Herbicide compound as well as preparation method and application thereof

Abstract

The invention discloses a compound as shown in the following formula I, a stereoisomer, a racemate, a tautomer, nitrogen oxide or pharmaceutically acceptable salt of the compound, and the compound serving as a herbicide is high in herbicidal activity, low in toxicity, small in dosage and small in environmental pollution and has a good application prospect.

Description

Technical Field

[0001] This invention relates to the field of pesticides, specifically to a herbicide compound, its preparation method, and its application. Background Technology

[0002] Pesticides are substances and their formulations used to prevent, control, and eliminate pests, weeds, and other harmful organisms that damage agriculture and forestry. They are used to purposefully regulate plant and insect growth and can be derived from chemical synthesis, biological sources, or other natural substances. Pesticides play a crucial role in agricultural production, primarily used to remove weeds, prevent pest and disease infestations, protect crops, and ensure increased agricultural and livestock yields. They also help prevent the spread of diseases. As of 2010, the global population had reached 7 billion and continues to grow, while the area under grain cultivation has been declining, falling to 6.8 billion hectares. 2 Furthermore, the planting structure is also changing, and clearly, the food supply will become increasingly strained. According to estimates by the Food and Agriculture Organization of the United Nations (FAO), 35% of the world's food and 33.8% of its cotton are lost annually due to diseases, pests, and weeds. Experiments have shown that without pesticides, crop yields would decrease by approximately 74.75% due to diseases, pests, and weeds. Therefore, pesticides are one of the necessary means to ensure food supply. Non-agricultural pesticides account for approximately 14% of the global pesticide market, and this figure is increasing annually. Their application is very broad, including material protection, rodent control, cultural relics, and gardens, all of which have a significant impact on human life. While recognizing the positive role of pesticides, we must also clearly understand that pesticides do have adverse effects on both the environment and human health. Some traditional pesticides are indeed highly toxic and have high residues, such as methamidophos. Some pesticides have also been found to have carcinogenic, teratogenic, and mutagenic effects, such as amitraz. In addition, the irrational use of pesticides can also trigger a series of environmental problems. However, newly developed pesticides in recent years have generally had low toxicity and have undergone extensive testing to confirm their absence of carcinogenic, teratogenic, and mutagenic effects before being released to the market. Undoubtedly, given the indispensable role pesticides play in human production and daily life, the rational use of pesticides and the development of environmentally friendly and sustainable green pesticides have become an inevitable trend. Currently, the global direction of pesticide development emphasizes both high activity and safety to ensure the safety of non-target organisms, humans, and the environment.

[0003] Herbicides primarily target weeds, which are plants that, besides the target plant, have adapted to the local soil, cultivation methods, and climate. These weeds compete with the target plant for water, light, and nutrients, affecting its photosynthesis, growth, yield, and quality. In the 1960s, among the three major categories of pesticides—insecticides, fungicides, and herbicides—herbicides accounted for only about 20% of the global pesticide market, ranking last. However, since the 1970s, the herbicide market has consistently dominated, and since the 1990s, it has maintained a 46%-50% share of the global pesticide market, consistently ranking first among pesticides with sales exceeding $100 million worldwide. Currently, "high efficiency, low toxicity, and safety" have become the themes of new pesticide research and development, and herbicide development is no exception. Among the three major categories of pesticides, herbicides have been the most thoroughly researched, and the most new varieties have been developed. According to the United Nations Agricultural Organization, there are more than 50,000 types of weeds worldwide, and more than 8,000 of them harm the growth of crops in farmland. Therefore, the development of herbicides is extremely urgent and a long way to go.

[0004] Uracil compounds are milestone compounds among protoporphyrinogen oxidase (PPO) inhibitors. They are easily absorbed by roots, shoots, and leaves, and once absorbed, they are mainly translocated upwards through the xylem to various parts of the weed. PPO is an essential enzyme for chlorophyll biosynthesis in plants. PPO inhibitor herbicides compete with protoporphyrinogen IX for binding sites at or near the catalytic site of PPO, inhibiting the enzyme-catalyzed oxidation reaction and leading to the excessive accumulation of protoporphyrinogen IX. Protoporphyrinogen IX is a photosensitizer; under aerobic and light conditions, it can generate highly reactive singlet oxygen, which acts on the cell membrane, causing a peroxidation reaction. The byproducts ultimately lead to cell necrosis, and finally, plant death.

[0005] The prior art WO01 / 83459 describes a uracil compound, phenylsulfuron-methyl (CAS: 372137-35-4), which has herbicidal activity. Its structure is as follows:

[0006]

[0007] This compound exhibits poor selectivity as a herbicide, requires large dosages, and is environmentally unfriendly. Therefore, there is a need to develop novel herbicides that are highly active, require low dosages, and cause minimal environmental pollution. Summary of the Invention

[0008] The purpose of this invention is to provide a new uracil compound that is highly active, requires low dosage, and causes minimal environmental pollution.

[0009] This invention provides compounds of Formula I, their stereoisomers, racemates, tautomers, nitrides, or pharmaceutically acceptable salts.

[0010]

[0011] Among them, R1, R2, R3, R4, R5, and R6 may be the same or different, and are independently selected from hydrogen, halogen, cyano, unsubstituted, or optionally surrounded by one, two, or more R groups. a The following groups are substituted: C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 cycloalkyl, C1-C 10 Alkoxy, halogenated C3-C 10 Cycloalkyl-O-, C2-C 10 alkenyl, C2-C 10 alkynyl group, C1-C 10 Alkyl-C(O)-, C1-C 10 Alkyl-OC(O)-, C6-C 10 Aryl, C6-C 10 Aryl-O-, C6-C 10 Aryl-C(O)-, C6-C 10 Aryl-OC(O)-; each R a They are the same or different, and are independently selected from halogens, C1-C. 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 cycloalkyl, halogenated C3-C 10 cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, halogenated C3-C 10 At least one of cycloalkyl-O-;

[0012] R7 is selected from halogens, unsubstituted, or optionally surrounded by one, two, or more R7 groups. b The following groups are substituted: C1-C 10 Alkoxy, C3-C 10 Cycloalkyl-O-, C6-C 10 Aryl, 3-10 heteroaryl; each R b They are the same or different, and are independently selected from halogens, C1-C. 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 cycloalkyl, halogenated C3-C 10 cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, halogenated C3-C10 At least one of cycloalkyl-O-;

[0013] X is selected from C(O)O, unsubstituted or R-substituted. c Substituted C(O)NH;R c Selected from C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 cycloalkyl, halogenated C3-C 10 At least one of the cycloalkyl groups.

[0014] According to embodiments of the present invention, R1, R2, R3, R4, R5 and R6 may be the same or different, and are independently selected from hydrogen, halogen, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, halo-C1-C6 alkyl, halo-C3-C8 cycloalkyl, and halo-C1-C6 alkoxy.

[0015] According to an embodiment of the present invention, R1 is selected from halogenated C1-C3 alkyl groups, such as trifluoromethyl.

[0016] According to an embodiment of the present invention, R2 is selected from C1-C3 alkyl groups, such as methyl.

[0017] According to an embodiment of the present invention, R3 is selected from halogens, such as F.

[0018] According to an embodiment of the present invention, R4 is H.

[0019] According to an embodiment of the present invention, R5 is selected from halogens, such as Cl.

[0020] According to an embodiment of the present invention, R6 is H.

[0021] According to an embodiment of the invention, R7 is selected from unsubstituted or optionally replaced by one, two or more Rs. b Substituted 5-6 membered heteroaryl groups (e.g., thiadiazolyl); each R b They may be the same or different, and are independently selected from C1-C6 alkyl groups (e.g., methyl);

[0022] According to an embodiment of the present invention, R7 is selected from...

[0023] According to an embodiment of the present invention, R7 is selected from methylthiadiazole, for example...

[0024] According to an embodiment of the present invention, the compound represented by Formula I is:

[0025]

[0026] The present invention also provides a method for preparing a compound of formula I, comprising the following steps: reacting compound a with compound b to obtain the compound shown in formula I;

[0027]

[0028] Among them, R1, R2, R3, R4, R5, R6, R7 and X have the definitions described above independently of each other.

[0029] According to an embodiment of the present invention, the preparation method can be carried out in the presence of a solvent selected from water and / or organic solvents. The organic solvent can be selected from polar solvents or non-polar solvents, such as at least one of: diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, DMF, DMA, NMP, dioxane, dichloromethane, dichloroethane, chloroform, carbon tetrachloride, benzene, xylene, nitrobenzene, chlorobenzene, and dichlorobenzene.

[0030] According to an embodiment of the present invention, the preparation method can be carried out in the presence of an alkali, which can be selected from inorganic or organic alkalis. The inorganic alkali can be selected from at least one of sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, potassium hydroxide, sodium hydroxide, sodium hydride, and potassium hydride. The organic alkali can be selected from at least one of methylamine, dimethylamine, trimethylamine, triethylamine, diisopropylamine, diethylmethylamine, diisopropylethylamine, sodium formate, potassium formate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, and DBU.

[0031] According to an embodiment of the present invention, a condensing agent may be added to the preparation method. The condensing agent is selected from commonly used condensing agents in the art, such as at least one selected from EDC, EDCI, CDI, DCC, and HATU (2-(7-benzotriazole oxide)-N,N,N',N'-tetramethylurea hexafluorophosphate).

[0032] The present invention also provides a pesticide composition comprising at least one of the following as active ingredients: a compound of formula I, a stereoisomer thereof, a racemic mixture thereof, a tautomer thereof, a nitrogen oxide thereof, or a pharmaceutically acceptable salt thereof.

[0033] According to an embodiment of the present invention, the pesticide composition is a herbicide.

[0034] According to an embodiment of the present invention, the grass is barnyard grass.

[0035] According to an embodiment of the present invention, the active ingredient in the pesticide composition has a weight percentage of 0.1-99.9%, for example, 0.5-99%.

[0036] According to embodiments of the present invention, the pesticide composition further includes one, two, or more of agriculturally and / or forestry and / or sanitarily acceptable carriers.

[0037] According to an embodiment of the present invention, the pesticide composition can be applied in the form of a formulation.

[0038] For example, the compound shown in Formula I is dissolved or dispersed in a carrier or formulated as an active ingredient to facilitate dispersion when used as a herbicide.

[0039] According to embodiments of the present invention, the formulation includes, but is not limited to, the following forms: wettable powder, oil suspension, water suspension, water emulsion, aqueous solution, emulsifiable concentrate or microcapsule, etc.

[0040] According to an embodiment of the invention, a liquid or solid carrier and optionally a surfactant may also be added to the pesticide composition.

[0041] The present invention also provides the use of one, two or more of the compounds of Formula I, their stereoisomers, racemates, tautomers, nitrogen oxides or pharmaceutically acceptable salts thereof, as pesticides, such as herbicides.

[0042] The present invention also provides the use of one, two or more of the compounds of Formula I, their stereoisomers, racemates, tautomers, nitrogen oxides or pharmaceutically acceptable salts thereof in the preparation of pesticides, such as herbicides.

[0043] The present invention also provides a method for weed control, comprising applying an effective amount of one, two or more of the following: a compound of formula I, its stereoisomers, racemates, tautomers, nitrogen oxides or pharmaceutically acceptable salts thereof, or the pesticide composition thereof, to a medium in which crops grow.

[0044] According to an embodiment of the present invention, the crop is rapeseed.

[0045] According to an embodiment of the present invention, the grass is barnyard grass.

[0046] According to an embodiment of the present invention, the effective amount is 10 to 1000 grams per hectare, preferably 20 to 500 grams per hectare.

[0047] When the compounds of the present invention can exist in tautomer form, the compounds described above and below should be understood, where applicable, to also include the corresponding tautomer forms, even if such tautomer forms are not explicitly mentioned in each case.

[0048] If the compound of Formula I described in this invention has one or more chiral centers and is therefore present as an enantiomer or diastereomer, then the pure enantiomer, the racemic version, or the diastereomer may be used in the compositions of this invention.

[0049] Any asymmetric atom (e.g., carbon, etc.) in the compounds disclosed in this invention can exist in racemic or enantiomerically enriched forms, such as (R)-, (S)-, or (R,S)- configurations.

[0050] If the compounds of Formula I described in this invention have functional groups that can be ionized, they can also be used as agricultural salts or mixtures thereof. The salts described in this invention can be inorganic salts such as hydrochlorides, hydrobroms, sulfates, nitrates, and phosphates, but are not limited thereto. They can also be organic acid salts such as formates, acetates, oxalates, fumarates, methanesulfonates, and benzenesulfonates, but are not limited thereto.

[0051] Beneficial effects

[0052] This invention provides a uracil compound of formula I, which is highly active, requires low dosage, and causes minimal environmental pollution. As a herbicide, it can achieve good control effects at very low dosages, exhibits high selectivity and a broad spectrum of weed control, and is effective against barnyard grass and other noxious weeds.

[0053] Terminology Definitions and Explanations

[0054] Unless otherwise stated, the definitions of groups and terms recorded in this application specification and claims, including definitions as examples, exemplary definitions, preferred definitions, definitions recorded in tables, and definitions of specific compounds in the examples, can be arbitrarily combined and combined with each other. Such combinations and combinations of group definitions and compound structures should be understood as being within the scope of this application specification and / or claims.

[0055] Unless otherwise expressly stated, throughout the specification and claims, the term "comprising" or its variations such as "including" or "comprises" shall be understood to include the stated ingredients or steps without excluding the presence of other material ingredients or steps.

[0056] Term "C" 1- C 10 "alkyl" should be understood to preferably represent a straight-chain or branched saturated monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably C14. 1- C8 alkyl. "C" 1-"C8 alkyl" should be understood to preferably represent a straight-chain or branched saturated monovalent hydrocarbon group having 1, 2, 3, 4, 5, 6, 7, or 8 carbon atoms. The alkyl group is, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neopentyl, 1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl, or 1,2-dimethylbutyl, or their isomers. In particular, the group has 1, 2, 3, 4, 5, 6, or 8 carbon atoms ("C8 alkyl") 1-6 Alkyl groups, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, and more particularly, the groups having 1, 2, or 3 carbon atoms (“C”). 1-3 Alkyl), such as methyl, ethyl, n-propyl or isopropyl.

[0057] The term "C2-C" 10"Alkenyl" should be understood to mean a straight-chain or branched monovalent hydrocarbon group containing one or more double bonds and having 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms, more preferably "C2-C8 alkenyl". "C2-C8 alkenyl" should be understood to preferably mean a straight-chain or branched monovalent hydrocarbon group containing one or more double bonds and having 2, 3, 4, 5, 6, 7, or 8 carbon atoms, for example, having 2, 3, 4, 5, or 6 carbon atoms (i.e., C2-C6 alkenyl), or having 2 or 3 carbon atoms (i.e., C2-C3 alkenyl). It should be understood that the alkenyl group contains multiple... In the case of a single double bond, the double bonds can be separable or conjugated. The alkenyl group is, for example, vinyl, allyl, (E)-2-methylvinyl, (Z)-2-methylvinyl, (E)-but-2-enyl, (Z)-but-2-enyl, (E)-but-1-enyl, (Z)-but-1-enyl, pent-4-enyl, (E)-pent-3-enyl, (Z)-pent-3-enyl, (E)-pent-2-enyl, (Z)-pent-2-enyl, (E)-pent-1-enyl, (Z)-pent-1-enyl, hex-5-enyl, (E)-hex- 4-Alkenyl, (Z)-hex-4-alkenyl, (E)-hex-3-alkenyl, (Z)-hex-3-alkenyl, (E)-hex-2-alkenyl, (Z)-hex-2-alkenyl, (E)-hex-1-alkenyl, (Z)-hex-1-alkenyl, isopropenyl, 2-methylprop-2-alkenyl, 1-methylprop-2-alkenyl, 2-methylprop-1-alkenyl, (E)-1-methylprop-1-alkenyl, (Z)-1-methylprop-1-alkenyl, 3-methylbut-3-alkenyl, 2-methylbut-3-alkenyl, 1-methylbut-3-alkenyl, 3-methylbut-2-alkenyl (E)-2-methylbut-2-enyl, (Z)-2-methylbut-2-enyl, (E)-1-methylbut-2-enyl, (Z)-1-methylbut-2-enyl, (E)-3-methylbut-1-enyl, (Z)-3-methylbut-1-enyl, (E)-2-methylbut-1-enyl, (Z)-2-methylbut-1-enyl, (E)-1-methylbut-1-enyl, (Z)-1-methylbut-1-enyl, 1,1-dimethylprop-2-enyl, 1-ethylprop-1-enyl, 1-propylvinyl, 1-isopropylvinyl.

[0058] The term "C2-C" 10"Alynyl" should be understood as representing a straight or branched monovalent hydrocarbon group containing one or more triple bonds and having 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. For example, having 2, 3, 4, 5, 6, 7, or 8 carbon atoms (i.e., "C2-C8 alkynyl"), having 2, 3, 4, 5, or 6 carbon atoms (i.e., "C2-C6 alkynyl"), having 2 or 3 carbon atoms ("C2-C3 alkynyl"), etc. The alkynyl group is, for example, ethynyl, prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 1-methylprop-2-ynyl, 2-methylbut-3-ynyl, 1-methyl Butyl-3-ynyl, 1-methylbutyl-2-ynyl, 3-methylbutyl-1-ynyl, 1-ethylpropyl-2-ynyl, 3-methylpentyl-4-ynyl, 2-methylpentyl-4-ynyl, 1-methylpentyl-4-ynyl, 2-methylpentyl-3-ynyl, 1-methylpentyl-3-ynyl, 4-methylpentyl-2-ynyl, 1-methylpentyl-2-ynyl, 4-methylpentyl-1-ynyl, 3-methylpentyl-1-ynyl 2-Ethylbut-3-ynyl, 1-Ethylbut-3-ynyl, 1-Ethylbut-2-ynyl, 1-Prop-2-ynyl, 1-Isopropylp-2-ynyl, 2,2-Dimethylbut-3-ynyl, 1,1-Dimethylbut-3-ynyl, 1,1-Dimethylbut-2-ynyl, or 3,3-Dimethylbut-1-ynyl. In particular, the ynyl group is ethynyl, prop-1-ynyl, or prop-2-ynyl.

[0059] Term "C" 1- C 10 "Alkoxy" should be understood as "C". 1- C 10 alkyl-O-”, where “C” 1- C 10 "alkyl" has the definition as described above, and is preferably "C 1- "C8 alkoxy". Specifically, the group has 1, 2, 3, 4, 5, or 6 carbon atoms ("C8 alkoxy"). 1-6 Alkoxy groups, such as methoxy, ethoxy, propoxy, butoxy, tert-butoxy, and more particularly, said groups having 1, 2, or 3 carbon atoms (“C”). 1-3 Alkoxy groups, such as methoxy, ethoxy, n-propoxy, or isopropoxy.

[0060] In this invention, the halogen is typically fluorine, chlorine, bromine, or iodine, preferably fluorine, bromine, or chlorine. Accordingly, this also applies to halogens bonded to other structures, such as halogenated C. 1- C 10 Alkyl group. Halogenated C 1- C 10Alkyl groups preferably have 1 to 6 carbon atoms (e.g., halogenated C). 1- C6 alkyl), more preferably having 1 to 4 carbon atoms (such as halogenated C6 alkyl), 1- (C4 alkyl). The alkyl halogroup is selected from fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, difluorochloromethyl and dichlorofluoromethyl.

[0061] The term "C3-C" 10 "Cycloalkyl" should be understood to refer to a saturated monovalent monocyclic alkane having 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms, preferably "C". 3-8 "Cycloalkyl", more preferably "C" 3-6 cycloalkyl. The term "C" 3-10 "Cycloalkyl" should be understood to refer to a saturated monovalent monocyclic, bicyclic (e.g., bridged, spirocyclic) hydrocarbon ring or tricyclic alkane having 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. The C... 3-10 Cycloalkyl groups can be monocyclic hydrocarbon groups, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, or cyclodecyl; or bicyclic hydrocarbon groups, such as borneolyl, indolyl, hexahydroindolyl, tetrahydronaphthyl, decahydronaphthyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]heptenyl, 6,6-dimethylbicyclo[3.1.1]heptyl, 2,6,6-trimethylbicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl, 2,7-diazaspiro[3,5]nonyl, 2,6-diazaspiro[3,4]octyl; or tricyclic hydrocarbon groups, such as adamantyl.

[0062] The term "C6-C" 10 "Aryl" should be understood to preferably represent a monovalent aromatic or partially aromatic monocyclic, bicyclic, or tricyclic hydrocarbon ring having 6, 7, 8, 9, or 10 carbon atoms, particularly a ring having 6 carbon atoms ("C6 aryl"), such as phenyl; or biphenyl, or a ring having 9 carbon atoms ("C9 aryl"), such as indenyl or indenyl, or a ring having 10 carbon atoms ("C9 aryl"). 10 Aryl), such as tetrahydronaphthyl, dihydronaphthyl or naphthyl.

[0063] The term "5-10 cyclic heteroaryl" should be understood to include monovalent monocyclic, bicyclic, or tricyclic aromatic ring systems having 5, 6, 7, 8, 9, or 10 ring atoms, particularly 5, 6, 9, or 10 carbon atoms, and containing 1-5, preferably 1-3, heteroatoms independently selected from N, O, and S. Furthermore, in each case, it may also be benzofused. Specifically, the heteroaryl group is selected from thienyl, furanyl, pyrroleyl, oxazolyl, thiazolyl, imidazoleyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, thia-4H-pyrazolyl, and their benzo[derivatives], such as benzofuranyl, benzothienyl, benzooxazolyl, benzoisooxazolyl, benzoimidazolyl, benzotriazolyl, indazole, indolyl, isindolyl, etc.; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and their benzo[derivatives], such as quinolinyl, quinazolinyl, isoquinolinyl, etc.; or acrylinyl, inazinyl, purinyl, and their benzo[derivatives]; or terpenolyl, phthalazinyl, quinazolinyl, quinoxolinyl, naphridinyl, pteridinyl, carbazolyl, acridineyl, phenazinyl, phenothiazinyl, phenothiazinyl, etc. Detailed Implementation

[0064] The technical solutions of this disclosure will be further described in detail below with reference to specific embodiments. It should be understood that the following embodiments are merely illustrative and explanatory of this disclosure and should not be construed as limiting the scope of protection of this disclosure. All technologies implemented based on the above content of this disclosure are covered within the scope of protection intended by this disclosure.

[0065] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods.

[0066] Example 1

[0067] Synthesis of 2-chloro-4-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzamide

[0068]

[0069] In a 250ml four-necked flask equipped with a stirrer, thermometer, and condenser, 50ml of THF, 3.6g of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoic acid, 1g of 5-methyl-1,3,4-oxadiazol-2-amine, 10g of HATU, and 3g of triethylamine were added. The mixture was stirred at room temperature for three hours until the reaction of the starting materials was completed. After rotary evaporation, washing, and column chromatography purification, 3g of 2-chloro-4-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzamide was obtained. 1 H NMR (400MHz, DMSO) δ7.96–7.75(m,2H,H-4,5),6.60(s,1H,H-3),5.05(m,0.7H),4.90(m,0.3H),3.69(s,3H,H-1),3.42(s,3H,H-2).

[0070] Test Example 1

[0071] Biological testing:

[0072] 1. Testing the herbicidal activity of the compounds of this invention.

[0073] 2. Preparation of the reagent: Dissolve the compound of the present invention in DMF and bring it to a certain concentration using 0.2% Tween-80 solution.

[0074] 3. Test methods:

[0075] 3.1 Post-emergence treatment experiment

[0076] Seeds of barnyard grass and rapeseed were sown in paper cups filled with nutrient soil (7 cm in diameter). After sowing, the seeds were covered with 1 cm of soil, compacted, and watered. The plants were then cultivated in a greenhouse using conventional methods. Once the weeds reached the 2-3 leaf stage, post-emergence foliar spraying was applied. The treated plants and control groups were observed in the greenhouse for 7 days.

[0077] 4. Survey Methods

[0078] Weed mortality rates are statistically analyzed to determine the efficacy of herbicides.

[0079]

[0080] 5. Results

[0081] Table 1. Results of post-seeding treatment activity of the compounds of the present invention.

[0082]

[0083] The above description provides an exemplary account of the implementation methods of the technical solution disclosed herein. It should be understood that the scope of protection of this disclosure is not limited to the above-described embodiments. Any modifications, equivalent substitutions, or improvements made by those skilled in the art within the spirit and principles of this disclosure should be included within the scope of protection of the claims of this application.

Claims

1. The compound represented by Formula I, its stereoisomers, racemates, tautomers, nitrides, or pharmaceutically acceptable salts, in, R1, R2, R3, R4, R5, and R6 may be the same or different, and are independently selected from hydrogen, halogen, cyano, unsubstituted, or optionally substituted by one, two, or more R groups. a The following groups are substituted: C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 cycloalkyl, C1-C 10 Alkoxy, halogenated C3-C 10 Cycloalkyl-O-, C2-C 10 alkenyl, C2-C 10 alkynyl group, C1-C 10 Alkyl-C(O)-, C1-C 10 Alkyl-OC(O)-, C6-C 10 Aryl, C6-C 10 Aryl-O-, C6-C 10 Aryl-C(O)-, C6-C 10 Aryl-OC(O)-; each R a They are the same or different, and are independently selected from halogens, C1-C. 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 cycloalkyl, halogenated C3-C 10 cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, halogenated C3-C 10 At least one of cycloalkyl-O-; R7 is selected from halogens, unsubstituted, or optionally surrounded by one, two, or more R7 groups. b The following groups are substituted: C1-C 10 Alkoxy, C3-C 10 Cycloalkyl-O-, C6-C 10 Aryl, 3-10 quinone heteroaryl; each R b They are the same or different, and are independently selected from halogens, C1-C. 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 cycloalkyl, halogenated C3-C 10 cycloalkyl, C1-C 10 Alkoxy, halogenated C1-C 10 Alkoxy, halogenated C3-C 10 At least one of cycloalkyl-O-; X is selected from C(O)O, unsubstituted or R-substituted. c Substituted C(O)NH;R c Selected from C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 cycloalkyl, halogenated C3-C 10 At least one of the cycloalkyl groups.

2. The compound according to claim 1, its stereoisomers, racemates, tautomers, nitrides, or pharmaceutically acceptable salts, characterized in that, R1, R2, R3, R4, R5, and R6 may be the same or different, and are independently selected from hydrogen, halogen, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 alkoxy, halogenated C1-C6 alkyl, halogenated C3-C8 cycloalkyl, and halogenated C1-C6 alkoxy.

3. The compound according to claim 1 or 2, its stereoisomer, racemate, tautomer, nitride, or pharmaceutically acceptable salt, characterized in that, R1 is selected from halogenated C1-C3 alkyl groups, such as trifluoromethyl; Preferably, R2 is selected from C1-C3 alkyl groups, such as methyl; Preferably, R3 is selected from halogens, such as F; Preferably, R4 is H; Preferably, R5 is selected from halogens, such as Cl; Preferably, R6 is H; Preferably, R7 is selected from unsubstituted or optionally substituted by one, two or more R7s. b Substituted 5-6 membered heteroaryl groups (e.g., thiadiazolyl); each R b They may be the same or different, and are independently selected from C1-C6 alkyl groups (e.g., methyl); Preferably, R7 is selected from Preferably, R7 is selected from methylthiadiazole, for example...

4. The compound, its stereoisomer, racemate, tautomer, nitride, or pharmaceutically acceptable salt according to any one of claims 1-3, characterized in that, The compound represented by Formula I is:

5. A method for preparing the compound according to any one of claims 1-4, its stereoisomers, racemates, tautomers, nitrides, or pharmaceutically acceptable salts, comprising the following steps: Compound a reacts with compound b to give the compound shown in formula I; R1, R2, R3, R4, R5, R6, R7 and X each have the definition described in any one of claims 1-4 independently.

6. A pesticide composition comprising at least one of the compounds of Formula I as described in any one of claims 1-4, their stereoisomers, racemates, tautomers, nitrogen oxides, or pharmaceutically acceptable salts thereof as active ingredients.

7. The pesticide composition according to claim 6, characterized in that, The pesticide composition is a herbicide; Preferably, the grass is barnyard grass.

8. Use of one, two or more of the compounds of Formula I according to any one of claims 1-4, their stereoisomers, racemates, tautomers, nitrogen oxides or pharmaceutically acceptable salts thereof as pesticides, such as herbicides.

9. Use of one, two or more of the compounds of Formula I according to any one of claims 1-4, their stereoisomers, racemates, tautomers, nitrogen oxides or pharmaceutically acceptable salts thereof in the preparation of pesticides, such as herbicides.

10. A method of weed control, comprising applying an effective amount of one, two, or more of the compound of formula I according to any one of claims 1-4, its stereoisomers, racemates, tautomers, nitrogen oxides, or pharmaceutically acceptable salts thereof, or applying the pesticide composition to a medium in which crops grow; Preferably, the crop is rapeseed.

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