EA044989B1 - DIAMINOTRIAZINE COMPOUNDS - Google Patents

Description

The present invention relates to diaminotriazine compounds and their use as herbicides. The present invention also relates to agrochemical compositions for the protection of cultivated plants and a method for controlling unwanted vegetation.

Diaminotriazines and their use as herbicides are known, for example, from WO 2015/155272 and WO 2015/162166.

However, there is still room for improvement, for example, regarding the activity, measure of activity and compatibility with beneficial plants of the known herbicidal compounds.

It is therefore an object of the present invention to provide compounds having improved herbicidal activity, in particular good herbicidal activity at low application rates. Moreover, herbicides must be sufficiently compatible with crops for commercial application.

These and other objects are achieved by the diaminotriazine compounds of formula (I) defined below and their salts suitable for agricultural use.

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

where q represents 0, 1, 2 or 3;

Q represents O;

where R ^a is selected from the group consisting of halogen, CN, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, where parts of the radicals are unsubstituted, partially or completely halogenated;

R ^b is selected from the group consisting of halogen, CN, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, where parts of the radicals are unsubstituted, partially or completely halogenated;

for q = 2 or 3 it is possible that R ^b are the same or different;

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

R ² is selected from the group consisting of H, halogen, OH, CN, C ₁ -C ₆ -alkyl, (C ₁ -C ₆ -alkoxy)-C ₁ -C ₆ alkyl, C ₃ -C ₆ -cycloalkyl, ( C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₄ -alkyl, C ₁ -C ₆ -alkoxy, C ₂ -C ₆ -alkenyloxy, C2-C6alkynyloxy, C ₃ -C ₆ -cycloalkoxy, (C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₄ -alkoxy, where the aliphatic and cycloaliphatic parts of the radicals are unsubstituted, partially or completely halogenated;

R ³ is selected from the group consisting of H, halogen, CN, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -haloalkyl, C 1 -C 6 -alkoxy and C ₁ -C ₆ -haloalkoxy;

R ⁴ is selected from the group consisting of halogen, CN, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl, C ₃ -C ₆ -cycloalkyl, (C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkenyl and C ₁ -C ₆ -alkoxy-C ₁ -C ₆ alkyl, where the aliphatic and cycloaliphatic parts of the radicals are unsubstituted, partially or completely halogenated; or

R ³ and R ⁴ together with the carbon atom to which they are attached form a substituent selected from the group consisting of carbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, and substituent >C=CR ^x R ^y , where R ^x and R ^y represent hydrogen, C 1 -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl, C ₃ -C ₆ -cycloalkyl or CR ^x R ^y forms a 3-6 membered cycloalkyl;

R ⁵ is selected from the group consisting of H, C ₁ -C ₆ -alkyl;

R ⁶ is phenyl which is unsubstituted or carries 1, 2, 3, 4 or 5 R ^6A radicals which are selected from the group consisting of halogen, OH, CN, amino, NO2, C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C2-C6 alkynyl, C ₁ -C ₆ -αalkoxy, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, (C ₁ -C ₆ -alkoxy) -C ₁ -C ₆ - alkyl, (C1-C6alkoxy)-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, C1-C6alkylthio, (C ₁ -C ₆ -alkyl)sulfinyl, (C ₁ -C ₆ -alkyl)sulfonyl, (C ₁ -C ₆ -alkyl)amino, di(C ₁ -C ₆ -alkyl)amino , (C ₁ -C ₆ -alkyl)carbonyl, (C ₁ -C ₆ -alkoxy)carbonyl, (C ₁ -C ₆ -alkyl)carbonyloxy, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkoxy, (C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₄ -alkyl, (C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₄ -alkoxy, where the aliphatic and cycloaliphatic parts of the radicals are unsubstituted, partially or completely halogenated, and where the cycloaliphatic moieties of the radicals may carry 1, 2, 3, 4, 5 or 6 methyl groups, it is possible that the R ^6A are the same or different;

R ⁷ and R ⁷ are independently selected from the group consisting of hydrogen, halogen, C ₁ -C ₄ -alkyl, C 2 -C 6 -alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ - haloalkoxy, C ₃ -C ₆ -cycloalkyl;

including its agriculturally acceptable salts.

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The present invention also relates to herbicidal compositions containing at least one diaminotriazine compound of formula (I) and at least one inert liquid and/or solid carrier, and at least one surfactant.

Additional embodiments of the present invention are obvious from the claims, description and examples. It should be understood that the features of the subject matter of the invention mentioned above and not yet illustrated below can be used not only in the combination given in each particular case, but also in other combinations without departing from the scope of the invention.

As used herein, the terms control and control are synonymous.

As used herein, the terms unwanted vegetation, unwanted growth, unwanted plants and noxious 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 diaminotriazine compounds of formula (I) as described herein are capable of forming geometric isomers, for example E/Z isomers, the invention concerns both pure isomers and mixtures thereof. Likewise, the invention concerns the use of pure isomers, and the use of mixtures thereof, and compositions containing pure isomers or mixtures thereof.

If the diaminotriazine 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 covers both pure enantiomers or diastereomers and mixtures thereof. Likewise, the invention relates to the use of pure enantiomers or diastereomers, and the use of mixtures thereof, and compositions containing pure enantiomers or diastereomers or mixtures thereof.

If the diaminotriazine 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, as a rule, are salts of those cations and acid addition salts of those acids whose cations and anions, respectively, do not have a harmful effect on 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, as well as ammonium and substituted ammonium, which has from one to four hydrogen atoms replaced by _C1 -C4-alkyl, hydroxy- _C1- C4-alkyl, C1- _C4 - _alkoxyC1 -C4-alkyl, hydroxy-C1 _- C4-alkoxy- _C1- C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (digly colamine salt), di(2-hydroxyethyl-1-yl) ammonium (diolamine salt), tris-(2-hydroxyethyl) ammonium (trolamine salt), tris-(2-hydroxypropyl) ammonium, benzyltrimethylammonium, benzyltriethylammonium, K, K, K-trimethylethanolammonium (choline salt) and, in addition, phosphonium ions, sulfonium ions, preferably tri(C ₁ -C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(C ₁ -C4-alkyl)sulfonium, and finally salts of polybasic amines such as K,K-bis-(3-aminopropyl)methylamine and diethylenetriamine.

The anions of suitable acid addition salts are mainly chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, as well as C ₁ -C4 alkane anions acids, preferably formate, acetate, propionate and butyrate.

Additional embodiments of the present invention are apparent from the claims, description and examples. It should be understood that the features mentioned above and the objects of the invention shown below can be used not only in the combination shown in each individual case, but also in other combinations, without departing from the scope of the invention.

Organic moieties mentioned in the definition of variables, for example, Q, q, R ^a , R ^b , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁷ , are - similar to the term halogen - collective terms for separate lists of representatives of individual groups. The term halogen means in each case fluorine, chlorine, bromine or iodine. All hydrocarbon chains, that is, all alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulphonyl, (alkyl)amino, di(alkyl)amino chains may be straight or branched, the prefix C _n -Cm meaning in each case possible number of carbon atoms in a group. The same applies to complex radicals such as cycloalkylalkyl and phenylalkyl.

Examples of such values are:

C ₁ -C ₄ -alkyl, as well as C ₁ -C ₄ -alkyl substituents C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C1-C4 -alkylsulfonyl, (C ₁ -C ₄ -alkyl)carbonyl, ( C ₁ -C ₄ -alkyl)carbonyl, (C ₁ -C ₄ -alkoxy)carbonyl, (Ci-C ₄ alkyl)carbonyloxy, C ₁ -C ₄ -alkyloxy-C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl, (C1-C4-alkylamino)carbonyl, di(C ₁ - _{C 4} -alkyl)aminocarbonyl, (C ₁ -C ₄ -alkylamino)sulfonyl, di(C1-C ₄ alkyl) aminosulfonyl or phenyl-C1-C ₄ -alkyl: for example, CH3, C ₂ H ₅ , n-propyl, CH(CH ₃ ) ₂ , n-butyl,

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CH(CH3)-C2H ₅ , CH2-CH(CH3)2 and C(CH3)3;

C1-Cb-alkyl, as well as CgC^alkyl substituents _C1 - _C6 -alkoxy, _C1 - _C6 -alkylthio, _C1 - _C6 alkylsulfonyl, (C1- _C6 -alkyl)carbonyl, (C1- _C6 -alkyl)carbonyl, (C1- _C6 -alkoxy)carbonyl, (C1-C6alkyl)carbonyloxy, _C1 - _C6 -alkyloxy- _C1 - _C6 -alkyl, _C3 - _C6- cycloalkyl- _C1 -C ₆ -alkyl, phenyl(C ₁ -C ₆ alkyl)aminocarbonyl, (C ₁ -C ₆ -alkylamino)carbonyl, di(C ₁ -C ₆ -alkyl)aminocarbonyl, (C1-C ₆ alkylamino)sulfonyl, di(C ₁ -C ₆ -alkyl)aminosulfonyl or phenyl-C ₁ -C ₆ -alkyl: C ₁ -C ₄ -alkyl, as mentioned above, as well as, 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 -Cb-alkenyl, as well as C ₂ -Cb-alkenyl substituents (C ₁ -C ₆ -alkoxy)-C2-C ₆ -alkenyl: linear or branched ethyl unsaturated hydrocarbon group having 2-6 carbon atoms and C=Double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 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-2propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3 -hexenyl, 4-hexenyl, 5hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2pentenyl, 2-methyl -2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3pentenyl, 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, as well as C ₂ -C ₆ -alkynyl substituent (C ₁ -C ₆ -alkoxy)-C ₂ -C ₆ -alkynyl: linear or branched unsaturated hydrocarbon group having from 2 to 6 carbon atoms and 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 etc.;

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

C3-C6-cycloalkyl: monocyclic saturated hydrocarbons having from 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C ₁ -C ₄ -alkoxy: for example, methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2methylpropoxy and 1,1-dimethylethoxy;

C ₁ -C ₆ -alkoxy, as well as C ₁ -C ₆ -alkoxy substituents (C ₁ -C ₆ -alkoxy)carbonyl, (C ₁ -C ₆ alkoxy)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, as well as, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxybutoxy, 1,1-dimethylpropoxy, 1,2dimethylpropoxy , 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-metallenetoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2dimethylbutoxy , 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy ;

C1-C4 haloalkoxy: C1-C4 alkoxy radical as mentioned above, which is partially or completely substituted with 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- 3 044989 chloro-2-fluoroethoxy, 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,

3-chloropropoxy, 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;

C1- _C6 -haloalkoxy: _C1 - _C4 -alkoxy, as mentioned above: _C1 - _C4 -haloalkoxy, 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 ₂ -C6 alkenyloxy: C ₂ -C ₆ alkenyl, as defined above, which is attached via an oxygen atom, such as ethenyloxy (vinyloxy), 1-propenyloxy, 2-propenyloxy (allyloxy), 1-butenyloxy, 2-butenyloxy, 3 -butenyloxy 1-methyl-2-propenyloxy, etc.;

C ₂ -C ₆ -alkynyloxy: C ₂ -C ₆ -alkynyl, as defined above, which is attached via 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 ₄ -alkylthio: for example, methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;

C ₁ -C ₆ -alkylthio: C ₁ -C ₄ -alkylthio, as mentioned above, and also, for example, pentylthio, 1methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1 ,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2dimethylbutylthio, 2 ,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio;

C ₁ -C ₆ -alkylsulfinyl (C ₁ -C ₆ -alkyl-S(=O)-): for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1- dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3 -methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1, 2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl;

C ₁ -C ₆ -alkylsulfonyl (C ₁ -C ₆ -alkyl-S(O) ₂ -): for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1- dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3- methylpentylsulfonyl, 4- methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2- trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1ethyl-2-methylpropylsulfonyl;

(C ₁ -C ₄ -alkyl)amino, as well as (C ₁ -C ₄ -alkylamino) (C ₁ -C ₄ -alkylamino)carbonyl or (C ₁ -C ₄ -alkylamino)sulfonyl substituents: for example, methylamino, ethylamino , propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino or 1,1-dimethylethylamino;

(C ₁ -C ₆ -alkyl)amino, as well as (C ₁ -C ₆ -alkylamino) substituents (C ₁ -C ₆ -alkylamino)carbonyl, phenyl (C ₁ -C ₆ -alkyl)aminocarbonyl or (C ₁ - C ₆ -alkylamino)sulfonyl: (C ₁ -C ₄ -alkyl)amino, as mentioned above, and also, for example, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino , 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3dimethylbutylamino, 2,2-dimethylbutylamino, 2,3 -dimethylbutyl-amino 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1methylpropylamino or 1-ethyl-2-methylpropylamino;

di(C ₁ -C ₄ -alkyl)amino, as well as di(C ₁ -C ₄ -alkylamino) di(C ₁ -C ₄ -alkylamino)carbonyl or di(C ₁ -C ₄ -alkylamino)sulfonyl substituents: for example , N,N-dimethylαamino, N,N-diethylamino, N,N-di(1methylethyl)amino, K,K-dipropylamino, N,N-dibutylamino, K,K-di(1-methylpropyl)amino, N,N -di(2methylpropyl)amino, N,N-di(1,1-dimethylethyl)αamino, K-ethyl-K-methylamino, K-methyl-K-propylamino, K-methyl-K-(1-methylethyl)amino, K-butyl-K-methylamino, K-methyl-K-(1-methylpropyl)amino, K-methyl-K(2-methylpropyl)amino, K-(1,1-dimethylethyl)-K-methylamino, K-ethyl -K-propylamino, K-ethyl-K-(1methylethyl)amino, K-butyl-K-ethylamino, K-ethyl-K-(1-methylpropyl)amino, K-ethyl-K-(2methylpropyl)amino, K- ethyl-K-(1,1-dimethylethyl)amino, K-(1-methylethyl)-K-propylamino, K-butyl-K- 4 044989 propylamino, K-(1-methylpropyl)-K-propylamino, K-( 2-methylpropyl)-K-propylamino, N-(1,1dimethylethyl)-K-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino , N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, Nbutyl-N-(1-methylpropyl)amino, N- butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1 - dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1dimethylethyl)-N-(2-methylpropyl)amino;

di(C ₁ -C ₆ -alkylamino)amino, as well as di(C ₁ -C ₆ -alkylamino) substituents of di(C ₁ -C ₆ -alkylamino)carbonyl or di(C ₁ -C ₆ -alkylamino)sulfonyl: di (C1-C ₄ -alkyl)amino, as mentioned above, and also, for example, N-methyl-N-pentylamino, N-methyl-N-(1-methylbutyl)amino, N-methyl-N-(2-methylbutyl )amino, N-methylN-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1-ethylpropyl)amino, Nmethyl-N-hexylamino, N- methyl-N-(1,1-dimethylpropyl)amino, N-methyl-N-(1,2-dimethylpropyl)amino, Nmethyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methylpentyl) amino, N-methyl-N-(3-methylpentyl)amino, N-methyl-N-(4-methylpentyl)amino, N-methyl-N-(1,1-dimethylbutyl)amino, N-methyl-N-( 1,2-dimethylbutyl)amino, N-methyl-N-(1,3-dimethylbutyl)amino, N-methyl-N-(2,2-dimethylbutyl)amino, N-methyl-N(2,3-dimethylbutyl) amino, N-methyl-N-(3,3-dimethylbutyl)αmino, N-methyl-N-(1-ethylbutyl)amino, Nmethyl-N-(2-ethylbutyl)amino, N-methyl-N-(1, 1,2-trimethylpropyl)amino, N-methyl-N-(1,2,2-trimethylpropyl)amino, N-methyl-N-(1 -ethyl-1-methylpropyl)amino, N -methyl-N-(1 -ethyl-2-methylpropyl)amino, N-ethylN-pentylamino, N-ethyl-N-(1-methylbutyl)amino, N-ethyl-N-(2-methylbutyl)amino, N-ethyl-N-(3methylbutyl) amino, N-ethyl-N-(2,2-dimethylpropyl)amino, N-ethyl-N-(1-ethylpropyl)amino, N-ethyl-Nhexylamino, N-ethyl-N-(1,1-dimethylpropyl)amino , N-ethyl-N-(1,2-dimethylpropyl)amino, N-ethyl-N-(1methylpentyl)amino, N-ethyl-N-(2-methylpentyl)amino, N-ethyl-N-(3-methylpentyl) )amino, N-ethyl-N-(4methylpentyl)amino, N-ethyl-N-(1,1-dimethylbutyl)amino, N-ethyl-N-(1,2-dimethylbutyl)amino, N-ethyl-N( 1,3-dimethylbutyl)amino, N-ethyl-N-(2,2-dimethylbutyl)amino, N-ethyl-N-(2,3-dimethylbutyl)amino, Nethyl-N-(3,3-dimethylbutyl)amino , N-ethyl-N-(1-ethylbutyl)amino, N-ethyl-N-(2-ethylbutyl)amino, N-ethylN-(1,1,2-trimethylpropyl)amino, N-ethyl-N-(l ,2,2-trimethylpropyl)amino, N-ethyl-N-(1-ethyl-1-methylpropyl)amino, N-ethyl-N-(1-ethyl-2-methylpropyl)amino, N-propyl-N-pentylamino , N-butyl-N-pentylamino, N,N-dipentylamino, N-propyl-N-hexylamino, N-butyl-N-hexylamino, N-pentyl-N-hexylamino or N,N-dihexylamino;

C ₃ -C ₆ -cycloalkyl, as well as C ₃ -C ₆ -cycloalkyl substituents (C ₃ -C ₆ -cycloalkyl)carbonyl, (C ₃ -C ₆ cycloalkyl) -C ₁ -C ₆ -alkyl, (C ₃ - C ₆ -cycloalkyl)carbonyl and (C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₆ -alkoxy: cycloaliphatic radical having from 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C ₃ -C ₆ -cycloalkoxy: a cycloaliphatic radical having from 3 to 6 carbon atoms and attached via an oxygen atom, such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy and cyclohexyloxy;

(C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₆ -alkyl: C ₁ -C ₆ -alkyl, in particular C ₁ -C ₄ -alkyl as defined above, such as methyl or ethyl, where 1 hydrogen atom replaced by C ₃ -C ₆ -cycloalkyl as defined above, examples include cyclopropylmethyl (CH ₂ -cyclopropyl), cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropylethyl (CH( _CH3 )cyclopropyl), 1-cyclobutylethyl, 1-cyclopentylethyl, 1cyclohexylethyl, 2-cyclopropylethyl (CH ₂ CH ₂ -cyclopropyl), 2-cyclobutylethyl, 2-cyclopentylethyl or 2-cyclohexylethyl;

(C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₆ -alkoxy: C ₁ -C ₆ -alkoxy, in particular C ₁ -C ₄ -αalkoxy as defined above, such as methoxy or ethoxy, where 1 hydrogen atom replaced by _C3 - _C6 -cycloalkyl as defined above, examples include cyclopropylmethoxy ( _OCH2 -cyclopropyl), cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, 1-cyclopropylethoxy (O-CH( _CH3 )cyclopropyl), 1-cyclobutylethoxy, 1cyclopentylethoxy, 1 -cyclohexylethoxy, 2-cyclopropylethoxy (OCH ₂ CH ₂ cyclopropyl), 2-cyclobutylethoxy, 2-cyclopentylethoxy and 2-cyclohexylethoxy;

(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, such as methyl, ethyl or isopropyl, where 1 hydrogen atom 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, 2-methoxypropyl, 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, such as methoxy or ethoxy, where 1 atom hydrogen is replaced by C ₁ -C ₆ -alkoxy as defined above, examples include methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, butoxymethoxy, 2-methoxyethoxy, 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, such as 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, such as ethynyl, propynyl or 2-butynyl, where 1 hydrogen atom is replaced by C ₁ -C ₆ -alkoxy, as defined above;

- 5 044989 (C1-Cb-alkyl)carbonyl: C1-Cb-alkyl, as mentioned above, which is attached to the rest of the molecule through a carbonyl group;

(C ₁ -C ₆ -alkoxy)carbonyl: C ₁ -C ₆ -alkyloxy, as mentioned above, which is attached to the remainder of the molecule through a carbonyl group;

(C ₁ -C ₆ -alkylamino)carbonyl: (C ₁ -C ₆ -alkyl)amino, as mentioned above, which is attached to the remainder of the molecule through a carbonyl group;

(C ₁ -C ₆ -alkylamino)sulfonyl: (C ₁ -C ₆ -alkyl)amino, as mentioned above, which is attached to the remainder of the molecule through a sulfonyl group;

di(C ₁ -C6-alkylamino)carbonyl: di(C ₁ -C6-alkyl)amino, as mentioned above, which is attached to the remainder of the molecule through a carbonyl group;

di(C ₁ -C ₆ -alkylamino)sulfonyl: di(C ₁ -C ₆ -alkyl)amino, as mentioned above, which is attached to the remainder of the molecule through a sulfonyl group;

phenyl-C ₁ -C ₆ -alkyl: C ₁ -C ₆ -alkyl, in particular C ₁ -C ₄ -alkyl as defined above, such as methyl 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.;

3-6 membered heterocyclyl: a monocyclic saturated or partially unsaturated hydrocarbon having from three to six ring members as mentioned above, which, in addition to carbon atoms, contains one or two heteroatoms selected from O, S and N; for example, saturated heterocycles such as 2-oxiranyl, 2-oxetanyl, 3-oxetanyl, 2-aziridinyl, 3-thietanyl, 1-azetidinyl, 2azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2- thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,4-dithian-2-yl, 1,3-dithian-5-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-he xahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-6-yl, 2-morpholinyl, 3morpholinyl or 4-morpholinyl, for example 2H-pyran-2-yl, 2H- pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4- yl, 2H-thiopyran-5-yl, 2Hthiopyran-6-yl;

partially saturated heterocycles, such as 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2yl, 2,4-dihydrothien-3-yl, 4,5-dihydropyrrol-2-yl, 4,5-dihydropyrrol-3- yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 4,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-3yl, 4,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-4-yl, 4,5dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-5-yl, 2, 3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol- 4-yl, 2,3-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-2- yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3dihydroimidazol-2-yl, 2,3- dihydroimidazol-3-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol- 5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4- yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 2,3-dihydrothiazol-3- yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl, 3,4-dihydrothiazol-5-yl, 3,4-dihydrothiazol-2-yl, 3,4dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl, 3,6-dihydro-2H-pyran-2-yl, 3,6-dihydro-2H- pyran-3-yl, 3,6-dihydro-2H-pyran-4-yl, 3,6-dihydro-2H-pyran-5-yl, 3,6-dihydro-2H-pyran-6-yl, 3, 4-dihydro-2Hpyran-3-yl, 3,4-dihydro-2H-pyran-4-yl, 3,4-dihydro-2H-pyran-6-yl, 5,6-dihydro-4H-1,3- oxazin-2-yl;

5- and 6-membered heteroaryl which contains 1, 2 or 3 heteroatoms selected from O, S and N;

A 5-membered or 6-membered heteroaromatic radical which, in addition to carbon atoms, contains 1, 2 or 3 heteroatoms as ring members selected from O, S and N, for example 1, 2 or 3 nitrogen atoms or 1 oxygen atom or sulfur and optionally 1 or 2 nitrogen atoms:

in particular: a five-membered monocyclic heteroaryl which contains from one to three heteroatoms selected from O, S and N.

For example, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4- oxazolyl, 5-oxazolyl, 2-thiazolyl, 4thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2- silt, etc.;

- 6 044989

A 6-membered monocyclic heteroaryl that contains from one to three nitrogen atoms as ring members:

e.g. 2-pyridinyl (2-pyridyl), 3-pyridinyl (3-pyridyl), 4-pyridinyl (4-pyridyl), 1-oxopyridin-2-yl, 1-oxopyridin-3-yl, 1-oxopyridin-4-yl , 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl and 1,2,3-triazinyl, 1,2,4-triazinyl and 1,3,5triazinyl.

The preferred embodiments of the invention mentioned herein below are to be understood as being preferred either independently of each other or in combination with each other. Specific groups of embodiments of the invention relate to those diaminotriazines of formula (I) wherein the variables are Q, q, m, R ^a , R ^b , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁷ independently of each other or in combination with each other have the following meanings.

Specific groups of embodiments relate to diaminotriazine compounds of formula (I), wherein Q is as defined above. In particular, Q represents O.

Additional specific groups of embodiments relate to diaminotriazine compounds of formula (I), wherein R ^a is as defined above.

In particular

R ^a is selected from the group consisting of halogen, CN, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, where parts of the radicals are unsubstituted, partially or completely halogenated.

Even more preferably, R ^a is selected from F, Cl.

Additional specific groups of embodiments relate to diaminotriazine compounds of formula (I), wherein R ^b is as defined above.

In particular

R ^b is selected from the group consisting of halogen, CN, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, where parts of the radicals are unsubstituted, partially or completely halogenated;

for q = 2 or 3 it is possible that R ^b are the same or different.

Even more preferable

R ^b is selected from F, Cl, Br, methyl.

Additional specific groups of embodiments relate to diaminotriazine compounds of formula (I), wherein R ¹ represents H.

Additional specific groups of embodiments relate to diaminotriazine compounds of formula (I), wherein R ² is selected from the group consisting of hydrogen, fluorine, C ₁ -C ₄ -alkyl and C1C ₄ -alkoxy.

Additional specific group (1) of embodiments relate to diaminotriazine compounds of formula (I), where R ³ is selected from the group consisting of hydrogen, fluorine, C ₁ -C ₄ -alkyl, Ci-C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy and C ₁ -C ₆ -haloalkoxy.

In groups (1) of embodiments, R ⁴ is as defined above.

Preferably R ⁴ is selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl and C1-C6 alkoxy-C1 -C6-alkyl. Additional specific group (2) of embodiments relate to diaminotriazine compounds of formula (I), wherein R ³ and R ⁴ together with the carbon atom to which they are attached form a substituent selected from the group consisting of C3-C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkenyl.

Particularly preferred examples of CR ² R ³ R ⁴ are radicals in which R ² , R ³ and R ⁴ are as shown in lines 1-64 of the table. 1a.

- 7 044989

Table la

No. R ² R ³ R ⁴ 1. Η СНз СНз 2. F F СНз 3. F N СНз 4. F СНз СНз 5. СНз СНз СНз 6. F N С2Н5 7. H СНз С2Н5 8. F СНз С2Н5 9. H OSNZ СНз 10. H OSNZ С2Н5 AND. F С2Н5 С2Н5 12. H OSNZ С2Н5 13. H N CH(CHz) ₂ 14. H F CH(CHz) ₂ 15. F F CH(CHz) ₂ 16. H СНз CH(CHz) ₂ 17. H OSNZ CH(CHz) ₂ 18. F СНз СН(СНз)г 19. H N CH2CH2CH3 20. H F CH2CH2CH3 21. F F CH2CH2CH3 22. H СНз CH2CH2CH3 23. H OSNZ CH2CH2CH3 24. F СНз CH2CH2CH3 25. H N С(СНз)з 26. H F С(СНз)з 27. F F С(СНз)з 28. H СНз С(СНз)з 29. H OSNZ С(СНз)з thirty. F СНз С(СНз)з 31. H N Cyclopropyl 32. H F Cyclopropyl 33. F F Cyclopropyl 34. H СНз Cyclopropyl 35. H OSNZ Cyclopropyl 36. F СНз Cyclopropyl 37. H СНз CF3 38. F СНз CF3 39. H CH2-CH2 40. СНз CH2-CH2 41. OSNZ CH2-CH2 42. F CH2-CH2 43. Cl CH2-CH2 44. H CH2-CH2-CH2 45. СНз CH2-CH2-CH2 46. OSNZ CH2-CH2-CH2 47. F CH2-CH2-CH2 48. Cl CH2-CH2-CH2 49. H CH2-CH2-CH2-CH2 50. СНз CH2-CH2-CH2-CH2 51. OSNZ CH2-CH2-CH2-CH2 52. F CH2-CH2-CH2-CH2 53. Cl CH2-CH2-CH2-CH2 54. H CH2-CH2-CH2-CH2-CH2 55. СНз CH2-CH2-CH2-CH2-CH2 56. OSNZ CH2-CH2-CH2-CH2-CH2 57. F CH2-CH2-CH2-CH2-CH2 58. Cl CH2-CH2-CH2-CH2-CH2 59. H O-CH2-CH2-CH2 60. СНз O-CH2-CH2-CH2 61. OSNZ O-CH2-CH2-CH2 62. Η O-CH2-CH2-CH2-CH2 63. СНз O-CH2-CH2-CH2-CH2 64. OSNZ O-CH2-CH2-CH2-CH2

-8044989

R ⁵ represents H.

Additional specific groups of embodiments relate to diaminotriazine compounds of formula (I), wherein R ⁶ is phenyl, which is unsubstituted or carries 1, 2, 3, 4 or 5 R ^6A radicals, which are selected from the group consisting of halogen, OH, CN, amino, NO ₂ , C ₁ -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -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 ₂ -C ₆ -alkenyl, (C ₁ -C ₆ -alkoxy)-C ₂ -C ₆ -alkynyl, QC ₆ alkylthio, (C ₁ -C ₆ -alkyl)sulfinyl, (C ₁ -C ₆ -alkyl)sulfonyl, (C ₁ -C ₆ -alkyl)amino, di(C ₁ -C ₆ alkyl)amino, (C1-C ₆ -alkyl)carbonyl, (C1-C ₆ -alkoxy)carbonyl, (C1-C ₆ -alkyl)carbonyloxy, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ -cycloalkoxy, (C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₄ -alkyl, (C ₃ -C ₆ -cycloalkyl)-C ₁ -C ₄ -alkoxy, where the aliphatic and cycloaliphatic moieties of the radicals are unsubstituted, partially or completely halogenated and where the cycloaliphatic moieties of the radicals may bear 1, 2, 3, 4, 5 or 6 methyl groups, it is possible that the R ^6A are the same or different.

Particularly preferred examples for R ⁶ are those given in lines 1-148 of the table. 2a.

_______________________ ____________Table 2a

No. R ⁶ 1. SbN ₅ 2. 2-FC ₆ H ₄

No. R ⁶ 3. 3-F-C6H4 4. 4-F-C6H4

- 9 044989

5. 2-S1-SbN ₄ 6. 3-S1-SbN ₄ 7. 4-S1-SbN ₄ 8. 2-Vg-SbN ₄ 9. 3-Vg-SbN ₄ 10. 4-Vg-SbN ₄ AND. 2-1-SbN ₄ 12. 3-1-SbN ₄ 13. 4-1-SbN ₄ 14. 2-CN-C ₆ H ₄ 15. 3-CN-C ₆ H ₄ 16. 4-CN-C ₆ H ₄ 17. 2-OSNz-SbN ₄ 18. 3-OSNz-SbN ₄ 19. 4-OSН3-С ₆ Н ₄ 20. 2-СНз-СБН ₄ 21. 3-SNz-SbN ₄ 22. 4-SNz-SbN ₄ 23. 2-CH ₂ -CHZ-SbN ₄ 24. 3-CH ₂ -CHZ-SbN ₄ 25. 4-CH ₂ -CHZ-SbN ₄ 26. 2,3-Rg-SbNz 27. 2,4-Pr-SbNz 28. 2.5-Rg-SbNz 29. 2,6-Rg-SbNz thirty. 3,4-P ₂ -SbNz 31. 3.5-Rg-SbNz 32. 2,3-С1 ₂ -СбНз 33. 2,4-С1 ₂ -СбНз 34. 2.5-C1 ₂ -SbNz 35. 2.6-C1 ₂ -SbNz 36. 3,4-С1г-СбНз 37. 3.5-S1g-SbNz 38. 2-Р-3-С1-СбНз 39. 2-Р-4-С1-СбНз 40. 2-Р-5-С1-СбНз 41. 2-Р-6-С1-СбНз 42. 3-Р-2-С1-СбНз 43. 3-Р-4-С1-СбНз 44. 3-Р-5-С1-СбНз 45. 3-Р-6-С1-СбНз 46. 4-Р-2-С1-СбНз 47. 4-Р-3-С1-СбНз 48. 4-Р-5-С1-СбНз 49. 4-Р-6-С1-СбНз 50. 2-R-Z-OSNz-SbNz 51. 2-R-4-OSNz-SbNz 52. 2-R-5-OSNz-SbNz

53. 2-R-6-OSNz-SbNz 54. Z-R-2-OSNz-SbNz 55. 2-S1-3-R-SbNz 56. 2-S1-4-R-SbNz 57. 2-S1-5-R-SbNz 58. 2-S1-6-R-SbNz 59. 3-S1-2-R-SbNz 60. 3-S1-4-R-SbNz 61. 3-S1-5-R-SbNz 62. 3-S1-6-R-SbNz 63. 4-S1-2-R-SbNz 64. 4-S1-3-R-SbNz 65. 4-S1-5-R-SbNz 66. 4-S1-6-R-SbNz 67. 2-S1-3-OSNz-SbNz 68. 2-S1-4-OSNz-SbNz 69. 2-S1-5-OSNz-SbNz 70. 2-S1-6-OSNz-SbNz 71. 3-S1-2-OSNz-SbNz 72. 3-S1-4-OSNz-SbNz 73. 3-S1-5-OSNz-SbNz 74. 3-S1-6-OSNz-SbNz 75. 4-S1-2-OSNz-SbNz 76. 4-S1-3-OSNz-SbNz 77. 4-S1-5-OSNz-SbNz 78. 4-S1-6-OSNz-SbNz 79. 2,3,4-Rz-SbNg 80. 2,3,5-Rz-SbNg 81. 2,3,6-Rz-SbN ₂ 82. 2,4,5-Rz-SbNg 83. 2,4,6-Rz-SbNg 84. 3,4,5 -Rz-SbN ₂ 85. 2,3,4-С1з-Сн ₂ 86. 2,3,5-S1z-SbN ₂ 87. 2,3,6-S13-SbN ₂ 88. 2,4,5-С1з-Сн ₂ 89. 2,4,6-С1з-Сн ₂ 90. 3,4,5-С1з-Сн ₂ 91. ABOUT. 92. /GA 93. Cl

- 10 044989

94. Cl 95. JTA H ₃ c^ _s >- 96. _H3Cbs 97. CH ₃ 6- 98. O- 99. ·? Cl 100. Cl b- 101. Cl b- 102. b- CH ₃ 103. _H3Cb- 104. CH ₃ b- 105. b- 106. c^- 107. Cl

108. Cl 109. Fl H ₃ C^o>- 110. _H3Cb- 111. CH ₃ 112. FROM. O 114. Cl b- 115. Cl 116. °?CH ₃ 117. _H3Cb- 118. CH ₃ b- 119. π—N Q- 120. H ₃ C H. s

- 11 044989

Additional specific groups of embodiments relate to diaminotriazine compounds of formula (I), wherein R ⁷ and R ⁷ are selected from the group consisting of hydrogen, halogen, C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ -alkynyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₃ -C ₆ -cycloalkyl, preferably H and F.

Preference is given to diaminotriazine compounds of formula (Ia), which correspond to diaminotriazines of formula (I) wherein R ¹ and R ² are hydrogen, Q is O, R ^a is F, R ⁴ is CH3 and R ^b1 , R ^b2 , R ^b3 , R ⁶ , R ⁷ , R ⁷ are independently as defined in paragraph 1 or, preferably, as defined below

- 12 044989

Specific embodiments of compounds I are the following compounds: IA, IB, IC, ID, I-E, IF. In these formulas, substituents where R ¹ and R ² represent hydrogen, Q represent O, R ^a represent F, R ⁴ represent CH3, R7 R ⁷ represent H, H or F, F and R ^b1 , R ^b2 , R ^b 3 and R ⁶ are as defined in the paragraphs in Table A

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Table 1-1. Compounds of formula IA, IB, IC, ID, I-E, IF, IG, IH, II, IJ, in which the values for the combination of R ^b1 , R ^b2 , R ^b3 and R ⁶ for each individual compound correspond in each case to one of rows of the table A (connections IA. 1-1.A-1- IA.1-1.A-384, IB.1-1.A-1- IB.1-1.A-384, IC.1-1A-1 - IC.11.A-384, ID.1-1.A-1- ID.1-1.A-384, 1-E.1-1.A-1- IE.1-1.A-384 , IF.1-1.A-1- IF.1-1.A-384, IG.1-1.A-1- IG.1-1.A-384, IH.1-1.A-1 -IH.1-1.A-384, II.1-1.A-1- II.1-1.A-384, IJ.1-1.A-1- IJ.1-1.A-384 ).

- 14 044989

Table A

No. R.M. R ^b2 R ^b3 R ⁶ A-1 N N N phenyl A-2 F N N phenyl A-3 C1 n n phenyl A-4 Vg n n phenyl A-5 N F n phenyl A-6 F F n phenyl A-7 C1 F n phenyl A-8 Vg F n phenyl A-9 N N F phenyl A-10 F N F phenyl A-11 C1 N F phenyl A-12 Vg N F phenyl A-13 N F F phenyl A-14 F F F phenyl A-15 C1 F F phenyl A-16 Vg F F phenyl A-17 N N C1 phenyl A-18 F N C1 phenyl A-19 C1 N C1 phenyl A-20 Vg N C1 phenyl A-21 N F C1 phenyl A-22 F F C1 phenyl A-23 C1 F C1 phenyl A-24 Vg F C1 phenyl A-25 N N n 2-fluorophenyl A-26 F N n 2-fluorophenyl

- 15 044989

A-27 Cl H H 2-fluorophenyl A-28 Br H H 2-fluorophenyl A-29 H F H 2-fluorophenyl A-30 F F H 2-fluorophenyl A-31 Cl F H 2-fluorophenyl A-32 Br F H 2-fluorophenyl A-33 H H F 2-fluorophenyl A-34 F H F 2-fluorophenyl A-35 Cl H F 2-fluorophenyl A-36 Br H F 2-fluorophenyl A-37 H F F 2-fluorophenyl A-38 F F F 2-fluorophenyl A-39 Cl F F 2-fluorophenyl A-40 Br F F 2-fluorophenyl A-41 H H Cl 2-fluorophenyl A-42 F H Cl 2-fluorophenyl A-43 Cl H Cl 2-fluorophenyl A-44 Br H Cl 2-fluorophenyl A-45 H F Cl 2-fluorophenyl A-46 F F Cl 2-fluorophenyl A-47 Cl F Cl 2-fluorophenyl A-48 Br F Cl 2-fluorophenyl A-49 H H H 3-fluorophenyl, A-50 F H H 3-fluorophenyl, A-51 Cl H H 3-fluorophenyl, A-52 Br H H 3-fluorophenyl, A-53 H F H 3-fluorophenyl, A-54 F F H 3-fluorophenyl, A-55 Cl F H 3-fluorophenyl, A-56 Br F H 3-fluorophenyl, A-57 H H F 3-fluorophenyl, A-58 F H F 3-fluorophenyl, A-59 Cl H F 3-fluorophenyl, A-60 Br H F 3-fluorophenyl,

- 16 044989

A-61 H F F 3-fluorophenyl, A-62 F F F 3-fluorophenyl, A-63 Cl F F 3-fluorophenyl, A-64 Br F F 3-fluorophenyl, A-65 H H Cl 3-fluorophenyl, A-66 F H Cl 3-fluorophenyl, A-67 Cl H Cl 3-fluorophenyl, A-68 Br H Cl 3-fluorophenyl, A-69 H F Cl 3-fluorophenyl, A-70 F F Cl 3-fluorophenyl, A-71 Cl F Cl 3-fluorophenyl, A-72 Br F Cl 3-fluorophenyl, A-73 H H H 2-chlorophenyl A-74 F H H 2-chlorophenyl A-75 Cl H H 2-chlorophenyl A-76 Br H H 2-chlorophenyl A-77 H F H 2-chlorophenyl A-78 F F H 2-chlorophenyl A-79 Cl F H 2-chlorophenyl A-80 Br F H 2-chlorophenyl A-81 H H F 2-chlorophenyl A-82 F H F 2-chlorophenyl A-83 Cl H F 2-chlorophenyl A-84 Br H F 2-chlorophenyl A-85 H F F 2-chlorophenyl A-86 F F F 2-chlorophenyl A-87 Cl F F 2-chlorophenyl A-88 Br F F 2-chlorophenyl A-89 H H Cl 2-chlorophenyl A-90 F H Cl 2-chlorophenyl A-91 Cl H Cl 2-chlorophenyl A-92 Br H Cl 2-chlorophenyl A-93 H F Cl 2-chlorophenyl A-94 F F Cl 2-chlorophenyl

- 17 044989

A-95 Cl F Cl 2-chlorophenyl A-96 Br F Cl 2-chlorophenyl A-97 H H H 3-chlorophenyl A-98 F H H 3-chlorophenyl A-99 Cl H H 3-chlorophenyl A-100 Br H H 3-chlorophenyl A-101 H F H 3-chlorophenyl A-102 F F H 3-chlorophenyl A-103 Cl F H 3-chlorophenyl A-104 Br F H 3-chlorophenyl A-105 H H F 3-chlorophenyl A-106 F H F 3-chlorophenyl A-107 Cl H F 3-chlorophenyl A-108 Br H F 3-chlorophenyl A-109 H F F 3-chlorophenyl A-110 F F F 3-chlorophenyl A-lll Cl F F 3-chlorophenyl A-112 Br F F 3-chlorophenyl A-113 H H Cl 3-chlorophenyl A-114 F H Cl 3-chlorophenyl A-115 Cl H Cl 3-chlorophenyl A-116 Br H Cl 3-chlorophenyl A-117 H F Cl 3-chlorophenyl A-118 F F Cl 3-chlorophenyl A-119 Cl F Cl 3-chlorophenyl A-120 Br F Cl 3-chlorophenyl A-121 H H H 2,6-difluorophenyl A-122 F H H 2,6-difluorophenyl A-123 Cl H H 2,6-difluorophenyl A-124 Br H H 2,6-difluorophenyl A-125 H F H 2,6-difluorophenyl A-126 F F H 2,6-difluorophenyl A-127 Cl F H 2,6-difluorophenyl A-128 Br F H 2,6-difluorophenyl

- 18 044989

A-129 H H F 2,6-difluorophenyl A-130 F H F 2,6-difluorophenyl A-131 Cl H F 2,6-difluorophenyl A-132 Br H F 2,6-difluorophenyl A-133 H F F 2,6-difluorophenyl A-134 F F F 2,6-difluorophenyl A-135 Cl F F 2,6-difluorophenyl A-136 Br F F 2,6-difluorophenyl A-137 H H Cl 2,6-difluorophenyl A-138 F H Cl 2,6-difluorophenyl A-139 Cl H Cl 2,6-difluorophenyl A-140 Br H Cl 2,6-difluorophenyl A-141 H F Cl 2,6-difluorophenyl A-142 F F Cl 2,6-difluorophenyl A-143 Cl F Cl 2,6-difluorophenyl A-144 Br F Cl 2,6-difluorophenyl A-145 H H H 2,6-dichlorophenyl A-146 F H H 2,6-dichlorophenyl A-147 Cl H H 2,6-dichlorophenyl A-148 Br H H 2,6-dichlorophenyl A-149 H F H 2,6-dichlorophenyl A-150 F F H 2,6-dichlorophenyl A-151 Cl F H 2,6-dichlorophenyl A-152 Br F H 2,6-dichlorophenyl A-153 H H F 2,6-dichlorophenyl A-154 F H F 2,6-dichlorophenyl A-155 Cl H F 2,6-dichlorophenyl A-156 Br H F 2,6-dichlorophenyl A-157 H F F 2,6-dichlorophenyl A-158 F F F 2,6-dichlorophenyl A-159 Cl F F 2,6-dichlorophenyl A-160 Br F F 2,6-dichlorophenyl A-161 H H Cl 2,6-dichlorophenyl A-162 F H Cl 2,6-dichlorophenyl

- 19 044989

A-163 Cl H Cl 2,6-dichlorophenyl A-164 Br H Cl 2,6-dichlorophenyl A-165 H F Cl 2,6-dichlorophenyl A-166 F F Cl 2,6-dichlorophenyl A-167 Cl F Cl 2,6-dichlorophenyl A-168 Br F Cl 2,6-dichlorophenyl A-169 H H H 2-chloro-6-fluorophenyl A-170 F H H 2-chloro-6-fluorophenyl A-171 Cl H H 2-chloro-6-fluorophenyl A-172 Br H H 2-chloro-6-fluorophenyl A-173 H F H 2-chloro-6-fluorophenyl A-174 F F H 2-chloro-6-fluorophenyl A-175 Cl F H 2-chloro-6-fluorophenyl A-176 Br F H 2-chloro-6-fluorophenyl A-177 H H F 2-chloro-6-fluorophenyl A-178 F H F 2-chloro-6-fluorophenyl A-179 Cl H F 2-chloro-6-fluorophenyl A-180 Br H F 2-chloro-6-fluorophenyl A-181 H F F 2-chloro-6-fluorophenyl A-182 F F F 2-chloro-6-fluorophenyl A-183 Cl F F 2-chloro-6-fluorophenyl A-184 Br F F 2-chloro-6-fluorophenyl A-185 H H Cl 2-chloro-6-fluorophenyl A-186 F H Cl 2-chloro-6-fluorophenyl A-187 Cl H Cl 2-chloro-6-fluorophenyl A-188 Br H Cl 2-chloro-6-fluorophenyl A-189 H F Cl 2-chloro-6-fluorophenyl A-190 F F Cl 2-chloro-6-fluorophenyl A-191 Cl F Cl 2-chloro-6-fluorophenyl A-192 Br F Cl 2-chloro-6-fluorophenyl A-193 H H H 2-methoxyphenyl A-194 F H H 2-methoxyphenyl A-195 Cl H H 2-methoxyphenyl A-196 Br H H 2-methoxyphenyl

- 20 044989

A-197 H F H 2-methoxyphenyl A-198 F F H 2-methoxyphenyl A-199 Cl F H 2-methoxyphenyl A-200 Br F H 2-methoxyphenyl A-201 H H F 2-methoxyphenyl A-202 F H F 2-methoxyphenyl A-203 Cl H F 2-methoxyphenyl A-204 Br H F 2-methoxyphenyl A-205 H F F 2-methoxyphenyl A-206 F F F 2-methoxyphenyl A-207 Cl F F 2-methoxyphenyl A-208 Br F F 2-methoxyphenyl A-209 H H Cl 2-methoxyphenyl A-210 F H Cl 2-methoxyphenyl A-211 Cl H Cl 2-methoxyphenyl A-212 Br H Cl 2-methoxyphenyl A-213 H F Cl 2-methoxyphenyl A-214 F F Cl 2-methoxyphenyl A-215 Cl F Cl 2-methoxyphenyl A-216 Br F Cl 2-methoxyphenyl A-217 H H H 3-methoxyphenyl A-218 F H H 3-methoxyphenyl A-219 Cl H H 3-methoxyphenyl A-220 Br H H 3-methoxyphenyl A-221 H F H 3-methoxyphenyl A-222 F F H 3-methoxyphenyl A-223 Cl F H 3-methoxyphenyl A-224 Br F H 3-methoxyphenyl A-225 H H F 3-methoxyphenyl A-226 F H F 3-methoxyphenyl A-227 Cl H F 3-methoxyphenyl A-228 Br H F 3-methoxyenyl A-229 H F F 3-methoxyenyl A-230 F F F 3-methoxyenyl

- 21 044989

A-231 Cl F F 3-methoxyphenyl A-232 Br F F 3-methoxyphenyl A-233 H H Cl 3-methoxyphenyl A-234 F H Cl 3-methoxyphenyl A-235 Cl H Cl 3-methoxyphenyl A-236 Br H Cl 3-methoxyphenyl A-237 H F Cl 3-methoxyphenyl A-238 F F Cl 3-methoxyphenyl A-239 Cl F Cl 3-methoxyphenyl A-240 Br F Cl 3-methoxyphenyl A-241 H H H 4-methoxyphenyl A-242 F H H 4-methoxyphenyl A-243 Cl H H 4-methoxyphenyl A-244 Br H H 4-methoxyphenyl A-245 H F H 4-methoxyenyl A-246 F F H 4-methoxyenyl A-247 Cl F H 4-methoxyenyl A-248 Br F H 4-methoxyenyl A-249 H H F 4-methoxyenyl A-250 F H F 4-methoxyenyl A-251 Cl H F 4-methoxyenyl A-252 Br H F 4-methoxyenyl A-253 H F F 4-methoxyenyl A-254 F F F 4-methoxyenyl A-255 Cl F F 4-methoxyenyl A-256 Br F F 4-methoxyenyl A-257 H H Cl 4-methoxyenyl A-258 F H Cl 4-methoxyenyl A-259 Cl H Cl 4-methoxyenyl A-260 Br H Cl 4-methoxyenyl A-261 H F Cl 4-methoxyenyl A-262 F F Cl 4-methoxyenyl A-263 Cl F Cl 4-methoxyenyl A-264 Br F Cl 4-methoxyenyl

- 22 044989

A-265 H H H 2-methylphenyl A-266 F H H 2-methylphenyl A-267 Cl H H 2-methylphenyl A-268 Br H H 2-methylphenyl A-269 H F H 2-methylphenyl A-270 F F H 2-methylphenyl A-271 Cl F H 2-methylphenyl A-272 Br F H 2-methylphenyl A-273 H H F 2-methylphenyl A-274 F H F 2-methylphenyl A-275 Cl H F 2-methylphenyl A-276 Br H F 2-methylphenyl A-277 H F F 2-methylphenyl A-278 F F F 2-methylphenyl A-279 Cl F F 2-methylphenyl A-280 Br F F 2-methylphenyl A-281 H H Cl 2-methylphenyl A-282 F H Cl 2-methylphenyl A-283 Cl H Cl 2-methylphenyl A-284 Br H Cl 2-methylphenyl A-285 H F Cl 2-methylphenyl A-286 F F Cl 2-methylphenyl A-287 Cl F Cl 2-methylphenyl A-288 Br F Cl 2-methylphenyl A-289 H H H 3-methylphenyl A-290 F H H 3-methylphenyl A-291 Cl H H 3-methylphenyl A-292 Br H H 3-methylphenyl A-293 H F H 3-methylphenyl A-294 F F H 3-methylphenyl A-295 Cl F H 3-methylphenyl A-296 Br F H 3-methylphenyl A-297 H H F 3-methylphenyl A-298 F H F 3-methylphenyl

- 23 044989

A-299 Cl H F 3-methylphenyl A-300 Br H F 3-methylphenyl A-301 H F F 3-methylphenyl A-302 F F F 3-methylphenyl A-303 Cl F F 3-methylphenyl A-304 Br F F 3-methylphenyl A-305 H H Cl 3-methylphenyl A-306 F H Cl 3-methylphenyl A-307 Cl H Cl 3-methylphenyl A-308 Br H Cl 3-methylphenyl A-309 H F Cl 3-methylphenyl A-310 F F Cl 3-methylphenyl A-311 Cl F Cl 3-methylphenyl A-312 Br F Cl 3-methylphenyl A-313 H H H 4-methylphenyl A-314 F H H 4-methylphenyl A-315 Cl H H 4-methylphenyl A-316 Br H H 4-methylphenyl A-317 H F H 4-methylphenyl A-318 F F H 4-methylphenyl A-319 Cl F H 4-methylphenyl A-320 Br F H 4-methylphenyl A-321 H H F 4-methylphenyl A-322 F H F 4-methylphenyl A-323 Cl H F 4-methylphenyl A-324 Br H F 4-methylphenyl A-325 H F F 4-methylphenyl A-326 F F F 4-methylphenyl A-327 Cl F F 4-methylphenyl A-328 Br F F 4-methylphenyl A-329 H H Cl 4-methylphenyl A-330 F H Cl 4-methylphenyl A-331 Cl H Cl 4-methylphenyl A-332 Br H Cl 4-methylphenyl

- 24 044989

A-333 H F Cl 4-methylphenyl A-334 F F Cl 4-methylphenyl A-335 Cl F Cl 4-methylphenyl A-336 Br F Cl 4-methylphenyl A-337 H H H 2-thiophene A-338 F H H 2-thiophene A-339 Cl H H 2-thiophene A-340 Br H H 2-thiophene A-341 H F H 2-thiophene A-342 F F H 2-thiophene A-343 Cl F H 2-thiophene A-344 Br F H 2-thiophene A-345 H H F 2-thiophene A-346 F H F 2-thiophene A-347 Cl H F 2-thiophene A-348 Br H F 2-thiophene A-349 H F F 2-thiophene A-350 F F F 2-thiophene A-351 Cl F F 2-thiophene A-352 Br F F 2-thiophene A-353 H H Cl 2-thiophene A-354 F H Cl 2-thiophene A-355 Cl H Cl 2-thiophene A-356 Br H Cl 2-thiophene A-357 H F Cl 2-thiophene A-358 F F Cl 2-thiophene A-359 Cl F Cl 2-thiophene A-360 Br F Cl 2-thiophene A-361 H H H 3-thiophene A-362 F H H 3-thiophene A-363 Cl H H 3-thiophene A-364 Br H H 3-thiophene A-365 H F H 3-thiophene A-366 F F H 3-thiophene

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A-367 C1 F N 3-thiophene A-368 Vg F N 3-thiophene A-369 N N F 3-thiophene A-370 F N F 3-thiophene A-371 C1 N F 3-thiophene A-372 Vg N F 3-thiophene A-373 N F F 3-thiophene A-374 F F F 3-thiophene A-375 C1 F F 3-thiophene A-376 Vg F F 3-thiophene A-377 N N C1 3-thiophene A-378 F N C1 3-thiophene A-379 C1 N C1 3-thiophene A-380 Vg N C1 3-thiophene A-381 N F C1 3-thiophene A-382 F F C1 3-thiophene A-383 C1 F C1 3-thiophene A-384 Vg F C1 3-thiophene

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

Method A).

Azines of formula (I), where R ¹ represents H, C ₁ -C ₆ -alkyl, can be prepared by reacting halotriazines of formula (II) with amines of formula (III) in the presence of a base and/or catalyst, or in the presence of an acid as shown in the following diagram 1:

The variables Q, R ^a , R ^b , R ² , R ³ and R ⁴ , R ⁶ , R ⁷ and R ⁷ have particularly preferred meanings as in formula (I) mentioned above, and Hal is halogen ;

preferably Cl or Br;

particularly preferably Cl;

R ¹ represents H, C ₁ -C ₆ -alkyl;

particularly preferably R ¹ represents H; and R ⁵ represents H, C ₁ -C ₆ -alkyl;

also particularly preferably R ⁵ is H.

The reaction of halotriazines of formula (III) with an amine of formula (II) is usually carried out at a temperature of from 50°C to the boiling point of the reaction mixture, preferably from 50 to 150°C, especially preferably from 60 to 100°C, in an inert organic solvent (for example, P. Dao et al., Tetrahedron 2012, 68, 3856 - 3860). The reaction can be carried out at atmospheric pressure or hanging pressure, if appropriate, under an inert gas atmosphere, continuously or in batches. Halotriazines of formula (III) and compounds of formula (II) are used in equimolar amounts, or compounds of formula (II) are used in excess relative to the halotriazines of formula (III). Preferably, the molar ratio of the compound of formula (II) to halotriazines of formula (III) 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 halotriazines of formula (III) with compounds of formula (II) is carried out in an organic solvent.

Suitable solvents in principle are all which can dissolve halotriazines of formula (III) and amines of formula (II) at least partially and preferably completely under the reaction conditions.

- 26 044989

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 methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, also dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2imidazolidinone (DMI) , K,K-dimethylpropylene urea (DMUM), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (N-MP).

Preferred solvents are ethers as defined above. The term solvent, as used herein, also includes mixtures of two or more of the above compounds.

The reaction of halotriazines of formula (III) with compounds of formula (II) is carried out in the presence of a base or acid.

Examples of suitable bases include metal-containing bases and nitrogen-containing 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 oxide 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, formates, acetates of alkali and alkaline earth metals and salts of other metals with carboxylic acids such as sodium formate, sodium benzoate, lithium acetate, sodium acetate, acetate potassium, 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 bicarbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali 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 tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium; and, in addition, organic bases such as tertiary amines, such as tri-C ₁ -C ₆ -alkylamines, for example triethylamine, trimethylamine, N-ethyldiisopropylamine and Nmethylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N- methylmorpholine, as well as 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 alkali metal and alkaline earth metal alkoxides as defined above.

The term base, as used herein, 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 may be used in excess, preferably from 1 to 10, particularly preferably from 2 to 4 equivalents. bases relative to the halotriazines of formula (VI), and they can also be used as a solvent.

Examples of suitable acids are inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, p-toluenesulfonic acid; Lewis acids such as boron trifluoride, aluminum chloride, ferric chloride III, tin chloride IV, titanium chloride IV and zinc II chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid can also be used acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid.

Preferred bases are inorganic acids.

Acids are usually used in excess or, if appropriate, can be used as a solvent.

Completion of the reaction can be easily determined by one skilled in the art using conventional methods.

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 amines of formula (II) needed to prepare the compounds of formula (I) are commercially available or can be prepared by analogy with methods known in the literature (eg, Barnes et al., WO/2007/067612).

Halotriazines of formula (VI) necessary for the preparation of azines of formula (I), where R ⁵ represents H, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy-C ₁ -C ₆ -alkyl or C ₁ -C ₆ -alkoxy, known from the literature, commercially available and/or can be prepared by analogy (for example, JK Chakrabarti et al., Tetrahedron 1975,

31, 1879 - 1882) by reacting thiotriazines of formula (IV) with a source of halogen (eg Cl ₂ ) or other suitable halogenating agent (eg SOCl ₂ )

n n (IV) OY

The variables R ² , R ³ , and R ⁴ have meanings, particularly preferred meanings, as defined in formula (I) mentioned above; Hal is a halogen;

preferably Cl or Br;

particularly preferably Cl;

R* represents C ₁ -C ₆ -alkyl, C ₂ -C ₆ -haloalkyl or phenyl;

preferably C ₁ -C ₆ -alkyl or C ₂ -C ₆ -haloalkyl;

particularly preferably C ₁ -C ₆ alkyl;

particularly preferably CH ₃ ; And

R ⁵ represents H, C ₁ -C ₆ alkyl; more preferably hydrogen.

The reaction of thiotriazines of formula (IV) with a halogen (or halogenating agent) is usually carried out at a temperature of from 0°C to the boiling point of the reaction mixture, preferably from 15°C to the boiling temperature of the reaction mixture, especially preferably from 15 to 40°C, in an inert organic solvent (eg J.K. Chakrabarti et al., Tetrahedron 1975, 31, 1879 - 1882).

The reaction can be carried out at atmospheric pressure or hanging pressure, if appropriate, under an inert gas atmosphere, either continuously or in batches. In the method according to the invention, the halogen is used in excess relative to the thiotriazines of formula (IV).

The reaction of thiotriazines of formula (IV) with halogen is carried out in an organic solvent. Suitable solvents in principle are all which are capable of dissolving thiotriazines of formula (IV) and halogen 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, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform and carbon tetrachloride; ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol , as well as organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid, trifluoacetic acid.

Preferred solvents are halogenated hydrocarbons and organic acids as defined above.

The term solvent, as used herein, also includes mixtures of two or more of the above compounds.

Completion of the reaction can be easily determined by one skilled in the art using conventional methods.

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.

Thiotriazines of formula (IV) necessary for the preparation of halotriazines of formula (III) can be prepared by reacting the guanidine salt of formula (V) with carbonyl compounds of formula (VI) in the presence of a base

(V) (VI) (IV)

The variables R ² , R ³ and R ⁴ have values, in particular preferred values, as defined in formula (I) mentioned above;

R* is C ₁ -C ₆ alkyl, C ₂ -C ₆ haloalkyl or phenyl;

preferably C ₁ -C ₆ -alkyl or C ₂ -C ₆ -haloalkyl;

particularly preferably C ₁ -C ₆ alkyl;

particularly preferably CH ₃ ;

- 28 044989

L ¹ represents a nucleophilically replaceable leaving group such as halogen, CN, C 1 -C 6 alkoxy, C ₁ -C ₆ -alkylcarbonyloxy or C ₁ -C ₆ -alkoxycarbonyloxy;

preferably halogen or C ₁ -C ₆ -alkoxy;

particularly preferably Cl or C ₁ -C ₆ -alkoxy, also particularly preferably halogen;

particularly preferably Cl; And

L ² represents a nucleophilically replaceable leaving group such as halogen, C 1 -C 6 alkylsulfonyloxy, C ₁ -C ₆ haloalkylsulfonyloxy, C ₁ -C ₆ alkoxysulfonyloxy or phenylsulfonyloxy;

preferably halogen or C ₁ -C ₆ -haloalkylsulfonyloxy;

particularly preferably halogen;

particularly preferably I; And

R ⁵ represents H, C ₁ -C ₆ alkyl;

more preferably hydrogen.

The reaction of the guanidine salt of formula (V) with a carbonyl compound of formula (VI) is usually carried out at temperatures from 50°C to the boiling point of the reaction mixture, preferably from 50 to 100°C.

The reaction can be carried out at atmospheric pressure or hanging pressure, if appropriate, under an inert gas atmosphere, either continuously or in batches. In one embodiment of the method according to the invention, the guanidine salts of formula (V) and the carbonyl compound of formula (VI) are used in equimolar amounts.

In another embodiment of the method according to the invention, the carbonyl compound of formula (VI) is used in excess relative to the guanidine salts of formula (V). Preferably, the molar ratio of the carbonyl compound of formula (VI) to the guanidine salt of formula (V) is in the range of 1.5:1 to 1:1, preferably 1.2:1 to 1:1, particularly preferably 1.2:1, also particularly preferably 1:1. The reaction of a guanidine salt of formula (V) with a carbonyl compound of formula (VI) is usually carried out in an organic solvent.

Suitable solvents in principle are all which are capable of dissolving the guanidine salt of formula (V) and the carbonyl compound of formula (VI) at least partially and preferably completely under the reaction conditions.

Examples of suitable solvents are halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF) , nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N-dimethylpropylene urea (DMUM), dimethyl sulfoxide (DMSO) and 1-methyl-2-pyrrolidinone (NMP).

Preferred solvents are ethers and dipolar aprotic solvents as defined above.

More preferably, the solvents are ethers as defined above.

The term solvent, as used herein, also includes mixtures of two or more of the above compounds.

The reaction of guanidine salts of formula (V) with a carbonyl compound of formula (VI) is carried out in the presence of a base.

Examples of suitable bases include metal-containing bases and nitrogen-containing bases.

Examples of suitable metal-containing bases are inorganic compounds such as alkali metal oxide 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 and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate and calcium carbonate, as well as alkali metal bicarbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali and alkaline earth metal phosphates such as sodium phosphate, potassium phosphate and calcium phosphate; and, in addition, organic bases such as tertiary amines, such as tri-C ₁ C ₆ -alkylamines, for example triethylamine, trimethylamine, N-ethyl-diisopropylamine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine, as well as 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 tri-C ₁ -C ₆ -alkylamines as defined above.

The term base, as defined herein, also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.

- 29 044989

Bases are usually used in excess, but they can also be used in equimolar amounts or, if appropriate, can be used as a solvent.

Preferably, 1 to 5 eq. is used. base, especially preferably 3 eq. bases relative to the guanidine salts of formula (V).

Completion of the reaction can be easily determined by one skilled in the art using conventional methods.

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.

Carbonyl compounds of formula (VI) necessary for the preparation of azines of formula (I) are known from the literature. They can be prepared according to known methods and/or are commercially available.

The guanidine salt of formula (V), where L ² represents iodine, necessary for the preparation of thiotriazines of formula (IV), is known from the literature (for example, M. Freund et al., Chem. Ber. 1901, 34, 3110 3122; H. Eilingsfeld et al., Chem. Ber. 1967, 100, 1874 - 1891).

Method B).

Azines of formula (I) can be prepared by reacting halotriazines of formula (II) with amines of formula (III) in the presence of a base and/or catalyst or in the presence of an acid as shown in the following Scheme 2:

(VH) (vi) (|)

The variables Q, Ra, R ^b , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and R ⁷ have meanings, in particular preferred values, as in formula (I) mentioned above, and L ¹ is an interchangeable a leaving group such as halogen, CN, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -alkoxycarbonyl, C ₁ -C ₆ -alkylcarbonyloxy or C1-C6 -alkoxycarbonyloxy;

preferably halogen or C ₁ -C ₆ -alkoxy;

particularly preferably Cl or C ₁ -C ₆ -alkoxy, also particularly preferably halogen;

particularly preferably Cl;

R ¹ represents H, C ₁ -C ₆ -alkyl;

particularly preferably R ¹ represents H; and R ⁵ represents H, C ₁ -C ₆ -alkyl;

preferably R ⁵ is H.

The reaction of biguanidines of formula (VII) with carbonyl compounds of formula (VI) is usually carried out at temperatures from 50°C to the boiling point of the reaction mixture, preferably from 50 to 200°C (for example, R. Sathunuru et al., J. Heterocycl. Chem. 2008, 45, 1673-1678).

The reaction can be carried out at atmospheric pressure or hanging pressure, if appropriate, under an inert gas atmosphere, continuously or in batches.

In one embodiment of the method according to the invention, biguanidines of formula (VII) and carbonyl compounds of formula (VI) are used in equimolar amounts.

In another embodiment of the method according to the invention, the carbonyl compounds of formula (VI) are used in excess relative to the biguanidines of formula (VII).

Preferably, the molar ratio of carbonyl compounds of formula (VIII) to biguanidines of formula (VII) is in the range from 1.5:1 to 1:1, preferably 1.2:1 to 1:1, especially preferably 1.2:1, also especially preferably 1:1.

The reaction of biguanidines of formula (VII) with carbonyl compounds of formula (VI) is carried out in an organic solvent.

Suitable solvents in principle are all which are capable of dissolving biguanidines of formula (VII) and carbonyl compounds of formula (VI) 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 methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), nitriles such such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, N,Ndimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N'dimethylpropylene urea ( DMPM), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP).

- 30 044989

Preferred solvents are ethers and dipolar aprotic solvents as defined above. More preferably, the solvents are ethers as defined above.

The term solvent, as used herein, also includes mixtures of two or more of the above compounds.

The reaction of guanidine salts of formula (VII) with a carbonyl compound of formula (VIII) is carried out in the presence of a base.

Examples of suitable bases include metal-containing bases and nitrogen-containing bases.

Examples of suitable metal-containing bases are inorganic compounds such as alkali metal oxide 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 and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate and calcium carbonate, as well as alkali metal bicarbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali and alkaline earth metal phosphates such as sodium phosphate, potassium phosphate and calcium phosphate; and, in addition, organic bases such as tertiary amines, such as tri-Cr C ₆ -alkylamines, for example triethylamine, trimethylamine, N-ethyl-diisopropylamine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine , N-methylmorpholine, as well as 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 tri-C ₁ -C ₆ -alkylamines as defined above.

The term base, as defined herein, also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.

Bases are usually used in excess, but they can also be used in equimolar amounts or, if appropriate, can be used as a solvent.

Preferably, 1 to 5 eq. is used. base, especially preferably 3 eq. bases relative to the biguanidines of formula (VII).

Completion of the reaction can be easily determined by one skilled in the art using conventional methods.

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.

Some intermediates and final products are obtained as viscous oils that can be purified or devolatilized under reduced pressure and moderately elevated temperature.

If the intermediates and final products are obtained in solid form, purification can also be carried out by recrystallization or hydrolytic resolution.

The carbonyl compounds of formula (VI) necessary for the preparation of azines of formula (I) are known in the art and/or are commercially available.

Biguanidines of formula (VII) necessary for the preparation of azines of formula (I) can be prepared by reacting cyanoguanidines of formula (IX) with amines of formula (II) in the presence of an acid

where A represents a substituent

The variables Q, R ^a , R ^b , R ² , R ³ , R ⁴ , R ⁶ , R ⁷ and R ⁷ have meanings, particularly preferred values, as in formula (I) mentioned above, and R ¹ is H, Cl-C ₆ -alkyl;

- 31 044989 particularly preferably R ¹ represents H; and R ⁵ represents H, C ₁ -C ₆ -alkyl;

also particularly preferably R ⁵ is H.

The reaction of guanidines of formula (IX) with amines of formula (II) is usually carried out at a temperature of from to 150°C, preferably from 80 to 130°C.

Microwaves have been used when appropriate (e.g. C.O. Kappe, A. Stadler, Microwaves in Organic and Medicinal Chemistry, Weinheim 2012).

The reaction can be carried out at atmospheric pressure or hanging pressure, if appropriate, under an inert gas atmosphere, continuously or in batches.

In one embodiment of the method according to the invention, guanidines of formula (IX) and amines of formula (II) are used in equimolar quantities.

In another embodiment of the method according to the invention, the amines of formula (II) are used in excess relative to the guanidines of formula (IX).

Preferably, the molar ratio of amines of formula (II) to guanidines of formula (IX) is in the range from 2:1 to 1:1, preferably from 1.5:1 to 1:1, particularly preferably 1:1.

The reaction of guanidines of formula (IX) with amines of formula (II) is carried out in an organic solvent.

Suitable solvents in principle are all which are capable of dissolving guanidines of formula (IX) and amines of formula (II) 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 methyl ether (TBME), dioxane, anisole and tetrahydrofuran (THF), nitriles such such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylαcetαmide (DMAC), 1,3-dimethyl-2imidazolidinone (DMI), K,K'-dimethylpropylene urea (DMPM), dimethyl sulfoxide (DMSO) and 1methyl-2 pyrrolidinone (NMP).

Preferred solvents are ethers, nitriles and dipolar aprotic solvents as defined above.

More preferably, the solvents are nitriles as defined above.

The term solvent, as used herein, also includes mixtures of two or more of the above solvents.

The reaction of guanidines of formula (IX) with amines of formula (II) is carried out in the presence of an acid.

Examples of suitable acids are inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, sulfuric acid, p-toluenesulfonic acid; Lewis acids such as boron trifluoride, aluminum chloride, ferric chloride III, tin chloride IV, titanium chloride IV and zinc II chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid can also be used acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid.

Acids are usually used in excess or, if appropriate, can be used as a solvent.

The treatment is carried out in a known manner.

The guanidines of formula (IX) needed to prepare the biguanides of formula (VII) are commercially available or can be prepared according to methods described in the literature (eg, J.L. LaMattina et al., J. Med. Chem. 1990, 33, 543-552 ; A. Perez-Medrano et al., J. Med. Chem. 2009, 52, 3366 - 3376).

The amines of formula (II) needed to prepare the biguanidines of formula (VII) are commercially available or can be prepared according to methods described in the literature (eg, Barnes et al., WO/2007/067612).

The compounds of formula (I) have herbicidal activity. Therefore, they can be used to control unwanted or unwanted plants or vegetation. They can also be used in a method for controlling unwanted or undesirable plants or vegetation, which includes causing the action of at least one compound (I) or a salt thereof on the plants, their environment or seeds. In order for a compound of formula (I) or a salt thereof to act on plants, their environment or seeds, the compounds of the present invention are applied to the plants, their environment or seeds of said plants.

To broaden the spectrum of action and achieve synergistic effects, the diaminotriazine compounds of formula (I) can be mixed with a large number of members of other herbicidal or growth-regulating groups of active ingredients and then used together.

Suitable components for mixtures are, for example, herbicides from the classes of acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofuran, benzoic acid, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenols, diphenyl ethers ov, glycines , imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoroamidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triketones, yay cils, ureas.

The invention also relates to combinations of diaminotriazine compounds of formula (I) with at least one additional herbicide B and/or at least one safener C).

The additional herbicidal compound B (component B) is in particular selected from the herbicide classes b1) to b15):

b1) lipid biosynthesis inhibitors;

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);

b9) mitosis inhibitors;

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

b11) cellulose biosynthesis inhibitors;

b12) dissociating herbicides;

b13) auxin herbicides;

b14) auxin transport inhibitors and b15) other herbicides selected from the group consisting of bromobutide, chloroflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapone, dazomet, difenzoquat, difenzoquat methyl sulfate, dimetipine, DSMA, dimron, endothal and its salts, etobenzanide, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamin-ammonium, indanofan, indaziflam, maleic acid hydrazide, mefluidide, metam, methiozolin ( CAS 403640-27-7), methyl azide, methyl bromide, methyl dimrone, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflame, tridifane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)- 4pyridazinol (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 that contain at least one herbicide B selected from herbicide classes b1, b6, b9, b10 and b11.

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

b1) from the group of lipid biosynthesis inhibitors:

ACC herbicides, such as aloxydim, aloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-R, fenoxaprop-R- ethyl, fluazifop, fluazifop-butyl, fluazifop-R, fluazifop-R-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-R, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop- tefuryl, quizalofop-R, quizalofop-R-ethyl, quizalofop-R-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4(4'-chloro-4-cyclopropyl-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-tetramethyl2H-pyran-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) -on (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- 2Hpyran-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-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-oxo-2H -pyran-3-ylcarboxylic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6tetramethyl-5-oxo-2H-pyran -3-ylcarboxylic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'- 33 044989 biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5- oxo-2H-pyran-3-ylcarboxylic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5oxo-2H-pyran- 3-ylcarboxylic acid methyl ester (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, thiocarbazyl, triallate and vernolate;

b2) from the group of ALS inhibitors:

sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, etamethsulfuron, etamethsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium , foramsulfuron, halosulfuron, halosulfuron- methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, p imsulfuron, sulfometuron, sulfometuron- methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron, imidazolinones such as imazamethabenz, imazamethabenzmethyl, imazamox, imazapic, imazapyr, imazaquin and imazet apir, triazolopyrimidine herbicides and sulfonanilides , such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, methosulam, penoxulam, pyrimisulfan and piroxulam, pyrimidinyl benzoates such as bispiribac, bispiribac-sodium, piribenzoxime, pyriftalide, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium th, difficult 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid 1-methylethyl ester (CAS 420138-41-6), 4-[[[ 2-[(4,6dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoic acid (CAS 420138-40-5), N-(4bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl )oxy]benzenemethanamine (CAS 420138-01-8), sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triathamon;

Among them, a preferred embodiment of the invention concerns those compositions that contain at least one imidazolinone herbicide;

b3) from the group of photosynthesis inhibitors:

amicarbazone, photosystem II inhibitors, for example, triazine herbicides, including chlorotriazine, triazinones, triazinediones, methylthiothriazines and pyridazinones, such as ametrine, atrazine, chloridazone, cyanazine, desmethrin, dimethamethrin, hexazinone, metribuzin, promethone, prometrin, propazine, simazine, symethrine, terbumetone, terbutylazine, terbutryn and trietazine, arylureas such as chlorbromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, metabenzthiazuron, metobenzuron, methoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenylcarbamates, such as desmedipham, carbutylate, phenmedipham, phenmediphamethyl, nitrile herbicides such as bromophenoxime, bromoxynil and its salts and esters, ioxynil and its salts and esters, uracils such as bromacil, lenacyl and terbacil, and bentazone and bentazone sodium, pyridate, pyridafol, pentanochlor and propanil and photosystem I inhibitors such as diquat, diquat dibromide, paraquat, paraquat dichloride and paraquat dimethyl sulfate. Among them, a preferred embodiment of the invention concerns those compositions that contain at least one aryl urea herbicide. Among them, a preferred embodiment of the invention concerns those compositions that contain at least one triazine herbicide. Among them, a preferred embodiment of the invention concerns those compositions that contain at least one nitrile herbicide;

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

acifluorfen, acifluorfen sodium, azaphenidine, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxifene, cynidon-ethyl, fluazolate, flufenpyr, flufenpyrethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycophene, f toroglycophen-ethyl, flutiacet, flutiacet-methyl, fomesafen, halosaphen, lactofen, oxadiargyl, oxadiazone, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimine, thiaphenacyl, 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]oxazin-6-yl]-1,5-dimethyl-6- thioxo-[1,3,5]triazinan-2,4-dione, 1,5-dimethyl-6-thioxo-3-(2,2,7trifluoro-3-oxo-4-(prop-2-ynyl)- 3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinan-2,4-dione (CAS 1258836-72-4), 2-(2 ,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)4,5,6,7-tetrahydroisoindole-1 ,3-dione, 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-inyl- 34 044989

3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidin-2,4-dione, methyl-(E)-4-[2-chloro-5-[4-chloro -5(difluoromethoxy)-1H-methylpyrazol-3-yl]-4-fluorophenoxy]-3-methoxy-but-2-enoate [CAS 948893-00-3] and 3[7-chloro-5-fluoro-2- (trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4dione (CAS 212754-02-4);

b5) from the group of whitening herbicides:

PDS inhibitors: beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-337), HPPD inhibitors: benzobicyclone, benzophenap, clomazone, phenquintrione , isoxaflutole, mesotrione, pyrasulfotole, pyrazolinate, pyrazoxifene, sulcotrione, tefuryltrione, tembotrione, topramesone and bicyclopyrone, bleaching agents of unknown purpose: aclonifen, amitrol and flumeturon;

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 (bialafos), bilanaphos sodium, glufosinate, glufosinate-P and glufosinate ammonium;

b8) from the group of DHP synthase inhibitors: asulam;

b9) from the group of mitosis inhibitors:

compounds from group K1: dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramids such as amiprofos, amiprofos-methyl and butamiphos, benzoin herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr; benzamides such as propyzamide and tebutam; compounds from group K2: chlorpropham, profame and carbetamide, among which compounds from group K1, in particular dinitroanilines, are preferred; b10) from the group of VLCFA inhibitors:

chloroacetamides such as acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, petoxamide, pretilachlor, propachlor, propisochlor and tenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as difen amide, naproanilide, napropamide and napropamide-M, tetrazolinones such as fentrazamide and other herbicides such as anilophos, cafenstrol, phenoxasulfone, 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

isoxazoline compounds of formula (II) are known from the literature, 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 oxyacetamides;

b11) from the group of cellulose biosynthesis inhibitors:

- 35 044989 chlorothiamide, diclobenil, flupoxam, isoxaben and 1-cyclohexyl-5-pentafluorophenyloxy-1 ⁴ [1,2,4,6]thiatriazin-3-ylamine;

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, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyraliddimethylammonium, aminopyralid-tris-( 2-hydroxypropyl)ammonium and its esters, benazoline, benazoline-ethyl, chloramben and its salts and esters, clomeprop, clopyralide and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichloroprop-P and its salts and esters, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-meptyl, halauxifene and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB 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;

b14) from the group of auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-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, fosamin, fosamin-ammonium, indanofan, indaziflam, maleic hydrazide acids, mefluidide, metham, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl dimron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam and tridifane.

Preferred B herbicides that can be used in combination with the compounds of formula (I) according to the present invention are:

b1) from the group of lipid biosynthesis inhibitors:

clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxapropR-ethyl, fluazifop-R-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-R-ethyl, quizalofop-R- tefuryl, sethoxydim, 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) -on (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- 2Hpyran-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-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-oxo-2H -pyran-3-ylcarboxylic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6tetramethyl-5-oxo-2H-pyran -3-ylcarboxylic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H -pyran-3-ylcarboxylic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5oxo-2H-pyran- 3-ylcarboxylic acid methyl ester (CAS 1033760-58-5); benfuresate, dimepiperate, EPTS, esprocarb, etofumesate, molinate, orbencarb, prosulfocarb, thiobencarb and triallate;

b2) from the group of ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron-methyl, bispiribac-sodium, chlorimuron-ethyl, chlorsulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, etamethsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupirsulfuron- methyl sodium foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metosulam, metsulfuron- methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxime, pyrimisulfan, pyrifthalide, pyriminobac-methyl, pyrithiobac-sodium, piroxsulam, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbozone-methyl, thifensulfuron -methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron and triafamone;

b3) from the group of photosynthesis inhibitors:

ametrine, amicarbazone, atrazine, bentazone, bentazone sodium, bromoxynil and its salts and complex

- 36 044989 esters, chloridazone, chlorotoluron, cyanazine, desmedipham, diquat dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, lenacyl, linuron, metamitron, metabenzthiazuron, metribuzin, paraquat, paraquat dichloride, phenmedipham , propanil, pyridate, simazine, terbutryn, terbutylazine and thidiazuron;

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

acifluorfen sodium, bencarbazone, benzphendizone, butafenacil, carfentrazone-ethyl, cynidone-ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycophen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazone, oxyfluorfen, pentoxazone, pyraflufen, pyraf lufen-ethyl, saflufenacil, sulfentrazone, thiaphenacyl, 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), Ntetrahydrofurfuryl-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-N-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]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione, 1,5-dimethyl-6-thioxo-3-(2, 2,7trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinan- 2,4-dione (CaS 1258836-72-4), 2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4 ]oxazin-6-yl)4,5,6,7-tetrahydro-isoindole-1,3-dione, 1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4- prop-2-ynyl3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidin-2,4-dione 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 whitening herbicides:

aclonifen, amitrol, beflubutamide, benzobicyclone, bicyclopyrone, clomazone, diflufenican, fenquintrione, flumeturon, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazone, picolinafen, pyrasulfotol, pyrazolinate, sulcotrione, tefuryltrione, tembotrione, topramesone and 4-(3trifluoromethylphenoxy)-2- (4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7);

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 and glufosinate-ammonium;

b8) from the group of DHP synthase inhibitors: asulam;

b9) from the group of mitosis inhibitors: benfluralin, dithiopyr, ethalfluralin, oryzalin, pendimethalin, thiazopyr and trifluralin;

b10) from the group of VLCFA inhibitors:

acetochlor, alachlor, anilofos, butachlor, cafenstrol, dimethenamid, dimethenamid-R, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamideM, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone, tenil chlorine and isoxazoline compounds of formulas II .1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as mentioned above;

b11) from the group of cellulose biosynthesis inhibitors: diclobenil, flupoxam, isoxaben and 1cyclohexyl-5-pentafluorophenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine;

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 esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr-meptyl, halauxifene and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-R and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac and triclopyr and its salts and esters;

b14) from the group of auxin transport inhibitors: diflufenzopyr and diflufenzopyr sodium;

b15) from the group of other herbicides: bromobutide, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, difenzoquat, difenzoquat-methyl sulfate, DSMA, dimron (= daimuron), flamprop, flamprop-isopropyl , flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, indanofan, indaziflam, metam, MSMA, oxaziclomefone, pyributicarb, triaziflam and tridifan.

Particularly preferred herbicides B which can be used in combination with the compounds A of formula (I) according to the present invention are:

b1) from the group of lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyhalofopbutyl, fenoxaprop-R-ethyl, pinoxaden, profoxydim, 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-2H-pyran-3(6H) -on (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) -on (CAS 1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6

- 37 044989 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-2,2,6,6-tetramethyl- 2Hpyran-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-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-oxo-2H -pyran-3-ylcarboxylic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6tetramethyl-5-oxo-2H-pyran -3-ylcarboxylic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H -pyran-3-ylcarboxylic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5oxo-2H-pyran- 3-ylcarboxylic acid methyl ester (CAS 1033760-58-5); esprocarb, prosulfocarb, thiobencarb and triallate;

b2) from the group of ALS inhibitors: bensulfuron-methyl, bispiribac-sodium, cyclosulfamuron, diclosulam, flumetsulam, flupirsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron , iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsulam, propoxycarbazone-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbozone-methyl, tritosulfuron and triafamone;

b3) from the group of photosynthesis inhibitors: ametrine, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat dichloride, propanil, terbutryn and terbutylazine;

b4) from the group of protoporphyrinogen-HC oxidase inhibitors: flumioxazin, oxyfluorfen, saflufenacil, sulfentrazone, 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), 3-[7-fluoro-3-oxo-4(prop-2-ynyl)-3, 4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione, 1,5-dimethyl- 6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6yl) -1,3,5-triazinan-2,4-dione (CAS 1258836-72-4), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4- dihydro2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione and 1-methyl-6-trifluoromethyl-3-(2,2,7trifluoro- 3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidin-2,4-dione;

b5) from the group of bleaching herbicides: amitrol, bicyclopyrone, clomazone, diflufenican, fenquintrione, flumeturon, flurochloridone, isoxaflutole, mesotrione, picolinafen, sulcotrione, tefuryltrione, tembotrione and topramesone;

b6) from the group of EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium and glyphosate trimesium (sulfosate);

b7) from the group of glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;

b9) from the group of mitosis inhibitors: pendimethalin and trifluralin;

b10) from the group of VLCFA inhibitors: acetochlor, cafenstrol, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone; preference is also given to the isoxazoline compounds of formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as mentioned above;

b11) from the group of cellulose biosynthesis inhibitors: isoxaben;

b13) from the group of auxin herbicides: 2,4-D and its salts and esters, such as claciphos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and esters, clopyralid and its salts and esters, dicamba and its salts and esters, fluroxypyr-meptyl, quinclorac and quinmerac;

b14) from the group of auxin transport inhibitors: diflufenzopyr and diflufenzopyr sodium;

b15) from the group of other herbicides: dimron (= daimuron), indanofan, indaziflam, oxaziclomefone and triaziflam.

The active compounds B and C having a carboxyl group can be used in the form of an acid, in the form of an agriculturally acceptable salt as mentioned above, as well as in the form of an agriculturally acceptable derivative in the compositions of the invention.

In the case of dicamba, suitable salts are those in which the counterion is an agriculturally acceptable cation. For example, suitable dicamba salts include dicamba sodium, dicamba potassium, dicamba methyl ammonium, dicamba dimethyl ammonium, dicamba isopropylammonium, dicamba diglycolamine, dicamba olamine, dicamba diolamine, dicamba trolamine, dicamba-K,K-bis- (3aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of suitable esters are dicamba-methyl and dicamba-butotyl.

Suitable 2,4-D salts are 2,4-O-ammonium, 2,4-O-dimethylammonium, 2,4-D-diethylammonium, 2,4-O-diethanolammonium (2,4-O-diolamine), 2 ,4-D-triethanolammonium, 2,4-O-isopropylammonium, 2,4-Dtriisopropanolammonium, 2,4-O-heptylammonium, 2,4-O-dodecylammonium, 2,4-O-tetradecylammonium, 2,4D-triethylammonium , 2,4-D-tris-(2-hydroxypropyl)ammonium, 2,4-D-tris-(isopropyl)ammonium, 2,4-Dtrolamine, 2,4-D-lithium, 2,4-D-sodium . Examples of suitable 2,4-D esters are 2,4-D-38 044989 butothyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-O-butyl, 2, 4-O-ethyl, 2,4-O-ethylhexyl, 2,4D-isobutyl, 2,4-O-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D- methyl, 2,4-O-octyl, 2,4-O-pentyl,

2,4-O-propyl, 2,4-O-tefuryl and clacifos.

Suitable 2,4-DB salts are, for example, 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DBdimethylammonium. Suitable 2,4-DB esters are, for example, 2,4-OB-6util and 2,4-DBisoctyl.

Suitable dichlorprop salts are, for example, sodium dichlorprop, potassium dichlorprop and dichlorprop-dimethylammonium. Examples of suitable dichlorprop esters are dichlorprop-butotyl and dichlorprop-isoctyl.

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

A suitable MSRP salt is sodium MSRP. A suitable MSRP ester is MSRB-ethyl.

Suitable clopyralid salts are clopyralid potassium, clopyralid olamine and clopyralid tris(2-hydroxypropyl)ammonium. An example of a suitable clopyralid ester 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-isoctyl.

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

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

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

Suitable glyphosate salts are, for example, glyphosate ammonium, glyphosate diammonium, glyphosate dimethyl ammonium, glyphosate isopropylammonium, glyphosate potassium, glyphosate sodium, glyphosate trimesium, also ethanolamine and diethanolamine salts, preferably glyphosate diammonium, glyphosate isopropylammonium and glyphosate osat- trimesium (sulfosate).

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

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

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

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

Suitable salts and esters of mecoprop are mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.

Suitable salts of mecoprop-R are, for example, mecoprop-R-butotyl, mecoprop-Rdimethylammonium, mecoprop-R-2-ethylhexyl, mecoprop-R-isobutyl, mecoprop-R-potassium and mecoprop-R sodium.

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

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

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

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

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

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

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

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

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

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

- 39 044989

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

Particularly preferred herbicidal compounds B are herbicides B as defined above; in particular, herbicides B.1 - B.203, listed below in table. IN.

Herbicide B IN 1 clethodim AT 2 clodinofop-propargyl V.Z cycloxydim AT 4 cyhalofop-butyl AT 5 fenoxaprop-ethyl AT 6 fenoxaprop-R-ethyl AT 7 metamifop AT 8 pinoxaden AT 9 profoxydim AT 10 methoxydim AT 11 tepraloxydim AT 12 tralkoxydim B.13 esprocarb B.14 this is a fumesate B.15 molinate V.16 prosulfocarb B.17 thiobencarb V.18 triallate V.19 bensulfuron-methyl IN 20 bispiribac sodium AT 21 cloransulam-methyl V.22 chlorsulfuron V.23 clorimuron V.24 cyclosulfamuron V.25 diclosulam V.26 florasulam V.27 flumetsulam V.28 flupirsulfuron-methylsodium V.29 foramsulfuron V.ZO imazamox B.31 imazamox-ammonium V. 32 imazapic V.ZZ imazapic-ammonium V. 34 imazapic-isopropylammonium V.35 imazapyr V. 36 imazapyr-ammonium

Table B

Herbicide B V.37 imazapyr-isopropylammonium V.38 imazaquin V.39 imasaquin ammonium B.40 imazethapyr V.41 imazethapyr ammonium V.42 imazethapyrisopropylammonium V.43 imazosulfuron V.44 Iodosulfuron-methyl-sodium V.45 iofensulfuron V.46 iofensulfuron sodium V.47 mesosulfuron-methyl V.48 metazosulfuron V.49 metsulfuron-methyl V.50 methosulam V.51 nicosulfuron V.52 penoxulam V.53 propoxycarbazone sodium V.54 pyrazosulfuron-ethyl V.55 pyribenzoxime V.56 pyrifthalide V.57 pyroxulam V.58 propyrisulfuron V.59 rimsulfuron B.60 sulfosulfuron V.61 thiencarbazone-methyl V.62 thifensulfuron-methyl V.63 tribenuron-methyl V.64 tritosulfuron V.65 triathamon V.66 ametrine V.67 atrazine V.68 bentazone V.69 bromoxynil V.70 bromoxynyl octanoate V.71 bromoxynyl heptanoate V.72 bromoxynyl potassium

- 40 044989

V.73 diuron V. 74 fluometuron V.75 hexase inone V.76 isoproturon V.77 linuron V.78 metamitron V.79 metribuzin V.80 propanil V.81 simazine V. 82 terbutylazine V.83 terbutryn V. 84 paraquat dichloride V.85 acifluorfen V. 86 butafenacil V.87 carfentrazone-ethyl V.88 flumioxazin V.89 fomesafen V.90 oxadiargyl V.91 oxyfluorfen V. 92 pyraflufen V.93 pyraflufen-ethyl V. 94 saflufenacil V.95 sulfentrazone V. 96 trifludimooxazine V.97 ethyl [3-[2-chloro-4-fluoro-5-(1methyl-6-trifluoromethyl-2,4dioxo-1,2,3,4- tetrahydropyrimidin-3 yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-3Ιό) V.98 benzobicyclone V.99 bicyclopyrone V. 100 clomazone V.101 diflufenican V. 102 flurochloridone V. 103 isoxaflutole V. 104 mesotrione V.105 norflurazon V. 106 picolinafen V. 107 sulcotrione V. 108 tefuryltrione V. 109 tembotrione V.110 tolpyralate V.111 topramesone V.112 topramesone sodium V.113 amitrol V.114 fluometuron V.115 phenquintrione V.116 glyphosate V.117 glyphosate ammonium

B.118 glyph osat-dimethyl ammonium B.119 glyphosate isopropylammonium V. 120 glyphosate trimesium (sulfosate) V.121 glyphosate-potassium V. 122 glufosinate V. 123 glufosinate ammonium V. 124 glufosinate-R V. 125 glufosinate-P-ammonium V. 126 pendimethalin V. 127 trifluralin V. 128 acetochlor V. 129 butachlor V. 130 cafenstrol V.131 dimethenamid-R V. 132 fentr azamide V. 133 flufenacet V. 134 mefenacet V. 135 metazachlor V. 136 metolachlor V. 137 S-metolachlor V. 138 pretilachlor V. 139 phenoxasulfone V. 140 indaziflam V.141 isoxaben V. 142 triaziflam V. 143 ipfencarbazone V. 144 pyroxasulfone V. 145 2,4-D V. 146 2,4-O-isobutyl V. 147 2,4-O-dimethylammonium V. 148 2,4-D-N,N,N- trimethylethanolammonium V. 149 aminopyralide V. 150 aminopyralid-methyl V.151 aminopyralide-dimethylammonium V. 152 aminopyralide-tris(2hydroxypropyl)ammonium V. 153 clopyralid V. 154 clopyralid-methyl V. 155 clopyralide-olamine V. 156 dicamba V. 157 dicamba-butothyl V. 158 dicamba-diglycolamine V. 159 dicamba-dimethylammonium V. 160 dicamba diolamine V.161 dicamba isopropylammonium V. 162 dicamba potassium V. 163 dicamba sodium

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V. 164 dicamba-trolamine V.165 dicamba-M,M-bis-(3- aminopropyl)methylamine V. 166 dicamba-diethylenetriamine V.167 fluroxypyr V.168 fluroxypyr-meptyl V.169 halauxifene V. 170 halauxifene-methyl V.171 MSRA V. 172 MCPA-2-ethylhexyl V. 173 MCPA-dimethylammonium V. 174 quinclorac V. 175 quinclorac-dimethylammonium V. 176 queenmerac V. 177 quinmerac-dimethylammonium V. 178 florpirauxifene V. 179 florpyrauxifene benzyl (CAS 1390661-72-9) V. 180 aminocyclopyrachlor V.181 aminocyclopyrachlor-potassium V. 182 aminocyclopyrachlor-methyl V. 183 diflufenzopyr V. 184 diflufenzopyr sodium V. 185 dimron V. 186 indanofan

V. 187 oxaziclomefone V. 188 II. 1 V. 189 II.2 V. 190 II. 3 V.191 II.4 V. 192 II. 5 V. 193 II. 6 V. 194 II. 7 V. 195 II. 8 V. 196 II. 9 V. 197 4-amino-3-chloro-5-fluoro-6-(7fluoro-1 H-ind ol-6- yl)picolinic acid (CAS 1629965-65-6) V. 198 flopyrauxifene V. 199 oxotrione (CAS 1486617-213) V.200 cinmethylin V.201 2-chloro-3-methylsulfanyl-N(1-methyltetrazol-5-yl)-4(trifluoromethyl)benzamide (CAS 1361139-71-0) V.202 2-(2,4-dichlorophenyl)methyl- 4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9) V.203 cyclopyranyl

However, 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 that prevent or reduce damage to beneficial plants without significantly affecting the herbicidal action of the compounds of formula (I) on undesirable plants. They can be used either before sowing (for example, treating seeds, shoots or seedlings), or as a pre-emergence or post-emergence treatment of useful plants. 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 acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl -1 H-pyrazole-3,5 dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-hydroxyiminophenylacetonitriles, acetophenonoxyimines, 4,6-dihalo-2-phenylpyrimidines, N-[ [4(aminocarbonyl)phenyl]sulfonyl]-2-benzoylamides, 1,8-naphthalene anhydride, 2-halo-4-(haloalkyl)5-thiazolecarboxylic acids, phosphorothiolates and N-alkyl-O-phenyl-carbamates, as well as their agriculturally acceptable salts and their agriculturally acceptable derivatives, such as amides, esters and thioesters, provided they have an acid group.

Examples of preferred safeners C are benoxacor, cloquintocet, ciometrinil, cyprosulfamide, dichloromide, dicyclonone, dietolate, fenclorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalene anhydride, oxabetrinil, 4-(dichloroacetyl)1-ox a-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 N.W cloquintocet-mexyl C.5 dichlormide P.7 fenkl or az o l-these l P.9 furyl azole P.11 isoxadifen-ethyl P.13 mefenpyr-diethyl P.15 4-(dichloroacetyl)-1-oxa-4azaspiro[4.51decane P.17 K-(2-methoxybenzoyl)-4[(methylaminocarbonyl)amino]benzenesulfonamide

Table C

C.2 cloquintocet C.4 cyprosulfamide C.6 fenclorazole P.8 fenklorim P.10 isoxadifene P.12 mefenpir P.14 naphthalic anhydride P.16 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolid in P.17 metcamifene

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Active compounds B of groups b1) - b15) and safeners 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, Supplement for the 7th edition, 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 assignment of corresponding mechanisms of action to active compounds is based on current knowledge. If one active compound has multiple mechanisms of action, only one mechanism of action has been assigned to that substance.

The following combinations, designated by the code A-X.Y.Z, represent individual options for real-

tions of the invention. A-1.1.1 - A-1.727.3671, A-19.1.1 - A-19.727.3671, 5 A-2.1.1 - A-2.727.3671, A-20.1.1 - A-20.727.3671, A-3.1.1 - A-3.727.3671, 25 A-21.1.1 - A-21.727.3671, A-4.1.1 - A-4.727.3671, A-22.1.1 - A-22.727.3671, A-5.1.1 - A-5.727.3671, A-23.1.1 - A-23.727.3671, A-6.1.1 - A-6.727.3671, A-24.1.1 - A-24.727.3671, 10 A-7.1.1 - A-7.727.3671, A-25.1.1 - A-25.727.3671, A-8.1.1 - A-8.727.3671, thirty A-26.1.1 - A-26.727.3671, A-9.1.1 - A-9.727.3671, A-27.1.1 - A-27.727.3671, A-10.1.1 - A-10.727.3671, A-28.1.1 - A-28.727.3671, A-11.1.1 - A-11.727.3671, A-29.1.1 - A-29.727.3671, 15 A-12.1.1 - A-12.727.3671, A-30.1.1 - A-30.727.3671, A-13.1.1 - A-13.727.3671, 35 A-31.1.1 -A-31.727.3671, A-14.1.1 - A-14.727.3671, A-32.1.1 - A-32.727.3671, A-15.1.1 - A-15.727.3671, A-33.1.1 - A-33.727.3671, A-16.1.1 - A-16.727.3671, A-34.1.1 - A-34.727.3671, 20 A-17.1.1 - A-17.727.3671, A-35.1.1 - A-35.727.3671. A-18.1.1 - A-18.727.3671, 40

In the above codes, A-X refers to the numbers in the table. A-1-A.35. The integer Y refers to the row in the table. A, while the integer Z refers to the series of the table. 1 below.

However, code A-1.1.1 refers to the combination of a compound of formula Ia of table. A-1, where X and R ² are as defined in row 1 of the table. A, with a combination of herbicide B and safener C, defined in combination No. 1.1 of table. 1.

Code A-12.2.35 refers to the combination of a compound of formula Ia of table. A-12, where X and R ² are as defined in row 2 of the table. A, with a combination of herbicide B and safener C, defined in combination No. 1.35 of table. 1.

Code A-35.300. 3671 refers to a combination of a compound of formula Ia table. A-35, where X and R ² are as defined in row 300 of table. A, with a combination of herbicide B and safener C, defined in combination No. 1.3456 table. 1.

Conn. No. herbicide B safener S 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 —

Conn. No. herbicide B safener S 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 V.16 —

Table 1

Conn. No. herbicide B safener S 1.17 B.17 — 1.18 V.18 — 1.19 V.19 — 1.20 IN 20 — 1.21 AT 21 — 1.22 V.22 — 1.23 V.23 — 1.24 V.24 —

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1.25 B.25 — 1.78 V.78 — 1.131 V.131 — 1.26 B.26 — 1.79 V.79 — 1.132 V.132 — 1.27 B.27 — 1.80 V.80 — 1.133 V.133 — 1.28 B.28 — 1.81 V.81 — 1.134 V.134 — 1.29 B.29 — 1.82 V.82 — 1.135 V.135 — 1.30 V.ZO — 1.83 V.83 — 1.136 V.136 — 1.31 B.31 — 1.84 V.84 — 1.137 V.137 — 1.32 V.32 — 1.85 V.85 — 1.138 V.138 — 1.33 V.ZZ — 1.86 V.86 — 1.139 V.139 — 1.34 V.34 — 1.87 V.87 — 1.140 V.140 — 1.35 V.35 — 1.88 V.88 — 1.141 V.141 — 1.36 V.36 — 1.89 V.89 — 1.142 V.142 — 1.37 V.37 — 1.90 V.90 — 1.143 V.143 — 1.38 V.38 — 1.91 V.91 — 1.144 V.144 — 1.39 V.39 — 1.92 V.92 — 1.145 V.145 — 1.40 B.40 — 1.93 V.93 — 1.146 V.146 — 1.41 V.41 — 1.94 V.94 — 1.147 V.147 — 1.42 V.42 — 1.95 V.95 — 1.148 V.148 — 1.43 V.43 — 1.96 V.96 — 1.149 V.149 — 1.44 V.44 — 1.97 V.97 — 1.150 V.150 — 1.45 V.45 — 1.98 V.98 — 1.151 V.151 — 1.46 V.46 — 1.99 V.99 — 1.152 V.152 — 1.47 V.47 — 1.100 V.100 — 1.153 V.153 — 1.48 V.48 — 1.101 V.101 — 1.154 V.154 — 1.49 V.49 — 1.102 V.102 — 1.155 V.155 — 1.50 V.50 — 1.103 V.103 — 1.156 V.156 — 1.51 V.51 — 1.104 V.104 — 1.157 V.157 — 1.52 V.52 — 1.105 V.105 — 1.158 V.158 — 1.53 V.53 — 1.106 V.106 — 1.159 V.159 — 1.54 V.54 — 1.107 V.107 — 1.160 V.160 — 1.55 V.55 — 1.108 V.108 — 1.161 V.161 — 1.56 V.56 — 1.109 V.109 — 1.162 V.162 — 1.57 V.57 — 1.110 V.110 — 1.163 V.163 — 1.58 V.58. — 1.111 V.111 — 1.164 V.164 — 1.59 V.59 — 1.112 V.112 — 1.165 V.165 — 1.60 B.60 — 1.113 V.IZ — 1.166 V.166 — 1.61 V.61 — 1.114 V.114 — 1.167 V.167 — 1.62 V.62 — 1.115 V.115 — 1.168 V.168 — 1.63 V.63 — 1.116 V.116 — 1.169 V.169 — 1.64 V.64 — 1.117 V.117 — 1.170 V.170 — 1.65 V.65 — 1.118 V.118 — 1.171 V.171 — 1.66 V.66 — 1.119 V.119 — 1.172 V.172 — 1.67 V.67 — 1.120 V.120 — 1.173 V.173 — 1.68 V.68 — 1.121 V.121 — 1.174 V.174 — 1.69 V.69 — 1.122 V.122 — 1.175 V.175 — 1.70 V.70 — 1.123 V.123 — 1.176 V.176 — 1.71 V.71 — 1.124 V.124 — 1.177 V.177 — 1.72 V.72 — 1.125 V.125 — 1.178 V.178 — 1.73 V.73 — 1.126 V.126 — 1.179 V.179 — 1.74 V.74 — 1.127 V.127 — 1.180 V.180 — 1.75 V.75 — 1.128 V.128 — 1.181 V.181 — 1.76 V.76 — 1.129 V.129 — 1.182 V.182 — 1.77 V.77 — 1.130 V.130 — 1.183 V.183 —

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1.204 IN 1 C.1 1.205 AT 2 C.1 1.206 V.Z C.1 1.207 AT 4 C.1 1.208 AT 5 C.1 1.209 AT 6 C.1 1.210 AT 7 C.1 1.211 AT 8 C.1 1.212 AT 9 C.1 1.213 AT 10 C.1 1.214 IN AND C.1 1.215 AT 12 C.1 1.216 B.13 C.1 1.217 B.14 C.1 1.218 B.15 C.1 1.219 V.16 C.1 1.220 B.17 C.1 1.221 V.18 C.1 1.222 V.19 C.1 1.223 IN 20 C.1 1.224 AT 21 C.1 1.225 V.22 C.1 1.226 V.23 C.1 1.227 V.24 C.1 1.228 V.25 C.1 1.229 V.26 C.1 1.230 V.27 C.1 1.231 V.28 C.1 1.232 V.29 C.1 1.233 V.ZO C.1 1.234 B.31 C.1 1.235 V.32 C.1 1.236 V.ZZ C.1 1.237 V.34 C.1 1.238 V.35 C.1 1.239 V.36 C.1 1.240 V.37 C.1 1.241 V.38 C.1 1.242 V.39 C.1 1.243 B.40 C.1 1.244 V.41 C.1 1.245 V.42 C.1 1.246 V.43 C.1 1.247 V.44 C.1 1.248 V.45 C.1 1.249 V.46 C.1 1.250 V.47 C.1 1.251 V.48 C.1 1.252 V.49 C.1 1.253 V.50 C.1 1.254 V.51 C.1 1.255 V.52 C.1 1.256 V.53 C.1 1.257 V.54 C.1 1.258 V.55 C.1

1.259 V.56 C.1 1.260 V.57 C.1 1.261 V.58. C.1 1.262 V.59 C.1 1.263 B.60 C.1 1.264 V.61 C.1 1.265 V.62 C.1 1.266 V.63 C.1 1.267 V.64 C.1 1.268 V.65 C.1 1.269 V.66 C.1 1.270 V.67 C.1 1.271 V.68 C.1 1.272 V.69 C.1 1.273 V.70 C.1 1.274 V.71 C.1 1.275 V.72 C.1 1.276 V.73 C.1 1.277 V.74 C.1 1.278 V.75 C.1 1.279 V.76 C.1 1.280 V.77 C.1 1.281 V.78 C.1 1.282 V.79 C.1 1.283 V.80 C.1 1.284 V.81 C.1 1.285 V.82 C.1 1.286 V.83 C.1 1.287 V.84 C.1 1.288 V.85 C.1 1.289 V.86 C.1 1.290 V.87 C.1 1.291 V.88 C.1 1.292 V.89 C.1 1.293 V.90 C.1 1.294 V.91 C.1 1.295 V.92 C.1 1.296 V.93 C.1 1.297 V.94 C.1 1.298 V.95 C.1 1.299 V.96 C.1 1.300 V.97 C.1 1.301 V.98 C.1 1.302 V.99 C.1 1.303 V.100 C.1 1.304 V.101 C.1 1.305 V. 102 C.1 1.306 V.103 C.1 1.307 V. 104 C.1 1.308 V.105 C.1 1.309 V.106 C.1 1.310 V.107 C.1 1.311 V.108 C.1 1.312 V.109 C.1 1.313 V.110 C.1 1.314 V.111 C.1

1.315 V.112 C.1 1.316 V.IZ C.1 1.317 V.114 C.1 1.318 V.115 C.1 1.319 V.116 C.1 1.320 V.117 C.1 1.321 V.118 C.1 1.322 V.119 C.1 1.323 V.120 C.1 1.324 V.121 C.1 1.325 V.122 C.1 1.326 V.123 C.1 1.327 V.124 C.1 1.328 V.125 C.1 1.329 V.126 C.1 1.330 V.127 C.1 1.331 V.128 C.1 1.332 V.129 C.1 1.333 V.130 C.1 1.334 V.131 C.1 1.335 V.132 C.1 1.336 V.133 C.1 1.337 V.134 C.1 1.338 V.135 C.1 1.339 V.136 C.1 1.340 V.137 C.1 1.341 V.138 C.1 1.342 V.139 C.1 1.343 V.140 C.1 1.344 V.141 C.1 1.345 V.142 C.1 1.346 V.143 C.1 1.347 V.144 C.1 1.348 V.145 C.1 1.349 V.146 C.1 1.350 V.147 C.1 1.351 V.148 C.1 1.352 V.149 C.1 1.353 V.150 C.1 1.354 V.151 C.1 1.355 V.152 C.1 1.356 V.153 C.1 1.357 V.154 C.1 1.358 V.155 C.1 1.359 V.156 C.1 1.360 V.157 C.1 1.361 V.158 C.1 1.362 V.159 C.1 1.363 V.160 C.1 1.364 V.161 C.1 1.365 V.162 C.1 1.366 V.163 C.1 1.367 V.164 C.1 1.368 V.165 C.1 1.369 V.166 C.1 1.370 V.167 C.1

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1.371 V.168 C.1 1.372 V.169 C.1 1.373 V.170 C.1 1.374 V.171 C.1 1.375 V.172 C.1 1.376 V.173 C.1 1.377 V.174 C.1 1.378 V.175 C.1 1.379 V.176 C.1 1.380 V.177 C.1 1.381 V.178 C.1 1.382 V.179 C.1 1.383 V.180 C.1 1.384 V.181 C.1 1.385 V.182 C.1 1.386 V.183 C.1 1.387 V.184 C.1 1.388 V.185 C.1 1.389 V.186 C.1 1.390 V.187 C.1 1.391 V.188 C.1 1.392 V.189 C.1 1.393 V.190 C.1 1.394 V.191 C.1 1.395 V.192 C.1 1.396 V.193 C.1 1.397 V.194 C.1 1.398 V.195 C.1 1.399 V.196 C.1 1.400 V.197 C.1 1.401 V.198 C.1 1.402 V.199 C.1 1.403 V.200 C.1 1.404 V.201 C.1 1.405 V.202 C.1 1.406 V.203 C.1

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1.407 B.l C.2 1.408 B.2 C.2 1.409 V.Z C.2 1.410 B.4 C.2 1.411 AT 5 C.2 1.412 AT 6 C.2 1.413 AT 7 C.2 1.414 AT 8 C.2 1.415 AT 9 C.2 1.416 AT 10 C.2 1.417 IN AND C.2 1.418 AT 12 C.2 1.419 B.13 C.2 1.420 B.14 C.2 1.421 B.15 C.2 1.422 V.16 C.2 1.423 B.17 C.2 1.424 V.18 C.2 1.425 V.19 C.2 1.426 IN 20 C.2 1.427 AT 21 C.2 1.428 V.22 C.2 1.429 V.23 C.2 1.430 V.24 C.2 1.431 V.25 C.2 1.432 V.26 C.2 1.433 V.27 C.2 1.434 V.28 C.2 1.435 V.29 C.2 1.436 B.30 C.2 1.437 B.31 C.2 1.438 V.32 C.2 1.439 V.ZZ C.2 1.440 V.34 C.2 1.441 V.35 C.2 1.442 V.36 C.2 1.443 V.37 C.2 1.444 V.38 C.2 1.445 V.39 C.2 1.446 B.40 C.2 1.447 V.41 C.2 1.448 V.42 C.2 1.449 V.43 C.2 1.450 V.44 C.2 1.451 V.45 C.2 1.452 V.46 C.2 1.453 V.47 C.2 1.454 V.48 C.2 1.455 V.49 C.2 1.456 V.50 C.2 1.457 V.51 C.2 1.458 V.52 C.2 1.459 V.53 C.2 1.460 V.54 C.2 1.461 V.55 C.2

1.462 V.56 C.2 1.463 V.57 C.2 1.464 V.58. C.2 1.465 V.59 C.2 1.466 B.60 C.2 1.467 V.61 C.2 1.468 V.62 C.2 1.469 V.63 C.2 1.470 V.64 C.2 1.471 V.65 C.2 1.472 V.66 C.2 1.473 V.67 C.2 1.474 V.68 C.2 1.475 V.69 C.2 1.476 V.70 C.2 1.477 V.71 C.2 1.478 V.72 C.2 1.479 V.73 C.2 1.480 V.74 C.2 1.481 V.75 C.2 1.482 V.76 C.2 1.483 V.77 C.2 1.484 V.78 C.2 1.485 V.79 C.2 1.486 V.80 C.2 1.487 V.81 C.2 1.488 V.82 C.2 1.489 V.83 C.2 1.490 V.84 C.2 1.491 V.85 C.2 1.492 V.86 C.2 1.493 V.87 C.2 1.494 V.88 C.2 1.495 V.89 C.2 1.496 V.90 C.2 1.497 V.91 C.2 1.498 V.92 C.2 1.499 V.93 C.2 1.500 V.94 C.2 1.501 V.95 C.2 1.502 V.96 C.2 1.503 V.97 C.2 1.504 V.98 C.2 1.505 V.99 C.2 1.506 V.100 C.2 1.507 V.101 C.2 1.508 V. 102 C.2 1.509 V.103 C.2 1.510 V. 104 C.2 1.511 V.105 C.2 1.512 V.106 C.2 1.513 V.107 C.2 1.514 V.108 C.2 1.515 V.109 C.2 1.516 V.110 C.2 1.517 V.111 C.2

1.518 V.112 C.2 1.519 V.IZ C.2 1.520 V.114 C.2 1.521 V.115 C.2 1.522 V.116 C.2 1.523 V.117 C.2 1.524 V.118 C.2 1.525 V.119 C.2 1.526 V.120 C.2 1.527 V.121 C.2 1.528 V.122 C.2 1.529 V.123 C.2 1.530 V.124 C.2 1.531 V.125 C.2 1.532 V.126 C.2 1.533 V.127 C.2 1.534 V.128 C.2 1.535 V.129 C.2 1.536 V.130 C.2 1.537 V.131 C.2 1.538 V.132 C.2 1.539 V.133 C.2 1.540 V.134 C.2 1.541 V.135 C.2 1.542 V.136 C.2 1.543 V.137 C.2 1.544 V.138 C.2 1.545 V.139 C.2 1.546 V.140 C.2 1.547 V.141 C.2 1.548 V.142 C.2 1.549 V.143 C.2 1.550 V.144 C.2 1.551 V.145 C.2 1.552 V.146 C.2 1.553 V.147 C.2 1.554 V.148 C.2 1.555 V.149 C.2 1.556 V.150 C.2 1.557 V.151 C.2 1.558 V.152 C.2 1.559 V.153 C.2 1.560 V.154 C.2 1.561 V.155 C.2 1.562 V.156 C.2 1.563 V.157 C.2 1.564 V.158 C.2 1.565 V.159 C.2 1.566 V.160 C.2 1.567 V.161 C.2 1.568 V.162 C.2 1.569 V.163 C.2 1.570 V.164 C.2 1.571 V.165 C.2 1.572 V.166 C.2 1.573 V.167 C.2

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1.574 V.168 C.2 1.575 V.169 C.2 1.576 V.170 C.2 1.577 V.171 C.2 1.578 V.172 C.2 1.579 V.173 C.2 1.580 V.174 C.2 1.581 V.175 C.2 1.582 V.176 C.2 1.583 V.177 C.2 1.584 V.178 C.2 1.585 V.179 C.2 1.586 V.180 C.2 1.587 V.181 C.2 1.588 V.182 C.2 1.589 V.183 C.2 1.590 V.184 C.2 1.591 V.185 C.2 1.592 V.186 C.2 1.593 V.187 C.2 1.594 V.188 C.2 1.595 V.189 C.2 1.596 V.190 C.2 1.597 V.191 C.2 1.598 V.192 C.2 1.599 V.193 C.2 1.600 V.194 C.2 1.601 V.195 C.2 1.602 V.196 C.2 1.603 V.197 C.2 1.604 V.198 C.2 1.605 V.199 C.2 1.606 V.200 C.2 1.607 V.201 C.2 1.608 V.202 C.2 1.609 V.203 C.2

- 48 044989

1.610 B.l N.W 1.611 B.2 N.W 1.612 V.Z N.W 1.613 B.4 N.W 1.614 AT 5 N.W 1.615 AT 6 N.W 1.616 AT 7 N.W 1.617 AT 8 N.W 1.618 AT 9 N.W 1.619 AT 10 N.W 1.620 AT 11 N.W 1.621 AT 12 N.W 1.622 B.13 N.W 1.623 B.14 N.W 1.624 B.15 N.W 1.625 V.16 N.W 1.626 B.17 N.W 1.627 V.18 N.W 1.628 V.19 N.W 1.629 IN 20 N.W 1.630 AT 21 N.W 1.631 V.22 N.W 1.632 V.23 N.W 1.633 V.24 N.W 1.634 V.25 N.W 1.635 V.26 N.W 1.636 V.27 N.W 1.637 V.28 N.W 1.638 V.29 N.W 1.639 V.ZO N.W 1.640 B.31 N.W 1.641 V.32 N.W 1.642 V.ZZ N.W 1.643 V.34 N.W 1.644 V.35 N.W 1.645 V.36 N.W 1.646 V.37 N.W 1.647 V.38 N.W 1.648 V.39 N.W 1.649 B.40 N.W 1.650 V.41 N.W 1.651 V.42 N.W 1.652 VAZ N.W 1.653 V.44 N.W 1.654 V.45 N.W 1.655 V.46 nw 1.656 V.47 N.W 1.657 V.48 N.W 1.658 V.49 N.W 1.659 V.50 N.W 1.660 V.51 N.W 1.661 V.52 N.W 1.662 V.53 N.W 1.663 V.54 N.W 1.664 V.55 N.W

1.665 V.56 N.W 1.666 V.57 N.W 1.667 V.58. N.W 1.668 V.59 N.W 1.669 B.60 N.W 1.670 V.61 N.W 1.671 V.62 N.W 1.672 V.63 N.W 1.673 V.64 N.W 1.674 V.65 N.W 1.675 V.66 N.W 1.676 V.67 N.W 1.677 V.68 N.W 1.678 V.69 N.W 1.679 V.70 N.W 1.680 V.71 N.W 1.681 V.72 N.W 1.682 V.73 N.W 1.683 V.74 N.W 1.684 V.75 N.W 1.685 V.76 N.W 1.686 V.77 N.W 1.687 V.78 N.W 1.688 V.79 N.W 1.689 V.80 N.W 1.690 V.81 N.W 1.691 V.82 N.W 1.692 V.83 N.W 1.693 V.84 N.W 1.694 V.85 N.W 1.695 V.86 N.W 1.696 V.87 N.W 1.697 V.88 N.W 1.698 V.89 N.W 1.699 V.90 N.W 1.700 V.91 N.W 1.701 V.92 N.W 1.702 V.93 N.W 1.703 V.94 N.W 1.704 V.95 N.W 1.705 V.96 N.W 1.706 V.97 N.W 1.707 V.98 N.W 1.708 V.99 N.W 1.709 V.100 N.W 1.710 V.101 N.W 1.711 V.102 nw 1.712 V.103 N.W 1.713 V.104 N.W 1.714 V.105 N.W 1.715 V.106 N.W 1.716 V.107 N.W 1.717 V.108 N.W 1.718 V.109 N.W 1.719 V.PO N.W 1.720 V.111 N.W

1.721 V.112 N.W 1.722 V.IZ N.W 1.723 V.114 N.W 1.724 V.115 N.W 1.725 V.116 N.W 1.726 V.117 N.W 1.727 V.118 N.W 1.728 V.119 N.W 1.729 V.120 N.W 1.730 V.121 N.W 1.731 V.122 N.W 1.732 V.123 N.W 1.733 V.124 N.W 1.734 V.125 N.W 1.735 V.126 N.W 1.736 V.127 N.W 1.737 V.128 N.W 1.738 V.129 N.W 1.739 V.130 N.W 1.740 V.131 N.W 1.741 V.132 N.W 1.742 V.133 N.W 1.743 V.134 N.W 1.744 V.135 N.W 1.745 V.136 N.W 1.746 V.137 N.W 1.747 V.138 N.W 1.748 V.139 N.W 1.749 V.140 N.W 1.750 V.141 N.W 1.751 V.142 N.W 1.752 V.143 N.W 1.753 V.144 N.W 1.754 V.145 N.W 1.755 V.146 N.W 1.756 V.147 N.W 1.757 V.148 N.W 1.758 V.149 N.W 1.759 V.150 N.W 1.760 V.151 N.W 1.761 V.152 N.W 1.762 V.153 N.W 1.763 V.154 N.W 1.764 V.155 N.W 1.765 V.156 N.W 1.766 V.157 N.W 1.767 V.158 nw 1.768 V.159 N.W 1.769 V.160 N.W 1.770 V.161 N.W 1.771 V.162 N.W 1.772 V.163 N.W 1.773 V.164 N.W 1.774 V.165 N.W 1.775 V.166 N.W 1.776 V.167 N.W

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1.777 V.168 s.z 1.778 V.169 s.z 1.779 V.170 s.z 1.780 V.171 s.z 1.781 V.172 s.z 1.782 V.173 s.z 1.783 V.174 s.z 1.784 V.175 s.z 1.785 V.176 s.z 1.786 V.177 s.z 1.787 V.178 s.z 1.788 V.179 s.z 1.789 V.180 s.z 1.790 V.181 s.z 1.791 V.182 s.z 1.792 V.183 s.z 1.793 V.184 s.z 1.794 V.185 s.z 1.795 V.186 s.z 1.796 V.187 s.z 1.797 V.188 s.z 1.798 V.189 s.z 1.799 V.190 s.z 1.800 V.191 s.z 1.801 V.192 s.z 1.802 V.193 s.z 1.803 V.194 s.z 1.804 V.195 s.z 1.805 V.196 s.z 1.806 V.197 s.z 1.807 V.198 s.z 1.808 V.199 s.z 1.809 V.200 s.z 1.810 V.201 s.z 1.811 V.202 s.z 1.812 V.203 s.z

- 50 044989

1.813 B.l C.4 1.814 B.2 C.4 1.815 V.Z C.4 1.816 B.4 C.4 1.817 AT 5 C.4 1.818 AT 6 C.4 1.819 AT 7 C.4 1.820 AT 8 C.4 1.821 AT 9 C.4 1.822 AT 10 C.4 1.823 IN AND C.4 1.824 AT 12 C.4 1.825 B.13 C.4 1.826 B.14 C.4 1.827 B.15 C.4 1.828 V.16 C.4 1.829 B.17 C.4 1.830 V.18 C.4 1.831 V.19 C.4 1.832 IN 20 C.4 1.833 AT 21 C.4 1.834 V.22 C.4 1.835 V.23 C.4 1.836 V.24 C.4 1.837 V.25 C.4 1.838 V.26 C.4 1.839 V.27 C.4 1.840 V.28 C.4 1.841 V.29 C.4 1.842 V.ZO C.4 1.843 B.31 C.4 1.844 V.32 C.4 1.845 V.ZZ C.4 1.846 V.34 C.4 1.847 V.35 C.4 1.848 V.36 C.4 1.849 V.37 C.4 1.850 V.38 C.4 1.851 V.39 C.4 1.852 B.40 C.4 1.853 V.41 C.4 1.854 V.42 C.4 1.855 V.43 C.4 1.856 V.44 C.4 1.857 V.45 C.4 1.858 V.46 C.4 1.859 V.47 C.4 1.860 V.48 C.4 1.861 V.49 C.4 1.862 V.50 C.4 1.863 V.51 C.4 1.864 V.52 C.4 1.865 V.53 C.4 1.866 V.54 C.4 1.867 V.55 C.4

1.868 V.56 C.4 1.869 V.57 C.4 1.870 V.58. C.4 1.871 V.59 C.4 1.872 B.60 C.4 1.873 V.61 C.4 1.874 V.62 C.4 1.875 V.63 C.4 1.876 V.64 C.4 1.877 V.65 C.4 1.878 V.66 C.4 1.879 V.67 C.4 1.880 V.68 C.4 1.881 V.69 C.4 1.882 V.70 C.4 1.883 V.71 C.4 1.884 V.72 C.4 1.885 V.73 C.4 1.886 V.74 C.4 1.887 V.75 C.4 1.888 V.76 C.4 1.889 V.77 C.4 1.890 V.78 C.4 1.891 V.79 C.4 1.892 V.80 C.4 1.893 V.81 C.4 1.894 V.82 C.4 1.895 V.83 C.4 1.896 V.84 C.4 1.897 V.85 C.4 1.898 V.86 C.4 1.899 V.87 C.4 1.900 V.88 C.4 1.901 V.89 C.4 1.902 V.90 C.4 1.903 V.91 C.4 1.904 V.92 C.4 1.905 V.93 C.4 1.906 V.94 C.4 1.907 V.95 C.4 1.908 V.96 C.4 1.909 V.97 C.4 1.910 V.98 C.4 1.911 V.99 C.4 1.912 V.100 C.4 1.913 V.101 C.4 1.914 V.102 C.4 1.915 V.103 C.4 1.916 V.104 C.4 1.917 V.105 C.4 1.918 V.106 C.4 1.919 V.107 C.4 1.920 V.108 C.4 1.921 V.109 C.4 1.922 V.110 C.4 1.923 V.111 C.4

1.924 V.112 C.4 1.925 V.IZ C.4 1.926 V.114 C.4 1.927 V.115 C.4 1.928 V.116 C.4 1.929 V.117 C.4 1.930 V.118 C.4 1.931 V.119 C.4 1.932 V.120 C.4 1.933 V.121 C.4 1.934 V.122 C.4 1.935 V.123 C.4 1.936 V.124 C.4 1.937 V.125 C.4 1.938 V.126 C.4 1.939 V.127 C.4 1.940 V.128 C.4 1.941 V.129 C.4 1.942 V.130 C.4 1.943 V.131 C.4 1.944 V.132 C.4 1.945 V.133 C.4 1.946 V.134 C.4 1.947 V.135 C.4 1.948 V.136 C.4 1.949 V.137 C.4 1.950 V.138 C.4 1.951 V.139 C.4 1.952 V.140 C.4 1.953 V.141 C.4 1.954 V.142 C.4 1.955 V.143 C.4 1.956 V.144 C.4 1.957 V.145 C.4 1.958 V.146 C.4 1.959 V.147 C.4 1.960 V.148 C.4 1.961 V.149 C.4 1.962 V.150 C.4 1.963 V.151 C.4 1.964 V.152 C.4 1.965 V.153 C.4 1.966 V.154 C.4 1.967 V.155 C.4 1.968 V.156 C.4 1.969 V.157 C.4 1.970 V.158 C.4 1.971 V.159 C.4 1.972 V.160 C.4 1.973 V.161 C.4 1.974 V.162 C.4 1.975 V.163 C.4 1.976 V.164 C.4 1.977 V.165 C.4 1.978 V.166 C.4 1.979 V.167 C.4

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1.980 V.168 C.4 1.981 V.169 C.4 1.982 V.170 C.4 1.983 V.171 C.4 1.984 V.172 C.4 1.985 V.173 C.4 1.986 V.174 C.4 1.987 V.175 C.4 1.988 V.176 C.4 1.989 V.177 C.4 1.990 V.178 C.4 1.991 V.179 C.4 1.992 V.180 C.4 1.993 V.181 C.4 1.994 V.182 C.4 1.995 V.183 C.4 1.996 V.184 C.4 1.997 V.185 C.4 1.998 V.186 C.4 1.999 V.187 C.4 1.1000 V.188 C.4 1.1001 V.189 C.4 1.1002 V.190 C.4 1.1003 V.191 C.4 1.1004 V.192 C.4 1.1005 V.193 C.4 1.1006 V.194 C.4 1.1007 V.195 C.4 1.1008 V.196 C.4 1.1009 V.197 C.4 1.1010 V.198 C.4 1.1011 V.199 C.4 1.1012 V.200 C.4 1.1013 V.201 C.4 1.1014 V.202 C.4 1.1015 V.203 C.4

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1.1071 V.56 C.5 1.1127 V.112 C.5 1.1016 B.l C.5 1.1072 V.57 C.5 1.1128 V.113 C.5 1.1017 B.2 C.5 1.1073 V.58. C.5 1.1129 V.114 C.5 1.1018 V.Z C.5 1.1074 V.59 C.5 1.1130 V.115 C.5 1.1019 B.4 C.5 1.1075 B.60 C.5 1.1131 V.116 C.5 1.1020 AT 5 C.5 1.1076 V.61 C.5 1.1132 V.117 C.5 1.1021 AT 6 C.5 1.1077 V.62 C.5 1.1133 V.118 C.5 1.1022 AT 7 C.5 1.1078 V.63 C.5 1.1134 V.119 C.5 1.1023 AT 8 C.5 1.1079 V.64 C.5 1.1135 V.120 C.5 1.1024 AT 9 C.5 1.1080 V.65 C.5 1.1136 V.121 C.5 1.1025 AT 10 C.5 1.1081 V.66 C.5 1.1137 V.122 C.5 1.1026 AT 11 C.5 1.1082 V.67 C.5 1.1138 V.123 C.5 1.1027 AT 12 C.5 1.1083 V.68 C.5 1.1139 V.124 C.5 1.1028 B.13 C.5 1.1084 V.69 C.5 1.1140 V.125 C.5 1.1029 B.14 C.5 1.1085 V.70 C.5 1.1141 V.126 C.5 1.1030 B.15 C.5 1.1086 V.71 C.5 1.1142 V.127 C.5 1.1031 V.16 C.5 1.1087 V.72 C.5 1.1143 V.128 C.5 1.1032 B.17 C.5 1.1088 V.73 C.5 1.1144 V.129 C.5 1.1033 V.18 C.5 1.1089 V.74 C.5 1.1145 V.130 C.5 1.1034 V.19 C.5 1.1090 V.75 C.5 1.1146 V.131 C.5 1.1035 IN 20 C.5 1.1091 V.76 C.5 1.1147 V.132 C.5 1.1036 AT 21 C.5 1.1092 V.77 C.5 1.1148 V.133 C.5 1.1037 V.22 C.5 1.1093 V.78 C.5 1.1149 V.134 C.5 1.1038 V.23 C.5 1.1094 V.79 C.5 1.1150 V.135 C.5 1.1039 V.24 C.5 1.1095 V.80 C.5 1.1151 V.136 C.5 1.1040 V.25 C.5 1.1096 V.81 C.5 1.1152 V.137 C.5 1.1041 V.26 C.5 1.1097 V.82 C.5 1.1153 V.138 C.5 1.1042 V.27 C.5 1.1098 V.83 C.5 1.1154 V.139 C.5 1.1043 V.28 C.5 1.1099 V.84 C.5 1.1155 V.140 C.5 1.1044 V.29 C.5 1.1100 V.85 C.5 1.1156 V.141 C.5 1.1045 V.ZO C.5 1.1101 V.86 C.5 1.1157 V.142 C.5 1.1046 B.31 C.5 1.1102 V.87 C.5 1.1158 V.143 C.5 1.1047 V.32 C.5 1.1103 V.88 C.5 1.1159 V.144 C.5 1.1048 V.ZZ C.5 1.1104 V.89 C.5 1.1160 V.145 C.5 1.1049 V.34 C.5 1.1105 V.90 C.5 1.1161 V.146 C.5 1.1050 V.35 C.5 1.1106 V.91 C.5 1.1162 V.147 C.5 1.1051 V.36 C.5 1.1107 V.92 C.5 1.1163 V.148 C.5 1.1052 V.37 C.5 1.1108 V.93 C.5 1.1164 V.149 C.5 1.1053 V.38 C.5 1.1109 V.94 C.5 1.1165 V.150 C.5 1.1054 V.39 C.5 1.1110 V.95 C.5 1.1166 V.151 C.5 1.1055 B.40 C.5 1.1111 V.96 C.5 1.1167 V.152 C.5 1.1056 V.41 C.5 1.1112 V.97 C.5 1.1168 V.153 C.5 1.1057 V.42 C.5 1.1113 V.98 C.5 1.1169 V.154 C.5 1.1058 V.43 C.5 1.1114 V.99 C.5 1.1170 V.155 C.5 1.1059 V.44 C.5 1.1115 V.100 C.5 1.1171 V.156 C.5 1.1060 V.45 C.5 1.1116 V.101 C.5 1.1172 V.157 C.5 1.1061 V.46 C.5 1.1117 V. 102 C.5 1.1173 V.158 C.5 1.1062 V.47 C.5 1.1118 V.103 C.5 1.1174 V.159 C.5 1.1063 V.48 C.5 1.1119 V. 104 C.5 1.1175 V.160 C.5 1.1064 V.49 C.5 1.1120 V.105 C.5 1.1176 V.161 C.5 1.1065 V.50 C.5 1.1121 V.106 C.5 1.1177 V.162 C.5 1.1066 V.51 C.5 1.1122 V.107 C.5 1.1178 V.163 C.5 1.1067 V.52 C.5 1.1123 V.108 C.5 1.1179 V.164 C.5 1.1068 V.53 C.5 1.1124 V.109 C.5 1.1180 V.165 C.5 1.1069 V.54 C.5 1.1125 V.110 C.5 1.1181 V.166 C.5 1.1070 V.55 C.5 1.1126 V.111 C.5 1.1182 V.167 C.5

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1.1183 V.168 C.5 1.1184 V.169 C.5 1.1185 V.170 C.5 1.1186 V.171 C.5 1.1187 V.172 C.5 1.1188 V.173 C.5 1.1189 V.174 C.5 1.1190 V.175 C.5 1.1191 V.176 C.5 1.1192 V.177 C.5 1.1193 V.178 C.5 1.1194 V.179 C.5 1.1195 V.180 C.5 1.1196 V.181 C.5 1.1197 V.182 C.5 1.1198 V.183 C.5 1.1199 V.184 C.5 1.1200 V.185 C.5 1.1201 V.186 C.5 1.1202 V.187 C.5 1.1203 V.188 C.5 1.1204 V.189 C.5 1.1205 V.190 C.5 1.1206 V.191 C.5 1.1207 V.192 C.5 1.1208 V.193 C.5 1.1209 V.194 C.5 1.1210 V.195 C.5 1.1211 V.196 C.5 1.1212 V.197 C.5 1.1213 V.198 C.5 1.1214 V.199 C.5 1.1215 V.200 C.5 1.1216 V.201 C.5 1.1217 V.202 C.5 1.1218 V.203 C.5

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1.1219 IN 1 C.6 1.1220 AT 2 C.6 1.1221 V.Z C.6 1.1222 AT 4 C.6 1.1223 AT 5 C.6 1.1224 AT 6 C.6 1.1225 AT 7 C.6 1.1226 AT 8 C.6 1.1227 AT 9 C.6 1.1228 AT 10 C.6 1.1229 IN AND C.6 1.1230 AT 12 C.6 1.1231 B.13 C.6 1.1232 B.14 C.6 1.1233 B.15 C.6 1.1234 V.16 C.6 1.1235 B.17 C.6 1.1236 V.18 C.6 1.1237 V.19 C.6 1.1238 IN 20 C.6 1.1239 AT 21 C.6 1.1240 V.22 C.6 1.1241 V.23 C.6 1.1242 V.24 C.6 1.1243 V.25 C.6 1.1244 V.26 C.6 1.1245 V.27 C.6 1.1246 V.28 C.6 1.1247 V.29 C.6 1.1248 V.ZO C.6 1.1249 B.31 C.6 1.1250 V.32 C.6 1.1251 V.ZZ C.6 1.1252 V.34 C.6 1.1253 V.35 C.6 1.1254 V.36 C.6 1.1255 V.37 C.6 1.1256 V.38 C.6 1.1257 V.39 C.6 1.1258 B.40 C.6 1.1259 V.41 C.6 1.1260 V.42 C.6 1.1261 V.43 C.6 1.1262 V.44 C.6 1.1263 V.45 C.6 1.1264 V.46 C.6 1.1265 V.47 C.6 1.1266 V.48 C.6 1.1267 V.49 C.6 1.1268 V.50 C.6 1.1269 V.51 C.6 1.1270 V.52 C.6 1.1271 V.53 C.6 1.1272 V.54 C.6 1.1273 V.55 C.6

1.1274 V.56 C.6 1.1275 V.57 C.6 1.1276 V.58. C.6 1.1277 V.59 C.6 1.1278 B.60 C.6 1.1279 V.61 C.6 1.1280 V.62 C.6 1.1281 V.63 C.6 1.1282 V.64 C.6 1.1283 V.65 C.6 1.1284 V.66 C.6 1.1285 V.67 C.6 1.1286 V.68 C.6 1.1287 V.69 C.6 1.1288 V.70 C.6 1.1289 V.71 C.6 1.1290 V.72 C.6 1.1291 V.73 C.6 1.1292 V.74 C.6 1.1293 V.75 C.6 1.1294 V.76 C.6 1.1295 V.77 C.6 1.1296 V.78 C.6 1.1297 V.79 C.6 1.1298 V.80 C.6 1.1299 V.81 C.6 1.1300 V.82 C.6 1.1301 V.83 C.6 1.1302 V.84 C.6 1.1303 V.85 C.6 1.1304 V.86 C.6 1.1305 V.87 C.6 1.1306 V.88 C.6 1.1307 V.89 C.6 1.1308 V.90 C.6 1.1309 V.91 C.6 1.1310 V.92 C.6 1.1311 V.93 C.6 1.1312 V.94 C.6 1.1313 V.95 C.6 1.1314 V.96 C.6 1.1315 V.97 C.6 1.1316 V.98 C.6 1.1317 V.99 C.6 1.1318 V.100 C.6 1.1319 V.101 C.6 1.1320 V. 102 C.6 1.1321 V.103 C.6 1.1322 V. 104 C.6 1.1323 V.105 C.6 1.1324 V.106 C.6 1.1325 V.107 C.6 1.1326 V.108 C.6 1.1327 V.109 C.6 1.1328 V.110 C.6 1.1329 V.111 C.6

1.1330 V.112 C.6 1.1331 V.IZ C.6 1.1332 V.114 C.6 1.1333 V.115 C.6 1.1334 V.116 C.6 1.1335 V.117 C.6 1.1336 V.118 C.6 1.1337 V.119 C.6 1.1338 V.120 C.6 1.1339 V.121 C.6 1.1340 V.122 C.6 1.1341 V.123 C.6 1.1342 V.124 C.6 1.1343 V.125 C.6 1.1344 V.126 C.6 1.1345 V.127 C.6 1.1346 V.128 C.6 1.1347 V.129 C.6 1.1348 V.130 C.6 1.1349 V.131 C.6 1.1350 V.132 C.6 1.1351 V.133 C.6 1.1352 V.134 C.6 1.1353 V.135 C.6 1.1354 V.136 C.6 1.1355 V.137 C.6 1.1356 V.138 C.6 1.1357 V.139 C.6 1.1358 V.140 C.6 1.1359 V.141 C.6 1.1360 V.142 C.6 1.1361 V.143 C.6 1.1362 V.144 C.6 1.1363 V.145 C.6 1.1364 V.146 C.6 1.1365 V.147 C.6 1.1366 V.148 C.6 1.1367 V.149 C.6 1.1368 V.150 C.6 1.1369 V.151 C.6 1.1370 V.152 C.6 1.1371 V.153 C.6 1.1372 V.154 C.6 1.1373 V.155 C.6 1.1374 V.156 C.6 1.1375 V.157 C.6 1.1376 V.158 C.6 1.1377 V.159 C.6 1.1378 V.160 C.6 1.1379 V.161 C.6 1.1380 V.162 C.6 1.1381 V.163 C.6 1.1382 V.164 C.6 1.1383 V.165 C.6 1.1384 V.166 C.6 1.1385 V.167 C.6

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1.1386 V.168 C.6 1.1387 V.169 C.6 1.1388 V.170 C.6 1.1389 V.171 C.6 1.1390 V.172 C.6 1.1391 V.173 C.6 1.1392 V.174 C.6 1.1393 V.175 C.6 1.1394 V.176 C.6 1.1395 V.177 C.6 1.1396 V.178 C.6 1.1397 V.179 C.6 1.1398 V.180 C.6 1.1399 V.181 C.6 1.1400 V.182 C.6 1.1401 V.183 C.6 1.1402 V.184 C.6 1.1403 V.185 C.6 1.1404 V.186 C.6 1.1405 V.187 C.6 1.1406 V.188 C.6 1.1407 V.189 C.6 1.1408 V.190 C.6 1.1409 V.191 C.6 1.1410 V.192 C.6 1.1411 V.193 C.6 1.1412 V.194 C.6 1.1413 V.195 C.6 1.1414 V.196 C.6 1.1415 V.197 C.6 1.1416 V.198 C.6 1.1417 V.199 C.6 1.1418 V.200 C.6 1.1419 V.201 C.6 1.1420 V.202 C.6 1.1421 V.203 C.6

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1.1422 B.l P.7 1.1423 B.2 P.7 1.1424 V.Z P.7 1.1425 B.4 P.7 1.1426 AT 5 P.7 1.1427 AT 6 P.7 1.1428 AT 7 P.7 1.1429 AT 8 P.7 1.1430 AT 9 P.7 1.1431 AT 10 P.7 1.1432 IN AND P.7 1.1433 AT 12 P.7 1.1434 B.13 P.7 1.1435 B.14 P.7 1.1436 B.15 P.7 1.1437 V.16 P.7 1.1438 B.17 P.7 1.1439 V.18 P.7 1.1440 V.19 P.7 1.1441 IN 20 P.7 1.1442 AT 21 P.7 1.1443 V.22 P.7 1.1444 V.23 P.7 1.1445 V.24 P.7 1.1446 V.25 P.7 1.1447 V.26 P.7 1.1448 V.27 P.7 1.1449 V.28 P.7 1.1450 V.29 P.7 1.1451 V.ZO P.7 1.1452 B.31 P.7 1.1453 V.32 P.7 1.1454 V.ZZ P.7 1.1455 V.34 P.7 1.1456 V.35 P.7 1.1457 V.36 P.7 1.1458 V.37 P.7 1.1459 V.38 P.7 1.1460 V.39 P.7 1.1461 B.40 P.7 1.1462 V.41 P.7 1.1463 V.42 P.7 1.1464 V.43 P.7 1.1465 V.44 P.7 1.1466 V.45 P.7 1.1467 V.46 P.7 1.1468 V.47 P.7 1.1469 V.48 P.7 1.1470 V.49 P.7 1.1471 V.50 P.7 1.1472 V.51 P.7 1.1473 V.52 P.7 1.1474 V.53 P.7 1.1475 V.54 P.7 1.1476 V.55 P.7

1.1477 V.56 P.7 1.1478 V.57 P.7 1.1479 V.58. P.7 1.1480 V.59 P.7 1.1481 B.60 P.7 1.1482 V.61 P.7 1.1483 V.62 P.7 1.1484 V.63 P.7 1.1485 V.64 P.7 1.1486 V.65 P.7 1.1487 V.66 P.7 1.1488 V.67 P.7 1.1489 V.68 P.7 1.1490 V.69 P.7 1.1491 V.70 P.7 1.1492 V.71 P.7 1.1493 V.72 P.7 1.1494 V.73 P.7 1.1495 V.74 P.7 1.1496 V.75 P.7 1.1497 V.76 P.7 1.1498 V.77 P.7 1.1499 V.78 P.7 1.1500 V.79 P.7 1.1501 V.80 P.7 1.1502 V.81 P.7 1.1503 V.82 P.7 1.1504 V.83 P.7 1.1505 V.84 P.7 1.1506 V.85 P.7 1.1507 V.86 P.7 1.1508 V.87 P.7 1.1509 V.88 P.7 1.1510 V.89 P.7 1.1511 V.90 P.7 1.1512 V.91 P.7 1.1513 V.92 P.7 1.1514 V.93 P.7 1.1515 V.94 P.7 1.1516 V.95 P.7 1.1517 V.96 P.7 1.1518 V.97 P.7 1.1519 V.98 P.7 1.1520 V.99 P.7 1.1521 V.100 P.7 1.1522 V.101 P.7 1.1523 V. 102 P.7 1.1524 V.103 P.7 1.1525 V. 104 P.7 1.1526 V.105 P.7 1.1527 V.106 P.7 1.1528 V.107 P.7 1.1529 V.108 P.7 1.1530 V.109 P.7 1.1531 V.110 P.7 1.1532 V.111 P.7

1.1533 V.112 P.7 1.1534 V.IZ P.7 1.1535 V.114 P.7 1.1536 V.115 P.7 1.1537 V.116 P.7 1.1538 V.117 P.7 1.1539 V.118 P.7 1.1540 V.119 P.7 1.1541 V.120 P.7 1.1542 V.121 P.7 1.1543 V.122 P.7 1.1544 V.123 P.7 1.1545 V.124 P.7 1.1546 V.125 P.7 1.1547 V.126 P.7 1.1548 V.127 P.7 1.1549 V.128 P.7 1.1550 V.129 P.7 1.1551 V.130 P.7 1.1552 V.131 P.7 1.1553 V.132 P.7 1.1554 V.133 P.7 1.1555 V.134 P.7 1.1556 V.135 P.7 1.1557 V.136 P.7 1.1558 V.137 P.7 1.1559 V.138 P.7 1.1560 V.139 P.7 1.1561 V.140 P.7 1.1562 V.141 P.7 1.1563 V.142 P.7 1.1564 V.143 P.7 1.1565 V.144 P.7 1.1566 V.145 P.7 1.1567 V.146 P.7 1.1568 V.147 P.7 1.1569 V.148 P.7 1.1570 V.149 P.7 1.1571 V.150 P.7 1.1572 V.151 P.7 1.1573 V.152 P.7 1.1574 V.153 P.7 1.1575 V.154 P.7 1.1576 V.155 P.7 1.1577 V.156 P.7 1.1578 V.157 P.7 1.1579 V.158 P.7 1.1580 V.159 P.7 1.1581 V.160 P.7 1.1582 V.161 P.7 1.1583 V.162 P.7 1.1584 V.163 P.7 1.1585 V.164 P.7 1.1586 V.165 P.7 1.1587 V.166 P.7 1.1588 V.167 P.7

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1.1589 V.168 P.7 1.1590 V.169 P.7 1.1591 V.170 P.7 1.1592 V.171 P.7 1.1593 V.172 P.7 1.1594 V.173 P.7 1.1595 V.174 P.7 1.1596 V.175 P.7 1.1597 V.176 P.7 1.1598 V.177 P.7 1.1599 V.178 P.7 1.1600 V.179 P.7 1.1601 V.180 P.7 1.1602 V.181 P.7 1.1603 V.182 P.7 1.1604 V.183 P.7 1.1605 V.184 P.7 1.1606 V.185 P.7 1.1607 V.186 P.7 1.1608 V.187 P.7 1.1609 V.188 P.7 1.1610 V.189 P.7 1.1611 V.190 P.7 1.1612 V.191 P.7 1.1613 V.192 P.7 1.1614 V.193 P.7 1.1615 V.194 P.7 1.1616 V.195 P.7 1.1617 V.196 P.7 1.1618 V.197 P.7 1.1619 V.198 P.7 1.1620 V.199 P.7 1.1621 V.200 P.7 1.1622 V.201 P.7 1.1623 V.202 P.7 1.1624 V.203 P.7

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1.1680 V.56 P.8 1.1736 V.112 P.8 1.1625 B.l P.8 1.1681 V.57 P.8 1.1737 V.IZ P.8 1.1626 B.2 P.8 1.1682 V.58. P.8 1.1738 V.114 P.8 1.1627 V.Z P.8 1.1683 V.59 P.8 1.1739 V.115 P.8 1.1628 B.4 P.8 1.1684 B.60 P.8 1.1740 V.116 P.8 1.1629 AT 5 P.8 1.1685 V.61 P.8 1.1741 V.117 P.8 1.1630 AT 6 P.8 1.1686 V.62 P.8 1.1742 V.118 P.8 1.1631 AT 7 P.8 1.1687 V.63 P.8 1.1743 V.119 P.8 1.1632 AT 8 P.8 1.1688 V.64 P.8 1.1744 V.120 P.8 1.1633 AT 9 P.8 1.1689 V.65 P.8 1.1745 V.121 P.8 1.1634 AT 10 P.8 1.1690 V.66 P.8 1.1746 V.122 P.8 1.1635 IN AND P.8 1.1691 V.67 P.8 1.1747 V.123 P.8 1.1636 AT 12 P.8 1.1692 V.68 P.8 1.1748 V.124 P.8 1.1637 B.13 P.8 1.1693 V.69 P.8 1.1749 V.125 P.8 1.1638 B.14 P.8 1.1694 V.70 P.8 1.1750 V.126 P.8 1.1639 B.15 P.8 1.1695 V.71 P.8 1.1751 V.127 P.8 1.1640 V.16 P.8 1.1696 V.72 P.8 1.1752 V.128 P.8 1.1641 B.17 P.8 1.1697 V.73 P.8 1.1753 V.129 P.8 1.1642 V.18 P.8 1.1698 V.74 P.8 1.1754 V.130 P.8 1.1643 V.19 P.8 1.1699 V.75 P.8 1.1755 V.131 P.8 1.1644 IN 20 P.8 1.1700 V.76 P.8 1.1756 V.132 P.8 1.1645 AT 21 P.8 1.1701 V.77 P.8 1.1757 V.133 P.8 1.1646 V.22 P.8 1.1702 V.78 P.8 1.1758 V.134 P.8 1.1647 V.23 P.8 1.1703 V.79 P.8 1.1759 V.135 P.8 1.1648 V.24 P.8 1.1704 V.80 P.8 1.1760 V.136 P.8 1.1649 V.25 P.8 1.1705 V.81 P.8 1.1761 V.137 P.8 1.1650 V.26 P.8 1.1706 V.82 P.8 1.1762 V.138 P.8 1.1651 V.27 P.8 1.1707 V.83 P.8 1.1763 V.139 P.8 1.1652 V.28 P.8 1.1708 V.84 P.8 1.1764 V.140 P.8 1.1653 V.29 P.8 1.1709 V.85 P.8 1.1765 V.141 P.8 1.1654 V.ZO P.8 1.1710 V.86 P.8 1.1766 V.142 P.8 1.1655 B.31 P.8 1.1711 V.87 P.8 1.1767 V.143 P.8 1.1656 V.32 P.8 1.1712 V.88 P.8 1.1768 V.144 P.8 1.1657 V.ZZ P.8 1.1713 V.89 P.8 1.1769 V.145 P.8 1.1658 V.34 P.8 1.1714 V.90 P.8 1.1770 V.146 P.8 1.1659 V.35 P.8 1.1715 V.91 P.8 1.1771 V.147 P.8 1.1660 V.36 P.8 1.1716 V.92 P.8 1.1772 V.148 P.8 1.1661 V.37 P.8 1.1717 V.93 P.8 1.1773 V.149 P.8 1.1662 V.38 P.8 1.1718 V.94 P.8 1.1774 V.150 P.8 1.1663 V.39 P.8 1.1719 V.95 P.8 1.1775 V.151 P.8 1.1664 B.40 P.8 1.1720 V.96 P.8 1.1776 V.152 P.8 1.1665 V.41 P.8 1.1721 V.97 P.8 1.1777 V.153 P.8 1.1666 V.42 P.8 1.1722 V.98 P.8 1.1778 V.154 P.8 1.1667 VAZ P.8 1.1723 V.99 P.8 1.1779 V.155 P.8 1.1668 V.44 P.8 1.1724 V.100 P.8 1.1780 V.156 P.8 1.1669 V.45 P.8 1.1725 V.101 P.8 1.1781 V.157 P.8 1.1670 B.46 P.8 1.1726 V.102 P.8 1.1782 V.158 P.8 1.1671 V.47 P.8 1.1727 V.103 P.8 1.1783 V.159 P.8 1.1672 V.48 P.8 1.1728 V.104 P.8 1.1784 V.160 P.8 1.1673 V.49 P.8 1.1729 V.105 P.8 1.1785 V.161 P.8 1.1674 V.50 P.8 1.1730 V.106 P.8 1.1786 V.162 P.8 1.1675 V.51 P.8 1.1731 V.107 P.8 1.1787 V.163 P.8 1.1676 V.52 P.8 1.1732 V.108 P.8 1.1788 V.164 P.8 1.1677 V.53 P.8 1.1733 V.109 P.8 1.1789 V.165 P.8 1.1678 V.54 P.8 1.1734 V.110 P.8 1.1790 V.166 P.8 1.1679 V.55 P.8 1.1735 V.111 P.8 1.1791 V.167 P.8

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1.1792 V.168 P.8 1.1793 V.169 P.8 1.1794 V.170 P.8 1.1795 V.171 P.8 1.1796 V.172 P.8 1.1797 V.173 P.8 1.1798 V.174 P.8 1.1799 V.175 P.8 1.1800 V.176 P.8 1.1801 V.177 P.8 1.1802 V.178 P.8 1.1803 V.179 P.8 1.1804 V.180 P.8 1.1805 V.181 P.8 1.1806 V.182 P.8 1.1807 V.183 P.8 1.1808 V.184 P.8 1.1809 V.185 P.8 1.1810 V.186 P.8 1.1811 V.187 P.8 1.1812 V.188 P.8 1.1813 V.189 P.8 1.1814 V.190 P.8 1.1815 V.191 P.8 1.1816 V.192 P.8 1.1817 V.193 P.8 1.1818 V.194 P.8 1.1819 V.195 P.8 1.1820 V.196 P.8 1.1821 V.197 P.8 1.1822 V.198 P.8 1.1823 V.199 P.8 1.1824 V.200 P.8 1.1825 V.201 P.8 1.1826 V.202 P.8 1.1827 V.203 P.8

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1.1883 V.56 P.9 1.1939 V.112 P.9 1.1828 B.l P.9 1.1884 V.57 P.9 1.1940 V.IZ P.9 1.1829 B.2 P.9 1.1885 V.58. P.9 1.1941 V.114 P.9 1.1830 V.Z P.9 1.1886 V.59 P.9 1.1942 V.115 P.9 1.1831 B.4 P.9 1.1887 B.60 P.9 1.1943 V.116 P.9 1.1832 AT 5 P.9 1.1888 V.61 P.9 1.1944 V.117 P.9 1.1833 AT 6 P.9 1.1889 V.62 P.9 1.1945 V.118 P.9 1.1834 AT 7 P.9 1.1890 V.63 P.9 1.1946 V.119 P.9 1.1835 AT 8 P.9 1.1891 V.64 P.9 1.1947 V.120 P.9 1.1836 AT 9 P.9 1.1892 V.65 P.9 1.1948 V.121 P.9 1.1837 AT 10 P.9 1.1893 V.66 P.9 1.1949 V.122 P.9 1.1838 AT 11 P.9 1.1894 V.67 P.9 1.1950 V.123 P.9 1.1839 AT 12 P.9 1.1895 V.68 P.9 1.1951 V.124 P.9 1.1840 B.13 P.9 1.1896 V.69 P.9 1.1952 V.125 P.9 1.1841 B.14 P.9 1.1897 V.70 P.9 1.1953 V.126 P.9 1.1842 B.15 P.9 1.1898 V.71 P.9 1.1954 V.127 P.9 1.1843 V.16 P.9 1.1899 V.72 P.9 1.1955 V.128 P.9 1.1844 B.17 P.9 1.1900 V.73 P.9 1.1956 V.129 P.9 1.1845 V.18 P.9 1.1901 V.74 P.9 1.1957 V.130 P.9 1.1846 V.19 P.9 1.1902 V.75 P.9 1.1958 V.131 P.9 1.1847 IN 20 P.9 1.1903 V.76 P.9 1.1959 V.132 P.9 1.1848 AT 21 P.9 1.1904 V.77 P.9 1.1960 V.133 P.9 1.1849 V.22 P.9 1.1905 V.78 P.9 1.1961 V.134 P.9 1.1850 V.23 P.9 1.1906 V.79 P.9 1.1962 V.135 P.9 1.1851 V.24 P.9 1.1907 V.80 P.9 1.1963 V.136 P.9 1.1852 V.25 P.9 1.1908 V.81 P.9 1.1964 V.137 P.9 1.1853 V.26 P.9 1.1909 V.82 P.9 1.1965 V.138 P.9 1.1854 V.27 P.9 1.1910 V.83 P.9 1.1966 V.139 P.9 1.1855 V.28 P.9 1.1911 V.84 P.9 1.1967 V.140 P.9 1.1856 V.29 P.9 1.1912 V.85 P.9 1.1968 V.141 P.9 1.1857 V.ZO P.9 1.1913 V.86 P.9 1.1969 V.142 P.9 1.1858 B.31 P.9 1.1914 V.87 P.9 1.1970 V.143 P.9 1.1859 V.32 P.9 1.1915 V.88 P.9 1.1971 V.144 P.9 1.1860 V.ZZ P.9 1.1916 V.89 P.9 1.1972 V.145 P.9 1.1861 V.34 P.9 1.1917 V.90 P.9 1.1973 V.146 P.9 1.1862 V.35 P.9 1.1918 V.91 P.9 1.1974 V.147 P.9 1.1863 V.36 P.9 1.1919 V.92 P.9 1.1975 V.148 P.9 1.1864 V.37 P.9 1.1920 V.93 P.9 1.1976 V.149 P.9 1.1865 V.38 P.9 1.1921 V.94 P.9 1.1977 V.150 P.9 1.1866 V.39 P.9 1.1922 V.95 P.9 1.1978 V.151 P.9 1.1867 B.40 P.9 1.1923 V.96 P.9 1.1979 V.152 P.9 1.1868 V.41 P.9 1.1924 V.97 P.9 1.1980 V.153 P.9 1.1869 V.42 P.9 1.1925 V.98 P.9 1.1981 V.154 P.9 1.1870 V.43 P.9 1.1926 V.99 P.9 1.1982 V.155 P.9 1.1871 V.44 P.9 1.1927 V.100 P.9 1.1983 V.156 P.9 1.1872 V.45 P.9 1.1928 V.101 P.9 1.1984 V.157 P.9 1.1873 B.46 P.9 1.1929 V.102 P.9 1.1985 V.158 P.9 1.1874 V.47 P.9 1.1930 V.103 P.9 1.1986 V.159 P.9 1.1875 V.48 P.9 1.1931 V. 104 P.9 1.1987 V.160 P.9 1.1876 V.49 P.9 1.1932 V.105 P.9 1.1988 V.161 P.9 1.1877 V.50 P.9 1.1933 V.106 P.9 1.1989 V.162 P.9 1.1878 V.51 P.9 1.1934 V.107 P.9 1.1990 V.163 P.9 1.1879 V.52 P.9 1.1935 V.108 P.9 1.1991 V.164 P.9 1.1880 V.53 P.9 1.1936 V.109 P.9 1.1992 V.165 P.9 1.1881 V.54 P.9 1.1937 V.PO P.9 1.1993 V.166 P.9 1.1882 V.55 P.9 1.1938 V.111 P.9 1.1994 V.167 P.9

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1.1995 V.168 P.9 1.1996 V.169 P.9 1.1997 V.170 P.9 1.1998 V.171 P.9 1.1999 V.172 P.9 1.2000 V.173 P.9 1.2001 V.174 P.9 1.2002 V.175 P.9 1.2003 V.176 P.9 1.2004 V.177 P.9 1.2005 V.178 P.9 1.2006 V.179 P.9 1.2007 V.180 P.9 1.2008 V.181 P.9 1.2009 V.182 P.9 1.2010 V.183 P.9 1.2011 V.184 P.9 1.2012 V.185 P.9 1.2013 V.186 P.9 1.2014 V.187 P.9 1.2015 V.188 P.9 1.2016 V.189 P.9 1.2017 V.190 P.9 1.2018 V.191 P.9 1.2019 V.192 P.9 1.2020 V.193 P.9 1.2021 V.194 P.9 1.2022 V.195 P.9 1.2023 V.196 P.9 1.2024 V.197 P.9 1.2025 V.198 P.9 1.2026 V.199 P.9 1.2027 V.200 P.9 1.2028 V.201 P.9 1.2029 V.202 P.9 1.2030 V.203 P.9

- 62 044989

1.2086 V.56 P.10 1.2142 V.112 P.10 1.2031 IN 1 P.10 1.2087 V.57 P.10 1.2143 V.IZ P.10 1.2032 AT 2 P.10 1.2088 V.58. P.10 1.2144 V.114 P.10 1.2033 V.Z P.10 1.2089 V.59 P.10 1.2145 V.115 P.10 1.2034 AT 4 P.10 1.2090 B.60 P.10 1.2146 V.116 P.10 1.2035 AT 5 P.10 1.2091 V.61 P.10 1.2147 V.117 P.10 1.2036 AT 6 P.10 1.2092 V.62 P.10 1.2148 V.118 P.10 1.2037 AT 7 P.10 1.2093 V.63 P.10 1.2149 V.119 P.10 1.2038 AT 8 P.10 1.2094 V.64 P.10 1.2150 V.120 P.10 1.2039 AT 9 P.10 1.2095 V.65 P.10 1.2151 V.121 P.10 1.2040 AT 10 P.10 1.2096 V.66 P.10 1.2152 V.122 P.10 1.2041 IN AND P.10 1.2097 V.67 P.10 1.2153 V.123 P.10 1.2042 AT 12 P.10 1.2098 V.68 P.10 1.2154 V.124 P.10 1.2043 B.13 P.10 1.2099 V.69 P.10 1.2155 V.125 P.10 1.2044 B.14 P.10 1.2100 V.70 P.10 1.2156 V.126 P.10 1.2045 B.15 P.10 1.2101 V.71 P.10 1.2157 V.127 P.10 1.2046 V.16 P.10 1.2102 V.72 P.10 1.2158 V.128 P.10 1.2047 B.17 P.10 1.2103 V.73 P.10 1.2159 V.129 P.10 1.2048 V.18 P.10 1.2104 V.74 P.10 1.2160 V.130 P.10 1.2049 V.19 P.10 1.2105 V.75 P.10 1.2161 V.131 P.10 1.2050 IN 20 P.10 1.2106 V.76 P.10 1.2162 V.132 P.10 1.2051 AT 21 P.10 1.2107 V.77 P.10 1.2163 V.133 P.10 1.2052 V.22 P.10 1.2108 V.78 P.10 1.2164 V.134 P.10 1.2053 V.23 P.10 1.2109 V.79 P.10 1.2165 V.135 P.10 1.2054 V.24 P.10 1.2110 V.80 P.10 1.2166 V.136 P.10 1.2055 V.25 P.10 1.2111 V.81 P.10 1.2167 V.137 P.10 1.2056 V.26 P.10 1.2112 V.82 P.10 1.2168 V.138 P.10 1.2057 V.27 P.10 1.2113 V.83 P.10 1.2169 V.139 P.10 1.2058 V.28 P.10 1.2114 V.84 P.10 1.2170 V.140 P.10 1.2059 V.29 P.10 1.2115 V.85 P.10 1.2171 V.141 P.10 1.2060 V.ZO P.10 1.2116 V.86 P.10 1.2172 V.142 P.10 1.2061 B.31 P.10 1.2117 V.87 P.10 1.2173 V.143 P.10 1.2062 V.32 P.10 1.2118 V.88 P.10 1.2174 V.144 P.10 1.2063 V.ZZ P.10 1.2119 V.89 P.10 1.2175 V.145 P.10 1.2064 V.34 P.10 1.2120 V.90 P.10 1.2176 V.146 P.10 1.2065 V.35 P.10 1.2121 V.91 P.10 1.2177 V.147 P.10 1.2066 V.36 P.10 1.2122 V.92 P.10 1.2178 V.148 P.10 1.2067 V.37 P.10 1.2123 V.93 P.10 1.2179 V.149 P.10 1.2068 V.38 P.10 1.2124 V.94 P.10 1.2180 V.150 P.10 1.2069 V.39 P.10 1.2125 V.95 P.10 1.2181 V.151 P.10 1.2070 B.40 P.10 1.2126 V.96 P.10 1.2182 V.152 P.10 1.2071 V.41 P.10 1.2127 V.97 P.10 1.2183 V.153 P.10 1.2072 V.42 P.10 1.2128 V.98 P.10 1.2184 V.154 P.10 1.2073 V.43 P.10 1.2129 V.99 P.10 1.2185 V.155 P.10 1.2074 V.44 P.10 1.2130 V.100 P.10 1.2186 V.156 P.10 1.2075 V.45 P.10 1.2131 V.101 P.10 1.2187 V.157 P.10 1.2076 B.46 P.10 1.2132 V.102 P.10 1.2188 V.158 P.10 1.2077 V.47 P.10 1.2133 V.103 P.10 1.2189 V.159 P.10 1.2078 V.48 P.10 1.2134 V.104 P.10 1.2190 V.160 P.10 1.2079 V.49 P.10 1.2135 V.105 P.10 1.2191 V.161 P.10 1.2080 V.50 P.10 1.2136 V.106 P.10 1.2192 V.162 P.10 1.2081 V.51 P.10 1.2137 V.107 P.10 1.2193 V.163 P.10 1.2082 V.52 P.10 1.2138 V.108 P.10 1.2194 V.164 P.10 1.2083 V.53 P.10 1.2139 V.109 P.10 1.2195 V.165 P.10 1.2084 V.54 P.10 1.2140 V.110 P.10 1.2196 V.166 P.10 1.2085 V.55 P.10 1.2141 V.111 P.10 1.2197 V.167 P.10

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1.2198 V.168 P.10 1.2199 V.169 P.10 1.2200 V.170 P.10 1.2201 V.171 P.10 1.2202 V.172 P.10 1.2203 V.173 P.10 1.2204 V.174 P.10 1.2205 V.175 P.10 1.2206 V.176 P.10 1.2207 V.177 P.10 1.2208 V.178 P.10 1.2209 V.179 P.10 1.2210 V.180 P.10 1.2211 V.181 P.10 1.2212 V.182 P.10 1.2213 V.183 P.10 1.2214 V.184 P.10 1.2215 V.185 P.10 1.2216 V.186 P.10 1.2217 V.187 P.10 1.2218 V.188 P.10 1.2219 V.189 P.10 1.2220 V.190 P.10 1.2221 V.191 P.10 1.2222 V.192 P.10 1.2223 V.193 P.10 1.2224 V.194 P.10 1.2225 V.195 P.10 1.2226 V.196 P.10 1.2227 V.197 P.10 1.2228 V.198 P.10 1.2229 V.199 P.10 1.2230 V.200 P.10 1.2231 V.201 P.10 1.2232 V.202 P.10 1.2233 V.203 P.10

- 64 044989

1.2289 V.56 S.I 1.2345 V.112 P.11 1.2234 B.l P.11 1.2290 V.57 S.I 1.2346 V.IZ P.11 1.2235 B.2 P.11 1.2291 V.58. S.I 1.2347 V.114 P.11 1.2236 V.Z P.11 1.2292 V.59 s.i 1.2348 V.115 P.11 1.2237 B.4 P.11 1.2293 B.60 P.11 1.2349 V.116 P.11 1.2238 AT 5 P.11 1.2294 V.61 s.i 1.2350 V.117 P.11 1.2239 AT 6 P.11 1.2295 V.62 s.i 1.2351 V.118 P.11 1.2240 AT 7 P.11 1.2296 V.63 s.i 1.2352 V.119 P.11 1.2241 AT 8 P.11 1.2297 V.64 s.i 1.2353 V.120 P.11 1.2242 AT 9 P.11 1.2298 V.65 P.11 1.2354 V.121 P.11 1.2243 AT 10 P.11 1.2299 V.66 s.i 1.2355 V.122 P.11 1.2244 IN AND P.11 1.2300 V.67 s.i 1.2356 V.123 P.11 1.2245 AT 12 P.11 1.2301 V.68 s.i 1.2357 V.124 P.11 1.2246 B.13 P.11 1.2302 V.69 s.i 1.2358 V.125 P.11 1.2247 B.14 P.11 1.2303 V.70 s.i 1.2359 V.126 P.11 1.2248 B.15 P.11 1.2304 V.71 s.i 1.2360 V.127 P.11 1.2249 V.16 P.11 1.2305 V.72 s.i 1.2361 V.128 P.11 1.2250 B.17 P.11 1.2306 V.73 s.i 1.2362 V.129 P.11 1.2251 V.18 P.11 1.2307 V.74 s.i 1.2363 V.130 P.11 1.2252 V.19 P.11 1.2308 V.75 s.i 1.2364 V.131 P.11 1.2253 IN 20 P.11 1.2309 V.76 s.i 1.2365 V.132 P.11 1.2254 AT 21 P.11 1.2310 V.77 s.i 1.2366 V.133 P.11 1.2255 V.22 P.11 1.2311 V.78 s.i 1.2367 V.134 P.11 1.2256 V.23 P.11 1.2312 V.79 P.11 1.2368 V.135 P.11 1.2257 V.24 P.11 1.2313 V.80 s.i 1.2369 V.136 P.11 1.2258 V.25 P.11 1.2314 V.81 s.i 1.2370 V.137 P.11 1.2259 V.26 P.11 1.2315 V.82 s.i 1.2371 V.138 P.11 1.2260 V.27 P.11 1.2316 V.83 s.i 1.2372 V.139 P.11 1.2261 V.28 P.11 1.2317 V.84 s.i 1.2373 V.140 P.11 1.2262 V.29 P.11 1.2318 V.85 s.i 1.2374 V.141 P.11 1.2263 V.ZO P.11 1.2319 V.86 s.i 1.2375 V.142 P.11 1.2264 B.31 P.11 1.2320 V.87 s.i 1.2376 V.143 P.11 1.2265 V.32 P.11 1.2321 V.88 P.11 1.2377 V.144 P.11 1.2266 V.ZZ P.11 1.2322 V.89 s.i 1.2378 V.145 P.11 1.2267 V.34 P.11 1.2323 V.90 s.i 1.2379 V.146 P.11 1.2268 V.35 P.11 1.2324 V.91 s.i 1.2380 V.147 P.11 1.2269 V.36 P.11 1.2325 V.92 s.i 1.2381 V.148 P.11 1.2270 V.37 P.11 1.2326 V.93 s.i 1.2382 V.149 P.11 1.2271 V.38 P.11 1.2327 V.94 s.i 1.2383 V.150 P.11 1.2272 V.39 P.11 1.2328 V.95 s.i 1.2384 V.151 P.11 1.2273 B.40 P.11 1.2329 V.96 s.i 1.2385 V.152 P.11 1.2274 V.41 P.11 1.2330 V.97 s.i 1.2386 V.153 P.11 1.2275 V.42 P.11 1.2331 V.98 s.i 1.2387 V.154 P.11 1.2276 V.43 P.11 1.2332 V.99 s.i 1.2388 V.155 P.11 1.2277 V.44 P.11 1.2333 V.100 s.i 1.2389 V.156 P.11 1.2278 V.45 P.11 1.2334 V.101 s.i 1.2390 V.157 P.11 1.2279 B.46 P.11 1.2335 V.102 s.i 1.2391 V.158 SI 1.2280 V.47 P.11 1.2336 V.103 s.i 1.2392 V.159 s.i 1.2281 V.48 P.11 1.2337 V.104 s.i 1.2393 V.160 s.i 1.2282 V.49 P.11 1.2338 V.105 s.i 1.2394 V.161 s.i 1.2283 V.50 P.11 1.2339 V.106 s.i 1.2395 V.162 s.i 1.2284 V.51 P.11 1.2340 V.107 P.11 1.2396 V.163 s.i 1.2285 V.52 P.11 1.2341 V.108 s.i 1.2397 V.164 s.i 1.2286 V.53 P.11 1.2342 V.109 s.i 1.2398 V.165 s.i 1.2287 V.54 P.11 1.2343 V.110 s.i 1.2399 V.166 s.i 1.2288 V.55 P.11 1.2344 V.111 s.i 1.2400 V.167 s.i

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1.2401 V.168 P.11 1.2402 V.169 P.11 1.2403 V.170 P.11 1.2404 V.171 P.11 1.2405 V.172 P.11 1.2406 V.173 P.11 1.2407 V.174 P.11 1.2408 V.175 P.11 1.2409 V.176 P.11 1.2410 V.177 P.11 1.2411 V.178 P.11 1.2412 V.179 P.11 1.2413 V.180 P.11 1.2414 V.181 P.11 1.2415 V.182 P.11 1.2416 V.183 P.11 1.2417 V.184 P.11 1.2418 V.185 P.11 1.2419 V.186 P.11 1.2420 V.187 P.11 1.2421 V.188 P.11 1.2422 V.189 P.11 1.2423 V.190 P.11 1.2424 V.191 P.11 1.2425 V.192 P.11 1.2426 V.193 P.11 1.2427 V.194 P.11 1.2428 V.195 P.11 1.2429 V.196 P.11 1.2430 V.197 P.11 1.2431 V.198 P.11 1.2432 V.199 P.11 1.2433 V.200 P.11 1.2434 V.201 P.11 1.2435 V.202 P.11 1.2436 V.203 P.11

- 66 044989

1.2492 V.56 P.12 1.2548 V.112 P.12 1.2437 B.1 P.12 1.2493 V.57 P.12 1.2549 V.113 P.12 1.2438 B.2 P.12 1.2494 V.58. P.12 1.2550 V.114 P.12 1.2439 V.Z P.12 1.2495 V.59 P.12 1.2551 V.115 P.12 1.2440 B.4 P.12 1.2496 B.60 P.12 1.2552 V.116 P.12 1.2441 AT 5 P.12 1.2497 V.61 P.12 1.2553 V.117 P.12 1.2442 AT 6 P.12 1.2498 V.62 P.12 1.2554 V.118 P.12 1.2443 AT 7 P.12 1.2499 V.63 P.12 1.2555 V.119 P.12 1.2444 AT 8 P.12 1.2500 V.64 P.12 1.2556 V.120 P.12 1.2445 AT 9 P.12 1.2501 V.65 P.12 1.2557 V.121 P.12 1.2446 AT 10 P.12 1.2502 V.66 P.12 1.2558 V.122 P.12 1.2447 AT 11 P.12 1.2503 V.67 P.12 1.2559 V.123 P.12 1.2448 AT 12 P.12 1.2504 V.68 P.12 1.2560 V.124 P.12 1.2449 B.13 P.12 1.2505 V.69 P.12 1.2561 V.125 P.12 1.2450 B.14 P.12 1.2506 V.70 P.12 1.2562 V.126 P.12 1.2451 B.15 P.12 1.2507 V.71 P.12 1.2563 V.127 P.12 1.2452 V.16 P.12 1.2508 V.72 P.12 1.2564 V.128 P.12 1.2453 B.17 P.12 1.2509 V.73 P.12 1.2565 V.129 P.12 1.2454 V.18 P.12 1.2510 V.74 P.12 1.2566 V.130 P.12 1.2455 V.19 P.12 1.2511 V.75 P.12 1.2567 V.131 P.12 1.2456 IN 20 P.12 1.2512 V.76 P.12 1.2568 V.132 P.12 1.2457 AT 21 P.12 1.2513 V.77 P.12 1.2569 V.133 P.12 1.2458 V.22 P.12 1.2514 V.78 P.12 1.2570 V.134 P.12 1.2459 V.23 P.12 1.2515 V.79 P.12 1.2571 V.135 P.12 1.2460 V.24 P.12 1.2516 V.80 P.12 1.2572 V.136 P.12 1.2461 V.25 P.12 1.2517 V.81 P.12 1.2573 V.137 P.12 1.2462 V.26 P.12 1.2518 V.82 P.12 1.2574 V.138 P.12 1.2463 V.27 P.12 1.2519 V.83 P.12 1.2575 V.139 P.12 1.2464 V.28 P.12 1.2520 V.84 P.12 1.2576 V.140 P.12 1.2465 V.29 P.12 1.2521 V.85 P.12 1.2577 V.141 P.12 1.2466 V.ZO P.12 1.2522 V.86 P.12 1.2578 V.142 P.12 1.2467 B.31 P.12 1.2523 V.87 P.12 1.2579 V.143 P.12 1.2468 V.32 P.12 1.2524 V.88 P.12 1.2580 V.144 P.12 1.2469 V.ZZ P.12 1.2525 V.89 P.12 1.2581 V.145 P.12 1.2470 V.34 P.12 1.2526 V.90 P.12 1.2582 V.146 P.12 1.2471 V.35 P.12 1.2527 V.91 P.12 1.2583 V.147 P.12 1.2472 V.36 P.12 1.2528 V.92 P.12 1.2584 V.148 P.12 1.2473 V.37 P.12 1.2529 V.93 P.12 1.2585 V.149 P.12 1.2474 V.38 P.12 1.2530 V.94 P.12 1.2586 V.150 P.12 1.2475 V.39 P.12 1.2531 V.95 P.12 1.2587 V.151 P.12 1.2476 B.40 P.12 1.2532 V.96 P.12 1.2588 V.152 P.12 1.2477 V.41 P.12 1.2533 V.97 P.12 1.2589 V.153 P.12 1.2478 V.42 P.12 1.2534 V.98 P.12 1.2590 V.154 P.12 1.2479 V.43 P.12 1.2535 V.99 P.12 1.2591 V.155 P.12 1.2480 V.44 P.12 1.2536 V.100 P.12 1.2592 V.156 P.12 1.2481 V.45 P.12 1.2537 V.101 P.12 1.2593 V.157 P.12 1.2482 V.46 P.12 1.2538 V.102 P.12 1.2594 V.158 P.12 1.2483 V.47 P.12 1.2539 V.103 P.12 1.2595 V.159 P.12 1.2484 V.48 P.12 1.2540 V.104 P.12 1.2596 V.160 P.12 1.2485 V.49 P.12 1.2541 V.105 P.12 1.2597 V.161 P.12 1.2486 V.50 P.12 1.2542 V.106 P.12 1.2598 V.162 P.12 1.2487 V.51 P.12 1.2543 V.107 P.12 1.2599 V.163 P.12 1.2488 V.52 P.12 1.2544 V.108 P.12 1.2600 V.164 P.12 1.2489 V.53 P.12 1.2545 V.109 P.12 1.2601 V.165 P.12 1.2490 V.54 P.12 1.2546 V.PO P.12 1.2602 V.166 P.12 1.2491 V.55 P.12 1.2547 V.111 P.12 1.2603 V.167 P.12

- 67 044989

1.2604 V.168 P.12 1.2605 V.169 P.12 1.2606 V.170 P.12 1.2607 V.171 P.12 1.2608 V.172 P.12 1.2609 V.173 P.12 1.2610 V.174 P.12 1.2611 V.175 P.12 1.2612 V.176 P.12 1.2613 V.177 P.12 1.2614 V.178 P.12 1.2615 V.179 P.12 1.2616 V.180 P.12 1.2617 V.181 P.12 1.2618 V.182 P.12 1.2619 V.183 P.12 1.2620 V.184 P.12 1.2621 V.185 P.12 1.2622 V.186 P.12 1.2623 V.187 P.12 1.2624 V.188 P.12 1.2625 V.189 P.12 1.2626 V.190 P.12 1.2627 V.191 P.12 1.2628 V.192 P.12 1.2629 V.193 P.12 1.2630 V.194 P.12 1.2631 V.195 P.12 1.2632 V.196 P.12 1.2633 V.197 P.12 1.2634 V.198 P.12 1.2635 V.199 P.12 1.2636 V.200 P.12 1.2637 V.201 P.12 1.2638 V.202 P.12 1.2639 V.203 P.12

- 68 044989

1.2695 V.56 P.13 1.2751 V.112 P.13 1.2640 B.l P.13 1.2696 V.57 P.13 1.2752 V.IZ P.13 1.2641 B.2 P.13 1.2697 V.58. P.13 1.2753 V.114 P.13 1.2642 V.Z P.13 1.2698 V.59 P.13 1.2754 V.115 P.13 1.2643 B.4 P.13 1.2699 B.60 P.13 1.2755 V.116 P.13 1.2644 AT 5 P.13 1.2700 V.61 P.13 1.2756 V.117 P.13 1.2645 AT 6 P.13 1.2701 V.62 P.13 1.2757 V.118 P.13 1.2646 AT 7 P.13 1.2702 V.63 P.13 1.2758 V.119 P.13 1.2647 AT 8 P.13 1.2703 V.64 P.13 1.2759 V.120 P.13 1.2648 AT 9 P.13 1.2704 V.65 P.13 1.2760 V.121 P.13 1.2649 AT 10 P.13 1.2705 V.66 P.13 1.2761 V.122 P.13 1.2650 IN AND P.13 1.2706 V.67 P.13 1.2762 V.123 P.13 1.2651 AT 12 P.13 1.2707 V.68 P.13 1.2763 V.124 P.13 1.2652 B.13 P.13 1.2708 V.69 P.13 1.2764 V.125 P.13 1.2653 B.14 P.13 1.2709 V.70 P.13 1.2765 V.126 P.13 1.2654 B.15 P.13 1.2710 V.71 P.13 1.2766 V.127 P.13 1.2655 V.16 P.13 1.2711 V.72 P.13 1.2767 V.128 P.13 1.2656 B.17 P.13 1.2712 V.73 P.13 1.2768 V.129 P.13 1.2657 V.18 P.13 1.2713 V.74 P.13 1.2769 V.130 P.13 1.2658 V.19 P.13 1.2714 V.75 P.13 1.2770 V.131 P.13 1.2659 IN 20 P.13 1.2715 V.76 P.13 1.2771 V.132 P.13 1.2660 AT 21 P.13 1.2716 V.77 P.13 1.2772 V.133 P.13 1.2661 V.22 P.13 1.2717 V.78 P.13 1.2773 V.134 P.13 1.2662 V.23 P.13 1.2718 V.79 P.13 1.2774 V.135 P.13 1.2663 V.24 P.13 1.2719 V.80 P.13 1.2775 V.136 P.13 1.2664 V.25 P.13 1.2720 V.81 P.13 1.2776 V.137 P.13 1.2665 V.26 P.13 1.2721 V.82 P.13 1.2777 V.138 P.13 1.2666 V.27 P.13 1.2722 V.83 P.13 1.2778 V.139 P.13 1.2667 V.28 P.13 1.2723 V.84 P.13 1.2779 V.140 P.13 1.2668 V.29 P.13 1.2724 V.85 P.13 1.2780 V.141 P.13 1.2669 V.ZO P.13 1.2725 V.86 P.13 1.2781 V.142 P.13 1.2670 B.31 P.13 1.2726 V.87 P.13 1.2782 V.143 P.13 1.2671 V.32 P.13 1.2727 V.88 P.13 1.2783 V.144 P.13 1.2672 V.ZZ P.13 1.2728 V.89 P.13 1.2784 V.145 P.13 1.2673 V.34 P.13 1.2729 V.90 P.13 1.2785 V.146 P.13 1.2674 V.35 P.13 1.2730 V.91 P.13 1.2786 V.147 P.13 1.2675 V.36 P.13 1.2731 V.92 P.13 1.2787 V.148 P.13 1.2676 V.37 P.13 1.2732 V.93 P.13 1.2788 V.149 P.13 1.2677 V.38 P.13 1.2733 V.94 P.13 1.2789 V.150 P.13 1.2678 V.39 P.13 1.2734 V.95 P.13 1.2790 V.151 P.13 1.2679 B.40 P.13 1.2735 V.96 P.13 1.2791 V.152 P.13 1.2680 V.41 P.13 1.2736 V.97 P.13 1.2792 V.153 P.13 1.2681 V.42 P.13 1.2737 V.98 P.13 1.2793 V.154 P.13 1.2682 V.43 P.13 1.2738 V.99 P.13 1.2794 V.155 P.13 1.2683 V.44 P.13 1.2739 V.100 P.13 1.2795 V.156 P.13 1.2684 V.45 P.13 1.2740 V.101 P.13 1.2796 V.157 P.13 1.2685 V.46 P.13 1.2741 V.102 P.13 1.2797 V.158 P.13 1.2686 V.47 P.13 1.2742 V.103 P.13 1.2798 V.159 P.13 1.2687 V.48 P.13 1.2743 V.104 P.13 1.2799 V.160 P.13 1.2688 V.49 P.13 1.2744 V.105 P.13 1.2800 V.161 P.13 1.2689 V.50 P.13 1.2745 V.106 P.13 1.2801 V.162 P.13 1.2690 V.51 P.13 1.2746 V.107 P.13 1.2802 V.163 P.13 1.2691 V.52 P.13 1.2747 V.108 P.13 1.2803 V.164 P.13 1.2692 V.53 P.13 1.2748 V.109 P.13 1.2804 V.165 P.13 1.2693 V.54 P.13 1.2749 V.110 P.13 1.2805 V.166 P.13 1.2694 V.55 P.13 1.2750 V.111 P.13 1.2806 V.167 P.13

- 69 044989

1.2807 V.168 P.13 1.2808 V.169 P.13 1.2809 V.170 P.13 1.2810 V.171 P.13 1.2811 V.172 P.13 1.2812 V.173 P.13 1.2813 V.174 P.13 1.2814 V.175 P.13 1.2815 V.176 P.13 1.2816 V.177 P.13 1.2817 V.178 P.13 1.2818 V.179 P.13 1.2819 V.180 P.13 1.2820 V.181 P.13 1.2821 V.182 P.13 1.2822 V.183 P.13 1.2823 V.184 P.13 1.2824 V.185 P.13 1.2825 V.186 P.13 1.2826 V.187 P.13 1.2827 V.188 P.13 1.2828 V.189 P.13 1.2829 V.190 P.13 1.2830 V.191 P.13 1.2831 V.192 P.13 1.2832 V.193 P.13 1.2833 V.194 P.13 1.2834 V.195 P.13 1.2835 V.196 P.13 1.2836 V.197 P.13 1.2837 V.198 P.13 1.2838 V.199 P.13 1.2839 V.200 P.13 1.2840 V.201 P.13 1.2841 V.202 P.13 1.2842 V.203 P.13

- 70 044989

1.2843 B.l P.14 1.2844 B.2 P.14 1.2845 V.Z P.14 1.2846 B.4 P.14 1.2847 AT 5 P.14 1.2848 AT 6 P.14 1.2849 AT 7 P.14 1.2850 AT 8 P.14 1.2851 AT 9 P.14 1.2852 AT 10 P.14 1.2853 in and P.14 1.2854 AT 12 P.14 1.2855 B.13 P.14 1.2856 B.14 P.14 1.2857 B.15 P.14 1.2858 V.16 P.14 1.2859 B.17 P.14 1.2860 V.18 P.14 1.2861 V.19 P.14 1.2862 IN 20 P.14 1.2863 AT 21 P.14 1.2864 V.22 P.14 1.2865 V.23 P.14 1.2866 V.24 P.14 1.2867 V.25 P.14 1.2868 V.26 P.14 1.2869 V.27 P.14 1.2870 V.28 P.14 1.2871 V.29 P.14 1.2872 V.ZO P.14 1.2873 B.31 P.14 1.2874 V.32 P.14 1.2875 V.ZZ P.14 1.2876 V.34 P.14 1.2877 V.35 P.14 1.2878 V.36 P.14 1.2879 V.37 P.14 1.2880 V.38 P.14 1.2881 V.39 P.14 1.2882 B.40 P.14 1.2883 V.41 P.14 1.2884 V.42 P.14 1.2885 V.43 P.14 1.2886 V.44 P.14 1.2887 At 45 P.14 1.2888 V.46 P.14 1.2889 V.47 P.14 1.2890 V.48 P.14 1.2891 V.49 P.14 1.2892 V.50 P.14 1.2893 V.51 P.14 1.2894 V.52 P.14 1.2895 V.53 P.14 1.2896 V.54 P.14

1.2897 V.55 P.14 1.2898 V.56 P.14 1.2899 V.57 P.14 1.2900 V.58. P.14 1.2901 V.59 P.14 1.2902 B.60 P.14 1.2903 V.61 P.14 1.2904 V.62 P.14 1.2905 V.63 P.14 1.2906 V.64 P.14 1.2907 V.65 P.14 1.2908 V.66 P.14 1.2909 V.67 P.14 1.2910 V.68 P.14 1.2911 V.69 P.14 1.2912 V.70 P.14 1.2913 V.71 P.14 1.2914 V.72 P.14 1.2915 V.73 P.14 1.2916 V.74 P.14 1.2917 V.75 P.14 1.2918 V.76 P.14 1.2919 V.77 P.14 1.2920 V.78 P.14 1.2921 V.79 P.14 1.2922 V.80 P.14 1.2923 V.81 P.14 1.2924 V.82 P.14 1.2925 V.83 P.14 1.2926 V.84 P.14 1.2927 V.85 P.14 1.2928 V.86 P.14 1.2929 V.87 P.14 1.2930 V.88 P.14 1.2931 V.89 P.14 1.2932 V.90 P.14 1.2933 V.91 P.14 1.2934 V.92 P.14 1.2935 V.93 P.14 1.2936 V.94 P.14 1.2937 V.95 P.14 1.2938 V.96 P.14 1.2939 V.97 P.14 1.2940 V.98 P.14 1.2941 V.99 P.14 1.2942 V.100 P.14 1.2943 V.101 P.14 1.2944 V. 102 P.14 1.2945 V.103 P.14 1.2946 V. 104 P.14 1.2947 V.105 P.14 1.2948 V.106 P.14 1.2949 V.107 P.14 1.2950 V.108 P.14 1.2951 V.109 P.14 1.2952 V.110 P.14

1.2953 V.111 P.14 1.2954 V.112 P.14 1.2955 V.IZ P.14 1.2956 V.114 P.14 1.2957 V.115 P.14 1.2958 V.116 P.14 1.2959 V.117 P.14 1.2960 V.118 P.14 1.2961 V.119 P.14 1.2962 V.120 P.14 1.2963 V.121 P.14 1.2964 V.122 P.14 1.2965 V.123 P.14 1.2966 V.124 P.14 1.2967 V.125 P.14 1.2968 V.126 P.14 1.2969 V.127 P.14 1.2970 V.128 P.14 1.2971 V.129 P.14 1.2972 V.130 P.14 1.2973 V.131 P.14 1.2974 V.132 P.14 1.2975 V.133 P.14 1.2976 V.134 P.14 1.2977 V.135 P.14 1.2978 V.136 P.14 1.2979 V.137 P.14 1.2980 V.138 P.14 1.2981 V.139 P.14 1.2982 V.140 P.14 1.2983 V.141 P.14 1.2984 V.142 P.14 1.2985 V.143 P.14 1.2986 V.144 P.14 1.2987 V.145 P.14 1.2988 V.146 P.14 1.2989 V.147 P.14 1.2990 V.148 P.14 1.2991 V.149 P.14 1.2992 V.150 P.14 1.2993 V.151 P.14 1.2994 V.152 P.14 1.2995 V.153 P.14 1.2996 V.154 P.14 1.2997 V.155 P.14 1.2998 V.156 P.14 1.2999 V.157 P.14 1.3000 V.158 P.14 1.3001 V.159 P.14 1.3002 V.160 P.14 1.3003 V.161 P.14 1.3004 V.162 P.14 1.3005 V.163 P.14 1.3006 V.164 P.14 1.3007 V.165 P.14 1.3008 V.166 P.14

- 71 044989

1.3009 V.167 P.14 1.3010 V.168 P.14 1.3011 V.169 P.14 1.3012 V.170 P.14 1.3013 V.171 P.14 1.3014 V.172 P.14 1.3015 V.173 P.14 1.3016 V.174 P.14 1.3017 V.175 P.14 1.3018 V.176 P.14 1.3019 V.177 P.14 1.3020 V.178 P.14 1.3021 V.179 P.14 1.3022 V.180 P.14 1.3023 V.181 P.14 1.3024 V.182 P.14 1.3025 V.183 P.14 1.3026 V.184 P.14 1.3027 V.185 P.14 1.3028 V.186 P.14 1.3029 V.187 P.14 1.3030 V.188 P.14 1.3031 V.189 P.14 1.3032 V.190 P.14 1.3033 V.191 P.14 1.3034 V.192 P.14 1.3035 V.193 P.14 1.3036 V.194 P.14 1.3037 V.195 P.14 1.3038 V.196 P.14 1.3039 V.197 P.14 1.3040 V.198 P.14 1.3041 V.199 P.14 1.3042 V.200 P.14 1.3043 V.201 P.14 1.3044 V.202 P.14 1.3045 V.203 P.14

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1.3100 V.55 P.15 1.3156 V.111 P.15 1.3101 V.56 P.15 1.3157 V.112 P.15 1.3046 B.l P.15 1.3102 V.57 P.15 1.3158 V.IZ P.15 1.3047 B.2 P.15 1.3103 V.58. P.15 1.3159 V.114 P.15 1.3048 V.Z P.15 1.3104 V.59 P.15 1.3160 V.115 P.15 1.3049 B.4 P.15 1.3105 B.60 P.15 1.3161 V.116 P.15 1.3050 AT 5 P.15 1.3106 V.61 P.15 1.3162 V.117 P.15 1.3051 AT 6 P.15 1.3107 V.62 P.15 1.3163 V.118 P.15 1.3052 AT 7 P.15 1.3108 V.63 P.15 1.3164 V.119 P.15 1.3053 AT 8 P.15 1.3109 V.64 P.15 1.3165 V.120 P.15 1.3054 AT 9 P.15 1.3110 V.65 P.15 1.3166 V.121 P.15 1.3055 AT 10 P.15 1.3111 V.66 P.15 1.3167 V.122 P.15 1.3056 in and P.15 1.3112 V.67 P.15 1.3168 V.123 P.15 1.3057 AT 12 P.15 1.3113 V.68 P.15 1.3169 V.124 P.15 1.3058 B.13 P.15 1.3114 V.69 P.15 1.3170 V.125 P.15 1.3059 B.14 P.15 1.3115 V.70 P.15 1.3171 V.126 P.15 1.3060 B.15 P.15 1.3116 V.71 P.15 1.3172 V.127 P.15 1.3061 V.16 P.15 1.3117 V.72 P.15 1.3173 V.128 P.15 1.3062 B.17 P.15 1.3118 V.73 P.15 1.3174 V.129 P.15 1.3063 V.18 P.15 1.3119 V.74 P.15 1.3175 V.130 P.15 1.3064 V.19 P.15 1.3120 V.75 P.15 1.3176 V.131 P.15 1.3065 IN 20 P.15 1.3121 V.76 P.15 1.3177 V.132 P.15 1.3066 AT 21 P.15 1.3122 V.77 P.15 1.3178 V.133 P.15 1.3067 V.22 P.15 1.3123 V.78 P.15 1.3179 V.134 P.15 1.3068 V.23 P.15 1.3124 V.79 P.15 1.3180 V.135 P.15 1.3069 V.24 P.15 1.3125 V.80 P.15 1.3181 V.136 P.15 1.3070 V.25 P.15 1.3126 V.81 P.15 1.3182 V.137 P.15 1.3071 V.26 P.15 1.3127 V.82 P.15 1.3183 V.138 P.15 1.3072 V.27 P.15 1.3128 V.83 P.15 1.3184 V.139 P.15 1.3073 V.28 P.15 1.3129 V.84 P.15 1.3185 V.140 P.15 1.3074 V.29 P.15 1.3130 V.85 P.15 1.3186 V.141 P.15 1.3075 V.ZO P.15 1.3131 V.86 P.15 1.3187 V.142 P.15 1.3076 B.31 P.15 1.3132 V.87 P.15 1.3188 V.143 P.15 1.3077 V.32 P.15 1.3133 V.88 P.15 1.3189 V.144 P.15 1.3078 V.ZZ P.15 1.3134 V.89 P.15 1.3190 V.145 P.15 1.3079 V.34 P.15 1.3135 V.90 P.15 1.3191 V.146 P.15 1.3080 V.35 P.15 1.3136 V.91 P.15 1.3192 V.147 P.15 1.3081 V.36 P.15 1.3137 V.92 P.15 1.3193 V.148 P.15 1.3082 V.37 P.15 1.3138 V.93 P.15 1.3194 V.149 P.15 1.3083 V.38 P.15 1.3139 V.94 P.15 1.3195 V.150 P.15 1.3084 V.39 P.15 1.3140 V.95 P.15 1.3196 V.151 P.15 1.3085 B.40 P.15 1.3141 V.96 P.15 1.3197 V.152 P.15 1.3086 V.41 P.15 1.3142 V.97 P.15 1.3198 V.153 P.15 1.3087 V.42 P.15 1.3143 V.98 P.15 1.3199 V.154 P.15 1.3088 V.43 P.15 1.3144 V.99 P.15 1.3200 V.155 P.15 1.3089 V.44 P.15 1.3145 V.100 P.15 1.3201 V.156 P.15 1.3090 V.45 P.15 1.3146 V.101 P.15 1.3202 V.157 P.15 1.3091 V.46 P.15 1.3147 V. 102 P.15 1.3203 V.158 P.15 1.3092 V.47 P.15 1.3148 V.103 P.15 1.3204 V.159 P.15 1.3093 V.48 P.15 1.3149 V. 104 P.15 1.3205 V.160 P.15 1.3094 V.49 P.15 1.3150 V.105 P.15 1.3206 V.161 P.15 1.3095 V.50 P.15 1.3151 V.106 P.15 1.3207 V.162 P.15 1.3096 V.51 P.15 1.3152 V.107 P.15 1.3208 V.163 P.15 1.3097 V.52 P.15 1.3153 V.108 P.15 1.3209 V.164 P.15 1.3098 V.53 P.15 1.3154 V.109 P.15 1.3210 V.165 P.15 1.3099 V.54 P.15 1.3155 V.110 P.15 1.3211 V.166 P.15

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1.3212 V.167 P.15 1.3213 V.168 P.15 1.3214 V.169 P.15 1.3215 V.170 P.15 1.3216 V.171 P.15 1.3217 V.172 P.15 1.3218 V.173 P.15 1.3219 V.174 P.15 1.3220 V.175 P.15 1.3221 V.176 P.15 1.3222 V.177 P.15 1.3223 V.178 P.15 1.3224 V.179 P.15 1.3225 V.180 P.15 1.3226 V.181 P.15 1.3227 V.182 P.15 1.3228 V.183 P.15 1.3229 V.184 P.15 1.3230 V.185 P.15 1.3231 V.186 P.15 1.3232 V.187 P.15 1.3233 V.188 P.15 1.3234 V.189 P.15 1.3235 V.190 P.15 1.3236 V.191 P.15 1.3237 V.192 P.15 1.3238 V.193 P.15 1.3239 V.194 P.15 1.3240 V.195 P.15 1.3241 V.196 P.15 1.3242 V.197 P.15 1.3243 V.198 P.15 1.3244 V.199 P.15 1.3245 V.200 P.15 1.3246 V.201 P.15 1.3247 V.202 P.15 1.3248 V.203 P.15

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1.3303 V.55 P.16 1.3359 V.111 P.16 1.3304 V.56 P.16 1.3360 V.112 P.16 1.3249 B.l P.16 1.3305 V.57 P.16 1.3361 V.IZ P.16 1.3250 B.2 P.16 1.3306 V.58. P.16 1.3362 V.114 P.16 1.3251 V.Z P.16 1.3307 V.59 P.16 1.3363 V.115 P.16 1.3252 B.4 P.16 1.3308 B.60 P.16 1.3364 V.116 P.16 1.3253 AT 5 P.16 1.3309 V.61 P.16 1.3365 V.117 P.16 1.3254 AT 6 P.16 1.3310 V.62 P.16 1.3366 V.118 P.16 1.3255 AT 7 P.16 1.3311 V.63 P.16 1.3367 V.119 P.16 1.3256 AT 8 P.16 1.3312 V.64 P.16 1.3368 V.120 P.16 1.3257 AT 9 P.16 1.3313 V.65 P.16 1.3369 V.121 P.16 1.3258 AT 10 P.16 1.3314 V.66 P.16 1.3370 V.122 P.16 1.3259 in and P.16 1.3315 V.67 P.16 1.3371 V.123 P.16 1.3260 AT 12 P.16 1.3316 V.68 P.16 1.3372 V.124 P.16 1.3261 B.13 P.16 1.3317 V.69 P.16 1.3373 V.125 P.16 1.3262 B.14 P.16 1.3318 V.70 P.16 1.3374 V.126 P.16 1.3263 B.15 P.16 1.3319 V.71 P.16 1.3375 V.127 P.16 1.3264 V.16 P.16 1.3320 V.72 P.16 1.3376 V.128 P.16 1.3265 B.17 P.16 1.3321 V.73 P.16 1.3377 V.129 P.16 1.3266 V.18 P.16 1.3322 V.74 P.16 1.3378 V.130 P.16 1.3267 V.19 P.16 1.3323 V.75 P.16 1.3379 V.131 P.16 1.3268 IN 20 P.16 1.3324 V.76 P.16 1.3380 V.132 P.16 1.3269 AT 21 P.16 1.3325 V.77 P.16 1.3381 V.133 P.16 1.3270 V.22 P.16 1.3326 V.78 P.16 1.3382 V.134 P.16 1.3271 V.23 P.16 1.3327 V.79 P.16 1.3383 V.135 P.16 1.3272 V.24 P.16 1.3328 V.80 P.16 1.3384 V.136 P.16 1.3273 V.25 P.16 1.3329 V.81 P.16 1.3385 V.137 P.16 1.3274 V.26 P.16 1.3330 V.82 P.16 1.3386 V.138 P.16 1.3275 V.27 P.16 1.3331 V.83 P.16 1.3387 V.139 P.16 1.3276 V.28 P.16 1.3332 V.84 P.16 1.3388 V.140 P.16 1.3277 V.29 P.16 1.3333 V.85 P.16 1.3389 V.141 P.16 1.3278 V.ZO P.16 1.3334 V.86 P.16 1.3390 V.142 P.16 1.3279 B.31 P.16 1.3335 V.87 P.16 1.3391 V.143 P.16 1.3280 V.32 P.16 1.3336 V.88 P.16 1.3392 V.144 P.16 1.3281 V.ZZ P.16 1.3337 V.89 P.16 1.3393 V.145 P.16 1.3282 V.34 P.16 1.3338 V.90 P.16 1.3394 V.146 P.16 1.3283 V.35 P.16 1.3339 V.91 P.16 1.3395 V.147 P.16 1.3284 V.36 P.16 1.3340 V.92 P.16 1.3396 V.148 P.16 1.3285 V.37 P.16 1.3341 V.93 P.16 1.3397 V.149 P.16 1.3286 V.38 P.16 1.3342 V.94 P.16 1.3398 V.150 P.16 1.3287 V.39 P.16 1.3343 V.95 P.16 1.3399 V.151 P.16 1.3288 B.40 P.16 1.3344 V.96 P.16 1.3400 V.152 P.16 1.3289 V.41 P.16 1.3345 V.97 P.16 1.3401 V.153 P.16 1.3290 V.42 P.16 1.3346 V.98 P.16 1.3402 V.154 P.16 1.3291 V.43 P.16 1.3347 V.99 P.16 1.3403 V.155 P.16 1.3292 V.44 P.16 1.3348 V.100 P.16 1.3404 V.156 P.16 1.3293 V.45 P.16 1.3349 V.101 P.16 1.3405 V.157 P.16 1.3294 V.46 P.16 1.3350 V.102 P.16 1.3406 V.158 P.16 1.3295 V.47 P.16 1.3351 V.103 P.16 1.3407 V.159 P.16 1.3296 V.48 P.16 1.3352 V.104 P.16 1.3408 V.160 P.16 1.3297 V.49 P.16 1.3353 V.105 P.16 1.3409 V.161 P.16 1.3298 V.50 P.16 1.3354 V.106 P.16 1.3410 V.162 P.16 1.3299 V.51 P.16 1.3355 V.107 P.16 1.3411 V.163 P.16 1.3300 V.52 P.16 1.3356 V.108 P.16 1.3412 V.164 P.16 1.3301 V.53 P.16 1.3357 V.109 P.16 1.3413 V.165 P.16 1.3302 V.54 P.16 1.3358 V.110 P.16 1.3414 V.166 P.16

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1.3415 V.167 P.16 1.3416 V.168 P.16 1.3417 V.169 P.16 1.3418 V.170 P.16 1.3419 V.171 P.16 1.3420 V.172 P.16 1.3421 V.173 P.16 1.3422 V.174 P.16 1.3423 V.175 P.16 1.3424 V.176 P.16 1.3425 V.177 P.16 1.3426 V.178 P.16 1.3427 V.179 P.16 1.3428 V.180 P.16 1.3429 V.181 P.16 1.3430 V.182 P.16 1.3431 V.183 P.16 1.3432 V.184 P.16 1.3433 V.185 P.16 1.3434 V.186 P.16 1.3435 V.187 P.16 1.3436 V.188 P.16 1.3437 V.189 P.16 1.3438 V.190 P.16 1.3439 V.191 P.16 1.3440 V.192 P.16 1.3441 V.193 P.16 1.3442 V.194 P.16 1.3443 V.195 P.16 1.3444 V.196 P.16 1.3445 V.197 P.16 1.3446 V.198 P.16 1.3447 V.199 P.16 1.3448 V.200 P.16 1.3449 V.201 P.16 1.3450 V.202 P.16 1.3451 V.203 P.16

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1.3506 V.55 P.17 1.3562 V.111 P.17 1.3507 V.56 P.17 1.3563 V.112 P.17 1.3452 B.l P.17 1.3508 V.57 P.17 1.3564 V.IZ P.17 1.3453 B.2 P.17 1.3509 V.58. P.17 1.3565 V.114 P.17 1.3454 v.z. P.17 1.3510 V.59 P.17 1.3566 V.115 P.17 1.3455 B.4 P.17 1.3511 B.60 P.17 1.3567 V.116 P.17 1.3456 AT 5 P.17 1.3512 V.61 P.17 1.3568 V.117 P.17 1.3457 B.6 P.17 1.3513 V.62 P.17 1.3569 V.118 P.17 1.3458 B.7 P.17 1.3514 V.63 P.17 1.3570 V.119 P.17 1.3459 B.8 P.17 1.3515 V.64 P.17 1.3571 V.120 P.17 1.3460 AT 9 P.17 1.3516 V.65 P.17 1.3572 V.121 P.17 1.3461 AT 10 P.17 1.3517 V.66 P.17 1.3573 V.122 P.17 1.3462 in and P.17 1.3518 V.67 P.17 1.3574 V.123 P.17 1.3463 AT 12 P.17 1.3519 V.68 P.17 1.3575 V.124 P.17 1.3464 B.13 P.17 1.3520 V.69 P.17 1.3576 V.125 P.17 1.3465 B.14 P.17 1.3521 V.70 P.17 1.3577 V.126 P.17 1.3466 B.15 P.17 1.3522 V.71 P.17 1.3578 V.127 P.17 1.3467 V.16 P.17 1.3523 V.72 P.17 1.3579 V.128 P.17 1.3468 B.17 P.17 1.3524 V.73 P.17 1.3580 V.129 P.17 1.3469 V.18 P.17 1.3525 V.74 P.17 1.3581 V.130 P.17 1.3470 V.19 P.17 1.3526 V.75 P.17 1.3582 V.131 P.17 1.3471 B.20 P.17 1.3527 V.76 P.17 1.3583 V.132 P.17 1.3472 B.21 P.17 1.3528 V.77 P.17 1.3584 V.133 P.17 1.3473 V.22 P.17 1.3529 V.78 P.17 1.3585 V.134 P.17 1.3474 V.23 P.17 1.3530 V.79 P.17 1.3586 V.135 P.17 1.3475 V.24 P.17 1.3531 V.80 P.17 1.3587 V.136 P.17 1.3476 V.25 P.17 1.3532 V.81 P.17 1.3588 V.137 P.17 1.3477 V.26 P.17 1.3533 V.82 P.17 1.3589 V.138 P.17 1.3478 V.27 P.17 1.3534 V.83 P.17 1.3590 V.139 P.17 1.3479 V.28 P.17 1.3535 V.84 P.17 1.3591 V.140 P.17 1.3480 V.29 P.17 1.3536 V.85 P.17 1.3592 V.141 P.17 1.3481 B.30 P.17 1.3537 V.86 P.17 1.3593 V.142 P.17 1.3482 B.31 P.17 1.3538 V.87 P.17 1.3594 V.143 P.17 1.3483 V.32 P.17 1.3539 V.88 P.17 1.3595 V.144 P.17 1.3484 V.ZZ P.17 1.3540 V.89 P.17 1.3596 V.145 P.17 1.3485 V.34 P.17 1.3541 V.90 P.17 1.3597 V.146 P.17 1.3486 V.35 P.17 1.3542 V.91 P.17 1.3598 V.147 P.17 1.3487 V.36 P.17 1.3543 V.92 P.17 1.3599 V.148 P.17 1.3488 V.37 P.17 1.3544 V.93 P.17 1.3600 V.149 P.17 1.3489 V.38 P.17 1.3545 V.94 P.17 1.3601 V.150 P.17 1.3490 V.39 P.17 1.3546 V.95 P.17 1.3602 V.151 P.17 1.3491 B.40 P.17 1.3547 V.96 P.17 1.3603 V.152 P.17 1.3492 V.41 P.17 1.3548 V.97 P.17 1.3604 V.153 P.17 1.3493 V.42 P.17 1.3549 V.98 P.17 1.3605 V.154 P.17 1.3494 V.43 P.17 1.3550 V.99 P.17 1.3606 V.155 P.17 1.3495 V.44 P.17 1.3551 V.100 P.17 1.3607 V.156 P.17 1.3496 V.45 P.17 1.3552 V.101 P.17 1.3608 V.157 P.17 1.3497 V.46 P.17 1.3553 V. 102 P.17 1.3609 V.158 P.17 1.3498 V.47 P.17 1.3554 V.103 P.17 1.3610 V.159 P.17 1.3499 V.48 P.17 1.3555 V. 104 P.17 1.3611 V.160 P.17 1.3500 V.49 P.17 1.3556 V.105 P.17 1.3612 V.161 P.17 1.3501 V.50 P.17 1.3557 V.106 P.17 1.3613 V.162 P.17 1.3502 V.51 P.17 1.3558 V.107 P.17 1.3614 V.163 P.17 1.3503 V.52 P.17 1.3559 V.108 P.17 1.3615 V.164 P.17 1.3504 V.53 P.17 1.3560 V.109 P.17 1.3616 V.165 P.17 1.3505 V.54 P.17 1.3561 V.110 P.17 1.3617 V.166 P.17

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1.3655 — C.1 1.3656 — C.2 1.3657 — s.z 1.3658 — C.4 1.3659 — C.5 1.3660 — C.6

1.3618 V.167 P.17 1.3619 V.168 P.17 1.3620 V.169 P.17 1.3621 V.170 P.17 1.3622 V.171 P.17 1.3623 V.172 P.17 1.3624 V.173 P.17 1.3625 V.174 P.17 1.3626 V.175 P.17 1.3627 V.176 P.17 1.3628 V.177 P.17 1.3629 V.178 P.17 1.3630 V.179 P.17 1.3631 V.180 P.17 1.3632 V.181 P.17 1.3633 V.182 P.17 1.3634 V.183 P.17 1.3635 V.184 P.17 1.3636 V.185 P.17 1.3637 V.186 P.17 1.3638 V.187 P.17 1.3639 V.188 P.17 1.3640 V.189 P.17 1.3641 V.190 P.17 1.3642 V.191 P.17 1.3643 V.192 P.17 1.3644 V.193 P.17 1.3645 V.194 P.17 1.3646 V.195 P.17 1.3647 V.196 P.17 1.3648 V.197 P.17 1.3649 V.198 P.17 1.3650 V.199 P.17 1.3651 V.200 P.17 1.3652 V.201 P.17 1.3653 V.202 P.17 1.3654 V.203 P.17 1.3661 — P.7 1.3662 — P.8 1.3663 — P.9 1.3664 — P.10 1.3665 — S.I 1.3666 — P.12 1.3667 — P.13

1.3668 — P.14 1.3669 — P.15 1.3670 — P.16 1.3671 — P.17

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

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

The agrochemical composition contains a pesticide effective amount of a diaminotriazine compound of formula (I). The term effective amount means an amount of the composition or compounds I that 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 amount may vary over a wide range and depends on various factors such as the plants being controlled, the cultivated plant or material being treated, climatic conditions and the particular diaminotriazine compound of formula (I) used.

The diaminotriazine compound of formula (I), its N-oxides or salts can be converted into conventional types of agrochemical compositions, for example, solutions, emulsions, suspensions, dusts, powders, pastes, granules, extrudates, capsules and mixtures thereof. Examples of types of agrochemical compositions are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, lozenges, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), extrudates (e.g. BR, TB, DT), granules (e.g. WG, SG, GR,

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FG, GG, MG), insecticidal products (eg LN), also gel formulations for treating plant propagation material such as seeds (eg GF). These and other 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.

Agrochemical compositions are prepared in a known manner, such as described by 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 auxiliary agents are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration aids, protective colloids, binders, thickeners, humectants, repellents, attractants, stimulants feeding agents, compatibilizers, bactericides, antifreezes, defoamers, dyes, tackifying agents and binders.

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

Suitable solid carriers or fillers are minerals, 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, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, such as cereal flour, cinchona flour, wood flour, nut shell flour and mixtures thereof.

Suitable surfactants include surfactants such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes and mixtures thereof. Such surfactants may be used as an emulsifier, dispersant, solubilizer, wetting agent, penetration aid, protective colloid, or adjuvant. Examples of surfactants are given in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. and North American Ed.).

Suitable anionic surfactants are alkaline, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and fat sulfonates, ethoxylated alkyl phenols sulfonates, alkoxylated aryl phenols sulfonates, condensed naphthalene sulfonates, dodecyl and tridecyl benzene sulfonates, naphthalene and alkyl naphthalene sulfonates, sulfonates osuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and fats, ethoxylated alkylphenols, alcohols, ethoxylated alcohols or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants include 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. Ethylene oxide and/or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are esters, glycerol esters or monoglycerides of fatty acids. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose-glucose esters or alkyl polyglycosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinyl alcohol 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 A-B-A block polymers containing blocks of polyethylene oxide and polypropylene oxide, or type A-B-C containing alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid combination polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds that have negligible or even no pesticidal activity and that improve the biological effectiveness of Compound I on the target. Examples are surfactants, mineral or vegetable oils and other auxiliary agents. Further examples are given in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners include polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkyl isothiazolinones and benzisothiazolinones.

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

Suitable defoamers include silicones, long-chain alcohols and fatty acid salts.

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

Suitable tackifiers or binders include polyvinylpyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes and cellulose ethers. Examples of types of agrochemical compositions and their compositions are:

i) Water-soluble concentrates (SL, LS).

10-60% by weight of the diaminotriazine compound of formula (I) according to the invention and 5-15% by weight of a wetting agent (eg alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (eg alcohols) to 100% by weight. The active substance dissolves when diluted with water.

ii) Dispersible concentrates (DC).

5-25 wt.% diaminotriazine compound of formula (I) according to the invention and 1-10 wt.% dispersant (eg polyvinylpyrrolidone) are dissolved in an organic solvent (eg cyclohexanone) to 100 wt.%. Dilution with water gives a dispersion.

iii) Emulsifiable concentrates (EC).

15-70 wt.% diaminotriazine compound of formula (I) according to the invention and 5-10 wt.% emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-immiscible organic solvent (for example, an aromatic hydrocarbon) to 100 wt.% . Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt.% diaminotriazine compound of formula (I) according to the invention and 1-10 wt.% emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt.% water-immiscible organic solvent (for example, an aromatic hydrocarbon ). This mixture is added to water up to 100 wt.% using an emulsifying device and converted into a homogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS).

In a ball mill with an agitator, 20-60% by weight of the diaminotriazine compound of formula (I) according to the invention is ground with the addition of 2-10% by weight of dispersants and wetting agents (for example, sodium lignosulfonate and ethoxylated alcohol), 0.1-2% by weight. thickener (for example, xanthan gum) and water up to 100 wt.% to obtain a thin suspension of the active substance. Dilution with water gives a stable suspension of the active substance. For an FS type composition, up to 40 wt.% of a binder (for example, polyvinyl alcohol) is added.

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

50-80% by weight of the diaminotriazine compound of formula (I) according to the invention is finely ground with the addition of dispersants and wetting agents (for example, sodium lignosulfonate and ethoxylated alcohol) to 100% by weight and water-dispersible or water-soluble granules are obtained using technical devices (for example, an extruder , spray column, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

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

50-80 wt.% diaminotriazine compound of formula (I) according to the invention is 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, ethoxylated alcohol) and solid carrier (for example, silica gel) up to 100 wt.%. Dilution with water gives a stable dispersion or solution of the active substance.

- 80 044989 viii) Gel (GW, GF).

In a ball mill with an agitator, 5-25 wt.% diaminotriazine compound of formula (I) according to the invention is ground with the addition of 3-10 wt.% dispersants (for example, sodium lignosulfonate), 1-5 wt.% thickener (for example, carboxymethylcellulose) and water up to 100 wt.% to obtain a thin suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

iv) Microemulsion (ME).

5-20% by weight of the diaminotriazine compound of formula (I) according to the invention is added to 5-30% by weight of a mixture of organic solvents (for example, fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a mixture of surfactants (for example, ethoxylated alcohol and arylphenol ethoxylate) and water up to 100%. This mixture is stirred for 1 hour until a spontaneously thermodynamically stable microemulsion is obtained.

iv) Microcapsules (CS).

An oil phase containing 5-50 wt.% diaminotriazine compound of formula (I) according to the invention, 0-40 wt.% water-immiscible organic solvent (for example, an aromatic hydrocarbon), 2-278 wt.% acrylic monomers (for example, methyl methacrylate, methacrylic acid and di- or triacrylate) are dispersed in an aqueous solution of a protective colloid (for example, polyvinyl alcohol). Radical polymerization is initiated using a radical initiator, which leads to the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5-50 wt.% of the azine of formula (I) according to the invention, 0-40 wt.% water-immiscible organic solvent (for example, an aromatic hydrocarbon) and an isocyanate monomer (for example, diphenylmethane-4,4'- diisocyanate), dispersed in an aqueous solution of a protective colloid (for example, polyvinyl alcohol). The addition of a polyamine (eg hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomers is up to 1-10 wt.%. Wt.% relative to the total weight of the CS composition.

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

1-10% by weight of the diaminotriazine compound of formula (I) according to the invention is finely ground and thoroughly mixed with a solid carrier (eg finely divided kaolin) to 100% by weight.

x) Granules (GR, FG).

0.5-30% by weight of the diaminotriazine compound of formula (I) according to the invention is finely ground and mixed with a solid carrier (eg silicate) to 100% by weight.

Granulation is carried out by extrusion, spray drying or fluidized bed. xi) Ultra Low Volume (UL) Liquids.

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

Agrochemical compositions of types i)-xi) may optionally contain additional auxiliary agents, such as 0.1-1 wt.% bactericides, 5-15 wt.% antifreeze, 0.1-1 wt.% defoamers and 0.1-1 wt.% dyes.

Agrochemical compositions typically contain from 0.01 to 95%, preferably from 0.1 to 90% and in particular from 0.5 to 75% by weight of a diaminotriazine compound of formula (I). The diaminotriazine 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), Suspension Emulsions (SE), Flowable Concentrates (FS), Dry Treatment Powders (DS), Water Dispersible Suspension Treatment Powders (WS), Water Soluble Powders (SS), Emulsions (ES), Emulsifiable Concentrates ( EC) and gels (GF) are commonly used for the purpose of processing plant propagation materials, especially seeds. These agrochemical compositions, after two to tenfold dilution, provide concentrations of the active substance from 0.01 to 60 wt.%, preferably from 0.1 to 40 wt.%, in ready-to-use preparations. Treatment can be carried out before or during sowing.

Methods of applying diaminotriazine compounds of formula (I) or agrochemical compositions thereof to plant propagation material, especially seeds, include methods of treating the propagation material, such as dressing, coating, granulating, dusting, drenching and furrow application. Preferably, Compound I or compositions thereof are respectively applied to the plant propagation material by a method in such a way that germination is not promoted, for example by dressing, granulating, coating and dusting the seeds.

Various types of oils, wetting agents, adjuvants, fertilizers, micronutrients or additional pesticides (eg herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the diaminotriazine compounds of formula (I) or to agrochemical compositions containing them, as a premix or, if necessary, in advance of use (tank mixture). These agents can be mixed with the agrochemical compositions according to the invention in a weight ratio of from 1:100 to 100:1, preferably from 1:10 to 10:1.

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The user applies the diaminotriazine compounds of formula (I) according to the invention or agrochemical compositions containing them, typically from a pre-metered device, backpack sprayer, spray tank, spray plane or irrigation system. Typically, the agrochemical composition is diluted with water, buffer and/or additional auxiliary agents to the desired applied concentration and thereby obtain a ready-to-use spray liquid or agrochemical composition according to the invention. Typically, from 20 to 2000 liters, preferably from 50 to 400 liters of ready-to-use spray liquid are applied per hectare of agricultural usable area.

According to one embodiment, either the individual components of the agrochemical composition according to the invention, or partially mixed components, for example, components containing diaminotriazine compounds of formula (I), can be mixed by the user in a spray tank and, if necessary, additional auxiliary agents and additives can be added .

In a further embodiment, the individual components of the agrochemical composition according to the invention, such as parts of a kit or parts of a binary or ternary mixture, can be mixed by the user in a spray tank and, if necessary, additional auxiliary agents and additives can be added.

In a further embodiment, either the individual components of the agrochemical composition according to the invention, or partially mixed components, for example, components containing diaminotriazine compounds of formula (I), can be applied together (for example, after tank mixing) or sequentially.

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

Diaminotriazine compounds of formula (I) or agrochemical compositions containing diaminotriazine compounds of formula (I) are very effective in controlling vegetation in non-agricultural areas, especially at high application rates. They act against broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant harm to cereals. This effect is observed mainly at low application rates.

Diaminotriazine compounds of formula (I) or agrochemical compositions containing them are applied to plants, mainly by spraying onto leaves or by applying to the soil in which the plant seeds have been sown. In this case, the application can be carried out using, for example, water as a carrier, using conventional spraying methods, using a spray liquid in an amount of from about 100 to 1000 l/ha (for example, from 300 to 400 l/ha). The diaminotriazine compounds of formula (I) or agrochemical compositions containing them can also be applied using low-volume or ultra-low-volume methods, or in the form of microgranules.

The use of diaminotriazine compounds of formula (I) or agrochemical compositions containing them can be carried out before, during and/or after the appearance of undesirable plants.

The diaminotriazine compounds of formula (I) or agrochemical compositions containing them can be applied pre-, post-emergence or before sowing or simultaneously with sowing of the crop. It is also possible to apply diaminotriazine compounds of formula (I) or agrochemical compositions containing them to crop seeds pre-treated with diaminotriazine compounds of formula (I) or agrochemical compositions containing them. If the active ingredients are less well tolerated by certain crops, application techniques may be used in which the herbicidal compositions are sprayed using spray equipment such that, as far as possible, they do not come into contact with the leaves of sensitive crops while the active ingredients reach leaves of unwanted plants growing below, or the surface of open ground (method of post-emergence targeted treatment, method of treatment during or after the last cultivation).

In a further embodiment, diaminotriazine compounds of formula (I) or agrochemical compositions containing them can be applied by seed treatment. Seed treatment includes essentially all techniques that are familiar to one skilled in the art (seed dressing, seed coating, seed dusting, seed drenching, seed filming, seed multi-coating, seed encrusting, seed drip treatment, and pelleting of seeds), based on diaminotriazine compounds of formula (I) or agrochemical compositions obtained 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. In this case, preferably the term seeds describes grains and seeds. As seeds, you can use the seeds of the useful plants mentioned above, as well as the seeds of transgenic plants or plants obtained by conventional crossing methods.

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When used for plant protection, the amounts of active substances used, i.e. diaminotriazine compounds of formula (I), without auxiliary agents of the composition are, depending on the type of action desired, 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 particular from 0.05 to 0.5 kg per ha.

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

In another preferred embodiment of the invention, the application rates of the diaminotriazine compounds of formula (I) according to the present invention (total amount of diaminotriazine compound 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 purpose of control, season, target plants and growth stage.

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

In another preferred embodiment of the invention, the application rate of diaminotriazine compounds (I) is 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 dusting, coating or soaking the seeds, quantities of active substance 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 kilograms of plant propagation material (preferably seeds).

In another embodiment of the invention, the amounts of active substances, ie diaminotriazine compounds of formula (I), used for seed treatment are typically 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 area being treated and the desired effect. The amounts typically used in protecting 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 being treated.

Depending on the method of application in question, the diaminotriazine compounds of formula (I) or agrochemical compositions containing them can additionally be used in a number of additional crops to eliminate unwanted plants. Examples of suitable crops are: Allium sera, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, 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, Glyc ine max , Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa , Musa spec, Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, 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, Hordeum vulgare, Juglans regia, 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, canola, cotton, potatoes, peanuts or perennial crops.

The diaminotriazine compounds of formula (I) according to the invention or agrochemical compositions containing them can also be used in relation to genetically modified plants. The term genetically modified plants is understood to mean plants the genetic material of which 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, wherein such modification(s) cannot be obtained by crossbreeding, mutagenesis or solely natural recombination. In many cases, an individual genetically modified plant is a plant that has received its genetic modification(s) by inheritance through natural crossing or propagation from a parent plant whose genome has been directly manipulated using recombinant DNA techniques. By default, 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 including amino acid mutation(s) that allows, reduces or promotes glycosylation or polymer attachment such as prenylation, acetylation, farnesylation or addition of a PEG moiety.

Also included are plants that have been modified by crossing, mutagenesis, or genetic engineering, for example, that have been rendered resistant to application of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; whitening herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylureas or imidazolinones; enolpyruvylshikimate 3-phosphate intase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACC) inhibitors; or oxynyl (i.e., bromoxynyl or ioxynyl) herbicides, as a result of conventional crossbreeding or genetic engineering methods; in addition, plants that have been rendered resistant to multiple classes of herbicides by multiple genetic modifications, such as resistance to both glyphosate and glufosinate, or both glyphosate and another class of herbicide, such as ALS inhibitors, HPPD inhibitors, auxin herbicides or ACCase inhibitors. These herbicide resistance 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 literature cited therein. Some cultivated plants have acquired resistance to herbicides as a result of mutagenesis and conventional crossing methods, for example, Clearfield® rapeseed (canola, BASF SE, Germany) is resistant to imidazolinones, such as imazamox, or ExpressSun® sunflower (DuPont, USA) is resistant to sulfonylureas , for example, tribenuron. Genetic engineering techniques have been used to make crops such as soybeans, cotton, corn, beets and canola resistant to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are under development or available for purchase under branded or trade names. brands RoundupReady® (glyphosate-resistant, Monsanto, USA), Cultivance® (imidazolinone-resistant, BASF SE, Germany) and LibertyLink® (glufosinate-resistant, Bayer CropScience, Germany).

In addition, also included are plants which, by using recombinant DNA techniques, are capable of synthesizing one or more insecticidal proteins, especially those known from the genus Bacillus bacteria, especially from Bacillus thuringiensis, such as delta endotoxins, for example CryIA(b), CryIA (c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Oy9c; vegetative insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria-colonized nematodes, such as Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins or other insect-specific neurotoxins; toxins produced by fungi such as Streptomycetes toxins, plant lectins such as pea or barley lectin; 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 metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors or HMG-CoA reductase; ion channel blockers such as sodium or calcium channel blockers; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the context of the present invention, these insecticidal proteins or toxins should clearly include pretoxins, fusion proteins, truncated or otherwise modified proteins. Fusion proteins are characterized by a new combination of protein domains (see, for example, WO 02/015701). Additional examples of such toxins or genetically 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 451878, WO 03/18810 and WO 03/52073. Methods for producing such genetically modified plants are usually known to one skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in genetically modified plants give plants that produce these proteins resistance to pests from all taxonomic groups of arthropods, especially beetles (Coeloptera), diptera (Diptera), and butterflies (Lepidoptera), and nematodes (Nematoda). . Genetically modified races

- 84 044989 tenias capable of synthesizing one or more insecticidal proteins are, for example, the plants described in the publications mentioned above, some of which are commercially available, such as YieldGard® (maize crops that produce the Cry1Ab toxin), YieldGard® Plus (corn cultivars that produce the toxins Cry1Ab and Cry3Bb1), Starlink® (corn cultivars that produce the Cry9c toxin), Herculex® RW (corn cultivars that produce Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-M-acetyltransferase [PAT]); NuCOTN® 33B (cotton crops that produce CrylAc toxin), Bollgard® I (cotton crops that produce Cry1Ac toxin), Bollgard® II (cotton crops that produce Cry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars that produce VIPtoxin) NewLeaf® (potato cultivars that produce Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Btll (e.g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (maize cultivars that produce CrylAb toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (maize crops that produce a modified type of Cry3A toxin, cf. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (maize crops that produce the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium ( cotton cultivars that produce a modified type of CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (maize cultivars that produce 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 to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called pathogenesis-related proteins (PR proteins, see, for example, EP-A 392 225), plant disease resistance genes (for example, potato cultivars expressing resistance genes against Phytophthora infestans, derived from Mexican wild potato, Solatium bulbocastanum) or T4-lysozyme (for example, potato cultivars capable of synthesizing such proteins with increased resistance against bacteria such as Erwinia amylovora). Methods for producing such genetically modified plants are usually known to a person skilled in the art and are described, for example, in the publications mentioned above.

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

In addition, plants are included which, through the use of recombinant DNA techniques, contain modified amounts of ingredients or new ingredients, in particular for improving human or animal nutrition, for example, oilseeds producing long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids, health promoting (for example, Nexera® rapeseed, Dow AgroSciences, Canada).

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

A further embodiment of the invention is a method of controlling unwanted vegetation which includes contacting a herbicidally active amount of at least one compound of formula (I) as defined above with plants, their surroundings or seeds.

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

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

HPLC-MS = high-performance liquid chromatography-coupled mass spectrometry. HPLC column:

column RP-18 (Chromolith Speed ROD from Merck KgaA, Germany), 50x4.6 mm;

mobile phase: acetonitrile + 0.1% trifluoroacetic acid (TPA)/water + 0.1% TFA using a gradient from 5:95 to 100:0 over 5 min at 40°C, flow rate 1.8 ml/min.

MS: quadrupole electrospray ionization, 80 V (positive method).

The following abbreviations were used:

TFA: trifluoroacetic acid,

OH: cyclohexane, EtOAc: ethyl acetate, THF: tetrahydrofuran, MeOH: methanol,

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HPLC: high performance liquid chromatography,

LC: liquid chromatography,

MS: mass spectrometry.

A. Examples of receipt.

Example 1. N4-(2-Benzyloxy-6-fluorophenyl)-6-(1-methoxy-1-methylethyl)-1,3,5-triazine-2,4-diamine.

Step 1. 1-Benzyloxy-3-fluoro-2-nitrobenzene

K2CO3 (25.3 g, 183 mmol, 1.2 eq) was added to a solution of 3-fluoro-2-nitrophenol (24.0 g, 153 mmol, 1.0 eq) in 100 mL DMF. Benzyl bromide (26.1 g, 153 mmol, 1.0 eq.) was added to the suspension at room temperature. The mixture was stirred for 18 hours overnight. Water was added to the reaction mixture to dissolve the salts. The solution was extracted three times with 100 ml EtOAc. The combined organic layers were washed with water, dried with Na ₂ SO ₄ and then evaporated. The solid residue was used without further purification in the next step.

LC/MS RT: 1.204. LC/MS (m/z): no ionization of the molecule was observed.

1H-NMR (400 MHz, CDCl ₃ ) δ 5.2 (s, 2H), 6.8 - 6.9 (m, 2H), 7.3 - 7.4 (m, 6H).

Stage 2. 2-Benzyloxy-6-fluoroaniline

Zinc powder (52.9 g, 809 mmol, 4.0 eq.) was suspended in 400 ml of acetic acid. 1-Benzyloxy-3-fluoro-2-nitrobenzene (50 g, 202 mmol, 1.0 eq.) dissolved in 80 ml EtOAc was added slowly so that the temperature of the reaction mixture did not exceed 40°C. The mixture was stirred over the weekend at ambient temperature and then diluted with 300 ml EtOAc. After filtration, water was added. The organic layer was washed with saturated NaHCO ₃ solution and then evaporated. The crude material was purified by column chromatography (silica, cyclohexane/EtOAc) to give the desired product (29.7 g, 67% yield) as a light yellow oil. LC/MS RT: 1.051. LC/MS (m/z): 217.9 [M+H+].

1H-NMR (400 MHz, CDCls) δ 3.2 - 4.1 (b, 2H), 5.08 (s, 2H), 6.55 - 6.75 (m, 3H), 7.3 - 7 .5 (m, 5N).

Step 3. 4-(1-methoxy-1-methylethyl)-6-methylsulfanyl-1,3,5-triazin-2-amine

2-Methoxy-2-methylpropanoic acid (5.4 g, 45.7 mmol, 1.01 eq.) was dissolved in 10 ml CH ₂ Cl ₂ . After adding 3 drops of DMF, oxalyl dichloride (5.8 g, 45.7 mmol, 1.01 eq) was added at ambient temperature. After 1 hour, when gas evolution was no longer observed, the solution was slowly added to a solution of 1-carbamimidoyl-2-methyl-isothiourea hydroiodide (11.8 g, 45.4 mmol, 1.0 eq.) and triethylamine (13.78 g , 136 mmol, 3.0 eq.) in 70 ml of dioxane. After stirring at 60°C for 4 hours, water and EtOAc were added. The organic phase was separated, dried over Na ₂ SO ₄ and evaporated, obtaining 9.4 g of crude product, which was used without further purification in the next step.

LC/MS RT: 0.742. LC/MS (m/z): 215.1 [M+H+].

1H-NMR (400 MHz, DMSO-d6) δ 1.41 (d, 6H), 2.44 (s, 3H), 3.05 (s, 3H), 7.53 (d, 2H).

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Step 4. 4-Chloro-6-(1-methoxy-1-methylethyl)-1,3,5-triazin-2-amine

Via a solution of 4-(1-methoxy-1-methylethyl)-6-methylsulfanyl-1,3,5-triazin-2-amine (9.4 g, 43.9 mmol, 1.0 eq.) in 100 ml EtOAc /CHCl ₃ , chlorine gas was bubbled at ambient temperature for 30 minutes. Due to incomplete conversion of the starting material, chlorine gas was introduced for an additional 30 min. After this period, the solution was purged with N2 gas and concentrated. The solid residue was treated with water, the precipitated solid was filtered and dried, obtaining 5.7 g of crude product, which was used in the next step.

LC/MS RT: 0.736. LC/MS (m/z): 203.0 [M+H+] 1.40 (s, 6H), 3.07 (s, 3H), 8.12, (d, 2H).

1H-NMR (400 MHz, DMSO-d ₆ ) δ

Step 5. N4-(2-Benzyloxy-6-fluorophenyl)-6-(1-methoxy-1-methylethyl)-1,3,5-triazine-2,4-diamine

2-Benzyloxy-6-fluoroaniline (400 mg, 1.8 mmol, 1.0 eq.) and 4-chloro-6-(1-methoxy-1-methylethyl)-1,3,5triazin-2-amine (373 mg, 1.8 mmol, 1.0 eq.) was suspended in 5 ml of dioxane. Hydrogen chloride in dioxane (4.1 ml, 4.0 molar solution, 3.0 eq.) was added. The mixture was heated to 90°C for 2 hours and then cooled to ambient temperature. After adding water and EtOAc, the organic phase was separated, dried over Na ₂ SO ₄ and evaporated to give the crude product, which was purified by column chromatography (silica, cyclohexane/EtOAc) to give the desired product (163 mg, 23% yield).

LC/MS RT: 0.921. LC/MS (m/z): 384.0 [M+H+].

1H-NMR (400 MHz, DMSO-Y6) δ 2.5 (s, 6H), 3.3 (s, 3H), 5.1 (s, 2H), 6.75 - 6.9 (m, 3H ), 6.93 (d, 1H), 7.15-7.35 (m, 6H).

Example 2 N-(2-Benzyloxy-6-fluorophenyl)-6-(1-fluoro-2-methylpropyl)-1,3,5-triazine-2,4-diamine.

Step 1. 1-(2-Benzyloxy-6-fluorophenyl)-3-carbamimidoyl-guanidine hydrochloride o

g x HCI

2-Benzyloxy-6-fluoroaniline (20 g, 92 mmol, 1.0 eq.) and 1-cyanoguanidine (9.3 g, 110.5 mmol, 1.2 eq.) were mixed in 150 ml of acetonitrile. Hydrochloric acid (10.7 g, 37.5 wt%, 1.2 eq) was added and the mixture was heated to 75°C for 6 hours. After cooling to ambient temperature, the precipitated solid was filtered and washed with acetonitrile and pentane. The solid was dried in vacuo to obtain 23.7 g of HCl salt. The free base can be prepared by treatment with sodium hydroxide solution and extraction with an aqueous mixture of EtOAc. LC/MS RT: 0.761. LC/MS (m/z): 301.9 [M+H+].

Step 2. N4-(2-Benzyloxy-6-fluorophenyl)-6-(1-fluoro-2-methylpropyl)-1,3,5-triazine-2,4-diamine

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2-Fluoro-3-methylbutanoic acid (1.1 g, 9.31 mmol, 1.0 eq.) was dissolved in 30 ml CH ₂ Cl ₂ . At -78°C, DAST (3.0 g, 18.6 mmol, 2.0 eq.) was slowly added. After self-warming to ambient temperature overnight, the mixture was added to a solution of 1-(2-benzyloxy-6-fluorophenyl)-3carbamidoylguanidine and triethylamine in 60 ml of dioxane. The reaction mixture was stirred at 50°C for 3 hours. After cooling to ambient temperature, the mixture was poured into water and extracted with additional CH ₂ Cl ₂ . After evaporation of the solvent, the crude product was purified by column chromatography (silica, cyclohexane/EtOAc) to obtain the desired product (45 mg, 1.3% yield) as a white solid.

LC/MS RT: 1.061. LC/MS (m/z): 385.9 [M+H ⁺ ].

'H-NMR (500 MHz, DMSO-a ₆ ) 0.85 (b, 6H), 2.1 - 2.3 (b, 1H), 4.6 - 4.85 (d, 1H), 5, 1 (s, 2H), 6.8 - 7.4 (m, JN), 8.75 (w, 1H).

The connections shown in the table below. 3 (examples 3-263) was prepared similarly to the examples given above

Table 3

Etc. No. r ² r ³ r ⁴ R ^{a Rbl} R ^b2 R ^b3 r ⁶ r ⁷ r ⁷ MS HPLC 3. CFMe ₂ F H H H (3,5 - dimethyl phenyl)methyl 1.131 399.9 4. CFMe ₂ F H H H benzyl 0.997 372.2 5. 1-fluorocyclopentyl F H H H benzyl 1.051 398.1 6. CFMe ₂ F H H H (4-fluorophenyl)methyl 1,000 390.1 7. CFMe ₂ F H H H (4-nitrophenyl)methyl 0.979 417.1 8. CFMe ₂ F H H H [4-(trifluoromethyl)phenyl]methyl 1,082 440.1 9. CFMe ₂ F H H H p-tolylmethyl 1.04 386.1 10. CFMe ₂ F H H H (3-methoxyphenyl)methyl 0.993 402.1 AND. CFMe ₂ F H H H (3-fluorophenyl)methyl 0.999 390.1 12. 1-fluorocyclopentyl F H H H (4-fluorophenyl)methyl 1.035 416.1 13. 1-fluorocyclopentyl F H H H (4-nitrophenyl)methyl 1.022 443.0 14. 1-fluorocyclopentyl F H H H (3-methoxyphenyl)methyl 1,074 412.1 15. 1-fluorocyclopentyl F H H H p-tolylmethyl 1.028 428.1 16. 1-fluorocyclopentyl F H H H (4-methoxyphenyl)methyl 1.025 428.1 17. 1-fluorocyclopentyl F H H H [4-(trifluoromethyl)phenyl]methyl 1.114 466.1 18. 1-fluorocyclopentyl F H H H (3-fluorophenyl)methyl 1.035 416.1 19. 1-fluorocyclopentyl F H H H (2-fluorophenyl)methyl 1.034 416.1 20. CFMe ₂ F H H H (4-methoxyphenyl)methyl 0.989 402.1 21. CFMe ₂ F H H H 3-pyridylmethyl 0.707 373.1 22. CFMe ₂ F H H H 3-thienylmethyl 0.961 378.1 23. CFMe ₂ F H H H 1-phenylethyl 1.023 386.2 24. CFMe ₂ F H H H [3-(trifluoromethyl)phenyl1methyl 1.061 440.1 25. CFMe ₂ F H H H (3-nitrophenyl)methyl 0.981 417.1 26. CFMe ₂ F H H H m-tolylmethyl 1.052 386.1 27. CFMe ₂ F H H H (2-fluorophenyl)methyl 1.007 390.0 28. CFMe ₂ F H H H (2-nitrophenyl)methyl 0.994 417.1 29. CFMe ₂ F H H H |'2-(trifluoromethyl)phenyl1methyl 1,093 440.0 thirty. CFMe ₂ F H H H o-tolylmethyl 1.038 386.1

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31. 1-fluorocyclohexyl F H H H benzyl 1,092 412.1 32. 1-methylcyclohexyl F H H H benzyl 1,064 408.1 33. t-Vee F H H H benzyl 0.976 368.0 34. 1-hydroxypropyl F H H H benzyl 0.882 370.0 35. 1-fluoropropyl F H H H benzyl 1.013 372.0 36. CFMe ₂ F H H H thiazol-2-ylmethyl 0.862 379.0 37. CFMe ₂ F H H H (2-methylthiazol-5-yl)methyl 0.823 393.0 38. CFMe ₂ F H H H (5-methox icarbonyl-2furyl)methyl 0.912 420.0 39. CFMe ₂ F H H H (2-chlorothiazol-5-yl)methyl 1.035 412.0 40. CFMe ₂ F H H H (3-methylisoxazol-5-yl)methyl 0.871 377.0 41. CFMe ₂ F H H H 1,3,4-oxadiazol-2-ylmethyl 0.76 364 42. CFMe ₂ F H H H (3-cyclopropyl-1,2,4-oxadiazol5-yl)methyl 0.926 404 43. CFMe ₂ F H H H (3,5-d iforophenyl)methyl 1,048 408 44. CFMe ₂ F H H H (3-bromophenyl)methyl 1,081 449.9 45. CFMe ₂ F H H H (3,4-difluorophenyl)methyl 1.008 408 46. CFMe ₂ F H H H (3-iodophenyl)methyl 1.058 497.9 47. CFMe ₂ F H H H (3-chlorophenyl)methyl 1.029 406 48. CFMe ₂ F H H H (3-chloro-4-methoxy-phenyl)methyl 1.056 435.9 49. CFMe ₂ F H H H (3-chloro-5-fluorophenyl)methyl 1.095 424 50. CFMe ₂ F H H H (4-methoxycarbonyloxazol-2yl)methyl 0.847 421.1 51. CFMe ₂ F H H H (5-methyl-1,3,4-oxad iazol-2yl)methyl 0.784 378 52. 1-methylcyclobutyl F H H H benzyl 1.008 380.1 53. CFMe ₂ F H H H (3-chloro-5-methoxy-phenyl)methyl 1,082 435.9 54. CFMe ₂ F H H H (3-fluoro-5-methoxy-phenyl)methyl 1.039 420.0 55. CFMe ₂ F H H H (3-chloro-4-fluorophenyl)methyl 1,070 424.0 56. CFMe ₂ F H H H (3-fluoro-4-methyl-phenyl)methyl 1,070 404.0 57. CFMe ₂ F H H H (3,5-dichlorophenyl)methyl 1,090 440.0 58. CFMe ₂ F H H H [ 3 -(difluoromethox and)phenyl]methyl 1.016 438.1 59. CFMe ₂ F H H H (3-methylsulfonylphenyl)methyl 0.888 449.9 60. CFMe ₂ F H F H benzyl 1.008 390.0 61. CFMe ₂ F Br H H benzyl 1.008 380.1 62. CFMe ₂ F H H H (3-fluoro-4-methoxy-phenyl)methyl 1.001 420.0 63. CFMe ₂ F H H H [3-(difluoromethoxy)-5-fluorophenyl]methyl 1.061 456.1 64. CFMe ₂ F H H H thiazol-5-ylmethyl 0.816 378.9 65. 1-fluoro-2-methyl-propyl F H H H benzyl 1.061 385.9 66. CFMe ₂ F H H H (3-methyl-1,2,4-oxadiazol-5yl)methyl 0.842 378.0 67. 1 -fluorocyclopent-3 -ey-1 -yl F H H H benzyl 1.037 396.0 68. CFMe ₂ F H H H (3-chloro-4-methylsulfanylphenyl)methyl 1,100 452.0 69. CFMe ₂ F F F H benzyl 1,096 408.0 70. CFMe ₂ F H H H oxazol-2-ylmethyl 0.819 363 71. CFMe ₂ F H H H (4-methoxycarbonylthiazol-2yl)methyl 0.877 437.0 72. CFMe ₂ F H H F benzyl 1,041 390.0 73. CFMe ₂ F H H H (3,5-difluoro-4-methoxyphenyl)methyl 1,046 438.1 74. CFMe ₂ F H H H (2,3,5-trifluorophenyl)methyl 1,042 426.0 75. CFMe ₂ F H H H (3,5-dimethoxyphenyl)methyl 1.012 432.0 76. 1 -(fluoromethyl)cyclopropyl F H H H benzyl 0.961 383.9 77. 1-fluorobutyl F H H H benzyl 1,091 386.0 78. CFMe ₂ F H H H (2,6-dichlorophenyl)methyl 1.067 440.0 79. CFMe ₂ F H H H (3-chloro-4-ethoxy-phenyl)methyl 1.103 450.1

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80. CFMe ₂ F H H H (3-isopropylphenyl)methyl 1.152 414.1 81. CFMe ₂ Br H H H benzyl 1.01 433.9 82. CFMe ₂ H H H H benzyl 1,060 354.0 83. CFMe ₂ F H H H difluoro(phenyl)methyl 1,098 408.4 84. CFMe ₂ F H H H (3-cyanophenyl)methyl 0.961 397.0 85. CFMe ₂ Cl H H H benzyl 1.035 388.4 86. CFMe ₂ F H H H (4-vinylphenyl)methyl 1,084 398.4 87. CFMe ₂ F H H H [4-(methylcarbamoyl)phenyl]methyl 0.84 429.0 88. CFMe ₂ F H H H (4-methoxycarbonylphenyl)methyl 0.986 430.1 89. CFMe ₂ F H H H (3-methoxycarbonylphenyl)methyl 0.984 430.1 90. CFMe ₂ F H H H 2-pyridylmethyl 0.739 373.0 91. SMegOMe F H H H benzyl 0.943 384.1 92. CFMe ₂ F H H H 4-pyridylmethyl 0.675 372.9 93. CFMe ₂ F H H H (3-carboxyphenyl)methyl 0.880 416.0 94. CFMe ₂ F H H H (4-ethylphenyl)methyl 1.114 400 95. CFMe ₂ F H H H (3,4-dimethylphenyl)methyl 1,087 400.0 96. CF ₂ Me F H H H benzyl 1,088 376.0 97. CFMe ₂ F F F H (3-fluorophenyl)methyl 1.067 425.9 98. CFMe ₂ F F F H (3-methoxyphenyl)methyl 1.063 438.0 99. CFMe ₂ F H H H (2,6-d iforophenyl)methyl 1.067 425.9 100. CFMe ₂ F H H H (2-methoxyphenyl)methyl 0.999 402.0 101. CFMe ₂ F H H H [4-(difluoromethyl)phenyl]-difluoromethyl 1,087 457.9 102. CFMe ₂ F H H H (3-fluoro-2-methyl-phenyl)methyl 1.023 403.9 103. CFMe ₂ F H H H (4-carboxyphenyl)methyl 0.886 416.0 104. CFMe ₂ F H H H (4-chlorophenyl)-difluoromethyl 1.15 442.0 105. CFMe ₂ F H H H (5-methoxycarbonyl-3 thienyl)methyl 0.977 436.0 106. CFMe ₂ F H H H (5-methyl-3-thienyl)methyl 1.033 392.0 107. CFMe ₂ F H H H (2-chloro-3-thienyl)methyl 1.047 412.0 108. CFMe ₂ F F H H benzyl 1.056 390.0 109. CFMe ₂ F H H H (3-fluoro-2-methoxycarbonylphenyl)methyl 1.027 448.0 110. CFMe ₂ F H H H (5-chloro-3-thienyl)methyl 1,073 411.9 111. CFMe ₂ F H H H (4-methyl-3-thienyl)methyl 1.045 391.9 112. CFMe ₂ F H H H (2,5-dichloro-3-thienyl)methyl 1.158 445.9 FROM. CFMe ₂ F H H H benzyl 1.063 388.0 114. SMegOMe F H H H (3-fluorophenyl)methyl 0.926 401.9 115. SMegOMe F H H H (3-methoxyphenyl)methyl 0.924 414.0 116. CFMe ₂ F F F H difluoro(phenyl)methyl 1.171 444.0 117. SMegOMe F H H H difluoro(phenyl)methyl 0.971 420.1 118. CFMe ₂ F H H H benzyl 0.969 420 119. CFMe ₂ F H H H (5-acetyl-3-thienyl)methyl 0.898 420.0 120. CFMe ₂ F H H H (5-chloro-2-thienyl)methyl 1,046 411.9 121. CFMe ₂ F H H H (2-cyano-3-thienyl)methyl 0.942 402.9 122. CFMe ₂ F H H H (2-cyano-3-fluorophenyl)methyl 0.977 414.9 123. CFMe ₂ F H H H benzyl 0.909 403.9 124. CFMe ₂ F H H H (5-cyano-3-thienyl)methyl 0.939 402.9 125. CFMe ₂ F H H H (2,5-dimethyl-3-thienyl)methyl 1,068 405.9 126. CFMe ₂ F H H H (4-cyano-3-thienyl)methyl 0.903 402.9 127. CFMe ₂ H F H H benzyl 1.153 371.9 128. CFMe ₂ CN H H H benzyl 0.98 379 129. CFMe ₂ F F F H difluoro(3-fluorophenyl)methyl 1.193 461.9 130. CFMe ₂ F H H H difluoro(3-fluorophenyl)methyl 1,098 425.9 131. SMegOMe F H H H difluoro(3-fluorophenyl)methyl 0.998 437.9 132. CFMe ₂ F H H H (3-isopropoxyphenyl)methyl 1.101 430.0 133. CFMe ₂ F H H H (3-isobutoxyphenyl)methyl 1.182 444.1 134. CFMe ₂ F H H H [3-(2,2,2- 1,096 470.0

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trifluoroethoxy)phenyl]methyl 135. SMegOMe F H H F benzyl 0.970 402.0 136. CFMe ₂ F H H H [3-(trifluoromethoxy)phenyl]methyl 1.108 456.0 137. CFMe ₂ F H H H (4-cyanophenyl)methyl 0.970 397.0 138. CFMe ₂ F H H H (4-chlorophenyl)methyl 1,064 405.9 139. CFMe ₂ F H H F (3-methoxyphenyl)methyl 1.038 420.0 140. CFMe ₂ F H H F (4-ethylphenyl)methyl 1.148 418.0 141. CFMe ₂ F H H F p-tolylmethyl 1.053 404.0 142. CFMe ₂ F H H F difluoro(phenyl)methyl 1,068 426.0 143. CFMe ₂ F H H H (4-isopropylphenyl)methyl 1.147 414.1 144. CFMe ₂ F H H F (2-chlorothiazol-5-yl)methyl 0.985 430.8 145. CFMe ₂ F H H H [3 -(cyclopropylmethoxy)phenyl]methyl 1.109 442.0 146. CFMe ₂ F H H H (3-{tert}-butoxyenyl)methyl 1.128 488.1 147. CFMe ₂ F H H H [3-(2,2difluoroethoxy)phenyl!methyl 1.047 452.1 148. CFMe ₂ F H H Cl benzyl 1,088 405.9 149. CFMe ₂ F H H H (3-ethoxyphenyl)methyl 1.056 416.1 150. CFMe ₂ F H H H [3-(2-methoxy-2-oxoethoxy)phenyl]methyl 1,070 without ionization 151. CFMe ₂ F H H H (3-acetoxyphenyl)methyl 0.981 429.9 152. 1-fluoro-2-methyl-prop-1-enyl F H H H benzyl 1.022 383.9 153. CFMe ₂ F H H H (1-methylimidazol-2-yl)methyl 0.659 375.9 154. CFMe ₂ F H H H 2-thienylmethyl 0.946 377.9 155. CFMe ₂ F F H F benzyl 1,086 408.0 156. CF ₂ Me F F F H benzyl 1.154 411.9 157. CFMe ₂ F H H H [ 3 -(cyclopropoxy)phenyl1 methyl 1.059 428.3 158. (~{E})-1-fluoro-3-methyl-but-1 - F H H H benzyl 1.179 397.9 enyl 159. 1-fluoro-2-methyl-prop-1-enyl F F F H benzyl 1,098 419.9 160. 1-fluoro-2-methyl-prop-1-enyl F H H F benzyl 1.038 401.9 161. CHFMe F H H H benzyl 0.989 357.9 162. CFMe2 F H H H (4-cyclopropylphenyl)methyl 1.119 412 163. CFMe2 F Br H F benzyl 1.166 469.7 164. CFMe2 F F H F (3-methoxyphenyl)methyl 1,086 437.9 165. CFMe2 F F H F (2,6-d iforophenyl)methyl 1,093 443.9 166. CFMe2 F H H F (4-cyclopropylphenyl)methyl 1.131 430.0 167. CFMe2 F H H F (2,6-d iforophenyl)methyl 1.032 425.9 168. 1-fluorovinyl F H H H benzyl 1,089 356.2 169. 1-fluorobutyl F F F H benzyl 1.179 422.0 170. 1-fluorobutyl F H H F benzyl 1.133 404.0 171. CHFMe F H H H difluoro(phenyl)methyl 1.054 393.9 172. CFMe2 F H H F (2-fluorophenyl)methyl 1,040 408.0 173. CFMe2 F H H F (2-methoxyphenyl)methyl 1,066 420.0 174. CFMe2 F H H F 3-thienylmethyl 1.017 396.0 175. CFMe2 F H H Me benzyl 1.029 385.9 176. CFMe2 F F H H (2-chloro-6-fluorophenyl)methyl 1,087 441.8 177. CFMe2 F H H H (2-chloro-6-fluorophenyl)methyl 1.036 423.9 178. CFMe2 F F H H (2-methoxyphenyl)methyl 1.124 438.0 179. 1-fluorobutyl F H H H difluoro(phenyl)methyl 1,160 421.9 180. CFMe2 F F H F (4-methoxyphenyl)methyl 1,089 438.1 181. CFMe2 F F H F o-tolylmethyl 1.122 422.0 182. CFMe2 F F H F m-tolylmethyl 1.142 422.0 183. CFMe2 F F H F p-tolylmethyl 1.133 422.1 184. 1-F-cPr F H H H benzyl 1.016 369.9 185. CFMe2 F F H H (3-methoxyphenyl)methyl 1.047 419.9 186. CFMe2 F F H H (4-methoxyphenyl)methyl 1,043 420.0

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187. 1-F-cPr F Η Η F benzyl 1,042 387.9 188. CFMe2 F Η F F benzyl 1,083 407.9 189. cyclopropyl(fluoro)methyl F Η Η F benzyl 1,070 401.9 190. 1-methoxyethyl F Η Η Η benzyl 0.926 369.9 191. 1-methoxyethyl F Η Η F benzyl 0.940 387.9 192. CFMe2 F Η Η F (4-methoxyphenyl)methyl 1.039 419.9 193. CFMe2 F Η Η F (4-ethoxyphenyl)methyl 1,100 433.9 194. i-Pr F Η Η Η benzyl 0.958 354.0 195. 1-chloroethyl F Η Η Η benzyl 1,069 374.0 196. CHFMe F Η Η F benzyl 1.001 375.9 197. 1-fluoro-2-methyl-prop-1-enyl F Η Η Η difluoro(phenyl)methyl 1.107 419.9 198. CFMe2 F F Η Η (2-methoxyphenyl)methyl 1.077 419.9 199. 1-fluorocyclopentyl F F Η F benzyl 1.141 433.9 200. τ-Bu F F Η F benzyl 1,074 403.9 201. 1-methylcyclobutyl F F Η F benzyl 1.063 416.0 202. cyclopentyl(fluoro)methyl F Η Η Η benzyl 1,144 412.0 203. CFMe2 F F Η F (2-fluorophenyl)methyl 1,089 425.9 204. CFMe2 F F Η F (3-fluorophenyl)methyl 1,094 426.0 205. CFMe2 F F Η F (4-fluorophenyl)methyl 1,096 426.0 206. CFMe2 F F Η F (2-chlorophenyl)methyl 1.136 441.8 207. CFMe2 F F Η F (4-chlorophenyl)methyl 1.142 441.8 208. CFMe2 F F Η F (2-isopropylphenyl)methyl 1.227 449.9 209. CHFMe F F Η F benzyl 1.054 394.0 210. CHFMe F F Η F (2-methoxyphenyl)methyl 1,090 424.0 211. CHFMe F F Η F (3-methoxyphenyl)methyl 1.056 424.0 212. CHFMe F F Η F (4-methoxyphenyl)methyl 1.054 424.0 213. CMe2OMe F F Η F benzyl 1.001 420.0 214. CMe2OMe F F Η F (2-methoxyphenyl)methyl 1.027 450.1 215. CMe2OMe F F Η F (3-methoxyphenyl)methyl 1.006 450.1 216. CFMe2 F F Η F (4-ethylphenyl)methyl 1.204 435.9 217. CFMe2 F F Η F (3-chlorophenyl)methyl 1.148 441.8 218. CFMe2 F F Η F (2-cyclopropylphenyl)methyl 1,196 447.9 219. CFMe2 F F Η F [3-(methoxymethyl)phenyl]methyl 1,096 451.9 220. CFMe2 F F Η F [4-(methoxymethyl)phenyl]methyl 1,089 451.9 221. CFMe2 F Η Η Η [4-(methoxymethyl)phenyl]methyl 1,000 416.0 222. CFMe2 F F Η Br benzyl 1.157 468.0 223. CFMe2 F Η Η Βγ benzyl 1.102 452.0 224. CFMe2 F F Η F [2-(methoxymethyl)phenyl]methyl 1.095 451.9 225. CMe2OMe F F Η F (4-methoxyphenyl)methyl 1.013 449.9 226. CMe2OMe F F Η F o-tolylmethyl 1,040 433.9 227. CMe2OMe F F Η F m-tolylmethyl 1.051 433.9 228. CMe2OMe F F Η F p-tolylmethyl 1.057 433.9 229. CHFMe F F Η F o-tolylmethyl 1,092 407.9 230. CHFMe F F Η F m-tolylmethyl 1.104 407.9 231. CHFMe F F Η F p-tolylmethyl 1.109 407.8 232. CFMe2 F F Η F (2-bromophenyl)methyl 1,150 486.0 233. 1-fluoro-3-methyl-butyl F Η Η Η benzyl 1.141 400.0 234. CFMe2 F F Η C1 benzyl 1,140 424.0 235. CFMe2 F Br Η Br benzyl 1,209 529.9 236. CFMe2 F F F F benzyl 1.138 426.0 237. 1-methoxyethyl F F Η F o-tolylmethyl 0.986 419.9 238. 1-methoxyethyl F F Η F m-tolylmethyl 1.009 419.9 239. 1-methoxyethyl F F Η F p-tolylmethyl 0.997 419.9 240. 1-methoxyethyl F F Η F (2-fluorophenyl)methyl 0.981 424.0 241. 1-methoxyethyl F F Η F (3-fluorophenyl)methyl 0.993 424.0 242. 1-methoxyethyl F F Η F (4-fluorophenyl)methyl 0.991 424.0 243. 1-methoxyethyl F F Η F (2-chlorophenyl)methyl 1.022 440.0 244. 1-methoxyethyl F F Η F (3-chlorophenyl)methyl 1,030 440.0 245. 1-methoxyethyl F F Η F (4-chlorophenyl)methyl 1.028 440.0 246. 1-chloro-1-methyl-ethyl F F Η F benzyl 1.215 423.9 247. 1-fluoro-1-methylpropyl F F Η F benzyl 1.128 421.9 248. СМе2ОМе F F Η F (2-fluorophenyl)methyl 1.015 438.0 249. СМе2ОМе F F Η F (3-fluorophenyl)methyl 1.023 438.0 250. СМе2ОМе F F Η F (4-fluorophenyl)methyl 1.023 438.0 251. СМе2ОМе F F Η F (2-chlorophenyl)methyl 1,050 454.0 252. СМе2ОМе F F Η F (3-chlorophenyl)methyl 1,060 454.1 253. СМе2ОМе F F Η F (4-chlorophenyl)methyl 1.058 454.0 254. i-Pr F F Η F benzyl 0.973 389.9 255. CHFMe F F Η F (2,6-dimethylphenyl)methyl 1.135 421.9 256. 1-fluorocyclohexyl F F Η F benzyl 1.208 448.1 257. CFMe2 F Η Η Η benzyl 1,046 369.9 258. 1-fluorocyclohexyl F Η Η CN benzyl 1,093 436.9 259. CFMe2 F Η Η CN benzyl 1,000 397.1 260. 1-fluorocyclopentyl Cl Η Η Br benzyl 1.186 494.0 261. CFMe2 Cl Η Η Br benzyl 1.143 468.0

B. Examples of use.

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

The culture containers used were plastic flower pots containing clay sand with approximately 3.0% humus as substrate. Seeds of experimental plants were sown separately for each species.

For pre-emergence treatments, active ingredients suspended or emulsified in water were applied directly after sowing using fine-distributing 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 caused uniform germination of the test plants unless it was disturbed by the active ingredients.

For post-emergence treatments, test plants were first grown to a height of 3 to 15 cm, depending on the plant species, and only then treated with active ingredients that were suspended or emulsified in water. To do this, test plants were either directly sown and grown in the same containers, or they were first grown separately as seedlings and transplanted into test containers a few days before treatment.

Depending on the species, plants were kept at temperatures of 10-25 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 assessed.

The assessment was carried out on a scale from 0 to 100. 100 means no plant emergence or complete destruction of at least above-ground parts, and 0 means no damage or normal growth. Moderate herbicidal activity is given at values of at least 60, good herbicidal activity is given at values of at least 70, and very good herbicidal activity is given at values of at least 85.

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

Bayer code Scientific name Russian name ABUTH Abutilon theophrasti Ropeman of Theophrastus ALOMY Alopercurus myosuroides Foxtail mousetail AMARE Amaranthus retroflexus Amaranth upturned APESV Apera spica-venti Regular broomstick CAPBP Capsella bursa-pastoris Shepherd's Purse CHE AL Chenopodium album White pigweed ECHCG Echinocloa crus-galli Common barnyard grass GERDI Geranium dissectum Geranium dissected LAMPU Lamium purpureum Purple lily LOLMU Lolium multiflorum Chaff multicolor MATIN Matricaria maritima Mayweed POAAN Poa annua Meadow bluegrass POLCO Polygonum convolvulus Convolvulus knotweed SETFA Setaria faberi Faber's bristlecone SETVI Setaria viridis Green foxtail STEM Stellaria media Chickweed average THLAR Thlaspi arvense Yarutka field VIOAR Viola arvensis Field violet

Example 4, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 5, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 98%, 100% and 98% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 6, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 9, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80%, 95%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 10, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crusgalli and Setaria faberi.

Example 11, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crusgalli and Setaria faberi.

Example 14, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 90% and 80% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 18, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 70%, 70%, 70% and 85% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

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Example 19, used for pre-emergence treatment at an application rate of 250 g/ha, showed

70%, 80% and 85% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus and Setaria faberi, respectively.

Example 20, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 98%, 100% and 95% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 22, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 23, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% and 75% herbicidal activity against Echinocloa crus-galli and Setaria faberi, respectively.

Example 26, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 80% and 70% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 27, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi.

Example 28, used as a post-emergence treatment at an application rate of 125 g/ha, showed 75%, 85% and 75% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria viridis, respectively.

Example 30, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 31, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 75% and 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Echinocloa crus-galli, respectively.

Example 33, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 75% and 60% herbicidal activity against Alopercurus myosuroides and Echinocloa crus-galli, respectively.

Example 35, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 36, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% and 75% herbicidal activity against Amaranthus retroflexus and Echinocloa crus-galli, respectively.

Example 39, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90%, 80%, 100% and 90% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 42, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% and 80% herbicidal activity against Amaranthus retroflexus and Abutilon theophrasti, respectively.

Example 43, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Echinocloa crus-galli.

Example 44, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 70% and 70% herbicidal activity against Setaria faberi and Abutilon theophrasti, respectively.

Example 45, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80%, 70% and 80% herbicidal activity against Alopercurus myosuroides, Setaria faberi and Echinocloa crus-galli, respectively.

Example 47, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 100% and 80% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Echinocloa crus-galli, respectively.

Example 52, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90% and 85% herbicidal activity against Echinocloa crus-galli and Setaria faberi.

Example 54, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90% and 100% herbicidal activity against Alopercurus myosuroides and Echinocloa crus-galli.

Example 56, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% and 95% herbicidal activity against Lolium multiflorum and Echinocloa crus-galli.

Example 58, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 90% and 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 60, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 100%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

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Example 61, used for pre-emergence treatment at an application rate of 250 g/ha, showed

80%, 100% and 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 65, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 95% and 95% herbicidal activity against Alopercurus myosuroides and Echinocloa crus-galli, respectively.

Example 69, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crusgalli and Setaria faberi.

Example 70, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Echinocloa crus-galli.

Example 72, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 73, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 70% and 75% herbicidal activity against Amaranthus retroflexus and Echinocloa crus-galli, respectively.

Example 74, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80% and 85% herbicidal activity against Amaranthus retroflexus and Echinocloa crus-galli, respectively.

Example 77, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80%, 100% and 100% herbicidal activity against Abutilon theophrasti, Setaria faberi and Echinocloa crusgalli, respectively.

Case 78, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 100% and 75% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 83, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi.

Case 85, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 70%, 70% and 90% herbicidal activity against Setaria faberi, Alopercurus myosuroides and Abutilon theophrasti, respectively.

Example 91, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crusgalli and Setaria faberi.

Case 94, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% and 70% herbicidal activity against Alopercurus myosuroides and Amaranthus retroflexus, respectively.

Example 96, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80%, 100%, 100% and 95% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively. Example 97, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 98, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80%, 90%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crusgalli and Setaria faberi, respectively. Example 99, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 100%, 90% and 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively. Example 100, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 100% and 80% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Abutilon theophrasti, respectively.

Example 102, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 100% and 85% herbicidal activity against Setaria faberi, Echinocloa crus-galli and Abutilon theophrasti, respectively.

Example 107, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 75%, 75%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively. Example 108, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 110, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90% and 80% herbicidal activity against Echinocloa crus-galli and Setaria faberi, respectively.

Example 111, used as a post-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti and Amaranthus retroflexus.

Example 111, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80% and 85% herbicidal activity against Apera spica-venti and Echinocloa crus-galli, respectively.

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Example 112 used for post-emergence treatment at an application rate of 250 g/ha showed

100% herbicidal activity against Abutilon theophrasti and Amaranthus retro flexus.

Example 112, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80% herbicidal activity against Apera spica-venti and Echinocloa crus-galli. Example 114, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90% herbicidal activity against Echinocloa crus-galli and Setaria faberi. Example 116, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 117, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 120, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 75%, 100% and 90% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 121 used for post-emergence treatment at an application rate of 250 g/ha showed 100% herbicidal activity against Abutilon theophrasti and Amaranthus retroflexus.

Example 121, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80% herbicidal activity against Amaranthus retroflexus. Example 125, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85% and 100% herbicidal activity against Apera spica-venti and Echinocloa crus-galli, respectively.

Example 128, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 90% and 90% herbicidal activity against Amaranthus retroflexus, Setaria faberi and Abutilon theophrasti, respectively.

Example 129, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 130, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Setaria faberi and Echinocloa crus-galli.

Example 131, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90%, 85% and 90% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Setaria faberi, respectively.

Example 132, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90%, 90% and 100% herbicidal activity against Amaranthus retroflexus, Setaria faberi and Echinocloa crusgalli, respectively.

Example 134, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 95%, 90% and 90% herbicidal activity against Apera spica-venti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 135, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Setaria faberi and Echinocloa crus-galli.

Example 136, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80%, 85% and 80% herbicidal activity against Apera spica-venti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 139, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 140, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98% and 100% herbicidal activity against Echinocloa crus-galli and Setaria faberi, respectively.

Example 141, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 100% and 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 142, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 143, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90% and 100% herbicidal activity against Alopercurus myosuroides and Amaranthus retroflexus, respectively.

Example 148, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 149, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 90% and 75% herbicidal activity against Alopercurus myosuroides, Setaria faberi and Echinocloa crus-galli, respectively.

Example 152, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% and 90% herbicidal activity against Amaranthus retroflexus and Setaria faberi, respectively.

Example 154, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

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Example 160, used for pre-emergence treatment at an application rate of 250 g/ha, showed

85% and 75% herbicidal activity against Alopercurus myosuroides and Setaria faberi, respectively.

Example 161, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Echinocloa crus-galli and Setaria faberi. Example 163, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi.

Example 164, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi.

Example 165, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crusgalli.

Example 167, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Setaria faberi.

Example 169, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80% and 85% herbicidal activity against Amaranthus retroflexus and Setaria faberi, respectively.

Example 170, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90%, 100% and 90% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 171, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 85% and 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 172, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi.

Example 173, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Echinocloa crus-galli.

Example 174, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi.

Example 175, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 100% and 95% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 176, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 100% and 80% herbicidal activity against Echinocloa crus-galli and Setaria faberi, Amaranthus retroflexus, respectively.

Example 177, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 100% and 95% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 178, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 180, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 181, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 182, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 183, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi.

Example 184, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 95% and 98% herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus and Echinocloa crus-galli, respectively.

Case 185, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 186, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85% and 98% herbicidal activity against Alopercurus myosuroides, and Echinocloa crus-galli, respectively.

Example 187, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

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Example 188, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crus-galli.

Example 189, used for pre-emergence treatment at an application rate of 250 g/ha, showed

98%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 191, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 95%, 100% and 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 192, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Echinocloa crus-galli and Setaria faberi.

Example 193, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80%, 95% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 194, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% and 70% herbicidal activity against Echinocloa crus-galli and Setaria faberi, respectively.

Example 196, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 100% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 198, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 100% and 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 199, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crusgalli.

Example 200, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi.

Example 201, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi.

Example 202, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80%, 80% and 85% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 203, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi.

Example 204, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi.

Example 205, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi.

Example 206, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi.

Example 207, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90%, 100% and 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 208, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90% and 80% herbicidal activity against Abutilon theophrasti and Amaranthus retroflexus, respectively.

Example 209, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 210, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 211, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 212, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Example 213, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi.

Case 214, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 98% and 90% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Setaria faberi, respectively.

Case 215, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 98% and 98% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

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Example 216, used for pre-emergence treatment at an application rate of 250 g/ha, showed

100%, 98% and 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Setaria faberi, respectively.

Example 217, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 100% and 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 218, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 95%, 85% and 100% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 219, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 85% and 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 220, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 95% and 90% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 222, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 100% and 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 223, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 95% and 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Example 224, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 90% and 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively.

Case 226, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90%, 100% and 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crus-galli, respectively.

Example 227, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90%, 75% and 85% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively.

Example 228, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 100% and 90% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crus-galli, respectively.

Example 229, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crusgalli.

Example 230, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 95%, 95% and 95% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 231, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 98% and 98% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crus-galli, respectively.

Example 232, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi.

Example 233, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 75%, 80% and 95% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crus-galli, respectively.

Example 234, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 90% and 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crus-galli, respectively.

Case 235, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 90% and 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 236, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 95% and 100% herbicidal activity against Abutilon theophrasti, Alopercurus myosuroides and Echinocloa crus-galli, respectively.

Example 237, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 95%, 100% and 95% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

Example 238, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 80%, 98% and 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively.

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Claims (8)

Example 240, used for pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 90% and 95% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively. Example 241, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 85% and 85% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi, respectively. Example 243, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 85% and 85% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively. Example 244, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 85%, 75% and 75% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Setaria faberi, respectively. Example 246, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, and Echinocloa crus-galli. Example 247, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi. Example 248, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, and Echinocloa crus-galli. Example 249, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi. Example 250, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, and Echinocloa crus-galli. Case 251, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 98%, 95% and 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi, respectively. Case 252, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100%, 95% and 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Setaria faberi, respectively. Example 254, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi. Example 255, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 90%, 95% and 90% herbicidal activity against Alopercurus myosuroides, Echinocloa crus-galli and Setaria faberi, respectively. Example 256, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria faberi. Example 257, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Abutilon theophrasti, Echinocloa crus-galli and Setaria faberi. Example 259, used as a pre-emergence treatment at an application rate of 250 g/ha, showed 100% herbicidal activity against Amaranthus retroflexus and Setaria faberi. CLAIM 1. Diaminotriazine compound of formula (I) where q represents 0, 1, 2 or 3; Q represents O; R ^a is selected from the group consisting of halogen, CN, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy and C 1 -C 4 -haloalkoxy, where parts of the radicals are unsubstituted, partially or completely halogenated; R ^b is selected from the group consisting of halogen, CN, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy and C 1 -C 4 -haloalkoxy, where parts of the radicals are unsubstituted, partially or completely halogenated; for q = 2 or 3 it is possible that R ^b are the same or different; R ¹ is selected from the group consisting of H, C ₁ -C ₆ -alkyl; - 100 044989 R ² is selected from the group consisting of H, halogen, OH, CN, Ci-Ce-alkyl, (C1-Cb-alkoxy)-C1-Cbalkyl, C ₃ -Cb-cycloalkyl, (C ₃ -Cb-cycloalkyl)- C1-C4-alkyl, Ci-Ce-alkoxy, _C2 -Cb-alkenyloxy, _C2 -Sealkynyloxy, _C3 - _C6 -cycloalkoxy, ( _C3 - _C6 -cycloalkyl)-C1- _C4 -alkoxy, where the aliphatic and cycloaliphatic parts of the radicals are unsubstituted, partially or completely halogenated; R ³ is selected from the group consisting of H, halogen, CN, C1-C ₆ -alkyl, C1-C ₆ -haloalkyl, Ci-C ₆ alkoxy and C1-C ₆ -haloalkoxy; R ⁴ is selected from the group consisting of halogen, CN, C 1 -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₃ -C ₆ -alkynyl, C ₃ -C ₆ -cycloalkyl, (C ₃ -C ₆ - cycloalkyl)-C1-C ₄ -alkyl, C ₃ -C ₆ -cycloalkenyl and C1-C ₆ -alkoxy-C1-C ₆ alkyl, where the aliphatic and cycloaliphatic parts of the radicals are unsubstituted, partially or completely halogenated; or R ³ and R ⁴ together with the carbon atom to which they are attached form a substituent selected from the group consisting of carbonyl, C3-Ce-cycloalkyl, C3-Cb-cycloalkenyl, and the substituent >C=CR ^x R ^y , where R ^x and R ^y represent hydrogen, C1-C4 alkyl, C1-C ₄ haloalkyl, C ₃ -Cb-cycloalkyl or CR ^x R ^y forms a 3-6 membered cycloalkyl; R ⁵ is selected from the group consisting of H, C1-C ₆ -alkyl; R ⁶ is phenyl which is unsubstituted or carries 1, 2, 3, 4 or 5 R ^6A radicals which are selected from the group consisting of halogen, OH, CN, amino, NO ₂ , C 1 -C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -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, (Ci-C ₆ alkoxy)-C1-C ₆ -alkoxy, (C1-C ₆ -alkoxy)-C ₂ -C ₆ -alkenyl, (C1-C ₆ -alkoxy)-C ₂ -C ₆ -alkynyl , Ci-C ₆ alkylthio, (C1-C ₆ -alkyl)sulfinyl, (C1-C ₆ -alkyl)sulfonyl, (C1-C ₆ -alkyl)amino, di(C1-C ₆ -alkyl)amino, (C1 -Cb-alkyl)carbonyl, (C1-Cb-alkoxy)carbonyl, (C1-Cb-alkyl)carbonyloxy, C ₃ -Ce-cycloalkyl, C ₃ -Cb-cycloalkoxy, (C ₃ -Cb-cycloalkyl)-C1- C ₄ -alkyl, (C ₃ -Cb-cycloalkyl)-C1-C ₄ -alkoxy, where the aliphatic and cycloaliphatic parts of the radicals are unsubstituted, partially or completely halogenated and where the cycloaliphatic parts of the radicals can carry 1, 2, 3, 4, 5 or 6 methyl groups, it is possible that R ^6A are the same or different; R ⁷ and R ⁷ are independently selected from the group consisting of hydrogen, halogen, C1- _C4 alkyl, _C2 - _C6 alkenyl, _C2 - _C6 alkynyl, C1- _C6 alkoxy, C1- _C6 - haloalkoxy, C ₃ -C ₆ -cycloalkyl; or agriculturally acceptable salts thereof. 2. A compound according to claim 1, where R ^a is selected from fluorine or chlorine. 3. A compound according to any of the preceding claims, wherein R ^b represents fluorine, chlorine, bromine or methyl. 4. A compound according to any of the preceding claims, wherein R ¹ is H. 5. A compound according to any of the preceding paragraphs, wherein R ² is selected from the group consisting of hydrogen, fluorine, C1- _C4 alkyl and C1- _C4 alkoxy; R ³ is selected from the group consisting of hydrogen, fluorine, C1-C ₄ alkyl, C1-C ₄ haloalkyl, Ci-C ₄ alkoxy and Ci-Cb-haloalkoxy; R ⁴ is selected from the group consisting of Ci-Ce-alkyl, Ci-Cb-haloalkyl, C ₂ -Ce-alkenyl, C ₃ -Sealkynyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkenyl and C1- C ₆ -alkoxy-C1-C ₆ -alkyl; or R ³ and R ⁴ together with the carbon atom to which they are attached form a substituent which is selected from the group consisting of C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkenyl. 6. A compound according to any of the preceding claims, wherein R ⁵ is H. 7. A compound according to any of the preceding claims, wherein R ^6A , if present, is selected from the group consisting of halogen, CN, C1- _C4 alkyl, C1- _C4 haloalkyl, C1- _C4 alkoxy, Ci-C ₄ haloalkoxy and C ₃ -Ce-cycloalkyl. 8. A herbicidal composition containing a herbicidal active amount of at least one compound according to any one of claims 1 to 7, and at least one inert liquid and/or solid carrier, and at least one surfactant. Eurasian Patent Organization, EAPO Russia, 109012, Moscow, Maly Cherkassky lane, 2 - 101 -