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WO2013092244A1 - Herbicidal triazines - Google Patents

Herbicidal triazines Download PDF

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Publication number
WO2013092244A1
WO2013092244A1 PCT/EP2012/074743 EP2012074743W WO2013092244A1 WO 2013092244 A1 WO2013092244 A1 WO 2013092244A1 EP 2012074743 W EP2012074743 W EP 2012074743W WO 2013092244 A1 WO2013092244 A1 WO 2013092244A1
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alkyl
alkoxy
alkylthio
cycloalkyl
formula
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French (fr)
Inventor
Frederick CALO
Matthias Witschel
Ricarda Niggeweg
Trevor William Newton
William Karl Moberg
Tobias SEISER
Liliana Parra Rapado
Raphael Aponte
Frank Stelzer
Andree Van Der Kloet
Thomas Seitz
Johannes Hutzler
Klaus Kreuz
Klaus Grossmann
Andreas Landes
Anja Simon
Richard Roger Evans
Thomas Mietzner
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings

Definitions

  • the present invention relates to trianzines of the general formula I defined below, to a process for their preparation and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation.
  • WO 09/138712 describes structurally similar compounds for which herbicidal action is stated.
  • triazines having improved herbicidal action.
  • triazines which have high herbicidal activity, in particular even at low application rates, and which are sufficiently compatible with crop plants for commercial utilization.
  • R 1 is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, d-Cs-alkoxy, d-Cs-alkoxy-Ci-Cs- alkyl, Ci-Cs-alkylthio, C-i-Cs-alkylthio-C-i-Cs-alkyl, hydroxy-Ci-Cio-alkyl, aminocarbonyl, (Ci-C6-alkyl)aminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C8-alkyl, C3-C6-cycloalkyl-Ci-C8-haloalkyl, C
  • cycloalkyls are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl and C2-C6-haloalkynyl; is halogen, CN, OH, SH , Ci-C 6 -alkoxy, d-Ce-alkylthio, Ci-C 6 -alkoxy-Ci-C 4 - alkoxy, Ci-C6-alkoxy-Ci-C 4 -alkylthio, Ci-C6-alkylthio-Ci-C 4 -alkoxy, C1-C6- alkyltio-Ci-C 4 -alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, d-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - cycloalkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy-Ci-C 4 -alkyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy
  • phenyls are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO2, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkyl and Ci-C 4 -haloalkoxy; independently of one another are hydrogen, halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylsulfonyl, (Ci-C 6 -alkyl)- amino or di(Ci-C6-alkyl)amino; including their agriculturally acceptable salts or, provided that the triazines of formula I have a carboxyl group, their agriculturally acceptable derivatives.
  • R 2 is halogen, CN, OH, SH, Ci-C 6 -alkoxy, d-Ce-alkylthio, Ci-C 6 -alkoxy-Ci-C 4 - alkoxy, Ci-C6-alkoxy-Ci-C 4 -alkylthio, Ci-C6-alkylthio-Ci-C 4 -alkoxy, C1-C6- alkyltio-Ci-C 4 -alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, d-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - cycloalkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy-Ci-C 4 -alkyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy
  • R 3 , R 4 and R 5 independently of one another are hydrogen, halogen, CN, NO2,
  • the present invention also provides the use of triazines of the general formula I as herbicides, i.e. for controlling harmful plants or for desiccation/defoliation of plants.
  • the present invention also provides compositions comprising at least one triazine of the formula I and auxiliaries customary for formulating crop protection agents.
  • the subject of the present invention are agrochemical compositions comprising a herbicidal active amount of at least one triazine of formula I and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substance.
  • a process for the preparation of herbicidal active agrochemical compositions which comprises mixing a herbicidal active amount of at least one triazine of formula I and at least one inert liquid and/or solid carrier and, if desired, at least one surface- active substance is also the subject of the present invention.
  • the present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one triazine of the formula I is allowed to act on plants, their seeds and/or their habitat.
  • Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
  • the invention relates to processes for preparing the triazines of the formula I.
  • triazines of formula I as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
  • triazines of formula I as described herein have one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions according to the invention.
  • triazines of formula I as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4- alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, te
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • Triazines of formula I as described herein having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-C6-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl
  • esters and also as thioesters for example as C1-C10- alkylthio esters.
  • Preferred mono- and di-Ci-C6-alkylamides are the methyl and the dimethylamides.
  • Preferred arylamides are, for example, the anilides and the 2- chloroanilides.
  • Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), meptyl (1 -methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
  • Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
  • An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
  • the organic moieties mentioned in the definition of the variables R 1 to R 5 are - like the term halogen - collective terms for individual enumerations of the individual group members.
  • the term halogen denotes in each case fluorine, chlorine, bromine or iodine.
  • All hydrocarbon chains, i.e. all alkyl, alkenyl, alkynyl, alkoxy and alkylthio chains can be straight-chain or branched, the prefix C n -C m denoting in each case the possible number of carbon atoms in the group.
  • C n -C m denoting in each case the possible number of carbon atoms in the group.
  • Ci-C4-haloalkyl Ci-C4-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoroprop
  • Ci-Cs-haloalkyI Ci-C6-haloalkyl as mentioned above, and also, for example, n- heptyl, n-octyl or positional isomers thereof where one or more hydrogen atoms in these groups are replaced by halogen atoms as aforesaid;
  • C2-C8-alkenyl and also the alkenyl moieties in composite groups C2-C6-alkenyl as mentioned above, and also, for example, n- heptenyl, n-octenyl or positional isomers thereof having one double bond in any position, e.g. 1 -heptenyl, 2-heptenyl, 3-heptenyl, 1 -octenyl, 2-octenyl, 3-octenyl and 4-octenyl;
  • C2-Cio-alkenyl and also the alkenyl moieties in composite groups C2-Cs-alkenyl an mentioned above and also, for example, n-decenyl, n-nonenyl or positional isomers thereof having one double bond in any position;
  • C2-C8-haloalkenyl and also the alkenyl moieties in composite groups C2-C6- haloalkenyl as mentioned above, and also, for example, 3-fluoro-n-heptenyl-1 , 1 ,3,3,- trichloro-n-heptenyl-5 and 1 ,3,5-trichloro-n-octenyl-6;
  • C3-C6-alkynyl for example 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1 ,1 -dimethyl-2-propynyl, 1 - ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2- pentynyl, 1 -methyl-3-pentynyl, 1 -methyl-4-pentyny
  • C2-C8-alkynyl C2-C6-alkynyl as mentioned above, and also, for example, n- heptinyl, n-octinyl or positional isomers thereof having one or two triple bonds in any position, e.g. 1 -heptynyl, 2-heptynyl, 1 -octynyl and 2-octynyl;
  • C2-Cio-alkynyl C2-Cs-alkynyl mentioned above and also, for example, n-decynyl, n-nonynyl or positional isomers thereof having one or two triple bonds in any position;
  • C2-C6-haloalkynyl a C2-C6-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example
  • C2-C8-haloalkynyl C2-C6-haloalkynyl as mentioned above, and also, for example, n-heptynyl, n-octynyl or positional isomers thereof where one or more hydrogen atoms in these groups are replaced by halogen atoms as aforesaid, e.g. 1 -chloro-2-heptynyl and 1 -chloro-2-octynyl;
  • Ci-C4-haloalkoxy a Ci-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,
  • Ci-C6-haloalkoxy a Ci-C4-haloalkoxy as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy,
  • Ci-C6-alkylsulfonyl (Ci-C6-alkyl-S(0)2-) : for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1 -methylethylsulfonyl, butylsulfonyl, 1 -methylpropylsulfonyl, 2-methyl- propylsulfonyl, 1 ,1 -dimethylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2- methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-di- methylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl,
  • a 5-membered heteroaryl having 1 to 4 nitrogen atoms a monocyclic, aromatic cycle having five ring members and which comprises apart from carbon atoms 1 to 4 nitrogen atoms, for example 1 -pyrrolyl, 1 -pyrazolyl, 1 -imidazolyl, 1 ,2,3— triazol— 1— yl, 1 ,2,4-triazol-1-yl, 1 -tetrazolyl.
  • cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C6-haloalkyl; particulary preferred is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cs-alkynyl, Ci- Cs-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, C-i-Cs-alkoxy-C-i-Cs-alkyl, Ci- C6-alkylthio-Ci-C6-alkyl, hydroxy-C-i-Cs-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C6-alkyl, C
  • cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C3-haloalkyl; especially preferred is Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, C-i-Cs-alkoxy-C-i-Cs-alkyl, Ci-C6-alkylthio- Ci-C6-alkyl, hydroxy-C-i-Cs-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C
  • substituents preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C3-haloalkyl; more preferred is Ci-Cio-alkyl, C2-Cio-alkenyl, d-Cs-haloalkyl, C2-C8-haloalkenyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 6 -alkylthio-Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - cycloalkyl-Ci-C6-alkyl or C3-C6-cycloalkyl-Ci-C6-haloalkyl,
  • substituents preferably by one to three, particularly preferred one or two, more preferred by one substituent(s), selected from the group consisting of halogen and Ci-C6-alkyl; most preferred is Ci-Cio-alkyl, C2-Cio-alkenyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C6-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci-C4- alkyl,
  • cycloalkyls are unsubstituted or substituted by one to three substituents, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of Ci-C6-alkyl; preferably is halogen, CN, OH, SH, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxy- Ci-C4-alkoxy, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, Ci-C6-alkylthiocarbonyloxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to four substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci- C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, C1-C6- alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C
  • phenyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy; particularly preferred is halogen, CN, OH , SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, C1-C6- alkoxycarbonyloxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to three
  • substituents particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, C1-C6- alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl or di(Ci-C2-alkyl)amino,
  • phenyls are unsubstituted or substituted by one to five substituents, preferably one to three, particularly preferred one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy or Ci-C4-haloalkyl; especially preferred is halogen, CN, OH, SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, C1-C6- alkoxycarbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to three
  • substituents particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, C1-C6- alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl or di(Ci-C2-alkyl)amino,
  • phenyls are unsubstituted or substituted by one to five, preferably one to three substituents, particularly preferred one or two substituents selected from the group consisting of halogen, CN , NO2, Ci-C4-alkyl, C1-C4- alkoxy or Ci-C3-haloalkyl; more preferred is halogen, CN, OH, SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, a 5- membered heteroaryl having 2 to 4 nitrogen atoms selected from pyrazoles, imidazoles, 1 ,2,4-triazoles or tetrazoles,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to two substituents selected from the group consisting of halogen, CN , NO2, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C1-C6- alkoxycarbonyl,
  • phenyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of NO2 or Ci-C2-alkoxy; most preferred is halogen, CN, OH , SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy,
  • Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy Ci-C6-alkoxycarbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms selected from pyrazoles, imidazoles,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to two substituents selected from the group consisting of CN, NO2, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkylthio and Ci-C6-alkoxycarbonyl, phenoxy or phenyl-Ci-alkoxy,
  • phenyls are unsubstituted or substituted by one to three substituents, particularly preferred one or two substituents selected from the group consisting of NO2 and Ci-alkoxy;
  • R 3 , R 4 and R 5 preferably independently of one another are hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-alkylsulfonyl or di(Ci-C4-alkyl)amino,
  • R 3 , R 4 and R 5 is H, particularly preferred at least one of R 4 and R 5 is H, especially preferred R 5 is H, more preferred R 5 and R 3 or R 5 and
  • R 4 are H, most preferred R 3 , R 4 and R 5 are H; particulary preferred independently of one another are hydrogen, halogen, CN, NO2, Ci-C3-alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkoxy- d-Cs-alkyl or di(Ci-C 3 -alkyl)amino,
  • R 3 , R 4 and R 5 are H, particularly preferred at least one of R 4 and R 5 is H, especially preferred R 5 is H, more preferred R 5 and R 3 or R 5 and R 4 are H, most preferred R 3 , R 4 and R 5 are H; especially preferred independently of one another are hydrogen, halogen, C1-C3- alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy or Ci-C2-alkoxy- C1-C2- alkyl,
  • R 3 , R 4 and R 5 is H, particularly preferred at least one of R 4 and R 5 is H, especially preferred R 5 is H, more preferred R 5 and R 3 or R 5 and R 4 are H, most preferred R 3 , R 4 and R 5 are H; more preferred independently of one another are hydrogen, halogen, Ci-C2-alkyl or Ci-C2-alkoxy,
  • R 3 , R 4 and R 5 is H, particularly preferred at least one of R 4 and R 5 is H, especially preferred R 5 is H, more preferred R 5 and R 3 or R 5 and R 4 are H, most preferred R 3 , R 4 and R 5 are H; most preferred independently of one another are hydrogen, halogen, Ci-C2-alkyl or Ci-C2-alkoxy,
  • R 3 , R 4 and R 5 is H, particularly preferred at least one of R 4 and R 5 is H, especially preferred R 5 is H, more preferred R 5 and R 3 or
  • R 5 and R 4 are H, most preferred R 3 , R 4 and R 5 are H;
  • R 1 is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cs-alkynyl, C-i-Cs-haloalkyl, C2-C8- haloalkenyl, C2-C8-haloalkynyl, C-i-Cs-alkoxy-C-i-Cs-alkyl, Ci-C6-alkylthio-Ci-C6- alkyl, hydroxy-d-Cs-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6- cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3-C6-cycloalkyl-C2- C6-haloalkenyl,
  • cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C6-haloalkyl; is halogen, CN, OH, SH , Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, Ci-C 6 -alkoxy-Ci-C 4 - alkoxy, Ci-C6-alkylthio-Ci-C 4 -alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, C1-C6- alkoxycarbonyloxy, Ci-C6-alkylthiocarbonyloxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to four substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci- C 4 -alkyl, Ci-C6-alkylthio-Ci-C 4 -alkyl, hydroxycarbonyl, C1-C6- alkoxycarbonyl-Ci-C 4 -alkyl, Ci-C6-alkylthiocarbonyl-C
  • phenyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C 4 -alkyl, Ci-C 4 - alkoxy, Ci-C 4 -haloalkyl and Ci-C 4 -haloalkoxy;
  • R 3 , R 4 and R 5 independently of one another are hydrogen, halogen, CN, NO2, C1-C3- alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkoxy-Ci-C3-alkyl or di(Ci-C3-alkyl)amino,
  • R 3 , R 4 and R 5 is H, particularly preferred at least one of R 4 and R 5 is H, especially preferred R 5 is H, more preferred R 5 and R 3 or
  • R 5 and R 4 are H, most preferred R 3 , R 4 and R 5 are H;
  • haloalkenyl C2-C8-haloalkynyl, Ci-C 0 -alkoxy-Ci-C 0 -alkyl, Ci-C6-alkylthio-Ci-C6- alkyl, hydroxy-Ci-C 0 -alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6- cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3-C6-cycloalkyl-C2- C6-haloalkenyl,
  • cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C3-haloalkyl; is halogen, CN, OH, SH, d-Ce-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-Ce- alkylthio-Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxy- carbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to three substituents, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, C1-C6- alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl or di(Ci-C2-alkyl)amino
  • phenyls are unsubstituted or substituted by one to five, preferably one to three substituents, particularly preferred one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-Cs-haloalkyl;
  • R 3 , R 4 and R 5 independently of one another are hydrogen, halogen, Ci-C3-alkyl, Ci- C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy or Ci-C2-alkoxy- Ci-C2-alkyl, with a proviso that at least R 5 is H, more preferred R 5 and R 3 or R 5 and R 4 are H, most preferred R 3 , R 4 and R 5 are H;
  • cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred one or two, more preferred by one substituent(s), selected from the group consisting of halogen and Ci-C6-alkyll; is halogen, CN, OH, SH , d-Ce-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-Ce- alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms selected from pyrazoles, imidazoles, 1 ,2,4-triazoles or tetrazoles,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to two substituents selected from the group consisting of halogen, CN , NO2, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C1-C6- alkoxycarbonyl,
  • phenyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of NO2 or Ci-C2-alkoxy;
  • R 3 , R 4 and R 5 independently of one another are hydrogen, halogen, Ci-C2-alkyl or Ci-C2-alkoxy,
  • R 5 is H, more preferred R 5 and R 3 or R 5 and R 4 are H, most preferred R 3 , R 4 and R 5 are H;
  • R 1 is Ci-Cio-alkyl, C 2 -Cio-alkenyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy-Ci-C 6 -alkyl, Ci-C 4 - alkylthio-Ci-C 4 -alkyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci-C 4 -alkyl,
  • cycloalkyls are unsubstituted or substituted by one to three substituents, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of Ci-C6-alkyl;
  • R 2 is halogen, CN, OH, SH , Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 4 -alkoxy, Ci-C 6 - alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms selected from pyrazoles, imidazoles, 1 ,2,4-triazoles or tetrazoles
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to two substituents selected from the group consisting of CN, NO2, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkylthio and Ci-C6-alkoxycarbonyl, phenoxy or phenyl-Ci-alkoxy,
  • phenyls are unsubstituted or substituted by one to three substituents, particularly preferred one or two substituents selected from the group consisting of NO2 and Ci-alkoxy;
  • R 3 , R 4 and R 5 independently of one another are hydrogen, halogen, Ci-C2-alkyl or Ci-C2-alkoxy;
  • R 5 is H, more preferred R 5 and R 3 or R 5 and R 4 are H, most preferred R 3 , R 4 and R 5 are H;
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C6-alkyl, C3- C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4-cycloalkyl- C2-C6-haloalkenyl
  • cycloalkyls are unsubstituted or substituted by one to five, preferably one to three, particularly preferred one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkenyl and C2-C4- haloalkynyl; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4- alkyl, C3-C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycl
  • cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl and C2-C4-haloalkenyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl; especially preferred C2-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C2-C6-haloalkyl, C3- C6-haloalkenyl, C3-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-
  • cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl and C2-C4-haloalkenyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
  • substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl and C2-C4-haloalkenyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
  • triazines of formula I wherein R 1 is
  • Ci-C6-alkyl C2-C6-alkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl or C3-C6-cycloalkyl-C2-C6-haloalkenyl,
  • cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci- C 4 -alkyl; particularly preferred Ci-C 4 -alkyl, C2-C 4 -alkenyl, Ci-C 4 -haloalkyl, C2-C4- haloalkenyl, Cs-Cs-cycloalkyl, C3-C5-cycloalkyl-Ci-C6-alkyl, C3-C5-cycloalkyl-Ci- C6-haloalkyl, C3-C5-cycloalkyl-C2-C6-alkenyl or C3-C5-cycloalkyl-C
  • C 4 -alkyl especially preferred Ci-C 4 -alkyl, C2-C 4 -alkenyl, Ci-C 4 -haloalkyl, C2-C4- haloalkenyl, C3-C 4 -cycloalkyl, C3-C 4 -cycloalkyl-Ci-C 4 -alkyl, C3-C 4 -cycloalkyl-Ci- C 4 -haloalkyl, C3-C 4 -cycloalkyl-C2-C 4 -alkenyl or C3-C 4 -cycloalkyl-C2-C 4 -haloalkenyl, which cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C 4 -alkyl and Ci-C 4 -haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-
  • cycloalkyls are unsubstituted or substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C 4 -alkyl, especially preferred selected from the group consisting of fluorine and Ci-C 4 -alkyl.
  • substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C 4 -alkyl, especially preferred selected from the group consisting of fluorine and Ci-C 4 -alkyl.
  • triazines of formula I wherein R 1 is
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci- C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3- C6-cycloa I kyl-C2-C6-hal oa I kenyl ,
  • cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci- C 4 -alkyl; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C 4 -alkyl, C3-C6-cycloalkyl-Ci-C 4 -haloalkyl, C3-C6-cycloalkyl-C2-C 4 - alkenyl or C3-C6-cycloalkyl-C2-C 4 -haloalkenyl,
  • cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C 4 -alkyl, especially preferred selected from the group consisting of fluorine and Ci- C 4 -alkyl; especially preferred Ci-C 4 -alkyl, C2-C 4 -alkenyl, Cs-Cs-cycloalkyI, Cs-Cs-cycloalkyl- Ci-C2-alkyl, C3-C5-cycloalkyl-Ci-C 4 -haloalkyl, C3-C5-cycloalkyl-C2-C 4 -alkenyl or C3-C5-cycloa I kyl-C2-C 4 -hal oa I kenyl ,
  • cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C 4 -alkyl and Ci-C 4 -haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C 4 -alkyl, especially preferred selected from the group consisting of fluorine and Ci-C 4 -alkyl; more preferred C2-C 4 -alkyl, C3-C 4 -alkenyl, C3-C 4 -cycloalkyl, C3-C 4 -cycloalkyl-Ci- C2-alkyl, C3-C 4 -cycloalkyl-Ci-C 4 -haloalkyl, C3-C 4 -cycloalkyl-C2-C 4 -alkenyl or C3- C 4 -cycloa I kyl-C2-C 4 -hal oa I keny
  • cycloalkyls are unsubstituted or substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C 4 -alkyl, especially preferred selected from the group consisting of fluorine and Ci-C 4 -alkyl.
  • C2-C6-alkenyl or C3-C6-cycloalkyl which cycloalkyl isunsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; particularly preferred C2-C4-alkenyl or Cs-Cs-cycloalkyl,
  • cycloalkyl is unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci- C 4 -alkyl; especially preferred C3-C4-alkenyl or C3-C4-cycloalkyl,
  • cycloalkyl is unsubstituted or substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and C1-C2- haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl. More preferred C3-C4-alkenyl or C3-C4-cycloalkyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C6-alkyl, C3- C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4-cycloalkyl- C2-C6-haloalkenyl,
  • Ci-C6-alkyl particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4- alkyl, C3-C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4- cycloalkyl-C2-C6-haloalkenyl,
  • cycloalkyls are unsubstituted; especially preferred C2-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C2-C6-haloalkyl, C3- C6-haloalkenyl, C3-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3-C4- cycloalkyl-C2-C4-haloalkenyl ,
  • Ci-C6-alkyl C2-C6-alkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl or C3-C6-cycloalkyl-C2-C6-haloalkenyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci- C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3-
  • Ci-C6-alkyl particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-haloalkyl, C3-C6-cycloalkyl-C2-C4- alkenyl or C3-C6-cycloalkyl-C2-C4-haloalkenyl,
  • Ci-C4-alkyl which cycloalkyls are unsubstituted; especially preferred Ci-C4-alkyl, C2-C4-alkenyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyl- Ci-C2-alkyl, C3-C5-cycloalkyl-Ci-C4-haloalkyl, C3-C5-cycloalkyl-C2-C4-alkenyl or
  • cycloalkyls are unsubstituted; more preferred C2-C4-alkyl, C3-C4-alkenyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci- C2-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3-
  • cycloalkyl which cycloalkyl is unsubstituted; particularly preferred C2-C4-alkenyl or Cs-Cs-cycloalkyl,
  • cycloalkyl which cycloalkyl is unsubstituted; especially preferred C3-C4-alkenyl or C3-C4-cycloalkyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C6-alkyl, C3 C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4-cycloalkyl- C2-C6-haloalkenyl
  • cycloalkyls are substituted by one to five, preferably one to three, particularly preferred one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkenyl and C2-C4-haloalkynyl; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4- alkyl, C3-C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C
  • cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl and C2-C4-haloalkenyl, particularly preferred selected from the group consisting of halogen and Ci C 4 -alkyl; especially preferred C2-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C2-C6-haloalkyl, C C6-haloalkenyl, C3-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl
  • cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl and C2-C4-haloalkenyl, particularly preferred selected from the group consisting of halogen and Ci C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
  • Ci-C6-alkyl C2-C6-alkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl or C3-C6-cycloalkyl-C2-C6-haloalkenyl,
  • cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; particularly preferred Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl, C2-C4- haloalkenyl, Cs-Cs-cycloalkyl, C3-C5-cycloalkyl-Ci-C6-alkyl, C3-C5-cycloalkyl-Ci- C6-haloalkyl, C3-C5-cycloalkyl-C2-C6-alkenyl or C3-C5-cycloalkyl-C2-C6-haloalkenyl,
  • cycloalkyls are substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
  • R 1 is Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci- C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3- C6-cycloa I kyl-C2-C6-hal oa I kenyl ,
  • cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-haloalkyl, C3-C6-cycloalkyl-C2-C4- alkenyl or C3-C6-cycloalkyl-C2-C4-haloalkenyl,
  • cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; especially preferred Ci-C4-alkyl, C2-C4-alkenyl, Cs-Cs-cycloalkyI, Cs-Cs-cycloalkyl- Ci-C2-alkyl, C3-C5-cycloalkyl-Ci-C4-haloalkyl, C3-C5-cycloalkyl-C2-C4-alkenyl or C3-C5-cycloa I kyl-C2-C4-hal oa I kenyl ,
  • cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; more preferred C2-C4-alkyl, C3-C4-alkenyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci- C2-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3- C4-cycloa I kyl-C2-C4-hal oa I kenyl ,
  • cycloalkyls are substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
  • cycloalkyl is substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; particularly preferred C2-C4-alkenyl or Cs-Cs-cycloalkyl,
  • cycloalkyl is substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; especially preferred C3-C4-alkenyl or C3-C4-cycloalkyl,
  • cycloalkyl is substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
  • halogen CN, OH, SH, Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 4 -alkoxy, Ci-C 6 -alkylthio- Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, Ci- C6-alkylthiocarbonyloxy or a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, Ci- C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci- C4-alkyl, NH2, (Ci-C6-alkyl)amino or di(Ci-C6-alkyl)amino,
  • heteroaryl is selected from the group consisting of X 1 to X 9 :
  • R 6 to R 9 independently of one another are hydrogen, halogen, CN, NO2, C1-C6- alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxy- carbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino or di(Ci-C6- alkyl)amino; particularly preferred halogen, OH, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino;
  • heteroaryl is selected from the group consisting of X 2 to X 8 :
  • R 6 to R 9 independently of one another are hydrogen, halogen, CN, NO2, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthio- carbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4- alkyl)amino; especially preferred halogen, OH, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci- C4-alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 2 to 4 nitrogen atom
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino,
  • heteroaryl is selected from the group consisting of X 2 to X 8 :
  • R 6 to R 9 independently of one another are hydrogen, halogen, CN, NO2, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthio- carbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4- alkyl)amino; more preferred halogen, OH, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 3 nitrogen atoms
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino,
  • heteroaryl is selected from the group consisting of X 4 to
  • R 6 to R 9 independently of one another are hydrogen, halogen, CN, NO2, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthio- carbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxyl- carbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino.
  • Ci-C 6 -alkoxy Ci-C 6 -alkoxy-Ci-C 4 -alkoxy, Ci-C 6 -alkylthio- Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, Ci-
  • heteroaryl is selected from the group consisting of X 1 to X 9 as mentioned above, wherein R 6 to R 9 are hydrogen; particularly preferred halogen, OH, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci- C6-alkoxycarbonyl-Ci-C6-alkoxy or a 5-membered heteroaryl having 2 to 4 nitrogen
  • heteroaryl is selected from the group consisting of X 2 to X 8 as mentioned above, wherein R 6 to R 9 are hydrogen; especially preferred halogen, OH , Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci- C4-alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 2 to 4 nitrogen
  • heteroaryl is selected from the group consisting of X 2 to X 8 as mentioned above, wherein R 6 to R 9 are hydrogen; more preferred halogen, OH, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 3 nitrogen atoms,
  • heteroaryl is selected from the group consisting of X 4 to X 7 as mentioned above, wherein R 6 to R 9 are hydrogen.
  • R 6 to R 9 are hydrogen.
  • triazines of formula I wherein R 2 is
  • halogen CN , OH, SH, Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 4 -alkoxy, Ci-C 6 -alkylthio- Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, Ci- C6-alkylthiocarbonyloxy or a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci- C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino, preferably which heteroaryl is selected from the group consisting of X 2 to
  • R 6 to R 9 independently of one another are halogen, CN, N0 2 , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkylthio, C1-C4- alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (C1-C4- alkyl)amino or di(Ci-C4-alkyl)amino; especially preferred halogen, OH, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci- C4-alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered hetero
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci- C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2,
  • heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (C1-C4- alkyl)amino or di(Ci-C4-alkyl)amino, preferably which heteroaryl is selected from the group consisting of X 4 to X 7 as mentioned above, wherein where the arrow indicates the point of attachment and wherein R 6 to R 9 independently of one another are halogen, CN, N0 2 ,
  • R 3 and R 4 are hydrogen
  • R 5 is hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci-C4- alkyl)amino
  • R 3 and R 5 are hydrogen
  • R 4 is hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci-C4- alkyl)amino
  • triazines of the formula I corresponds to formula I wherein R 3 , R 4 and R 5 are hydrogen
  • variables R 1 and R 2 have the meanings, in particular the preferred meanings, as defined above; most preference is given to the compounds of the formulae l.a.1 to l.a.294 of Table 1 , where the definitions of the variables R 1 and R 2 are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own:
  • triazines of formula l.b particularly preferred the triazines of formulae l.b.1 to l.b.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3 is F:
  • triazines of formula l.c particularly preferred the triazines of formulae l.c.1 to l.c.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3
  • triazines of formula l.d particularly preferred the triazines of formulae l.d.1 to l.d.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3
  • triazines of formula l.e particularly preferred the triazines of formulae l.e.1 to l.e.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3
  • triazines of formula l.f particularly preferred the triazines of formulae l.f.1 to l.f.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3
  • triazines of formula l.g particularly preferred the triazines of formulae l.g.1 to l.g.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3
  • triazines of formula I.h particularly preferred the triazines of formulae I.h.1 to l.h.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3
  • triazines of formula l.i particularly preferred the triazines of formulae l.i.1 to l.i.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3
  • triazines of formula l.k particularly preferred the triazines of formulae l.k.1 to l.k.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3
  • triazines of formula I.I particularly preferred the triazines of formulae 1.1.1 to 1.1.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 3 is N(CH 3 ) 2 :
  • triazines of formula l.m particularly preferred the triazines of formulae l.m.1 to l.m.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in th 4 is F:
  • triazines of formula l.n particularly preferred the triazines of formulae l.n.1 to l.n.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R 4
  • triazines of formula l.o particularly preferred the triazines of formulae 1.0.1 to I.O.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R 4
  • triazines of formula l.p particularly preferred the triazines of formulae l.p.1 to l.p.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R 4
  • triazines of formula l.q particularly preferred the triazines of formulae l.q.1 to l.q.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 4
  • triazines of formula l.r particularly preferred the triazines of formulae l.r.1 to l.r.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 4
  • triazines of formula l.s particularly preferred the triazines of formulae l.s.1 to l.s.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 4
  • triazines of formula l.t particularly preferred the triazines of formulae l.t.1 to l.t.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 4
  • triazines of formula l.u particularly preferred the triazines of formulae l.u.1 to l.u.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R 4 is S0 2 CH 3 :
  • triazines of formula l.v particularly preferred the triazines of formulae l.v.1 to l.v.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R 4 is N(CH 3 ) 2 :
  • triazines of formula l.v particularly preferred the triazines of formulae l.w.1 to l.w.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R 3 and R 4 are CH 3 :
  • triazines of formula l.v particularly preferred the triazines of formulae l.x.1 to l.x.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R 3
  • triazines of formula l.v particularly preferred the triazines of formulae l.y.1 to l.y.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R 4 is Br:
  • the triazines of formula I according to the invention can be prepared by standard processes of organic chemistry, for example by the following processes: Process A)
  • Y stands for R 2 which is hydroxy
  • L 1 stand for a nucleophilically displaceable leaving group such as hydroxy, C1-C6- alkoxy or benzyloxy, wherein the benzyl ring might be substituted by one to five nitro groups; preferably is hydroxy, Ci-C6-alkoxy or 4-N02-benzyloxy, particularly preferred is hydroxyl or Ci-C6-alkoxy, especially preferred is hydroxy or methoxy.
  • keto-compounds of formula II with amidrazones of formula III is usually carried out at temperature from 0 °C to the boiling point of the reaction mixture, preferably at temperature from 0 °C to 300 °C, particularly preferably at temperature from 10 °C to 200 °C, in an inert organic solvent (e.g. Journal of Organic Chemistry 1987, 52(19), 4287-92).
  • Suitable solvents are aromatic hydrocarbons such as tolene, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert. -butyl methyl- ether, dioxane, anisole and tetrahydrofuran, alkoholes such as methanol, ethanol, n- propanol, isopropanol, n-butanol and tert.-butanol. Particular preference is given to toluene, ethanol and iso-butanol.
  • keto compounds of formula II are generally reacted with one another in equimolar amounts. It may be advantageous to use either an excess of the keto compounds of formula II or of the amidrazones of formula III. Preferably the keto compounds of formula II and the amidrazones of formula III are used in equimolar amounts.
  • reaction mixtures are worked up in a customary manner, for example by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product.
  • Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately elevated temperature.
  • purification can also be carried out by recrystallisation or digestion.
  • Ci-C6-alkylthiocarbonyloxy or di(Ci-C6-alkyl)aminocarbonyloxy R A in formula IV stands for Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl or di(Ci-C6- alkyl)aminocarbonyl.
  • L 2 in formula IV stands for a nucleophilically displaceable leaving group such as halogen, Ci-C6-alkoxy, Ci-C6-alkylcarbonyloxy, Ci-C6-alkoxycarbonyloxy, C1-C6- haloalkylcarbonyloxy, Ci-C6-haloalkoxycarbonyloxy Ci-C6-alkylsulfonyloxy, C1-C6- haloalkylsulfonyloxy, arylsulfonyloxy.
  • L 2 is halogen, particularly preferred CI.
  • Especially preferred electrophiles of formula IV are 0-(Ci-C6-alkyl)-chloridocarbonates, S-(Ci-C6-alkyl)-chloridothiocarbonates and N,N-di(Ci-C6-alkyl)carbamoyl chlorides.
  • reaction of triazines of formula I, wherein R 2 is hydroxyl, with electrophiles of formula IV is usually carried out at from -78 °C to the boiling point of the reaction mixture, preferably at from -78°C to100°C, particularly preferably at from -20°C to 40°C, in an inert organic solvent in the presence of a base (e.g. Tetrahedron 2010, 66, 7544-
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons such as tolene, o-, m- and p- xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert- butyl methylether, dioxane, anisole and tetrahydrofuran, as well as dimethylformamide and ⁇ , ⁇ -dimethylacetamide or N.methylpyrrolidone. Particular preference is given to dichloromethane and tetrahydrofuran.
  • Suitable bases are, inorganic compounds such as 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, and furthermore organic bases, such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and 4-dimethylaminopyridine and also bicyclic amines. Particular preference is given to triethylamine,
  • diisopropylethylamine pyridine and 4-dimethylaminopyridine.
  • the bases are generally employed in equimolar amounts, however they can also be employed in catalytic amounts, in excess or, if appropriate, be used as solvent.
  • triazines of formula I wherein R 2 is hydroxy in train can also be reacted with isocyanates of formula V to give triazines of formula I wherein R 2 is aminocarbonyloxy or (Ci-C6-alkyl)aminocarbonyloxy:
  • Particularly preferred isocyanates of formula V are sulfuryl chloride isocyanate and N- (Ci -C6-a I kyl) i socya nates .
  • the reaction of triazines of formula I with the isocyanates of formula V is usually carried out at from -78 °C to the boiling point of the reaction mixture, preferably at from 0°C to100°C, particularly preferably at from room temperature °C to 100°C, in an inert organic solvent (e.g. J. Med. Chem. 201 1 , 54, 4324-4338; WO 07/123892).
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons such as tolene, o-, m- and p- xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert- butyl methylether, dioxane, anisole and tetrahydrofuran, as well as dimethylformamide and ⁇ , ⁇ -dimethylacetamide or N.methylpyrrolidone. Particular preference is given to dichloromethane and tetrahydrofuran.
  • triazines of formula I wherein R 2 is hydroxy in train can also be reacted with a halogenating agent to give triazines of formula I wherein R 2 is halogen:
  • the reaction of the triazines of formula I wherein R 2 is hydroxy with the halogenating agent IV is usually carried out at from -78°C to the boiling point of the reaction mixture, preferably at from 0°C to 200°C, particularly preferably at from 0°C to 80°C optionally in an inert organic solvent, optionally in the presence of a base (e.g. Liebigs Ann. Chem. 1990, 631 -40).
  • Suitable halogenating agents are e.g. POCI 3 , POBr 3 , PCI 3 , PBr 3 , PCI 5 , PBr 5 , SOC , SOBr2, oxalyl chloride, phosgene, diphosgene and triphosgen.
  • Preferred halogenating agents are POCI 3 , POBr 3 , SOC and oxalyl chloride.
  • Particularly preferred is POCI 3 .
  • the reaction is carried out in the presence of a base. Suitable bases are arylamines such as dimethylaniline.
  • the reactants can be reacted with one another as such, that is to say without any additional solvent. However, it is advantageous to add an inert solvent or mixtures thereof.
  • Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert. -butyl methylether, dioxane, anisole and tetrahydrofuran. Particular preference is given to dichloromethane, chloroform and tetrahydrofuran. It is also possible to use mixtures of the solvents mentioned.
  • R 2 is CN, SH, Ci-Ce-alkoxy, Ci-C 6 -alkylthio, Ci-C 6 -alkoxy-Ci-C 4 -alkoxy, Ci-C 6 -alkoxy- Ci-C 4 -alkylthio, Ci-C 6 -alkylthio-Ci-C 4 -alkoxy, Ci-C 6 -alkyltio-Ci-C 4 -alkylthio, Ci-C 6 - alkoxycarbonyl-Ci-C6-alkoxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
  • heteroaryl which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C1-C6- haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, C1-C6- alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci-
  • Ci-C6-alkylthio-Ci-C 4 -alkyl hydroxycarbonyl, thiocarboxy, C1-C6- alkoxycarbonyl-Ci-C 4 -alkyl, Ci-C6-alkylthiocarbonyl-Ci-C 4 -alkyl, NH2, (Ci- C6-alkyl)amino or di(Ci-C6-alkyl)amino,
  • phenyls are unsubstituted or substituted by one to five substit-uents selected from the group consisting of halogen, CN, NO2, Ci-C 4 -alkyl, C1-C4- alkoxy, Ci-C 4 -haloalkyl, Ci-C 4 -haloalkoxy: koxy- 0-C4-alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio,
  • Ci-C6-alkylthio-CrC4-alkoxy Ci-C6-alkylthio- Ci -C4-al ky I th i o , C 1 -C6-al koxycarbonyl-Ci -C6-al ky oxy , a five membered heteroaryl having 1 to 4 N-atoms, phenoxy or phenyl-Ci-C4-alkoxy
  • R c in formula VI stands for CN, SH, Ci-C 6 -alkoxy, d-Ce-alkylthio, Ci-C 6 -alkoxy-Ci-C 4 - alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkyltio-Ci-C4- alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms, which heteroaryl is attached to the triazine ring via a nitrogen atom
  • heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C1-C6- haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, C1-C6- alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci-
  • Ci-C6-alkylthio-Ci-C4-alkyl hydroxycarbonyl, thiocarboxy, C1-C6- alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci- C6-alkyl)amino or di(Ci-C6-alkyl)amino,
  • phenyls are unsubstituted or substituted by one to five substit-uents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • the reaction of triazines of formula I wherein R 2 is halogen with nucleophiles of formula VI is usually carried out at from -78 °C to the boiling point of the reaction mixture, preferably at from -78°C to100°C, particularly preferably at from 0°C to 80°C, in an inert organic solvent in the presence of a base (e.g. J. Org. Chem. 1987, 52 (19), 4287- 4292).
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use an excess of the nuceophile of formula VI.
  • Suitable solvents are aromatic hydrocarbons such as tolene, 0-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert. -butyl methylether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, as well as dimethylsulfoxide, dimethylformamide and N,N-dimethylacet- amide or N-methylpyrrolidone. Particular preference is given to tetrahydrofuran and dimethylformamide.
  • Suitable bases are, in general inorganic compounds such as alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, and furthermore organic bases, such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and 4- dimethylaminopyridine and also bicyclic amines. Particular preference is given to sodium hydride, triethylamine and 4-dimethylaminopyridine.
  • the bases are generally employed in equimolar amounts, however they can also be employed in catalytic amounts, in excess or, if appropriate, be used as solvent.
  • keto compounds of formula II required for the preparation of the triazines of formula I wherein R 2 is hydroxy are known from the literature (e.g. Org. Lett. 2010, 12, 2864-2867, Org. Lett. 2010, 12, 4424-4427). They can be prepared in accordance with the literature cited and/or are commercially available.
  • amidrazones of formula III required for the preparation of the triazines of formula I wherein R 2 is hydroxy are known from the literature (e.g. Russian Chemical Bulletin 2010, 59, 1808-1816; Org. Lett. 2007, 9, 171 1 -1714). They can be prepared in accordance with the literature cited and/or are commercially available.
  • the electrophiles of formula IV required for the preparation of the triazines of formula I wherein R 2 is Ci-C6-alkoxycarbonyloxy, Ci-C6-alkylthiocarbonyloxy or di(Ci-C6- alkyl)aminocarbonyloxy are commercially available.
  • the isocyanates of formula V required for the preparation of triazines of formula I wherein R 2 is aminocarbonyloxy or (Ci-C6-alkyl)aminocarbonyloxy are commercially available.
  • nucleophils of formula VI required for the preparation of triazines of formula I wherein R 2 is CN, SH, Ci-C 6 -alkoxy, d-Ce-alkylthio, Ci-C 6 -alkoxy-Ci-C 4 -alkoxy, Ci-C 6 - alkoxy-Ci-C 4 -alkylthio, Ci-C6-alkylthio-Ci-C 4 -alkoxy, Ci-C6-alkyltio-Ci-C 4 -alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms, which heteroaryl is attached to the triazine ring via a nitrogen atom and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-
  • phenyls are unsubstituted or substituted by one to five substit-uents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- haloalkyl and Ci-C4-haloalkoxy
  • the triazines I and compositions comprising them are suitable as herbicides. They are suitable as such or as an appropriately formulated composition.
  • the herbicidal compositions comprising the triazines of formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
  • the triazines I or compositions comprising them can additionally be employed in a further number of crop plants for eliminating undesirable plants.
  • suitable crops are the following:
  • Preferred crops are the following: Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max,
  • Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
  • the triazines of formula I according to the invention can also be used in genetically modified plants.
  • genetically modified plants is to be understood as plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species' genome or to exhibit a deletion of DNA that was native to that species' genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone.
  • a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technique.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or
  • polypeptides e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.
  • auxin herbicides such as dicamba or 2,4-D
  • bleacher herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors
  • acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones
  • enolpyruvyl shikimate 3- phosphate synthase (EPSP) inhibitors such as glyphosate
  • glutamine synthetase (GS) inhibitors such as glufosinate
  • protoporphyrinogen-IX oxidase inhibitors lipid-N
  • biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering; furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.
  • ACCase acetyl CoA carboxylase
  • oxynil i. e. bromoxynil or ioxynil
  • Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are under development or commercially available under the brands or trade names RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).
  • herbicides such as glyphosate, imidazolinones and glufosinate, some of which are under development or commercially available under the brands or trade names RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g., VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g., Photorhabdus spp.
  • delta-endotoxins e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c
  • VIP vegetative insecticid
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins;
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize- RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3- hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases.
  • RIP ribosome-inactivating proteins
  • these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g., WO 02/015701 ).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g., in the publications mentioned above.
  • These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles
  • NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e. g., Agrisure® CB) and Bt176 from
  • Syngenta Seeds SAS, France (corn cultivars producing the CrylAb toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from
  • potato culti-vars which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum) or T4-lyso-zym (e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora).
  • T4-lyso-zym e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • productivity e.g., bio-mass production, grain yield, starch content, oil content or protein content
  • tolerance to drought e.g., salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • the triazines of the formula I according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for desiccating and/or defoliating plants using the triazines of the formula I have been found.
  • the triazines of the formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
  • Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pernicious fruit, stone fruit and nuts.
  • the same mechanism i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one triazine of formula I according to the invention.
  • the agrochemical composition comprises a pesticidally effective amount of a c triazine of formula I.
  • effective amount denotes an amount of the composition or of the compounds I, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic conditions and the specific triazine of formula I used.
  • the triazine of formula I can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • agrochemical composition types 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, pastilles, wettable powders or dusts (e.g.
  • WP WP
  • SP WS
  • DP DS
  • pressings e.g. BR, TB, DT
  • granules e.g. WG, SG, GR, FG, GG, MG
  • insecticidal articles e.g. LN
  • gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
  • agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti- foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalene, alkylated
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.g. cellulose, starch
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof.
  • Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes,
  • sulfosuccinates or sulfosuccinamates examples include sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters.
  • carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants e.g. in red, blue, or green
  • Suitable colorants are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • a triazine of formula I according to the invention 5-25 wt% of a triazine of formula I according to the invention and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
  • dispersant e. g. polyvinylpyrrolidone
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a triazine of formula I In an agitated ball mill, 20-60 wt% of a triazine of formula I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 0,1 -2 wt% thickener e.g. xanthan gum
  • a triazine of formula I 50-80 wt% of a triazine of formula I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • a triazine of formula I 50-80 wt% of a triazine of formula I according to the invention are ground in a rotor- stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -3 wt% wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a compound I according to the invention In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1 -5 wt% thickener e.g. carboxymethylcellulose
  • 5-20 wt% of a triazine of formula I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alkohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a triazine of formula I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a protective colloid e.g. polyvinyl alcohol
  • Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a triazine of formula I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
  • diphenylmethene-4,4'-diisocyanatae are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a protective colloid e.g. polyvinyl alcohol.
  • a polyamine e.g.
  • hexamethylenediamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1 -10 wt%.
  • the wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • 1 -10 wt% of a triazine of formula I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • Granules 0.5-30 wt% of a triazine of formula I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • solid carrier e.g. silicate
  • a triazine of formula I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • organic solvent e.g. aromatic hydrocarbon.
  • the agrochemical compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
  • auxiliaries such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Water-soluble concentrates (LS), Suspoemulsions (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 usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
  • compositions thereof, respectively, on to plant propagation material especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
  • triazine of formula I or the agrochemical compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.
  • the rates of application of the triazines of formula I according to the present invention are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.
  • the application rates of the triazine of formula I are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha of active substance (a.s.).
  • the application rate of the triazine of formula I is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha, of active substance.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required.
  • the triazines I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • components comprising triazine of formula I and/or optionally other presticides, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • components comprising triazine of formula I and/or optionally other presticides can be applied jointly (e.g. after tank mix) or consecutively.
  • the triazines of the formula I or the compositions comprising them can be applied pre-, post-emergence or pre-plant, or together with the seed of a crop plant. It is also possible to apply the herbicidal composition or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesirable plants growing underneath, or the bare soil surface (post- directed, lay-by).
  • the triazines of the formula I or the compositions comprising them can be applied by treating seed.
  • the treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the triazine of the formula I according to the invention or the compositions prepared therefrom.
  • the herbicidal compositions can be applied diluted or undiluted.
  • seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
  • seed describes corns and seeds.
  • the seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
  • the triazines of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active ingredient groups and then applied concomitantly.
  • Suitable components for mixtures are, for example herbicides from the classes of the
  • triazines of the formula I alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or
  • phytopathogenic fungi or bacteria Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies.
  • mineral salt solutions which are employed for treating nutritional and trace element deficiencies.
  • Other additives such as non-phytotoxic oils and oil concentrates may also be added.
  • Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the triazines of the formula I towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post- emergence application of the useful plant. The safeners and the triazines of the formula I can be applied simultaneously or in succession.
  • Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H-1 ,2,4- triazol-3-carboxylic acids, 1 -phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha- oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4- (aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4- (haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenyl-
  • Step 1 To a solution of pyrimidine-2-carbonitrile (5.00 g, 47.6 mmol) in ethanol (50 ml) was added hydrazine hydrate (2.31 ml, 47.6 mmol). The resulting solution was stirred at 75°C for four hours. The mixture was subsequently concentrated in vacuum to give crude N' -aminopyrimidine-2-carboxamide (6.46 g, 99 %) as a yellow syrup, which was used directly in step 2 without further purification.
  • Step 2 To a solution of N' -aminopyrimidine-2-carboxamidine in ethanol (50 ml) was added 4-methyl-2-oxo-pentanoic acid (7.43 g, 57.1 mmol).
  • Part B Use examples
  • the culture containers used were plastic pots containing loamy sand with
  • the active compounds suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles.
  • the containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants unless this was adversely affected by the active compounds.
  • test plants were grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. To this end, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
  • the plants were kept at 10 - 25°C and 20 - 35°C, respectively.
  • the test period extended over 2 to 4 weeks. During this time, the plants were tended and their response to the individual treatments was evaluated.
  • Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage or normal course of growth. Good herbicidal activity is given at values of at least 70, and very good herbicidal activity is given at values of at least 85.
  • test period extended over 20 and 21 days, respectively. During this time, the plants were tended, and their reaction to the treatment with active compound was monitored.
  • X percent activity using active compound A at an application rate a
  • E expected activity (in %) by A + B at application rates a + b.
  • the plants used in the greenhouse experiments were of the following species:
  • Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
  • the compounds I. a.43, I. a.44, I. a.46 and I. a.45 applied by the post-emergence method showed very good herbicidal activity against Abutilon theophrasti and Setaria faberi.
  • the compounds I. a.422 wherein R 1 is (Chb ⁇ CHs and R 2 is OH, l.a.428 wherein R is CH 2 CH(CH3)CH2CH 2 CH3 and R 2 is OH, l.a.51 , I. a.58 and I. a.132 applied by the post-emergence method showed very good herbicidal activity against Amaranthus retroflexus and Chenopodium album.
  • the compound I. a.434 wherein R 1 is C(CHs)3 and R 2 is OH applied by the post-emergence method showed very good herbicidal activity against Matricaria inodora and at an application rate of 3000 g/ha good herbicidal activity against Abutilon theophrasti and Setaria faberi.
  • the compound l.a.432 wherein R 1 is CH(C2H 5 )2 and R 2 is OH applied by the post-emergence method showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album, Polygonum convolvulus and Setaria viridis.
  • the compound I. a.47 applied by the post-emergence method showed very good herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Polygonum convolvulus and Setaria viridis.
  • the compounds I. a.48 and l.a.441 wherein R 1 is cyclohexyl and R 2 is OH applied by the post-emergence method showed very good herbicidal activity against Abutilon theophrasti.
  • CH2CH(CH3)CH2CH3 and R 2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
  • CH2CH2CH(CH3)2 and R 2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
  • CH2CH2CH2CH(CH3)2 and R 2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
  • the compound l.a.427 wherein R 1 is CH2CH(C2H 5 )2 and R 2 is OH applied by the post-emergence method showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
  • the compound l.a.430 wherein R 1 CH2CH(CH3)CH(CH3)2 is and R 2 is OH applied by the post-emergence method showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album and Polygonum convolvulus.
  • the compounds I. a.71 and l.a.453 wherein R 1 is CH2CH2SCH3 and R 2 is OH applied by the post-emergence method showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album and Galium aperine.
  • the compound l.a.442 wherein R 1 is CH2-cyclobutyl and R 2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
  • the compound l.a.443 wherein R 1 is CH2-cyclopentyl and R 2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
  • the compound l.a.444 wherein R 1 is CH2-cyclohexyl and R 2 is OH applied by the post-emergence method showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album, Polygonum convolvulus and Galium aperine.
  • the compounds l.a.468 and l.a.485 applied by the post-emergence method showed very good herbicidal activity against Echinocloa crus- galli, Polygonum convolvulus and Setaria viridis.
  • the compounds l.a.468 and l.a.485 applied by the post-emergence method showed very good herbicidal activity against Echinocloa crus- galli, Polygonum convolvulus and Setaria viridis.
  • At an application rate of 500 g/ha compound l.a.484, at an application rate of 798 g/ha compound I. a.459 and at an application rate of 1000 g/ha compound I. a.71 applied by the post-emergence method showed very good herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria viridis.
  • the compounds I. a.490 applied by the post- emergence method showed good herbicidal activity against Chenopodium album and Polygonum convolvulus.

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Abstract

The present invention relates to triazines the general formula I, wherein the variables are defined according to the description, including their agriculturally acceptable salts or, provided that the triazines of formula I have a carboxyl group, their agriculturally acceptable derivatives, in particular to processes for the preparation of said triazines. The invention further relates to compositions comprising compound of formula I and processes for the preparation of these compositions. Further it relates to use of the triazines of formula I as an herbicide as well as to a method of controlling undesired vegetation.

Description

Herbicidal triazines
The present invention relates to trianzines of the general formula I defined below, to a process for their preparation and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation.
WO 09/138712 describes structurally similar compounds for which herbicidal action is stated.
However, the herbicidal properties of these known compounds with regard to the harmful plants are not always entirely satisfactory.
It is therefore an object of the present invention to provide triazines having improved herbicidal action. To be provided are in particular triazines which have high herbicidal activity, in particular even at low application rates, and which are sufficiently compatible with crop plants for commercial utilization.
These and further objects are achieved by triazines of the formula I, defined below, and by their agriculturally suitable salts.
Accordingly, the present invention provides triazines of formula I
Figure imgf000002_0001
R1 is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, d-Cs-alkoxy, d-Cs-alkoxy-Ci-Cs- alkyl, Ci-Cs-alkylthio, C-i-Cs-alkylthio-C-i-Cs-alkyl, hydroxy-Ci-Cio-alkyl, aminocarbonyl, (Ci-C6-alkyl)aminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C8-alkyl, C3-C6-cycloalkyl-Ci-C8- haloalkyl, C3-C6-cycloalkyl-C2-C8-alkenyl or C3-C6-cycloalkyl-C2-C8- haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl and C2-C6-haloalkynyl; is halogen, CN, OH, SH , Ci-C6-alkoxy, d-Ce-alkylthio, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4-alkoxy, C1-C6- alkyltio-Ci-C4-alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxy- carbonyloxy, Ci-C6-alkylthiocarbonyloxy, aminocarbonyloxy, (C1-C6- alkyl)aminocarbonyloxy, di(Ci-C6-alkyl)aminocarbonyloxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, Ci- C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino and di(Ci- C6-alkyl)amino,
phenoxy or phenyl-Ci-C4-alkoxy,
which phenyls are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy; independently of one another are hydrogen, halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkyl)- amino or di(Ci-C6-alkyl)amino; including their agriculturally acceptable salts or, provided that the triazines of formula I have a carboxyl group, their agriculturally acceptable derivatives.
Preferred are the triazines of the formula (I), wherein is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2- C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio, Ci-C6-alkylthio-Ci-C4-alkyl, aminocarbonyl, (C1-C6- alkyl)aminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl or C3-C6-cycloalkyl-C2-C6-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl and C2-C6-haloalkynyl; R2 is halogen, CN, OH, SH, Ci-C6-alkoxy, d-Ce-alkylthio, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4-alkoxy, C1-C6- alkyltio-Ci-C4-alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxy- carbonyloxy, Ci-C6-alkylthiocarbonyloxy, aminocarbonyloxy, (C1-C6- alkyl)aminocarbonyloxy, di(Ci-C6-alkyl)aminocarbonyloxy or a 5- membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, Ci- C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino and di(Ci-
C6-alkyl)amino;
R3, R4 and R5 independently of one another are hydrogen, halogen, CN, NO2,
Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkyl)- amino or di(Ci-C6-alkyl)amino; including their agriculturally acceptable salts or, provided that the triazines of formula I have a carboxyl group, their agriculturally acceptable derivatives.
The present invention also provides the use of triazines of the general formula I as herbicides, i.e. for controlling harmful plants or for desiccation/defoliation of plants.
The present invention also provides compositions comprising at least one triazine of the formula I and auxiliaries customary for formulating crop protection agents.
In particular, the subject of the present invention are agrochemical compositions comprising a herbicidal active amount of at least one triazine of formula I and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substance.
A process for the preparation of herbicidal active agrochemical compositions, which comprises mixing a herbicidal active amount of at least one triazine of formula I and at least one inert liquid and/or solid carrier and, if desired, at least one surface- active substance is also the subject of the present invention.
The present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one triazine of the formula I is allowed to act on plants, their seeds and/or their habitat. Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants. Moreover, the invention relates to processes for preparing the triazines of the formula I.
Further embodiments of the present invention are evident from the claims, the description and the examples. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention. As used herein, the terms "controlling" and "combating" are synonyms.
As used herein, the terms "undesirable vegetation" and "harmful plants" are synonyms.
If the triazines of formula I as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
If the triazines of formula I as described herein have one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions according to the invention.
If the triazines of formula I as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4- alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2- (2-hydroxyeth-1 -oxy)eth-1 -ylammonium (diglycolamine salt), di(2-hydroxyeth-1 -yl)- ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2- hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, Ν,Ν,Ν- trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Triazines of formula I as described herein having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-C6-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl
((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as C1-C10- alkylthio esters. Preferred mono- and di-Ci-C6-alkylamides are the methyl and the dimethylamides. Preferred arylamides are, for example, the anilides and the 2- chloroanilides. Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), meptyl (1 -methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester. An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
The organic moieties mentioned in the definition of the variables R1 to R5 are - like the term halogen - collective terms for individual enumerations of the individual group members. The term halogen denotes in each case fluorine, chlorine, bromine or iodine. All hydrocarbon chains, i.e. all alkyl, alkenyl, alkynyl, alkoxy and alkylthio chains can be straight-chain or branched, the prefix Cn-Cm denoting in each case the possible number of carbon atoms in the group. The meaning of certain generic terms used herein is explained below:
Ci-C2-alkyl and also the Ci-C2-alkyl moieties of composite groups: CH3 and C2H5; Ci-C3-alkyl and also the Ci-C3-alkyl moieties of composite groups: Ci-C2-alkyl as mentioned above, and also n-propyl and i-propyl;
Ci-C4-alkyl and also the Ci-C4-alkyl moieties of Ci-C6-alkyoxy-Ci-C4-alkyl, C1-C6- alkylthio-Ci-C4-alkyl, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C4- alkyl: for example CH3, C2H5, n-propyl and CH(CH3)2, n-butyl, CH(CH3)C2H5,
CH2CH(CH3)2 and C(CH3)3;
Ci-C6-alkyl and also the Ci-C6-alkyl moieties of Ci-C6-alkyoxy-Ci-C6-alkyl and C3- C6-cycloalkyl-Ci-C6-alkyl: Ci-C4-alkyl as mentioned 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;
- Ci-Cs-alkyl and also the Ci-Cs-alkyl moieties of composite groups such as alkoxy or alkylthio: Ci-C6-alkyl as mentioned above, and also, for example, n-heptyl, n-octyl or positional isomers thereof, e.g. 2-ethylhexyl or 2,3-dimethylpentyl;
Ci-Cio-alkyl and also the Ci-Cio-alkyl moieties of composite groups such as hydroxyalkyl: Ci-Cs-alkyl as mentioned above, and also, for example, n-nonyl, n-decyl or positional isomers thereof;
Ci-C4-haloalkyl: Ci-C4-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-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, heptafluoropropyla Ci-C3-haloalkyl radical as mentioned above, and also, for example, 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;
Ci-C6-haloalkyl and also the Ci-C6-haloalkyl moieties of C3-C6-cycloalkyl-Ci-C6- haloalkyi: Ci-C4-haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6- chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;
Ci-Cs-haloalkyI: Ci-C6-haloalkyl as mentioned above, and also, for example, n- heptyl, n-octyl or positional isomers thereof where one or more hydrogen atoms in these groups are replaced by halogen atoms as aforesaid;
C3-C6-cycloalkyl and also the C3-C6-cycloalkyl moieties of C3-C6-cycloalkyl-Ci-C6- alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl and C3-C6- cycloalkyl-C2-C6-haloalkenyl: a monocyclic saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
- C3-C6-alkenyl: for example 1 -propenyl, 2-propenyl, 1 -methylethenyl, 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;
C2-C6-alkenyl and also the C2-C6-alkenyl moieties of C3-C6-cycloalkyl-C2-C6- alkenyl: C3-C6-alkenyl as mentioned above, and also ethenyl;
C2-C8-alkenyl and also the alkenyl moieties in composite groups: C2-C6-alkenyl as mentioned above, and also, for example, n- heptenyl, n-octenyl or positional isomers thereof having one double bond in any position, e.g. 1 -heptenyl, 2-heptenyl, 3-heptenyl, 1 -octenyl, 2-octenyl, 3-octenyl and 4-octenyl;
C2-Cio-alkenyl and also the alkenyl moieties in composite groups: C2-Cs-alkenyl an mentioned above and also, for example, n-decenyl, n-nonenyl or positional isomers thereof having one double bond in any position;
- C2-C6-haloalkenyl and also the C2-C6-haloalkenyl moieties of C3-C6-cycloalkyl-C2- C6-haloalkenyl: C2-C6-alkenyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 2-chloroprop-2-en-1 -yl, 3- chloroprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1 -yl, 3,3-dichloroprop-2-en-1 -yl, 2,3,3- trichloro-2-en-1 -yl, 2,3-dichlorobut-2-en-1 -yl, 2-bromoprop-2-en-1 -yl, 3-bromoprop-2- en-1 -yl, 2,3-dibromoprop-2-en-1 -yl, 3,3-dibromoprop-2-en-1 -yl, 2,3,3-tribromo-2-en-1 -yl or 2,3-dibromobut-2-en-1 -yl;
C2-C8-haloalkenyl and also the alkenyl moieties in composite groups: C2-C6- haloalkenyl as mentioned above, and also, for example, 3-fluoro-n-heptenyl-1 , 1 ,3,3,- trichloro-n-heptenyl-5 and 1 ,3,5-trichloro-n-octenyl-6;
- C3-C6-cycloalkenyl: 1 -cyclopropenyl, 2-cyclopropenyl, 1 -cyclobutenyl, 2-cyclo- butenyl, 1 -cyclopentenyl, 2-cyclopentenyl, 1 ,3-cyclopentadienyl, 1 ,4-cyclopentadienyl, 2,4-cyclopentadienyl, 1 -cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1 ,3-cyclohexa- dienyl, 1 ,4-cyclohexadienyl, 2,5-cyclohexadienyl;
C3-C6-alkynyl: for example 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1 -methyl-2-butynyl, 1 -methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1 ,1 -dimethyl-2-propynyl, 1 - ethyl-2-propynyl, 1 -hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2- pentynyl, 1 -methyl-3-pentynyl, 1 -methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4- pentynyl, 3-methyl-1 -pentynyl, 3-methyl-4-pentynyl, 4-methyl-1 -pentynyl, 4-methyl-2- pentynyl, 1 ,1 -dimethyl-2-butynyl, 1 ,1 -dimethyl-3-butynyl, 1 ,2-dimethyl-3-butynyl, 2,2- dimethyl-3-butynyl, 3,3-dimethyl-1 -butynyl, 1 -ethyl-2-butynyl, 1 -ethyl-3-butynyl, 2-ethyl- 3-butynyl and 1 -ethyl-1 -methyl-2-propynyl; C2-C6-alkynyl: C3-C6-alkynyl as mentioned above and also ethynyl;
C2-C8-alkynyl: C2-C6-alkynyl as mentioned above, and also, for example, n- heptinyl, n-octinyl or positional isomers thereof having one or two triple bonds in any position, e.g. 1 -heptynyl, 2-heptynyl, 1 -octynyl and 2-octynyl;
- C2-Cio-alkynyl: C2-Cs-alkynyl mentioned above and also, for example, n-decynyl, n-nonynyl or positional isomers thereof having one or two triple bonds in any position;
C2-C6-haloalkynyl: a C2-C6-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example
1 .1 - difluoroprop-2-yn-1 -yl, 3-chloroprop-2-yn-1 -yl, 3-bromoprop-2-yn-1 -yl, 3-iodoprop- 2-yn-1 -yl, 4-fluorobut-2-yn-1 -yl, 4-chlorobut-2-yn-1-yl, 1 ,1 -difluorobut-2-yn-1 -yl, 4- iodobut-3-yn-1 -yl, 5-fluoropent-3-yn-1 -yl, 5-iodopent-4-yn-1 -yl, 6-fluorohex-4-yn-1 -yl or 6-iodohex-5-yn-1 -yl;
C2-C8-haloalkynyl: C2-C6-haloalkynyl as mentioned above, and also, for example, n-heptynyl, n-octynyl or positional isomers thereof where one or more hydrogen atoms in these groups are replaced by halogen atoms as aforesaid, e.g. 1 -chloro-2-heptynyl and 1 -chloro-2-octynyl;
Ci-C2-alkoxy and also the Ci-C2-alkoxy moieties of composite croups: methoxy and ethoxy;
Ci-C4-alkoxy and also the Ci-C4-alkoxy moieties of Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-C6-alkylthio-Ci-C4-alkoxy: for example methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy, 1 -methylpropoxy, 2-methylpropoxy and 1 ,1 -dimethylethoxy;
Ci-C6-alkoxy and also the Ci-C6-alkoxy moieties of Ci-C6-alkoxy-Ci-C6-alkyl, Ci- C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio, C1-C6- alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, Ci-C6-alkoxycarbonyl, C1-C6- alkoxycarbonyl-Ci-C4-alkyl: Ci-C4-alkoxy as mentioned above, and also, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2- dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2- methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2- dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3- dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1 -ethyl-1 -methylpropoxy and 1 -ethyl-2-methylpropoxy;
Ci-Cs-alkoxy and also the Ci-Cs-alkoxy moieties of composite groups: C1-C6- alkoxy as mentioned above, and also, for example, n-heptoxy, n-octoxy or positional isomers thereof, e.g. 1 ,1 ,3,3-tetramethylbutoxy and 2-ethylhexoxy;
- Ci-C4-haloalkoxy: a Ci-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,
bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy,
2.2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2- fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3- bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3- trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy,
heptafluoropropoxy, 1 -(fluoromethyl)-2-fluoroethoxy, 1 -(chloromethyl)-2-chloroethoxy, 1 -(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;
- Ci-C6-haloalkoxy: a Ci-C4-haloalkoxy as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy,
undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
Ci-C4-alkylthio and also the Ci-C4-alkylthio moieties of Ci-C6-alkoxy-Ci-C4-alkyl- thio, Ci-C6-alkyltio-Ci-C4-alkylthio: for example methylthio, ethylthio, propylthio, 1 - methylethylthio, butylthio, 1 -methylpropylthio, 2-methylpropylthio and 1 ,1 - dimethylethylthio;
Ci-C6-alkylthio and also the Ci-C6-alkylthio moieties of Ci-C6-alkylthio-Ci-C4- alkoxy, Ci-C6-alkyltio-Ci-C4-alkylthio, Ci-C6-alkylthiocarbonyloxy, Ci-C6-alkylthio- carbonyl, Ci-C6-alkylthio-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C4-alkyl: Ci-C4-alkylt- hio as mentioned above, and also, for example, pentylthio, 1 -methylbutylthio, 2-methyl- butylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 ,1 -di- methylpropylthio, 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;
(Ci-C4-alkyl)amino and also the (Ci-C4-alkyl)amino moieties of (Ci-C4-alkyl)ami- nocarbonyl: for example methylamino, ethylamino, propylamino, 1 -methylethylamino, butylamino, 1 -methylpropylamino, 2-methylpropylamino or 1 ,1 -dimethylethylamino;
(Ci-C6-alkyl)amino and also the (Ci-C6-alkyl)amino moieties of (Ci-C6-alkyl)- aminocarbonyl, (Ci-C6-alkyl)aminocarbonyloxy: (Ci-C4-alkylamino) as mentioned 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 -dimethylbutyl- amino, 1 ,2-dimethylbutylamino, 1 ,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3- dimethylbutyl-amino 3,3-dimethylbutylamino, 1 -ethylbutylamino, 2-ethylbutylamino, 1 ,1 ,2-trimethylpropylamino, 1 ,2,2-trimethyl-propylamino, 1 -ethyl-1 -methylpropylamino or 1 -ethyl-2-methylpropylamino;
di(Ci-C4-alkyl)amino and also the di(Ci-C4-alkyl)amino moieties of di(Ci-C4- alkyl)aminocarbonyl: for example N,N-dimethylamino, Ν,Ν-diethylamino, N,N-di(1 - methylethyl)amino, N,N-dipropylamino, Ν,Ν-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 -methyl- ethyl)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-propyl- amino, 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 -methyl- propyl)-N-(2-methylpropyl)amino, N-(1 ,1 -dimethylethyl)-N-(1 -methylpropyl)amino or N- (1 ,1 -dimethylethyl)-N-(2-methylpropyl)amino;
- di(Ci-C6-alkyl)amino and also the di(Ci-C6-alkyl)amino moieties of di(Ci-C6- alkyl)aminocarbonyl, di(Ci-C6-alkyl)aminocarbonyloxy: di(Ci-C4-alkyl)amino as mentioned above, and also, for example, N-methyl-N-pentylamino, N-methyl-N-(1 - methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-methyl-N-(3-methyl- butyl)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-dimethyl- butyl)amino, N-methyl-N-(2,3-dimethylbutyl)amino, N-methyl-N-(3,3-dimethyl- butyl)amino, N-methyl-N- (l -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-di- pentylamino, N-propyl-N-hexylamino, N-butyl-N-hexylamino, N-pentyl-N-hexylamino or N,N-dihexylamino;
Ci-C6-alkylsulfonyl (Ci-C6-alkyl-S(0)2-) : for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1 -methylethylsulfonyl, butylsulfonyl, 1 -methylpropylsulfonyl, 2-methyl- propylsulfonyl, 1 ,1 -dimethylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2- methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-di- methylpropylsulfonyl, 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-trimethyl- propylsulfonyl, 1 ,2,2-trimethylpropylsulfonyl, 1 -ethyl-1 -methylpropylsulfonyl and 1 -ethyl- 2-methylpropylsulfonyl;
a 5-membered heteroaryl having 1 to 4 nitrogen atoms : a monocyclic, aromatic cycle having five ring members and which comprises apart from carbon atoms 1 to 4 nitrogen atoms, for example 1 -pyrrolyl, 1 -pyrazolyl, 1 -imidazolyl, 1 ,2,3— triazol— 1— yl, 1 ,2,4-triazol-1-yl, 1 -tetrazolyl.
The preferred embodiments of the invention mentioned herein below have to be understood as being preferred either independently from each other or in combination with one another. According to a preferred embodiment of the invention preference is also given to those triazines of formula I, wherein the variables, either independently of one another or in combination with one another, have the following meanings: preferably is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-C8-alkynyl, Ci-Cs- haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, C-i-Cs-alkoxy-C-i-Cs-alkyl, Ci-C alkylthio-Ci-C6-alkyl, hydroxy-C-i-Cs-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3 C6-cycloa I kyl-C2-C6-hal oa I kenyl ,
which cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C6-haloalkyl; particulary preferred is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cs-alkynyl, Ci- Cs-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, C-i-Cs-alkoxy-C-i-Cs-alkyl, Ci- C6-alkylthio-Ci-C6-alkyl, hydroxy-C-i-Cs-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3-C6-cycloa I kyl-C2-C6-hal oa I kenyl ,
which cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C3-haloalkyl; especially preferred is Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, C-i-Cs-alkoxy-C-i-Cs-alkyl, Ci-C6-alkylthio- Ci-C6-alkyl, hydroxy-C-i-Cs-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3-C6- cycloalkyl-C2-C6-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to five
substituents, preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C3-haloalkyl; more preferred is Ci-Cio-alkyl, C2-Cio-alkenyl, d-Cs-haloalkyl, C2-C8-haloalkenyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylthio-Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C6-alkyl or C3-C6-cycloalkyl-Ci-C6-haloalkyl,
which cycloalkyls are unsubstituted or substituted by one to five
substituents, preferably by one to three, particularly preferred one or two, more preferred by one substituent(s), selected from the group consisting of halogen and Ci-C6-alkyl; most preferred is Ci-Cio-alkyl, C2-Cio-alkenyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C6-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci-C4- alkyl,
which cycloalkyls are unsubstituted or substituted by one to three substituents, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of Ci-C6-alkyl; preferably is halogen, CN, OH, SH, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxy- Ci-C4-alkoxy, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, Ci-C6-alkylthiocarbonyloxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to four substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci- C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, C1-C6- alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci- C3-alkyl)amino or di(Ci-C3-alkyl)amino,
phenoxy or phenyl-Ci-C4-alkoxy,
which phenyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy; particularly preferred is halogen, CN, OH , SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, C1-C6- alkoxycarbonyloxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to three
substituents, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, C1-C6- alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl or di(Ci-C2-alkyl)amino,
phenoxy or phenyl-Ci-C4-alkoxy,
which phenyls are unsubstituted or substituted by one to five substituents, preferably one to three, particularly preferred one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy or Ci-C4-haloalkyl; especially preferred is halogen, CN, OH, SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, C1-C6- alkoxycarbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to three
substituents, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, C1-C6- alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl or di(Ci-C2-alkyl)amino,
phenoxy or phenyl- Ci-C3-alkoxy,
which phenyls are unsubstituted or substituted by one to five, preferably one to three substituents, particularly preferred one or two substituents selected from the group consisting of halogen, CN , NO2, Ci-C4-alkyl, C1-C4- alkoxy or Ci-C3-haloalkyl; more preferred is halogen, CN, OH, SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, a 5- membered heteroaryl having 2 to 4 nitrogen atoms selected from pyrazoles, imidazoles, 1 ,2,4-triazoles or tetrazoles,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to two substituents selected from the group consisting of halogen, CN , NO2, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C1-C6- alkoxycarbonyl,
phenoxy or phenyl-Ci-C2-alkoxy,
which phenyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of NO2 or Ci-C2-alkoxy; most preferred is halogen, CN, OH , SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy,
Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms selected from pyrazoles, imidazoles,
1 ,2,4-triazoles or tetrazoles
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to two substituents selected from the group consisting of CN, NO2, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkylthio and Ci-C6-alkoxycarbonyl, phenoxy or phenyl-Ci-alkoxy,
which phenyls are unsubstituted or substituted by one to three substituents, particularly preferred one or two substituents selected from the group consisting of NO2 and Ci-alkoxy;
R3, R4 and R5 preferably independently of one another are hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-alkylsulfonyl or di(Ci-C4-alkyl)amino,
preferably at least one of R3, R4 and R5 is H, particularly preferred at least one of R4 and R5 is H, especially preferred R5 is H, more preferred R5 and R3 or R5 and
R4 are H, most preferred R3, R4 and R5 are H; particulary preferred independently of one another are hydrogen, halogen, CN, NO2, Ci-C3-alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkoxy- d-Cs-alkyl or di(Ci-C3-alkyl)amino,
preferably at least one of R3, R4 and R5 is H, particularly preferred at least one of R4 and R5 is H, especially preferred R5 is H, more preferred R5 and R3 or R5 and R4 are H, most preferred R3, R4 and R5 are H; especially preferred independently of one another are hydrogen, halogen, C1-C3- alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy or Ci-C2-alkoxy- C1-C2- alkyl,
preferably at least one of R3, R4 and R5 is H, particularly preferred at least one of R4 and R5 is H, especially preferred R5 is H, more preferred R5 and R3 or R5 and R4 are H, most preferred R3, R4 and R5 are H; more preferred independently of one another are hydrogen, halogen, Ci-C2-alkyl or Ci-C2-alkoxy,
preferably at least one of R3, R4 and R5 is H, particularly preferred at least one of R4 and R5 is H, especially preferred R5 is H, more preferred R5 and R3 or R5 and R4 are H, most preferred R3, R4 and R5 are H; most preferred independently of one another are hydrogen, halogen, Ci-C2-alkyl or Ci-C2-alkoxy,
with a proviso that at least one of R3, R4 and R5 is H, particularly preferred at least one of R4 and R5 is H, especially preferred R5 is H, more preferred R5 and R3 or
R5 and R4 are H, most preferred R3, R4 and R5 are H;
Particular preference is given to triazines of the formula I wherein,
R1 is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cs-alkynyl, C-i-Cs-haloalkyl, C2-C8- haloalkenyl, C2-C8-haloalkynyl, C-i-Cs-alkoxy-C-i-Cs-alkyl, Ci-C6-alkylthio-Ci-C6- alkyl, hydroxy-d-Cs-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6- cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3-C6-cycloalkyl-C2- C6-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C6-haloalkyl; is halogen, CN, OH, SH , Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, C1-C6- alkoxycarbonyloxy, Ci-C6-alkylthiocarbonyloxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to four substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6- alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci- C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, C1-C6- alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci- C3-alkyl)amino or di(Ci-C3-alkyl)amino,
phenoxy or phenyl-Ci-C4-alkoxy,
which phenyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4- alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy; R3, R4 and R5 independently of one another are hydrogen, halogen, CN, NO2, C1-C3- alkyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-haloalkoxy, Ci-C3-alkoxy-Ci-C3-alkyl or di(Ci-C3-alkyl)amino,
with a proviso that at least one of R3, R4 and R5 is H, particularly preferred at least one of R4 and R5 is H, especially preferred R5 is H, more preferred R5 and R3 or
R5 and R4 are H, most preferred R3, R4 and R5 are H;
Additionally, particular preference is given to triazines of the formula I wherein, R1 hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-C0-alkynyl, Ci-Cs-haloalkyl, C2
haloalkenyl, C2-C8-haloalkynyl, Ci-C0-alkoxy-Ci-C0-alkyl, Ci-C6-alkylthio-Ci-C6- alkyl, hydroxy-Ci-C0-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6- cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3-C6-cycloalkyl-C2- C6-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl and Ci-C3-haloalkyl; is halogen, CN, OH, SH, d-Ce-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-Ce- alkylthio-Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxy- carbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to three substituents, particularly preferred by one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, C1-C6- alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl or di(Ci-C2-alkyl)amino,
phenoxy or phenyl- Ci-C3-alkoxy,
which phenyls are unsubstituted or substituted by one to five, preferably one to three substituents, particularly preferred one or two substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy or Ci-Cs-haloalkyl;
R3, R4 and R5 independently of one another are hydrogen, halogen, Ci-C3-alkyl, Ci- C2-haloalkyl, Ci-C2-alkoxy, Ci-C2-haloalkoxy or Ci-C2-alkoxy- Ci-C2-alkyl, with a proviso that at least R5 is H, more preferred R5 and R3 or R5 and R4 are H, most preferred R3, R4 and R5 are H;
Further, particular preference is given to triazines of the formula I wherein, is Ci-Cio-alkyl, C2-Cio-alkenyl, C-i-Cs-haloalkyl, C2-C8-haloalkenyl, Ci-C6-alkoxy- d-Ce-alkyl, Ci-C6-alkylthio-Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6- alkyl or C3-C6-cycloalkyl-Ci-C6-haloalkyl,
which cycloalkyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred one or two, more preferred by one substituent(s), selected from the group consisting of halogen and Ci-C6-alkyll; is halogen, CN, OH, SH , d-Ce-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-Ce- alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms selected from pyrazoles, imidazoles, 1 ,2,4-triazoles or tetrazoles,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to two substituents selected from the group consisting of halogen, CN , NO2, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C1-C6- alkoxycarbonyl,
phenoxy or phenyl-Ci-C2-alkoxy,
which phenyls are unsubstituted or substituted by one to five substituents, preferably by one to three, particularly preferred by one or two substituents selected from the group consisting of NO2 or Ci-C2-alkoxy;
R3, R4 and R5 independently of one another are hydrogen, halogen, Ci-C2-alkyl or Ci-C2-alkoxy,
with a proviso that at least R5 is H, more preferred R5 and R3 or R5 and R4 are H, most preferred R3, R4 and R5 are H;
Additionally, particular preference is given to triazines of the formula I wherein, R1 is Ci-Cio-alkyl, C2-Cio-alkenyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C4- alkylthio-Ci-C4-alkyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci-C4-alkyl,
which cycloalkyls are unsubstituted or substituted by one to three substituents, particularly preferred by one or two, more preferred by one substituent(s), selected from the group consisting of Ci-C6-alkyl; R2 is halogen, CN, OH, SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-C6- alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms selected from pyrazoles, imidazoles, 1 ,2,4-triazoles or tetrazoles
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by one to two substituents selected from the group consisting of CN, NO2, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkylthio and Ci-C6-alkoxycarbonyl, phenoxy or phenyl-Ci-alkoxy,
which phenyls are unsubstituted or substituted by one to three substituents, particularly preferred one or two substituents selected from the group consisting of NO2 and Ci-alkoxy;
R3, R4 and R5 independently of one another are hydrogen, halogen, Ci-C2-alkyl or Ci-C2-alkoxy;
with a proviso that at least R5 is H, more preferred R5 and R3 or R5 and R4 are H, most preferred R3, R4 and R5 are H;
Further, preferred are the triazines of formula I, wherein R1 is
hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C6-alkyl, C3- C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4-cycloalkyl- C2-C6-haloalkenyl
which cycloalkyls are unsubstituted or substituted by one to five, preferably one to three, particularly preferred one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkenyl and C2-C4- haloalkynyl; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4- alkyl, C3-C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4- cycloalkyl-C2-C6-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl and C2-C4-haloalkenyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl; especially preferred C2-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C2-C6-haloalkyl, C3- C6-haloalkenyl, C3-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3-C4- cycloalkyl-C2-C4-haloalkenyl ,
which cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl and C2-C4-haloalkenyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl. Also preferred are the triazines of formula I, wherein R1 is
Ci-C6-alkyl, C2-C6-alkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl or C3-C6-cycloalkyl-C2-C6-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci- C4-alkyl; particularly preferred Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl, C2-C4- haloalkenyl, Cs-Cs-cycloalkyl, C3-C5-cycloalkyl-Ci-C6-alkyl, C3-C5-cycloalkyl-Ci- C6-haloalkyl, C3-C5-cycloalkyl-C2-C6-alkenyl or C3-C5-cycloalkyl-C2-C6-haloalkenyl, which cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-
C4-alkyl; especially preferred Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl, C2-C4- haloalkenyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci- C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3-C4-cycloalkyl-C2-C4-haloalkenyl, which cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; more preferred C2-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkyl, C2-C4-haloalkenyl, C3- C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3- C4-cycloalkyl-C2-C4-alkenyl or C3-C4-cycloalkyl-C2-C4-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl. Also preferred are the triazines of formula I, wherein R1 is
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci- C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3- C6-cycloa I kyl-C2-C6-hal oa I kenyl ,
which cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci- C4-alkyl; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-haloalkyl, C3-C6-cycloalkyl-C2-C4- alkenyl or C3-C6-cycloalkyl-C2-C4-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci- C4-alkyl; especially preferred Ci-C4-alkyl, C2-C4-alkenyl, Cs-Cs-cycloalkyI, Cs-Cs-cycloalkyl- Ci-C2-alkyl, C3-C5-cycloalkyl-Ci-C4-haloalkyl, C3-C5-cycloalkyl-C2-C4-alkenyl or C3-C5-cycloa I kyl-C2-C4-hal oa I kenyl ,
which cycloalkyls are unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; more preferred C2-C4-alkyl, C3-C4-alkenyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci- C2-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3- C4-cycloa I kyl-C2-C4-hal oa I kenyl ,
which cycloalkyls are unsubstituted or substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
Also preferred are the triazines of formula I, wherein R1 is
C2-C6-alkenyl or C3-C6-cycloalkyl, which cycloalkyl isunsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; particularly preferred C2-C4-alkenyl or Cs-Cs-cycloalkyl,
which cycloalkyl is unsubstituted or substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci- C4-alkyl; especially preferred C3-C4-alkenyl or C3-C4-cycloalkyl,
which cycloalkyl is unsubstituted or substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and C1-C2- haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl. more preferred C3-C4-alkenyl or C3-C4-cycloalkyl,
which cycloalkyl is unsubstituted.
Also preferred are the triazines of formula I , wherein R1 is
hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C6-alkyl, C3- C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4-cycloalkyl- C2-C6-haloalkenyl,
which cycloalkyls are unsubstituted; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4- alkyl, C3-C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4- cycloalkyl-C2-C6-haloalkenyl,
which cycloalkyls are unsubstituted; especially preferred C2-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C2-C6-haloalkyl, C3- C6-haloalkenyl, C3-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3-C4- cycloalkyl-C2-C4-haloalkenyl ,
which cycloalkyls are unsubstituted. Also preferred are the triazines of formula I, wherein R1 is
Ci-C6-alkyl, C2-C6-alkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl or C3-C6-cycloalkyl-C2-C6-haloalkenyl,
which cycloalkyls are unsubstituted; particularly preferred Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl, C2-C4- haloalkenyl, Cs-Cs-cycloalkyl, C3-C5-cycloalkyl-Ci-C6-alkyl, Cs-Cs-cycloalkyl-Ci- C6-haloalkyl, C3-C5-cycloalkyl-C2-C6-alkenyl or C3-C5-cycloalkyl-C2-C6-haloalkenyl, which cycloalkyls are unsubstituted; especially preferred Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl, C2-C4- haloalkenyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci- C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3-C4-cycloalkyl-C2-C4-haloalkenyl, which cycloalkyls are unsubstituted; more preferred C2-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkyl, C2-C4-haloalkenyl, C3- C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3- C4-cycloalkyl-C2-C4-alkenyl or C3-C4-cycloalkyl-C2-C4-haloalkenyl,
which cycloalkyls are unsubstituted.
Also preferred are the triazines of formula I, wherein R1 is
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci- C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3-
C6-cycloa I kyl-C2-C6-hal oa I kenyl ,
which cycloalkyls are unsubstituted; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-haloalkyl, C3-C6-cycloalkyl-C2-C4- alkenyl or C3-C6-cycloalkyl-C2-C4-haloalkenyl,
which cycloalkyls are unsubstituted; especially preferred Ci-C4-alkyl, C2-C4-alkenyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyl- Ci-C2-alkyl, C3-C5-cycloalkyl-Ci-C4-haloalkyl, C3-C5-cycloalkyl-C2-C4-alkenyl or
C3-C5-cycloa I kyl-C2-C4-hal oa I kenyl ,
which cycloalkyls are unsubstituted; more preferred C2-C4-alkyl, C3-C4-alkenyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci- C2-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3-
C4-cycloa I kyl-C2-C4-hal oa I kenyl ,
which cycloalkyls are unsubstituted. Also preferred are the triazines of formula I , wherein R1 is
C2-C6-alkenyl or C3-C6-cycloalkyl,
which cycloalkyl is unsubstituted; particularly preferred C2-C4-alkenyl or Cs-Cs-cycloalkyl,
which cycloalkyl is unsubstituted; especially preferred C3-C4-alkenyl or C3-C4-cycloalkyl,
which cycloalkyl is unsubstituted. more preferred C3-C4-alkenyl or C3-C4-cycloalkyl,
which cycloalkyl is unsubstituted.
Also preferred are the triazines of formula I , wherein R1 is
hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C6-alkyl, C3 C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4-cycloalkyl- C2-C6-haloalkenyl
which cycloalkyls are substituted by one to five, preferably one to three, particularly preferred one or two, more preferred by one substituent(s), selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkenyl and C2-C4-haloalkynyl; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4- alkyl, C3-C4-cycloalkyl-Ci-C6-haloalkyl, C3-C4-cycloalkyl-C2-C6-alkenyl or C3-C4- cycloalkyl-C2-C6-haloalkenyl,
which cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl and C2-C4-haloalkenyl, particularly preferred selected from the group consisting of halogen and Ci C4-alkyl; especially preferred C2-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C2-C6-haloalkyl, C C6-haloalkenyl, C3-C6-haloalkynyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3-C4- cycloalkyl-C2-C4-haloalkenyl ,
which cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl and C2-C4-haloalkenyl, particularly preferred selected from the group consisting of halogen and Ci C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
Also preferred are the triazines of formula I, wherein R1 is
Ci-C6-alkyl, C2-C6-alkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl or C3-C6-cycloalkyl-C2-C6-haloalkenyl,
which cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; particularly preferred Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl, C2-C4- haloalkenyl, Cs-Cs-cycloalkyl, C3-C5-cycloalkyl-Ci-C6-alkyl, C3-C5-cycloalkyl-Ci- C6-haloalkyl, C3-C5-cycloalkyl-C2-C6-alkenyl or C3-C5-cycloalkyl-C2-C6-haloalkenyl, which cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; especially preferred Ci-C4-alkyl, C2-C4-alkenyl, Ci-C4-haloalkyl, C2-C4- haloalkenyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci- C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3-C4-cycloalkyl-C2-C4-haloalkenyl, which cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; more preferred C2-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkyl, C2-C4-haloalkenyl, C3- C4-cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3- C4-cycloalkyl-C2-C4-alkenyl or C3-C4-cycloalkyl-C2-C4-haloalkenyl,
which cycloalkyls are substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
Also preferred are the triazines of formula I, wherein R1 is Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or C3-C6-cycloalkyl-Ci- C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-C2-C6-alkenyl or C3- C6-cycloa I kyl-C2-C6-hal oa I kenyl ,
which cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; particularly preferred Ci-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, C3-C6-cycloalkyl-Ci-C4-haloalkyl, C3-C6-cycloalkyl-C2-C4- alkenyl or C3-C6-cycloalkyl-C2-C4-haloalkenyl,
which cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; especially preferred Ci-C4-alkyl, C2-C4-alkenyl, Cs-Cs-cycloalkyI, Cs-Cs-cycloalkyl- Ci-C2-alkyl, C3-C5-cycloalkyl-Ci-C4-haloalkyl, C3-C5-cycloalkyl-C2-C4-alkenyl or C3-C5-cycloa I kyl-C2-C4-hal oa I kenyl ,
which cycloalkyls are substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; more preferred C2-C4-alkyl, C3-C4-alkenyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-Ci- C2-alkyl, C3-C4-cycloalkyl-Ci-C4-haloalkyl, C3-C4-cycloalkyl-C2-C4-alkenyl or C3- C4-cycloa I kyl-C2-C4-hal oa I kenyl ,
which cycloalkyls are substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
Also preferred are the triazines of formula I, wherein R1 is
C2-C6-alkenyl or C3-C6-cycloalkyl,
which cycloalkyl is substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C6-alkyl and Ci-C6-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; particularly preferred C2-C4-alkenyl or Cs-Cs-cycloalkyl,
which cycloalkyl is substituted by one to three, preferably one or two, more preferred by one substituent(s) selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl; especially preferred C3-C4-alkenyl or C3-C4-cycloalkyl,
which cycloalkyl is substituted by one or two substituents selected from the group consisting of halogen, Ci-C2-alkyl and Ci-C2-haloalkyl, particularly preferred selected from the group consisting of halogen and Ci-C4-alkyl, especially preferred selected from the group consisting of fluorine and Ci-C4-alkyl.
Preferred are the triazines of formula I, wherein R2 is
halogen, CN, OH, SH, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-C6-alkylthio- Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, Ci- C6-alkylthiocarbonyloxy or a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, Ci- C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci- C4-alkyl, NH2, (Ci-C6-alkyl)amino or di(Ci-C6-alkyl)amino,
preferably which heteroaryl is selected from the group consisting of X1 to X9:
Figure imgf000027_0001
X1 X2 X3
Figure imgf000028_0001
Figure imgf000028_0002
X7 X8 X9
where the arrow indicates the point of attachment and wherein R6 to R9 independently of one another are hydrogen, halogen, CN, NO2, C1-C6- alkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxy- carbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino or di(Ci-C6- alkyl)amino; particularly preferred halogen, OH, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci- C6-alkoxycarbonyl-Ci-C6-alkoxy or a 5-membered heteroaryl having 2 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino;
preferably which heteroaryl is selected from the group consisting of X2 to X8:
Figure imgf000028_0003
Figure imgf000029_0001
X8 where the arrow indicates the point of attachment and wherein R6 to R9 independently of one another are hydrogen, halogen, CN, NO2, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthio- carbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4- alkyl)amino; especially preferred halogen, OH, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci- C4-alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 2 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino,
preferably which heteroaryl is selected from the group consisting of X2 to X8:
Figure imgf000029_0002
Figure imgf000030_0001
X8 where the arrow indicates the point of attachment and wherein R6 to R9 independently of one another are hydrogen, halogen, CN, NO2, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthio- carbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4- alkyl)amino; more preferred halogen, OH, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 3 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino,
preferably which heteroaryl is selected from the group consisting of X4 to
Figure imgf000030_0002
where the arrow indicates the point of attachment and wherein R6 to R9 independently of one another are hydrogen, halogen, CN, NO2, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthio- carbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxyl- carbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino.
Also preferred are the triazines of formula I, wherein R2 is
halogen, CN, OH, SH, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-C6-alkylthio- Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, Ci-
C6-alkylthiocarbonyloxy or a 5-membered heteroaryl having 1 to 4 nitrogen atoms, which heteroaryl is attached to the triazine ring via a nitrogen atom and is unsubstituted,
preferably which heteroaryl is selected from the group consisting of X1 to X9 as mentioned above, wherein R6 to R9 are hydrogen; particularly preferred halogen, OH, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci- C6-alkoxycarbonyl-Ci-C6-alkoxy or a 5-membered heteroaryl having 2 to 4 nitrogen
atoms, which heteroaryl is attached to the triazine ring via a nitrogen atom and is unsubstituted,
preferably which heteroaryl is selected from the group consisting of X2 to X8 as mentioned above, wherein R6 to R9 are hydrogen; especially preferred halogen, OH , Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci- C4-alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 2 to 4 nitrogen
atoms, which heteroaryl is attached to the triazine ring via a nitrogen atom and is unsubstituted
preferably which heteroaryl is selected from the group consisting of X2 to X8 as mentioned above, wherein R6 to R9 are hydrogen; more preferred halogen, OH, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 3 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom and is unsubstituted,
preferably which heteroaryl is selected from the group consisting of X4 to X7 as mentioned above, wherein R6 to R9 are hydrogen. Also preferred are the triazines of formula I, wherein R2 is
halogen, CN , OH, SH, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-C6-alkylthio- Ci-C4-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, Ci- C6-alkylthiocarbonyloxy or a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-alkoxy, C1-C6- alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci- C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, C1-C6- alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-
C6-alkyl)amino or di(Ci-C6-alkyl)amino, preferably which heteroaryl is selected from the group consisting of X1 to X9 as mentioned above, wherein the arrow indicates the point of attachment and wherein R6 to R9 independently of one another are halogen, CN, N02, Ci-C6-alkyl, Ci-C6-alkoxy, d-C6-alkylthio, Ci-C6- alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, C1-C6- alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl- Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino or di(Ci-C6-alkyl)amino; particularly preferred halogen, OH, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-
C6-alkoxycarbonyl-Ci-C6-alkoxy or a 5-membered heteroaryl having 2 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci- C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino, preferably which heteroaryl is selected from the group consisting of X2 to
X8 as mentioned above, wherein the arrow indicates the point of attachment and wherein R6 to R9 independently of one another are halogen, CN, N02, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, C1-C4- alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (C1-C4- alkyl)amino or di(Ci-C4-alkyl)amino; especially preferred halogen, OH, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, Ci- C4-alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 2 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci- C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2,
(Ci-C4-alkyl)amino or di(Ci-C4-alkyl)amino; preferably which heteroaryl is selected from the group consisting of X2 to X8 as mentioned above, wherein the arrow indicates the point of attachment and wherein R6 to R9 independently of one another are halogen, CN, N02, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, C1-C4- alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (C1-C4- alkyl)amino or di(Ci-C4-alkyl)amino; more preferred halogen, OH, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy, C1-C4- alkoxycarbonyl-Ci-C4-alkoxy or a 5-membered heteroaryl having 3 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is substituted by 1 to 3 substituents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, Ci-C4-alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (C1-C4- alkyl)amino or di(Ci-C4-alkyl)amino, preferably which heteroaryl is selected from the group consisting of X4 to X7 as mentioned above, wherein where the arrow indicates the point of attachment and wherein R6 to R9 independently of one another are halogen, CN, N02, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-alkylthio, C1-C4- alkoxycarbonyl, Ci-C4-alkylthiocarbonyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, NH2, (C1-C4- alkyl)amino or di(Ci-C4-alkyl)amino.
Preferred are the triazines of formula I, wherein R3, R4 and R5 independently of one another are
hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci-C4- alkyl)amino; particularly preferred hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(C C4-alkyl)amino.
Also preferred are the triazines of formula I, wherein R3 is hydrogen, and R4 and R5 independently of one another are
hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci-C4- alkyl)amino; particularly preferred hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(C C4-alkyl)amino. Also preferred are the triazines of formula I, wherein R4 is hydrogen, and R3 and R5 independently of one another are
hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci-C4- alkyl)amino; particularly preferred hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci- C4-alkyl)amino.
Also preferred are the triazines of formula I, wherein R3 and R4 are hydrogen, and R5 is hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci-C4- alkyl)amino; particularly preferred hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci- C4-alkyl)amino.
Also preferred are the triazines of formula I, wherein R3 and R5 are hydrogen, and R4 is hydrogen, halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci-C4- alkyl)amino; particularly preferred hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl and di(Ci- C4-alkyl)amino.
Particular preference is given to triazines of the formula I. a (corresponds to formula I wherein R3, R4 and R5 are hydrogen),
Figure imgf000034_0001
wherein the variables R1 and R2 have the meanings, in particular the preferred meanings, as defined above; most preference is given to the compounds of the formulae l.a.1 to l.a.294 of Table 1 , where the definitions of the variables R1 and R2 are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own:
Table 1
Figure imgf000035_0001
Figure imgf000036_0001
Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Also preferred are the triazines of formula l.b, particularly preferred the triazines of formulae l.b.1 to l.b.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3 is F:
Figure imgf000046_0001
Also preferred are the triazines of formula l.c, particularly preferred the triazines of formulae l.c.1 to l.c.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3
Figure imgf000046_0002
Also preferred are the triazines of formula l.d, particularly preferred the triazines of formulae l.d.1 to l.d.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3
Figure imgf000046_0003
Also preferred are the triazines of formula l.e, particularly preferred the triazines of formulae l.e.1 to l.e.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3
Figure imgf000046_0004
Also preferred are the triazines of formula l.f, particularly preferred the triazines of formulae l.f.1 to l.f.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3
Figure imgf000046_0005
Also preferred are the triazines of formula l.g, particularly preferred the triazines of formulae l.g.1 to l.g.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3
Figure imgf000047_0001
Also preferred are the triazines of formula I.h, particularly preferred the triazines of formulae I.h.1 to l.h.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3
Figure imgf000047_0002
Also preferred are the triazines of formula l.i, particularly preferred the triazines of formulae l.i.1 to l.i.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3
Figure imgf000047_0003
Also preferred are the triazines of formula l.k, particularly preferred the triazines of formulae l.k.1 to l.k.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3
Figure imgf000047_0004
Also preferred are the triazines of formula I.I, particularly preferred the triazines of formulae 1.1.1 to 1.1.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R3 is N(CH3)2:
Figure imgf000048_0001
Also preferred are the triazines of formula l.m, particularly preferred the triazines of formulae l.m.1 to l.m.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in th 4 is F:
Figure imgf000048_0002
Also preferred are the triazines of formula l.n, particularly preferred the triazines of formulae l.n.1 to l.n.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R4
Figure imgf000048_0003
Also preferred are the triazines of formula l.o, particularly preferred the triazines of formulae 1.0.1 to I.O.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R4
Figure imgf000048_0004
Also preferred are the triazines of formula l.p, particularly preferred the triazines of formulae l.p.1 to l.p.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R4
Figure imgf000048_0005
Also preferred are the triazines of formula l.q, particularly preferred the triazines of formulae l.q.1 to l.q.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R4
Figure imgf000049_0001
Also preferred are the triazines of formula l.r, particularly preferred the triazines of formulae l.r.1 to l.r.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R4
Figure imgf000049_0002
Also preferred are the triazines of formula l.s, particularly preferred the triazines of formulae l.s.1 to l.s.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R4
Figure imgf000049_0003
Also preferred are the triazines of formula l.t, particularly preferred the triazines of formulae l.t.1 to l.t.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R4
Figure imgf000049_0004
Also preferred are the triazines of formula l.u, particularly preferred the triazines of formulae l.u.1 to l.u.420, which differ from the corresponding triazines of formulae l.a.1 to l.a.420 only in that R4 is S02CH3:
Figure imgf000050_0001
Also preferred are the triazines of formula l.v, particularly preferred the triazines of formulae l.v.1 to l.v.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R4 is N(CH3)2:
Figure imgf000050_0002
Also preferred are the triazines of formula l.v, particularly preferred the triazines of formulae l.w.1 to l.w.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R3 and R4 are CH3:
Figure imgf000050_0003
Also preferred are the triazines of formula l.v, particularly preferred the triazines of formulae l.x.1 to l.x.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R3
Figure imgf000050_0004
Also preferred are the triazines of formula l.v, particularly preferred the triazines of formulae l.y.1 to l.y.420, which differ from the corresponding triazines of formulae I. to l.a.420 only in that R4 is Br:
Figure imgf000050_0005
The triazines of formula I according to the invention can be prepared by standard processes of organic chemistry, for example by the following processes: Process A)
The triazines of formula I wherein R2 is hydroxy can be prepared by reaction of keto co
Figure imgf000051_0001
I, wherein
Y stands for R2 which is hydroxy L1 stand for a nucleophilically displaceable leaving group such as hydroxy, C1-C6- alkoxy or benzyloxy, wherein the benzyl ring might be substituted by one to five nitro groups; preferably is hydroxy, Ci-C6-alkoxy or 4-N02-benzyloxy, particularly preferred is hydroxyl or Ci-C6-alkoxy, especially preferred is hydroxy or methoxy. The cyclisation of keto-compounds of formula II with amidrazones of formula III is usually carried out at temperature from 0 °C to the boiling point of the reaction mixture, preferably at temperature from 0 °C to 300 °C, particularly preferably at temperature from 10 °C to 200 °C, in an inert organic solvent (e.g. Journal of Organic Chemistry 1987, 52(19), 4287-92).
Suitable solvents are aromatic hydrocarbons such as tolene, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert. -butyl methyl- ether, dioxane, anisole and tetrahydrofuran, alkoholes such as methanol, ethanol, n- propanol, isopropanol, n-butanol and tert.-butanol. Particular preference is given to toluene, ethanol and iso-butanol.
It is also possible to use mixtures of the solvents mentioned.
Starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use either an excess of the keto compounds of formula II or of the amidrazones of formula III. Preferably the keto compounds of formula II and the amidrazones of formula III are used in equimolar amounts.
The reaction mixtures are worked up in a customary manner, for example by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product. Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately elevated temperature.
If the intermediates and the end products are obtained as solid, purification can also be carried out by recrystallisation or digestion.
Process B)
The triazines of formula I wherein R2 is hydroxy in train can be reacted with
electrophiles of formula IV to give triazines of formula I wherein R2 is Ci-C6-alkoxy- carbonyloxy, Ci-C6-alkylthiocarbonyloxy, di(Ci-C6-alkyl)aminocarbonyloxy:
Figure imgf000052_0001
I, wherein IV I, wherein
Y stands for R2 which is hydroxy Y stands for R2 which is
CrC6-alkoxycarbonyloxy,
Ci-C6-alkylthiocarbonyloxy or di(Ci-C6-alkyl)aminocarbonyloxy RA in formula IV stands for Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl or di(Ci-C6- alkyl)aminocarbonyl.
L2 in formula IV stands for a nucleophilically displaceable leaving group such as halogen, Ci-C6-alkoxy, Ci-C6-alkylcarbonyloxy, Ci-C6-alkoxycarbonyloxy, C1-C6- haloalkylcarbonyloxy, Ci-C6-haloalkoxycarbonyloxy Ci-C6-alkylsulfonyloxy, C1-C6- haloalkylsulfonyloxy, arylsulfonyloxy. Preferably L2 is halogen, particularly preferred CI.
Especially preferred electrophiles of formula IV are 0-(Ci-C6-alkyl)-chloridocarbonates, S-(Ci-C6-alkyl)-chloridothiocarbonates and N,N-di(Ci-C6-alkyl)carbamoyl chlorides.
The reaction of triazines of formula I, wherein R2 is hydroxyl, with electrophiles of formula IV is usually carried out at from -78 °C to the boiling point of the reaction mixture, preferably at from -78°C to100°C, particularly preferably at from -20°C to 40°C, in an inert organic solvent in the presence of a base (e.g. Tetrahedron 2010, 66, 7544-
7561 ).
The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use an excess of the electrophile of formula IV. Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons such as tolene, o-, m- and p- xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert- butyl methylether, dioxane, anisole and tetrahydrofuran, as well as dimethylformamide and Ν,Ν-dimethylacetamide or N.methylpyrrolidone. Particular preference is given to dichloromethane and tetrahydrofuran.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, inorganic compounds such as 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, and furthermore organic bases, such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and 4-dimethylaminopyridine and also bicyclic amines. Particular preference is given to triethylamine,
diisopropylethylamine, pyridine and 4-dimethylaminopyridine. The bases are generally employed in equimolar amounts, however they can also be employed in catalytic amounts, in excess or, if appropriate, be used as solvent.
Work up can be carried out in a known manner.
Process C)
The triazines of formula I wherein R2 is hydroxy in train can also be reacted with isocyanates of formula V to give triazines of formula I wherein R2 is aminocarbonyloxy or (Ci-C6-alkyl)aminocarbonyloxy:
Figure imgf000053_0001
V I, wherein
l.where h Y stands for R2 which is
■ ~ 2 aminocarbonyloxy or
(Ci-C6-alkyl)aminocarbonyloxy RB in formula V stands for SOC or Ci-C6-alkyl.
Particularly preferred isocyanates of formula V are sulfuryl chloride isocyanate and N- (Ci -C6-a I kyl) i socya nates . The reaction of triazines of formula I with the isocyanates of formula V is usually carried out at from -78 °C to the boiling point of the reaction mixture, preferably at from 0°C to100°C, particularly preferably at from room temperature °C to 100°C, in an inert organic solvent (e.g. J. Med. Chem. 201 1 , 54, 4324-4338; WO 07/123892).
Starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use an excess of the isocyanate V.
Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons such as tolene, o-, m- and p- xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert- butyl methylether, dioxane, anisole and tetrahydrofuran, as well as dimethylformamide and Ν,Ν-dimethylacetamide or N.methylpyrrolidone. Particular preference is given to dichloromethane and tetrahydrofuran.
It is also possible to use mixtures of the solvents mentioned.
Work up can be carried out in a known manner.
Process D)
The triazines of formula I wherein R2 is hydroxy in train can also be reacted with a halogenating agent to give triazines of formula I wherein R2 is halogen:
Figure imgf000054_0001
Y s lands for R wh bh B hyd roxy
The reaction of the triazines of formula I wherein R2 is hydroxy with the halogenating agent IV is usually carried out at from -78°C to the boiling point of the reaction mixture, preferably at from 0°C to 200°C, particularly preferably at from 0°C to 80°C optionally in an inert organic solvent, optionally in the presence of a base (e.g. Liebigs Ann. Chem. 1990, 631 -40).
Suitable halogenating agents are e.g. POCI3, POBr3, PCI3, PBr3, PCI5, PBr5, SOC , SOBr2, oxalyl chloride, phosgene, diphosgene and triphosgen. Preferred halogenating agents are POCI3, POBr3, SOC and oxalyl chloride. Particularly preferred is POCI3. Preferably the reaction is carried out in the presence of a base. Suitable bases are arylamines such as dimethylaniline. The reactants can be reacted with one another as such, that is to say without any additional solvent. However, it is advantageous to add an inert solvent or mixtures thereof.
Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert. -butyl methylether, dioxane, anisole and tetrahydrofuran. Particular preference is given to dichloromethane, chloroform and tetrahydrofuran. It is also possible to use mixtures of the solvents mentioned.
Work up can be carried out in a known manner. Process E)
The triazines of formula I wherein R2 is halogen in train can be reacted with
nucleophiles of formula VI to give triazines of formula I wherein
R2 is CN, SH, Ci-Ce-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-C6-alkoxy- Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkyltio-Ci-C4-alkylthio, Ci-C6- alkoxycarbonyl-Ci-C6-alkoxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C1-C6- haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, C1-C6- alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci-
C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, C1-C6- alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci- C6-alkyl)amino or di(Ci-C6-alkyl)amino,
phenoxy or phenyl-Ci-C4-alkoxy,
which phenyls are unsubstituted or substituted by one to five substit-uents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-haloalkyl, Ci-C4-haloalkoxy:
Figure imgf000056_0001
koxy- 0-C4-alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio,
Ci-C6-alkylthio-CrC4-alkoxy, Ci-C6-alkylthio- Ci -C4-al ky I th i o , C 1 -C6-al koxycarbonyl-Ci -C6-al ky oxy , a five membered heteroaryl having 1 to 4 N-atoms, phenoxy or phenyl-Ci-C4-alkoxy
Rc in formula VI stands for CN, SH, Ci-C6-alkoxy, d-Ce-alkylthio, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkyltio-Ci-C4- alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms, which heteroaryl is attached to the triazine ring via a nitrogen atom
and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C1-C6- haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, C1-C6- alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci-
C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, C1-C6- alkoxycarbonyl-Ci-C4-alkyl, Ci-C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci- C6-alkyl)amino or di(Ci-C6-alkyl)amino,
phenoxy or phenyl-Ci-C4-alkoxy,
which phenyls are unsubstituted or substituted by one to five substit-uents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
The reaction of triazines of formula I wherein R2 is halogen with nucleophiles of formula VI is usually carried out at from -78 °C to the boiling point of the reaction mixture, preferably at from -78°C to100°C, particularly preferably at from 0°C to 80°C, in an inert organic solvent in the presence of a base (e.g. J. Org. Chem. 1987, 52 (19), 4287- 4292). The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use an excess of the nuceophile of formula VI.
Suitable solvents are aromatic hydrocarbons such as tolene, 0-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert. -butyl methylether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, as well as dimethylsulfoxide, dimethylformamide and N,N-dimethylacet- amide or N-methylpyrrolidone. Particular preference is given to tetrahydrofuran and dimethylformamide.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general inorganic compounds such as alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, and furthermore organic bases, such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and 4- dimethylaminopyridine and also bicyclic amines. Particular preference is given to sodium hydride, triethylamine and 4-dimethylaminopyridine.
The bases are generally employed in equimolar amounts, however they can also be employed in catalytic amounts, in excess or, if appropriate, be used as solvent.
Work up can be carried out in a known manner.
The keto compounds of formula II required for the preparation of the triazines of formula I wherein R2 is hydroxy are known from the literature (e.g. Org. Lett. 2010, 12, 2864-2867, Org. Lett. 2010, 12, 4424-4427). They can be prepared in accordance with the literature cited and/or are commercially available.
The amidrazones of formula III required for the preparation of the triazines of formula I wherein R2 is hydroxy are known from the literature (e.g. Russian Chemical Bulletin 2010, 59, 1808-1816; Org. Lett. 2007, 9, 171 1 -1714). They can be prepared in accordance with the literature cited and/or are commercially available.
The electrophiles of formula IV required for the preparation of the triazines of formula I wherein R2 is Ci-C6-alkoxycarbonyloxy, Ci-C6-alkylthiocarbonyloxy or di(Ci-C6- alkyl)aminocarbonyloxy are commercially available. The isocyanates of formula V required for the preparation of triazines of formula I wherein R2 is aminocarbonyloxy or (Ci-C6-alkyl)aminocarbonyloxy are commercially available.
The nucleophils of formula VI required for the preparation of triazines of formula I wherein R2 is CN, SH, Ci-C6-alkoxy, d-Ce-alkylthio, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-C6- alkoxy-Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkyltio-Ci-C4-alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms, which heteroaryl is attached to the triazine ring via a nitrogen atom and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, Ci-C6-haloalkyl, C2- C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C1-C6- alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio- Ci-C4-alkyl, hydroxycarbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, Ci- C6-alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino or di(Ci-C6-alkyl)amino phenoxy or phenyl-Ci-C4-alkoxy,
which phenyls are unsubstituted or substituted by one to five substit-uents selected from the group consisting of halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- haloalkyl and Ci-C4-haloalkoxy
are commercially available. The triazines I and compositions comprising them are suitable as herbicides. They are suitable as such or as an appropriately formulated composition.
The herbicidal compositions comprising the triazines of formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
Depending on the application method in question, the triazines I or compositions comprising them can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. Preferred crops are the following: Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max,
Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
The triazines of formula I according to the invention can also be used in genetically modified plants. The term " genetically modified plants" is to be understood as plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species' genome or to exhibit a deletion of DNA that was native to that species' genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone. Often, a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recombinant DNA technique. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or
polypeptides, e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment. Plants that have been modified by breeding, mutagenesis or genetic engineering, e.g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvyl shikimate 3- phosphate synthase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid
biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering; furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are, for example, described in Pest Management Science 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of
Agricultural Research 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by mutgenesis and conventional methods of breeding, e. g., Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g., imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g., tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate, imidazolinones and glufosinate, some of which are under development or commercially available under the brands or trade names RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany). Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g., VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g., Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins;
proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize- RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3- hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g., WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g., in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles
(Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the Cry1 Ab toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin);
NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e. g., Agrisure® CB) and Bt176 from
Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from
Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme). Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called " pathogenesis-related proteins" (PR proteins, see, e.g., EP-A 392 225), plant disease resistance genes (e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato, Solanum bulbocastanum) or T4-lyso-zym (e.g., potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora). The methods for producing such genetically modi-fied plants are generally known to the person skilled in the art and are described, e.g., in the publications mentioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada). Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
Furthermore, it has been found that the triazines of the formula I according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard, compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for desiccating and/or defoliating plants using the triazines of the formula I have been found. As desiccants, the triazines of the formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants. Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pernicious fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.
Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting. The invention also relates to agrochemical compositions comprising an auxiliary and at least one triazine of formula I according to the invention.
The agrochemical composition comprises a pesticidally effective amount of a c triazine of formula I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic conditions and the specific triazine of formula I used.
The triazine of formula I, their agriculturally acceptable salts or derivatives, provided that the triazines of formula I have a carboxyl group, can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for agrochemical composition types 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, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further agrochemical compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti- foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof. Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in
McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.). Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes,
sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines.
Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or
polyethyleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5. Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives such as
alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin. Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for agrochemical composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a triazine of formula I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The active substance dissolves upon dilution with water. ii) Dispersible concentrates (DC)
5-25 wt% of a triazine of formula I according to the invention and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a triazine of formula I according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic
hydrocarbon). Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a triazine of formula I according to the invention and 1 -10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a triazine of formula I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a triazine of formula I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a triazine of formula I according to the invention are ground in a rotor- stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
iv) Microemulsion (ME)
5-20 wt% of a triazine of formula I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
iv) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a triazine of formula I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a triazine of formula I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g.
hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.
ix) Dustable powders (DP, DS)
1 -10 wt% of a triazine of formula I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
x) Granules (GR, FG) 0.5-30 wt% of a triazine of formula I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
xi) Ultra-low volume liquids (UL)
1 -50 wt% of a triazine of formula I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
The agrochemical compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1 -1 wt% colorants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Water-soluble concentrates (LS), Suspoemulsions (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 usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying or treating triazine of formula I and
compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, triazine of formula I or the agrochemical compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, in particular from 0.1 to 0.75 kg per ha.
In another preferred embodiment of the invention, the rates of application of the triazines of formula I according to the present invention (total amount of triazine I) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage. In another preferred embodiment of the invention, the application rates of the triazine of formula I are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha of active substance (a.s.). In another preferred embodiment of the invention, the application rate of the triazine of formula I is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha, of active substance.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seed) are generally required.
In another preferrerd ambodiment of the invention, to treat the seed, the triazines I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material. Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
The user applies the agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
In a further embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g.
components comprising triazine of formula I and/or optionally other presticides, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
In a further embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g.
components comprising triazine of formula I and/or optionally other presticides can be applied jointly (e.g. after tank mix) or consecutively.
The triazines of the formula I or the compositions comprising them can be applied pre-, post-emergence or pre-plant, or together with the seed of a crop plant. It is also possible to apply the herbicidal composition or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesirable plants growing underneath, or the bare soil surface (post- directed, lay-by).
In a further embodiment, the triazines of the formula I or the compositions comprising them can be applied by treating seed. The treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the triazine of the formula I according to the invention or the compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.
The term "seed" comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
To widen the spectrum of action and to achieve synergistic effects, the triazines of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active ingredient groups and then applied concomitantly. Suitable components for mixtures are, for example herbicides from the classes of the
acetamides, amides, aryloxyphenoxypropionat.es, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chloro- carboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenyl- carbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoroamidates, phosphorodithioates, phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimi- dinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylamino- carbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolo- pyrimidines, triketones, uracils, ureas.
It may furthermore be beneficial to apply the triazines of the formula I alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or
phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.
Moreover, it may be useful to apply the triazines of the formula I in combination with safeners. Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the triazines of the formula I towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post- emergence application of the useful plant. The safeners and the triazines of the formula I can be applied simultaneously or in succession.
Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H-1 ,2,4- triazol-3-carboxylic acids, 1 -phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha- oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4- (aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4- (haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenyl- carbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.
The following examples serve to illustrate the invention. A Preparation examples
Example 1 : 6-lsobutyl-3-pyrimidin-2-yl[1 ,2,4]triazin-5-ol
Figure imgf000070_0001
Step 1 : To a solution of pyrimidine-2-carbonitrile (5.00 g, 47.6 mmol) in ethanol (50 ml) was added hydrazine hydrate (2.31 ml, 47.6 mmol). The resulting solution was stirred at 75°C for four hours. The mixture was subsequently concentrated in vacuum to give crude N' -aminopyrimidine-2-carboxamide (6.46 g, 99 %) as a yellow syrup, which was used directly in step 2 without further purification. Step 2: To a solution of N' -aminopyrimidine-2-carboxamidine in ethanol (50 ml) was added 4-methyl-2-oxo-pentanoic acid (7.43 g, 57.1 mmol). The resulting solution was stirred at 75°C for sixteen hours and subsequently concentrated in vacuum. The obtained orange solid was suspended in diethylether, stirred for sixteen hours and filtered. The obtained solid was dried in a vacuum oven (40°C, 10 mbar) to give 9.22 g (83.8 %) of the title compound as yellow solid.
H-NMR (CDCIs): δ = 1.00 (d, 6H); 2.29 (sept, 1 H); 2.75 (d, 2H); 7.60 (t, 1 H); 9.00 (d, 2H). Example 2: 5-Chloro-6-isobutyl-3-pyrimidin-2-yl[1 ,2,4]triazine
Figure imgf000071_0001
To a solution of 6-isobutyl-3-pyrimidin-2-yl[1 ,2,4]triazin-5-ol (30.0 g, 130 mmol) in phosphorus oxychloride (270 ml) was added N,N-dimethylanilin (16.4 ml, 130 mmol). The reaction mixture was stirred for 64 hours at 23°C and subsequently concentrated in vacuum. The residue was dissolved in dichloromethane and washed with water, 10% aqueous ammonia solution and brine. The organic phase was dried and concentrated in vacuum. The residue was purified by column (Cyclohexane/EtOAc: 1/2) to give 15.0 g (46.3%) of the title compound as slightly yellow solid.
H-NMR (DMSO): δ = 0.94 (d, 6H); 2.16 (sept, 1 H); 2.54 (d, 2H); 7.81 (t, 1 H); 9.10 (d, 2H).
Example 3: 5-lmidazol-1 -yl- ,2,4]triazine
Figure imgf000071_0002
To a suspension of 5-chloro-6-isobutyl-3-pyrimidin-2-yl[1 ,2,4]triazine (400 mg, 1.60 mmol) in toluene was added imidazole (229 mg, 3.36 mmol). The resulting reaction mixture was stirred at 23°C for three hours. Water was added, the biphasic mixture was stirred for five minutes and the phases were separated. The organic phase was washed twice with brine, dried and concentrated to a suspension. The precipated solid was filtered and dried to give 204 mg (45.3%) of the title compound as slightly yellow oil.
H-NMR (DMSO): δ = 0.9 (d, 6H); 2.1 (sept, 1 H); 3.2 (d, 2H); 7.2 (s, 1 H); 7.8 (t, 1 H); 7.9 (s, 1 H); 8.4 (s, 1 H); 9.1 (d, 2H).
Example 4: 6-lsobutyl-3-pyrimidin-2-yl[1 ,2,4]triazin-5-yl-carbonic acid isopropyl ester
Figure imgf000072_0001
To a solution of 6-isobutyl-3-pyrimidin-2-yl[1 ,2,4]triazin-5-ol (500 mg, 2.16 mmol) and triethylamine (0.300 ml, 2.16 mmol) in dichloromethane was added at 0°C a solution of isopropyl chloroformate in toluene (1.00 M, 6.49 ml). The resulting solution was stirred for sixteen hours at 0°C. The reaction mixture was transferred in a separating funnel filled with an aqueous 5% sodium bicarbonate solution, extracted, the phases were separated and the organic phase was washed with water, dried and concentrated in vacuum. The residue was purified by column (dichloromethane/methanol: 98/2) to give 60.0 mg (8.89%) of the title compound as slightly yellow oil.
H-NMR (CDCIs): δ = 1.01 (d, 6H); 1 .19 (d, 6H); 2.27 (sept, 1 H); 2.71 (d, 2H); 5.01 (sept, 1 H); 7.50 (t, 1 H); 8.90 (d, 2H).
The triazines of formula la listed in table 2 and of formula I listed in table 3 below were prepared analogously.
Figure imgf000073_0001
Figure imgf000074_0001
LCMS,
R R2
[M+H]+
.a.470 CH2CH(CH3)2 4-CF3-(imidazol-1 -yl) 350
.a.471 CH2CH(CH3)2 3-N02-(1 ,2,4-triazol-1 -yl) 328
.a.472 CH2CH(CH3)2 2-CH2CH3-(imidazol-1 -yl) 310
.a.473 CH2CH(CH3)2 4-CN-(imidazol-1 -yl) 307
.a.474 CH2CH(CH3)2 3-CF3-(pyrazol-1 -yl) 350
.a.475 CH2CH(CH3)2 2-CH2C(0)OCH3-(imidazol-1 -yl) 355
.a.476 CH2CH(CH3)2 OCH(CH3)2 274
.a.477 CH2CH(CH3)2 2-C(0)OCH2CH3-(imidazol-1 -yl) 354
.a.478 CH2CH(CH3)2 3-CF3-(1 ,2,4-triazol-1 -yl) 351
.a.479 CH2CH2CH=CH2 OCH(CH3)2 272
.a.480 CH2CH2CH=CH2 3-C(0)OCH3-(1 ,2,4-triazol-1 -yl) 339
.a.481 CH2CH2CH=CH2 3-CN-(1 ,2,4-triazol-1 -yl) 306
.a.482 CH2CH2CH=CH2 3-SCH3-(1 ,2,4-triazol-1 -yl) 327
.a.483 CH2CH2CH=CH2 3-CF3-(1 ,2,4-triazol-1 -yl) 349
.a.484 CH2CH2CH=CH2 OCH2-(2-OCH3-C6H4) 351
.a.485 CH2CH2CH=CH2 OCH2-(4-OCH3-C6H4) 350
.a.486 CH2CH2CH=CH2 OCH2-(2,3-diOCH3-C6H3) 380
.a.487 CH2CH2CH=CH2 OCH2-(2,5-diOCH3-C6H3) 381
.a.488 CH2CH2CH=CH2 OCH2-(3,4-diOCH3-C6H3) 381
.a.489 CH2CH2C(0)OCH3 OH 262
.a.490 CH2CH(CH3)2 CH(CN)2 280
.a.491 CH2CH(CH3)2 NC(0)C(CH3)3 315
.a.492 CH2CH(CH3)2 C(0)CH3 258
Figure imgf000075_0001
Table 3
LCMS,
R R2 R3 R4 R5
[M+H]+ l.d.48 CH2CH(CH3)2 OH CH3 H H 246 l.g.48 CH2CH(CH3)2 OH OCH3 H H 262
I.0.48 CH2CH(CH3)2 OH H CH3 H 246 l.r.48 CH2CH(CH3)2 OH H OCH3 H 262 l.w.48 CH2CH(CH3)2 OH CH3 CH3 H 260 l.y.48 CH2CH(CH3)2 OH H Br H 31 1 l.d.51 CH2CH2CH=CH2 OH CHs H H 244
1.0.51 CH2CH2CH=CH2 OH H CHs H 244
Part B: Use examples
The herbicidal action of the compounds and compositions according to the invention was demonstrated by the following greenhouse experiments:
The culture containers used were plastic pots containing loamy sand with
approximately 3.0% of humus as substrate. The seeds of the test plants were sown separately for each species.
For the pre-emergence treatment, the active compounds, suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants unless this was adversely affected by the active compounds.
For the post-emergence treatment, the test plants were grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. To this end, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
Depending on the species, the plants were kept at 10 - 25°C and 20 - 35°C, respectively. The test period extended over 2 to 4 weeks. During this time, the plants were tended and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage or normal course of growth. Good herbicidal activity is given at values of at least 70, and very good herbicidal activity is given at values of at least 85.
The respective stated components A and B, and if appropriate, C were formulated as a 10% by weight strength emulsion concentrate and, with addition of the amount of solvent system, introduced into the spray liquor used for applying the active compound. In the examples, the solvent used was water.
The test period extended over 20 and 21 days, respectively. During this time, the plants were tended, and their reaction to the treatment with active compound was monitored.
In the examples below, using the method of S. R. Colby (1967) "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, p. 22ff., the value E, which is expected if the activity of the individual active compounds is only additive, was calculated. Ε = Χ + Υ - (ΧΎ/100)
where
X = percent activity using active compound A at an application rate a;
Y = percent activity using active compound B at an application rate b;
E = expected activity (in %) by A + B at application rates a + b.
If the value found experimentally is higher than the value E calculated according to Colby, a synergistic effect is present.
The plants used in the greenhouse experiments were of the following species:
Figure imgf000077_0001
The results of these tests are given below in the use examples and demonstrate the synergistic effect of the triazines of formula I. In this context, " a.s." means active substance, based on 100 % active ingredient.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
At an application rate of 3000 g/ha, the compounds I. a.43, I. a.44, I. a.46 and I. a.45 applied by the post-emergence method, showed very good herbicidal activity against Abutilon theophrasti and Setaria faberi. At an application rate of 1000 g/ha, the compounds I. a.422 wherein R1 is (Chb^CHs and R2 is OH, l.a.428 wherein R is CH2CH(CH3)CH2CH2CH3 and R2 is OH, l.a.51 , I. a.58 and I. a.132 applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus and Chenopodium album.
At an application rate of 2000 g/ha, the compound I. a.434 wherein R1 is C(CHs)3 and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Matricaria inodora and at an application rate of 3000 g/ha good herbicidal activity against Abutilon theophrasti and Setaria faberi.
At an application rate of 515 g/ha, the compound l.a.432 wherein R1 is CH(C2H5)2 and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album, Polygonum convolvulus and Setaria viridis.
At an application rate of 925 g/ha, the compound I. a.47 applied by the post-emergence method, showed very good herbicidal activity against Alopercurus myosuroides, Amaranthus retroflexus, Polygonum convolvulus and Setaria viridis. At an application rate of 3000 g/ha, the compounds I. a.48 and l.a.441 wherein R1 is cyclohexyl and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Abutilon theophrasti.
At an application rate of 341 g/ha, the compound l.a.426 wherein R1 is
CH2CH(CH3)CH2CH3 and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
At an application rate of 509 g/ha, the compound l.a.424 wherein R1 is
CH2CH2CH(CH3)2 and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
At an application rate of 1000 g/ha, the compound I. a.423 wherein R1 is
CH2CH2CH2CH(CH3)2 and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
At an application rate of 670 g/ha, the compound l.a.427 wherein R1 is CH2CH(C2H5)2 and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis. At an application rate of 482 g/ha, the compound l.a.430 wherein R1 CH2CH(CH3)CH(CH3)2 is and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album and Polygonum convolvulus.
At an application rate of 1000 g/ha, the compounds I. a.71 and l.a.453 wherein R1 is CH2CH2SCH3 and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album and Galium aperine.
At an application rate of 582 g/ha, the compound l.a.442 wherein R1 is CH2-cyclobutyl and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis. At an application rate of 926 g/ha, the compound l.a.443 wherein R1 is CH2-cyclopentyl and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Polygonum convolvulus and Setaria viridis.
At an application rate of 443 g/ha, the compound l.a.444 wherein R1 is CH2-cyclohexyl and R2 is OH applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album, Polygonum convolvulus and Galium aperine.
At an application rate of 741 g/ha, the compound l.y.48 wherein R1 is CH2CH(CH3)2, R2 is OH, R3 and R5 are H and R4 is Br applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album and good herbicidal activity against Polygonum convolvulus.
At an application rate of 1000 g/ha, the compounds I. a.421 wherein R1 is (CH2)4CH3 and R2 is OH, l.a.425 wherein R1 is CH2CH2C(CH3)3 and R2 is OH, l.a.79, l.a.76, l.d.48, l.g.48, 1.0.48 and l.r.48 applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album and Polygonum convolvulus.
At an application rate of 3000 g/ha compound I. a.48 applied by the post-emergence method, showed very good herbicidal activity against Alopercurus myosuroides and Setaria viridis.
At an application rate of 3000 g/ha compound I. a.44 applied by the post-emergence method, showed very good herbicidal activity against Avena fatua and Setaria faberi. At an application rate of 3000 g/ha compound I. a.441 applied by the post-emergence method, showed good herbicidal activity against Avena fatua and Setaria faberi.
At an application rate of 3000 g/ha compound I. a.44 applied by the post-emergence method, showed very good herbicidal activity against Avena fatua.
At an application rate of 2000 g/ha compound l.a.450 applied by the post-emergence method, showed very good herbicidal activity against Matricaria inodora and good herbicidal activity against Agrostis stolonifera.
At an application rate of 500 g/ha the compounds l.a.468 and l.a.485 applied by the post-emergence method, showed very good herbicidal activity against Echinocloa crus- galli, Polygonum convolvulus and Setaria viridis. At an application rate of 500 g/ha compound l.a.484, at an application rate of 798 g/ha compound I. a.459 and at an application rate of 1000 g/ha compound I. a.71 applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus, Echinocloa crus-galli and Setaria viridis. At an application rate of 145 g/ha compound I. a.429, at an application rate of 321 g/ha compound I. a.451 and at an application rate of 1000 g/ha compound I. a.455 applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus and Chenopodium album. At an application rate of 500 g/ha compound l.a.486 and at an application rate of 1000 g/ha the compounds I. a.132, I. a.446, l.a.472 and l.d.48 applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus,
Polygonum convolvulus and Setaria viridis. At an application rate of 1000 g/ha compound l.a.469 applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album, Echinocloa crus-galli and Setaria viridis.
At an application rate of 500 g/ha compound l.a.475 applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus and good herbicidal activity against Polygonum convolvulus.
At an application rate of 500 g/ha compound l.a.482 applied by the post-emergence method, showed very good herbicidal activity against Echinocloa crus-galli and good herbicidal activity against Setaria viridis. At an application rate of 500 g/ha compound l.a.487 applied by the post-emergence method, showed very good herbicidal activity against Chenopodium album.
At an application rate of 215 g/ha compound l.a.438, at an application rate of 500 g/ha compound I. a.440 and at an application rate of 1000 g/ha the compounds I. a.436 and I. a.437 applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus and Chenopodium album, and good herbicidal activity against Setaria viridis. At an application rate of 309 g/ha compound l.a.433, at an application rate of 500 g/ha the compounds l.a.9, l.a.480, l.a.481 , l.a.483, l.a.488, l.d.51 , at an application rate of 604 g/ha compound l.a.452, at an application rate of 677 g/ha compound I. a.80, at an application rate of 781 g/ha compound I. a.63, at an application rate of 958 g/ha compound I. a.77, at an application rate of 975 g/ha compound I. a.323 and at an application rate of 1000 g/ha the compounds l.a.51 , l.a.52, l.a.74, l.a.90, l.a.93, l.a.135, l.a.216, l.a.303, l.a.387, l.a.421 , l.a.425, l.a.428, l.a.435, l.a.439, l.a.448, l.a.449, l.a.460, l.a.478 and l.a.491 applied by the post-emergence method showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album and Setaria viridis. At an application rate of 272 g/ha compound l.a.49, at an application rate of 500 g/ha compound I. a.492, at an application rate of 972 g/ha compound I. a.476 and at an application rate of 1000 g/ha the compounds l.a.76, l.a.422, l.a.431 , l.a.445, l.a.454, l.a.456, l.a.457, l.a.462, l.a.465, l.a.466, l.a.470, l.a.471 , l.a.473, l.a.474, l.a.477, l.a.479, l.g.48, Lo.48 and l.r.48 applied by the post-emergence method showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album and Polygonum convolvulus.
At an application rate of 125 g/ha compound l.a.1 13 applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus and Polygonum convolvulus, and good herbicidal activity against Chenopodium album.
At an application rate of 396 g/ha compound l.a.458 applied by the post-emergence method, showed very good herbicidal activity against Amaranthus retroflexus and Chenopodium album, and good herbicidal activity against Polygonum convolvulus.
At an application rate of 250 g/ha compound Lo.51 , at an application rate of 500 g/ha compound l.w.48 and at an application rate of 1000 g/ha the compounds I. a.6, l.a.45, l.a.58, l.a.79, l.a.100, l.a.142, l.a.300, l.a.447, l.a.461 , l.a.463, l.a.464 and l.a.467 applied by the post-emergence method showed very good herbicidal activity against Amaranthus retroflexus, Chenopodium album and Echinocloa crus-galli. At an application rate of 2000 g/ha, compound l.a.489 applied by the post-emergence method, showed very good herbicidal activity against Matricaria inodora and at an application rate of 3000 g/ha very good herbicidal activity against Setaria faberi.
At an application rate of 1000 g/ha, the compounds I. a.490 applied by the post- emergence method, showed good herbicidal activity against Chenopodium album and Polygonum convolvulus.

Claims

Claims
1 . Triazines of formu
Figure imgf000083_0001
wherein
R1 is hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C2-C8-haloalkynyl, Ci-Cs-alkoxy, Ci-Cs-alkoxy-Ci-Cs- alkyl, Ci-Cs-alkylthio, Ci-Cs-alkylthio-Ci-Cs-alkyl, aminocarbonyl, (C1-C6- alkyl)aminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, C3-C6-cycloalkyl, C3-C1 cycloalkyl-Ci-Cs-alkyl, C3-C6-cycloalkyl-Ci-C8-haloalkyl, C3-C6-cycloalkyl- C2-Cs-alkenyl or C3-C6-cycloalkyl-C2-C8-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to five sub stituents selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl and C2-C6-haloalkynyl;
R2 is halogen, CN, OH, SH, Ci-Ce-alkoxy, Ci-Ce-alkylthio,
Figure imgf000083_0002
alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4-alkoxy, C1-C6- alkyltio-Ci-C4-alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxy- carbonyloxy, Ci-C6-alkylthiocarbonyloxy, aminocarbonyloxy, (C1-C6- alkyl)aminocarbonyloxy, di(Ci-C6-alkyl)aminocarbonyloxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substit uents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hy- droxycarbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6 alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino and di(Ci-C6- alkyl)amino
phenoxy or phenyl-Ci-C4-alkoxy, which phenyls are unsubstituted or substituted by one to five substit- uents selected from the group consisting of halogen, CN, NO2, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy; R3, R4 and R5 independently of one another are hydrogen, halogen, CN, NO2,
Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxy- Ci-C6-alkyl, Ci-C6-alkylsulfonyl, (Ci-C6-alkyl)amino or di(Ci-C6-alkyl)amino; including their agriculturally acceptable salts or, provided that the triazines of formula I have a carboxyl group, their agriculturally acceptable derivatives.
2. Triazines of formula I wherein
R1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2- C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl,
Ci-C6-alkylthio, Ci-C6-alkylthio-Ci-C4-alkyl, aminocarbonyl, (C1-C6- alkyl)aminocarbonyl, di(Ci-C6-alkyl)aminocarbonyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl or C3-C6-cycloalkyl-C2-C6-haloalkenyl,
which cycloalkyls are unsubstituted or substituted by one to five sub- stituents selected from the group consisting of halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl and C2-C6-haloalkynyl; R2 is halogen, CN, OH, SH, Ci-C6-alkoxy, d-Ce-alkylthio, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4-alkoxy, C1-C6- alkyltio-Ci-C4-alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxy- carbonyloxy, Ci-C6-alkylthiocarbonyloxy, aminocarbonyloxy, (C1-C6- alkyl)aminocarbonyloxy, di(Ci-C6-alkyl)aminocarbonyloxy or a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substit- uents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl,
Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hy- droxycarbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino and di(Ci-C6- alkyl)amino. The compound of formula I according to claim 1 , wherein
is Ci-Cio-alkyl, C2-Cio-alkenyl, d-Cs-haloalkyl, C2-C8-haloalkenyl, C1-C6- alkoxy-Ci-C6-alkyl, Ci-C6-alkylthio-Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6- cycloalkyl-Ci-C6-alkyl or C3-C6-cycloalkyl-Ci-C6-haloalkyl, ,
which cycloalkyls are unsubstituted or substituted by one to five sub- stituents selected from the group consisting of halogen and C1-C6- alkyl.
The compound of formula I according to claim 1 or 3, wherein
R2 is halogen, CN , OH, SH , Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci-C6- alkoxycarbonyl-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyloxy, a 5-membered heteroaryl having 2 to 4 nitrogen atoms selected from pyrazoles, imidazoles, 1 ,2,4-triazoles or tetrazoles,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 2 substit- uents selected from the group consisting of halogen, CN , NO2, C1-C6- alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl,
phenoxy or phenyl-Ci-C2-alkoxy,
which phenyls are unsubstituted or substituted by one to five substit- uents selected from the group consisting of NO2 and Ci-C2-alkoxy.
The compound of formula I according to any one of claims 1 to 4, wherein at least one of R3, R4 or R5 is hydrogen.
The compound of formula I according to any one of claims 1 to 5, wherein
R3 and R4 are independently of one another are hydrogen, halogen, CN , NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, Ci-C4-alkylsulfonyl or di(Ci-C4-alkyl)amino;
R5 is hydrogen.
The compound of formula I according to any one of claims 1 to 6, wherein R3, R4 and R5 are hydrogen.
A process for the preparation of triazines of formula I, wherein
R2 is hydroxy; and
R1 , R3, R4 and R5 are as defined in claims 1 to 7; by reaction of keto compounds of formula II
Figure imgf000086_0001
wherein R1 is as defined in claims 1 , 2 or 3; and
L1 is hydroxy, Ci-C6-alkoxy or benzyloxy, wherein the benzyl ring might be substituted by one to five nitro groups; with amidrazones of formula III
Figure imgf000086_0002
wherein R3, R4 and R5 are as defined in claims 1 , 2, 5, 6 or 7.
9. A process for the preparation of triazines of formula I wherein
R2 is Ci-C6-alkoxycarbonyloxy, Ci-C6-alkylthiocarbonyloxy, di(Ci-C6- alkyl)aminocarbonyloxy; and
R1, R3, R4 and R5 are as defined in claims 1 to 7;
by reaction of triazines of formula I, wherein R2 is hydroxy, and which are
prepared according to claim 8, with electrophiles of formula IV
R— L2
wherein
RA is Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl or di(Ci-C6- alkyl)aminocarbonyl; and
L2 is halogen, Ci-C6-alkoxy, Ci-C6-alkylcarbonyloxy, Ci-C6-alkoxy- carbonyloxy, Ci-C6-haloalkylcarbonyloxy, Ci-C6-haloalkoxycarbonyl- oxy Ci-C6-alkylsulfonyloxy, Ci-C6-haloalkylsulfonyloxy or arylsulfonyloxy.
10. A process for the preparation of triazines of formula I wherein
R2 is halogen; and
R1, R3, R4 and R5 are as defined in claims 1 to 7; by reaction of triazines of formula I, wherein R2 is hydroxy and which are
prepared according to claim 8, with a halogenating agent.
A process for the preparation of triazines of formula I wherein
R2 is CN, SH, d-Ce-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxy-Ci-C4-alkoxy, Ci C6-alkoxy-Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4-alkoxy, Ci-C6-alkyltio Ci-C4-alkylthio, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy, a 5-membered heteroaryl having 1 to 4 nitrogen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substit- uents selected from the group consisting of halogen, CN, NO2, OH, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, Ci-C6-haloalkyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hy- droxycarbonyl, thiocarboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino or di(Ci-C6- alkyl)amino
phenoxy or phenyl-Ci-C4-alkoxy,
which phenyls are unsubstituted or substituted by one to five substit- uents selected from the group consisting of halogen, CN, NO2, C1-C4 alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy ; and
R1, R3, R4 and R5 are as defined in claims 1 to 7; by reaction of triazines of formula I, wherein R2 is halogen and which are prepared according to claim 10, with nucleophiles of formula VI
R— H VI, wherein RB is CN, SH, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxy-Ci-C4- alkoxy, Ci-C6-alkoxy-Ci-C4-alkylthio, Ci-C6-alkylthio-Ci-C4- alkoxy, Ci-C6-alkyltio-Ci-C4-alkylthio, Ci-C6-alkoxycarbonyl- Ci-C6-alkoxy, or a 5-membered heteroaryl having 1 to 4 nitro- gen atoms,
which heteroaryl is attached to the triazine ring via a nitrogen atom, and which heteroaryl is unsubstituted or substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, N02, OH, d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, Ci-C6-haloalkyl, C2-C6- haloalkenyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-alkoxy- Ci-C4-alkyl, Ci-C6-alkylthio-Ci-C4-alkyl, hydroxycarbonyl, thio- carboxy, Ci-C6-alkoxycarbonyl-Ci-C4-alkyl, C1-C6- alkylthiocarbonyl-Ci-C4-alkyl, NH2, (Ci-C6-alkyl)amino or di(Ci- C6-alkyl)amino.
12. An agrochemical composition comprising a herbicidal active amount of at least one triazine of formula I as claimed in claim 1 and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substance.
13. A process for the preparation of herbicidal active agrochemical compositions, which comprises mixing a herbicidal active amount of at least one triazine of formula I as claimed in claim 1 and at least one inert liquid and/or solid carrier and, if desired, at least one surface-active substance.
14. A method of controlling undesired vegetation, which comprises allowing a
herbicidal active amount of at least one triazine of formula I as claimed in claim 1 to act on plants, their environment or on seed. 15. The use of the triazine of formula I as claimed in claim 1 as herbicides or for the desiccation/defoliation of plants.
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