EA042660B1 - BENZOXABOROL COMPOUNDS - Google Patents

Description

The present invention relates to benzoxaborol compounds and their use as herbicides. The present invention also relates to agrochemical compositions for crop protection and to a method for controlling unwanted vegetation.

Benzoxaboroles of the following formula and their use in the pharmaceutical field are described in Bioorganic & Medicinal Chemistry Letters (2912), 1299-1307.

The use of the above compounds as a herbicide is not mentioned in the cited prior art documents.

Therefore, it is an object of the present invention to provide compounds having improved herbicidal activity, in particular good herbicidal activity at low application rates. In addition, the herbicides must be sufficiently compatible with the crop plants for commercial use.

These and additional objects are achieved by the use of the benzoxaborol compounds of formula (I) as defined below and their agriculturally acceptable salts.

Accordingly, the present invention relates to the use of compounds of formula (I)

where A is a fused saturated or unsaturated 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is selected from the group consisting of H and C ι-Cg-alkyl;

R ² is selected from the group consisting of H and C1-C ₆ alkyl;

R ³ is selected from the group consisting of H, halo, OH, CN, amino, NO ₂ , Ci-Cg-alkyl, C ₃ -C6-alkenyl, C ₃ -C ₆ alkynyl, C1-C ₆ alkoxy, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C1-C ₆ -alkoxy) -C1-C ₆ -alkyl, (C1-C ₆ -alkoxy) -C1-C ₆ -alkoxy, (C1- C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C1-C ₆ -alkoxy)-C ₃ -C ₆ alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or completely halogenated;

R ⁴ is selected from the group consisting of H, halogen, OH, CN, amino, NO ₂ , C1-C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C1-C ₆ alkoxy , C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C1-C ₆ -alkoxy) -C1-C ₆ -alkyl, (C1-C ₆ -alkoxy) -C1-C ₆ -alkoxy, ( C1-C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C1-C ₆ -alkoxy)-C ₃ -C ₆ alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or completely halogenated;

R ⁵ is selected from the group consisting of H, halogen, OH, CN, amino, NO ₂ , Ci-Cg-alkyl, C ₃ -C6-alkenyl, C ₃ -C ₆ alkynyl, C1-C ₆ alkoxy, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C1-C ₆ -alkoxy) -C1-C ₆ -alkyl, (C1-C ₆ -alkoxy) -C1-C ₆ -alkoxy, (C1- C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C1-C ₆ -alkoxy)-C ₃ -C ₆ alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or completely halogenated;

R ⁶ is selected from the group consisting of H, C1-C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, (Ci-C ₆ alkoxy)-C1-C ₆ alkyl, (C1 -C ₆ -alkoxy) -C ₃ -C ₆ -alkenyl, (C1-C ₆ -alkoxy) -C ₃ -C ₆ -alkynyl, phenyl, phenylC1-C ₆ -alkyl, where the aliphatic and phenyl parts of the above radicals are unsubstituted , partially or fully halogenated;

R ⁷ is selected from the group consisting of H, C6-alkyl, _C3 -Cb-alkenyl, _C3 -Cb-alkynyl;

or their agriculturally acceptable salts to control unwanted vegetation.

The present invention also relates to compounds of formula (I)

where A is a fused saturated or unsaturated 4-7 membered carbo cycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members,

R ¹ is selected from the group consisting of H and C ₁ -C ₆ alkyl;

R ² is selected from the group consisting of H and C ₁ -C ₆ alkyl;

R ³ is selected from the group consisting of H, halo, OH, CN, amino, NO2, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ - alkoxy, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -αlkoxy, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy) -C ₃ -C ₆ -alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or fully halogenated;

R ⁴ is selected from the group consisting of H, halogen, OH, CN, amino, NO2, C ₁ -C6 alkyl, C ₃ -C6 alkenyl, C ₃ -C6 alkynyl, C ₁ -C6 alkoxy, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkoxy, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or completely halogenated;

R ⁵ is selected from the group consisting of H, halogen, OH, CN, amino, NO2, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ - alkoxy, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -αlkoxy, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy) -C ₃ -C ₆ -alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or fully halogenated;

R ⁶ is selected from the group consisting of H, C ₁ -C ₆ -alkyl, C ₃ -C ₆ -alkenyl, C ₃ -C ₆ alkynyl, (C ₁ -C ₆ alkoxy) -C ₁ -C ₆ -alkyl , (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy) -C ₃ -C ₆ -alkynyl, phenyl, phenylC ₁ -C ₆ -alkyl, where aliphatic and the phenyl parts of the aforementioned radicals are unsubstituted, partially or fully halogenated;

R ⁷ is selected from the group consisting of H, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl;

or their agriculturally acceptable salts, provided that if A is cyclohexane, R ¹ , R ² , R ³ and R ⁴ are H, R ⁶ is not H or CH ₃ .

The present invention also relates to herbicidal compositions containing a herbicidally active amount of at least one compound (I) as defined above and at least one inert liquid and/or solid carrier.

The present invention also relates to a method for controlling unwanted vegetation which comprises providing a herbicidally effective amount of at least one compound of formula (I) or an agriculturally acceptable salt thereof, as determined to affect the plants, their seeds and/or their habitat. The application can be carried out before, during and/or after, preferably during and/or after the appearance of unwanted vegetation.

Other embodiments of the present invention are obvious from the claims, description and examples. It should be understood that the features mentioned above, which are illustrated below with respect to the subject matter of the invention, may be used not only in the combination indicated in each particular case, but also in other combinations without going beyond the scope of the invention.

Used in this application, the terms struggle and suppression are synonymous.

Used in this application, the terms unwanted vegetation, unwanted plants and harmful plants are synonymous.

In the context of substituents, the term one or more substituents means that the number of substituents is, for example, from 1 to 10, in particular 1, 2, 3, 4, 5, 6, 7 or 8.

If the benzoxaborole compounds of formula (I) as described herein are capable of forming geometric isomers, for example E/Z isomers, the invention relates to both pure isomers and mixtures thereof. In addition, the present invention relates to the use of pure isomers, and to the use of mixtures thereof, and to compositions containing pure isomers or mixtures thereof.

When the benzoxaborole compounds of formula (I) as described herein have one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, the invention relates both to pure enantiomers and to diastereomers and mixtures thereof. In addition, the invention relates to the use of pure enantiomers or diastereomers, and to the use of mixtures thereof, and to compositions containing pure enantiomers or diastereomers or mixtures thereof.

If the benzoxaborole compounds of formula (I) as described herein have ionizable functional groups, they can also be used in the form of their agriculturally acceptable salts. Suitable are, in general, salts of such cations and acid addition salts of those acids whose cations and anions, respectively, do not adversely affect the activity of the active compounds.

Preferred cations are alkali metal ions, preferably lithium, sodium and potassium, alkaline earth metals, preferably calcium and magnesium, and transition metals, preferably manganese, copper, zinc and iron, additionally ammonium and substituted ammonium, in which one to four hydrogen atoms are replaced on C ₁ -C ₄ -alkyl, hydroxy-C ₁ -C ₄ -alkyl, (C ₁ -C ₄ -alkoxy) -C ₁ -C ₄ -alkyl, hydroxy-(C ₁ -C ₄ -alkoxy) -C ₁ -C ₄ -alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt) ions , 2-(2-hydroxyeth-1oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl )ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), in addition, phosphonium ions, sulfonium ions, preferably tri(C1-C ₄ -alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably three (C ₁ -C ₄ -alkyl)sulfoxonium, and, finally, salts of polybasic amines, for example, N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

Anions of useful acid addition salts are mainly chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrophosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, as well as anions of C ₁ -C ₄ -alkanoic acids , preferably formate, acetate, propionate and butyrate.

Other embodiments of the present invention are obvious from the claims, description and examples. It should be understood that the features mentioned above, which are illustrated below with respect to the subject matter of the invention, may be used not only in the combination indicated in each particular case, but also in other combinations without going beyond the scope of the invention.

The organic moieties mentioned in the definition of variables, eg A, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ are, like the term halogen, collective terms for separate listings of individual group members. The term halogen means in each case fluorine, chlorine, bromine or iodine. All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, (alkyl)amino, di(alkyl)amino, alkoxyalkyl, alkoxyalkoxy, (alkyl)carbonyl, (alkoxy)carbonyl chains may be straight chain or branched, and the prefix C _n -Cm denotes in each case the possible number of carbon atoms in the group. The same applies to linked radicals such as cycloalkylalkyl and phenylalkyl. Examples of such values are:

C ₁ -C ₄ -alkyl and also C1-C ₄ -alkyl fragments of C1-C ₄ -alkoxy, C1-C ₄ -alkylthio, C1-C ₄ alkylsulfonyl, (C ₁ -C ₄ -alkyl) carbonyl, (C ₁ -C ₄ -alkyl)carbonyl, (C ₁ -C ₄ -alkoxy)carbonyl, (C ₁ -C ₄ alkyl)carbonyloxy, C1-C ₄ -alkyloxy-C1-C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl -C ₁ -C ₄ -alkyl, (C 1 -C ₄ alkylamino) carbonyl, di (C ₁ -C ₄ -alkyl) aminocarbonyl, (C ₁ -C ₄ -alkylamino) sulfonyl, di (C ₁ -C ₄ alkyl) aminosulfonyl or phenyl-C ₁ -C ₄ -alkyl: for example, CH ₃ , C ₂ H ₅ , n-propyl, CH(CH ₃ ) ₂ , n-butyl, CH(CH3)-C2H ₅ , CH2-CH(CH3 )2 and C(CH3)3;

C ₁ -C ₆ -alkyl and also C ₁ -C ₆ -alkyl fragments of C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkylthio, C1-C6 alkylsulfonyl, (C ₁ -C ₆ -alkyl) carbonyl, (C ₁ -C ₆ -alkyl)carbonyl, (C ₁ -C ₆ -alkoxy)carbonyl, (C ₁ -C ₆ alkyl)carbonyloxy, C1-C ₆ -alkyloxy-C1-C ₆ -alkyl, C ₃ -C ₆ - cycloalkyl-C1-C ₆ -alkyl, phenyl(C1-C ₆ alkyl)aminocarbonyl, (C1-C ₆ -alkylamino)carbonyl, di(C1-C ₆ -alkyl)aminocarbonyl, (C1-C ₆ alkylamino)sulfonyl, di (C1- _C6 -alkyl)aminosulfonyl or phenyl-C1- _C6 -alkyl: C1- _C4 -alkyl as mentioned above and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl , 2,2dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2methylpentyl, 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, 1,1,2trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl -1-methylpropyl or 1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl;

C ₂ -C ₆ -alkenyl and also C ₂ -C ₆ -alkenyl fragments (C1-C ₆ -alkoxy) -C ₂ -C ₆ -alkenyl: linear or branched ethylenically unsaturated hydrocarbon group containing from 2 to 6 carbon atoms , and a C=C double bond at any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl- 1-propenyl, 1-methyl-2-propenyl, 2-methyl2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2methyl-3-butenyl, 3-methyl-3- butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl- 2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4- methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1- dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3- dimethyl-2-butenyl, 1,3dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl3- butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3butenyl, 2-ethyl-1- butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1methyl-2-propenyl, 1-ethyl-2-methyl-1- propenyl and 1-ethyl-2-methyl-2-propenyl;

C ₂ -C ₆ alkynyl and also C ₂ -C ₆ alkynyl fragments (C 1 -C ₆ -alkoxy) -C ₂ -C ₆ alkynyl: a linear or branched unsaturated hydrocarbon group containing from 2 to 6 carbon atoms and co - 3 042660 containing at least one C-C triple bond, such as ethynyl, 1-propynyl, 2-propynyl (propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like;

C1- _C4 haloalkyl: A C1- _C4 alkyl radical as defined above which is partially or wholly substituted by fluorine, chlorine, bromine and/or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlordifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2chloro-2-fluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3- chloropropyl, 2,3dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2- fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1,1,2,2,tetrafluoroethyl and 1-trifluoromethyl-1 ,2,2,2-tetrafluoroethyl;

C ₁ -C 6 -haloalkyl: C 1 -C ₄ -haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;

C ₃ -C ₆ -cycloalkyl: monocyclic saturated hydrocarbons having 3 to 6 ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C1- _C4 alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2methylpropoxy and 1,1-dimethylethoxy;

C ₁ -C ₆ -alkoxy and also C ₁ -C ₆ -alkoxy fragments of (C ₁ -C ₆ -alkoxy)carbonyl, (C1-C6alkoxy)sulfonyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkoxy, (C ₁ -C ₆ -alkoxy) -C ₂ C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy) -C ₂ -C ₆ alkynyl: C 1 -C ₄ -alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2dimethylpropoxy, 2,2- dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2methylpropoxy;

C 1 -C ₄ -haloalkoxy: C ₁ -C ₄ -alkoxy radical as above, which is partially or completely substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy-2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2 ,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3chloropropoxy, 2,3-dichloropropoxy , 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 4-fluorobutoxy, nonafluorobutoxy, 1,1,2 ,2,-tetrafluoroethoxy and 1-trifluoromethyl-1,2,2,2-tetrafluoroethoxy;

C ₁ -C ₆ -haloalkoxy: C1 -C ₄ -alkoxy as mentioned above: C 1 -C ₄ -haloalkoxy as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl , undecafluoropentyl, 6-fluorohexyl, 6-chlorhexyl, 6-bromhexyl, 6-iodohexyl and dodecafluorohexyl;

C ₂ -C ₆ -alkenyloxy: C ₂ -C ₆ -alkenyl, as defined above, which is attached through an oxygen atom, such as ethenyloxy (vinyloxy), 1-propenyloxy, 2-propenyloxy (allyloxy), 1-butenyloxy, 2butenyloxy, 3-butenyloxy 1-methyl-2-propenyloxy and the like;

C ₂ -C ₆ -alkynyloxy: C ₂ -C ₆ -alkynyl, as defined above, which is attached through an oxygen atom, such as ethynyloxy, 1-propynyl, 2-propynyloxy (propargyloxy), 1-butynyloxy, 2butynyloxy, 3-butynyloxy 1-methyl-2-propynyloxy and the like;

(C ₁ -C ₆ -alkoxy)-C ₁ -C ₆ -alkyl: C ₁ -C ₆ -alkyl, in particular C ₁ -C ₄ -alkyl, as defined above, for example methyl, ethyl or isopropyl, where 1 atom hydrogen is replaced by C ₁ -C ₆ alkoxy as defined above, examples include methoxymethyl, ethoxymethyl, n-propoxymethyl, butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-(n-propoxy)ethyl, 1-butoxyethyl, 2- methoxyethyl, 2-ethoxyethyl, 2-(n-propoxy)ethyl, 2-butoxyethyl, 2methoxypropyl, 2-ethoxypropyl, 2-(n-propoxy)propyl, 2-butoxypropyl;

(C ₁ -C ₆ -alkoxy)-C ₁ -C ₆ -alkoxy: C ₁ -C ₆ -alkoxy, in particular C ₁ -C ₄ -alkoxy, as defined above, for example methoxy or ethoxy, where 1 hydrogen atom is replaced on C ₁ -C ₆ alkoxy as defined above, examples include methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, butoxymethoxy, 2methoxyethoxy, 2-ethoxyethoxy, 2-(n-propoxy)ethoxy and 2-butoxyethoxy;

(C ₁ -C ₆ -alkoxy) -C ₂ -C ₆ -alkenyl: C ₂ -C ₆ -alkenyl, in particular C ₂ -C ₄ -alkenyl, as defined above, for example ethenyl, propenyl, 1-butenyl or 2 -butenyl, where 1 hydrogen atom is replaced by C ₁ -C ₆ -alkoxy, as defined above;

(C ₁ -C ₆ alkoxy)-C ₂ -C ₆ alkynyl: C ₂ -C ₆ alkynyl, in particular C ₂ -C ₄ alkynyl, as defined above, for example ethynyl, propynyl or 2-butynyl, where 1 hydrogen atom replaced by C ₁ -C ₆ -alkoxy, as defined above;

phenyl-C ₁ -C ₆ -alkyl: C ₁ -C ₆ -alkyl, in particular C ₁ -C ₄ -alkyl, as defined above, for example methyl

- 4 042660 or ethyl, where 1 hydrogen atom is replaced by phenyl, examples include benzyl, 1-phenylethyl, 2-phenylethyl,

1-phenylpropyl, 2-phenylpropyl, 1-phenyl-1-methylethyl, etc.

The preferred embodiments of the invention mentioned below are to be understood as being preferred either independently or in combination with each other. Specific groups of embodiments of the invention relate to those benzoxaboroles of formula (I), where the variables A, R ¹ , R ² , R ³ , R ⁴ R ⁵ , R ⁶ and R ⁷ either independently of each other or in combination with each other, have the following meanings.

Specific groups of embodiments refer to benzoxaborole compounds of formula (I), where other specific groups of embodiments refer to benzoxaborole compounds of formula (I), where

A is a fused saturated or unsaturated 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is selected from the group consisting of H and C ₁ -C ₆ alkyl;

preferably H, C ₁ -C ₄ alkyl;

in particular H, CH ₃ , CH ₂ CH ₃ ;

especially CH ₃ ;

more specifically H, other specific groups of embodiments refer to benzoxaborole compounds of formula (I) wherein

R ² is selected from the group consisting of H and C ₁ -C ₆ alkyl;

preferably H, C ₁ -C ₄ -alkyl; in particular H, CH ₃ , CH ₂ CH ₃ ;

especially CH3;

more specifically H, other specific groups of embodiments refer to benzoxaborole compounds of formula (I) wherein

R ³ is selected from the group consisting of H, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₂ -(C ₁ -C ₆ -alkoxy)C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy)-C ₁ -C ₆ -alkoxy, where the aliphatic and cycloaliphatic parts of the above radicals are unsubstituted, partially or fully halogenated;

preferably H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₂ -(C ₁ -C ₆ alkoxy)-C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkoxy) -C ₁ -C ₆ -alkoxy, where the aliphatic and cycloaliphatic parts of the above radicals are unsubstituted, partially or fully halogenated;

in particular H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl;

more specifically H, C1, F, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl;

even more specifically H, C1, and F;

especially N,

R ⁴ is selected from the group consisting of H, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₂ -(C ₁ -C ₆ -alkoxy)C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy)-C ₁ -C ₆ -alkoxy, where the aliphatic and cycloaliphatic parts of the above radicals are unsubstituted, partially or fully halogenated;

preferably H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ alkoxy, C ₂ -(C ₁ -C ₆ alkoxy)-C ₁ -C ₆ alkyl, (C ₁ -C ₆ alkoxy) -C ₁ -C ₆ -alkoxy, where the aliphatic and cycloaliphatic parts of the above radicals are unsubstituted, partially or fully halogenated;

in particular H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl;

more specifically H, C1, F, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl;

even more particularly H, C1, F, CF ₃ , CH ₃ ;

especially H, F, C1, CF ₃ ,

R ⁵ is selected from the group consisting of H, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₂ -(C ₁ -C ₆ -alkoxy)C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy)-C ₁ -C ₆ -alkoxy, where the aliphatic and cycloaliphatic parts of the above radicals are unsubstituted, partially or fully halogenated;

preferably H, halogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, (C ₁ -C ₆ alkoxy) -C ₁ -C ₆ -alkoxy, where the aliphatic and cycloaliphatic parts of the above radicals are unsubstituted, partially or fully halogenated;

in particular H, halogen, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl;

more specifically H, C1, F, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl;

even more particularly H, C1, F, CH3;

especially H, C1, F,

R ⁶ is selected from the group consisting of H, C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, phenyl, phenylC1-C6 -alkyl, where the aliphatic and cycloaliphatic parts of the above radicals are unsubstituted, partially or fully halogenated;

preferably H, halogen, C ₁ -C ₄ -alkyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, where the aliphatic and cycloaliphatic parts of the above radicals are unsubstituted, partially or completely halogenated;

in particular H, C1- _C6 alkyl;

more specifically H, C1- _C4 alkyl;

even more specifically H, CH ₃ , CH ₂ CH ₃ ;

especially H, CH ₃ .

Particularly preferred are the benzoxaborole compounds of formula (I) wherein

A is a 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is hydrogen;

R ² is hydrogen;

R ³ is as defined above;

R ⁴ is not H;

R ⁵ is as defined above; And

R ⁶ is H.

Even more preferred are the benzoxaborole compounds of formula (I) wherein

A is a 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is hydrogen;

R ² is hydrogen;

R ³ is as defined above;

R ⁴ is selected from the group consisting of halogen, C1-C ₆ alkyl and C1-C ₆ haloalkyl;

R ⁵ is as defined above; And

R ⁶ is H.

Even more particularly preferred are the benzoxaborole compounds of formula (I) wherein

A is a 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is hydrogen;

R ² is hydrogen;

R ³ is as defined above;

R ⁴ is selected from the group consisting of halogen and C1-C ₆ alkyl;

R ⁵ is as defined above; And

R ⁶ is H.

Particularly particularly preferred are the benzoxaborole compounds of formula (I) wherein

A is a 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is hydrogen;

R ² is hydrogen;

R ³ is as defined above;

R ⁴ is Cl or F;

R ⁵ is as defined above; And

R ⁶ is H.

Also particularly preferred are the benzoxaborole compounds of formula (I) wherein

A is a 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is CH ₃ ;

R ² is hydrogen;

R ³ is as defined above;

R ⁴ is not H;

R ⁵ is as defined above; And

R ⁶ is H.

Even more preferred are the benzoxaborole compounds of formula (I) wherein

A is a 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is CH3;

R ² is hydrogen;

R ³ is as defined above;

- 6 042660

R ⁴ is selected from the group consisting of halogen, C1-C ₆ alkyl and C1-C ₆ haloalkyl;

R ⁵ is as defined above; And

R ⁶ is H.

Even more particularly preferred are the benzoxaborole compounds of formula (I) wherein

A is a 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is CH ₃ ;

R ² is hydrogen;

R ³ is as defined above;

R ⁴ is selected from the group consisting of halogen and C ₁ -C ₆ -alkyl;

R ⁵ is as defined above; And

R ⁶ is H.

Particularly particularly preferred are the benzoxaborole compounds of formula (I) wherein

A is a 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members;

R ¹ is CH ₃ ;

R ² is hydrogen;

R ³ is as defined above;

R ⁴ is Cl or F;

R ⁵ is as defined above; and R ⁶ is H.

Particular preference is given to the benzoxaborole compounds of formula I.a, I.b, I.c, I.d and I.e:

rows of tables A (I.a.A-1.1-I.a.A-1.96).

Table A-2. Compounds of formula Ib, where R ² , R ³ , R ⁴ and R ⁵ are as defined in the lines of the table. A (IbA-2.1-IbA-2.96).

Table A-3. Compounds of formula Ic, where R ² , R ³ , R ⁴ and R ⁵ are as defined in the lines of the table. A (IcA-3.1-IcA-3.96).

Table A-4. Compounds of formula Id, where R ² , R ³ , R ⁴ and R ⁵ are as defined in the lines of the table. A (IdA-4.1-IdA-4.96).

Table A-5. Compounds of formula Ie, where R ² , R ³ , R ⁴ and R ⁵ are as defined in the lines of the table. A (IeA-5.1-IeA-5.96).

Table A-6. Compounds of the formula If, where R ² , R ³ , R ⁴ and R ⁵ are as defined in the lines of the table. A (IfA-6.1-IfA-6.96).

- 7 042660

Table A

No. ^{R2 R3 R4 R6} 1. H H H H 2. SNz H H H 3. H F H H 4. SNz F H H 5. H C1 H H 6. SNz C1 H H 7. H _CF3 H H 8. SNz _CF3 H H 9. H Η F H 10. SNz Η F H AND. H F F H 12. SNz F F H 13. H Cl F H 14. SNz Cl F H 15. H _CF3 F 16. SNz _CF3 F 17. H H Cl H 18. SNz H Cl H 19. H F Cl H 20. SNz F Cl H 21. H Cl Cl H 22. SNz Cl Cl H 23. H _CF3 Cl H 24. SNz _CF3 Cl H 25. H H _CF3 H 26. SNz H _CF3 H 27. H F _CF3 H 28. SNz F _CF3 H 29. H Cl _CF3 H thirty. SNz Cl _CF3 H 31. H _{CF3 CF3} H 32. SNz _{CF3 CF3} H 33. H H H SNz 34. SNz H H SNz 35. H F H SNz 36. SNz F H SNz 37. H Cl H SNz 38. SNz Cl H SNz 39. H _CF3 H SNz 40. SNz _CF3 H SNz 41. H H F SNz 42. SNz H F SNz 43. H F F SNz 44. SNz F F SNz 45. H Cl F SNz 46. SNz Cl F SNz 47. H _CF3 F SNz

- 8 042660

48. CH _{3 CF3} F SNz 49. H H Cl SNz 50. CH ₃ H Cl SNz 51. H F Cl SNz 52. SNz F Cl SNz 53. H C1 Cl SNz 54. SNz C1 Cl SNz 55. H _CF3 Cl SNz 56. SNz _CF3 Cl SNz 57. H Η _CF3 SNz 58. SNz Η _CF3 SNz 59. H F _CF3 SNz 60. SNz F _CF3 SNz 61. H Cl _CF3 SNz 62. SNz Cl _CF3 SNz 63. H _{CF3 CF3} SNz 64. SNz _{CF3 CF3} SNz 65. H H H CH ₂ CH ₃ 66. SNz H H CH ₂ CH ₃ 67. H F H CH ₂ CH ₃ 68. SNz F H CH ₂ CH ₃ 69. H Cl H CH ₂ CH ₃ 70. SNz Cl H CH ₂ CH ₃ 71. H _CF3 H CH ₂ CH ₃ 72. SNz _CF3 H CH ₂ CH ₃ 73. H H F CH ₂ CH ₃ 74. SNz H F CH ₂ CH ₃ 75. H F F CH ₂ CH ₃ 76. SNz F F CH ₂ CH ₃ 77. H Cl F CH ₂ CH ₃ 78. SNz Cl F CH ₂ CH ₃ 79. H _CF3 F CH ₂ CH ₃ 80. SNz _CF3 F CH ₂ CH ₃ 81. H H Cl CH ₂ CH ₃ 82. SNz H Cl CH ₂ CH ₃ 83. H F Cl CH ₂ CH ₃ 84. SNz F Cl CH ₂ CH ₃ 85. H Cl Cl CH ₂ CH ₃ 86. SNz Cl Cl CH ₂ CH ₃ 87. H _CF3 Cl CH ₂ CH ₃ 88. SNz _CF3 Cl CH ₂ CH ₃ 89. H H _CF3 CH ₂ CH ₃ 90. SNz H _CF3 CH ₂ CH ₃ 91. H F _CF3 CH ₂ CH ₃ 92. SNz F _CF3 CH ₂ CH ₃ 93. H Cl _CF3 CH ₂ CH ₃ 94. SNz Cl _CF3 CH ₂ CH ₃ 95. H _{CF3 CF3} CH ₂ CH ₃ 96. SNz _{CF3 CF3} CH ₂ CH ₃

The benzoxaborole compounds of formula (I) according to the invention can be prepared using standard organic chemistry methods, for example the following methods.

Annelated benzaldehydes corresponding to (II) are known (e.g. CAS numbers 42080237-5, 137987-77-0, 2089861-40-3, 2092080-77-6, 2110359-08-3, 857081-99-3) or can be obtained by analogy with the methods described for known examples.

Benzaldehyde borols of formula (IV) where A, R ³ , R ⁴ , R ⁶ and R are as defined above can be prepared by reacting benzaldehyde (II) where X is OSO2CF3, Cl, Br or I , with tetraalkoxydiborane as shown in the following Scheme 1.

- 9 042660

Scheme 1.

The reaction can be carried out analogously to known procedures (Miyaura borylation; see for example: Li, Pengbin et al., Organic & Biomolecular Chemistry, 12(22), 3604-3610; 2014. Fang, Hao et al., Tetrahedron Letters, 46(10 ), 1671-1674; 2005).

Various tetraalkoxydiboranes can be used, preferably 4,4,4',4',5,5,5',5'octamethyl-2,2'-bi-1,3,2-dioxaborolane or 5,5,5', 5'-tetramethyl-2,2'-bi-1,3,2-dioxaborinan.

The reaction is usually carried out at a temperature in the range between 20-100°C in an inert organic solvent. Preferably the reaction is carried out at a temperature in the range between 0-100°C.

The reaction can be carried out at atmospheric pressure or at elevated pressure, optionally under an inert gas atmosphere, continuously or intermittently.

In one embodiment of the process according to the invention, the benzaldehyde of formula (II) with the tetraalkoxydiborane of formula (III) is used in equimolar amounts.

In another embodiment of the method according to the invention, the tetraalkoxydiborane of formula (III) is used in excess relative to the benzaldehyde of formula (II).

Preferably, the molar ratio of tetraalkoxydiborane of formula (III) to benzaldehyde of formula (II) is in the range from 2:1 to 1:1, preferably from 1.5:1 to 1:1, particularly preferably 1.2:1.

The reaction of a benzaldehyde of formula (II) with a tetraalkoxydiborane of formula (III) is usually carried out in an organic solvent. In principle, all solvents are suitable which are capable of dissolving the benzaldehyde of the formula (II) and the tetraalkoxydiborane of the formula (III) at least partially and preferably completely under the reaction conditions. Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C ₅ -C ₈ alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters, such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3dimethyl-2-imidazolidinone (DMI), N ,N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP). The preferred solvent is DMF as defined above.

The term solvent as used in this application also includes mixtures of two or more of the above compounds.

The reaction of benzaldehyde of formula (II) and tetraalkoxydiborane of formula (III) is usually carried out in the presence of a base. Examples of suitable bases include metal bases and nitrogen bases. Examples of suitable metal-containing bases are inorganic compounds such as alkali and alkaline earth metal hydroxides, and other metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxide and other metal oxides such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal formates, acetates and other metal salts of carboxylic acids such as sodium formate, sodium benzoate, lithium acetate, sodium acetate , potassium acetate, magnesium acetate and calcium acetate; alkali and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate and calcium carbonate, as well as alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as sodium phosphate, potassium phosphate and calcium phosphate; alkali and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium t-butoxide, potassium t-pentoxide and dimethoxymagnesium; and, in addition, organic bases such as tertiary amines such as tri-C ₁ -C ₆ -alkylamines, for example triethylamine, trimethylamine, Nethyldiisopropylamine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N- methylmorpholine; and also bicyclic amines such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN). Preferred bases are alkoc

- 10 042660 Alkali and alkaline earth metal oxides as defined above. The term base as used in this application also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base. The bases can be used in excess, preferably 1 to 10, particularly preferably 2 to 4 basic equivalents, based on the benzaldehyde of formula (II), and they can also be used as a solvent.

The reaction of benzaldehyde of formula (II) and tetraalkoxydiborane of formula (III) is carried out in the presence of a catalyst. Examples of suitable catalysts are palladium complexes such as tetrakistriphenylphosine palladium, 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(I), dichlorobis(triphenylphosphine)palladium or palladium acetate.

Preferably, the molar ratio of the benzaldehyde of formula (II) to the palladium catalyst is in the range of 10:1 to 1000:1, preferably 120:1 to 100:1, particularly preferably 50:1.

A skilled worker using conventional methods can easily determine the end of the reaction.

The reaction mixtures are worked up in the usual manner, for example by mixing with water, phase separation and, if necessary, chromatographic purification of the crude product.

The benzaldehyde boroles of formula (IV) can be converted to the corresponding benzoxaboroles (I) as shown in the following Scheme 2.

Scheme 2.

(IV) (I)

The reaction can be carried out similarly to known techniques (e.g., Zhang, Yong-Kang et al., Journal of Medicinal Chemistry, 60(13), 5889-5908; 2017. Jacobs, Robert T. et al., Future Medicinal Chemistry, 3(10 ), 1259-1278; 2011. Wienhold, Falk et al., Synthesis, (24), 4059-4067; 2011).

For R ² =H, a reducing agent is used, preferably NaBH4, LiBH4, LiAlH4.

The reaction is usually carried out at a temperature in the range from 0 to 100°C in an inert organic solvent.

The reaction can be carried out at atmospheric pressure or at elevated pressure, if necessary, in an inert gas atmosphere, continuously or intermittently.

In one embodiment of the method according to the invention, the benzaldehyde borole of formula (IV) with the reducing agent is used in equimolar amounts.

In another embodiment of the process according to the invention, the reducing agent is used in excess with respect to the benzaldehyde borols of formula (IV).

Preferably, the molar ratio of reducing agent to benzaldehyde borols of the formula (IV) is in the range of 2:1 to 1:1, preferably 1.5:1 to 1:1, particularly preferably 1.2:1.

The reaction of benzaldehydeborols of formula (IV) with a reducing agent is usually carried out in an organic solvent. In principle, all solvents are suitable which are capable of dissolving the benzaldehyde borols of the formula (IV) and the reducing agent at least partially and preferably completely under the reaction conditions. Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of C ₅ -C ₈ alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), as well as dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N-dimethylformamide (DMF), N,N- dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO), and 1-methyl-2-pyrrolidinone (NMP). The preferred solvent is THF as defined above. The term solvent as used herein also includes mixtures of two or more of the above compounds.

A skilled worker using conventional methods can easily determine the end of the reaction.

The reaction mixtures are worked up in the usual manner, for example by mixing with water, phase separation and, if necessary, by chromatographic purification of the crude product.

For R ² =C ₁ -C ₄ alkyl, an alkylating agent is used, preferably magnesium methyl bromide, ethyl magnesium bromide, methyl lithium, ethyl lithium.

- 11 042660

The reaction is usually carried out at a temperature in the range from 0 to 100°C in an inert organic solvent.

The reaction can be carried out at atmospheric pressure or at elevated pressure, if necessary, in an inert gas atmosphere, continuously or periodically.

In one embodiment of the process according to the invention, the benzaldehyde borole of formula (IV) with the alkylating agent is used in equimolar amounts.

In another embodiment of the process according to the invention, the alkylating agent is used in excess with respect to the benzaldehyde borols of formula (IV).

Preferably, the molar ratio of alkylating agent to benzaldehyde borols of formula (IV) is in the range of 2:1 to 1:1, preferably 1.5:1 to 1:1, particularly preferably 1.2:1.

The reaction of benzaldehydeborols of formula (IV) with an alkylating agent is usually carried out in an organic solvent. In principle, all solvents are suitable which are capable of dissolving the benzaldehyde borols of formula (IV) and the alkylating agent at least partially and preferably completely under the reaction conditions. Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of C ₅ -C ₈ alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, (TBME), dioxane, anisole and tetrahydrofuran (THF), as well as dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N-dimethylformamide (DMF), N,N -dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP). The preferred solvent is THF as defined above. The term solvent as used herein also includes mixtures of two or more of the above compounds.

A skilled worker using conventional methods can easily determine the end of the reaction.

The reaction mixtures are worked up in the usual manner, for example by mixing with water, phase separation and, if necessary, chromatographic purification of the crude product.

The compounds of formula (I) have herbicidal activity. Therefore, they can be used to control unwanted plants or unwanted vegetation. They can also be used in a method for controlling undesirable vegetation or undesirable plants which provides for the action of at least one compound of formula (I) or a salt thereof on the plants, their environment or seeds. To ensure that a compound of formula (I) or a salt thereof has an effect on the plants, their media or seeds, the compounds of the invention are applied to the plants, their media or the seeds of said plants.

To expand the spectrum of action and to achieve synergistic effects, the benzoxaborole compounds of formula (I) can be mixed with a large number of representatives of other herbicidal or growth-regulating groups of active ingredients, and then applied simultaneously.

Suitable components for mixtures are, for example, herbicides from the classes of acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, hydroxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoramidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, ) benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, uracils, urea.

The compounds of formula (I) can also be used in combinations of benzoxaborole compounds of formula (I) with at least one additional herbicide B and/or at least one safener C).

Additional herbicidal compound B (component B) is specifically selected from the herbicides of class b1)-b15):

b1) inhibitors of lipid biosynthesis;

b2) acetolactate synthase inhibitors (ALS inhibitors);

b3) photosynthesis inhibitors;

b4) protoporphyrinogen-IX oxidase inhibitors;

b5) bleaching herbicides;

b6) enolpyruvylshikimate-3-phosphate synthase inhibitors (EPSP inhibitors);

b7) glutamine synthetase inhibitors;

b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

- 12 042660 b9) inhibitors of mitosis;

b10) very long chain fatty acid synthesis inhibitors (VLCFA inhibitors);

b11) cellulose biosynthesis inhibitors;

b12) uncoupling herbicides;

b13) auxin herbicides;

b14) auxin transfer inhibitors; and b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumiluron, dalapon, dazomet, difenzoquat, diphenzoquat methyl sulfate, dimethipine, DSMA, dimron, endothal and its salts, etobenzanide, flamprop, flamprop- isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanophane, indaziflam, maleic hydrazide, mefluidide, metam, methiozoline (CAS 403640-27- 7), methyl azide, methyl bromide, methyldymron, methyl iodide, MSMA, oleic acid, oxaziclomefon, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphan, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters, including their agriculturally acceptable salts or derivatives such as ethers, esters or amides.

Preference is given to those compositions according to the present invention which contain at least one herbicide B selected from herbicides of the classes b1, b6, b9, b10 and b11.

Examples of herbicides B which can be used in combination with compounds of formula (I) in accordance with the present invention are:

b1) from the group of lipid biosynthesis inhibitors:

ACC herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cyclooxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-R, fenoxaprop-R- ethyl, fluazifop, fluazifop-butyl, fluazifop-R, fluazifop-R-butyl, haloxyfop, haloxifop-methyl, haloxyfop-R, haloxifop-P-methyl, methamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop- tefuryl, quizalofop-R, quizalofop-R-ethyl, quizalofop-R-tefuryl, setoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3 -yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H) -one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1,1'biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)- dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl -2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6tetramethyl-2H -pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl] -3 -yl)-3,6-dihydro2,2,6,6-tetramethyl- 2H-pyran-3-one (CAS 1312340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H -pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5 methyl ester -oxo-2Hpyran-3-yl-carbonic acid (CAS 1312337-51-1); methyl ester 4-(2',4'-dichloro-4cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl-carbonic acid; 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6tetramethyl-5-oxo methyl ester -2H-pyran-3-yl-carbonic acid (CAS 1312340-83-2); methyl ester 4(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl-carbonic acid (CAS 1033760-58-5); and non-ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, etofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, thiocarbazil, triallate and vernolate;

b2) from the group of ALS inhibitors:

sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuronmethyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, etametsulfuron, etametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, halosulfuron methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl sodium, jofensulfuron, jofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primesulfuron, primesulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, ethyl sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron, imidazolinones such as imazamethabenz, imazametabenz-methyl, imazamox, imazapic, imazametabenz-methyl, imazamox, imazapic, imazapyr, and imazamox imazetapir, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, methosulam, penoxulam, pyrimisulfan and pyroxulam,

- 13 042660 pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxime, pyrifthalide, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 1-methylethyl ester 4[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl] propyl ester amino]-benzoic acid (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8), sulfonylaminocarbonyl- triazolinon herbicides such as flucarbazone, flucarbazone sodium, propoxycarbazone, propoxycarbazone sodium, thiencarbazone, and thiencarbazone-methyl; and triafamone;

among them, a preferred embodiment of the invention relates to those compositions containing at least one imidazolinone herbicide, amicarbazone, photosystem II inhibitors, for example -(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4methoxy-3-methyl- 2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455 -12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5 -tert-butyl-1-methylpyrazol-3-yl)-4-chloro-2hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methylpyrazol-3 -yl)-3-chloro-2hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4(trifluoromethyl)- 2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4 -hydroxy-1-methyl-3-[4(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4(trifluoromethyl)-2 -pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1), triazine herbicides, in including chlortriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametrin, atrazine, chloridazone, cyanazine, desmetrin, dimethamethrin, hexazinon, metribuzin, promethone, prometrin, propazine, simazine, symetrin, terbumetone, terbutylazine, terbutrin and trietazine, arylurea, such as chlorbromuron, chlortoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, metabenzthiazuron, methobenzuron, methoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates such as desmedipham, carbutylate, phenmedipham, , nitrile herbicides such as bromphenoxime, bromoxynil and its salts and esters, ioxynil and its salts and esters, uracils such as bromacil, lenacil and terbacil and bentazon and bentazone sodium, pyridate, pyridafol, pentanochlor and propanil and inhibitors photosystem I such as diquat, diquat dibromide, paraquat, paraquat dichloride and paraquat dimethyl sulfate. Among them, the preferred embodiment of the invention relates to those compositions that contain at least one aryl urea herbicide. Among them, also a preferred embodiment of the invention relates to those compositions that contain at least one triazine herbicide. Among them, also a preferred embodiment of the invention relates to those compositions that contain at least one nitrile herbicide;

b4) from the group of inhibitors of protoporphyrinogen-IX oxidase: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendison, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxifen, chlorphthalim, cynidone-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazine, fluoroglycofen, fluoroglycophen-ethyl, flutiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazon, profluazol, pyraclonil, pyraflufen, pyraflufenethyl, saflufenacil, sulfentrazone, thiadiazimine, thiadiazimine trifludimoxazine, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy ]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9) , N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6- fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl -1Hpyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2Hbenzo[1,4]oxazine- 6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7trifluoro-3-oxo -4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3dione (CAS 1300118-96-0 ), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro2H-benzo[1,4]oxazin-6-yl )-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro5-(difluoromethoxy)-1H-methylpyrazol-3-yl ]-4-fluoro-phenoxy]-3-methoxybut-2-enoate (CAS 948893-00-3), and 3-[7-Chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazole-4- yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimidine 2,4-dione (CAS 212754-02-4);

b5) from the group of bleaching herbicides:

PDS inhibitors: beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazone, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-337), HPPD inhibitors: benzobicyclone, benzofenap, bicyclopyrone, chlomazone, fenquinotrion, isoxaflutol, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotol, pyrazolinate, pyrazoxyfen, sulcot- 14 042660 rion, tefuryltrione, tembotrione, tolpyralate, topramesone, whitening, with unknown purpose: aclonifen, amitrol, flumeturon, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4(trifluoromethyl)benzamide (CAS 1361139-71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl -3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81778-66-7);

b6) from the group of EPSP synthase inhibitors:

glyphosate, glyphosate isopropylammonium, glyphosate potassium and glyphosate trimesium (sulfosate);

b7) from the group of glutamine synthase inhibitors:

bilanafos (bialaphos), bilanafos-sodium, glufosinate, glufosinate-R and glufosinate-ammonium;

b8) from the group of DHP synthase inhibitors:

asulam;

b9) from the group of mitosis inhibitors:

compounds of the K1 group: dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as amiprofos, amiprofos-methyl and butamiphos, benzoic acid herbicides such as chlorthal, chlorthaldimethyl, pyridines, such as dithiopyr and thiazopyr; benzamides such as propizamide and tebutam; compounds of group K2: carbetamide, chlorprofam, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and profam; among them, compounds of group K1, in particular dinitroanilines are preferred;

b10) from the group of VLCFA inhibitors:

chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-R, metazachlor, metolachlor, metolachlor-C, petoxamide, pretilachlor, propachlor, propisochlor and tenylchlor, hydroxyacetanilides such as fluphenacet and mefenacet, acetanilides such as diphenamide, naproanilide, napropamide and napropamide-M, tetrazolinones such as fentrazamide and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of formulas II.1, II.2, II.3, II .4, II.5, II.6, II.7, II.8 and II.9

NCH.

NCH.

N-CH isoxazoline compounds of formula .N'n-ch.

N' ochf ₂

N-CH ₃

OCHF, (II) are known in the art, for example from WO

2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576, among VLCFA inhibitors, preference is given to chloroacetamides and hydroxyacetamides;

b11) from the group of cellulose biosynthesis inhibitors:

chlorthiamide, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5pentafluorophenyloxy-1 ⁴ -[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1);

b12) from the group of uncoupling herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of auxin herbicides:

2,4-D and its salts and esters such as claciphos, 2,4-DB and its salts and esters, amino

- 15 042660 nocyclopyrachlor and its salts and esters, aminopyralide and its salts such as aminopyraliddimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazoline, benazoline-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-R and its salts and esters, flopirauxifen, fluroxypyr, fluroxypyrbutomethyl, fluroxypyrmeptyl, galauxifen and its salts and esters ethers (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MSRV and its salts and esters, mecoprop and its salts and esters, mecoprop-R and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6 -(7-fluoro-1H-indol-6yl)picolinic acid (CAS 1629965-65-6);

b14) from the group of auxin transfer inhibitors:

diflufenzopyr, diflufenzopyr sodium, naptalam and naptalam sodium;

b15) from the group of other herbicides:

bromobutide, chlorflurenol, chloroflurenol-methyl, cinmethylin, cumiluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, diphenzoquat-methyl sulfate, dimethipine, DSMA, dimron, endotal and its salts, etobenzanide , flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine ammonium, indanophane, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyldimron, methyl iodide, MSMA, oleic acid, oxacyclomefone, pelargonic acid, pyributicarb, quinoclamine and tridifan.

Preferred herbicides B which can be used in combination with compounds of formula (I) and especially compounds I.a, I.b, I.c, I.d and I.e according to the present invention are:

b1) from the group of lipid biosynthesis inhibitors:

cletodim, clodinafop-propargyl, cycloxidim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, methamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, quizalofop-P- tefuryl, setoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl- 2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2Hpyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6tetramethyl-2H-pyran-3(6H) -one (CaS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl -2H-pyran-3-one (CAS 1312337-48-6); 5(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl- 2Npiran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6- tetramethyl2H-pyran-3-one (CAS 1312340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6dihydro-2,2,6,6-tetramethyl-2Н- pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo methyl ester -2H-pyran-3-ylcarbonic acid (CAS 1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo methyl ester -2H-pyran-3-yl-carbonic acid; 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5 methyl ester -oxo-2Hpyran-3-yl-carbonic acid (CAS 1312340-83-2); methyl ester 4-(2',4'-dichloro-4-ethyl[1,1'biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl-carbonic acid (CAS 103376058-5); benfuresate, dimepiperate, EPTC, esprocarb, etofumesate, molinate, orbencarb, prosulfocarb, thiobencarb and triallate;

b2) from the group of ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, etametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl sodium, halosulfuron-methyl, imazametabenz-methyl, imazamox, imazapik, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron methyl sodium, jofensulfuron, jofensulfuron sodium, mesosulfuron, metazosulfuron, methosulam, metsulfuron-methyl, nicosulfuron, orthoxsulfuron, primethyl propoxycarbazone-sodium, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxime, pyrimisulfan, pyrifthalide, pyriminobac-methyl, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron and triafamone;

b3) from the group of photosynthesis inhibitors:

ametrine, amicarbazone, atrazine, bentazon, bentazon sodium, bromoxynil and its salts and esters, chloridazone, chlortoluron, cyanazine, desmedifam, diquat-dibromide, diuron, fluometuron, hexazinon, ioxynil and its salts and esters, isoproturon, lenacil, linuron, metamitron, metabenzthiazuron, metribuzin, paraquat, paraquat dichloride, phenmedipham, propanil, pyridate, simazine, terbutrin,

- 16 042660 terbutylazine, thidiazuron, 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5one (CAS 1654744-66-7), 1-( 5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3- yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl) -4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-3 -chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2- pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy- 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl )-2-pyridyl]imidazolidin-2-one (CAS 170808722-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2- he (CAS 2023785-80-8) and 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1);

b4) from the group of protoporphyrinogen-IX oxidase inhibitors:

acifluorfen sodium, bencarbazone, benzfendison, butafenacil, carfentrazoneethyl, cinidoneethyl, flufenpyethyl, flumiclorac-pentyl, flumioxazine, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen-ethyl, sulfenacyl, saflufenacil, saflufenacil, saflufenacil, trifludimoxazine, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy ] acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92- 9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2- chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5methyl -1 H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2Hbenzo[1,4 ]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7trifluoro- 3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3dione (CAS 1300118-96-0); 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro2H-benzo[1,4]oxazin-6-yl)- 1H-pyrimidin-2,4-dione (CAS 1304113-05-0) and 3-[7-chloro-5-fluoro-2(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-( trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4);

b5) from the group of bleaching herbicides:

aclonifen, amitrol, beflubutamide, benzobicyclone, bicyclopyrone, clomazone, diflufenican, fenquinotrion, flumeturon, flurochloridone, flurtamone, isoxaflutol, mesotrione, oxotrione (CAS 1486617-21-3), norflurazone, picolinafen, pyrasulfotol, pyrazolinate, tefuryltrione, tefuryltrione, sulcotrione tolpyralate, topramesone, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4 -(trifluoromethyl)benzamide (CAS 1361139-71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5dichlorophenyl) methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);

b6) from the group of EPSP synthase inhibitors:

glyphosate, glyphosate isopropylammonium, glyphosate potassium and glyphosate trimesium (sulfosate);

b7) from the group of glutamine synthase inhibitors:

glufosinate, glufosinate-P, glufosinate-ammonium;

b8) from the group of DHP synthase inhibitors:

asulam;

b9) from the group of mitosis inhibitors:

benfluralin, dithiopyr, ethalfluralin, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, oryzalin, pendimethalin, thiazopyr and trifluralin;

b10) from the group of VLCFA inhibitors:

acetochlor, alachlor, amidochlor, anilophos, butachlor, cafentrol, dimethenamid, dimethenamid-R, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretylachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone tenylchlor, and isoxazoline - compounds of formula II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as above;

b11) from the group of cellulose biosynthesis inhibitors:

dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5pentafluorophenyloxy-1 ⁴ -[1,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1);

b13) from the group of auxin herbicides:

2,4-D and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters , dicamba and its salts and esters, dichlorprop-P and its salts and esters, flopirauxifen, fluroxypyrmeptyl, galauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MSRV and its salts and esters, mecoprop-R and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen,

- 17 042660 floropyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6yl)picolinic acid (CAS 1629965-65-6) ;

b14) from the group of auxin transfer inhibitors:

diflufenzopyr and diflufenzopyr sodium;

b15) from the group of other herbicides:

bromobutide, cinmethylin, cumiluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, difenzoquat, difenzoquat-methyl sulfate, DSMA, dimron (=daimuron), indanophane, metam, methyl bromide, MSMA, oxaziclomefon, pyributicarb and tridifan.

Active Compounds B and C having a carboxyl group can be used as an acid, as an agriculturally acceptable salt as defined above, or as an agriculturally acceptable derivative in the compositions according to the invention.

In the case of dicamba, suitable salts include salts where the counterion is an agriculturally useful cation. For example, suitable dicamba salts are dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicambadiglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba-N,N-bis-(3aminopropyl )methylamine and dicamba-diethylenetriamine. Examples of suitable esters are dicamba-methyl and dicamba-butyl.

Suitable 2,4-D salts are 2,4-O-ammonium, 2,4-O-dimethylammonium, 2,4-Ddiethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2, 4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammonium, 2,4D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-Dtris(isopropyl)ammonium, 2,4-O-trolamine, 2,4-D-lithium, 2,4-O-sodium. Examples of suitable 2,4-D esters are 2,4-D-butyl, 2,4-D-2-butoxypropyl, 2,4-O-3-butoxypropyl, 2,4-D-butyl, 2,4-O -ethyl, 2,4-O-ethylhexyl, 2,4-D-isobutyl, 2,4-O-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-O-methyl , 2,4-D-octyl, 2,4-O-pentyl, 2,4-O-propyl, 2,4-O-tefuryl and clasiphos.

Suitable salts of 2,4-DB are, for example, 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethylammonium. Suitable 2,4-DB esters are, for example, 2,4-DB-butyl and 2,4DB-isoctyl.

Suitable salts of dichloroprop are, for example, dichloroprop-sodium, dichloropropotassium and dichloroprop-dimethylammonium. Examples of suitable dichloroprop esters are dichloroprop-butyl and dichloroprop-isoctyl.

Suitable salts and esters of MCPA include MCPA-butyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isooctyl, MCPA-isopropyl, MCPA-isopropylammonium , MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.

A suitable salt of MSRP is sodium MSRP. A suitable ester of MSRV is MSRV-ethyl.

Suitable salts of clopyralide are clopyralide-potassium, clopyralide-olamine and clopyralide-tris-(2-hydroxypropyl)ammonium. An example of suitable clopyralid esters is clopyralid-methyl.

Examples of suitable fluroxypyr esters are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1-methylethyl, where fluroxypyr-meptyl is preferred.

Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable picloram ester is picloram-isooctyl.

A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are, for example, triclopyr-ethyl and triclopyr-butotyl.

Suitable salts and esters of chloramben include chloramben ammonium, chloramben diolamine, chloramben methyl, chloramben methyl ammonium and chloramben sodium. Suitable salts and esters of 2,3,6TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium and 2,3,6-TBA-sodium .

Suitable salts and esters of aminopyralide include aminopyralid-potassium, aminopyralid-dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.

Suitable glyphosate salts are, for example, ammonium glyphosate, diammonium glyphosate, dimethylammonium glyphosate, isopropylammonium glyphosate, potassium glyphosate, sodium glyphosate, trimesium glyphosate, as well as ethanolamine and diethanolamine salts, preferably diammonium glyphosate, isopropylammonium glyphosate and trimesium glyphosate. (sulfosate).

A suitable glufosinate salt is, for example, ammonium glufosinate.

A suitable salt of glufosinate-P is, for example, glufosinate-P-ammonium.

Suitable salts and esters of bromoxynil are, for example, bromoxynyl butyrate, bromoxynyl heptanoate, bromoxynyl octanoate, bromoxynyl potassium and bromoxynyl sodium.

Suitable salts and esters of ioxonyl are, for example, ioxonyl octanoate, ioxonyl potassium and ioxonyl sodium.

- 18 042660

Suitable salts and esters of mecoprop include mecoprop-butyl, mecopropdimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isooctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium, and mecoprop-trolamine.

Suitable salts of mecoprop-P are, for example, mecoprop-P-butyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P sodium.

A suitable salt of diflufenzopyr is, for example, diflufenzopyr sodium.

A suitable naptalam salt is, for example, sodium naptalam.

Suitable salts and esters of aminocyclopyrachlor are, for example, aminocyclopyrachloro-dimethylammonium, aminocyclopyrachloro-methyl, aminocyclopyrachlorotriisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachloro-potassium.

A suitable salt of quinclorac is, for example, quinclorac-dimethylammonium.

A suitable salt of quinmerac is, for example, quinmerac-dimethylammonium.

A suitable imazamox salt is, for example, imazamox ammonium.

Suitable imazapic salts are, for example, imazapic ammonium and imazapicisopropylammonium.

Suitable salts of imazapyr are, for example, imazapyr ammonium and imazapyrisopropylammonium.

A suitable imazaquin salt is, for example, imazaquin ammonium.

Suitable imazethapyr salts are, for example, imazethapyr ammonium and imazethapyrisopropylammonium.

A suitable salt of topramesone is, for example, topramesone sodium.

Particularly preferred herbicidal compounds B are herbicides B as defined above; in particular, herbicides B.1-B.202, listed below in table. IN:

Table B

Herbicide B Herbicide B IN 1 cletodym B.19 bensulfuron-methyl AT 2 clodinafop-propargyl IN 20 bispyribac-sodium v.z cyclooxydim AT 21 cloransulam-methyl AT 4 cyhalofop-butyl B.22 chlorsulfuron AT 5 fenoxaprop-ethyl B.23 clorimuron AT 6 fenoxaprop-P-ethyl B.24 cyclosulfamuron AT 7 metamythop B.25 diclosulam AT 8 pinoxaden B.26 florasulam AT 9 profoxidim B.27 flumetsulam AT 10 setoxydim B.28 flupyrsulfuron-methyl- in and tepraloxydim sodium AT 12 tralkoxydim B.29 foramsulfuron B.13 esprocarb B.30 imazamox B.14 etofumesate B.31 imazamox-ammonium B.15 molinate B.32 imazapic B.16 prosulfocarb B.33 imazapic-ammonium B.17 thiobencarb B.34 imazapic- B.18 triallat isopropylammonium B.35 imazapyr

- 19 042660

B.36 imazapyr-ammonium B.37 imazapyrisopropylammonium B.38 imazaquin B.39 imazaquin-ammonium B.40 imazethapyr B.41 imazethapyr-ammonium B.42 imazetapyrisopropylammonium B.43 imazosulfuron B.44 iodsulfuron-methyl sodium B.45 iofensulfuron B.46 iofensulfuron-sodium B.47 mesosulfuron-methyl B.48 metazosulfuron B.49 metsulfuron-methyl B.50 methosulam B.51 nicosulfuron B.52 penoxsulam B.53 propoxycarbazone sodium B.54 pyrazosulfuron-ethyl B.55 pyribenoxime B.56 pyrophthalide B.57 pyroxsulam B.58 propyrisulfuron B.59 rimsulfuron B.60 sulfosulfuron B.61 thiencarbazone-methyl B.62 thifensulfuron-methyl B.63 tibenuron-methyl B.64 tritosulfuron B.65 triaphamon B.66 ametrine B.67 atrazine B.68 bentazon B.69 bromoxynil B.70 bromoxynyl octanoate B.71 bromoxynyl heptanoate B.72 bromoxynil-potassium B.73 diuron B.74 fluometuron B.75 hexazinon B.76 isoproturon B.77 linuron B.78 metamitron B.79 metribuzin B.80 propanil

B.81 simazine B.82 terbutylazine B.83 terbutrin B.84 paraquat dichloride B.85 acifluorfen B.86 butafenacil B.87 carfentrazone-ethyl B.88 flumioxazine B.89 fomesafen B.90 oxadiargyl B.91 oxyfluorfen B.92 pyraflufen B.93 pyraflufen-ethyl B.94 saflufenacil B.95 sulfentrazone B.96 trifludimoxazine B.97 ethyl [3-[2-chloro-4-fluoro-5(1-methyl-6-trifluoromethyl2,4-dioxo-1,2,3,4- tetrahydropyrimidin-3yl)phenoxy]-2- pyridyloxy]acetate (CAS 353292-31-6) B.98 benzobicyclone B.99 bicyclopyrone B.100 clomazone B.101 diflufenican B.102 flurochloridone B.103 isoxaflutol B.104 mesotrione B.105 norflurazon B.106 picolinafen B.107 sulcotrione B.108 tefuryltrione B.109 tembotrione B.110 tolpyralate B.111 toprameson B.112 topramesone-sodium V.IZ amitrol B.114 fluometuron B.115 fenquinotrion B.116 glyphosate B.117 glyphosate ammonium B.118 glyphosate-dimethylammonium B.119 isopropylammonium glyphosate B.120 glyphosate trimesium (sulfosate)

-20042660

B.121 glyphosate potassium B.122 glufosinate B.123 ammonium glufosinate B.124 glufosinate-R B.125 glufosinate-P-ammonium B.126 pendimethalin B.127 trifluralin B.128 acetochlor B.129 butachlor B.130 cafenstrol B.131 dimethenamid-R B.132 fentr azamide B.133 flufenacet B.134 mefenacet B.135 metazachlor B.136 metolachlor B.137 S-metolachlor B.138 pretilachlor B.139 phenoxasulfone B.140 indaziflam B.141 isoxaben B.142 triaziflam B.143 ipfencarbazon B.144 pyroxasulfone B.145 2,4-D B.146 2,4-B-isobutyl B.147 2,4-P-dimethylammonium B.148 2,4-D-N,N,N- trimethylethanolammonium B.149 aminopyralid B.150 aminopyralid-methyl B.151 aminopyralide-dimethylammonium B.152 aminopyralid-tris(2hydroxypropyl)ammonium B.153 clopyralid B.154 clopyralid-methyl B.155 clopyralid-olamine B.156 dicamba B.157 dicamba-butyl B.158 dicamba diglycolamine B.159 dicamba-dimethylammonium B.160 dicamba diolamine B.161 dicambaisopropylammonium B.162 dicamba-potassium B.163 dicamba sodium B.164 dicamba trolamine B.201 2-chloro-3-methylsulfanylN-(l-methyltetr azol-5-yl)4-(trifluoromethyl)benzamide (CAS 1361139-71-0)

B.165 dicamba-T4,M-bis-(3aminopropyl)methylamine B.166 dicamba-diethylenetriamine B.167 fluroxypyr B.168 fluroxypyr-meptyl B.169 galauxifen B.170 galauxifen-methyl B.171 MSRA B.172 MCPA-2-ethylhexyl B.173 MCPA-dimethylammonium B.174 quinclorac B.175 quincloracdimethylammonium B.176 quinmerak B.177 quinmeracdimethylammonium B.178 florpyrauxifen B.179 florpyrauxifen-benzyl (CAS 1390661-72-9) B.180 aminocyclopyrachlor B.181 aminocyclopyrachloropotassium B.182 aminocyclopyrachloromethyl B.183 diflufenzopyr B.184 diflufenzopyr sodium B.185 dimron B.186 indanophane B.187 oxacyclomefon B.188 II. 1 B.189 II.2 B.190 P.Z B.191 II.4 B.192 II.5 B.193 II.6 B.194 II.7 B.195 II.8 B.196 II.9 B.197 4-amino-3-chloro-5-fluoro-6(7-fluoro-1H-indol-6yl)picolinic acid (CAS 1629965-65-6) B.198 flopirauxifen B.199 oxotrione (CAS 148661721-3) B.200 cinmethylin

B.202 2-(2,4-dichlorophenyl)methyl- 4,4-Dimethyl-Zisoxazolidone (CAS 81777-95-9)

In addition, it may be useful to use the compounds of formula (I) in combination with safeners and, optionally, with one or more additional herbicides. Safeners are chemical compounds which prevent or reduce damage to beneficial plants without significantly affecting the herbicidal action of the compounds of formula (I) against undesirable plants. They can be applied either before sowing a useful plant (for example, when treating seeds, shoots or seedlings), or pre-emergence or post-emergence. Safeners and compounds of formula (I) and optionally herbicides B can be applied simultaneously or sequentially.

Suitable safeners are, for example, (quinoline-8-hydroxy)acetic acid, 1-phenyl5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5- alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazole carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[ [4(aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1,8-naphthalic anhydride, 2-halo-4(haloalkyl)-5-thiazolecarboxylic acids, phosphorothiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such as amides, esters and thioesters, provided that they have an acidic group.

Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cy-21 042660 prosulfamide, dichlormide, dicyclonone, dietholate, fenchlorazole, fenchlorim, flurazol, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabethrinyl, 4-(dichloroacetyl) 1oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3oxazolidine (R-29148, CAS 52836-31-4) and N-(2-methoxybenzoyl)-4[(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-12-0).

Particularly preferred safeners C are the following compounds C.1 - C.17 listed in table. WITH.

C.1 benoxacor C.3 cloquintocet-mexil C.5 dichlormide C.7 fenchlorazole-ethyl C.9 furilazole S.I isoxadifen-ethyl p.13 mefenpyr-diethyl p.15 4-(dichloroacetyl)-1-oxa-4azaspiro[4.5]decane p.17 N-(2-methoκcibenzoyl)-4[(methylaminocarbonyl)amino]benzenesulfonamide

Table C

C.2 cloquintocet C.4 cyprosulfamide C.6 fenchlorazole C.8 fenclorim p.10 isoxadifen p.12 mefenpyr p.14 naphthalic anhydride p.16 2,2,5-trimethyl-3(dichloroacetyl)-1,3 oxazolidine p.17 methcamifen

The active compounds B of groups b1)-b15) and the safener compounds C are known herbicides and safeners, see for example The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000, Volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th Edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, 7th edition supplement, Weed Science Society of America, 1998. 2,2,5-trimethyl-3(dichloroacetyl)-1,3-oxazolidine [CAS no. 52836-31-4], also referred to as R-29148. 4(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS no. 71526-07-3], also referred to as AD-67 and MON 4660.

The distribution of active compounds to their respective mechanisms of action is based on current knowledge. If multiple mechanisms of action apply to the same active compound, then the substance has been identified for only one mechanism of action.

The weight ratios of the individual components in the preferred mixtures mentioned below are within the ranges indicated above, in particular within the preferred ranges.

Particularly preferred are the following compositions containing a compound of formula (I) as defined above and a substance(s) as defined in the corresponding row of Table. 1;

particularly preferred compounds containing as herbicidal active compounds only, compounds I.a.A-1.1-I.a.A-1.192, I.b.A-2.1-I.b.A-2.192, I.c.A-3.1-I.c.A-3.192 as defined and substance(s) as defined in the corresponding row of Table 1.

- 22 042660

Table 1

conn. No. herbicide B safener C 1.1 IN 1 — 1.2 AT 2 — 1.3 v.z — 1.4 AT 4 — 1.5 AT 5 — 1.6 AT 6 — 1.7 AT 7 — 1.8 AT 8 — 1.9 AT 9 — 1.10 AT 10 — 1.11 in and — 1.12 AT 12 — 1.13 B.13 — 1.14 B.14 — 1.15 B.15 — 1.16 B.16 — 1.17 B.17 — 1.18 B.18 — 1.19 B.19 — 1.20 IN 20 — 1.21 AT 21 — 1.22 B.22 — 1.23 B.23 — 1.24 B.24 — 1.25 B.25 — 1.26 B.26 — 1.27 B.27 — 1.28 B.28 — 1.29 B.29 — 1.30 B.30 — 1.31 B.31 — 1.32 B.32 — 1.33 B.33 —

conn. No. herbicide B safener C 1.34 B.34 — 1.35 B.35 — 1.36 B.36 — 1.37 B.37 — 1.38 B.38 — 1.39 B.39 — 1.40 B.40 — 1.41 B.41 — 1.42 B.42 — 1.43 B.43 — 1.44 B.44 — 1.45 B.45 — 1.46 B.46 — 1.47 B.47 — 1.48 B.48 — 1.49 B.49 — 1.50 B.50 — 1.51 B.51 — 1.52 B.52 — 1.53 B.53 — 1.54 B.54 — 1.55 B.55 — 1.56 B.56 — 1.57 B.57 — 1.58 B.58. — 1.59 B.59 — 1.60 B.60 — 1.61 B.61 — 1.62 B.62 — 1.63 B.63 — 1.64 B.64 — 1.65 B.65 — 1.66 B.66 —

conn. No. herbicide B safener C 1.67 B.67 -- 1.68 B.68 -- 1.69 B.69 -- 1.70 B.70 -- 1.71 B.71 -- 1.72 B.72 -- 1.73 B.73 -- 1.74 B.74 -- 1.75 B.75 -- 1.76 B.76 -- 1.77 B.77 -- 1.78 B.78 -- 1.79 B.79 -- 1.80 B.80 -- 1.81 B.81 -- 1.82 B.82 -- 1.83 B.83 -- 1.84 B.84 -- 1.85 B.85 -- 1.86 B.86 -- 1.87 B.87 -- 1.88 B.88 -- 1.89 B.89 -- 1.90 B.90 -- 1.91 B.91 -- 1.92 B.92 -- 1.93 B.93 -- 1.94 B.94 -- 1.95 B.95 -- 1.96 B.96 -- 1.97 B.97 -- 1.98 B.98 -- 1.99 B.99 --

- 23 042660

1.100 B.100 — 1.101 B.101 — 1.102 B.102 — 1.103 B.103 — 1.104 B.104 — 1.105 B.105 — 1.106 B.106 — 1.107 B.107 — 1.108 B.108 — 1.109 B.109 — 1.110 B.110 — 1.111 B.111 — 1.112 B.112 — 1.113 V.IZ — 1.114 B.114 — 1.115 B.115 — 1.116 B.116 — 1.117 B.117 — 1.118 B.118 — 1.119 B.119 — 1.120 B.120 — 1.121 B.121 — 1.122 B.122 — 1.123 B.123 — 1.124 B.124 — 1.125 B.125 — 1.126 B.126 — 1.127 B.127 — 1.128 B.128 — 1.129 B.129 — 1.130 B.130 — 1.131 B.131 — 1.132 B.132 — 1.133 B.133 — 1.134 B.134 — 1.135 B.135 — 1.136 B.136 — 1.137 B.137 — 1.138 B.138 — 1.139 B.139 — 1.140 B.140 — 1.141 B.141 — 1.142 B.142 — 1.143 B.143 — 1.144 B.144 — 1.145 B.145 —

1.146 B.146 — 1.147 B.147 — 1.148 B.148 — 1.149 B.149 — 1.150 B.150 — 1.151 B.151 — 1.152 B.152 — 1.153 B.153 — 1.154 B.154 — 1.155 B.155 — 1.156 B.156 — 1.157 B.157 — 1.158 B.158 — 1.159 B.159 — 1.160 B.160 — 1.161 B.161 — 1.162 B.162 — 1.163 B.163 — 1.164 B.164 — 1.165 B.165 — 1.166 B.166 — 1.167 B.167 — 1.168 B.168 — 1.169 B.169 — 1.170 B.170 — 1.171 B.171 — 1.172 B.172 — 1.173 B.173 — 1.174 B.174 — 1.175 B.175 — 1.176 B.176 — 1.177 B.177 — 1.178 B.178 — 1.179 B.179 — 1.180 B.180 — 1.181 B.181 — 1.182 B.182 — 1.183 B.183 — 1.184 B.184 — 1.185 B.185 — 1.186 B.186 — 1.187 B.187 — 1.188 B.188 — 1.189 B.189 — 1.190 B.190 — 1.191 B.191 —

1.192 B.192 -- 1.193 B.193 -- 1.194 B.194 -- 1.195 B.195 -- 1.196 B.196 -- 1.197 B.197 -- 1.198 B.198 -- 1.199 B.199 -- 1.200 B.200 -- 1.201 B.201 -- 1.202 IN 1 C.1 1.203 AT 2 C.1 1.204 B.3 C.1 1.205 AT 4 C.1 1.206 AT 5 C.1 1.207 AT 6 C.1 1.208 AT 7 C.1 1.209 AT 8 C.1 1.210 AT 9 C.1 1.211 AT 10 C.1 1.212 in and C.1 1.213 AT 12 C.1 1.214 B.13 C.1 1.215 B.14 C.1 1.216 B.15 C.1 1.217 B.16 C.1 1.218 B.17 C.1 1.219 B.18 C.1 1.220 B.19 C.1 1.221 IN 20 C.1 1.222 AT 21 C.1 1.223 B.22 C.1 1.224 B.23 C.1 1.225 B.24 C.1 1.226 B.25 C.1 1.227 B.26 C.1 1.228 B.27 C.1 1.229 B.28 C.1 1.230 B.29 C.1 1.231 B.30 C.1 1.232 B.31 C.1 1.233 B.32 C.1 1.234 B.33 C.1 1.235 B.34 C.1 1.236 B.35 C.1 1.237 B.36 C.1

-24042660

1.238 B.37 C.1 1.239 B.38 C.1 1.240 B.39 C.1 1.241 B.40 C.1 1.242 B.41 C.1 1.243 B.42 C.1 1.244 VAZ C.1 1.245 B.44 C.1 1.246 B.45 C.1 1.247 B.46 C.1 1.248 B.47 C.1 1.249 B.48 C.1 1.250 B.49 C.1 1.251 B.50 C.1 1.252 B.51 C.1 1.253 B.52 C.1 1.254 B.53 C.1 1.255 B.54 C.1 1.256 B.55 C.1 1.257 B.56 C.1 1.258 B.57 C.1 1.259 B.58. C.1 1.260 B.59 C.1 1.261 B.60 C.1 1.262 B.61 C.1 1.263 B.62 C.1 1.264 B.63 C.1 1.265 B.64 C.1 1.266 B.65 C.1 1.267 B.66 C.1 1.268 B.67 C.1 1.269 B.68 C.1 1.270 B.69 C.1 1.271 B.70 C.1 1.272 B.71 C.1 1.273 B.72 C.1 1.274 B.73 C.1 1.275 B.74 C.1 1.276 B.75 C.1 1.277 B.76 C.1 1.278 B.77 C.1 1.279 B.78 C.1 1.280 B.79 C.1 1.281 B.80 C.1 1.282 B.81 C.1 1.283 B.82 C.1

1.284 B.83 C.1 1.285 B.84 C.1 1.286 B.85 C.1 1.287 B.86 C.1 1.288 B.87 C.1 1.289 B.88 C.1 1.290 B.89 C.1 1.291 B.90 C.1 1.292 B.91 C.1 1.293 B.92 C.1 1.294 B.93 C.1 1.295 B.94 C.1 1.296 B.95 C.1 1.297 B.96 C.1 1.298 B.97 C.1 1.299 B.98 C.1 1.300 B.99 C.1 1.301 B.100 C.1 1.302 B.101 C.1 1.303 B.102 C.1 1.304 B.103 C.1 1.305 B.104 C.1 1.306 B.105 C.1 1.307 B.106 C.1 1.308 B.107 C.1 1.309 B.108 C.1 1.310 B.109 C.1 1.311 B.110 C.1 1.312 B.111 C.1 1.313 B.112 C.1 1.314 B.113 C.1 1.315 B.114 C.1 1.316 B.115 C.1 1.317 B.116 C.1 1.318 B.117 C.1 1.319 B.118 C.1 1.320 B.119 C.1 1.321 B.120 C.1 1.322 B.121 C.1 1.323 B.122 C.1 1.324 B.123 C.1 1.325 B.124 C.1 1.326 B.125 C.1 1.327 B.126 C.1 1.328 B.127 C.1 1.329 B.128 C.1

1.330 B.129 C.1 1.331 B.130 C.1 1.332 B.131 C.1 1.333 B.132 C.1 1.334 B.133 C.1 1.335 B.134 C.1 1.336 B.135 C.1 1.337 B.136 C.1 1.338 B.137 C.1 1.339 B.138 C.1 1.340 B.139 C.1 1.341 B.140 C.1 1.342 B.141 C.1 1.343 B.142 C.1 1.344 B.143 C.1 1.345 B.144 C.1 1.346 B.145 C.1 1.347 B.146 C.1 1.348 B.147 C.1 1.349 B.148 C.1 1.350 B.149 C.1 1.351 B.150 C.1 1.352 B.151 C.1 1.353 B.152 C.1 1.354 B.153 C.1 1.355 B.154 C.1 1.356 B.155 C.1 1.357 B.156 C.1 1.358 B.157 C.1 1.359 B.158 C.1 1.360 B.159 C.1 1.361 B.160 C.1 1.362 B.161 C.1 1.363 B.162 C.1 1.364 B.163 C.1 1.365 B.164 C.1 1.366 B.165 C.1 1.367 B.166 C.1 1.368 B.167 C.1 1.369 B.168 C.1 1.370 B.169 C.1 1.371 B.170 C.1 1.372 B.171 C.1 1.373 B.172 C.1 1.374 B.173 C.1 1.375 B.174 C.1

- 25 042660

1.376 B.175 C.1 1.377 B.176 C.1 1.378 B.177 C.1 1.379 B.178 C.1 1.380 B.179 C.1 1.381 B.180 C.1 1.382 B.181 C.1 1.383 B.182 C.1 1.384 B.183 C.1 1.385 B.184 C.1 1.386 B.185 C.1 1.387 B.186 C.1 1.388 B.187 C.1 1.389 B.188 C.1 1.390 B.189 C.1 1.391 B.190 C.1 1.392 B.191 C.1 1.393 B.192 C.1 1.394 B.193 C.1 1.395 B.194 C.1 1.396 B.195 C.1 1.397 B.196 C.1 1.398 B.197 C.1 1.399 B.198 C.1 1.400 B.199 C.1 1.401 B.200 C.1 1.402 B.201 C.1 1.403 IN 1 C.2 1.404 AT 2 C.2 1.405 v.z C.2 1.406 AT 4 C.2 1.407 AT 5 C.2 1.408 AT 6 C.2 1.409 AT 7 C.2 1.410 AT 8 C.2 1.411 AT 9 C.2 1.412 AT 10 C.2 1.413 in and C.2 1.414 AT 12 C.2 1.415 B.13 C.2 1.416 B.14 C.2 1.417 B.15 C.2 1.418 B.16 C.2 1.419 B.17 C.2 1.420 B.18 C.2 1.421 B.19 C.2

1.422 IN 20 C.2 1.423 AT 21 C.2 1.424 B.22 C.2 1.425 B.23 C.2 1.426 B.24 C.2 1.427 B.25 C.2 1.428 B.26 C.2 1.429 B.27 C.2 1.430 B.28 C.2 1.431 B.29 C.2 1.432 B.30 C.2 1.433 B.31 C.2 1.434 B.32 C.2 1.435 B.33 C.2 1.436 B.34 C.2 1.437 B.35 C.2 1.438 B.36 C.2 1.439 B.37 C.2 1.440 B.38 C.2 1.441 B.39 C.2 1.442 B.40 C.2 1.443 B.41 C.2 1.444 B.42 C.2 1.445 B.43 C.2 1.446 B.44 C.2 1.447 B.45 C.2 1.448 B.46 C.2 1.449 B.47 C.2 1.450 B.48 C.2 1.451 B.49 C.2 1.452 B.50 From 2 1.453 B.51 C.2 1.454 B.52 C.2 1.455 B.53 C.2 1.456 B.54 C.2 1.457 B.55 C.2 1.458 B.56 C.2 1.459 B.57 C.2 1.460 B.58. C.2 1.461 B.59 C.2 1.462 B.60 C.2 1.463 B.61 C.2 1.464 B.62 C.2 1.465 B.63 C.2 1.466 B.64 C.2 1.467 B.65 C.2

1.468 B.66 C.2 1.469 B.67 C.2 1.470 B.68 C.2 1.471 B.69 C.2 1.472 B.70 C.2 1.473 B.71 C.2 1.474 B.72 C.2 1.475 B.73 C.2 1.476 B.74 C.2 1.477 B.75 C.2 1.478 B.76 C.2 1.479 B.77 C.2 1.480 B.78 C.2 1.481 B.79 C.2 1.482 B.80 C.2 1.483 B.81 C.2 1.484 B.82 C.2 1.485 B.83 C.2 1.486 B.84 C.2 1.487 B.85 C.2 1.488 B.86 C.2 1.489 B.87 C.2 1.490 B.88 C.2 1.491 B.89 C.2 1.492 B.90 C.2 1.493 B.91 C.2 1.494 B.92 C.2 1.495 B.93 C.2 1.496 B.94 C.2 1.497 B.95 C.2 1.498 B.96 C.2 1.499 B.97 C.2 1.500 B.98 C.2 1.501 B.99 C.2 1.502 B.100 C.2 1.503 B.101 C.2 1.504 B.102 C.2 1.505 B.103 C.2 1.506 B.104 C.2 1.507 B.105 C.2 1.508 B.106 C.2 1.509 B.107 C.2 1.510 B.108 C.2 1.511 B.109 C.2 1.512 B.110 C.2 1.513 B.111 C.2

- 26 042660

1.514 B.112 C.2 1.515 V.IZ C.2 1.516 B.114 C.2 1.517 B.115 C.2 1.518 B.116 C.2 1.519 B.117 C.2 1.520 B.118 C.2 1.521 B.119 C.2 1.522 B.120 C.2 1.523 B.121 C.2 1.524 B.122 C.2 1.525 B.123 C.2 1.526 B.124 C.2 1.527 B.125 C.2 1.528 B.126 C.2 1.529 B.127 C.2 1.530 B.128 C.2 1.531 B.129 C.2 1.532 B.130 C.2 1.533 B.131 C.2 1.534 B.132 C.2 1.535 B.133 C.2 1.536 B.134 C.2 1.537 B.135 C.2 1.538 B.136 C.2 1.539 B.137 C.2 1.540 B.138 C.2 1.541 B.139 C.2 1.542 B.140 C.2 1.543 B.141 C.2 1.544 B.142 C.2 1.545 B.143 C.2 1.546 B.144 C.2 1.547 B.145 C.2 1.548 B.146 C.2 1.549 B.147 C.2 1.550 B.148 C.2 1.551 B.149 C.2 1.552 B.150 C.2 1.553 B.151 C.2 1.554 B.152 C.2 1.555 B.153 C.2 1.556 B.154 C.2 1.557 B.155 C.2 1.558 B.156 C.2 1.559 B.157 C.2

1.560 B.158 C.2 1.561 B.159 C.2 1.562 B.160 C.2 1.563 B.161 C.2 1.564 B.162 C.2 1.565 B.163 C.2 1.566 B.164 C.2 1.567 B.165 C.2 1.568 B.166 C.2 1.569 B.167 C.2 1.570 B.168 C.2 1.571 B.169 C.2 1.572 B.170 C.2 1.573 B.171 C.2 1.574 B.172 C.2 1.575 B.173 C.2 1.576 B.174 C.2 1.577 B.175 C.2 1.578 B.176 C.2 1.579 B.177 C.2 1.580 B.178 C.2 1.581 B.179 C.2 1.582 B.180 C.2 1.583 B.181 C.2 1.584 B.182 C.2 1.585 B.183 C.2 1.586 B.184 C.2 1.587 B.185 C.2 1.588 B.186 C.2 1.589 B.187 C.2 1.590 B.188 C.2 1.591 B.189 C.2 1.592 B.190 C.2 1.593 B.191 C.2 1.594 B.192 C.2 1.595 B.193 C.2 1.596 B.194 C.2 1.597 B.195 C.2 1.598 B.196 C.2 1.599 B.197 C.2 1.600 B.198 C.2 1.601 B.199 C.2 1.602 B.200 C.2 1.603 B.201 C.2 1.604 IN 1 C.3 1.605 AT 2 C.3

1.606 v.z C.3 1.607 AT 4 C.3 1.608 AT 5 C.3 1.609 AT 6 C.3 1.610 AT 7 C.3 1.611 AT 8 C.3 1.612 AT 9 C.3 1.613 AT 10 C.3 1.614 in and C.3 1.615 AT 12 C.3 1.616 B.13 C.3 1.617 B.14 C.3 1.618 B.15 C.3 1.619 B.16 C.3 1.620 B.17 C.3 1.621 B.18 C.3 1.622 B.19 C.3 1.623 IN 20 C.3 1.624 AT 21 C.3 1.625 B.22 C.3 1.626 B.23 C.3 1.627 B.24 C.3 1.628 B.25 C.3 1.629 B.26 C.3 1.630 B.27 C.3 1.631 B.28 C.3 1.632 B.29 C.3 1.633 B.30 C.3 1.634 B.31 C.3 1.635 B.32 C.3 1.636 B.33 C.3 1.637 B.34 C.3 1.638 B.35 C.3 1.639 B.36 C.3 1.640 B.37 C.3 1.641 B.38 C.3 1.642 B.39 C.3 1.643 B.40 C.3 1.644 B.41 C.3 1.645 B.42 C.3 1.646 B.43 C.3 1.647 B.44 C.3 1.648 B.45 C.3 1.649 B.46 C.3 1.650 B.47 C.3 1.651 B.48 C.3

- 27 042660

1.652 B.49 C.3 1.653 B.50 C.3 1.654 B.51 C.3 1.655 B.52 C.3 1.656 B.53 C.3 1.657 B.54 C.3 1.658 B.55 C.3 1.659 B.56 C.3 1.660 B.57 C.3 1.661 B.58. C.3 1.662 B.59 C.3 1.663 B.60 C.3 1.664 B.61 C.3 1.665 B.62 C.3 1.666 B.63 C.3 1.667 B.64 C.3 1.668 B.65 C.3 1.669 B.66 C.3 1.670 B.67 C.3 1.671 B.68 C.3 1.672 B.69 C.3 1.673 B.70 C.3 1.674 B.71 C.3 1.675 B.72 C.3 1.676 B.73 C.3 1.677 B.74 C.3 1.678 B.75 C.3 1.679 B.76 C.3 1.680 B.77 C.3 1.681 B.78 C.3 1.682 B.79 C.3 1.683 B.80 C.3 1.684 B.81 C.3 1.685 B.82 C.3 1.686 B.83 C.3 1.687 B.84 C.3 1.688 B.85 C.3 1.689 B.86 C.3 1.690 B.87 C.3 1.691 B.88 C.3 1.692 B.89 C.3 1.693 B.90 C.3 1.694 B.91 C.3 1.695 B.92 C.3 1.696 B.93 C.3 1.697 B.94 C.3

1.698 B.95 C.3 1.699 B.96 C.3 1.700 B.97 C.3 1.701 B.98 C.3 1.702 B.99 C.3 1.703 B.100 C.3 1.704 B.101 C.3 1.705 B.102 C.3 1.706 B.103 C.3 1.707 B.104 C.3 1.708 B.105 C.3 1.709 B.106 C.3 1.710 B.107 C.3 1.711 B.108 C.3 1.712 B.109 C.3 1.713 V.PO C.3 1.714 Bill C.3 1.715 B.112 C.3 1.716 B.113 C.3 1.717 B.114 C.3 1.718 B.115 C.3 1.719 B.116 C.3 1.720 B.117 C.3 1.721 B.118 C.3 1.722 B.119 C.3 1.723 B.120 C.3 1.724 B.121 C.3 1.725 B.122 C.3 1.726 B.123 C.3 1.727 B.124 C.3 1.728 B.125 C.3 1.729 B.126 C.3 1.730 B.127 C.3 1.731 B.128 C.3 1.732 B.129 C.3 1.733 B.130 C.3 1.734 B.131 C.3 1.735 B.132 C.3 1.736 B.133 C.3 1.737 B.134 C.3 1.738 B.135 C.3 1.739 B.136 C.3 1.740 B.137 C.3 1.741 B.138 C.3 1.742 B.139 C.3 1.743 B.140 C.3

1.744 B.141 C.3 1.745 B.142 C.3 1.746 B.143 C.3 1.747 B.144 C.3 1.748 B.145 C.3 1.749 B.146 C.3 1.750 B.147 C.3 1.751 B.148 C.3 1.752 B.149 C.3 1.753 B.150 C.3 1.754 B.151 C.3 1.755 B.152 C.3 1.756 B.153 C.3 1.757 B.154 C.3 1.758 B.155 C.3 1.759 B.156 C.3 1.760 B.157 C.3 1.761 B.158 C.3 1.762 B.159 C.3 1.763 B.160 C.3 1.764 B.161 C.3 1.765 B.162 C.3 1.766 B.163 C.3 1.767 B.164 C.3 1.768 B.165 C.3 1.769 B.166 C.3 1.770 B.167 C.3 1.771 B.168 C.3 1.772 B.169 C.3 1.773 B.170 C.3 1.774 B.171 C.3 1.775 B.172 C.3 1.776 B.173 C.3 1.777 B.174 C.3 1.778 B.175 C.3 1.779 B.176 C.3 1.780 B.177 C.3 1.781 B.178 C.3 1.782 B.179 C.3 1.783 B.180 C.3 1.784 B.181 C.3 1.785 B.182 C.3 1.786 B.183 C.3 1.787 B.184 C.3 1.788 B.185 C.3 1.789 B.186 C.3

-28042660

1.790 B.187 s.z 1.791 B.188 s.z 1.792 B.189 s.z 1.793 B.190 s.z 1.794 B.191 s.z 1.795 B.192 s.z 1.796 B.193 s.z 1.797 B.194 s.z 1.798 B.195 s.z 1.799 B.196 s.z 1.800 B.197 s.z 1.801 B.198 s.z 1.802 B.199 s.z 1.803 B.200 s.z 1.804 B.201 s.z 1.805 IN 1 C.4 1.806 AT 2 C.4 1.807 v.z C.4 1.808 AT 4 C.4 1.809 AT 5 C.4 1.810 AT 6 C.4 1.811 AT 7 C.4 1.812 AT 8 C.4 1.813 AT 9 C.4 1.814 AT 10 C.4 1.815 in and C.4 1.816 AT 12 C.4 1.817 B.13 C.4 1.818 B.14 C.4 1.819 B.15 C.4 1.820 B.16 C.4 1.821 B.17 C.4 1.822 B.18 C.4 1.823 B.19 C.4 1.824 IN 20 C.4 1.825 AT 21 C.4 1.826 B.22 C.4 1.827 B.23 C.4 1.828 B.24 C.4 1.829 B.25 C.4 1.830 B.26 C.4 1.831 B.27 C.4 1.832 B.28 C.4 1.833 B.29 C.4 1.834 B.30 C.4 1.835 B.31 C.4

1.836 B.32 C.4 1.837 B.33 C.4 1.838 B.34 C.4 1.839 B.35 C.4 1.840 B.36 C.4 1.841 B.37 C.4 1.842 B.38 C.4 1.843 B.39 C.4 1.844 B.40 C.4 1.845 B.41 C.4 1.846 B.42 C.4 1.847 B.43 C.4 1.848 B.44 C.4 1.849 B.45 C.4 1.850 B.46 C.4 1.851 B.47 C.4 1.852 B.48 C.4 1.853 B.49 C.4 1.854 B.50 C.4 1.855 B.51 C.4 1.856 B.52 C.4 1.857 B.53 C.4 1.858 B.54 C.4 1.859 B.55 C.4 1.860 B.56 C.4 1.861 B.57 C.4 1.862 B.58. C.4 1.863 B.59 C.4 1.864 B.60 C.4 1.865 B.61 C.4 1.866 B.62 C.4 1.867 B.63 C.4 1.868 B.64 C.4 1.869 B.65 C.4 1.870 B.66 C.4 1.871 B.67 C.4 1.872 B.68 C.4 1.873 B.69 C.4 1.874 B.70 C.4 1.875 B.71 C.4 1.876 B.72 C.4 1.877 B.73 C.4 1.878 B.74 C.4 1.879 B.75 C.4 1.880 B.76 C.4 1.881 B.77 C.4

1.882 B.78 C.4 1.883 B.79 C.4 1.884 B.80 C.4 1.885 B.81 C.4 1.886 B.82 C.4 1.887 B.83 C.4 1.888 B.84 C.4 1.889 B.85 C.4 1.890 B.86 C.4 1.891 B.87 C.4 1.892 B.88 C.4 1.893 B.89 C.4 1.894 B.90 C.4 1.895 B.91 C.4 1.896 B.92 C.4 1.897 B.93 C.4 1.898 B.94 C.4 1.899 B.95 C.4 1.900 B.96 C.4 1.901 B.97 C.4 1.902 B.98 C.4 1.903 B.99 C.4 1.904 B.100 C.4 1.905 B.101 C.4 1.906 B.102 C.4 1.907 B.103 C.4 1.908 B.104 C.4 1.909 B.105 C.4 1.910 B.106 C.4 1.911 B.107 C.4 1.912 B.108 C.4 1.913 B.109 C.4 1.914 B.110 C.4 1.915 B.111 C.4 1.916 B.112 C.4 1.917 V.IZ C.4 1.918 B.114 C.4 1.919 B.115 C.4 1.920 B.116 C.4 1.921 B.117 C.4 1.922 B.118 C.4 1.923 B.119 C.4 1.924 B.120 C.4 1.925 B.121 C.4 1.926 B.122 C.4 1.927 B.123 C.4

- 29 042660

1.928 B.124 C.4 1.929 B.125 C.4 1.930 B.126 C.4 1.931 B.127 C.4 1.932 B.128 C.4 1.933 B.129 C.4 1.934 B.130 C.4 1.935 B.131 C.4 1.936 B.132 C.4 1.937 B.133 C.4 1.938 B.134 C.4 1.939 B.135 C.4 1.940 B.136 C.4 1.941 B.137 C.4 1.942 B.138 C.4 1.943 B.139 C.4 1.944 B.140 C.4 1.945 B.141 C.4 1.946 B.142 C.4 1.947 B.143 C.4 1.948 B.144 C.4 1.949 B.145 C.4 1.950 B.146 C.4 1.951 B.147 C.4 1.952 B.148 C.4 1.953 B.149 C.4 1.954 B.150 C.4 1.955 B.151 C.4 1.956 B.152 C.4 1.957 B.153 C.4 1.958 B.154 C.4 1.959 B.155 C.4 1.960 B.156 C.4 1.961 B.157 C.4 1.962 B.158 C.4 1.963 B.159 C.4 1.964 B.160 C.4 1.965 B.161 C.4 1.966 B.162 C.4 1.967 B.163 C.4 1.968 B.164 C.4 1.969 B.165 C.4 1.970 B.166 C.4 1.971 B.167 C.4 1.972 B.168 C.4 1.973 B.169 C.4

1.974 B.170 C.4 1.975 B.171 C.4 1.976 B.172 C.4 1.977 B.173 C.4 1.978 B.174 C.4 1.979 B.175 C.4 1.980 B.176 C.4 1.981 B.177 C.4 1.982 B.178 C.4 1.983 B.179 C.4 1.984 B.180 C.4 1.985 B.181 C.4 1.986 B.182 C.4 1.987 B.183 C.4 1.988 B.184 C.4 1.989 B.185 C.4 1.990 B.186 C.4 1.991 B.187 C.4 1.992 B.188 C.4 1.993 B.189 C.4 1.994 B.190 C.4 1.995 B.191 C.4 1.996 B.192 C.4 1.997 B.193 C.4 1.998 B.194 C.4 1.999 B.195 C.4 1.1000 B.196 C.4 1.1001 B.197 C.4 1.1002 B.198 C.4 1.1003 B.199 C.4 1.1004 B.200 C.4 1.1005 B.201 C.4 1.1006 IN 1 C.5 1.1007 AT 2 C.5 1.1008 B.3 C.5 1.1009 AT 4 C.5 1.1010 AT 5 C.5 1.1011 AT 6 C.5 1.1012 AT 7 C.5 1.1013 AT 8 C.5 1.1014 AT 9 C.5 1.1015 AT 10 C.5 1.1016 IN AND C.5 1.1017 AT 12 C.5 1.1018 B.13 C.5 1.1019 B.14 C.5

1.1020 B.15 C.5 1.1021 B.16 C.5 1.1022 B.17 C.5 1.1023 B.18 C.5 1.1024 B.19 C.5 1.1025 IN 20 C.5 1.1026 AT 21 C.5 1.1027 B.22 C.5 1.1028 B.23 C.5 1.1029 B.24 C.5 1.1030 B.25 C.5 1.1031 B.26 C.5 1.1032 B.27 C.5 1.1033 B.28 C.5 1.1034 B.29 C.5 1.1035 B.30 C.5 1.1036 B.31 C.5 1.1037 B.32 C.5 1.1038 B.33 C.5 1.1039 B.34 C.5 1.1040 B.35 C.5 1.1041 B.36 C.5 1.1042 B.37 C.5 1.1043 B.38 C.5 1.1044 B.39 C.5 1.1045 B.40 C.5 1.1046 B.41 C.5 1.1047 B.42 C.5 1.1048 B.43 C.5 1.1049 B.44 C.5 1.1050 B.45 From 5 1.1051 B.46 C.5 1.1052 B.47 C.5 1.1053 B.48 C.5 1.1054 B.49 C.5 1.1055 B.50 C.5 1.1056 B.51 C.5 1.1057 B.52 C.5 1.1058 B.53 C.5 1.1059 B.54 C.5 1.1060 B.55 C.5 1.1061 B.56 C.5 1.1062 B.57 C.5 1.1063 B.58. C.5 1.1064 B.59 C.5 1.1065 B.60 C.5

-30042660

1.1066 B.61 C.5 1.1067 B.62 C.5 1.1068 B.63 C.5 1.1069 B.64 C.5 1.1070 B.65 C.5 1.1071 B.66 C.5 1.1072 B.67 C.5 1.1073 B.68 C.5 1.1074 B.69 C.5 1.1075 B.70 C.5 1.1076 B.71 C.5 1.1077 B.72 C.5 1.1078 B.73 C.5 1.1079 B.74 C.5 1.1080 B.75 C.5 1.1081 B.76 C.5 1.1082 B.77 C.5 1.1083 B.78 C.5 1.1084 B.79 C.5 1.1085 B.80 C.5 1.1086 B.81 C.5 1.1087 B.82 C.5 1.1088 B.83 C.5 1.1089 B.84 C.5 1.1090 B.85 C.5 1.1091 B.86 C.5 1.1092 B.87 C.5 1.1093 B.88 C.5 1.1094 B.89 C.5 1.1095 B.90 C.5 1.1096 B.91 From 5 1.1097 B.92 C.5 1.1098 B.93 C.5 1.1099 B.94 C.5 1.1100 B.95 C.5 1.1101 B.96 C.5 1.1102 B.97 C.5 1.1103 B.98 C.5 1.1104 B.99 C.5 1.1105 B.100 C.5 1.1106 B.101 C.5 1.1107 B.102 C.5 1.1108 B.103 C.5 1.1109 B.104 C.5 1.1110 B.105 C.5 1.1111 B.106 C.5

1.1112 B.107 C.5 1.1113 B.108 C.5 1.1114 B.109 C.5 1.1115 B.110 C.5 1.1116 B.111 C.5 1.1117 B.112 C.5 1.1118 V.IZ C.5 1.1119 B.114 C.5 1.1120 B.115 C.5 1.1121 B.116 C.5 1.1122 B.117 C.5 1.1123 B.118 C.5 1.1124 B.119 C.5 1.1125 B.120 C.5 1.1126 B.121 C.5 1.1127 B.122 C.5 1.1128 B.123 C.5 1.1129 B.124 C.5 1.1130 B.125 C.5 1.1131 B.126 C.5 1.1132 B.127 C.5 1.1133 B.128 C.5 1.1134 B.129 C.5 1.1135 B.130 C.5 1.1136 B.131 C.5 1.1137 B.132 C.5 1.1138 B.133 C.5 1.1139 B.134 C.5 1.1140 B.135 C.5 1.1141 B.136 C.5 1.1142 B.137 From 5 1.1143 B.138 C.5 1.1144 B.139 C.5 1.1145 B.140 C.5 1.1146 B.141 C.5 1.1147 B.142 C.5 1.1148 B.143 C.5 1.1149 B.144 C.5 1.1150 B.145 C.5 1.1151 B.146 C.5 1.1152 B.147 C.5 1.1153 B.148 C.5 1.1154 B.149 C.5 1.1155 B.150 C.5 1.1156 B.151 C.5 1.1157 B.152 C.5

1.1158 B.153 C.5 1.1159 B.154 C.5 1.1160 B.155 C.5 1.1161 B.156 C.5 1.1162 B.157 C.5 1.1163 B.158 C.5 1.1164 B.159 C.5 1.1165 B.160 C.5 1.1166 B.161 C.5 1.1167 B.162 C.5 1.1168 B.163 C.5 1.1169 B.164 C.5 1.1170 B.165 C.5 1.1171 B.166 C.5 1.1172 B.167 C.5 1.1173 B.168 C.5 1.1174 B.169 C.5 1.1175 B.170 C.5 1.1176 B.171 C.5 1.1177 B.172 C.5 1.1178 B.173 C.5 1.1179 B.174 C.5 1.1180 B.175 C.5 1.1181 B.176 C.5 1.1182 B.177 C.5 1.1183 B.178 C.5 1.1184 B.179 C.5 1.1185 B.180 C.5 1.1186 B.181 C.5 1.1187 B.182 C.5 1.1188 B.183 From 5 1.1189 B.184 C.5 1.1190 B.185 C.5 1.1191 B.186 C.5 1.1192 B.187 C.5 1.1193 B.188 C.5 1.1194 B.189 C.5 1.1195 B.190 C.5 1.1196 B.191 C.5 1.1197 B.192 C.5 1.1198 B.193 C.5 1.1199 B.194 C.5 1.1200 B.195 C.5 1.1201 B.196 C.5 1.1202 B.197 C.5 1.1203 B.198 C.5

-31 042660

1.1204 B.199 C.5 1.1205 B.200 C.5 1.1206 B.201 C.5 1.1207 IN 1 C.6 1.1208 AT 2 C.6 1.1209 v.z C.6 1.1210 AT 4 C.6 1.1211 AT 5 C.6 1.1212 AT 6 C.6 1.1213 AT 7 C.6 1.1214 AT 8 C.6 1.1215 AT 9 C.6 1.1216 AT 10 C.6 1.1217 in and C.6 1.1218 AT 12 C.6 1.1219 B.13 C.6 1.1220 B.14 C.6 1.1221 B.15 C.6 1.1222 B.16 C.6 1.1223 B.17 C.6 1.1224 B.18 C.6 1.1225 B.19 C.6 1.1226 IN 20 C.6 1.1227 AT 21 C.6 1.1228 B.22 C.6 1.1229 B.23 C.6 1.1230 B.24 C.6 1.1231 B.25 C.6 1.1232 B.26 C.6 1.1233 B.27 C.6 1.1234 B.28 C.6 1.1235 B.29 C.6 1.1236 B.30 C.6 1.1237 B.31 C.6 1.1238 B.32 C.6 1.1239 B.33 C.6 1.1240 B.34 C.6 1.1241 B.35 C.6 1.1242 B.36 C.6 1.1243 B.37 C.6 1.1244 B.38 C.6 1.1245 B.39 C.6 1.1246 B.40 C.6 1.1247 B.41 C.6 1.1248 B.42 C.6 1.1249 B.43 C.6

1.1250 B.44 C.6 1.1251 B.45 C.6 1.1252 B.46 C.6 1.1253 B.47 C.6 1.1254 B.48 C.6 1.1255 B.49 C.6 1.1256 B.50 C.6 1.1257 B.51 C.6 1.1258 B.52 C.6 1.1259 B.53 C.6 1.1260 B.54 C.6 1.1261 B.55 C.6 1.1262 B.56 C.6 1.1263 B.57 C.6 1.1264 B.58. C.6 1.1265 B.59 C.6 1.1266 B.60 C.6 1.1267 B.61 C.6 1.1268 B.62 C.6 1.1269 B.63 C.6 1.1270 B.64 C.6 1.1271 B.65 C.6 1.1272 B.66 C.6 1.1273 B.67 C.6 1.1274 B.68 C.6 1.1275 B.69 C.6 1.1276 B.70 C.6 1.1277 B.71 C.6 1.1278 B.72 C.6 1.1279 B.73 C.6 1.1280 B.74 C.6 1.1281 B.75 C.6 1.1282 B.76 C.6 1.1283 B.77 C.6 1.1284 B.78 C.6 1.1285 B.79 C.6 1.1286 B.80 C.6 1.1287 B.81 C.6 1.1288 B.82 C.6 1.1289 B.83 C.6 1.1290 B.84 C.6 1.1291 B.85 C.6 1.1292 B.86 C.6 1.1293 B.87 C.6 1.1294 B.88 C.6 1.1295 B.89 C.6

1.1296 B.90 C.6 1.1297 B.91 C.6 1.1298 B.92 C.6 1.1299 B.93 C.6 1.1300 B.94 C.6 1.1301 B.95 C.6 1.1302 B.96 C.6 1.1303 B.97 C.6 1.1304 B.98 C.6 1.1305 B.99 C.6 1.1306 B.100 C.6 1.1307 B.101 C.6 1.1308 B.102 C.6 1.1309 B.103 C.6 1.1310 B.104 C.6 1.1311 B.105 C.6 1.1312 B.106 C.6 1.1313 B.107 C.6 1.1314 B.108 C.6 1.1315 B.109 C.6 1.1316 B.110 C.6 1.1317 B.111 C.6 1.1318 B.112 C.6 1.1319 V.IZ C.6 1.1320 B.114 C.6 1.1321 B.115 C.6 1.1322 B.116 C.6 1.1323 B.117 C.6 1.1324 B.118 C.6 1.1325 B.119 C.6 1.1326 B.120 C.6 1.1327 B.121 C.6 1.1328 B.122 C.6 1.1329 B.123 C.6 1.1330 B.124 C.6 1.1331 B.125 C.6 1.1332 B.126 C.6 1.1333 B.127 C.6 1.1334 B.128 C.6 1.1335 B.129 C.6 1.1336 B.130 C.6 1.1337 B.131 C.6 1.1338 B.132 C.6 1.1339 B.133 C.6 1.1340 B.134 C.6 1.1341 B.135 C.6

- 32 042660

1.1342 B.136 C.6 1.1343 B.137 C.6 1.1344 B.138 C.6 1.1345 B.139 C.6 1.1346 B.140 C.6 1.1347 B.141 C.6 1.1348 B.142 C.6 1.1349 B.143 C.6 1.1350 B.144 C.6 1.1351 B.145 C.6 1.1352 B.146 C.6 1.1353 B.147 C.6 1.1354 B.148 C.6 1.1355 B.149 C.6 1.1356 B.150 C.6 1.1357 B.151 C.6 1.1358 B.152 C.6 1.1359 B.153 C.6 1.1360 B.154 C.6 1.1361 B.155 C.6 1.1362 B.156 C.6 1.1363 B.157 C.6 1.1364 B.158 C.6 1.1365 B.159 C.6 1.1366 B.160 C.6 1.1367 B.161 C.6 1.1368 B.162 C.6 1.1369 B.163 C.6 1.1370 B.164 C.6 1.1371 B.165 C.6 1.1372 B.166 C.6 1.1373 B.167 C.6 1.1374 B.168 C.6 1.1375 B.169 C.6 1.1376 B.170 C.6 1.1377 B.171 C.6 1.1378 B.172 C.6 1.1379 B.173 C.6 1.1380 B.174 C.6 1.1381 B.175 C.6 1.1382 B.176 C.6 1.1383 B.177 C.6 1.1384 B.178 C.6 1.1385 B.179 C.6 1.1386 B.180 C.6 1.1387 B.181 C.6

1.1388 B.182 C.6 1.1389 B.183 C.6 1.1390 B.184 C.6 1.1391 B.185 C.6 1.1392 B.186 C.6 1.1393 B.187 C.6 1.1394 B.188 C.6 1.1395 B.189 C.6 1.1396 B.190 C.6 1.1397 B.191 C.6 1.1398 B.192 C.6 1.1399 B.193 C.6 1.1400 B.194 C.6 1.1401 B.195 C.6 1.1402 B.196 C.6 1.1403 B.197 C.6 1.1404 B.198 C.6 1.1405 B.199 C.6 1.1406 B.200 C.6 1.1407 B.201 C.6 1.1408 IN 1 C.7 1.1409 AT 2 C.7 1.1410 v.z C.7 1.1411 AT 4 C.7 1.1412 AT 5 C.7 1.1413 AT 6 C.7 1.1414 AT 7 C.7 1.1415 AT 8 C.7 1.1416 AT 9 C.7 1.1417 AT 10 C.7 1.1418 IN AND C.7 1.1419 AT 12 C.7 1.1420 B.13 C.7 1.1421 B.14 C.7 1.1422 B.15 C.7 1.1423 B.16 C.7 1.1424 B.17 C.7 1.1425 B.18 C.7 1.1426 B.19 C.7 1.1427 IN 20 C.7 1.1428 AT 21 C.7 1.1429 B.22 C.7 1.1430 B.23 C.7 1.1431 B.24 C.7 1.1432 B.25 C.7 1.1433 B.26 C.7

1.1434 B.27 C.7 1.1435 B.28 C.7 1.1436 B.29 C.7 1.1437 B.30 C.7 1.1438 B.31 C.7 1.1439 B.32 C.7 1.1440 B.33 C.7 1.1441 B.34 C.7 1.1442 B.35 C.7 1.1443 B.36 C.7 1.1444 B.37 C.7 1.1445 B.38 C.7 1.1446 B.39 C.7 1.1447 B.40 C.7 1.1448 B.41 C.7 1.1449 B.42 C.7 1.1450 B.43 C.7 1.1451 B.44 C.7 1.1452 B.45 C.7 1.1453 B.46 C.7 1.1454 B.47 C.7 1.1455 B.48 C.7 1.1456 B.49 C.7 1.1457 B.50 C.7 1.1458 B.51 C.7 1.1459 B.52 C.7 1.1460 B.53 C.7 1.1461 B.54 C.7 1.1462 B.55 C.7 1.1463 B.56 C.7 1.1464 B.57 C.7 1.1465 B.58. C.7 1.1466 B.59 C.7 1.1467 B.60 C.7 1.1468 B.61 C.7 1.1469 B.62 C.7 1.1470 B.63 C.7 1.1471 B.64 C.7 1.1472 B.65 C.7 1.1473 B.66 C.7 1.1474 B.67 C.7 1.1475 B.68 C.7 1.1476 B.69 C.7 1.1477 B.70 C.7 1.1478 B.71 C.7 1.1479 B.72 C.7

-33 042660

1.1480 B.73 C.7 1.1524 B.117 C.7 1.1568 B.161 C.7 1.1481 B.74 C.7 1.1525 B.118 C.7 1.1569 B.162 C.7 1.1482 B.75 C.7 1.1526 B.119 C.7 1.1570 B.163 C.7 1.1483 B.76 C.7 1.1527 B.120 C.7 1.1571 B.164 C.7 1.1484 B.77 C.7 1.1528 B.121 C.7 1.1572 B.165 C.7 1.1485 B.78 C.7 1.1529 B.122 C.7 1.1573 B.166 C.7 1.1486 B.79 C.7 1.1530 B.123 C.7 1.1574 B.167 C.7 1.1487 B.80 C.7 1.1531 B.124 C.7 1.1575 B.168 C.7 1.1488 B.81 C.7 1.1532 B.125 C.7 1.1576 B.169 C.7 1.1489 B.82 C.7 1.1533 B.126 C.7 1.1577 B.170 C.7 1.1490 B.83 C.7 1.1534 B.127 C.7 1.1578 B.171 C.7 1.1491 B.84 C.7 1.1535 B.128 C.7 1.1579 B.172 C.7 1.1492 B.85 C.7 1.1536 B.129 C.7 1.1580 B.173 C.7 1.1493 B.86 C.7 1.1537 B.130 C.7 1.1581 B.174 C.7 1.1494 B.87 C.7 1.1538 B.131 C.7 1.1582 B.175 C.7 1.1495 B.88 C.7 1.1539 B.132 C.7 1.1583 B.176 C.7 1.1496 B.89 C.7 1.1540 B.133 C.7 1.1584 B.177 C.7 1.1497 B.90 C.7 1.1541 B.134 C.7 1.1585 B.178 C.7 1.1498 B.91 C.7 1.1542 B.135 C.7 1.1586 B.179 C.7 1.1499 B.92 C.7 1.1543 B.136 C.7 1.1587 B.180 C.7 1.1500 B.93 C.7 1.1544 B.137 C.7 1.1588 B.181 C.7 1.1501 B.94 C.7 1.1545 B.138 C.7 1.1589 B.182 C.7 1.1502 B.95 C.7 1.1546 B.139 C.7 1.1590 B.183 C.7 1.1503 B.96 C.7 1.1547 B.140 C.7 1.1591 B.184 C.7 1.1504 B.97 C.7 1.1548 B.141 C.7 1.1592 B.185 C.7 1.1505 B.98 C.7 1.1549 B.142 C.7 1.1593 B.186 C.7 1.1506 B.99 C.7 1.1550 B.143 C.7 1.1594 B.187 C.7 1.1507 B.100 C.7 1.1551 B.144 C.7 1.1595 B.188 C.7 1.1508 B.101 C.7 1.1552 B.145 C.7 1.1596 B.189 C.7 1.1509 B.102 C.7 1.1553 B.146 C.7 1.1597 B.190 C.7 1.1510 B.103 C.7 1.1554 B.147 C.7 1.1598 B.191 C.7 1.1511 B.104 C.7 1.1555 B.148 C.7 1.1599 B.192 C.7 1.1512 B.105 C.7 1.1556 B.149 C.7 1.1600 B.193 C.7 1.1513 B.106 C.7 1.1557 B.150 C.7 1.1601 B.194 C.7 1.1514 B.107 C.7 1.1558 B.151 C.7 1.1602 B.195 C.7 1.1515 B.108 C.7 1.1559 B.152 C.7 1.1603 B.196 C.7 1.1516 B.109 C.7 1.1560 B.153 C.7 1.1604 B.197 C.7 1.1517 B.110 C.7 1.1561 B.154 C.7 1.1605 B.198 C.7 1.1518 B.111 C.7 1.1562 B.155 C.7 1.1606 B.199 C.7 1.1519 B.112 C.7 1.1563 B.156 C.7 1.1607 B.200 C.7 1.1520 V.IZ C.7 1.1564 B.157 C.7 1.1608 B.201 C.7 1.1521 B.114 C.7 1.1565 B.158 C.7 1.1522 B.115 C.7 1.1566 B.159 C.7 1.1523 B.116 C.7 1.1567 B.160 C.7 1 1.1609 |in 1 1 p.8 1 [ 1.1610 | AT 2 1 p.8 I G 1.1611 | v.z 1 p.8 I

- 34 042660

1.1612 AT 4 C.8 1.1660 B.52 C.8 1.1708 B.100 C.8 1.1613 AT 5 C.8 1.1661 B.53 C.8 1.1709 B.101 C.8 1.1614 AT 6 C.8 1.1662 B.54 C.8 1.1710 B.102 C.8 1.1615 AT 7 C.8 1.1663 B.55 C.8 1.1711 B.103 C.8 1.1616 AT 8 C.8 1.1664 B.56 C.8 1.1712 B.104 C.8 1.1617 AT 9 C.8 1.1665 B.57 C.8 1.1713 B.105 C.8 1.1618 AT 10 C.8 1.1666 B.58. C.8 1.1714 B.106 C.8 1.1619 in and C.8 1.1667 B.59 C.8 1.1715 B.107 C.8 1.1620 AT 12 C.8 1.1668 B.60 C.8 1.1716 B.108 C.8 1.1621 B.13 C.8 1.1669 B.61 C.8 1.1717 B.109 C.8 1.1622 B.14 C.8 1.1670 B.62 C.8 1.1718 V.PO C.8 1.1623 B.15 C.8 1.1671 B.63 C.8 1.1719 Bill C.8 1.1624 B.16 C.8 1.1672 B.64 C.8 1.1720 B.112 C.8 1.1625 B.17 C.8 1.1673 B.65 C.8 1.1721 B.113 C.8 1.1626 B.18 C.8 1.1674 B.66 C.8 1.1722 B.114 C.8 1.1627 B.19 C.8 1.1675 B.67 C.8 1.1723 B.115 C.8 1.1628 IN 20 C.8 1.1676 B.68 C.8 1.1724 B.116 C.8 1.1629 AT 21 C.8 1.1677 B.69 C.8 1.1725 B.117 C.8 1.1630 B.22 C.8 1.1678 B.70 C.8 1.1726 B.118 C.8 1.1631 B.23 C.8 1.1679 B.71 C.8 1.1727 B.119 C.8 1.1632 B.24 C.8 1.1680 B.72 C.8 1.1728 B.120 C.8 1.1633 B.25 C.8 1.1681 B.73 C.8 1.1729 B.121 C.8 1.1634 B.26 C.8 1.1682 B.74 C.8 1.1730 B.122 C.8 1.1635 B.27 C.8 1.1683 B.75 C.8 1.1731 B.123 C.8 1.1636 B.28 C.8 1.1684 B.76 C.8 1.1732 B.124 C.8 1.1637 B.29 C.8 1.1685 B.77 C.8 1.1733 B.125 C.8 1.1638 B.30 C.8 1.1686 B.78 C.8 1.1734 B.126 C.8 1.1639 B.31 C.8 1.1687 B.79 C.8 1.1735 B.127 C.8 1.1640 B.32 C.8 1.1688 B.80 C.8 1.1736 B.128 C.8 1.1641 B.33 C.8 1.1689 B.81 C.8 1.1737 B.129 C.8 1.1642 B.34 C.8 1.1690 B.82 C.8 1.1738 B.130 C.8 1.1643 B.35 C.8 1.1691 B.83 C.8 1.1739 B.131 C.8 1.1644 B.36 C.8 1.1692 B.84 C.8 1.1740 B.132 C.8 1.1645 B.37 C.8 1.1693 B.85 C.8 1.1741 B.133 C.8 1.1646 B.38 C.8 1.1694 B.86 C.8 1.1742 B.134 C.8 1.1647 B.39 C.8 1.1695 B.87 C.8 1.1743 B.135 C.8 1.1648 B.40 C.8 1.1696 B.88 C.8 1.1744 B.136 C.8 1.1649 B.41 C.8 1.1697 B.89 C.8 1.1745 B.137 C.8 1.1650 B.42 C.8 1.1698 B.90 C.8 1.1746 B.138 C.8 1.1651 B.43 C.8 1.1699 B.91 C.8 1.1747 B.139 C.8 1.1652 B.44 C.8 1.1700 B.92 C.8 1.1748 B.140 C.8 1.1653 B.45 C.8 1.1701 B.93 C.8 1.1749 B.141 C.8 1.1654 B.46 C.8 1.1702 B.94 C.8 1.1750 B.142 C.8 1.1655 B.47 C.8 1.1703 B.95 C.8 1.1751 B.143 C.8 1.1656 B.48 C.8 1.1704 B.96 C.8 1.1752 B.144 C.8 1.1657 B.49 C.8 1.1705 B.97 C.8 1.1753 B.145 C.8 1.1658 B.50 C.8 1.1706 B.98 C.8 1.1754 B.146 C.8 1.1659 B.51 C.8 1.1707 B.99 C.8 1.1755 B.147 C.8

- 35 042660

1.1756 B.148 C.8 1.1757 B.149 C.8 1.1758 B.150 C.8 1.1759 B.151 C.8 1.1760 B.152 C.8 1.1761 B.153 C.8 1.1762 B.154 C.8 1.1763 B.155 C.8 1.1764 B.156 C.8 1.1765 B.157 C.8 1.1766 B.158 C.8 1.1767 B.159 C.8 1.1768 B.160 C.8 1.1769 B.161 C.8 1.1770 B.162 C.8 1.1771 B.163 C.8 1.1772 B.164 C.8 1.1773 B.165 C.8

1.1774 B.166 C.8 1.1775 B.167 C.8 1.1776 B.168 C.8 1.1777 B.169 C.8 1.1778 B.170 C.8 1.1779 B.171 C.8 1.1780 B.172 C.8 1.1781 B.173 C.8 1.1782 B.174 C.8 1.1783 B.175 C.8 1.1784 B.176 C.8 1.1785 B.177 C.8 1.1786 B.178 C.8 1.1787 B.179 C.8 1.1788 B.180 C.8 1.1789 B.181 C.8 1.1790 B.182 C.8 1.1791 B.183 C.8

1.1792 B.184 C.8 1.1793 B.185 C.8 1.1794 B.186 C.8 1.1795 B.187 C.8 1.1796 B.188 C.8 1.1797 B.189 C.8 1.1798 B.190 C.8 1.1799 B.191 C.8 1.1800 B.192 C.8 1.1801 B.193 C.8 1.1802 B.194 C.8 1.1803 B.195 C.8 1.1804 B.196 C.8 1.1805 B.197 C.8 1.1806 B.198 C.8 1.1807 B.199 C.8 1.1808 B.200 C.8 1.1809 B.201 C.8

1.1810 IN 1 C.9 1.1811 AT 2 C.9 1.1812 v.z C.9 1.1813 AT 4 C.9 1.1814 AT 5 C.9 1.1815 AT 6 C.9 1.1816 AT 7 C.9 1.1817 AT 8 C.9 1.1818 AT 9 C.9 1.1819 AT 10 C.9 1.1820 in and C.9 1.1821 AT 12 C.9 1.1822 B.13 C.9 1.1823 B.14 C.9 1.1824 B.15 C.9 1.1825 B.16 C.9 1.1826 B.17 C.9 1.1827 B.18 C.9 1.1828 B.19 C.9 1.1829 IN 20 C.9 1.1830 AT 21 C.9 1.1831 B.22 C.9 1.1832 B.23 C.9 1.1833 B.24 C.9 1.1834 B.25 C.9 1.1835 B.26 C.9 1.1836 B.27 C.9

1.1837 B.28 C.9 1.1838 B.29 C.9 1.1839 B.30 C.9 1.1840 B.31 C.9 1.1841 B.32 C.9 1.1842 B.33 C.9 1.1843 B.34 C.9 1.1844 B.35 C.9 1.1845 B.36 C.9 1.1846 B.37 C.9 1.1847 B.38 C.9 1.1848 B.39 C.9 1.1849 B.40 C.9 1.1850 B.41 C.9 1.1851 B.42 C.9 1.1852 B.43 C.9 1.1853 B.44 C.9 1.1854 B.45 C.9 1.1855 B.46 C.9 1.1856 B.47 C.9 1.1857 B.48 C.9 1.1858 B.49 C.9 1.1859 B.50 C.9 1.1860 B.51 C.9 1.1861 B.52 C.9 1.1862 B.53 C.9 1.1863 B.54 C.9

1.1864 B.55 C.9 1.1865 B.56 C.9 1.1866 B.57 C.9 1.1867 B.58. C.9 1.1868 B.59 C.9 1.1869 B.60 C.9 1.1870 B.61 C.9 1.1871 B.62 C.9 1.1872 B.63 C.9 1.1873 B.64 C.9 1.1874 B.65 C.9 1.1875 B.66 C.9 1.1876 B.67 C.9 1.1877 B.68 C.9 1.1878 B.69 C.9 1.1879 B.70 C.9 1.1880 B.71 C.9 1.1881 B.72 C.9 1.1882 B.73 C.9 1.1883 B.74 C.9 1.1884 B.75 C.9 1.1885 B.76 C.9 1.1886 B.77 C.9 1.1887 B.78 C.9 1.1888 B.79 C.9 1.1889 B.80 C.9 1.1890 B.81 C.9

- 36 042660

1.1891 B.82 C.9 1.1932 B.123 C.9 1.1973 B.164 C.9 1.1892 B.83 C.9 1.1933 B.124 C.9 1.1974 B.165 C.9 1.1893 B.84 C.9 1.1934 B.125 C.9 1.1975 B.166 C.9 1.1894 B.85 C.9 1.1935 B.126 C.9 1.1976 B.167 C.9 1.1895 B.86 C.9 1.1936 B.127 C.9 1.1977 B.168 C.9 1.1896 B.87 C.9 1.1937 B.128 C.9 1.1978 B.169 C.9 1.1897 B.88 C.9 1.1938 B.129 C.9 1.1979 B.170 C.9 1.1898 B.89 C.9 1.1939 B.130 C.9 1.1980 B.171 C.9 1.1899 B.90 C.9 1.1940 B.131 C.9 1.1981 B.172 C.9 1.1900 B.91 C.9 1.1941 B.132 C.9 1.1982 B.173 C.9 1.1901 B.92 C.9 1.1942 B.133 C.9 1.1983 B.174 C.9 1.1902 B.93 C.9 1.1943 B.134 C.9 1.1984 B.175 C.9 1.1903 B.94 C.9 1.1944 B.135 C.9 1.1985 B.176 C.9 1.1904 B.95 C.9 1.1945 B.136 C.9 1.1986 B.177 C.9 1.1905 B.96 C.9 1.1946 B.137 C.9 1.1987 B.178 C.9 1.1906 B.97 C.9 1.1947 B.138 C.9 1.1988 B.179 C.9 1.1907 B.98 C.9 1.1948 B.139 C.9 1.1989 B.180 C.9 1.1908 B.99 C.9 1.1949 B.140 C.9 1.1990 B.181 C.9 1.1909 B.100 C.9 1.1950 B.141 C.9 1.1991 B.182 C.9 1.1910 B.101 C.9 1.1951 B.142 C.9 1.1992 B.183 C.9 1.1911 B.102 C.9 1.1952 B.143 C.9 1.1993 B.184 C.9 1.1912 B.103 C.9 1.1953 B.144 C.9 1.1994 B.185 C.9 1.1913 B.104 C.9 1.1954 B.145 C.9 1.1995 B.186 C.9 1.1914 B.105 C.9 1.1955 B.146 C.9 1.1996 B.187 C.9 1.1915 B.106 C.9 1.1956 B.147 C.9 1.1997 B.188 C.9 1.1916 B.107 C.9 1.1957 B.148 C.9 1.1998 B.189 C.9 1.1917 B.108 C.9 1.1958 B.149 C.9 1.1999 B.190 C.9 1.1918 B.109 C.9 1.1959 B.150 C.9 1.2000 B.191 C.9 1.1919 B.110 C.9 1.1960 B.151 C.9 1.2001 B.192 C.9 1.1920 B.111 C.9 1.1961 B.152 C.9 1.2002 B.193 C.9 1.1921 B.112 C.9 1.1962 B.153 C.9 1.2003 B.194 C.9 1.1922 V.IZ C.9 1.1963 B.154 C.9 1.2004 B.195 C.9 1.1923 B.114 C.9 1.1964 B.155 C.9 1.2005 B.196 C.9 1.1924 B.115 C.9 1.1965 B.156 C.9 1.2006 B.197 C.9 1.1925 B.116 C.9 1.1966 B.157 C.9 1.2007 B.198 C.9 1.1926 B.117 C.9 1.1967 B.158 C.9 1.2008 B.199 C.9 1.1927 B.118 C.9 1.1968 B.159 C.9 1.2009 B.200 C.9 1.1928 B.119 C.9 1.1969 B.160 C.9 1.2010 B.201 C.9 1.1929 B.120 C.9 1.1970 B.161 C.9 1.1930 B.121 C.9 1.1971 B.162 C.9 1.1931 B.122 C.9 1.1972 B.163 C.9 1.2011 IN 1 p.10 1.2015 AT 5 p.10 1.2019 AT 9 p.10 1.2012 AT 2 p.10 1.2016 AT 6 p.10 1.2020 AT 10 p.10 1.2013 v.z p.10 1.2017 AT 7 p.10 1.2021 IN AND p.10 1.2014 AT 4 p.10 1.2018 AT 8 p.10 1.2022 AT 12 p.10

- 37 042660

1.2023 B.13 p.10 1.2071 B.61 p.10 1.2119 B.109 p.10 1.2024 B.14 p.10 1.2072 B.62 p.10 1.2120 B.110 p.10 1.2025 B.15 p.10 1.2073 B.63 p.10 1.2121 B.111 p.10 1.2026 B.16 p.10 1.2074 B.64 p.10 1.2122 B.112 p.10 1.2027 B.17 p.10 1.2075 B.65 p.10 1.2123 V.IZ p.10 1.2028 B.18 p.10 1.2076 B.66 p.10 1.2124 B.114 p.10 1.2029 B.19 p.10 1.2077 B.67 p.10 1.2125 B.115 p.10 1.2030 IN 20 p.10 1.2078 B.68 p.10 1.2126 B.116 p.10 1.2031 AT 21 p.10 1.2079 B.69 p.10 1.2127 B.117 p.10 1.2032 B.22 p.10 1.2080 B.70 p.10 1.2128 B.118 p.10 1.2033 B.23 p.10 1.2081 B.71 p.10 1.2129 B.119 p.10 1.2034 B.24 p.10 1.2082 B.72 p.10 1.2130 B.120 p.10 1.2035 B.25 p.10 1.2083 B.73 p.10 1.2131 B.121 p.10 1.2036 B.26 p.10 1.2084 B.74 p.10 1.2132 B.122 p.10 1.2037 B.27 p.10 1.2085 B.75 p.10 1.2133 B.123 p.10 1.2038 B.28 p.10 1.2086 B.76 p.10 1.2134 B.124 p.10 1.2039 B.29 p.10 1.2087 B.77 p.10 1.2135 B.125 p.10 1.2040 B.30 p.10 1.2088 B.78 p.10 1.2136 B.126 p.10 1.2041 B.31 p.10 1.2089 B.79 p.10 1.2137 B.127 p.10 1.2042 B.32 p.10 1.2090 B.80 p.10 1.2138 B.128 p.10 1.2043 B.33 p.10 1.2091 B.81 p.10 1.2139 B.129 p.10 1.2044 B.34 p.10 1.2092 B.82 p.10 1.2140 B.130 p.10 1.2045 B.35 p.10 1.2093 B.83 p.10 1.2141 B.131 p.10 1.2046 B.36 p.10 1.2094 B.84 p.10 1.2142 B.132 p.10 1.2047 B.37 p.10 1.2095 B.85 p.10 1.2143 B.133 p.10 1.2048 B.38 p.10 1.2096 B.86 p.10 1.2144 B.134 p.10 1.2049 B.39 p.10 1.2097 B.87 p.10 1.2145 B.135 p.10 1.2050 B.40 p.10 1.2098 B.88 p.10 1.2146 B.136 p.10 1.2051 B.41 p.10 1.2099 B.89 p.10 1.2147 B.137 p.10 1.2052 B.42 p.10 1.2100 B.90 p.10 1.2148 B.138 p.10 1.2053 B.43 p.10 1.2101 B.91 p.10 1.2149 B.139 p.10 1.2054 B.44 p.10 1.2102 B.92 p.10 1.2150 B.140 p.10 1.2055 B.45 p.10 1.2103 B.93 p.10 1.2151 B.141 p.10 1.2056 B.46 p.10 1.2104 B.94 p.10 1.2152 B.142 p.10 1.2057 B.47 p.10 1.2105 B.95 p.10 1.2153 B.143 p.10 1.2058 B.48 p.10 1.2106 B.96 p.10 1.2154 B.144 p.10 1.2059 B.49 p.10 1.2107 B.97 p.10 1.2155 B.145 p.10 1.2060 B.50 p.10 1.2108 B.98 p.10 1.2156 B.146 p.10 1.2061 B.51 p.10 1.2109 B.99 p.10 1.2157 B.147 p.10 1.2062 B.52 p.10 1.2110 B.100 p.10 1.2158 B.148 p.10 1.2063 B.53 p.10 1.2111 B.101 p.10 1.2159 B.149 p.10 1.2064 B.54 p.10 1.2112 B.102 p.10 1.2160 B.150 p.10 1.2065 B.55 p.10 1.2113 B.103 p.10 1.2161 B.151 p.10 1.2066 B.56 p.10 1.2114 B.104 p.10 1.2162 B.152 p.10 1.2067 B.57 p.10 1.2115 B.105 p.10 1.2163 B.153 p.10 1.2068 B.58. p.10 1.2116 B.106 p.10 1.2164 B.154 p.10 1.2069 B.59 p.10 1.2117 B.107 p.10 1.2165 B.155 p.10 1.2070 B.60 p.10 1.2118 B.108 p.10 1.2166 B.156 p.10

- 38 042660

1.2167 B.157 p.10 1.2168 B.158 p.10 1.2169 B.159 p.10 1.2170 B.160 p.10 1.2171 B.161 p.10 1.2172 B.162 p.10 1.2173 B.163 p.10 1.2174 B.164 p.10 1.2175 B.165 p.10 1.2176 B.166 p.10 1.2177 B.167 p.10 1.2178 B.168 p.10 1.2179 B.169 p.10 1.2180 B.170 p.10 1.2181 B.171 p.10

1.2182 B.172 p.10 1.2183 B.173 p.10 1.2184 B.174 p.10 1.2185 B.175 p.10 1.2186 B.176 p.10 1.2187 B.177 p.10 1.2188 B.178 p.10 1.2189 B.179 p.10 1.2190 B.180 p.10 1.2191 B.181 p.10 1.2192 B.182 p.10 1.2193 B.183 p.10 1.2194 B.184 p.10 1.2195 B.185 p.10 1.2196 B.186 p.10

1.2197 B.187 p.10 1.2198 B.188 p.10 1.2199 B.189 p.10 1.2200 B.190 p.10 1.2201 B.191 p.10 1.2202 B.192 p.10 1.2203 B.193 p.10 1.2204 B.194 p.10 1.2205 B.195 p.10 1.2206 B.196 p.10 1.2207 B.197 p.10 1.2208 B.198 p.10 1.2209 B.199 p.10 1.2210 B.200 p.10 1.2211 B.201 p.10

1.2212 IN 1 S.I 1.2213 AT 2 S.I 1.2214 v.z S.I 1.2215 AT 4 S.I 1.2216 AT 5 S.I 1.2217 AT 6 S.I 1.2218 AT 7 S.I 1.2219 AT 8 S.I 1.2220 AT 9 S.I 1.2221 AT 10 s.i 1.2222 in and s.i 1.2223 AT 12 s.i 1.2224 B.13 s.i 1.2225 B.14 s.i 1.2226 B.15 s.i 1.2227 B.16 s.i 1.2228 B.17 s.i 1.2229 B.18 s.i 1.2230 B.19 s.i 1.2231 IN 20 s.i 1.2232 AT 21 s.i 1.2233 B.22 s.i 1.2234 B.23 s.i 1.2235 B.24 s.i 1.2236 B.25 s.i 1.2237 B.26 s.i 1.2238 B.27 s.i 1.2239 B.28 s.i 1.2240 B.29 s.i 1.2241 B.30 s.i

1.2242 B.31 S.I 1.2243 B.32 S.I 1.2244 B.33 S.I 1.2245 B.34 S.I 1.2246 B.35 S.I 1.2247 B.36 S.I 1.2248 B.37 S.I 1.2249 B.38 s.i 1.2250 B.39 s.i 1.2251 B.40 s.i 1.2252 B.41 s.i 1.2253 B.42 s.i 1.2254 B.43 s.i 1.2255 B.44 s.i 1.2256 B.45 s.i 1.2257 B.46 s.i 1.2258 B.47 s.i 1.2259 B.48 s.i 1.2260 B.49 s.i 1.2261 B.50 s.i 1.2262 B.51 s.i 1.2263 B.52 s.i 1.2264 B.53 s.i 1.2265 B.54 s.i 1.2266 B.55 s.i 1.2267 B.56 s.i 1.2268 B.57 s.i 1.2269 B.58. s.i 1.2270 B.59 s.i 1.2271 B.60 s.i

1.2272 B.61 S.I 1.2273 B.62 S.I 1.2274 B.63 S.I 1.2275 B.64 S.I 1.2276 B.65 S.I 1.2277 B.66 S.I 1.2278 B.67 S.I 1.2279 B.68 S.I 1.2280 B.69 S.I 1.2281 B.70 S.I 1.2282 B.71 S.I 1.2283 B.72 S.I 1.2284 B.73 s.i 1.2285 B.74 s.i 1.2286 B.75 s.i 1.2287 B.76 s.i 1.2288 B.77 s.i 1.2289 B.78 s.i 1.2290 B.79 s.i 1.2291 B.80 s.i 1.2292 B.81 s.i 1.2293 B.82 s.i 1.2294 B.83 s.i 1.2295 B.84 s.i 1.2296 B.85 s.i 1.2297 B.86 s.i 1.2298 B.87 s.i 1.2299 B.88 s.i 1.2300 B.89 s.i 1.2301 B.90 s.i

- 39 042660

1.2302 B.91 S.I 1.2340 B.129 S.I 1.2378 B.167 S.I 1.2303 B.92 s.i 1.2341 B.130 S.I 1.2379 B.168 s.i 1.2304 B.93 s.i 1.2342 B.131 S.I 1.2380 B.169 s.i 1.2305 B.94 s.i 1.2343 B.132 S.I 1.2381 B.170 s.i 1.2306 B.95 s.i 1.2344 B.133 S.I 1.2382 B.171 s.i 1.2307 B.96 s.i 1.2345 B.134 s.i 1.2383 B.172 s.i 1.2308 B.97 s.i 1.2346 B.135 s.i 1.2384 B.173 s.i 1.2309 B.98 s.i 1.2347 B.136 s.i 1.2385 B.174 s.i 1.2310 B.99 s.i 1.2348 B.137 s.i 1.2386 B.175 s.i 1.2311 B.100 s.i 1.2349 B.138 s.i 1.2387 B.176 s.i 1.2312 B.101 s.i 1.2350 B.139 s.i 1.2388 B.177 s.i 1.2313 B.102 s.i 1.2351 B.140 s.i 1.2389 B.178 s.i 1.2314 B.103 s.i 1.2352 B.141 s.i 1.2390 B.179 s.i 1.2315 B.104 s.i 1.2353 B.142 s.i 1.2391 B.180 s.i 1.2316 B.105 s.i 1.2354 B.143 s.i 1.2392 B.181 s.i 1.2317 B.106 s.i 1.2355 B.144 s.i 1.2393 B.182 s.i 1.2318 B.107 s.i 1.2356 B.145 s.i 1.2394 B.183 s.i 1.2319 B.108 s.i 1.2357 B.146 s.i 1.2395 B.184 s.i 1.2320 B.109 s.i 1.2358 B.147 s.i 1.2396 B.185 s.i 1.2321 B.110 s.i 1.2359 B.148 s.i 1.2397 B.186 s.i 1.2322 B.111 s.i 1.2360 B.149 s.i 1.2398 B.187 s.i 1.2323 B.112 s.i 1.2361 B.150 s.i 1.2399 B.188 s.i 1.2324 V.IZ s.i 1.2362 B.151 s.i 1.2400 B.189 s.i 1.2325 B.114 s.i 1.2363 B.152 s.i 1.2401 B.190 s.i 1.2326 B.115 s.i 1.2364 B.153 s.i 1.2402 B.191 s.i 1.2327 B.116 s.i 1.2365 B.154 s.i 1.2403 B.192 s.i 1.2328 B.117 s.i 1.2366 B.155 s.i 1.2404 B.193 s.i 1.2329 B.118 s.i 1.2367 B.156 s.i 1.2405 B.194 s.i 1.2330 B.119 s.i 1.2368 B.157 s.i 1.2406 B.195 s.i 1.2331 B.120 s.i 1.2369 B.158 s.i 1.2407 B.196 s.i 1.2332 B.121 s.i 1.2370 B.159 s.i 1.2408 B.197 s.i 1.2333 B.122 s.i 1.2371 B.160 s.i 1.2409 B.198 s.i 1.2334 B.123 s.i 1.2372 B.161 s.i 1.2410 B.199 s.i 1.2335 B.124 s.i 1.2373 B.162 s.i 1.2411 B.200 s.i 1.2336 B.125 s.i 1.2374 B.163 s.i 1.2412 B.201 s.i 1.2337 B.126 s.i 1.2375 B.164 s.i 1.2338 B.127 s.i 1.2376 B.165 s.i 1.2339 B.128 s.i 1.2377 B.166 s.i 1.2413 IN 1 p.12 1.2420 AT 8 p.12 1.2427 B.15 p.12 1.2414 AT 2 p.12 1.2421 AT 9 p.12 1.2428 B.16 p.12 1.2415 v.z p.12 1.2422 AT 10 p.12 1.2429 B.17 p.12 1.2416 AT 4 p.12 1.2423 IN AND p.12 1.2430 B.18 p.12 1.2417 AT 5 p.12 1.2424 AT 12 p.12 1.2431 B.19 p.12 1.2418 AT 6 p.12 1.2425 B.13 p.12 1.2432 IN 20 p.12 1.2419 AT 7 p.12 1.2426 B.14 p.12 1.2433 AT 21 p.12

- 40 042660

1.2434 B.22 p.12 1.2482 B.70 p.12 1.2530 B.118 p.12 1.2435 B.23 p.12 1.2483 B.71 p.12 1.2531 B.119 p.12 1.2436 B.24 p.12 1.2484 B.72 p.12 1.2532 B.120 p.12 1.2437 B.25 p.12 1.2485 B.73 p.12 1.2533 B.121 p.12 1.2438 B.26 p.12 1.2486 B.74 p.12 1.2534 B.122 p.12 1.2439 B.27 p.12 1.2487 B.75 p.12 1.2535 B.123 p.12 1.2440 B.28 p.12 1.2488 B.76 p.12 1.2536 B.124 p.12 1.2441 B.29 p.12 1.2489 B.77 p.12 1.2537 B.125 p.12 1.2442 B.30 p.12 1.2490 B.78 p.12 1.2538 B.126 p.12 1.2443 B.31 p.12 1.2491 B.79 p.12 1.2539 B.127 p.12 1.2444 B.32 p.12 1.2492 B.80 p.12 1.2540 B.128 p.12 1.2445 B.33 p.12 1.2493 B.81 p.12 1.2541 B.129 p.12 1.2446 B.34 p.12 1.2494 B.82 p.12 1.2542 B.130 p.12 1.2447 B.35 p.12 1.2495 B.83 p.12 1.2543 B.131 p.12 1.2448 B.36 p.12 1.2496 B.84 p.12 1.2544 B.132 p.12 1.2449 B.37 p.12 1.2497 B.85 p.12 1.2545 B.133 p.12 1.2450 B.38 p.12 1.2498 B.86 p.12 1.2546 B.134 p.12 1.2451 B.39 p.12 1.2499 B.87 p.12 1.2547 B.135 p.12 1.2452 B.40 p.12 1.2500 B.88 p.12 1.2548 B.136 p.12 1.2453 B.41 p.12 1.2501 B.89 p.12 1.2549 B.137 p.12 1.2454 B.42 p.12 1.2502 B.90 p.12 1.2550 B.138 p.12 1.2455 VAZ p.12 1.2503 B.91 p.12 1.2551 B.139 p.12 1.2456 B.44 p.12 1.2504 B.92 p.12 1.2552 B.140 p.12 1.2457 B.45 p.12 1.2505 B.93 p.12 1.2553 B.141 p.12 1.2458 B.46 p.12 1.2506 B.94 p.12 1.2554 B.142 p.12 1.2459 B.47 p.12 1.2507 B.95 p.12 1.2555 B.143 p.12 1.2460 B.48 p.12 1.2508 B.96 p.12 1.2556 B.144 p.12 1.2461 B.49 p.12 1.2509 B.97 p.12 1.2557 B.145 p.12 1.2462 B.50 p.12 1.2510 B.98 p.12 1.2558 B.146 p.12 1.2463 B.51 p.12 1.2511 B.99 p.12 1.2559 B.147 p.12 1.2464 B.52 p.12 1.2512 B.100 p.12 1.2560 B.148 p.12 1.2465 B.53 p.12 1.2513 B.101 p.12 1.2561 B.149 p.12 1.2466 B.54 p.12 1.2514 B.102 p.12 1.2562 B.150 p.12 1.2467 B.55 p.12 1.2515 B.103 p.12 1.2563 B.151 p.12 1.2468 B.56 p.12 1.2516 B.104 p.12 1.2564 B.152 p.12 1.2469 B.57 p.12 1.2517 B.105 p.12 1.2565 B.153 p.12 1.2470 B.58. p.12 1.2518 B.106 p.12 1.2566 B.154 p.12 1.2471 B.59 p.12 1.2519 B.107 p.12 1.2567 B.155 p.12 1.2472 B.60 p.12 1.2520 B.108 p.12 1.2568 B.156 p.12 1.2473 B.61 p.12 1.2521 B.109 p.12 1.2569 B.157 p.12 1.2474 B.62 p.12 1.2522 B.110 p.12 1.2570 B.158 p.12 1.2475 B.63 p.12 1.2523 B.111 p.12 1.2571 B.159 p.12 1.2476 B.64 p.12 1.2524 B.112 p.12 1.2572 B.160 p.12 1.2477 B.65 p.12 1.2525 V.IZ p.12 1.2573 B.161 p.12 1.2478 B.66 p.12 1.2526 B.114 p.12 1.2574 B.162 p.12 1.2479 B.67 p.12 1.2527 B.115 p.12 1.2575 B.163 p.12 1.2480 B.68 p.12 1.2528 B.116 p.12 1.2576 B.164 p.12 1.2481 B.69 p.12 1.2529 B.117 p.12 1.2577 B.165 p.12

- 41 042660

1.2578 B.166 p.12 1.2579 B.167 p.12 1.2580 B.168 p.12 1.2581 B.169 p.12 1.2582 B.170 p.12 1.2583 B.171 p.12 1.2584 B.172 p.12 1.2585 B.173 p.12 1.2586 B.174 p.12 1.2587 B.175 p.12 1.2588 B.176 p.12 1.2589 B.177 p.12

1.2590 B.178 p.12 1.2591 B.179 p.12 1.2592 B.180 p.12 1.2593 B.181 p.12 1.2594 B.182 p.12 1.2595 B.183 p.12 1.2596 B.184 p.12 1.2597 B.185 p.12 1.2598 B.186 p.12 1.2599 B.187 p.12 1.2600 B.188 p.12 1.2601 B.189 p.12

1.2602 B.190 p.12 1.2603 B.191 p.12 1.2604 B.192 p.12 1.2605 B.193 p.12 1.2606 B.194 p.12 1.2607 B.195 p.12 1.2608 B.196 p.12 1.2609 B.197 p.12 1.2610 B.198 p.12 1.2611 B.199 p.12 1.2612 B.200 p.12 1.2613 B.201 p.12

1.2614 IN 1 p.13 1.2615 AT 2 p.13 1.2616 v.z p.13 1.2617 AT 4 p.13 1.2618 AT 5 p.13 1.2619 AT 6 p.13 1.2620 AT 7 p.13 1.2621 AT 8 p.13 1.2622 AT 9 p.13 1.2623 AT 10 p.13 1.2624 in and p.13 1.2625 AT 12 p.13 1.2626 B.13 p.13 1.2627 B.14 p.13 1.2628 B.15 p.13 1.2629 B.16 p.13 1.2630 B.17 p.13 1.2631 B.18 p.13 1.2632 B.19 p.13 1.2633 IN 20 p.13 1.2634 AT 21 p.13 1.2635 B.22 p.13 1.2636 B.23 p.13 1.2637 B.24 p.13 1.2638 B.25 p.13 1.2639 B.26 p.13 1.2640 B.27 p.13 1.2641 B.28 p.13 1.2642 B.29 p.13 1.2643 B.30 p.13 1.2644 B.31 p.13 1.2645 B.32 p.13

1.2646 B.33 p.13 1.2647 B.34 p.13 1.2648 B.35 p.13 1.2649 B.36 p.13 1.2650 B.37 p.13 1.2651 B.38 p.13 1.2652 B.39 p.13 1.2653 B.40 p.13 1.2654 B.41 p.13 1.2655 B.42 p.13 1.2656 B.43 p.13 1.2657 B.44 p.13 1.2658 B.45 p.13 1.2659 B.46 p.13 1.2660 B.47 p.13 1.2661 B.48 p.13 1.2662 B.49 p.13 1.2663 B.50 p.13 1.2664 B.51 p.13 1.2665 B.52 p.13 1.2666 B.53 p.13 1.2667 B.54 p.13 1.2668 B.55 p.13 1.2669 B.56 p.13 1.2670 B.57 p.13 1.2671 B.58. p.13 1.2672 B.59 p.13 1.2673 B.60 p.13 1.2674 B.61 p.13 1.2675 B.62 p.13 1.2676 B.63 p.13 1.2677 B.64 p.13

1.2678 B.65 p.13 1.2679 B.66 p.13 1.2680 B.67 p.13 1.2681 B.68 p.13 1.2682 B.69 p.13 1.2683 B.70 p.13 1.2684 B.71 p.13 1.2685 B.72 p.13 1.2686 B.73 p.13 1.2687 B.74 p.13 1.2688 B.75 p.13 1.2689 B.76 p.13 1.2690 B.77 p.13 1.2691 B.78 p.13 1.2692 B.79 p.13 1.2693 B.80 p.13 1.2694 B.81 p.13 1.2695 B.82 p.13 1.2696 B.83 p.13 1.2697 B.84 p.13 1.2698 B.85 p.13 1.2699 B.86 p.13 1.2700 B.87 p.13 1.2701 B.88 p.13 1.2702 B.89 p.13 1.2703 B.90 p.13 1.2704 B.91 p.13 1.2705 B.92 p.13 1.2706 B.93 p.13 1.2707 B.94 p.13 1.2708 B.95 p.13 1.2709 B.96 p.13

- 42 042660

1.2710 B.97 p.13 1.2711 B.98 p.13 1.2712 B.99 p.13 1.2713 B.100 p.13 1.2714 B.101 p.13 1.2715 B.102 p.13 1.2716 B.103 p.13 1.2717 B.104 p.13 1.2718 B.105 p.13 1.2719 B.106 p.13 1.2720 B.107 p.13 1.2721 B.108 p.13 1.2722 B.109 p.13 1.2723 B.110 p.13 1.2724 B.111 p.13 1.2725 B.112 p.13 1.2726 V.IZ p.13 1.2727 B.114 p.13 1.2728 B.115 p.13 1.2729 B.116 p.13 1.2730 B.117 p.13 1.2731 B.118 p.13 1.2732 B.119 p.13 1.2733 B.120 p.13 1.2734 B.121 p.13 1.2735 B.122 p.13 1.2736 B.123 p.13 1.2737 B.124 p.13 1.2738 B.125 p.13 1.2739 B.126 p.13 1.2740 B.127 p.13 1.2741 B.128 p.13 1.2742 B.129 p.13 1.2743 B.130 p.13 1.2744 B.131 p.13 1.2745 B.132 p.13

1.2746 B.133 p.13 1.2747 B.134 p.13 1.2748 B.135 p.13 1.2749 B.136 p.13 1.2750 B.137 p.13 1.2751 B.138 p.13 1.2752 B.139 p.13 1.2753 B.140 p.13 1.2754 B.141 p.13 1.2755 B.142 p.13 1.2756 B.143 p.13 1.2757 B.144 p.13 1.2758 B.145 p.13 1.2759 B.146 p.13 1.2760 B.147 p.13 1.2761 B.148 p.13 1.2762 B.149 p.13 1.2763 B.150 p.13 1.2764 B.151 p.13 1.2765 B.152 p.13 1.2766 B.153 p.13 1.2767 B.154 p.13 1.2768 B.155 p.13 1.2769 B.156 p.13 1.2770 B.157 p.13 1.2771 B.158 p.13 1.2772 B.159 p.13 1.2773 B.160 p.13 1.2774 B.161 p.13 1.2775 B.162 p.13 1.2776 B.163 p.13 1.2777 B.164 p.13 1.2778 B.165 p.13 1.2779 B.166 p.13 1.2780 B.167 p.13 1.2781 B.168 p.13

1.2782 B.169 p.13 1.2783 B.170 p.13 1.2784 B.171 p.13 1.2785 B.172 p.13 1.2786 B.173 p.13 1.2787 B.174 p.13 1.2788 B.175 p.13 1.2789 B.176 p.13 1.2790 B.177 p.13 1.2791 B.178 p.13 1.2792 B.179 p.13 1.2793 B.180 p.13 1.2794 B.181 p.13 1.2795 B.182 p.13 1.2796 B.183 p.13 1.2797 B.184 p.13 1.2798 B.185 p.13 1.2799 B.186 p.13 1.2800 B.187 p.13 1.2801 B.188 p.13 1.2802 B.189 p.13 1.2803 B.190 p.13 1.2804 B.191 p.13 1.2805 B.192 p.13 1.2806 B.193 p.13 1.2807 B.194 p.13 1.2808 B.195 p.13 1.2809 B.196 p.13 1.2810 B.197 p.13 1.2811 B.198 p.13 1.2812 B.199 p.13 1.2813 B.200 p.13 1.2814 B.201 p.13

1.2815 IN 1 p.14 1.2816 AT 2 p.14 1.2817 v.z p.14 1.2818 AT 4 p.14 1.2819 AT 5 p.14 1.2820 AT 6 p.14 1.2821 AT 7 p.14 1.2822 AT 8 p.14 1.2823 AT 9 p.14

1.2824 AT 10 p.14 1.2825 IN AND p.14 1.2826 AT 12 p.14 1.2827 B.13 p.14 1.2828 B.14 p.14 1.2829 B.15 p.14 1.2830 B.16 p.14 1.2831 B.17 p.14 1.2832 B.18 p.14

1.2833 B.19 p.14 1.2834 IN 20 p.14 1.2835 AT 21 p.14 1.2836 B.22 p.14 1.2837 B.23 p.14 1.2838 B.24 p.14 1.2839 B.25 p.14 1.2840 B.26 p.14 1.2841 B.27 p.14

- 43 042660

1.2842 B.28 p.14 1.2843 B.29 p.14 1.2844 B.30 p.14 1.2845 B.31 p.14 1.2846 B.32 p.14 1.2847 B.33 p.14 1.2848 B.34 p.14 1.2849 B.35 p.14 1.2850 B.36 p.14 1.2851 B.37 p.14 1.2852 B.38 p.14 1.2853 B.39 p.14 1.2854 B.40 p.14 1.2855 B.41 p.14 1.2856 B.42 p.14 1.2857 B.43 p.14 1.2858 B.44 p.14 1.2859 B.45 p.14 1.2860 B.46 p.14 1.2861 B.47 p.14 1.2862 B.48 p.14 1.2863 B.49 p.14 1.2864 B.50 p.14 1.2865 B.51 p.14 1.2866 B.52 p.14 1.2867 B.53 p.14 1.2868 B.54 p.14 1.2869 B.55 p.14 1.2870 B.56 p.14 1.2871 B.57 p.14 1.2872 B.58. p.14 1.2873 B.59 p.14 1.2874 B.60 p.14 1.2875 B.61 p.14 1.2876 B.62 p.14 1.2877 B.63 p.14 1.2878 B.64 p.14 1.2879 B.65 p.14 1.2880 B.66 p.14 1.2881 B.67 p.14 1.2882 B.68 p.14 1.2883 B.69 p.14 1.2884 B.70 p.14 1.2885 B.71 p.14 1.2886 B.72 p.14 1.2887 B.73 p.14 1.2888 B.74 p.14 1.2889 B.75 p.14

1.2890 B.76 p.14 1.2891 B.77 p.14 1.2892 B.78 p.14 1.2893 B.79 p.14 1.2894 B.80 p.14 1.2895 B.81 p.14 1.2896 B.82 p.14 1.2897 B.83 p.14 1.2898 B.84 p.14 1.2899 B.85 p.14 1.2900 B.86 p.14 1.2901 B.87 p.14 1.2902 B.88 p.14 1.2903 B.89 p.14 1.2904 B.90 p.14 1.2905 B.91 p.14 1.2906 B.92 p.14 1.2907 B.93 p.14 1.2908 B.94 p.14 1.2909 B.95 p.14 1.2910 B.96 p.14 1.2911 B.97 p.14 1.2912 B.98 p.14 1.2913 B.99 p.14 1.2914 B.100 p.14 1.2915 B.101 p.14 1.2916 B.102 p.14 1.2917 B.103 p.14 1.2918 B.104 p.14 1.2919 B.105 p.14 1.2920 B.106 p.14 1.2921 B.107 p.14 1.2922 B.108 p.14 1.2923 B.109 p.14 1.2924 B.110 p.14 1.2925 Bill p.14 1.2926 B.112 p.14 1.2927 B.113 p.14 1.2928 B.114 p.14 1.2929 B.115 p.14 1.2930 B.116 p.14 1.2931 B.117 p.14 1.2932 B.118 p.14 1.2933 B.119 p.14 1.2934 B.120 p.14 1.2935 B.121 p.14 1.2936 B.122 p.14 1.2937 B.123 p.14

1.2938 B.124 p.14 1.2939 B.125 p.14 1.2940 B.126 p.14 1.2941 B.127 p.14 1.2942 B.128 p.14 1.2943 B.129 p.14 1.2944 B.130 p.14 1.2945 B.131 p.14 1.2946 B.132 p.14 1.2947 B.133 p.14 1.2948 B.134 p.14 1.2949 B.135 p.14 1.2950 B.136 p.14 1.2951 B.137 p.14 1.2952 B.138 p.14 1.2953 B.139 p.14 1.2954 B.140 p.14 1.2955 B.141 p.14 1.2956 B.142 p.14 1.2957 B.143 p.14 1.2958 B.144 p.14 1.2959 B.145 p.14 1.2960 B.146 p.14 1.2961 B.147 p.14 1.2962 B.148 p.14 1.2963 B.149 p.14 1.2964 B.150 p.14 1.2965 B.151 p.14 1.2966 B.152 p.14 1.2967 B.153 p.14 1.2968 B.154 p.14 1.2969 B.155 p.14 1.2970 B.156 p.14 1.2971 B.157 p.14 1.2972 B.158 p.14 1.2973 B.159 p.14 1.2974 B.160 p.14 1.2975 B.161 p.14 1.2976 B.162 p.14 1.2977 B.163 p.14 1.2978 B.164 p.14 1.2979 B.165 p.14 1.2980 B.166 p.14 1.2981 B.167 p.14 1.2982 B.168 p.14 1.2983 B.169 p.14 1.2984 B.170 p.14 1.2985 B.171 p.14

- 44 042660

1.2986 B.172 p.14 1.2987 B.173 p.14 1.2988 B.174 p.14 1.2989 B.175 p.14 1.2990 B.176 p.14 1.2991 B.177 p.14 1.2992 B.178 p.14 1.2993 B.179 p.14 1.2994 B.180 p.14 1.2995 B.181 p.14

1.2996 B.182 p.14 1.2997 B.183 p.14 1.2998 B.184 p.14 1.2999 B.185 p.14 1.3000 B.186 p.14 1.3001 B.187 p.14 1.3002 B.188 p.14 1.3003 B.189 p.14 1.3004 B.190 p.14 1.3005 B.191 p.14

1.3006 B.192 p.14 1.3007 B.193 p.14 1.3008 B.194 p.14 1.3009 B.195 p.14 1.3010 B.196 p.14 1.3011 B.197 p.14 1.3012 B.198 p.14 1.3013 B.199 p.14 1.3014 B.200 p.14 1.3015 B.201 p.14

1.3016 IN 1 p.15 1.3017 AT 2 p.15 1.3018 v.z p.15 1.3019 AT 4 p.15 1.3020 AT 5 p.15 1.3021 AT 6 p.15 1.3022 AT 7 p.15 1.3023 AT 8 p.15 1.3024 AT 9 p.15 1.3025 AT 10 p.15 1.3026 in and p.15 1.3027 AT 12 p.15 1.3028 B.13 p.15 1.3029 B.14 p.15 1.3030 B.15 p.15 1.3031 B.16 p.15 1.3032 B.17 p.15 1.3033 B.18 p.15 1.3034 B.19 p.15 1.3035 IN 20 p.15 1.3036 AT 21 p.15 1.3037 B.22 p.15 1.3038 B.23 p.15 1.3039 B.24 p.15 1.3040 B.25 p.15 1.3041 B.26 p.15 1.3042 B.27 p.15 1.3043 B.28 p.15 1.3044 B.29 p.15 1.3045 B.30 p.15 1.3046 B.31 p.15 1.3047 B.32 p.15 1.3048 B.33 p.15 1.3049 B.34 p.15 1.3050 B.35 p.15

1.3051 B.36 p.15 1.3052 B.37 p.15 1.3053 B.38 p.15 1.3054 B.39 p.15 1.3055 B.40 p.15 1.3056 B.41 p.15 1.3057 B.42 p.15 1.3058 B.43 p.15 1.3059 B.44 p.15 1.3060 B.45 p.15 1.3061 B.46 p.15 1.3062 B.47 p.15 1.3063 B.48 p.15 1.3064 B.49 p.15 1.3065 B.50 p.15 1.3066 B.51 p.15 1.3067 B.52 p.15 1.3068 B.53 p.15 1.3069 B.54 p.15 1.3070 B.55 p.15 1.3071 B.56 p.15 1.3072 B.57 p.15 1.3073 B.58. p.15 1.3074 B.59 p.15 1.3075 B.60 p.15 1.3076 B.61 p.15 1.3077 B.62 p.15 1.3078 B.63 p.15 1.3079 B.64 p.15 1.3080 B.65 p.15 1.3081 B.66 p.15 1.3082 B.67 p.15 1.3083 B.68 p.15 1.3084 B.69 p.15 1.3085 B.70 p.15

1.3086 B.71 p.15 1.3087 B.72 p.15 1.3088 B.73 p.15 1.3089 B.74 p.15 1.3090 B.75 p.15 1.3091 B.76 p.15 1.3092 B.77 p.15 1.3093 B.78 p.15 1.3094 B.79 p.15 1.3095 B.80 p.15 1.3096 B.81 p.15 1.3097 B.82 p.15 1.3098 B.83 p.15 1.3099 B.84 p.15 1.3100 B.85 p.15 1.3101 B.86 p.15 1.3102 B.87 p.15 1.3103 B.88 p.15 1.3104 B.89 p.15 1.3105 B.90 p.15 1.3106 B.91 p.15 1.3107 B.92 p.15 1.3108 B.93 p.15 1.3109 B.94 p.15 1.3110 B.95 p.15 1.3111 B.96 p.15 1.3112 B.97 p.15 1.3113 B.98 p.15 1.3114 B.99 p.15 1.3115 B.100 p.15 1.3116 B.101 p.15 1.3117 B.102 p.15 1.3118 B.103 p.15 1.3119 B.104 p.15 1.3120 B.105 p.15

- 45 042660

1.3121 B.106 p.15 1.3122 B.107 p.15 1.3123 B.108 p.15 1.3124 B.109 p.15 1.3125 B.110 p.15 1.3126 B.111 p.15 1.3127 B.112 p.15 1.3128 V.IZ p.15 1.3129 B.114 p.15 1.3130 B.115 p.15 1.3131 B.116 p.15 1.3132 B.117 p.15 1.3133 B.118 p.15 1.3134 B.119 p.15 1.3135 B.120 p.15 1.3136 B.121 p.15 1.3137 B.122 p.15 1.3138 B.123 p.15 1.3139 B.124 p.15 1.3140 B.125 p.15 1.3141 B.126 p.15 1.3142 B.127 p.15 1.3143 B.128 p.15 1.3144 B.129 p.15 1.3145 B.130 p.15 1.3146 B.131 p.15 1.3147 B.132 p.15 1.3148 B.133 p.15 1.3149 B.134 p.15 1.3150 B.135 p.15 1.3151 B.136 p.15 1.3152 B.137 p.15 1.3153 B.138 p.15

1.3154 B.139 p.15 1.3155 B.140 p.15 1.3156 B.141 p.15 1.3157 B.142 p.15 1.3158 B.143 p.15 1.3159 B.144 p.15 1.3160 B.145 p.15 1.3161 B.146 p.15 1.3162 B.147 p.15 1.3163 B.148 p.15 1.3164 B.149 p.15 1.3165 B.150 p.15 1.3166 B.151 p.15 1.3167 B.152 p.15 1.3168 B.153 p.15 1.3169 B.154 p.15 1.3170 B.155 p.15 1.3171 B.156 p.15 1.3172 B.157 p.15 1.3173 B.158 p.15 1.3174 B.159 p.15 1.3175 B.160 p.15 1.3176 B.161 p.15 1.3177 B.162 p.15 1.3178 B.163 p.15 1.3179 B.164 p.15 1.3180 B.165 p.15 1.3181 B.166 p.15 1.3182 B.167 p.15 1.3183 B.168 p.15 1.3184 B.169 p.15 1.3185 B.170 p.15 1.3186 B.171 p.15

1.3187 B.172 p.15 1.3188 B.173 p.15 1.3189 B.174 p.15 1.3190 B.175 p.15 1.3191 B.176 p.15 1.3192 B.177 p.15 1.3193 B.178 p.15 1.3194 B.179 p.15 1.3195 B.180 p.15 1.3196 B.181 p.15 1.3197 B.182 p.15 1.3198 B.183 p.15 1.3199 B.184 p.15 1.3200 B.185 p.15 1.3201 B.186 p.15 1.3202 B.187 p.15 1.3203 B.188 p.15 1.3204 B.189 p.15 1.3205 B.190 p.15 1.3206 B.191 p.15 1.3207 B.192 p.15 1.3208 B.193 p.15 1.3209 B.194 p.15 1.3210 B.195 p.15 1.3211 B.196 p.15 1.3212 B.197 p.15 1.3213 B.198 p.15 1.3214 B.199 p.15 1.3215 B.200 p.15 1.3216 B.201 p.15

1.3217 IN 1 p.16 1.3218 AT 2 p.16 1.3219 B.3 p.16 1.3220 AT 4 p.16 1.3221 AT 5 p.16 1.3222 AT 6 p.16 1.3223 AT 7 p.16 1.3224 AT 8 p.16 1.3225 AT 9 p.16 1.3226 AT 10 p.16 1.3227 in and p.16 1.3228 AT 12 p.16

1.3229 B.13 p.16 1.3230 B.14 p.16 1.3231 B.15 p.16 1.3232 B.16 p.16 1.3233 B.17 p.16 1.3234 B.18 p.16 1.3235 B.19 p.16 1.3236 IN 20 p.16 1.3237 AT 21 p.16 1.3238 B.22 p.16 1.3239 B.23 p.16 1.3240 B.24 p.16

1.3241 B.25 p.16 1.3242 B.26 p.16 1.3243 B.27 p.16 1.3244 B.28 p.16 1.3245 B.29 p.16 1.3246 B.30 p.16 1.3247 B.31 p.16 1.3248 B.32 p.16 1.3249 B.33 p.16 1.3250 B.34 p.16 1.3251 B.35 p.16 1.3252 B.36 p.16

- 46 042660

1.3253 B.37 p.16 1.3301 B.85 p.16 1.3349 B.133 p.16 1.3254 B.38 p.16 1.3302 B.86 p.16 1.3350 B.134 p.16 1.3255 B.39 p.16 1.3303 B.87 p.16 1.3351 B.135 p.16 1.3256 B.40 p.16 1.3304 B.88 p.16 1.3352 B.136 p.16 1.3257 B.41 p.16 1.3305 B.89 p.16 1.3353 B.137 p.16 1.3258 B.42 p.16 1.3306 B.90 p.16 1.3354 B.138 p.16 1.3259 B.43 p.16 1.3307 B.91 p.16 1.3355 B.139 p.16 1.3260 B.44 p.16 1.3308 B.92 p.16 1.3356 B.140 p.16 1.3261 B.45 p.16 1.3309 B.93 p.16 1.3357 B.141 p.16 1.3262 B.46 p.16 1.3310 B.94 p.16 1.3358 B.142 p.16 1.3263 B.47 p.16 1.3311 B.95 p.16 1.3359 B.143 p.16 1.3264 B.48 p.16 1.3312 B.96 p.16 1.3360 B.144 p.16 1.3265 B.49 p.16 1.3313 B.97 p.16 1.3361 B.145 p.16 1.3266 B.50 p.16 1.3314 B.98 p.16 1.3362 B.146 p.16 1.3267 B.51 p.16 1.3315 B.99 p.16 1.3363 B.147 p.16 1.3268 B.52 p.16 1.3316 B.100 p.16 1.3364 B.148 p.16 1.3269 B.53 p.16 1.3317 B.101 p.16 1.3365 B.149 p.16 1.3270 B.54 p.16 1.3318 B.102 p.16 1.3366 B.150 p.16 1.3271 B.55 p.16 1.3319 B.103 p.16 1.3367 B.151 p.16 1.3272 B.56 p.16 1.3320 B.104 p.16 1.3368 B.152 p.16 1.3273 B.57 p.16 1.3321 B.105 p.16 1.3369 B.153 p.16 1.3274 B.58. p.16 1.3322 B.106 p.16 1.3370 B.154 p.16 1.3275 B.59 p.16 1.3323 B.107 p.16 1.3371 B.155 p.16 1.3276 B.60 p.16 1.3324 B.108 p.16 1.3372 B.156 p.16 1.3277 B.61 p.16 1.3325 B.109 p.16 1.3373 B.157 p.16 1.3278 B.62 p.16 1.3326 B.110 p.16 1.3374 B.158 p.16 1.3279 B.63 p.16 1.3327 B.111 p.16 1.3375 B.159 p.16 1.3280 B.64 p.16 1.3328 B.112 p.16 1.3376 B.160 p.16 1.3281 B.65 p.16 1.3329 V.IZ p.16 1.3377 B.161 p.16 1.3282 B.66 p.16 1.3330 B.114 p.16 1.3378 B.162 p.16 1.3283 B.67 p.16 1.3331 B.115 p.16 1.3379 B.163 p.16 1.3284 B.68 p.16 1.3332 B.116 p.16 1.3380 B.164 p.16 1.3285 B.69 p.16 1.3333 B.117 p.16 1.3381 B.165 p.16 1.3286 B.70 p.16 1.3334 B.118 p.16 1.3382 B.166 p.16 1.3287 B.71 p.16 1.3335 B.119 p.16 1.3383 B.167 p.16 1.3288 B.72 p.16 1.3336 B.120 p.16 1.3384 B.168 p.16 1.3289 B.73 p.16 1.3337 B.121 p.16 1.3385 B.169 p.16 1.3290 B.74 p.16 1.3338 B.122 p.16 1.3386 B.170 p.16 1.3291 B.75 p.16 1.3339 B.123 p.16 1.3387 B.171 p.16 1.3292 B.76 p.16 1.3340 B.124 p.16 1.3388 B.172 p.16 1.3293 B.77 p.16 1.3341 B.125 p.16 1.3389 B.173 p.16 1.3294 B.78 p.16 1.3342 B.126 p.16 1.3390 B.174 p.16 1.3295 B.79 p.16 1.3343 B.127 p.16 1.3391 B.175 p.16 1.3296 B.80 p.16 1.3344 B.128 p.16 1.3392 B.176 p.16 1.3297 B.81 p.16 1.3345 B.129 p.16 1.3393 B.177 p.16 1.3298 B.82 p.16 1.3346 B.130 p.16 1.3394 B.178 p.16 1.3299 B.83 p.16 1.3347 B.131 p.16 1.3395 B.179 p.16 1.3300 B.84 p.16 1.3348 B.132 p.16 1.3396 B.180 p.16

- 47 042660

1.3397 B.181 p.16 1.3398 B.182 p.16 1.3399 B.183 p.16 1.3400 B.184 p.16 1.3401 B.185 p.16 1.3402 B.186 p.16 1.3403 B.187 p.16

1.3404 B.188 p.16 1.3405 B.189 p.16 1.3406 B.190 p.16 1.3407 B.191 p.16 1.3408 B.192 p.16 1.3409 B.193 p.16 1.3410 B.194 p.16

1.3411 B.195 p.16 1.3412 B.196 p.16 1.3413 B.197 p.16 1.3414 B.198 p.16 1.3415 B.199 p.16 1.3416 B.200 p.16 1.3417 B.201 p.16

1.3418 IN 1 p.17 1.3419 AT 2 p.17 1.3420 v.z p.17 1.3421 AT 4 p.17 1.3422 AT 5 p.17 1.3423 AT 6 p.17 1.3424 AT 7 p.17 1.3425 AT 8 p.17 1.3426 AT 9 p.17 1.3427 AT 10 p.17 1.3428 IN AND p.17 1.3429 AT 12 p.17 1.3430 B.13 p.17 1.3431 B.14 p.17 1.3432 B.15 p.17 1.3433 B.16 p.17 1.3434 B.17 p.17 1.3435 B.18 p.17 1.3436 B.19 p.17 1.3437 IN 20 p.17 1.3438 AT 21 p.17 1.3439 B.22 p.17 1.3440 B.23 p.17 1.3441 B.24 p.17 1.3442 B.25 p.17 1.3443 B.26 p.17 1.3444 B.27 p.17 1.3445 B.28 p.17 1.3446 B.29 p.17 1.3447 B.30 p.17 1.3448 B.31 p.17 1.3449 B.32 p.17 1.3450 B.33 p.17 1.3451 B.34 p.17 1.3452 B.35 p.17 1.3453 B.36 p.17 1.3454 B.37 p.17 1.3455 B.38 p.17

1.3456 B.39 p.17 1.3457 B.40 p.17 1.3458 B.41 p.17 1.3459 B.42 p.17 1.3460 B.43 p.17 1.3461 B.44 p.17 1.3462 B.45 p.17 1.3463 B.46 p.17 1.3464 B.47 p.17 1.3465 B.48 p.17 1.3466 B.49 p.17 1.3467 B.50 p.17 1.3468 B.51 p.17 1.3469 B.52 p.17 1.3470 B.53 p.17 1.3471 B.54 p.17 1.3472 B.55 p.17 1.3473 B.56 p.17 1.3474 B.57 p.17 1.3475 B.58. p.17 1.3476 B.59 p.17 1.3477 B.60 p.17 1.3478 B.61 p.17 1.3479 B.62 p.17 1.3480 B.63 p.17 1.3481 B.64 p.17 1.3482 B.65 p.17 1.3483 B.66 p.17 1.3484 B.67 p.17 1.3485 B.68 p.17 1.3486 B.69 p.17 1.3487 B.70 p.17 1.3488 B.71 p.17 1.3489 B.72 p.17 1.3490 B.73 p.17 1.3491 B.74 p.17 1.3492 B.75 p.17 1.3493 B.76 p.17

1.3494 B.77 p.17 1.3495 B.78 p.17 1.3496 B.79 p.17 1.3497 B.80 p.17 1.3498 B.81 p.17 1.3499 B.82 p.17 1.3500 B.83 p.17 1.3501 B.84 p.17 1.3502 B.85 p.17 1.3503 B.86 p.17 1.3504 B.87 p.17 1.3505 B.88 p.17 1.3506 B.89 p.17 1.3507 B.90 p.17 1.3508 B.91 p.17 1.3509 B.92 p.17 1.3510 B.93 p.17 1.3511 B.94 p.17 1.3512 B.95 p.17 1.3513 B.96 p.17 1.3514 B.97 p.17 1.3515 B.98 p.17 1.3516 B.99 p.17 1.3517 B.100 p.17 1.3518 B.101 p.17 1.3519 B.102 p.17 1.3520 B.103 p.17 1.3521 B.104 p.17 1.3522 B.105 p.17 1.3523 B.106 p.17 1.3524 B.107 p.17 1.3525 B.108 p.17 1.3526 B.109 p.17 1.3527 B.110 p.17 1.3528 B.111 p.17 1.3529 B.112 p.17 1.3530 V.IZ p.17 1.3531 B.114 p.17

- 48 042660

1.3532 B.115 C.17 1.3533 B.116 C.17 1.3534 B.117 C.17 1.3535 B.118 C.17 1.3536 B.119 C.17 1.3537 B.120 C.17 1.3538 B.121 C.17 1.3539 B.122 C.17 1.3540 B.123 C.17 1.3541 B.124 C.17 1.3542 B.125 C.17 1.3543 B.126 C.17 1.3544 B.127 C.17 1.3545 B.128 C.17 1.3546 B.129 C.17 1.3547 B.130 C.17 1.3548 B.131 C.17 1.3549 B.132 C.17 1.3550 B.133 C.17 1.3551 B.134 C.17 1.3552 B.135 C.17 1.3553 B.136 C.17 1.3554 B.137 C.17 1.3555 B.138 C.17 1.3556 B.139 C.17 1.3557 B.140 C.17 1.3558 B.141 C.17 1.3559 B.142 C.17 1.3560 B.143 C.17

1.3561 B.144 C.17 1.3562 B.145 C.17 1.3563 B.146 C.17 1.3564 B.147 C.17 1.3565 B.148 C.17 1.3566 B.149 C.17 1.3567 B.150 C.17 1.3568 B.151 C.17 1.3569 B.152 C.17 1.3570 B.153 C.17 1.3571 B.154 C.17 1.3572 B.155 C.17 1.3573 B.156 C.17 1.3574 B.157 C.17 1.3575 B.158 C.17 1.3576 B.159 C.17 1.3577 B.160 C.17 1.3578 B.161 C.17 1.3579 B.162 C.17 1.3580 B.163 C.17 1.3581 B.164 C.17 1.3582 B.165 C.17 1.3583 B.166 C.17 1.3584 B.167 C.17 1.3585 B.168 C.17 1.3586 B.169 C.17 1.3587 B.170 C.17 1.3588 B.171 C.17 1.3589 B.172 C.17

1.3590 B.173 C.17 1.3591 B.174 C.17 1.3592 B.175 C.17 1.3593 B.176 C.17 1.3594 B.177 C.17 1.3595 B.178 C.17 1.3596 B.179 C.17 1.3597 B.180 C.17 1.3598 B.181 C.17 1.3599 B.182 C.17 1.3600 B.183 C.17 1.3601 B.184 C.17 1.3602 B.185 C.17 1.3603 B.186 C.17 1.3604 B.187 C.17 1.3605 B.188 C.17 1.3606 B.189 C.17 1.3607 B.190 C.17 1.3608 B.191 C.17 1.3609 B.192 C.17 1.3610 B.193 C.17 1.3611 B.194 C.17 1.3612 B.195 C.17 1.3613 B.196 C.17 1.3614 B.197 C.17 1.3615 B.198 C.17 1.3616 B.199 C.17 1.3617 B.200 C.17 1.3618 B.201 C.17

1.3619 -- C.l 1.3620 -- C.2 1.3621 -- C.3 1.3622 -- C.4 1.3623 -- C.5 1.3624 -- C.6

1.3625 -- C.7 1.3626 -- C.8 1.3627 -- C.9 1.3628 -- C.10 1.3629 -- C.ll 1.3630 -- C.12

1.3631 -- C.13 1.3632 -- C.14 1.3633 -- C.15 1.3634 -- C.16 1.3635 -- C.17

In addition, it may be advantageous to use the benzoxaborole compounds of formula (I) alone or in combination with other herbicides or as a mixture with other crop protection agents, for example together with pest control agents or phytopathogenic fungi or bacteria. Also of interest is miscibility with mineral salt solutions that are used to treat nutritional and micronutrient deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.

The invention also relates to agrochemical compositions containing at least an excipient and at least one benzoxaborol compound of formula (I) according to the invention.

The agrochemical composition contains a pesticidally effective amount of a benzoxaborole compound of formula (I). The term "effective amount" means an amount of the composition or compounds I which is sufficient to control unwanted plants, especially to control unwanted plants in cultivated plants, and which does not result in significant damage to the treated plants. Such an amount may vary over a wide range and depends on various factors such as the plants to be controlled, the cultivated plant or material being treated, the climatic conditions and the particular benzoxaborol compound of formula (I) used.

The benzoxaborole compound of formula (I), its N-oxides or salts can be formulated into conventional types of agrochemical compositions, for example solutions, emulsions, suspensions, dusting powders, powders, pastes, granules, compresses, capsules and mixtures thereof. Examples for types of agrochemical formulations are suspensions (eg SC, OD, FS), emulsifiable concentrates (eg EC), emulsions (eg EW, EO, ES, ME), capsules (eg CS, ZC), pastes, lozenges, wettable or dusting powders (e.g. WP, SP, WS, DP, DS), pressed articles (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG) , insecticidal products (eg LN) as well as gel formulations for the treatment of plant propagation materials such as seeds (eg GF). These and additional types of agrochemical compositions are defined in the Catalog of pesticide formulation types and international coding system, Technical Monograph No. 2, 6th ed. May 2008, CropLife International.

- 49 042660

Agrochemical compositions are prepared in a known manner, as described in Mollet and Grubemann,

Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

Suitable excipients are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersing agents, emulsifying agents, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesive agents, thickeners, wetting agents, repellants , attractants, eating stimulants, compatibilizers, bactericides, antifreezes, antifoam agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents such as medium to high boiling fractions of petroleum, eg kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example, toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, eg ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, eg lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acid; phosphonates; amines; amides, eg N-methylpyrrolidone, fatty acid dimethylamides; and their mixtures.

Suitable solid carriers or fillers are mineral earths, for example, silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, eg cellulose, starch; fertilizers, eg ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; vegetable products such as cereal flour, tree bark flour, wood flour, nutshell flour, and mixtures thereof.

Suitable surfactants are surface active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as an emulsifying agent, dispersant, solubilizer, wetting agent, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International ed. or North American ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts-sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alphaolefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated arylphenol sulfonates, condensed naphthalenes sulfonates, dodecyl and tridecylbenzene sulfonates, naphthalenes and alkylnaphthalenes or sulfosuccinates sulfonates. Examples of sulfates are sulfates of fatty acids and oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates are esters of phosphoric acid. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable non-ionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1-50 equivalents. For alkoxylation, ethylene oxide and/or propylene oxide, preferably ethylene oxide, can be used. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose-glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or long chain primary amine salts. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are type A-B or type A-B-A, which contain blocks of polyethylene oxide and polypropylene oxide, or type A-B-C, which contain alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkaline salts of polyacrylic acid or comb polymers of polyacids. Examples of polybases are polyvinylamines or polyethyleneamines.

- 50 042660

Suitable adjuvants are compounds which have little or no pesticidal activity and which improve the biological effectiveness of Compound I against the target. Examples are surfactants, mineral or vegetable oils and other excipients. Additional examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or not), polycarboxylates and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

Suitable antifreezes are ethylene glycol, propylene glycol, urea and glycerin.

Suitable antifoam agents are silicones, long chain alcohols and fatty acid salts.

Suitable colorants (eg red, blue, or green) are pigments of low water solubility and water-soluble colorants. Examples are inorganic dyes (eg iron oxide, titanium oxide, iron hexacyanoferrate) and organic dyes (eg alizarin, azo and phthalocyanine dyes).

Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples of types of agrochemical composition and their production.

i) Water soluble concentrates (SL, LS).

10-60% by weight of a benzoxaborole compound of formula (I) according to the invention and 5-278% by weight of a wetting agent (eg alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (eg alcohols) up to 100% by weight . The active substance dissolved on dilution with water.

ii) Dispersible concentrates (DC).

5-25% by weight of a benzoxaborole compound of formula (I) according to the invention and 1-10% by weight of a dispersant (eg polyvinylpyrrolidone) were dissolved in an organic solvent (eg cyclohexanone) up to 100% by weight. Dilution with water gave a dispersion.

iii) Emulsifiable concentrates (EC).

278-70 wt.% of the benzoxaborol compound of formula (I) in accordance with the invention and 5-10 wt.% emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) were dissolved in a water-insoluble organic solvent (for example, an aromatic hydrocarbon) to 100 wt. .%. When diluted with water, an emulsion was formed.

iv) Emulsions (EW, EO, ES).

5-40% by weight of a benzoxaborole compound of formula (I) according to the invention and 1-10% by weight of emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40% by weight of a water-insoluble organic solvent (for example, aromatic hydrocarbon). This mixture was introduced into water up to 100 wt.% using an emulsifying device and brought to a homogeneous emulsion. When diluted with water, an emulsion was formed.

v) Suspensions (SC, OD, FS).

In a ball mill with a stirrer, 20-60 wt.% of the benzoxaborol compound of formula (I) in accordance with the invention was ground with the addition of 2-10 wt.% dispersants and wetting agents (for example, sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt.% thickener (eg xanthan gum) and water up to 100 wt.% to obtain a thin suspension of the active substance. When diluted with water, a stable suspension of active substances was formed. For an FS type composition, up to 40% by weight of a binder (eg, polyvinyl alcohol) was added.

vi) Water-dispersible granules and water-soluble granules (WG, SG).

50-80 wt.% of the benzoxaborole compound of formula (I) according to the invention is finely ground with the addition of dispersants and wetting agents (for example, sodium lignosulfonate and alcohol ethoxylate) to 100 wt.% and obtained in the form of water-dispersible or water-soluble granules using technical equipment (eg extrusion, spray tower, fluidized bed). When diluted with water, a stable dispersion or solution of active substances was formed.

vii) Water-dispersible powders and water-soluble powders (WP, SP, WS).

50-80 wt.% of the benzoxaborol compound of formula (I) in accordance with the invention was ground in a rotor-stator mill with the addition of 1-5 wt.% dispersants (for example, sodium lignosulfonate), 1-3 wt.% wetting agents (for example, ethoxylate alcohol) and a solid carrier, for example, silica gel, up to 100 wt.%. When diluted with water, a stable dispersion or solution of active substances was formed.

viii) Gel (GW, GF).

In a ball mill with a stirrer, 5-25 wt.% of the benzoxaborol compound of formula (I) in accordance with the invention was ground with the addition of 3-10 wt.% dispersants (for example, sodium lignosulfonate), 1-5 wt.% thickener (for example, carboxymethyl cellulose) and water up to 100 wt.% to obtain a thin suspension of the active substance. When diluted with water, a stable suspension of the active substance was formed.

iv) Microemulsion (ME).

5-20% by weight of a benzoxaborole compound of formula (I) according to the invention was added to 530% by weight of an organic solvent mixture (e.g. fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a mixture of surfactants (e.g. ethoxylate alcohol and arylphenol ethoxylate), and water up to 100%. This mixture was stirred for 1 hour, spontaneously obtaining a thermodynamically stable microemulsion.

iv) Microcapsules (CS).

An oil phase containing 5-50% by weight of a benzoxaborole compound of formula (I) according to the invention, 0-40% by weight of a water-insoluble organic solvent (e.g. aromatic hydrocarbon), 2-278% by weight of acrylic monomers (e.g. methyl methacrylate, methacrylic acid, and di- or triacrylate) were dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol. Radical polymerization resulted in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5-50 wt.% of a benzoxaborole compound of the formula ( I) according to the invention, 0-40% by weight of a water-insoluble organic solvent (e.g. aromatic hydrocarbon) and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanate) are dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol.) The addition of a polyamine (eg, hexamethylenediamine) resulted in the formation of polyurea microcapsules. The amount of monomers was 1-10 wt.%. The wt.% refers to the total CS composition.

ix) Dust-like powders (DP, DS).

1-10 wt.% of the compounds of benzoxaborol formula (I) in accordance with the invention finely divided and thoroughly mixed with a solid carrier (for example, finely divided kaolin), up to 100 wt.%.

x) Granules (GR, FG).

0.5-30% by weight of a benzoxaborole compound of formula (I) according to the invention is finely ground and combined with a solid carrier (eg silicate) up to 100% by weight. Granulation was achieved by extrusion, spray drying or fluid bed.

xi) Ultra Low Volume (UL) fluids.

1-50% by weight of a benzoxaborole compound of formula (I) according to the invention is dissolved in an organic solvent (eg an aromatic hydrocarbon), up to 100% by weight.

Agrochemical composition types i)-xi) may optionally contain additional adjuvants such as 0.1-1 wt.% bactericides, 5-278 wt.% antifreezes, 0.1-1 wt.% antifoam agents and 0.1-1 wt.% dyes.

Agrochemical compositions usually contain between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of the benzoxaborol compounds of formula (I). The benzoxaborole compounds of formula (I) are used in a purity of 90 to 100%, preferably 95 to 100% (according to NMR spectrum).

Seed treatment solutions (LS), suspoemulsions (SE), fluid concentrates (FS), dry treatment powders (DS), water-dispersible slurry treatment powders (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are commonly used to treat plant propagation materials, especially seeds. The agrochemical compositions in question, after two to tenfold dilution, provide an active substance concentration of 0.01 to 60% by weight, preferably 0.1 to 40% by weight, in ready-to-use preparations. The application can be carried out before or during sowing.

Methods for applying the benzoxaborole compounds of formula (I), or agrochemical compositions thereof, to plant propagation material, especially seeds, include dressing, coating, pelletizing, dusting, and soaking, as well as methods of applying the propagation material to the grooves. Preferably, Compound I or compositions thereof, respectively, is applied to the plant propagation material in such a manner that germination is not induced, for example by seed dressing, pelletizing, coating and dusting.

Various types of oils, wetting agents, adjuvants, fertilizers, or trace elements, and other pesticides (for example, herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the benzoxaborol compounds of formula (I) or to agrochemical compositions that contain them, in as a premix or, if necessary, a non-immediate use agent (tank mix). These agents can be mixed with the agrochemical compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the benzoxaborole compounds of formula (I) according to the invention or agrochemical compositions containing them, usually from a pre-application preparation device, backpack sprayer, spray tank, spray unit, or

- 52 042660 irrigation systems. As a rule, the agrochemical composition is diluted with water, buffer, and/or other excipients to the desired concentration for use and thus a ready-to-use spray solution or agrochemical composition according to the invention is obtained. As a rule, from 20 to

2000 l, preferably 50 to 400 l ready to use spray solution.

According to one embodiment, either the individual components of the agrochemical compositions according to the invention or partially pre-mixed components, for example components containing azines of formula (I) can be mixed by the user in the spray tank and, if necessary, additional excipients can be added.

In a further embodiment, the individual components of the agrochemical compositions according to the invention, such as parts of a kit or parts of a two-or three-component mixture, can be mixed by the user in a spray tank and, if necessary, additional excipients can be added.

In a further embodiment, either individual components of the agrochemical compositions according to the invention or partially premixed components, for example components containing benzoxaborole compounds of formula (I), may be applied together (eg in the case of a tank mix) or sequentially.

The benzoxaborole compounds of formula (I) are useful as herbicides. They are suitable as such or in the form of a suitably formulated composition (agrochemical composition).

The benzoxaborole compounds of formula (I), or agrochemical compositions containing azines of formula (I), allow very effective control of vegetation in non-crop areas, especially at high application rates. They act against broadleaf weeds and weeds in crops such as wheat, rice, maize, soybeans and cotton without causing any significant damage to crop plants. This effect is observed mainly at low flow rates.

The benzoxaborol compounds of formula (I), or agrochemical compositions containing them, are applied to plants mainly by foliar spraying or to the soil in which the seeds of the plants have been sown. In this case, the application can be carried out using, for example, water as a carrier by conventional spraying techniques, using a spray solution in an amount of from about 100 to 1000 l/ha (for example, from 300 to 400 l/ha). The benzoxaborole compounds of formula (I), or agrochemical compositions containing them, can also be applied in a low volume or ultra low volume process or as microgranules.

The application of the benzoxaborole compounds of formula (I), or agrochemical compositions containing them, can be carried out before, during and/or after the germination of unwanted plants.

The benzoxaborole compounds of formula (I), or agrochemical compositions containing them, can be applied pre-emergence or post-emergence, or before sowing, or together with the seeds of the crop plant. It is also possible to apply benzoxaborole compounds of formula (I), or agrochemical compositions containing them, using crop plant seeds pre-treated with a benzoxaborole compound of formula (I) or agrochemical compositions containing them. If the active ingredients are less tolerant to certain crop plants, application techniques may be employed in which the herbicidal compositions are sprayed with spray equipment in such a way that, as far as possible, they do not come into contact with the leaves of sensitive crop plants while how the active compounds reach the leaves of unwanted plants growing underneath or the bare soil surface (post-directed, lay-by).

In a further embodiment, the benzoxaborol compounds of formula (I), or agrochemical compositions containing them, can be applied by seed treatment. Seed treatment includes essentially all techniques known to the person skilled in the art (seeding, coating, spraying, soaking, film coating, multilayer coating, thin coating, dropping and pelletizing) based on benzoxaborole compounds of formula (I), or agrochemical compositions prepared from them. In this case, the herbicidal compositions can be applied diluted or undiluted.

The term seeds includes seeds of all types, such as, for example, grains, seeds, fruits, tubers, seedlings, and the like. Here, the term seeds preferably describes grains and seeds. The seeds used may be the seeds of the useful plants mentioned above, as well as the seeds of transgenic plants or plants obtained by conventional breeding methods.

When used in plant protection, the amount of active substances used, i.e. compounds of benzoxaborole of formula (I), without formulation auxiliaries, are, depending on the desired effect, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.005 to 0.9 kg per ha and, in in particular, from 0.05 to 0.5 kg per ha.

In another embodiment of the invention, the application rate of the benzoxaborole compound of formula (I) is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha, active substance (a.v.).

- 53 042660

In another preferred embodiment of the invention, the application rates of the benzoxaborole compounds of formula (I) according to the present invention (total amount of benzoxaborole compounds of formula (I)) are from 0.1 g/ha to 3000 g/ha, preferably from 10 g/ha to 1000 g/ ha, depending on the target to be controlled, the season, target plants and growth stage.

In another preferred embodiment of the invention, application rates of the benzoxaborole compounds of formula (I) are in the range of 0.1 g/ha to 5000 g/ha and preferably in the range of 1 to 2500 g/ha or 5 to 2000 g/ha.

In another preferred embodiment of the invention, the application rates of the benzoxaborole compounds of formula (I) are from 0.1 to 1000 g/ha, preferably from 1 to 750 g/ha, more preferably from 5 to 500 g/ha.

When treating plant propagation materials such as seeds, for example by spraying, coating or impregnating seeds, the amounts of active substance required are from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kg of plant propagation material (preferably seeds).

In another embodiment of the invention, for seed treatment, the amount of active substances applied, i.e. benzoxaborole compounds of formula (I) are usually used in amounts of from 0.001 to 10 kg per 100 kg of seeds.

When used to protect materials or stored products, the amount of active substance used depends on the type of application and on the desired effect. Amounts commonly used in the protection of materials are from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active substance per cubic meter of material to be treated.

Depending on the method of application in question, the benzoxaborol compounds of formula (I), or agrochemical compositions containing them, can additionally be used in additional crop plants to kill unwanted plants. Examples of suitable crops are as follows:

Allium sulfur, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena saliva, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, 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) sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca , Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes Sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

Preferred crops are

Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Horgiadeum vulgare, Jugiadeum Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale , Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

Particularly preferred crops are cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts or perennial crops.

- 54 042660

The benzoxaborole compounds of formula (I) according to the invention, or agrochemical compositions containing them, can also be used in genetically modified plants. The term genetically modified plants should be understood to mean plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted DNA sequence that is not native to the genome of such plant species or to exhibit a deletion of DNA that is native to the genome of such species, whereby such modification(s) cannot easily be obtained by cross-breeding, mutagenesis or purely natural recombination. Often, a single genetically modified plant is a plant that has obtained its genetic modification(s) by inheritance through natural breeding or propagation from a generic plant whose genome has been directly processed using recombinant DNA techniques. As a rule, one or more genes are integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include, but are not limited to, targeted post-translational modification of protein(s), oligo- or polypeptides, for example, by incorporating amino acid mutation(s) into them that allows, reduces, or promotes the process of glycosylation or polymer attachment, such as prenylation, acetylation or attachment of PEG moieties.

Plants that have been modified by breeding, mutagenesis, or genetic engineering, for example, have been resistant to specific herbicide classes, such as auxin herbicides such as dicamba or 2,4-D; bleaching herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylurea or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynyl (ie bromoxynyl or ioxynyl) herbicides as a result of conventional breeding or genetic engineering methods; in addition, plants have been conferred resistance to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate, or both glyphosate and a herbicide from another class, such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide tolerance technologies are, for example, described in Pest Management Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61, 2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1185; and the links they contain. Several cultivated plants have been made resistant to herbicides by mutagenesis and conventional breeding methods, e.g. Clearfield® summer rapeseed (Canola, BASF SE, Germany) made resistant to imidazolinones, e.g. imazamox, or ExpressSun® sunflower (DuPont, USA) made resistant to sulfonylureas such as tribenuron. Genetic engineering techniques have been used to make crop plants such as soybeans, cotton, corn, beets and canola tolerant to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are under development or commercially available under the RoundupReady® brands or trade names. (glyphosate-tolerant, Monsanto, USA), Cultivance® (imidazolinone-tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).

In addition, also included are plants which, through the use of recombinant DNA technologies, are capable of synthesizing one or more insecticidal proteins, which are mainly known from the bacterial genus Bacillus, in particular from Bacillus thuringiensis, such as deltaendotoxins, for example, CryIA(b), CryIA(c ), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetable insecticidal proteins (VIPs), eg VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of nematode colonizing bacteria, eg Photorhabdus spp. or Xenorhabdus spp.; animal-produced toxins such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi such as streptomycete toxins, plant lectins such as pea or barley lectins; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, luffin, saporin, or bryodin; steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors or HMGCoA reductase; ion channel blockers such as sodium or calcium channel blockers; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinase and glucanase. In the context of the present invention, these insecticidal proteins or toxins should be clearly understood as also pretoxins, fusion proteins, truncated or otherwise modified proteins. Fusion proteins are distinguished by a novel combination of protein domains (see, for example, WO 02/0278701). Further examples of such toxins or genetically

- 55 042660 modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03/52073. Methods for obtaining such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the above publications. These insecticidal proteins, found in genetically modified plants, confer resistance to pests from all taxonomic groups of arthropods, in particular to beetles (Coeloptera), dipterans (Diptera), and butterflies (Lepidoptera), as well as to plants producing these proteins. nematodes (Nematoda). Genetically modified plants capable of synthesizing one or more insecticidal proteins are described, for example, in the above publications, and some of them are commercially available, such as YieldGard® (Cry1Ab toxin producing corn cultivars), YieldGard® Plus (Cry1Ab toxin producing corn cultivars). Cry1Ab and Cry3Bb1), Starlink® (corn cultivars producing Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1, Cry35Ab1 and phosphinothricin-I-acetyltransferase [PAT] enzyme); NuCOTN® 33B (cotton cultivars producing CrylAc toxin), Bollgard® I (cotton cultivars producing CrylAc toxin), Bollgard® II (cotton cultivars producing Oy1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing VIP toxin); NewLeaf® (potato cultivars producing Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Btll (e.g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing CrylAb toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, see WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars, producing a modified version of Cry1Ac toxin) and 27807 from Pioneer Overseas Corporation, Belgium (maize cultivars producing Cry1F toxin and PAT enzyme).

Also included are plants that, through the use of recombinant DNA techniques, are capable of synthesizing one or more proteins to increase the resistance or tolerance of such plants against bacterial, viral, or fungal pathogens. Examples of such proteins are the so-called pathogenesis-related proteins (PR proteins, see e.g. EP-A 392 225), plant disease resistance genes (e.g. potato cultivars which express resistance genes active against Phytophthora infestans pathogens derived from Mexican wild potato, Solanum bulbocastanum) or T4-lysozyme (e.g. potato cultivars that are able to synthesize these proteins with increased resistance to bacteria such as Erwinia amylovora). Methods for obtaining such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the above publications.

Also included are plants that, through the use of recombinant DNA techniques, are capable of synthesizing one or more proteins to improve productivity (e.g., biomass production, grain yield, starch, oil, or protein content), tolerance to drought, salinity, or other growth-limiting factors. environment, or tolerance against pests and fungal, bacterial or viral pathogens of said plants.

Also included are plants that, through the use of recombinant DNA technology, contain modified amounts of ingredients or new ingredients, especially for improving human and animal nutrition, such as oilseed crops that produce healthy long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (eg, canola, Nexera®, Dow AgroSciences, Canada).

In addition, plants are also included which, through the use of recombinant DNA technologies, contain a modified amount of ingredients contained or new ingredients, in particular to improve the production of raw materials, for example, potatoes, which produce increased amounts of amylopectin (for example, potatoes Amflora®, BASF SE, Germany).

Another embodiment of the invention is a method for controlling unwanted vegetation, which includes providing a herbicidally active amount of at least one compound of formula (I), as defined above, to the plants, environment or seeds.

The preparation of benzoxaborole compounds of formula (I) is exemplified; however, the subject matter of the present invention is not limited to the examples given.

The products shown below are characterized by mass ([m/z]) or retention time (RT; [min]) determined by HPLC-MS spectrometry.

HPLC-MS = high performance liquid chromatography combined with mass spectrometry; HPLC column:

- 56 042660

RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50x4.6 mm; mobile phase: acetonitrile + 0.1% trifluoroacetic acid (TFA) / water + 0.1% TFA using a gradient from 5:95 to

100:0 for 5 min at 40°C, flow rate 1.8 ml/min.

MS: quadrupole electrospray ionization, 80 V (positive ion detection mode).

The following abbreviations are used.

CH ₂ Cl ₂ : dichloromethane,

EtOAc: Acetic acid ethyl ester,

THF: tetrahydrofuran,

CH: cyclohexane,

HCl: hydrogen chloride,

NaOH: sodium hydroxide,

DMF: N,N-dimethylformamide,

HPLC: high pressure chromatography,

LC: liquid chromatography,

MS: mass spectrometry,

KOAc: potassium acetate,

Dppf: 1,1'-bis(diphenylphosphino)-ferrocene,

MeOH: methanol,

MTBE: Methyl tert-butyl ether,

PE: petroleum ether,

TFA: trifluoroacetic acid.

A. Examples of receipt.

1) ethyl 4-bromo-5-formyl-1,3-benzodioxol-2-carboxylate

A mixture of 2-bromo-3,4-dihydroxybenzaldehyde (CAS 4815-97-8) (1.6 g, 7.4 mmol), 2,2-dibromoacetic acid ethyl ester (3.6 g, 14.8 mmol), K ₂ CO ₃ (2 g, 14.8 mmol) in DMF (20 mL) was heated to 100°C for 2 h. The reaction was quenched by adding H2O, extracted with EtOAc, and the combined organic phase was washed with brine. The organic layer was dried over anhydrous Na ₂ SO ₄ , filtered and concentrated. The residue was purified on a column to give ethyl 4-bromo-5-formyl-1,3-benzodioxol-2-carboxylate (1 g, 45%) as a yellow solid.

¹ H NMR: CDCl ₃ 400 MHz δ 10.16 (d, J=1.51 Hz, 1H) 7.61 (dd, J=8.28, 1.76 Hz, 1H) 6.93 (d, J=8.16 Hz, 1H) 6.47 (s, 1H) 4.30-4.40 (m, 2H) 1.32-1.39 (m, 3H).

2) ethyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-formyl-1,3-benzodioxol-2-carboxylate

A mixture of ethyl 4-bromo-5-formyl-1,3-benzodioxol-2-carboxylate (2.7 g, 9 mmol), 2-(5,5-dimethyl1,3,2-dioxaborinan-2-yl)-5.5 -dimethyl-1,3,2-dioxaborinan (3.4 g, 13.5 mmol), KOAc (2.6 g, 27 mmol) and Pd(dppf)Cl ₂ (270 mg) in dioxane (30 ml) were heated to 80°C for 2 h under N ₂ . The reaction was quenched by adding H ₂ O, extracted with EtOAc and the combined organic phase was washed with brine. The organic layer was dried over anhydrous Na ₂ SO ₄ , filtered and concentrated. The residue was purified on a column to give ethyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-formyl-1,3-benzodioxol-2-carboxylate (1.8 g, 66%) as yellow solid.

1H NMR: CDCl ₃ 400 MHz δ 9.85 (s, 1H) 7.43 (d, J=7.91 Hz, 1H) 6.95 (d, J=8.03 Hz, 1H) 6.37 (s, 1H) 4.32 (q, J=6.99 Hz) , 2Н) 3.46-3.53 (m, 4Н) 1.28-1.36 (m, 3H) 1.13 (s, 6H).

3) ethyl 1-hydroxy-3H-[1,3]dioxolo[4,5-g][2,1]benzoxaborole-7-carboxylate

- 57 042660

NaBH4 (20 mg, 0.54 mmol) was added in portions to a solution of ethyl 4-(5,5-dimethyl-1,3,2dioxaborinan-2-yl)-5-formyl-1,3-benzodioxol-2-carboxylate (360 mg, 1.08 mmol) in MeOH (10 ml) at 0°C under N2. The mixture was then stirred for 30 minutes. The reaction was quenched with H2O and adjusted to pH=1 with HCl (6N), extracted with EtOAc and the combined organic phase washed with brine. The organic layer was dried over anhydrous Na ₂ SO ₄ , filtered and concentrated. The residue was triturated with MTBE to give ethyl 1-hydroxy-3H-[1,3]dioxolo[4,5-g][2,1]benzoxaborole-7carboxylate (200 mg, 60%) as a yellow solid.

¹ H NMR: DMSO 400 MHz δ 9.23 (s, 1H) 7.12 (d, J=7.91 Hz, 1H) 6.89 (d, J=7.91 Hz, 1H) 6.66 (s, 1H) 4.93 (s, 2H) 4.24 ( q, J=7.07 Hz, 2H) 1.24 (t, J=7.09 Hz, 3H)

4) 1-hydroxy-3H-[1,3]dioxolo[4,5-g][2,1]benzoxaborole-7-carboxylic acid

LiOH (96 mg, 4 mmol) was added in portions to a solution of ethyl 1-hydroxy-3H-[1,3]dioxolo[4.5g][2,1]benzoxaborole-7-carboxylate (500 mg, 2 mmol) in THF ( 6 ml)/H ₂ O (2 ml) at 20°C under N2. The mixture was then stirred for 2 hours. The reaction was quenched by adding H ₂ O, extracted with EtOAc. The aqueous phase was adjusted to pH=1 with HCl (6N), extracted with EtOAc and the combined organic phases washed with brine, dried and concentrated. The residue was triturated with MTBE to give 1-hydroxy3H-[1,3]dioxolo[4,5-g][2,1]benzoxaborole-7-carboxylic acid (200 mg, 40%) as a yellow solid.

1H NMR: DMSO 400 MHz δ 9.22 (s, 1H) 7.09 (d, J=7.72 Hz, 1H) 6.87 (d, J=7.94 Hz, 1H) 6.54 (s, 1H) 4.93 (s, 2H).

5) methyl 5-formyl-4-hydroxy-2,3-dihydrobenzofuran-2-carboxylate H ₃ CO ^OH \u003d ^C - D (w ^he

To a mixture of methyl 4-hydroxy-2,3-dihydrobenzofuran-2-carboxylate (CAS 403619-67-0) (1.94 g, 10 mmol), para-formaldehyde (660 mg, 22 mmol) and MgCl ₂ (1.9 g, 20 mmol) in THF (50 mL) was added dropwise with Et ₃ N (2.02 g, 20 mmol) at 20°C under N2. The mixture was then stirred for 3 hours at 85°C. The reaction was quenched with H2O, extracted with EtOAc and the combined organic phase was washed with brine. The organic layer was dried over anhydrous Na ₂ SO ₄ , filtered and concentrated. The residue was purified on a column to give methyl 5-formyl-4-hydroxy-2,3-dihydrobenzofuran-2-carboxylate (1 g, 50%) as a yellow solid.

¹ H NMR: CDCl ₃ 400 MHz δ 11.45 (s, 1H) 9.66-9.74 (m, 1H) 7.40 (d, J=8.41 Hz, 1H) 6.59 (d, J=8.41 Hz, 1H) 5.35 (dd, J =10.73, 6.59 Hz, 1H) 3.76-3.86 (m, 3H) 3.54 (dd, J=16.06, 10.79 Hz, 1H) 3.35 (dd, J=16.00, 6.46 Hz, 1H).

6) methyl 7-chloro-5-formyl-4-hydroxy-2,3-dihydrobenzofuran-2-carboxylate

Sulfuryl chloride (32.5 g, 60 mmol), MeOH (7.7 g, 24 mmol) in DCM (140 ml) was added dropwise 24 mmol) at 0°C. The mixture was stirred at 0° C. for 16 hours. The reaction was quenched with H ₂ O and extracted with EtOAc. The combined organic layers were washed with brine. dried and concentrated. The crude product was triturated with MTBE to give methyl 7-chloro-5-formyl-4-hydroxy-2,3-dihydrobenzofuran-2-carboxylate (6.4 g, 41%) as a yellow solid.

1H NMR: CDCl3 400 MHz δ 9.65-9.71 (m, 1H) 7.42 (s, 1H) 5.43 (dd, J=10.69, 6.50 Hz, 1H) 3.82-3.89 (m, 3H) 3.61 (dd, J=16.10, 10.80 Hz, 1H) 3.37-3.49 (m, 1H).

- 58 042660

7) methyl-7-chloro-5-formyl-4-(trifluoromethylsulfonyloxy)-2,3-dihydrobenzofuran-2-carboxylate

To a solution of methyl 7-chloro-5-formyl-4-hydroxy-2,3-dihydrobenzofuran-2-carboxylate (6.4 g, 25 mmol) and Et ₃ N (10.1 g, 100 mmol) in DCM (70 ml) dropwise trifluoromethanesulfonic acid anhydride (10.6 g, 37.5 mmol) was added at 0°C. The mixture was stirred at 0°C for 2 h. The reaction was quenched with H2O and extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The crude product was purified on a column (PE:EtOAc=100:1~20:1) to give methyl 7-chloro-5formyl-4-(trifluoromethylsulfonyloxy)-2,3-dihydrobenzofuran-2-carboxylate (5g, 52%) in form of a yellow solid.

1H NMR: CDCl3 400 MHz δ 10.04 (s, 1H) 7.90 (s, 1H) 5.49 (dd, J=10.58, 6.17 Hz, 1H) 3.87 (s, 3H) 3.793.85 (m, 1H) 3.62-3.71 (m, 1H).

8) methyl-7-chloro-4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-formyl-2,3-dihydrobenzofuran-2carboxylate

A mixture of methyl 7-chloro-5-formyl-4-(trifluoromethylsulfonyloxy)-2,3-dihydrobenzofuran-2carboxylate (6 g, 15.46 mmol), 2-(5,5-dimethyl-1,3,2-dioxaborinan-2- yl)-5,5-dimethyl-1,3,2dioxaborinan (10.48 g, 46.38 mmol), KOAc (9.1 g, 92.76 mmol) and Pd(dppf)Cl ₂ in dioxane (60 ml) were stirred at 90°C for 1 h. The reaction was quenched with H2O and extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The crude product was purified on a column (PE:EtOAc=50:1~10:1) to give methyl 7-chloro-4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-formyl2 ,3-dihydrobenzofuran-2-carboxylate (4 g, 74%) as a yellow solid.

1H NMR: CDCl ₃ 400 MHz δ 10.04 (s, 1H) 7.74 (s, 1H) 5.36 (dd, J=10.80, 6.84 Hz, 1H) 3.83 (s, 3H) 3.80 (s, 4H) 3.70-3.78 (m , 1H) 3.51–3.58 (m, 1H) 1.11 (br s, 1H) 1.09 (s, 5H).

9) methyl 5-chloro-1-hydroxy-3-methyl-7,8-dihydro-3H-furo[2,3-g][2,1]benzoxαborol-7-carboxylate

To a solution of methyl 7-chloro-4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-formyl-2,3dihydrobenzofuran-2-carboxylate (5 g, 14.2 mmol) in THF ( 60 ml), methylmagnesium bromide (9.5 ml, 28.4 mmol, 3 M) was added dropwise at 0°C under N2. The mixture was stirred at 20° C. for 16 hours. HCl (4 ml, 6N) was added to the reaction mixture. The reaction was quenched with H ₂ O and extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The crude product was purified by preparative HPLC (TFA), CH3CN-H2O) to give methyl 5-chloro-1-hydroxy-3-methyl-7,8-dihydro-3H-furo[2,3-g][2,1]benzoxaborole-7 -carboxylate (409 mg, 10%) as a yellow solid.

1H NMR: CDCl ₃ 400 MHz δ 7.09 (s, 1H) 5.35 (dd, J=10.58, 6.39 Hz, 1H) 5.25 (qd, J=6.54, 2.43 Hz, 1H) 3.82 (d, J=1.32 Hz, 3 H) 3.70-3.79 (m, 1H) 3.53-3.61 (m, 1H) 1.48 (dd, J=6.50, 2.09 Hz, 3H).

Compounds 2-3 listed below in table. 3 was prepared by analogy with example 1 mentioned above.

- 59 042660

Compound ^{R1 R2 RJ R4 R5 R6} A-CO ₂ R ⁶ MC m/z (M+l)/ MC retention time LNMR(DMSO)/CAS number 2 H H n n n n -O-CH(CO ₂ R ⁶ )-O- 223 3 H n n n n CH ₂ CH ₃ -O-CH(CO ₂ R ⁶ )-O- 251 4 H n n n n CH ₃ -O-CH(CO ₂ R ⁶ )-O- 237 5 H n n n n SNz -O-CH(CO ₂ R ⁶ )-CH ₂ - 235 6 H n n n n H -O-CH(CO ₂ R ⁶ )-CH ₂ - 221 7 H n n C1 n SNz -O-CH(CO ₂ R ⁶ )-CH ₂ - enantiomer 1 269 8 H n n C1 n SNz -O-CH(CO ₂ R ⁶ )-CH ₂ - enantiomer 2 269 9 CH ₃ n n C1 n SNz -O-CH(CO ₂ R ⁶ )-CH ₂ - 283 10 H n n F n SNz -OC(CO ₂ R ⁶ )-CH- 251 eleven H n n F n H -OC(CO ₂ R ⁶ )-CH- 237 12 H n n F n SNz -O-CH(CO ₂ R ⁶ )-CH ₂ - 253 13 H n n F n H -O-CH(CO ₂ R ⁶ )-CH ₂ - 239 14 H n n n n SNz -CH ₂ -CH(CO ₂ R ⁶ )-CH ₂ - 233 15 H n n n n CH ₂ CH ₃ -O-CH(CO ₂ R ^b )-CH ₂ -O- 265 16 H n n n n CH ₂ CH ₃ -O-CH ₂ -CH(CO ₂ R ⁶ )- 0- 265 17 H n n n n SNz -CH ₂ -CH(CO ₂ R ⁶ )- 0- 235 18 H n n n n H -CH ₂ -CH(CO ₂ R ⁶ )- 0- 221 19 H n n _CF3 n SNz -CH ₂ -CH(CO ₂ R ⁶ )-CH ₂ - 301 20 H n n n n SNz -CH ₂ -CH(CO ₂ R ⁶ )-CH ₂ -CH ₂ - 247 21 H n n n n H -CH ₂ -CH(CO ₂ R ⁶ )-CH ₂ -CH ₂ - 233 22 H n n _CF3 n H -CH ₂ -CH(CO ₂ R ⁶ )-CH ₂ - 287 23 n n n n n SNz -S-CH(CO ₂ R ^b )-CH ₂ - 251 24 n n n n n H -S-CH(CO ₂ R ⁶ )-CH ₂ - 237 25 n n n n n CH ₂ CH ₃ -O-CH(CO ₂ R ⁶ )-CH ₂ - 249 26 n n n n n CH ₂ CCH -O-CH(CO ₂ R ⁶ )-CH ₂ - 259 27 n n n n n ch ₂ cf ₃ -O-CH(CO ₂ R ^b )-CH ₂ - 303 28 n n n n n CH ₂ CH ₂ DOS ₃ -O-CH(CO ₂ R ^b )-CH ₂ - 279 29 n n n n n SNz -OC(CH3)(CO ₂ R ⁶ )-CH ₂ - 249 thirty n n n n n from ₆ to ₅ -O-CH(CO ₂ R ⁶ )-CH ₂ - 297

B. Application examples.

The herbicidal activity of the azines of formula (I) was demonstrated in the following greenhouse experiments.

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

For pre-emergence treatments, active ingredients that have been suspended or emulsified in water are applied directly after seeding using fine spray nozzles. The containers were gently watered to promote germination and growth and then covered with clear plastic lids until the plants were established. This coating promoted uniform germination of the test plants, provided that it was not impaired by the active ingredients.

For post-emergence treatment, the test plants were first grown to a height of 3 to 8 cm, depending on the characteristics of the plant, and only then treated with active ingredients that were suspended or emulsified in water. For this purpose, the test plants were 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 before treatment.

Depending on the species, the plants were kept at 10-25°C or 20-35°C, respectively.

The test period lasted from 2 to 4 weeks. During this time, the plants were cared for and their response to individual treatments was evaluated.

The evaluation was carried out using a scale from 0 to 100. 100 means no plant appearance or complete destruction of at least ground fragments, and 0 means no damage or normal natural growth. At values of at least 60 herbicidal activity is said to be moderate, at values of at least 70 herbicidal activity is said to be good, and at values of at least 85 herbicidal activity is said to be very good.

The plants used in the greenhouse experiments were of the following species.

- 60 042660

bayer code scientific name ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AMARE Amaranthus retroflexus AVEFA Avena fatua ECHCG Echinocloa crus-galli POLCO Polygonum convolvulus SEBEX Sesbania exaltata SETVI Setaria viridis SETFA Setaria fab eri

The results of the herbicidal activity of the compounds I against various types of weeds and some monocot plants of crops at various application rates are shown in examples 1-9 below.

Example 1

At a rate of 2 kg/ha, Compound 2, which was applied post-emergence, showed 100%, 90% and 80% herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Setaria viridis, respectively.

Example 2

At a rate of 2 kg/ha, compound 3, which was applied post-emergence, showed 100 and 100% herbicidal activity against Amaranthus retroflexus and Setaria viridis, respectively.

Example 3

At a rate of 2 kg/ha, Compound 4, which was applied post-emergence, showed 100 and 100% herbicidal activity against Amaranthus retroflexus and Abutilon theophrasti, respectively.

Example 4

At a rate of 2 kg/ha, Compound 5 applied post-emergence showed 100, 100 and 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria viridis, respectively, and pre-emergence showed 95, 80 and 85% herbicidal activity. herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Setaria faberi, respectively.

Example 5

At a rate of 2 kg/ha, Compound 6, which was applied post-emergence, showed 100, 100 and 98% herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Alopecurus myosuroides, respectively, and pre-emergence showed 80% herbicidal activity against Amaranthus retroflexus.

Example 6

At a rate of 2 kg/ha, compound 7, which was applied post-emergence, showed 100%, 100% and 100% herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Avena fatua, respectively.

Example 7

At a rate of 2 kg/ha, compound 8, which was applied post-emergence, showed 100, 100 and 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria viridis, respectively, and pre-emergence showed 80% herbicidal activity against Setaria faberi .

Example 8

At a rate of 2 kg/ha, Compound 9 applied post-emergence showed 100%, 100% and 98% herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Avena fatua, respectively.

Example 9

At a rate of 0.25 kg/ha, compound 12 applied post-emergence showed 100, 95 and 100% herbicidal activity against Sesbania exaltata, Polygonum convolvulus and Amaranthus retroflexus, respectively.

Example 10

At a rate of 0.25 kg/ha, compound 13 applied post-emergence showed 100%, 85% and 100% herbicidal activity against Sesbania exaltata, Polygonum convolvulus and Amaranthus retroflexus, respectively.

Example 11.

At a rate of 0.25 kg/ha, compound 14 applied post-emergence showed 100% herbicidal activity against Abutilon theophrasti, Sesbania exaltata and Amaranthus retroflexus.

Example 12.

At a rate of 2 kg/ha, compound 15 applied post-emergence showed 90% herbicidal activity against Abutilon theophrasti and Amaranthus retroflexus.

-

Claims (14)

Example 13. At a rate of 2 kg/ha, compound 16, which was applied post-emergence, showed 100% herbicidal activity against Amaranthus retroflexus. Example 14 At a rate of 2 kg/ha, compound 17 applied post-emergence showed 100% herbicidal activity against Amaranthus retroflexus. Example 15 At a rate of 1 kg/ha, compound 18, which was applied post-emergence, showed 100 and 90% herbicidal activity against Amaranthus retroflexus and Setaria viridis, respectively. Example 16 At a rate of 1 kg/ha, compound 19, which was applied post-emergence, showed 100, 100 and 90% herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Setaria viridis. respectively. Example 17. At a rate of 1 kg/ha, compound 20 applied post-emergence showed 100% herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Setaria viridis. Example 18. At a rate of 1 kg/ha, compound 21 applied post-emergence showed 100%, 80% and 80% herbicidal activity against Amaranthus retroflexus, Setaria viridis and Alopecurus myosuroides, respectively. Example 19. At a rate of 1 kg/ha, compound 22 applied post-emergence showed 100%, 100% and 95% herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Alopecurus myosuroides, respectively. CLAIM 1. Use of a compound of formula (I) wherein A is a fused saturated or unsaturated 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members; R ¹ is selected from the group consisting of H and C ₁ -C ₆ alkyl; R ² is selected from the group consisting of H and C ₁ -C ₆ alkyl; R ³ is selected from the group consisting of H, halo, OH, CN, amino, NO2, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ - alkoxy, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkoxy, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy) -C ₃ -C ₆ -alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or fully halogenated; R ⁴ is selected from the group consisting of H, halogen, OH, CN, amino, NO2, C ₁ -C6 alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkoxy , C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkoxy, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -αkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or completely halogenated; R ⁵ is selected from the group consisting of H, halogen, OH, CN, amino, NO2, C ₁ -C6 alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, C ₁ -C ₆ alkoxy , C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ -alkoxy, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or completely halogenated; R ⁶ is selected from the group consisting of H, C ₁ -C ₆ alkyl, C ₃ -C ₆ alkenyl, C 3 -C ₆ alkynyl, (C ₁ -C 6 alkoxy)-C ₁ -C ₆ alkyl, (C ₁ -C ₆ -alkoxy)-C ₃ -C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy) -C ₃ -C ₆ -alkynyl, phenyl, phenylC ₁ -C ₆ -alkyl, where the aliphatic and phenyl parts of the above radicals are unsubstituted, partially or fully halogenated; or its agriculturally acceptable salts, to control unwanted vegetation. 2. Use according to claim 1, wherein A is a fused saturated 5- or 6-membered heterocycle having one or two O atoms as a ring member. - 62 042660 3. Use according to claim 1, wherein A is a fused unsaturated 5- or 6-membered heterocycle having one or two O atoms as ring members. 4. Use according to claim 1, wherein A is a fused saturated 5- or 6-membered carbocycle. 5. Use according to claim 1, wherein A is a fused unsaturated 5- or 6-membered carbocycle. 6. Use according to any one of the preceding claims, wherein R ¹ and R ² are independently selected from the group consisting of H and C 1 -C ₄ -alkyl, in particular both are H. 7. Use according to any one of the preceding claims, wherein R ³ is selected from the group consisting of H, halogen, C _g C ₆ alkyl and C 1 -C ₆ haloalkyl, in particular H, C 1 and F. 8. Use according to any one of the preceding claims, wherein R ⁴ is selected from the group consisting of H, halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, in particular H, CF ₃ , CH ₃ , C1 and F. 9. Use according to any one of the preceding claims, wherein R ⁵ is selected from the group consisting of H, halo, C1- _C6 alkyl and C1- _C6 haloalkyl, in particular H, C1 and F. 10. Use according to any one of the preceding claims, wherein R ⁶ is selected from the group consisting of H and C1-C ₆ alkyl, in particular H, CH ₃ and CH ₂ CH ₃ . 11. Use according to any of the preceding claims, wherein R ⁶ is H or CH ₃ and R ⁴ is selected from the group consisting of halogen, Ci-C6 alkyl and CpC6 haloalkyl, in particular C1 and F. 12. Compound of formula (I) wherein A is a fused saturated or unsaturated 4-7 membered carbocycle or a fused saturated or unsaturated 4-7 membered heterocycle having 1, 2 or 3 heteroatoms selected from O or S as ring members; R ¹ is selected from the group consisting of H and C1-C ₆ alkyl; R ² is selected from the group consisting of H and C1-C ₆ alkyl; R ³ is selected from the group consisting of H, halogen, OH, CN, amino, NO ₂ , Ci-Cb-alkyl, C ₃ -Cb-alkenyl, C ₃ -Cb-alkynyl, CpCb-alkoxy, C ₂ -Cb- alkenyloxy, C ₂ -Cb-alkynyloxy, (C1-Cb-alkoxy) -C1-Cb-alkyl, (C1-Cb-alkoxy) -C1-C ₆ -alkoxy, (C1-Cb-alkoxy) -C ₃ -C ₆ -alkenyl, (C1-Cb-alkoxy)-C ₃ -C ₆ alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or fully halogenated; R ⁴ is selected from the group consisting of H, halogen, OH, CN, amino, NO ₂ , C1-C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -Cb alkynyl, CpCb alkoxy, C ₂ - Cb-alkenyloxy, C ₂ -Cb-alkynyloxy, (C1-Cb-alkoxy) -C1-Cb-alkyl, (C1-Cb-alkoxy) -C1-Cb-alkoxy, (C1-Cb-alkoxy) -C ₃ - Cb-alkenyl, (C1-Cb-alkoxy)-C ₃ -Cb-alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or fully halogenated; R ⁵ is selected from the group consisting of H, halo, OH, CN, amino, NO ₂ , CpCb-alkyl, C ₃ -Cb-alkenyl, C ₃ -Cb-alkynyl, Ci-Cb-alkoxy, C ₂ -Cb-alkenyloxy, C ₂ -Cbalkynyloxy, (C1-Cb-alkoxy) -C1-Cb-alkyl, (C1-Cb-alkoxy)-C1-Cb-alkoxy, (C1-Cb-alkoxy)-C ₃ -Sbalkenyl, (C1-C ₆ -alkoxy)-C ₃ -C ₆ -alkynyl, where the aliphatic parts of the above radicals are unsubstituted, partially or fully halogenated; R ⁶ is selected from the group consisting of H, C1-C ₆ alkyl, C ₃ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, (Ci-C ₆ alkoxy)-C1-C6-alkyl, (C1- Cb-alkoxy)-C ₃ -Cb-alkenyl, (C1-Cb-alkoxy)-C ₃ -Cb-alkynyl, phenyl, phenylCi-Cb-alkyl, where the aliphatic and phenyl parts of the above radicals are unsubstituted, partially or completely halogenated; or its agriculturally acceptable salts, provided that if A is cyclohexane, R ¹ , R ² , R ³ and R ⁴ are H, R ⁶ is not H or CH ₃ . 13. A herbicidal composition comprising a herbicidally active amount of at least one compound as defined in any one of claims 1 to 11 and at least one inert liquid and/or solid carrier. 14. A method of controlling unwanted vegetation, which comprises providing a herbicidally effective amount of at least one compound of formula (I) or an agriculturally acceptable salt thereof, as defined in any one of claims 1 to 11, to affect plants, their seeds and/or their place of origin. Eurasian Patent Organization, EAPO Russia, 109012, Moscow, Maly Cherkassky per., 2