Herbicidal malonamides

Abstract

The present application relates to malonamide compounds of formula (I), wherein the variables are defined in the claims and description, and to compositions comprising these compounds. The present application also relates to the use of said malonamide compounds or corresponding compositions for controlling undesirable plants. Furthermore, the present application relates to methods for controlling undesirable plants, wherein said malonamide compounds or corresponding compositions are applied.

Description

[0001] This invention relates to malondiamide compounds and compositions comprising them. The invention also relates to the use of malondiamide compounds or corresponding compositions in controlling unwanted plants. Furthermore, the invention relates to methods of applying malondiamide compounds or corresponding compositions.

[0002] To control unwanted plants, especially in crops, there is a continuous need for novel herbicides that are highly active and selective and do not have significant toxicity to humans and animals.

[0003] WO 2012 / 130798, WO 2014 / 04882, WO 2014 / 048882, WO 2018 / 228985, WO 2018 / 228986, WO 2019 / 034602, WO 2019 / 145245, WO 2020 / 114932, WO 2020 / 114934 and WO2020 / 182723 describe 3-phenylisooxazoline-5-carboxamides and their use as herbicides.

[0004] WO 87 / 05898 describes the use of malonic acid derivatives for delaying plant growth.

[0005] US3,072,473 describes malonic acid derivatives as plant growth regulators.

[0006] WO 01 / 12183 describes the use of malonic acid derivatives characterized by monocyclic saturated heterocycles having up to two heteroatoms in the treatment of cell adhesion-mediated conditions.

[0007] Existing herbicidal compounds are often insufficient and / or unsatisfactory in their herbicidal activity, especially at low application rates, resulting in poor compatibility with crops.

[0008] Therefore, the object of this invention is to provide other malonamide compounds that possess strong herbicidal activity, sufficiently low toxicity to humans and animals, and / or high compatibility with crops, especially even at low application rates. The malonamide compounds should also exhibit a broad activity spectrum across a wide range of undesirable plants.

[0009] These and other purposes are achieved by compounds of formula (I) as defined below, including their agriculturally usable salts.

[0010] Therefore, the present invention provides a compound of formula (I):

[0011]

[0012] The substituents have the following meanings:

[0013] R 1It can be hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0014] R 2 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0015] R 3 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0016] R 4 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl or C2-C3 haloalkynyl;

[0017] R 5 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0018] R 6 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0019] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. dNCOR d and NC(O)OR d The unit, wherein one carbon atom has p oxo groups, and wherein the ring is bounded by n R groups. g replace;

[0020] R 9 It can be hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C3 alkoxy-C1-C3 alkoxy;

[0021] X is the key (X 0 () or selected from the following divalent units: (X) 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ):

[0022]

[0023] R 10 -R 15 Each of the following elements appears independently and independently: hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyanide, and CO2R. e CONR b R d R a Or C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, wherein each of the last four aliphatic and alicyclic groups is replaced by m groups selected from the following: fluorine, chlorine, bromine, iodine, hydroxyl and cyano; or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, wherein each of the last four groups has an aliphatic and alicyclic structural portion replaced by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and C1-C2 alkoxy;

[0024] Y represents hydrogen, cyano, hydroxyl, or Z.

[0025] Or C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 The alkynyl group, wherein each of the four aliphatic and alicyclic groups mentioned later is replaced by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n Ra SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e ;

[0026] Z is 3, 4, 5, 6, 7, or 8-membered saturated, partially unsaturated, fully unsaturated, or aromatic monocyclic, bicyclic (including fused, bridged, and spirocyclic) or polycyclic, excluding phenyl, formed of r carbon atoms, k nitrogen atoms, n sulfur atoms, and n oxygen atoms, and substituted by m groups selected from the following: CO2R e CONR b R h S(O) n R a SO2NR b R d SO2NR b COR e COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2Re NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e R b R c R e and R f Furthermore, the sulfur and carbide ring atoms in this structure have n oxo groups;

[0027] R a Each is independently a C1-C6 alkyl, C2-C4 alkynyl or C3-C6 cycloalkyl group, each of which is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, iodine, cyano, hydroxyl and C1-C3 alkoxy.

[0028] R b Each independently is either hydrogen or R a ;

[0029] R c Each can be independently classified as fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, or S(O). n R a Or C1-C6 alkoxy, C3-C6 alkenoxy, or C3-C6 alkynoxy, wherein the aliphatic portion of each of the three groups mentioned later is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, and C1-C2 alkoxy.

[0030] R d Each of the six groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, COOR a The following groups are included: C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfinyl, phenylsulfonyl, and phenylthio; wherein the aliphatic or aromatic structural portion of the latter seven groups may be substituted by m groups selected from fluorine, chlorine, and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2, or 3 heteroatoms selected from N, O, and S as ring members;

[0031] R eEach of the six groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, COOR a The following groups are included: C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfinyl, phenylsulfonyl, and phenylthio; wherein the aliphatic or aromatic structural portion of the latter seven groups may be substituted by m groups selected from fluorine, chlorine, and bromine; and a 5- or 6-membered heteroaromatic ring containing 1, 2, or 3 heteroatoms selected from N, O, and S as ring members;

[0032] R f Each is independently a C1-C3 alkyl or C1-C3 alkoxy;

[0033] R g Each of the following can be independently a halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, or C1-C3 alkylsulfonyl; or two Rs bonded to the same carbon atom. g Together they form a methylene group (=CH2);

[0034] R h Each of the six groups is independently hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0035] k can be 0, 1, 2, 3 or 4;

[0036] m can be 0, 1, 2, 3, 4 or 5 independently;

[0037] n can be 0, 1, or 2 independently;

[0038] p is 0 or 1;

[0039] q can be 1, 2, 3, 4, 5, or 6;

[0040] r is 1, 2, 3, 4, 5, 6, 7 or 8;

[0041] u is 0, 1, or 2;

[0042] v can be 0, 1, 2, or 3;

[0043] w is 0, 1, or 2;

[0044] x is 0, 1, or 2;

[0045] The condition is that at least one of u, v, w, and x is not 0;

[0046] This includes its agricultural salts, stereoisomers, and tautomers.

[0047] In a specific implementation, in compound (I)

[0048] R d Each of the six groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, COOR a C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfinyl, phenylsulfonyl, phenylthio; and 5- or 6-membered heteroaromatic rings containing 1, 2, or 3 heteroatoms selected from N, O, and S as ring members; and

[0049] R e Each of the six groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, COOR a C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfinyl, phenylsulfonyl, phenylthio; and 5- or 6-membered heteroaromatic rings containing 1, 2 or 3 heteroatoms selected from N, O and S as ring members.

[0050] The present invention also provides formulations comprising at least one compound of formula (I) and an adjuvant commonly used in formulating protective mixtures.

[0051] The present invention also provides a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C).

[0052] The present invention also provides the use of the compound of formula (I) as a herbicide, i.e., for controlling unwanted plants.

[0053] Furthermore, the present invention provides a method for controlling unwanted plants, wherein an effective amount of at least one compound of formula (I) is applied to the plant, its seeds, and / or its growing area.

[0054] If the compound of formula (I) described herein, herbicide compound B, and / or safer agent C can form geometric isomers, such as E / Z isomers, then pure isomers and mixtures thereof can be used according to the present invention.

[0055] If the compound of formula (I) described herein, herbicide compound B, and / or safener C have one or more chiral centers and are therefore present as enantiomers or diastereomers, then both pure enantiomers and diastereomers and mixtures thereof may be used according to the present invention. For example only, the stereoisomeric center in compound (I) is located at X... 1 -X 6 Contains R 10 and R 11 The C atom, of course, under the condition that R 10 and R 11 Different. Another example of a stereoheterogeneous center is one with R. 7 and R 8 The C atoms, provided that the rings formed by these groups and the carbon atoms they are bonded to do not have a rotating mirror axis.

[0056] If the compounds of formula (I) described herein, herbicidal compound B, and / or safener C have ionizable functional groups, they can also be used in their agronomical salt form. Suitable salts are typically salts of cations whose cations and anions do not adversely affect the activity of the active compound, and acid addition salts of acids. For example, the ionizable functional group is -CO2R. e , where R e It is hydrogen. Compound (I) containing this -C(O)OH group can be used in the form of its salt, i.e., in the form containing one or more -C(O)O groups. - M + Used in the form of compounds, where M + It is a cationic equivalent. Examples of agriculturally usable cationic compounds are given below.

[0057] Preferred cations are alkali metal ions, preferably lithium, sodium, and potassium ions; alkaline earth metal ions, preferably calcium and magnesium ions; and transition metal ions, preferably manganese, copper, zinc, and iron ions. Additionally, ammonium and substituted ammonium compounds in which 1-4 hydrogen atoms are replaced by C1-C4 alkyl, hydroxy-C1-C4 alkyl, C1-C4 alkoxy-C1-C4 alkyl, hydroxy-C1-C4 alkoxy-C1-C4 alkyl, phenyl, or benzyl groups are preferred, including ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, and diisopropylammonium. Ammonium, trimethylammonium, triethylammonium, triisopropylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (alcoholamine salt), 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diethylene glycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diethanolamine salt), tri(2-hydroxyethyl)ammonium (triethanolamine salt), tri(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), and others. The ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, such as trimethylsulfonium, and sulfonium oxide ions, preferably tri(C1-C4 alkyl)sulfonium oxide, and finally, salts of polyamines such as N,N-di(3-aminopropyl)methylamine and diethylenetriamine.

[0058] The main anions of useful acid addition salts are chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4 alkanic acids, with formate, acetate, propionate, and butyrate being preferred.

[0059] Compound (I) can exist in different tautomer forms. For example, if ring Z is a lactam, i.e., containing an amide group as a ring member (i.e., an unsubstituted secondary nitrogen ring atom adjacent to a carbocyclic atom with an oxo group), then the ring moiety -N(H)-C(=O)- can be in equilibrium with its tautomer form -N=C(OH)-. The same applies to the two forced-existence amide groups -N(R) in the malondiamide moiety. 1 )-C(=O)-C(R 7 (R) 8 )-C(=O)-N(R 9 -, if R 1 and R 9 One or two of them are hydrogen:

[0060] If only R 1 If the hydrogen content is 0, then the malondiamide structural moiety can be -N(H)-C(=O)-C(R) 7 (R) 8 )-C(=O)-N(R9 - or as -N=C(OH)-C(R) 7 (R) 8 )-C(=O)-N(R 9 - or a mixture of the two forms exists;

[0061] If only R 9 If the hydrogen content is 0, then the malondiamide structural moiety can act as -N(R) 1 )-C(=O)-C(R 7 (R) 8 -C(=O)-N(H)- or as -N(R) 1 )-C(=O)-C(R 7 (R) 8 It exists in the form of )-C(OH)=N- or a mixture of both;

[0062] If R 1 and R 9 Since both are hydrogen atoms, the malondiamide structural moiety can be represented as -N(H)-C(=O)-C(R) 7 (R) 8 -C(=O)-N(H)- or as -N=C(OH)-C(R) 7 (R) 8 -C(=O)-N(H)- or as -N(H)-C(=O)-C(R) 7 (R) 8 -C(OH)=N- or as -N=C(OH)-C(R) 7 (R) 8 It exists in the form of )-C(OH)=N- or a mixture of two, three, or all four.

[0063] The amount of one or more tautomers present depends on the complete molecular structure, and even more so on the surrounding conditions (the presence or absence of solvent, solvent type, pH, temperature, etc.).

[0064] The carboxyl-containing compounds of formula (I), herbicidal compound B, and / or safener C described herein may be in the form of an acid, in the form of an agriculturally usable salt as described above, or in the form of an agriculturally usable derivative, for example as an amide, such as mono- and di-C1-C6 alkylamides or arylamides, or as an ester, such as an allyl ester, propargyl ester, or C1-C6 alkyl ester. 10 Alkyl esters, alkoxyalkyl esters, tetrahydrofuranylmethyl ((tetrahydrofuran-2-yl)methyl) esters, and also as thioesters, for example as C1-C 10Alkyl thioesters are used. Preferred mono- and di-C1-C6 alkylamides are methyl and dimethylamides. Preferred arylamides are, for example, benzoylamide and 2-chlorobenzoylamide. Preferred alkyl esters are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, methylhexyl (1-methylhexyl), methylheptyl (1-methylheptyl), heptyl, octyl, or isooctyl (2-ethylhexyl) esters. Preferred C1-C4 alkoxy-C1-C4 alkyl esters are straight-chain or branched C1-C4 alkoxyethyl esters, such as 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butoxyethyl), 2-butoxypropyl, or 3-butoxypropyl esters. Straight-chain or branched C1-C 10 An example of an alkylthioester is an ethylthioester.

[0065] The term “undesirable plant” (“weed”) should be understood to include any plant growing in non-crop areas or crop sites or sites for sowing and other desired crops, wherein the plant is any plant variety other than the sown or desired crop (if any), including its germinating seeds, seedlings, and formed plants. In the broadest sense, a weed is a plant considered undesirable in a particular location.

[0066] The terms used in the definition of organic groups in the variables, such as the expression "halogen", are collective terms representing the members of these groups of organic units.

[0067] prefix C x -C y This indicates the possible number of carbon atoms under a specific condition. All hydrocarbon chains can be straight or branched.

[0068] Halogens: fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine.

[0069] Alkyl groups and complex groups such as alkoxy, alkylamino, alkylthio, and alkoxycarbonyl have 1-12 carbon atoms (=C1-C2). 12 Alkyl group or 1-10 carbon atoms (C1-C2) 10Alkyl groups, typically with 1-6 carbon atoms (=C1-C6 alkyl), particularly 1-4 carbon atoms (=C1-C4 alkyl), especially 1-3 carbon atoms (=C1-C3 alkyl) or 1 or 2 carbon atoms (=C1-C2 alkyl), are saturated straight-chain or branched hydrocarbon groups. C1-C2 alkyl groups are methyl or ethyl. C1-C3 alkyl groups are methyl, ethyl, n-propyl, or isopropyl. Examples of C1-C4 alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl (=sec-butyl), isobutyl, and tert-butyl. In addition to those mentioned for C1-C4 alkyl groups, examples of C1-C6 alkyl groups are 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. In addition to those mentioned for C1-C6 alkyl groups, examples of C1-C8 alkyl groups include n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl, and 2-propylpentyl. In addition to those mentioned for C1-C8 alkyl groups, C1-C... 12 Examples of alkyl groups are nonyl, decyl, 2-propylheptyl, 3-propylheptyl, undecyl, dodecyl and their positional isomers.

[0070] Haloalkyl: having 1-10 carbon atoms (=C1-C2) 10The alkyl group is a straight-chain or branched alkyl group (as described above) typically with 1-6 carbon atoms (=C1-C6 haloalkyl), more typically with 1-3 carbon atoms (=C1-C3 haloalkyl), wherein some or all of the hydrogen atoms in these groups are replaced by the aforementioned halogen atoms. In one embodiment, the alkyl group is substituted at least once or completely with a specific halogen atom, preferably fluorine, chlorine, or bromine. In another embodiment, the alkyl group is partially or completely halogenated with different halogen atoms; in the case of mixed halogen substitution, a combination of chlorine and fluorine is preferred. C1-C3 haloalkyl groups are particularly preferred, and C1-C2 haloalkyl groups are more preferred, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichloromonofluoromethyl, monochlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, or pentafluoroethyl. Examples of C1-C3 haloalkyl groups, other than those mentioned for C1-C2 haloalkyl groups, are 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoropropyl-2-yl, and 3-chloropropyl.

[0071] Hydroxyalkyl refers to a straight-chain or branched alkyl group as defined above, typically having 1-6 carbon atoms (=C1-C6 hydroxyalkyl), more often 1-3 carbon atoms (=C1-C3 hydroxyalkyl), wherein one hydrogen atom of the group is replaced by a hydroxyl group. Examples are hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-2-propyl, 2-hydroxy-2-propyl, etc.

[0072] Alkenyl groups and complex groups such as alkenyloxy groups: have 2-12 carbon atoms (=C2-C) 12 Alkenyl group or 2-10 carbon atoms (=C2-C) 10Alkenyl groups, for example, 2-8 carbon atoms (=C2-C8 alkenyl groups) or 2-6 carbon atoms (=C2-C6 alkenyl groups), particularly 2-4 carbon atoms (=C2-C4 alkenyl groups) or 2 or 3 carbon atoms (=C2-C3 alkenyl groups); and unsaturated straight-chain or branched hydrocarbon groups with a double bond at any position. According to the invention, smaller alkenyl groups, such as C2-C4 or C2-C3 alkenyl groups, may be preferred; on the other hand, larger alkenyl groups, such as C5-C8 alkenyl groups, may also be preferred.Examples of C2-C3 alkenyl groups are vinyl, 1-propenyl, 2-propenyl, and 1-methylvinyl; examples of C2-C4 alkenyl groups, in addition to those mentioned for C2-C3 alkenyl groups, are 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, and 2-methyl-2-propenyl; examples of C2-C6 alkenyl groups, in addition to those mentioned for C2-C4 alkenyl groups, are 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 alkenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; except for those mentioned for C2-C6 alkenyl groups, C2-C. 12Examples of alkenyl groups are 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, nonenyl, decenyl, undecenyl, dodecenyl, and their positional isomers. Examples of C3-C6 alkenyl groups are those mentioned above for C2-C6 alkenyl groups, excluding vinyl groups.

[0073] Halogenated alkenyl groups: alkenyl groups as described above that are partially or completely substituted with fluorine, chlorine, bromine and / or iodine, such as 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1-yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl or 2,3-dibromobut-2-en-1-yl.

[0074] The alkynyl group and complex groups such as the alkynyl group in the alkynoxy group have 2-12 carbon atoms (=C2-C). 12 (alkynyl group) or 2-10 carbon atoms (=C2-C) 10The alkynyl group, for example, has 2-8 carbon atoms (=C2-C8 alkynyl) or 2-6 carbon atoms (=C2-C6 alkynyl), especially 2-4 carbon atoms (=C2-C4 alkynyl) or 2 or 3 carbon atoms (=C2-C3 alkynyl); and is a straight-chain or branched hydrocarbon group with one or two triple bonds at any position. Examples of C2-C3 alkynyl groups are ethynyl, 1-propynyl, and 2-propynyl. Examples of C2-C4 alkynyl groups, in addition to those mentioned for C2-C3 alkynyl groups, are 1-butynyl, 2-butynyl, 3-butynyl, and 1-methyl-2-propynyl. In addition to those mentioned for C2-C3 ynyl groups, examples of C2-C6 ynyl groups include 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, and 1-methyl-4-pentynyl. 2-Methyl-3-pentynyl, 2-Methyl-4-pentynyl, 3-Methyl-1-pentynyl, 3-Methyl-4-pentynyl, 4-Methyl-1-pentynyl, 4-Methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl.

[0075] Halogenated alkynyl group: alkynyl groups as described above that are partially or completely substituted with fluorine, chlorine, bromine and / or iodine, such as 1,1-difluoroprop-2-yn-1-yl, 3-chloroprop-2-yn-1-yl, 3-bromoprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohexyl-4-yn-1-yl, or 6-iodohexyl-5-yn-1-yl.

[0076] Cycloalkyl groups and cycloalkyl structural moieties in complex groups: have 3-10 carbon atoms (=C3-C4). 10A monocyclic or bicyclic saturated hydrocarbon group having cycloalkyl or 3-8 carbon atoms (=C3-C8 cycloalkyl), particularly 3-6 carbon atoms (=C3-C6 cycloalkyl), 3-5 carbon atoms (=C3-C5 cycloalkyl), or 3-4 carbon atoms (=C3-C4 cycloalkyl) as a ring member (only). Examples of monocyclic saturated alicyclic groups having 3 or 4 carbon atoms are cyclopropyl and cyclobutyl. Examples of monocyclic saturated alicyclic groups having 3-5 carbon atoms are cyclopropyl, cyclobutyl, and cyclopentyl. Examples of monocyclic saturated alicyclic groups having 3-6 carbon atoms are cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of monocyclic saturated alicyclic groups having 3-8 carbon atoms are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl. Examples of bicyclic groups include bicyclic [1.1.1]pentyl, bicyclic [2.1.1]hexyl, bicyclic [2.2.1]heptyl, bicyclic [2.2.2]octyl and bicyclic [3.2.1]octyl.

[0077] The halogenated cycloalkyl group in halocycloalkyl groups, halocycloalkoxy groups, and halocycloalkyl carbonyl groups has 3-10 carbon ring members (C3-C4). 10 The saturated hydrocarbon group (as described above) of a halogenated cycloalkyl group or a 3-8 carbocyclic member (C3-C8 halogenated cycloalkyl group), preferably a 3-5 carbocyclic member (C3-C5 halogenated cycloalkyl group) or a 3 or 4 carbocyclic member (C3-C4 halogenated cycloalkyl group), wherein some or all of the hydrogen atoms can be replaced by the halogen atoms described above, especially fluorine, chlorine and bromine. Examples include 1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 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, etc.

[0078] Hydroxycycloalkyl: A monocyclic or bicyclic alicyclic group typically having 3-6 carbon atoms (“C3-C6 hydroxycycloalkyl”), preferably 3-5 carbon atoms (“C3-C5 hydroxycycloalkyl”), wherein at least one, for example 1, 2, 3, 4 or 5 hydrogen atoms are substituted with a hydroxyl group. Examples are 1-hydroxycyclopropyl, 2-hydroxycyclopropyl, 1,2-dihydroxycyclopropyl, 2,3-dihydroxycyclopropyl, 1-hydroxycyclobutyl, 2-hydroxycyclobutyl, 3-hydroxycyclobutyl, 1,2-dihydroxycyclobutyl, 1,3-dihydroxycyclobutyl, 2,3-dihydroxycyclobutyl, 1-hydroxycyclopentyl, 2-hydroxycyclopentyl, 3-hydroxycyclopentyl, 1,2-dihydroxycyclopentyl, 1,3-dihydroxycyclopentyl, 2,3-dihydroxycyclopentyl, etc.

[0079] Cycloalkylalkyl: An alkyl group as defined above, wherein one hydrogen atom is substituted by a cycloalkyl group as defined above. The term “C3-C6 cycloalkyl-C1-C3 alkyl” as used herein refers to an alkyl group having 1-3 carbon atoms as defined above, wherein one hydrogen atom is substituted by a C3-C6 cycloalkyl group as defined above. Examples include cyclopropylmethyl, cyclopropyl-1-ethyl, cyclopropyl-2-ethyl, cyclopropyl-1-propyl, cyclopropyl-2-propyl, cyclopropyl-3-propyl, cyclobutylmethyl, cyclobutyl-1-ethyl, cyclobutyl-2-ethyl, cyclobutyl-1-propyl, cyclobutyl-2-propyl, cyclobutyl-3-propyl, cyclopentylmethyl, cyclopentyl-1-ethyl, cyclopentyl-2-ethyl, cyclopentyl-1-propyl, cyclopentyl-2-propyl, cyclopentyl-3-propyl, cyclohexylmethyl, cyclohexyl-1-ethyl, cyclohexyl-2-ethyl, cyclohexyl-1-propyl, cyclohexyl-2-propyl, cyclohexyl-3-propyl, etc.

[0080] Alkoxy groups and alkoxy structural moieties in complex groups, such as alkoxyalkyl groups: alkyl groups as defined above, connected to the rest of the molecule via oxygen atoms, typically having 1-10 carbon atoms (C1-C2). 10Alkoxy groups, preferably with 1-6 carbon atoms (C1-C6 alkoxy), 1-4 carbon atoms (C1-C4 alkoxy), 1-3 carbon atoms (C1-C3 alkoxy), or 1-2 carbon atoms (C1-C2 alkoxy). Examples of C1-C2 alkoxy groups are methoxy and ethoxy; examples of C1-C3 alkoxy groups, other than those mentioned for C1-C2 alkoxy groups, are n-propoxy and 1-methylethoxy (isopropoxy); examples of C1-C4 alkoxy groups, other than those mentioned for C1-C3 alkoxy groups, are butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy; examples of C1-C6 alkoxy groups, other than those mentioned for C1-C4 alkoxy groups, are pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, and 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;

[0081] Haloalkoxy groups: Alkoxy groups as defined above, wherein some or all of the hydrogen atoms in these groups are replaced by the halogen atom, especially fluorine, chlorine, or bromine, as described above under the haloalkyl group. Examples are 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, OC2F5, 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; and also 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecylfluoropentoxy, 6-fluorohexyloxy, 6-chlorohexyloxy, 6-bromohexyloxy, 6-iodohexyloxy or dodecafluorohexyloxy.

[0082] Alkenyl group: An alkenyl group as defined above, attached to the rest of the molecule via an oxygen atom. C2-C6 alkenyl group: A C2-C6 alkenyl group as defined above, attached to the rest of the molecule via an oxygen atom. C3-C6 alkenyl group: A C3-C6 alkenyl group as defined above, attached to the rest of the molecule via an oxygen atom.

[0083] Haloalkenyl group: A haloalkenyl group as defined above, attached to the rest of the molecule via an oxygen atom. C2-C6 haloalkenyl group: A C2-C6 haloalkenyl group as defined above, attached to the rest of the molecule via an oxygen atom. C3-C6 haloalkenyl group: A C3-C6 haloalkenyl group as defined above, attached to the rest of the molecule via an oxygen atom.

[0084] Alkyne group: An alkynyl group as defined above, attached to the rest of the molecule via an oxygen atom. C2-C6 alkynyl group: A C2-C6 alkynyl group as defined above, attached to the rest of the molecule via an oxygen atom. C3-C6 alkynyl group: A C3-C6 alkynyl group as defined above, attached to the rest of the molecule via an oxygen atom.

[0085] Haloalkynyl group: A haloalkynyl group as defined above, attached to the rest of the molecule via an oxygen atom. C2-C6 haloalkynyl group: A C2-C6 haloalkynyl group as defined above, attached to the rest of the molecule via an oxygen atom. C3-C6 haloalkynyl group: A C3-C6 haloalkynyl group as defined above, attached to the rest of the molecule via an oxygen atom.

[0086] Cycloalkoxy: A cycloalkyl group as defined above, attached to the rest of the molecule via an oxygen atom. C3-C6 cycloalkoxy is a C3-C6 cycloalkyl group as defined above, attached to the rest of the molecule via an oxygen atom. Examples of C3-C6 cycloalkoxy groups include cyclopropoxy, cyclobutoxy, cyclopentoxy, and cyclohexoxy.

[0087] Alkoxyalkyl: An alkyl group as defined above, wherein one hydrogen atom is substituted by another alkoxy group as defined above. The term “C1-C3alkoxy-C1-C3 alkyl” as used herein refers to an alkyl group having 1-3 carbon atoms as defined above, wherein one hydrogen atom is substituted by a C1-C3 alkoxy group as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, 1-methoxyethyl, 1-ethoxyethyl, 1-propoxyethyl, 1-isopropoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 1-methoxypropyl, 1-ethoxypropyl, 1-propoxypropyl, 1-isopropoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3-propoxypropyl, 3-isopropoxypropyl, etc.

[0088] Alkoxy: An alkoxy group as defined above, in which one hydrogen atom is replaced by another alkoxy group as defined above. The term "C1-C3 alkoxy" as used herein refers to an alkoxy group as defined above, having 1-3 carbon atoms, in which one hydrogen atom is replaced by a C1-C3 alkoxy group as defined above. Examples include methoxymethoxy, ethoxymethoxy, propoxymethoxy, isopropoxymethoxy, 1-methoxyethoxy, 1-ethoxyethoxy, 1-propoxyethoxy, 1-isopropoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-propoxyethoxy, 2-isopropoxyethoxy, 1-methoxypropoxy, 1-ethoxypropoxy, 1-propoxypropoxy, 1-isopropoxypropoxy, 2-methoxypropoxy, 2-ethoxypropoxy, 2-propoxypropoxy, 2-isopropoxypropoxy, 3-methoxypropoxy, 3-ethoxypropoxy, 3-propoxypropoxy, 3-isopropoxypropoxy, etc.

[0089] Alkyl thioyl group: An alkyl group as defined above, attached to the remainder of the molecule via a sulfur atom, preferably having 1-6, more preferably 1-3, for example, 1 or 2 carbon atoms. C1-C2 alkyl thioyl groups are methylthioyl or ethylthioyl. C1-C3 alkyl thioyl groups are, for example, n-propylthioyl or 1-methylethylthioyl (isopropylthioyl). C1-C6 alkyl thioyl groups also include, for example, butylthioyl, 1-methylpropylthioyl (sec-butylthioyl), 2-methylpropylthioyl (isobutylthioyl), 1,1-dimethylethylthioyl (tert-butylthioyl), pentylthioyl, 1-methylbutylthioyl, 2-methylbutylthioyl, 3-methylbutylthioyl, 1,1-dimethylpropylthioyl, 1,2-dimethylpropylthioyl, 2,2-dimethylpropylthioyl, 1-ethylpropylthioyl, hexylthioyl, 1-methylpentylthioyl, 2-methylpentylthioyl 3-Methylpentylthio, 4-Methylpentylthio, 1,1-dimethylbutyrothio, 1,2-dimethylbutyrothio, 1,3-dimethylbutyrothio, 2,2-dimethylbutyrothio, 2,3-dimethylbutyrothio, 3,3-dimethylbutyrothio, 1-ethylbutyrothio, 2-ethylbutyrothio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, or 1-ethyl-2-methylpropylthio.

[0090] Alkyl sulfinyl group: An alkyl group as defined above, attached to the remainder of the molecule via an S(O) group, preferably having 1-6, more preferably 1-3, for example 1 or 2 carbon atoms. C1-C2 alkyl sulfinyl groups are methyl sulfinyl or ethyl sulfinyl. C1-C3 alkyl sulfinyl groups are, for example, n-propyl sulfinyl or 1-methyl ethyl sulfinyl (isopropyl sulfinyl). C1-C6 alkyl sulfinyl groups, for example, include butyl sulfinyl, 1-methylpropyl sulfinyl (sec-butyl sulfinyl), 2-methylpropyl sulfinyl (isobutyl sulfinyl), 1,1-dimethylethyl sulfinyl (tert-butyl sulfinyl), pentyl sulfinyl, 1-methylbutyl sulfinyl, 2-methylbutyl sulfinyl, 3-methylbutyl sulfinyl, 1,1-dimethylpropyl sulfinyl, 1,2-dimethylpropyl sulfinyl, 2,2-dimethylpropyl sulfinyl, 1-ethylpropyl sulfinyl, hexyl sulfinyl, 1-methylpentyl sulfinyl, 2-methyl... 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.

[0091] Alkyl sulfonyl group: An alkyl group as defined above, attached to the remainder of the molecule via an S(O)2 group, preferably having 1-6, more preferably 1-3, for example 1 or 2 carbon atoms. C1-C2 alkyl sulfonyl groups are methyl sulfonyl or ethyl sulfonyl. C1-C3 alkyl sulfonyl groups are, for example, n-propyl sulfonyl or 1-methyl ethyl sulfonyl (isopropyl sulfonyl). C1-C6 alkylsulfonyl groups also include, for example, butylsulfonyl, 1-methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl), 1,1-dimethylethylsulfonyl (tert-butylsulfonyl), pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl 1,1-dimethylbutylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 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.

[0092] The substituent "oxo" is formed by replacing the CH2 group with a C (=O) group.

[0093] The suffix "-carbonyl" in a group indicates that the group is bonded to the rest of the molecule via a carbonyl C=O group. This is the case, for example, in alkyl carbonyl, haloalkyl carbonyl, amino carbonyl, alkylamino carbonyl, dialkylamino carbonyl, alkoxycarbonyl, and haloalkoxycarbonyl groups.

[0094] Alkoxycarbonyl: An alkoxy group as defined above, attached to the remainder of the molecule via a carbonyl [C(=O)] group. C1-C3 alkoxycarbonyl is a C1-C3 alkoxy group as defined above, attached to the remainder of the molecule via a carbonyl [C(=O)] group. Examples of C1-C3 alkoxycarbonyl are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, and isopropoxycarbonyl. C1-C6 alkoxycarbonyl is a C1-C6 alkoxy group as defined above, attached to the remainder of the molecule via a carbonyl [C(=O)] group. Examples of C1-C6 alkoxycarbonyl, other than those listed for C1-C3 alkoxycarbonyl, are n-butoxycarbonyl, sec-butoxycarbonyl, isobutoxycarbonyl, tert-butoxycarbonyl, pentoxycarbonyl, and hexoxycarbonyl.

[0095] Alkoxycarbonylalkyl: An alkyl group as defined above, wherein one hydrogen atom is replaced by an alkoxycarbonyl group as defined above. C1-C6 alkoxycarbonyl-C1-C6 alkyl: A C1-C6 alkyl group as defined above, wherein one hydrogen atom is replaced by a C1-C6 alkoxycarbonyl group as defined above.

[0096] Phenyl-C1-C3 alkyl is a C1-C3 alkyl group as defined above, wherein one hydrogen atom is substituted by a phenyl ring. Examples are benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, or 2-phenyl-2-propyl.

[0097] The phenylthio group is a phenyl ring connected to the rest of the molecule via an S atom.

[0098] The benzenesulfinyl group is a phenyl ring connected to the rest of the molecule via an S(O) group.

[0099] The benzenesulfonyl group is a phenyl ring connected to the rest of the molecule via an S(O)2 group.

[0100] Hydroxyl group: an OH group linked via an O atom;

[0101] Cyano group: A CN group linked via a C atom;

[0102] Nitro group: A NO2 group linked via an N atom.

[0103] For the purposes of this invention, a bicyclic ring comprises two rings having at least one common ring atom. This term includes fused (fused-ring) systems where the two rings have two common adjacent ring atoms, spirocyclic systems where the rings have only one common ring atom, and bridging systems having at least three common ring atoms. Unless otherwise stated, a bicyclic ring can be carbocyclic, containing only carbon atoms as ring members, and heterocyclic, containing at least one heteroatom or heteroatom group typically selected from N, O, S, S(O), and S(O)₂ as a ring member. Further details are given below.

[0104] Polycyclic rings contain three or more rings, each ring having at least one ring atom common to at least one other ring in the polycyclic system. These rings can be fused, spirocyclic, or bridged; mixed systems (e.g., one ring spirocyclically bonded to a fused system, or a bridged system fused to another ring) are also possible. Unless otherwise specified, polycyclic rings can be carbocyclic, containing only carbon atoms as ring members, and heterocyclic, containing at least one heteroatom or heteroatom group typically selected from N, O, S, S(O), and S(O)₂ as a ring member. Further details are given below.

[0105] Z is 3, 4, 5, 6, 7, or 8-membered saturated, partially unsaturated, fully unsaturated, or aromatic monocyclic, bicyclic, or polycyclic, except for phenyl. It is formed by r carbon atoms (r = 1-8), k nitrogen atoms (k = 0-4), n sulfur atoms, and n oxygen atoms, wherein the sulfur atoms and carbon atoms bear n oxo groups (n = 0-2). If the sulfur atom contains 1 or 2 oxo groups, heteroatomic groups S(O) and S(O)2 will be generated as ring members. A carbon atom can, of course, bear only 0 or 1 oxo group.

[0106] Therefore, ring Z can be a carbon ring (i.e., containing only carbon atoms as ring members; here r is 3-8, k and n are 0) or a heterocyclic ring (i.e., also containing at least one N, O and / or S atom as ring members; r is therefore 1-7 here and at least one of n representing the number of O and S ring atoms and / or k is 1).

[0107] An unsaturated carbocyclic ring contains at least one C-C double bond. An unsaturated heterocyclic ring contains at least one C-C and / or CN and / or NN double bond. A partially unsaturated carbocyclic ring contains fewer than the maximum number of C-C double bonds allowed by the ring size. A partially unsaturated heterocyclic ring contains fewer than the maximum number of C-C and / or CN and / or NN double bonds allowed by the ring size. A fully (or maximally) unsaturated carbocyclic ring contains as many conjugated C-C double bonds as allowed by the ring size. However, phenyl is not included in the definition of Z. A fully (or maximally) unsaturated heterocyclic ring contains as many conjugated C-C and / or CN and / or NN double bonds as allowed by the ring size. Maximally unsaturated 5- or 6-membered heterocyclic rings are usually aromatic. Exceptions are maximally unsaturated 6-membered rings containing O, S, SO, and / or SO2 as ring members, such as non-aromatic pyrans and thiorans.

[0108] Examples of 3, 4, 5, 6, 7, or 8-membered saturated monocyclic carbon rings are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

[0109] Examples of partially or completely unsaturated monocyclic carbocyclic rings Z, 3, 4, 5, 6, 7, or 8, include cyclopropenyl, cyclopropenyl, cyclobutenyl, cyclobutenyl, cyclobutadienyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclopentenyl, cyclohex ... alkenyl, cyclohexyl-3-enyl, cyclohexyl-1,3-dienyl, cyclohexyl-1,4-dienyl, cyclohexyl-1,5-dienyl, cyclohexyl-2,4-dienyl, cyclohexyl-2,5-dienyl, cycloheptyl-1-enyl, cycloheptyl-2-enyl, cycloheptyl-3-enyl, cycloheptyl-4-enyl, cycloheptyl-1,3-dienyl, cycloheptyl-1,4-dienyl, cycloheptyl-1,5-dienyl, cycloheptyl-1,6-dienyl Cyclohepta-2,4-dienyl, cyclohepta-2,5-dienyl, cyclohepta-2,6-dienyl, cyclohepta-3,5-dienyl, cyclohepta-1,3,5-trienyl, cyclooct-1-enyl, cyclooct-2-enyl, cyclooct-3-enyl, cyclooct-4-enyl, cyclooct-5-enyl, cyclooct-6-enyl, cyclooct-7-enyl, cyclooct-1,3-dienyl, cyclooct-1,4-dienyl, cyclooct- 1,5-dienyl, cyclooctyl-1,6-dienyl, cyclooctyl-1,7-dienyl, cyclooctyl-2,4-dienyl, cyclooctyl-2,5-dienyl, cyclooctyl-2,6-dienyl, cyclooctyl-2,7-dienyl, cyclooctyl-3,5-dienyl, cyclooctyl-3,6-dienyl, cyclooctyl-1,3,5-trienyl, cyclooctyl-1,3,7-trienyl, cyclooctyl-2,4,6-trienyl, cyclooctatetraenyl.

[0110] Examples of 3, 4, 5, 6, 7, or 8-member saturated, partially unsaturated, completely unsaturated, or aromatic heterocyclic Z are as follows:

[0111] 3, 4, 5, 6, 7, or 8-membered saturated monocyclic heterocycles: for example, ethylene oxide-2-yl, thiocyclopropane-2-yl, aziridin-1-yl, aziridin-2-yl, oxetane-2-yl, oxetane-3-yl, thiocyclobutane-2-yl, thiocyclobutane-3-yl, 1-oxothiocyclobutane-2-yl, 1-oxothiocyclobutane-3-yl, 1,1-dioxothiocyclobutane-2-yl, 1,1-dioxothiocyclobutane-3-yl, azirane-1-yl, azirane-2-yl, azirane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophene-2-yl, tetrahydrothiophene-3-yl, 1-oxothiophene-2-yl, azirane-3-yl, 1-oxothiophene-2-yl, azirane-3-yl, azirane ... Tetrahydrothiophene-2-yl, 1,1-dioxotetrahydrothiophene-2-yl, 1-oxotetrahydrothiophene-3-yl, 1,1-dioxotetrahydrothiophene-3-yl, 1,3-dioxopentane-2-yl, 1,3-dioxopentane-4-yl, 1,3-dithiopentane-2-yl, 1,3-dithiopentane-4-yl, 1,3-oxothiohexacyclopentane-2-yl, 1,3-oxothiohexacyclopentane-4-yl, 1,3-oxothiohexacyclopentane-5-yl, pyrrolidine-1-yl, pyrrolidine-2-yl, pyrrolidine-3-yl, pyrazolidine-1-yl, pyrazolidine-3-yl, pyrazolidine-4-yl, pyrazolidine-5-yl, imidazolidinidine-1-yl, imidazolidinidine-2-yl, imidazolidinidine-4-yl 2-oxazolidinyl, 3-azolidinyl, 4-azolidinyl, 5-olazolidinyl, isozonil 2-oxazolidinyl, isozonil-2-yl 3-olazolidinyl, isozonil 4-azolidinyl, isozonil 1,2,4- thiazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidine-2-yl, isothiazolidine-3-yl, isothiazolidine-4-yl, isothiazolidine-5-yl, 1,2,4- diazolidin-3-yl, 1,2,4- Diazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,3,4- Diazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,2,4-triazolidin-1-yl, 1,2,4-triazolidin-3-yl, 1,2,4-triazolidin-4-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-di- Alkyl-2-yl, 1,3-di Alkyl-4-yl, 1,3-di Alkyl-5-yl, 1,4-di Alkyl-2-yl, Piperidin-1-yl, Piperidin-2-yl, Piperidin-3-yl, Piperidin-4-yl, Hexahydropyridazin-1-yl, Hexahydropyridazin-3-yl, Hexahydropyridazin-4-yl, Hexahydropyrimidin-1-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, 1,2,4-Hexahydrotriazin-1-yl, 1,2,4-Hexahydrotriazin-2-yl, 1,2,4-Hexahydrotriazin-3-yl, 1,2,4-Hexahydrotriazin-4-yl, 1,2,4-Hexahydrotriazin-4-yl Azin-5-yl, 1,2,4-hexahydrotriazin-6-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, azacycloheptane-1-, -2-, -3- or -4-yl, oxacycloheptane-2-, -3-, -4- or -5-yl, hexahydro-1,3-diaza yl, hexahydro-1,4-diaza alkyl, hexahydro-1,3-oxadiazine oxazepinyl, hexahydro-1,4-oxazepinyl [1,3]dioxepinyl, [1,4]dioxepinyl, oxocane, thiocane, azocanyl, [1,3]diazocanyl, [1,4]diazocanyl, [1,5]diazocanyl, [1,5]oxazocanyl, etc.

[0112] 3, 4, 5, 6, 7, or 8-membered partially unsaturated heteromonocyclic rings: 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 2,3-dihydrothiophen-2-yl, 2,3-dihydrothiophen-3-yl, 2,5-dihydrothiophen-2-yl, 2,5-dihydrothiophen-3-yl, 2-pyrrololin-2-yl, 2-pyrrololin-3-yl, 3-pyrrololin-2-yl, 3-pyrrololin-3-yl, 2-iso Azoline-3-yl, 3-iso Azoline-3-yl,4-iso Azoline-3-yl, 2-iso Azoline-4-yl,3-iso Azoline-4-yl,4-iso Azoline-4-yl, 2-iso Azoline-5-yl,3-iso Azoline-5-yl,4-iso Azoline-5-yl, 2-isothiazoline-3-yl, 3-isothiazoline-3-yl, 4-isothiazoline-3-yl, 2-isothiazoline-4-yl, 3-isothiazoline-4-yl, 4-isothiazoline-4-yl, 2-isothiazoline-5-yl, 3-isothiazoline-5-yl, 4-isothiazoline-5-yl, 2,3-dihydropyrazole-1-yl, 2,3-dihydropyrazole-2-yl, 2,3-dihydropyrazole -3-yl, 2,3-dihydropyrazole-4-yl, 2,3-dihydropyrazole-5-yl, 3,4-dihydropyrazole-1-yl, 3,4-dihydropyrazole-3-yl, 3,4-dihydropyrazole-4-yl, 3,4-dihydropyrazole-5-yl, 4,5-dihydropyrazole-1-yl, 4,5-dihydropyrazole-3-yl, 4,5-dihydropyrazole-4-yl, 4,5-dihydropyrazole-5-yl, 2,3-dihydro Azol-2-yl,2,3-dihydro Azol-3-yl,2,3-dihydro Azol-4-yl,2,3-dihydro Azol-5-yl,3,4-dihydro Azol-2-yl,3,4-dihydro Azol-3-yl,3,4-dihydro Azol-4-yl,3,4-dihydro Azol-5-yl,3,4-dihydro Azol-2-yl,3,4-dihydro Azol-3-yl,3,4-dihydro Azoxyl-4-yl, 3,6-dihydro-2H-pyran-2-, 3-, 4-, 5- or 6-yl, 3,4-dihydro-2H-pyran-2-, 3-, 4-, 5- or 6-yl, 3,6-dihydro-2H-thiaran-2-, 3-, 4-, 5- or 6-yl, 3,4-dihydro-2H-thiaran-2-, 3-, 4-, 5- or 6-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, 1,2,4-di- or tetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro[1H]aza -1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]aza -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]aza -1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]aza -1-, -2-, -3-, -4-, -5-, -6-, or -7-yl, tetrahydrooxetrazine heptatrienyl, such as 2,3,4,5-tetrahydro[1H]oxetrazine-2-, -3-, -4-, -5-, -6-, or -7-yl, 2,3,4,7-tetrahydro[1H]oxetrazine-2-, -3-, -4-, -5-, -6-, or -7-yl, 2,3,6,7-tetrahydro[1H]oxetrazine-2-, -3-, -4-, -5-, -6-, or -7-yl, tetrahydro-1,3-diaza Tetrahydro-1,4-diaza Tetrahydro-1,3-oxazine ,tetrahydro-1,4-oxazine Tetrahydro-1,3-dioxacycloheptatrienyl, tetrahydro-1,4-dioxacycloheptatrienyl, 1,2,3,4,5,6-hexahydroazacyclooctatetraene, 2,3,4,5,6,7-hexahydroazacyclooctatetraene, 1,2,3,4,5,8-hexahydroazacyclooctatetraene, 1,2,3,4,7,8-hexahydroazacyclooctatetraene, 1,2,3,4,5,6-hexahydro[1,5]diazacyclooctatetraene, 1,2,3,4,7,8-hexahydro[1,5]diazacyclooctatetraene, etc.

[0113] 3, 4, 5, 6, 7, or 8-membered maximally unsaturated (but non-aromatic) heteromonocyclic compounds: pyran-2-yl, pyran-3-yl, pyran-4-yl, thiaran-2-yl, thiaran-3-yl, thiaran-4-yl, 1-oxothiran-2-yl, 1-oxothiran-3-yl, 1-oxothiran-4-yl, 1,1-dioxothiran-2-yl, 1,1-dioxothiran-3-yl, 1,1-dioxothiran-4-yl, 2H- Azine-2-yl, 2H- Azine-3-yl, 2H- Azine-4-yl, 2H- Azine-5-yl, 2H- Azine-6-yl, 4H- Azine-3-yl, 4H- Azine-4-yl, 4H- Azine-5-yl, 4H- Azine-6-yl, 6H- Azine-3-yl, 6H- Azine-4-yl, 7H- Azine-5-yl, 8H- Azine-6-yl, 2H-1,3- Azine-2-yl, 2H-1,3- Azine-4-yl, 2H-1,3- Azine-5-yl, 2H-1,3- Azine-6-yl, 4H-1,3- Azine-2-yl, 4H-1,3- Azine-4-yl, 4H-1,3- Azine-5-yl, 4H-1,3- Azine-6-yl, 6H-1,3- Azine-2-yl, 6H-1,3- Azine-4-yl, 6H-1,3- Azine-5-yl, 6H-1,3- Azine-6-yl, 2H-1,4- Azine-2-yl, 2H-1,4- Azine-3-yl, 2H-1,4- Azine-5-yl, 2H-1,4- Azine-6-yl, 4H-1,4- Azine-2-yl, 4H-1,4- Azine-3-yl, 4H-1,4- Azine-4-yl, 4H-1,4- Azine-5-yl, 4H-1,4- Azine-6-yl, 6H-1,4- Azine-2-yl, 6H-1,4- Azine-3-yl, 6H-1,4- Azine-5-yl, 6H-1,4- Azine-6-yl, 1,4-di alken-2-yl, 1,4-oxothiacyclohexadien-2-yl, 1H-aza 1H-[1,3]-diaza 1H-[1,4]-diaza [1,3]diazacyclooctatetraene, [1,5]diazacyclooctatetraene, [1,5]diazacyclooctatetraene, etc.

[0114] 5 or 6-membered monocyclic aromatic heterocycles: for example, 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 1-pyrroleyl, 2-pyrroleyl, 3-pyrroleyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2- azole group, 4- azole, 5- azole group, 3-iso azole group, 4-iso azole group, 5-iso Azolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,3,4-triazol-3-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, 1,2,5- diazol-3-yl, 1,2,3- diazol-4-yl, 1,2,3- diazol-5-yl, 1,3,4- Diazol-2-yl, 1,2,5-thiadiazol-3-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-2-yl, 1,2,3,4-[1H]-tetrazol-5-yl, 1,2,3,4-[2H]-tetrazol-5-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1 -Oxopyridin-2-yl, 1-Oxopyridin-3-yl, 1-Oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,3,4-tetraazin-1-yl, 1,2,3,4-tetraazin-2-yl, 1,2,3,4-tetraazin-5-yl, etc.

[0115] The double rings have 4-8 members, with 5-8 members being preferred.

[0116] Examples of 5-8 member bicyclic spirocyclic saturated carbon rings include spiro[2.2]pentyl, spiro[2.3]hexyl, spiro[2.4]heptyl, spiro[3.3]heptyl, etc.

[0117] Examples of 5-8 bicyclic fused carbocyclic rings include bicyclic [3.1.0]hexyl, bicyclic [3.2.0]heptyl, bicyclic [3.3.0]octyl, 1,2,3,3a,4,5,6,6a-pentalenyl, bicyclic [4.2.0]octyl, etc.

[0118] Examples of 5-8 bicyclic bridging saturated carbon rings include bicyclic [1.1.1]pentyl, bicyclic [2.1.1]hexyl, bicyclic [2.2.1]heptyl, bicyclic [3.1.1]heptyl, bicyclic [2.2.2]octyl, bicyclic [3.2.1]octyl, etc.

[0119] An example of a 5-8 member polycyclic saturated carbon ring is a cubic alkyl group.

[0120] An example of a partially unsaturated bicyclic bridged carbon ring is a bicyclic [2.2.2]octyl-2-enyl.

[0121] Examples of 5-8 member saturated bicyclic fused heterocycles are as follows:

[0122]

[0123]

[0124] Examples of 5-8 member saturated bicyclic spirocyclic heterocyclic rings are as follows:

[0125]

[0126] An example of a 5-8 member saturated double-ring bridging heterocyclic ring is as follows:

[0127]

[0128] Examples of partially unsaturated double-ring bridged heterocyclic rings (5-8 members) are as follows:

[0129]

[0130] In the above structure, # indicates a connection point with the rest of the molecule. The connection point is not limited to the ring shown, but can be on either of the two rings, and can be on a carbon or nitrogen ring atom. If the ring carries one or more substituents, these substituents can be bonded to carbon and / or nitrogen ring atoms.

[0131] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d NCOR d and NC(O)OR d The unit has one carbon atom with p oxo groups.

[0132] Examples of 3-8 saturated monocyclic heterocyclic W-members include aziridinyl-2,2-diyl, ethylene oxide-2,2-diyl, thiocyclopropane-2,2-diyl, 1-oxo-thiocyclopropane-2,2-diyl, 1,1-dioxothiocyclopropane-2,2-diyl, aziridine-2,2-diyl, aziridine-3,3-diyl, oxacyclobutane-2,2-diyl, and oxacyclobutane-3... 3,2-diyl, thiohexacyclobutane-2,2-diyl, thiohexacyclobutane-3,3-diyl, 1-oxo-thiohexacyclobutane-2,2-diyl, 1-oxo-thiohexacyclobutane-3,3-diyl, 1,1-dioxo-thiohexacyclobutane-2,2-diyl, 1,1-dioxo-thiohexacyclobutane-3,3-diyl, pyrrolidine-2,2-diyl, pyrrolidine-3,3-diyl, tetrahydrofuran-2 2-Diyl, Tetrahydrofuran-3,3-Diyl, Tetrahydrothiophene-2,2-Diyl, Tetrahydrothiophene-3,3-Diyl, 1-Oxo-Tetrahydrothiophene-2,2-Diyl, 1-Oxo-Tetrahydrothiophene-3,3-Diyl, 1,1-Dioxo-Tetrahydrothiophene-2,2-Diyl, 1,1-Dioxo-Tetrahydrothiophene-3,3-Diyl, Pyrazolidine-3,3-Diyl, Pyrazolidine-4,4-Diyl, Imidazole Zolpidem-2,2-diyl, imidazolidin-4,4-diyl, 1,3-dioxolane-2,2-diyl, 1,3-dioxolane-4,4-diyl, 1,3-dithiopentane-2,2-diyl, 1,3-dithiopentane-4,4-diyl, 1,3-oxothiopyrazine-2,2-diyl, 1,3-oxothiopyrazine-4,4-diyl, 1,3-oxothiopyrazine-5,5-diyl 2,2-diol-azolidinyl 4,4-diol-azolidinyl AZolidine-5,5-diyl, isozonidine 3,3-diol, isozonidine-3,3-diol azole-4,4-diyl, isozonidine Isothiazolidine-5,5-diyl, thiazolyl-2,2-diyl, thiazolyl-4,4-diyl, thiazolyl-5,5-diyl, isothiazolidine-3,3-diyl, isothiazolidine-4,4-diyl, isothiazolidine-5,5-diyl, 1,2,4- diazolidine-3,3-diyl, 1,2,4- Diazolidine-5,5-diyl, 1,2,4-thiadiazolidine-3,3-diyl, 1,2,4-thiadiazolidine-5,5-diyl, 1,3,4- Diazolidine-2,2-diyl, 1,3,4-thiadiazolidine-2,2-diyl, 1,2,4-triazolidine-3,3-diyl, 1,2,4-triazolidine-5,5-diyl, tetrahydropyran-2,2-diyl, tetrahydropyran-3,3-diyl, tetrahydropyran-4,4-diyl, tetrahydrothiaran-2,2-diyl, tetrahydrothiaran-3,3-diyl, tetrahydrothiaran-4,4-diyl, 1- 2,2-oxotetrahydrothiaran-2,2-diyl, 1-oxotetrahydrothiaran-3,3-diyl, 1-oxotetrahydrothiaran-4,4-diyl, 1,1-dioxotetrahydrothiaran-2,2-diyl, 1,1-dioxotetrahydrothiaran-3,3-diyl, 1,1-dioxotetrahydrothiaran-4,4-diyl, piperidine-2,2-diyl, piperidine-3,3-diyl, piperidine-4,4-diyl, 1,3-diyl Alkyl-2,2-diyl, 1,3-di Alkyl-4,4-diyl, 1,3-di Alkyl-5,5-diyl, 1,4-di Alkyl-2,2-diyl, piperazine-2,2-diyl, hexahydropyridazine-3,3-diyl, hexahydropyridazine-4,4-diyl, hexahydropyrimidine-2,2-diyl, hexahydropyrimidine-4,4-diyl, hexahydropyrimidine-5,5-diyl, morpholine-2,2-diyl, morpholine-3,3-diyl, thiomorpholine-2,2-diyl, thiomorpholine-3,3-diyl, 1-oxo -Thiomorpholine-2,2-diyl, 1-oxo-thiomorpholine-3,3-diyl, 1,1-dioxothiomorpholine-2,2-diyl, 1,1-dioxothiomorpholine-3,3-diyl, azacycloheptane-2,2-, -3,3- or -4,4-diyl, oxocycloheptane-2,2-, -3,3- or -4,4-diyl, hexahydro-1,3-diaza -2,2-, -4,4- or -5,5-diyl, hexahydro-1,4-diaza -2,2-, -4,4- or -5,5-diyl, hexahydro-1,3-oxazine (oxazepin)-2,2-, -4,4-, -5,5-, -6,6- or -7,7-diyl, hexahydro-1,4-oxazepine -2,2-, -4,4-, -5,5-, -6,6- or -7,7-diyl, hexahydro-1,3-dioxepin-2,2-, -4,4- or -5,5-diyl, hexahydro-1,4-dioxepin-2,2-, -5,5- or -6,6-diyl, oxocan-2,2-, -3,3- or -4,4-diyl, thiocan-2,2-, -3,3- or -4,4-diyl, azocan-2,2-, -3,3- or -4,4-diyl, etc.; and other compounds containing a nitrogen atom as a ring member and R d COR d or C(O)OR d The aforementioned ring is replaced.

[0133] Examples of 3-8 partially unsaturated monocyclic heterocyclic W rings include 2,3-dihydrofuran-2,2-diyl, 2,3-dihydrofuran-3,3-diyl, 2,5-dihydrofuran-2,2-diyl, 2,3-dihydrothiophene-2,2-diyl, 2,3-dihydrothiophene-3,3-diyl, 2,5-dihydrothiophene-2,2-diyl, 1-oxo-2,3-dihydrothiophene-2,2-diyl, 1-oxo-2,3-dihydrothiophene-3,3-diyl, 1-oxo-2,5-dihydrothiophene-2,2-diyl, 1,1-dioxo-2,3-dihydrothiophene-2,2-diyl, 1,1-dioxo-2,3-dihydrothiophene-3,3-diyl, and 1,1-dioxo-2,5-dihydrothiophene-2,2-diyl. -diyl, 2,3-dihydro-1H-pyrrole-2,2-diyl, 2,3-dihydro-1H-pyrrole-3,3-diyl, 2,5-dihydro-1H-pyrrole-2,2-diyl, 1,3-dioxolane-2,2-diyl, 1,3-dioxolane-4,4-diyl, 1,3-dithiopentane-2,2-diyl, 1,3-dithiopentane-4,4-diyl, 1,3-oxothiopyrazine-2,2-diyl, 1,3-oxothiopyrazine-4,4-diyl, 1,3-oxothiopyrazine-5,5-diyl, 2,3-dihydro-1H-pyrazole-3,3-diyl, 2,5-dihydro-1H-imidazol-2,2-diyl, 2,5-dihydro-1H-imidazol-5,5-diyl, 2,3-dihydro azole-2,2-diyl, 2,5-dihydro azole-2,2-diyl, 2,5-dihydro azole-5,5-diyl, 4,5-dihydro azole-4,4-diyl, 4,5-dihydro azole-5,5-diyl, 2,3-dihydroisocyanate azole-3,3-diyl, 2,5-dihydroisocyanate 2,2-dimethyl-4,5-dihydroisocyanate azole-4,4-diyl, 4,5-dihydroisocyanate 2,5-Dihydrothiazole-5,5-diyl, 2,3-dihydrothiazole-2,2-diyl, 2,5-dihydrothiazole-2,2-diyl, 2,5-dihydrothiazole-5,5-diyl, 4,5-dihydrothiazole-4,4-diyl, 4,5-dihydrothiazole-5,5-diyl, 2,3-dihydroisothiazole-3,3-diyl, 2,5-dihydroisothiazole-2,2-diyl, 4,5-dihydroisothiazole-4,4- Diyl, 4,5-dihydroisothiazol-5,5-diyl, 3,6-dihydro-2H-pyran-2,2-diyl, 3,6-dihydro-2H-pyran-3,3-diyl, 3,6-dihydro-2H-pyran-6,6-diyl, 3,4-dihydro-2H-pyran-4,4-diyl, 3,4-dihydro-2H-pyran-5,5-diyl, 3,4-dihydro-2H-pyran-6,6-diyl 3,6-dihydro-2H-thiaran-2,2-diyl, 3,6-dihydro-2H-thiaran-3,3-diyl, 3,6-dihydro-2H-thiaran-6,6-diyl, 3,4-dihydro-2H-thiaran-4,4-diyl, 3,4-dihydro-2H-thiaran-5,5-diyl, 3,4-dihydro-2H-thiaran-6,6-diyl, 1,2,3,4-tetrahydropyridine-2, 2-Diyl, 1,2,3,4-Tetrahydropyridine-3,3-diyl, 1,2,3,4-Tetrahydropyridine-4,4-diyl, 1,2,3,6-Tetrahydropyridine-2,2-diyl, 1,2,3,6-Tetrahydropyridine-3,3-diyl, 1,2,3,6-Tetrahydropyridine-6,6-diyl, 1,2-Dihydropyridine-2,2-diyl, 1,4-Dihydropyridine-4,4-diyl, etc.

[0134] Examples of 3-8 saturated and partially unsaturated bicyclic heterocycles W are the saturated and partially unsaturated bicyclic heterocycles shown above, except that in the case of ring W exemplified here, there are two connection points with the rest of the molecule on the same carbon ring atom.

[0135] The preferred embodiments of the present invention described below should be understood as being preferred either independently or in combination with each other.

[0136] One embodiment of the present invention relates to a compound of formula (I):

[0137]

[0138] The substituents have the following meanings:

[0139] R 1It can be hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0140] R 2 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0141] R 3 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0142] R 4 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, or C2-C3 haloalkynyl.

[0143] R 5 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0144] R 6 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0145] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic rings W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NCOR dThe unit, in which one carbon atom carries p oxo groups and is surrounded by n R groups. g replace;

[0146] R 9 It can be hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C3 alkoxy-C1-C3 alkoxy.

[0147] X is the key (X 0 () or selected from the following divalent units: (X) 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ):

[0148]

[0149] R 10 -R 15 Each of these can be independently represented as hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyanide, or CO2R. e CONR b R d R a Or C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, hydroxyl and cyano; or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and C1-C2 alkoxy;

[0150] Y represents hydrogen, cyano, hydroxyl, or Z.

[0151] Or C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 The alkynyl group is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONRb R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e ;

[0152] Z is a 3, 4, 5, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring, excluding phenyl groups, and is formed by r carbon atoms, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2R e CONR b R h S(O) n R a SO2NR b R d SO2NR b COR e COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNRb R e POR f R f and C(R) b ) = NOR e R b R c R e and R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0153] R a It is a C1-C6 alkyl, C2-C4 alkynyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl and C1-C3 alkoxy;

[0154] R b For hydrogen or R a ;

[0155] R c The groups are fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, and S(O). n R a Or C1-C6 alkoxy, C3-C6 alkenoxy or C3-C6 alkynoxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0156] R d It is hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0157] R e For example, R d Defined;

[0158] R f It is a C1-C3 alkyl or C1-C3 alkoxy;

[0159] R g The groups are halogen, nitro, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, and C1-C3 alkylsulfonyl.

[0160] Rh It is hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0161] m can be 0, 1, 2, 3, 4, or 5;

[0162] n is 0, 1, or 2;

[0163] p is 0 or 1;

[0164] q is 1, 2, 3, 4, 5, 6, or 7;

[0165] r is 1, 2, 3, 4, 5, or 6;

[0166] u is 0, 1, or 2;

[0167] v can be 0, 1, 2, or 3;

[0168] w is 0, 1, or 2;

[0169] x is 0, 1, or 2;

[0170] This includes its agricultural salts, and in the case of compounds of formula (I) having a carboxyl group (COOH), its amides, esters or thioesters.

[0171] According to the specific implementation scheme, the compound of formula (I) is wherein the condition for application is that at least one of u, v, w and x is not 0 and therefore ring W is heterocyclic (in which case q can be only 1, 2, 3, 4, 5 or 6).

[0172] According to a particular embodiment of the invention, compounds of formula (I) are also preferred, wherein the variables have the following meanings, either independently or in combination:

[0173] The preferred compound according to the present invention is the compound of formula (I), wherein R 1 It is selected from hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy-C1-C3 alkyl, and C1-C3 alkoxy.

[0174] The preferred compound according to the present invention is the compound of formula (I), wherein R 1 It is selected from hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl and C1-C3 alkoxy-C1-C3 alkyl.

[0175] According to the present invention, a preferred compound is a compound of formula (I), wherein R 1 Selected from hydrogen, methyl, and methoxymethyl.

[0176] In particular, R 1 It is hydrogen.

[0177] A further preferred compound according to the present invention is a compound of formula (I), wherein R 2 It is selected from hydrogen, halogenated hydroxyl, cyano and C1-C3 alkyl.

[0178] The preferred compound according to the present invention is the compound of formula (I), wherein R 2 It is selected from hydrogen, halogens and C1-C3 alkyl groups, especially from hydrogen and halogens.

[0179] According to the present invention, a preferred compound is a compound of formula (I), wherein R 2 It is selected from hydrogen, fluorine, chlorine and methyl, especially from hydrogen, fluorine and chlorine, and very especially from H and F.

[0180] In particular, R 2 It is hydrogen.

[0181] A further preferred compound according to the present invention is a compound of formula (I), wherein R 3 It is selected from hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy.

[0182] Alternatively, according to the present invention, a further preferred compound is a compound of formula (I), wherein R 3 Selected from hydrogen, halogen, cyano, nitro, and C1-C3 alkyl. Alternatively, according to the present invention, a further preferred compound is a compound of formula (I), wherein R 3 It is selected from hydrogen, halogen, hydroxyl, cyano and C1-C3 alkyl.

[0183] The preferred compound according to the present invention is the compound of formula (I), wherein R 3 It is selected from halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy.

[0184] According to the present invention, even more preferably, the compound of formula (I) is a compound, wherein R 3 Selected from halogens and C1-C3 haloalkoxy groups.

[0185] In particular, R 3 It is selected from halogens, methyl, ethyl, methoxy and halomethoxy, and very particularly from fluorine, chlorine, cyano and trifluoromethoxy.

[0186] In particular, R 3 It is hydrogen, halogen, cyano or C1-C3 haloalkoxy, more particularly halogen, and very particularly chlorine or fluorine.

[0187] A further preferred compound according to the present invention is a compound of formula (I), wherein R 4 Selected from hydrogen and halogens.

[0188] According to the present invention, a preferred compound is a compound of formula (I), wherein R 4 It is selected from hydrogen, fluorine, chlorine and bromine.

[0189] In particular, R 4 It can be hydrogen, fluorine, or chlorine, with hydrogen being particularly noteworthy.

[0190] A further preferred compound according to the present invention is a compound of formula (I), wherein R 5 It is selected from hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy.

[0191] A further preferred compound according to the present invention is a compound of formula (I), wherein R 5 It is selected from hydrogen, halogen, hydroxyl, cyano and C1-C3 alkyl.

[0192] Alternatively, other preferred compounds according to the invention are compounds of formula (I), wherein R 5 Selected from hydrogen, halogen, hydroxyl, cyano, and C1-C3 alkyl. Alternatively, other preferred compounds according to the invention are compounds of formula (I), wherein R 5 It is selected from hydrogen, halogen, hydroxyl, cyano, and C1-C3 alkyl.

[0193] The preferred compound according to the present invention is the compound of formula (I), wherein R 5 It is selected from hydrogen, halogens and C1-C3 alkyl groups.

[0194] According to the present invention, even more preferably, the compound of formula (I) is a compound, wherein R 5 Selected from hydrogen and halogens.

[0195] According to the present invention, a preferred compound is a compound of formula (I), wherein R 5 It is selected from hydrogen, halogens and methyl, especially hydrogen, chlorine and fluorine.

[0196] In particular, R 5 It is hydrogen or halogen, very specifically hydrogen, chlorine or fluorine.

[0197] A further preferred compound according to the present invention is a compound of formula (I), wherein R 6 It is selected from hydrogen, halogens and C1-C3 alkyl groups.

[0198] A more preferred compound according to the present invention is a compound of formula (I), wherein R 6 Selected from hydrogen and halogens.

[0199] According to the present invention, a preferred compound is a compound of formula (I), wherein R 6 It is selected from hydrogen, fluorine, chlorine and methyl, especially hydrogen, chlorine or fluorine.

[0200] In particular, R 6 It is hydrogen.

[0201] According to the present invention, a preferred compound is a compound of formula (I), wherein R 9 Selected from hydrogen and C1-C3 alkyl groups. Specifically, R 9 It can be hydrogen, methyl, or ethyl, with hydrogen being particularly noteworthy.

[0202] Preferred embodiments of the present invention relate to compounds of formula (I), wherein the substituent R 1 and R 9 It has the following meaning: R 1 It is hydrogen, methyl, or methoxymethyl; and R 9 It is hydrogen or C1-C4 alkyl.

[0203] A more preferred embodiment of the present invention relates to a compound of formula (I), wherein the substituent R 1 and R 9 It has the following meaning: R 1 It is hydrogen; and R 9 It is hydrogen or C1-C4 alkyl.

[0204] In particular, R 1 and R 9 It is hydrogen.

[0205] Another preferred embodiment of the invention relates to a compound of formula (I), wherein the substituent R 2 and R 6 It has the following meaning: R 2 It is hydrogen, halogen, or C1-C3 alkyl; and R 6 It is hydrogen, halogen, or C1-C3 alkyl.

[0206] Another preferred embodiment of the invention relates to a compound of formula (I), wherein the substituent R 2 and R 6 It has the following meaning: R 2 It is hydrogen or halogen; and R 6 It is hydrogen or halogen.

[0207] In particular, R 2 and R 6 It is hydrogen.

[0208] Another preferred embodiment of the invention relates to a compound of formula (I), wherein the substituent R 3 and R 5 It has the following meaning: R 3It is hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy; especially halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy, particularly halogen or C1-C3 haloalkoxy; and R 5 It is hydrogen, halogen, hydroxyl, cyano or C1-C3 alkyl, especially hydrogen, halogen or C1-C3 alkyl, particularly hydrogen or halogen.

[0209] A more preferred embodiment of the present invention relates to a compound of formula (I), wherein the substituent R 3 and R 5 It has the following meaning: R 3 It is a halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy; and R 5 It is hydrogen, halogen, or C1-C3 alkyl.

[0210] Even more preferred embodiments of the present invention relate to compounds of formula (I), wherein the substituent R 3 and R 5 It has the following meaning: R 3 It is a halogen, cyano, or C1-C3 haloalkoxy group, especially fluorine, chlorine, cyano, or trifluoromethoxy; and R 5 It is hydrogen or halogen, especially hydrogen, chlorine or fluorine.

[0211] via R 7 and R 8 In the ring formed together with the carbon atoms they are bonded to, the sum of u+v+w+x is preferably 1 or 2.

[0212] Another preferred embodiment of the present invention, W1, relates to a compound of formula (I), wherein R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, w sulfur atoms, v nitrogen atoms, and x atoms selected from NR. d and NC(O)OR d The unit, wherein the ring is bounded by n groups R g And p oxo groups are substituted, and R is wherein d R g , q, u, w, v, x, and p have the meanings defined herein, and especially the meanings preferred herein.

[0213] Another preferred embodiment of the present invention, W2, relates to a compound of formula (I), wherein R 7 and R 8Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 4-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, w sulfur atoms, v nitrogen atoms, and x atoms selected from NR. d and NC(O)OR d The unit, wherein the ring is bounded by n groups R g And p oxo groups are substituted, and R is wherein d R g , q, u, w, v, x, and p have the meanings defined herein, and especially the meanings preferred herein.

[0214] Another preferred embodiment of the present invention, W3, relates to a compound of formula (I), wherein R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3, 4, 5, or 6-membered monocyclic heterocycles W or 6, 7, or 8-membered bicyclic heterocycles W. In addition to the carbon atom, the ring contains q carbon atoms, u oxygen atoms, w sulfur atoms, v nitrogen atoms, and x atoms selected from NR. d and NC(O)OR d The unit, wherein the ring is bounded by n groups R g And p oxo groups are substituted, and R is wherein d R g , q, u, w, v, x, and p have the meanings defined herein, and especially the meanings preferred herein.

[0215] Examples of 3-8 member monocyclic or bicyclic W according to implementation scheme W1 are the following rings, wherein the nitrogen atom, which is a ring member and not part of a double bond, optionally carries a substituent R. d or C(O)OR d Furthermore, the ring can be further divided by n groups R. g Substitution and / or one or two CH2 ring member groups may be substituted by p C=O groups; and / or sulfur atoms that are ring members but not part of a double bond may be substituted by one or two oxo groups, thus producing heteroatom groups S(O) and S(O)2 as ring members, where n and R g It has the meaning as defined herein, and in particular the meaning of preferred:

[0216]

[0217]

[0218] The arrows indicate bonds to two C(O) groups.

[0219] Another preferred embodiment W4 of the present invention relates to a compound of formula (I) as defined in the foregoing embodiments W1-W3, wherein the variables u, v, w, and x have the following meanings:

[0220] -u is 1 or 2, v is 0, w is 0 and x is 0; or

[0221] -u is 0 or 1, v is 1, w is 0 and x is 0; or

[0222] -u is 0 or 1, v is 0, w is 1 and x is 0; or

[0223] -u is 0, v is 0, w is 0 and x is 1.

[0224] Another preferred embodiment of the invention, W5, relates to a compound of formula (I) as defined in the aforementioned embodiment W4, wherein the variables q, n, and p have the following meanings:

[0225] q is 1, 2, 3, 4, 5, 6 or 7, preferably 1, 2, 3, 4, 5 or 6, more preferably 1, 2, 3 or 4, especially 1, 2 or 3, and

[0226] n is 0, 1, or 2, more preferably 0 or 1; and

[0227] p is 0 or 1, preferably 0.

[0228] Preferred examples of single-ring or double-ring W according to embodiments W1-W5 are the following rings, wherein q is 1, 2, 3, 5 or 6, u is 0, 1 or 2, v is 0 or 1, w is 0 or 1, x is 0 or 1, p is 0, n is 0, 1 or 2, and R d If present, it is methyl or tert-butyl, and R g If present, it is methyl, ethyl, or chloromethyl, or both R. g Bonded to the same carbon atom, forming a methylene group (=CH2). The arrow or # indicates a bond with an adjacent carbonyl carbon atom.

[0229]

[0230] The arrow and # indicate a bond with two C(O) groups.

[0231] A particularly preferred example of a single or double ring W according to embodiments W1-W5 is the following ring, wherein q is 1, 2, 3, 5 or 6, u is 0, 1 or 2, v is 0 or 1, w is 0 or 1, x is 0 or 1, p is 0 or 1, n is 0, 1 or 2, and R d If it exists, it is tert-butyl, R g If present, it is a methyl group, or two R groups. gBonded to the same carbon atom, forming a methylene group (=CH2), # indicates a bond with an adjacent carbonyl carbon atom:

[0232]

[0233]

[0234] Another preferred embodiment of the present invention, W6, relates to a compound of formula (I), wherein R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3, 4, 5, or 6-membered monocyclic heterocycles W or 6, 7, or 8-membered bicyclic heterocycles W. In addition to the carbon atom, the ring contains q carbon atoms, u oxygen atoms, w sulfur atoms, v nitrogen atoms, and x atoms selected from NR. d and NC(O)OR d The unit, wherein the ring is bounded by n groups R g Replace, and where R d R g q, u, w, v, x, and n have the meanings defined herein, and especially the meanings preferred herein. In this embodiment, q, u, w, v, and x have the following meanings in particular:

[0235] q is 1, 2, 3, 4, 5, or 6, preferably 1, 2, 3, 4, or 5, more preferably 1, 2, 3, or 4, especially 2 or 3, and

[0236] u is 0, 1, or 2.

[0237] w is 0 or 1.

[0238] v is 0 or 1, and

[0239] x is 0 or 1, and

[0240] n is 0, 1, or 2.

[0241] Preferably, u+v+w+x = 1 or 2.

[0242] Another preferred embodiment of the present invention, W7, relates to a compound of formula (I), wherein R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3, 4, 5, or 6-membered monocyclic heterocycles W or 6, 7, or 8-membered bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms and u oxygen atoms, wherein the ring is bounded by n groups R. g Replace, and among them

[0243] q is 1, 2, 3, 4, 5, or 6, and

[0244] u is 0 or 1, and

[0245] R g And n has the meaning defined in this paper, especially the meaning preferred in this paper.

[0246] Another preferred embodiment of the present invention, W8, relates to a compound of formula (I), wherein R 7 and R 8 Together with the carbon atoms they are bonded to, they form a saturated or partially unsaturated 4-5 member heterocycle W. Besides the carbon atom, the ring contains q carbon atoms and u oxygen atoms, wherein the ring is bound by n groups R. g Replace, and among them

[0247] q is 2 or 3, and

[0248] u is 0 or 1, and

[0249] R g And n has the meaning defined in this paper, especially the meaning preferred in this paper.

[0250] Another preferred embodiment of the present invention, W9, relates to a compound of formula (I), wherein R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 4-5 member heterocycles W, selected from the following ring structures, which may be further bonded by n groups R. g Replacement, where n is 0, 1, or 2, preferably 0 or 1, especially 0, and where each R g It has one of the meanings defined herein, especially one of the preferred meanings:

[0251]

[0252] Another preferred embodiment of the invention, W10, relates to compounds of formula (I), particularly compounds according to embodiments W1-W9, which contain x atoms selected from NR. d NCOR d and NC(O)OR d The heterocyclic ring W of the unit, wherein each substituent R d The components are independently selected from hydrogen and C1-C6 alkyl groups, preferably hydrogen and C1-C4 alkyl groups, especially hydrogen and C1-C3 alkyl groups, such as hydrogen, tert-butyl, isopropyl, ethyl and methyl.

[0253] Another preferred embodiment of the invention, W11, relates to compounds of formula (I), particularly compounds according to embodiments W1-W10, wherein each substituent R g If present, it is independently selected from C1-C3 alkyl or C1-C3 haloalkyl, especially methyl, ethyl, chloromethyl and fluoromethyl, particularly methyl, or two R gIt bonds with the same carbon atom to form a methylene group (=CH2).

[0254] Compounds of formula (I) of the present invention may contain a stereoisomeric center (*), depending on the structure of ring W (which must not contain a mirror axis to allow for the presence of R). 7 and R 8 (where the carbon atom becomes the stereoisomer center), as shown in the following equation:

[0255]

[0256] Therefore, if with R 7 and R 8 If the carbon atom that bonds to form ring W is the stereoisomer center, then the compound of formula (I) exists in two stereoisomeric forms (if no other stereoisomer center exists; otherwise, the compound of formula (I) exists in more than two stereoisomeric forms; more precisely, in 2 n There are 10 stereoisomers, where n is the number of stereoisomer centers in the molecule (provided that no intermediate form exists). All stereoisomers and mixtures thereof are also part of this invention.

[0257] In the compound of formula (I), X is selected from the bond (X). 0 () or selected from the following divalent units: (X) 1 ), (X 2 ),

[0258]

[0259] Preferred embodiments of the present invention relate to formula (IX) 0 ) compounds, where X is a bond (X 0 ):

[0260]

[0261] Another preferred embodiment of the present invention relates to formula (IX) 1 ) compound, where X is (X 1 ), and within which (X) 1 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0262]

[0263] Another preferred embodiment of the present invention relates to formula (IX) 2 ) compound, where X is (X 2 ), and within which (X) 2 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0264]

[0265] Another preferred embodiment of the present invention relates to formula (IX) 3 ) compound, where X is (X 3 ), and within which (X) 3 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0266]

[0267] Another preferred embodiment of the present invention relates to formula (IX) 4 ) compound, where X is (X 4 ), and within which (X) 4 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0268]

[0269] Another preferred embodiment of the present invention relates to formula (IX) 5 ) compound, where X is (X 5 ), and within which (X) 5 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0270]

[0271] Another preferred embodiment of the present invention relates to formula (IX) 6 ) compound, where X is (X 6 ), and within which (X) 6 The orientation of the ) is shown in the figure. The left arrow indicates the bond with the adjacent nitrogen, and the right arrow indicates the bond with the adjacent group Y:

[0272]

[0273] A further preferred compound according to the present invention is a compound of formula (I), wherein X is selected from bond (X). 0 ) or the following formula (X) 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) or (X 6One of the divalent units of ) is: CH2, CH2CH2, CH(CH3), CH2CH2CH2, CH(CH2CH3), CH(CH3)CH2, C(CH3)2, C(CH3)2CH2, C(iPr)CH3, CH(CH2iPr)CH2, CH2CH=CH, C(CH3)2C≡C, CH(CF3)CH2, CH(CH3)CH2O, CH2CH2O, CH(cPr)CH2O, CH(CH2OCH3), CH(CH2CH2SCH3), CH(COOH), CH(COOCH3), CH(COOH)CH2, CH(COOCH3)CH2, CH2COH(CF3), CH(CONHCH3), CH(CONHCH3)CH2 and CH2CH2CONHCH2.

[0274] iPr is isopropyl; cPr is cyclopropyl.

[0275] Specifically, X is the key (X 0 ) or divalent unit (X) 6 ).

[0276] Preferably, the substituent R 10 -R 15 Each of the following groups appears independently and independently: hydrogen, fluorine, chlorine, bromine, hydroxyl, cyanide, and CO2R. e CONR b R d Alternatively, it could be C1-C6 alkyl, C3-C5 cycloalkyl, or C2-C6 alkenyl, wherein each of the last three aliphatic or alicyclic groups is replaced by m fluorine groups; or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenoxy, or C3-C6 alkynoxy, wherein the aliphatic or alicyclic structural portions of each of the last four groups are replaced by m fluorine groups, and wherein m and R... e R b and R d It has the meaning as defined herein, especially the meaning of preferred.

[0277] More preferably, the substituent R 10 -R 15 The elements that appear independently of each other and each time are hydrogen, fluorine, chlorine, and CO2R. e CONR b R d Or a C1-C6 alkyl group, which is substituted with m fluorine groups, or a C1-C6 alkoxy group, which is substituted with m fluorine groups, wherein m, R e R b and R d It has the meaning as defined herein, especially the meaning of preferred.

[0278] In particular, the substituent R 10 -R 15 Each of these elements, and each occurrence of each element, is independently hydrogen, fluorine, chlorine, C1-C4 alkyl, C1-C3 alkoxy, or CO2R. e In particular, hydrogen, methyl, ethyl, or methoxy; especially hydrogen or methyl, and wherein R e It has one of the meanings defined herein, and in particular one of the preferred meanings.

[0279] A further preferred compound according to the present invention is a compound of formula (I), wherein Y is selected from hydrogen, cyano, hydroxyl, Z, or C1-C. 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 The alkynyl group is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, Z, CO2R. e CONR b R h and CONR e SO2R a .

[0280] According to the present invention, a preferred compound is a compound of formula (I), wherein Y is selected from hydrogen, cyano, hydroxyl, Z, or C1-C. 12 Alkyl groups and C3-C8 cycloalkyl groups, each substituted with m groups selected from the following: fluorine, CO2R e CONR b R h and CONR e SO2R a .

[0281] Preferred embodiment Y1 of the present invention relates to a compound of formula (I) according to the invention, wherein Y is selected from C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl or C2-C8 alkynyl, each substituted by m groups selected from: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NRb COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e Where m, n, ZR a R b R e R d R f and R h It has the meaning as defined herein, especially the meaning of preferred.

[0282] Another preferred embodiment of the present invention, Y1-1, relates to a compound of formula (I) according to the invention, wherein Y is selected from C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, and C2-C8 alkynyl, each being m-terminated by m-terminated groups selected from fluorine, OR d Z, CO2R e CONR b R h and CONR e SO2R a The groups are substituted, wherein m and ZR are... a R b R e R d and R h It has the meaning as defined herein, especially the meaning of preferred.

[0283] Another preferred embodiment of the present invention, Y1-2, relates to a compound of formula (I) according to the invention, wherein Y is selected from C1-C8 alkyl and C2-C8 alkenyl groups, each being separated by a compound selected from CO2R. e CONR b R h CONR e SO2R a The group of Z is substituted and optionally replaced by an OR d Substituent substitution, where Z and R a R b Re R d and R h It has the meaning as defined herein, and especially the preferred meaning. Preferably, it carries the CO2R group. e .

[0284] Preferred examples of structural portion Y according to embodiments Y1-2 are selected from the following structures, wherein the dash on the left indicates a bond with the remainder of the molecule of compound (I), and the dash on the right indicates a bond with a substituent CO2R as defined herein. e CONR b R h or CONR e SO2R a The bond, and where the substituent -OCH3 is a substituent OR if present. d : -CH2-, -CH2CH2-, -CH(CH3)-, -CH2CH2CH2-, -CH(CH2CH3)-, -CH(CH3)CH2-, -C(CH3)2-, -C(CH3)2CH2-, -C(iPr)CH3-, -CH(CH2iPr)CH2-, -CH2CH=CH-, -C(CH3)( CH2OCH3)-, -C(CH3)CH2CH2-, -C(CH3)2CH=CH-, -CH2CH2CH2CH2-, -CH(CH3)C(CH3)2-, -CH2CH(CH3)-, -CH2CH(OCH3)CH2-, -CH2CH(CH3)CH2-, and -C(CH3)(CH2CH3)-. iPr is isopropyl.

[0285] In the context of this implementation scheme Y1-2, particularly preferred examples of structural portion Y are the following structures: -CH2-, -CH2CH2-, -CH(CH3)-, -CH2CH2CH2-, -CH(CH3)CH2-, -C(CH3)2-, -C(CH3)2CH2-, -C(CH3)(CH2OCH3)-, -C(CH3)CH2CH2-, -C(CH3)2CH=CH-, -CH2CH2CH2CH2-, -CH(CH3)C(CH3)2-, -CH2CH(CH3)-, -CH2CH(OCH3)CH2-, -CH2CH(CH3)CH2- and -C(CH3)(CH2CH3)-.

[0286] Another preferred embodiment of the invention, Y1-3, relates to compounds of formula (I) according to the invention, wherein Y is a C2-C8 ynyl group, particularly a C2-C4 ynyl group.

[0287] A preferred example of structural part Y according to implementation scheme Y1-3 is propargyl (-CH2-C≡CH).

[0288] Another preferred embodiment of the present invention relates to a compound of formula (I), wherein the group Y is Z.

[0289] The preferred compound according to the present invention is a compound of formula (I), wherein Z is selected from 3-8 saturated, partially unsaturated, or aromatic monocyclic, bicyclic, or polycyclic compounds, excluding phenyl groups, and is formed by r carbon atoms, n oxygen atoms, n sulfur atoms, and k nitrogen atoms, each surrounded by m atoms selected from CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f The group is substituted, wherein R is a group that is substituted for R. a R b R c R e R f and R h It has the meaning as defined herein, especially the meaning of preferred.

[0290] A more preferred compound according to the present invention is a compound of formula (I), wherein Z is selected from 3-8 saturated or partially unsaturated monocyclic, bicyclic, or polycyclic rings, formed by r carbon atoms, n oxygen atoms, n sulfur atoms, and k nitrogen atoms, each surrounded by m atoms selected from CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f The group is substituted, wherein R is a group that is substituted for R. a R b R c R e R f and R h It has the meaning as defined herein, especially the meaning of preferred.

[0291] A representative example of a 3-8 member ring Z as defined in this paper is the following structure, which can be further divided by m members selected from CO2R as defined in this paper. e CONR b R h CONR e SO2R a Rb R c R e and R f Group substitutions, indicated by arrows or #, represent bonds with the rest of the compound (I) molecule:

[0292]

[0293]

[0294] According to the invention, a preferred compound is a compound of formula (I), wherein Z is selected from 4 or 5 saturated or partially unsaturated rings, which are formed by r carbon atoms and n oxygen atoms, each surrounded by m atoms selected from CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f The group is substituted.

[0295] According to the invention, a preferred compound is a compound of formula (I), wherein Z is selected from a 5-member saturated or partially unsaturated ring, which is formed by 4 carbon atoms and 1 oxygen atom, each surrounded by m atoms selected from CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f The group is substituted.

[0296] The above is formed by 4 carbon atoms and 1 oxygen atom, each composed of m atoms selected from CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f A representative example of a 5-membered saturated or partially unsaturated ring substituted with a group is the following structure, where the wavy line indicates the bond with the rest of the molecule of formula (I) (i.e., with X or NR). 9 The key (if X is a key), and the arrow indicates a bond with any mentioned substituent:

[0297]

[0298] The above is formed by 4 carbon atoms and 1 oxygen atom, each composed of m atoms selected from CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f Preferred examples of a group-substituted 5-membered saturated or partially unsaturated ring are the following structures, where the wavy line indicates the bond with the remainder of the molecule of formula (I) (i.e., with X or NR). 9 The bond (if X is a bond), and the arrow or # indicates a bond with any mentioned substituent, preferably with CO2R. e The key:

[0299]

[0300] According to the present invention, a preferred compound is a compound of formula (I), wherein Z is selected from a 5-member saturated or partially unsaturated ring, formed by 4 carbon atoms and 1 oxygen atom, each surrounded by m atoms selected from CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f The group is substituted.

[0301] The above is formed by 5 carbon atoms, each of which is composed of m atoms selected from CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f A representative example of a 5-membered saturated or partially unsaturated ring substituted with a group is the following structure, where the wavy line indicates the bond with the rest of the molecule of formula (I) (i.e., with X or NR). 9 The key (if X is a key), and the arrow or # indicates a key with any mentioned substituent:

[0302]

[0303] The above is formed by 5 carbon atoms, each of which is composed of m atoms selected from CO2R. e CONR b R h CONR eSO2R a R b R c R e and R f Preferred examples of a group-substituted 5-membered saturated or partially unsaturated ring are the following structures, where the wavy line indicates the bond with the remainder of the molecule of formula (I) (i.e., with X or NR). 9 The bond (if X is a bond), and the arrow or # indicates a bond with any mentioned substituent, preferably with CO2R. e The key:

[0304]

[0305] Preferred examples of the structural moiety Z of the compound (I) according to the invention are the following structures Z.1-Z.24, each consisting of m molecules selected from CO2R as defined above. e CONR b R h S(O) n R a SO2NR b R d SO2NR b COR e COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e R b R c R e and R f The group substitution, wherein in each case the wavy line (wave line) indicates the substitution with X or NR. 9The bond, if X is a bond, #(1) and #(2) represent bonds with any of the above substituents, especially with CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f The key:

[0306]

[0307]

[0308] In the particularly preferred structures Z.1-Z.24, #(1) in each case represents the substituent CO2R. e CONR b R h or CONR e SO2R a The bond, especially with CO2R e The bond, #(2) indicates the bond with substituent R. b R c R e or R f The bonds, especially those with hydrogen, methyl or fluorine (however, in the case of Z.17, especially those with hydrogen or methyl).

[0309] Particularly preferred examples of the structural moiety Z of the compound (I) according to the invention are the following structures Z.1-Z.7, Z.9, Z.12 and Z.15-Z.17, each being m molecules selected from CO2R as defined herein. e CONR b R h S(O) n R a SO2NR b R d SO2NR b COR e COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR bSO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e R b R c R e and R f The group substitution, wherein in each case the wavy line (wave line) indicates the substitution with X or NR. 9 The bond, if X is a bond, #(1) and #(2) represent bonds with any of the above substituents, especially with CO2R. e CONR b R h CONR e SO2R a R b R c R e and R f The key:

[0310]

[0311]

[0312] In the particularly preferred structures Z.1-Z.7, Z.9, Z.12 and Z.15-Z.17, in each case #(1) represents the substituent CO2R. e CONR b R h or CONR e SO2R a The bond, especially with CO2R e The bond, #(2) indicates the bond with substituent R. b R c R e or R f The bonds, especially those with hydrogen, methyl or fluorine (however, in the case of Z.17, especially those with hydrogen or methyl).

[0313] Preferred embodiments of the present invention relate to compounds of formula (I), wherein X is a bond and Y is a C1-C8 alkyl or C2-C8 alkenyl group, each bonded by a group selected from CO2R. e CONR b R h CONRe SO2R a The group is substituted with Z and is also replaced by 0 or 1 OR. d Substituents are used, or Y is a C2-C8 ynyl group; wherein Z is a 3-, 4-, 5-, or 6-member saturated or partially unsaturated monocyclic ring formed by 3-6 carbon atoms and 0 or 1 oxygen atom, wherein the ring is replaced by CO2R. e The group is substituted with 0 or 1 C1-C4 alkyl group, and R is wherein a R b R d R e or R h It has the meaning as defined herein, especially the meaning of preferred.

[0314] A more preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is a C1-C6 alkyl or C2-C6 alkenyl group, wherein the two groups mentioned later are surrounded by the group CO2R. e CONR b R h or CONR e SO2R a And it is substituted with 0 or 1 C1-C4 alkoxy group, and wherein R a R b R e or R h It has the meaning as defined herein, especially the meaning of preferred.

[0315] Particularly preferred embodiments relate to compounds of formula (I), wherein X is a bond and Y is a C1-C6 alkyl group, and is capped with a CO2R group. e CONR b R h or CONR e1 SO2R a And it is substituted with 0 or 1 C1-C4 alkoxy group, wherein R e1 It is hydrogen or C1-C4 alkyl, and wherein R is hydrogen or C1-C4 alkyl. a R b R e or R h It has the meaning as defined herein, especially the meaning of preferred.

[0316] Another preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is a C1-C6 alkyl group substituted by Z, wherein Z is a substituent group CO2R. e And it is a 3, 4, 5, or 6-membered saturated monocyclic carbon ring substituted with 0 or 1 C1-C4 alkyl group, or a 5 or 6-membered saturated monocyclic heterocycle containing 1 oxygen atom as a ring member, wherein the heterocycle is replaced by the CO2R group. e And it is substituted with 0 or 1 C1-C4 alkyl group, wherein R eIt has one of the meanings defined herein, and in particular one of the preferred meanings.

[0317] Another preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is a C2-C8 alkynyl group.

[0318] Another preferred embodiment relates to a compound of formula (I), wherein X is a bond, and R 10 -R 13 Independently hydrogen or methyl, preferably hydrogen, and Y is a C1-C6 alkyl group, which is surrounded by a CO2R group. e And it is substituted with 0 or 1 C1-C4 alkoxy group, and wherein R e It has one of the meanings defined herein, and in particular one of the preferred meanings.

[0319] A more preferred embodiment relates to a compound of formula (I), wherein X is a bond, and R 10 -R 13 Independently hydrogen, and Y is a C1-C4 alkyl group, which is surrounded by the CO2R group. e Replace, where R e It has one of the meanings defined herein, and in particular one of the preferred meanings.

[0320] Another preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is Z, which is 3, 4, 5, 6, 7 or 8-membered saturated, partially unsaturated or aromatic monocyclic, bicyclic, spirocyclic or polycyclic, formed by r carbon atoms, n oxygen atoms, n sulfur atoms and k nitrogen atoms, each separated by m atoms selected from CO2R e CONR b R h CONR e SO2R a R b R c R e and R f The group is substituted, wherein R is a group that is substituted for R. a R b R c R e or R h It has the meaning as defined herein, especially the meaning of preferred.

[0321] A more preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is Z, which is a 3, 4, 5, 6, 7 or 8-membered saturated or partially unsaturated monocyclic carbon ring, and is bound by a CO2R group. e It is substituted with 0 or 1 fluorine atom and 0 or 1 C1-C4 alkyl group, wherein R e It has one of the meanings defined herein, and in particular one of the preferred meanings.

[0322] Particularly preferred embodiments relate to compounds of formula (I), wherein X is a bond and Y is Z, which is a 4, 5, 6, 7 or 8-membered saturated or partially unsaturated monocyclic carbon ring, and is surrounded by a CO2R group. e And it is replaced by 0 or 1 fluorine atom, where R e It has one of the meanings defined herein, and particularly one of the preferred meanings. Specifically, Z is a 4, 5, 6, or 7-membered saturated or partially unsaturated monocyclic carbon ring, surrounded by the CO2R group. e And it is replaced by 0 or 1 fluorine atom, where R e It has one of the meanings defined herein, and in particular one of the preferred meanings.

[0323] Another preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is Z, which is a 5, 6, 7 or 8-membered saturated or partially unsaturated monocyclic carbon ring, which is bonded by a CO2R group. e And is substituted with 0 or 1 C1-C4 alkyl group, wherein R e It has one of the meanings defined herein, and in particular one of the preferred meanings.

[0324] Another particularly preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is Z, which is a 6, 7, or 8-membered saturated or partially unsaturated monocyclic carbon ring, and is bound by a CO2R group. e And is substituted with 0 or 1 C1-C4 alkyl group, wherein R e It has one of the meanings defined herein, and particularly one of the preferred meanings. Specifically, Z is a 6- or 7-membered saturated bicyclic (spirocyclic or bridged) carbon ring surrounded by the CO2R group. e Replace, where R e It has one of the meanings defined herein, and in particular one of the preferred meanings.

[0325] Another preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is Z, which is an 8-membered saturated polycyclic carbocyclic ring, and is bonded by a CO2R group. e And is substituted with 0 or 1 C1-C4 alkyl group, wherein R e It has one of the meanings defined herein, and particularly one of the preferred meanings. Specifically, Z represents the substituent group CO2R. e Substituted cubic alkyl, wherein R e It has one of the meanings defined herein, and in particular one of the preferred meanings.

[0326] Another preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is Z, which is a 5- or 6-member saturated or partially unsaturated monocyclic heterocycle containing one oxygen atom or one sulfur atom as a ring member, wherein the heterocycle is bounded by a CO2R group. e And it is substituted with 0 or 1 C1-C4 alkyl group, wherein R eIt has one of the meanings defined herein, and in particular one of the preferred meanings.

[0327] Particularly preferred embodiments relate to compounds of formula (I), wherein X is a bond and Y is Z, which is a 5- or 6-member saturated or partially unsaturated monocyclic heterocycle containing one oxygen atom or one sulfur atom as a ring member, wherein the heterocycle is bounded by a CO2R group. e Replace, and where R e It has one of the meanings defined herein, and in particular one of the preferred meanings.

[0328] Another preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is Z, which is a 5- or 6-membered heteroaromatic ring containing 1, 2, 3 or 4 heteroatoms selected from N, O and S as ring members, wherein the heteroaromatic ring is substituted with 0 or 1 C1-C4 alkyl group.

[0329] A particularly preferred embodiment relates to a compound of formula (I), wherein X is a bond and Y is Z, which is a 5-membered heteroaromatic ring containing 1, 2, 3 or 4 N atoms as ring members, wherein the heteroaromatic ring is substituted with 0 or 1 C1-C4 alkyl group.

[0330] R e Preferably, the group is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, and C2-C4 alkynyl, wherein the latter six groups are substituted by m groups selected from: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfonyl, phenylsulfinyl, phenylthio, and furanyl. The C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfonyl, phenylsulfinyl, and phenylthio groups may be substituted by 0, 1, 2, 3, 4, or 5 fluorine, chlorine, and / or bromine atoms. More preferably, R e It is hydrogen, C1-C6 alkyl, which is unsubstituted or substituted with 1, 2 or 3 fluorine or chlorine atoms or with 1 group selected from C1-C2 alkoxy, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfonyl, phenylthio and furanyl; or it is C2-C4 ynyl or C3-C6 cycloalkyl-C1-C3 alkyl.

[0331] The preferred compounds of the present invention are those of formula (I), wherein the substituents have the following meanings:

[0332] R 1It is hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, preferably hydrogen, C1-C3 alkyl or C3-C4 cycloalkyl, more preferably hydrogen;

[0333] R 2 It is hydrogen;

[0334] R 3 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0335] R 4 It can be hydrogen or fluorine, with hydrogen being preferred;

[0336] R 5 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0337] R 6 It is hydrogen;

[0338] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NCOR d The unit, wherein one carbon atom has p oxo groups, and wherein the ring is bounded by n R groups. g replace;

[0339] R 9 It is hydrogen;

[0340] X is the key;

[0341] Y is Z;

[0342] Z is a 3, 4, 5, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring, excluding phenyl groups, and is formed by r carbon atoms, k nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0343] R aEach is independently a C1-C6 alkyl or C3-C6 cycloalkyl group, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, C1-C3 alkoxy;

[0344] R b Each is independently hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl, and each is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0345] R c Each can be independently classified as fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, or S(O). n R a Or C1-C6 alkoxy, C3-C6 alkenoxy, or C3-C6 alkynoxy, wherein the aliphatic portion of each of the three groups mentioned later is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, and C1-C2 alkoxy.

[0346] R d Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0347] R e Each has its own R d One of the given meanings;

[0348] R f Each is independently a C1-C3 alkyl or C1-C3 alkoxy;

[0349] R g Each of these groups can be independently halogen, nitro, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0350] R h Each of the six groups is independently hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0351] r is 1, 2, 3, 4, 5, or 6;

[0352] k is 0, 1, or 2;

[0353] n can be 0, 1, or 2 independently;

[0354] m can be 0, 1, 2, 3, 4 or 5 independently;

[0355] p is 0 or 1;

[0356] q is 1, 2, 3, 4, 5, 6, or 7;

[0357] u is 0, 1, or 2;

[0358] w is 0, 1, or 2;

[0359] x is 0, 1, or 2;

[0360] v can be 0, 1, 2, or 3;

[0361] The condition is that at least one of u, v, w, and x is not 0.

[0362] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0363] R 1 It is hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, preferably hydrogen, C1-C3 alkyl or C3-C4 cycloalkyl, more preferably hydrogen;

[0364] R 2 It is hydrogen;

[0365] R 3 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0366] R 4 It can be hydrogen or fluorine, with hydrogen being preferred;

[0367] R 5 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0368] R 6 It is hydrogen;

[0369] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR.d and NCOR d The unit, wherein one carbon atom has p oxo groups, and wherein the ring is bounded by n R groups. g replace;

[0370] R 9 It is hydrogen;

[0371] X is the key;

[0372] Y is Z;

[0373] Z is a 3, 4, 5, or 6-member saturated, partially unsaturated, completely unsaturated, or aromatic ring, excluding phenyl groups. It is formed by r carbon atoms, k nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is surrounded by m atoms selected from CO2R. e The groups are substituted, and the sulfur atom and the carbon atom are equipped with n oxo groups;

[0374] R d Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0375] R e Each has its own R d One of the given meanings;

[0376] R g Each of these groups can be independently halogen, nitro, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0377] r is 1, 2, 3, 4, 5, or 6;

[0378] k is 0, 1, or 2;

[0379] n can be 0, 1, or 2 independently;

[0380] m can be 0, 1, 2, 3, 4 or 5 independently;

[0381] p is 0 or 1;

[0382] q is 1, 2, 3, 4, 5, 6, or 7;

[0383] u is 0, 1, or 2;

[0384] w is 0, 1, or 2;

[0385] x is 0, 1, or 2;

[0386] v can be 0, 1, 2, or 3;

[0387] The condition is that at least one of u, v, w, and x is not 0.

[0388] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0389] R 1 It is hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, preferably hydrogen, C1-C3 alkyl or C3-C4 cycloalkyl, more preferably hydrogen;

[0390] R 2 It is hydrogen;

[0391] R 3 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0392] R 4 It can be hydrogen or halogen, preferably hydrogen;

[0393] R 5 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0394] R 6 It is hydrogen;

[0395] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NCOR d The unit, wherein one carbon atom has p oxo groups, and wherein the ring is bounded by n R groups. g replace;

[0396] R 9 It is hydrogen;

[0397] X is the key;

[0398] Y is Z;

[0399] Z is a 5-membered saturated, partially unsaturated, or fully unsaturated carbon ring, which is substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f ;

[0400] R a Each is independently a C1-C6 alkyl, C2-C4 alkynyl or C3-C6 cycloalkyl group, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, C1-C3 alkoxy.

[0401] R b Each is independently hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl, and each is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0402] R c Each can be independently classified as fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, or S(O). n R a Or C1-C6 alkoxy, C3-C6 alkenoxy, or C3-C6 alkynoxy, wherein the aliphatic portion of each of the three groups mentioned later is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, and C1-C2 alkoxy.

[0403] R d Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0404] R e Each has its own R d One of the given meanings;

[0405] R f Each is independently a C1-C3 alkyl or C1-C3 alkoxy;

[0406] R gEach of these groups can be independently halogen, nitro, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0407] R h Each of the six groups is independently hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0408] m can be 0, 1, 2 or 3 independently;

[0409] n can be 0, 1, or 2 independently;

[0410] p is 0 or 1;

[0411] q is 1, 2, 3, 4, 5, 6, or 7;

[0412] u is 0, 1, or 2;

[0413] w is 0, 1, or 2;

[0414] x is 0, 1, or 2;

[0415] v can be 0, 1, 2, or 3;

[0416] The condition is that at least one of u, v, w, and x is not 0.

[0417] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0418] R 1 It is hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, preferably hydrogen, C1-C3 alkyl or C3-C4 cycloalkyl, more preferably hydrogen;

[0419] R 2 It is hydrogen;

[0420] R 3 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0421] R4 It can be hydrogen or fluorine, with hydrogen being preferred;

[0422] R 5 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0423] R 6 It is hydrogen;

[0424] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NCOR d The unit, wherein one carbon atom has p oxo groups, and wherein the ring is bounded by n R groups. g replace;

[0425] R 9 It is hydrogen;

[0426] X is the key;

[0427] Y is Z;

[0428] Z is a 5-member saturated, partially unsaturated, or fully unsaturated carbon ring, with m members selected from CO2R. e and R b Substitution of groups;

[0429] R b Each is independently hydrogen or C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0430] R d Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0431] R e Each has its own R d One of the given meanings;

[0432] R gEach of these groups can be independently halogen, nitro, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0433] m can be 0, 1, or 2 independently;

[0434] n can be 0, 1, or 2 independently;

[0435] p is 0 or 1;

[0436] q is 1, 2, 3, 4, 5, 6, or 7;

[0437] u is 0, 1, or 2;

[0438] w is 0, 1, or 2;

[0439] x is 0, 1, or 2;

[0440] v can be 0, 1, 2, or 3;

[0441] The condition is that at least one of u, v, w, and x is not 0.

[0442] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0443] R 1 It is hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, preferably hydrogen, C1-C3 alkyl or C3-C4 cycloalkyl, more preferably hydrogen;

[0444] R 2 It is hydrogen;

[0445] R 3 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0446] R 4 It can be hydrogen or fluorine, with hydrogen being preferred;

[0447] R 5 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0448] R 6 It is hydrogen;

[0449] R7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NCOR d The unit, wherein one carbon atom has p oxo groups, and wherein the ring is bounded by n R groups. g replace;

[0450] R 9 It is hydrogen;

[0451] X is the key;

[0452] Y is a C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, or C2-C8 alkynyl, and each of the groups is surrounded by m elements selected from fluorine and CO2R. e Substitution of groups;

[0453] R d Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0454] R e Each has its own R d One of the given meanings;

[0455] R g Each of these groups can be independently halogen, nitro, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0456] m can be 0, 1, or 2 independently;

[0457] n can be 0, 1, or 2 independently;

[0458] p is 0 or 1;

[0459] q is 1, 2, 3, 4, 5, 6, or 7;

[0460] u is 0, 1, or 2;

[0461] w is 0, 1, or 2;

[0462] x is 0, 1, or 2;

[0463] v can be 0, 1, 2, or 3;

[0464] The condition is that at least one of u, v, w, and x is not 0.

[0465] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0466] R 1 It is hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 alkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy, preferably hydrogen, C1-C3 alkyl or C3-C4 cycloalkyl, more preferably hydrogen;

[0467] R 2 It is hydrogen;

[0468] R 3 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0469] R 4 It can be hydrogen or fluorine, with hydrogen being preferred;

[0470] R 5 It is halogen, cyano, C1-C3 alkyl, preferably fluorine or chlorine;

[0471] R 6 It is hydrogen;

[0472] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NCOR d The unit, wherein one carbon atom has p oxo groups, and wherein the ring is bounded by n R groups. g replace;

[0473] R 9 It is hydrogen;

[0474] X is the key;

[0475] Y is a C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, or C2-C8 alkynyl group, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d, Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e ;

[0476] Z is a 3, 4, 5, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring, excluding phenyl groups, and is formed by r carbon atoms, k nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0477] R a Each is independently a C1-C6 alkyl or C3-C6 cycloalkyl group, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0478] R bEach is independently hydrogen, C1-C6 alkyl or C3-C6 cycloalkyl, and each is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0479] R c Each can be independently classified as fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, or S(O). n R a Or C1-C6 alkoxy, C3-C6 alkenoxy, or C3-C6 alkynoxy, wherein the aliphatic portion of each of the three groups mentioned later is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, and C1-C2 alkoxy.

[0480] R d Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0481] R e Each has its own R d One of the given meanings;

[0482] R f Each is independently a C1-C3 alkyl or C1-C3 alkoxy;

[0483] R g Each of these groups can be independently halogen, nitro, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0484] R h Each of the six groups is independently hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0485] r is 1, 2, 3, 4, 5, or 6;

[0486] k is 0, 1, or 2;

[0487] n can be 0, 1, or 2 independently;

[0488] m can be 0, 1, 2, 3, 4 or 5 independently;

[0489] p is 0 or 1;

[0490] q is 1, 2, 3, 4, 5, 6, or 7;

[0491] u is 0, 1, or 2;

[0492] w is 0, 1, or 2;

[0493] x is 0, 1, or 2;

[0494] v can be 0, 1, 2, or 3;

[0495] The condition is that at least one of u, v, w, and x is not 0.

[0496] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0497] R 1 It can be hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0498] R 2 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0499] R 3 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0500] R 4 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, or C2-C3 haloalkynyl.

[0501] R 5It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0502] R 6 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0503] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 4- or 5-membered monocyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, and x atoms selected from NR. d The unit, wherein the ring is bounded by n groups R g replace;

[0504] R 9 It can be hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C3 alkoxy-C1-C3 alkoxy.

[0505] X is the key (X 0 () or selected from the following divalent units: (X) 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ) and (X 6 ):

[0506]

[0507] R 10 -R 15 Each of these can be independently represented as hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyanide, or CO2R. e CONR b R d R aOr C1-C6 alkyl, C3-C5 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, hydroxyl and cyano; or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenyloxy or C3-C6 alkynyloxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and C1-C2 alkoxy;

[0508] Y represents hydrogen, cyano, hydroxyl, or Z.

[0509] Or C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 The alkynyl group is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e ;

[0510] Z is a 3, 4, 5, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring, excluding phenyl groups, and is formed by r carbon atoms, k nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2Re CONR b R h S(O) n R a SO2NR b R d SO2NR b COR e COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e R b R c R e and R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0511] R a Each is independently a C1-C6 alkyl or C3-C6 cycloalkyl group, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0512] R b Each is independently hydrogen or has a relationship with R a One of the given meanings;

[0513] R c Each of these groups represents one of the following: fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, or S(O). n R a Or C1-C6 alkoxy, C3-C6 alkenoxy, or C3-C6 alkynoxy, wherein the aliphatic portion of each of the three groups mentioned later is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, and C1-C2 alkoxy.

[0514] Rd Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0515] R e Each has its own R d One of the given meanings;

[0516] R f Each is independently a C1-C3 alkyl or C1-C3 alkoxy;

[0517] R g Each of these groups can be independently halogenated, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0518] R h It is independently hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0519] k is 0, 1, or 2;

[0520] m can be 0, 1, 2, 3, 4 or 5 independently;

[0521] n can be 0, 1, or 2 independently;

[0522] q is 2 or 3;

[0523] r is 1, 2, 3, 4, 5, or 6;

[0524] x is 0 or 1;

[0525] u is 0 or 1;

[0526] The condition is that the sum of u and x is preferably 1 or 2.

[0527] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0528] R 1 It can be hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0529] R 2 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0530] R 3 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0531] R 4 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, or C2-C3 haloalkynyl.

[0532] R 5 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0533] R 6 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0534] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 4- or 5-membered monocyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, and x atoms selected from NR. d The unit, wherein the ring is bounded by n groups Rg replace;

[0535] R 9 It can be hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C3 alkoxy-C1-C3 alkoxy.

[0536] X is the key;

[0537] Y is Z, or C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, or C2-C8 alkynyl, each substituted by m groups selected from: fluorine, chlorine, bromine, iodine, hydroxyl, and cyano; or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenyloxy, or C3-C6 alkynyl, each substituted by m groups selected from fluorine, chlorine, bromine, iodine, hydroxyl, and cyano; or C1-C6 alkoxy, C3-C6 cycloalkoxy, C3-C6 alkenyloxy, or C3-C6 alkynyloxy, each substituted by m groups selected from fluorine, chlorine, bromine, iodine, hydroxyl, and cyano; CONR e SO2R a and CO2R e Substitution of groups;

[0538] Z is a 4-5 member saturated or partially unsaturated ring, formed by r carbon atoms and n oxygen atoms, and substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f ;

[0539] R a Each is independently a C1-C6 alkyl or C3-C6 cycloalkyl group, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0540] R b Each is independently hydrogen or C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0541] R c Each can be independently classified as fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, or S(O). n R a Or C1-C6 alkoxy, C3-C6 alkenoxy, or C3-C6 alkynoxy, wherein the aliphatic portion of each of the three groups mentioned later is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, and C1-C2 alkoxy.

[0542] R d Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0543] R e Each has its own R d One of the given meanings;

[0544] R f Each is independently a C1-C3 alkyl or C1-C3 alkoxy;

[0545] R g Each of these groups can be independently halogenated, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0546] R h Each of the six groups is independently hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0547] m can be 0, 1, 2, 3, 4 or 5 independently;

[0548] n can be 0, 1, or 2 independently;

[0549] q is 2 or 3;

[0550] r is 1, 2, 3, 4, 5, or 6;

[0551] x is 0 or 1;

[0552] u is 0 or 1;

[0553] The condition is that the sum of u and x is preferably 1 or 2.

[0554] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0555] R1 It can be hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0556] R 2 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0557] R 3 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0558] R 4 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, or C2-C3 haloalkynyl.

[0559] R 5 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0560] R 6 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0561] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 4- or 5-membered monocyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, and x atoms selected from NR. d The unit, wherein the ring is bounded by n groups R greplace;

[0562] R 9 It can be hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C3 alkoxy-C1-C3 alkoxy.

[0563] X is the key;

[0564] Y is Z;

[0565] Z is a 4-5 member saturated or partially unsaturated ring, formed by r carbon atoms and n oxygen atoms, and substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f ;

[0566] R a Each is independently a C1-C6 alkyl or C3-C6 cycloalkyl group, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0567] R b Each is independently hydrogen or C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0568] R c Each can be independently classified as fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, or S(O). n R a Or C1-C6 alkoxy, C3-C6 alkenoxy, or C3-C6 alkynoxy, wherein the aliphatic portion of each of the three groups mentioned later is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, and C1-C2 alkoxy.

[0569] R d Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0570] Re Each has its own R d One of the given meanings;

[0571] R f Each is independently a C1-C3 alkyl or C1-C3 alkoxy;

[0572] R g Each of these groups can be independently halogenated, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0573] R h Each of the six groups is independently hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0574] m can be 0, 1, 2, 3, 4 or 5 independently;

[0575] n can be 0, 1, or 2 independently;

[0576] q is 2 or 3;

[0577] r is 1, 2, 3, 4, 5, or 6;

[0578] x is 0 or 1;

[0579] u is 0 or 1;

[0580] The condition is that the sum of u and x is preferably 1 or 2.

[0581] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0582] R 1 It can be hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0583] R 2It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0584] R 3 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0585] R 4 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, or C2-C3 haloalkynyl.

[0586] R 5 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl;

[0587] R 6 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy.

[0588] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 4- or 5-membered monocyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, and x atoms selected from NR. d The unit, wherein the ring is bounded by n groups R g replace;

[0589] R 9It can be hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C3 alkoxy-C1-C3 alkoxy.

[0590] X is the key;

[0591] Y is C1-C 12 Alkyl, C3-C8 cycloalkyl, C2-C 12 Alkenyl or C2-C 12 The alkynyl group is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a SO2NR b R d SO2NR b COR e CO2R e CONR b R h COR b CONR e SO2R a NR b R e NR b COR e NR b CONR e R e NR b CO2R e NR b SO2R e NR b SO2NR b R e OCONR b R e OCSNR b R e POR f R f and C(R) b ) = NOR e ;

[0592] Z is a 3, 4, 5, or 6-membered saturated, partially unsaturated, fully unsaturated, or aromatic ring, excluding phenyl groups, and is formed by r carbon atoms, k nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is substituted by m groups selected from the following: CO2R e CONR b Rh CONR e SO2R a R b R c R e and R f Furthermore, the sulfur and carbon atoms in this structure have n oxy groups;

[0593] R a Each is independently a C1-C6 alkyl or C3-C6 cycloalkyl group, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0594] R b Each is independently hydrogen or has a relationship with R a One of the given meanings;

[0595] R c Each can be independently classified as fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, or S(O). n R a Or C1-C6 alkoxy, C3-C6 alkenoxy, or C3-C6 alkynoxy, wherein the aliphatic portion of each of the three groups mentioned later is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, and C1-C2 alkoxy.

[0596] R d Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0597] R e Each has its own R d One of the given meanings;

[0598] R f Each is independently a C1-C3 alkyl or C1-C3 alkoxy;

[0599] R g Each of these groups represents a halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl, and C1-C3 alkylsulfonyl.

[0600] R h Each of the six groups is independently hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, wherein each of the latter six groups is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0601] k is 0, 1, or 2;

[0602] m can be 0, 1, 2, 3, 4 or 5 independently;

[0603] n can be 0, 1, or 2 independently;

[0604] q is 2 or 3;

[0605] r is 1, 2, 3, 4, 5, or 6;

[0606] x is 0 or 1;

[0607] u is 0 or 1;

[0608] The condition is that the sum of u and x is preferably 1 or 2.

[0609] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0610] R 1 It is hydrogen;

[0611] R 2 It is hydrogen;

[0612] R 3 It is a halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

[0613] R 4 It can be hydrogen or halogen, preferably hydrogen;

[0614] R 5 It is a halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl or C1-C3 haloalkoxy, preferably fluorine or chlorine;

[0615] R 6 It is hydrogen;

[0616] R 7 and R 8 Together with the carbon atoms they are bonded to, they form a saturated or partially unsaturated 4 or 5-membered monocyclic or bicyclic heterocycle W, which, in addition to the carbon atom, contains q carbon atoms and u oxygen atoms, wherein the ring is bounded by n groups R. g replace;

[0617] R 9It is hydrogen;

[0618] X is the key;

[0619] Y is Z;

[0620] Z is a 3, 4, 5, or 6-member saturated, partially unsaturated, completely unsaturated, or aromatic ring, excluding phenyl groups. It is formed by r carbon atoms, k nitrogen atoms, n sulfur atoms, and n oxygen atoms, and is surrounded by m atoms selected from CO2R. e The groups are substituted, and the sulfur atom and the carbon atom are equipped with n oxo groups;

[0621] R e Each of the following groups is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, wherein each of the last five groups is substituted by m groups selected from the following groups: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl and C1-C3 alkylthio;

[0622] R g Each of these groups can be independently halogen, nitro, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0623] r is 1, 2, 3, 4, 5, or 6;

[0624] k can be 0, 1, 2, 3 or 4;

[0625] n can be 0, 1, or 2 independently;

[0626] m can be 0, 1, 2, 3, 4 or 5 independently;

[0627] q is 2 or 3;

[0628] u is 1.

[0629] Other preferred compounds of the present invention are compounds of formula (I), wherein the substituents have the following meanings:

[0630] R 1It can be hydrogen, C1-C3 alkyl, C3-C4 cycloalkyl, C1-C3 haloalkyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0631] R 2 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0632] R 3 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0633] R 4 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 halocycloalkyl, C1-C3 haloalkoxy, C2-C3 haloalkenyl, or C2-C3 haloalkynyl.

[0634] R 5 It can be hydrogen, halogen, nitro, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl;

[0635] R 6 It can be hydrogen, halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0636] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 4-8 member monocyclic or bicyclic heterocycles W, which, in addition to the carbon atom, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NC(O)OR dThe unit, wherein one carbon atom has p oxo groups, and wherein the ring is bounded by n R groups. g replace;

[0637] R 9 It can be hydrogen, C1-C6 alkyl, C3-C4 cycloalkyl, C1-C6 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalynyl, C1-C6 alkoxy, C1-C6 haloalkoxy or C1-C3 alkoxy-C1-C3 alkoxy;

[0638] X is a key or X 6 ;where R 10 -R 13 Independently hydrogen or methyl;

[0639] Y is Z, or a C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, or C2-C8 ynyl group, each of which is substituted by m groups selected from the following: fluorine, OR d Z, CONR e SO2R a CONR b R h and CO2R e ;

[0640] Z is a 3-8 member saturated or partially unsaturated monocyclic, bicyclic, spirocyclic, or polycyclic ring, formed by r carbon atoms, n oxygen atoms, n sulfur atoms, and k nitrogen atoms, and substituted by m groups selected from the following: CO2R e CONR b R h CONR e SO2R a R b R c R e and R f ;

[0641] R a It is a C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0642] R b It is hydrogen or C1-C6 alkyl or C3-C6 cycloalkyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, iodine, cyano and hydroxyl;

[0643] R c The groups are fluorine, chlorine, bromine, iodine, cyanide, hydroxyl, and S(O). n R aOr C1-C6 alkoxy, C3-C6 alkenoxy or C3-C6 alkynoxy, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0644] R d Each is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl, or C2-C4 ynyl, each substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, COOR a C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, and C1-C3 alkylthio;

[0645] R e Each of them is independently hydrogen or C1-C6 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, phenyl-C1-C3 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano, C1-C2 alkoxy, C1-C3 alkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfonyl, phenylsulfinyl, phenylthio and furanyl;

[0646] R f It is a C1-C3 alkyl or C1-C3 alkoxy;

[0647] R g Halogen, nitro, hydroxy, cyano, C1-C3 alkyl, C1-C3 haloalkyl, hydroxy-C1-C3 alkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, hydroxy-C3-C5 cycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkoxycarbonyl, C2-C3 alkenyl, C2-C3 haloalkenyl, C2-C3 alkynyl, C2-C3 haloalkynyl, C1-C3 alkylthio, C1-C3 alkylsulfinyl or C1-C3 alkylsulfonyl; or two Rs bonded to the same carbon atom g Together they form a methylene group (=CH2);

[0648] R h It is hydrogen or C1-C6 alkyl, C1-C2 alkoxy, C3-C6 cycloalkyl, C2-C4 alkenyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl or C2-C4 alkynyl, each of which is substituted by m groups selected from the following: fluorine, chlorine, bromine, cyano and C1-C2 alkoxy;

[0649] k can be 0, 1, 2, 3 or 4;

[0650] m can be 0, 1, 2, 3, 4, or 5;

[0651] n can be 0, 1, 2, 3, or 4;

[0652] p is 0 or 1;

[0653] q is 2, 3, 4, 5, or 6;

[0654] r is 1, 2, 3, 4, 5, 6, 7 or 8;

[0655] u is 0, 1, or 2;

[0656] v is 0 or 1;

[0657] w is 0 or 1;

[0658] x is 0 or 1;

[0659] The condition is that at least one of u, v, w, and x is not 0.

[0660] However, the preferred compound is of formula (I), wherein the substituents have the following meanings:

[0661] R 1 It is hydrogen;

[0662] R 2 It is hydrogen or halogen;

[0663] R 3 It can be hydrogen, halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0664] R 4 It is hydrogen or halogen;

[0665] R 5 It can be hydrogen, halogen, cyano, C1-C3 alkyl or C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy;

[0666] R 6 It is hydrogen;

[0667] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3, 4, 5, or 6-membered monocyclic heterocycles W or 6, 7, or 8-membered bicyclic (preferably bridging) heterocycles W, which, in addition to the carbon atoms, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NC(O)OR d The unit, wherein one carbon atom has p oxo groups, and wherein the ring is bounded by n R groups. g replace;

[0668] R 9 It is hydrogen or C1-C4 alkyl;

[0669] X is the bond and Y is Z, where

[0670] Z is a 3, 4, 5, 6, 7, or 8-membered saturated or partially unsaturated monocyclic carbon ring, surrounded by the CO2R group. e It is substituted with 0 or 1 fluorine atom and 0 or 1 C1-C4 alkyl group; or

[0671] Z is a 6, 7, or 8-membered saturated or partially unsaturated bicyclic carbon ring, surrounded by the CO2R group. e And substituted with 0 or 1 C1-C4 alkyl group; or

[0672] Z is an 8-membered saturated polycyclic carbon ring, surrounded by the CO2R group. e And substituted with 0 or 1 C1-C4 alkyl group; or

[0673] Z is a 5- or 6-membered saturated or partially unsaturated monocyclic heterocycle containing one oxygen atom or one sulfur atom as a ring member, wherein the heterocycle is bound by the CO2R group. e And substituted with 0 or 1 C1-C4 alkyl group; or

[0674] Z is a 5- or 6-membered heteroaromatic ring containing 1, 2, 3, or 4 heteroatoms selected from N, O, and S as ring members, wherein the heteroaromatic ring is substituted by 0 or 1 C1-C4 alkyl group; or

[0675] X is a bond and Y is a C1-C6 alkyl or C2-C6 alkenyl group, wherein the two groups mentioned later are bound by the group CO2R. e CONR b R h or CONR e SO2R a And substituted with 0 or 1 C1-C4 alkyl group; or

[0676] X is a bond and Y is a C1-C6 alkyl group substituted by Z, where Z is a 3, 4, 5, or 6-membered saturated monocyclic carbon ring, and its substituted group is CO2R. e It is either substituted with 0 or 1 C1-C4 alkyl group, or is a 5 or 6-membered saturated monocyclic heterocycle containing 1 oxygen atom as a ring member, wherein the heterocycle is replaced by the CO2R group. e And substituted with 0 or 1 C1-C4 alkyl group; or

[0677] X is a bond and Y is a C2-C8 ynyl group; or

[0678] X is X 6 , where R 10 -R 13 Independently hydrogen or methyl, preferably hydrogen; and Y is a substituent CO2R. e And C1-C6 alkyl groups substituted with 0 or 1 C1-C4 alkoxy groups;

[0679] Ra It is a C1-C6 alkyl group;

[0680] R b It is hydrogen or C1-C6 alkyl;

[0681] R d Each is independently hydrogen or C1-C6 alkyl;

[0682] R e Each is independently hydrogen, C1-C6 alkyl, substituted with 0, 1, 2 or 3 fluorine or chlorine atoms or with 0 or 1 group selected from C1-C2 alkoxy, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylthio, phenylsulfonyl and furanyl; wherein the aliphatic or aromatic moiety of the C1-C2 alkoxy, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylthio and phenylsulfonyl groups may have 0, 1, 2, 3, 4 or 5 fluorine, chlorine and / or bromine atoms (but especially unsubstituted); or R e It is C2-C4 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C3 alkyl;

[0683] R g It is a C1-C3 alkyl or C1-C3 haloalkyl; or two R atoms bonded to the same carbon atom. g Together they form a methylene group (=CH2);

[0684] R h It is hydrogen, a C1-C6 alkyl group substituted with 0 or 1 cyano group; or a C2-C4 alkynyl group;

[0685] n is 0, 1, or 2;

[0686] p is 0 or 1;

[0687] q can be 1, 2, 3, 4, 5, or 6;

[0688] u is 0, 1, or 2;

[0689] v is 0 or 1;

[0690] w is 0 or 1;

[0691] x is 0 or 1;

[0692] The condition is that the sum of u, v, w, and x is 1 or 2.

[0693] In particular, in compounds of formula (I), the substituents have the following meanings:

[0694] R 1 It is hydrogen;

[0695] R 2 It is hydrogen;

[0696] R 3 It is a halogen, cyano, or C1-C3 haloalkoxy group;

[0697] R 4 It is hydrogen or halogen;

[0698] R 5 It is hydrogen or halogen;

[0699] R 6 It is hydrogen;

[0700] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3, 4, 5, or 6-membered monocyclic heterocycles W or 6, 7, or 8-membered bicyclic (preferably bridging) heterocycles W, which, in addition to the carbon atoms, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NC(O)OR d The unit, wherein the ring is bounded by n groups R g replace;

[0701] R 9 It is hydrogen;

[0702] X is the bond and Y is Z, where

[0703] Z is a 4, 5, 6, 7, or 8-membered saturated or partially unsaturated monocyclic carbon ring, surrounded by the CO2R group. e And replaced by 0 or 1 fluorine atom; or

[0704] Z is a 5, 6, 7, or 8-membered saturated or partially unsaturated bicyclic (preferably spirocyclic or bridged) carbon ring, surrounded by the CO2R group. e And substituted with 0 or 1 C1-C4 alkyl group; or

[0705] Z is a 5- or 6-membered saturated or partially unsaturated monocyclic heterocycle containing one oxygen atom or one sulfur atom as a ring member, wherein the heterocycle is bound by the CO2R group. e Replace; or

[0706] Z is a 5-membered heteroaromatic ring containing 1, 2, 3, or 4 nitrogen atoms as ring members, wherein the heteroaromatic ring is substituted by 0 or 1 C1-C4 alkyl group; or

[0707] X is a bond and Y is a C1-C6 alkyl group, with a CO2R group as the bond. e CONR b R h or CONR e1 SO2R a And it is substituted with 0 or 1 C1-C4 alkoxy group; or

[0708] X is a bond and Y is a C1-C6 alkyl or C2-C8 ynyl; or

[0709] X is X 6 , where R 10 -R 13 Independently hydrogen; and Y is a group with CO2R e Substituted C1-C4 alkyl groups;

[0710] R a It is a C1-C6 alkyl group;

[0711] R b It is hydrogen;

[0712] R d Each is independently hydrogen or C1-C6 alkyl;

[0713] R e1 It is hydrogen or C1-C4 alkyl;

[0714] R e Each is independently hydrogen, C1-C6 alkyl, which is substituted with 0, 1, 2 or 3 fluorine and / or chlorine atoms or with 0 or 1 group selected from C1-C2 alkoxy, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfonyl, phenylthio and furanyl; wherein the aliphatic or aromatic structural part of C1-C2 alkoxy, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfonyl and phenylthio may have 0, 1, 2, 3, 4 or 5 fluorine, chlorine and / or bromine atoms (but especially unsubstituted); or is C2-C4 alkynyl or C3-C6 cycloalkyl-C1-C3 alkyl;

[0715] R g It is a C1-C3 alkyl group; or two R atoms bonded to the same carbon atom. g Together they form a methylene group (=CH2);

[0716] R h It is a C1-C6 alkyl group substituted with 0 or 1 cyano group; or a C2-C4 alkynyl group;

[0717] n is 0, 1, or 2;

[0718] q can be 1, 2, 3, 4, 5, or 6;

[0719] u is 0, 1, or 2;

[0720] v is 0 or 1;

[0721] w is 0 or 1;

[0722] x is 0 or 1;

[0723] The condition is that the sum of u, v, w, and x is 1 or 2.

[0724] In particular, in compounds of formula (I), the substituents have the following meanings:

[0725] R 1 It is hydrogen;

[0726] R 2 It is hydrogen;

[0727] R 3 It is a halogen, cyano, or C1-C3 haloalkoxy group;

[0728] R 4 It is hydrogen or halogen;

[0729] R 5 It is hydrogen or halogen;

[0730] R 6 It is hydrogen;

[0731] R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3, 4, 5, or 6-membered monocyclic heterocycles W or 6, 7, or 8-membered bicyclic (preferably bridging) heterocycles W, which, in addition to the carbon atoms, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NC(O)OR d The unit, wherein the ring is bounded by n groups R g replace;

[0732] R 9 It is hydrogen;

[0733] X is the bond and Y is Z, where

[0734] Z is a 4, 5, 6, or 7-membered saturated or partially unsaturated monocyclic carbon ring, surrounded by the CO2R group. e And replaced by 0 or 1 fluorine atom; or

[0735] Z is a 6- or 7-membered saturated bicyclic (preferably spirocyclic or bridged) carbon ring, surrounded by the CO2R group. e Replace; or

[0736] Z is a 5-membered saturated or partially unsaturated monocyclic heterocycle containing one oxygen atom or one sulfur atom as a ring member, wherein the heterocycle is bound by the CO2R group. e Replace; or

[0737] Z is a 5-membered heteroaromatic ring containing 1, 2, 3, or 4 nitrogen atoms as ring members, wherein the heteroaromatic ring is substituted by 0 or 1 C1-C4 alkyl group; or

[0738] X is a bond and Y is a C1-C6 alkyl group, with a CO2R group as the bond. eCONR b R h or CONR e1 SO2R a And it is substituted by one C1-C4 alkoxy group; or

[0739] X is a bond and Y is a C2-C8 ynyl group; or

[0740] X is X 6 , where R 10 -R 13 Independently hydrogen; and Y is a group with CO2R e Substituted C1-C4 alkyl groups;

[0741] R a It is a C1-C6 alkyl group;

[0742] R b It is hydrogen;

[0743] R d Each is independently hydrogen or C1-C6 alkyl;

[0744] R e1 It is hydrogen or C1-C4 alkyl;

[0745] R e Each is independently hydrogen, C1-C6 alkyl, which is substituted with 0, 1, 2 or 3 fluorine and / or chlorine atoms or with 0 or 1 group selected from C1-C2 alkoxy, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylthio and furanyl; or is C2-C4 alkynyl or C3-C6 cycloalkyl-C1-C3 alkyl;

[0746] R g It is a C1-C3 alkyl group; or two R atoms bonded to the same carbon atom. g Together they form a methylene group (=CH2);

[0747] R h It is a C1-C3 alkyl group substituted with 0 or 1 cyano group; or a C2-C4 alkynyl group;

[0748] n is 0, 1, or 2;

[0749] q can be 1, 2, 3, 4, 5, or 6;

[0750] u is 0, 1, or 2;

[0751] v is 0 or 1;

[0752] w is 0 or 1;

[0753] x is 0 or 1;

[0754] The condition is that the sum of u, v, w, and x is 1 or 2.

[0755] Further preferred embodiments (II-I.IV) of the compound of formula (I) are the following compounds, wherein (II): R 1 R 9 For hydrogen:

[0756]

[0757] (I.II): R 1 For hydrogen, R 9 Methyl:

[0758]

[0759] (I.III): R 1 Methyl, R 9 Methyl:

[0760]

[0761] (I.IV): R 1 Methyl, R 9 For hydrogen:

[0762]

[0763] Particularly preferred compound (IIa), wherein R 1 R 2 R 6 and R 9 For hydrogen:

[0764]

[0765] Compound of formula (IIb) is also particularly preferred, wherein R 1 R 2 R 4 R 6 and R 9 For hydrogen:

[0766]

[0767] Particularly preferred compounds (IIc), wherein R 1 R 2 R 6 and R 9 Hydrogen, X is a bond (X 0 And Y is Z:

[0768]

[0769] Also particularly preferred are compounds of formula (IId), wherein R 1 R2 R 4 R 6 and R 9 Hydrogen, X is a bond (X 0 And Y is Z:

[0770]

[0771] Compounds of formula (I.II.a.) are particularly preferred, wherein R 1 R 2 R 6 It is hydrogen and R 9 Methyl:

[0772]

[0773] Compounds of formula (I.II.b.) are particularly preferred, wherein R 1 R 2 R 4 R 6 It is hydrogen and R 9 Methyl:

[0774]

[0775] Compounds of formula (I.III.a.) are particularly preferred, wherein R 2 R 6 It is hydrogen and R 1 R 9 Methyl:

[0776]

[0777] Compounds of formula (I.III.b.) are particularly preferred, wherein R 2 R 4 R 6 It is hydrogen and R 1 R 9 Methyl:

[0778]

[0779] Compounds of formula (I.IV.a.) are particularly preferred, wherein R 1 It is methyl and R 2 R 6 and R 9 For hydrogen:

[0780]

[0781] Also particularly preferred are compounds of formula (I.IV.b.), wherein R 1 It is methyl and R 2 R 4R 6 and R 9 For hydrogen:

[0782]

[0783] In the context of this invention, compounds of formula (I) are particularly preferred, wherein R 1 R 2 R 6 and R 9 It is hydrogen and R 3 R 4 R 5 and W (W through R) 7 and R 8 (Formed together with the carbon atoms they are bonded to) has the meaning defined in rows 1-2541 of Table 1 below. In R 7 and R 8 When the carbon atom bonded to form W is a chiral center, both enantiomers and mixtures thereof are the subject of this invention.

[0784] Table 1:

[0785]

[0786]

[0787]

[0788]

[0789]

[0790]

[0791]

[0792]

[0793]

[0794]

[0795]

[0796]

[0797]

[0798]

[0799]

[0800]

[0801]

[0802]

[0803]

[0804]

[0805]

[0806]

[0807]

[0808]

[0809]

[0810]

[0811]

[0812]

[0813]

[0814]

[0815]

[0816]

[0817] *) The variables A.1-A.11 representing W in Table 1 above have the following meanings:

[0818]

[0819] The following compounds I.1-I.118 are particularly preferred, which are compounds of formula (I), wherein the substituent R 1 R 2 R 6 and R 9 Both are hydrogen.

[0820] Particularly preferred compound I.1, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.1.1-I.1.2541:

[0821]

[0822] Particularly preferred compound I.2, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.2.1-I.2.2541:

[0823]

[0824] Particularly preferred compound I.3, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.3.1-I.3.2541:

[0825]

[0826] Particularly preferred compound I.4, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.4.1-I.4.2541:

[0827]

[0828] Particularly preferred compound I.5, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.5.1-I.5.2541:

[0829]

[0830] Particularly preferred compound I.6, wherein R 3R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.6.1-I.6.2541:

[0831]

[0832] Particularly preferred compound I.7, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.7.1-I.7.2541:

[0833]

[0834] Particularly preferred compound I.8, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.8.1-I.8.2541:

[0835]

[0836] Particularly preferred compound I.9, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.9.1-I.9.2541:

[0837]

[0838] Particularly preferred compound I.10, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.10.1-I.10.2541:

[0839]

[0840] Particularly preferred compound I.11, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.11.1-I.11.2541:

[0841]

[0842] Particularly preferred compound I.12, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.12.1-I.12.2541:

[0843]

[0844] Particularly preferred compound I.13, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.13.1-I.13.2541:

[0845]

[0846] Particularly preferred compound I.14, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.14.1-I.14.2541:

[0847]

[0848] Particularly preferred compound I.15, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.15.1-I.15.2541:

[0849]

[0850] Particularly preferred compound I.16, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.16.1-I.16.2541:

[0851]

[0852] Particularly preferred compound I.17, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.17.1-I.17.2541:

[0853]

[0854] Particularly preferred compound I.18, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.18.1-I.18.2541:

[0855]

[0856] Particularly preferred compound I.19, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.19.1-I.19.2541:

[0857]

[0858] Particularly preferred compound I.20, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.20.1-I.20.2541:

[0859]

[0860] Particularly preferred compound I.21, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.21.1-I.21.2541:

[0861]

[0862] Particularly preferred compound I.22, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.22.1-I.22.2541:

[0863]

[0864] Particularly preferred compound I.23, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.23.1-I.23.2541:

[0865]

[0866] Particularly preferred compound I.24, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.24.1-I.24.2541:

[0867]

[0868] Particularly preferred compound I.25, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.25.1-I.25.2541:

[0869]

[0870] Particularly preferred compound I.26, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.26.1-I.26.2541:

[0871]

[0872] Particularly preferred compound I.27, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.27.1-I.27.2541:

[0873]

[0874] Particularly preferred compound I.28, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.28.1-I.28.2541:

[0875]

[0876] Particularly preferred compound I.29, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.29.1-I.29.2541:

[0877]

[0878] Particularly preferred compound I.30, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.30.1-I.30.2541:

[0879]

[0880] Particularly preferred compound I.31, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.31.1-I.31.2541:

[0881]

[0882] Particularly preferred compound I.32, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.32.1-I.32.2541:

[0883]

[0884] Particularly preferred compound I.33, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.33.1-I.33.2541:

[0885]

[0886] Particularly preferred compound I.34, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.34.1-I.34.2541:

[0887]

[0888] Particularly preferred compound I.35, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.35.1-I.35.2541:

[0889]

[0890] Particularly preferred compound I.36, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.36.1-I.36.2541:

[0891]

[0892] Particularly preferred compound I.37, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.37.1-I.37.2541:

[0893]

[0894] Particularly preferred compound I.38, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.38.1-I.38.2541:

[0895]

[0896] Particularly preferred compound I.39, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.39.1-I.39.2541:

[0897]

[0898] Particularly preferred compound I.40, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.40.1-I.40.2541:

[0899]

[0900] Particularly preferred compound I.41, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.41.1-I.41.2541:

[0901]

[0902] Particularly preferred compound I.42, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.42.1-I.42.2541:

[0903]

[0904] Particularly preferred compound I.43, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.43.1-I.43.2541:

[0905]

[0906] Particularly preferred compound I.44, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.44.1-I.44.2541:

[0907]

[0908] Particularly preferred compound I.45, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.45.1-I.45.2541:

[0909]

[0910] Particularly preferred compound I.46, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.46.1-I.46.2541:

[0911]

[0912] Particularly preferred compound I.47, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.47.1-I.47.2541:

[0913]

[0914] Particularly preferred compound I.48, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.48.1-I.48.2541:

[0915]

[0916] Particularly preferred compound I.49, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.49.1-I.49.2541:

[0917]

[0918] Particularly preferred compound I.50, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.50.1-I.50.2541:

[0919]

[0920] Particularly preferred compound I.51, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.51.1-I.51.2541:

[0921]

[0922] Particularly preferred compound I.52, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.52.1-I.52.2541:

[0923]

[0924] Particularly preferred compound I.53, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.53.1-I.53.2541:

[0925]

[0926] Particularly preferred compound I.54, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.54.1-I.54.2541:

[0927]

[0928] Particularly preferred compound I.55, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.55.1-I.55.2541:

[0929]

[0930] Particularly preferred compound I.56, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.56.1-I.56.2541:

[0931]

[0932] Particularly preferred compound I.57, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.57.1-I.57.2541:

[0933]

[0934] Particularly preferred compound I.58, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.58.1-I.58.2541:

[0935]

[0936] Particularly preferred compound I.59, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.59.1-I.59.2541:

[0937]

[0938] Particularly preferred compound I.60, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.60.1-I.60.2541:

[0939]

[0940] Particularly preferred compound I.61, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.61.1-I.61.2541:

[0941]

[0942] Particularly preferred compound I.62, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.62.1-I.62.2541:

[0943]

[0944] Particularly preferred compound I.63, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.63.1-I.63.2541:

[0945]

[0946] Particularly preferred compound I.64, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.64.1-I.64.2541:

[0947]

[0948] Particularly preferred compound I.65, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.65.1-I.65.2541:

[0949]

[0950] Particularly preferred compound I.66, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.66.1-I.66.2541:

[0951]

[0952] Particularly preferred compound I.67, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.67.1-I.67.2541:

[0953]

[0954] Particularly preferred compound I.68, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.68.1-I.68.2541:

[0955]

[0956] Particularly preferred compound I.69, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.69.1-I.69.2541:

[0957]

[0958] Particularly preferred compound I.70, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.70.1-I.70.2541:

[0959]

[0960] Particularly preferred compound I.71, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.71.1-I.71.2541:

[0961]

[0962] Particularly preferred compound I.72, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.72.1-I.72.2541:

[0963]

[0964] Particularly preferred compound I.73, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.73.1-I.73.2541:

[0965]

[0966] Particularly preferred compound I.74, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.74.1-I.74.2541:

[0967]

[0968] Particularly preferred compound I.75, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.75.1-I.75.2541:

[0969]

[0970] Particularly preferred compound I.76, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.76.1-I.76.2541:

[0971]

[0972] Particularly preferred compound I.77, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.77.1-I.77.2541:

[0973]

[0974] Particularly preferred compound I.78, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.78.1-I.78.2541:

[0975]

[0976] Particularly preferred compound I.79, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.79.1-I.79.2541:

[0977]

[0978] Particularly preferred compound I.80, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.80.1-I.80.2541:

[0979]

[0980] Particularly preferred compound I.81, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.81.1-I.81.2541:

[0981]

[0982] Particularly preferred compound I.82, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.82.1-I.82.2541:

[0983]

[0984] Particularly preferred compound I.83, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.83.1-I.83.2541:

[0985]

[0986] Particularly preferred compound I.84, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.84.1-I.84.2541:

[0987]

[0988] Particularly preferred compound I.85, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.85.1-I.85.2541:

[0989]

[0990] Particularly preferred compound I.86, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.86.1-I.86.2541:

[0991]

[0992] Particularly preferred compound I.87, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.87.1-I.87.2541:

[0993]

[0994] Particularly preferred compound I.88, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.88.1-I.88.2541:

[0995]

[0996] Particularly preferred compound I.89, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.89.1-I.89.2541:

[0997]

[0998] Particularly preferred compound I.90, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.90.1-I.90.2541:

[0999]

[1000] Particularly preferred compound I.91, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.91.1-I.91.2541:

[1001]

[1002] Particularly preferred compound I.92, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.92.1-I.92.2541:

[1003]

[1004] Particularly preferred compound I.93, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.93.1-I.93.2541:

[1005]

[1006] Particularly preferred compound I.94, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.94.1-I.94.2541:

[1007]

[1008] Particularly preferred compound I.95, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.95.1-I.95.2541:

[1009]

[1010] Particularly preferred compound I.96, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.96.1-I.96.2541:

[1011]

[1012] Particularly preferred compound I.97, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.97.1-I.97.2541:

[1013]

[1014] Particularly preferred compound I.98, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.98.1-I.98.2541:

[1015]

[1016] Particularly preferred compound I.99, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.99.1-I.99.2541:

[1017]

[1018] Particularly preferred compound I.100, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.100.1-I.100.2541:

[1019]

[1020] Particularly preferred compound I.101, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.101.1-I.101.2541:

[1021]

[1022] Particularly preferred compound I.102, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.102.1-I.102.2541:

[1023]

[1024] Particularly preferred compound I.103, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.103.1-I.103.2541:

[1025]

[1026] Particularly preferred compound I.104, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.104.1-I.104.2541:

[1027]

[1028] Particularly preferred compound I.105, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.105.1-I.105.2541:

[1029]

[1030] Particularly preferred compound I.106, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.106.1-I.106.2541:

[1031]

[1032] Particularly preferred compound I.107, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.107.1-I.107.2541:

[1033]

[1034] Particularly preferred compound I.108, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.108.1-I.108.2541:

[1035]

[1036] Particularly preferred compound I.109, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) has the meaning defined in rows 1-2541 of Table 1 above, i.e., for each compound I.109.1-I.109.2541:

[1037]

[1038] Particularly preferred compound I.110, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.110.1-I.110.2541:

[1039]

[1040] Particularly preferred compound I.111, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.111.1-I.111.2541:

[1041]

[1042] Particularly preferred compound I.112, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.112.1-I.112.2541:

[1043]

[1044] Particularly preferred compound I.113, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to, they form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.113.1-I.113.2541:

[1045]

[1046] Particularly preferred compound I.114, wherein R 3 R 4 R 5 and R 7 R 8(Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.114.1-I.114.2541:

[1047]

[1048] Particularly preferred compound I.115, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.115.1-I.115.2541:

[1049]

[1050] Particularly preferred compound I.116, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.116.1-I.116.2541:

[1051]

[1052] Particularly preferred compound I.117, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.117.1-I.117.2541:

[1053]

[1054] Particularly preferred compound I.118, wherein R 3 R 4 R 5 and R 7 R 8 (Together with the carbon atoms they are bonded to form W) have the meanings defined in rows 1-2541 of Table 1 above, i.e., for each compound I.118.1-I.118.2541:

[1055]

[1056] Compounds of formula (I) according to the present invention can be prepared by standard organic chemistry methods, for example by the following methods:

[1057]

[1058] Compounds of formula (I) can be prepared according to methods described in the prior art or similar methods. Synthesis utilizes starting materials that are commercially available or can be prepared from readily available compounds according to conventional procedures.

[1059] Compounds of formula (I) can be prepared from carboxylic acids (III) and commercially available amines (II) using an organic base and a coupling agent. Therefore, compounds of formula (I) can be synthesized from the corresponding carboxylic acid (1 eq.) using a coupling agent (1-2 eq.) such as T3P (propanephosphonic anhydride) or HATU (O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethylurea hexafluorophosphate), an organic base (1-3 eq.), and an amine (II) (1-3 eq.). The reaction is generally carried out in an organic solvent. Aprotic organic solvents are preferred. Tetrahydrofuran (THF), N,N-dimethylformamide (DMF), or acetonitrile (ACN) are most preferred. The reaction is carried out at a temperature between 0°C and reflux. The reaction is preferably carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine.

[1060]

[1061] Carboxylic acid (III) can be commercially available or can be derived from the corresponding ester (IV) (wherein R) P It is prepared by (either alkyl or benzyl). If R P If it is an alkyl group, the ester (IV) can be cleaved using an aqueous solution of an alkali metal hydroxide. Lithium hydroxide, sodium hydroxide, or potassium hydroxide (1-2 eq.) is preferred. The reaction is typically carried out in a mixture of water and an organic solvent. Preferably, the organic solvent is THF, methanol, or acetonitrile. The reaction is carried out at a temperature of 0-100°C. Preferably, the reaction is carried out at room temperature. If R in (IV) p If the ester is benzyl, it can be cleaved using carbon-supported palladium (0.001-1 eq.) as a catalyst and hydrogen at a temperature between 0°C and reflux. The reaction is preferably carried out at room temperature. Organic solvents are typically used. THF, methanol, or ethanol are preferred.

[1062]

[1063] The cyclic compounds of formula (IV) can be prepared from a cyclic carboxylic acid (VI) and a commercially available amine (V) using a base and a coupling agent. Therefore, compounds of formula (IV) can be synthesized from the corresponding carboxylic acid (1 eq.) using a coupling agent (1-2 eq.) such as T3P (propanephosphonic anhydride) or HATU (O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethylurea hexafluorophosphate), an organic base (1-3 eq.), and an amine (V) (1-3 eq.). The reaction is typically carried out in an organic solvent. Aprotic organic solvents are preferred. Tetrahydrofuran (THF), N,N-dimethylformamide (DMF), or acetonitrile (ACN) are most preferred. The reaction is carried out at a temperature between 0 °C and reflux temperature.

[1064] The reaction is preferably carried out at room temperature. Preferably, the organic base is triethylamine or N,N-diisopropylethylamine.

[1065]

[1066] Cyclic carboxylic acids (VI) can be prepared from the corresponding diester by selectively cleaving one ester group. If R q If the ester is an alkyl ester, selective ester cracking can be achieved using an aqueous alkali. Alkali metal hydroxides are preferred. Lithium hydroxide, sodium hydroxide, or potassium hydroxide are most preferred. The reaction is typically carried out in a mixture of water and an organic solvent. THF, methanol, or acetonitrile are preferred. The reaction is carried out at a temperature of 0-100°C, preferably at room temperature.

[1067] Alternatively, trimethyltin hydroxide (e.g., 1 eq.) in 1,2-dichloroethane at room temperature to reflux (as described in Angew. Chem. Int. Ed., 2005, 44: 1378-1382) can be used, preferably under reflux. If R in (VII) q If the ester is benzyl, then carbon-supported palladium (0.001-1 eq.) can be used as a catalyst and hydrogen can be used to cleave the ester at a temperature between 0°C and reflux. The reaction is preferably carried out at room temperature.

[1068] Organic solvents are typically used. THF, methanol, or ethanol are preferred.

[1069]

[1070] The cyclic diester (VII) can be synthesized from a commercially available cyclic monoester (VIII), a base, and a chloroformate (IX) (1-3 eq.), as described in Bioorganic & Medicinal Chemistry Letters, 12(11), 1501-1505; 2002. The reaction is typically carried out in an organic solvent, preferably in tetrahydrofuran. A suitable temperature is from -78°C to 25°C. Preferably, the reaction is heated from -78°C to 25°C over 16 hours. Lithium diisopropylamino (1 eq.) is preferably used as the base.

[1071] Alternatively, specific cyclic diesters can be prepared according to the following process:

[1072]

[1073] Alternatively, the cyclic diester (VIIa) can be prepared from commercially available diethyl dibromomalonate (Xa), a base, and an alcohol or thiol of formula (XI) (V is -CH2CH2- or -CH2CH2CH2-, optionally modified by R). g Substitution; and A is independently selected from OH, SH, NR d The reaction is typically carried out in an organic solvent, preferably in tetrahydrofuran. A suitable temperature range is between 0°C and 25°C. Sodium hydride (2 eq.) is preferably used as the base.

[1074]

[1075] The cyclic diester of formula (VIIb) containing an oxygen heterocycle is commercially available or can be produced by the corresponding diazo compound (Xb) using dirhodium tetraacetate ([Rh(OAc)2]2)(0.001-0.1 eq.) and a commercially available halohydrin (Hal=Cl, Br) of formula (XII) (V being -CH2CH2-, -CH2CH2CH2-, -CH2CH2CH2CH2-, optionally modified by R g The substituted form is then cyclized in N,N-dimethylformamide (DMF) using sodium hydride (1.2 eq.), as described in Angew. Chem. Int. Ed. 2014, 53, 14230-14234.

[1076]

[1077] Alternatively, the cyclic unsaturated diester of formula (VIIc) containing an oxoheterocyclic ring can be produced by the corresponding diazo compound (Xb) using dirhodium tetraacetate ([Rh(OAc)2]2) (0.001-0.1 eq.) and an alcohol of formula (XIII) (U being -CH2- or -CH2CH2-, optionally with R gIt is prepared by cyclization in acetonitrile using cesium carbonate (2.0 eq.) as a substitute. The suitable temperature range is from room temperature to 60 °C.

[1078]

[1079] Cyclic diesters containing N-heterocycles (VIId) can be produced by the corresponding diazo compound (Xb) using bis[rhodium(α,α,α′,α′-tetramethyl-1,3-phenylenediol)]([Rh(esp)]2, CAS[819050-89-0](0.001-0.1eq.) and halogenated amines of formula (XIV) (Hal = Br, Cl) (V is -CH2CH2-, -CH2CH2CH2- or -CH2CH2CH2CH2-, optionally R g (The substituted) was prepared by adding cesium hydroxide monohydrate (2 eq.) and tetrabutylammonium bromide (0.1 eq.) to toluene at 60 °C, as described in Angew. Chem. Int. Ed. 2019, 58, 1458-1462.

[1080]

[1081] The unsaturated diester containing an O-heterocycle of formula (VIIe) (U being -CH2- or -CH2CH2-) can be prepared from commercially available ketomalonate (CAS 609-09-6) (Xc) using cyclic or acyclic dienes of formula (XV) in acetonitrile at 130 °C, as described in J.Org.Chem.1977,42,4095-4103.

[1082] Alternatively, the reaction mixture can be heated at 130°C for 4 hours by irradiating it with microwaves (300W).

[1083]

[1084] The corresponding N-heterocyclic unsaturated diester of formula (VIIf) (U being -CH2- or -CH2CH2-) can be similarly prepared from the corresponding iminomalonate (Xd) using cyclic or acyclic dienes of formula (XV) in tetrahydrofuran at 100 °C, as described in Tetrahedron Lett. 1981, 22, 4607, Synth. Commun. 1972, 2, 211 and J. Med. Chem. 1973, 16, 853, or by irradiating the reaction mixture with microwaves (100 °C, 4 hours, 300 W).

[1085]

[1086] The diester containing the epoxide of formula (VIIg) can be prepared from a commercially available olefin of formula (Xe) in ethanol using sodium tungstate dihydrate (CAS 13472-45-2) and hydrogen peroxide (40% aqueous solution), as described in Tetrahedron 2010, 66, 9401-9404.

[1087]

[1088] The corresponding aziridine of formula (VIIh) can be obtained by using sodium azide and ammonium chloride in a di- epoxide of formula (Xf). It is prepared by reduction with triphenylphosphine in an aqueous solution of alkane and then in acetonitrile, as described in Tetrahedron 2010, 66, 9401-9404.

[1089]

[1090] The corresponding triazoline of formula (VIIi) can be prepared from a commercially available olefin of formula (Xe) using an azide of formula (XVI) at 60 °C with a catalytic amount of N,N-dimethylurea in toluene, as described in Org. Lett. 2015, 17, 4568-4571.

[1091]

[1092] The corresponding aziridine of formula (VIIj) can be prepared from the triazoline of formula (VIIi) as a solid or in solution by irradiation with a wavelength λ ≥ 220 nm, as described in Org. Lett. 2015, 17, 4568-4571.

[1093] To broaden the spectrum of action, the compound of formula (I) can be mixed with representatives of many other herbicidal or plant growth-regulating active ingredients and then applied simultaneously. Suitable components for combination include, for example, herbicides selected from the following categories: acetamides, amides, aryloxyphenoxypropionates, benzamides, benzofurans, benzoic acids, benzothiadiazinones, and bipyridines. Carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenols, diphenyl ethers, glycines, imidazolinones, isocyanates azoles, isotonic Alzolidine ketones, nitriles, N-phenylbenzodicarboximides, diazoles, Alzolidinediones, hydroxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, hypophosphino acids, aminophosphates, dithiophosphates, o-carbamoylbenzoates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridine carboxamides, pyrimidinediones, pyrimidine (thio)benzoates, quinolinecarboxylic acids, amine ureas, sulfonamide carbonyl triazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones, triazolocarboxamides, triazolopyrimidines, triones, uracils, and ureas.

[1094] Furthermore, it may be beneficial to apply Formula (I) compounds alone or in combination with other herbicides or in mixtures with other crop protectants, such as with agents for controlling pests or plant pathogenic fungi or bacteria. Also of interest is the miscibility with solutions of inorganic salts used to treat nutrient and trace element deficiencies. Other additives, such as non-vegetarian toxic oils and oil concentrates, may also be added.

[1095] In one embodiment of the invention, the present invention comprises at least one compound of formula (I) (compound A or component A) and at least one other active compound selected from herbicide B (compound B), preferably herbicide B of group b1)-b15) and safener C (compound C).

[1096] In another embodiment of the invention, the present invention comprises at least one compound of formula (I) and at least one other active compound B (herbicide B).

[1097] Examples of herbicides B that can be used in combination with compound A of formula (I) of the present invention include:

[1098] b1) Selected from the following lipid biosynthesis inhibitors: ACC herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, and diclofop-methyl. fenoxaprop fenoxaprop-ethyl, high Fenoxaprop-P, high Fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, 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 1312337-72-6), 4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1033757-93-5 ... 1312340-84-3), 5-acetoxy-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312337-48-6), 5-acetoxy-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one, 5-acetoxy-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1), 5-acetoxy-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2), 4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,Methyl 6-tetramethyl-5-oxo-2H-pyran-3-ylcarboxylate (CAS) 1312337-51-1), methyl 4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carboxylate, methyl 4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carboxylate (CAS1312340-83-2), methyl 4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carboxylate (CAS 1033760-58-5); and non-ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate, and vernolate;

[1099] b2) Selected ALS inhibitors from the following: sulfonylureas, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-met hyl), ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-me thyl-sodium), iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, fluoropropiosulfuron Prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfurosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methylTrifloxysulfuron, triflusulfuron, triflusulfuron-methyl, and tritosulfuron; imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, and imazethapyr; triazolopyrimidine herbicides; and sulfonylanilines such as cloransulam, cloransulam-methyl, diclosulam, and flumets. ulam), florasulam, metosulam, penoxsulam, pyrimisulfan, and pyroxsulam; pyrimidinyl benzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, and 1-methylethyl 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate (CAS 1-methylethyl ester) 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]propyl benzoate (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylamine (CAS 420138-01-8), sulfonylaminocarbonyl triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl, and triafamone; wherein preferred embodiments of the invention relate to compositions comprising at least one imidazolinone herbicide;

[1100] b3) Selected from the following photosynthesis inhibitors: amicabazone, photosynthetic system II inhibitors, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrole-5-one (CAS 1654744-66-7), 1-(5-tert-butylisothiazolinone) (3-azolyl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrole-5-one (CAS 1637455-12-9), 1-(5-tert-butylisothiazolinone) 1-(5-tert-butyl-1-methylpyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrolo-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methylpyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrolo-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methylpyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrolo-5-one (CAS 1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-trifluoromethyl-2-pyridinyl]imidazolidine-2-one (CAS 2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidine-2-one (CAS2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidine-2-one (CAS1701416-69-4), 4-hydroxy-1-methyl-3-[4-trifluoromethyl-2-pyridyl]imidazolidine-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-trifluoromethylpyrazol-3-yl]imidazolidine-2-one (CAS2023785-80-8), 1-(5-tert-butylisocyanate) (3-yl)-4-ethoxy-5-hydroxy-3-methylimidazolidine-2-one (CAS 1844836-64-1), a triazine herbicide, including chlorotriazines, triazinones, triazindiones, methylthiotriazines, and pyridazinones, such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone, and metribuzin. Herbicides such as uzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, and trietazin; arylureas such as chlorobromuron, chlorotoluron, chloroxuron, and butyl... Dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron, and thidiazuron; phenylcarbamates such as desmedipham, karbutilat, phenmedipham, and phenmedipham-ethyl The herbicides include nitrile herbicides such as bromofenoxim, bromoxynil and their salts and esters, ioxynil and their salts and esters; uracil herbicides such as bromacil, lenacil and terbacil; bentazon and bentazon-sodium; pyridate, pyridafol, pentanochlor and propanil; and photosynthetic system I inhibitors such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate. Preferred embodiments of the invention relate to compositions comprising at least one arylurea herbicide. Preferred embodiments of the invention also relate to compositions comprising at least one triazine herbicide. The preferred embodiments of the present invention also relate to those compositions comprising at least one nitrile herbicide;

[1101] b4) Selected from the following protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, and flu... Flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactoferrin, propargite Oxadiargyl, oxadiazon, oxyfluorfen, and pendimethalin Pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridinoxy]ethyl acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 353292-31-6; S-3100) 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4] [1,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[b][1,4]) (-6-azinyl)-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]) Methyl 2,4-dione (CAS 1304113-05-0), (E)-4-[2-chloro-5-(4-chloro-5-difluoromethoxy-1H-methylpyrazol-3-yl)-4-fluorophenoxy]-3-methoxybut-2-enoate (CAS 948893-00-3), 3-[7-chloro-5-fluoro-2-trifluoromethyl-1H-benzimidazol-4-yl]-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (CAS 212754-02-4), methyl 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4-fluorophenoxy]-2-methoxyacetate (CAS 1304113-05-0), methyl ... 1970221-16-9), methyl acetate of 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate (CAS2158274-96-3), ethyl acetate of 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetate (CAS 158274-50-9), methyl acetate of 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenoxy]-2-pyridyl]oxy]ethyl acetate (CAS 2271389-22-9), ethyl acetate of 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenoxy]-2-pyridyl]oxy] 2230679-62-4), methyl acetate of 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetate (CAS 2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]ethyl acetate (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methanesulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-Dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methanesulfonyl)-acetamide (CAS 2158276-22-1);

[1102] b5) Selected from the following bleaching herbicides: PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7); HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clonazol, fenquintrione, and isoxaflutole. Fluoride (isoxaflutole), mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, bleaching agents, unknown targets: aclonifen, amitrol, flumeturon, 2-chloro-3-methylthio-N-(1-methyltetrazole-5-yl)-4-trifluoromethylbenzamide (CAS 1361139-71-0), dichloroisocyanurate Bixlozone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isocyanate Azoxystrobin (CAS 81778-66-7);

[1103] b6) Selected from the following EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyphosate potassium, and glyphosate-trimesium (sulfosate).

[1104] b7) Selected from the following glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, and glufosinate-ammonium.

[1105] b8) Selected from the following DHP synthase inhibitors: asulam;

[1106] b9) Selected from the following mitotic inhibitors: K1 group compounds: dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, and trifluralin; aminophosphates such as amiprophos, amiprophos-methyl, and butamiphos; benzoic acid herbicides such as chlorthal and chlorpyrifos. Orthal-dimethyl), pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam, K2 group compounds: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, and propham; among which K1 group compounds are preferred, especially dinitroanilines;

[1107] b10) is selected from the following VLCFA inhibitors: chloroacetamides such as acetochlor, alachlor, midochlor, butachlor, dimethachlor, dimethanamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor, and thenylchlor; oxyacetanilides... etanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide, and napropamide-M, tetrazolinones such as fentrazamide, and other herbicides such as ailofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, and isocyanates of formulas II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8, and II.9. Azoline compounds:

[1108]

[1109] Equation (II) Azoline compounds are known in the art, for example by WO 2006 / 024820, WO2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576;

[1110] Among VLCFA inhibitors, chloroacetamides and hydroxyacetamides are preferred;

[1111] b11) is selected from the following cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indazon, isoxaben, triaziflam, and 1-cyclohexyl-5-pentafluorophenoxy-1 4-[1,2,4,6]thiatriazine-3-ylamine (CAS 175899-01-1);

[1112] b12) is selected from the following decoupling herbicides: dinoseb, dinoterb, and dinitrocresol (DNOC) and their salts;

[1113] b13) Selected from the following plant growth regulator herbicides: 2,4-D and its salts and esters, such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxy-propyl)ammonium and its esters, benzolin, benzolin-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, floppyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS) 943832-60-8), MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA(2,3,6) and its salts and esters, triclipyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS1390661-72-9), and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridinecarboxylic acid (CAS 1629965-65-6);

[1114] b14) is selected from the following plant auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam, and naptalam-sodium;

[1115] b15) Selected from the following herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 15)

[1116] 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, sodium DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methylbromide, methyl-dymron, methyl iodomethyl iodide), sodium formarsine (MSMA), oleic acid, chloride Oxaziclomefone, pelargonic acid, pyributicarb, and quinoclamine

[1117] tetflupyrolimet and tridiphane.

[1118] Furthermore, it may be useful to apply the compound of formula (I) in combination with a safener. A safener is a compound that prevents or reduces damage to the beneficial plant but does not significantly affect the herbicidal effect of the compound of formula (I) on the unwanted plant. They can be applied before sowing (e.g., at seed treatment, on shoots or seedlings) or pre- or post-emergence of the beneficial plant. The safener and the compound of formula (I), and optionally, herbicide B, can be applied simultaneously or sequentially.

[1119] In another embodiment of the invention, the present invention combination comprises at least one compound of formula (I) and at least one safer agent C (component C).

[1120] Examples of safeners include (quinoline-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, and 4,5-dihydro-5,5-diaryl-3-isocyanate. Azoxycarboxylic acids, dichloroacetamides, α-oxime-phenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalenedicarboxylic anhydride, 2-halo-4-haloalkyl-5-thiazolium carboxylic acids, thiophosphates and N-alkyl-O-phenylcarbamates and their agriculturally usable salts and their agriculturally usable derivatives such as amides, esters and thioesters, provided that they have an acid group.

[1121] Examples of safener compound C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, and bisbenzyl. Isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-dichloroacetyl-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-dichloroacetyl-1,3- Zolpidem (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).

[1122] Active compounds B and C of groups b1)-b15) are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http: / / www.alanwood.net / pesticides / ); Farm Chemicals Handbook 2000, Vol. 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R.R. Schmidt, Herbizide, Georg Thieme Verlag, Stuttgart, 1995; W.H. Ahrens, Herbicide Handbook, 7th ed., Weed Science Society of America, 1994; and K.K. Hatzios, Herbicide Handbook, 7th ed., Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-dichloroacetyl-1,3- Azoxyl [CAS No. 52836-31-4] is also known as R-29148. 4-Dichloroacetyl-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also known as AD-67 and MON 4660.

[1123] The attribution of an active compound to its corresponding mechanism of action is based on existing knowledge. If several mechanisms of action apply to an active compound, then the substance is attributed to only one mechanism of action.

[1124] The present invention also relates to formulations comprising at least one adjuvant and at least one compound of formula (I) of the present invention.

[1125] The formulation contains an effective amount of a compound of formula (I). The term "effective amount" refers to the amount of a combination or compound of formula (I) sufficient to control unwanted plants, especially in crops (i.e., cultivated plants), without causing significant damage to the treated crop. This amount can vary over a wide range and depends on various factors such as the unwanted plant to be controlled, the crop or material being treated, climatic conditions, and the specific compound of formula (I) used.

[1126] Compounds of formula (I) or their salts can be converted into formulations commonly used in pharmaceutical preparations, such as solutions, emulsions, suspensions, powders, pastes, granules, molded products, capsules, and mixtures thereof. Examples of formulation types include suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, tablets, wettable powders or granules (e.g., WP, SP, WS, DP, DS), molded products (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations for treating plant propagation materials such as seeds (e.g., GF). These and other formulation types are defined in “Catalogue of pesticide formulation types and international coding system,” Technical Monograph, Vol. 2, 6th edition, May 2008, CropLife International.

[1127] Formulations such as Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, AgrowReports DS243, T&F Informa, London, 2005, are prepared in a known manner.

[1128] Suitable additives include solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliary agents, solvents, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, tackifiers and binders.

[1129] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling point mineral oil fractions, such as kerosene and diesel; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene, and alkylated naphthalene; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, and cyclohexanol; diols; DMSO; ketones, such as cyclohexanone; esters, such as lactates, carbonates, fatty acid esters, and γ-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone and fatty acid dimethylamide; and mixtures thereof.

[1130] Suitable solid carriers or fillers are mineral soils, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, and magnesium oxide; polysaccharides, such as cellulose and starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and urea; and plant-derived products, such as grain flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

[1131] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. These surfactants can be used as emulsifiers, dispersants, solvents, wetting agents, penetration enhancers, protective colloids, or auxiliaries. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[1132] Suitable anionic surfactants are alkali metal, alkaline earth metal, or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, and carboxylic acids, as well as mixtures thereof. Examples of sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamides. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols, or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[1133] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated by 1-50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucosamides or fatty acid chain alkanolamides. Examples of esters are fatty acid esters, glycerides, or monoglycerides. Examples of glycosyl surfactants are sorbitol, ethoxylated sorbitol, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[1134] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers containing blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers containing alkanols, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyvinylamine.

[1135] Suitable adjuvants are compounds that possess negligible pesticide activity or even no pesticide activity themselves, but which improve the biological properties of the target analyte. Examples are surfactants, mineral or vegetable oils, and other adjuvants. Other examples are listed in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[1136] Suitable thickeners are polysaccharides (such as xanthan gum and carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[1137] Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

[1138] Suitable antifreeze agents include ethylene glycol, propylene glycol, urea, and glycerin.

[1139] Suitable defoamers are polysiloxanes, long-chain alcohols, and fatty acid salts.

[1140] Suitable colorants (e.g., red, blue, or green) are low-water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titanium dioxide, ferric hexacyanate ferrite) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants).

[1141] Suitable tackifiers or adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biowax or synthetic wax, and cellulose ether.

[1142] Examples of formulation types and their preparation are as follows:

[1143] i) Water-soluble concentrates (SL, LS)

[1144] Dissolve 10-60% by weight of the compound of formula (I) of the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 5-15% by weight of a wetting agent (e.g., an alcohol alkoxylate) in water and / or a water-soluble solvent (e.g., an alcohol) added to 100% by weight. The active substance dissolves upon dilution with water.

[1145] ii) Dispersible concentrate (DC)

[1146] Dissolve 5-25% by weight of the compound of formula (I) of the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 1-10% by weight of a dispersant (e.g., polyvinylpyrrolidone) in an organic solvent (e.g., cyclohexanone) added to 100% by weight. Dilute with water to obtain a dispersion.

[1147] iii) Emulsifiable concentrate (EC)

[1148] 15-70% by weight of a compound of formula (I) of the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) and 5-10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) is dissolved in a water-insoluble organic solvent (e.g., an aromatic hydrocarbon) added to 100% by weight. The emulsion is then diluted with water.

[1149] iv) Emulsions (EW, EO, ES)

[1150] 5-40% by weight of a compound of formula (I) of the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C), and 1-10% by weight of an emulsifier (e.g., calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbons). The mixture is introduced into 100% by weight of water using an emulsifier to form a homogeneous emulsion. The emulsion is then diluted with water.

[1151] v) Suspension (SC, OD, FS)

[1152] In a stirred ball mill, 20-60 wt% of a compound of formula (I) of the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C), are added to a dispersant and wetting agent (e.g., sodium lignin sulfonate and alcohol ethoxylate), 0.1-2 wt% of a thickener (e.g., xanthan gum), and up to 100 wt% of water for underwater milling to obtain a finely ground active substance suspension. The suspension is diluted with water to obtain a stable active substance suspension. For FS type formulations, up to 40 wt% of a binder (e.g., polyvinyl alcohol) is added.

[1153] vi) Water-dispersible particles and water-soluble particles (WG, SG)

[1154] 50-80% by weight of the compound of formula (I) of the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C), is finely milled with the addition of up to 100% by weight of a dispersant and wetting agent (e.g., sodium lignin sulfonate and alcohol ethoxylate) and prepared into water-dispersible or water-soluble granules using industrial equipment (e.g., extruder, spray tower, fluidized bed). Diluting with water yields a stable dispersion or solution of the active substance.

[1155] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[1156] 50-80% by weight of a compound of formula (I) of the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C), is milled in a rotor-stator mill with the addition of 1-5% by weight of a dispersant (e.g., sodium lignin sulfonate), 1-3% by weight of a wetting agent (e.g., alcohol ethoxylate), and up to 100% by weight of a solid carrier (e.g., silica gel). The mixture is diluted with water to obtain a stable dispersion or solution of the active substance.

[1157] viii) Gel (GW, GF)

[1158] In a stirred ball mill, 3-10 wt% of a dispersant (e.g., sodium lignin sulfonate), 1-5 wt% of a thickener (e.g., carboxymethyl cellulose), and up to 100 wt% of 5-25 wt% of a compound of formula (I) of the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C), are added to obtain a fine suspension of the active substance. Diluting with water yields a stable suspension of the active substance.

[1159] iv) Microemulsions (ME)

[1160] Add 5-20% by weight of the compound of formula (I) of the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicide compound B (component B) and safener C (component C) to 5-30% by weight of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant blend (e.g., alcohol ethoxylate and arylphenol ethoxylate), and 100% by weight of water. Stir the mixture for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[1161] iv) Microcapsules (CS)

[1162] An oil phase comprising 5-50 wt% of a compound of formula (I) of the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C), 0-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbons), and 2-15 wt% of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound of formula (I) of the present invention, 0-40 wt% of a water-insoluble organic solvent (e.g., aromatic hydrocarbons), and an isocyanate monomer (e.g., diphenylmethane-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). The addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1-10 wt%. wt% refers to the entire CS formulation.

[1163] ix) Sprinkleable powder (DP, DS)

[1164] 1-10% by weight of the compound of formula (I) of the present invention or a combination of at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safer agent C (component C) is finely ground and thoroughly mixed with up to 100% by weight of a solid carrier (e.g., finely ground kaolin).

[1165] x) particles (GR, FG)

[1166] 0.5-30% by weight of the compound of formula (I) of the present invention, or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C), is finely ground and combined with up to 100% by weight of a solid carrier (e.g., silicate). Granulation is achieved by extrusion, spray drying, or fluidized bed.

[1167] xi) Ultra-low volume liquids (UL)

[1168] Dissolve 1-50% by weight of the compound of formula (I) of the present invention or a combination comprising at least one compound of formula (I) (component A) and at least one other compound selected from herbicidal compound B (component B) and safener C (component C) in an organic solvent (e.g., an aromatic hydrocarbon) added to 100% by weight.

[1169] Formulation types i)-xi) may optionally contain other adjuvants, such as 0.1-1% by weight of bactericide, 5-15% by weight of antifreeze, 0.1-1% by weight of defoamer and 0.1-1% by weight of colorant.

[1170] Formulations and / or combinations typically contain 0.01-95% by weight, preferably 0.1-90% by weight, and especially 0.5-75% by weight of compound (I). Compound (I) is used with a purity of 90-100%, preferably 95-100% (based on NMR spectroscopy).

[1171] For treating plant propagation material, especially seeds, seed treatment solutions (LS), suspension emulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are commonly used. These formulations, after dilution 2-10 times, provide an active ingredient concentration of 0.01-60% by weight, preferably 0.1-40% by weight, in ready-to-use formulations. (Down)

[1172] Methods of applying compounds of formula (I), their formulations, and / or combinations to plant propagation material, especially seeds, include seed dressing, coating, granulation, powdering, soaking, and furrow application. Preferably, compounds of formula (I), their formulations, and / or combinations are applied to the plant propagation material by methods that do not induce germination, such as seed dressing, granulation, coating, and powdering.

[1173] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients and other pesticides (e.g., herbicides, insecticides, fungicides, growth regulators, safeners) can be added as premixes or, if appropriate, immediately before use (in a barrel mix) to compounds of formula (I), formulations containing them, and / or combinations thereof. These agents can be mixed with the formulations of the present invention at a weight ratio of 1:100-100:1, preferably 1:10-10:1.

[1174] Users typically use compounds of formula (I) of the present invention, formulations comprising them, and / or combinations thereof in pre-dosing devices, backpack sprayers, spray cans, spray aircraft, or irrigation systems. The formulation is typically prepared to the desired application concentration with water, buffers, and / or other adjuvants to obtain a ready-to-use spray or a formulation of the present invention. 20-2000 liters, preferably 50-400 liters, of ready-to-use spray are typically applied per hectare of agricultural use area.

[1175] According to one embodiment, the user can mix the components of the formulation of the present invention or a portion of the premixed components, such as the components comprising the compound of formula (I) and optionally, the active substances selected from groups B and / or C), in a spray can, and other adjuvants and additives may be added if appropriate.

[1176] In another embodiment, the user can mix the components of the formulation of the present invention, such as the parts of a packaged kit or the parts of a binary or ternary mixture, in a spray can and, if appropriate, add other adjuvants.

[1177] In another embodiment, the components or partially premixed components of the formulation of the present invention may be applied in combination (e.g., after barrel mixing) or sequentially, such as components comprising the compound of formula (I) and optionally, active substances selected from groups B and / or C).

[1178] Compounds of formula (I) are suitable as herbicides. They are suitable either directly as suitable formulations or in combination with at least one other compound selected from herbicidal active compound B (component B) and safener C (component C).

[1179] Compounds of formula (I), or formulations and / or combinations thereof containing formula (I), are highly effective at controlling unwanted plants in non-crop areas, especially at high application rates. They act on broadleaf and grass weeds in crops such as wheat, rice, maize, soybean, and cotton without causing any significant damage to the crops. This effect is primarily observed at low application rates.

[1180] In particular, compounds of formula (I) or formulations and / or combinations thereof containing compounds of formula (I) may be used to control at least one of the following undesirable plant species: Abutilon theophrasti (ABUTH), Alopercurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Apera spica-venti (APESV), Avena fatua (AVEFA), Echinocloa crus-galli (ECHCG), Lolium multiflorum (LOLMU), Fallopia convolvulus (POLCO), Setaria viridis (SETVI), and Setaria faberi (SETFA).

[1181] Compounds of formula (I) or formulations and / or combinations thereof are applied to plants primarily by foliar spraying. Application can be made using conventional spraying techniques with a volume of approximately 100-1000 l / ha (e.g., 300-400 l / ha) using, for example, water as a carrier. Compounds of formula (I) or formulations and / or combinations thereof may also be applied by low-volume or ultra-low-volume methods or in microparticle form.

[1182] The application of compounds of formula (I) or formulations and / or combinations thereof may be carried out before, during and / or after unwanted plant emergence, preferably during and / or after.

[1183] The application of the compound or formulation and / or combination of formula (I) can be carried out before or during sowing.

[1184] Compounds of Formula (I) or formulations and / or combinations thereof may be applied pre-emergence, post-emergence, or before planting, or together with crop seeds. Compounds of Formula (I) or formulations and / or combinations thereof may also be applied by pre-treating crop seeds with compounds of Formula (I) or formulations and / or combinations thereof. If the active ingredient is not well tolerated by certain crops, an application technique (post-guided, final tillage procedure) may be used in which the combination is sprayed with a spraying device to minimize contact with the leaves of sensitive crops, allowing the active ingredient to reach the leaves of unwanted plants growing underneath or the bare soil surface.

[1185] In another embodiment, the compound of formula (I) or formulations and / or combinations thereof may be applied by treating the seeds. Seed treatment generally comprises all procedures well known to those skilled in the art based on the compound of formula (I) or formulations and / or combinations thereof (seed dressing, seed coating, seed dusting, seed soaking, seed coating, multi-layer seed coating, seed hulling, seed dripping, and seed granulation). The combination may be applied diluted or undiluted.

[1186] The term "seed" includes all types of seeds, such as corn, seeds, fruits, tubers, seedlings, and similar forms. The preferred term used here describes corn and its seeds. The seeds used can be from the aforementioned crop plants, but can also be from genetically modified plants or plants obtained through conventional breeding methods.

[1187] When used in plant protection, the amount of active substance without formulation adjuvants, i.e., compound of formula (I), component B and suitable component C, is 0.001-2 kg / ha, preferably 0.005-2 kg / ha, more preferably 0.05-0.9 kg / ha, especially 0.1-0.75 kg / ha, depending on the desired effect.

[1188] In another embodiment of the invention, the application rate of the compound of formula (I), component B and suitable component C is 0.001-3 kg / ha, preferably 0.005-2.5 kg / ha, especially 0.01-2 kg / ha of active substance (as).

[1189] In another preferred embodiment of the invention, the application rate (total amount of compound (I)) of the compound of the present invention depends on the target of control, season, target plant and growth stage and is 0.1-3000 g / ha, preferably 10-1000 g / ha.

[1190] In another preferred embodiment of the invention, the application rate of the compound of formula (I) is 0.1-5000 g / ha, preferably 1-2500 g / ha or 5-2000 g / ha.

[1191] In another preferred embodiment of the invention, the application rate of the compound of formula (I) is 0.1-1000 g / ha, preferably 1-750 g / ha, more preferably 5-500 g / ha.

[1192] The required application rate of herbicide compound B is typically 0.0005-2.5 kg / ha, preferably 0.005-2 kg / ha or 0.01-1.5 kg / ha as.

[1193] The required application rate of safety agent C is typically 0.0005-2.5 kg / ha, preferably 0.005-2 kg / ha or 0.01-1.5 kg / ha as.

[1194] In the treatment of plant propagation materials such as seeds, for example by powdering, coating or soaking the seeds, the required amount of active material is usually 0.1-1000g, preferably 1-1000g, more preferably 1-100g, and most preferably 5-100g / 100kg of plant propagation material (preferably seeds).

[1195] In another embodiment of the invention, in order to treat the seeds, the amount of the active substance, namely the compound of formula (I), component B and suitable component C, applied is typically 0.001-10 kg / 100 kg of seeds.

[1196] When used to protect materials or store products, the amount of active substance applied depends on the type of area to be treated and the desired effect. In material protection, the typical application amount is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active substance per cubic meter of treated material.

[1197] In the case of the combination of the present invention, it is not important whether the compound of formula (I) and other components B and / or components C are formulated and applied together or separately.

[1198] When applied separately, the order in which they are applied is less important. The only requirement is that the compound of formula (I) and other components B and / or C are applied within a timeframe that allows these active ingredients to act on the plant simultaneously, preferably within a timeframe of up to 14 days, and especially up to 7 days.

[1199] Depending on the method of application, compounds of formula (I) or formulations and / or combinations thereof may be used additionally on many other crops to eliminate unwanted plants. Suitable crop examples include: onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), oat (Avena sativa), beet (Beta vulgaris spec.altissima), beet (Beta vulgaris spec.rapa), European rapeseed (Brassica napus var.napus), rutabaga (Brassica napus var.napobrassica), rutabaga (Brassica rapa var.silvestris), kale (Brassica oleracea), black mustard (Brassica nigra), large-leaf tea (Camellia sinensis), safflower (Carthamus tinctorius), American pecan (Carya illinoinensis), lemon (Citrus limon), sweet orange (Citrus sinensis), small-fruit coffee (Coffea arabica) (medium-fruit coffee (Coffea arabica)) The following are genera of plants: canephora, coffee (Coffealiberica), cucumber (Cucumis sativus), bermudagrass (Cynodon dactylon), carrot (Daucus carota), oil palm (Elaeis guineensis), European strawberry (Fragaria vesca), soybean (Glycine max), upland cotton (Gossypium hirsutum) (tree cotton (Gossypium arboreum), grass cotton (Gossypium herbaceum), Gossypium vitifolium), sunflower (Helianthus annuus), Hevea brasiliensis, barley (Hordeum vulgare), hops (Humulus lupulus), sweet potato (Ipomoea batatas), walnut (Juglansregia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersiconlycopersicum), and apple (Malus spec.).), cassava (Manihot esculenta), alfalfa (Medicagosativa), banana (Musa spec.), tobacco (Nicotiana tabacum) (yellow-flowered tobacco (N. rustica)), olive (Olea europaea), rice (Oryza sativa), golden bean (Phaseolus lunatus), common bean (Phaseolus vulgaris), European spruce (Picea abies), pine (Pinus spec.), pistachio (Pistacia vera), Pisumsativum, European sweet cherry (Prunus avium), Prunus persica, pear (Pyrus communis), apricot (Prunus armeniaca), European sour cherry (Prunus cerasus), almond (Prunus dulcis) and European plum (Prunus domestica), Ribes sylvestre, castor bean (Ricinus communis), sugarcane (Saccharum officinarum), rye (Secale cereale), white mustard (Sinapis) The following crops are listed: *Solanum tuberosum*, *Sorghum bicolor* (sorghum vulgare), *Theobromacacao*, *Trifolium pratense*, *Triticum aestivum*, *Triticale*, *Triticum durum*, broad bean (*Vicia faba*), grape (*Vitis vinifera*), and maize (*Zea mays*).

[1200] Preferred crops include peanut (Arachis hypogaea), sugar beet (Beta vulgarisspec.altissima), European rapeseed (Brassica napus var.napus), kale (Brassica oleracea), lemon (Citrus limon), sweet orange (Citrus sinensis), small-fruited coffee (Coffea arabica) (medium-fruited coffee (Coffea canephora), large-fruited coffee (Coffea liberica)), bermudagrass (Cynodon dactylon), soybean (Glycine max), upland cotton (Gossypium hirsutum) (tree cotton (Gossypium arcoreum), herb cotton (Gossypium herbaceum), Gossypium vitifolium), sunflower (Helianthus annuus), barley (Hordeum vulgare), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), and tomato (Lycopersicon). lycopersicum), Malus spec., Alfalfa (Medicago sativa), Tobacco (Nicotiana tabacum) (Yellow-flowered Tobacco (N. rustica)), Olive (Olea europaea), Rice (Oryza sativa), Golden Bean (Phaseolus lunatus), Common Bean (Phaseolus vulgaris), Pistachio (Pistacia vera), Pisum sativum, Almond (Prunus dulcis), Sugarcane (Saccharum officinarum), Rye (Secale cereale), Potato (Solanum tuberosum), Bicolor Sorghum (Sorghum vulgare) (Triticale), Common Wheat (Triticumaestivum), Durum Wheat (Triticum durum), Broad Bean (Vicia faba), Grape (Vitis vinifera), and Maize (Zea mays).

[1201] The preferred crops are cereal crops, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts, or perennial crops.

[1202] The compounds of formula (I) of the present invention, or formulations and / or combinations thereof, can also be used in crops that have been modified by mutagenesis or genetic engineering to provide new traits to plants or to modify existing traits.

[1203] The term “crop” as used in this article also includes plants (agricultural crops) that have been modified by mutagenesis or genetic engineering to provide new traits or modify existing traits.

[1204] Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, but there are also targeted mutagenesis techniques to induce mutations at specific locations in the plant genome. Targeted mutagenesis techniques typically use oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs, or a wide range of nucleases to achieve a targeted effect.

[1205] Genetic engineering typically uses recombinant DNA techniques, which are not easily obtained naturally through hybridization, mutagenesis, or natural recombination, to produce modifications in the plant genome. One or more genes are usually integrated into the plant genome to add or improve traits. These integrated genes are also known in the field as transgenes, and plants containing such transgenes are called transgenic plants. This plant conversion method usually produces several conversion events, which differ in the genomic location where the transgene has been integrated. Plants containing a specific transgene at a specific genomic location are often described as containing a specific "event," which is referred to by the event name. Traits that have been introduced into plants or modified include herbicide tolerance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought.

[1206] Herbicide tolerance has been developed through mutagenesis and genetic engineering. Plants conferred tolerance to acetolactate synthase (ALS) inhibitor herbicides by conventional mutagenesis and breeding methods include those named after herbicides such as... Commercially available plant varieties. However, most herbicide tolerance traits have been developed through the use of genetic modification.

[1207] The herbicides glyphosate, glufosinate, 2,4-D, dicamba, oxynil (such as bromoxynil and ioxynil), sulfonylurea herbicides, ALS inhibitor herbicides, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors such as isopropionate have been tested. Isoxaflutole and mesotrione develop herbicide tolerance.

[1208] Transgenic herbicides already used to provide herbicide tolerance traits include: glyphosate tolerance: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; glufosinate tolerance: pat and bar; 2,4-D tolerance: aad-1 and aad-12; dicamba tolerance: dmo; oxynil herbicide tolerance: bxn; sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA; ALS inhibitor herbicide tolerance: csr1-2; HPPD inhibitor herbicide tolerance: hppdPF, W336, and avhppd-03.

[1209] Transgenic maize varieties containing herbicide tolerance genes include, for example, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, and HCEM485. 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275, but others are not excluded.

[1210] Transgenic soybeans containing herbicide tolerance genes include, for example, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, and GU262. W62, W98, FG72, and CV127, but others are not excluded.

[1211] Transgenic cotton events containing herbicide tolerance genes include, for example, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40, but others are not excluded.

[1212] Transgenic Carola events containing herbicide tolerance genes include, for example, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3, but others are not excluded.

[1213] Insect resistance is primarily developed by transferring bacterial genes encoding insecticidal proteins into plants. The most commonly used transgenes are toxin genes from the genus *Bacillus* spp. and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, cry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20. However, plant-derived genes, particularly those encoding protease inhibitors such as CpTI and pinII, are also transferred into other plants. Another approach uses transgenes to target and downregulate insect genes by producing double-stranded RNA in plants. An example of such a transgene is dvsnf7.

[1214] Transgenic maize events containing insecticidal protein genes or double-stranded RNA include, for example, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098, but others are not excluded.

[1215] Genetically modified soybeans containing insecticidal protein genes include, for example, MON87701, MON87751 and DAS-81419, but others cannot be ruled out.

[1216] Transgenic cotton events containing insecticidal protein genes include, for example, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119, and SGK321, but others are not excluded.

[1217] Increased yields are achieved by using, for example, the transgenic athb17 present in maize event MON87403 to increase ear biomass or by using, for example, the transgenic bbx32 present in soybean event MON87712 to increase photosynthesis.

[1218] Crops containing modified oil content have been produced using transgenic genes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A. Soybean events containing at least one of these genes are: 260-05, MON87705, and MON87769.

[1219] Tolerance to abiotic conditions, especially drought tolerance, was improved through the use of transgenic cspB contained in the maize event MON87460 and through the use of the soybean event. The included transgenic Hahb-4 is produced.

[1220] Traits are typically combined by combining genes during conversion events or by combining different events during the breeding process. Preferred combinations of traits include herbicide tolerance to different classes of herbicides, insect tolerance to different insect species, especially tolerance to Lepidoptera and Coleoptera, herbicide tolerance combined with resistance to one or more insect species, herbicide tolerance combined with increased yield, and herbicide tolerance combined with tolerance to abiotic conditions.

[1221] Plants containing individual or stacked traits, as well as the genes and events that provide these traits, are well known in the art. For example, detailed information about mutagenic or integrated genes and corresponding events can be obtained from the websites of organizations such as the International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Center for Environmental Risk Assessment (CERA) (http: / / cera-gmc.org / GMCropDatabase), as well as patent applications such as EP 3028573 and WO2017 / 011288.

[1222] The use of compounds of formula (I) of the present invention, or formulations and / or combinations thereof, on crops may result in effects specific to crops containing certain genes or events. These effects may involve changes in growth behavior or tolerance to biotic or abiotic stressors. Such effects may in particular include increased yield, increased resistance or tolerance to insect, nematode, fungal, bacterial, mycoplasma, viral, or viroid pathogens, as well as changes in early vigor, early or delayed maturity, cold or heat tolerance, and amino acid or fatty acid profiles or contents.

[1223] In addition, this includes plants that contain altered or new amounts of components through the use of recombinant DNA technology to particularly improve the production of raw materials, such as potatoes that produce increased amounts of amylopectin (e.g., potatoes). Potatoes (BASF SE, Germany).

[1224] Furthermore, compounds of formula (I) of the present invention, or formulations and / or combinations thereof, have been found to be suitable for defoliation and / or drying of plant parts of crops such as cotton, potatoes, rapeseed, sunflower, soybean, or broad beans, especially cotton. In this regard, formulations and / or combinations for crop drying and / or defoliation, methods for preparing these formulations and / or combinations, and methods for drying and / or defoliating plants using compounds of formula (I) have been discovered.

[1225] As a desiccant, the compound of formula (I) is particularly suitable for drying crops such as potatoes, rapeseed, sunflowers, and soybeans, as well as the above-ground parts of cereals. This makes fully mechanized harvesting of these important crops possible.

[1226] Also of economic significance is the promotion of harvesting citrus fruits, olives, and other pome, drupe, and nut fruits of various species and varieties, which is made possible by concentrated splitting or reduced adhesion to the tree within a certain timeframe. The same mechanism, namely promoting the formation of detachment tissue between the fruit or leaf portion and the branch portion of the plant, is also necessary for the controlled defoliation of useful plants, especially cotton.

[1227] In addition, the shortened time interval between the maturity of each cotton plant leads to improved fiber quality after harvest. Example

[1228] A Chemical Example

[1229] Chemical bonds drawn as bars in a chemical formula represent relative stereochemistry in a ring system.

[1230] Example 1: Synthesis of 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylic acid (Inter A)

[1231] An aqueous solution of lithium hydroxide (118 mg, 4.95 mmol) was added dropwise to a mixture of 2,2-diethoxyoxetane-2,2-dicarboxylic acid (1) (CAS [1384465-73-9]) (1000 mg, 4.95 mmol), tetrahydrofuran (THF) (50 mL), and water (50 mL), and the reaction mixture was stirred overnight at room temperature. The THF was evaporated under vacuum, and the residue was washed with methyl tert-butyl ether. The aqueous solution was concentrated under vacuum, and the residue was dried to give product (2) (740 mg, 86% yield). ¹H NMR (500 MHz, deuterium oxide) δ 4.55 (t, 2H), 4.28 (m, 2H), 3.13 (m, 1H), 2.91 (m, 1H), 1.29 (t, 3H).

[1232]

[1233] Aniline 3 (3.17 g, 19.6 mmol) was added to a solution of ethyl 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylate (2) (3.52 g, 19.6 mmol) in dimethylformamide (DMF). HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethylurea hexafluorophosphate, CAS [148893-10-1]) (8.18 g, 21.5 mmol) was added to the resulting solution, followed by diisopropylethylamine (16.6 mL). The resulting reaction mixture was stirred overnight at room temperature. Water and sodium bicarbonate solution were added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give ethyl 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylate (4) (1.6 g, 26%). ¹H NMR (500 MHz, chloroform-d) δ 8.71 (s, 1H), 7.61 (d, 2H), 7.16 (d, 1H), 4.74 (dt, 1H), 4.66 (m, 1H), 4.31 (q, 2H), 3.42 (ddd, 1H), 2.95 (ddd, 1H), 1.32 (t, 3H).

[1234]

[1235] An aqueous solution of lithium hydroxide (23 mg, 3.8 mmol) was added dropwise to a mixture of ethyl 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylate (4) (150 mg, 0.472 mmol), tetrahydrofuran (THF) (10 mL), and water (10 mL), and the reaction mixture was stirred overnight at room temperature. The THF was evaporated under vacuum, and the residue was washed with methyl tert-butyl ether (MTBE). The aqueous solution was concentrated under vacuum, and the residue was dried to give carboxylic acid Inter A (130 mg, 95% yield). ¹H NMR (500 MHz, methanol-d⁴) δ 7.76 (d, 2H), 7.21 (t, 1H), 6.56 (m, 1H), 4.67 (t, 2H), 3.31 (m, 1H), 2.94 (dt, 1H).

[1236] Example 2:

[1237] Synthesis of (1S,4R)-4-[[2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester (a 1:1 mixture of diastereomers) – Compound I.6

[1238]

[1239] To a solution of carboxylic acid Inter A (330 mg, 1.14 mmol) in dimethylformamide (DMF), methyl (1S,4R)-4-aminocyclopentan-2-ene-1-carboxylate hydrochloride (7, CAS [180196-56-9]) (202 mg, 1.14 mmol) was added. To the resulting solution, HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethylurea hexafluorophosphate, CAS [148893-10-1]) (476 mg, 1.25 mmol) was added, followed by diisopropylethylamine (0.76 mL). The resulting reaction mixture was stirred overnight at room temperature. Water and sodium bicarbonate solution were added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give compound I.6 (62 mg, 13%, a 1:1 mixture of diastereomers). ¹H NMR (400 MHz, chloroform-d) δ 9.37 (s, 1H), 9.25 (s, 1H), 7.59 (m, 4H), 7.12 (m, 2H), 5.94 (m, 4H), 5.08 (m, 2H), 4.73 (m, 4H), 3.74 (s, 3H), 3.73 (s, 3H), 3.56 (m, 2H), 3.05 (m, 4H), 2.51 (m, 2H), 2.05 (dt, 1H), 1.95 (dt, 1H).

[1240] Example 3:

[1241] Synthesis of (3S)-3-[[2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carbonyl]amino]methyl butyrate (a 1:1 mixture of diastereomers) – Compound I.7

[1242]

[1243] To a solution of carboxylic acid Inter A (130 mg, 0.448 mmol) in dimethylformamide (DMF, 5 mL), (3S)-3-aminobutyrate (S-homoalanine) hydrochloride (89 mg, 0.081 mmol) (CAS [139243-55-3]) was added. To the resulting solution, HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethylurea hexafluorophosphate, CAS [148893-10-1]) (187 mg, 0.493 mmol), followed by triethylamine (0.22 mL) was added. The resulting reaction mixture was stirred overnight at room temperature. Water and sodium bicarbonate solution were added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as a solvent to give compound I.7 (102 mg, 58%, a 1:1 mixture of diastereomers). ¹H NMR (400 MHz, chloroform-d) δ 9.68 (s, ¹H), 9.48 (s, ¹H), 7.76 (m, 6H), 7.15 (m, 2H), 4.57 (m, 5H), 4.32 (dqd, 2H), 3.62 (s, 3H), 3.58 (s, 3H), 2.97 (m, 4H), 2.55 (m, 4H), 1.24 (d, 3H), 1.21 (d, 3H).

[1244] Example 4:

[1245] Synthesis of (1S,4R)-4-[[2-[(3,5-difluorophenyl)carbamoyl]oxetane-2-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester (a 1:1 mixture of diastereomers) – Compound I.1

[1246] Inter B was obtained as a grayish-white solid by saponification of 1-(3,5-fluorophenyl)-3-methyl-2-oxo-azacyclobutane-3-carboxylate, similar to the synthesis of Inter A starting from 2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carboxylate.

[1247]

[1248] To a solution of carboxylic acid Inter B (130 mg, 0.506 mmol) in dimethylformamide (DMF), methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate (5, CAS [229613-83-6]) (99 mg, 0.56 mmol) was added. To the resulting solution, HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethylurea hexafluorophosphate, CAS [148893-10-1]) (0.21 g, 0.56 mmol) was added, followed by diisopropylethylamine (2.5 mL). The resulting reaction mixture was stirred overnight at room temperature. Water and sodium bicarbonate solution were added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give compound I.1 (105 mg, 56%, a 1:1 mixture of diastereomers). ¹H NMR: (400 MHz, chloroform-d) δ 9.39 (s, 1H), 9.28 (s, 1H), 7.58 (s, 2H), 7.23 (d, 4H), 6.58 (t, 2H), 5.99 (d, 2H), 5.08 (s, 2H), 4.75 (m, 3H), 3.74 (s, 3H), 3.73 (s, 3H), 3.57 (m, 2H), 3.04 (dd, 3H), 2.50 (m, 2H), 2.05 (d, 1H), 1.95 (d, 1H).

[1249] Example 5:

[1250] Synthesis of (3S)-3-[[2-[(3,5-difluorophenyl)carbamoyl]oxetane-2-carbonyl]amino]methyl butyrate (a 1:1 mixture of diastereomers) – compound I.2.

[1251]

[1252] To a solution of carboxylic acid Inter B (19 mg, 0.074 mmol) in dimethylformamide (DMF), (3S)-3-aminobutyrate (S-homoalanine) hydrochloride (12 mg, 0.081 mmol) (CAS [139243-55-3]) was added. To the resulting solution, HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethylurea hexafluorophosphate, CAS [148893-10-1]) (31 mg, 0.081 mmol), followed by diisopropylethylamine (0.22 mL) was added. The resulting reaction mixture was stirred overnight at room temperature. Water and sodium bicarbonate solution were added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as a solvent to give compound I.2 (17 mg, 65%, a 1:1 mixture of diastereomers). 1H NMR(400MHz,THF-d8)δ9.72(s,1H),9.52(s,1H),7.75(m,2H),7.40(m,4H),6.67(m,2H),4. 56(m,3H),4.31(dq,1H),3.58(m,6H),2.98(m,2H),2.51(m,4H),1.25(d,3H),1.21(d,3H).

[1253] Example 6:

[1254] Synthesis of 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid (Inter C)

[1255]

[1256] 4-Acetaminobenzenesulfonyl azide (2) (p-ABSA, 12 g, 465 mmol) (CAS [53051-81-3]) was added to a mixture of diethyl malonate (1) (50 g, 310 mmol) (CAS [53051-81-3]) and triethylamine (75 g, 744 mmol) in MeCN (500 mL) at 20 °C. The mixture was stirred at 20 °C for 16 h. The reaction mixture was filtered and the filtrate was concentrated. Dichloromethane (100 mL) was added to the filtrate. The mixture was filtered and the filtrate was concentrated. The crude product was purified by HPLC (EtOAc / PE = 0%–100%) to give diethyl 2-diazomalonate (2) (62 g, quantitative), as a yellow oil. ¹H NMR (400 MHz, chloroform-d) δ 4.31 (q, 4H), 1.32 (t, 6H).

[1257]

[1258] Rh2(OAc)4 (1.3 g, 2.9 mmol) (CAS [15956-28-2]) was added to a solution of diethyl 2-diazomalonate (3) (62 g, 330 mmol) and propargyl alcohol (4) (18.5 g, 330 mmol) (CAS [107-19-7]) in toluene (600 ml) at 20 °C. The mixture was stirred at 60 °C for 1 h. The reaction was filtered and the filtrate was concentrated. The crude product was purified by HPLC (EtOAc / PE = 0%–100%) to give diethyl 2-prop-2-alkynoxymalonate (5) (53 g, two-step yield 80%) as a yellow oil. ¹H NMR (400 MHz, chloroform-d) δ 4.82–4.80 (s, ¹H), 4.41 (d, 2H), 4.28 (m, 4H), 2.53 (t, ¹H), 1.31 (t, 6H).

[1259]

[1260] KOH (7.85 g, 140 mmol) was added in portions to a solution of diethyl 2-propane-2-alkynyloxymalonic acid (5) (30 g, 140 mmol) in EtOH / H2O (200 / 200 mL) at 20 °C. The mixture was stirred at 20 °C for 16 h. The mixture was quenched with water and adjusted to pH 3 with 6 N HCl, and extracted with EtOAc. The combined organic matter was washed with brine, dried and concentrated to give 2-ethoxycarbonylhydrofuran-2-carboxylic acid (6) (20 g, 77%) as a yellow oil. ¹H NMR (400 MHz, chloroform-d) δ 6.23 (m, 1H), 6.02 (tdd, 1H), 4.93 (m, 1H), 4.87 (m, 1H), 4.29 (q, 2H), 1.32 (t, 3H).

[1261]

[1262] Similar to the synthesis of Inter A described above, ethyl 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylate (8) was obtained from 2-ethoxycarbonylhydrofuran-2-carboxylic acid (20 g, 108 mmol) as a yellow solid (23 g, 66%). ¹H NMR (400 MHz, chloroform-d) δ 8.32 (br s, 1H), 7.56 (d, J = 1.8 Hz, 2H), 7.14 (m, 1H), 6.20 (m, 1H), 6.01 (m, 1H), 4.89–4.86 (m, 1H), 4.81 (s, 1H), 4.28 (m, 4H), 1.32 (t, 3H).

[1263]

[1264] KOH (452 ​​mg, 8.06 mmol) was added in portions to a solution of ethyl 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid (8) (1.33 g, 4.03 mmol) in EtOH / H2O (40 / 20 mL) at 20 °C. The mixture was stirred at 20 °C for 16 h. The mixture was quenched with water and adjusted to pH 3 with 6N HCl, and extracted with EtOAc. The combined organic matter was washed with brine, dried, and concentrated to give 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid Inter C (950 mg, 78%) as a yellow oil. ¹H NMR (400 MHz, chloroform-d) δ 6.23 (m, ¹H), 6.02 (tdd, ¹H), 4.93 (m, ¹H), 4.87 (m, ¹H), 4.29 (q, 2H), 1.32 (t, 3H).

[1265] Example 7:

[1266] Synthesis of (1S,4R)-4-[[5-[(3,5-dichlorophenyl)carbamoyl]-2H-furan-5-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester (a 1:1 mixture of diastereomers) – Compound I.24

[1267]

[1268] Similar to the synthesis of compound I.6 above, compound I.24 was obtained from 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid (Inter C) (48 mg, 0.16 mmol), as a grayish-white solid (49 mg, 73%, a 1:1 mixture of diastereomers). ¹H NMR (400 MHz, chloroform-d) δ 9.60 (s, 1H), 9.51 (s, 1H), 7.56 (m, 6H), 7.09 (m, 2H), 6.13 (m, 2H), 6.07 (m, 2H), 5.96 (m, 2H), 5.88 (m, 2H), 5.02 (m, 6H), 3.74 (m, 3H), 3.73 (s, 3H), 3.54 (m, 2H), 2.47 (dtd, 2H), 1.93 (m, 2H).

[1269] Two diastereomers were transduced by SFC (column: (S,S)-WHELK-O1, 50x6mm iD, 3.5μm; mobile phase A: CO2; mobile phase B: IPA (0.1% IPAm, v / v; flow rate: 3.4 mL / min, column temperature: 35℃, ABPR: 1800 psi; gradient: time (A / B): 0.0 (95 / 5), 0.2 min (95 / 5), 1.2 min (50 / 50), 2.2 (50 / 50), 2.6 min (95 / 5), 3.0 (95 / 5)). They are described as compounds I.183 and I.184 in Table 2 below. Their characterization is as follows:

[1270] Compound I.183:t R =1.395 min, 1H NMR (400 MHz, chloroform-d) δ 9.52 (s, 1H), 7.56 (m, 3H), 6.13 (m, 1H), 6.07 (m, 1H), 5.96 (m, 1H), 5.88 (m, 1H), 5.02 (m, 3H), 3.75 (s, 3H), 3.55 (m 1H), 2.47 (dtd, 1H), 1.93 (m, 2H).

[1271] Compound I.184:t R =1.616 min, 1H NMR (400 MHz, chloroform-d) δ 9.63 (s, 1H), 7.56 (m, 3H), 6.13 (m, 1H), 6.07 (m, 1H), 5.96 (m, 1H), 5.88 (m, 1H), 5.02 (m, 3H), 3.74 (s, 3H), 3.55 (m 1H), 2.47 (dtd, 1H), 1.93 (m, 2H).

[1272] Example 8:

[1273] Synthesis of 5-[(3,5-dichlorophenyl)carbamoyl]-1,3-dimethylhydrofuran-5-carboxylic acid (a 1:1 mixture of diastereomers) – Inter D

[1274]

[1275] To a solution of diethyl 2-diazomalonate (1) (1.13 g, 6.07 mmol) in toluene (25 mL), pent-3-yn-2-ol (0.85 mL, 9.1 mmol) was added. [Rh(OAc)₂]₂ (0.12 g, 0.30 mmol) was added to the resulting solution, and the reaction mixture was stirred at 60 °C for 2 h. After cooling to room temperature, the reaction mixture was washed with water, dried (sodium sulfate), and the solvent was evaporated under reduced pressure. Crude product 2 (1.10 g, 75%) was ready for the next step without further purification. ¹H NMR (400 MHz, chloroform-d, 1:1 mixture of diastereomers): δ 4.39 (m, 1H), 4.26 (m, 4H), 1.82 (d, 3H), 1.47 (d, 3H), 1.28 (m, 6H).

[1276]

[1277] Cesium carbonate (2.96 g, 9.08 mmol) was added to a solution of diethyl 2-propane-2-alkynoxymalonate (2) (1.10 g, 4.54 mmol) in acetonitrile (50 mL). The resulting reaction mixture was stirred at room temperature for 4 h. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate and water. The organic layer was separated, washed with water (2x), dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give 3 (1.00 g, 59%, a 1:1 mixture of diastereomers). ¹H NMR (400 MHz, chloroform-d, a 1:1 mixture of diastereomers) δ 5.71 (t, 1H), 5.07 (dtt, 1H), 4.25 (m, 4H), 1.90 (m, 3H), 1.29 (m, 9H).

[1278]

[1279] Similar to the synthesis of Inter A described above, 2-ethoxycarbonyl-3,5-dimethylfuran-2,2-dicarboxylic acid (4) was obtained from diethyl 3,5-dimethylfuran-2,2-dicarboxylic acid (750 mg, 3.1 mmol) as an oil (580 mg, 87%, a 1:1 mixture of diastereomers). ¹H NMR (400 MHz, chloroform-d) δ 5.71 (t, 1H), 5.07 (dtt, 1H), 4.25 (m, 2H), 1.90 (t, 3H), 1.29 (m, 6H).

[1280]

[1281] Similar to the synthesis of Inter A described above, ethyl 5-[(3,5-dichlorophenyl)carbamoyl]-1,3-dimethylhydrofuran-5-carboxylic acid (305 mg, 1.42 mmol) was obtained as a yellow solid (250 mg, 49%), starting from 2-ethoxycarbonyl-3,5-dimethylhydrofuran-2-carboxylic acid. ¹H NMR (400 MHz, chloroform-d) δ 8.69 (s, 1H), 7.56 (d, 2H), 7.12 (m, 1H), 5.71 (m, 1H), 4.27 (m, 2H), 1.34 (d, 3H), 1.30 (t, 3H). ¹H NMR (400 MHz, chloroform-d, minor diastereomer) δ = 8.69 (s, ¹H), 7.53 (d, 2H), 7.12 (m, ¹H), 5.71 (m, ¹H), 4.27 (m, 2H), 1.45 (d, 3H), 1.30 (t, 3H).

[1282]

[1283] Similar to the synthesis of Inter A described above, 5-[(3,5-dichlorophenyl)carbamoyl]-1,3-dimethylhydrofuran-5-carboxylic acid ethyl ester (250 g, 0.70 mmol) was used to obtain 5-[(3,5-dichlorophenyl)carbamoyl]-1,3-dimethylhydrofuran-5-carboxylic acid (Inter D), a white solid (128 mg, 56%, a 1:3 mixture of diastereomers). ¹H NMR (400 MHz, chloroform-d, major diastereomer) δ = 8.84 (s, 1H), 7.53 (d, 2H), 7.19 (t, 1H), 5.75 (dt, 1H), 5.29 (dtd, 1H), 1.97 (t, 3H), 1.51 (dd, 3H). ¹H NMR (400 MHz, chloroform-d, minor diastereomer) δ = 8.84 (s, ¹H), 7.50 (d, 2H), 7.21 (t, ¹H), 5.75 (dt, ¹H), 5.40 (dt, ¹H), 1.95 (t, 3H), 1.51 (dd, 3H).

[1284] Example 9:

[1285] Synthesis of (1S,4R)-4-[[5-[(3,5-dichlorophenyl)carbamoyl]-2,4-dimethyl-2H-furan-5-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester (a 1:2:3 mixture of diastereomers) – Compound I.29

[1286]

[1287] In a manner similar to the synthesis of compound I.6 above, starting with 5-[(3,5-dichlorophenyl)carbamoyl]-1,3-dimethylhydrofuran-5-carboxylic acid (Inter D) (58 mg, 0.17 mmol), compound I.29 was obtained as a grayish-white solid (65 mg, 82%, a 1:2:3 mixture of diastereomers). 1H NMR (400MHz, chloroform-d) δ9.84(m,1H),7.66(m,1H),7.57(m,2H),7.10(m,1H),5.96(m,1H),5.87(m,1H),5. 64(m,1H),5.30(m,1H),5.03(m,1H),3.73(m,3H),3.54(m,1H),2.49(m,1H),1.93(m,4H),1.46(m,3H).

[1288] Example 10:

[1289] Synthesis of (4S)-4-[[5-[(3,5-dichlorophenyl)carbamoyl]-2,4-dimethyl-2H-furan-5-carbonyl]amino]valerate methyl ester (a mixture of diastereomers in a 1:1:1:1 mixture) – Compound I.30

[1290]

[1291] In a manner similar to the synthesis of compound I.6 above, starting from 5-[(3,5-dichlorophenyl)carbamoyl]-hydrofuran-5-carboxylic acid (Inter D) (50 mg, 0.15 mmol), compound I.30 was obtained as a grayish-white solid (60 mg, 89%, a 1:1:1:1 mixture of diastereomers). 1H NMR (400MHz, chloroform-d) δ9.99(s,1H),9.92(s,1H),9.87(s,1H),9.80(s,1H),7.56(m,8H),7.15(m,4H),7.10(m,4H),5.64(m,4H),5.30 (m,4H),3.99(m,4H),3.67(m,12H),2.33(m,8H),1.93(m,12H),1.86(m,4H),1.78(m,4H),1.50(m,6H),1.43(t,6H),1.19(m,12H).

[1292] Example 11:

[1293] Synthesis of [(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carboxylic acid (Inter E)

[1294]

[1295] H₂SO₄ (0.2 ml) was added to a mixture of tetrahydrofuran-2-carboxylic acid (1) (5 g, 43 mmol) in MeOH (15 ml) at 25 °C and stirred at 75 °C for 16 h. The mixture was poured into H₂O and extracted with dichloromethane. The combined organic matter was washed with aqueous NaHCO₃, dried, and concentrated. The crude product was purified by distillation to give methyltetrahydrofuran-2-carboxylic acid (2) (3.5 g, 62.5%) as a yellow oil. ¹H NMR (400 MHz, chloroform-d) δ 4.48 (m, 1H), 3.97 (m, 2H), 3.74 (s, 3H), 2.28 (m, 2H), 2.10 (m, 1H), 1.96 (m, 1H).

[1296]

[1297] Diisopropylaminolithium (LDA) (17 ml, 34.5 mmol) was added dropwise to a mixture of methyltetrahydrofuran-2-carboxylic acid (2) (3 g, 23 mmol) in THF (50 ml) at -78 °C. The mixture was stirred at -78 °C for 0.5 h, and then benzyl chloroformate (3) (15.7 g, 92 mmol) was added. The mixture was stirred at -78 °C to 20 °C for 1 h. The mixture was poured into H2O, the pH was adjusted to 3, and the mixture was extracted with EtOAc. The combined organic matter was washed with brine, dried, and concentrated. The crude product was purified by column chromatography using ethyl acetate and hexane to give benzyl methyl tetrahydrofuran-2,2-dicarboxylic acid (4) (2.5 g, 33%) as a yellow oil. ¹H NMR (400 MHz, chloroform-d) δ 7.35 (m, 5H), 5.24 (d, 2H), 4.07 (t, 2H), 3.75 (s, 3H). 2.46(m,2H), 2.01(m,2H).

[1298]

[1299] A solution of benzyl methyl tetrahydrofuran-2,2-dicarboxylate (4) (2.2 g, 8.33 mmol) in MeOH (200 ml) was added to a mixture of Pd / C (200 mg), and the mixture was stirred at 25 °C under H2 (50 psi) for 2 h. The mixture was filtered and concentrated to give compound 2-methoxycarbonyltetrahydrofuran-2-carboxylic acid (5) (1.4 g, 97%) as a yellow oil. ¹H NMR (400 MHz, chloroform-d) δ 4.12 (quin, 2H), 3.82 (s, 3H), 2.47 (m, 2H), 2.05 (m, 3H).

[1300]

[1301] 3,5-Dichloroaniline (6) (1.4 g, 8.6 mmol) and HATU (2.6 g, 6.9 mmol) were added to a mixture of carboxylic acid 5 (1 g, 5.75 mmol) in DMF (20 mL) at 15 °C and stirred at 15 °C for 24 h. The mixture was poured into ice water and extracted with methyl tert-butyl ether. The combined organic matter was washed with brine, dried, and concentrated. The crude product was purified by preparative HPLC (TFA-ACN-H2O) to give methyl 2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carboxylate (7) (900 mg, 49%) as a white solid. ¹H NMR (400 MHz, chloroform-d) δ 8.61 (br s, ¹H), 7.58 (d, 2H), 7.14 (t, ¹H), 4.12 (m, 2H), 3.81 (s, 3H), 2.75 (td, ¹H), 2.44 (ddd, ¹H), 2.11 (m, ¹H), 1.99 (m, ¹H).

[1302]

[1303] An aqueous solution of lithium hydroxide (133 mg, 5.56 mmol) was added dropwise to a mixture of methyl 2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carboxylate (7) (885 mg, 2.78 mmol), tetrahydrofuran (THF) (50 mL), and water (50 mL), and the reaction mixture was stirred overnight at room temperature. The THF was evaporated under vacuum, and the residue was washed with methyl tert-butyl ether. The aqueous solution was concentrated under vacuum, and the residue was dried to give [(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carboxylic acid (Inter E) (750 mg, 89% yield). 1H NMR: (400MHz, chloroform-d) δ 8.77 (s, 1H), 7.55 (d, 2H), 7.18 (t, 1H), 4.29 (tq, 2H), 2.63 (ddd, 1H), 2.46 (ddd, 1H), 2.16 (tt, 1H), 2.05 (m, 1H).

[1304] Example 12:

[1305] Synthesis of (1S,4R)-4-[[2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester (a 1:1 mixture of diastereomers) – Compound I.16

[1306] In a similar manner to the synthesis of methyl (1S,4R)-4-[[2-[(3,5-dichlorophenyl)carbamoyl]oxetane-2-carbonyl]amino]cyclopent-2-ene-1-carboxylate (compound I.6) starting from Inter A, Inter E was converted to compound I.16.

[1307]

[1308] To a solution of [(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carboxylic acid (Inter E) (100 mg, 0.329 mmol) in dimethylformamide (DMF), methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate (5, CAS [229613-83-6]) (76 mg, 0.43 mmol) was added. To the resulting solution, HATU (2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethylurea hexafluorophosphate, CAS [148893-10-1]) (162 mg, 0.427 mmol) was added, followed by diisopropylethylamine (0.17 mL). The resulting reaction mixture was stirred overnight at room temperature. Water and sodium bicarbonate solution were added to the reaction mixture. The reaction mixture was extracted with ethyl acetate, washed with water, dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent to give compound I.16 (119 mg, 85%, a 1:1 mixture of diastereomers). ¹H NMR: (400 MHz, chloroform-d) δ 9.71 (s, 1H), 9.66 (s, 1H), 7.73 (m, 4H), 7.54 (m, 2H), 7.11 (m, 2H), 5.90 (dq, 2H), 5.81 (tq, 2H), 4.95 (m, 2H), 4.08 (m, 4H), 3.65 (s, 3H), 3.65 (s, 3H), 3.50 (m, 2H), 2.45 (m, 5H), 2.35 (m, 1H), 1.90 (m, 5H), 1.84 (dd, 1H).

[1309] Example 13:

[1310] Synthesis of (1S,4R)-4-[[2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]cyclopentane-1-carboxylate (a 1:1 mixture of diastereomers) – Compound I.15

[1311] Inter E was converted to compound I.15 in a manner similar to that used in the synthesis of methyl (1S,4R)-4-[[2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]cyclopent-2-ene-1-carboxylate (compound I.16).

[1312]

[1313] [(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carboxylic acid Inter E (100 mg, 0.329 mmol) was treated with (1S,4R)-4-aminocyclopentane-1-carboxylic acid hydrochloride (CAS [222530-29-2]) (84 mg, 0.43 mmol) to give (1S,4R)-4-[[2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]cyclopentane-1-carboxylic acid (compound I.15), as a colorless oil (82 mg, 58%, a 1:1 mixture of diastereomers). 1H NMR: (400MHz, chloroform-d)δ9.75(s,1H),9.69(s,1H),7.71(d,2H),7.70(d,2H),7.55(m,2H),7.12(t,2H),4.23(m,3H),4. 09(m,5H),3.62(s,4H),3.62(s,3H),2.86(m,2H),2.38(m,6H),2.14(m,2H),1.90(m,7H),1.72(m,1H),1.62(m,1H).

[1314] Example 14:

[1315] Synthesis of methyl 4-[[2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]butyrate – Compound I.18

[1316] Inter E was converted to compound I.18 in a manner similar to that used in the synthesis of methyl (1S,4R)-4-[[2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]cyclopent-2-ene-1-carboxylate (compound I.16).

[1317]

[1318] Treatment of [(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carboxylic acid (In-terE) (100 mg, 0.329 mmol) with methyl 3-aminopropionate yielded 4-[[2-[(3,5)methyl ester-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]butyrate (compound I.18), as a colorless oil (96 mg, 72%). ¹H NMR: (400MHz, chloroform-d) δ 9.43 (s, ¹H), 7.55 (d, 2H), 7.24 (m, ¹H), 7.10 (t, ¹H), 4.23 (dp, 2H), 3.68 (s, 3H), 3.34 (tt, 2H), 2.47 (m, 1H), 2.44 (m, 1H), 2.36 (t, 2H), 2.04 (dt, 1H), 1.98 (m, 1H), 1.87 (m, 2H).

[1319] Example 15:

[1320] Synthesis of (3S)-3-[[2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]butyrate (a 1:1 mixture of diastereomers) – Compound I.17

[1321] Inter E was converted to compound I.17 in a manner similar to that used in the synthesis of (1S,4R)-4-[[2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]cyclopent-2-ene-1-carboxylic acid methyl ester compound I.16.

[1322]

[1323] [(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carboxylic acid Inter E (100 mg, 0.329 mmol) was treated with (3S)-aminobutyrate methyl hydrochloride to give (3S)-3-[[2-[(3,5-dichlorophenyl)carbamoyl]tetrahydrofuran-2-carbonyl]amino]butyrate methyl ester (compound I.17), as a colorless oil (120 mg, 90%, a 1:1 mixture of diastereomers). 1H NMR: (400MHz, chloroform-d) δ 9.48 (s, 1H), 9.28 (s, 1H), 7.58 (d, 2H), 7.56 (d, 2H), 7.48 (m, 2H), 7.08 (m, 2H), 4.33 (qd, 2H), 4.20 (tdd, 4H), 3.69 (s, 3H), 3.67 (s, 3H), 2.50 (m, 8H), 2.00 (m, 4H), 1.26 (m, 6H).

[1324] Example 16:

[1325] 2-[(3,5-dichlorophenyl)carbamoyl]-1,3-oxothiacyclopentane-2-carboxylic acid (Inter F)

[1326]

[1327] Sodium hydride (26 g, 0.65 mol) was added to a mixture of 2-hydroxyethanol (2) (23.4 g, 0.3 mol) in THF (2 L) at 20 °C and stirred for 2 h. Then, it was added dropwise to a solution of diethyl dibromomalonate (1) (75.4 g, 0.3 mol) in THF (100 mL) and maintained at 20 °C for 4 h. The mixture was stirred at 20 °C under nitrogen for 16 h. The mixture was poured into ice water (1.5 L), adjusted to pH 7, concentrated, and extracted with EtOAc (1.5 L). The combined organic layers were washed with brine, dried over Na2SO4, concentrated, and pur...

Claims

1. Compound of formula (I): The substituents have the following meanings: R 1 It is hydrogen; R 2 It is hydrogen; R 3 It is a halogen, cyano, or C1-C3 haloalkoxy group; R 4 It is hydrogen or halogen; R 5 It is hydrogen, halogen, or C1-C3 alkyl; R 6 It is hydrogen; R 7 and R 8 Together with the carbon atoms they are bonded to, they form saturated or partially unsaturated 3, 4, 5, or 6-membered monocyclic heterocycles W or 6, 7, or 8-membered bicyclic heterocycles W, which, in addition to the aforementioned carbon atoms, contain q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x atoms selected from NR. d and NC(O)OR d The unit, wherein the ring is bounded by n groups R g replace; R 9 It is hydrogen; X is the bond and Y is Z, where Z is a 4, 5, 6, 7, or 8-membered saturated or partially unsaturated monocyclic carbon ring, surrounded by the CO2R group. e And replaced by 0 or 1 fluorine atom; or Z is a 5, 6, 7, or 8-membered saturated or partially unsaturated bicyclic carbon ring, surrounded by the CO2R group. e And substituted with 0 or 1 C1-C4 alkyl group; or Z is a 5- or 6-membered saturated or partially unsaturated monocyclic heterocycle containing one oxygen atom or one sulfur atom as a ring member, wherein the heterocycle is bound by the CO2R group. e Replace; or Z is a 5-membered heteroaromatic ring containing 1, 2, 3, or 4 nitrogen atoms as ring members, wherein the heteroaromatic ring is substituted by 0 or 1 C1-C4 alkyl group; or X is a bond and Y is a C1-C6 alkyl group, with a CO2R group as the bond. e CONR b R h or CONR e1 SO2R a And it is substituted with 0 or 1 C1-C4 alkoxy group; or X is a bond and Y is a C2-C8 ynyl group; or X is X 6 Where R 10 -R 13 Independently hydrogen; and Y is a group with CO2R e Substituted C1-C4 alkyl groups; R a It is a C1-C6 alkyl group; R b It is hydrogen; R d Each is independently hydrogen or C1-C6 alkyl; R e1 It is hydrogen or C1-C4 alkyl; R e Each of the following is independently hydrogen, C1-C6 alkyl, which is unsubstituted or substituted with 1, 2 or 3 fluorine or chlorine atoms or with 1 group selected from C1-C2 alkoxy, C1-C3 alkylsulfonyl, C1-C3 alkylthio, phenylsulfonyl, phenylthio and furanyl; or is C2-C4 alkynyl or C3-C6 cycloalkyl-C1-C3 alkyl; R g It is a C1-C3 alkyl group; or two R atoms bonded to the same carbon atom. g Together they form a methylene group (=CH2); R h It is a C1-C6 alkyl group substituted with 0 or 1 cyano group; or a C2-C4 alkynyl group; n is 0, 1, or 2; q can be 1, 2, 3, 4, 5, or 6; u is 0, 1, or 2; v is 0 or 1; w is 0 or 1; x is 0 or 1; The condition is that the sum of u, v, w, and x is 1 or 2; This includes its agricultural salts, stereoisomers, and tautomers.

2. The compound claimed in claim 1, wherein R 5 It is hydrogen or halogen.

3. The compound claimed in claim 1, wherein... u is 1 or 2, v is 0, w is 0 and x is 0; or u is 0 or 1, v is 1, w is 0 and x is 0; or u is 0 or 1, v is 0, w is 1 and x is 0; or u is 0, v is 0, w is 0 and x is 1.

4. The compound claimed in claim 2, wherein... u is 1 or 2, v is 0, w is 0 and x is 0; or u is 0 or 1, v is 1, w is 0 and x is 0; or u is 0 or 1, v is 0, w is 1 and x is 0; or u is 0, v is 0, w is 0 and x is 1.

5. The compound claimed in any one of claims 1-4, wherein the substituents have the following meanings: R 7 and R 8 Together with the carbon atoms they are bonded to, they form a saturated or partially unsaturated 4-5 member monocyclic heterocycle W, which, in addition to the carbon atom, contains q carbon atoms and u oxygen atoms, and wherein the ring is bounded by n groups R. g Replace, where u is 1 or 2, and q is 1, 2, or 3.

6. The compound claimed in any one of claims 1-4, wherein the compound is selected as a product of R 7 and R 8 NR of the ring members of the formed ring d and NC(O)OR d R in the unit d Each is independently hydrogen or C1-C3 alkyl.

7. The compound claimed in claim 5, wherein the compound is selected as a product of R 7 and R 8 NR of the ring members of the formed ring d and NC(O)OR d R in the unit d Each is independently hydrogen or C1-C3 alkyl.

8. A composition comprising at least one compound claimed in any one of claims 1-7 and an adjuvant commonly used in formulating article protection mixtures.

9. The composition claimed in claim 8, wherein it comprises other herbicides.

10. Use of the compound claimed in any one of claims 1-7 or the composition claimed in claim 8 or 9 in the control of unwanted plants.

11. A method for controlling unwanted plants, comprising applying a herbicidal effective amount of at least one compound claimed in any one of claims 1-7 or a composition claimed in claim 8 or 9 to the plant, its seeds and / or its growing area.

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