Herbicidal combinations and compositions

Abstract

The present invention relates to novel herbicidally active compound combinations and / or compositions comprising a substituted isoxazoline-carboxamide or an agrochemically acceptable salt thereof and a substituted N-phenyluracil. They can be used for controlling weeds in crops of useful plants and have a particularly good effect.

Description

[0001] This invention relates to novel herbicidal active compound complexes and / or compositions comprising substituted isoxazoline-formamide or its agrochemically acceptable salt and substituted N-phenyluracil. They can be used to control weeds in a variety of beneficial plant crops and have particularly good effects.

[0002] Substituted N-phenyluracil is known as an effective herbicide, as can be seen from patent applications / patent publications such as WO2021 / 139482 A1, WO 2010 / 145992 A1, WO 2010 / 038953 A1, WO 2016 / 095768 A1, WO 2021 / 143677 A1, WO 2023 / 285222 A1, US 6403534 B1, WO 2023 / 228935 A1, US 6403534 B1, WO2023 / 228935 A1, EP 4353082 A1, and WO 2023 / 197899 A1. These compounds can be used non-selectively or selectively depending on the time and crop. However, their activity and compatibility with crop plants are not entirely satisfactory under all conditions.

[0003] Substituted isoxazoline-formamides are known as effective herbicides, as exemplified by WO 2018 / 228985 A1 and WO2019 / 145245 A1. These compounds can be used non-selectively or selectively depending on the time and crop. However, their activity and compatibility with crop plants are not entirely satisfactory under all conditions.

[0004] Surprisingly, certain substituted isoxazoline-formamides have been found to be particularly advantageous as broad-spectrum conjugate formulations when used in conjunction with substituted N-phenyluracil as described below for the control of weeds in useful plant crops such as cereals, corn, and soybeans, with significant synergistic effects.

[0005] This invention provides a weed control compound comprising (a) A substituted isoxazoline-formamide of formula (I) or an agrochemically acceptable salt thereof (I) in G stands for OR 4 or NR 7 R 8 ; R 1 and R 2 Each represents hydrogen; R 3Represents (C1-C5)-alkyl, (C3-C6)-cycloalkyl, (C2-C5)-alkenyl, (C2-C5)-alkynyl or (C1-C5)-alkoxy, each optionally substituted "m" times by a substituent selected from halogen, cyano, (C1-C5)-alkoxy and hydroxyl. R 4 Represents hydrogen, or Representative (C1-C) 12 (C3-C7)-alkyl, (C3-C7)-cycloalkyl-(C1-C8)-alkyl, (C2-C8)-alkenyl, (C5-C6)-cycloalkenyl, (C1-C4)-alkylphenyl or (C2-C8)-ynyl, each optionally selected from halogen, cyano, (C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl, hydroxyl, S(O) n R 5 The substituents are replaced "m" times; R 5 Represents (C1-C8)-alkyl, (C2-C8)-alkenyl, (C3-C6)-cycloalkyl, benzyl, CON((C1-C3)-alkyl)2 or (C1-C8)-alkyl-C(O)-(C1-C8)-alkyl, each optionally substituted m times by a substituent selected from halogens and cyano groups; R 6 Represents hydrogen, or Represents (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C3-C8)-alkenyl or (C3-C8)-alkynyl, each optionally substituted m times by a substituent selected from halogen, cyano and (C1-C2)-alkoxy. R 7 R 8 Each of these independently represents hydrogen, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl, N((C1-C3)-alkyl)2, and S(O). n R 5 ; or R 7 and R 8 Together with the nitrogen atoms they are attached to, they form saturated or partially or completely unsaturated five-, six-, or seven-membered rings. In addition to nitrogen atoms, these rings may contain "r" carbon atoms and "o" oxygen atoms, and are optionally selected from halogens, (C1-C6)-alkyl groups, halogen-(C1-C6)-alkyl groups, oxo groups, and CO2R groups. 6 The substituents are replaced "m" times; Z represents Z-1 to Z-8: The arrows represent bonds to the CO-G groups in formula (I); X 2 X 4 and X 6 Each can represent either hydrogen or fluorine independently; X 3 and X 5 Each can independently represent hydrogen, chlorine, cyanide, or fluorine; or Represents (C1-C3)-alkyl, (C1-C3)-alkoxy, each optionally substituted m times with a substituent selected from fluorine or chlorine; m represents 0, 1, 2, 3, 4 or 5; n represents 0, 1, or 2; o represents 0, 1, or 2; r represents 3, 4, 5, or 6; and (b) One or more of B1 to B35 specified in Table 1 below: Table 1 The chemical structural names of the above-mentioned herbicides are all accompanied by a CAS RN (Chemical Abstracts Service Registry Number, if applicable). CAS RN is a widely accepted and used reference number used to clearly specify stereoisomers, esters, and salts.

[0006] definition halogen The representative groups are fluorine, chlorine, bromine, and iodine. Fluorine and chlorine groups are preferred.

[0007] alkylThis refers to a saturated straight-chain or branched hydrocarbon group having the specified number of carbon atoms in each case, such as C1-C6-alkyl groups, including methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, etc. 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.

[0008] alkenylThis refers to an unsaturated straight-chain or branched hydrocarbon group that has a specified number of carbon atoms and a double bond in any position, such as C2-C6 alkenyl groups, including vinyl, 1-propenyl, 2-propenyl, 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, etc. -Butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2 -pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-1-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1-butenyl, 3,3-Dimethyl-2-butenyl, 1-Ethyl-1-butenyl, 1-Ethyl-2-butenyl, 1-Ethyl-3-butenyl, 2-Ethyl-1-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1,1,2-Trimethyl-2-propenyl, 1-Ethyl-1-methyl-2-propenyl, 1-Ethyl-2-methyl-1-propenyl and 1-Ethyl-2-methyl-2-propenyl.

[0009] acetylinRepresents a straight-chain or branched hydrocarbon group having 2 to 8, preferably 2 to 6, carbon atoms and a triple bond in any position. Non-limiting examples include ethynyl, prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, 1-methylprop-2-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, 1-methylbut-2-ynyl, 1-methylbut-3-ynyl, 2-methylbut-3-ynyl, 3-methylbut-1-ynyl, 1,1-dimethylprop-2-ynyl, 1-ethylprop-2-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 1-methylpent-2-ynyl, 1-methyl The following are listed: 3-methylpentan-yne, 1-methylpentan-4-yne, 2-methylpentan-3-yne, 2-methylpentan-4-yne, 3-methylpentan-1-yne, 3-methylpentan-4-yne, 4-methylpentan-1-yne, 4-methylpentan-2-yne, 1,1-dimethylbutan-2-yne, 1,1-dimethylbutan-3-yne, 1,2-dimethylbutan-3-yne, 2,2-dimethylbutan-3-yne, 3,3-dimethylbutan-1-yne, 1-ethylbutan-2-yne, 1-ethylbutan-3-yne, 2-ethylbutan-3-yne, and 1-ethyl-1-methylpropan-2-yne.

[0010] Clarification: Alkynyl and Alkinyl are equivalent.

[0011] cycloalkyl This refers to a carbocyclic saturated ring system, preferably having 3-8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. In the case of optionally substituted cycloalkyl groups, this includes cyclic systems with substituents, as well as substituents having double bonds on the cycloalkyl group, such as alkylene groups like methylene.

[0012] AlkoxyThis refers to a saturated straight-chain or branched alkoxy group having the specified number of carbon atoms in each case, such as C1-C6-alkoxy groups, including methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, and 1,2-dimethylpropoxy. 1-Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1,1-Dimethylbutoxy, 1,2-Dimethylbutoxy, 1,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1,1,2-Trimethylpropoxy, 1,2,2-Trimethylpropoxy, 1-Ethyl-1-Methylpropoxy, and 1-Ethyl-2-Methylpropoxy. Halogen-substituted alkoxy groups refer to straight-chain or branched alkoxy groups having the number of carbon atoms specified in each case, wherein some or all of the hydrogen atoms in these groups may be replaced by the halogen atoms specified above, such as C1-C2-haloalkoxy groups, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-1,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, and 1,1,1-trifluoroprop-2-oxy.

[0013] The present invention also relates to all stereoisomers covered but not explicitly defined by formula (I) and mixtures thereof. However, for simplicity, compounds of formula (I) will always be referred to below, but this should be understood to mean not only pure compounds, but also (if appropriate) mixtures of isomers in different proportions.

[0014] Based on the properties of the substituents defined above, compounds of formula (I) possess acidic properties and can form salts, and, if suitable, can form internal salts or adducts with inorganic or organic bases or with metal ions. If compounds of formula (I) contain a hydroxyl group, carboxyl group, or other group that imparts acidic properties, these compounds can react with a base to form a salt. Suitable bases are, for example, hydroxides, carbonates, and bicarbonates of alkali metals and alkaline earth metals, especially hydroxides, carbonates, and bicarbonates of sodium, potassium, magnesium, and calcium, as well as ammonia, primary, secondary, and tertiary amines having (C1-C4)-alkyl groups, mono-, di-, and trialkylolamines of (C1-C4)-alkanols, choline and chlorocholine, and organic amines such as trialkylamines, morpholine, piperidine, or pyridine. These salts are compounds in which acidic hydrogen is replaced by agriculturally suitable cations, such as metal salts, especially alkali metal or alkaline earth metal salts, particularly sodium and potassium salts, or ammonium salts, salts with organic amines, or quaternary ammonium salts, for example having the formula [NRR´R´´R´´´]. + The cation, wherein R to R''' are each independently an organic group, especially alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkyl sulfonium salts and alkyl sulfoxide salts, such as (C1-C4)-trialkyl sulfonium salts and (C1-C4)-trialkyl sulfoxide salts.

[0015] Some compounds of formula (I) can form salts by adding suitable inorganic or organic acids to a basic group such as amino, alkylamino, dialkylamino, piperidinyl, morpholinyl, or pyridinyl. These salts can be mineral acids such as HCl, HBr, H₂SO₄, H₃PO₄, or HNO₃, or organic acids such as carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or sulfonic acids (e.g., p-toluenesulfonic acid). In such cases, these salts contain the conjugate base of the acid as an anion.

[0016] Suitable substituents, such as sulfonic acids or carboxylic acids, existing in a deprotonated form, can form internal salts with partially protonable groups, such as amino groups.

[0017] Methods for preparing the compounds in the herbicidal compound are known. Compound (a) was prepared according to the method disclosed in WO 2018 / 228985 A1. Compound (b) was prepared according to the methods disclosed in WO 2021 / 139482 A1, WO 2010 / 145992 A1, WO 2010 / 038953 A1, WO 2016 / 095768 A1, WO 2021 / 143677 A1, WO 2023 / 285222 A1, US 6403534B1, WO 2023 / 228935 A1, US 6403534 B1, WO 2023 / 228935 A1, EP 4353082 A1 and WO 2023 / 197899 A1.

[0018] The general definition of the compounds of this invention is shown in formula (I). The preferred substituents of the groups given in the above formula are illustrated below: Preferred Herbicidal compounds are compounds of formula (I) that are one of the compounds of formula (Ia) or their agrochemically acceptable salts. (Ia) in X 3 X 5 R 3 And G as described above; Z represents Z-1a, Z-1b,, Z-2a, Z-3a, Z-4a,, Z-5a, Z-6a, Z-7a,, Z-8a, Where Z-4a represents a mixture of structures Z-4b and Z-4c; Furthermore, Z-8a represents a mixture of structures Z-8b and Z-8c. Furthermore, the arrows indicate the bonding with the CO-G group in formula (Ia).

[0019] Especially preferred Herbicidal compounds are compounds of formula (Ia) that are one of the compounds in Table 2 or their agrochemically acceptable salts. (Ia) The definitions of Z-1a, Z-1b, Z-2a, Z-3a, Z-4a, Z-4c, Z-4b, Z-5a, Z-6a, Z-7a, and Z-8a are as described above.

[0020] Table 2: Examples of compounds of formula (Ia) Preferred It is a combination of formula (Ia) No. 1.68 and B1.

[0021] PreferredIt is a combination of formula (Ia) No. 1.68 and B2.

[0022] Preferred It is a combination of formula (Ia) No. 1.68 and B3.

[0023] Preferred It is a combination of formula (Ia) No. 1.68 and B4.

[0024] Preferred It is a combination of formula (Ia) No. 1.68 and B5.

[0025] Preferred It is a combination of formula (Ia) No. 1.68 and B6.

[0026] Preferred It is a combination of formula (Ia) No. 1.68 and B7.

[0027] Preferred It is a combination of formula (Ia) No. 1.68 and B8.

[0028] Preferred It is a combination of formula (Ia) No. 1.68 and B9.

[0029] Preferred It is a combination of formula (Ia) No. 1.68 and B10.

[0030] Preferred It is a combination of formula (Ia) No. 1.68 and B11.

[0031] Preferred It is a combination of formula (Ia) No. 1.68 and B12.

[0032] Preferred It is a combination of formula (Ia) No. 1.68 and B13.

[0033] Preferred It is a combination of formula (Ia) No. 1.68 and B14.

[0034] Preferred It is a combination of formula (Ia) No. 1.68 and B15.

[0035] Preferred It is a combination of formula (Ia) No. 1.68 and B16.

[0036] Preferred It is a combination of formula (Ia) No. 1.68 and B17.

[0037] PreferredIt is a combination of formula (Ia) No. 1.68 and B18.

[0038] Preferred It is a combination of formula (Ia) No. 1.68 and B19.

[0039] Preferred It is a combination of formula (Ia) No. 1.68 and B20.

[0040] Preferred It is a combination of formula (Ia) No. 1.68 and B21.

[0041] Preferred It is a combination of formula (Ia) No. 1.68 and B22.

[0042] Preferred It is a combination of formula (Ia) No. 1.68 and B23.

[0043] Preferred It is a combination of formula (Ia) No. 1.68 and B24.

[0044] Preferred It is a combination of formula (Ia) No. 1.68 and B25.

[0045] Preferred It is a combination of formula (Ia) No. 1.68 and B26.

[0046] Preferred It is a combination of formula (Ia) No. 1.68 and B27.

[0047] Preferred It is a combination of formula (Ia) No. 1.68 and B28.

[0048] Preferred It is a combination of formula (Ia) No. 1.68 and B29.

[0049] Preferred It is a combination of formula (Ia) No. 1.68 and B30.

[0050] Preferred It is a combination of formula (Ia) No. 1.68 and B31.

[0051] Preferred It is a combination of formula (Ia) No. 1.68 and B32.

[0052] Preferred It is a combination of formula (Ia) No. 1.68 and B33.

[0053] Preferred It is a combination of formula (Ia) No. 1.68 and B34.

[0054] Preferred It is a combination of formula (Ia) No. 1.68 and B35.

[0055] return Preferred It is a combination of (Ia) No. 1.100 and B1.

[0056] return Preferred It is a combination of (Ia) No. 1.100 and B2.

[0057] return Preferred It is a combination of (Ia) No. 1.100 and B3.

[0058] return Preferred It is a combination of (Ia) No. 1.100 and B4.

[0059] return Preferred It is a combination of (Ia) No. 1.100 and B5.

[0060] return Preferred It is a combination of (Ia) No. 1.100 and B6.

[0061] return Preferred It is a combination of (Ia) No. 1.100 and B7.

[0062] return Preferred It is a combination of (Ia) No. 1.100 and B8.

[0063] return Preferred It is a combination of (Ia) No. 1.100 and B9.

[0064] return Preferred It is a combination of (Ia) No. 1.100 and B10.

[0065] return Preferred It is a combination of (Ia) No. 1.100 and B11.

[0066] return Preferred It is a combination of (Ia) No. 1.100 and B12.

[0067] return Preferred It is a combination of (Ia) No. 1.100 and B13.

[0068] return Preferred It is a combination of (Ia) No. 1.100 and B14.

[0069] return Preferred It is a combination of (Ia) No. 1.100 and B15.

[0070] return Preferred It is a combination of (Ia) No. 1.100 and B16.

[0071] return Preferred It is a combination of (Ia) No. 1.100 and B17.

[0072] return Preferred It is a combination of (Ia) No. 1.100 and B18.

[0073] return Preferred It is a combination of (Ia) No. 1.100 and B19.

[0074] return Preferred It is a combination of (Ia) No. 1.100 and B20.

[0075] return Preferred It is a combination of (Ia) No. 1.100 and B21.

[0076] return Preferred It is a combination of (Ia) No. 1.100 and B22.

[0077] return Preferred It is a combination of (Ia) No. 1.100 and B23.

[0078] return Preferred It is a combination of (Ia) No. 1.100 and B24.

[0079] return Preferred It is a combination of (Ia) No. 1.100 and B25.

[0080] return Preferred It is a combination of (Ia) No. 1.100 and B26.

[0081] return Preferred It is a combination of (Ia) No. 1.100 and B27.

[0082] return Preferred It is a combination of (Ia) No. 1.100 and B28.

[0083] return Preferred It is a combination of (Ia) No. 1.100 and B29.

[0084] return PreferredIt is a combination of (Ia) No. 1.100 and B30.

[0085] return Preferred It is a combination of (Ia) No. 1.100 and B31.

[0086] return Preferred It is a combination of (Ia) No. 1.100 and B32.

[0087] return Preferred It is a combination of (Ia) No. 1.100 and B33.

[0088] return Preferred It is a combination of (Ia) No. 1.100 and B34.

[0089] return Preferred It is a combination of (Ia) No. 1.100 and B35.

[0090] The aforementioned herbicidal compound can be used in combination with a safener, such as isoxadifen-ethyl, cyprosulfamide, mefenpyr-diethyl, cloquintocet-mexyl, and methyl-{[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate, including its hydrates and salts, such as its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium, or phosphonium salts.

[0091] Surprisingly, the aforementioned active compound conjugates, namely (a) substituted isoxazoline-formamides of general formula (I) and / or their salts, and (b) one or more of B1 to B35, have been found to have exceptionally high herbicidal activity—higher than the simple superposition (synergistic effect) of the activity of herbicides applied alone—and can be used in a wide range of crops, particularly cereals (especially wheat and barley), soybeans, corn, rapeseed / canola, sugarcane, cotton, and tree fruits, nuts, and vines such as custard apples, citrus, nuts, pome fruits, small fruits and stone fruits (including vines), bananas, olives, and palm crops, for weed control.

[0092] The active compound conjugate according to the present invention can be applied before and after plant emergence, i.e., by pre-emergence and post-emergence methods.

[0093] Synergistic effects have been observed when active ingredients (a) and (b) are applied in combination, but they also frequently occur when applied separately. Herbicides (a) or (b) or herbicide-combination (a) and (b) can also be applied in multiple portions (sequentially). For example, post-emergence application can be performed after one or more pre-emergence applications, or after an early post-emergence application followed by a mid-to-late or late-term post-emergence application. Simultaneous or immediate continuous application of the active ingredients of the corresponding combination is preferred, if it is appropriate to apply in multiple portions. However, it is also possible to apply the individual active ingredients of the combination at different times, and this may be advantageous in certain cases. Other crop protection products can also be integrated into the application system, such as the other active ingredients mentioned (other herbicides, fungicides, insecticides, acaricides, etc.) and / or the application of various adjuvants, adjuvants, and / or fertilizers.

[0094] The active compound conjugates according to the invention can be used in, for example, the following plants: Dicotyledonous weeds Genus: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia Thistle (Cirsium), Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.

[0095] Dicotyledonous crops: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita, Helianthus.

[0096] Monocotyledonous weeds Genera of grasses: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Bermuda grass The genera include Cynodon, Monochooria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, and Apera.

[0097] Monocotyledonous crops : Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

[0098] However, the use of the active compound conjugates according to the invention is by no means limited to these genera, but is equally applicable to other plants. According to the invention, crop plants include all plants and plant varieties, including transgenic plants and plant varieties, where synergistic effects may also occur in transgenic plants and plant varieties.

[0099] The present invention also relates to a method for reducing crop damage by treating crop seeds with a safener before sowing. In addition to using herbicide / safener combinations and compositions comprising them, this method is also highly applicable for protecting crops from herbicide damage in pre- and post-emergence treatments.

[0100] Composition In addition to the combinations according to the present invention, the compositions within the scope of this invention also contain one or more other components selected from formulation adjuvants, additives commonly used in crop protection, and other agrochemically active compounds (e.g., fungicides, insecticides, acaricides, etc.).

[0101] additive Additives include, for example, fertilizers and colorants.

[0102] Active compounds or active compound conjugates can be converted into conventional formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting powders, pastes, soluble powders, granules, suspension emulsion concentrates, natural and synthetic materials impregnated with active compounds, and ultrafine capsules in polymers.

[0103] These formulations are produced in a known manner, for example by mixing the active compound with a filler (i.e., a liquid solvent and / or a solid carrier), and optionally by using a surfactant (i.e., an emulsifier and / or a dispersant and / or a foaming agent).

[0104] If the filler used is water, organic solvents, for example, can be used as auxiliary solvents. Suitable liquid solvents are mainly: aromatic hydrocarbons, such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzene, vinyl chloride, or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins (e.g., petroleum fractions, mineral oils, and vegetable oils); alcohols, such as butanol or ethylene glycol, and their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; highly polar solvents, such as dimethylformamide and dimethyl sulfoxide; and water.

[0105] Suitable solid carriers include, for example, ammonium salts and ground natural minerals (e.g., kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth), and ground synthetic minerals (e.g., finely powdered silica, alumina, and silicates); suitable solid carriers for particles include, for example, crushed and graded natural rocks (e.g., calcite, marble, pumice, sepiolite, and dolomite), and synthetic particles of inorganic and organic powders, as well as organic material particles such as sawdust, coconut shells, corn cobs, and tobacco stems; suitable emulsifiers and / or foaming agents include, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers (e.g., alkyl aryl polyethylene glycol ethers), alkyl sulfonates, alkyl sulfates, aryl sulfonates, and protein hydrolysates; suitable dispersants include, for example, lignin sulfite waste and methylcellulose.

[0106] Thickeners may be used in the formulation, such as carboxymethyl cellulose and natural and synthetic polymers (in the form of powder, granules or latex), such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids (such as cephalin and lecithin) and synthetic phospholipids. Other possible additives are mineral oils and vegetable oils.

[0107] Colorants such as inorganic pigments (e.g., iron oxide, titanium dioxide, and Prussian blue) and organic dyes (e.g., alizarin dyes, azo dyes, and metal phthalocyanine dyes) as well as micronutrients (e.g., salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc) can be used.

[0108] The formulation typically contains 0.1 to 95% by weight of the active compound (including a safener), preferably 0.5 to 90% by weight.

[0109] The active compound conjugates / compositions according to the present invention are generally used in the form of finished formulations. However, the active compounds contained in the active compound conjugates / compositions may also be used as individual formulations, i.e., as tank mixes.

[0110] These novel active compound conjugates, whether used directly or in formulation form, can be mixed with other known herbicides, or used in finished formulations or tank mixes. They can also be used in mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, growth factors, phytonutrients, and soil conditioners. For certain specific applications, particularly in post-emergence applications, it may be advantageous to add plant-tolerant mineral or vegetable oils (e.g., the commercially available formulation "Rako Binol") or ammonium salts (e.g., ammonium sulfate or ammonium thiocyanate) as additives to the formulation.

[0111] These novel active compound conjugates can be used directly, either in their formulation form or by further dilution into various forms of application, such as ready-to-use solutions, suspensions, emulsions, powders, pastes, and granules. They are used in conventional ways, such as by washing, spraying, atomizing, dusting, or dispersing.

[0112] The beneficial effects of the active compound conjugates according to the invention on crop compatibility are particularly pronounced at certain amounts of herbicides and safeners.

[0113] The application amount of the active compound complex according to the invention can vary within a certain range; they are particularly dependent on weather and soil factors.

[0114] Generally, the application rate of herbicides is 0.1 to 500 g ai / ha. Preferred The concentration ranges from 1.0 to 250 g ai / ha.

[0115] Depending on the effective application rate, the weight ratio of (a) to (b) is typically 1:10000 to 5000:1. Preferred The ratio ranges from 1:1000 to 500:1. More The ratio is between 1:100 and 50:1, and Optimal Selection The ratio is 1:10 to 5:1.

[0116] The herbicidal conjugates of the present invention can also be combined with other herbicides and plant growth regulators, for example, to complement the activity spectrum or to exert additional synergistic effects. Conjugates that can be used in mixtures or tank mixes with compounds according to the invention are, for example, based on known active ingredients that inhibit, for example, acetyllactone synthase, acetyl-CoA carboxylase, cellulase, enolpyruvate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytopene desaturase, photosystem I, photosystem II, and protoporphyrinogen oxidase, as can be seen, for example, from Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006, the corresponding “e-Pesticide Manual Version 4 (2006)”, and the references cited therein. More product names and "generic names" are listed in the "Compendium of Pesticide Common Names" (available online at http: / / www.alanwood.net / pesticides).

[0117] Examples of known herbicides that can be combined with the compounds of this invention include the following active ingredients (note: these compounds are named either by their common names as prescribed by the International Organization for Standardization (ISO) or by their chemical names, in some cases together with their standard code numbers) and always cover all forms of use, such as acids, salts, esters, and isomers (e.g., stereoisomers and optical isomers). This list contains one, and in some cases more than one, application form: Acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicabazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, cyclopropionic acid (am Inocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-dimethylammonium, aminopyralid-tripromine, amitrole, ammonium sulfamate, anilofos, asulam, asulam-potassium, asulam sodium. Sodium, atrazine, azafenidin, azimsulfuron, beflubutamid, (S)-(-)-beflubutamid, beflubutamid-M, benzolin, benzolin-ethyl, benzolin-dimethylammonium, benzolin-potassium, benzfluralin, benzuresate, benzsulfuron, benzsulfuron-methyl, benzulide, benzazone, benzazone-sodium, benzobicyclon, benzofenap.Bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bipyrazone, bispyribac, bispyribac-sodium, bixlozone, bromacil, bromacil-lithium, bromacil-sodium, bromobutide, bromofenoxim oxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassium, bromoxynil-heptanoate, bromoxynil-octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxyd IM, Butylate, Cafenstrole, Cambendichlor, Carbetamide, Carfentrazone, Carfentrazone-ethyl, Chloramben, Chloramben-ammonium, Chloramben-diolamine, Chloramben-methyl, Chloramben-methylammonium, Chloramben-sodium, Chlorbromuron, Chlorfenac, Chlorfenac-ammonium, Chlorfenac-sodium, Chlorfenprop, Chlorfenprop-methyl, Chlorflurenol, Chlorflurenol-methyl, Chloridazon, Chlorimuron.Chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorsulfuron, chlorthal, dimethyl chlorthalate, monomethyl chlorthalate, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cinmethylin, i.e. (1R, (2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane), exo-(-)-cycloheptanyl ether (exo-(-)-cinmethylin), i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane), cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl Isoxaben (clomazone), clomeprop, clopyralid, clopyralid-methyl, clopyralid-olamine, clopyralid-potassium, clopyralid-tripomine, cloransulam, cloransulam-methyl, cumyluron, cyanamide Cyazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D (including its ammonium salt, butoxyethyl ester, butyl ester, choline, diethylammonium salt, dimethylammonium salt, diethanolamine salt, propylene glycol butyl ether ester, dodecyl ammonium salt, ethylhexyl ester, ethyl ester, 2-ethylhexyl ester, heptyl ammonium salt, isobutyl ester, isooctyl ester, isopropyl ester,Isopropylammonium salts, lithium salts, methyl heptyl ester, methyl ester, potassium salts, tetradecylammonium salts, triethylammonium salts, triisopropanolammonium salts, tripromine and triethanolamine salts), 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium salt, 2,4-DB-isooctyl ester, 2,4-DB-potassium salt and 2,4-DB-sodium salt, daimuron (dymron), dalapon, dalapon-calcium, dalapon-magnesium, dalapon-sodium, dazomet, n-decanol, 7-deoxy-D-sedoheptulose, betaine (d... esmedipham), destosyl-pyrazolate (DTP), dicamba and its salts (e.g., dicamba-biproamine, dicamba-N,N-bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolamine). dicamba, diethylammonium, isopropylammonium, methyl dicamba, monoethanolamine, potassium dicamba, sodium dicamba, triethanolamine dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, butoxyethyl dichlorprop, dichlorprop, dimethylammonium dichlorprop.2,4-D ethylhexyl propionate (dichlorprop-etexyl), 2,4-ethylammonium propionate (dichlorprop-ethylammonium), 2,4-isoctyl propionate (dichlorprop-isoctyl), 2,4-methyl propionate (dichlorprop-methyl), 2,4-potassium propionate (dichlorprop-potassium), 2,4-sodium propionate (dichlorprop-sodium), purified 2,4-propionic acid (dichlorprop-P), purified 2,4-dimethylammonium propionate (dichlorprop- P-dimethylammonium, dichlorprop-P-etexyl, dichlorprop-P-potassium, dichlorprop-sodium, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, difenzoquat methanesulfonic acid Difenzoquat-metilsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, diflubenzuron Nitroamine, dinoterb, dinoterb-acetate, diphenamid, diquat, diquat-dibromid, diquat-dichloride, dithiopyr, diuron, DNOC, DNOC ammonium, DNOC potassium, DNOC sodium, endothalEndothal-diammonium, endothal-dipotassium, endothal-disodium, Epyrifenacil (S-3100), EPTC, esprocarb, etalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethyozin, ethofumesate, ethoxy fen), ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5231 (N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazole-1-yl]phenyl]ethanesulfonamide), F-7967 (3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidin-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop ethyl ester ( fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flamprop, flamprop-isoproyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, pyrimisulfuron ( The following herbicides are listed: flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P, fluazifop-P-butyl, flucarbazone, and flucarbazone-sodium.Flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, fluorenol-butyl, fluorenol-dimethylammonium salt and fluorenol-methyl ester -methyl), fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupropanate-sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridone, flurochlor idone), fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, foramsulfuron-sodium Sodium salt, fosamine, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate.Glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium, and glyphosate-trimethylsulfonate ium), H-9201, namely O-(2,4-dimethyl-6-nitrophenyl)-O-ethylisopropylthiophosphoramide ester, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-e thoxyethyl), haloxyfop-methyl, haloxyfop-P-methyl, haloxifop-sodium, hexazinone, HNPC-A8169 (prop-2-yn-1-yl(2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propionate), HW-02 (2,4-dichlorophenoxy)acetic acid 1-(dimethoxyphosphoryl)ethyl ester), hydantocidin, imidazolic acid (imazamethabenz), methyl imidazolate (imaza... Methabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, isopropylammonium, imazaquin, imazaquin-ammonium, imazaquin-methyl, and imazethapyr.Imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium, ioxynil, lithium ioxynil, octanoate, potassium ioxynil, and sodium ioxynil (-lithium, -octanoate, -potassium and...) -sodium), triazolecarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, namely 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-di Hydrogen-1,2-oxazole, ketospiradox, ketospiradox-potassium, lactoferrin, lenacil, linuron, MCPA, MCPA-butoxyethyl ester, MCPA-butyl ester, MCPA-dimethylammonium salt, MCPA-diethanolamine salt, MCPA-2-ethylhexyl ester, MCPA-ethyl ester, MCPA-isobutyl ester, MCPA-isooctyl ester MCPA-isopropyl ester, MCPA-isopropylammonium salt, MCPA-methyl ester, MCPA-ethanolamine salt, MCPA-potassium salt, MCPA-sodium salt and MCPA-triethanolamine salt, MCPB, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium salt, 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-butotyl), 2-methyl-4-chloropropionic acid dimethylammonium salt (mecoprop-demethylammonium), 2-methyl-4-chloropropionic acid diethanolamine salt (mecoprop-diolamine), 2-methyl-4-chloropropionic acid ethylhexyl ester (mecoprop-etexyl), mecoprop-ethadyl, 2-methyl-4-chloropropionic acid isooctyl ester (mecoprop-isoctyl), 2-methyl-4-chloropropionic acid methyl ester (mecoprop-methyl), 2-methyl-4-chloropropionic acid potassium salt (mecoprop-potassium)Sodium 2-methyl-4-chloropropionate (mecoprop-sodium), triethanolamine 2-methyl-4-chloropropionate (mecoprop-trolamine), purified 2-methyl-4-chloropropionate (mecoprop-P), butoxyethyl 2-methyl-4-chloropropionate (butoxyethyl 2-methyl-4-chloropropionate), dimethyl ammonium 2-methyl-4-chloropropionate (mecoprop-diolamine), 2-ethylhexyl 2-methyl-4-chloropropionate (mecoprop-potassium), mefenacet, mefluidide, mefluidide diethanolamine, mefluidide potassium, mesosulfuron, mesosulfuron methyl, and mesosulfuron sodium. Salt, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, metiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuryl furon-methyl), MT-5950, i.e., N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, NC-656, i.e., 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, neburon, nicosulfuron.Nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat-dichloride, paraquat-dimethylsulfate, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, petroleum oils), phenmedipham, phenmedipham-ethyl, phenmedipham, picloram, picloram-dimethylammonium, picloram-etexyl, picloram-isoctyl, picloram-methyl, picloram-olamine, picloram-potassium, picloram-t Riethylammonium, picloram-tripromine, picloram-trolamine, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlorPropanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufenic acid, pyraflufenic acid Pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyrazosulfuron-methyl ridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinclorac-dimethylammonium, quinclorac-methylammonium clorac-methyl), quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201, namely 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, rimsulfuron.Saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzyl) Ester, SYP-300, namely 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts (e.g., TCA-ammonium salt, TCA-calcium salt, TCA-ethyl ester, TCA-magnesium salt, TCA-sodium salt), tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, etc. Terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thaxtomin, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil Tolpyralate, toramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron-methyl, tribenuron-butotyl, and tribenuron-choline.Trilopyr-ethyl, trilopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron-methyl, triflusulfuron, urea sulfate sulfate), Vernolate, XDE-848, ZJ-0862, namely 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5-carboxylic acid ethyl ester, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5- 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohexyl-1-en-1-yl)carbonyl]-6-methylpyridazine-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-5-yl) methyl ketone 1-Methyl-4-[(3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophene-5-yl)carbonyl]-1H-pyrazol-5-ylpropane-1-sulfonate; 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazol-4-carboxylic acid ester; cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole- 6-yl)pyridine-2-carboxylic acid ester, prop-2-yn-1-yl4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid ester, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid,Ethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indol-6-yl)pyridine-2-carboxylate, methyl 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[1-(2,2-dimethylpropionyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)] Methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, imidazolidinyl-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidinyl-2-one Abscisic acid, acibenzolar, acibenzo-S-methyl, 1-aminocyclopropyl-1-ylcarboxylic acid and its derivatives, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, brassinolide ethyl, catechin, chitosan oligosaccharide (CO; the difference between CO and LCO is that CO lacks the side-chain fatty acids characteristic of LCO. CO is sometimes called N-acetylchitosan oligosaccharide, and it is also composed of GlcNAc residues, but its side-chain modification makes it different from chitin molecules [(C8H 13 NO5) n [CAS number 1398614] and chitosan molecules [(C5H 11 NO4) n [CAS No. 9012764]), chitin compounds, chlormequat chloride, cytosolic acid, cyclopropionic acid amide, 3-(cycloprop-1-enyl)propionic acid, butyrylhydrazine, dazomet, sodium dazomet, n-decanol, cytosolic acid, sodium cytosolic acid, cytosolic acid dipotassium, cytosolic acid disodium and mono(N,N-dimethylalkylammonium), ethephon, flubendiamide, fluorene butyl ester, fluorene butyl ester, fluorene butyl ester methyl ester, furazolidone, chlorpyrifos, gibberellin, antidote, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, thiabendazole, jasmonic acid, jasmonic acid or its derivatives (e.g., methyl jasmonic acid), lipoch-oligosaccharides (LCO, sometimes referred to as symbiotic nodule (Nod) signal (or Nod factor) or Myc factor, by β-1,4-linked NThe oligosaccharide backbone is composed of α-acetyl-D-glucosamine ("GlcNAc") residues, with N-linked fatty acyl chains condensed at its non-reducing ends. According to existing technology, the differences of LCO lie in the number of GlcNAc residues in the backbone, the length and saturation of the fatty acyl chain, and the substitution of reducing sugar and non-reducing sugar residues), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazine, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3'-methylabscisic acid, 2-(1-naphthyl)acetamide, 1-naphthacetic acid, 2-naphthoxyacetic acid, nitrophenol salt mixtures, 4-oxo-4-[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid, N-phenyl-o-carbamoylbenzoic acid, cyclohexanoic acid, calcium cyclohexanoate, propyl dihydrojasmonate, salicylic acid, methyl salicylate, strigolactone, tetrachloronitrobenzene, thidiazuron, triacontanol, anti-retromethorphan, anti-retromethorphan ethyl ester, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9 H -Purine-6-amine.

[0118] If the corresponding generic name contains multiple forms of active ingredient, the name is preferably defined in the commercially available form.

[0119] Each of the other active ingredients mentioned (= Active ingredient (C) (C1) (C2) (e.g.) can preferably be combined with the binary compound of the present invention according to scheme (a)+(b)+(C) ) or according to scheme (a)+(b)+(C1) )+(C2 Combined with, etc.

[0120] The amount mentioned is the application rate (ga.i. / ha = grams of active substance per hectare) and thus also defines the proportion of co-formulated, premixed, tank-mixed or sequentially applied active ingredients.

[0121] These compounds / combinations can be applied both pre-emergence and post-emergence. This is applicable both before and after the emergence of harmful plants, as well as for selective control of harmful plants before and after the emergence of crop plants. Mixed forms are also possible, for example, for controlling harmful plants before or after the emergence of crop plants.

[0122] The active ingredient complexes / compositions of the present invention are suitable for controlling broad-spectrum weeds on non-crop lands, roads, railway facilities, industrial areas (“industrial weed control”), or in plantation crops (e.g., in temperate, subtropical, and tropical climates or regions). Examples of plantation crops include oil palm, nuts (e.g., almonds, hazelnuts, walnuts, macadamia nuts), coconuts, berries, rubber trees, citrus fruits (e.g., oranges, lemons, tangerines), bananas, pineapples, cotton, sugarcane, tea, coffee, cocoa, etc. They are also suitable for cultivation of fruit trees (e.g., pome fruits such as apples, pears, cherries, mangoes, kiwifruit, etc.) and grape cultivation. The complexes / compositions can also be used for seed preparation (“non-selective,” “no-till,” or “zero-till” methods) or for post-harvest treatment (“chemical fallow”). Possible applications of the active ingredient complexes also extend to weed control in tree crops, such as Christmas tree seedlings or eucalyptus crops, in each case applied before or after planting (including top-top treatment).

[0123] The aforementioned compounds / compositions can also be used to control unwanted plant growth in economically important crops (“useful plants”), pastures and grasslands / lawns, and plantation crops, such as wheat (durum and soft wheat), corn, soybeans, sugar beets, sugarcane, cotton, rice, legumes (e.g., dwarf beans and broad beans), flax, barley, oats, rye, triticale, potatoes, and millet / sorghum. Plantation crops, especially pome fruits (apples, pears, papayas), currant species (blackberries, raspberries), citrus fruits, plum species (cherries, nectarines, apricots), nuts (walnuts, pecans, hazelnuts, cashews, macadamia nuts), mangoes, cocoa, coffee, grapes (for food or wine), palm trees (e.g., oil palms, date palms, coconut palms), eucalyptus, persimmons, persimmons, rubber, pineapples, bananas, avocados, lychees, and forest plants (Eucalyptus, Pinaceae, Spruceaceae, Meliaceae, etc.).

[0124] The herbicidal active ingredient complexes of the present invention exhibit synergistic effects in terms of herbicidal action and selectivity in their respective forms of application (i.e., herbicidal products), and also have a favorable effect on the weed spectrum. They possess excellent herbicidal efficacy against a broad spectrum of economically important monocot and dicot annual pests. The active ingredients also provide good control against perennial pests that are difficult to control and can produce seedlings from rhizomes, rootstocks, or other perennial reproductive organs.

[0125] For application, the active ingredient combination can be applied to plants (e.g., harmful plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), seeds (e.g., grains, seeds or vegetative reproductive organs such as tubers or part of a seedling with buds) or areas of plant growth (e.g., growing areas).

[0126] The substance can be applied before sowing (or, if appropriate, by incorporation into the soil), before emergence, or after emergence. In plantation crops, it is preferred to apply it pre-emergence after early sowing or post-emergence to control harmful plants that have not yet emerged or have already emerged. Application can also be integrated into a weed management system and applied repeatedly in stages (sequential application).

[0127] Specific examples of some representative monocotyledonous and dicotyledonous weeds that can be controlled by the combination / composition according to the invention are as follows, but this enumeration is not intended to impose limitations on any particular species.

[0128] Among monocotyledonous weed species, annuals include those from genera such as Aegilops, Agrostis, Creeping japonica, Amaranthus, Ficus, Oat, Brassica, Bromus, Bermudagrass, Crataegus pinnatifida, Crataegus pinnatifida, Barnyardgrass, Water chestnut, Goosegrass, Eriobotrya, Wild millet, Festuca, Eriobotrya, Imperata, Common grass, Heteropogon, Imperata, Lepidium, Ryegrass, Raindrop, Millet, Paspalum, Rhus, Poa, Coot, Arrowhead, Curcuma, Foxtail, Sorghum, Sedge, and Cyperus.

[0129] In the case of dicotyledonous weed species, the spectrum of action extends to species such as *Abutilon*, *Amaranthus*, *Raphanus*, *Abutilon*, *Chrysanthemum*, *Rosa minima*, *Artemisia*, *Acer palmatum*, *Daisy*, *Bidens pilosa*, *Capsella*, *Ligustrum*, *Cassia*, *Centipeda*, *Pteris*, *Convolvulus*, *Datura*, *Heliotropium*, *Rumex acetosa*, *Gerberis*, *Salix matsudana*, *Euphorbia*, *Euphorbia milii*, *Achyranthes*, *Gynostemma*, *Geranium*, *Hibiscus*, *Ipomoea*, and others. Genus: *Skin*, *Sesamum*, *Hedyotis*, *Heliotropium*, *Chrysanthemum*, *Mentha*, *Indigofera*, *Salvia*, *Forget-me-not*, *Papaver*, *Ipomoea*, *Plantago*, *Polygonum*, *Portulaca*, *Ranunculus*, *Radix*, *Radix*, *Gnaphalium*, *Erigeron*, *Salvia*, *Senecio*, *Senecio*, *Rosa multiflora*, *Mustard*, *Solanum*, *Solanum*, *Sonchus*, *Platycodon*, *Stellaria*, *Taraxacum*, *Iris*, *Trifolium*, *Urtica*, *Veronica*, *Viola*, *Xanthium*.

[0130] If the active ingredient complex of the present invention is applied to the soil surface before germination, it either completely prevents the emergence of weed seedlings, or the weeds grow until they reach the cotyledon stage, but then they stop growing and eventually die completely after three to four weeks.

[0131] If the active ingredient is applied to the green parts of the plant after emergence, growth will stop after treatment, and harmful plants will remain at the growth stage at the time of application or die completely after a certain period of time, thus eliminating competition from harmful weeds for the crop plant early and in a continuous manner.

[0132] The herbicidal product of this invention is distinguished by its rapid onset of action and long-lasting weed control. Generally, the rain resistance of the active ingredients in the compound of this invention is advantageous. A particular advantage is that the effective dosage of compounds (a) and (b) used in the compound can be adjusted to levels as low as optimal for their soil action. Therefore, it can be used not only on sensitive crops but also effectively prevents groundwater contamination. The compound of the active ingredients of this invention allows for a significant reduction in the required application amount of the active ingredients.

[0133] The combined use of herbicides (a) and (b) yields performance characteristics that exceed those expected based on the known properties of the individual herbicides used in the combination. For example, the weed control effect against a particular harmful plant species exceeds the expected value that could be estimated using standard methods (e.g., according to Colby or other extrapolation methods).

[0134] A synergistic effect exists when the effect of the active ingredient combination (herbicidal effect in this paper) is greater than the sum of the effects of the active ingredients applied alone. The expected activity of a given combination of two active ingredients can be determined according to SRColby (“Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds). 15 (1967), 20-22 (see below) calculation.

[0135] Therefore, synergistic effects allow for, for example, reduced application of individual active ingredients, higher efficacy at the same application rate, control of previously uncovered (blank) harmful plant species, increased residual activity, extended efficacy period, increased rate of action, extended application period and / or reduced number of individual applications required, and the result for users is a more economically and ecologically advantageous weed control system.

[0136] Although the compounds of the present invention exhibit excellent herbicidal activity against both monocot and dicot weeds, many economically important crops suffer only negligible damage (if any) depending on the structure of the corresponding active ingredient compounds and the amount applied. Here, economically important crops include, for example, dicotyledonous crops from genera such as *Peanuta*, *Begonia*, *Brassica*, *Cucumis*, *Cuburbita*, *Helianthus*, *Carrot*, *Soybean*, *Cotton*, *Ipomoea*, *Lactuca*, *Flavorula*, *Tomato*, *Tobacco*, *Phaseolus*, *Vaccinium*, *Solanum*, and *Fava*, or monocotyledonous crops from genera such as *Allium*, *Pineapple*, *Asparagus*, *Oats*, *Barley*, *Rice*, *Sorghum*, *Sugarcane*, *Rye*, *Sorghum*, *Triticum*, *Wheat*, and *Zea*.

[0137] Furthermore, the compounds / compositions of the present invention exhibit prominent growth-regulating properties in crop plants under certain conditions. They intervene in the plant's own metabolism through regulatory effects and can therefore be used for controlled influence on plant components and to promote harvest, for example, by inducing dehydration and dwarfing growth. In addition, they are suitable for the comprehensive control and suppression of unwanted vegetative growth without killing the plant in the process. Suppression of vegetative growth is crucial for many monocotyledonous and dicotyledonous crops because it reduces or completely prevents lodging.

[0138] Due to their weed-controlling and plant growth-regulating properties, these conjugates / compositions can be used to control harmful plants in known or yet-to-be-developed resistant crop plants, whether through conventional mutagenesis or genetic engineering. Generally, transgenic plants, in addition to resistance to the conjugates / compositions of this invention, possess other specific advantageous characteristics, such as resistance to plant diseases or organisms that cause plant diseases (e.g., certain insects or microorganisms such as fungi, bacteria, or viruses). These other specific characteristics relate to, for example, the quantity, quality, storability, conjugate / composition, and specific components of the harvest. For example, transgenic plants are known to have increased starch content or altered starch quality, or those with different fatty acid combinations / compositions in their harvests. Other specific characteristics may include tolerance or resistance to abiotic stresses such as heat, low temperature, drought, salinity, and ultraviolet radiation.

[0139] Preferably, the active ingredient conjugate of the present invention can be a herbicide from a plant crop that is resistant to the phytotoxic effects of the herbicide or has been genetically engineered to be resistant to the phytotoxic effects of the herbicide.

[0140] Preferably, the active ingredient conjugate of the present invention can be used in genetically modified crops that are resistant to or have been conferred resistance to the active ingredient used.

[0141] Preferably, the active ingredient conjugate of the present invention can also be used in herbicides that inhibit growth regulators (e.g., dicamba) or essential plant enzymes (e.g., acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS), or hydroxyphenylpyruvate dioxygenase (HPPD)), or in transgenic crops resistant to herbicides derived from sulfonylureas, glyphosate, glufosinate, or benzoylisoxazoles and similar active ingredients.

[0142] Therefore, the present invention also provides a method for preventing unwanted plant growth, optionally in crop plants, preferably on uncultivated land or in plantation crops, characterized by applying one or more types (a) of herbicides together with one or more types (b) of herbicides to the harmful plant, parts of the plant or plant seeds, or to the growing area.

[0143] The present invention also provides the use of novel combinations of compounds (a)+(b) for the control of harmful plants, optionally in crop plants, preferably in uncultivated land and plantation crops, but also for the control of harmful plants before the sowing of subsequent crop plants, for example, particularly for sowing preparation (“non-selective application”).

[0144] The active ingredient complex of the present invention may exist as a mixture of the two components, if appropriate, with other active ingredients, additives and / or common formulation adjuvants, which is then applied by diluting with water in a conventional manner, or may be prepared as a so-called tank mix by co-diluting separately or partially separately formulated components with water.

[0145] Compounds (a) and (b) or combinations thereof, or combinations thereof, can be formulated in a variety of ways depending on the desired biological and / or physicochemical parameters. Examples of general formulations that may be selected include: wettable powders (WP), water-soluble powders (SP), emulsifiable concentrates (EC), water-soluble concentrates, aqueous solutions (SL), emulsions (EW) such as oil-in-water emulsions and water-in-oil emulsions, sprayable solutions or emulsions, oil-based or water-based dispersants, oil dispersants (OD), suspension emulsions, suspension concentrates (SC), oil-miscible solutions, microcapsule suspensions (CS), dusting products (DP), seed dressings, granules for soil application or broadcasting, granules in microgranular form (GR), sprayable granules, absorbent and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, or waxes.

[0146] Therefore, the present invention also provides herbicidal compositions and plant growth regulating compositions comprising the active ingredient complex of the present invention.

[0147] The types of each formulation are known in principle and described in, for example, the following literature: Winnacker-Küchler, "Chemische Technologie" [Chemical technology], Vol. 7, C. Hanser Verlag Munich, 4th edition, 1986; van Valkenburg, "Pesticides Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd edition, 1979, G. Goodwin Ltd. London.

[0148] The required formulation adjuvants, such as inert substances, surfactants, solvents, and other additives, are also known and described in, for example, the following literature: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ; Hv Olphen, "Introduction to Clay Colloid Chemistry"; 2nd ed., J. Wiley & Sons, NY Marsden; "Solvents Guide", 2nd ed., Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte" ["Interface-active EthyleneOxide Adducts"], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th edition, 1986.

[0149] Based on these formulations, compounds can also be prepared with other pesticide active substances (such as other herbicides, fungicides, insecticides or other pesticides (such as acaricides, nematicides, molluscicides, rodenticides, aphicides, birdicides, larvicides, ovicides, bactericides, viricides, etc.) and with fertilizers and / or growth regulators, for example in the form of finished formulations or tank mixes.

[0150] Wettable powders are formulations that can be uniformly dispersed in water. In addition to the active ingredient and diluents or inert substances, they contain ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyethylene glycol ether sulfates, alkyl sulfonates, alkylbenzene sulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl taurate. To prepare wettable powders, the herbicidal active ingredient is finely ground, for example, in conventional equipment such as a hammer mill, air mill, or air jet mill, and mixed simultaneously or subsequently with formulation adjuvants.

[0151] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (such as butanol, cyclohexanone, dimethylformamide, xylene, or relatively high-boiling aromatic compounds or hydrocarbons) or a mixture of organic solvents, and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium alkyl aryl sulfonates, such as calcium dodecylbenzene sulfonate; or nonionic emulsifiers, such as fatty acid polyethylene glycol esters, alkyl aryl polyethylene glycol ethers, fatty alcohol polyethylene glycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, and sorbitol esters (e.g., sorbitol fatty acid esters, or polyoxyethylene sorbitol fatty acid esters).

[0152] Powdered products are obtained by grinding the active ingredients together with finely dispersed solids such as talc, natural clays (such as kaolin, bentonite, and pyrophyllite) or diatomaceous earth.

[0153] The suspension concentrate can be water-based or oil-based. It can be prepared by, for example, wet milling using a commercially available bead mill and optionally by adding surfactants listed above (e.g., for other types of formulations).

[0154] Emulsions, such as oil-in-water emulsions (EW), can be prepared using, for example, agitators, colloid mills and / or static mixers, with aqueous organic solvents and optional surfactants as listed above (e.g. for other types of formulations).

[0155] Granules can be prepared by spraying the active ingredient onto an absorbent granular inert material or by applying a concentrated active ingredient to the surface of a carrier material (such as sand, kaolinite, or granular inert material) using an adhesive (such as polyvinyl alcohol, sodium polyacrylate, or mineral oil). Alternatively, suitable active ingredients can be granulated using conventional methods for preparing fertilizer granules—if necessary, by mixing them with fertilizer.

[0156] Water-dispersible granules are typically prepared by methods such as spray drying, fluidized bed granulation, disc granulation, mixing with a high-speed mixer, and extrusion without solid inert substances.

[0157] Agricultural chemical formulations typically contain 0.1% to 99% by weight, particularly 0.2% to 95% by weight, of class (a) and / or (b) active ingredients. The following concentrations are standard concentrations based on the formulation type: In wettable powders, the concentration of the active ingredient is, for example, from about 10% to 95% by weight; the balance, up to 100% by weight, consists of conventional formulation ingredients. In the case of emulsifiable concentrates, the concentration of the active ingredient can be from about 1% to 90% by weight, preferably from 5% to 80% by weight.

[0158] Powder formulations typically contain 5% to 20% by weight of the active ingredient; sprayable solutions contain about 0.05% to 80%, preferably 2% to 50% by weight of the active ingredient.

[0159] In the case of granules, such as dispersible granules, the content of the active ingredient depends in part on whether the active compound is in liquid or solid form and what granulation aids and fillers are used. Typically, in water-dispersible granules, the content of the active ingredient is from 1% to 95% by weight, preferably from 10% to 80% by weight.

[0160] In addition, the active ingredient formulations mentioned may optionally include corresponding conventional adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, colorants and carriers, defoamers, evaporation inhibitors, and pH adjusters or viscosity adjusters.

[0161] For application, commercially available formulations should be diluted in a conventional manner, if appropriate, such as with water in the case of wettable powders, emulsifiable concentrates, dispersants, and water-dispersible granules. Powder formulations, granules for soil application or broadcasting, and sprayable solutions are generally not further diluted with other inert substances before application.

[0162] The active ingredient can be applied to plants, plant parts, plant seeds or planting areas (soil), preferably to green plants and plant parts, and optionally additionally to the soil.

[0163] One possible method of use is to apply the active ingredients together in the form of a tank mix, in which the optimal formulations of the individual active ingredients are mixed together with water in a tank, and then the resulting spray is applied.

[0164] Because the amounts of the components have been adjusted to the correct proportions, the combined herbicidal formulation of the active ingredients (a) and (b) of this invention has the advantage of being easier to apply. Furthermore, the adjuvants in the formulation can be optimally adjusted to each other; however, tank mixing of different formulations may result in unwanted combinations of adjuvants.

[0165] General testing methods: Mixed materials in buckets; after emergence A) Method Description Crop seeds (spring wheat, TRZAS; spring barley, HORVS; maize, ZEAMA) were sown in peat pots filled with sandy loam, covered with soil, and cultivated in a greenhouse under favorable growing conditions. Two to three weeks after sowing, test plants at the 1- to 3-leaf stage were treated. The herbicide / safener active compound combination according to the invention was formulated as a wettable powder or emulsion concentrate, and in parallel trials, the correspondingly formulated single active compounds were sprayed at different doses onto the green parts of the plants using 300 l / ha (converted).

[0166] Return the pots to the greenhouse and place them under good growing conditions. Visually assess the weed control effect at intervals of 1 to 3 weeks after herbicide application (DAT = days after treatment). Evaluations are expressed as a percentage and compared to untreated control plants (0% = no damage, 100% = complete death).

[0167] The effects of the safety agent treatment are shown below: The reduction value [difference] = Damage caused by herbicides without safeners - Damage caused by herbicides with safeners; Reduction rate [%] = (Reduction value [Difference]) 100) / Damage caused by herbicides without safener 1 day before treatment A) Method Description Crop seeds (spring wheat, TRZAS; spring barley, HORVS; maize, ZEAMA) were sown in pots 7-8 mm in diameter filled with sandy loam, covered with soil, and cultivated in a greenhouse under favorable growing conditions until the plants reached the 1-3 leaf stage (BBCH 11-13). For treatments involving multiple applications of the safener and herbicide, the safener was applied first, followed by the herbicide the next day. The safener and herbicide were formulated as a wettable powder (WP) and sprayed as an aqueous suspension onto the green parts of the plants at a rate equivalent to 300 l / ha of water, with the addition of wetting agents and adjuvants (e.g., Mero, 1.5 l / ha; ammonium sulfate, 2 kg / ha). A group of equivalent plants were treated with the herbicide only, without prior treatment with the safener.

[0168] Following application, the test plants were kept in a greenhouse under favorable growing conditions. On days 10 and 21 (DAT) after herbicide treatment, the percentage of crop damage observed on the treated plants was assessed visually by comparison with control plants that had not received any safener or herbicide treatment.

[0169] The effects of the safety agent treatment are shown below: The reduction value [difference] = Damage caused by herbicides without safeners - Damage caused by herbicides with safeners; Reduction rate [%] = (Reduction value [Difference]) 100) / Damage caused by herbicides without safener Seed treatment; pre-emergence A) Method Description For seeds treated with safeners, weigh a sufficient amount of the corresponding crop (spring wheat, TRZAS; spring barley, HORVS; corn, ZEAMA) and place it in a screw-cap glass bottle with a volume approximately twice that of the seeds.

[0170] Weigh out the specific safety agent prepared as a wettable powder (WP) to the prescribed dosage (g ai / kg seeds), dissolve it in water (1 ml water for every 10 g seeds), and then add it to the seeds to make a slurry.

[0171] After sealing the bottle, place it in a top-mounted shaker (shake at medium speed for about 60 minutes) to ensure the seeds are evenly coated with the slurry. After opening the bottle, let the seeds air dry on paper for 3-4 hours before sowing, or sow them directly. Place the seeds in a 7-8mm diameter pot filled with sandy loam soil and cover with soil.

[0172] Subsequently, the two groups of plants were treated with the specified herbicide before emergence: a) Treat the seeds with a safener as described above; b) No safety agent was used.

[0173] The herbicide is formulated as WP and sprayed onto the soil surface in the form of an aqueous suspension at a water application rate equivalent to 300 l / ha.

[0174] Following application, test plants were kept in a greenhouse under favorable growing conditions. The percentage of crop damage observed on treated plants was assessed visually at intervals of up to 4 weeks (= 28 days post-treatment; DTA) by comparison with control plants that had not received any safener or herbicide treatment.

[0175] The values ​​in the table below are averages of at least two replicates.

[0176] The effects of the safety agent treatment are shown below: The reduction value [difference] = Damage caused by herbicides without safeners - Damage caused by herbicides with safeners; Reduction rate [%] = (Reduction value [Difference]) 100) / Damage caused by herbicides without safener Seed treatment; after emergence A) Method Description For seeds treated with safeners, weigh a sufficient amount of the corresponding crop (spring wheat, TRZAS; spring barley, HORVS; corn, ZEAMA) and place it in a screw-cap glass bottle with a volume approximately twice that of the seeds.

[0177] Weigh out the specific safety agent prepared as a wettable powder (WP) to the prescribed dosage (g ai / kg seeds), dissolve it in water (1 ml water for every 10 g seeds), and then add it to the seeds to make a slurry.

[0178] After sealing the bottle, place it in a top-mounted shaker (shake at medium speed for about 60 minutes) to ensure the seeds are evenly coated with the slurry. After opening the bottle, let the seeds air dry on paper for 3-4 hours before sowing, or sow them directly. Place the seeds in a 7-8mm diameter pot filled with sandy loam soil, cover with soil, and cultivate in a greenhouse under favorable growing conditions.

[0179] When the plants reached the BBCH11-13 growth stage, both groups of plants were treated post-emergence with the specified herbicide: a) Treat the seeds with a safener as described above; b) No safety agent was used.

[0180] The herbicide is formulated as WP and sprayed as an aqueous suspension onto the green parts of the plant at a rate equivalent to 300 l / ha of water, with added wetting agents and adjuvants (e.g., Mero, 1.5 l / ha; ammonium sulfate, 2 kg / ha).

[0181] Following application, the test plants were kept in a greenhouse under favorable growing conditions. On days 10 and 21 (DAT) after herbicide treatment, the percentage of crop damage observed on the treated plants was assessed visually by comparison with control plants that had not received any safener or herbicide treatment.

[0182] The values ​​in the table below are averages from at least two replicates. The effects of the safety agent treatment are represented as follows: The reduction value [difference] = Damage caused by herbicides without safeners - Damage caused by herbicides with safeners; Reduction rate [%] = (Reduction value [Difference]) 100) / Damage caused by herbicides without safener Test of compounds according to the present invention A. Formulation Examples a) The powdered product is obtained by mixing 10 parts by weight of active ingredient (a) or (b), or a mixture of active ingredients (a) + (b) (and optional additional active ingredient components) and / or their salts with 90 parts by weight of talc as an inert substance and pulverizing in an impact mill.

[0183] b) A wettable powder that is easily dispersible in water is obtained by mixing 25 parts by weight of active ingredient / active ingredient mixture, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignin sulfonate and 1 part by weight of sodium oleoylmethyl taurate as a wetting agent and dispersant, and grinding the mixture in a pin mill.

[0184] c) A water-dispersible concentrate is obtained by mixing 20 parts by weight of the active ingredient / active ingredient mixture with 6 parts by weight of alkylphenol polyethylene glycol ether (Triton® X 207), 3 parts by weight of isotridecyl polyethylene glycol ether (8EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to 277 °C), and grinding the mixture in a ball mill to a fineness of less than 5 microns.

[0185] d) The emulsifiable concentrate is obtained by mixing 15 parts by weight of active ingredient / active ingredient mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.

[0186] e) Water-dispersible granules are obtained in the following ways: Mix the following substances: 75 parts by weight of active ingredient / active ingredient mixture, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol, and 7 parts by weight of kaolin; The resulting mixture was ground in a pin mill and the powder was granulated in a fluidized bed by spraying water, which was applied as a granulation liquid.

[0187] f) Water-dispersible granules can also be obtained in the following ways: The following materials were homogenized and pre-pulverized in a colloid mill: 25 parts by weight of active ingredient / active ingredient mixture, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate 2 parts by weight of sodium oleoylmethyl taurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate, and 50 parts by weight of water; The mixture is then ground in a ball mill, and the resulting suspension is atomized and dried in a spray tower through a single-phase nozzle.

[0188] B. Biological Examples When using the combinations of the present invention, it is frequently observed that their weed-controlling effect on harmful plant species exceeds the sum of the effects of existing herbicides when applied alone. Alternatively, in some cases, it can be observed that a smaller application amount of the herbicide combination is required to achieve the same effect on harmful plant species compared to individual formulations. Such enhanced action, increased efficacy, or reduced application amount are all strong indicators of synergistic effects.

[0189] When the observed efficacy exceeds the sum of the formal values ​​of the individual administrations, it also exceeds the expected value calculated by Colby using the following formula, and this is also considered an indicator of synergistic effect (see SR Colby; in Weeds 15 (1967), pp. 20–22): E C = A + B - (A·B / 100) in A = The efficacy of active ingredient (a) at an application rate of a [g ai / ha], expressed as a percentage; B = The efficacy of active ingredient (b) at an application rate of b [g ai / ha], expressed as a percentage. E C =The expected effect of the combination (a)+(b) at a combined application rate of a+b [g ai / ha], expressed as a percentage.

[0190] At a given suitable low dose, the observed values ​​from the experiment (E) A This indicates that the effect of the conjugate exceeded Colby's expected value (E). C ) (Δ).

[0191] 1. Post-emergence effects on weeds (Method 1 - based on the data shown in Table 4) Seeds or rhizome segments of monocotyledonous and dicotyledonous weeds were placed in pots filled with sandy loam, covered with soil, and grown in a greenhouse under favorable growing conditions (temperature, air humidity, water supply). Approximately three weeks after sowing, at the three-leaf stage, test plants were treated with the combination / composition of the present invention. The composition / composition of the present invention, prepared as a spray powder or emulsion concentrate, was sprayed onto the green plant parts at various dosages, equivalent to an application rate of 300 to 800 l / ha of water. After the test plants were grown in a greenhouse under optimal growing conditions for approximately 2 to 4 weeks, the effect of the treatment was evaluated visually by comparison with an untreated control group. The combination / composition of the present invention also exhibits good post-emergence weed control activity against a broad spectrum of economically important weeds and broadleaf weeds.

[0192] It is frequently observed here that the effects of the combination of the present invention exceed the sum of the effects of applying the herbicide alone. At suitable low doses, observations from experiments indicate that the effects of the combination exceed Colby's expectations.

[0193] 2. Herbicidal effect before and after emergence (field trial) The experiment was conducted outdoors, following the greenhouse experiment described in Section 1. The evaluation method was similar to that used in Section 1.

[0194] 3. Herbicidal effect and crop-plant compatibility (field trials) Crop plants are planted on outdoor plots under natural outdoor conditions, while seeds or rhizomes of typical harmful plants are planted or natural weed communities are utilized. Treatment with the combination / composition of the present invention is carried out after the harmful plants and crop plants have emerged, generally at the 2- to 4-leaf stage; in some cases (as specified), pre-emergence application or treatment in a partially pre-emergence and / or post-emergence sequence is performed using the individual active ingredient or active ingredient combination.

[0195] In the case of plantation crops, the soil between the individual crop plants is usually treated only with active ingredients.

[0196] Following application, for example at 2, 4, 6, and 8 weeks, the efficacy of the herbicide was evaluated visually by comparison with an untreated control. The conjugates / compositions of the present invention also exhibited synergistic herbicidal activity against a broad spectrum of economically important weeds and broadleaf weeds in field trials. Comparisons showed that the conjugates of the present invention generally had a greater, and in some cases significantly greater, herbicidal effect than the sum of the effects of individual herbicides, thus demonstrating synergy. For most of the evaluation period, the effect was also higher than expected according to Colby, thus again demonstrating synergy. In contrast, as a result of treatment with the herbicide, crop plants suffered only negligible damage (if any).

[0197] 4. Definitions in the embodiments The following abbreviations were used in the subsequent descriptions and tables: g ai / ha = grams of active substance (active ingredient) per hectare (=100% active compound); The sum of the effects of individual applications is expressed in E A Record; Based on Colby's expected value, respectively using E C Record.

[0198] Biological results of the conjugates / compositions according to the present invention are summarized in Table 4. Evaluation periods were recorded in days after administration (DTA).

[0199] Table 4 shows the synergistic effect (Δ) of a herbicidal binary conjugate comprising (a) a substituted isoxazoline-formamide of formula (I) 1.68 and (b) one of B1 to B35, applied to weeds after emergence (see Method 1 above).

[0200] Select the following weeds for testing (see Table 3): Table 3 Table 4

Claims

1. A complex, comprising (a) A substituted isoxazoline-formamide of formula (I) or an agrochemically acceptable salt thereof (I) in G stands for OR 4 or NR 7 R 8 ; R 1 and R 2 Each represents hydrogen; R 3 Represents (C1-C5)-alkyl, (C3-C6)-cycloalkyl, (C2-C5)-alkenyl, (C2-C5)-alkynyl or (C1-C5)-alkoxy, each optionally substituted "m" times with a substituent selected from halogen, cyano, (C1-C5)-alkoxy and hydroxyl; R 4 Represents hydrogen, or Representative (C1-C) 12 (C3-C7)-alkyl, (C3-C7)-cycloalkyl-(C1-C8)-alkyl, (C2-C8)-alkenyl, (C5-C6)-cycloalkenyl, (C1-C4)-alkylphenyl or (C2-C8)-ynyl, each optionally selected from halogen, cyano, (C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl, hydroxyl, S(O) n R 5 The substituents are replaced "m" times; R 5 Represents (C1-C8)-alkyl, (C2-C8)-alkenyl, (C3-C6)-cycloalkyl, benzyl, CON((C1-C3)-alkyl)2 or (C1-C8)-alkyl-C(O)-(C1-C8)-alkyl, each of which may optionally be substituted "m" times with a substituent selected from halogens and cyano groups; R 6 Represents hydrogen, or Represents (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C3-C8)-alkenyl or (C3-C8)-alkynyl, each optionally substituted "m" times by a substituent selected from halogen, cyano and (C1-C2)-alkoxy; R 7 R 8 Each of these independently represents hydrogen, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl, N((C1-C3)-alkyl)2, and S(O). n R 5 ; or R 7 and R 8 Together with the nitrogen atoms they are attached to, they form saturated or partially or completely unsaturated five-, six-, or seven-membered rings. In addition to nitrogen atoms, these rings may contain "r" carbon atoms and "o" oxygen atoms, and are optionally selected from halogens, (C1-C6)-alkyl groups, halogen-(C1-C6)-alkyl groups, oxo groups, and CO2R groups. 6 The substituents are replaced "m" times; Z represents Z-1 to Z-8: The arrows represent bonds to the CO-G groups in formula (I); X 2 X 4 and X 6 Each can represent either hydrogen or fluorine independently; X 3 and X 5 Each can independently represent hydrogen, chlorine, cyanide, or fluorine; or Represents (C1-C3)-alkyl, (C1-C3)-alkoxy, each optionally substituted "m" times with a substituent selected from fluorine or chlorine; m represents 0, 1, 2, 3, 4 or 5; n represents 0, 1, or 2; o represents 0, 1, or 2; r represents 3, 4, 5, or 6; and (b) One or more of B1 to B35 specified in Table 1 below: Table 1 。 2. The combination according to claim 1, characterized in that, Compound (I) is a chemically acceptable salt of formula (Ia) or an agrochemically acceptable salt thereof. (him) in X 3 X 5 R 3 And G as described above; Z represents Z-1a, Z-1b,, Z-2a, Z-3a, Z-4a,, Z-5a, Z-6a, Z-7a,, Z-8a, Where Z-4a represents a mixture of structures Z-4b and Z-4c; Furthermore, Z-8a represents a mixture of structures Z-8b and Z-8c. Furthermore, the arrows indicate the bonding with the CO-G group in formula (Ia).

3. The combination according to claim 2, characterized in that, Compounds of formula (Ia) or their agrochemically acceptable salts have the following definitions. X 3 For F; X 5 For F; R 3 It is (S)-vinyl; -ZC(O)-G- is , Z-4a is .

4. The combination according to any one of claims 1 to 3, wherein the amount of herbicide applied is from 0.1 to 500 g ai / ha.

5. The combination according to any one of claims 1 to 3, wherein the amount of herbicide applied is 1.0 to 250 g ai / ha.

6. The combination according to any one of claims 1 to 5, wherein the weight ratio of active ingredient components (a) and (b) is from 1:10000 to 5000:

1.

7. The combination according to any one of claims 1 to 5, wherein the weight ratio of active ingredient components (a) and (b) is 1:1000 to 500:

1.

8. The combination according to any one of claims 1 to 5, wherein the weight ratio of active ingredient components (a) and (b) is from 1:100 to 50:

1.

9. The combination according to any one of claims 1 to 5, wherein the weight ratio of active ingredient components (a) and (b) is from 1:10 to 5:

1.

10. A herbicidal composition comprising a herbicidal compound according to any one of claims 1 to 9 and one or more other components, said other components being selected from formulation adjuvants, additives commonly used in crop protection, and other agrochemically active compounds, such as fungicides, insecticides, acaricides, etc.

11. Methods for controlling harmful plants or regulating plant growth, including, The active ingredient component of the herbicidal compound according to any one of claims 1 to 9 or the herbicidal composition according to claim 10 is applied to plants, plant parts, plant seeds or planting areas.

12. The method according to claim 11, wherein, The active ingredient component of the herbicidal compound according to any one of claims 1 to 9 or the herbicidal composition according to claim 10 is applied to the plant, plant parts, plant seeds or planting area by pre-emergence method, post-emergence method or pre-emergence and post-emergence method, or together or separately.

13. The method according to any one of claims 11 to 12, wherein the crop is a genetically modified plant.

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