methyl-2-(2fluorophenyl)acetate).

X

- 51 040613

Reaction Scheme 8

With respect to Reaction Scheme 8, phosphoranes (15) can be prepared according to Reaction Scheme 9.

Reaction Scheme 9

With respect to Reaction Scheme 9, examples of suitable bases are sodium hydride, sodium hexamethyldisilazide, and potassium tert-butoxide. Compounds (16) are electrophiles where LG is a leaving group (such as chloride, bromide, iodide, tosylate or mesylate). Many compounds (16) are commercially available (such as 4-chlorobenzyl bromide or 2-chloro-5-chloromethylthiazole).

Reaction Scheme 10

With respect to Reaction Scheme 10, (2-bromo-6-fluorophenyl)acetic acid ethyl ester can be prepared as described in Lundgren et al. JACS 2016, 138, 13826-13829.

2-methylbut-2-ene

NaH ₂ PO ₄ tert-butanol water

Reaction Scheme 11

With respect to Reaction Scheme 11, 2-bromo-1-chloro-4-fluoro-benzene is commercially available. O

(l-iv) (l-iii)

Reaction Scheme 12

Compounds (I-iii) can be obtained by treating compounds (I-iv) with a metal hydroxide (such as sodium hydroxide, lithium hydroxide or potassium hydroxide) in a mixture of water and an alcoholic solvent (such as methanol or ethanol) at a temperature of 0 to 100° C. Compounds (I-iv) are compounds of formula (I) in which W is —CH ₂ —CH ₂ — and G is C(O)R ³ .

Compounds (2) can be prepared from compounds (14) and compounds (15) as shown in Reaction Scheme 13 according to either the described Suzuki reaction protocol or the described Heck reaction protocol. When using the Suzuki reaction protocol, compounds (14) are organoboron compounds such as boronic acids, boronic esters or potassium trifluoroborate salts, and compounds (15) are halide or pseudohalide compounds such as chlorides, bromides, iodides or triflates. When using the Heck reaction protocol, compounds (14) are styrenes and compounds (15) are halide or pseudohalide compounds such as chlorides, bromides, iodides or triflates.

- 52 040613

pseudohalide

Reaction Scheme 13

Suzuki reaction protocol.

Compounds (2) can be obtained by treating compounds (14) with compounds (15) in the presence of a suitable base and a suitable catalyst in a suitable solvent at a temperature of from 10 to 150°C. Examples of suitable bases include potassium carbonate, potassium phosphate, sodium carbonate, sodium bicarbonate and potassium fluoride. Examples of suitable catalysts include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex [PdCl ₂ (dppf)-DCM], tetrakis(triphenylphosphine)palladium(0) [Pd(PPh ₃ ) ₄ ], and a catalytic system formed in situ from a mixture of palladium(II) acetate and triphenylphosphine. Examples of suitable solvents include 1,4-dioxane, tetrahydrofuran, acetonitrile and toluene. Many compounds (15) are commercially available or can be obtained using known methods. Examples of compounds (14) having particular applicability in the Suzuki reaction protocol are isobutyryl esters (14-i) where G is isobutyryl.

One of skill in the art will appreciate that the conditions of the Suzuki reaction protocol may provide cleavage of ester groups, hence Reaction Scheme 13 may also describe a reaction where the starting material (14) contains an ester moiety (so G is an acyl group) but the product (2) does not contain (so G is hydrogen).

Heck reaction protocol.

Compounds (2) can be obtained by treating compounds (14) with compounds (15) in the presence of a suitable base and a suitable catalyst at a temperature of from 10 to 150°C. Optionally, an additional solvent may be included. Examples of suitable bases include triethylamine, morpholine, N-methylmorpholine, diisopropylethylamine and pyridine. Examples of suitable catalysts include tetrakis(triphenylphosphine)palladium(0) [Pd(PPh ₃ ) ₄ ], a catalyst system formed in situ from a mixture of palladium(P) acetate and triphenylphosphine, and a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone) dipalladium(0) and tritert-butylphosphonium tetrafluoroborate. Examples of the optional additional solvent include 1,4-dioxane, tetrahydrofuran, acetonitrile and toluene. Many compounds (15) are commercially available or can be obtained using known methods. Examples of compounds (14) having particular applicability in the Heck reaction protocol are isobutyryl esters (14-i) where G is isobutyryl.

Compounds (14-ii) where J is an organoboron compound such as a boronic ester can be prepared from compounds (3) and compounds (16) as shown in Reaction Scheme 14.

(3) J = [V] (14-ii)

Reaction Scheme 14

Compounds (14-ii) can be obtained by treating compounds (3) with compounds (16) in the presence of a suitable base and a suitable catalyst at a temperature of from 10 to 150°C. Optionally, an additional solvent may be included. Examples of suitable bases include triethylamine, morpholine, N-methylmorpholine, diisopropylethylamine and pyridine. Examples of suitable catalysts include tetrakis(triphenylphosphine)palladium(0) [Pd(PPh ₃ ) ₄ ], a catalyst system formed in situ from a mixture of palladium(P) acetate and triphenylphosphine, and a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone) dipalladium(0) and tritert-butylphosphonium tetrafluoroborate. Examples of the optional additional solvent include 1,4-dioxane, tetrahydrofuran, acetonitrile and toluene. Many compounds (16) are commercially available, such as vinylboronic acid MIDA ester or vinylboronic acid pinacol ester, or can be prepared by known methods. Connection examples (3),

- 53 040613 characterized by particular applicability in the Heck reaction protocol, are isobutyryl esters (3-i), where G is isobutyryl.

Compounds (14-iii) where J is hydrogen can be prepared from compounds (3) as shown in Reaction Scheme 15.

X

(3) J = H (14-iii)

Reaction Scheme 15

Compounds (14-iii) can be obtained by treating compounds (3) with tributyl(vinyl)stannan, optionally in the presence of a suitable base, in the presence of a suitable catalyst at a temperature of from 10 to 150°C in a suitable solvent. Examples of optional bases include triethylamine, morpholine, N-methylmorpholine, diisopropylethylamine, and pyridine. Examples of suitable catalysts include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex [PdCl2(dppf)-DCM], tetrakis(triphenylphosphine)palladium(0) [Pd(PPh ₃ ) ₄ ], catalytic a system formed in situ from a mixture of palladium(II) acetate and triphenylphosphine, a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tri-tert-butylphosphonium tetrafluoroborate, and a catalyst system formed in situ from a palladium cyclic precatalyst, such as chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II). Examples of suitable solvents include 1,4-dioxane, tetrahydrofuran, acetonitrile and toluene. Examples of compounds (3) having particular applicability are isobutyryl esters (3-i), where G is isobutyryl.

Compounds (18) can be prepared from compounds (3) via the Sonogashira reaction as shown in Reaction Scheme 16.

Reaction Scheme 16

Compounds (18) can be obtained by treating compounds (3) with compounds (17) in the presence of a suitable base and suitable(their) catalyst(s) at a temperature of from 10 to 150°C. Optionally, additional solvent may be added. Examples of suitable bases include triethylamine, morpholine, N-methylmorpholine, diisopropylamine, diisopropylethylamine and pyridine. Examples of suitable catalysts include bis(triphenylphosphine)palladium(P) dichloride [Pd(PPh ₃ )Cl ₂ ], a catalyst system formed in situ from a mixture of palladium(P) acetate and triphenylphosphine, a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone )dipalladium(0) and tri-tert-butylphosphonium tetrafluoroborate, and a catalyst system formed in situ from a palladium cyclic pre-catalyst such as chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II). Optionally, copper catalysts such as copper(I) iodide may also be added. Examples of suitable additional solvents include 1,4-dioxane, tetrahydrofuran, acetonitrile, toluene and N,N-dimethylformamide. Examples of compounds (3) having particular applicability are isobutyryl esters (3-i), where G is isobutyryl.

One of skill in the art will appreciate that the Sonogashira reaction conditions can provide cleavage of ester groups, so Reaction Scheme 16 can also describe a reaction where the starting material (3) contains an ester moiety (so G is an acyl group) but the product (18 ) does not contain (so G is hydrogen).

Compounds (19) can be prepared from compounds (3) and compounds (20) as shown in Reaction Scheme 17 by a Suzuki reaction, where compound (20) is a suitable organoboron compound such as boric acid, a boronate ester or a salt, which is potassium trifluoroborate.

- 54 040613

J

(3) J = [V] (19)

Reaction Scheme 17

Compounds (19) can be obtained by treating compounds (3) with compounds (20) in the presence of a suitable base and a suitable catalyst in a suitable solvent at a temperature of from 10 to 150°C. Examples of suitable bases include potassium carbonate, potassium phosphate, sodium carbonate, sodium bicarbonate and potassium fluoride. Examples of suitable catalysts include [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane [PdCl ₂ (dppf)-DCM] complex, a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tri-tert-butylphosphonium tetrafluoroborate, a catalyst system formed in situ from a mixture of tris(dibenzylideneacetone)dipalladium(0) and tricyclohexylphosphine, a catalyst system formed in situ from a palladium cyclic precatalyst such as chloro[(tri-tert-butylphosphine)-2( 2-aminobiphenyl)]palladium(II), and a catalyst system formed in situ from a palladium cyclic pre-catalyst such as chloro[(tricyclohexylphosphine)-2-(2'-aminobiphenyl)]palladium(II). Examples of suitable solvents include 1,4-dioxane, tetrahydrofuran, acetonitrile and toluene. Some compounds (20) are commercially available (for example, 4,4,5,5-tetramethyl-2-(2-phenylcyclopropyl)-[1,3,2]dioxaborolane) or can be prepared using known methods (see, for example, methods described in Org. Process Res. Dev. 2012, 16, 87-95). Examples of compounds (3) having particular utility in the Suzuki reaction are benzyl esters (3-ii), where G is benzyl.

(19-i) (19-ii)

Reaction Scheme 18

Compounds (19-ii) can be obtained by catalytic hydrogenation of compounds (19-i) with hydrogen gas in a suitable solvent (such as tetrahydrofuran, methanol, ethanol, acetic acid or ethyl acetate) in the presence of a suitable catalyst (such as Pd/C, Pd /CaCO ₃ , Rh/Al ₂ CO ₃ or nickel sponge) at -10 to 100°C.

One skilled in the art will appreciate that some of the intermediates described herein are also novel, and as such they form additional aspects of the present invention. In particular, some of the compounds (7), (7a) and (12) are new and the present invention thus covers the compounds of formulas (7), (7a) and (12) as defined in the schemes above.

The compounds of formula (I) according to the present invention can be used alone as herbicides, but are usually formulated into herbicidal compositions using formulation aids such as carriers, solvents and surface active agents (SFA). Thus, the present invention further provides a herbicidal composition comprising a herbicidal compound according to any one of the claims and an agriculturally acceptable formulation aid. The composition may be presented in the form of concentrates which are diluted prior to use, although ready-to-use compositions may also be obtained. Final dilution is usually performed using water, but it can also be performed using liquid fertilizers, micronutrients, biological organisms, oils or solvents instead of water or in addition to water.

Herbicidal compositions generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight of the compounds of formula (I) and from 1 to 99.9% by weight of a formulation aid, which is preferably includes from 0 to 25% by weight of a surfactant.

Compositions may be selected from a variety of formulation types, many of which are known from the FAO Specifications Development and Application Manual for Crop Protection Products.

- 55 040613

Development and Use of FAO Specifications for Plant Protection Products, 5th Edition, 1999). These include sprayable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL ), oil-miscible fluids (OL), ultra-low volume fluids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil-in-water (EW) and water-in-oil ( EO)), microemulsions (ME), suspension concentrates (SC), aerosols, capsule suspensions (CS) and seed treatments. The type of composition chosen will in any event depend on the particular intended use and the physical, chemical and biological properties of the compound of formula (I).

Sprayable powders (DP) can be obtained by mixing a compound of formula (I) with one or more solid diluents (for example, natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earth, calcium phosphates, calcium and magnesium carbonates , sulfur, lime, fine powders, talc and other organic and inorganic solid carriers) and mechanical grinding of the mixture into a fine powder.

Soluble powders (SP) can be prepared by mixing a compound of formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or with one or more water-soluble organic solids (such as a polysaccharide ) and optionally with one or more wetting agents, one or more dispersing agents, or a mixture of these agents to improve water dispersibility/solubility. The mixture is then ground to a fine powder. Such compositions can also be granulated to form water soluble granules (SG).

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

Granules (GR) may be formed either by granulating a mixture of a compound of formula (I) and one or more powdery solid diluents or carriers, or from previously formed empty granules by absorbing a compound of formula (I) (or a solution thereof in a suitable vehicle) into a porous granular material (such as pumice, attapulgite clays, fuller's earth, diatomaceous earth, diatomaceous earth or crushed corn cobs) or by adsorption of the compound of formula (I) (or its solution in a suitable medium) on a hard granular material (such as sands, silicates, mineral carbonates , sulfates or phosphates) and drying if necessary. Agents commonly used to facilitate absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones, and esters) and tackifiers (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars, and vegetable oils). oils). One or more other additives (eg, an emulsifying agent, wetting agent, or dispersing agent) may also be included in the granules.

Dispersible concentrates (DC) can be prepared by dissolving a compound of formula (I) in water or an organic solvent such as a ketone, alcohol or glycol ether. These solutions may contain a surfactant (for example, to improve dilution with water or prevent crystallization in the spray tank).

Emulsifiable concentrates (EC) or oil-in-water (EW) emulsions can be prepared by dissolving a compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents, or a mixture of these agents). Suitable organic solvents for use in the EU include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, such as SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO being a registered trademark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), fatty acid dimethylamides (such as C ₈ -C _1o fatty acid dimethylamide), and chlorinated hydrocarbons. The EC product can spontaneously emulsify when added to water to provide an emulsion that is stable enough to be spray applied with suitable equipment.

The preparation of EW involves the preparation of a compound of formula (I) either as a liquid (if it is not a liquid at room temperature, it can be melted at an acceptable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifying the resulting liquid or solution in water containing one or more SFAs,

- 56 040613 with high shear to form an emulsion. Suitable solvents for use in EW include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes), and other suitable organic solvents that have low water solubility.

Microemulsions (ME) can be prepared by mixing water with a mixture of one or more solvents with one or more SFAs to spontaneously form a thermodynamically stable isotropic liquid composition. The compound of formula (I) is initially present either in water or in a solvent/SFA mixture. Suitable solvents for use in ME include the solvents described herein above for use in the EU or EW. The ME may be either an oil-in-water or a water-in-oil system (whereby the system may be determined by electrical conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. ME is suitable for dilution in water, while it either remains in the form of a microemulsion or forms a conventional oil-in-water emulsion.

Suspension concentrates (SC) may contain aqueous or non-aqueous suspensions of finely divided insoluble solid particles of the compound of formula (I). SC can be obtained by grinding in a ball or bead mill a solid compound of formula (I) in a suitable medium, optionally with one or more dispersants, to obtain a fine suspension of the compound. One or more wetting agents may be included in the composition, and a suspending agent may also be included to reduce the settling rate of the particles. Alternatively, the compound of formula (I) can be dry-milled and added to water containing the agents described herein above to obtain the desired end product.

Aerosol formulations contain a compound of formula (I) and a suitable propellant (eg n-butane). The compound of formula (I) can also be dissolved or dispersed in a suitable medium (eg water or a water-miscible liquid such as n-propanol) to provide compositions for use in non-pressurized manual spray pumps.

Capsule suspensions (CS) can be prepared similarly to the preparation of EW formulations, but with an additional polymerization step to obtain an aqueous dispersion of oil droplets, in which each oil droplet is encapsulated by a polymer shell and contains a compound of formula (I) and optionally its carrier or diluent. The polymer shell can be obtained either by carrying out an interfacial polycondensation reaction or by using a coacervation procedure. The compositions may provide a controlled release of a compound of formula (I) and may be used for seed treatment. The compound of formula (I) can also be formulated into a biodegradable polymer matrix to provide a slow controlled release of the compound.

The composition may include one or more additives to improve the biological performance of the composition, for example, by improving wetting, retention on surfaces or distribution on surfaces; resistance to being washed off by rain from treated surfaces; or the absorption or mobility of the compound of formula (I). Such additives include surface active agents (SFAs), oil-based spray additives such as certain mineral oils or natural vegetable oils (such as soybean and rapeseed oils), and mixtures thereof with other bioenhancing adjuvants (ingredients that may contribute to the action of compounds of formula (I) or modify it).

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

Suitable cationic type SFAs include quaternary ammonium compounds (eg, cetyltrimethylammonium bromide), imidazolines, and amine salts.

Suitable anionic SFAs include alkali metal fatty acid salts, salts of aliphatic sulfuric acid monoesters (e.g. sodium lauryl sulfate), salts of sulfonated aromatics (e.g. sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalenesulfonate and mixtures of sodium diisopropyl and triisopropylnaphthalenesulfonates), ether sulfates, alcohol ether sulfates (e.g. sodium laureth-3-sulphate), ester carboxylates (e.g. sodium laureth-3-carboxylate), phosphoric acid esters (reaction products between one or more fatty alcohols and phosphoric acid (predominantly monoesters) or phosphorus pentoxide (predominantly diesters), for example, in the reaction between lauryl alcohol and tetraphosphoric acid; in addition, these products can be ethoxylated), sulfosuccinamates, paraffin or olefin sulfonates, taurates and lignosulfonates.

Suitable amphoteric type SFAs include betaines, propionates and glycinates.

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

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

The composition of the present invention may further contain at least one additional pesticide. For example, the compounds of the present invention may also be used in combination with other herbicides or plant growth regulators. The additional pesticide may be a herbicide and/or a herbicide safener. Specific examples of such mixtures include (wherein I is a compound of formula (I)) the following: I+acetochlor; I + acifluorfen (including acifluorfen sodium); I + aclonifen; I+alachlor; I+alloxidim; I + ametrine; I+amicarbazone; I + amidosulfuron; I + aminocyclopyrachlor; I + amino pyralide; I+amitrol; I + asulam; I+atrazine; I + bensulfuron (including bensulfuron-methyl); I+bentazone; I+bicyclopyrone; I + bilanaphos; I + bifenox; I + bispyribac-sodium; I+bixlozone; I + bromacyl; I + bromoxynil; I+butachlor; I + butafenacil; I+cafenstrol; I + carfentrazone (including carfentrazone-ethyl); cloransulam (including cloransulam-methyl); I + chlorimuron (including chlorimuron-ethyl); I+chlorotoluron; I + cinosulfuron; I + chlorsulfuron; I + cinmethylin; I + claciphos; I + cletodym; I + clodinafop (including clodinafop-propargyl); I+clomazone; I+clopyralide; I+cyclopyranil; I + cyclopyrimorate; I + cyclosulfamuron; I + cyhalofop (including cyhalofop-butyl); I+2,4-D (including the choline salt and its 2-ethylhexyl ester); I+2,4-DB; I+daimuron; I+desmedifam; I + dicamba (including its salts with aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichlorprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium); I + diclofop-methyl; I+diclosulam; I + diflufenican; I+difenzoquat; I + diflufenican; I + diflufenzopyr; I+dimethachlor; I+dimethenamid-P; I + diquat dibromide; I+diuron; I+esprocarb; I + etalfluralin; I+etofumesate; I + fenoxaprop (including fenoxaprop-P-ethyl); I + phenoxasulfone; I + fenquinotrion; I+phentrazamide; I+flazasulfuron; I+florasulam; I + florpyrauxifen; I+fluazifop (including fluazifop-P-butyl); I + flucarbazone (including flucarbazone sodium); I + flufenacet; I + flumetralin; I + flumetsulam; I + flumioxazine; I + flupyrsulfuron (including flupyrsulfuron-methyl-sodium); I + fluroxypyr (including fluroxypyr-meptyl); I+fluthiacet-methyl; I + fomesafen; I + foramsulfuron; I+glufosinate (including its ammonium salt); I+glyphosate (including its diammonium, isopropylammonium and potassium salts); I + galauxifen (including galauxifen-methyl); I+halosulfuron-methyl; I + haloxyfop (including haloxyfop-methyl); I + hexazinon; I + hydantocidin; I + imazamox; I+imazapic; I + imazapyr; I+imazaquin; I + imazethapyr; I + indaziflam; I + iodosulfuron (including iodosulfuron-methyl-sodium); I + iofensulfuron; I + iofensulfuron-sodium; I + ioxynil; I+ipfencarbazone; I+isoproturon; I+isoxabene; I + isoxaflutol; I + lactofen; I + lancotrion; I+linuron; I+MCRA; I+MSRV; I+mecoprop-P; I + mefenacet; I + mesosulfuron; I + mesosulfuron-methyl; I + mesotrione; I+metamitron; I + metazachlor; I+methiozolin; I + metobromuron; I + metolachlor; I + methosulam; I+methoxuron; I+metribuzin; I+metsulfuron; I + molinate; I + napropamide; I + nicosulfuron; I + norflurazon; I+orthosulfamuron; I + oxadiargyl; I+oxadiazon; I + oxasulfuron; I + oxyfluorfen; I+paraquat dichloride; I + pendimethalin; I + penoxulam; I + phenmedifam; I + pychloram; I+picolinafen; I + pinoxaden; I + pretilachlor; I + primisulfuron-methyl; I+prodiamine; I + prometrin; I+propachlor; I+propanil; I + propaquizafop; I+profam; I+propyrisulfuron, I+propizamide; I + prosulfocarb; I + prosulfuron; I+pyraclonil; I + pyraflufen (including pyraflufen-ethyl); I + pyrasulfotol; I+pyrazolinate, I+pyrazosulfuronethyl; I+pyribenoxime; I+pyridate; I + pyrifthalide; I + pyrimisulfan, I + pyrithiobac-sodium; I + pyroxasulfone; I+pyroxulam; I+quinclorac; I+quinmerac; I + quizalofop (including quizalofop-Rethyl and quizalofop-R-tefuril); I+rimsulfuron; I + saflufenacil; I+setoxydim; I + simazine; I+Smetolachlor; I+sulcotrione; I + sulfentrazone; I + sulfosulfuron; I+tebuthiuron; I+tefuryltrione; I+tembotrione; I+terbutylazine; I+terbutrin; I+thiencarbazone; I + tifensulfuron; I + thiafenacil; I+tolpyralate; I+topramesone; I+tralkoxydim; I + triafamone; I+triallate; I + triasulfuron; I + tribenuron (including tribenuron-methyl); I+triclopyr; I + trifloxysulfuron (including trifloxysulfuron sodium); I+trifludimoxazine; I + trifluralin; I + triflusulfuron; I+tritosulfuron; 1+4-hydroxy-1methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; I+4-hydroxy-1,5-dimethyl-3-[4(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; I+5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2pyridyl]imidazolidin-2-one; I+4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; I+4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one; I+(4R) 1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methylimidazolidin-2-one; I+3-[2-(3,4-dimethoxyphenyl)-6methyl-3-oxopyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl3-oxopyridazin-4-carbonyl]-5-methylcyclohexane-1,3-dione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3oxopyridazine-4-carbonyl]cyclohexane-1,3-dione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopuridazine4-carbonyl]-5,5-dimethylcyclohexane-1,3-dione; I+6-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4

- 58 040613 carbonyl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3oxopyridazine-4-carbonyl]-5-ethylcyclohexane-1,3-dione; I+2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carbonyl]-4,4,6,6-tetramethylcyclohexane-1,3-dione; I+2-[6-cyclopropyl-2-(3,4dimethoxyphenyl)-3-oxopyridazine-4-carbonyl]-5-methylcyclohexane-1,3-dione; I+3-[6-cyclopropyl-2-(3,4dimethoxyphenyl)-3-oxopyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione; I+2-[6-cyclopropyl-2-(3,4dimethoxyphenyl)-3-oxopyridazine-4-carbonyl]-5,5-dimethylcyclohexane-1,3-dione; 1+6-[6-cyclopropyl-2(3,4-dimethoxyphenyl)-3-oxopyridazine-4-carbonyl]-2,2,4,4-tetramethylcyclohexane-1,3,5-trione; I+2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxopyridazine-4-carbonyl]cyclohexane-1,3-dione; I+4-[2-(3,4dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carbonyl]-2,2,6,6-tetramethyltetrahydropyran-3,5-dione and I+4[6-cyclopropyl- 2-(3,4-dimethoxyphenyl)-3-oxopyridazine-4-carbonyl]-2,2,6,6-tetramethyltetrahydropyran3,5-dione.

The components miscible with the compound of formula (I) may also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual, Fourteenth Edition, British Crop Protection Council, 2006.

The compound of formula (I) can also be used in mixtures with other agrochemicals such as fungicides, nematicides or insecticides, examples of which are given in The Pesticide Manual.

The mixing ratio of the compound of formula (I) and the component to be mixed is preferably from 1:100 to 1000:1.

Mixtures can advantageously be used in the formulations mentioned above (in which case the active ingredient refers to an appropriate mixture of a compound of formula (I) with the component to be mixed).

The compounds of formula (I) of the present invention may also be combined with herbicide safeners. Preferred combinations (wherein I is a compound of formula (I)) include the following: I+benoxacor, I+cloquintoset (including cloquintoset-mexil); I + cyprosulfamide; I + dichlormide; I + fenchlorazole (including fenchlorazole-ethyl); I + fenclorim; I+fluxofenim; I + furilazole I + isoxadifen (including isoxadifen-ethyl); I + mefenpyr (including mefenpyrdiethyl); I + methcamifen; I+N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide and I+oxabethrinyl.

Particularly preferred are mixtures of a compound of formula (I) with cyprosulfamide, isoxadifen (including isoxadifen-ethyl), cloquintoset (including cloquintosetmexyl) and/or N-(2-methoxybenzoyl)-4-[(methylαminokαrbonyl)αmino] benzenesulfonamide.

Antidotes for a compound of formula (I) may also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual, 14th edition (BCPC), 2006. Reference to cloquintoset-mexil also refers to its salt with lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium as disclosed in WO 02/34048, and the reference to fenchlorazole-ethyl also refers to fenchlorazole, etc.

Preferably the mixture ratio of the compound of formula (I) and antidote is from 100:1 to 1:10, in particular from 20:1 to 1:1.

The compound of formula (I) can also be used in mixtures with other agrochemicals such as fungicides, nematicides or insecticides, examples of which are given in The Pesticide Manual.

The mixing ratio of the compound of formula (I) and the component to be mixed is preferably from 1:100 to 1000:1.

Mixtures can advantageously be used in the formulations mentioned above (in which case the active ingredient refers to an appropriate mixture of a compound of formula (I) with the component to be mixed).

The present invention further provides a method for selectively controlling weeds in a locus where crop plants and weeds grow, the method comprising applying to the locus a sufficient weed control amount of the composition of the present invention. Control means the destruction, reduction or retardation of growth or the prevention or reduction of germination. Typically, the plants to be controlled are unwanted plants (weeds). Place of growth means the area in which plants grow or will grow.

The application rates of the compounds of formula (I) may vary widely and depend on the nature of the soil, the method of application (before or after emergence of seedlings; seed dressing; application in a seed furrow; no-tillage application, etc.), cultivated plant, the weed(s) to be controlled, the prevailing climatic conditions and other factors determined by the method of application, the time of application and the target crop. The compounds of formula (I) according to the present invention are usually used at a rate of 10 to 2000 g/ha, in particular 50 to 1000 g/ha.

Application is usually by spraying the composition, typically with a tractor-mounted large area sprayer, but others can also be used.

- 59 040613 methods such as pollination (for powders), drip irrigation or irrigation.

Useful plants to which the composition of the present invention may be applied include crops such as cereals such as barley and wheat, cotton, oilseed rape, sunflower, maize, rice, soybean, sugar beet, sugar cane and turf. .

Crop plants may also include trees such as fruit trees, palm trees, coconut trees or other nut crops. Also included are climbing plants such as vines, fruit bushes, orchards and vegetable crops.

It should be understood that crops also include those crops that have been made tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO-, ACCase- and HPPD-inhibitors) by conventional breeding methods or by genetic engineering. An example of a crop that has been made tolerant to imidazolinones, such as imazamox, using traditional breeding methods is Clearfield® rape (canola). Examples of crops that have been genetically engineered to tolerate herbicides include, for example, glyphosate and glufosinate resistant maize varieties commercially available under the RoundupReady® and LibertyLink® trademarks. In a particularly preferred aspect, the crop plant has been modified by genetic engineering techniques to overexpress homogentisate solanesyltransferase, as described, for example, in WO 2010/029311.

Crops should also be understood to mean those that have been genetically engineered to be resistant to harmful insects, such as Bt maize (resistant to corn borer), Bt cotton (resistant to cotton weevil), and Bt potato varieties ( resistant to the Colorado potato beetle). Examples of Bt maize are Bt 176 NK® maize hybrids (Syngenta Seeds). Bt toxin is a protein that is naturally produced by the soil bacteria Bacillus thuringiensis. Examples of toxins or transgenic plants capable of synthesizing such toxins are described in EP-A-451878, EP-A-374753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427529. Examples of transgenic plants containing one or more genes encoding insect resistance and expressing one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potato varieties), NatureGard® and Protexcta®. Plant crops or their seed material can be resistant to herbicides and at the same time resistant to being eaten by insects (gene-packaged transgenics). For example, a seed may have the ability to express the insecticidal protein Cry3 while being tolerant to glyphosate.

It should also be understood that crops include those obtained by traditional breeding or genetic engineering methods and possessing so-called added traits (eg, improved storage stability, higher nutritional value, and improved taste).

Other useful plants include lawn grass, such as on golf courses, lawns, parks and roadsides, or commercially grown for turf, and ornamental plants, such as flowers or shrubs.

The compositions can be used to control unwanted plants (generally weeds). Weeds to be controlled include both monocotyledonous species such as Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum, and dicotyledonous species, for example Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium. Weeds can also include plants that can be considered crop plants but that grow outside of the cultivated area (runaways), or that grow from seeds left over from a previous planting of another crop (self-sowing plants). Such self-seeding or runaway plants may be tolerant of certain other herbicides.

Various aspects and embodiments of the present invention will now be illustrated in more detail by way of example. It should be understood that some details can be modified without departing from the scope of the present invention.

Receipt examples

Example 1 Preparation of 4-(3-chloro-6-fluoro-2-phenethylphenyl)-5-hydroxy-2,6-dimethylpyridazin-3-one.

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1.1. 3-Allyl-2-bromo-1-chloro-4-fluorobenzene.

A solution of lithium diisopropylamide (2 M in tetrahydrofuran, 3.6 ml, 7.2 mmol) was cooled to -78° C. under N ₂ atmosphere. A solution of 2-bromo-1-chloro-4-fluorobenzene (1.0 g, 4.8 mmol) in tetrahydrofuran was added dropwise at -78°C. The mixture was stirred for 45 minutes at the same temperature before treatment with allyl bromide (0.3 ml, 5.7 mmol). The reaction was allowed to continue at -78°C for 2 h, then heated to rt. The reaction was extinguished with the help of us. NH ₄ Cl solution (aq.) and extracted with ethyl acetate. Organic matter was separated and left, then washed with saline. The organics were dried over sodium sulfate and concentrated under reduced pressure to give 3-allyl-2-bromo-1-chloro-4-fluorobenzene (1.2 g, 100%) as an oil.

¹ H NMR (400 MHz, CDCl ,) δκ 7.34-7.30 (m, 1H), 7.01-6.96 (m, 1H), 5.94-5.83 (m, 1H) , 5.10-5.00 (m, 2H), 3.64-3.58 (m, 2H).

1.2. 2-(2-Bromo-3-chloro-6-fluorophenyl)acetic acid.

A solution of 3-allyl-2-bromo-1-chloro-4-fluorobenzene (15.0 g, 60.1 mmol) in dichloromethane (200 ml) in a 2-neck flask was cooled to -78°C. The throat was connected on one side to a trap containing an aqueous solution of KI. Ozone was bubbled through the solution until the starting material was completely consumed (5 hours). Air was bubbled through the solution for 10 minutes to remove excess ozone. Dimethyl sulfide (44 mL, 601 mmol) was added and the mixture was allowed to warm to rt. The reaction was allowed to continue for 16 h at rt.

The mixture was washed with brine (2x100 ml) and the organic layer was left. The organics were dried over Na ₂ SO ₄ , filtered and concentrated under reduced pressure to give crude 2-(2-bromo-3-chloro-6-fluorophenyl)acetaldehyde (15.3 g) which was used for the next step without further purification.

Crude 2-(2-bromo-3-chloro-6-fluorophenyl)acetaldehyde (15.3 g, 60.8 mmol) was dissolved in a mixture of tert-butanol (92 ml) and water (46 ml), then cooled to 0° C. 2-methylbut-2-ene (64.5 ml, 608 mmol), sodium dihydrogen phosphate (34.6 g, 243 mmol) and sodium chlorite (16.5 g, 163 mmol) were added. The mixture was stirred for 2 h, then diluted with brine (150 ml) and 2M hydrochloric acid (150 ml). The mixture was extracted with ethyl acetate (3x100 ml). The combined organic extracts were washed with saturated aqueous sodium metabisulphite (100 ml), then dried over Na ₂ SO ₄ , filtered and concentrated under reduced pressure to give a pale yellow solid. The crude solid was dissolved in a mixture of water (100 ml) and 2.0 M NaOH (30 ml). The aqueous solution was washed with ethyl acetate (100 ml) and the organics were removed. The aqueous layer was acidified by adding concentrated hydrochloric acid (20 ml) resulting in a white slurry. The mixture was extracted with ethyl acetate (3x200 ml). The combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to give 2-(2-bromo-3-chloro-6-fluorophenyl)acetic acid (8.0 g, 49%) as a white solid.

1H NMR (400 MHz, DMSO-d6) δκ 12.79 (br.s, 1H), 7.67-7.59 (m, 1H), 7.39-7.31 (m, 1H), 3, 82(s, 2H).

1.3. 2-(2-Bromo-3-chloro-6-fluorophenyl)-N-methyl-acetohydrazide.

To a stirred solution of 2-(2-bromo-3-chloro-6-fluorophenyl)acetic acid (2.0 g, 7.5 mmol) in dichloromethane (20 ml) at 0° C. N'-ethylcarbodiimide hydrochloride [EDC.HCl] (1.4 g, 9.0 mmol) followed by dropwise addition of methylhydrazine (0.4 ml, 7.5 mmol). The temperature of the reaction mixture was maintained at 0° C. for 3 hours. The reaction was then quenched with water and extracted into dichloromethane. The organics were separated, washed with brine and dried over Na ₂ SO ₄ . Concentration under reduced pressure provided crude 2-(2-bromo-3-chloro-6-fluorophenyl)-N-methylacetohydrazide (1.8 g, 81%) which was used in the next step without further purification.

- 61 040613 ^Cl £ Τ

L / O

1H NMR (400 MHz, DMSO-d6) δH 7.59 (dd, J=8.9 and 5.4, 1H), 7.30 (t, J=8.9, 1H), 4.91 (s , 2H), 4.10 (br. s, 2H), 3.02 (s, 3H).

1.4. 2-{[2-(2-Bromo-3-chloro-6-fluorophenyl)-acetyl]-methylhydrazono}-propionic acid ethyl ester.

Ethyl pyruvate (0.7 ml, 6 .7 mmol). The reaction mixture was heated at 80°C for 4 h.

Then the reaction mixture was cooled down to rt. and evaporated it under reduced pressure. The residue was purified by silica gel column chromatography (gradient elution with ethyl acetate/hexane) to give the desired compound, 2-{[2-(2-bromo-3-chloro-6-fluorophenyl)-acetyl]-methylhydrazono}-propionic ethyl ester. acids (1.8 g, 75%) as an off-white solid.

£ x ^CO ₂ Et

1H NMR (400 MHz, CDCl3) δh 7.40-7.35 (m, 1H), 7.04-6.98 (m, 1H), 4.32 (q, J=7.1, 2H), 4.24 (s, 2H), 3.41 (s, 3H), 2.32 (s, 3H), 1.36 (t, J=7.1, 3H).

1.5. 4-(2-Bromo-3-chloro-6-fluorophenyl)-5-hydroxy-2,6-dimethylpyridazin-3-one.

2-{[2-(2-Bromo-3-chloro-6-fluorophenyl)-acetyl]-methylhydrazono}-propionic acid ethyl ester (500 mg, 1.27 mmol) was dissolved in acetonitrile (2.5 mL) and treated 1,8-diazabicyclo[5.4.0]undec-7-ene [DBU] (0.47 ml, 3.2 mmol). The mixture was heated to 125° C. with microwave radiation for 1 hour. The reaction mixture was then evaporated under reduced pressure. The residue was dissolved in water and acidified to pH 1 with 2N HCl. hydrochloric acid. The mixture was extracted with DCM, the organics were separated and washed with brine. The organic solution was dried over Na ₂ SO ₄ and concentrated under reduced pressure to give the crude product. The crude material was purified by silica gel column chromatography (gradient elution with ethyl acetate/hexane) to give 4-(2-bromo-3chloro-6-fluorophenyl)-5-hydroxy-2,6-dimethylpyridazin-3-one (340 mg, 77 .1%) as an off-white solid.

1H NMR (400 MHz, DMSO-d6) δh 11.01 (s, 1H), 7.77-7.73 (m, 1H), 7.39 (t, J=8.7, 1H), 3, 58 (s, 3H), 2.24 (s, 3H).

1.6. [5-(2-bromo-3-chloro-6-fluorophenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate.

To a stirred solution of 4-(2-bromo-3-chloro-6-fluorophenyl)-5-hydroxy-2,6-dimethylpyridazin-3one (1.4 g, 4.02 mmol) in dichloromethane (32 ml) at rt. T. triethylamine (1.1 ml, 8.06 mmol), 4-(dimethylamino)pyridine [DMAP] (49 mg, 0.40 mmol) and isobutyryl chloride (0.6 ml, 4.83 mmol) were added.

After the reaction was considered complete, the reaction mixture was diluted with dichloromethane and water. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to give the crude product. The crude material was purified by silica gel column chromatography (gradient elution with ethyl acetate/hexane) to give [5-(2-bromo-3-chloro-6-fluorophenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]- 2-methylpropanoate (1.47 g, 87%).

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1H NMR (400 MHz, CDCI3) δH 7.51-7.47 (m, 1H), 7.10-7.05 (m, 1H), 3.82 (s, 3H), 2.60-2, 55 (m, 1H), 2.25 (s, 3H), 1.02-0.98 (m, 6H).

1.7. 4-[3-chloro-6-fluoro-2-[(E)-styryl]phenyl]-5-hydroxy-2,6-dimethylpyridazin-3-one.

Solid K2CO3 (298 mg, 2.16 mmol), trans-2-phenylvinylboronic acid (213 mg, 1.43 mmol) and PdCl ₂ (dppf)-DCM (118 mg, 0.143 mmol) were placed under argon. A solution of [5-(2-bromo-3chloro-6-fluorophenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (250 mg, 0.72 mmol) in 1,4-dioxane was added (4 ml) and the mixture was stirred at 95°C for 18 hours.

The reaction mixture was evaporated directly under reduced pressure to give a residue, which was purified by silica gel column chromatography (gradient elution with ethyl acetate/hexane) to give 4-[3-chloro-6-fluoro-2-[(E)-styryl]phenyl] -5-hydroxy-2,6dimethylpyridazin-3-one (160 mg, 72%).

1H NMR (DMSO-d ₆ ) δ _H 10.8 (s, 1H), 7.62 (m, 1H), 7.37-7.24 (m, 6H), 6.94 (d, J=16 .5, 1H), 6.57 (d, J=16.5, 1H), 6.53 (s, 3H), 2.18 (s, 3H).

1.8. 4-(3-Chloro-6-fluoro-2-phenethylphenyl)-5-hydroxy-2,6-dimethylpyridazin-3-one.

A stirred mixture of 4-[3-chloro-6-fluoro-2-[(E)-styryl]phenyl]-5-hydroxy-2,6-dimethylpyridazin-3one (200 mg, 0.54 mmol) and Pd/C ( 40 mg) in tetrahydrofuran (10 ml) was treated with hydrogen supplied from a pressurized cylinder for 21 h.

The catalyst was removed by filtration, and the reaction solution was evaporated to dryness. The residue was purified by silica gel flash column chromatography (gradient elution with ethyl acetate/hexanes) to give 4-(3-chloro-6-fluoro-2-phenethylphenyl)-5-hydroxy-2,6dimethylpyridazin-3-one (110 mg, 55%) as a white solid.

1H NMR (DMSO-d6) δh 10.85 (s, 1H), 7.57-7.53 (m, 1H), 7.27-7.15 (m, 4H), 7.0 (d, J =7.2, 2H), 3.60 (s, 3H), 2.73-2.50 (m, 4H), 2.25 (s, 3H).

Example 2 Preparation of 4-[3-chloro-6-fluoro-2-[2-(4-fluorophenyl)ethyl]-phenyl]-5-hydroxy-2,6dimethylpyridazin-3-one.

2.1. [5-[3-Chloro-6-fluoro-2-[(E)-2-(4-fluorophenyl)vinyl]phenyl]-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate.

A mixture of [5-(2-bromo-3-chloro-6-fluorophenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (0.50 g, 1.20 mmol, 1.0 eq.) obtained as described in example 1, tris(dibenzylideneacetone)dipalladium(0) (27 mg, 0.030 mmol, 0.025 eq.) and tri-tert-butylphosphonium tetrafluoroborate (35 mg, 0.12 mmol, 0.1 eq.) was treated with degassed triethylamine (12 ml). 1-Fluoro-4-vinylbenzene (0.43 ml, 0.44 g, 3.59 mmol, 3.0 eq.) was added and the mixture was heated to 95° C. for 18.5 h.

Heating was stopped and LC/MS analysis showed a high degree of conversion to the target product, stilbene. The reaction mixture was diluted with dichloromethane and filtered through Celite™, washing with more dichloromethane. Liquids were concentrated to dryness. The crude product was partially purified by flash column chromatography (silica, ethyl acetate/isohexane eluent) to give the desired stilbene - [5-[3-chloro-6-Fluoro-2-[(E)- 63 040613

2-(4-fluorophenyl)vinyl]phenyl]-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (0.36 g, 0.774 mmol, 65% yield) as a colorless gum.

1H NMR (400 MHz, CDCl ₃ ) δ _H 7.45-7.41 (m, 1H), 7.35-7.30 (m, 2H), 7.04-6.98 (m, 3H), 6.93 (d 1H), 6.61 (d, 1H), 3.71 (s, 3H), 2.64 (septet, 1H), 2.23 (s, 3H), 1.09 (dd, 6H).

2.2. [5-[3-Chloro-6-fluoro-2-[2-(4-fluorophenyl)ethyl]phenyl]-1,3-dimethyl-6-oxopyridazin-4-yl]-2methylpropanoate.

[5-[3-Chloro-6-fluoro-2-[(E)-2-(4-fluorophenyl)vinyl]phenyl]-1,3-dimethyl-6-oxopyridazin-4-yl]-2methylpropanoate (130 mg , 0.283 mmol) was subjected to catalytic hydrogenation in tetrahydrofuran (3 ml) in the presence of 5% Pd/C catalyst (60 mg) at an H ₂ pressure of 3 bar.

After 1.5 h, LC/MS showed completion of the reaction. The reaction mixture was filtered through a pad of Celite™, washing with ethyl acetate. The liquids were concentrated in vacuo to give a crude residue.

The residue was adsorbed onto silica and purified by flash column chromatography (silica, ethyl acetate/isohexane as eluent) to give [5-[3-chloro-6-fluoro-2-[2(4-fluorophenyl)ethyl]phenyl]-1, 3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (85 mg, 65% yield) as a colorless gum.

1H NMR (400 MHz, CDCl ₃ ) δ _H 7.42 (dd, 1H), 7.11-7.06 (m, 2H), 6.99 (t, 1H), 6.97-6.90 ( m, 2H), 3.84 (s, 3H), 2.86-2.68 (m, 4H), 2.55 (septet, 1H), 2.26 (s, 3H), 0.98 (dd , 6H).

2.3. 4-[3-Chloro-6-fluoro-2-[2-(4-fluorophenyl)ethyl]phenyl]-5-hydroxy-2,6-dimethylpyridazin-3-one.

[5-[3-Chloro-6-fluoro-2-[2-(4-fluorophenyl)ethyl]phenyl]-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (108 mg, 0.234 mmol, 1.0 eq.) was dissolved in ethanol (7.5 ml). The mixture was treated with a solution of lithium hydroxide (17 mg, 0.703 mmol, 3.0 eq.) in water (2.5 ml). The reaction mixture was stirred at rt. within 2 hours

LC/MS showed complete conversion. The reaction mixture was concentrated in vacuo to remove ethanol. The remaining aqueous solution was acidified with 1 M HCl (30 ml) and was extracted with EtOAc (3x30 ml). The combined organics were dried over MgSO ₄ , filtered and concentrated in vacuo to give the crude product.

Purification by flash column chromatography (silica, ethyl acetate/isohexane eluent) provided 4-[3-chloro-6-fluoro-2-[2-(4-fluorophenyl)ethyl]phenyl]-5-hydroxy-2, 6dimethylpyridazin-3-one (83 mg, 91% yield) as a white solid.

1H NMR (400 MHz, CDCl ₃ ) δ _H 7.44 (dd, 1H), 7.01-6.88 (m, 5H), 5.91 (br s, 1H), 3.73 (s, 3H ), 2.81-2.65 (m, 4H), 2.30 (s, 3H).

Example 3 Preparation of 4-[3-chloro-6-fluoro-2-[2-[6-(trifluoromethyl)-3-pyridyl]ethyl]phenyl]-5-hydroxy2,6-dimethylpyridazin-3-one.

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3.1. [5-[3-Chloro-6-fluoro-2-[(E)-2-[6-(trifluoromethyl)-3-pyridyl]vinyl]phenyl]-1,3-dimethyl-6oxopyridazin-4-yl]- 2-methylpropanoate.

Triethylamine (12 ml) was sparged with nitrogen for 2 minutes. It was then added to a mixture of [5-(2bromo-3-chloro-6-fluorophenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (1.65 g, 3.95 mmol, 1 0 equiv.), obtained as described in example 1, Pd ₂ (dba) ₃ (90 mg, 0.099 mmol, 0.025 equiv.) and tri-tert-butylphosphonium tetrafluoroborate (115 mg, 0.40 mmol, 0.1 equiv.). 2-(trifluoromethyl)-5-vinylpyridine (1.71 g, 9.88 mmol, 2.5 eq) was added and the mixture was heated at 95° C. for 6 h.

The mixture was allowed to cool to room temperature, then it was diluted with dichloromethane (20 ml). The mixture was washed with hydrochloric acid (20 ml, 2.0 M). The organics were dried over MgSO ₄ , filtered and concentrated in vacuo. The crude product was purified by flash column chromatography to give [5-[3-chloro-6-fluoro-2-[(E)-2-[6-(trifluoromethyl)-3pyridyl]vinyl]phenyl]-1,3-dimethyl -6-oxopyridazin-4-yl]-2-methylpropanoate (1.41 g, 2.76 mmol, you-

1H NMR (400 MHz, CDCl3) δh 8.65 (d, J=1.6, 1H), 7.87 (dd, J=8.2 and 2.1, 1H), 7.64 (d, J =8.2, 1H), 7.47 (dd, J=8.9 and 5.0, 1H), 7.17 (d, J=16.5, 1H), 7.08 (t, J= 8.7, 1H), 6.75 (d, J=16.5, 1H), 3.71 (s, 3H), 2.66 (septet, J=7.0, 1H), 2.24 ( s, 3H), 1.11 (d, J=7.0, 3H), 1.08 (d, J=7.1, 3H).

3.2. [5-[3-Chloro-6-fluoro-2-[2-[6-(trifluoromethyl)-3-pyridyl]ethyl]phenyl]-1,3-dimethyl-6-oxopyridazin4-yl]-2-methylpropanoate.

Tetrahydrofuran (12 ml) was added to a mixture of [5-[3-chloro-6-fluoro-2-[(E)-2-[6-(trifluoromethyl)-3pyridyl]vinyl]phenyl]-1,3-dimethyl-6 -oxopyridazin-4-yl]-2-methylpropanoate (1.2 g, 2.4 mmol, 1.0 eq.) and 10% palladium on activated carbon catalyst (0.25 g) under nitrogen. The mixture was subjected to hydrogenation at a hydrogen pressure of 4 bar for 16 hours.

The mixture was filtered through Celite™, washing with more tetrahydrofuran, and the filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography to give [5-[3-chloro-6-fluoro-2-[2-[6-(trifluoromethyl)-3-pyridyl]ethyl]phenyl]-1,3dimethyl-6-oxopyridazine-4 -yl]-2-methylpropanoate (1.1 g, 91% yield) as a colorless oil.

1H NMR (400 MHz, CDCl3) 5n 8.53 (d, J=1.2, 1H), 7.69-7.63 (m, 1H), 7.62-7.55 (m, 1H), 7.44 (dd, J=8.8 and 5.1, 1H), 7.02 (t, J=8.6, 1H), 3.86 (s, 3H), 3.10-2.98 (m, 1H), 2.97-2.81 (m, 2H), 2.76-2.64 (m, 1H), 2.55 (septet, J=7.0, 1H), 2.26 (s, 3H), 0.99 (d, J=7.0, 3H), 0.95 (d, J=7.0, 3H).

3.3. 4-[3-Chloro-6-fluoro-2-[2-[6-(trifluoromethyl)-3-pyridyl]ethyl]phenyl]-5-hydroxy-2,6-dimethylpyridazin-3-one.

Lithium hydroxide (0.13 g, 5.3 mmol, 3.0 eq.) was added to a solution of [5-[3-chloro-6-fluoro-2-[2-[6(trifluoromethyl)-3-pyridyl]ethyl ]phenyl]-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (0.90 g, 1.8 mmol, 1.0 eq.) in a mixture of ethanol (13 ml) and water (4 .4 ml). The mixture was stirred at room temperature for 2 days.

The mixture was concentrated in vacuo. The mixture was acidified to pH 1 by adding hydrochloric acid (6.0 ml, 2.0 M), which led to the formation of a precipitate. The solid was isolated by filtration and redissolved in dichloromethane (40 ml). The dichloromethane solution was dried over MgSO ₄ , filtered and concentrated in vacuo to give the crude product. Purification by flash column chromatography provided the impure title compound as a white foam. The material was further purified by reverse phase column chromatography to give 4-[3-chloro-6-fluoro-2-[2-[6-(trifluoromethyl)-3pyridyl]ethyl]phenyl]-5-hydroxy-2,6-dimethylpyridazine -3-one (0.232 g, 0.525 mmol, 30% yield) as a white foam.

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Ή NMR (400 MHz, CDCl ₃ ) δ _Η 8.30 (s, 1H), 7.54 (d, J=1.2, 2H), 7.37 (dd, J=8.8 and 5.1 , 1H), 6.95 (t, J=8.5, 1H), 3.69 (s, 3H), 2.92-2.65 (m, 4H), 2.28 (s, 3H).

Example 4 Preparation of 4-[3-chloro-2-[2-(2-chloro-4-pyridyl)ethyl]-6-fluorophenyl]-5-hydroxy-2,6dimethylpyridazin-3-one.

4.1. [5-[3-Chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)vinyl]phenyl] 1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate.

[5-(2-Bromo-3-chloro-6-fluorophenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (5.00 g, 11.97 mmol, 1.0 eq .), 6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione (2.63 g, 14.36 mmol, 1.2 eq.) and chloro[(tri-tert -butylphosphine)-2-(2-aminobiphenyl)]palladium(II) (307 mg, 0.60 mmol, 0.05 eq.) was charged into a 250 ml round bottom flask equipped with a condenser, magnetic stir bar and nitrogen sparger. THF (100 mL) was added followed by N,N-diisopropylethylamine (4.2 mL, 23.94 mmol, 2.0 eq.) against nitrogen flow and the mixture heated to reflux for 3 h.

The reaction mixture was allowed to cool to room temperature, then it was diluted in DCM and filtered through Celite™, washing with additional portions of DCM. The eluent was then concentrated to dryness.

The crude product was purified by flash column chromatography to give [5-[3-chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1,3,6,2- dioxazaborocan-2-yl)vinyl]phenyl]-1,3-dimethyl6-oxopyridazin-4-yl]-2-methylpropanoate (5.91 g, 11.4 mmol, 95% yield) as an off-white solid.

1H NMR (400 MHz, DMSO-d ₆ ) δ 7.63 (dd, J=5.1, 8.9 Hz, 1H), 7.31 (t, J=8.9 Hz, 1H), 6, 65 (d, J=18.3 Hz, 1H), 5.68 (d, J=18.3 Hz, 1H), 4.24 (dd, J=11.9, 17.2 Hz, 2H), 3.95-3.83 (m, 2H), 3.70 (s, 3H), 2.66 (septet, J=7.0 Hz, 1H), 2.16 (s, 3H), 0.90 (d, J=7.0 Hz, 3H), 0.89 (d, J=7.0 Hz, 3H).

4.2. 4-[3-Chloro-2-[(E)-2-(2-chloro-4-pyridyl)vinyl]-6-fluorophenyl]-5-hydroxy-2,6-dimethylpyridazin3-one.

[5-[3-Chloro-6-fluoro-2-[(E)-2-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)vinyl]phenyl] -1,3dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (10.0 g, 19.24 mmol, 1.0 eq.), potassium carbonate (8.06 g, 3.0 eq.) and complex of [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and dichloromethane [PdCl ₂ (dppf)-DCM] (786 mg, 0.96 mmol, 0.05 eq.) was loaded into a 250 ml flask equipped with magnetic stirrer armature, condenser and nitrogen inlet. The reaction vessel was evacuated and backfilled three times with nitrogen. Acetonitrile (192 mL, deoxygenated by sparging with N ₂ (gas)) was added via cannula, followed by 4-bromo-2-chloro-pyridine (5.55 g, 1.5 eq.) and water (6. 93 ml, 20 eq.). The reaction mixture was then heated at reflux for 17 hours.

The reaction mixture was allowed to cool to room temperature, then it was concentrated in vacuo. The residue was diluted with water (50 ml) and DCM (100 ml) and the aqueous phase was carefully acidified to pH 3 by slowly adding 2 M HCl (aq.). The organic layer was separated and the aqueous phase was extracted with an additional two portions of DCM (50 ml). The combined organic extracts were dried by passing through a phase separation cartridge, then concentrated in vacuo.

The crude product was purified by flash column chromatography to give 4-[3chloro-2-[(E)-2-(2-chloro-4-pyridyl)vinyl]-6-fluorophenyl]-5-hydroxy-2,6-dimethylpyridazine -3-one (5.79 g, 74% yield) as a pink solid.

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¹ H NMR (500 MHz, DMSO-d6) δ 10.85 (br s, 1H), 8.34 (d, J=5.1 Hz, 1H), 7.63 (dd, J=5.1, 8.9 Hz, 1H), 7.54 (d, J=1.4 Hz, 1H), 7.39 (dd, J=1.4, 5.1 Hz, 1H), 7.33 (t, J=8.9Hz, 1H), 7.31(d, J=16.5Hz, 1H), 6.56(d, J=16.5Hz, 1H), 3.53(s, 3H) , 2.19 (s, 3H).

4.3. 4-[3-Chloro-2-[2-(2-chloro-4-pyridyl)ethyl]-6-fluorophenyl]-5-hydroxy-2,6-dimethylpyridazin-3-one.

4-[3-Chloro-2-[(E)-2-(2-chloro-4-pyridyl)vinyl]-6-fluorophenyl]-5-hydroxy-2,6-dimethylpyridazin-3-one (5.00 d) subjected to catalytic hydrogenation in a mixture of 2:1 EtOAc:MeOH (150 ml) in the presence of 5% catalyst Rh/Al ₂ O ₃ (1.27 g) at a pressure of H ₂ 4 bar.

After 8.5 hours, the reaction mixture was filtered through a pad of Celite™, washing with ethyl acetate/methanol (1:1). The filtrate was concentrated in vacuo to give a crude residue.

The crude product was purified by flash column chromatography to give 4-[3-chloro-2-[2-(2-chloro-4-pyridyl)ethyl]-6-fluorophenyl]-5-hydroxy-2,6-dimethylpyridazine-3 -one (2.33 g, 46% yield) as a white solid.

1H NMR (400 MHz, DMSO-d6) δ 10.83 (br s, 1H), 8.24 (d, J=5.1 Hz, 1H), 7.54 (dd, J=5.3, 8 .9 Hz, 1H), 7.23 (t, J=8.9 Hz, 1H), 7.16 (br s, 1H), 7.08 (dd, J=1.4, 5.1 Hz, 1H), 3.60 (s, 3H), 2.84-2.65 (m, 4H), 2.25 (s, 3H).

Example 5 Preparation of [5-[3-chloro-2-[(E)-2-(4-cyclopropylphenyl)vinyl]-6-fluorophenyl]-1,3-dimethyl6-oxopyridazin-4-yl]-2-methylpropanoate .

5.1. [5-(3-Chloro-6-fluoro-2-vinylphenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate.

[5-(2-Bromo-3-chloro-6-fluorophenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (4.177 g, 10.00 mmol, 1.0 eq.) and tributyl(vinyl)stannan (4.384 ml, 15.00 mmol, 1.50 eq.) were dissolved in toluene (60.00 ml), then [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex was added and dichloromethane [PdCl ₂ (dppf)-DCM] (408 mg, 0.50 mmol, 0.05 eq.). The reaction mixture was heated under reflux overnight.

The reaction mixture was allowed to cool to room temperature, then it was concentrated in vacuo. The crude product was then purified by flash column chromatography to give [5-(3-chloro-6-fluoro-2-vinylphenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate as dirty white solid (3.02 g, 83% yield).

1H NMR (400 MHz, CDCl3) δ 7.40 (dd, J=5.1, 8.7 Hz, 1H), 6.99 (t, J=8.7 Hz, 1H), 6.65 (dd , J=11.6, 17.6 Hz, 1H), 5.37-5.30 (m, 2H), 3.79 (s, 3H), 2.59 (septet, J=7.0 Hz, 1H), 2.23 (s, 3H), 1.04 (d, J=7.0 Hz, 4H), 1.03 (d, J=7.0 Hz, 1H).

5.2. [5-[3-Chloro-2-[(E)-2-(4-cyclopropylphenyl)vinyl]-6-fluorophenyl]-1,3-dimethyl-6-oxopyridazin4-yl]-2-methylpropanoate.

A stirred mixture of [5-(3-chloro-6-fluoro-2-vinylphenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (300 mg, 1.0 eq.), chloro[(tru -tert-butylphosphine)-2-(2-aminobiphenyl)]palladium(II) (21 mg, 0.05 eq.), 1-bromo-4-cyclopropylbenzene (243 mg, 1.5 eq.) and N,N -diisononullethalamine (0.29 ml, 2.0 equiv.) in toluene (5 ml) under N2 was heated under reflux for 3 hours.

The reaction mixture was allowed to cool to room temperature, then it was diluted with

- 67 040613 with DCM and filtered through a pad of Celite™ eluting with additional DCM. The filtrate was concentrated in vacuo to give the crude product.

The crude product was purified by flash column chromatography to give

[5-[3-chloro-2-[(E)-2-(4-cyclopropylphenyl)vinyl]-6-fluorophenyl]-1,3-dimethyl-6-oxopyridazin-4-yl]-2methylpropanoate (285 mg, yield 72%) as a pale yellow resin.

^{0 v 1} H NMR (400 MHz, CDCl ₃ ) δ 7.41 (dd, J=5.1, 8.9 Hz, 1H), 7.26-7.22 (m, 2H), 7.02- 6.98 (m, 2H), 6.99 (t, J=8.9 Hz, 1H), 6.93 (d, J=16.5 Hz, 1H), 6.59 (d, J=16 .5 Hz, 1H), 3.71 (s, 3H), 2.62 (septet, J=7.0 Hz, 1H), 2.19 (s, 3H), 1.87 (tt, J=5 .0, 8.4 Hz, 1H), 1.07 (d, J=7.0 Hz, 3H), 1.06 (d, J=7.0 Hz, 1H), 0.99 -0.93 (m, J=2.0, 8.4 Hz, 2H), 0.73-0.64 (m, 2H).

Example 6 Preparation of 4-[3-chloro-6-fluoro-2-(2-phenylethynyl)phenyl]-5-hydroxy-2,6-dimethylpyridazin3-one.

A stirred mixture of [5-(2-bromo-3-chloro-6-fluorophenyl)-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate (400 mg, 1.0 eq.), copper(I ) (11 mg, 0.06 eq.), chloro[(tri-tert-butylphosphine)-2-(2aminobiphenyl)]palladium(II) (37 mg, 0.075 eq.) and diisopropylamine (9 ml) were heated at 120° C for 1 h in a hermetically sealed vessel under the influence of microwave radiation.

After cooling to room temperature, the reaction mixture was concentrated in vacuo, then diluted with DCM before being filtered through a pad of Celite™. The filtrate was concentrated in vacuo to give the crude product.

The crude product was purified by reverse phase mass directed preparative HPLC to give [5-[3-chloro-6-fluoro-2-(2-phenylethynyl)phenyl]-1,3-dimethyl-6-oxopyridazin-4yl]-2 -methylpropanoate (57 mg, 14% yield).

[5-[3-Chloro-6-fluoro-2-(2-phenylethynyl)phenyl]-1,3-dimethyl-6-oxopyridazin-4-yl]-2-methylpropanoate was dissolved in ethanol (5 ml), then added water (0.9 ml) and lithium hydroxide monohydrate (15 mg, 3.0 eq.). The reaction mixture was stirred at room temperature for 2 h, then concentrated in vacuo to remove ethanol. The remaining aqueous phase was acidified to pH 3 by adding 2 M HCl, then extracted with DCM (10 ml, then 2x5 ml). The combined organics were dried by passing through a phase separation cartridge, then concentrated in vacuo to give the crude product.

The crude product was purified by flash column chromatography to give 4-[3chloro-6-fluoro-2-(2-phenylethynyl)phenyl]-5-hydroxy-2,6-dimethylpyridazin-3-one (30 mg, 69% yield) as a white solid.

1H NMR (400 MHz, CDCl ₃ ) δ ppm 7.35 (dd, J=8.00, 5.00 Hz, 1H), 7.33-7.27 (m, 5H), 6.98 (t, J=8.60 Hz, 1H), 3.71-3.63 (m, 3H), 2.32-2.26 (m, 3H).

Connections 1.0001, 1.0002, 1.0012, 1.0018, 1.0024, 1.0042, 1.0048, 1.0054, 1.0060, 1.0066, 1.0072, 1.0089, 1.0101, 1.0119, 1.0095, 1.0143, 1.0125, 1.0327, 1.0333, 1.0339, 1.0345, 1.0351, 1.036, 1.036, 1.036, 1.036, 1.036, 1.036, 1,1063 , .0375, 1.0387, 1.0417, 1.0429, 1.0441, 1.0597, 1.0603, 1.0609, 1.0615, 1.0621, 1.0627, 1.0633, 1.0639, 1.0645, .0651, 1.0657, 1.0663, 1.0669, 1.0675, 1.0681, 1.0687, 1.0693, 1.0789, 1.0885 , 1.0891, 1.0897, 1.0903, 1.0915, .0921, 1.0933, 1.0149, 1.0969, 1.0975, 1.0975, 1.0981, 1.0993, 1.0999, 1.1005, 1.1011, 1.11.15

1.1258 1.1259 1.1261 1.1265 1.1267 1.1269 1.1270 1.1271 1.1282 1.1293 1.1294 1.1348 1.1351 1.1352

1.1357 1.1363 1.1367 1.1369 1.1370 1.1371 1.1372 1.1373 1.1383 1.1387 1.1391 1.1392 1.1393 1.1394

1.1447, 1.1454, 1.1457, 1.1458, 1.1556, 1.1560, 1.1651, 1.1652, 1.1653, 1.1654, 1.1655, 1.1656 were obtained using the general methods described above. In table. 2 below shows the structure of these compounds and NMR data characterizing them.

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table 2

Examples for the preparation of compounds of formula (I)

Rs Z=<CD /\f z Λ—O Λ Jr J- ^Y z S. w o (d) (I) Comm. R ¹ R ² G X Y w D Detailed NMR data 1.001 -Me -Me -Η 6-F 3-C1 -CH ₂ -CH ₂ - -Ph 'H NMR (DMSO-d6) δ _Η : 10.85 (s, 1H), 7.57-7.53 (m, 1H), 7.27-7.15 (m, 4H), 7, 0 (d, >7.2, 2H), 3.60 (s, 3H), 2.732.50 (m, 4H), 2.25 (s, 3H). 1.0002 -Me -Me -H 6-F 3-C1 (% - CH=CH- -Ph 'H NMR (DMSO-d6) 5n: 10.8 (s, 1H), 7.62 (m, 1H), 7.377.24 (m, 6H), 6.94 (d, >16.5, 1H), 6.57 (d, >16.5, 1H ), 6.53 (s, 3H), 2.18 (s, 3H). 1.0012 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-chloro-H NMR (400 MHz, phenyl-chloroform) δ = 7.51 - 7.44 (br, 1H), 7.21 - 7.15 (br, 2H), 7.07 - 6.98 (br, 1H), 6.93 (d , >8.4 Hz, 2H), 5.43 - 5.18 (br, 1H), 3.76 (s, ZH), 2.86 - 2.67 (m, 4H), 2.31 (s , ZN). 1.0018 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-tri- ^X H NMR (400 MHz, CDC1 ₃ ) δ fluoro ppm 2.29 (d, >4.16 Hz, 3 Η) methyl- 2.70 - 2.93 (m, 4 Η) 3, 65 phenyl- 3.81 (m, 3 Η) 6.95 - 7.06 (m, 1 Η) 7.12 (br d, >6.48 Hz, 2 Η) 7.48 (d, >8, 07 Hz, 3 H). 1.0024 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyano- 'Η NMR (400 MHz, CDC13) δ nopheno- ppm 7.46 - 7.51 (m, 2 Η) 7.26 nil- - 7.31 (m, 1 Η) 7.08 (d, >8.19 Hz, 2 H) 6.86 (1, >8.50 Hz, 1 H) 3.63 (s, 3 H) 2.61 - 2.77 (m, 4 H) 2.24 (s, 3 H) ). 1.0042 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4-tri- ^{X H} NMR (400 MHz, CDC1 ₃ ) δ fluoro- = 8.30 (s, 1H), 7.54 (d, J = 1.2, methyl- 2H), 7.37 (dd, J = 8.8 and 5.1, 3-pi-1H), 6.95 (t, J = 8.5, 1H), 3.69

- 69 040613 ridyl- (s, 3H), 2.92-2.65 (m, 4H), 2.28 (s, 3H).

1.0048 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 4fluorophenyl- Ή NMR (400 MHz, CDC1 ₃ ) δ ppm 7.44 (dd, 1H), 7.01-6.88 (m, 5H), 5.91 (br s, 1H), 3.73 (s, 3H ), 2.81-2.65 (m, 4H), 2.30 (s, 3H). 1.0054 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3- pyri- dil- 'H NMR (400 MHz, DMSOd6) δ ppm 2.26 (s, 3 H) 2.58 2.82 (m, 4 H) 3.61 (s, 3 H) 7.22 (t, J=8 .80 Hz, 1 H) 7.26 7.32 (m, 1 H) 7.46 (dt, J=7.79, 1.79 Hz, 1 H) 7.43 - 7.49 (m, 1 H) 7.53 (dd, J=8.86, 5.20 Hz, 1 H) 8.24 (s, 1 H) 8.40 (br d, J=3.79 Hz, 1 H). 1.0060 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 3,4-difluorophenyl- 'H NMR (400 MHz, CDC1 ₃ ) δ = 7.44 (dd, J=5.2, 8.6 Hz, 1H), 7.04 - 6.95 (m, 2H), 6.86 6.77 (m, 1H), 6.77 - 6.63 (m, 1H), 3.78 - 3.70 (m, 3H), 2.83 - 2.64 (m, 4H), 2.31 (s , 3H). 1.0066 -Me -Me -H 6-F 3-C1 -CH ₂ -CH ₂ - 2-trifluoro- methylphenyl- 'H NMR (400 MHz, CDC1 ₃ ) δ = 7.53 (br. d, J=7.5 Hz, 1H), 7.43 (br. t, J=7.5 Hz, 1H), 7.33 (dd, J=5.l, 8.5 Hz, 1H), 7.29 7.22 (m, 2H), 6.89 (t, J=8.5 Hz, 1H), 3.65 (s , 3H), 2.83 2.65 (m, 4H), 2.26 (s, 3H). 1.0072 -Me -Me (C=O/P r 6-F 3-C1 -CH ₂ -CH ₂ - 4-chlorophenyl- 'H NMR (400MHz, CDC1 ₃ ) δ = 7.41 (dd, J=5,l, 8.9Hz, 1H), 7.23 - 7.18 (m, 2H), 7.07 7.03 (m, 2H), 6.98 (t, J=8.6 Hz, 1H), 3.83 (s, 3H), 2.86 2.67 (m, 4H), 2.54 (m, 1H ), 2.24 (s, 3H), 0.97 (d, J=7.0 Hz, ZN), 0.96 (d, J=7.0 Hz, ZN). 1.0089 -Me -Me - 6-F 3-C1 -CH ₂ -CH ₂ - 4-chloro- 'H NMR (400 MHz, CDC1 ₃ ) δ

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(C=O)'P phenyl- = 7.41 (dd, J=5, l, 8.9 Hz, 1H), 1.0101-Me r -me- 6-F 3-C1 -CH ₂ -CH ₂ - 4- 7.23 - 7.18 (br, 2H), 7.07 7.03 (t, 2H), 6.98 (1, J=8.6 Hz, 1H), 3.83 (s, 3H), 2.86 2.67 (t, 4H), 2.54 (t, 1H), 2.24 (s, ZN), 0.97 (d, J=7.0 Hz, ZN), 0.96 ( d, J=7.0 Hz, ZN). 'H NMR (400 MHz, CDC1 ₃ ) δ 1.0119 -Me (C=our r -me- fluorophenyl- 6-F 3-C1 -CH ₂ -CH ₂ - 4- = 7.42 (dd, 1H), 7.11-7.06 (t, 2H), 6.99 (t, 1H), 6.97-6.90 (t, 2H), 3.84 (s , 3H), 2.862.68 (t, 4H), 2.55 (septet, 1H), 2.26 (s, 3H), 0.98 (dd, 6H). 'H NMR (400 MHz, CDCI3) δ 1.0095-Me (C=our r -me- T0LIL- 6-F 3-C1 -CH ₂ -CH ₂ - 4-tri- = 7.41 (dd, J = 8.8 & 5.1, 1H), 7.10-6.92 (m, 5H), 3.83 (s, 3H), 2.86-2.68 ( m, 4H), 2.54 (sep, J = 7.0, 1H), 2.31 (s, 3H), 2.24 (s, 3H), 0.96 (d, J = 7.0, 6H). 'H NMR (400 MHz, CDC1 ₃ ) 1.0143 -Me (C=our r -me- fluoro-methylphenyl- 6-F 3-C1 -CH ₂ -CH ₂ - 2-tri- d _H = 7.50 (d, J=8.0, 2H), 7.43 (dd, J=8.9 & 5.1, 1H), 7.24 (d, J=8.0, 2H ), 7.00 (t, J=8.6, 1H), 3.84 (s, 3H), 2.99-2.80 (m, 3H), 2.73 (dd, 1=11.0 & 6.2, 1H), 2.54 (hep, J=7.0, 1H), 2.25 (s, 3H), 0.98 (d, J=7.0, 3H), 0.95 (d, J=7.0, 3H). 'H NMR (400 MHz, (C=O)'P r fluorine- methylphenyl chloroform) δ = 7.56 (d, J=7.8 Hz, 1H), 7.49 - 7.37 (m, 3H), 7.28 (t, J=7.2 Hz, 1H), 7 .00 (t, J=8.6 Hz, 1H), 3.84 (s, 3H), 2.99 - 2.77 (m, 4H), 2.53 (septet, J=7.0 Hz, 1H), 2.26 (s, 3H), 0.96 (apparent, t,

- 71 040613

J=7.0Hz, 6H)

1.0125 -Me -Me (c=our r 6-F 3-C1 -CH ₂ -CH ₂ - 4φτορphenyl- Ή NMR (400 MHz, CDC1 ₃ ) δ = 7.42 (dd, 1H), 7.11-7.06 (m, 2H), 6.99 (t, 1H), 6.97-6.90 (m , 2H), 3.84 (s, 3H), 2.862.68 (m, 4H), 2.55 (septet, 1H), 2.26 (s, 3H), 0.98 (dd, 6H). 1.0327 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro- 4fluorophenyl 'H NMR (400 MHz, chloroform) δ = 7.34 (dd, J=5,l, 8.9Hz, 1H), 6.99 (dd, J=2.0, 7.3Hz, 1H), 6.96 (t, J=8.6Hz, 1H), 6.90(t, J=8.9Hz, 1H), 6.82(ddd, J=2.0, 4.8, 8.6Hz, 1H), 3.66 (s, 3H), 2.75 - 2.55 (m, 4H), 2.25 (s, 3H) 1.0333 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - 3-chloro- 4-pi- ridil 'H NMR (400 MHz, chloroform) δ = 8.14 (d, J=5.0 Hz, 1H), 7.38 (dd, J=5.l, 8.9 Hz, 1H), 7.01 (d, J=l, 2 Hz, 1H), 6.98 (t, J=8.9 Hz, 1H), 6.89 (dd, J=1.2, 5.0 Hz, 1H), 3.74 (s, 3H) , 2.89 2.65 (m, 4H), 2.32 (s, 3H) 1.0339 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - 4-guide- roxyphenyl 'H NMR (400 MHz, DMSOd6) δ = 10.82 (br s, 1H), 9.17 (s, 1H), 7.54 (dd, J=5.2, 8.9 Hz, 1H), 7 .20 (t, J=8.9 Hz, 1H), 6.82 - 6.75 (m, 2H), 6.65 - 6.60 (m, 2H), 3.61 (s, 3H), , 2.69 - 2.43 (m, 4H), 2.26 (s, 3H) 1.0345 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - 4-cycle 'H NMR (400 MHz,

lopro-chloroform) δ = 7.37 (dd, pil-J=5.2, 8.8 Hz, 1H), 6.96-6.88 phenyl (m, 2H), 6.91 (t, J= 8.8 Hz, 1H), 6.88 - 6.83 (t, 2H), 3.67 (s, ZN), 2.82 - 2.62 (t, 4H), 2.25 (s, ZN ), 1.84 (It, J=5.0,

- 72 040613

8.5 Hz, 1H), 0.95 - 0.88 (m, 2H), 0.68 - 0.60 (m, 2H)

1.0351 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - 1-me- til-3 - Ή NMR (400 MHz, chloroform) δ ppm 7.39 - (three- 7.27 (m, 1H), 7.08 (br s, 1H), fluorine- 6.96 - 6.79 (m, 1H), 3.86 - me- 3.76 (m, 3H), 3.71 - 3.52 (m, til)- 3H), 2.75-2.40 (m, 4H), 2.32- feast- 3.16(m, 3H) angry-4- silt 1.0357 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - thiazol- 'H NMR (400 MHz, 2-yl chloroform) δ ppm 7.38 (d, J \u003d 3.30 Hz, 1 Η), 7.16 - 7.11 (m, 2H), 6.89 (t, J=8.50 Hz, 1 Η), 3.52 - 3.39 (m, 2 Η), 3.22 - 3.08 (m, 1H), 3.06 - 2.94 (m, 1H), 2.35(s, 3H) 1.0363 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - Piri- Ή NMR (400 MHz, methanol) midin- δ = 8.95 (s, 1H), 8.46 (s, 2H), 5-yl 7.46 (dd, J = 5.2, 8.8 Hz, 1H), 7.11 (t, J = 8.7 Hz, 1H), 3.72 (s, 3H), 2.99 - 2.75 (m, 4H), 2.32(s, 3H) 1.0369 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - 4- 'H NMR (400 MHz, (tert- chloroform) δ = 7.28 (dd, J = butok- 5.2, 8.9Hz, 1H), 6.82(s, 5H), si)- 3.62 (s, 3H), 2.73 - 2.50 (m, phenyl 4H), 2.23(s, 3H) 1.0375 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - thiazol- Ή NMR (400 MHz, 5-yl chloroform) δ ppm 8.54 (s, 1 H), 7.38 (s, 2H), 7.03 - 6.91 (m, 1H), 3.70 (s, 3H), 3.04 - 2.93 (m, 2H), 2.87 - 2.79 (m, 2H), 2.28(s, 3H) 1.0387 -Me -Me - 6-F 3-C1 -CH ₂ -CH ₂ - 2-chloro- 'H NMR (400 MHz, (C=O/P 3-pi- chloroform) δ = 8.23 (dd, J = r ridil 1.9, 4.7 Hz, 1H), 7.51 (dd, J=

1.9, 7.5 Hz, 1H), 7.41 (dd, J

- 73 040613

5.1, 8.6 Hz, 1H), 7.13 (dd, J = 4.7, 7.5 Hz, 1H), 7.00 (1, J = 8.6 Hz, 1H), 3, 84 (s, ZN), 2.98 - 2.76 (m, 4H), 2.54 (septet, J = 7.0 Hz, 1H), 2.26 (s, ZN), 0.97 (d , J = 7.0 Hz, ZN), 0.96 (d, J = 7.0 Hz, 1H) 1.0417 -Me -Me (C=our r 6-F 3-C1 -CH ₂ -CH ₂ - 4-cyclopropylphenyl 'H NMR (400 MHz, chloroform) δ = 7.41 (dd, J=5.2, 8.8 Hz, 1H), 7.04 - 7.00 (m, 2H), 6.98 - 6.94 (m, 2H), 6.97 (t, J=8.8 Hz, 1H), 3.83 (s, 3H), 2.84 - 2.67 (m, 4H), 2.53 (septet, J=7.0 Hz , 1H), 2.24 (s, 3H), 1.85 (It, J=5.l, 8.4 Hz, 1H), 0.96 (d, J=7.0 Hz, ZN), 0 .96 (d, J=7.0 Hz, ZN), 0.94 0.88 (m, J=l.9, 8.5 Hz, 2H), 0.68-0.61 (m, 2H) 1.0429 -Me -Me (C=our r 6-F 3-C1 -CH ₂ -CH ₂ - thiazol- 2-yl 'H NMR (400 MHz, chloroform) δ ppm 7.65 (d, J=3.30 Hz, 1 Η), 7.43 (dd, 1=8.93, 5.14 Hz, 1 Η), 7 .17 (d, J=3.30 Hz, 1 H), 7.04 - 6.97 (m, 1H), 3.83 (s, 3H), 3.30 (ddd, J=10.82, 7.03, 5.87 Hz, 2H), 3.19 - 3006 (m, 1H), 2.98 - 2.87 (m, 1H), 2.60 2.50 (m, 1H), 2 .25 (s 3H), 0.97 (dd, 1=6.97, 2.57Hz, 6H) 1.0441 -Me -Me (C=O) ^; R r 6-F 3-C1 -CH ₂ -CH ₂ - 4- (tert-butoxy)phenyl 'H NMR (400 MHz, chloroform) δ = 7.40 (dd, J = 5.1, 8.8 Hz, 1H), 7.03 - 6.99 (m, 2H), 6.97 (t, J = 8.8 Hz, 1H), 6.90 - 6.83 (m, 2H), 3.84 (s, 3H), 2.85 - 2.68 (m, 4H), 2.55 (septet , J = 7.0 Hz, 1H), 2.25 (s, 3H), 1.32 (s, 9H), 0.97

- 74 040613

1.0597 -Me -Me H 6-F 3-C1 1.0603 -Me -Me H 6-F 3-C1 1.0609 -Me -Me H 6-F 3-C1 1.0615 -Me -Me H 6-F 3-C1 1.0621 -Me -Me H 6-F 3-C1 1.0627 -Me -Me H 6-F 3-C1

(d, J = 7.0 Hz, ZN), 0.97 (d, J

= 7.0 Hz, ZN) -CH ₂ -CH ₂ - 2- cyanophenyl 'H NMR (400 MHz, chloroform) δ = 7.51 - 7.44 (m, 2H), 7.33 - 7.24 (br, 3H + CHCl3 peak), 6.95 (1, J = 8, 6 Hz, 1H), 3.69 (s, 3H), 2.95 2.79 (br, 4H), 2.30 (s, 3H). -CH ₂ -CH ₂ - 3- cyanophenyl 'H NMR (400 MHz, chloroform) δ = 7.46 (Id, J = 1.4, 7.6 Hz, 1H), 7.37 (dd, J = 5.2, 8.9 Hz, 1H) , 7.35 - 7.28 (m, 2H), 7.26 - 7.23 (m, 1H), 6.95 (t, J = 8.6 Hz, 1H), 3.69 (s, 3H ), 2.82-2.63 (m, 4H), 2.28 (s, 3H). -CH ₂ -CH ₂ - 3-trifluoro- methylphenyl 'H NMR (400 MHz, chloroform) δ = 7.46 - 7.38 (m, 2H), 7.33 (t, J = 7.6 Hz, 1H), 7.25 - 7.16 (m, 2H), 6.98 (t, J = 8.5 Hz, 1H), 6.13 (br s, 1H), 3.71 (s, 3H), 2.92 - 2.66 (m, 4H) , 2.28 (s, 3H). -CH ₂ -CH ₂ - 0- tolil 'H NMR (400 MHz, chloroform) δ = 7.37 (dd, J = 5.1, 8.8 Hz, 1H), 7.11 - 7.02 (m, 3H), 6.97 - 6, 87 (m, 2H), 3.67 (s, 3H), 2.76-2.58 (m, 4H), 2.26 (s, 3H), 2.05 (s, 3H). -CH ₂ -CH ₂ - m- tolil 'H NMR (400 MHz, chloroform) δ = 7.40 (dd, J = 5.1, 8.8 Hz, 1H), 7.14 - 7.07 (m, 1H), 7.01 - 6, 90 (m, 2H), 6.83 - 6.74 (m, 2H), 6.21 (brd s, 1H), 3.70 (s, 3H), 2.86 2.59 (m, 4H) , 2.28 (s, 3H), 2.26 (s, 3H). -CH ₂ -CH ₂ - 2-me- til-4- 'H NMR (400 MHz, chloroform) δ ppm 8.41 (d,

- 75 040613

1.0633 -Me -Me H 6-F 3-C1 1.0639 -Me -Me H 6-F 3-C1 1.0645 -Me -Me H 6-F 3-C1 1.0651 -Me -Me H 6-F 3-C1 1.0657 -Me -Me H 6-F 3-C1

pyri- dil J=5.99 Hz, 1 H), 7.36 (dd, J=8.86, 5.07 Hz, 1 H), 7.30 (d, -CH ₂ -CH ₂ - 2-tri- J=5.99Hz, 1H), 7.23(s, 1H), 6.98(1, J=8.56Hz, 1H), 3.69(s, 3N), 3.03(s , 2H), 2.97 2.82 (m, 2H), 2.67 (s, 3H), 2.27 (s, 3H) 'H NMR (400 MHz, fluorine- chloroform) δ = 8.48 (d, J = methyl- 5.0 Hz, 1H), 7.26 (dd, J = 5.6, 4-pi- 8.5Hz, 1H), 7.26(brs, 1H), ridil 7.13 (d, J = 5.0 Hz, 1H), 6.85 -CH ₂ -CH ₂ - 2-ami- (t, J = 8.5 Hz, 1H), 3.63 (s, 3H), 2.82 - 2.69 (m, 3H), 2.69 - 2.56 (m, 1H), 2, 24(s, 3H) 'H NMR (400 MHz, DMSO- but-4- d6) δ ppm 7.73 (d, J=5.26 Hz, pyri- 1 H) 7.50 (dd, J=8.86, 5.20 DIL Hz, 1 H) 7.16 (t, J=8.62 Hz, 1 -CH ₂ -CH ₂ - 2- H) 6.18 (s, 2 H) 3.57 (s, 3 H) 2.60 - 2.69 (m, 2 H) 2.40 2.47 (m, 2 H) 2.20 (s , 3 H) 'H NMR (400 MHz, fluorine- chloroform) δ ppm 8.01 (d, 4-pi- J=5.13 Hz, 1 H) 7.42 (dd, ridil J=8.86, 5.20Hz, 1H) 6.98 - -CH ₂ -CH ₂ - 4-pi- 7.07 (m, 1 H) 6.84 - 6.90 (m, 1 H) 6.62 (s, 1 H) 3.74 (s, 3 H) 2.71 - 2.94 (m, 4H) 2.31(s, 3H) 'H NMR (400 MHz, DMSO- ridil d6) δ = 8.66 (d, J = 6.4 Hz, -CH ₂ -CH ₂ - 4- (me- 2H), 7.55 (d, J = 6.4 Hz, 2H), 7.54 (dd, J = 5.0, 8.8 Hz, 1H), 7.23 (t, J = 8.8 Hz, 1H), 3.59 (s, 3H), 2.98 - 2.75 (m, 4H), 2.26 (s, 3H) 'H NMR (400 MHz, till- chloroform) δ ppm 7.43 (dd,

- 76 040613 amino) J=8.86, 5.20 Hz, 1 H), 6.97 (t,

-phenyl 1=8.56 Hz, 1 Η), 6.81 (d,

1.0663 -Me -Me H 6-F 3-C1 1.0669 -Me -Me 6-F 3-C1 (C=O)T r

J=8.44Hz, 2H), 6.48(d, J=8.44Hz, 2H), 3.72(s, 3H), 2.80 (s, 4H), 2.75 - 2.56 (m, 3H), 2.28(s, 3H) -CH ₂ -CH ₂ - 4- 'H NMR (400 MHz, amino-chloroform) δ ppm 7.37 (dd, phenyl J=8.80, 5.26 Hz, 1 Η), 6.95 (s, 1 Η), 6.80 (d, J=8.31 Hz, 2 Η), 6.55 (d, J=8.31 Hz, 2 Η), 3.70 (s, 3 Η), 2.71 (br s, 2 Η), 2.59 (s, 2h), 2.28 (s, 3h) -CH ₂ -CH ₂ - 2- 'H NMR (400 MHz, cyanochloroform) δ = 7.56 (dd, J = phenyl 1.1, 7.7 Hz, 1H), 7.51 - 7.46 (w, 1H), 7.43 (dd, J = 5.1, 8.8 Hz, 1H), 7.32 (d, J = 7.7 Hz,

1H), 7.30 - 7.26 (m, 1H + CHC13 peak), 7.01 (t, J = 8.6 Hz, 1H), 3.85 (s, 3H), 3.15 3.05 (m, 1H), 3.04 - 2.80 (m, 3H), 2.55 (septet, J = 7.0 Hz, 1H), 2.27 (s, 3H), 0.97 (dd, J=

1.0675 -Me -Me (C=our r 6-F 3-C1 1.0681 -Me -Me (C=O/P r 6-F 3-C1

1,1,7.0 Hz, 6H). -CH ₂ -CH ₂ - 3-'H NMR (400 MHz, cyano-chloroform) δ = 7.50 - 7.46 phenyl (m, 1H), 7.46 - 7.37 (t, 3H), 7.37 - 7.31 (t, 1H), 7.00 (1, J = 8.6 Hz, 1H), 3 .86 (s, ZN), 3.00 - 2.78 (t, ZN), 2.73 2.63 (t, 1H), 2.55 (quintet, J = 7.0 Hz, 1H), 2 .26 (s, ZN), 0.97 (dd, J = 7.0, 13.5 Hz, 6H). -CH ₂ -CH ₂ - 3-tri-'H NMR (400 MHz, fluorochloroform) δ = 7.47 - 7.39 methyl- (m, 2H), 7.39 - 7.30 (t, 3H), phenyl 7.00 ( 1, J = 8.6 Hz, 1H), 3.86

- 77 040613 (s, ZN), 2.96 - 2.83 (m, ZN), 2.74 - 2.65 (m, 1H), 2.55 (septet, J = 7.0 Hz, 1H) , 2.26 (s, 3H), 0.97 (t, J = 7.2 Hz, 6H).

1.0687 -Me -Me (C=our r 6-F 3-C1 -CH ₂ -CH ₂ - 0- TOLIL Ή NMR (400 MHz, chloroform) δ = 7.43 (dd, J = 5.1, 8.8 Hz, 1H), 7.15 - 7.04 (m, 4H), 6.99 (t, J = 8.6 Hz, 1H), 3.84 (s, 3H), 2.88 - 2.64 (m, 4H), 2.54 (septet, J = 7.0 Hz, 1H), 2.25 (s, 3H), 2.18 (s, 3H), 0.96 (d, J = 7.0 Hz, 6H). 1.0693 -Me -Me (C=our r 6-F 3-C1 -CH ₂ -CH ₂ - M- TOLIL 'H NMR (400 MHz, chloroform) δ = 7.42 (dd, J = 5.1, 8.8 Hz, 1H), 7.18 - 7.11 (m, 1H), 7.02 - 6, 89 (m, 4H), 3.84 (s, 3H), 2.88 - 2.65 (m, 4H), 2.54 (septet, J = 7.0 Hz, 1H), 2.31 (s , 3H), 2.25 (s, 3H), 0.97 (d, J = 7.0 Hz, 6H). 1.0789 -Me -Me H 6-F H -CH ₂ -CH ₂ - 2- fluorine- 4-pi- ridil 'H NMR (400 MHz, chloroform) δ ppm 8.02 (d, >5.14 Hz, 1 H), 7.33 (dd, >7.89, 5.93 Hz, 1 H), 7.09 6.98(m, 2H), 6.89(d, >5.01Hz, 1H), 6.64(s, 1H), 3.76(s, 3H), 2.95-2, 68 (m, 4H), 2.33 (s, 3H) 1.0885 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - 4-(dimethylamino)-phenyl 'H NMR (400 MHz, chloroform) δ ppm 7.42 (dd, >8.80, 5.14 Hz, 1 H), 6.96 (t, >8.56 Hz, 1 H), 6.86 (d, >8.68 Hz, 2 H), 6.65 - 6.59 (m, 2H), 3.72 (s, 3H), 2.90 (s, 6H), 2.87 - 2, 80 (m, 1H), 2.77 - 2.62 (m, 3H), 2.27 (s, 3H) 1.0891 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - 3-me- 'H NMR (400 MHz,

tyl-4-chloroform) δ ppm 7.38 (dd,

- 78 040613

1.0897 -Me -Me H 6-F 3-C1 1.0903 -Me -Me H 6-F 3-C1 1.0915 -Me -Me H 6-F 3-C1 1.0921 -Me -Me H 6-F 3-C1 1.0933 -Me -Me H 6-F 3-C1

amino - J=8.86, 5.20 Hz, 1 N), 6.93 (1, phenyl J \u003d 8.56 Hz, 1 N), 6.73 - 6.59 (w, 2H), 6.52 (d, J=7.83 Hz, 1 H), 3.70 (s, ZN), 2.83 - 2.50 (w, 4H), 2.27 (s, 3H), 2.09 (s, ZN) -CH ₂ -CH ₂ -Thio- 'H NMR (400 MHz, hair dryer-3- chloroform) δ = 7.39 (dd, J = silt 5.2, 8.9 Hz, 1H), 7.19 (dd, J = 2.9, 4.9 Hz, 1H), 6.95 (t, J = 8.6 Hz, 1H), 6.84 - 6.79 (m, 1H), 6.74 (dd, J = 1.2, 4.9 Hz, 1H), 6.42(brs, 1H), 3.68(s, 3H), 2.88 - 2.63 (m, 4H), 2.27 (s, 3H). -CH ₂ -CH ₂ - 1-me- 'H NMR (400 MHz, DMSO- tilpi- d6) δ = 7.54 (dd, J = 5.3, 8.9 razol- Hz, 1H), 7.35(s, 1H), 7.20(t, 4-yl J = 8.9Hz, 1H), 7.05(s, 1H), 3.73(s, 3H), 3.59(s, 3H), 2.70 - 2.57 (m, 2H), 2.53 - 2.37 (m, 2H), 2.24(s, 3H) -CH ₂ -CH ₂ - 5-me- 'H NMR (400 MHz, till- chloroform) δppm 7.34 - 1,ZL- 7.27 (m, 1H), 7.03 -6.94 (m, oksa- 1H), 3.76 - 3.68 (m, 3H), 3.22 dia- (s, 4H), 2.47 (s, 3H), 2.36 - angry-2- 2.27(m, 3H) silt -CH ₂ -CH ₂ - 5-me- 'H NMR (400 MHz, til-3 - chloroform) δppm 7.64 - pyri- 7.84(m, 2H) 7.34(s, 1H) dil 7.09-7.19 (m, 1 H) 6.79 (brs, 1 H) 3.74 (s, 3 H) 2.65 - 2.87 (m, 4H) 2.34 (s, 3H) 2.28 (s, 3H) -CH ₂ -CH ₂ - 6-me- 'H NMR (400 MHz, til-2- chloroform) δppm 7.49 - pyri- 7.64 (m, 1 H) 7.21 (br s, 1 H)

- 79 040613 dil 6.99 (br d, J=3.67 Hz, 2 Η) 6.84 (s, 1 Η) 3.76 (s, 4 Η) 3.39 - 3.54 (m, 1 Η) 3.05 - 3.19 (m, 1 Η) 2.81 - 3.02 (m, 2 Η) 2.36 (s, 4 Η) 2.24 (br s, 3 H)

1.0149 -Me -Me - 6-F 3-C1 -CH ₂ -CH ₂ - 4- Ή NMR (400 MHz, CDC1 ₃ ) δ (C=our TOLIL- = 7.41 (dd, J = 8.8 & 5.1, 1H), r 7.10-6.92 (m, 5H), 3.83 (s, 3H), 2.86-2.68 (m, 4H), 2.54 (sep, J = 7.0, 1H), 2.31 (s, 3H), 2.24 (s, 3H), 0.96 (d, J = 7.0, 6H). 1.0969 -Me -Me - 6-F 3-C1 -CH ₂ -CH ₂ - Tno- 'H NMR (400 MHz, (C=our hair dryer-3- chloroform) δ = 7.41 (dd, J = r IL 5.1,8.8 Hz, 1H), 7.22 (dd, J = 2.9, 4.9 Hz, 1H), 6.98 (t, J = 8.6 Hz, 1H), 6, 94 - 6.91 (m, 1H), 6.88 (dd, J = 1.2, 4.9 Hz, 1H), 3.83 (s, 3H), 2.92 - 2.72 (m, 4H), 2.55 (septet, J = 7.0 Hz, 1H), 2.25 (s, 3H), 0.97 (dd, J = 3.9, 7.0 Hz, 6H). 1.0975 -Me -Me - 6-F 3-C1 -CH ₂ -CH ₂ - 1-me- 'H NMR (400 MHz, (C=our tilpi- chloroform) δ ppm 7.41 (dd, r razol- J=8.93, 5.14 Hz, 1 H), 7.21 (d, 4-yl J=2.20Hz, 1H), 6.97(t, J=8.62 Hz, 1 H), 5.95 (d, J=2.20 Hz, 1 H), 3.82 (d, .1=1.83 Hz, 6 H), 2.78 - 3.00 (m, 5 H), 2.49 - 2.62 (m, 1 H), 2.24 (s, 3 H), 0.97 (t, J=7.15Hz, 6H) 1.0975 -Me -Me - 6-F 3-C1 -CH ₂ -CH ₂ - 1-me- 'H NMR (400 MHz, (C=our tilpi- chloroform) δ = 7.40 (dd, J = r razol- 5.2, 8.9Hz, 1H), 7.23(s, 1H),

4-yl 7.10 (s, 1H), 6.97 (t, J = 8.9 Hz, 1H), 3.83 (s, 3H), 3.82 (s, 3H), 2.86 - 2.75 (tn, 1H), 2.74 - 2.59 (m, 3H), 2.55 (septet, J

- 80 040613 = 7.0 Hz, 1H), 2.24 (s, ZN), 0.98 (d, J = 7.0 Hz, ZN), 0.97

(d, J = 7.0 Hz, 1H) 1.0981 -Me -Me - (C=our G 6-F 3-C1 -CH ₂ -CH ₂ - 2-me- 'H NMR (400 MHz, tyl-chloroform) δ ppm 7.42 (dd, tri- 1 = 8.93, 5.14 Hz, 1 Η), 7.26 (s, azole-4-1 Η), 6.99 (t, J=8.62 Hz, 1 Η), or 3.83 (s, 3 Η), 4.12 (s , 3 Η), 2.72 - 3.01 (m, 4 Η), 2.47 2.63 (m, 1 Η), 2.25 (s, 3 Η), 0.97 (dd, 1= 6.97, 2.20Hz, 6H) 1.0993 -Me -Me - (C=O/P G 6-F 3-C1 -CH ₂ -CH ₂ - 5-me- 'H NMR (400 MHz, tyl-3-chloroform) δ ppm 8.25 (d, pyri- 1 = 1.47 Hz, 1 Η) 8.18 (d, dil 1=1.71 Hz, 1 H) 7.42 (dd, 1=8.80, 5.14 Hz, 1 H) 7.26 (s, 1 H) 7.00 ( 1, 1=8.62 Hz, 1 N) 3.85 (s, 3 N) 2.64 - 2.91 (br, 4 N) 2.54 (d, 1=6.97 Hz, 1 N) 2.29 (s, 3 N) 2.25 (s, 3 N) 0.97 (dd, 1=8.01, 7.03 Hz, 6 N) 1.0999 -Me -Me - (C=our G 6-F 3-C1 -CH ₂ -CH ₂ - 5-me- 'H NMR (400 MHz, tyl-2-chloroform) δ ppm 8.30 (dd, pyri- 1 \u003d 1.53, 0.67 Hz , 1 N) 7.40 dil (dd, 1=8.80, 5.14 Hz, 1 N) 7.32 - 7.37 (m, 1 N) 6.91 7.00 (m, 2 N) 3.81 (s, 3 N) 2.81 - 3.07 (m, 4 N) 2.54 (quintet, 1=6.97 Hz, 1 N) 2.28 (s, 3 N) 2.24 (s, 3 N) 0.96 (dd, 1=6.97, 5.01 Hz, 6 N) 1.1005 -Me -Me - (C=our G 6-F 3-C1 -CH ₂ -CH ₂ - 6-me-'H NMR (400 MHz, tyl-2-chloroform) δ ppm 7.36 pyri- 7.45 (m, 2 Η) 6.97 ( t, 1=8.62 dyl Hz, 1 Η) 6.93 (d, 1=7.58 Hz, 1 Η) 6.82 (d, 1=7.58 Hz, 1 Η) 3.81 (s , 3 H) 2.92 (S.4H) 2.50

2.61 (m, 1 Η) 2.47 (s, 3 Η)

- 81 040613

2.25 (s, 3 Η) 0.98 (dd, J=8.25, 7.03 Hz, 6 Η)

1.1011 -Me -Me (C=O/P r 6-F 3-C1 -CH ₂ -CH ₂ - 3-me- til-2- pyri- DIL Ή NMR (400 MHz, chloroform) δ ppm 8.34 (dd, J=4.77, 1.22 Hz, 1 H) 7.42 (dd, J=8.93, 5.14 Hz, 1 H) 7.35 (dd, J=7.58, 0.86 Hz, 1 H) 6.94 - 7.02 (m, 2 H) 3.79 1.1185 -Me -Me H 6-F 3-C1 -CH ₂ -CH ₂ - 2-acet- (s, 3 Η) 2.97 (t, J=7.95 Hz, 4 Η) 2.46 - 2.60 (m, 1 Η) 2.23 (s, 3 Η) 2.13 (s, 3 H) 0.97 (dd, J=7.03, 3.97 Hz, 6 H) 'Η NMR (400 MHz, 1.1191 -Me -Me 6-F 3-C1 -CH ₂ -CH ₂ - amidothiazole- 5-il 3,5-di- chloroform) δ ppm 7.41 (dd, J=8.86, 5.07 Hz, 1 Η) 6.97 7.03 (m, 2 Η) 3.73 (s, 3 Η) 2.84 - 3 .06 (m, 3 Η) 2.72 (s, 1 Η) 2.37 (s, 3 Η) 2.30 (s, 4 Η) 'Η NMR (400 MHz, 1.1257 -Me -Me (C=O/P r H 6-F 3-C1 (£) - fluorophenyl 2-chloro- chloroform) δ = 7.42 (dd, J = 5.1, 8.9 Hz, 1H), 6.99 (t, J = 8.9 Hz, 1H), 6.69 - 6.58 (m, 3H), 3.87 - 3.84 (m, 3H), 2.93 - 2.77 (m, 3H), 2.75 - 2.62 (m, 1H), 2.54 (septet, J = 7.0 Hz, 1H), 2.25 (s, 3H), 0.98 (d, J = 7.0 Hz, VN), 0.95 (d, J = 7.0 Hz, VN) 'H NMR (400 MHz, DMSO- 1.1258 -Me -Me H 6-F 3-C1 CH=CH- (£) - 3-pi- ridil 2-chloro- d6) δ = 10.94 (br s, 1H), 8.33 (dd, J=l.6, 4.6 Hz, 1H), 8.17 (dd, J=l.7, 7.3 Hz , 1H), 7.64 (dd, J=5, l, 8.8 Hz, 1H), 7.46 (dd, J=4.6, 7.3 Hz, 1H), 7.33 (t, J=8.8Hz, 1H), 7.17(d, J=16.5Hz, 1H), 6.76(d, J=16.5Hz, 1H), 3.53(s, 3H) , 2.19(s, 3H) 'H NMR (400 MHz,

- 82 040613

CH=CH-4-py-chloroform) δ=8.20 (d, ridyl 1=5.3 Hz, 1H), 7.29 (dd, 1=5.3, 8.5 Hz, 1H), 7 .14 (d, 1=1.3 Hz, 1H), 7.10 (d, 1=16.5 Hz, 1H), 7.05 (dd, 1=1.3, 5.3 Hz, 1H) , 6.91 (1, 1=8.5 Hz, 1H), 6.44 (d, 1=16.5 Hz, 1H), 3.61 (s, ZN), 2.24 (s, ZN)

1.1259 -Me -Me H 6-F 3-C1 (E)- CH=CH- 3-chloro- 4fluorophenyl Ή NMR (400 MHz, chloroform) δ = 7.39 (dd, 1=5.1, 8.9 Hz, 1H), 7.30 (dd, 1=2.2, 6.9 Hz, 1H), 7.11 (ddd, 1=2.2, 5.0, 8.6Hz, 1H), 7.06 (t, 1=8.6Hz, 1H), 6.97 (t, 1=8.9Hz, 1H), 6.82 (d, 1=16.5 Hz, 1H), 6.44 (d, 1=16.5 Hz, 1H), 3.63 (s, 3H), 2.24 (s, 3H) 1.1261 -Me -Me H 6-F 3-C1 (E)- CH=CH- 4-guide- roxyphenyl 'H NMR (400 MHz, DMSOd6) δ = 10.75 (br s, 1H), 9.67 (s, 1H), 7.58 (dd, 1=5.3, 8.8 Hz, 1H), 7 .23 (t, 1=8.8 Hz, 1H), 7.19 - 7.13 (m, 2H), 6.75 - 6.72 (m, 2H), 6.73 (d, 1=16 .5Hz, 1H), 6.48(d, 1=16.5Hz, 1H), 3.55(s, 3H), 2.19(s, 3H) 1.1265 -Me -Me H 6-F 3-C1 (E)- CH=CH- Piri- midin- 5-il 'H NMR (400 MHz, DMSOd6) δ = 9.08 (s, 1H), 8.86 (s, 2H), 7.63 (dd, 1=5.2, 8.9 Hz, 1H), 7, 32 (t, 1=8.9 Hz, 1H), 7.23 (d, 1=16.8 Hz, 1H), 6.60 (d, 1=16.8 Hz, 1H), 3.54 ( s, 3H), 2.19(s, 3H) 1.1267 -Me -Me H 6-F 3-C1 (E)- thiazol- 'H NMR (400 MHz,

CH=CH-5-yl chloroform) δ ppm 8.66 (s, 1 Η), 7.67 (s, 1 Η), 7.49 (dd, 1=8.86, 5.20 Hz, 1 Η ), 7.36 7.29 (m, ZN), 7.13 -7.05 (m, ZN), 6.89-6.81 (m, 1H). 6.786.63 (m, 1H), 4.77 - 4.55 (m,

- 83 040613

1.1269 -Me -Me H 6-F 3-C1 1.1270 -Me -Me H 6-F 3-C1 1.1271 -Me -Me H 6-F 3-C1 1.1282 -Me -Me H 6-F 3-C1 1.1293 -Me -Me H 6-F 3-C1

2H), 3.75(s, 3H), 2.24(s, 3H) (£) - 3- 'H NMR (400 MHz, CH=CH- cyanophenyl chloroform) δ = 7.56 - 7.47 (m, 3H), 7.44 - 7.38 (m, 2H), 7.04 - 6.93 (m, 2H), 6.53 (d, J = 16.5 Hz, 1H), 3.64 (s, ZN), 2.25 (s, ZN). (£) - 3-three- 'H NMR (400 MHz, CH=CH- fluorine- methylphenyl 0- tolil chloroform) δ = 7.55 - 7.49 (m, 2H), 7.46 - 7.39 (br, 3H), 7.05 - 6.94 (m, 2H), 6.60 (d, J = 16.4 Hz, 2H), 3.65 (s, ZN), 2.25 (s, ZN). 'H NMR (400 MHz, chloroform) δ = 7.43 (dd, J = 3.7, 5.4 Hz, 1H), 7.37 (dd, J = 5.1, 8.8 Hz, 1H) , 7.21 - 7.13 (m, 2H), 7.12 - 7.05 (m, 1H), 6.94 (t, J = 8.6 Hz, 1H), 6.84 (d, J = 1.0 Hz, 1H), 6.77 (d, J = 1.0 Hz, 1H), 6.70 (br s, 1H), 3.64 (s, 3H), 2.23 (s, 3H), 2.04 (s, 3H). (E)- Tio- 'll NMR (400 MHz, CH=CH- hair dryer-3- silt chloroform) δ = 7.39 (dd, J = 5.2, 8.9 Hz, 1H), 7.29 - 7.24 (m, 1H + CHC13 peak), 7.17 (dd, J = 1, 0, 5.0 Hz, 1H), 7.10 (dd, J = 1.1, 2.8 Hz, 1H), 6.95 (t, J = 8.6 Hz, 1H), 6.82 - 6.73 (m, 1H), 6.65-6.58 (m, 1H), 3.65 (s, 3H), 2.24 (s, 3H). (E)- 4-me- 'H NMR (400 MHz, CH=CH- til-2- pyri- DIL chloroform) δ ppm 8.09 (d, 1=5.26 Hz, 1 Η) 7.22 (d, 1=16.63 Hz, 1 Η) 7.19 (brs, 1 Η) 7.01 (dd , 1=8.74, 5.32 Hz, 1 Η) 6.95 (d, 1=5.87 Hz, 1 Η) 6.53 - 6.66 (m, 2 Η) 3.64 (s, 4

- 84 040613

H) 2.35 (d, 1=9.17Hz, 6H) 1.1294 -Me -Me H 6-F 3-C1 (£) - 2-acet- 'H NMR (400 MHz, CH=CH- amido-chloroform) δ ppm 7.44 (dd, thiazol-1=8.93, 5.14 Hz, 1 H) 7.16 5-yl 7.21 (m, 1 H) 7.04 (t, 1=8.56 Hz, 1 H) 6.71 (d, 1=4.65 Hz, 2 H) 3.72 (s, 3 H) 2.28 (s, 3 H) 2.26 (s, 3 H) 1.1348 -Me -Me - 6-F 3-C1 (£) - 4- 'H NMR (400 MHz, (C=O)‘P CH=CH- cyano-chloroform) δ = 7.62 - 7.55 g phenyl (m, 2H), 7.45 (dd, 1=5.0, 8.5 Hz, 1H), 7.45 - 7.40 (m, 1H), 7.13 (d, 1=16.5 Hz, 1H), 7.05 (1, 1=8.5 Hz, 1H), 6.68 (d, 1=16.5 Hz, 1H), 3.69 (s, 3H), 2.65 (septet, 1=7.0 Hz, 1H), 2.23 (s, 3H), 1.11 (d, 1=7.0 Hz, VN), 1.07 (d, 1=7.0 Hz, VN) 1.1351 -Me -Me - 6-F 3-C1 (£) - 4-tri- 'H NMR (400 MHz, CDC13) (C=O/P CH=CH-fluoro-δH: 8.65 (d, 1=1.6, 1H), 7.87 g methyl-(dd, 1 = 8.2 and 2.1, 1H), 7.64 3-pi- (d, 1 = 8.2, 1H), 7.47 (dd, 1 = ridyl- 8.9 and 5.0, 1H), 7.17 (d, 1 = 16.5, 1H), 7.08 (1, 1 = 8.7, 1H), 6.75 (d, 1 = 16.5, 1H), 3.71 (s, 3H), 2.66 ( septet, 1 = 7.0, 1H), 2.24 (s, 3N), 1.11 (d, 1 = 7.0, 3N), 1.08 (d, 1 = 7.1, 3N). 1.1352 -Me -Me - 6-F 3-C1 (£) - 4-'H NMR (400 MHz, CDC13) δ (C=sour CH=CH-fluoro ppm 7.45 (dd, 1 H) 7.29 - 7.37 g phenyl (m, 2 Η) 6.96 - 7.07 (m, 3 Η) 6.92 (d, 1 Η) 6.59 (d, 1 Η) 3.75 (s, 3 Η) 2.66 (septet, 1 Η) 2.26 (s, 3 Η) 1.09 (dd , 6 Η). 1.1357 -Me -Me - 6-F 3-C1 (£) - 4- (tri- 'H NMR (400 MHz, (C=O)'P CH=CH-fluoro-chloroform) δ = 7.43 (dd, 1 =

- 85 040613

G methoxy)phenyl 5.1, 8.9 Hz, 1H), 7.40 - 7.34 (m, 2H), 7.18 - 7.11 (t, J = 7.9 Hz, 2H), 7.03 (t , J = 8.9 Hz, 1H), 6.98 (d, J = 16.5 Hz, 1H), 6.64 (d, J = 16.5 Hz, 1H), 3.71 (s, ZH ), 2.64 (septet, J = 7.0 Hz, 1Н), 2.22 (s, ZN), 1.09 (d, J = 7.0 Hz, ZN), 1.07 (d, J = 7.0 Hz, ZN) 1.1363 -Me -Me (C=our r 6-F 3-C1 (E)- CH=CH- 4-cyclopropylphenyl 'H NMR (400 MHz, chloroform) δ = 7.41 (dd, J = 5.1, 8.9 Hz, 1H), 7.26 - 7.22 (m, 2H), 7.02 - 6, 98 (m, 2H), 6.99 (t, J = 8.9 Hz, 1H), 6.93 (d, J = 16.5 Hz, 1H), 6.59 (d, J = 16.5 Hz, 1H), 3.71 (s, 3H), 2.62 (septet, J = 7.0 Hz, 1H), 2.19 (s, 3H), 1.87 (tt, J = 5.0 , 8.4 Hz, 1H), 1.07 (d, J = 7.0 Hz, ZN), 1.06 (d, J = 7.0 Hz, 1H), 0.99 - 0.93 (m , J = 2.0, 8.4 Hz, 2H), 0.73 - 0.64 (m, 2H) 1.1367 -Me -Me (C=O/P r 6-F 3-C1 ®- CH=CH- 4- (tert-butoxy)phenyl 'H NMR (400 MHz, chloroform) δ = 7.41 (dd, J = 5.0, 8.6 Hz, 1H), 7.26 - 7.23 (m, 2H), 6.99 (t, J = 8.6 Hz, 1H), 6.94 - 6.90 (m, 1H), 6.91 (d, J = 16.5 Hz, 1H), 6.60 (d, J = 16.5 Hz, 1H), 3.71 (s, 3H), 2.63 (septet, J = 7.0 Hz, 1H), 2.22 (s, 3H), 1.35 (s, 9H), 1, 08 (d, J = 7.0 Hz, ZN), 1.06 (d, J = 7.0 Hz, 1H) 1.1369 -Me -Me (C=O/P r 6-F 3-C1 (E)- CH=CH- 2- cyanophenyl 'H NMR (400 MHz, chloroform) δ = 7.70 (d, J = 8.1 Hz, 1H), 7.61 - 7.53 (m, 2H), 7.46 (dd, J = 5, 1, 8.9 Hz, 1H), 7.34 (dt, J = 1.0, 7.6 Hz,

- 86 040613

1H), 7.24 (d, J = 16.5 Hz, 1H), 7.10 - 6.97 (m, 2H), 3.76 (s, 3H), 2.65 (septet, J = 7 .0 Hz, 1H), 2.26 (s, 3H), 1.08 (dd, J = 3.0, 7.0 Hz, 6H).

1.1370 -Me -Me (ooyp r 6-F 3-C1 (E)- CH=CH- 3- cyanophenyl Ή NMR (400 MHz, chloroform) δ = 7.63 - 7.55 (m, 2H), 7.55 - 7.50 (m, 1H), 7.48 - 7.38 (m, 2H), 7 ,12 7.00 (m, 2H), 6.65 (d, J = 16.5 Hz, 1H), 3.70 (s, 3H), 2.65 (septet, J = 7.0 Hz, 1H ), 2.24 (s, 3H), 1.09 (dd, J = 7.0, 12.5 Hz, 6H). 1.1371 -Me -Me (ooyp r 6-F 3-C1 (E)- CH=CH- 3-trifluoro- methylphenyl 'H NMR (400 MHz, chloroform) δ = 7.57 (s, 1H), 7.54 - 7.48 (m, 2H), 7.47 7.39 (m, 2H), 7.10 - 7 .00 (m, 2H), 6.68 (d, J = 16.5 Hz, 1H), 3.72 (s, 3H), 2.65 (septet, J = 7.0 Hz, 1H), 2 .24 (s, 3H), 1.09 (t, J = 7.4 Hz, 6H). 1.1372 -Me -Me (C=O/P r 6-F 3-C1 (E)- CH=CH- 0- tolil 'H NMR (400 MHz, chloroform) δ = 7.51 - 7.39 (m, 2H), 7.22 - 7.13 (m, 2H), 7.13 - 7.08 (m, 1H), 7.01 (t, J = 8.7 Hz, 1H), 6.94 - 6.78 (m, 2H), 3.75 (s, 3H), 2.61 (septet, J = 7.0 Hz , 1H), 2.22 (s, 3H), 2.12 (s, 3H), 1.06 (dd, J = 0.6, 7.0 Hz, 6H). 1.1373 -Me -Me (OO/P r 6-F 3-C1 (E)- CH=CH- m- tolil 'H NMR (400 MHz, chloroform) δ = 7.42 (dd, J = 5.1, 8.9 Hz, 1H), 7.23 - 7.10

(m, 3H), 7.07 (d, J = 7.3 Hz, 1H), 7.04 - 6.94 (m, 2H), 6.59 (d, J = 16.5 Hz, 1H) , 3.73 (s, 3H), 2.63 (quintet, J = 7.0 Hz, 1H), 2.34 (s, 3H), 2.21 (s,

- 87 040613

ZN), 1.08 (dd, J = 2.8, 7.0 Hz,

6H). 1.1383 -Me -Me - (C=O)P G 6-F 3-C1 (£) - Thio- 'H NMR (400 MHz, CH=CH-phen-3-chloroform) δ=7.42 (dd, J=yl 5.1, 8.8 Hz, 1H), 7.30 - 7.21 (m, 2H + CHC13 peak), 7.15 (dd, J = 1.2, 2.8 Hz, 1H), 7.00 (t, J = 8.7 Hz, 1H), 6.89 - 6 .80 (t, 1H), 6.69 - 6.61 (t, 1H), 3.74 (s, ZH), 2.62 (septet, J = 7.0 Hz, 1H), 2.23 ( s, ZN), 1.06 (dd, J = 5.5, 7.0 Hz, 6H). 1.1387 -Me -Me - (C=O)P G 6-F 3-C1 (E) - 5-me- 'H NMR (400 MHz, CH=CH-tyl-3-chloroform) δ ppm 8.32 (s, 2 pyri- Η), 7.52 (s, 1 Η), 7.44 (dd, dyl >8.93, 5.14 Hz , 1 H), 7.10 - 6.99 (m, 2 Η), 6.63 (d, >16.51 Hz, 1 Η), 3.71 (s, 3 Η), 2.65 (quintet, J=7.00 Hz, 1 Η), 2.34 (s, 3 Η) 2.23 (s, 3 Η) 1.09 (t, >7.15 Hz, 6 Η) 1.1391 -Me -Me - (C=O)P G 6-F 3-C1 (E) - 6-chloro-'H NMR (400 MHz, CH=CH-3-chloroform) δ ppm 8.28 (d, pyri->2.45 Hz, 1 H) 7.68 (dd, dil >8.31, 2.45 Hz, 1 H) 7.45 (dd, >8.86, 5.07 Hz, 1 H) 7.26 - 7.29 (m, 1 H) 7.00 7.10 (m, 2H) 6.64 (d, >16.63 Hz, 1 H) 3.70 (s, 3 H) 2.54 2.74 (m, 1 H) 2.23 (s, 3 H) 1.08 (dd, >11.80, 7.03 Hz , 6H) 1.1392 -Me -Me - (C=O)P G 6-F 3-C1 (E) - 2-tri-'H NMR (400 MHz, CH=CH-fluoro-chloroform) δ = 8.57 (dd, J = methyl- 1.2, 4.7 Hz, 1H), 8.05 (dd, J = 3-pi- 1.2, 7.9 Hz, 1H), 7.50 (dd, J= ridyl 4.7, 7.9 Hz, 1H), 7.46 (dd, J = 5.1, 8.9 Hz, 1H), 7.11 (d, J = 16.2 Hz, 1H), 7.07 (t, J = 8.9

- 88 040613

Hz, 1H), 7.03 (qd, J = 2.0, 16.2 Hz, 1H), 3.74 (s, 3H), 2.63 (septet, J = 7.0 Hz, 1H), 2.24 (s, 3H), 1.07 (d, J = 7.0 Hz, 6H)

1.1393 -Me -me- (C=our r 6-F 3-C1 (£)CH=CH- 3,5-difluorophenyl Ή NMR (400 MHz, chloroform) δ = 7.44 (dd, J = 5.1, 8.9 Hz, 1H), 7.04 (t, J = 1.1394 -Me -Me 6-F 3-C1 (£) - 4-me- 8.9 Hz, 1H), 7.01 (d, J = 16.4 Hz, 1H), 6.89 - 6.83 (m, 2H), 6.69 (tt, J = 2.3, 8 .8 Hz, 1H), 6.58 (d, J = 16.4 Hz, 1H), 3.72 (s, 3H), 2.64 (septet, J = 7.0 Hz, 1H), 2, 23 (s, 3H), 1.10 (d, J = 7.0 Hz, VN), 1.07 (d, J = 7.0 Hz, VN) 'H NMR (400 MHz, 1.1447 -Me -Me (C=our r H 6-F 3-C1 CH=CH- -c=c- til-2pyriDIL phenyl chloroform) δ ppm 8.41 (d, 1=5.01 Hz, 1 H) 7.50 (d, 1=16.26 Hz, 1 H) 7.43 (dd, 1=8.86, 5, 07 Hz, 1 Η) 6.93 7.07 (m, 3 Η) 6.68 (d, 1=16.26 Hz, 1 Η) 3.74 (s, 3 Η) 2.62 (dt, 1 =13.94, 6.97 Hz, 1 Η) 2.32 (s, 3 Η) 2.21 (s, 3 Η) 1.06 (dd, 1=6.97, 5.62 Hz, 6 Η ) 'H NMR (400 MHz, 1.1454 -Me -Me H 6-F 3-C1 -c=c- 4- chloroform) δ ppm 7.35 (dd, 1=8.00, 5.00 Hz, 1 H), 7.33 7.27 (m, 5H), 6.98 (t, 1=8.60 Hz, 1H), 3.71 - 3.63 (m, ZN), 2.32 - 2.26 (m, ZN) 'H NMR (400 MHz, 1.1457 -Me -Me H 6-F 3-C1 -c=c- fluorophenyl 2-three- chloroform) δ ppm 7.47 (dd, 1=8.93, 5.01 Hz, 1 H), 7/357/28 (m, 2H), 7.10 (t, 1=8.50 Hz, 1H ), 7.05 - 6.98 (m, 2H), 3.73 (s, 3H), 2.34 (s, 3H) 'H NMR (400 MHz,

- 89 040613 fluoro-chloroform) δ ppm 7.61 methyl- 7.37 (m, 4 Η), 7.23 (dd, phenyl J=8.00, 5.00 Hz, 1 Η), 6.88 ( br t, >8.44Hz, 1H), 3.58(s, 3H), 2.22(s, 3H)

1.1458 -Me -Me H 6-F 3-C1 -c=c- TI- TO lil Ή NMR (400 MHz, chloroform) δ ppm 7.36 (dd, >9.00, 5.00 Hz, 1 Η), 7.22 7.16 (m, 2H), 7.14 - 7.08 ( m, 2H), 6.98 (t, >8.50 Hz, 1 Η), 3.68 (s, ZN), 2.35 (s, ZN), 2.29 (s, ZN) 1.1556 -Me -Me (C=O/P r 6-F 3-C1 -c=c- 4- fluorophenyl 'H NMR (400 MHz, CDC13) δ ppm 7.46 (dd, 1 Η) 7.31 -7.38 (m, 2 Η) 7.08 (t, 1 Η) 6.99 7.06 (m , 2 Η) 3.83 (s, 3 Η) 2.61 (septet, 1 Η) 2.28 (s, 3 Η) 1.04 (dd, 6 Η). 1.1560 -Me -Me (C=our r 6-F 3-C1 -c=c- P- tolil 'Η NMR (400 MHz, chloroform) δ ppm 7.44 (dd, >9.00, 5.00 Hz, 1 Η), 7.26 7.20 (m, 2H), 7.16 -7.09 (m, 2H), 7.06 (t, >8.50 Hz, 1 H), 3.82 (s, £H), 2.60 (septet, >7.00 Hz, 1H), 2.35 (s, ZN), 2.27 (s, ZN), 1.04 (d, >7.00 Hz, 3 N), 1.03 (d, >7.00 Hz, 3 N) 1.1651 -Me -Me (C=O)M e 6-F 3-C1 -CH ₂ -CH ₂ - P- tolil 'H NMR (400 MHz, chloroform) δ ppm 7.44 (dd, >8.86, 5.20 Hz, 1 Η), 7.11 6.94 (m, 5H), 3.84 (s, £ H), 2.89-2.69 (m, 4H), 2.32 (s, 3H), 2.06 (s, 3H) 1.1652 -Me -Me (C=O) ^From Bu 6-F 3-C1 -CH ₂ -CH ₂ - P- tolil 'H NMR (400 MHz, chloroform) δ ppm 7.42 (dd, >8.80, 5.14 Hz, 1 H), 7.10 -

7.04 (m, 2H), 7.04 - 6.94 (m,

3H), 3.78 (s, 3H), 2.88 (br d,

- 90 040613

1=7.83 Hz, 2 Η), 2.69 (td, 1=12.72, 11.37 Hz, 2 Η), 2.36 (s, 3 Η), 2.31 (s, 3 Η ), 1.10 (s, 9 Η)

1.1653 -Me -Me (C=O)O -me 6-F 3-C1 -CH ₂ -CH ₂ - TI- TO lil Ή NMR (400 MHz, chloroform) δ ppm 7.44 (dd, 1=8.86, 5.20 Hz, 1 Η), 7.12 6.94 (m, 5Η), 3.83 (s, 3N ), 3.76 (s, 3H), 2.88 - 2.70 (m, 4H), 2.38 - 2.24 (m, 6H) 1.1654 -Me -Me (C=O)tB u 6-F 3-C1 -CH ₂ -CH ₂ - P- TOLIL 'H NMR (400 MHz, chloroform) δ ppm 7.42 (dd, 1=8.80, 5.14 Hz, 1 H), 7.11 6.94 (m, 5H), 3.85 (s, 3H), 2.90 - 2.68 (m, 4H), 2.32 (s, 3H), 2.24 (s, 3H), 1.03 (s, 9H) 1.1655 -Me -Me (C=O)Ph 6-F 3-C1 -CH ₂ -CH ₂ - P- TOLIL 'H NMR (400 MHz, chloroform) δ ppm 7.90 (dd, 1=8.38, 1.28 Hz, 2 Η), 7.65 -

7.57 (m, 1H), 7.48 - 7.39 (m, 2H), 7.32 (dd, 1=8.80, 5.14 Hz, 1 H), 7.13 - 7.02 (m, 4H), 6.91 (t, 1=8.68 Hz, 1 H), 3.87 (s, 3H), 2.92 - 2.70 (m, 4H), 2.28 - 2 .23 (m, 6H)

1.1656 -Me -me- 6-F 3-C1 -CH ₂ -CH ₂ - P- 'H NMR (400 MHz, (C=O)4- tolil chloroform) δ ppm 7.46 (dd, sea- 1=8.86, 5.20 Hz, 1 H), 7.11 - foLINO 6.96 (m, 5H), 3.85 (s, 3H), 3.59-3.20 (m, 8H), 2.96-2.67 (m, 4H), 2.40-2.22 (m, 6H)

The numbering system used to describe the X and Y positions is shown for clarity only.

biological examples.

IN 1. Post-emergence efficiency - test 1.

Seeds of a number of tested species were sown in standard soil in pots: Solarium nigrum (SOLNI), Amaranthus retoflexus (AMARE), Setaria faberi (SETFA), Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE), Lolium perenne (LOLPE). After cultivation for 8 days (post-emergence) under controlled conditions in a greenhouse (at 24/16°C, day/night; 14-hour photoperiod; humidity 65%), the plants were sprayed with an aqueous spray solution prepared from a formulation based on technical active ingredient in an acetone/water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5). The compounds were applied at the rate of 1000 g/ha. The test plants were then grown in a greenhouse under controlled greenhouse conditions (at 24/16°C, day/night; 14 hour photoperiod; 65% humidity) and watered twice a day. After 13 days, the test assessed the proportion of damage that was caused to the plant. Biological activity values were determined on a five-point scale (5=80-100%; 4=60-79%; 3=40-59%; 2=20-39%; 1=0-19%). The absence of a value in the table indicates that the compound was not tested against this species.

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Table 3

Control of certain weed species with compounds of formula (I) after post-emergence application

Compound AMARE SOLNI SETFA lolpe ECHCG IPOHE 1.0001 5 5 5 5 5 5 1.0002 4 5 3 4 4 5 1.0012 5 5 5 5 5 5 1.0018 5 5 5 5 5 5 1.0024 5 5 5 5 5 5 1.0042 5 5 5 5 5 5 1.0048 5 5 5 5 5 5 1.0054 5 5 5 5 5 5 1.0060 5 5 5 5 5 5 1.0066 5 5 5 4 5 5 1.0089 5 5 5 5 5 5 1.0095 5 5 5 5 5 1.0125 5 5 5 5 5 5 1.0149 5 5 5 5 5 5

AT 2. Post-emergence efficiency - test 2.

Seeds of a number of tested species were sown in standard soil in pots: Solarium nigrum (SOLNI), Amaranthus retoflexus (AMARE), Setaria faberi (SETFA), Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE), Lolium perenne (LOLPE). After cultivation for 8 days (post-emergence) under controlled conditions in a greenhouse (at 24/16°C, day/night; 14-hour photoperiod; humidity 65%), the plants were sprayed with an aqueous spray solution prepared from a formulation based on technical active ingredient in an acetone/water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5). The compounds were applied at the rate of 250 g/ha. The test plants were then grown in a greenhouse under controlled greenhouse conditions (at 24/16°C, day/night; 14 hour photoperiod; 65% humidity) and watered twice a day. After 13 days, the test assessed the proportion of damage that was caused to the plant. Biological activity values were determined on a five-point scale (5=80-100%; 4=60-79%; 3=40-59%; 2=20-39%; 1=0-19%). The absence of a value in the table indicates that the compound was not tested against this species.

Table 4

Control of certain weed species with compounds of formula (I) after post-emergence application

Compound AMARE SOLNI SETFA lolpe ECHCG IPOHE 1.0001 4 5 5 5 5 5 1.0002 1 5 1 1 0 5 1.0012 4 5 5 5 5 5 1.0018 5 5 5 5 5 5 1.0024 5 5 5 5 5 5 1.0042 5 5 5 5 5 5 1.0048 4 5 5 5 5 5 1.0054 4 5 5 4 4 3 1.0060 4 5 5 5 5 5 1.0066 5 5 4 2 3 5 1.0072 5 5 5 5 5 5 1.0089 4 5 5 5 5 5 1.0101 5 5 4 4 4 5 1.0119 3 5 4 4 3 4 1.0095 5 5 5 5 5 1.0143 5 5 2 2 2 5 1.0125 3 5 5 5 5 5 1.0327 5 5 5 5 5 5 1.0333 5 5 5 5 5 5 1.0339 1 5 5 1 3 5

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1.0345 5 5 5 5 5 5 1.0351 5 5 5 5 5 5 1.0363 4 5 5 5 5 4 1.0369 4 5 4 4 4 4 1.0375 5 5 5 5 5 5 1.0387 5 5 5 5 5 5 1.0417 5 5 5 5 2 5 1.0429 5 5 5 5 5 5 1.0441 5 5 5 5 4 5 1.0597 4 5 4 4 2 5 1.0603 4 5 4 5 4 5 1.0609 5 5 2 4 3 5 1.0615 4 5 5 5 4 5 1.0621 5 5 4 4 4 5 1.0627 5 5 5 5 5 5 1.0633 5 5 5 5 5 5 1.0639 4 5 2 2 2 1 1.0645 5 5 5 5 5 5 1.0651 4 5 4 4 4 5 1.0657 5 5 5 5 1 5 1.0663 5 5 5 4 2 5 1.0669 4 5 2 2 1 5 1.0675 5 5 5 4 2 5 1.0681 3 5 2 3 3 5 1.0687 4 5 5 5 5 5 1.0693 4 - 4 4 4 4 1.0789 5 5 5 5 5 5 1.0885 5 5 5 5 4 5 1.0891 5 5 4 4 4 4 1.0897 4 5 4 4 4 5 1.0149 4 5 5 5 5 5 1.0969 5 5 4 4 4 4

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1.0999 5 5 5 5 4 5 1.1005 4 5 4 4 3 3 1.1257 4 5 5 5 5 4 1.1258 3 5 5 5 5 5 1.1259 1 5 1 2 2 2 1.1265 2 5 1 2 2 3 1.1267 4 5 0 1 1 3 1.1269 3 4 0 1 0 4 1.1270 2 4 0 0 0 0 1.1271 0 5 1 1 0 4 1.1348 2 5 1 3 3 4 1.1351 3 5 4 4 4 4 1.1352 2 4 2 2 3 4 1.1357 2 5 3 2 5 3 1.1363 1 5 0 1 1 2 1.1367 1 3 0 0 0 3 1.1369 4 4 0 1 1 4 1.1370 2 3 0 1 1 3 1.1372 1 - 1 2 2 5 1.1383 2 5 0 0 0 4 1.1387 0 0 0 0 0 2 1.1454 4 5 4 5 5 5 1.1457 4 5 1 1 1 4 1.1556 3 5 4 5 5 5 1.1651 4 5 5 5 5 4 1.1652 3 3 3 1 0 1 1.1653 4 5 5 5 5 5 1.1654 4 5 5 3 5 5 1.1655 3 5 2 1 3 1 1.1656 3 5 2 1 2 4

VZ. Post-emergence efficiency - test 3.

Seeds of a number of tested species (see Table B1) were sown in standard soil in pots. After cultivation for 12 days (post-emergence) under controlled conditions in a greenhouse (at 24/18°C or 20/16°C, day/night; 16-hour photoperiod; 65% humidity), the plants were sprayed with an aqueous spray solution obtained from a formulation based on a technical active ingredient dissolved in IF50 (for the formulation, see Table B2), and an adjuvant (Genapol XO80) was added to the spray solution at a rate of 0.2% v/v.

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Table B1

Plant species tested and abbreviations used

Plant species for cold climates: Abbreviation Hordeum vulgare HORVW Triticum aestivum TRZAW Brassica napus BRSNN beta vulgaris BEAVA Alopecurus myosuroides ALOMY Avena fatua AVEFA Bromus tectorum BROTE Lolium perenne lolpe Poa annua POAAN Chenopodium album CH AL Galium aparine GALAP Kochia scoparia KSHSC Polygonum convolvulus POLCO Sinapis arvensis SINAR Stellaria media STEM Veronica persica VERPE Types for warm climate: Orysa sativa ORYSA Zea mays ZEAMX Glycinemax GLXMA Brachiaria plantaginea BRAPL Digitaria sanguinalis DIGSA Echinochloa crus galli ECHCG Eleisine indica ELEIN Panicum miliaceum PANMI Setaria faberi SETFA Sorghum bicolour SORVU Abutilon theophrasti ABUTH Amaranthus retroflexus AMARE Bidens pilosa VSHR1 Euphorbia hetrophylla EPHHL Ipomoea hederacea IPOHE Sida spinosa SIDSP Xanthium strumarium XANST Cyperus esculentus CYPES

Table B2

Chemical composition of IF50

Component Chemical name Function CAS registration number Quantity (% w/w) EmulsogenEL360 ^1M Castor oil ethoxylate Emulsifier 61791-12-6 11.12 A-methylpyrrolidone 1-methyl-2-pyrrolidone Solvent 872-50-4 44.44 glycol ether Dowanol DPM Dipropylene glycol monomethyl ether Solvent 34590-94-8 44.44

After application of the agents, the test plants were grown in a greenhouse under controlled conditions (described above) and watered twice a day. Herbicidal activity was assessed on a scale of 0-100 15 days after application. The results, where 0=no damage to the test plant and 100=total test plants destroyed, are shown in Table 1 below. 5-8. The absence of a value in the table indicates that the compound was not tested against this species.

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Table 5

Control of some species of heat-loving plants with compounds _________ of formula (I) after post-emergence application _____________

Connection ID Application rate (g/ha) Types of heat-loving plants ZEAMX GLXMA ORYSA SETFA PANMI SORVU DIGSA ECHCG BRAPL ELEIN 1.0001 500 20 90 0 90 100 20 70 90 80 thirty 250 10 80 0 90 90 10 70 80 70 125 10 80 0 80 80 10 70 80 50 60 10 80 0 80 80 0 80 50 thirty 0 60 0 70 70 0 70 thirty 15 0 0 40 50 0 50 70 50 thirty 1.0012 500 100 100 thirty 100 100 90 70 100 100 80 250 70 90 10 80 100 80 50 90 90 80 125 50 90 0 70 80 70 20 90 80 60 60 50 90 0 40 thirty 70 20 80 80 60 thirty 10 80 0 40 20 thirty 10 80 60 50 15 0 70 0 0 0 0 0 60 20 0 1.0018 500 70 90 40 90 100 100 70 90 100 80 250 thirty 90 20 90 100 90 70 90 70 70 125 20 70 10 80 80 80 40 90 80 70 60 20 70 0 70 60 60 20 90 70 thirty 20 40 0 70 50 20 20 80 60 20 15 0 20 0 0 0 0 0 20 0 0 1.0024 500 90 100 50 100 100 100 90 100 90 90 250 70 100 20 90 100 90 80 100 90 80 125 60 90 0 90 90 90 70 90 90 80 60 20 90 0 90 80 80 70 90 90 70 thirty 10 80 0 80 60 70 60 90 80 70 15 0 60 0 40 10 0 0 80 80 0 1.0042 500 100 100 40 100 100 100 90 100 90 80 250 70 100 20 90 90 90 90 90 70 80 125 40 90 0 90 90 80 80 90 70 60 60 20 90 0 80 80 70 40 80 70 40 thirty 10 80 0 70 70 10 20 80 60 40 15 0 70 0 20 0 0 0 70 thirty 0 1.0048 500 100 100 50 80 90 90 thirty 100 90 90 250 90 100 20 60 80 90 40 90 90 90 125 thirty 10 60 60 90 10 90 80 60 thirty 80 0 thirty 50 70 0 80 70 thirty 20 70 0 20 20 60 0 80 90 0 15 0 0 0 0 0 0 80 80 0 1.0066 500 60 90 10 10 50 10 10 80 10 0 250 40 90 0 0 20 10 0 60 0 0 125 thirty 80 0 0 0 10 0 60 0 0 60 20 80 0 0 0 0 0 40 0 0 thirty 10 40 0 0 0 0 0 thirty 0 0 15 10 40 0 0 0 0 0 10 0 0 1.0072 500 20 40 0 80 70 0 20 70 40 0 250 0 40 0 60 20 0 10 60 20 0 125 0 thirty 0 thirty 10 0 60 10 0 60 0 thirty 0 20 0 0 0 50 10 0 thirty 0 20 0 0 0 0 40 20 0 15 0 10 0 0 0 0 0 0 0 1.0095 500 thirty 50 thirty 60 70 60 60 80 80 thirty 250 10 50 10 40 40 50 thirty 80 70 125 0 40 0 40 10 40 70 70 60 0 thirty 0 20 20 50 60 60 20 thirty 0 20 0 10 10 20 10 50 50 15 0 10 0 0 0 0 thirty 10 1.0101 500 10 90 20 90 70 70 70 50 80 20 250 0 80 0 50 70 0 10 60 60 125 0 40 0 50 0 0 0 40 70 10 60 0 50 0 thirty thirty 0 0 60 0 thirty 0 thirty 0 20 60 0 0 40 60 15 0 thirty 0 0 0 0 thirty 40

- 96 040613

1.0125 500 70 90 0 100 80 90 70 100 80 80 250 40 90 0 20 70 80 thirty 90 70 80 125 20 0 20 50 70 10 80 80 70 60 thirty 70 0 20 50 50 0 80 80 70 thirty 20 70 0 10 thirty 50 0 80 40 15 0 40 0 0 20 0 0 70 80 40 1.0149 500 0 40 10 20 40 0 10 80 10 0 250 0 thirty 10 20 40 0 10 70 10 0 125 0 thirty 0 10 10 0 0 70 0 0 60 0 20 0 0 0 0 0 70 0 0 thirty 0 20 0 0 0 0 0 70 0 0 15 0 10 0 0 0 0 0 60 0 0 1.0327 500 70 90 0 80 90 80 thirty 90 90 40 250 10 90 0 60 70 40 70 80 thirty 125 0 80 0 thirty 10 10 50 20 60 0 60 0 20 10 10 thirty 40 thirty 0 40 0 0 80 20 0 20 thirty 15 0 20 0 0 0 0 10 0 1.0333 500 90 90 0 90 100 90 90 90 90 70 250 70 90 0 80 90 80 50 80 80 125 40 90 0 80 100 70 40 80 80 60 10 80 0 60 70 10 60 70 10 thirty 0 80 0 thirty 80 20 0 60 70 15 0 70 0 0 0 10 0 thirty 70 0 1.0345 500 20 60 thirty 50 10 20 0 thirty 0 thirty 250 0 thirty 20 thirty 20 0 0 20 125 0 40 0 0 0 10 0 20 0 20 60 0 40 0 0 0 0 20 0 20 thirty 0 20 0 0 0 0 0 0 0 0 15 0 10 0 0 0 0 0 0 0 1.0351 500 20 80 10 80 100 50 0 70 60 20 250 10 70 10 70 90 0 40 50 10 125 0 60 0 60 50 0 0 50 60 60 0 40 0 40 60 0 0 50 60 thirty 0 20 0 thirty 100 0 0 40 0 15 0 10 0 0 10 0 0 0 0 1.0387 500 60 90 0 100 100 90 100 100 100 50 250 40 90 0 90 80 70 80 90 100 50 125 20 90 0 90 70 60 40 90 100 40 60 10 90 0 90 70 40 90 thirty thirty 0 90 0 80 60 thirty thirty 80 90 20 15 0 90 0 80 60 10 0 60 90 10 1.0417 500 thirty 40 0 0 0 0 0 0 10 10 250 0 20 0 0 0 0 0 0 0 125 0 10 0 0 0 0 0 0 0 10

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60 0 10 0 0 0 0 0 0 0 10 thirty 0 10 0 0 0 0 0 0 0 15 0 10 0 0 0 0 0 0 0 500 20 60 thirty 90 70 0 0 60 70 thirty 250 0 50 20 60 80 0 0 50 thirty 20 125 0 40 0 50 20 0 0 thirty 10 60 0 20 0 20 0 0 0 20 0 thirty 0 10 0 thirty 0 0 0 10 0 10 15 0 10 0 10 0 0 0 0 0 500 50 50 thirty 80 60 20 thirty 80 90 0 250 10 40 20 70 50 10 thirty 70 80 0 125 0 thirty 0 50 40 0 thirty 60 70 0 60 20 20 0 40 thirty 0 20 60 60 0 thirty 0 10 0 thirty 20 0 20 60 0 15 0 10 0 10 10 0 0 10 0 500 40 100 thirty 90 70 80 90 100 100 50 250 thirty 90 20 80 60 70 80 90 100 50 125 20 80 10 70 60 70 80 80 90 60 10 80 10 70 50 50 50 80 90 thirty thirty 0 70 0 10 thirty 20 80 80 20 15 0 40 0 20 0 0 10 80 0 500 10 thirty 0 40 10 thirty 0 40 thirty 10 250 0 10 0 thirty 60 0 0 thirty 0 125 0 10 0 20 80 0 40 0 60 0 10 0 60 10 0 0 0 0 thirty 0 10 0 50 0 0 0 0 15 0 10 0 20 0 0 0 40 0

Table 6

Control of some species of heat-loving plants with compounds of formula (I) after post-emergence application

Connection ID Application rate (g/ha) Types of heat-loving plants ZEAMX GLXMA ORYSA EPHHL SIDSP ABUTH XANST IPOHE BIDPI AMARE 1.0001 500 100 70 100 90 90 90 80 100 70 100 250 90 60 90 90 80 50 70 90 60 90 125 90 60 90 90 80 40 70 90 60 90 60 80 60 90 90 80 40 70 80 60 90 thirty thirty 60 90 90 80 thirty 70 thirty 60 90 15 20 40 80 90 80 20 60 20 40 80 1.0012 500 100 90 100 100 100 100 100 100 90 100 250 100 90 90 90 100 100 100 100 90 90

- 98 040613

125 90 90 90 90 100 70 90 90 90 90 60 90 80 90 90 100 70 90 90 80 90 thirty 70 80 80 80 70 80 70 80 80 15 50 80 60 70 70 60 50 80 60 500 100 100 100 100 100 90 100 100 100 100 250 100 90 90 100 100 90 100 100 90 90 125 90 90 90 100 80 100 90 90 90 60 80 80 50 90 90 70 90 80 80 50 thirty 70 80 50 90 60 90 70 80 50 15 60 40 20 70 50 90 60 40 20 500 100 100 100 100 100 90 100 100 100 100 250 100 100 100 100 100 80 100 100 100 100 125 100 100 90 100 70 100 100 100 60 90 100 100 100 70 100 90 100 100 thirty 90 90 90 100 70 100 90 90 90 15 80 90 80 80 100 70 80 90 80 500 100 100 100 100 100 90 100 100 100 100 250 100 100 100 100 80 100 100 100 100 125 90 100 100 80 100 80 100 90 100 100 60 90 90 100 80 100 80 90 90 90 100 thirty 90 90 90 100 80 90 90 90 90 15 70 80 90 80 80 70 80 90 500 100 100 100 100 100 100 100 100 100 100 250 100 100 100 90 100 80 100 100 100 100 125 100 100 100 90 100 80 100 100 100 100 60 100 90 100 80 100 70 90 100 90 100 thirty 100 80 90 90 100 60 80 100 80 90 15 80 70 100 70 80 80 70 500 70 90 90 80 90 70 80 70 90 90 250 70 90 80 80 90 50 80 70 90 80 125 60 80 80 80 80 50 80 60 80 80 60 60 80 80 70 80 40 70 60 80 80 thirty thirty 60 70 70 80 40 80 thirty 60 70 15 thirty 60 60 70 60 40 80 thirty 60 60 500 70 50 90 90 60 80 70 50 90 250 70 80 90 10 80 70 80 125 60 20 80 80 10 80 60 20 80 60 80 70 10 70 80 thirty 20 10 70 60 0 50 20 10 70 15 10 70 thirty 0 40 10 70 500 90 70 80 70 thirty 80 90 70 80 250 60 40 thirty 0 80 60 40 125 50 thirty 60 thirty 0 80 50 thirty 60 60 50 20 60 40 0 80 50 20 60 thirty 40 40 20 0 70 40 40

- 99 040613

15 40 20 10 0 70 40 20 500 70 70 90 90 thirty 80 70 70 90 250 50 60 80 80 0 80 50 60 80 125 40 80 60 0 80 40 80 60 80 80 0 80 80 thirty 50 thirty 70 90 0 80 50 thirty 70 15 20 thirty 70 80 0 80 20 thirty 70 500 100 100 100 100 100 100 100 100 100 100 250 100 90 100 90 100 80 100 100 90 100 125 100 90 90 90 100 70 100 100 90 90 60 100 80 90 90 100 70 90 100 80 90 thirty 90 90 90 100 60 90 90 90 15 90 80 90 60 80 90 80 500 80 50 80 80 80 60 90 80 50 80 250 70 50 70 70 70 50 80 70 50 70 125 70 40 70 70 70 40 80 70 40 70 60 60 50 70 60 50 40 80 60 50 70 thirty 40 50 70 60 thirty thirty 70 40 50 70 15 40 40 70 60 thirty thirty 50 40 40 70 500 80 90 90 90 70 80 80 90 90 250 80 20 80 90 40 70 80 20 80 125 60 thirty 80 90 20 50 60 thirty 80 60 60 20 80 90 10 50 60 20 80 thirty 40 40 thirty 0 40 40 40 15 20 10 20 20 0 thirty 20 10 20 500 100 80 100 90 60 90 100 80 100 250 80 80 90 90 40 90 80 80 90 125 70 80 90 90 thirty 90 70 80 90 60 60 thirty 80 90 0 80 60 thirty 80 thirty 50 80 90 80 50 80 15 50 70 90 80 50 70 500 80 40 80 80 thirty 80 80 40 80 250 70 70 80 80 70 70 125 60 60 70 80 60 60 60 50 40 60 60 0 80 50 40 60 thirty thirty 50 40 0 80 thirty 50 15 thirty 20 20 0 80 thirty 20 500 80 80 90 90 thirty 80 80 80 90 250 60 20 80 90 20 70 60 20 80 125 60 20 80 90 10 60 60 20 80 60 70 60 80 0 60 70 60 thirty 50 60 90 0 50 50 60 15 40 10 80 0 50 40 10 500 100 90 90 100 50 90 100 90 90 250 90 80 90 90 40 90 90 80 90

- 100 040613

125 90 70 90 90 thirty 90 90 70 90 60 80 60 90 90 20 90 80 60 90 thirty 70 50 80 90 10 80 70 50 80 15 50 80 90 10 80 50 80 500 60 60 60 80 0 70 60 60 60 250 60 0 70 70 0 60 60 0 70 125 40 0 60 60 0 50 40 0 60 60 thirty 50 10 0 40 thirty 50 thirty thirty 40 0 0 50 thirty 40 15 20 0 0 0 thirty 20 0 500 70 50 90 90 40 80 70 50 90 250 40 60 80 90 thirty 80 40 60 80 125 thirty 80 90 10 70 thirty 80 60 20 70 90 0 50 20 70 thirty 10 0 70 90 0 50 10 0 70 15 0 0 60 90 0 40 0 0 60 500 80 60 90 100 60 70 80 60 90 250 70 50 80 90 40 60 70 50 80 125 50 40 80 90 thirty 40 50 40 80 60 40 20 80 90 20 40 20 80 thirty thirty 20 70 80 10 40 thirty 20 70 15 20 50 60 10 thirty 20 50 500 90 90 90 100 70 90 90 90 90 250 80 90 90 100 50 80 80 90 90 125 70 80 80 90 80 70 80 80 60 60 80 70 90 40 80 60 80 70 thirty 40 60 70 90 20 60 40 60 70 15 40 50 60 80 10 60 40 50 60 500 60 thirty 80 90 90 70 60 thirty 80 250 60 20 70 80 40 80 60 20 70 125 40 70 thirty 60 40 70 60 40 70 70 20 60 40 70 thirty thirty 10 70 70 10 50 thirty 10 70 15 20 70 50 10 40 20 70

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Table 7

Control of some species of cold-resistant plants with compounds of formula (I) after post-emergence application

Connection ID Application rate (g/ha) Types of cold-resistant plants HORVW TRZAW BRSNN BEAVA ALOMY AVEFA BROTE lolpe POAAN CHEAL 250 10 20 100 100 60 80 40 80 thirty 100 125 0 10 100 100 thirty 70 20 80 10 100 60 0 0 100 90 20 60 10 70 10 100 thirty 0 0 90 90 0 50 20 70 0 100 15 0 0 90 100 0 thirty 20 60 0 1.0012 500 thirty 40 90 70 50 70 thirty 60 50 100 250 20 thirty 90 50 50 50 20 40 thirty 80 125 10 10 80 50 20 40 0 50 10 80 60 0 10 80 50 10 thirty 0 50 10 70 thirty 0 0 80 40 10 20 0 thirty 20 50 15 0 0 80 thirty 20 10 0 thirty 10 1.0018 500 0 0 100 100 0 10 20 50 10 80 250 0 0 100 100 0 10 20 50 0 70 125 0 0 100 100 0 0 0 40 0 70 60 0 0 80 80 0 0 0 40 0 thirty thirty 0 0 60 80 0 0 0 20 0 15 0 0 40 80 0 0 0 0 1.0024 500 40 50 100 60 60 60 thirty 70 90 90 250 20 thirty 90 50 50 50 10 70 80 90 125 10 20 90 40 thirty thirty 0 40 50 80 60 0 10 80 thirty 20 10 0 thirty 10 50 thirty 0 10 80 20 0 0 0 10 0 10 15 0 0 70 0 0 0 0 0 0 0 1.0042 500 250 0 0 40 20 10 0 0 10 10 10 125 0 0 20 10 10 0 0 0 0 0 60 0 0 thirty 0 0 0 0 0 0 0 thirty 0 0 thirty 0 0 0 0 0 0 0 15 0 0 thirty 0 0 0 0 0 0 0 1.0048 500 thirty 60 90 70 10 20 10 40 20 80 250 10 40 80 50 0 thirty 10 50 10 70 125 0 10 90 60 0 20 0 50 10 50 60 0 20 80 50 0 20 0 thirty 0 60 thirty 0 0 80 50 0 10 0 20 0 10 15 0 0 80 40 0 0 0 10 0 0 1.0066 500 10 0 100 60 10 10 10 20 20 80 250 10 0 90 50 10 0 0 thirty 0 50 125 0 0 90 thirty 0 0 0 10 0 40 60 0 0 90 10 0 0 0 10 0 20 thirty 0 0 90 0 0 0 0 0 0 0 15 0 0 70 0 0 0 0 0 0 0 1.0072 500 50 70 90 80 90 80 40 90 90 100 250 thirty 60 90 70 80 70 50 90 90 100 125 10 60 90 60 80 70 thirty 90 80 90 60 20 40 90 50 60 60 10 80 50 90

- 102 040613

thirty 0 thirty 80 40 thirty 40 0 70 40 90 15 0 0 80 40 10 10 0 50 10 60 500 60 70 90 100 90 90 20 90 90 90 250 thirty 50 90 70 80 80 10 80 90 90 125 20 50 80 60 70 70 0 60 90 60 10 20 90 70 70 50 0 50 80 80 thirty 0 20 80 70 40 20 0 40 70 70 15 0 0 70 50 10 0 0 20 10 500 0 10 90 40 50 20 10 60 50 80 250 0 10 80 40 40 10 0 40 50 80 125 0 0 80 20 thirty 0 0 thirty thirty 60 60 0 0 60 10 20 0 0 20 10 20 thirty 0 0 40 10 0 0 0 0 0 10 15 0 0 thirty 0 0 0 0 0 0 0 500 20 70 90 100 70 80 70 90 90 100 250 10 60 90 80 70 70 40 90 80 90 125 10 thirty 90 80 70 60 20 90 80 90 60 10 20 90 80 50 thirty 10 70 thirty 90 thirty 10 0 90 70 thirty 20 0 70 20 90 15 0 0 80 70 10 10 0 10 10 60 500 thirty 0 100 80 20 thirty 40 20 10 90 250 10 0 100 50 10 20 10 20 10 90 125 0 0 90 40 0 10 10 10 0 100 60 0 0 80 40 0 10 0 10 0 100 thirty 0 0 80 40 0 10 0 10 0 80 15 0 0 80 0 0 0 0 0 80 500 20 0 90 40 20 10 0 70 thirty 90 250 20 0 90 40 10 10 0 20 10 90 125 0 0 80 40 10 0 0 10 0 50 60 0 0 50 20 0 0 0 10 0 40 thirty 0 0 40 thirty 0 0 0 0 0 0 15 0 0 thirty thirty 0 0 0 0 0 0 500 80 80 90 90 90 90 90 90 90 100 250 80 80 90 90 90 90 80 90 90 100 125 40 70 90 90 80 80 80 90 90 90 60 20 60 90 80 80 80 70 70 80 90 thirty 20 thirty 90 70 60 60 thirty 70 70 90 15 10 20 90 80 20 thirty 20 60 20 500 80 80 90 90 90 90 70 90 90 100 250 40 50 90 90 80 90 60 90 90 90 125 40 20 90 90 80 80 50 90 80 70 60 10 20 90 80 70 60 20 90 80 thirty 10 10 90 80 thirty thirty 10 40 thirty 15 10 0 90 70 20 10 0 20 thirty 500 90 80 90 90 90 90 90 100 90 100

- 103 040613

250 80 70 90 80 90 90 80 90 90 100 125 70 60 90 80 80 90 70 90 90 90 60 20 40 90 80 70 40 60 80 80 90 thirty 10 10 90 80 50 20 20 20 70 90 15 0 0 90 80 20 0 0 10 20 500 60 70 90 90 90 90 70 90 70 100 250 thirty 60 90 90 80 90 60 90 80 100 125 20 thirty 90 80 80 80 thirty 90 90 100 60 20 20 90 80 50 70 10 80 70 90 thirty 10 0 80 80 50 70 0 70 40 90 15 10 0 80 90 20 thirty 0 40 20 80 500 10 50 90 70 40 80 10 90 60 90 250 10 thirty 90 70 60 70 10 80 70 90 125 10 20 90 70 thirty 70 0 70 60 90 60 10 10 80 60 thirty 60 0 60 20 90 thirty 0 10 80 60 10 40 0 50 10 90 15 0 0 80 70 10 thirty 0 40 0 90 500 20 50 90 80 60 60 20 40 80 80 250 20 0 90 60 70 60 10 50 70 70 125 0 0 90 50 40 40 0 40 80 80 60 0 0 90 40 50 40 0 50 80 80 thirty 0 0 70 40 50 thirty 0 40 70 60 15 0 0 80 thirty 10 10 0 thirty 50 60 500 50 60 100 100 50 90 60 70 250 thirty 40 100 100 thirty 90 40 70 125 10 thirty 90 100 20 70 thirty 60 60 10 10 80 100 20 60 40 40 thirty 0 0 60 100 10 thirty thirty 40 15 0 0 50 80 0 0 0 20 500 250 10 50 90 70 40 70 20 40 70 80 125 0 50 90 50 20 50 10 20 50 70 60 0 20 80 50 10 20 0 20 20 thirty 0 0 80 50 0 10 0 0 0 80 15 0 0 60 40 0 0 0 0 0 500 20 40 100 100 20 70 thirty 60 80 90 250 0 thirty 100 100 thirty 60 40 60 80 90 125 0 40 90 80 20 20 40 thirty 60 80 60 0 0 90 70 0 10 0 10 50 80 thirty 0 0 70 70 0 0 0 0 10 70 15 0 0 60 70 0 0 0 0 0

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Table 8

Control of some species of cold-resistant plants with compounds of formula (I) after post-emergence application

Connection ID Application rate (g/ha) Types of cold-resistant plants HORVW TRZAW POLCO KCHSC SINAR STEM GALAP VERPE 1.0001 500 20 20 100 80 100 100 90 90 250 10 20 100 80 100 100 90 90 125 0 10 100 70 90 100 80 80 60 0 0 100 50 90 80 80 thirty 0 0 100 40 90 100 70 15 0 0 90 thirty 90 100 20 60 1.0012 500 thirty 40 100 70 90 90 80 90 250 20 thirty 100 60 80 80 40 80 125 10 10 90 thirty 80 70 50 70 60 0 10 90 10 80 80 thirty 60 thirty 0 0 90 0 70 20 60 15 0 0 100 0 80 0 60 1.0018 500 0 0 100 60 100 100 90 90 250 0 0 100 60 90 90 90 90 125 0 0 100 40 90 90 60 80 60 0 0 90 10 40 90 80 thirty 0 0 100 10 20 90 20 70 15 0 0 80 0 20 80 0 40 1.0024 500 40 50 100 80 100 90 50 90 250 20 thirty 100 80 90 80 60 70 125 10 20 80 80 90 80 thirty 60 60 0 10 80 50 80 80 thirty thirty 0 10 80 thirty 80 70 20 15 0 0 70 10 80 50 10 1.0042 500 250 0 0 40 20 20 50 thirty 40 125 0 0 20 10 10 60 40 thirty 60 0 0 thirty 10 60 20 thirty thirty 0 0 thirty 0 10 60 20 20 15 0 0 0 0 0 thirty 0 20 1.0048 500 thirty 60 90 40 90 90 60 80 250 10 40 90 50 80 80 70 80 125 0 10 90 40 80 80 70 70 60 0 20 80 20 70 50 60 thirty 0 0 80 thirty 70 70 50 40 15 0 0 50 10 70 20 20 1.0066 500 10 0 80 70 80 70 40 40 250 10 0 60 60 80 70 50 20 125 0 0 50 80 70 thirty 20 60 0 0 20 60 40 10 thirty 0 0 0 70 50 thirty 0 15 0 0 0 40 thirty 20 0 1.0072 500 50 70 100 90 90 90 90 100 250 thirty 60 100 90 90 90 90 100

- 105 040613

125 10 60 100 80 80 90 50 90 60 20 40 70 70 80 60 80 thirty 0 thirty 90 thirty 70 20 70 15 0 0 90 20 70 thirty 60 500 60 70 100 60 100 100 90 90 250 thirty 50 100 thirty 80 90 70 90 125 20 50 100 thirty 70 80 60 80 60 10 20 90 20 80 40 80 thirty 0 20 90 0 70 70 50 15 0 0 90 0 50 80 thirty thirty 500 0 10 80 90 70 70 70 80 250 0 10 90 70 50 80 50 70 125 0 0 80 70 40 70 70 60 0 0 70 thirty 60 20 50 thirty 0 0 50 10 0 60 15 0 0 0 0 0 thirty 20 500 20 70 100 20 100 100 90 100 250 10 60 90 10 90 90 90 100 125 10 thirty 90 10 90 60 80 60 10 20 90 0 80 90 20 90 thirty 10 0 0 80 90 20 80 15 0 0 80 0 80 90 80 500 thirty 0 90 70 100 100 70 100 250 10 0 90 50 90 100 40 80 125 0 0 90 50 80 90 40 80 60 0 0 80 thirty 80 90 40 80 thirty 0 0 thirty 0 60 90 40 60 15 0 0 20 0 50 80 20 40 500 20 0 70 60 60 90 thirty 70 250 20 0 thirty 50 40 70 thirty 50 125 0 0 20 40 40 70 thirty 40 60 0 0 20 thirty thirty 40 thirty 40 thirty 0 0 10 20 20 40 20 thirty 15 0 0 10 10 0 20 10 20 500 80 80 100 60 90 100 90 100 250 80 80 90 thirty 90 100 80 100 125 40 70 90 20 90 100 80 100 60 20 60 90 10 90 90 60 100 thirty 20 thirty 80 10 90 100 thirty 90 15 10 20 80 0 80 100 10 80 500 80 80 90 80 90 100 80 100 250 40 50 90 50 90 100 60 100 125 40 20 90 20 90 100 60 80 60 10 20 90 10 80 90 50 90

- 106 040613

thirty 10 10 70 0 80 90 thirty 80 15 10 0 60 0 40 90 20 60 500 90 80 100 20 90 100 90 100 250 80 70 100 20 90 90 thirty 100 125 70 60 90 10 90 90 20 100 60 20 40 90 0 80 90 20 100 thirty 10 10 80 0 60 60 20 90 15 0 0 70 0 60 80 20 80 500 60 70 60 90 90 90 100 250 thirty 60 60 90 90 thirty 100 125 20 thirty 60 90 90 thirty 90 60 20 20 50 90 90 90 thirty 10 0 20 80 90 20 80 15 10 0 10 70 90 10 70 500 10 50 90 70 90 90 70 90 250 10 thirty 90 60 90 90 40 80 125 10 20 90 50 90 90 thirty 80 60 10 10 90 thirty 80 90 20 70 thirty 0 10 90 20 60 90 20 70 15 0 0 90 0 60 90 70 500 20 50 100 thirty 60 80 20 90 250 20 0 90 20 70 80 10 60 125 0 0 90 20 60 70 20 60 60 0 0 90 10 40 70 20 70 thirty 0 0 60 0 60 15 0 0 0 40 70 20 60 500 50 60 100 100 100 100 100 90 250 thirty 40 100 100 100 100 100 80 125 10 thirty 100 100 100 100 60 60 10 10 90 80 100 60 thirty 0 0 100 80 100 50 15 0 0 100 70 60 100 40 500 250 10 50 90 80 90 80 70 80 125 0 50 90 80 80 80 60 70 60 0 20 80 60 70 80 60 60 thirty 0 0 90 60 90 50 50 15 0 0 80 20 40 80 10 20 500 20 40 100 70 90 100 80 90 250 0 thirty 100 60 100 100 50 80 125 0 40 90 50 90 100 50 70 60 0 0 100 40 90 90 40 60 thirty 0 0 100 thirty 90 40 50 15 0 0 90 20 80 20 thirty

CLAIM

Claims (12)

1. Compound of formula (I) or a salt or N-oxide thereof, wherein R ¹ is selected from the group consisting of methyl, ethyl, n-propyl, cyclopropyl, propargyl, or C 1 haloalkyl; R ² is selected from the group consisting of hydrogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₃ alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ haloalkenyl, C ₂ -C ₆ alkynyl and C ₂ -C ₆ haloalkynyl; G is hydrogen or C(O)R ³ ; R ³ is selected from the group consisting of C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ -alkyl-S-, C ₁ -C ₆ -alkoxy , -NR ⁴ R ⁵ and phenyl optionally substituted with one or more R ⁶ ; R ⁴ and R ⁵ are independently selected from the group consisting of C ₁ -C ₆ alkyl and C ₁ -C ₆ alkoxy, or R ⁴ and R ⁵ together may form a morpholinyl ring; And R ⁶ is selected from the group consisting of halo, cyano, nitro, C ₁ -C ₃ alkyl, C ₁ -C ₃ haloalkyl, C1C ₃ alkoxy and C ₁ -C ₃ haloalkoxy; - 107 040613 each of X and Y independently represents hydrogen, C 1 -C ₃ -alkyl, C 1 -C ₃ -haloalkyl or halogen; D is a substituted or unsubstituted 5- or 6-membered monocyclic heteroaryl ring containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur, whereby if D is substituted, it is substituted on at least one carbon atom in the ring with R ⁸ and/or the nitrogen atom in the ring with R ⁹ ; each R ⁸ is independently oxygen, hydroxyl, halogen, cyano, C1-C ₆ alkyl, Ci-C ₆ haloalkyl, C1-C ₆ haloalkoxy, C1-C ₃ haloalkoxy-C1-C ₃ alkyl-, C1 -C ₆ -alkoxy, C1-C ₃ -alkoxyC1-C ₃ -alkyl, C1-C ₃ -alkoxy-C1-C ₃ -alkoxy-C1-C ₃ -alkyl-, C ₃ -Cb-cycloalkyl, C ₂ - Cb-alkenyl, C ₂ -Cbhaloalkenyl, C ₂ -C ₆ -alkynyl, C1-C ₆ -hydroxyalkyl-, C1-C ₆ -alkylcarbonyl-, C1-C ₆ -alkyl-8 (O) _t -, amino, C1 -C ₆ alkylamino, C1-C ₆ dialkylamino, -C(C ₁ -C ₃ alkyl)=X-O-C ₁ -C ₃ alkyl and C ₂ -C ₆ haloalkynyl; t is an integer equal to 0, 1 or 2; and each R ⁹ is independently C1- _C4 alkyl, _C3 - _C6 alkoxy, C1- _C2 alkoxy-C1- _C2 alkyl, _C2 - _C4 alkenyl, C1- _C4 haloalkyl , C ₂ -C ₄ haloalkenyl, C ₂ -C ₄ alkynyl or C ₂ -C ₄ haloalkynyl; or D is a substituted or unsubstituted phenyl ring (Dp) P (Dp) where p denotes the point of attachment (Dp) to the rest of the molecule; each of Z ¹ , Z ² , Z ³ , Z ⁴ and Z ⁵ is independently selected from the group consisting of hydrogen, cyano, amino, C1-C ₃ -dialkylamino, hydroxy, C1-C ₃ -alkyl, C1-C ₄ - alkoxy, C1- _C3 haloalkyl, C1- _C3 haloalkoxy and halogen; And ^R1 ? R ¹¹ R b and ρΐ2^£ΐ3 a gi5 W is either W1 or W2 or θW3 where a is the point of attachment to the phenylpyridazinedione/phenylpyridazinone moiety; b denotes the point of attachment to the ring D; each of R ¹⁰ , R ¹² , R ¹⁴ and R ¹⁵ independently represents hydrogen; each of R ¹¹ and R ¹³ independently represents hydrogen. 2. The compound according to claim 1, where G is hydrogen or -C(O)R ³ and R ³ is Ci-C ₄ alkyl, C ₂ -C ₃ -alkenyl, C ₂ -C ₃ -alkynyl, -C1 -C ₄ -alkoxy, -NR ⁴ R ⁵ where R ⁴ and R ⁵ together form a morpholinyl ring, or phenyl. 3. A compound according to claim 1 or 2, where G is hydrogen or C(O)R ³ , where R ³ is isopropyl, t-butyl, methyl, ethyl, propargyl, methoxy, ethoxy or t-butoxy. 4. A compound according to any one of the preceding claims, wherein X is hydrogen, halogen or C1-haloalkyl. 5. A compound according to any one of the preceding claims, wherein D is a substituted or unsubstituted pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyridyl, pyridonyl, pyrimidinyl, pyridazinyl, or pyrazinyl ring. 6. A compound according to any one of the preceding claims, wherein each R is independently oxo, C1- _C4 alkyl, C1- _C4 haloalkyl, halogen, cyano, hydroxyl, C1- _C4 alkoxy, or C1- _C4 alkylthio. . 7. A compound according to any one of claims 1 to 4, wherein D is Dp and each Z is independently selected from hydrogen, cyano, halogen, methyl, methoxy, and trifluoromethyl. 8. The connection according to any of the previous paragraphs, where W represents W1. 9. Connection according to any of the pi. 1-7 where W is W2. 10. Connection according to any of the pi. 1-7 where W is W3. I. A herbicidal composition containing a herbicidal compound according to any one of pi. 1-10 and an agriculturally acceptable aid. 12. A method for controlling the growth of unwanted plants, comprising applying a compound of formula (I) according to any one of claims 1 to 10 or a herbicidal composition according to claim 11 in relation to the unwanted plants or their place of growth. 13. Use of a compound of formula (I) according to any one of claims 1 to 10 as a herbicide.