WO2020114212A1 - 4-(3-heterocyclyl-1-benzoyl) pyrazole compound or salt thereof, preparation method therefor, herbicide composition thereof and use thereof - Google Patents

Abstract

The present invention relates to the technical field of pesticides, and relates in particular to a 4-(3-heterocyclyl-1-benzoyl) pyrazole compound or a salt thereof, a preparation method therefor, a herbicide composition thereof and a use thereof. The structure of the compound is represented by formula I: wherein X represents alkyl or cycloalkyl; Y represents a hydrogen atom, alkyl not containing or containing halogen, alkenyl, alkynyl, unsubstituted or alkyl-substituted cycloalkyl; Z represents alkyl, halogen, cyano, alkoxy, alkylthio, and alkylsulfonyl; and Q represents unsubstituted or substituted pyrazolyl. The compound, the salt thereof and herbicide composition thereof have more prominent herbicidal activity and crop safety.

Description

4-(3-heterocyclic-1-benzoyl)pyrazole compound or its salt, preparation method, herbicide composition and use Technical field

The invention belongs to the technical field of pesticides, and specifically relates to a 4-(3-heterocyclic-1-benzoyl)pyrazole compound or a salt thereof, a preparation method, a herbicide composition and use.

technical background

Weed control is a crucial link in the process of achieving efficient agriculture. Although there are many types of herbicides on the market, there are many studies on pyrazole herbicides. For example, CN1250447A and CN1104429C introduced a series of structural formulas that include A pyrazole compound with a pyrazole ring. However, due to the continuous expansion of the market, the resistance of weeds, the service life of drugs and the economics of drugs, and the increasing attention paid to the environment, scientists need to continue to research and develop new high-efficiency, safe, economic and different Variety of herbicides in action.

Summary of the invention

In order to design and synthesize herbicide compounds with higher drug resistance, broader activity spectrum and better safety, based on the research of pyrazole herbicide compounds, through molecular design and optimization, the present invention has synthesized a class of The 4-(3-heterocyclic-1-benzoyl)pyrazole compound containing two pyrazole rings in the novel structure used as the active component of the herbicide has more outstanding activity and crop safety.

To achieve the above objectives, the technical solutions adopted by the present invention are as follows:

A 4-(3-heterocyclyl-1-benzoyl)pyrazole compound or its salt having the structure of formula I:

among them,

X represents alkyl, cycloalkyl;

Y represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an unsubstituted or alkyl-substituted cycloalkyl group that does not contain or contains a halogen;

Z represents alkyl, halogen, cyano, alkoxy, alkylthio, alkylsulfonyl;

Q represents unsubstituted or substituted pyrazolyl.

Preferably, X represents C _1-8 alkyl, C _3-8 cycloalkyl;

Y represents a hydrogen atom, a C _1-8 alkyl group containing no or halogen, a C _2-8 alkenyl group, a C _2-8 alkynyl group, an unsubstituted C _3-8 cycloalkane substituted with a C _1-8 alkyl group base;

Z represents C _1-8 alkyl, halogen, cyano, C _1-8 alkoxy, C _1-8 alkylthio, C _1-8 alkylsulfonyl;

Q stands for

among them,

R ₁ and R ₂ independently represent hydrogen, cyano, thiocyano, cyanoalkyl, nitro, halogen, mercapto, OR ₄ , R ₅ , SO _m -R ₅ , SO ₂ -OR ₄ , NR ₆ -SO ₂ -R ₅ , O-SO ₂ -R ₅ , NR ₆ -(C=O)-R ₄ , NR ₆ -(C=O)-OR ₄ , -(C=O)-NR ₆ -OR ₄ , NR ₇ R ₈ , SO ₂ -NR ₇ R ₈ , -(C=O)-NR ₇ R ₈ , O-(C=O)-OR ₄ , NR ₆ -(C=O)-NR ₇ R ₈ , O-(C=O)-NR ₇ R ₈ , -alkyl-NR ₆ -(C=O)-R ₄ , -alkyl-SO ₂ -OR ₄ , -alkyl-NR ₆ -SO ₂ -R ₅ , -alkyl-O-SO ₂ -R ₅ , -alkyl-SO ₂ -NR ₇ R ₈ , SO ₂ -NR ₇ -alkyl-S(O) _n -R ₅ , -alkyl- _{OR 4, (C = O)} -R 4, (C = O) -OR 4, O- (C = O) -R 4, - alkyl _{- (C = O) -R 4} , - alkyl - ( C=O)-OR ₄ , -alkyl-O-(C=O)-R ₄ , (C=S)-R ₄ , (C=S)-OR ₄ , (C=S)-SR ₅ , (C=O)-SR ₅ , S-(C=O)-R ₄ , S-(C=S)-R ₄ , O-(C=S)-R ₄ , -alkyl-(C=S )-R ₄ ,-alkyl-(C=S)-OR ₄ ,-alkyl-(C=O)-SR ₅ ,-alkyl-(C=S)-SR ₅ ,-alkyl-S- (C=O)-R ₄ ,-alkyl-O-(C=S)-R ₄ ,-alkyl-S-(C=S)-R ₄ ,-alkyl-SO _m -R ₅ ,- O-alkyl-NR ₇ R ₈ , -S-alkyl-NR ₇ R ₈ , -alkyl-O-alkyl-NR ₇ R ₈ , -alkyl-S-alkyl-NR ₇ R ₈ ,- Alkyl-(C=O) _n -NR ₇ R ₈ , -alkyl-(C=S) _n -NR ₇ R ₈ , -NH-alkyl-NR ₇ R ₈ , P(O)(OR ₉ ) ₂ , CH ₂ P(O)(OR ₉ ) ₂ ;

R ₃ , R ₆ , R ₇ and R ₈ independently represent hydrogen, amino, nitro, cyano, mercapto, halogen, alkylamino, dialkylamino, OR ₁₁ , -alkyl-OR ₁₁ , SO _q -R ₁₀ , -alkyl-SO _q -R ₁₀ , (C=O)-R ₁₁ , (C=O)-OR ₁₁ , R ₁₀ , alkylthio, alkylaminocarbonyl, alkylcarbonylalkyl, alkyl Oxycarbonylalkyl, alkylaminocarbonylalkyl, alkylcarbamoyl, alkoxyaminocarbonyl, alkylacyloxy, alkylthiocarbonyl, trialkylsilyl, dialkylphosphono; or R ₇ R ₈ N- represents a six-membered heterocyclic group

R ₉ independently represents alkyl;

R ₅ and R ₁₀ independently represent unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, cycloalkenyl, alkenylalkyl, alkynylalkyl, cycloalkyl Alkyl, cycloalkenylalkyl, heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl, and the heterocyclic group has 0, 1 or 2 An oxo group; the "substituted" means substituted with at least one group selected from the group consisting of an alkyl, alkenyl, alkynyl or cycloalkyl group containing no or halogen, cyano, cyanoalkyl , Halogen, mercapto, nitro, cyanothio, OR ₁₂ , -alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and alkoxyalkoxycarbonyl;

R ₄ and R ₁₁ independently represent hydrogen, unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, cycloalkenyl, alkenylalkyl, alkynylalkyl, cyclo Alkylalkyl, cycloalkenylalkyl, heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl, and the heterocyclic group has 0, 1 or 2 oxo groups; said "substituted" means substituted by at least one group selected from the group consisting of alkyl, alkenyl, alkynyl or cycloalkyl groups that do not contain or contain halogen, cyano, cyano Alkyl, halogen, mercapto, nitro, cyanothio, OR ₁₂ , -alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and alkoxyalkoxycarbonyl;

R ₁₂ and R ₁₃ independently represent hydrogen, and alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, and benzyl groups that do not contain or contain halogen;

R ₁₄ independently represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a phenyl group, and a benzyl group that do not contain or contain halogen;

m and q independently represent 0, 1 or 2, respectively, and n represents 0 or 1.

More preferably, X represents C _1-6 alkyl, C _3-6 cycloalkyl;

Y represents a hydrogen atom, a C _1-6 alkyl group that does not contain or contains halogen, a C _2-6 alkenyl group, a C _2-6 alkynyl group, an unsubstituted or C _3-6 cycloalkane substituted with a C _1-6 alkyl group base;

Z represents C _1-6 alkyl, halogen, cyano, C _1-6 alkoxy, C _1-6 alkylthio, C _1-6 alkylsulfonyl;

Q stands for

among them,

R ₁ and R ₂ independently represent hydrogen, cyano, thiocyano, cyano C _1-6 alkyl, nitro, halogen, mercapto, OR ₄ , R ₅ , SO _m -R ₅ , SO ₂ -OR ₄ , NR ₆ -SO ₂ -R ₅ , O-SO ₂ -R ₅ , NR ₆ -(C=O)-R ₄ , NR ₆ -(C=O)-OR ₄ , -(C=O)- NR ₆ -OR ₄ , NR ₇ R ₈ , SO ₂ -NR ₇ R ₈ , -(C=O)-NR ₇ R ₈ , O-(C=O)-OR ₄ , NR ₆ -(C=O) -NR ₇ R ₈ , O-(C=O)-NR ₇ R ₈ , -C _1-6 alkyl-NR ₆ -(C=O)-R ₄ , -C _1-6 alkyl-SO _2- OR ₄ , -C _1-6 alkyl -NR ₆ -SO ₂ -R ₅ , -C _1-6 alkyl -O-SO ₂ -R ₅ , -C _1-6 alkyl -SO ₂ -NR ₇ R ₈ , SO ₂ -NR ₇ -C _1-6 alkyl-S(O) _n -R ₅ , -C _1-6 alkyl-OR ₄ , (C=O)-R ₄ , (C=O)- OR ₄ , O-(C=O)-R ₄ , -C _1-6 alkyl-(C=O)-R ₄ , -C _1-6 alkyl-(C=O)-OR ₄ , -C _1-6 alkyl-O-(C=O)-R ₄ , (C=S)-R ₄ , (C=S)-OR ₄ , (C=S)-SR ₅ , (C=O)- SR ₅ , S-(C=O)-R ₄ , S-(C=S)-R ₄ , O-(C=S)-R ₄ , -C _1-6 alkyl-(C=S)- R ₄ , -C _1-6 alkyl-(C=S)-OR ₄ , -C _1-6 alkyl-(C=O)-SR ₅ , -C _1-6 alkyl-(C=S) -SR ₅ , -C _1-6 alkyl-S-(C=O)-R ₄ , -C _1-6 alkyl-O-(C=S)-R ₄ , -C _1-6 alkyl- S-(C=S)-R ₄ , -C _1-6 alkyl-SO _m -R ₅ , -OC _1-6 alkyl-NR ₇ R ₈ , -SC _1-6 alkyl-NR ₇ R ₈ , -C _1-6 alkyl-OC _1-6 alkyl-NR ₇ R ₈ , -C _1-6 alkyl-SC _1-6 alkyl-NR ₇ R ₈ , -C _1-6 alkyl-( C=O) _n -NR ₇ R ₈ , -C _1-6 alkyl-(C=S) _n -NR ₇ R ₈ , -NH-C _1-6 alkyl-NR ₇ R ₈ , P(O) (OR ₉ ) ₂ , CH ₂ P(O)(OR ₉ ) ₂ ;

R ₃ , R ₆ , R ₇ and R ₈ independently represent hydrogen, amino, nitro, cyano, mercapto, halogen, C _1-6 alkylamino, di C _1-6 alkylamino, OR ₁₁ ,- C _1-6 alkyl-OR ₁₁ , SO _q -R ₁₀ , -C _1-6 alkyl-SO _q -R ₁₀ , (C=O)-R ₁₁ , (C=O)-OR ₁₁ , R ₁₀ , C _1-6 alkylthio, C _1-6 alkylaminocarbonyl, C _1-6 alkylcarbonyl C _1-6 alkyl, C _1-6 alkoxycarbonyl C _1-6 alkyl, C _1-6 alkyl aminocarbonyl C _1-6 alkyl, C _1-6 alkylcarbamoyl, C _1-6 alkoxy, aminocarbonyl group, acyloxy C _1-6 alkyl, C _1-6 alkylthiocarbonyl, tris C _1-6 alkylsilyl, di C _1-6 alkylphosphono; or R ₇ R ₈ N- represents a six-membered heterocyclic group

R ₉ independently represents C _1-6 alkyl;

R ₅ and R ₁₀ independently represent unsubstituted or substituted C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, C _1-6 alkoxy C _1-6 alkyl, C _3-6 cycloalkenyl, C _2-6 alkenyl C _1-6 alkyl, C _2-6 alkynyl C _1-6 alkyl, C _3-6 cycloalkyl C _{1 -6} alkyl, C _3-6 cycloalkenyl C _1-6 alkyl, heterocyclyl, aryl, heteroaryl, heterocyclyl C _1-6 alkyl, aryl C _1-6 alkyl, hetero Aryl C _1-6 alkyl, and the heterocyclic group has 0, 1, or 2 oxo groups; the "substituted" means substituted by at least one group selected from: free or containing Halogen C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl or C _3-6 cycloalkyl, cyano, cyano C _1-6 alkyl, halogen, mercapto, nitro, Cyanothio, OR ₁₂ , -C _1-6 alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and C _1-6 alkoxy C _1-6 alkoxycarbonyl;

R ₄ and R ₁₁ independently represent hydrogen, unsubstituted or substituted C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, C _1-6 alkyl Oxygen C _1-6 alkyl, C _3-6 cycloalkenyl, C _2-6 alkenyl C _1-6 alkyl, C _2-6 alkynyl C _1-6 alkyl, C _3-6 cycloalkyl C _1-6 alkyl, C _3-6 cycloalkenyl C _1-6 alkyl, heterocyclic, aryl, heteroaryl, heterocyclic C _1-6 alkyl, aryl C _1-6 alkyl , Heteroaryl C _1-6 alkyl, and the heterocyclic group has 0, 1 or 2 oxo groups; "substituted" means substituted by at least one group selected from: Or halogen-containing C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl or C _3-6 cycloalkyl, cyano, cyano C _1-6 alkyl, halogen, mercapto, nitrate Group, cyanothio group, OR ₁₂ , -C _1-6 alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and C _1-6 alkoxy C _1-6 alkoxycarbonyl;

R ₁₂ and R ₁₃ independently represent hydrogen, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, phenyl, Benzyl

R ₁₄ independently represents C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, phenyl, and benzyl, which do not contain or contain halogen;

m and q independently represent 0, 1 or 2, respectively, and n represents 0 or 1.

Further preferably, X represents C _1-6 alkyl, C _3-6 cycloalkyl;

Y represents a hydrogen atom, C _1-6 alkyl, halogenated C _1-6 alkyl, C _3-6 cycloalkyl;

Z represents C _1-6 alkyl, halogen, cyano, C _1-6 alkylsulfonyl;

Q stands for

among them,

R ₁ and R ₂ independently represent hydrogen, cyano, thiocyano, cyano C _1-2 alkyl, nitro, halogen, mercapto, OR ₄ , R ₅ , SO _m -R ₅ , SO ₂ -OR ₄ , NR ₆ -SO ₂ -R ₅ , O-SO ₂ -R ₅ , NR ₆ -(C=O)-R ₄ , NR ₆ -(C=O)-OR ₄ , -(C=O)- NR ₆ -OR ₄ , NR ₇ R ₈ , SO ₂ -NR ₇ R ₈ , -(C=O)-NR ₇ R ₈ , O-(C=O)-OR ₄ , NR ₆ -(C=O) -NR ₇ R ₈ , O-(C=O)-NR ₇ R ₈ , -C _1-2 alkyl -NR ₆ -(C=O)-R ₄ , -C _1-2 alkyl -SO _2- OR ₄ , -C _1-2 alkyl -NR ₆ -SO ₂ -R ₅ , -C _1-2 alkyl -O-SO ₂ -R ₅ , -C _1-2 alkyl -SO ₂ -NR ₇ R ₈ , SO ₂ -NR ₇ -C _1-2 alkyl-S(O) _n -R ₅ , -C _1-2 alkyl-OR ₄ , (C=O)-R ₄ , (C=O)- OR ₄ , O-(C=O)-R ₄ , -C _1-2 alkyl-(C=O)-R ₄ , -C _1-2 alkyl-(C=O)-OR ₄ , -C _1-2 alkyl-O-(C=O)-R ₄ , (C=S)-R ₄ , (C=S)-OR ₄ , (C=S)-SR ₅ , (C=O)- SR ₅ , S-(C=O)-R ₄ , S-(C=S)-R ₄ , O-(C=S)-R ₄ , -C _1-2 alkyl-(C=S)- R ₄ , -C _1-2 alkyl-(C=S)-OR ₄ , -C _1-2 alkyl-(C=O)-SR ₅ , -C _1-2 alkyl-(C=S) -SR ₅ , -C _1-2 alkyl-S-(C=O)-R ₄ , -C _1-2 alkyl-O-(C=S)-R ₄ , -C _1-2 alkyl- S-(C=S)-R ₄ , -C _1-2 alkyl-SO _m -R ₅ , -OC _1-2 alkyl-NR ₇ R ₈ , -SC _1-2 alkyl-NR ₇ R ₈ , -C _1-2 -OC _1-2 alkyl group -NR ₇ R _8, -C _1-2 alkyl -SC _1-2 alkyl group -NR ₇ R _8, -C _1-2 alkyl - ( C=O) _n -NR ₇ R ₈ , -C _1-2 alkyl-(C=S) _n -NR ₇ R ₈ , -NH-C _1-2 alkyl-NR ₇ R ₈ , P(O) (OR ₉ ) ₂ , CH ₂ P(O)(OR ₉ ) ₂ ;

R ₃ , R ₆ , R ₇ and R ₈ independently represent hydrogen, amino, nitro, cyano, mercapto, halogen, C _1-6 alkylamino, di C _1-6 alkylamino, OR ₁₁ ,- C _1-2 alkyl-OR ₁₁ , SO _q -R ₁₀ , -C _1-2 alkyl -SO _q -R ₁₀ , (C=O)-R ₁₁ , (C=O)-OR ₁₁ , R ₁₀ , C _1-6 alkylthio, C _1-6 alkylaminocarbonyl, C _1-6 alkylcarbonyl C _1-2 alkyl, C _1-6 alkoxycarbonyl C _1-2 alkyl, C _1-6 alkyl aminocarbonyl C _1-2 alkyl, C _1-6 alkylcarbamoyl, C _1-6 alkoxy, aminocarbonyl, C _1-6 alkyl acyloxy, C _1-6 alkylthiocarbonyl, tris C _1-6 alkylsilyl, di C _1-6 alkylphosphono; or R ₇ R ₈ N- represents a six-membered heterocyclic group

R ₉ independently represents methyl and ethyl;

R ₅ and R ₁₀ independently represent unsubstituted or substituted C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, C _1-6 alkoxy C _1-2 alkyl, C _3-6 cycloalkenyl, C _2-6 alkenyl C _1-2 alkyl, C _2-6 alkynyl C _1-2 alkyl, C _3-6 cycloalkyl C _{1 -2} alkyl, C _3-6 cycloalkenyl C _1-2 alkyl, heterocyclic, aryl, heteroaryl, heterocyclic C _1-2 alkyl, aryl C _1-2 alkyl, hetero Aryl C _1-2 alkyl, and the heterocyclic group has 0, 1 or 2 oxo groups; the "substituted" means substituted by 1 to 2 groups selected below: not included Or halogen-containing C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl or C _3-6 cycloalkyl, cyano, cyano C _1-2 alkyl, halogen, mercapto, nitrate Group, cyanothio group, OR ₁₂ , -C _1-2 alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and C _1-6 alkoxy C _1-2 alkoxycarbonyl;

R ₄ and R ₁₁ independently represent hydrogen, unsubstituted or substituted C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, C _1-6 alkyl Oxygen C _1-2 alkyl, C _3-6 cycloalkenyl, C _2-6 alkenyl C _1-2 alkyl, C _2-6 alkynyl C _1-2 alkyl, C _3-6 cycloalkyl C _1-2 alkyl, C _3-6 cycloalkenyl C _1-2 alkyl, heterocyclyl, aryl, heteroaryl, heterocyclyl C _1-2 alkyl, aryl C _1-2 alkyl , Heteroaryl C _1-2 alkyl, and the heterocyclic group has 0, 1 or 2 oxo groups; "substituted" means substituted by 1 to 2 groups selected from: C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl or C _3-6 cycloalkyl without or containing halogen, cyano, cyano C _1-2 alkyl, halogen, mercapto , Nitro, cyanothio, OR ₁₂ , -C _1-2 alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and C _1-6 alkoxy C _1-2 alkoxycarbonyl;

R ₁₂ and R ₁₃ independently represent hydrogen, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, phenyl, Benzyl

R ₁₄ independently represents C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, phenyl, and benzyl, which do not contain or contain halogen;

m and q independently represent 0, 1 or 2, respectively, and n represents 0 or 1.

Even more preferably, X represents methyl, ethyl, isopropyl, cyclopropyl;

Y represents hydrogen atom, methyl, ethyl, trifluoromethyl, cyclopropyl;

Z represents methyl, chlorine, fluorine, cyano, methylsulfonyl;

Q stands for

among them,

R ₁ and R ₂ independently represent hydrogen, C _1-6 alkyl, halogenated C _1-6 alkyl, halogen, C _3-6 cycloalkyl, C _1-6 alkoxy, halogenated C _{1- 6} alkoxy, C _1-6 alkoxycarbonyl, phenyl, pyridyl;

R ₃ represents methyl and ethyl.

The method for synthesizing 4-(3-heterocyclic-1-benzoyl)pyrazole compounds includes the following steps:

Acyl halide reaction to obtain compound III, and then esterification reaction with compound IV to prepare the compound represented by general formula I; the reaction equation is as follows:

Among them, Hal represents halogen, preferably chlorine;

The acyl halogenation reaction is carried out in the presence of a halogenating reagent and a solvent, the reaction temperature is 0-100°C, preferably, the halogenating reagent is dichlorosulfoxide, and the solvent is selected from acetonitrile, DMF, THF, methylene chloride , One or more combinations of dichloroethane; esterification reaction is carried out in the presence of a solvent and a base, the reaction temperature is 0-100 ℃, preferably, the solvent is acetonitrile, DMF, THF, methylene chloride , One or more combinations of dichloroethane, the base is triethylamine, NMM or DIPEA.

In the definition of the above compound formula, the technical terms used, whether used alone or in compound words, represent the following substituents:

Halogen: refers to fluorine, chlorine, bromine, iodine.

Alkyl: refers to straight-chain alkyl or branched-chain alkyl. For example, in the compound word "-alkyl-OR ₄ ", the alkyl group may be -CH ₂ -, -CH ₂ CH ₂ -, -CH(CH ₃ )- and so on. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl Group, tert-butyl or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, butylene -3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds can be at any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl having, for example, three to six carbocyclic members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, where the double bond can be at any position.

Haloalkyl: refers to a linear or branched alkyl group in which all or part of the hydrogen atoms are replaced by halogen atoms.

Alkoxy: refers to a functional group after an alkyl group is connected to an oxygen atom.

Unless otherwise specified, the "aryl" in the present invention includes but is not limited to phenyl, naphthyl,

The "heterocyclic group" includes but is not limited to those having 0, 1, or 2 oxo groups

The "heteroaryl" means an aromatic cyclic group containing, for example, 3 to 6 ring atoms and optionally a benzo ring, and 1 to 4 of the ring atoms (for example, 1, 2 , 3 or 4) are heteroatoms (such as oxygen, nitrogen and/or sulfur), for example

If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups which are the same or different groups selected from those mentioned. In addition, the same or different substitution characters contained in the same or different substituents are independently selected, for example, two R ₅ groups in “R ₅ ”and “SO _m -R ₅ ” are independently selected from R ₅ The same groups may be the same or different. The two R ₉ groups in “P(O)(OR ₉ ) ₂ ”are independently selected from those mentioned by R ₉ , and may be the same or different. . The same applies to ring systems formed by different atoms and units. At the same time, the scope of the claims will exclude compounds that are known to those skilled in the art to be chemically unstable under standard conditions.

In addition, unless otherwise specified, multiple parallel substituents (separated by "," or "or") in the present invention have the above-mentioned qualifiers for each subsequent substituent, such as "free or containing halogen""Alkyl, alkenyl, alkynyl or cycloalkyl" in the "free or containing halogen" has a limiting role for each subsequent group "alkyl""alkenyl""alkynyl""cycloalkyl" . Groups (including heterocyclic groups, aryl groups, etc.) that are not marked with specific connection positions can be connected at any position, including the position connected to C or N; if it is substituted, the substituent can also be substituted at any position , As long as the rules for chemical bonding are met. As heteroaryl substituted by 1 methyl

Representative

Wait.

If necessary, the pyrazole compound having the structure of formula I can form the corresponding salt by conventional methods, and the salt can be any form of salt as long as it can be used in agriculture, such as alkali metal salts (such as sodium or potassium salts) ), alkaline earth metal salts (such as magnesium or calcium salts), or ammonium salts (such as dimethylamine or triethylamine salts).

Solvates of the compounds of the invention are also included in the invention.

The compounds involved in the present invention may exist in the form of one or more stereoisomers. Various isomers include enantiomers, diastereomers, and geometric isomers. These isomers, including mixtures of these isomers, are within the scope of the present invention.

A herbicide composition comprising a herbicidally effective amount of at least one of the 4-(3-heterocyclyl-1-benzoyl)pyrazole compounds or salts thereof.

The herbicide composition also includes formulation aids.

A method for controlling weeds, which comprises weeding an effective amount of at least one of the 4-(3-heterocyclyl-1-benzoyl)pyrazole compounds or salts thereof or the weeding The agent composition is used on plants or weed areas.

The use of at least one of the 4-(3-heterocyclic-1-benzoyl)pyrazole compounds or salts thereof as described or the herbicide composition for controlling weeds, preferably, The 4-(3-heterocyclyl-1-benzoyl)pyrazole compound or its salt is used to control weeds in useful crops, which are processed by transgenic crops or genome editing technology crop.

For many economically important monocotyledonous and dicotyledonous weeds, the compounds of the formula I according to the invention have outstanding herbicidal activity. The active substances of the present invention are also effective for perennial weeds, which grow 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 germination or after germination. Particular mention is made of representative examples of monocotyledonous and dicotyledonous weed colonies that can be controlled by the compounds of the present invention, and there is no limitation to certain species. Examples of weed species where the active substance works effectively include monocotyledons: annual oats, rye, grass, hordeum, ferraris, barnyardgrass, crabgrass, foxtail and sedge, and perennial ice Grasses, bermudagrass, chrysanthemum and sorghum, and perennial sedges.

Regarding dicotyledonous weed species, the effects of which can be extended to species such as the annual Swine, Viola, Pompona, Wild Sesame, Stellaria, Amaranthus, Sphaeropsis, Ipomoea, Hirsch Genus, Matricaria and Abutilon, and perennial weeds Convolvulus, Thistle, Rumex and Artemisia. The active substance of the present invention can effectively control weeds under the conditions to be sown in rice, such as barnyardgrass, Cicu, Alisma, water chestnut, sugarcane and sedge. If the compound of the present invention is applied to the soil surface before germination, weed seedlings can be completely prevented before the weeds grow, or the weeds can stop growing when they grow cotyledons, and finally die completely after three to four weeks. The compounds of the present invention are particularly active against the following plants, Apila grass, Ono sesame, Polygonum sibiricum, Stellaria, Ivy leaf Pompa, Arab Pompa, Pansy and Amaranthus, Potentilla and Kochia .

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

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

The compounds of the formula I or salts thereof of the present invention are preferably used for economically important transgenic crops and ornamental plants, such as cereals, such as wheat, barley, rye, oats, millet, rice, cassava and corn, or for sugar beets, Cultivation of cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetable plants. The compounds of formula I are preferably used as herbicides for the cultivation of useful plants, which plants are resistant or resistant to the toxic effects of the herbicides through genetic engineering.

Conventional methods for breeding plants with improved shapes compared to known plants include, for example, traditional mating methods and mutant breeding. In other words, new plants with improved traits can be obtained by means of genetic engineering (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 change crop plants (eg WO 92/11376, WO 92/14827, WO 91/19806);

-Genetically modified crop plants that are resistant to specific herbicides, glufosinate (glufosinate) herbicides (eg EP-0242236A, EP-0242246A) or glyphosate herbicides (WO92/00377 ), or sulfonylurea herbicides (EP-0257993 A, US-5013659 A);

-Transgenic crop plants such as cotton, which can produce Bacillus thuringiensis toxin (Bt toxin), this toxin can protect plants against specific pests (EP-0142924A, EP-0193259A);

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

Many molecular biotechnologies that can produce transgenic plants with improved traits are known (see, for example, Sambrook et al., 1989, Molecular Amplification, Second Handbook of Experiments, Published by Cold Spring Harbor Laboratory, Cold Spring Harbor, New York; or Winnacker "Gene Kunde "[Genes and Cloning], 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 DNA sequences. Using the standard methods described above, for example, it is possible to exchange substrates, remove partial sequences, or add natural or synthetic sequences. In order to connect DNA fragments to each other, it is possible to attach binders or linkers to the fragments.

Plant cells with reduced activity gene products can be prepared by the following methods, 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 above-mentioned 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 DNA molecules that contain only a portion of the coding sequence, which must be long enough to achieve 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 completely identical.

When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired plant cell compartment. However, in order to locate in a specific chamber, it is possible, for example, to connect the coding region and the DNA sequence to ensure the localization at a specific position. 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 recombined into whole plants using known techniques. The transgenic plant can be any desired plant variety, namely monocotyledonous and dicotyledonous plants. In this way, it is possible to obtain transgenic plants with improved traits by overexpressing, inhibiting or inhibiting homologous (=natural) genes or gene sequences, or by expressing heterogeneous (=external) genes or gene sequences.

When using the active substance of the present invention on transgenic crops, in addition to the observable weed suppression effect on other crops, there are often special effects on the corresponding transgenic 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 effects of growth and yield of transgenic crop plants. Therefore, the present invention also provides the use of the compound as a herbicide for controlling weeds 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 directionally control plant components and promote harvesting, such as drying and dwarfing plant growth. And they are also suitable for regulating and inhibiting undesired plant growth without destroying the growth of crops. Inhibiting plant growth plays a very important role in many monocotyledonous and dicotyledonous crops, because this can reduce or completely prevent lodging.

The compound of the present invention can be applied using general preparations, and wettable powders, concentrated emulsions, sprayable solutions, powders or granules can be used. Thus the present invention also provides herbicide compositions comprising compounds of formula I. The compound of formula I can be formulated in a variety of ways according to 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 solution, suspension concentrate (SC), dispersible oil suspension (OD), suspension with oil or water as diluent, solution of miscible oil, powder (DP), capsule suspension (CS ), seeddressing composition, particles for spreading and soil application, spraying particles, coating particles and absorbing particles, water-dispersible particles (WG), water-soluble particles (SG), ULV (super Low volume) formulas, microcapsules and wax products. These individual formulation types are known and are described in documents such as Winnacker-Küchler, "Chemische Techonologie" [Chemical Process], Volume 7, C. Hauser Verlag Munich, 4th edition 1986; Wade Vank Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" manual, 3rd edition 1979, G. Goodwin Ltd. London.

Necessary formulation aids, such as inert substances, surfactants, solvents and other additives are also known and described in the following documents, such as Watkins'"Handbook of Powder Diluent Insecticides and Carriers", Second Edition, Darland book 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, "Surface Encyclopedia", Chemical Publishing Company, NY1964;

of

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

Wettable powders can be uniformly dispersed in water. In addition to active substances, they also include diluents or inert substances, ionic and non-ionic surfactants (wetting agents, dispersants), such as polyethoxyalkylphenols, poly Ethoxy fatty alcohol, polyoxyethyl aliphatic amine, fatty alcohol polyglycol ether sulfate, alkyl sulfonate, alkyl phenyl sulfonate, sodium lignosulfonate, 2,2'-dinaphthyl methane Sodium -6,6'-disulfonate, sodium dibutylnaphthalene sulfonate or sodium oleoyl methyl taurine. For the preparation of wettable powders, the active substances of the herbicides are finely ground, for example using commonly used equipment, such as hammer mills, fan mills and jet mills, and the adjuvants are mixed simultaneously or sequentially.

Dissolve the active substance in an organic solvent to prepare a concentrated emulsion. Solvents such as butanol, cyclohexanone, dimethylformamide, xylene, or a mixture of higher boiling aromatic compounds or hydrocarbons or solvents, and then add one One or more ionic and/or nonionic 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, alkyl aromatic polyglycol ethers, fatty alcohols Polyglycol ether, propylene oxide-ethylene oxide condensation product, alkyl polyether, sorbitan ester such as sorbitan fatty acid ester, or polyoxyethylene sorbitan such as polyoxyethylene sorbitan fatty acid ester Polysaccharide ester.

The active substance and finely divided solid substance are ground to obtain a powder, such as talc, natural clay such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. The suspension based on water or oil can be prepared by, for example, wet grinding using a commercially available glass bead mill, with or without the addition of a surfactant of the other formulation type described above.

To prepare an emulsion such as an oil-in-water emulsifier (EW), an organic solvent containing water can be used, a stirrer, a colloid grinder, and/or a static mixer, and if necessary, a surfactant of another formulation type as described above is added.

Use the following method to prepare granules, spray the active material onto the adsorbate, granulate with inert materials, or concentrate the active material onto the surface of a carrier such as sand or kaolinite, granulate the inert materials through a binder, and stick Mixtures such as polyvinyl alcohol, sodium polyacrylate or mineral oil. The method of preparing fertilizer granules can be used to pelletize suitable active substances, and fertilizers can be mixed if necessary. Aqueous granules are prepared using conventional methods, such as spray-drying, fluidized bed granulation, milling disk granulation, mixing using a high-speed mixer, and extruding without solid inert materials.

For the preparation methods using grinding discs, fluidized beds, extruders and spray granules, see the following processes, such as "Spray Drying Manual" Third Edition 1979, G. Goodwin Ltd., London; JEBrowning, "Agglomeration", Chemistry and Engineering 1967, p. 147ff; "Perry's Chemistry Engineer's Handbook", Fifth Edition, McGraw-Hill, New York 1973, p. 8-57. If you want to know about the formulation of crop protection products, see, for example, GCKlingman, “Weed Controls as Science”, John Wiley and Sons, New York, pp. 81-96, 1961 and JDFreyer, SAEvans “Weed Control Manual”, Fifth Edition, Blackwell Scientific Rubblications, Oxford University 1968, pages 101-103.

Agrochemical formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% of 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%. Powder formulations contain 1 to 30% by weight of active substance, usually preferably 5 to 20% by weight of active substance, whereas sprayable solutions contain about 0.05 to 80% by weight, preferably 2 to 50% of active substance . Regarding the content of the active substance in the water-suspended granules, it mainly depends on whether the active substance is liquid or solid, and the additives, fillers, etc. 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 formulation of the active substance may include a tackifier, wetting agent, dispersant, emulsifier, penetrant, preservative, antifreeze, solvent, filler, carrier, colorant, defoamer, evaporation inhibitor and PH and viscosity modifiers are commonly used in all cases.

Based on these preparations, it may also be mixed with other insecticide active substances such as insecticides, acaricides, herbicides and fungicides, and may also be mixed with safeners, fertilizers and/or plant growth regulators, the mixing method may be For pre-mixing or filling and mixing.

In a compound preparation or a tank-mix preparation, suitable active substances that can be mixed with the active substances of the present invention are, for example, "World Pesticide New Variety Technology Encyclopedia", China Agricultural Science and Technology Press, 2010.9 and the documents cited here. Known substances. For example, the herbicide active substances mentioned below can be mixed with the 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, where appropriate, code): acetochlor Amine, butachlor, alachlor, propachlor, metolachlor, sinoprofen, alachlor, alachlor, toxachlor, cyproteron, naproxen, R-levonal Alachlor, Dipropanil, fenclofen, difenochlor, fenfluramide, alafenamide, flufenacetamide, bromobutanil, dimethyl thiazopyr, high-efficiency dimethyl Tetrachlor, ethoxyfen, chlorfenapyr, tetromethoxam, metazachlor, clomazone, high-efficiency methyl strawgrass, high-efficiency propylpropoxylate, dimethochlor, dimethoprim , Butachlor, cyproteron, flufenachlor, heptachlor, isobutachlor, propachlor, terbutachlor, xylolachlor, dimethylchlor, alachlor, Trimechlor, chloroformamide, cyproteron, valerox, chloramphenicol, neoyanlin, tricyclachlor, butenochlor, forage, benzalkonium, quinone Phenylamine, fenfluramide, naproxen, acetochlor, naphthachlor, chlorfenapyr, pymetrozine, benomyd, oxamethoxazole, chlorophthalimide, butamidide, fluroxypyr Amine, atrazine, simazine, promethazine, cyanochlor, acetochlor, atrazine, promethazine, isopropyl, fluroxypyr, terbutaline, terbutazone, triazine fluoxamol , Ciprofloxacin, Gampuzin, Caodajin, Promethazine, Cimaton, Azidene, Diquat, Isoprolate, Ciprofloxacin, Methazone, Another Dingjin, Zhongdingtong, Special Ding Tong, Methoxypropyl, Cyanoxystrobin, Imazuron, Clotin, Atrazine, Methon, Glycyrazine, Cyanuric Acid, Indaziflam, Lursulfuron, Metsulfuron, Bensulfuron, Chlorine Pysulfuron-methyl, besulfuron-methyl, thisulfuron-methyl, pyrisulfuron-methyl, methyldisulfuron-methyl, methyl iodosulfuron-methyl sodium salt, formamidosulfuron-methyl, ethersulfuron-methyl, ethersulfuron-methyl, sulfometuron-methyl Chlorsulfuron, nicosulfuron, trisulfuron, acrimsulfuron, ethoxysulfuron, cyprosulfuron, sulfasulfuron, tetrazosulfuron, pyrimsulfuron, monosulfuron, Monosulfuron, fluorosulfuron, fluoropyrsulfuron, fluoropyrsulfuron, epoxypyrsulfuron, oxasulfuron, fluorosulfuron, profensulfuron, trifluorosulfuron, Sulsulfuron-methyl, trifluorosulfuron-methyl, flusulfuron-methyl, trifluoromethyl-sulfuron-methyl, metsulfuron-methyl sodium salt, flufensulfuron-methyl, sulfasulfuron-methyl, pyrisulfuron-methyl, propyrisulfuron Long), azimesulfuron, triflufenazone, fluoxafen, milflurazine, acetoflufen, acetoflufen, ethoxyfop-methyl, gluconate, befenazone, chlorflufen Ethyl acetate, mecarboxyl ether, triflufon-methyl, methoxytrimfon, triflufoxyn, fluorinated herbicidal ether, fluroxypyr, herbicidal ether, acetochlor, dimethoate, fluoroester oxime Glufosinate, fluroxypyr, Halosafen, chlormeron, isoproturon, rifauron, diuron, sapron, fluroxon, phendiuron, metsulfuron, bensulfuron, sulfathion Long, Isoxuron, Tebusulfuron, Ethylsulfuron, Chlorosulfuron, Methylsulfuron, Fensulfuron, Metochlor, Bromulon, Methonon, Green Valley Long, Huancaolong, Fecaolong, Fluorine Thiuron, chlorpyrifos, cyperuron, chlorpyrrolone, isopyrrolone, cyclosulfuron, thifluron, thidiazuron, veluron, p-fluorofuran, methamthiazolon, carbosulfur, trimethoprim, Oxazolon, Monisouron, Anisuron, Methiuron, Chloreturon, Teflon, Betaine, Betaine-ethyl ester, Betaine, Sulforazone, Teclofen, Oatrol, Anilin, Chloramphenicol, Diclofenac Ester, chlorpyrifos, chlorpyral, carboxazole, Chlorprocarb, Fenasulam, BCPC, CPPC, Carbasulam, butachlor, chlorpyrifos, chlorpyrifos, chlorpyrifos, dicamba, piperazine, dicamba, barnyardgrass Caodan, Huancaodi, Oatmeal, Bentachlor, Ethiopyr, Pingcaodan, Kecaomeng, Bencaodan, Zhongcaodan, Thiamethoxam, Camazon, Isopolinate, Methiobencarb, 2, 4-drop butyl ester, 2 methyl 4 sodium chloride, 2,4-D isooctyl ester, 2 methyl 4 chloro isooctyl ester, 2,4-D sodium salt, 2,4-D dimethylamine salt, 2 A 4 Ethyl chloride, 2 methyl 4 chloro, 2,4-D propionic acid, high 2,4-D propionate, 2,4-D butyric acid, 2 methyl 4 chloropropionic acid, 2 methyl 4 chloropropionate , 2 methyl 4-chlorobutyric acid, 2,4,5-dipyrane, 2,4,5-dipropionic acid, 2,4,5-dibutyric acid, 2 methyl-4 chloramine salt, dicamba, chlorfenapyr, Valerac, saison, triclosan, trichlorobenzoic acid, trimethoprim, chlorpyrifos, diflufenicol, diflufenicol, diflufenar, diflufenicol, high-efficiency pyrimidine Fluclomethoxazole, quizalofop, quizalofop, oxaconazole, oxamethoxazole, oxaprofen, cyflufenazone, oxachlor, cyprodin, thiazolacarb , Cypromethrin, oxypentalin, triflufenazone oxime, clomazone, paraquat, diquat, acesulfame, ethamfluran, isoprofen, mesotrimethrin, ciprofloxacin Fipron, Amifoprin, Ethflurane, Chlorfenflur, Amethoprim, Difluralin, Chlorethdifloxacin, Methalpropalin, Propofol, Glyphosate, Sarcofosine, Glufosinate , Methylamine glufosinate, glufosinate, glufosinate, bisphosphinate, diphosphazin, glufosinate, glufosinate, valerosin, dimeglufosin, glufosinate, imidazole nicotinic acid, imidazole nicotinic acid , Imidazoquinolinic acid, methoxamethoxam, methoxazone ammonium salt, methoxazole nicotinic acid, imazamate, chlorofluoropyroxyacetic acid, chlorofluoropyroxyacetic acid isooctyl ester, diclofenac, ammonia Clopyralid, triclofenac, fluroxypyr, fluroxypyr, triclofenol, thiacloprid, fluroxypyr, clopyralid, fluroxypyr, triclofenac butoxy Ethyl ethyl ester, Cliodinate, diclofenac, clethodim, chlorfenapyr, chlorfenapyr, ciclofenone, bufofenone, oxadiazon, pyranone, buthidazole, imazalone, cycloazinone , Fenoxazone, acetochlor, Ametridione, Amibuzin, bromoxynil, octanoyl bromoxynil, octanoyl iodobenzonitrile, iodobenzonitrile, diquat, diphenylacetonitrile, bisacrylonitrile, hydroxydimethy Oxynitrile, Iodobonil, azole Sulfamethoxam, alafenamide, penoxsulam, sulfoxazosin, chlorfenazone, alafenamide, alafenamide, fluoxaron, dimefen, pyrimethanil Ethers, cyclic esters of glufosinate, pyraclostrobin, azoxystrobin, dicyclosulone, mesotrione, sulcotrione, Tembotrione, Tefuryltrione, Bicyclopyrone, Ketodpiradox, isoxachlor, clomazone, Fenoxasulfone, Methiozolin, Ipramethoprim, Mepyrazine, Pyrazolate, Wild Paraquat, Benzoconazole, Metazarone, Pyclofen, Pyrasulfotole, Oxachlor, Pyroxasulfone, Pyraclostrobin Oxaconazole, trimethoprim, chlorfenapyr, chlorpyrifosin, fluoxazone, mesotrione, Bencarbazone, fenflurazine, flufenazone, herbicide, clomazone, clomazone Pyridinium, Tetradinium, Flupropacil, Indoxachlor, Flufenoxalic Acid, Propyrhyflur, Mepyramine, Phthalate, Flumezin, Pentachlorophenol (Sodium), Dylenol, Tetral, Tetral Oxalate, pentolphenol, dinitrophenol, chlorophenol, diloxate, diloxate, propynyl oxadiazone, oxadiazone, cyclopentazone, fluoxazone, methyl oxalate, tetramethoate Oxachlor, flupyrazine, chlorfenapyr, bromochlor, dimethal, fenpyr, pyridoxine, pyridone, chlorpyrifos, dalpyrifos, pyridafol, quinclorac, chlormethalin Quinolinic acid, bendazon, dapyrazine, oxadiazon, chlorpyrifos, clomazone, cycloheptafen, isopropyl chlorfen, propyl fenpyr, indoxazone, sodium chlorate, Thatch, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, forage fast, bromophenol oxime, triazole sulfonate, trimethoxazole, furoxazone, furosemide, acetosulfur, pyrimethanil Amine, chlorophthalic acid, fluroxypyr, barnyard grass dilute, acrolein, benzeben, chlorfenapyr, oat ester, thiadiazolamide, trimethoprim, hypromone, methoxybenzone, benzoin Sulfachlor, chlorfenapyr, trichloropropionic acid, Alorac, Diethamquat, Etnipromid, Iprymidam, Ipfencarbazone, Thiencarbazone-methyl, Pyrimisulfan, Chlorflurazole, Tripropindan, Sulglycapin, sulfamethoxazole, Cambendichlor, cyprodinil, thiocyanate Aniline, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, acetonitrile, oxazane, oxazalil, oxazin, pyrazolin, pyrazolin, Oximepyral, bisoxazolic acid, dichloropropenylamine, fluorochloropyridine ester, DOW chlorofluoropyridine 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, if necessary, the commercially available formulations are diluted in a usual manner, for example, in the case of wettable powders, concentrated emulsions, suspensions, and particles suspended in water, diluted with water. Powders, granules for soil application, or solutions for spreading and spraying generally do not need to be further diluted 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 so on. It can have a large variation range, 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

In view of the economics, diversity and biological activity of the compounds, we have preferably synthesized some compounds. Among the many compounds synthesized, selected parts are listed in the following table. The specific compound structure and corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better description of the present invention, but do not limit the present invention. Those skilled in the art should not understand this as the scope of the above subject of the present invention is limited to the following compounds.

Table 1 Compound structure and its ¹ H NMR data

The above-mentioned contents of the present invention will be further described in detail through the specific embodiments provided in the following examples. Those skilled in the art should not understand this as the scope of the above-mentioned subject matter of the present invention is limited to the following examples; The technologies implemented in the above-mentioned contents of the present invention belong to the scope of the present invention. The process parameters and product yields in the following examples are not optimized.

Examples of representative compounds are as follows. The synthesis methods of other compounds are similar and will not be described in detail here.

1. Synthesis of Compound 1

Put pyrazolic acid (1.05eq), dichloroethane (50ml), DMF (3 drops), add dichlorosulfoxide (1.5eq) dropwise at 65°C, drop and stir for 1h without any remaining pyrazolic acid, half off Dichloroethane, standby (cool down to 55 degrees); put a (1g), dichloroethane (50ml), triethylamine (1.05eq) in another reaction bottle, cool to 15 degrees, add 55 degrees dropwise to keep warm The pyrazolic acid chloride was dripped at 15°C for 1h, and the reaction was completed. The water was added to adjust the pH to about 3, and the temperature was raised to 50°C for 0.5h. The organic layer was separated and washed again with water. After removing the solvent, it was beaten and dried with ethanol The product 1 was dried in 80% yield.

2. Synthesis of Compound 10

Put b (1g), dichloroethane (50ml), cool to 20 degrees, add a few drops of DMF to catalyze, add oxalyl chloride (1.1eq) dropwise, control the temperature at 20 degrees, after the dropwise addition, stir for 1h, and control to b Less than 1%, the reaction is completed to obtain c dichloroethane solution and directly go to the next step;

Add dichloroethane (50ml), sodium carbonate (1.2eq), water (50ml), pyrazolol (1.05eq), drop the temperature below 10 degrees, add the c dichloroethane solution obtained in one step at 10 degrees, drop After adding heat for 1h, warming to 50°C for 1h, heat-separating, taking the organic layer and washing with twice the mass of cold water once, separating the organic layer; the organic layer is refluxed with water to remove moisture, and the temperature is reduced to 30°C. Triethylamine (10ml) and acetone cyanohydrin (1ml), heated to 50 degrees for two hours, the raw material c in the control is less than 1%. Reduce the temperature to less than 10 degrees, adjust the pH to about 2 with hydrochloric acid, and separate the liquid to obtain an organic layer. After washing again with water, remove half of the solvent. The solid is precipitated by cooling and filtered to obtain e.

Put pyrazolic acid (1.05eq), dichloroethane (50ml), DMF (3 drops), add dichlorosulfoxide (1.5eq) dropwise at 60 degrees Dichloroethane, standby (cool down to 50 degrees); put e (1eq), dichloroethane (50ml), triethylamine (1.05eq) into another reaction bottle, cool to 10 degrees, add 50 degrees dropwise to keep warm The pyrazolic acid chloride was dripped at 10°C for 1h. After the reaction was controlled, water was added to adjust pH=3, and the temperature was raised to 50°C for 0.5h. The organic layer was separated and washed again with water. After the solvent was removed, it was beaten with ethanol. After drying, the product 10 is obtained with a total yield of 65%.

3. Synthesis of Compound 103

Put pyrazolic acid (1.05eq), dichloroethane (50ml), DMF (3 drops), add dichlorosulfoxide (1.5eq) dropwise at 60 degrees Dichloroethane, standby (cool down to 60 degrees); put a (1g), dichloroethane (50ml), triethylamine (1.05eq) in another reaction bottle, cool down to 20 degrees, add 60 degrees to keep warm Pyrazolic acid chloride, after the drop of 10 degrees, the reaction was completed for 1h, the reaction was completed, the water was added to adjust the pH = 3, the temperature was raised to 50 degrees for 0.5h, the organic layer was separated and washed again with water, after removing the solvent, it was beaten with ethanol The product 103 was dried in 85% yield.

4. Synthesis of compound 141

Put pyrazolic acid (1.05eq), dichloroethane (50ml), DMF (3 drops), add dichlorosulfoxide (1.5eq) dropwise at 70 degrees Dichloroethane, standby (cool down to 50 degrees); put a (1g), dichloroethane (50ml), triethylamine (1.05eq) in another reaction bottle, cool down to 10 degrees, add 50 degrees dropwise to keep warm Pyrazolic acid chloride, after dripping at 20°C for 1h, the control reaction is completed, add water to adjust pH=3, warm up to 50°C for 0.5h, separate the organic layer and wash again with water. After removing the solvent, use ethanol to pulp and bake The product 141 was obtained in 82% yield.

Evaluation of biological activity:

The standard of activity level of weed destruction (ie growth control rate) is as follows:

Level 5: The growth control rate is above 85%;

Level 4: The growth control rate is greater than or equal to 60% and less than 85%;

Level 3: Growth control rate is greater than or equal to 40% and less than 60%;

Level 2: The growth control rate is greater than or equal to 20% and less than 40%;

Level 1: The growth control rate is greater than or equal to 5% and less than 20%;

Level 0: The growth control rate is less than 5%.

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

Post-emergence test experiment: Place monocotyledonous and dicotyledonous weed seeds and main crop seeds (wheat, corn, rice, soybean, cotton, rape, millet, sorghum) in a plastic pot filled with soil, and then cover 0.5-2 Centimeters of soil to grow in a good greenhouse environment, treat the test plants at the 2-3 leaf stage after sowing for 2-3 weeks, dissolve the compound of the invention to be tested with acetone, then add Tween 80, use a certain Dilute water to a solution with a certain concentration and spray it on the plants with a spray tower. After application, the plants were cultivated in the greenhouse for 3 weeks. After 3 weeks, the experimental effects of weeds are shown in Table 2.

Table 2. Post-emergence weed experiments

Compound number	Barnyard grass	Matang	Green bristlegrass	Goosegrass	corn	wheat
1	5	5	5	5	0	0
2	5	5	5	5	0	0
3	5	5	5	5	0	0
5	5	5	5	5	0	0
7	5	5	5	5	0	0
8	5	5	5	5	0	0
10	5	5	5	5	0	0
14	5	5	5	5	0	0
16	5	5	5	5	0	0
17	5	5	5	5	0	0
18	5	5	5	5	0	0
19	5	5	5	5	0	0
20	5	5	5	5	0	0
twenty three	5	5	5	5	0	0
twenty four	5	5	5	5	0	0
28	5	5	5	5	0	0
46	5	5	5	5	0	0
72	5	5	5	5	0	0
73	5	5	5	5	0	0
76	5	5	5	5	0	0
90	5	5	5	5	0	0
98	5	5	5	5	0	0
103	5	5	5	5	0	0
104	5	5	5	5	0	0
112	5	5	5	5	0	0
123	5	5	5	5	0	0

130	5	5	5	5	0	0
141	5	5	5	5	0	0
142	5	5	5	5	0	0
143	5	5	5	5	0	0
158	5	5	5	5	0	0
167	5	5	5	5	0	0
175	5	5	5	5	0	0
Control Compound A	3	3	4	3	0	0
Control Compound B	3	3	4	3	0	0

Note: The application dose is 5 g/ha.

Control Compound A:

Control Compound B: Oxachlor.

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, respectively. The compound of the present invention to be tested was dissolved in acetone, then Tween 80 was added, diluted with a certain amount of water to a solution of a certain concentration, and sprayed immediately after sowing. After applying the medicine, it was cultivated in the greenhouse for 4 weeks. After 3 weeks, the experimental results were observed, and it was found that most of the medicament of the present invention had an excellent effect under the measurement of 250 g/ha, especially for weeds such as barnyard grass, horse tang, velvetleaf, etc. Many compounds have good selectivity to corn, wheat, rice, soybean, and rape.

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

After filling the paddy field soil in 1/1,000,000 hectares of pots, sow the seeds of barnyard grass, wolfgrass, wild Cigu, and rhododendron, etc., and gently cover the soil with it. After that, it was placed in a greenhouse with a water storage depth of 0.5-1 cm, and the tubers of Yecigu were implanted the next day or 2 days later. Afterwards, the water storage depth is 3-4 cm. When the barnyard grass, Coptis chinensis, and Agrithoprus reach 0.5 leaves, and the wild Cigu reaches the primary leaf stage, the compound of the present invention will be prepared according to the usual preparation method Aqueous dilutions of wet powders or suspending agents are uniformly dropped with a pipette to achieve the specified amount of active ingredients.

In addition, after filling a paddy field soil in a 1/1,000,000 hectare pot, it was leveled so that the water storage depth was 3-4 cm, and rice (Japonica) at the 3-leaf stage was transplanted at a transplant depth of 3 cm the next day. On the fifth day after transplantation, the compound of the present invention was treated in the same manner as described above.

The fertility status of barnyard grass, wild Cigu, Wolfgrass, and Agrithoprum was observed with the naked eye on the 14th day after drug treatment, respectively, and the herbicidal effect was evaluated at the above activity standard level of 1-5, and the results in Table 3 were obtained.

Table 3. Test activity test results (15 g/ha active ingredient)

Compound number	Barnyard grass	Ye Cigu	Wolf	Zantedeschia
1	5	4	5	5
3	5	4	5	5
5	5	4	5	5
7	5	4	5	5
14	5	4	5	5

Note: Barnyardgrass, Yecigu, Wolfgrass, and Agriganthus seeds are all collected from Heilongjiang and Jiangsu, China, and have been tested to be resistant to conventional dosages of pyrasulfuron-methyl.

At the same time, after many tests, it has been found that many of the compounds and compositions of the present invention have good selectivity to grass grasses such as Zoysia japonica, bermudagrass, tall fescue, bluegrass, ryegrass, seashore paspalum, and can be controlled Many key grass weeds and broad-leaved weeds. Tests on wheat, corn, rice, sugar cane, soybean, cotton, oil sunflower, potato, fruit tree, vegetable, etc. under different application methods also showed excellent selectivity and commercial value.

Claims (10)

1. A 4-(3-heterocyclyl-1-benzoyl)pyrazole compound or its salt having the structure of formula I:

   

   among them,

   X represents alkyl, cycloalkyl;

   Y represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an unsubstituted or alkyl-substituted cycloalkyl group that does not contain or contains a halogen;

   Z represents alkyl, halogen, cyano, alkoxy, alkylthio, alkylsulfonyl;

   Q represents unsubstituted or substituted pyrazolyl.
2. The 4-(3-heterocyclic-1-benzoyl)pyrazole compound or its salt according to claim 1, characterized in that:

   X represents C _1-8 alkyl, C _3-8 cycloalkyl;

   Y represents a hydrogen atom, a C _1-8 alkyl group containing no or halogen, a C _2-8 alkenyl group, a C _2-8 alkynyl group, an unsubstituted C _3-8 cycloalkane substituted with a C _1-8 alkyl group base;

   Z represents C _1-8 alkyl, halogen, cyano, C _1-8 alkoxy, C _1-8 alkylthio, C _1-8 alkylsulfonyl;

   Q stands for

   

   among them,

   R ₁ and R ₂ independently represent hydrogen, cyano, thiocyano, cyanoalkyl, nitro, halogen, mercapto, OR ₄ , R ₅ , SO _m -R ₅ , SO ₂ -OR ₄ , NR ₆ -SO ₂ -R ₅ , O-SO ₂ -R ₅ , NR ₆ -(C=O)-R ₄ , NR ₆ -(C=O)-OR ₄ , -(C=O)-NR ₆ -OR ₄ , NR ₇ R ₈ , SO ₂ -NR ₇ R ₈ , -(C=O)-NR ₇ R ₈ , O-(C=O)-OR ₄ , NR ₆ -(C=O)-NR ₇ R ₈ , O-(C=O)-NR ₇ R ₈ , -alkyl-NR ₆ -(C=O)-R ₄ , -alkyl-SO ₂ -OR ₄ , -alkyl-NR ₆ -SO ₂ -R ₅ , -alkyl-O-SO ₂ -R ₅ , -alkyl-SO ₂ -NR ₇ R ₈ , SO ₂ -NR ₇ -alkyl-S(O) _n -R ₅ , -alkyl- _{OR 4, (C = O)} -R 4, (C = O) -OR 4, O- (C = O) -R 4, - alkyl _{- (C = O) -R 4} , - alkyl - ( C=O)-OR ₄ , -alkyl-O-(C=O)-R ₄ , (C=S)-R ₄ , (C=S)-OR ₄ , (C=S)-SR ₅ , (C=O)-SR ₅ , S-(C=O)-R ₄ , S-(C=S)-R ₄ , O-(C=S)-R ₄ , -alkyl-(C=S )-R ₄ ,-alkyl-(C=S)-OR ₄ ,-alkyl-(C=O)-SR ₅ ,-alkyl-(C=S)-SR ₅ ,-alkyl-S- (C=O)-R ₄ ,-alkyl-O-(C=S)-R ₄ ,-alkyl-S-(C=S)-R ₄ ,-alkyl-SO _m -R ₅ ,- O-alkyl-NR ₇ R ₈ , -S-alkyl-NR ₇ R ₈ , -alkyl-O-alkyl-NR ₇ R ₈ , -alkyl-S-alkyl-NR ₇ R ₈ ,- Alkyl-(C=O) _n -NR ₇ R ₈ , -alkyl-(C=S) _n -NR ₇ R ₈ , -NH-alkyl-NR ₇ R ₈ , P(O)(OR ₉ ) ₂ , CH ₂ P(O)(OR ₉ ) ₂ ;

   R ₃ , R ₆ , R ₇ and R ₈ independently represent hydrogen, amino, nitro, cyano, mercapto, halogen, alkylamino, dialkylamino, OR ₁₁ , -alkyl-OR ₁₁ , SO _q -R ₁₀ , -alkyl-SO _q -R ₁₀ , (C=O)-R ₁₁ , (C=O)-OR ₁₁ , R ₁₀ , alkylthio, alkylaminocarbonyl, alkylcarbonylalkyl, alkyl Oxycarbonylalkyl, alkylaminocarbonylalkyl, alkylcarbamoyl, alkoxyaminocarbonyl, alkylacyloxy, alkylthiocarbonyl, trialkylsilyl, dialkylphosphono; or R ₇ R ₈ N- represents a six-membered heterocyclic group

   

   R ₉ independently represents alkyl;

   R ₅ and R ₁₀ independently represent unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, cycloalkenyl, alkenylalkyl, alkynylalkyl, cycloalkyl Alkyl, cycloalkenylalkyl, heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl, and the heterocyclic group has 0, 1 or 2 An oxo group; the "substituted" means substituted with at least one group selected from the group consisting of an alkyl, alkenyl, alkynyl or cycloalkyl group containing no or halogen, cyano, cyanoalkyl , Halogen, mercapto, nitro, cyanothio, OR ₁₂ , -alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and alkoxyalkoxycarbonyl;

   R ₄ and R ₁₁ independently represent hydrogen, unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, cycloalkenyl, alkenylalkyl, alkynylalkyl, cyclo Alkylalkyl, cycloalkenylalkyl, heterocyclyl, aryl, heteroaryl, heterocyclylalkyl, arylalkyl, heteroarylalkyl, and the heterocyclic group has 0, 1 or 2 oxo groups; said "substituted" means substituted by at least one group selected from the group consisting of alkyl, alkenyl, alkynyl or cycloalkyl groups that do not contain or contain halogen, cyano, cyano Alkyl, halogen, mercapto, nitro, cyanothio, OR ₁₂ , -alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and alkoxyalkoxycarbonyl;

   R ₁₂ and R ₁₃ independently represent hydrogen, and alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, and benzyl groups that do not contain or contain halogen;

   R ₁₄ independently represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a phenyl group, and a benzyl group that do not contain or contain halogen;

   m and q independently represent 0, 1 or 2, respectively, and n represents 0 or 1.
3. The 4-(3-heterocyclic-1-benzoyl)pyrazole compound or its salt according to claim 1, characterized in that:

   X represents C _1-6 alkyl, C _3-6 cycloalkyl;

   Y represents a hydrogen atom, a C _1-6 alkyl group that does not contain or contains halogen, a C _2-6 alkenyl group, a C _2-6 alkynyl group, an unsubstituted or C _3-6 cycloalkane substituted with a C _1-6 alkyl group base;

   Z represents C _1-6 alkyl, halogen, cyano, C _1-6 alkoxy, C _1-6 alkylthio, C _1-6 alkylsulfonyl;

   Q stands for

   

   among them,

   R ₁ and R ₂ independently represent hydrogen, cyano, thiocyano, cyano C _1-6 alkyl, nitro, halogen, mercapto, OR ₄ , R ₅ , SO _m -R ₅ , SO ₂ -OR ₄ , NR ₆ -SO ₂ -R ₅ , O-SO ₂ -R ₅ , NR ₆ -(C=O)-R ₄ , NR ₆ -(C=O)-OR ₄ , -(C=O)- NR ₆ -OR ₄ , NR ₇ R ₈ , SO ₂ -NR ₇ R ₈ , -(C=O)-NR ₇ R ₈ , O-(C=O)-OR ₄ , NR ₆ -(C=O) -NR ₇ R ₈ , O-(C=O)-NR ₇ R ₈ , -C _1-6 alkyl-NR ₆ -(C=O)-R ₄ , -C _1-6 alkyl-SO _2- OR ₄ , -C _1-6 alkyl -NR ₆ -SO ₂ -R ₅ , -C _1-6 alkyl -O-SO ₂ -R ₅ , -C _1-6 alkyl -SO ₂ -NR ₇ R ₈ , SO ₂ -NR ₇ -C _1-6 alkyl-S(O) _n -R ₅ , -C _1-6 alkyl-OR ₄ , (C=O)-R ₄ , (C=O)- OR ₄ , O-(C=O)-R ₄ , -C _1-6 alkyl-(C=O)-R ₄ , -C _1-6 alkyl-(C=O)-OR ₄ , -C _1-6 alkyl-O-(C=O)-R ₄ , (C=S)-R ₄ , (C=S)-OR ₄ , (C=S)-SR ₅ , (C=O)- SR ₅ , S-(C=O)-R ₄ , S-(C=S)-R ₄ , O-(C=S)-R ₄ , -C _1-6 alkyl-(C=S)- R ₄ , -C _1-6 alkyl-(C=S)-OR ₄ , -C _1-6 alkyl-(C=O)-SR ₅ , -C _1-6 alkyl-(C=S) -SR ₅ , -C _1-6 alkyl-S-(C=O)-R ₄ , -C _1-6 alkyl-O-(C=S)-R ₄ , -C _1-6 alkyl- S-(C=S)-R ₄ , -C _1-6 alkyl-SO _m -R ₅ , -OC _1-6 alkyl-NR ₇ R ₈ , -SC _1-6 alkyl-NR ₇ R ₈ , -C _1-6 alkyl-OC _1-6 alkyl-NR ₇ R ₈ , -C _1-6 alkyl-SC _1-6 alkyl-NR ₇ R ₈ , -C _1-6 alkyl-( C=O) _n -NR ₇ R ₈ , -C _1-6 alkyl-(C=S) _n -NR ₇ R ₈ , -NH-C _1-6 alkyl-NR ₇ R ₈ , P(O) (OR ₉ ) ₂ , CH ₂ P(O)(OR ₉ ) ₂ ;

   R ₃ , R ₆ , R ₇ and R ₈ independently represent hydrogen, amino, nitro, cyano, mercapto, halogen, C _1-6 alkylamino, di C _1-6 alkylamino, OR ₁₁ ,- C _1-6 alkyl-OR ₁₁ , SO _q -R ₁₀ , -C _1-6 alkyl-SO _q -R ₁₀ , (C=O)-R ₁₁ , (C=O)-OR ₁₁ , R ₁₀ , C _1-6 alkylthio, C _1-6 alkylaminocarbonyl, C _1-6 alkylcarbonyl C _1-6 alkyl, C _1-6 alkoxycarbonyl C _1-6 alkyl, C _1-6 alkyl aminocarbonyl C _1-6 alkyl, C _1-6 alkylcarbamoyl, C _1-6 alkoxy, aminocarbonyl group, acyloxy C _1-6 alkyl, C _1-6 alkylthiocarbonyl, tris C _1-6 alkylsilyl, di C _1-6 alkylphosphono; or R ₇ R ₈ N- represents a six-membered heterocyclic group

   

   

   R ₉ independently represents C _1-6 alkyl;

   R ₅ and R ₁₀ independently represent unsubstituted or substituted C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, C _1-6 alkoxy C _1-6 alkyl, C _3-6 cycloalkenyl, C _2-6 alkenyl C _1-6 alkyl, C _2-6 alkynyl C _1-6 alkyl, C _3-6 cycloalkyl C _{1 -6} alkyl, C _3-6 cycloalkenyl C _1-6 alkyl, heterocyclyl, aryl, heteroaryl, heterocyclyl C _1-6 alkyl, aryl C _1-6 alkyl, hetero Aryl C _1-6 alkyl, and the heterocyclic group has 0, 1, or 2 oxo groups; the "substituted" means substituted by at least one group selected from: free or containing Halogen C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl or C _3-6 cycloalkyl, cyano, cyano C _1-6 alkyl, halogen, mercapto, nitro, Cyanothio, OR ₁₂ , -C _1-6 alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and C _1-6 alkoxy C _1-6 alkoxycarbonyl;

   R ₄ and R ₁₁ independently represent hydrogen, unsubstituted or substituted C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, C _1-6 alkyl Oxygen C _1-6 alkyl, C _3-6 cycloalkenyl, C _2-6 alkenyl C _1-6 alkyl, C _2-6 alkynyl C _1-6 alkyl, C _3-6 cycloalkyl C _1-6 alkyl, C _3-6 cycloalkenyl C _1-6 alkyl, heterocyclic, aryl, heteroaryl, heterocyclic C _1-6 alkyl, aryl C _1-6 alkyl , Heteroaryl C _1-6 alkyl, and the heterocyclic group has 0, 1 or 2 oxo groups; "substituted" means substituted by at least one group selected from: Or halogen-containing C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl or C _3-6 cycloalkyl, cyano, cyano C _1-6 alkyl, halogen, mercapto, nitrate Group, cyanothio group, OR ₁₂ , -C _1-6 alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and C _1-6 alkoxy C _1-6 alkoxycarbonyl;

   R ₁₂ and R ₁₃ independently represent hydrogen, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, phenyl, Benzyl

   R ₁₄ independently represents C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, phenyl, and benzyl, which do not contain or contain halogen;

   m and q independently represent 0, 1 or 2, respectively, and n represents 0 or 1.
4. The 4-(3-heterocyclic-1-benzoyl)pyrazole compound or its salt according to claim 1, characterized in that:

   X represents C _1-6 alkyl, C _3-6 cycloalkyl;

   Y represents a hydrogen atom, C _1-6 alkyl, halogenated C _1-6 alkyl, C _3-6 cycloalkyl;

   Z represents C _1-6 alkyl, halogen, cyano, C _1-6 alkylsulfonyl;

   Q stands for

   

   among them,

   R ₁ and R ₂ independently represent hydrogen, cyano, thiocyano, cyano C _1-2 alkyl, nitro, halogen, mercapto, OR ₄ , R ₅ , SO _m -R ₅ , SO ₂ -OR ₄ , NR ₆ -SO ₂ -R ₅ , O-SO ₂ -R ₅ , NR ₆ -(C=O)-R ₄ , NR ₆ -(C=O)-OR ₄ , -(C=O)- NR ₆ -OR ₄ , NR ₇ R ₈ , SO ₂ -NR ₇ R ₈ , -(C=O)-NR ₇ R ₈ , O-(C=O)-OR ₄ , NR ₆ -(C=O) -NR ₇ R ₈ , O-(C=O)-NR ₇ R ₈ , -C _1-2 alkyl -NR ₆ -(C=O)-R ₄ , -C _1-2 alkyl -SO _2- OR ₄ , -C _1-2 alkyl -NR ₆ -SO ₂ -R ₅ , -C _1-2 alkyl -O-SO ₂ -R ₅ , -C _1-2 alkyl -SO ₂ -NR ₇ R ₈ , SO ₂ -NR ₇ -C _1-2 alkyl-S(O) _n -R ₅ , -C _1-2 alkyl-OR ₄ , (C=O)-R ₄ , (C=O)- OR ₄ , O-(C=O)-R ₄ , -C _1-2 alkyl-(C=O)-R ₄ , -C _1-2 alkyl-(C=O)-OR ₄ , -C _1-2 alkyl-O-(C=O)-R ₄ , (C=S)-R ₄ , (C=S)-OR ₄ , (C=S)-SR ₅ , (C=O)- SR ₅ , S-(C=O)-R ₄ , S-(C=S)-R ₄ , O-(C=S)-R ₄ , -C _1-2 alkyl-(C=S)- R ₄ , -C _1-2 alkyl-(C=S)-OR ₄ , -C _1-2 alkyl-(C=O)-SR ₅ , -C _1-2 alkyl-(C=S) -SR ₅ , -C _1-2 alkyl-S-(C=O)-R ₄ , -C _1-2 alkyl-O-(C=S)-R ₄ , -C _1-2 alkyl- S-(C=S)-R ₄ , -C _1-2 alkyl-SO _m -R ₅ , -OC _1-2 alkyl-NR ₇ R ₈ , -SC _1-2 alkyl-NR ₇ R ₈ , -C _1-2 -OC _1-2 alkyl group -NR ₇ R _8, -C _1-2 alkyl -SC _1-2 alkyl group -NR ₇ R _8, -C _1-2 alkyl - ( C=O) _n -NR ₇ R ₈ , -C _1-2 alkyl-(C=S) _n -NR ₇ R ₈ , -NH-C _1-2 alkyl-NR ₇ R ₈ , P(O) (OR ₉ ) ₂ , CH ₂ P(O)(OR ₉ ) ₂ ;

   R ₃ , R ₆ , R ₇ and R ₈ independently represent hydrogen, amino, nitro, cyano, mercapto, halogen, C _1-6 alkylamino, di C _1-6 alkylamino, OR ₁₁ ,- C _1-2 alkyl-OR ₁₁ , SO _q -R ₁₀ , -C _1-2 alkyl -SO _q -R ₁₀ , (C=O)-R ₁₁ , (C=O)-OR ₁₁ , R ₁₀ , C _1-6 alkylthio, C _1-6 alkylaminocarbonyl, C _1-6 alkylcarbonyl C _1-2 alkyl, C _1-6 alkoxycarbonyl C _1-2 alkyl, C _1-6 alkyl aminocarbonyl C _1-2 alkyl, C _1-6 alkylcarbamoyl, C _1-6 alkoxy, aminocarbonyl, C _1-6 alkyl acyloxy, C _1-6 alkylthiocarbonyl, tris C _1-6 alkylsilyl, di C _1-6 alkylphosphono; or R ₇ R ₈ N- represents a six-membered heterocyclic group

   

   

   R ₉ independently represents methyl and ethyl;

   R ₅ and R ₁₀ independently represent unsubstituted or substituted C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, C _1-6 alkoxy C _1-2 alkyl, C _3-6 cycloalkenyl, C _2-6 alkenyl C _1-2 alkyl, C _2-6 alkynyl C _1-2 alkyl, C _3-6 cycloalkyl C _{1 -2} alkyl, C _3-6 cycloalkenyl C _1-2 alkyl, heterocyclic, aryl, heteroaryl, heterocyclic C _1-2 alkyl, aryl C _1-2 alkyl, hetero Aryl C _1-2 alkyl, and the heterocyclic group has 0, 1 or 2 oxo groups; the "substituted" means substituted by 1 to 2 groups selected below: not included Or halogen-containing C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl or C _3-6 cycloalkyl, cyano, cyano C _1-2 alkyl, halogen, mercapto, nitrate Group, cyanothio group, OR ₁₂ , -C _1-2 alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and C _1-6 alkoxy C _1-2 alkoxycarbonyl;

   R ₄ and R ₁₁ independently represent hydrogen, unsubstituted or substituted C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, C _1-6 alkyl Oxygen C _1-2 alkyl, C _3-6 cycloalkenyl, C _2-6 alkenyl C _1-2 alkyl, C _2-6 alkynyl C _1-2 alkyl, C _3-6 cycloalkyl C _1-2 alkyl, C _3-6 cycloalkenyl C _1-2 alkyl, heterocyclyl, aryl, heteroaryl, heterocyclyl C _1-2 alkyl, aryl C _1-2 alkyl , Heteroaryl C _1-2 alkyl, and the heterocyclic group has 0, 1 or 2 oxo groups; "substituted" means substituted by 1 to 2 groups selected from: C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl or C _3-6 cycloalkyl without or containing halogen, cyano, cyano C _1-2 alkyl, halogen, mercapto , Nitro, cyanothio, OR ₁₂ , -C _1-2 alkyl-OR ₁₂ , S(O) _m R ₁₄ , NR ₁₂ R ₁₃ , NR ₁₃ OR ₁₂ , COR ₁₂ , OCOR ₁₂ , SCOR ₁₂ , NR ₁₃ COR ₁₂ , NR ₁₃ COOR ₁₂ , NR ₁₃ SO ₂ R ₁₄ , CO ₂ R ₁₂ , COSR ₁₂ , CONR ₁₂ R ₁₃ and C _1-6 alkoxy C _1-2 alkoxycarbonyl;

   R ₁₂ and R ₁₃ independently represent hydrogen, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, phenyl, Benzyl

   R ₁₄ independently represents C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-6 cycloalkyl, phenyl, and benzyl, which do not contain or contain halogen;

   m and q independently represent 0, 1 or 2, respectively, and n represents 0 or 1.
5. The 4-(3-heterocyclic-1-benzoyl)pyrazole compound or its salt according to claim 1, characterized in that:

   X represents methyl, ethyl, isopropyl, cyclopropyl;

   Y represents hydrogen atom, methyl, ethyl, trifluoromethyl, cyclopropyl;

   Z represents methyl, chlorine, fluorine, cyano, methylsulfonyl;

   Q stands for

   

   among them,

   R ₁ and R ₂ independently represent hydrogen, C _1-6 alkyl, halogenated C _1-6 alkyl, halogen, C _3-6 cycloalkyl, C _1-6 alkoxy, halogenated C _{1- 6} alkoxy, C _1-6 alkoxycarbonyl, phenyl, pyridyl;

   R ₃ represents methyl and ethyl.
6. A method for preparing a 4-(3-heterocyclic-1-benzoyl)pyrazole compound or a salt thereof according to any one of claims 1-5, comprising the steps of:

   

   Acyl halide reaction to obtain compound III, and then esterification reaction with compound IV to prepare the compound represented by general formula I; the reaction equation is as follows:

   

   Among them, Hal represents halogen, preferably chlorine;

   The acyl halogenation reaction is carried out in the presence of a halogenating reagent and a solvent, the reaction temperature is 0-100°C, preferably, the halogenating reagent is dichlorosulfoxide, and the solvent is selected from acetonitrile, DMF, THF, methylene chloride , One or more combinations of dichloroethane; esterification reaction is carried out in the presence of a solvent and a base, the reaction temperature is 0-100 ℃, preferably, the solvent is acetonitrile, DMF, THF, methylene chloride , One or more combinations of dichloroethane, the base is triethylamine, NMM or DIPEA.
7. A herbicide composition comprising a herbicidally effective amount of at least one of the 4-(3-heterocyclyl-1-benzoyl)pyrazole compounds or salts thereof according to any one of claims 1-5 Species.
8. The herbicide composition according to claim 7, which further comprises a formulation adjuvant.
9. A method for controlling weeds, which comprises a herbicidally effective amount of 4-(3-heterocyclyl-1-benzoyl)pyrazole compounds or salts thereof according to any one of claims 1-5 At least one herbicide composition according to claim 7 or 8 is used on plants or weed areas.
10. At least one of the 4-(3-heterocyclic-1-benzoyl)pyrazole compounds or salts thereof according to any one of claims 1-5 or the herbicide according to claim 7 or 8 The use of the composition for controlling weeds. Preferably, the 4-(3-heterocyclic-1-benzoyl)pyrazole compound or its salt is used to control weeds in useful crops. The useful crops are genetically modified crops or crops processed by genome editing technology.