SK102296A3 - Phenylthio acetic acid derivatives, process and intermediate products for their production and agent containing them - Google Patents

Abstract

Phenylthio acetic acid derivatives of formula (I) in which the components and index have the following meanings: R<1> is hydrogen and alkyl; R<2> is cyano, nitro, trifluoro methyl, halogen, alkyl and alkoxy; m is 0, 1 or 2, in which the radicals R<2> may be different if m is 2; R<3> is hydrogen, cyano, nitro, hydroxy, amino, halogen, alkyl, halogen alkyl, alkoxy, halogen alkoxy, alkylthio, alkylamino or dialkylamino; R<4> is hydrogen, cyano, nitro, hydroxy, amino, halogen, possibly substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkenyloxy, alkenylthio, alkenylamino, N-alkenyl-N-alkylamino, alkinyl, alkinyloxy, alkinylthio, alkinylamino, N-alkinyl-N-alkylamino, possibly substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, N-cycloalkyl-N-alkylamino, cycloalkenyl, cycloalkenyloxy, cycloalkenylthio, cycloalkenylamino, N-cycloalkenyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-N-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-N-alkylamino; R<5> is hydrogen, possibly substituted alkyl, cycloalkyl, alkenyl, alkinyl, alkyl carbonyl, alkenyl carbonyl, alkinyl carbonyl or alkyl sulphonyl, possibly substituted aryl, aryl carbonyl, aryl sulphonyl, hetaryl, hetaryl carbonyl or hetaryl sulphonyl. The invention also concern their salts, the process and intermediate products for their production and their use.

Description

Phenylthioacetic acid derivatives, process and intermediates therefor and compositions containing them

Technical field

The present invention relates to phenylthioacetic acid derivatives of the general formula I ΐνose -% «

R ⁵ ON = C (R ⁴ ) -C (R ³ ) = no ₂ (R ² ) m (I) c = nock ₃

Oxic-SR ¹ wherein the substituents and the index have the following meanings:

R ¹ is hydrogen and C 1 -C 4 -alkyl.

R ² is cyano, nitro, trifluoromethyl, halogen,

C ₁ -C ₄ -alkyl and C ₁ -C ₄ -alkoxy

m is 0, 1 or 2, wherein the radicals R ² may be the same or different if m is 2, q

R is hydrogen, cyano, nitro, hydroxy, amino, halogen,

_C1-C4-alkyl, C ^ C haloalkyl, C ₁ -C ₄ -alkoxy, C ₁ ~ C ₄ -haloalkoxy, C ₁ -C _4- alkylthio, C ₁ -C _4- alkylamino or di-C _4-C ^ alkylamino,

R 6 represents hydrogen, cyano, nitro, hydroxy, amino, halogen,

C ₁ -C-alkyl, Cj-Cg-alkoxy, C ^ -C alkylthio, C -C -alkylamino, di-C ^ -C-alkyl amino, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ alkenyloxy C ₂ -C-alkenylthio, C ₂ -C -alkenylamino, NC ₂ -C alkenyl-C - ^ - C-amino, C ₂ -C-alkynyl, C ₂ -C-alkynyloxy, C ₂ -C ₆ - alkynylthio, C ₂ -C ₆ -alkinylamino, NC ₂ -C-alkynyl-NC ₁ -C-akylamino, the hydrocarbon radicals of these groups being partially or fully halogenated or may carry one to three of the following radicals: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C ₁ -C-alkylaminocarbonyl, di-C -C-alkylaminocarbonyl, C ^^ - Cg-alkylaminothiocarbonyl, di-Cl--alkylaminothiocarbonyl, C ^ -C-alkylsulfonyl , C - ^ - Cg-alkylsulfonyl, C ^ -C alkoxy, C-PCG-haloalkoxy, C -C alkoxycarbonyl, C ^ -C alkylthio, C ^ -C-alkylamino, di-C ₁ -C-alkyl amino , C ₂ -C 8 -alkenyloxy, C ₃ -C 8 -cycloalkyl, C ₃ -C 8 -cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C ₁ -C ₄ -alkoxy, arylthio, aryl-C 1-6 -alkyl; -C 1-4 alkylthio, hetaryl, hetaryloxy, hetaryl-C ₁ -C ₄ -alkoxy, hetarylthio, hetaryl-C ₁ -C ₄ -alkylthio, wherein the cyclic moieties may on their side be halogenated partially or fully and / or carry up to three the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkylsulfonyl, C ₃ -C 8 -cycloalkyl, C ₁ - C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di- C 1 -C 8 -alkylaminocarbonyl, C 1 -C 8 -alkylaminothiocarbonyl, di-C 1 -C 8 -alkylaminothiocarbonyl, C ₂ -C 8 -alkenyl, C ₂ -C 8 -alkenyl, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetarylthio and C (= NOR ⁶ ) -A _n -R ⁷ ,

C ₃ -C 8 -cycloalkyl, C ₃ -C 8 -cycloalkyloxy, C ₃ -C 8 -cycloalkylthio, C ₃ -C 8 -cycloalkylamino, NC ₃ -C 8 -cycloalkyl-NC ₁ -C 8 -alkylamino, C ₃ -C 8 -cycloalkenyl> C ₃ -C 8 -cycloalkenyloxy, C ₃ -C 8 -cycloalkenylthio, C ₃ -C 8 -cycloalkenylamino, NC ₃ -C 8 -cycloalkenyl-N -C 8 -C 8 -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-NC-C 8 -C 8 -alkylamino, aryl, arylthio, arylamino, N-aryl-NC-C8-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-NC-C8-alkylamino, wherein the cyclic radicals may be partially or fully halogenated, or carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, amino-3 carbonyl, aminocarbonyl, halogen, C ₁ -C ₆ alkyl, C ^ -C haloalkyl, Cy-Cg-alkylasulfonyl, C ^ -C-alkylsulfonyloxy, C ₃ -C-cycloalkyl, _C1 ~ Cg alkoxy, C ^ -C -haloalkoxy, C - ^ - C alkoxycarbonyl, C - ^ - Cg alkylthio, C - ^ - C-amino, di-C 1 -C 8 -alkylamino, C 1 -C 8 -alkylaminocarbonyl, di-C ₁ -C 8 -alkylamino rbonyl, C ^ -C-alkylaminothiocarbonyl, di-C ^ -C-alkylaminothiocarbonyl, C ₂ -C alkenyl, C ₂ -C alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy;

R ⁵ represents hydrogen, C 1 -C 10 -alkyl, C 3 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkylcarbonyl, C 2 ^-C 10 -acenylcarbonyl, C 3 -C ₁₀ -alkinylkarbonyl ^c i ^"c IC" -alkylsulfonyl, where the radicals may be partially or fully halogenated or to carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, CJ C ₁ -C 8 -alkyl, C ₁ -C 8 -haloalkyl, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -alkylsulfonyloxy, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkoxy alkylthio, C - ^ - Cg-alkylamino, _di-C1 ~ Cg-alkylamino, C ^^ - Cg-alkylaminocarbonyl, di-C ^ -C-alkylaminocarbonyl, C - ^ - C-alkylaminothiocarbonyl, di-C ^ -C -alkylaminothiocarbonyl, C ₂ -C 8 -alkenyl, C ₂ -C 8 -alkenyloxy, C ₃ -C 8 -cycloalkyl, C ₃ -C 8 -cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl and hetaryloxy, the cyclic groups on their side may be partially or fully halogenated or carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkylsulfonyl, C 1 -C 6 -alkylsulfonyl; C1-C6-alkylsulfonyloxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino , -C ^ C-alkylaminocarbonyl, di-C ₁ -C-alkylaminookarbonyl, C ^ -C-alkylaminothiocarbonyl, di-C ^^ - -alkylaminothiocarbonyl, C ₂ -C alkenyl, C ₂ -C alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarythio or C (= NOR ⁶ ) -A _n -R ⁷ ;

aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, which radicals may be partially or completely hydrogenated or carry one to three of the following: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C- _L -C alkyl, C ₁ -C haloalkyl, Cy-Cg-alkylcarbonyl, C ^ -C alkylsulfonyl, C ₁ -C-alkylsulfonyloxy, C ₃ -C ₆ cycloalkyl, C ^ -C alkoxy, C C 1 -C 8 -haloalkoxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkylthio, C 1 -C 8 -alkylamino, di-C 1 -C 8 -alkylamino, C 1 -C 8 -alkylaminocarbonyl, di-C 1 -C 8 -alkylaminocarbonyl , C - ^ - C-alkylaminothiocarbonyl, di-C ₁ ~ -C-alkylaminothiocarbonyl, C2-Cg alkenyl, C ₂ -C alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy or C (= NOR ⁶ ) -A _n -R ⁷ ;

while

A represents oxygen, sulfur or nitrogen and nitrogen carries hydrogen or C1-C6-alkyl;

n is 0 or 1;

R is hydrogen or C1-C6-alkyl and

R ⁷ is hydrogen or C 1 -C 6 -alkyl, and salts thereof.

In addition, the invention relates to a process and intermediates for the production of these compounds as well as compositions for controlling animal pests and harmful fungi.

BACKGROUND OF THE INVENTION

Phenylacetic acid derivatives for pest control are known from the literature (EP-A 432 503, EP-A 463 488).

It was an object of the present invention to provide novel compounds with improved activity.

SUMMARY OF THE INVENTION

Therefore, the above-defined phenylacetic acid derivatives of the general formula I have been found. In addition, a process for their preparation and intermediates thereof as well as means for destroying animal pests and harmful fungi and their use in this sense have been found.

The compounds of formula I can be prepared by various methods known in the literature.

In principle, it is immaterial in the synthesis of compounds of formula I whether a group of formula -C (NOCH ₃ J-COSR ¹⁾ or a group -CH ₂ ON = C (R ³ ) -C (R ⁴ ) = NOR ⁵ was first formed.

The formation of the -C (NOCH ₃₎ J-COSR ¹ moiety is known, for example, from the literature cited above.

The type of synthesis -CH ₂ ON = C (R ³ ) -C (R ⁴ ) = NO ^{5 of the} side chain essentially depends on the type of substituents R ³ and R ⁴ .

1. In the case where R ³ and R ^{4 are} not halogen, the formation of -CH ₂ ON = C (R ³ ) -C (R ⁴ ) = NOR ⁵ is carried out by reacting the benzyl derivative of formula II with a hydroxyimine of formula III

R ⁵ -ON = C (R ⁴ ) -C (R ³ ) = NOH (III)

(II)

O = C-SR ¹ 10 - ^{(r 2} '

R5-0N = C ^(R4) -C ^(R3) = NOCH 2 ^ J ^ (I) C = _NOCH3

O = C-SR1 wherein L ¹ in formula II represents a nucleophilic exchangeable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base, for example sodium hydride, potassium hydroxide, potassium carbonate and triethylamine, according to the methods described in Houben-Weyl, Volume E14b, p. 370f and Houben Weyl, vol. 10/1, p. 1189f.

Said hydroxyimine of formula III is obtained by reacting the corresponding dihydroxyimine of formula IV with a nucleophilically substituted reagent of formula VI

R ⁵ -L ² + HON = C (R ⁴ ) -C (R ³ ) = NOH (VI) (IV)

-> R ⁵ -ON = C (R ⁴ ) -C (R ³ ) = NOH (III) wherein L in formula VI represents a nucleophilically replaceable leaving group, for example halogen or sulfonate groups, preferably chlorine, bromine, iodine, mesylate, tosylate or triflate.

The reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base such as potassium carbonate, potassium hydroxide, sodium hydride, pyridine and triethylamine according to the methods described in Houben Weyl, Volume E 14b, p. 307f and p. 385F; Houben Weyl, vol. 10/4, p. 55f, p. 180f and p. 217F; Houben Weyl, vol. E5, p. 780f.

Alternatively, the compounds of formula I may also be obtained by first reacting a benzyl derivative of formula II with a dihydroxyiminoderivative of formula IV to the corresponding benzyloxime derivative of formula V, then reacting the compound of formula V with a nucleophilically substituting agent of formula VI to compounds of formula I.

HON = C ^(R4) -C ^(R3) = NOH (IV)

(II)

O = C-SR ³ m

R ⁵ -L ²

R ⁵ -ON = C (R ⁴ ) -C (R ³ ) = NOCH ₂ (I) (R ² ) mc = noch ₃

The CHC-SRR reaction is carried out in a manner known per se in an inert organic solvent in the presence of a base such as potassium carbonate, potassium hydroxide, sodium hydroxide, pyridine and triethylamine according to the methods described in Houben Weyl, vol. 1189f; Houben Weyl, vol. E 14b, p. 307f and p. 385F; Houben Weyl, vol. E5, p. 780f.

1.2 Analogously, the required hydroxyimine of formula III can also be prepared from a carbonylhydroxyimine of formula VIIa by reaction with a hydroxylamine of formula IXa or a salt thereof of formula IXb.

IR ⁵ -ONH ₂ L (IXa) I ^bzw · i + O = C (R 4) -C (R 3) ₌ NOH

R ⁵ -ONH ₃ ®q® I (villa) (IXb) /

-► R ^S -ON = C (R ⁴ ) -C (R ³ ) = NOH (III)

Q 'in formula IXb represents an anion of an acid, in particular an inorganic acid, for example a halide such as chloride.

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 513 580;

• Houben Weyl, vol. 10/4, p. 369f and p. 385F;

Alternatively, the compounds of formula I can also be obtained by first reacting a benzyl derivative of formula II with a carbonyl hydroxyimino derivative of formula VIIa to the corresponding benzyloxyimine of formula VII, and then reacting with the hydroxylamine of formula IXa or its salt of formula IXb to form a compound of formula I.

O = C (R ⁴ ) -C (R ³ ) = NOH

_II-2 CH

(R ² ), (Vila) c = no ₃ , (II)

O = C-SRI

IXa / IXb

-

R ⁵ -ON = C (R ⁴ ) -C (R 3) = NOCH ₂ (R ² ) mc = noch ₃

O = C-SRI

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in Houben Weyl, Volume E 14b, p. 369f; Houben Weyl, vol. 10/1, p. 1189f and Houben Weyl, vol. 10/4, p. 73f or EP-A 513,580.

1.4 Another possibility of preparing compounds of formula I is by reacting the benzyl derivative of formula II with N-hydroxyphthalimide followed by hydrazinolysis to the benzylhydroxylamine of formula IIa and further reacting the compound of formula IIa with a carbonyl compound of formula X.

O = C-SR ¹

OxiC-SR ¹

R = -0N = C ^(R4) -C ^(R3) = H (Ha) (Ha) (I) (x)

The reaction is carried out in a manner known per se in an inert organic solvent according to the methods described in EP-A 463 488 and DE-application no. 4 228 867.3.

The necessary carbonyl compound of formula X is obtained, for example, by reaction of the corresponding hydroxyiminocarbonyl of formula VIIIb and a nucleophilically substituted reagent of formula VI

R ⁵ -L ² + HON = C (R ⁴ ) -C (R ³ ) = O-> R ⁵ -ON = C (R ⁴ ) -C (R ³ ) = 0 (VI) (VIIb) (x) or by reacting the corresponding dicarbonyl compound of formula XI with a hydroxylamine of formula IXa or a salt thereof of formula IXb

R ⁵ -ONH _{2 '} (IXa) bzw. 1 + O = C (R ⁴ ) -C (R 3) = O

R ⁵ -ONH3®Q® J (ixb) /

- >> ^R5 -ON = C ^(R4) -C ^(R3) = 0 (x)

The reaction is carried out in a manner known per se in an organic solvent according to the methods described in EP-A 513 580, Houben Weyl, vol. 10/4, p. 55f, p. 73f, p. 180f and p. 217f, Houben Weyl, vol. E5, p. 780f.

1.5 In addition, compounds of formula I can also be obtained by first reacting benzylhydroxylamine with a hydroxyiminocarbonyl of formula VIIIb to the corresponding benzyloxyimine of formula V, wherein the compound of formula V is then reacted with a nucleophile-substituting agent of formula VI as described Formula I.

H 0 N = C (R ⁴ ) -C (R ³ ) = O

ÍVIIb)

O = C-SRI (R ²⁾

HON = C ^(R4) -C ^(R3) = N0-CH2 (A)

C = NOCH ₃

I,

O = C-SR?

R5-L2

₃ ÄJ ^(R2)

R ^a ON = C ^(R4) -C ^(R3) = CH2 N0 |

C = NOCH ₃ (X)

OsC-SR ¹

1.6 Analogously, the compounds of formula I can also be prepared by first converting a benzylhydroxylamine of formula IIa with a dicarbonyl of formula XI to a benzyloxyimine of formula VIII and then reacting the compound of formula VIII with a hydroxylamine of formula IXa or a salt thereof of formula IXb Formula I.

O = C (R ⁴ ) -C (R ³ ) = O (xD

CHC-SR ¹ (R ²⁾ m

IXa / IXb

O = C ^(R4) -C ^(R3) = N-OCH ₂ (VIII)

C = NOCH ₃

I

O = C-SR ¹ (R ² ) m

R ⁵ O = C (R 4) -c (R ³ ) = NO-CH ₂

CD c = noch ₃

O = C-SRI

2. The compounds wherein ^R3 and / or ^R4 represent a halogen atom are obtained from the corresponding precursors where the radical concerned is a hydroxyl group, (Houben-Weyl, Volume E5, pp. 631; J. Org. Chem. 36, 233 ( J. Org. Chem., 57, 3245 (1992), preferably the corresponding reactions to the halogen derivative are carried out in Steps I and VIII.

3. Compounds in which R ³ and / or R ⁴ are attached to the radical through an O-, S- or N-atom are obtained from the corresponding precursors in which the respective radical is a halogen atom by known methods (see Houben-Weyl, Part E5, pages 826f and 1280f, J. Org. Chem., 36, 233 (1971), J. Org. Chem., 46, 3623 (1981). Preferably, the corresponding conversions to the halogen derivative are carried out in stages I and VIII. .

4. Compounds in which R ³ and / or R ⁴ are bonded to the radical through an oxygen atom are also obtained, for example, from the corresponding precursors in which the corresponding radical is a hydroxy group by conventional methods (see Houben-Weyl, vol. E5, p. 826). Aust J. Chem., 27, 1341-9 (1974), preferably the corresponding conversions to alkoxy derivatives are carried out in stages I and VII.

5. Compounds in which R ^{3 is} not halogen are preferably obtained by first converting a compound of formula X with the lactone of formula XII with the method described in EP-A 493 711 to the corresponding benzoacid of formula XIII and converting the compound of formula XIII via a halide to cyanocarboxylic acids of formula XIV, which are then subjected to the Pinner reaction (Angew. Chem. 94, 1 (1982)), which is converted to the α-keto ester of formula XV. The corresponding thioester is obtained from the derivatives of formula XV by re-esterification, which is then converted to the compounds of formula I.

R ^S -ON = C ^(R4) -C ^(R3) = N0H +

(R ²⁾ m (X) (x n)

(Hal = halogen)

C = 0 (XIV ')

CN

R ⁵ -ON = C (R ⁴ ) -C (R ³ ) = NO-CH ₂ (xv) • jj "( ^r2 ) m \ <R * H>

C = 0 C ₂ R (R ² ) m

R ⁵ -ON = C (R ⁴ ) -C (R ³ ) = NO-CH ₂

cxvi)

C = 0

O = C-SR ³

(R ² )

O = C-SR ³

6. By another embodiment of the process, compounds of formula I are also obtained, for example, starting from compounds of formula XV in which the keto group is first converted to the oxime and then the ester function via the carboxylic acid buc directly or after activation (formation of e.g. carboxylic acid chloride) , is converted to the corresponding thioester (Organikum, 16th Ed., pp. 415, 423 and 622 (1985)).

C = 0

co ₂ r

R ^s -ON = C (R ⁴ ) -C (R ³ ) = NO-CH ₂ '(RXH) (xv>

s

R ⁵ -ON = C (R ⁴ ) -C (R ³ ) (XV)

I

R ⁵ -ON = C (R ⁴ ) -C (R ³ ) = NO-CH ₂

I ω

The compounds of formula II can be prepared by the methods described in EP-A 432 503, EP-A 463 488, EP-A 386 561.

The compounds of the formula I can be obtained in the manufacture, in view of their C = C and C = N double bonds, as an E / Z-mixture of isomers, which can be separated, for example, by crystallization or chromatography in the usual manner.

However, if mixtures of isomers are obtained in the synthesis, separation is generally not necessary, since the individual isomers may vary with each other during processing for use or in use (for example by exposure to light, acid or base). Such changes may also occur after use, for example in the treatment of plants in treated plants or in harmful fungi or animal pests.

With respect to the C = NOCH ₃ double bond, the E-isomers of the compounds of formula I are more preferred (configuration relative to the -OCH ₃ group relative to the -COSR ¹ group).

With respect to the -C (R ³ ) = NOCH 2 - double bond, the potency of the cis-isomers of the compounds of formula I (configuration relative to the remainder of the R ³ relative to the -OCH 2 - group) is more preferred.

In the above definitions of the compounds of formula I, collective terms are used which generally represent the following groups:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: straight or branched alkyl groups having 1 to 4, 6 or 10 carbon atoms, e.g. C 1 -C 8 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,

2.2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,

1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,

4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,

1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

alkylamino: an amino group bearing a straight or branched (C 1 -C 6) alkyl group as defined above;

dialkylamino: an amino group which carries two independent straight or branched alkyl groups each having from 1 to 6 carbon atoms as mentioned above;

alkylcarbonyl: straight or branched (C 1 -C 10) alkyl groups attached to the residue via a carbonyl (-CO-) group;

alkylsulfonyl: straight or branched alkyl groups having 1 to 6 or 10 carbon atoms which are bonded to the residue via a sulfonyl group (-S (= O) ₂ -);

alkylsulfoxyl: straight or branched (C 1 -C 6) alkyl groups which are bonded to the residue via a sulfoxyl group (—S (= O) -);

alkylaminocarbonyl: (C 1 -C 6) alkylamino as defined above which are attached to the residue via a carbonyl (-CO-) group;

dialkylaminocarbonyl: dialkylamino groups each having 1 to 6 carbon atoms on the alkyl radical as mentioned above, which are attached to the radical via a carbonyl (-CO-) group;

alkylaminothiocarbonyl: (C 1 -C 6) alkylamino as defined above, which are bonded to the residue via a thiocarbonyl (-CS-) group;

dialkylaminothiocarbonyl: dialkylamino groups in each case having 1 to 6 carbon atoms in the alkyl radical as mentioned above, which are attached to the radical via a thiocarbonyl (-CS-) group;

haloalkyl: straight or branched (C 1 -C 6) alkyl groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms, for example C ₁ -C ₂ -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, trifluoromethyl, , dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl,

2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,

2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

alkoxy: straight or branched alkyl groups having 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the residue via an oxygen atom (-O-), e.g. C 1 -C 8 -alkoxy such as methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy, 1-methylpropoxy, 2-methylpropyloxy, 1,1-dimethyletyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 2, 2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1,1-dimethylpropyloxy, 1,2-dimethylpropyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 1,2,2-trimethylpropyloxy, 1- ethyl-1-methylpropyloxy and 1-ethyl-2-methylpropyloxy;

alkoxycarbonyl: straight or branched (C 1 -C 6) alkyl groups attached to the residue via an oxycarbonyl (-OC (= O) -) group;

haloalkoxy: straight or branched (C 1 -C 6) alkyl groups in which the hydrogen atoms are partially or fully replaced by halogen atoms as mentioned above;

alkylthio: straight or branched alkyl groups having 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the residue via a sulfur atom (-S-), for example C 1 -C 8 -alkylthio such as methylthio, ethylthio, propylthio -methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio,

1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio,

1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3- dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,

1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio;

cycloalkyl: monocyclic alkyl groups having 3 to 6 ring members, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

alkenyl: straight or branched alkenyl groups having 2 to 6 or 10 carbon atoms and one double bond at any position, for example C ₂ -C ₆ -alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methyletenyl, 1-butenyl, 2-Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3- pentenyl, 4-pentenyl,

1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1- methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2- propenyl,

1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,

3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,

2-methyl-2-pentenyl, 1-methyl-3-pentenyl,

3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl -2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl -1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl -2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl , 1-ethyl-3-butenyl,

2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1- ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl,

4-methyl-1-pentenyl, 1-methyl-3-methyl-2-pentenyl, 4-methyl-2-methyl-3-pentenyl, 3-methyl-2-pentenyl, -2-pentenyl, alkenyloxy: straight or branched alkenyl groups with 2 up to 6 carbon atoms and a double bond at any position attached to the remainder via an oxygen atom (—O-);

alkenylcarbonyl: straight or branched alkenyl groups having 2 to 10 carbon atoms and one double bond at any position, which are bonded to the residue via a carbonyl group (-CO-);

alkenyltio resp. alkenylamino: straight or branched alkenyl groups having 2 to 6 carbon atoms and one double bond at any position, which are bonded to the residue (alkenylthio) via a sulfur atom or (alkenylamino) via a nitrogen atom;

alkynyl: straight or branched alkenyl groups of 2 to 10 carbon atoms and one triple bond at any position, for example C ₂ -C 8 -alkynyl such as ethynyl, 1-propynyl, 2-butynyl,

3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1- methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3- butynyl and 1-ethyl-1-methyl-2-propynyl;

alkynylcarbonyl: straight or branched alkynyl groups of 3 to 10 carbon atoms and one triple bond at any position, which are bonded to the residue via a carbonyl group (-CO-);

alkynyloxy resp. alkynylthio and alkynylamino: straight or branched alkynyl groups having 2 to 6 carbon atoms and one triple bond at any position, which are bonded to the residue via an (alkynyloxy) oxygen atom or (alkynylthio) via a sulfur atom or (alkynylamino) via a nitrogen atom;

cycloalkoxy resp. cycloalkythio and cycloalkylamino: monocyclic alkenyl groups having 3 to 6 carbon ring members which are bonded to the (cycloalkyloxy) radical through an oxygen atom or (cycloalkythio) sulfur atom or (cycloalkylamino) via a nitrogen atom, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

cycloalkenyl; cycloalkenyloxy, cycloalkenylthio and cycloalkenylamino: monocyclic alkenyl groups of 3 to 6 carbon atoms which are attached to the residue directly optionally (cycloalkenyloxy) via an oxygen atom or (cycloalkenylthio) sulfur atom or by 20 or (cycloalkenylamino) via a nitrogen atom, for example cyclopropenyl, cyclobutenyl, cyclop or cyclohexenyl;

heterocyclyl resp. heterocyclyloxy, heterocyclylthio and heterocyclylamino: three to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles containing one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur and which are bonded to the remainder directly (heterocyclyloxy) via an oxygen atom or (heterocyclylthio) via a sulfur atom or (heterocyclylamino) through a nitrogen atom, for example 2-tetrahydrofuranyl, oxiranyl, 3-tetrahydrofuran,

2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl,

3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 5-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl,

4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl,

5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1, 2,4-thiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiazolidin-2-yl, 1,3, 4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,3-dihydro-fur-4-yl, 2,3-dihydrofur-5-yl, 2,5-dihydrofur-2-yl, 2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl,

2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2, 5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl,

2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisothiazol-4-yl,

2,5-dihydroisothiazol-5-yl, 2,3-dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazol-4-yl, 2,3-dihydroisopyrazol-5-yl, 4,5-dihydroisopyrazol-3-yl, 4, 5-dihydroisopyrazol-4-yl, 4,5-dihydroisopyrazol-5-yl, 2,5-dihydroisopyrazol-3-yl, 2,5-dihydroisopyrazol-4-yl, 2,5-dihydroisopyrazol-5-yl, 2, 3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-3-yl, 4,5-dihydrooxazol-4-yl, 4, 5-Dihydrooxazol-5-yl, 2,5-dihydrooxazol-3-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-521

-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydro-thiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4 yl,

4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl,

2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2, 5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3- tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl,

1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl,

1,3-dihydrooxazin-2-yl, 1,3-dithien-2-yl, 2-tetrahydropyranyl,

1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazol-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1- dioxo-2,3,4-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl,

1,3-dihydrooxazin-2-yl, 1,3-dithien-2-yl;

aryl aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon radicals which are attached to the skeleton directly optionally (aryloxy) via an oxygen atom (-O-) or (arylthio) sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) via a sulfonyl group (-SO ₂ -), for example, phenyl, naphthyl and phenatrenyl or phenyloxy, naphthyloxy and phenatrenyloxy and the corresponding carbonyl and sulfonyl radicals;

arylamino: aromatic mono- or polycyclic hydrocarbon radicals which are attached to the skeleton via a nitrogen atom;

hetaryl resp. hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which, in addition to the carbon ring members, may additionally contain one to four nitrogen atoms or one to three nitrogen atoms and an oxygen or sulfur atom or one oxygen and one sulfur atom and which are attached directly to the skeleton optionally (hetaryloxy) through an oxygen atom (-0-) or (hetarythio) sulfur atom (-S-), (het22 arylcarbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a sulfonyl group (- SO ₂ -), for example

5-membered heteroaryl containing one to three nitrogen atoms: heteroaryl groups with five ring members which, in addition to the carbon atoms, may contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl,

5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl and 1,3,4-triazol-2-yl;

5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or one oxygen or one sulfur atom:

heteroaryl groups with five ring members which, in addition to the carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and a sulfur or oxygen atom or one oxygen or sulfur atom as a ring member, for example 2-furyl,

3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl,

5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,

1,2,4-triazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl,

1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;

benzocondensed 5-membered heteroaryl containing up to three nitrogen atoms or one nitrogen atom and / or one oxygen or sulfur atom:

five-membered heteroaryl groups which, in addition to the carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen atom or one sulfur atom as ring members and in which two adjacent carbon ring members or nitrogen atoms and the adjacent carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group;

a nitrogen-linked 5-membered heteroaryl containing one to four nitrogen atoms, or a nitrogen-linked benzocondensed

5-membered heteroaryl containing one to three nitrogen atoms: heteroaryl groups with five ring members which, in addition to carbon atoms, may contain one to three nitrogen atoms as ring members and wherein two adjacent ring carbons or nitrogen and the adjacent ring carbon member may be bridged A -1,3-diene-1,4-diyl group, the rings being attached to the skeleton via a nitrogen ring member;

6-membered heteroaryl containing one to three or one to four nitrogen atoms:

six-membered heteroaryl groups which may contain, in addition to carbon atoms, one to three or one to four nitrogen atoms, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4- pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazinyl;

benzocondensed 6-membered heteroaryl containing one to four nitrogen atoms:

six-membered heteroaryl groups in which two adjacent carbon ring members may be bridged by a buta-1,3-diene-1,4-diyl group, for example quinoline, isoquinoline, quinazoline and quinoxaline, optionally corresponding to oxy-, thio-, carbonyl - or sulfonyl groups.

Hetarylamino: aromatic mono- or polycyclic radicals which, in addition to the carbon ring members, may contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom and which are attached to the skeleton through a nitrogen atom.

Partially or fully halogenated indicates that in the group so designated, the hydrogen atoms may be partially or completely replaced by the same or different halogen atoms.

In view of their biological activity, compounds of formula I in which m is 0 are preferred.

Also preferred are compounds of formula I wherein R ¹ is methyl.

Further preferred are compounds of formula I wherein R ³ is hydrogen, hydroxy, cyclopropyl, chloro, methyl, ethyl, 1-methylethyl, methoxy, methylthio or phenyl.

Moreover preferred are compounds of formula I, wherein R ³ is methyl.

Other preferred compounds of formula I are those in which

O _#

R is methoxy.

In addition, preferred compounds of formula I wherein R ³ is hydroxy.

Other preferred compounds of formula I are those wherein R ³ is chlorine.

Other preferred compounds of formula I are those wherein R ⁴ is hydrogen, hydroxy, cyclopropyl, chloro, methyl, ethyl, isopropyl, methoxy or methylthio.

Further preferred are compounds of formula I wherein R ⁴ is methyl.

Further preferred are compounds of formula I wherein R ⁴ is methoxy.

Further preferred are compounds of formula I wherein R ⁴ is hydroxy.

Further preferred are compounds of formula I wherein R ⁴ is ethyl.

Further preferred are compounds of formula I wherein R ⁴ is isopropyl.

Further preferred are compounds of formula I wherein R ⁴ is cyclopropyl.

Further preferred are compounds of formula I wherein R ⁴ is aryl or hetaryl.

Further preferred are compounds of formula I wherein R ⁴ is phenyl.

Moreover preferred are compounds of formula I, wherein R ⁵ is methyl or ethyl.

Further preferred are compounds of formula I wherein R ⁵ is arylalkyl or heteroarylalkyl.

Further preferred are compounds of formula I wherein R ⁵ is aryloxyalkyl or heteroaryloxyalkyl.

Further preferred are compounds of formula I wherein R ⁴ is optionally substituted aryl or hetaryl.

Further preferred are compounds of formula I wherein R ⁴ is optionally substituted pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.

Further preferred are compounds of formula I wherein R ⁴ is optionally substituted furyl, thienyl or pyrrolyl.

Further preferred are compounds of formula I wherein R ⁴ is optionally substituted oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.

Further preferred are compounds of formula I wherein R ⁴ is optionally substituted oxadiazole, thiadiazolyl or triazolyl.

Further preferred are compounds of formula I wherein R ⁴ is phenyl which is unsubstituted or carries one or two of the following: nitro, cyano, hydroxy, amino, aminocarbonyl, aminothiocarbonyl, halogen, C ₁ -C ₄ -alkyl, C ₁ - C ₄ haloalkyl, C ₁ ~ C ₄ alkoxy, C? -C? haloalkoxy, C? -C? -alkylamino, di-C ₁ ~ C ₄ -alkylamino, C ₁ -C _4- alkylsulfonyl, C ₁ - C ₄ -alkoxycarbonyl, C ₁ -C ₄ -alkylaminocarbonyl or di-C ₁ -C ₄ -alkylaminocarbonyl.

Further preferred are compounds of formula I wherein R ⁵ is aryl or hetaryl.

The compounds of the formula I which are particularly advantageous in respect of their use are listed in the following tables.

Tabuika 1

Compounds of general formula 1.1 wherein (R ² ) _m is hydrogen

O Λ (T and the combination of substituents R, R and R for each compound have the meaning given in one row of Table A

R ⁵ ON

OCH ₂ (1.1)

Tabuika 2

Compounds of formula 1.1 in which (R ² ) _m is chlorine and combinations of substituents R ³ , R ⁴ and R ⁵ for each compound have the meaning given in one row of Table A.

Table A

no. R ³ R ⁴ R ⁵ 1 ch ₃ ch ₃ H 2 ch ₃ ch ₃ ch ₃ 3 ch ₃ ch ₃ ^C 2 ^H 5 4 ch ₃ ch ₃ nC ₃ H ₇ 5 ch ₃ ch ₃ iC ₃ ^H 7 6 ch ₃ ch ₃ cyclopropyl 7 ch ₃ ch ₃ N-C ^ Hg 8 ch ₃ ch ₃ sC ₄ H ₉ 9 ch ₃ ch ₃ C ₄ H ₉ 10 ch ₃ ch ₃ t C ₄ H _g 11 ch ₃ ch ₃ ^n_C 5 ^H ll 12 ch ₃ ch ₃ i- ^C 5 ^H H 13 ch ₃ ch ₃ neo-C ^ Hj ^ 14 ch ₃ ch ₃ cyclopentyl 15 ch ₃ ch ₃ ^{n / a} 6 ^H 13 16 ch ₃ ch ₃ cyclohexyl 17 ch ₃ ch ₃ ^nC 8 ^H 17 18 ch ₃ ch ₃ ch ₂ ch ₂ ci 19 ch ₃ ch ₃ (ch ₂ ) ₄ ci 20 ch ₃ ch ₃ ch ₂ cn 21 ch ₃ ch ₃ ch ₂ ch ₂ cn 22 ch ₃ ch ₃ (ch ₂ ) ₃ cn 23 ch ₃ ch ₃ (ch ₂ ) ₄ cn 24 ch ₃ ch ₃ (ch ₂ ) ₆ cn 25 ch ₃ ch ₃ cyclohexylmethyl 26 ch ₃ ch ₃ Cyclohexylene-2-yl 27 ch ₃ ch ₃ cyclopropylmethyl 28 ch ₃ ch ₃ 2-cyclopropylene-l-yl 29 ch ₃ ch ₃ 2methoxyeth-yl 30 ch ₃ ch ₃ Ethoxyeth-2-yl 31 ch ₃ ch ₃ 2-Izopropoxyet-yl 32 ch ₃ ch ₃ 3-methoxypropyl-l-yl 33 ch ₃ ch ₃ 3-ethoxypropyl-yl 34 ch ₃ ch ₃ Izopropoxyprop 3-yl

R ³ R ⁴ R ^{5 CH} 3 ^CH 3 4-methoxybut-l-yl ch ₃ ch ₃ 4-1z Opropoxybut-1-yl ch ₃ ch ₃ Propen-3-yl ch ₃ ch ₃ But-2-en-l-yl ch ₃ ch ₃ 3-Methyl-but-2-en-l-yl ch ₃ ch ₃ 2-Vinyloxyet-yl ch ₃ ch ₃ Alyloxyet-yl ch ₃ ch ₃ 2-Trifluórmetoxyet-yl ch ₃ ch ₃ Trifluórmetoxyprop 3-yl ch ₃ ^CH 3 Difluórmetoxybut 4-yl ch ₃ ch ₃ Hydroxycarbonylmethyl ch ₃ ch ₃ methoxycarbonylmethyl ch ₃ ch ₃ aminocarbonylmethyl ch ₃ ch ₃ N-methylaminocarbonylmethyl ch ₃ ch ₃ N, N-dimethylaminocarbonyl-methyl ch ₃ ch ₃ 2-Hydroxykarbonylet-yl ch ₃ ch ₃ 2-methoxycarbonyleth-yl ch ₃ ch ₃ 2-Aminokarbonylet-yl ^CH 3 ch ₃ 2-N-Metylaminokarbonylet-yl ch ₃ ch ₃ 2-Dimetylaminokarbonylet-yl ch ₃ ch ₃ 2-aminoethyl-l-yl ch ₃ ch ₃ 2-amino-prop-l-yl ch ₃ ch ₃ 4-amino-but-l-yl ch ₃ ch ₃ 3-Dimethylamino-l-yl ch ₃ ch ₃ Aminotiokarbonylbut 4-yl ch ₃ ch ₃ 2-oxo-propyl ch ₃ ch ₃ cyclohexyl ch ₃ ch ₃ cyclopropyl ch ₃ ch ₃ cyclopentyl ch ₃ ch ₃ 2-Metoxyiminoprop-yl ch ₃ ch ₃ 2-Methoxyiminoeth-yl ch ₃ ch ₃ 6-Aminokarbonylhex-yl ch ₃ ch ₃ Aminotiokarbonylprop 3-yl ch ₃ ch ₃ 2-Aminotiokarbonylet-yl ch ₃ ch ₃ Aminotiokarbonylmetyl ch ₃ ch ₃ 4- (N, N-Dimethylamino) but-l-yl

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 2- (Methylthio) eth-l-yl ch ₃ ch ₃ 2- (methylsulfonyl) eth-l-yl ch ₃ ch ₃ 4- (Methylthio) prop-l-yl ch ₃ ch ₃ 4- (methylsulfonyl) prop-l-yl ch ₃ ch ₃ benzyl ch ₃ ch ₃ 2-FC ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-FC ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-F- ^c 6 H ₄ ^-CH 2 ch ₃ ch ₃ 2,3-F ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,4-F ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,5-F ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,6-F ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 3,4-F ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 3,5-F ₂ ^-C 6 ^H 3 ^-CH 2 ch ₃ ch ₃ 2-Cl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-Cl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 4-Cl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 2,3-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ ^CH 3 2,4-C 1 -C ₂ -C ₆ ^{hours 3-chloro} 2 ch ₃ ch ₃ 2,5-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,6-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ ^3, 4-Cl ₂ C ₆ H ₃ CH ₂ ch ₃ ch ₃ 3,5-Cl ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,3,4-Cl ₃ -C ₆ H ₂ -CH ₂ ch ₃ ch ₃ 2,3,5-Cl ₃ -C ₆ H ₂ -CH ₂ ch ₃ ch ₃ 2,3,6-Cl ₃ -C ₆ H ₂ -CH ₂ ch ₃ ch ₃ 2,4,5-Cl ₃ -C ₆ H ₂ -CH ₂ ch ₃ ch ₃ 2,4,6-Cl ₃ -C ₆ H ₂ -CH ₂ ch ₃ ch ₃ 3,4,5-Cl ₃ -C ₆ H ₂ -CH ₂ ch ₃ ch ₃ 2-Br-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-Br-C 8 H ₄ -CH ₂ ch ₃ ch ₃ 4-Br-C ₆ H ₄ CH ₂ ^CH 3 ch ₃ 2/3 “CH2 ch ₃ ch ₃ 2,4-Br ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,5-Br ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,6-Br ₂ -C ₈ H ₃ -CH ₂

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 3,4-Br ₂ - ^C 6 ^H 3 ^H 2-C ch ₃ ch ₃ 3,5-Br ₂ -C ₈ H ₃ -CH ₂ ch ₃ ch ₃ 2-F, 3-Cl-C ₆ H ₃ CH ₂ ch ₃ ^CH 3 2-F, 4-Cl-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 2-F, 5-Cl-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 2-F, 3-Br-C ₆ H ₃ CH ₂ ch ₃ ^CH 3 2-F, 4-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 2-F, 5-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 2-C1, 3-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 2-C1, 4-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 2-C1, 5-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 3-F, 4-Cl-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 3-F, 5-Cl-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 3-F, 6-Cl-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 3-F, 4-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 3-F, 5-Br-C 8 H ₃ -CH ₂ ch ₃ ch ₃ 3-F, 6-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 3-C1, 4-Br-C ₆ H ₃ CH ₂ ch ₃ ^CH 3 3-C1, _5-Br-3 CGH _CH2 ch ₃ ch ₃ 3-C1, 6-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 4-F, 5-Cl-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 4-F, _{6-Cl-3-CH 2} CGH ch ₃ ch ₃ 4-F, _5-Br-3 CGH _CH2 ch ₃ ch ₃ 4-F, 6-Br-C 8 H ₃ -CH ₂ ch ₃ ch ₃ 4-C1, 5-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 5-F, _{6-Cl-3-CH 2} CGH ch ₃ ch ₃ 5-F, 6-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 5-C1, 6-Br-C ₆ H ₃ CH ₂ ch ₃ ch ₃ 3-Br, 4-Cl, 5-Br-CgH ch ₃ ch ₃ 2-CN-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-CN-C 8 H ₄ -CH ₂ ch ₃ ch ₃ 4-CN-C 8 H ₄ -CH ₂ ch ₃ ch ₃ 2-NO ₂ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-NO ₂ -C ₈ H ₄ -CH ₂ ch ₃ ch ₃ 4-NO ₂ - ^C 6 ^H 4 - ^c H ₂ ch ₃ ch ₃ 2-CH ₃ -C ₈ H ₄ -CH ₂

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 3-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ ^4-CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,6- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ ^2-C 2 ^H 5 ^-C 6 ^H 4 ^-CH 2 ch ₃ ch ₃ ³ - ^C 2 ^H 5 - ^C 6 ^H 4 ' ^CH 2 ch ₃ ch ₃ ⁴ -C ₂ ^H 5 ^C 6 ^H 4 ^-CH 2 ch ₃ ch ₃ 2-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-C ₃ H ₇ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 2-cyclohexyl-C ₆ H ₄ -CH ch ₃ ch ₃ 3-cyclohexyl-C ₆ H ₄ -CH ch ₃ ch ₃ 4-cyclohexyl-C ₆ H ₄ -CH ch ₃ ch ₃ 2-Vinyl-C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-vinyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 4-Vinyl-C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 2-allyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-Allyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 4-Allyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ ^2-C 6 ^H 5 ^-C 6 ^H 4 ^-CH 2 ch ₃ ch ₃ ^3-C 6 ^H 5 ^-C 6 ^H 4 ^-CH 2 ch ₃ ch ₃ ⁴ - ^C 6 ^H 5 - ^C 6 ^H 4 ^CH 2 ch ₃ ch _{3 3-CH3,} 5-t C ₄ H _g C ₆ H ₃ - ch ₃ ch ₃ 2-OH-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-OH-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 4-OH-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 2-OCH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-OCH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-OCH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 2,3- (OCH 8) ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,4- (OCH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 2,5- (OCH ₃ ) ₂ -C ₆ H ₃ -CH ₂

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 3,4- (OCH ₃ ) ₂ -C ₆ H ₃ -CH ₂ ch ₃ ch ₃ 3,5- (OCH ₃ ) ₂ -C ₈ H ₃ -CH ₂ ch ₃ ch ₃ 3,4,5- (OCH ₃ ) ₃ -C ₆ H ₂ -CH ₂ ch ₃ ch ₃ 2-OC ₂ ^h 5- ^C 6 ^H 4 ^-CH 2 ch ₃ ch ₃ 3-OC ₂ H ₅ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-OC ₂ ^h 5- ^c 6 ^H 4 ^-CH 2 ch ₃ ch ₃ 2-O- (nC ₃ H ₇ ) -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-0- (n-C _{3 H?)} C ₆ H ₄ CH ₂ ch ₃ ch ₃ 4-0- (n-C _{3 H?)} C ₆ H ₄ CH ₂ ch ₃ ^CH 3 2-0- (i-C _{3 H?)} C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-O- (iC ₃ H ₇ ) -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-O- (1-C ₃ H ₇ ) -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-O- (nC ₄ H _g ) -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-O- (t C ₄ H ₉ ) -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-O- (nc ₆ H ₁₃ ) -c ₆ h ₄ -ch ₂ ch ₃ ^CH 3 2-0-allyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-O-allyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 4-Allyl-O-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 2- ^c F ₃ ^-C 6 ^H 4 ^-CH 2 ch ₃ ch ₃ 3-CF ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-CF ₃ ^-C 6 ^H 4 ^-CH 2 ch ₃ ch ₃ 2-Acetyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-Acetyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 4-Acetyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 2-Methoxycarbonyl-C 8 H ₄ -CH ₂ ch ₃ ch _{3 3-methoxycarbonyl-4-CH 2} CGH ch ₃ ch _{3 4-methoxycarbonyl-4-CH 2} CGH ch ₃ ch _{3 2-Aminocarbonyl-4 -CH2} CGH ch ₃ ch _{3 3-Aminocarbonyl-4 -CH2} CGH ch ₃ ^CH 3 _{4-Aminocarbonyl-4 -CH2} CGH ch ₃ ch ₃ 2-Dimethylaminocarbonyl-C 8 H ₄ -CH ₂ ch ₃ ch ₃ 3-Dimethylaminocarbonyl-C 8 H ₄ -CH ₂ ch ₃ ch ₃ 4-Dinetylaminokarbonyl _{CGH-4-CH 2} ch ₃ ch ₃ 2- (N-methylaminocarbonyl) -CgH _4-CH ch ₃ ch ₃ 3- (N-methylaminocarbonyl) -CgH _4-CH ch ₃ ch ₃ 4- (N-methylaminocarbonyl) -CgH _4-CH

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 2-H ₂ NC ₆ H ₄ -CH ₂ ch ₃ ^CH 3 ³ - ^H 2 ^N - ^C 6 ^H 4 ^CH 2 ch ₃ ch ₃ ^4- H ₂ ⁿ - ^C 6 ^H 4 ^-CH 2 ch ₃ ^CH 3 2-Aminothiocarbonyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-Aminothiocarbonyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 4-Aminothiocarbonyl-CGH ₄ -CH ₂ ch ₃ ch ₃ 2-methoxyimino-methyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-methoxyimino-methyl-C ₆ H ₄ CH ₂ ch ₃ ch _{3 4-methoxyiminomethyl-4 -CH2} CGH ch ₃ ch ₃ 2-formyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 3-Formyl-C 8 H ₄ -CH ₂ ch ₃ ch ₃ 4-formyl-C ₆ H ₄ CH ₂ ch ₃ ch ₃ 2- (1'-Methoxyiminoet-1'-yl) -C ₆ H ₄ -CH ch ₃ ch ₃ 3- (1'-Methoxyiminoet-1'-yl) -C ₈ H ₄ -CH ch ₃ ch ₃ 4- (1'-Methoxyiminoet-1'-yl) -C ₈ H ₄ -CH ^CH 3 ch ₃ 2-SCH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-SCH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-SCH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 2-SO ₂ CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-SO ₂ CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-SO ₂ CH ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 2-OCF ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-OCF ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-OCF ₃ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 2-OCHF ₂ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-OCHF ₂ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 4-OCHF ₂ -C ₆ H ₄ -CH ₂ ch ₃ ch ₃ 3-CF ₃ , 4-OCF ₃ -C ₆ H ₃ -CH ₂ ch ₃ ch _{3 1-Naphthyl-CH2} ch ₃ ch ₃ 2-Naphthyl-CH ₂ ch ₃ ch ₃ 2-fenoxyet-yl ch ₃ ch ₃ 2- (2-Chloro-phenoxy) eth-l-yl ch ₃ ch ₃ 2- (3'-Chloro-phenoxy) eth-l-yl ch ₃ ch ₃ 2- (4'-Chloro-phenoxy) eth-l-yl ch ₃ ch ₃ 2- (3 ', 5'-dichlorophenoxy) eth-l-yl ch ₃ ^CH 3 2- (2'-cyanophenoxy) eth-l-yl

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 2- (3'-cyanophenoxy) eth-l-yl ch ₃ ch ₃ 2- (4'-cyanophenoxy) eth-l-yl ch ₃ ch ₃ 2- (2'-methylphenoxy) eth-l-yl ch ₃ ch ₃ 2- (3'-methylphenoxy) eth-l-yl ch ₃ ch ₃ 2- (4'-methylphenoxy) eth-l-yl ch ₃ ch ₃ 2- (3'-tert-Butyl-phenoxy) eth-l-yl ch ₃ ch ₃ 2- (4'-tert-Butyl-phenoxy) eth-l-yl ch ₃ ch ₃ 2- (2'-nitrophenoxy) eth-l-yl ch ₃ ch ₃ 2- (3'-nitrophenoxy) eth-l-yl ch ₃ ch ₃ 2- (4'-nitrophenoxy) eth-l-yl ch ₃ ch ₃ 2- (2-methoxyphenoxy) eth-l-yl ch ₃ ch ₃ 2- (3'-methoxyphenoxy) eth-l-yl ch ₃ ch ₃ 2- (4'-methoxyphenoxy) eth-l-yl ch ₃ ch ₃ 2- (2'-trifluoromethylphenoxy) eth-l-yl ch ₃ ch ₃ 2- (3'-trifluoromethylphenoxy) eth-l-yl ch ₃ ch ₃ 2- (4'-trifluoromethylphenoxy) eth-l-yl ch ₃ ch ₃ 2- (2'-Acetylphenoxy) eth-l-yl ch ₃ ch ₃ 2- (3'-Acetylphenoxy) eth-l-yl ^CH 3 ^CH 3 2- (4'-Acetylphenoxy) eth-l-yl ch ₃ ch ₃ 2- (2'-methoxycarbonyl) eth-l-yl ch ₃ ch ₃ 2- (3'-methoxycarbonyl) eth-l-yl ch ₃ ch ₃ 2- (4'-methoxycarbonyl) eth-l-yl ch ₃ ch ₃ 2- (2'-dimethylaminocarbonyl) eth-l-yl ch ₃ ^CH 3 2- (3'-dimethylaminocarbonyl) eth-l-yl ch ₃ ch ₃ 2- (4'-dimethylaminocarbonyl) eth-l-yl ch ₃ ch ₃ 2- (2 ' Amintiokarbonyl) eth-l-yl ch ₃ ch ₃ 2- (3 ' Amintiokarbonyl) eth-l-yl ch ₃ ch ₃ 2- (4'-Amintiokarbonyl) eth-l-yl ch ₃ ch ₃ 2- (2'-methylsulfonyl) eth-l-yl ch ₃ ch ₃ 2- (3'-methylsulfonyl) eth-l-yl ch ₃ ch ₃ 2- (4'-methylsulfonyl) eth-l-yl ch ₃ ch ₃ Fenoxaprop-3-yl ch ₃ ch ₃ 3- (2-Chloro-phenoxy) -prop-l-yl ch ₃ ch ₃ 3- (3'-Chloro-phenoxy) -prop-l-yl ch ₃ ch ₃ 3- (4'-Chloro-phenoxy) -prop-l-yl ch ₃ ch ₃ 3- (3 ', 5', dichlorophenoxy) prop-l-yl

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 3- (2-cyanophenoxy) prop-l-yl ^CH 3 ch ₃ 3- (3'-cyanophenoxy) prop-l-y1 ch ₃ ch ₃ 3- (4 ' -cyanophenoxy) prop-1-yl ^CH 3 ch ₃ 3- (2-methylphenoxy) prop-l-yl ch ₃ ch ₃ 3- (3'-methylphenoxy) prop-l-yl ch ₃ ch ₃ 3- (4'-methylphenoxy) prop-l-yl ch ₃ ch ₃ 3- (2-methoxyphenoxy) prop-l-yl ch ₃ ch ₃ 3- (3'-methoxyphenoxy) prop-l-yl ch ₃ ch ₃ 3- (4'-methoxyphenoxy) prop-l-yl ch ₃ ch ₃ 3- (2-trifluoromethyl-phenoxy) -prop-l-yl ch ₃ ch ₃ 3- (3'-trifluoromethyl-phenoxy) -prop-l-yl ch ₃ ch ₃ 3- (4'-trifluoromethylphenoxy) prop-l-yl ch ₃ ch ₃ 4-phenoxybut-1-y1 ch ₃ ch ₃ 2-phenylethyl-yl ch ₃ ch ₃ 2- (2'-chlorophenyl) eth-l-yl ch ₃ ch ₃ 2- (3'-chlorophenyl) eth-l-yl ch ₃ ch ₃ 2- (4'-chlorophenyl) eth-l-yl ch ₃ ch ₃ 2- (3 ', 5'-Dichlorophenyl) et-1-yl ch ₃ ch ₃ 2- (2'-cyanophenyl) eth-l-yl ch ₃ ch ₃ 2- (3'-cyanophenyl) eth-l-yl ch ₃ ch ₃ 2- (4'-cyanophenyl) eth-l-yl ch ₃ ch ₃ 2- (2'-methylphenyl) eth-l-yl ch ₃ ch ₃ 2- (3'-methylphenyl) eth-l-yl ch ₃ ch ₃ 2- (4'-methylphenyl) eth-l-yl ch ₃ ch ₃ 2- (2'-Methoxyphenyl) eth-l-yl ch ₃ ch ₃ 2- (3'-Methoxyphenyl) eth-l-yl ^CH 3 ^CH 3 2- (4'-Methoxyphenyl) et-1-yl ch ₃ ch ₃ 2- (2'-trifluoromethylphenyl) eth-l-yl ch ₃ ch ₃ 2- (3'-trifluoromethylphenyl) eth-l-yl ch ₃ ch ₃ 2- (4'-trifluoromethylphenyl) eth-l-yl ch ₃ ch ₃ 3-phenyl-prop-l-yl ch ₃ ch ₃ 3- (2-chlorophenyl) prop-l-yl ch ₃ ch ₃ 3- (3'-chlorophenyl) prop-l-yl ch ₃ ch ₃ 3- (4'-Chlorophenyl) prop-l-yl ch ₃ ch ₃ 3- (2-cyanophenyl) -prop-l-yl ch ₃ ch ₃ 3- (3'-cyanophenyl) prop-l-yl

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 3- (4'-cyanophenyl) prop-l-yl ch ₃ ch ₃ 3- (2-trifluoromethylphenyl) prop-l-yl ch ₃ ch ₃ 4-phenyl-but-l-yl ch ₃ ch ₃ 4- (4'-chlorophenyl) but-l-yl ch ₃ ch ₃ 6- (4'-Chlorophenyl) hex-l-yl ch ₃ ch ₃ 2-pyridylmethyl ch ₃ ch ₃ 3-Pyridylmety1 ch ₃ ch ₃ 4-pyridylmethyl ch ₃ ch ₃ 4-Chloro-pyridin-2-ylmethyl ^CH 3 ch ₃ 5-Chloro-pyridin-2-ylmethyl ch ₃ ch ₃ 6-Chloro-pyridin-2-ylmethyl ch ₃ ch ₃ 5-Chlórpyridxn-3-ylmethyl ch ₃ ch ₃ 6-chloro-pyridin-3-ylmethyl ch ₃ ch ₃ 2-chloro-pyridin-4-ylmethyl ch ₃ ch ₃ 2-Pyrimidinylmethyl ch ₃ ^CH 3 4-chloro-pyrimidin-2-ylmethyl ch ₃ ch ₃ 5-Chloro-pyrimidin-2-ylmethyl ch ₃ ch ₃ 2-Chloro-pyrimidin-4-ylmethyl ch ₃ ch ₃ 6-Chloro-pyrimidin-4-ylmethyl ch ₃ ch ₃ 2-Chloro-pyrimidin-5-ylmethyl ch ₃ ch ₃ 4-pyridazinylmethyl ch ₃ ch ₃ 2-pyrazinylmethyl ch ₃ ch ₃ 5-chloropyrazine-2-ylmethyl ch ₃ ch ₃ 6-chloro-pyrazin-2-ylmethyl ch ₃ ch ₃ 3-pyridazinylmethyl ch ₃ ch ₃ 6-chloropyridazine-3-ylmethyl ch _{3 C} h ₃ 1,3,5-Triazinylmethyl ch ₃ ch ₃ 2-furylmethyl ch ₃ ch ₃ 3-furylmethyl ch ₃ ch ₃ 4-bromofuro-2-ylmety1 ch ₃ ch ₃ 5-chloro-furo-2-ylmethyl ch ₃ ch ₃ 2-thienylmethyl ch ₃ ch ₃ 3-thienylmethyl ch ₃ ch ₃ 5-methyl-thieno-3-ylmethyl ch ₃ ch ₃ 5-chloro-thienyl-2-ylmethyl ch ₃ ch ₃ 2-chloro-thienyl-4-ylmethyl

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 2-pyrrolylmethyl ch ₃ ch ₃ 3-Pyrolylnetyl ch ₃ ch ₃ 2oxazolylmethyl ch ₃ ch ₃ 4-Methyl-oxazol-2-ylmethyl ch ₃ ch ₃ 5-Methyl-oxazol-2-ylmethyl ch ₃ ch ₃ 4-chlorooxazole-2-ylmethyl ch ₃ ch ₃ 5-chlorooxazole-2-ylmethyl ch ₃ ch ₃ 4-oxazolylmethyl ch ₃ ch ₃ 2-Methyl-oxazol-4-ylmethyl ch ₃ ch ₃ 5-Methyl-oxazol-4-ylmethyl ch ₃ ch ₃ 2-chlorooxazole-4-ylinethyl ch ₃ ch ₃ 5-chlorooxazole-4-ylmethyl ch ₃ ch ₃ 5-oxazolylmethyl ch ₃ ch ₃ 2-Methyl-oxazol-5-ylmethyl CH ₃ ch ₃ 4-Methyl-oxazol-5-ylmethyl ch ₃ ch ₃ 2-chlorooxazole-5-ylmethyl ch ₃ ch ₃ 4-chlorooxazole-5-ylmethyl ch ₃ ch ₃ 2-thiazolylmethyl ch ₃ ch ₃ 4-Methyl-thiazol-2-ylmethyl ch ₃ ch ₃ 5-Methyl-thiazol-2-ylmethyl ch ₃ ch ₃ 4-chloro-thiazol-2-ylmethyl ch ₃ ch ₃ 5-chloro-thiazol-2-ylmethyl ch ₃ ch ₃ 4-thiazolylmethyl ch ₃ ch ₃ 2-Methyl-thiazol-4-ylmethyl ch ₃ ch ₃ 5-Methyl-thiazol-4-ylmethyl ch ₃ ch ₃ 2-chloro-thiazol-4-ylmethyl ch ₃ ch ₃ 5-chloro-thiazol-4-ylmethyl ch ₃ ch ₃ 5-thiazolylmethyl ch ₃ ch ₃ 2-Methyl-thiazol-5-ylmethyl ch ₃ ch ₃ 4-Methyl-thiazol-5-ylmethyl ch ₃ ch ₃ 2-chloro-thiazole-5-ylnetyl ch ₃ ch ₃ 4-Chloro-thiazol-5-ylmethyl ch ₃ ch ₃ 3-1zoxazolylmety1 ch ₃ ch ₃ 4-Methyl-oxazol-3-ylmethyl ch ₃ ch ₃ 5-Methyl-isoxazol-3-ylmethyl ch ₃ ch ₃ 4-Chloro-isoxazol-3-ylmethyl

No. R ³ R ⁴ R ⁵ 395 ch ₃ ch ₃ 5-Chloro-isoxazol-3-ylmethyl 396 ch ₃ ch ₃ 4-isoxazolylmethyl 397 ch ₃ ch ₃ 3-Methyl-isoxazol-4-ylmethyl 398 ch ₃ ch ₃ 5-Methyl-isoxazol-4-ylmethyl 399 ch ₃ ch ₃ 3-Chloro-isoxazol-4-ylmethyl 400 ch ₃ ch ₃ 5-Chloro-isoxazol-4-ylmethyl 401 ch ₃ ch ₃ 5-isoxazolylmethyl 402 ch ₃ ch ₃ 3-Methyl-isoxazol-5-ylmethyl 403 ch ₃ ch ₃ 4-Methyl-isoxazol-5-ylmethyl 404 ^CH 3 ch ₃ 3-Chloro-isoxazol-5-ylmethyl 405 ch ₃ ch ₃ 4-Chloro-isoxazol-5-ylmethyl 406 ch ₃ ch ₃ 3-isothiazolylmethyl 407 ch ₃ ch ₃ 4-methyl-isothiazole-3-ylmethyl 408 ch ₃ ch ₃ 5-methyl-isothiazole-3-ylmethyl 409 ch ₃ ch ₃ 4-Chlórizotiazol-3-ylmethyl 410 ^CH 3 ch ₃ 5-Chlórizotiazol-3-ylmethyl 411 ch ₃ ch ₃ 4-isothiazolylmethyl 412 ch ₃ ch ₃ 3-methyl-isothiazole-4-ylmethyl 413 ch ₃ ch ₃ 5-methyl-isothiazole-4-ylmethyl 414 ch ₃ ch ₃ 3-Chlórizotiazol-4-ylmethyl 415 ch ₃ ch ₃ 5-Chlórizotiazol-4-ylmethyl 416 ch ₃ ch ₃ 5-isothiazolylmethyl 417 ch ₃ ch ₃ 3-methyl-isothiazole-5-ylmethyl 418 ch ₃ ch ₃ 4-methyl-isothiazole-5-ylnetyl 419 ch ₃ ch ₃ 3-Chlórizotiazol-5-ylmethyl 420 ch ₃ ch ₃ 4-Chlórizotiazol-5-ylmethyl 421 ^CH 3 ch ₃ 4-ylmethyl 422 ch ₃ ch ₃ 1-phenyl-3-ylmethyl 423 ch ₃ ch ₃ l-methyl-imidazol-4-ylmethyl 424 ch ₃ ch ₃ 1-phenyl-1,2,4-triazol-3-ylmethyl 425 ch ₃ ch ₃ 1,2,4-oxadiazol-3-ylmethyl 426 ch ₃ ch ₃ 5-chloro-l, 2,4-oxadiazol-3-ylmethyl 427 ch ₃ ch ₃ 5-methyl-l, 2,4-oxadiazol-3-ylmethyl 428 ch ₃ ch ₃ 5-Trifluoromethyl-1,2,4-oxadiazol-3 ylmethyl 429 ch ₃ ch ₃ 1,3,4-oxadiazol-2-ylmethyl

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 5-chloro-l, 3,4-oxadiazol-2-ylmethyl ch ₃ ch ₃ 5-methyl-l, 3,4-oxadiazol-2-ylmethyl ch ₃ ch ₃ 5-Methoxy-l, 3,4-oxadiazol-2-ylmethyl ch ₃ ch ₃ 1,2,4-thiadiazol-3-ylmethyl ch ₃ ch ₃ 5-chloro-l, 2,4-thiadiazol-3-ylmethyl ch ₃ ch ₃ 5-methyl-l, 2,4-thiadiazol-3-ylmethyl ch ₃ ch ₃ 1,3,4-thiadiazol-2-ylmethyl ch ₃ ch ₃ 5-chloro-l, 3,4-thiadiazol-2-ylmethyl ch ₃ ch ₃ 5-methyl-l, 3,4-thiadiazol-2-ylmethyl ch ₃ ch ₃ 5-Cyano-l, 3,4-thiadiazol-2-ylmethyl ch ₃ ch ₃ 2- (2'-Pyridinyloxy) eth-l-yl ch ₃ ch ₃ 2- (3'-Pyridinyloxy) eth-l-yl ch ₃ ch ₃ 2- (4'-Pyridinyloxy) eth-l-yl ch ₃ ch ₃ 2- (2'-pyrimidinyloxy) eth-l-yl ch ₃ ch ₃ 2- (4'-pyrimidinyloxy) eth-l-yl ch ₃ ch ₃ 2- (5'-pyrimidinyloxy) eth-l-yl ch ₃ ch ₃ 2- (2'-pyrazinyloxy) eth-l-yl ch ₃ ch ₃ 2- (2'-pyridazinyloxy) eth-l-yl ch ₃ ch ₃ 2- (3'-pyridazinyloxy) eth-l-yl ch ₃ ch ₃ 2- (1 ', 3', 5'-Triazinyloxy) eth-l-yl ch ₃ ch ₃ 2- (5'-methylisoxazole-3'-yloxy) eth-l-yl ch ₃ ch ₃ 2- (5 ' Chloroisoxazole-3'-yloxy) eth-l-yl ch ₃ ch ₃ 2- (2'-Methoxythiazol-4'-yloxy) et-1-yl ch ₃ ch ₃ 2- (4'-chlorooxazole-2-yloxy) eth-l-yl ch ₃ ch ₃ 2- (1'-phenyl-1'H-1 ', 2', 4'-triazol-3'-yloxy) et-1-yl ch ₃ ch ₃ 2- (1'-phenyl-3'-yloxy) eth-l-yl ch ₃ ch ₃ ^C 6 ^H 5 ch ₃ ch ₃ 2-Cl-C ₆ H ₄ ^CH 3 ch ₃ 3-Cl-C ₆ H ₄ ch ₃ ch ₃ 4-Cl-C ₆ H ₄ ch ₃ ch ₃ 2,3-Cl ₂ -C ₆ H ₃ ch ₃ ch ₃ 2,4-Cl ₂ -C ₆ H ₃ ch ₃ ch ₃ 2,5-Cl ₂ -C ₆ H ₃ ch ₃ ch ₃ 3,4-Cl ₂ -C ₆ H ₃ ^CH 3 ^CH 3 3,5-Cl ₂ -C ₆ H ₃

R ³ R ⁴ R ⁵ ch ₃ ch ₃ 4-CN-C ₆ H ₄ ch ₃ ch ₃ 2-NO ₂ -C ₆ H ₄ ch ₃ ch ₃ 3-NO ₂ -C ₆ H ₄ ^CH 3 ch ₃ 4-NO ₂ -C ₆ H ₄ ch ₃ ch ₃ 2,4- (NO ₂ ) ₂ -C ₆ H ₃ ch ₃ ch ₃ 2-CH ₃ - ^c 6 ^H 4 ch ₃ ch ₃ 3-CH ₃ -C ₆ H ₄ ch ₃ ch ₃ 4-CH ₃ -C ₆ H ₄ ch ₃ ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ ch ₃ ^CH 3 2,4- (CH ₃ ) 2 ' ^c 6H ₃ ch ₃ ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ ch ₃ ch ₃ 2,6- (CH ₃ ) ₂ -C ₆ H ₃ ch ₃ ch ₃ ² - ^C 6 ^H 5 ^C 6 ^H 4 ch ₃ ch ₃ 3-C ₆ H ₅ -C ₆ H ₄ ch ₃ ch ₃ 4-C ₆ H ₅ -C ₆ H ₄ ch ₃ ch ₃ 3-OCH ₃ -C ₆ H ₄ ch ₃ ch ₃ 4-OCH ₃ -C ₆ H ₄ ch ₃ ch _{3 3-Acetyl-4} CGH ch ₃ ch _{3 4-Acetyl-4} CGH ch ₃ ch ₃ 3-Methoxycarbonyl-C ₆ H ₄ ch ₃ ch _{3 4-methoxycarbonyl-4} CGH ch ₃ ch ₃ 3-CF ₃ -C ₆ H ₄ ch ₃ ch ₃ 4-CF ₃ -C ₆ H ₄ ch ₃ ch ₃ 2-Naphthyl ch ₃ ch ₃ 6-chloropyridazine-3-yl ch ₃ ch ₃ 5-chloro-pyrazin-2-yl ch ₃ ch ₃ Quinolin-2-yl ch ₃ ch ₃ 2,5-Dimethylpyrazine-3-yl ch ₃ ch ₃ Pyrazin-2-yl ^CH 3 ^CH 3 3-chloropyrid-2-yl ch ₃ ch ₃ 6-chloropyrid-2-yl ch ₃ ch ₃ 4-Trifluoromethyl, 6-Chloropyrid ch ₃ ch ₃ 4-trifluoromethylpyrid-2-yl ch ₃ ch ₃ 6-trifluoromethylpyrid-2-yl ch ₃ ^CH 3 6-methoxy-pyridin-2-yl ch ₃ ^CH 3 5-chloropyrid-2-yl

R ³ R ⁴ R ⁵ ch ₃ ch ₃ Pyridin-2-yl ch ₃ ch ₃ Benzothiazol-2-yl ch ₃ ch ₃ 7-chloro-quinolin-4-yl ^CH 3 ch ₃ 3-nitro-pyridin-2-yl ch ₃ ch ₃ Pyrrol-3-yl ch ₃ ch ₃ Pyrrol-2-yl ch ₃ ch ₃ 2,6-Dioktylpyrid-4-yl ch ₃ ch ₃ 5-nitro-pyridin-2-yl ch ₃ ch ₃ Pyridin-4-yl ch ₃ ch ₃ Pyridin-3-yl ch ₃ ch ₃ Pyrimidin-2-yl ch ₃ ch ₃ Pyrimidin-4-yl ch ₃ ch ₃ Quinazolin-4-yl ch ₃ ch ₃ 6-Chloro-pyrimidin-4-yl ch ₃ ch ₃ 6-Methoxy-pyrimidin-4-yl ch ₃ ch ₃ 2,5,6-Trichlópyrimidín-4-yl ch ₃ ch ₃ 2,6-Dimethyl-pyrimidin-4-yl ch ₃ ch ₃ 2-Methyl, 6-Chloropyrimidin-4-yl ch ₃ ch ₃ 2-Methyl, 6-Ethoxy-pyrimidin-4-yl ch ₃ ch ₃ 4,5,6-trichloro-2-yl ch ₃ ch ₃ 4,6-dimethoxypyrimidin-2-yl ch ₃ ch ₃ 4,6-dimethyl-2-yl ch ₃ ch ₃ 4,6-Dichlórpyrinidín-2-yl ^CH 3 ch ₃ 4-Methyl, 6-methoxy-pyrimidin-2-yl ch ₃ ch ₃ 4-Chloro, 6-methoxy-pyrimidin-2-yl ch ₃ ch ₃ 6-Chloro-quinoxalin-2-yl ch ₃ ch ₃ 3,6-dichloro-1,2,4-triazin-5-yl ch ₃ ch ₃ 4-Methoxy-l, 3,5-triazin-2-yl ch ₃ ch ₃ 4-Ethoxy-l, 3,5-triazin-2-yl ch ₃ ch ₃ 4,6-dichloro-l, 3,5-triazin-2-yl ch ₃ ch ₃ 4-Ethoxy, 6-Chloro-1,3,5-triazin-2-yl ch ₃ ch ₃ Isoxazol-3-yl ch ₃ ch ₃ Thien-2-yl ch ₃ ch ₃ Fur-2-yl ch ₃ ch ₃ Tiatriazol-5-yl ch ₃ ch ₃ (E) -l-chloropropene-3-yl

R ³ R ⁴ R ⁵ ch ₃ ch ₃ (E) -4- (4'-Chlórpropeny1) but-2 ch ₃ ch ₃ Propyn-3-yl ch ₃ ch ₃ methylcarbonyl ch ₃ ch ₃ ethylcarbonyl ch ₃ ch ₃ n-propylcarbonyl ch ₃ ch ₃ i-propylcarbonyl ch ₃ ^CH 3 n-butylcarbonyl ch ₃ ch ₃ p-Butylcarbonyl ch ₃ ch ₃ i-Butylcarbonyl ch ₃ ch ₃ tbutyloxycarbonyl ch ₃ ch ₃ n-pentylcarbonyl ch ₃ ch ₃ i-Pentylkarbony1 ch ₃ ch ₃ neo-pentylcarbonyl ch ₃ ch ₃ n-hexylcarbonyl ch ₃ ch ₃ n-octylcarbonyl ch ₃ ^CH 3 1-propenylcarbonyl ch ₃ ch ₃ 2-penten-l-yl-carbonyl ch ₃ ch ₃ 2,5-heptadiene-yl-carbonyl ^CH 3 ^CH 3 benzoyl ch ₃ ch ₃ 2-chlorobenzoyl ch ₃ ch ₃ 3-chlorobenzoyl ch ₃ ch ₃ 4-chlorobenzoyl ch ₃ ch ₃ 2-cyanobenzoyl ch ₃ ^CH 3 3-cyanobenzoyl ch ₃ ch ₃ 4-cyanobenzoyl ch ₃ ch ₃ 4-methoxybenzoyl ch ₃ ch ₃ 2-Pyridylcarbonyl ch ₃ ch ₃ 3-Pyridylkarbony1 ch ₃ ch ₃ 4-Pyridylcarbonyl ch ₃ ch ₃ 2-pyrimidinylcarbonyl ch ₃ ch ₃ 2-0xazolylkarbonyl ch ₃ ch ₃ 4-Methyl-isoxazol-5-ylcarbonyl ch ₃ ch ₃ methylsulfonyl ch ₃ ch ₃ ethylsulfonyl ch ₃ ch ₃ n-propylsulfonyl ch ₃ ch ₃ i-propylsulfonyl

no. R ³ R ⁴ R ⁵ 573 ch ₃ ch ₃ n-butylsulfonyl 574 ch ₃ ch ₃ t-butylsulfonyl 575 ch ₃ ch ₃ n-pentylsulfonyl 576 ch ₃ ch ₃ neo-pentylsulfonyl 577 ch ₃ ch ₃ n-hexylsulfonyl 578 ch ₃ ch ₃ n-octylsulfonyl; 579 ch ₃ ch ₃ phenylsulfonyl 580 ch ₃ ch ₃ 2-chloro-phenylsulfonyl 581 ch ₃ ch ₃ 3-chloro-phenylsulfonyl 582 ch ₃ ch ₃ 4-Chlorophenylsulfonyl i 583 ch ₃ ch ₃ 2-cyanophenylsulfonyl 584 ch ₃ ch ₃ 3-cyanophenylsulfonyl 585 ch ₃ ch ₃ 4-cyanophenylsulfonyl 586 ch ₃ ch ₃ 2-Pyridylsulfonyl 587 ch ₃ ch ₃ 3-Pyridylsulfonyl 588 ch ₃ ch ₃ 4-Pyridylsulfonyl 589 ch ₃ ch ₃ 2-Pyrimidinylsulfonyl 590 ch ₃ ch ₃ 4-Oxazolylsulfonyl 591 ch ₃ ch ₃ 5-chloro-thiazol-2-yl-sulfonyl = 592 ch ₃ ch ₃ 2-C ₄ H _g -C ₆ H ₄ -CH ₂ 593 ch ₃ ch ₃ 3-C ₄ H _g -C ₆ H ₄ -CH ₂ * 594 ch ₃ ch ₃ 4-C ₄ H _g -C ₆ H ₄ -CH ₂ 595 ch ₃ ch ₃ 2- (4'-Chlorothiazol-2'-yloxy) et-1-yl 596 ch ₃ ch ₃ 2- (1 ^{1-methylpyrazole-4-yloxy)} eth-l-yl 597 ch ₃ ch ₃ 4-Br-C ₆ H ₄ 598 ch ₃ ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ 599 ch ₃ ch ₃ 4-C ₂ H ₅ -C ₆ H ₄ 600 ch ₃ ch ₃ 3-Dimethylaminocarbonyl-C ₆ H ₄ 601 ch ₃ ch ₃ 4-Dimethylaminocarbonyl-C ₆ H ₄ 602 ^CH 3 ch ₃ 2-hydroxy-prop-l-yl 603 ch ₃ ch ₃ 6-hydroxy-2-methyl-4-ylmethyl 604 ch ₃ ch ₃ [6-OH, 2-CH (CH ₃ ) ₂ -pyrimidin-4-yl] -CH ₂ 605 ch ₃ ch ₃ [6-OH, 2-CH (CH ₂₎ 2 ^- -amine; 4-yl] _-CH2 606 ch ₃ ch ₃ 5- (2'-furan) pent-l-yl 607 ch ₃ ch ₃ 5- (2'-N-methylpyrrole) pent-l-yl 608 ch ₃ ch ₃ [2- (4-Cl-C ₆ H ₄₎ -oxazole-4-yl] _-CH2

No. R ³ R ⁴ R ⁵ 609 ch ₃ ch ₃ 3-CF _3- pyridin-2-yl 610 ch ₃ ch ₃ 5-CF ₃ -pyridin-2-yl 611 ch ₃ ch ₃ 6- (2'Tienyl) hex-l-yl 612 ^CH 3 tC ₄ H ₉ H 613 ch ₃ tC ₄ H ₉ ch ₃ 614 ch ₃ tC ₄ H ₉ ^C 2 ^H 5 615 ch ₃ t C ₄ H _g nC ₃ H ₇ 616 ch ₃ t C ₄ H _g 1-C3H7 617 ch ₃ t C ₄ H _g cyclopropyl 618 ch ₃ t C ₄ H _g nC ₄ H ₉ 619 ch ₃ t-C ₄ Hg t C ₄ H _g 620 ch ₃ t C ₄ H _g ^nC 6 ^H 13 621 ch ₃ tC ₄ H ₉ (E) -l-chloropropene-3-yl 622 ch ₃ t ^- c ₄ h ₉ Propyn-3-yl 623 ch ₃ t C ₄ H _g 3-Methyl-but-2-en-l-yl 624 ^CH 3 t C ₄ H _g 2-Naphthyl-CH ₂ 625 ch ₃ t ~ C ₄ H ₉ 4-Cl-C ₆ H ₄ CH ₂ 626 ch ₃ tC ₄ H ₉ (E) -4- (4'-Chlorophenyl) but-2-en-l-yl 627 ch ₃ ^t ~ ^C 4 ^H 9 6- (4'-Chlorophenyl) hex-l-yl 628 ch ₃ t ^- C ₄ Hg 3-CF ₃ -C ₆ H ₄ 629 ch ₃ ^C 6 ^H 5 H 630 ch ₃ ^C 6 ^H 5 ch ₃ 631 ch ₃ ^C 6 ^H 5 ^C 2 ^H 5 632 ch ₃ ^C 6 ^H 5 nC ₃ H ₇ 633 ch ₃ ^C 6 ^H 5 i-CGH? 634 ch ₃ ^C 6 ^H 5 cyclopropyl 635 ch ₃ ^C 6 ^H 5 nC ₄ H ₉ 636 ch ₃ ^C 6 ^H 5 tC ₄ H ₉ 637 ch ₃ ^C 6 ^H 5 ^nC 6 ^H 13 638 ch ₃ ^C 6 ^H 5 4-Cl-C ₆ H ₄ CH ₂ 639 ch ₃ ^C 6 ^H 5 3-CF ₃ ^-C 6 H ₄ 640 ch ₃ ^C 6 ^H 5 6- (4'-Chlorophenyl) hex-l-yl 641 ch ₃ ^C 6 ^H 5 (E) -4- (4'-Chlorophenyl) but-2-en-l-yl 642 ch ₃ H H 643 ch ₃ H ch ₃ 644 ch ₃ H ^c 2 ^h 5

R ³ R ⁴ R ⁵ ch ₃ H nC ₃ H ch ₃ H t- ₃ h. ch ₃ OH H ch ₃ OH ch ₃ ch ₃ OH c ₂ h ₅ ch ₃ OH nC ₃ H ch ₃ OH iC ₃ H CH ₃ Cl ch ₃ ch ₃ Cl ^C 2 ^H 5 ch ₃ Cl n / a ₃ h, ch ₃ Cl I-C ₃ H. ch ₃ och ₃ H ch ₃ och ₃ ch ₃ ch ₃ och ₃ ^C 2 ^H 5 ch ₃ och ₃ nC ₃ H. ch ₃ och ₃ I-C ₃ H. ch ₃ sch ₃ H ch ₃ sch ₃ ch ₃ ch ₃ sch ₃ ^C 2 ^H 5 ch ₃ sch ₃ nC ₃ H. ch ₃ sch ₃ iC ₃ H. ch ₃ cyclopropyl H ch ₃ cyclopropyl ch ₃ ch ₃ cyclopropyl ^C 2 ^H 5 ch ₃ cyclopropyl n / a ₃ h. ch ₃ cyclopropyl t- ₃ h. ch ₃ 2-pyridyl H ch ₃ 2-pyridyl ch ₃ ch ₃ 2-pyridyl ^C 2 ^H 5 ^CH 3 2-pyridyl nC ₃ H- ch ₃ 2-pyridyl iC ₃ H. ch ₃ 3-pyridyl H ch ₃ 3-pyridyl ch ₃ ch ₃ 3-pyridyl ^C 2 ^H 5 ch ₃ 3-pyridyl nC ₃ H- ch ₃ 3-pyridyl I-C ₃ H-

R ³ R ⁴ R ⁵ ch ₃ 4-pyridyl H ch ₃ 4-pyridyl ch ₃ ch ₃ 4-pyridyl ^C 2 ^H 5 ch ₃ 4-pyridyl nC ₃ H ₇ ch ₃ 4-pyridyl 1-C3H7 ch ₃ 2-Pyridimidyl H ch ₃ 2-Pyridimidyl ch ₃ ch ₃ 2-Pyridimidyl ^C 2 ^H 5 ch ₃ 2-Pyridimidyl nC ₃ H ₇ ch ₃ 2-Pyridimidyl 1-C3H7 ch ₃ 4-Pyridimidyl H ch ₃ 4-Pyridimidyl ch ₃ ch ₃ 4-Pyridimidyl ^C 2 ^H 5 ch ₃ 4-Pyridimidyl nC ₃ H ₇ ch ₃ 4-Pyridimidyl 1-C3H7 ch ₃ 5-Pyridimidyl H ch ₃ 5-Pyridimidyl ch ₃ ch ₃ 5-Pyridimidyl ^C 2 ^H 5 ch ₃ 5-Pyridimidyl nC ₃ H ₇ ch ₃ 5-Pyridimidyl t-c ₃ h ₇ ch ₃ 1,3,5-triazinyl H ch ₃ 1,3,5-triazinyl ch ₃ ch ₃ 1,3,5-triazinyl ^C 2 ^H 5 ch ₃ 1,3,5-triazinyl nC ₃ H ₇ ch ₃ 1,3,5-triazinyl t-c ₃ h ₇ ch ₃ 2-furyl H ch ₃ 2-furyl ^CH 3 ch ₃ 2-furyl ^C 2 ^H 5 ch ₃ 2-furyl nC ₃ H ₇ ch ₃ 2-furyl i-C 3 H y ch ₃ 3-furyl H ch ₃ 3-furyl ^CH 3 ch ₃ 3-furyl ^C 2 ^H 5 ch ₃ 3-furyl nC ₃ H ₇ ch ₃ 3-furyl I-C3H7 ch ₃ 2-Thienyl H

R ³ R ⁴ R ⁵ ch ₃ 2-Thienyl ch ₃ ch ₃ 2-Thienyl ^C 2 ^H 5 ch ₃ 2-Thienyl nC ₃ H ₇ ch ₃ 2-Thienyl I-C3H7 ch ₃ 3-Thienyl H ch ₃ 3-Thienyl ch ₃ ch ₃ 3-Thienyl ^C 2 ^H 5 ch ₃ 3-Thienyl nC ₃ H ₇ ch ₃ 3-Thienyl 1-C3H7 ch ₃ 2-oxazolyl H ch ₃ 2-oxazolyl ch ₃ ch ₃ 2-oxazolyl 5 ', 2' ch ₃ 2-oxazolyl nC ₃ H ₇ ch ₃ 2-oxazolyl 1-C3H7 ch ₃ 4-oxazolyl H ch ₃ 4-oxazolyl ^CH 3 ch ₃ 4-oxazolyl ^C 2 ^H 5 ch ₃ 4-oxazolyl nC ₃ H ₇ ch ₃ 4-oxazolyl 1-C3H7 ch ₃ 2-Thiazolyl H ch ₃ 2-Thiazolyl ch ₃ ch ₃ 2-Thiazolyl ^C 2 ^H 5 ch ₃ 2-Thiazolyl nC ₃ H ₇ ch ₃ 2-Thiazolyl I-C3H7 ch ₃ 4-Thiazolyl H ch ₃ 4-Thiazolyl ch ₃ ch ₃ 4-Thiazolyl 5 ', 2' ch ₃ 4-Thiazolyl n-C 3 H 7 ch ₃ 4-Thiazolyl t-c ₃ h ₇ ch ₃ 3-isoxazolyl H ch ₃ 3-isoxazolyl ch ₃ ch ₃ 3-isoxazolyl ^C 2 ^H 5 ch ₃ 3-isoxazolyl nC ₃ H ₇ ch ₃ 3-isoxazolyl iC ₃ H ₇ ^CH 3 5-isoxazolyl H ch ₃ 5-isoxazolyl ch ₃

R ³ R ⁴ R ^{5 CH} 3 5-isoxazolyl ^C 2 ^H 5 ch ₃ 5-isoxazolyl nC ₃ Hy ch ₃ 5-isoxazolyl t-c ₃ h ₇ ^CH 3 2-imidazolyl H ch ₃ 2-imidazolyl ch ₃ ch ₃ 2-imidazolyl ^C 2 ^H 5 ch ₃ 2-imidazolyl nC ₃ H ₇ ch ₃ 2-imidazolyl i — c ₃ h ₇ ch ₃ 3-Pyrazolyl H ch ₃ 3-Pyrazolyl ch ₃ ch ₃ 3-Pyrazolyl ^C 2 ^H 5 ch ₃ 3-Pyrazolyl nC ₃ H ₇ ^CH 3 3-Pyrazolyl t-c ₃ h ₇ ch ₃ 4-Pyrazolyl H ch ₃ 4-Pyrazolyl ch ₃ ^CH 3 4-Pyrazolyl ^C 2 ^H 5 ch ₃ 4-Pyrazolyl nC ₃ H ₇ ch ₃ 4-Pyrazolyl 1-C3H7 och ₃ H H och ₃ H ch ₃ och ₃ H ^C 2 ^H 5 och ₃ H nC ₃ H ₇ och ₃ H ³ - ^- C ₃ H ₇ och ₃ OH H och ₃ OH ch ₃ och ₃ OH c ₂ h ₅ och ₃ OH nC ₃ H ₇ och ₃ OH iC3H7 och ₃ Cl ^nC 4 ^H 9 och ₃ Cl ch ₃ och ₃ Cl c ₂ h ₅ och ₃ Cl nC ₃ H ₇ och ₃ Cl I-C3H7 och ₃ och ₃ H och ₃ och ₃ ch ₃ och ₃ och ₃ ^C 2 ^H 5

R ³ R ⁴ R ⁵ och ₃ och ₃ nC ₃ H ₇ och ₃ och ₃ t-c ₃ h ₇ och ₃ sch ₃ H och ₃ sch ₃ ch ₃ och ₃ sch ₃ ^C 2 ^H 5 och ₃ sch ₃ ^nC 3 ^H 7 och ₃ sch ₃ t-c ₃ h ₇ och ₃ ch ₃ H och ₃ ch ₃ ch ₃ och ₃ ch ₃ ^C 2 ^H 5 och ₃ ch ₃ nC ₃ H ₇ och ₃ ch ₃ 1-C3H7 och ₃ cyclopropyl H och ₃ cyclopropyl ch ₃ och ₃ cyclopropyl ^C 2 ^H 5 och ₃ cyclopropyl nC ₃ H ₇ och ₃ cyclopropyl 1-C3H7 och ₃ 2-pyridyl H och ₃ 2-pyridyl ch ₃ och ₃ 2-pyridyl ^C 2 ^H 5 och ₃ 2-pyridyl nC ₃ H ₇ och ₃ 2-pyridyl 1-C3H7 och ₃ 3-pyridyl H och ₃ 3-pyridyl ch ₃ och ₃ 3-pyridyl ^C 2 ^H 5 och ₃ 3-pyridyl ⁿ ' ^C 3 ^H 7 och ₃ 3-pyridyl C ₃ H ₇ och ₃ 4-pyridyl H och ₃ 4-pyridyl ch ₃ OCH ₃ 4-pyridyl ^C 2 ^H 5 och ₃ 4-pyridyl nC ₃ H ₇ och ₃ 4-pyridyl 1-C3H7 och ₃ 2-pyrimidyl H och ₃ 2-pyrimidyl ch ₃ och ₃ 2-pyrimidyl ^C 2 ^H 5 och ₃ 2-pyrimidyl nC ₃ H ₇

R ³ R ⁴ R ⁵ och ₃ 2-pyrimidyl 1-C3H7 och ₃ 4-pyrimidyl H och ₃ 4-pyrimidyl ch ₃ och ₃ 4-pyrimidyl ^C 2 ^H 5 och ₃ 4-pyrimidyl nC ₃ H ₇ och ₃ 4-pyrimidyl I-C3H7 och ₃ 5-pyrimidyl H och ₃ 5-pyrimidyl ch ₃ och ₃ 5-pyrimidyl ^C 2 ^H 5 och ₃ 5-pyrimidyl nC ₃ H ₇ och ₃ 5-pyrimidyl CI-C ₃ H ₇ och ₃ 1,3,5-triazinyl H och ₃ 1,3,5-triazinyl ch ₃ och ₃ 1,3,5-triazinyl ^C 2 ^H 5 och ₃ 1,3,5-triazinyl och ₃ 1,3,5-triazinyl iC ₃ H ₇ och ₃ 2-Fúry1 H och ₃ 2-Fúry1 ch ₃ och ₃ 2-Fúry1 ^C 2 ^H 5 och ₃ 2-Fúry1 Γΐ ^- ΟβΗγ och ₃ 2-furyl CI-C ₃ H ₇ och ₃ 3-furyl H och ₃ 3-Fúry1 ch ₃ och ₃ 3-furyl ^C 2 ^H 5 och ₃ 3-Fúry1 nC ₃ H ₇ och ₃ 3-furyl 1-C3H7 och ₃ 2-Thienyl H och ₃ 2-Thienyl ch ₃ och ₃ 2-Thienyl ^C 2 ^H 5 och ₃ 2-Thienyl nC ₃ H ₇ och ₃ 2-Thienyl 1-C3H7 och ₃ 3-Thienyl H och ₃ 3-Thienyl ch ₃ och ₃ 3-Thienyl ^C 2 ^H 5 och ₃ 3-Thienyl nC ₃ H ₇ och ₃ 3-Thienyl i- ^c 3H ₇

R ³ R ⁴ R ⁵ och ₃ 2-oxazolyl H och ₃ 2-oxazolyl ch ₃ och ₃ 2-oxazolyl ^C 2 ^H 5 och ₃ 2-oxazolyl nC ₃ H och ₃ 2-oxazolyl IC ₃ H och ₃ 4-oxazolyl H och ₃ 4-oxazolyl ch ₃ och ₃ 4-oxazolyl ^C 2 ^H 5 och ₃ 4-oxazolyl nC ₃ H och ₃ 4-oxazolyl I-C ₃ H och ₃ 2-Thiazolyl H och ₃ 2-Thiazolyl ch ₃ och ₃ 2-Thiazolyl ^C 2 ^H 5 och ₃ 2-Thiazolyl nC ₃ H. och ₃ 2-Thiazolyl t-c ₃ h, och ₃ 4-Thiazolyl H och ₃ 4-Thiazolyl ch ₃ och ₃ 4-Thiazolyl ^C 2 ^H 5 och ₃ 4-Thiazolyl nC ₃ H och ₃ 4-Thiazolyl iC ₃ H och ₃ 3-isoxazolyl H och ₃ 3-isoxazolyl ch ₃ och ₃ 3-isoxazolyl ^C 2 ^H 5 och ₃ 3-isoxazolyl nC ₃ H, och ₃ 3-isoxazolyl t- ₃ h. och ₃ 5-isoxazolyl H och ₃ 5-isoxazolyl ch ₃ och ₃ 5-isoxazolyl ^C 2 ^H 5 och ₃ 5-isoxazolyl nC ₃ H och ₃ 5-isoxazolyl I-C ₃ H. och ₃ 2-imidazolyl H och ₃ 2-imidazolyl ch ₃ och ₃ 2-imidazolyl ^C 2 ^H 5 och ₃ 2-imidazolyl nC ₃ H · och ₃ 2-imidazolyl t- ₃ h. och ₃ 3-Pyrazolyl H

R ³ R ⁴ R ⁵ och ₃ 3-Pyrazolyl ch ₃ och ₃ 3-Pyrazolyl ^C 2 ^H 5 och ₃ 3-Pyrazolyl n-C 3 γγ och ₃ 3-Pyrazolyl 1-C3H7 och ₃ 4-Pyrazolyl H och ₃ 4-Pyrazolyl ch ₃ och ₃ 4-Pyrazolyl ^C 2 ^H 5 och ₃ 4-Pyrazolyl n-C3H'7 och ₃ 4-Pyrazolyl ^ '^ 3 ^ 7 OH H H OH H ch ₃ OH H ^C 2 ^H 5 OH H nC ₃ H ₇ OH H 1-C3H7 OH OH H OH OH ch ₃ OH OH ^C 2 ^H 5 OH OH nC ₃ H ₇ OH OH 1-C3H7 OH C1 Π ^- C ^ Hg OH C1 CH ₃ OH C1 ^C 2 ^H 5 OH C1 nC ₃ H ₇ OH Cl CI-C ₃ H ₇ OH och ₃ H OH och ₃ ch ₃ OH och ₃ ^C 2 ^H 5 OH och ₃ nC ₃ H ₇ OH och ₃ 1-C3H7 OH sch ₃ H OH sch ₃ ch ₃ OH sch ₃ ^C 2 ^H 5 OH sch ₃ OH sch ₃ t-c ₃ h ₇ OH ch ₃ H OH ch ₃ ch ₃

R ³ R ⁴ R ⁵ OH ch ₃ ^C 2 ^H 5 OH ch ₃ nC ₃ H OH ch ₃ t- ₃ h OH cyclopropyl H OH cyclopropyl ch ₃ OH cyclopropyl ^C 2 ^H 5 OH cyclopropyl nC ₃ H OH cyclopropyl t- ₃ h OH 2-pyridyl H OH 2-pyridyl ch ₃ OH 2-pyridyl ^C 2 ^H 5 OH 2-pyridyl nC ₃ H · OH 2-pyridyl t- ₃ h · OH 3-pyridyl H OH 3-pyridyl ch ₃ OH 3-pyridyl ^C 2 ^H 5 OH 3-pyridyl nC ₃ H OH 3-pyridyl iC ₃ H. OH 4-pyridyl H OH 4-pyridyl ch ₃ OH 4-pyridyl ^C 2 ^H 5 OH 4-pyridyl nC ₃ H · OH 4-pyridyl I-C ₃ H, OH 2-pyrimidyl H OH 2-pyrimidyl ch ₃ OH 2-pyrimidyl ^C 2 ^H 5 OH 2-pyrimidyl nC ₃ H · OH 2-pyrimidyl t- ₃ h. OH 4-pyrimidyl H OH 4-pyrimidyl ch ₃ OH 4-pyrimidyl ^C 2 ^H 5 OH 4-pyrimidyl nC ₃ H. OH 4-pyrimidyl t- ₃ h. OH 5-pyrimidyl H OH 5-pyrimidyl ch ₃ OH 5-pyrimidyl c ₂ h ₅

R ³ R ⁴ R ⁵ OH 5-pyrimidyl n-C β Ηγ OH 5-pyrimidyl I-C3H7 OH 1,3,5-triazinyl H OH 1,3,5-triazinyl ch ₃ OH 1,3,5-triazinyl ^C 2 ^H 5 OH 1,3,5-triazinyl nC ₃ Hy OH 1,3,5-triazinyl 1-C3H7 OH 2-furyl H OH 2-Fúry1 ch ₃ OH 2-furyl ^C 2 ^H 5 OH 2-furyl nC ₃ H ₇ OH 2-furyl I-C3H7 OH 3-Fúry1 H OH 3-furyl ch ₃ OH 3-furyl ^C 2 ^H 5 OH 3-Fúry1 nC ₃ H ₇ OH 3-furyl iC ₃ H ₇ OH 2-Thienyl H OH 2-Thienyl ch ₃ OH 2-Thienyl ^C 2 ^H 5 OH 2-Thienyl nC ₃ H ₇ OH 2-Thienyl I-C3H7 OH 3-Thienyl H OH 3-Thienyl ch ₃ OH 3-Thienyl ^C 2 ^H 5 OH 3-Thienyl nC ₃ H ₇ OH 3-Thienyl iC ₃ H ₇ OH 2-oxazolyl H OH 2-oxazolyl ch ₃ OH 2-oxazolyl ^C 2 ^H 5 OH 2-oxazolyl OH 2-oxazolyl iC ₃ H ₇ OH 4-oxazolyl H OH 4-oxazolyl ch ₃ OH 4-oxazolyl ^C 2 ^H 5 OH 4-oxazolyl

no. R ³ R ⁴ R ⁵ 1005 OH 4-oxazolyl iC ₃ H ₇ 1006 OH 2-Thiazolyl H 1007 OH 2-Thiazolyl ch ₃ 1008 OH 2-Thiazolyl ^C 2 ^H 5 1009 OH 2-Thiazolyl n-C ^ H y 1010 OH 2-Thiazolyl 1-C3H7 1011 OH 4-Thiazolyl H 1012 OH 4-Thiazolyl ch ₃ 1013 OH 4-Thiazolyl ^C 2 ^H 5 1014 OH 4-isoxazolyl 1015 OH 4-isoxazolyl i — C ₃ H ₇ 1016 OH 3-isoxazolyl H 1017 OH 3-isoxazolyl ch ₃ 1018 OH 3-isoxazolyl ^C 2 ^H 5 1019 OH 3-isoxazolyl nC ₃ H ₇ 1020 OH 3-isoxazolyl i ^-C 3 ^H 7 1021 OH 5-isoxazolyl H 1022 OH 5-isoxazolyl ch ₃ 1023 OH 5-isoxazolyl ^C 2 ^H 5 1024 OH 5-isoxazolyl nC ₃ H ₇ 1025 OH 5-isoxazolyl 1-C3H7 1026 OH 2-imidazolyl H 1027 OH 2-imidazolyl ch ₃ 1028 OH 2-imidazolyl ^C 2 ^H 5 1029 OH 2-Imidazolyl η-ΟβΗγ 1030 OH 2-imidazolyl 1-C3H7 1031 OH 3-Pyrazolyl H 1032 OH 3-Pyrazolyl ch ₃ 1033 OH 3-Pyrazolyl ^C 2 ^H 5 1034 OH 3-Pyrazolyl 1035 OH 3-Pyrazolyl 1-C3H7 1036 OH 4-Pyrazolyl H 1037 OH 4-Pyrazolyl ch ₃ 1038 OH 4-Pyrazolyl ^C 2 ^H 5 1039 OH 4-Pyrazolyl nC ₃ H ₇ 1040 OH 4-Pyrazolyl 1-C3H7

R ³ R ⁴ R ⁵ H H H H H ch ₃ H H ^C 2 ^H 5 H H nC ₃ H ₇ H H I-C3H7 H OH H H OH ch ₃ H OH ^C 2 ^H 5 H OH nC ₃ H ₇ H OH I-C3H7 H Cl N-C ^ Jhg H Cl ch ₃ H Cl ^C 2 ^H 5 H Cl nC ₃ Hy H Cl 1-C3H7 H OCH ₃ H H och ₃ ch ₃ H och ₃ ^C 2 ^H 5 H och ₃ nC ₃ H ₇ H och ₃ 1-C3H7 H ch ₃ H H ch ₃ ch ₃ H ch ₃ ^C 2 ^H 5 H ^CH 3 n CgHy H ch ₃ I-C3H7 H cyclopropyl H H cyclopropyl ch ₃ H cyclopropyl ^C 2 ^H 5 H cyclopropyl nC ₃ H ₇ H cyclopropyl t-c ₃ h ₇ Cl H H Cl H ch ₃ Cl H ^C 2 ^H 5 Cl H nC ₃ H ₇ Cl H 1-C3H7 Cl OH H

R ³ R ⁴ R ⁵ Cl OH ch ₃ C1 OH ^C 2 ^H 5 Cl OH nC ₃ H ₇ C1 OH C ₃ H 7 Cl Cl N-C ^ Hg C1 Cl CH ₃ C1 Cl ^C 2 ^H 5 Cl Cl C1 Cl I-C3H7 C1 och ₃ H Cl och ₃ ch ₃ C1 och ₃ ^C 2 ^H 5 Cl och ₃ nC ₃ H ₇ C1 och ₃ 1-C3H7 Cl ch ₃ H Cl ch ₃ ch ₃ C1 ch ₃ ^C 2 ^H 5 Cl ch ₃ nC ₃ H ₇ Cl ^CH 3 I-C3H7 Cl cyclopropyl H Cl cyclopropyl ch ₃ Cl cyclopropyl c ₂ h ₅ Cl cyclopropyl nC ₃ H ₇ Cl cyclopropyl 1-C3H7 sch ₃ H H sch ₃ H ch ₃ sch ₃ H ^C 2 ^H 5 sch ₃ H nC ₃ H ₇ sch ₃ H iC ₃ H ₇ sch ₃ OH H sch ₃ OH ch ₃ sch ₃ OH ^C 2 ^H 5 sch ₃ OH nC ₃ H ₇ sch ₃ OH 1-C3H7 sch ₃ ch ₃ H sch ₃ ch ₃ ch ₃

R ³ R ⁴ R ⁵ sch ₃ ch ₃ ^C 2 ^H 5 sch ₃ ^CH 3 nC ₃ H ₇ sch ₃ ch ₃ I-C3H7 sch ₃ sch ₃ H sch ₃ sch ₃ ch ₃ sch ₃ sch ₃ ^C 2 ^H 5 sch ₃ sch ₃ nC ₃ H ₇ sch ₃ sch ₃ ^X- ^ 3 ^ 7 sch ₃ cyclopropyl H sch ₃ cyclopropyl ch ₃ sch ₃ cyclopropyl ^C 2 ^H 5 sch ₃ cyclopropyl nC ₃ H ₇ sch ₃ cyclopropyl I-C3H7 cyclopropyl H H cyclopropyl H ch ₃ cyclopropyl H ^C 2 ^H 5 cyclopropyl H nC ₃ H ₇ cyclopropyl H 1-C3H7 cyclopropyl OH H cyclopropyl OH ch ₃ cyclopropyl OH ^C 2 ^H 5 cyclopropyl OH nC ₃ H ₇ cyclopropyl OH i-C-yokes cyclopropyl C1 n ^- C ^Hg cyclopropyl C1 ch ₃ cyclopropyl C1 ^C 2 ^H 5 cyclopropyl C1 nC ₃ H ₇ cyclopropyl C1 CGH-i-yl cyclopropyl OCH ₃ H cyclopropyl och ₃ ch ₃ cyclopropyl och ₃ ^C 2 ^H 5 cyclopropyl och ₃ nC ₃ H ₇ cyclopropyl och ₃ 1-C3H7 cyclopropyl sch ₃ H cyclopropyl sch ₃ ch ₃ cyclopropyl sch ₃ ^C 2 ^H 5

R ³ R ⁴ R ⁵ cyclopropyl sch ₃ nC ₃ H ₇ cyclopropyl sch ₃ 1-C3H7 cyclopropyl ch ₃ H cyclopropyl ch ₃ ch ₃ cyclopropyl ch ₃ ^C 2 ^H 5 cyclopropyl ch ₃ nC ₃ H ₇ cyclopropyl ch ₃ 1-C3H7 ch ₃ 2-FC ₆ H ₄ H ch ₃ 2-FC ₆ H ₄ ch ₃ ch ₃ 2-FC ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-F- ^C 6 ^H 4 nC ₃ H ₇ ch ₃ 2-FC ₆ ^H 4 1-C3H7 ch ₃ 2-FC ₆ H ₄ n ~ C ₄ Hg ch ₃ 2-F- ^C 6 ^H 4 t C ₄ H _g ch ₃ 2-FC ₆ ^H 4 ⁿ ' ^C 6 ^H 13 ch ₃ ² - ^{F C} 6 ^H 4 Prop-en-3-yl ch ₃ 2-FC ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-FC ₆ ^H 4 Propyn-3-yl ch ₃ 2-F- ^C 6 ^H 4 3-methyl-but-2-en-l-yl ch ₃ 3-FC ₆ H ₄ H ^CH 3 3-FC ₆ H ₄ ch ₃ ch ₃ 3-FC ₆ H ₄ ^C 2 ^H 5 ch ₃ 3-FC ₆ H ₄ nC ₃ H ₇ ch ₃ 3-FC ₆ H ₄ I-C3H7 ch ₃ 3-FC ₆ ^H 4 Π — C ₄ Hg ch ₃ 3-FC ₆ H ₄ t C ₄ H _g ch ₃ 3-FC ₆ ^H 4 ^nC 6 ^H 13 ch ₃ 3-FC ₆ ^H 4 Prop-en-3-y1 ch ₃ ³ -F- ^C 6 ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-FC ₆ H ₄ Propyn-3-yl ch ₃ ³ -FC ₆ ^H 4 3-methyl-but-2-en-l-yl ch ₃ ⁴ -FC ₆ ^H 4 H ch ₃ 4-FC ₆ H ₃ ch ₃ ch ₃ ⁴ -F-C6 ^h 4 ^C 2 ^H 5 ch ₃ ⁴ -FC ₆ ^H 4 nC ₃ H ₇ ch ₃ ⁴ -F-C6 ^h 4 1-C3H7

R ³ R ⁴ R ⁵ ch ₃ ⁴ -fc ₆ h ₄ n ^- C ₄ H ₉ ch ₃ 4-FC ₆ ^H 3 t C ₄ H _g ch ₃ 4-FC ₆ H ₃ ^{n = C} 6 ^H ₃ ch ₃ 4-FC ₆ ^H 3 Prop-en-3-yl ch ₃ 4-FC ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ ⁴ -FC ₆ ^H 4 Propyn-3-yl ch ₃ 4-FC ₆ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 2-Cl-C ₆ H ₄ H ch ₃ 2-Cl-C ₆ H ₄ ch ₃ ch ₃ 2-Cl-C ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-Cl-C ₆ H ₄ nC ₃ Hy ch ₃ 2-Cl-C ₆ H ₄ iC ₃ H? ch ₃ 2-C 1-C ₆ H ₄ nC ₄ Hg ch ₃ 2-Cl-C ₆ H ₄ t C ₄ H _g ch ₃ 2-Cl-C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 2-Cl-C ₆ H ₄ Prop-en-3-yl ch ₃ 2-Cl-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-Cl-C ₆ H ₄ Propyn-3-yl ch ₃ 2-Cl-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-Cl-C ₆ H ₄ H ch ₃ 3-Cl-C ₆ H ₄ ch ₃ ch ₃ 3-Cl-C ₆ H ₄ ^c 2 ^h 5 ch ₃ 3-Cl-C ₆ H ₄ nC ₃ H ₇ ch ₃ 3-Cl-C ₆ H ₄ t-c ₃ h ₇ ch ₃ 3-Cl-C ₆ H ₄ n ^- C ₄ H ₉ ch ₃ 3-Cl-C ₆ H ₄ tC ₄ H ₉ ch ₃ 3-Cl-C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 3-Cl-C ₆ H ₄ Prop-en-3-yl ch ₃ 3-Cl-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-Cl-C ₆ H ₄ Propyn-3-yl ch ₃ 3-Cl-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-Cl-C ₆ H ₄ H ch ₃ 4-C1-C ₆ H ₄ ch ₃ ch ₃ 4-Cl-C ₆ H ₄ 5 ', 2' ch ₃ 4-Cl-C ₆ H ₄ nC ₃ H ₇ ch ₃ 4-Cl-C ₆ H ₄ 1-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4-Cl-C ₆ H ₄ nC ₄ Hg ch ₃ 4-Cl-C ₆ H ₄ tC ₄ H ₉ ch ₃ 4-Cl-C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 4-Cl-C ₆ H ₄ Prop-en-3-yl ch ₃ 4-Cl-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-Cl-C ₆ H ₄ Propyn-3-yl ch ₃ 4-Cl-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2,3-Cl ₂ -C ₆ H ₃ H ch ₃ 2,3-Cl _{2-CGH 3} ch ₃ ch ₃ 2,3-Cl ₂ -C ₆ H ₃ ^C 2 ^H 5 ch ₃ 2,3-Cl _{2-CGH 3} nC ₃ H ₇ ch ₃ 2,3-Cl ₂ -C ₆ H ₃ 1-C3H7 ch ₃ 2,3-Cl ₂ -C ₆ H ₃ nC ₄ Hg ch ₃ 2,3-Cl ₂ -C ₆ H ₃ tC ₄ H ₉ ch ₃ 2,3-Cl ₂ -C ₆ H ₃ n-CGH ^ ch ₃ 2,3-Cl ₂ -C ₆ H ₃ Prop-en-3-yl ch ₃ 2,3-Cl ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2,3-Cl ₂ -C ₆ H ₃ Propyn-3-yl ch ₃ 2,3-Cl ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 2,4-Cl ₂ -C ₆ H ₃ H ch ₃ 2,4-Cl ₂ -C ₆ H ₃ ch ₃ ch ₃ 2,4-Cl _{2-CGH 3} ^C 2 ^H 5 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ n-C ch ₃ 2,4-Cl ₂ -C ₆ H ₃ I-C3H7 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ nC ₄ Hg ch ₃ 2,4-Cl ₂ -C ₆ H ₃ tC ₄ H ₉ ch ₃ 2,4-Cl ₂ -C ₆ H ₃ nC ₆ ^H 13 ch ₃ 2,4-Cl ₂ -C ₆ H ₃ Prop-en-3-yl ch ₃ 2,4-Cl ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2,4-Cl ₂ -C ₆ H ₃ Propyn-3-yl ch ₃ 2,4-Cl ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 2,5-Cl ₂ -C ₆ H ₃ H ch ₃ 2,5-Cl ₂ -C ₆ H ₃ ch ₃ ch ₃ 2,5-Cl ₂ -C ₆ H ₃ ^C 2 ^H 5 ch ₃ 2,5-Cl ₂ -C ₆ H ₃ nC ₃ H ₇ ch ₃ 2,5-Cl ₂ -C ₆ H ₃ I-C3H7

R ³ R ⁴ R ⁵ ch ₃ 2,5-Cl ₂ -C ₆ H ₃ nC ₄ H _g ch ₃ 2,5-Cl ₂ -C ₆ H ₃ tC ₄ H ₉ ch ₃ 2,5-Cl ₂ -C ₆ H ₃ ^nC 6 ^H 13 ch ₃ 2,5-Cl ₂ -C ₆ H ₃ Prop-en-3-yl ch ₃ 2,5-Cl ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2,5-Cl ₂ -C ₆ H ₃ Propyn-3-yl ch ₃ 2,5-Cl ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 2,6-Cl ₂ -C ₆ H ₃ H ch ₃ 2,6-Cl ₂ -C ₆ ^h 3 ch ₃ ch ₃ 2 _/ 6-Cl ₂ -C ₆ H ₃ ^C 2 ^H 5 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ ^n_C 3 ^H 7 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ 1-C3H7 ch ₃ 2,6-Cl ₂ -C ₆ H ₃ nC ₄ H ₉ ch ₃ 2,6-Cl ₂ -C ₆ H ₃ t C ₄ H _g ch ₃ 2,6-Cl ₂ -C ₆ H ₃ ^nC 6 ^H 13 ch ₃ 2,6-Cl ₂ -C ₆ ^H 3 Prop-en-3-yl ch ₃ 2,6-Cl ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2,6-Cl ₂ -C ₆ H ₃ Propyn-3-yl ch ₃ 2,6-Cl ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 3,4-Cl ₂ -C ₆ H ₃ H ch ₃ 3,4-Cl ₂ -C ₆ H ₃ ch ₃ ch ₃ 3,4-Cl ₂ -C ₆ H ₃ ^C 2 ^H 5 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ ^n_C 3 ^H 7 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ iC ₃ H ₇ ch ₃ 3,4-Cl ₂ -C ₆ H ₃ nC ₄ H ₉ ch ₃ 3,4-Cl ₂ -C ₆ H ₃ t C ₄ H _g ^CH 3 ^3,4 -C 1 ₂ -C ₆ ^h 3 ^nC 6 ^H 13 ch ₃ 3,4-Cl ₂ -C ₆ H ₃ Prop-en-3-yl ch ₃ 3,4-Cl ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3,4-Cl ₂ -C ₆ H ₃ Propyn-3-yl ch ₃ 3,4-Cl ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl ^CH 3 3,5-Cl ₂ -C ₆ H ₃ H ch ₃ 3,5-Cl ₂ -C ₆ H ₃ ch ₃ ch ₃ 3,5-Cl ₂ -C ₈ H ₃ ^C 2 ^H 5 ch ₃ ³ ' ^5-C 12 ^-C 6 ^H 3 11-C3H7 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ CI-C ₃ H ₇

No R ³ R ⁴ R ⁵ 1293 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ nC ₄ Hg 1294 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ tC ₄ H ₉ 1295 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ ^nC 6 ^H 13 1296 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ Prop-en-3-yl 1297 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl 1298 ch ₃ 3 _of 5-Cl ₂ -C ₆ H ₃ Propyn-3-yl 1299 ch ₃ 3,5-Cl ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl 1300 ch ₃ 2-Br-C ₆ H ₄ H 1301 ch ₃ 2-Br-C ₆ H ₄ ch ₃ 1302 ch ₃ 2-Br-C ₆ H ₄ ^C 2 ^H 5 1303 ch ₃ 2-Br-C ₆ H ₄ nC ₃ H ₇ 1304 ch ₃ 2-Br-C ₆ H ₄ i- ^C 3 ^H 7 1305 ch ₃ 2-Br-C ₆ H ₄ nC ₄ H _g 1306 ch ₃ 2-Br-C ₆ H ₄ t C ₄ H _g 1307 ch ₃ 2-Br-C ₆ H ₄ ^nC 6 ^H 13 1308 ^CH 3 2-Br-C ₆ H ₄ Prop-en-3-yl 1309 ch ₃ 2-Br-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl 1310 ch ₃ 2-Br-C ₆ H ₄ Propyn-3-yl 1311 ch ₃ 2-Br-C ₆ H ₄ 3-methyl-but-2-en-l-yl 1312 ch ₃ 3-Br_C ₆ H ₄ H 1313 ch ₃ 3-Br-C ₆ H ₄ ch ₃ 1314 ch ₃ 3-Br-C ₆ H ₄ ^C 2 ^H 5 1315 ch ₃ 3-Br-C ₆ H ₄ n-C H-j 1316 ch ₃ 3-Br-C ₆ H ₄ t-c ₃ h ₇ 1317 ch ₃ 3-Br-C ₆ H ₄ nC ₄ H ₉ 1318 ch ₃ 3-Br-C ₆ H ₄ tC ₄ H ₉ 1319 ch ₃ 3-Br-C ₆ H ₄ ^nC 6 ^H 13 1320 ch ₃ 3-Br-C ₆ H ₄ Prop-en-3-yl 1321 ch ₃ 3-Br-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl 1322 ch ₃ 3-Br-C ₆ H ₄ Propyn-3-yl 1323 ch ₃ 3-Br-C ₆ H ₄ 3-methyl-but-2-en-l-yl 1324 ch ₃ 4-Br-C ₆ H ₄ H 1325 ch ₃ 4-Br- _Cg H ₄ ch ₃ 1326 ch ₃ 4-Br-C ₆ H ₄ ^c 2 ^H 5 1327 ch ₃ 4-Br-C ₆ H ₄ nC ₃ H ₇ 1328 ch ₃ 4-Br-C ₆ H ₄ I-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4-Br-C ₆ H ₄ nC ₄ Hg ch ₃ 4-Br-C ₆ H ₄ tC ₄ H ₉ ch ₃ 4-Br-C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 4-Br-C ₆ H ₄ Prop-en-3-yl ch ₃ 4-Br-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-Br-C ₆ H ₄ Propyn-3-yl ch ₃ 4-Br-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-IC ₆ H ₄ H ch ₃ 2-IC ₆ ^H 4 ch ₃ ch ₃ 2-IC ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-IC ₆ H ₄ nC ₃ H ₇ ch ₃ 2-IC ₆ H ₄ I-C3H7 ch ₃ 2-IC ₆ H ₄ nC ₄ H ₉ ch ₃ 2-IC ₆ H ₄ tC ₄ H ₉ ch ₃ 2-IC ₆ H ₄ ^nC 6 ^H 13 ch ₃ ^2-IC 6 ^H 4 Prop-en-3-yl ch ₃ 2-IC ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-IC ₆ H ₄ Propyn-3-yl ^CH 3 2-IC ₆ H ₄ 3-methyl-but-2-en-l-yl ^CH 3 3-IC ₆ H ₄ H ch ₃ S-I-C ^ ch ₃ ch ₃ 3-IC ₆ H ₄ ^C 2 ^H 5 ch ₃ 3-IC ₆ H ₄ nC ₃ H ₇ ch ₃ 3-I _4-CGH I-C3H7 ch ₃ 3-IC ₆ ^H 4 n — C ₄ H ₉ ch ₃ 3-IC ₆ H ₄ t C ₄ H _g ch ₃ 3-IC ₆ H ₄ ^n_C 6 ^H 13 ch ₃ ³ -Ι-Ο _θ ^Η 4 Prop-en-3-yl ch ₃ ³ -I- ^C 6 ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-IC ₆ ^H 4 Propyn-3-yl ch ₃ ³ - ₆ h ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-IC ₆ H ₄ H ch ₃ ⁴ -I ^C 6 ^H 4 ch ₃ ch ₃ 4-IC ₆ H ₄ ^C 2 ^H 5 ch ₃ ⁴ -I ^C 6 ^H 4 nC ₃ H ₇ ^CH 3 4-IC ₆ H ₄ I-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4-IC ₆ H ₄ nC ₄ H _g ch ₃ ⁴ -I- ^C 6 ^H 4 tC ₄ H ₉ ch ₃ 4-IC ₆ H ₄ ^nC 6 ^H 13 ch ₃ ⁴ -I- ^c 6 ^H 4 Prop-en-3-yl ch ₃ ⁴ 'IC ₆ ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ ⁴ -I- ^C 6 ^H 4 Propyn-3-yl ch ₃ ⁴ -ic ₆ hrs ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-CN-C ₆ H ₄ H ch ₃ 2-CN-C ₆ H ₄ ch ₃ ch ₃ 2-CN-C ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-CN-C ₆ H ₄ nC ₃ H ₇ ch ₃ 2-CN-C ₆ H ₄ iC ₃ H ₇ ch ₃ 2-CN-C ₆ H ₄ n ⁼ C ₄ H _g ch ₃ 2-CN-C ₆ H ₄ t C ₄ H _g ch ₃ 2-CN-C ₆ H ₄ ^nC 6 ^H 13 ^CH 3 2-CN-C ₆ H ₄ Prop-en-3-yl ch ₃ 2-CN-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-CN-C ₆ H ₄ Propyn-3-yl ch ₃ 2-CN-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-CN-C ₆ H ₄ H ch ₃ 3-CN-C ₆ H ₄ ch ₃ ch ₃ 3-CN-C ₆ H ₄ ^C 2 ^H 5 ch ₃ 3-CN-C ₆ H ₄ nC ₃ H ₇ ^CH 3 3-CN-C ₆ H ₄ I-C3H7 ch ₃ 3-CN-C ₆ H ₄ nC ₄ H ₉ ch ₃ 3-CN-C ₆ H ₄ t ~ C ₄ H ₉ ch ₃ 3-CN-C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 3-CN-C ₆ H ₄ Prop-en-3-yl ch ₃ 3-CN-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-CN-C ₆ H ₄ Propyn-3-yl ch ₃ 3-CN-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-CN-C ₆ H ₄ H ch ₃ 4-CN-C ₆ H ₄ ch ₃ ch ₃ 4-CN-C ₆ H ₄ ^c 2 ^H 5 ch ₃ 4-CN-C ₆ H ₄ nC ₃ H ₇ ch ₃ 4-CN-C ₆ H ₄ I-C ₃ ^h 7

R ³ R ⁴ R ⁵ ch ₃ 4-CN-C ₆ H ₄ nC ₄ Hg ch ₃ 4-CN-C ₆ H ₄ t C ₄ H _g ch ₃ 4-CN-C ₆ H ₄ ^n_C 6 ^H 13 ch ₃ 4-CN-C ₆ H ₄ Prop-en-3-yl ch ₃ 4-CN-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-CN-C ₆ H ₄ Propyn-3-yl ch ₃ 4-CN-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-NO ₂ -C ₆ H ₄ H ch ₃ 2-NO ₂ -C ₆ H ₄ ch ₃ ch ₃ 2-NO ₂ -C ₆ H ₄ 5 ', 2' ch ₃ 2-NO ₂ -C ₆ H ₄ ^nC 3 ^H 7 ch ₃ 2-NO ₂ -C ₆ H ₄ I-C3IÍ7 ch ₃ 2-NO ₂ -C ₆ H ₄ nC ₄ Hg ch ₃ 2-NO ₂ -C ₆ H ₄ tC ₄ H ₉ ch ₃ 2-NO ₂ -C ₆ H ₄ ⁿ ~ ^C 6 ^H 13 ch ₃ 2-NO ₂ ^-C 6 ^H 4 Prop-en-3-yl ch ₃ 2-NO ₂ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-NO ₂ -C ₆ H ₄ Propyn-3-yl ch ₃ 2 - NO ₂ - ^c 6 ^H 4 3-methyl-but-2-en-l-yl ch ₃ 3-NO ₂ -C ₆ H ₄ H ch ₃ 3-NO ₂ -C ₆ H ₄ ch ₃ ch ₃ 3-NO ₂ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 3-NO ₂ -C ₆ H ₄ ch ₃ 3-NO ₂ ^-C 6 ^H 4 iC ₃ H ₇ ch ₃ 3-NO ₂ -C ₆ H ₄ nC ₄ H ₉ ch ₃ 3-NO ₂ ^-C 6 ^H 4 tC ₄ H ₉ ch ₃ 3-NO ₂ -C ₆ H ₄ nC ₆ ^H 3 ch ₃ 3-NO ₂ -C ₆ H ₄ Prop-en-3-yl ch ₃ 3-NO ₂ ^-C 6 ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-NO ₂ -C ₆ H ₄ Propyn-3-yl ch ₃ 3-NO ₂ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-no ₂ -c ₆ h ₄ H ch ₃ 4-no ₂ -c ₆ h ₄ ch ₃ ch ₃ ⁴ - ^NO 2 - ^C 6 ^H 4 ^C 2 ^H 5 ch ₃ 4-NO ₂ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 4-NO ₂ ^-C 6 ^H 4 iC ₃ H ₇

R ³ R ⁴ R ⁵ ch ₃ 4-NO ₂ -C ₆ H ₄ nC ₄ Hg ch ₃ 4-NO ₂ ^-C 6 ^H 4 tC ₄ H ₉ ch ₃ 4-NO ₂ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 4-HO ₂ -C ₆ H ₄ Prop-en-3-yl ch ₃ 4-NO ₂ ^-C 6 ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-NO ₂ ^-C 6 ^H 4 Propyn-3-yl ^CH 3 4-NO ₂ ^-C 6 ^H 4 3-methyl-but-2-en-l-yl ch ₃ 2-CH ₃ -C ₆ H ₄ H ch ₃ 2-CH ₃ -C ₆ H ₄ ch ₃ ^CIÍ 3 2-CH ₃ -C ₆ H ₄ ^C 2 «5 ch ₃ 2-CH ₃ -C ₆ H ₄ nc ₃ H ₇ ch ₃ 2- ^CH 3 ^C 6 ^H 4 1-C3H7 ch ₃ 2-CH ₃ -C ₆ H ₄ nC ₄ H ₉ ch ₃ 2-CH ₃ - ^c 6 ^H 4 t-C ₄ Hg ch ₃ 2-CH ₃ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 2-CH ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 2-CH ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-CH ₃ -C ₆ H ₄ Propyn-3-yl ch ₃ 2-CH ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-CH ₃ -C ₆ H ₄ H ch ₃ 3-CH ₃ -C ₆ H ₄ ch ₃ ^CH 3 3-CH ₃ - ^c 6 ^H 4 ^C 2 ^H 5 ch ₃ 3-CH ₃ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 3-CH ₃ - ^c 6 H ₄ 1-C3H7 ch ₃ 3-CH ₃ - ^c 6 ^H 4 Π — C ₄ Hg ch ₃ 3-CH ₃ - ^c 6 H ₄ tC ₄ Hg ch ₃ ³ -CH ₃ ^-C 6 ^H 4 ^nC 6 ^H 13 ch ₃ ³ -CH ₃ - ^c 6 ^H 4 Prop-en-3-yl ch ₃ 3-CH ₃ ^-C 6 ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-CH ₃ ^-C 6 ^H 4 Propyn-3-yl ch ₃ ³ -CH ₃ ^-C 6 ^H 4 3-methyl-but-2-en-l-yl ch ₃ 4-CH ₃ ^-C 6 ^H 4 H ch ₃ 4-CH ₃ -C ₆ H ₄ ch ₃ ch ₃ 4-CH ₃ ^-C 6 ^H 4 ^C 2 ^H 5 ch ₃ 4-CH ₃ - ^c 6 ^H 4 n-C β Ηγ ch ₃ 4-CH ₃ -C ₆ H ₄ 1-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4-CH ₃ ^-C 6 ^H 4 n — C ₄ Hg ch ₃ 4-CH ₃ ^-C 6 ^H 4 tC ₄ Hg ch ₃ 4-CH ₃ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 4-CH ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 4-CH ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-CH ₃ ^-C 6 ^H 4 Propyn-3-yl ch ₃ 4-CH ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ H ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ ch ₃ ch ₃ 2,3- (CH ₃ ) ₂ C ₆ H ₃ ^C 2 ^H 5 ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ nC ₃ H ₇ ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ t-c ₃ h ₇ ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ nC ₄ H _g ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ t C ₄ H _g ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ ^nC 6 ^H 13 ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ Prop-en-3-yl ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2,3- (CH ₃ ) ₂ -C ₆ H ₃ Propyn-3-yl ch ₃ 2,3- (CH ₃ ) ₂ 'C ₆ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ H ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ ch ₃ ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ ^C 2 ^H 5 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ nC ₃ H ₇ ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ I-C3H7 ch ₃ 2,4- (CH ₃ ) ₂ C ₆ H ₃ nC ₄ H _g ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ tC ₄ H ₉ ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ ^nC 6 ^H 13 ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ Prop-en-3-yl ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ Propyn-3-yl ch ₃ 2,4- (CH ₃ ) ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 2,5- (CH ₃ ) ₂ -C ₈ H ₃ H ch ₃ 2,5- (CH ₃ ) ₂ -C ₈ H ₃ ch ₃ ch ₃ 2,5- (CH ₃ ) ₂ -C ₈ H ₃ ^C 2 ^H 5 ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ nC ₃ H ₇ ch ₃ 2,5- (CH ₃ ) ₂ -C ₈ H ₃ ί-ΟβΗγ

R ³ R ⁴ R ⁵ ch ₃ 2,5- (CH ₃ ) 2 -C ₈ H ₃ N-C ^ Hg ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ tC ₄ H ₉ ch ₃ 2,5- (CH ₃ ) 2 ^c 6 H ₃ ⁿ ' ^C 6 ^H 13 ch ₃ 2,5- (CH ₃ ) ₂ -C ₈ H ₃ Prop-en-3-yl ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2,5- (CH ₃ ) ₂ -C ₈ H ₃ Propyn-3-yl ch ₃ 2,5- (CH ₃ ) ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 2,6- (CH ₃ ) ₂ -C ₈ H ₃ H ch ₃ 2,6- (CH ₃ ) ₂ -C ₈ H ₃ ch ₃ ch ₃ 2,6- (CH ₃ ) ₂ -C ₆ H ₃ ^C 2 ^H 5 ch ₃ 2,6- (CH ₃ ) ₂ -C ₈ H ₃ ΓΙ ^- ch ₃ 2,6- (CH ₃ ) ₂ -C ₆ H ₃ t-c ₃ h ₇ ch ₃ 2,6- (CH ₃ ) ₂ C ₈ H ₃ n ⁼ C ₄ Hg ch ₃ 2,6- (CH ₃ ) ₂ -C ₆ H ₃ tC ₄ H ₉ ch ₃ 2,6- (CH ₃ ) ₂ -C ₆ H ₃ ^nC 6 ^H 13 ch ₃ 2,6- (CH ₃ ) ₂ -C ₈ H ₃ Prop-en-3-yl ch ₃ 2,6- (CH ₃ ) ₂ -C ₈ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2,6- (CH ₃ ) ₂ -C ₆ H ₃ Propyn-3-yl ch ₃ 2,6- (CH ₃ ) ₂ -C ₈ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ H ^CH 3 3,4- (CH ₃ ) ₂ -C ₈ H ₃ ch ₃ ch ₃ 3,4- (CH ₃ ) ₂ -C ₈ H ₃ ^C 2 ^H 5 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ nC ₃ H ₇ ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ I-C3H7 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ nC ₄ H ₉ ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ tC ₄ H ₉ ^GH 3 3,4- (CH ₃ ) ₂ -C ₈ H ₃ ^{n C} 6 ^H 13 ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ Prop-en-3-yl ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ Propyn-3-yl ch ₃ 3,4- (CH ₃ ) ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl ch ₃ 3,5- (CH ₃ ) ₂ -C ₈ H ₃ H ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ ch ₃ ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ ^C 2 ^H 5 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ ⁿ ' ^C 3 ^H 7 ch ₃ 3,5- (CH ₃ ) ₂ -C ₈ H ₃ t-c ₃ h ₇

No R ³ R ⁴ R ⁵ 1545 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ nC ₄ Hg 1546 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ tC ₄ H ₉ 1547 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ ^{n C} 6 ^H 13 1548 ch ₃ 3,5- _{(CH3) 2} ^_ ₃ CGH Prop-en-3-yl 1549 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ (E) -l-chloro-prop-l-en-3-yl 1550 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ Propyn-3-yl 1551 ch ₃ 3,5- (CH ₃ ) ₂ -C ₆ H ₃ 3-methyl-but-2-en-l-yl 1552 ch ₃ 2- ^C 2 ^H 5 - ^C 6 ^H 4 H 1553 ch ₃ 2-C ₂ H ₅ -C ₆ H ₄ ch ₃ 1554 ch ₃ 2-C ₂ H ₅ -C ₆ H ₄ ^C 2 ^H 5 1555 ch ₃ 2 ^- C ₂ Hg-CGH ₄ nC ₃ H ₇ 1556 ch ₃ 2 ^- C2H5-C6H4 1-C3H7 1557 ch ₃ 2 ^ 2 ^ 5 ^^ ^ 6 4 n ⁼ C ₄ Hg 1558 ch ₃ 2 ^ 2 ^ 5 ^ 6 ^ 4 tC ₄ H ₉ 1559 ch ₃ 2 “ ^C 2 ^H 5“ ^C 6 ^H 4 ^{n C} 6 ^H 13 1560 ch ₃ 2 ', 2', 5 ^ 6 ^ 4 Prop-en-3-yl 1561 ch ₃ 2-C ₂ H ₅ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl 1562 ch ₃ 2-C ₂ Hg-CGH ₄ Propyn-3-yl 1563 ch ₃ 2-C ₂ H ₅ -C ₆ H ₄ 3-methyl-but-2-en-l-yl 1564 ch ₃ 3-C ₂ H ₅ -C ₆ H ₄ H 1565 ch ₃ 3-C ₂ H ₅ -C ₆ H ₄ ch ₃ 1566 ch ₃ ^3-C 2 ^H 5 ^C 6 ^H 4 ^C 2 ^H 5 1567 ch ₃ 3-C ₂ H ₅ -C ₆ H ₄ nC ₃ H ₇ 1568 ch ₃ 3-C ₂ H ₅ -C ₆ H ₄ iC ₃ H ₇ 1569 ch ₃ ^3_ ^ 2 ^ 5- ^ 6 ^ 4 n ^- C ^Hg 1570 ch ₃ ^{3 C} 2 ^H 5 - ^C 6 ^H 4 tC ₄ Hg 1571 ch ₃ 3-C ₂ H ₅ -C ₆ H ₄ ⁿ ' ^C 6 ^H 13 1572 ^CH 3 ^3_ C2 ^ 5-- ^ 6 ^ 4 Prop-en-3-yl 1573 ch ₃ 3-C ₂ H ₅ -C ₆ H ₄ (E) -1-Chloroprop-1-en-3-yl 1574 ch ₃ 3-C ₂ H ₅ -C ₆ H ₄ Propyn-3-yl 1575 ch ₃ 3-C ₂ H ₅ -C ₆ H ₄ 3-methyl-but-2-en-l-yl 1576 ch ₃ ^{4 C} 2 ^H 5 6 ^H 4 ^_C H 1577 ch ₃ 4-C ₂ H ₅ -C ₆ H ₄ ch ₃ 1578 ch ₃ 4-C ₂ H ₅ -C ₆ H ₄ ^C 2 ^H 5 1579 ch ₃ ⁴ - ^ '2 ^ 5 ^- ^' 6 ^ 4 nC ₃ H ₇ 1580 ch ₃ 4-C ₂ H ₅ -C ₆ H ₄ 1-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4 ^- C 2 ^- C 8 H 4 n ~ C ₄ Hg ch ₃ ⁴ ~ ^ 2 ^ 5 - ^ - 5 ^ 4 tC ₄ Hg ch ₃ 4-C ₂ H ₅ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 4-C ₂ ^H 5 - ^C 6 ^H 4 Prop-en-3-yl ch ₃ ^4- ^ 2 ^ 5- ^ 6 ^ 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-C ₂ H ₅ -C ₆ H ₄ Propyn-3-yl ^CH 3 4-C ₂ H 5 -C ₆ ^H 4 3-methyl-but-2-en-l-yl ch ₃ 2-C ₃ H ₇ -C ₆ H ₄ H ch ₃ 2-IC ₃ ^H 7- ^C 6 ^H 4 ch ₃ ch ₃ 2-C ₃ H ₇ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-C ₃ H _? -C ₆ H ₄ nC ₃ H ₇ ch ₃ 2-C ₃ H ₇ -C ₆ H ₄ iC ₃ H ₇ ch ₃ 2-C ₃ H ₇ -C ₆ H ₄ nC ₄ Hg ch ₃ 2-C ₃ ^H 7- ^C 6 ^H 4 t C ₄ H _g ch ₃ 2-C ₃ H ₇ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 2'-C ₃ H ₇ -C ₈ H ₄ Prop-en-3-yl ch ₃ 2-C ₃ H ₇ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-C ₃ H ₇ -C ₆ H ₄ Propyn-3-yl ^CH 3 2-C ₃ H ₇ -C ₈ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ H ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ ch ₃ ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 3-iC ₃ H _7, -C ₄ H _g i-CSH? ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ nC ₄ Hg ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ tC ₄ Hg ch ₃ 3-i-C ₃ H _7, -C ₄ H _g n- ^c 6 ^H 13 ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ Prop-en-3-yl ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ Propyn-3-yl ch ₃ 3-C ₃ H ₇ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-C ₃ H ₇ -C ₆ H ₄ H ch ₃ 4-C ₃ H ₇ -C ₆ H ₄ ch ₃ ch ₃ ^{4 -} i ^- C ₃ H ₇ ^- C ₈ H ₈ ^{- C} 2 ^H 5 ch ₃ 4-C ₃ H ₇ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 4-C ₃ H ₇ -C ₈ H ₄ I-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4 &lt; 1 ^& gt ^{; -} c3H7-cgH4 nC ₄ Hg ch ₃ 4-C ₃ H ₇ -C ₆ H ₄ t ~ C ₄ H _g ch ₃ 4-C ₃ H ₇ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ ^{4- C} 3 ^H 7 ^-C 6 ^H 4 Prop-en-3-yl ch ₃ 4 ^- i ^- C3H7-CGH ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-C ₃ H ₇ -C ₆ H ₄ Propyn-3-yl ch ₃ 4-C ₃ H ₇ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-OH-C ₆ H ₄ H ch ₃ 2-OH-C ₆ H ₄ ch ₃ ch ₃ 2-OH-C ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-OH-C ₆ H ₄ nC ₃ H ₇ ch ₃ 2-OH-C ₆ H ₄ 1-C3H7 ^CH 3 2-OH-C ₆ H ₄ nC ₄ Hg ch ₃ 2-OH-C ₆ H ₄ t ~ C ₄ Hg ch ₃ 2-OH-C ₆ H ₄ ⁿ ~ ^C 6 ^H 13 ch ₃ 2-OH-C ₆ H ₄ Prop-en-3-yl ch ₃ 2-OH-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-OH-C ₆ H ₄ Propyn-3-yl ch ₃ 2-OH-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-OH-C ₆ H ₄ H ch ₃ 3-OH-C ₆ H ₄ ch ₃ ch ₃ 3-OH-C ₆ H ₄ ^C 2 ^H 5 ch ₃ 3-OH-C ₆ H ₄ nC ₃ H ₇ ch ₃ 3-OH-C ₆ H ₄ 1-C3H7 ch ₃ 3-OH-C ₆ H ₄ nC ₄ Hg ch ₃ 3-OH-C ₆ H ₄ tC ₄ Hg ch ₃ 3-OH-C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 3-OH-C ₆ H ₄ Prop-en-3-yl ch ₃ 3-OH-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-OH-C ₆ H ₄ Propyn-3-yl ch ₃ 3-OH-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-OH-C ₆ H ₄ H ch ₃ 4-OH-C ₆ H ₄ ch ₃ ch ₃ 4-OH-C ₆ H ₄ ^C 2 ^H 5 ch ₃ 4-OH-C ₆ H ₄ nC ₃ H ₇ ch ₃ 4-OH-C ₆ H ₄ I-

R ³ R ⁴ R ⁵ ch ₃ 4-OH-C ₆ H ₄ n ~ C ₄ Hg ch ₃ 4-OH-C ₆ H ₄ t C ₄ H _g ch ₃ 4-OH-C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 4-OH-C ₆ H ₄ Prop-en-3-yl ch ₃ 4-OH-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-OH-C ₆ H ₄ Propyn-3-yl ch ₃ 4-OH-C ₆ H ₄ 3-methyl-but-2-en-l-yl ^CH 3 2-OCH ₃ -C ₆ H ₄ H ch ₃ 2-OCH ₃ -C ₆ H ₄ ch ₃ ch ₃ 2-OCH ₃ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-OCH ₃ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 2-OCH ₃ -C ₆ H ₄ 1-C3H7 ch ₃ 2-OCH ₃ -C ₆ H ₄ ^NC 4H ₉ ch ₃ 2-OCH ₃ -C ₆ H ₄ tC ₄ H ₉ ch ₃ 2-OCH ₃ -C ₆ H ₄ ⁿ ~ ^c g ^H l ₃ ^CH 3 2-OCH ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 2-OCH ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-OCH ₃ -C ₆ H ₄ Propyn-3-yl ch ₃ 2-OCH ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-OCH ₃ -C ₆ H ₄ H ch ₃ 3-OCH ₃ -C ₆ H ₄ ch ₃ ch ₃ 3-OCH ₃ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 3-OCH ₃ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 3-OCH ₃ -C ₆ H ₄ 1-C3H7 ^CH 3 3-OCH ₃ -C ₆ H ₄ nC ₄ Hg ch ₃ 3-OCH ₃ -C ₆ H ₄ t C ₄ H _g ch ₃ 3-OCH ₃ -C ₆ H ₄ n CgHis ch _{3 3-OCH3-C 4} H _g Prop-en-3-yl ch ₃ 3-OCH ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch _{3 3-OCH3-C 4} H _g Propyn-3-yl ch ₃ 3-OCH ₃ -C ₈ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-OCH ₃ -C ₈ H ₄ H ^CH 3 4-OCH ₃ -C ₈ H ₄ ch ₃ ch ₃ 4-OCH ₃ -C ₈ H ₄ ^C 2 ^H 5 ch ₃ 4-OCH ₃ -C ₈ H ₄ nC ₃ H ₇ ch ₃ 4-OCH ₃ -C ₆ H ₄ 1-C3H7

R ³ R ⁴ <J1 ^CH 3 4-OCH ₃ -C ₆ H ₄ n ~ C ₄ Hg ch ₃ 4-OCH ₃ -C ₆ H ₄ tC ₄ H ₉ ch ₃ 4-OCH ₃ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 4-OCH ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 4-OCH ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-OCH ₃ -C ₈ H ₄ Propyn-3-yl ^CH 3 4-OCH ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-OC ₂ H ₅ -C ₆ H ₄ H ch ₃ 2- ° ^C 2 ^H 5 - ^C 6 ^H 4 ch ₃ ch ₃ ² ' ^0C 2 ^H 5 - ^C 6 ^H 4 ^C 2 ^H 5 ch ₃ ² - ° ^C 2 ^H 5 - ^C 6 ^H 4 nC ₃ H ₇ ch ₃ 2-OC ₂ H ₅ -C ₆ H ₄ I-C3H7 ch ₃ 2-OC ₂ H ₅ -C ₆ H ₄ n ^- C ₄ Hg ch ₃ 2-OC ₂ ^h 5- ^C 6 ^H 4 tC ₄ H ₉ ch ₃ 2-OC ₂ ^H 5 ^-C 6 ^H 4 ^n_C 6 ^H 13 ^CH 3 2-OC ₂ ^H 5 -C ₆ H ₄ Prop-en-3-yl ch ₃ 2- ° ^C 2 ^H 5 - ^C 6 ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-OC ₂ H ₅ -C ₆ H ₄ Propyn-3-yl ch ₃ 2-OC ₂ H ₅ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-OC ₂ ^h 5- ^C 6 ^H 4 H ch ₃ 3-OC ₂ H ₅ C ₄ H _g ch ₃ ch ₃ 3-OC ₂ H ₅ -C ₆ ^H 4 ^C 2 ^H 5 ch ₃ 3OC ₂ H ₅ -C ₈ H ₄ nC ₃ H ₇ ch ₃ 3-c ₂ h ₅ -c ₆ h ₄ 1-C3H7 ch ₃ ³ ° ^C 2 ^H 5 ^C 6 ^H 4 nC ₄ H ₉ ch ₃ 3-OC ₂ H ₅ -C ₈ H ₄ tC ₄ H ₉ ch ₃ 3-OC ₂ H ₅ -C ₈ H ₄ ^nC 6 ^H 13 ch ₃ ³ -OC ₂ ^h 5 ^-C 6 ^H 4 Prop-en-3-yl ch ₃ 3-OC ₂ ^H 5 ^-C 6 ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-OC ₂ H ₅ -C ₆ H ₄ Propyn-3-yl ch ₃ ³ - ° ^C 2 ^H 5 - ^C 6 ^H 4 3-methyl-but-2-en-l-yl ch ₃ 4-OC ₂ ^h 5- ^c 6H ₄ H ch ₃ 4-OC ₂ H ₅ -C ₈ H ₄ ch ₃ ch ₃ 4-OC ₂ ^H 5 ^-c 6 ^H 4 ^C 2 ^H 5 ch ₃ 4-OC ₂ ^h 5- ^C 6 ^H 4 nC ₃ H ₇ ch ₃ 4-OC ₂ ^h 5 ^c 6 ^h 4 í ^- c ₃ h ₇

R ³ R ⁴ R ⁵ ch ₃ ⁴ - ° ^C 2 ^H 5 - ^C 6 ^H 4 nC ₄ Hg ch ₃ ⁴ -OC ₂ ^h 5- ^C 6 ^H 4 tC ₄ Hg ch ₃ ⁴ -OC ₂ ^h 5- ^C 6 ^H 4 ^nC 6 ^H 13 ch ₃ 4-OC ₂ ^h 5-C ₆ ^h 4 Prop-en-3-yl ch ₃ ⁴ - ° ^C 2 ^H 5 - ^C 6 ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-OC ₂ H ₅ -C ₆ H ₄ Propyn-3-yl ch ₃ ⁴ ° ^C 2 ^H 5 ^C 6 ^H 4 3-methyl-but-2-en-l-yl ch ₃ 2-O- (C ₃ H ₇ ) -C ₆ H ₄ H ch ₃ 2-O- (C ₃ H ₇ ) -C ₆ H ₄ ch ₃ ch ₃ 2-O- (C ₃ H ₇ ) -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-O- (C ₃ H ₇ ) -C ₆ H ₄ nC ₃ H ₇ ch ₃ 2-O- (t-C ₃ H ₇ ) -C ₆ H ₄ I-C3H7 ch ₃ 2-O- (C ₃ H ₇ ) -C ₆ H ₄ nC ₄ Hg ch ₃ 2-O- (C ₃ H ₇ ) -C ₆ H ₄ tC ₄ H ₉ ch ₃ 2-O- (C ₃ H ₇ ) -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 2-O- (C ₃ H ₇ ) -C ₆ H ₄ Prop-en-3-yl ch ₃ 2-O- (t-C ₃ H ₇ ) -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-O- (C ₃ H ₇ ) -C ₆ H ₄ Propyn-3-yl ch ₃ 2-0- (i-C _{3 H?)} C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-O- (iC ₃ H ₇ ) -C ₆ H ₄ H ch ₃ 3-O- (C ₃ H ₇ ) -C ₆ H ₄ ch ₃ ^CH 3 3-O- (t-C ₃ H ₇ ) -C ₆ H ₄ ^c 2 ^H 5 ch ₃ 3-O- (1C ₃ H ₇ ) -C ₆ H ₄ nC ₃ H ₇ ch ₃ 3-O- (C ₃ H ₇ ) -C ₆ H ₄ I-C3H7 ch ₃ 3-O- (t-C ₃ H ₇ ) -C ₆ H ₄ nC ₄ H ₉ ch ₃ 3-0- (C ₃ H ₇ ) C ₆ H ₄ t 'C ₄ H ₉ ch ₃ 3-0- (i-C ₃ H _{7) 4} -C _g H ^n_C 6 ^H 13 ch ₃ 3-O- (C ₃ H ₇ ) -C ₈ H ₄ Prop-en-3-yl ch ₃ 3-0- (i-C ₃ H _{7) 4} -C _g H (E) -l-chloro-prop-l-en-3-yl ^CH 3 3-O- (1C ₃ H ₇ ) -C ₆ H ₄ Propyn-3-yl ch ₃ 3-O- (C ₃ H ₇ ) -C ₈ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-O- (C ₃ H ₇ ) -C ₆ H ₄ H ch ₃ 4-O- (t-C ₃ H ₇ ) -C ₈ H ₄ ch ₃ ch ₃ 4-O- (C ₃ H ₇ ) -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 4-O- (iC ₃ H ₇ ) -C ₈ H ₄ nC ₃ H ₇ ch ₃ 4-0- (i-C _{3 H?)} C ₆ H ₄ I-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4-O ^- (i-C ₃ H ₇₎ -CgH ^ nC ₄ H ₉ ch ₃ 4-O- (1-C ₃ H ₇ ) -C ₈ H ₄ tC ₄ H ₉ ch ₃ 4-O- (C ₃ H ₇ ) - C ₈ H ₄ ^n_C 6 ^H 13 ch ₃ 4 ^_ O (i-C _{3 H?) 4} -CgH Prop-en-3-yl ch ₃ 4- (1- C ₃ H ₇ ) -C ₈ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-O- (C ₃ H ₇ ) -C ₈ H ₄ Propyn-3-yl ch ₃ 4- (iC ₃ H ₇ ) —C ₈ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-O- (tC ₄ H ₉ ) -C ₈ H ₄ H ch ₃ 2-O- (t C ₄ H _g ) -C ₈ H ₄ ch ₃ ch ₃ 2-O- (tC ₄ H ₉ ) -C ₈ H ₄ ^C 2 ^H 5 ch ₃ 2-O- (tC ₄ H ₉ ) -C ₈ H ₄ ^nC 3 ^H 7 ch ₃ 2-O- (tC ₄ H ₉ ) -C ₈ H ₄ iC ₃ ^H 7 ch ₃ 2-O- (t C ₄ H ₉ ) -C ₆ H ₄ n — C ₄ Hg ch ₃ 2-O- (tC ₄ H ₉ ) -C ₈ H ₄ tC ₄ H ₉ ch ₃ 2-O- (tC ₄ H ₉ ) -C ₈ H ₄ ^nC 6 ^H 13 ^CH 3 2-O- (t C ₄ H ₉ ) -C ₆ H ₄ Prop-en-3-yl ch ₃ 2-O- (t C ₄ H ₉ ) -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-O- (tC ₄ H ₉ ) -C ₈ H ₄ Propyn-3-yl ch ₃ 2-O- (tC ₄ H ₉ ) -C ₈ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-O- (t C ₄ H _g ) -C ₆ H ₄ H ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ ch ₃ ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ ^C 2 ^H 5 ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ nc ₃ H ₇ ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ i — c ₃ h ₇ ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ n — c ₄ h ₉ ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ tC ₄ H ₉ ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ ^nC 6 ^H 13 ch ₃ 3-O- (tC ₄ H ₉ ) C ₈ H ₄ Prop-en-3-yl ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ Propyn-3-yl ch ₃ 3-O- (tC ₄ H ₉ ) -C ₈ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-O- (tC ₄ H ₉ ) -C ₈ H ₄ H ch ₃ 4-O- (t C ₄ H ₉ ) -C ₆ H ₄ ch ₃ ch ₃ 4-O- (tC ₄ H ₉ ) -C ₈ H ₄ ^C 2 ^H 5 ch ₃ 4-O- (t C ₄ H _g ) -C ₈ H ₄ i 'C β H y ch ₃ 4-O- (t C ₄ H _g ) -C ₈ H ₄ t-c ₃ h ₇

R ³ R ⁴ R ⁵ ch ₃ 4-O- (t C ₄ H _g ) -C ₆ H ₄ n ~ C ₄ Hg ch ₃ 4-O- (t C ₄ H _g ) -C ₆ H ₄ t-C ₄ Hg ch ₃ 4-O- (tC ₄ Hg) -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 4-O- (tC ₄ Hg) -C ₆ H ₄ Prop-en-3-yl ch ₃ 4-O- (tC ₄ Hg) -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-O- (tC ₄ Hg) -C ₆ H ₄ Propyn-3-yl ch ₃ 4-O- (tC ₄ Hg) -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-CF ₃ -C ₆ H ₄ H ch ₃ 2-CF ₃ -C ₆ H ₄ ch ₃ ^CH 3 2-CF ₃ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-CF ₃ -C ₆ H ₄ ^n_C 3 ^H 7 ch ₃ 2-CF ₃ ^-C 6 H ₄ I-C3H7 ch ₃ 2-CF ₃ -C ₆ H ₄ nC ₄ Hg ch ₃ 2-CF ₃ -C ₆ H ₄ tC ₄ Hg ch ₃ 2-CF ₃ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 2-CF ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 2-CF ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-CF ₃ -C ₆ H ₄ Propyn-3-yl ^CH 3 2-CF ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-CF ₃ -C ₆ H ₄ H ch ₃ 3-CF ₃ -C ₆ H ₄ ch ₃ ch ₃ ³ - ^{CF 3} - ^C 6 ^H 4 ^C 2 ^H 5 ch ₃ 3-CF ₃ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 3-CF ₃ -C ₆ H ₄ s' ^ 3 ^ 7 ch ₃ 3-CF ₃ -C ₆ H ₄ n — C ₄ Hg ch ₃ 3-CF ₃ -C ₆ H ₄ tC ₄ Hg ch ₃ 3-CF ₃ -C ₆ H ₄ ^n_C 6 ^H 13 ch ₃ 3-CF ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 3-CF ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-CF ₃ -C ₆ H ₄ Propyn-3-yl ch ₃ 3-CF ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-CF ₃ -C ₆ ^H 4 H ch ₃ 4-CF ₃ -C ₆ H ₄ ch ₃ ch ₃ 4-CF ₃ - ^c 6 H ₄ ^C 2 ^H 5 ch ₃ 4-CF ₃ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 4-CF ₃ -C ₆ H ₄ t-c ₃ h ₇

R ³ R ⁴ R ⁵ ch ₃ 4-CF ₃ -C ₆ H ₄ nC ₄ Hg ch ₃ 4-cf ₃ -c ₆ h ₄ tC ₄ H ₉ ch ₃ 4-CF ₃ -C ₆ H ₄ ^nC 6 ^H 13 ch _{3 4} -CF ₃ - ^c 6 ^H 4 Prop-en-3-yl ch ₃ 4-CF ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-CF ₃ -C ₆ H ₄ Propyn-3-yl ch ₃ 4-CF ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-NH ₂ -C ₆ H ₄ H ch ₃ 2-NH ₂ -C ₆ H ₄ ch ₃ ch ₃ 2-NH ₂ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-NH ₂ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 2-NH ₂ -C ₆ H ₄ I-C3H7 ch ₃ 2-NH ₂ -C ₆ H ₄ nC ₄ H _g ch ₃ 2-NH ₂ -C ₆ H ₄ T-C ^ Hg ch ₃ 2-NH ₂ -C ₆ H ₄ ^n_C 6 ^H 13 ch ₃ 2-NH ₂ -C ₆ H ₄ Prop-en-3-yl ch ₃ 2-NH ₂ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-NH ₂ -C ₆ H ₄ Propyn-3-yl ch ₃ 2-NH ₂ - ^c 6 ^H 4 3-methyl-but-2-en-l-yl ch ₃ 3-NH ₂ -C ₆ H ₄ H ch ₃ 3-NH ₂ -C ₆ H ₄ ch ₃ ch ₃ 3-NH ₂ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 3-NH ₂ -C ₆ H ₄ ch ₃ 3-NH ₂ -C ₆ H ₄ 1-C3H7 ch ₃ 3-NH ₂ -C ₆ H ₄ nC ₄ H ₉ ch ₃ 3-NH ₂ -C ₆ H ₄ tC ₄ Hg ch ₃ 3-NH ₂ -C ₆ H ₄ ⁿ ' ^C 6 ^H 13 ch ₃ 3-NH ₂ -C ₆ H ₄ Prop-en-3-yl ch ₃ 3-NH ₂ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-NH ₂ -C ₆ H ₄ Propyn-3-yl ch ₃ 3-NH ₂ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-NH ₂ -C ₆ H ₄ H ch ₃ 4-NH ₂ -C ₆ H ₄ ch ₃ ch ₃ ⁴ NH ₂ -C ₆ H ₄ ^c 2 ^h 5 ch ₃ 4-NH ₂ -C ₆ H ₄ R "* 7 CQH ch ₃ 4-NH ₂ -C ₆ H ₄ CI-C ₃ H ₇

no. R ³ R ⁴ R ⁵ 1869 ch ₃ 4-NH ₂ -C ₆ H ₄ nC ₄ H ₉ 1870 ch ₃ 4-NH ₂ -C ₆ H ₄ tC ₄ H ₉ 1871 ch ₃ 4-NH ₂ -C ₆ H ₄ ^{n / a} 6 ^H 13 1872 ch _{3 4} NH ₂ -C ₆ H ₄ Prop-en-3-yl 1873 ch ₃ ⁴ NH ₂ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl 1874 ch ₃ 4-NH ₂ -C ₆ H ₄ Propyn-3-yl 1875 ch ₃ ⁴ -NH ₂ - ^c 6 ^H 4 3-methyl-but-2-en-l-yl 1876 ch ₃ 2-NMe ₂ -C ₆ H ₄ H 1877 ch ₃ 2-NMe ₂ -C ₆ H ₄ ch ₃ 1878 ch ₃ 2-NMe ₂ -C ₆ H ₄ ^C 2 ^H 5 1879 ch ₃ 2-NMe ₂ -C ₆ H ₄ nC ₃ H ₇ 1880 ch ₃ 2-NMe ₂ -C ₆ H ₄ i- ^C 3 ^H 7 1881 ch ₃ 2-NMe ₂ -C ₆ H ₄ nC ₄ H ₉ 1882 ch ₃ 2-NMe ₂ -C ₆ H ₄ tC ₄ H ₉ 1883 ch ₃ 2-NMe ₂ -C ₆ H ₄ ^n_C 6 ^H 13 1884 ch ₃ 2-NMe ₂ -C ₆ H ₄ Prop-en-3-yl 1885 ch ₃ 2-NMe ₂ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl 1886 ch ₃ 2-NMe ₂ -C ₆ H ₄ Propyn-3-yl 1887 ch _{3 2-NMe2 4-C g} H 3-methyl-but-2-en-l-yl 1888 ch ₃ 3-NMe ₂ -C ₆ H ₄ H 1889 ch ₃ 3-NMe ₂ -C ₆ H ₄ ch ₃ 1890 ch ₃ 3-NMe ₂ -C ₆ H ₄ ^C 2 ^H 5 1891 ch ₃ 3-NMe ₂ -C ₆ H ₄ nC ₃ H ₇ 1892 ch ₃ 3-NMe ₂ -C ₆ H ₄ I-C3H7 1893 ch ₃ 3-NMe ₂ -C ₈ H ₄ nC ₄ ^H 9 1894 ch ₃ 3-NMe ₂ -C ₆ H ₄ tC ₄ H ₉ 1895 ^CH 3 3-NMe ₂ -C ₈ H ₄ ^n_C 6 ^H 13 1896 ch ₃ 3-NMe ₂ -C ₈ H ₄ Prop-en-3-yl 1897 ch ₃ 3-NMe ₂ -C ₈ H ₄ (E) -l-chloro-prop-l-en-3-yl 1898 ch ₃ 3-NMe ₂ -C ₈ H ₄ Propyn-3-yl 1899 ch ₃ 3-NMe ₂ -C ₆ H ₄ 3-methyl-but-2-en-l-yl 1900 ch ₃ 4-NMe ₂ -C ₈ H ₄ H 1901 ch ₃ 4-NMe ₂ -C ₆ H ₄ ch ₃ 1902 ch ₃ 4-NMe ₂ -C ₈ H ₄ ^C 2 ^H 5 1903 ch ₃ ⁴ -NMe ₂ -C ₆ H ₄ nC ₃ H ₇ 1904 ch ₃ 4-NMe ₂ -C ₆ H ₄

R ³ R ⁴ R ⁵ ch ₃ 4-NMe ₂ -C ₆ H ₄ nC ₄ H ₉ ch ₃ 4-NMe ₂ -C ₆ H ₄ tc ₄ H ₉ ch ₃ 4-NMe ₂ -C ₆ H ₄ ^n_C 6 ^H 13 ch ₃ 4-NMe ₂ -C ₆ H ₄ Prop-en-3-yl ch ₃ 4-NMe ₂ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-NMe ₂ -C ₆ H ₄ Propyn-3-yl ch ₃ 4-NMe ₂ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-Aminothiocarbonyl-CGH ₄ H ch ₃ 2-Aminothiocarbonyl-CGH ₄ ch ₃ ch ₃ 2-Aminothiocarbonyl-CGH ₄ ^C 2 ^H 5 ch ₃ 2-Aminothiocarbonyl-CGH ₄ nC ₃ H ₇ ch ₃ 2-Aminothiocarbonyl-CGH ₄ 1-C3H7 ch ₃ 2-Aminothiocarbonyl-CGH ₄ n — C ₄ Hg ch ₃ 2-Aminothiocarbonyl-CGH ₄ t 'C ₄ Hg ch ₃ 2-Aminothiocarbonyl-CGH ₄ ^nC 6 ^H 13 ch ₃ 2-Aminothiocarbonyl-C ₆ H ₄ Prop-en-3-yl ch ₃ 2-Aminothiocarbonyl-CGH ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-Aminothiocarbonyl-C ₆ H ₄ Propyn-3-yl ch ₃ 2-Aminothiocarbonyl-C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-Aminothiocarbonyl-CGH ₄ H ch ₃ 3-Aminothiocarbonyl-C ₆ H ₄ CH ₃ ch ₃ 3-Aminothiocarbonyl-CGH ₄ ^c 2 ^H p ch ₃ 3-Aminothiocarbonyl-CGH ₄ ch ₃ 3-Aminothiocarbonyl-CGH ₄ 1-C3H7 ch ₃ 3-Aminothiocarbonyl-CGH ₄ nC ₄ Hg ch ₃ 3-Aminothiocarbonyl-C ₆ H ₄ tC ₄ H ₉ ch ₃ 3-Aminothiocarbonyl-CGH ₄ ^nC 6 ^H 13 ch ₃ 3-Aminothiocarbonyl-CGH ₄ Prop-en-3-yl ch ₃ 3-Aminothiocarbonyl-CGH ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-Aminothiocarbonyl-CGH ₄ Propyn-3-yl ch ₃ 3-Aminothiocarbonyl-CGH ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-Aminothiocarbonyl-CGH ₄ H ch ₃ 4-Aminothiocarbonyl-CGH ₄ ch ₃ ch ₃ 4-Aminothiocarbonyl-CGH ₄ ^c 2 ^H 5 ch ₃ 4-Aminothiocarbonyl-CGH ₄ Η ^- ΟβΗ ₇ ch ₃ 4-Aminothiocarbonyl-CGH ₄ I-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4-Aminothiocarbonyl-CGH ₄ nC ₄ Hg ch ₃ 4-Aminothiocarbonyl-CGH ₄ tC ₄ H ₉ ch ₃ 4-Aminothiocarbonyl-CGH ₄ ^nC 6 ^H 13 ch ₃ 4-Aminothiocarbonyl-CGH ₄ Prop-en-3-yl ch ₃ 4-Aminothiocarbonyl-CGH ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-Aminothiocarbonyl-CGH ₄ Propyn-3-yl ch ₃ 4-Aminothiocarbonyl-CGH ₄ 3-methyl-but-2-en-l-yl ch ₃ 2-OCF ₃ -C ₈ H ₄ H ch ₃ 2-OCF ₃ -C ₈ H ₄ ch ₃ ch ₃ 2-OCF ₃ -C ₈ H ₄ ^C 2 ^ 5 ch ₃ 2-CF ₃ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 2-OCF ₃ -C ₈ H ₄ ^{3- -C} 3 ^H 7 ch ₃ 2-CF ₃ -C ₆ H ₄ n — C ₄ H ₉ ch ₃ 2-OCF ₃ -C ₈ H ₄ t C ₄ H _g ch ₃ 2-OCF ₃ -C ₈ H ₄ nC ₆ ^H ₃ ch ₃ 2-OCF ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 2-OCF ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-CF ₃ -C ₈ H ₄ Propyn-3-yl ch ₃ 2-OCF ₃ -C ₈ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-OCF _3- ^c g ^H 4 H ch ₃ ³ ° CF ₃ ^C 6 ^H 4 ch ₃ ^CH 3 ³ -OCF ₃ -C 8 ^H 4 ^C 2 ^H 5 ch ₃ ³ -OCF ₃ -C ₈ H ₄ nC ₃ H ₇ ch ₃ 3-OCF ₃ -C ₈ H ₄ iC ₃ ^H 7 ^CH 3 ³ -OCF ₃ - ^c g ^H 4 ^nc 4 ^H 9 ch ₃ 3-OCF ₃ -C ₈ H ₄ tC ₄ H ₉ ch ₃ ³ -OCF ₃ - ^c g ^H 4 ^n_C 6 ^H 13 ch ₃ 3-OCF ₃ -C ₈ H ₄ Prop-en-3-yl ch ₃ ³ -OCF ₃ -C ₈ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-OCF ₃ -C ₈ H ₄ Propyn-3-yl ch ₃ 3-OCF ₃ -C ₈ H ₄ 3-methyl-but-2-en-l-yl ch ₃ ⁴ -OCF ₃ -C 8 ^H 4 H ch ₃ 4-OCF ₃ -C ₈ H ₄ ch ₃ ch ₃ 4-OCF ₃ -C ₈ H ₄ ^C 2 ^H 5 ch ₃ ⁴ -OCF ₃ - ^C 6 ^H 4 Π "ΟβΗγ ch ₃ 4-OCF ₃ -C ₈ H ₄ 1-C ₃ H ₇

R ³ R ⁴ R ⁵ ch ₃ 4-OCF ₃ -C ₆ H ₄ n ⁼ C ₄ Hg ch ₃ ⁴ -OCF ₃ - ^C 6 ^H 4 tC ₄ H ₉ ch _{3 4} -ocf ₃ -c ₆ h ₄ ^n_C 6 ^H 13 ch ₃ 4-OCF ₃ -C ₆ H ₄ Prop-en-3-yl ^CH 3 ⁴ - ° ^CF 3 ^C 6 ^H 4 (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-ocf ₃ -c ₆ h ₄ Propyn-3-yl ch ₃ ⁴ -OCF ₃ - ^C 6 ^H 4 3-methyl-but-2-en-l-yl ch ₃ 2-SCH ₃ -C ₆ H ₄ H ch ₃ 2-SCH ₃ -C ₆ H ₄ ch ₃ ch ₃ 2-SCH ₃ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 2-SCH ₃ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 2-SCH ₃ -C ₆ H ₄ I-C3H7 ^CH 3 2-SCH ₃ -C ₆ H ₄ n — C ₄ Hg ch ₃ 2-SCH _{3 4} -C _g H tC ₄ H ₉ ch ₃ 2-SCH ₃ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 2-SCH ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 2-SCH ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 2-SCH ₃ -C ₆ H ₄ Propyn-3-yl ch ₃ 2-SCH ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 3-SCH _{3 4} -C _g H H ch ₃ 3-SCH ₃ -C ₆ H ₄ ch ₃ ch ₃ 3-SCH ₃ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 3-SCH ₃ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 3-SCH ₃ -C ₆ H ₄ i ^- C3H7 ch ₃ 3-SCH ₃ -C ₆ H ₄ ^n_ c ₄ h ₉ ch ₃ 3-SCH ₃ -C ₆ H ₄ t ~ C ₄ H ₉ ch ₃ 3-SCH ₃ -C ₆ H ₄ ^n_C 6 ^H 13 ch ₃ 3-SCH ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 3-SCH ₃ -C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 3-SCH ₃ -C ₆ H ₄ Propyn-3-yl ch ₃ 3-SCH ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch ₃ 4-SCH ₃ -C ₈ H ₄ H ch ₃ 4-SCH ₃ -C ₆ H ₄ ch ₃ ch ₃ 4-SCH ₃ -C ₆ H ₄ ^C 2 ^H 5 ch ₃ 4-SCH ₃ -C ₆ H ₄ nC ₃ H ₇ ch ₃ 4-SCH ₃ -C ₆ H ₄ 1-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4-SCH ₃ -C ₈ H ₄ nC ₄ H _g ch ₃ 4-SCH ₃ -C ₆ H ₄ tC ₄ H ₉ ch ₃ 4-SCH ₃ -C ₆ H ₄ ^nC 6 ^H 13 ch ₃ 4-SCH ₃ -C ₆ H ₄ Prop-en-3-yl ch ₃ 4-SCH ₃ -C ₈ H ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-SCH ₃ -C ₆ H ₄ Propyn-3-yl ch ₃ 4-SCH ₃ -C ₆ H ₄ 3-methyl-but-2-en-l-yl ch _{3 2-methylsulphonyl-4} CGH H ch _{3 2-methylsulphonyl-4} CGH ch ₃ ch _{3 2-methylsulphonyl-4} CGH ^C 2 ^H 5 ch _{3 2-methylsulphonyl-4} CGH nC ₃ H ₇ ch _{3 2-methylsulphonyl-4} CGH i ^- ^ 3 ^ 7 ch _{3 2-methylsulphonyl-4} CGH nC ₄ H ₉ ch _{3 2-methylsulphonyl-4} CGH t ~ C ₄ H ₉ ch _{3 2-methylsulphonyl-4} CGH ^nC 6 ^H 13 ch _{3 2-methylsulphonyl-4} CGH Prop-en-3-yl ch _{3 2-methylsulphonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ch _{3 2-methylsulphonyl-4} CGH Propyn-3-yl ch _{3 2-methylsulphonyl-4} CGH 3-methyl-but-2-en-l-yl ch _{3 3-methylsulphonyl-4} CGH H ch _{3 3-methylsulphonyl-4} CGH ch ₃ ch _{3 3-methylsulphonyl-4} CGH ^C 2 ^H 5 ch _{3 3-methylsulphonyl-4} CGH nC ₃ H ₇ ch _{3 3-methylsulphonyl-4} CGH CI-C ₃ H ₇ ch _{3 3-methylsulphonyl-4} CGH ⁿ -C ₄ H ₉ ch _{3 3-methylsulphonyl-4} CGH tC ₄ H ₉ ch _{3 3-methylsulphonyl-4} CGH ⁿ ~ ^c g ^H 13 ^CH 3 _{3-methylsulphonyl-4} CGH Prop-en-3-yl ch _{3 3-methylsulphonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ch _{3 3-methylsulphonyl-4} CGH Propyn-3-yl ^CH 3 _{3-methylsulphonyl-4} CGH 3-methyl-but-2-en-l-yl ch _{3 4-methylsulphonyl-4} CGH H ch _{3 4-methylsulphonyl-4} CGH ch ₃ ch _{3 4-methylsulphonyl-4} CGH ^C 2 ^H 5 ch _{3 4-methylsulphonyl-4} CGH nC ₃ H ₇ ch _{3 4-methylsulphonyl-4} CGH t-c ₃ h ₇

R ³ R ⁴ R ^{5 CH} 3 4-Methylsulfonyl-C ₆ H ₄ n — C ₄ Hg ch ₃ 4-Methylsulfonyl-C ₆ H ₄ tC ₄ H ₉ ch ₃ 4-Methylsulfonyl-C ₆ H ₄ ^nC 6 ^H 13 ch _{3 4-methylsulphonyl-4} CGH Prop-en-3-yl ch _{3 4-methylsulphonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-Methylsulfonyl-C ₆ H ₄ Propyn-3-yl ch _{3 4-methylsulphonyl-4} CGH 3-methyl-but-2-en-l-yl ch _{3 2-methoxycarbonyl-4} CGH H ch _{3 2-methoxycarbonyl-4} CGH ch ₃ ch ₃ 2-Methoxycarbonyl-C ₆ H ₄ ^C 2 ^H 5 ch _{3 2-methoxycarbonyl-4} CGH n-C ch _{3 2-methoxycarbonyl-4} CGH t-c ₃ h ₇ ch ₃ 2-Methoxycarbonyl-C ₆ H ₄ nC ₄ H ₉ ch _{3 2-methoxycarbonyl-4} CGH tC ₄ H ₉ ch _{3 2-methoxycarbonyl-4} CGH ⁿ -C ₈ H ₃ ch _{3 2-methoxycarbonyl-4} CGH Prop-en-3-yl ch _{3 2-methoxycarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ch _{3 2-methoxycarbonyl-4} CGH Propyn-3-yl ^CH 3 _{2-methoxycarbonyl-4} CGH 3-methyl-but-2-en-l-yl ch _{3 3-methoxycarbonyl-4} CGH H ^CH 3 _{3-methoxycarbonyl-4} CGH ch ₃ ch ₃ 3-Metoxykarbony1 -C ₄ gH ^c 2 ^H 5 ch _{3 3-methoxycarbonyl-4} CGH nC ₃ H ₇ ch _{3 3-methoxycarbonyl-4} CGH 1-C3H7 ch _{3 3-methoxycarbonyl-4} CGH nC ₄ Hg ch _{3 3-methoxycarbonyl-4} CGH tC ₄ H ₉ ch _{3 3-methoxycarbonyl-4} CGH ^nC 6 ^H 13 ch _{3 3-methoxycarbonyl-4} CGH Prop-en-3-yl ch _{3 3-methoxycarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ch _{3 3-methoxycarbonyl-4} CGH Propyn-3-yl ch _{3 3-methoxycarbonyl-4} CGH 3-methyl-but-2-en-l-yl ch _{3 4-methoxycarbonyl-4} CGH H ch _{3 4-methoxycarbonyl-4} CGH ch ₃ ch _{3 4-methoxycarbonyl-4} CGH ^C 2 ^H 5 ch _{3 4-methoxycarbonyl-4} CGH nC ₃ H ₇ ch _{3 4-methoxycarbonyl-4} CGH 1-C3H7

no. R ³ R ⁴ R ⁵ 2085 ch _{3 4-methoxycarbonyl-4} CGH nC ₄ Hg 2086 ch ₃ 4-Metoxykarbony1 -C ₄ gH tC ₄ H ₉ 2087 ch _{3 4-methoxycarbonyl-4} CGH ⁿ ' ^C 6 ^H 13 2088 ch _{3 4-methoxycarbonyl-4} CGH Prop-en-3-yl 2089 ch _{3 4-methoxycarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl 2090 ch _{3 4-methoxycarbonyl-4} CGH Propyn-3-yl 2091 ch _{3 4-methoxycarbonyl-4} CGH 3-methyl-but-2-en-l-yl 2092 ch _{3 2-ethoxycarbonyl-4} CGH H 2093 ch _{3 2-ethoxycarbonyl-4} CGH ch ₃ 2094 ch _{3 2-ethoxycarbonyl-4} CGH ^C 2 ^H 5 2095 ch _{3 2-ethoxycarbonyl-4} CGH nC ₃ H ₇ 2096 ch _{3 2-ethoxycarbonyl-4} CGH t-c ₃ h ₇ - 2097 ch _{3 2-ethoxycarbonyl-4} CGH n — C ₄ H ₉ 2098 ch _{3 2-ethoxycarbonyl-4} CGH tC ₄ H ₉ 2099 ch _{3 2-ethoxycarbonyl-4} CGH ^nC 6 ^H 13 2100 ch _{3 2-ethoxycarbonyl-4} CGH Prop-en-3-yl 2101 ch _{3 2-ethoxycarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl 2102 ch _{3 2-ethoxycarbonyl-4} CGH Propyn-3-yl 2103 ^CH 3 _{2-ethoxycarbonyl-4} CGH 3-methyl-but-2-en-l-yl 2104 ch _{3 3-ethoxycarbonyl-4} CGH H 2105 ch _{3 3-ethoxycarbonyl-4} CGH ch ₃ 2106 ch _{3 3-ethoxycarbonyl-4} CGH ^c 2 ^H 5 2107 ch _{3 3-ethoxycarbonyl-4} CGH nC ₃ H ₇ 2108 ch _{3 3-ethoxycarbonyl-4} CGH i-C-JH? 2109 ch _{3 3-ethoxycarbonyl-4} CGH nC ₄ H _g 2110 ch _{3 3-ethoxycarbonyl-4} CGH tC ₄ H ₉ 2111 ch _{3 3-ethoxycarbonyl-4} CGH ^nC 6 ^H 13 2112 ch _{3 3-ethoxycarbonyl-4} CGH Prop-en-3-yl 2113 ch _{3 3-ethoxycarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl 2114 ch _{3 3-ethoxycarbonyl-4} CGH Propyn-3-yl 2115 ch _{3 3-ethoxycarbonyl-4} CGH 3-methyl-but-2-en-1-yl 2116 ch _{3 4-ethoxycarbonyl-4} CGH H 2117 ch _{3 4-ethoxycarbonyl-4} CGH ^CH 3 2118 ch _{3 4-ethoxycarbonyl-4} CGH ^C 2 ^H 5 2119 ch _{3 4-ethoxycarbonyl-4} CGH nC ₃ H ₇ 2120 ch _{3 4-ethoxycarbonyl-4} CGH I-C3H7

R ³ R ⁴ R ⁵ ch _{3 4-ethoxycarbonyl-4} CGH nC ₄ Hg ^CH 3 _{4-ethoxycarbonyl-4} CGH tC ₄ H ₉ ch _{3 4-ethoxycarbonyl-4} CGH nC ₆ ^H 13 ch _{3 4-ethoxycarbonyl-4} CGH Prop-en-3-yl ch _{3 4-ethoxycarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ch ₃ 4-Ethoxycarbonyl-C ₆ H ₄ Propyn-3-yl ch _{3 4-ethoxycarbonyl-4} CGH 3-methyl-but-2-en-l-yl ch _{3 2-Aminocarbonyl-4} CGH H ch ₃ 2-Aitiinokarbonyl _CGH-4 ch ₃ ^CH 3 _{2-Aminocarbonyl-4} CGH ^C 2 ^H 5 ch _{3 2-Aminocarbonyl-4} CGH Γ1 "0βΗγ ch _{3 2-Aminocarbonyl-4} CGH i- ^C 3 ^H 7 ch _{3 2-Aminocarbonyl-4} CGH nC ₄ H ₉ ch _{3 2-Aminocarbonyl-4} CGH tC ₄ H ₉ ch ₃ 2-Aminocarbonyl-C ₆ H ₄ ^nC 6 ^H 13 gh _{3 2-Aminocarbonyl-4} CGH Prop-en-3-yl ch _{3 2-Aminocarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ch _{3 2-Aminocarbonyl-4} CGH Propyn-3-yl ch _{3 2-Aminocarbonyl-4} CGH 3-methyl-but-2-en-l-yl ch ₃ 3-aminocarbonyl-C ₆ H ₄ H ch _{3 3-Aminocarbonyl-4} CGH ch ₃ ch _{3 3-Aminocarbonyl-4} CGH ^C 2 ^H 5 ch _{3 3-Aminocarbonyl-4} CGH nC ₃ H ₇ ch _{3 3-Aminocarbonyl-4} CGH 1-C3H7 ch _{3 3-Aminocarbonyl-4} CGH nC ₄ H _g ch _{3 3-Aminocarbonyl-4} CGH t C ₄ H _g ch _{3 3-Aminocarbonyl-4} CGH ^nC 6 ^H 13 ch _{3 3-Aminocarbonyl-4} CGH Prop-en-3-yl ch _{3 3-Aminocarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ^CH 3 _{3-Aminocarbonyl-4} CGH Propyn-3-yl ch _{3 3-Aminocarbonyl-4} CGH 3-methyl-but-2-en-l-yl ch _{3 4-Aminocarbonyl-4} CGH H ^CH 3 _{4-Aminocarbonyl-4} CGH ch ₃ ch _{3 4-Aminocarbonyl-4} CGH ^C 2 ^H 5 ch _{3 4-Aminocarbonyl-4} CGH nC ₃ H ₇ ch _{3 4-Aminocarbonyl-4} CGH 1-C3H7

R ³ R ⁴ R ⁵ ch ₃ f 4-Aminocarbonyl-C 8 H ₄ n — c ₄ Hg ch _{3 4-Aminocarbonyl-4} CGH tC ₄ H ₉ ch _{3 4-Aminocarbonyl-4} CGH ^nC 6 ^H 13 ch _{3 4-Aminocarbonyl-4} CGH Prop-en-3-yl ch _{3 4-Aminocarbonyl-4} CGH (E) -1-chloro-prop-l- en-3-yl ch _{3 4-Aminocarbonyl-4} CGH Propyn-3-yl ch _{3 4-Aminocarbonyl-4} CGH 3-methyl-but-2-ene 1-yl ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ H ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ ch ₃ ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ 5 ', 2' ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ nC ₃ H ₇ ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ iC ₃ H ₇ ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ nC ₄ H ₉ ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ tC ₄ H ₉ ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ ^nC 6 ^H 13 ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ Prop-en-3-yl ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ (E) -1-chloro-prop-l en-3-yl ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ Propyn-3-yl ch ₃ 2- (N-methylaminocarbonyl) -CgH ₄ 3-methyl-but-2-ene 1-yl ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ H ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ ch ₃ ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ ^C 2 ^H 5 ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ nC ₃ H ₇ ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ I-C3H7 ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ nC ₄ H ₉ ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ tC ₄ H ₉ ^CH 3 3- (N-methylaminocarbonyl) -CgH ₄ ^nC 6 ^H 13 ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ Prop-en-3-yl ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ (E) -1-chloro-prop-l en-3-yl ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ Propyn-3-yl ch ₃ 3- (N-methylaminocarbonyl) -CgH ₄ 3-methyl-but-2-ene 1-yl ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ H ^CH 3 4- (N-methylaminocarbonyl) -CgH ₄ ^CH 3 ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ ^C 2 ^H 5 ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ n ™ C β H * y ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ 1-C3H7

R ³ R ⁴ R ⁵ ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ n ~ C ₄ Hg ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ tC ₄ H ₉ ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ ⁿ ' ^C 6 ^H 13 ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ Prop-en-3-yl ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ (E) -l-chloro-prop-l-en-3-yl ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ Propyn-3-yl ch ₃ 4- (N-methylaminocarbonyl) -CgH ₄ 3-methyl-but-2-en-l-yl ch _{3 2-dimethylaminocarbonyl-4} CGH H ch _{3 2-dimethylaminocarbonyl-4} CGH ch ₃ ch _{3 2-dimethylaminocarbonyl-4} CGH ^C 2 ^H 5 ch _{3 2-dimethylaminocarbonyl-4} CGH N ^ C ^ H'y ch _{3 2-dimethylaminocarbonyl-4} CGH 1-C3H7 ch _{3 2-dimethylaminocarbonyl-4} CGH nC ₄ H ₉ ch _{3 2-dimethylaminocarbonyl-4} CGH tC ₄ H ₉ ch _{3 2-dimethylaminocarbonyl-4} CGH ^nC 6 ^H 13 ch _{3 2-dimethylaminocarbonyl-4} CGH Prop-en-3-yl ch _{3 2-dimethylaminocarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ch _{3 2-dimethylaminocarbonyl-4} CGH Propyn-3-yl ch _{3 2-dimethylaminocarbonyl-4} CGH 3-methyl-but-2-en-l-yl ch _{3 3-dimethylaminocarbonyl-4} CGH H ch _{3 3-dimethylaminocarbonyl-4} CGH ch ₃ ch _{3 3-dimethylaminocarbonyl-4} CGH ^C 2 ^H 5 ch _{3 3-dimethylaminocarbonyl-4} CGH nC ₃ H ₇ ch _{3 3-dimethylaminocarbonyl-4} CGH i-CsHy ch _{3 3-dimethylaminocarbonyl-4} CGH n — C ₄ Hg ch _{3 3-dimethylaminocarbonyl-4} CGH tC ₄ H ₉ ch _{3 3-dimethylaminocarbonyl-4} CGH ^nC 6 ^H 13 ch _{3 3-dimethylaminocarbonyl-4} CGH Prop-en-3-yl ch _{3 3-dimethylaminocarbonyl-4} CGH (E) -l-chloro-prop-l-en-3-yl ch _{3 3-dimethylaminocarbonyl-4} CGH Propyn-3-yl ch _{3 3-dimethylaminocarbonyl-4} CGH 3-methyl-but-2-en-l-yl ch _{3 4-dimethylaminocarbonyl-4} CGH H ch _{3 4-dimethylaminocarbonyl-4} CGH ^CH 3 ch _{3 4-dimethylaminocarbonyl-4} CGH ^c 2 ^h 5 ch _{3 4-dimethylaminocarbonyl-4} CGH nc ₃ H ₇ ch _{3 4-dimethylaminocarbonyl-4} CGH I ^- C ₃ H ₇

no. R ³ R ⁴ R ⁵ 2229 ch _{3 4-dimethylaminocarbonyl-4} CGH nC ₄ H ₉ 2230 ch _{3 4-dimethylaminocarbonyl-4} CGH tC ₄ H ₉ 2231 ch ₃ 4-Dimethylaminocarbonyl-C ₆ H ₄ ^n_C 6 ^H 13 2232 ch _{3 4-dimethylaminocarbonyl-4} CGH Prop-en-3-yl 2233 ch ₃ 4-Dimethylaminocarbonyl-C ₆ H ₄ (E) -l-chloro-prop-l-en-3-yl 2234 ch _{3 4-dimethylaminocarbonyl-4} CGH Propyn-3-yl 2235 ch _{3 4-dimethylaminocarbonyl-4} CGH 3-methyl-but-2-en-l-yl

The compounds of formula I are useful as fungicides.

The compounds of the formula I are distinguished by excellent activity against a wide range of plant pathogenic fungi, in particular from the class Ascomycetes and Basidiomycetes. They are partially systemically active and can be used as foliar and soil fungicides.

They are of particular importance in the destruction of many fungi on various crop plants such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybeans, coffee, sugarcane, vine, fruit and ornamental plants and vegetables such as cucumbers, beans and pumpkin as well as on the seeds of these plants.

They are particularly advantageous in the control of the following plant diseases: Erysiphe graminis (powdery mildew), grain, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podospharea leucotricha on apples, Uncinula necator on grapevine, Puccinia on grasshopper, Grain species, Grain species, Ustilago for grain and sugar cane, Venturia inaequalis (apple tree), Helminthosporium for grain, Septoria nodorum for wheat, Botrytis cinerea for strawberry, grapevine, Cercospora arachidicola for peanut, Pseudocercosporella wheatpotricia, on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viticola on vines, Alternatia species on vegetables and fruits.

The compounds of the formula I are used by treating fungi or fungal-protected plants, seeds, materials or soil with a fungicidally effective amount of the active ingredient. The treatment is carried out before or after fungal infection of the materials, plants or seeds.

The compounds of the formula I can be converted into the customary formulations such as solutions, emulsions, suspensions, powder, pastes and granules. The form of use depends on the individual purpose of use, in any case it should allow for a fine and even distribution of the ortho-substituted cyclopropanecarboxylic acid benzyl ester. The formulations are prepared in a known manner, for example by adding the active ingredient with solvents and / or carriers, if necessary using emulsifying and dispersing agents, and in the case of water as a diluent other organic solvents can also be used as auxiliary agents. Possible excipients are: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzene), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water; carriers such as natural stone meal (e.g. kaolin, clays, talc, chalk) and synthetic stone meal (e.g. highly dispersed silica, silicates), emulsifying agents such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol-ether, alkylsulfonates and arylasulfonates) and dispersing agents such as lignin-sulfite leachates and methylcellulose.

The fungicidal agents generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight. of the active substance.

Depending on the type of effect desired, the amounts used are between 0.01 and 2.0 kg of active substance per ha.

In the treatment of seed, an amount of active compound of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kilogram of seed is generally required.

The formulations according to the invention may also be present in the form of application together with other active substances such as herbicides, insecticides, growth regulators, fungicides or even fertilizers.

When mixed with fungicides, in many cases an increase in the spectrum of fungicidal activity is obtained.

The following lists of fungicides, together with which the compounds of the invention may be used, illustrate the combination possibilities, but do not limit them in any way:

Sulfur, dithiocarbamates and derivatives thereof such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese zinc ethylenediamine bis-dithiocarbamate, detramethiyl thiametyl amine, tetramethiyl thiametyl amine; ammonia-zinc (N, N'-propylene-bis-dithiocarbamate) complex, zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis (thiocarbamoyl) disulfide;

nitro derivatives such as dinitro (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethyl acrylate, 2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate, 5-nitro-isophthalic acid diisopropyl ester;

heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) s-triazine, O, O-diethylphthalimidophosphonothioate, 5-amino-1- [bis- (dimethylamino)) -phosphinyl] -3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-ditit 4,5-b] quinoxaline, 1- (butylcarbamoyl) methyl ester -2-benzimidazole-carbamic acid, 2-methoxycarbonylamino- (4) -benzimidazole, N- (1,1,2,2-tetrachloroethylthio) -tetrahydrophthalimide, N-trichloromethylthio-tetrahydrophthalimide, N-trichloromethylthiophthalimide, N-dichlorofluoromethylthio diamide -N ', N'-dimethyl-N-phenylsulphuric acid, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-rodanomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4- (2- chlorophenylhydrazono) -3-methyl-5-isoxazolone, pyridine-2-thio-1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1-, 4-oxathien 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathien-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid anilide, acid anilide 2 methyl furan-3-carboxylic acid, 2,5-dimethylfuran-3-carboxylic acid anilide, 2,4,5-trimethylfuran-3-carboxylic acid anilide, 2,5-dimethylfuran-3-carboxylic acid cyclohexylamide, N-cylohexyl acid amide -N-methoxy-2,5-dimethyl-furan-3-carboxylic acid, 2-methylbenzoic acid anilide, 2-iodo-benzoic acid anilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1 4-Diyl- (1- (2,2,2-trichloroethyl) -formamide, 1- (3,4-dichloroanilino) -1-formylamino-2,2,2-trichloroethane, 2,6-dimethyl-N- tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclodecylmorpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpropyl] -cis-2,6-dimethylmorpholine, N- [3- ( p-tert-butylphenyl) -2-methylpropyl] -piperidine, 1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4 -triazole, 1- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, N- (n- propyl) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazol-yl-urea, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazole) 1-yl) -2-b utanone, 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol, α- (2-chlorophenyl) -a- (4 chlorophenyl) -5-pyrimidine methanol.

5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis- (p-chlorophenyl) -3-pyridinemethanol, 1,2-bis- (3-ethoxycarbonyl-2-thioureido) -benzene, 1,2- bis- (3-methoxycarbonyl-2-thioureido) -benzene as well as various fungicides such as dodecylguanidinoacetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] -glutarimide, hexachlorobenzene, DL- N- (2'-Methoxyacetyl) -alanine methyl ester, N- (2-Methoxyacetyl) -N-furoyl (2) -alaninate, N- (2'-Methoxyacetyl) -alanine methyl ester , 6-dimethylphenyl) -N-chloroacetyl-DL-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) -alanine methyl ester, 5-methyl-5-vinyl-3- (3,5 -dichlorophenyl) -2,4-dioxo-1,3-oxazolidine, 3- [3,5-dichlorophenyl-5-methyl-5-methoxymethyl] -1,3-oxazolidine-2,4-dione,

3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboxylic acid imide, 2-cyano- [N-ethylaminocarbonyl) -2- methoxyimino] -acetamide, 1- [2- (2,4-dichlorophenyl) -pentyl] -1H-1,2,4-triazole, 2,4-difluoro-α- (1H-1,2,4-triazolyl- 1-methyl) -benzhydryl alcohol, N- (3-chloro-2,6-dinitro-4-trifluoromethylphenyl) -5-trifluoro-3-chloro-2-aminopyridine, 1 - ((bis- (4-fluorophenyl)) (methylsilyl) methyl) -1H-1,2,4-triazole.

In addition, the compounds of the formula I are suitable for the effective control of insect, spider and nematode pests. They can be used effectively in plant protection as well as in the hygiene, storage and veterinary sectors as a pest control agent.

The harmful insects include, for example, Lepidoptera, such as Agrotis ypsilon, Agrotis segetum, Alabama argicellacea, Anticarsia gemmatalis, Argyrestia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Cypress cactus, Cleimatobia brumata, Cleimatobia brumata, Cleimatobia brumata Pomonella, Dendrolimud pini, Diaphania nitidalis, Diatraea grandiosell, Earias insulana, Elaasmopalpus lignosellus, Eupoecilia ambiguella, Fetria suterranea, Galleria mellonella, Grapholitha funebrana, Holiothis, Heliothis, Heliothis, Heliothis, Heliothis, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria monarpellica, Lymantria monarica, ia pseditsugata, Ostrinia nubilalis, Panolis flammea, Pectophora gossypiella, Peridroma saucia, Phalera bucephala, Phtorimae operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia scia, Pseudoplusia scia Spotoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.

From the range of beetles (Coleoptera), for example, Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthomonus pomorum, Atomaria linearis, Blastophagus piniperda, Bithophaga undata, Bruchus rufususisus, Bruchus rufususisus, Nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Dia95 brotica, Abbrusica virgifera, Episutisnis, Epilautitnis Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lisssorthorus oryzophilus, Melanotus communis, Meligontes hippocastani, Melolontha melolontha, Onlema oryzae, Ortiorushynchuschnusneacnusneacnusnn ophaga sp., Phyllopertha horticola, Phylotreta nenorum, Phyllotreta striolata, Popia japonica, Sitona lineatus, Sitophilus granaria.

Among the diptera species, for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomia hominovorax, Chrysomia macellaria, Cordranobia anthropus, Cordylobia anthropus, Cordylobia anthropus, canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haploidiplosis equestris, Hylemyia platura, Hypoderma lineata; Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagolestis cerasi, Rhagolestis pomonella, Tabanus bovinus, Tipula oleracea, Tipula paludosa.

Among the tufts (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella triciti, Scirtothrips citri, Thips oryzae, Thrips palmi, Thrips tabaci.

Among the Hymenoptera, for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis gemitana, Solenopsis invicta.

From the order of the Heteroptera, for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus,

Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.

From the family of homoptera, for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Bradychycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii, Drosea, Drosiaeamanisolae, Drosiaeamanisolae, Daphne, Avenae, Macrosiphum euphorbiae, Macrosiphum rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phoron humuli, Sylapapis, Sapapapis, Rhosalisus, Rhopalomus, Rhopalomus Schizapsis graminum, Schizoneura lanuginosa, Vialus vitifolii, Trialeurodes vaporarium.

From the series of termites (Isoptera), for example, Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termes natalensis.

In the range of Orthoptera, for example, Acheta domestica, Blatta orientalis, Blatella germanica, Forficula auricularia, Gryllotarpa gryllotarpa, Locusta migratoria, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus spp. Schistocerca pergina, Stauronotus maroccanus, Tachycines asynamorus.

From the class of the Aracnoidea, for example, mites (Acarina) such as Amblyoma americanum, Amblyoma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicus, Bryobia praetiosa, Dermacentor silvarum, Iotetranychus ricus, , Ornithodorus moubata, Otobius megnini, Paratetrachynus pilosus, Phalocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes

- 97 oats, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabei, Tetranychus cinnabarinus, Tetranychus kanzawal, Tetranychus pacificus, Tetranychus teparius, Tetranychus urticae.

From the class of nematodes, for example, root nematodes, for example Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, for example Globodera rostichiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Deterodonus longensususus, Dulceususlenes, Multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus curvitatus, Pratylenchus goodeyi.

DETAILED DESCRIPTION OF THE INVENTION

The active compounds can be used in the form of their formulations or their application forms, for example, in the form of dispersions, emulsions, oil dispersions, pastes, dusts, dusting powders, granules, spraying, fogging, spraying, pouring or pouring. The dosage forms depend on the intended use; in any case, they must allow a fine distribution of the active compounds according to the invention.

The concentrations of the active ingredients in ready-to-use preparations can vary widely.

In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%:

The active ingredients can also be used with good results in the ultra-low-volume (ULV) process, wherein the formulations can be prepared with more than 95% by weight. or as an active ingredient without additives.

The amount of pest control agent used in the open soil conditions is 0.1 to 2.0, preferably 0.2 to 1.0 kg / ha.

For the production of directly injectable solutions, emulsions, pastes or oil dispersions, suitable fractions of medium to high boiling mineral oils such as kerosene or diesel oil, coal tar oils as well as vegetable or animal oils, aliphatic, cyclic and aromatic hydrocarbons are suitable, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strong polar solvent such as dimethylformamide, dimethylsulfoxide, N-methylsulfoxide, N-methylsulfoxide , Water.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (spray powder, oil dispersions) by the addition of water. For the production of emulsions, pastes or oil dispersions, the components may be used as such or may be homogenized dissolved in an oil or solvent, using a wettable, tacky, dispersing or emulsifying agent. However, it is also possible to make concentrates which are suitable for dilution with water from the active ingredient, wettable, tacky, dispersing or emulsifying agent and any solvent or oil.

Suitable surfactants are alkali metal, alkaline earth metal salts, ammonium salts of ligninsulfonic acids, naphthalenesulfonic acids, phenolsulfonic acids, dibutylnaphthalenesulfonic acids, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty metal sulfates and their fatty alcohol sulfates alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated izo99 octylphenol, octylphenol or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, condensates of polyoxyethylene alkyl ether, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, lignosulfite leaches and methylcellulose.

Powder, spray and dust compositions can be prepared by mixing or grinding the active ingredients with a solid carrier.

The formulations generally comprise between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight. of the active substance. The active compounds can have a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

Examples of formulations are:

I. 5 wt. parts by weight of the active compound are intensively mixed with 95 wt. finely divided kaolin. A dusting composition is thus obtained which contains 5 wt. of the active substance.

II. 30 wt. parts of the active ingredient are mixed well with a mixture of 92 wt. parts by weight of silica gel powder and 8 wt. parts of paraffin oil which has been sprayed onto the surface of this silica gel. In this way, a preparation is obtained which contains an active substance with good adhesion (active substance content 23% by weight).

III. 10 wt. parts of the active ingredient are dissolved in a mixture of 90 wt. parts by weight of xylene, 6 wt. parts by weight of the addition product of 8 to 10 moles of ethylene oxide per mole of oleic acid N-monoethanolamide, 2 wt. parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 wt. parts of the adduct 40 ml of ethylene oxide per mole of castor oil (active ingredient content 9% by weight).

100

IV. 20 wt. parts are dissolved in a mixture of 60 wt. parts by weight of cyclohexanone, 30 wt. parts by weight of isobutanol, 5 wt. parts by weight of the addition product of 7 moles of ethylene oxide per mole of isooctylphenol and 5 wt. parts of the adduct 40 ml of ethylene oxide per mole of castor oil (active ingredient content 16% by weight).

80 wt. 3 parts by weight of the active ingredient are well mixed with 3 wt.

parts by weight of dii sodium salt 10 wt. parts by weight of sodium sulphite liquor and 7 wt. and grinded in a hammer mill by weight).

zobutylnaphthalene-α-sulfonic acid, ligninsulfonic acid, from parts of powdered silica (active substance content 80%)

VI. 90 wt. parts of active ingredient with 10 wt. parts of N-methyl-.alpha.-pyrrolidone to give a solution suitable for use in the form of the smallest droplets (active ingredient content 90% by weight).

VII. 20 wt. parts of the active ingredient are dissolved in a mixture of 40 wt. parts by weight of cyclohexanone, 30 wt. parts by weight of isobutanol, 20 wt. parts by weight of the addition product of 7 moles of ethylene oxide per mole of isooctylphenol and 10 wt. parts of the addition product of 40 moles of ethylene oxide per mole of castor oil. Pouring and finely distributing the solution into 100,000 wt. parts of water to obtain an aqueous dispersion containing 0.02 wt. % of active substance.

VIII. 20 wt. 3 parts by weight of the active compound are well mixed with 3 wt. % by weight of diisobutylnaphthalene-α-sulfonic acid sodium salt, 19 wt. parts by weight of sodium lignin sulphonic acid from a sulphite liquor and 60 wt. pieces of silica gel powder and ground in a hammer mill. By finely distributing the mixture in 20,000 wt. parts of water to obtain a spray liquor containing 0.1 wt. of the active substance.

Granules, optionally coated, impregnated and homogeneous granules can be prepared by binding the active ingredient to a solid

101 rack. Solid carriers are, for example, mineral clays such as silica gel, silica, silica, silicates, talc, kaolin attaclay, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics , fertilizer such as ammonium sulfate, ammonium nitrate, urea and plant products such as cereal flour, tree bark flour, wood and nut shells, cellulose powder and other solids.

Various types of oils, herbicides, fungicides, other pest control agents, bactericides, possibly also immediately before use (tankmix), can be added to the active ingredients. These agents may be added to the compositions of the invention in a weight ratio of 1: 10 to 10: 1.

Synthesis examples

In the following synthesis examples, the above procedures can be used, with the corresponding variation of the starting compounds, to prepare other compounds of formula I. The compounds thus obtained are listed in the following tables with physical values.

Synthesis examples

Example 1

Preparation of (E, E) -2-Methoxyimino-2- [1-methyl, -1-acetyl) -iminooxymethyl] -phenylacetic acid methyl ester

To 6.4 g (0.21 mol) of sodium hydride (80%) in 150 ml of dried dimethylformamide, 21 g (0.21 mol) of diacetylmonoxime are added under protective gas and with gentle cooling at room temperature and the mixture is stirred for 30 minutes at room temperature. A solution of 60 g (0.21 mol) of 2-methoxyimino-2- (2'-bromomethyl) phenylacetic acid methyl ester in 360 ml of dimethylformamide is then added dropwise and stirred for 16 hours at room temperature. After addition of 10% hydrochloric acid, it is extracted with methyl tert-butyl ether. The combined organic phases are washed

102 water, dried over sodium sulfate and evaporated. The residue was suspended with a small amount of cold methanol. After suctioning, 38 g (59%) of the title compound are obtained in the form of light brown crystals, m.p. 69-71 ° C.

¹ H-NMR (CDC1 _3): & = 1.87 (s, 3H), 2.30 (s, 3H), 3.85 (s, 3H), 4.05 (s, 3H), 5.15 (s, 2H), 7.17-7.48 (m, 4H) ppm.

Example 2

Preparation of (E, E, E) -2-Methoxyimino-2- [2 '- (1-methyl, 1- (1'-ethoxyiminoethyl)) iminooxymethyl] phenylacetic acid methyl ester

7.0 g (20 mmol) of (E, E, E) -2-methoxyimino-2- [2 '- (1-methyl, 1- (1'-ethoxyiminoethyl)) iminooxymethyl] phenylacetic acid methyl ester was heated in 60 mL 1 M aqueous KOH solution at 80 ° C for 4 hours. After cooling, it is extracted with methyl tert-butyl ether, the aqueous phase is acidified with semi-concentrated hydrochloric acid and extracted with methyl tert-butyl ether. After washing the organic phase with water, drying (Na ₂ SO ₄ ) and evaporation, 6.0 g of (E, E, E) -2-methoxyimino-2- [2 '- (1-methyl, 1- (1'')) are obtained. (ethoxyiminoethyl) iminooxymethyl] phenylacetic acid as a colorless solid which is then dissolved in 100 ml of dried DMF. After the addition of 2.9 g (18 mmol) of carbobyldiimidazole, it is stirred for 1 hour, then 2.5 g (36 mmol) of sodium methanethiolate are added and further stirred for 16 hours, the mixture is evaporated and the residue is taken up in methyl tert-butyl ether. and water, the organic phase was extracted with 1 M aqueous NaOH, washed with water, dried over Na ₂ SO ₄ and evaporated to give 4.1 g (57%) of the title compound as a light yellow oil.

¹ H-NMR (CDCl ₃ ): δ - 1.27 (t, 3H), 1.95 (s, 3H), 1.98 (s, 3H), 2.33 (S, 3H), 4.05 (s, 3H), 4.17 (q, 2H), 5.03 (s, 2H), 7.12 (m, 4H) ppm.

103

table

(1.1)

no. R ² m R ³ R ⁴ R ⁵ data

H CH ₃ CH ₃ CH ₃ Oil, IR (film): 2935, 1667, 1145-1057, 1030, 1014, 988, 888, 881,

844, 773

H, CH ₃ CH ₃ C ₂ H ₅ Oil, IR (film): 2936, 1679, 1386

1366, 1091, 1047, 1027, 982, 890, 847.

Examples of efficacy against harmful fungi

The fungicidal activity of the compounds of the formula I is demonstrated by the following experiments:

The active ingredients are processed as a 20% emulsion in a mixture consisting of 70% by weight. % cyclohexanone, 20 wt. % By weight of Nekanil ^R LN (Lutensol ^R AP6, an emulsifying and dispersing crosslinker based on ethoxylated alkylphenol) and 10 wt. Emulphor ^R EL (Emulan ^R EL, an ethoxylated fatty alcohol emulsifier) and dilute with water to the appropriate desired concentration.

Erysiphe graminis var. tritici

The leaves of wheat seedlings (Kanzler variety) are first treated with an aqueous active ingredient preparation (63 ppm). After about 24 hours, the plants are dusted with spores of powdery mildew (Erysiphe graminis var. Tritici). The plants thus treated are

T?

- 104 are then incubated for 7 days at a temperature of 20 to 22 ° C, at a relative humidity of 75-80%. The extent of fungal development is then determined.

Herein, the plants treated with the compounds according to the invention showed no attack, which occurred in plants treated with the known active substance (compound No. 497, Table 2, EP-A 463 488) and 40% in untreated plants.

Examples of efficacy against animal pests

The insecticidal activity of the compounds of the formula I is demonstrated by the following experiments:

The active ingredients were prepared as

(a) 0,1% acetone solution; or

b) as a 10% emulsion in a 70 wt. of cyclohexanone, 20% by weight of Nekanil LN (Lutensol AP6, an emulsifying and dispersing crosslinking agent based on ethoxylated alkylphenol) and 10% by weight of cyclohexanone; Emulphor ^R EL (Emulan ^R EL, an ethoxylated fatty alcohol emulsifier) and diluted to an appropriate concentration with acetone in a) and d) respectively. water in case b).

At the end of the experiment, the lowest concentration is always determined at which the compounds still exhibited 80% to 100% inhibition, respectively, in comparison with the untreated control. mortality (efficacy threshold or minimum concentration).

Claims (11)

PATENT CLAIMS Phenylthioacetic acid derivatives of the general formula I (i) wherein the substituents and the index have the following meanings: R ^{@ 1} - represents hydrogen and C1 -C4 -alkyl. n R is cyano, nitro, trifluoromethyl, halogen, C ₁ -C ₄ alkyl, and C - ^ - C ^^ - alkoxy, m is 0, 1 or 2, wherein the radicals R ² can be identical or different when m is 2, ABOUT R is hydrogen, cyano, nitro, hydroxy, amino, halo, C ^ C-j alkyl, C ₁ -C ₄ -haloalkyl, C-C-alkoxy, _C1-C4 haloalkoxy, _C3-C4 -alkylthio, C 1 -C 4 -alkylamino or di-C ₁ -C ₄ -alkylamino, R ⁴ is hydrogen, cyano, nitro, hydroxy, amino, halogen, C -C alkyl, C ₁ ~ C ₆ alkoxy, C -C alkylthio, C - ^ - Cg-alkylamino, di-C ^ -CG- alkylamino, _C2 ~ Cg alkenyl, _C2 ~ Cg-alkenyloxy, C ₂ -C ₆ -alkenyltio, C ₂ -C ₆ ~ alkenylamino, NC ₂ -C ₆ -alkenyl-C ~ -C ^ -alkylamino, _C2 -C-alkynyl, C ₂ -C-alkynyloxy, C ₂ -C-alkynylthio, C ₂ -C-alkynylamino, NC ₂ -C ₆ -alkynyl-NC ^ -C-akylamino, the hydrocarbon radicals of these groups to be partly or fully halogenated or may carry one to three of the following radicals: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkylaminocarbonyl, 106 di-C 1 -C 8 -alkylaminocarbonyl, C 1 -C 8 -alkylaminothiocarbonyl, di C 1 -C 8 -alkylaminothiocarbonyl, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy , C -C alkoxycarbonyl, C ^ -C alkylthio, C ^ -C-alkylamino, di-C-Cg-alkylamino, C ₂ -C alkenyloxy, C ₃ -C -cycloalkyl, C ₃ -C cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C ₁ -C ₄ -alkoxy, arylthio, aryl-C ₄ ° -alkylti, hetaryl, hetaryloxy, _{hetaryl-C1-C4-alkoxy,} hetarylthio, hetaryl-C ₁ -C ₄ -alkylthio, wherein the cyclic radicals may on their side be halogenated partially or fully and / or carry up to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C 1 -C 8 -alkyl , C 1 -C 8 -haloalkyl, C 1 -C 8 -alkylasulfonyl, C ₃ -C 8 -cycloalkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkylthio, C 1 -C 8 -alkoxy cg-alkylamino, di-C ^ -C-alkyl amino, Cy-cg-alkylaminocarbonyl, di-C - ^ - cg-alkylaminocarbonyl, C ₁ -C-alkylaminotiokarb onyl, di-C 1 -C 8 -alkylaminothiocarbonyl, C ₂ -C 8 -alkenyl, C ₂ -C 8 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetarythio and C (= NO ⁶ ) -A _n -R ⁷ , C ₃ -C -cycloalkyl, C ₃ -C ₆ -cycloalkyloxy, C ₃ -C-cycloalkylthio, C ₃ -C cycloalkylamino, NCJ-Cg-cycloalkyl-NCJ-Cg-alkylamino, C ₃ -C -cycloalkenyl, C ₃ -C-cycloalkenyloxy, C ₃ -C-cycloalkenylthio, C ₃ -C-cycloalkenylamino, NC _{3-Cg-cycloalkenyl-N-C-Cg-alkylamino,} heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-heterocyclyl-NC ^ -C 8 -alkylamino, aryl, arylthio, arylamino, N-aryl-NC 1 -C 8 -alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino, N-hetaryl-NC ₁ -C 8 -alkylamino, wherein the cyclic radicals may be partially or fully halogenated or carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C ₁ -C 8 -alkylsulfonyl, C ₁ -C 8 -alkylsulfonyloxy C ₃ -C-cycloalkyl, C-j-Cg-alkoxy, C ^ -C-haloalkoxy, Cj-Cg-alkoxycarbonyl, C -C alkylthio, C ^ -C-alkyl107 amino, di-C ₁ -CG- alkylamino, C ₁ -C-alkylaminocarbonyl, di-C ^^ - Cg-alkylaminocarbonylamino onyl, C 1 -C 6 -alkylaminothiocarbonyl, di-C 1 -C 6 -alkylaminothiocarbonyl, C ₂ -C 8 -alkenyl, C ₂ -C 8 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R ⁵ represents hydrogen, C 1 -C 6 -alkyl, C 8 -C 8 -cycloalkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 1 -C 10 -alkylcarbonyl, C 2 -C 10 -alkenylcarbonyl, C 3 -C 10 -alkenyl; alkynylcarbonyl or ^{a C -} C 10 -alkylsulfonyl, where the radicals may be partially or fully halogenated or to have attached to them one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C ₁ -CG- alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -alkylsulfonyloxy, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkoxycarbonyl cg-alkylthio, C ^ -C-alkylamino, di-C - ^ - C-alkylainines, C ₁ -C-alkylaminocarbonyl, di-C ^ -C-alkylaminocarbonyl, C ^ -C-alkylaminothiocarbonyl, di-C-Cg- alkylaminothiocarbonyl, C ₂ -C 8 -alkenyl, C ₂ -C 8 -alkenyloxy, C ₃ -C 8 -cycloalkyl, C ₃ -C 8 -cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl and hetaryloxy, wherein cyclic the groups on their side may be partially or fully halogenated or not one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6 -alkylsulfonyloxy, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -alkylthio, C 1 -C 8 -alkylamino, di-C 1 -C 8 -alkylamino, C 1 -C 8 -alkyloxy; -C-alkylaminocarbonyl, di-C ^ -C-alkylaminocarbonyl, C ^ -C-alkylaminothiocarbonyl, di-C - ^ - -alkylaminothiocarbonyl, C ₂ -C alkenyl, C ₂ ~ Cg-alkenyloxy, benzyl, benzyloxy, aryl, , aryloxy, arylthio, hetaryl, hetaryloxy, hetarythio or C (= NOR ⁶ ) -A _n -R ⁷ ; aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, which radicals may be partially or fully halogenated or may be one to 108 the following three groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkyl- alkylsulfonyl, C ₁ -C-alkylsulfonyloxy, C ₃ -C ₆ -cycloalkyl, C ^ -C alkoxy, C - ^ - Cg-haloalkoxy, C ₁ -C -alkoxycarbonyl, C ^ -C alkylthio, C ^^ -C -alkylamino, di-C - ^ - C-amino, C ^ -C-alkylaminocarbonyl, di-C - ^ - Cg-alkylaminocarbonyl, C -alkylaminothiocarbonyl, di-C ₁ -C -alkylaminothiocarbonyl, C ₂ - C 8 -alkenyl, C ₂ -C 8 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy or C (= NOR ⁶ ) -A _n -R ⁷ ; while A represents oxygen, sulfur or nitrogen and nitrogen carries hydrogen or C1-C6-alkyl; n is 0 or 1; Zr R is hydrogen or C1-C6-alkyl and R is hydrogen or C 1 -C 6 -alkyl, and salts thereof. Compounds according to claim 1, in which R ³ , R ⁴ and R ⁵ have the following meanings R ³ is hydrogen, hydroxyl, cyclopropyl, halogen, C? -C? Alkyl, C ₁ -C ₄ -alkoxy or C ₁ ~ C ₄ alkylthio, R ⁴ represents hydrogen, hydroxy, halogen, cyclopropyl, cyclohexyl, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio, aryl or hetaryl, which groups may be partially or fully halogenated or carry one up to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkylsulfonyl, 109 C ₁ -C 8 -alkylsulfonyloxy, C ₃ -C 8 -cycloalkyl, C 1 -C 8 -alkoxy, C ₁ -C 8 -haloalkoxy, C 1 -C 8 -alkoxycarbonyl, C ₁ -C 8 -alkylthio, C 1 -C 8 -alkylamino, di- C ^ -C-alkyl amino, C ^ -C ^ j-alkylaminocarbonyl, di-C - ^ - Cg-alkylaminocarbonyl, C - ^ - C-alkylaminothiocarbonyl, di-C ^ -C-alkylaminothiocarbonyl, _C2 ~ Cg alkenyl, C ₂ -C alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy; R ⁵ is hydrogen, C ₁ -C ₁₀ -alkyl, C ₃ -C 8 -cycloalkyl, C ₂ -C ₁₀ -alkenyl, C ₂ -C ₁₀ -alkynyl, C ₁ -C ₁₀ -alkylcarbonyl, C ₂ -C ₁₀ -alkenylcarbonyl, C ₃ -C ₁₀ -alkynylcarbonyl or C 1 -C 6 -alkylsulfonyl, which radicals may be partially or fully halogenated or carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -alkylsulfonyloxy, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy, C ₁ -C 8 -alkoxy alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -alkylamino; alkylaminothiocarbonyl, di-C 1 -C 8 -alkylaminothiocarbonyl, C ₂ -C 8 -alkenyl, C ₂ -C 8 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarythio, the cyclic groups on their side may be partially or fully halogenated or carry one to three of the following groups: cyano, nitro, hydroxy , mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -alkylsulfonyloxy, C 1 -C 8 -alkoxy, C 1 -C 8 -alkoxy -C -haloalkoxy, C ^ -C alkoxycarbonyl, C ^ -C alkylthio, C ₁ -C -alkylamino, di-C ^ -C alkylamino, C -C-alkylaminocarbonyl, di-C-Cg-alkylaminocarbonyl, C -C 8 -alkylaminothiocarbonyl, di-C 1 -C 8 -alkylaminothiocarbonyl, C ₂ -C 8 -alkenyl, C ₂ -C 8 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarythio or C (= NOR ⁶ ) -A _n -R ⁷ ; Aryl, hetaryl, arylcarbonyl, hetarylcarbonyl, arylsulfonyl or hetarylsulfonyl, wherein these groups may be partially or fully halogenated or carry one to three of the following: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, C 1-4 alkyl; -C-alkyl, C ^^ - Cg haloalkyl, C ^ -C-alkylcarbonyl, C - ^ - Cg-alkylsulfonyl, C -C alkylsulfonyl-trifluoromethanesulfonyloxy, C ₃ -C cycloalkyl, C -C alkoxy, C -C8-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6 alkylaminocarbonyl, C ₁ -C -alkylaminothiocarbonyl, di-C ^^ - -alkylaminothiocarbonyl, _C2 ~ Cg alkenyl, C ₂ -C alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C (= NOR ⁶ ) -A _n -R ⁷ ; while A represents oxygen, sulfur or nitrogen and nitrogen carries hydrogen or C1-C6-alkyl; ₄ n is 0 or 1; 4 R ⁶ represents hydrogen or C 1 -C 6 -alkyl and R ⁷ is hydrogen or C 1 -C 6 -alkyl, and salts thereof. Compounds of formula I according to claim 1, wherein m is 0. ⁴ Compounds of formula I according to claim 1, wherein R ¹ is methyl. 111 A process for the preparation of compounds of the formula I according to claim 1, wherein R ^{3 is} not halogen, characterized in that the benzyl derivative of the formula II (R ² ) is: O = C-SR ¹ (II) wherein L ³ is a nucleophilically replaceable leaving group, reacted with a hydroxyimine of formula III in a manner known per se R ⁵ ON = C (R ⁴ ) - C (R ³ ) = NOH (III) A process for the preparation of compounds of formula I according to claim 1, wherein R ³ and R ⁴ do not represent halogen, characterized in that the benzyl derivative of the formula II is reacted with a dihydroxyimine of the formula IV in a manner known per se. HON = C (R ⁴ ) -C (R ³ ) = NOH (IV) to the compound of formula V (R ² ); HON = C (R ⁴ ) -C (R ³ ) = NOCH ₂ c = noch ₃ 0 = 0 SR ¹ (A) 112 and the compound of formula V then with the compound of formula VI R ⁵ -L ² (VI) wherein L ² represents a nucleophilically exchangeable leaving group, to form a compound of formula I. 7. A method of producing a compound according to claim 1, wherein R s ^J does not represent a halogen atom, characterized in that a benzyl derivative of the formula II according to claim 5 is reacted in known manner with karbonylhydroxyiminoderivátom VIIa O = C (R ⁴ ) -C (R ³ ) = NHO (VIIa) to the compound of formula VIII (r ² : O = C (R ⁴ ) -C (r 1) = NOCH ₂ c = noch ₃ O = C-SR ¹ (VIII) and the compound of formula VIII is then a) first with hydroxylamine or a salt thereof and then with a compound of formula VI R ⁵ -L ⁵ (VI) according to claim 6, or b) with hydroxylamine or an ammonium salt of hydroxylamine of formula IXa or IXb, respectively 113 y ⁵ -onh ₂ (ixa) R ⁵ -ONH ₃ ⁺ Q "(IXb) wherein Q is an acid anion, is reacted to a compound of formula I. A composition for controlling animal pests or harmful fungi comprising: conventional additives and an effective amount of a compound of formula (I) according to claim 1. A method of controlling animal pests and harmful fungi, characterized in that the pests or harmful fungi, their habitat or plants, the areas, materials or compartments that are disposed of are treated with an effective amount of a compound of formula I according to claim 1. .y J « Use of compounds to produce a preparation of fungi. of the formula I as claimed in claim 1 against animal pests and harmful Use of compounds of the formula I according to claim 1 for controlling animal pests and harmful fungi. Compounds of formula VIII according to claim 7. Use of compounds of formula VIII according to claim 7 as intermediates.