RU2777594C2 - Substituted pyrimidinylformyloxime derivative, its production method, its herbicidal composition, and use - Google Patents

Abstract

FIELD: agriculture.

SUBSTANCE: group of inventions relates to the field of pesticides and includes a compound of the formula I, its production method, an herbicidal composition based on it, a combating method, and the use. In the formula I, R1 and R2 are independently H, halogen, cyano, nitro, C1-C8 alkyl, halogen C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, benzyl, phenoxy, phenylthio, or a group represented by the formula -COR₅, R₅ is such as it is defined in the claims, X is C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, halogen, C2-C8 alkenyl, or C2-C8 alkynyl; Y is nitro or NR₃R₄, where R₃ is H, C1-C8 alkyl, -COR₁₂, nitro, OR₁₃, SO₂R₁₄, NR₁₅R₁₆, N=CR₁₇R₁₈, where C1-C8 alkyl is optionally substituted with one or two groups R₁₁; R₄ is H, C1-C8 alkyl, or -COR₁₂, where C1-C8 alkyl is optionally substituted with one or two groups R₁₁; or NR3R4 is N=CR₂₁NR₂₂R₂₃ or 5- or 6-element saturated or aromatic ring, which is optionally additionally contains an oxygen atom; R_11-18, R_21-23 are such as it is defined in the claims, A is halogen or amino; B is hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, or di C1-C8 alkylamino, where C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, and di C1-C8 alkylamino are independently unsubstituted or substituted with halogen; C is halogen or halogen C1-C8 alkyl.

EFFECT: substituted pyrimidinylformyloxime derivative of the general formula I, having herbicidal activity and selectivity relatively to agricultural crops, such as corn and rice.

13 cl, 4 tbl

Description

The field of technology to which the invention belongs

The invention relates to the field of pesticide technology and, in particular, to the type of substituted derivative of pyrimidinylformyl oxime, the method for its preparation, its herbicidal composition and use.

Prerequisites for the creation of the invention

Weed control is one of the most important links in the process of achieving highly efficient agriculture. Various pyrimidinyl formic acid herbicides are currently available on the market, e.g. also their use as herbicides. However, scientists still need to continue research and develop new herbicides with high efficacy, safety, economy and various modes of action due to issues such as the growing market, weed resistance, pesticide life and economy, as well as the growing concern of people about environmental issues. .

The essence of the invention

The present invention provides a substituted pyrimidinylformyl oxime derivative, a process for preparing the same, a herbicidal composition and use thereof. Said compound has excellent herbicidal activity and higher crop safety, with particularly good selectivity for key crops such as corn and rice.

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

Type of substituted pyrimidinylformyl oxime derivative shown in general formula I:

I

where

R ₁ and R ₂ are independently H, halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, cycloalkyl, alkoxy, acyloxy, alkylthio, unsubstituted or substituted aryl, unsubstituted or substituted benzyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted heteroarylthio, unsubstituted or substituted heteroarylthio, or a group represented by the formula -COR ₅ where R ₅ is alkyl, haloalkyl, alkenyl, cycloalkyl, alkoxy, alkenoxy, cycloalkoxy, alkylthio, alkenylthio, cycloalkylthio, unsubstituted or substituted benzyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aryloxy, unsubstituted or substituted heteroaryloxy, unsubstituted or substituted arylmethoxy, unsubstituted or substituted heteroarylmethoxy, unsubstituted or substituted benzylthio, unsubstituted or substituted arylthio, unsubstituted or substituted heteroarylthio, or ami but which is optionally substituted with alkyl, acyl, acyloxy, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted arylalkyl, or unsubstituted or substituted heteroarylalkyl; or R ₁ and R ₂ are linked to form a 5- or 6-membered saturated or unsaturated ring;

X is alkyl, alkoxy, alkylthio, halogen, alkenyl or alkynyl;

Y is nitro or NR ₃ R ₄ where R ₃ is H, alkyl, alkenyl, alkynyl, -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N=CR ₁₇ R ₁₈ , alkylcarbamoyl , dialkylcarbamoyl, trialkylsilyl or dialkylphosphono, where alkyl, alkenyl and alkynyl are independently optionally substituted with one or two R ₁₁ groups; R ₄ is H, alkyl or -COR ₁₂ where alkyl is optionally substituted with one or two R ₁₁ groups; or NR ₃ R ₄ is N=CR ₂₁ NR ₂₂ R ₂₃ , N=CR ₂₄ OR ₂₅ or a 5- or 6-membered saturated or unsaturated ring which is unsubstituted or substituted with one or two groups selected from halo, alkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, and alkoxycarbonyl, and whether or not it contains an oxygen atom, a sulfur atom, or another nitrogen atom;

where R ₁₁ is independently halogen, hydroxy, alkoxy, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl, unsubstituted or substituted aryl, or unsubstituted or substituted heteroaryl;

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

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

R ₁₄ is alkyl or haloalkyl;

R ₁₅ is H, alkyl, formyl, alkylacyl, haloalkylacyl, alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl; R ₁₆ is H or alkyl;

или

;R ₁₇ is H, alkyl or phenyl, said phenyl being unsubstituted or substituted with 1-3 groups selected from halogen, alkyl and alkoxy; R ₁₈ is H or alkyl; or N=CR ₁₇ R ₁₈ is

or

;

R ₂₁ and R ₂₄ are each independently H or alkyl;

R ₂₂ and R ₂₃ are each independently H or alkyl; or NR ₂₂ R ₂₃ is a 5- or 6-membered saturated or unsaturated ring, containing or not containing an oxygen atom, a sulfur atom, or another nitrogen atom;

R ₂₅ is alkyl;

A is halo or amino;

B represents hydrogen, halogen, alkoxy, alkylthio, alkylamino or dialkylamino, where alkoxy, alkylthio, alkylamino and dialkylamino are independently unsubstituted or substituted with halogen;

C is halo or haloalkyl.

Preferably R ₁ and R ₂ are independently 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, unsubstituted or substituted benzyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aryloxy, unsubstituted or substituted arylthio, unsubstituted or substituted heteroaryloxy, unsubstituted or substituted heteroarylthio, or a group represented by the formula -COR ₅ where R ₅ is C1- C8 alkyl, halo C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C2-C8 alkoxy, C3-C8 cycloalkoxy, C1-C8 alkylthio, C2-C8 alkenylthio, C3-C8 cycloalkylthio, unsubstituted or substituted benzyl, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aryloxy, unsubstituted or substituted heteroaryloxy, unsubstituted or substituted arylmethoxy, unsubstituted or substituted heteroarylmethoxy, unsubstituted or substituted substituted benzylthio, unsubstituted or substituted arylthio, unsubstituted or substituted heteroarylthio, or amino which is optionally substituted by C1-C8 alkyl, C1-C8 acyl, C1-C8 acyloxy, unsubstituted or substituted aryl, unsubstituted or substituted heteroaryl, unsubstituted or substituted aryl C1- C8 alkyl or unsubstituted or substituted heteroaryl C1-C8 alkyl; where said "substituted" refers to substitution with one or more groups selected from halo, cyano, nitro, C1-C8 alkyl, halo, C1-C8 alkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C2-C8 alkenoxy, C1-C8 alkylthio, aryl, aryloxy, benzyl, benzyloxy, C1-C8 acyl, C1-C8 acyloxy, C2-C8 alkenyl and amino which is optionally substituted with C1-C8 alkyl, aryl, aryloxy, C1-C8 acyl, C1-C8 acyloxy or C2 -C8 alkenyl;

X is C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, halo, C2-C8 alkenyl, or C2-C8 alkynyl;

или

при этом

и

независимо являются незамещенными или замещены 1-2 группами, выбранными из галогена, C1-C8 алкила, C1-C8 алкокси, галоген C1-C8 алкокси, C1-C8 алкилтио, галоген C1-C8 алкилтио, амино, C1-C8 алкиламино, диС1-C8 алкиламино и C1-C8 алкоксикарбонила;Y is nitro or NR ₃ R ₄ where R ₃ is H, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N=CR ₁₇ R ₁₈ , C1-C8 alkylcarbamoyl, diC1-C8 alkylcarbamoyl, triC1-C8 alkylsilyl or diC1-C8 alkylphosphono, wherein C1-C8 alkyl, C2-C8 alkenyl and C2-C8 alkynyl are independently optionally substituted with one or two groups R ₁₁ ; R ₄ is H, C1-C8 alkyl, or —COR ₁₂ , with C1-C8 alkyl optionally substituted with one or two R ₁₁ groups; or NR ₃ R ₄ is N=CR ₂₁ NR ₂₂ R ₂₃ , N=CR ₂₄ OR ₂₅ ,

or

wherein

and

are independently unsubstituted or substituted with 1-2 groups selected from halo, C1-C8 alkyl, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino, diC1- C8 alkylamino and C1-C8 alkoxycarbonyl;

или

, при этом фенил, нафтил,

и

независимо являются незамещенными или замещены 1-3 группами, выбранными из галогена, C1-C8 алкила, C1-C8 алкокси и нитро;where R ₁₁ is independently halo, hydroxy, C1-C8 alkoxy, halo C1-C8 alkoxy, C1-C8 alkylthio, halo C1-C8 alkylthio, amino, C1-C8 alkylamino, diC1-C8 alkylamino, C1-C8 alkoxycarbonyl, phenyl , naphthyl,

or

, while phenyl, naphthyl,

and

are independently unsubstituted or substituted with 1-3 groups selected from halo, C1-C8 alkyl, C1-C8 alkoxy, and nitro;

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

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

R ₁₄ is C1-C8 alkyl or halo C1-C8 alkyl;

R ₁₅ is H, C1-C8 alkyl, formyl, C1-C8 alkylacyl, halo C1-C8 alkylacyl, C1-C8 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl; R ₁₆ is H or C1-C8 alkyl;

или

;R ₁₇ is H, C1-C8 alkyl or phenyl, said phenyl being unsubstituted or substituted with 1-3 groups selected from halogen, C1-C8 alkyl and C1-C8 alkoxy; R ₁₈ is H or C1-C8 alkyl; or N=CR ₁₇ R ₁₈ is

or

;

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

или

;R ₂₂ and R ₂₃ are each independently H or C1-C8 alkyl; or NR ₂₂ R ₂₃ is

or

;

R ₂₅ is C1-C8 alkyl;

A is halo or amino;

B is hydrogen, halo, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, or diC1-C8 alkylamino, wherein C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino, and diC1-C8 alkylamino are independently unsubstituted or substituted with halogen;

C is halo or halo C1-C8 alkyl.

In the definition of the general compound formula above, the terms used are defined as follows:

aryl in said R1 and R2 groups preferably includes phenyl, 2,3-dihydroindenyl and naphthyl and the like; said heteroaryl includes 5-10 membered heteroaryl containing 1-3 heteroatoms selected from oxygen, sulfur and nitrogen, such as pyridyl, pyrimidyl, pyrazinyl, furanyl, thienyl, pyrryl, pyrazolyl, thiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazolyl, oxadiazolyl , thiadiazolyl, pyridazinyl, triazinyl, quinolyl, quinoxalinyl, indolyl, benzotriazolyl, benzothienyl, benzofuranyl, isoquinolyl, tetrahydroquinolyl, and the like.

More preferably, R ₁ and R ₂ are independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, cyano, C1-C6 alkoxycarbonyl, or phenyl, said phenyl being unsubstituted or substituted with one or more groups selected from from halogen, halo C1-C6 alkyl, C1-C6 alkyl, C1-C6 alkoxy and C2-C6 alkenyl;

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

или

, при этом

и

независимо являются незамещенными или замещены 1-2 группами, выбранными из галогена, C1-C6 алкила, C1-C6 алкокси, галоген C1-C6 алкокси, C1-C6 алкилтио, галоген C1-C6 алкилтио, амино, C1-C6 алкиламино, диС1-C6 алкиламино и C1-C6 алкоксикарбонила;Y is nitro or NR ₃ R ₄ where R ₃ is H, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N=CR ₁₇ R ₁₈ , C1-C6 alkylcarbamoyl, diC1-C6 alkylcarbamoyl, triC1-C6 alkylsilyl or diC1-C6 alkylphosphono, wherein C1-C6 alkyl, C2-C6 alkenyl and C2-C6 alkynyl are independently optionally substituted with one or two groups R ₁₁ ; R ₄ is H, C1-C6 alkyl, or —COR ₁₂ , with C1-C6 alkyl optionally substituted with one or two R ₁₁ groups; or NR ₃ R ₄ is N=CR ₂₁ NR ₂₂ R ₂₃ , N=CR ₂₄ OR ₂₅ ,

or

, wherein

and

are independently unsubstituted or substituted with 1-2 groups selected from halo, C1-C6 alkyl, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino, diC1- C6 alkylamino and C1-C6 alkoxycarbonyl;

или

, при этом фенил, нафтил,

и

независимо являются незамещенными или замещены 1-3 группами, выбранными из галогена, C1-C6 алкила, C1-C6 алкокси и нитро;where R ₁₁ is independently halo, hydroxy, C1-C6 alkoxy, halo C1-C6 alkoxy, C1-C6 alkylthio, halo C1-C6 alkylthio, amino, C1-C6 alkylamino, diC1-C6 alkylamino, C1-C6 alkoxycarbonyl, phenyl , naphthyl,

or

, while phenyl, naphthyl,

and

are independently unsubstituted or substituted with 1-3 groups selected from halo, C1-C6 alkyl, C1-C6 alkoxy and nitro;

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

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

R ₁₄ is C1-C6 alkyl or halo C1-C6 alkyl;

R ₁₅ is H, C1-C6 alkyl, formyl, C1-C6 alkylacyl, halo C1-C6 alkylacyl, C1-C6 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl; R ₁₆ is H or C1-C6 alkyl;

или

;R ₁₇ is H, C1-C6 alkyl or phenyl, said phenyl being unsubstituted or substituted with 1-3 groups selected from halogen, C1-C6 alkyl and C1-C6 alkoxy; R ₁₈ is H or C1-C6 alkyl; or N=CR ₁₇ R ₁₈ is

or

;

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

или

;R ₂₂ and R ₂₃ are independently H or C1-C6 alkyl; or NR ₂₂ R ₂₃ is

or

;

R ₂₅ is C1-C6 alkyl;

A is halo or amino;

B is hydrogen, halo, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, or diC1-C6 alkylamino, wherein C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino, and diC1-C6 alkylamino are independently unsubstituted or substituted with halogen;

C is halo or halo C1-C6 alkyl.

More preferably, R ₁ and R ₂ are independently hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, cyano, C1-C4 alkoxycarbonyl, or phenyl, said phenyl being unsubstituted or substituted by one or more groups selected from from halogen, halo C1-C4 alkyl, C1-C4 alkyl, C1-C4 alkoxy and C2-C4 alkenyl;

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

или

, при этом

и

независимо являются незамещенными или замещены 1-2 группами, выбранными из галогена, C1-C4 алкила, C1-C4 алкокси, галоген C1-C4 алкокси, C1-C4 алкилтио, галоген C1-C4 алкилтио, амино, C1-C4 алкиламино, диС1-C4 алкиламино и C1-C4 алкоксикарбонила;Y is nitro or NR ₃ R ₄ where R ₃ is H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N=CR ₁₇ R ₁₈ , C1-C4 alkylcarbamoyl, diC1-C4 alkylcarbamoyl, triC1-C4 alkylsilyl or diC1-C4 alkylphosphono, wherein C1-C4 alkyl, C2-C4 alkenyl and C2-C4 alkynyl are independently optionally substituted with 1-2 groups R ₁₁ ; R ₄ is H, C1-C4 alkyl, or —COR ₁₂ , with C1-C4 alkyl optionally substituted with one or two R ₁₁ groups; or NR ₃ R ₄ is N=CR ₂₁ NR ₂₂ R ₂₃ , N=CR ₂₄ OR ₂₅ ,

or

, wherein

and

are independently unsubstituted or substituted with 1-2 groups selected from halo, C1-C4 alkyl, C1-C4 alkoxy, halo C1-C4 alkoxy, C1-C4 alkylthio, halo C1-C4 alkylthio, amino, C1-C4 alkylamino, diC1- C4 alkylamino and C1-C4 alkoxycarbonyl;

или

, при этом фенил, нафтил,

и

независимо являются незамещенными или замещены 1-3 группами, выбранными из галогена, C1-C4 алкила, C1-C4 алкокси и нитро;where R ₁₁ is independently halo, hydroxy, C1-C4 alkoxy, halo C1-C4 alkoxy, C1-C4 alkylthio, halo C1-C4 alkylthio, amino, C1-C4 alkylamino, diC1-C4 alkylamino, C1-C4 alkoxycarbonyl, phenyl , naphthyl,

or

, while phenyl, naphthyl,

and

are independently unsubstituted or substituted with 1-3 groups selected from halo, C1-C4 alkyl, C1-C4 alkoxy and nitro;

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

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

R ₁₄ is C1-C4 alkyl or halo C1-C4 alkyl;

R ₁₅ is H, C1-C4 alkyl, formyl, C1-C4 alkyl acyl, halo C1-C4 alkyl acyl, C1-C4 alkoxycarbonyl, phenylcarbonyl, phenoxycarbonyl or benzyloxycarbonyl; R ₁₆ is H or C1-C4 alkyl;

или

;R ₁₇ is H, C1-C4 alkyl or phenyl, said phenyl being unsubstituted or substituted with 1-3 groups selected from halogen, C1-C4 alkyl and C1-C4 alkoxy; R ₁₈ is H or C1-C4 alkyl; or N=CR ₁₇ R ₁₈ is

or

;

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

или

;R ₂₂ and R ₂₃ are independently H or C1-C4 alkyl; or NR ₂₂ R ₂₃ is

or

;

R ₂₅ is C1-C4 alkyl;

A is halo or amino;

B is hydrogen, halogen, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino, or diC1-C4 alkylamino, wherein C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino, and diC1-C4 alkylamino are independently unsubstituted or substituted with halogen;

C is halo or halo C1-C4 alkyl.

Even more preferably R ₁ and R ₂ are independently hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, methylthio, ethylthio, cyano, methoxycarbonyl, ethoxycarbonyl or phenyl, said phenyl being unsubstituted or substituted with one or more groups selected from halogen, CF ₃ , methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, methoxy and ethoxy;

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

или

;Y is NH ₂ , NHMe, N(Me) ₂ ,

or

;

A is fluorine, chlorine or amino;

B represents hydrogen, fluorine, chlorine, methoxy, ethoxy or methylthio, with methoxy, ethoxy and methylthio independently containing or not containing fluorine;

C represents fluorine, chlorine or trifluoromethyl.

A process for preparing a substituted pyrimidinylformyl oxime derivative, which includes the following steps:

a compound of general formula II and a compound of general formula III are reacted to obtain a compound of general formula I, the chemical reaction scheme is as follows:

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

The temperature of this reaction is in the range from 0°C to 90°C, more preferably from 25°C to 30°C.

The solvent is a single solvent or multiple mixed solvents selected from dichloromethane, dichloroethane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, toluene, and xylene.

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

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

A herbicidal composition comprising a herbicidally effective amount of at least one substituted pyrimidinylformyl oxime derivative.

Herbicidal composition further comprising a formulation aid.

A method for controlling a pest, comprising applying a herbicidally effective amount of at least one substituted pyrimidinylformyl oxime derivative or herbicidal composition to the pest or to an area with the pest.

Use of at least one substituted pyrimidinylformyl oxime derivative or herbicidal composition to control a pest.

Preferably, the substituted pyrimidinylformyl oxime derivative is used to control a pest in a useful crop.

More preferably, the useful culture is a genetically modified or genome-edited culture.

The compounds of formula I according to the invention have remarkable herbicidal activity against a wide range of economically important monocot and dicot pests. The active compounds are also effective against perennial weeds that form roots from rhizomes, rhizomes or other perennial organs and are difficult to control. In this context, as a rule, it does not matter whether pre-sowing, pre-emergence or post-emergence application of the substance is carried out. In particular, it is possible to give examples of some representatives of monocots and dicots weeds that can be controlled with the compounds according to the invention, without being limited to specific species. Examples of weed species that are effectively affected by the active compounds are, among the monocotyledonous, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria, as well as Cyperus species from annuals, and from among the perennial species of Agropyron, Cynodon, Imperata and Sorghum , as well as perennial species of Cyperus.

In the case of dicotyledonous weed species, the spectrum of action extends to species such as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amarantus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon from the annuals, and Convolvulus, Cirsium, Rumex and Artemisia for perennial weeds. The active compounds according to the invention also provide excellent control of harmful plants that appear under specific rice growing conditions, such as, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus. If the compounds according to the invention are applied to the soil surface prior to germination, then either the emergence of weeds is completely prevented, or the weeds grow until they reach the cotyledon phase, but then their growth stops, and eventually stops after three to four weeks, they are completely are dying. In particular, the compounds according to the invention show excellent activity against Apera spica venti, Chenopodium album, Lamium purpureum, Polygonum convulvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor and against Amarantus, Galium and Kochia species.

Although the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, cultivated plants of economically important crops such as, for example, wheat, barley, rye, rice, corn, sugar beet, cotton and soybeans are not damaged at all, either only to a small extent. In particular, they have excellent compatibility in cereals such as wheat, barley and corn, in particular wheat. Therefore, the compounds of the present invention are extremely suitable for selectively controlling the growth of undesirable plants in agricultural or ornamental plantings.

Due to their herbicidal properties, these active compounds can also be used to control harmful plants in cultivated crops of genetically engineered plants that are known or yet to be developed. Transgenic plants typically have particularly beneficial properties, such as resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases, or resistance to plant disease causing organisms such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific properties relate, for example, to quantity, quality, storage stability, composition, and specific ingredients of the harvested product. Thus, transgenic plants are known having increased starch content or modified starch quality, or those having a different fatty acid composition in the harvested product.

The use of the compounds of formula I according to the invention or their salts in economically important transgenic cultivated crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn, or also in such crops, like sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetable species is preferred. The compounds of formula I can preferably be used as herbicides in cultivated crops of useful plants that are resistant or have been genetically engineered to be resistant to the phytotoxic effects of herbicides.

Traditional ways to obtain new plants that have modified properties compared to known plants include, for example, traditional methods of propagation and creation of mutants. Alternatively, new plants having modified properties can be obtained by genetic engineering methods (see, for example, EP-A 0 221 044, EP-A 0 131 624). For example, some cases are described:

- genetically engineered changes in cultivated plants to modify the starch synthesized in plants (eg WO 92/11376, WO 92/14827, WO 91/19806);

- transgenic crop plants which are resistant to certain herbicides, for example glufosinate (EP-A 0 242 236, EP-A 0 242 246), glyphosate type (WO 92/00377) or sulfonylurea type (EP-A 0 257 993, US Pat. No. 5013659);

- transgenic crop plants, such as cotton, having the ability to produce Bacillus thuringiensis toxins (Bt toxins), which confer resistance to certain plant pests (EP-A 0 142 924, EP-A 0193259);

- transgenic crop plants having a modified fatty acid composition (WO 91/13972).

In principle, numerous molecular biological methods are known that make it possible to obtain new transgenic plants with modified properties; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim, 2nd edition 1996, or Christou, "Trends in Plant Science" 1 (1996) 423-431). To carry out such genetic engineering manipulations, it is possible to introduce nucleic acid molecules into plasmids that allow mutagenesis or changes in sequence by recombination of DNA sequences. Using the above standard procedures, it is possible, for example, to exchange bases, remove partial sequences, or add natural or synthetic sequences. To link DNA fragments to each other, adapters or linkers can be attached to the fragments.

Plant cells having reduced activity of a gene product can be obtained, for example, by expressing at least one suitable antisense RNA, sense RNA to achieve a co-suppression effect, or expression of at least one suitably designed ribozyme that specifically cleaves transcripts of said gene product. .

For this purpose, both DNA molecules that contain the entire coding sequence of the gene product, including any flanking sequences that may be present, and DNA molecules that contain only parts of the coding sequence, it is necessary that these parts are of sufficient length so that induce an antisense effect in cells. It is also possible to use DNA sequences that have a high degree of homology with the coding sequences of the gene product, but which are not completely identical.

When the nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any desired compartment of plant cells. However, to achieve localization in a particular compartment, one can, for example, link the coding region to DNA sequences that allow localization in a particular compartment. Such 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 regenerated into whole plants using known methods. The transgenic plants can in principle be plants of any desired plant species, ie both monocots and dicots. It is thus possible to obtain transgenic plants which have modified properties by overexpressing, suppressing or inhibiting homologous (=natural) genes or gene sequences or by expressing heterologous (=foreign) genes or gene sequences.

When the active compounds according to the invention are used in transgenic crops, in addition to the effects against harmful plants that can be observed in other crops, there are often effects that are specific to the use in the corresponding transgenic crop, for example, an altered or specifically extended range of weeds with which can be controlled, modified application rates that can be used for application, preferably good compatibility with herbicides to which the transgenic crops are resistant, and an effect on the growth and yield of the transgenic crops. Thus, the invention also provides for the use of the compounds according to the invention as herbicides for the control of harmful plants in transgenic crop plants.

In addition, the substances according to the invention have excellent growth regulating properties in crops. They are involved in plant metabolism in a regulatory manner and this can be used to target plant components and to facilitate harvesting, for example by causing desiccation and stunting. In addition, they are also suitable for the general regulation and inhibition of unwanted vegetative growth without destroying the plants. Inhibition of vegetative growth plays an important role in many monocots and dicots, as lodging can be reduced or completely prevented in this way.

The compounds according to the invention can be used in the form of conventional compositions in the form of wettable powders, emulsifiable concentrates, spray solutions, dusts or granules. Thus, the invention also provides herbicidal compositions comprising compounds of formula I. Compounds of formula I can be formulated into various compositions depending on the prevailing biological and/or chemical-physical parameters. Examples of suitable formulation options include: wettable powders (WP), water soluble powders (SP), water soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions , suspension concentrates (SC), oil-based or water-based dispersions, oil-miscible solutions, dusts (DP), capsule suspensions (CS), seed disinfection compositions, granules for spreading and soil application, granules (GR) in the form of microgranules, granules spray, coating and adsorption granules, water dispersible granules (WG), water soluble granules (SG), ULV formulations, microcapsules and waxes. These individual composition types are known in principle and are described, for example, in Winnacker-Kuhler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th. Edition 1986; Wade van Valkenburg, "Pestivide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inerts, surfactants, solvents and other additives are also known and described in, for example, Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, Solvents Guide; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, "Grenzflchenaktive thylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

Wettable powders are preparations which are uniformly dispersed in water and which contain, in addition to the active compound and a diluent or inert agent, surfactants of the ionic and/or non-ionic type (wetting agents, dispersing agents), e.g. polyethoxylated alkylphenols , polyethoxylated fatty alcohols, polyethoxylated fatty amines, polyglycol fatty alcohol ether sulfates, alkane sulfonates, alkylbenzenesulfonates, sodium lignin sulfonate, sodium 2,2'-dinaphtylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or also sodium oleoylmethyltaurinate. To obtain wettable powders, the herbicidally active compounds are finely ground, for example in conventional devices such as hammer mills, fan mills and jet mills, and mixed simultaneously or sequentially with formulation aids.

Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent such as butanol, cyclohexanone, dimethylformamide, xylene, or relatively high boiling aromatic compounds or hydrocarbons, or solvent mixtures, with the addition of one or more ionic and/or non-ionic type surfactants (emulsifiers) . Examples of emulsifiers that can be used include calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate or non-ionic emulsifiers such as polyglycol fatty acid esters, alkylaryl polyglycol ethers, polyglycol fatty alcohol esters, propylene oxide-ethylene oxide condensates, alkyl polyesters, sorbitan esters. , for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active compound with fine solids, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates may be water or oil based. They can be obtained, for example, by wet grinding using conventional commercially available bead mills with or without the addition of surfactants, as already mentioned above, for example in the case of other types of compositions.

Emulsions, such as oil-in-water (EW) emulsions, can be prepared, for example, using stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if desired, surfactants, as already mentioned above, for example in the case of other types of compositions.

Granules can be obtained either by spraying the active compound onto an adsorbable granular inert material, or by applying concentrates of the active substance to the surface of carriers such as sand, kaolinites or granular inert material using adhesive binders, for example polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitable active compounds can also be granulated in the usual way to obtain fertilizer granules, if desired, as a mixture with fertilizers. Water-dispersible granules are generally produced by conventional methods such as spray drying, fluid bed granulation, disk granulation, mixing using high speed mixers, and extrusion without solid inert material.

For the production of granules using a disk granulator, a fluidized bed, an extruder and a spray, see, for example, the methods described in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff.; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. A more detailed description of the preparation of plant protection product compositions can be found, for example, in G.C. Klingman, "Weed Control as a Science", John Wiley and Sons Inc., New York, 1961, pages 81-96, and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

Agrochemical compositions typically contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of the active compound of formula I. In wettable powders, the concentration of the active compound is, for example, from about 10 to 99% mass., the rest of the amount up to 100% of the mass. constitute the traditional components of the composition. In emulsifiable concentrates, the active compound concentration may be from about 1 to 90%, preferably from 5 to 80%, by weight. Compositions in the form of dusts contain from 1 to 30% of the mass. active compound, preferably and most typically from 5 to 20% of the mass. active compound, while spray solutions contain from about 0.05 to 80%, preferably from 2 to 50 wt. active connection. In the case of water-dispersible granules, the content of the active compound depends in part on whether the active compound is in liquid or solid form and also on the granulation auxiliaries, fillers, etc. used. In water-dispersible granules, the active compound content is, for example, from 1 to 95% by weight, preferably from 10 to 80% by weight.

In addition, active compound compositions may include tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes, solvents, fillers, carriers, colorants, defoamers, evaporation inhibitors, and pH and viscosity adjusters that are conventionally used in every case.

These compositions can also be combined with other pesticidally active substances, for example insecticides, acaricides, herbicides and fungicides, as well as safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or tank mix.

Suitable active compounds which can be combined with active compounds according to the invention in mixed formulations or tank mix are, for example, known active compounds as described, for example, in the World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, 2010.9 and in the literature cited in this document. For example, the following active compounds can be listed as herbicides that can be combined with compounds of formula I (Note: compounds are presented either under the "common name" according to the International Organization for Standardization (ISO), or under the chemical name, if necessary, together with conventional code number): acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propachlor, ethachlor, napropamide, R-levo napropamide, propanil, mefenacet, diphenamide, diflufenican, etaprochlor, beflubutaide, bromobutide, dimethenamid, dimethenamid- P, etobenzanide, fluphenacet, tenylchlor, metazachlor, isoxaben, flamprop-M-methyl, flamprop-M-propyl, allidochlor, petoxamide, chloranocryl, cyprazine, mefluidine, monalid, delachlor, prinachlor, terbuchlor, xylachlor, dimethachlor, cisanilide, trimexachlor, clomeprop, propizamide, pentanochlor, carbetamide, benzoylprop-ethyl, ciprazole, butenachlor, tebutam, benzipram, mogrton, dichlofluanid, naproanilide, diethatyl-ethyl, naptalam, flufenacet, benzadox, chlorthiamide, chlorphthalimide, isocarbamide, picolinafen, atrazine, simazine, promethrin, cyanathrine, symetrin, ametrin, propazine, dipropetrin, SSH-108, terbutrin, terbutylazine, triaziflam, ciprazine, proglinazine, trietazine, prometone, simetone, aziprothrin, desmetrin, dimethamethrin, procyazine, mesoprazine, sebutylazine, secbumeton, terbumeton, metoprotrin, cyanathrine, irazine, chlorazine, atratone, pendimethalin, eglinazine, cyanuric acid, indaziflam, chlorsulfuron, metsulfuron-methylon, bensulfuron methyl, chlorimuron-ethyl, triben methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, mesosulfuron, sodium iodosulfuron-methyl, foramsulfuron, cinosulfuron, triasulfuron, sulfometuron methyl, nicosulfuron, etametsulfuron-methyl, amidosulfuron, ethoxysulfuron, cyclosulfamuron, rimsulfuron, azimsulfuron, flazasulfuron, monosulfuron, mono, flucarbazone sodium, flupyrsulfuron methyl, halosulfuron methyl, oxasulfuron, imazosulfuron, primisulfuron, propo xycarbazone, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron, sodium metsulfuron methyl, flucetosulfuron, HNPC-C, orthosulfamuron, propirisulfuron, metazosulfuron, acifluorfen, fomesafen, lactofen, fluoroglycofen, oxyfluorfen, chlornitrofen, afenoxyl-clone, ethosulfuron , Chlomethoxifen, Fluorodiphene, Fluoronitrophen, Furyloxifene, Nitrofen, TOPE, DMNP, PPG1013, AKH-7088, Halosafen, Chlortoluron, Isoproturon, Linuron, Diuron, Dimron, Fluometuron, Benzthiazuron, Metabenzthiazuron, Cumiluron, Ethidimuron, Isouron, Bromomuron, Buturon, Chlorine , methyldymron, fenobenzuron, SK-85, metobromuron, methoxuron, afesin, monuron, siduron, fenuron, fluothiuron, neburon, chloroxuron, noruron, isonoruron, 3-cyclooctyl-1, thiazfluron, tebuthiuron, difenoxuron, parafluron, methylamine tribunil, carbutylate, trimeturon, dimefuron, monisouron, anisuron, methiuron, chloreturon, tetrafluron, phenmedipham, phenmedipham-ethyl, desmedifam, asulam, terbucarb, barban, profam, chlorpropham, roumate, swep, chlorbufam, carboxazole, chlorprocarb, fenasulam, BCPC, CPPC, carbasulam, butylate, bentiocarb, vernolate, molinate, triallate, dimepiperate, esprocarb, pyributicarb, cycloate, avadex, EPTC, etiolate, orbencarb, pebulate, prosulfocarb, thiocarbazyl, CDEC, dimexano, isorolinate, methiobencarb, 2,4-D butyl ether, MCPA-Na, 2,4-D isooctyl ether, MCPA isooctyl ether, 2,4-D sodium salt, 2,4-D salt dimethylamine, MCPA-thioethyl, MCPA, 2,4-D propionic acid, salt of higher 2,4-D propionic acid, 2,4-D butyric acid, MCPA propionic acid, MCPA salt of propionic acid, MCPA butyric acid, 2.4 ,5-D, 2,4,5-D propionic acid, 2,4,5-D butyric acid, MCPA amine salt, dicamba, erbon, chlorofenac, saison, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluazifop -butyl, fluazifop-p-butyl, haloxifop-methyl, haloxifop-P, quizalofop-ethyl, quizalofop-p-ethyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, propyzafop, cyhalofop-butyl, methamifop, clodanifop-propargyl , fentiaprop-ethyl, chlorazifop-propynyl, poppenate-methyl, triphopsime, isoxapyrifop, paraquat, diquat, oryzalin, ethalfluralin, isopropalin, nitralin, profluralin, prodynamine, benfluralin, fluchloralin, dinitramine, dipropaline, chloronidine, metalpropalin, dipoprop, glyphosate, anilophos , ammonium glufosinate, amiprofos-methyl, sulfosate, piperophos, bialaphos-sodium, bensulide, butamiphos, focarb, 2,4-DEP, H-9201, zitron, imazapyr, imazethapir, imazakhin, imazamox, imazamox ammonium salt, imazapic, imazamethabenz- methyl, fluroxypyr, flugoxypyr isooctyl ether, clopyralid, picloram, triclopyr, dithiopyr, haloxydin, 3,5,6-trichloro-2-pyridinol, thiazopyr, fluridone, aminopyralid, diflufenzopyr, triclopyr-butotyr, Cliodinate, sethoxydim, cletodim, cycloxidim, alloxydim, clefoxidim, butroxydim, tralkoxydim, tepraloxydim, butidazole, metribuzin, hexazinon, metamitron, etiosin, ametridione, amibusin, bromoxynil, bromoxynil octanoate, ioxynyl octanoate, ioxynil, dichlobenil, diphenatrile, pyraclonil, chlorine oxynil, iodobonil, flumetsulam, florasulam, penoxsulam, methosulam, cloransulam-methyl, diclosulam, pyroxsulam, benfuresate, bispyribac-sodium, pyribenzoxime, pyrifthalide, pyriminobac-methyl, pyrithiobac-sodium, benzobicilone, mesotrione, sulcotrione, tembotrione, bicyclopyrone, tefuryltrione, ketopyradox, isoxaflutol, clomazone, fenoxasulfone, methiozolin, fluazolate, pyraflufen-ethyl, pyrazolinate, difenzoquat, pyrazoxyfen, benzofenap, nipyraclofen, pyrasulfotol, topramesone, pyroxasulfone, cafestrol, fluroxam, aminotriazole, amicarbazone, azaphenidine, carbentrazone-ethyl, sulfentrazone-ethyl, benzfendizone, butafenacil, bromacyl, isocyl, lenacil, terbacil, flupropacil, cinidone-ethyl, flumiclorac-pentyl, flumioxazine, propizamide, MK-129, flumezin, pentachlorophenol, dinoseb, dinoterb, dinoterb acetate, dinosam, DNOC, chlornitrofen, medinoterb acetate, dinophenate, oxadiargyl, oxadiazon, pentoxazon, flufenacet, fluthiacet-methyl, fentrazamide, flufenpyr-ethyl, pyrazon, bromopyrazon, metflurazon, cusa kira, dimidazone, oxapirazone, norflurazone, pyridafol, quinclorac, hinmerac, bentazone, pyridate, oxaziclomefone, benazoline, clomazone, cinmethylin, ZJ0702, pyribambenz-propyl, indanophane, sodium chlorate, dalapon, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, cyperpropanate , bromophenoxime, epronase, methazol, flurtamone, benfuresate, etofumesate, thioclorim, chlorothal, fluorochloridone, tavron, acrolein, bentranil, tridiphan, chlorophenpropmethyl, thidiarizonaimine, phenizopham, buzoxynone, methoxyphenone, saflufenacil, claciphos, chloropon, methoxyphenone, saflufenacil, clacifos, chloropon, chloropon, alorak, diethniampmiquatam , ipfencarbazone, thiencarbazone-methyl, pyrimisulfae, chlorflurazol, tripropindan, sulglycapine, prosulfalin, cambendichlor, aminocyclopyrachlor, rodetanil, benoxacor, fenclorim, flurazol, fenchlorazole-ethyl, cloquintocet-mexil, oxabethrinil, MG/91, cyometrinil, DKA-24 -diethyl, furilazole, fluxofenim, isoxadifen-ethyl, dichlormide, halauxifen-methyl, DOW florpyrauxifen, 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.

For use, compositions which are present in commercially available form are diluted if necessary in the usual manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Products in the form of dusts, granules for applying or spraying on the ground, and solutions for spraying are usually not diluted with other inert substances before use. The required rate of application of the compounds of formula I varies depending on external conditions such as temperature, humidity, the nature of the herbicide used, and the like. It can vary within wide limits, for example from 0.001 to 1.0 kg/ha or more of active substance, but is preferably from 0.005 to 750 g/ha, in particular from 0.005 to 250 g/ha.

Specific way to carry out the invention

The embodiments described below are used to illustrate the present invention in detail and should not be construed as limiting the present invention. The scope of the invention is explained by the claims.

In view of the economy, diversity and biological activity of the compound, several compounds were preferably synthesized, some of which are shown in the following Table 1. The structure and data for certain compounds are shown in Table 1-2. The compounds in Table 1 are provided to further explain the present invention and not to limit it in any way. The present invention should not be construed by those skilled in the art as being limited to the following compounds.

Table 1
Connection structure

table 2
¹ H NMR data for compounds No. ¹ NMR one ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.43 (m, 5H), 7.31-7.22 (m, 2H), 3.91 (s, 3H), 3.16 (s, 3H), 3.00 (s, 2H). 2 ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.43 (m, 5H), 7.28 (d, J=7.4 Hz, 1H), 7.21 (dd, J=7 .4, 5.6 Hz, 1H), 5.80 (s, 2H), 3.93 (s, 3H), 3.81 (s, 3H), 3.19 (s, 3H). 3 ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.43 (m, 5H), 7.31-7.22 (m, 2H), 5.80 (s, 2H), 3.91 (s, 3H), 3.17 (s, 3H). four ¹ H NMR (500 MHz, Chloroform-d) δ 7.48 (tq, J=7.1, 4.2, 3.6 Hz, 1H), 7.41-7.32 (m, 4H), 7.30-7.19 (m, 1H), 5.80 (s, 2H), 3.89 (s, 3H). 5 ¹ H NMR (500 MHz, Chloroform-d) δ 7.61 (q, J=7.7 Hz, 4H), 7.46 (tt, J=7.4, 2.0 Hz, 1H), 7 .30-7.22(m, 3H), 7.25-7.15(m, 3H), 5.80(s, 2H), 3.88(s, 3H). 6 ¹ H NMR (500 MHz, Chloroform-d) δ 7.71 (s, 1H), 7.53-7.47 (m, 3H), 7.42 (dh, J=5.4, 2.0, 1.6 Hz, 2H), 7.34-7.24 (m, 2H), 3.91 (s, 3H), 3.02 (s, 3H), 2.16 (s, 3H). 7 ¹ H NMR (500 MHz, Chloroform-d) δ 7.55-7.49 (m, 2H), 7.46 (dt, J=9.7, 1.6 Hz, 1H), 7.35-7 .24 (m, 6H), 7.25 (dd, J=7.5, 5.5 Hz, 1H), 5.80 (s, 2H), 3.91 (s, 3H). eight ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.42 (m, 5H), 7.32-7.25 (m, 2H), 5.80 (s, 2H), 3.92 (s, 3H), 3.14 (s, 3H), 2.39 (s, 3H). 9 ¹ H NMR (500 MHz, DMSO-d 6 ) 7.62 (td, J=8.3, 7.6, 1.8 Hz, 1H), 7.41 (dd, J=8.6, 1, 5 Hz, 1H), 3.89 (s, 3H) 2.44-2.30 (m, 2H), 2.0 (s, 3H), 1.05 (sq., J=7.8 Hz, 3H). ten ¹ H NMR (500 MHz, Chloroform-d) δ 7.58-7.51 (m, 2H), 7.55-7.46 (m, 3H), 7.30-7.20 (m, 2H) , 6.05 (dt, J=14.1, 12.3, 6.2 Hz, 1H), 5.12 (dt, J=14.3, 1.3 Hz, 2H), 3.95 (s , 3H), 3.39 (dt, J=6.3, 1.1 Hz, 2H), 2.66 (s, 2H). eleven ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.42 (m, 5H), 7.42 (d, J=7.5 Hz, 1H), 7.27 (d, J=7 .3 Hz, 1H), 5.80 (s, 2H), 3.85 (s, 3H), 3.04 (s, 3H). 12 ¹ H NMR (500 MHz, Chloroform-d) δ 7.68 (dd, J=8.7, 7.4 Hz, 1H), 7.24-7.17 (m, 1H), 5.80 (s , 2H), 3.99 (s, 3H), 2.12 (s, 3H), 2.04 (s, 3H). 13 ¹ H NMR (500 MHz, Chloroform-d) δ 7.39 (dd, J=7.5, 5.7 Hz, 1H), 7.28 (d, J=7.5 Hz, 1H), 5, 80 (s, 2H), 3.87 (s, 3H), 3.64 (sq., J=8.0 Hz, 2H), 2.11 (t, J=8.0 Hz, 2H), 1 .60-1.50 (m, 2H), 1.40 (dtd, J=13.4, 8.0, 5.4 Hz, 2H), 1.28 (t, J=8.0 Hz, 3H ), 0.95 (t, J=8.0 Hz, 3H). fourteen ¹ H NMR (500 MHz, Chloroform-d) δ 7.48 (d, J=7.5 Hz, 1H), 7.43 (d, J=7.5 Hz, 1H), 5.80 (s, 2H), 3.82 (s, 3H). fifteen ¹ H NMR (500 MHz, Chloroform-d) δ 7.33-7.23 (m, 2H), 5.80 (s, 2H), 4.46 (q, J=9.1 Hz, 2H) , 2.11 (t, J=5.4 Hz, 2H), 1.54 (dtd, J=10.7, 8.0, 5.4 Hz, 2H), 0.91 (t, J=8 .0 Hz, 3H). 16 ¹ H NMR (500 MHz, Chloroform-d) δ 7.40 (dd, J=7.5, 5.7 Hz, 1H), 7.30 (d, J=7.5 Hz, 1H), 5, 80 (s, 2H), 3.86 (s, 3H). 17 ¹ H NMR (500 MHz, Chloroform-d) δ 7.38 (d, J=7.5 Hz, 1H), 7.29 (d, J=7.5 Hz, 1H), 5.80 (s, 2H), 3.86 (s, 3H), 2.63 (s, 6H). eighteen ¹ H NMR (500 MHz, Chloroform-d) δ 7.49 (d, J=7.5 Hz, 1H), 7.08 (d, J=7.5 Hz, 1H), 5.80 (s, 2H), 4.51 (s, 2H), 3.79 (s, 3H), 3.60 (t, J=7.9 Hz, 2H), 2.51 (s, 3H), 2.41 ( t, J=7.9 Hz, 2H). 19 ¹ H NMR (500 MHz, Chloroform-d) δ 7.46 (tt, J=6.8, 2.6 Hz, 1H), 7.43-7.35 (m, 3H), 7.32-7 .21 (m, 6H), 6.92 (d, J=7.5 Hz, 1H), 4.51 (s, 2H), 2.72 (s, 2H), 2.33 (s, 3H) . twenty ¹ H NMR (500 MHz, Chloroform-d) δ 7.54-7.47 (m, 3H), 7.45 (dtt, J=5.4, 3.5, 1.5 Hz, 2H), 7 .33 (d, J=7.5 Hz, 1H), 6.98 (d, J=7.5 Hz, 1H), 5.80 (s, 2H), 4.51 (s, 2H), 3 .94 (s, 3H), 3.80 (s, 3H), 2.97 (s, 3H). 21 ¹ H NMR (500 MHz, Chloroform-d) δ 7.50 (d, J=7.5 Hz, 1H), 7.51-7.39 (m, 3H), 7.35-7.21 (m , 6H), 7.20-7.11 (m, 1H), 5.80 (s, 2H). 22 ¹ H NMR (500 MHz, Chloroform-d) δ 7.71 (s, 1H), 7.58 (dt, J=7.5, 5.7 Hz, 1H), 6.91 (dd, J=9 .0, 7.5 Hz, 1H), 6.46 (t, J=7.1 Hz, 1H), 2.22-2.12 (m, 2H), 2.16 (s, 3H), 0 .96 (t, J=8.0 Hz, 3H). 23 ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.43 (m, 4H), 7.41 (d, J=7.5 Hz, 1H), 7.34 (dd, J=7 .5, 5.7 Hz, 1H), 5.80 (s, 2H), 2.46 (s, 3H). 24 ¹ H NMR (500 MHz, Chloroform-d) δ 7.52-7.41 (m, 2H), 7.11 (td, J=7.5, 2.0 Hz, 1H), 7.00 (dd , J=7.4, 5.8 Hz, 1H), 6.98-6.90 (m, 2H), 3.91 (s, 3H), 3.81 (s, 3H), 3.11 ( s, 3H), 2.96 (s, 6H), 1.50 (s, 1H). 25 ¹ H NMR (500 MHz, Chloroform-d) δ 7.58 (dt, J=7.1, 2.1 Hz, 1H), 7.32-7.22 (m, 2H), 7.20 (d , J=7.5 Hz, 1H), 7.12 (dd, J=7.5, 5.7 Hz, 1H), 7.05 (tt, J=2.1, 1.1 Hz, 1H) , 5.80 (s, 2H), 5.44 (s, 2H), 2.92 (s, 3H), 2.47 (s, 3H), 2.33-2.23 (m, 2H), 1.27 (t, J=8.0 Hz, 3H). 26 ¹ H NMR (500 MHz, Chloroform-d) δ 7.86-7.80 (m, 2H), 7.64-7.58 (m, 2H), 7.36 (d, J=7.5 Hz , 1H), 7.25 (dd, J=7.5, 5.7 Hz, 1H), 5.80 (s, 2H), 2.77 (s, 3H), 2.51 (s, 3H) , 2.06 (s, 1H). 27 ¹ H NMR (500 MHz, Chloroform-d) δ 8.31-8.24 (m, 2H), 7.62-7.55 (m, 2H), 7.30 (d, J=7.5 Hz , 1H), 7.21 (dd, J=7.5, 5.7 Hz, 1H), 5.80 (s, 2H), 3.12 (s, 3H). 28 ¹ H NMR (500 MHz, Chloroform-d) δ 7.48 (s, 1H), 7.40-7.31 (m, 3H), 7.34-7.26 (m, 2H), 7.03 (dd, J=7.5, 5.9 Hz, 1H), 5.80 (s, 2H), 3.97 (s, 3H), 3.62 (sq., J=8.0 Hz, 2H ), 2.48 (s, 3H), 2.10 (s, 3H), 1.24 (t, J=8.0 Hz, 3H). 29 ¹ H NMR (500 MHz, Chloroform-d) δ 7.71 (s, 1H), 7.40 (s, 5H), 7.34 (d, J=7.5 Hz, 1H), 3.85 ( s, 3H), 2.46 (d, J=14.8 Hz, 6H), 2.34 (s, 3H), 2.16 (s, 3H). thirty ¹ H NMR (500 MHz, Chloroform-d) δ 7.36-7.27 (m, 2H), 7.21-7.15 (m, 2H), 6.78-6.72 (m, 2H) , 5.80 (s, 2H), 3.74 (s, 3H), 3.02 (s, 6H), 2.48 (s, 3H). 31 ¹ H NMR (500 MHz, Chloroform-d) δ 7.71 (s, 1H), 7.30 (d, J=7.5 Hz, 1H), 7.27-7.16 (m, 3H), 7.19-7.13(m, 2H), 6.93-6.86(m, 2H), 6.82-6.74(m, 1H), 6.78-6.68(m, 2H ), 4.77 (s, 1H), 3.93 (s, 3Hs), 2.15 (d, J=6.4 Hz, 6H). 32 ¹ H NMR (500 MHz, Chloroform-d) δ 7.40-7.35 (m, 2H), 7.33-7.20 (m, 8H), 5.80 (s, 2H), 3.92 (s, 3H), 2.42 (s, 3H), 1.91-1.82 (m, 1H), 1.18-1.10 (m, 2H), 0.91-0.83 (m , 2H). 33 ¹ H NMR (500 MHz, Chloroform-d) δ 7.32-7.20 (m, 4H), 7.04-6.99 (m, 2H), 6.37-6.31 (m, 1H) , 5.80 (s, 2H), 4.97 (dsq, J=11.0, 6.4 Hz, 1H), 4.23 (sq, J=8.0 Hz, 2H), 3, 93 (s, 3H), 2.59 (s, 3H), 1.70 (dd, J=6.4, 1.1 Hz, 3H), 1.31 (t, J=8.0 Hz, 3H ). 34 ¹ H NMR (500 MHz, Chloroform-d) δ 7.52-7.45 (m, 1H), 7.38 (dt, J=6.1, 2.0 Hz, 3H), 7.32 (tdd , J=10.2, 4.5, 2.7 Hz, 5H), 7.28-7.20 (m, 1H), 7.07 (td, J=7.5, 2.0 Hz, 1H ), 6.73 (td, J=7.4, 1.9 Hz, 1H), 6.62 (dd, J=7.4, 2.0 Hz, 1H), 6.41-6.32 ( m, 2H), 5.17 (s, 2H), 4.93 (s, 1H), 4.93 (d, J=2.1 Hz, 1H), 3.94 (s, 3H). 35 ¹ H NMR (500 MHz, Chloroform-d) δ 7.36-7.29 (m, 4H), 7.32-7.19 (m, 3H), 4.46 (s, 2H), 4.24 (square, J=8.0 Hz, 4H), 3.83 (s, 3H), 2.49 (s, 3H), 1.40 (p, J=7.0 Hz, 1H), 1, 12 (t, J=8.0 Hz, 6H), 0.29-0.21 (m, 2H), 0.10-0.02 (m, 2H). 36 ¹ H NMR (500 MHz, Chloroform-d) δ 7.46-7.38 (m, 2H), 5.85 (ddt, J=14.7, 12.5, 6.2 Hz, 1H), 5 .06-4.99 (m, 2H), 3.80 (s, 3H), 3.66 (ddt, J=7.1, 5.6, 1.8 Hz, 4H), 2.80 (dt , J=6.2, 1.0 Hz, 2H), 2.54 (s, 3H), 2.03-1.93 (m, 4H), 0.27 (ddd, J=7.0, 4 .2, 2.9 Hz, 2H), 0.12 (tt, J=7.2, 4.3 Hz, 2H). 37 ¹ H NMR (500 MHz, Chloroform-d) δ 7.43-7.24 (m, 7H), 7.26-7.16 (m, 3H), 7.08-6.97 (m, 3H) , 3.90 (s, 3H), 3.66 (t, J=5.2 Hz, 4H), 1.65-1.54 (m, 6H). 38 ¹ H NMR (500 MHz, Chloroform-d) δ 7.51-7.41 (m, 3H), 7.35-7.20 (m, 4H), 5.80 (s, 2H), 3.87 (s, 3H), 2.58 (s, 3H), 2.44 (q, J=8.0 Hz, 2H), 1.11 (t, J=8.0 Hz, 3H). 39 ¹ H NMR (500 MHz, Chloroform-d) δ 7.33-7.17 (m, 6H), 7.06-6.97 (m, 3H), 6.89-6.83 (m, 2H) , 5.80 (s, 2H), 3.90 (s, 3H), 3.78 (s, 3H), 3.34 (s, 3H), 3.22 (t, J=7.6 Hz, 2H), 1.52 (h, J=7.9 Hz, 2H), 0.86 (t, J=8.0 Hz, 3H). 40 ¹ H NMR (500 MHz, Chloroform-d) δ 7.48-7.40 (m, 4H), 7.28 (d, J=4.6 Hz, 2H), 5.80 (s, 2H), 3.90 (s, 3H), 2.94 (s, 6H), 2.66 (q, J=8.0 Hz, 2H), 1.18 (t, J=8.0 Hz, 3H) . 41 ¹ H NMR (500 MHz, Chloroform-d) δ 7.29-7.21 (m, 2H), 7.22-7.16 (m, 2H), 7.15-7.09 (m, 2H) , 5.73 (ddt, J=16.5, 10.1, 6.2 Hz, 1H), 5.29 (s, 1H), 5.31-5.22 (m, 1H), 5.18 -5.07 (m, 1H), 4.46 (d, J=1.2 Hz, 2H), 3.93 (s, 3H), 3.60 (dt, J=6.2, 1.1 Hz, 2H), 3.33 (s, 6H), 2.23-2.13 (m, 5H), 0.99 (t, J=8.0 Hz, 3H). 42 ¹ H NMR (500 MHz, Chloroform-d) δ 7.58-7.49 (m, 3H), 7.48-7.37 (m, 3H), 7.36-7.22 (m, 5H) , 7.00 (d, J=7.5 Hz, 1H), 6.19 (s, 1H), 5.80 (s, 2H), 4.51 (s, 2H), 4.46 (s, 2H), 3.76 (s, 3H), 3.03 (s, 1H). 43 ¹ H NMR (500 MHz, Chloroform-d) δ 7.47 (d, J=7.5 Hz, 1H), 7.42-7.33 (m, 4H), 6.96 (d, J=7 .5 Hz, 1H), 6.11 (s, 1H), 5.80 (s, 2H), 4.68 (s, 1H), 4.51 (s, 2H), 2.46-2.37 (m, 9H). 44 ¹ H NMR (500 MHz, Chloroform-d) δ 7.45 (d, J=7.5 Hz, 1H), 7.38 (d, J=7.5 Hz, 1H), 7.13-7, 06 (m, 4H), 6.83-6.77 (m, 2H), 5.98 (s, 1H), 4.46 (d, J=1.2 Hz, 2H), 3.93 (s , 3H), 3.80 (s, 3H), 2.82 (s, 3H). 45 ¹ H NMR (500 MHz, Chloroform-d) δ 7.63-7.49 (m, 3H), 7.47 (s, 3H), 7.52-7.41 (m, 3H), 7.34 -7.25 (m, 2H), 6.41 (t, J=7.5 Hz, 1H), 6.25 (dd, J=7.5, 1.5 Hz, 1H), 6.21 ( s, 1H), 5.80 (s, 2H), 4.07 (s, 2H). 46 ¹ H NMR (500 MHz, Chloroform-d) δ 7.58-7.48 (m, 3H), 7.50-7.42 (m, 3H), 7.31-7.16 (m, 5H) , 7.11 (d, J=7.5 Hz, 1H), 6.13 (s, 1H), 4.51 (s, 2H), 3.79 (s, 3H), 3.44 (t, J=7.6 Hz, 2H), 2.76-2.68 (m, 4H). 47 ¹ H NMR (500 MHz, Chloroform-d) δ 7.63-7.56 (m, 2H), 7.44-7.38 (m, 1H), 7.32 (s, 1H), 7.37 -7.17 (m, 4H), 5.80 (s, 2H), 4.81 (dd, J=10.0, 1.5 Hz, 1H), 4.58 (dd, J=16.7 , 1.5Hz, 1H), 3.71(s, 3H), 2.97(q, J=8.0Hz, 2H), 1.28(t, J=8.0Hz, 3H) . 48 ¹ H NMR (500 MHz, Chloroform-d) δ 7.58-7.50 (m, 1H), 7.45 (t, J=7.5 Hz, 2H), 7.44-7.35 (m , 4H), 7.34 (d, J=4.6 Hz, 4H), 5.80 (s, 2H), 5.25 (s, 2H), 3.82 (s, 3H). 49 ¹ H NMR (500 MHz, Chloroform-d) δ 7.74 (s, 1H), 7.30-7.20 (m, 2H), 6.63 (dd, J=7.5, 1.5 Hz , 1H), 6.15 (t, J=7.5 Hz, 1H), 6.00 (dd, J=7.4, 1.5 Hz, 1H), 5.80 (s, 2H), 5 .46 (s, 2H), 4.34 (q, J=8.0 Hz, 2H), 3.89 (s, 3H), 2.17 (q, J=8.0 Hz, 2H) , 1.61 (t, J=8.0 Hz, 3H), 1.04 (t, J=8.0 Hz, 3H). fifty ¹ H NMR (500 MHz, Chloroform-d) δ 7.97 (t, J=1.4 Hz, 1H), 7.86-7.78 (m, 2H), 7.75 (dd, J=7 .5, 1.6 Hz, 1H), 7.68 (dt, J=7.7, 2.0 Hz, 1H), 7.54-7.44 (m, 2H), 7.28 (d, J=7.4Hz, 1H), 7.23(dd, J=7.4, 5.6Hz, 1H), 5.80(s, 2H), 3.96(s, 3H), 3, 80 (s, 3H), 2.66 (q, J=8.0 Hz, 2H), 1.23 (t, J=8.0 Hz, 3H). 51 ¹ H NMR (500 MHz, Chloroform-d) δ 7.26-7.17 (m, 2H), 5.80 (s, 2H), 4.34 (sq., J=8.0 Hz, 2H) , 3.92 (s, 3H), 2.21-2.07 (m, 4H), 1.65-1.50 (m, 5H), 1.40 (dtd, J=13.4, 8, 0, 5.5 Hz, 2H), 0.91 (dt, J=35.2, 8.0 Hz, 6H). 52 ¹ H NMR (500 MHz, Chloroform-d) δ 8.09 (dt, J=7.5, 2.0 Hz, 1H), 7.93 (sq., J=1.8 Hz, 1H), 7 .70-7.64 (m, 1H), 7.59-7.50 (m, 2H), 7.40 (dt, J=7.5, 5.7 Hz, 1H), 6.91 (dd , J=8.8, 7.5 Hz, 1H), 5.80 (s, 2H), 2.37 (s, 3H). 53 ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.43 (m, 6H), 7.23-7.17 (m, 1H), 5.80 (s, 2H), 3.11 (s, 3H). 54 ¹ H NMR (500 MHz, Chloroform-d) δ 7.48 (ddd, J=8.1, 6.3, 3.0 Hz, 2H), 7.40-7.32 (m, 8H), 7 .30-7.17 (m, 2H), 5.80 (s, 2H), 3.95 (s, 3H), 3.81 (s, 3H). 55 ¹ H NMR (500 MHz, Chloroform-d) δ 7.48 (ddd, J=8.1, 6.3, 3.0 Hz, 2H), 7.40-7.32 (m, 8H), 7 .30-7.17 (m, 2H), 5.80 (s, 2H), 3.95 (s, 3H), 3.81 (s, 3H). 56 ¹ H NMR (500 MHz, Chloroform-d) δ 7.52-7.45 (m, 3H), 7.40-7.31 (m, 2H), 7.22-7.13 (m, 1H) , 3.16 (s, 3H), 2.72 (s, 2H). 57 ¹ H NMR (500 MHz, Chloroform-d) δ 7.83 (s, 1H), 7.33 (dd, J=7.5, 5.7 Hz, 1H), 7.25 (d, J=7 .4 Hz, 1H), 3.91 (s, 3H), 2.85 (s, 6H), 2.65 (s, 6H). 58 ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.45 (m, 5H), 7.42 (d, J=7.5 Hz, 1H), 7.27 (d, J=7 .5 Hz, 1H), 3.86 (s, 3H), 3.07 (s, 3H), 2.89 (d, J=14.3 Hz, 2H). 59 ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.47 (m, 3H), 7.51-7.41 (m, 2H), 7.30-7.19 (m, 2H) , 3.89 (s, 3H), 3.75 (t, J=4.4 Hz, 2H), 3.15 (s, 3H), 2.72 (t, J=4.4 Hz, 2H) , 2.32 (s, 6H). 60 ¹ H NMR (500 MHz, Chloroform-d) δ 7.50 (s, 5H), 7.27 (t, J=2.4 Hz, 3H), 3.78 (d, J=13.0 Hz, 6H), 3.71 (t, J=4.2 Hz, 2H), 3.49 (t, J=4.2 Hz, 2H), 3.37 (s, 3H), 3.08 (s, 3H). 61 ¹ H NMR (500 MHz, Chloroform-d) δ 8.02 (s, 1H), 7.53-7.43 (m, 5H), 7.29 (d, J=4.9 Hz, 2H), 3.92 (s, 3H), 3.08 (s, 3H), 2.85 (s, 6H). 62 ¹ H NMR (500 MHz, Chloroform-d) δ 7.48 (ddd, J=9.5, 6.2, 2.8 Hz, 2H), 7.41-7.32 (m, 8H), 7 .27 (d, J=7.4 Hz, 1H), 7.19 (dd, J=7.5, 5.5 Hz, 1H), 4.47 (s, 2H), 3.90 (s, 3H), 3.34 (s, 1H). 63 ¹ H NMR (500 MHz, Chloroform-d) δ 7.64-7.58 (m, 2H), 7.46 (tt, J=7.3, 2.1 Hz, 1H), 7.42-7 .35 (m, 2H), 7.34-7.21 (m, 5H), 7.18 (dd, J=7.5, 5.7 Hz, 1H), 7.08 (s, 1H), 4.79 (s, 1H), 3.89 (s, 3H), 2.02 (s, 3H). 64 ¹ H NMR (500 MHz, Chloroform-d) δ 7.54-7.43 (m, 5H), 7.39 (d, J=7.5 Hz, 1H), 7.20 (d, J=7 .5 Hz, 1H), 4.13 (s, 2H), 3.84 (s, 3H), 3.65 (s, 3H), 3.15 (s, 3H), 2.12 (s, 1H ). 65 ¹ H NMR (500 MHz, Chloroform-d) δ 7.63-7.56 (m, 2H), 7.47-7.36 (m, 4H), 7.34-7.23 (m, 3H) , 7.14 (dt, J=8.9, 2.0 Hz, 1H), 3.87 (s, 3H), 3.66 (s, 3H), 2.58 (s, 1H). 66 ¹ H NMR (500 MHz, Chloroform-d) δ 7.50 (s, 4H), 7.50 (s, 1H), 7.53-7.41 (m, 2H), 7.38-7.24 (m, 5H), 4.79 (s, 1H), 3.91 (s, 3H), 3.10 (s, 3H), 2.80 (s, 1H), 2.38 (s, 3H) . 67 ¹ H NMR (500 MHz, Chloroform-d) δ 7.30-7.20 (m, 1H), 3.94 (s, 1H), 2.67 (s, 2H), 1.34 (s, 3H ). 68 ¹ H NMR (500 MHz, Chloroform-d) δ 7.54-7.46 (m, 2H), 7.50 (s, 4H), 7.35-7.26 (m, 2H), 3.89 (s, 3H), 3.81 (s, 3H), 3.10 (s, 3H), 2.14 (d, J=6.8 Hz, 3H). 69 ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.41 (m, 5H), 7.31-7.21 (m, 2H), 3.92 (s, 3H), 3.77 (t, J=4.6 Hz, 4H), 3.57 (t, J=4.6 Hz, 4H), 3.11 (s, 3H). 70 ¹ H NMR (500 MHz, Chloroform-d) δ 7.56-7.43 (m, 8H), 3.86 (s, 3H), 3.65 (s, 3H), 3.02 (s, 3H ). 71 ¹ H NMR (500 MHz, Chloroform-d) δ 7.50 (s, 5H), 7.28 (d, J=7.5 Hz, 1H), 7.21 (dd, J=7.5.5 .5 Hz, 1H), 5.61 (s, 1H), 3.85 (d, J=18.1 Hz, 6H), 3.07 (s, 3H), 2.73 (s, 3H). 72 ¹ H NMR (500 MHz, Chloroform-d) δ 7.50 (s, 5H), 7.41 (d, J=7.5 Hz, 1H), 7.26 (d, J=7.5 Hz, 1H), 3.81 (s, 3H), 3.07 (s, 1H), 3.03 (s, 3H), 2.09 (s, 2H). 73 ¹ H NMR (500 MHz, Chloroform-d) δ 7.52-7.43 (m, 2H), 7.42-7.33 (m, 4H), 7.37 (s, 4H), 7.26 (d, J=7.5 Hz, 1H), 7.14 (dd, J=7.5, 5.7 Hz, 1H), 3.90 (s, 3H), 3.54 (s, 1H) . 74 ¹ H NMR (500 MHz, Chloroform-d) δ 7.65-7.57 (m, 4H), 7.46 (tt, J=7.4, 2.0 Hz, 1H), 7.31-7 .21 (m, 3H), 7.20-7.13 (m, 3H), 4.22-4.11 (m, 4H), 3.91 (s, 3H), 2.53 (s, 1H ), 1.24 (t, J=8.0 Hz, 3H). 75 ¹ H NMR (500 MHz, Chloroform-d) δ 7.50 (d, J=1.3 Hz, 5H), 7.31-7.22 (m, 3H), 3.83 (s, 3H), 3.74 (t, J=4.5 Hz, 2H), 3.62 (sq., J=4.7 Hz, 2H), 3.08 (s, 3H). 76 ¹ H NMR (500 MHz, Chloroform-d) δ 7.60-7.48 (m, 3H), 7.43 (ddd, J=8.8, 6.8, 2.0 Hz, 2H), 7 .34-7.24 (m, 4H), 7.20 (dd, J=7.5, 5.5 Hz, 1H), 3.93 (s, 3H). 77 ¹ H NMR (500 MHz, Chloroform-d) δ 7.53-7.43 (m, 5H), 7.39-7.29 (m, 4H), 7.30-7.20 (m, 3H) , 6.46 (s, 1H), 4.79 (s, 1H), 3.93 (s, 3H), 3.15 (s, 3H). 78 ¹ H NMR (500 MHz, Chloroform-d) δ 7.34-7.26 (m, 2H), 6.48-6.40 (m, 3H), 4.51 (d, J=1.0 Hz , 2H), 3.93 (s, 3H), 3.84 (s, 3H), 3.78 (s, 3H), 2.63 (s, 6H). 79 ¹ H NMR (500 MHz, Chloroform-d) δ 7.88 (dd, J=6.6, 2.8 Hz, 1H), 7.69-7.62 (m, 2H), 7.66-7 .55 (m, 1H), 7.54-7.47 (m, 3H), 7.46-7.38 (m, 3H), 7.29 (d, J=7.5 Hz, 1H), 6.46 (s, 1H), 4.65 (d, J=1.1 Hz, 2H), 3.86 (s, 3H), 2.76 (sq., J=8.0 Hz, 2H) , 2.26 (s, 3H), 1.03 (t, J=8.0 Hz, 3H). 80 ¹ H NMR (500 MHz, Chloroform-d) δ 7.68-7.58 (m, 4H), 7.46 (tt, J=7.4, 2.0 Hz, 1H), 7.39 (tdd , J=5.7, 1.9, 1.0 Hz, 1H), 7.34-7.22 (m, 5H), 7.25-7.15 (m, 3H), 7.11 (td , J=7.5, 2.1 Hz, 1H), 6.46 (s, 1H), 4.65 (d, J=1.1 Hz, 2H), 3.92 (s, 3H). 81 ¹ H NMR (500 MHz, Chloroform-d) δ 7.44 (d, J=7.5 Hz, 1H), 7.26 (d, J=7.5 Hz, 1H), 7.19 (td, J=5.8, 1.2 Hz, 2H), 7.02-6.94 (m, 2H), 6.46 (s, 1H), 4.79 (d, J=1.2 Hz, 2H ), 3.85 (d, J=11.0 Hz, 6H), 2.21-2.06 (m, 3H), 1.04 (d, J=6.8 Hz, 6H), 0.84 (t, J=8.0 Hz, 3H). 82 ¹ H NMR (500 MHz, Chloroform-d) δ 7.64 (dd, J=7.4, 1.6 Hz, 1H), 7.52-7.44 (m, 2H), 7.42-7 .30 (m, 8H), 7.32-7.25 (m, 2H), 6.48-6.40 (m, 2H), 6.34 (dd, J=7.5, 1.6 Hz , 1H), 5.09 (s, 2H), 3.91 (s, 3H). 83 ¹ H NMR (500 MHz, Chloroform-d) δ 7.69 (d, J=7.5 Hz, 2H), 7.58-7.41 (m, 6H), 7.29-7.21 (m , 2H), 7.20-7.13 (m, 3H), 6.46 (s, 1H), 6.39 (dd, J=7.5, 1.5 Hz, 1H), 4.65 ( s, 2H), 3.85 (s, 3H). 84 ¹ H NMR (500 MHz, Chloroform-d) δ 7.54-7.41 (m, 7H), 7.34 (d, J=7.5 Hz, 1H), 7.01 (t, J=7 .4 Hz, 1H), 6.90 (dd, J=7.5, 1.7 Hz, 1H), 6.46 (s, 1H), 4.85 (s, 2H), 3.88 (s , 3H), 3.12 (s, 3H). 85 ¹ H NMR (500 MHz, Chloroform-d) δ 7.57-7.51 (m, 2H), 7.47-7.37 (m, 4H), 7.40-7.27 (m, 4H) , 7.15 (dd, J=7.5, 1.5 Hz, 1H), 7.03-6.94 (m, 2H), 6.46 (s, 1H), 4.70 (s, 2H ), 3.95 (s, 3H). 86 ¹ H NMR (500 MHz, Chloroform-d) δ 7.51 (r, J=3.8, 3.3 Hz, 6H), 7.22 (s, 2H), 7.12 (d, J=7 .5 Hz, 1H), 6.46 (s, 1H), 4.65 (s, 2H), 4.51 (s, 2H), 3.74 (s, 3H), 3.03 (s, 3H ). 87 ¹ H NMR (500 MHz, Chloroform-d) δ 7.50 (dp, J=3.9, 1.9 Hz, 3H), 7.47-7.38 (m, 3H), 7.25 (d , J=7.5 Hz, 1H), 7.01 (d, J=7.5 Hz, 1H), 6.46 (s, 1H), 6.19 (d, J=7.5 Hz, 1H ), 4.58 (s, 2H), 4.51 (s, 2H), 3.80 (s, 3H), 2.98 (s, 3H). 88 ¹ H NMR (500 MHz, Chloroform-d) δ 7.55-7.47 (m, 5H), 7.46-7.40 (m, 2H), 7.17 (dd, J=7.5, 1.6 Hz, 1H), 6.94 (d, J=7.5 Hz, 1H), 6.57 (t, J=7.5 Hz, 1H), 5.76 (s, 2H), 4 .51 (s, 2H), 3.00 (d, J=16.1 Hz, 4H), 2.30 (s, 3H). 89 ¹ H NMR (500 MHz, Chloroform-d) δ 7.55-7.44 (m, 6H), 7.31-7.21 (m, 2H), 6.46 (s, 1H), 6.08 (d, J=7.5 Hz, 1H), 4.58 (s, 2H), 3.93 (s, 3H), 3.12 (s, 3H). 90 ¹ H NMR (500 MHz, Chloroform-d) δ 8.69 (d, J=1.2 Hz, 1H), 8.50 (dd, J=5.0, 1.3 Hz, 1H), 7, 66 (dt, J=8.1, 1.3 Hz, 1H), 7.35-7.27 (m, 2H), 7.23 (dd, J=8.0, 5.0 Hz, 1H) , 6.46 (s, 1H), 4.65 (s, 2H), 3.91 (s, 3H), 2.62 (s, 3H), 2.17 (sq., J=8.0 Hz , 2H), 1.04 (t, J=8.0 Hz, 3H). 91 ¹ H NMR (500 MHz, Chloroform-d) δ 8.62 (dd, J=4.9, 1.3 Hz, 1H), 7.57 (td, J=8.0, 1.2 Hz, 1H ), 7.41 (dd, J=8.0, 1.1 Hz, 1H), 7.30-7.22 (m, 2H), 7.20 (dd, J=7.5, 5.5 Hz, 1H), 6.46(s, 1H), 4.91(s, 2H), 3.90(s, 3H), 3.68(s, 3H), 2.17(q, J= 8.0 Hz, 4H), 1.01 (t, J=8.0 Hz, 6H). 92 ¹ H NMR (500 MHz, Chloroform-d) δ 8.56 (d, J=5.1 Hz, 2H), 7.33 (d, J=5.2 Hz, 2H), 7.26 (d, J=7.5Hz, 1H), 7.17(dd, J=7.5, 5.7Hz, 1H), 6.46(s, 1H), 5.57(s, 2H), 4, 34 (sq., J=8.0 Hz, 2H), 3.92 (s, 3H), 2.63 (s, 3H), 2.11 (t, J=8.0 Hz, 2H), 1 .65-1.54 (m, 3H), 1.57-1.48 (m, 2H), 0.92 (t, J=8.1 Hz, 3H). 93 ¹ H NMR (500 MHz, Chloroform-d) δ 8.49 (dd, J=5.0, 1.2 Hz, 1H), 7.32-7.22 (m, 2H), 7.23-7 .16 (m, 2H), 6.46 (s, 1H), 4.91 (s, 2H), 3.93 (s, 3H), 2.62 (s, 3H), 2.28 (s, 3H), 2.17 (sq., J=8.0 Hz, 2H), 1.04 (t, J=8.0 Hz, 3H). 94 ¹ H NMR (500 MHz, Chloroform-d) δ 7.82-7.73 (m, 2H), 7.72 (dt, J=7.5, 1.6 Hz, 1H), 7.68 (t , J=1.5 Hz, 1H), 7.58 (dd, J=7.4, 1.5 Hz, 1H), 7.41 (dtd, J=26.1, 7.4, 1.6 Hz, 2H), 7.33-7.26(m, 2H), 6.46(s, 1H), 4.90(s, 2H), 3.94(s, 3H), 2.59(s , 3H), 1.69 (hept, J=6.9 Hz, 1H), 1.07 (d, J=6.8 Hz, 6H). 95 ¹ H NMR (500 MHz, Chloroform-d) δ 8.83 (dd, J=7.5, 1.5 Hz, 1H), 8.35 (dd, J=7.5, 1.4 Hz, 1H ), 8.01 (dd, J=7.4, 1.5 Hz, 1H), 7.71-7.63 (m, 3H), 7.66-7.57 (m, 2H), 7, 56-7.48 (m, 2H), 7.39-7.31 (m, 2H), 7.28 (d, J=7.5 Hz, 1H), 7.25-7.14 (m, 5H), 6.46 (s, 1H), 4.80 (s, 2H), 3.96 (s, 3H). 96 ¹ H NMR (500 MHz, Chloroform-d) δ 8.78 (s, 2H), 8.14 (d, J=7.5 Hz, 1H), 7.92 (d, J=1.5 Hz, 1H), 7.75 (dd, J=7.5, 1.5 Hz, 1H), 7.65-7.53 (m, 3H), 7.45 (t, J=7.5 Hz, 2H ), 7.35 (tt, J=7.3, 2.2 Hz, 1H), 7.28 (d, J=7.5 Hz, 1H), 7.28-7.18 (m, 3H) , 7.18 (dd, J=7.8, 2.1 Hz, 2H), 6.46 (s, 1H), 4.79 (s, 2H), 3.92 (s, 3H). 97 ¹ H NMR (500 MHz, DMSO-d 6 ) δ 7.65-7.59 (m, 1H), 7.41 (dd, J=8.7, 1.6 Hz, 1H), 4.12 ( t, J=7.2 Hz, 2H), 3.89 (s, 3H), 2.08-2.01 (m, 3H), 1.29-1.22 (m, 3H). 98 ¹ H NMR (500 MHz, DMSO-d 6 ) δ 8.91 (s, 1H), 7.80-7.75 (m, 2H), 7.64 (t, J=8.1 Hz, 1H) , 7.60-7.54 (m, 1H), 7.52 (dd, J=8.2, 6.6 Hz, 2H), 7.42 (dd, J=8.7, 1.6 Hz , 1H), 3.90 (s, 3H). 99 ¹ H NMR (500 MHz, DMSO-d 6 ) δ 7.61 (t, J=8.0 Hz, 1H), 7.41 (dd, J=8.6, 1.6 Hz, 1H), 3 .89 (s, 3H), 1.98 (d, J=1.5 Hz, 3H), 1.11 (d, J=1.5 Hz, 9H). 100 ¹ H NMR (500 MHz, Chloroform-d) δ 7.60 (dd, J=7.5, 5.7 Hz, 1H), 7.41 (dd, J=8.9, 2.0 Hz, 1H ), 7.13 (dd, J=7.5, 2.0 Hz, 1H), 5.80 (s, 2H), 2.60 (s, 6H). 101 ¹ H NMR (500 MHz, Chloroform-d) δ 7.84 (s, 1H), 7.58-7.50 (m, 1H), 7.47-7.39 (m, 2H), 7.36 -7.30 (m, 2H), 7.27 (dd, J=7.5, 5.7 Hz, 1H), 7.12 (d, J=7.5 Hz, 1H), 5.80 ( s, 2H). 102 ¹ H NMR (500 MHz, Chloroform-d) δ 7.36 (dd, J=7.5, 5.7 Hz, 1H), 7.28 (dd, J=7.5, 5.7 Hz, 1H ), 5.80 (s, 2H), 2.66 (s, 6H). 103 ¹ H NMR (500 MHz, Chloroform-d) δ 7.43 (dd, J=7.5, 5.7 Hz, 1H), 7.34 (d, J=7.5 Hz, 1H), 5, 80 (s, 2H), 3.89 (s, 3H), 2.11 (t, J=5.6 Hz, 4H), 1.72-1.56 (m, 6H). 104 ¹ H NMR (500 MHz, DMSO-d 6 ) δ 7.61 (t, J=8.1 Hz, 1H), 7.41 (d, J=8.6 Hz, 1H), 3.89 (s , 3H), 2.49-2.47 (m, 4H), 1.76-1.71 (m, 4H).

Examples of representative compounds are as follows:

1. Obtaining compound 98:

Device construction: 50 ml single neck round bottom flask, stirring element and constant temperature mixer.

Compound a (0.4 g, 1.2 mmol, 1.0 eq.), PyBOP (0.69 g, 1.32 mmol, 1.1 eq.) and Et ₃ N (0.16 g, 1.0 eq.) 6 mmol, 1.3 eq.) was successively added to 8 ml of DCM and the reaction solution was stirred at room temperature for 30 minutes, followed by the addition of compound b (0.16 g, 1.3 mmol, 1.1 eq.). Then, the reaction solution was stirred for 12 hours. TLC analysis showed that the reaction was complete. The reaction solution was poured into 10 ml of water and the mixture was separated, the aqueous phase was extracted with 10 ml of DCM three times and the organic phase was dried, evaporated to dryness under reduced pressure and separated by column chromatography to obtain Compound 98 (0.35 g, 67% yield) ( white solid).

2. Obtaining compound 99:

Device design: 50 ml single neck round bottom flask, stirrer and constant temperature magnetic stirrer.

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.) was successively added to 10 ml of ACN and the reaction solution was stirred at room temperature for 30 minutes, followed by the addition of compound c (0.15 g, 1.3 mmol, 1.1 eq.). Then, the reaction solution was stirred for 12 hours. TLC analysis showed that the reaction was complete. The reaction solution was poured into 10 ml of water and the mixture was separated, the aqueous phase was extracted with 10 ml of ethyl acetate three times and the organic phase was dried, evaporated to dryness under reduced pressure and separated by column chromatography to obtain Compound 99 (0.38 g, 74% yield) ( white solid).

The method for producing the compound of the invention will be explained in detail in the following program and embodiment. The starting materials are commercially available, or they are prepared in a known manner, described in the literature or indicated in the way. Those skilled in the art will appreciate that the compound of the present invention may also be synthesized by other synthetic routes. Although the starting materials and reaction conditions in the synthesis route are explained in detail below, they can still be easily replaced by other similar substances and conditions. The isomer of the compound, for example, which is obtained by changing the method of obtaining according to the present invention, is included in the scope of the present invention. In addition, the following production method can be further modified according to the disclosure of the present invention using a conventional chemical method known to those skilled in the art, such as protecting a suitable group during a reaction, etc.

The following application method can be used to better understand the production method of the present invention. Specific substances, class and conditions have been determined as a further explanation of the present invention, and not as a limitation of its reasonable scope. The reagents for the following synthetic compound shown in the table can be purchased from the market or easily obtained by those skilled in the art.

Examples of representative compounds are shown below.

Assessment of biological activity:

The standard for assessing the level of activity aimed at the destruction of harmful plants (i.e. the degree of growth inhibition) is as follows:

Level 10: total destruction;

Level 9: growth inhibition greater than 95%;

Level 8: growth inhibition greater than 90%;

Level 7: growth inhibition greater than 80%;

Level 6: growth inhibition greater than 70%;

Level 5: growth inhibition greater than 60%;

Level 4: growth inhibition greater than 50%;

Level 3: growth inhibition greater than 20%;

Level 2: growth inhibition 5-20%;

Level 1: growth inhibition less than 5%;

Level 0: no effect.

The percentages of growth inhibition indicated above are the percentages of inhibition on a wet weight basis.

Post-emergence test experiment: Seeds of monocots and dicots, as well as seeds of major crops (e.g., wheat, corn, rice, soybean, cotton, oilseed rape, millet, and sorghum) were placed in a plastic pot with soil, then covered with 0.5-2 cm soil and seeds were allowed to grow in a good greenhouse environment. The test plants were treated at the 4-5 leaf stage 2-3 weeks after sowing. The test compounds of the invention were respectively dissolved in acetone, then Tween-80 was added and diluted with a certain amount of water to obtain solutions with certain concentrations. The solution was sprayed onto the plants using a sprayer. Plants were grown in a greenhouse for 3 weeks. The results of experiments to evaluate the effect of weed control after 3 weeks are presented in Table 3 and Table 4.

Table 3
Experiment to evaluate the effect of weed control in the post-emergence stage Connection No. Descurainia sophia Galium aparine L. Abutilon theophrasti Sagittaria trifolia L. Monochoria vaginalis one ten ten ten ten ten 2 ten ten ten ten ten 3 ten ten ten ten ten four ten ten ten ten ten 5 ten ten ten ten ten 6 ten ten ten ten ten 7 ten ten ten ten ten eight ten ten ten ten ten 9 ten ten ten ten ten ten ten ten ten ten ten eleven ten ten ten ten ten 12 ten ten ten ten ten 13 ten ten ten ten ten fourteen ten ten ten ten ten fifteen ten ten ten ten ten 16 ten ten ten ten ten 17 ten ten ten ten ten eighteen ten ten ten ten ten 19 ten ten ten ten ten twenty ten ten ten ten ten 21 ten ten ten ten ten 22 ten ten ten ten ten 23 ten ten ten ten ten 24 ten ten ten ten ten 25 ten ten ten ten ten 26 ten ten ten ten ten 27 ten ten ten ten ten 28 ten ten ten ten ten 29 ten ten ten ten ten thirty ten ten ten ten ten 31 ten ten ten ten ten 32 ten ten ten ten ten 33 ten ten ten ten ten 34 ten ten ten ten ten 35 ten ten ten ten ten 36 ten ten ten ten ten 37 ten ten ten ten ten 38 ten ten ten ten ten 39 ten ten ten ten ten 40 ten ten ten ten ten 41 ten ten ten ten ten 42 ten ten ten ten ten 43 ten ten ten ten ten 44 ten ten ten ten ten 45 ten ten ten ten ten 46 ten ten ten ten ten 47 ten ten ten ten ten 48 ten ten ten ten ten 49 ten ten ten ten ten fifty ten ten ten ten ten 51 ten ten ten ten ten 52 ten ten ten ten ten 53 ten ten ten ten ten 54 ten ten ten ten ten 55 ten ten ten ten ten 56 ten ten ten ten ten 57 ten ten ten ten ten 58 ten ten ten ten ten 59 ten ten ten ten ten 60 ten ten ten ten ten 61 ten ten ten ten ten 62 ten ten ten ten ten 63 ten ten ten ten ten 64 ten ten ten ten ten 65 ten ten ten ten ten 66 ten ten ten ten ten 67 ten ten ten ten ten 68 ten ten ten ten ten 69 ten ten ten ten ten 70 ten ten ten ten ten 71 ten ten ten ten ten 72 ten ten ten ten ten 73 ten ten ten ten ten 74 ten ten ten ten ten 75 ten ten ten ten ten 76 ten ten ten ten ten 77 ten ten ten ten ten 78 ten ten ten ten ten 79 ten ten ten ten ten 80 ten ten ten ten ten 81 ten ten ten ten ten 82 ten ten ten ten ten 83 ten ten ten ten ten 84 ten ten ten ten ten 85 ten ten ten ten ten 86 ten ten ten ten ten 87 ten ten ten ten ten 88 ten ten ten ten ten 89 ten ten ten ten ten 90 ten ten ten ten ten 91 ten ten ten ten ten 92 ten ten ten ten ten 93 ten ten ten ten ten 94 ten ten ten ten ten 95 ten ten ten ten ten 96 ten ten ten ten ten 97 ten ten ten ten ten 98 ten ten ten ten ten 99 ten ten ten ten ten 100 ten ten ten ten ten 101 ten ten ten ten ten 102 ten ten ten ten ten 103 ten ten ten ten ten 104 ten ten ten ten ten Control Compound A 6 four 5 5 6 Note: The application rate was 45 g/ha of active ingredient, with 450 kg/ha of added water.

(CN102675218B).Control Compound A:

(CN102675218B).

Table 4
Experiment to evaluate the effect of weed control in the post-emergence stage No. Corn Rice Sagittaria trifolia L. Veronica didyma Tenore Rorippa indica Leptochloa chinensis Echinochloa crusgalli 9 one one ten ten 6 7 ten 99 one one ten ten 7 eight ten Control Compound A 3 2 5 3 6 2 3 Control Compound B eight 5 ten 9 3 5 eight Control Compound C 7 5 ten 2 2 3 eight Note: The application rate was 30 g/ha of active ingredient, with 450 kg/ha of added water.

; Контрольное Соединение C: галауксифен-метил.Control Compound B:

; Control Compound C: galauxifen-methyl.

According to Table 3 and Table 4, compared with the control compounds, the crop safety and herbicidal activity of the compounds of the present invention are greatly improved by changing the original ring structure, substituent as well as the type of carboxyl derivative, in particular, the compounds of the present invention have good selectivity in against important crops such as corn, rice, etc., while the control compounds have poor selectivity for major crops. This demonstrates that the present invention has excellent technical effects.

Pre-emergence test experiment:

Seeds of monocots and dicots and major crops (eg, wheat, corn, rice, soybean, cotton, oilseed rape, millet, and sorghum) were placed in a plastic pot loaded with soil and covered with 0.5-2 cm of soil. The test compounds of the present invention were dissolved in acetone, then Tween-80 was added, diluted with some water to reach a certain concentration and sprayed immediately after inoculation. The resulting seeds were incubated for 4 weeks in a greenhouse after spraying. The test results were observed after 3 weeks. It was observed that the herbicides of the present invention mainly had an excellent effect at a dose of 250 g/ha, especially against weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Abutilon theophrasti, etc., and many compounds had good selectivity against corn. , wheat, rice, soybean, oilseed rape, etc.

Experiment has shown that the compounds of the present invention generally have good weed control efficiency, especially with respect to main grass weeds such as Echinochloa crusgalli, Digitaria sanguinalis and Setaria viridis, etc., and main broadleaf weeds such as Abutilon theophrasti, Rorippa indica and Bidens pilosa, which are widely distributed in corn, rice and wheat fields, and have excellent commercial value. First of all, it should be noted that the compound of the present invention has extremely high activity against ALS inhibitor resistant broadleaf weeds such as Rorippa indica, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine and Stellaria media, etc. d.

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

The soil from the rice field was loaded into a 1/1,000,000 ha pot. Seeds of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartite and Sagittaria trifolia L. were sown and carefully covered with soil, and then left in a greenhouse with a water supply of 0.5-1 cm. Sagittaria trifolia L. tuber was planted the next day or 2 days later. Thereafter, it was maintained at a water reserve of 3-4 cm. Weeds were treated by dropping WP or SC dilutions in water, obtained in accordance with the usual method, of the compounds of the present invention by pipetting evenly until the indicated effective amount was reached when Echinochloa crusgalli, Scirpus juncoides and Bidens tripartite reached the 0.5 leaf stage and Sagittaria trifolia L. reached the time point of the first leaf stage.

In addition, the soil from the rice field loaded into 1/1000000 ha pot was leveled to keep the water supply at a depth of 3-4 cm. The next day, rice in the third leaf stage (Japanese rice) was transplanted to a depth of 3 cm. of the present invention was carried out in the same way 5 days after transplantation.

The fertility status of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartite and Sagittaria trifolia L. 14 days after treatment with the compound of the present invention and the fertility status of rice 21 days after treatment with the compound of the present invention, respectively, were assessed with the naked eye. The weed control effect was evaluated according to a standard activity level of 1-10. Many of the compounds have been found to have excellent activity and selectivity.

Note: The seeds of Echinochloa crusgalli, Scirpus juncoides, Sagittaria trifolia L. and Bidens tripartite were collected from Heilongjiang province in China. Tests have shown that weeds are resistant to the usual rate of application of pyrazosulfuron-ethyl.

At the same time, after several tests, it was found that the compound of the present invention has good selectivity for many grasses, such as Japanese zoisia, Bermuda grass, high fescue, bluegrass, ryegrass, sea paspalum, etc., and is able to control many important grass and broadleaf weeds. The compounds also show excellent selectivity and commercial value in tests on soybean, cotton, sunflower, potato, horticultural and vegetable crops in various herbicide applications.

Claims (84)

1. Substituted pyrimidinylformyl oxime derivative of general formula I:

where R ₁ and R ₂ are independently H, halo, cyano, nitro, C1-C8 alkyl, halo, C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, benzyl, phenoxy, phenylthio, or a group represented by the formula -COR ₅ , wherein said "substituted" refers to substituted with one group selected from halo, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl , C3-C8 cycloalkyl, C1-C8 alkoxy, C2-C8 alkenoxy, C1-C8 alkylthio and amino which is optionally substituted with C1-C8 alkyl, phenyl, phenoxy or C1-C8 acyl; where R ₅ is C1-C8 alkyl, C1-C8 alkoxy, C2-C8 alkenoxy, C1-C8 alkylthio, phenoxy, phenylmethoxy, 5-membered heteroarylmethoxy containing a nitrogen atom, or amino which is optionally substituted with C1-C8 alkyl, phenyl , phenyl C1-C8 alkyl, phenyl C1-C8 alkyl substituted with one substituent selected from C1-C8 alkyl, halogen and C1-C8 alkoxy, or 5-membered heteroaryl C1-C8 alkyl containing an oxygen atom; or R ₁ and R ₂ are linked to form a 5- or 6-membered saturated ring; X is C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, halo, C2-C8 alkenyl, or C2-C8 alkynyl; Y is nitro or NR ₃ R ₄ where R ₃ is H, C1-C8 alkyl, -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N=CR ₁₇ R ₁₈ where C1 -C8 alkyl is optionally substituted with one or two R ₁₁ groups; R ₄ is H, C1-C8 alkyl or —COR ₁₂ where C1-C8 alkyl is optionally substituted with one or two R ₁₁ groups; or NR ₃ R ₄ is N=CR ₂₁ NR ₂₂ R ₂₃ or a 5- or 6-membered saturated or aromatic ring which optionally additionally contains an oxygen atom; where R ₁₁ is independently hydroxy, C1-C8 alkoxy, di C1-C8 alkylamino, C1-C8 alkoxycarbonyl, phenyl, naphthyl or a 5-10 membered heteroaryl containing 1-2 atoms selected from an oxygen atom, a sulfur atom and an atom nitrogen, where phenyl, naphthyl and heteroaryl are independently unsubstituted or substituted with 1-3 groups selected from nitro, C1-C8 alkyl, C1-C8 alkoxy and halogen; R ₁₂ is C1-C8 alkyl or C1-C8 alkoxy; R ₁₃ is H, C1-C8 alkyl, benzyl or CHR ₃₁ C(O)OR ₃₂ ; R ₃₁ is H; R ₃₂ is H; R ₁₄ is C1-C8 alkyl; R ₁₅ is H or C1-C8 alkylacyl; R ₁₆ is H; R ₁₇ is H or C1-C8 alkyl; R ₁₈ is H or C1-C8 alkyl; R ₂₁ is H; R ₂₂ and R ₂₃ are each independently C1-C8 alkyl; A is halo or amino; B is hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino or di C1-C8 alkylamino, where C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino and di C1-C8 alkylamino independently are unsubstituted or substituted with halogen; C is halo or halo C1-C8 alkyl. 2. A substituted pyrimidinylformyl oxime derivative according to claim 1, which is characterized in that R ₁ and R ₂ are independently H, cyano, C1-C8 alkyl, halo, C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, unsubstituted or substituted phenyl, unsubstituted or substituted naphthyl, benzyl, phenoxy, phenylthio or a group represented by the formula -COR ₅ where R ₅ is C1-C8 alkyl, C1-C8 alkoxy, C2-C8 alkoxy, C1-C8 alkylthio, phenoxy, phenylmethoxy, 5-membered heteroarylmethoxy containing a nitrogen atom, or amino which is optionally substituted with C1-C8 alkyl, phenyl, phenyl C1-C8 alkyl, phenyl C1-C8 alkyl substituted with one substituent selected from C1-C8 alkyl, halogen and C1-C8 alkoxy, or 5 -membered heteroaryl C1-C8 alkyl containing an oxygen atom; where said “substituted” means a substitution with one group selected from halo, cyano, nitro, C1-C8 alkyl, halo, C1-C8 alkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C2-C8 alkoxy, C1-C8 alkylthio, and amino , which is optionally substituted with C1-C8 alkyl, phenyl, phenoxy, or C1-C8 acyl; X is C1-C8 alkyl, C1-C8 alkoxy, C1-C8 alkylthio, halogen, C2-C8 alkenyl, or C2-C8 alkynyl; Y is nitro or NR ₃ R ₄ where R ₃ is H, C1-C8 alkyl, -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N=CR ₁₇ R ₁₈ where C1 -C8 alkyl is optionally substituted with one or two R ₁₁ groups; R ₄ is H, C1-C8 alkyl or —COR ₁₂ where C1-C8 alkyl is optionally substituted with one or two R ₁₁ groups; or NR ₃ R ₄ is N=CR ₂₁ NR ₂₂ R ₂₃ ,

or

; where R ₁₁ is independently hydroxy, C1-C8 alkoxy, diC1-C8 alkylamino, C1-C8 alkoxycarbonyl, phenyl, naphthyl,

or

where phenyl, naphthyl,

and

are independently unsubstituted or substituted with 1-3 groups selected from halo, C1-C8 alkyl, C1-C8 alkoxy, and nitro; R ₁₂ is C1-C18 alkyl or C1-C8 alkoxy; R ₁₃ is H, C1-C8 alkyl, benzyl or CHR ₃₁ C(O)OR ₃₂ ; R ₃₁ is H; R ₃₂ is H; R ₁₄ is C1-C8 alkyl; R ₁₅ is H or C1-C8 alkylacyl; R ₁₆ is H; R ₁₇ is H or C1-C8 alkyl; R ₂₁ is H; R ₂₂ and R ₂₃ are each independently C1-C8 alkyl; A is halo or amino; B is hydrogen, halogen, C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino or diC1-C8 alkylamino, where C1-C8 alkoxy, C1-C8 alkylthio, C1-C8 alkylamino and diC1-C8 alkylamino are independently unsubstituted or substituted with halogen; C is halo or halo C1-C8 alkyl. 3. A substituted pyrimidinylformyl oxime derivative according to claim 1 or 2, which is characterized in that R ₁ and R ₂ are independently hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, cyano, C1-C6 alkoxycarbonyl, or phenyl, wherein said phenyl is unsubstituted or substituted with one group selected from halo, halo C1 -C6 alkyl, C1-C6 alkyl and C1-C6 alkoxy; X is C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, halogen, C2-C6 alkenyl, or C2-C6 alkynyl; Y is nitro or NR ₃ R ₄ where R ₃ is H, C1-C6 alkyl, -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N=CR ₁₇ R ₁₈ where C1 -C6 alkyl is optionally substituted with one or two R ₁₁ groups; R ₄ is H, C1-C6 alkyl or —COR ₁₂ where C1-C6 alkyl is optionally substituted with one or two R ₁₁ groups; or NR ₃ R ₄ is N=CR ₂₁ NR ₂₂ R ₂₃ ,

or

; where R ₁₁ is independently hydroxy, C1-C6 alkoxy, diC1-C6 alkylamino, C1-C6 alkoxycarbonyl, phenyl, naphthyl,

or

where phenyl, naphthyl,

and

are independently unsubstituted or substituted with 1-3 groups selected from halo, C1-C6 alkyl, C1-C6 alkoxy and nitro; R ₁₂ is C1-C4 alkyl or C1-C6 alkoxy; R ₁₃ is H, C1-C6 alkyl, benzyl or CHR ₃₁ C(O)OR ₃₂ ; R ₃₁ is H; R ₃₂ is H; R ₁₄ is C1-C6 alkyl; R ₁₅ is H or C1-C6 alkylacyl; R ₁₆ is H; R ₁₇ is H or C1-C6 alkyl; R ₁₈ is H or C1-C6 alkyl; R ₂₁ is H; R ₂₂ and R ₂₃ are independently C1-C6 alkyl; A is halo or amino; B is hydrogen, halogen, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino or diC1-C6 alkylamino, where C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylamino and diC1-C6 alkylamino are independently unsubstituted or substituted with halogen; C is halo or halo C1-C6 alkyl. 4. Substituted pyrimidinylformyl oxime derivative according to any one of paragraphs. 1-3, which differs in that R ₁ and R ₂ are independently hydrogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, cyano, C1-C4 alkoxycarbonyl, or phenyl, wherein said phenyl is unsubstituted or substituted with one group selected from halo, halo C1 -C4 alkyl, C1-C4 alkyl or C1-C4 alkoxy; X is C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, halogen, C2-C4 alkenyl, or C2-C4 alkynyl; Y is nitro or NR ₃ R ₄ where R ₃ is H, C1-C4 alkyl, -COR ₁₂ , nitro, OR ₁₃ , SO ₂ R ₁₄ , NR ₁₅ R ₁₆ , N=CR ₁₇ R ₁₈ where C1 -C4 alkyl is optionally substituted with 1-2 R ₁₁ groups; R ₄ is H, C1-C4 alkyl or —COR ₁₂ where C1-C4 alkyl is optionally substituted with one or two R ₁₁ groups; or NR ₃ R ₄ is N=CR ₂₁ NR ₂₂ R ₂₃ ,

or

; where R ₁₁ is independently hydroxy, C1-C4 alkoxy, diC1-C4 alkylamino, C1-C4 alkoxycarbonyl, phenyl, naphthyl,

or

where phenyl, naphthyl,

and

are independently unsubstituted or substituted with 1-3 groups selected from halo, C1-C4 alkyl, C1-C4 alkoxy, and nitro; R ₁₂ is C1-C8 alkyl or C1-C4 alkoxy; R ₁₃ is H, C1-C4 alkyl, benzyl or CHR ₃₁ C(O)OR ₃₂ ; R ₃₁ is H; R ₃₂ is H; R ₁₄ is C1-C4 alkyl; R ₁₅ is H or C1-C4 alkylacyl; R ₁₆ is H; R ₁₇ is H or C1-C4 alkyl; R ₁₈ is H or C1-C4 alkyl; R ₂₁ is H; R ₂₂ and R ₂₃ are independently C1-C4 alkyl; A is halo or amino; B is hydrogen, halogen, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino or diC1-C4 alkylamino, where C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino and diC1-C4 alkylamino are independently unsubstituted or substituted with halogen; C is halo or halo C1-C4 alkyl. 5. A substituted pyrimidinylformyl oxime derivative according to claim 1, which is characterized in that R ₁ and R ₂ are independently hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, methylthio, ethylthio, cyano, methoxycarbonyl, ethoxycarbonyl or phenyl, wherein said phenyl is unsubstituted or substituted with one group, selected from halogen, CF ₃ , methyl, ethyl, propyl, isopropyl, n-butyl, t-butyl, cyclopropyl, methoxy and ethoxy; X represents chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl; Y is NH ₂ , NHMe, N(Me) ₂ ,

or

; A is fluorine, chlorine or amino; B represents hydrogen, fluorine, chlorine, methoxy, ethoxy or methylthio, where methoxy, ethoxy and methylthio are unsubstituted or substituted with fluorine; C represents fluorine, chlorine or trifluoromethyl. 6. A substituted pyrimidinylformyl oxime derivative according to claim 1, which is characterized in that its structural formula is any of the following:

7. The method of obtaining a substituted pyrimidinylformyl oxime derivative according to any one of paragraphs. 1-6, which includes the following stages: the implementation of the interaction of a compound of general formula II and a compound of general formula III to obtain a substituted pyrimidinylformyl oxime derivative of general formula I, where the chemical reaction scheme is as follows:

. 8. The method of claim 7 wherein said reaction is carried out under the action of a base and a condensing agent and in an aprotic solvent. 9. The method according to p. 7, where the temperature of the specified reaction is from 0°C to 90°C. 10. The method according to p. 8, where the specified solvent is one solvent or several mixed solvents selected from dichloromethane, dichloroethane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, toluene and xylene; said base is one or more bases selected from triethylamine, trimethylamine, DIPEA and DBU; or said condensing agent is PyBop, HATU or HOBt-EDCI. 11. Herbicidal composition, which is characterized in that the composition includes a herbicidally effective amount of a substituted pyrimidinylformyl oxime derivative according to any one of paragraphs. 1-6 and a formulation aid. 12. A method of controlling a harmful plant, characterized in that it includes applying a herbicidally effective amount of a substituted pyrimidinylformyl oxime derivative according to any one of paragraphs. 1-6 or the herbicidal composition according to claim 11 on a harmful plant or on an area with a harmful plant. 13. The use of a substituted derivative of pyrimidinylformyl oxime according to any one of paragraphs. 1-6 or a herbicidal composition according to claim 11 for controlling a harmful plant.