Sulfonimidoyl benzamide having herbicidal activity

Abstract

The present invention relates to sulfonimidoylbenzamide of formula (I) as a herbicide. In chemical formula (I), X, W, Z, R, R' and R'' represent radicals such as alkyl, cycloalkyl, haloalkyl and halogen radicals.

Description

Technology Field

[0001] The present invention relates to the technical field of herbicides, particularly to the technical field of herbicides for selectively controlling broadleaf weeds and weedy grass weeds in plant crops. Background Technology

[0002] WO 2011 / 035874 A1 discloses N-(1,2,5-oxadiazole-3-yl)benzamide having herbicidal activity. European patent application EP10174893, which has an earlier priority date but was not disclosed prior to the priority date of the present application, discloses specific N-(tetrazole-5-yl)- and N-(triazole-5-yl)benzamides and -nicotinamide as herbicides. Herbicidal 3-sulfinimidoylbenzamide and 3-sulfonimidoylbenzamide are known from WO 2013 / 124228. However, the herbicidal activity and / or crop suitability of the compounds specified in these documents are not always sufficient. The problem to be solved

[0003] The objective of the present invention was to provide a herbicidal active compound having properties improved over those of the compounds disclosed in the prior art. means of solving the problem

[0004] Now, it has been found that certain sulfonimidoylbenzamides having an unsubstituted 1,3,4-oxadiazole on the amide nitrogen are particularly suitable as herbicides. Accordingly, the present invention provides a sulfonimidoylbenzamide of formula (I) or a salt thereof:

[0005]

[0006] In the above equation, the symbol is defined as follows:

[0007] 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, (C3-C6)-cycloalkyl, and

[0008] Z is a halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, halo-(C1-C6)-alkoxy, (C1-C6)-alkylsulfonyl, and

[0009] W is hydrogen, a halogen, and,

[0010] R is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, and

[0011] R' is hydrogen, cyano, (C1-C6)-alkyl, and

[0012] R'' is hydrogen, (C1-C6)-alkyl carbonyl.

[0013] In formula (I) and all formulas below, alkyl radicals having more than two carbon atoms may be straight-chain or branched-chain. Alkyl radicals are, for example, methyl, ethyl, n-propyl or isopropyl, n-, iso-, t- or 2-butyl, pentyl, and hexyls such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. In a similar manner, alkenyls mean, 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. Alkynyl means, for example, propargyl, but-2-in-1-yl, but-3-in-1-yl, and 1-methylbut-3-in-1-yl. Multiple bonds may be at any position in each unsaturated radical. Cycloalkyl means a carbocyclic saturated ring system having 3 to 6 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0014] "Haloalkyl," "haloalkenyl," and "haloalkynyl" each mean alkyl, alkenyl, and alkynyl that are partially or completely substituted by the same or different halogen atoms, e.g., monohaloalkyl, e.g., CH2CH2Cl, CH2CH2Br, CHClCH3, CH2Cl, CH2F; dihaloalkyl, e.g., CH2CHF2, CH2CHCl2, CH2CHBr2, CF2CH3, CHCl2, CHF2; perhaloalkyl, e.g., CCl3, CFCl2, CClF2, CF3, CF2CClF2, CF2CClFCF3; polyhaloalkyl, e.g., CH2CHFCl, CF2CClFH, CF2CBrFH, CH2CF3. Here, the term perhaloalkyl also includes the term perfluoroalkyl.

[0015] "Alkoxy" refers to an alkyl radical attached via an oxygen atom, and includes, for example (but not limited to) 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, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, It is a (C1-C6)-alkoxy such as 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy.

[0016] "Alkoxyalkyl" refers to an alkoxy radical attached through an alkyl group.

[0017] "Haloalkoxy" means a haloalkyl radical attached through an oxygen atom, such as (but not limited to) OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl.

[0018] According to the present invention, "alkylthio" represents a straight-chain or branched-chain S-alkyl, 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-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, (C1-C6)-alkylthios such as 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

[0019] According to the present invention, unless otherwise defined, "alkyl carbonyl (alkyl-C(=O)-)" represents an alkyl radical attached to a backbone via -C(=O)-, such as (C1-C6)-alkyl carbonyl. The number of carbon atoms relates to the alkyl radical in the alkyl carbonyl group.

[0020] The term "halogen" means, for example, fluorine, chlorine, bromine, or iodine. When the above term is used for radicals, "halogen" means, for example, fluorine, chlorine, bromine, or iodine atoms.

[0021] Where a compound can form a tautomer through hydrogen transfer, the structure of which may not be formally included in Formula (I), such tautomer is nevertheless included in the definition of the compound of the present invention of Formula (I), unless a specific tautomer is being considered. For example, many carbonyl compounds may exist in both keto and enol forms, and both forms are included in the definition of the compound of Formula (I).

[0022] Compounds of general formula (I) may exist as stereoisomers depending on the nature of the substituents and the manner in which the substituents are attached. For example, if one or more asymmetrically substituent carbon atoms are present, enantiomers and diastereomers may occur. Additionally, the sulfur atom of the sulfoxymino group exists as a chiral center. Stereoisomers can be obtained from a mixture obtained from preparation by conventional separation methods, such as a chromatographic separation process. Similarly, stereoisomers can be selectively prepared using stereoselective reactions utilizing optically active starting materials and / or auxiliaries. The present invention also relates to all stereoisomers included in general formula (I) but not specifically defined, and mixtures thereof. The present invention also relates to all E / Z isomers included in general formula (I) but not specifically defined, and mixtures thereof.

[0023] Compounds of formula (I) can form salts. Salts can be formed by the action of a base on a compound of formula (I) that possesses 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, and hydroxides, carbonates, and hydrogen carbonates of ammonium, alkali metal, or alkaline earth metals, in particular sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate. These salts are compounds in which acidic hydrogen is substituted with an agriculturally suitable cation, e.g., a metal salt, particularly an alkali metal salt or an alkaline earth metal salt, particularly a sodium and potassium salt, or an ammonium salt, a salt with an organic amine, or a quaternary ammonium salt, e.g., R, R*, R**, and R***, each independently substituted with an organic radical, particularly an alkyl, aryl, aralkyl, or alkylaryl cation of the formula [NRR*R**R***]+. Alkylsulfonium and alkylsulfonium salts, such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfonium salts, are also useful.

[0024] The compound of formula (I) can form a salt by adding a suitable inorganic or organic acid, such as an inorganic acid like HCl, HBr, H2SO4, H3PO4, or HNO3, or a carboxylic acid like formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or a sulfonic acid like p-toluenesulfonic acid, to a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino, or pyridino. Such a salt contains the conjugate base of the acid as an anion.

[0025] Preferably, in a compound of general formula (I)

[0026] X is a halogen, (C1-C3)-alkyl, (C1-C3)-alkoxy, (C3-C6)-cycloalkyl, and

[0027] Z is a halogen, (C1-C3)-alkyl, halogen-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, halo-(C1-C3)-alkoxy, and

[0028] W is hydrogen, fluorine, and

[0029] R It is (C1-C3)-alkyl, and

[0030] R' is hydrogen, and

[0031] R'' is hydrogen.

[0032] Particularly preferably, in a compound of general formula (I)

[0033] X is chlorine, methyl, ethyl, methoxy, cyclopropyl, and

[0034] Z is chlorine, methyl, difluoromethyl, trifluoromethyl, cyclopropyl, trifluoromethoxy, and

[0035] W is hydrogen, and

[0036] R It is methyl and ethyl, and

[0037] R' is hydrogen, and

[0038] R'' is hydrogen.

[0039] The compound of the present invention can be prepared according to the method described in WO 2013 / 124228.

[0040] Accordingly, the compound of the present invention can be prepared stepwise, for example, by base-catalyzing benzoyl chloride (II) with 2-amino-1,3,4-oxadiazole (VII) according to the method shown in Reaction Scheme 1, starting with a thioether step of formula (I-thioether). Subsequently, the thioether intermediate can be converted to the sulfonimidoylbenzamide of the present invention of formula (I) according to Reaction Scheme 4.

[0041]

[0042] The compound of the present invention can likewise be prepared stepwise in the first step of the thioether of formula (I-thioether) by reacting the benzoic acid of formula (IV) with 2-amino-1,3,4-oxadiazole (VII) according to the method shown in Reaction Scheme 2. Subsequently, the thioether intermediate can be converted to the sulfonimidoylbenzamide of formula (I) of the present invention according to Reaction Scheme 4.

[0043]

[0044] For activation, dehydration reagents commonly used in amidation reactions, such as 1,1'-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinan 2,4,6-trioxide (T3P), may be used.

[0045] Compounds of the present invention in which the substituent R'' is not hydrogen can be prepared by reacting N-(1,3,4-oxadiazole-2-yl)-arylcarboxamide (I-NH) with a compound of general formula (VIII) according to the method shown in Reaction Scheme 3, for example, where L is a leaving group, for example, chlorine, bromine, iodine, mesiloxy, tosiloxy, trifluorosulfonyloxy, etc.:

[0046]

[0047] The compound of formula (VIII) can be commercially available or prepared by known methods described in the literature.

[0048] The compound of the present invention of formula (I) can be prepared, for example, from a thioether of the corresponding formula (I-thioether) (Reaction Scheme 4). To this end, the thioether is converted to the corresponding sulfilimin using, for example, cyanamide and an oxidizing agent (iodosobenzene diacetate, sodium hypochlorite, or N-bromosuccinimide), which can be further oxidized to sulfoxymin. Examples of oxidizing agents suitable for oxidation to sulfoxymin are a mixture of meta-chloroperbenzoic acid, sodium permanganate or sodium periodate, and ruthenium trichloride. NH-sulfoxymin can be obtained, for example, from sulfoxide using sodium azide and sulfuric acid, and can be functionalized at the nitrogen atom using reagents such as cyanogen bromide, acid chloride or acid anhydride, chloroformic acid ester, nitric acid, or other compounds. N-sulfonated sulfilimines can be oxidized to the corresponding sulfoximines using, for example, hydrogen peroxide. Alternatively, sulfoxides can be reacted to form N-acylated or N-sulfonated sulfoximines. Subsequently, carboxamides or sulfonamides can be cleaved to NH-sulfoximines. Such synthetic methods for generating sulfilimines and sulfoximines from thioethers, generating sulfoximines from sulfoxides, or derivatizing sulfilimines and sulfoximines containing NH-sulfoximines are, for example, 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; It is described in WO 2007 / 095229, WO 2008 / 141843, US 2008 / 0207910, US 2008 / 0194634 and US 2010 / 0056534.

[0049]

[0050] If necessary, a protecting group must be used in these synthetic sequences to achieve sufficient selectivity. In particular, functionalization at NH-sulfoxymin competes in principle with similar functionalization at the amide nitrogen atom.

[0051] It may be advantageous to change the order of the reaction steps. For example, benzoic acid containing a sulfoxide cannot be easily converted to its acid chloride. One option here is to first produce an amide in the thioether step and then oxidize the thioether to a sulfoxide. Since sulfoxymin, particularly sulfylimine, is not sufficiently stable under some conditions (Bolm, C. Adv. Synth. Catal. 2010, 352, 309), it may be advantageous to first synthesize a benzamide in the thioether step and then produce a sulfylimine or sulfoxyminine from the thioether at the end of the synthesis sequence, as shown in the reaction scheme above. However, where stability is sufficient, depending on the substitution pattern, it may also be useful to first produce a sulfylimine or sulfoxyminine from the thioether in the benzoic acid step (or a much earlier step) and then convert the benzoic acid to its amide.

[0052] Instead of free benzoic acid, it may be advantageous to use its derivatives for the reaction. Sometimes, for the stability of the functional group, it is sufficient to move in either an acidic or a basic medium; that is, working with only free benzoic acid or only its salt. In many cases, esters such as methyl or ethyl esters are suitable. Tert-butyl esters often sterically and effectively shield the carboxyl group against nucleophilic reagents and are easily cleaved in acidic media (TW Greene, PGM Wuts, Protective Groups in Organic Synthesis, 2nd ed., John Wiley & Sons, Inc. 1991, p. 227 ff.). Residues that are much more stable than the carboxyl group but can be easily obtained from carboxylic acids and easily converted back to free carboxylic acids are also suitable. These residues include, for example, oxazoline (TW Greene, PGM Wuts, Protective Groups in Organic Synthesis, 2nd ed., John Wiley & Sons, Inc. 1991, p. 265 ff.; Z. Hell et al, Tetrahedron Letters 43 (2002), 3985-3987).

[0053] In addition, it is also possible to obtain the NH-sulfoxymin of the present invention of formula (I) in one step from a thioether of the corresponding formula (I-thioether) (Reaction Scheme 5). To this end, the thioether is directly converted to the corresponding NH-sulfoxymin using, for example, ammonium carbamate and iodosobenzene diacetate (JA Bull et al. Synlett 2017, 28, 2525-2538).

[0054]

[0055] In the synthesis method mentioned above, the sulfoxymin of the present invention of formula (I) is obtained as a racemic mixture. A pure enantiomer can be obtained therefrom by chiral separation methods known to those skilled in the art, for example, by chromatographic separation of the enantiomer on a chiral support material.

[0056] Post-treatment of each reaction mixture is carried out by generally known processes, e.g., crystallization, aqueous extraction, chromatography, or a combination of these methods.

[0057] A set of compounds of formula (I) and / or salts thereof that can be synthesized by the aforementioned reaction may also be prepared in a parallelized manner, which may be carried out manually, partially automatically, or fully automatically. For example, it is possible to automate the execution of the reaction, the post-processing or purification of the products and / or intermediates. Overall, this is, for example, D. Tiebes' Combinatorial Chemistry - Synthesis, Analysis, Screening (Editor: G It is understood to mean the procedure described in Wiley, 1999, pp. 1 to 34 (Wiley, Nther Jung).

[0058] For parallel execution of reaction and post-processing, various commercially available equipment may be used, for example, the Calypso reaction block of Barnstead International, Dubuque, Iowa 52004-0797, USA, or the reaction station of Radleys, Shirehill, Saffron Walden, Essex, CB11 3AZ, England, or the MultiPROBE automated workstation of Perkin Elmer, Waltham, Massachusetts 02451, USA. Available equipment for parallel purification of the compound of general formula (I) and its salt, or intermediates generated during the manufacturing process, includes chromatography equipment, for example, the equipment of ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

[0059] The listed devices result in a modular procedure where individual work steps are automated but manual operations must be performed between work steps. This can be bypassed by using a partially integrated or fully integrated automation system where each automation module is operated, for example, by a robot. Such automation systems are available, for example, from Caliper, Hopkinton, MA 01748, USA.

[0060] The performance of individual or multiple synthesis steps can be supported by using polymer-supported reagents / scavenger resins. Expert literature describes a series of experimental protocols, for example, ChemFiles, vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

[0061] In addition to the methods described herein, compounds of general formula (I) and their salts may be prepared wholly or partially by solid-phase support methods. To this end, individual intermediates or all intermediates during synthesis, or intermediates during synthesis adapted to the relevant procedure, are bonded to a synthetic resin. Solid-phase support synthesis methods are described in the technical literature, for example, Barry A. Bunin's "The Combinatorial Index", Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (Editor: G This is sufficiently described in (Jung), Wiley, 1999. The use of solid-phase supported synthesis methods enables numerous protocols known from the literature, which can be performed manually or automatically. Reactions can be carried out, for example, using IRORI technology in a microreactor at Nexus Biosystems, 12140 Community Road, Poway, CA 92064, USA.

[0062] In both solid and liquid phases, the performance of individual or multiple synthesis steps can be supported by the use of microwave technology. Numerous experimental protocols are described in the literature, for example, Microwaves in Organic and Medicinal Chemistry (Editors: CO Kappe and A. Stadler), Wiley, 2005.

[0063] The manufacture by the process described herein provides a compound of formula (I) and a salt thereof in the form of a material set known as a library. The present invention also provides a library comprising at least two types of a compound of formula (I) and a salt thereof.

[0064] The compound of the present invention of formula (I) (and / or salt thereof) (hereinafter collectively referred to as “compound of the present invention”) has excellent herbicidal efficacy against a wide range of economically important monocotyledonous and dicotyledonous annual pest plants. The active ingredient also has good control efficacy against perennial pest plants that are difficult to control and produce new shoots from rhizomes, rootstocks, or other perennial organs.

[0065] Accordingly, the present invention also provides a method for controlling unwanted plants or controlling the growth of plants, preferably plant crops, wherein one or more compounds of the present invention are applied to a plant (e.g., a harmful plant such as a monocotyledonous or dicotyledonous weed or an unwanted crop plant), a seed (e.g., a vegetative propagator such as a grain, seed, tuber, or budded stem part), or an area where the plant is growing (e.g., a cultivation site). The compounds of the present invention may be used, for example, before sowing (or by incorporation into the soil if appropriate), before or after germination. Some representative embodiments of monocotyledonous and dicotyledonous weed groups that can be controlled by the compounds of the present invention are presented below, but the listing does not imply limitation to specific species.

[0066] Monocotyledonous harmful plants of the following genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Iscaemum (Ischaemum), Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0067] Dicotyledonous weeds of the following genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Gallium, Hibiscus (Hibiscus), Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Soncus (Sonchus), Sphenoclea, Stellaria, Taraxacum, Thlaspi, Tripolium,Urtica, Veronica, Viola, Xanthium.,

[0068] When the compound of the present invention is applied to the soil surface before germination, the emergence of weed seedlings is completely prevented, or weeds grow until they reach the cotyledon stage, after which growth stops and they eventually die completely after 3 to 4 weeks.

[0069] When the active ingredient is applied to the green parts of plants by the post-budding method, growth ceases after treatment, and harmful plants remain at the growth stage at the time of application or die completely after a certain period; as a result, competition with weeds harmful to crop plants is continuously eliminated at a very early stage.

[0070] The compound of the present invention has excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, but is not effective against economically important crop plants, e.g., dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or Allium, Ananas, Asparagus, Avena, Hordeum Monocotyledonous crops of the genera Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, and Zea suffer little to no damage depending on the structure of the specific compound of the present invention and the dosage thereof. For this reason, the present compound is highly suitable for the selective control of unwanted plant growth in plant crops, such as agriculturally useful plants or ornamental plants.

[0071] Furthermore, the compounds of the present invention (depending on their specific structure and applied dosage) possess excellent growth-regulating properties in crop plants. Since they act as regulators to the metabolism of the plant itself, they can be used, for example, to induce drying and growth retardation to exert a controlled effect on plant components and facilitate harvesting. Additionally, they are suitable for generally controlling and inhibiting unwanted vegetative growth without causing the plant to die. Inhibition of vegetative growth plays an important role in many monocot and dicot crops, for example, as it can reduce or completely prevent lodging.

[0072] Due to their herbicidal properties and regulatory effects on plant growth, active ingredients can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. Transgenic plants generally feature specific advantageous traits, such as resistance to specific pesticides, particularly herbicides, and resistance to plant diseases or disease-causing organisms, such as specific insects or microorganisms like fungi, bacteria, or viruses. Other specific traits relate to, for example, the yield, quality, storability, composition, and specific components of the harvest. For instance, transgenic plants with increased starch content or altered starch quality, or those with different fatty acid compositions of the harvest, are known.

[0073] In relation to transgenic crops, the compounds of the present invention are preferably used in economically important transgenic crops of useful and ornamental plants, such as cereals like wheat, barley, rye, oats, millet, rice, and corn, as well as crops of sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other vegetables. The compounds of the present invention can be preferably used as herbicides in crops of useful plants that are resistant to the phytotoxic effects of herbicides or have been genetically engineered to be resistant.

[0074] Conventional methods for producing novel plants with modified characteristics compared to existing plants consist, for example, of traditional cultivation methods and the generation of mutants. Alternatively, novel plants with modified characteristics may be produced using genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). For example, in many cases, the following is described:

[0075] - Genetic modification of crop plants intended to modify starch synthesized in plants (e.g., WO 92 / 11376, WO 92 / 14827, WO 91 / 19806),

[0076] - Transgenic crop plants resistant to certain herbicides of the glufosinate type (e.g., see EP-A-0242236, EP-A-242246), glyphosate type (WO 92 / 00377), or sulfonylurea type (EP-A-0257993, US-A-5013659),

[0077] - Transgenic crop plants, such as cotton, for example, capable of producing Bacillus thuringiensis toxin (Bt toxin) that confers resistance to specific pests,

[0078] - Transgenic crop plant with modified fatty acid composition (WO 91 / 13972),

[0079] - Genetically modified crop plants having novel components or secondary substances that increase disease resistance, e.g., novel phytoalexins (EPA 309862, EPA0464461),

[0080] - Genetically modified plants with reduced photorespiration, resulting in high yields and high stress tolerance (EPA 0305398),

[0081] - Transgenic crop plants that produce pharmaceutically or diagnostically important proteins ("molecular pharming"),

[0082] - Transgenic crop plants characterized by higher yields or superior quality,

[0083] - For example, a transgenic crop plant ("gene stacking") characterized by a combination of the novel traits mentioned above.

[0084] A number of molecular biology techniques that can be used to produce novel transgenic plants with modified characteristics are known in principle; see, for example, I. Potrykus and G. Spangenberg (editor) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431.

[0085] For such genetic manipulation, nucleic acid molecules that enable mutagenic or sequence alteration by recombination of the DNA sequence can be introduced into the plasmid. With the help of standard methods, it is possible, for example, to perform base exchanges, remove parts of the sequence, or add 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., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker “Gene und Klone” [Genes and Clones], VCH Weinheim, 2nd ed., 1996.

[0086] The generation of plant cells with reduced activity of the gene product can be achieved, for example, through the expression of at least one corresponding antisense RNA, the expression of a sense RNA to achieve a co-inhibitory effect, or the expression of at least one appropriately configured ribozyme that specifically cleaves the transcript of the aforementioned gene product. This can be accomplished using a DNA molecule containing the entire coding sequence of the gene product, including any possible flanking sequence, or using a DNA molecule containing only a portion of the coding sequence, in which case these portions must be long enough to have an antisense effect in the cell. It is also possible to use a DNA sequence that has a high degree of homology to the coding sequence of the gene product but is not exactly identical to it.

[0087] When nucleic acid molecules are expressed in plants, the synthesized protein can be localized to any desired compartment of the plant cell. However, to achieve localization in a specific compartment, for example, a coding region can be linked to a DNA sequence that guarantees localization in that specific compartment. Such sequences are known to those skilled in the art (see, e.g., 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). The expression of nucleic acid molecules can also occur in organelles of plant cells.

[0088] Transgenic plant cells can be regenerated by known technology to produce whole plants. In principle, transgenic plants can become any desired plant species, namely not only monocotyledonous plants but also dicotyledonous plants.

[0089] In this way, a transgenic plant with altered characteristics can be obtained through the overexpression, repression, or inhibition of homologous (=natural) genes or gene sequences, or the expression of heterologous (=foreign) genes or gene sequences.

[0090] The compounds of the present invention may preferably be used in transgenic crops resistant to growth regulators, such as dicamba, for example, or herbicides that inhibit essential plant enzymes, such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS), or hydroxyphenylpyruvate deoxygenase (HPPD), or herbicides in the group consisting of sulfonylurea, glyphosate, glufosinate, or benzoylisoxazole and similar active ingredients.

[0091] When the active ingredient of the present invention is used in transgenic crops, in addition to the effects on harmful plants observed in other crops, effects specific to application in specific transgenic crops often occur, such as a change or specific expansion of the spectrum of weeds that can be controlled, a change in the dosage available for application, preferably excellent compatibility with herbicides to which the transgenic crop is resistant, and an effect on the growth and yield of the transgenic crop plants.

[0092] Accordingly, the present invention also relates to the use of the compound of the present invention of formula (I) and / or its salt as a herbicide for controlling harmful plants in crops of useful plants or ornamental plants, or optionally in transgenic crop plants.

[0093] Uses according to the present invention for the control of harmful plants or the regulation of plant growth include cases where the active compound of formula (I) or its salt is formed only after application from a precursor substance ("prodrug") on a plant, within a plant, or in the soil.

[0094] The present invention also provides a use (in a method) of one or more compounds of formula (I) or salts thereof or compositions according to the present invention (defined below) for controlling harmful plants or regulating plant growth, comprising applying an effective amount of one or more compounds of formula (I) or salts thereof to a plant (harmful plants together with useful plants, where appropriate), plant seeds, in or on the soil where the plant is growing, or to a cultivation site.

[0095] The present invention also provides a herbicide and / or plant growth regulating composition characterized by the composition comprising the following:

[0096] (a) one or more compounds of formula (I) defined above and / or salts thereof, preferably one of the compositions identified as preferred or particularly preferred, in particular one or more compounds of formulas 1-1 to 1-33 defined above and / or salts thereof,

[0097] and

[0098] (b) One or more additional substances selected from group (i) and / or (ii):

[0099] (i) One or more additional agrochemically active substances, preferably selected from the group consisting of insecticides, mite-killing agents, nematicides, additional herbicides (i.e., those not corresponding to the formula (I) defined above), fungicides, phytotoxicity reducers, fertilizers and / or additional growth regulators,

[0100] (ii) One or more formulation adjuvants commonly used in crop protection.

[0101] The additional agrochemically active substance of component (i) of the composition of the present invention is preferably selected from the group of substances mentioned in “The Pesticide Manual”, 19th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021.

[0102] The herbicide or plant growth regulating composition of the present invention preferably comprises one, two, three, or more formulation adjuvants (ii) conventional in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film-forming agents, thickeners, inorganic salts, powdering agents, a carrier that is solid at 25°C and 1013 mbar, preferably an adsorbable granular inert material, a wetting agent, an antioxidant, a stabilizer, a buffering agent, an antifoaming agent, water, an organic solvent, preferably an organic solvent that is miscible with water in any proportion at 25°C and 1013 mbar.

[0103] The compounds of the present invention may be applied in the form of hydrated powders, emulsifiable concentrates, sprayable solutions, powder products, or granules in conventional formulations. Accordingly, the present invention also provides herbicidal and plant growth regulating compositions comprising the compounds of the present invention.

[0104] The compounds of the present invention may be formulated in various ways depending on the required biological and / or physicochemical parameters. Possible formulations include, for example, hydrated powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), powder products (DP), seed treatments, granules for spreading and soil application, granules in the form of microgranules (GR), spray granules, absorbent and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes.

[0105] These individual formulation types are known in principle, for example, Winnacker-K It is listed in chler, "Chemische Technologie" [Chemical technology], Vol. 7, C. Hanser Verlag Munich, 4th edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; and K. Martens, "Spray Drying" Handbook, 3rd edition 1979, G. Goodwin Ltd. London.

[0106] Necessary formulation adjuvants, such as inert substances, surfactants, solvents, and additional additives, are likewise known, 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; Schoenfeldt, "Grenzflaechenaktive thylenoxidaddukte" [Interface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976, Winnacker-K It is listed in chler, "Chemische Technologie" [Chemical technology], Vol. 7, C. Hanser Verlag Munich, 4th edition 1986.

[0107] Based on these formulations, it is also possible to manufacture combinations with other pesticide active substances, e.g., insecticides, mite control agents, herbicides, fungicides, and also phytotoxicity reducers, fertilizers, and / or growth regulators, e.g., in the form of finished product formulations or tank mixes. Suitable phytotoxicity reducers are, e.g., mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexil, and dichlormide.

[0108] The hydrated powder is a formulation that can be uniformly dispersed in water and, in addition to the active ingredient and diluent or inert substance, comprises ionic and / or nonionic surfactants (wetting agents, dispersants), e.g., polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkan sulfons, alkylbenzene sulfons, sodium lignosulfonates, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene sulfonate, or sodium oleoylmethyltaurate. To prepare the hydrated powder, the active herbicidal ingredient is finely ground in a conventional device, such as a hammer mill, blower mill, and air-jet mill, and is simultaneously or subsequently mixed with a formulation aid.

[0109] An emulsifying concentrate is prepared by adding one or more ionic and / or nonionic surfactants (emulsifiers) and dissolving the active ingredient in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of relatively high-boiling point aromatic compounds or hydrocarbons or organic solvents. Examples of emulsifiers that may be used are calcium alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

[0110] Powdered products are obtained by grinding the active ingredient together with a finely dispersed solid such as natural clay or diatomite, for example, talc, kaolin, bentonite, and pyrophyllite.

[0111] The suspension concentrate may be water-based or oil-based. These may be prepared, for example, by wet grinding with a commercial bead mill and the optional addition of a surfactant as already listed for the other formulation types.

[0112] An emulsion, for example, an oil-in-water emulsion (EW), can be prepared by using an aqueous organic solvent and a stirrer, a colloid mill, and / or a static mixer, optionally using a surfactant already listed for the other formulation types mentioned above.

[0113] Granules can be prepared by spraying an active ingredient onto a granular inert material capable of adsorption, or by applying an active ingredient concentrate to the surface of a carrier material such as sand, kaolinite, or a granular inert material using an adhesive such as, for example, polyvinyl alcohol, sodium polyacrylate, or mineral oil. A suitable active ingredient may also be granulated in a manner conventional for the manufacture of fertilizer granules, as a mixture with fertilizer if desired.

[0114] Water-dispersible granules are generally manufactured by conventional processes such as spray drying, fluid bed granulation, pan granulation, mixing using a high-speed mixer, and extrusion without solid inert material.

[0115] For the manufacture of pan granules, fluid bed granules, extruder granules and spray granules, refer, for example, to the processes in "Spray-Drying Handbook" 3rd edition 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pp. 147 et al.; and "Perry's Chemical Engineer's Handbook", 5th edition, McGraw-Hill, New York 1973, pp. 8-57.

[0116] For additional details regarding the formulations of crop protection agents, 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.

[0117] Agrochemical formulations generally contain 0.1 to 99 weight%, particularly 0.1 to 95 weight%, of the compound of the present invention.

[0118] In the hydrated powder, the concentration of the active ingredient is, for example, about 10 to 90 weight%, and the remainder up to 100 weight% consists of conventional formulation components. In the emulsifiable concentrate, the concentration of the active ingredient may be about 1 to 90 weight%, preferably 5 to 80 weight%. The powder formulation contains 1 to 30 weight% of the active ingredient, preferably usually 5 to 20 weight%; the sprayable solution contains about 0.05 to 80 weight% of the active ingredient, preferably 2 to 50 weight%. In the case of water-dispersible granules, the content of the active ingredient depends in part on whether the active compound is in liquid or solid form, and on what granulation aids, fillers, etc. are used. In the water-dispersible granules, the content of the active ingredient is, for example, between 1 and 95 weight%, preferably between 10 and 80 weight%.

[0119] Additionally, the mentioned active ingredient formulations optionally include, respectively, conventional adhesives, wetting agents, dispersants, emulsifiers, penetrating agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoaming agents, evaporation inhibitors and agents affecting pH and viscosity. Examples of formulation adjuvants are described in particular in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).

[0120] The compound of formula (I) or its salt may be used in combination with other pesticide active substances, e.g., insecticides, mite control agents, nematicides, herbicides, fungicides, phytotoxicity reducers, fertilizers, and / or growth regulators, either by itself or in the form of a formulation, e.g., a finished product formulation or a tank mix. The combination formulation may be prepared based on the aforementioned formulation, taking into account the physical properties and stability of the active ingredients to be combined.

[0121] Of particular interest is the selective control of harmful plants in crops of useful and ornamental plants. Although Compound (I) of the present invention has already demonstrated excellent or adequate selectivity in many crops, phytotoxicity may occur in some crops in principle, particularly in the case of mixtures with other less selective herbicides. In this regard, of particular interest is a combination of Compound (I) of the present invention comprising Compound (I) or a combination thereof with other herbicides or pesticides and a phytotoxicity reducer. A phytotoxicity reducer used in an toxically effective amount reduces the phytotoxic side effects of herbicides / pesticides used in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), sugar beets, sugarcane, rapeseed, cotton, and soybeans, preferably cereals.

[0122] The weight ratio of the herbicide (mixture) to the phytoremediator generally depends on the application rate of the herbicide and the efficacy of the phytoremediator and may vary within a wide range, for example, from 200:1 to 1:200, preferably from 100:1 to 1:100, particularly from 20:1 to 1:20. In a manner similar to compound (I) or a mixture thereof, the phytoremediator may be formulated with additional herbicide / pesticide and may be provided and used with the herbicide in the form of a finished product formulation or a tank mix.

[0123] For application, commercial forms of herbicide formulations or herbicide-phytorelief formulations are diluted in the usual manner if necessary, for example, in the case of hydrated powders, emulsified concentrates, dispersions, and water-dispersible granules, diluted with water. Formulations in powder form, granules for soil application or spraying, and sprayable solutions are usually not further diluted with other inert substances before application.

[0124] The application rate of the compound of formula (I) and / or its salt is influenced to some extent by external conditions such as temperature, humidity, etc. The application rate may vary within a wide range. For application as a herbicide to control harmful plants, the total amount of the compound of formula (I) and its salt is preferably in the range of 0.001 to 10.0 kg / ha, preferably in the range of 0.005 to 5 kg / ha, more preferably in the range of 0.01 to 1.5 kg / ha, and particularly preferably in the range of 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.

[0125] When a compound of formula (I) and / or a salt thereof is used as a plant growth regulator, for example as a stem stabilizer for a crop plant such as mentioned above, preferably a cereal plant such as wheat, barley, rye, triticale, millet, rice, or corn, the total application dose is preferably in the range of 0.001 to 2 kg / ha, preferably in the range of 0.005 to 1 kg / ha, particularly in the range of 10 to 500 g / ha, and very particularly preferably in the range of 20 to 250 g / ha. This applies to both pre-emergence and post-emergence application.

[0126] Application as a stem stabilizer can be carried out at various stages of plant growth. For example, it is advisable to apply it after tillering and at the start of elongation growth.

[0127] Alternatively, it is also possible to apply it as a plant growth regulator by treating seeds, which includes various techniques for seed powdering and coating. The application rate depends on the specific technique and can be determined in preliminary tests.

[0128] Combination partners that may be used for the compound of general formula (I) in mixed formulations or tank mixes are known active ingredients that act as plant growth regulators based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyrubylshikimate-3-phosphate synthase, glutamine synthase, p-hydroxyphenylpyruvate deoxygenase, phytoene desaturase, photosystem I, photosystem II, or protoporpyrinogen oxidase, or as known from, for example, 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 literature cited therein.

[0129] Examples of known herbicides or plant growth regulators that may be combined with compounds of General Formula (I) include the active ingredients listed below (compounds are referred to by their generic names, chemical names, or code numbers according to the International Organization for Standardization (ISO), and always include all forms of use such as acids, salts, esters, and isomers such as stereoisomers and optical isomers). The list includes one, and in some cases more than one, form of application as an example:

[0130] Acetochlor, asifluorphen, asifluorphen-methyl, asifluorphen-sodium, acloniphen, alachlor, alidochlor, alloxidim, alloxidim-sodium, ametrine, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachloro-potassium, aminocyclopyrachloro-methyl, aminopyralide, aminopyralide-dimethylammonium, aminopyralide-tripromin, amitrol, ammonium sulfamate, anirophos, asulam, asulam-potassium, asulam-sodium, atrazine, azaphenidine, azimsulfuron, beflubutamide, (S)-(-)-Beflubutamide, Beflubutamide-M, Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-potassium, Befluralin, Befuresate, Bensulfuron, Bensulfuron-methyl, Bensulide, Bentazone, Bentazone-sodium, Benzobicyclon, Benzophenap, Bicyclopyrone, Biphenox, Villanaphos, Villanaphos-sodium, Bipirazone, Bispiribac, Bispiribac-sodium, Bixrozone, Bromasil, Bromasil-lithium, Bromasil-sodium, Bromobutide, Bromofenoxim, Bromooxynil, Bromooxynil butyrate, Bromooxynil-potassium, Bromooxynil heptanoate and Bromooxynil octanoate, Busocinone, Butachlor, Butapenacil, Butamiphos, butenachlor, butralin, butroxidim, butylate, capenstroll, cambendichlor, carbetamide, carpentrazone, carpentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium, chloramben-sodium, chlorbromurone, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazone, chlorimurone, chlorimurone-ethyl, chlorophthalim, chlortolurone, chlorsulfuron, chlortal, chlortal-dimethyl, chlortal-monomethyl, sinidone, sinidone-ethyl, synmethylline, exo-(+)-synmethylline, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(-)-synmethylline, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, sinosulfuron, clasiphos, cletodim, clodinapop, clodinapop-ethyl, clodinapop-propagyl, clomazone, clomeprop, clopyralide, clopyralide-methyl, clopyralide-olamine, clopyralide-potassium, clopyralide-triformin, chloransulam, chloransulam-methyl, cumiluron, cyanamide, cyanazine, cycloate, cyclopyranil, Cyclopyrimorate, cyclosulfamurone, cycloxidim, cyhalopop, cyhalopop-butyl, cyfrazine, 2,4-D (and its ammonium, butotyl, butyl, choline, diethylammonium, dimethylammonium, diolamine, dovoxyl, dodecylammonium, etexyl, ethyl, 2-ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, heptyl, methyl, potassium, tetradecylammonium, triethylammonium, triisopropanolammonium, tripromine and trolamine salts), 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium, 2,4-DB-isoooctyl, 2,4-DB-potassium and 2,4-DB-sodium, dimuron (dymron), dalafone, dalafone-calcium, dalafone-magnesium, dalafone-sodium, dazomet, dazomet-sodium, n-decanol, 7-deoxy-D-cedoheptulose, desmedipharmam, detosyl pyrazolate (DTP), dicamba and its salts (e.g., dicamba biproamine, dicamba N,N-bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolamineammonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolamine, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine), diclobenyl, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-Oxazolidin-3-one, dichlorprop, dichlorprop-butothyl, dichlorprop-dimethylammonium, dichlorprop-ethexil, dichlorprop-ethylammonium, dichlorprop-isooctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-ethexil, dichlorprop-P-potassium, dichlorprop-sodium, dichlorpop, dichlorpop-methyl, dichlorpop-P, dichlorpop-P-methyl, dichlorsulam, dipenzoquart, dipenzoquart-methylsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, Dimesulfazet, Dimetachlor, Dimetamethrin, Dimethenamide, Dimethenamide-P, Dimetrasulfuron, Dinitramin, Dinoterb, Dinoterb-acetate, Diphenamide, Diquart, Diquart-Dibromide, Diquart-Dichloride, Dithiopyr, Diuron, DNOC, DNOC-Ammonium, DNOC-Potassium, DNOC-Sodium, Endothal, Endothal-Diammonium, Endothal-Dipotassium, Endothal-Disodium, Epirifenacil (S-3100), EPTC, Esprocarb, Ethalfluralin, Etametsulfuron, Etametsulfuron-Methyl, Ethiozin, Ethofumesate, Ethoxyfen, Ethoxyfen-Ethyl, Ethoxysulfuron, Ethobenzanide, F-5231, i.e., N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazole-1-yl]-phenyl]ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazole-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, phenoxaprop, phenoxaprop-P, phenoxaprop-ethyl, phenoxaprop-P-ethyl, phenoxasulfone, fenpyrazone, fenquinotrione, pentrazamide, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, Plazasulfuron, Florasulam, Florpirausifen, Florpirausifen-benzyl, Fluazipop, Fluazipop-butyl, Fluazipop-methyl, Fluazipop-P, Fluazipop-P-butyl, Flucarbazone, Flucarbazone-sodium, Flucetosulfuron,Fluchlorallin, Flufenacet, Flufenpyr, Flufenpyr-ethyl, Flumesulam, Flumiclorac, Flumiclorac-pentyl, Flumioxazine, Fluometurone, Flurenol, Flurenol-butyl, -dimethylammonium and -methyl, Fluoroglycopene, Fluoroglycopene-ethyl, Flupropanate, Flupropanate-sodium, Flupyrsulfuron, Flupyrsulfuron-methyl, Flupyrsulfuron-methyl-sodium, Fluridone, Flurochloridone, Fluroxipyr, Fluroxipyr-butomethyl, Fluroxipyr-mephyl, Flurtamone, Fluthiacet, Fluthiacet-methyl, Pomesafen, Pomesafen-sodium, Foramsulfuron, Foramsulfuron-sodium, Fosamin, Fosamin-ammonium, Glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium, glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-sesquisodium and glyphosate-trimethium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl isopropylphosphoramidothioate, halausifen, halausifen-methyl, halosafene, halosulfurone, halosulfuron-methyl, Haloxypop, Haloxypop-P, Haloxypop-ethoxyethyl, Haloxypop-P-ethoxyethyl, Haloxypop-methyl, Haloxypop-P-methyl, Haloxypop-sodium, Hexazinone, HNPC-A8169, i.e., Prop-2-in-1-yl (2S)-2-{3-[(5-tert-butylpyridine-2-yl)oxy]phenoxy}propanoate, HW-02, i.e., 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, Hydantocidin, Icapolin, Icapolin-methyl, Imazametabenz, Imazametabenz-methyl, Imazamox, Imazamox-ammonium, Imazapic, Imazapic-ammonium, Imazapyr, Imazapyr-isopropylammonium, Imazaquin, Imazaquin-ammonium, Imazaquin-methyl, Imazetapyr, Imazetapyr-ammonium, Imazosulfuron, Indanophan, Indaziflam, Indolausiphyr, Iodosulfuron, Iodosulfuron-methyl,Iodosulfuron-methyl-sodium, oxynyl, oxynyl-lithium, -octanoate, -potassium and -sodium, ifencarbazone, iftriazopyride, i.e., 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazole-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo-[4,3-a]pyridine-8-carboxamide, isoproturone, isourone, isosaben, isosaflutol, carbutylate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, Ketospiradox-potassium, lactofen, renasil, linuron, MCPA, MCPA-butotyl, -butyl, -dimethylammonium, -diolamine, -2-ethylhexyl, -ethyl, -isobutyl, -isooctyl, -isopropyl, -isopropylammonium, -methyl, -olamine, -potassium, -sodium and -trolamine, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethexil, mecoprop-ethadyl, mecoprop-isooctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium, and mecoprop-trolamine, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, Mefenacet, mefluid, mefluid-diolamine, mefluid-potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron-sodium, mesotrion, metabenzthiazuron, metam, metamipop, metamitron, metazalocro, metazosulfuron, metabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metorachlor, S-metorachlor, methoselam, methoxuron, metproxybicyclone, metrivuzine, metsulfuron, metsulfuron-methyl, molynate, monolinuron, 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,Nicosulfurone, Nonanoic acid (Pelargonic acid), Norflurazone, Oleic acid (fatty acid), Orbencarb, Ortosulfamurone, Oryzalin, Oxadiargyl, Oxadiazone, Oxasulfuron, Oxaziclomefon, Oxyfluorphen, Paraquat, Paraquat-Dichloride, Paraquat-Dimethylsulfate, Febulate, Pendimethalin, Phenoxulam, Pentachlorophenol, Pentoxazone, Fetoxamide, Petroleum oil, Penmedipham, Penmedipham-Ethyl, Picloram, Picloram-Dimethylammonium, Picloram-Etexil, Picloram-Isooctyl, Picloram-Methyl, Picloram-Olamine, Picloram-Potassium, Picloram-Triethylammonium, Picloram-Tripromin, Picloram-Trolamine, Picolinaphen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron, Primisulfuron-methyl, Prodiamine, Propoxydim, Prometone, Promethrin, Propachlor, Propanyl, Propakizapop, Propazine, Propam, Propisochlor, Propoxycarbazone, Propoxycarbazone-sodium, Propirisulfuron, Propizamide, Prosulfocarb, Prosulfuron, Pyraclonil, Piraflufen, Piraflufen-ethyl, Pyraquinate, Pyrasulfotol, Pyrazolinate (Pyrazolate), Pyrazosulfuron, Pyrazosulfuron-ethyl, Pyrazosifene, Piribambenz, Piribambenz-isopropyl, Piribambenz-propyl, Pyribenzosim, Pyributicab, Pyridapol, Pyridate, Pyriftalide, Pyriminobac, Pyriminobac-methyl, Pyrimisulfan, Pyritiobac, Pyritiobak-sodium, piroxasulfone, piroxulam, quinclolac, quinclolac-dimethylammonium, quinclolac-methyl, quinmerac, quinoclamin, quizalopop, quizalopop-ethyl, quizalopop-P, quizalopop-P-ethyl, quizalopop-P-tefuril, QYM201, i.e., 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazole-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, rimisosaphen, rimsulfuron, saflufenacil, cetoxydim, siduron, simazine, cymetrin, SL-261, sulfotrione, sulfentrazone, sulfometurone, sulfometurone-methyl, sulfosulfuron, SYP-249,That is, 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, that is, 1-[7-fluoro-3-oxo-4-(prop-2-in-1-yl)-3,4-dihydro-2H-1,4-benzozozane-6-yl]-3-propyl-2-thiochiimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, e.g., TCA-ammonium, TCA calcium, TCA ethyl, TCA magnesium, TCA sodium, tebutiurone, tefuryltrione, tembotrone, tefraroxidim, terbasyl, terbucarb, terbumetone, terbutylazine, terbutrin, Tetflupyrrolimet, Taxtomin, Tenylchlor, Thiazopyr, Tiencarbazone, Tiencarbazone-methyl, Tifensulfuron, Tifensulfuron-methyl, Thiobencarb, Tiafenacil, Torpyralate, Topramesone, Tralcoccidim, Triapamon, Tri-alate, Triasulfuron, Triaziflam, Tribenuron, Tribenuron-methyl, Triclopyr, Triclopyr-butotyl, Triclopyrcholine, Triclopyr-ethyl, Triclopyr-triethylammonium, Triethazine, Trifloxysulfuron, Trifloxysulfuron-sodium, Triludimosazine, Triluralin, Trifloxysulfuron, Trifloxysulfuron-methyl, Tritosulfuron, Ureasulfate, Vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidine-2-yl)oxy]benzyl}aniline, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidine-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-methyl carboxylate ester, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidine-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-ethyl carboxylate ester, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidine-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazolo-5-carboxylic acid,Ethyl [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}pyridine-2-yl)oxy]acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl 5-chloropyrimidine-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazine-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridine-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazole-4-yl)(3,3,4-trimethyl-1,1-deoxydo-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-deoxydo-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazole-5-yl propane-1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazole-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazole-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate; Cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, prop-2-in-1-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, ethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indole-6-yl)pyridine-2-carboxylate, methyl 6-(1-acetyl-7-fluoro-1H-indole-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[1-(2,2-Dimethylpropanoyl)-7-fluoro-1H-indole-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indole-6-yl]pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylate, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-1,2-oxazole-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-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-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazolin-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidine-2-yl)pyridazine-1-ium salt (with a suitable anion, e.g., chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazine-3-yl)pyridazine-1-ium salt (with a suitable anion, e.g., chloride, acetate, or trifluoroacetate), 4-(pyrimidine-2-yl)-1-(2-sulfoethyl)pyridazine-1-ium salt (with a suitable anion, e.g., chloride, acetate, or trifluoroacetate),4-(pyridazine-3-yl)-1-(2-sulfoethyl)pyridazine-1-ium salt (with a suitable anion, e.g., chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazole-2-yl)pyridazine-1-ium salt (with a suitable anion, e.g., chloride, acetate, or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3,4-thiadiazole-2-yl)pyridazine-1-ium salt (with a suitable anion, e.g., chloride, acetate, or trifluoroacetate), methyl (2R)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, methyl (2R / S)-2-{[(E)-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}methylidene)amino]oxy}propanoate, (E)-2-(trifluoromethyl)benzaldehyde O-{2,6-bis[(4,6-dimethoxypyrimidine-2-yl)oxy]benzoyl}oxime, 2-fluoro-N-(5-methyl-1,3,4-oxadiazole-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanecarboxylic acid, 2-ethoxy-2-oxoethyl-1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}cyclopropanecarboxylate, 2-methoxy-2-oxoethyl-1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}cyclopropanecarboxylate, {[(1-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}cyclopropyl)carbonyl]oxy}acetic acid, 2-(2-bromo-4-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, methyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylate, ethyl 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylate, methyl-3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}-6-methyl-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylate, 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}-6-methyl-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylic acid, 3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenyl}-3a,4,5,6-tetrahydro-6aH-cyclopenta[d][1,2]oxazole-6a-carboxylic acid abscisic acid and related analogs [e.g. (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, methyl (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoate, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid, methyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1.0]hept-3-en-2-yl)-3-methylpenta-2,4-dienoic acid], acibenzola, acibenzola-S-methyl, S-adenosylhomocysteine, 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, (cyclohexylidene)aminooxyacetic acid 2-(isopropyloxy)-2-oxoethyl ester], 1-aminocycloprop-1-ylcarboxylic acid, N-methyl-1-aminocyclopropyl-1-carboxylic acid, 1-aminocyclopropyl-1-carboxamide, substituted 1-aminocyclopropyl-1-carboxylic acid derivatives listed in DE3335514, EP30287, DE2906507 or US5123951, 1-aminocyclopropyl-1-hydroxylic acid, 5-aminolevulinic acid, anthimidol, 6-benzylaminopurine, bikinine, brassinolide, brassinolide-ethyl, L-canaline, catechol, and Catechol (e.g., (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-cromene-3,5,7-triol), chitooligosaccharide (CO; CO differs from LCO in that it does not have the characteristic fatty acid side chains attached. CO is, in some cases, referred to as N-acetylchitooligosaccharide and is also composed of GlcNAc units but chitin molecules [(C8H, 13 NO5) n , CAS No. 1398-61-4] and chitosan molecule [(C5H 11 NO4) n, having a side chain distinct from CAS No. 9012-76-4), chitin-like compounds, chlormequat chloride, chlorprop, 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-cyclopropphenylmethanol, daminozide, dazomet, dazomet-sodium, n-decanol, dikegulac, dikegulac-sodium, endotal, endotal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, 1-ethylcyclopropene, flumetralin, fluorenol, Flurenol-butyl, fluorenol-methyl, flurprimidol, forchlorfenurone, gibberellic acid, inabenpid, indole-3-acetic acid (IAA), 4-indole-3-ilbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid ester or other derivative (e.g., methyl jasmonate, ethyl jasmonate), lipochitooligosaccharide (LCO, also referred in some cases as the symbiotic nodule formation signal (Nod or Nod factor) or Myc factor), composed of an oligosaccharide backbone consisting of a β-l,4-linked N-acetyl-D-glucosamine residue ("GlcNAc") having an N-attached fatty acid side chain fused to the non-reducing end.As can be inferred from the literature, LCOs differ in the number of GlcNAc units in the skeletal structure, the length and saturation of fatty acid chains, and the substitution of reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic acid hydrazide, mepiquot chloride, mepiquot pentaborate, 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-indeno[1,2-b]furan-2-one and related lactones listed in EP2248421, 2-(1-naphthyl)acetamid, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenoxide mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid and salts thereof (e.g., sodium 4-phenylbutanoate, potassium 4-phenylbutanoate), phenylalanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, 1-n-propylcyclopropene, putrescine, prohydrojasmon, ryzovitoxin, salicylic acid and methyl salicylate, sarcosine, sodium cycloprop-1-en-1-yl acetate, sodium cycloprop-2-en-1-yl acetate, sodium 3-(cycloprop-2-en-1-yl)propanoate, sodium 3-(cycloprop-1-en-1-yl)propanoate, sidefungin, spermidine, spermine, strigolactone, technagen, tidiazuron, triacontanol, trinessapac, trinessapac-ethyl, tryptophan, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine, 2-chloro-N-(3-methoxyphenyl)-9H-purine-6-amine.

[0131] Weakness-reducing agents likewise suitable as combination partners for the compound of the present invention of formula (I) include, for example, the following:

[0132] S1) Compound of chemical formula (S1)

[0133]

[0134] Here, the symbol and exponent are defined as follows:

[0135] n A is a natural number from 0 to 5, preferably a natural number from 0 to 3;

[0136] R A 1 is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro, or (C1-C4)-haloalkyl;

[0137] W A is an unsubstituted or substituted 2-way heterocyclic radical selected from the group consisting of partially unsaturated or aromatic 5-membered heterocycles having 1 to 3 cyclic heteroatoms selected from the group consisting of N and O, wherein at least one nitrogen atom and at most one oxygen atom are present in the ring, and preferably (W A 1 ) to (W A 5 It is a radical selected from the group consisting of ), and

[0138]

[0139] m A is 0 or 1 and;

[0140] R A 2 is OR A 3 , SR A 3 or NR A 3 R A4 Or, a saturated or unsaturated 3 to 7-membered heterocycle having at least one nitrogen atom and up to three heteroatoms, preferably heteroatoms selected from the group consisting of O and S, which is attached to the carbonyl group of (S1) through the nitrogen atom and is unsubstituted or substituted with a radical selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy, or optionally substituted phenyl, preferably formula OR A 3 , NHR A 4 or N(CH3)2 radicals, especially the chemical formula OR A 3 It is a radical of;

[0141] R A 3 is a hydrogen or unsubstituted or substituted aliphatic hydrocarbon radical, preferably a radical having a total of 1 to 18 carbon atoms;

[0142] R A 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, or substituted or unsubstituted phenyl;

[0143] R A 5 is H, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, cyano or COOR A 9 and, here R A 9 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;

[0144] R A 6 , R A 7 , RA 8 are identical or different, respectively hydrogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C3-C 12 )-cycloalkyl or substituted or unsubstituted phenyl and;

[0145] R A 10 H, (C3-C 12 )-cycloalkyl, substituted or unsubstituted phenyl or substituted or unsubstituted heteroaryl;

[0146] Preferably:

[0147] a) Dichlorophenylpyrazolin-3-carboxylic acid type (S1 a Compounds of ), preferably 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylate (S1-1)("mefenpyr-diethyl") and related compounds described in WO-A-91 / 07874;

[0148] b) Dichlorophenylpyrazolcarboxylic acid (S1 b Derivatives of ), preferably compounds such as 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 described in EP-A-333 131 and EP-A-269 806;

[0149] c) 1,5-Diphenylpyrazole-3-carboxylic acid (S1 cDerivatives of ), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5) and methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6), and related compounds, for example, described in EP-A-268554;

[0150] d) Triazole carboxylic acid type (S1 d Compounds of ), preferably phenchlorazole (ethyl ester), i.e., compounds such as ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-7) and related compounds described in EP-A-174 562 and EP-A-346 620;

[0151] e) 5-benzyl- or 5-phenyl-2-isoxazolin-3-carboxylic acid type or 5,5-diphenyl-2-isoxazolin-3-carboxylic acid type (S1 e As a compound of ), preferably ethyl 5-(2,4-dichlorobenzyl)-2-isoxazolin-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazolin-3-carboxylate (S1-9) and related compounds described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazolin-3-carboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazolin-3-carboxylate (S1-11) ("isoxadipen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazolin-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazolin-3-carboxylate (S1-13), patent application As described in WO-A-95 / 07897;

[0152] f) Type of triazolioxyacetic acid derivative (S1 fA compound of ), preferably methyl {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetate (S1-14) or {[1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetic acid (S1-15) or methyl {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetate (S1-16) or {[5-(4-chloro-2-fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetic acid (S1-17) or methyl Compounds such as {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetate (S1-18) or {[1-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1H-1,2,4-triazole-3-yl]oxy}acetic acid (S1-19), as described in patent application WO2021 / 105101.

[0153] S2) Quinoline derivative of chemical formula (S2),

[0154]

[0155] Here, the symbol and exponent are defined as follows:

[0156] R B 1 is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro, or (C1-C4)-haloalkyl;

[0157] n B is a natural number from 0 to 5, preferably a natural number from 0 to 3;

[0158] R B 2 is OR B 3 , SR B 3 or NR B 3 RB 4 or is a saturated or unsaturated 3 to 7-membered heterocycle having at least one nitrogen atom and up to three heteroatoms, preferably heteroatoms selected from the group consisting of O and S, which is attached to the carbonyl group of (S2) through the nitrogen atom and is unsubstituted or substituted with a radical selected from the group consisting of (C1-C4)-alkyl, (C1-C4)-alkoxy, or optionally substituted phenyl, preferably formula OR B 3 , NHR B 4 or N(CH3)2 radicals, especially the chemical formula OR B 3 It is a radical of;

[0159] R B 3 It is a hydrogen or unsubstituted or substituted aliphatic hydrocarbon radical, preferably a radical having a total of 1 to 18 carbon atoms;

[0160] R B 4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-alkoxy, or substituted or unsubstituted phenyl;

[0161] T B is an unsubstituted (C1-C4)-alkyl radical or a (C1 or C2)-alkanedyl chain substituted with a [(C1-C3)-alkoxy]carbonyl;

[0162] Preferably:

[0163] a) 8-quinolineoxyacetic acid type (S2 aCompounds of ), preferably 1-methylhexyl(5-chloro-8-quinolineoxy)acetate ("chloroquintocet-mexyl") (S2-1), 1,3-dimethylbut-1-yl(5-chloro-8-quinolineoxy)acetate (S2-2), 4-allyloxybutyl(5-chloro-8-quinolineoxy)acetate (S2-3), 1-allyloxyprop-2-yl(5-chloro-8-quinolineoxy)acetate (S2-4), ethyl(5-chloro-8-quinolineoxy)acetate (S2-5), methyl(5-chloro-8-quinolineoxy)acetate (S2-6), allyl(5-chloro-8-quinolineoxy)acetate (S2-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolineoxy)acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolineoxy)acetate (S2-9) and related compounds listed in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366, also (5-chloro-8-quinolineoxy)acetic acid (S2-10) listed in WO-A-2002 / 34048 and its hydrates and salts, e.g., lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts;

[0164] b) (5-chloro-8-quinolineoxy)malonic acid type (S2 b Compounds of ), preferably compounds such as diethyl (5-chloro-8-quinoline oxy)malonate, diallyl (5-chloro-8-quinoline oxy)malonate, methyl ethyl (5-chloro-8-quinoline oxy)malonate and related compounds described in EP-A-0 582 198.

[0165] S3) Compound of chemical formula (S3)

[0166]

[0167] Here, the symbol and exponent are defined as follows:

[0168] R C 1 It is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl;

[0169] R C 2 , R C 3 is the same or different and is each 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, dioxolanyl-(C1-C4)-alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R C 2 and R C 3 It forms a substituted or unsubstituted heterocyclic ring together, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine, or benzoxazine ring; preferably, an active ingredient of the dichloroacetamide type, which is frequently used, for example, as a pre-emergence phytotoxicity reducer (soil-acting phytotoxicity reducer), for example

[0170] "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), Stauffer's "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2), Stauffer's "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazane) (S3-4), PPG Industries' "PPG-1292" (N-allyl-N-[(1,3-dioxolane-2-yl)methyl]dichloroacetamide) (S3-5), Sagro-Chem's "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6), Nitrokemia or Monsanto's "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane) (S3-7), TRI-Chemical RT's "TI-35" (1-dichloroacetylasepan) (S3-8), BASF's "Diclonon" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9) ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one), "Furillazole" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-11).

[0171] S4) N-acylsulfonamide of chemical formula (S4) and its salt,

[0172]

[0173] In the above formula, the symbol and the exponent are defined as follows:

[0174] X D is CH or N;

[0175] R D 1 CO-NR D5 R D 6 or NHCO-R D 7 And;

[0176] R D 2 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;

[0177] R D 3 It is hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, or (C2-C4)-alkynyl;

[0178] R D 4 is a 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;

[0179] R D 5 v is selected from the group consisting of hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl, phenyl, or nitrogen, oxygen, and sulfur. D It is a 3 to 6-membered heterocyclile containing 7 heteroatoms, wherein the latter 7 radicals are selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C2)-alkylsulfinyl, (C1-C2)-alkylsulfonyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxycarbonyl, (C1-C4)-alkylcarbonyl, and phenyl. DIt is substituted with several substituents, and in the case of cyclic radicals, it is also substituted with (C1-C4)-alkyl and (C1-C4)-haloalkyl;

[0180] R D 6 is hydrogen, (C1-C6)-alkyl, (C2-C6)-alkenyl, or (C2-C6)-alkynyl, where the latter three radicals are selected from the group consisting of halogen, hydroxyl, (C1-C4)-alkyl, (C1-C4)-alkoxy, and (C1-C4)-alkylthio. D It is replaced by radicals, or

[0181] R D 5 and R D 6 It forms a pyrrolidinyl or piperidinyl radical together with a nitrogen atom possessing it;

[0182] R D 7 v is hydrogen, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the latter two radicals are selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy, and (C1-C4)-alkylthio. D It is substituted with several substituents, and in the case of cyclic radicals, it is also substituted with (C1-C4)-alkyl and (C1-C4)-haloalkyl;

[0183] n D is 0, 1, or 2;

[0184] m D is 1 or 2 and;

[0185] v D is 0, 1, 2, or 3;

[0186] Among these, the desirable one is, for example, the following chemical formula (S4 aIt is an N-acylsulfonamide type compound, which is known, for example, from WO-A-97 / 45016.

[0187]

[0188] In the above formula

[0189] R D 7 v is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the two latter radicals are selected from the group consisting of halogen, (C1-C4)-alkoxy, (C1-C6)-haloalkoxy, and (C1-C4)-alkylthio. D It is substituted with several substituents, and in the case of cyclic radicals, it is also substituted with (C1-C4)-alkyl and (C1-C4)-haloalkyl;

[0190] R D 4 is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;

[0191] m D is 1 or 2 and;

[0192] v D is 0, 1, 2, or 3;

[0193] Also, for example, the following chemical formula (S4 b Acylsulfamoylbenzamide of ) is also preferred, which is known, for example, from WO-A-99 / 16744,

[0194]

[0195] For example, the following

[0196] R D 5 = Cyclopropyl and (R D 4 ) = 2-OMe("Cyprosulfamide", S4-1),

[0197] R D5 = Cyclopropyl and (R D 4 ) = 5-Cl-2-OMe(S4-2),

[0198] R D 5 = Ethyl and (R D 4 ) = 2-OMe(S4-3),

[0199] R D 5 = Isopropyl and (R D 4 ) = 5-Cl-2-OMe(S4-4) and

[0200] R D 5 = Isopropyl and (R D 4 ) = 2-OMe(S4-5),

[0201] and chemical formula (S4 c Compounds of the N-acylsulfamoylphenylurea type of ) are also preferred, as is known, for example from EP-A-365484,

[0202]

[0203] In the above formula

[0204] R D 8 and R D 9 is independently hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, and

[0205] R D 4 is a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3, and

[0206] m D is 1 or 2;

[0207] for example

[0208] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,

[0209] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

[0210] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea.

[0211] S5) Active ingredients of the class of hydroxyaromatic and aromatic-aliphatic carboxylic acid derivatives (S5), e.g., ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001.

[0212] S6) Active ingredients of the class 1,2-dihydroquinoxalin-2-one (S6), e.g., 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thion, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one as described in WO-A-2005 / 112630.

[0213] S7) Compound of chemical formula (S7) described in WO-A-1998 / 38856,

[0214]

[0215] In the above formula, the symbol and the exponent are defined as follows:

[0216] R E 1 , R E 2 is independently a halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkyl, (C1-C4)-alkylamino, di-(C1-C4)-alkylamino, nitro;

[0217] A E is COOR E 3 or COSR E 4 And,

[0218] R E 3 , R E 4 Each is independently hydrogen, (C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C4)-alkynyl, cyanoalkyl, (C1-C4)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl, and alkylammonium, and

[0219] n E 1 is 0 or 1 and

[0220] n E 2 , n E 3 is independently 0, 1, or 2,

[0221] Preferably diphenylmethoxyacetic acid, ethyl diphenylmethoxyacetate, methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).

[0222] S8) A compound of formula (S8) as described in WO-A-98 / 27049,

[0223]

[0224] In the above formula

[0225] X F is CH or N,

[0226] n F is X FIf = N, it is an integer from 0 to 4 and

[0227] X F = In the case of CH, it is an integer from 0 to 5, and

[0228] R F 1 is a 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, and

[0229] R F 2 is hydrogen or (C1-C4)-alkyl, and

[0230] R F 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, wherein each of the aforementioned carbon-containing radicals is unsubstituted or substituted with one or more, preferably up to three, identical or different radicals selected from the group consisting of halogens and alkoxy, or a salt thereof.

[0231] Preferably the following compounds

[0232] X F is CH and,

[0233] n F is an integer from 0 to 2, and

[0234] R F 1 is a halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, and

[0235] R F 2 is hydrogen or (C1-C4)-alkyl, and

[0236] R F 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, or aryl, wherein each of the aforementioned carbon-containing radicals is unsubstituted or substituted with one or more, preferably up to three, identical or different radicals selected from the group consisting of halogens and alkoxy, or a salt thereof.

[0237] S9) Active ingredients of the 3-(5-tetrazolylcarbonyl)-2-quinolone (S9) class, e.g.

[0238] 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2) and 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999 / 000020.

[0239] S10) Chemical formula (S10 a ) or (S10 b ) compound

[0240] As described in WO-A-2007 / 023719 and WO-A-2007 / 023764

[0241]

[0242] In the above formula

[0243] R G 1 It is a halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3, and

[0244] Y G , Z G are independently O or S, and

[0245] n G is an integer from 0 to 4, and

[0246] R G 2 is (C1-C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl; benzyl, halobenzyl, and

[0247] R G 3 It is hydrogen or (C1-C6)-alkyl.

[0248] S11) Active ingredients of the oxyimino compound type (S11) known as seed treatment compositions, e.g., “oxabetrinil” ((Z)-1,3-dioxolalan-2-yl-methoxyimino(phenyl)acetonitrile) known as a seed treatment phytotoxicity reducer for millet damage caused by metolachlor (S11-1), “fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolalan-2-ylmethyl)oxime) known as a seed treatment phytotoxicity reducer for millet damage caused by metolachlor (S11-2), and “ciometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) known as a seed treatment phytotoxicity reducer for millet damage caused by metolachlor (S11-3).

[0249] S12) Active ingredients of the isothiochromate (S12) class, e.g., methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6)(S12-1) and related compounds of WO-A-1998 / 13361.

[0250] S13) One or more compounds of group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed treatment phytotoxicity reducer for corn damage caused by thiocarbamate herbicides; "Penchlorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a phytotoxicity reducer for pretilachlor in sowing rice; "Flurazole (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed treatment phytotoxicity reducer for millet damage caused by alachlor and metolachlor; "CL 304415" of American Cyanamid (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4), known as a phytotoxicity mitigator for corn damage caused by imidazolinone, Nitrokemia's "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5), known as a phytotoxicity mitigator for corn, Nitrokemia's "MG-838" (CAS Reg. No. 133993-74-5) (2-propenyl 1-oxa-4-azspiro[4.5]decane-4-carbodithioate) (S13-6), "Disulfotone" (O,O-diethyl S-2-ethylthioethyl phosphodithioate) (S13-7), "Dietolate" (O,O-diethyl O-phenyl phosphorothioate) (S13-8), "Mephenate" (4-chlorophenyl methyl carbamate) (S13-9).

[0251] S14) Active ingredients having phytotoxicity mitigating action on crop plants such as rice in addition to herbicidal action against harmful plants, for example, "Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethylpiperidin-1-carbothioate), known as a phytotoxicity mitigator for rice damage caused by molybdenum herbicides; "Dimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), known as a phytotoxicity mitigator for rice damage caused by imidazosulfuron herbicides; "Cumiluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, known as a phytotoxicity mitigator for rice damage caused by some herbicides; see JP-A-60087254); "Methoxyphenone" or known as a phytotoxicity mitigator for rice damage caused by some herbicides "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), Kumiai's "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) (CAS Reg. No. 54091-06-4), which is known as a phytotoxicity mitigator against damage caused by some herbicides in rice.

[0252] S15) Compound of chemical formula (S15) or its tautomer

[0253] As described in WO-A-2008 / 131861 and WO-A-2008 / 131860,

[0254]

[0255] In the above formula

[0256] R H 1 It is a (C1-C6)-haloalkyl radical, and

[0257] R H 2 is hydrogen or a halogen, and

[0258] R H 3 , R H 4 Each independently contains hydrogen, (C1-C16 )-alkyl, (C2-C 16 )-alkenyl or (C2-C 16 )-alkynyl, wherein each of the latter three radicals is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, hydroxy, 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 heterocyclil, or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl fused to a 4 to 6-membered saturated or unsaturated carbocyclic ring on one side of the ring, or 4 on one side of the ring (C4-C6)-cycloalkenyl fused to an to 6-membered saturated or unsaturated carbocyclic ring, wherein each of the latter four radicals is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, hydroxy, 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 heterocyclyl.

[0259] or

[0260] R H 3 is a (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkenyloxy, or (C2-C4)-haloalkoxy, and

[0261] R H 4 is hydrogen or (C1-C4)-alkyl, or

[0262] R H 3 and R H 4 It forms a 4 to 8-membered heterocyclic ring with a directly attached nitrogen atom, and this ring may further contain up to two additional cyclic heteroatoms in addition to the nitrogen atom, preferably selected from the group consisting of N, O, and S, and is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, and (C1-C4)-alkylthio.

[0263] S16) Active ingredients that are primarily used as herbicides but also have a phytotoxicity-reducing effect on crop plants, e.g., (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-methoxybenzoate (lactidichloro-ethyl).

[0264] The following examples illustrate the present invention. Specific details for implementing the invention

[0265] A. Chemical example

[0266] Synthesis of 2-chloro-4-cyclopropyl-3-(S-methylsulfonimidoyl)-N-(1,3,4-oxadiazole-2-yl)benzamide (Table Examples 1-4):

[0267] After adding 123.8 mg (1.58 mmol) of ammonium carbamate to a solution of 266.9 mg (0.79 mmol) of 2-chloro-4-cyclopropyl-3-(methylsulfanyl)-N-(1,3,4-oxadiazole-2-yl)benzamide in 4 ml of methanol, 638.3 mg (1.98 mmol) of iodosobenzene diacetate was added in fractions. The reaction mixture was stirred at room temperature for 20 hours, and then most of the solvent was removed using a rotary evaporator. The residue was purified by chromatography to obtain 106.7 mg (37.1%) of the target product.

[0268] Synthesis of 2-chloro-4-cyclopropyl-3-(methylsulfanyl)-N-(1,3,4-oxadiazole-2-yl)benzamide:

[0269] 0.50 g (1.82 mmol) of 2-chloro-4-cyclopropyl-3-(methylsulfanyl)benzoic acid, 0.17 g (2.00 mmol) of 1,3,4-oxadiazole-2-amine, and 3.0 ml of 3-methylpyridine were mixed with 0.30 g (3.64 mmol) of 1-methyl-1H-imidazole, 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 for 24 hours. For post-treatment, a saturated aqueous sodium chloride solution and dichloromethane were added, and after separating the organic phase, the solvent was removed under reduced pressure. The residue was purified by chromatography to obtain 267 mg (43.6%) of the target product as a colorless solid.

[0270] Synthesis of 2-methyl-3-(S-methylsulfonimidoyl)-N-(1,3,4-oxadiazole-2-yl)-4-(trifluoromethyl)-benzamide (Table Example Nos. 1-2):

[0271] 64.0 mg (0.82 mmol) of ammonium carbamate was added to a solution of 130.0 mg (0.41 mmol) of 2-methyl-3-(methylsulfanyl)-N-(1,3,4-oxadiazole-2-yl)-4-(trifluoromethyl)benzamide in 2 ml of methanol, followed by the fractional addition of 330.0 mg (1.02 mmol) of iodosobenzene diacetate. The reaction mixture was stirred at room temperature for 20 hours, after which most of the solvent was removed using a rotary evaporator. The residue was purified by chromatography to obtain 50.0 mg (33.3%) of the target product.

[0272] Synthesis of 4-(difluoromethyl)-2-ethyl-3-(S-ethylsulfonimidoyl)-N-(1,3,4-oxadiazole-2-yl)benzamide (Table Examples 1-6):

[0273] 88.2 mg (1.13 mmol) of ammonium carbamate was added to a solution of 185 mg (0.57 mmol) of 4-(difluoromethyl)-2-ethyl-3-(ethylsulfanyl)-N-(1,3,4-oxadiazole-2-yl)benzamide in 15 ml of methanol, followed by the fractional addition of 455 mg (1.41 mmol) of iodosobenzene diacetate. The reaction mixture was then stirred at room temperature for 20 hours. For post-treatment, a small amount of water was added, followed by sodium bisulfite. The solvent was mostly removed from the mixture using a rotary evaporator. The residue was taken in dichloromethane and a small amount of water. After phase separation, the organic phase was solvent-removed using a rotary evaporator. The residue was purified by chromatography to obtain 25.2 mg of a clean product.

[0274] Synthesis of 4-(difluoromethyl)-2-ethyl-3-(ethylsulfanyl)-N-(1,3,4-oxadiazole-2-yl)benzamide:

[0275] 634 mg (2.44 mmol) of 4-(difluoromethyl)-2-ethyl-3-(ethylsulfanyl)benzoic acid was heated to a temperature of 55°C to 60°C in 40 ml of dry tetrahydrofuran, and then 592 mg (3.65 mmol) of 1,1'-carbonyldiimidazole was added in portions. The reaction mixture was stirred under reflux for 3 hours. Subsequently, the contents were 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 an additional 4 hours. In the next step, 327 mg of 1,3,4-oxadiazole-2-amine (95% purity by weight; 3.65 mmol), 10 ml of acetonitrile, and 556 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene (3.65 mmol) were added sequentially at room temperature. The flask contents were stirred at room temperature for 3 days. To complete the reaction, the mixture was stirred at 50°C for an additional 5 hours, followed by the addition of 164 mg of 1,3,4-oxadiazole-2-amine (95% purity by weight; 1.83 mmol) and 278 mg of 1,8-diazabicyclo[5.4.0]undec-7-ene (1.83 mmol). The contents were stirred at room temperature for an additional 2 days. For post-treatment, the contents were placed in a rotary evaporator to remove most of the solvent. The residue was treated with water and dichloromethane. After phase separation, the aqueous phase was adjusted to pH 3 with dilute hydrochloric acid. Subsequently, the aqueous phase was extracted with dichloromethane. The combined organic phase was solvent-removed using a rotary evaporator. The residue was purified by chromatography to obtain 505 mg of a clean product.

[0276] The examples listed in the table below may be manufactured or obtained in a manner similar to the method mentioned above. The compounds listed in the table below are particularly preferred.

[0277] The abbreviations used mean the following:

[0278] Me = methyl Et = Ethyl c-Pr = cyclopropyl

[0279] Table 1: A compound of the present invention of general formula (I) in which R', R'' and W are each hydrogen.

[0280]

[0281]

[0282]

[0283] NMR data of selected examples: for selected examples of compounds of general formula (I) 1 H NMR data can be obtained in two ways, namely, (a) conventional NMR evaluation and interpretation or (b) according to the method described below 1 It is reported in the form of a list of H NMR peaks.

[0284] a) Conventional NMR interpretation

[0285] Example 1-10: 1 H-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).

[0286] Example 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).

[0287] Example 1-12: 1H-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).

[0288] Example 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).

[0289] Example 1-34: 1HNMR (CDCl3, δ, ppm): 8.17 (bs, 1H), 7.79 (d, 1H), 7.46-7.39 (m, 1H), 3.44 (s, 3H).

[0290] b) NMR peak list method

[0291] of the selected embodiment 1 H NMR data 1 It is 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. Pairs of δ and signal intensity values ​​for different signal peaks are separated from each other by semicolons.

[0292] Therefore, the peak list for one embodiment has the following form:

[0293] δ1(Strength 1); δ2(Strength 2);.....; δ i (robbery i );.......; δ n (robbery n )

[0294] The intensity of sharp signals correlates with the signal height (cm) in printed examples of NMR spectra and shows the actual ratio of signal intensity. For broad signals, multiple peaks or the center of the signal and their relative intensities can be displayed relative to the strongest signal in the spectrum.

[0295] 1 For chemical shift correction of H NMR spectra, particularly for spectra measured in DMSO, the chemical shift of tetramethylsilane and / or the solvent is used. Thus, the tetramethylsilane peak may be present in the NMR peak list, but it is not mandatory.

[0296] 1 The H NMR peak list is a typical 1 Since it is similar to the H NMR output, it generally includes all peaks listed in conventional NMR analysis.

[0297] Also, ordinary 1 Similar to 1H NMR outputs, these can show solvent signals and stereoisomer signals and / or impurity peaks of the target compound, which are likewise provided by the present invention.

[0298] When reporting a compound signal within the delta range of the solvent and / or water, the present invention 1 The H NMR peak list displays standard solvent peaks, for example, the DMSO peak and water peak in DMSO-D6, which usually have high intensity on average.

[0299] The stereoisomer and / or impurity peaks of the target compound usually have a lower intensity on average than the peak of the target compound (e.g., for purity > 90%).

[0300] These stereoisomers and / or impurities may be typical of a specific manufacturing process. Therefore, their peaks can help detect the reproducibility of the manufacturing process of the present invention based on a "by-product fingerprint."

[0301] Experts calculating the peaks of target compounds by known methods (MestreC, ACD simulations, and also empirically evaluated estimates) may separate the peaks of target compounds by optionally using additional intensity filters if necessary. Such separation is conventional 1 It is similar to the selection of each peak in H NMR analysis.

[0302] 1 Further details regarding the list of H NMR peaks can be found in Research Disclosure Database Number 564025.

[0303]

[0304]

[0305] B. Jejeye

[0306] a) 10 parts by weight of a compound of formula (I) and / or its salt and 90 parts by weight of talc as an inert substance are mixed, and the mixture is ground in a hammer mill to obtain a powder product.

[0307] b) 25 parts by weight of a compound of formula (I) and / or a salt thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate, and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant are mixed, and the mixture is ground in a pin mill to obtain a hydrated powder that is easily dispersed in water.

[0308] c) 20 parts by weight of the compound of formula (I) and / or its salt is mixed with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO), and 71 parts by weight of paraffinic mineral oil (boiling point range, e.g., about 255 to 277°C), and the mixture is ground to a fineness of less than 5 microns in a friction ball mill to obtain a dispersion concentrate that is easily dispersed in water.

[0309] d) An emulsifying concentrate is obtained from 15 parts by weight of a compound of formula (I) and / or a salt thereof, 75 parts by weight of cyclohexanone as a solvent, and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.

[0310] e) Water-dispersible granules are obtained by mixing the following.

[0311] 75 parts by weight of a compound of formula (I) and / or a salt thereof,

[0312] 10 parts by weight of calcium lignosulfonate,

[0313] 5 parts by weight of sodium lauryl sulfate,

[0314] 3 parts by weight of polyvinyl alcohol and

[0315] 7 parts by weight of kaolin,

[0316] The mixture is ground in a pin mill, and the powder is granulated in a fluidized bed by spraying water as a granulating liquid.

[0317] f) Water-dispersible granules are also obtained by homogenization and preliminary grinding in a colloid mill.

[0318] 25 parts by weight of a compound of formula (I) and / or a salt thereof,

[0319] 5 parts by weight of sodium 2,2'-dinapthylmethane-6,6'-disulfonate

[0320] 2 parts by weight of sodium oleoylmethyltaurate,

[0321] 1 part by weight of polyvinyl alcohol,

[0322] 17 parts by weight of calcium carbonate and

[0323] 50 parts by weight of water,

[0324] Then, the mixture is ground in a bead mill, and the resulting suspension is sprayed and dried in a spray tower using a single-phase nozzle.

[0325] C. Biological examples

[0326] 1. Post-emergence herbicidal activity and crop plant suitability

[0327] Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in sandy loam in plastic or wood fiber pots, covered with soil, and grown in a greenhouse under controlled growth conditions. Two to three weeks after sowing, test plants were treated at the one-leaf stage. Compounds of the present invention, formulated in the form of hydrated powder (WP) or emulsion concentrate (EC), were sprayed onto the green parts of the plants as an aqueous suspension or emulsion containing 0.5% additives under conditions corresponding to a water application rate of 600 l / ha. After maintaining the test plants in a greenhouse under optimal growth conditions for approximately three weeks, the activity of the formulation was visually evaluated by comparing it to an untreated control group. For example, 100% activity = plant death, 0% activity = same as the control plant.

[0328] Tables A1 to A14 below show the effects of selected compounds of General Formula (I) according to Table 1, obtained by the experimental procedure specified above, on various harmful plants at application doses of 80 g / ha or less. Appendices “a”, “b” and “c” are classified according to the dosages used on other harmful plants tested in the same manner.

[0329] Table A1a: Post-emergence effect (%) of ALOMY at 20 g / ha

[0330]

[0331] Table A1b: Post-emergence effect (%) of ALOMY at 80 g / ha

[0332]

[0333] Table A2a: Post-budding effect (%) of AMARE at 5 g / ha

[0334]

[0335] Table A2b: Post-emergence effect (%) of AMARE at 20 g / ha

[0336]

[0337] Table A2c: Post-emergence effect (%) of AMARE at 80 g / ha

[0338]

[0339] Table A3a: Post-emergence effect (%) of AVEFA at 20 g / ha

[0340]

[0341] Table A3b: Post-emergence effect (%) of AVEFA at 80 g / ha

[0342]

[0343] Table A4a: Post-emergence effect (%) of DIGSA at 5 g / ha

[0344]

[0345] Table A4b: Post-emergence effect (%) of DIGSA at 20 g / ha

[0346]

[0347] Table A4c: Post-emergence effect (%) of DIGSA at 80 g / ha

[0348]

[0349] Table A5a: Post-budding effect (%) of ECHCG at 5 g / ha

[0350]

[0351] Table A5b: Post-budding effect (%) of ECHCG at 20 g / ha

[0352]

[0353] Table A5c: Post-emergence effect (%) of ECHCG at 80 g / ha

[0354]

[0355] Table A6a: Post-budding effect (%) of LOLRI at 20 g / ha

[0356]

[0357] Table A6b: Post-budding effect (%) of LOLRI at 80 g / ha

[0358]

[0359] Table A7a: Post-budding effect (%) of MATIN at 5 g / ha

[0360]

[0361] Table A7b: Post-emergence effect (%) of MATIN at 20 g / ha

[0362]

[0363] Table A7c: Post-emergence effect (%) of MATIN at 80 g / ha

[0364]

[0365] Table A8a: Post-budding effect (%) of PHBPU at 5 g / ha

[0366]

[0367] Table A8b: Post-budding effect (%) of PHBPU at 20 g / ha

[0368]

[0369] Table A8c: Post-emergence effect (%) of PHBPU at 80 g / ha

[0370]

[0371] Table A9a: Post-emergence effect (%) of POLCO at 80 g / ha

[0372]

[0373] Table A10a: Post-budding effect (%) of SETVI at 5 g / ha

[0374]

[0375] Table A10b: Post-emergence effect (%) of SETVI at 20 g / ha

[0376]

[0377] Table A10c: Post-emergence effect (%) of SETVI at 80 g / ha

[0378]

[0379] Table A11a: Post-emergence effect (%) of VERPE at 5 g / ha

[0380]

[0381] Table A11b: Post-emergence effect (%) of VERPE at 20 g / ha

[0382]

[0383] Table A11c: Post-emergence effect (%) of VERPE at 80 g / ha

[0384]

[0385] Table A12a: Post-budding effect (%) of VIOTR at 5 g / ha

[0386]

[0387] Table A12b: Post-emergence effect (%) of VIOTR at 20 g / ha

[0388]

[0389] Table A12c: Post-emergence effect (%) of VIOTR at 80 g / ha

[0390]

[0391] Table A13a: Post-budding effect (%) of ABUTH at 5 g / ha

[0392]

[0393] Table A13b: Post-budding effect (%) of ABUTH at 20 g / ha

[0394]

[0395] Table A13c: Post-budding effect (%) of ABUTH at 80 g / ha

[0396]

[0397] Table A14a: Post-emergence effect (%) at 20 g / ha on KCHSC

[0398]

[0399] Table A14b: Post-emergence effect (%) on KCHSC at 80 g / ha

[0400]

[0401] Tables A15 to A19 below show the suitability of selected compounds of General Formula (I) according to Table 1 at application doses of 20 g / ha or less, observed in tests according to the specified experimental procedure above. The observed effects on selected crop plants are reported here in comparison to an untreated control (values ​​are %). Appendices "a", "b", and "c" are classified according to the dosages used on other crop plants tested in the same manner.

[0402] Table A15a: Post-budding effect (%) of ZEAMX at 5 g / ha

[0403]

[0404] Table A15b: Post-emergence effect (%) of ZEAMX at 20 g / ha

[0405]

[0406] Table A16a: Post-emergence effect (%) of TRZAS at 5 g / ha

[0407]

[0408] Table A16b: Post-emergence effect (%) of TRZAS at 20 g / ha

[0409]

[0410] Table A17a: Post-budding effect (%) of ORYSA at 5 g / ha

[0411]

[0412] Table A17b: Post-emergence effect (%) of ORYSA at 20 g / ha

[0413]

[0414] Table A18a: Post-budding effect (%) of GLXMA at 5 g / ha

[0415]

[0416] Table A18b: Post-budding effect (%) of GLXMA at 20 g / ha

[0417]

[0418] Table A19a: Post-emergence effect (%) at 5 g / ha on BRSNW

[0419]

[0420] Table A19b: Post-emergence effect (%) at 20 g / ha on BRSNW

[0421]

[0422] As the results show, for post-budding treatment, the compound of the present invention of general formula (I) at an application rate of 0.08 kg of active substance or less per hectare is used, for example, in Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Parvitis purpurea It has good herbicidal efficacy against harmful plants such as *Pharbitis purpurea* (PHBPU), *Polygonum convolvulus* (POLCO), *Setaria viridis* (SETVI), *Veronica persica* (VERPE), and *Viola tricolor* (VIOTR), and also has good crop suitability against organisms such as *Oryza sativa* (ORYSA), *Zea mays* (ZEAMX), *Brassica napus* (BRSNW), *Glycine max* (GLXMA), and *Triticum aestivum* (TRZAS) at application rates of 0.02 kg or less per hectare.

[0423] 2. Pre-emergence herbicidal action and crop plant suitability

[0424] Seeds of monocotyledonous and dicotyledonous weeds and crops were placed in plastic or organic growing pots and covered with soil. The compound of the present invention, formulated in the form of a hydrated powder (WP) or an emulsion concentrate (EC), was applied to the surface of the soil covered with an aqueous suspension or emulsion containing 0.5% additives under conditions corresponding to a water application rate of 600 l / ha. After treatment, the pots were placed in a greenhouse and maintained under favorable growth conditions suitable for the test plants. After approximately 3 weeks, the efficacy of the formulation was visually evaluated as a percentage compared to an untreated control group. For example, 100% activity = plant death, 0% activity = same as the control plant.

[0425] Tables B1 to B14 below show the effects of selected compounds of General Formula (I) according to Table 1, obtained by the experimental procedure specified above, on various harmful plants at application doses of 80 g / ha or less. Appendices “a”, “b”, and “c” are classified according to the dosages used on other harmful plants tested in the same manner.

[0426] Table B1a: Pre-emergence effect (%) of ALOMY at 80 g / ha

[0427]

[0428] Table B2a: Pre-emergence effect (%) on AMARE at 20 g / ha

[0429]

[0430] Table B2b: Pre-emergence effect (%) on AMARE at 80 g / ha

[0431]

[0432] Table B3a: Pre-emergence effect (%) of AVEFA at 20 g / ha

[0433]

[0434] Table B3b: Pre-emergence effect (%) of AVEFA at 80 g / ha

[0435]

[0436] Table B4a: Pre-emergence effect (%) of DIGSA at 20 g / ha

[0437]

[0438] Table B4b: Pre-emergence effect (%) of DIGSA at 80 g / ha

[0439]

[0440] Table B5a: Pre-emergence effect (%) of ECHCG at 20 g / ha

[0441]

[0442] Table B5b: Pre-emergence effect (%) of ECHCG at 80 g / ha

[0443]

[0444] Table B6a: Pre-emergence effect (%) of LOLRI at 80 g / ha

[0445]

[0446] Table B7a: Pre-emergence effect (%) of MATIN at 20 g / ha

[0447]

[0448] Table B7b: Pre-emergence effect (%) of MATIN at 80 g / ha

[0449]

[0450] Table B8a: Pre-emergence effect (%) of PHBPU at 20 g / ha

[0451]

[0452] Table B8b: Pre-emergence effect (%) of PHBPU at 80 g / ha

[0453]

[0454] Table B9a: Pre-emergence effect (%) of POLCO at 20 g / ha

[0455]

[0456] Table B9b: Pre-emergence effect (%) of POLCO at 80 g / ha

[0457]

[0458] Table B10a: Pre-emergence effect (%) of SETVI at 20 g / ha

[0459]

[0460] Table B10b: Pre-emergence effect (%) of SETVI at 80 g / ha

[0461]

[0462] Table B11a: Pre-emergence effect (%) of VERPE at 20 g / ha

[0463]

[0464] Table B11b: Pre-emergence effect (%) of VERPE at 80 g / ha

[0465]

[0466] Table B12a: Pre-emergence effect (%) of VIOTR at 20 g / ha

[0467]

[0468] Table B12b: Pre-emergence effect (%) of VIOTR at 80 g / ha

[0469]

[0470] Table B13a: Pre-emergence effect (%) of ABUTH at 20 g / ha

[0471]

[0472] Table B13b: Pre-emergence effect (%) of ABUTH at 80 g / ha

[0473]

[0474] Table B14a: Pre-emergence effect (%) at 20 g / ha on KCHSC

[0475]

[0476] Table B14b: Pre-emergence effect (%) at 80 g / ha on KCHSC

[0477]

[0478] Tables B15 to B19 below show the suitability of selected compounds of General Formula (I) according to Table 1 at application doses of 80 g / ha or less, observed in tests according to the specified experimental procedure above. The observed effects on selected crop plants are reported here in comparison to an untreated control (values ​​are %). Appendices "a", "b", and "c" are classified according to the dosages used on other crop plants tested in the same manner.

[0479] Table B15a: Pre-emergence effect (%) of ZEAMX at 20 g / ha

[0480]

[0481] Table B15b: Pre-emergence effect (%) of ZEAMX at 80 g / ha

[0482]

[0483] Table B16a: Pre-emergence effect (%) of TRZAS at 20 g / ha

[0484]

[0485] Table B16b: Pre-emergence effect (%) of TRZAS at 80 g / ha

[0486]

[0487] Table B17a: Pre-emergence effect (%) of ORYSA at 20 g / ha

[0488]

[0489] Table B18a: Pre-emergence effect (%) of GLXMA at 20 g / ha

[0490]

[0491] Table B18b: Pre-emergence effect (%) of GLXMA at 80 g / ha

[0492]

[0493] Table B19a: Pre-emergence effect (%) at 20 g / ha on BRSNW

[0494]

[0495] Table B19b: Pre-emergence effect (%) at 80 g / ha on BRSNW

[0496]

[0497] As the results show, for pre-budding treatment, the compound of the present invention of general formula (I) at an application rate of 0.08 kg of active substance or less per hectare is used, for example, in Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Parvitis purpurea It has good herbicidal efficacy against harmful plants such as *Pharbitis purpurea* (PHBPU), *Polygonum convolvulus* (POLCO), *Setaria viridis* (SETVI), *Veronica persica* (VERPE), and *Viola tricolor* (VIOTR), and also has good crop suitability against organisms such as *Oryza sativa* (ORYSA), *Zea mays* (ZEAMX), *Brassica napus* (BRSNW), *Glycine max* (GLXMA), and *Triticum aestivum* (TRZAS) at application rates of 0.08 kg or less per hectare.

[0498] 3. Comparative herbicidal effect and crop plant suitability of the compound of the present invention compared with a structurally similar known literature compound of WO2013 / 124228 before and after budding.

[0499] Table C1 below compares the compounds of the present invention with structurally similar compounds in known literature of WO2013 / 124228. Here, the compounds of the present invention are distinguished from the compounds known in the literature by differences in important structural features. Unlike the compounds known in the literature, the compounds of the present invention (1-1, 1-2, 1-7, 1-11, 1-13) do not possess any methyl substituents on the oxadiazole ring.

[0500] Table C1

[0501]

[0502] Tables C2-C11 below show the post-emergence effects of the compound of the present invention and a structurally similar known literature compound of WO2013 / 124228 on various harmful plants at application rates of 20 g / ha or less obtained by the experimental procedure specified above.

[0503] Table C2

[0504]

[0505] Table C3

[0506]

[0507] Table C4

[0508]

[0509] Table C5

[0510]

[0511] Table C6

[0512]

[0513] Table C7

[0514]

[0515] Table C8

[0516]

[0517] Table C9

[0518]

[0519] Table C10

[0520]

[0521] Table C11

[0522]

[0523] As shown in the results presented in Tables C2 to C11, the compounds of the present invention (1-1, 1-2, 1-7, 1-11), when compared to structurally similar compounds 7-18, 7-6, 7-17, and 7-12 known from the literature (WO2013 / 124228), at application doses of 20 g of active substance or less per hectare, Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Matricaria inodora (MATIN), and Parvitis purpurea (Pharbitis It has significantly improved post-emergence herbicidal efficacy against harmful plants such as purpurea (PHBPU), Setaria viridis (SETVI), Veronica persica (VERPE), and Viola tricolor (VIOTR).

[0524] Tables C12-C16 below show the post-budding crop plant suitability of the compound of the present invention and a structurally similar known literature compound of WO2013 / 124228 at application rates of 20 g / ha or less obtained by the experimental procedure specified above.

[0525] Table C12

[0526]

[0527] Table C13

[0528]

[0529] Table C14

[0530]

[0531] Table C15

[0532]

[0533] Table C16

[0534]

[0535] As shown in the results presented in Tables C12 to C16, the compounds of the present invention (1-7, 1-13) have significantly improved post-emergence suitability for the crop plants Brassica napus (BRSNW), Glycine max (GLXMA), Oryza sativa (ORYSA), Triticum aestivum (TRZAS), and Zea mays (ZEAMX) at application rates of 20 g or less per hectare, compared to structurally similar compounds 7-17 and 7-29 known from the literature (WO2013 / 124228).

[0536] Tables C17-C28 below show the pre-emergence effects of the compound of the present invention and a structurally similar known literature compound of WO2013 / 124228 on various harmful plants at application rates of 80 g / ha or less obtained by the experimental procedure specified above.

[0537] Table C17

[0538]

[0539] Table C18

[0540]

[0541] Table C19

[0542]

[0543] Table C20

[0544]

[0545] Table C21

[0546]

[0547] Table C22

[0548]

[0549] Table C23

[0550]

[0551] Table C24

[0552]

[0553] Table C25

[0554]

[0555] Table C26

[0556]

[0557] Table C27

[0558]

[0559] Table C28

[0560]

[0561] As shown in the results presented in Tables C17 to C28, the compounds of the present invention (1-1, 1-2, 1-7, 1-11), when compared to structurally similar compounds 7-18, 7-6, 7-17, and 7-12 known from the literature (WO2013 / 124228), at application doses of 80 g of active substance or less per hectare, Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), and Matricaria It has significantly improved pre-emergence herbicidal efficacy against harmful plants such as Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE), and Viola tricolor (VIOTR).

[0562] Tables C29-C32 below show the pre-emergence crop plant suitability of the compound of the present invention and a structurally similar known literature compound of WO2013 / 124228 at application rates of 80 g / ha or less obtained by the experimental procedure specified above.

[0563] Table C29

[0564]

[0565] Table C30

[0566]

[0567] Table C31

[0568]

[0569] Table C32

[0570]

[0571] As shown in the results presented in Tables C29 to C32, the compounds of the present invention (1-7, 1-13) have significantly improved pre-emergence suitability for the crop plants Brassica napus (BRSNW), Glycine max (GLXMA), Oryza sativa (ORYSA), and Zea mays (ZEAMX) at application rates of 80 g or less per hectare, compared to structurally similar compounds 7-17 and 7-29 known from the literature (WO2013 / 124228).

Claims

Claim 1 Sulfonimidoylbenzamide of chemical formula (I) or its salt: The symbols in the formula 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, (C3-C6)-cycloalkyl, and Z is a halogen, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, halo-(C1-C6)-alkoxy, (C1-C6)-alkylsulfonyl, and W is hydrogen, a halogen, and R is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, and R' is hydrogen, cyano, (C1-C6)-alkyl, and R'' is hydrogen, (C1-C6)-alkyl carbonyl. Claim 2 In paragraph 1, X ga is a halogen, (C1-C3)-alkyl, (C1-C3)-alkoxy, (C3-C6)-cycloalkyl, and Z ga halogen, (C1-C3)-alkyl, halogen-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, halo-(C1-C3)-alkoxy, and W is hydrogen, fluorine, and R This is a (C1-C3)-alkyl, and R' is hydrogen, and R'' Sulfonimidoylbenzamide or its salt, in which α is hydrogen. Claim 3 In paragraph 1 or 2, X ga is chlorine, methyl, ethyl, methoxy, cyclopropyl, and Z ga is chlorine, methyl, difluoromethyl, trifluoromethyl, cyclopropyl, trifluoromethoxy, and W is hydrogen, and R This is methyl, ethyl, and R' is hydrogen, and R'' Sulfonimidoylbenzamide or its salt, in which α is hydrogen. Claim 4 A herbicidal composition comprising at least one sulfonimidoylbenzamide according to any one of claims 1 to 3 as a mixture with a formulation adjuvant. Claim 5 A herbicidal composition according to claim 4, comprising at least one additional pesticide active substance from the group consisting of insecticides, mite-killing agents, herbicides, fungicides, phytotoxicity reducers, and growth regulators. Claim 6 A method for controlling unwanted plants, characterized by applying an effective amount of at least one sulfonimidoylbenzamide according to any one of claims 1 to 3 or a herbicidal composition according to claim 4 or 5 to a plant or a place of unwanted vegetation. Claim 7 Use of a sulfonimidoylbenzamide of formula (I) according to any one of claims 1 to 3 or a herbicidal composition according to claim 4 or 5 for the control of unwanted plants. Claim 8 In claim 7, the use is characterized by the sulfonimidoylbenzamide of chemical formula (I) being used to control unwanted plants in crops of useful plants. Claim 9 In paragraph 8, the use is characterized in that the useful plant is a transgenic useful plant.

Images