WO2018234371A1 - Benzamide compounds and their use as herbicides - Google Patents

Benzamide compounds and their use as herbicides Download PDF

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Publication number
WO2018234371A1
WO2018234371A1 PCT/EP2018/066389 EP2018066389W WO2018234371A1 WO 2018234371 A1 WO2018234371 A1 WO 2018234371A1 EP 2018066389 W EP2018066389 W EP 2018066389W WO 2018234371 A1 WO2018234371 A1 WO 2018234371A1
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alkyl
group
alkoxy
haloalkyl
cycloalkyl
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PCT/EP2018/066389
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French (fr)
Inventor
Thomas Zierke
Markus Kordes
Thomas Seitz
Ryan Louis NIELSON
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to benzamide compounds and salts thereof and to compositions comprising the same.
  • the invention also relates to the use of the benzamide compounds or of the compositions comprising such compounds for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying such compounds.
  • WO 2012/028579 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)arylcarboxylic acid amides carrying 3 substituents in the 2-, 3- and 4-positions of the aryl ring and their use as herbicides.
  • WO 2013/124245 describes N-(tetrazol-5-yl)-, N-(triazol-3-yl)- and N-(1 ,3,4-oxadiazolyl)- arylcarboxylic acid amides carrying a nitro group in para position of the aryl ring, relative to the carboxamide group.
  • WO 2014/184016 relates to N-(tetrazol-5-yl)- and N-(triazol-5-yl)benzoic acid amides carrying in the meta-position of the phenyl ring, relative to the carboxamide group, an alkoxy, haloalkoxy, alkoxy-alkoxy or thio-bound group.
  • the compounds of the prior art often suffer from insufficient herbicidal activity in particular at low application rates and/or unsatisfactory selectivity resulting in a low compatibility with crop plants.
  • benzamide compounds having a strong herbicidal activity, in particular even at low application rates, a suffi- ciently low toxicity for humans and animals and/or a high compatibility with crop plants.
  • the benzamide compounds should also show a broad activity spectrum against a large number of different unwanted plants.
  • Q is Q 1 or Q 2 or Q 3 or Q 4 ,
  • Ci-Cs-alkyl-S(0) n -Z 2 is selected from the group consisting of cyano, halogen, nitro, Ci-Cs-alkyl, C2-C8- alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C 4 -alkyl, Ci-C 8 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Z 1 , Ci-C 6 -haloalkoxy, R 1 b - S(0) k -Z i ; is selected from the group consisting of Ci-C6-alkyl-S(0) n -Z 2 , Ci-C6-haloalkyl-S(0) n - Z 2 , heterocyclyl-Z 2 , where heterocyclyl is a 5- or 6-membered saturated,
  • R 5 is halogen, cyano-Z 1 , nitro, Ci-Cs-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4- alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci- Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, C1-C3- alkylcarbonyl, d-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy- Z 1 , Ci-C 4 -alkylthio-Ci-C 4 -alky
  • R 6 is selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups of the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci- C 4 -alkyl, Ci-C 4 -haloalkoxy-Ci-C 4 -alkyl, R b -S(0) n -Ci-C 3 -alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups
  • R 11 , R 21 independently of each othe are selected from the group consisting of cyano, halogen, nitro, Ci-C 6 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -halocycloalkyl, Ci-C 6 -haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci- C 4 -alkoxy-Ci-C 4 -alkoxy, C 3 -C 7 -cycloalkoxy and Ci-C 6 -haloalkoxy, or two radicals R21 bound
  • Z 1 , Z 3 independently of each other are selected from the group consisting of a covalent bond and Ci-C4-alkanediyl;
  • Z 2 is Ci-C3-alkanediyl
  • Z 3a is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, O-C1-C4- alkanediyl, Ci-C4-alkanediyl-0 and Ci-C4-alkanediyl-0-Ci-C4-alkanediyl; R b , R 1b , R 3b independently of each other are selected from the group consisting of Ci-
  • Ci- C6-haloalkyl Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl- S(0) n -Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci-
  • R 3d is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C 7 -cycloalkyl-Ci-C 4 -alkyl, where the C 3 -C 7 -cycloalkyl groups in the two
  • Ci- C6-haloalkyl Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl- S(0) n -Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci- C6-cyanoalkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group
  • R 3e , R 3f independently of each other are selected from the group consisting of hydrogen, d-Ce-alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-Ci-C 4 -alkyl, where the C 3 -C 7 - cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 - alkynyl, C3-C6-haloalkynyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of
  • Ci-C 4 -haloalkyl Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy; or
  • R3 ⁇ 4 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-
  • Ci- C6-haloalkyl C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci- C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkylsulfonyl, Ci-C 4 -alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci- C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy;
  • R 3h is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C 7 -cycloalkyl, C3- C 7 -cycloalkyl-Ci-C 4 -alkyl, where the C 3 -C 7 -cycloalkyl groups in the two
  • Ci- C6-haloalkyl C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci- C 4 -alkoxy-Ci-C 4 -alkyl, Ci-C 4 -alkylsulfonyl, Ci-C 4 -alkylcarbonyl, a radical C(0)R k , phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy; or
  • R 3 is not nitro and R 2 is Ci-C6-alkyl-S(0) n -Z 2 , Ci-C6-haloalkyl- S(0) n -Z 2 , C 3 -C 6 -cycloalkyl-S(0) n -Z 2 , heterocyclyl-Z 2a , phenyl-S(0) n -Z 2 , or heteroaryl-S(0) n -Z 2 , where the cyclic groups of the four aforementioned radicals are unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and methylsulfonyl; where Z 2a is a covalent bond or Ci-C3-alkanediyl which is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or
  • R 1 is selected from the group consisting of cyano, halogen, nitro, Ci-Cs-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci- Cs-alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkoxy-Z 1 , Ci-C 6 -haloalkoxy and R 1b -S(0) k -Z 1 ;
  • R 2 is selected from the group consisting of Ci-C 6 -alkyl-S(0) n -Z 2 , Ci-C 6 -haloalkyl-S(0) n -Z 2 , C 3 - C6-cycloalkyl-S(0) n -Z 2 , heterocyclyl-Z 2a , where heterocycly
  • R 3 is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, hydroxy- Z 3 , d-Ce-alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -Cio-cycloalkyl-Z 3 , C 3 -C 6 -cycloalkenyl-Z 3 , C3-Cio-cycloalkoxy-Z 3 , C3-Cio-cycloalkyl-Ci-C2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- cyanoalkyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, Cs-Cs-haloalkynyl, Ci-Cs-alkoxy-Z 3 , Ci-Cs- haloalkoxy-Z 3
  • heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where cyclic groups in phenyl-Z 3a and heterocyclyl-Z 3a are unsubstituted or substituted by 1 , 2, 3 or 4 groups R 21 which are identical or different; R 4 is selected from the group consisting of hydrogen, halogen, cyano-Z 1 , Ci-Cs-alkyl, nitro,
  • R 5 is halogen, cyano-Z 1 , nitro, Ci-Cs-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, C1-C3- alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs- alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z 1 , Ci-C4-alkylthio-Ci-C4- alkyl, Ci
  • R 6 is selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci- C4-alkyl, where the C3-C7-cycloalkyl groups of the two aforementioned radicals are unsub- stituted or partially or completely halogenated; Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C4-alkyl, R b -S(0) n -Ci-C3-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or
  • Z 1 , Z 3 independently of each other, are selected from the group consisting of a covalent bond and Ci-C4-alkanediyl;
  • Z 2 is Ci-C3-alkanediyl
  • Ci-C4-alkyl which is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl; is a covalent bond or Ci-C3-alkanediyl,
  • Ci-C3-alkanediyl group is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of Ci C4-alkyl and Ci-C4-haloalkyl; is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, 0-Ci-C4- alkanediyl, Ci-C4-alkanediyl-0 and Ci-C4-alkanediyl-0-Ci-C4-alkanediyl;
  • R b , R 1b , R 3b independently of each other, are selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and
  • R 3d is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C1-C6- alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S(0) n -Ci-C4-alkyl, Ci-C4-alkylamino-Ci- C4-alkyl, Ci-C4-dial
  • R3 ⁇ 4 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkylsulfonyl, Ci-C4-alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and select- ed from the group consist
  • Ci-C4-haloalkoxy; R 3h is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkylsulfonyl, Ci-C4-alkylcarbonyl, a radical C(0)R k , phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 ,
  • R 22 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Cs-Ce-cycloalkyl-Ci-Ce-alkoxy-Ci-Ce-alkyl, phenyl-Z 1 , phenyl-O-d-Ce-alkyl, phenyl-N(R 23 )- d-Ce-alkyl, phenyl-S(0) n -Ci-C
  • R 23 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl;
  • R 24 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl;
  • R 25 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci- Ce-alkoxy-d-Ce-alkyl, phenyl-Z 1 , phenyl-O-d-Ce-alkyl, phenyl-N(R 23 )-Ci-Ce-alkyl, phenyl- S(0) n -Ci-C 6 -
  • OR 23 N(R 23 ) 2 , S(0) n R 24 , S(0) 2 OR 23 , S(0) 2 N(R 23 ) 2 , and R 23 0-Ci-C 6 -alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; k is 0, 1 or 2; n is 0, 1 or 2; and
  • R k independently has the meanings of R 3c ; or a N-oxide or an agriculturally suitable salt thereof.
  • the compounds of the present invention i.e. the compounds of formula I and their agriculturally suitable salts, are particularly useful for controlling unwanted vegetation. Therefore, the invention also relates to the use of a compound of formula I or an agriculturally suitable salt thereof or of a composition comprising at least one compound of formula I or an agriculturally suitable salt thereof for combating or controlling unwanted vegetation.
  • the invention also relates to a composition comprising at least one compound of formula I, or a salt thereof, and at least one auxiliary.
  • the invention relates to an agricultural composition comprising at least one compound of formula I or an agriculturally suitable salt thereof, and at least one auxiliary customary for crop protection formulations.
  • the present invention also relates to a method for combating or controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound of formula I or a salt thereof, to act on unwanted plants, their seed and/or their habitat.
  • the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures.
  • Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group.
  • stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • the compounds of formula I may be present in the form of their tautomers.
  • the invention also relates to the tautomers of compounds of formula I and the stereoisomers and salts of said tautomers.
  • the present invention moreover relates to compounds as defined herein, wherein one or more of the atoms depicted in formula I have been replaced by its stable, preferably nonradioactive isotope (e.g., hydrogen by deuterium, 12 C by 13 C, 14 N by 15 N, 16 0 by 18 0) and in particular wherein at least one hydrogen atom has been replaced by a deuterium atom.
  • the compounds according to the invention contain more of the respective isotope than this naturally occurs and thus is anyway present in the compounds of formula I.
  • the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention in- eludes both amorphous and crystalline compounds of formula I, their enantiomers or diastere- omers, mixtures of different crystalline states of the respective compound of formula I, its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the present invention are preferably agriculturally suitable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
  • Useful agriculturally suitable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the herbicidal action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, C1-C4- hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isoprop- ylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetrame- thylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4- alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensul- fate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • weeds undesired vegetation
  • weeds is understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any).
  • Weeds, in the broadest sense, are plants considered undesirable in a particular location.
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n - Cm indicates in each case the possible number of carbon atoms in the group.
  • halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
  • partially or completely halogenated will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine.
  • a partially or completely halogenated radical is termed below also “halo-radical”.
  • partially or completely halogenated alkyl is also termed haloalkyi.
  • alkyl as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyi) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, generally from 1 to 8 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms.
  • Ci-C 4 - alkyl examples are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl (sec-butyl), isobutyl and tert-butyl.
  • Ci-C6-alkyl are, apart those mentioned for Ci-C4-alkyl, 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 and
  • Ci-Cs-alkyl are, apart those mentioned for Ci-C6-alkyl, n-heptyl, 1 -methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5- methylhexyl, 1 -ethyl pentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1 -methylheptyl, 2-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl, 1 -propylpentyl and 2-propylpentyl.
  • Ci-Cio-alkyl are, apart those mentioned for Ci-Cs-alkyl, nonyl, decyl, 2-propylheptyl and 3- propylheptyl.
  • alkylene (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is re- placed by one further binding site, thus forming a bivalent moiety.
  • Ci-C2-Alkylene or C1-C2- alkanediyl is a linear or branched divalent alkyl radical having 1 or 2 carbon atoms. Examples are -CH2-, -CH2CH2- and -CH(CH3)-.
  • Ci-C3-Alkylene or Ci-C3-alkanediyl is a linear or branched divalent alkyl radical having 1 , 2 or 3 carbon atoms.
  • Ci-C 4 -Alkylene or Ci-C 4 -alkanediyl is a linear or branched divalent alkyl radical having 1 , 2, 3 or 4 carbon atoms. Examples are -CH2-, -CH2CH2-, -CH(CH 3 )-, -CH2CH2CH2-, -CH(CH 3 )CH 2 -, -CH 2 CH(CH 3 )-, -C(CH 3 ) 2 -,
  • haloalkyi as used herein (and in the haloalkyi moieties of other groups comprising a haloalkyi group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms ("Ci-Cs-haloalkyl”), frequently from 1 to 6 carbon atoms (“C1-C6- haloalkyl”), more frequently 1 to 4 carbon atoms (“Ci-C 4 -haloalkyl”), wherein the hydrogen at- oms of this group are partially or totally replaced with halogen atoms.
  • haloalkyi as used herein (and in the haloalkyi moieties of other groups comprising a haloalkyi group, e
  • haloalkyl moieties are selected from Ci-C4-haloalkyl, more preferably from Ci-C2-haloalkyl, more preferably from halomethyl, in particular from Ci-C2-fluoroalkyl.
  • Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
  • Ci-C2-fluoroalkyl fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, pentafluoroethyl, and the like.
  • Ci-C2-haloalkyl are, apart those mentioned for Ci-C2-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chloro- fluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 2-chloroethyl, 2,2,- dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 1 -bromoethyl, and the like.
  • Ci-C4-haloalkyl are, apart those mentioned for Ci-C2-haloalkyl, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trifl uoroprop-2-yl , 3-chloropropyl, 4-chlorobutyl and the like.
  • cyanoalkyl refers to straight-chain or branched alkyl groups having 1 to 4 (“Ci-C4-cyanoalkyl”) or 1 to 6 (“Ci-C6-cyanoalkyl) carbon atoms (as mentioned above), where 1 or 2, preferably 1 , of the hydrogen atoms in these groups are replaced by a cyano (CN) group.
  • CN cyano
  • Examples are cyanomethyl, 1 -cyanoethyl, 2-cyanoethyl, 1 -cyanopropyl, 2- cyanopropyl, 3-cyanopropyl, 1 -cyanobutyl, 2-cyanobutyl, 3-cyanobutyl, 4-cyanobutyl and the like.
  • cycloalkyi as used herein (and in the cycloalkyi moieties of other groups comprising a cycloalkyi group, e.g. cycloalkoxy and cycloalkylalkyi) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms (“C3-Cio-cycloalkyl”), preferably 3 to 7 carbon atoms (“C3-C7-cycloalkyl”) or in particular 3 to 6 carbon atoms (“C3-C6- cycloalkyl").
  • Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Examples of monocyclic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.1 .1 ]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
  • cycloalkyi denotes a monocyclic saturated hydrocarbon radical.
  • halocycloalkyl as used herein (and in the halocycloalkyl moieties of other groups comprising an halocycloalkyl group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine.
  • Examples are 1 - and 2- fluorocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1 - and 2-chlorocyclopropyl, 1 ,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1 -,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1 -,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl and the like.
  • cycloalkyl-alkyl used herein denotes a cycloalkyi group, as defined above, which is bound to the remainder of the molecule via an alkylene group (or inversely expressed, it denotes an alkyl group, as described above, in which one hydrogen atom is replaced by a cycloalkyl group, as defined above).
  • C3-C7-cycloalkyl-Ci-C4-alkyl refers to a C3-C7- cycloalkyl group as defined above which is bound to the remainder of the molecule via a C1-C4- alkyl group, as defined above.
  • Examples are cyclopropylmethyl, cyclopropylethyl, cyclo- propylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentyl methyl, cyclopen- tylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, cycloheptylme- thyl, cycloheptylethyl, cycloheptylpropyl and the like.
  • C3-C6-cycloalkyl-Ci-C6-alkyl refers to a C3-C6-cycloalkyl group as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C6-alkyl group, as defined above.
  • Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentyl methyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl and the like.
  • alkenyl denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 8 (“C2-C8-alkenyl”), preferably 2 to 6 carbon atoms (“C2-C6-alkenyl”), in particular 2 to 4 carbon atoms (“C2-C4-alkenyl”), and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 - methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 - methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such as ethenyl, 1 -propenyl, 2- propenyl, 1 -methylethenyl,
  • haloalkenyl as used herein, which may also be expressed as "alkenyl which is substituted by halogen", and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 8 ("C2-C8-haloalkenyl") or 2 to 6 (“C2-C6-haloalkenyl”) or 2 to 4 (“C2-C4-haloalkenyl”) carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
  • alkynyl denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 (“C2-C8-alkynyl”), frequently 2 to 6 (“C2-C6-alkynyl”), pref- erably 2 to 4 carbon atoms (“C2-C4-alkynyl”) and a triple bond in any position, for example C2- C4-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl and the like, C2-C6-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2- butynyl, 3-butynyl, 1 -methyl-2-propynyl, 1 -pentyn
  • haloalkynyl as used herein, which is also expressed as “alkynyl which is substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 3 to 8 carbon atoms (“Cs-Cs-haloalkynyl”), frequently 3 to 6 (“C3-C6-haloalkynyl”), preferabyl 3 to 4 carbon atoms (“C3-C4-haloalkynyl”), and a triple bond in any position (as men- tioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • Cs-Cs-haloalkynyl unsaturated straight-chain or branched hydrocarbon radicals having usually 3 to 8 carbon atoms
  • C3-C6-haloalkynyl frequently 3 to 6
  • C3-C4-haloalkynyl preferabyl
  • cycloalkenyl used herein denotes a monocyclic partially unsaturated, non- aromatic hydrocarbon radical.
  • Examples for C3-C6-cycloalkenyl are cycloprop-1 -en-1 -yl, cyclo- prop-1 -en-3-yl, cyclobut-1 -en-1 -yl, cyclobut-1 -en-3-yl, cyclooct-1 -en-1 -yl, cyclopent-1 -en-1 -yl, cyclopent-1 -en-3-yl, cyclopent-1 -en-4-yl, cyclopenta-1 ,3-dien-1 -yl, cyclopenta-1 ,3-dien-2-yl, cy- clopenta-1 ,3-dien-5-yl, cyclohex-1 -en-1 -yl, cyclohex-1 -en-3-yl, cyclohex-1 -en-4-
  • alkoxy denotes in each case a straight-chain or branched alkyl group usually having from 1 to 8 carbon atoms ("d-Cs-alkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-alkoxy”), preferably 1 to 4 carbon atoms (“Ci-C4-alkoxy”), which is bound to the remainder of the molecule via an oxygen atom.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • C1-C4- Alkoxy is additionally, for example, n-propoxy, 1 -methylethoxy (isopropoxy), butoxy,
  • Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 - dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethyl butoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1 -ethyl-1
  • Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
  • haloalkoxy denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 8 carbon atoms ("Ci-Cs-haloalkoxy”), frequently from 1 to 6 carbon atoms (“Ci-C6-haloalkoxy”), preferably 1 to 4 carbon atoms (“C1-C4- haloalkoxy"), more preferably 1 to 3 carbon atoms (“Ci-C3-haloalkoxy”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms.
  • Ci-C 2 -Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHC , OCCI 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2- chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5.
  • Ci-C4-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2- bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH 2 F)-2-fluoroethoxy, 1 -(CH 2 CI)-2-chloroethoxy, 1 -(CH 2 Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
  • Ci-C6-Haloalkoxy is addi- tionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, unde- cafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluo- rohexoxy.
  • alkenyloxy denotes an alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C6-Alkenyloxy is a C2-C6-alkenyl group, as de- fined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-Cs-Alkenyloxy is a C2-C8-alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • haloalkenyloxy denotes a haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C6-Haloalkenyloxy is a C2-C6-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C8- Haloalkenyloxy is a C2-C8-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • alkynyloxy denotes an alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C6-Alkynyloxy is a C2-C6-alkynyl group, as de- fined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-Cs-Alkynyloxy is a C2-C8-alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • haloalkynyloxy denotes a haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C6-Haloalkynyloxy is a C2-C6-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • C2-C8- Haloalkynyloxy is a C2-Cs-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • Cs-Cs-Haloalkynyloxy is a Cs-Cs-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
  • alkoxyalkyl denotes in each case alkyl usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
  • alkoxy radical usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Ci-C6-alkoxy-Ci-C6-alkyl is a C1-C6- alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above.
  • Examples are CH2OCH3, CH2-OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n- butoxymethyl, (l -methylpropoxy)-methyl, (2-methylpropoxy)methyl, CH2-OC(CH3)3, 2-
  • haloalkoxy-alkyl denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above.
  • Examples are fluoromethoxymethyl, difluoro- methoxymethyl, trifluoromethoxymethyl, 1 -fluoroethoxymethyl, 2-fluoroethoxymethyl, 1 ,1 - difluoroethoxymethyl, 1 ,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl, 1 ,1 ,2- trifluoroethoxymethyl, 1 ,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethox- ymethyl, 1 -fluoroethoxy-1 -ethyl, 2-fluoroethoxy-1 -ethyl, 1 ,1 -difluoroethoxy-1 -ethyl, 1 ,2- difluoroethoxy-1 -ethyl, 2,2-difluoroethoxy-1 -ethyl, 1 ,1 ,2-trifluoroethoxy-1 -e
  • alkoxy-alkoxy refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by another alkoxy group, as defined above.
  • Ci- C4-alkoxy-Ci-C4-alkoxy refers to an alkoxy group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Examples are methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, n-butoxymethoxy, sec-butoxymethoxy, isobutoxymethoxy, tert-butoxymethoxy, 1 - methoxyethoxy, 1 -ethoxyethoxy, 1 -propoxyethoxy, 1 -isopropoxyethoxy, 1 -n-butoxyethoxy, 1 - sec-butoxyethoxy, 1 -isobutoxyethoxy, 1 -tert-butoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2- propoxyethoxy, 2-isopropoxyethoxy, 2-n-butoxyethoxy, 2-sec-butoxyethoxy, 2-isobutoxyethoxy, 2-tert-butoxyethoxy, 1 -methoxypropoxy, 1 -ethoxypropoxy, 1 -propoxypropoxy, 1 - isopropoxyprop
  • haloalkoxy-alkoxy denotes an alkoxy group, wherein one of the hydrogen atoms is replaced by an alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in one or in both alkoxy moieties) are replaced by halogen atoms.
  • Ci-C4-Haloalkoxy-Ci-C4-alkoxy is a Ci-C4-alkoxy group, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g.
  • Cycloalkoxy denotes a cycloalkyi group, as defined above, bound to the remainder of the molecule via an oxygen atom.
  • Examples of C3-C7-cycloalkoxy comprise cyclopropoxy, cy- clobutoxy, cyclopentoxy, cyclohexoxy and cycloheptoxy.
  • Examples of C3-Cio-cycloalkoxy comprise cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cy- clononoxy and cyclodecoxy.
  • cycloalkyl-alkoxy refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by a cycloalkyi group, as defined above.
  • C3- Cio-cycloalkyl-Ci-C2-alkoxy refers to an alkoxy group having 1 or 2 carbon atoms, as defined above, where one hydrogen atom is replaced by a C3-Cio-cycloalkyl group, as defined above.
  • Examples are cyclpropylmethoxy, cyclopropylethoxy, cyclobutylmethoxy, cyclo- butylethoxy, cyclopentylmethoxy, cyclopentylethoxy, cyclohexylmethoxy, cyclohexylethoxy, cy- cloheptylmethoxy, cycloheptylethoxy, cyclooctylmethoxy, cyclooctylethoxy, cyclononylmethoxy, cyclononylethoxy, cyclodecylmethoxy and cyclodecylethoxy.
  • cycloalkyl-alkoxy-alkyl refers to an alkyl group, as defined above, wherein one hydrogen atom is replaced by an alkoxy group, as defined above, where in turn in the alkoxy group one hydrogen atom is replaced by a cycloalkyi group, as defined above.
  • C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl refers to an alkyl group having 1 to 6 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci- C6-alkoxy group, as defined above, where in this alkoxy group, in turn, one hydrogen atom is replaced by a C3-C6-cycloalkyl group, as defined above.
  • alkylthio (also alkylsulfanyl, “alkyl-S” or “alkyl-S(0) k “ (wherein k is 0)) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 8 carbon atoms (“Ci-Cs-alkylthio”), frequently comprising 1 to 6 carbon atoms (“Ci-C6-alkylthio”), preferably 1 to 4 carbon atoms (“Ci-C4-alkylthio”), which is attached via a sulfur atom at any position in the alkyl group.
  • Ci-C2-Alkylthio is methylthio or ethylthio.
  • Ci-C4-Alkylthio is additionally, for example, n-propylthio, 1 -methylethylthio (iso- propylthio), butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 - dimethylethylthio (tert-butylthio).
  • Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 - methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2- dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2- dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,
  • Ci-Cs-Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
  • haloalkylthio refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine.
  • Ci-C 2 -Haloalkylthio is, for example, SCH 2 F, SCHF 2 , SCF 3 , SCH 2 CI, SCHCI 2 , SCC , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2- fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2- trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2
  • Ci-C4-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,
  • Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,
  • alkylsulfinyl and “alkyl-S(0)k” (wherein k is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • alkylsulfinyl and “alkyl-S(0)k” (wherein k is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C 2 -alkylsulfinyl refers to a Ci-C 2 -alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-alkylsulfinyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C6-alkylsulfinyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C 2 -alkylsulfinyl is methylsulfinyl or ethylsulfinyl.
  • Ci-C4-alkylsulfinyl is additionally, for example, n-propylsulfinyl,
  • C1-C6- alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2- methylbutylsulfinyl, 3-methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 -ethylpropylsulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2- methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1 ,1 -dimethylbutylsulfinyl,
  • alkylsulfonyl and “alkyl-S(0)k” (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • the term "Ci-C 2 -alkylsulfonyl” refers to a Ci-C 2 -alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C4-alkylsulfonyl refers to a Ci-C4-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C6-alkylsulfonyl refers to a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C2-alkylsulfonyl is methyl- sulfonyl or ethylsulfonyl.
  • Ci-C4-alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1 -methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1 -methylpropylsulfonyl (sec- butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert- butylsulfonyl).
  • Ci-C6-alkylsulfonyl is additionally, for example, pentylsulfonyl,
  • alkylthio-alkyl refers to a straight-chain or branched alkyl group, as defined above, where one hydrogen atom is replaced by an alkylthio group, as defined above.
  • Ci-C4-alkylthio-Ci-C4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkylthio group, as defined above.
  • Examples are methylthiomethyl, ethyl- thiomethyl, propylthiomethyl, isopropylthiomethyl, n-butylthiomethyl, sec-butylthiomethyl, isobu- tylthiomethyl, tert-butylthiomethyl, 1 -methylthioethyl, 1 -ethylthioethyl, 1 -propylthioethyl, 1 - isopropylthioethyl, 1 -n-butylthioethyl, 1 -sec-butylthioethyl, 1 -isobutylthioethyl, 1 -tert- butylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-isopropylthioethyl, 2-n- butylthioethyl, 2-sec-buty
  • alkylthio-alkylthio refers to an alkylthio group, as defined above, where one hydrogen atom is replaced by an alkylthio group, as defined above.
  • Ci-C4-alkylthio-Ci-C4-alkylthio refers to an alkylthio group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkylthio group, as defined above.
  • Examples are methylthiomethylthio, ethylthiomethylthio, propylthiomethylthio, isopropylthiomethylthio, n-butylthiomethylthio, sec-butylthiomethylthio, isobutylthiomethylthio, tert-butylthiomethylthio, 1 -methylthioethylthio, 1 -ethylthioethylthio, 1 -propylthioethylthio, 1 - isopropylthioethylthio, 1 -n-butylthioethylthio, 1 -sec-butylthioethylthio, 1 -isobutylthioethylthio, 1 - tert-butylthioethylthio, 2-methylthioethylthio, 2-ethylthioethylthio, 2-propylthioethyl
  • alkylamino denotes in each case a group R * HN-, wherein R * is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms ("C1-C6- alkylamino"), preferably 1 to 4 carbon atoms("Ci-C4-alkylamino") or 1 to 3 carbon atoms ("C1-C3- alkylamino").
  • R * is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms
  • Ci-C4-alkylamino preferably 1 to 4 carbon atoms("Ci-C4-alkylamino) or 1 to 3 carbon atoms
  • Ci-C3-alkylamino are methylamino, ethylamino, n-propylamino and isopropylamino.
  • Ci-C4-alkylamino examples include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, iso-butylamino and tert-butylamino.
  • dialkylamino denotes in each case a group R * R°N-, wherein R * and R°, independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms ("di-(Ci-C6-alkyl)-amino"), preferably 1 to 4 carbon atoms (“di- (Ci-C4-alkyl)-amino") or 1 to 3 carbon atoms (“di-(Ci-C3-alkyl)-amino").
  • Examples of a di-(Ci-C6- alkyl)-amino group are dimethylamino, diethylamino, dipropylamino, dibutylamino, methyl-ethyl- amino, methyl-propyl-amino, methyl-isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl-isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and the like.
  • alkylamino-alkyl denotes an alkyl group, as defined above, wherein one hydro- gen atom is replaced by an alkylamino group, as defined above.
  • Ci-C4-alkylamino-Ci-C4-alkyl is a Ci-C4-alkyl group, as defined above, wherein one hydrogen atom is replaced by a C1-C4- alkylamino group, as defined above. Examples are methylaminomethyl, 1 -(methylamino)-ethyl,
  • dialkylamino-alkyl denotes an alkyl group, as defined above, wherein one hydrogen atom is replaced by a dialkylamino group, as defined above.
  • Di-(Ci-C4-alkyl)-amino-Ci- C4-alkyl is a Ci-C4-alkyl group, as defined above, wherein one hydrogen atom is replaced by a di-(Ci-C4-alkyl)-amino group, as defined above.
  • Examples are dimethylaminomethyl, 1 - (dimethylamino)-ethyl, 2-(dimethylamino)-ethyl, 1 -(dimethylamino)-propyl, 2-(dimethylamino)- propyl, 3-(dimethylamino)-propyl, 1 -(dimethylamino)-butyl, 2-(dimethylamino)-butyl, 3- (dimethylamino)-butyl, 4-(dimethylamino)-butyl, (ethylmethylamino)-methyl, 1 - (ethylmethylamino)-ethyl, 2-(ethylmethylamino)-ethyl, 1 -(ethylmethylamino)-propyl, 2- (ethylmethylamino)-propyl, 3-(ethylmethylamino)-propyl, 1 -(ethylmethylamino
  • Ci-C3-alkylcarbonyl examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl and isopropylcarbonyl.
  • Examples for C1-C4- alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl n-butylcarbonyl and the like.
  • aryl refers to a mono-, bi- or tricyclic aromatic hydrocarbon rad- ical such as phenyl or naphthyl, in particular phenyl.
  • heteroaryl refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrim- idyl and the like.
  • Heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl contain one or more heteroatoms as ring members, i.e. atoms different from carbon.
  • these heteroatoms are N, O and S, where N and S can also be present as oxidized heteroatom groups, namely as NO, SO or SO2.
  • rings termed as heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl contain one or more heteroatoms and/or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2 as ring members.
  • heterocyclic rings or heterocyclyl may be saturated, partially unsaturated or maximally unsaturated.
  • Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximally unsaturated 5- or 6-membered heteromonocyclic rings are generally aromatic. Exceptions are maximally unsaturated 6-membered rings containing O, S, SO and/or SO2 as ring members, such as pyran and thiopyran, which are not aromatic. Par- tially unsaturated rings (in terms of the present invention often simply termed just as "unsaturated rings”) contain less than the maximum number of C-C and/or C-N and/or N-N double bond(s) allowed by the ring size.
  • heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • the ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
  • N can optionally be oxidized, i.e. in the form of an N-oxide, and S can also optionally be oxidized to various oxidation states, i.e. as SO or SO2.
  • An aromatic bicyclic heterocycle is an 8-, 9- or 10-membered bicyclic heterocycle consisting of a 5- or 6-membered heteroaromatic ring which is fused to a phenyl ring or to another 5- or 6-membered heteroaromatic ring.
  • the heterocycle may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
  • Examples of a 3-, 4-, 5- or 6-membered monocyclic saturated heterocycle include:
  • oxirane-2-yl aziridine-1 -yl, aziridine-2-yl, oxetan-2-yl, azetidine-1 -yl, azetidine-2-yl, azetidine-3- yl, thietane-1 -yl, thietan-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahy- drothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1 -yl, imidazolidin-2-yl, imidazo
  • Examples of a 5- or 6-membered monocyclic partially unsaturated heterocycle include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin- 3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2- isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxa
  • a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring is e.g. a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring.
  • Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3- pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,
  • Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include benzofuranyl, benzothienyl, indolyl, indazolyl, ben- zimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, iso- chinolinyl, purinyl, 1 ,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.
  • Heterocyclyl in heterocyclyl-Z 2a in the definition of R 2 is a 5- or 6-membered saturated, S(0) n -containing heterocycle. Generally, it contains 1 or 2 S(0) n groups as ring member(s). Examples therefor are tetrahydrothien-2-yl, tetrahydrothien-3-yl, 1 -oxo-tetrahydrothien-2-yl, 1 -oxo- tetrahydrothien-3-yl, 1 ,1 -dioxotetrahydrothien-2-yl, 1 ,1 -dioxotetrahydrothien-3-yl, tetrahydrothi- opyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1 -oxo-tetrahydrothiopyran-2-yl, 1 -oxo-te
  • Preferred compounds according to the invention are compounds of formula I or a stereoisomer, or salt thereof, wherein the salt is an agriculturally suitable salt.
  • Particularly preferred compounds according to the invention are compounds of formula I or a salt thereof, especially an agriculturally suitable salt thereof.
  • variable Q in the compounds of formula I is Q 2 :
  • variable Q in the compounds of formula I is Q 3 :
  • variable Q in the compounds of formula I is Q 4 :
  • Q is Q 1 .
  • Preferred compounds according to the invention are compounds of formula I, wherein R 1 is selected from the group consisting of cyano, halogen, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy- Z 1 , R 1b -S(0)k-Z 1 , where k and Z 1 are as defined herein and where R 1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl.
  • Z 1 is in particular a covalent bond.
  • R 1 is selected from halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z 1 and R 1b -S(0)k-Z 1 , where k and Z 1 are as defined herein and where R 1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl.
  • Z 1 is in particular a covalent bond.
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl. More particularly, R 1 is F, CI, Br, I, nitro, CH 3 , SCH 3 , SCF 3 , SO2CH3 or CH2OCH2CH2OCH3, and specifically R 1 is F, CI, Br, I, nitro, CH3, SCH3 or SO2CH3. More specifically, R 1 is halogen (i.e. F, CI, Br or I), even more specifically CI or Br, and very specifically CI.
  • R 1 is halogen (i.e. F, CI, Br or I), even more specifically CI or Br, and very specifically CI.
  • the radicals Ci-C 6 -alkyl-S(0) n -Z 2 , Ci-C 6 -haloalkyl-S(0) n -Z 2 , C 3 -C 6 - cycloalkyl-S(0)n-Z 2 , heterocyclyl-Z 2a , phenyl-S(0) n -Z 2 and heteroaryl-S(0) n -Z 2 are bound via the bridging group Z 2 or Z 2a to the remainder of the molecule; i.e. to the oxygen atom.
  • Preferred compounds according to the invention are compounds of formula I , wherein R 2 is Ci- C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, preferably from the group consisting of halogen and Ci-C4-haloalkyl; and specifically from halogen.
  • R 2 is Ci-C3-alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 , wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, preferably from the group consisting of halogen and Ci-C4-haloalkyl; and specifically from halogen.
  • R 2 is H3C-S(0) n -Z 2 or phenyl-S(0) n -Z 2 , wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen.
  • R 2 is H3C-S(0) n -Z 2 or phenyl-S(0) n -Z 2 , wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from F and CI.
  • R 2 is phenyl-S(0) n -Z 2 , wherein the phenyl ring is substituted by Ci-C4-haloalkyl, preferably by Ci-C2-haloalkyl, specifically by CF3.
  • Z 2 is Ci-C3-alkanediyl
  • Z 2 is Ci-C2-alkanediyl, which is unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of C
  • Ci-C2-alkanediyl which is unsubstituted
  • d-alkanediyl which is unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of C
  • R 2 even more preferably however unsubstituted d-alkanediyl; specifically CH2CH2.
  • the index n is in particular 0.
  • R 2 is more preferably d-d-alkyl-S-Z 2 or phenyl-S(0) n -Z 2 with n being 0, 1 or 2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group con- sisting of halogen, d-d-alkyl, d-d-haloalkyl and d-d-alkoxy, preferably from the group consisting of halogen and d-d-haloalkyl; and specifically from halogen; where Z 2 has one the above general or, in particular, one of the above preferred meanings.
  • R 2 is d-d-alkyl-S-Z 2 or phenyl-S(0) n -Z 2 with n being 0, 1 or 2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, d-d-alkyl, d-d-haloalkyl and d-d-alkoxy, preferably from the group consisting of halogen and d-d-haloalkyl; and specifically from halogen; where Z 2 has one the above general or, in particular, one of the above preferred meanings.
  • R 2 is Ci-d-alkyl-S-CH 2 CH 2 or phenyl-S(0)n-CH 2 CH2 with n being 0, 1 or 2, where- in the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group consisting of halogen, d-d-alkyl, d-d-haloalkyl and d-d-alkoxy, preferably from the group consisting of halogen and d-d-haloalkyl; and specifically from halogen, and is more particularly d-d-alkyl-S-ChbChb or phenyl-S(0) n -CH2CH2 with n being 0, 1 or 2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group consisting of halo- gen, d-d-alkyl, d-d-haloalkyl and d-d-alkoxy, preferably
  • R 2 is C3-C6-cycloalkyl-S(0) n -Z 2 , more preferably C3- C6-cycloalkyl-S-Z 2 , in particular Cs-Ce-cycloalkyl-S-ChbCI-b and specifically cyclopropyl-S-
  • R 2 is heterocyclyl-Z 2a , where heterocyclyl is a 5- or 6- membered saturated heterocycle which contains one S(0) n group as ring member, where Z 2a has one of the above general or, in particular, one of the below preferred meanings. More preferably, R 2 is heterocyclyl-Z 2a , where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S atom as ring member; where Z 2a has one of the above general or, in particular, one of the below preferred meanings.
  • Z 2a is preferably a bond or unsubstitueted Ci-C2-alkanediyl, in particular a bond or Chb; and is specifically a bond.
  • R 2 is heterocyclyl-Z 2a , where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S(0) n group as ring member, where Z 2a is a bond or unsubstitueted Ci-C2-alkanediyl, in particular a bond or Chb; and is specifically a bond. More particularly, R 2 is heterocyclyl-Z 2a , where heterocyclyl is a 5- or 6- membered saturated heterocycle which contains one S atom as ring member; where Z 2a is a bond or unsubstitueted Ci-C2-alkanediyl, in particular a bond or Chb; and is specifically a bond. Specifically, R 2 is heterocyclyl-Z 2a , where heterocyclyl is a 6-membered saturated heterocycle which contains one S atom as ring member; where Z 2a is a bond or CH2; and is specifically a bond.
  • Preferred compounds according to the invention are compounds of formula I, wherein R 3 is selected from the group consisting of hydrogen, cyano, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-alkenyloxy, C2-C4- alkynyloxy or R 3b -S(0)k, where the variables k and R 3b have one of the herein defined mean- ings; in particular, R 3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, or R 3b -S(0)k, where the variables k and R 3b have one of the herein defined meanings.
  • R 3 is selected from the group consisting of hydrogen, halogen, C1-C4- alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkyl-S(0), Ci-C 4 -haloalkyl-S(0), Ci-C 4 -alkyl-S(0) 2 , and Ci-C 4 -haloalkyl-S(0) 2 .
  • R 3 is selected from the group consisting of halogen, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl and more particularly from halogen and Ci-C4-alkylsulfonyl.
  • R 3 is selected from the group consisting of from halogen (i.e. CI, F, Br, I) and S(0)2CH3, and more specifically from halogen; even more specifically from CI, Br and I, and very specifically from CI and Br.
  • R 3c is preferably selected from the group consisting of Ci-C6-alkyl, C3- C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-Ci-C4-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, phenyl, and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy;
  • R 3c is selected from the group consisting of CrC 4 -alkyl, C 3 -C 7 -cycloalkyl, d- C 4 -haloalkyl, CrC 4 -alkoxy, and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 groups, which are identical or different and selected from the group consisting of halogen and CrC 4 -alkoxy;
  • R 3c is methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr),
  • R 3d is preferably selected from the group consisting of Ci-C6-alkyl, C3- C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C 4 -alkyl, Ci-C6-haloalkyl and phenyl where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy; more preferably, R 3d is selected from the group consisting of Ci-C 4 -alkyl, C3-C7-cycloalkyl, and Ci-C 4 -haloalkyl;
  • R 3d is methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr),
  • Preferred compounds according to the invention are compounds of formula I, wherein in R 3 , Z 3 is Ci-C 4 -alkanediyl; preferably, Z 3 is -CH2- or -CH2CH2-.
  • Z 3 is a covalent bond.
  • Preferred compounds according to the invention are compounds of formula I, wherein R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl, and C1-C2- haloalkyl.
  • R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, CH3, CHF2, and CF3, in particular from hydrogen, cyano, chlorine, fluorine and CH3.
  • R 4 is hydrogen, chlorine or fluorine.
  • Most preferred compounds according to the invention are compounds of formula I, wherein R 4 is hydrogen.
  • Preferred compounds according to the invention are compounds of formula I, wherein R 5 is selected from the group consisting of CHF2, CF3 and halogen.
  • R 5 is halogen, in particular chlorine or fluorine, specifically fluorine.
  • Preferred compounds according to the invention are compounds of formula I, wherein R 6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl.
  • R 6 is selected from the group consisting of Ci-C2-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, specifically from CH 3 , CH3CH2, CH3OCH2CH2 and CH3OCH2.
  • R 6 is C1-C4- alkyl, more specifically Ci-C2-alkyl, and very specifically methyl.
  • R 11 is selected from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkoxy-Ci- C4-alkoxy and Ci-C6-haloalkyloxy, more preferably from halogen, Ci-C4-alkyl,
  • R 11 is selected from the group consisting of halogen, Ci-C4-alkyl, C3-C6- cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy; in particular from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy; and specifically from CI, F, Br, methyl, ethyl, methoxy and trifluoromethyl.
  • R 21 is selected from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkoxy-Ci- C4-alkoxy and Ci-C6-haloalkyloxy, more preferably from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy.
  • R 21 is selected from the group consisting of halogen, Ci-C4-alkyl, C3-C6- cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy; in particular from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy; and specifically from CI, F, Br, methyl, ethyl, methoxy and trifluoromethyl.
  • Z 1 , Z 3 independently of each other are selected from a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond.
  • Z 3a is selected from a covalent bond, Ci-C2-alkanediyl, 0-Ci-C2-alkanediyl, C1-C2- alkanediyl-0 and Ci-C2-alkanediyl-0-Ci-C2-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyI, O-ethanediyI, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.
  • R b , R 1b , R 3b independently of each other are selected from Ci-C6-alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy.
  • R b , R 1b , R 3b independently of each other are selected from the group consisting of Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.
  • R b , R 1b , R 3b independently of each other are selected from Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
  • R 3c , R k independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of
  • R 3c , R k independently of each other are selected from hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.
  • R 3c , R k independently of each other are selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
  • R 3d is selected from Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl.
  • R 3d is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C3-C6-cycloalkyl.
  • R 3e , R 3f independently of each other are selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci- C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4- haloalkyl and Ci-C4-alkoxy, or R 3e and R 3f together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a
  • R 3e , R 3f independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl and benzyl, or R 3e and R 3f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
  • R 3e , R 3f independently of each other are selected from hydrogen and C1-C4- alkyl, or R 3e and R 3f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups.
  • R3 ⁇ 4 is selected from hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl.
  • R3 ⁇ 4 is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci- C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl.
  • R 3h is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci- C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl; or
  • R 3 9 and R 3h together with the nitrogen atom, to which they are bound may form a 5-, 6 or
  • R3 ⁇ 4 and R 3h together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl;
  • R3 ⁇ 4 and R 3h together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups.
  • n and k independently of each other are 0 or 2, and in particular 2.
  • n is 0.
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z 1 and R 1b -S(0)k-Z 1 , where k and Z 1 are as defined herein and where R 1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl.
  • Z 1 is in particular a covalent bond.
  • R 1 is selected from F, CI, Br, I, nitro, CH 3 , SCHs, SCFs, SO2CH3, and CH2OCH2CH2OCH3; and
  • R 3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkyl-S(0), C1-C4- haloalkyl-S(O), Ci-C 4 -alkyl-S(0) 2 , and Ci-C 4 -haloalkyl-S(0) 2 .
  • R 3 is selected from CI, F, Br, I, CH 3 , CF 3 , CHF 2 , OCF 3 , OCHF 2 , SCH 3 , SCF 3 , SCHF 2 , S(0)CH 3 , S(0)CH 2 CH 3 , S(0) 2 CH 3 and S(0) 2 CH 2 CH 3 .
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl, in particular from F, CI, Br, I, nitro, CH 3 , SCH 3 and SO2CH3; and R 3 is selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2- haloalkoxy, Ci-C 2 -alkylthio, Ci-C 2 -haloalkylthio, Ci-C 2 -alkyl-S(0), Ci-C 2 -haloalkyl-S(0), C1-C2- alkyl-S(0) 2 and Ci-C 2 -haloalkyl-S(0) 2 , most particular from
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z 1 and R 1b -S(0)k-Z 1 , where k and Z 1 are as defined herein and where R 1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl.
  • Z 1 is in particular a covalent bond; specifically R 1 is selected from F, CI, Br, I, nitro, CH 3 , SCH 3 , SCF 3 , S0 2 CH 3 , and CH 2 OCH 2 CH 2 OCH 3 ;
  • R 2 is Ci-C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
  • Z 2 is Ci-C 2 -alkanediyl, which is unsubstitueted;
  • n 0;
  • R 3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkyl-S(0), C1-C4- haloalkyl-S(0),Ci-C 4 -alkyl-S(0) 2 , and Ci-C 4 -haloalkyl-S(0) 2 , in particular from CI, F, Br, I, CH 3 , CF 3 , CHF 2 , OCF 3 , OCHF 2 , SCH 3 , SCF 3 , SCHF 2 , S(0)CH 3 , S(0)CH 2 CH 3 , S(0) 2 CH 3 and
  • R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C 2 -alkyl, and Ci-C 2 -haloalkyl;
  • R 5 is selected from the group consisting of halogen, CHF 2 and CF 3 ;
  • R 6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH 3 , CH 3 CH 2 , CH 3 OCH 2 CH 2 and CH 3 OCH 2 .
  • Q is Q 1 , Q 2 , Q 3 or Q 4 and the variables R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the following meanings:
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z 1 and R 1b -S(0)k-Z 1 , where k and Z 1 are as defined herein and where R 1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl.
  • Z 1 is in particular a covalent bond; specifically R 1 is selected from F, CI, Br, I, nitro, CH 3 , SCH 3 , SCF 3 , S0 2 CH 3 , and CH 2 OCH 2 CH 2 OCH 3 ;
  • R 2 is Ci-C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
  • Z 2 is Ci-C 2 -alkanediyl, which is unsubstitueted;
  • R 3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C 4 -alkyl-S(0), C1-C4- haloalkyl-S(0), Ci-C 4 -alkyl-S(0) 2 , and Ci-C 4 -haloalkyl-S(0) 2 , in particular from CI, F, Br, I, CH 3 , CF 3 , CHF 2 , OCF3, OCHF2, SCHs, SCFs, SCHF 2 , S(0)CH 3 , S(0)CH 2 CH 3 , S(0) 2 CH 3 and
  • R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C 2 -alkyl, and Ci-C 2 -haloalkyl;
  • R 5 is selected from the group consisting of halogen, CHF 2 and CF 3 ;
  • R 6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phe- nyl, in particular from CH 3 , CH 3 CH 2 , CH 3 OCH 2 CH 2 and CH 3 OCH 2 .
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl; specifically R 1 is F, CI, Br, I , nitro, CH 3 , SCH 3 or S0 2 CH 3 ;
  • R 2 is Ci-C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
  • Z 2 is Ci-C 2 -alkanediyl, which is unsubstitueted;
  • n 0;
  • R 3 is selected from the group consisting of halogen, Ci-C 2 -alkyl, Ci-C 2 -haloalkyl, Ci-C 2 - haloalkoxy, Ci-C 2 -alkylthio, Ci-C 2 -haloalkylthio, Ci-C 2 -alkyl-S(0), Ci-C 2 -haloalkyl-S(0), Ci-C 2 - alkyl-S(0) 2 and Ci-C 2 -haloalkyl-S(0) 2 , and more specifically from CI, Br, I, CF 3 , SCH 3 , S(0)CH 3 and S(0) 2 CH 3 ;
  • R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, CH 3 , CHF 2 , and CF 3 ;
  • R 5 is selected from the group consisting of halogen
  • R 6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH 3 , CH 3 CH 2 , CH 3 OCH 2 CH 2 and CH 3 OCH 2 .
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl; specifically R 1 is F, CI, Br, I , nitro, CH 3 , SCH 3 or S0 2 CH 3 ;
  • R 2 is Ci-C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
  • Z 2 is Ci-C 2 -alkanediyl, which is unsubstitueted;
  • R 3 is selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2- haloalkoxy, Ci-C 2 -alkylthio, Ci-C 2 -haloalkylthio, Ci-C 2 -alkyl-S(0), Ci-C 2 -haloalkyl-S(0), C1-C2- alkyl-S(0) 2 and Ci-C 2 -haloalkyl-S(0) 2 , and more specifically from CI, Br, I, CF 3 , SCH 3 , S(0)CH 3 and S(0) 2 CH 3 ;
  • R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, CH 3 , CHF2, and CF 3 ;
  • R 5 is selected from the group consisting of F
  • R 6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH 3 , CH 3 CH 2 , CH 3 OCH 2 CH 2 and CH 3 OCH 2 .
  • R 1 is F, CI, Br, I, nitro, CH 3 , SCH 3 , SCF 3 , S0 2 CH 3 , and CH 2 OCH 2 CH 2 OCH 3 ;
  • R 2 is Ci-C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
  • Z 2 is Ci-C2-alkanediyl, which is unsubstitueted
  • n 0;
  • R 3 is selected from the group consisting of CI, F, Br, I, CH 3 , CF 3 , CHF2, OCF 3 , OCHF2, SCH 3 , SCF 3 , SCHF 2 , S(0)CH 3 , S(0)CH 2 CH 3 , S(0) 2 CH 3 and S(0) 2 CH 2 CH 3 ;
  • R 4 is hydrogenCI or F
  • R 5 is selected from the group consisting of chlorine and fluorine
  • R 6 is selected from the group consisting of CH 3 , CH 3 CH 2 , CH 3 OCH 2 CH 2 and CH 3 OCH 2 .
  • Q is Q 1 , Q 2 , Q 3 or Q 4 and the variables R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the following meanings:
  • R 1 is F, CI, Br, I, nitro, CH 3 , SCH 3 , SCF 3 , S0 2 CH 3 , and CH 2 OCH 2 CH 2 OCH 3 ;
  • R 2 is Ci-C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
  • Z 2 is Ci-C2-alkanediyl, which is unsubstitueted
  • n 0;
  • R 3 is selected from the group consisting of CI, F, Br, I, CH 3 , CF 3 , CHF2, OCF 3 , OCHF2, SCH 3 , SCF 3 , SCHF 2 , S(0)CH 3 , S(0)CH 2 CH 3 , S(0) 2 CH 3 and S(0) 2 CH 2 CH 3 ;
  • R 4 is hydrogen, chlorine or fluorine
  • R 5 is selected from the group consisting of halogen, CHF2 and CF 3 ;
  • R 6 is selected from the group consisting of CH 3 , CH 3 CH 2 , CH 3 OCH 2 CH 2 and CH 3 OCH 2 .
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z 1 and R 1b -S(0)k-Z 1 , where k and Z 1 are as defined herein and where R 1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl.
  • Z 1 is in particular a covalent bond; specifically R 1 is selected from F, CI, Br, I, nitro, CH 3 , SCH 3 , SCF 3 , SO2CH3, and
  • R 2 is Ci-C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
  • Z 2 is Ci-C2-alkanediyl, which is unsubstitueted
  • n 0;
  • R 3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, Ci-C -alkyl-S(0), Ci-C 4 -haloalkyl-S(0), Ci-C 4 -alkyl-S(0)2, and Ci-C 4 -haloalkyl-S(0) 2 , in particular from CI, F, Br, I, CH 3 , CF 3 , CHF 2 , OCF 3 , OCHF 2 , SCH 3 , SCF 3 , SCHF 2 , S(0)CH 3 , S(0)CH 2 CH 3 , S(0) 2 CH 3 and S(0) 2 CH 2 CH 3 ;
  • R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl, and Ci-C2-haloalkyl;
  • R 5 is selected from the group consisting of chlorine and fluorine
  • R 6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH 3 , CH 3 CH 2 , CH 3 OCH 2 CH 2 and CH 3 OCH 2 .
  • R 1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl; spe- cifically R 1 is F, CI, Br, I, nitro, CH 3 , SCH 3 or S0 2 CH 3 ;
  • R 2 is Ci-C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
  • Z 2 is Ci-C2-alkanediyl, which is unsubstitueted
  • n 0
  • R 3 is selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2- haloalkoxy, Ci-C 2 -alkylthio, Ci-C 2 -haloalkylthio, Ci-C 2 -alkyl-S(0), Ci-C 2 -haloalkyl- S(O), Ci-C 2 -alkyl-S(0) 2 and Ci-C 2 -haloalkyl-S(0) 2 , and more specifically from CI, Br, I, CF 3 , SCH 3 , S(0)CH 3 and S(0) 2 CH 3 ;
  • R 4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, CH 3 , CHF2, and CF 3 ;
  • R 5 is selected from the group consisting of chlorine and fluorine
  • R 6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH 3 , CH 3 CH 2 , CH 3 OCH 2 CH 2 and CH 3 OCH 2 .
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the following meanings:
  • R 1 is F, CI, Br, I, nitro, CH 3 , SCH 3 , SCF 3 , SO2CH3, and CH2OCH2CH2OCH3;
  • R 2 is Ci-C 6 -alkyl-S(0) n -Z 2 or phenyl-S(0) n -Z 2 ,
  • phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
  • Z 2 is Ci-C2-alkanediyl, which is unsubstitueted
  • n 0;
  • R 3 is selected from the group consisting of CI, F, Br, I , CH3, CF3, CHF2, OCF3, OCHF2,
  • R 4 is hydrogen, chlorine or fluorine
  • R 5 is selected from the group consisting of chlorine and fluorine
  • R 6 is selected from the group consisting of CH 3 , CH3CH2, CH3OCH2CH2 and CH3OCH2.
  • Q is Q 1 ;
  • R 1 is halogen
  • R 2 is Ci-C6-alkyl-S(0) n -Z 2 ; phenyl-S(0) n -Z 2 , wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy; C3-C6-cycloalkyl-S(0) n -Z 2 ; or heterocyclyl-Z 2a , where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S(0) n group as ring member, where Z 2 , Z 2a and n have one of the above general or, in particular one of the above preferred meanings;
  • R 3 is selected from the group consisting of halogen, Ci-C4-alkylsulfonyl and C1-C4- haloalkylsulfonyl;
  • R 4 is hydrogen
  • R 5 is halogen
  • R 6 is Ci-C 4 -alkyl.
  • Q is Q 1 ;
  • R 1 is halogen
  • R 2 is Ci-C6-alkyl-S-Z 2 ; phenyl-S(0) n -Z 2 , wherein n is 0, 1 or 2 and wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy; C3-C6-cycloalkyl-S-Z 2 ; or hetero- cyclyl-Z 2a , where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S atom as ring member, where Z 2 is unsubstituted Ci-C2-alkanediyl and Z 2a is a bond or unsubstitueted Ci-C2-alkanediyl;
  • R 3 is selected from the group consisting of halogen and Ci-C4-alkylsulfonyl;
  • R 4 is hydrogen
  • R 5 is halogen
  • R 6 is Ci-C 4 -alkyl.
  • Q is Q 1 ;
  • R 1 is halogen
  • R 2 is C-i-Cs-alkyl-S-ChbCI-b; phenyl-S(0)n-CH 2 CH2, wherein n is 0, 1 or 2 and wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy; C3-C6-cycloalkyl-S-
  • heterocyclyl-Z 2a where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S atom as ring member, where Z 2a is a bond or Chb;
  • R 3 is selected from the group consisting of halogen and Ci-C4-alkylsulfonyl;
  • R 4 is hydrogen
  • R 5 is halogen
  • R 6 is Ci-C 4 -alkyl.
  • Q is Q 1 ;
  • R 1 is halogen
  • R 2 is Ci-C 3 -alkyl-S-CH2CH 2 ; phenyl-S(0)n-CH 2 CH2, wherein n is 0, 1 or 2 and wherein the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy; cyclopropyl-S-Z 2 or heterocyclyl-Z 2a , where heterocyclyl is a 6-membered saturated heterocycle which con- tains one S atom as ring member, where Z 2a is a bond or Chb;
  • R 3 is selected from the group consisting of halogen and Ci-C2-alkylsulfonyl
  • R 4 is hydrogen
  • R 5 is halogen
  • R 6 is Ci-C 2 -alkyl.
  • Q is Q 1 ;
  • R 1 is CI or Br; in particular CI;
  • R 2 is Ci-C 3 -alkyl-S-CH2CH 2 ; phenyl-S(0) n -CH 2 CH 2 , wherein n is 0, 1 or 2 and wherein the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy, in particular from halogen and Ci-C2-haloalkyl; cyclopropyl-S-ChbCI-b or heterocyclyl-Z 2a , where heterocyclyl is a 6-membered saturated heterocycle which contains one S atom as ring member, where Z 2a is a bond or Chb, in particular a bond;
  • R 3 is selected from the group consisting of CI, Br and methylsulfonyl
  • R 4 is hydrogen
  • R 5 is CI or F
  • R 6 is Ci-C 2 -alkyl.
  • Q is Q 1 ;
  • R 1 is CI or Br; in particular CI;
  • R 3 is selected from the group consisting of CI and Br;
  • R 4 is hydrogen
  • R 5 is F
  • R 6 is Ci-C 2 -alkyl.
  • Table 1 Compounds of formula I.A.I (I.A.I.1 - I.A 1.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 2 Compounds of formula I.A.II (I.A.II.1 - I.A.II.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 5 Compounds of formula I.A.V (I.A.V.1 - I.A.V.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 7 Compounds of formula I.B.I (I.B.1.1 - 1. B.I.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 8 Compounds of formula I.B.II (I. B.11.1 - I.B.II.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 1 Compounds of formula I.B.V (I.B.V.1 - I.B.V.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 12 Compounds of formula I.B.VI (I.B.VI.1 - I.B.VI.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 13 Compounds of formula I.C.I (I.C.I.1 - 1. C.I.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 14 Compounds of formula I.C.II (I.C.II.1 - 1. CM.1332) in which the combination of R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 15 Compounds of formula I.C.III (I.C.III.1 - I.C.III.1332) in which the combination of R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 17 Compounds of formula I.C.V (I.C.V.1 - I.C.V.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 18 Compounds of formula I.C.VI (I.C.VI.1 - I.C.VI.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 20 Compounds of formula I.D.II (I. D.11.1 - I.D.II.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 21 Compounds of formula I.D.III (I.D.III.1 - 1. D. III.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 22 Compounds of formula I.D.IV (I.D.IV.1 - I.D.IV.1332) in which the combination of R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;
  • Table 23 Compounds of formula I.D.V (I.D.V.1 - I.D.V.1332) in which the combination of R 1 , R 2 , R 3 and R 5 for a compound corresponds in each case to one row of Table A;

Abstract

The invention relates to benzamides of formula (I), wherein Q is Q1 or Q2 or Q3 or Q4, and the other variables are as defined in the claims and the description. The invention further relates to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.

Description

Benzamide compounds and their use as herbicides
Description
The present invention relates to benzamide compounds and salts thereof and to compositions comprising the same. The invention also relates to the use of the benzamide compounds or of the compositions comprising such compounds for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying such compounds.
For the purposes of controlling unwanted vegetation, especially in crops, there is an ongoing need for new herbicides which have high activities and selectivities together with a substantial lack of toxicity for humans and animals.
WO 2012/028579 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)arylcarboxylic acid amides carrying 3 substituents in the 2-, 3- and 4-positions of the aryl ring and their use as herbicides. WO 2013/124245 describes N-(tetrazol-5-yl)-, N-(triazol-3-yl)- and N-(1 ,3,4-oxadiazolyl)- arylcarboxylic acid amides carrying a nitro group in para position of the aryl ring, relative to the carboxamide group. WO 2014/184016 relates to N-(tetrazol-5-yl)- and N-(triazol-5-yl)benzoic acid amides carrying in the meta-position of the phenyl ring, relative to the carboxamide group, an alkoxy, haloalkoxy, alkoxy-alkoxy or thio-bound group. The compounds of the prior art often suffer from insufficient herbicidal activity in particular at low application rates and/or unsatisfactory selectivity resulting in a low compatibility with crop plants.
Accordingly, it is an object of the present invention to provide further benzamide compounds having a strong herbicidal activity, in particular even at low application rates, a suffi- ciently low toxicity for humans and animals and/or a high compatibility with crop plants. The benzamide compounds should also show a broad activity spectrum against a large number of different unwanted plants.
These and further objectives are achieved by the compounds of formula I defined below and their agriculturally suitable salts.
Therefore, in a first aspect the present invention relates to compounds of formula I,
Figure imgf000002_0001
Q is Q1 or Q2 or Q3 or Q4,
Figure imgf000003_0001
is selected from the group consisting of cyano, halogen, nitro, Ci-Cs-alkyl, C2-C8- alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C4-alkyl, Ci-C8-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1 , Ci-C6-haloalkoxy, R1 b- S(0)k-Zi ; is selected from the group consisting of Ci-C6-alkyl-S(0)n-Z2, Ci-C6-haloalkyl-S(0)n- Z2, heterocyclyl-Z2, where heterocyclyl is a 5- or 6-membered saturated, S(0)n containing heterocycle, phenyl-S(0)n-Z2, heteroaryl-S(0)n-Z2, where the cyclic groups of the three aforementioned radicals are unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and methylsulfonyl; is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, nitro, hydroxy-Z3, Ci-C6-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, C3-Cio-cycloalkyl-Z3, C3- C6-cycloalkenyl-Z3, C3-Cio-cycloalkoxy-Z3, C3-Cio-cycloalkyl-Ci-C2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C4-cyanoalkyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C3- Cs-haloalkynyl, Ci-Cs-alkoxy-Z3, Ci-Cs-haloalkoxy-Z3, Ci-C4-alkoxy-Ci-C4-alkoxy-Z3, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z3, C2-C8-alkenyloxy-Z3, C2-C8-alkynyloxy-Z3, C2-C8- haloalkenyloxy-Z3, C3-C8-haloalkynyloxy-Z3, R3b-S(0)k-Z3, R3c-C(0)-Z3, R3dO-C(0)- Z3, R3dO-N=CH-Z3, R3eR3fN-C(0)-Z3, R¾R3hN-Z3, R22C(0)0-Z3, R25OC(0)0-Z3, (R22)2NC(0)0-Z3, R25S(0)20-Z3, R22OS(0)2-Z3, (R22)2NS(0)2-Z3, R25OC(0)N(R22)-Z3, (R22)2NC(0)N(R22)-Z3, (R22)2NS(0)2N(R22)-Z3, (OH)2P(0)-Z3, (Ci-C4-alkoxy)2P(0)-Z3, phenyl-Z3a, heterocyclyl-Z3a, where heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where cyclic groups in phenyl-Z3a and heterocyclyl-Z3a are unsubstituted or substituted by 1 , 2, 3 or 4 groups R21 , which are identical or different; is selected from the group consisting of hydrogen, halogen, cyano-Z1 , Ci-Cs-alkyl, , nitro, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, C1-C3- dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C4-alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C C6-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z1, R1 b-S(0)k-Z1 , phenoxy-Z1 and heterocyclyloxy-Z1, where heterocydyloxy is an oxygen bound 5- or 6- membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocy- clyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11, which are identical or different;
R5 is halogen, cyano-Z1, nitro, Ci-Cs-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4- alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci- Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, C1-C3- alkylcarbonyl, d-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy- Z1, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C4-alkoxy-Z1, R1b-S(0)k-Z1, phenoxy-Z1 and heterocyclyloxy-Z1, where heterocy- clyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11, which are identical or different;
R6 is selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups of the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci- C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Rb-S(0)n-Ci-C3-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C C4-alkyl, CrC4-haloalkyl, C C4-alkoxy and C C4-haloalkoxy;
R11, R21 independently of each othe are selected from the group consisting of cyano, halogen, nitro, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci- C4-alkoxy-Ci-C4-alkoxy, C3-C7-cycloalkoxy and Ci-C6-haloalkoxy, or two radicals R21 bound to the same carbon atom together may form a group =0;
Z1, Z3 independently of each other are selected from the group consisting of a covalent bond and Ci-C4-alkanediyl;
Z2 is Ci-C3-alkanediyl,
which is unsubstituted or substituted by 1 , 2, 3 or 4 groups,
which are identical or different and selected from the group consisting of C1-C4- alkyl and CrC4-haloalkyl; Z3a is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, O-C1-C4- alkanediyl, Ci-C4-alkanediyl-0 and Ci-C4-alkanediyl-0-Ci-C4-alkanediyl; Rb, R1b, R3b independently of each other are selected from the group consisting of Ci-
C6-alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C3-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; R3c is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-
C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two
aforementioned radicals are unsubstituted or partially or completely halogenated, Ci- C6-haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl- S(0)n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci-
C6-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkoxy and Ci-C4-haloalkoxy;
R3d is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two
aforementioned radicals are unsubstituted or partially or completely halogenated, Ci- C6-haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl- S(0)n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci- C6-cyanoalkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy; or R3c, R3d together with the nitrogen atom, to which they are bound may form a 4-, 5-, 6- or 7- membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R3e, R3f independently of each other are selected from the group consisting of hydrogen, d-Ce-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7- cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl,
Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
R3e, R3f together with the nitrogen atom, to which they are bound may form a 4-, 5-, 6- or 7- membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; R¾ is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-
C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two
aforementioned radicals are unsubstituted or partially or completely halogenated, Ci- C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci- C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R3h is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two
aforementioned radicals are unsubstituted or partially or completely halogenated, Ci- C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylcarbonyl, a radical C(0)Rk, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
R¾, R3h together with the nitrogen atom, to which they are bound may form a 4-, 5-, 6- or 7- membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3- C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci- C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Z1, phenyl-0-Ci-C6-alkyl, phenyl-N(R23)-Ci-Ce-alkyl, phenyl-S(0)n-Ci-C6-alkyl, heterocyclyl-Z1, heterocyclyl- N(R23)-Ci-C6-alkyl, heterocyclyl-O-Ci-Ce-alkyl, heterocyclyl-S(0)n-Ci-C6-alkyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups , which are identical or different and selected from the group consisting of cyano, halogen, nitro, thiocyanato, Ci-Ce-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C(0)OR23, C(0)N(R23)2, OR23, N(R23)2, S(0)nR24, S(0)2OR23, S(0)2N(R23)2, and R230-Ci-C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2- C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl; is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl; is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6- alkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Z1, phenyl-0-Ci-C6-alkyl, phenyl-N(R23)-Ci-Ce-alkyl, phenyl-S(0)n-Ci-C6-alkyl, heterocyclyl-Z1, heterocyclyl- N(R23)-Ci-C6-alkyl, heterocyclyl-O-Ci-Ce-alkyl, heterocyclyl-S(0)n-Ci-C6-alkyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups , which are identical or different and selected from the group consisting of cyano, halogen, nitro, thiocyanato, Ci-Ce-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C(0)OR23, C(0)N(R23)2, OR23, N(R23)2, S(0)nR24, S(0)2OR23, S(0)2N(R23)2, and R230-Ci-C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; is 0, 1 or 2; is 0, 1 or 2; has the meanings of R3c. In particular, in compounds I, R3 is not nitro and R2 is Ci-C6-alkyl-S(0)n-Z2, Ci-C6-haloalkyl- S(0)n-Z2, C3-C6-cycloalkyl-S(0)n-Z2, heterocyclyl-Z2a, phenyl-S(0)n-Z2, or heteroaryl-S(0)n-Z2, where the cyclic groups of the four aforementioned radicals are unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and methylsulfonyl; where Z2a is a covalent bond or Ci-C3-alkanediyl which is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl;
so that the invention relates to a compound of formula I, as depicted above, wherein Q is Q1 or Q2 or Q3 or Q4,
Figure imgf000008_0001
(Q1) (Q2) (Q3) (Q4) ; where the arrow denotes the attachment point to the remainder of the molecule;
R1 is selected from the group consisting of cyano, halogen, nitro, Ci-Cs-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci- Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C6-haloalkoxy and R1b-S(0)k-Z1; R2 is selected from the group consisting of Ci-C6-alkyl-S(0)n-Z2, Ci-C6-haloalkyl-S(0)n-Z2, C3- C6-cycloalkyl-S(0)n-Z2, heterocyclyl-Z2a, where heterocyclyl is a 5- or 6-membered saturated, S(0)n-containing heterocycle; phenyl-S(0)n-Z2, and heteroaryl-S(0)n-Z2, where the cyclic groups of the four aforementioned radicals are unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy and methylsulfonyl;
R3 is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, hydroxy- Z3, d-Ce-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-Cio-cycloalkyl-Z3, C3-C6-cycloalkenyl-Z3, C3-Cio-cycloalkoxy-Z3, C3-Cio-cycloalkyl-Ci-C2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4- cyanoalkyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, Cs-Cs-haloalkynyl, Ci-Cs-alkoxy-Z3, Ci-Cs- haloalkoxy-Z3, Ci-C4-alkoxy-Ci-C4-alkoxy-Z3, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z3, C2-C8- alkenyloxy-Z3, C2-C8-alkynyloxy-Z3, C2-C8-haloalkenyloxy-Z3, Cs-Cs-haloalkynyloxy-Z3, R3b-S(0)k-Z3, R3c-C(0)-Z3, R3dO-C(0)-Z3, R3dO-N=CH-Z3, R3eR3fN-C(0)-Z3, R¾R3hN-Z3, R22C(0)0-Z3, R25OC(0)0-Z3, (R22)2NC(0)0-Z3, R25S(0)20-Z3, R22OS(0)2-Z3,
(R22)2NS(0)2-Z3, R25OC(0)N(R22)-Z3, (R22)2NC(0)N(R22)-Z3, (R22)2NS(0)2N(R22)-Z3, (OH)2P(0)-Z3, (Ci-C4-alkoxy)2P(0)-Z3, phenyl-Z3a, and heterocyclyl-Z3a, where
heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where cyclic groups in phenyl-Z3a and heterocyclyl-Z3a are unsubstituted or substituted by 1 , 2, 3 or 4 groups R21 which are identical or different; R4 is selected from the group consisting of hydrogen, halogen, cyano-Z1, Ci-Cs-alkyl, nitro,
C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C2-C8- alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, C1-C3- alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkoxy-Z1, Ci-C4-alkylthio-Ci-C4-alkylthio-Z1 , C2-C6-alkenyloxy, C2-C6- alkynyloxy, C C6-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4- alkoxy-Z1, R1b-S(0)k-Z1, phenoxy-Z1 and heterocyclyloxy-Z1, where heterocyclyloxy is an oxygen-bound 5- or 6- membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11 which are identical or different;
R5 is halogen, cyano-Z1, nitro, Ci-Cs-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, C1-C3- alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, Ci-Cs- alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C4-alkylthio-Ci-C4- alkyl, Ci-C4-alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6- haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z1, R1b-S(0)k-Z1, phenoxy-Z1 and heterocyclyloxy-Z1, where heterocyclyloxy is an oxygen-bound 5- or 6- membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11 which are identical or different;
R6 is selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci- C4-alkyl, where the C3-C7-cycloalkyl groups of the two aforementioned radicals are unsub- stituted or partially or completely halogenated; Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C4-alkyl, Rb-S(0)n-Ci-C3-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; 1, R21, independently of each other, are selected from the group consisting of cyano, halogen, nitro, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4- alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy, C3-C7-cycloalkoxy and Ci-C6-haloalkoxy, or two radicals R21 bound to the same carbon atom together may form a group =0;
Z1, Z3, independently of each other, are selected from the group consisting of a covalent bond and Ci-C4-alkanediyl;
Z2 is Ci-C3-alkanediyl,
which is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl; is a covalent bond or Ci-C3-alkanediyl,
where the Ci-C3-alkanediyl group is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of Ci C4-alkyl and Ci-C4-haloalkyl; is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, 0-Ci-C4- alkanediyl, Ci-C4-alkanediyl-0 and Ci-C4-alkanediyl-0-Ci-C4-alkanediyl;
Rb, R1b, R3b, independently of each other, are selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C1-C6- alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S(0)n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci- C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci-C6-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy;
R3d is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C1-C6- alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S(0)n-Ci-C4-alkyl, Ci-C4-alkylamino-Ci- C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci-C6-cyanoalkyl, phenyl and benzyl, where phe- nyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
R3c and R3d, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6- or 7- membered, saturated or unsaturated heterocyclic radical which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; R3e, R3f, independently of each other, are selected from the group consisting of hydrogen, C1-C6- alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4- alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or sub- stituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
R3e and R3f, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6- or 7- membered, saturated or unsaturated heterocyclic radical which may carry as a ring mem- ber a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R¾ is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkylsulfonyl, Ci-C4-alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and select- ed from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and
Ci-C4-haloalkoxy; R3h is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci- C4-alkylsulfonyl, Ci-C4-alkylcarbonyl, a radical C(0)Rk, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or R39 and R3h, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6- or 7- membered, saturated or unsaturated heterocyclic radical which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R22 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Cs-Ce-cycloalkyl-Ci-Ce-alkoxy-Ci-Ce-alkyl, phenyl-Z1, phenyl-O-d-Ce-alkyl, phenyl-N(R23)- d-Ce-alkyl, phenyl-S(0)n-Ci-C6-alkyl, heterocyclyl-Z1, heterocyclyl-N(R23)-Ci-C6-alkyl, heterocyclyl-0-Ci-C6-alkyl, and heterocyclyl-S(0)n-Ci-C6-alkyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of cyano, halogen, nitro, thiocyanato, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl,
C(0)OR23, C(0) N(R23)2, OR23, N(R23)2, S(0)nR24, S(0)2OR23, S(0)2N(R23)2, and R230-Ci- C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; R23 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl;
R24 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl;
R25 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci- Ce-alkoxy-d-Ce-alkyl, phenyl-Z1, phenyl-O-d-Ce-alkyl, phenyl-N(R23)-Ci-Ce-alkyl, phenyl- S(0)n-Ci-C6-alkyl, heterocyclyl-Z1, heterocyclyl-N(R23)-Ci-C6-alkyl, heterocyclyl-0-d-C6- alkyl, and heterocyclyl-S(0)n-Ci-C6-alkyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of cyano, halogen, nitro, thiocyanato, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C(0)OR23, C(0)N(R23)2,
OR23, N(R23)2, S(0)nR24, S(0)2OR23, S(0)2N(R23)2, and R230-Ci-C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; k is 0, 1 or 2; n is 0, 1 or 2; and
Rk independently has the meanings of R3c; or a N-oxide or an agriculturally suitable salt thereof.
The compounds of the present invention, i.e. the compounds of formula I and their agriculturally suitable salts, are particularly useful for controlling unwanted vegetation. Therefore, the invention also relates to the use of a compound of formula I or an agriculturally suitable salt thereof or of a composition comprising at least one compound of formula I or an agriculturally suitable salt thereof for combating or controlling unwanted vegetation.
The invention also relates to a composition comprising at least one compound of formula I, or a salt thereof, and at least one auxiliary. In particular, the invention relates to an agricultural composition comprising at least one compound of formula I or an agriculturally suitable salt thereof, and at least one auxiliary customary for crop protection formulations.
The present invention also relates to a method for combating or controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound of formula I or a salt thereof, to act on unwanted plants, their seed and/or their habitat.
Depending on the substitution pattern, the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures. Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group. The term "stereoisomer(s)" encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
Depending on the substitution pattern, the compounds of formula I may be present in the form of their tautomers. Hence the invention also relates to the tautomers of compounds of formula I and the stereoisomers and salts of said tautomers. The present invention moreover relates to compounds as defined herein, wherein one or more of the atoms depicted in formula I have been replaced by its stable, preferably nonradioactive isotope (e.g., hydrogen by deuterium, 12C by 13C, 14N by 15N, 160 by 180) and in particular wherein at least one hydrogen atom has been replaced by a deuterium atom. Of course, the compounds according to the invention contain more of the respective isotope than this naturally occurs and thus is anyway present in the compounds of formula I.
The compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention in- eludes both amorphous and crystalline compounds of formula I, their enantiomers or diastere- omers, mixtures of different crystalline states of the respective compound of formula I, its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.
Salts of the compounds of the present invention are preferably agriculturally suitable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
Useful agriculturally suitable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the herbicidal action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, C1-C4- hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isoprop- ylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetrame- thylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4- alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensul- fate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The term "undesired vegetation" ("weeds") is understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any). Weeds, in the broadest sense, are plants considered undesirable in a particular location. The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn- Cm indicates in each case the possible number of carbon atoms in the group.
The term "halogen" denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
The term "partially or completely halogenated" will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. A partially or completely halogenated radical is termed below also "halo-radical". For example, partially or completely halogenated alkyl is also termed haloalkyi.
The term "alkyl" as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylamino, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyi) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, generally from 1 to 8 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms. Examples of Ci-C4- alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl (sec-butyl), isobutyl and tert-butyl. Examples for Ci-C6-alkyl are, apart those mentioned for Ci-C4-alkyl, 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 and 1 -ethyl-2-methylpropyl. Examples for Ci-Cs-alkyl are, apart those mentioned for Ci-C6-alkyl, n-heptyl, 1 -methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5- methylhexyl, 1 -ethyl pentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1 -methylheptyl, 2-methylheptyl, 1 -ethylhexyl, 2-ethylhexyl, 1 ,2-dimethylhexyl, 1 -propylpentyl and 2-propylpentyl. Examples for Ci-Cio-alkyl are, apart those mentioned for Ci-Cs-alkyl, nonyl, decyl, 2-propylheptyl and 3- propylheptyl.
The term "alkylene" (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is re- placed by one further binding site, thus forming a bivalent moiety. Ci-C2-Alkylene or C1-C2- alkanediyl is a linear or branched divalent alkyl radical having 1 or 2 carbon atoms. Examples are -CH2-, -CH2CH2- and -CH(CH3)-. Ci-C3-Alkylene or Ci-C3-alkanediyl is a linear or branched divalent alkyl radical having 1 , 2 or 3 carbon atoms. Examples are -CH2-, -CH2CH2-, -CH(CH3)-, -CH2CH2CH2-, -CH(CH3)CH2-, -CH2CH(CH3)- and -C(CH3)2-. Ci-C4-Alkylene or Ci-C4-alkanediyl is a linear or branched divalent alkyl radical having 1 , 2, 3 or 4 carbon atoms. Examples are -CH2-, -CH2CH2-, -CH(CH3)-, -CH2CH2CH2-, -CH(CH3)CH2-, -CH2CH(CH3)-, -C(CH3)2-,
-CH2CH2CH2CH2-, -CH(CH3)CH2CH2-, -CH2CH2CH(CH3)-, -C(CH3) 2CH2-, and -CH2C(CH3)2-.
The term "haloalkyi" as used herein (and in the haloalkyi moieties of other groups comprising a haloalkyi group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms ("Ci-Cs-haloalkyl"), frequently from 1 to 6 carbon atoms ("C1-C6- haloalkyl"), more frequently 1 to 4 carbon atoms ("Ci-C4-haloalkyl"), wherein the hydrogen at- oms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from Ci-C4-haloalkyl, more preferably from Ci-C2-haloalkyl, more preferably from halomethyl, in particular from Ci-C2-fluoroalkyl. Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like. Examples for Ci-C2-fluoroalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, pentafluoroethyl, and the like. Examples for Ci-C2-haloalkyl are, apart those mentioned for Ci-C2-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chloro- fluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 2-chloroethyl, 2,2,- dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 1 -bromoethyl, and the like. Examples for Ci-C4-haloalkyl are, apart those mentioned for Ci-C2-haloalkyl, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1 ,1 ,1 -trifl uoroprop-2-yl , 3-chloropropyl, 4-chlorobutyl and the like.
The term "cyanoalkyl" as used herein refers to straight-chain or branched alkyl groups having 1 to 4 ("Ci-C4-cyanoalkyl") or 1 to 6 ("Ci-C6-cyanoalkyl) carbon atoms (as mentioned above), where 1 or 2, preferably 1 , of the hydrogen atoms in these groups are replaced by a cyano (CN) group. Examples are cyanomethyl, 1 -cyanoethyl, 2-cyanoethyl, 1 -cyanopropyl, 2- cyanopropyl, 3-cyanopropyl, 1 -cyanobutyl, 2-cyanobutyl, 3-cyanobutyl, 4-cyanobutyl and the like.
The term "cycloalkyi" as used herein (and in the cycloalkyi moieties of other groups comprising a cycloalkyi group, e.g. cycloalkoxy and cycloalkylalkyi) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms ("C3-Cio-cycloalkyl"), preferably 3 to 7 carbon atoms ("C3-C7-cycloalkyl") or in particular 3 to 6 carbon atoms ("C3-C6- cycloalkyl"). Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.1 .1 ]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl. Preferably, the term cycloalkyi denotes a monocyclic saturated hydrocarbon radical.
The term "halocycloalkyl" as used herein (and in the halocycloalkyl moieties of other groups comprising an halocycloalkyl group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are 1 - and 2- fluorocyclopropyl, 1 ,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1 - and 2-chlorocyclopropyl, 1 ,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1 -,2- and 3-fluorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1 -,2- and 3-chlorocyclopentyl, 1 ,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl and the like.
The term "cycloalkyl-alkyl" used herein denotes a cycloalkyi group, as defined above, which is bound to the remainder of the molecule via an alkylene group (or inversely expressed, it denotes an alkyl group, as described above, in which one hydrogen atom is replaced by a cycloalkyl group, as defined above). The term "C3-C7-cycloalkyl-Ci-C4-alkyl" refers to a C3-C7- cycloalkyl group as defined above which is bound to the remainder of the molecule via a C1-C4- alkyl group, as defined above. Examples are cyclopropylmethyl, cyclopropylethyl, cyclo- propylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentyl methyl, cyclopen- tylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, cycloheptylme- thyl, cycloheptylethyl, cycloheptylpropyl and the like. The term "C3-C6-cycloalkyl-Ci-C6-alkyl" refers to a C3-C6-cycloalkyl group as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C6-alkyl group, as defined above. Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentyl methyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl and the like.
The term "alkenyl" as used herein denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 8 ("C2-C8-alkenyl"), preferably 2 to 6 carbon atoms ("C2-C6-alkenyl"), in particular 2 to 4 carbon atoms ("C2-C4-alkenyl"), and a double bond in any position, for example C2-C4-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl, 1 - methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 - methyl-2-propenyl or 2-methyl-2-propenyl; C2-C6-alkenyl, such as ethenyl, 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, 1 -ethyl-2-methyl-2-propenyl and the like, or C2-Cs-alkenyl, such as the radicals mentioned for C2-C6-alkenyl and additionally 1 -heptenyl, 2-heptenyl, 3-heptenyl, 1 -octenyl, 2-octenyl, 3-octenyl, 4-octenyl and the positional isomers thereof.
The term "haloalkenyl" as used herein, which may also be expressed as "alkenyl which is substituted by halogen", and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 8 ("C2-C8-haloalkenyl") or 2 to 6 ("C2-C6-haloalkenyl") or 2 to 4 ("C2-C4-haloalkenyl") carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
The term "alkynyl" as used herein denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 ("C2-C8-alkynyl"), frequently 2 to 6 ("C2-C6-alkynyl"), pref- erably 2 to 4 carbon atoms ("C2-C4-alkynyl") and a triple bond in any position, for example C2- C4-alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2- propynyl and the like, C2-C6-alkynyl, such as ethynyl, 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, 1 -ethyl-1 -methyl-2-propynyl and the like.
The term "haloalkynyl" as used herein, which is also expressed as "alkynyl which is substituted by halogen", refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 3 to 8 carbon atoms ("Cs-Cs-haloalkynyl"), frequently 3 to 6 ("C3-C6-haloalkynyl"), preferabyl 3 to 4 carbon atoms ("C3-C4-haloalkynyl"), and a triple bond in any position (as men- tioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
The term "cycloalkenyl" used herein denotes a monocyclic partially unsaturated, non- aromatic hydrocarbon radical. Examples for C3-C6-cycloalkenyl are cycloprop-1 -en-1 -yl, cyclo- prop-1 -en-3-yl, cyclobut-1 -en-1 -yl, cyclobut-1 -en-3-yl, cyclooct-1 -en-1 -yl, cyclopent-1 -en-1 -yl, cyclopent-1 -en-3-yl, cyclopent-1 -en-4-yl, cyclopenta-1 ,3-dien-1 -yl, cyclopenta-1 ,3-dien-2-yl, cy- clopenta-1 ,3-dien-5-yl, cyclohex-1 -en-1 -yl, cyclohex-1 -en-3-yl, cyclohex-1 -en-4-yl, cyclohexa- 1 ,3-dien-1 -yl, cyclohexa-1 ,3-dien-2-yl, cyclohexa-1 ,3-dien-5-yl, cyclohexa-1 ,4-dien-1 -yl and cy- clohexa-1 ,4-dien-3-yl.
The term "alkoxy" as used herein denotes in each case a straight-chain or branched alkyl group usually having from 1 to 8 carbon atoms ("d-Cs-alkoxy"), frequently from 1 to 6 carbon atoms ("Ci-C6-alkoxy"), preferably 1 to 4 carbon atoms ("Ci-C4-alkoxy"), which is bound to the remainder of the molecule via an oxygen atom. Ci-C2-Alkoxy is methoxy or ethoxy. C1-C4- Alkoxy is additionally, for example, n-propoxy, 1 -methylethoxy (isopropoxy), butoxy,
1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy). Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 - dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethyl butoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1 -ethyl-1 -methylpropoxy or 1 -ethyl-2-methylpropoxy. Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof. The term "haloalkoxy" as used herein denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 8 carbon atoms ("Ci-Cs-haloalkoxy"), frequently from 1 to 6 carbon atoms ("Ci-C6-haloalkoxy"), preferably 1 to 4 carbon atoms ("C1-C4- haloalkoxy"), more preferably 1 to 3 carbon atoms ("Ci-C3-haloalkoxy"), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms. Ci-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2CI, OCHC , OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2- chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC2F5. Ci-C4-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2- difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2- bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -(CH2F)-2-fluoroethoxy, 1 -(CH2CI)-2-chloroethoxy, 1 -(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. Ci-C6-Haloalkoxy is addi- tionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, unde- cafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluo- rohexoxy.
The term "alkenyloxy" denotes an alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Alkenyloxy is a C2-C6-alkenyl group, as de- fined above, attached via an oxygen atom to the remainder of the molecule. C2-Cs-Alkenyloxy is a C2-C8-alkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
The term "haloalkenyloxy" denotes a haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Haloalkenyloxy is a C2-C6-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C8- Haloalkenyloxy is a C2-C8-haloalkenyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
The term "alkynyloxy" denotes an alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Alkynyloxy is a C2-C6-alkynyl group, as de- fined above, attached via an oxygen atom to the remainder of the molecule. C2-Cs-Alkynyloxy is a C2-C8-alkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
The term "haloalkynyloxy" denotes a haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C6-Haloalkynyloxy is a C2-C6-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. C2-C8- Haloalkynyloxy is a C2-Cs-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule. Cs-Cs-Haloalkynyloxy is a Cs-Cs-haloalkynyl group, as defined above, attached via an oxygen atom to the remainder of the molecule.
The term "alkoxyalkyl" as used herein denotes in each case alkyl usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. The term "Ci-C4-alkoxy-Ci-C4-alkyl" as used herein, refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above. "Ci-C6-alkoxy-Ci-C6-alkyl" is a C1-C6- alkyl group, as defined above, in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are CH2OCH3, CH2-OC2H5, n-propoxymethyl, CH2-OCH(CH3)2, n- butoxymethyl, (l -methylpropoxy)-methyl, (2-methylpropoxy)methyl, CH2-OC(CH3)3, 2-
(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2-(1 -methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1 -methylpropoxy)-ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1 ,1 -dimethylethoxy)-ethyl, 2-(methoxy)- propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl, 2-(1 -methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-(1 -methylpropoxy)-propyl, 2-(2-methylpropoxy)-propyl, 2-(1 ,1 -dimethylethoxy)-propyl, 3- (methoxy)-propyl, 3-(ethoxy)-propyl, 3-(n-propoxy)-propyl, 3-(1 -methylethoxy)-propyl, 3-(n- butoxy)-propyl, 3-(1 -methylpropoxy)-propyl, 3-(2-methylpropoxy)-propyl, 3-(1 ,1 -dimethylethoxy)- propyl, 2-(methoxy)-butyl, 2-(ethoxy)-butyl, 2-(n-propoxy)-butyl, 2-(1 -methylethoxy)-butyl, 2-(n- butoxy)-butyl, 2-(1 -methylpropoxy)-butyl, 2-(2-methyl-propoxy)-butyl, 2-(1 ,1 -dimethylethoxy)- butyl, 3-(methoxy)-butyl, 3-(ethoxy)-butyl, 3-(n-propoxy)-butyl, 3-(1 -methylethoxy)-butyl, 3-(n- butoxy)-butyl, 3-(1 -methylpropoxy)-butyl, 3-(2-methylpropoxy)-butyl, 3-(1 ,1 -dimethylethoxy)- butyl, 4-(methoxy)-butyl, 4-(ethoxy)-butyl, 4-(n-propoxy)-butyl, 4-(1 -methylethoxy)-butyl, 4-(n- butoxy)-butyl, 4-(1 -methylpropoxy)-butyl, 4-(2-methylpropoxy)-butyl, 4-(1 ,1 -dimethylethoxy)- butyl and the like.
The term "haloalkoxy-alkyl" as used herein denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. Examples are fluoromethoxymethyl, difluoro- methoxymethyl, trifluoromethoxymethyl, 1 -fluoroethoxymethyl, 2-fluoroethoxymethyl, 1 ,1 - difluoroethoxymethyl, 1 ,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl, 1 ,1 ,2- trifluoroethoxymethyl, 1 ,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethox- ymethyl, 1 -fluoroethoxy-1 -ethyl, 2-fluoroethoxy-1 -ethyl, 1 ,1 -difluoroethoxy-1 -ethyl, 1 ,2- difluoroethoxy-1 -ethyl, 2,2-difluoroethoxy-1 -ethyl, 1 ,1 ,2-trifluoroethoxy-1 -ethyl, 1 ,2,2- trifluoroethoxy-1 -ethyl, 2,2,2-trifluoroethoxy-1 -ethyl, pentafluoroethoxy-1 -ethyl, 1 -fluoroethoxy-2- ethyl, 2-fluoroethoxy-2-ethyl, 1 ,1 -difluoroethoxy-2 -ethyl, 1 ,2-difluoroethoxy-2-ethyl, 2,2- difluoroethoxy-2-ethyl, 1 ,1 ,2-trifluoroethoxy-2-ethyl, 1 ,2,2-trifluoroethoxy-2-ethyl, 2,2,2- trifluoroethoxy-2-ethyl, pentafluoroethoxy-2-ethyl, and the like.
The term "alkoxy-alkoxy" as used herein, refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by another alkoxy group, as defined above. The term "Ci- C4-alkoxy-Ci-C4-alkoxy" as used herein, refers to an alkoxy group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above. Examples are methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, n-butoxymethoxy, sec-butoxymethoxy, isobutoxymethoxy, tert-butoxymethoxy, 1 - methoxyethoxy, 1 -ethoxyethoxy, 1 -propoxyethoxy, 1 -isopropoxyethoxy, 1 -n-butoxyethoxy, 1 - sec-butoxyethoxy, 1 -isobutoxyethoxy, 1 -tert-butoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2- propoxyethoxy, 2-isopropoxyethoxy, 2-n-butoxyethoxy, 2-sec-butoxyethoxy, 2-isobutoxyethoxy, 2-tert-butoxyethoxy, 1 -methoxypropoxy, 1 -ethoxypropoxy, 1 -propoxypropoxy, 1 - isopropoxypropoxy, 1 -n-butoxypropoxy, 1 -sec-butoxypropoxy, 1 -isobutoxypropoxy, 1 -tert- butoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxy, 2-isopropoxypropoxy, 2-n-butoxypropoxy, 2-sec-butoxypropoxy, 2-isobutoxypropoxy, 2-tert-butoxypropoxy, 3- methoxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypropoxy, 3-n- butoxypropoxy, 3-sec-butoxypropoxy, 3-isobutoxypropoxy, 3-tert-butoxypropoxy and the like.
The term "haloalkoxy-alkoxy" denotes an alkoxy group, wherein one of the hydrogen atoms is replaced by an alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in one or in both alkoxy moieties) are replaced by halogen atoms. Ci-C4-Haloalkoxy-Ci-C4-alkoxy is a Ci-C4-alkoxy group, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in one or in both alkoxy moieties) are replaced by halogen atoms. Examples are difluoromethoxymethoxy (CHF2OCH2), trifluoromethoxymethoxy, 1 - difluoromethoxyethoxy, 1 -trifluoromethoxyethoxy, 2-difluoromethoxyethoxy, 2- trifluoromethoxyethoxy, difluoro-methoxy-methoxy (CH3OCF2), 1 ,1 -difluoro-2-methoxyethoxy, 2,2-difluoro-2-methoxyethoxy and the like.
"Cycloalkoxy" denotes a cycloalkyi group, as defined above, bound to the remainder of the molecule via an oxygen atom. Examples of C3-C7-cycloalkoxy comprise cyclopropoxy, cy- clobutoxy, cyclopentoxy, cyclohexoxy and cycloheptoxy. Examples of C3-Cio-cycloalkoxy comprise cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cy- clononoxy and cyclodecoxy.
The term "cycloalkyl-alkoxy" as used herein, refers to an alkoxy group, as defined above, where one hydrogen atom is replaced by a cycloalkyi group, as defined above. The term "C3- Cio-cycloalkyl-Ci-C2-alkoxy" as used herein, refers to an alkoxy group having 1 or 2 carbon atoms, as defined above, where one hydrogen atom is replaced by a C3-Cio-cycloalkyl group, as defined above. Examples are cyclpropylmethoxy, cyclopropylethoxy, cyclobutylmethoxy, cyclo- butylethoxy, cyclopentylmethoxy, cyclopentylethoxy, cyclohexylmethoxy, cyclohexylethoxy, cy- cloheptylmethoxy, cycloheptylethoxy, cyclooctylmethoxy, cyclooctylethoxy, cyclononylmethoxy, cyclononylethoxy, cyclodecylmethoxy and cyclodecylethoxy.
The term "cycloalkyl-alkoxy-alkyl" as used herein, refers to an alkyl group, as defined above, wherein one hydrogen atom is replaced by an alkoxy group, as defined above, where in turn in the alkoxy group one hydrogen atom is replaced by a cycloalkyi group, as defined above. The term "C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl" as used herein, refers to an alkyl group having 1 to 6 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci- C6-alkoxy group, as defined above, where in this alkoxy group, in turn, one hydrogen atom is replaced by a C3-C6-cycloalkyl group, as defined above.
The term "alkylthio" (also alkylsulfanyl, "alkyl-S" or "alkyl-S(0)k" (wherein k is 0)) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 8 carbon atoms ("Ci-Cs-alkylthio"), frequently comprising 1 to 6 carbon atoms ("Ci-C6-alkylthio"), preferably 1 to 4 carbon atoms ("Ci-C4-alkylthio"), which is attached via a sulfur atom at any position in the alkyl group. Ci-C2-Alkylthio is methylthio or ethylthio. Ci-C4-Alkylthio is additionally, for example, n-propylthio, 1 -methylethylthio (iso- propylthio), butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 - dimethylethylthio (tert-butylthio). Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 - methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2- dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 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 or 1-ethyl-2-methylpropylthio. Ci-Cs-Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
The term "haloalkylthio" as used herein refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine. Ci-C2-Haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2CI, SCHCI2, SCC , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2- fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2- trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2- fluoroethylthio, 2,2,2-trichloroethylthio or SC2F5. Ci-C4-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio,
2- chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio,
3- bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH2-C2F5, SCF2-C2F5, 1 - (CH2F)-2-fluoroethylthio, 1 -(CH2CI)-2-chloroethylthio, 1 -(CH2Br)-2-bromoethylthio,
4- fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,
5- iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio,
6- iodohexylthio or dodecafluorohexylthio.
The terms "alkylsulfinyl" and "alkyl-S(0)k" (wherein k is 1 ) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group. For exam- pie, the term "Ci-C2-alkylsulfinyl" refers to a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C4-alkylsulfinyl" refers to a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term "Ci-C6-alkylsulfinyl" refers to a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. Ci-C2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. Ci-C4-alkylsulfinyl is additionally, for example, n-propylsulfinyl,
1 -methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2- methylpropylsulfinyl (isobutylsulfinyl) or 1 ,1 -dimethylethylsulfinyl (tert-butylsulfinyl). C1-C6- alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2- methylbutylsulfinyl, 3-methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 -ethylpropylsulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2- methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1 ,1 -dimethylbutylsulfinyl,
1 .2- dimethylbutylsulfinyl, 1 ,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,
2.3- dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1 -ethylbutylsulf inyl , 2-ethylbutylsulfinyl, 1 ,1 ,2- trimethylpropylsulfinyl, 1 ,2,2-trimethylpropylsulfinyl, 1 -ethyl-1 -methylpropylsulfinyl or 1 -ethyl-2- methylpropylsulfinyl.
The terms "alkylsulfonyl" and "alkyl-S(0)k" (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C2-alkylsulfonyl" refers to a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C4-alkylsulfonyl" refers to a Ci-C4-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. The term "Ci-C6-alkylsulfonyl" refers to a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group. Ci-C2-alkylsulfonyl is methyl- sulfonyl or ethylsulfonyl. Ci-C4-alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1 -methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1 -methylpropylsulfonyl (sec- butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert- butylsulfonyl). Ci-C6-alkylsulfonyl is additionally, for example, pentylsulfonyl,
1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 -ethylpropylsulfonyl, hexylsulfonyl, 1 - methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl,
1 .1 - dimethylbutylsulfonyl, 1 ,2-dimethylbutylsulfonyl, 1 ,3-dimethylbutylsulfonyl,
2.2- dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl,
1 - ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1 ,1 ,2-trimethylpropylsulfonyl,
1 ,2,2-trimethylpropylsulfonyl, 1 -ethyl-1 -methylpropylsulfonyl or 1 -ethyl-2-methylpropylsulfonyl.
The term "alkylthio-alkyl" as used herein, refers to a straight-chain or branched alkyl group, as defined above, where one hydrogen atom is replaced by an alkylthio group, as defined above. The term "Ci-C4-alkylthio-Ci-C4-alkyl" as used herein, refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkylthio group, as defined above. Examples are methylthiomethyl, ethyl- thiomethyl, propylthiomethyl, isopropylthiomethyl, n-butylthiomethyl, sec-butylthiomethyl, isobu- tylthiomethyl, tert-butylthiomethyl, 1 -methylthioethyl, 1 -ethylthioethyl, 1 -propylthioethyl, 1 - isopropylthioethyl, 1 -n-butylthioethyl, 1 -sec-butylthioethyl, 1 -isobutylthioethyl, 1 -tert- butylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-propylthioethyl, 2-isopropylthioethyl, 2-n- butylthioethyl, 2-sec-butylthioethyl, 2-isobutylthioethyl, 2-tert-butylthioethyl, 1 -methylthiopropyl, 1 -ethylthiopropyl, 1 -propylthiopropyl, 1 -isopropylthiopropyl, 1 -n-butylthiopropyl, 1 -sec- butylthiopropyl, 1 -isobutylthiopropyl, 1 -tert-butylthiopropyl, 2-methylthiopropyl, 2-ethylthiopropyl,
2- propylthiopropyl, 2-isopropylthiopropyl, 2-n-butylthiopropyl, 2-sec-butylthiopropyl, 2- isobutylthiopropyl, 2-tert-butylthiopropyl, 3-methylthiopropyl, 3-ethylthiopropyl, 3- propylthiopropyl, 3-isopropylthiopropyl, 3-n-butylthiopropyl, 3-sec-butylthiopropyl, 3- isobutylthiopropyl, 3-tert-butylthiopropyl and the like.
The term "alkylthio-alkylthio" as used herein, refers to an alkylthio group, as defined above, where one hydrogen atom is replaced by an alkylthio group, as defined above. The term "Ci-C4-alkylthio-Ci-C4-alkylthio" as used herein, refers to an alkylthio group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkylthio group, as defined above. Examples are methylthiomethylthio, ethylthiomethylthio, propylthiomethylthio, isopropylthiomethylthio, n-butylthiomethylthio, sec-butylthiomethylthio, isobutylthiomethylthio, tert-butylthiomethylthio, 1 -methylthioethylthio, 1 -ethylthioethylthio, 1 -propylthioethylthio, 1 - isopropylthioethylthio, 1 -n-butylthioethylthio, 1 -sec-butylthioethylthio, 1 -isobutylthioethylthio, 1 - tert-butylthioethylthio, 2-methylthioethylthio, 2-ethylthioethylthio, 2-propylthioethylthio, 2- isopropylthioethylthio, 2-n-butylthioethylthio, 2-sec-butylthioethylthio, 2-isobutylthioethylthio, 2- tert-butylthioethylthio, 1 -methylthiopropylthio, 1 -ethylthiopropylthio, 1 -propylthiopropylthio, 1 - isopropylthiopropylthio, 1 -n-butylthiopropylthio, 1 -sec-butylthiopropylthio, 1 - isobutylthiopropylthio, 1 -tert-butylthiopropylthio, 2-methylthiopropylthio, 2-ethylthiopropylthio, 2- propylthiopropylthio, 2-isopropylthiopropylthio, 2-n-butylthiopropylthio, 2-sec-butylthiopropylthio,
2- isobutylthiopropylthio, 2-tert-butylthiopropylthio, 3-methylthiopropylthio, 3-ethylthiopropylthio,
3- propylthiopropylthio, 3-isopropylthiopropylthio, 3-n-butylthiopropylthio, 3-sec- butylthiopropylthio, 3-isobutylthiopropylthio, 3-tert-butylthiopropylthio and the like.
The term "alkylamino" as used herein denotes in each case a group R*HN-, wherein R* is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms ("C1-C6- alkylamino"), preferably 1 to 4 carbon atoms("Ci-C4-alkylamino") or 1 to 3 carbon atoms ("C1-C3- alkylamino"). Examples for Ci-C3-alkylamino are methylamino, ethylamino, n-propylamino and isopropylamino. Examples of Ci-C4-alkylamino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, iso-butylamino and tert-butylamino.
The term "dialkylamino" as used herein denotes in each case a group R*R°N-, wherein R* and R°, independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms ("di-(Ci-C6-alkyl)-amino"), preferably 1 to 4 carbon atoms ("di- (Ci-C4-alkyl)-amino") or 1 to 3 carbon atoms ("di-(Ci-C3-alkyl)-amino"). Examples of a di-(Ci-C6- alkyl)-amino group are dimethylamino, diethylamino, dipropylamino, dibutylamino, methyl-ethyl- amino, methyl-propyl-amino, methyl-isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl-isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and the like.
The term "alkylamino-alkyl" denotes an alkyl group, as defined above, wherein one hydro- gen atom is replaced by an alkylamino group, as defined above. Ci-C4-alkylamino-Ci-C4-alkyl is a Ci-C4-alkyl group, as defined above, wherein one hydrogen atom is replaced by a C1-C4- alkylamino group, as defined above. Examples are methylaminomethyl, 1 -(methylamino)-ethyl,
2- (methylamino)-ethyl, 1 -(methylamino)-propyl, 2-(methylamino)-propyl, 3-(methylamino)-propyl, 1 -(methylamino)-prop-2-yl, 2-(methylamino)-prop-2-yl, 1 -(methylamino)-butyl, 2-(methylamino)- butyl, 3-(methylamino)-butyl, 4-(methylamino)-butyl, ethylaminomethyl, 1 -(ethylamino)-ethyl, 2- (ethylamino)-ethyl, 1 -(ethylamino)-propyl, 2-(ethylamino)-propyl, 3-(ethylamino)-propyl, 1 - (ethylamino)-prop-2-yl, 2-(ethylamino)-prop-2-yl, 1-(ethylamino)-butyl, 2-(ethylamino)-butyl, 3- (ethylamino)-butyl, 4-(ethylamino)-butyl, propylaminomethyl, 1 -(propylamino)-ethyl, 2- (propylamino)-ethyl, 1 -(propylamino)-propyl, 2-(propylamino)-propyl, 3-(propylamino)-propyl, 1 - (propylamino)-prop-2-yl, 2-(propylamino)-prop-2-yl, 1 -(propylamino)-butyl, 2-(propylamino)-butyl,
3- (propylamino)-butyl, 4-(propylamino)-butyl, butylaminomethyl, 1 -(butylamino)-ethyl, 2- (butylamino)-ethyl, 1 -(butylamino)-propyl, 2-(butylamino)-propyl, 3-(butylamino)-propyl, 1 - (butylamino)-prop-2-yl, 2-(butylamino)-prop-2-yl, 1-(butylamino)-butyl, 2-(butylamino)-butyl, 3- (butylamino)-butyl, 4-(butylamino)-butyl and the like.
The term "dialkylamino-alkyl" denotes an alkyl group, as defined above, wherein one hydrogen atom is replaced by a dialkylamino group, as defined above. Di-(Ci-C4-alkyl)-amino-Ci- C4-alkyl is a Ci-C4-alkyl group, as defined above, wherein one hydrogen atom is replaced by a di-(Ci-C4-alkyl)-amino group, as defined above. Examples are dimethylaminomethyl, 1 - (dimethylamino)-ethyl, 2-(dimethylamino)-ethyl, 1 -(dimethylamino)-propyl, 2-(dimethylamino)- propyl, 3-(dimethylamino)-propyl, 1 -(dimethylamino)-butyl, 2-(dimethylamino)-butyl, 3- (dimethylamino)-butyl, 4-(dimethylamino)-butyl, (ethylmethylamino)-methyl, 1 - (ethylmethylamino)-ethyl, 2-(ethylmethylamino)-ethyl, 1 -(ethylmethylamino)-propyl, 2- (ethylmethylamino)-propyl, 3-(ethylmethylamino)-propyl, 1 -(ethylmethylamino)-butyl, 2- (ethylmethylamino)-butyl, 3-(ethylmethylamino)-butyl, 4-(ethylmethylamino)-butyl, (diethyla- mino)-methyl,1 -(diethylamino)-ethyl, 2-(diethylamino)-ethyl, 1 -(diethylamino)-propyl, 2- (diethylamino)-propyl, 3-(diethylamino)-propyl, 1 -(diethylamino)-butyl, 2-(diethylamino)-butyl, 3- (diethylamino)-butyl, 4-(diethylamino)-butyl, (dipropylamino)-methyl,1 -(dipropylamino)-ethyl, 2- (dipropylamino)-ethyl, 1 -(dipropylamino)-propyl, 2-(dipropylamino)-propyl, 3-(dipropylamino)- propyl, 1 -(dipropylamino)-butyl, 2-(dipropylamino)-butyl, 3-(dipropylamino)-butyl, 4- (dipropylamino)-butyl, (dibutylamino)-methyl,1 -(dibutylamino)-ethyl, 2-(dibutylamino)-ethyl, 1 - (dibutylamino)-propyl, 2-(dibutylamino)-propyl, 3-(dibutylamino)-propyl, 1 -(dibutylamino)-butyl, 2- (dibutylamino)-butyl, 3-(dibutylamino)-butyl, 4-(dibutylamino)-butyl and the like.
The substituent "oxo" replaces a Chb group by a C(=0) group.
The suffix "-carbonyl" in a group denotes in each case that the group is bound to the remainder of the molecule via a carbonyl C=0 group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl.
The term "alkylcarbonyl" denotes an alkyl group, as defined above, attached via a carbonyl [C(=0)] group to the remainder of the molecule. Ci-C3-Alkylcarbonyl is a Ci-C3-alkyl group, as defined above, attached via a carbonyl [C(=0)] group to the remainder of the molecule. C1-C4- Alkylcarbonyl is a Ci-C4-alkyl group, as defined above, attached via a carbonyl [C(=0)] group to the remainder of the molecule. Examples for Ci-C3-alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl and isopropylcarbonyl. Examples for C1-C4- alkylcarbonyl are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl n-butylcarbonyl and the like.
The term "aryl" as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon rad- ical such as phenyl or naphthyl, in particular phenyl.
The term "het(ero)aryl" as used herein refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrim- idyl and the like.
Heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl contain one or more heteroatoms as ring members, i.e. atoms different from carbon. In the terms of the present invention, these heteroatoms are N, O and S, where N and S can also be present as oxidized heteroatom groups, namely as NO, SO or SO2. Thus, in the terms of the present invention, rings termed as heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl contain one or more heteroatoms and/or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO2 as ring members.
If not specified otherwise, the heterocyclic rings or heterocyclyl may be saturated, partially unsaturated or maximally unsaturated.
Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximally unsaturated 5- or 6-membered heteromonocyclic rings are generally aromatic. Exceptions are maximally unsaturated 6-membered rings containing O, S, SO and/or SO2 as ring members, such as pyran and thiopyran, which are not aromatic. Par- tially unsaturated rings (in terms of the present invention often simply termed just as "unsaturated rings") contain less than the maximum number of C-C and/or C-N and/or N-N double bond(s) allowed by the ring size.
The heterocyclic rings or heterocyclyl or heteroaromatic rings or heteroaryl or hetaryl may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
The term "3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1 , 2, 3 or 4 heteroatoms as ring members selected from the groups consisting of N, O and S" as used herein denotes monocyclic or bicyclic radicals, the monocyclic or bicyclic radicals being saturated, unsaturated or aromatic where N can optionally be oxidized, i.e. in the form of an N-oxide, and S can also optionally be oxidized to various oxidation states, i.e. as SO or SO2. An aromatic bicyclic heterocycle is an 8-, 9- or 10-membered bicyclic heterocycle consisting of a 5- or 6-membered heteroaromatic ring which is fused to a phenyl ring or to another 5- or 6-membered heteroaromatic ring. The heterocycle may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
Examples of a 3-, 4-, 5- or 6-membered monocyclic saturated heterocycle include:
oxirane-2-yl, aziridine-1 -yl, aziridine-2-yl, oxetan-2-yl, azetidine-1 -yl, azetidine-2-yl, azetidine-3- yl, thietane-1 -yl, thietan-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahy- drothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1 -yl, imidazolidin-2-yl, imidazoli- din-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxa- zolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, 1 ,2,4- oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-1 -yl, 1 ,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1 ,3-dioxan-5-yl, 1 ,4-dioxan-2-yl, piperidin-1 -yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-3-yl, hexahydro- pyridazin-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, pi- perazin-1 -yl, piperazin-2-yl, 1 ,3,5-hexahydrotriazin-1 -yl, 1 ,3,5-hexahydrotriazin-2-yl and
1 ,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1 -oxothiomorpholin-2-yl, 1 -oxothiomorpholin-3-yl, 1 - oxothiomorpholin-4-yl, 1 ,1 -dioxothiomorpholin-2-yl, 1 ,1 -dioxothiomorpholin-3-yl, 1 ,1 - dioxothiomorpholin-4-yl and the like.
Examples of a 5- or 6-membered monocyclic partially unsaturated heterocycle include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin- 3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2- isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4- isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3- isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3- dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4- yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol- 4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-
4- yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydro- pyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrim- idinyl, di- or tetrahydropyrazinyl, 1 ,3, 5-di- or tetrahydrotriazin-2-yl and 1 ,2, 4-di- or tetrahydrotria- zin-3-yl.
A 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring is e.g. a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring. Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3- pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,
5- thiazolyl, 1 -imidazolyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-1 -yl, 1 ,3,4-triazol-2-yl, 2- pyridinyl, 3-pyridinyl, 4-pyridinyl, 1 -oxopyridin-2-yl, 1 -oxopyridin-3-yl, 1 -oxopyridin-4-yl,3- pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include benzofuranyl, benzothienyl, indolyl, indazolyl, ben- zimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, iso- chinolinyl, purinyl, 1 ,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.
Heterocyclyl in heterocyclyl-Z2a in the definition of R2 is a 5- or 6-membered saturated, S(0)n-containing heterocycle. Generally, it contains 1 or 2 S(0)n groups as ring member(s). Examples therefor are tetrahydrothien-2-yl, tetrahydrothien-3-yl, 1 -oxo-tetrahydrothien-2-yl, 1 -oxo- tetrahydrothien-3-yl, 1 ,1 -dioxotetrahydrothien-2-yl, 1 ,1 -dioxotetrahydrothien-3-yl, tetrahydrothi- opyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 1 -oxo-tetrahydrothiopyran-2-yl, 1 -oxo-tetrahydrothiopyran-3-yl, 1 -oxo-tetrahydrothiopyran-4-yl, 1 , 1 -dioxo-tetrahydrothiopyran-2- yl, 1 ,1 -dioxo-tetrahydrothiopyran-3-yl, 1 ,1 -dioxo-tetrahydrothiopyran-4-yl, 1 ,2-dithiolan-3-yl, 1 ,2- dithiolan-4-yl, 1 ,3-dithiolan-2-yl, 1 ,3-dithiolan-4-yl, 1 ,2-dithian-3-yl, 1 ,2-dithian-4-yl, 1 ,3-dithian-2- yl, 1 ,3-dithian-4-yl, 1 ,4-dithian-2-yl and the like.
If two radicals bound on the same nitrogen atom (for example R3c and R3d or R3e and R3f or R¾ and R3h) together with the nitrogen atom, to which they are bound, form a 4-, 5-, 6- or 7- membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N, this is for example azetidin-1 -yl pyrrolidine -yl, pyrazolidin-1 -yl, imidazolidin-1 -yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, iso- thiazolidin-2-yl, [1 ,2,3]-triazolidin-1 -yl, [1 ,2,3]-triazolidin-2-yl, [1 ,2,4]-triazolidin-1 -yl, [1 ,2,4]- triazolidin-4-yl, [1 ,2,3]-oxadiazolidin-2-yl, [1 ,2,3]-oxadiazolidin-3-yl, [1 ,2,5]-oxadiazolidin-2-yl, [1 ,2,4]-oxadiazolidin-2-yl, [1 ,2,4]-oxadiazolidin-4-yl, [1 ,3,4]-oxadiazolidin-3-yl, [1 ,2,3]- thiadiazolidin-2-yl, [1 ,2,3]- thiadiazolidin-3-yl, [1 ,2,5]-thiadiazolidin-2-yl, [1 ,2,4]-thiadiazolidin-2-yl, [1 ,2,4]-thiadiazolidin-4-yl, [1 ,3,4]-thiadiazolidin-3-yl, piperdin-1 -yl, piperazin-1 -yl, morpholin-4-yl, thiomorpholin-4-yl, 1 -oxothiomorpholin-4-yl, 1 ,1 -dioxothiomorpholin-4-yl, azepan-1 -yl, 1 ,4- diazepan-1 -yl, pyrrolin-1 -yl, pyrazolin-1 -yl, imidazolin-1 -yl, oxazolin-3-yl, isoxazolin-2-yl, thia- zolin-3-yl, isothiazolin-2-yl, 1 ,2-dihydropyridin-1 -yl, 1 ,2,3,4-tetrahydropyridin-1 -yl, 1 ,2,5,6- tetrahydropyridin-1 -yl, 1 ,2-dihydropyridazin, 1 ,6-dihydropyridazin, 1 ,2,3,4-tetrahydropyridazin-1 - yl, 1 ,2,5,6-tetrahydropyridazin-1 -yl, 1 ,2-dihydropyrimidin, 1 ,6-dihydropyrimidin, 1 ,2,3,4- tetrahydropyrimidin-1 -yl, 1 ,2,5,6-tetrahydropyrimidin-1 -yl, 1 ,2-dihydropyrazin-1 -yl, 1 ,2,3,4- tetrahydropyrazin-1 -yl, 1 ,2,5,6-tetrahydropyrazin-1-yl, pyrrol-1 -yl, pyrazol-1 -yl, imidazol-1 -yl, [1 ,2,3]-1 H-triazol-1 -yl, [1 ,2,3]-2H-triazol-2-yl, [1 ,2,4]-1 H-triazol-1 -yl and [1 ,2,4]-4H-triazol-4-yl. The remarks made below as to preferred embodiments of the variables (substituents) of the compounds of formula I are valid on their own as well as preferably in combination with each other, as well as in combination with the stereoisomers, salts, or tautomers thereof.
The remarks made below concerning preferred embodiments of the variables further are valid on their own as well as preferably in combination with each other concerning the com- pounds of formulae I, where applicable, as well as concerning the uses and methods according to the invention and the composition according to the invention.
Preferred compounds according to the invention are compounds of formula I or a stereoisomer, or salt thereof, wherein the salt is an agriculturally suitable salt. Particularly preferred compounds according to the invention are compounds of formula I or a salt thereof, especially an agriculturally suitable salt thereof.
According to one embodiment of the invention the variable Q in the compounds of formula
Figure imgf000028_0001
(Q1:
Herein, the arrow represents the binding site of the variable Q1 conjugated to the remaining part of the compound of formula I. Compounds of formula I wherein Q is Q1 have the following formula I. A, where the variables R1, R2, R3, R4 and R6 are as defined herein:
Figure imgf000028_0002
According to another embodiment of the invention the variable Q in the compounds of formula I is Q2:
Figure imgf000029_0001
(Q2)
Herein, the arrow represents the binding site of the variable Q2 conjugated to the remaining part of the compound of formula I. Compounds of formula I wherein Q is Q2 have the following formula I.B, where the variables R1, R2, R3, R4 and R6 are as defined herein:
Figure imgf000029_0002
According to another embodiment of the invention the variable Q in the compounds of formula I is Q3:
Figure imgf000029_0003
(Q3)
Herein, the arrow represents the binding site of the variable Q3 conjugated to the remaining part of the compound of formula I. Compounds of formula I wherein Q is Q3 have the follow- ing formula I.C, where the variables R1, R2, R3, R4 and R6 are as defined herein:
Figure imgf000029_0004
According to another embodiment of the invention the variable Q in the compounds of formula I is Q4:
Figure imgf000029_0005
(Q4)
Herein, the arrow represents the binding site of the variable Q4 conjugated to the remaining part of the compound of formula I. Compounds of formula I wherein Q is Q4 have the following formula I.D, where the variables R1, R2, R3, R4 and R6 are as defined herein:
Figure imgf000030_0001
In particular, Q is Q1. Preferred compounds according to the invention are compounds of formula I, wherein R1 is selected from the group consisting of cyano, halogen, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C6-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy- Z1, R1b-S(0)k-Z1, where k and Z1 are as defined herein and where R1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl. In this context Z1 is in particular a covalent bond.
More preferably, R1 is selected from halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z1 and R1b-S(0)k-Z1, where k and Z1 are as defined herein and where R1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl. In this context Z1 is in particular a covalent bond.
In particular, R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl. More particularly, R1 is F, CI, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3 or CH2OCH2CH2OCH3, and specifically R1 is F, CI, Br, I, nitro, CH3, SCH3 or SO2CH3. More specifically, R1 is halogen (i.e. F, CI, Br or I), even more specifically CI or Br, and very specifically CI.
As a matter of course, in R2, the radicals Ci-C6-alkyl-S(0)n-Z2, Ci-C6-haloalkyl-S(0)n-Z2, C3-C6- cycloalkyl-S(0)n-Z2, heterocyclyl-Z2a, phenyl-S(0)n-Z2 and heteroaryl-S(0)n-Z2are bound via the bridging group Z2 or Z2a to the remainder of the molecule; i.e. to the oxygen atom.
Preferred compounds according to the invention are compounds of formula I , wherein R2 is Ci- C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, preferably from the group consisting of halogen and Ci-C4-haloalkyl; and specifically from halogen.
More preferably, R2 is Ci-C3-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, preferably from the group consisting of halogen and Ci-C4-haloalkyl; and specifically from halogen.
Specifically, R2 is H3C-S(0)n-Z2 or phenyl-S(0)n-Z2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen. Very specifically, R2 is H3C-S(0)n-Z2 or phenyl-S(0)n-Z2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from F and CI.
In another specific embodiment, R2 is phenyl-S(0)n-Z2, wherein the phenyl ring is substituted by Ci-C4-haloalkyl, preferably by Ci-C2-haloalkyl, specifically by CF3.
According to the present invention, Z2 is Ci-C3-alkanediyl,
which is unsubstituted or substituted by 1 , 2, 3 or 4 groups,
which are identical or different and selected from the group consisting of C|-C4-alkyl and d-C4-haloalkyl.
Preferably Z2 is Ci-C2-alkanediyl, which is unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of C|-C4-alkyl and C C4-haloalkyl;
more preferably Ci-C2-alkanediyl which is unsubstituted;
e.g. d-alkanediyl which is unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of C|-C4-alkyl and d-C4-haloalkyl; d-alkanediyl which is unsubstituted being preferred;
even more preferably however unsubstituted d-alkanediyl; specifically CH2CH2. In R2, especially in R2 being d-C6-alkyl-S(0)n-Z2, d-C6-haloalkyl-S(0)n-Z2, d-d-cycloalkyl- S(0)n-Z2 or heteroaryl-S(0)n-Z2, the index n is in particular 0.
Thus, R2 is more preferably d-d-alkyl-S-Z2 or phenyl-S(0)n-Z2 with n being 0, 1 or 2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group con- sisting of halogen, d-d-alkyl, d-d-haloalkyl and d-d-alkoxy, preferably from the group consisting of halogen and d-d-haloalkyl; and specifically from halogen; where Z2 has one the above general or, in particular, one of the above preferred meanings.
Even more preferably, R2 is d-d-alkyl-S-Z2 or phenyl-S(0)n-Z2 with n being 0, 1 or 2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, d-d-alkyl, d-d-haloalkyl and d-d-alkoxy, preferably from the group consisting of halogen and d-d-haloalkyl; and specifically from halogen; where Z2 has one the above general or, in particular, one of the above preferred meanings.
In particular, R2 is Ci-d-alkyl-S-CH2CH2 or phenyl-S(0)n-CH2CH2 with n being 0, 1 or 2, where- in the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group consisting of halogen, d-d-alkyl, d-d-haloalkyl and d-d-alkoxy, preferably from the group consisting of halogen and d-d-haloalkyl; and specifically from halogen, and is more particularly d-d-alkyl-S-ChbChb or phenyl-S(0)n-CH2CH2 with n being 0, 1 or 2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group consisting of halo- gen, d-d-alkyl, d-d-haloalkyl and d-d-alkoxy, preferably from the group consisting of halogen and d-d-haloalkyl; and specifically from halogen. In an alternatively preferred embodiment, R2 is C3-C6-cycloalkyl-S(0)n-Z2, more preferably C3- C6-cycloalkyl-S-Z2, in particular Cs-Ce-cycloalkyl-S-ChbCI-b and specifically cyclopropyl-S-
In an alternatively preferred embodiment, R2 is heterocyclyl-Z2a, where heterocyclyl is a 5- or 6- membered saturated heterocycle which contains one S(0)n group as ring member, where Z2a has one of the above general or, in particular, one of the below preferred meanings. More preferably, R2 is heterocyclyl-Z2a, where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S atom as ring member; where Z2a has one of the above general or, in particular, one of the below preferred meanings.
Z2a is preferably a bond or unsubstitueted Ci-C2-alkanediyl, in particular a bond or Chb; and is specifically a bond.
Thus, in an alternatively more preferred embodiment, R2 is heterocyclyl-Z2a, where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S(0)n group as ring member, where Z2a is a bond or unsubstitueted Ci-C2-alkanediyl, in particular a bond or Chb; and is specifically a bond. More particularly, R2 is heterocyclyl-Z2a, where heterocyclyl is a 5- or 6- membered saturated heterocycle which contains one S atom as ring member; where Z2a is a bond or unsubstitueted Ci-C2-alkanediyl, in particular a bond or Chb; and is specifically a bond. Specifically, R2 is heterocyclyl-Z2a, where heterocyclyl is a 6-membered saturated heterocycle which contains one S atom as ring member; where Z2a is a bond or CH2; and is specifically a bond.
Preferred compounds according to the invention are compounds of formula I, wherein R3 is selected from the group consisting of hydrogen, cyano, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-alkenyloxy, C2-C4- alkynyloxy or R3b-S(0)k, where the variables k and R3b have one of the herein defined mean- ings; in particular, R3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, or R3b-S(0)k, where the variables k and R3b have one of the herein defined meanings.
More preferably, R3 is selected from the group consisting of hydrogen, halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkyl-S(0), Ci-C4-haloalkyl-S(0), Ci-C4-alkyl-S(0)2, and Ci-C4-haloalkyl-S(0)2.
In particular, R3 is selected from the group consisting of halogen, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl and more particularly from halogen and Ci-C4-alkylsulfonyl. Specifically R3 is selected from the group consisting of from halogen (i.e. CI, F, Br, I) and S(0)2CH3, and more specifically from halogen; even more specifically from CI, Br and I, and very specifically from CI and Br. In the context of R3, R3c is preferably selected from the group consisting of Ci-C6-alkyl, C3- C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, phenyl, and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
More preferably, R3c is selected from the group consisting of CrC4-alkyl, C3-C7-cycloalkyl, d- C4-haloalkyl, CrC4-alkoxy, and phenyl, where phenyl is unsubstituted or substituted by 1 or 2 groups, which are identical or different and selected from the group consisting of halogen and CrC4-alkoxy;
Herein, particularly preferably, R3c is methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr),
CHF2CH2-, CF3CH2-, CH3O-, 4-CI-phenyl, 4-CH30-phenyl, or phenyl.
In the context of R3, R3d is preferably selected from the group consisting of Ci-C6-alkyl, C3- C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, Ci-C6-haloalkyl and phenyl where phenyl is unsubstituted or substituted by 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; more preferably, R3d is selected from the group consisting of Ci-C4-alkyl, C3-C7-cycloalkyl, and Ci-C4-haloalkyl;
Herein, very particularly preferably, R3d is methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr),
Figure imgf000033_0001
or
R3c and R3d together with the nitrogen atom, to which they are bound may form a 5- or 6- membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
preferably, R3c and R3d together with the nitrogen atom, to which they are bound form N- morpholinyl, N-pyrrolidinyl or N-piperidinyl; N-morpholinyl, N-pyrrolidinyl and N-piperidinyl may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl. Preferred compounds according to the invention are compounds of formula I, wherein in R3, Z3 is Ci-C4-alkanediyl; preferably, Z3 is -CH2- or -CH2CH2-.
According to another preferred embodiment, Z3 is a covalent bond.
Preferred compounds according to the invention are compounds of formula I, wherein R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl, and C1-C2- haloalkyl.
More preferably, R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, CH3, CHF2, and CF3, in particular from hydrogen, cyano, chlorine, fluorine and CH3. Even more preferred compounds according to the invention are compounds of formula I, wherein R4 is hydrogen, chlorine or fluorine.
Most preferred compounds according to the invention are compounds of formula I, wherein R4 is hydrogen.
Preferred compounds according to the invention are compounds of formula I, wherein R5 is selected from the group consisting of CHF2, CF3 and halogen.
More preferably, R5 is halogen, in particular chlorine or fluorine, specifically fluorine. Preferred compounds according to the invention are compounds of formula I, wherein R6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl.
In particular, R6 is selected from the group consisting of Ci-C2-alkyl, Ci-C2-alkoxy-Ci-C2- alkyl, specifically from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2. Specifically, R6 is C1-C4- alkyl, more specifically Ci-C2-alkyl, and very specifically methyl.
If not specified otherwise in this context, the variables R11, R21, Z1, Z3, Z3a, Rb, R1b, R3b, R3c, R3d, R3e, R3f, R¾, R3h, Rk, n and k, independently of each other, preferably have one of the following meanings: R11 is selected from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkoxy-Ci- C4-alkoxy and Ci-C6-haloalkyloxy, more preferably from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy.
More preferably R11 is selected from the group consisting of halogen, Ci-C4-alkyl, C3-C6- cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy; in particular from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy; and specifically from CI, F, Br, methyl, ethyl, methoxy and trifluoromethyl. R21 is selected from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkoxy-Ci- C4-alkoxy and Ci-C6-haloalkyloxy, more preferably from halogen, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy.
More preferably R21 is selected from the group consisting of halogen, Ci-C4-alkyl, C3-C6- cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy; in particular from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl and Ci-C4-alkoxy-Ci-C4-alkoxy; and specifically from CI, F, Br, methyl, ethyl, methoxy and trifluoromethyl. Z1, Z3 independently of each other are selected from a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond. Z3a is selected from a covalent bond, Ci-C2-alkanediyl, 0-Ci-C2-alkanediyl, C1-C2- alkanediyl-0 and Ci-C2-alkanediyl-0-Ci-C2-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyI, O-ethanediyI, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.
Rb, R1b, R3b independently of each other are selected from Ci-C6-alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy.
More preferably Rb, R1b, R3b independently of each other are selected from the group consisting of Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, Ci-C4-haloalkyl, C2-C4-haloalkenyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.
In particular, Rb, R1b, R3b independently of each other are selected from Ci-C4-alkyl, C1-C4- haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.
R3c, Rk independently of each other are selected from hydrogen, Ci-C6-alkyl, C3-C7- cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci- C4-alkoxy.
More preferably R3c, Rk independently of each other are selected from hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.
In particular, R3c, Rk independently of each other are selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C3-C6-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members. R3d is selected from Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6- haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl.
More preferably R3d is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C3-C6-cycloalkyl.
R3e, R3f independently of each other are selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated, Ci- C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4- haloalkyl and Ci-C4-alkoxy, or R3e and R3f together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy.
More preferably R3e, R3f independently of each other are selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl and benzyl, or R3e and R3f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
In particular, R3e, R3f independently of each other are selected from hydrogen and C1-C4- alkyl, or R3e and R3f together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups.
R¾ is selected from hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl.
More preferably R¾ is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci- C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl.
R3h is selected from hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl, benzyl and a radical C(=0)-Rk, where Rk is H, Ci-C4-alkyl, Ci-C4-haloalkyl or phenyl. More preferably R3h is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, Ci-C4-alkoxy-Ci-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, Ci-C4-alkyl, Ci- C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl; or
R39 and R3h together with the nitrogen atom, to which they are bound may form a 5-, 6 or
7-membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl and Ci-C4-haloalkyl and Ci-C4-alkoxy;
more preferably R¾ and R3h together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl and Ci-C4-haloalkyl;
and in particular, R¾ and R3h together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2 or 3 methyl groups. n and k independently of each other are 0 or 2, and in particular 2.
Also preferably n is 0.
Particularly preferred are compounds of formula I, wherein the variables R1 and R3 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z1 and R1b-S(0)k-Z1, where k and Z1 are as defined herein and where R1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl. In this context Z1 is in particular a covalent bond. In particular, R1 is selected from F, CI, Br, I, nitro, CH3, SCHs, SCFs, SO2CH3, and CH2OCH2CH2OCH3; and
R3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkyl-S(0), C1-C4- haloalkyl-S(O), Ci-C4-alkyl-S(0)2, and Ci-C4-haloalkyl-S(0)2.
In particular, R3 is selected from CI, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(0)CH3, S(0)CH2CH3, S(0)2CH3 and S(0)2CH2CH3.
Also particularly preferred are compounds of formula I, wherein the variables R1 and R3 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl, in particular from F, CI, Br, I, nitro, CH3, SCH3 and SO2CH3; and R3 is selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2- haloalkoxy, Ci-C2-alkylthio, Ci-C2-haloalkylthio, Ci-C2-alkyl-S(0), Ci-C2-haloalkyl-S(0), C1-C2- alkyl-S(0)2 and Ci-C2-haloalkyl-S(0)2, most particular from CI, Br, I, CF3, SCH3, S(0)CH3 and S(0)2CH3.
Especially preferred are compounds of formula I, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4,R5, and R6 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z1 and R1b-S(0)k-Z1, where k and Z1 are as defined herein and where R1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl. In this context Z1 is in particular a covalent bond; specifically R1 is selected from F, CI, Br, I, nitro, CH3, SCH3, SCF3, S02CH3, and CH2OCH2CH2OCH3;
R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
Z2 is Ci-C2-alkanediyl, which is unsubstitueted;
n is 0;
R3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkyl-S(0), C1-C4- haloalkyl-S(0),Ci-C4-alkyl-S(0)2, and Ci-C4-haloalkyl-S(0)2, in particular from CI, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(0)CH3, S(0)CH2CH3, S(0)2CH3 and
S(0)2CH2CH3;
R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl, and Ci-C2-haloalkyl;
R5 is selected from the group consisting of halogen, CHF2 and CF3;
R6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2. Especially preferred are compounds of formula I, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4, R5 and R6 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z1 and R1b-S(0)k-Z1, where k and Z1 are as defined herein and where R1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl. In this context Z1 is in particular a covalent bond; specifically R1 is selected from F, CI, Br, I, nitro, CH3, SCH3, SCF3, S02CH3, and CH2OCH2CH2OCH3;
R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
Z2 is Ci-C2-alkanediyl, which is unsubstitueted;
n is 0; R3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkyl-S(0), C1-C4- haloalkyl-S(0), Ci-C4-alkyl-S(0)2, and Ci-C4-haloalkyl-S(0)2, in particular from CI, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCHs, SCFs, SCHF2, S(0)CH3, S(0)CH2CH3, S(0)2CH3 and
S(0)2CH2CH3;
R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl, and Ci-C2-haloalkyl;
R5 is selected from the group consisting of halogen, CHF2 and CF3;
R6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phe- nyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2.
Especially preferred are compounds of formula I , wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3< R4, R5 and R6 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl; specifically R1 is F, CI, Br, I , nitro, CH3, SCH3 or S02CH3;
R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
Z2 is Ci-C2-alkanediyl, which is unsubstitueted;
n is 0;
R3 is selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2- haloalkoxy, Ci-C2-alkylthio, Ci-C2-haloalkylthio, Ci-C2-alkyl-S(0), Ci-C2-haloalkyl-S(0), Ci-C2- alkyl-S(0)2 and Ci-C2-haloalkyl-S(0)2, and more specifically from CI, Br, I, CF3, SCH3, S(0)CH3 and S(0)2CH3;
R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, CH3, CHF2, and CF3;
R5 is selected from the group consisting of halogen;
R6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2.
Especially preferred are compounds of formula I , wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4, R5 and R6 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl; specifically R1 is F, CI, Br, I , nitro, CH3, SCH3 or S02CH3;
R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
Z2 is Ci-C2-alkanediyl, which is unsubstitueted;
n is 0; R3 is selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2- haloalkoxy, Ci-C2-alkylthio, Ci-C2-haloalkylthio, Ci-C2-alkyl-S(0), Ci-C2-haloalkyl-S(0), C1-C2- alkyl-S(0)2 and Ci-C2-haloalkyl-S(0)2, and more specifically from CI, Br, I, CF3, SCH3, S(0)CH3 and S(0)2CH3;
R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, CH3, CHF2, and CF3;
R5 is selected from the group consisting of F;
R6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2.
Especially preferred are compounds of formula I, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4, R5 and R6 have the following meanings:
R1 is F, CI, Br, I, nitro, CH3, SCH3, SCF3, S02CH3, and CH2OCH2CH2OCH3;
R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
Z2 is Ci-C2-alkanediyl, which is unsubstitueted;
n is 0;
R3 is selected from the group consisting of CI, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(0)CH3, S(0)CH2CH3, S(0)2CH3 and S(0)2CH2CH3;
R4 is hydrogenCI or F;
R5 is selected from the group consisting of chlorine and fluorine;
R6 is selected from the group consisting of CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2. Especially preferred are compounds of formula I, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4, R5 and R6 have the following meanings:
R1 is F, CI, Br, I, nitro, CH3, SCH3, SCF3, S02CH3, and CH2OCH2CH2OCH3;
R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
Z2 is Ci-C2-alkanediyl, which is unsubstitueted;
n is 0;
R3 is selected from the group consisting of CI, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(0)CH3, S(0)CH2CH3, S(0)2CH3 and S(0)2CH2CH3;
R4 is hydrogen, chlorine or fluorine;
R5 is selected from the group consisting of halogen, CHF2 and CF3;
R6 is selected from the group consisting of CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2.
Especially preferred are compounds of formula I, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4, R5 and R6 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Z1 and R1b-S(0)k-Z1, where k and Z1 are as defined herein and where R1b is as defined above and in particular selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl. In this context Z1 is in particular a covalent bond; specifically R1 is selected from F, CI, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3, and
Figure imgf000041_0001
R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
Z2 is Ci-C2-alkanediyl, which is unsubstitueted;
n is 0;
R3 is selected from the group consisting of hydrogen, halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C -alkyl-S(0), Ci-C4-haloalkyl-S(0), Ci-C4-alkyl-S(0)2, and Ci-C4-haloalkyl-S(0)2, in particular from CI, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(0)CH3, S(0)CH2CH3, S(0)2CH3 and S(0)2CH2CH3;
R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, Ci-C2-alkyl, and Ci-C2-haloalkyl;
R5 is selected from the group consisting of chlorine and fluorine;
R6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2.
Especially preferred are compounds of formula I, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4, R5 and R6 have the following meanings:
R1 is selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-haloalkylthio and Ci-C4-alkylsulfonyl; spe- cifically R1 is F, CI, Br, I, nitro, CH3, SCH3 or S02CH3;
R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
Z2 is Ci-C2-alkanediyl, which is unsubstitueted;
n is 0
R3 is selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl, C1-C2- haloalkoxy, Ci-C2-alkylthio, Ci-C2-haloalkylthio, Ci-C2-alkyl-S(0), Ci-C2-haloalkyl- S(O), Ci-C2-alkyl-S(0)2 and Ci-C2-haloalkyl-S(0)2, and more specifically from CI, Br, I, CF3, SCH3, S(0)CH3 and S(0)2CH3;
R4 is selected from the group consisting of hydrogen, cyano, halogen, nitro, CH3, CHF2, and CF3;
R5 is selected from the group consisting of chlorine and fluorine;
R6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2.
Especially preferred are compounds of formula I, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4, R5 and R6 have the following meanings: R1 is F, CI, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3, and CH2OCH2CH2OCH3; R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from halogen;
Z2 is Ci-C2-alkanediyl, which is unsubstitueted;
n is 0;
R3 is selected from the group consisting of CI, F, Br, I , CH3, CF3, CHF2, OCF3, OCHF2,
SCH3, SCF3, SCHF2, S(0)CH3, S(0)CH2CH3, S(0)2CH3 and S(0)2CH2CH3; R4 is hydrogen, chlorine or fluorine;
R5 is selected from the group consisting of chlorine and fluorine;
R6 is selected from the group consisting of CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2.
In particular, in compounds I,
Q is Q1 ;
R1 is halogen;
R2 is Ci-C6-alkyl-S(0)n-Z2; phenyl-S(0)n-Z2, wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy; C3-C6-cycloalkyl-S(0)n-Z2; or heterocyclyl-Z2a, where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S(0)n group as ring member, where Z2, Z2a and n have one of the above general or, in particular one of the above preferred meanings;
R3 is selected from the group consisting of halogen, Ci-C4-alkylsulfonyl and C1-C4- haloalkylsulfonyl;
R4 is hydrogen;
R5 is halogen; and
R6 is Ci-C4-alkyl.
More particularly, in compounds I,
Q is Q1 ;
R1 is halogen;
R2 is Ci-C6-alkyl-S-Z2; phenyl-S(0)n-Z2, wherein n is 0, 1 or 2 and wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy; C3-C6-cycloalkyl-S-Z2; or hetero- cyclyl-Z2a, where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S atom as ring member, where Z2 is unsubstituted Ci-C2-alkanediyl and Z2a is a bond or unsubstitueted Ci-C2-alkanediyl;
R3 is selected from the group consisting of halogen and Ci-C4-alkylsulfonyl;
R4 is hydrogen;
R5 is halogen; and
R6 is Ci-C4-alkyl.
Very particularly, in compounds I, Q is Q1;
R1 is halogen;
R2 is C-i-Cs-alkyl-S-ChbCI-b; phenyl-S(0)n-CH2CH2, wherein n is 0, 1 or 2 and wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy; C3-C6-cycloalkyl-S-
Z2; or heterocyclyl-Z2a, where heterocyclyl is a 5- or 6-membered saturated heterocycle which contains one S atom as ring member, where Z2a is a bond or Chb;
R3 is selected from the group consisting of halogen and Ci-C4-alkylsulfonyl;
R4 is hydrogen;
R5 is halogen; and
R6 is Ci-C4-alkyl.
Specifically, in compounds I,
Q is Q1;
R1 is halogen;
R2 is Ci-C3-alkyl-S-CH2CH2; phenyl-S(0)n-CH2CH2, wherein n is 0, 1 or 2 and wherein the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy; cyclopropyl-S-Z2 or heterocyclyl-Z2a, where heterocyclyl is a 6-membered saturated heterocycle which con- tains one S atom as ring member, where Z2a is a bond or Chb;
R3 is selected from the group consisting of halogen and Ci-C2-alkylsulfonyl;
R4 is hydrogen;
R5 is halogen; and
R6 is Ci-C2-alkyl.
Very specifically, in compounds I,
Q is Q1;
R1 is CI or Br; in particular CI;
R2 is Ci-C3-alkyl-S-CH2CH2; phenyl-S(0)n -CH2CH2, wherein n is 0, 1 or 2 and wherein the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group consisting of halogen, Ci-C2-alkyl, Ci-C2-haloalkyl and Ci-C2-alkoxy, in particular from halogen and Ci-C2-haloalkyl; cyclopropyl-S-ChbCI-b or heterocyclyl-Z2a, where heterocyclyl is a 6-membered saturated heterocycle which contains one S atom as ring member, where Z2a is a bond or Chb, in particular a bond;
R3 is selected from the group consisting of CI, Br and methylsulfonyl;
R4 is hydrogen;
R5 is CI or F; and
R6 is Ci-C2-alkyl.
Even more specifically, in compounds I,
Q is Q1;
R1 is CI or Br; in particular CI; R2 is Ci-C3-alkyl-S-CH2CH2; phenyl-S(0)n-CH2CH2, wherein n is 0, 1 or 2 and wherein the phenyl ring is unsubstituted or substituted by 1 , 2 or 3 groups selected from the group consisting of halogen and Ci-C2-haloalkyl; or heterocyclyl-Z2a, where heterocyclyl is a 6- membered saturated heterocycle which contains one S atom as ring member (= tetrahy- drothiopyranyl), where Z2a is a bond;
R3 is selected from the group consisting of CI and Br;
R4 is hydrogen;
R5 is F; and
R6 is Ci-C2-alkyl.
Examples of preferred compounds are the individual compounds compiled in the Tables below. Moreover, the meanings mentioned below for the individual variables in the Tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.
Compounds I.A.I, wh 1, R4 is CI, R6 is methyl:
Figure imgf000044_0001
Table 1 Compounds of formula I.A.I (I.A.I.1 - I.A 1.1332) in which the combination of R1, R2, R3and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.A.II, wher 1, R4 is CI, R6 is ethyl:
Figure imgf000044_0002
Table 2 Compounds of formula I.A.II (I.A.II.1 - I.A.II.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.A.III, wherei 1, R4 is F, R6 is methyl:
Figure imgf000044_0003
Table 3 Compounds of formula I.A.III (I.A.III.1 - 1.A.I 11.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.A.IV, whe 1, R4 is F, R6 is ethyl:
Figure imgf000045_0001
Table 4 Compounds of formula I.A.IV (I.A.IV.1 - I.A.IV.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.A.V, wherei 1, R4 is H, R6 is methyl:
Figure imgf000045_0002
Table 5 Compounds of formula I.A.V (I.A.V.1 - I.A.V.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.A.VI, wherein Q is Q1, R4 is H, R6 is ethyl:
Figure imgf000045_0003
Table 6 Compounds of formula I.A.VI (I.A.VI.1 - I.A.VI.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.B.I, wherein 2, R4 is CI, R6 is methyl:
Figure imgf000045_0004
Table 7 Compounds of formula I.B.I (I.B.1.1 - 1. B.I.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.B.II, wherein Q is Q2, R4 is CI, R6 is ethyl:
Figure imgf000046_0001
Table 8 Compounds of formula I.B.II (I. B.11.1 - I.B.II.1332) in which the combination of R1, R2, R3 and R5for a compound corresponds in each case to one row of Table A;
Compounds I.B.III, wherein Q is Q2, R4 is F, R6 is methyl:
Figure imgf000046_0002
Table 9 Compounds of formula I.B.III (I.B.III.1 - I.B. III.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.B. IV, whe 2, R4 is F, R6 is ethyl:
Figure imgf000046_0003
Table 10 Compounds of formula I.B.IV (I.B.IV.1 - I.B.IV.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.B.V, wherei 2, R4 is H, R6 is methyl:
Figure imgf000046_0004
Table 1 1 Compounds of formula I.B.V (I.B.V.1 - I.B.V.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.B.VI, whe 2, R4 is H, R6 is ethyl:
Figure imgf000046_0005
Table 12 Compounds of formula I.B.VI (I.B.VI.1 - I.B.VI.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.C.I, wherei 3, R4 is CI, R6 is methyl:
Figure imgf000047_0001
Table 13 Compounds of formula I.C.I (I.C.I.1 - 1. C.I.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I. CM, whe 3, R4 is CI, R6 is ethyl:
Figure imgf000047_0002
Table 14 Compounds of formula I.C.II (I.C.II.1 - 1. CM.1332) in which the combination of R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.C.III, wherei 3, R4 is F, R6 is methyl:
Figure imgf000047_0003
Table 15 Compounds of formula I.C.III (I.C.III.1 - I.C.III.1332) in which the combination of R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I. CIV, whe 3, R4 is F, R6 is ethyl:
Figure imgf000047_0004
Table 16 Compounds of formula I.C.IV (I.C.IV.1 - I.C.IV.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.C.V, wherein Q is Q3, R4 is H, R6 is methyl:
Figure imgf000048_0001
Table 17 Compounds of formula I.C.V (I.C.V.1 - I.C.V.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.C.VI, whe 3, R4 is H, R6 is ethyl:
Figure imgf000048_0002
Table 18 Compounds of formula I.C.VI (I.C.VI.1 - I.C.VI.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.D.I, whe 4, R4 is CI, R6 is methyl
Figure imgf000048_0003
Table 19 Compounds of formula I.D.I (I.D.1.1 - 1. D.I.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.D.II, wh 4, R4 is CI, R6 is ethyl:
Figure imgf000048_0004
Table 20 Compounds of formula I.D.II (I. D.11.1 - I.D.II.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.D.III, whe 4, R4 is F, R6 is methyl:
Figure imgf000048_0005
Table 21 Compounds of formula I.D.III (I.D.III.1 - 1. D. III.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.D.IV, wh 4, R4 is F, R6 is ethyl:
Figure imgf000049_0001
Table 22 Compounds of formula I.D.IV (I.D.IV.1 - I.D.IV.1332) in which the combination of R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.D.V, whe 4, R4 is H, R6 is methyl:
Figure imgf000049_0002
Table 23 Compounds of formula I.D.V (I.D.V.1 - I.D.V.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Compounds I.D.VI, wh 4, R4 is H, R6 is ethyl:
Figure imgf000049_0003
Table 24 Compounds of formula I.D.VI (I.D.VI.1 - I.D.VI.1332) in which the combination of R1, R2, R3 and R5 for a compound corresponds in each case to one row of Table A;
Table A:
Figure imgf000049_0004
Figure imgf000049_0005
No. R1 R2 R3 R5 No. R1 R2 R3 R5
17. CI R2-17 CI F 53. CI R2-16 CI CI
18. CI R2-18 CI F 54. CI R2-17 CI CI
19. CI R2-19 CI F 55. CI R2-18 CI CI
20. CI R2-20 CI F 56. CI R2-19 CI CI
21 . CI R2-21 CI F 57. CI R2-20 CI CI
22. CI R2-22 CI F 58. CI R2-21 CI CI
23. CI R2-23 CI F 59. CI R2-22 CI CI
24. CI R2-24 CI F 60. CI R2-23 CI CI
25. CI R2-25 CI F 61 . CI R2-24 CI CI
26. CI R2-26 CI F 62. CI R2-25 CI CI
27. CI R2-27 CI F 63. CI R2-26 CI CI
28. CI R2-28 CI F 64. CI R2-27 CI CI
29. CI R2-29 CI F 65. CI R2-28 CI CI
30. CI R2-30 CI F 66. CI R2-29 CI CI
31 . CI R2-31 CI F 67. CI R2-30 CI CI
32. CI R2-32 CI F 68. CI R2-31 CI CI
33. CI R2-33 CI F 69. CI R2-32 CI CI
34. CI R2-34 CI F 70. CI R2-33 CI CI
35. CI R2-35 CI F 71 . CI R2-34 CI CI
36. CI R2-36 CI F 72. CI R2-35 CI CI
37. CI R2-37 CI F 73. CI R2-36 CI CI
38. CI R2-1 CI CI 74. CI R2-37 CI CI
39. CI R2-2 CI CI 75. CI R2-1 Br F
40. CI R2-3 CI CI 76. CI R2-2 Br F
41 . CI R2-4 CI CI 77. CI R2-3 Br F
42. CI R2-5 CI CI 78. CI R2-4 Br F
43. CI R2-6 CI CI 79. CI R2-5 Br F
44. CI R2-7 CI CI 80. CI R2-6 Br F
45. CI R2-8 CI CI 81 . CI R2-7 Br F
46. CI R2-9 CI CI 82. CI R2-8 Br F
47. CI R2-10 CI CI 83. CI R2-9 Br F
48. CI R2-1 1 CI CI 84. CI R2-10 Br F
49. CI R2-12 CI CI 85. CI R2-1 1 Br F
50. CI R2-13 CI CI 86. CI R2-12 Br F
51 . CI R2-14 CI CI 87. CI R2-13 Br F
52. CI R2-15 CI CI 88. CI R2-14 Br F No. R1 R2 R3 R5 No. R1 R2 R3 R5
89. CI R2-15 Br F 125. CI R2-14 Br CI
90. CI R2-16 Br F 126. CI R2-15 Br CI
91 . CI R2-17 Br F 127. CI R2-16 Br CI
92. CI R2-18 Br F 128. CI R2-17 Br CI
93. CI R2-19 Br F 129. CI R2-18 Br CI
94. CI R2-20 Br F 130. CI R2-19 Br CI
95. CI R2-21 Br F 131 . CI R2-20 Br CI
96. CI R2-22 Br F 132. CI R2-21 Br CI
97. CI R2-23 Br F 133. CI R2-22 Br CI
98. CI R2-24 Br F 134. CI R2-23 Br CI
99. CI R2-25 Br F 135. CI R2-24 Br CI
100. CI R2-26 Br F 136. CI R2-25 Br CI
101 . CI R2-27 Br F 137. CI R2-26 Br CI
102. CI R2-28 Br F 138. CI R2-27 Br CI
103. CI R2-29 Br F 139. CI R2-28 Br CI
104. CI R2-30 Br F 140. CI R2-29 Br CI
105. CI R2-31 Br F 141 . CI R2-30 Br CI
106. CI R2-32 Br F 142. CI R2-31 Br CI
107. CI R2-33 Br F 143. CI R2-32 Br CI
108. CI R2-34 Br F 144. CI R2-33 Br CI
109. CI R2-35 Br F 145. CI R2-34 Br CI
1 10. CI R2-36 Br F 146. CI R2-35 Br CI
1 1 1 . CI R2-37 Br F 147. CI R2-36 Br CI
1 12. CI R2-1 Br CI 148. CI R2-37 Br CI
1 13. CI R2-2 Br CI 149. CI R2-1 I F
1 14. CI R2-3 Br CI 150. CI R2-2 I F
1 15. CI R2-4 Br CI 151 . CI R2-3 I F
1 16. CI R2-5 Br CI 152. CI R2-4 I F
1 17. CI R2-6 Br CI 153. CI R2-5 I F
1 18. CI R2-7 Br CI 154. CI R2-6 I F
1 19. CI R2-8 Br CI 155. CI R2-7 I F
120. CI R2-9 Br CI 156. CI R2-8 I F
121 . CI R2-10 Br CI 157. CI R2-9 I F
122. CI R2-1 1 Br CI 158. CI R2-10 I F
123. CI R2-12 Br CI 159. CI R2-1 1 I F
124. CI R2-13 Br CI 160. CI R2-12 I F No. R1 R2 R3 R5 No. R1 R2 R3 R5
161 . CI R2-13 I F 197. CI R2-12 I CI
162. CI R2-14 I F 198. CI R2-13 I CI
163. CI R2-15 I F 199. CI R2-14 I CI
164. CI R2-16 I F 200. CI R2-15 I CI
165. CI R2-17 I F 201 . CI R2-16 I CI
166. CI R2-18 I F 202. CI R2-17 I CI
167. CI R2-19 I F 203. CI R2-18 I CI
168. CI R2-20 I F 204. CI R2-19 I CI
169. CI R2-21 I F 205. CI R2-20 I CI
170. CI R2-22 I F 206. CI R2-21 I CI
171 . CI R2-23 I F 207. CI R2-22 I CI
172. CI R2-24 I F 208. CI R2-23 I CI
173. CI R2-25 I F 209. CI R2-24 I CI
174. CI R2-26 I F 210. CI R2-25 I CI
175. CI R2-27 I F 21 1 . CI R2-26 I CI
176. CI R2-28 I F 212. CI R2-27 I CI
177. CI R2-29 I F 213. CI R2-28 I CI
178. CI R2-30 I F 214. CI R2-29 I CI
179. CI R2-31 I F 215. CI R2-30 I CI
180. CI R2-32 I F 216. CI R2-31 I CI
181 . CI R2-33 I F 217. CI R2-32 I CI
182. CI R2-34 I F 218. CI R2-33 I CI
183. CI R2-35 I F 219. CI R2-34 I CI
184. CI R2-36 I F 220. CI R2-35 I CI
185. CI R2-37 I F 221 . CI R2-36 I CI
186. CI R2-1 I CI 222. CI R2-37 I CI
187. CI R2-2 I CI 223. CI R2-1 CFs F
188. CI R2-3 I CI 224. CI R2-2 CFs F
189. CI R2-4 I CI 225. CI R2-3 CFs F
190. CI R2-5 I CI 226. CI R2-4 CFs F
191 . CI R2-6 I CI 227. CI R2-5 CFs F
192. CI R2-7 I CI 228. CI R2-6 CFs F
193. CI R2-8 I CI 229. CI R2-7 CFs F
194. CI R2-9 I CI 230. CI R2-8 CFs F
195. CI R2-10 I CI 231 . CI R2-9 CFs F
196. CI R2-1 1 I CI 232. CI R2-10 CFs F No. R1 R2 R3 R5 No. R1 R2 R3 R5
233. CI R2-1 1 CFs F 269. CI R2-10 CFs CI
234. CI R2-12 CFs F 270. CI R2-1 1 CFs CI
235. CI R2-13 CFs F 271 . CI R2-12 CFs CI
236. CI R2-14 CFs F 272. CI R2-13 CFs CI
237. CI R2-15 CFs F 273. CI R2-14 CFs CI
238. CI R2-16 CFs F 274. CI R2-15 CFs CI
239. CI R2-17 CFs F 275. CI R2-16 CFs CI
240. CI R2-18 CFs F 276. CI R2-17 CFs CI
241 . CI R2-19 CFs F 277. CI R2-18 CFs CI
242. CI R2-20 CFs F 278. CI R2-19 CFs CI
243. CI R2-21 CFs F 279. CI R2-20 CFs CI
244. CI R2-22 CFs F 280. CI R2-21 CFs CI
245. CI R2-23 CFs F 281 . CI R2-22 CFs CI
246. CI R2-24 CFs F 282. CI R2-23 CFs CI
247. CI R2-25 CFs F 283. CI R2-24 CFs CI
248. CI R2-26 CFs F 284. CI R2-25 CFs CI
249. CI R2-27 CFs F 285. CI R2-26 CFs CI
250. CI R2-28 CFs F 286. CI R2-27 CFs CI
251 . CI R2-29 CFs F 287. CI R2-28 CFs CI
252. CI R2-30 CFs F 288. CI R2-29 CFs CI
253. CI R2-31 CFs F 289. CI R2-30 CFs CI
254. CI R2-32 CFs F 290. CI R2-31 CFs CI
255. CI R2-33 CFs F 291 . CI R2-32 CFs CI
256. CI R2-34 CFs F 292. CI R2-33 CFs CI
257. CI R2-35 CFs F 293. CI R2-34 CFs CI
258. CI R2-36 CFs F 294. CI R2-35 CFs CI
259. CI R2-37 CFs F 295. CI R2-36 CFs CI
260. CI R2-1 CFs CI 296. CI R2-37 CFs CI
261 . CI R2-2 CFs CI 297. CI R2-1 HsCS(O) F
262. CI R2-3 CFs CI 298. CI R2-2 HsCS(O) F
263. CI R2-4 CFs CI 299. CI R2-3 HsCS(O) F
264. CI R2-5 CFs CI 300. CI R2-4 HsCS(O) F
265. CI R2-6 CFs CI 301 . CI R2-5 HsCS(O) F
266. CI R2-7 CFs CI 302. CI R2-6 HsCS(O) F
267. CI R2-8 CFs CI 303. CI R2-7 HsCS(O) F
268. CI R2-9 CFs CI 304. CI R2-8 HsCS(O) F No. R1 R2 R3 R5 No. R1 R2 R3 R5
305. CI R2-9 H3CS(0) F 341. CI R2-8 H3CS(0) CI
306. CI R2-10 H3CS(0) F 342. CI R2-9 H3CS(0) CI
307. CI R2-1 1 H3CS(0) F 343. CI R2-10 H3CS(0) CI
308. CI R2-12 H3CS(0) F 344. CI R2-1 1 H3CS(0) CI
309. CI R2-13 H3CS(0) F 345. CI R2-12 H3CS(0) CI
310. CI R2-14 H3CS(0) F 346. CI R2-13 H3CS(0) CI
311. CI R2-15 H3CS(0) F 347. CI R2-14 H3CS(0) CI
312. CI R2-16 H3CS(0) F 348. CI R2-15 H3CS(0) CI
313. CI R2-17 H3CS(0) F 349. CI R2-16 H3CS(0) CI
314. CI R2-18 H3CS(0) F 350. CI R2-17 H3CS(0) CI
315. CI R2-19 H3CS(0) F 351. CI R2-18 H3CS(0) CI
316. CI R2-20 H3CS(0) F 352. CI R2-19 H3CS(0) CI
317. CI R2-21 H3CS(0) F 353. CI R2-20 H3CS(0) CI
318. CI R2-22 H3CS(0) F 354. CI R2-21 H3CS(0) CI
319. CI R2-23 H3CS(0) F 355. CI R2-22 H3CS(0) CI
320. CI R2-24 H3CS(0) F 356. CI R2-23 H3CS(0) CI
321. CI R2-25 H3CS(0) F 357. CI R2-24 H3CS(0) CI
322. CI R2-26 H3CS(0) F 358. CI R2-25 H3CS(0) CI
323. CI R2-27 H3CS(0) F 359. CI R2-26 H3CS(0) CI
324. CI R2-28 H3CS(0) F 360. CI R2-27 H3CS(0) CI
325. CI R2-29 H3CS(0) F 361. CI R2-28 H3CS(0) CI
326. CI R2-30 H3CS(0) F 362. CI R2-29 H3CS(0) CI
327. CI R2-31 H3CS(0) F 363. CI R2-30 H3CS(0) CI
328. CI R2-32 H3CS(0) F 364. CI R2-31 H3CS(0) CI
329. CI R2-33 H3CS(0) F 365. CI R2-32 H3CS(0) CI
330. CI R2-34 H3CS(0) F 366. CI R2-33 H3CS(0) CI
331. CI R2-35 H3CS(0) F 367. CI R2-34 H3CS(0) CI
332. CI R2-36 H3CS(0) F 368. CI R2-35 H3CS(0) CI
333. CI R2-37 H3CS(0) F 369. CI R2-36 H3CS(0) CI
334. CI R2-1 H3CS(0) CI 370. CI R2-37 H3CS(0) CI
335. CI R2-2 H3CS(0) CI 371. CI R2-1 H3CS(0)2 F
336. CI R2-3 H3CS(0) CI 372. CI R2-2 H3CS(0)2 F
337. CI R2-4 H3CS(0) CI 373. CI R2-3 H3CS(0)2 F
338. CI R2-5 H3CS(0) CI 374. CI R2-4 H3CS(0)2 F
339. CI R2-6 H3CS(0) CI 375. CI R2-5 H3CS(0)2 F
340. CI R2-7 H3CS(0) CI 376. CI R2-6 H3CS(0)2 F No. R1 R2 R3 R5 No. R1 R2 R3 R5
377. CI R2-7 H3CS(0)2 F 413. CI R2-6 HsCS(0)2 CI
378. CI R2-8 H3CS(0)2 F 414. CI R2-7 HsCS(0)2 CI
379. CI R2-9 H3CS(0)2 F 415. CI R2-8 HsCS(0)2 CI
380. CI R2-10 H3CS(0)2 F 416. CI R2-9 HsCS(0)2 CI
381 . CI R2-1 1 H3CS(0)2 F 417. CI R2-10 HsCS(0)2 CI
382. CI R2-12 H3CS(0)2 F 418. CI R2-1 1 HsCS(0)2 CI
383. CI R2-13 H3CS(0)2 F 419. CI R2-12 HsCS(0)2 CI
384. CI R2-14 H3CS(0)2 F 420. CI R2-13 HsCS(0)2 CI
385. CI R2-15 H3CS(0)2 F 421 . CI R2-14 HsCS(0)2 CI
386. CI R2-16 H3CS(0)2 F 422. CI R2-15 HsCS(0)2 CI
387. CI R2-17 H3CS(0)2 F 423. CI R2-16 HsCS(0)2 CI
388. CI R2-18 H3CS(0)2 F 424. CI R2-17 HsCS(0)2 CI
389. CI R2-19 H3CS(0)2 F 425. CI R2-18 HsCS(0)2 CI
390. CI R2-20 H3CS(0)2 F 426. CI R2-19 HsCS(0)2 CI
391 . CI R2-21 H3CS(0)2 F 427. CI R2-20 HsCS(0)2 CI
392. CI R2-22 H3CS(0)2 F 428. CI R2-21 HsCS(0)2 CI
393. CI R2-23 H3CS(0)2 F 429. CI R2-22 HsCS(0)2 CI
394. CI R2-24 H3CS(0)2 F 430. CI R2-23 HsCS(0)2 CI
395. CI R2-25 H3CS(0)2 F 431 . CI R2-24 HsCS(0)2 CI
396. CI R2-26 H3CS(0)2 F 432. CI R2-25 HsCS(0)2 CI
397. CI R2-27 H3CS(0)2 F 433. CI R2-26 HsCS(0)2 CI
398. CI R2-28 H3CS(0)2 F 434. CI R2-27 HsCS(0)2 CI
399. CI R2-29 H3CS(0)2 F 435. CI R2-28 HsCS(0)2 CI
400. CI R2-30 H3CS(0)2 F 436. CI R2-29 HsCS(0)2 CI
401 . CI R2-31 H3CS(0)2 F 437. CI R2-30 HsCS(0)2 CI
402. CI R2-32 H3CS(0)2 F 438. CI R2-31 HsCS(0)2 CI
403. CI R2-33 H3CS(0)2 F 439. CI R2-32 HsCS(0)2 CI
404. CI R2-34 H3CS(0)2 F 440. CI R2-33 HsCS(0)2 CI
405. CI R2-35 H3CS(0)2 F 441 . CI R2-34 HsCS(0)2 CI
406. CI R2-36 H3CS(0)2 F 442. CI R2-35 HsCS(0)2 CI
407. CI R2-37 H3CS(0)2 F 443. CI R2-36 HsCS(0)2 CI
408. CI R2-1 H3CS(0)2 CI 444. CI R2-37 HsCS(0)2 CI
409. CI R2-2 H3CS(0)2 CI 445. CHs R2-1 CI F
410. CI R2-3 H3CS(0)2 CI 446. CHs R2-2 CI F
41 1 . CI R2-4 H3CS(0)2 CI 447. CHs R2-3 CI F
412. CI R2-5 H3CS(0)2 CI 448. CHs R2-4 CI F No. R1 R2 R3 R5 No. R1 R2 R3 R5
449. CHs R2-5 CI F 485. CHs R2-4 CI CI
450. CHs R2-6 CI F 486. CHs R2-5 CI CI
451 . CHs R2-7 CI F 487. CHs R2-6 CI CI
452. CHs R2-8 CI F 488. CHs R2-7 CI CI
453. CHs R2-9 CI F 489. CHs R2-8 CI CI
454. CHs R2-10 CI F 490. CHs R2-9 CI CI
455. CHs R2-1 1 CI F 491 . CHs R2-10 CI CI
456. CHs R2-12 CI F 492. CHs R2-1 1 CI CI
457. CHs R2-13 CI F 493. CHs R2-12 CI CI
458. CHs R2-14 CI F 494. CHs R2-13 CI CI
459. CHs R2-15 CI F 495. CHs R2-14 CI CI
460. CHs R2-16 CI F 496. CHs R2-15 CI CI
461 . CHs R2-17 CI F 497. CHs R2-16 CI CI
462. CHs R2-18 CI F 498. CHs R2-17 CI CI
463. CHs R2-19 CI F 499. CHs R2-18 CI CI
464. CHs R2-20 CI F 500. CHs R2-19 CI CI
465. CHs R2-21 CI F 501 . CHs R2-20 CI CI
466. CHs R2-22 CI F 502. CHs R2-21 CI CI
467. CHs R2-23 CI F 503. CHs R2-22 CI CI
468. CHs R2-24 CI F 504. CHs R2-23 CI CI
469. CHs R2-25 CI F 505. CHs R2-24 CI CI
470. CHs R2-26 CI F 506. CHs R2-25 CI CI
471 . CHs R2-27 CI F 507. CHs R2-26 CI CI
472. CHs R2-28 CI F 508. CHs R2-27 CI CI
473. CHs R2-29 CI F 509. CHs R2-28 CI CI
474. CHs R2-30 CI F 510. CHs R2-29 CI CI
475. CHs R2-31 CI F 51 1 . CHs R2-30 CI CI
476. CHs R2-32 CI F 512. CHs R2-31 CI CI
477. CHs R2-33 CI F 513. CHs R2-32 CI CI
478. CHs R2-34 CI F 514. CHs R2-33 CI CI
479. CHs R2-35 CI F 515. CHs R2-34 CI CI
480. CHs R2-36 CI F 516. CHs R2-35 CI CI
481 . CHs R2-37 CI F 517. CHs R2-36 CI CI
482. CHs R2-1 CI CI 518. CHs R2-37 CI CI
483. CHs R2-2 CI CI 519. CHs R2-1 Br F
484. CHs R2-3 CI CI 520. CHs R2-2 Br F No. R1 R2 R3 R5 No. R1 R2 R3 R5
521 . CHs R2-3 Br F 557. CHs R2-2 Br CI
522. CHs R2-4 Br F 558. CHs R2-3 Br CI
523. CHs R2-5 Br F 559. CHs R2-4 Br CI
524. CHs R2-6 Br F 560. CHs R2-5 Br CI
525. CHs R2-7 Br F 561 . CHs R2-6 Br CI
526. CHs R2-8 Br F 562. CHs R2-7 Br CI
527. CHs R2-9 Br F 563. CHs R2-8 Br CI
528. CHs R2-10 Br F 564. CHs R2-9 Br CI
529. CHs R2-1 1 Br F 565. CHs R2-10 Br CI
530. CHs R2-12 Br F 566. CHs R2-1 1 Br CI
531 . CHs R2-13 Br F 567. CHs R2-12 Br CI
532. CHs R2-14 Br F 568. CHs R2-13 Br CI
533. CHs R2-15 Br F 569. CHs R2-14 Br CI
534. CHs R2-16 Br F 570. CHs R2-15 Br CI
535. CHs R2-17 Br F 571 . CHs R2-16 Br CI
536. CHs R2-18 Br F 572. CHs R2-17 Br CI
537. CHs R2-19 Br F 573. CHs R2-18 Br CI
538. CHs R2-20 Br F 574. CHs R2-19 Br CI
539. CHs R2-21 Br F 575. CHs R2-20 Br CI
540. CHs R2-22 Br F 576. CHs R2-21 Br CI
541 . CHs R2-23 Br F 577. CHs R2-22 Br CI
542. CHs R2-24 Br F 578. CHs R2-23 Br CI
543. CHs R2-25 Br F 579. CHs R2-24 Br CI
544. CHs R2-26 Br F 580. CHs R2-25 Br CI
545. CHs R2-27 Br F 581 . CHs R2-26 Br CI
546. CHs R2-28 Br F 582. CHs R2-27 Br CI
547. CHs R2-29 Br F 583. CHs R2-28 Br CI
548. CHs R2-30 Br F 584. CHs R2-29 Br CI
549. CHs R2-31 Br F 585. CHs R2-30 Br CI
550. CHs R2-32 Br F 586. CHs R2-31 Br CI
551 . CHs R2-33 Br F 587. CHs R2-32 Br CI
552. CHs R2-34 Br F 588. CHs R2-33 Br CI
553. CHs R2-35 Br F 589. CHs R2-34 Br CI
554. CHs R2-36 Br F 590. CHs R2-35 Br CI
555. CHs R2-37 Br F 591 . CHs R2-36 Br CI
556. CHs R2-1 Br CI 592. CHs R2-37 Br CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
593. CHs R2-1 I F 629. CHs R2-37 I F
594. CHs R2-2 I F 630. CHs R2-1 I CI
595. CHs R2-3 I F 631 . CHs R2-2 I CI
596. CHs R2-4 I F 632. CHs R2-3 I CI
597. CHs R2-5 I F 633. CHs R2-4 I CI
598. CHs R2-6 I F 634. CHs R2-5 I CI
599. CHs R2-7 I F 635. CHs R2-6 I CI
600. CHs R2-8 I F 636. CHs R2-7 I CI
601 . CHs R2-9 I F 637. CHs R2-8 I CI
602. CHs R2-10 I F 638. CHs R2-9 I CI
603. CHs R2-1 1 I F 639. CHs R2-10 I CI
604. CHs R2-12 I F 640. CHs R2-1 1 I CI
605. CHs R2-13 I F 641 . CHs R2-12 I CI
606. CHs R2-14 I F 642. CHs R2-13 I CI
607. CHs R2-15 I F 643. CHs R2-14 I CI
608. CHs R2-16 I F 644. CHs R2-15 I CI
609. CHs R2-17 I F 645. CHs R2-16 I CI
610. CHs R2-18 I F 646. CHs R2-17 I CI
61 1 . CHs R2-19 I F 647. CHs R2-18 I CI
612. CHs R2-20 I F 648. CHs R2-19 I CI
613. CHs R2-21 I F 649. CHs R2-20 I CI
614. CHs R2-22 I F 650. CHs R2-21 I CI
615. CHs R2-23 I F 651 . CHs R2-22 I CI
616. CHs R2-24 I F 652. CHs R2-23 I CI
617. CHs R2-25 I F 653. CHs R2-24 I CI
618. CHs R2-26 I F 654. CHs R2-25 I CI
619. CHs R2-27 I F 655. CHs R2-26 I CI
620. CHs R2-28 I F 656. CHs R2-27 I CI
621 . CHs R2-29 I F 657. CHs R2-28 I CI
622. CHs R2-30 I F 658. CHs R2-29 I CI
623. CHs R2-31 I F 659. CHs R2-30 I CI
624. CHs R2-32 I F 660. CHs R2-31 I CI
625. CHs R2-33 I F 661 . CHs R2-32 I CI
626. CHs R2-34 I F 662. CHs R2-33 I CI
627. CHs R2-35 I F 663. CHs R2-34 I CI
628. CHs R2-36 I F 664. CHs R2-35 I CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
665. CHs R2-36 I CI 701 . CHs R2-35 CFs F
666. CHs R2-37 I CI 702. CHs R2-36 CFs F
667. CHs R2-1 CFs F 703. CHs R2-37 CFs F
668. CHs R2-2 CFs F 704. CHs R2-1 CFs CI
669. CHs R2-3 CFs F 705. CHs R2-2 CFs CI
670. CHs R2-4 CFs F 706. CHs R2-3 CFs CI
671 . CHs R2-5 CFs F 707. CHs R2-4 CFs CI
672. CHs R2-6 CFs F 708. CHs R2-5 CFs CI
673. CHs R2-7 CFs F 709. CHs R2-6 CFs CI
674. CHs R2-8 CFs F 710. CHs R2-7 CFs CI
675. CHs R2-9 CFs F 71 1 . CHs R2-8 CFs CI
676. CHs R2-10 CFs F 712. CHs R2-9 CFs CI
677. CHs R2-1 1 CFs F 713. CHs R2-10 CFs CI
678. CHs R2-12 CFs F 714. CHs R2-1 1 CFs CI
679. CHs R2-13 CFs F 715. CHs R2-12 CFs CI
680. CHs R2-14 CFs F 716. CHs R2-13 CFs CI
681 . CHs R2-15 CFs F 717. CHs R2-14 CFs CI
682. CHs R2-16 CFs F 718. CHs R2-15 CFs CI
683. CHs R2-17 CFs F 719. CHs R2-16 CFs CI
684. CHs R2-18 CFs F 720. CHs R2-17 CFs CI
685. CHs R2-19 CFs F 721 . CHs R2-18 CFs CI
686. CHs R2-20 CFs F 722. CHs R2-19 CFs CI
687. CHs R2-21 CFs F 723. CHs R2-20 CFs CI
688. CHs R2-22 CFs F 724. CHs R2-21 CFs CI
689. CHs R2-23 CFs F 725. CHs R2-22 CFs CI
690. CHs R2-24 CFs F 726. CHs R2-23 CFs CI
691 . CHs R2-25 CFs F 727. CHs R2-24 CFs CI
692. CHs R2-26 CFs F 728. CHs R2-25 CFs CI
693. CHs R2-27 CFs F 729. CHs R2-26 CFs CI
694. CHs R2-28 CFs F 730. CHs R2-27 CFs CI
695. CHs R2-29 CFs F 731 . CHs R2-28 CFs CI
696. CHs R2-30 CFs F 732. CHs R2-29 CFs CI
697. CHs R2-31 CFs F 733. CHs R2-30 CFs CI
698. CHs R2-32 CFs F 734. CHs R2-31 CFs CI
699. CHs R2-33 CFs F 735. CHs R2-32 CFs CI
700. CHs R2-34 CFs F 736. CHs R2-33 CFs CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
737. CHs R2-34 CFs CI 773. CHs R2-33 HsCS(O) F
738. CHs R2-35 CFs CI 774. CHs R2-34 HsCS(O) F
739. CHs R2-36 CFs CI 775. CHs R2-35 HsCS(O) F
740. CHs R2-37 CFs CI 776. CHs R2-36 HsCS(O) F
741 . CHs R2-1 HsCS(O) F 777. CHs R2-37 HsCS(O) F
742. CHs R2-2 HsCS(O) F 778. CHs R2-1 HsCS(O) CI
743. CHs R2-3 HsCS(O) F 779. CHs R2-2 HsCS(O) CI
744. CHs R2-4 HsCS(O) F 780. CHs R2-3 HsCS(O) CI
745. CHs R2-5 HsCS(O) F 781 . CHs R2-4 HsCS(O) CI
746. CHs R2-6 HsCS(O) F 782. CHs R2-5 HsCS(O) CI
747. CHs R2-7 HsCS(O) F 783. CHs R2-6 HsCS(O) CI
748. CHs R2-8 HsCS(O) F 784. CHs R2-7 HsCS(O) CI
749. CHs R2-9 HsCS(O) F 785. CHs R2-8 HsCS(O) CI
750. CHs R2-10 HsCS(O) F 786. CHs R2-9 HsCS(O) CI
751 . CHs R2-1 1 HsCS(O) F 787. CHs R2-10 HsCS(O) CI
752. CHs R2-12 HsCS(O) F 788. CHs R2-1 1 HsCS(O) CI
753. CHs R2-13 HsCS(O) F 789. CHs R2-12 HsCS(O) CI
754. CHs R2-14 HsCS(O) F 790. CHs R2-13 HsCS(O) CI
755. CHs R2-15 HsCS(O) F 791 . CHs R2-14 HsCS(O) CI
756. CHs R2-16 HsCS(O) F 792. CHs R2-15 HsCS(O) CI
757. CHs R2-17 HsCS(O) F 793. CHs R2-16 HsCS(O) CI
758. CHs R2-18 HsCS(O) F 794. CHs R2-17 HsCS(O) CI
759. CHs R2-19 HsCS(O) F 795. CHs R2-18 HsCS(O) CI
760. CHs R2-20 HsCS(O) F 796. CHs R2-19 HsCS(O) CI
761 . CHs R2-21 HsCS(O) F 797. CHs R2-20 HsCS(O) CI
762. CHs R2-22 HsCS(O) F 798. CHs R2-21 HsCS(O) CI
763. CHs R2-23 HsCS(O) F 799. CHs R2-22 HsCS(O) CI
764. CHs R2-24 HsCS(O) F 800. CHs R2-23 HsCS(O) CI
765. CHs R2-25 HsCS(O) F 801 . CHs R2-24 HsCS(O) CI
766. CHs R2-26 HsCS(O) F 802. CHs R2-25 HsCS(O) CI
767. CHs R2-27 HsCS(O) F 803. CHs R2-26 HsCS(O) CI
768. CHs R2-28 HsCS(O) F 804. CHs R2-27 HsCS(O) CI
769. CHs R2-29 HsCS(O) F 805. CHs R2-28 HsCS(O) CI
770. CHs R2-30 HsCS(O) F 806. CHs R2-29 HsCS(O) CI
771 . CHs R2-31 HsCS(O) F 807. CHs R2-30 HsCS(O) CI
772. CHs R2-32 HsCS(O) F 808. CHs R2-31 HsCS(O) CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
809. CHs R2-32 HsCS(O) CI 845. CHs R2-31 HsCS(0)2 F
810. CHs R2-33 HsCS(O) CI 846. CHs R2-32 HsCS(0)2 F
81 1 . CHs R2-34 HsCS(O) CI 847. CHs R2-33 HsCS(0)2 F
812. CHs R2-35 HsCS(O) CI 848. CHs R2-34 HsCS(0)2 F
813. CHs R2-36 HsCS(O) CI 849. CHs R2-35 HsCS(0)2 F
814. CHs R2-37 HsCS(O) CI 850. CHs R2-36 HsCS(0)2 F
815. CHs R2-1 HsCS(0)2 F 851 . CHs R2-37 HsCS(0)2 F
816. CHs R2-2 HsCS(0)2 F 852. CHs R2-1 HsCS(0)2 CI
817. CHs R2-3 HsCS(0)2 F 853. CHs R2-2 HsCS(0)2 CI
818. CHs R2-4 HsCS(0)2 F 854. CHs R2-3 HsCS(0)2 CI
819. CHs R2-5 HsCS(0)2 F 855. CHs R2-4 HsCS(0)2 CI
820. CHs R2-6 HsCS(0)2 F 856. CHs R2-5 HsCS(0)2 CI
821 . CHs R2-7 HsCS(0)2 F 857. CHs R2-6 HsCS(0)2 CI
822. CHs R2-8 HsCS(0)2 F 858. CHs R2-7 HsCS(0)2 CI
823. CHs R2-9 HsCS(0)2 F 859. CHs R2-8 HsCS(0)2 CI
824. CHs R2-10 HsCS(0)2 F 860. CHs R2-9 HsCS(0)2 CI
825. CHs R2-1 1 HsCS(0)2 F 861 . CHs R2-10 HsCS(0)2 CI
826. CHs R2-12 HsCS(0)2 F 862. CHs R2-1 1 HsCS(0)2 CI
827. CHs R2-13 HsCS(0)2 F 863. CHs R2-12 HsCS(0)2 CI
828. CHs R2-14 HsCS(0)2 F 864. CHs R2-13 HsCS(0)2 CI
829. CHs R2-15 HsCS(0)2 F 865. CHs R2-14 HsCS(0)2 CI
830. CHs R2-16 HsCS(0)2 F 866. CHs R2-15 HsCS(0)2 CI
831 . CHs R2-17 HsCS(0)2 F 867. CHs R2-16 HsCS(0)2 CI
832. CHs R2-18 HsCS(0)2 F 868. CHs R2-17 HsCS(0)2 CI
833. CHs R2-19 HsCS(0)2 F 869. CHs R2-18 HsCS(0)2 CI
834. CHs R2-20 HsCS(0)2 F 870. CHs R2-19 HsCS(0)2 CI
835. CHs R2-21 HsCS(0)2 F 871 . CHs R2-20 HsCS(0)2 CI
836. CHs R2-22 HsCS(0)2 F 872. CHs R2-21 HsCS(0)2 CI
837. CHs R2-23 HsCS(0)2 F 873. CHs R2-22 HsCS(0)2 CI
838. CHs R2-24 HsCS(0)2 F 874. CHs R2-23 HsCS(0)2 CI
839. CHs R2-25 HsCS(0)2 F 875. CHs R2-24 HsCS(0)2 CI
840. CHs R2-26 HsCS(0)2 F 876. CHs R2-25 HsCS(0)2 CI
841 . CHs R2-27 HsCS(0)2 F 877. CHs R2-26 HsCS(0)2 CI
842. CHs R2-28 HsCS(0)2 F 878. CHs R2-27 HsCS(0)2 CI
843. CHs R2-29 HsCS(0)2 F 879. CHs R2-28 HsCS(0)2 CI
844. CHs R2-30 HsCS(0)2 F 880. CHs R2-29 HsCS(0)2 CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
881 . CHs R2-30 HsCS(0)2 CI 917. Br R2-29 CI F
882. CHs R2-31 HsCS(0)2 CI 918. Br R2-30 CI F
883. CHs R2-32 HsCS(0)2 CI 919. Br R2-31 CI F
884. CHs R2-33 HsCS(0)2 CI 920. Br R2-32 CI F
885. CHs R2-34 HsCS(0)2 CI 921 . Br R2-33 CI F
886. CHs R2-35 HsCS(0)2 CI 922. Br R2-34 CI F
887. CHs R2-36 HsCS(0)2 CI 923. Br R2-35 CI F
888. CHs R2-37 HsCS(0)2 CI 924. Br R2-36 CI F
889. Br R2-1 CI F 925. Br R2-37 CI F
890. Br R2-2 CI F 926. Br R2-1 CI CI
891 . Br R2-3 CI F 927. Br R2-2 CI CI
892. Br R2-4 CI F 928. Br R2-3 CI CI
893. Br R2-5 CI F 929. Br R2-4 CI CI
894. Br R2-6 CI F 930. Br R2-5 CI CI
895. Br R2-7 CI F 931 . Br R2-6 CI CI
896. Br R2-8 CI F 932. Br R2-7 CI CI
897. Br R2-9 CI F 933. Br R2-8 CI CI
898. Br R2-10 CI F 934. Br R2-9 CI CI
899. Br R2-1 1 CI F 935. Br R2-10 CI CI
900. Br R2-12 CI F 936. Br R2-1 1 CI CI
901 . Br R2-13 CI F 937. Br R2-12 CI CI
902. Br R2-14 CI F 938. Br R2-13 CI CI
903. Br R2-15 CI F 939. Br R2-14 CI CI
904. Br R2-16 CI F 940. Br R2-15 CI CI
905. Br R2-17 CI F 941 . Br R2-16 CI CI
906. Br R2-18 CI F 942. Br R2-17 CI CI
907. Br R2-19 CI F 943. Br R2-18 CI CI
908. Br R2-20 CI F 944. Br R2-19 CI CI
909. Br R2-21 CI F 945. Br R2-20 CI CI
910. Br R2-22 CI F 946. Br R2-21 CI CI
91 1 . Br R2-23 CI F 947. Br R2-22 CI CI
912. Br R2-24 CI F 948. Br R2-23 CI CI
913. Br R2-25 CI F 949. Br R2-24 CI CI
914. Br R2-26 CI F 950. Br R2-25 CI CI
915. Br R2-27 CI F 951 . Br R2-26 CI CI
916. Br R2-28 CI F 952. Br R2-27 CI CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
953. Br R2-28 CI CI 989. Br R2-27 Br F
954. Br R2-29 CI CI 990. Br R2-28 Br F
955. Br R2-30 CI CI 991 . Br R2-29 Br F
956. Br R2-31 CI CI 992. Br R2-30 Br F
957. Br R2-32 CI CI 993. Br R2-31 Br F
958. Br R2-33 CI CI 994. Br R2-32 Br F
959. Br R2-34 CI CI 995. Br R2-33 Br F
960. Br R2-35 CI CI 996. Br R2-34 Br F
961 . Br R2-36 CI CI 997. Br R2-35 Br F
962. Br R2-37 CI CI 998. Br R2-36 Br F
963. Br R2-1 Br F 999. Br R2-37 Br F
964. Br R2-2 Br F 1000. Br R2-1 Br CI
965. Br R2-3 Br F 1001 . Br R2-2 Br CI
966. Br R2-4 Br F 1002. Br R2-3 Br CI
967. Br R2-5 Br F 1003. Br R2-4 Br CI
968. Br R2-6 Br F 1004. Br R2-5 Br CI
969. Br R2-7 Br F 1005. Br R2-6 Br CI
970. Br R2-8 Br F 1006. Br R2-7 Br CI
971 . Br R2-9 Br F 1007. Br R2-8 Br CI
972. Br R2-10 Br F 1008. Br R2-9 Br CI
973. Br R2-1 1 Br F 1009. Br R2-10 Br CI
974. Br R2-12 Br F 1010. Br R2-1 1 Br CI
975. Br R2-13 Br F 101 1 . Br R2-12 Br CI
976. Br R2-14 Br F 1012. Br R2-13 Br CI
977. Br R2-15 Br F 1013. Br R2-14 Br CI
978. Br R2-16 Br F 1014. Br R2-15 Br CI
979. Br R2-17 Br F 1015. Br R2-16 Br CI
980. Br R2-18 Br F 1016. Br R2-17 Br CI
981 . Br R2-19 Br F 1017. Br R2-18 Br CI
982. Br R2-20 Br F 1018. Br R2-19 Br CI
983. Br R2-21 Br F 1019. Br R2-20 Br CI
984. Br R2-22 Br F 1020. Br R2-21 Br CI
985. Br R2-23 Br F 1021 . Br R2-22 Br CI
986. Br R2-24 Br F 1022. Br R2-23 Br CI
987. Br R2-25 Br F 1023. Br R2-24 Br CI
988. Br R2-26 Br F 1024. Br R2-25 Br CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
1025. Br R2-26 Br CI 1061 . Br R2-25 I F
1026. Br R2-27 Br CI 1062. Br R2-26 I F
1027. Br R2-28 Br CI 1063. Br R2-27 I F
1028. Br R2-29 Br CI 1064. Br R2-28 I F
1029. Br R2-30 Br CI 1065. Br R2-29 I F
1030. Br R2-31 Br CI 1066. Br R2-30 I F
1031 . Br R2-32 Br CI 1067. Br R2-31 I F
1032. Br R2-33 Br CI 1068. Br R2-32 I F
1033. Br R2-34 Br CI 1069. Br R2-33 I F
1034. Br R2-35 Br CI 1070. Br R2-34 I F
1035. Br R2-36 Br CI 1071 . Br R2-35 I F
1036. Br R2-37 Br CI 1072. Br R2-36 I F
1037. Br R2-1 I F 1073. Br R2-37 I F
1038. Br R2-2 I F 1074. Br R2-1 I CI
1039. Br R2-3 I F 1075. Br R2-2 I CI
1040. Br R2-4 I F 1076. Br R2-3 I CI
1041 . Br R2-5 I F 1077. Br R2-4 I CI
1042. Br R2-6 I F 1078. Br R2-5 I CI
1043. Br R2-7 I F 1079. Br R2-6 I CI
1044. Br R2-8 I F 1080. Br R2-7 I CI
1045. Br R2-9 I F 1081 . Br R2-8 I CI
1046. Br R2-10 I F 1082. Br R2-9 I CI
1047. Br R2-1 1 I F 1083. Br R2-10 I CI
1048. Br R2-12 I F 1084. Br R2-1 1 I CI
1049. Br R2-13 I F 1085. Br R2-12 I CI
1050. Br R2-14 I F 1086. Br R2-13 I CI
1051 . Br R2-15 I F 1087. Br R2-14 I CI
1052. Br R2-16 I F 1088. Br R2-15 I CI
1053. Br R2-17 I F 1089. Br R2-16 I CI
1054. Br R2-18 I F 1090. Br R2-17 I CI
1055. Br R2-19 I F 1091 . Br R2-18 I CI
1056. Br R2-20 I F 1092. Br R2-19 I CI
1057. Br R2-21 I F 1093. Br R2-20 I CI
1058. Br R2-22 I F 1094. Br R2-21 I CI
1059. Br R2-23 I F 1095. Br R2-22 I CI
1060. Br R2-24 I F 1096. Br R2-23 I CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
1097. Br R2-24 I CI 1133. Br R2-23 CFs F
1098. Br R2-25 I CI 1134. Br R2-24 CFs F
1099. Br R2-26 I CI 1135. Br R2-25 CFs F
1100. Br R2-27 I CI 1136. Br R2-26 CFs F
1101. Br R2-28 I CI 1137. Br R2-27 CFs F
1102. Br R2-29 I CI 1138. Br R2-28 CFs F
1103. Br R2-30 I CI 1139. Br R2-29 CFs F
1104. Br R2-31 I CI 1140. Br R2-30 CFs F
1105. Br R2-32 I CI 1141. Br R2-31 CFs F
1106. Br R2-33 I CI 1142. Br R2-32 CFs F
1107. Br R2-34 I CI 1143. Br R2-33 CFs F
1108. Br R2-35 I CI 1144. Br R2-34 CFs F
1109. Br R2-36 I CI 1145. Br R2-35 CFs F
1110. Br R2-37 I CI 1146. Br R2-36 CFs F
1111. Br R2-1 CFs F 1147. Br R2-37 CFs F
1112. Br R2-2 CFs F 1148. Br R2-1 CFs CI
1113. Br R2-3 CFs F 1149. Br R2-2 CFs CI
1114. Br R2-4 CFs F 1150. Br R2-3 CFs CI
1115. Br R2-5 CFs F 1151. Br R2-4 CFs CI
1116. Br R2-6 CFs F 1152. Br R2-5 CFs CI
1117. Br R2-7 CFs F 1153. Br R2-6 CFs CI
1118. Br R2-8 CFs F 1154. Br R2-7 CFs CI
1119. Br R2-9 CFs F 1155. Br R2-8 CFs CI
1120. Br R2-10 CFs F 1156. Br R2-9 CFs CI
1121. Br R2-11 CFs F 1157. Br R2-10 CFs CI
1122. Br R2-12 CFs F 1158. Br R2-11 CFs CI
1123. Br R2-13 CFs F 1159. Br R2-12 CFs CI
1124. Br R2-14 CFs F 1160. Br R2-13 CFs CI
1125. Br R2-15 CFs F 1161. Br R2-14 CFs CI
1126. Br R2-16 CFs F 1162. Br R2-15 CFs CI
1127. Br R2-17 CFs F 1163. Br R2-16 CFs CI
1128. Br R2-18 CFs F 1164. Br R2-17 CFs CI
1129. Br R2-19 CFs F 1165. Br R2-18 CFs CI
1130. Br R2-20 CFs F 1166. Br R2-19 CFs CI
1131. Br R2-21 CFs F 1167. Br R2-20 CFs CI
1132. Br R2-22 CFs F 1168. Br R2-21 CFs CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
1169. Br R2-22 CFs CI 1205. Br R2-21 HsCS(O) F
1170. Br R2-23 CFs CI 1206. Br R2-22 HsCS(O) F
1171. Br R2-24 CFs CI 1207. Br R2-23 HsCS(O) F
1172. Br R2-25 CFs CI 1208. Br R2-24 HsCS(O) F
1173. Br R2-26 CFs CI 1209. Br R2-25 HsCS(O) F
1174. Br R2-27 CFs CI 1210. Br R2-26 HsCS(O) F
1175. Br R2-28 CFs CI 1211. Br R2-27 HsCS(O) F
1176. Br R2-29 CFs CI 1212. Br R2-28 HsCS(O) F
1177. Br R2-30 CFs CI 1213. Br R2-29 HsCS(O) F
1178. Br R2-31 CFs CI 1214. Br R2-30 HsCS(O) F
1179. Br R2-32 CFs CI 1215. Br R2-31 HsCS(O) F
1180. Br R2-33 CFs CI 1216. Br R2-32 HsCS(O) F
1181. Br R2-34 CFs CI 1217. Br R2-33 HsCS(O) F
1182. Br R2-35 CFs CI 1218. Br R2-34 HsCS(O) F
1183. Br R2-36 CFs CI 1219. Br R2-35 HsCS(O) F
1184. Br R2-37 CFs CI 1220. Br R2-36 HsCS(O) F
1185. Br R2-1 HsCS(O) F 1221. Br R2-37 HsCS(O) F
1186. Br R2-2 HsCS(O) F 1222. Br R2-1 HsCS(O) CI
1187. Br R2-3 HsCS(O) F 1223. Br R2-2 HsCS(O) CI
1188. Br R2-4 HsCS(O) F 1224. Br R2-3 HsCS(O) CI
1189. Br R2-5 HsCS(O) F 1225. Br R2-4 HsCS(O) CI
1190. Br R2-6 HsCS(O) F 1226. Br R2-5 HsCS(O) CI
1191. Br R2-7 HsCS(O) F 1227. Br R2-6 HsCS(O) CI
1192. Br R2-8 HsCS(O) F 1228. Br R2-7 HsCS(O) CI
1193. Br R2-9 HsCS(O) F 1229. Br R2-8 HsCS(O) CI
1194. Br R2-10 HsCS(O) F 1230. Br R2-9 HsCS(O) CI
1195. Br R2-11 HsCS(O) F 1231. Br R2-10 HsCS(O) CI
1196. Br R2-12 HsCS(O) F 1232. Br R2-11 HsCS(O) CI
1197. Br R2-13 HsCS(O) F 1233. Br R2-12 HsCS(O) CI
1198. Br R2-14 HsCS(O) F 1234. Br R2-13 HsCS(O) CI
1199. Br R2-15 HsCS(O) F 1235. Br R2-14 HsCS(O) CI
1200. Br R2-16 HsCS(O) F 1236. Br R2-15 HsCS(O) CI
1201. Br R2-17 HsCS(O) F 1237. Br R2-16 HsCS(O) CI
1202. Br R2-18 HsCS(O) F 1238. Br R2-17 HsCS(O) CI
1203. Br R2-19 HsCS(O) F 1239. Br R2-18 HsCS(O) CI
1204. Br R2-20 HsCS(O) F 1240. Br R2-19 HsCS(O) CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
1241. Br R2-20 H3CS(0) CI 1277. Br R2-19 H3CS(0)2 F
1242. Br R2-21 H3CS(0) CI 1278. Br R2-20 H3CS(0)2 F
1243. Br R2-22 H3CS(0) CI 1279. Br R2-21 H3CS(0)2 F
1244. Br R2-23 H3CS(0) CI 1280. Br R2-22 H3CS(0)2 F
1245. Br R2-24 H3CS(0) CI 1281. Br R2-23 H3CS(0)2 F
1246. Br R2-25 H3CS(0) CI 1282. Br R2-24 H3CS(0)2 F
1247. Br R2-26 H3CS(0) CI 1283. Br R2-25 H3CS(0)2 F
1248. Br R2-27 H3CS(0) CI 1284. Br R2-26 H3CS(0)2 F
1249. Br R2-28 H3CS(0) CI 1285. Br R2-27 H3CS(0)2 F
1250. Br R2-29 H3CS(0) CI 1286. Br R2-28 H3CS(0)2 F
1251. Br R2-30 H3CS(0) CI 1287. Br R2-29 H3CS(0)2 F
1252. Br R2-31 H3CS(0) CI 1288. Br R2-30 H3CS(0)2 F
1253. Br R2-32 H3CS(0) CI 1289. Br R2-31 H3CS(0)2 F
1254. Br R2-33 H3CS(0) CI 1290. Br R2-32 H3CS(0)2 F
1255. Br R2-34 H3CS(0) CI 1291. Br R2-33 H3CS(0)2 F
1256. Br R2-35 H3CS(0) CI 1292. Br R2-34 H3CS(0)2 F
1257. Br R2-36 H3CS(0) CI 1293. Br R2-35 H3CS(0)2 F
1258. Br R2-37 H3CS(0) CI 1294. Br R2-36 H3CS(0)2 F
1259. Br R2-1 H3CS(0)2 F 1295. Br R2-37 H3CS(0)2 F
1260. Br R2-2 H3CS(0)2 F 1296. Br R2-1 H3CS(0)2 CI
1261. Br R2-3 H3CS(0)2 F 1297. Br R2-2 H3CS(0)2 CI
1262. Br R2-4 H3CS(0)2 F 1298. Br R2-3 H3CS(0)2 CI
1263. Br R2-5 H3CS(0)2 F 1299. Br R2-4 H3CS(0)2 CI
1264. Br R2-6 H3CS(0)2 F 1300. Br R2-5 H3CS(0)2 CI
1265. Br R2-7 H3CS(0)2 F 1301. Br R2-6 H3CS(0)2 CI
1266. Br R2-8 H3CS(0)2 F 1302. Br R2-7 H3CS(0)2 CI
1267. Br R2-9 H3CS(0)2 F 1303. Br R2-8 H3CS(0)2 CI
1268. Br R2-10 H3CS(0)2 F 1304. Br R2-9 H3CS(0)2 CI
1269. Br R2-1 1 H3CS(0)2 F 1305. Br R2-10 H3CS(0)2 CI
1270. Br R2-12 H3CS(0)2 F 1306. Br R2-1 1 H3CS(0)2 CI
1271. Br R2-13 H3CS(0)2 F 1307. Br R2-12 H3CS(0)2 CI
1272. Br R2-14 H3CS(0)2 F 1308. Br R2-13 H3CS(0)2 CI
1273. Br R2-15 H3CS(0)2 F 1309. Br R2-14 H3CS(0)2 CI
1274. Br R2-16 H3CS(0)2 F 1310. Br R2-15 H3CS(0)2 CI
1275. Br R2-17 H3CS(0)2 F 131 1. Br R2-16 H3CS(0)2 CI
1276. Br R2-18 H3CS(0)2 F 1312. Br R2-17 H3CS(0)2 CI No. R1 R2 R3 R5 No. R1 R2 R3 R5
1313. Br R2-18 H3CS(0)2 CI 1323. Br R2-28 H3CS(0)2 CI
1314. Br R2-19 H3CS(0)2 CI 1324. Br R2-29 H3CS(0)2 CI
1315. Br R2-20 H3CS(0)2 CI 1325. Br R2-30 H3CS(0)2 CI
1316. Br R2-21 H3CS(0)2 CI 1326. Br R2-31 H3CS(0)2 CI
1317. Br R2-22 H3CS(0)2 CI 1327. Br R2-32 H3CS(0)2 CI
1318. Br R2-23 H3CS(0)2 CI 1328. Br R2-33 H3CS(0)2 CI
1319. Br R2-24 H3CS(0)2 CI 1329. Br R2-34 H3CS(0)2 CI
1320. Br R2-25 H3CS(0)2 CI 1330. Br R2-35 H3CS(0)2 CI
1321 . Br R2-26 H3CS(0)2 CI 1331 . Br R2-36 H3CS(0)2 CI
1322. Br R2-27 H3CS(0)2 CI 1332. Br R2-37 H3CS(0)2 CI
R2-1 to R2-37 have following meanings. The indicates the attachment point to the oxygen atom.
Figure imgf000068_0001
Figure imgf000069_0001
The compounds of formula I can be prepared by standard methods of organic chemistry, e.g. by the methods described in the schemes below. The substituents, variables and indices used in the schemes are as defined above for the compounds of formula I, if not specified otherwise.
The compounds of formula I. A can be prepared analogous to Scheme 1 below. Scheme 1 :
Figure imgf000070_0001
Likewise, the compounds of formula I.B can be prepared analogous to Scheme 2 below: Scheme 2:
Figure imgf000070_0002
Likewise, the compounds of formula I.C can be prepared analogous to Scheme 3 below: Scheme 3:
Figure imgf000070_0003
(V) (N) (I.C)
Likewise, the compounds of fromula I.D can be preparedd analogous to Scheme 4 below:
Scheme 4:
Figure imgf000070_0004
5-Amino-1 -R-tetrazole compounds of formula III can be reacted with benzoyl derivatives of formula II to afford compounds of formula I. A. Likewise, 5-amino-1 -R-1 ,2,4-triazole of formula IV can be reacted with benzoyl derivatives of formula II to afford compounds of formula I.B. Likewise, 4-amino-1 ,2,5-oxadiazole compounds of formula V can be reacted with benzoyl derivatives of formula II to afford compounds of the formula I.C. Likewise, 4-amino-1 ,3,4-oxadiazole compounds of formula Va can be reacted with benzoyl derivatives of formula II to afford com- pounds of the formula I.D. Herein, X is a leaving group, such as halogen, in particular CI, an anhydride residue or an active ester residue. Especially in case of X being halogen the reaction is suitably carried out in the presence of a base. Suitable bases are for example carbonates, such as lithium, sodium or potassium carbonates, amines, such as trimethylamine or triethyla- mine, and basic N-heterocycles, such as pyridine, 2,6-dimethylpyridine or 2,4,6- trimethylpyridine. Suitable solvents are in particular aprotic solvents such as pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloroform, 1 ,2-dichlorethane, benzene, chlo- robenzene, toluene, the xylenes, dichlorobenzene, trimethylbenzene, pyridine, 2,6- dimethylpyridine, 2,4,6-trimethylpyridine, acetonitrile, diethyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, methyl tert-butylether, 1 ,4-dioxane, Ν,Ν-dimethyl formamide, N-methyl pyrroli- dinone or mixtures thereof. The starting materials are generally reacted with one another in equimolar or nearly equimolar amounts at a reaction temperature usually in the range of -20°C to 100°C and preferably in the range of -5°C to 50°C.
Alternatively, compounds of formula I can also be prepared as shown in Schemes 5, 6, 7 and 8. Reaction of 5-amino-1 -R-tetrazole of formula III with a benzoic acid derivative of formula VI yields compound I.A. Likewise, reaction of 5-amino-1 -R-1 ,2,4-triazole of formula IV with a benzoic acid derivative of formula VI yields compound I.B. Likeweise, reaction of a 4-amino- 1 ,2,5-oxadiazole compound V with a benzoic acid derivative of formula VI yields compound I.C. Likeweise, reaction of a 4-amino-1 ,3,4-oxadiazole compound Va with a benzoic acid derivative of formula VI yields compound I.D. The reaction is preferably carried out in the presence of a suitable activating agent, which converts the acid group of compound VI into an activated ester or amide. For this purpose activating agents known in the art, such as 1 ,1 ',carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 1 -ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or 2,4,6-tripropyl-1 ,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) can be employed. The activated ester or amide can be formed, depending in particular on the specific activating agent used, either in situ by contacting compound V with the activating agent in the presence of compound III or IV, or in a separate step prior to the reaction with compound III or IV. It may be advantageous, especially in cases where DCC or EDC are used as activating agent, to include further additives in the activating reaction, such as hydroxybenzotriazole (HOBt), nitrophenol, pentafluorophenol, 2,4,5-trichlorophenol or N-hydroxysuccinimide. It may further be advantageous to prepare the activated ester or amide in the presence of a base, for example a tertiary amine. The activated ester or amide is either in situ or subsequently reacted with the amine of formula III or IV to afford the amide of formula I. The reaction normally takes place in anhydrous inert solvents, such as chlorinated hydrocarbons, e.g. dichloromethane or dichloroethane, ethers, e.g. tetrahydrofuran or 1 ,4-dioxane or carboxamides, e.g. Ν,Ν-dimethylformamide, N,N- dimethylacetamide or N-methylpyrrolidone. The reaction is ordinarily carried out at temperatures in the range from -20°C to +25°C. Scheme 5:
Figure imgf000072_0001
Scheme 6:
Figure imgf000072_0002
Scheme 7:
Figure imgf000072_0003
Scheme 8:
Figure imgf000072_0004
The 5-amino-1 -R-tetrazoles of formula III, where R6 is, for example, hydrogen or an alkyl, are either commercially available or are obtainable according to methods known from the literature. For example, 5-amino-1 -R-tetrazole can be prepared from 5-aminotetrazole according to the method described in the Journal of the American Chemical Society, 1954, 76, 923-924 (Scheme 9).
Scheme 9:
Figure imgf000072_0005
(III) Alternatively, 5-amino-1 -R-tetrazole compounds of formula III can be prepared according to the method described in the Journal of the American Chemical Society, 1954, 76, 88-89 (Scheme 10).
Scheme 10:
Figure imgf000073_0001
As shown in Scheme 1 1 , 5-amino-1 -R-triazoles of formula IV are either commercially available or are obtainable according to methods described in the literature. For example, 5- amino-1 -R-triazole can be prepared from 5-aminotriazole according to the method described Zeitschrift fur Chemie, 1990, 30, 12, 436-437.
Scheme 1 1 :
Figure imgf000073_0002
Alternatively, 5-amino-1 -R-triazole compounds of formula IV, can also be prepared analogous to the synthesis described in Chemische Berichte, 1964, 97, 2, 396-404, as shown in Scheme 12.
Scheme 12:
Figure imgf000073_0003
The compounds of formulae III, IV and V and the benzoic acid precursors of formulae II and V can be obtained by purchase or can be prepared by processes known in the art or disclosed in the literature, e.g. in WO 9746530, WO 9831676, WO 9831681 , WO 2002/018352, WO 2000/003988, US 2007/0191335, US 6277847.
The 4-amino-1 ,2,5-oxadiazole compounds of the formula V are either commercially avail- able or are obtainable according to methods known from the literature. For example, 3-alkyl-4- amino-1 ,2,5-oxadiazoles can be prepared from β-ketoesters pursuant to a procedure described in Russian Chemical Bulletin, Int. Ed., 54(4), 1032-1037 (2005), as depicted in Scheme 13.
Scheme 13:
Figure imgf000074_0001
(V)
As shown in Scheme 14, the compounds of the formula V, where R6 is halogen, can be prepared from commercially available 3,4-diamino-1 ,2,5-oxadiazole according to procedures described in the literature, e.g. by the Sandmeyer-type reaction disclosed in Heteroatom Chemistry, 15(3), 199-207 (2004).
Scheme 14:
'Sandmeyer' // w
Figure imgf000074_0002
(V)
As shown in Scheme 15, the compounds of the formula V, where R6 is a nucleophilic residue, can be prepared by introducing the nucleophilic residue via the substitution of a leaving group L, e.g. halogene, in the 4-position of the 1 ,2,5-oxadiazoles compounds of formula IX in accordance to precedures disclosed, for example in Journal of Chemical Research, Synopses (6), 190 (1985), in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (9), 2086-8 (1986) or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53(3), 596-614 (2004).
Scheme 15:
Figure imgf000074_0003
(IX) (V)
As a rule, the compounds of formula I including their stereoisomers, salts, and tautomers, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.
The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystalliza- tion or trituration. The compounds of formula I and their agriculturally suitable salts are useful as herbicides.
They are useful as such or as an appropriately formulated composition. The herbicidal compositions comprising the compound I, in particular the preferred aspects thereof, control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and weed grasses in crops such as wheat, rice, corn, soybeans 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 compounds of formula I, in particular the preferred aspects thereof, or compositions comprising them can additionally be employed in a further number of crop plants for eliminating unwanted 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 caro- ta, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arbo- reum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usi- tatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Mu- sa 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, Zea mays.
The term "crop plants" also includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information). Here, in general, one or more genes are integrated into the genetic material of the plant to improve the properties of the plant.
Accordingly, the term "crop plants" also includes plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxy- phenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, US 5,013,659) or imidazolinones (see, for example, US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as, for example, glypho- sate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors, such as, for example, glufosinate (see, for example, EP-A-0242236, EP-A-242246), or oxynil herbicides (see, for example, US 5,559,024).
In a preferred embodiment, the term "crop plants" refers to plants that comprise in their genomes a gene encoding a herbicide-tolerant wild-type or mutated HPPD protein. Such a gene may be an endogenous gene or a transgene, as described hereinafter.
By a "herbicide-tolerant" or "herbicide-resistant" plant, it is intended that a plant that is tolerant or resistant to at least one herbicide at a level that would normally kill, or inhibit the growth of, a normal or wild-type plant. By "herbicide-tolerant wild-type or mutated HPPD protein" or "herbicide -resistant wild-type or mutated HPPD protein", it is intended that such a HPPD protein displays higher HPPD activity, relative to the HPPD activity of a wild-type or reference HPPD protein, when in the presence of at least one herbicide that is known to interfere with HPPD activity and at a concentration or level of the herbicide that is known to inhibit the HPPD activity of the reference wild-type HPPD protein. Furthermore, the HPPD activity of such a herbicide-tolerant or herbicide-resistant HPPD protein may be referred to herein as "herbicide- tolerant" or "herbicide-resistant" HPPD activity.
The term "mutated HPPD nucleic acid" refers to an HPPD nucleic acid having a sequence that is mutated from a wild-type HPPD nucleic acid and that confers increased " HPPD-inhibiting herbicide" tolerance to a plant in which it is expressed. Furthermore, the term " mutated hy- droxyphenyl pyruvate dioxygenase (mutated HPPD)" refers to the replacement of an amino acid of the wild-type primary sequences SEQ ID NO: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67, a variant, a derivative, a homologue, an orthologue, or paralogue thereof, with another amino acid. The expression "mutated amino acid" will be used below to designate the amino acid which is replaced by another amino acid, thereby designating the site of the mutation in the primary sequence of the protein.
Several HPPDs and their primary sequences have been described in the state of the art, in particular the HPPDs of bacteria such as Pseudomonas (Ruetschi etal., Eur.J.Biochem., 205, 459-466, 1992, W096/38567), of plants such as Arabidopsis (W096/38567, Genebank
AF047834) or of carrot (W096/38567, Genebank 87257), of Coccicoides (Genebank COITRP), HPPDs of Brassica, cotton, Synechocystis, and tomato (US 7,297,541 ), of mammals such as the mouse or the pig. Furthermore, artificial HPPD sequences have been described, for example in US6,768,044; US6,268,549;
In a preferred embodiment, the nucleotide sequence of (i) comprises the sequence of
SEQ ID NO: 1 , 51 , 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21 , 23, 25, 27, 29, 31 , 33, 35, 37, 39, 41 , 43, 45, 47, 49, 52, 54, 56, 68, 69 or a variant or derivative thereof.
In a particularly preferred embodiment, the mutated HPPD nucleic acid useful for the present invention comprises a mutated nucleic acid sequence of SEQ ID NO: 1 or SEQ ID NO: 52, or a variant or derivative thereof.
Furthermore, it will be understood by the person skilled in the art that the nucleotide sequences of (i) or (ii) encompass homologues, paralogues and orthologues of SEQ ID NO: 1 , 51 , 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21 , 23, 25, 27, 29, 31 , 33, 35, 37, 39, 41 , 43, 45, 47, 49, 52, 54, 56, 68, 69, as defined hereinafter.
The term "variant" with respect to a sequence (e.g., a polypeptide or nucleic acid sequence such as - for example - a transcription regulating nucleotide sequence of the invention) is intended to mean substantially similar sequences. For nucleotide sequences comprising an open reading frame, variants include those sequences that, because of the degeneracy of the genetic code, encode the identical amino acid sequence of the native protein. Naturally occurring allelic variants such as these can be identified with the use of well-known molecular biology techniques, as, for example, with polymerase chain reaction (PCR) and hybridization tech- niques. Variant nucleotide sequences also include synthetically derived nucleotide sequences, such as those generated, for example, by using site-directed mutagenesis and for open reading frames, encode the native protein, as well as those that encode a polypeptide having amino acid substitutions relative to the native protein. Generally, nucleotide sequence variants of the invention will have at least 30, 40, 50, 60, to 70%, e.g., preferably 71 %, 72%, 73%, 74%, 75%, 76%, 77%, 78%, to 79%, generally at least 80%, e.g., 81 %-84%, at least 85%, e.g., 86%, 87%, 88%, 89%, 90%, 91 %, 92%, 93%, 94%, 95%, 96%, 97%, to 98% and 99% nucleotide " sequence identity" to the nucleotide sequence of SEQ ID NO:1 , 51 , 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21 , 23, 25, 27, 29, 31 , 33, 35, 37, 39, 41 , 43, 45, 47, 49, 52, 54, 56, 68, 69, 47, or 49. By "variant" polypeptide is intended a polypeptide derived from the protein of SEQ ID NO: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67, by deletion (so-called truncation) or addition of one or more amino acids to the N-terminal and/or C-terminal end of the native protein; deletion or addition of one or more amino acids at one or more sites in the native protein; or substitution of one or more amino acids at one or more sites in the native protein. Such variants may result from, for exam- pie, genetic polymorphism or from human manipulation. Methods for such manipulations are generally known in the art.
In a preferred embodiment, variants of the polynucleotides useful for the present invention will have at least 30, 40, 50, 60, to 70%, e.g., preferably 71 %, 72%, 73%, 74%, 75%, 76%, 77%, 78%, to 79%, generally at least 80%, e.g., 81 %-84%, at least 85%, e.g., 86%, 87%, 88%, 89%, 90%, 91 %, 92%, 93%, 94%, 95%, 96%, 97%, to 98% and 99% nucleotide " sequence identity" to the nucleotide sequence of SEQ ID NO:1 , 47, 49, or SEQ ID NO: 52.
It is recognized that the polynucleotide molecules and polypeptides of the invention encompass polynucleotide molecules and polypeptides comprising a nucleotide or an amino acid sequence that is sufficiently identical to nucleotide sequences set forth in SEQ ID NOs: 1 , 51 , 3, 4, 6, 7, 9, 10, 12, 13, 15, 16, 18, 19, 21 , 23, 25, 27, 29, 31 , 33, 35, 37, 39, 41 , 43, 45, 47, 49, 52, 54, 56, 68, 69, 47, or 49, or to the amino acid sequences set forth in SEQ ID NOs: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67, 48, or 50 . The term "sufficiently identical" is used herein to refer to a first amino acid or nucleotide sequence that contains a sufficient or minimum number of identical or equiva- lent (e.g., with a similar side chain) amino acid residues or nucleotides to a second amino acid or nucleotide sequence such that the first and second amino acid or nucleotide sequences have a common structural domain and/or common functional activity. "Sequence identity" refers to the extent to which two optimally aligned DNA or amino acid sequences are invariant throughout a window of alignment of components, e.g., nucleotides or amino acids. An "identity fraction" for aligned segments of a test sequence and a reference sequence is the number of identical components that are shared by the two aligned sequences divided by the total number of components in reference sequence segment, i.e., the entire reference sequence or a smaller defined part of the reference sequence. "Percent identity" is the identity fraction times 100. Optimal alignment of sequences for aligning a comparison window are well known to those skilled in the art and may be conducted by tools such as the local homology algorithm of Smith and Waterman, the homology alignment algorithm of Needleman and Wunsch, the search for similarity method of Pearson and Lipman, and preferably by computerized implementations of these algorithms such as GAP, BESTFIT, FASTA, and TFASTA available as part of the GCG. Wisconsin Package. (Accelrys Inc. Burlington, Mass.)
The terms "polynucleotide(s)", "nucleic acid sequence(s)", "nucleotide sequence(s)", " nucleic acid(s)" , " nucleic acid molecule" are used interchangeably herein and refer to nucleotides, either ribonucleotides or deoxyribonucleotides or a combination of both, in a polymeric un- branched form of any length.
"Derivatives" of a protein encompass peptides, oligopeptides, polypeptides, proteins and enzymes having amino acid substitutions, deletions and/or insertions relative to the unmodified protein in question and having similar biological and functional activity as the unmodified protein from which they are derived.
"Homologues" of a protein encompass peptides, oligopeptides, polypeptides, proteins and enzymes having amino acid substitutions, deletions and/or insertions relative to the unmodified protein in question and having similar biological and functional activity as the unmodified protein from which they are derived.
A deletion refers to removal of one or more amino acids from a protein.
An insertion refers to one or more amino acid residues being introduced into a predetermined site in a protein. Insertions may comprise N-terminal and/or C-terminal fusions as well as intra- sequence insertions of single or multiple amino acids. Generally, insertions within the amino acid sequence will be smaller than N- or C-terminal fusions, of the order of about 1 to 10 resi- dues. Examples of N- or C-terminal fusion proteins or peptides include the binding domain or activation domain of a transcriptional activator as used in the yeast two-hybrid system, phage coat proteins, (histidine)-6-tag, glutathione S-transferase-tag, protein A, maltose-binding protein, dihydrofolate reductase, Tag* 100 epitope, c-myc epitope, FLAG®-epitope, lacZ, CMP (cal- modulin-binding peptide), HA epitope, protein C epitope and VSV epitope.
A substitution refers to replacement of amino acids of the protein with other amino acids having similar properties (such as similar hydrophobicity, hydrophilicity, antigenicity, propensity to form or break a -helical structures or β -sheet structures). Amino acid substitutions are typically of single residues, but may be clustered depending upon functional constraints placed upon the polypeptide and may range from 1 to 10 amino acids; insertions will usually be of the order of about 1 to 10 amino acid residues. The amino acid substitutions are preferably conservative amino acid substitutions. Conservative substitution tables are well known in the art (see for example Creighton (1984) Proteins. W.H. Freeman and Company (Eds). Amino acid substitutions, deletions and/or insertions may readily be made using peptide synthetic techniques well known in the art, such as solid phase peptide synthesis and the like, or by recombinant DNA manipulation. Methods for the manipulation of DNA sequences to produce substitution, insertion or deletion variants of a protein are well known in the art. For example, techniques for making substitution mutations at predetermined sites in DNA are well known to those skilled in the art and include M13 mutagenesis, T7-Gen in vitro mutagenesis (USB, Cleveland, OH), QuikChange Site Directed mutagenesis (Stratagene, San Diego, CA), PCR-mediated site-directed mutagenesis or other site-directed mutagenesis protocols.
"Derivatives" further include peptides, oligopeptides, polypeptides which may, compared to the amino acid sequence of the naturally-occurring form of the protein, such as the protein of interest, comprise substitutions of amino acids with non-naturally occurring amino acid residues, or additions of non-naturally occurring amino acid residues. "Derivatives" of a protein also encompass peptides, oligopeptides, polypeptides which comprise naturally occurring altered (glycosylated, acylated, prenylated, phosphorylated, myristoylated, sulphated etc.) or non-naturally al- tered amino acid residues compared to the amino acid sequence of a naturally-occurring form of the polypeptide. A derivative may also comprise one or more non-amino acid substituents or additions compared to the amino acid sequence from which it is derived, for example a reporter molecule or other ligand, covalently or non-covalently bound to the amino acid sequence, such as a reporter molecule which is bound to facilitate its detection, and non-naturally occurring amino acid residues relative to the amino acid sequence of a naturally-occurring protein. Furthermore, "derivatives" also include fusions of the naturally-occurring form of the protein with tagging peptides such as FLAG, HIS6 or thioredoxin (for a review of tagging peptides, see Ter- pe, Appl. Microbiol. Biotechnol. 60, 523-533, 2003).
"Orthologues" and "paralogues" encompass evolutionary concepts used to describe the ances- tral relationships of genes. Paralogues are genes within the same species that have originated through duplication of an ancestral gene; orthologues are genes from different organisms that have originated through speciation, and are also derived from a common ancestral gene.
It is well-known in the art that paralogues and orthologues may share distinct domains harboring suitable amino acid residues at given sites, such as binding pockets for particular substrates or binding motifs for interaction with other proteins.
The term "domain" refers to a set of amino acids conserved at specific positions along an alignment of sequences of evolutionarily related proteins. While amino acids at other positions can vary between homologues, amino acids that are highly conserved at specific positions indicate amino acids that are likely essential in the structure, stability or function of a protein. Iden- tified by their high degree of conservation in aligned sequences of a family of protein homologues, they can be used as identifiers to determine if any polypeptide in question belongs to a previously identified polypeptide family.
The term "motif" or "consensus sequence" refers to a short conserved region in the sequence of evolutionarily related proteins. Motifs are frequently highly conserved parts of domains, but may also include only part of the domain, or be located outside of conserved domain (if all of the amino acids of the motif fall outside of a defined domain).
Specialist databases exist for the identification of domains, for example, SMART (Schultz et al. (1998) Proc. Natl. Acad. Sci. USA 95, 5857-5864; Letunic et al. (2002) Nucleic Acids Res 30, 242-244), InterPro (Mulder et al., (2003) Nucl. Acids. Res. 31 , 315-318), Prosite (Bucher and Bairoch (1994), A generalized profile syntax for biomolecular sequences motifs and its function in automatic sequence interpretation. (In) ISMB-94; Proceedings 2nd International Conference on Intelligent Systems for Molecular Biology. Altman R., Brutlag D., Karp P., Lathrop R., Searls D., Eds., pp53-61 , AAAI Press, Menlo Park; Hulo et al., Nucl. Acids. Res. 32:D134-D137, (2004)), or Pfam (Bateman et al., Nucleic Acids Research 30(1 ): 276-280 (2002)). A set of tools for in silico analysis of protein sequences is available on the ExPASy proteomics server (Swiss Institute of Bioinformatics (Gasteiger et al., ExPASy: the proteomics server for in-depth protein knowledge and analysis, Nucleic Acids Res. 31 :3784-3788(2003)). Domains or motifs may also be identified using routine techniques, such as by sequence alignment.
Methods for the alignment of sequences for comparison are well known in the art, such methods include GAP, BESTFIT, BLAST, FASTA and TFASTA. GAP uses the algorithm of Needle- man and Wunsch ((1970) J Mol Biol 48: 443-453) to find the global (i.e. spanning the complete sequences) alignment of two sequences that maximizes the number of matches and minimizes the number of gaps. The BLAST algorithm (Altschul et al. (1990) J Mol Biol 215: 403-10) calculates percent sequence identity and performs a statistical analysis of the similarity between the two sequences. The software for performing BLAST analysis is publicly available through the National Centre for Biotechnology Information (NCBI). Homologues may readily be identified using, for example, the ClustalW multiple sequence alignment algorithm (version 1 .83), with the default pairwise alignment parameters, and a scoring method in percentage. Global percentages of similarity and identity may also be determined using one of the methods available in the MatGAT software package (Campanella et al., BMC Bioinformatics. 2003 Jul 10;4:29. MatGAT: an application that generates similarity/identity matrices using protein or DNA sequences.). Minor manual editing may be performed to optimise alignment between conserved motifs, as would be apparent to a person skilled in the art. Furthermore, instead of using full-length sequences for the identification of homologues, specific domains may also be used. The sequence identity values may be determined over the entire nucleic acid or amino acid sequence or over selected domains or conserved motif(s), using the programs mentioned above using the default parameters. For local alignments, the Smith-Waterman algorithm is particularly useful (Smith TF, Waterman MS (1981 ) J. Mol. Biol 147(1 );195-7).
By substituting one or more of the key amino acid residues, the herbicide tolerance or resistance of a plant to the herbicide as described herein could be remarkably increased as compared to the activity of the wild type HPPD enzymes with SEQ ID NO: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67. Preferred substitutions of mutated HPPD are those that increase the herbicide tolerance of the plant, but leave the biological activitiy of the dioxygenase activity substantially unaffected. It will be understood by the person skilled in the art that amino acids located in a close proximity to the positions of amino acids mentioned below may also be substituted. Thus, in another em- bodiment the mutated HPPD useful for the present invention comprises a sequence of SEQ ID NO: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67, or a variant, derivative, orthologue, paralogue or homo- logue thereof, wherein an amino acid ±3, ±2 or ±1 amino acid positions from a key amino acid is substituted by any other amino acid.
Based on techniques well-known in the art, a highly characteristic sequence pattern can be developed, by means of which further of mutated HPPD candidates with the desired activity may be searched.
Searching for further mutated HPPD candidates by applying a suitable sequence pattern would also be encompassed by the present invention. It will be understood by a skilled reader that the present sequence pattern is not limited by the exact distances between two adjacent amino acid residues of said pattern. Each of the distances between two neighbours in the above patterns may, for example, vary independently of each other by up to ±10, ± 5, ±3, ±2 or ±1 amino acid positions without substantially affecting the desired activity.
In line with said above functional and spatial analysis of individual amino acid residues based on the crystallographic data as obtained according to the present invention, unique partial amino acid sequences characteristic of potentially useful mutated HPPD candidates of the invention may be identified.
In a particularly preferred embodiment, the mutated HPPD refers to a variant or derivative of SEQ ID NO: 2 wherein the substitutions are selected from the following Table 4a.
Table 4a: (Sequence ID No: 2): single amino acid substitutions
Figure imgf000081_0001
Key amino acid position Substituents
Phe404 Leu, Pro
Lys406 Thr
Gly407 Cys, His
Phe409 lie, His
Glu41 1 Thr
Leu412 Met, Phe, Trp, Ala, Ser
Ile416 Val, Phe
Ser410 Gly
Val254 Ala
Furthermore, by substituting at least two of the key amino acid residues of SEQ ID NO: 2 with specific residues, the herbicide tolerance or resistance could be remarkably increased as compared to the activity of the wild type HPPD enzymes or HPPD enzymes in which only one amino acid residue had been substituted. Therefore, in another preferred embodiment, the variant or derivative of the mutated HPPD refers to a polypeptide of SEQ ID NO: 2, wherein two, three, four or five key amino acids are substituted by another amino acid residue. Particularly preferred double, triple, quadruple, or quintuple mutations are described in Table 4b. Table 4b: (with reference to Sequence ID No: 2): combined amino acid substitutions
Combination No Key amino acid position and and its substitutents
1 A236L, E41 1 T
2 L320H, P321A
3 L320H, P321 R
4 L320N, P321A
5 L320N, P321 R
6 L320Q, P321A
7 L320Q, P321 R
8 L320Y, P321A
9 L320Y, P321 R
10 L353M, P321 R
1 1 L353M, P321 R, A236L
12 L353M, P321 R, A236L, E41 1T
13 L353M, P321 R, E41 1 T
14 L353M, P321 R, L320H
15 L353M, P321 R, L320N
16 L353M, P321 R, L320Q
17 L353M, P321 R, L320Y
18 L353M, P321 R, V212I
19 L353M, P321 R, V212I, L334E
20 L353M, P321 R, V212L, L334E Combination No Key amino acid position and and its substitutents
21 L353M, P321 R, V212L, L334E, A236L
22 L353M, P321 R, V212L, L334E, A236L, E41 1 T
23 L353M, P321 R, V212L, L334E, E41 1 T
24 L353M, P321 R, V212L, L334E, L320H
25 L353M, P321 R, V212L, L334E, L320N
26 L353M, P321 R, V212L, L334E, L320Q
27 L353M, P321 R, V212L, L334E, L320Y
28 L353M, V212I
In a particularly preferred embodiment, the mutated HPPD enzyme comprising a polypeptide of SEQ ID NO: 2, a variant, derivative, homologue, paralogue or orthologue thereof, useful for the present invention comprises one or more of the following: the amino acid corresponding to or at position 320 is histidine, asparagine or glutamine; the amino acid position 334 is glutamic acid; the amino acid position 353 is methionine; the amino acid corresponding to or at position 321 alanine or arginine; the amino acid corresponding to or at position 212 is isoleucine.
In an especially particularly preferred embodiment, the mutated HPPD refers to a polypeptide comprising SEQ ID NO: 2, wherein the leucine corresponding to or at position 320 is substituted by a histidine, and the proline corresponding to or at position 321 is substituted by an alanine. In another especially particularly preferred embodiment, the mutated HPPD refers to a polypeptide comprising SEQ ID NO: 2, wherein Leucine corresponding to or at position 353 is substituted by a Methionine, the Proline corresponding to or at position 321 is substituted by an Arginine, and the Leucine corresponding to or at position 320 is substituted by an Asparagine. In another especially particularly preferred embodiment, the mutated HPPD refers to a polypeptide comprising SEQ ID NO: 2, wherein the Leucine corresponding to or at position 353 is substituted by a Methionine, the Proline corresponding to or at position 321 is substituted by an Arginine, and the Leucine corresponding to or at position 320 is substituted by a glutamine. In another preferred embodiment, the mutated HPPD refers to a variant or derivative of SEQ ID NO: 53 wherein the substitutions are selected from the following Table 4c.
Table 4c: (Sequence ID No: 53): single amino acid substitutions
Figure imgf000083_0001
Key amino acid position Substituents Preferred substituents
Gln293 Ala, Leu, lie, Val, His, Asn, Ser His, Asn, Ser
Ile294 Thr Thr
Arg324 Lys, Ala Lys, Ala
Met335 Ala, Trp, Phe, Leu, lie, Val, Asn, Gin, Gin, Asn, His, Tyr
His, Tyr, Ser, Thr, Cys
Pro336 Ala, Arg, Gly, Asn Ala, Gly
Ser337 Ala, Pro, Thr Pro, Thr
Pro339 Deletion Deletion
Pro340 Gly Gly
Glu363 Gin Gin
Leu368 Met, Tyr, Met
Phe381 lie, Leu, Tyr lie, Leu
Leu385 Ala, Val, Gin, Asp Val, Asp
Gly386 lie, Phe lie, Phe
Thr390 Pro Pro
Phe392 Ala, Leu, Ser Ala
Ile393 Ala, Leu, Phe, Val Leu
Phe419 Leu, Pro Leu, Pro
Lys421 Thr Thr
Gly422 His, Met, Phe, Cys His, Cys
Phe424 lie, His lie, His
Leu427 Phe, Trp, Ala, Ser, Met Phe
Ile431 Val, Phe Val, Phe
Ser425 Gly Gly
Val269 Ala Ala
In another preferred embodiment, the variant or derivative of the mutated HPPD useful for the present invention refers to a polypeptide of SEQ ID NO: 53, a homologue, orthologue, or pa- ralogue thereof, wherein two, three, four or five key amino acids are substituted by another ami- no acid residue. Particularly preferred double, triple, quadruple, or quintuple mutations are described in Table 4d.
Table 4d: (reference to Sequence ID No: 53): combined amino acid substitutions
Combination Key amino acid Substituents Preferred substiNo position tuents
1 Pro336 Ala, Arg Ala
Glu363 Gin Gin
2 Pro336 Ala, Arg Ala
Glu363 Gin Gin
Leu385 Ala, Val Val Combination Key amino acid Substituents Preferred substiNo position tuents
3 Pro336 Ala, Arg Ala
Glu363 Gin Gin
Leu385 Ala, Val Val
Ile393 Ala, Leu Leu
4 Leu385 Ala, Val Val
Ile393 Ala, Leu Leu
5 Met335 Ala, Trp, Phe, Leu, lie, Val, Asn, Gin, Gin, Asn, His, Tyr
His, Tyr, Ser, Thr, Cys
Pro336 Ala, Arg, Gly Ala, Gly
6 Met335 Ala, Trp, Phe, Leu, lie, Val, Asn, Gin, Gin, Asn, His, Tyr
His, Tyr, Ser, Thr, Cys
Pro336 Ala, Arg, Gly Ala, Gly
Glu363 Gin Gin
7 Met335 Ala, Trp, Phe, Leu, lie, Val, Asn, Gin, Gin, Asn, His,
His, Tyr, Ser, Thr, Cys Tyr, Leu
Pro336 Ala, Arg, Gly Ala, Arg, Gly
Ser337 Ala, Pro, Thr Pro, Thr
Pro339 Deletion Deletion
Pro340 Gly Gly
Furthermore, by substituting the amino acids at some positions in the HPPD polypeptide sequences of Scenedesmus obliquus, the tolerance of crop plants as described herein towards the herbicides as described herein could be remarkably increased.
Thus, in a preferred embodiment, the mutated HPPD of the present invention comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, which comprises one or more of the following:
the amino acid corresponding to or at position 30 is other than proline, the amino acid corresponding to or at position 39 is other than Phe, the amino acid corresponding to or at position 54 is other than Gly, the amino acid corresponding to or at position 57 is other than Met, the amino acid corresponding to or at position 84 is other than Phe, the amino acid corresponding to or at position 210 is other than Val, the amino acid corresponding to or at position 212 is other than Asn, the amino acid corresponding to or at position 223 is other than Val, the amino acid corresponding to or at position 243 is other than Val, the amino acid corresponding to or at posi- tion 247 is other than Leu, the amino acid corresponding to or at position 249 is other than Ser, the amino acid corresponding to or at position 251 is other than Val, the amino acid corresponding to or at position 264 is other than Asn, the amino acid corresponding to or at position 291 is other than Leu, the amino acid corresponding to or at position 306 is other than His, the amino acid corresponding to or at position 317 is other than Gin, the amino acid corresponding to or at position 318 is other than Ala, the amino acid corresponding to or at position 319 is other than Ala, the amino acid corresponding to or at position 321 is other than Gly, the amino acid corresponding to or at position 326 is other than Lys, the amino acid corresponding to or at position 327 is other than Arg, the amino acid corresponding to or at position 331 is other than Lys, the amino acid corresponding to or at position 341 is other than Trp, the amino acid corresponding to or at position 342 is other than Ala, the amino acid corresponding to or at position 345 is other than Glu, the amino acid corresponding to or at position 350 is other than Leu, the amino acid corresponding to or at position 363 is other than Phe, the amino acid corresponding to or at position 367 is other than Leu, the amino acid corresponding to or at position 373 is other than lie, the amino acid corresponding to or at position 374 is other than Phe, the amino acid corre- sponding to or at position 375 is other than lie, the amino acid corresponding to or at position 379 is other than Glu, the amino acid corresponding to or at position 405 is other than Gly, the amino acid corresponding to or at position 407 is other than Phe, the amino acid corresponding to or at position 410 is other than Gly, the amino acid corresponding to or at position 412 is other than Phe, the amino acid corresponding to or at position 414 is other than Glu, the amino acid corresponding to or at position 419 is other than lie, the amino acid corresponding to or at position 421 is other than Glu, the amino acid corresponding to or at position 422 is other than Tyr.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 367 is Val, and the amino acid corresponding to or at position 375 is Leu.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of
SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 367 is Val, and the amino acid corresponding to or at position 375 is Leu, and the amino acid corresponding to or at position 39 is Leu.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 367 is Val, and the amino acid corresponding to or at position 375 is Leu, and the amino acid corresponding to or at position 39 is Trp.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 345 is Ala, Arg, Asn, Asp, Cys, Gin, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Gin
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 345 is Gin, and the amino acid corresponding to or at position 341 is lie.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 345 is Gin, and the amino acid corresponding to or at position 326 is Glu. In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 345 is Gin, and the amino acid corresponding to or at position 326 is Asp.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 345 is Gin, and the amino acid corresponding to or at position 326 is Gin.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 318 is Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Pro.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 319 is Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, Val, particularly preferred Pro.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 318 is Pro, and the amino acid corresponding to or at position 319 is Pro.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 321 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 350 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Met.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 405 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 251 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr, particularly preferred Ala.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 317 is Ala, Arg, Asn, Asp, Cys, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred His or Met.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which: the amino acid corresponding to or at position 379 is Ala, Arg, Asn, Asp, Cys, Gin, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Gin.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 350 is Met, and the amino acid corresponding to or at position 318 is Arg.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of
SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 350 is Met, and the amino acid corresponding to or at position 318 is Gly.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 350 is Met, and the amino acid corresponding to or at position 318 is Arg, and the amino acid corresponding to or at position 317 is Asn.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 210 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 317 is His, and the amino acid corresponding to or at position 318 is Gly, and the amino acid corresponding to or at position 345 is Gin.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 317 is Met, and the amino acid corresponding to or at position 318 is Gly, and the amino acid corresponding to or at position 345 is Gin.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 363 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred lie.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 419 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 249 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 247 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val. In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 407 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 306 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Lys.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 30 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 54 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of
SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 57 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 84 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 212 is Ala, Arg, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 223 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 243 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Tyr.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 264 is Ala, Arg, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which: the amino acid corresponding to or at position 291 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 327 is Ala, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of
SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 331 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 342 is Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 373 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 374 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 410 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of
SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 412 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 414 is Ala, Arg, Asn, Asp, Cys, Gin, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 421 is Ala, Arg, Asn, Asp, Cys, Gin, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 422 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, or Val. In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 251 is Ala, and the amino acid corresponding to or at position 405 is Asp.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 327 is Gly, and the amino acid corresponding to or at position 421 is Asp.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 251 is Ala, and the amino acid corresponding to or at position 306 is Arg, and the amino acid corresponding to or at position 317 is Leu, and the amino acid corresponding to or at position 318 is Pro, and the amino acid corresponding to or at position 321 is Pro, and the amino acid corresponding to or at position 331 is Glu, and the ami- no acid corresponding to or at position 350 is Met.
In another preferred embodiment, the mutated HPPD comprises a variant of the sequence of SEQ ID NO: 50, or a homologue or functional equivalent thereof, in which:
the amino acid corresponding to or at position 407 is Ala, Arg, Asn, Asp, Cys, Gin, Glu, Gly, His, lie, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.
It will be within the knowledge of the skilled artisan to identify conserved regions and motifs shared between the homologues, orthologues and paralogues of of SEQ ID NO: 2, 5, 8, 1 1 , 14, 17, 20, 22, 24, 26, 28, 30, 32, 34, 36, 38, 40, 42, 44, 46, 48, 50, 53, 55, 57, 58, 59, 60, 61 , 62, 63, 64, 65, 66, 67, and respectively SEQ ID NO: 48 or 50. Having identified such conserved regions that may represent suitable binding motifs, amino acids corresponding to the amino acids listed in Table 4a and 4b, 4c, and 4d can be chosen to be substituted by any other amino acid by conserved amino acids, and more preferably by the amino acids of tables 4a and 4b, 4c, and 4d.
Numerous crop plants, for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (mutagenesis). Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady® (glypho- sate) and Liberty Link® (glufosinate) have been generated with the aid of genetic engineering methods.
Accordingly, the term "crop plants" also includes plants which, with the aid of genetic engineering, produce one or more toxins, for example those of the bacterial strain Bacillus ssp. Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B. thuringiensis, such as the endotoxins CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 , Cry9c, Cry34Ab1 or Cry35Ab1 ; or vegetative insec- ticidal proteins (VIPs), for example VIP1 , VIP2, VIP3, or VIP3A; insecticidal proteins of nema- tode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp.; toxins of animal organisms, for example wasp, spider or scorpion toxins; fungal toxins, for example from Strep- tomycetes; plant lectins, for example from peas or barley; agglutinins; proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribo- some-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin; steroid-metabolizing enzymes, for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blockers, for example inhibitors of sodium channels or calcium channels; juvenile hormone esterase; receptors of the diuretic hormone (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the plants, these toxins may also be produced as pre- toxins, hybrid proteins or truncated or otherwise modified proteins. Hybrid proteins are charac- terized by a novel combination of different protein domains (see, for example, WO
2002/015701 ). Further examples of such toxins or genetically modified plants which produce these toxins are disclosed in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP- A 451 878, WO 03/018810 and WO 03/052073. The methods for producing these genetically modified plants are known to the person skilled in the art and disclosed, for example, in the pub- lications mentioned above. Numerous of the toxins mentioned above bestow, upon the plants by which they are produced, tolerance to pests from all taxonomic classes of arthropods, in particular to beetles (Coeleropta), dipterans (Diptera) and butterflies (Lepidoptera) and to nematodes (Nematoda).
Genetically modified plants which produce one or more genes coding for insecticidal tox- ins are described, for example, in the publications mentioned above, and some of them are commercially available, such as, for example, YieldGard® (corn varieties producing the toxin CrylAb), YieldGard® Plus (corn varieties which produce the toxins CrylAb and Cry3Bb1 ), Star- link® (corn varieties which produce the toxin Cry9c), Herculex® RW (corn varieties which produce the toxins Cry34Ab1 , Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton varieties which produce the toxin CrylAc), Bollgard® I (cotton varieties which produce the toxin CrylAc), Bollgard® II (cotton varieties which produce the toxins CrylAc and Cry2Ab2); VIPCOT® (cotton varieties which produce a VIP toxin); NewLeaf® (potato varieties which produce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin CrylAb and the PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn varieties which produce a modified version of the toxin Cry3A, see
WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn varieties which produce the toxin Cry3Bb1 ), IPC 531 from Monsanto Europe S.A., Belgium (cotton varieties which produce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1 F and the PAT enzyme).
Accordingly, the term "crop plants" also includes plants which, with the aid of genetic engineering, produce one or more proteins which are more robust or have increased resistance to bacterial, viral or fungal pathogens, such as, for example, pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora). Accordingly, the term "crop plants" also includes plants whose productivity has been improved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.
The term "crop plants" also includes plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for example by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsatu- rated omega 9 fatty acids (for example Nexera® oilseed rape).
The term "crop plants" also includes plants which have been modified with the aid of genetic engineering methods for improving the production of raw materials, for example by increasing the amylopectin content of potatoes (Amflora® potato).
Furthermore, it has been found that the compounds of formula I 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, there have been found compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of formula I.
As desiccants, the compounds of 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 pomaceous 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 readily controllable 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 compounds of formula I, or the herbicidal compositions comprising the compounds of formula I, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed. The use forms depend on the intended purpose; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.
The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.
Examples of auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.
Examples of thickeners (i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion) are
polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).
Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
Bactericides can be added for stabilizing the aqueous herbicidal formulation. Examples of bactericides are bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).
Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
Examples of colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 1 12 and C.I. Solvent Red 1 , and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
Suitable inert auxiliaries are, for example, the following:
mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.
Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and also emulsifiers) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and proteins, denatured proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.
Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of formula I or la, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
The concentrations of the compounds of formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
The formulations or ready-to-use preparations may also comprise acids, bases or buffer systems, suitable examples being phosphoric acid or sulfuric acid, or urea or ammonia.
The compounds of formula I of the invention can for example be formulated as follows: 1 . Products for dilution with water
A. Water-soluble concentrates
10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.
B. Dispersible concentrates 20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexa- none with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active compound content is 20% by weight.
C. Emulsifiable concentrates
15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has an active compound content of 15% by weight.
D. Emulsions
25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight.
E. Suspensions
In an agitated ball mill, 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable sus- pension of the active compound. The active compound content in the formulation is 20% by weight.
F. Water-dispersible granules and water-soluble granules
50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. The formulation has an active compound content of 50% by weight.
G. Water-dispersible powders and water-soluble powders
75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight.
H. Gel formulations
In a ball mill, 20 parts by weight of active compound, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or of an organic solvent are ground to give a fine suspension. Dilution with water gives a stable suspension with active compound content of 20% by weight.
2. Products to be applied undiluted
I. Dusts
5 parts by weight of active compound are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dusting powder with an active compound content of 5% by weight. J. Granules (GR, FG, GG, MG)
0.5 parts by weight of active compound are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.
K. ULV solutions (UL)
10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted with an active compound content of 10% by weight.
The compounds of formula I or the herbicidal compositions comprising them can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the herbicidal compositions or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
In a further embodiment, the compounds of formula I or the herbicidal compositions can be applied by treating seed.
The treatment of seed 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 compounds of 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, cuttings 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.
The rates of application of active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage. To treat the seed, the compounds of formula I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
It may also be advantageous to use the compounds of formula I in combination with saf- eners. Safeners are chemical compounds which prevent or reduce damage to useful plants without substantially affecting the herbicidal action of the compounds of formula I on unwanted plants. They can be used both before sowing (for example in the treatment of seed, or on cuttings or seedlings) and before or after the emergence of the useful plant. The safeners and the compounds of formula I can be used simultaneously or in succession. Suitable safeners are, for example, (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H- 1 ,2,4-triazole-3-carboxylic acids, 1 -phenyl-4,5-dihydro-5-alkyl-1 A pyrazole-S^-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha- oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-
(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5- thiazolecarboxylic acids, phosphorothiolates and O-phenyl N-alkylcarbamates and their agriculturally useful salts and, provided that they have an acid function, their agriculturally useful derivatives, such as amides, esters and thioesters.
To broaden the activity spectrum and to obtain synergistic effects, the compounds of the formula I can be mixed and jointly applied with numerous representatives of other herbicidal or growth-regulating groups of active compounds or with safeners. Suitable mixing partners are, for example, 1 ,2,4-thiadiazoles, 1 ,3,4-thiadiazoles, amides, aminophosphoric acid and its deriv- atives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1 ,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivates, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofu- ran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6- tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypro- pionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uracils and also phenylpyrazolines and isoxazolines and their derivatives.
Moreover, it may be useful to apply the compounds of formula I alone or in combination with other herbicides or else also mixed with further crop protection agents, jointly, for example with compositions for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for alleviating nutritional and trace element deficiencies. Other additives such as nonphytotoxic oils and oil concentrates may also be added. Examples of herbicides which can be used in combination with the benzamide compounds of formula I according to the present invention are:
b1 ) from the group of the lipid biosynthesis inhibitors:
alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cy- cloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, halox- yfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
b2) from the group of the ALS inhibitors:
amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac- sodium, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam, cloransulam- methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, ima- zethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac, pyrimi- nobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfome- turon-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfu- ron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfu- ron-methyl and tritosulfuron;
b3) from the group of the photosynthesis inhibitors:
ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenox- im, bromoxynil and its salts and esters, chlorobromuron, chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquat- dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, me- toxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquat- dimetilsulfate, pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, pro- panil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, ter- bumeton, terbuthylazine, terbutryn, thidiazuron and trietazine;
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, bu- tafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraf I uf en-ethyl, saflufenacil, sulfen- trazone, thidiazimin, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2 75- pyrimidinyl]-4-fluoro-N-[(isopropyl)methylsulfamoyl]benzamide (H-1 ; CAS 372137-35-4), ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3- yl)phenoxy]-2-pyridyloxy]acetate (H-2; CAS 353292-31 -6), N-ethyl-3-(2,6-dichloro-4-trifluoro- methylphenoxy)-5-methyl-1 pyrazole-1 -carboxamide (H-3; CAS 452098-92-9),
N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 A pyrazole-l - carboxamide (H-4; CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5- methyl-1 pyrazole-1 -carboxamide (H-5; CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6- fluoro-4-trifluoromethylphenoxy)-5-methyl-1 pyrazole-1 -carboxamide (H-6; CAS 45100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo- [1 ,3,5]triazinan-2,4-dione, 1 ,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4- dihydro-2H-benzo[b][1 ,4]oxazin-6-yl)-1 ,3,5-triazinane-2,4-dione, 2-(2,2,7-Trifluoro-3-oxo-4-prop- 2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione and 1 - Methyl-6-trifluoromethyl-3-(2,27-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin 6-yl)-1 H-pyrimidine-2,4-dione;
b5) from the group of the bleacher herbicides:
aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone, diflufenican, flu- ridone, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfu- tole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 4-hydroxy- 3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2- one (H-7; CAS 352010-68-5) and 4-(3-trifluoromethylphenoxy)-2-(4- trifluoromethylphenyl)pyrimidine (H-8; CAS 180608-33-7);
b6) from the group of the EPSP synthase inhibitors:
glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors:
bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;
b8) from the group of the DHP synthase inhibitors:
asulam;
b9) from the group of the mitose inhibitors:
amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin, carbetamide, chlor- propham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;
b10) from the group of the VLCFA inhibitors:
acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethanamid, dime- thenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchlor;
Compounds of the formula 2:
Figure imgf000100_0001
in which the variables have the following meanings:
Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset, which radicals may be substituted by one to three groups Raa; R21,R22,R23,R24 are H, halogen or Ci-C4-alkyl; X is O or NH; n is 0 or 1 .
Compounds of the formula 2 have in particular the following meanings:
Figure imgf000101_0001
where # denotes the bond to the skeleton of the molecule; and
R2i i R22 R23 R24 ARE Η Ι C! I F OR CH3; R25 js halogen, Ci-C4-alkyl or Ci-C4-haloalkyl; R26 is C1-C4- alkyl; R27 is halogen, Ci-C4-alkoxy or Ci-C4-haloalkoxy; R28 is H, halogen, Ci-C4-alkyl, Ci-C4- haloalkyl or Ci-C4-haloalkoxy; m is 0, 1 , 2 or 3; X is oxygen; n is 0 or 1 .
Preferred compounds of the formula 2 have the following meanings:
Figure imgf000101_0002
R21 is H; R22,R23 are F; R24 is H or F; X is oxygen; N is 0 or 1 .
Particularly preferred compounds of the formula 2 are:
3-[5-(2,2-difluoroethoxy)-1 -methyl-3-trifluoromethyl-1 H-pyrazol-4-ylmethane- sulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-1 ); 3-{[5-(2,2-difluoroethoxy)-1 -methyl-3- trifluoromethyl-1 H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-2); 4-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H- [1 ,2,3]triazole (2-3); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5- trifluoromethyl-2H-[1 ,2,3]triazole (2-4); 4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2- methyl-5-trifluoromethyl-2H-[1 ,2,3]triazole (2-5); 3-{[5-(2,2-difluoroethoxy)-1 -methyl-3- trifluoromethyl-1 H-pyrazol-4-yl]difluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-6); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoromethyl-2H- [1 ,2,3]triazole (2-7); 3-{[5-(2,2-difluoroethoxy)-1 -methyl-3-trifluoromethyl-1 H-pyrazol-4- yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-8); 4-[difluoro-(4- fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluoromethyl-2H- [1 ,2,3]triazole (2-9);
b1 1 ) from the group of the cellulose biosynthesis inhibitors:
chlorthiamid, dichlobenil, flupoxam and isoxaben;
b12) from the group of the decoupler herbicides:
dinoseb, dinoterb and DNOC and its salts;
b13) from the group of the auxin herbicides:
2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts such as aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA and its salts and esters, MCPA- thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4- pyrimidinecarboxylic acid (H-9; CAS 858956-08-8) and its salts and esters; b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;
b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol- methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dime- thipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flam- prop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fos- amine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6- methylphenoxy)-4-pyridazinol (H-10; CAS 499223-49-3) and its salts and esters.
Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfa- mide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furi- lazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1 - oxa-4-azaspiro[4.5]decane (H-1 1 ; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl)-1 ,3-oxazolidine (H-12; R-29148, CAS 52836-31 -4).
The active compounds of groups b1 ) to b15) and the safeners C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names
(http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, R. R. Schmidt, Herbizide
[Herbicides], Georg Thieme Verlag, Stuttgart, 1995. Further herbicidally active compounds are known from WO 96/26202, WO 97/41 1 16, WO 97/41 1 17, WO 97/41 1 18, WO 01/83459 and WO 2008/074991 and from W. Kramer et al. (ed.) "Modern Crop Protection Compounds", Vol. 1 , Wiley VCH, 2007 and the literature quoted therein.
The invention also relates to compositions in the form of a crop protection composition formulated as a 1 -component composition comprising an active compound combination com- prising at least one benzamide compound of the formula I and at least one further active compound, preferably selected from the active compounds of groups b1 to b15, and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.
The invention also relates to compositions in the form of a crop protection composition formulat- ed as a 2-component composition comprising a first component comprising at least one compound of the formula I, a solid or liquid carrier and/or one or more surfactants and a second component comprising at least one further active compound selected from the active compounds of groups b1 to b15, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for crop protection compositions.
In binary compositions comprising at least one compound of the formula I as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1 : 1000 to 1000: 1 , preferably in the range of from 1 :500 to 500: 1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
In binary compositions comprising at least one compound of the formula I as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 .
In ternary compositions comprising both at least one compound of the formula I as component A, at least one herbicide B and at least one safener C, the relative parts by weight of the components A:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 ; the weight ratio of the components A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 ; and the weight ratio of the components B:C is generally in the range of from 1 : 1000 to 1000: 1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 . Preferably, the weight ratio of the components A + B to the component C is in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
Examples of particularly preferred compositions according to the invention comprising in each case one individualized compound of the formula I and one mixing partner or a mixing partner combination are given in Table B below.
A further aspect of the invention relates to the compositions B-1 to B-1236 listed in Table B below, where in each case one row of Table B corresponds to a herbicidal composition com- prising one of the compounds of formula I individualized in the above description (component 1 ) and the further active compound from groups b1 ) to b15) and/or safener C stated in each case in the row in question (component 2). The active compounds in the compositions described are in each case preferably present in synergistically effective amounts.
Table B:
Figure imgf000103_0001
Herbicide(s) B Safener C
B-16 flumetsulam —
B-17 flupyrsulfuron-methyl-sodium —
B-18 foramsulfuron —
B-19 imazamox —
B-20 imazapic —
B-21 imazapyr —
B-22 imazaquin —
B-23 imazethapyr —
B-24 imazosulfuron —
B-25 iodosulfuron-methyl-sodium —
B-26 mesosulfuron —
B-27 nicosulfuron —
B-28 penoxsulam —
B-29 propoxycarbazone-sodium —
B-30 pyrazosulfuron-ethyl —
B-31 pyroxsulam —
B-32 rimsulfuron —
B-33 sulfosulfuron —
B-34 thiencarbazone-methyl —
B-35 tritosulfuron —
B-36 2,4-D and its salts and esters —
B-37 aminopyralid and its salts and esters —
B-38 clopyralid and its salts and esters —
B-39 dicamba and its salts and esters —
B-40 fluroxypyr-meptyl —
B-41 quinclorac —
B-42 quinmerac —
B-43 H-9 —
B-44 diflufenzopyr —
B-45 diflufenzopyr-sodium —
B-46 clomazone —
B-47 diflufenican —
B-48 fluorochloridone —
B-49 isoxaflutol —
B-50 mesotrione —
B-51 picolinafen —
B-52 sulcotrione —
B-53 tefuryltrione —
B-54 tembotrione —
B-55 topramezone — Herbicide(s) B Safener C
B-56 H-7 —
B-57 atrazine —
B-58 diuron —
B-59 fluometuron —
B-60 hexazinone —
B-61 isoproturon —
B-62 metribuzin —
B-63 propanil —
B-64 terbuthylazine —
B-65 paraquat dichloride —
B-66 flumioxazin —
B-67 oxyfluorfen —
B-68 saflufenacil —
B-69 sulfentrazone —
B-70 H-1 —
B-71 H-2 —
B-72 glyphosate —
B-73 glyphosate-isopropylammonium —
B-74 glyphosate-trimesium (sulfosate) —
B-75 glufosinate —
B-76 glufosinate-ammonium —
B-77 pendimethalin —
B-78 trifluralin —
B-79 acetochlor —
B-80 cafenstrole —
B-81 dimethenamid-P —
B-82 fentrazamide —
B-83 flufenacet —
B-84 mefenacet —
B-85 metazachlor —
B-86 metolachlor-S —
B-87 pyroxasulfone —
B-88 isoxaben —
B-89 dymron —
B-90 indanofan —
B-91 oxaziclomefone —
B-92 triaziflam —
B-93 chlorotoluron —
B-94 atrazine + H-1 —
B-95 atrazine + glyphosate — Herbicide(s) B Safener C
B-96 atrazine + mesotrione —
B-97 atrazine + nicosulfuron —
B-98 atrazine + tembotrione —
B-99 atrazine + topramezone —
B-100 clomazone + glyphosate —
B-101 diflufenican + clodinafop-propargyl —
B-102 diflufenican + fenoxaprop-P-ethyl —
B-103 diflufenican + flupyrsulfuron-methyl-sodium —
B-104 diflufenican + glyphosate —
B-105 diflufenican + mesosulfuron-methyl —
B-106 diflufenican + pinoxaden —
B-107 diflufenican + pyroxsulam —
B-108 flumetsulam + glyphosate —
B-109 flumioxazin + glyphosate —
B-1 10 imazapic + glyphosate —
B-1 1 1 imazethapyr + glyphosate —
B-1 12 isoxaflutol + H-1 —
B-1 13 isoxaflutol + glyphosate —
B-1 14 metazachlor + H-1 —
B-1 15 metazachlor + glyphosate —
B-1 16 metazachlor + mesotrione —
B-1 17 metazachlor + nicosulfuron —
B-1 18 metazachlor + terbuthylazine —
B-1 19 metazachlor + topramezone —
B-120 metribuzin + glyphosate —
B-121 pendimethalin + H-1 —
B-122 pendimethalin + clodinafop-propargyl —
B-123 pendimethalin + fenoxaprop-P-ethyl —
B-124 pendimethalin + flupyrsulfuron-methyl-sodium —
B-125 pendimethalin + glyphosate —
B-126 pendimethalin + mesosulfuron-methyl —
B-127 pendimethalin + mesotrione —
B-128 pendimethalin + nicosulfuron —
B-129 pendimethalin + pinoxaden —
B-130 pendimethalin + pyroxsulam —
B-131 pendimethalin + tembotrione —
B-132 pendimethalin + topramezone —
B-133 pyroxasulfone + tembotrione —
B-134 pyroxasulfone + topramezone —
B-135 sulfentrazone + glyphosate — Herbicide(s) B Safener C
B-136 terbuthylazine + H-1 —
B-137 terbuthylazine + foramsulfuron —
B-138 terbuthylazine + glyphosate —
B-139 terbuthylazine + mesotrione —
B-140 terbuthylazine + nicosulfuron —
B-141 terbuthylazine + tembotrione —
B-142 terbuthylazine + topramezone —
B-143 trifluralin + glyphosate —
B-144 — benoxacor
B-145 — cloquintocet
B-146 — cyprosulfamide
B-147 — dichlormid
B-148 — fenchlorazole
B-149 — isoxadifen
B-150 — mefenpyr
B-151 — H-1 1
B-152 — H-12
B-153 clodinafop-propargyl benoxacor
B-154 cycloxydim benoxacor
B-155 cyhalofop-butyl benoxacor
B-156 fenoxaprop-P-ethyl benoxacor
B-157 pinoxaden benoxacor
B-158 profoxydim benoxacor
B-159 tepraloxydim benoxacor
B-160 tralkoxydim benoxacor
B-161 esprocarb benoxacor
B-162 prosulfocarb benoxacor
B-163 thiobencarb benoxacor
B-164 triallate benoxacor
B-165 bensulfuron-methyl benoxacor
B-166 bispyribac-sodium benoxacor
B-167 cyclosulfamuron benoxacor
B-168 flumetsulam benoxacor
B-169 flupyrsulfuron-methyl-sodium benoxacor
B-170 foramsulfuron benoxacor
B-171 imazamox benoxacor
B-172 imazapic benoxacor
B-173 imazapyr benoxacor
B-174 imazaquin benoxacor
B-175 imazethapyr benoxacor Herbicide(s) B Safener C
B-176 imazosulfuron benoxacor
B-177 iodosulfuron-methyl-sodium benoxacor
B-178 mesosulfuron benoxacor
B-179 nicosulfuron benoxacor
B-180 penoxsulam benoxacor
B-181 propoxycarbazone-sodium benoxacor
B-182 pyrazosulfuron-ethyl benoxacor
B-183 pyroxsulam benoxacor
B-184 rimsulfuron benoxacor
B-185 sulfosulfuron benoxacor
B-186 thiencarbazone-methyl benoxacor
B-187 tritosulfuron benoxacor
B-188 2,4-D and its salts and esters benoxacor
B-189 aminopyralid and its salts and esters benoxacor
B-190 clopyralid and its salts and esters benoxacor
B-191 dicamba and its salts and esters benoxacor
B-192 fluroxypyr-meptyl benoxacor
B-193 quinclorac benoxacor
B-194 quinmerac benoxacor
B-195 H-9 benoxacor
B-196 diflufenzopyr benoxacor
B-197 diflufenzopyr-sodium benoxacor
B-198 clomazone benoxacor
B-199 diflufenican benoxacor
B-200 fluorochloridone benoxacor
B-201 isoxaflutol benoxacor
B-202 mesotrione benoxacor
B-203 picolinafen benoxacor
B-204 sulcotrione benoxacor
B-205 tefuryltrione benoxacor
B-206 tembotrione benoxacor
B-207 topramezone benoxacor
B-208 H-7 benoxacor
B-209 atrazine benoxacor
B-210 diuron benoxacor
B-21 1 fluometuron benoxacor
B-212 hexazinone benoxacor
B-213 isoproturon benoxacor
B-214 metribuzin benoxacor
B-215 propanil benoxacor Herbicide(s) B Safener C
B-216 terbuthylazine benoxacor
B-217 paraquat dichloride benoxacor
B-218 flumioxazin benoxacor
B-219 oxyfluorfen benoxacor
B-220 saflufenacil benoxacor
B-221 sulfentrazone benoxacor
B-222 H-1 benoxacor
B-223 H-2 benoxacor
B-224 glyphosate benoxacor
B-225 glyphosate-isopropylammonium benoxacor
B-226 glyphosate-trimesium (sulfosate) benoxacor
B-227 glufosinate benoxacor
B-228 glufosinate-ammonium benoxacor
B-229 pendimethalin benoxacor
B-230 trifluralin benoxacor
B-231 acetochlor benoxacor
B-232 cafenstrole benoxacor
B-233 dimethenamid-P benoxacor
B-234 fentrazamide benoxacor
B-235 flufenacet benoxacor
B-236 mefenacet benoxacor
B-237 metazachlor benoxacor
B-238 metolachlor-S benoxacor
B-239 pyroxasulfone benoxacor
B-240 isoxaben benoxacor
B-241 dymron benoxacor
B-242 indanofan benoxacor
B-243 oxaziclomefone benoxacor
B-244 triaziflam benoxacor
B-245 atrazine + H-1 benoxacor
B-246 atrazine + glyphosate benoxacor
B-247 atrazine + mesotrione benoxacor
B-248 atrazine + nicosulfuron benoxacor
B-249 atrazine + tembotrione benoxacor
B-250 atrazine + topramezone benoxacor
B-251 clomazone + glyphosate benoxacor
B-252 diflufenican + clodinafop-propargyl benoxacor
B-253 diflufenican + fenoxaprop-P-ethyl benoxacor
B-254 diflufenican + flupyrsulfuron-methyl-sodium benoxacor
B-255 diflufenican + glyphosate benoxacor Herbicide(s) B Safener C
B-256 diflufenican + mesosulfuron-methyl benoxacor
B-257 diflufenican + pinoxaden benoxacor
B-258 diflufenican + pyroxsulam benoxacor
B-259 flumetsulam + glyphosate benoxacor
B-260 flumioxazin + glyphosate benoxacor
B-261 imazapic + glyphosate benoxacor
B-262 imazethapyr + glyphosate benoxacor
B-263 isoxaflutol + H-1 benoxacor
B-264 isoxaflutol + glyphosate benoxacor
B-265 metazachlor + H-1 benoxacor
B-266 metazachlor + glyphosate benoxacor
B-267 metazachlor + mesotrione benoxacor
B-268 metazachlor + nicosulfuron benoxacor
B-269 metazachlor + terbuthylazine benoxacor
B-270 metazachlor + topramezone benoxacor
B-271 metribuzin + glyphosate benoxacor
B-272 pendimethalin + H-1 benoxacor
B-273 pendimethalin + clodinafop-propargyl benoxacor
B-274 pendimethalin + fenoxaprop-P-ethyl benoxacor
B-275 pendimethalin + flupyrsulfuron-methyl-sodium benoxacor
B-276 pendimethalin + glyphosate benoxacor
B-277 pendimethalin + mesosulfuron-methyl benoxacor
B-278 pendimethalin + mesotrione benoxacor
B-279 pendimethalin + nicosulfuron benoxacor
B-280 pendimethalin + pinoxaden benoxacor
B-281 pendimethalin + pyroxsulam benoxacor
B-282 pendimethalin + tembotrione benoxacor
B-283 pendimethalin + topramezone benoxacor
B-284 pyroxasulfone + tembotrione benoxacor
B-285 pyroxasulfone + topramezone benoxacor
B-286 sulfentrazone + glyphosate benoxacor
B-287 terbuthylazine + H-1 benoxacor
B-288 terbuthylazine + foramsulfuron benoxacor
B-289 terbuthylazine + glyphosate benoxacor
B-290 terbuthylazine + mesotrione benoxacor
B-291 terbuthylazine + nicosulfuron benoxacor
B-292 terbuthylazine + tembotrione benoxacor
B-293 terbuthylazine + topramezone benoxacor
B-294 trifluralin + glyphosate benoxacor
B-295 clodinafop-propargyl cloquintocet Herbicide(s) B Safener C
B-296 cycloxydim cloquintocet
B-297 cyhalofop-butyl cloquintocet
B-298 fenoxaprop-P-ethyl cloquintocet
B-299 pinoxaden cloquintocet
B-300 profoxydim cloquintocet
B-301 tepraloxydim cloquintocet
B-302 tralkoxydim cloquintocet
B-303 esprocarb cloquintocet
B-304 prosulfocarb cloquintocet
B-305 thiobencarb cloquintocet
B-306 triallate cloquintocet
B-307 bensulfuron-methyl cloquintocet
B-308 bispyribac-sodium cloquintocet
B-309 cyclosulfamuron cloquintocet
B-310 flumetsulam cloquintocet
B-31 1 flupyrsulfuron-methyl-sodium cloquintocet
B-312 foramsulfuron cloquintocet
B-313 imazamox cloquintocet
B-314 imazapic cloquintocet
B-315 imazapyr cloquintocet
B-316 imazaquin cloquintocet
B-317 imazethapyr cloquintocet
B-318 imazosulfuron cloquintocet
B-319 iodosulfuron-methyl-sodium cloquintocet
B-320 mesosulfuron cloquintocet
B-321 nicosulfuron cloquintocet
B-322 penoxsulam cloquintocet
B-323 propoxycarbazone-sodium cloquintocet
B-324 pyrazosulfuron-ethyl cloquintocet
B-325 pyroxsulam cloquintocet
B-326 rimsulfuron cloquintocet
B-327 sulfosulfuron cloquintocet
B-328 thiencarbazone-methyl cloquintocet
B-329 tritosulfuron cloquintocet
B-330 2,4-D and its salts and esters cloquintocet
B-331 aminopyralid and its salts and esters cloquintocet
B-332 clopyralid and its salts and esters cloquintocet
B-333 dicamba and its salts and esters cloquintocet
B-334 fluroxypyr-meptyl cloquintocet
B-335 quinclorac cloquintocet Herbicide(s) B Safener C
B-336 quinmerac cloquintocet
B-337 H-9 cloquintocet
B-338 diflufenzopyr cloquintocet
B-339 diflufenzopyr-sodium cloquintocet
B-340 clomazone cloquintocet
B-341 diflufenican cloquintocet
B-342 fluorochloridone cloquintocet
B-343 isoxaflutol cloquintocet
B-344 mesotrione cloquintocet
B-345 picolinafen cloquintocet
B-346 sulcotrione cloquintocet
B-347 tefuryltrione cloquintocet
B-348 tembotrione cloquintocet
B-349 topramezone cloquintocet
B-350 H-7 cloquintocet
B-351 atrazine cloquintocet
B-352 diuron cloquintocet
B-353 fluometuron cloquintocet
B-354 hexazinone cloquintocet
B-355 isoproturon cloquintocet
B-356 metribuzin cloquintocet
B-357 propanil cloquintocet
B-358 terbuthylazine cloquintocet
B-359 paraquat dichloride cloquintocet
B-360 flumioxazin cloquintocet
B-361 oxyfluorfen cloquintocet
B-362 saflufenacil cloquintocet
B-363 sulfentrazone cloquintocet
B-364 H-1 cloquintocet
B-365 H-2 cloquintocet
B-366 glyphosate cloquintocet
B-367 glyphosate-isopropylammonium cloquintocet
B-368 glyphosate-trimesium (sulfosate) cloquintocet
B-369 glufosinate cloquintocet
B-370 glufosinate-ammonium cloquintocet
B-371 pendimethalin cloquintocet
B-372 trifluralin cloquintocet
B-373 acetochlor cloquintocet
B-374 cafenstrole cloquintocet
B-375 dimethenamid-P cloquintocet Herbicide(s) B Safener C
B-376 fentrazamide cloquintocet
B-377 flufenacet cloquintocet
B-378 mefenacet cloquintocet
B-379 metazachlor cloquintocet
B-380 metolachlor-S cloquintocet
B-381 pyroxasulfone cloquintocet
B-382 isoxaben cloquintocet
B-383 dymron cloquintocet
B-384 indanofan cloquintocet
B-385 oxaziclomefone cloquintocet
B-386 triaziflam cloquintocet
B-387 atrazine + H-1 cloquintocet
B-388 atrazine + glyphosate cloquintocet
B-389 atrazine + mesotrione cloquintocet
B-390 atrazine + nicosulfuron cloquintocet
B-391 atrazine + tembotrione cloquintocet
B-392 atrazine + topramezone cloquintocet
B-393 clomazone + glyphosate cloquintocet
B-394 diflufenican + clodinafop-propargyl cloquintocet
B-395 diflufenican + fenoxaprop-p-ethyl cloquintocet
B-396 diflufenican + flupyrsulfuron-methyl-sodium cloquintocet
B-397 diflufenican + glyphosate cloquintocet
B-398 diflufenican + mesosulfuron-methyl cloquintocet
B-399 diflufenican + pinoxaden cloquintocet
B-400 diflufenican + pyroxsulam cloquintocet
B-401 flumetsulam + glyphosate cloquintocet
B-402 flumioxazin + glyphosate cloquintocet
B-403 imazapic + glyphosate cloquintocet
B-404 imazethapyr + glyphosate cloquintocet
B-405 isoxaflutol + H-1 cloquintocet
B-406 isoxaflutol + glyphosate cloquintocet
B-407 metazachlor + H-1 cloquintocet
B-408 metazachlor + glyphosate cloquintocet
B-409 metazachlor + mesotrione cloquintocet
B-410 metazachlor + nicosulfuron cloquintocet
B-41 1 metazachlor + terbuthylazine cloquintocet
B-412 metazachlor + topramezone cloquintocet
B-413 metribuzin + glyphosate cloquintocet
B-414 pendimethalin + H-1 cloquintocet
B-415 pendimethalin + clodinafop-propargyl cloquintocet Herbicide(s) B Safener C
B-416 pendimethalin + fenoxaprop-P-ethyl cloquintocet
B-417 pendimethalin + flupyrsulfuron-methyl-sodium cloquintocet
B-418 pendimethalin + glyphosate cloquintocet
B-419 pendimethalin + mesosulfuron-methyl cloquintocet
B-420 pendimethalin + mesotrione cloquintocet
B-421 pendimethalin + nicosulfuron cloquintocet
B-422 pendimethalin + pinoxaden cloquintocet
B-423 pendimethalin + pyroxsulam cloquintocet
B-424 pendimethalin + tembotrione cloquintocet
B-425 pendimethalin + topramezone cloquintocet
B-426 pyroxasulfone + tembotrione cloquintocet
B-427 pyroxasulfone + topramezone cloquintocet
B-428 sulfentrazone + glyphosate cloquintocet
B-429 terbuthylazine + H-1 cloquintocet
B-430 terbuthylazine + foramsulfuron cloquintocet
B-431 terbuthylazine + glyphosate cloquintocet
B-432 terbuthylazine + mesotrione cloquintocet
B-433 terbuthylazine + nicosulfuron cloquintocet
B-434 terbuthylazine + tembotrione cloquintocet
B-435 terbuthylazine + topramezone cloquintocet
B-436 trifluralin + glyphosate cloquintocet
B-437 clodinafop-propargyl dichlormid
B-438 cycloxydim dichlormid
B-439 cyhalofop-butyl dichlormid
B-440 fenoxaprop-P-ethyl dichlormid
B-441 pinoxaden dichlormid
B-442 profoxydim dichlormid
B-443 tepraloxydim dichlormid
B-444 tralkoxydim dichlormid
B-445 esprocarb dichlormid
B-446 prosulfocarb dichlormid
B-447 thiobencarb dichlormid
B-448 triallate dichlormid
B-449 bensulfuron-methyl dichlormid
B-450 bispyribac-sodium dichlormid
B-451 cyclosulfamuron dichlormid
B-452 flumetsulam dichlormid
B-453 flupyrsulfuron-methyl-sodium dichlormid
B-454 foramsulfuron dichlormid
B-455 imazamox dichlormid Herbicide(s) B Safener C
B-456 imazapic dichlormid
B-457 imazapyr dichlormid
B-458 imazaquin dichlormid
B-459 imazethapyr dichlormid
B-460 imazosulfuron dichlormid
B-461 iodosulfuron-methyl-sodium dichlormid
B-462 mesosulfuron dichlormid
B-463 nicosulfuron dichlormid
B-464 penoxsulam dichlormid
B-465 propoxycarbazone-sodium dichlormid
B-466 pyrazosulfuron-ethyl dichlormid
B-467 pyroxsulam dichlormid
B-468 rimsulfuron dichlormid
B-469 sulfosulfuron dichlormid
B-470 thiencarbazone-methyl dichlormid
B-471 tritosulfuron dichlormid
B-472 2,4-D and its salts and esters dichlormid
B-473 aminopyralid and its salts and esters dichlormid
B-474 clopyralid and its salts and esters dichlormid
B-475 dicamba and its salts and esters dichlormid
B-476 fluroxypyr-meptyl dichlormid
B-477 quinclorac dichlormid
B-478 quinmerac dichlormid
B-479 H-9 dichlormid
B-480 diflufenzopyr dichlormid
B-481 diflufenzopyr-sodium dichlormid
B-482 clomazone dichlormid
B-483 diflufenican dichlormid
B-484 fluorochloridone dichlormid
B-485 isoxaflutol dichlormid
B-486 mesotrione dichlormid
B-487 picolinafen dichlormid
B-488 sulcotrione dichlormid
B-489 tefuryltrione dichlormid
B-490 tembotrione dichlormid
B-491 topramezone dichlormid
B-492 H-7 dichlormid
B-493 atrazine dichlormid
B-494 diuron dichlormid
B-495 fluometuron dichlormid Herbicide(s) B Safener C
B-496 hexazinone dichlormid
B-497 isoproturon dichlormid
B-498 metribuzin dichlormid
B-499 propanil dichlormid
B-500 terbuthylazine dichlormid
B-501 paraquat dichloride dichlormid
B-502 flumioxazin dichlormid
B-503 oxyfluorfen dichlormid
B-504 saflufenacil dichlormid
B-505 sulfentrazone dichlormid
B-506 H-1 dichlormid
B-507 H-2 dichlormid
B-508 glyphosate dichlormid
B-509 glyphosate-isopropylammonium dichlormid
B-510 glyphosate-trimesium (sulfosate) dichlormid
B-51 1 glufosinate dichlormid
B-512 glufosinate-ammonium dichlormid
B-513 pendimethalin dichlormid
B-514 trifluralin dichlormid
B-515 acetochlor dichlormid
B-516 cafenstrole dichlormid
B-517 dimethenamid-P dichlormid
B-518 fentrazamide dichlormid
B-519 flufenacet dichlormid
B-520 mefenacet dichlormid
B-521 metazachlor dichlormid
B-522 metolachlor-S dichlormid
B-523 pyroxasulfone dichlormid
B-524 isoxaben dichlormid
B-525 dymron dichlormid
B-526 indanofan dichlormid
B-527 oxaziclomefone dichlormid
B-528 triaziflam dichlormid
B-529 atrazine + H-1 dichlormid
B-530 atrazine + glyphosate dichlormid
B-531 atrazine + mesotrione dichlormid
B-532 atrazine + nicosulfuron dichlormid
B-533 atrazine + tembotrione dichlormid
B-534 atrazine + topramezone dichlormid
B-535 clomazone + glyphosate dichlormid Herbicide(s) B Safener C
B-536 diflufenican + clodinafop-propargyl dichlormid
B-537 diflufenican + fenoxaprop-p-ethyl dichlormid
B-538 diflufenican + flupyrsulfuron-methyl-sodium dichlormid
B-539 diflufenican + glyphosate dichlormid
B-540 diflufenican + mesosulfuron-methyl dichlormid
B-541 diflufenican + pinoxaden dichlormid
B-542 diflufenican + pyroxsulam dichlormid
B-543 flumetsulam + glyphosate dichlormid
B-544 flumioxazin + glyphosate dichlormid
B-545 imazapic + glyphosate dichlormid
B-546 imazethapyr + glyphosate dichlormid
B-547 isoxaflutol + H-1 dichlormid
B-548 isoxaflutol + glyphosate dichlormid
B-549 metazachlor + H-1 dichlormid
B-550 metazachlor + glyphosate dichlormid
B-551 metazachlor + mesotrione dichlormid
B-552 metazachlor + nicosulfuron dichlormid
B-553 metazachlor + terbuthylazine dichlormid
B-554 metazachlor + topramezone dichlormid
B-555 metribuzin + glyphosate dichlormid
B-556 pendimethalin + H-1 dichlormid
B-557 pendimethalin + clodinafop-propargyl dichlormid
B-558 pendimethalin + fenoxaprop-P-ethyl dichlormid
B-559 pendimethalin + flupyrsulfuron-methyl-sodium dichlormid
B-560 pendimethalin + glyphosate dichlormid
B-561 pendimethalin + mesosulfuron-methyl dichlormid
B-562 pendimethalin + mesotrione dichlormid
B-563 pendimethalin + nicosulfuron dichlormid
B-564 pendimethalin + pinoxaden dichlormid
B-565 pendimethalin + pyroxsulam dichlormid
B-566 pendimethalin + tembotrione dichlormid
B-567 pendimethalin + topramezone dichlormid
B-568 pyroxasulfone + tembotrione dichlormid
B-569 pyroxasulfone + topramezone dichlormid
B-570 sulfentrazone + glyphosate dichlormid
B-571 terbuthylazine + H-1 dichlormid
B-572 terbuthylazine + foramsulfuron dichlormid
B-573 terbuthylazine + glyphosate dichlormid
B-574 terbuthylazine + mesotrione dichlormid
B-575 terbuthylazine + nicosulfuron dichlormid Herbicide(s) B Safener C
B-576 terbuthylazine + tembotrione dichlormid
B-577 terbuthylazine + topramezone dichlormid
B-578 trifluralin + glyphosate dichlormid
B-579 clodinafop-propargyl fenchlorazole
B-580 cycloxydim fenchlorazole
B-581 cyhalofop-butyl fenchlorazole
B-582 fenoxaprop-P-ethyl fenchlorazole
B-583 pinoxaden fenchlorazole
B-584 profoxydim fenchlorazole
B-585 tepraloxydim fenchlorazole
B-586 tralkoxydim fenchlorazole
B-587 esprocarb fenchlorazole
B-588 prosulfocarb fenchlorazole
B-589 thiobencarb fenchlorazole
B-590 triallate fenchlorazole
B-591 bensulfuron-methyl fenchlorazole
B-592 bispyribac-sodium fenchlorazole
B-593 cyclosulfamuron fenchlorazole
B-594 flumetsulam fenchlorazole
B-595 flupyrsulfuron-methyl-sodium fenchlorazole
B-596 foramsulfuron fenchlorazole
B-597 imazamox fenchlorazole
B-598 imazapic fenchlorazole
B-599 imazapyr fenchlorazole
B-600 imazaquin fenchlorazole
B-601 imazethapyr fenchlorazole
B-602 imazosulfuron fenchlorazole
B-603 iodosulfuron-methyl-sodium fenchlorazole
B-604 mesosulfuron fenchlorazole
B-605 nicosulfuron fenchlorazole
B-606 penoxsulam fenchlorazole
B-607 propoxycarbazone-sodium fenchlorazole
B-608 pyrazosulfuron-ethyl fenchlorazole
B-609 pyroxsulam fenchlorazole
B-610 rimsulfuron fenchlorazole
B-61 1 sulfosulfuron fenchlorazole
B-612 thiencarbazone-methyl fenchlorazole
B-613 tritosulfuron fenchlorazole
B-614 2,4-D and its salts and esters fenchlorazole
B-615 aminopyralid and its salts and esters fenchlorazole Herbicide(s) B Safener C
B-616 clopyralid and its salts and esters fenchlorazole
B-617 dicamba and its salts and esters fenchlorazole
B-618 fluroxypyr-meptyl fenchlorazole
B-619 quinclorac fenchlorazole
B-620 quinmerac fenchlorazole
B-621 H-9 fenchlorazole
B-622 diflufenzopyr fenchlorazole
B-623 diflufenzopyr-sodium fenchlorazole
B-624 clomazone fenchlorazole
B-625 diflufenican fenchlorazole
B-626 fluorochloridone fenchlorazole
B-627 isoxaflutol fenchlorazole
B-628 mesotrione fenchlorazole
B-629 picolinafen fenchlorazole
B-630 sulcotrione fenchlorazole
B-631 tefuryltrione fenchlorazole
B-632 tembotrione fenchlorazole
B-633 topramezone fenchlorazole
B-634 H-7 fenchlorazole
B-635 atrazine fenchlorazole
B-636 diuron fenchlorazole
B-637 fluometuron fenchlorazole
B-638 hexazinone fenchlorazole
B-639 isoproturon fenchlorazole
B-640 metribuzin fenchlorazole
B-641 propanil fenchlorazole
B-642 terbuthylazine fenchlorazole
B-643 paraquat dichloride fenchlorazole
B-644 flumioxazin fenchlorazole
B-645 oxyfluorfen fenchlorazole
B-646 saflufenacil fenchlorazole
B-647 sulfentrazone fenchlorazole
B-648 H-1 fenchlorazole
B-649 H-2 fenchlorazole
B-650 glyphosate fenchlorazole
B-651 glyphosate-isopropylammonium fenchlorazole
B-652 glyphosate-trimesium (sulfosate) fenchlorazole
B-653 glufosinate fenchlorazole
B-654 glufosinate-ammonium fenchlorazole
B-655 pendimethalin fenchlorazole Herbicide(s) B Safener C
B-656 trifluralin fenchlorazole
B-657 acetochlor fenchlorazole
B-658 cafenstrole fenchlorazole
B-659 dimethenamid-P fenchlorazole
B-660 fentrazamide fenchlorazole
B-661 flufenacet fenchlorazole
B-662 mefenacet fenchlorazole
B-663 metazachlor fenchlorazole
B-664 metolachlor-S fenchlorazole
B-665 pyroxasulfone fenchlorazole
B-666 isoxaben fenchlorazole
B-667 dymron fenchlorazole
B-668 indanofan fenchlorazole
B-669 oxaziclomefone fenchlorazole
B-670 triaziflam fenchlorazole
B-671 atrazine + H-1 fenchlorazole
B-672 atrazine + glyphosate fenchlorazole
B-673 atrazine + mesotrione fenchlorazole
B-674 atrazine + nicosulfuron fenchlorazole
B-675 atrazine + tembotrione fenchlorazole
B-676 atrazine + topramezone fenchlorazole
B-677 clomazone + glyphosate fenchlorazole
B-678 diflufenican + dodinafop-propargyl fenchlorazole
B-679 diflufenican + fenoxaprop-P-ethyl fenchlorazole
B-680 diflufenican + flupyrsulfuron-methyl-sodium fenchlorazole
B-681 diflufenican + glyphosate fenchlorazole
B-682 diflufenican + mesosulfuron-methyl fenchlorazole
B-683 diflufenican + pinoxaden fenchlorazole
B-684 diflufenican + pyroxsulam fenchlorazole
B-685 flumetsulam + glyphosate fenchlorazole
B-686 flumioxazin + glyphosate fenchlorazole
B-687 imazapic + glyphosate fenchlorazole
B-688 imazethapyr + glyphosate fenchlorazole
B-689 isoxaflutol + H-1 fenchlorazole
B-690 isoxaflutol + glyphosate fenchlorazole
B-691 metazachlor + H-1 fenchlorazole
B-692 metazachlor + glyphosate fenchlorazole
B-693 metazachlor + mesotrione fenchlorazole
B-694 metazachlor + nicosulfuron fenchlorazole
B-695 metazachlor + terbuthylazine fenchlorazole Herbicide(s) B Safener C
B-696 metazachlor + topramezone fenchlorazole
B-697 metribuzin + glyphosate fenchlorazole
B-698 pendimethalin + H-1 fenchlorazole
B-699 pendimethalin + clodinafop-propargyl fenchlorazole
B-700 pendimethalin + fenoxaprop-P-ethyl fenchlorazole
B-701 pendimethalin + flupyrsulfuron-methyl-sodium fenchlorazole
B-702 pendimethalin + glyphosate fenchlorazole
B-703 pendimethalin + mesosulfuron-methyl fenchlorazole
B-704 pendimethalin + mesotrione fenchlorazole
B-705 pendimethalin + nicosulfuron fenchlorazole
B-706 pendimethalin + pinoxaden fenchlorazole
B-707 pendimethalin + pyroxsulam fenchlorazole
B-708 pendimethalin + tembotrione fenchlorazole
B-709 pendimethalin + topramezone fenchlorazole
B-710 pyroxasulfone + tembotrione fenchlorazole
B-71 1 pyroxasulfone + topramezone fenchlorazole
B-712 sulfentrazone + glyphosate fenchlorazole
B-713 terbuthylazine + H-1 fenchlorazole
B-714 terbuthylazine + foramsulfuron fenchlorazole
B-715 terbuthylazine + glyphosate fenchlorazole
B-716 terbuthylazine + mesotrione fenchlorazole
B-717 terbuthylazine + nicosulfuron fenchlorazole
B-718 terbuthylazine + tembotrione fenchlorazole
B-719 terbuthylazine + topramezone fenchlorazole
B-720 trifluralin + glyphosate fenchlorazole
B-721 clodinafop-propargyl isoxadifen
B-722 cycloxydim isoxadifen
B-723 cyhalofop-butyl isoxadifen
B-724 fenoxaprop-P-ethyl isoxadifen
B-725 pinoxaden isoxadifen
B-726 profoxydim isoxadifen
B-727 tepraloxydim isoxadifen
B-728 tralkoxydim isoxadifen
B-729 esprocarb isoxadifen
B-730 prosulfocarb isoxadifen
B-731 thiobencarb isoxadifen
B-732 triallate isoxadifen
B-733 bensulfuron-methyl isoxadifen
B-734 bispyribac-sodium isoxadifen
B-735 cyclosulfamuron isoxadifen Herbicide(s) B Safener C
B-736 flumetsulam isoxadifen
B-737 flupyrsulfuron-methyl-sodium isoxadifen
B-738 foramsulfuron isoxadifen
B-739 imazamox isoxadifen
B-740 imazapic isoxadifen
B-741 imazapyr isoxadifen
B-742 imazaquin isoxadifen
B-743 imazethapyr isoxadifen
B-744 imazosulfuron isoxadifen
B-745 iodosulfuron-methyl-sodium isoxadifen
B-746 mesosulfuron isoxadifen
B-747 nicosulfuron isoxadifen
B-748 penoxsulam isoxadifen
B-749 propoxycarbazone-sodium isoxadifen
B-750 pyrazosulfuron-ethyl isoxadifen
B-751 pyroxsulam isoxadifen
B-752 rimsulfuron isoxadifen
B-753 sulfosulfuron isoxadifen
B-754 thiencarbazone-methyl isoxadifen
B-755 tritosulfuron isoxadifen
B-756 2,4-D and its salts and esters isoxadifen
B-757 aminopyralid and its salts and esters isoxadifen
B-758 clopyralid and its salts and esters isoxadifen
B-759 dicamba and its salts and esters isoxadifen
B-760 fluroxypyr-meptyl isoxadifen
B-761 quinclorac isoxadifen
B-762 quinmerac isoxadifen
B-763 H-9 isoxadifen
B-764 diflufenzopyr isoxadifen
B-765 diflufenzopyr-sodium isoxadifen
B-766 clomazone isoxadifen
B-767 diflufenican isoxadifen
B-768 fluorochloridone isoxadifen
B-769 isoxaflutol isoxadifen
B-770 mesotrione isoxadifen
B-771 picolinafen isoxadifen
B-772 sulcotrione isoxadifen
B-773 tefuryltrione isoxadifen
B-774 tembotrione isoxadifen
B-775 topramezone isoxadifen Herbicide(s) B Safener C
B-776 H-7 isoxadifen
B-777 atrazine isoxadifen
B-778 diuron isoxadifen
B-779 fluometuron isoxadifen
B-780 hexazinone isoxadifen
B-781 isoproturon isoxadifen
B-782 metribuzin isoxadifen
B-783 propanil isoxadifen
B-784 terbuthylazine isoxadifen
B-785 paraquat dichloride isoxadifen
B-786 flumioxazin isoxadifen
B-787 oxyfluorfen isoxadifen
B-788 saflufenacil isoxadifen
B-789 sulfentrazone isoxadifen
B-790 H-1 isoxadifen
B-791 H-2 isoxadifen
B-792 glyphosate isoxadifen
B-793 glyphosate-isopropylammonium isoxadifen
B-794 glyphosate-trimesium (sulfosate) isoxadifen
B-795 glufosinate isoxadifen
B-796 glufosinate-ammonium isoxadifen
B-797 pendimethalin isoxadifen
B-798 trifluralin isoxadifen
B-799 acetochlor isoxadifen
B-800 cafenstrole isoxadifen
B-801 dimethenamid-P isoxadifen
B-802 fentrazamide isoxadifen
B-803 flufenacet isoxadifen
B-804 mefenacet isoxadifen
B-805 metazachlor isoxadifen
B-806 metolachlor-S isoxadifen
B-807 pyroxasulfone isoxadifen
B-808 isoxaben isoxadifen
B-809 dymron isoxadifen
B-810 indanofan isoxadifen
B-81 1 oxaziclomefone isoxadifen
B-812 triaziflam isoxadifen
B-813 atrazine + H-1 isoxadifen
B-814 atrazine + glyphosate isoxadifen
B-815 atrazine + mesotrione isoxadifen Herbicide(s) B Safener C
B-816 atrazine + nicosulfuron isoxadifen
B-817 atrazine + tembotrione isoxadifen
B-818 atrazine + topramezone isoxadifen
B-819 clomazone + glyphosate isoxadifen
B-820 diflufenican + clodinafop-propargyl isoxadifen
B-821 diflufenican + fenoxaprop-P-ethyl isoxadifen
B-822 diflufenican + flupyrsulfuron-methyl-sodium isoxadifen
B-823 diflufenican + glyphosate isoxadifen
B-824 diflufenican + mesosulfuron-methyl isoxadifen
B-825 diflufenican + pinoxaden isoxadifen
B-826 diflufenican + pyroxsulam isoxadifen
B-827 flumetsulam + glyphosate isoxadifen
B-828 flumioxazin + glyphosate isoxadifen
B-829 imazapic + glyphosate isoxadifen
B-830 imazethapyr + glyphosate isoxadifen
B-831 isoxaflutol + H-1 isoxadifen
B-832 isoxaflutol + glyphosate isoxadifen
B-833 metazachlor + H-1 isoxadifen
B-834 metazachlor + glyphosate isoxadifen
B-835 metazachlor + mesotrione isoxadifen
B-836 metazachlor + nicosulfuron isoxadifen
B-837 metazachlor + terbuthylazine isoxadifen
B-838 metazachlor + topramezone isoxadifen
B-839 metribuzin + glyphosate isoxadifen
B-840 pendimethalin + H-1 isoxadifen
B-841 pendimethalin + clodinafop-propargyl isoxadifen
B-842 pendimethalin + fenoxaprop-P-ethyl isoxadifen
B-843 pendimethalin + flupyrsulfuron-methyl-sodium isoxadifen
B-844 pendimethalin + glyphosate isoxadifen
B-845 pendimethalin + mesosulfuron-methyl isoxadifen
B-846 pendimethalin + mesotrione isoxadifen
B-847 pendimethalin + nicosulfuron isoxadifen
B-848 pendimethalin + pinoxaden isoxadifen
B-849 pendimethalin + pyroxsulam isoxadifen
B-850 pendimethalin + tembotrione isoxadifen
B-851 pendimethalin + topramezone isoxadifen
B-852 pyroxasulfone + tembotrione isoxadifen
B-853 pyroxasulfone + topramezone isoxadifen
B-854 sulfentrazone + glyphosate isoxadifen
B-855 terbuthylazine + H-1 isoxadifen Herbicide(s) B Safener C
B-856 terbuthylazine + foramsulfuron isoxadifen
B-857 terbuthylazine + glyphosate isoxadifen
B-858 terbuthylazine + mesotrione isoxadifen
B-859 terbuthylazine + nicosulfuron isoxadifen
B-860 terbuthylazine + tembotrione isoxadifen
B-861 terbuthylazine + topramezone isoxadifen
B-862 trifluralin + glyphosate isoxadifen
B-863 clodinafop-propargyl mefenpyr
B-864 cycloxydim mefenpyr
B-865 cyhalofop-butyl mefenpyr
B-866 fenoxaprop-P-ethyl mefenpyr
B-867 pinoxaden mefenpyr
B-868 profoxydim mefenpyr
B-869 tepraloxydim mefenpyr
B-870 tralkoxydim mefenpyr
B-871 esprocarb mefenpyr
B-872 prosulfocarb mefenpyr
B-873 thiobencarb mefenpyr
B-874 triallate mefenpyr
B-875 bensulfuron-methyl mefenpyr
B-876 bispyribac-sodium mefenpyr
B-877 cyclosulfamuron mefenpyr
B-878 flumetsulam mefenpyr
B-879 flupyrsulfuron-methyl-sodium mefenpyr
B-880 foramsulfuron mefenpyr
B-881 imazamox mefenpyr
B-882 imazapic mefenpyr
B-883 imazapyr mefenpyr
B-884 imazaquin mefenpyr
B-885 imazethapyr mefenpyr
B-886 imazosulfuron mefenpyr
B-887 iodosulfuron-methyl-sodium mefenpyr
B-888 mesosulfuron mefenpyr
B-889 nicosulfuron mefenpyr
B-890 penoxsulam mefenpyr
B-891 propoxycarbazone-sodium mefenpyr
B-892 pyrazosulfuron-ethyl mefenpyr
B-893 pyroxsulam mefenpyr
B-894 rimsulfuron mefenpyr
B-895 sulfosulfuron mefenpyr Herbicide(s) B Safener C
B-896 thiencarbazone-methyl mefenpyr
B-897 tritosulfuron mefenpyr
B-898 2,4-D and its salts and esters mefenpyr
B-899 aminopyralid and its salts and esters mefenpyr
B-900 clopyralid and its salts and esters mefenpyr
B-901 dicamba and its salts and esters mefenpyr
B-902 fluroxypyr-meptyl mefenpyr
B-903 quinclorac mefenpyr
B-904 quinmerac mefenpyr
B-905 H-9 mefenpyr
B-906 diflufenzopyr mefenpyr
B-907 diflufenzopyr-sodium mefenpyr
B-908 clomazone mefenpyr
B-909 diflufenican mefenpyr
B-910 fluorochloridone mefenpyr
B-91 1 isoxaflutol mefenpyr
B-912 mesotrione mefenpyr
B-913 picolinafen mefenpyr
B-914 sulcotrione mefenpyr
B-915 tefuryltrione mefenpyr
B-916 tembotrione mefenpyr
B-917 topramezone mefenpyr
B-918 H-7 mefenpyr
B-919 atrazine mefenpyr
B-920 diuron mefenpyr
B-921 fluometuron mefenpyr
B-922 hexazinone mefenpyr
B-923 isoproturon mefenpyr
B-924 metribuzin mefenpyr
B-925 propanil mefenpyr
B-926 terbuthylazine mefenpyr
B-927 paraquat dichloride mefenpyr
B-928 flumioxazin mefenpyr
B-929 oxyfluorfen mefenpyr
B-930 saflufenacil mefenpyr
B-931 sulfentrazone mefenpyr
B-932 H-1 mefenpyr
B-933 H-2 mefenpyr
B-934 glyphosate mefenpyr
B-935 glyphosate-isopropylammonium mefenpyr Herbicide(s) B Safener C
B-936 glyphosate-trimesium (sulfosate) mefenpyr
B-937 glufosinate mefenpyr
B-938 glufosinate-ammonium mefenpyr
B-939 pendimethalin mefenpyr
B-940 trifluralin mefenpyr
B-941 acetochlor mefenpyr
B-942 cafenstrole mefenpyr
B-943 dimethenamid-P mefenpyr
B-944 fentrazamide mefenpyr
B-945 flufenacet mefenpyr
B-946 mefenacet mefenpyr
B-947 metazachlor mefenpyr
B-948 metolachlor-S mefenpyr
B-949 pyroxasulfone mefenpyr
B-950 isoxaben mefenpyr
B-951 dymron mefenpyr
B-952 indanofan mefenpyr
B-953 oxaziclomefone mefenpyr
B-954 triaziflam mefenpyr
B-955 atrazine + H-1 mefenpyr
B-956 atrazine + glyphosate mefenpyr
B-957 atrazine + mesotrione mefenpyr
B-958 atrazine + nicosulfuron mefenpyr
B-959 atrazine + tembotrione mefenpyr
B-960 atrazine + topramezone mefenpyr
B-961 clomazone + glyphosate mefenpyr
B-962 diflufenican + clodinafop-propargyl mefenpyr
B-963 diflufenican + fenoxaprop-P-ethyl mefenpyr
B-964 diflufenican + flupyrsulfuron-methyl-sodium mefenpyr
B-965 diflufenican + glyphosate mefenpyr
B-966 diflufenican + mesosulfuron-methyl mefenpyr
B-967 diflufenican + pinoxaden mefenpyr
B-968 diflufenican + pyroxsulam mefenpyr
B-969 flumetsulam + glyphosate mefenpyr
B-970 flumioxazin + glyphosate mefenpyr
B-971 imazapic + glyphosate mefenpyr
B-972 imazethapyr + glyphosate mefenpyr
B-973 isoxaflutol + H-1 mefenpyr
B-974 isoxaflutol + glyphosate mefenpyr
B-975 metazachlor + H-1 mefenpyr Herbicide(s) B Safener C
B-976 metazachlor + glyphosate mefenpyr
B-977 metazachlor + mesotrione mefenpyr
B-978 metazachlor + nicosulfuron mefenpyr
B-979 metazachlor + terbuthylazine mefenpyr
B-980 metazachlor + topramezone mefenpyr
B-981 metribuzin + glyphosate mefenpyr
B-982 pendimethalin + H-1 mefenpyr
B-983 pendimethalin + clodinafop-propargyl mefenpyr
B-984 pendimethalin + fenoxaprop-P-ethyl mefenpyr
B-985 pendimethalin + flupyrsulfuron-methyl-sodium mefenpyr
B-986 pendimethalin + glyphosate mefenpyr
B-987 pendimethalin + mesosulfuron-methyl mefenpyr
B-988 pendimethalin + mesotrione mefenpyr
B-989 pendimethalin + nicosulfuron mefenpyr
B-990 pendimethalin + pinoxaden mefenpyr
B-991 pendimethalin + pyroxsulam mefenpyr
B-992 pendimethalin + tembotrione mefenpyr
B-993 pendimethalin + topramezone mefenpyr
B-994 pyroxasulfone + tembotrione mefenpyr
B-995 pyroxasulfone + topramezone mefenpyr
B-996 sulfentrazone + glyphosate mefenpyr
B-997 terbuthylazine + H-1 mefenpyr
B-998 terbuthylazine + foramsulfuron mefenpyr
B-999 terbuthylazine + glyphosate mefenpyr
B-1000 terbuthylazine + mesotrione mefenpyr
B-1001 terbuthylazine + nicosulfuron mefenpyr
B-1002 terbuthylazine + tembotrione mefenpyr
B-1003 terbuthylazine + topramezone mefenpyr
B-1004 trifluralin + glyphosate mefenpyr
B-1005 clodinafop-propargyl H-12
B-1006 cycloxydim H-12
B-1007 cyhalofop-butyl H-12
B-1008 fenoxaprop-P-ethyl H-12
B-1009 pinoxaden H-12
B-1010 profoxydim H-12
B-101 1 tepraloxydim H-12
B-1012 tralkoxydim H-12
B-1013 esprocarb H-12
B-1014 prosulfocarb H-12
B-1015 thiobencarb H-12 Herbicide(s) B Safener C
B-1016 triallate H-12
B-1017 bensulfuron-methyl H-12
B-1018 bispyribac-sodium H-12
B-1019 cyclosulfamuron H-12
B-1020 flumetsulam H-12
B-1021 flupyrsulfuron-methyl-sodium H-12
B-1022 foramsulfuron H-12
B-1023 imazamox H-12
B-1024 imazapic H-12
B-1025 imazapyr H-12
B-1026 imazaquin H-12
B-1027 imazethapyr H-12
B-1028 imazosulfuron H-12
B-1029 iodosulfuron-methyl-sodium H-12
B-1030 mesosulfuron H-12
B-1031 nicosulfuron H-12
B-1032 penoxsulam H-12
B-1033 propoxycarbazone-sodium H-12
B-1034 pyrazosulfuron-ethyl H-12
B-1035 pyroxsulam H-12
B-1036 rimsulfuron H-12
B-1037 sulfosulfuron H-12
B-1038 thiencarbazone-methyl H-12
B-1039 tritosulfuron H-12
B-1040 2,4-D and its salts and esters H-12
B-1041 aminopyralid and its salts and esters H-12
B-1042 clopyralid and its salts and esters H-12
B-1043 dicamba and its salts and esters H-12
B-1044 fluroxypyr-meptyl H-12
B-1045 quinclorac H-12
B-1046 quinmerac H-12
B-1047 H-9 H-12
B-1048 diflufenzopyr H-12
B-1049 diflufenzopyr-sodium H-12
B-1050 clomazone H-12
B-1051 diflufenican H-12
B-1052 fluorochloridone H-12
B-1053 isoxaflutol H-12
B-1054 mesotrione H-12
B-1055 picolinafen H-12 Herbicide(s) B Safener C
B-1056 sulcotrione H-12
B-1057 tefuryltrione H-12
B-1058 tembotrione H-12
B-1059 topramezone H-12
B-1060 H-7 H-12
B-1061 atrazine H-12
B-1062 diuron H-12
B-1063 fluometuron H-12
B-1064 hexazinone H-12
B-1065 isoproturon H-12
B-1066 metribuzin H-12
B-1067 propanil H-12
B-1068 terbuthylazine H-12
B-1069 paraquat dichloride H-12
B-1070 flumioxazin H-12
B-1071 oxyfluorfen H-12
B-1072 saflufenacil H-12
B-1073 sulfentrazone H-12
B-1074 H-1 H-12
B-1075 H-2 H-12
B-1076 glyphosate H-12
B-1077 glyphosate-isopropylammonium H-12
B-1078 glyphosate-trimesium (sulfosate) H-12
B-1079 glufosinate H-12
B-1080 glufosinate-ammonium H-12
B-1081 pendimethalin H-12
B-1082 trifluralin H-12
B-1083 acetochlor H-12
B-1084 cafenstrole H-12
B-1085 dimethenamid-P H-12
B-1086 fentrazamide H-12
B-1087 flufenacet H-12
B-1088 mefenacet H-12
B-1089 metazachlor H-12
B-1090 metolachlor-S H-12
B-1091 pyroxasulfone H-12
B-1092 isoxaben H-12
B-1093 dymron H-12
B-1094 indanofan H-12
B-1095 oxaziclomefone H-12 Herbicide(s) B Safener C
B-1096 triaziflam H-12
B-1097 atrazine + H-1 H-12
B-1098 atrazine + glyphosate H-12
B-1099 atrazine + mesotrione H-12
B-1100 atrazine + nicosulfuron H-12
B-1101 atrazine + tembotrione H-12
B-1102 atrazine + topramezone H-12
B-1103 clomazone + glyphosate H-12
B-1104 diflufenican + clodinafop-propargyl H-12
B-1105 diflufenican + fenoxaprop-P-ethyl H-12
B-1106 diflufenican + flupyrsulfuron-methyl-sodium H-12
B-1107 diflufenican + glyphosate H-12
B-1108 diflufenican + mesosulfuron-methyl H-12
B-1109 diflufenican + pinoxaden H-12
B-1110 diflufenican + pyroxsulam H-12
B-1111 flumetsulam + glyphosate H-12
B-1112 flumioxazin + glyphosate H-12
B-1113 imazapic + glyphosate H-12
B-1114 imazethapyr + glyphosate H-12
B-1115 isoxaflutol + H-1 H-12
B-1116 isoxaflutol + glyphosate H-12
B-1117 metazachlor + H-1 H-12
B-1118 metazachlor + glyphosate H-12
B-1119 metazachlor + mesotrione H-12
B-1120 metazachlor + nicosulfuron H-12
B-1121 metazachlor + terbuthylazine H-12
B-1122 metazachlor + topramezone H-12
B-1123 metribuzin + glyphosate H-12
B-1124 pendimethalin + H-1 H-12
B-1125 pendimethalin + clodinafop-propargyl H-12
B-1126 pendimethalin + fenoxaprop-P-ethyl H-12
B-1127 pendimethalin + flupyrsulfuron-methyl-sodium H-12
B-1128 pendimethalin + glyphosate H-12
B-1129 pendimethalin + mesosulfuron-methyl H-12
B-1130 pendimethalin + mesotrione H-12
B-1131 pendimethalin + nicosulfuron H-12
B-1132 pendimethalin + pinoxaden H-12
B-1133 pendimethalin + pyroxsulam H-12
B-1134 pendimethalin + tembotrione H-12
B-1135 pendimethalin + topramezone H-12 Herbicide(s) B Safener C
B-1136 pyroxasulfone + tembotrione H-12
B-1137 pyroxasulfone + topramezone H-12
B-1138 sulfentrazone + glyphosate H-12
B-1139 terbuthylazine + H-1 H-12
B-1140 terbuthylazine + foramsulfuron H-12
B-1141 terbuthylazine + glyphosate H-12
B-1142 terbuthylazine + mesotrione H-12
B-1143 terbuthylazine + nicosulfuron H-12
B-1144 terbuthylazine + tembotrione H-12
B-1145 terbuthylazine + topramezone H-12
B-1146 trifluralin + glyphosate H-12
B-1147 2-1 —
B-1148 2-2 —
B-1149 2-3 —
B-1150 2-4 —
B-1151 2-5 —
B-1152 2-6 —
B-1153 2-7 —
B-1154 2-8 —
B-1155 2-9 —
B-1156 2-1 benoxacor
B-1157 2-2 benoxacor
B-1158 2-3 benoxacor
B-1159 2-4 benoxacor
B-1160 2-5 benoxacor
B-1161 2-6 benoxacor
B-1162 2-7 benoxacor
B-1163 2-8 benoxacor
B-1164 2-9 benoxacor
B-1165 2-1 cloquintocet
B-1166 2-2 cloquintocet
B-1167 2-3 cloquintocet
B-1168 2-4 cloquintocet
B-1169 2-5 cloquintocet
B-1170 2-6 cloquintocet
B-1171 2-7 cloquintocet
B-1172 2-8 cloquintocet
B-1173 2-9 cloquintocet
B-1174 2-1 cyprosulfamide
B-1175 2-2 cyprosulfamide Herbicide(s) B Safener C
B-1176 2-3 cyprosulfamide
B-1177 2-4 cyprosulfamide
B-1178 2-5 cyprosulfamide
B-1179 2-6 cyprosulfamide
B-1180 2-7 cyprosulfamide
B-1181 2-8 cyprosulfamide
B-1182 2-9 cyprosulfamide
B-1183 2-1 dichlormid
B-1184 2-2 dichlormid
B-1185 2-3 dichlormid
B-1186 2-4 dichlormid
B-1187 2-5 dichlormid
B-1188 2-6 dichlormid
B-1189 2-7 dichlormid
B-1190 2-8 dichlormid
B-1191 2-9 dichlormid
B-1192 2-1 fenchlorazole
B-1193 2-2 fenchlorazole
B-1194 2-3 fenchlorazole
B-1195 2-4 fenchlorazole
B-1196 2-5 fenchlorazole
B-1197 2-6 fenchlorazole
B-1198 2-7 fenchlorazole
B-1199 2-8 fenchlorazole
B-1200 2-9 fenchlorazole
B-1201 2-1 isoxadifen
B-1202 2-2 isoxadifen
B-1203 2-3 isoxadifen
B-1204 2-4 isoxadifen
B-1205 2-5 isoxadifen
B-1206 2-6 isoxadifen
B-1207 2-7 isoxadifen
B-1208 2-8 isoxadifen
B-1209 2-9 isoxadifen
B-1210 2-1 mefenpyr
B-1211 2-2 mefenpyr
B-1212 2-3 mefenpyr
B-1213 2-4 mefenpyr
B-1214 2-5 mefenpyr
B-1215 2-6 mefenpyr Herbicide(s) B Safener C
B-1216 2-7 mefenpyr
B-1217 2-8 mefenpyr
B-1218 2-9 mefenpyr
B-1219 2-1 H-1 1
B-1220 2-2 H-1 1
B-1221 2-3 H-1 1
B-1222 2-4 H-1 1
B-1223 2-5 H-1 1
B-1224 2-6 H-1 1
B-1225 2-7 H-1 1
B-1226 2-8 H-1 1
B-1227 2-9 H-1 1
B-1228 2-1 H-12
B-1229 2-2 H-12
B-1230 2-3 H-12
B-1231 2-4 H-12
B-1232 2-5 H-12
B-1233 2-6 H-12
B-1234 2-7 H-12
B-1235 2-8 H-12
B-1236 2-9 H-12
The compounds of formula I and the compositions according to the invention may also have a plant-strengthening action. Accordingly, they are suitable for mobilizing the defense sys- tern of the plants against attack by unwanted microorganisms, such as harmful fungi, but also viruses and bacteria. Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances which are capable of stimulating the defense system of treated plants in such a way that, when subsequently inoculated by unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms.
The compounds of formula I can be employed for protecting plants against attack by unwanted microorganisms within a certain period of time after the treatment. The period of time within which their protection is effected generally extends from 1 to 28 days, preferably from 1 to 14 days, after the treatment of the plants with the compounds of formula I, or, after treatment of the seed, for up to 9 months after sowing.
The compounds of formula I and the compositions according to the invention are also suitable for increasing the harvest yield.
Moreover, they have reduced toxicity and are tolerated well by the plants. Examples
The preparation of the compounds of formula I is illustrated by examples; however, the subject matter of the present invention is not limited to the examples given.
I. Synthesis examples
With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds I. The compounds obtained in this manner are listed in the table that follows, together with physical data.
The products shown below were characterized by determination of the melting point, NMR spectroscopy or the masses ([m/z]) determined by HPLC-MS spectrometry.
HPLC-MS = high performance liquid chromatography coupled with mass spectrometry; HPLC column: 15 RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm; mobile phase: acetonitrile + 0.1 % trifluoroacetic acid (TFA)/water + 0.1 % TFA, using a gradient from 5:95t o 100:0 over 5 minutes at 40'C, flow rate 1 .8 ml/min.
MS: quadrupole electrospray ionization, 80 V (positive mode)
Example 1 : 2,4-dichloro-6-fluoro-3-(2-methylsulfanylethoxy)-N-(1 -methyltetrazol-5-yl)benzamide
Figure imgf000135_0001
2,4-dichloro-6-fluoro-3-hydroxy-N-(1 -methyltetrazol-5-yl)benzamide (0,4 g, 0,001 mol) were dissolved in 2 ml dimethylformamide (DMF). Powdered potassium carbonate (0,27 g, 0,002 mol) was suspended in this solution. 1 -bromo-2-methylsulfanyl-ethane (0,167 g, 0,001 mol) was added and the mixture was heated up to 60°C for overnight. DMF was evaporated at 60°C. Water was added to the residue and made acidic with 2 N hydrochloric acid. The precipitated crude product purified by column chromatography to yield 0,147 g of a pale white solid. .LC-MS (M+H): 380
1 H NMR (400 MHz, d8-THF), δ 2,18 (s, 3H), 2,84 (t, 2H), 4,03 (s, 3H), 4,30 (t, 2H), 7,54 (d, 1 H), 1 1 ,17(br s, 1 H)
The compounds listed below in tables I, II and III can be prepared similarly to the examples mentioned above.
Figure imgf000136_0001
I, wherein Q is Q\ R4 is H and R5 is F
Table I:
Figure imgf000136_0002
Figure imgf000137_0001
Figure imgf000138_0001
Figure imgf000139_0001
I, wherein Q is Q1 , R4 is H and R5 is F
Table II:
Figure imgf000139_0003
Figure imgf000139_0002
(Compound I, wherein Q is Q1, R4 is H and R5 is CI)
Table
Figure imgf000139_0004
II. Use examples
The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:
The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.
For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The con- tainers 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 had been impaired by the active ingredients.
For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. Depending on the species, the plants were kept at 10 - 25°C or 20 - 25°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 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 250g/ha the following compounds were tested in post-emergence tests against ALOMY (Alopecurus myosuroiedes), ECHCG (Echinocloa crus-galli), AMARE (Amaran- thus retroflexus) and CHEAL (Chenopodium album) and showed a control of at least 85 %:
Compounds I.A.V.2, I.A.V.5, I.A.V.6, I.A.V.7, I.A.V.9, I.A.V.1 1 , I.A.V.74, I.A.V.13, I.A.V.17, I.A.V.26, I.A.V.33, I.A.V.35, I.A.V.36, I.A.V.949.

Claims

Claims
1 . A compound of formula I ,
Figure imgf000141_0001
wherein
Q is Q1 or Q2 or Q3 or Q4,
Figure imgf000141_0002
(Q ) (Q2) (Q3) (Q4)
where the arrow denotes the attachment point to the remainder of the molecule;
R1 is selected from the group consisting of cyano, halogen, nitro, Ci-Cs-alkyl, C2-C8- alkenyl, C2-C8-alkynyl, Ci-Cs-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C4-alkyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C6-haloalkoxy and R1b- S(0)k-Zi;
R2 is selected from the group consisting of Ci-C6-alkyl-S(0)n-Z2, Ci-C6-haloalkyl-S(0)n- Z2, C3-C6-cycloalkyl-S(0)n-Z2, heterocyclyl-Z2a, where heterocyclyl is a 5- or 6- membered saturated, S(0)n-containing heterocycle; phenyl-S(0)n-Z2, and heteroaryl-S(0)n-Z2, where the cyclic groups of the four aforementioned radicals are unsubstituted or substituted by 1 ,
2,
3 or 4 groups selected from the group consisting of halogen, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and methylsulfonyl;
R3 is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, hydroxy-Z3, Ci-C6-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, C3-Cio-cycloalkyl-Z3, C3-C6- cycloalkenyl-Z3, C3-Cio-cycloalkoxy-Z3, C3-Cio-cycloalkyl-Ci-C2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated, Ci-C4-cyanoalkyl, Ci-Cs-haloalkyl, C2-C8-haloalkenyl, C3- Cs-haloalkynyl, Ci-Cs-alkoxy-Z3, d-Cs-haloalkoxy-Z3, Ci-C4-alkoxy-Ci-C4-alkoxy-Z3, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z3, C2-C8-alkenyloxy-Z3, C2-C8-alkynyloxy-Z3, C2-C8- haloalkenyloxy-Z3, C3-C8-haloalkynyloxy-Z3, R3b-S(0)k-Z3, R3c-C(0)-Z3, R3dO-C(0)- Z3, R3dO-N=CH-Z3, R3eR3fN-C(0)-Z3, R¾R3hN-Z3, R22C(0)0-Z3, R25OC(0)0-Z3, (R22)2NC(0)0-Z3, R25S(0)20-Z3, R22OS(0)2-Z3, (R22)2NS(0)2-Z3, R25OC(0)N(R22)-Z3, (R22)2NC(0)N(R22)-Z3, (R22)2NS(0)2N(R22)-Z3, (OH)2P(0)-Z3, (Ci-C4-alkoxy)2P(0)-Z3, phenyl-Z3a, and heterocyclyl-Z3a, where heterocyclyl is a 3-,
4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where cyclic groups in phenyl-Z3a and heterocyclyl-Z3a are unsubstituted or substituted by 1 , 2, 3 or 4 groups R21 which are identical or different;
R4 is selected from the group consisting of hydrogen, halogen, cyano-Z1, Ci-Cs-alkyl, nitro, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-Cs-haloalkyl, Ci-C3-alkylamino, C1-C3- dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-C3-alkylcarbonyl, d-Cs-alkoxy, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1, Ci-C4-alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C C6-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkoxy-Z1, Rb-S(0)k-Z1, phenoxy-Z and heterocyclyloxy-Z, where heterocyclyloxy is an oxygen-bound 5- or 6- membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocy- clyloxy are unsubstituted or substituted by 1 , 2, 3 or 4 groups R11 which are identical or different;
R5 is halogen, cyano-Z1, nitro, Ci-Cs-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4- alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are un- substituted or partially or completely halogenated; C2-Cs-alkenyl, C2-Cs-alkynyl, Ci-
Cs-haloalkyl, Ci-C3-alkylamino, Ci-C3-dialkylamino, Ci-C3-alkylamino-S(0)k, Ci-Cs- alkyl carbonyl, Ci-Cs-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy- Z1, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-haloalkoxy, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy- Ci-C4-alkoxy-Z1, R1b-S(0)k-Z1, phenoxy-Z1 and heterocyclyloxy-Z1, where heterocyclyloxy is an oxygen-bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubsti- tuted or substituted by 1 , 2, 3 or 4 groups R11 which are identical or different;
R6 is selected from the group consisting of Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7- cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups of the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-
C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Rb-S(0)n-Ci-C3-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R11, R21, independently of each other, are selected from the group consisting of cyano, halogen, nitro, Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy, Ci- C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-haloalkoxy-Ci-C4-alkyl, Ci- C4-alkoxy-Ci-C4-alkoxy, C3-C7-cycloalkoxy and Ci-C6-haloalkoxy, or two radicals R21 bound to the same carbon atom together may form a group =0;
Z1, Z3, independently of each other, are selected from the group consisting of a covalent bond and Ci-C4-alkanediyl;
Z2 is Ci-C3-alkanediyl,
which is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl; is a covalent bond or Ci-C3-alkanediyl,
where the Ci-C3-alkanediyl group is unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of Ci C4-alkyl and Ci-C4-haloalkyl;
Z3a is selected from the group consisting of a covalent bond, Ci-C4-alkanediyl, O-C1-C4- alkanediyl, Ci-C4-alkanediyl-0 and Ci-C4-alkanediyl-0-Ci-C4-alkanediyl;
Rb, R1b, R3b, independently of each other, are selected from the group consisting of C1-C6- alkyl, C3-C7-cycloalkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C3-C6-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6- membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1 , 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R3c is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; C1-C6- haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S(0)n-Ci-C4- alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci-C6-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R3d is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforemen- tioned radicals are unsubstituted or partially or completely halogenated; C1-C6- haloalkyl, Ci-C6-alkoxy, C2-C6-alkenyl, Ci-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkyl-S(0)n-Ci-C4- alkyl, Ci-C4-alkylamino-Ci-C4-alkyl, Ci-C4-dialkylamino-Ci-C4-alkyl, Ci-C6-cyanoalkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
R3c and R3d, together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6- or 7-membered, saturated or unsaturated heterocyclic radical which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; R3e, R3f, independently of each other, are selected from the group consisting of hydrogen,
Ci-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7- cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated; Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C3-C6-haloalkynyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl, where phe- nyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
R3e and R3f , together with the nitrogen atom to which they are bound, may form a 4-, 5-, 6- or 7-membered, saturated or unsaturated heterocyclic radical which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R¾ is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforemen- tioned radicals are unsubstituted or partially or completely halogenated; C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen,
Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R3h is selected from the group consisting of hydrogen, Ci-C6-alkyl, C3-C7-cycloalkyl, C3- C7-cycloalkyl-Ci-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforemen- tioned radicals are unsubstituted or partially or completely halogenated; C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4- alkoxy-Ci-C4-alkyl, Ci-C4-alkylsulfonyl, Ci-C4-alkylcarbonyl, a radical C(0)Rk, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; or
R¾ and R3h, together with the nitrogen atom to which they are bound, may form a 4-,
5-,
6- or 7-membered, saturated or unsaturated heterocyclic radical which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubsti- tuted or may carry 1 , 2, 3 or 4 groups, which are identical or different and selected from the group consisting of =0, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
R22 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2- C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-
C6-cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci- C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Z1, phenyl-0-Ci-C6-alkyl, phenyl-N(R23)-Ci-Ce-alkyl, phenyl-S(0)n-Ci-C6-alkyl, heterocyclyl-Z1, heterocyclyl- N(R23)-Ci-C6-alkyl, heterocyclyl-O-d-Ce-alkyl, and heterocyclyl-S(0)n-Ci-C6-alkyl, where heterocydyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, heterocydyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of cyano, halogen, nitro, thiocyanato, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C(0)OR23, C(0) N(R23)2,
OR23, N(R23)2, S(0)nR24, S(0)2OR23, S(0)2N(R23)2, and R230-Ci-C6-alkyl, and where heterocydyl bears 0, 1 or 2 oxo groups; is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2- C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl; R24 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, and phenyl;
R25 is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- cycloalkenyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6- alkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy-Ci-C6-alkyl, phenyl-Z1, phenyl-0-Ci-C6-alkyl, phenyl-N(R23)-Ci-C6-alkyl, phenyl-S(0)n-Ci-C6-alkyl, heterocyclyl-Z1, heterocyclyl- N(R23)-Ci-C6-alkyl, heterocyclyl-0-Ci-C6-alkyl, and heterocyclyl-S(0)n-Ci-C6-alkyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle which contains 1 , 2, 3 or 4 heteroatoms as ring members which are selected from the group consisting of O, N and S, where phenyl, heterocyclyl are unsubstituted or substituted by 1 , 2, 3 or 4 groups which are identical or different and selected from the group consisting of cyano, halogen, nitro, thiocyanato, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C(0)OR23, C(0)N(R23)2, OR23, N(R23)2, S(0)nR24, S(0)2OR23, S(0)2N(R23)2, and R230-Ci-C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; k is 0, 1 or 2; n is 0, 1 or 2; and
Rk independently has the meanings of R3c; or a N-oxide or an agriculturally suitable salt thereof.
The compound as claimed in claim 1 , an N-oxide or an agriculturally suitable salt thereof, where Q is Q1.
The compound as claimed in claim 1 , an N-oxide or an agriculturally suitable salt thereof, where Q is Q2.
The compound as claimed in claim 1 , an N-oxide or an agriculturally suitable salt thereof, where Q is Q3.
The compound as claimed in claim 1 , an N-oxide or an agriculturally suitable salt thereof, where Q is Q4.
The compound as claimed in any of claims 1 to 5, an N-oxide or an agriculturally suitable salt thereof, where R1 is selected from the group consisting of halogen, nitro, Ci-Cs-alkyl, Ci-C4-alkoxy-Ci-C4-alkoxy-Z1 and R1b-S(0)k-Z1.
7. The compound as claimed in claim 6, where R1 is halogen.
The compound as claimed in any of claims 1 to 7, or an agriculturally suitable salt thereof, where R2 is Ci-C6-alkyl-S(0)n-Z2 or phenyl-S(0)n-Z2,
wherein the phenyl ring is unsubstituted or substituted by 1 , 2, 3 or 4 groups selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl and Ci-C4-alkoxy, and in particular from the group consisting of halogen and Ci-C4-haloalkyl.
9. The compound as claimed in any of claims 1 to 7, or an agriculturally suitable salt thereof, where R2 is C3-C6-cycloalkyl-S(0)n-Z2, in particular cyclopropyl-S(0)n-Z2.
10. The compound as claimed in any of claims 1 to 9, or an agriculturally suitable salt thereof, where Z2 is unsubstituted Ci-C2-alkanediyl, and is in particular CH2CH2.
1 1 . The compound as claimed in any of claims 1 to 7, or an agriculturally suitable salt thereof, where R2 is heterocyclyl-Z2a, where heterocyclyl is a 5- or 6-membered saturated hetero- cycle which contains one S(0)n group as ring member; and Z2a is a bond or unsubstituted Ci-C2-alkanediyl, in particular a bond or Chb; and specifically a bond.
12. The compound as claimed in any of claims 1 to 1 1 , where in R2 the index n is 0 if R2 is Ci- C6-alkyl-S(0)n-Z2, Ci-C6-haloalkyl-S(0)n-Z2, C3-C6-cycloalkyl-S(0)n-Z2 or heteroaryl-S(0)n- Z2, and is 0, 1 or 2 if R2 is phenyl-S(0)n-Z2.
13. The compound as claimed in any of claims 1 to 12, an N-oxide or an agriculturally suitable salt thereof, where R3 is selected from the group consisting of halogen, nitro, Ci-C6-alkyl, d-Ce-haloalkyl, Ci-C8-haloalkoxy-Z3, and R2b-S(0)k-Z3.
14. The compound as claimed in claim 13, an N-oxide or an agriculturally suitable salt thereof, where R3 is halogen or Ci-C4-alkylsulfonyl and is in particular halogen.
15. The compound as claimed in any of claims 1 to 14, an N-oxide or an agriculturally suitable salt thereof, where R4 is hydrogen.
16. The compound as claimed in any of claims 1 to 15, an N-oxide or an agriculturally suitable salt thereof, where R5 is halogen, in particular F.
17. The compound as claimed in any of claims 1 to 16, an N-oxide or an agriculturally suitable salt thereof, where R6 is selected from the group consisting of Ci-C6-alkyl, Ci-C4-alkoxy- Ci-C4-alkyl, and phenyl; and is in particular Ci-C4-alkyl.
18. A composition comprising at least one compound as claimed in any of claims 1 to 17, an N-oxide or an agriculturally suitable salt thereof, and at least one auxiliary, which is customary for formulating crop protection compounds.
19. The use of a compound as claimed in any of claims 1 to 17, an N-oxide or an agriculturally suitable salt thereof, or of the composition of claim 18 for controlling unwanted vegetation.
20. A method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one compound as claimed in any of claims 1 to 17, an N-oxide or an agriculturally suitable salt thereof, or of the composition of claim 18 to act on plants, their seed and/or their habitat.
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