Selective herbicides based on substituted isoxazoline carboxamides and flirazoles

Abstract

The problem that this invention aims to solve is to provide a selective herbicide that effectively prevents damage to crop plants and selectively controls weeds in many types of useful plants, such as grains and corn. [Solution] The present invention relates to a novel combination of selective herbicidal compounds comprising a substituted isoxazoline carboxamide or a pesticide-acceptable salt thereof and flirazole, which can be used with particularly good results for the selective control of weeds in various crops of useful plants.

Description

[Technical Field]

[0001] The present invention relates to a novel combination of selective herbicidal compounds comprising a substituted isoxazoline carboxamide or a pesticide-acceptable salt thereof and flirazole, which can be used with particularly good results for the selective control of weeds in various crops of useful plants. [Background technology]

[0002] Substituted isoxazoline carboxamides are already known as effective herbicides from International Publication Nos. 2018 / 228985 and International Publication Nos. 2019 / 145245. However, the activity and / or compatibility of these compounds with crop plants are not entirely satisfactory under all conditions.

[0003] Frillazole (IUPAC: 3-(dichloroacetyl)-5-(2-furanyl)-2,2-dimethyl-oxazolidine; CAS: 121776-33-8) is a drug-induced harm reduction agent known from European Patent No. 0304409. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2018 / 228985 Brochure [Patent Document 2] International Publication No. 2019 / 145245 brochure [Patent Document 3] European Patent No. 0304409 [Overview of the Initiative]

[0005] Surprisingly, it has now been found that certain substituted isoxazoline carboxamides, when used together with the furalazoles described below, very effectively prevent damage to crop plants and can be used particularly advantageously as a broad-spectrum combination preparation for the selective control of weeds (= unwanted plants) in crops of useful plants such as cereals and maize.

Means for Solving the Problems

[0006] The present invention relates to (a) a substituted isoxazoline carboxamide of formula (I) or a pesticidally acceptable salt thereof

Chemical formula

Chemical formula

[0007] Definition Halogen represents the radicals of fluorine, chlorine, bromine and iodine. Preferred are the radicals of fluorine and chlorine.

[0008] Alkyl is a saturated straight-chain or branched hydrocarbyl radical having the number of carbon atoms specified in each case, for example 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, 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, etc. C1-C6-alkyl. <了

[0009] Note: There is a possible error in the original text where "r represents 3, 4, ⑤ or 6)" has an incorrect character "⑤". It should probably be "5". The translation is done based on the provided text as accurately as possible.Alkenyls are unsaturated linear or branched hydrocarbyl radicals having a specified number of carbon atoms in each case and one double bond at any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl L, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4- Methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl , 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,This refers to C2-C6 alkenyls such as 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl.

[0010] Alkynyl represents a linear or branched hydrocarbyl group having 2 to 8, preferably 2 to 6, carbon atoms and one triple bond at any position. Examples that are not limited to these include ethinyl, propa-1-inyl, propa-2-inyl, buta-1-inyl, buta-2-inyl, buta-3-inyl, 1-methylpropa-2-inyl, penta-1-inyl, penta-2-inyl, penta-3-inyl, penta-4-inyl, 1-methylbuta-2-inyl, 1-methylbuta-3-inyl, 2-methylbuta-3-inyl, 3-methylbuta-1-inyl, 1,1-dimethylpropa-2-inyl, 1-ethylpropa-2-inyl, hexa-1-inyl, hexa-2-inyl, hexa-3-inyl, hexa-4-inyl, hexa-5-inyl, 1-methylpenta-2-inyl, 1 Examples include methylpenta-3-inyl, 1-methylpenta-4-inyl, 2-methylpenta-3-inyl, 2-methylpenta-4-inyl, 3-methylpenta-1-inyl, 3-methylpenta-4-inyl, 4-methylpenta-1-inyl, 4-methylpenta-2-inyl, 1,1-dimethylbuta-2-inyl, 1,1-dimethylbuta-3-inyl, 1,2-dimethylbuta-3-inyl, 2,2-dimethylbuta-3-inyl, 3,3-dimethylbuta-1-inyl, 1-ethylbuta-2-inyl, 1-ethylbuta-3-inyl, 2-ethylbuta-3-inyl, and 1-ethyl-1-methylpropa-2-inyl.

[0011] Cycloalkyl refers to a carbocyclic saturated ring system preferably having 3 to 8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. In the case of substituted cycloalkyls, this may include ring systems with substituents, including substituents having a double bond on the cycloalkyl group, such as alkylidene groups like methylidene.

[0012] Alkoxy is a saturated linear or branched alkoxy group having the number of carbon atoms specified in each case, such as 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, 1,2-dimethylpropoxy, 1-methylpentoxy, 2- This refers to C1-C6 alkoxys such as 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 means a C1-C2 haloalkoxy having the number of carbon atoms specified in each case, where some or all of the hydrogen atoms of these groups may be replaced by the halogen atoms specified above, 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-trifluoropropa-2-oxy. [Modes for carrying out the invention]

[0013] The compounds according to the present invention are generally defined by formula (I). Preferred substituents or ranges for the groups given by the above and below formulas are shown below:

[0014] A preferred combination of herbicides is one of the compounds of formula (Ia) or a pesticide-acceptable salt thereof. [ka] In the above equation, X 3 , X 5 , R 3 And G is as stated above; Z is Z-1a, Z-1b, Z-2a, Z-3a, Z-4a, Z-5a, Z-6a, Z-7a, Z-8a [ka] Meaning, In the above equation, Z-4a is a mixture of both structures Z-4b and Z-4c. [ka] Meaning; Z-8a is a mixture of structures Z-8b and Z-8c. [ka] Meaning; The arrows indicate bonding to the group CO-G in equation (Ia).

[0015] Particularly preferred are combinations of herbicides in which the compound of formula (Ia) is one of the compounds in Table 1 or a pesticide-acceptable salt thereof. [ka]

[0016] [Table 1A] [Table 1B] [Table 1C] [Table 1D] [Table 1E] [Table 1F] [Table 1G] [Table 1H]

[0017] Surprisingly, it has now been found that the combination of the above-defined active compounds of substituted isoxazoline carboxamides of general formula (I) and / or their salts with flirazole is very well tolerated by crop plants, while possessing particularly high herbicidal activity, and can be used for selective control of weeds (= undesirable plants) in a variety of crops, especially cereals (particularly wheat and barley) and maize, as well as in soybeans, potatoes and rice.

[0018] Here, it must be considered remarkable that, among the many known phytotoxicity reducers or antidotes capable of antagonizing the damaging effects of herbicides on crop plants, flurazole substantially completely neutralizes the damaging effects of substituted isoxazoline carboxamide on crop plants without adversely affecting its herbicidal activity against weeds.

[0019] Here, the particularly advantageous effects of flirazole are highlighted, especially in relation to the preservation of cereal plants such as wheat, barley, and rye, as well as crop plants such as maize and rice.

[0020] The combination of active compounds according to the present invention can be used, for example, in relation to the following plants:

[0021] Dicotyledonous weeds of the following genera: Synapse, Lepidium, Galium, Chickweed, Chrysanthemum, Roman Chamomile, Chrysanthemum, Cenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthum, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Thistle, Cirsium, Sonkus, Solanum, Rorippa indica, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Lamium amplexicaule, Papaver, Centaurea, Trifolium, Ranunculus, and Dandelion.

[0022] Dicotyledonous crops of the following genera: Cotton, Soybean, Betta, Carrot, Bean, Pea, Solanum, Flax, Sweet Potato, Broad Bean, Tobacco, Tomato, Peanut, Brassica, Lactuca, Cucumis, Pumpkin (Cuburbita), Sunflower.

[0023] Monocotyledonous weeds of the following genera: Echinocloa, Setaria, Panicum, Digitalia, Fleurum, Poa, Festuca, Eleuthine, Velvet Grass, Lorium, Brassica, Avena, Cyperus, Sorghum, Agropylon, Magnolia, Monocoria, Sagittaria, Eleocharis, Scurbulus, Barnyard Grass, Platypus, Euphorbia, Grass, Agrostis, Alopeculus, and Psocoptera.

[0024] Monocotyledonous crops of the following genera: rice, maize, wheat, barley, oats, rye, sorghum, millet, sugarcane, pineapple, asparagus, and onion.

[0025] However, the use of the combination of active compounds according to the present invention is by no means limited to these genera, but is similarly extended to other plants. According to the present invention, crop plants include all plants and plant varieties, including transgenic plants and plant varieties, and synergistic effects may occur in transgenic plants and plant varieties.

[0026] The present invention further relates to a method for reducing crop damage by treating crop seeds with a phytotoxicity reducer before sowing. This can be done in addition to using herbicide / phytotoxicity reducer combinations and compositions thereof that are highly suitable for protecting crops from herbicide damage during pre-germination and post-germination treatment.

[0027] The object of the present invention was to provide a method for further reducing crop damage using known combinations of herbicides and phytotoxicity reducers and compositions containing them. Surprisingly, this object is achieved by the following treatment method / scheme. Method A Step 1: Seed treatment with Frizol Step 2: Application of compound (I) or a composition containing it in post-emergence treatment. Method B Step 1: Seed treatment with Frizol Step 2: Application of compound (I) or a composition containing it in pre-budding treatment. The preferred method is as follows: Method Aa Step 1: Seed treatment with Frizol Step 2: Application of compound (Ia) or a composition containing it in post-emergence treatment. Method Ba Step 1: Seed treatment with Frizol Step 2: Application of compound (Ia) or a composition containing it in pre-budding treatment.

[0028] seed: For example, seeds of various grains (wheat, rye, barley, rye), corn, maize, and other crop plants.

[0029] composition A composition within the context of the present invention comprises one or more additional components in addition to the herbicide / phytotoxicity reducer combination according to the present invention. These components include, but are not limited to, formulation aids, additives commonly used in crop protection, and further pesticide-active compounds (e.g., fungicides and insecticides).

[0030] additives Additives include, for example, fertilizers and colorants.

[0031] Method 1: Until the day before The present invention further relates to a method for reducing crop damage by pre-incubating crops with a phytotoxicity reducer for 24 hours before applying the herbicide or a combination / composition of herbicides / phytotoxicity reducers.

[0032] In another embodiment, the present invention relates to a combination of selective herbicides comprising at least one further herbicide (c), wherein (c) is selected from, but is not limited to, the following:

[0033] Acetochlor, aciflorphen, aciflorphen-methyl, aciflorphen-sodium, acroniphen, alachlor, alidoclor, alloxidim, alloxidim-sodium, ametrine, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralide, aminopyralide-dimethylammonium, aminopyralide-tripromine, amitorol, ammonium sulfamate, anirophos, ashram, ashram-potassium, ashram-sodium, atrazine, azaphenidine, azimsulfuron, beflubutamide,(S)-(-)-Beflubutamide, Beflubutamide-M, Benazoline, Benazoline-ethyl, Benazoline-dimethylammonium, Benazoline-potassium, Benfluralin, Benfresate, Bensulfuron, Bensulfuron-methyl, Benslid, Bentazone, Bentazone-sodium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Vialaphos, Vialaphos-sodium, Bipirazone, Bispi Rivac, Bispiribac-Sodium, Bixlozone, Bromacil, Bromacil-Lithium, Bromacil-Sodium, Bromobutide, Bromophenoxime, Bromoxynil, Bromoxynil-Butyrate, -Potassium, -Heptanoate and -Octanoate, Busoxynone, Butachlor, Butaphenacil, Butamiphos, Butenacrol, Buttraline, Butroxidime, Butyrate, Cafenstrol, Cambenichlor, Carbetamide, Carfent Lazon, Carfentrazon-ethyl, Chloramben, Chloramben-ammonium, Chloramben-diolamine, Chloramben-methyl, Chloramben-methylammonium, Chloramben-sodium, Chlorbromulone, Chlorfenac, Chlorfenac-ammonium, Chlorfenac-sodium, Chlorfenprop, Chlorfenprop-methyl, Chlorflurenol, Chlorflurenol-methyl, Chlorida Szon, Chlorimulone, Chlorimulone-ethyl, Chlophthalim, Chlortolurone, Chlorsulfuron, Chlortal, Chlortal-dimethyl, Chlortal-monomethyl, Synidone, Synidone-ethyl, Symmethiline, Exo-(+)-Symmethiline, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, Exo-(-)-Symmethiline, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, cinosulfuron, clasiphos, cretodym, clodinafop, clodinafop-ethyl, clodinafop-propargyl, chromazon, clomeprop, clopyralid, clopyralid-methyl, clopyralid-olamine, clopyralid-potassium, clopyralid-tripomine, chloranslam, chloranslam-methyl, cumylon, cyanamide, cyanazine, cycloate, cyclopyranil, Cyclopyrimolate, cyclosulfamurone, cycloxidium, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D(isoammonium, butotyl, butyl, choline, diethylammonium, dimethylammonium, diolamine, doboxyl, dodecylammonium, etexyl, ethyl, 2-ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, meptyl, methyl, potassium, tetradecylammonium, triethylammonium (including triisopropanolammonium, tripromine and trolamine salts), 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron, darapon, darapon-calcium, darapon-magnesium, darapon-sodium, dazomet, dazomet-sodium, n-decanol, 7-deoxy-D-sedoheptulose, desmedifam, detosylpyrazolate (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-diethanolamineammonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolamine, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine, diclobenyl, 2-(2,4-Dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidine-3-one, 2-(2,5-Dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidine-3-one, Dichloroprop, Dichloroprop-Butotyl, Dichloroprop-dimethylammonium, Dichloroprop-Etexyl, Dichloroprop-Ethylammonium, Dichloroprop-Isoctyl, Dichloroprop-Methyl, Dichloroprop-Potassium, Dichloroprop-Sodium, Dichloroprop Rop-P, Dichlorprop-P-dimethylammonium, Dichlorprop-P-ethexyl, Dichlorprop-P-potassium, Dichlorprop-sodium, Diclohop, Diclohop-methyl, Diclohop-P, Diclohop-P-methyl, Diclothram, Diphenzocoat, Diphenzocoat-methylsulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr-sodium, Dimeflon, Dimepiperate, Dimesulfazet, Dimethachlor, Dimethametrin, Dimethenamide, Dimethenamide-P, Dime Dimetrasulfuron, dinitramine, dinoterb, dinoterb acetate, diphenamide, diquat, diquat-dibromide, diquat-dichloride, dithiopyr, diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, endotar, endotar-diammonium, endotar-dipotassium, endotar-disodium, epiriphenacil (S-3100), EPTC, esprocarb, ethalfluralin, etametulfuron, etametulfuron-meth Lu, Ethiodin, Etofmesate, Ethoxyphen, Ethoxyphen-ethyl, Ethoxysulfuron, Etobenzanide, F-5231, i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazole-1-yl]-phenyl]ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazole-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, phenoxaprop, phenoxaprop-P, phenoxaprop-ethyl, phenoxaprop-P-ethyl, phenoxasulfone, fenpyrazone, fenquinotrione, phentrazamide, flamprop, flamprop-isoproyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, floraslam, florpyrauxifenbenzyl, florpyrauxifenbenzyl-benzyl, f Luadifop, fluadifop-butyl, fluadifop-methyl, fluadifop-P, fluadifop-P-butyl, flucarbazone, flucarbazone sodium, flucetosulfuron, fluchloralin, fluphenacet, flufenpyr, flufenpyr-ethyl, flumetulam, flumicrolac, flumicrolac-pentyl, flumioxazine, fluomethron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen N-ethyl, flupropanate, flupropanate-sodium, flupyrusulfuron, flupyrusulfuron-methyl, flupyrusulfuron-methyl-sodium, flulidone, fluorochloridone, fluroxypyr, fluroxypyr-butomethyl, fluroxypyr-meptyl, flulutamone, fluthiaset, fluthiaset-methyl, fomesaphen, fomesaphen-sodium, horamsulfuron, horamsulfuron sodium salt, hosamin, hosamin- Ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate (glufosiante)-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium, sesquisodium and -trimethium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioate, halaxifen, halaxifen-methyl, halosaphen, halosulfuron, halosulfuron-methyl, haloxyhop, haloxyhop-P, haloxyhop-ethoxyethyl, haloxyhop-P-ethoxyethyl, haloxyhop-methyl, haloxyhop-P-methyl, haloxyhop-sodium, hexazinone, HNPC-A8169, i.e., propa-2-in-1-yl(2S)-2-{3-[(5-tert-butylpyridine-2-yl)oxy]phenoxy}propanoate, HW-02, i.e., 1-(dimethoxyphosphoryl)-ethyl-(2,4-dichlorophenoxy)acetate, hydantosidine, imazametabenz, imazametabenz-methyl, imazametabenz Zamox, Imazamox-ammonium, Imazapick, Imazapick-ammonium, Imazapyr, Imazapyr-isopropylammonium, Imazakine, Imazakine-ammonium, Imazakine-methyl, Imazetapir, Imazetapir-immonium, Imazosulfuron, Indanophan, Indadiflame, Iodosulfuron, Iodosulfuron-methyl, Iodosulfuron-methyl-sodium, Ioxinyl, Ioxinyl-lithium, -octanoate, -potassium and sodium, Ipfencarbazone, Isoproturone, Isouron, Isoxaben, Isoxaflutol, Carbutyrate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-Oxazole, Ketospiradox, Ketospiradox-Potassium, Lactofen, Renacil, Linuron, MCPA, MCPA-Butotyl,-Butyl,-Dimethylammonium,-Diolamine,-2-Ethylhexyl,-Ethyl,-Isobutyl, Isoctyl,-Isopropyl,-Isopropylammonium,-Methyl, Olamine,-Potassium,-Sodium and-Trolamine, MCPB, MCPB-Methyl,-Ethyl and-Sodium, Mecoprop, Mecoprop-Butotyl, Mecoprop-Demethylammonium, Mecoprop-Diolamine, Me Mecoprop-etexyl, mecoprop-etadyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium, and mecoprop-trolamine, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mefluidide-diolamine, mefluidide potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron sodium salt, mesotrione, metabenzthiazuron, metam, metamihop, metamitron, Metazachlor, metazometazosulfuron, metabenzthiazulon, methiopyrsulfuron, methiozoline, methylisothiocyanate, metobromurone, metrachlor, S-metrachlor, metoslam, metoxuron, metrivudine, metosulfuron, metosulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-methyl, MT-5950, i.e., N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide, NGG C-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-oxadiazole-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, Nebulon, Nicosulfuron, Nonanoic acid (pelargonic acid), Norflurazone, Oleic acid (fatty acid), Olbencarb, Orthosulfamurone, Oryzalin, Oxadia Lugyl, oxadiazone, oxasulfuron, oxadiclomefone, oxyfluorophene, paraquat, paraquat-dichloride, paraquat-dimethylsulfate, pevlate, pendimethalin, penoxsullam, pentachlorophenol, pentoxazone, petoxamide, petroleum, fenmedifam, fenmedifam-ethyl, picloram, picloram-dimethylammonium, picloram-etexyl, picloram-isoctyl, picloram-methyl, picloram-olamine, picloram-potassium, picloram-to Liethylammonium, picloram-tripromine, picloram-trolamine, picolinafene, pinoxadene, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, prophoxidime, prometon, prometrin, propacrol, propanil, propaxafop, propazine, profam, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propizamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl,Pyrasulfolol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyrifthalide, pyriminovac, pyriminovac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxislam, quinchlorac, quinchlorac-dimethylammonium, quinchlorac-methyl, quinmelac, quinoclamin , quizalophop, quizalophop-ethyl, quizalophop-P, quizalophop-P-ethyl, quizalophop-P-tefuryl, QYM201, i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazole-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidine-2-one, limsulfuron, saflufenacil, cethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfenthrazone, sulfomethane, sulfomethane-methyl, sulfosulfuron, S YP-249, i.e., 1-ethoxy-3-methyl-1-oxobuta-3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(propa-2-in-1-yl)-3,4-dihydro-2H-1,4-benzoxazine-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, e.g., TCA-ammonium, TCA-calcium, TCA- Ethyl, TCA-magnesium, TCA-sodium, tebuthiurone, tefuryltrione, tenbotrione, tepraloxidim, terbasil, terbucarb, terbumetone, terbutyrazine, terbutrin, tetoflupyrrolimet, saxtomin, tenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiafenasil, tolpyrate, topramezone, tralcoxidim, triafamone, triate, triasulfuron, triaziflame, tribenulon,Trivenuron-methyl, Triclopyr, Triclopyr-butotyl, Triclopyr-choline, Triclopyr-ethyl, Triclopyr-triethylammonium, Trietadine, Trifloxysulfuron, Trifloxysulfuron-sodium, Trifludimoxazine, Trifluralin, Triflusulfuron, Triflusulfuron-methyl, Tritosulfuron, Urea sulfate, Vernolate, XDE-848, ZJ-0862, i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidine-2-yl)oxy]benzyl}aniline, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidine-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate ethyl ester, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl-5-chloropyrimidine-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohexa-1-en-1-yl)carbonyl]-6-methylpyridazine-3( 2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridine-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazole-4-yl)(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazole-5-ylpropane-1-sulfonate, 4- {2-chloro-3-[(3,5-dimethyl-1H-pyrazole-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazole-5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate; cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, propa-2-in-1-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate,Methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, ethyl 4-amino-3-chloro-5-fluoro-6-(7- Luoro-1H-indole-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indole-6-yl)pyridine-2-carboxylate, methyl 6-(1-acetyl-7-fluoro-1H-indole-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl) -7-Fluoro-1H-indole-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indole-6-yl]pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, sodium 4-amino-3-chloro-5-fluoro-6- (7-Fluoro-1H-Indole-6-yl)pyridine-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-Fluoro-1H-Indole-6-yl)pyridine-2-carboxylate, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridine-2-yl]imidazolidined-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidined-2-one, Abscisic acid, acibenzol, acibenzol-S-methyl, 1-aminocyclopropane-1-ylcarboxylic acid and its derivatives, 5-aminolevulinic acid (Aminolavulinsaure), ancimidol, 6-benzylaminopurine, brassinolide, brassinolide-ethyl, catechin, chito-oligosaccharide (CO; CO differs from LCO in that it does not have the pendant fatty acid chain that is characteristic of LCO. CO is sometimes called N-acetyl chito-oligosaccharide and is similarly composed of GlcNAc residues, but the chitin molecule [(C8-H 13 NO5) n , CAS number 1398-61-4] and chitosan molecule [(C5H 11 NO4) n[CAS No. 9012-76-4] (having a different side chain decoration), chitinous compounds, chlormecoat chloride, croprop, cyclanilide, 3-(cyclopropa-1-enyl)propionic acid, daminozide, dazomet, dazomet-sodium, n-decanol, dikeglac, dikeglac-sodium, endotal, endotal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), etephon, flumetraline, flurenol, flurenol-butyl, flurenol-methyl Chill, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyrate, isoprothiolane, probenazole, jasmonic acid, jasmonic acid or its derivatives (e.g., methyl jasmonate), lipo-chitooligosaccharide (LCO), sometimes called symbiotic nodule (Nod) signaling (or Nod factor), or Myc factor, and β-1,4-linked N-acetyl-D-glucosamine ("Gl"), in which N-linked fatty acid acyl chains are condensed at the non-reducing end. It consists of an oligosaccharide skeleton of cNAc residues. As understood in the art, LCOs differ in the number of GlcNAc residues in the skeleton, the length and saturation of the fatty acid acyl chain, and the substitution of reducing and non-reducing sugar residues. Other LCOs include linoleic acid or its derivatives, linolenic acid or its derivatives, maleic acid hydrazide, mepicote chloride, mepicote pentaborate, 1-methylcyclopropene, 3'-methylabscisic acid, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, and nitrophenolate mixtures. 4-Oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid, N-phenylphthalamiic acid, prohexadione, prohexadione-calcium, prohydrojasmon, salicylic acid, methyl salicylate, strigolactone, technazene, tidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine.

[0034] The active compound or combination / composition of the active compound can be converted into commonly used formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension emulsion concentrates, natural and synthetic formulations, natural and synthetic materials impregnated with the active compound, and very fine capsules in polymeric materials.

[0035] These formulations are produced by known methods, for example, by mixing an active compound with an expander, i.e., a liquid solvent and / or a solid carrier, and optionally with a surfactant, i.e., an emulsifier and / or a dispersant and / or a foaming agent.

[0036] If the bulking agent used is water, it is also possible to use, for example, an organic solvent as an auxiliary solvent. Suitable liquid solvents are basically aromatics, such as xylene, toluene, or alkylnaphthalenes; chlorinated aromatic and chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene, or methylene chloride; aliphatic hydrocarbons, such as cyclohexane or paraffin; petroleum fractions, mineral oils, and vegetable fats; alcohols, such as butanol or glycols, as well as their ethers and esters; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide; and also water.

[0037] A suitable solid carrier is, Suitable solid carriers for the granules include, for example, ammonium salts and crushed natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, or diatomaceous earth, and crushed synthetic minerals such as fine silica, alumina, and silicates; suitable solid carriers for the granules include, for example, crushed and fragmented natural rocks such as calcite, marble, pumice, meerschmitt, and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic materials such as sawdust, coconut shells, corn cobs, and tobacco stalks; suitable emulsifiers and / or foaming agents include, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylallyl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, and protein decomposition products; suitable dispersants include, for example, lignosulfite wastewater and methylcellulose.

[0038] Tackifiers, such as carboxymethylcellulose in the form of powder, granules, or latex, and natural and synthetic polymers, such as gum arabic, polyvinyl alcohol, and polyvinyl acetate, as well as natural phospholipids such as cephalin and lecithin, and synthetic phospholipids, can be used in the formulation. Other possible additives include mineral oil and vegetable oil.

[0039] Inorganic pigments, such as iron oxide, titanium dioxide, and Prussian blue, as well as organic dyes, such as alizarin dyes, azo dyes, and metal phthalocyanine dyes, and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc, can be used.

[0040] The formulation generally contains 0.1 to 95% by weight, preferably 0.5 to 90%, of active compounds, including drug-induced harm reduction agents.

[0041] The combination of active compounds according to the present invention is generally used in the form of a final formulation. However, the active compounds included in the combination of active compounds can also be mixed into individual formulations at the time of use, i.e., in the form of a tank mix.

[0042] Novel combinations of active compounds can be used as is, in their formulations, or in mixtures with other known herbicides, whether in the final formulation or tank mix. Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, growth factors, plant nutrients, and soil structure improving agents, are also possible. Particularly for specific uses in post-emergence methods, it may be even more advantageous to include plant-tolerant mineral or vegetable oils (e.g., the commercially available preparation "Rako Binol") or ammonium salts such as ammonium sulfate or ammonium thiocyanate as further additives in the formulation.

[0043] Novel combinations of active compounds can be used as is, in their formulation form, or in forms of use prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes, and granules. They can be used in conventional methods, such as washing, spraying, atomizing, dusting, or dispensing.

[0044] The advantageous effect of the crop-plant compatibility of the combination / composition of active compounds according to the present invention is particularly highly pronounced in certain amounts of herbicides and phytotoxicity reducers.

[0045] The application rates of the combination of active compounds according to the present invention may vary within a certain range; they are particularly dependent on weather and soil factors.

[0046] Generally, for example, in tank mix application, the application rate of herbicides is 0.1 to 1000 g / ha, preferably 1 to 50 g / ha. The application rate of phytotoxicity reducers is 1 to 1000 g / ha, preferably 10 to 200 g / ha.

[0047] For seed treatment applications, the herbicide application rate is between 0.1 and 1000 g / ha, preferably between 10 and 100 g / ha, and most preferably between 30 and 100 g / ha. The phytotoxicity reduction agent application rate is between 0.01 and 2 g per kg of seed, preferably between 0.1 and 1 g per kg of seed.

[0048] The combination of active compounds according to the present invention can be applied before and after plant emergence, that is, by methods used both before and after emergence.

[0049] Examples of use: Tank mix; after germination A) Explanation of the method Seeds of crops (spring wheat, TRZAS; spring barley, HORVS; maize, ZEAMA) were placed in sandy loam in peat pots, covered with soil, and cultivated in a greenhouse under favorable growing conditions. Two to three weeks after sowing, test plants were treated at the 1-leaf to 3-leaf stage. Combinations of active compounds of the herbicide / phytotoxicity reducer according to the present invention, formulated as wettable powders or emulsion concentrates, and the correspondingly formulated individual active compounds, were sprayed at various doses onto the green parts of the plants using a water volume of 300 l / ha (equivalent) in parallel tests.

[0050] The pots were returned to the greenhouse under favorable growing conditions, and the herbicidal effect was visually evaluated at intervals of 1 to 3 weeks (DAT = days after treatment) following herbicide application. The evaluation was based on a percentage compared to untreated control plants (0% = undamaged, 100% = completely dead).

[0051] The effectiveness of the drug damage reduction agent treatment is shown as follows: Mitigation [Difference] = Damage from herbicide without phytotoxicity reducer - Damage from herbicide with phytotoxicity reducer Reduction rate [%] = (Reduction [difference] * 100) / Damage from herbicide without phytotoxicity reducer B) Table containing data Plant species and variety: ZEAMA Sileno, phytotoxicity reduction agent (SAF): Flirazole

[0052] [Table 2]

[0053] Seed treatment; before germination A) Explanation of the method For seed treatment with phytotoxicity-reducing agents, a sufficient amount of seeds for each crop (spring wheat, TRZAS; spring barley, HORVS; corn, ZEAMA) was weighed into screw-top glass bottles approximately twice the volume of the seeds.

[0054] A designated phytotoxicity-reducing agent, formulated as a wettable powder (WP), was weighed out to obtain the specified ratio (g ai / kg seed), dissolved in water (1 ml of water per 10 g of seed), and added to the seeds to prepare a slurry.

[0055] After capping the jars, the seeds were placed in an overhead shaker (set to medium speed for approximately 60 minutes) to ensure they were evenly coated with the slurry. The jars were then uncapped, and the seeds were placed on paper to dry for 3-4 hours before sowing, or they were sown directly. The seeds were placed in sandy loam in pots 7-8 cm in diameter and covered with soil.

[0056] Subsequently, the specified herbicide was applied to two sets of plants after germination. a) Seed treatment with the above-mentioned phytotoxicity-reducing agent b) No treatment with phytotoxicity reduction agent

[0057] The herbicide was formulated as WP and sprayed onto the soil surface as an aqueous suspension at a water application rate equivalent to 300 l / ha.

[0058] After application, the test plants were kept under favorable growing conditions in a greenhouse. At intervals of up to 4 weeks (28 days post-treatment; DAT) after application, the crop damage rate observed in the treated plants was visually scored compared to control plants that had not received phytotoxicity reducer or herbicide treatment.

[0059] The values ​​in the table below are the mean values ​​over at least two replicates.

[0060] The effectiveness of the drug damage reduction agent treatment is shown as follows: Mitigation [Difference] = Damage from herbicide without phytotoxicity reducer - Damage from herbicide with phytotoxicity reducer Reduction rate [%] = (Reduction [difference] * 100) / Damage from herbicide without phytotoxicity reducer B) Table containing data Plant species and variety: ZEAMA Sileno, phytotoxicity reduction agent (SAF): Flirazole

[0061] [Table 3]

Claims

1. (a) Substituted isoxazoline carboxamide of formula (I) or a pesticide-acceptable salt thereof 【Chemistry 1】 (In the formula, G is OR 4 or NR 7 R 8 Represents R 1 and R 2 Each represents hydrogen; R 3 is substituted "m" times with substituents selected from the group consisting of halogen, cyano, (C 1 to C 5 )-alkoxy and hydroxy, and represents (C 1 to C 5 )-alkyl, (C 3 to C 6 )-cycloalkyl, (C 2 to C 5 )-alkenyl, (C 2 to C 5 )-alkynyl or (C 1 to C 5 )-alkoxy; R 4 Does this represent hydrogen? or Depending on the case, halogen, cyanoacrylate, (C 1 ~C 6 )-alkoxy, (C 1 ~C 6 )-alkoxycarbonyl, hydroxy, S(O) n R 5 (C 1 ~C 12 )-alkyl, (C 3 ~C 7 )-cycloalkyl, (C 3 ~C 7 )-cycloalkyl-(C 1 ~C 8 )-alkyl, (C 2 ~C 8 ) - Alkenil, (C 5 ~C 6 )-cycloalkenyl, (C 1 ~C 4 )-alkylphenyl or (C 2 ~C 8 ) - Represents Alkinnil; R 5 Each is substituted "m" times with substituents from the group consisting of halogens and cyanos, (C 1 ~C 8 )-alkyl, (C 2 ~C 8 ) - Alkenil, (C 3 ~C 6 )-Cycloalkyl, benzyl, CON((C 1 ~C 3 )-alkyl) 2 or (C 1 ~C 8 )-alkyl-C(O)-(C 1 ~C 8 ) - Represents alkyl; R 6 Does this represent hydrogen? or Depending on the case, halogen, cyano and (C) 1 ~C 2 (C) is substituted "m" times with substituents from the group consisting of alkoxys. 1 ~C 8 )-alkyl, (C 3 ~C 6 )-cycloalkyl, (C 3 ~C 8 )-Alkenyl or (C 3 ~C 8 ) - Represents Alkinnil; R 7 , R 8 They are independent of each other, hydrogen, (C 1 ~C 6 )-alkoxycarbonyl-(C 1 ~C 6 )-alkyl, N((C 1 -C 3 )-alkyl) 2 , S(O) n R 5 Does it represent, or R 7 and R 8 It may also contain, separately from the nitrogen atoms (atom) to which they are bonded, "r" carbon atoms and "o" oxygen atoms, and optionally halogens, (C 1 ~C 6 )-alkyl, halogen-(C 1 ~C 6 )-alkyl, oxo, CO 2 R 6 Forming a saturated, partially unsaturated, or fully unsaturated 5, 6, or 7-membered ring that is "m" substituted with substituents from the group consisting of; Z is Z-1 to Z-8: 【Chemistry 2】 This represents the bonding of formula (I) to the group CO-G, and the arrow indicates the bonding of the group CO-G to the group CO-G; X 2 , X 4 and X 6 These represent hydrogen or fluorine independently of each other; X 3 and X 5 each independently represents hydrogen, chlorine, cyano or fluorine; or Each case is substituted m times with substituents from the group consisting of fluorine or chlorine (C 1 ~C 3 )-alkyl, (C 1 ~C 3 ) - Represents alkoxy; 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) Frillazole A combination that includes this.

2. The combination according to claim 1, characterized in that the compound of formula (I) is (Ia) or a pesticide-permissible salt thereof. 【Transformation 3】 (In the formula, X 3 、 X 5 、 R 3 and G are as described above; Z is Z-1a, Z-1b, Z-2a, Z-3a, Z-4a, Z-5a, Z-6a, Z-7a, Z-8a 【Chemistry 4】 Meaning, Z-4a is a mixture of structures Z-4b and Z-4c. 【Transformation 5】 It means; Z-8a is a mixture of structures Z-8b and Z-8c. 【Transformation 6】 It means; The aforementioned arrows indicate the bond to the group CO–G in formula (Ia).

3. The combination according to claim 1 or 2, wherein the application rate of the herbicide is between 0.1 and 1000 g / ha, preferably between 1 and 50 g / ha, and the application rate of the phytotoxicity reducer is between 1 and 1000 g / ha, preferably between 10 and 200 g / ha.

4. Use of any one of the combinations described in claims 1 to 3 for controlling undesirable plants.

5. A method for controlling undesirable plants, characterized by applying the combination described in any one of claims 1 to 3 to the undesirable plants and / or their habitat.

6. A composition comprising a surfactant and / or a bulking agent in addition to the combination described in any one of claims 1 to 3.

7. A method for preparing the herbicide composition according to claim 6, characterized in that the combination according to any one of claims 1 to 3 is mixed with a surfactant and / or a bulking agent.

8. A method for reducing crop damage, characterized by treating the seeds of the crop with flirazole before sowing (Step 1), and applying a compound of formula (I) or a combination / composition containing the same as described in any one of claims 1 to 3 and 6 as a post-emergence treatment (Step 2).

9. A method for reducing crop damage, characterized by treating the seeds of the crop with flirazole before sowing (Step 1), and applying a compound of formula (I) or a combination / composition containing the same as described in any one of claims 1 to 3 and 6 as a pre-emergence treatment (Step 2).

10. The method according to any one of claims 5, 8, or 9, wherein the crop is a genetically modified plant.

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