WO2020006869A1 - Substituted pyrimidinyl formyl oxime derivative, preparation method therefor, herbicidal composition and use thereof - Google Patents

Abstract

The present invention relates to the technical field of pesticides, and particularly relates to a substituted pyrimidinyl formyl oxime derivative represented by general formula I, a preparation method therefor, a herbicidal composition and use thereof. R1 and R2 independently represent H, halogen, cyano, nitro, alkyl, etc. X represents alkyl, alkoxy, etc. Y represents nitro or NR3R4. A represents halogen or amino. B represents hydrogen, halogen, or alkoxy, alkylthio, alkylamino, or dialkylamino with or without halogen substitution. C represents halogen or haloalkyl. Said compound has excellent herbicidal activity and higher crop safety, with especially good selectivity for key crops such as corn and rice.

Description

Substituted pyrimidineformyloxime derivatives, preparation method, herbicidal composition and application thereof Technical field

The invention belongs to the technical field of pesticides, and particularly relates to a substituted pyrimidineformyloxime derivative, a preparation method thereof, a herbicidal composition and application.

Background technique

The control of weeds is a crucial link in the process of achieving efficient agriculture, despite the variety of herbicides on the market, for example, WO2005 / 063721A1, WO2007 / 082076A1, US7863220B2, US7300907B2, US7642220B2 and US7786044B2 disclose certain 6-amino 2-Substituted-pyrimidine-4-carboxylic acid and its derivatives and their use as herbicides. However, due to the growing market, resistance to weeds, the longevity of drugs and the economics of drugs, and the increasing emphasis on the environment, scientists need to continuously research and develop new high-efficiency, safe, economic, and different Herbicide variety of mode of action.

Summary of the invention

The invention provides a substituted pyrimidinylformyloxime derivative, a preparation method thereof, a herbicidal composition, and an application thereof. The compound has excellent herbicidal activity and has higher crop safety, especially for corn, rice, and the like. Crops have established good selectivity.

The technical scheme adopted by the present invention is as follows:

A substituted pyrimidineformyloxime derivative, as shown in Formula I:

among them,

R ₁ and R ₂ independently represent H, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, cycloalkyl, alkoxy, acyloxy, alkylthio, unsubstituted or substituted aromatic , Benzyl, heteroaryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio, and groups represented by the formula -COR ₅ where R ₅ represents an alkyl group, a haloalkane Group, alkenyl, cycloalkyl, alkoxy, alkenyloxy, cycloalkoxy, alkylthio, alkenylthio, cycloalkylthio, unsubstituted or substituted benzyl, aryl, Heteroaryl, aryloxy, heteroaryloxy, arylmethoxy, heteroarylmethoxy, benzylthio, arylthio, heteroarylthio and available alkyl, acyl, acyl Oxy, unsubstituted or substituted aryl, heteroaryl, arylalkyl, heteroarylalkyl substituted amino; or R ₁ and R _{2 are} connected to form a 5- or 6-membered saturated or unsaturated ring;

X represents alkyl, alkoxy, alkylthio, halogen, alkenyl, alkynyl;

Y represents nitro or NR ₃ R ₄ , wherein R ₃ represents H, alkyl, alkenyl or alkynyl optionally substituted with 1-2 R ₁₁ , -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N = CR ₁₇ R ₁₈ , alkylcarbamoyl, dialkylcarbamoyl, trialkylsilyl or dialkylphosphono; R ₄ represents H, optionally 1-2 R ₁₁ substituted alkyl groups or -COR ₁₂ ; or NR ₃ R ₄ represents N = CR ₂₁ NR ₂₂ R ₂₃ , N = CR ₂₄ OR ₂₅ , unsubstituted or 1-2 independently selected from halogen, Alkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl groups are substituted or contain no oxygen or sulfur atoms Or a 5- or 6-membered saturated or unsaturated ring of another nitrogen atom;

Wherein R ₁₁ independently represents halogen, hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl, unsubstituted or substituted aryl, Heteroaryl

R ₁₂ represents H, alkyl, haloalkyl, alkoxy, phenyl, phenoxy or benzyloxy;

R ₁₃ represents H, alkyl, haloalkyl, phenyl, benzyl or CHR ₃₁ C (O) OR ₃₂ ; R ₃₁ represents H, alkyl or alkoxy; R ₃₂ represents H, alkyl or benzyl;

R ₁₄ represents an alkyl group or a halogenated alkyl group;

R ₁₅ represents H, alkyl, formyl, alkyl acyl, haloalkyl acyl, alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl, or benzyloxycarbonyl; R ₁₆ represents H, alkyl;

R ₁₇ represents H, alkyl, unsubstituted or phenyl substituted with 1-3 of halogen, alkyl, or alkoxy; R ₁₈ represents H, alkyl; or N = CR ₁₇ R ₁₈ represents

R ₂₁ and R ₂₄ each independently represent H or an alkyl group;

R ₂₂ and R ₂₃ each independently represent H or an alkyl group; or NR ₂₂ R ₂₃ represents a 5- or 6-membered saturated or unsaturated ring that does not contain or contain an oxygen atom, a sulfur atom, or another nitrogen atom;

R ₂₅ represents an alkyl group;

A represents halogen and amino;

B represents hydrogen, halogen, alkoxy, alkylthio, alkylamino, dialkylamino with or without halogen substitution;

C represents halogen and haloalkyl.

Preferably, R ₁ and R ₂ independently represent H, cyano, C1-C8 alkyl, halo C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy , C1-C8 acyloxy, C1-C8 alkylthio, unsubstituted or substituted aryl, benzyl, heteroaryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio And a group represented by formula -COR ₅ in which R ₅ represents C1-C8 alkyl, halo C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy , C2-C8 alkenyloxy, C3-C8 cycloalkoxy, C1-C8 alkylthio, C2-C8 alkenylthio, C3-C8 cycloalkylthio, unsubstituted or substituted benzyl, Aryl, heteroaryl, aryloxy, heteroaryloxy, arylmethoxy, heteroarylmethoxy, benzylthio, arylthio, heteroarylthio and available C1-C8 Alkyl, C1-C8 acyl, C1-C8 acyloxy, unsubstituted or substituted aryl, heteroaryl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl-substituted amino; The term "substituted" refers to a group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C2-C8 chain Alkenyl, C1- C8 alkylthio, aryl, aryloxy, benzyl, benzyloxy, C1-C8 acyl, C1-C8 acyloxy, C2-C8 alkenyl and available C1-C8 alkyl, aryl, aryl Substituted with one or more groups of alkoxy, C1-C8 acyl, C1-C8 acyloxy and C2-C8 alkenyl substituted amino;

X represents C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, halogen, C2-C8 alkenyl, C2-C8 alkynyl;

Y represents nitro or NR ₃ R ₄ , wherein R ₃ represents H, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, optionally substituted with 1-2 R ₁₁ , -COR ₁₂ , Nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N = CR ₁₇ R ₁₈ , C1-C8 alkylcarbamoyl, di-C1-C8 alkylcarbamoyl, tri-C1-C8 alkylformyl Silane or di-C1-C8 alkylphosphono; R ₄ represents H, C1-C8 alkyl or -COR ₁₂ optionally substituted with 1-2 R ₁₁ ; or NR ₃ R ₄ represents N = CR ₂₁ NR ₂₂ R ₂₃ , N = CR ₂₄ OR ₂₅ , unsubstituted or 1-2 independently selected from halogen, C1-C8 alkyl, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkane Substituted by groups in thio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino, di-C1-C8 alkylamino, C1-C8 alkoxycarbonyl

Where R ₁₁ independently represents halogen, hydroxy, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino , Di-C1-C8 alkylamino, C1-C8 alkoxycarbonyl, unsubstituted or benzene substituted by 1-3 groups in halogen, C1-C8 alkyl, C1-C8 alkoxy, nitro Base, naphthyl,

R ₁₂ represents H, C1-C18 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy, phenyl, phenoxy, or benzyloxy;

R ₁₃ represents H, C1-C8 alkyl, halo C1-C8 alkyl, phenyl, benzyl or CHR ₃₁ C (O) OR ₃₂ ; R ₃₁ represents H, C1-C8 alkyl or C1-C8 alkoxy R ₃₂ represents H, C1-C8 alkyl or benzyl;

R ₁₄ represents C1-C8 alkyl, halogenated C1-C8 alkyl;

R ₁₅ represents H, C1-C8 alkyl, formyl, C1-C8 alkyl acyl, halo C1-C8 alkyl acyl, C1-C8 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl, or benzyloxy Carbonyl; R ₁₆ represents H, C1-C8 alkyl;

R ₁₇ represents H, C1-C8 alkyl, unsubstituted or phenyl substituted by 1-3 of halogen, C1-C8 alkyl, C1-C8 alkoxy; R ₁₈ represents H, C1- C8 alkyl; or N = CR ₁₇ R ₁₈ represents

R ₂₁ and R ₂₄ each independently represent H or C1-C8 alkyl;

R ₂₂ and R ₂₃ each independently represent H or C1-C8 alkyl; or NR ₂₂ R ₂₃ represents

R ₂₅ represents C1-C8 alkyl;

A represents halogen and amino;

B represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, di-C1-C8 alkylamino with or without halogen substitution;

C represents halogen, halogenated C1-C8 alkyl.

In the definitions of the compounds of the general formula given above, the terms used in the compilation are defined as follows:

The aryl groups in the R ₁ and R ₂ groups preferably include a phenyl group, an 2,3-dihydroindenyl group, or a naphthyl group; and the heteroaryl group includes 1-3 O, S, and N heteroatoms. 5- to 10-membered heteroaryl groups such as pyridyl, pyrimidinyl, pyrazinyl, furyl, thienyl, pyrrolyl, pyrazolyl, thiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazole Base, oxadiazolyl, thiadiazolyl, pyridazinyl, triazinyl, quinolinyl, quinoxalinyl, indolyl, benzotriazolyl, benzothienyl, benzofuranyl, iso Quinolinyl, tetrahydroquinolinyl and the like.

More preferably, R ₁ and R ₂ independently represent hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, cyano, C1-C6 alkoxycarbonyl, and unsubstituted or selected Phenyl substituted with one or more of halogen, halogenated C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkoxy, and C2-C6 alkenyl;

X represents C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, halogen, C2-C6 alkenyl, C2-C6 alkynyl;

Y represents nitro or NR ₃ R ₄ , wherein R ₃ represents H, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, optionally substituted by 1-2 R ₁₁ , -COR ₁₂ , Nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N = CR ₁₇ R ₁₈ , C1-C6 alkylcarbamoyl, di-C1-C6 alkylcarbamoyl, tri-C1-C6 alkylformyl Silane or di-C1-C6 alkylphosphono; R ₄ represents H, C1-C6 alkyl or -COR ₁₂ optionally substituted with 1-2 R ₁₁ ; or NR ₃ R ₄ represents N = CR ₂₁ NR ₂₂ R ₂₃ , N = CR ₂₄ OR ₂₅ , unsubstituted or 1-2 independently selected from halogen, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkane Substituted by groups in thio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxycarbonyl

Where R ₁₁ independently represents halogen, hydroxy, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino , Di-C1-C6 alkylamino, C1-C6 alkoxycarbonyl, unsubstituted or benzene substituted by 1-3 of halogen, C1-C6 alkyl, C1-C6 alkoxy, nitro Base, naphthyl,

R ₁₂ represents H, C1-C14 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, phenyl, phenoxy or benzyloxy;

R ₁₃ represents H, C1-C6 alkyl, halo C1-C6 alkyl, phenyl, benzyl or CHR ₃₁ C (O) OR ₃₂ ; R ₃₁ represents H, C1-C6 alkyl or C1-C6 alkoxy R ₃₂ represents H, C1-C6 alkyl or benzyl;

R ₁₄ represents C1-C6 alkyl, halogenated C1-C6 alkyl;

R ₁₅ represents H, C1-C6 alkyl, formyl, C1-C6 alkylacyl, halo C1-C6 alkylacyl, C1-C6 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxy Carbonyl; R ₁₆ represents H, C1-C6 alkyl;

R ₁₇ represents H, C1-C6 alkyl, unsubstituted or phenyl substituted with 1-3 groups of halogen, C1-C6 alkyl, C1-C6 alkoxy; R ₁₈ represents H, C1- C6 alkyl; or N = CR ₁₇ R ₁₈ represents

R ₂₁ and R ₂₄ each independently represent H or C1-C6 alkyl;

R ₂₂ and R ₂₃ each independently represent H or C1-C6 alkyl; or NR ₂₂ R ₂₃ represents

R ₂₅ represents C1-C6 alkyl;

A represents halogen and amino;

B represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, di-C1-C6 alkylamino with or without halogen substitution;

C represents halogen, halogenated C1-C6 alkyl.

More preferably, R ₁ and R ₂ independently represent hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, cyano, C1-C4 alkoxycarbonyl, and unsubstituted or selected Phenyl substituted with one or more of halogen, halogenated C1-C4 alkyl, C1-C4 alkyl, C1-C4 alkoxy, and C2-C4 alkenyl;

X represents C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, halogen, C2-C4 alkenyl, C2-C4 alkynyl;

Y represents nitro or NR ₃ R ₄ , wherein R ₃ represents H, C1-C4 alkyl, C2-C4 alkenyl, or C2-C4 alkynyl, optionally substituted with 1-2 R ₁₁ , -COR ₁₂ , Nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N = CR ₁₇ R ₁₈ , C1-C4 alkylcarbamoyl, di-C1-C4 alkylcarbamoyl, tri-C1-C4 alkylformyl Silane or di-C1-C4 alkylphosphono; R ₄ represents H, C1-C4 alkyl or -COR ₁₂ optionally substituted with 1-2 R ₁₁ ; or NR ₃ R ₄ represents N = CR ₂₁ NR ₂₂ R ₂₃ , N = CR ₂₄ OR ₂₅ , unsubstituted or 1-2 independently selected from halogen, C1-C4 alkyl, C1-C4 alkoxy, halo C1-C4 alkoxy, C1-C4 alkane Substituted by groups in thio, halo C1-C4 alkylthio, amino, C1-C4 alkylamino, di-C1-C4 alkylamino, C1-C4 alkoxycarbonyl

Where R ₁₁ independently represents halogen, hydroxy, C1-C4 alkoxy, halo C1-C4 alkoxy, C1-C4 alkylthio, halo C1-C4 alkylthio, amino, C1-C4 alkylamino , Di-C1-C4 alkylamino, C1-C4 alkoxycarbonyl, unsubstituted or benzene substituted by 1-3 groups of halogen, C1-C4 alkyl, C1-C4 alkoxy, nitro Base, naphthyl,

R ₁₂ represents H, C1-C8 alkyl, halo C1-C4 alkyl, C1-C4 alkoxy, phenyl, phenoxy or benzyloxy;

R ₁₃ represents H, C1-C4 alkyl, halo C1-C4 alkyl, phenyl, benzyl or CHR ₃₁ C (O) OR ₃₂ ; R ₃₁ represents H, C1-C4 alkyl or C1-C4 alkoxy R ₃₂ represents H, C1-C4 alkyl or benzyl;

R ₁₄ represents C1-C4 alkyl, halogenated C1-C4 alkyl;

R ₁₅ represents H, C1-C4 alkyl, formyl, C1-C4 alkylacyl, halo C1-C4 alkylacyl, C1-C4 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxy Carbonyl; R ₁₆ represents H, C1-C4 alkyl;

R ₁₇ represents H, C1-C4 alkyl, unsubstituted or phenyl substituted with 1-3 of halogen, C1-C4 alkyl, C1-C4 alkoxy; R ₁₈ represents H, C1- C4 alkyl; or N = CR ₁₇ R ₁₈ represents

R ₂₁ and R ₂₄ each independently represent H or C1-C4 alkyl;

R ₂₂ and R ₂₃ each independently represent H or C1-C4 alkyl; or NR ₂₂ R ₂₃

R ₂₅ represents C1-C4 alkyl;

A represents halogen and amino;

B represents hydrogen, halogen, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino, di-C1-C4 alkylamino with or without halogen substitution;

C represents halogen, halogenated C1-C4 alkyl.

Further preferably, R ₁ and R ₂ independently represent hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, methylthio, ethylthio, cyano, methoxycarbonyl, ethoxycarbonyl, and unsubstituted or substituted selected from halogen, CF _3, methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, methoxy and b Phenyl substituted with one or more groups in the oxy group;

X represents chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl;

Y represents NH ₂ , NHMe, N (Me) ₂ ,

A represents fluorine, chlorine, and amino;

B represents hydrogen, fluorine, chlorine, methoxy, ethoxy, and methylthio with or without fluorine;

C stands for fluorine, chlorine, and trifluoromethyl.

The preparation method of the substituted pyrimidineformyloxime derivative includes the following steps:

A compound represented by the general formula II is reacted with a compound represented by the general formula III to prepare a compound represented by the general formula I. The reaction equation is as follows:

The reaction is performed in an aprotic solvent under the action of a base and a condensing agent.

The reaction temperature is from 0 ° C to 90 ° C, preferably from 25 ° C to 30 ° C.

The solvent is selected from one of dichloromethane, dichloroethane, acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene, and xylene. One or more mixed solvents.

The base is selected from one or more of organic bases such as triethylamine, trimethylamine, DIPEA, and DBU.

The condensing agent is PyBop, HATU or HOBt-EDCI.

A herbicide composition comprising a herbicidally effective amount of at least one of said substituted pyrimidineformyloxime derivatives.

The herbicide composition further includes a formulation aid.

A method for controlling harmful plants, comprising using a herbicidally effective amount of at least one of said substituted pyrimidineformyloxime derivatives or said herbicide composition on plants or harmful plant areas.

Use of at least one of the substituted pyrimidineformyloxime derivatives or the herbicide composition for controlling harmful plants.

Preferably, the substituted pyrimidineformyloxime derivative is used for controlling harmful plants in useful crops.

More preferably, the useful crop is a transgenic crop or a crop processed by genome editing technology.

For many economically important monocotyledonous and dicotyledonous harmful plants, the compounds of the formula I according to the invention have outstanding herbicidal activity. The active substance of the present invention is also effective for perennial weeds, which are grown from rhizomes, rhizomes, or other perennial organs and are difficult to control. In this regard, it is generally not important whether the substance is used before sowing, before or after germination. Special mention is made of representative examples of monocotyledonous and dicotyledonous weed populations that can be controlled by the compounds of the present invention, without being limited to certain identified species. Examples of weed species for which the active substance is effective include monocotyledonous plants: annual oats, rye, grasses, spectrums, ferraris, cormorants, tangs, foxtails and sedges, and perennial ice Puccinellia, Cynodon dactylona, Puccinellia and Sorghum, and perennial sedge.

Regarding dicotyledonous weed species, species whose effects can be extended to, for example, annual Hogweed, Viola, Porona, wild sesame, Stellaria, Polygonum, White mustard, Ipomoea, Saffron Genus, Matricaria and Ramie, and Perennial Weed Convolvulus, Thistle, Rumex and Artemisia. The active substance of the present invention effectively controls harmful plants, such as loquat, Cigurus, Alisma, Polygonum, canegrass and sedge, under the undetermined conditions of rice seeding. If the compound of the present invention is applied to the soil surface before germination, the seedlings of weeds can be completely prevented before weeds grow, or the weeds can stop growing when weeds develop cotyledons, and finally die completely after three to four weeks. The compounds of the present invention are particularly active against plants such as Apila, small sesame, Curcuma sibiricum, Stellaria, ivy leaf, Porvana, Arabian Porvana, Pansy and Loquat, Galium .

Although the compound of the present invention has excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, it does not cause any damage to important economic crop plants such as wheat, barley, rye, rice, corn, sugar beet, cotton, and soybean Or, the damage is trivial. Especially compatible with cereal crops, such as wheat, barley and corn, especially wheat. Therefore, the compounds of the present invention are very suitable for selectively controlling unwanted plants in agricultural or ornamental plants.

Due to their herbicidal properties, these active substances can be used to control harmful plants in the cultivation of genetically engineered plants that are known or will emerge. Transgenic plants generally have superior traits, such as resistance to specific pesticides, particularly herbicides, resistance to plant diseases or pathogenic microorganisms of plant diseases, such as specific insect or fungal, bacterial or viral microorganisms. Other special traits are related to the following conditions of the product, such as quantity, quality, storage stability, components and special ingredients. As such, it has been known that the obtained transgenic plant products have increased starch content or improved starch quality or different fatty acid components.

The compounds of the formula I or their salts according to the invention are preferably used in economically important genetically modified crops and ornamental plants, such as cereals, such as wheat, barley, rye, oats, millet, rice, cassava and corn, or in beets, Cultivation of cotton, soybean, rapeseed, potato, tomato, pea and other vegetable plants. The compounds of the formula I are preferably used as herbicides for the cultivation of useful plants which are resistant or which are genetically engineered to be toxic to the herbicide.

Traditional methods of breeding plants with improved shapes over known plants include, for example, traditional mating methods and mutant strain breeding. In other words, new plants with improved traits can be obtained by means of genetic engineering methods (see, for example, EP-0221044A, EP-0131624A). For example, several methods have been described:

-In order to improve starch synthesis in plants, genetic engineering is used to alter crop plants (eg WO 92/11376, WO 92/14827, WO 91/19806);

-Transgenic crop plants resistant to specific herbicides, to glufosinate herbicides (e.g. EP-0242236A, EP-0242246A) or to glyphosate herbicides (WO92 / 00377), or Ureide herbicides (EP-0257993A, US-5013659A);

-Transgenic crop plants such as cotton, which are capable of producing Bacillus thuringiensis toxin (Bt toxin), which can protect against plant damage by specific pests (EP-0142924A, EP-0193259A);

-Transgenic crop plants with improved fatty acid composition (WO91 / 13972).

Many molecular biotechnologies capable of producing transgenic plants with improved traits have been known (see, eg, Sambrook et al., 1989, Molecular Amplification, Second Manual of Experiments, Cold Spring Harbor Laboratory, Cold Spring Harbor, New York; or Winnacker "Gene Kund" "[Genes and Clones], VCH Weinheim, Second Edition 1996 or Christou," Trends in Plant Science "1 (1996) 423-431)). In order to realize the operation of genetic engineering, a nucleic acid molecule may be introduced into a plasmid, and mutation or sequence change may occur through recombination of the DNA sequence. Using the standard methods described above, for example, substrates can be exchanged, partial sequences can be removed, or natural or synthetic sequences can be added. In order to connect DNA fragments to each other, it is possible to attach a conjugate or a linker to the fragments.

Plant cells with reduced activity gene products can be prepared, for example, by expressing at least one appropriate antisense-RNA, sense-RNA to achieve co-suppression, or by expressing at least one appropriately constructed ribozyme, It specifically cleaves the transcription products of the aforementioned gene products.

For this purpose, it is possible to use DNA molecules that contain the entire coding sequence of the gene product, including any flanking sequences that may be present, and to use DNA molecules that contain only a portion of the coding sequence, which must be long enough to be antisense in the cell Effect. It is also possible to use sequences that have a high degree of homology to the gene product coding sequence but are not identical.

When expressing a nucleic acid molecule in a plant, the synthesized protein can be localized in any desired plant cell compartment. However, in order to locate in a particular chamber, it is possible, for example, to link the coding region to a DNA sequence to ensure localization at a particular location. These sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992) 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al. Plant J. 1 (1991), 95-106).

Transgenic plant cells can be reconstituted into whole plants using known techniques. The transgenic plant can be any desired plant variety, ie, monocotyledonous and dicotyledonous plants. In this way, it is possible to obtain transgenic plants with improved traits by overexpression, inhibition or suppression of homologous (= natural) genes or gene sequences, or by expression of heterologous (= external) genes or gene sequences.

When the active substance of the present invention is used on genetically modified crops, in addition to having the effect of inhibiting harmful plants that can be observed on other crops, there are often special effects on the corresponding genetically modified crops, for example, the control can be improved or expanded The range of weeds, improved application rates during application, preferably a good combination of the resistance of transgenic crops and the performance of herbicides, and the effect of the growth and yield of transgenic crop plants. The invention therefore also provides the use of said compounds as herbicides to control harmful plants in transgenic crop plants.

In addition, the compounds of the present invention can significantly regulate the growth of crop plants. By regulating participation in plant metabolism, these compounds are used to orient the control of plant components and promote harvesting, such as drying and dwarfing plants. They are also suitable for regulating and inhibiting unwanted plant growth without disrupting crop growth. Inhibiting plant growth plays a very important role in many monocotyledonous and dicotyledonous crops because it can reduce or completely prevent lodging.

The compounds of the present invention can be applied using general formulations, and wettable powders, concentrated emulsions, sprayable solutions, powders, or granules can be used. The invention thus also provides a herbicide composition comprising a compound of formula I. The compounds of formula I can be formulated in a variety of ways depending on the usual biological and / or chemical physical parameters. Examples of suitable formulation choices are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, concentrated emulsions (EC), such as oil-in-water dispersion and water-in-oil dispersion emulsion (EW) Sprayable solutions, suspending agent concentrates (SC), dispersible oil suspending agents (OD), suspensions with oil or water as a diluent, miscible oil solutions, powders (DP), capsule suspensions (CS ), Seed dressing composition, particles for seeding and soil application, spray particles, coated particles and absorbent particles, water-dispersible particles (WG), water-soluble particles (SG), ULV (ultra Low volume) formulations, microcapsules and wax products. These individual formulation types are known and described in the literature such as Winnacker-Küchler, "Chemische Techonologie" [Chemical Process], Volume 7, C. Hauser Verlag Munich, 4th edition 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd edition 1979, G. Goodwin Ltd. London.

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[环氧乙烷加成物表面活性剂]，Wiss.Verlagagesell.Stuttgart 1976；Winnacker-Küchler的“Chemische Technologie”[化学工艺]，第7卷，C.Hauser Verlag Munich，第4版1986。 Necessary formulation auxiliaries such as inert substances, surfactants, solvents and other additives are also known and described in documents such as the "Handbook of Powder Thinner Pesticides and Carriers" by Watkins, Second Edition, Darland Books Caldwell NJ; Hv01phen "Introduction to Clay Colloid Chemistry", Second Edition, J. Wiley and Sons, NY; C. Marsden's "Solvent Guide" Second Edition, Interscience, NY1963; McCutcheon's "Detergents and Emulsifiers" Annual Report ", MC Publishing Company, Ridgewood NJ; Sisley and Wood," Encyclopedia of Surfactants ", Chemical Publishing Company, NY1964;

of

[Ethylene oxide adduct surfactant], Wiss. Verlagagesell. Stuttgart 1976; "Chemische Technologie" by Winnacker-Küchler [Chemical Process], Volume 7, C. Hauser Verlag Munich, 4th edition 1986.

Wettable powders are uniformly dispersible in water. In addition to active materials, they also include diluents or inert materials, ionic and non-ionic surfactants (wetting agents, dispersants), such as polyethoxyalkylphenol, poly Ethoxy fatty alcohols, polyoxyethyl aliphatic amines, fatty alcohol polyglycol ether sulfates, alkyl sulfonates, alkyl phenyl sulfonates, sodium lignosulfonate, 2,2'-dinaphthyl methane Sodium-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleylmethyltaurine. In order to prepare a wettable powder, the active substance of the herbicide is finely milled, for example, using commonly used equipment such as a hammer mill, a fan mill, and an air jet mill, and the additives are mixed simultaneously or sequentially.

Dissolve the active substance in an organic solvent to prepare a concentrated emulsion, such as butanol, cyclohexanone, dimethylformamide, xylene or a mixture of higher boiling aromatic compounds or hydrocarbons or solvents, and add one more One or more ionic and / or non-ionic surfactants (emulsifiers). Examples of emulsifiers that can be used are calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaromatic polyglycol ethers, fatty alcohols Polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters, or polyoxyethylene sorbites such as polyoxyethylene sorbitan fatty acid esters Glycan ester.

The active substance and finely divided solid substance are ground to obtain a powder, such as talc, natural clays such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth. Water- or oil-based suspensions can be prepared by, for example, wet milling using a commercially available glass bead mill, with or without the addition of another type of surfactant as described above.

To prepare an emulsion such as an oil-in-water emulsifier (EW), an aqueous organic solvent may be used, a stirrer, a colloid mill, and / or a static mixer may be used, and if desired, another type of surfactant as described above may be added.

Granules are prepared by the following method, spraying the active material on the adsorbent, granulating it with an inert material, or concentrating the active material on the surface of a carrier such as sand or kaolinite, granulating the inert material with a binder, Mixtures such as polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable actives can be plasmided by the method of preparing fertilizer granules, and if necessary, mixed with fertilizer. Water suspension granules are prepared using common methods, such as spray-drying, fluidized bed granulation, grinding disc granulation, mixing using a high-speed mixer, and extrusion without solid inert materials.

Regarding the preparation method using grinding discs, fluidized beds, extruders and spray granules, please refer to the following processes, for example, "Spray Drying Handbook" 3rd Edition 1979, G. Goodwin Ltd., London; Chemistry and Engineering 1967, p. 147ff; "Engineer's Handbook of Perry's Chemistry", Fifth Edition, McGraw-Hill, New York 1973, pp. 8-57. For information on the formulation of crop protection products, see, for example, GCKlingman, "Weed Control, Science", John Wiley and Sons, New York, pp. 81-96, and JDFreyer, SAEvans "Weed Control Handbook", Fifth Edition, Blackwell Scientific Publications, Oxford University 1968, pp. 101-103.

Agrochemical formulations usually contain from 0.1 to 99%, in particular from 0.1 to 95% by weight of the active substance formula I. The concentration of the active substance in the wettable powder is, for example, from about 10 to 99% by weight, and the usual formulation components constitute the remaining amount to 100% by weight. The concentration of the active substance in the concentrated emulsion may be about 1 to 90% by weight, preferably 5 to 80%. The powder formulation contains 1 to 30% by weight of active substance, usually 5 to 20% by weight of active substance is preferred, however, the sprayable solution contains about 0.05 to 80% by weight, preferably 2 to 50% by weight of active substance . Regarding the content of the active substance in the water-suspended granules, it is mainly based on whether the active substance is liquid or solid, and the auxiliary agent, filler and the like used in granulation. The content of the active substance in the aqueous suspension granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the preparation of the active substance may include a tackifier, a wetting agent, a dispersant, an emulsifier, a penetrant, a preservative, an antifreeze, a solvent, a filler, a carrier, a colorant, a defoamer, an evaporation inhibitor, and PH and viscosity modifiers are commonly used in all cases.

Based on these preparations, it may also be mixed with other pesticide active substances such as pesticides, acaricides, herbicides and fungicides. It may also be mixed with safeners, fertilizers and / or plant growth regulators. The mixing method may be Pre-mixed or filled.

In the compound formulation or tank mix formulation, suitable active substances that can be mixed with the active substance of the present invention are, for example, "World Encyclopedia of New Pesticides and Technologies", China Agricultural Science and Technology Press, 2010.9 and the documents cited here. Known substances. For example, the herbicide active substance mentioned below can be mixed with a mixture of formula I, (note: the name of the compound, or the common name according to the International Organization for Standardization (ISO), or the chemical name, with a code when appropriate): acetochlor Amine, Butachlor, Acetochlor, Mesochloride, Metolachlor, Smetochlor, Prochlortochlor, Toxachlor, Clotrim, Naproxyl, R-L-naphthopro Carbamide, Diazepam, Phenoxybenzamide, Bifentochlor, Piracetamide, Herbachlor, Flubutyramide, Bromobutyramide, Metformamide, High-Efficiency Dimethoxamine Thiachlor, acetochlor, fluoxacil, methachlor, mechlorpyr, clomazone, high-performance dicamba, high-effect dicamba, dipropachlor, dimethoxamine , Butachlor, ciprofen, sulfasalox, heptanosin, isobutachlor, propachlor, terbutachlor, xyloxadi, alachlor, paraquat, Trimethoprim, Chloroform, Acetochlor, Valprofen, Carbamide, Neosalin, Tricyclomethoxamine, Butachlor, Herbachlor, Bentochlor, Quinaclopyramide, fenflurane, naphthylamine, acetochlor, chlorpyramid, thiamethoxam, cyperamide, chlorpyrrolam, chlorpyrrol, chlorthimide, butamidine, flupir Glufosinate, atrazine, simazine, profenazine, cyanurin, chloracetin, fenpronil, fenfluramine, isopropyl, flubuterin, terbutin, terbutin, triazine Amine, ciprofloxacin, ganprezine, cadazine, chlorphenazine, cimatone, azide, dichlordi, isoprene, ciprofloxacin, fenprozine, fenprozine, chlorbutrazine, chlorbutrazine, Terbutin, trimethoprim, cyanuric acid, chlorprothionine, colazine, atrazine, dicamba, glycyrrhizin, cyanuric acid, Indaziflam, chlorsulfuron, metsulfuron, bensulfuron, Chlorimuron-methyl, besulfuron-methyl, thiosulfuron-methyl, pyrimsulfuron-methyl, methylsulfuron-methyl, iodosulfuron-methyl sodium, formylsulfuron-methyl, sulfsulfuron-methyl, trisulfuron-methyl Sulfonuron, Nicosulfuron, Amisulfuron, Sulfsulfuron, Ethoxysulfuron, Ciprosulfuron, Sulfsulfuron, Tetrasulfuron, Pirimisulfuron, Monosulfuron , Monosulfuronate, fluazosulfuron, flusulfuron, flursulfuron Thalamus, triazosulfuron, triazosulfuron, flusulfuron, tribensulfuron, trifluorosulfuron, trisulfuron, triflusulfuron, fluasulfuron, trifluorosulfuron Thalamus, metsulfuron-methyl sodium, flusulfuron-methyl, thimesulfuron-methyl, pyrisulfuron-methyl, propyrisulfuron (prosulfuron), trimethosulfuron-methyl, triflufenacil-methyl, flusulfuron, Lactofazone, acetofluoride, oxyfluorfen, chlorpyrrol, acetochlor, chloroflufenamate, trimethoprim, triflufenachlor, trimethoprim, trimethoprim Flunoxadi, fluorinated herbicide, flufenacil, herbicide, chlorfendi, dimethylchlor, flubendimethoxam, flufenamid, Halosafen, green malon, isopropylon, liqueur Thalon, diuron, safluuron, fluoxauron, benzothalon, methylphenothalon, bensulfuron, sulfsulfuron, isoxuron, terbuturon, acetyluron, clobron, Methylpyrrolidone, acylpyrrolidone, methaluron-methyl, bromogluturon, methalon-methyl, green-growth, chlorfenuron-methyl, cypersulfuron-methyl, non-chlorsulfuron-methyl, thiosulfuron-methyl, chlorsulfuron-methyl, chlorpyron , Calamonone, Isotrione, Cyclopron, Teflon, Butathialone Cumulon, parafluon, methamidazole, chlorpyrrolam, trimethylisourea, oxazolone, monisouron, anisuron, methiuron, chloreturon, tetrafluron, betaine, betaine-ethyl, betaine, sulfonate Herbaspirin, Tetrasperam, Oatrin, Aniline, Chloraniline, Dicloxacil, Herbazone, Chlorhexim, Carboxazole, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, Butachlor, Herbazone , Herbicide Meng, Hecaote, Yemaiwei, Piperacetam, Chrysoperia, Scopolamine, Ringgrass, Oatmeal, Bactarime, Ethylthiopyr, Pingcaodan, Kecaomen, Bengal Dan, Zhongcao Dan, Thiamethazone, Grass Disinfection, Isopolinate, Methiobencarb, 2,4-Dibutyl Butyl, 2 Methyl Chlorochloride, 2,4-Disooctyl Ester, 2 Methyl Chloroisooctyl Ester, 2,4-D sodium salt, 2,4-Ddimethylamine salt, 2M-4chloroethylthioester, 2M-4chloro, 2,4-DPA propionic acid, high 2,4-DPA propionate, 2 , 4-dibutyric acid, 2 methyl 4 chloropropionic acid, 2 methyl 4 chloropropionic acid salt, 2 methyl 4 chlorobutanoic acid, 2,4,5-dipyridine, 2,4,5-diphenylpropionic acid, 2,4 , 5-Abbutyric acid, 2 methyl 4 chloramine salt, dicamba, chloramphenicol, valeric, saison, trichlorobenzoic acid, ammonia dichlorobenzoic acid Methoxytrichlorobenzoic acid, grass herb, pilofluoxin, fine fluoxazoline, flumecloxazone, high-efficiency flucloxazone, quinoxaline, finequinoxaline, oxazole grass Aspirin, oxadiazine, oxadiazate, cyflumetazone, oxazosin, acetochlor, thiazoline, oxadiazine, valprofen, trifluoxame, isoxamine Paracetamol, Paraquat, Diquat, Disulfiram, Ebutenylfluoxin, Isoproline, Mesosulfurin, Ciprofloxacin, Amiprofloxacin, Ebutylfluoxin, Chlorethalin, Aminethalin, dilorin, chlorethalin, Methalpropalin, propranol, glyphosate, salinate, glufosinate, methylglyphosate, glufosinate, piperidin, dipropionamine Phosphine, Diphosphine, Proton, Phytophosphine, Valprofen, Dimethoate, Zytophos, Imidazosin, Imidazosin, Imidazoquinoic Acid, Mimibutazone, Metosalamide Salt, memidazole nicotinic acid, imazamox, fenfluroxyacetic acid, isooctyl clofloxypyroxyacetic acid, dichloropyridic acid, amlpicolinic acid, trichloropyroxyacetic acid, fluoxurn, and fluoxadine , Trichloropyridine, thiachlor, Fluoxastrone, chlorampiric acid, flufenazone, butoxyethyl trichloropyroxyacetate, Cliodinate, oxadiazine, clethodim, acetochlor, acetochlor, cyprobenone, butanone Bentophenone, oxamethone, pyracone, Buthidazole, oxadiazon, cyprodone, oxazone, acetazinone, Ametridione, Amibuzin, bromobenzonitrile, caprylyl benzonitrile, caprylyl iodide Benzonitrile, iodobenzonitrile, dipropionitrile, diphenylacetonitrile, bisoxadipyrazole, hydroxydipropoxynil, Iodobonil, saflufenacil, diflufenacil, pentosufuracil, sulfachlor, Chlorsulfuron, mesotrichlor, saflufenacil, fluroxypyr, acetochlor, pyrimoxifen, ciprofen, acetochlor, sulfamethoxam, disulfatrione, nitrate Sulcotrione, sulcotrione, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, isoxaflutole, isoxaflutole, Fenoxasulfone, Methiozolin, ipraprofen, proxafen, pyrazol, yew, Benpropazone, imazethone, chlorflume, Pyrasulfotole, oxafludizone, Pyroxasulfone, fluoxadi, fluoxadi, flufenazone, fenoxazone, oxadiazon, amidazol Humulone, flufenazone, mesotrione, Bencarbazone, diflufenazone, fluroxypyr, chlorfendizone, isotridime, cyclamidine, trimethoprim, Flupropacil, indoxazone, Flufenoxal, propoxyflutochlor, flufenoxamine, phthalyl benzyl ether, Flumezin, pentachlorophenol (sodium), deloxyl, trisphenol, trisyl ester, pentosin, dinitrosin, chlorinol , Diloxif, Dilote, propynoxazone, oxadiazone, cyclopentazone, fluoxachlor, methyloxazine, methyltetrazolidin, flupyridoxazone, fenoxaben , Bromopyramine, dimethylpyridoxine, pyridazol, chlorpyridone, chlorpyrazine, pypyridoxine, Pyridafol, dicloquinac, chloroquinolinic acid, bentazon, pyridoxet, oxazine Herbazone, Herbazone, clomazone, cycloheptazone, isopropylacetazone, propylazone, indone, sodium chlorate, prawn, trichloroacetic acid, monochloroacetic acid, hexachloroacetone , Tetrafluoropropionic acid, forage herb, bromophenol oxime, triazosul, mefenzole, furazone, furasulfa, acetofurazone, fluoxazone, chlorophthalic acid, flunone, humulone , Acrolein, fenben, herbicidal ring, oat ester Thiadiazolamide, gostigmine, oxymethofen, methoxyphenone, saflufenacil, chloralphos-methyl, trichloropropionic acid, Alorac, Diethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, Methiosulfur, Cambendichlor, Ciprofloxacin, Thioaniline, Herbazone, Herbazone, Herbazone, Herbazone, Herbaquine, Herbachlor Alkane, acetochlor, acetochlor, acetochlor, acetofurate, oxatofuran, oxime, bisoxoxalic acid, dichloropropenylamine, chlorochloropyridyl ester, DOW chlorofluridyl ester, UBH 509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO535, DK-8910, V-53482, PP-600, MBH-001 , KIH-9201, ET-751, KIH-6127, and KIH-2023.

When used, commercially available formulations are diluted, if necessary, in the usual manner, such as with wettable powders, concentrated emulsions, suspensions and particles suspended in water, with water. Powders, granules used for soil application, or spraying and spraying solutions generally do not require further dilution with inert substances before use. As the external conditions change, the required amount of the compound of formula I is also different. The external conditions are, for example, temperature, humidity, the nature of the herbicide used, and the like. It can have large variations, for example between 0.001 and 1.0 kg / ha, or more active substances, but preferably between 0.005 and 750 g / ha, especially between 0.005 and 250 g / ha.

detailed description

The following examples are provided to illustrate the invention and should not be construed as limiting the invention in any way. The scope of rights claimed in the present invention is described by the claims.

In view of the economics and diversity of the compounds, we have preferably synthesized some compounds. Among the many compounds synthesized, selected ones are listed in Table 1 below. The specific compound structure and corresponding compound information are shown in Table 1-2. The compounds in Table 1 are only used to better illustrate the present invention, but not to limit the present invention. For those skilled in the art, it should not be understood that the scope of the above subject of the present invention is limited to the following compounds.

Table 1 Compound structure

Table 2 Compound ¹ HNMR data

Examples of representative compounds are as follows:

1. Preparation of compound 98:

Construction of the device: 50mL round bottom single-necked flask, stir bar, constant temperature stirrer.

Compound 8 (0.4 g, 1.2 mmol, 1.0 eq), PyBOP (0.69 g, 1.32 mmol, 1.1 eq), Et ₃ N (0.16 g, 1.6 mmol, 1.3 eq) were sequentially added to 8 ml of DCM and stirred at room temperature. After 30 min, compound b (0.16 g, 1.3 mmol, 1.1 eq) was added, and the reaction solution was stirred for 12 hours. TLC detection, the reaction is complete. The reaction solution was poured into 10 ml of water and the layers were separated. The aqueous phase was extracted three times with 10 ml of DCM. The organic phase was dried, spin-dried, and separated by column chromatography to obtain compound 98 (0.35 g, 67% yield) (white solid).

2. Preparation of compound 99:

Construction of the device: 50mL round bottom single-necked flask, stir bar, constant temperature magnetic stirrer.

In 10 ml of ACN, compound a (0.4 g, 1.2 mmol, 1.0 eq), HATU (0.50 g, 1.32 mmol, 1.1 eq), DBU (0.24 g, 1.6 mmol, 1.3 eq) were sequentially added and stirred at room temperature for 30 min. Compound c (0.15 g, 1.3 mmol, 1.1 eq) was added, and the reaction solution was stirred for 12 hours. TLC detection, the reaction is complete. The reaction solution was poured into 10 ml of water and separated. The aqueous phase was extracted three times with 10 ml of ethyl acetate. The organic phase was dried, spin-dried, and separated by column chromatography to obtain compound 99 (0.38 g, 74% yield) (white solid). .

Several methods of preparing the compounds of the invention are illustrated in the following schemes and examples. The starting materials can be purchased on the market or can be prepared by methods known in the literature or as shown in the detailed description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although the specific raw materials and conditions in the synthetic route have been described below, they can be easily replaced with other similar raw materials and conditions, such as the compounds produced by the modification or variation of the preparation method of the present invention. Various isomers and the like are included in the scope of the present invention. In addition, the preparation method described below can be further modified according to the present disclosure using conventional chemical methods well known to those skilled in the art. For example, appropriate groups are protected during the reaction, and the like.

The method examples provided below are used to promote a further understanding of the preparation method of the present invention. The specific substances, types, and conditions used are determined to further explain the present invention, and are not intended to limit the reasonable scope thereof. The reagents used in the synthetic compounds indicated in the table below are either commercially available or can be easily prepared by one of ordinary skill in the art.

Examples of representative compounds are as follows:

Evaluation of biological activity:

The activity level criteria for harmful plant destruction (i.e. growth control rate) are as follows:

Level 10: Complete death;

Level 9: The growth control rate is above 95%;

Level 8: The growth control rate is above 90%;

Level 7: Growth control rate is above 80%;

Level 6: Growth control rate is above 70%;

Level 5: Growth control rate is above 60%;

Level 4: Growth control rate is above 50%;

Level 3: Growth control rate is above 20%;

Level 2: Growth control rate is 5-20%;

Level 1: Growth control rate is below 5%;

Level 0: No effect.

The above growth control rate is the fresh weight control rate.

Post-emergence test experiment: monocotyledonous and dicotyledonous weed seeds and main crop seeds (wheat, corn, rice, soybean, cotton, rape, millet, sorghum) are placed in plastic pots filled with soil, and then covered with 0.5-2 Centimeters of soil to grow in a good greenhouse environment, test plants are treated at the 4-5 leaf stage after 2-3 weeks of sowing, the test compound of the invention is dissolved with acetone, and then Tween 80 is added. Water is diluted to a certain concentration and sprayed onto plants with a spray tower. After being applied in the greenhouse for 3 weeks, the experimental effects of weeds after 3 weeks are listed in Table 3-4.

Table 3. Post-emergence weed tests

Compound number Artemisia sojae Pig Ramie Aunt Yeci Hydra 1 10 10 10 10 10 2 10 10 10 10 10 3 10 10 10 10 10 4 10 10 10 10 10 5 10 10 10 10 10 6 10 10 10 10 10 7 10 10 10 10 10 8 10 10 10 10 10

9 10 10 10 10 10 10 10 10 10 10 10 11 10 10 10 10 10 12 10 10 10 10 10 13 10 10 10 10 10 14 10 10 10 10 10 15 10 10 10 10 10 16 10 10 10 10 10 17 10 10 10 10 10 18 10 10 10 10 10 19 10 10 10 10 10 20 10 10 10 10 10 twenty one 10 10 10 10 10 twenty two 10 10 10 10 10 twenty three 10 10 10 10 10 twenty four 10 10 10 10 10 25 10 10 10 10 10 26 10 10 10 10 10 27 10 10 10 10 10 28 10 10 10 10 10 29 10 10 10 10 10 30 10 10 10 10 10 31 10 10 10 10 10 32 10 10 10 10 10 33 10 10 10 10 10 34 10 10 10 10 10 35 10 10 10 10 10 36 10 10 10 10 10 37 10 10 10 10 10 38 10 10 10 10 10 39 10 10 10 10 10

40 10 10 10 10 10 41 10 10 10 10 10 42 10 10 10 10 10 43 10 10 10 10 10 44 10 10 10 10 10 45 10 10 10 10 10 46 10 10 10 10 10 47 10 10 10 10 10 48 10 10 10 10 10 49 10 10 10 10 10 50 10 10 10 10 10 51 10 10 10 10 10 52 10 10 10 10 10 53 10 10 10 10 10 54 10 10 10 10 10 55 10 10 10 10 10 56 10 10 10 10 10 57 10 10 10 10 10 58 10 10 10 10 10 59 10 10 10 10 10 60 10 10 10 10 10 61 10 10 10 10 10 62 10 10 10 10 10 63 10 10 10 10 10 64 10 10 10 10 10 65 10 10 10 10 10 66 10 10 10 10 10 67 10 10 10 10 10 68 10 10 10 10 10 69 10 10 10 10 10 70 10 10 10 10 10

71 10 10 10 10 10 72 10 10 10 10 10 73 10 10 10 10 10 74 10 10 10 10 10 75 10 10 10 10 10 76 10 10 10 10 10 77 10 10 10 10 10 78 10 10 10 10 10 79 10 10 10 10 10 80 10 10 10 10 10 81 10 10 10 10 10 82 10 10 10 10 10 83 10 10 10 10 10 84 10 10 10 10 10 85 10 10 10 10 10 86 10 10 10 10 10 87 10 10 10 10 10 88 10 10 10 10 10 89 10 10 10 10 10 90 10 10 10 10 10 91 10 10 10 10 10 92 10 10 10 10 10 93 10 10 10 10 10 94 10 10 10 10 10 95 10 10 10 10 10 96 10 10 10 10 10 97 10 10 10 10 10 98 10 10 10 10 10 99 10 10 10 10 10 100 10 10 10 10 10 101 10 10 10 10 10

102 10 10 10 10 10 103 10 10 10 10 10 104 10 10 10 10 10 Control Compound A 6 4 5 5 6

Note: The application dose is 45 g / ha of the active ingredient and 450 kg / ha.

(来自专利CN102675218B)。 Control Compound A:

(From patent CN102675218B).

Table 4 Post-emergence weed tests

Serial number corn Rice Aunt Yeci Mother-in-law Amaranth Thousands of gold Yarrow 9 1 1 10 10 6 7 10 99 1 1 10 10 7 8 10 Control Compound A 3 2 5 3 6 2 3 Control Compound B 8 5 10 9 3 5 8 Control Compound C 7 5 10 2 2 3 8

Note: The application dose is 30 g / ha of active ingredient and 450 kg / ha.

对照化合物C：氟氯吡啶酯。 Control Compound B:

Control compound C: chlorochloropyridine.

As can be seen from Tables 3 and 4, compared with the control compounds, the compounds of the present invention significantly improve crop safety and herbicidal activity by changing the parent ring structure, substituents, and carboxy derivative types, especially for corn, rice, etc. The key crops have established good selectivity, while the control compound has poor selectivity to main crops. It can be seen that the present invention has achieved excellent technical effects.

Pre-emergence test experiment:

Place monocotyledonous and dicotyledonous weed seeds and main crop seeds (wheat, corn, rice, soybean, cotton, rape, millet, sorghum) in plastic pots filled with soil, and then cover 0.5-2 cm of soil. The test compound of the present invention was dissolved with acetone, then Tween 80 was added, and the solution was diluted with a certain water to a certain concentration solution, and sprayed immediately after sowing. After being applied in the greenhouse for 4 weeks, the experimental results were observed after 3 weeks. It was found that most of the medicaments of the present invention had an excellent effect under the measurement of 250 g / ha, especially for weeds such as yarrow, matang, ramie, and many compounds. Good selectivity for corn, wheat, rice, soybean, rape.

Through experiments, we found that the compounds of the present invention generally have better weed control effects, especially for major weeds such as weeds, tangs, tangs, and ramie, which are widespread in corn fields, rice fields, and wheat fields. , Broadleaf, amaranth and other broadleaf weeds have good effects and good commercial value. In particular, we have noticed that the broad-leaved weeds, such as Amaranth, Sophora pallidum, Amaranth, Maijiagong, Zhuyuan, Stellaria, etc., which are resistant to ALS inhibitors, have extremely high activity.

Evaluation of safety of transplanted rice and evaluation of weed control in paddy field:

After filling the paddy field soil in 1 / 1,000,000 hectare pots, the seeds of yarrow, firefly, wolf grass, and wild auntie were sown, and the soil was gently covered thereon. Thereafter, it was placed in a greenhouse with a water storage depth of 0.5-1 cm, and the tubers of Ye Cigu were implanted the next day or two days later. After that, the water storage depth was kept at 3-4 cm, and the wettability of the compound of the present invention will be adjusted according to the usual preparation method at the time point when the yarrow, firefly, wolfgrass reaches 0.5 leaves, and the wild leaf aunt reaches the primary leaf stage. The water or diluted solution of the powder or suspension is uniformly dropped with a pipette to achieve a predetermined amount of effective ingredients.

In addition, after paddy field soil was filled in 1 / 1,000,000 hectare pots, the soil was leveled to a depth of 3-4 cm, and rice (japonica rice) at the 3-leaf stage was transplanted at a transplant depth of 3 cm the next day. On the 5th day after transplantation, the compound of the present invention was treated in the same manner as described above.

Observe the reproductive status of yarrow, firefly, wolf grass, and wild auntie on the 14th day after treatment with the naked eye, and the reproductive status of rice on the 21st day after treatment. The compounds show excellent activity and selectivity.

Note: The seeds of Yarrow, Firefly, Yeci, and Wolf are all collected from Heilongjiang, China, and have been tested for resistance to conventional doses of pyrimisulfuron.

At the same time, after many tests, it was found that many of the compounds of the present invention have good selectivity for grasses such as zoysiagrass, Cynodon dactylon, tall fescue, bluegrass, ryegrass, seashore paspalum and can prevent many key grasses. Weeds and broadleaf weeds. Tests on soybean, cotton, oil sunflower, potato, fruit tree, and vegetables under different application methods also show excellent selectivity and commercial value.

Claims (10)

A substituted pyrimidineformyloxime derivative, as shown in Formula I:

among them, R ₁ and R ₂ independently represent H, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, cycloalkyl, alkoxy, acyloxy, alkylthio, unsubstituted or substituted aromatic , Benzyl, heteroaryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio, and groups represented by the formula -COR ₅ where R ₅ represents an alkyl group, a haloalkane Group, alkenyl, cycloalkyl, alkoxy, alkenyloxy, cycloalkoxy, alkylthio, alkenylthio, cycloalkylthio, unsubstituted or substituted benzyl, aryl, Heteroaryl, aryloxy, heteroaryloxy, arylmethoxy, heteroarylmethoxy, benzylthio, arylthio, heteroarylthio and available alkyl, acyl, acyl Oxy, unsubstituted or substituted aryl, heteroaryl, arylalkyl, heteroarylalkyl substituted amino; or R ₁ and R _{2 are} connected to form a 5- or 6-membered saturated or unsaturated ring; X represents alkyl, alkoxy, alkylthio, halogen, alkenyl, alkynyl; Y represents nitro or NR ₃ R ₄ , wherein R ₃ represents H, alkyl, alkenyl or alkynyl optionally substituted with 1-2 R ₁₁ , -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N = CR ₁₇ R ₁₈ , alkylcarbamoyl, dialkylcarbamoyl, trialkylsilyl or dialkylphosphono; R ₄ represents H, optionally 1-2 R ₁₁ substituted alkyl groups or -COR ₁₂ ; or NR ₃ R ₄ represents N = CR ₂₁ NR ₂₂ R ₂₃ , N = CR ₂₄ OR ₂₅ , unsubstituted or 1-2 independently selected from halogen, Alkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl groups are substituted or contain no oxygen or sulfur atoms Or a 5- or 6-membered saturated or unsaturated ring of another nitrogen atom; Wherein R ₁₁ independently represents halogen, hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl, unsubstituted or substituted aryl, Heteroaryl R ₁₂ represents H, alkyl, haloalkyl, alkoxy, phenyl, phenoxy or benzyloxy; R ₁₃ represents H, alkyl, haloalkyl, phenyl, benzyl or CHR ₃₁ C (O) OR ₃₂ ; R ₃₁ represents H, alkyl or alkoxy; R ₃₂ represents H, alkyl or benzyl; R ₁₄ represents an alkyl group or a halogenated alkyl group; R ₁₅ represents H, alkyl, formyl, alkyl acyl, haloalkyl acyl, alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl, or benzyloxycarbonyl; R ₁₆ represents H, alkyl; R ₁₇ represents H, alkyl, unsubstituted or phenyl substituted with 1-3 of halogen, alkyl, or alkoxy; R ₁₈ represents H, alkyl; or N = CR ₁₇ R ₁₈ represents

R ₂₁ and R ₂₄ each independently represent H or an alkyl group; R ₂₂ and R ₂₃ each independently represent H or an alkyl group; or NR ₂₂ R ₂₃ represents a 5- or 6-membered saturated or unsaturated ring that does not contain or contain an oxygen atom, a sulfur atom, or another nitrogen atom; R ₂₅ represents an alkyl group; A represents halogen and amino; B represents hydrogen, halogen, alkoxy, alkylthio, alkylamino, dialkylamino with or without halogen substitution; C represents halogen and haloalkyl. The substituted pyrimidineformyloxime derivative according to claim 1, wherein: R ₁ and R ₂ independently represent H, cyano, C1-C8 alkyl, halo C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1- C8 acyloxy, C1-C8 alkylthio, unsubstituted or substituted aryl, benzyl, heteroaryl, aryloxy, arylthio, heteroaryloxy and heteroarylthio, and A group represented by the formula -COR ₅ , wherein R ₅ represents a C1-C8 alkyl group, a halogenated C1-C8 alkyl group, a C2-C8 alkenyl group, a C3-C8 cycloalkyl group, a C1-C8 alkoxy group, C2 -C8 alkenyloxy, C3-C8 cycloalkoxy, C1-C8 alkylthio, C2-C8 alkenylthio, C3-C8 cycloalkylthio, unsubstituted or substituted benzyl, aryl, Heteroaryl, aryloxy, heteroaryloxy, arylmethoxy, heteroarylmethoxy, benzylthio, arylthio, heteroarylthio and available C1-C8 alkyl, C1-C8 acyl, C1-C8 acyloxy, unsubstituted or substituted aryl, heteroaryl, aryl C1-C8 alkyl, heteroaryl C1-C8 alkyl substituted amino; wherein, the "substituted "" Means being selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C2-C8 alkenyloxy C1-C8 alkylthio Aryl, aryloxy, benzyl, benzyloxy, C1-C8 acyl, C1-C8 acyloxy, C2-C8 alkenyl and available C1-C8 alkyl, aryl, aryloxy, C1 -One or more of C8 acyl, C1-C8 acyloxy and C2-C8 alkenyl substituted amino; X represents C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, halogen, C2-C8 alkenyl, C2-C8 alkynyl; Y represents nitro or NR ₃ R ₄ , wherein R ₃ represents H, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl, optionally substituted with 1-2 R ₁₁ , -COR ₁₂ , Nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N = CR ₁₇ R ₁₈ , C1-C8 alkylcarbamoyl, di-C1-C8 alkylcarbamoyl, tri-C1-C8 alkylformyl Silane or di-C1-C8 alkylphosphono; R ₄ represents H, C1-C8 alkyl or -COR ₁₂ optionally substituted with 1-2 R ₁₁ ; or NR ₃ R ₄ represents N = CR ₂₁ NR ₂₂ R ₂₃ , N = CR ₂₄ OR ₂₅ , unsubstituted or 1-2 independently selected from halogen, C1-C8 alkyl, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkane Substituted by groups in thio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino, di-C1-C8 alkylamino, C1-C8 alkoxycarbonyl

Where R ₁₁ independently represents halogen, hydroxy, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino , Di-C1-C8 alkylamino, C1-C8 alkoxycarbonyl, unsubstituted or benzene substituted by 1-3 groups in halogen, C1-C8 alkyl, C1-C8 alkoxy, nitro Base, naphthyl,

R ₁₂ represents H, C1-C18 alkyl, halo C1-C8 alkyl, C1-C8 alkoxy, phenyl, phenoxy, or benzyloxy; R ₁₃ represents H, C1-C8 alkyl, halo C1-C8 alkyl, phenyl, benzyl or CHR ₃₁ C (O) OR ₃₂ ; R ₃₁ represents H, C1-C8 alkyl or C1-C8 alkoxy R ₃₂ represents H, C1-C8 alkyl or benzyl; R ₁₄ represents C1-C8 alkyl, halogenated C1-C8 alkyl; R ₁₅ represents H, C1-C8 alkyl, formyl, C1-C8 alkylacyl, halo C1-C8 alkylacyl, C1-C8 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl, or benzyloxy Carbonyl; R ₁₆ represents H, C1-C8 alkyl; R ₁₇ represents H, C1-C8 alkyl, unsubstituted or phenyl substituted by 1-3 of halogen, C1-C8 alkyl, C1-C8 alkoxy; R ₁₈ represents H, C1- C8 alkyl; or N = CR ₁₇ R ₁₈ represents

R ₂₁ and R ₂₄ each independently represent H or C1-C8 alkyl; R ₂₂ and R ₂₃ each independently represent H or C1-C8 alkyl; or NR ₂₂ R ₂₃ represents

R ₂₅ represents C1-C8 alkyl; A represents halogen and amino; B represents hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, di-C1-C8 alkylamino with or without halogen substitution; C represents halogen, halogenated C1-C8 alkyl. The substituted pyrimidineformyloxime derivative according to claim 1 or 2, characterized in that: R ₁ and R ₂ independently represent hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, cyano, C1-C6 alkoxycarbonyl, and are unsubstituted or selected from halogen, halogen Phenyl substituted with one or more of C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkoxy, and C2-C6 alkenyl; X represents C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, halogen, C2-C6 alkenyl, C2-C6 alkynyl; Y represents nitro or NR ₃ R ₄ , wherein R ₃ represents H, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl, optionally substituted by 1-2 R ₁₁ , -COR ₁₂ , Nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N = CR ₁₇ R ₁₈ , C1-C6 alkylcarbamoyl, di-C1-C6 alkylcarbamoyl, tri-C1-C6 alkylformyl Silane or di-C1-C6 alkylphosphono; R ₄ represents H, C1-C6 alkyl or -COR ₁₂ optionally substituted with 1-2 R ₁₁ ; or NR ₃ R ₄ represents N = CR ₂₁ NR ₂₂ R ₂₃ , N = CR ₂₄ OR ₂₅ , unsubstituted or 1-2 independently selected from halogen, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkane Substituted by groups in thio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino, di-C1-C6 alkylamino, C1-C6 alkoxycarbonyl

Where R ₁₁ independently represents halogen, hydroxy, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino , Di-C1-C6 alkylamino, C1-C6 alkoxycarbonyl, unsubstituted or benzene substituted by 1-3 of halogen, C1-C6 alkyl, C1-C6 alkoxy, nitro Base, naphthyl,

R ₁₂ represents H, C1-C14 alkyl, halo C1-C6 alkyl, C1-C6 alkoxy, phenyl, phenoxy or benzyloxy; R ₁₃ represents H, C1-C6 alkyl, halo C1-C6 alkyl, phenyl, benzyl or CHR ₃₁ C (O) OR ₃₂ ; R ₃₁ represents H, C1-C6 alkyl or C1-C6 alkoxy R ₃₂ represents H, C1-C6 alkyl or benzyl; R ₁₄ represents C1-C6 alkyl, halogenated C1-C6 alkyl; R ₁₅ represents H, C1-C6 alkyl, formyl, C1-C6 alkylacyl, halo C1-C6 alkylacyl, C1-C6 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxy Carbonyl; R ₁₆ represents H, C1-C6 alkyl; R ₁₇ represents H, C1-C6 alkyl, unsubstituted or phenyl substituted with 1-3 groups of halogen, C1-C6 alkyl, C1-C6 alkoxy; R ₁₈ represents H, C1- C6 alkyl; or N = CR ₁₇ R ₁₈ represents

R ₂₁ and R ₂₄ each independently represent H or C1-C6 alkyl; R ₂₂ and R ₂₃ each independently represent H or C1-C6 alkyl; or NR ₂₂ R ₂₃ represents

R ₂₅ represents C1-C6 alkyl; A represents halogen and amino; B represents hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, di-C1-C6 alkylamino with or without halogen substitution; C represents halogen, halogenated C1-C6 alkyl. A substituted pyrimidineformyloxime derivative according to any one of claims 1-3, characterized in that: R ₁ and R ₂ independently represent hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, cyano, C1-C4 alkoxycarbonyl, and are unsubstituted or selected from halogen, halogen Phenyl substituted with one or more of C1-C4 alkyl, C1-C4 alkyl, C1-C4 alkoxy, and C2-C4 alkenyl; X represents C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, halogen, C2-C4 alkenyl, C2-C4 alkynyl; Y represents nitro or NR ₃ R ₄ , wherein R ₃ represents H, C1-C4 alkyl, C2-C4 alkenyl, or C2-C4 alkynyl, optionally substituted with 1-2 R ₁₁ , -COR ₁₂ , Nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N = CR ₁₇ R ₁₈ , C1-C4 alkylcarbamoyl, di-C1-C4 alkylcarbamoyl, tri-C1-C4 alkylformyl Silane or di-C1-C4 alkylphosphono; R ₄ represents H, C1-C4 alkyl or -COR ₁₂ optionally substituted with 1-2 R ₁₁ ; or NR ₃ R ₄ represents N = CR ₂₁ NR ₂₂ R ₂₃ , N = CR ₂₄ OR ₂₅ , unsubstituted or 1-2 independently selected from halogen, C1-C4 alkyl, C1-C4 alkoxy, halo C1-C4 alkoxy, C1-C4 alkane Substituted by groups in thio, halo C1-C4 alkylthio, amino, C1-C4 alkylamino, di-C1-C4 alkylamino, C1-C4 alkoxycarbonyl

Where R ₁₁ independently represents halogen, hydroxy, C1-C4 alkoxy, halo C1-C4 alkoxy, C1-C4 alkylthio, halo C1-C4 alkylthio, amino, C1-C4 alkylamino , Di-C1-C4 alkylamino, C1-C4 alkoxycarbonyl, unsubstituted or benzene substituted by 1-3 groups of halogen, C1-C4 alkyl, C1-C4 alkoxy, nitro Base, naphthyl,

R ₁₂ represents H, C1-C8 alkyl, halo C1-C4 alkyl, C1-C4 alkoxy, phenyl, phenoxy or benzyloxy; R ₁₃ represents H, C1-C4 alkyl, halo C1-C4 alkyl, phenyl, benzyl or CHR ₃₁ C (O) OR ₃₂ ; R ₃₁ represents H, C1-C4 alkyl or C1-C4 alkoxy R ₃₂ represents H, C1-C4 alkyl or benzyl; R ₁₄ represents C1-C4 alkyl, halogenated C1-C4 alkyl; R ₁₅ represents H, C1-C4 alkyl, formyl, C1-C4 alkylacyl, halo C1-C4 alkylacyl, C1-C4 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxy Carbonyl; R ₁₆ represents H, C1-C4 alkyl; R ₁₇ represents H, C1-C4 alkyl, unsubstituted or phenyl substituted with 1-3 of halogen, C1-C4 alkyl, C1-C4 alkoxy; R ₁₈ represents H, C1- C4 alkyl; or N = CR ₁₇ R ₁₈ represents

R ₂₁ and R ₂₄ each independently represent H or C1-C4 alkyl; R ₂₂ and R ₂₃ each independently represent H or C1-C4 alkyl; or NR ₂₂ R ₂₃

R ₂₅ represents C1-C4 alkyl; A represents halogen and amino; B represents hydrogen, halogen, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino, di-C1-C4 alkylamino with or without halogen substitution; C represents halogen, halogenated C1-C4 alkyl. The substituted pyrimidineformyloxime derivative according to claim 1, wherein: R ₁ and R ₂ independently represent hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, methylthio, ethylthio, cyano, methoxycarbonyl, Ethoxycarbonyl, and unsubstituted or selected from halogen, CF ₃ , methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, methoxy, and ethoxy Phenyl substituted with one or more groups; X represents chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl; Y represents NH ₂ , NHMe, N (Me) ₂ ,

A represents fluorine, chlorine, and amino; B represents hydrogen, fluorine, chlorine, methoxy, ethoxy, and methylthio with or without fluorine; C stands for fluorine, chlorine, and trifluoromethyl. The substituted pyrimidineformyloxime derivative according to claim 1, wherein the structural formula is any one of the following:

A method for preparing a substituted pyrimidineformyloxime derivative according to any one of claims 1-6, comprising the steps of: using a compound represented by Formula II and a compound represented by Formula III The compound is reacted to prepare a compound represented by the general formula I. The reaction equation is as follows:

Preferably, the reaction is performed in an aprotic solvent under the action of a base and a condensing agent; preferably, the reaction temperature is 0 ° -90 ° C, preferably 25 ° -30 ° C; the solvent is selected from dichloro One or more mixed solvents of methane, dichloroethane, acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene, xylene; The base is selected from one or more of triethylamine, trimethylamine, DIPEA, and DBU; the condensing agent is PyBop, HATU, or HOBt-EDCI. A herbicide composition, comprising at least one of the substituted pyrimidineformyloxime derivatives according to any one of claims 1 to 6 in a herbicidally effective amount, and preferably further comprising a formulation auxiliary. A method for controlling harmful plants, characterized by comprising a herbicidally effective amount of at least one of the substituted pyrimidineformyloxime derivatives according to any one of claims 1 to 6 or the herbicidal agent according to claim 8 The agent composition is used on plants or harmful plant areas. The use of at least one of the substituted pyrimidineformyloxime derivatives according to any one of claims 1 to 6 or the herbicide composition according to claim 8 for controlling harmful plants, preferably, the The substituted pyrimidineformyloxime derivatives are used to control harmful plants in useful crops, which are transgenic crops or crops treated by genome editing technology.