Sulfoximinobenzamides having herbicidal action

Abstract

This invention relates to sulfonylimide benzamide of formula (I) as a herbicide. In formula (I), X, W, Z, R, R', and R'' represent groups such as alkyl, cycloalkyl, haloalkyl, and halogen groups.

Description

[0001] This invention relates to the technical field of herbicides, and in particular to herbicides for the selective control of broadleaf weeds and grass weeds in plant crops.

[0002] WO 2011 / 035874 A1 discloses N-(1,2,5-oxadiazol-3-yl)benzamides with herbicidal activity. European patent application EP10174893, whose priority date predates that of this invention but was not published prior to the priority date of this application, discloses specific N-(tetrazole-5-yl)- and N-(triazol-5-yl)benzamides and N-(tetrazole-5-yl)- and N-(triazol-5-yl)nicotinamides as herbicides. WO 2013 / 124228 discloses 3-sulfinyliminobenzamides and 3-sulfinyliminobenzamides with herbicidal activity. However, the herbicidal activity and / or crop compatibility of the compounds described in these publications are not always satisfactory.

[0003] The object of this invention is to provide a herbicidal active compound that has improved properties compared with compounds disclosed in the prior art.

[0004] It has been found that certain sulfonyliminobenzamides with an unsubstituted 1,3,4-oxadiazole atom on the amide nitrogen atom are particularly suitable as herbicides. Therefore, the present invention provides sulfonyliminobenzamides of formula (I) or salts thereof. The symbols are defined as follows: X is a halogen, cyano, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkylthio, halogen-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, or (C3-C6)-cycloalkyl. Z represents halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-ynyl, halo-(C3-C6)-ynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, halo-(C1-C6)-alkoxy, (C1-C6)-alkylsulfonyl. W represents hydrogen or halogen. R is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, or (C1-C6)-alkoxy-(C1-C6)-alkyl. R' is hydrogen, cyano, or (C1-C6)-alkyl. R'' represents hydrogen or (C1-C6)-alkyl carbonyl.

[0005] In formula (I) and all the following formulas, the alkyl group having two or more carbon atoms can be straight-chain or branched. The alkyl group is, for example, methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, tert-butyl or 2-butyl, pentyl, and hexyl (e.g., n-hexyl, isohexyl, and 1,3-dimethylbutyl). Similarly, the alkenyl group is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. The alkynyl group is, for example, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be located at any position in each unsaturated group. Cycloalkyl refers to a carbon-cyclic saturated ring system having three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0006] "Haloalkyl," "haloalkenyl," and "haloalkynyl" refer to alkyl, alkenyl, and alkynyl groups that are partially or completely substituted with the same or different halogen atoms, respectively. Examples include monohaloalkyl groups such as CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, and CH2F; dihaloalkyl groups such as CH2CHF2, CH2CHCl2, CH2CHBr2, CF2CH3, CHCl2, and CHF2; perhaloalkyl groups such as CCl3, CFCl2, CClF2, CF3, CF2CClF2, and CF2CClFCF3; and polyhaloalkyl groups such as CH2CHFCl, CF2CClFH, CF2CBrFH, and CH2CF3. The term perhaloalkyl also includes the term perfluoroalkyl.

[0007] "Alkoxy" refers to an alkyl group linked by an oxygen atom, such as (but not limited to) (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, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, etc. 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.

[0008] "Alkoxyalkyl" refers to an alkoxy group linked by an alkyl group.

[0009] "Haloalkoxy" refers to a haloalkyl group linked by an oxygen atom, such as (but not limited to) OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl.

[0010] According to the present invention, "alkylthio" refers to a straight-chain or branched S-alkyl group, such as (C1-C6)-alkylthio, for example, methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1 -Methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutyrothio, 1,2-dimethylbutyrothio, 1,3-dimethylbutyrothio, 2,2-dimethylbutyrothio, 2,3-dimethylbutyrothio, 3,3-dimethylbutyrothio, 1-ethylbutyrothio, 2-ethylbutyrothio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

[0011] According to the present invention, unless otherwise defined, "alkyl carbonyl" (alkyl-C(=O)-) refers to an alkyl group attached to the backbone by -C(=O)-, such as (C1-C6)-alkyl carbonyl. The number of carbon atoms here refers to the alkyl group in the alkyl carbonyl group.

[0012] The term "halogen" refers to, for example, fluorine, chlorine, bromine, or iodine. If the term is used with a group, "halogen" refers to, for example, a fluorine, chlorine, bromine, or iodine atom.

[0013] If a compound can form tautomers via hydrogen migration, and these tautomers are not structurally included in formula (I), then these tautomers are still included within the definition of compounds of formula (I) of this invention, unless a specific tautomer is being considered. For example, many carbonyl compounds may exist simultaneously in both keto and enol forms, both of which are included within the definition of compounds of formula (I).

[0014] Depending on the nature of the substituents and their linkage, compounds of general formula (I) may exist as stereoisomers. For example, enantiomers and diastereomers may occur if one or more asymmetrically substituted carbon atoms are present. Furthermore, the sulfur atom in the sulfoxide imine group serves as a chiral center. Stereoisomers can be obtained from mixtures obtained during the preparation process using conventional separation methods (e.g., chromatographic separation). Similarly, stereoisomers can be selectively prepared by using stereoselective reactions of optically active starting materials and / or auxiliaries. This invention also relates to all stereoisomers of general formula (I) but not specifically defined, and mixtures thereof. This invention also relates to all E / Z isomers of general formula (I) but not specifically defined, and mixtures thereof.

[0015] Compounds of formula (I) can form salts. Salts can be formed by reacting a base with a compound of formula (I) containing an acidic hydrogen atom, for example, in the case of R''. Examples of suitable bases are organic amines, such as trialkylamines, morpholine, piperidine, or pyridine, as well as ammonium, alkali metal or alkaline earth metal hydroxides, carbonates, and bicarbonates, especially sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, such as metal salts, especially alkali metal or alkaline earth metal salts, particularly sodium and potassium salts, or ammonium salts, with salts of organic amines or quaternary ammonium salts, for example having the formula [NRR*R**R***]. + A cation salt, wherein R, R*, R**, and R*** each independently represent an organic group, particularly alkyl, aryl, aralkyl, or alkylaryl. Also useful are alkylsulfonium salts and alkyloxonium salts, such as (C1-C4)-trialkylsulfonium salts and (C1-C4)-trialkyloxonium salts.

[0016] Compounds of formula (I) can form salts by addition of a suitable inorganic or organic acid to a basic group, such as mineral acids (e.g., HCl, HBr, H₂SO₄, H₃PO₄, or HNO₃) or organic acids (e.g., carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or sulfonic acids, such as p-toluenesulfonic acid), and the basic group, such as amino, alkylamino, dialkylamino, piperidinyl, morpholinyl, or pyridinyl. These salts contain the conjugate base of the acid as an anion.

[0017] Compounds of preferred general formula (I), wherein X is a halogen, (C1-C3)-alkyl, (C1-C3)-alkoxy, or (C3-C6)-cycloalkyl. Z represents halogen, (C1-C3)-alkyl, halogen-(C1-C3)-alkyl, (C1-C3)-cycloalkyl, or halogen-(C1-C3)-alkoxy. W represents hydrogen or fluorine. R is (C1-C3)-alkyl. R' is hydrogen. R'' represents hydrogen.

[0018] Compounds of general formula (I) are particularly preferred, wherein X can be chloro, methyl, ethyl, methoxy, or cyclopropyl. Z represents chloro, methyl, difluoromethyl, trifluoromethyl, cyclopropyl, or trifluoromethoxy. W represents hydrogen. R represents methyl or ethyl. R' is hydrogen. R'' represents hydrogen.

[0019] The compounds of the present invention can be prepared according to the method described in WO 2013 / 124228.

[0020] Therefore, the compounds of the present invention can be prepared stepwise, for example, according to the method shown in Scheme 1, firstly by reacting benzoyl chloride (II) with 2-amino-1,3,4-oxadiazole (VII) in the thioether stage of formula (I-thioether). Then, according to Scheme 4, the thioether intermediate is converted into the sulfonylimide benzamide of formula (I) of the present invention. The compounds of the present invention can also be prepared stepwise according to the method shown in Scheme 2, firstly by reacting benzoic acid of formula (IV) with 2-amino-1,3,4-oxadiazole (VII) in the thioether stage of formula (I-thioether). Then, according to Scheme 4, the thioether intermediate is converted into sulfonylimide benzamide of formula (I) of the present invention. For activation, dehydrating agents commonly used in amidation reactions can be used, such as 1,1'-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphonaxane-2,4,6-trioxide (T3P).

[0021] The compounds of the present invention in which the substituent R'' is not hydrogen can be prepared, for example, according to the method shown in Scheme 3, by reacting N-(1,3,4-oxadiazol-2-yl)-arylformamide (I-NH) with a compound of general formula (VIII), wherein L is a leaving group, such as chlorine, bromine, iodine, methanesulfonyloxy, p-toluenesulfonyloxy, trifluorosulfonyloxy, etc. The compounds of formula (VIII) are commercially available or can be prepared by known methods described in the literature.

[0022] The compounds of formula (I) of the present invention can be prepared, for example, from thioethers of the corresponding formula (I-thioether) (Scheme 4). For this purpose, the thioether is converted, for example, by cyanamide and an oxidizing agent (iodophenylacetate, sodium hypochlorite, or N-bromosuccinimide) to the corresponding sulfilimine, which can be further oxidized to sulfoximine. Examples of suitable oxidizing agents for oxidation to sulfoximine are m-chloroperoxybenzoic acid, sodium permanganate, or a mixture of sodium periodate and ruthenium trichloride. NH-sulfoximine can be obtained, for example, by sulfoxide with sodium azide and sulfuric acid, and can be functionalized at the nitrogen atom with a reagent such as cyanogen bromide, acyl chloride or acid anhydride, chloroformate, nitric acid, or other compounds. N-sulfonated sulfilimine can be oxidized to the corresponding sulfoximine, for example by oxidation with hydrogen peroxide. Alternatively, sulfoxide can react to generate N-acylated or N-sulfonated sulfoximine. Formamide or sulfonamide can then be decomposed to NH-sulfoximine. Methods for synthesizing thioimines and sulfoxides from thioethers, methods for synthesizing sulfoxides from sulfoxides, or methods for synthesizing thioimines and sulfoxides (including NH-sulfoxides) by decomposition are described, for example, in Bolm, C. Org. Lett. 2004, 6, 1305; Bolm, C. Org. Lett. 2007, 9, 3809; Bolm, C. Synthesis 2010, 17, 2922; Bolm, C. Adv. Synth. Catal. 2010, 352, 309; WO 2007 / 095229, WO 2008 / 141843, US 2008 / 0207910, US 2008 / 0194634, and US2010 / 0056534. When necessary, such synthetic routes require the use of protecting groups to obtain sufficient selectivity. In particular, functionalization on NH-sulfonyl imines is, in principle, in competition with similar functionalization on the amide nitrogen atom.

[0023] Changing the order of reaction steps may be more convenient. For example, benzoic acid with a sulfoxide group is not readily converted to its acyl chloride. One approach is to prepare the amide first in the thioether stage and then oxidize the thioether to sulfoxide. Sulfoxide imides, especially thioimides, are not sufficiently stable under certain conditions (Bolm, C. Adv. Synth. Catal. 2010, 352, 309). Therefore, as shown in the above scheme, it may be more advantageous to synthesize benzamide first in the thioether stage and then generate thioimide or sulfoxide imide from the thioether in the final stage of the synthesis sequence. However, if the stability is good enough, depending on the substitution pattern, it is also possible to generate thioimide or sulfoxide imide from the thioether first in the benzoic acid stage (or an earlier step) and then convert benzoic acid to its amide.

[0024] Using derivatives of benzoic acid may be more advantageous than using free benzoic acid in the reaction. Sometimes, the functional group is stable enough to allow it to move only in acidic or basic media; that is, only free benzoic acid or its salts may be used. In many cases, esters (e.g., methyl or ethyl esters) are suitable. Tert-butyl esters generally effectively protect the carboxyl group from nucleophiles and are readily decomposed in acidic media (TW Greene, PGM Wuts, Protective Groups in Organic Synthesis, 2nd ed., John Wiley & Sons, Inc. 1991, p. 227 and subsequent pages). Furthermore, some groups that are more stable than the carboxyl group but readily available from carboxylic acids and easily converted back to free carboxylic acids are also suitable. These include, for example, oxazoline (TW Greene, PGM Wuts, Protective Groups in Organic Synthesis, 2nd ed., John Wiley & Sons, Inc. 1991, p. 265 and following pages; Z. Hell et al., Tetrahedron Letters 43 (2002), 3985-3987).

[0025] Alternatively, the NH-sulfonyl imine of formula (I) of the present invention can be obtained in one step from the corresponding sulfide of formula (I-sulfide) (Scheme 5). For this purpose, the sulfide can be directly converted into the corresponding NH-sulfonyl imine, for example with ammonium carbamate and iodophenyl diacetate (JA Bull et al. Synlett 2017, 28, 2525-2538). In the above synthetic method, the sulfoxide imine of formula (I) of the present invention is obtained in the form of a racemic mixture other than the sulfoxide imine. Pure enantiomers can be obtained by chiral separation methods known to those skilled in the art, for example by chromatographic separation of enantiomers on a chiral support material.

[0026] The treatment of the corresponding reaction mixture is usually accomplished by known methods, such as crystallization, aqueous extraction, chromatography, or a combination of these methods.

[0027] The collection of compounds of formula (I) and their salts, synthesized by the above reactions, can also be prepared in parallel, and the process can be carried out manually, semi-automatically, or fully automatically. For example, the reaction, post-processing, or purification of products and / or intermediates can be automated. In summary, this should be understood to refer, for example, to the methods described by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (edited by Günther Jung) Wiley, 1999, pp. 1-34.

[0028] To enable parallel operation of the reaction and post-processing, a range of commercially available equipment can be used, such as the Calypso reaction module from Barnstead International, Dubuque, Iowa 52004-0797, USA; reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB11 3AZ, England; or the MultiPROBE automated workstation from Perkin Elmer, Waltham, Massachusetts 02451, USA. For parallel purification of compounds of formula (I) and their salts, or intermediates generated during preparation, a chromatograph can be used, such as one from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

[0029] The listed equipment constitutes a modular process in which each work step is automated, but manual intervention is still required between steps. This can be avoided by using partially or fully integrated automation systems, in which the corresponding automation modules can be operated by, for example, robots. Such automation systems are available, for example, from Caliper, Hopkinton, MA 01748, USA.

[0030] Polymer-loaded reagent / scavenger resins can be used to assist in the operation of one or more synthetic steps. For example, a series of experimental protocols are described in the professional literature of ChemFiles, Volume 4, Issue 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

[0031] In addition to the methods described herein, compounds of general formula (I) and their salts can also be prepared, wholly or partially, by solid-phase loading. For this purpose, each or all intermediates involved in the synthesis, or applicable to the corresponding step, are combined with a synthetic resin. Solid-phase loading synthesis is well documented in the technical literature, for example, in Barry A. Bunin's "The Combinatorial Index," Academic Press, 1998, and Combinatorial Chemistry - Synthesis, Analysis, Screening (edited by Günther Jung), Wiley, 1999. The use of solid-phase loading synthesis enables the implementation of many known schemes, which can be performed manually or automatically. For example, the IRORI technique can be used in a microreactor purchased from Nexus Biosystems, 12140 Community Road, Poway, CA 92064, USA.

[0032] Microwave technology can assist in completing one or more synthetic steps, whether in the solid or liquid phase. Many experimental protocols have been documented in professional literature, such as in Microwaves in Organic and Medicinal Chemistry (edited by CO Kappe and A. Stadler), Wiley, 2005.

[0033] The method described herein yields compounds of formula (I) and their salts existing as a collection of substances, referred to as a library. This invention also provides a library comprising at least two compounds of formula (I) and their salts.

[0034] The compounds of formula (I) of this invention (and / or their salts), hereinafter collectively referred to as "the compounds of this invention," exhibit excellent weed control effects against a variety of monocot and dicot annual pests of significant economic value. The active ingredients also demonstrate good control effects against perennial pests that are difficult to control and can sprout new shoots from rhizomes, rootstocks, or other perennial organs.

[0035] Therefore, the present invention also provides a method for controlling harmful plants or regulating plant growth, preferably in plant crops, wherein one or more compounds of the present invention are applied to the plant (e.g., harmful plants, such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), seeds (e.g., cereals, seeds, or vegetative propagules, such as tubers or budded stem segments), or the area where the plant grows (e.g., cultivated area). The compounds of the present invention can be applied, for example, before sowing (and, if appropriate, mixed into the soil), before emergence, or after emergence. Examples of some representative monocotyledonous and dicotyledonous weed groups that can be controlled by the compounds of the present invention are given below, and the following list is not limited to specific species.

[0036] The following genera are considered harmful monocotyledonous plants: *Aegilops*, *Agropyron*, *Agrostis*, *Alopecurus*, *Apera*, *Avena*, *Brachiaria*, *Bromus*, *Cenchrus*, *Commelina*, *Cynodon*, *Cyperus*, *Dactyloctenium*, *Digitaria*, *Echinochloa*, *Eleocharis*, *Eleusine*, and *Eragrostis*. Genuses: Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochooria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0037] The following genera of dicotyledonous weeds are: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, and Cirsiu. m), Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia The genera *Matricaria*, *Mentha*, *Mercurialis*, *Mullugo*, *Myosotis*, *Papaver*, *Pharbitis*, *Plantago*, *Polygonum*, *Portulaca*, *Ranunculus*, *Raphanus*, *Rorippa*, *Rotala*, *Rumex*, and *Salsola* are mentioned. The genera *alsola*, *Senecio*, *Sesbania*, *Sida*, *Sinapis*, *Solanum*, *Sonchus*, *Sphenoclea*, *Stellaria*, *Taraxacum*, *Thlaspi*, *Trifolium*, *Urtica*, *Veronica*, *Viola*, and *Xanthium*.

[0038] If the compounds of this invention are applied to the soil before germination, germination of weeds is completely prevented, or the weeds are allowed to grow until they reach the cotyledon stage, after which they stop growing and eventually die completely after three to four weeks.

[0039] If the active compound is applied to the green parts of the plant after germination, growth stops after treatment, and the harmful plant remains at the developmental stage at the time of application or dies completely after a period of time, thereby eliminating competition from harmful weeds for the crop plant at a very early and continuous stage.

[0040] While the compounds of this invention exhibit excellent herbicidal activity against both monocot and dicot weeds, the damage to economically important crops is negligible or nonexistent, depending on the structure of the specific compound and its application rate, for example, dicot crops of the following genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, and Tomato. Monocotyledonous crops of the genera *Lycopersicon*, *Nicotiana*, *Phaseolus*, *Pisum*, *Solanum*, *Vicia*, or the genera *Allium*, *Ananas*, *Asparagus*, *Avena*, *Hordeum*, *Oryza*, *Panicum*, *Saccharum*, *Secale*, *Sorghum*, *Triticale*, *Triticum*, and *Zea*, particularly *Zea* and *Wheat*. For these reasons, the compounds of this invention are highly suitable for the selective control of unwanted plant growth in crop plants (e.g., agriculturally useful plants or ornamental plants).

[0041] Furthermore, the compounds of this invention (depending on their specific structure and application rate) exhibit outstanding growth-regulating properties in crop plants. They are able to regulate the plant's own metabolism and can therefore be used to control effects on plant composition and promote yield, for example, by inducing dehydration and inhibiting growth. In addition, they are also suitable for the general prevention and inhibition of unwanted vegetative growth without causing plant death. Inhibition of vegetative growth plays a very important role in many monocotyledonous and dicotyledonous crops because, for example, it can reduce or completely prevent lodging.

[0042] Due to their herbicidal and plant growth-regulating properties, the active ingredients can also be used to control harmful plants in transgenic plants or plants modified through conventional mutations. Transgenic plants often possess particularly advantageous properties, such as resistance to certain pesticides, especially herbicides, and resistance to plant diseases or pathogens that cause them, such as certain insects or microorganisms, like fungi, bacteria, or viruses. Other specific properties relate to, for example, the yield, quality, storability, composition, and specific components of the harvest. For instance, some transgenic plants are known to have increased starch content or altered starch quality, or their harvests may have different fatty acid compositions.

[0043] With regard to genetically modified crops, the compounds of the present invention are preferably used in economically valuable genetically modified crops, both useful and ornamental, such as cereals like wheat, barley, rye, oats, millet, rice, and corn, as well as sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other types of vegetable crops. The compounds of the present invention are preferably used as herbicides in useful plant crops that are resistant to the phytotoxic effects of herbicides or have been genetically engineered to be resistant.

[0044] Conventional methods for preparing new plants with improved characteristics compared to known plants include, for example, conventional breeding methods and mutant generation methods. Alternatively, new plants with improved characteristics can be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following cases have been described in several instances: - By genetically modifying crop plants, the aim is to alter the starch synthesized in the plant (e.g., WO 92 / 11376, WO 92 / 14827, WO 91 / 19806). -Transgenic crop plants resistant to specific glufosinate herbicides (see, for example, EP-A-0242236, EP-A-0242246), gluphosate herbicides (WO 92 / 00377), or sulfonylurea herbicides (EP-A-0257993, US-A-5013659). - Genetically modified crops that produce Bt toxins, making them resistant to specific pests, such as cotton (EP-A-0142924, EP-A-0193259). - A transgenic crop plant with altered fatty acid composition (WO 91 / 13972). - Genetically modified crop plants with new components or secondary metabolites, such as new phytotoxicants that can bring enhanced disease resistance (EPA 309862, EPA0464461). - Genetically modified plants with reduced photorespiration exhibit higher yields and greater stress tolerance (EPA 0305398). - Genetically modified crop plants that produce important proteins for medicinal or diagnostic purposes (“molecular farms”). - Genetically modified crops with higher yields or better quality - Genetically modified crops with combinations of novel properties, such as those described above (“gene stacking”).

[0045] In principle, many molecular biotechnologies are known that can be used to produce new transgenic plants with improved properties; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer LabManual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431.

[0046] For this type of gene manipulation, nucleic acid molecules capable of generating mutations or altering sequences through DNA recombination can be introduced into plasmids. Standard methods can be used to perform, for example, base substitutions, removal of partial sequences, or addition of natural or synthetic sequences. To link DNA fragments together, adapters or linkers can be attached to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., ColdSpring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker, “Gene und Klone” [Genes and Clones], VCH Weinheim, 2nd ed., 1996.

[0047] For example, the generation of plant cells with reduced gene product activity can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a co-repression effect, or by expressing at least one ribozyme with a suitable structure capable of specifically cleaving the transcript of the aforementioned gene product. This can be achieved in two ways: using a DNA molecule containing the complete coding sequence of the gene product—including all possible flanking sequences—or using a DNA molecule containing only a portion of the coding sequence, provided that the portion is long enough to produce an antisense effect in the cell. Alternatively, a DNA sequence that is highly homologous to but not identical to the coding sequence of the gene product can also be used.

[0048] When nucleic acid molecules are expressed in plants, the synthesized proteins can be localized to any desired compartment of the plant cell. However, to achieve localization to a specific compartment, the coding region can be linked, for example, to a DNA sequence that ensures localization in that specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecule expression can also occur within organelles of plant cells.

[0049] Transgenic plant cells can be regenerated using known technologies to produce complete plants. In principle, transgenic plants can be any desired plant species, that is, both monocots and dicots.

[0050] Transgenic plants with altered characteristics can be obtained by overexpressing, repressing, or inhibiting homologous (i.e., natural) genes or gene sequences, or by expressing heterologous (i.e., exogenous) genes or gene sequences.

[0051] Preferably, the compounds of the present invention are used in transgenic crops that are resistant to growth regulators such as dicamba, or to herbicides that inhibit important plant enzymes such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS), or hydroxyphenylpyruvate dioxygenase (HPPD), or to herbicides selected from sulfonylureas, glyphosate, glufosinate, or benzoylisoxazole and similar active ingredients.

[0052] When the active ingredients of this invention are used in genetically modified crops, in addition to the effects on harmful plants that can be observed in other crops, there are usually special effects on specific genetically modified crops, such as altering or specifically expanding the spectrum of weeds that can be controlled, altering the amount that can be applied, better compatibility with herbicides that are resistant to genetically modified crops, and effects on the growth and yield of genetically modified crop plants.

[0053] Therefore, the present invention also relates to the use of compounds of formula (I) and / or salts thereof as herbicides for the control of harmful plants in crops of useful or ornamental plants, optionally in genetically modified crops.

[0054] The present invention also includes the use of the active compound of formula (I) or its salts not formed from a precursor (“prodrug”), but formed after application to the plant, within the plant or soil.

[0055] The present invention also provides the use of one or more compounds of formula (I) or salts thereof or compositions thereof according to the present invention (as defined below) for the control of harmful plants or for the regulation of plant growth, comprising applying an effective amount of one or more compounds of formula (I) or salts thereof to plants (harmful plants, if applicable, together with beneficial plants), plant seeds, soil or cultivated areas in which plants grow or on which plants grow.

[0056] The present invention also provides a herbicide and / or plant growth regulator composition, characterized in that the composition comprises (a) One or more compounds of formula (I) and / or salts thereof (as defined above), preferably one of the preferred or particularly preferred configurations, in particular one or more compounds of formulas 1-1 to 1-33 and / or salts thereof, in each case as defined above, and (b) One or more other substances selected from (i) and / or (ii): (i) one or more other agricultural chemically active substances, preferably insecticides, acaricides, nematicides, other herbicides (i.e., herbicides different from those of formula (I) above), fungicides, safeners, fertilizers and / or other growth regulators, (ii) One or more formulation adjuvants commonly used in crop protection.

[0057] Other agrochemically active substances in component (i) of the composition of the present invention are preferably selected from those mentioned in “The Pesticide Manual”, 19th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021.

[0058] A herbicide or plant growth regulator composition of the present invention preferably comprises one, two, three or more formulation adjuvants commonly used in crop protection (ii), said formulation adjuvants being selected from surfactants, emulsifiers, dispersants, film-forming agents, thickeners, inorganic salts, dusts, carriers that are solid at 25°C and 1013 mbar (preferably adsorbable particulate inert materials), wetting agents, antioxidants, stabilizers, buffers, defoamers, water, and organic solvents (preferably organic solvents miscible with water in any proportion at 25°C and 1013 mbar).

[0059] The compounds of the present invention can be applied in the form of conventional formulations, such as wettable powders, emulsifiable concentrates, sprayable solutions, dusting products, or granules. Therefore, the present invention also provides herbicidal compositions and plant growth regulating compositions comprising the compounds of the present invention.

[0060] The compounds of the present invention can be formulated in a variety of ways according to desired biological and / or physicochemical parameters. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) (such as oil-in-water emulsions and water-in-oil emulsions), sprayable solutions, suspension concentrates (SC), oil- or water-based dispersants, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), seed dressing products, granules for broadcasting and soil application, granules in the form of microparticles, spray particles, absorbent and adsorbent particles (GR), water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes.

[0061] These various formulation types are known in principle and documented in, for example: Winnacker-Küchler, “Chemische Technologie” [Chemical technology], Volume 7, C. Hanser Verlag, Munich, 4th edition, 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, NY, 1973; K. Martens, “Spray Drying” Handbook, 3rd edition, 1979, G. Goodwin Ltd., London.

[0062] The required formulation adjuvants, such as inert materials, surfactants, solvents, and other additives, are also known and described, for example: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books; Caldwell NJ, H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, NY; C. 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 ethylene oxide] ads], Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-Küchler, “ChemischeTechnologie” [Chemical technology], Volume 7, C. Hanser Verlag Munich, 4th edition 1986.

[0063] Based on these formulations, compositions can also be produced with other insecticidal substances (e.g., insecticides, acaricides, herbicides, fungicides) as well as safeners, fertilizers, and / or growth regulators, for example, in the form of finished formulations or tank mixes. Suitable safener packages include, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, and dichlormid.

[0064] Wettable powders are formulations that can be uniformly dispersed in water and, in addition to the active ingredient and diluents or inert substances, contain ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyoxyethylene alkylphenols, polyoxyethylene fatty alcohols, polyoxyethylene fatty amines, fatty alcohol polyethylene glycol ether sulfates, alkyl sulfonates, alkylbenzene sulfonates, sodium lignin sulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene sulfonate, or sodium oleoylmethyl taurate. To prepare wettable powders, the active herbicidal ingredient is finely ground, for example, in conventional equipment (e.g., hammer mill, blower mill, and air jet mill), and simultaneously or subsequently mixed with formulation adjuvants.

[0065] Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent (e.g., butanol, cyclohexanone, dimethylformamide, xylene, or a higher-boiling aromatic compound or hydrocarbon) or a mixture of organic solvents, and adding one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that may 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, sorbitan esters (e.g., sorbitan fatty acid esters), or polyoxyethylene sorbitan esters (e.g., polyoxyethylene sorbitan fatty acid esters).

[0066] Powdered products are obtained by grinding active ingredients together with finely dispersed solid substances, such as talc, natural clay (e.g., kaolin, bentonite, and pyrophyllite), or diatomaceous earth.

[0067] Suspension concentrates can be water-based or oil-based. They can be prepared, for example, by wet milling using a commercially available bead mill and optionally by adding a surfactant, such as those listed in the other formulation types above.

[0068] Emulsions, such as oil-in-water emulsions (EW), can be prepared, for example, by a mixer, colloid mill, and / or static mixer, using an aqueous organic solvent and optionally a surfactant, which has been listed above, for example, in other formulation types.

[0069] 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 a binder (such as polyvinyl alcohol, sodium polyacrylate, or mineral oil). Suitable active ingredients can also be granulated in a manner commonly used to prepare fertilizer granules (if necessary, mixed with fertilizer).

[0070] Water-dispersible granules are typically prepared using conventional methods such as spray drying, fluidized bed granulation, disc granulation, mixing with a high-speed mixer, and extrusion without solid inert materials.

[0071] For the preparation of disc particles, fluidized bed particles, extruded particles, and sprayed particles, see, for example, the methods in the following literature: “Spray-Drying Handbook”, 3rd edition, 1979, G. Goodwin Ltd., London, JEBrowning, “Agglomeration”, Chemical and Engineering 1967, from page 147; “Perry’s Chemical Engineer’s Handbook”, 5th edition, McGraw-Hill, New York 1973, pp. 8-57.

[0072] For further details on the formulation of crop protectants, see, for example, GC Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pp. 81–96 and JD Freyer, SA Evans, “Weed Control Handbook”, 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101–103.

[0073] Agricultural chemical formulations typically contain 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the compounds of the present invention.

[0074] In wettable powders, the concentration of the active ingredient is, for example, about 10 to 90% by weight, with the remainder, up to 100% by weight, consisting of conventional formulation components. In emulsifiable concentrates, the concentration of the active ingredient can be about 1 to 90% by weight, and preferably 5 to 80% by weight. Powdered formulations contain 1 to 30% by weight of the active ingredient, typically preferably 5 to 20% by weight; sprayable solutions contain about 0.05 to 80% by weight, preferably 2 to 50% by weight of the active ingredient. In the case of water-dispersible granules, the content of the active ingredient depends in part on whether the active ingredient is in liquid or solid form, and on the granulation aids, fillers, etc., used. In water-dispersible granules, the content of the active ingredient is, for example, 1 to 95% by weight, preferably 10 to 80% by weight.

[0075] In addition, the active ingredient formulations mentioned may optionally include corresponding conventional binders, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors, and additives that affect pH and viscosity. Examples of formulation adjuvants are particularly documented in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).

[0076] The compounds of formula (I) or their salts may be used alone or in combination with other insecticidal substances (e.g., insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and / or growth regulators) in the form of formulations, such as finished formulations or tank mixes. The formulations may be produced based on the above formulations, taking into account the physical properties and stability of the active ingredient to be bound.

[0077] Of particular interest is the selective control of harmful plants in beneficial and ornamental crops. Although the compound (I) of this invention has shown good to sufficient selectivity in a variety of crops, phytotoxicity may still occur in certain crops, especially when mixed with other less selective herbicides. In this regard, combinations of the compound (I) of this invention, comprising the compound (I) or combinations thereof with other herbicides or insecticides and safeners, are of particular interest. Safeners used at an effective dose to detoxify reduce the phytotoxic side effects of the applied herbicide / insecticide, for example in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beets, sugarcane, rapeseed, cotton, and soybeans, with cereals being preferred.

[0078] The weight ratio of herbicide (mixture) to safener typically depends on the application rate of the herbicide and the efficacy of the associated safener, and can vary widely, for example, from 200:1 to 1:200, preferably from 100:1 to 1:100, and particularly from 20:1 to 1:20. Similar to compound (I) or mixtures thereof, the safener can be formulated with other herbicides / insecticides and supplied and used together with the herbicide in the form of a finished formulation or a tank-mixture.

[0079] For application, if appropriate, commercially available herbicide formulations or herbicide-safety formulations are diluted using conventional methods, such as water in the case of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Powdered formulations, granules for soil application or broadcasting, and sprayable solutions do not require further dilution with other inert substances before normal application.

[0080] The application rate of the compound of formula (I) and / or its salts is affected to some extent by external conditions such as temperature and humidity. The application rate can vary within a wide range. When used as a herbicide to control harmful plants, the total amount of the compound of formula (I) and its salts is preferably 0.001 to 10.0 kg / ha, more preferably 0.005 to 5 kg / ha, more preferably 0.01 to 1.5 kg / ha, and particularly preferably 0.05 to 1 kg / ha. This application rate is suitable for application before or after emergence.

[0081] When the compounds of formula (I) and / or their salts are used as plant growth regulators, for example as stem stabilizers for the aforementioned crops (preferably cereal crops such as wheat, barley, rye, triticale, millet, rice, or maize), the preferred total application rate is 0.001 to 2 kg / ha, more preferably 0.005 to 1 kg / ha, especially 10 to 500 g / ha, and very particularly preferably 20 to 250 g / ha. This is suitable for application before or after emergence.

[0082] Application as a stem stabilizer can be carried out at different stages of plant growth. Preferred application is, for example, after tillering or at the early stage of longitudinal growth.

[0083] Alternatively, plant growth regulators can be applied through seed treatment, which includes various techniques for seed coating and seed plating. The application rate depends on the specific technique and can be determined in preliminary trials.

[0084] In mixtures or tank mixes, the conjugating agents that can be used in combination with compounds of formula (I) are, for example, known active ingredients that inhibit, for example, the following enzymes: acetolactate synthase, acetyl-CoA carboxylase, cellulase, enolpyruvate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, or protoporphyrinogen oxidase, or known active ingredients that act as plant growth regulators, for example, see Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 19th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021, and the references cited therein.

[0085] Examples of known herbicides or plant growth regulators that can be combined with compounds of general formula (I) include the active ingredients listed below (these compounds are represented by their common name or chemical name or code number from the International Organization for Standardization (ISO)) and they always cover all forms of use, such as acids, salts, esters, and isomers such as stereoisomers and optical isomers. This list includes, for example, one application form and, in some cases, multiple application forms: Acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicabazon, amidochlor, amidosulfuron, 4-amino 3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-dimethylammonium, aminopyralid-tripromine, amitrol, ammonia Ammonium sulfonate, ailofos, asulam, asulam-potassium, asulamsodium, atrazin, azafenidin, azimsulfuron, beflubutamid, (S)-(-)-beflubutamid, beflubutamid-M, benzolin, benzolin-ethyl, benzolin-dimethylammonium Herbicides including in-dimethylammonium, benzolin-potassium, benzfluralin, benzuresate, benzsulfuron, benzsulfuron-methyl, benzulid, betazon, betazon-sdium, benzobicyclon, benzofenap, bicyclopyrone, and bifenox.Bilanamfos, bilanafos-sodium, bipyrazone, bispyribac, bispyribac-sodium, bixlozon, bromacil, bromacil-lithium, bromacil-sodium, bromobutid, bromofenoxim, bromoxynil, bromoxynil- Butyrat, bromoxynil-potassium, bromoxynil-heptanoate, and bromoxynil-octanoate, busoxinon, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylat, cafenstrol, and cambe ndichlor, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium, chloramben-sodium, chlorbromide uron), chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalimChlortoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cycloheptane (i.e., (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane), exo-(-)-cycloheptane (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, cromazine, clonateprop, clopyralid, clopyralid-methyl, clopyralid ethanolamine (clopyralid-olamine), clopyralid-potassium, clopyralid-tripomine, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloat, cyclopyranil, cyclopyrimorat, cyclosulfamuron, cycloxydim, cyhalofop Cyhalofop-butyl, cyprazine, 2,4-D (and its ammonium salts), 2,4-D-butoxyethyl ester (2,4-D-butoyl), 2,4-D-butyl ester, 2,4-D-choline, 2,4-D-diethylammonium, 2,4-D-dimethylammonium, 2,4-D-diolamine, 2,4-D-doboxyl, 2,4-D-dodecylammonium, 2,4-D-etexyl, 2,4-D-ethyl ester, 2,4-D-2-ethylhexyl ester, 2,4-D-heptylammonium, 2,4-D-isobutyl ester, 2,4-D-isooctyl ester, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-lithium,2,4-D-meptyl, 2,4-D-methyl ester, 2,4-D-potassium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-triisopropanolammonium, 2,4-D-tripromine and 2,4-D-trolamine salts), 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium, 2,4-DB-isooctyl ester, 2,4-DB-potassium and 2,4-DB-sodium, daimuron (dymron), dalapon, dalapon-calcium salt, dalapon magnesium salt (dalapon) pon-magnesium, dalapon-sodium, dazomet, dazomet-sodium, n-decyl alcohol, 7-deoxy-D-sedoheptulose, desmedipham, detosyl-pyrazolate (DTP), dicamba and its salts (e.g., dicamba-biproamine, dicamba-N,N-bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline). α-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolaminemmonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolamine, dicamba Dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine, 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, and dichlorprop-butotyl.Dichlorprop-dimethylammonium, dichlorprop-etexyl, dichlorprop-ethylammonium, dichlorprop-isooctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-protic acid p-P), dichlorprop-P-dimethylammonium, dichlorprop-P-etexyl, dichlorprop-P-potassium, dichlorprop-sodium, diclofop, diclofop-methyl, diclofop-P, diclofop-P-methyl, diclosulam, difenzoqua t), Difenzoquat-metilsulfate, Diflufenican, Diflufenzopyr, Diflufenzopyr-sodium, Dimefuron, Dimepiperate, Dimesulfazet, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimetrasulfuron Disinfectant (dinitramine), 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, Ethalfluralin, Ethametsulfuron, Ethametsulfuron-methyl, Ethiozin, Ethofumesate, Ethoxyfen, Ethoxyfen-ethyl, Ethoxysulfuron, Etobenzanid, 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-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidin-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxaprop-P-ethyl, fenoxaprop-sulfuron (fenoxasulfone), fenpyrazone, fenquinotrione, fentrazamide, flamprop, flamprop-isoproyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasul am), florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuronFluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium, flurenol-methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, and flupropanaate sodium salt. e-sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridon, flurochloridon, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurtamon, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, foramsulfuron-sodium. Sodium glufosinate, 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 sesquisodium and glyphosate-trimesium, H-9201 (O-(2,4-dimethyl-6-nitrophenyl)-O-ethylisopropylphosphoramidothioate), halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-methyl, haloxyfop-ethoxyethyl. p-P-methyl), haloxifop-sodium, hexazinon, HNPC-A8169 (i.e., (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propionate prop-2-yn-1-yl ester), HW-02 (i.e., 1-(dimethoxyphosphoryl)-ethyl-(2,4-dichlorophenoxy)acetic acid ester), hydantocidin, icafolin, icafolin-methy l), imidacloprid (imazamethabenz), methyl imidacloprid (imazamethabenz-methyl), imazamox (imazamox), imazamox-ammonium (imazamox-ammonium), imazapic (imazapic-ammonium), imazapyr (imazapyr-isopropylammonium), imazaquin (imazaquin)Imidazolium-ammonium, methyl imazaquin, imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, indolauxipyr, iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-s The following are listed: sodium, iooxynil, lithium iooxynil, iooxynil-octanoate, potassium iooxynil, sodium iooxynil, ipfencarbazone, iptriazopyrid (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), and isoproturon. Isouron, isoxaben, isoxaflutole, karbutilate, KUH-043 (i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, ketospiradox-potassium, lactoferrin, lenacil, linuron, MC PA, MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diethanolamine, MCPA-2-ethylhexyl, MCPA-ethyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methylMCPA-olamine, MCPA-potassium, MCPA-sodium, and MCPA-trolamine, MCPB, MCPB-methyl, MCPB-ethyl, and MCPB-sodium, 2-methyl-4-chloropropionic acid, 2-methyl-4-chloropropionic acid butoxyethyl ester, and 2-methyl-4-chloropropionic acid dimethylammonium. (The following are listed as unrelated to the previous sentence and likely represent separate, likely machine-translated text fragments): mmonium, diethanolamine 2-methyl-4-chloropropionate, mecoprop-etexyl, mecoprop-ethadyl, isooctyl 2-methyl-4-chloropropionate, methyl 2-methyl-4-chloropropionate, potassium 2-methyl-4-chloropropionate, sodium 2-methyl-4-chloropropionate, triethanolamine 2-methyl-4-chloropropionate, purified 2-methyl-4-chloropropionic acid (mecoprop...) (The following are listed as unrelated terms: rop-P), mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidid, mefluidide-diolamine, mefl) (The following are listed as examples of herbal products): uidide-potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron-sodium, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, and methabenzthiazuron.Methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metproxybicyclon, metribuzin, metsulfuron-methyl, molinat, chlorpyrifos Nolinuron, monosulfuron, monosulfuron-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), neburon, nicosulfuron, pelargonic acid acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat dichlorvos dichloride, paraquat-dimethylsulfate, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, mineral oil, phenmedipham, phenmedipham-ethyl, picloram, picloram-dimethylammonium, picloram-etexyl, picloram-isoctyl, picloram-methylPicloram-olamine, picloram-potassium, picloram-triethylammonium, picloram-tripromine, picloram-trolamine, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisul furon-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron n), propyzamid, prosulfocarb, prosulfuron, pyraclonil, piraflufen, pyraflufen-ethyl, pyraquinat, pyrasulfotol, pyrazolynate (pyrazolat), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen. ribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridat, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfonPyroxsulam, quinclorac, quinclorac-dimethylammonium, quinclorac-methyl (methyl quinclorac), quinmerac, quinoclamin, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-Tefuryl, QYM201 (i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one), rimisoxafen, rimsulfuron ron), saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfonyl Sulfosulfuron, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), SYP-300 (i.e., 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 (such as ammonium trichloroacetate, calcium trichloroacetate, ethyl trichloroacetate, magnesium trichloroacetate, sodium trichloroacetate), tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thaxtomin, thenylchlor, thiazopyr, thiencarbazoneThiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, toramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron-methyl, tribensulfuron, tribensulfuron-methyl, triclopyr, triclopyr-methyl Trilopyr-butotyl, triclopyr-choline, triclopyr-ethyl, triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate sulfate), Vernolate, XDE-848, ZJ-0862 (i.e., 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-dihydroxypyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5-carboxylic acid ethyl ester, 3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl- [3,6-Dihydropyrimidin-1(2H)-yl)phenyl]-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, 3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl]-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid, [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]ethyl acetate,3-Chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl-5-chloropyrimidin-2-yl ether, 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-dioxide-2,3-dihydro-1-benzothiophene-5-yl) methyl ketone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophene-5-yl)carbonyl] [4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl]-1-methyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazol-4-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate cyanomethyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate prop-2-ynyl 1-yl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate methyl ester, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate methyl ester, 4-amino-3-chloro-5-fluoro-6-yl)pyridine-2-carboxylate Benzyl 4-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, 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)-1H- Methyl indole-6-yl]pyridin-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridin-2-carboxylate, sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridin-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridin-2-carboxylate, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolin-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolin-2-one4-Hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolin-2-one, 6-[(2-hydroxy-6-oxocyclohexyl-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazolin-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohexyl-1-en-1-yl)carbonyl]-1-methylquinazolin-2,4(1H,3H)-dione, 2-[2-chloro-4-(methanesulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohexyl-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)-2-yl)-2-yl)-3-hydroxycyclohexyl-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)-3-yl)-4 ... 1-(2-Carboxyethyl)-4-(pyrazin-3-yl)pyrazin-1-onium salts (with suitable anions, such as chloride, acetate, or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyrazin-1-onium salts (with suitable anions, such as chloride, acetate, or trifluoroacetate), 4-(pyrazin-3-yl)-1-(2-sulfoethyl)pyrazin-1-onium salts (with suitable anions, such as chloride, acetate, or trifluoroacetate), 1-(2-Carboxyethyl)-4-(1,3-thiazolyl-2-yl ... (e.g., chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3,4-thiadiazol-2-yl)pyridazine-1-onium salt (with a suitable anion, such as chloride, acetate or trifluoroacetate), (2R)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylene)amino]oxy}methyl propionate, (2S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylene)amino] Methyl propionate, (2R / S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}methylene)amino]oxy}methyl propionate, (E)-2-(trifluoromethyl)benzaldehyde O-{2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoyl}oxime, 2-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]propanecarboxylic acid,2-Ethoxy-2-oxoethyl-1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropane carboxylate, 2-methoxy-2-oxoethyl-1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropane carboxylate, {[(1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-... -(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2-bromo-4-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopentane[d][1,2]oxazol-6a-carboxylic acid methyl ester, 3-{2-chloro-4-fluoro-5-[3 3-{methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopentano[d][1,2]oxazol-6a-carboxylic acid ethyl ester, 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-6-methyl-3a,4,5,6-tetrahydro-6aH-cyclopentano[d][1,2]oxazol-6a-carboxylic acid methyl ... 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-6-methyl-3a,4,5,6-tetrahydro-6aH-cyclopentano[d][1,2]oxazol-6a-carboxylic acid, 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopentano[d][1,2]oxazol-6a-carboxylic acid, 、

[0086] Abscisic acid and its analogues [e.g., (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohexyl-2-en-1-yl]-3-methylpent-2,4-dienoic acid, (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohexyl-2-en-1-yl]-3-methylpent-2,4-dienoic acid methyl ester, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohexyl-2-en-1-yl)pent-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohexyl-2-en-1-yl)pent-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohexyl-2-en-yl)pent-2,4-dienoic acid, ...] (1-yl)-3-(trifluoromethyl)pent-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)pent-2,4-dienoic acid methyl ester, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpent-2,4-dienoic acid, acibenzolar, acibenzolar-S-methyl, S-adenosylhomocyline Steine), allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g., (isopropylidene)aminooxyacetic acid 2-(methoxy)-2-oxoethyl ester, (isopropylidene)aminooxyacetic acid 2-(hexyloxy)-2-oxoethyl ester, (cyclohexylene)aminooxyacetic acid 2-(isopropyloxy)-2-oxoethyl ester], 1-aminocyclopropyl-1-ylcarboxylic acid, N-methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, substituted 1-aminocyclopropyl-1-carboxylic acid as described in DE3335514, EP30287, DE2906507 or US5123951 Propyl-1-carboxylic acid derivatives, 1-aminocyclopropyl-1-hydroxyamine, 5-aminolevulinic acid, pyrimidinol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, L-canaline, catechols and catechins (e.g., (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-benzopyran-3,5,7-triol), chitosan oligosaccharides (CO; CO differs from LCO in that it lacks fatty acid side chains, which are characteristic of LCO).CO, sometimes also called N-acetylated chitosan oligosaccharides, is also composed of GlcNAc units, but has side chains that distinguish it from chitin [(C8H13NO5)n, CAS No. 1398-61-4] and chitosan [(C5H11NO4)n, CAS No. 9012-76-4], chitin-like compounds, and chlormequat chloride. chloride), cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozid, dazomet, dazomet-sodium, n-decanol, dikegulac, dikegulac-sodium, endopyric acid othal), endothal-dipotassium, endothal-disodium, and mono(N,N-dimethylalkylammonium), ethephon, 1-ethylcyclopropene, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid acid), antidoteamine (inabenfide), indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprethiolan, probenazole, jasmonic acid, jasmonic acid and its derivatives (such as methyl jasmonic acid, ethyl jasmonic acid), lipochokines (LCO, sometimes also called symbiotic nodulation signal (Nod or Nod factor) or Myc factor, which consists of an oligosaccharide backbone with β-l,4-linked N-acetyl-D-glucosamine groups ("GlcNAc") having N-linked fatty acid side chains condensed at non-reducing ends.Based on the literature, it can be inferred that the differences in LCO lie in the number and length of GlcNAc groups in its skeletal structure, the saturation of the fatty acid chain, and the substitution of reducing and non-reducing sugar portions. Other components include linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazine, mepiquat chloride, mepiquatpentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinoline-6-yl)methanesulfonamide and related substituted (tetrahydroquinoline-6-yl)methanesulfonamides, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H- Indo[1,2-b]furan-2-one and related lactones described in EP2248421, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthoxyacetic acid, nitrophenoxide mixture, 4-oxo-4-[(2-phenylethyl)amino]butyric acid, paclobutrazole, 4-phenylbutyric acid and its salts (e.g., sodium phenylbutyrate, potassium phenylbutyrate), phenylalanine, N-phenyl-o-carbamoylbenzoic acid, prohexadione, prohexadione-cal cium), 1-n-propylcyclopropene, putrescine, prohydrojasmone, rhizobitoxin, salicylic acid, methyl salicylate, sarcosine, sodium cycloprop-1-en-1-acetate, sodium cycloprop-2-en-1-acetate, sodium 3-(cycloprop-2-en-1-yl)propionate, sodium 3-(cycloprop-1-en-1-yl)propionate, sidefungin, spermidine, spermine, strigolactone tone), tetrachloronitrobenzene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine, 2-chloro-N-(3-methoxyphenyl)-9H-purine-6-amine.

[0087] The same applies to safety agents used as binding agents for compounds of formula (I), including, for example: Compounds of formula (S1), The symbols and subscripts are defined as follows: n A The range is 0 to 5, preferably 0 to 3 (natural numbers); R A 1 It is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro, or (C1-C4)-haloalkyl; W A It is an unsubstituted or substituted divalent heterocyclic group selected from partially unsaturated or aromatic five-membered heterocycles having 1 to 3 cyclic heteroatoms selected from N and O, wherein at least one nitrogen atom and at most one oxygen atom are present in the ring, preferably selected from (W A 1 ) to (W A 5 ) group, m A It can be 0 or 1; R A 2 OR A 3 SR A 3 or NR A 3 R A 4 Or a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to three heteroatoms (preferably selected from O and S), which is linked to a carbonyl group in (S1) via a nitrogen atom and is unsubstituted or substituted with a group selected from: (C1-C4)-alkyl, (C1-C4)-alkoxy, or optionally substituted phenyl, preferably of formula OR A 3 NHR A 4 or N(CH3)2 groups, especially those of the formula OR A 3 Groups; R A 3 It is a hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group having a total of 1 to 18 carbon atoms; R A 4 It is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, or a substituted or unsubstituted phenyl group; RA 5 It is H, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, cyano, or COOR. A 9 , where R A 9 It is hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-hydroxyalkyl, (C3-C 12 )-cycloalkyl or tri-(C1-C4)-alkylsilyl; R A 6 R A 7 R A 8 They may be the same or different, and each is hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C8)-alkyl, or (C1-C8)-alkyl-halogenated. 12 )-Cycloalkyl or substituted or unsubstituted phenyl; R A 10 For H, (C3-C 12 )-cycloalkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl; Preferred: a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid class (S1) a Preferred compounds include, for example, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid (S1-1) (“mefenpyr-diethyl”), and related compounds as described in WO-A-91 / 07874; b) Derivatives of dichlorophenylpyrazole carboxylic acid (S1) b Preferred compounds include, for example, ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4), and related compounds, as described in EP-A-333131 and EP-A-269 806; c) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1) cPreferred compounds include, for example, ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6), and related compounds, such as those described in EP-A-268 554. d) Triazole carboxylic acid compounds (S1) d Preferred compounds include, for example, ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-7), and related compounds, such as those described in EP-A-174 562 and EP-A-346 620; e) Compounds of the class 5-benzyl-2-isooxazoline-3-carboxylic acid, 5-phenyl-2-isooxazoline-3-carboxylic acid, or 5,5-diphenyl-2-isooxazoline-3-carboxylic acid (S1) e Preferred compounds include, for example, ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds, as described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) (“isoxadifen-ethyl”) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), as described in patent application WO-A-95 / 07897; f) Triazolyloxyacetic acid derivative type (S1) fPreferred compounds include, for example, methyl acetate {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-14), methyl acetate {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-15), methyl acetate {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-16), or methyl acetate {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy}acetate (S1-17). Or methyl acetate {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy} (S1-18) or {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy} acetic acid (S1-19), as described in patent application WO2021 / 105101.

[0088] Quinoline derivatives of formula (S2), The symbols and subscripts are defined as follows: R B 1 It is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro, or (C1-C4)-haloalkyl; n B The range is 0 to 5, preferably 0 to 3 (natural numbers); R B 2 OR B 3 SR B 3 or NR B 3 R B 4 A 3- to 7-membered heterocycle, either saturated or unsaturated, having at least one nitrogen atom and up to three heteroatoms (preferably selected from O and S), the heterocycle being linked to a carbonyl group in (S2) via a nitrogen atom and being unsubstituted or substituted with a group selected from: (C1-C4)-alkyl, (C1-C4)-alkoxy, or optionally substituted phenyl, preferably of the formula OR. B 3 NHR B 4 or N(CH3)2 groups, especially those of the formula OR B 3 Groups; R B3 It is hydrogen or preferably an unsubstituted or substituted aliphatic hydrocarbon group having a total of 1 to 18 carbon atoms; R B 4 It is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, or a substituted or unsubstituted phenyl group; T B It is a (C1 or C2)-alkidine chain, which is unsubstituted or substituted with one or two (C1-C4)-alkyl groups or substituted with [(C1-C3)-alkoxy]carbonyl groups; Preferred: a) Compounds of the 8-quinolinoxyacetic acid class (S2) a Preferred (5-Chloro-8-quinolinoxy)acetic acid 1-methylhexyl ester ("cloquintocet-mexyl") (S2-1), (5-Chloro-8-quinolinoxy)acetic acid 1,3-dimethylbut-1-yl ester (S2-2), (5-Chloro-8-quinolinoxy)acetic acid 4-allyloxybutyl ester (S2-3), (5-Chloro-8-quinolinoxy)acetic acid 1-allyloxypropyl-2-yl ester (S2-4), Ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), (5-Chloro-8-quinolinoxy)methyl acetate (S2-6), (5-Chloro-8-quinolinoxy)acetic acid allyl ester (S2-7), (5-Chloro-8-quinolinoxy)acetic acid 2-(2-propyliminooxy)-1-ethyl ester (S2-8), (5-chloro-8-quinolinoxy)acetic acid 2-oxopropyl-1-yl ester (S2-9) and related compounds, as described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366, and (5-chloro-8-quinolinoxy)acetic acid (S2-10) and its hydrates and salts, such as its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as described in WO-A-2002 / 34048; b) Compounds of (5-chloro-8-quinolinoxy)malonic acid (S2) b Preferred compounds include, for example, diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate, and related compounds, as described in EP-A-0 582 198.

[0089] Compounds of formula (S3) The symbols and subscripts are defined as follows: R C 1 It is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl; R C 2 R C 3 They are the same or different, and each is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-haloalkyl, (C2-C4)-haloalkenyl, (C1-C4)-alkylcarbamoyl-(C1-C4)-alkyl, (C2-C4)-alkenylcarbamoyl-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, dioxanepentyl-(C1-C4)-alkyl, thiazolyl, furanyl, furanylalkyl, thiophene, piperidinyl, substituted or unsubstituted phenyl, or R C 2 and R C 3Together they form substituted or unsubstituted heterocycles, preferably oxazolidine, thiazolidinidine, piperidine, morpholine, hexahydropyrimidine, or benzoxazine rings; preferably: dichloroacetamide-type active ingredients, which are often used as pre-emergence safeners (safeners acting on the soil), such as "dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), purchased from Stauffer; "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2), purchased from Stauffer; "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3), purchased from Stauffer; and "benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), purchased from PPG. PPG-1292 (N-allyl-N-[(1,3-dioxolane-2-yl)methyl]dichloroacetamide) (S3-5) from Industries; DKA-24 (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6) from Sagro-Chem; AD-67 or MON 4660 (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (S3-7) from Nitrokemia or Monsanto; TI-35 (1-dichloroacetylazacycloheptane) (S3-8) from TRI-Chemical RT; and diclonon (dicyclonone), BAS145138, or LAB145138 from BASF. (S3-9) ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one), "furilazole" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-11).

[0090] N-acylsulfonamides of formula (S4) and their salts. The symbols and subscripts are defined as follows: X D For CH or N; R D 1 CO-NR D 5 R D 6 or NHCO-R D 7 ; R D 2 It is a halogen, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl; R D 3 It is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, or (C2-C4)-alkynyl; R D 4 It can be halogen, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-haloalkoxy, (C3-C6)-cycloalkyl, phenyl, (C1-C4)-alkoxy, cyano, (C1-C4)-alkylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl or (C1-C4)-alkylcarbonyl; R D 5 It is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-ynyl, (C5-C6)-cycloalkenyl, phenyl, or contains v D Three to six heterocyclic groups selected from nitrogen, oxygen, and sulfur heteroatoms, wherein the last seven groups are v D The substituent is selected from the following: halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl and phenyl, and in the case of a cyclic group, also selected from (C1-C4)-alkyl and (C1-C4)-haloalkyl; R D 6 It is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, or (C2-C6)-ynyl, wherein the last three groups are v D The substituted group is selected from the following groups: halogen, hydroxyl, (C1-C4)-alkyl, (C1-C4)-alkoxy, and (C1-C4)-alkylthio, or R D 5 and R D 6 Together with their nitrogen atoms, they form pyrrolidinyl or piperidinyl groups; R D 7It is hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, wherein the last two groups are v D The substituent is selected from the following: halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio, and in the case of a cyclic group, also selected from (C1-C4)-alkyl and (C1-C4)-haloalkyl. n D It can be 0, 1, or 2; m D It can be 1 or 2; v D It can be 0, 1, 2, or 3; Among them, N-acylsulfonamide compounds are preferred, such as those of the following formula (S4) a Compounds of which, for example, are known by WO-A-97 / 45016, in R D 7 It is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, wherein the last two groups are v D The substituent is selected from the following: halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy and (C1-C4)-alkylthio, and in the case of a cyclic group, also selected from (C1-C4)-alkyl and (C1-C4)-haloalkyl. R D 4 Halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3; m D It can be 1 or 2; v D It can be 0, 1, 2, or 3; as well as Acylaminosulfonylbenzamides, such as those with the following formula (S4) b Compounds of which, for example, are known by WO-A-99 / 16744, For example, those compounds, in which R D 5 =Cyclopropyl and (R) D 4 ) = 2-OMe ("cyprosulfamide", S4-1) R D 5=Cyclopropyl and (R) D 4 ) = 5-Cl-2-OMe (S4-2), R D 5 =Ethyl and (R) D 4 ) = 2-OMe (S4-3), R D 5 =Isopropyl and (R) D 4 ) = 5-Cl-2-OMe (S4-4), and R D 5 =Isopropyl and (R) D 4 ) = 2-OMe (S4-5) as well as N-acylaminosulfonylphenylurea compounds, formula (S4) c Compounds of which, for example, are known from EP-A-365484, in R D 8 and R D 9 Independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-ynyl, R D 4 Halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3, m D It can be 1 or 2; For example 1-[4-(N-2-methoxybenzoylaminosulfonyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylaminosulfonyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylaminosulfonyl)phenyl]-3-methylurea.

[0091] S5) Active ingredients derived from hydroxy aromatic compounds and aromatic-aliphatic carboxylic acid derivatives, such as ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, and WO-A-2005 / 016001.

[0092] S6) is an active ingredient derived from 1,2-dihydroquinoxaline-2-ones, such as... 1-Methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005 / 112630.

[0093] Compounds of formula (S7), such as those described in WO-A-1998 / 38856, The symbols and subscripts are defined as follows: R E 1 R E 2 Independently, it is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, or nitro. A E For COOR E 3 or COSR E 4 ; R E 3 R E 4 Each of these can be independently hydrogen, (C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C4)-alkynyl, cyanoalkyl, (C1-C4)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridylalkyl, and alkylammonium. n E 1 It can be 0 or 1. n E2 n E 3 Independently 0, 1, or 2, Preferred ingredients include diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, and methyl diphenylmethoxyacetate (CAS Registry No. 41858-19-9) (S7-1).

[0094] Compounds of formula (S8) or salts thereof, as described in WO-A-98 / 27049. in X F For CH or N, n F In X F = N is an integer from 0 to 4, and In X F = CH is an integer from 0 to 5. R F 1 Halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, nitro, (C1-C4)-alkylthio, (C1-C4)-alkylsulfonyl, (C1-C4)-alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy R F 2 It is hydrogen or (C1-C4)-alkyl. R F 3 It is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, wherein each of the carbon-containing groups mentioned above is unsubstituted or substituted by one or more, preferably up to three identical or different groups selected from halogens and alkoxy groups. The following compounds or their salts are preferred, wherein X F For CH, n F Integers between 0 and 2 R F 1 It is a halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, or (C1-C4)-haloalkoxy. R F 2 It is hydrogen or (C1-C4)-alkyl. R F 3It is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, wherein each of the above carbon-containing groups is unsubstituted or substituted by one or more, preferably up to three identical or different groups selected from halogens and alkoxy groups.

[0095] S9) refers to active ingredients derived from the 3-(5-tetrazolylcarbonyl)-2-quinolone class, such as 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Registry No. 219479-18-2) and 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Registry No. 95855-00-8), as described in WO-A-1999 / 000020.

[0096] S10) formula (S10) a ) or (S10 b ) compounds As described in WO-A-2007 / 023719 and WO-A-2007 / 023764, in R G 1 Halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3, Y G Z G Each can be either O or S, independent of the others. n G Integers from 0 to 4 R G 2 For (C1-C 16 (C2-C6)-alkyl, (C3-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl; benzyl, halobenzyl, R G 3 It is hydrogen or (C1-C6)-alkyl.

[0097] S11) Active ingredients of the oxyimino compound class (S11), known as seed dressing compositions, such as "oxabetrinil" ((Z)-1,3-dioxolane-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), known as a seed dressing safener for millet resistant to metolachlor damage, "fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethylone O-(1,3-dioxolane-2-ylmethyl)oxime) (S11-2), known as a seed dressing safener for millet resistant to metolachlor damage, and "cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), known as a seed dressing safener for millet resistant to metolachlor damage.

[0098] S12) refers to active ingredients derived from isothiochromanones, such as methyl acetate [(3-oxo-1H-2-benzothiaran-4(3H)-ylidene)methoxy]acetate (CAS Registry No. 205121-04-6) (S12-1), and related compounds in WO-A-1998 / 13361.

[0099] S13) One or more compounds from group (S13): “Naphthalenedicarboxylic anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed safener for cereals to resist damage from thiocarbamate herbicides; “fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a safener for prochloraz in sown rice; “flurazole” (2-chloro-4-trifluoromethyl-1,3-thiazolyl-5-carboxylate benzyl ester) (S13-3), known as a seed safener for millet to resist damage from metolachlor and isopropylmetolachlor, purchased from American Cyanamid's “CL” 304415 (CAS Registry No. 31541-57-8) (4-Carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4), known as a safer for cereals against imidazolinone damage, purchased from Nitrokemia. MG 191 (CAS Registry No. 96420-72-3) (2-Dichloromethyl-2-methyl-1,3-dioxolane) (S13-5), known as a safer for cereals, purchased from Nitrokemia. 838” (CAS registration number 133993-74-5) (1-oxa-4-azaspiro[4.5]decane-4-dithiocarbamate-2-propenyl ester) (S13-6), “disulfoton” (S-2-ethylthioethyl dithiophosphate O,O-diethyl ester) (S13-7), “dietholate” (O-phenylthiophosphate O,O-diethyl ester) (S13-8), “mephenate” (4-chlorophenyl methylcarbamate) (S13-9).

[0100] S14) contains active ingredients that, in addition to their herbicidal effect on harmful plants, also act as a safener for crops such as rice, for example, "piperazine" or "MY-93" (…). S1-Methyl-1-phenylethylpiperidine-1-thiocarbamate), known as a safener for rice to resist damage from the herbicide glyphosate; "Karifen" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylureuron), known as a safener for rice to resist damage from the herbicide pyrazosulfuron; "Benfluroxyn" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), known as a safener for rice to resist damage from some herbicides; "Methoxyphenone" or "NK 049” (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safe agent for rice to resist damage from some herbicides, and “CSB” (1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Registry No. 54091-06-4) purchased from Kumiai, which is known as a safe agent for rice to resist damage from some herbicides.

[0101] Compounds of formula (S15) or their tautomers, as described in WO-A-2008 / 131861 and WO-A-2008 / 131860, in R H 1 It is (C1-C6)-haloalkyl, and R H 2 It is hydrogen or halogen, and R H 3 R H 4 Each independently is hydrogen, (C1-C) 16 )-alkyl, (C2-C 16 )-Alkenyl or (C2-C 16)-Alkyne, wherein the last three groups are each unsubstituted or substituted by one or more groups selected from: halogen, hydroxyl, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclic, or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkane fused to a 4- to 6-membered saturated or unsaturated carbocyclic ring on one side of the ring. The group is a (C4-C6)-cycloalkenyl group fused to one side of a 4- to 6-membered saturated or unsaturated carbon ring; wherein the last 4 groups are each unsubstituted or substituted by one or more groups selected from: halogen, hydroxyl, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl, and unsubstituted or substituted heterocyclic groups. or R H 3 It is (C1-C4)-alkoxy, (C2-C4)-olefin, (C2-C6)-alkynoxy, or (C2-C4)-haloalkoxy, and R H 4 It is hydrogen or (C1-C4)-alkyl, or R H 3 and R H 4 Together with the directly bonded nitrogen atom, a four- to eight-membered heterocycle is formed, which may contain other cyclic heteroatoms in addition to the nitrogen atom, preferably up to two other cyclic heteroatoms selected from N, O and S, and the heterocycle is unsubstituted or substituted by one or more groups selected from the following: halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio.

[0102] S16) Active ingredients that are mainly used as herbicides but also act as safeners for crops, such as (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoic acid (lactidichlor-ethyl).

[0103] The following examples illustrate the present invention.

[0104] A. Chemical Examples Synthesis of 2-chloro-4-cyclopropyl-3-(S-methylsulfonylimino)-N-(1,3,4-oxadiazol-2-yl)benzamide (Tables Examples 1-4): To a solution of 266.9 mg (0.79 mmol) of 2-chloro-4-cyclopropyl-3-(methylthio)-N-(1,3,4-oxadiazol-2-yl)benzamide in 4 mL of methanol, 123.8 mg (1.58 mmol) of ammonium carbamate was added, followed by the addition of 638.3 mg (1.98 mmol) of iodophenyldiacetic acid in portions. The reaction mixture was stirred at room temperature for 20 hours, and most of the solvent was removed by rotary evaporation. The residue was purified by chromatography to give 106.7 mg (37.1%) of the desired product.

[0105] Synthesis of 2-chloro-4-cyclopropyl-3-(methylthio)-N-(1,3,4-oxadiazol-2-yl)benzamide: To a mixture of 0.50 g (1.82 mmol) of 2-chloro-4-cyclopropyl-3-(methylthio)benzoic acid, 0.17 g (2.00 mmol) of 1,3,4-oxadiazol-2-amine, and 3.0 mL of 3-methylpyridine, 0.30 g (3.64 mmol) of 1-methyl-1H-imidazolium was added dropwise, and the mixture was cooled to 0 °C. At this temperature, 0.35 g (2.91 mmol) of thionyl chloride was added dropwise, and the reaction mixture was slowly heated to room temperature and stirred at this temperature for 24 hours. For post-treatment, a saturated aqueous solution of sodium chloride and dichloromethane were added to separate the organic phase, and the solvent was removed under reduced pressure. The residue was purified by chromatography to give 267 mg (43.6%) of the desired product as a colorless solid.

[0106] Synthesis of 2-methyl-3-(S-methylsulfonylimino)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethyl)-benzamide (Table Examples 1-2): To a solution of 130.0 mg (0.41 mmol) of 2-methyl-3-(methylthio)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethyl)benzamide in 2 mL of methanol, 64.0 mg (0.82 mmol) of ammonium carbamate was added, followed by the addition of 330.0 mg (1.02 mmol) of iodophenyldiacetic acid in portions. The reaction mixture was stirred at room temperature for 20 hours, and most of the solvent was removed by rotary evaporation. The residue was purified by chromatography to give 50.0 mg (33.3%) of the desired product.

[0107] Synthesis of 4-(difluoromethyl)-2-ethyl-3-(S-ethylsulfonylimino)-N-(1,3,4-oxadiazol-2-yl)benzamide (Tables Examples 1-6): To a solution of 185 mg (0.57 mmol) of 4-(difluoromethyl)-2-ethyl-3-(ethylthio)-N-(1,3,4-oxadiazol-2-yl)benzamide in 15 mL of methanol, 88.2 mg (1.13 mmol) of ammonium carbamate was added, followed by the fractional addition of 455 mg (1.41 mmol) of iodophenyldiacetic acid. The reaction mixture was then stirred at room temperature for 20 hours. For post-treatment, a small amount of water was added first, followed by sodium bisulfite. Most of the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and a small amount of water. After phase separation, the solvent in the organic phase was removed by rotary evaporation. The residue was purified by chromatography to give 25.2 mg of pure product.

[0108] Synthesis of 4-(difluoromethyl)-2-ethyl-3-(ethylthio)-N-(1,3,4-oxadiazol-2-yl)benzamide: 634 mg (2.44 mmol) of 4-(difluoromethyl)-2-ethyl-3-(ethylthio)benzoic acid was dissolved in 40 mL of dry tetrahydrofuran and heated to 55-60 °C. Then, 592 mg (3.65 mmol) of 1,1'-carbonyldiimidazole was added in portions. The reaction mixture was stirred under reflux for 3 hours. The mixture was then cooled to room temperature, and 296 mg (1.83 mmol) of 1,1'-carbonyldiimidazole was added in portions. The mixture was then stirred under reflux for another 4 hours. Next, 327 mg (95% purity; 3.65 mmol) of 1,3,4-oxadiazol-2-amine, 10 mL of acetonitrile, and 556 mg (3.65 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added sequentially at room temperature. The mixture in the reaction flask was then stirred at room temperature for three days. To ensure complete reaction, the mixture was stirred at 50°C for five hours, then 164 mg (95% purity; 1.83 mmol) of 1,3,4-oxadiazole-2-amine and 278 mg (1.83 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added. The mixture was stirred at room temperature for another two days. For post-treatment, most of the solvent was removed by rotary evaporation. The residue was treated with deionized water and dichloromethane. After phase separation, the pH of the aqueous phase was adjusted to 3 with dilute hydrochloric acid. The aqueous phase was then extracted with dichloromethane. The organic phases were combined, and the solvent was removed by rotary evaporation. The residue was purified by chromatography to give 505 mg of pure product.

[0109] The examples listed in the table below were prepared using methods similar to those described above, or can be obtained using methods similar to those described above. The compounds listed in the table below are particularly preferred.

[0110] The abbreviations used represent: Me = methyl Et = ethyl c-Pr = cyclopropyl Table 1: Compounds of general formula (I) of the present invention, wherein R', R'' and W are each hydrogen atoms. NMR data of the selected examples: Examples of compounds of the selected general formula (I) 1 H NMR data are reported in two different ways: (a) conventional NMR assessment and interpretation or (b) according to the following methods. 1 In the form of a list of H NMR peaks.

[0111] a) Conventional NMR interpretation Examples 1-10: 1H-NMR (DMSO-D6, δ, ppm): 12.26 (bs, 1H), 9.08 (s, 1H), 7.93 (t, 1H), 7.83-7.79 (m, 2H), 4.89 (s, 1H), 3.42 (s, 3H), 2.63-2.61 (m,1H), 1.03-0.95 (m, 2H), 0.76-0.74 (m, 1H), 0.61-0.58 (m, 1H).

[0112] Examples 1-11: 1 H-NMR (DMSO-D6, δ, ppm): 12.44 (bs, 1H), 9.05 (s, 1H), 7.66 (d, 1H), 7.45 (d, 1H), 4.83 (s, 1H), 3.30 (s, 3H), 2.76 (s, 3H).

[0113] Examples 1-12: 1 H-NMR (DMSO-D6, δ, ppm): 12.23 (bs, 1H), 9.06 (s, 1H), 7.62-7.59 (m, 2H), 4.74 (s, 1H), 3.39 (s, 3H), 2.53-2.50 (m, 1H), 0.97-0.93(m, 2H), 0.66-0.63(m, 1H), 0.57-0.54(m, 1H).

[0114] Examples 1-13: 1 H-NMR (DMSO-D6, δ, ppm): 12.42 (bs, 1H), 9.09 (s, 1H), 7.98 (d, 1H), 7.89 (t, 1H), 7.72 (d, 1H), 3.88 (s, 3H), 3.44 (s, 3H).

[0115] Examples 1-34: 1 HNMR (CDCl3, δ, ppm): 8.17 (bs, 1H), 7.79 (d, 1H), 7.46-7.39 (m, 1H), 3.44 (s, 3H).

[0116] b) NMR peak listing method Selected embodiments 1 H NMR data 1The peaks are recorded in the form of a list of H NMR peaks. For each signal peak, the δ value (in ppm) is listed first, followed by the signal intensity in parentheses. The δ values ​​and signal intensity values ​​of different signal peaks are separated by semicolons.

[0117] For example, the peak list takes the following form: δ 1 (Intensity 1); δ 2 (Intensity 2);……..; δ i (strength i );……; δ n (strength n ) In the printed NMR spectrum of the embodiment, the intensity of a sharp signal is related to its height (in cm), and the true ratio of signal intensity is shown. For a broad signal, multiple peaks or the middle portion of the signal and their relative intensity to the most intense signal in the spectrum can be displayed.

[0118] For calibration 1 For the chemical shifts in the 1H NMR spectra, we use the chemical shifts of tetramethylsilane and / or the solvent, specifically those measured in DMSO. Therefore, a tetramethylsilane peak may appear in the NMR peak list, but it is not guaranteed to appear.

[0119] 1 H NMR peak list and conventional 1 The printed output of H NMR is similar, and therefore usually contains all the peaks listed in a regular NMR interpretation.

[0120] In addition, compared with the conventional 1 Similar to H NMR printouts, they may display solvent signals and signals of stereoisomers of the target compound (which are also provided by this invention) and / or impurity peaks.

[0121] Among the compound signals in the reported solvent and / or water delta range, our 1 The H NMR peak list shows standard solvent peaks, such as the DMSO peak in DMSO-D6 and the water peak, which typically have high average intensities.

[0122] The average intensity of the stereoisomer peaks and / or impurity peaks of the target compound is usually lower than that of the peaks of the target compound (e.g., purity > 90%).

[0123] These stereoisomers and / or impurities may be typical characteristics of a particular preparation method. Therefore, their peaks can help detect the reproducibility of the preparation method, based on "byproduct fingerprints".

[0124] Experts can calculate the peak value of the target compound using known methods (such as MestreC, ACD simulation, and expected values ​​from empirical evaluation), and can optionally use additional intensity filters to separate the peak value of the target compound as needed. This separation method is similar to conventional... 1 The selection of corresponding peaks in H NMR interpretation.

[0125] 1 Further details on the H NMR peak list can be found in Research Disclosure Database Number 564025.

[0126] B. Formulation Examples a) The powdered product is obtained by mixing 10 parts by weight of a compound of formula (I) and / or its salt with 90 parts by weight of talc as an inert substance, and pulverizing the mixture in an impact mill.

[0127] b) A wettable powder that is easily dispersible in water is obtained by mixing 25 parts by weight of the compound of formula (I) and / or its salt, 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 in a pin mill.

[0128] c) A dispersible concentrate readily dispersible in water is obtained by mixing 20 parts by weight of a compound of formula (I) and / or its salt with 6 parts by weight of alkylphenol polyethylene glycol ether (®Triton X 207), 3 parts by weight of isotridecyl polyethylene glycol ether (8 EO) and 71 parts by weight of paraffin mineral oil (boiling range, for example, from about 255°C to greater than 277°C), and grinding it in a friction ball mill to a fineness of less than 5 micrometers.

[0129] d) The emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I) and / or its salt, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.

[0130] e) Water-dispersible granules are obtained through the following methods: 75 parts by weight of the compound of formula (I) and / or its salt, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium dodecyl sulfate, 3 parts by weight of polyvinyl alcohol, and A mixture of 7 parts by weight of kaolin, The mixture is ground in a pin mill and the powder is granulated in a fluidized bed by spraying water, which is applied as a granulation liquid.

[0131] f) Water-dispersible granules are also obtained by the following means: 25 parts by weight of the compound of formula (I) and / or its salt, 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 were homogenized and pre-pulverized in a colloid mill. The mixture was then ground in a bead mill and atomized and dried using a single-phase nozzle in a spray tower.

[0132] C. Biological Examples 1. Post-emergence weed control and crop plant compatibility Seeds of monocotyledonous and dicotyledonous weeds and crops were placed in sandy loam in plastic or wood fiber pots, covered with soil, and cultured in a greenhouse under controlled growing conditions. Two to three weeks after sowing, at the one-leaf stage, the test plants were treated. The compound of the invention, formulated as a wettable powder (WP) or emulsifiable concentrate (EC), was then sprayed onto the green parts of the plants as an aqueous suspension or emulsion, with the addition of 0.5% additive, at a water application rate equivalent to 600 L / ha. After the test plants were kept in the greenhouse under optimal growing conditions for approximately three weeks, the activity of the formulation was visually assessed compared to an untreated control. For example, 100% activity = plant dead, 0% activity = similar to the control plant.

[0133] Tables A1 to A14 below show the efficacy of selected compounds of general formula (I) according to Table 1 against a variety of harmful plants at application rates of 80 g / ha or less. These results were obtained using the experimental methods described above. Appendices “a”, “b”, and “c” are distinguished based on the dosage used when all other aspects of the tested harmful plants are identical.

[0134] Table A1a: Post-emergence efficacy of ALOMY at 20 g / ha, expressed as a percentage. Table A1b: Post-emergence efficacy of ALOMY at 80 g / ha, expressed as a percentage. Table A2a: Post-emergence efficacy of AMARE at 5 g / ha, expressed as a percentage. Table A2b: Post-emergence efficacy of AMARE at 20 g / ha, expressed as a percentage. Table A2c: Post-emergence efficacy of AMARE at 80 g / ha, expressed as a percentage. Table A3a: Post-emergence efficacy of AVEFA at 20 g / ha, expressed as a percentage. Table A3b: Post-emergence efficacy of AVEFA at 80 g / ha, expressed as a percentage. Table A4a: Post-emergence efficacy of DIGSA at 5 g / ha, expressed as a percentage. Table A4b: Post-emergence efficacy of DIGSA at 20 g / ha, expressed as a percentage. Table A4c: Post-emergence efficacy of DIGSA at 80 g / ha, expressed as a percentage. Table A5a: Postemergence efficacy of ECHCG at 5 g / ha, expressed as a percentage. Table A5b: Postemergence efficacy of ECHCG at 20 g / ha, expressed as a percentage. Table A5c: Postemergence efficacy of ECHCG at 80 g / ha, expressed as a percentage. Table A6a: Post-emergence efficacy of LOLRI at 20 g / ha, expressed as a percentage. Table A6b: Post-emergence efficacy of LOLRI at 80 g / ha, expressed as a percentage. Table A7a: Post-emergence efficacy of MATIN at 5 g / ha, expressed as a percentage. Table A7b: Post-emergence efficacy of MATIN at 20 g / ha, expressed as a percentage. Table A7c: Post-emergence efficacy of MATIN at 80 g / ha, expressed as a percentage. Table A8a: Post-emergence efficacy of PHBPU at 5 g / ha, expressed as a percentage. Table A8b: Post-emergence efficacy of PHBPU at 20 g / ha, expressed as a percentage. Table A8c: Post-emergence efficacy of PHBPU at 80 g / ha, expressed as a percentage. Table A9a: Post-emergence efficacy of POLCO at 80 g / ha, expressed as a percentage. Table A10a: Post-emergence efficacy of SETVI at 5 g / ha, expressed as a percentage. Table A10b: Post-emergence efficacy of SETVI at 20 g / ha, expressed as a percentage. Table A10c: Post-emergence efficacy of SETVI at 80 g / ha, expressed as a percentage. Table A11a: Post-emergence efficacy of VERPE at 5 g / ha, expressed as a percentage. Table A11b: Post-emergence efficacy of VERPE at 20 g / ha, expressed as a percentage. Table A11c: Efficacy of VERPE at 80 g / ha after emergence, expressed as a percentage. Table A12a: Post-emergence efficacy of VIOTR at 5 g / ha, expressed as a percentage. Table A12b: Post-emergence efficacy of VIOTR at 20 g / ha, expressed as a percentage. Table A12c: Post-emergence efficacy of VIOTR at 80 g / ha, expressed as a percentage. Table A13a: Post-emergence efficacy of ABUTH at 5 g / ha, expressed as a percentage. Table A13b: Post-emergence efficacy of ABUTH at 20 g / ha, expressed as a percentage. Table A13c: Post-emergence efficacy of ABUTH at 80 g / ha, expressed as a percentage. Table A14a: Post-emergence efficacy of KCHSC at 20 g / ha, expressed as a percentage. Table A14b: Post-emergence efficacy of KCHSC at 80 g / ha, expressed as a percentage.

[0135] Tables A15 to A19 below show the compatibility of selected compounds of general formula (I) according to Table 1 with plant crops at application rates of 20 g / ha or less. These results were observed in experiments conducted according to the experimental methods described above. The tables report the observed efficacy (in percentage) in the selected plant crops compared to the untreated control. Appendices “a”, “b”, and “c” are distinguished based on the dosage used when all other aspects of the tested plant crops are identical.

[0136] Table A15a: Post-emergence efficacy of ZEAMX at 5 g / ha, expressed as a percentage. Table A15b: Post-emergence efficacy of ZEAMX at 20 g / ha, expressed as a percentage. Table A16a: Post-emergence efficacy of TRZAS at 5 g / ha, expressed as a percentage. Table A16b: Post-emergence efficacy of TRZAS at 20 g / ha, expressed as a percentage. Table A17a: Post-emergence efficacy of ORYSA at 5 g / ha, expressed as a percentage. Table A17b: Post-emergence efficacy of ORYSA at 20 g / ha, expressed as a percentage. Table A18a: Post-emergence efficacy of GLXMA at 5 g / ha, expressed as a percentage. Table A18b: Post-emergence efficacy of GLXMA at 20 g / ha, expressed as a percentage. Table A19a: Post-emergence efficacy of BRSNW at 5 g / ha, expressed as a percentage. Table A19b: Post-emergence efficacy of BRSNW at 20 g / ha, expressed as a percentage.

[0137] The results showed that, under post-emergence treatment, the compounds of general formula (I) of the present invention exhibited good herbicidal efficacy against harmful plants such as: Abutilon theophrasti, Alopecurus aloess, Amaranth retroflexus, Avefa, Digitaria sanguinalis, Ecclesia lingua, Kochia scoparia, Lorraine serrata, Matricaria champaca, Phoebe bournei, Polygonum aviculare, Setvi, Veronica persica, and Viola tricolor, and good crop compatibility with crops such as: Rice, Maize, Brassica napus, Soybean, and Wheat, at an application rate of 0.02 kg per hectare or less.

[0138] 2. Pre-emergence weed control and crop-plant compatibility Seeds of monocotyledonous and dicotyledonous weeds and crops were placed in plastic pots or organic planting pots and covered with soil. The compound of the invention, formulated as a wettable powder (WP) or emulsifiable concentrate (EC), was then applied to the surface of the soil as an aqueous suspension or emulsion, with the addition of 0.5% additive, at a water application rate equivalent to 600 l / ha. After treatment, the pots were kept at room temperature and under conditions favorable to the growth of the test plants. After approximately 3 weeks, the efficacy of the formulation was visually assessed as a percentage, compared to an untreated control. For example, 100% activity = plants had died, 0% activity = similar to control plants.

[0139] Tables B1 to B14 below show the efficacy of selected compounds of general formula (I) according to Table 1 against a variety of harmful plants at application rates of 80 g / ha or less. These results were obtained using the experimental methods described above. Appendices “a”, “b”, and “c” are distinguished based on the dosage used when all other aspects of the harmful plants tested are identical.

[0140] Table B1a: Pre-emergence efficacy of ALOMY at 80 g / ha, expressed as a percentage. Table B2a: Pre-emergence efficacy of AMARE at 20 g / ha, expressed as a percentage. Table B2b: Pre-emergence efficacy of AMARE at 80 g / ha, expressed as a percentage. Table B3a: Pre-emergence efficacy of AVEFA at 20 g / ha, expressed as a percentage. Table B3b: Pre-emergence efficacy of AVEFA at 80 g / ha, expressed as a percentage. Table B4a: Pre-emergence efficacy of DIGSA at 20 g / ha, expressed as a percentage. Table B4b: Pre-emergence efficacy of DIGSA at 80 g / ha, expressed as a percentage. Table B5a: Pre-emergence efficacy of ECHCG at 20 g / ha, expressed as a percentage. Table B5b: Pre-emergence efficacy of ECHCG at 80 g / ha, expressed as a percentage. Table B6a: Pre-emergence efficacy of LOLRI at 80 g / ha, expressed as a percentage. Table B7a: Pre-emergence efficacy of MATIN at 20 g / ha, expressed as a percentage. Table B7b: Pre-emergence efficacy of MATIN at 80 g / ha, in % Table B8a: Pre-emergence efficacy of PHBPU at 20 g / ha, expressed as a percentage. Table B8b: Pre-emergence efficacy of PHBPU at 80 g / ha, expressed as a percentage. Table B9a: Pre-emergence efficacy of POLCO at 20 g / ha, expressed as a percentage. Table B9b: Pre-emergence efficacy of POLCO at 80 g / ha, expressed as a percentage. Table B10a: Pre-emergence efficacy of SETVI at 20 g / ha, expressed as a percentage. Table B10b: Pre-emergence efficacy of SETVI at 80 g / ha, expressed as a percentage. Table B11a: Pre-emergence efficacy of VERPE at 20 g / ha, expressed as a percentage. Table B11b: Pre-emergence efficacy of VERPE at 80 g / ha, expressed as a percentage. Table B12a: Pre-emergence efficacy of VIOTR at 20 g / ha, expressed as a percentage. Table B12b: Pre-emergence efficacy of VIOTR at 80 g / ha, expressed as a percentage. Table B13a: Pre-emergence efficacy of ABUTH at 20 g / ha, expressed as a percentage. Table B13b: Pre-emergence efficacy of ABUTH at 80 g / ha, in % Table B14a: Pre-emergence efficacy of KCHSC at 20 g / ha, expressed as % Table B14b: Pre-emergence efficacy of KCHSC at 80 g / ha, in %

[0141] Tables B15 to B19 below show the compatibility of selected compounds of general formula (I) according to Table 1 with plant crops at application rates of 80 g / ha or less. These results were observed in trials conducted according to the experimental methods described above. The tables report the observed efficacy (in percentage) in the selected plant crops compared to the untreated control. Appendices “a”, “b”, and “c” are distinguished based on the dosage used when all other aspects of the tested plant crops are identical.

[0142] Table B15a: Pre-emergence efficacy of ZEAMX at 20 g / ha, expressed as a percentage. Table B15b: Pre-emergence efficacy of ZEAMX at 80 g / ha, expressed as a percentage. Table B16a: Pre-emergence efficacy of TRZAS at 20 g / ha, expressed as a percentage. Table B16b: Pre-emergence efficacy of TRZAS at 80 / ha, in % Table B17a: Pre-emergence efficacy of ORYSA at 20 g / ha, expressed as a percentage. Table B18a: Pre-emergence efficacy of GLXMA at 20 g / ha, expressed as a percentage. Table B18b: Pre-emergence efficacy of GLXMA at 80 g / ha, expressed as a percentage. Table B19a: Pre-emergence efficacy of BRSNW at 20 g / ha, expressed as a percentage. Table B19b: Pre-emergence efficacy of BRSNW at 80 g / ha, expressed as a percentage.

[0143] The results showed that, under pre-emergence treatment, the compounds of general formula (I) of the present invention exhibited good herbicidal efficacy against harmful plants such as: Abutilon theophrasti, Alopecurus alomygdalinus, Amaranth purpurea, Avefa, Digitaria sanguinalis, Ecclesia argyi, Kochia scoparia, Lorraine serrata, Matricaria champaca, Phoebe bournei, Polygonum aviculare, Setvi, Veronica persica, and Viola tricolor, and good crop compatibility with crops such as: Rice, Maize, Brassica napus, Soybean, and Wheat, at an application rate of 0.08 kg per hectare or less.

[0144] 3. Comparison of the herbicidal efficacy and crop compatibility of the compounds of the present invention with those of known compounds from WO2013 / 124228 that have similar structures before and after emergence.

[0145] Table C1 below compares the compounds of the present invention with structurally similar compounds from known literature, WO2013 / 124228. The compounds of the present invention differ from those known in the literature in a key structural feature. Unlike the compounds known in the literature, the oxadiazole rings of the compounds of the present invention (1-1, 1-2, 1-7, 1-11, 1-13) do not contain any methyl substituents.

[0146] Table C1

[0147] Tables C2-C11 below show the post-emergence efficacy of the compounds of the present invention and structurally similar compounds from known literature WO2013 / 124228 against various harmful plants at an application rate of 20 g / ha or less. These results were obtained by the experimental methods described above.

[0148] Table C2 Table C3 Table C4 Table C5 Table C6 Table C7 Table C8 Table C9 Table C10 Table C11

[0149] The results shown in Tables C2 to C11 demonstrate that, compared with compounds 7-18, 7-6, 7-17, and 7-12 known from the literature (WO2013 / 124228) that are structurally similar, the compounds of the present invention (1-1, 1-2, 1-7, 1-11) at an application rate of 20 g or less of active substance per hectare have significantly improved post-emergence weed control efficacy against harmful plants such as: Abutilon theophrasti, Amaranth retroflexus, Avefa, Digitaria sanguinalis, Ecclesia lataniae, Matin, Phoebe bournei, Setvi, Verpe, and Viola tricolor.

[0150] Tables C12-C16 below show the post-emergence plant crop compatibility of the compounds of the present invention and structurally similar compounds from known literature WO2013 / 124228, at an application rate of 20 g / ha or less. These results were obtained by the experimental methods described above.

[0151] Table C12 Table C13 Table C14 Table C15 Table C16

[0152] The results shown in Tables C12 to C16 indicate that the compounds of the present invention (1-7, 1-13) at an application rate of 20 g per hectare or less have significantly improved post-emergence compatibility with the following crops, compared with compounds 7-17 and 7-29 known from the literature (WO2013 / 124228) that are structurally similar: rapeseed (BRSNW), soybean (GLXMA), rice (ORYSA), wheat (TRZAS), and maize (ZEAMX).

[0153] Tables C17-C28 below show the pre-emergence efficacy of the compounds of the present invention and structurally similar compounds from known literature WO2013 / 124228 against various harmful plants at an application rate of 80 g / ha or less. These results were obtained by the experimental methods described above.

[0154] Table C17 Table C18 Table C19 Table C20 Table C21 Table C22 Table C23 Table C24 Table C25 Table C26 Table C27 Table C28

[0155] The results shown in Tables C17 to C28 demonstrate that, compared with compounds 7-18, 7-6, 7-17, and 7-12 known from the literature (WO2013 / 124228) that are structurally similar, the compounds of the present invention (1-1, 1-2, 1-7, 1-11) at an application rate of 80 g or less of active substance per hectare have significantly improved pre-emergence weed control efficacy against harmful plants such as: Abutilon theophrasti, Alomy, Amaranth retroflexus, Avefa, Digitaria sanguinalis, Ecclesia lataniae, Matin, Phoebe bournei, Setvi, Verpe, and Viola tricolor.

[0156] Tables C29-C32 below show the pre-emergence plant crop compatibility of the compounds of the present invention and structurally similar compounds from known literature WO2013 / 124228, at an application rate of 20 g / ha or less. These results were obtained by the experimental methods described above.

[0157] Table C29 Table C30 Table C31 Table C32

[0158] The results shown in Tables C29 to C32 indicate that the compounds of the present invention (1-7, 1-13) at an application rate of 80 g per hectare or less have significantly improved pre-emergence compatibility with the following crops, compared with compounds 7-17 and 7-29 known from the literature (WO2013 / 124228) that are structurally similar: rapeseed (BRSNW), soybean (GLXMA), rice (ORYSA), and maize (ZEAMX).

Claims

1. A sulfonyliminobenzamide of formula (I) or a salt thereof wherein The symbols are defined as follows: X is a halogen, cyano, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkylthio, halogen-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, or (C3-C6)-cycloalkyl. Z represents halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-ynyl, halo-(C3-C6)-ynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, halo-(C1-C6)-alkoxy, (C1-C6)-alkylsulfonyl. W represents hydrogen or halogen. R is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, or (C1-C6)-alkoxy-(C1-C6)-alkyl. R' is hydrogen, cyano, or (C1-C6)-alkyl. R'' represents hydrogen or (C1-C6)-alkyl carbonyl.

2. The sulfonylimide-based benzamide according to claim 1, wherein... X is a halogen, (C1-C3)-alkyl, (C1-C3)-alkoxy, or (C3-C6)-cycloalkyl. Z represents halogen, (C1-C3)-alkyl, halogen-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, or halogen-(C1-C3)-alkoxy. W represents hydrogen or fluorine. R is (C1-C3)-alkyl. R' is hydrogen. R'' represents hydrogen.

3. The sulfonylimide-based benzamide according to claim 1, wherein... X can be chloro, methyl, ethyl, methoxy, or cyclopropyl. Z represents chloro, methyl, difluoromethyl, trifluoromethyl, cyclopropyl, or trifluoromethoxy. W represents hydrogen. R represents methyl or ethyl. R' is hydrogen. R'' represents hydrogen.

4. A herbicidal composition comprising at least one sulfonyliminobenzamide as described in any one of claims 1 to 3, and mixed with a formulation adjuvant.

5. The herbicidal composition according to claim 4, comprising at least one other pesticide-active substance selected from: insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.

6. A method for controlling unwanted plants, characterized in that, Apply an effective amount of at least one sulfonylimide benzamide according to any one of claims 1 to 3 or the herbicidal composition according to claim 4 or 5 to the plant or the location of unwanted plants.

7. Use of the sulfonylimide benzamide of formula (I) according to any one of claims 1 to 3 or the herbicidal composition according to claim 4 or 5 for the control of unwanted plants.

8. Use according to claim 7, characterized in that, The sulfonylimide benzamide of formula (I) is used to control unwanted plants in beneficial plant crops.

9. Use according to claim 8, characterized in that, The useful plants mentioned are genetically modified useful plants.

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