Diaminotriazine compound

Abstract

The present invention relates to diamino triazine compounds and their use as herbicides. The present invention also relates to agrochemical compositions for crop protection and a method for controlling the growth of unwanted plants.

Description

[0001] The present invention relates to diamino triazine compounds and their use as herbicides. The present invention also relates to agrochemical compositions for crop protection and a method for controlling unwanted plant growth.

[0002] Diamino triazines and their use as herbicides are known, for example, from WO 2015 / 155272 and WO 2015 / 162166.

[0003] However, there is still room for improvement, for example, with respect to the activity, activity spectrum and compatibility with useful plants of known herbicidal compounds.

[0004] Therefore, the object of the present invention is to provide compounds having improved herbicidal action, in particular good herbicidal activity at low application rates. In addition, the herbicides should be fully compatible with commercially exploited crop plants.

[0005] These and other objects are achieved by the diamino triazine compounds of formula (I) and their agriculturally usable salts as defined below.

[0006] Accordingly, the present invention relates to diamino triazine compounds of formula (I):

[0007]

[0008] wherein

[0009] q is 0, 1, 2 or 3,

[0010] Q is O, S(O) m , CR q1 R q2 , NR q3 , C(O), S(O) m NR q3 or,

[0011] wherein

[0012] m is 0, 1 or 2;

[0013] R q1 , R q2 are hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl;

[0014] R q3 is H, CN, C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkyl)-carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkyl)sulfonyl, wherein the aliphatic moiety of said groups is unsubstituted, partially or fully halogenated;

[0015] R aSelected from hydrogen, halogen, OH, CN, amino, NO2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C1-C6 alkylthio, (C1-C6 alkyl)sulfinyl, (C1-C6 alkyl)sulfonyl, (C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkyl)-carbonyl, (C1-C6 alkoxy)-carbonyl, (C1-C6 alkyl)-carbonyloxy, wherein the aliphatic and cycloaliphatic moieties of said groups are unsubstituted, partially or completely halogenated;

[0016] R b Selected from halogen, OH, CN, amino, NO2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkoxy, (C1-C6 alkoxy)-C2-C6 alkenyl, (C1-C6 alkoxy)-C2-C6 alkynyl, C1-C6 alkylthio, (C1-C6 alkyl)sulfinyl, (C1-C6 alkyl)sulfonyl, (C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkyl)-carbonyl, (C1-C6 alkoxy)-carbonyl, (C1-C6 alkyl)-carbonyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, (C3-C6 cycloalkyl)-C1-C4 alkyl, (C3-C6 cycloalkyl)-C1-C4 alkoxy, wherein the aliphatic and cycloaliphatic moieties of said groups are unsubstituted, partially or completely halogenated and wherein the cycloaliphatic moieties of the latter-mentioned 4 groups may bear 1, 2, 3, 4, 5 or 6 methyl groups,

[0017] For q = 2 or 3, where it is possible that R b are the same or different;

[0018] R 1 Selected from H, OH, S(O)2NH2, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C3-C6 cycloalkyl)-C1-C4 alkyl, C1-C6 alkoxy, (C1-C6 alkoxy)-C1-C6 alkyl, (C3-C6 cycloalkyl)carbonyl, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkyl)sulfonyl, (C1-C6 alkylamino)carbonyl, di(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkylamino)sulfonyl, di(C1-C6 alkyl)aminosulfonyl and (C1-C6 alkoxy)sulfonyl, wherein the aliphatic and cycloaliphatic moieties of said groups are unsubstituted, partially or completely halogenated,

[0019] phenyl, phenyl-C1-C6 alkyl, phenylsulfonyl, phenylaminosulfonyl, phenylaminocarbonyl, phenyl(C1-C6 alkyl)aminocarbonyl, phenylcarbonyl and phenoxycarbonyl,

[0020] wherein the phenyl in the latter-mentioned 8 groups is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0021] R 2 is selected from H, halogen, OH, CN, C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkyl, C3-C6 cycloalkyl, (C3-C6 cycloalkyl)-C1-C4 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkoxy, (C3-C6 cycloalkyl)-C1-C4 alkoxy, wherein the aliphatic and cycloaliphatic moieties of the said groups are unsubstituted, partially or completely halogenated;

[0022] R 3 is selected from H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0023] R 4 is selected from halogen, CN, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, (C3-C6 cycloalkyl)-C1-C4 alkyl, C3-C6 cycloalkenyl and C1-C6 alkoxy-C1-C6 alkyl, wherein the aliphatic and cycloaliphatic moieties of the said groups are unsubstituted, partially or completely halogenated;

[0024] R 3 and R 4 together with the carbon atom to which they are attached form a structural moiety selected from carbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, 3-6 membered saturated or partially unsaturated heterocyclic group, and the structural moiety >C=CR x R y wherein R x and R y are hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl or CR x R y forms a 3-6 membered cycloalkyl;

[0025] R 5selected from H, OH, S(O)2NH2, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C3-C6 cycloalkyl)-C1-C4 alkyl, (C3-C6 cycloalkyl)carbonyl, C1-C6 alkoxy, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkyl)sulfonyl, (C1-C6 alkylamino)carbonyl, bis(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkylamino)sulfonyl, bis(C1-C6 alkyl)aminosulfonyl and (C1-C6 alkoxy)sulfonyl, wherein the aliphatic and cycloaliphatic moieties of said groups are unsubstituted, partially or fully halogenated,

[0026] phenyl, phenylsulfonyl, phenylaminosulfonyl, phenylaminocarbonyl, phenyl(C1-C6 alkyl)aminocarbonyl, phenyl-C1-C6 alkyl, phenoxy, phenylcarbonyl and phenoxycarbonyl,

[0027] wherein the phenyl in the latter-mentioned 9 groups is unsubstituted or substituted with 1, 2, 3, 4 or 5 identical or different substituents selected from halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0028] R 6 is phenyl or a 5- or 6-membered heteroaryl which is unsubstituted or bears 1, 2, 3, 4 or 5 groups R 6A which are selected from halogen, OH, CN, amino, NO2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkoxy, (C1-C6 alkoxy)-C2-C6 alkenyl, (C1-C6 alkoxy)-C2-C6 alkynyl, C1-C6 alkylthio, (C1-C6 alkyl)sulfinyl, (C1-C6 alkyl)sulfonyl, (C1-C6 alkyl)amino, bis(C1-C6 alkyl)amino, (C1-C6 alkyl)-carbonyl, (C1-C6 alkoxy)-carbonyl, (C1-C6 alkyl)-carbonyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, (C3-C6 cycloalkyl)-C1-C4 alkyl, (C3-C6 cycloalkyl)-C1-C4 alkoxy, wherein the aliphatic and cycloaliphatic moieties of said groups are unsubstituted, partially or fully halogenated and wherein the cycloaliphatic moiety of said groups may bear 1, 2, 3, 4, 5 or 6 methyl groups,

[0029] wherein it is possible that R 6A are identical or different;

[0030] R 7and R 7′ are independently selected from hydrogen, halogen, OH, CN, NO2, SH, NH2, NH(C1-C4 alkyl), N(C1-C4 alkyl)2, NH-SO2-C1-C4 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl; and

[0031] wherein R 7 and R 7′ the aliphatic structural moieties of which are not further substituted or carry 1, 2, 3 or at most the maximum possible number of identical or different groups R 7a or R 7′a , which are independently of one another selected from:

[0032] R 7a , R 7′a halogen, OH, CN, C1-C6 alkoxy, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 haloalkoxy and C1-C6 alkylthio;

[0033] wherein R 7 and R 7 the cycloalkyl structural moieties of which are not further substituted or carry 1, 2, 3, 4, 5 or at most the maximum number of identical or different groups R 7b or R 7′b , which are independently of one another selected from:

[0034] R 7b , R 7′b halogen, OH, CN, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 haloalkoxy and C1-C6 alkylthio;

[0035] including their agrochemically acceptable salts or derivatives.

[0036] The invention also relates to an agrochemical composition comprising at least one diamino-triazine compound of formula (I) and auxiliaries customarily used in the preparation of crop protection agents.

[0037] The invention also relates to the use of a diamino-triazine compound of formula (I) as a herbicide, i.e. for controlling the growth of unwanted and / or harmful plants or vegetation.

[0038] Furthermore, the invention provides a method for controlling unwanted plants. The method comprises applying an herbicidally effective amount of at least one diamino-triazine compound of formula (I) to the unwanted plants or their growth, their seeds and / or their growth sites. The application can be carried out before, during and / or after emergence of the unwanted plants, preferably during and / or after emergence.

[0039] Furthermore, the present invention relates to a method for preparing a diaminotriazine compound of formula (I) and intermediates.

[0040] Other embodiments of the present invention are apparent from the claims, the description and the examples. It should be understood that the features mentioned above and still to be described below of the subject matter of the present invention can be used not only in the combinations given in each particular case but also in other combinations without departing from the scope of the present invention.

[0041] As used herein, the terms "control" and "eradication" are synonyms.

[0042] As used herein, the terms "undesired plant growth", "unwanted plant growth", "unwanted plants" and "harmful plants" are synonyms.

[0043] With respect to substituents, the term "one or more substituents" means that the number of substituents is, for example, 1 - 10, especially 1, 2, 3, 4, 5, 6, 7 or 8.

[0044] If the diaminotriazine compounds of formula (I) described herein are capable of forming geometric isomers, such as E / Z isomers, then the present invention relates to both the pure isomers and their mixtures. Similarly, the present invention relates to the use of the pure isomers and their mixtures, and to compositions containing the pure isomers or their mixtures.

[0045] If the diaminotriazine compounds of formula (I) described herein have one or more chiral centers and thus exist as enantiomers or diastereomers, then the present invention relates to both the pure enantiomers or diastereomers and their mixtures. Similarly, the present invention relates to the use of the pure enantiomers or diastereomers and their mixtures, and to compositions containing the pure enantiomers or diastereomers and their mixtures.

[0046] If the diaminotriazine compounds of formula (I) described herein have ionizable functional groups, they can also be used in their agrochemically acceptable salt forms. Suitable are generally those salts of cations and those acid addition salts of acids whose cations and anions respectively have no adverse effect on the activity of the active compound.

[0047] Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium ions, ions of alkaline earth metals, preferably calcium and magnesium ions, and ions of transition metals, preferably manganese, copper, zinc and iron ions, and also ammonium and substituted ammonium in which 1 to 4 hydrogen atoms are replaced by C1-C4 alkyl, hydroxy-C1-C4 alkyl, C1-C4 alkoxy-C1-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 (alkanolamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diethanolamine salt), bis(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (triethanolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), and also ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium such as trimethylsulfonium, and sulfoxonium ions, preferably tri(C1-C4 alkyl)sulfoxonium, and finally salts of polyamines such as N,N-bis(3-aminopropyl)methylamine and diethylenetriamine.

[0048] The anions of the useful acid addition salts are mainly chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also anions of C1-C4 alkanoic acids, preferably formate, acetate, propionate and butyrate.

[0049] Other embodiments of the invention are apparent from the claims, the description and the examples. It should be understood that the features mentioned above and still to be described below of the subject matter of the invention can be used not only in the combinations given in each specific case, but also in other combinations without departing from the scope of the invention.

[0050] In variables such as Q, q, R q1 、R q2 、R a 、R b 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 7′The organic structural moieties mentioned in the definition are collective terms for the individual listing of each group member, like the term halogen. The term halogen means fluorine, chlorine, bromine or iodine in each case. All hydrocarbon chains, i.e., all alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, (alkyl)amino, bis(alkyl)amino, alkoxyalkyl, alkoxyalkoxy, (alkyl)carbonyl, (alkoxy)carbonyl chains, can be straight-chain or branched, and the prefix C n -C m represents in each case the possible number of carbon atoms in the group. The same applies to complex groups, such as cycloalkylalkyl and phenylalkyl.

[0051] Examples of such meanings are:

[0052] -C1-C4 alkyl and also C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfonyl, (C1-C4 alkyl)carbonyl, (C1-C4 alkyl)carbonyl, (C1-C4 alkoxy)carbonyl, (C1-C4 alkyl)carbonyloxy, C1-C4 alkoxy-C1-C4 alkyl, C3-C6 cycloalkyl-C1-C4 alkyl, (C1-C4 alkylamino)carbonyl, bis(C1-C4 alkyl)aminocarbonyl, (C1-C4 alkylamino)sulfonyl, bis(C1-C4 alkyl)aminosulfonyl or phenyl-C1-C4 alkyl C1-C4 alkyl structural moieties: for example, CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2H5, CH2-CH(CH3)2 and C(CH3)3;

[0053] -C1-C6 alkyl and also C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, (C1-C6 alkyl)carbonyl, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkyl)carbonyloxy, C1-C6 alkoxy-C1-C6 alkyl, C3-C6 cycloalkyl-C1-C6 alkyl, phenyl(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkylamino)carbonyl, di(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkylamino)sulfonyl, di(C1-C6 alkyl)aminosulfonyl or phenyl-C1-C6 alkyl C1-C6 alkyl structural moiety: C1-C4 alkyl as described above and also for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl;

[0054] -C2-C6 alkenyl and also the C2-C6 alkenyl structural moiety of (C1-C6 alkoxy)-C2-C6 alkenyl: a linear or branched alkenyl-unsaturated hydrocarbon group having 2-6 carbon atoms and a C═C double bond at any position, such as vinyl, 1-propenyl, 2-propenyl, 1-methyl-vinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

[0055] -C2-C6 alkynyl and (C1-C6 alkoxy)-C2-C6 alkynyl C2-C6 alkynyl structural moieties: linear or branched unsaturated hydrocarbon groups having 2-6 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, etc.;

[0056] -C1-C4 haloalkyl: the above-mentioned C1-C4 alkyl partially or completely substituted by fluorine, chlorine, bromine and / or iodine, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-fluoromethyl-2-fluoroethyl, 1-chloromethyl-2-chloroethyl, 1-bromomethyl-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1,1,2,2-tetrafluoroethyl and 1-trifluoromethyl-1,2,2,2-tetrafluoroethyl;

[0057] -C1-C6 haloalkyl: the above-mentioned C1-C4 haloalkyl and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;

[0058] -C3-C6 cycloalkyl: monocyclic saturated hydrocarbons having 3-6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

[0059] -C1-C4 alkoxy: for example, methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

[0060] -C1-C6 alkoxy groups, as well as (C1-C6 alkoxy)carbonyl, (C1-C6 alkoxy)sulfonyl, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkoxy, (C1-C6 alkoxy)-C2-C6 alkenyl, and (C1-C6 alkoxy)-C2-C6 alkynyl C1-C6 alkoxy structural moieties: C1-C4 alkoxy groups as described above, as well as, for example, pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxybutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methyl-propoxy, and 1-ethyl-2-methylpropoxy;

[0061] -C1-C4 haloalkoxy groups: C1-C4 alkoxy groups as described above that are partially or fully substituted with fluorine, chlorine, bromine, and / or iodine, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichloro-fluoromethoxy, chloro-difluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 4-fluorobutoxy, nonafluorobutoxy, 1,1,2,2,-tetrafluoroethoxy, and 1-trifluoromethyl-1,2,2,2-tetrafluoroethoxy;

[0062] -C1-C6 haloalkoxy groups: C1-C4 alkoxy groups as described above: C1-C4 haloalkoxy groups as described above, as well as, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, and dodecafluorohexyl;

[0063] -C2-C6 alkenyloxy: An alkenyl group as defined above bonded via an oxygen atom, such as vinyloxy (ethenyloxy), 1-propenyloxy, 2-propenyloxy (allyloxy), 1-butenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-2-propenyloxy, etc.;

[0064] -C2-C6 alkynyloxy: An alkynyl group as defined above bonded via an oxygen atom, such as ethynyloxy, 1-propynyloxy, 2-propynyloxy (propargyloxy), 1-butynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, etc.;

[0065] -C1-C4 alkylthio: For example, methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, and 1,1-dimethylethylthio;

[0066] -C1-C6 alkylthio: The C1-C4 alkylthio as described above and also, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio;

[0067] -C1-C6 alkylsulfinyl (C1-C6 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, 1,1-dimethylpropylsulfinyl, 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;

[0068] -C1-C6 alkylsulfonyl (C1-C6 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, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

[0069] -(C1-C4 alkyl)amino and also (C1-C4 alkylamino)carbonyl or (C1-C4 alkylamino)sulfonyl (C1-C4 alkylamino) structural moieties: for example, methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino or 1,1-dimethylethylamino;

[0070] -(C1-C6 alkyl)amino and also (C1-C6 alkylamino)carbonyl, phenyl(C1-C6 alkyl)aminocarbonyl or (C1-C6 alkylamino)sulfonyl (C1-C6 alkylamino) structural moieties: (C1-C4 alkyl)amino as described above and also, for example, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 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, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;

[0071] -Bis(C1-C4 alkyl)amino and also bis(C1-C4 alkylamino)structural moieties having bis(C1-C4 alkylaminocarbonyl) or bis(C1-C4 alkylaminosulfonyl): for example, N,N-dimethylamino, N,N-diethylamino, N,N-di(1-methylethyl)amino, N,N-dipropylamino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-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, N-butyl-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-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;

[0072] -bis(C1-C6 alkyl)amino and a bis(C1-C6 alkylamino) structural moiety also having bis(C1-C6 alkylaminocarbonyl) or bis(C1-C6 alkylaminosulfonyl): bis(C1-C4 alkyl)amino as described above and also, for example, N-methyl-N-pentylamino, N-methyl-N-(1-methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-methyl-N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1-ethylpropyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1,1-dimethylpropyl)amino, N-methyl-N-(1,2-dimethylpropyl)amino, N-methyl-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)amino, N-methyl-N-(1-ethylbutyl)amino, N-methyl-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-ethyl-N-pentylamino, N-ethyl-N-(1-methylbutyl)amino, N-ethyl-N-(2-methylbutyl)amino, N-ethyl-N-(3-methylbutyl)amino, N-ethyl-N-(2,2-dimethylpropyl)amino, N-ethyl-N-(1-ethylpropyl)amino, N-ethyl-N-hexylamino, N-ethyl-N-(1,1-dimethylpropyl)amino, N-ethyl-N-(1,2-dimethylpropyl)amino, N-ethyl-N-(1-methylpentyl)amino, N-ethyl-N-(2-methylpentyl)amino, N-ethyl-N-(3-methylpentyl)amino, N-ethyl-N-(4-methylpentyl)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, N-ethyl-N-(3,3-dimethylbutyl)amino, N-ethyl-N-(1-ethylbutyl)amino, N-ethyl-N-(2-ethylbutyl)amino, N-ethyl-N-(1,1,2-trimethylpropyl)amino, N-ethyl-N-(1,2,2-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;,

[0073] -C3-C6 cycloalkyl and also structural moieties of C3-C6 cycloalkyl having (C3-C6 cycloalkyl)carbonyl, (C3-C6 cycloalkyl)-C1-C6 alkyl, (C3-C6 cycloalkyl)carbonyl and (C3-C6 cycloalkyl)-C1-C6 alkoxy: cycloaliphatic groups having 3-6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

[0074] -C3-C6 cycloalkoxy: cycloaliphatic groups having 3-6 carbon atoms and bonded via an oxygen atom, such as cyclopropoxy, cyclobutoxy, cyclopentyloxy and cyclohexyloxy;

[0075] -(C3-C6 cycloalkyl)-C1-C6 alkyl: C1-C6 alkyl as defined above, especially C1-C4 alkyl such as methyl or ethyl, wherein 1 hydrogen atom is replaced by C3-C6 cycloalkyl as defined above, examples include cyclopropylmethyl (CH2-cyclopropyl), cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropylethyl (CH(CH3)-cyclopropyl), 1-cyclobutylethyl, 1-cyclopentylethyl, 1-cyclohexylethyl, 2-cyclopropylethyl (CH2CH2-cyclopropyl), 2-cyclobutylethyl, 2-cyclopentylethyl or 2-cyclohexylethyl;

[0076] -(C3-C6 cycloalkyl)-C1-C6 alkoxy: C1-C6 alkoxy as defined above, especially C1-C4 alkoxy such as methoxy or ethoxy, wherein 1 hydrogen atom is replaced by C3-C6 cycloalkyl as defined above, examples include cyclopropylmethoxy (OCH2-cyclopropyl), cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, 1-cyclopropylethoxy (OCH(CH3)-cyclopropyl), 1-cyclobutylethoxy, 1-cyclopentylethoxy, 1-cyclohexylethoxy, 2-cyclopropylethoxy (OCH2CH2-cyclopropyl), 2-cyclobutylethoxy, 2-cyclopentylethoxy or 2-cyclohexylethoxy;

[0077] -(C1-C6 alkoxy)-C1-C6 alkyl: A C1-C6 alkyl as defined above, especially a C1-C4 alkyl such as methyl, ethyl or isopropyl, wherein one hydrogen atom is replaced by a C1-C6 alkoxy as defined above. Examples include methoxymethyl, ethoxymethyl, n-propoxymethyl, butoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-n-propoxyethyl, 1-butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-n-propoxyethyl, 2-butoxyethyl, 2-methoxypropyl, 2-ethoxypropyl, 2-n-propoxypropyl, 2-butoxypropyl;

[0078] -(C1-C6 alkoxy)-C1-C6 alkoxy: A C1-C6 alkoxy as defined above, especially a C1-C4 alkoxy such as methoxy or ethoxy, wherein one hydrogen atom is replaced by a C1-C6 alkoxy as defined above. Examples include methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, butoxymethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-n-propoxyethoxy and 2-butoxyethoxy;

[0079] -(C1-C6 alkoxy)-C2-C6 alkenyl: A C2-C6 alkenyl as defined above, especially a C2-C4 alkenyl such as vinyl, propenyl, 1-butenyl or 2-butenyl, wherein one hydrogen atom is replaced by a C1-C6 alkoxy as defined above;

[0080] -(C1-C6 alkoxy)-C2-C6 alkynyl: A C2-C6 alkynyl as defined above, especially a C2-C4 alkynyl such as ethynyl, propynyl or 2-butynyl, wherein one hydrogen atom is replaced by a C1-C6 alkoxy as defined above;

[0081] -(C1-C6 alkyl)carbonyl: A C1-C6 alkyl as described above bonded to the remainder of the molecule through a carbonyl;

[0082] -(C1-C6 alkoxy)carbonyl: A C1-C6 alkoxy as described above bonded to the remainder of the molecule through a carbonyl;

[0083] -(C1-C6 alkylamino)carbonyl: A (C1-C6 alkyl)amino bonded to the remainder of the molecule through a carbonyl;

[0084] -(C1-C6 alkylamino)sulfonyl: A (C1-C6 alkyl)amino as described above bonded to the remainder of the molecule through a sulfonyl;

[0085] -di(C1-C6 alkylamino)carbonyl: A di(C1-C6 alkyl)amino as described above bonded to the remainder of the molecule through a carbonyl;

[0086] -Di(C1-C6 alkylamino)sulfonyl: Di(C1-C6 alkyl)amino as described above bonded through the sulfonyl group to the remainder of the molecule;

[0087] -Phenyl-C1-C6 alkyl: A C1-C6 alkyl as defined above, especially a C1-C4 alkyl such as methyl or ethyl, where one hydrogen atom is replaced by a phenyl group, examples including benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 1-phenyl-1-methylethyl, etc.;

[0088] -3-6 membered heterocyclic group: A monocyclic saturated or partially unsaturated hydrocarbon as described above having 3-6 ring members, which contains 1 or 2 heteroatoms selected from O, S, and N in addition to carbon atoms;

[0089] For example, saturated heterocycles such as 2-oxiranyl, 2-oxetanyl, 3-oxetanyl, 2-aziridinyl, 3-thietanyl, 1-azetidinyl, 2-azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-is oxazolidinyl, 4-is oxazolidinyl, 5-is oxazolidinyl, 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-di alkyl-2-yl, 1,3-di alkyl-4-yl, 1,3-di alkyl-5-yl, 1,4-di alkyl-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-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, tetrahydro-1,3- oxazin-2-yl, tetrahydro-1,3- a 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl;

[0090] - Partially unsaturated heterocycles such as 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,4-dihydrofuran-2-yl, 2,4-dihydrofuran-3-yl, 2,3-dihydrothiophene-2-yl, 2,3-dihydrothiophene-3-yl, 2,4-dihydrothiophene-2-yl, 2,4-dihydrothiophene-3-yl, 4,5-dihydropyrrol-2-yl, 4,5-dihydropyrrol-3-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 4,5-dihydrois oxazol-3-yl, 2,5-dihydrois oxazol-3-yl, 2,3-dihydrois oxazol-3-yl, 4,5-dihydrois oxazol-4-yl, 2,5-dihydrois oxazol-4-yl, 2,3-dihydrois oxazol-4-yl, 4,5-dihydrois oxazol-5-yl, 2,5-dihydrois oxazol-5-yl, 2,3-dihydrois oxazol-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-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-3-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2,3-dihydro oxazol-3-yl, 2,3-dihydro oxazol-4-yl, 2,3-dihydro oxazol-5-yl, 3,4-dihydro oxazol-3-yl, 3,4-dihydro oxazol-4-yl, 3,4-dihydro oxazol-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, 3,4-dihydrothiazol-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-2H-pyran-3-yl, 3,4-dihydro-2H-pyran-4-yl, 3,4-dihydro-2H-pyran-6-yl, 5,6-dihydro-4H-1,3- azin-2-yl;

[0091] -5- and 6-membered heteroaryl groups containing 1, 2 or 3 heteroatoms selected from O, S and N:

[0092] -5- and 6-membered heteroaromatic groups containing, in addition to carbon atoms, 1, 2 or 3 heteroatoms selected from O, S and N as ring members, such as 1, 2 or 3 nitrogen atoms or 1 oxygen or sulfur atom and optionally 1 or 2 nitrogen atoms:

[0093] In particular:

[0094] -5-membered monocyclic heteroaryl groups containing 1 - 3 heteroatoms selected from O, S and N: such as 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, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, etc.;

[0095] -6-membered monocyclic heteroaryl groups containing 1 - 3 nitrogen atoms as ring members:

[0096] such as 2-pyridyl, 3-pyridyl, 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 1,3,5-triazinyl.

[0097] The preferred embodiments of the present invention described below must be understood to be preferred either independently of one another or in combination with one another. Certain groups of embodiments of the present invention relate to those diamino-triazines of formula (I) in which the variables Q, q, m, R q1 , R q2 , R q3 , R a , R b , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 7 independently of one another or in combination with one another have the following meanings:

[0098] Certain groups of embodiments relate to diamino-triazine compounds of formula (I) in which Q has the meaning defined above.

[0099] Q is in particular O, CR q1 R q2 , C(O) or S(O)2, where R q1 and R q2 are the same or different and are selected from hydrogen, halogen, C1-C4 alkyl and C1-C4 haloalkyl.

[0100] Particularly preferably, Q is O, CH2, C(O),

[0101] Most preferably, Q is O.

[0102] Other specific groups of embodiments relate to diamino-triazine compounds of formula (I) in which R a is as defined above.

[0103] In particular, R a is selected from halogen, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, where the aliphatic moieties of the above six groups are unsubstituted, partially or fully halogenated,

[0104] For q = 2 or 3, it is possible that R a are the same or different.

[0105] More particularly, R a is selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy.

[0106] even more particularly R a is selected from F, Cl, Br, CN.

[0107] Embodiments of other specific groups relate to diamino triazine compounds of the following formula (I), wherein R b is as defined above.

[0108] In particular R b is selected from halogen, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyl, wherein the aliphatic moieties of the above six groups are unsubstituted, partially or fully halogenated, and

[0109] for q = 2 or 3, where it is possible that R b are the same or different.

[0110] Even more particularly R b is selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C3-C6 cycloalkyl.

[0111] Even more particularly R b is selected from F, Cl, Br, CN, methyl, cyclopropyl, cyclobutyl.

[0112] Embodiments of other specific groups relate to diamino triazine compounds of the following formula (I), wherein: R 1 is H, OH, S(O)2NH2, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C3-C6 cycloalkyl)-C1-C4 alkyl, C1-C6 alkoxy, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkyl)-carbonyl, (C3-C6 cycloalkyl)-carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkyl)sulfonyl, (C1-C6 alkylamino)carbonyl, di(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkylamino)sulfonyl, di(C1-C6 alkyl)aminosulfonyl and (C1-C6 alkoxy)sulfonyl, wherein the aliphatic and cycloaliphatic moieties of the above fifteen groups are unsubstituted, partially or fully halogenated,

[0113] phenyl, phenyl-C1-C6 alkyl, phenylsulfonyl, phenylaminosulfonyl, phenylcarbonyl and phenoxycarbonyl, wherein the phenyl in the latter six groups is unsubstituted or substituted by one, two, three, four or five identical or different substituents selected from halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0114] preferably H, CN, C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkyl)carbonyl(C3-C6 cycloalkyl)-carbonyl or (C1-C6 alkyl)sulfonyl, wherein the aliphatic moiety of the above five groups is unsubstituted or completely halogenated,

[0115] phenyl and phenyl-C1-C6 alkyl,

[0116] wherein the phenyl in the latter two groups is unsubstituted or substituted by one, two, three, four or five identical or different substituents selected from halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0117] especially H, CN, C1-C6 alkyl, C1-C6 haloalkyl, (C1-C6 alkoxy)-C1-C6 alkyl, C1-C6 alkoxy, (C1-C6 alkyl)carbonyl, (C3-C6 cycloalkyl)-carbonyl, (C1-C6 haloalkyl)carbonyl, (C1-C6 alkyl)sulfonyl or (C1-C6 haloalkyl)sulfonyl;

[0118] more particularly H, CN, C1-C4 alkyl, (C1-C4 alkoxy)-C1-C4 alkyl, C1-C4 alkoxy, (C1-C4 alkyl)carbonyl, (C3-C6 cycloalkyl)-carbonyl or (C1-C4 alkyl)sulfonyl; even more particularly H, CN, CH3, CH2OCH3, OCH3, C(O)CH3, C(O)cyclopropyl or SO2CH3; especially hydrogen.

[0119] Other specific groups of embodiments relate to diamino triazine compounds of the following formula (I), wherein;

[0120] Also preferably diamino triazine compounds of the following formula (I), wherein

[0121] R 2is selected from H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, in particular selected from hydrogen, fluorine, C1-C4-alkyl, for example methyl, ethyl, n-propyl, 2-propyl, n-butyl, 2-butyl, isobutyl or tert-butyl, C1-C4-haloalkyl, for example difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl, C1-C4-alkoxy, for example methoxy or ethoxy, and C1-C4-haloalkoxy, for example difluoromethoxy or trifluoromethoxy.

[0122] Another specific group (1) of embodiments relates to diaminotriazine compounds of formula (I) wherein R 3 is selected from H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy, in particular selected from hydrogen, fluorine and C1-C4-alkyl, more in particular selected from hydrogen, fluorine and methyl, especially selected from fluorine and methyl.

[0123] In the embodiment of group (1), R 4 As defined above.

[0124] R 4 Selected from C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C1-C6 alkoxy and C1-C6 alkoxy-C1-C6 alkyl or selected from C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C1-C6 alkoxy and C1-C6 alkoxy-C1-C6 alkyl.

[0125] Another specific group (2) of embodiments relates to diaminotriazine compounds of formula (I) wherein R 3 and R 4 Together with the carbon atom to which it is attached, it forms a moiety selected from carbonyl, C3-C6 cycloalkane-1,1-diyl, idiomeric C3-C6 cycloalkenediyl, idiomeric 3-6 membered saturated or partially unsaturated idiomeric heterocyclic diyl, wherein the carbocyclic and heterocyclic rings are unsubstituted, partially or fully halogenated or carry 1-6 C1-C6 alkyl groups, and the moiety>C=CR x R y , where R x and R y is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl or CR x R y A 3-6 membered cycloalkyl group is formed.

[0126] In the embodiment of group (2), R3 and R 4 Together with the carbon atom to which it is attached, it forms in particular a structural moiety selected from C3-C6 cycloalkane-1,1-diyl, benzo C3-C6 cycloalkenediyl, 3- to 6-membered saturated or partially unsaturated benzo heterocyclic diyl, wherein the carbocyclic and heterocyclic rings are unsubstituted, partially or fully halogenated or carry 1 to 6 C1-C6 alkyl groups and wherein the heterocyclic ring preferably has 1 or 2 oxygen atoms as ring members.

[0127] In an embodiment of group (2), R 3 and R 4 Together with the carbon atom to which it is attached, it more particularly forms a structural moiety selected from C3-C6 cycloalkane-1,1-diyl or 3- to 6-membered saturated benzo heterocyclic diyl, wherein the carbocyclic and heterocyclic rings are unsubstituted, partially or fully halogenated or carry 1 to 6 C1-C6 alkyl groups, and wherein the heterocyclic group preferably has 1 or 2 oxygen atoms as ring members.

[0128] Embodiments of another specific group (2a) relate to diamino triazine compounds of the following formula (I), wherein R 3 and R 4 Together with the carbon atom to which it is attached, it forms C3-C6 cycloalkane-1,1-diyl, especially cyclopropane-1,1-diyl, cyclobutane-1,1-diyl, cyclopentane-1,1-diyl or cyclohexane-1,1-diyl, wherein the C3-C6 cycloalkane-1,1-diyl is unsubstituted, partially or fully halogenated or carries 1 to 6 C1-C6 alkyl groups, especially methyl. In an embodiment of group (2a), R 3 and R 4 Together with the carbon atom to which it is attached, it especially forms an unsubstituted C3-C6 cycloalkane-1,1-diyl.

[0129] Embodiments of another specific group (2b) relate to diamino triazine compounds of the following formula (I), wherein R 3 and R 4 Together with the carbon atom to which it is attached, it forms a 3- to 6-membered saturated benzo heterocyclic diyl, especially ethylene oxide-1,1-diyl, oxetane-1,1-diyl, oxane-1,1-diyl, oxane-1,1-diyl or oxane-4,4-diyl, the heterocyclic ring being unsubstituted, partially or fully halogenated or carrying 1 to 6 C1-C6 alkyl groups, especially the group, and wherein the heterocyclic ring preferably has 1 or 2 oxygen atoms as ring members. In an embodiment of group (2b), R 3 and R 4 Together with the carbon atom to which it is attached, it forms a 3- to 6-membered saturated benzo heterocyclic diyl, especially ethylene oxide-1,1-diyl, oxetane-1,1-diyl, oxane-1,1-diyl, oxane-1,1-diyl or oxane-4,4-diyl, the heterocyclic ring being unsubstituted.

[0130] CR 2 R 3 R 4 Particularly preferred examples of 2 R 3 R 4 are those groups in which R

[0131] Table 1a:

[0132]

[0133]

[0134] R 5 is H, OH, S(O)2NH2, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C3-C6 cycloalkyl)-C1-C4 alkyl, C1-C6 alkoxy, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, (C3-C6 cycloalkyl)-carbonyl, (C1-C6 alkyl)sulfonyl, (C1-C6 alkylamino)carbonyl, di(C1-C6 alkyl)aminocarbonyl, (C1-C6 alkylamino)sulfonyl, di(C1-C6 alkyl)aminosulfonyl and (C1-C6 alkoxy)sulfonyl, where the aliphatic and cycloaliphatic moieties of the above 15 groups are unsubstituted, partially or fully halogenated, phenyl, phenylsulfonyl, phenylaminosulfonyl, phenyl-C1-C6 alkyl, phenoxy, phenylcarbonyl and phenoxycarbonyl,

[0135] wherein the phenyl in the latter-mentioned 6 groups is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0136] preferably H, CN, C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkyl)carbonyl, (C3-C6 cycloalkyl)-carbonyl or (C1-C6 alkyl)sulfonyl, where the aliphatic moiety of the above 4 groups is unsubstituted, partially or fully halogenated;

[0137] phenyl and phenyl-C1-C6 alkyl,

[0138] wherein the phenyl in the latter-mentioned 2 groups is unsubstituted or substituted by 1, 2, 3, 4 or 5 identical or different substituents selected from halogen, CN, NO2, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy;

[0139] Especially H, CN, C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkyl)carbonyl, (C3-C6 cycloalkyl)-carbonyl or (C1-C6 alkyl)sulfonyl;

[0140] More especially H, CN, C1-C4 alkyl, (C1-C4 alkoxy)-C1-C4 alkyl, (C1-C4 alkyl)carbonyl, (C3-C6 cycloalkyl)-carbonyl, or (C1-C4 alkyl)sulfonyl;

[0141] Even more especially H, CN, CH3, CH2OCH3, C(O)CH3, C(O)cyclopropyl or SO2CH3; especially hydrogen.

[0142] Embodiments of other specific groups relate to diamino triazine compounds of formula (I) below, wherein R 6 is phenyl or a 5- or 6-membered heteroaryl, which is unsubstituted or bears 1, 2, 3, 4 or 5 groups R 6A which are selected from halogen, OH, CN, amino, NO2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkoxy, (C1-C6 alkoxy)-C2-C6 alkenyl, (C1-C6 alkoxy)-C2-C6 alkynyl, C1-C6 alkylthio, (C1-C6 alkyl)sulfinyl, (C1-C6 alkyl)sulfonyl, (C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkyl)-carbonyl, (C1-C6 alkoxy)-carbonyl, (C1-C6 alkyl)-carbonyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, (C3-C6 cycloalkyl)-C1-C4 alkyl, (C3-C6 cycloalkyl)-C1-C4 alkoxy, wherein the aliphatic and cycloaliphatic moieties of said groups are unsubstituted, partially or completely halogenated and wherein the cycloaliphatic moiety of said groups may bear 1, 2, 3, 4, 5 or 6 methyl groups,

[0143] wherein it is possible that R 6A are the same or different;

[0144] According to a preferred embodiment, R 6 is phenyl, which is unsubstituted or bears 1-5 groups R 6A which are selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl.

[0145] According to a preferred embodiment, R 6is a 5- or 6-membered heteroaryl which is unsubstituted or bears 1 or 5 groups R 6A , which are selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl.

[0146] R 6 Particularly preferred examples of R are given in lines 1-148 of Table 2a.

[0147] Table 2a:

[0148]

[0149]

[0150]

[0151]

[0152]

[0153] Embodiments of other specific groups relate to diamino triazine compounds of formula (I) below, wherein R 7 and R 7′ are independently of each other selected from hydrogen, halogen, C1-C4 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, preferably H and F.

[0154] Preferred are diamino triazine compounds of formula (I.a) corresponding to formula (I) below, wherein R 1 is hydrogen, R 2 is 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 above

[0155]

[0156] Particular embodiments of compound I are the following compounds:

[0157] I-A, I-B, I-C, I-D, I-E, I-F. In these formulas, the substituents, wherein R 1 and R 2 are hydrogen, Q is O, R a is F, R 4 is CH3, R 7R 7′ is H, H or F, F and R b1 、R b2 、R b3 and R 6 as defined in Table A:

[0158]

[0159]

[0160] Table 1-1 Compounds of Formula I-A, I-B, I-C, I-D, I-E, I-F, I-G, I-H, I-I, I-J, wherein for each individual compound R b1 、R b2 、R b3 and R 6 in combination corresponds in each case to a row of Table A (Compounds I-A.1-1.A-1 to I-A.1-1.A-384, I-B.1-1.A-1 to I-B.1-1.A-384, I-C.1-1.A-1 to I-C.1-1.A-384, I-D.1-1.A-1 to I-D.1-1.A-384, I-E.1-1.A-1 to I-E.1-1.A-384, I-F.1-1.A-1 to I-F.1-1.A-384, I-G.1-1.A-1 to I-G.1-1.A-384, I-H.1-1.A-1 to I-H.1-1.A-384, I-I.1-1.A-1 to I-I.1-1.A-384, I-J.1-1.A-1 to I-J.1-1.A-384).

[0161] Table A

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] The diamino triazine compounds of formula (I) according to the present invention can be prepared by standard methods of organic chemistry, for example, by the following methods:

[0173] Method A)

[0174] wherein R 1 is H, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy and R 5 is H, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy, (C1-C6 alkyl) carbonyl, the triazines of formula (I) can be prepared by reacting a halogenated triazine of formula (II) with an amine of formula (III) in the presence of a base and / or a catalyst or in the presence of an acid, as described in Scheme 1 below:

[0175]

[0176] The variables Q, R a , R b , R 2 , R 3 and R 4 , R 6 , R 7 and R 7′ have the meanings as in formula (I) above, especially the preferred meanings, and

[0177] Hal is halogen; preferably Cl or Br; particularly preferably Cl;

[0178] R 1 is H, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl or C1-C6 alkoxy; preferably R 1 is H or C1-C6 alkyl; particularly preferably R 1 is H; and

[0179] R 5 is H, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy or (C1-C6 alkyl) carbonyl; preferably R 5 is H, C1-C6 alkyl or (C1-C6 alkyl) carbonyl; particularly preferably R 5 is H or (C1-C6 alkyl) carbonyl; also particularly preferably R 5 is H; also particularly preferably R 5 is (C1-C6 alkyl) carbonyl; especially preferably R 5 is H.

[0180] The reaction of the triazine halides of formula (III) with the amine compounds of formula (II) is generally carried out in an inert organic solvent at a temperature of 50 °C to the boiling point of the reaction mixture, preferably 50 - 150 °C, particularly preferably 60 - 100 °C (e.g., P. Dao et al., Tetrahedron 2012, 68, 3856 - 3860).

[0181] The reaction can be carried out at atmospheric pressure or at elevated pressure, and if appropriate, continuously or batchwise under an inert gas.

[0182] The triazine halides of formula (III) and the compounds of formula (II) are used in equimolar amounts or the compounds of formula (II) are used in excess relative to the triazine halides of formula (III). Preferably, the molar ratio of the compounds of formula (II) to the triazine halides of formula (III) is 2:1 - 1:1, preferably 1.5:1 - 1:1, and particularly preferably 1.2:1.

[0183] The reaction of the triazine halides of formula (III) with the compounds of formula (II) is carried out in an organic solvent.

[0184] In principle, all solvents that can at least partially and preferably completely dissolve the triazine halides of formula (III) and the amines of formula (II) under the reaction conditions are suitable.

[0185] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane, and mixtures of C5 - C8 alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o - xylene, m - xylene, 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), dibutyl ether, anisole, and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N - dimethylformamide (DMF), N,N - dimethylacetamide (DMAC), 1,3 - dimethyl - 2 - imidazolidinone (DMI), N,N′ - dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), and 1 - methyl - 2 - pyrrolidone (NMP).

[0186] Preferred solvents are the ethers as defined above.

[0187] The term solvent as used herein also includes mixtures of two or more of the above - mentioned compounds.

[0188] The reaction of the triazine halides of formula (III) with the compounds of formula (II) is carried out in the presence of a base or an acid.

[0189] Examples of suitable bases include metal - containing bases and nitrogen - containing bases.

[0190] Examples of suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxides and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal formates, acetates and other metal salts of carboxylic acids, such as sodium formate, sodium benzoate, lithium acetate, sodium acetate, potassium acetate, magnesium acetate and calcium acetate; alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate and calcium carbonate, and alkali metal bicarbonates such as lithium bicarbonate, sodium bicarbonate, potassium bicarbonate; alkali metal and alkaline earth metal phosphates such as sodium phosphate, potassium phosphate and calcium phosphate; alkali metal and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and magnesium dimethoxide; in addition, there are also organic bases, such as tertiary amines such as tri-C1-C6 alkylamines, for example triethylamine, trimethylamine, N-ethyldiisopropylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and also bicyclic amines such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN).

[0191] Preferred bases are the alkali metal and alkaline earth metal alkoxides as defined above.

[0192] The term base as used herein also includes mixtures of two or more, preferably two, of the above compounds. It is particularly preferred to use one base.

[0193] The base can be used in excess, preferably 1-10 base equivalents, particularly preferably 2-4 base equivalents, based on the triazine halides of formula (VI), and they can also be used as solvents.

[0194] 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, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid.

[0195] Preferred acids are inorganic acids.

[0196] The acid is usually used in excess or, if appropriate, can be used as a solvent.

[0197] Work-up can be carried out in a known manner.

[0198] The end of the reaction can be readily determined by a person skilled in the art by means of conventional methods.

[0199] The reaction mixture is worked up in a conventional manner, for example by mixing with water, separating the phases and, if appropriate, purifying the crude product.

[0200] The amine compounds of the formula (II) required for the preparation of the compounds of the formula (I) are commercially available or can be prepared analogously to known literature procedures (for example Barnes et al., WO / 2007 / 067612).

[0201] For the preparation of the triazines of the formula (I) in which R 5 is H, C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl or C1-C6-alkoxy, the halo-triazines of the formula (VI) required are known from the literature, commercially available and / or can be prepared analogously to the known literature (for example J.K. Chakrabarti et al., Tetrahedron 1975, 31, 1879-1882) by reacting thio-triazines of the formula (IV) with a halogen source (for example Cl2) or another suitable halogenating agent (for example SOCl2):

[0202]

[0203] The variable R 2 、R 3 and R 4 have the meanings defined in formula (I) as described above, in particular the preferred meanings; Hal is halogen; preferably Cl or Br; particularly preferably Cl;

[0204] R* is C1-C6-alkyl, C2-C6-haloalkyl or phenyl; preferably C1-C6-alkyl or C2-C6-haloalkyl;

[0205] particularly preferably C1-C6-alkyl; very particularly preferably CH3; and

[0206] R 5 is H, C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy; particularly preferably H, C1-C6-alkoxy-C1-C6-alkyl or C1-C6-alkoxy; very particularly preferably H, CH2OCH3 or OCH3; more preferably hydrogen.

[0207] The reaction of the thio-triazines of the formula (IV) with the halogen (or halogenating agent) is generally carried out at from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to the boiling point of the reaction mixture, particularly preferably from 15-40 °C, in an inert organic solvent (for example J.K. Chakrabarti et al., Tetrahedron 1975, 31, 1879-1882).

[0208] The reaction can be carried out continuously or batchwise at atmospheric pressure or at elevated pressure, if appropriate under an inert gas.

[0209] In the process of the present invention, the halogen is used in excess relative to the thiotriazines of formula (IV).

[0210] The reaction of the thiotriazines of formula (IV) with the halogen is carried out in an organic solvent.

[0211] In principle, all solvents that can at least partially and preferably completely dissolve the thiotriazines of formula (IV) and the halogen under the reaction conditions are suitable.

[0212] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of C5-C8 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), di oxane, anisole and tetrahydrofuran (THF), alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, citric acid, trifluoroacetic acid.

[0213] Preferred solvents are the halogenated hydrocarbons and organic acids as defined above.

[0214] The term solvent as used herein also includes mixtures of two or more of the above compounds.

[0215] The end of the reaction can be easily determined by a person skilled in the art by means of conventional methods.

[0216] The reaction mixture is worked up in a conventional manner, for example by mixing with water, separating the phases and, if appropriate, purifying the crude product by chromatography.

[0217] The thiotriazines of formula (IV) required for the preparation of the halogenated triazines of formula (III) can be prepared by reacting a guanidine salt of formula (V) with a carbonyl compound of formula (VI) in the presence of a base:

[0218]

[0219] The variable R 2 、R 3 and R 4 have the meanings defined in formula (I) above, in particular the preferred meanings;

[0220] R* is C1-C6 alkyl, C2-C6 haloalkyl or phenyl; preferably C1-C6 alkyl or C2-C6 haloalkyl; particularly preferably C1-C6 alkyl; especially preferably CH3;

[0221] L 1is a leaving group capable of nucleophilic substitution, such as halogen, CN, C1-C6 alkoxy, C1-C6 alkylcarbonyloxy or C1-C6 alkoxycarbonyloxy; preferably halogen or C1-C6 alkoxy; particularly preferably Cl or C1-C6 alkoxy; still particularly preferably halogen; especially preferably Cl; and

[0222] L 2 is a leaving group capable of nucleophilic substitution, such as halogen, C1-C6 alkylsulfonyloxy, C1-C6 haloalkylsulfonyloxy, C1-C6 alkoxysulfonyloxy or phenylsulfonyloxy; preferably halogen or C1-C6 haloalkylsulfonyloxy; particularly preferably halogen; especially preferably Cl; and

[0223] R 5 is H, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy; particularly preferably H, C1-C6 alkoxy-C1-C6 alkyl or C1-C6 alkoxy; especially preferably H, CH2OCH3 or OCH3; more preferably hydrogen.

[0224] The reaction of the guanidine salt of formula (V) with the carbonyl compound of formula (VI) is generally carried out at a temperature of 50 °C to the boiling point of the reaction mixture, preferably 50 - 100 °C.

[0225] This reaction can be carried out continuously or batchwise at atmospheric pressure or under elevated pressure, and if appropriate, under an inert gas.

[0226] In one embodiment of the process of the present invention, the guanidine salt of formula (V) and the carbonyl compound of formula (VI) are used in equimolar amounts.

[0227] In another embodiment of the process of the present invention, the carbonyl compound of formula (VI) is used in excess relative to the guanidine salt of formula (V).

[0228] Preferably, the molar ratio of the carbonyl compound of formula (VI) to the guanidine salt of formula (V) is 1.5:1 - 1:1, preferably 1.2:1 - 1:1, particularly preferably 1.2:1, and still particularly preferably 1:1.

[0229] The reaction of the guanidine salt of formula (V) with the carbonyl compound of formula (VI) is generally carried out in an organic solvent.

[0230] In principle, all solvents that can at least partially and preferably completely dissolve the guanidine salt of formula (V) and the carbonyl compound of formula (VI) under the reaction conditions are suitable.

[0231] 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), di Alkanes, anisole, and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, and dipolar aprotic solvents such as sulfolane, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N′-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), and 1-methyl-2-pyrrolidone (NMP).

[0232] Preferred solvents are ethers and dipolar aprotic solvents as defined above.

[0233] More preferred solvents are ethers as defined above.

[0234] The term solvent as used herein also includes mixtures of two or more of the above compounds.

[0235] The reaction of the guanidine salt of formula (V) with the carbonyl compound of formula (VI) is carried out in the presence of a base.

[0236] Examples of suitable bases include metal-containing bases and nitrogen-containing bases.

[0237] Examples of suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal oxides and other metal oxides such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate and calcium carbonate, and alkali metal bicarbonates such as lithium bicarbonate, sodium bicarbonate, potassium bicarbonate; alkali metal and alkaline earth metal phosphates such as sodium phosphate, potassium phosphate and calcium phosphate; and in addition there are organic bases such as tertiary amines such as tri-C1-C6 alkylamines, for example triethylamine, trimethylamine, N-ethyldiisopropylamine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine, and also bicyclic amines such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN).

[0238] Preferred bases are tri-C1-C6 alkylamines as defined above.

[0239] The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. It is particularly preferred to use one base.

[0240] The bases are usually used in excess; but they can also be used in equimolar amounts or, if appropriate, used as solvents.

[0241] Based on the guanidine salt of formula (V), 1-5 base equivalents, particularly preferably 3 base equivalents of the base, are preferably used.

[0242] The end of the reaction can be easily determined by a person skilled in the art with the aid of conventional methods.

[0243] The reaction mixture is worked up in a conventional manner, for example by mixing with water, separating the phases and, if appropriate, purifying the crude product by chromatography.

[0244] The carbonyl compounds of the formula (VI) required for the preparation of the triazines of the formula (I) are known from the literature. They can thus be prepared and / or are commercially available.

[0245] For the preparation of the thiotriazines of the formula (IV), the guanidine salts of the formula (V) in which L 2 is iodine are 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).

[0246] Method B)

[0247] The triazines of the formula (I) can be prepared by reacting a halotriazine of the formula (II) with an amine of the formula (III) in the presence of a base and / or a catalyst or in the presence of an acid, as described in Scheme 2 below:

[0248]

[0249] The variables Q, R a , R b , R 2 , R 3 , R 4 , R 6 , R 7 and R 7′ have the meanings as in formula (I) above, in particular the preferred meanings, and

[0250] L 1 is a displaceable leaving group such as halogen, CN, C1 - C6 alkoxy, C1 - C6 alkoxycarbonyl, C1 - C6 alkylcarbonyloxy or C1 - C6 alkoxycarbonyloxy;

[0251] preferably halogen or C1 - C6 alkoxy;

[0252] particularly preferably Cl or C1 - C6 alkoxy, very particularly preferably halogen;

[0253] very particularly preferably Cl

[0254] R 1 is H, C1 - C6 alkyl, C1 - C6 alkoxy - C1 - C6 alkyl or C1 - C6 alkoxy; preferably R 1 is H or C1 - C6 alkyl; particularly preferably R 1is H; and

[0255] R 5 is H, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy or (C1-C6 alkyl)carbonyl; preferably R 5 is H, C1-C6 alkyl or (C1-C6 alkyl)carbonyl; particularly preferably R 5 is H or (C1-C6 alkyl)carbonyl; still particularly preferably R 5 is H; still particularly preferably R 5 is (C1-C6 alkyl)carbonyl; especially preferably R 5 is H.

[0256] The reaction of the biguanide of formula (VII) with the carbonyl compound of formula (VI) is generally carried out at a temperature of 50 °C to the boiling point of the reaction mixture, preferably 50 - 200 °C (for example, R. Sathunuru et al., J. Heterocycl. Chem. 2008, 45, 1673 - 1678).

[0257] This reaction can be carried out continuously or batchwise under atmospheric pressure or under elevated pressure, and if appropriate, under an inert gas.

[0258] In one embodiment of the process of the present invention, the biguanide of formula (VII) and the carbonyl compound of formula (VI) are used in equimolar amounts.

[0259] In another embodiment of the process of the present invention, the carbonyl compound of formula (VI) is used in excess relative to the biguanide of formula (VII).

[0260] Preferably, the molar ratio of the carbonyl compound of formula (VIII) to the biguanide of formula (VII) is 1.5:1 - 1:1, preferably 1.2:1 - 1:1, particularly preferably 1.2:1, and still particularly preferably 1:1.

[0261] The reaction of the biguanide of formula (VII) with the carbonyl compound of formula (VI) is carried out in an organic solvent.

[0262] In principle, all solvents that can at least partially and preferably completely dissolve the biguanide of formula (VII) and the carbonyl compound of formula (VI) under the reaction conditions are suitable.

[0263] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5-C8 alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-xylene, m-xylene 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), di Alkanes, anisole, and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N′-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), and 1-methyl-2-pyrrolidone (NMP).

[0264] Preferred solvents are the ethers and dipolar aprotic solvents as defined above. More preferred solvents are the ethers as defined above.

[0265] The term solvent as used herein also includes mixtures of two or more of the above compounds.

[0266] The reaction of the biguanide of formula (VII) with the carbonyl compound of formula (VIII) is carried out in the presence of a base.

[0267] Examples of suitable bases include metal-containing bases and nitrogen-containing bases.

[0268] Examples of suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal oxides, and other metal oxides such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide, and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride, alkali metal amides such as lithium amide, sodium amide, and potassium amide; alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate, and alkali metal bicarbonates such as lithium bicarbonate, sodium bicarbonate, and potassium bicarbonate; alkali metal and alkaline earth metal phosphates such as sodium phosphate, potassium phosphate, and calcium phosphate; and in addition there are organic bases such as tertiary amines such as tri-C1-C6 alkylamines, for example triethylamine, trimethylamine, N-ethyldiisopropylamine, and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine, and 4-dimethylaminopyridine (DMAP), and also bicyclic amines such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,5-diazabicyclo[4.3.0]non-5-ene (DBN).

[0269] Preferred bases are the tri-C1-C6 alkylamines as defined above. The term base as used herein also includes mixtures of two or more, preferably two of the above compounds. It is particularly preferred to use one base. The bases are generally used in excess; but they can also be used in equimolar amounts or, if appropriate, can be used as solvents. Based on the biguanide of formula (VII), preferably 1-5 base equivalents, particularly preferably 3 base equivalents of the base are used. The end of the reaction can be readily determined by a person skilled in the art by means of conventional methods.

[0270] The reaction mixture is worked up in a conventional manner, for example by mixing with water, separating the phases and, if appropriate, purifying the crude product by chromatography.

[0271] Some of the intermediates and end products are obtained as viscous oils, which can be purified or the volatile components removed under reduced pressure and at a moderately elevated temperature.

[0272] If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

[0273] The carbonyl compounds of formula (VI) required for the preparation of the pyrazines of formula (I) are known in the art and / or commercially available.

[0274] The biguanides of formula (VII) required for the preparation of the pyrazines of formula (I) can be prepared by reacting a cyanoguanidine of formula (IX) with an amine of formula (II) in the presence of an acid:

[0275]

[0276] wherein A is represented by the following structural moiety:

[0277]

[0278] The variables Q, R a , R b , R 2 , R 3 , R 4 , R 6 , R 7 and R 7′ have the meanings mentioned above in formula (I), in particular the preferred meanings, and

[0279] R 1 is H, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl or C1-C6 alkoxy; preferably R 1 is H or C1-C6 alkyl; particularly preferably R 1 is H; and

[0280] R 5 is H, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy or (C1-C6 alkyl)carbonyl; preferably R 5 is H, C1-C6 alkyl or (C1-C6 alkyl)carbonyl; particularly preferably R 5 is H or (C1-C6 alkyl)carbonyl; also particularly preferably R 5 is H; also particularly preferably R 5 is (C1-C6 alkyl)carbonyl; especially preferably R 5 is H.

[0281] The reaction of the guanidine of formula (IX) with the amine of formula (II) is generally carried out at 50 °C to 150 °C, preferably 80 °C to 130 °C.

[0282] If appropriate, microwave technology is used (e.g., C.O. Kappe, A. Stadler, Microwaves in Organic and Medicinal Chemistry, Weinheim 2012).

[0283] The reaction can be carried out continuously or batchwise at atmospheric pressure or at elevated pressure, if appropriate under an inert gas.

[0284] In one embodiment of the process according to the invention, the guanidine of formula (IX) and the amine of formula (II) are used in equimolar amounts.

[0285] In another embodiment of the process according to the invention, the amine of formula (II) is used in excess relative to the guanidine of formula (IX).

[0286] Preferably, the molar ratio of the amine of formula (II) to the guanidine of formula (IX) is 2:1 - 1:1, preferably 1.5:1 - 1:1, particularly preferably 1:1.

[0287] The reaction of the guanidine of formula (IX) with the amine of formula (II) is carried out in an organic solvent.

[0288] In principle, all solvents that can at least partially and preferably completely dissolve the guanidine of formula (IX) and the amine of formula (II) under the reaction conditions are suitable.

[0289] Examples of suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, nitromethane and mixtures of C5 - C8 alkanes, aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o - xylene, m - xylene 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), dibutyl ether, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, and dipolar aprotic solvents such as sulfolane, dimethyl sulfoxide, N,N - dimethylformamide (DMF), N,N - dimethylacetamide (DMAC), 1,3 - dimethyl - 2 - imidazolidinone (DMI), N,N′ - dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1 - methyl - 2 - pyrrolidone (NMP). Preferably, the solvents are ethers, nitriles and dipolar aprotic solvents as defined above.

[0290] More preferably, the solvents are nitriles as defined above.

[0291] ​

[0292] The term solvent as used herein also includes mixtures of two or more solvents.

[0293] The reaction of the guanidine of formula (IX) with the amine of formula (II) is carried out in the presence of an acid.

[0294] 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, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid.

[0295] The acid is usually used in excess or, where appropriate, can be used as a solvent.

[0296] Work-up can be carried out in a known manner.

[0297] The guanidine of formula (IX) required for the preparation of the biguanide of formula (VII) is commercially available or can be prepared according to literature procedures (e.g. J.L. LaMattina et al., J. Med. Chem. 1990, 33, 543 - 552; A. Perez-Medrano et al., J. Med. Chem. 2009, 52, 3366 - 3376).

[0298] The amine of formula (II) required for the preparation of the biguanide of formula (VII) is commercially available or can be prepared according to known literature procedures (e.g. Barnes et al., WO / 2007 / 067612).

[0299] The compounds of formula (I) have herbicidal activity. Accordingly, they can be used for controlling unwanted or undesired plants or plant growth. They can also be used in methods for controlling unwanted or undesired plants or plant growth, which methods comprise allowing at least one compound of formula (I) or a salt thereof to act on the plants, their environment or seeds. In order to allow the compound of formula (I) or a salt thereof to act on the plants, their environment or seeds, the compounds according to the invention are applied to the plants, their environment or the seeds of said plants.

[0300] To broaden the spectrum of action and to achieve a synergistic effect, the diamino-triazine compounds of formula (I) can be mixed with representatives of a large number of other herbicidal or growth-regulating active ingredient groups and subsequently applied simultaneously.

[0301] Components suitable for the mixtures are, for example, herbicides selected from the following classes: acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofurans, benzoic acids, benzothiadiazinones, bipyridines carbamates, chloroacetamides, chloro-carboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenols, diphenyl ethers, glycines, imidazolinones, iso- Azoles, iso- Oxazolidinones, nitriles, N-phenylphthalimides, Diazoles, Oxazolidinediones, hydroxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, aminophosphates, dithiophosphates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolecarboxamides, triazolepyrimidines, triones, uracils, ureas.

[0302] The present invention also relates to combinations of diamino-triazine compounds of formula (I) with at least one other herbicide B and / or at least one safener C).

[0303] Other herbicidal compounds B (component B) are especially selected from herbicides of classes b1)-b15):

[0304] b1) Lipid biosynthesis inhibitors;

[0305] b2) Acetolactate synthase inhibitors (ALS inhibitors);

[0306] b3) Photosynthesis inhibitors;

[0307] b4) Protoporphyrinogen-IX oxidase inhibitors,

[0308] b5) Bleaching herbicides;

[0309] b6) Enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

[0310] b7) Glutamine synthase inhibitors;

[0311] b8) 7,8-Dihydropteroate synthase inhibitors (DHP inhibitors);

[0312] b9) Mitosis inhibitors;

[0313] b10) Very long chain fatty acid synthesis inhibitors (VLCFA inhibitors);

[0314] b11) Cellulose biosynthesis inhibitors;

[0315] b12) Decoupler herbicides;

[0316] b13) Auxin herbicides;

[0317] b14) Auxin transport inhibitors; and

[0318] b15) Other herbicides selected from: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleichydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methylbromide, methyl-dymron, methyliodide, MSMA, oleicacid, chloro oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters;

[0319] including their agriculturally applicable salts or derivatives such as ethers, esters or amides.

[0320] Those compositions of the invention preferably comprising at least one herbicide B selected from the herbicides of groups b1, b6, b9, b10 and b11.

[0321] Examples of herbicide B which can be used in combination with the compounds of formula (I) according to the invention are:

[0322] b1) Lipid biosynthesis inhibitors selected from: ACC herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, high fenoxaprop-P, high fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, Metamifop, Pinoxaden, Profoxydim, Propaquizafop, Quizalofop, Quizalofop-ethyl, Quizalofop-tefuryl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-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-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3), 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5), 4-(2',4'-Dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3), 5-Acetoxy-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312337-48-6), 5-Acetoxy-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one, 5-Acetoxy-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1), 5-Acetoxy-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2), 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,Methyl 6 - tetramethyl - 5 - oxo - 2H - pyran - 3 - carboxylate (CAS 1312337 - 51 - 1), methyl 4-(2',4'-dichloro - 4 - cyclopropyl - [1,1'-biphenyl]-3 - yl)-5,6 - dihydro - 2,2,6,6 - tetramethyl - 5 - oxo - 2H - pyran - 3 - carboxylate, methyl 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 - carboxylate (CAS 1312340 - 83 - 2), methyl 4-(2',4'-dichloro - 4 - ethyl[1,1'-biphenyl]-3 - yl)-5,6 - dihydro - 2,2,6,6 - tetramethyl - 5 - oxo - 2H - pyran - 3 - carboxylate (CAS 1033760 - 58 - 5); and non - ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate, and vernolate;

[0323] b2) ALS inhibitors selected from the following: sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl,Trifloxysulfuron, triflusulfuron, triflusulfuron-methyl, and tritosulfuron; imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, and imazethapyr; triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan, and pyroxsulam; pyrimidinyl benzoate herbicides such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 1-methylethyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (CAS 420138-41-6), propyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylamine (CAS 420138-01-8); sulfonylaminocarbonyltriazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone, and thiencarbazone-methyl; and triafamone; wherein a preferred embodiment of the present invention relates to those compositions comprising at least one imidazolinone herbicide;

[0324] b3) Photosynthesis inhibitors selected from the following: amicarbazone, a photosystem II inhibitor such as triazine herbicides including chloro-triazines, triazinones, triazinediones, methylthio-triazines and pyridazinones, such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin; arylureas such as chlorobromuron, chlorotoluron, chloroxuron, butyl Dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thidiazuron, phenylcarbamates such as desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uracils such as bromacil, lenacil and terbacil, and bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil, and photosystem I inhibitors such as diquat cation, diquat-dibromide, paraquat cation, paraquat-dichloride and paraquat-dimetilsulfate. One preferred embodiment of the present invention relates to those compositions comprising at least one arylurea herbicide. One preferred embodiment of the present invention also relates to those compositions comprising at least one triazine herbicide. One preferred embodiment of the present invention also relates to those herbicides comprising at least one nitrile herbicide;

[0325] b4) Protoporphyrinogen-IX oxidase inhibitors selected from the following: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, propargyl oxadiargyl, oxadiazon, oxyfluorfen, pentyl oxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetic acid ethyl ester (CAS 353292-31-6;

[0326] S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4] [0000973]azin-6-yl]-1,5-dimethyl-6-thio-[1,3,5]triazinan-2,4-dione, 1,5-dimethyl-6-thio-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[b][1,4] [0000974]azin-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[b][1,4] [0000975]azin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione, 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4] [0000976]azin-6-yl)-1H-pyrimidine-2,4-dione, (E)-methyl 4-[2-chloro-5-(4-chloro-5-difluoromethoxy-1H-methylpyrazol-3-yl)-4-fluorophenoxy]-3-methoxybut-2-enoate (CAS 948893-00-3) and 3-[7-chloro-5-fluoro-2-trifluoromethyl-1H-benzimidazol-4-yl]-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione (CAS 212754-02-4);

[0327] b5) A bleaching herbicide selected from the following: PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7); HPPD inhibitors: benzobicyclon, benzofenap, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, and bicyclopyrone; bleaching agents; unknown targets: aclonifen, amitrole, and flumeturon; isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, and bicyclopyrone; bleaching agents; unknown targets: aclonifen, amitrole, and flumeturon;

[0328] b6) An EPSP synthase inhibitor selected from the following: glyphosate, glyphosate-isopropylammonium, glyphosate-potassium, and glyphosate-trimesium (sulfosate);

[0329] b7) A glutamine synthetase inhibitor selected from the following: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, and glufosinate-ammonium;

[0330] b8) A DHP synthase inhibitor selected from the following: asulam;

[0331] b9) A mitotic inhibitor selected from the following: Group K1 compounds: Dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, and trifluralin; aminophosphates such as amiprophos, amiprophos-methyl, and butamiphos; benzoic acid herbicides such as chlorthal and chlorthal-dimethyl; pyridines such as dithiopyr and thiazopyr; benzamides such as propyzamide and tebutam; Group K2 compounds: Chlorpropham, propham, and carbetamide; among which Group K1 compounds are preferred, and dinitroanilines are particularly preferred;

[0332] b10) VLCFA inhibitors selected from the following: chloroacetamides such as acetochlor, alachlor, butachlor, dimethachlor, dimethanamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor, and thenylchlor; hydroxyacetanilides such as flufenacet and mefenacet; acetanilides such as diphenamid, naproanilide, napropamide, and napropamide-M; tetrazolinones such as fentrazamide; and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, and the isomers of II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8, and II.9 oxazoline compounds:

[0333]

[0334]

[0335] The isomers of formula (II) are known in the art, for example, from WO 2006 / 024820, WO2006 / 037945, WO 2007 / 071900, and WO 2007 / 096576;

[0336] Among the VLCFA inhibitors, chloroacetamides and hydroxyacetanilides are preferred;

[0337] b11) Cellulose biosynthesis inhibitors selected from the following: chlorthiamid, dichlobenil, flupoxam, isoxaben, and 1-cyclohexyl-5-pentafluorophenoxy-1 4 ​-[1,2,4,6]Thiatriazin-3-ylamine:

[0338] b12) A decoupling herbicide selected from: dinoseb, dinoterb, and DNOC and their salts;

[0339] b13) An auxin herbicide selected from: 2,4-D and its salts and esters, such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen 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-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA(2,3,6) and its salts and esters, and triclopyr and its salts and esters;

[0340] b14) An auxin transport inhibitor selected from: diflufenzopyr, diflufenzopyr-sodium, naptalam, and naptalam-sodium;

[0341] b15) Other herbicides selected from the following: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleichydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyliodide, MSMA, oleic acid, chloro aziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, and tridiphane. Preferred herbicide B that can be used in combination with the compound of formula (I) of the present invention is:

[0342] b1) Lipid biosynthesis inhibitors selected from the following: clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, high Fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, Metamifop, Pinoxaden, Profoxydim, Propaquizafop, Quizalofop-P-ethyl, Quizalofop-P-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-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3), 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5), 4-(2',4'-Dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3), 5-Acetoxy-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-Acetoxy-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one, 5-Acetoxy-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1), 5-Acetoxy-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2), Methyl 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-carboxylate (CAS1312337-51-1), 4-(2',4'-Dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,Methyl 6 - tetramethyl - 5 - oxo - 2H - pyran - 3 - carboxylate, methyl 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 - carboxylate (CAS 1312340 - 83 - 2), methyl 4-(2',4'-dichloro - 4 - ethyl[1,1'-biphenyl]-3-yl)-5,6 - dihydro - 2,2,6,6 - tetramethyl - 5 - oxo - 2H - pyran - 3 - carboxylate (CAS 1033760 - 58 - 5), benfuresate, dimepiperate, EPTC, esprocarb, ethofumesate, molinate, orbencarb, prosulfocarb, thiobencarb, and triallate;

[0343] b2) ALS inhibitors selected from the following: amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-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, propoxycarbazon-sodium, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid,pyriminobac-methyl, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron and triafamone;

[0344] b3) photosynthesis inhibitors selected from the group consisting of: ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromoxynil and its salts and esters, chloridazone, chlorotoluron, cyanazine, desmedipham, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, lenacil, linuron, metamitron, methabenzthiazuron, metribuzin, paraquat cation, paraquat-dichloride, phenmedipham, propanil, pyridate, simazine, terbutryn, terbuthylazine and thidiazuron;

[0345] b4) Protoporphyrinogen-IX oxidase inhibitors selected from the following: acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon-ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flu mioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, propar gyl-oxadiargyl, oxadiazon, oxyfluorfen, pen toxazone, pyraflufen-ethyl, saflufenacil, sulfentrazone, tiafenacil, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4] oxazin-6-yl]-1,5-dimethyl-6-thio-[1,3,5]triazinan-2,4-dione, 1,5-dimethyl-6-thio-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[b][1,4] (6 - (2,2,7 - trifluoro - 3 - oxo - 4 - prop - 2 - yn - 1 - yl - 3,4 - dihydro - 2H - benzo[b][1,4]triazin - 6 - yl)[1,3,5]triazinan - 2,4 - dione (CAS 1258836 - 72 - 4), 2 - (2,2,7 - trifluoro - 3 - oxo - 4 - prop - 2 - yn - 1 - yl - 3,4 - dihydro - 2H - benzo[b][1,4] (6 - (2,2,7 - trifluoro - 3 - oxo - 4 - prop - 2 - yn - 1 - yl - 3,4 - dihydro - 2H - benzo[1,4]triazin - 6 - yl) - 4,5,6,7 - tetrahydroisoindole - 1,3 - dione, 1 - methyl - 6 - (trifluoromethyl) - 3 - (2,2,7 - trifluoro - 3 - oxo - 4 - prop - 2 - yn - 1 - yl - 3,4 - dihydro - 2H - benzo[1,4] (6 - (2,2,7 - trifluoro - 3 - oxo - 4 - prop - 2 - yn - 1 - yl - 3,4 - dihydro - 2H - benzo[1,4]triazin - 6 - yl) - 1H - pyrimidine - 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);

[0346] b5) a bleaching herbicide selected from: aclonifen, amitrole, beflubutamid, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquintrione, flumeturon, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfotole, pyrazolynate, sulcotrione, tefuryltrione, tembotrione, topramezone and 4 - (3 - (trifluoromethyl)phenoxy) - 2 - (4 - (trifluoromethyl)phenyl)pyrimidine (CAS 180608 - 33 - 7);

[0347] b6) an EPSP synthase inhibitor selected from: glyphosate, glyphosate - isopropylammonium, glyphosate - potassium and glyphosate - trimesium (sulfosate);

[0348] b7) a glutamine synthetase inhibitor selected from: glufosinate, glufosinate - P and glufosinate - ammonium;

[0349] b8) A DHP synthase inhibitor selected from the following: asulam;

[0350] b9) A mitosis inhibitor selected from the following: benfluralin, dithiopyr, ethalfluralin, oryzalin, pendimethalin, thiazopyr, and trifluralin;

[0351] b10) A VLCFA inhibitor selected from the following: acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethanamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone, thenylchlor, and 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 described above; isoxazoline compounds;

[0352] b11) A cellulose biosynthesis inhibitor selected from the following: dichlobenil, flupoxam, isoxaben, and 1-cyclohexyl-5-pentafluorophenoxy-1 4 -[1,2,4,6]thiatriazin-3-ylamine;

[0353] b13) Auxin herbicides selected from the following: 2,4-D and its salts and esters, cloproxydim and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, and triclopyr and its salts and esters;

[0354] b14) Auxin transport inhibitors selected from the following: diflufenzopyr and diflufenzopyr-sodium;

[0355] b15) Other herbicides selected from the following: bromobutide, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, difenzoquat, difenzoquat-metilsulfate, DSMA, dymron (=daimuron), flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, indanofan, indaziflam, metam, methyl bromide, MSMA, chlorine Oxaziclomefone, pyributicarb, triaziflam and tridiphane. Particularly preferred herbicides B that can be used in combination with the compound A of formula (I) of the present invention are:

[0356] b1) Lipid biosynthesis inhibitors selected from: Clodinafop-propargyl, Cycloxydim, Cyhalofop-butyl, High Fenoxaprop-P-ethyl, Pinoxaden, Profoxydim, 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-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3), 4-(4'-Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5), 4-(2',4'-Dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3), 5-Acetoxy-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-Acetoxy-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one, 5-Acetoxy-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312340-82-1), 5-Acetoxy-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2), Methyl 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-carboxylate (CAS 1312337-51-1), 4-(2',4'-Dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-carboxylate, Methyl 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-carboxylate (CAS 1312340-83-2), 4-(2',Methyl (4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-carboxylate (CAS 1033760-58-5), esprocarb, prosulfocarb, thiobencarb, and triallate;,

[0357] b2) ALS inhibitors selected from the group consisting of: bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsulam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon-methyl, tritosulfuron, and triafamone;

[0358] b3) Photosynthesis inhibitors selected from the group consisting of ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat cation, paraquat dichloride, propanil, terbutryn, and terbuthylazine;

[0359] b4) Protoporphyrinogen-IX oxidase inhibitors selected from the group consisting of flumioxazin, oxyfluorfen, saflufenacil, sulfentrazone, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-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-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[b][1,4] oxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione, and 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4] oxazin-6-yl)-1H-pyrimidine-2,4-dione; b5) Bleaching herbicides selected from the group consisting of amitrole, bicyclopyrone, clomazone, diflufenican, fenquintrione, flumeturon, flurochloridone, iso

[0360] ... isoxaflutole, mesotrione, picolinafen, sulcotrione, tefuryltrione, tembotrione and topramezone;

[0361] b6) EPSP synthase inhibitors selected from: glyphosate, glyphosate-isopropylammonium and sulfosate;

[0362] b7) Glutamine synthetase inhibitors selected from: glufosinate, glufosinate-P and glufosinate-ammonium;

[0363] b9) Mitosis inhibitors selected from: pendimethalin and trifluralin;

[0364] b10) VLCFA inhibitors selected from: acetochlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone; Isoxazoline compounds of the formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as described above are also preferred; oxazoline compounds;

[0365] b11) Cellulose biosynthesis inhibitors selected from: isoxaben;

[0366] b13) auxin herbicides selected from the group consisting of 2,4-D and its salts and esters such as clacyfos, cyprodinil 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;

[0367] b14) an auxin transport inhibitor selected from the group consisting of diflufenzopyr and diflufenzopyr-sodium;

[0368] b15) Other herbicides selected from the group consisting of dymron (= daimuron), indanofan, indaziflam, chlorpyrifos Oxazicclomefone.

[0369] The active compounds B and C having a carboxyl group can be used in the compositions according to the invention in the form of the acid, in the form of agriculturally acceptable salts or in the form of agriculturally acceptable derivatives, as described above.

[0370] In the case of dicamba, suitable salts include those in which the counterion is an agriculturally available cation. For example, suitable salts of dicamba are dicamba sodium (dicamba-sodium), dicamba potassium (dicamba-potassium), dicamba methylammonium (dicamba-methylammonium), dicamba dimethylammonium (dicamba-dimethylammonium), dicamba isopropylammonium (dicamba-isopropylammonium), dicamba diglycolamine (dicamba-diglycolamine), dicamba ethanolamine (dicamba-olamine), dicamba diethanolamine (dicamba-diolamine), dicamba triethanolamine (dicamba-trolamine), dicamba-N, N-bis (3-aminopropyl) methylamine and dicamba-diethylenetriamine. The example of suitable ester is dicamba methyl ester (dicamba-methyl) and dicamba butoxyethyl ester (dicamba-butoyl).

[0371] Suitable salts of 2,4-D are ammonium 2,4-D, dimethylammonium 2,4-D, diethylammonium 2,4-D, diethanolammonium 2,4-D (2,4-D diolamine), triethanolammonium 2,4-D, isopropylammonium 2,4-D, triisopropanolammonium 2,4-D, heptylammonium 2,4-D, dodecylammonium 2,4-D, tetradecylammonium 2,4-D, triethylammonium 2,4-D, tris(2-hydroxypropyl)ammonium 2,4-D, triisopropylammonium 2,4-D, triethanolamine 2,4-D, lithium 2,4-D, sodium 2,4-D. Examples of suitable esters of 2,4-D are butoxyethyl 2,4-D (2,4-D-butotyl), 2-butoxypropyl 2,4-D, 3-butoxypropyl 2,4-D, butyl 2,4-D (2,4-D-butyl), ethyl 2,4-D (2,4-D-ethyl), ethylhexyl 2,4-D (2,4-D-ethylhexyl), isobutyl 2,4-D (2,4-D-isobutyl), isooctyl 2,4-D (2,4-D-isooctyl), isopropyl 2,4-D (2,4-D-isopropyl), meptyl 2,4-D (2,4-D-meptyl), methyl 2,4-D (2,4-D-methyl), octyl 2,4-D (2,4-D-octyl), pentyl 2,4-D (2,4-D-pentyl), propyl 2,4-D (2,4-D-propyl), tetrahydrofuryl 2,4-D (2,4-D-tefuryl) and clacyfos.

[0372] Suitable salts of 2,4-DB are, for example, sodium 2,4-DB, potassium 2,4-DB and dimethylammonium 2,4-DB. Suitable esters of 2,4-DB are, for example, butyl 2,4-DB (2,4-DB-butyl) and isooctyl 2,4-DB (2,4-DB-isoctyl).

[0373] Suitable salts of dichlorprop are, for example, dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-butotyl and dichlorprop-isoctyl.

[0374] Suitable salts and esters of MCPA include MCPA-butotyl, 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.

[0375] A suitable salt of MCPB is MCPB-sodium. A suitable ester of MCPB is MCPB-ethyl.

[0376] Suitable salts of clopyralid are clopyralid-potassium, clopyralid-ethanolammonium, and clopyralid-tri-(2-hydroxypropyl)ammonium. Examples of suitable esters of clopyralid are methyl clopyralid.

[0377] Examples of suitable esters of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1-methylethyl, with fluroxypyr-meptyl being preferred.

[0378] Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram-triisopropanolammonium, picloram-triisopropylammonium, and picloram-trolamine. A suitable ester of picloram is picloram-isoctyl.

[0379] Suitable salts of triclopyr are triclopyr-triethylammonium. Suitable esters of triclopyr are, for example, triclopyr-ethyl and triclopyr-butotyl.

[0380] Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA dimethylammonium, 2,3,6-TBA lithium, 2,3,6-TBA potassium and 2,3,6-TBA sodium.

[0381] Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid-dimethylammonium and aminopyralid-tris(2-hydroxypropyl)ammonium.

[0382] Suitable salts of glyphosate are, for example, glyphosate ammonium salt, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate isopropylammonium salt, glyphosate potassium, glyphosate-sodium, sulfosate, and ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate isopropylammonium salt and sulfosate.

[0383] A suitable salt of glufosinate is, for example, glufosinate ammonium salt.

[0384] Suitable salts of glufosinate-P are, for example, glufosinate-P-ammonium.

[0385] Suitable salts and esters of bromoxynil are, for example, bromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.

[0386] Suitable salts and esters of ioxynil are, for example, ioxynil octanoate, ioxynil potassium, and ioxynil sodium.

[0387] Suitable salts and esters of mecoprop include mecoprop butotyl, mecoprop dimethylammonium, mecoprop diolamine, mecoprop ethadyl, mecoprop 2-ethylhexyl, mecoprop isooctyl, mecoprop methyl, mecoprop potassium, mecoprop sodium, and mecoprop trolamine.

[0388] Suitable salts of mecoprop-P include mecoprop-P butotyl, mecoprop-P dimethylammonium, mecoprop-P 2-ethylhexyl, mecoprop-P isobutyl, mecoprop-P potassium, and mecoprop-P sodium.

[0389] A suitable salt of diflufenican is, for example, diflufenican sodium.

[0390] A suitable salt of naptalam is, for example, naptalam sodium.

[0391] Suitable salts and esters of cyprodinil include cyprodinil dimethylammonium, cyprodinil methyl ester, cyprodinil triisopropanolammonium, cyprodinil sodium, and cyprodinil potassium.

[0392] A suitable salt of quinclorac is, for example, quinclorac dimethylammonium.

[0393] A suitable salt of quinclorac is, for example, quinclorac dimethylammonium.

[0394] A suitable salt of imazapic is, for example, imazapic ammonium.

[0395] Suitable salts of imazapic are, for example, imazapic ammonium and imazapic isopropylammonium.

[0396] Suitable salts of imazapyr are, for example, imazapyr ammonium and imazapyr isopropylammonium.

[0397] Suitable salts of imazaquin are, for example, imazaquin ammonium.

[0398] Suitable salts of imazethapyr are, for example, imazethapyr ammonium and imazethapyr isopropylammonium.

[0399] Suitable salts of topramezone are, for example, topramezone sodium.

[0400] Particularly preferred herbicidal compound B is herbicide B as defined above; in particular, herbicides B.1 - B.203 listed in Table B below:

[0401] Table B:

[0402]

[0403]

[0404]

[0405] In addition, the compound of formula (I) can be usefully applied in combination with a safener and optionally one or more other herbicides. A safener is a compound that prevents or reduces damage to useful plants but has no significant effect on the herbicidal action of the compound of formula (I) on unwanted plants. They can be applied before sowing (e.g., during seed treatment, on cuttings or seedlings) or in a pre - emergence or post - emergence application manner to useful plants. The safener and the compound of formula (I) and optionally herbicide B can be applied simultaneously or sequentially.

[0406] Suitable safeners are, for example, (quinolin - 8 - yloxy) acetic acids, 1 - phenyl - 5 - haloalkyl - 1H - 1,2,4 - triazole - 3 - carboxylic acids, 1 - phenyl - 4,5 - dihydro - 5 - alkyl - 1H - pyrazole - 3,5 - dicarboxylic acids, 4,5 - dihydro - 5,5 - diaryl - 3 - isoxazolecarboxylic acids, dichloroacetamides, α - oximinophenylacetonitriles, acetophenone oximes, 4,6 - dihalo - 2 - phenylpyrimidines, N - [[4 - (aminocarbonyl)phenyl]sulfonyl] - 2 - benzamides, 1,8 - naphthalic anhydride, 2 - halo - 4 - haloalkyl - 5 - thiazolecarboxylic acids, thiophosphates and N - alkyl - O - phenylcarbamates and their agriculturally useful salts and their agriculturally useful derivatives such as amides, esters and thioesters, provided that they have acid groups.

[0407] ​Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, bisbenz oxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (MON 4660, CAS 71526-07-3), 2,2,5-trimethyl-3-dichloroacetyl-1,3- oxazolidine (R-29148, CAS 52836-31-4) and N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide (CAS 129531-12-0).

[0408] Particularly preferred safeners C are the following compounds C.1 - C.17 listed in Table C:

[0409] Table C

[0410]

[0411]

[0412] Active compounds B of the classes b1) - b15) and safener compounds C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000, Volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995; W. H. Ahrens, Herbicide Handbook, 7th Edition, Weed Science Society of America, 1994 and K. K. Hatzios, Herbicide Handbook, Supplement to the 7th Edition, Weed Science Society of America, 1998. 2,2,5 - Trimethyl - 3 - dichloroacetyl - 1,3 - oxazolidine [CAS 52836 - 31 - 4] is also known as R - 29148. 4 - Dichloroacetyl - 1 - oxa - 4 - azaspiro[4.5]decane [CAS 71526 - 07 - 3] is also known as AD - 67 and MON4660.

[0413] The attribution of the corresponding mode of action of the active compounds is based on the current knowledge. If several modes of action apply to an active compound, the substance is assigned to only one mode of action.

[0414] The following combinations designated by the codes A - X.Y.Z represent specific embodiments of the invention:

[0415] A - 1.1.1 to A - 1.384.3671,

[0416] A - 2.1.1 to A - 2.384.3671,

[0417] A - 3.1.1 to A - 3.384.3671,

[0418] A - 4.1.1 to A - 4.384.3671,

[0419] A - 5.1.1 to A - 5.384.3671,

[0420] A - 6.1.1 to A - 6.384.3671,

[0421] A - 7.1.1 to A - 7.384.3671,

[0422] A-8.1.1 to A-8.384.3671,

[0423] A-9.1.1 to A-9.384.3671,

[0424] A-10.1.1 to A-10.384.3671,

[0425] A-11.1.1 to A-11.384.3671,

[0426] A-12.1.1 to A-12.384.3671,

[0427] A-13.1.1 to A-13.384.3671,

[0428] A-14.1.1 to A-14.384.3671,

[0429] A-15.1.1 to A-15.384.3671,

[0430] A-16.1.1 to A-16.384.3671,

[0431] A-17.1.1 to A-17.384.3671,

[0432] A-18.1.1 to A-18.384.3671,

[0433] A-19.1.1 to A-19.384.3671,

[0434] A-20.1.1 to A-20.384.3671,

[0435] A-21.1.1 to A-21.384.3671,

[0436] A-22.1.1 to A-22.384.3671,

[0437] A-23.1.1 to A-23.384.3671,

[0438] A-24.1.1 to A-24.384.3671,

[0439] A-25.1.1 to A-25.384.3671,

[0440] A-26.1.1 to A-26.384.3671,

[0441] A-27.1.1 to A-27.384.3671,

[0442] A-28.1.1 to A-28.384.3671,

[0443] A-29.1.1 to A-29.384.3671,

[0444] A-30.1.1 to A-30.384.3671,

[0445] A-31.1.1 to A-31.384.3671,

[0446] A-32.1.1 to A-32.384.3671,

[0447] A-33.1.1 to A-33.384.3671,

[0448] A-34.1.1 to A-34.384.3671,

[0449] A-35.1.1 to A-35.384.3671.

[0450] In the above code, A-X refers to the numbers of groups A-1 to A-35. The integer Y refers to the rows of Table A, and the integer Z refers to the rows of Table 1 below.

[0451] Thus, the code A-1.1.1 refers to the combination of the compound of formula I.a of group A-1 (where R b1 , R b2 , R b3 and R 6 are defined in the first row of Table A) with herbicide B and safener C as defined by combination number 1.1 of Table 1.

[0452] The code A-12.2.35 refers to the combination of the compound of formula I.a of group A-12 (where R b1 , R b2 , R b3 and R 6 are defined in the second row of Table A) with herbicide B and safener C as defined by combination number 1.35 of Table 1.

[0453] The code A-35.300.3671 refers to the combination of the compound of formula I.a of group A-35 (where R b1 , R b2 , R b3 and R 6 are defined in the 300th row of Table A) with herbicide B and safener C as defined by combination number 1.3671 of Table 1.

[0454] Table 1

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481] Furthermore, it may be advantageous to apply 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 controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with inorganic salt solutions for treating nutrient and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.

[0482] The invention also relates to agrochemical compositions comprising at least one adjuvant and at least one diaminotriazine compound of formula (I) according to the invention.

[0483] The agrochemical compositions comprise a pesticidally effective amount of a diaminotriazine compound of formula (I). The term "effective amount" means an amount of the composition or of compound I which is sufficient to control unwanted plants, especially in cultivated plants, without causing significant damage to the plants being treated. This amount can vary within wide limits and depends on various factors such as the plants to be controlled, the cultivated plants or materials being treated, the climatic conditions and the particular diaminotriazine compound of formula (I) used.

[0484] The diaminotriazine compounds of formula (I), their N-oxides or salts can be converted into the types customary for agrochemical compositions, for example solutions, emulsions, suspensions, powders, dusts, pastes, granules, tablets, 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, pills, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), tablets (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), pesticidal articles (e.g. LN) and gel formulations (e.g. GF) for treating plant propagation material such as seeds. These and other types of agrochemical compositions are defined in "Catalogue of pesticide formulation types and international coding system", Technical Monograph, No. 2, 6th Edition, May 2008, CropLife International.

[0485] Agrochemical compositions are prepared in a known manner as described, for example, in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0486] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, fungicides, antifreezes, defoamers, colorants, tackifiers and binders.

[0487] Suitable solvents and liquid carriers are water and organic solvents such as middle to high-boiling mineral oil fractions, for example kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, for example cyclohexanone; esters, for example lactate, carbonate, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0488] Suitable solid carriers or fillers are mineral earths, for example silicates, silica gels, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, for example cellulose, starch; fertilizers, for example ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of plant origin, for example cereal flours, bark flours, wood flours and nut shell flours, and mixtures thereof.

[0489] Suitable surfactants are surface-active compounds such as anionic, cationic, non-ionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants. Examples of surfactants are listed in McCutcheon’s, Volume 1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0490] Suitable anionic surfactants are the alkali metal, alkaline earth metal or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, carboxylic acids and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, dodecyl- and tridecylbenzene sulfonates, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

[0491] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl 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 to 50 equivalents of alkylene oxide. Ethylene oxide and / or propylene oxide can be used for alkoxylation, with ethylene oxide being preferred. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or glycerol monoesters. Examples of glycosyl surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate.

[0492] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds having 1 or 2 hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are A-B or A-B-A type block polymers containing blocks of polyoxyethylene and polyoxypropylene, or A-B-C type block polymers containing alkanol, polyoxyethylene and polyoxypropylene. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyethylenamine.

[0493] Suitable adjuvants are compounds that have negligible pesticidal activity by themselves or even no pesticidal activity by themselves and improve the biological properties of Compound I against the target. Examples are surfactants, mineral oils or vegetable oils and other auxiliaries. Other examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[0494] Suitable thickeners are polysaccharides (such as xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0495] Suitable bactericides are bronopol and isothiazolinone derivatives such as alkyl isothiazolinones and benzisothiazolinones.

[0496] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol.

[0497] Suitable defoamers are polysiloxanes, long-chain alcohols and fatty acid salts.

[0498] Suitable colorants (e.g., red, blue or green) are poorly water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (such as iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (such as alizarin colorants, azo colorants and phthalocyanine colorants).

[0499] Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological waxes or synthetic waxes, and cellulose ethers.

[0500] Examples of types of agrochemical compositions and their preparation are:

[0501] i) Water-soluble concentrates (SL, LS)

[0502] 10 - 60% by weight of the diaminotriazine compound of formula (I) according to the invention and 5 - 278% by weight of a wetting agent (such as an alcohol alkoxylate) are dissolved in water and / or a water-soluble solvent (such as an alcohol) up to 100% by weight. The active substance dissolves upon dilution with water.

[0503] ii) Dispersible concentrates (DC)

[0504] 5 - 25% by weight of the diaminotriazine compound of formula (I) according to the invention and 1 - 10% by weight of a dispersant (such as polyvinylpyrrolidone) are dissolved in an organic solvent (such as cyclohexanone) up to 100% by weight. Dilution with water gives a dispersion.

[0505] iii) Emulsifiable concentrates (EC)

[0506] 278 - 70% by weight of the diaminotriazine compound of formula (I) according to the invention and 5 - 10% by weight of an emulsifier (such as calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (such as an aromatic hydrocarbon) up to 100% by weight. Dilution with water gives an emulsion.

[0507] iv) Emulsions (EW, EO, ES)

[0508] Dissolve 5 - 40% by weight of the diamino - triazine compound of formula (I) of the present invention and 1 - 10% by weight of an emulsifier (such as calcium dodecylbenzenesulfonate and castor oil ethoxylate) in 20 - 40% by weight of a water - insoluble organic solvent (such as aromatic hydrocarbons). Introduce this mixture into water up to 100% by weight with the aid of an emulsifier to form a homogeneous emulsion. Dilute with water to obtain an emulsion.

[0509] v) Suspensions (SC, OD, FS)

[0510] In a stirred ball mill, comminute 20 - 60% by weight of the diamino - triazine compound of formula (I) of the present invention in the presence of 2 - 10% by weight of a dispersant and wetting agent (such as sodium lignosulfonate and alcohol ethoxylate), 0.1 - 2% by weight of a thickener (such as xanthan gum) and water up to 100% by weight to obtain a finely divided suspension of the active substance. Dilute with water to obtain a stable suspension of the active substance. For FS - type compositions, add up to 40% by weight of a binder (such as polyvinyl alcohol).

[0511] vi) Water - dispersible granules and water - soluble granules (WG, SG)

[0512] Finely grind 50 - 80% by weight of the diamino - triazine compound of formula (I) of the present invention in the presence of a dispersant and wetting agent (such as sodium lignosulfonate and alcohol ethoxylate) up to 100% by weight and make it into water - dispersible or water - soluble granules with the aid of an industrial device (such as an extruder, spray tower, fluidized bed). Dilute with water to obtain a stable dispersion or solution of the active substance.

[0513] vii) Water - dispersible powders and water - soluble powders (WP, SP, WS)

[0514] Grind 50 - 80% by weight of the diamino - triazine compound of formula (I) of the present invention in a rotor - stator mill in the presence of 1 - 5% by weight of a dispersant (such as sodium lignosulfonate), 1 - 3% by weight of a wetting agent (such as alcohol ethoxylate) and a solid carrier (such as silica gel) up to 100% by weight. Dilute with water to obtain a stable dispersion or solution of the active substance.

[0515] viii) Gels (GW, GF)

[0516] In a stirred ball mill, comminute 5 - 25% by weight of the diamino - triazine compound of formula (I) of the present invention in the presence of 3 - 10% by weight of a dispersant (such as sodium lignosulfonate), 1 - 5% by weight of a thickener (such as carboxymethyl cellulose) and water up to 100% by weight to obtain a fine suspension of the active substance. Dilute with water to obtain a stable suspension of the active substance.

[0517] iv) Microemulsions (ME)

[0518] 5-20% by weight of the diaminotriazine compound of formula (I) according to the invention is added to a 5-30% by weight organic solvent blend (such as fatty acid dimethylamide and cyclohexanone), a 10-25% by weight surfactant blend (such as alcohol ethoxylate and arylphenol ethoxylate), and water up to 100% by weight. The mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0519] iv) Microcapsules (CS)

[0520] An oil phase comprising 5-50% by weight of the diaminotriazine compound of formula (I) according to the invention, 0-40% by weight of a water-insoluble organic solvent (such as aromatic hydrocarbons), and 2-278% by weight of an acrylic monomer (such as methyl methacrylate, methacrylic acid, and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (such as polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50% by weight of the diaminotriazine compound of formula (I) according to the invention, 0-40% by weight of a water-insoluble organic solvent (such as aromatic hydrocarbons), and an isocyanate monomer (such as diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (such as polyvinyl alcohol). The addition of a polyamine (such as hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1-10% by weight. % by weight relates to the entire CS composition.

[0521] ix) Dustable powders (DP, DS)

[0522] 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 (such as finely ground kaolin) up to 100% by weight.

[0523] x) Granules (GR, FG)

[0524] 0.5-30% by weight of the diaminotriazine compound of formula (I) according to the invention is finely ground and combined with a solid carrier (such as silicate) up to 100% by weight. Granulation is achieved by extrusion, spray drying, or fluidized bed.

[0525] xi) Ultra-low volume liquids (UL)

[0526] 1-50% by weight of the diaminotriazine compound of formula (I) according to the invention is dissolved in an organic solvent (such as aromatic hydrocarbons) up to 100% by weight.

[0527] The agrochemical compositions of types i)-xi) may optionally contain other auxiliaries, such as 0.1-1% by weight of a fungicide, 5-278% by weight of an antifreeze, 0.1-1% by weight of an antifoaming agent, and 0.1-1% by weight of a colorant.

[0528] Agrochemical compositions generally contain 0.01 - 95% by weight, preferably 0.1 - 90% by weight, especially 0.5 - 75% by weight of the diaminotriazine compound of formula (I). The diaminotriazine compound of formula (I) is used in a purity of 90 - 100%, preferably 95 - 100% (according to NMR spectroscopy).

[0529] For treating plant propagation materials, especially seeds, solutions for seed treatment (LS), suspension emulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water - dispersible powders for slurry treatment (WS), water - soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are generally used. The agrochemical composition gives an active substance concentration of 0.01 - 60% by weight, preferably 0.1 - 40% by weight in the ready - to - use preparation after dilution 2 - 10 times. Application can be carried out before or during sowing.

[0530] The method of applying the diaminotriazine compound of formula (I) or its agrochemical composition to plant propagation materials, especially seeds, includes methods such as dressing, coating, granulating, dusting, soaking and in - furrow application of the propagation materials. Preferably, the compound I or its composition is applied to the plant propagation materials separately by methods that do not induce germination, such as by dressing, granulating, coating and dusting.

[0531] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other pesticides (such as herbicides, insecticides, fungicides, growth regulators, safeners) can be added to the diaminotriazine compound of formula (I) or the agrochemical composition containing them as a premix or, if appropriate, immediately before use (tank mixing). These reagents can be mixed with the agrochemical composition of the present invention in a weight ratio of 1:100 - 100:1, preferably 1:10 - 10:1.

[0532] Users generally use the diaminotriazine compound of formula (I) of the present invention or the agrochemical composition containing them in pre - dosing devices, knapsack sprayers, spray tanks, spray planes or irrigation systems. The agrochemical composition is generally formulated with water, buffer agents and / or other auxiliaries to the required application concentration, thereby obtaining a ready - to - use spray liquid or the agrochemical composition of the present invention. Usually 20 - 2000 liters, preferably 50 - 400 liters of the ready - to - use spray liquid are applied per hectare of agricultural use area.

[0533] According to one embodiment, the user can mix the components of the agrochemical composition of the present invention or partially premixed components, such as components containing the triazines of formula (I) in a spray tank and, if appropriate, other auxiliaries and additives can be added.

[0534] In another embodiment, the user may mix the components of the agrochemical composition of the invention in a spray can by himself, such as the parts of a kit or the parts of a binary or ternary mixture, and, if appropriate, other adjuvants may be added.

[0535] In another embodiment, the components of the agrochemical composition of the invention or partially premixed components may be applied jointly (e.g., after tank mixing) or sequentially, such as the components containing the diaminotriazine compound of formula (I).

[0536] The diaminotriazine compounds of formula (I) are suitable as herbicides. They are suitable for direct use or as a suitably formulated composition (agrochemical composition).

[0537] The diaminotriazine compounds of formula (I) or the agrochemical compositions containing the triazines of formula (I) are very effective in controlling the growth of plants in non-crop areas, especially at high application rates. They act on broad-leaved weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crops. This effect is mainly observed at low application rates.

[0538] The diaminotriazine compounds of formula (I) or the agrochemical compositions containing them are mainly applied to plants by spraying the leaves or to the soil in which the plant seeds have been sown. Here, for example, water can be used as a carrier and applied by conventional spraying techniques with a spray liquid volume of about 100 - 1000 l / ha (e.g., 300 - 400 l / ha). The diaminotriazine compounds of formula (I) or the agrochemical compositions containing them can also be applied by low-volume or ultra-low-volume methods or in the form of microgranules.

[0539] The application of the diaminotriazine compounds of formula (I) or the agrochemical compositions containing them can be carried out before, during and / or after the emergence of unwanted plants.

[0540] The diaminotriazine compounds of formula (I) or the agrochemical compositions containing them can be applied pre-emergence, post-emergence or pre-planting, or together with the seeds of the crop. The diaminotriazine compounds of formula (I) or the agrochemical compositions containing them can also be applied by applying the seeds of the crop pretreated with the diaminotriazine compounds of formula (I) or the agrochemical compositions containing them. If the active ingredient is not well tolerated by certain crops, an application technique (post-directed, last tillage procedure) can be used in which the herbicidal composition is sprayed with a spraying device so that they do not come into contact with the leaves of the sensitive crops as much as possible, while the active ingredient reaches the leaves of the unwanted plants growing below or the bare soil surface.

[0541] In another embodiment, the diamino-triazine compounds of formula (I) or agrochemical compositions comprising them can be applied by treating seeds. The treatment of seeds basically includes all procedures well-known to those skilled in the art based on the diamino-triazine compounds of formula (I) or agrochemical compositions prepared therefrom (seed dressing, seed coating, seed dusting, seed soaking, seed encapsulation, seed multi-layer coating, seed hulling, seed dripping and seed granulation). At this time, the herbicidal composition can be applied diluted or undiluted.

[0542] The term "seed" includes all types of seeds such as maize, seeds, fruits, tubers, seedlings and similar forms. Here, the term seed preferably describes maize and seeds. The seeds used can be seeds of the above useful plants, but can also be seeds of transgenic plants or plants obtained by conventional breeding methods.

[0543] When used in plant protection, the application rate of the active substance without formulation aids, i.e., the diamino-triazine compounds of formula (I), depends on the type of desired effect and is 0.001 - 2 kg / ha, preferably 0.005 - 2 kg / ha, more preferably 0.005 - 0.9 kg / ha, especially 0.05 - 0.5 kg / ha.

[0544] In another embodiment of the present invention, the application rate of the diamino-triazine compounds of formula (I) is 0.001 - 3 kg / ha, preferably 0.005 - 2.5 kg / ha of active substance (a.s.).

[0545] In another preferred embodiment of the present invention, the application rate (total amount of the diamino-triazine compounds of formula (I)) of the diamino-triazine compounds of formula (I) of the present invention depends on the control target, season, target plant and growth stage and is 0.1 - 3000 g / ha, preferably 10 - 1000 g / ha.

[0546] In another preferred embodiment of the present invention, the application rate of the diamino-triazine compounds of formula (I) is 0.1 - 5000 g / ha, preferably 1 - 2500 g / ha or 5 - 2000 g / ha.

[0547] In another preferred embodiment of the present invention, the application rate of the diamino-triazine compounds of formula (I) is 0.1 - 1000 g / ha, preferably 1 - 750 g / ha, more preferably 5 - 500 g / ha.

[0548] In the treatment of plant propagation materials such as seeds, for example, by dusting, coating or soaking the seeds, the usually required amount of active substance is 0.1 - 1000 g, preferably 1 - 1000 g, more preferably 1 - 100 g, most preferably 5 - 100 g / 100 kg of plant propagation material (preferably seeds).

[0549] In another embodiment of the present invention, for treating seeds, the application rate of the active substance, i.e., the diaminotriazine compound of formula (I), is generally 0.001 - 10 kg / 100 kg of seeds.

[0550] When used for protecting materials or stored products, the application rate of the active substance depends on the type of the application area and the desired effect. The amount generally applied in material protection is 0.001 g - 2 kg, preferably 0.005 g - 1 kg of active substance per cubic meter of the treated material.

[0551] Depending on the application method, the diamino triazine compounds of formula (I) or agrochemical compositions containing them can additionally be used on many other crop plants to eliminate unwanted plants. Examples of suitable crop plants are as follows: onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), oat (Avena sativa), sugar beet (Beta vulgaris spec. altissima), fodder beet (Beta vulgaris spec. rapa), oilseed rape (Brassica napus var. napus), swede (Brassica napus var. napobrassica), turnip (Brassica rapa var. silvestris), kale (Brassica oleracea), black mustard (Brassica nigra), tea (Camellia sinensis), safflower (Carthamus tinctorius), pecan (Carya illinoinensis), lemon (Citrus limon), sweet orange (Citrus sinensis), coffee (Coffea arabica) (Coffea canephora, Coffea liberica), cucumber (Cucumis sativus), Bermuda grass (Cynodon dactylon), carrot (Daucus carota), oil palm (Elaeis guineensis), wild strawberry (Fragaria vesca), soybean (Glycine max), upland cotton (Gossypium hirsutum) (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), sunflower (Helianthus annuus), Hevea brasiliensis, barley (Hordeum vulgare), hop (Humulus lupulus), sweet potato (Ipomoea batatas), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), genus 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, 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.

[0552] Preferred crops are groundnut (Arachis hypogaea), sugar beet (Beta vulgaris spec. altissima), oilseed rape (Brassica napus var. napus), kale (Brassica oleracea), lemon (Citrus limon), sweet orange (Citrus sinensis), coffee (Coffea arabica) (Coffea canephora, Coffea liberica), Bermuda grass (Cynodon dactylon), soybean (Glycine max), upland cotton (Gossypium hirsutum) (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), sunflower (Helianthus annuus), barley (Hordeum vulgare), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), apple (Malus spec.), alfalfa (Medicago sativa), tobacco (Nicotiana tabacum) (Nicotiana rustica), olive (Olea europaea), rice (Oryza sativa), lima bean (Phaseolus lunatus), kidney bean (Phaseolus vulgaris), pistachio (Pistacia vera), Pisum sativum, almond (Prunus dulcis), sugar cane (Saccharum officinarum), rye (Secale cereale), potato (Solanum tuberosum), sorghum (Sorghum bicolor) (Sorghum vulgare), triticale, common wheat (Triticum aestivum), durum wheat (Triticum durum), broad bean (Vicia faba), grapevine (Vitis vinifera) and maize (Zea mays).

[0553] Particularly preferred crops are cereal crops, maize, soybean, rice, oilseed rape, cotton, potato, groundnut or perennial crops.

[0554] The diamino triazine compounds of formula (I) according to the invention or agrochemical compositions comprising them can also be used in genetically modified plants. The term "genetically modified plant" should be understood to mean a plant whose genetic material has been modified by using recombinant DNA techniques to include an inserted sequence of DNA that is not native to the genome of the plant variety or to exhibit a deletion of DNA that is native to the genome of the variety, where the modification cannot be obtained by crossing, mutation or natural recombination alone. Particular genetically modified plants are usually plants that have obtained their genetic modification by inheritance from a progenitor plant whose genome has been directly treated by using recombinant DNA techniques, by natural breeding or propagation methods. One or more genes are usually integrated into the genetic material of the genetically modified plant to improve certain properties of the plant. Such genetic modifications also include, but are not limited to, targeted post-translational modifications of proteins, oligopeptides or polypeptides, for example by amino acid mutations that allow, reduce or promote glycosylation or polymer addition such as isoprenylation, acetylation or farnesylation or the attachment of a PEG moiety.

[0555] Plants modified by breeding, mutagenesis or genetic engineering are, for example, tolerant to the application of special classes of herbicides as a result of conventional breeding or genetic engineering methods. These herbicides include auxin herbicides such as dicamba or 2,4-D; bleaching herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonylureas or imidazolinones; enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl-CoA carboxylase (ACCase) inhibitors; or oxynil (i.e., bromoxynil or ioxynil) herbicides. In addition, plants have been modified by multiple genetic modifications to be tolerant to multiple classes of herbicides, such as tolerant to both glyphosate and glufosinate or tolerant to both glyphosate and another class of herbicide selected from ALS inhibitors, HPPD inhibitors, auxin inhibitors or ACCase inhibitors. These herbicide tolerance technologies are described, for example, 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 references cited therein. Several cultivated plants have been made herbicide tolerant by means of gene mutations and conventional breeding methods, such as tolerant to imidazolinones such as imazamox of summer-sown canola (Canola, BASF SE, Germany) or tolerant to sulfonylureas such as tribenuron of sunflower (DuPont, USA). Genetic engineering methods have been used to confer herbicide tolerance to cultivated plants such as soybean, cotton, maize, sugar beet and canola to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are under development or are available under trade names or trademarks (tolerant to glyphosate, Monsanto, U.S.A.), (tolerant to imidazolinones, BASF SE, Germany) and (tolerant to glufosinate, Bayer CropScience, Germany) commercially available.

[0556] In addition, it also includes plants that are capable of synthesizing one or more insecticidal proteins by using recombinant DNA technology, in particular those known from bacteria of the genus Bacillus, especially Bacillus thuringiensis, such as δ-endotoxins, for example CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), for example VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of nematode-settling bacteria, for example Photorhabdus or Xenorhabdus; toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins or other insect-specific neurotoxins; toxins produced by fungi, for example Streptomycetes toxins; plant lectins, for example pea or barley lectins; lectins; protease inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cysteine protease inhibitors or papain inhibitors; ribosome-inactivating proteins (RIP), for example ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolic enzymes, for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitor or HMG-CoA reductase; ion channel blockers, for example sodium channel or calcium channel blockers; juvenile hormone esterase; diuretic hormone receptor (helicokinin receptor); stilbene synthase, bibenzyl synthase, chitinase or glucanase. In the context of the present invention, these insecticidal proteins or toxins are also specifically understood to include pro-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by novel combinations of protein domains (for example see WO 02 / 0278701). Other examples of such toxins or genetically modified plants capable of synthesizing these toxins are disclosed 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. The methods for producing these genetically modified plants are known to the person skilled in the art and are disclosed, for example, in the above-mentioned publications. These insecticidal proteins contained in the genetically modified plants confer on the plants producing these proteins tolerance to pests that are taxonomically arthropods, in particular beetles (Coleoptera), dipteran insects (Diptera) and moths (Lepidoptera) as well as nematodes (Nematoda).Genetically modified plants capable of synthesizing one or more insecticidal proteins are described, for example, in the above-mentioned publications, some of which are commercially available, for example. (Maize variety producing the toxin Cry1Ab) Plus (maize variety producing the toxins Cry1Ab and Cry3Bb1) (Maize variety producing the toxin Cry9c) RW (maize variety producing the toxins Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); 33B (cotton variety producing the toxin Cry1Ac) I (cotton variety producing the toxin Cry1Ac) II (cotton variety producing the toxins Cry1Ac and Cry2Ab2); (Cotton variety producing the VIP toxin); (Potato variety producing the toxin Cry3A); Bt11 (for example CB) and Bt176 from Syngenta Seeds SAS, France (maize variety producing the toxins Cry1Ab and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (maize variety producing a modified version of the toxin Cry3A, see WO03 / 018810), MON 863 from Monsanto Europe S.A., Belgium (maize variety producing the toxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., Belgium (modified version of cotton variety producing the toxin Cry1Ac) and 27807 from Pioneer Overseas Corporation, Belgium (maize variety producing the toxins Cry1F and PAT enzyme).

[0557] In addition, the invention also encompasses plants which, by using recombinant DNA technology, are capable of synthesizing one or more proteins with enhanced resistance or tolerance 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 varieties expressing resistance genes active against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum), or T4 lysozyme (for example potato varieties capable of synthesizing these proteins with enhanced resistance to bacteria such as Erwinia amylovora). Methods for producing these genetically modified plants are known to the person skilled in the art and are described, for example, in the abovementioned publications.

[0558] In addition, the invention also encompasses plants which, by using recombinant DNA technology, are capable of synthesizing one or more proteins to increase yields (such as biomass production, grain yield, starch content, oil content or protein content), tolerance to drought, salt or other growth-limiting environmental factors or tolerance to pests as well as fungal, bacterial and viral pathogens.

[0559] In addition, the invention also encompasses plants which, by using recombinant DNA technology, contain altered amounts or new amounts of constituents to particularly improve human or animal nutrition, for example oil crops which produce health-promoting long-chain ω-3 fatty acids or unsaturated ω-9 fatty acids (such as rape, DOW Agro Sciences, Canada).

[0560] In addition, the invention also encompasses plants which, by using recombinant DNA technology, contain altered amounts or new amounts of constituents to particularly improve raw material production, for example potatoes which produce increased amounts of amylopectin (such as potatoes, BASF SE, Germany).

[0561] Another embodiment of the invention is a method for controlling unwanted plant growth, which comprises allowing at least one compound of formula (I) as defined above in herbicidally active amounts to act on the plants, their environment or their seeds.

[0562] The preparation of the diaminotriazine compounds of formula (I) is illustrated by the examples; however, the subject matter of the invention is not limited to the examples given.

[0563] The products shown below are characterized by the mass ([m / z]) or the retention time (RT; [min.]) determined by HPLC-MS spectrometry.

[0564] HPLC-MS = high performance liquid chromatography coupled to mass spectrometry; HPLC column:

[0565] RP-18 column (Chromolith Speed ROD, obtained from Merck KgaA, Germany), 50 * 4.6 mm; mobile phase: acetonitrile + 0.1% trifluoroacetic acid (TFA) / water + 0.1% TFA at 40 °C for 5 minutes, using a gradient of 5:95 to 100:0, flow rate 1.8 ml / min.

[0566] MS: Quadrupole electrospray ionization, 80 V (positive mode).

[0567] The following abbreviations are used:

[0568] TFA: Trifluoroacetic acid

[0569] CH: Cyclohexane

[0570] EtOAc: Ethyl acetate

[0571] THF: Tetrahydrofuran

[0572] MeOH: Methanol

[0573] HPLC: High performance liquid chromatography

[0574] LC: Liquid chromatography

[0575] MS: Mass spectrometry

[0576] A preparation example

[0577] Example 1: N4-(2-Benzyloxy-6-fluoro-phenyl)-6-(1-methoxy-1-methyl-ethyl)-1,3,5-triazine-2,4-diamine

[0578] Step 1: 1-Benzyloxy-3-fluoro-2-nitrobenzene

[0579]

[0580] K2CO3 (25.3 g, 183 mmol, 1.2 eq) was added to a 100 ml DMF solution of 3-fluoro-2-nitro-phenol (24.0 g, 153 mmol, 1.0 eq). At room temperature, benzyl bromide (26.1 g, 153 mmol, 1.0 eq) was added to the suspension. The mixture was stirred overnight for 18 hours. Water was added to the reaction mixture to dissolve any salts. The solution was extracted three times with 100 ml of EtOAc. The combined organic layers were washed with water, dried over Na2SO4, and then evaporated. The solid residue was used in the next step without further purification.

[0581] LC / MS RT: 1.204. LC / MS (m / z): No ionization of the molecule was observed

[0582] 1 H-NMR(400MHz, CDCl3) δ 5.2(s, 2H), 6.8–6.9(m, 2H), 7.3–7.4(m, 6H)

[0583] Step 2: 2-Benzyloxy-6-fluoro-aniline

[0584]

[0585] Suspend zinc powder (52.9 g, 809 mmol, 4.0 eq) in 400 ml of acetic acid. Slowly add 1-benzyloxy-3-fluoro-2-nitro-benzene (50 g, 202 mmol, 1.0 eq) dissolved in 80 ml of EtOAc such that the temperature of the reaction mixture does not exceed 40 °C. Stir the mixture at ambient temperature over the weekend and then dilute with 300 ml of EtOAc. After filtration, add water. Wash the organic layer with saturated NaHCO3 solution and then evaporate. Purify the crude product by column chromatography (silica gel, cyclohexane / EtOAc) to give the desired product (29.7 g, 67% yield), as a pale yellow oil.

[0586] LC / MS RT: 1.051. LC / MS (m / z): 217.9 [M+H +

[0587] 1 H-NMR(400MHz, CDCl3) δ 3.2–4.1(br, 2H), 5.08(s, 2H), 6.55–6.75(m, 3H), 7.3–7.5(m, 5H)

[0588] Step 3: 4-(1-Methoxy-1-methyl-ethyl)-6-methylthio-1,3,5-triazin-2-amine

[0589]

[0590] Dissolve 2-methoxy-2-methyl-propanoic acid (5.4 g, 45.7 mmol, 1.01 eq) in 10 ml of CH2Cl2. After adding 3 drops of DMF, add oxalyl chloride (5.8 g, 45.7 mmol, 1.01 eq) at ambient temperature. After 1 hour, when no more gas evolution is observed, slowly add this solution to a solution of 1-formamidinium-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 di ane. After stirring at 60 °C for 4 hours, add water and EtOAc. Separate the organic phase, dry over Na2SO4 and evaporate to give 9.4 g of a crude product, which is used in the next step without further purification.​

[0591] LC / MS RT: 0.742. LC / MS (m / z): 215.1 [M+H +

[0592] 1 H-NMR (400 MHz, DMSO-d6) δ 1.41 (d, 6H), 2.44 (s, 3H), 3.05 (s, 3H), 7.53 (d, 2H)

[0593] Step 4: 4-Chloro-6-(1-methoxy-1-methylethyl)-1,3,5-triazin-2-amine

[0594]

[0595] Chlorine gas was introduced into a solution of 4-(1-methoxy-1-methylethyl)-6-methylthio-1,3,5-triazin-2-amine (9.4 g, 43.9 mmol, 1.0 eq) in 100 ml of EtOAc / CHCl3 for 30 minutes at ambient temperature. Due to incomplete conversion of the starting material, chlorine gas was introduced for an additional 30 minutes. Thereafter, the solution was purged with N2 gas and concentrated. The solid residue was treated with water, the precipitated solid was filtered and dried to give 5.7 g of a crude product, which was used in the next step.

[0596] 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)

[0597] 1 H-NMR (400 MHz, DMSO-d6) δ

[0598] Step 5: N4-(2-Benzyloxy-6-fluorophenyl)-6-(1-methoxy-1-methylethyl)-1,3,5-triazine-2,4-diamine

[0599]

[0600] 2-Benzyloxy-6-fluoroaniline (400 mg, 1.8 mmol, 1.0 eq) and 4-chloro-6-(1-methoxy-1-methylethyl)-1,3,5-triazin-2-amine (373 mg, 1.8 mmol, 1.0 eq) were suspended in 5 ml of di ane. Hydrochloric acid in di ​Alkane solution (4.1 ml, 4.0 molar solution, 3.0 eq), 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 Na2SO4, evaporated to give the crude product, which was purified by column chromatography (silica gel, cyclohexane / EtOAc) to give the desired product (163 mg, 23% yield).

[0601] LC / MS RT: 0.921. LC / MS (m / z): 384.0 [M+H +

[0602] 1 1H-NMR (400 MHz, DMSO-d6) 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)

[0603] Example 2: N4-(2-Benzyloxy-6-fluoro-phenyl)-6-(1-fluoro-2-methyl-propyl)-1,3,5-triazine-2,4-diamine

[0604] Step 1: 1-(2-Benzyloxy-6-fluoro-phenyl)-3-formamidinoguanidine hydrochloride

[0605]

[0606] 2-Benzyloxy-6-fluoro-aniline (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 give 23.7 g of the HCl salt. The free base could be obtained by treating with sodium hydroxide solution and extracting the aqueous mixture with EtOAc.

[0607] LC / MS RT: 0.761. LC / MS (m / z): 301.9 [M+H +

[0608] Step 2: N4-(2-Benzyloxy-6-fluoro-phenyl)-6-(1-fluoro-2-methyl-propyl)-1,3,5-triazine-2,4-diamine

[0609]

[0610] ​​Dissolve 2-fluoro-3-methyl-butyric acid (1.1 g, 9.31 mmol, 1.0 eq) in 30 ml of CH2Cl2. Slowly add DAST (3.0 g, 18.6 mmol, 2.0 eq) at -78 °C. After self-heating to ambient temperature overnight, add the mixture to a solution of 1-(2-benzyloxy-6-fluoro-phenyl)-3-formamido-guanidine and triethylamine in 60 ml of diethane. Stir the reaction mixture at 50 °C for 3 hours. After cooling to ambient temperature, pour the mixture into water and extract with additional CH2Cl2. After evaporating the solvent, the crude product is purified by column chromatography (silica gel, cyclohexane / EtOAc) to give the desired product (45 mg, 1.3% yield) as a white solid.

[0611] LC / MS RT: 1.061. LC / MS (m / z): 385.9 [M+H +

[0612] 1 1H-NMR (500 MHz, DMSO-d6) 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, 10H), 8.75 (b, 1H)

[0613] Prepare the compounds listed in Table 2 below (Examples 3 - 263) in a similar manner to the above example:

[0614]

[0615]

[0616]

[0617]

[0618]

[0619]

[0620]

[0621]

[0622]

[0623]

[0624]

[0625] B Application Examples ​

[0626] The herbicidal activity of the quinolines of the formula (I) was confirmed by the following greenhouse tests:

[0627] The cultivation containers used were plastic flower pots containing loamy sand with approximately 3.0% humus as the substrate. The seeds of the test plants were sown separately for each variety.

[0628] For pre - emergence treatment, the active ingredient, suspended or emulsified in water, was applied directly after sowing with a fine distribution nozzle. The containers were gently irrigated to promote germination and growth and then covered with a transparent plastic hood until the plants had rooted. This covering led to uniform germination of the test plants, unless this was impaired by the active ingredient.

[0629] For post - emergence treatment, the test plants were first grown to a height of 3 - 15 cm, depending on the plant habit, and only then treated with the active ingredient suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or were first grown separately as seedlings and transplanted into the test containers a few days before treatment.

[0630] Depending on the variety, the plants were kept at 10 - 25 °C or 20 - 35 °C.

[0631] The test period was 2 - 4 weeks. During this period, the plants were tended and their response to each treatment was evaluated.

[0632] The evaluation was carried out using a scale of 0 - 100. 100 means that no plants emerged, or at least the above - ground parts were completely damaged, while 0 means no damage or normal growth. A score of at least 60 was given for moderate herbicidal activity, at least 70 for good herbicidal activity, and at least 85 for very good herbicidal activity.

[0633] The plants used in the greenhouse tests were of the following varieties:

[0634]

[0635]

[0636] Example 4, applied at an application rate of 250 g / ha by the pre - emergence method, showed 100% herbicidal activity against *Alopecurus myosuroides*, *Amaranthus retroflexus*, *Echinochloa crus - galli* and *Setaria faberi*.

[0637] Example 5, applied at an application rate of 250 g / ha by the pre - emergence method, showed 85%, 98%, 100% and 98% herbicidal activity against *Alopecurus myosuroides*, *Amaranthus retroflexus*, *Echinochloa crus - galli* and *Setaria faberi*, respectively.

[0638] Example 6, applied at an application rate of 250 g / ha by the pre - emergence method, showed 100% herbicidal activity against *Amaranthus retroflexus*, *Echinochloa crus - galli* and *Setaria faberi*.

[0639] Example 9 applied at a rate of 250 g / ha by the pre-emergence method showed 80%, 95%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0640] Example 10 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0641] Example 11 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0642] Example 14 applied at a rate of 250 g / ha by the pre-emergence method showed 85%, 90% and 80% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0643] Example 18 applied at a rate of 250 g / ha by the pre-emergence method showed 70%, 70%, 70% and 85% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0644] Example 19 applied at a rate of 250 g / ha by the pre-emergence method showed 70%, 80% and 85% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus and Setaria faberi, respectively.

[0645] Example 20 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 98%, 100% and 95% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0646] Example 22 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0647] Example 23 applied at a rate of 250 g / ha by the pre-emergence method showed 100% and 75% herbicidal activity against Echinochloa crus-galli and Setaria faberi, respectively.

[0648] Example 26 applied at a rate of 250 g / ha by the pre-emergence method showed 85%, 80% and 70% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi, respectively.

[0649] Example 27 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi.

[0650] Example 28 applied at a rate of 125 g / ha by the post-emergence method showed 75%, 85% and 75% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria viridis, respectively.

[0651] Example 30 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0652] Example 31 applied at a rate of 250 g / ha by the pre-emergence method showed 85%, 75% and 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus-galli, respectively.

[0653] Example 33 applied at a rate of 250 g / ha by the pre-emergence method showed 75% and 60% herbicidal activity against Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0654] Example 35 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0655] Example 36 applied at a rate of 250 g / ha by the pre-emergence method showed 100% and 75% herbicidal activity against Amaranthus retroflexus and Echinochloa crus-galli, respectively.

[0656] Example 39 applied at a rate of 250 g / ha by the pre-emergence method showed 90%, 80%, 100% and 90% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0657] Example 42 applied at a rate of 250 g / ha by the pre-emergence method showed 100% and 80% herbicidal activity against Amaranthus retroflexus and Abutilon theophrasti, respectively.

[0658] Example 43 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Abutilon theophrasti and Echinochloa crus-galli.

[0659] Example 44 applied at a rate of 250 g / ha by the pre-emergence method showed 70% and 70% herbicidal activity against Setaria faberi and Abutilon theophrasti, respectively.

[0660] Example 45 applied at a rate of 250 g / ha by the pre-emergence method showed 80%, 70% and 80% herbicidal activity against Alopecurus myosuroides, Setaria faberi and Echinochloa crus-galli, respectively.

[0661] Example 47 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 100% and 80% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus-galli, respectively.

[0662] Example 52 applied at a rate of 250 g / ha by the pre-emergence method showed 90% and 85% herbicidal activity against Echinochloa crus-galli and Setaria viridis, respectively.

[0663] Example 54 applied at a rate of 250 g / ha by the pre-emergence method showed 90% and 100% herbicidal activity against Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0664] Example 56 applied at a rate of 250 g / ha by the pre-emergence method showed 100% and 95% herbicidal activity against Lolium multiflorum and Echinochloa crus-galli, respectively.

[0665] Example 58 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 90% and 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria viridis, respectively.

[0666] Example 60 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria viridis, respectively.

[0667] Example 61 applied at a rate of 250 g / ha by the pre-emergence method showed 80%, 100% and 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria viridis, respectively.

[0668] Example 65 applied at a rate of 250 g / ha by the pre-emergence method showed 95% and 95% herbicidal activity against Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0669] Example 69 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria viridis.

[0670] Example 70 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Echinochloa crus-galli.

[0671] Example 72 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria viridis.

[0672] Example 73 applied at a rate of 250 g / ha by the pre-emergence method showed 70% and 75% herbicidal activity against Amaranthus retroflexus and Echinochloa crus-galli, respectively.

[0673] Example 74 applied at a rate of 250 g / ha by the pre-emergence method showed 80% and 85% herbicidal activity against Amaranthus retroflexus and Echinochloa crus-galli, respectively.

[0674] Example 77 applied at a rate of 250 g / ha by the pre-emergence method showed 80%, 100% and 100% herbicidal activity against Abutilon theophrasti, Setaria faberi and Echinochloa crusgalli, respectively.

[0675] Example 78 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 100% and 75% herbicidal activity against Alopecurus myosuroides, Echinochloa crusgalli and Setaria faberi, respectively.

[0676] Example 83 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crusgalli and Setaria faberi.

[0677] Example 85 applied at a rate of 250 g / ha by the pre-emergence method showed 70%, 70% and 90% herbicidal activity against Setaria faberi, Alopecurus myosuroides and Abutilon theophrasti, respectively.

[0678] Example 91 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crusgalli and Setaria faberi.

[0679] Example 94 applied at a rate of 250 g / ha by the pre-emergence method showed 100% and 70% herbicidal activity against Alopecurus myosuroides and Amaranthus retroflexus, respectively.

[0680] Example 96 applied at a rate of 250 g / ha by the pre-emergence method showed 80%, 100%, 100% and 95% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crusgalli and Setaria faberi, respectively.

[0681] Example 97 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crusgalli and Setaria faberi.

[0682] Example 98 applied at a rate of 250 g / ha by the pre-emergence method showed 80%, 90%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crusgalli and Setaria faberi, respectively.

[0683] Example 99 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 100%, 90% and 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crusgalli and Setaria faberi, respectively.

[0684] Example 100 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 100% and 80% herbicidal activity against Amaranthus retroflexus, Echinochloa crusgalli and Abutilon theophrasti, respectively.

[0685] Example 102 applied at an application rate of 250 g / ha by the pre-emergence method showed 100%, 100% and 85% herbicidal activity against Setaria faberi, Echinochloa crus-galli and Abutilon theophrasti, respectively.

[0686] Example 107 applied at an application rate of 250 g / ha by the pre-emergence method showed 75%, 75%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0687] Example 108 applied at an application rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0688] Example 110 applied at an application rate of 250 g / ha by the pre-emergence method showed 90% and 80% herbicidal activity against Echinochloa crus-galli and Setaria faberi, respectively.

[0689] Example 111 applied at an application rate of 250 g / ha by the post-emergence method showed 100% herbicidal activity against Abutilon theophrasti and Amaranthus retroflexus.

[0690] Example 111 applied at an application rate of 250 g / ha by the pre-emergence method showed 80% and 85% herbicidal activity against Axonopus compressus and Echinochloa crus-galli, respectively.

[0691] Example 112 applied at an application rate of 250 g / ha by the post-emergence method showed 100% herbicidal activity against Abutilon theophrasti and Amaranthus retroflexus.

[0692] Example 112 applied at an application rate of 250 g / ha by the pre-emergence method showed 80% herbicidal activity against Axonopus compressus and Echinochloa crus-galli.

[0693] Example 114 applied at an application rate of 250 g / ha by the pre-emergence method showed 90% herbicidal activity against Echinochloa crus-galli and Setaria faberi.

[0694] Example 116 applied at an application rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0695] Example 117 applied at an application rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0696] Example 120 applied at an application rate of 250 g / ha by the pre-emergence method showed 75%, 100% and 90% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0697] Example 121 applied at a rate of 250 g / ha by the post - emergence method showed 100% herbicidal activity against Abutilon theophrasti and Amaranthus retroflexus.

[0698] Example 121 applied at a rate of 250 g / ha by the pre - emergence method showed 80% herbicidal activity against Amaranthus retroflexus.

[0699] Example 125 applied at a rate of 250 g / ha by the pre - emergence method showed 85% and 100% herbicidal activity against Axonopus compressus and Echinochloa crus - galli, respectively.

[0700] Example 128 applied at a rate of 250 g / ha by the pre - emergence method showed 100%, 90% and 90% herbicidal activity against Amaranthus retroflexus, Setaria faberi and Abutilon theophrasti, respectively.

[0701] Example 129 applied at a rate of 250 g / ha by the pre - emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus - galli and Setaria faberi.

[0702] Example 130 applied at a rate of 250 g / ha by the pre - emergence method showed 100% herbicidal activity against Abutilon theophrasti, Setaria faberi and Echinochloa crus - galli.

[0703] Example 131 applied at a rate of 250 g / ha by the pre - emergence method showed 90%, 85% and 90% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Setaria faberi, respectively.

[0704] Example 132 applied at a rate of 250 g / ha by the pre - emergence method showed 90%, 90% and 100% herbicidal activity against Amaranthus retroflexus, Setaria faberi and Echinochloa crus - galli, respectively.

[0705] Example 134 applied at a rate of 250 g / ha by the pre - emergence method showed 95%, 90% and 90% herbicidal activity against Axonopus compressus, Echinochloa crus - galli and Setaria faberi, respectively.

[0706] Example 135 applied at a rate of 250 g / ha by the pre - emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Setaria faberi and Echinochloa crus - galli.

[0707] Example 136 applied at a rate of 250 g / ha by the pre - emergence method showed 80%, 85% and 80% herbicidal activity against Axonopus compressus, Echinochloa crus - galli and Setaria faberi, respectively.

[0708] Example 139 applied at a rate of 250 g / ha by the pre - emergence method showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, Echinochloa crus - galli and Setaria faberi.

[0709] Example 140 applied at a rate of 250 g / ha by the pre-emergence method showed 98% and 100% herbicidal activity against Echinochloa crus-galli and Setaria viridis, respectively.

[0710] Example 141 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100% and 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria viridis, respectively.

[0711] Example 142 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria viridis.

[0712] Example 143 applied at a rate of 250 g / ha by the pre-emergence method showed 90% and 100% herbicidal activity against Alopecurus myosuroides and Amaranthus retroflexus, respectively.

[0713] Example 148 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria viridis.

[0714] Example 149 applied at a rate of 250 g / ha by the pre-emergence method showed 85%, 90% and 75% herbicidal activity against Alopecurus myosuroides, Setaria viridis and Echinochloa crus-galli, respectively.

[0715] Example 152 applied at a rate of 250 g / ha by the pre-emergence method showed 100% and 90% herbicidal activity against Amaranthus retroflexus and Setaria viridis, respectively.

[0716] Example 154 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria viridis.

[0717] Example 160 applied at a rate of 250 g / ha by the pre-emergence method showed 85% and 75% herbicidal activity against Alopecurus myosuroides and Setaria viridis, respectively.

[0718] Example 161 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Echinochloa crus-galli and Setaria viridis.

[0719] Example 163 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria viridis.

[0720] Example 164 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria viridis.

[0721] Example 165 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides, and Echinochloa crus-galli.

[0722] Example 167 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides, and Setaria faberi.

[0723] Example 169 applied at a rate of 250 g / ha by the pre-emergence method showed 80% and 85% herbicidal activity against Amaranthus retroflexus and Setaria faberi, respectively.

[0724] Example 170 applied at a rate of 250 g / ha by the pre-emergence method showed 90%, 100%, and 90% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli, and Setaria faberi, respectively.

[0725] Example 171 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 85%, and 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli, and Setaria faberi, respectively.

[0726] Example 172 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli, and Setaria faberi.

[0727] Example 173 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, and Echinochloa crus-galli.

[0728] Example 174 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli, and Setaria faberi.

[0729] Example 175 applied at a rate of 250 g / ha by the pre-emergence method showed 85%, 100%, and 95% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli, and Setaria faberi, respectively.

[0730] Example 176 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 100%, and 80% herbicidal activity against Echinochloa crus-galli, Setaria faberi, and Amaranthus retroflexus, respectively.

[0731] Example 177 applied at a rate of 250 g / ha by the pre-emergence method showed 85%, 100%, and 95% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli, and Setaria faberi, respectively.

[0732] Example 178 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100%, and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli, and Setaria faberi, respectively.

[0733] Example 180 applied at a rate of 250 g / ha by the pre-emergence method showed 90%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0734] Example 181 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0735] Example 182 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0736] Example 183 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi.

[0737] Example 184 applied at a rate of 250 g / ha by the pre-emergence method showed 85%, 95% and 98% herbicidal activity against Alopecurus myosuroides, Amaranthus retroflexus and Echinochloa crus-galli, respectively.

[0738] Example 185 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0739] Example 186 applied at a rate of 250 g / ha by the pre-emergence method showed 85% and 98% herbicidal activity against Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0740] Example 187 applied at a rate of 250 g / ha by the pre-emergence method showed 85%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0741] Example 188 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides and Echinochloa crus-galli.

[0742] Example 189 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0743] Example 191 applied at a rate of 250 g / ha by the pre-emergence method showed 95%, 100% and 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0744] Example 192 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Echinochloa crus-galli and Setaria faberi.

[0745] Example 193 applied at a rate of 250 g / ha by the pre-emergence method showed 80%, 95% and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0746] Example 194 applied at a rate of 250 g / ha by the pre-emergence method showed 100% and 70% herbicidal activity against Echinochloa crus-galli and Setaria faberi, respectively.

[0747] Example 196 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100% and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0748] Example 198 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100% and 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi, respectively.

[0749] Example 199 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides and Echinochloa crus-galli.

[0750] Example 200 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi.

[0751] Example 201 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi.

[0752] Example 202 applied at a rate of 250 g / ha by the pre-emergence method showed 80%, 80% and 85% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi, respectively.

[0753] Example 203 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi.

[0754] Example 204 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi.

[0755] Example 205 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi.

[0756] Example 206 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides, Echinochloa crus-galli, and Setaria viridis.

[0757] Example 207 applied at a rate of 250 g / ha by the pre-emergence method showed 90%, 100%, and 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli, and Setaria viridis, respectively.

[0758] Example 208 applied at a rate of 250 g / ha by the pre-emergence method showed 90% and 80% herbicidal activity against Abutilon theophrasti and Amaranthus retroflexus, respectively.

[0759] Example 209 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli, and Setaria viridis.

[0760] Example 210 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli, and Setaria viridis.

[0761] Example 211 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli, and Setaria viridis.

[0762] Example 212 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli, and Setaria viridis.

[0763] Example 213 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli, and Setaria viridis.

[0764] Example 214 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 98%, and 90% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides, and Setaria viridis, respectively.

[0765] Example 215 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 98%, and 98% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli, and Setaria viridis, respectively.

[0766] Example 216 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 98%, and 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides, and Setaria viridis, respectively.

[0767] Example 217 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100%, and 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli, and Setaria viridis, respectively.

[0768] Example 218 applied at a rate of 250 g / ha by the pre-emergence method showed 95%, 85% and 100% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0769] Example 219 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 85% and 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi, respectively.

[0770] Example 220 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 95% and 90% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0771] Example 222 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 100% and 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi, respectively.

[0772] Example 223 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 95% and 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi, respectively.

[0773] Example 224 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 90% and 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi, respectively.

[0774] Example 226 applied at a rate of 250 g / ha by the pre-emergence method showed 90%, 100% and 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0775] Example 227 applied at a rate of 250 g / ha by the pre-emergence method showed 90%, 75% and 85% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0776] Example 228 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 100% and 90% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0777] Example 229 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides and Echinochloa crus-galli.

[0778] Example 230 applied at a rate of 250 g / ha by the pre-emergence method showed 95%, 95% and 95% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0779] Example 231, applied at a rate of 250 g / ha by the pre-emergence method, showed 98%, 98% and 98% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0780] Example 232, applied at a rate of 250 g / ha by the pre-emergence method, showed 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi.

[0781] Example 233, applied at a rate of 250 g / ha by the pre-emergence method, showed 75%, 80% and 95% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0782] Example 234, applied at a rate of 250 g / ha by the pre-emergence method, showed 100%, 90% and 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0783] Example 235, applied at a rate of 250 g / ha by the pre-emergence method, showed 85%, 90% and 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0784] Example 236, applied at a rate of 250 g / ha by the pre-emergence method, showed 100%, 95% and 100% herbicidal activity against Abutilon theophrasti, Alopecurus myosuroides and Echinochloa crus-galli, respectively.

[0785] Example 237, applied at a rate of 250 g / ha by the pre-emergence method, showed 95%, 100% and 95% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0786] Example 238, applied at a rate of 250 g / ha by the pre-emergence method, showed 80%, 98% and 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0787] Example 240, applied at a rate of 250 g / ha by the pre-emergence method, showed 100%, 90% and 95% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0788] Example 241, applied at a rate of 250 g / ha by the pre-emergence method, showed 100%, 85% and 85% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi, respectively.

[0789] Example 243, applied at a rate of 250 g / ha by the pre-emergence method, showed 85%, 85% and 85% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi, respectively.

[0790] Example 244 applied at a rate of 250 g / ha by the pre-emergence method showed 85%, 75% and 75% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Setaria faberi, respectively.

[0791] Example 246 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, and Echinochloa crus-galli.

[0792] Example 247 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0793] Example 248 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, and Echinochloa crus-galli.

[0794] Example 249 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi.

[0795] Example 250 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus, and Echinochloa crus-galli.

[0796] Example 251 applied at a rate of 250 g / ha by the pre-emergence method showed 98%, 95% and 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi, respectively.

[0797] Example 252 applied at a rate of 250 g / ha by the pre-emergence method showed 100%, 95% and 100% herbicidal activity against Abutilon theophrasti, Amaranthus retroflexus and Setaria faberi, respectively.

[0798] Example 254 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi.

[0799] Example 255 applied at a rate of 250 g / ha by the pre-emergence method showed 90%, 95% and 90% herbicidal activity against Alopecurus myosuroides, Echinochloa crus-galli and Setaria faberi, respectively.

[0800] Example 256 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus, Echinochloa crus-galli and Setaria faberi.

[0801] Example 257 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Abutilon theophrasti, Echinochloa crus-galli and Setaria faberi.

[0802] Example 259 applied at a rate of 250 g / ha by the pre-emergence method showed 100% herbicidal activity against Amaranthus retroflexus and Setaria faberi.

Claims

1. Diaminotriazine compounds of formula (I): wherein q is 0, 1, 2 or 3; Q is O; wherein R a selected from halogen, CN, C1-C4 alkyl and C1-C4 alkoxy, wherein the aliphatic moiety of said group is unsubstituted, partially or fully halogenated; R b selected from halogen, CN, C1-C4 alkyl and C1-C4 alkoxy, wherein the aliphatic moiety of said group is unsubstituted, partially or fully halogenated; For q = 2 or 3, where it is possible that R b are the same or different; R 1 selected from H, C1-C6 alkyl; R 2 selected from H, halogen, OH, CN, C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkyl, C3-C6 cycloalkyl, (C3-C6 cycloalkyl)-C1-C4 alkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkoxy, (C3-C6 cycloalkyl)-C1-C4 alkoxy, wherein the aliphatic and cycloaliphatic moieties of said groups are unsubstituted, partially or fully halogenated; R 3 selected from H, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy and C1-C6 haloalkoxy; R 4 selected from halogen, CN, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, (C3-C6 cycloalkyl)-C1-C4 alkyl, C3-C6 cycloalkenyl and C1-C6 alkoxy-C1-C6 alkyl, wherein the aliphatic and cycloaliphatic moieties of said groups are unsubstituted, partially or fully halogenated; or R 3 and R 4 together with the carbon atom to which it is attached form a structural moiety selected from C3-C6 cycloalkyl, C3-C6 cycloalkenyl, 3- to 6-membered saturated or partially unsaturated heterocyclic group; R 5 selected from H, C1-C6 alkyl; R 6 is phenyl, and the phenyl is unsubstituted or bears 1, 2, 3, 4 or 5 groups R 6A , and the group R 6A is selected from halogen, OH, CN, amino, NO2, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, (C1-C6 alkoxy)-C1-C6 alkyl, (C1-C6 alkoxy)-C1-C6 alkoxy, (C1-C6 alkoxy)-C2-C6 alkenyl, (C1-C6 alkoxy)-C2-C6 alkynyl, C1-C6 alkylthio, (C1-C6 alkyl)sulfinyl, (C1-C6 alkyl)sulfonyl, (C1-C6 alkyl)amino, di(C1-C6 alkyl)amino, (C1-C6 alkyl)-carbonyl, (C1-C6 alkoxy)-carbonyl, (C1-C6 alkyl)-carbonyloxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, (C3-C6 cycloalkyl)-C1-C4 alkyl, (C3-C6 cycloalkyl)-C1-C4 alkoxy, wherein the aliphatic and cycloaliphatic moieties of the group are unsubstituted, partially or completely halogenated and wherein the cycloaliphatic moiety of the group may bear 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 hydrogen, halogen, C1-C4 alkyl; including its agrochemically acceptable salts.

2. The compound according to claim 1, wherein R a is fluorine or chlorine.

3. The compound according to claim 1, wherein R b is selected from fluorine, chlorine, bromine or methyl.

4. The compound according to claim 2, wherein R b is selected from fluorine, chlorine, bromine or methyl.

5. A compound according to any one of claims 1 - 4, wherein R 1 is H.

6. A compound according to any one of claims 1 - 4, wherein R 2 selected from hydrogen, fluorine, C1-C4 alkyl, and C1-C4 alkoxy; R 3 selected from hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C6 haloalkoxy; R 4 selected from 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; or R 3 and R 4 together with the carbon atom to which it is attached form a structural moiety selected from C3-C6 cycloalkyl, C3-C6 cycloalkenyl and 3- to 6-membered saturated or partially unsaturated heterocyclic group.

7. A compound according to claim 5, wherein R 2 selected from hydrogen, fluorine, C1-C4 alkyl, and C1-C4 alkoxy; R 3 selected from hydrogen, fluorine, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, and C1-C6 haloalkoxy; R 4 is selected from 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; or R 3 and R 4 together with the carbon atom to which it is attached form a structural moiety selected from C3-C6 cycloalkyl, C3-C6 cycloalkenyl, and 3- to 6-membered saturated or partially unsaturated heterocyclic group.

8. A compound according to any one of claims 1-4, wherein R 5 is H.

9. A compound according to claim 7, wherein R 5 is H.

10. A compound according to any one of claims 1 - 4, wherein, if present, R 6A is selected from halogen, CN, C1 - C4 alkyl, C1 - C4 haloalkyl, C1 - C4 alkoxy, C1 - C4 haloalkoxy and C3 - C6 cycloalkyl.

11. The compound according to claim 9, wherein, if present, R 6A is selected from halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C3-C6 cycloalkyl.

12. An agrochemical composition comprising a herbicidally effective amount of at least one compound as claimed in any one of claims 1 - 11 and at least one inert liquid and / or solid carrier and, if appropriate, at least one surface-active substance.

13. Use of a compound as claimed in any one of claims 1 - 11 as a herbicide or for desiccating / defoliating plants.

Images