TREA

BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES II

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Information

  • Patent Application
  • 20210179569
  • Publication Number
    20210179569
  • Date Filed
    May 29, 2018
    5 years ago
  • Date Published
    June 17, 2021
    2 years ago
Information
Abstract
The invention relates to benzamides of formula I,
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 2011/035874 describes N-(1,2,5-oxadiazol-3-yl)benzamides carrying 3 substituents in the 2-, 3- and 4-positions of the phenyl ring and their use as herbicides.


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.


WO2013/017559 describes N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxylic acid amides carrying 3 substituents in the 2-, 3- and 4-positions of the aryl ring and their use as herbicides.


WO2013/124245 describes N-(tetrazol-5-yl)-, N-(triazol-5-yl)- and N-(1,3,4-oxadiazol-2-yl)arylcarboxylic acid amides carrying 1, 2, or 3 substituents in the 2-, 3- and 5-positions of the aryl ring and a nitro group in the 4 position of the aryl ring and their use as herbicides.


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 sufficiently 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,




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    • wherein

    • Q is Q1 or Q2 or Q3 or Q4,







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    • R1 is selected from the group consisting of cyano, halogen, nitro, C1-C8-alkyl, C1-C8-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1, C1-C6-haloalkoxy, R1b—S(O)k—Z1;

    • R2 is R2cR2dNC(O)NR2n—Z2;

    • R3 is selected from the group consisting of hydrogen, cyano, thiocyanato, halogen, hydroxy-Z2, C1-C6-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C10-cycloalkyl-Z2, C3-C6-cycloalkenyl-Z2, C3-C10-cycloalkoxy-Z2, C3-C10-cycloalkyl-C1-C2-alkoxy, where the cyclic groups of the four aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C4-cyanoalkyl, C1-C8-haloalkyl, C2-C8-haloalkenyl, C3-C8-haloalkynyl, C1-C8-alkoxy-Z2, C1-C8-haloalkoxy-Z2, C1-C4-alkoxy-C1-C4-alkoxy-Z2, C1-C4-haloalkoxy-C1-C4-alkoxy-Z2, C2-C8-alkenyloxy-Z2, C2-C8-alkynyloxy-Z2, C2-C8-haloalkenyloxy-Z2, C3-C8-haloalkynyloxy-Z2, R2b—S(O)k—Z2, R2c—C(O)—Z2, R2dO—C(O)—Z2, R2dO—N═CH—Z2, R2eR2fN—C(O)—Z2, R2gR2hN—Z2, R22C(O)O—Z2, R25OC(O)O—Z2, (R22)2NC(O)O—Z2, R25S(O)2O—Z2, R22OS(O)2—Z2, (R22)2NS(O)2—Z2, R25OC(O)N(R22)—Z2, (R22)2NC(O)N(R22)—Z2, (R22)2NS(O)2N(R22)—Z2, (OH)2P(O)—Z2, (C1-C4-alkoxy)2P(O)—Z2, phenyl-Z2a, heterocyclyl-Z2a, 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-Z2a and heterocyclyl-Z2a 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 halogen, C1-C8-alkyl, cyano-Z1, nitro, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C2-C8-alkenyl, C2-C8-alkynyl, C1-C8-haloalkyl, C1-C3-alkylamino, C1-C3-dialkylamino, C1-C3-alkylamino-S(O)k, C1-C3-alkylcarbonyl, C1-C8-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-Z1, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkylthio-Z1, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkoxy, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkoxy-Z1, R1b—S(O)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 hydrogen;

    • R6 is selected from the group consisting of cyano, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups of the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, Rb—S(O)n—C1-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

    • R21 is selected from the group consisting of cyano, halogen, nitro, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-halocycloalkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy, C3-C7-cycloalkoxy and C1-C6-haloalkoxy, or two radicals R21 bound to the same carbon atom together may form a group ═O;

    • Z1, Z2 independently of each other are selected from the group consisting of a covalent bond and C1-C4-alkanediyl;

    • Z2a is selected from the group consisting of a covalent bond, C1-C4-alkanediyl, O—C1-C4-alkanediyl, C1-C4-alkanediyl-O and C1-C4-alkanediyl-O—C1-C4-alkanediyl;

    • Rb, R1b, R2b independently of each other are selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C1-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, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

    • R2c is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylS(O)n—C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, C1-C4-dialkylamino-C1-C4-alkyl, C1-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;

    • R2d is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C1-C4-alkyl-C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylS(O)n—C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, C1-C4-dialkylamino-C1-C4-alkyl, C1-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; or

    • R2c, R2d 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 ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;





R2n is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C1-C6-cyanoalkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl;

    • R2e, R2f independently of each other are selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned 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-C1-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; or
    • R2e, R2f 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 ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
    • R2g is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned 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-C1-C4-alkyl, C1-C4-alkylsulfonyl, C1-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
    • R2h is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, where the C3-C7-cycloalkyl groups in the two aforementioned 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-C1-C4-alkyl, C1-C4-alkylsulfonyl, C1-C4-alkylcarbonyl, a radical C(O)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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; or
    • R2g, R2h 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 ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
    • R22 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-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-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl, phenyl-Z1, phenyl-O—C1-C6-alkyl, phenyl-N(R23)—C1-C6-alkyl, phenyl-S(O)n—C1-C6-alkyl, heterocyclyl-Z1, heterocyclylN(R23)—C1-C6-alkyl, heterocyclyl-O—C1-C6-alkyl, heterocyclyl-S(O)n—C1-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, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C(O)OR23, C(O)N(R23)2, OR23, N(R23)2, S(O)nR24, S(O)2OR23, S(O)2N(R23)2, and R23O—C1-C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups;
    • R23 is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, and phenyl;
    • R24 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, and phenyl;
    • R25 is selected from the group consisting of C1-C6-alkyl, C1-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-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkoxy-C1-C6-alkyl, phenyl-Z1, phenyl-O—C1-C6-alkyl, phenyl-N(R23)—C1-C6-alkyl, phenyl-S(O)n—C1-C6-alkyl, heterocyclyl-Z1, heterocyclyl-N(R23)—C1-C6-alkyl, heterocyclyl-O—C1-C6-alkyl, heterocyclyl-S(O)n—C1-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, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C(O)OR23, C(O)N(R23)2, OR23, N(R23)2, S(O)nR24, S(O)2OR23, S(O)2N(R23)2, and R23O—C1-C6-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups;
    • k is 0, 1 or 2;
    • n is 0, 1 or 2;
    • Rk has the meanings of R2c.


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, 16O by 18O) 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 includes both amorphous and crystalline compounds of formula I, their enantiomers or diastereomers, 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 (NH4+) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.


Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-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 haloalkyl.


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 alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 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 C1-C4-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl (sec-butyl), isobutyl and tert-butyl. Examples for 01-C6-alkyl are, apart those mentioned for C1-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 C1-C10-alkyl are, apart those mentioned for C1-C6-alkyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methyloctyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl, 2-propylpentyl, 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 replaced by one further binding site, thus forming a bivalent moiety.


The term “haloalkyl” as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl 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 (“C1-C8-haloalkyl”), frequently from 1 to 6 carbon atoms (“C1-C6-haloalkyl”), more frequently 1 to 4 carbon atoms (“C1-C4-haloalkyl”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from C1-C4-haloalkyl, more preferably from C1-C2-haloalkyl, more preferably from halomethyl, in particular from C1-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 C1-C2-fluoroalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like. Examples for C1-C2-haloalkyl are, apart those mentioned for C1-C2-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, 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 C1-C4-haloalkyl are, apart those mentioned for C1-C2-haloalkyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl, 4-chlorobutyl and the like.


The term “cycloalkyl” as used herein (and in the cycloalkyl moieties of other groups comprising a cycloalkyl group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms (“C3-C10-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.


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 cycloalkyl group, as defined above, which is bound to the remainder of the molecule via an alkylene group. The term “C3-C7-cycloalkyl-C1-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, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, 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-C8-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”), preferably 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 (“C3-C8-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 mentioned 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 “alkoxy” as used herein denotes in each case a straight-chain or branched alkyl group usually having from 1 to 8 carbon atoms (“C1-C8-alkoxy”), frequently from 1 to 6 carbon atoms (“C1-C6-alkoxy”), preferably 1 to 4 carbon atoms (“C1-C4-alkoxy”), which is bound to the remainder of the molecule via an oxygen atom. C1-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). C1-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-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. C1-C8-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 (“C1-C8-haloalkoxy”), frequently from 1 to 6 carbon atoms (“C1-C6-haloalkoxy”), preferably 1 to 4 carbon atoms (“C1-C4-haloalkoxy”), more preferably 1 to 3 carbon atoms (“C1-C3-haloalkoxy”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms. C1-C2-Haloalkoxy is, for example, OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, 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. C1-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-(CH2Cl)-2-chloroethoxy, 1-(CH2Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C1-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.


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. “C1-C6-alkoxy-C1-C6-alkyl” is a C1-C6-alkyl group, as defined above, in which one hydrogen atom is replaced by a C1-C6-alkoxy group, as defined above. Examples are CH2OCH3, CH2—OC2H5, n-propoxymethyl, CH2—OCH(CH3)2, n-butoxymethyl, (1-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, difluoromethoxymethyl, 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, pentafluoroethoxymethyl, 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 “alkylthio” (also alkylsulfanyl, “alkyl-S” or “alkyl-S(O)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 (“C1-C8-alkylthio”), frequently comprising 1 to 6 carbon atoms (“C1-C6-alkylthio”), preferably 1 to 4 carbon atoms (“C1-C4-alkylthio”), which is attached via a sulfur atom at any position in the alkyl group. C1-C2-Alkylthio is methylthio or ethylthio. C1-C4-Alkylthio is additionally, for example, n-propylthio, 1-methylethylthio (isopropylthio), butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1,1-dimethylethylthio (tert-butylthio). C1-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. C1-C8-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. C1-C2-Haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2Cl, SCHCl2, SCCl3, 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. C1-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, SCF2C2F5, 1-(CH2F)-2-fluoroethylthio, 1-(CH2Cl)-2-chloroethylthio, 1-(CH2Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. C1-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(O)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 example, the term “C1-C2-alkylsulfinyl” refers to a C1-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C4-alkylsulfinyl” refers to a C1-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C1-C6-alkylsulfinyl” refers to a C1-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. C1-C2-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C1-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-ethylbutylsulfinyl, 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(O)k” (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C2-alkylsulfonyl” refers to a C1-C2-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C4-alkylsulfonyl” refers to a C1-C4-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. The term “C1-C6-alkylsulfonyl” refers to a C1-C6-alkyl group, as defined above, attached via a sulfonyl [S(O)2] group. C1-C2-alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C1-C4-alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1-methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1-methylpropylsulfonyl (secbutylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1,1-dimethylethylsulfonyl (tertbutylsulfonyl). C1-C6-alkylsulfonyl is additionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-di methyl propylsulfonyl, 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 “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 (“C1-C4-alkylamino”). Examples of C1-C6-alkylamino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, isobutylamino, tert-butylamino, and the like.


The term “dialkylamino” as used herein denotes in each case a group R*RoN—, wherein R* and Ro, independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms (“di-(C1-C6-alkyl)-amino”), preferably 1 to 4 carbon atoms (“di(C1-C4-alkyl)-amino”). Examples of a di-(C1-C6-alkyl)-amino group are dimethylamino, diethylamino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methylisopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethylisopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and the like.


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═O group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl.


The term “aryl” as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical 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, pyrimidyl and the like.


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 unsaturated heterocycle contains at least one C—C and/or C—N and/or N—N double bond(s). A fully unsaturated heterocycle contains as many conjugated C—C and/or C—N and/or N—N double bonds as allowed by the size(s) of the ring(s). An aromatic monocyclic heterocycle is a fully unsaturated 5- or 6-membered monocyclic heterocycle. 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, tetrahydrothien-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, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-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, hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-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-di hydrothien-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 tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- or tetrahydrotriazin-2-yl and 1,2,4-di- or tetrahydrotriazin-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, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, isochinolinyl, purinyl, 1,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.


If two radicals bound on the same nitrogen atom (for example R2c and R2d or R2e and R2f or R2g and R2h) together with the nitrogen atom, to which they are bound, form a 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 pyrrolidine-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, isothiazolin-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, piperazine-1-yl, morpholin-1-yl, thiomorpholin-1-yl, 1-oxothiomorpholin-1-yl, 1,1-dioxothiomorpholin-1-yl, azepan-1-yl, 1,4-diazepan-1-yl, pyrrolin-1-yl, pyrazolin-1-yl, imidazolin-1-yl, oxazolin-3-yl, isoxazolin-2-yl, thiazolin-3-yl, isothiazolin-1-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]-1H-triazol-1-yl, [1,2,3]-2H-triazol-2-yl, [1,2,4]-1H-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 compounds 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 a first group 1 of embodiments of the invention the variable Q in the compounds of formula I is Q1:




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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:




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According to a second group 2 of embodiments of the invention the variable Q in the compounds of formula I is Q2:




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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:




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According to a third group 2 of embodiments of the invention the variable Q in the compounds of formula I is Q3:




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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 following formula I.C, where the variables R1, R2, R3, R4 and R6 are as defined herein:




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According to a fourth group 4 of embodiments of the invention the variable Q in the compounds of formula I is Q4:




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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:




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Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein R1 is selected from the group consisting of cyano, halogen, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C6-alkoxy, C1-C4-alkoxy-C1-C4-alkoxy-Z1, R1b—S(O)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 C1-C4-alkyl and C1-C4-haloalkyl. In this context Z1 is in particular a covalent bond.


More preferably, R1 is selected from halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-Z1 and R1b—S(O)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 C1-C4-alkyl and C1-C4-haloalkyl. In this context Z1 is in particular a covalent bond.


In particular, R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, with preference given to R1 being selected from the group consisting of halogen and C1-C4-alkyl. Specifically R1 is F, Cl, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3 or CH2OCH2CH2OCH3, and more specifically R1 is F, Cl, Br, I, nitro, CH3, SCH3 or SO2CH3.


Especially, R1 in formulae I, I.A, I.B, I.C and I.Di s CH3 or Cl.


According to the present invention, R2 is R2cR2dNC(O)NR2n—Z2.


A particular group 5 of embodiments according to the invention are compounds of formula I and the agriculturally suitable salts thereof, and likewise the compounds of formulae I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein in R2, Z2 is C1-C4-alkanediyl; preferably, Z2 is —CH2— or —CH2CH2—, i.e. R2 is R2cR2dNC(O)NR2nCH2— or R2cR2dNC(O)NR2nCH2CH2—;


According to another preferred embodiment, Z2 is a covalent bond, i.e. R2 is R2cR2dNC(O)NR2n—.


According to a preferred group 6 of embodiments, Z2 in formulae I, I.A, I.B, I.C and I.D is a covalent bond and R2n is selected from the group consisting of hydrogen and C1-C6-alkyl.


According to an even more group 7 of embodiments, Z2 in formulae I, I.A, I.B, I.C and I.D is a covalent bond and R2n is hydrogen, i.e. R2 is R2cR2dNC(O)NH—.


In the context of R2, and likewise in the context of groups 1, 2, 3, 4, 5, 6, and 7 of embodiments, R2c is preferably selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl, C1-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;


More preferably, R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, C1-C4-haloalkyl, C1-C4-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 C1-C4-alkoxy;


Even more preferably, R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl.


Herein, particularly preferably, R2c is selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-CH3O-phenyl, and phenyl, or R2c is selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2— and CF3CH2—.


In the context of R2, and likewise in the context of groups 1, 2, 3, 4, 5, 6, and 7 of embodiments, R2d is preferably selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-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, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;


more preferably, R2d is selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C2-alkyl and C1-C6-haloalkyl, in particular selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl;


Herein, very particularly preferably, R2d is methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, or CF3CH2—.


In the context of R2, and likewise in the context of groups 1, 2, 3, 4, 5, 6, and 7 of embodiments, the combination of R2c and R2d is preferably as follows:


R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl and C1-C4-haloalkyl;


R2d is selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C2-alkyl and C1-C6-haloalkyl.


In the context of R2, and likewise in the context of groups 1, 2, 3, 4, 5, 6, and 7 of embodiments, the combination of R2c and R2d is even more preferably as follows:


R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl, with particular preference given to R2c being methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, or CF3CH2—; and


R2d is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl and C1-C4-haloalkyl, with particular preference given to R2d being methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, or CF3CH2—.


In the context of R2, and likewise in the context of groups 1 2, 3, 4, 5, 6, and 7 of embodiments, the combination of R2c and R2d is also preferably as follows:


R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl, with particular preference given to R2c being methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, or CF3CH2—; and


R2d is selected from the group consisting of C3-C7-cycloalkyl and C1-C4-haloalkyl, with particular preference given to R2d being cyclopropyl (cPr), CHF2CH2—, or CF3CH2—.


In the context of R2, and likewise in the context of groups 1, 2, 3, 4, 5, 6, and 7 of embodiments, R2c and R2d together with the nitrogen atom, to which they are bound may also 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 ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;


preferably, R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein R3 is selected from the group consisting of hydrogen, cyano, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C2-C4-alkenyloxy, C2-C4-alkynyloxy or R2b—S(O)k, where the variables k and R2b have one of the herein defined meanings; in particular, R3 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, or R2b—S(O)k, where the variables k and R2b have one of the herein defined meanings.


More preferably, R3 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkyl-S(O), C1-C4-haloalkyl-S(O), C1-C4-alkyl-S(O)2, and C1-C4-haloalkyl-S(O)2.


In particular, R3 is selected from the group consisting of hydrogen, halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2, specifically from H, Cl, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3, and more specifically from H, Cl, Br, I, CF3, SCH3, S(O)CH3 and S(O)2CH3. Especially, R3 is selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl, with particular preference given to those compounds, where R3 is selected from the group consisting of H, Cl, Br and CF3, with even more preference given to compounds of the formulae I.A and I.D and the agriculturally acceptable salts thereof, where R3 is selected from the group consisting of H, Cl, Br and CF3.


In special subgroups embodiments 1, 2, 3, 4, 5, 6, 7, R3 in formulae I, I.A, I.B, I.C and I.D is hydrogen. In other special subgroups embodiments 1, 2, 3, 4, 5, 6, 7, R3 in formulae I, I.A, I.B, I.C and I.D is different from hydrogen.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein R4 is selected from the group consisting of cyano, halogen, nitro, C1-C2-alkyl, and C1-C2-haloalkyl. More preferably, R4 is selected from the group consisting of cyano, halogen, nitro, CH3, CHF2, and CF3, in particular from cyano, chlorine, fluorine and CH3. Most preferred compounds according to the invention are compounds of formula I, wherein R4 is chlorine or fluorine.


Preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein R6 is selected from the group consisting of 01-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl. In particular, R6 is selected from the group consisting of C1-C2-alkyl, C1-C2-alkoxy-C1-C2-alkyl, specifically from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2. Especially preferred compounds according to the invention are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, where R6 is CH3.


In this context, the variables R21, Z1, Z2, Z2a, Rb, R1b, R2b, R2c, R2d, R2e, R2f, R2g, R2h, Rk, n and k, independently of each other, preferably have one of the following meanings:


R21 is selected from halogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy and C1-C6-haloalkyloxy, more preferably from halogen, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl and C1-C4-alkoxy.


More preferably R21 is selected from the group consisting of halogen, C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl and C1-C4-alkoxy-C1-C4-alkoxy; in particular from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl and C1-C4-alkoxy-C1-C4-alkoxy; and specifically from Cl, F, Br, methyl, ethyl, methoxy and trifluoromethyl.


Z1, Z2 independently of each other are selected from a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond.


Z2a is selected from a covalent bond, C1-C2-alkanediyl, O—C1-C2-alkanediyl, C1-C2-alkanediyl-O and C1-C2-alkanediyl-O—C1-C2-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyl, O-ethanediyl, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.


Rb, R1b, R2b independently of each other are selected from C1-C6-alkyl, C3-C7-cycloalkyl, C1-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, C1-C4-alkyl, C1-C2-haloalkyl and C1-C2-alkoxy.


More preferably Rb, R1b, R2b independently of each other are selected from the group consisting of C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-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 0, N and S.


In particular, Rb, R1b, R2b independently of each other are selected from C1-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.


R2c, Rk independently of each other are selected from hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-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, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy.


More preferably R2c, Rk independently of each other are selected from hydrogen, C1-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 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, R2c, Rk independently of each other are selected from hydrogen, C1-C4-alkyl, C1-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.


R2d is selected from C1-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl.


More preferably R2d is selected from C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C1-C4-alkoxy-C1-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C3-C6-cycloalkyl.


R2e, R2f independently of each other are selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partially or completely halogenated, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C4-alkoxy-C1-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, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy, or R2e and R2f 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, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy.


More preferably R2e, R2f independently of each other are selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and benzyl, or R2e and R2f 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, C1-C4-alkyl and C1-C4-haloalkyl.


In particular, R2e, R2f independently of each other are selected from hydrogen and C1-C4-alkyl, or R2e and R2f 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.


R2g is selected from hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl and benzyl.


More preferably R2g is selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, C1-C4-alkoxy-C1-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl.


R2h is selected from hydrogen, C1-C6-alkyl, C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, phenyl, benzyl and a radical C(═O)—Rk, where Rk is H, C1-C4-alkyl, C1-C4-haloalkyl or phenyl.


More preferably R2h is selected from hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, benzyl, C1-C4-alkoxy-C1-C4-alkyl and C3-C7-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, benzyl and C3-C6-cycloalkyl; or R2g and R2h 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 ═O, halogen, C1-C4-alkyl and C1-C4-haloalkyl and C1-C4-alkoxy;


more preferably R2g and R2h 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, C1-C4-alkyl and C1-C4-haloalkyl;


and in particular, R2g and R2h 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.


Particularly preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein the variables R1 and R3 have the following meanings:


R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-Z1 and R1b—S(O)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 C1-C4-alkyl and C1-C4-haloalkyl with preference given to R1 being selected from the group consisting of halogen and C1-C4-alkyl. In this context Z1 is in particular a covalent bond. In particular, R1 is selected from F, Cl, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3, and CH2OCH2CH2OCH3 with most preference given to CH3 and Cl; and


R3 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkyl-S(O), C1-C4-haloalkyl-S(O), C1-C4-alkyl-S(O)2, and C1-C4-haloalkyl-S(O)2 with preference given to R3 being selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl.


In particular, R3 is selected from H, Cl, F, Br, I, CH, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3 with most preference given to H, Cl, Br and CF3.


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, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl, with preference given to R1 being selected from the group consisting of halogen and C1-C4-alkyl; in particular R1 is selected from the group consisting of F, Cl, Br, I, nitro, CH3, SCH3 and SO2CH3 with most preference given to CH3 and Cl; and


R3 is selected from the group consisting of hydrogen, halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 with preference given to R3 being selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl, most particular from H, Cl, Br, I, CF3, SCH3, S(O)CH3 and S(O)2CH3 with most preference given to H, Cl, Br and CF3.


Especially preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4 and R6 have the following meanings:


R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-Z1 and R1b—S(O)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 C1-C4-alkyl and C1-C4-haloalkyl with preference given to R1 being selected from the group consisting of halogen and C1-C4-alkyl. In this context Z1 is in particular a covalent bond; specifically R1 is selected from F, Cl, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3, and CH2OCH2CH2OCH3 with most preference given to CH3 and Cl;


R2 is R2cR2dNC(O)NR2n—;


R2n is hydrogen;


R2c is selected from C1-C4-alkyl, C3-C7-cycloalkyl, C1-C4-haloalkyl, C1-C4-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 C1-C4-alkoxy; specifically, R2c is selected from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-CH3O-phenyl, or phenyl;


R2d is selected from C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl, preferably from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—; or


R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl;


R3 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkyl-S(O), C1-C4-haloalkyl-S(O), C1-C4-alkyl-S(O)2, and C1-C4-haloalkyl-S(O)2, with preference given to R3 being selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl, in particular from H, Cl, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3 with most preference given to H, Cl, Br and CF3;


R4 is selected from the group consisting of cyano, halogen, nitro, C1-C2-alkyl, and C1-C2-haloalkyl with most preference given to F and Cl;


R6 is selected from the group consisting of C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2 with most preference given to CH3.


Especially preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4 and R6 have the following meanings:


R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-Z1 and R1b—S(O)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 C1-C4-alkyl and C1-C4-haloalkyl. In this context Z1 is in particular a covalent bond with preference given to R1 being selected from the group consisting of halogen and C1-C4-alkyl; specifically R1 is selected from F, Cl, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3, and CH2OCH2CH2OCH3 with most preference given to CH3 and Cl;


R2 is R2nR2dNC(O)NR2n—;


R2n is C1-C6-alkyl, preferably methyl or ethyl;


R2c is selected from C1-C4-alkyl, C3-C7-cycloalkyl, C1-C4-haloalkyl, C1-C4-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 C1-C4-alkoxy; specifically, R2n is selected from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-CH3O-phenyl, or phenyl;


R2d is selected from C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl, preferably from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—; or


R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl;


R3 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkyl-S(O), C1-C4-haloalkyl-S(O), C1-C4-alkyl-S(O)2, and C1-C4-haloalkyl-S(O)2 with preference given to R3 being selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl, in particular from H, Cl, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3 with most preference given to H, Cl, Br and CF3;


R4 is selected from the group consisting of cyano, halogen, nitro, C1-C2-alkyl, and C1-C2-haloalkyl with most preference given to F and Cl;


R6 is selected from the group consisting of C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2 with most preference given to CH3.


Especially preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4 and R6 have the following meanings:


R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl with preference given to R1 being selected from the group consisting of halogen and C1-C4-alkyl; specifically R1 is F, Cl, Br, I, nitro, CH3, SCH3 or SO2CH3 with most preference given to CH3 and Cl;


R2 is R2cR2dNC(O)NR2n—;


R2n is hydrogen;


R2c is selected from C1-C4-alkyl, C3-C7-cycloalkyl, C1-C4-haloalkyl, C1-C4-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 C1-C4-alkoxy; specifically, R2c is selected from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-CH3O-phenyl, or phenyl;


R2d is selected from C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl, preferably from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—; or


R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl;


R3 is selected from the group consisting of hydrogen, halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 with preference given to R3 being selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl, and more specifically from H, Cl, Br, I, CF3, SCH3, S(O)CH3 and S(O)2CH3 with most preference given to H, Cl, Br and CF3;


R4 is selected from the group consisting of cyano, halogen, nitro, CH3, CHF2, and CF3 with most preference given to F and Cl.


R6 is selected from the group consisting of C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2 with most preference given to CH3.


Especially preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4 and R6 have the following meanings:


R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl with preference given to R1 being selected from the group consisting of halogen and C1-C4-alkyl; specifically R1 is F, Cl, Br, I, nitro, CH3, SCH3 or SO2CH3 with most preference given to CH3 and 01;


R2 is R2cR2dNC(O)NR2n—;


R2n is C1-C6-alkyl, preferably methyl or ethyl;


R2c is selected from C1-C4-alkyl, C3-C7-cycloalkyl, C1-C4-haloalkyl, C1-C4-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 C1-C4-alkoxy; specifically, R2c is selected from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O, 4-Cl-phenyl, 4-CH3O-phenyl, or phenyl;


R2d is selected from C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl, preferably from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—; or


R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl;


R3 is selected from the group consisting of hydrogen, halogen, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 with preference given to R3 being selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl, and more specifically from H, Cl, Br, I, CF3, SCH3, S(O)CH3 and S(O)2CH3 with most preference given to H, Cl, Br and CF3;


R4 is selected from the group consisting of cyano, halogen, nitro, CH3, CHF2, and CF3 with most preference given to F and Cl.


R6 is selected from the group consisting of C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2 with most preference given to CH3.


Especially preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4 and R6 have the following meanings:


R1 is F, Cl, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3, and CH2OCH2CH2OCH3 with most preference given to CH3 and Cl;


R2 is R2cR2dNC(O)NH—;


R2c is selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, 4-Cl-phenyl, 4-CH3O-phenyl, and phenyl;


R2d is selected from the group consisting of ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—; or


R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl;


R3 is selected from the group consisting of H, Cl, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3 with most preference given to H, Cl, Br and CF3;


R4 is Cl or F;


R6 is selected from the group consisting of CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2 with most preference given to CH3.


Especially preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4 and R6 have the following meanings:


R1 is F, Cl, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3, and CH2OCH2CH2OCH3 with most preference given to H, Cl, Br and CF3;


R2 is R2cR2dNC(O)NR2n—;


R2n is C1-C6-alkyl, preferably methyl or ethyl;


R2c is selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-CH3O-phenyl, and phenyl;


R2d is selected from from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—; or


R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl;


R3 is selected from the group consisting of H, Cl, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3 with most preference given to H, Cl, Br and CF3;


R4 is chlorine or fluorine;


R6 is selected from the group consisting of CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2 with most preference given to CH3.


Especially preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4 and R6 have the following meanings:

    • R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-Z1 and R1b—S(O)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 C1-C4-alkyl and C1-C4-haloalkyl with preference given to R1 being selected from the group consisting of halogen and C1-C4-alkyl. In this context Z1 is in particular a covalent bond; specifically R1 is selected from F, Cl, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3, and CH2OCH2CH2OCH3 with most preference given to CH3 and Cl;
    • R2 is R2cR2dNC(O)NR2n—Z2;
    • Z2 is C1-C4-alkanediyl, preferably —CH2— or —CH2CH2—;
    • R2n is selected from hydrogen and C1-C6-alkyl, preferably from hydrogen, methyl and ethyl;
    • R2c is selected from C1-C4-alkyl, C3-C7-cycloalkyl, C1-C4-haloalkyl, C1-C4-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 C1-C4-alkoxy; specifically, R2c is selected from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-CH3O-phenyl, or phenyl;
    • R2d is selected from C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl, preferably from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—; or
    • R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl;
    • R3 is selected from the group consisting of hydrogen, halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkyl-S(O), C1-C4-haloalkyl-S(O), C1-C4-alkyl-S(O)2, and C1-C4-haloalkyl-S(O)2 with preference given to R3 being selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl; R3 is in particular selected from the group consisting of H, Cl, F, Br, I, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3 with most preference given to H, Cl, Br and CF3;
    • R4 is selected from the group consisting of cyano, halogen, nitro, C1-C2-alkyl, and C1-C2-haloalkyl with most preference given to F and Cl;
    • R6 is selected from the group consisting of C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2 with most preference given to CH3.


Especially preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4 and R6 have the following meanings:


R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio, C1-C4-haloalkylthio and C1-C4-alkylsulfonyl with preference given to R1 being selected from the group consisting of halogen and C1-C4-alkyl; specifically R1 is F, Cl, Br, I, nitro, CH3, SCH3 or SO2CH3 with most preference given to CH3 and Cl;

    • R2 is R2cR2dNC(O)NR2n—Z2;
    • Z2 is C1-C4-alkanediyl, preferably —CH2— or —CH2CH2—;
    • R2n is selected from hydrogen and C1-C6-alkyl, preferably from hydrogen, methyl and ethyl;


R2c is selected from C1-C4-alkyl, C3-C7-cycloalkyl, C1-C4-haloalkyl, C1-C4-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 C1-C4-alkoxy; specifically, R2c is selected from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-CH3O-phenyl, or phenyl;

    • R2d is selected from C1-C4-alkyl, C3-C7-cycloalkyl, and C1-C4-haloalkyl, preferably from methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—; or
    • R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl;
    • R3 is selected from the group consisting of hydrogen, halogen, nitro, C1-C2-alkyl, C1-C2-haloalkyl, C1-C2-haloalkoxy, C1-C2-alkylthio, C1-C2-haloalkylthio, C1-C2-alkyl-S(O), C1-C2-haloalkyl-S(O), C1-C2-alkyl-S(O)2 and C1-C2-haloalkyl-S(O)2 with preference given to R3 being selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl, and more specifically from Cl, Br, I, CF3, SCH3, S(O)CH3 and S(O)2CH3 with most preference given to H, Cl, Br and CF3;
    • R4 is selected from the group consisting of cyano, halogen, nitro, CH3, CHF2, and CF3 with most preference given to F and Cl;
    • R6 is selected from the group consisting of C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl, in particular from CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2 with most preference given to CH3.


Especially preferred are compounds of formulae I, I.A, I.B, I.C and I.D and the agriculturally suitable salts thereof, wherein Q is Q1, Q2, Q3 or Q4 and the variables R1, R2, R3, R4 and R6 have the following meanings:


R1 is F, Cl, Br, I, nitro, CH3, SCH3, SCF3, SO2CH3, and CH2OCH2CH2OCH3 with most preference given to CH3 and Cl;

    • R2 is R2cR2dNC(O)NR2n—Z2;
    • Z2 is C1-C4-alkanediyl, preferably —CH2— or —CH2CH2—;
    • R2n is selected from hydrogen and C1-C6-alkyl, preferably from hydrogen, methyl and ethyl;
    • R2c is selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—, CH3O—, 4-Cl-phenyl, 4-CH3O-phenyl, and phenyl;
    • R2d is selected from from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—; or
    • R2c and R2d 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 C1-C4-alkyl and C1-C4-haloalkyl, preferably from methyl, ethyl and trifluoromethyl;
    • R3 is selected from the group consisting of Cl, F, Br, I, NO2, CH3, CF3, CHF2, OCF3, OCHF2, SCH3, SCF3, SCHF2, S(O)CH3, S(O)CH2CH3, S(O)2CH3 and S(O)2CH2CH3 with most preference given to H, Cl, Br and CF3;
    • R4 is chlorine or fluorine;
    • R6 is selected from the group consisting of CH3, CH3CH2, CH3OCH2CH2 and CH3OCH2 with most preference given to CH3.


Particularly preferred are compounds of the formulae I, I.A, I.B, I.C, I.D and the agriculturally suitable salts thereof, where

    • R1 is selected from the group consisting of halogen and C1-C4-alkyl,
    • R2 is R2cR2dNC(O)NH—;
    • R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl and C1-C4-haloalkyl,
    • R2d is selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C2-alkyl and C1-C6-haloalkyl,
    • R3 is selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl.
    • R4 is selected from the group consisting of fluorine and chlorine.


Even more preferred are compounds of the formulae I, I.A, I.B, I.C, I.D and the agriculturally suitable salts thereof, where

    • R1 is selected from the group consisting of CH3 and Cl,
    • R2 is R2cR2dNC(O)NH—;
    • R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl and C1-C4-haloalkyl,
    • R2d is selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C2-alkyl and C1-C6-haloalkyl,
    • R3 is selected from the group consisting of H, Cl, Br and CF3.
    • R4 is selected from the group consisting of fluorine and chlorine.


Especially preferred are compounds of the formulae I, I.A, I.B, I.C, I.D and the agriculturally suitable salts thereof, where

    • R1 is selected from the group consisting of CH3 and Cl,
    • R2 is R2cR2dNC(O)NH—;
    • R2c is selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—,
    • R2d is selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—,
    • R3 is selected from the group consisting of H, Cl, Br and CF3.
    • R4 is selected from the group consisting of fluorine and chlorine.


Particularly preferred are compounds of the formulae I.A.1 and I.D.1 and the agriculturally suitable salts thereof,




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where


R1 is selected from the group consisting of halogen and C1-C4-alkyl,


R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl and C1-C4-haloalkyl,

    • R2d is selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C2-alkyl and C1-C6-haloalkyl,
    • R3 is selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl.
    • R4 is selected from the group consisting of fluorine and chlorine.


Even more preferred are compounds of the formulae I.A.1 and I.D.1 and the agriculturally suitable salts thereof, where R1 is selected from the group consisting of CH3 and Cl,

    • R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl and C1-C4-haloalkyl,
    • R2d is selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C2-alkyl and C1-C6-haloalkyl,
    • R3 is selected from the group consisting of H, Cl, Br and CF3.
    • R4 is selected from the group consisting of fluorine and chlorine.


Especially preferred are compounds of the formulae I.A.1 and I.D.1 and the agriculturally suitable salts thereof, where


R1 is selected from the group consisting of CH3 and Cl,

    • R2c is selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, CF3CH2—,
    • R2d is selected from the group consisting of methyl, ethyl, isopropyl (iPr), cyclopropyl (cPr), CHF2CH2—, and CF3CH2—,
    • R3 is selected from the group consisting of H, Cl, Br and CF3.
    • R4 is selected from the group consisting of fluorine and chlorine.


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, wherein Q is Q1, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 1 Compounds of formula I (I.A.I.1-I.A.I.686) in which the combination of R1, R2c, R2d, and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.II, wherein Q is Q1, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 2 Compounds of formula I (I.A.II.1-I.A.II.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.III, wherein Q is Q1, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 3 Compounds of formula I (I.A.III.1-I.A.III.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.IV, wherein Q is Q1, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 4 Compounds of formula I (I.A.IV.1-I.A.IV.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.V, wherein Q is Q1, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 5 Compounds of formula I (I.A.V.1-I.A.V.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.VI, wherein Q is Q1, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 6 Compounds of formula I (I.A.VI.1-I.A.VI.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.VII, wherein Q is Q1, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 7 Compounds of formula I (I.A.VII.1-I.A.VII.686) in which the combination of R1, R2c, R2d, and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.VIII, wherein Q is Q1, R4 is Fl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 8 Compounds of formula I (I.A.VIII.1-I.A.VII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.IX, wherein Q is Q1, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 9 Compounds of formula I (I.A.IX.1-I.A.IX.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.X, wherein Q is Q1, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 10 Compounds of formula I (I.A.X.1-I.A.X.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.XI, wherein Q is Q1, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 11 Compounds of formula I (I.A.XI.1-I.A.XI.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.A.XII, wherein Q is Q1, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 12 Compounds of formula I (I.A.XII.1-I.A.XII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.I, wherein Q is Q2, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 13 Compounds of formula I (I.B.I.1-I.B.I.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.II, wherein Q is Q2, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 14 Compounds of formula I (I.B.II.1-I.B.II.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.II, wherein Q is Q2, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 15 Compounds of formula I (I.B.III.1-I.B.III.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.IV, wherein Q is Q2, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 16 Compounds of formula I (I.B.IV.1-I.B.IV.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.V, wherein Q is Q2, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 17 Compounds of formula I (I.B.V.1-I.B.V.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.VI, wherein Q is Q2, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 18 Compounds of formula I (I.B.VI.1-I.B.VI.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.VII, wherein Q is Q2, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 19 Compounds of formula I (I.B.VII.1-I.B.VII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.VIII, wherein Q is Q2, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 20 Compounds of formula I (I.B.VIII.1-I.B.VIII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.IX, wherein Q is Q2, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 21 Compounds of formula I (I.B.IX.1-I.B.IX.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.X, wherein Q is Q2, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 22 Compounds of formula I (I.B.X.1-I.B.X.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.XI, wherein Q is Q2, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 23 Compounds of formula I (I.B.XI.1-I.B.XI.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.B.XII, wherein Q is Q2, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 24 Compounds of formula I (I.B.XII.1-I.B.XII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.I, wherein Q is Q3, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and Renin R2 is H:




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Table 25 Compounds of formula I (I.C.I.1-I.C.I.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.II, wherein Q is Q3, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and Renin R2 is H:




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Table 26 Compounds of formula I (I.C.II.1-I.C.II.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.III, wherein Q is Q3, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 27 Compounds of formula I (I.C.III.1-I.C.III.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.IV, wherein Q is Q3, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 28 Compounds of formula I (I.C.IV.1-I.C.IV.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.V, wherein Q is Q3, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 29 Compounds of formula I (I.C.V.1-I.C.V.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.VI, wherein Q is Q3, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 30 Compounds of formula I (I.C.VI.1-I.C.VI.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.VII, wherein Q is Q3, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 31 Compounds of formula I (I.C.VII.1-I.C.VII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.VIII, wherein Q is Q3, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 32 Compounds of formula I (I.C.VII.1-I.C.VIII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.IX, wherein Q is Q3, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 33 Compounds of formula I (I.C.IX.1-I.C.IX.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.X, wherein Q is Q3, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 34 Compounds of formula I (I.C.X.1-I.C.X.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.XI, wherein Q is Q3, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 35 Compounds of formula I (I.C.XI.1-I.C.XI.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.C.XII, wherein Q is Q3, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 36 Compounds of formula I (I.C.XII.1-I.C.XII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.1, wherein Q is Q4, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 37 Compounds of formula I (I.D.I.1-I.D.I.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.II, wherein Q is Q4, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 38 Compounds of formula I (I.D.II.1-I.D.II.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.III, wherein Q is Q4, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 39 Compounds of formula I (I.D.III.1-I.D.III.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.IV, wherein Q is Q4, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 40 Compounds of formula I (I.D.IV.1-I.D.IV.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.V, wherein Q is Q4, R4 is Cl, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 41 Compounds of formula I (I.D.V.1-I.D.V.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.VI, wherein Q is Q4, R4 is Cl, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 42 Compounds of formula I (I.D.VI.1-I.D.VI.686) in which the combination of R1, R2c, R2d and R4 for a compound corresponds in each case to one row of Table A;


Compounds I.D.VII, wherein Q is Q4, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 43 Compounds of formula I (I.D.VII.1-I.D.VII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.VIII, wherein Q is Q4, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is H:




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Table 44 Compounds of formula I (I.D.VIII.1-I.D.VIII.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.IX, wherein Q is Q4, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 45 Compounds of formula I (I.D.IX.1-I.D.IX.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.X, wherein Q is Q4, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is methyl:




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Table 46 Compounds of formula I (I.D.X.1-I.D.X.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.XI, wherein Q is Q4, R4 is F, R6 is methyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 47 Compounds of formula I (I.D.XI.1-I.D.XI.686) in which the combination of R1, R2c, R2d and R3 for a compound corresponds in each case to one row of Table A;


Compounds I.D.XII, wherein Q is Q4, R4 is F, R6 is ethyl, Z2 in R2 is a covalent bond and R2n in R2 is ethyl:




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Table 48 Compounds of formula I (I.D.XII.1-I.D.XII.686) in which the combination of R1, R2c, R2d and R4 for a compound corresponds in each case to one row of Table A;














TABLE A







R1
R2c
R2d
R3





















1.
Cl
CH3
CH3
Cl



2.
Cl
CH3
CH3
Br



3.
Cl
CH3
CH3
I



4.
Cl
CH3
CH3
CF3



5.
Cl
CH3
CH3
CH3S(O)



6.
Cl
CH3
CH3
CH3S(O)2



7.
Cl
CH3
CH3
H



8.
Cl
CH3
CH3CH2
Cl



9.
Cl
CH3
CH3CH2
Br



10.
Cl
CH3
CH3CH2
I



11.
Cl
CH3
CH3CH2
CF3



12.
Cl
CH3
CH3CH2
CH3S(O)



13.
Cl
CH3
CH3CH2
CH3S(O)2



14.
Cl
CH3
CH3CH2
H



15.
Cl
CH3
iPr
Cl



16.
Cl
CH3
iPr
Br



17.
Cl
CH3
iPr
I



18.
Cl
CH3
iPr
CF3



19.
Cl
CH3
iPr
CH3S(O)



20.
Cl
CH3
iPr
CH3S(O)2



21.
Cl
CH3
iPr
H



22.
Cl
CH3
cPr
Cl



23.
Cl
CH3
cPr
Br



24.
Cl
CH3
cPr
I



25.
Cl
CH3
cPr
CF3



26.
Cl
CH3
cPr
CH3S(O)



27.
Cl
CH3
cPr
CH3S(O)2



28.
Cl
CH3
cPr
H



29.
Cl
CH3
CHF2CH2
Cl



30.
Cl
CH3
CHF2CH2
Br



31.
Cl
CH3
CHF2CH2
I



32.
Cl
CH3
CHF2CH2
CF3



33.
Cl
CH3
CHF2CH2
CH3S(O)



34.
Cl
CH3
CHF2CH2
CH3S(O)2



35.
Cl
CH3
CHF2CH2
H



36.
Cl
CH3
CF3CH2
Cl



37.
Cl
CH3
CF3CH2
Br



38.
Cl
CH3
CF3CH2
I



39.
Cl
CH3
CF3CH2
CF3



40.
Cl
CH3
CF3CH2
CH3S(O)



41.
Cl
CH3
CF3CH2
CH3S(O)2



42.
Cl
CH3
CF3CH2
H



43.
Cl
CH3CH2
CH3CH2
Cl



44.
Cl
CH3CH2
CH3CH2
Br



45.
Cl
CH3CH2
CH3CH2
I



46.
Cl
CH3CH2
CH3CH2
CF3



47.
Cl
CH3CH2
CH3CH2
CH3S(O)



48.
Cl
CH3CH2
CH3CH2
CH3S(O)2



49.
Cl
CH3CH2
CH3CH2
H



50.
Cl
CH3CH2
iPr
Cl



51.
Cl
CH3CH2
iPr
Br



52.
Cl
CH3CH2
iPr
I



53.
Cl
CH3CH2
iPr
CF3



54.
Cl
CH3CH2
iPr
CH3S(O)



55.
Cl
CH3CH2
iPr
CH3S(O)2



56.
Cl
CH3CH2
iPr
H



57.
Cl
CH3CH2
cPr
Cl



58.
Cl
CH3CH2
cPr
Br



59.
Cl
CH3CH2
cPr
I



60.
Cl
CH3CH2
cPr
CF3



61.
Cl
CH3CH2
cPr
CH3S(O)



62.
Cl
CH3CH2
cPr
CH3S(O)2



63.
Cl
CH3CH2
cPr
H



64.
Cl
CH3CH2
CHF2CH2
Cl



65.
Cl
CH3CH2
CHF2CH2
Br



66.
Cl
CH3CH2
CHF2CH2
I



67.
Cl
CH3CH2
CHF2CH2
CF3



68.
Cl
CH3CH2
CHF2CH2
CH3S(O)



69.
Cl
CH3CH2
CHF2CH2
CH3S(O)2



70.
Cl
CH3CH2
CHF2CH2
H



71.
Cl
CH3CH2
CF3CH2
Cl



72.
Cl
CH3CH2
CF3CH2
Br



73.
Cl
CH3CH2
CF3CH2
I



74.
Cl
CH3CH2
CF3CH2
CF3



75.
Cl
CH3CH2
CF3CH2
CH3S(O)



76.
Cl
CH3CH2
CF3CH2
CH3S(O)2



77.
Cl
CH3CH2
CF3CH2
H



78.
Cl
iPr
iPr
Cl



79.
Cl
iPr
iPr
Br



80.
Cl
iPr
iPr
I



81.
Cl
iPr
iPr
CF3



82.
Cl
iPr
iPr
CH3S(O)



83.
Cl
iPr
iPr
CH3S(O)2



84.
Cl
iPr
iPr
H



85.
Cl
iPr
cPr
Cl



86.
Cl
iPr
cPr
Br



87.
Cl
iPr
cPr
I



88.
Cl
iPr
cPr
CF3



89.
Cl
iPr
cPr
CH3S(O)



90.
Cl
iPr
cPr
CH3S(O)2



91.
Cl
iPr
cPr
H



92.
Cl
iPr
CHF2CH2
Cl



93.
Cl
iPr
CHF2CH2
Br



94.
Cl
iPr
CHF2CH2
I



95.
Cl
iPr
CHF2CH2
CF3



96.
Cl
iPr
CHF2CH2
CH3S(O)



97.
Cl
iPr
CHF2CH2
CH3S(O)2



98.
Cl
iPr
CHF2CH2
H



99.
Cl
iPr
CF3CH2
Cl



100.
Cl
iPr
CF3CH2
Br



101.
Cl
iPr
CF3CH2
I



102.
Cl
iPr
CF3CH2
CF3



103.
Cl
iPr
CF3CH2
CH3S(O)



104.
Cl
iPr
CF3CH2
CH3S(O)2



105.
Cl
iPr
CF3CH2
H



106.
Cl
cPr
cPr
Cl



107.
Cl
cPr
cPr
Br



108.
Cl
cPr
cPr
I



109.
Cl
cPr
cPr
CF3



110.
Cl
cPr
cPr
CH3S(O)



111.
Cl
cPr
cPr
CH3S(O)2



112.
Cl
cPr
cPr
H



113.
Cl
cPr
CHF2CH2
Cl



114.
Cl
cPr
CHF2CH2
Br



115.
Cl
cPr
CHF2CH2
I



116.
Cl
cPr
CHF2CH2
CF3



117.
Cl
cPr
CHF2CH2
CH3S(O)



118.
Cl
cPr
CHF2CH2
CH3S(O)2



119.
Cl
cPr
CHF2CH2
H



120.
Cl
cPr
CF3CH2
Cl



121.
Cl
cPr
CF3CH2
Br



122.
Cl
cPr
CF3CH2
I



123.
Cl
cPr
CF3CH2
CF3



124.
Cl
cPr
CF3CH2
CH3S(O)



125.
Cl
cPr
CF3CH2
CH3S(O)2



126.
Cl
cPr
CF3CH2
H



127.
Cl
CHF2CH2
CHF2CH2
Cl



128.
Cl
CHF2CH2
CHF2CH2
Br



129.
Cl
CHF2CH2
CHF2CH2
I



130.
Cl
CHF2CH2
CHF2CH2
CF3



131.
Cl
CHF2CH2
CHF2CH2
CH3S(O)



132.
Cl
CHF2CH2
CHF2CH2
CH3S(O)2



133.
Cl
CHF2CH2
CHF2CH2
H



134.
Cl
CHF2CH2
CF3CH2
Cl



135.
Cl
CHF2CH2
CF3CH2
Br



136.
Cl
CHF2CH2
CF3CH2
I



137.
Cl
CHF2CH2
CF3CH2
CF3



138.
Cl
CHF2CH2
CF3CH2
CH3S(O)



139.
Cl
CHF2CH2
CF3CH2
CH3S(O)2



140.
Cl
CHF2CH2
CF3CH2
H



141.
Cl
CF3CH2
CF3CH2
Cl



142.
Cl
CF3CH2
CF3CH2
Br



143.
Cl
CF3CH2
CF3CH2
I



144.
Cl
CF3CH2
CF3CH2
CF3



145.
Cl
CF3CH2
CF3CH2
CH3S(O)



146.
Cl
CF3CH2
CF3CH2
CH3S(O)2



147.
Cl
CF3CH2
CF3CH2
H



148.
Cl
CH3O
CH3
Cl



149.
Cl
CH3O
CH3
Br



150.
Cl
CH3O
CH3
I



151.
Cl
CH3O
CH3
CF3



152.
Cl
CH3O
CH3
CH3S(O)



153.
Cl
CH3O
CH3
CH3S(O)2



154.
Cl
CH3O
CH3
H



155.
Cl
CH3O
CH3CH2
Cl



156.
Cl
CH3O
CH3CH2
Br



157.
Cl
CH3O
CH3CH2
I



158.
Cl
CH3O
CH3CH2
CF3



159.
Cl
CH3O
CH3CH2
CH3S(O)



160.
Cl
CH3O
CH3CH2
CH3S(O)2



161.
Cl
CH3O
CH3CH2
H



162.
Cl
CH3O
iPr
Cl



163.
Cl
CH3O
iPr
Br



164.
Cl
CH3O
iPr
I



165.
Cl
CH3O
iPr
CF3



166.
Cl
CH3O
iPr
CH3S(O)



167.
Cl
CH3O
iPr
CH3S(O)2



168.
Cl
CH3O
iPr
H



169.
Cl
CH3O
cPr
Cl



170.
Cl
CH3O
cPr
Br



171.
Cl
CH3O
cPr
I



172.
Cl
CH3O
cPr
CF3



173.
Cl
CH3O
cPr
CH3S(O)



174.
Cl
CH3O
cPr
CH3S(O)2



175.
Cl
CH3O
cPr
H



176.
Cl
CH3O
CHF2CH2
Cl



177.
Cl
CH3O
CHF2CH2
Br



178.
Cl
CH3O
CHF2CH2
I



179.
Cl
CH3O
CHF2CH2
CF3



180.
Cl
CH3O
CHF2CH2
CH3S(O)



181.
Cl
CH3O
CHF2CH2
CH3S(O)2



182.
Cl
CH3O
CHF2CH2
H



183.
Cl
CH3O
CF3CH2
Cl



184.
Cl
CH3O
CF3CH2
Br



185.
Cl
CH3O
CF3CH2
I



186.
Cl
CH3O
CF3CH2
CF3



187.
Cl
CH3O
CF3CH2
CH3S(O)



188.
Cl
CH3O
CF3CH2
CH3S(O)2



189.
Cl
CH3O
CF3CH2
H



190.
Cl
Ph
CH3
Cl



191.
Cl
Ph
CH3
Br



192.
Cl
Ph
CH3
I



193.
Cl
Ph
CH3
CF3



194.
Cl
Ph
CH3
CH3S(O)



195.
Cl
Ph
CH3
CH3S(O)2



196.
Cl
Ph
CH3
H



197.
Cl
Ph
CH3CH2
Cl



198.
Cl
Ph
CH3CH2
Br



199.
Cl
Ph
CH3CH2
I



200.
Cl
Ph
CH3CH2
CF3



201.
Cl
Ph
CH3CH2
CH3S(O)



202.
Cl
Ph
CH3CH2
CH3S(O)2



203.
Cl
Ph
CH3CH2
H



204.
Cl
Ph
iPr
Cl



205.
Cl
Ph
iPr
Br



206.
Cl
Ph
iPr
I



207.
Cl
Ph
iPr
CF3



208.
Cl
Ph
iPr
CH3S(O)



209.
Cl
Ph
iPr
CH3S(O)2



210.
Cl
Ph
iPr
H



211.
Cl
Ph
cPr
Cl



212.
Cl
Ph
cPr
Br



213.
Cl
Ph
cPr
I



214.
Cl
Ph
cPr
CF3



215.
Cl
Ph
cPr
CH3S(O)



216.
Cl
Ph
cPr
CH3S(O)2



217.
Cl
Ph
cPr
H



218.
Cl
Ph
CHF2CH2
Cl



219.
Cl
Ph
CHF2CH2
Br



220.
Cl
Ph
CHF2CH2
I



221.
Cl
Ph
CHF2CH2
CF3



222.
Cl
Ph
CHF2CH2
CH3S(O)



223.
Cl
Ph
CHF2CH2
CH3S(O)2



224.
Cl
Ph
CHF2CH2
H



225.
Cl
Ph
CF3CH2
Cl



226.
Cl
Ph
CF3CH2
Br



227.
Cl
Ph
CF3CH2
I



228.
Cl
Ph
CF3CH2
CF3



229.
Cl
Ph
CF3CH2
CH3S(O)



230.
Cl
Ph
CF3CH2
CH3S(O)2



231.
Cl
Ph
CF3CH2
H



232.
Cl
4-Cl-Ph
CH3
Cl



233.
Cl
4-Cl-Ph
CH3
Br



234.
Cl
4-Cl-Ph
CH3
I



235.
Cl
4-Cl-Ph
CH3
CF3



236.
Cl
4-Cl-Ph
CH3
CH3S(O)



237.
Cl
4-Cl-Ph
CH3
CH3S(O)2



238.
Cl
4-Cl-Ph
CH3
H



239.
Cl
4-Cl-Ph
CH3CH2
Cl



240.
Cl
4-Cl-Ph
CH3CH2
Br



241.
Cl
4-Cl-Ph
CH3CH2
I



242.
Cl
4-Cl-Ph
CH3CH2
CF3



243.
Cl
4-Cl-Ph
CH3CH2
CH3S(O)



244.
Cl
4-Cl-Ph
CH3CH2
CH3S(O)2



245.
Cl
4-Cl-Ph
CH3CH2
H



246.
Cl
4-Cl-Ph
iPr
Cl



247.
Cl
4-Cl-Ph
iPr
Br



248.
Cl
4-Cl-Ph
iPr
I



249.
Cl
4-Cl-Ph
iPr
CF3



250.
Cl
4-Cl-Ph
iPr
CH3S(O)



251.
Cl
4-Cl-Ph
iPr
CH3S(O)2



252.
Cl
4-Cl-Ph
iPr
H



253.
Cl
4-Cl-Ph
cPr
Cl



254.
Cl
4-Cl-Ph
cPr
Br



255.
Cl
4-Cl-Ph
cPr
I



256.
Cl
4-Cl-Ph
cPr
CF3



257.
Cl
4-Cl-Ph
cPr
CH3S(O)



258.
Cl
4-Cl-Ph
cPr
CH3S(O)2



259.
Cl
4-Cl-Ph
cPr
H



260.
Cl
4-Cl-Ph
CHF2CH2
Cl



261.
Cl
4-Cl-Ph
CHF2CH2
Br



262.
Cl
4-Cl-Ph
CHF2CH2
I



263.
Cl
4-Cl-Ph
CHF2CH2
CF3



264.
Cl
4-Cl-Ph
CHF2CH2
CH3S(O)



265.
Cl
4-Cl-Ph
CHF2CH2
CH3S(O)2



266.
Cl
4-Cl-Ph
CHF2CH2
H



267.
Cl
4-Cl-Ph
CF3CH2
Cl



268.
Cl
4-Cl-Ph
CF3CH2
Br



269.
Cl
4-Cl-Ph
CF3CH2
I



270.
Cl
4-Cl-Ph
CF3CH2
CF3



271.
Cl
4-Cl-Ph
CF3CH2
CH3S(O)



272.
Cl
4-Cl-Ph
CF3CH2
CH3S(O)2



273.
Cl
4-Cl-Ph
CF3CH2
H



274.
Cl
4-CH3O-Ph
CH3
Cl



275.
Cl
4-CH3O-Ph
CH3
Br



276.
Cl
4-CH3O-Ph
CH3
I



277.
Cl
4-CH3O-Ph
CH3
CF3



278.
Cl
4-CH3O-Ph
CH3
CH3S(O)



279.
Cl
4-CH3O-Ph
CH3
CH3S(O)2



280.
Cl
4-CH3O-Ph
CH3
H



281.
Cl
4-CH3O-Ph
CH3CH2
Cl



282.
Cl
4-CH3O-Ph
CH3CH2
Br



283.
Cl
4-CH3O-Ph
CH3CH2
I



284.
Cl
4-CH3O-Ph
CH3CH2
CF3



285.
Cl
4-CH3O-Ph
CH3CH2
CH3S(O)



286.
Cl
4-CH3O-Ph
CH3CH2
CH3S(O)2



287.
Cl
4-CH3O-Ph
CH3CH2
H



288.
Cl
4-CH3O-Ph
iPr
Cl



289.
Cl
4-CH3O-Ph
iPr
Br



290.
Cl
4-CH3O-Ph
iPr
I



291.
Cl
4-CH3O-Ph
iPr
CF3



292.
Cl
4-CH3O-Ph
iPr
CH3S(O)



293.
Cl
4-CH3O-Ph
iPr
CH3S(O)2



294.
Cl
4-CH3O-Ph
iPr
H



295.
Cl
4-CH3O-Ph
cPr
Cl



296.
Cl
4-CH3O-Ph
cPr
Br



297.
Cl
4-CH3O-Ph
cPr
I



298.
Cl
4-CH3O-Ph
cPr
CF3



299.
Cl
4-CH3O-Ph
cPr
CH3S(O)



300.
Cl
4-CH3O-Ph
cPr
CH3S(O)2



301.
Cl
4-CH3O-Ph
cPr
H



302.
Cl
4-CH3O-Ph
CHF2CH2
Cl



303.
Cl
4-CH3O-Ph
CHF2CH2
Br



304.
Cl
4-CH3O-Ph
CHF2CH2
I



305.
Cl
4-CH3O-Ph
CHF2CH2
CF3



306.
Cl
4-CH3O-Ph
CHF2CH2
CH3S(O)



307.
Cl
4-CH3O-Ph
CHF2CH2
CH3S(O)2



308.
Cl
4-CH3O-Ph
CHF2CH2
H



309.
Cl
4-CH3O-Ph
CF3CH2
Cl



310.
Cl
4-CH3O-Ph
CF3CH2
Br



311.
Cl
4-CH3O-Ph
CF3CH2
I



312.
Cl
4-CH3O-Ph
CF3CH2
CF3



313.
Cl
4-CH3O-Ph
CF3CH2
CH3S(O)



314.
Cl
4-CH3O-Ph
CF3CH2
CH3S(O)2



315.
Cl
4-CH3O-Ph
CF3CH2
H















316.
Cl


embedded image


Cl






317.
Cl


embedded image


Br






318.
Cl


embedded image


I






319.
Cl


embedded image


CF3






320.
Cl


embedded image


CH3S(O)






321.
Cl


embedded image


CH3S(O)2






322.
Cl


embedded image


H






323.
Cl


embedded image


Cl






324.
Cl


embedded image


Br






325.
Cl


embedded image


I






326.
Cl


embedded image


CF3






327.
Cl


embedded image


CH3S(O)






328.
Cl


embedded image


CH3S(O)2






329.
Cl


embedded image


H






330.
Cl


embedded image


Cl






331.
Cl


embedded image


Br






332.
Cl


embedded image


I






333.
Cl


embedded image


CF3






334.
Cl


embedded image


CH3S(O)






335.
Cl


embedded image


CH3S(O)2






336.
Cl


embedded image


H






337.
Cl


embedded image


Cl






338.
Cl


embedded image


Br






339.
Cl


embedded image


I






340.
Cl


embedded image


CF3






341.
Cl


embedded image


CH3S(O)






342.
Cl


embedded image


CH3S(O)2






343.
Cl


embedded image


H
















344.
CH3
CH3
CH3
Cl



345.
CH3
CH3
CH3
Br



346.
CH3
CH3
CH3
I



347.
CH3
CH3
CH3
CF3



348.
CH3
CH3
CH3
CH3S(O)



349.
CH3
CH3
CH3
CH3S(O)2



350.
CH3
CH3
CH3
H



351.
CH3
CH3
CH3CH2
Cl



352.
CH3
CH3
CH3CH2
Br



353.
CH3
CH3
CH3CH2
I



354.
CH3
CH3
CH3CH2
CF3



355.
CH3
CH3
CH3CH2
CH3S(O)



356.
CH3
CH3
CH3CH2
CH3S(O)2



357.
CH3
CH3
CH3CH2
H



358.
CH3
CH3
iPr
Cl



359.
CH3
CH3
iPr
Br



360.
CH3
CH3
iPr
I



361.
CH3
CH3
iPr
CF3



362.
CH3
CH3
iPr
CH3S(O)



363.
CH3
CH3
iPr
CH3S(O)2



364.
CH3
CH3
iPr
H



365.
CH3
CH3
cPr
Cl



366.
CH3
CH3
cPr
Br



367.
CH3
CH3
cPr
I



368.
CH3
CH3
cPr
CF3



369.
CH3
CH3
cPr
CH3S(O)



370.
CH3
CH3
cPr
CH3S(O)2



371.
CH3
CH3
cPr
H



372.
CH3
CH3
CHF2CH2
Cl



373.
CH3
CH3
CHF2CH2
Br



374.
CH3
CH3
CHF2CH2
I



375.
CH3
CH3
CHF2CH2
CF3



376.
CH3
CH3
CHF2CH2
CH3S(O)



377.
CH3
CH3
CHF2CH2
CH3S(O)2



378.
CH3
CH3
CHF2CH2
H



379.
CH3
CH3
CF3CH2
Cl



380.
CH3
CH3
CF3CH2
Br



381.
CH3
CH3
CF3CH2
I



382.
CH3
CH3
CF3CH2
CF3



383.
CH3
CH3
CF3CH2
CH3S(O)



384.
CH3
CH3
CF3CH2
CH3S(O)2



385.
CH3
CH3
CF3CH2
H



386.
CH3
CH3CH2
CH3CH2
Cl



387.
CH3
CH3CH2
CH3CH2
Br



388.
CH3
CH3CH2
CH3CH2
I



389.
CH3
CH3CH2
CH3CH2
CF3



390.
CH3
CH3CH2
CH3CH2
CH3S(O)



391.
CH3
CH3CH2
CH3CH2
CH3S(O)2



392.
CH3
CH3CH2
CH3CH2
H



393.
CH3
CH3CH2
iPr
Cl



394.
CH3
CH3CH2
iPr
Br



395.
CH3
CH3CH2
iPr
I



396.
CH3
CH3CH2
iPr
CF3



397.
CH3
CH3CH2
iPr
CH3S(O)



398.
CH3
CH3CH2
iPr
CH3S(O)2



399.
CH3
CH3CH2
iPr
H



400.
CH3
CH3CH2
cPr
Cl



401.
CH3
CH3CH2
cPr
Br



402.
CH3
CH3CH2
cPr
I



403.
CH3
CH3CH2
cPr
CF3



404.
CH3
CH3CH2
cPr
CH3S(O)



405.
CH3
CH3CH2
cPr
CH3S(O)2



406.
CH3
CH3CH2
cPr
H



407.
CH3
CH3CH2
CHF2CH2
Cl



408.
CH3
CH3CH2
CHF2CH2
Br



409.
CH3
CH3CH2
CHF2CH2
I



410.
CH3
CH3CH2
CHF2CH2
CF3



411.
CH3
CH3CH2
CHF2CH2
CH3S(O)



412.
CH3
CH3CH2
CHF2CH2
CH3S(O)2



413.
CH3
CH3CH2
CHF2CH2
H



414.
CH3
CH3CH2
CF3CH2
Cl



415.
CH3
CH3CH2
CF3CH2
Br



416.
CH3
CH3CH2
CF3CH2
I



417.
CH3
CH3CH2
CF3CH2
CF3



418.
CH3
CH3CH2
CF3CH2
CH3S(O)



419.
CH3
CH3CH2
CF3CH2
CH3S(O)2



420.
CH3
CH3CH2
CF3CH2
H



421.
CH3
iPr
iPr
Cl



422.
CH3
iPr
iPr
Br



423.
CH3
iPr
iPr
I



424.
CH3
iPr
iPr
CF3



425.
CH3
iPr
iPr
CH3S(O)



426.
CH3
iPr
iPr
CH3S(O)2



427.
CH3
iPr
iPr
H



428.
CH3
iPr
cPr
Cl



429.
CH3
iPr
cPr
Br



430.
CH3
iPr
cPr
I



431.
CH3
iPr
cPr
CF3



432.
CH3
iPr
cPr
CH3S(O)



433.
CH3
iPr
cPr
CH3S(O)2



434.
CH3
iPr
cPr
H



435.
CH3
iPr
CHF2CH2
Cl



436.
CH3
iPr
CHF2CH2
Br



437.
CH3
iPr
CHF2CH2
I



438.
CH3
iPr
CHF2CH2
CF3



439.
CH3
iPr
CHF2CH2
CH3S(O)



440.
CH3
iPr
CHF2CH2
CH3S(O)2



441.
CH3
iPr
CHF2CH2
H



442.
CH3
iPr
CF3CH2
Cl



443.
CH3
iPr
CF3CH2
Br



444.
CH3
iPr
CF3CH2
I



445.
CH3
iPr
CF3CH2
CF3



446.
CH3
iPr
CF3CH2
CH3S(O)



447.
CH3
iPr
CF3CH2
CH3S(O)2



448.
CH3
iPr
CF3CH2
H



449.
CH3
cPr
cPr
Cl



450.
CH3
cPr
cPr
Br



451.
CH3
cPr
cPr
I



452.
CH3
cPr
cPr
CF3



453.
CH3
cPr
cPr
CH3S(O)



454.
CH3
cPr
cPr
CH3S(O)2



455.
CH3
cPr
cPr
H



456.
CH3
cPr
CHF2CH2
Cl



457.
CH3
cPr
CHF2CH2
Br



458.
CH3
cPr
CHF2CH2
I



459.
CH3
cPr
CHF2CH2
CF3



460.
CH3
cPr
CHF2CH2
CH3S(O)



461.
CH3
cPr
CHF2CH2
CH3S(O)2



462.
CH3
cPr
CHF2CH2
H



463.
CH3
cPr
CF3CH2
Cl



464.
CH3
cPr
CF3CH2
Br



465.
CH3
cPr
CF3CH2
I



466.
CH3
cPr
CF3CH2
CF3



467.
CH3
cPr
CF3CH2
CH3S(O)



468.
CH3
cPr
CF3CH2
CH3S(O)2



469.
CH3
cPr
CF3CH2
H



470.
CH3
CHF2CH2
CHF2CH2
Cl



471.
CH3
CHF2CH2
CHF2CH2
Br



472.
CH3
CHF2CH2
CHF2CH2
I



473.
CH3
CHF2CH2
CHF2CH2
CF3



474.
CH3
CHF2CH2
CHF2CH2
CH3S(O)



475.
CH3
CHF2CH2
CHF2CH2
CH3S(O)2



476.
CH3
CHF2CH2
CHF2CH2
H



477.
CH3
CHF2CH2
CF3CH2
Cl



478.
CH3
CHF2CH2
CF3CH2
Br



479.
CH3
CHF2CH2
CF3CH2
I



480.
CH3
CHF2CH2
CF3CH2
CF3



481.
CH3
CHF2CH2
CF3CH2
CH3S(O)



482.
CH3
CHF2CH2
CF3CH2
CH3S(O)2



483.
CH3
CHF2CH2
CF3CH2
H



484.
CH3
CF3CH2
CF3CH2
Cl



485.
CH3
CF3CH2
CF3CH2
Br



486.
CH3
CF3CH2
CF3CH2
I



487.
CH3
CF3CH2
CF3CH2
CF3



488.
CH3
CF3CH2
CF3CH2
CH3S(O)



489.
CH3
CF3CH2
CF3CH2
CH3S(O)2



490.
CH3
CF3CH2
CF3CH2
H



491.
CH3
CH3O
CH3
Cl



492.
CH3
CH3O
CH3
Br



493.
CH3
CH3O
CH3
I



494.
CH3
CH3O
CH3
CF3



495.
CH3
CH3O
CH3
CH3S(O)



496.
CH3
CH3O
CH3
CH3S(O)2



497.
CH3
CH3O
CH3
H



498.
CH3
CH3O
CH3CH2
Cl



499.
CH3
CH3O
CH3CH2
Br



500.
CH3
CH3O
CH3CH2
I



501.
CH3
CH3O
CH3CH2
CF3



502.
CH3
CH3O
CH3CH2
CH3S(O)



503.
CH3
CH3O
CH3CH2
CH3S(O)2



504.
CH3
CH3O
CH3CH2
H



505.
CH3
CH3O
iPr
Cl



506.
CH3
CH3O
iPr
Br



507.
CH3
CH3O
iPr
I



508.
CH3
CH3O
iPr
CF3



509.
CH3
CH3O
iPr
CH3S(O)



510.
CH3
CH3O
iPr
CH3S(O)2



511.
CH3
CH3O
iPr
H



512.
CH3
CH3O
cPr
Cl



513.
CH3
CH3O
cPr
Br



514.
CH3
CH3O
cPr
I



515.
CH3
CH3O
cPr
CF3



516.
CH3
CH3O
cPr
CH3S(O)



517.
CH3
CH3O
cPr
CH3S(O)2



518.
CH3
CH3O
cPr
H



519.
CH3
CH3O
CHF2CH2
Cl



520.
CH3
CH3O
CHF2CH2
Br



521.
CH3
CH3O
CHF2CH2
I



522.
CH3
CH3O
CHF2CH2
CF3



523.
CH3
CH3O
CHF2CH2
CH3S(O)



524.
CH3
CH3O
CHF2CH2
CH3S(O)2



525.
CH3
CH3O
CHF2CH2
H



526.
CH3
CH3O
CF3CH2
Cl



527.
CH3
CH3O
CF3CH2
Br



528.
CH3
CH3O
CF3CH2
I



529.
CH3
CH3O
CF3CH2
CF3



530.
CH3
CH3O
CF3CH2
CH3S(O)



531.
CH3
CH3O
CF3CH2
CH3S(O)2



532.
CH3
CH3O
CF3CH2
H



533.
CH3
Ph
CH3
Cl



534.
CH3
Ph
CH3
Br



535.
CH3
Ph
CH3
I



536.
CH3
Ph
CH3
CF3



537.
CH3
Ph
CH3
CH3S(O)



538.
CH3
Ph
CH3
CH3S(O)2



539.
CH3
Ph
CH3
H



540.
CH3
Ph
CH3CH2
Cl



541.
CH3
Ph
CH3CH2
Br



542.
CH3
Ph
CH3CH2
I



543.
CH3
Ph
CH3CH2
CF3



544.
CH3
Ph
CH3CH2
CH3S(O)



545.
CH3
Ph
CH3CH2
CH3S(O)2



546.
CH3
Ph
CH3CH2
H



547.
CH3
Ph
iPr
Cl



548.
CH3
Ph
iPr
Br



549.
CH3
Ph
iPr
I



550.
CH3
Ph
iPr
CF3



551.
CH3
Ph
iPr
CH3S(O)



552.
CH3
Ph
iPr
CH3S(O)2



553.
CH3
Ph
iPr
H



554.
CH3
Ph
cPr
Cl



555.
CH3
Ph
cPr
Br



556.
CH3
Ph
cPr
I



557.
CH3
Ph
cPr
CF3



558.
CH3
Ph
cPr
CH3S(O)



559.
CH3
Ph
cPr
CH3S(O)2



560.
CH3
Ph
cPr
H



561.
CH3
Ph
CHF2CH2
Cl



562.
CH3
Ph
CHF2CH2
Br



563.
CH3
Ph
CHF2CH2
I



564.
CH3
Ph
CHF2CH2
CF3



565.
CH3
Ph
CHF2CH2
CH3S(O)



566.
CH3
Ph
CHF2CH2
CH3S(O)2



567.
CH3
Ph
CHF2CH2
H



568.
CH3
Ph
CF3CH2
Cl



569.
CH3
Ph
CF3CH2
Br



570.
CH3
Ph
CF3CH2
I



571.
CH3
Ph
CF3CH2
CF3



572.
CH3
Ph
CF3CH2
CH3S(O)



573.
CH3
Ph
CF3CH2
CH3S(O)2



574.
CH3
Ph
CF3CH2
H



575.
CH3
4-Cl-Ph
CH3
Cl



576.
CH3
4-Cl-Ph
CH3
Br



577.
CH3
4-Cl-Ph
CH3
I



578.
CH3
4-Cl-Ph
CH3
CF3



579.
CH3
4-Cl-Ph
CH3
CH3S(O)



580.
CH3
4-Cl-Ph
CH3
CH3S(O)2



581.
CH3
4-Cl-Ph
CH3
Z



582.
CH3
4-Cl-Ph
CH3CH2
Cl



583.
CH3
4-Cl-Ph
CH3CH2
Br



584.
CH3
4-Cl-Ph
CH3CH2
I



585.
CH3
4-Cl-Ph
CH3CH2
CF3



586.
CH3
4-Cl-Ph
CH3CH2
CH3S(O)



587.
CH3
4-Cl-Ph
CH3CH2
CH3S(O)2



588.
CH3
4-Cl-Ph
CH3CH2
H



589.
CH3
4-Cl-Ph
iPr
Cl



590.
CH3
4-Cl-Ph
iPr
Br



591.
CH3
4-Cl-Ph
iPr
I



592.
CH3
4-Cl-Ph
iPr
CF3



593.
CH3
4-Cl-Ph
iPr
CH3S(O)



594.
CH3
4-Cl-Ph
iPr
CH3S(O)2



595.
CH3
4-Cl-Ph
iPr
H



596.
CH3
4-Cl-Ph
cPr
Cl



597.
CH3
4-Cl-Ph
cPr
Br



598.
CH3
4-Cl-Ph
cPr
I



599.
CH3
4-Cl-Ph
cPr
CF3



600.
CH3
4-Cl-Ph
cPr
CH3S(O)



601.
CH3
4-Cl-Ph
cPr
CH3S(O)2



602.
CH3
4-Cl-Ph
cPr
H



603.
CH3
4-Cl-Ph
CHF2CH2
Cl



604.
CH3
4-Cl-Ph
CHF2CH2
Br



605.
CH3
4-Cl-Ph
CHF2CH2
I



606.
CH3
4-Cl-Ph
CHF2CH2
CF3



607.
CH3
4-Cl-Ph
CHF2CH2
CH3S(O)



608.
CH3
4-Cl-Ph
CHF2CH2
CH3S(O)2



609.
CH3
4-Cl-Ph
CHF2CH2
H



610.
CH3
4-Cl-Ph
CF3CH2
Cl



611.
CH3
4-Cl-Ph
CF3CH2
Br



612.
CH3
4-Cl-Ph
CF3CH2
I



613.
CH3
4-Cl-Ph
CF3CH2
CF3



614.
CH3
4-Cl-Ph
CF3CH2
CH3S(O)



615.
CH3
4-Cl-Ph
CF3CH2
CH3S(O)2



616.
CH3
4-Cl-Ph
CF3CH2
H



617.
CH3
4-CH3O-Ph
CH3
Cl



618.
CH3
4-CH3O-Ph
CH3
Br



619.
CH3
4-CH3O-Ph
CH3
I



620.
CH3
4-CH3O-Ph
CH3
CF3



621.
CH3
4-CH3O-Ph
CH3
CH3S(O)



622.
CH3
4-CH3O-Ph
CH3
CH3S(O)2



623.
CH3
4-CH3O-Ph
CH3
H



624.
CH3
4-CH3O-Ph
CH3CH2
Cl



625.
CH3
4-CH3O-Ph
CH3CH2
Br



626.
CH3
4-CH3O-Ph
CH3CH2
I



627.
CH3
4-CH3O-Ph
CH3CH2
CF3



628.
CH3
4-CH3O-Ph
CH3CH2
CH3S(O)



629.
CH3
4-CH3O-Ph
CH3CH2
CH3S(O)2



630.
CH3
4-CH3O-Ph
CH3CH2
H



631.
CH3
4-CH3O-Ph
iPr
Cl



632.
CH3
4-CH3O-Ph
iPr
Br



633.
CH3
4-CH3O-Ph
iPr
I



634.
CH3
4-CH3O-Ph
iPr
CF3



635.
CH3
4-CH3O-Ph
iPr
CH3S(O)



636.
CH3
4-CH3O-Ph
iPr
CH3S(O)2



637.
CH3
4-CH3O-Ph
iPr
H



638.
CH3
4-CH3O-Ph
cPr
Cl



639.
CH3
4-CH3O-Ph
cPr
Br



640.
CH3
4-CH3O-Ph
cPr
I



641.
CH3
4-CH3O-Ph
cPr
CF3



642.
CH3
4-CH3O-Ph
cPr
CH3S(O)



643.
CH3
4-CH3O-Ph
cPr
CH3S(O)2



644.
CH3
4-CH3O-Ph
cPr
H



645.
CH3
4-CH3O-Ph
CHF2CH2
Cl



646.
CH3
4-CH3O-Ph
CHF2CH2
Br



647.
CH3
4-CH3O-Ph
CHF2CH2
I



648.
CH3
4-CH3O-Ph
CHF2CH2
CF3



649.
CH3
4-CH3O-Ph
CHF2CH2
CH3S(O)



650.
CH3
4-CH3O-Ph
CHF2CH2
CH3S(O)2



651.
CH3
4-CH3O-Ph
CHF2CH2
H



652.
CH3
4-CH3O-Ph
CF3CH2
Cl



653.
CH3
4-CH3O-Ph
CF3CH2
Br



654.
CH3
4-CH3O-Ph
CF3CH2
I



655.
CH3
4-CH3O-Ph
CF3CH2
CF3



656.
CH3
4-CH3O-Ph
CF3CH2
CH3S(O)



657.
CH3
4-CH3O-Ph
CF3CH2
CH3S(O)2



658.
CH3
4-CH3O-Ph
CF3CH2
H















659.
CH3


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Cl






660.
CH3


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Br






661.
CH3


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I






662.
CH3


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CF3






663.
CH3


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CH3S(O)






664.
CH3


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CH3S(O)2






665.
CH3


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H






666.
CH3


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Cl






667.
CH3


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Br






668.
CH3


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I






669.
CH3


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CF3






670.
CH3


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CH3S(O)






671.
CH3


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CH3S(O)2






672.
CH3


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H






673.
CH3


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Cl






674.
CH3


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Br






675.
CH3


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I






676.
CH3


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CF3






677.
CH3


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CH3S(O)






678.
CH3


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CH3S(O)2






679.
CH3


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H






680.
CH3


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Cl






681.
CH3


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Br






682.
CH3


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I






683.
CH3


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CF3






684.
CH3


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CH3S(O)






685.
CH3


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CH3S(O)2






686.
CH3


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H









In Table A, cPr means cyclopropyl and iPr means isopropyl (=1-methylethyl).


It is apparent to a skilled person that in lines 316 to 343 and in lines 659 to 686 of table A the meanings given for the combination R2/R2d relate to the moiety NR2cR2d in formulae I.A.1 to I.D.VI.


Amongst the combinations of variables R1, R2c, R2d and R3, those are preferred, where R1 is CH3 and where R3 is H, Cl, Br or CF3.


Amongst the combinations of variables R1, R2c, R2d and R3, those are preferred, where R1 is Cl and where R3 is H, Cl, Br or CF3.


Amongst the combinations of variables R1, R2c, R2d and R3, those are preferred, where R1 is Cl or CH3, R2c is CH3 or C2H5, R2d is CH2CF3 and where R3 is H, Cl, Br or CF3.


Particular preference is given to compounds of the formula formulae I.A.I and I.A.VII, where R1, R2c, R2d and R3 are as defined in Table A and where R1, R2c, R2d and R3 are in particular as defined in the following tables A′ and A″.


Particular preference is also given to compounds of the formulae I.D.I and I.D.VII, where R1, R2c, R2d and R3 are as defined in Table A and where R1, R2c, R2d and R3 are in particular as defined in the following tables A′ and A″.














TABLE A′







R1
R2c
R2d
R3






















687.
CH3
CH3
CH3
H



688.
CH3
CH3
CH2CH3
H



689.
CH3
CH3
CH2CH3
H



690.
CH3
CH2CH3
CH2CH3
H



691.
CH3
CH3
CH2CH3
H



692.
CH3
CH2CH3
CH2CH3
H



693.
CH3
CH3
CH2CHF2
H



694.
CH3
CH2CH3
CH2CHF2
H



695.
CH3
CH3
CH(CH3)2
H



696.
CH3
c-C3H5
c-C3H5
H



697.
Cl
CH3
CH3
H



698.
Cl
CH3
CH2CH3
H



699.
Cl
CH2CH3
CH2CH3
H



700.
Cl
CH3
CH2CH3
H



701.
Cl
CH2CH3
CH2CH3
H



702.
Cl
CH3
CH2CHF2
H



703.
Cl
CH2CH3
CH2CHF2
H



704.
Cl
CH3
CH(CH3)2
H



705.
Cl
c-C3H5
c-C3H5
H



706.
CH3
CH3
CH3
Cl



707.
CH3
CH3
CH2CH3
Cl



708.
CH3
CH3
CH2CH3
Cl



709.
CH3
CH2CH3
CH2CH3
Cl



710.
CH3
CH3
CH2CF3
Cl



711.
CH3
CH2CH3
CH2CF3
Cl



712.
CH3
CH3
CH2CHF2
Cl



713.
CH3
CH2CH3
CH2CHF2
Cl



714.
CH3
CH3
CH(CH3)2
Cl



715.
CH3
c-C3H5
c-C3H5
Cl



716.
Cl
CH3
CH3
Cl



717.
Cl
CH3
CH2CH3
Cl



718.
Cl
CH2CH3
CH2CH3
Cl



719.
Cl
CH3
CH2CF3
Cl



720.
Cl
CH2CH3
CH2CF3
Cl



721.
Cl
CH3
CH2CHF2
Cl



722.
Cl
CH2CH3
CH2CHF2
Cl



723.
Cl
CH3
CH(CH3)2
Cl



724.
Cl
c-C3H5
c-C3H5
Cl



725.
CH3
CH3
CH3
Br



726.
CH3
CH3
CH2CH3
Br



727.
CH3
CH2CH3
CH2CH3
Br



728.
CH3
CH3
CH2CF3
Br



729.
CH3
CH2CH3
CH2CF3
Br



730.
CH3
CH3
CH2CHF2
Br



731.
CH3
CH2CH3
CH2CHF2
Br



732.
CH3
CH3
CH(CH3)2
Br



733.
CH3
c-C3H5
c-C3H5
Br



734.
Cl
CH3
CH3
Br



735.
Cl
CH3
CH2CH3
Br



736.
Cl
CH2CH3
CH2CH3
Br



737.
Cl
CH3
CH2CF3
Br



738.
Cl
CH2CH3
CH2CF3
Br



739.
Cl
CH3
CH2CHF2
Br



740.
Cl
CH2CH3
CH2CHF2
Br



741.
Cl
CH3
CH(CH3)2
Br



742.
Cl
c-C3H5
c-C3H5
Br



743.
CH3
CH3
CH3
CF3



744.
CH3
CH3
CH2CH3
CF3



745.
CH3
CH2CH3
CH2CH3
CF3



746.
CH3
CH3
CH2CF3
CF3



747.
CH3
CH2CH3
CH2CF3
CF3



748.
CH3
CH3
CH2CHF2
CF3



749.
CH3
CH2CH3
CH2CHF2
CF3



750.
CH3
CH3
CH(CH3)2
CF3



751.
CH3
c-C3H5
c-C3H5
CF3



752.
Cl
CH3
CH3
CF3



753.
Cl
CH3
CH2CH3
CF3



754.
Cl
CH2CH3
CH2CH3
CF3



755.
Cl
CH3
CH2CF3
CF3



756.
Cl
CH2CH3
CH2CF3
CF3



757.
Cl
CH3
CH2CHF2
CF3



758.
Cl
CH2CH3
CH2CHF2
CF3



759.
Cl
CH3
CH(CH3)2
CF3



760.
Cl
c-C3H5
c-C3H5
CF3





















TABLE A″







R1
NR2cR2d
R3





















761.
CH3
pyrrolidin-1-yl
H



762.
CH3
piperidin-1-yl
H



763.
CH3
morpholin-4-yl
H



764.
CH3
2,6-dimethylmorpholin-4-yl
H



765.
Cl
pyrrolidin-1-yl
H



766.
Cl
piperidin-1-yl
H



767.
Cl
morpholin-4-yl
H



768.
Cl
2,6-dimethylmorpholin-4-yl
H



769.
CH3
pyrrolidin-1-yl
Cl



770.
CH3
piperidin-1-yl
Cl



771.
CH3
morpholin-4-yl
Cl



772.
CH3
2,6-dimethylmorpholin-4-yl
Cl



773.
Cl
pyrrolidin-1-yl
Cl



774.
Cl
piperidin-1-yl
Cl



775.
Cl
morpholin-4-yl
Cl



776.
Cl
2,6-dimethylmorpholin-4-yl
Cl



777.
CH3
pyrrolidin-1-yl
Br



778.
CH3
piperidin-1-yl
Br



779.
CH3
morpholin-4-yl
Br



780.
CH3
2,6-dimethylmorpholin-4-yl
Br



781.
Cl
pyrrolidin-1-yl
Br



782.
Cl
piperidin-1-yl
Br



783.
Cl
morpholin-4-yl
Br



784.
Cl
2,6-dimethylmorpholin-4-yl
Br



785.
CH3
pyrrolidin-1-yl
CF3



786.
CH3
piperidin-1-yl
CF3



787.
CH3
morpholin-4-yl
CF3



788.
CH3
2,6-dimethylmorpholin-4-yl
CF3



789.
Cl
pyrrolidin-1-yl
CF3



790.
Cl
piperidin-1-yl
CF3



791.
Cl
morpholin-4-yl
CF3



792.
Cl
2,6-dimethylmorpholin-4-yl
CF3










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.




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Likewise, the compounds of formula I.B can be prepared analogous to Scheme 2 below:




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Likewise, the compounds of formula I.C can be prepared analogous to Scheme 3 below:




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Likewise, the compounds of formula I.D can be prepared analogous to Scheme 4 below:




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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 compounds of the formula I.D. Herein, X is a leaving group, such as halogen, in particular Cl, an anhydride residue or an active ester residue, such as pentafluorophenoxy. 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 triethylamine, 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, chlorobenzene, 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, N,N-dimethyl formamide, N-methyl pyrrolidinone 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. Likewise, reaction of a 4-amino-1,2,5-oxadiazole compound V with a benzoic acid derivative of formula VI yields compound I.C. Likewise, 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. N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone. The reaction is ordinarily carried out at temperatures in the range from −20° C. to +25° C.




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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).




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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).




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As shown in Scheme 11, 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 in Zeitschrift für Chemie, 1990, 30, 12, 436-437.




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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.




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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, U.S. Pat. No. 6,277,847.


The 4-amino-1,2,5-oxadiazole compounds of the formula V are either commercially available 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.




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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).




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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. halogen, in the 4-position of the 1,2,5-oxadiazoles compounds of formula IX in accordance to procedures 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).




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The compounds of the formula (VI), where R2 is Z2—NH—C(O)—NR2cR2d can be prepared from the corresponding substituted 3-aminobenzoates of the formula (X), which comprises reacting the compound of formula (X) with phosgene or a phosgene equivalent (XI), such as diphosgene, i.e. trichloromethyl chloroformate, or triphosgene, i.e. bis-trichloromethylcarbonate, and a secondary amine of the formula (XII), followed by subsequent hydrolysis as depicted in the following scheme 1. Instead of phosgene or the phosgene equivalent carbonyldiimidazole may be used.




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In scheme 16, alkyl means lower alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl. The reaction of the compound of the formula (X) with phosgene or phosgene equivalent (XI) and the secondary amine of formula (XII) can be performed by analogy to the preparation of mixed ureas by reaction of two different amine with phosgene or phosgene equivalent. Preferably, the compound of the formula (X) is firstly reacted with phosgene or phosgene equivalent (XI) to obtain an intermediate compound or compound mixture, which is subsequently reacted with the secondary amine of the formula I (XII). The intermediate compound or compound mixture may be isolated from the reaction mixture. For economical reasons, the intermediate compound or compound mixture is usually not isolated but the reaction mixture obtained from the reaction of the compound (X) with the phosgene or phosgene equivalent (XI) is subjected to the reaction with the secondary amine of formula (XII). Compounds of formula (II) can be easily prepared from the compounds of formula (VI) by standard procedures.


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 recrystallization 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 carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.


The compounds of the present invention are particularly suitable for use in crops from the family poaceae, in particular crops of the tribum triticeae, e.g. crops of the generae Hordeum, Sorghum, Triticium and Secale, and crops of the generae Zea, e.g. Zea mays and Oryza, e.g. Oryza sativa.


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 hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659) or imidazolinones (see, for example, U.S. Pat. No. 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, glyphosate (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, U.S. Pat. No. 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 “herbicidetolerant” 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 hydroxyphenyl pyruvate dioxygenase (mutated HPPD)” refers to the replacement of an amino acid of the wild-type primary sequences SEQ ID NO: 2, 5, 8, 11, 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 et al., Eur. J. Biochem., 205, 459-466, 1992, WO96/38567), of plants such as Arabidopsis (WO96/38567, Genebank AF047834) or of carrot (WO96/38567, Genebank 87257), of Coccicoides (Genebank COITRP), HPPDs of Brassica, cotton, Synechocystis, and tomato (U.S. Pat. No. 7,297,541), of mammals such as the mouse or the pig. Furthermore, artificial HPPD sequences have been described, for example in U.S. Pat. Nos. 6,768,044; 6,268,549;


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 techniques. 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, 11, 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 example, 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, 11, 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 equivalent (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 unbranched 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 residues. 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 (calmodulin-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 α-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, Ohio), QuikChange Site Directed mutagenesis (Stratagene, San Diego, Calif.), 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 altered 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 Terpe, Appl. Microbiol. Biotechnol. 60, 523-533, 2003).


“Orthologues” and “paralogues” encompass evolutionary concepts used to describe the ancestral 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. Identified 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., pp 53-61, 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 Needleman 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 T F, Waterman M S (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, 11, 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 activity 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 embodiment the mutated HPPD useful for the present invention comprises a sequence of SEQ ID NO: 2, 5, 8, 11, 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 homologue 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 B.a.









TABLE B.a







(Sequence ID No: 2): single amino acid substitutions










Key amino acid position
Substituents







Val212
Ile, Leu



Val213
Thr, Ala



Asn215
Ala, His



Ala236
Leu, Ser, Arg



Phe238
Val, Ala



Leu250
Val, Met



Ser252
Thr



Pro265
Ala



Asn267
Tyr, Gln



Gln278
His, Asn, Ser



Ile279
Thr



Arg309
Lys, Ala



Leu320
Asn, Gln, His, Tyr,



Pro321
Ala, Arg, Gly, Asn



Leu334
Glu, Cys



Leu353
Met, Tyr, Ala, Ser



Phe366
Ile, Leu, Tyr



Gly371
Ile, Phe



Thr375
Pro



Phe377
Ala, Leu, Ser



Gly403
Arg



Phe404
Leu, Pro



Lys406
Thr



Gly407
Cys, His



Phe409
Ile, His



Glu411
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 B.b.









TABLE B.b







(with reference to Sequence ID No: 2):


combined amino acid substitutions








Combination No
Key amino acid position and and its substitutents











1
A236L, E411T


2
L320H, P321A


3
L320H, P321R


4
L320N, P321A


5
L320N, P321R


6
L320Q, P321A


7
L320Q, P321R


8
L320Y, P321A


9
L320Y, P321R


10
L353M, P321R


11
L353M, P321R, A236L


12
L353M, P321R, A236L, E411T


13
L353M, P321R, E411T


14
L353M, P321R, L320H


15
L353M, P321R, L320N


16
L353M, P321R, L320Q


17
L353M, P321R, L320Y


18
L353M, P321R, V212I


19
L353M, P321R, V212I, L334E


20
L353M, P321R, V212L, L334E


21
L353M, P321R, V212L, L334E, A236L


22
L353M, P321R, V212L, L334E, A236L, E411T


23
L353M, P321R, V212L, L334E, E411T


24
L353M, P321R, V212L, L334E, L320H


25
L353M, P321R, V212L, L334E, L320N


26
L353M, P321R, V212L, L334E, L320Q


27
L353M, P321R, 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 B.c.









TABLE B.c







(Sequence ID No: 53): single amino acid substitutions









Key amino acid position
Substituents
Preferred substituents





Val228
Thr, Ala
Thr, Ala


Asn230
Ala, His
Ala, His


Ala251
Ser, Arg
Ser, Arg


Phe253
Val, Ala
Val, Ala


Leu265
Val, Met
Val, Met


Ser267
Thr
Thr


Pro280
Ala
Ala


Asn282
Tyr, Gln
Tyr, Gln


Lys291
Arg, Ala
Arg


Gln293
Ala, Leu, Ile, Val, His, Asn, Ser
His, Asn, Ser


Ile294
Thr
Thr


Arg324
Lys, Ala
Lys, Ala


Met335
Ala, Trp, Phe, Leu, Ile, Val, Asn, Gln,
Gln, 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
Gln
Gln


Leu368
Met, Tyr,
Met


Phe381
Ile, Leu, Tyr
Ile, Leu


Leu385
Ala, Val, Gln, Asp
Val, Asp


Gly386
Ile, Phe
Ile, 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
Ile, His
Ile, 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 paralogue thereof, 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 B.d.









TABLE B.d







(reference to Sequence ID No: 53): combined amino acid substitutions










Combination
Key amino acid

Preferred


No
position
Substituents
substituents





1
Pro336
Ala, Arg
Ala



Glu363
Gln
Gln


2
Pro336
Ala, Arg
Ala



Glu363
Gln
Gln



Leu385
Ala, Val
Val


3
Pro336
Ala, Arg
Ala



Glu363
Gln
Gln



Leu385
Ala, Val
Val



Ile393
Ala, Leu
Leu


4
Leu385
Ala, Val
Val



Ile393
Ala, Leu
Leu


5
Met335
Ala, Trp, Phe, Leu, Ile, Val, Asn,
Gln, Asn,




Gln, His, Tyr, Ser, Thr, Cys
His, Tyr



Pro336
Ala, Arg, Gly
Ala, Gly


6
Met335
Ala, Trp, Phe, Leu, Ile, Val, Asn,
Gln, Asn,




Gln, His, Tyr, Ser, Thr, Cys
His, Tyr



Pro336
Ala, Arg, Gly
Ala, Gly



Glu363
Gln
Gln


7
Met335
Ala, Trp, Phe, Leu, Ile, Val, Asn,
Gln, Asn, His,




Gln, 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 position 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 Gln, 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 Ile, the amino acid corresponding to or at position 374 is other than Phe, the amino acid corresponding to or at position 375 is other than Ile, 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 Ile, 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, Gln, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Gln


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 Gln, and the amino acid corresponding to or at position 341 is Ile.


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 Gln, 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 Gln, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Ile, 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, Gln, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Gln.


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, Gln, Glu, Gly, His, Ile, 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 Gln.


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 Gln.


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, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val, particularly preferred Ile.


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, Gln, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Glu, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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, Gln, Gly, His, Ile, 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, Gln, Gly, His, Ile, 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, Gln, Glu, Gly, His, Ile, 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 amino 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, Gln, Glu, Gly, His, Ile, Leu, Lys, Met, Pro, Ser, Thr, Trp, Tyr, or Val.


Following mutagenesis of one of the sequences as shown herein, the encoded protein can be expressed recombinantly and the activity of the protein can be determined using, for example, assays described herein.


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, 11, 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 B.a and B.b, B.c, and B.d can be chosen to be substituted by any other amino acid by conserved amino acids, and more preferably by the amino acids of tables B.a and B.b, B.c, and B.d.


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® (glyphosate) 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 Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-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 Streptomycetes; plant lectins, for example from peas or barley; agglutinins; proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribosome-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 pretoxins, hybrid proteins or truncated or otherwise modified proteins. Hybrid proteins are characterized 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, EPA 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 publications 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 toxins 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 Cry1Ab), YieldGard® Plus (corn varieties which produce the toxins Cry1Ab and Cry3Bb1), Starlink® (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 Cry1Ac), Bollgard® I (cotton varieties which produce the toxin Cry1Ac), Bollgard® II (cotton varieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cotton varieties which produce a VIP toxin); NewLeaf® (potato varieties which produce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin Cry1Ab and the PAT enzyme), 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 Cry1Ac) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1F 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 monounsaturated 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 112 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 112, 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 Ia, 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 cyclohexanone 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 suspension 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 safeners, also termed herbicide safener. 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-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, 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 compounds having herbicidal activity (herbicides B) or growth-regulating activity, optionally in combination with safeners. Suitable mixing partners are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryl-oxyalkanoic 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, dihydrofuran-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 heteroaryloxyphenoxypropionic 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 B 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 B 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, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2″,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5), 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, bispyribacsodium, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam, cloransulammethyl, 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, imazethapyr, 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, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron;


b3) from the group of the photosynthesis inhibitors:


ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenoxim, bromoxynil and its salts and esters, chlorobromuron, chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquatdibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquatdimetilsulfate, pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thidiazuron, trietazine, 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methylpyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazo]-3-yl]imidazolidin-2-one (CAS 2023785-80-8) and 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methylimidazolidin-2-one (CAS 1844836-64-1);


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


acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-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-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-3; CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-4; CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-5; CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-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 (trifludimoxazin), 2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione (CAS 1300118-96-0), 1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4);


b5) from the group of the bleacher herbicides:


aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone, diflufenican, fenquinotrione, flumeturon, fluridone, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, oxotrione (CAS 1486617-21-3), picolinafen, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, 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, bicyclopyrone), 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (H-8; CAS 180608-33-7), 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethypenzamide (CAS 1361139-71-0), 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);


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, chlorpropham, 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, dimethenamid-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:




embedded image


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 C1-C4-alkyl; X is O or NH; N is 0 or 1.


Compounds of the formula 2 have in particular the following meanings:

    • Y is




embedded image


where # denotes the bond to the skeleton of the molecule; and


R21, R22, R23, R24 are H, Cl, F or CH3; R25 is halogen, C1-C4-alkyl or C1-C4-haloalkyl; R26 is C1-C4-alkyl; R27 is halogen, C1-C4-alkoxy or C1-C4-haloalkoxy; R28 is H, halogen, C1-C4-alkyl, C1-C4-haloalkyl or C1-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:

    • Y is




embedded image


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-1H-pyrazol-4-ylmethanesulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-1); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-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-1H-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-1H-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);


b11) 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, halauxifen and its salts and esters, 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, 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS 858956-C8-8) and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6);


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, chlorflurenolmethyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, 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, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (H-11; 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 97/41116, WO 97/41117, WO 97/41118, 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 combinations comprising at least one benzamide compound of the formula I and at least one further active compound, in particular a compound having herbicide activity (herbicide B) preferably selected from the active compounds of groups b1 to b15, and/or a safener C.


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 comprising at least one benzamide compound of the formula I and at least one further active compound, in particular a compound having herbicide activity (herbicide B) 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 formulated as a 1-component composition comprising an active compound combination comprising at least one benzamide compound of the formula I and at least one safener C 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 formulated as a 1-component composition comprising an active compound combination comprising at least one benzamide compound of the formula I and at least one further active compound, in particular a compound having herbicide activity (herbicide B) which is preferably selected from the active compounds of groups b1 to b15, a safener C 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 formulated 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, in particular a compound having herbicide activity (herbicide B) which is preferably 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.


The invention also relates to compositions in the form of a crop protection composition formulated 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, in particular a compound having herbicide activity (herbicide B) which is preferably 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, where the first component or the second component further comprises a safener C.


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 combinations B-1 to B-1406 listed in Table B below, where in each case one row of Table B corresponds to a herbicidal composition comprising 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







Herbicide(s) B
Safener C


















B-1
clodinafop-propargyl
—


B-2
cycloxydim
—


B-3
cyhalofop-butyl
—


B-4
fenoxaprop-P-ethyl
—


B-5
pinoxaden
—


B-6
profoxydim
—


B-7
tepraloxydim
—


B-8
tralkoxydim
—


B-9
esprocarb
—


B-10
prosulfocarb
—


B-11
thiobencarb
—


B-12
triallate
—


B-13
bensulfuron-methyl
—


B-14
bispyribac-sodium
—


B-15
cyclosulfamuron
—


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
—


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
pinoxaden
—


B-95
sethoxydim
—


B-96
clethodim
—


B-97
diclofop
—


B-98
quizalofop
—


B-99
thifensulfuron
—


B-100
tribenuron
—


B-101
metsulfuron
—


B-102
foramsulfuron
—


B-103
chlorimuron
—


B-104
chlorsulfuron
—


B-105
flucarbazone-sodium
—


B-106
propoxycarbazone-sodium
—


B-107
ethalfluralin
—


B-108
halauxifen
—


B-109
MCPA
—


B-110
bromoxynil
—


B-111
bentazone
—


B-112
carfentrazone
—


B-113
trifludimoxazin
—


B-114
bicyclopyrone
—


B-115
benzobicyclon
—


B-116
pyrasulfotole
—


B-117
diquat
—


B-118
cinmethylin
—


B-119
acetochlor
—


B-120
naptalam
—


B-121
atrazine + H-1
—


B-122
atrazine + glyphosate
—


B-123
atrazine + mesotrione
—


B-124
atrazine + nicosulfuron
—


B-125
atrazine + tembotrione
—


B-126
atrazine + topramezone
—


B-127
clomazone + glyphosate
—


B-128
diflufenican + clodinafop-propargyl
—


B-129
diflufenican + fenoxaprop-P-ethyl
—


B-130
diflufenican + flupyrsulfuron-methyl-sodium
—


B-131
diflufenican + glyphosate
—


B-132
diflufenican + mesosulfuron-methyl
—


B-133
diflufenican + pinoxaden
—


B-134
diflufenican + pyroxsulam
—


B-135
flumetsulam + glyphosate
—


B-136
flumioxazin + glyphosate
—


B-137
imazapic + glyphosate
—


B-138
imazethapyr + glyphosate
—


B-139
isoxaflutol + H-1
—


B-140
isoxaflutol + glyphosate
—


B-141
metazachlor + H-1
—


B-142
metazachlor + glyphosate
—


B-143
metazachlor + mesotrione
—


B-144
metazachlor + nicosulfuron
—


B-145
metazachlor + terbuthylazine
—


B-146
metazachlor + topramezone
—


B-147
metribuzin + glyphosate
—


B-148
pendimethalin + H-1
—


B-149
pendimethalin + clodinafop-propargyl
—


B-150
pendimethalin + fenoxaprop-P-ethyl
—


B-151
pendimethalin + flupyrsulfuron-methyl-sodium
—


B-152
pendimethalin + glyphosate
—


B-153
pendimethalin + mesosulfuron-methyl
—


B-154
pendimethalin + mesotrione
—


B-155
pendimethalin + nicosulfuron
—


B-156
pendimethalin + pinoxaden
—


B-157
pendimethalin + pyroxsulam
—


B-158
pendimethalin + tembotrione
—


B-159
pendimethalin + topramezone
—


B-160
pyroxasulfone + tembotrione
—


B-161
pyroxasulfone + topramezone
—


B-162
sulfentrazone + glyphosate
—


B-163
terbuthylazine + H-1
—


B-164
terbuthylazine + foramsulfuron
—


B-165
terbuthylazine + glyphosate
—


B-166
terbuthylazine + mesotrione
—


B-167
terbuthylazine + nicosulfuron
—


B-168
terbuthylazine + tembotrione
—


B-169
terbuthylazine + topramezone
—


B-170
trifluralin + glyphosate
—


B-171
—
benoxacor


B-172
—
cloquintocet


B-173
—
cyprosulfamide


B-174
—
dichlormid


B-175
—
fenchlorazole


B-176
—
fenclorim


B-177
—
isoxadifen


B-178
—
mefenpyr


B-179
—
H-11


B-180
—
H-12


B-181
clodinafop-propargyl
benoxacor


B-182
cycloxydim
benoxacor


B-183
cyhalofop-butyl
benoxacor


B-184
fenoxaprop-P-ethyl
benoxacor


B-185
pinoxaden
benoxacor


B-186
profoxydim
benoxacor


B-187
tepraloxydim
benoxacor


B-188
tralkoxydim
benoxacor


B-189
esprocarb
benoxacor


B-190
prosulfocarb
benoxacor


B-191
thiobencarb
benoxacor


B-192
triallate
benoxacor


B-193
bensulfuron-methyl
benoxacor


B-194
bispyribac-sodium
benoxacor


B-195
cyclosulfamuron
benoxacor


B-196
flumetsulam
benoxacor


B-197
flupyrsulfuron-methyl-sodium
benoxacor


B-198
foramsulfuron
benoxacor


B-199
imazamox
benoxacor


B-200
imazapic
benoxacor


B-201
imazapyr
benoxacor


B-202
imazaquin
benoxacor


B-203
imazethapyr
benoxacor


B-204
imazosulfuron
benoxacor


B-205
iodosulfuron-methyl-sodium
benoxacor


B-206
mesosulfuron
benoxacor


B-207
nicosulfuron
benoxacor


B-208
penoxsulam
benoxacor


B-209
propoxycarbazone-sodium
benoxacor


B-210
pyrazosulfuron-ethyl
benoxacor


B-211
pyroxsulam
benoxacor


B-212
rimsulfuron
benoxacor


B-213
sulfosulfuron
benoxacor


B-214
thiencarbazone-methyl
benoxacor


B-215
tritosulfuron
benoxacor


B-216
2,4-D and its salts and esters
benoxacor


B-217
aminopyralid and its salts and esters
benoxacor


B-218
clopyralid and its salts and esters
benoxacor


B-219
dicamba and its salts and esters
benoxacor


B-220
fluroxypyr-meptyl
benoxacor


B-221
quinclorac
benoxacor


B-222
quinmerac
benoxacor


B-223
H-9
benoxacor


B-224
diflufenzopyr
benoxacor


B-225
diflufenzopyr-sodium
benoxacor


B-226
clomazone
benoxacor


B-227
diflufenican
benoxacor


B-228
fluorochloridone
benoxacor


B-229
isoxaflutol
benoxacor


B-230
mesotrione
benoxacor


B-231
picolinafen
benoxacor


B-232
sulcotrione
benoxacor


B-233
tefuryltrione
benoxacor


B-234
tembotrione
benoxacor


B-235
topramezone
benoxacor


B-236
H-7
benoxacor


B-237
atrazine
benoxacor


B-238
diuron
benoxacor


B-239
fluometuron
benoxacor


B-240
hexazinone
benoxacor


B-241
isoproturon
benoxacor


B-242
metribuzin
benoxacor


B-243
propanil
benoxacor


B-244
terbuthylazine
benoxacor


B-245
paraquat dichloride
benoxacor


B-246
flumioxazin
benoxacor


B-247
oxyfluorfen
benoxacor


B-248
saflufenacil
benoxacor


B-249
sulfentrazone
benoxacor


B-250
H-1
benoxacor


B-251
H-2
benoxacor


B-252
glyphosate
benoxacor


B-253
glyphosate-isopropylammonium
benoxacor


B-254
glyphosate-trimesium (sulfosate)
benoxacor


B-255
glufosinate
benoxacor


B-256
glufosinate-ammonium
benoxacor


B-257
pendimethalin
benoxacor


B-258
trifluralin
benoxacor


B-259
acetochlor
benoxacor


B-260
cafenstrole
benoxacor


B-261
dimethenamid-P
benoxacor


B-262
fentrazamide
benoxacor


B-263
flufenacet
benoxacor


B-264
mefenacet
benoxacor


B-265
metazachlor
benoxacor


B-266
metolachlor-S
benoxacor


B-267
pyroxasulfone
benoxacor


B-268
isoxaben
benoxacor


B-269
dymron
benoxacor


B-270
indanofan
benoxacor


B-271
oxaziclomefone
benoxacor


B-272
triaziflam
benoxacor


B-273
atrazine + H-1
benoxacor


B-274
atrazine + glyphosate
benoxacor


B-275
atrazine + mesotrione
benoxacor


B-276
atrazine + nicosulfuron
benoxacor


B-277
atrazine + tembotrione
benoxacor


B-278
atrazine + topramezone
benoxacor


B-279
clomazone + glyphosate
benoxacor


B-280
diflufenican + clodinafop-propargyl
benoxacor


B-281
diflufenican + fenoxaprop-P-ethyl
benoxacor


B-282
diflufenican + flupyrsulfuron-methyl-sodium
benoxacor


B-283
diflufenican + glyphosate
benoxacor


B-284
diflufenican + mesosulfuron-methyl
benoxacor


B-285
diflufenican + pinoxaden
benoxacor


B-286
diflufenican + pyroxsulam
benoxacor


B-287
flumetsulam + glyphosate
benoxacor


B-288
flumioxazin + glyphosate
benoxacor


B-289
imazapic + glyphosate
benoxacor


B-290
imazethapyr + glyphosate
benoxacor


B-291
isoxaflutol + H-1
benoxacor


B-292
isoxaflutol + glyphosate
benoxacor


B-293
metazachlor + H-1
benoxacor


B-294
metazachlor + glyphosate
benoxacor


B-295
metazachlor + mesotrione
benoxacor


B-296
metazachlor + nicosulfuron
benoxacor


B-297
metazachlor + terbuthylazine
benoxacor


B-298
metazachlor + topramezone
benoxacor


B-299
metribuzin + glyphosate
benoxacor


B-300
pendimethalin + H-1
benoxacor


B-301
pendimethalin + clodinafop-propargyl
benoxacor


B-302
pendimethalin + fenoxaprop-P-ethyl
benoxacor


B-303
pendimethalin + flupyrsulfuron-methyl-sodium
benoxacor


B-304
pendimethalin + glyphosate
benoxacor


B-305
pendimethalin + mesosulfuron-methyl
benoxacor


B-306
pendimethalin + mesotrione
benoxacor


B-307
pendimethalin + nicosulfuron
benoxacor


B-308
pendimethalin + pinoxaden
benoxacor


B-309
pendimethalin + pyroxsulam
benoxacor


B-310
pendimethalin + tembotrione
benoxacor


B-311
pendimethalin + topramezone
benoxacor


B-312
pyroxasulfone + tembotrione
benoxacor


B-313
pyroxasulfone + topramezone
benoxacor


B-314
sulfentrazone + glyphosate
benoxacor


B-315
terbuthylazine + H-1
benoxacor


B-316
terbuthylazine + foramsulfuron
benoxacor


B-317
terbuthylazine + glyphosate
benoxacor


B-318
terbuthylazine + mesotrione
benoxacor


B-319
terbuthylazine + nicosulfuron
benoxacor


B-320
terbuthylazine + tembotrione
benoxacor


B-321
terbuthylazine + topramezone
benoxacor


B-322
trifluralin + glyphosate
benoxacor


B-323
clodinafop-propargyl
cloquintocet


B-324
cycloxydim
cloquintocet


B-325
cyhalofop-butyl
cloquintocet


B-326
fenoxaprop-P-ethyl
cloquintocet


B-327
pinoxaden
cloquintocet


B-328
profoxydim
cloquintocet


B-329
tepraloxydim
cloquintocet


B-330
tralkoxydim
cloquintocet


B-331
esprocarb
cloquintocet


B-332
prosulfocarb
cloquintocet


B-333
thiobencarb
cloquintocet


B-334
triallate
cloquintocet


B-335
bensulfuron-methyl
cloquintocet


B-336
bispyribac-sodium
cloquintocet


B-337
cyclosulfamuron
cloquintocet


B-338
flumetsulam
cloquintocet


B-339
flupyrsulfuron-methyl-sodium
cloquintocet


B-340
foramsulfuron
cloquintocet


B-341
imazamox
cloquintocet


B-342
imazapic
cloquintocet


B-343
imazapyr
cloquintocet


B-344
imazaquin
cloquintocet


B-345
imazethapyr
cloquintocet


B-346
imazosulfuron
cloquintocet


B-347
iodosulfuron-methyl-sodium
cloquintocet


B-348
mesosulfuron
cloquintocet


B-349
nicosulfuron
cloquintocet


B-350
penoxsulam
cloquintocet


B-351
propoxycarbazone-sodium
cloquintocet


B-352
pyrazosulfuron-ethyl
cloquintocet


B-353
pyroxsulam
cloquintocet


B-354
rimsulfuron
cloquintocet


B-355
sulfosulfuron
cloquintocet


B-356
thiencarbazone-methyl
cloquintocet


B-357
tritosulfuron
cloquintocet


B-358
2,4-D and its salts and esters
cloquintocet


B-359
aminopyralid and its salts and esters
cloquintocet


B-360
clopyralid and its salts and esters
cloquintocet


B-361
dicamba and its salts and esters
cloquintocet


B-362
fluroxypyr-meptyl
cloquintocet


B-363
quinclorac
cloquintocet


B-364
quinmerac
cloquintocet


B-365
H-9
cloquintocet


B-366
diflufenzopyr
cloquintocet


B-367
diflufenzopyr-sodium
cloquintocet


B-368
clomazone
cloquintocet


B-369
diflufenican
cloquintocet


B-370
fluorochloridone
cloquintocet


B-371
isoxaflutol
cloquintocet


B-372
mesotrione
cloquintocet


B-373
picolinafen
cloquintocet


B-374
sulcotrione
cloquintocet


B-375
tefuryltrione
cloquintocet


B-376
tembotrione
cloquintocet


B-377
topramezone
cloquintocet


B-378
H-7
cloquintocet


B-379
atrazine
cloquintocet


B-380
diuron
cloquintocet


B-381
fluometuron
cloquintocet


B-382
hexazinone
cloquintocet


B-383
isoproturon
cloquintocet


B-384
metribuzin
cloquintocet


B-385
propanil
cloquintocet


B-386
terbuthylazine
cloquintocet


B-387
paraquat dichloride
cloquintocet


B-388
flumioxazin
cloquintocet


B-389
oxyfluorfen
cloquintocet


B-390
saflufenacil
cloquintocet


B-391
sulfentrazone
cloquintocet


B-392
H-1
cloquintocet


B-393
H-2
cloquintocet


B-394
glyphosate
cloquintocet


B-395
glyphosate-isopropylammonium
cloquintocet


B-396
glyphosate-trimesium (sulfosate)
cloquintocet


B-397
glufosinate
cloquintocet


B-398
glufosinate-ammonium
cloquintocet


B-399
pendimethalin
cloquintocet


B-400
trifluralin
cloquintocet


B-401
acetochlor
cloquintocet


B-402
cafenstrole
cloquintocet


B-403
dimethenamid-P
cloquintocet


B-404
fentrazamide
cloquintocet


B-405
flufenacet
cloquintocet


B-406
mefenacet
cloquintocet


B-407
metazachlor
cloquintocet


B-408
metolachlor-S
cloquintocet


B-409
pyroxasulfone
cloquintocet


B-410
isoxaben
cloquintocet


B-411
dymron
cloquintocet


B-412
indanofan
cloquintocet


B-413
oxaziclomefone
cloquintocet


B-414
triaziflam
cloquintocet


B-415
atrazine + H-1
cloquintocet


B-416
atrazine + glyphosate
cloquintocet


B-417
atrazine + mesotrione
cloquintocet


B-418
atrazine + nicosulfuron
cloquintocet


B-419
atrazine + tembotrione
cloquintocet


B-420
atrazine + topramezone
cloquintocet


B-421
clomazone + glyphosate
cloquintocet


B-422
diflufenican + clodinafop-propargyl
cloquintocet


B-423
diflufenican + fenoxaprop-p-ethyl
cloquintocet


B-424
diflufenican + flupyrsulfuron-methyl-sodium
cloquintocet


B-425
diflufenican + glyphosate
cloquintocet


B-426
diflufenican + mesosulfuron-methyl
cloquintocet


B-427
diflufenican + pinoxaden
cloquintocet


B-428
diflufenican + pyroxsulam
cloquintocet


B-429
flumetsulam + glyphosate
cloquintocet


B-430
flumioxazin + glyphosate
cloquintocet


B-431
imazapic + glyphosate
cloquintocet


B-432
imazethapyr + glyphosate
cloquintocet


B-433
isoxaflutol + H-1
cloquintocet


B-434
isoxaflutol + glyphosate
cloquintocet


B-435
metazachlor + H-1
cloquintocet


B-436
metazachlor + glyphosate
cloquintocet


B-437
metazachlor + mesotrione
cloquintocet


B-438
metazachlor + nicosulfuron
cloquintocet


B-439
metazachlor + terbuthylazine
cloquintocet


B-440
metazachlor + topramezone
cloquintocet


B-441
metribuzin + glyphosate
cloquintocet


B-442
pendimethalin + H-1
cloquintocet


B-443
pendimethalin + clodinafop-propargyl
cloquintocet


B-444
pendimethalin + fenoxaprop-P-ethyl
cloquintocet


B-445
pendimethalin + flupyrsulfuron-methyl-sodium
cloquintocet


B-446
pendimethalin + glyphosate
cloquintocet


B-447
pendimethalin + mesosulfuron-methyl
cloquintocet


B-448
pendimethalin + mesotrione
cloquintocet


B-449
pendimethalin + nicosulfuron
cloquintocet


B-450
pendimethalin + pinoxaden
cloquintocet


B-451
pendimethalin + pyroxsulam
cloquintocet


B-452
pendimethalin + tembotrione
cloquintocet


B-453
pendimethalin + topramezone
cloquintocet


B-454
pyroxasulfone + tembotrione
cloquintocet


B-455
pyroxasulfone + topramezone
cloquintocet


B-456
sulfentrazone + glyphosate
cloquintocet


B-457
terbuthylazine + H-1
cloquintocet


B-458
terbuthylazine + foramsulfuron
cloquintocet


B-459
terbuthylazine + glyphosate
cloquintocet


B-460
terbuthylazine + mesotrione
cloquintocet


B-461
terbuthylazine + nicosulfuron
cloquintocet


B-462
terbuthylazine + tembotrione
cloquintocet


B-463
terbuthylazine + topramezone
cloquintocet


B-464
trifluralin + glyphosate
cloquintocet


B-465
clodinafop-propargyl
dichlormid


B-466
cycloxydim
dichlormid


B-467
cyhalofop-butyl
dichlormid


B-468
fenoxaprop-P-ethyl
dichlormid


B-469
pinoxaden
dichlormid


B-470
profoxydim
dichlormid


B-471
tepraloxydim
dichlormid


B-472
tralkoxydim
dichlormid


B-473
esprocarb
dichlormid


B-474
prosulfocarb
dichlormid


B-475
thiobencarb
dichlormid


B-476
triallate
dichlormid


B-477
bensulfuron-methyl
dichlormid


B-478
bispyribac-sodium
dichlormid


B-479
cyclosulfamuron
dichlormid


B-480
flumetsulam
dichlormid


B-481
flupyrsulfuron-methyl-sodium
dichlormid


B-482
foramsulfuron
dichlormid


B-483
imazamox
dichlormid


B-484
imazapic
dichlormid


B-485
imazapyr
dichlormid


B-486
imazaquin
dichlormid


B-487
imazethapyr
dichlormid


B-488
imazosulfuron
dichlormid


B-489
iodosulfuron-methyl-sodium
dichlormid


B-490
mesosulfuron
dichlormid


B-491
nicosulfuron
dichlormid


B-492
penoxsulam
dichlormid


B-493
propoxycarbazone-sodium
dichlormid


B-494
pyrazosulfuron-ethyl
dichlormid


B-495
pyroxsulam
dichlormid


B-496
rimsulfuron
dichlormid


B-497
sulfosulfuron
dichlormid


B-498
thiencarbazone-methyl
dichlormid


B-499
tritosulfuron
dichlormid


B-500
2,4-D and its salts and esters
dichlormid


B-501
aminopyralid and its salts and esters
dichlormid


B-502
clopyralid and its salts and esters
dichlormid


B-503
dicamba and its salts and esters
dichlormid


B-504
fluroxypyr-meptyl
dichlormid


B-505
quinclorac
dichlormid


B-506
quinmerac
dichlormid


B-507
H-9
dichlormid


B-508
diflufenzopyr
dichlormid


B-509
diflufenzopyr-sodium
dichlormid


B-510
clomazone
dichlormid


B-511
diflufenican
dichlormid


B-512
fluorochloridone
dichlormid


B-513
isoxaflutol
dichlormid


B-514
mesotrione
dichlormid


B-515
picolinafen
dichlormid


B-516
sulcotrione
dichlormid


B-517
tefuryltrione
dichlormid


B-518
tembotrione
dichlormid


B-519
topramezone
dichlormid


B-520
H-7
dichlormid


B-521
atrazine
dichlormid


B-522
diuron
dichlormid


B-523
fluometuron
dichlormid


B-524
hexazinone
dichlormid


B-525
isoproturon
dichlormid


B-526
metribuzin
dichlormid


B-527
propanil
dichlormid


B-528
terbuthylazine
dichlormid


B-529
paraquat dichloride
dichlormid


B-530
flumioxazin
dichlormid


B-531
oxyfluorfen
dichlormid


B-532
saflufenacil
dichlormid


B-533
sulfentrazone
dichlormid


B-534
H-1
dichlormid


B-535
H-2
dichlormid


B-536
glyphosate
dichlormid


B-537
glyphosate-isopropylammonium
dichlormid


B-538
glyphosate-trimesium (sulfosate)
dichlormid


B-539
glufosinate
dichlormid


B-540
glufosinate-ammonium
dichlormid


B-541
pendimethalin
dichlormid


B-542
trifluralin
dichlormid


B-543
acetochlor
dichlormid


B-544
cafenstrole
dichlormid


B-545
dimethenamid-P
dichlormid


B-546
fentrazamide
dichlormid


B-547
flufenacet
dichlormid


B-548
mefenacet
dichlormid


B-549
metazachlor
dichlormid


B-550
metolachlor-S
dichlormid


B-551
pyroxasulfone
dichlormid


B-552
isoxaben
dichlormid


B-553
dymron
dichlormid


B-554
indanofan
dichlormid


B-555
oxaziclomefone
dichlormid


B-556
triaziflam
dichlormid


B-557
atrazine + H-1
dichlormid


B-558
atrazine + glyphosate
dichlormid


B-559
atrazine + mesotrione
dichlormid


B-560
atrazine + nicosulfuron
dichlormid


B-561
atrazine + tembotrione
dichlormid


B-562
atrazine + topramezone
dichlormid


B-563
clomazone + glyphosate
dichlormid


B-564
diflufenican + clodinafop-propargyl
dichlormid


B-565
diflufenican + fenoxaprop-p-ethyl
dichlormid


B-566
diflufenican + flupyrsulfuron-methyl-sodium
dichlormid


B-567
diflufenican + glyphosate
dichlormid


B-568
diflufenican + mesosulfuron-methyl
dichlormid


B-569
diflufenican + pinoxaden
dichlormid


B-570
diflufenican + pyroxsulam
dichlormid


B-571
flumetsulam + glyphosate
dichlormid


B-572
flumioxazin + glyphosate
dichlormid


B-573
imazapic + glyphosate
dichlormid


B-574
imazethapyr + glyphosate
dichlormid


B-575
isoxaflutol + H-1
dichlormid


B-576
isoxaflutol + glyphosate
dichlormid


B-577
metazachlor + H-1
dichlormid


B-578
metazachlor + glyphosate
dichlormid


B-579
metazachlor + mesotrione
dichlormid


B-580
metazachlor + nicosulfuron
dichlormid


B-581
metazachlor + terbuthylazine
dichlormid


B-582
metazachlor + topramezone
dichlormid


B-583
metribuzin + glyphosate
dichlormid


B-584
pendimethalin + H-1
dichlormid


B-585
pendimethalin + clodinafop-propargyl
dichlormid


B-586
pendimethalin + fenoxaprop-P-ethyl
dichlormid


B-587
pendimethalin + flupyrsulfuron-methyl-sodium
dichlormid


B-588
pendimethalin + glyphosate
dichlormid


B-589
pendimethalin + mesosulfuron-methyl
dichlormid


B-590
pendimethalin + mesotrione
dichlormid


B-591
pendimethalin + nicosulfuron
dichlormid


B-592
pendimethalin + pinoxaden
dichlormid


B-593
pendimethalin + pyroxsulam
dichlormid


B-594
pendimethalin + tembotrione
dichlormid


B-595
pendimethalin + topramezone
dichlormid


B-596
pyroxasulfone + tembotrione
dichlormid


B-597
pyroxasulfone + topramezone
dichlormid


B-598
sulfentrazone + glyphosate
dichlormid


B-599
terbuthylazine + H-1
dichlormid


B-600
terbuthylazine + foramsulfuron
dichlormid


B-601
terbuthylazine + glyphosate
dichlormid


B-602
terbuthylazine + mesotrione
dichlormid


B-603
terbuthylazine + nicosulfuron
dichlormid


B-604
terbuthylazine + tembotrione
dichlormid


B-605
terbuthylazine + topramezone
dichlormid


B-606
trifluralin + glyphosate
dichlormid


B-607
clodinafop-propargyl
fenchlorazole


B-608
cycloxydim
fenchlorazole


B-609
cyhalofop-butyl
fenchlorazole


B-610
fenoxaprop-P-ethyl
fenchlorazole


B-611
pinoxaden
fenchlorazole


B-612
profoxydim
fenchlorazole


B-613
tepraloxydim
fenchlorazole


B-614
tralkoxydim
fenchlorazole


B-615
esprocarb
fenchlorazole


B-616
prosulfocarb
fenchlorazole


B-617
thiobencarb
fenchlorazole


B-618
triallate
fenchlorazole


B-619
bensulfuron-methyl
fenchlorazole


B-620
bispyribac-sodium
fenchlorazole


B-621
cyclosulfamuron
fenchlorazole


B-622
flumetsulam
fenchlorazole


B-623
flupyrsulfuron-methyl-sodium
fenchlorazole


B-624
foramsulfuron
fenchlorazole


B-625
imazamox
fenchlorazole


B-626
imazapic
fenchlorazole


B-627
imazapyr
fenchlorazole


B-628
imazaquin
fenchlorazole


B-629
imazethapyr
fenchlorazole


B-630
imazosulfuron
fenchlorazole


B-631
iodosulfuron-methyl-sodium
fenchlorazole


B-632
mesosulfuron
fenchlorazole


B-633
nicosulfuron
fenchlorazole


B-634
penoxsulam
fenchlorazole


B-635
propoxycarbazone-sodium
fenchlorazole


B-636
pyrazosulfuron-ethyl
fenchlorazole


B-637
pyroxsulam
fenchlorazole


B-638
rimsulfuron
fenchlorazole


B-639
sulfosulfuron
fenchlorazole


B-640
thiencarbazone-methyl
fenchlorazole


B-641
tritosulfuron
fenchlorazole


B-642
2,4-D and its salts and esters
fenchlorazole


B-643
aminopyralid and its salts and esters
fenchlorazole


B-644
clopyralid and its salts and esters
fenchlorazole


B-645
dicamba and its salts and esters
fenchlorazole


B-646
fluroxypyr-meptyl
fenchlorazole


B-647
quinclorac
fenchlorazole


B-648
quinmerac
fenchlorazole


B-649
H-9
fenchlorazole


B-650
diflufenzopyr
fenchlorazole


B-651
diflufenzopyr-sodium
fenchlorazole


B-652
clomazone
fenchlorazole


B-653
diflufenican
fenchlorazole


B-654
fluorochloridone
fenchlorazole


B-655
isoxaflutol
fenchlorazole


B-656
mesotrione
fenchlorazole


B-657
picolinafen
fenchlorazole


B-658
sulcotrione
fenchlorazole


B-659
tefuryltrione
fenchlorazole


B-660
tembotrione
fenchlorazole


B-661
topramezone
fenchlorazole


B-662
H-7
fenchlorazole


B-663
atrazine
fenchlorazole


B-664
diuron
fenchlorazole


B-665
fluometuron
fenchlorazole


B-666
hexazinone
fenchlorazole


B-667
isoproturon
fenchlorazole


B-668
metribuzin
fenchlorazole


B-669
propanil
fenchlorazole


B-670
terbuthylazine
fenchlorazole


B-671
paraquat dichloride
fenchlorazole


B-672
flumioxazin
fenchlorazole


B-673
oxyfluorfen
fenchlorazole


B-674
saflufenacil
fenchlorazole


B-675
sulfentrazone
fenchlorazole


B-676
H-1
fenchlorazole


B-677
H-2
fenchlorazole


B-678
glyphosate
fenchlorazole


B-679
glyphosate-isopropylammonium
fenchlorazole


B-680
glyphosate-trimesium (sulfosate)
fenchlorazole


B-681
glufosinate
fenchlorazole


B-682
glufosinate-ammonium
fenchlorazole


B-683
pendimethalin
fenchlorazole


B-684
trifluralin
fenchlorazole


B-685
acetochlor
fenchlorazole


B-686
cafenstrole
fenchlorazole


B-687
dimethenamid-P
fenchlorazole


B-688
fentrazamide
fenchlorazole


B-689
flufenacet
fenchlorazole


B-690
mefenacet
fenchlorazole


B-691
metazachlor
fenchlorazole


B-692
metolachlor-S
fenchlorazole


B-693
pyroxasulfone
fenchlorazole


B-694
isoxaben
fenchlorazole


B-695
dymron
fenchlorazole


B-696
indanofan
fenchlorazole


B-697
oxaziclomefone
fenchlorazole


B-698
triaziflam
fenchlorazole


B-699
atrazine + H-1
fenchlorazole


B-700
atrazine + glyphosate
fenchlorazole


B-701
atrazine + mesotrione
fenchlorazole


B-702
atrazine + nicosulfuron
fenchlorazole


B-703
atrazine + tembotrione
fenchlorazole


B-704
atrazine + topramezone
fenchlorazole


B-705
clomazone + glyphosate
fenchlorazole


B-706
diflufenican + clodinafop-propargyl
fenchlorazole


B-707
diflufenican + fenoxaprop-P-ethyl
fenchlorazole


B-708
diflufenican + flupyrsulfuron-methyl-sodium
fenchlorazole


B-709
diflufenican + glyphosate
fenchlorazole


B-710
diflufenican + mesosulfuron-methyl
fenchlorazole


B-711
diflufenican + pinoxaden
fenchlorazole


B-712
diflufenican + pyroxsulam
fenchlorazole


B-713
flumetsulam + glyphosate
fenchlorazole


B-714
flumioxazin + glyphosate
fenchlorazole


B-715
imazapic + glyphosate
fenchlorazole


B-716
imazethapyr + glyphosate
fenchlorazole


B-717
isoxaflutol + H-1
fenchlorazole


B-718
isoxaflutol + glyphosate
fenchlorazole


B-719
metazachlor + H-1
fenchlorazole


B-720
metazachlor + glyphosate
fenchlorazole


B-721
metazachlor + mesotrione
fenchlorazole


B-722
metazachlor + nicosulfuron
fenchlorazole


B-723
metazachlor + terbuthylazine
fenchlorazole


B-724
metazachlor + topramezone
fenchlorazole


B-725
metribuzin + glyphosate
fenchlorazole


B-726
pendimethalin + H-1
fenchlorazole


B-727
pendimethalin + clodinafop-propargyl
fenchlorazole


B-728
pendimethalin + fenoxaprop-P-ethyl
fenchlorazole


B-729
pendimethalin + flupyrsulfuron-methyl-sodium
fenchlorazole


B-730
pendimethalin + glyphosate
fenchlorazole


B-731
pendimethalin + mesosulfuron-methyl
fenchlorazole


B-732
pendimethalin + mesotrione
fenchlorazole


B-733
pendimethalin + nicosulfuron
fenchlorazole


B-734
pendimethalin + pinoxaden
fenchlorazole


B-735
pendimethalin + pyroxsulam
fenchlorazole


B-736
pendimethalin + tembotrione
fenchlorazole


B-737
pendimethalin + topramezone
fenchlorazole


B-738
pyroxasulfone + tembotrione
fenchlorazole


B-739
pyroxasulfone + topramezone
fenchlorazole


B-740
sulfentrazone + glyphosate
fenchlorazole


B-741
terbuthylazine + H-1
fenchlorazole


B-742
terbuthylazine + foramsulfuron
fenchlorazole


B-743
terbuthylazine + glyphosate
fenchlorazole


B-744
terbuthylazine + mesotrione
fenchlorazole


B-745
terbuthylazine + nicosulfuron
fenchlorazole


B-746
terbuthylazine + tembotrione
fenchlorazole


B-747
terbuthylazine + topramezone
fenchlorazole


B-748
trifluralin + glyphosate
fenchlorazole


B-749
clodinafop-propargyl
fenclorim


B-750
cycloxydim
fenclorim


B-751
cyhalofop-butyl
fenclorim


B-752
fenoxaprop-P-ethyl
fenclorim


B-753
pinoxaden
fenclorim


B-754
profoxydim
fenclorim


B-755
tepraloxydim
fenclorim


B-756
tralkoxydim
fenclorim


B-757
esprocarb
fenclorim


B-758
prosulfocarb
fenclorim


B-759
thiobencarb
fenclorim


B-760
triallate
fenclorim


B-761
bensulfuron-methyl
fenclorim


B-762
bispyribac-sodium
fenclorim


B-763
cyclosulfamuron
fenclorim


B-764
flumetsulam
fenclorim


B-765
flupyrsulfuron-methyl-sodium
fenclorim


B-766
foramsulfuron
fenclorim


B-767
imazamox
fenclorim


B-768
imazapic
fenclorim


B-769
imazapyr
fenclorim


B-770
imazaquin
fenclorim


B-771
imazethapyr
fenclorim


B-772
imazosulfuron
fenclorim


B-773
iodosulfuron-methyl-sodium
fenclorim


B-774
mesosulfuron
fenclorim


B-775
nicosulfuron
fenclorim


B-776
penoxsulam
fenclorim


B-777
propoxycarbazone-sodium
fenclorim


B-778
pyrazosulfuron-ethyl
fenclorim


B-779
pyroxsulam
fenclorim


B-780
rimsulfuron
fenclorim


B-781
sulfosulfuron
fenclorim


B-782
thiencarbazone-methyl
fenclorim


B-783
tritosulfuron
fenclorim


B-784
2,4-D and its salts and esters
fenclorim


B-785
aminopyralid and its salts and esters
fenclorim


B-786
clopyralid and its salts and esters
fenclorim


B-787
dicamba and its salts and esters
fenclorim


B-788
fluroxypyr-meptyl
fenclorim


B-789
quinclorac
fenclorim


B-790
quinmerac
fenclorim


B-791
H-9
fenclorim


B-792
diflufenzopyr
fenclorim


B-793
diflufenzopyr-sodium
fenclorim


B-794
clomazone
fenclorim


B-795
diflufenican
fenclorim


B-796
fluorochloridone
fenclorim


B-797
isoxaflutol
fenclorim


B-798
mesotrione
fenclorim


B-799
picolinafen
fenclorim


B-800
sulcotrione
fenclorim


B-801
tefuryltrione
fenclorim


B-802
tembotrione
fenclorim


B-803
topramezone
fenclorim


B-804
H-7
fenclorim


B-805
atrazine
fenclorim


B-806
diuron
fenclorim


B-807
fluometuron
fenclorim


B-808
hexazinone
fenclorim


B-809
isoproturon
fenclorim


B-810
metribuzin
fenclorim


B-811
propanil
fenclorim


B-812
terbuthylazine
fenclorim


B-813
paraquat dichloride
fenclorim


B-814
flumioxazin
fenclorim


B-815
oxyfluorfen
fenclorim


B-816
saflufenacil
fenclorim


B-817
sulfentrazone
fenclorim


B-818
H-1
fenclorim


B-819
H-2
fenclorim


B-820
glyphosate
fenclorim


B-821
glyphosate-isopropylammonium
fenclorim


B-822
glyphosate-trimesium (sulfosate)
fenclorim


B-823
glufosinate
fenclorim


B-824
glufosinate-ammonium
fenclorim


B-825
pendimethalin
fenclorim


B-826
trifluralin
fenclorim


B-827
acetochlor
fenclorim


B-828
cafenstrole
fenclorim


B-829
dimethenamid-P
fenclorim


B-830
fentrazamide
fenclorim


B-831
flufenacet
fenclorim


B-832
mefenacet
fenclorim


B-833
metazachlor
fenclorim


B-834
metolachlor-S
fenclorim


B-835
pyroxasulfone
fenclorim


B-836
isoxaben
fenclorim


B-837
dymron
fenclorim


B-838
indanofan
fenclorim


B-839
oxaziclomefone
fenclorim


B-840
triaziflam
fenclorim


B-841
atrazine + H-1
fenclorim


B-842
atrazine + glyphosate
fenclorim


B-843
atrazine + mesotrione
fenclorim


B-844
atrazine + nicosulfuron
fenclorim


B-845
atrazine + tembotrione
fenclorim


B-846
atrazine + topramezone
fenclorim


B-847
clomazone + glyphosate
fenclorim


B-848
diflufenican + clodinafop-propargyl
fenclorim


B-849
diflufenican + fenoxaprop-P-ethyl
fenclorim


B-850
diflufenican + flupyrsulfuron-methyl-sodium
fenclorim


B-851
diflufenican + glyphosate
fenclorim


B-852
diflufenican + mesosulfuron-methyl
fenclorim


B-853
diflufenican + pinoxaden
fenclorim


B-854
diflufenican + pyroxsulam
fenclorim


B-855
flumetsulam + glyphosate
fenclorim


B-856
flumioxazin + glyphosate
fenclorim


B-857
imazapic + glyphosate
fenclorim


B-858
imazethapyr + glyphosate
fenclorim


B-859
isoxaflutol + H-1
fenclorim


B-860
isoxaflutol + glyphosate
fenclorim


B-861
metazachlor + H-1
fenclorim


B-862
metazachlor + glyphosate
fenclorim


B-863
metazachlor + mesotrione
fenclorim


B-864
metazachlor + nicosulfuron
fenclorim


B-865
metazachlor + terbuthylazine
fenclorim


B-866
metazachlor + topramezone
fenclorim


B-867
metribuzin + glyphosate
fenclorim


B-868
pendimethalin + H-1
fenclorim


B-869
pendimethalin + clodinafop-propargyl
fenclorim


B-870
pendimethalin + fenoxaprop-P-ethyl
fenclorim


B-871
pendimethalin + flupyrsulfuron-methyl-sodium
fenclorim


B-872
pendimethalin + glyphosate
fenclorim


B-873
pendimethalin + mesosulfuron-methyl
fenclorim


B-874
pendimethalin + mesotrione
fenclorim


B-875
pendimethalin + nicosulfuron
fenclorim


B-876
pendimethalin + pinoxaden
fenclorim


B-877
pendimethalin + pyroxsulam
fenclorim


B-878
pendimethalin + tembotrione
fenclorim


B-879
pendimethalin + topramezone
fenclorim


B-880
pyroxasulfone + tembotrione
fenclorim


B-881
pyroxasulfone + topramezone
fenclorim


B-882
sulfentrazone + glyphosate
fenclorim


B-883
terbuthylazine + H-1
fenclorim


B-884
terbuthylazine + foramsulfuron
fenclorim


B-885
terbuthylazine + glyphosate
fenclorim


B-886
terbuthylazine + mesotrione
fenclorim


B-887
terbuthylazine + nicosulfuron
fenclorim


B-888
terbuthylazine + tembotrione
fenclorim


B-889
terbuthylazine + topramezone
fenclorim


B-890
trifluralin + glyphosate
fenclorim


B-891
clodinafop-propargyl
isoxadifen


B-892
cycloxydim
isoxadifen


B-893
cyhalofop-butyl
isoxadifen


B-894
fenoxaprop-P-ethyl
isoxadifen


B-895
pinoxaden
isoxadifen


B-896
profoxydim
isoxadifen


B-897
tepraloxydim
isoxadifen


B-898
tralkoxydim
isoxadifen


B-899
esprocarb
isoxadifen


B-900
prosulfocarb
isoxadifen


B-901
thiobencarb
isoxadifen


B-902
triallate
isoxadifen


B-903
bensulfuron-methyl
isoxadifen


B-904
bispyribac-sodium
isoxadifen


B-905
cyclosulfamuron
isoxadifen


B-906
flumetsulam
isoxadifen


B-907
flupyrsulfuron-methyl-sodium
isoxadifen


B-908
foramsulfuron
isoxadifen


B-909
imazamox
isoxadifen


B-910
imazapic
isoxadifen


B-911
imazapyr
isoxadifen


B-912
imazaquin
isoxadifen


B-913
imazethapyr
isoxadifen


B-914
imazosulfuron
isoxadifen


B-915
iodosulfuron-methyl-sodium
isoxadifen


B-916
mesosulfuron
isoxadifen


B-917
nicosulfuron
isoxadifen


B-918
penoxsulam
isoxadifen


B-919
propoxycarbazone-sodium
isoxadifen


B-920
pyrazosulfuron-ethyl
isoxadifen


B-921
pyroxsulam
isoxadifen


B-922
rimsulfuron
isoxadifen


B-923
sulfosulfuron
isoxadifen


B-924
thiencarbazone-methyl
isoxadifen


B-925
tritosulfuron
isoxadifen


B-926
2,4-D and its salts and esters
isoxadifen


B-927
aminopyralid and its salts and esters
isoxadifen


B-928
clopyralid and its salts and esters
isoxadifen


B-929
dicamba and its salts and esters
isoxadifen


B-930
fluroxypyr-meptyl
isoxadifen


B-931
quinclorac
isoxadifen


B-932
quinmerac
isoxadifen


B-933
H-9
isoxadifen


B-934
diflufenzopyr
isoxadifen


B-935
diflufenzopyr-sodium
isoxadifen


B-936
clomazone
isoxadifen


B-937
diflufenican
isoxadifen


B-938
fluorochloridone
isoxadifen


B-939
isoxaflutol
isoxadifen


B-940
mesotrione
isoxadifen


B-941
picolinafen
isoxadifen


B-942
sulcotrione
isoxadifen


B-943
tefuryltrione
isoxadifen


B-944
tembotrione
isoxadifen


B-945
topramezone
isoxadifen


B-946
H-7
isoxadifen


B-947
atrazine
isoxadifen


B-948
diuron
isoxadifen


B-949
fluometuron
isoxadifen


B-950
hexazinone
isoxadifen


B-951
isoproturon
isoxadifen


B-952
metribuzin
isoxadifen


B-953
propanil
isoxadifen


B-954
terbuthylazine
isoxadifen


B-955
paraquat dichloride
isoxadifen


B-956
flumioxazin
isoxadifen


B-957
oxyfluorfen
isoxadifen


B-958
saflufenacil
isoxadifen


B-959
sulfentrazone
isoxadifen


B-960
H-1
isoxadifen


B-961
H-2
isoxadifen


B-962
glyphosate
isoxadifen


B-963
glyphosate-isopropylammonium
isoxadifen


B-964
glyphosate-trimesium (sulfosate)
isoxadifen


B-965
glufosinate
isoxadifen


B-966
glufosinate-ammonium
isoxadifen


B-967
pendimethalin
isoxadifen


B-968
trifluralin
isoxadifen


B-969
acetochlor
isoxadifen


B-970
cafenstrole
isoxadifen


B-971
dimethenamid-P
isoxadifen


B-972
fentrazamide
isoxadifen


B-973
flufenacet
isoxadifen


B-974
mefenacet
isoxadifen


B-975
metazachlor
isoxadifen


B-976
metolachlor-S
isoxadifen


B-977
pyroxasulfone
isoxadifen


B-978
isoxaben
isoxadifen


B-979
dymron
isoxadifen


B-980
indanofan
isoxadifen


B-981
oxaziclomefone
isoxadifen


B-982
triaziflam
isoxadifen


B-983
atrazine + H-1
isoxadifen


B-984
atrazine + glyphosate
isoxadifen


B-985
atrazine + mesotrione
isoxadifen


B-986
atrazine + nicosulfuron
isoxadifen


B-987
atrazine + tembotrione
isoxadifen


B-988
atrazine + topramezone
isoxadifen


B-989
clomazone + glyphosate
isoxadifen


B-990
diflufenican + clodinafop-propargyl
isoxadifen


B-991
diflufenican + fenoxaprop-P-ethyl
isoxadifen


B-992
diflufenican + flupyrsulfuron-methyl-sodium
isoxadifen


B-993
diflufenican + glyphosate
isoxadifen


B-994
diflufenican + mesosulfuron-methyl
isoxadifen


B-995
diflufenican + pinoxaden
isoxadifen


B-996
diflufenican + pyroxsulam
isoxadifen


B-997
flumetsulam + glyphosate
isoxadifen


B-998
flumioxazin + glyphosate
isoxadifen


B-999
imazapic + glyphosate
isoxadifen


B-1000
imazethapyr + glyphosate
isoxadifen


B-1001
isoxaflutol + H-1
isoxadifen


B-1002
isoxaflutol + glyphosate
isoxadifen


B-1003
metazachlor + H-1
isoxadifen


B-1004
metazachlor + glyphosate
isoxadifen


B-1005
metazachlor + mesotrione
isoxadifen


B-1006
metazachlor + nicosulfuron
isoxadifen


B-1007
metazachlor + terbuthylazine
isoxadifen


B-1008
metazachlor + topramezone
isoxadifen


B-1009
metribuzin + glyphosate
isoxadifen


B-1010
pendimethalin + H-1
isoxadifen


B-1011
pendimethalin + clodinafop-propargyl
isoxadifen


B-1012
pendimethalin + fenoxaprop-P-ethyl
isoxadifen


B-1013
pendimethalin + flupyrsulfuron-methyl-sodium
isoxadifen


B-1014
pendimethalin + glyphosate
isoxadifen


B-1015
pendimethalin + mesosulfuron-methyl
isoxadifen


B-1016
pendimethalin + mesotrione
isoxadifen


B-1017
pendimethalin + nicosulfuron
isoxadifen


B-1018
pendimethalin + pinoxaden
isoxadifen


B-1019
pendimethalin + pyroxsulam
isoxadifen


B-1020
pendimethalin + tembotrione
isoxadifen


B-1021
pendimethalin + topramezone
isoxadifen


B-1022
pyroxasulfone + tembotrione
isoxadifen


B-1023
pyroxasulfone + topramezone
isoxadifen


B-1024
sulfentrazone + glyphosate
isoxadifen


B-1025
terbuthylazine + H-1
isoxadifen


B-1026
terbuthylazine + foramsulfuron
isoxadifen


B-1027
terbuthylazine + glyphosate
isoxadifen


B-1028
terbuthylazine + mesotrione
isoxadifen


B-1029
terbuthylazine + nicosulfuron
isoxadifen


B-1030
terbuthylazine + tembotrione
isoxadifen


B-1031
terbuthylazine + topramezone
isoxadifen


B-1032
trifluralin + glyphosate
isoxadifen


B-1033
clodinafop-propargyl
mefenpyr


B-1034
cycloxydim
mefenpyr


B-1035
cyhalofop-butyl
mefenpyr


B-1036
fenoxaprop-P-ethyl
mefenpyr


B-1037
pinoxaden
mefenpyr


B-1038
profoxydim
mefenpyr


B-1039
tepraloxydim
mefenpyr


B-1040
tralkoxydim
mefenpyr


B-1041
esprocarb
mefenpyr


B-1042
prosulfocarb
mefenpyr


B-1043
thiobencarb
mefenpyr


B-1044
triallate
mefenpyr


B-1045
bensulfuron-methyl
mefenpyr


B-1046
bispyribac-sodium
mefenpyr


B-1047
cyclosulfamuron
mefenpyr


B-1048
flumetsulam
mefenpyr


B-1049
flupyrsulfuron-methyl-sodium
mefenpyr


B-1050
foramsulfuron
mefenpyr


B-1051
imazamox
mefenpyr


B-1052
imazapic
mefenpyr


B-1053
imazapyr
mefenpyr


B-1054
imazaquin
mefenpyr


B-1055
imazethapyr
mefenpyr


B-1056
imazosulfuron
mefenpyr


B-1057
iodosulfuron-methyl-sodium
mefenpyr


B-1058
mesosulfuron
mefenpyr


B-1059
nicosulfuron
mefenpyr


B-1060
penoxsulam
mefenpyr


B-1061
propoxycarbazone-sodium
mefenpyr


B-1062
pyrazosulfuron-ethyl
mefenpyr


B-1063
pyroxsulam
mefenpyr


B-1064
rimsulfuron
mefenpyr


B-1065
sulfosulfuron
mefenpyr


B-1066
thiencarbazone-methyl
mefenpyr


B-1067
tritosulfuron
mefenpyr


B-1068
2,4-D and its salts and esters
mefenpyr


B-1069
aminopyralid and its salts and esters
mefenpyr


B-1070
clopyralid and its salts and esters
mefenpyr


B-1071
dicamba and its salts and esters
mefenpyr


B-1072
fluroxypyr-meptyl
mefenpyr


B-1073
quinclorac
mefenpyr


B-1074
quinmerac
mefenpyr


B-1075
H-9
mefenpyr


B-1076
diflufenzopyr
mefenpyr


B-1077
diflufenzopyr-sodium
mefenpyr


B-1078
clomazone
mefenpyr


B-1079
diflufenican
mefenpyr


B-1080
fluorochloridone
mefenpyr


B-1081
isoxaflutol
mefenpyr


B-1082
mesotrione
mefenpyr


B-1083
picolinafen
mefenpyr


B-1084
sulcotrione
mefenpyr


B-1085
tefuryltrione
mefenpyr


B-1086
tembotrione
mefenpyr


B-1087
topramezone
mefenpyr


B-1088
H-7
mefenpyr


B-1089
atrazine
mefenpyr


B-1090
diuron
mefenpyr


B-1091
fluometuron
mefenpyr


B-1092
hexazinone
mefenpyr


B-1093
isoproturon
mefenpyr


B-1094
metribuzin
mefenpyr


B-1095
propanil
mefenpyr


B-1096
terbuthylazine
mefenpyr


B-1097
paraquat dichloride
mefenpyr


B-1098
flumioxazin
mefenpyr


B-1099
oxyfluorfen
mefenpyr


B-1100
saflufenacil
mefenpyr


B-1101
sulfentrazone
mefenpyr


B-1102
H-1
mefenpyr


B-1103
H-2
mefenpyr


B-1104
glyphosate
mefenpyr


B-1105
glyphosate-isopropylammonium
mefenpyr


B-1106
glyphosate-trimesium (sulfosate)
mefenpyr


B-1107
glufosinate
mefenpyr


B-1108
glufosinate-ammonium
mefenpyr


B-1109
pendimethalin
mefenpyr


B-1110
trifluralin
mefenpyr


B-1111
acetochlor
mefenpyr


B-1112
cafenstrole
mefenpyr


B-1113
dimethenamid-P
mefenpyr


B-1114
fentrazamide
mefenpyr


B-1115
flufenacet
mefenpyr


B-1116
mefenacet
mefenpyr


B-1117
metazachlor
mefenpyr


B-1118
metolachlor-S
mefenpyr


B-1119
pyroxasulfone
mefenpyr


B-1120
isoxaben
mefenpyr


B-1121
dymron
mefenpyr


B-1122
indanofan
mefenpyr


B-1123
oxaziclomefone
mefenpyr


B-1124
triaziflam
mefenpyr


B-1125
atrazine + H-1
mefenpyr


B-1126
atrazine + glyphosate
mefenpyr


B-1127
atrazine + mesotrione
mefenpyr


B-1128
atrazine + nicosulfuron
mefenpyr


B-1129
atrazine + tembotrione
mefenpyr


B-1130
atrazine + topramezone
mefenpyr


B-1131
clomazone + glyphosate
mefenpyr


B-1132
diflufenican + clodinafop-propargyl
mefenpyr


B-1133
diflufenican + fenoxaprop-P-ethyl
mefenpyr


B-1134
diflufenican + flupyrsulfuron-methyl-sodium
mefenpyr


B-1135
diflufenican + glyphosate
mefenpyr


B-1136
diflufenican + mesosulfuron-methyl
mefenpyr


B-1137
diflufenican + pinoxaden
mefenpyr


B-1138
diflufenican + pyroxsulam
mefenpyr


B-1139
flumetsulam + glyphosate
mefenpyr


B-1140
flumioxazin + glyphosate
mefenpyr


B-1141
imazapic + glyphosate
mefenpyr


B-1142
imazethapyr + glyphosate
mefenpyr


B-1143
isoxaflutol + H-1
mefenpyr


B-1144
isoxaflutol + glyphosate
mefenpyr


B-1145
metazachlor + H-1
mefenpyr


B-1146
metazachlor + glyphosate
mefenpyr


B-1147
metazachlor + mesotrione
mefenpyr


B-1148
metazachlor + nicosulfuron
mefenpyr


B-1149
metazachlor + terbuthylazine
mefenpyr


B-1150
metazachlor + topramezone
mefenpyr


B-1151
metribuzin + glyphosate
mefenpyr


B-1152
pendimethalin + H-1
mefenpyr


B-1153
pendimethalin + clodinafop-propargyl
mefenpyr


B-1154
pendimethalin + fenoxaprop-P-ethyl
mefenpyr


B-1155
pendimethalin + flupyrsulfuron-methyl-sodium
mefenpyr


B-1156
pendimethalin + glyphosate
mefenpyr


B-1157
pendimethalin + mesosulfuron-methyl
mefenpyr


B-1158
pendimethalin + mesotrione
mefenpyr


B-1159
pendimethalin + nicosulfuron
mefenpyr


B-1160
pendimethalin + pinoxaden
mefenpyr


B-1161
pendimethalin + pyroxsulam
mefenpyr


B-1162
pendimethalin + tembotrione
mefenpyr


B-1163
pendimethalin + topramezone
mefenpyr


B-1164
pyroxasulfone + tembotrione
mefenpyr


B-1165
pyroxasulfone + topramezone
mefenpyr


B-1166
sulfentrazone + glyphosate
mefenpyr


B-1167
terbuthylazine + H-1
mefenpyr


B-1168
terbuthylazine + foramsulfuron
mefenpyr


B-1169
terbuthylazine + glyphosate
mefenpyr


B-1170
terbuthylazine + mesotrione
mefenpyr


B-1171
terbuthylazine + nicosulfuron
mefenpyr


B-1172
terbuthylazine + tembotrione
mefenpyr


B-1173
terbuthylazine + topramezone
mefenpyr


B-1174
trifluralin + glyphosate
mefenpyr


B-1175
clodinafop-propargyl
H-12


B-1176
cycloxydim
H-12


B-1177
cyhalofop-butyl
H-12


B-1178
fenoxaprop-P-ethyl
H-12


B-1179
pinoxaden
H-12


B-1180
profoxydim
H-12


B-1181
tepraloxydim
H-12


B-1182
tralkoxydim
H-12


B-1183
esprocarb
H-12


B-1184
prosulfocarb
H-12


B-1185
thiobencarb
H-12


B-1186
triallate
H-12


B-1187
bensulfuron-methyl
H-12


B-1188
bispyribac-sodium
H-12


B-1189
cyclosulfamuron
H-12


B-1190
flumetsulam
H-12


B-1191
flupyrsulfuron-methyl-sodium
H-12


B-1192
foramsulfuron
H-12


B-1193
imazamox
H-12


B-1194
imazapic
H-12


B-1195
imazapyr
H-12


B-1196
imazaquin
H-12


B-1197
imazethapyr
H-12


B-1198
imazosulfuron
H-12


B-1199
iodosulfuron-methyl-sodium
H-12


B-1200
mesosulfuron
H-12


B-1201
nicosulfuron
H-12


B-1202
penoxsulam
H-12


B-1203
propoxycarbazone-sodium
H-12


B-1204
pyrazosulfuron-ethyl
H-12


B-1205
pyroxsulam
H-12


B-1206
rimsulfuron
H-12


B-1207
sulfosulfuron
H-12


B-1208
thiencarbazone-methyl
H-12


B-1209
tritosulfuron
H-12


B-1210
2,4-D and its salts and esters
H-12


B-1211
aminopyralid and its salts and esters
H-12


B-1212
clopyralid and its salts and esters
H-12


B-1213
dicamba and its salts and esters
H-12


B-1214
fluroxypyr-meptyl
H-12


B-1215
quinclorac
H-12


B-1216
quinmerac
H-12


B-1217
B-9
H-12


B-1218
diflufenzopyr
H-12


B-1219
diflufenzopyr-sodium
H-12


B-1220
clomazone
H-12


B-1221
diflufenican
H-12


B-1222
fluorochloridone
H-12


B-1223
isoxaflutol
H-12


B-1224
mesotrione
H-12


B-1225
picolinafen
H-12


B-1226
sulcotrione
H-12


B-1227
tefuryltrione
H-12


B-1228
tembotrione
H-12


B-1229
topramezone
H-12


B-1230
H-7
H-12


B-1231
atrazine
H-12


B-1232
diuron
H-12


B-1233
fluometuron
H-12


B-1234
hexazinone
H-12


B-1235
isoproturon
H-12


B-1236
metribuzin
H-12


B-1237
propanil
H-12


B-1238
terbuthylazine
H-12


B-1239
paraquat dichloride
H-12


B-1240
flumioxazin
H-12


B-1241
oxyfluorfen
H-12


B-1242
saflufenacil
H-12


B-1243
sulfentrazone
H-12


B-1244
H-1
H-12


B-1245
H-2
H-12


B-1246
glyphosate
H-12


B-1247
glyphosate-isopropylammonium
H-12


B-1248
glyphosate-trimesium (sulfosate)
H-12


B-1249
glufosinate
H-12


B-1250
glufosinate-ammonium
H-12


B-1251
pendimethalin
H-12


B-1252
trifluralin
H-12


B-1253
acetochlor
H-12


B-1254
cafenstrole
H-12


B-1255
dimethenamid-P
H-12


B-1256
fentrazamide
H-12


B-1257
flufenacet
H-12


B-1258
mefenacet
H-12


B-1259
metazachlor
H-12


B-1260
metolachlor-S
H-12


B-1261
pyroxasulfone
H-12


B-1262
isoxaben
H-12


B-1263
dymron
H-12


B-1264
indanofan
H-12


B-1265
oxaziclomefone
H-12


B-1266
triaziflam
H-12


B-1267
atrazine + H-1
H-12


B-1268
atrazine + glyphosate
H-12


B-1269
atrazine + mesotrione
H-12


B-1270
atrazine + nicosulfuron
H-12


B-1271
atrazine + tembotrione
H-12


B-1272
atrazine + topramezone
H-12


B-1273
clomazone + glyphosate
H-12


B-1274
diflufenican + clodinafop-propargyl
H-12


B-1275
diflufenican + fenoxaprop-P-ethyl
H-12


B-1276
diflufenican + flupyrsulfuron-methyl-sodium
H-12


B-1277
diflufenican + glyphosate
H-12


B-1278
diflufenican + mesosulfuron-methyl
H-12


B-1279
diflufenican + pinoxaden
H-12


B-1280
diflufenican + pyroxsulam
H-12


B-1281
flumetsulam + glyphosate
H-12


B-1282
flumioxazin + glyphosate
H-12


B-1283
imazapic + glyphosate
H-12


B-1284
imazethapyr + glyphosate
H-12


B-1285
isoxaflutol + H-1
H-12


B-1286
isoxaflutol + glyphosate
H-12


B-1287
metazachlor + H-1
H-12


B-1288
metazachlor + glyphosate
H-12


B-1289
metazachlor + mesotrione
H-12


B-1290
metazachlor + nicosulfuron
H-12


B-1291
metazachlor + terbuthylazine
H-12


B-1292
metazachlor + topramezone
H-12


B-1293
metribuzin + glyphosate
H-12


B-1294
pendimethalin + H-1
H-12


B-1295
pendimethalin + clodinafop-propargyl
H-12


B-1296
pendimethalin + fenoxaprop-P-ethyl
H-12


B-1297
pendimethalin + flupyrsulfuron-methyl-sodium
H-12


B-1298
pendimethalin + glyphosate
H-12


B-1299
pendimethalin + mesosulfuron-methyl
H-12


B-1300
pendimethalin + mesotrione
H-12


B-1301
pendimethalin + nicosulfuron
H-12


B-1302
pendimethalin + pinoxaden
H-12


B-1303
pendimethalin + pyroxsulam
H-12


B-1304
pendimethalin + tembotrione
H-12


B-1305
pendimethalin + topramezone
H-12


B-1306
pyroxasulfone + tembotrione
H-12


B-1307
pyroxasulfone + topramezone
H-12


B-1308
sulfentrazone + glyphosate
H-12


B-1309
terbuthylazine + H-1
H-12


B-1310
terbuthylazine + foramsulfuron
H-12


B-1311
terbuthylazine + glyphosate
H-12


B-1312
terbuthylazine + mesotrione
H-12


B-1313
terbuthylazine + nicosulfuron
H-12


B-1314
terbuthylazine + tembotrione
H-12


B-1315
terbuthylazine + topramezone
H-12


B-1316
trifluralin + glyphosate
H-12


B-1317
2-1
—


B-1318
2-2
—


B-1319
2-3
—


B-1320
2-4
—


B-1321
2-5
—


B-1322
2-6
—


B-1323
2-7
—


B-1324
2-8
—


B-1325
2-9
—


B-1326
2-1
benoxacor


B-1327
2-2
benoxacor


B-1328
2-3
benoxacor


B-1329
2-4
benoxacor


B-1330
2-5
benoxacor


B-1331
2-6
benoxacor


B-1332
2-7
benoxacor


B-1333
2-8
benoxacor


B-1334
2-9
benoxacor


B-1335
2-1
cloquintocet


B-1336
2-2
cloquintocet


B-1337
2-3
cloquintocet


B-1338
2-4
cloquintocet


B-1339
2-5
cloquintocet


B-1340
2-6
cloquintocet


B-1341
2-7
cloquintocet


B-1342
2-8
cloquintocet


B-1343
2-9
cloquintocet


B-1344
2-1
cyprosulfamide


B-1345
2-2
cyprosulfamide


B-1346
2-3
cyprosulfamide


B-1347
2-4
cyprosulfamide


B-1348
2-5
cyprosulfamide


B-1349
2-6
cyprosulfamide


B-1350
2-7
cyprosulfamide


B-1351
2-8
cyprosulfamide


B-1352
2-9
cyprosulfamide


B-1353
2-1
dichlormid


B-1354
2-2
dichlormid


B-1355
2-3
dichlormid


B-1356
2-4
dichlormid


B-1357
2-5
dichlormid


B-1358
2-6
dichlormid


B-1359
2-7
dichlormid


B-1360
2-8
dichlormid


B-1361
2-9
dichlormid


B-1362
2-1
fenchlorazole


B-1363
2-2
fenchlorazole


B-1364
2-3
fenchlorazole


B-1365
2-4
fenchlorazole


B-1366
2-5
fenchlorazole


B-1367
2-6
fenchlorazole


B-1368
2-7
fenchlorazole


B-1369
2-8
fenchlorazole


B-1370
2-9
fenchlorazole


B-1371
2-1
isoxadifen


B-1372
2-2
isoxadifen


B-1373
2-3
isoxadifen


B-1374
2-4
isoxadifen


B-1375
2-5
isoxadifen


B-1376
2-6
isoxadifen


B-1377
2-7
isoxadifen


B-1378
2-8
isoxadifen


B-1379
2-9
isoxadifen


B-1380
2-1
mefenpyr


B-1381
2-2
mefenpyr


B-1382
2-3
mefenpyr


B-1383
2-4
mefenpyr


B-1384
2-5
mefenpyr


B-1385
2-6
mefenpyr


B-1386
2-7
mefenpyr


B-1387
2-8
mefenpyr


B-1388
2-9
mefenpyr


B-1389
2-1
H-11


B-1390
2-2
H-11


B-1391
2-3
H-11


B-1392
2-4
H-11


B-1393
2-5
H-11


B-1394
2-6
H-11


B-1395
2-7
H-11


B-1396
2-8
H-11


B-1397
2-9
H-11


B-1398
2-1
H-12


B-1399
2-2
H-12


B-1400
2-3
H-12


B-1401
2-4
H-12


B-1402
2-5
H-12


B-1403
2-6
H-12


B-1404
2-7
H-12


B-1405
2-8
H-12


B-1406
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 system 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 crop plants.







The following examples will further illustrate the invention:


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 tables that follow, 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: 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 5:95 to 100:0 over 5 minutes at 40° C., flow rate 1.8 mL/min.


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


HPLC column: Luna-C18(2) 5 μm column (Phenomenex), 2.0*50 mm; mobile phase: acetonitrile+0.0625% trifluoroacetic acid (TFA)/water+0.0675% TFA, using a gradient from 10:90 to 80:20 over 4.0 minutes at 40° C., flow rate 0.8 mL/min. MS: quadrupole electrospray ionization, 70 V (positive mode).


DCM: dichloromethane


DIPEA: diisopropylethylamine


DIC (N,N′-diisopropyl carbodiimide


DMAP: Dimethylaminopyridine


DMF: N,N-dimethylformamide


MS: Mass spectrometry


EtOAc: acetic acid ethyl ester


THF: tetrahydrofuran


TFA: trifluoroacetic acid


EXAMPLE 1
Preparation of: 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-N-(1-methyltetrazol-5-yl)benzamide
Step 1: Methyl 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-benzoate



embedded image


To a solution of triphosgene (640 mg, 2.19 mmol) in DCM (8 mL) a solution of commercially available methyl 3-amino-2,5-dichloro-benzoate (800 mg, 3.65 mol) in DCM (8 mL) was added. Then DIPEA (diisopropylethylamine, 844 mg, 6.57 mmol) was added to the mixture at 0° C. under N2 atmosphere. The mixture was stirred at 0° C. for 3 h. N-cyclopropylcyclopropanamine hydrochloride (960 mg, 7.3 mmol) and triethylamine (1.45 g, 14.6 mmol) was added and the mixture was stirred for further 3 h at 15° C. To the reaction mixture 20 mL H2O was added. The layers were separated and andn the aqueous layer was washed with DCM. The combined organic layers were washed with brine and dried over Na2SO4. After concentration in vacuo the compound was purified by column chromatography to give the title compound (1.642 g, crude) as a light yellow solid.



1H NMR (400 MHz, CDCl3), δ 8.74 (d, 1H), 8.22 (s, 1H), 7.43 (d, 1H), 3.96-3.91 (m, 3H), 2.63-2.55 (m, 2H), 1.01-0.95 (m, 4H), 0.92-0.87 (m, 4H)


Step 2: 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-benzoic acid



embedded image


To a solution of methyl 2,5-dichloro-3-(dicyclopropylcarbamoylamino) benzoate (1 g, crude) in THF/H2O (10 mL/2.5 mL) LiOH (420 mg, 17.5 mmol) was added at 0° C. under N2 atmosphere. It was stirred at 15° C. for 2 days. The reaction mixture was adjusted to pH 3 with aqueous 1 N HCl solution and the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give 2,5-dichloro-3-(dicyclopropylcarbamoylamino)benzoic acid as a crude solid which was used without further purification for the next step.



1H NMR (400 MHz, CDCl3), δ 8.50-8.36 (m, 1H), 8.25 (s, 1H), 7.41 (br d, 1H), 2.71-2.57 (m, 2H), 0.87 (br d, J=5.5 Hz, 4H), 0.84-0.76 (m, 4H)


Step 3: pentafluorophenyl 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-benzoate



embedded image


To a solution of 2,5-dichloro-3-(dicyclopropylcarbamoylamino) benzoic acid (1 g, 2.9 mmol), 2,3,4,5,6-pentafluorophenol (810 mg, 4.4 mmol) and DMAP (35 mg, 0.29 mmol) in DMF (10 mL) DIC (554 mg, 4.4 mmol) was added at 0° C. The mixture was stirred at 10° C. for 10 h. The reaction mixture was poured into 20 mL lithium chloride solution (water, 4%), extracted with EtOAc and the organic layers were washed with brine, dried over Na2SO4, concentrated in vacuo and purified by column chromatography to give the title compound (1.1 g, crude) as a white solid.



1H NMR (400 MHz, CDCl3), δ 8.89 (d, 1H), 8.29 (s, 1H), 7.72 (d, 1H), 2.62 (me, 2H), 1.05-0.97 (m, 4H), 0.96-0.89 (m, 4H)


Step 4: 2,5-dichloro-3-(dicyclopropylcarbamoylamino)-N-(1-methyltetrazol-5-yl)benzamide



embedded image


To a solution of 1-methyltetrazol-5-amine (481 mg, 4.86 mmol) in NMP (16 mL) NaH (60%, 162 mg, 4.05 mmol) was added at 0° C. and the mixture was stirred for 0.5 h. Then, 2,3,4,5,6-pentafluorophenyl 2,5-dichloro-3-(dicyclopropylcarbamoylamino) benzoate (800 mg, 1.62 mmol) in NMP (4 mL) was added, and the mixture was stirred at 15° C. for another 8 h. The reaction mixture was poured into lithium chloride solution (4%, 30 mL). The the mixture was adjusted to pH 6-7 with 1 N HCl, extracted with EtOAc, the combined organic layers were washed with brine, dried over Na2SO4, concentrated in vacuo and purified by chromatography to give the title compound (220 mg) as a white solid.



1H NMR (400 MHz, d6-DMSO), δ 8.34 (d, 1H), 8.22 (s, 1H), 7.42 (d, 1H), 3.91 (s, 3H), 2.66-2.60 (m, 2H), 0.92-0.85 (m, 4H), 0.81 (q, 4H).


EXAMPLE 2
Preparation of: 2,5-dichloro-3-[(2,2,2-trifluoroethyl)(methyl)carbamoylamino]-N-(1-methyltetrazol-5-yl)benzamide



embedded image


The title compound was prepared by analogy to the method described in Example 1.


HPLC-MS: m/z 425.8 (M+H)+


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 containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this 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 250 g/ha the following compounds were tested in post-emergence tests against:


ECHCG (Echinocloa crus-galli)


AMARE (Amaranthus retroflexus)


CHEAL (Chenopodium album)


















Example
ECHCG
AMARE
CHEAL









1
>80
>80
>80



2
>80
>80
>80









Claims
  • 1. A compound of formula I,
  • 2. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Q is Q1.
  • 3. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Q is Q2.
  • 4. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Q is Q3.
  • 5. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Q is Q4.
  • 6. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R1 is selected from the group consisting of halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkoxy-Z1, R1b—S(O)k—Z1.
  • 7. The compound as claimed in claim 6, or an agriculturally suitable salt thereof, where R1 is selected from the group consisting of halogen and C1-C4-alkyl.
  • 8. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R2 is R2cR2dNC(O)NR2n—Z2, where R2n is selected from the group consisting of hydrogen and C1-C6-alkyl.
  • 9. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Z2 in R2 is a covalent bond and R2c and R2d independently of each other are selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C6-haloalkyl, 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, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.
  • 10. The compound as claimed in claim 8, or an agriculturally suitable salt thereof, where Z2 in R2 is a covalent bond R2c is selected from the group consisting of C1-C4-alkyl, C3-C7-cycloalkyl and C1-C4-haloalkyl and R2d is selected from the group consisting of C1-C6-alkyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C2-alkyl and C1-C6-haloalkyl.
  • 11. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where Z2 in R2 is a covalent bond and R2c and R2d 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 ═O, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy.
  • 12. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R3 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy, and R2b—S(O)k.
  • 13. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R3 is selected from the group consisting of hydrogen, halogen and C1-C2-haloalkyl.
  • 14. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R4 is selected from the group consisting cyano, halogen, nitro, C1-C2-alkyl, and C1-C2-haloalkyl.
  • 15. The compound as claimed in claim 14, or an agriculturally suitable salt thereof, where R4 is selected from the group consisting of fluorine and chlorine.
  • 16. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, where R6 is selected from the group consisting of C1-C6-alkyl, C1-C4-alkoxy-C1-C4-alkyl, and phenyl.
  • 17. The compound as claimed in claim 1, or an agriculturally suitable salt thereof, which is selected from the compounds of the following formulae I.A.I and I.D.I,
  • 18. The compound as claimed in claim 17, or an agriculturally suitable salt thereof, where, R1, R2c, R2d, R3 and R4 are as defined in the following tables:
  • 19. A composition comprising the compound as claimed in claim 1, or an agriculturally suitable salt thereof, and at least one auxiliary for formulating crop protection compounds.
  • 20. A method for controlling unwanted vegetation comprising applying the compound as claimed in claim 1, or an agriculturally suitable salt thereof, or of the composition thereof to plants, their seed and/or their habitat.
  • 21. A method for controlling unwanted vegetation comprising allowing a herbicidally effective amount of the compound as claimed in claim 1, or an agriculturally suitable salt thereof, or of the composition thereof to act on plants, their seed and/or their habitat.
Priority Claims (1)
Number Date Country Kind
17173421.3 May 2017 EP regional
PCT Information
Filing Document Filing Date Country Kind
PCT/EP2018/064047 5/29/2018 WO 00