Heterocyclic substituted 4-benzoyl-pyrazole as herbicides

This application is a 371 of PCT/EP98/04635 Jul. 23, 1998 now WO 99/10328 Mar. 4, 1999.

The present invention relates to substituted 4-benzoylpyrazoles of the formula I

which is attached in position 4 and where

R

4

is hydrogen, C

1

-C

6

-alkyl or C

1

-C

6

-haloalkyl;

R

5

is C

1

-C

6

-alkyl, C

1

-C

6

-haloalkyl, phenyl or phenyl which may be partially or fully halogenated and/or may carry one to three of the following radicals:

nitro, cyano, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy;

R

6

is hydrogen, C

1

-C

6

-alkyl, C

1

-C

6

-haloalkyl, C

1

-C

6

-alkylcarbonyl, C

1

-C

6

-haloalkylcarbonyl, C

1

-C

6

-alkoxycarbonyl, C

1

-C

6

-alkylsulfonyl, C

1

-C

6

-haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl, phenoxycarbonyl or phenylsulfonyl,

where the four last-mentioned substituents are unsubstituted, or the phenyl ring in question may be partially or fully halogenated and/or may carry one to three of the following radicals:

nitro, cyano, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy;

X

1

is a straight-chain or branched C

1

-C

6

-alkylene, a C

2

-C

6

-alkenylene or a C

2

-C

6

-alkynylene chain which is interrupted by a hetero atom selected from the group consisting of:

oxygen and sulfur,

where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR

7

, —OCOR

7

, —OCONHR

7

or —OSO

2

R

7

;

R

7

is hydrogen, C

1

-C

6

-alkyl, C

2

-C

6

-alkenyl, C

2

-C

6

-alkynyl, phenyl, phenyl-C

1

-C

6

-alkyl, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may be substituted by one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy;

Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R

8

;

R

8

is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals:

cyano, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy;

and agriculturally useful salts thereof.

In addition, the invention relates to processes and intermediates for preparing compounds of the formula I, to compositions comprising them, and to the use of the compounds of the formula I and of compositions comprising them for controlling harmful plants.

4-Benzoylpyrazoles are disclosed in the literature, for example in EP-A 282 944.

However, the herbicidal properties of the prior art compounds and their crop plant safety are not entirely satisfactory.

It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.

We have found this object is achieved by the 4-benzoylpyrazoles of the formula I according to the invention and their herbicidal activity.

Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.

The present invention also provides stereoisomers of the compounds of the formula I. Pure stereoisomers and also mixtures thereof are included.

Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers and, if this is the case, are present as enantiomers or mixtures of diastereomers. The invention provides the pure enantiomers or diastereomers and also mixtures thereof.

The compounds of the formula I may also be present in the form of their agriculturally useful salts, the kind of salt generally not being important. The salts of those cations or the acid addition salts of those acids whose cations or anions, respectively, do not adversely affect the herbicidal activity of the compounds I are generally suitable.

Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where, if desired, one to four hydrogen atoms may be replaced by C

1

-C

4

-alkyl or hydroxyl-C

1

-C

4

-alkyl and/or one phenyl or benzyl, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C

1

-C

4

-alkyl)sulfonium and sulfoxonium ions, preferably tri(C

1

-C

4

-alkyl)sulfoxonium.

Anions of useable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C

1

-C

4

-alkanoic acids, preferably formate, acetate, propionate and butyrate.

Process A:

Reactions of pyrazoles of the formula II (where R

6

=H) with an activated carboxylic acid IIIa or a carboxylic acid IIIb, which is preferably activated in situ, to give the acylation product V, and subsequent rearrangements to the compounds of the formula Ia according to the invention.

L

1

is a nucleophilically replaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, or carboxylate, for example acetate, trifluoroacetate, etc.

The activated carboxylic acid can be employed directly, as in the case of the acyl halides, or be generated in situ, for example by using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic esters, 2-pyridine disulfite/triphenylphosphine, carbonyldiimidazole, etc.

It may be advantageous to carry out the acylation reaction in the presence of a base. The starting materials and the auxiliary base are advantageously employed in equimolar amounts. A slight excess of auxiliary base, for example 1.2 to 1.5 molar equivalents, based on II, may be advantageous under certain circumstances.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Examples of solvents which can be used are chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters such as ethyl acetate or mixtures of these.

If acyl halides are employed as activated carboxylic acid component, it may be advantageous to cool the reaction mixture to 0-10° C. when adding this reaction partner. The mixture is subsequently stirred at 20-100° C., preferably at 25-50° C., until the reaction is complete. Work-up is carried out in the customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are particularly suitable for this purpose are methylene chloride, diethyl ether and ethyl acetate. After the organic phase has been dried and the solvent has been removed, the crude enol ester of the formula V is purified, preferably by chromatography. Alternatively, it is possible to employ the crude enol ester of the formula V without further purification for the rearrangement reaction.

The rearrangement of the enol esters of the formula V to the compounds of the formula I is advantageously carried out at from 20 to 40° C. in a solvent and in the presence of a base and, if appropriate, in the presence of a cyano compound.

Examples of solvents which can be used are acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines such as triethylamine, pyridine or alkali metal carbonates, such as sodium carbonate, potassium carbonate, which are preferably employed in equimolar amounts or up to a four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonates.

Suitable cyano compounds are inorganic cyanides such as sodium cyanide, potassium cyanide and organic cyano compounds such as acetone cyanohydrin, trimethylsilyl cyanide. They are employed in an amount of 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example, in an amount of 5 to 15, preferably 10, mol percent, based on the ester.

Particular preference is given to employing alkali metal carbonates, such as potassium carbonate, in acetonitrile or dioxane.

Work-up can be carried out in a manner known per se. For example, the reaction mixture is acidified with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride, ethyl acetate. The organic phase can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified, and the precipitate which forms is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.

(Examples of the synthesis of esters from hydroxypyrazoles and the rearrangement of the esters are mentioned for example in EP-A 282 944 or U.S. Pat No. 4, 643, 757).

The pyrazoles of the formula II (where R

6

=H) used as starting materials are known or can be prepared by methods known per se (for example EP-A 240 001, J. Prakt. Chem. 315 (1973), 383).

Process B:

Reactions of 4-benzoylpyrazoles of the formula Ia with a compound of the formula IV (where R

6

≠H):

L

2

is a nucleophilically replaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, sulfonate, for example mesylate, triflate, etc.

The compounds of the formula IV can be employed directly, for example in the case of the alkyl halides, acyl halides, sulfonyl halides, carboxylic anhydrides and sulfonic anhydrides, or prepared in situ, for example activated carboxylic acids (by means of carboxylic acid and dicyclohexylcarbodiimide, carbonyldiimidazole, etc.).

In general, the starting materials are employed in an equimolar ratio. However, it may also be advantageous to employ an excess of one or the other component.

Where appropriate, it may be advantageous to carry out the reaction in the presence of a base. The starting materials and the auxiliary base are advantageously employed in equimolar amounts. Under certain circumstances, it may be advantageous to employ an excess of the auxiliary base, for example 1.5 to 3 molar equivalents, based on Ia.

Suitable auxiliary bases are tertiary alkylamines such as triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate, potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine, pyridine and potassium carbonate.

Examples of suitable solvents are chlorinated hydrocarbons such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide or esters, such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range of from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in a manner known per se.

The benzoic acids of the formula III are novel,

where:

R

1

and R

2

are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C

1

-C

6

-alkyl, C

1

-C

6

-haloalkyl, C

1

-C

6

-alkoxy-C

1

-C

6

-alkyl, C

2

-C

6

-alkenyl, C

2

-C

6

-alkynyl, —OR

3

, —OCOR

3

, —OSO

2

R

3

, —S(O)

n

R

3

, —SO

2

OR

3

, —SO

2

N(R

3

)

2

, —NR

3

SO

2

R

3

or —NR

3

COR

3

;

n is 0, 1 or 2;

R

3

is hydrogen, C

1

-C

6

-alkyl, C

1

-C

6

-haloalkyl, C

2

-C

6

-alkenyl, C

2

-C

6

-alkynyl, phenyl or phenyl-C

1

-C

6

-alkyl; where the abovementioned alkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R

3

, —OR

3

, —SR

3

, —N(R

3

)

2

, ═NOR

3

, —OCOR

3

, —SCOR

3

, —NR

3

COR

3

, —CO

2

R

3

, —COSR

3

, —CON(R

3

)

2

, C

1

-C

4

-alkyliminooxy, C

1

-C

4

-alkoxyamino, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkoxy-C

2

-C

6

-alkoxycarbonyl, C

1

-C

4

-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted;

X

1

is a straight-chain or branched C

1

-C

6

-alkylene, a C

2

-C

6

-alkenylene or a C

2

-C

6

-alkynylene chain which is interrupted by a hetero atom selected from the group consisting of:

oxygen and sulfur,

where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR

7

, —OCOR

7

, —OCONHR

7

or —OSO

2

R

7

;

R

7

is hydrogen, C

1

-C

6

-alkyl, C

2

-C

6

-alkenyl, C

2

-C

6

-alkynyl, phenyl, phenyl-C

1

-C

6

-alkyl, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may be substituted by one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy;

Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R

8

;

R

8

is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals:

cyano, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy;

R

9

is hydroxyl or a hydrolyzable radical.

Examples of hydrolyzable radicals are alkoxy, phenoxy, alkylthio and phenylthio radicals which can be substituted, halides, hetaryl radicals which are bonded via nitrogen, amino and imino radicals which can be substituted, etc.

Preference is given to benzoyl halides IIIa where L

1

=halogen ({circumflex over (=)} III where R

9

=halogen),

where the variables R

1

, R

2

, X

1

and Het are each as defined under formula III and

L

1

is halogen, in particular chlorine or bromine.

Preference is also given to benzoic acids of the formula IIIb ({circumflex over (=)} III where R

9

=hydroxyl),

where the variables R

1

, R

2

, X

1

and Het are each as defined under formula III.

Preference is also given to benzoic esters of the formula IIIc ({circumflex over (=)} III where R

9

=C

1

-C

6

-alkoxy),

where the variables R

1

, R

2

, X

1

and Het are each as defined under formula III and

M is C

1

-C

6

-alkoxy.

The compounds of the formula IIIa (where L

1

=halogen) can be synthesized by methods similar to those known from the literature (cf. L. G. Fieser, M. Fieser “Reagents for Organic Synthesis”, Vol. I, pp. 767-769 (1967)) by reacting benzoic acids of the formula IIIb with halogenating agents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride and oxalyl bromide.

The benzoic acids of the formula IIIb can be obtained, inter alia, by hydrolyzing the benzoic esters of the formula IIIc (where M=C

1

-C

6

-alkoxy).

The benzoic esters of the formula IIIc according to the invention can be synthesized by various methods known from the literature (for example a: G. Dittus in Houben-Weyl, Methoden der Organischen Chemie, Volume VI/3, Oxygen Compounds I, 4th Edition, 1965, p. 493 ff., Georg Thieme Verlag; b: T. L. Gilchrist, Heterocyclenchemie, 2nd Edition, Verlag Chemie, 1995), as illustrated in the examples that follow.

Process C:

Substitution of the benzoic esters VIa with suitable nucleophiles VII gives the benzoic esters IIIc according to the invention,

where M, R

1

and R

2

are each as defined above, L

2

is a suitable nucleophilically replaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, sulfonate, for example mesylate, triflate, etc.

X

2

is a straight-chain or branched alkylene, an alkenylene or an alkynylene chain having at least one and a maximum of five carbon atoms, where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR

7

, —OCOR

7

, —OCONHR

7

or —OSO

2

R

7

and

X

3

is a straight-chain or branched alkylene, an alkenylene or an alkynylene chain having a maximum of five carbon atoms, where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR

7

, —OCOR

7

, —OCONHR

7

or —OSO

2

R

7

.

The starting materials are usually employed in equimolar amounts. However, it may be advantageous to employ one or the other component in excess.

If appropriate, it may be advantageous to carry out the reaction in the presence of a base. The starting materials and the auxiliary base are advantageously employed in equimolar amounts. In certain cases, an excess of the auxiliary base, for example 1.5 to 3 molar equivalents, based on VIII, may be advantageous.

Suitable auxiliary bases are tertiary alkylamines such as triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine, pyridine and potassium carbonate.

Suitable solvents are, for example, chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in a manner known per se.

Emphasis is to be given to compounds of the formula I according to the invention where the group X

1

is a C

1

-C

3

-alkylene, a C

2

-C

3

-alkenylene or C

2

-C

3

-alkynylene chain which is interrupted by an oxygen atom and

Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R

8

.

Furthermore, emphasis is to be given to the compounds of the formula I according to the invention where the group Het is a five- or six-membered partially or fully saturated heterocyclic or a five- or six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen;

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or substituted by RB;

R

8

is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals:

cyano, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy.

The organic moieties mentioned for the substituents R

1

-R

9

or as radicals on phenyl, hetaryl and heterocyclyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, ie. all alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, alkyliminooxy, alkoxyamino, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, alkenyl, cycloalkenyl, alkynyl moieties can be straight-chain or branched. Unless otherwise specified, halogenated substituents preferably carry one to five identical or different halogen atoms, the meaning of halogen being in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C

1

-C

4

-alkyl, and the alkyl moieties of C

1

-C

4

-alkylcarbonyl: methyl, ethyl, n-propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;

C

1

-C

6

-alkyl and the alkyl moieties of C

1

-C

6

-alkoxy-C

1

-C

6

-alkyl and C

1

-C

6

-alkylcarbonyl: C

1

-C

4

-alkyl as mentioned above, and also 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-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;

C

1

-C

4

-haloalkyl: a C

1

-C

4

-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, eg. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 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, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;

C

1

-C

6

-haloalkyl and the haloalkyl moieties of C

1

-C

6

-haloalkylcarbonyl: C

1

-C

4

-haloalkyl as mentioned above, and also 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;

C

1

-C

4

-alkoxy and the alkoxy moieties of C

1

-C

4

-alkoxyamino, C

1

-C

4

-alkoxy-C

2

-C

6

-alkoxycarbonyl and C

1

-C

4

-alkoxycarbonyl: methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

C

1

-C

6

-alkoxy and the alkoxy moieties of C

1

-C

6

-alkoxy-C

1

-C

6

-alkyl, C

1

-C

6

-alkoxy-C

2

-C

6

-alkyl, C

1

-C

4

-alkoxy-C

2

-C

6

-alkoxycarbonyl and C

1

-C

6

-alkoxycarbonyl: C

1

-C

4

-alkoxy as mentioned above, and also pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;

C

1

-C

4

-haloalkoxy: a C

1

-C

4

-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, eg. fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;

C

1

-C

4

-alkylsulfonyl (C

1

-C

4

-alkyl-S(═O)

2

—): methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;

C

1

-C

6

-alkylsulfonyl: C

1

-C

4

-alkylsulfonyl as mentioned above, and also pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C

1

-C

6

-haloalkylsulfonyl: a C

1

-C

6

-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, ie. fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(choromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl and dodecafluorohexylsulfonyl;

C

1

-C

4

-alkyliminooxy: methyliminooxy, ethyliminooxy, 1-propyliminooxy, 2-propyliminooxy, 1-butyliminooxy and 2-butyliminooxy;

C

3

-C

6

-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl;

C

2

-C

6

-alkenyl: C

3

-C

6

-alkenyl as mentioned above, and also ethenyl;

C

3

-C

6

-alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn-1-yl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-1-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl and 4-methylpent-2-yn-5-yl;

C

2

-C

6

-alkynyl: C

3

-C

6

-alkynyl as mentioned above, and also ethynyl:

C

3

-C

6

-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C

4

-C

6

-cycloalkenyl: cyclobuten-1-yl, cyclobuten-3-yl, cyclopenten-1-yl, cyclopenten-3-yl, cyclopenten-4-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl;

heterocyclyl, and also the heterocyclyl radicals in heterocyclyloxy: three- to seven-membered saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three hetero atoms selected from a group consisting of oxygen, nitrogen and sulfur, such as oxiranyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-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-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,3-dihydrofuran-4-yl, 2,3-dihydrofuran-5-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-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-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydropyrazol-3-yl, 2,5-dihydropyrazol-4-yl, 2,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-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-dithian-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2-yl,

hetaryl, and also the hetaryl radicals in hetaryloxy: aromatic mono- or polycyclic radicals which, besides carbon ring members, may additionally 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, eg. 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, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 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, 1,2,4,5-tetrazin-3-yl, and also the corresponding benzo-fused derivatives.

All phenyl, hetaryl and heterocyclyl rings are preferably unsubstituted or carry one to three halogen atoms and/or one or two radicals selected from the following group: nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy and methoxycarbonyl.

With a view to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meanings, viz. in each case alone or in combination:

R

1

is nitro, halogen, cyano, thiocyanato, C

1

-C

6

-alkyl, C

1

-C

6

-haloalkyl, C

1

-C

6

-alkoxy-C

1

-C

6

-alkyl, C

2

-C

6

-alkenyl, C

2

-C

6

-alkynyl, —OR

3

or —S(O)

n

R

3

;

particularly preferably nitro, halogen such as, for example, fluorine, chlorine or bromine, C

1

-C

6

-haloalkyl, —OR

3

or —SO

2

R

3

;

R

2

is hydrogen, nitro, halogen, cyano, thiocyanato, C

1

-C

6

-alkyl, C

1

-C

6

-haloalkyl, C

1

-C

6

-alkoxy-C

1

-C

6

-alkyl, C

2

-C

6

-alkenyl, C

2

-C

6

-alkynyl, —OR

3

or —S(O)

n

R

3

;

particularly preferably hydrogen, nitro, halogen such as, for example, fluorine, chlorine or bromine, C

1

-C

6

-alkyl, C

1

-C

6

-haloalkyl, —OR

3

or —SO

2

R

3

;

n is 0, 1 or 2, particularly preferably 0 or 2;

R

3

is hydrogen, C

1

-C

6

-alkyl, C

1

-C

6

-haloalkyl, C

2

-C

6

-alkenyl, C

2

-C

6

-alkynyl, phenyl or phenyl-C

1

-C

6

-alkyl; particularly preferably hydrogen, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

2

-C

3

-alkenyl, C

2

-C

3

-alkynyl or phenyl; where the abovementioned alkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R

3

, —OR

3

, —SR

3

, —N(R

3

)

2

, ═NOR

3

, —OCOR

3

, —SCOR

3

, —NR

3

COR

3

, —CO

2

R

3

, —COSR

3

, —CON(R

3

)

2

, C

1

-C

4

-alkyliminooxy, C

1

-C

4

-alkoxyamino, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkoxy-C

2

-C

6

-alkoxycarbonyl, C

1

-C

4

-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted;

R

4

is hydrogen, C

1

-C

6

-alkyl or C

1

-C

6

-haloalkyl; particularly preferably hydrogen, methyl, ethyl or trifluoromethyl;

R

5

is C

1

-C

6

-alkyl or C

1

-C

6

-haloalkyl; particularly preferably methyl, ethyl, propyl, isopropyl, butyl or isobutyl;

R

6

is hydrogen, C

1

-C

6

-alkyl, C

1

-C

6

-alkylcarbonyl, C

1

-C

6

-haloalkylcarbonyl, C

1

-C

6

-alkoxycarbonyl, C

1

-C

6

-alkylsulfonyl, C

1

-C

6

-haloalkylsulfonyl, phenylcarbonylmethyl, or phenylsulfonyl, where the phenyl ring of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy;

X

1

is a straight-chain or branched C

1

-C

4

-alkylene, a C

2

-C

4

-alkenylene or a C

2

-C

4

-alkynylene chain, particularly preferably an ethylene, propylene, propenylene or propynylene chain which is interrupted by a hetero atom selected from the group consisting of

oxygen and sulfur, preferably oxygen,

where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR

7

, —OCOR

7

, —OCONHR

7

or —OSO

2

R

7

;

R

7

is hydrogen, C

1

-C

4

-alkyl, C

2

-C

4

-alkenyl, C

2

-C

4

-alkynyl, phenyl, phenyl-C

1

-C

4

-alkyl, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may be substituted by one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy;

Het is a three- to six-membered, preferably a five- or six-membered, partially or fully saturated heterocyclic group or a three- to six-membered, preferably five- or six-membered, heteroaromatic group having up to three hetero atoms, particularly preferably having one or two hetero atoms, selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

particularly preferably from the following two groups:

nitrogen or

oxygen in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R

8

;

R

8

is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals:

cyano, formyl, C

1

-C

4

-alkylamino, C

1

-C

4

-dialkylamino, C

1

-C

4

-alkoxycarbonyl, C

1

-C

4

-alkylcarbonyl, C

1

-C

4

-alkylcarbonyloxy, C

1

-C

4

-alkyl, C

1

-C

4

-haloalkyl, C

1

-C

4

-alkylthio, C

1

-C

4

-haloalkylthio, C

1

-C

4

-alkoxy, C

1

-C

4

-haloalkoxy.

Particular preference is given to the compounds of the formula Ia where R

1

is bonded in position 2 and R

2

is bonded in position 4 of the phenyl ring.

Most particular preference is given to the compounds of the formula Ia where the substituents R

1

and R

2

and Q are each as defined above, X

1

is a C

1

-C

3

-alkylene, a C

2

-C

3

-alkenylene or C

2

-C

3

-alkynylene chain which is interrupted by an oxygen atom and

Het is a three- to six-membered, preferably a five- or six-membered, partially or fully saturated heterocyclic group or a three- to six-membered, preferably five- or six-membered, heteroaromatic group having up to three hetero atoms, particularly preferably having one or two hetero atoms, selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

particularly preferably from the following two groups:

nitrogen or

oxygen in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R

8

.

Furthermore, most particular preference is given to the compounds of the formula Ia according to the invention where the substituents R

1

, R

2

and X

1

are each as defined above and Het is a five- or six-membered partially or fully saturated heterocyclic group or a five- or six-membered heteroaromatic group having up to three hetero atoms, particularly preferably having one or two hetero atoms, selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

particularly preferably from the following two groups:

nitrogen or

oxygen in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R

8

.

Particular preference is given to the compounds Ib of Tables 1 to 144.

TABLE A

No.

X

1

Het

1

OCH

2

oxiranyl

2

OCH

2

3-methyl-2-oxiranyl

3

OCH

2

2-oxetanyl

4

OCH

2

3-hydroxy-3-methyl-2-oxetanyl

5

OCH

2

3-hydroxy-3-ethyl-2-oxetanyl

6

OCH

2

3-hydroxy-3-propyl-2-oxetanyl

7

OCH

2

3-hydroxy-3-butyl-2-oxetanyl

8

OCH

2

3-methoxy-3-methyl-2-oxetanyl

9

OCH

2

3-methoxy-3-ethyl-2-oxetanyl

10

OCH

2

3-methoxy-3-propyl-2-oxetanyl

11

OCH

2

3-methoxy-3-butyl-2-oxetanyl

12

OCH

2

3-trimethyl-

silyloxy-3-methyl-2-oxetanyl

13

OCH

2

3-trimethyl-

silyloxy-3-ethyl-2-oxetanyl

14

OCH

2

3-trimethyl-

silyloxy-3-propyl-2-oxetanyl

15

OCH

2

3-trimethyl-

silyloxy-3-butyl-2-oxetanyl

16

OCH

2

3-oxetanyl

17

OCH

2

2-furyl

18

OCH

2

4,5-dihydro-2-furyl

19

OCH

2

2,3-dihydro-2-furyl

20

OCH

2

3-furyl

21

OCH

2

4,5-dihydro-3-furyl

22

OCH

2

2,3-dihydro-3-furyl

23

OCH

2

2-thienyl

24

OCH

2

4,5-dihydro-2-thienyl

25

OCH

2

2,3-dihydro-2-thienyl

26

OCH

2

5-chloro-2-thienyl

27

OCH

2

5-methyl-2-thienyl

28

OCH

2

3-thienyl

29

OCH

2

4,5-dihydro-3-thienyl

30

OCH

2

2,3-dihydro-3-thienyl

31

OCH

2

2-pyrrolyl

32

OCH

2

2,5-dihydro-2-pyrrolyl

33

OCH

2

3-pyrrolyl

34

OCH

2

2,5-dihydro-3-pyrrolyl

35

OCH

2

3-isoxazolyl

36

OCH

2

4-methyl-3-isoxazolyl

37

OCH

2

5-methyl-3-isoxazolyl

38

OCH

2

4,5-dimethyl-3-isoxazolyl

39

OCH

2

4,5-dihydro-3-isoxazolyl

40

OCH

2

4-methyl-4,5-dihydro-3-isoxazolyl

41

OCH

2

5-methyl-4,5-dihydro-3-isoxazolyl

42

OCH

2

4,5-dimethyl-4,5-dihydro-3-isoxazo-

lyl

43

OCH

2

4-isoxazolyl

44

OCH

2

3-methyl-4-isoxazolyl

45

OCH

2

5-methyl-4-isoxazolyl

46

OCH

2

5-cyclopropyl-4-isoxazolyl

47

OCH

2

5-phenyl-4-isoxazolyl

48

OCH

2

3,5-dimethyl-4-isoxazolyl

49

OCH

2

4,5-dihydro-4-isoxazolyl

50

OCH

2

3-methyl-4,5-dihydro-4-isoxazolyl

51

OCH

2

5-methyl-4,5-dihydro-4-isoxazolyl

52

OCH

2

3,5-dimethyl-4,5-dihydro-4-isoxazo-

lyl

53

OCH

2

5-isoxazolyl

54

OCH

2

3-methyl-5-isoxazolyl

55

OCH

2

4-methyl-5-isoxazolyl

56

OCH

2

3,4-dimethyl-5-isoxazolyl

57

OCH

2

4,5-dihydro-5-isoxazolyl

58

OCH

2

3-methyl-4,5-dihydro-5-isoxazolyl

59

OCH

2

4-methyl-4,5-dihydro-5-isoxazolyl

60

OCH

2

3,4-dimethyl-4,5-dihydro-5-isoxazo-

lyl

61

OCH

2

3-isothiazolyl

62

OCH

2

4-methyl-3-isothiazolyl

63

OCH

2

5-methyl-3-isothiazolyl

64

OCH

2

4-isothiazolyl

65

OCH

2

3-methyl-4-isothiazolyl

66

OCH

2

5-methyl-4-isothiazolyl

67

OCH

2

5-isothiazolyl

68

OCH

2

3-methyl-5-isothiazolyl

69

OCH

2

4-methyl-5-isothiazolyl

70

OCH

2

2-oxazolyl

71

OCH

2

4-oxazolyl

72

OCH

2

5-oxazolyl

73

OCH

2

2-thiazolyl

74

OCH

2

4-thiazolyl

75

OCH

2

5-thiazolyl

76

OCH

2

3-pyrazolyl

77

OCH

2

4-pyrazolyl

78

OCH

2

1-methyl-3-pyrazolyl

79

OCH

2

1-methyl-4-pyrazolyl

80

OCH

2

1-methyl-5-pyrazolyl

81

OCH

2

2-imidazolyl

82

OCH

2

1-methyl-2-imidazolyl

83

OCH

2

5-methyl-[1,3,4]-2-oxadiazolyl

84

OCH

2

5-methyl-[1,2,4]-3-oxadiazolyl

85

OCH

2

5-methyl-[1,3,4]-2-thiadiazolyl

86

OCH

2

5-methyl-[1,2,4]-3-thiadiazolyl

87

OCH

2

[1,2,4]-3-triazolyl

88

OCH

2

[1,2,3]-4-triazolyl

89

OCH

2

2-pyridyl

90

OCH

2

6-chloro-2-pyridyl

91

OCH

2

6-methoxy-2-pyridyl

92

OCH

2

6-trifluoromethyl-2-pyridyl

93

OCH

2

3-pyridyl

94

OCH

2

2-chloro-3-pyridyl

95

OCH

2

2-methoxy-3-pyridyl

96

OCH

2

4-pyridyl

97

OCH

2

2-chloro-4-pyridyl

98

OCH

2

2-methoxy-4-pyridyl

99

OCH

2

2-ethoxy-4-pyridyl

100

OCH

2

2-methylthio-4-pyridyl

101

OCH

2

2-trifluoromethyl-5-pyridyl

102

OCH

2

2-pyrimidinyl

103

OCH

2

3-pyrimidinyl

104

OCH

2

4-pyrimidinyl

105

OCH

2

2-pyrazinyl

106

OCH

2

3-pyridazinyl

107

OCH

2

4-pyridazinyl

108

OCH

2

2-(2H-1,3-oxazinyl)

109

OCH

2

2-(6H-1,3-oxazinyl)

110

OCH

2

4-(6H-1,3-oxazinyl)

111

OCH

2

6-(6H-1,3-oxazinyl)

112

OCH

2

[1,3,5]-2-triazinyl

113

OCH

2

[1,2,4]-3-triazinyl

114

OCH

2

[1,2,4]-5-triazinyl

115

OCH

2

[1,2,4]-6-triazinyl

116

oxiranyl

117

3-methyl-2-oxiranyl

118

2-oxetanyl

119

3-hydroxy-3-methyl-2-oxetanyl

120

3-hydroxy-3-ethyl-2-oxetanyl

121

3-hydroxy-3-propyl-2-oxetanyl

122

3-hydroxy-3-butyl-2-oxetanyl

123

3-methoxy-3-methyl-2-oxetanyl

124

3-methoxy-3-ethyl-2-oxetanyl

125

3-methoxy-3-propyl-2-oxetanyl

126

3-methoxy-3-butyl-2-oxetanyl

127

3-trimethyl-

silyloxy-3-methyl-2-oxetanyl

128

3- trimethyl-

silyloxy-3-ethyl-2-oxetanyl

129

3-trimethyl-

silyloxy-3-propyl-2-oxetanyl

130

3-trimethyl-

silyloxy-3-butyl-2-oxetanyl

131

3-oxetanyl

132

2-furyl

133

4,5-dihydro-2-furyl

134

2,3-dihydro-2-furyl

135

3-furyl

136

4,5-dihydro-3-furyl

137

2,3-dihydro-3-furyl

138

2-thienyl

139

CH

2

O

4,5-dihydro-2-thienyl

140

CH

2

O

2,3-dihydro-2-thienyl

141

CH

2

O

5-chloro-2-thienyl

142

CH

2

O

5-methyl-2-thienyl

143

CH

2

O

3-thienyl

144

CH

2

O

4,5-dihydro-3-thienyl

145

CH

2

O

2,3-dihydro-3-thienyl

146

CH

2

O

2-pyrrolyl

147

CH

2

O

2,5-dihydro-2-pyrrolyl

148

CH

2

O

3-pyrrolyl

149

CH

2

O

2,5-dihydro-3-pyrrolyl

150

CH

2

O

3-isoxazolyl

151

CH

2

O

4-methyl-3-isoxazolyl

152

CH

2

O

5-methyl-3-isoxazolyl

153

CH

2

O

4,5-dimethyl-3-isoxazolyl

154

CH

2

O

4,5-dihydro-3-isoxazolyl

155

CH

2

O

4-methyl-4,5-dihydro-3-isoxazolyl

156

CH

2

O

5-methyl-4,5-dihydro-3-isoxazolyl

157

CH

2

O

4,5-dimethyl-4,5-dihydro-3-isoxazo-

lyl

158

CH

2

O

4-isoxazolyl

159

CH

2

O

3-methyl-4-isoxazolyl

160

CH

2

O

5-methyl-4-isoxazolyl

161

CH

2

O

5-cyclopropyl-4-isoxazolyl

162

CH

2

O

5-phenyl-4-isoxazolyl

163

CH

2

O

3,5-dimethyl-4-isoxazolyl

164

CH

2

O

4,5-dihydro-4-isoxazolyl

165

CH

2

O

3-methyl-4,5-dihydro-4-isoxazolyl

166

CH

2

O

5-methyl-4,5-dihydro-4-isoxazolyl

167

CH

2

O

3,5-dimethyl-4,5-dihydro-4-isoxazo-

lyl

168

CH

2

O

5-isoxazolyl

169

CH

2

O

3-methyl-5-isoxazolyl

170

CH

2

O

4-methyl-5-isoxazolyl

171

CH

2

O

3,4-dimethyl-5-isoxazolyl

172

CH

2

O

4,5-dihydro-5-isoxazolyl

173

CH

2

O

3-methyl-4,5-dihydro-5-isoxazolyl

174

CH

2

O

4-methyl-4,5-dihydro-5-isoxazolyl

175

CH

2

O

3,4-dimethyl-4,5-dihydro-5-isoxazo-

lyl

176

CH

2

O

3-isothiazolyl

177

CH

2

O

4-methyl-3-isothiazolyl

178

CH

2

O

5-methyl-3-isothiazolyl

179

CH

2

O

4-isothiazolyl

180

CH

2

O

3-methyl-4-isothiazolyl

181

CH

2

O

5-methyl-4-isothiazolyl

182

CH

2

O

5-isothiazolyl

183

CH

2

O

3-methyl-5-isothiazolyl

184

CH

2

O

4-methyl-5-isothiazolyl

185

CH

2

O

2-oxazolyl

186

CH

2

O

4-oxazolyl

187

CH

2

O

5-oxazolyl

188

CH

2

O

2-thiazolyl

189

CH

2

O

4-thiazolyl

190

CH

2

O

5-thiazolyl

191

CH

2

O

3-pyrazolyl

192

CH

2

O

4-pyrazolyl

193

CH

2

O

1-methyl-3-pyrazolyl

194

CH

2

O

1-methyl-4-pyrazolyl

195

CH

2

O

1-methyl-5-pyrazolyl

196

CH

2

O

2-imidazolyl

197

CH

2

O

1-methyl-2-imidazolyl

198

CH

2

O

5-methyl-[1,3,4]-2-oxadiazolyl

199

CH

2

O

5-methyl-[1,2,4]-3-oxadiazolyl

200

CH

2

O

5-methyl-[1,3,4]-2-thiadiazolyl

201

CH

2

O

5-methyl-[1,2,4]-3-thiadiazolyl

202

CH

2

O

[1,2,4]-3-triazolyl

203

CH

2

O

[1,2,3]-4-triazolyl

204

CH

2

O

2-pyridyl

205

CH

2

O

6-chloro-2-pyridyl

206

CH

2

O

6-methoxy-2-pyridyl

207

CH

2

O

6-trifluoromethyl-2-pyridyl

208

CH

2

O

3-pyridyl

209

CH

2

O

2-chloro-3-pyridyl

210

CH

2

O

2-methoxy-3-pyridyl

211

CH

2

O

4-pyridyl

212

CH

2

O

2-chloro-4-pyridyl

213

CH

2

O

2-methoxy-4-pyridyl

214

CH

2

O

2-ethoxy-4-pyridyl

215

CH

2

O

2-methylthio-4-pyridyl

216

CH

2

O

2-trifluoromethyl-5-pyridyl

217

CH

2

O

2-pyrimidinyl

218

CH

2

O

3-pyrimidinyl

219

CH

2

O

4-pyrimidinyl

220

CH

2

O

2-pyrazinyl

221

CH

2

O

3-pyridazinyl

222

CH

2

O

4-pyridazinyl

223

CH

2

O

2-(2H-1,3-oxazinyl)

224

CH

2

O

2-(6H-1,3-oxazinyl)

225

CH

2

O

4-(6H-1,3-oxazinyl)

226

CH

2

O

6-(6H-1,3-oxazinyl)

227

CH

2

O

[1,3,5]-2-triazinyl

228

CH

2

O

[1,2,4]-3-triazinyl

229

CH

2

O

[1,2,4]-5-triazinyl

230

CH

2

O

[1,2,4]-6-triazinyl

231

OCH

2

CH

2

oxiranyl

232

OCH

2

CH

2

3-methyl-2-oxiranyl

233

OCH

2

CH

2

2-oxetanyl

234

OCH

2

CH

2

3-hydroxy-3-methyl-2-oxetanyl

235

OCH

2

CH

2

3-hydroxy-3-ethyl-2-oxetanyl

236

OCH

2

CH

2

3-hydroxy-3-propyl-2-oxetanyl

237

OCH

2

CH

2

3-hydroxy-3-butyl-2-oxetanyl

238

OCH

2

CH

2

3-methoxy-3-methyl-2-oxetanyl

239

OCH

2

CH

2

3-methoxy-3-ethyl-2-oxetanyl

240

OCH

2

CH

2

3-methoxy-3-propyl-2-oxetanyl

241

OCH

2

CH

2

3-methoxy-3-butyl-2-oxetanyl

242

OCH

2

CH

2

3-trimethyl-

silyloxy-3-methyl-2-oxetanyl

243

OCH

2

CH

2

3-trimethyl-

silyloxy-3-ethyl-2-oxetanyl

244

OCH

2

CH

2

3-trimethyl-

silyloxy-3-propyl-2-oxetanyl

245

OCH

2

CH

2

3-trimethyl-

silyloxy-3-butyl-2-oxetanyl

246

OCH

2

CH

2

3-oxetanyl

247

OCH

2

CH

2

2-furyl

248

OCH

2

CH

2

4,5-dihydro-2-furyl

249

OCH

2

CH

2

2,3-dihydro-2-furyl

250

OCH

2

CH

2

3-furyl

251

OCH

2

CH

2

4,5-dihydro-3-furyl

252

OCH

2

CH

2

2,3-dihydro-3-furyl

253

OCH

2

CH

2

2-thienyl

254

OCH

2

CH

2

4,5-dihydro-2-thienyl

255

OCH

2

CH

2

2,3-dihydro-2-thienyl

256

OCH

2

CH

2

5-chloro-2-thienyl

257

OCH

2

CH

2

5-methyl-2-thienyl

258

OCH

2

CH

2

3-thienyl

259

OCH

2

CH

2

4,5-dihydro-3-thienyl

260

OCH

2

CH

2

2,3-dihydro-3-thienyl

261

OCH

2

CH

2

2-pyrrolyl

262

OCH

2

CH

2

2,5-dihydro-2-pyrrolyl

263

OCH

2

CH

2

3-pyrrolyl

264

OCH

2

CH

2

2,5-dihydro-3-pyrrolyl

265

OCH

2

CH

2

3-isoxazolyl

266

OCH

2

CH

2

4-methyl-3-isoxazolyl

267

OCH

2

CH

2

5-methyl-3-isoxazolyl

268

OCH

2

CH

2

4,5-dimethyl-3-isoxazolyl

269

OCH

2

CH

2

4,5-dihydro-3-isoxazolyl

270

OCH

2

CH

2

4-methyl-4,5-dihydro-3-isoxazolyl

271

OCH

2

CH

2

5-methyl-4,5-dihydro-3-isoxazolyl

272

OCH

2

CH

2

4,5-dimethyl-4,5-dihydro-3-isoxazo-

lyl

273

OCH

2

CH

2

4-isoxazolyl

274

OCH

2

CH

2

3-methyl-4-isoxazolyl

275

OCH

2

CH

2

5-methyl-4-isoxazolyl

276

OCH

2

CH

2

5-cyclopropyl-4-isoxazolyl

277

OCH

2

CH

2

5-phenyl-4-isoxazolyl

278

OCH

2

CH

2

3,5-dimethyl-4-isoxazolyl

279

OCH

2

CH

2

4,5-dihydro-4-isoxazolyl

280

OCH

2

CH

2

3-methyl-4,5-dihydro-4-isoxazolyl

281

OCH

2

CH

2

5-methyl-4,5-dihydro-4-isoxazolyl

282

OCH

2

CH

2

3,5-dimethyl-4,5-dihydro-4-isoxazo-

lyl

283

OCH

2

CH

2

5-isoxazolyl

284

OCH

2

CH

2

3-methyl-5-isoxazolyl

285

OCH

2

CH

2

4-methyl-5-isoxazolyl

286

OCH

2

CH

2

3,4-dimethyl-5-isoxazolyl

287

OCH

2

CH

2

4,5-dihydro-5-isoxazolyl

288

OCH

2

CH

2

3-methyl-4,5-dihydro-5-isoxazolyl

289

OCH

2

CH

2

4-methyl-4,5-dihydro-5-isoxazolyl

290

OCH

2

CH

2

3,4-dimethyl-4,5-dihydro-5-isoxazo-

lyl

291

OCH

2

CH

2

3-isothiazolyl

292

OCH

2

CH

2

4-methyl-3-isothiazolyl

293

OCH

2

CH

2

5-methyl-3-isothiazolyl

294

OCH

2

CH

2

4-isothiazolyl

295

OCH

2

CH

2

3-methyl-4-isothiazolyl

296

OCH

2

CH

2

5-methyl-4-isothiazolyl

297

OCH

2

CH

2

5-isothiazolyl

298

OCH

2

CH

2

3-methyl-5-isothiazolyl

299

OCH

2

CH

2

4-methyl-5-isothiazolyl

300

OCH

2

CH

2

2-oxazolyl

301

OCH

2

CH

2

4-oxazolyl

302

OCH

2

CH

2

5-oxazolyl

303

OCH

2

CH

2

2-thiazolyl

304

OCH

2

CH

2

4-thiazolyl

305

OCH

2

CH

2

5-thiazolyl

306

OCH

2

CH

2

3-pyrazolyl

307

OCH

2

CH

2

4-pyrazolyl

308

OCH

2

CH

2

1-methyl-3-pyrazolyl

309

OCH

2

CH

2

1-methyl-4-pyrazolyl

310

OCH

2

CH

2

1-methyl-5-pyrazolyl

311

OCH

2

CH

2

2-imidazolyl

312

OCH

2

CH

2

1-methyl-2-imidazolyl

313

OCH

2

CH

2

5-methyl-[1,3,4]-2-oxadiazolyl

314

OCH

2

CH

2

5-methyl-[1,2,4]-3-oxadiazolyl

315

OCH

2

CH

2

5-methyl-[1,3,4]-2-thiadiazolyl

316

OCH

2

CH

2

5-methyl-[1,2,4]-3-thiadiazolyl

317

OCH

2

CH

2

[1,2,4]-3-triazolyl

318

OCH

2

CH

2

[1,2,3]-4-triazolyl

319

OCH

2

CH

2

2-pyridyl

320

OCH

2

CH

2

6-chloro-2-pyridyl

321

OCH

2

CH

2

6-methoxy-2-pyridyl

322

OCH

2

CH

2

6-trifluoromethyl-2-pyridyl

323

OCH

2

CH

2

3-pyridyl

324

OCH

2

CH

2

2-chloro-3-pyridyl

325

OCH

2

CH

2

2-methoxy-3-pyridyl

326

OCH

2

CH

2

4-pyridyl

327

OCH

2

CH

2

2-chloro-4-pyridyl

328

OCH

2

CH

2

2-methoxy-4-pyridyl

329

OCH

2

CH

2

2-ethoxy-4-pyridyl

330

OCH

2

CH

2

2-methylthio-4-pyridyl

331

OCH

2

CH

2

2-trifluoromethyl-5-pyridyl

332

OCH

2

CH

2

2-pyrimidinyl

333

OCH

2

CH

2

3-pyrimidinyl

334

OCH

2

CH

2

4-pyrimidinyl

335

OCH

2

CH

2

2-pyrazinyl

336

OCH

2

CH

2

3-pyridazinyl

337

OCH

2

CH

2

4-pyridazinyl

338

OCH

2

CH

2

2-(2H-1,3-oxazinyl)

339

OCH

2

CH

2

2-(6H-1,3-oxazinyl)

340

OCH

2

CH

2

4-(6H-1,3-oxazinyl)

341

OCH

2

CH

2

6-(6H-1,3-oxazinyl)

342

OCH

2

CH

2

[1,3,5]-2-triazinyl

343

OCH

2

CH

2

[1,2,4]-3-triazinyl

344

OCH

2

CH

2

[1,2,4]-5-triazinyl

345

OCH

2

CH

2

[1,2,4]-6-triazinyl

346

CH

2

CH

2

O

oxiranyl

347

CH

2

CH

2

O

3-methyl-2-oxiranyl

348

CH

2

CH

2

O

2-oxetanyl

349

CH

2

CH

2

O

3-hydroxy-3-methyl-2-oxetanyl

350

CH

2

CH

2

O

3-hydroxy-3-ethyl-2-oxetanyl

351

CH

2

CH

2

O

3-hydroxy-3-propyl-2-oxetanyl

352

CH

2

CH

2

O

3-hydroxy-3-butyl-2-oxetanyl

353

CH

2

CH

2

O

3-methoxy-3-methyl-2-oxetanyl

354

CH

2

CH

2

O

3-methoxy-3-ethyl-2-oxetanyl

355

CH

2

CH

2

O

3-methoxy-3-propyl-2-oxetanyl

356

CH

2

CH

2

O

3-methoxy-3-butyl-2-oxetanyl

357

CH

2

CH

2

O

3-trimethyl-

silyloxy-3-methyl-2-oxetanyl

358

CH

2

CH

2

O

3-trimethyl-

silyloxy-3-ethyl-2-oxetanyl

359

CH

2

CH

2

O

3-trimethyl-

silyloxy-3-propyl-2-oxetanyl

360

CH

2

CH

2

O

3-trimethyl-

silyloxy-3-butyl-2-oxetanyl

361

CH

2

CH

2

O

3-oxetanyl

362

CH

2

CH

2

O

2-furyl

363

CH

2

CH

2

O

4,5-dihydro-2-furyl

364

CH

2

CH

2

O

2,3-dihydro-2-furyl

365

CH

2

CH

2

O

3-furyl

366

CH

2

CH

2

O

4,5-dihydro-3-furyl

367

CH

2

CH

2

O

2,3-dihydro-3-furyl

368

CH

2

CH

2

O

2-thienyl

369

CH

2

CH

2

O

4,5-dihydro-2-thienyl

370

CH

2

CH

2

O

2,3-dihydro-2-thienyl

371

CH

2

CH

2

O

5-chloro-2-thienyl

372

CH

2

CH

2

O

5-methyl-2-thienyl

373

CH

2

CH

2

O

3-thienyl

374

CH

2

CH

2

O

4,5-dihydro-3-thienyl

375

CH

2

CH

2

O

2,3-dihydro-3-thienyl

376

CH

2

CH

2

O

2-pyrrolyl

377

CH

2

CH

2

O

2,5-dihydro-2-pyrrolyl

378

CH

2

CH

2

O

3-pyrrolyl

379

CH

2

CH

2

O

2,5-dihydro-3-pyrrolyl

380

CH

2

CH

2

O

3-isoxazolyl

381

CH

2

CH

2

O

4-methyl-3-isoxazolyl

382

CH

2

CH

2

O

5-methyl-3-isoxazolyl

383

CH

2

CH

2

O

4,5-dimethyl-3-isoxazolyl

384

CH

2

CH

2

O

4,5-dihydro-3-isoxazolyl

385

CH

2

CH

2

O

4-methyl-4,5-dihydro-3-isoxazolyl

386

CH

2

CH

2

O

5-methyl-4,5-dihydro-3-isoxazolyl

387

CH

2

CH

2

O

4,5-dimethyl-4,5-dihydro-3-isoxazo-

lyl

388

CH

2

CH

2

O

4-isoxazolyl

389

CH

2

CH

2

O

3-methyl-4-isoxazolyl

390

CH

2

CH

2

O

5-methyl-4-isoxazolyl

391

CH

2

CH

2

O

5-cyclopropyl-4-isoxazolyl

392

CH

2

CH

2

O

5-phenyl-4-isoxazolyl

393

CH

2

CH

2

O

3,5-dimethyl-4-isoxazolyl

394

CH

2

CH

2

O

4,5-dihydro-4-isoxazolyl

395

CH

2

CH

2

O

3-methyl-4,5-dihydro-4-isoxazolyl

396

CH

2

CH

2

O

5-methyl-4,5-dihydro-4-isoxazolyl

397

CH

2

CH

2

O

3,5-dimethyl-4,5-dihydro-4-isoxazo-

lyl

398

CH

2

CH

2

O

5-isoxazolyl

399

CH

2

CH

2

O

3-methyl-5-isoxazolyl

400

CH

2

CH

2

O

4-methyl-5-isoxazolyl

401

CH

2

CH

2

O

3,4-dimethyl-5-isoxazolyl

402

CH

2

CH

2

O

4,5-dihydro-5-isoxazolyl

403

CH

2

CH

2

O

3-methyl-4,5-dihydro-5-isoxazolyl

404

CH

2

CH

2

O

4-methyl-4,5-dihydro-5-isoxazolyl

405

CH

2

CH

2

O

3,4-dimethyl-4,5-dihydro-5-isoxazo-

lyl

406

CH

2

CH

2

O

3-isothiazolyl

407

CH

2

CH

2

O

4-methyl-3-isothiazolyl

408

CH

2

CH

2

O

5-methyl-3-isothiazolyl

409

CH

2

CH

2

O

4-isothiazolyl

410

CH

2

CH

2

O

3-methyl-4-isothiazolyl

411

CH

2

CH

2

O

5-methyl-4-isothiazolyl

412

CH

2

CH

2

O

5-isothiazolyl

413

CH

2

CH

2

O

3-methyl-5-isothiazolyl

414

CH

2

CH

2

O

4-methyl-5-isothiazolyl

415

CH

2

CH

2

O

2-oxazolyl

416

CH

2

CH

2

O

4-oxazolyl

417

CH

2

CH

2

O

5-oxazolyl

418

CH

2

CH

2

O

2-thiazolyl

419

CH

2

CH

2

O

4-thiazolyl

420

CH

2

CH

2

O

5-thiazolyl

421

CH

2

CH

2

O

3-pyrazolyl

422

CH

2

CH

2

O

4-pyrazolyl

423

CH

2

CH

2

O

1-methyl-3-pyrazolyl

424

CH

2

CH

2

O

1-methyl-4-pyrazolyl

425

CH

2

CH

2

O

1-methyl-5-pyrazolyl

426

CH

2

CH

2

O

2-imidazolyl

427

CH

2

CH

2

O

1-methyl-2-imidazolyl

428

CH

2

CH

2

O

5-methyl-[1,3,4]-2-oxadiazolyl

429

CH

2

CH

2

O

5-methyl-[1,2,4]-3-oxadiazolyl

430

CH

2

CH

2

O

5-methyl-[1,3,4]-2-thiadiazolyl

431

CH

2

CH

2

O

5-methyl-[1,2,4]-3-thiadiazolyl

432

CH

2

CH

2

O

[1,2,4]-3-triazolyl

433

CH

2

CH

2

O

[1,2,3]-4-triazolyl

434

CH

2

CH

2

O

2-pyridyl

435

CH

2

CH

2

O

6-chloro-2-pyridyl

436

CH

2

CH

2

O

6-methoxy-2-pyridyl

437

CH

2

CH

2

O

6-trifiuoromethyl-2-pyridyl

438

CH

2

CH

2

O

3-pyridyl

439

CH

2

CH

2

O

2-chloro-3-pyridyl

440

CH

2

CH

2

O

2-methoxy-3-pyridyl

441

CH

2

CH

2

O

4-pyridyl

442

CH

2

CH

2

O

2-chloro-4-pyridyl

443

CH

2

CH

2

O

2-methoxy-4-pyridyl

444

CH

2

CH

2

O

2-ethoxy-4-pyridyl

445

CH

2

CH

2

O

2-methylthio-4-pyridyl

446

CH

2

CH

2

O

2-trifiuoromethyl-5-pyridyl

447

CH

2

CH

2

O

2-pyrimidinyl

448

CH

2

CH

2

O

3-pyrimidinyl

449

CH

2

CH

2

O

4-pyrimidinyl

450

CH

2

CH

2

O

2-pyrazinyl

451

CH

2

CH

2

O

3-pyridazinyl

452

CH

2

CH

2

O

4-pyridazinyl

453

CH

2

CH

2

O

2-(2H-1,3-oxazinyl)

454

CH

2

CH

2

O

2-(6H-1,3-oxazinyl)

455

CH

2

CH

2

O

4-(6H-1,3-oxazinyl)

456

CH

2

CH

2

O

6-(6H-1,3-oxazinyl)

457

CH

2

CH

2

O

[1,3,5]-2-triazinyl

458

CH

2

CH

2

O

[1,2,4]-3-triazinyl

459

CH

2

CH

2

O

[1,2,4]-5-triazinyl

460

CH

2

CH

2

O

[1,2,4]-6-triazinyl

461

CH

2

OCH

2

oxiranyl

462

CH

2

OCH

2

3-methyl-2-oxiranyl

463

CH

2

OCH

2

2-oxetanyl

464

CH

2

OCH

2

3-hydroxy-3-methyl-2-oxetanyl

465

CH

2

OCH

2

3-hydroxy-3-ethyl-2-oxetanyl

466

CH

2

OCH

2

3-hydroxy-3-propyl-2-oxetanyl

467

CH

2

OCH

2

3-hydroxy-3-butyl-2-oxetanyl

468

CH

2

OCH

2

3-methoxy-3-methyl-2-oxetanyl

469

CH

2

OCH

2

3-methoxy-3-ethyl-2-oxetanyl

470

CH

2

OCH

2

3-methoxy-3-propyl-2-oxetanyl

471

CH

2

OCH

2

3-methoxy-3-butyl-2-oxetanyl

472

CH

2

OCH

2

3-trimethyl-

silyloxy-3-methyl-2-oxetanyl

473

CH

2

OCH

2

3-trimethyl-

silyloxy-3-ethyl-2-oxetanyl

474

CH

2

OCH

2

3-trimethyl-

silyloxy-3-propyl-2-oxetanyl

475

CH

2

OCH

2

3-trimethyl-

silyloxy-3-butyl-2-oxetanyl

476

CH

2

OCH

2

3-oxetanyl

477

CH

2

OCH

2

2-furyl

478

CH

2

OCH

2

4,5-dihydro-2-furyl

479

CH

2

OCH

2

2,3-dihydro-2-furyl

480

CH

2

OCH

2

3-furyl

481

CH

2

OCH

2

4,5-dihydro-3-furyl

482

CH

2

OCH

2

2,3-dihydro-3-furyl

483

CH

2

OCH

2

2-thienyl

484

CH

2

OCH

2

4,5-dihydro-2-thienyl

485

CH

2

OCH

2

2,3-dihydro-2-thienyl

486

CH

2

OCH

2

5-chloro-2-thienyl

487

CH

2

OCH

2

5-methyl-2-thienyl

488

CH

2

OCH

2

3-thienyl

489

CH

2

OCH

2

4,5-dihydro-3-thienyl

490

CH

2

OCH

2

2,3-dihydro-3-thienyl

491

CH

2

OCH

2

2-pyrrolyl

492

CH

2

OCH

2

2,5-dihydro-2-pyrrolyl

493

CH

2

OCH

2

3-pyrrolyl

494

CH

2

OCH

2

2,5-dihydro-3-pyrrolyl

495

CH

2

OCH

2

3-isoxazolyl

496

CH

2

OCH

2

4-methyl-3-isoxazolyl

497

CH

2

OCH

2

5-methyl-3-isoxazolyl

498

CH

2

OCH

2

4,5-dimethyl-3-isoxazolyl

499

CH

2

OCH

2

4,5-dihydro-3-isoxazolyl

500

CH

2

OCH

2

4-methyl-4,5-dihydro-3-isoxazolyl

501

CH

2

OCH

2

5-methyl-4,5-dihydro-3-isoxazolyl

502

CH

2

OCH

2

4,5-dimethyl-4,5-dihydro-3-isoxazo-

lyl

503

CH

2

OCH

2

4-isoxazolyl

504

CH

2

OCH

2

3-methyl-4-isoxazolyl

505

CH

2

OCH

2

5-methyl-4-isoxazolyl

506

CH

2

OCH

2

5-cyclopropyl-4-isoxazolyl

507

CH

2

OCH

2

5-phenyl-4-isoxazolyl

508

CH

2

OCH

2

3,5-dimethyl-4-isoxazolyl

509

CH

2

OCH

2

4,5-dihydro-4-isoxazolyl

510

CH

2

OCH

2

3-methyl-4,5-dihydro-4-isoxazolyl

511

CH

2

OCH

2

5-methyl-4,5-dihydro-4-isoxazolyl

512

CH

2

OCH

2

3,5-dimethyl-4,5-dihydro-4-isoxazo-

lyl

513

CH

2

OCH

2

5-isoxazolyl

514

CH

2

OCH

2

3-methyl-5-isoxazolyl

515

CH

2

OCH

2

4-methyl-5-isoxazolyl

516

CH

2

OCH

2

3,4-dimethyl-5-isoxazolyl

517

CH

2

OCH

2

4,5-dihydro-5-isoxazolyl

518

CH

2

OCH

2

3-methyl-4,5-dihydro-5-isoxazolyl

519

CH

2

OCH

2

4-methyl-4,5-dihydro-5-isoxazolyl

520

CH

2

OCH

2

3,4-dimethyl-4,5-dihydro-5-isoxazo-

lyl

521

CH

2

OCH

2

3-isothiazolyl

522

CH

2

OCH

2

4-methyl-3-isothiazolyl

523

CH

2

OCH

2

5-methyl-3-isothiazolyl

524

CH

2

OCH

2

4-isothiazolyl

525

CH

2

OCH

2

3-methyl-4-isothiazolyl

526

CH

2

OCH

2

5-methyl-4-isothiazolyl

527

CH

2

OCH

2

5-isothiazolyl

528

CH

2

OCH

2

3-methyl-5-isothiazolyl

529

CH

2

OCH

2

4-methyl-5-isothiazolyl

530

CH

2

OCH

2

2-oxazolyl

531

CH

2

OCH

2

4-oxazolyl

532

CH

2

OCH

2

5-oxazolyl

533

CH

2

OCH

2

2-thiazolyl

534

CH

2

OCH

2

4-thiazolyl

535

CH

2

OCH

2

5-thiazolyl

536

CH

2

OCH

2

3-pyrazolyl

537

CH

2

OCH

2

4-pyrazolyl

538

CH

2

OCH

2

1-methyl-3-pyrazolyl

539

CH

2

OCH

2

1-methyl-4-pyrazolyl

540

CH

2

OCH

2

1-methyl-5-pyrazolyl

541

CH

2

OCH

2

2-imidazolyl

542

CH

2

OCH

2

1-methyl-2-imidazolyl

543

CH

2

OCH

2

5-methyl-[1,3,4]-2-oxadiazolyl

544

CH

2

OCH

2

5-methyl-[1,2,4]-3-oxadiazolyl

545

CH

2

OCH

2

5-methyl-[1,3,4]-2-thiadiazolyl

546

CH

2

OCH

2

5-methyl-[1,2,4]-3-thiadiazolyl

547

CH

2

OCH

2

[1,2,4]-3-triazolyl

548

CH

2

OCH

2

[1,2,3]-4-triazolyl

549

CH

2

OCH

2

2-pyridyl

550

CH

2

OCH

2

6-chloro-2-pyridyl

551

CH

2

OCH

2

6-methoxy-2-pyridyl

552

CH

2

OCH

2

6-trifluoromethyl-2-pyridyl

553

CH

2

OCH

2

3-pyridyl

554

CH

2

OCH

2

2-chloro-3-pyridyl

555

CH

2

OCH

2

2-methoxy-3-pyridyl

556

CH

2

OCH

2

4-pyridyl

557

CH

2

OCH

2

2-chloro-4-pyridyl

558

CH

2

OCH

2

2-methoxy-4-pyridyl

559

CH

2

OCH

2

2-ethoxy-4-pyridyl

560

CH

2

OCH

2

2-methylthio-4-pyridyl

561

CH

2

OCH

2

2-trifluoromethyl-5-pyridyl

562

CH

2

OCH

2

2-pyrimidinyl

563

CH

2

OCH

2

3-pyrimidinyl

564

CH

2

OCH

2

4-pyrimidinyl

565

CH

2

OCH

2

2-pyrazinyl

566

CH

2

OCH

2

3-pyridazinyl

567

CH

2

OCH

2

4-pyridazinyl

568

CH

2

OCH

2

2-(2H-1,3-oxazinyl)

569

CH

2

OCH

2

2-(6H-1,3-oxazinyl)

570

CH

2

OCH

2

4-(6H-1,3-oxazinyl)

571

CH

2

OCH

2

6-(6H-1,3-oxazinyl)

572

CH

2

OCH

2

[1,3,5]-2-triazinyl

573

CH

2

OCH

2

[1,2,4]-3-triazinyl

574

CH

2

OCH

2

[1,2,4]-5-triazinyl

575

CH

2

OCH

2

[1,2,4]-6-triazinyl

576

CH

2

OCH

2

CH═CH

oxiranyl

577

CH

2

OCH

2

CH═CH

3-methyl-2-oxiranyl

578

CH

2

OCH

2

CH═CH

2-oxetanyl

579

CH

2

OCH

2

CH═CH

3-hydroxy-3-methyl-2-oxetanyl

580

CH

2

OCH

2

CH═CH

3-hydroxy-3-ethyl-2-oxetanyl

581

CH

2

OCH

2

CH═CH

3-hydroxy-3-propyl-2-oxetanyl

582

CH

2

OCH

2

CH═CH

3-hydroxy-3-butyl-2-oxetanyl

583

CH

2

OCH

2

CH═CH

3-methoxy-3-methyl-2-oxetanyl

584

CH

2

OCH

2

CH═CH

3-methoxy-3-ethyl-2-oxetanyl

585

CH

2

OCH

2

CH═CH

3-methoxy-3-propyl-2-oxetanyl

586

CH

2

OCH

2

CH═CH

3-methoxy-3-butyl-2-oxetanyl

587

CH

2

OCH

2

CH═CH

3-trimethyl-

silyloxy-3-methyl-2-oxetanyl

588

CH

2

OCH

2

CH═CH

3-trimethyl-

silyloxy-3-ethyl-2-oxetanyl

589

CH

2

OCH

2

CH═CH

3-trimethyl-

silyloxy-3-propyl-2-oxetanyl

590

CH

2

OCH

2

CH═CH

3-trimethyl-

silyloxy-3-butyl-2-oxetanyl

591

CH

2

OCH

2

CH═CH

3-oxetanyl

592

CH

2

OCH

2

CH═CH

2-furyl

593

CH

2

OCH

2

CH═CH

4,5-dihydro-2-furyl

594

CH

2

OCH

2

CH═CH

2,3-dihydro-2-furyl

595

CH

2

OCH

2

CH═CH

3-furyl

596

CH

2

OCH

2

CH═CH

4,5-dihydro-3-furyl

597

CH

2

OCH

2

CH═CH

2,3-dihydro-3-furyl

598

CH

2

OCH

2

CH═CH

2-thienyl

599

CH

2

OCH

2

CH═CH

4,5-dihydro-2-thienyl

600

CH

2

OCH

2

CH═CH

2,3-dihydro-2-thienyl

601

CH

2

OCH

2

CH═CH

5-chloro-2-thienyl

602

CH

2

OCH

2

CH═CH

5-methyl-2-thienyl

603

CH

2

OCH

2

CH═CH

3-thienyl

604

CH

2

OCH

2

CH═CH

4,5-dihydro-3-thienyl

605

CH

2

OCH

2

CH═CH

2,3-dihydro-3-thienyl

606

CH

2

OCH

2

CH═CH

2-pyrrolyl

607

CH

2

OCH

2

CH═CH

2,5-dihydro-2-pyrrolyl

608

CH

2

OCH

2

CH═CH

3-pyrrolyl

609

CH

2

OCH

2

CH═CH

2,5-dihydro-3-pyrrolyl

610

CH

2

OCH

2

CH═CH

3-isoxazolyl

611

CH

2

OCH

2

CH═CH

4-methyl-3-isoxazolyl

612

CH

2

OCH

2

CH═CH

5-methyl-3-isoxazolyl

613

CH

2

OCH

2

CH═CH

4,5-dimethyl-3-isoxazolyl

614

CH

2

OCH

2

CH═CH

4,5-dihydro-3-isoxazolyl

615

CH

2

OCH

2

CH═CH

4-methyl-4,5-dihydro-3-isoxazolyl

616

CH

2

OCH

2

CH═CH

5-methyl-4,5-dihydro-3-isoxazolyl

617

CH

2

OCH

2

CH═CH

4,5-dimethyl-4,5-dihydro-3-isoxazo-

lyl

618

CH

2

OCH

2

CH═CH

4-isoxazolyl

619

CH

2

OCH

2

CH═CH

3-methyl-4-isoxazolyl

620

CH

2

OCH

2

CH═CH

5-methyl-4-isoxazolyl

621

CH

2

OCH

2

CH═CH

5-cyclopropyl-4-isoxazolyl

622

CH

2

OCH

2

CH═CH

5-phenyl-4-isoxazolyl

623

CH

2

OCH

2

CH═CH

3,5-dimethyl-4-isoxazolyl

624

CH

2

OCH

2

CH═CH

4,5-dihydro-4-isoxazolyl

625

CH

2

OCH

2

CH═CH

3-methyl-4,5-dihydro-4-isoxazolyl

626

CH

2

OCH

2

CH═CH

5-methyl-4,5-dihydro-4-isoxazolyl

627

CH

2

OCH

2

CH═CH

3,5-dimethyl-4,5-dihydro-4-isoxazo-

lyl

628

CH

2

OCH

2

CH═CH

5-isoxazolyl

629

CH

2

OCH

2

CH═CH

3-methyl-5-isoxazolyl

630

CH

2

OCH

2

CH═CH

4-methyl-5-isoxazolyl

631

CH

2

OCH

2

CH═CH

3,4-dimethyl-5-isoxazolyl

632

CH

2

OCH

2

CH═CH

4,5-dihydro-5-isoxazolyl

633

CH

2

OCH

2

CH═CH

3-methyl-4,5-dihydro-5-isoxazolyl

634

CH

2

OCH

2

CH═CH

4-methyl-4,5-dihydro-5-isoxazolyl

635

CH

2

OCH

2

CH═CH

3,4-dimethyl-4,5-dihydro-5-isoxazo-

lyl

636

CH

2

OCH

2

CH═CH

3-isothiazolyl

637

CH

2

OCH

2

CH═CH

4-methyl-3-isothiazolyl

638

CH

2

OCH

2

CH═CH

5-methyl-3-isothiazolyl

639

CH

2

OCH

2

CH═CH

4-isothiazolyl

640

CH

2

OCH

2

CH═CH

3-methyl-4-isothiazolyl

641

CH

2

OCH

2

CH═CH

5-methyl-4-isothiazolyl

642

CH

2

OCH

2

CH═CH

5-isothiazolyl

643

CH

2

OCH

2

CH═CH

3-methyl-5-isothiazolyl

644

CH

2

OCH

2

CH═CH

4-methyl-5-isothiazolyl

645

CH

2

OCH

2

CH═CH

2-oxazolyl

646

CH

2

OCH

2

CH═CH

4-oxazolyl

647

CH

2

OCH

2

CH═CH

5-oxazolyl

648

CH

2

OCH

2

CH═CH

2-thiazolyl

649

CH

2

OCH

2

CH═CH

4-thiazolyl

650

CH

2

OCH

2

CH═CH

5-thiazolyl

651

CH

2

OCH

2

CH═CH

3-pyrazolyl

652

CH

2

OCH

2

CH═CH

4-pyrazolyl

653

CH

2

OCH

2

CH═CH

1-methyl-3-pyrazolyl

654

CH

2

OCH

2

CH═CH

1-methyl-4-pyrazolyl

655

CH

2

OCH

2

CH═CH

1-methyl-5-pyrazolyl

656

CH

2

OCH

2

CH═CH

2-imidazolyl

657

CH

2

OCH

2

CH═CH

1-methyl-2-imidazolyl

658

CH

2

OCH

2

CH═CH

5-methyl-[1,3,4]-2-oxadiazolyl

659

CH

2

OCH

2

CH═CH

5-methyl-[1,2,4]-3-oxadiazolyl

660

CH

2

OCH

2

CH═CH

5-methyl-[1,3,4]-2-thiadiazolyl

661

CH

2

OCH

2

CH═CH

5-methyl-[1,2,4]-3-thiadiazolyl

662

CH

2

OCH

2

CH═CH

[1,2,4]-3-triazolyl

663

CH

2

OCH

2

CH═CH

[1,2,3]-4-triazolyl

664

CH

2

OCH

2

CH═CH

2-pyridyl

665

CH

2

OCH

2

CH═CH

6-chloro-2-pyridyl

666

CH

2

OCH

2

CH═CH

6-methoxy-2-pyridyl

667

CH

2

OCH

2

CH═CH

6-trifluoromethyl-2-pyridyl

668

CH

2

OCH

2

CH═CH

3-pyridyl

669

CH

2

OCH

2

CH═CH

2-chloro-3-pyridyl

670

CH

2

OCH

2

CH═CH

2-methoxy-3-pyridyl

671

CH

2

OCH

2

CH═CH

4-pyridyl

672

CH

2

OCH

2

CH═CH

2-chloro-4-pyridyl

673

CH

2

OCH

2

CH═CH

2-methoxy-4-pyridyl

674

CH

2

OCH

2

CH═CH

2-ethoxy-4-pyridyl

675

CH

2

OCH

2

CH═CH

2-methylthio-4-pyridyl

676

CH

2

OCH

2

CH═CH

2-trifluoromethyl-5-pyridyl

677

CH

2

OCH

2

CH═CH

2-pyrimidinyl

678

CH

2

OCH

2

CH═CH

3-pyrimidinyl

679

CH

2

OCH

2

CH═CH

4-pyrimidinyl

680

CH

2

OCH

2

CH═CH

2-pyrazinyl

681

CH

2

OCH

2

CH═CH

3-pyridazinyl

682

CH

2

OCH

2

CH═CH

4-pyridazinyl

683

CH

2

OCH

2

CH═CH

2-(2H-1,3-oxazinyl)

684

CH

2

OCH

2

CH═CH

2-(6H-1,3-oxazinyl)

685

CH

2

OCH

2

CH═CH

4-(6H-1,3-oxazinyl)

686

CH

2

OCH

2

CH═CH

6-(6H-1,3-oxazinyl)

687

CH

2

OCH

2

CH═CH

[1,3,5]-2-triazinyl

688

CH

2

OCH

2

CH═CH

[1,2,4]-3-triazinyl

689

CH

2

OCH

2

CH═CH

[1,2,4]-5-triazinyl

690

CH

2

OCH

2

CH═CH

[1,2,4]-6-triazinyl

691

CH═CHCH

2

O

oxiranyl

692

CH═CHCH

2

O

3-methyl-2-oxiranyl

693

CH═CHCH

2

O

2-oxetanyl

694

CH═CHCH

2

O

3-hydroxy-3-methyl-2-oxetanyl

695

CH═CHCH

2

O

3-hydroxy-3-ethyl-2-oxetanyl

696

CH═CHCH

2

O

3-hydroxy-3-propyl-2-oxetanyl

697

CH═CHCH

2

O

3-hydroxy-3-butyl-2-oxetanyl

698

CH═CHCH

2

O

3-methoxy-3-methyl-2-oxetanyl

699

CH═CHCH

2

O

3-methoxy-3-ethyl-2-oxetanyl

700

CH═CHCH

2

O

3-methoxy-3-propyl-2-oxetanyl

701

CH═CHCH

2

O

3-methoxy-3-butyl-2-oxetanyl

702

CH═CHCH

2

O

3-trimethyl-

silyloxy-3-methyl-2-oxetanyl

703

CH═CHCH

2

O

3-trimethyl-

silyloxy-3-ethyl-2-oxetanyl

704

CH═CHCH

2

O

3-trimethyl-

silyloxy-3-propyl-2-oxetanyl

705

CH═CHCH

2

O

3-trimethyl-

silyloxy-3-butyl-2-oxetanyl

706

CH═CHCH

2

O

3-oxetanyl

707

CH═CHCH

2

O

2-furyl

708

CH═CHCH

2

O

4,5-dihydro-2-furyl

709

CH═CHCH

2

O

2,3-dihydro-2-furyl

710

CH═CHCH

2

O

3-furyl

711

CH═CHCH

2

O

4,5-dihydro-3-furyl

712

CH═CHCH

2

O

2,3-dihydro-3-furyl

713

CH═CHCH

2

O

2-thienyl

714

CH═CHCH

2

O

4,5-dihydro-2-thienyl

715

CH═CHCH

2

O

2,3-dihydro-2-thienyl

716

CH═CHCH

2

O

5-chloro-2-thienyl

717

CH═CHCH

2

O

5-methyl-2-thienyl

718

CH═CHCH

2

O

3-thienyl

719

CH═CHCH

2

O

4,5-dihydro-3-thienyl

720

CH═CHCH

2

O

2,3-dihydro-3-thienyl

721

CH═CHCH

2

O

2-pyrrolyl

722

CH═CHCH

2

O

2,5-dihydro-2-pyrrolyl

723

CH═CHCH

2

O

3-pyrrolyl

724

CH═CHCH

2

O

2,5-dihydro-3-pyrrolyl

725

CH═CHCH

2

O

3-isoxazolyl

726

CH═CHCH

2

O

4-methyl-3-isoxazolyl

727

CH═CHCH

2

O

5-methyl-3-isoxazolyl

728

CH═CHCH

2

O

4,5-dimethyl-3-isoxazolyl

729

CH═CHCH

2

O

4,5-dihydro-3-isoxazolyl

730

CH═CHCH

2

O

4-methyl-4,5-dihydro-3-isoxazolyl

731

CH═CHCH

2

O

5-methyl-4,5-dihydro-3-isoxazolyl

732

CH═CHCH

2

O

4,5-dimethyl-4,5-dihydro-3-isoxazo-

lyl

733

CH═CHCH

2

O

4-isoxazolyl

734

CH═CHCH

2

O

3-methyl-4-isoxazolyl

735

CH═CHCH

2

O

5-methyl-4-isoxazolyl

736

CH═CHCH

2

O

5-cyclopropyl-4-isoxazolyl

737

CH═CHCH

2

O

5-phenyl-4-isoxazolyl

738

CH═CHCH

2

O

3,5-dimethyl-4-isoxazolyl

739

CH═CHCH

2

O

4,5-dihydro-4-isoxazolyl

740

CH═CHCH

2

O

3-methyl-4,5-dihydro-4-isoxazolyl

741

CH═CHCH

2

O

5-methyl-4,5-dihydro-4-isoxazolyl

742

CH═CHCH

2

O

3,5-dimethyl-4,5-dihydro-4-isoxazo-

lyl

743

CH═CHCH

2

O

5-isoxazolyl

744

CH═CHCH

2

O

3-methyl-5-isoxazolyl

745

CH═CHCH

2

O

4-methyl-5-isoxazolyl

746

CH═CHCH

2

O

3,4-dimethyl-5-isoxazolyl

747

CH═CHCH

2

O

4,5-dihydro-5-isoxazolyl

748

CH═CHCH

2

O

3-methyl-4,5-dihydro-5-isoxazolyl

749

CH═CHCH

2

O

4-methyl-4,5-dihydro-5-isoxazolyl

750

CH═CHCH

2

O

3,4-dimethyl-4,5-dihydro-5-isoxazo-

lyl

751

CH═CHCH

2

O

3-isothiazolyl

752

CH═CHCH

2

O

4-methyl-3-isothiazolyl

753

CH═CHCH

2

O

5-methyl-3-isothiazolyl

754

CH═CHCH

2

O

4-isothiazolyl

755

CH═CHCH

2

O

3-methyl-4-isothiazolyl

756

CH═CHCH

2

O

5-methyl-4-isothiazolyl

757

CH═CHCH

2

O

5-isothiazolyl

758

CH═CHCH

2

O

3-methyl-5-isothiazolyl

759

CH═CHCH

2

O

4-methyl-5-isothiazolyl

760

CH═CHCH

2

O

2-oxazolyl

761

CH═CHCH

2

O

4-oxazolyl

762

CH═CHCH

2

O

5-oxazolyl

763

CH═CHCH

2

O

2-thiazolyl

764

CH═CHCH

2

O

4-thiazolyl

765

CH═CHCH

2

O

5-thiazolyl

766

CH═CHCH

2

O

3-pyrazolyl

767

CH═CHCH

2

O

4-pyrazolyl

768

CH═CHCH

2

O

1-methyl-3-pyrazolyl

769

CH═CHCH

2

O

1-methyl-4-pyrazolyl

770

CH═CHCH

2

O

1-methyl-5-pyrazolyl

771

CH═CHCH

2

O

2-imidazolyl

772

CH═CHCH

2

O

1-methyl-2-imidazolyl

773

CH═CHCH

2

O

5-methyl-[1,3,4]-2-oxadiazolyl

774

CH═CHCH

2

O

5-methyl-[1,2,4]-3-oxadiazolyl

775

CH═CHCH

2

O

5-methyl-[1,3,4]-2-thiadiazolyl

776

CH═CHCH

2

O

5-methyl-[1,2,4]-3-thiadiazolyl

777

CH═CHCH

2

O

[1,2,4]-3-triazolyl

778

CH═CHCH

2

O

[1,2,3]-4-triazolyl

779

CH═CHCH

2

O

2-pyridyl

780

CH═CHCH

2

O

6-chloro-2-pyridyl

781

CH═CHCH

2

O

6-methoxy-2-pyridyl

782

CH═CHCH

2

O

6-trifluoromethyl-2-pyridyl

783

CH═CHCH

2

O

3-pyridyl

784

CH═CHCH

2

O

2-chloro-3-pyridyl

785

CH═CHCH

2

O

2-methoxy-3-pyridyl

786

CH═CHCH

2

O

4-pyridyl

787

CH═CHCH

2

O

2-chloro-4-pyridyl

788

CH═CHCH

2

O

2-methoxy-4-pyridyl

789

CH═CHCH

2

O

2-ethoxy-4-pyridyl

790

CH═CHCH

2

O

2-methylthio-4-pyridyl

791

CH═CHCH

2

O

2-trifluoromethyl-5-pyridyl

792

CH═CHCH

2

O

2-pyrimidinyl

793

CH═CHCH

2

O

3-pyrimidinyl

794

CH═CHCH

2

O

4-pyrimidinyl

795

CH═CHCH

2

O

2-pyrazinyl

796

CH═CHCH

2

O

3-pyridazinyl

797

CH═CHCH

2

O

4-pyridazinyl

798

CH═CHCH

2

O

2-(2H-1,3-oxazinyl)

799

CH═CHCH

2

O

2-(6H-1,3-oxazinyl)

800

CH═CHCH

2

O

4-(6H-1,3-oxazinyl)

801

CH═CHCH

2

O

6-(6H-1,3-oxazinyl)

802

CH═CHCH

2

O

[1,3,5]-2-triazinyl

803

CH═CHCH

2

O

[1,2,4]-3-triazinyl

804

CH═CHCH

2

O

[1,2,4]-5-triazinyl

805

CH═CHCH

2

O

[1,2,4]-6-triazinyl

806

—C≡C—CH

2

O

oxiranyl

807

—C≡C—CH

2

O

3-methyl-2-oxiranyl

808

—C≡C—CH

2

O

2-oxetanyl

809

—C≡C—CH

2

O

3-hydroxy-3-methyl-2-oxetanyl

810

—C≡C—CH

2

O

3-hydroxy-3-ethyl-2-oxetanyl

811

—C≡C—CH

2

O

3-hydroxy-3-propyl-2-oxetanyl

812

—C≡C—CH

2

O

3-hydroxy-3-butyl-2-oxetanyl

813

—C≡C—CH

2

O

3-methoxy-3-methyl-2-oxetanyl

814

—C≡C—CH

2

O

3-methoxy-3-ethyl-2-oxetanyl

815

—C≡C—CH

2

O

3-methoxy-3-propyl-2-oxetanyl

816

—C≡C—CH

2

O

3-methoxy-3-butyl-2-oxetanyl

817

—C≡C—CH

2

O

3-trimethyl-

silyloxy-3-methyl-2-oxetanyl

818

—C≡C—CH

2

O

3-trimethyl-

silyloxy-3-ethyl-2-oxetanyl

819

—C≡C—CH

2

O

3-trimethyl-

silyloxy-3-propyl-2-oxetanyl

820

—C≡C—CH

2

O

3-trimethyl-

silyloxy-3-butyl-2-oxetanyl

821

—C≡C—CH

2

O

3-oxetanyl

822

—C≡C—CH

2

O

2-furyl

823

—C≡C—CH

2

O

4,5-dihydro-2-furyl

824

—C≡C—CH

2

O

2,3-dihydro-2-furyl

825

—C≡C—CH

2

O

3-furyl

826

—C≡C—CH

2

O

4,5-dihydro-3-furyl

827

—C≡C—CH

2

O

2,3-dihydro-3-furyl

828

—C≡C—CH

2

O

2-thienyl

829

—C≡C—CH

2

O

4,5-dihydro-2-thienyl

830

—C≡C—CH

2

O

2,3-dihydro-2-thienyl

831

—C≡C—CH

2

O

5-chloro-2-thienyl

832

—C≡C—CH

2

O

5-methyl-2-thienyl

833

—C≡C—CH

2

O

3-thienyl

834

—C≡C—CH

2

O

4,5-dihydro-3-thienyl

835

—C≡C—CH

2

O

2,3-dihydro-3-thienyl

836

—C≡C—CH

2

O

2-pyrrolyl

837

—C≡C—CH

2

O

2,5-dihydro-2-pyrrolyl

838

—C≡C—CH

2

O

3-pyrrolyl

839

—C≡C—CH

2

O

2,5-dihydro-3-pyrrolyl

840

—C≡C—CH

2

O

3-isoxazolyl

841

—C≡C—CH

2

O

4-methyl-3-isoxazolyl

842

—C≡C—CH

2

O

5-methyl-3-isoxazolyl

843

—C≡C—CH

2

O

4,5-dimethyl-3-isoxazolyl

844

—C≡C—CH

2

O

4,5-dihydro-3-isoxazolyl

845

—C≡C—CH

2

O

4-methyl-4,5-dihydro-3-isoxazolyl

846

—C≡C—CH

2

O

5-methyl-4,5-dihydro-3-isoxazolyl

847

—C≡C—CH

2

O

4,5-dimethyl-4,5-dihydro-3-isoxazo-

lyl

848

—C≡C—CH

2

O

4-isoxazolyl

849

—C≡C—CH

2

O

3-methyl-4-isoxazolyl

850

—C≡C—CH

2

O

5-methyl-4-isoxazolyl

851

—C≡C—CH

2

O

5-cyclopropyl-4-isoxazolyl

852

—C≡C—CH

2

O

5-phenyl-4-isoxazolyl

853

—C≡C—CH

2

O

3,5-dimethyl-4-isoxazolyl

854

—C≡C—CH

2

O

4,5-dihydro-4-isoxazolyl

855

—C≡C—CH

2

O

3-methyl-4,5-dihydro-4-isoxazolyl

856

—C≡C—CH

2

O

5-methyl-4,5-dihydro-4-isoxazolyl

857

—C≡C—CH

2

O

3,5-dimethyl-4,5-dihydro-4-isoxazo-

lyl

858

—C≡C—CH

2

O

5-isoxazolyl

859

—C≡C—CH

2

O

3-methyl-5-isoxazolyl

860

—C≡C—CH

2

O

4-methyl-5-isoxazolyl

861

—C≡C—CH

2

O

3,4-dimethyl-5-isoxazolyl

862

—C≡C—CH

2

O

4,5-dihydro-5-isoxazolyl

863

—C≡C—CH

2

O

3-methyl-4,5-dihydro-5-isoxazolyl

864

—C≡C—CH

2

O

4-methyl-4,5-dihydro-5-isoxazolyl

865

—C≡C—CH

2

O

3,4-dimethyl-4,5-dihydro-5-isoxazo-

lyl

866

—C≡C—CH

2

O

3-isothiazolyl

867

—C≡C—CH

2

O

4-methyl-3-isothiazolyl

868

—C≡C—CH

2

O

5-methyl-3-isothiazolyl

869

—C≡C—CH

2

O

4-isothiazolyl

870

—C≡C—CH

2

O

3-methyl-4-isothiazolyl

871

—C≡C—CH

2

O

5-methyl-4-isothiazolyl

872

—C≡C—CH

2

O

5-isothiazolyl

873

—C≡C—CH

2

O

3-methyl-5-isothiazolyl

874

—C≡C—CH

2

O

4-methyl-5-isothiazolyl

875

—C≡C—CH

2

O

2-oxazolyl

876

—C≡C—CH

2

O

4-oxazolyl

877

—C≡C—CH

2

O

5-oxazolyl

878

—C≡C—CH

2

O

2-thiazolyl

879

—C≡C—CH

2

O

4-thiazolyl

880

—C≡C—CH

2

O

5-thiazolyl

881

—C≡C—CH

2

O

3-pyrazolyl

882

—C≡C—CH

2

O

4-pyrazolyl

883

—C≡C—CH

2

O

1-methyl-3-pyrazolyl

884

—C≡C—CH

2

O

1-methyl-4-pyrazolyl

885

—C≡C—CH

2

O

1-methyl-5-pyrazolyl

886

—C≡C—CH

2

O

2-imidazolyl

887

—C≡C—CH

2

O

1-methyl-2-imidazolyl

888

—C≡C—CH

2

O

5-methyl-[1,3,4]-2-oxadiazolyl

889

—C≡C—CH

2

O

5-methyl-[1,2,4]-3-oxadiazolyl

890

—C≡C—CH

2

O

5-methyl-[1,3,4]-2-thiadiazolyl

891

—C≡C—CH

2

O

5-methyl-[1,2,4]-3-thiadiazolyl

892

—C≡C—CH

2

O

[1,2,4]-3-triazolyl

893

—C≡C—CH

2

O

[1,2,3]-4-triazolyl

894

—C≡C—CH

2

O

2-pyridyl

895

—C≡C—CH

2

O

6-chloro-2-pyridyl

896

—C≡C—CH

2

O

6-methoxy-2-pyridyl

897

—C≡C—CH

2

O

6-trifluoromethyl-2-pyridyl

898

—C≡C—CH

2

O

3-pyridyl

899

—C≡C—CH

2

O

2-chloro-3-pyridyl

900

—C≡C—CH

2

O

2-methoxy-3-pyridyl

901

—C≡C—CH

2

O

4-pyridyl

902

—C≡C—CH

2

O

2-chloro-4-pyridyl

903

—C≡C—CH

2

O

2-methoxy-4-pyridyl

904

—C≡C—CH

2

O

2-ethoxy-4-pyridyl

905

—C≡C—CH

2

O

2-methylthio-4-pyridyl

906

—C≡C—CH

2

O

2-trifluoromethyl-5-pyridyl

907

—C≡C—CH

2

O

2-pyrimidinyl

908

—C≡C—CH

2

O

3-pyrimidinyl

909

—C≡C—CH

2

O

4-pyrimidinyl

910

—C≡C—CH

2

O

2-pyrazinyl

911

—C≡C—CH

2

O

3-pyridazinyl

912

—C≡C—CH

2

O

4-pyridazinyl

913

—C≡C—CH

2

O

2-(2H-1,3-oxazinyl)

914

—C≡C—CH

2

O

2-(6H-1,3-oxazinyl)

915

—C≡C—CH

2

O

4-(6H-1,3-oxazinyl)

916

—C≡C—CH

2

O

6-(6H-1,3-oxazinyl)

917

—C≡C—CH

2

O

[1,3,5]-2-triazinyl

918

—C≡C—CH

2

O

[1,2,4]-3-triazinyl

919

—C≡C—CH

2

O

[1,2,4]-5-triazinyl

920

—C≡C—CH

2

O

[1,2,4]-6-triazinyl

The Tables 1-144 below are based on the 4-benzoylpyrazoles of the formula Ib.

Table 1: Compounds 1.1-1.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is methyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 2: Compounds 2.1-2.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is ethyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 3: Compounds 3.1-3.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is n-propyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 4: Compounds 4.1-4.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is methyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 5: Compounds 5.1-5.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is ethyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 6: Compounds 6.1-6.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is n-propyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 7: Compounds 7.1-7.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is methyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 8: Compounds 8.1-8.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is ethyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 9: Compounds 9.1-9.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is n-propyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 10: Compounds 10.1-10.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is methyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 11: Compounds 11.1-11.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is ethyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 12: Compounds 12.1-12.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is n-propyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 13: Compounds 13.1-13.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is methyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 14: Compounds 14.1-14.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is ethyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 15: Compounds 15.1-15.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is n-propyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 16: Compounds 16.1-16.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is methyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 17: Compounds 17.1-17.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is ethyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 18: Compounds 18.1-18.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is n-propyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 19: Compounds 19.1-19.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is methyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 20: Compounds 20.1-20.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is ethyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 21: Compounds 21.1-21.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is n-propyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 22: Compounds 22.1-22.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is methyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 23: Compounds 23.1-23.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is ethyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 24: Compounds 24.1-24.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is chlorine, R

5

is n-propyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 25: Compounds 25.1-25.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is methyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 26: Compounds 26.1-26.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 27: Compounds 27.1-27.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 28: Compounds 28.1-28.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is methyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 29: Compounds 29.1-29.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 30: Compounds 30.1-30.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 31: Compounds 31.1-31.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is methyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 32: Compounds 32.1-32.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 33: Compounds 33.1-33.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 34: Compounds 34.1-34.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is methyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 35: Compounds 35.1-35.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 36: Compounds 36.1-36.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 37: Compounds 37.1-37.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is methyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 38: Compounds 38.1-38.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 39: Compounds 39.1-39.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 40: Compounds 40.1-40.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is methyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 41: Compounds 41.1-41.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 42: Compounds 42.1-42.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 43: Compounds 43.1-43.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is methyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 44: Compounds 44.1-44.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 45: Compounds 45.1-45.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 46: Compounds 46.1-46.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is methyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 47: Compounds 47.1-47.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 48: Compounds 48.1-48.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 49: Compounds 49.1-49.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is methyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 50: Compounds 50.1-50.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 51: Compounds 51.1-51.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 52: Compounds 52.1-52.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is methyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 53: Compounds 53.1-53.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 54: Compounds 54.1-54.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 55: Compounds 55.1-55.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is methyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 56: Compounds 56.1-56.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 57: Compounds 57.1-57.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 58: Compounds 58.1-58.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is methyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 59: Compounds 59.1-59.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 60: Compounds 60.1-60.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 61: Compounds 61.1-61.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is methyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 62: Compounds 62.1-62.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 63: Compounds 63.1-63.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 64: Compounds 64.1-64.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is methyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 65: Compounds 65.1-65.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 66: Compounds 66.1-66.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 67: Compounds 67.1-67.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is methyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 68: Compounds 68.1-68.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 69: Compounds 69.1-69.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 70: Compounds 70.1-70.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is methyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 71: Compounds 71.1-71.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 72: Compounds 72.1-72.920

Compounds of the formula Ib where R

1

is chlorine and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 73: Compounds 73.1-73.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is methyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 74: Compounds 74.1-74.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is ethyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 75: Compounds 75.1-75.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is n-propyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 76: Compounds 76.1-76.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is methyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 77: Compounds 77.1-77.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is ethyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 78: Compounds 78.1-78.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is n-propyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 79: Compounds 79.1-79.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is methyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 80: Compounds 80.1-80.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is methyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 81: Compounds 81.1-81.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is n-propyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 82: Compounds 82.1-82.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is methyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 83: Compounds 83.1-83.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is ethyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 84: Compounds 84.1-84.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is n-propyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 85: Compounds 85.1-85.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is methyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 86: Compounds 86.1-86.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is ethyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 87: Compounds 87.1-87.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is n-propyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 88: Compounds 88.1-88.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is methyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 89: Compounds 89.1-89.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is ethyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 90: Compounds 90.1-90.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is n-propyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 91: Compounds 91.1-91.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is methyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 92: Compounds 92.1-92.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is ethyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 93: Compounds 93.1-93.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is n-propyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 94: Compounds 94.1-94.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is methyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 95: Compounds 95.1-95.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is ethyl and R

5

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 96: Compounds 96.1-96.920

Compounds of the formula Ib where R

1

is methyl and R

2

is chlorine, R

5

is n-propyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 97: Compounds 97.1-97.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is methyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 98: Compounds 98.1-98.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 99: Compounds 99.1-99.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 100: Compounds 100.1-100.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is methyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 101: Compounds 101.1-101.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 102: Compounds 102.1-102.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 103: Compounds 103.1-103.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is methyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 104: Compounds 104.1-104.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 105: Compounds 105.1-105.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 106: Compounds 106.1-106.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is methyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 107: Compounds 107.1-107.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 108: Compounds 108.1-108.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 109: Compounds 109.1-109.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is methyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 110: Compounds 110.1-110.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 111: Compounds 111.1-111.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 112: Compounds 112.1-112.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is methyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 113: Compounds 113.1-113.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 114: Compounds 114.1-114.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 115: Compounds 115.1-115.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is methyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 116: Compounds 116.1-116.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 117: Compounds 117.1-117.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 118: Compounds 118.1-118.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is methyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 119: Compounds 119.1-119.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is ethyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 120: Compounds 120.1-120.920

Compounds of the formula Ib where R

1

is methyl and R

2

is methylsulfonyl, R

5

is n-propyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 121: Compounds 121.1-121.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is methyl and R

5

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 122: Compounds 122.1-122.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 123: Compounds 123.1-123.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is hydrogen and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 124: Compounds 124.1-124.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is methyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 125: Compounds 125.1-125.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 126: Compounds 126.1-126.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is methyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 127: Compounds 127.1-127.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is methyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 128: Compounds 128.1-128.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 129: Compounds 129.1-129.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is ethyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 130: Compounds 130.1-130.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is methyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 131: Compounds 131.1-131.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 132: Compounds 132.1-132.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is methylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 133: Compounds 133.1-133.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is methyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 134: Compounds 134.1-134.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 135: Compounds 135.1-135.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is ethylcarbonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 136: Compounds 136.1-136.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is methyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 137: Compounds 137.1-137.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 138: Compounds 138.1-138.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is methylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 139: Compounds 139.1-139.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is methyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 140: Compounds 140.1-140.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 141: Compounds 141.1-141.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is ethylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 142: Compounds 142.1-142.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is methyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 143: Compounds 143.1-143.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is ethyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

Table 144: Compounds 144.1-144.920

Compounds of the formula Ib where R

1

is methyl and R

2

is trifluoromethyl, R

5

is n-propyl and R

6

is 4-methylphenylsulfonyl and where for each individual compound the substituents X

1

and Het correspond to one line of Table A.

The compounds I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and harmful grasses in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method used, the compounds I, or the compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris

spec.

altissima, Beta vulgaris

spec.

rapa, Brassica napus

var.

napus, Brassica napus

var.

napobrassica, Brassica rapa

var.

silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica

(

Coffea canephora, Coffea liberica

),

Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum

, (

Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium

),

Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum

, Malus spec.,

Manihot esculenta, Medicago sativa

, Musa spec.,

Nicotiana tabacum

(

N. rustica

),

Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies

, Pinus spec.,

Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor

(

s. vulgare

),

Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera

and

Zea mays.

In addition, the compounds I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

The herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The compounds I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend on the intended aims; in any case, they should guarantee a very fine distribution of the active compounds according to the invention.

Essentially, suitable inert auxiliaries include: mineral oil fractions of medium to high boiling point, such as kerosene and animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, eg. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, substituted 4-benzoylpyrazoles, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, eg. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active compounds together with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active compounds I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The compounds I according to the invention can be formulated for example as follows:

I. 20 parts by weight of the compound I are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

II. 20 parts by weight of the compound I are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

III. 20 parts by weight of the active compound I are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

IV. 20 parts by weight of the active compound I are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active compound.

V. 3 parts by weight of the active compound I are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active compound.

VI. 20 parts by weight of the active compound I are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound I is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound I is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (nonionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.

To widen the activity spectrum and to achieve synergistic effects, the substituted 4-benzoylpyrazoles I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF

3

-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds I, alone or else concomitantly in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

The active compound application rates are from 0.001 to 3.0, preferably 0.01 to 1.0 kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

The syntheses of some starting materials and products are described below.

2-Chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)phenyl)-4-sulfonylmethyl-(N-methyl-2-hydroxypyrazole)methanone.

Step a: Methyl 2-chloro-3-bromomethyl-4-sulfonylmethylbenzoate

80 g (0.3 mol) of methyl 2-chloro-3-methyl-4-sulfonylmethylbenzoate in 11 of carbon tetrachloride are heated at 76° C. together with 54 g (0.31 mol) of N-bromosuccinimide and 1.5 g of azoisobutyronitrile for 6 h. The reaction mixture is filtered and freed from the solvent under reduced pressure. Yield: 104 g; m.p. 83-85° C.

Step b: Methyl 2-chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)-4-sulfonylmethylbenzoate

3.3 g of 3,5-dimethylpyrazole and 4.2 g of potassium carbonate in 30 ml of N,N-dimethylformamide are heated at 70° C. for 1 h, admixed with a solution of 10 g (29.3 mmol) of methyl 2-chloro-3-bromomethyl-4-sulfonylmethylbenzoate in 100 ml of N,N-dimethylformamide, and the mixture is heated at 40° C. for 4 h. The reaction mixture is freed from the solvent under reduced pressure, taken up in ethyl acetate and washed with 5% strength aqueous sodium hydroxide solution. The organic phase is dried with sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 10.2 g; m.p. 90-95° C.

Step c: 2-Chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)-4-sulfonylmethylbenzoic acid

9.9 g (26.6 mmol) of methyl 2-chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)-4-sulfonylmethylbenzoate in a mixture of 50 ml of tetrahydrofuran and 50 ml of dist. water are treated at room temperature with 1.3 g of lithium hydroxide for 12 h. The reaction mixture is introduced into 300 ml of dist. water, adjusted to pH 1 using 10% strength aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic phases are dried with sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 6.2 g; m.p. 201-207° C.

Step d: 2-Chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)phenyl)-4-sulfonylmethyl-(N-methyl-2-hydroxypyrazole)methanone

2.0 g (5.6 mmol) of 2-chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)-4-sulfonylmethylbenzoic acid, 0.6 g (5.6 mmol) of N-methyl-5-hydroxypyrazole and 1.4 g of N,N-dicyclohexylcarbodiimide in 50 ml of tetrahydrofuran are heated at 40° C. for 6 h. The reaction mixture is filtered and taken up in ethyl acetate. The organic phase is washed with saturated, aqueous sodium bicarbonate solution, dried with sodium sulfate, filtered and freed from the solvent under reduced pressure.

The crude product, together with 1.2 g of potassium carbonate, in 20 ml of 1,4-dioxane, is heated at 100° C. for 6 h. The reaction mixture is introduced into 500 ml of dist. water and extracted with diethyl ether. The organic phase is adjusted to pH 3 using 10% strength aqueous hydrochloric acid and extracted with dichloromethane. The organic phase is washed with dist. water, dried with sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 1.5 g, m.p. 74° C.

TABLE 145

m.p.

1

H NMR

No.

R

5

R

6

X

1

Het

[° C.]

[ppm]

145.1

CH

3

H

CH

2

O

1-pyrazolyl

160

145.2

CH

3

iso-

CH

2

O

1-pyrazolyl

1.4 (d, 6 H);

propyl

3.4 (s, 3 H);

3.7 (s, 3 H);

5.3 (m, 1 H);

6.1 (s, 2 H);

6.2 (d, 1 H);

7.2 (s, 1 H);

7.3 (s, 1 H);

7.4 (d, 1 H);

7.6 (d, 1 H);

8.2 (d, 1 H)

145.3

CH

3

H

CH

2

O

3,5-di-

74

methyl-1-

pyrazolyl

145.4

CH

3

iso-

CH

2

O

3,5-di-

149

propyl

methyl-1-

pyrazolyl

145.5

CH

3

SO

2

CH

3

CH

2

O

3,5-di-

157

methyl-1-

pyrazolyl

145.6

CH

3

H

CH

2

O

4-chloro-

164

1-pyrazolyl

145.7

CH

3

iso-

CH

2

O

4-chloro-

1.4 (d, 6 H);

propyl

1-pyrazolyl

3.4 (s, 3 H);

3.7 (s, 3 H);

5.3 (m, 1 H);

6.1 (s, 2 H);

7.2 (dd, 2

H);

7.5 (s, 1 H);

7.6 (s, 1 H);

8.2 (d, 1 H)

145.8

CH

3

SO

2

CH

3

CH

2

O

4-chloro-

3.4 (s, 3 H);

1-pyrazolyl

3.6 (s, 3 H);

3.9 (s, 3 H);

6.1 (s, 2 H);

7.2 (s, 1 H);

7.4 (s, 1 H);

7.5 (s, 1 H);

7.6 (d, 1 H);

8.2 (d, 1 H)

145.9

CH

3

H

CH

2

O

2-pyridyl

94

145.10

CH

3

iso-

CH

2

O

2-pyridyl

66

propyl

145.11

C

2

H

5

H

CH

2

O

1-pyrazolyl

63

145.12

C

2

H

5

H

CH

2

O

2-pyridyl

90

USE EXAMPLES

The herbicidal activity of the substituted 4-benzoylpyrazoles of the formula I was demonstrated by greenhouse experiments:

The culture containers used were plastic pots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had een suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

The evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial parts and 0 means no damage, or normal course of growth.

Number	Date	Country
282 944	Sep 1988	EP
9626206	Aug 1996	WO
9703045	Jan 1997	WO
9741105	Nov 1997	WO

Heterocyclic substituted 4-benzoyl-pyrazole as herbicides

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