Substituted heterocyclic compound and preparation method therefor, herbicidal composition and use thereof

Abstract

The present invention relates to the technical field of pesticides, and particularly to a substituted heterocyclic compound and a preparation method therefor, a herbicidal composition and a use thereof. The compound is represented by general formula (I), wherein Q1, Q2, and Q3 each independently represent N or CR5; X represents aryl or heteroaryl; Y represents hydrogen, -OY1, -(CO)OY2, -(CO)SY2, or -(CO)N(Y2)2; and R1, R2, R3, R4, and R5 each independently represent hydrogen, halogen, cyano, nitro, etc. The compound has excellent herbicidal activity and crop safety.

Description

Substituted heterocyclic 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 substituted heterocyclic 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 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 substituted heterocyclic compound, a preparation method thereof, a herbicidal composition and application. The compound has excellent herbicidal activity and crop safety.

[0004] The technical solutions adopted by the present application are as follows:

[0005] A substituted heterocyclic compound or a salt thereof as shown in general formula I:

[0006] Q1, Q2 and Q3 independently represent N or CR5;

[0007] X represents aryl or heteroaryl;

[0008] Y represents hydrogen, -OY1, -(CO)OY2, -(CO)SY2 or -(CO)N(Y2)2;

[0009] Y1 represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, -(CO)R 21 or -(CO)OR 21 , the alkyl, alkenyl or alkynyl is optionally substituted with at least one group selected from halogen, cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2;

[0010] Y2 independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl, the alkyl, alkenyl or alkynyl is optionally substituted with at least one group selected from halogen, cycloalkyl, aryl, heterocyclyl, -OR 21, -S(O) 21 , -S(O) n R 21 or -N(R 21 )2, at least one of the groups R

[0011] R1, R2, R3, R4, R5, independently, represent hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -(CO)N(R 21 )2, -S(O) n R 21 or -N(R 21 )2, the alkyl, alkenyl or alkynyl group being optionally substituted by at least one group selected from halogen, cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2;

[0012] n is 0, 1 or 2;

[0013] R 21 , independently, represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, the alkyl, alkenyl or alkynyl group being optionally substituted by at least one group selected from halogen or alkoxy;

[0014] the preceding cycloalkyl, heterocyclyl, aryl or heteroaryl group being optionally substituted by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -O(CO)R 10 , -(CO)N(R 10 )2, -(CS)N(R 10 )2, -(SO)R 10 or -(SO2)R 10 ;

[0015] R 10 , independently, are hydrogen, alkyl, haloalkyl, aryl or heterocyclyl, unsubstituted or substituted by at least one group selected from halogen, alkyl;

[0016] the following compounds are excluded:

[0017] In a particular embodiment, Y1represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, aryl, heterocyclyl, -(CO)R 21 or -(CO)OR 21 , said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one radical chosen from halogen, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2;

[0018] Y2represents independently for each occurrence hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, aryl or heterocyclyl, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one radical chosen from halogen, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2;

[0019] R1, R2, R3, R4, R5represent independently for each occurrence hydrogen, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -(CO)N(R 21 )2, -S(O) n R 21 or -N(R 21 )2, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one radical chosen from halogen, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2;

[0020] n is 0, 1 or 2;

[0021] R 21each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, arylC1-C8alkyl, heterocyclyl or heterocyclylC1-C8alkyl, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one group selected from halogen or C1-C8alkoxy;

[0022] each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, arylC1-C8alkyl, heterocyclyl or heterocyclylC1-C8alkyl, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one group selected from halogen or C1-C8alkoxy; 10 10 10 10 10 10 10 10 10 each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, arylC1-C8alkyl, heterocyclyl or heterocyclylC1-C8alkyl, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one group selected from halogen or C1-C8alkoxy;

[0023] R 10 each independently is hydrogen, C1-C8alkyl, halogenated C1-C8alkyl, aryl or heterocyclyl, unsubstituted or substituted by at least one group selected from halogen, C1-C8alkyl.

[0024] In another particular embodiment, Y1represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, aryl, heterocyclyl, -(CO)R 21 or -(CO)OR 21 , said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl being optionally substituted by at least one group selected from halogen, C3-C6cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2;

[0025] Y2each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, aryl or heterocyclyl, said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl being optionally substituted by at least one group selected from halogen, C3-C6cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR​​​​​​​​21 -S(O) n R 21 or -N(R 21 )2;

[0026] R1, R2, R3, R4, R5, independently, represent hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -(CO)N(R 21 )2, -S(O) n R 21 or -N(R 21 )2, said C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl being optionally substituted by at least one group selected from halogen, C3-C6 cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2;

[0027] n is 0, 1 or 2;

[0028] R 21 , independently, represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclyl or heterocyclyl C1-C6 alkyl, said C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl being optionally substituted by at least one group selected from halogen or C1-C6 alkoxy;

[0029] said preceding C3-C6 cycloalkyl, heterocyclyl, aryl or heteroaryl being 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, halo C1-C6 alkyl, halo C2-C6 alkenyl, halo C2-C6 alkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -O(CO)R 10 , -(CO)N(R 10 )2, -(CS)N(R 10 )2, -(SO)R 10 or -(SO2)R 10 ;

[0030] R 10 are independently hydrogen, C1-C6alkyl, haloC1-C6alkyl, aryl or heterocyclyl unsubstituted or substituted with at least one group selected from halo, C1-C6alkyl.

[0031] In another embodiment, Q2and Q3are not both N.

[0032] In the definitions of the compounds of the general formulae described above and in all the formulae below, the professional 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-chained or branched. As in the compound word "cycloalkylalkyl" the alkyl groups can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, and the like. Alkyl groups are, for example, C1alkyl - methyl; C2alkyl - ethyl; C3alkyl - propyl, such as n-propyl or isopropyl; C4alkyl - butyl, such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5alkyl - pentyl, such as n-pentyl; C6alkyl - 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 group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein the double bonds can be in any position. Halo is fluorine, chlorine, bromine or iodine.

[0033] Unless specifically indicated otherwise, "aryl" as used in the present application includes, but is not limited to, phenyl, naphthyl, " Heterocyclyl" as used in the present application includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups " Heterocyclyl" as used in the present application includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups

[0034] The term "optionally" or "optional" means that the subsequently described event or circumstance can or can not occur, and thus that description is inclusive of 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 substituent groups are each selected independently of the others, and can be the same or different. The same applies to ring systems formed from different atoms and units. At the same time, the scope of the claims is to exclude those compounds which are chemically unstable under standard conditions, as known to the person skilled in the art.

[0035] In addition, unless specifically limited otherwise, the term "substituted" as used herein means substituted with one, two, three, four or five groups; groups (including heterocyclyl, aryl, etc.) not marked with a specific attachment position can be attached at any position, including the position attached to C or N; if it is substituted, the substituents can also be substituted at any position, as long as the rules of chemical bond connection are met. For example, a heteroaryl group substituted with 1 methyl group may represent , etc.

[0036] If various functional groups are present, the present application also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0037] Stereoisomers can be obtained from mixtures obtained in the preparation by optical resolution. Stereoisomers can also be prepared selectively by using stereoselective reactions and using optically active starting materials and / or auxiliaries. For optical resolution, it is generally possible to use conventional methods (cf. Textbooks of Stereochemistry), for example the following methods for the resolution of mixtures into diastereomers, for example physical methods such as crystallization, chromatography, in particular column chromatography and high-pressure liquid chromatography, distillation methods, which are optionally carried out under reduced pressure, extraction and other methods, usually with chromatographic separation on chiral stationary phases, which make it possible to separate the residual mixtures of enantiomers. Suitable for preparative amounts or for industrial scale are methods such as crystallization of diastereomeric salts, which can be obtained from the compounds with optically active acids and, if acidic groups are present, with optically active bases, if desired.

[0038] The preparation method of the substituted heterocyclic compounds described above comprises the following steps:

[0039] When Y represents -(CO)OY2, -(CO)SY2or -(CO)N(Y2)2, the compound of formula II is reacted with the compound of formula III to obtain the compound of formula I', as shown in the following reaction equation:

[0040] (Y represents -(CO)OY2, -(CO)SY2or -(CO)N(Y2)2)

[0041] When Y represents OY1, the compound of formula IV or the compound of formula V is reacted with the compound of formula III to obtain the compound of formula I" and then the target compound is obtained through a conventional substitution reaction.

[0042] When Y is hydrogen, it is obtained from the compound of formula I' through a conventional hydrolytic decarboxylation reaction, or from the compound of formula I" through a conventional reduction reaction.

[0043] wherein Hal represents halogen, and the definitions of substituents X, Y, R1, R2, R3, R4, Q1, Q2and Q3are as previously described.

[0044] In one specific embodiment, the reaction for preparing the compound of formula I' or I" is carried out in the presence of a base and a solvent.

[0045] In another specific embodiment, the base is selected from at least one of inorganic bases (such as NaOH, KOH, KF, NaH or KH, etc.) or organic bases (such as n-butyllithium, t-butyllithium, sodium t-butoxide, potassium t-butoxide, etc.).

[0046] In another specific embodiment, the solvent is selected from at least one of toluene, dichloroethane, dimethyl sulfoxide, acetonitrile, ethyl acetate, diethyl ether, hexane or tetrahydrofuran.

[0047] In addition, the compound of the present application can be prepared according to the method shown in WO2023186691A1.

[0048] A herbicidal composition comprising a herbicidally effective amount of at least one of the substituted heterocyclic compounds; preferably, further comprising a formulation adjuvant; more preferably, further comprising other effective ingredients.

[0049] A method for controlling weeds, comprising using a herbicidally effective amount of at least one of the substituted heterocyclic compounds or the herbicidal composition on plants or weed areas.

[0050] The use of at least one of the mentioned substituted heterocyclic compounds or the mentioned herbicidal composition for controlling weeds, preferably for controlling weeds in transgenic crops or crops treated with genome editing technology.

[0051] 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 should be made of the examples of groups 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, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Cynodon and Cyperus, and the perennials of the genera Agropyron, Cynodon, Imperata and Sorghum, and the perennial Cyperus.

[0052] As regards dicotyledonous weed species, the spectrum of action can extend to species such as annuals of the genera Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Raphanus, Ipomoea, Sida, Matricaria and Abutilon, and the perennials of the genera Convolvulus, Cirsium, Rumex and Artemisia. The active substances of the present application are effective in controlling harmful plants under the conditions prevailing at sowing of rice, for example Echinochloa, Sagittaria, Alisma, Alocasia and Cyperus. If the compounds of the present application are applied to the soil surface before germination, the seedlings of the weeds can be completely prevented from growing before the weeds emerge, or growth can be stopped at the stage of the first leaves, and finally the plants can die completely after three to four weeks. The compounds of the present application are particularly well active against the following plants: Apluda, Lamium, Polygonum, Stellaria, Clematis, Veronica, Arabis, Viola and Amaranthus, Galium and Kochia.

[0053] Although the compounds of the present application have outstanding 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 a very good compatibility with cereal crops, for example wheat, barley and maize, in particular wheat. The compounds of the present application are therefore very suitable for the selective control of unwanted plants in crop plants or ornamental plants.

[0054] Due to their herbicidal properties, these active substances can be used for controlling harmful plants in genetically engineered plants which are known or will be developed in the future. Genetically engineered plants usually have superior properties, for example resistance to certain pesticides, in particular to certain herbicides, resistance to plant diseases or to disease-causing microorganisms of plant diseases, for example to certain insects or fungi, bacteria or viruses. Other special properties are associated with the following properties of the products, for example quantity, quality, storage stability, components and specific ingredients. Thus, genetically engineered plant products are known which have an increased starch content or an improved starch quality or a different fatty acid composition.

[0055] The compounds of the formula I or their salts according to the application are preferably used in the cultivation of economically important genetically engineered crops and ornamental plants, for example cereals, such as wheat, barley, rye, oats, millet, rice, cassava and maize, or in the cultivation of sugar beets, cotton, soybeans, rapeseed, potatoes, tomatoes, peas 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 the action of herbicides or which have been rendered resistant to the action of herbicides by genetic engineering.

[0056] Traditional methods for breeding plants with improved properties compared to known plants include, for example, traditional crossbreeding methods and breeding of mutants. In other words, new plants with improved properties can be obtained by means of methods of genetic engineering (cf., for example, EP-0221044 A, EP-0131624 A). For example, several methods have been described:

[0057] - for improving starch synthesis in plants, crop plants are modified by genetic engineering (for example WO 92 / 11376, WO 92 / 14827, WO 91 / 19806);

[0058] - genetically engineered crop plants which are resistant to certain herbicides, for example to herbicides of the class of glufosinate herbicides (for example EP-0242236 A, EP-0242246 A) or to herbicides of the class of glyphosate herbicides (WO 92 / 00377) or to herbicides of the class of sulfonylurea herbicides (EP-0257993 A, US-5013659 A);

[0059] - genetically engineered crop plants, for example of cotton, which are capable of producing toxins of Bacillus thuringiensis (Bt toxins) which protect the plants from the attack of certain pests (EP-0142924 A, EP-0193259 A);

[0060] - genetically engineered crop plants which have an improved fatty acid composition (WO 91 / 13972).

[0061] A number of molecular biological techniques are known which make it possible to produce transgenic plants with improved properties (see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd Edition 1996 or Christou, Trends in Plant Science 1 (1996) 423-431)). In order to achieve the genetic engineering operations, 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.

[0062] It is possible to produce plant cells with reduced activity of a gene product, for example by expressing at least one suitable antisense-RNA, sense-RNA to achieve 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.

[0063] 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 the effect of antisense 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.

[0064] When nucleic acid molecules are expressed in plants, the synthesized proteins 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 (see, 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).

[0065] Using known techniques, it is possible to recombine 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.

[0066] When using the active substances according to the application 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 enlarged, the application rate at the time of application can be improved, the combination of the preferred transgenic crop's resistance and the herbicide's performance is very good, and the growth and yield of the transgenic crop plant is influenced. The use of the compounds according to the application as herbicides for controlling harmful plants in transgenic crop plants is therefore also provided.

[0067] In addition, the compounds according to the application can significantly regulate the growth of crop plants. By regulating the components involved in plant metabolism, the use of these compounds allows targeted control of the plant and promotes harvesting, for example, by drying and dwarfing the growth of the plant. 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 plant plays a very important role in many monocotyledonous and dicotyledonous crops, since it can reduce or completely prevent lodging.

[0068] The compounds according to the application can be applied using the usual formulations, using wettable powders, emulsifiable concentrates, sprayable solutions, powders or granules. The application therefore also provides herbicidal compositions comprising the compounds of the formula I. The compounds of the formula I can be formulated in various ways depending on the usual biological and / or chemical-physical parameters. Suitable examples of formulation types are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates (SL), emulsifiable concentrates (EC), emulsions, for example oil-in-water and water-in-oil (EW), sprayable solutions, suspension concentrates (SC), dispersible oil suspensions (OD), suspensions in oil or water, solutions of miscible oils, powders (DP), capsule suspensions (CS), seed dressing compositions, granules for spreading and soil application, injection granules, coating granules and absorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV (ultra-low-volume) formulations, microencapsulations and wax formulations. These individual formulation types are known and are described, for example, in Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], 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.

[0069] Necessary formulation aids, such as inert substances, surfactants, solvents and other additives are likewise known and are described, for example, in Watkins' "Handbook of Insecticide Dusts and Bait Application", 2nd Ed., Darland Books, Caldwell N.J.; H. v. 01 phen "Einfuhrung in die Kolloidchemie", 2nd Ed., J. Wiley and Sons, N.Y.; C. Marsden "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood N.J.; Sisley and Wood "Encyclopedia of Surfactants", Chemical Publishing Co., N.Y. 1964; [epoxyethane adduct surfactants], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Kuchler "Chemische Technologie", Vol. 7, C. Hauser Verlag Munich, 4th Ed. 1986.

[0070] Wettable powders are capable of dispersing uniformly in water and comprise, in addition to the active substances, 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 auxiliaries are mixed in simultaneously or sequentially.

[0071] Concentrated emulsions are prepared by dissolving the active substances in organic solvents, 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) thereto. 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.

[0072] ​The active substances and finely divided solid substances, such as talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth, are ground to a powder. Suspensions based on water or oil can be prepared by wet grinding, for example, using a commercially available pearl mill, with or without the addition of a surfactant of the other formulation type as described above.

[0073] 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 a surfactant of the other formulation type as described above.

[0074] Granules are prepared by spraying the active substance onto adsorbents, using inert material granulation, or by concentrating the active substance onto the surface of a carrier, such as sand, kaolin, and granulating the inert material by means of a binder, such as polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable active substances can be granulated using the methods used for the preparation of fertilizer granules, if desired, with the addition of fertilizers. Water-soluble granules are prepared using the usual methods, such as spray-drying, fluidized-bed granulation, pan granulation, mixing using a high-speed mixer and extrusion without the addition of solid inert material.

[0075] For the preparation of granules using pan, fluidized-bed, extruder and spray-coating methods, reference is made to the processes described, for example, in the "Handbook of Spray Drying", 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, for example, to 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.

[0076] Agricultural chemical formulations usually contain from 0.1 to 99 %, in particular from 0.1 to 95 %, by weight, of active substance of the formula I. The concentration of active substance in wettable powders is, for example, from about 10 to 99 %, the usual formulation components making up the remainder to 100 % by weight. The concentration of 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 active substance, whereas sprayable solutions contain from about 0.05 to 80 %, preferably from 2 to 50 %, by weight, of active substance. The content of active substance in water-suspension granules is, for example, between 1 and 95 %, preferably between 10 and 80 %, by weight, depending on whether the active substance is liquid or solid and on the auxiliaries, fillers, etc. used during granulation. The content of active substance in water-suspension granules is, for example, between 1 and 95 %, preferably between 10 and 80 %, by weight.

[0077] The formulations mentioned additionally comprise, if appropriate, adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and, in general, pH and viscosity regulators which are customary in each case.

[0078] On the basis of these formulations, it is also possible to mix with other pesticidally active substances, for example insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers and / or plant growth regulators, either as premixes or as tank mixes.

[0079] Suitable active substances that can be mixed with the active substances of the present invention in compound formulations or tank-mixed formulations include, for example, known substances in the "World Encyclopedia of New Pesticide Varieties Technology", China Agricultural Science and Technology Press, 2010.9 and the literature cited herein. For example, the following herbicidal active substances can be mixed with compounds of Formula I (Note: the name of the compound is either the common name according to the International Organization for Standardization (ISO) or the chemical name, with a code where appropriate): acetochlor, butachlor, metolachlor, isopropachlor, isopropachlor, succinyl-metolachlor, propachlor, chlorpyrifos, chlorpyrifos, naphthalenepropanoyl-methyl, R-L-naphthalenepropanoyl-methyl, propargyl, benzylthiamethoxam, bisbenzyl-methyl, pyrifluquinazon, chlorpyrifos, flubutyroxychlor, brobutyroxychlor, dimethoate, high-efficiency dimethoate, ethoxybenzyl-methyl, flubutyroxychlor, methoxythiamethoxam, pyrifluquinazon, isoxachlor, high-efficiency methylparaben, high-efficiency methylparaben. Acetaminophen, clethodim, butyrazosulfuron, cyprochloraz, flusulfuron, heptanosulfuron, isobutyrazosulfuron, propyzamide, terbutyrazosulfuron, methylparaben, metolachlor, methylcyclohexane, chlorpyrifos, propyzamide, pendimethalin, carbaryl, succinylmethrin, tricyclomethrin, butyrazosulfuron, succinylmethrin, bensulfuron-methyl, naphthylmethrin, acetochlor, naphthylmethrin, thiamethoxam, pyrimethanil, bensulfuron-methyl, chlorpyrifos, butyrazosulfuron, flupyrazole, atrazine, simazine, promethazine, cypermethrin, cypermethrin, atrazine, pyrazosulfuron, isopropazine, flumethrin, terbutyraz, terbutyraz, triazine flumethrin, cyprochlorazine, glyphosate, chlorpyrifos Phosphatidylcholine, Simazine, Ziziphus jujuba, Dichlorvos, Isoamyl acetate, Cyprodinil, Atrazine, Butyraz, Butyraz, Terbutaline, Methoxypropazine, Cypermethrin, Herbicides, Clonazine, Atrazine, Methoxypropazine, Glycyrrhizin, Cyanobacterium trioxide, Indaziflam, Greensulfuron, Methsulfuron-methyl, Benzylsulfuron, Chlorpyrifos, Bensulfuron-methyl, Thisulfuron-methyl, Pyrimisulfuron-methyl, Methiosulfuron-methyl, Sodium formamide sulfuron, Ethersulfuron-methyl, Etherbensulfuron-methyl, Methsulfuron-methyl, Nicosulfuron-methyl, Aminosulfuron-methyl, Acylsulfuron-methyl, Ethoxysulfuron-methyl, Cyprosulfuron-methyl, Sulfadiazine, Tetraazolidinylsulfuron, Pyrimisulfuron, Monosulfuron-methyl, Fluazolidinylsulfuron, Flupyrimisulfuron, Flupyrimisulfuron, Epimethrin Sulfuric acid, pyrazosulfuron, flusulfuron, propanil, trifluprosulfuron, sulfonylsulfuron, trifluralin, flusulfanil, trifluralin, mesosulfuron sodium salt, flupyrsulfuron, thiosulfuron, pyrimethanil, propyrisulfuron, pyrazosulfuron, trifluralin, flusulfanilamide, quizalofop-p-ethyl, ethoxysulfuron, glufosinate, bensulfuron, chlorfluazuron ethyl, methylfluzoxystrobin, trifluralin, methoxysulfuron, trifluralin, flufenoxuron, flufenoxuron, oxysulfuron, metolachlor, sulfadiazine, flufenoxuron, oxysulfuron, metolachlor, flufenoxuron, flufenoxuron, halosafen, chlormequat chloride, isoproturon, linuron, diuronSaprolegnia, fluroxypyr, bensulfuron, methyl bensulfuron, bensulfuron, sulfothiamethoxam, isoxaflutole, terbutaline, clodinafop-methyl, chlorobromosulfuron, methyl methoxysulfuron, methyl methoxysulfuron, bromosulfuron, methoxysulfuron, chlorpyrifos, metribuzin, cycloroxysulfuron, felsulfuron, flusulfuron, glufosinate, fensulfuron, cyproconazole, thiamethoxam, fensulfuron, chlorpyrifos, methamidophos, thiamethoxam, trimethourea, oxazolium, Monisouron, Anisuron, Methiuron, Chloreturon, tetraflufenozide, betaine, betaine-ethyl, betaine, sulfonamide, terbutaline, fensulfuron-methyl, fensulfuron-methyl, fensulfuron-methyl, fensulfuron-methyl, chlorpyrifos, carboxazo le, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, Butyrazosulfan, Clethodim, Metrazine, Clethodim, Wild Grass, Permethrin, Clethodim, Barnyardgrass, Cypermethrin, Oat Grass, Dimethoate, Ethylmethazine, Methiobencarb, Clethodim, Benzoate, Methiobencarb, Thionylmethazine, Methiobencarb, 2,4-D Butyl Acetate, 2,4-D Sodium Chloride, 2,4-D Isooctyl Acetate, 2,4-D Sodium Salt, 2,4-D Dimethylamine Salt, 2,4-D Chlorethyl Thiate, 2,4-D Chloride, 2,4-D Propionic Acid, High 2,4-D Propionate, 2,4-D Butyric Acid, 2,4-D Chlorpropionic Acid, 2,4-D Propionate 2,4,5-chlorobutyric acid, 2,4,5-propylpropionic acid, 2,4,5-propylbutyric acid, 2,4,5-chloromethacin, MCPA, dicamba, quizalofop-p-ethyl, cyhalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, cyhalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl, quizalofop-p-ethyl In, proponitrophenol, glyphosate, barnyardphos, glufosinate, methyl parathion, glyphosate, piperazine, diammonium phosphate, dimethoate, phosmet, fenpropathrin, fenpropathrin, fenpropathrin, dimethoate, fenpropathrin, imidacloprid, imidacloprid acetic acid, imidacloprid quinolinic acid, methoxymethylene, methoxymethylene ammonium salt, imidacloprid acetic acid, imidacloprid, clopyralid, clopyralid isooctyl ester, dichloropyridine acid, aminopyridine acid, trichloropyridine acid, fluthion, haloxypyridine, trichloropyridine phenol, thiamethoxam, flupyridine, clopyralid, flupyridine hydrazone, trichloropyridine butoxyethyl ester, cliodinate, clethodim, thiamethoxam, quizalofop-p-ethyl, cyclobenzanone, butenazine, oxadiazine, pyranazine, buthidazole, cyproconazoleAmetridione, Amibuzin, bromobenzonitrile, octanoyl bromobenzonitrile, octanoyl iodobenzonitrile, iodobenzonitrile, diphenylacetonitrile, bispyribac-sodium, hydroxybispyribac-sodium, Iodobonil, pyrimisulfuron-methyl, diflubenzuron, penoxsulam, sulfadiazine, chlorpyrifos-sulfuron-methyl, dichlorvos-sulfuron-methyl, fluroxypyr, bispyribac-sodium, pyrimisulfuron-methyl, pyrimisulfuron-methyl, pyrimisulfuron-methyl, bispyribac-sodium, nicosulfuron-methyl, sulfadiazine, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, isoxazolidinone, isoxazolidinone, Fenoxasulfone, Me thiozolin, isopropalazine, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, bensulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flumetsulam, pyrazosulfuron, pyrazosulfuron, flumethrin, mesotrione, pyrazosulfuron, flupropalazine, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, flupropalazine, pyrazosulfuron, flupropalazine, pyrazosulfuron, flupropalazine, pyrazosulfuron, flumezin, pentachlorophenol (sodium), terliphenol, terliphenol, terliphenol, pentonitrophenol, dinitrophenol, chlorpyrifos, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron, terlisulfuron Flupyrazosulfuron, methyl methacrylate, tetrazolium methoxysulfuron, flupyrazosulfuron, chlorpyrifos, bromochlor, dimethoate, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, pyrazosulfuron, bentazon, pyrazosulfuron, oxadiazon, pyrazosulfuron, isoxadiazon, cyclohexane, isopropyl methoxysulfuron, propyl methoxysulfuron, indicarb, sodium chlorate, cogongrass Trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, forage fastener, bromophenol oxime, triazole sulfonate, methomyl, furazolidone, furazolidone, ethoxysulfuron, pyrimethanil, chlorphthalic acid, flurfluthrin, barnyardgrass, acrolein, bensulfuron-methyl, metribuzin, oat ester, thiamethoxam, styracil, hydroxyzine, methoxybenzone, pyrimethanil, chlorpyrifos, trichloropropionic acid, Alora c. Diethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, methylsulfuron, Cambendichlor, Cyproterinic acid, Thiamethoxam, Etnipromidone, Etnipromidone, Etnipromidone-methyl ...LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO 535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

[0080] 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

[0081] 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 application claimed is set forth in the claims. In view of the economics and diversity of compounds, we have synthesized a number of compounds, of which a selection is listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Tables 1-2. The compounds in Table 1 are only for better illustrating the present application, but do not limit the present application, and for those skilled in the art, should not be construed as the scope of the above-mentioned subject matter of the present application is limited to the following compounds.

[0082] Table 1 Compound Structures

[0083] Table 2 Compounds 1 H NMR

[0084] Several methods for preparing the compounds of the present application are illustrated in the following Schemes and Examples. Starting materials can be purchased from vendors or can be prepared by known methods in the literature 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 below, other suitable starting materials and conditions can be readily adapted and are included in the present application. In addition, the synthetic methods described below can be further modified to produce additional compounds of the present application using conventional chemistry as known to those skilled in the art.

[0085] The following method examples are provided to further illustrate the preparation of the compounds of the present application and are not intended to limit the scope of the application. The reagents used in the synthesis of the compounds described below can be purchased from vendors or can be readily prepared by one of ordinary skill in the art.

[0086] Representative compounds are prepared as follows, and other compounds are prepared in a similar manner.

[0087] 1. Synthesis of Compound 2

[0088] Compound 2-2 (2.3 g, 9.6 mmol) was dissolved in toluene 50 mL and cooled to -78 °C with dry ice-ethyl acetate bath. n-BuLi solution (3.3 mL, 8.2 mmol) was added slowly. The temperature was kept low for 2 h, then compound 2-1 (2.0 g, 6.3 mmol) was dissolved in toluene 1.5 mL and added slowly to the system. The reaction was monitored by LCMS and was completed in 1 h. The reaction was concentrated and extracted with ethyl acetate three times. The organic phase was combined and dried over anhydrous sodium sulfate. The sample was concentrated and purified by normal phase to give compound 2 (600 mg, yield 22%).

[0089] 2. Synthesis of Compound 1

[0090] Compound 2 (150 mg, 0.35 mmol) was dissolved in DCM and the reaction flask was placed in an ice bath. Phosphorous tribromide (190 mg, 0.70 mmol) was added slowly dropwise with stirring. The reaction was allowed to warm to room temperature and was left overnight. The reaction was monitored by LCMS and was completed. The reaction was quenched by pouring slowly into ice water and extracted with dichloromethane three times. The organic phase was combined and dried over anhydrous sodium sulfate. The sample was concentrated and purified by normal phase to give compound 1 (80 mg, yield 55%).

[0091] 3. Synthesis of compound 79

[0092] (1) Compound 79-1 (15.0 g, 1.0 eq) was dissolved in 150 mL mixed solvent (dioxane: H2O = 10:1), DPPF palladium dichloride methane complex (1.76 g, 0.03 eq), potassium carbonate (29.75 g, 3 eq) and compound 79-2 (10.0 g, 0.8 eq) were added, 40 °C stirring for 1 h, LCMS monitoring reaction complete, product main peak. EA and water were added to extract, the organic phase was dried and concentrated. The residue was purified by column chromatography to obtain compound 79-3 (4.08 g, yield 18.8%).

[0093] (2) Compound 2-2 (4.85 g, 1.5 eq) was dissolved in 100 mL of toluene, protected by nitrogen, and n-butyllithium (8.0 mL, 1.5 eq) was added dropwise at -78 °C. After stirring for 2 h, compound 79-3 (4.08 g, 1.0 eq) was added and stirred at room temperature for 1 h. LCMS monitoring showed that the reaction was complete and the product was the main peak. Ice water was added to quench the reaction, and EA was added to extract the organic phase, which was dried and concentrated. The residue was purified by column chromatography to obtain compound 79 (3.12 g, yield 55.6%).

[0094] 4. Synthesis of compound 78

[0095] Compound 79 (500 mg, 1.0 eq) was dissolved in 50 mL of DCM, and PBr3 (2.9 g, 3.0 eq) was added dropwise at 0 °C. After stirring at room temperature for 12 h, LCMS monitoring showed that the reaction was complete and the product was the main peak. Ice water was added to quench the reaction, and the organic phase was dried and concentrated. The residue was purified by column chromatography to obtain compound 78 (91 mg, yield 18.9%).

[0096] Biological activity evaluation:

[0097] The activity level criteria for plant destruction (i.e., growth control rate) are as follows:

[0098] 9: complete death;

[0099] 8: growth control rate greater than or equal to 90% and less than 100%;

[0100] 7: growth control rate greater than or equal to 80% and less than 90%;

[0101] 6: growth control rate greater than or equal to 70% and less than 80%;

[0102] 5: growth control rate greater than or equal to 50% and less than 70%;

[0103] Grade 4: growth control rate is greater than or equal to 30% and less than 50%;

[0104] Grade 3: growth control rate is greater than or equal to 20% and less than 30%;

[0105] Grade 2: growth control rate is greater than or equal to 10% and less than 20%;

[0106] Grade 1: growth control rate is less than 10%;

[0107] Grade 0: no effect.

[0108] The above growth control rate is fresh weight control rate.

[0109] Post-emergence test experiment:

[0110] The seeds of monocotyledonous and dicotyledonous weeds and the seeds of main crops are placed in plastic pots filled with soil, and then covered with 0.5-2 cm of soil, and the test plants are treated 2 weeks after sowing in a good greenhouse environment. The tested compounds of the present application are dissolved in acetone, and then Tween 80 is added, and 0.9 L / ha of methyl oleate emulsion is used as a synergist, and a certain concentration of solution is diluted with water, and sprayed on the plants by a spray tower. After the application, the test plants are cultured in the greenhouse for 2-3 weeks, and the experimental results of weeds are counted, and the representative data are listed in Table 3.

[0111] Table 3 Post-emergence test experiment results

[0112] Note: N represents no data.

[0113] Pre-emergence test experiment:

[0114] The seeds of monocotyledonous and dicotyledonous weeds and the seeds of main crops are placed in plastic pots filled with soil, and then covered with 0.5-2 cm of soil, and the test plants are treated 2 weeks after sowing in a good greenhouse environment. The tested 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 the application, the test plants are cultured in the greenhouse for 4 weeks, and the experimental results are observed, and the representative data are listed in Table 4.

[0115] Table 4 Pre-emergence test experiment results

[0116] At the same time, through many tests, it is found that the compounds and compositions of the present application can prevent many key grass weeds, broadleaf weeds and sedge weeds, etc., and show excellent commercial value.

[0117] Finally, it should be noted that the above examples are merely used to illustrate the technical solutions of the present application but not to limit the present application. 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 equivalent replaced without departing from the spirit and scope of the technical solutions of the present application.

Claims

1. A substituted heterocyclic compound of the formula I: ###0001### or a salt thereof. wherein, Q1, Q2, Q3 independently represent N or CR5; X represents aryl or heteroaryl; Y represents hydrogen, -OY1, -(CO)OY2, -(CO)SY2 or -(CO)N(Y2)2; Y1represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, -(CO)R 21 or -(CO)OR 21 , said alkyl, alkenyl or alkynyl being optionally substituted by at least one radical chosen from halogen, cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2; Y2represents independently for each occurrence hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl, said alkyl, alkenyl or alkynyl being optionally substituted with at least one member selected from the group consisting of halogen, cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2; R1, R2, R3, R4, R5, independently, represent hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -(CO)N(R 21 )2, -S(O) n R 21 or -N(R 21 )2, said alkyl, alkenyl or alkynyl being optionally substituted with at least one group selected from halogen, cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2; n is 0, 1 or 2; R 21 each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl, said alkyl, alkenyl, or alkynyl being optionally substituted with at least one group selected from halo or alkoxy; the foregoing cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -O(CO)R 10 , -(CO)N(R 10 )2, -(CS)N(R 10 )2, -(SO)R 10 or -(SO2)R 10 ; R 10 are independently of each other hydrogen, alkyl, haloalkyl, aryl or heterocyclyl, which are unsubstituted or substituted by at least one group selected from the group consisting of halogen, alkyl; Excluded are the following compounds:

2. The substituted heterocyclic compound according to claim 1, wherein Y1represents hydrogen, Ci-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, aryl, heterocyclyl, -(CO)R 21 or -(CO)OR 21 , said Ci-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one radical chosen from halogen, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2; Y2represents independently for each occurrence hydrogen, Ci-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, aryl or heterocyclyl, said Ci-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted with at least one group selected from halogen, C3-C8cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2; R1, R2, R3, R4, R5, independently of one another, represent hydrogen, halogen, cyano, nitro, Ci-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C8-cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -(CO)N(R 21 )2, -S(O) n R 21 or -N(R 21 )2, it being possible for said Ci-C8-alkyl, C2-C8-alkenyl or C2-C8-alkynyl to be optionally substituted by at least one radical from the group consisting of halogen, C3-C8-cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2; n is 0, 1 or 2; R 21 each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, arylC1-C8alkyl, heterocyclyl or heterocyclylC1-C8alkyl, said C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl being optionally substituted by at least one group selected from halogen or C1-C8alkoxy; C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -O(CO)R 10 , -(CO)N(R 10 )2, -(CS)N(R 10 )2, -(SO)R 10 , or -(SO2)R 10 ; R 10 are independently from each other and within each group independently from each other hydrogen, C1-C8-alkyl, halo-C1-C8-alkyl, aryl or heterocyclyl, which is unsubstituted or substituted by at least one group selected from the group consisting of halogen, C1-C8-alkyl.

3. The substituted heterocyclic compound according to claim 1, wherein Y1represents hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, aryl, heterocyclyl, -(CO)R 21 or -(CO)OR 21 , said Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl being optionally substituted with at least one radical selected from halogen, C3-C6-cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2; Y2represents independently for each occurrence hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, aryl or heterocyclyl, said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl being optionally substituted with at least one group selected from halogen, C3-C6cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2; R1, R2, R3, R4, R5, independently of one another, represent hydrogen, halogen, cyano, nitro, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)R 21 , -(CO)OR 21 , -(CO)N(R 21 )2, -S(O) n R 21 or -N(R 21 )2, it being possible for said Ci-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl to be optionally substituted by at least one radical from the group consisting of halogen, C3-C6-cycloalkyl, aryl, heterocyclyl, -OR 21 , -(CO)OR 21 , -S(O) n R 21 or -N(R 21 )2; n is 0, 1 or 2; R 21 each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, aryl, arylC1-C6alkyl, heterocyclyl or heterocyclylC1-C6alkyl, said C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl being optionally substituted by at least one group selected from halogen or C1-C6alkoxy; C3-C6cycloalkyl, heterocyclyl, aryl or heteroaryl is optionally substituted with at least one radical selected from the group consisting of oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, halogenated C1-C6alkyl, halogenated C2-C6alkenyl, halogenated C2-C6alkynyl, -OR 10 , -SR 10 , -(CO)R 10 , -(CO)OR 10 , -O(CO)R 10 , -(CO)N(R 10 )2, -(CS)N(R 10 )2, -(SO)R 10 or -(SO2)R 10 ; R 10 are independently from each other and within one definition independently from definition (A) hydrogen, C1-C6-alkyl, halo-C1-C6-alkyl, aryl or heterocyclyl, which are unsubstituted or substituted by at least one group selected from the group consisting of halogen, C1-C6-alkyl; Preferably, the compound is selected from any one of Table 1 in the specification.

4. A method for preparing the substituted heterocyclic compound according to any one of claims 1-3, comprising the following steps: When Y represents -(CO)OY2, -(CO)SY2, or -(CO)N(Y2)2, a compound of the formula II is reacted with a compound of the formula III to give a compound of the formula I', as shown in the following reaction equation: When Y represents OY1, the compound of general formula IV or a compound of Formula V to yield a compound of Formula I" by reaction with a compound of Formula III then the target compound is prepared through a substitution reaction; when Y is hydrogen, the compound is prepared from a compound as shown in general formula I’ through a hydrolytic decarboxylation reaction, or from a compound as shown in general formula I” through a reduction reaction; wherein Hal represents halogen, and the definitions of substituents X, Y, R1, R2, R3, R4, Q1, Q2 and Q3 are as described in any one of claims 1-3; Preferably, the reaction for preparing the compound of general formula I’ or I” is carried out in the presence of a base and a solvent; more preferably, the base is selected from at least one of inorganic bases or organic bases, and the solvent is selected from at least one of toluene, dichloroethane, dimethyl sulfoxide, acetonitrile, ethyl acetate, diethyl ether, hexane or tetrahydrofuran.

5. A herbicidal composition, characterized by comprising: comprising at least one of the substituted heterocyclic compounds according to any one of claims 1-3 in a herbicidally effective amount; preferably, further comprising a formulation auxiliary; more preferably, further comprising other effective ingredients.

6. A method for controlling weeds, comprising applying a herbicidally effective amount of at least one of the substituted heterocyclic compounds according to any one of claims 1-3 or the herbicide composition according to claim 5 on plants or in the area of weeds.

7. Use of the substituted heterocyclic compound according to any one of claims 1-3 or the composition according to claim 5 in controlling weeds, preferably, the substituted heterocyclic compound is used for preventing weeds in useful crops, and the useful crops are genetically modified crops or crops treated by genome editing technology.

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