3-phenyl isoxazoline-5-formamide compound, and preparation method therefor, weeding composition thereof and use thereof

Abstract

The present invention belongs to the technical field of pesticides, and specifically relates to a 3-phenyl isoxazoline-5-formamide compound, and a preparation method therefor, a weeding composition thereof and the use thereof. The compound is as shown in general formula I, wherein X is hydrogen, alkyl, alkenyl, etc.; Y is hydrogen, alkyl, alkenyl, alkynyl, etc.; R1, R2, R3, R4 and R5 are independently selected from hydrogen, halogen, alkyl, etc.; and Z1, Z2 and Z3 independently represent hydrogen, halogen or alkyl. The compound has an excellent herbicidal activity and crop safety.

Description

3-phenylisoxazoline-5-carboxamide compounds, preparation method thereof, herbicidal composition and application TECHNICAL FIELD

[0001] The present application belongs to the technical field of pesticides, and particularly relates to a 3-phenylisoxazoline-5-carboxamide compound, a preparation method thereof, a herbicidal composition and application. BACKGROUND

[0002] The control of weeds is a crucial step in the process of achieving efficient agriculture. Although there are various types of herbicides on the market, the weed control performance of these known compounds on harmful plants and the selectivity on crops are not completely satisfactory. Due to the continuous expansion of the market, the resistance of weeds, the service life of drugs, the economy of drugs and other issues, and the increasing attention to the environment, scientists need to continuously research and develop new herbicides with high efficiency, safety, economy and different action modes. SUMMARY

[0003] The present application provides a 3-phenylisoxazoline-5-carboxamide compound, a preparation method thereof, a herbicidal composition and application. The compound has excellent herbicidal activity and crop safety.

[0004] The technical scheme adopted by the present application is as follows:

[0005] A 3-phenylisoxazoline-5-carboxamide compound or a salt thereof as shown in formula I:

[0006] X is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl or arylalkyl;

[0007] Y is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, -(CO)OR, -(CO)R, aryl, heterocyclyl; wherein the alkyl, alkenyl or alkynyl is optionally substituted with at least one group selected from halogen, cyano, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -OR, -SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2 or -(CO)N(R)(OR);

[0008] Z1, Z2 and Z3 independently represent hydrogen, halogen or alkyl;

[0009] R1, R2, R3, R4, R5, independently, represent hydrogen, halogen, alkyl, alkenyl, alkynyl, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -(CO)R, -(CO)N(R)2, -alkylene-OR, -alkylene-SR, -alkylene-SOR, -alkylene-(SO2)R, -alkylene-N(R)2, -alkylene-(CO)R, -alkylene-(CO)N(R)2, cyano, nitro, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl;

[0010] the aforementioned cycloalkyl, cycloalkenyl, aryl or heterocyclyl is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR, -SR, -alkylene-OR, -alkylene-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -SOR, -SO2R, -OSO2R or -N(R)2;

[0011] R, independently, represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted with at least one group selected from halogen, hydroxy, alkoxy, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

[0012] Preferably, X is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl or arylC1-C8 alkyl;

[0013] Y is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, -(CO)OR, -(CO)R, aryl, heterocyclyl; wherein C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted with at least one group selected from halogen, cyano, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -OR, -SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2 or -(CO)N(R)(OR);

[0014] Z1, Z2, Z3, independently, represent hydrogen, halogen or C1-C8 alkyl;

[0015] R1, R2, R3, R4, R5 each independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -(CO)R, -(CO)N(R)2, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -(C1-C8 alkylene)-SOR, -(C1-C8 alkylene)-(SO2)R, -(C1-C8 alkylene)-N(R)2, -(C1-C8 alkylene)-(CO)R, -(C1-C8 alkylene)-(CO)N(R)2, cyano, nitro, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, aryl, heterocyclyl, aryl C1-C8 alkyl or heterocyclyl C1-C8 alkyl;

[0016] the aforementioned C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclyl is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo C2-C8 alkynyl, -OR, -SR, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -SOR, -SO2R, -OSO2R or -N(R)2;

[0017] R each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted by at least one group selected from halogen, hydroxy, C1-C8 alkoxy, cyano or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo C1-C8 alkoxy.

[0018] In one embodiment, X is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl, or arylC1-C6 alkyl.

[0019] In one embodiment, Y is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, -(CO)OR, -(CO)R, aryl, heterocyclyl; wherein C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is optionally substituted with at least one group selected from halo, cyano, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -OR, -SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, or -(CO)N(R)(OR).

[0020] In one embodiment, Z1, Z2, Z3, independently represent hydrogen, halo, or C1-C6 alkyl.

[0021] In one embodiment, R1, R2, R3, R4, R5, independently represent hydrogen, halo, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -(CO)R, -(CO)N(R)2, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, -(C1-C6 alkylene)-SOR, -(C1-C6 alkylene)-(SO2)R, -(C1-C6 alkylene)-N(R)2, -(C1-C6 alkylene)-(CO)R, -(C1-C6 alkylene)-(CO)N(R)2, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, aryl, heterocyclyl, arylC1-C6 alkyl, or heterocyclylC1-C6 alkyl;

[0022] R is independently hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C6alkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy, or haloC1-C6alkoxy.

[0023] R is independently hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C6alkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy, or haloC1-C6alkoxy.

[0024] R is independently hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C6alkyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6alkyl, haloC1-C6alkyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfonyl, C1-C6alkoxy, or haloC1-C6alkoxy.

[0025] In the definitions of the compounds of the general formulae above and in all the formulae below, the terms used, whether used alone or in a compound word, represent the following substituents: Alkyl groups having more than two carbon atoms can be straight-chain or branched. As in the compound word "alkylene-OR", alkylene can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyl groups are, for example, C1 alkyl - methyl; C2 alkyl - ethyl; C3 alkyl - propyl, such as n-propyl or isopropyl; C4 alkyl - butyl, such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5 alkyl - pentyl, such as n-pentyl; C6 alkyl - hexyl, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, ethenyl, 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 is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bonds can be in any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bonds can be in any position. Halogen is fluorine, chlorine, bromine or iodine.

[0026] Unless specifically stated otherwise, the term "aryl" as used herein includes, but is not limited to, phenyl, naphthyl, The term "heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups The term "heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups

[0027] The term "optionally" or "optional" means that the subsequently described event or circumstance can or can not occur, and thus that description encompasses instances where the event or circumstance occurs and instances where it does not. For example, the term "optionally substituted" means that the specified atom or group is either unsubstituted or substituted with one or more substituents. If a group is substituted with a group, this is to be understood as meaning that the group is substituted with one or more groups, which are the same or different, selected from those mentioned. In addition, the same or different substituents contained in the same or different substituents are each selected independently of one another, either identically or differently. The same applies to ring systems formed from different atoms and units. At the same time, the scope of the claims is to exclude compounds which are chemically unstable under standard conditions, as known to the person skilled in the art.

[0028] In addition, unless specifically limited otherwise, the term "substituted" as used herein means substituted with one, two, three, four, or five groups; groups not marked with a specific position of attachment (including heterocyclyl, aryl, etc.) can be attached at any position, including attachment to a C or N; if it is substituted, the substituents can likewise be substituted at any position, as long as the valency rules are obeyed. For example, a heteroaryl group may represent etc.

[0029] If various functional groups are present, the application also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0030] wherein the carbon atom at position * is a chiral center, and Z1, Z2, Z3, R1, R2, R3, R4, R5, X and Y are as defined above;

[0031] has a stereochemical purity of 60-100% (S), preferably 70-100%, more preferably 80-100%, even more preferably 90-100%, and even more preferably 95-100%, based on the content of stereoisomers having the R and S configuration at position *; or has a stereochemical purity of 60-100% (R), preferably 70-100%, more preferably 80-100%, even more preferably 90-100%, and even more preferably 95-100%, based on the content of stereoisomers having the R and S configuration at position *.

[0032] wherein "stereochemical purity" means the amount of the stated stereoisomer as a percentage of the total amount of stereoisomers having a stereogenic center.

[0033] In the present application, the stereochemical configuration at position * in formula I' is determined according to the Cahn-Ingold-Prelog system, however the subject matter of the present application also relates to all stereoisomers of other positions included in formula I, and mixtures thereof. Such compounds of formula I include, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically mentioned in formula I. It is to be understood that the present application includes pure isomers and mixtures of isomers enriched to varying degrees, for example, the asymmetric carbon atom at position * is in the R configuration or the S configuration, or in mixtures, the compounds or likewise configured compounds have the R configuration or the S configuration at position *, or are present in proportions in which the compounds having the R configuration or the S configuration predominate (at least 60% of the configuration), while the other asymmetric carbon atoms can be present in racemic form, or can also be resolved to varying degrees. As long as the stereochemical configuration is met, possible stereoisomers defined by the particular spatial form, such as enantiomers, diastereomers, Z- and E-isomers, are included in formula I and can be obtained from mixtures of stereoisomers in a conventional manner, or can also be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.

[0034] The method for preparing the 3-phenylisoxazoline-5-carboxamide compound comprises the following steps:

[0035] The compound shown in general formula II is reacted with the compound shown in general formula III or its salt (such as hydrochloride) to obtain the compound shown in general formula I, and the reaction equation is as follows:

[0036] wherein M represents OH or halogen, and the definitions of substituents R1, R2, R3, R4, R5, X, Y, Z1, Z2 and Z3 are as described above.

[0037] In one specific embodiment, the reaction is carried out in the presence of a solvent.

[0038] In another specific embodiment, a base and / or a condensing agent are added during the reaction.

[0039] In one specific embodiment, the base is selected from at least one of inorganic bases (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KHCO3, KF, CsF, KI, NaI, K3PO4, K2HPO4, NaOH, KOH, NaH, KH, etc.) or organic bases (such as DMAP, pyrazole, triethylamine, DIEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, etc.).

[0040] In one embodiment, the condensing agent is at least one selected from the group consisting of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU.

[0041] In one embodiment, the solvent is at least one selected from the group consisting of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran or ethyl acetate.

[0042] In addition, the compound of the present application can be prepared according to the method shown in CN201280017007.3 and the like.

[0043] A herbicidal composition comprising a herbicidally effective amount of at least one of the 3-phenylisoxazoline-5-carboxamide compounds; preferably, further comprising a formulation adjuvant; more preferably, further comprising other active ingredients.

[0044] A method for controlling weeds, comprising applying a herbicidally effective amount of at least one of the 3-phenylisoxazoline-5-carboxamide compounds or the herbicidal composition to plants or to an area of weeds.

[0045] Use of at least one of the 3-phenylisoxazoline-5-carboxamide compounds or the herbicidal composition for controlling weeds, preferably, use of the 3-phenylisoxazoline-5-carboxamide compounds for controlling weeds in useful crops, which are genetically modified crops or crops treated by genome editing technology.

[0046] The compounds of the formula I of the present application have outstanding herbicidal activity against many economically important monocotyledonous and dicotyledonous harmful plants. The active substances of the present application are also effective against perennial weeds which grow from rhizomes, rootstocks or other perennial organs and are difficult to control. In this connection, it is generally immaterial whether the substances are used before sowing, before germination or after germination. Particular mention comes to representatives of the group of monocotyledonous and dicotyledonous weeds which can be controlled by the compounds of the present application without limitation to the specified species. Examples of weed species against which the active substances are effective include the following monocotyledons: annuals of the genera Avena, Secale, Phalaris, Alopecurus, Setaria, Echinochloa, Digitaria, Cynodon and Cyperus, and the perennials of the genera Agropyron, Cynodon, Imperata and Sorghum, and also the perennials of the genus Cyperus.

[0047] With regard to dicotyledonous weed species, the action can extend to species such as annual Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Raphanus, Ipomoea, Sida, Matricaria and Abutilon, and perennial weeds of the genera Convolvulus, Cirsium, Rumex and Artemisia. The active substances according to the application control harmful plants, for example Echinochloa, Sagittaria, Alisma, Alocasia and Glyceria, effectively in the case of the as yet undefined conditions of rice sowing. If the compounds according to the application are applied to the surface of the soil before germination, the seedlings of the weeds can be prevented completely from growing before the weeds have emerged, or growth is stopped at the cotyledon stage, and finally the plants die completely after three to four weeks. The compounds according to the application are particularly active against the following plants, Apera, Lamium, Polygonum, Stellaria, Clematis, Veronica, Viola and Amaranthus, Galium and Kochia.

[0048] Although the compounds according to the application have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they have no or only negligible damage to important economic crop plants, for example wheat, barley, rye, rice, maize, sugar beet, cotton and soybean. In particular, there is very good compatibility with cereal crops, for example wheat, barley and maize, in particular wheat. The compounds according to the application are therefore very suitable for the selective control of unwanted plants in crops of useful plants or ornamentals.

[0049] Due to their herbicidal properties, the active substances can be used for controlling harmful plants in genetically engineered plants which are known or will be known in the future. Genetically engineered plants typically have superior properties, for example resistance to particular pesticides, in particular to particular herbicides, resistance to plant diseases or to disease-causing microorganisms of plant diseases, for example particular insects or fungi, bacteria or viruses. Other particular properties relate to the quantity, quality, storage stability, composition and particular ingredients of the products. Thus, genetically engineered plant products are known which have an increased starch content or an improved starch quality or a different fatty acid composition.

[0050] The compounds of the formula I according to the application or their salts are preferably used in the cultivation of genetically engineered crop plants and ornamentals which are of economic importance, for example cereals, for example wheat, barley, rye, oats, millet, rice, cassava and maize, or in the cultivation of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetable plants. The compounds of the formula I are preferably used as herbicides in the cultivation of useful plants which are resistant to or have been rendered resistant by genetic engineering to the harmful effects of herbicides.

[0051] Traditional breeding of plants with improved properties over known plants includes, for example, traditional crossbreeding and breeding of mutants. In other words, new plants with improved properties can be obtained by means of genetic engineering (cf., for example, EP-0221044 A, EP-0131624 A). Several methods have been described, for example:

[0052] - for improving starch synthesis in plants, genetic engineering is used to alter crop plants (for example WO 92 / 11376, WO 92 / 14827, WO 91 / 19806);

[0053] - transgenic crop plants which are resistant to specific herbicides, for example to the herbicide glufosinate ammonium (EP-0242236 A, EP-0242246 A) or to the herbicides of the glyphosate type (WO 92 / 00377) or to the herbicides of the sulfonylurea type (EP-0257993 A, US-5013659 A);

[0054] - transgenic crop plants, for example of cotton, which are capable of producing the toxin of Bacillus thuringiensis (Bt toxin), which protects the plants from the attack of specific pests (EP-0142924 A, EP-0193259 A);

[0055] - transgenic crop plants with improved fatty acid composition (WO 91 / 13972).

[0056] Numerous molecular biological techniques are known which make it possible to prepare transgenic plants with improved properties (cf., for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, Second Edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, Second Edition 1996 or Christou, Trends in Plant Science 1 (1996) 423-431)). In order to carry out genetic engineering, it is possible to introduce nucleic acid molecules into plasmids, to mutate or to change sequences by recombination of DNA sequences. Using the standard methods described above, it is possible, for example, to exchange substrates, to remove partial sequences or to add natural or synthetic sequences. In order to join DNA fragments to one another, it is possible to attach linkers or adaptors to the fragments.

[0057] Plants cells which produce a gene product with reduced activity can be prepared, for example, by expressing at least one suitable antisense-RNA, sense-RNA for the effect of co-suppression, or by expressing at least one suitably constructed ribozyme which specifically cleaves the transcript of the gene product in question.

[0058] For this purpose it is possible to use DNA molecules which comprise the entire coding sequence of the gene product, including any flanking sequences which can be present, and DNA molecules which comprise only a part of the coding sequence, these parts having to be sufficiently long to achieve an antisense effect in the cell. It is also possible to use sequences which have a high degree of homology with the coding sequence of the gene product but are not identical.

[0059] When the nucleic acid molecule is expressed in plants, the synthesized protein can be localized in any desired plant cell compartment. However, in order to be localized in a particular compartment it is possible, for example, to link the coding region and the DNA sequence to ensure localization in a particular location. These sequences are known to the person skilled in the art (cf., for example, Braun et al., EMBO J. 11 (1992) 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 65 (1988), 846-850; Sonnewald et al. Plant J. 1 (1991), 95-106).

[0060] Using known techniques it is possible to recombine the transgenic plant cells into whole plants. The transgenic plants can be any desired plant species, i.e. monocotyledonous and dicotyledonous plants. In this way it is possible to obtain transgenic plants with improved properties by overexpression, inhibition or suppression of homologous (= natural) genes or gene sequences, or by expression of heterologous (= foreign) genes or gene sequences.

[0061] When the active substances according to the application are used on transgenic crops, in addition to the effect observed on other crops of inhibiting harmful plants, there is often a special effect on the corresponding transgenic crop, for example the spectrum of weed control can be improved or extended, the application rate can be improved, preferably the combination of the resistance of the transgenic crop and the properties of the herbicide are very good, and the growth and yield of the transgenic crop plant are influenced. The use of the compounds according to the application as herbicides for controlling harmful plants in transgenic crop plants is therefore also provided.

[0062] In addition the compounds according to the application can significantly influence the growth of the crop plants. By influencing the metabolism of the plants, using these compounds it is possible to direct the components of the plants and to promote the harvest, for example to dry and dwarf the plants. Furthermore they are suitable for regulating and inhibiting the growth of undesired plants without destroying the growth of the crop. Inhibition of the growth of the plants plays a very important role in many monocotyledonous and dicotyledonous crop plants, since in this way it is possible to reduce or completely prevent lodging.

[0063] The compounds of the present application can be applied using the usual formulations, using wettable powders, emulsifiable concentrates, sprayable solutions, powders or granules. The present application thus also provides herbicidal compositions comprising a compound of formula I. The compounds of formula I can be formulated in various ways depending on the usual biological and / or chemical-physical parameters. Examples of suitable formulation types are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates (SL), emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil dispersions, sprayable solutions, suspension concentrates (SC), dispersible oil suspensions (OD), suspensions in oil or water, solutions of miscible oils, dusts (DP), capsule suspensions (CS), seed dressing compositions, granules for broadcasting and for soil application, injection granules, coating granules and absorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV (ultra-low-volume) formulations, microencapsulations and waxes. These individual formulation types are known and are described, for example, in Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd edition 1979, G. Goodwin Ltd. London.

[0064] The necessary formulation adjuvants, such as inert substances, surfactants, solvents and other additives, are likewise known and are described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd edition, Darland Books Caldwell N.J.; H. v. 01phen, "An Introduction to Clay Colloid Chemistry", 2nd edition, J. Wiley and Sons, N.Y.; C. Marsden, "Solvents Guide", 2nd edition, Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual Wap", MC Publishing Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., N.Y. 1964; ​[Oxirane adduct surfactants], Wiss. Verlagsgesell. Stuttgart 1976; "Chemische Technologie" [Chemical Technology], Vol. 7, C. Hauser Verlag Munich, 4th edition 1986 by Winnacker-Kϋchler.

[0065] Wettable powders are capable of being dispersed in water to give homogeneous suspensions, and comprise, in addition to the active substance, diluents or inert substances, ionic and non-ionic surfactants (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyoxyethyl fatty amines, fatty alcohol polyglycol ether sulphates, alkyl sulphonates, alkylphenyl sulphonates, sodium lignosulphonate, sodium 2,2'-dinaphthylmethane-6,6'-disulphonate, sodium dibutylnaphthalene sulphonate or sodium oleylmethyltauride. To prepare wettable powders, the active substances of the herbicides are finely ground, for example using customary apparatuses, such as hammer mills, fan mills and jet mills, and the adjuvants are mixed in simultaneously or sequentially.

[0066] Concentrated emulsions are prepared by dissolving the active substance in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatic or hydrocarbon compounds or mixtures of solvents, and adding one or more ionic and / or non-ionic surfactants (emulsifiers). Examples of emulsifiers which can be used are, for example, calcium alkylaryl sulphonates, such as calcium dodecylbenzenesulphonate, or non-ionic 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 esters.

[0067] Powders are obtained by grinding the active substance with finely divided solid substances, such as talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspensions, based on water or oil, can be prepared by wet grinding, for example using commercially customary bead mills, with or without the addition of surfactants of another type of formulation as described above.

[0068] Emulsions, such as oil-in-water emulsions (EW), can be prepared using aqueous organic solvents, using stirrers, colloid mills and / or static mixers, if desired, with the addition of surfactants of another type of formulation as described above.

[0069] Granules are prepared by spraying the active material onto an adsorptive material, granulating with inert material, or by concentrating the active material onto the surface of a carrier such as sand, kaolin, granulating with an inert material by means of a binder such as polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable active materials can be granulated using methods known for the preparation of granules for fertilizers, if desired in admixture with fertilizers. Water-suspension granules are prepared using customary methods such as spray-drying, fluidized-bed granulation, pan granulation, mixing using a high-speed mixer and extrusion without solid inert material.

[0070] For the preparation of granules using pan, fluidized-bed, extruder and spray methods, reference is made to the processes described, for example, in the "Spray Drying Manual", 3rd Edition 1979, G. Goodwin Ltd., London; J. E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook", 5th Edition, McGraw-Hill, New York 1973, pages 8-57. For information on the formulation of crop protection products, reference is made to, for example, G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York 1961, pages 181-96 and J. D. Freyer, S. A. Evans "Weed Control Handbook", 5th Edition, Blackwell Scientific Publications, Oxford 1968, pages 101-103.

[0071] The agrochemical formulations usually contain 0.1 to 99 %, in particular 0.1 to 95 %, by weight, of the active substance of the formula I. The concentration of the active substance in wettable powders is, for example, from about 10 to 99 %, the remainder to 100 % by weight consisting of customary formulation components. The concentration of the active substance in emulsifiable concentrates can be from about 1 to 90 %, preferably from 5 to 80 %, by weight. Dustable powders contain from 1 to 30 %, usually preferably from 5 to 20 %, by weight, of the active substance, whereas sprayable solutions contain from about 0.05 to 80 %, preferably from 2 to 50 %, by weight, of the active substance. The content of active substance in water-suspension granules depends mainly on whether the active substance is liquid or solid and on the auxiliaries, fillers, etc. used in the granulation. The content of active substance in water-suspension granules is, for example, between 1 and 95 %, preferably between 10 and 80 %, by weight.

[0072] The formulations described additionally can comprise tackifiers, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and, in general, pH and viscosity regulators which are customary in each case.

[0073] On the basis of these formulations, it is also possible to mix with other pesticidally active substances, such as insecticides, acaricides, herbicides and fungicides, but also with safeners, fertilizers and / or plant growth regulators, either in the form of ready-to-use mixtures or in the form of tank mixes.

[0074] In tank mix or in tank mix formulations, suitable active substances which can be mixed with the active substances according to the application are, for example, the known substances from "The Pesticide Manual", 15thEdn, 2010, The British Crop Protection Council, London, and the literature cited therein. For example, the following herbicidal active substances mentioned below can be mixed with the mixtures of formula I: acetochlor, alachlor, butachlor, propisochlor, prodiamine, S- prodiamine, propachlor, dimethachlor, clacyfos, dichlorprop, dichlorprop-P, fenoxaprop-P, fluazifop-P, haloxyfop-P, propaquizafop, quizalofop-P, quizalofop-P- t-butyl, quizalofop-P- t-propyl, allidochlor, R- allidochlor, propanil, benzoylprop-ethyl, bifenox, clomazone, dimethazone, dimethenamid, flufenazone, mefenacet, metamifop, heptoxdiam, isocarbamid, oxadiargyl, propaquizafop, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P- methyl, dichlorprop-P-ethyl, dichlorprop-P-methyl, dichlorprop-P-ethyl, dichlorprop-P-Sapro- leine, Fluometuron, Benzthiazuron, Methabenzthiazuron, Bensulide, Thiaza- furon, Triazifluron, Tebutam, Clofuron, Methyldymron, Profoxydim, Dymron, Methoxy- prop, Greenall, Monuron, Cybutryne, Fluothiuron, Siduron, Triflu- ron, Esprocarb, Espro- carb-ethyl, EPTC, Bentazon, Dimethamethryn, Dimethamethryn-ethyl, Bifenox, Aciflu- ceton, Benfluralin, Butachlor, Propanil, Chlorprocarb, Fenasulam, BCPC, CPPC, Car- basulam, Butachlor, Propanil, Alachlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met- olachlor, Sulfentrazone, Acetochlor, Metolachlor, Sulfentrazone, Acetochlor, Met-benzofluor, benzofluor-sodium, benzoic acid, benzoylprop-ethyl, benzthiazuron, benzofuracarb, benzofuracarb-sodium, benzyl, benzyl-sodium, benzyl-ubh, benzylubacarcin, benzylubacarcin-sodium, benzylubacarcin-ubh, benzylubacarcin-ubh-509, benzylubacarcin-ubh-ubh, benzylubacarcin-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-509, benzylubacarcin-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh-ubh, benzylubacarcin-ubh-ubh-ubh-ubh-ubD489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOW CO 535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

[0075] When used, commercially available formulations are diluted, if necessary, in the usual manner, for example with water in the case of wettable powders, emulsifiable concentrates, suspensions and granules which are suspended in water. Powders, granules for soil application or solutions for spreading and spraying generally do not require further dilution with inert substances before use. The amount of active compound of formula I required depends on the external conditions, for example temperature, humidity, the nature of the herbicide used and so on. It can vary within wide limits, for example between 0.001 and 1.0 kg a.i. / ha, or more of active substance, but is preferably between 0.005 and 750 g a.i. / ha, in particular between 0.005 and 250 g a.i. / ha. DETAILED DESCRIPTION

[0076] The following examples are intended to illustrate the present application and should not be construed as limiting the application in any way. The scope of the patent protection sought for the present application is defined by the claims.

[0077] In view of the economy and diversity of the compounds, we have synthesized a number of compounds, among which some are selected and listed in Table 1 below. The structures of the specific compounds and the corresponding compound information are shown in Table 1-2. The compounds in Table 1 are only for better illustration of the present application, but do not limit the present application, and for those skilled in the art, this should not be understood as limiting the scope of the above-mentioned subject matter of the present application to the following compounds.

[0078] Table 1 Compound Structure

[0079] Table 2 Compounds 1 H NMR

[0080] Table A and Table B are constructed in the same manner as Table 1 above, except that the general formula I is replaced by the general formula I' having a chiral center wherein, in Table A, the entries under the column heading "Seq. No." are recited in order as 1(S)-168(S). For example, 1(S) corresponds to compound 1 in Table 1 having the S configuration at the chiral carbon in the * position of the general formula. In Table B, the entries under the column heading "Seq. No." are recited in order as 1(R)-168(R). For example, 1(R) corresponds to compound 1 in Table 1 having the R configuration at the chiral carbon in the * position of the general formula.

[0081] Several methods for preparing the compounds of the present application are illustrated in the following Schemes and Examples. Starting materials can be obtained from commercial sources or made by known literature methods or as illustrated. Those skilled in the art will appreciate that other synthetic routes can be used to synthesize the compounds of the present application. Although specific starting materials and conditions are depicted in the schemes and discussed below, other starting materials and conditions can readily be found by those skilled in the art and are encompassed within the scope of the present application. Further, the synthetic methods described below can be further modified to produce additional compounds of the application.

[0082] The following method examples are provided to further illustrate the methods of preparing the compounds of the present application, and the specific materials, amounts and conditions are not intended to limit the scope of the application. The reagents used in the synthesis of the compounds shown in the following tables are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0083] Representative compounds are synthesized as follows, and other compounds are synthesized in a similar manner.

[0084] 1. Synthesis of compound 24

[0085] Into a 100 mL round bottom flask, 24-1 (0.20 g, 1.0 eq), methoxymethylamine hydrochloride (0.065 g, 1.0 eq), EDCI (0.23 g, 1.5 eq), HOBT (0.160 g, 1.5 eq), triethylamine (0.237 g, 3 eq), 10 mL DCM were added and the reaction was allowed to proceed at room temperature overnight. After the reaction was completed, silica gel powder was added to the reaction mixture and the mixture was purified by column chromatography. The solvent was removed by rotary evaporation to give compound 24 as a white solid (0.2 g, 96% purity, 84% yield).

[0086] 2. Synthesis of compound 28

[0087] Take a 100 mL round-bottom flask, add 28-1 (0.180 g, 1.0 eq), methoxymethylamine hydrochloride (0.061 g, 1.0 eq), EDCI (0.186 g, 1.5 eq), HOBT (0.128 g, 1.5 eq), triethylamine (0.189 g, 3 eq), 10 mL DCM into the flask, and react at room temperature overnight. After the reaction is completed, add silica gel powder to the sample, purify by column, and spin dry to obtain white solid 28 (0.058 g, purity 96%, yield 27%).

[0088] 3. Synthesis of compound 140(S)

[0089] (1) Compound 140-1 (150 mg, 0.58 mmol) was dissolved in 4 ml of dichloromethane, and oxalyl chloride (0.2 mL, 1.59 mmol) and a catalytic amount of N,N-dimethylformamide were added under ice water bath, and the reaction was carried out at room temperature for 2 h, and LCMS was used to monitor the completion of the reaction. The reaction liquid was concentrated to obtain 140-2 crude product for use; compound 140-3 (150 mg) was taken, 3 ml of DCM was added, triethylamine (235 mg, 2.32 mmol) was added, and 140-2 (166 mg, 0.58 mmol) was added dropwise, and the mixture was stirred at room temperature for 0.5 h. LCMS was used to monitor the completion of the reaction. The reaction liquid was diluted with DCM, washed with aqueous ammonium chloride solution, dried and concentrated, and the residue was purified by column chromatography to obtain compound 140-4 (200 mg, yield 90%, white oil).

[0090] (2) In a 50 mL single-neck flask, 140-4 (0.2 g, 0.52 mmol) was dissolved in 3 ml of DMF, potassium carbonate (0.22 g, 1.59 mmol) and iodomethane (0.38 g, 2.65 mmol) were added, and the mixture was stirred at room temperature for 1 h. LCMS was used to monitor the completion of the reaction. The reaction liquid was diluted with EA, washed with half-saturated aqueous sodium chloride solution, dried and concentrated, and the residue was purified by column chromatography to obtain compound 140(S) (105 mg, yield 50%, white oil).

[0091] Biological activity evaluation:

[0092] The activity level criteria for plant destruction (i.e., growth control rate) are as follows:

[0093] 9: complete death;

[0094] 8: growth control rate greater than or equal to 90% and less than 100%;

[0095] 7: growth control rate greater than or equal to 80% and less than 90%;

[0096] Grade 6: growth control rate is greater than or equal to 70% and less than 80%;

[0097] Grade 5: growth control rate is greater than or equal to 50% and less than 70%;

[0098] Grade 4: growth control rate is greater than or equal to 30% and less than 50%;

[0099] Grade 3: growth control rate is greater than or equal to 20% and less than 30%;

[0100] Grade 2: growth control rate is greater than or equal to 10% and less than 20%;

[0101] Grade 1: growth control rate is less than 10%;

[0102] Grade 0: no effect.

[0103] The above growth control rate is fresh weight control rate.

[0104] Post-emergence test experiment:

[0105] The seeds of monocotyledonous and dicotyledonous weeds and the seeds of main crops are placed in plastic pots with soil, and then covered with 0.5-2 cm soil, and the test plants are treated 2 weeks after sowing at the 2-3 leaf stage. The test compounds of the present application are dissolved in acetone, and then Tween 80 is added, and 1.5 liters / ha of methyl oleate emulsion is used as an adjuvant, and a certain concentration of solution is diluted with water, and sprayed on the plants with a spray tower. After application, the test plants are cultured in the greenhouse for 3 weeks, and the test results of weeds are counted. Representative data are shown in Table 3.

[0106] Table 3 Post-emergence weed test results

[0107] Pre-emergence test experiment:

[0108] The seeds of monocotyledonous and dicotyledonous weeds and the seeds of main crops are placed in plastic pots with soil, and then covered with 0.5-2 cm soil, and the test compounds of the present application are dissolved in acetone, and then Tween 80 is added, and a certain concentration of solution is diluted with water, and sprayed immediately after sowing. After application, the test results are observed after 4 weeks of culture in the greenhouse. Representative data are shown in Table 4.

[0109] Table 4 Pre-emergence weed test results Note: N represents no data, and Control Compound A:

[0110] Meanwhile, through many tests, it is found that the compound and the composition thereof can prevent many key grass weeds and broadleaf weeds, and tests on crops and grass lawns under different application modes also show excellent selectivity and commercial value.

[0111] Finally, it should be noted that the above examples are only used to illustrate the technical solutions of the present application and are not limited. Although the present application has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solutions of the present application can be modified or replaced by equivalents without departing from the spirit and scope of the present application.

Claims

1. A 3-phenylisoxazoline-5-carboxamide compound or a salt thereof, as shown in the general formula I: in, X is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, or arylalkyl; Y is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, -(CO)OR, -(CO)R, aryl, or heterocyclyl; wherein the alkyl, alkenyl, or alkynyl group is optionally substituted with at least one group selected from halogen, cyano, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, -OR, -SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, or -(CO)N(R)(OR); Z1, Z2, and Z3 independently represent hydrogen, halogen, or alkyl; R1, R2, R3, R4, and R5 each independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -(CO)R, -(CO)N(R)2, -alkylene-OR, -alkylene-SR, -alkylene-SOR, -alkylene-(SO2)R, -alkylene-N(R)2, -alkylene-(CO)R, -alkylene-(CO)N(R)2, cyano, nitro, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, heterocyclyl, arylalkyl, or heterocyclylalkyl; The aforementioned cycloalkyl, cycloalkenyl, aryl or heterocyclic group is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR, -SR, -alkylene-OR, -alkylene-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -SOR, -S02R, -OS02R or -N(R)2; R each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted by at least one group selected from halogen, hydroxy, alkoxy, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. A 3-phenylisoxazoline-5-carboxamide compound or a salt thereof according to claim 1, characterized in that: X is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, heterocyclyl, heterocyclylC1-C8 alkyl, aryl, or arylC1-C8 alkyl; Y is hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, -(CO)OR, -(CO)R, aryl, or heterocyclyl; wherein C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is optionally substituted with at least one group selected from halogen, cyano, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclyl, aryl, -OR, -SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, or -(CO)N(R)(OR); Z1, Z2, and Z3 independently represent hydrogen, halogen, or C1-C8 alkyl; R1, R2, R3, R4, and R5 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -(CO)R, -(CO)N(R)2, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -(C1-C8 alkylene)-SOR, -(C1-C8 alkylene)-(SO2)R, -(C1-C8 C8 alkylene)-N(R)2, -(C1-C8 alkylene)-(CO)R, -(C1-C8 alkylene)-(CO)N(R)2, cyano, nitro, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, aryl, heterocyclyl, arylC1-C8 alkyl or heterocyclylC1-C8 alkyl; The aforementioned C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclic group is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, -OR, -SR, -(C1-C8 alkylene)-OR, -(C1-C8 alkylene)-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -SOR, -S02R, -OS02R or -N(R)2; R each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted by at least one group selected from halogen, hydroxy, C1-C8 alkoxy, cyano or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-substituted C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo-substituted C1-C8 alkoxy.

3. A 3-phenylisoxazoline-5-carboxamide compound or a salt thereof according to claim 1 or 2, characterized in that: X is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, heterocyclyl, heterocyclylC1-C6 alkyl, aryl or arylC1-C6 alkyl; Y is hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, -(CO)OR, -(CO)R, aryl, or heterocyclyl; wherein C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is optionally substituted with at least one group selected from halogen, cyano, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclyl, aryl, -OR, -SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, or -(CO)N(R)(OR); Z1, Z2, and Z3 independently represent hydrogen, halogen, or C1-C6 alkyl; R1, R2, R3, R4, and R5 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -(CO)R, -(CO)N(R)2, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, -(C1-C6 alkylene)-SOR, -(C1-C6 alkylene)-(SO2)R, -(C1-C6 alkylene) C6 alkylene)-N(R)2, -(C1-C6 alkylene)-(CO)R, -(C1-C6 alkylene)-(CO)N(R)2, cyano, nitro, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, haloC1-C6 alkyl, haloC2-C6 alkenyl, haloC2-C6 alkynyl, aryl, heterocyclyl, arylC1-C6 alkyl or heterocyclylC1-C6 alkyl; The aforementioned C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl or heterocyclic group is optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, -OR, -SR, -(C1-C6 alkylene)-OR, -(C1-C6 alkylene)-SR, -O(CO)R, -(CO)R, -(CO)OR, -(CO)N(R)2, -SOR, -S02R, -OS02R or -N(R)2; R each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted by at least one group selected from halogen, hydroxy, C1-C6 alkoxy, cyano or C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-substituted C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-substituted C1-C6 alkoxy; Preferably, the compound is selected from any one of Table 1 and Table AB.

4. A 3-phenylisoxazoline-5-carboxamide compound having a chiral center as shown in Formula I': in, The carbon atom at position * is a chiral center, and the substituents Z1, Z2, Z3, R1, R2, R3, R4, R5, X and Y are defined as in any one of claims 1 to 3; Based on the content of stereoisomers with R and S configurations at position *, it has a stereochemical purity of 60-100% (S), preferably 70-100%, more preferably 80-100%, further preferably 90-100%, and even more preferably 95-100%; or based on the content of stereoisomers with R and S configurations at position *, it has a stereochemical purity of 60-100% (R), preferably 70-100%, more preferably 80-100%, further preferably 90-100%, and even more preferably 95-100%.

5. A method for preparing a 3-phenylisoxazoline-5-carboxamide compound or a salt thereof according to any one of claims 1 to 4, characterized in that: The following steps are involved: The compound represented by general formula II is reacted with the compound represented by general formula III or a salt thereof to obtain the compound represented by general formula I, and the reaction equation is as follows: wherein M represents OH or halogen, and the substituents R1, R2, R3, R4, R5, X, Y, Z1, Z2 and Z3 are as defined in any one of claims 1 to 4; Preferably, the reaction is carried out in the presence of a solvent; more preferably, a base and / or a condensing agent is added during the reaction; further preferably, the base is selected from at least one of an inorganic base or an organic base; the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU; and / or the solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, tetrahydrofuran or ethyl acetate.

6. A herbicide composition, characterized in that The invention comprises a herbicidally effective amount of at least one of the 3-phenylisoxazoline-5-carboxamide compounds or salts thereof according to any one of claims 1 to 4; preferably, further comprises a formulation adjuvant; more preferably, further comprises other active ingredients.

7. A method for controlling weeds, characterized in that: The method comprises applying a herbicidally effective amount of at least one of the 3-phenylisoxazoline-5-carboxamide compounds or salts thereof according to any one of claims 1 to 4 or the herbicide composition according to claim 6 on plants or weedy areas.

8. Use of at least one of the 3-phenylisoxazoline-5-carboxamide compounds or salts thereof according to any one of claims 1 to 4, or the herbicide composition according to claim 6, for controlling weeds. Preferably, the 3-phenylisoxazoline-5-carboxamide compound or salt thereof is used to control weeds in useful crops, which are transgenic crops or crops treated with genome editing technology.

Images