WO2001085907A2

WO2001085907A2 - Herbicidal or plant growth regulatory compositions

Info

Publication number: WO2001085907A2
Application number: PCT/US2001/010810
Authority: WO
Inventors: Jeffrey R. Schussler; Kevin E. Crosby; Patricia A. Backus; Masamitsu Tsukamoto
Original assignee: Ishihara Sangyo Kaisha Ltd
Current assignee: Ishihara Sangyo Kaisha Ltd
Priority date: 2000-05-11
Filing date: 2001-04-17
Publication date: 2001-11-15
Anticipated expiration: 2002-11-11
Also published as: AR028063A1; AU2001256978A8; WO2001085907A3; AU2001256978A1

Abstract

The present invention provides to a herbicidal or plant growth regulatory composition comprising as the effective components A) at least one substituted benzene derivative of the formula (I) or its salt wherein X is halogen or nitro; Y is hydrogen or halogen; W is oxygen or sulphur or imino; R is alkyl, an aryl group which may be substituted, or a heteroaryl group which may be substituted; Q is a heterocyclyl group; and Z is hydrogen, an alkyl group which may be substituted, or an amino group which may be substituted; and B) at least one herbicidal compound selected from the group consisting of aryloxyalkanoic acids, aromatic carboxylic acids, ureas, triazines, anilides, hydroxybenzonitriles, quaternary ammonium salts, diphenyl ethers, triketones, aryloxyphenoxypropionic acids, oximes, sulfonylureas, imidazolinones, dinitroanilines, chloroacetanilides, oxyacetamides, thiocarbamates, isoxazolidinones, quinoline carboxylic acids, isoxazoles, semicarbazones, chlorates and thiadiazoles, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds, urea compounds, tetraoxides and tetraoxosulfates.

Description

HERBICIDAL OR PLANT GROWTH REGULATORY COMPOSITIONS

The present invention relates to a herbicidal or plant growth regulatory composition comprising as the effective components at least one substituted benzene derivative and at least one other specific herbicidal or plant growth regulatory compound.

BACKGROUND OF THE INVENTION WO98/41093 and W099/21837 disclose certain substituted benzene derivatives as active ingredients for herbicides.

On the other hand, most of other specific herbicidal or plant growth regulatory compounds have been known as active ingredients for herbicides or plant growth regulators.

SUMMARY OF THE INVENTION The present invention provides to a herbicidal or plant growth regulatory composition comprising as the effective components A) at least one substituted benzene derivative of the formula I or its salt:

wherein X is halogen or nitro;

Y is hydrogen or halogen; W is oxygen or sulphur or imino;

R is alkyl, an aryl group which may be substituted, or a heteroaryl group which may be substituted;

Q is a heterocyclyl group; and

Z is hydrogen, an alkyl group which may be substituted, or an amino group which may be substituted; with a proviso that l-amino-3-[4-chloro-2-fluoro-5-(3-nitro-2-pyridyloxy)phenyl]-6-trifluoromethyl-l,2,3,4-tetrahyd ropyrimidine-2,4-dione is excluded; and

B) at least one herbicidal compound selected from the group consisting of aryloxyalkanoic acids, aromatic carboxylic acids, ureas, triazines, anilides, hydroxybenzonitriles, quaternary ammonium salts, diphenyl ethers, triketones, aryloxyphenoxypropionic acids, oximes, sulfonylureas, imidazolinones, dinitroanilines, chloroacetanilides, oxyacetamides, thiocarbamates, amides, isoxazolidinones, quinoline carboxylic acids, isoxazoles, semicarbazones, chlorates and thiadiazoles, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds, urea compounds, tetraoxides and tetraoxosulfate. DETAILED DESCRIPTION OF THE INVENTION In the above definitions, the term halogen includes fluorine, chlorine, bromine, or iodine. The term alkyl includes straight chain or branched alkyls containing 1-8 carbon atoms. The term aryl includes phenyl or naphthyl. The term heteroaryl includes an aromatic ring containing 1-4 heteroatoms which is selected from the group consisting of oxygen, nitrogen and sulfur, and may for example be furanyl, pyridyl, thienyl, pyrimidinyl, benzofuranyl, quinolyl, benzothienyl, quinoxalyl, and the like. The substituents for aryl and heteroaryl groups may, for example, be halogen, cyano, nitro, a ino, carboxyl, (Cι_-4)alkyl, halo(Cι.₄)alkyl, (Cι_₄)alkylsilyl, (Ci^alkylcarbonyl,

(C_1-4)alkoxy, (Cι- )alkoxycarbonyl, halo(C_1- )alkoxy, halo(C_1- )alkoxycarbonyl, (C_1-4)alkylsulfonyl, halo(C_1-4)alkylsulfonyl, aryl, heteroaryl, (C_3-6)cycloalkyl and the like. Examples of the heterocyclyl group are as follows:

Q1 Q2 Q3 Q4

Q5 Q6 Q7 Q8

Q13 Q14 Q15 ^Q16

Q17 Q18 Q19 Q20

Q21 Q22 Q23 Q24 wherein Ri is hydrogen, (Cι-₄)alkyl, halo(Cι_-4)alkyl, (C_2-4)alkenyl, (C_2-4)alkynyl, amino, (C_1- )alkoxy(C_1-4)alkyl, acetyl,

(C_1- )alkylcarbonylamino or (C ₁ )alkoxycarbonyl; R₂ is (C_1-4)alkyl, halo(Cι_-4)alkyl, (Cw)alkoxy or halo(C_1- )alkoxy;

R₃ is hydrogen, halogen, nitro, amino, (C_1-4)alkylamino, halo(C_1- )alkylamino, cyano or amide; R_\ and R₂ can take together to make ring. each of R and R₅ is oxygen, sulfur or imino;

Q6, Q7, Q10, Q16 or Q17 maybe unsaturated containing one or two double bonds in the 6-membered ring.

The substituents for alkyl and amino groups may, for example, be halogen, (Ci^alkyl, (C_2- )alkenyl, (C_2-4)alkynyl, amino, (C_3-6)cycloalkyl, hetero(C_3-6)cycloalkyl, (C_1-4)alkylsulfonyl, arylsulfonyl, benzyl, aryl, heteroaryl, (Ci^alkylcarbonyl, aryloxy(C_1- )alkylcarbonyl, (C_2- )alkenylcarbonyl, (C_2-4)alkynylcarbonyl, (C_3-6)cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C_1-4)alkoxycarbonyl, (C_1-4)alkylthiocarbonyl, (C_3-6)cycloalkyloxycarbonyl, benzyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl, aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl, (C_1- )alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl,

arylcarbonylcarbonyl and the like; where any of these groups maybe substituted with any of the functional groups represented by one or more of the following: halogen, cyano, nitro, amino, carboxyl,- (C_1-4)alkyl, halo(C_1-4)alkyl, (C_1-4)alkylsilyl, (C_1- )alkylcarbonyl, halo(C_1-4)alkylcarbonyl, (C^alkoxy, (C_1-4)alkoxycarbonyl, halo(C_1- )alkoxy, halo(C_1-4)alkoxycarbonyl, (C_1- )alkylsulfonyl, halo(C_1-4)alkylsulfonyl, aryl, heteroaryl, (C_3-6)cycloalkyl, and the like.

The compounds of the formula I may form salts with acidic substances or basic substances. Salts with acidic substances may be inorganic acid salts such as a salt of hydrochloride or hydrobromide, a phosphate, a sulfate or a nitrate. Salts with basic substances may be salts of inorganic or organic bases such as a sodium salt, a potassium salt, a calcium salt, or quarternary ammonium salts such as an ammonium salt or a dimethylamine salt.

The compounds of the formula I may exist as geometrical or optical isomers and the compounds include all of these isomeric forms.

Preferred compositions of the present invention are as follows. (1) The effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is halogen such as fluorine, chlorine, bromine, or iodine; Y is hydrogen or halogen such as fluorine, chlorine, bromine, or iodine;

W is oxygen or sulphur;

R is an aryl or heteroaryl group in which these groups may be substituted with halogen, cyano, nitro, amino, carboxyl, (C_1-4)alkyl, halo(Cι_^t)alkyl, (Cι-₄)alkylsilyl, (C_1- )alkylcarbonyl, halo(C_1- )alkylcarbonyl, (C_1- )alkoxy, (C_1-4)alkoxycarbonyl, halo(C_1-4)alkoxy, halo(C_1-4)alkoxycarbonyl, (Ci^alkylsulfonyl, halo(C_1- )alkylsulfonyl, aryl, heteroaryl, or (C_3-6)cycloalkyl;

Q is Ql, Q3, Q4, Q5, Q6, Q7, Q8, Q16 or Q17; wherein R_ls R₂, R₃, * and R₅ are as defined above; and

Z is hydrogen; with a proviso that l-amino-3-[4-chloro-2-fluoro-5-(3-nitro-2-pyridyloxy)phenyl]-6-trifluoromethyl-l,2,3,4-tetrahyd ropyrimidine-2,4-dione is excluded; and

B) at least one herbicidal compound selected from the group consisting of aryloxyalkanoic acids such as 2,4-D, 2,4-DB, MCPA or MCPB; aromatic carboxylic acids such as 2,3,6-TBA, Dicamba Picloram or Clopyralid; ureas such as Diuron, Linuron, Isoproturon, Chlorotoluron,

Metobenzuron, Tebuthiuron or Fluometuron; triazines such as Simazine, Atrazine, Cyanazine, Terbuthylazine, Atraton, Hexazinone, Metribuzin, Simetryn, Ametryn Prometryn, Dimethametryn or Triazifiam; anilides such as Propanil, Cypromid or Cyclanilide; hydroxybenzonitriles such as Bromoxynil-octanoate, Bromoxynil or Ioxynil; quaternary ammonium salts such as Paraquat, Paraquat-dichlorid, Diquat or Difenzoquat; diphenyl ethers such as Lactofen, Acifluorfen, Acifluorfen-sodium, Oxyfluorfen, Fomesafen, Bifenox or Chlomethoxyfen; triketones such as Sulcotrione or Mesotrione; aryloxyphenoxypropionic acids such as Diclofop-methyl, Pyrofenop-sodium, Fluazifop-butyl, Fluazifop-p-butyl, Haloxyfop-methyl, Quizalofop-p-ethyl, Quizalafop-p-tefuryl, Fenoxaprop-ethyl, Fenoxaprop-p-ethyl or Clodinafpop-p-propargyl; oximes such as Alloxydim-sodium, Sethoxydim, Clethodim, Tepraloxydim Tralkoxydim or Cycloxydium; sulfonylureas such as Chlorimuron-ethyl, Nicosulfuron, Metsulfuron-methyl, Triasulfuron, Primisulfuron-methyl, Tribenuron-methyl, Chlorosulfuron, Bensulfuron-methyl, Sulfometuron-methyl, Prosulfuron, Halosulfuron, Halosulfuron-methyl, Thifensulfuron-methyl, Rimsulfuron, Azimsulfuron,

Flazasulfuron, Imazosulfuron, Cyclosulfamuron, Flupyrsulfuron, Iodosulfuron, Ethoxysulfuron, Flucarbazone, Sulfosulfuron, Oxasulfuron or Foramsulfuron; imidazolinones such as Imazapyr, Imazethapyr, Imazaquin, hnazamox, Imazameth or lmazamethabenz-methyl; dinitroanilines such as Trifluralin, Oryzalin, Pendimethalin, Ethalfluralin, Benfiuralin or Prodiamine; chloroacetanilides such as Alachlor, Metolachor Metolachor-S, Propachlor, Acetochlor,

Acetochlor-S, Propisochlor or Dimethenamid; oxyacetamides such as Flufenacet; thiocarbamates such as Thiobencarb, EPTC, Triallate, Molinate, Pebulate, Cycloate, Butylate, Vernolate or Prosulfocarb; amides such as Diphenamid; isoxazolidinones such as Clomazone; quinoline carboxylic acids such as Quinclorac; isoxazoles such as Isoxaflutole; semicarbazones such as Diflufenzopyr; chlorates such as sodium chlorate, and thiadiazoles such as Fluthiacet-methyl, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds such as ethephone, tribufos; urea compounds such as thiadiazuron; tetraoxides such as dimethipin and tetraoxosulfates such as AMADS.

(2) The effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is halogen such as fluorine, chlorine, bromine, or iodine;

Y is hydrogen or halogen such as fluorine, chlorine, bromine, or iodine;

W is oxygen or sulphur; R is alkyl;

Q is Ql, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10 or Ql 1; wherein R_u R₂, R₃, R-j and R₅ are as defined above; and

Z is an alkyl or amino group in which these groups may be substituted with halogen, (Cι-₄)alkyl, (C_2- )alkenyl, (C_2- )alkynyl, amino, (C_3-6)cycloalkyl, hetero(C_3-6)cycloalkyl, (C_1- )alkylsulfonyl, arylsulfonyl, benzyl, aryl, heteroaryl, (C_1-4)alkylcarbonyl, aryloxy-(C_1-4)alkylcarbonyl, (C_2- )alkenylcarbonyl, (C₂^)alkynylcarbonyl, (C_3-6)cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C_1-4)alkoxycarbonyl, (C_1- )alkylthiocarbonyl, (C_3-6)cycloalkyloxycarbonyl, benzyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl, aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl, (C _1- )alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl, (C_1- )alkoxycarbonylcarbonyl or arylcarbonylcarbonyl; where any of these groups maybe substituted with any of the functional groups represented by one or more of the following: halogen, cyano, nitro, amino, carboxyl, ( -^alkyl, halo(C_1- )alkyl, (C_1-4)alkylsilyl,

halo(Cι_-4)alkylcarbonyl,

alo(Cι- )alkoxy, halo(Cι_-4)alkoxycarbonyl, (C_1-4)alkylsulfonyl,

aryl, heteroaryl, or (C_3-6)cycloalkyl; and

Metobenzuron, Tebuthiuron or Fluometuron; triazines such as Simazine, Atrazine, Cyanazine, Terbuthylazine, Atraton, Hexazinone, Metribuzin, Simetryn, Ametryn, Prometryn, Dimethametryn or Triaziflam; anilides such as Propanil, Cypromid or Cyclanilide; hydroxybenzonitriles such as Bromoxynil-octanoate, Bromoxynil or Ioxynil; quaternary ammonium salts such as Paraquat, Paraquat-dichlorid, Diquat or Difenzoquat; diphenyl ethers such as Lactofen, Acifluorfen, Acifluorfen-sodium, Oxyfluorfen, Fomesafen, Bifenox or Chlomethoxyfen; triketones such as Sulcotrione or Mesotrione; aryloxyphenoxypropionic acids such as Diclofop-methyl, Pyrofenop-sodium, Fluazifop-butyl, Fluazifop-p-butyl, Haloxyfop-methyl, Quizalofop-p-ethyl, Quizalafop-p-tefuryl, Fenoxaprop-ethyl, Fenoxaprop-p-ethyl or Clodinafpop-p-propargyl; oximes such as Alloxydim-sodium, Sethoxydim, Clethodim, Tepraloxydim Tralkoxydim or Cycloxydium; sulfonylureas such as Chlorimuron-ethyl, Nicosulfuron, Metsulfuron-methyl, Triasulfuron, Primisulfuron-methyl, Tribenuron-methyl, Chlorosulfuron, Bensulfuron-methyl, Sulfometuron-methyl, Prosulfuron, Halosulfuron, Halosulfuron-methyl, Thifensulfuron-methyl, Rimsulfuron, Azimsulfuron, Flazasul uron, Imazosulfiiron, Cyclosulfamuron, Flupyrsulfiiron, lodosulfuron, Ethoxysulfuron, Flucarbazone, Sulfosulfuron, Oxasulfuron or Foramsulfuron; imidazolinones such as Imazapyr, Imazethapyr, Imazaquin, hnazamox, hnazameth or Imazamethabenz-methyl; dinitroanilines such as Trifluralin, Oryzalin, Pendimethalin, Ethalfluralin, Benfluralin or Prodiamine; chloroacetanilides such as Alachlor, Metolachor Metolachor-S, Propachlor, Acetochlor, Acetochlor-S, Propisochlor or Dimethenamid; oxyacetamides such as Flufenacet; thiocarbamates such as Thiobencarb, EPTC, Triallate, Molinate, Pebulate, Cycloate, Butylate, Vernolate or Prosulfocarb; amides such as Diphenamid; isoxazolidinones such as Clomazone; quinoline carboxylic acids such as Quinclorac; isoxazoles such as Isoxaflutole; semicarbazones such as Diflufenzopyr, chlorates such as sodium chlorate, and thiadiazoles such as Fluthiacet-methyl, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds such as ethephone, tribufos; urea compounds such as thiadiazuron; tetraoxides such as dimethipin and tetraoxosulfates such as AMADS.

More preferred compositions of the present invention are as follows.

(1) The effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is halogen such as fluorine, chlorine, bromine, or iodine; Y is halogen such as fluorine, chlorine, bromine, or iodine; W is oxygen or sulphur;

R is an aryl or heteroaryl group in which these groups may be substituted with halogen, cyano, nitro, amino, carboxyl, (C_1- )alkyl, halo(Cι_-4)alkyl, (C_1-4)alkylsilyl, (C_1-4)alkylcarbonyl, halo(C_1- )alkylcarbonyl, (C_1- )alkoxy, (d-^alkoxycarbonyl, halo(C_1- )alkoxy, halo(C_1-4)alkoxycarbonyl, (C_1- )alkylsulfonyl, halo(C_1- )alkylsulfonyl, aryl, heteroaryl, or (C_3-6)cycloalkyl;

Q is Ql; R_! is amino; R₂ is halo(C_1-4)alkyl; R₃ is hydrogen; each of R and R₅ is oxygen; and Z is hydrogen; with a proviso that l-amino-3-[4-chloro-2-fluoro-5-(3-nitro-2-pyridyloxy)phenyl]-6-trifluoromethyl-l,2,3,4-tetrahyd ropyrimidine-2,4-dione is excluded; and

B) at least one herbicidal compound selected from the group consisting of aryloxyalkanoic acids such as 2,4-D or MCPA; aromatic carboxylic acids such as Dicamba or Clopyralid; ureas such as Diuron, Linuron or Metobenzuron; triazines such as Simazine, Atrazine, Cyanazine, Terbuthylazine, Metribuzin or Ametryn; anilides such as Propanil, Cypromid or Cyclanilide; hydroxybenzonitriles such as Bromoxynil-octanoate or Bromoxynil; quaternary ammonium salts such as Paraquat; diphenyl ethers such as Oxyfluorfen; triketones such as Sulcotrione or Mesotrione; sulfonylureas such as Nicosulfuron, Primisulfuron-methyl Prosulfuron, Thifensulfuron-methyl, Rimsulfuron or Foramsulfuron; imidazolinones such as hnazethapyr; dinitroanilines such as Trifluralin or Pendimethalin; chloroacetanilides such as Alachlor, Metolachor Metolachor-S, Propachlor, Acetochlor or Dimethenamid; oxyacetamides such as Flufenacet; thiocarbamates such as EPTC or Butylate; isoxazolidinones such as Clomazone; quinoline carboxylic acids such as Quinclorac; isoxazoles such as Isoxaflutole; semicarbazones such as Diflufenzopyr, chlorates such as sodium chlorate, and thiadiazoles such as Fluthiacet-methyl, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds such as ethephone, tribufos; urea compounds such as thiadiazuron; tetraoxides such as dimethipin and tetraoxosulfates such as AMADS.

(2) The effective components are A) at least one substituted benzene derivative of the formula I or its salt wherein X is halogen such as fluorine, chlorine, bromine, or iodine; Y is halogen such as fluorine, chlorine, bromine, or iodine; W is oxygen or sulphur; R is alkyl; Q is Ql ; R\ is (C_1- )alkyl; R₂ is halo(C_1- )alkyl; R is hydrogen; each of and R₅ is oxygen; and

Z is an alkyl or amino group in which these groups may be substituted with halogen, (Ci-^alkyl, (C_2- )alkenyl, (C_2- )alkynyl, amino, (C_3-6)cycloalkyl, hetero(C_3-6)cycloalkyl, (Cι^)alkylsulfonyl, arylsulfonyl, benzyl, aryl, heteroaryl, (Cι- )alkylcarbonyl, aryloxy-(C_1- )alkylcarbonyl, (C_2-4)alkenylcarbonyl, (C_2- )alkynylcarbonyl,

(C_3-6)cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl,

(C_1-4)alkylthiocarbonyl, (C_3-6)cycloalkyloxycarbonyl, benzyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl, aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl,

arylaminocarbonyl, heteroarylaminocarbonyl,

or arylcarbonylcarbonyl; where any of these groups may be unsubstituted or substituted with any of the functional groups represented by one or more of the following: halogen, cyano, nitro, amino, carboxyl, (C_1- )alkyl, halo(C_1-4)alkyl,

(C_1-4)alkylcarbonyl, halo(C_1-4)alkylcarbonyl, (C )alkoxy, (C_1-4)alkoxycarbonyl, halo(C_1-4)alkoxy, halo(C_1-4)alkoxycarbonyl, (C_1-4)alkylsulfonyl, halo(C_1- )alkylsulfonyl, aryl, heteroaryl, or (C_3-6)cycloalkyl; and

B) at least one herbicidal compound selected from the group consisting of aryloxyalkanoic acids such as 2,4-D or MCPA; aromatic carboxylic acids such as Dicamba orQopyralid; ureas such as Diuron, Linuron or Metobenzuron; triazines such as Simazine, Atrazine, Cyanazine, Terbuthylazine, Metribuzin or Ametryn; anilides such as Propanil, Cypromid or Cyclanilide; hydroxybenzonitriles such as Bromoxynil-octanoate or Bromoxynil; quaternary ammonium salts such as Paraquat; diphenyl ethers such as Oxyfluorfen; triketones such as Sulcotrione or Mesotrione; sulfonylureas such as Nicosulfuron, Primisulfuron-methyl, Prosulfuron, Thifensulfuron-methyl, Rimsulfuron or Foramsulfuron; imidazolinones such as hnazethapyr; dinitroanilines such as Trifluralin or Pendimethalin; chloroacetanilides such as Alachlor, Metolachor Metolachor-S, Propachlor, Acetochlor or Dimethenamid; oxyacetamides such as Flufenacet; thiocarbamates such as EPTC or Butylate; isoxazolidinones such as Clomazone; quinoline carboxylic acids such as Quinclorac; isoxazoles such as Isoxaflutole; semicarbazones such as Diflufenzopyr, chlorates such as sodium chlorate and thiadiazoles such as Fluthiacet-methyl, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds such as ethephone, tribufos; urea compounds such as thiadiazuron; tetraoxides such as dimethipin and tetraoxosulfates such as AMADS.

Most preferred compositions of the present invention are as follows. (1) The effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is chlorine; Y is fluorine; W is oxygen; R is phenyl or pyrimidinyl in which these groups may be substituted with cyano or nitro; Q is Q 1 ; R is amino; R₂ is halo(C_1-4)alkyl; R₃ is hydrogen; each of j and R₅ is oxygen; and Z is hydrogen; and B) at least one herbicidal compound selected from the group consisting of triazines such as Atrazine; dinitroanilines such as Pendimethalin; chloroacetanilides such as Alachlor, Metolachor Metolachor-S, Acetochlor or Dimethenamid; and oxyacetamides such as Flufenacet, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds such as ethephone, tribufos; urea compounds such as thiadiazuron; tetraoxides such as dimethipin and tetraoxosulfates such as AMADS.

(2) The effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is chlorine; Y is fluorine; W is oxygen; R is alkyl; Q is Ql; Ri is (C_1-4)alkyl; R₂ is halo(C_1-4)alkyl; R₃ is hydrogen; each of R and R₅ is oxygen; and Z is (C_1- )alkoxycarbonyl-alkyl which maybe substituted with halogen, arylcarbonyl-amino, aryloxy-(C_1- )alkylcarbonyl-amino which may be substituted with nitro, or benzyloxycarbonyl-amino which may be substituted with nitro; and B) at least one herbicidal compound selected from the group consisting of triazines such as Atrazine; dinitroanilines such as Pendimethalin; chloroacetanilides such as Alachlor, Metolachor Metolachor-S, Acetochlor or Dimethenamid; and oxyacetamides such as Flufenacet, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds such as ethephone, tribufos; urea compounds such as thiadiazuron and tetroxides such as dimethipin. The substituted benzene derivatives of the formula I include those as shown in the following Table 1.

Table 1

No X Y W R Q R. R₂ R₃ R4 R₅ z

A-l Cl F o phenyl -SL . NH₂ CF_{3 t} H 0 0 H

A-2 Cl o 2-nιtro-phenyl Q¹ . NH₂ CF₃ _^ H 0 o _Λ H

A-3 Cl . ^F , o 2-cyano-phenyl , NH₂ CF₃ __ H 0 o H

A-4 Cl . ^F , 0 3-ιutro-2-pyπdyl Q , NH₂ , ^CF3 _r H 0 o •> H

A-5 Cl _ F _ 0 2-pyπmιdιnyl i . NH₂ CF_{3 r} H 0 0 _ H

A-6 Cl . ^F - 0 2-pyπιmdιnyl Q3 . CH₃ CF₃ . ^cl - - H

A-7 Cl F _ o 2-pyramdmyl Q3 CH₃ CF₃ Br - - H

A-8 Cl F _ o 2-pynmιduιyl Q3 _ CH₃ OCHF₂ Cl - - H

A-9 Cl F _ o 2-pyπιmdιnyl Q4 . (CH₂)₃F - - - - H

A-10 Cl _ F _ o 2-pyπmιdιnyl Q5 . CHF₂ CH₃ - - - H

A-ll Cl _ F _ o 2-pyπmιdιnyl Q6 _ - - - s 0 H

A-12 Cl F _ o 2-pyππudmyl . - - - s 0 H

A-13 Cl F o 2-pyrιmιdιnyl Q8 . H CF₃ - - H

A-14 Cl , ^F , o 2-pyπιmdιnyl Q⁸ , CH₃ CF₃ - H

A-15 Cl F < o 2-pyπmιdιnyl ςi6 _ - Cl - - H

A-16 Cl F _* o 2-pyπmιdιnyl Q17 _^ - - - 0 - H

A-17 . ^cl F ; 0 CH₃ ! CH₃ CF₃ H 0 0 CH₂CH₂C1C0₂C₂H₅

A-l 8 Cl F _ o CH₃ ¹ , CH₃ CF₃ _ H 0 0 ^' 2-naphthoylammo

A-19 Cl F o CH₃ Ql CH₃ CF₃ H 0 0 3-nιtrobenzyloxy-carb

_{* *} onylammo

A-20 Cl F o CH₃ Ql CH₃ CF₃ H 0 0 3 -nttrophenoxyacetyl- amino

A-21 Cl F _ o CH₃ 2 . - - - - - 2-naphthoylamιno

A-22 Cl F 0 CH₃ Q3 CH₃ OCHF₂ Cl - - 3-nιtrobenzyloxy-carb onylammo

A-23 Cl F o CH₃ Q3 ! CH₃ CF₃ Br 3-nιtrobenzyloxy-carb onylammo

*

A-24 Cl F O ' CH₃ ^; 4 I (CH₂)₃F ~ ! - — 2-naphthoylamιno

A-25 Cl ^F . o CH₃ , Q5 CH₃ OCHF₂ - — ¹ 3-mtrobenzyloxy-carb onylammo

A-26 Cl F . o CH₃ 6 ; - - - s 0 2-naphthoylammo

A-27 Cl F o CH₃ 7 , - fr s ^" o benzoylamino

A-28 Cl F _* o CH₃ 8 , H CF₃ — - * 2-naphthoylamιno

A-29 Cl F ' o ' CH₃ ^■ Q⁸ : CH₃ CF₃ : _ 2-naphthoylammo

A-30 Cl F , O ! CH₃ i ^Q9 i H CF₃ ^j Cl - _* 2-naρhthoylamιno

A-31 Cl F . o ! CH₃ . Qio ; - ~ ' - 0 s : 2-naphthoylammo

A-32 Cl F ' o CH₃ : QH ^' - - ' - - _— 2-naphthoylamιno Other specific herbicidal or plant growth regulatory compounds include those as shown in the following Table 2.

Table 2

The blend ratio and total dose of one substituted benzene derivative and one other specific herbicidal compound or plant growth regulatory compound can not generally be defined, since they vary depending on kind of compound, the time, place and method of application, weather conditions, soil type and type of formulation. However one other specific herbicidal compound or plant growth regulatory compound may be incorporated usually in an amount of 0.001 to 2000 parts by weight, preferably 0.005 to 500 parts by weight, per one part by weight of one substituted benzene derivative. Further, the total dose of all of the active ingredients is usually from 1 to 10000 g ha, preferably from 5 to 2000 g/ha. The present invention covers such herbicidal or plant growth regulatory compositions.

The compositions of the present invention exhibit synergistic effects. The compositions can be used for a wide range of applications, for example on crop lands such as paddy fields, upland farms, orchards and mulberry fields, and non-crop lands such as forests, farm roads, playgrounds, and factory sites. They can also be used in a wide range of application, as plant growth regulator for defoliating crop plants such as cotton, potato and the like, and causing uniform boll opening, or for desiccating these crop vines, and for controlling the growth of some plants. The application method may be suitably selected for soil treatment application and foliar application.

The defoliation or desiccation composition can be mentioned preferably a combination of A) at least one substituted benzene derivative and B) at least one herbicidal or plant growth regulatory compound selected from the group consisting of ethephon, dimethipin, tribufos, cyclanilide, thiadiazuron, paraquat, sodium chlorate, sulfuric acid and AMADS as effective defoliants of cotton or as effective desiccants of crop foliage.

The active ingredients are formulated with inert ingredients known to the art to facilitate either the suspension, dissolution or emulsification of the active ingredients for the desired use. The type of formulation prepared recognizes the facts that formulation, crop and use pattern all can influence the activity and utility of the active ingredients in a particular use. Thus for agricultural use the present compositions may be formulated as water dispersible granules, granules for direct application to soils, water soluble concentrates, wettable powders, dusts, solutions, emulsifiable concentrates (EC), microemulsion, suspoemulsion, invert emulsion or other types of formulations, depending on the desired weed targets, crops and application methods.

These formulations may be applied to the target area (where suppression of unwanted vegetation is the objective) as dusts, granules or water or solvent diluted sprays. These formulation may contain as little as 0.1% to as much as 97% active ingredients by weight.

Dusts are admixtures of the active ingredients with finely ground materials such as clays (some examples include kaolin and montmorillonite clays), talc, granite dust or other organic or inorganic solids which act as dispersants and carriers for the active ingredient; these finely ground materials have an average particle size of less than 50 microns. A typical dust formulation will contain 1 % active ingredient and 99% carrier.

Wettable powders are composed of finely ground particles which disperse rapidly in water or other spray carriers. Typical carriers include kaolin clays, Fullers earth, silicas and other absorbent, wettable inorganic materials. Wettable powders can be prepared to contain from 1 to 90% active ingredient, depending on the desired use pattern and the absorbability of the carrier. Wettable powders typically contain wetting or dispersing agents to assist dispersion in water or other carriers.

Water dispersible granules are granulated solids that freely disperse when mixed in water. This formulation typically consists of the active ingredients (0.1% to 95% active ingredient), a wetting agent (1-15% by weight), a dispersing agent (1 to 15% by weight) and an inert carrier (1-95% by weight). Water dispersible granules can be formed by mixing the ingredients intimately then adding a small amount of water on a rotating disc (said mechanism is commercially available) and collecting the agglomerated granules. Alternatively, the mixture of ingredients may be mixed with an optimal amount of liquid (water or other liquid) and passed through an extruder (said mechanism is commercially available) equipped with passages which allow for the formation of small extruded granules. Alternatively, the mixture of ingredients can be granulated using a high speed mixer (said mechanism is commercially available) by adding a small amount of liquid and mixing at high speeds to affect agglomeration. Alternatively, the mixture of ingredients can be dispersed in water and dried by spraying the dispersion through a heated nozzle in a process known as spray drying (spray drying equipment is commercially available). After granulation the moisture content of granules is adjusted to an optimal level (generally less than 5%) and the product is sized to the desired mesh size.

Granules are granulated solids that do not disperse readily in water, but instead maintain their physical structure when applied to the soil using a dry granule applicator. These granulated solids maybe made of clay, vegetable material such as corn cob grits, agglomerated silicas or other agglomerated organic or inorganic materials or compounds such as calcium sulfate. The formulation typically consists of the active ingredient (1 to 20%) dispersed on or absorbed into the granule. The granule may be produced by intimately mixing the active ingredients with the granules with or without a sticking agent to facilitate adhesion of the active ingredients to the granule surface, or by dissolving the active ingredients in a solvent, spraying the dissolved active ingredients and solvent onto the granule then drying to remove the solvent. Granular formulations are useful where m-furrow or banded application is desired.

Emulsifiable concentrates (EC) are homogeneous liquids composed of a solvent or mixture of solvents such as xylenes, heavy aromatic naphthas, isophorone or other proprietary commercial compositions derived from petroleum distillates, the active ingredient and an emulsifying agent or agents. The EC is added to water (or other spray carrier) and applied as-a spray to the target area. The composition of an EC formulation can contain 0.1% to 95% active ingredient, 5 to 95% solvent or solvent mixture and 1 to 20% emulsifying agent or mixture of emulsifying agents. Suspension concentrate (also known as flowable) formulations are liquid formulations consisting of a finely ground suspension of the active ingredient in a carrier, typically water or a non-aqueous carrier such as an oil. Suspension concentrates typically contain the active ingredients (5 to 50% by weight), carrier, wetting agent, dispersing agent, anti-freeze, viscosity modifiers and pH modifiers. For application, suspension concentrates are typically diluted with water and sprayed on the target area.

Solution concentrates are solutions of the active ingredient (1 to 70%) in solvents which have sufficient solvency to dissolve the desired amount of active ingredients. Because they are simple solutions without other inert ingredients such as wetting agents, additional additives are usually added to the spray tank mix before spraying to facilitate proper application.

Microemulsions are solutions consisting of the active ingredients (1 to 30%) dissolved in a surfactant or emulsifier, without any additional solvents. There are no additional solvents added to this formulation. Microemulsions are particularly useful when a low odor formulation is required such as in residential turfgrass applications.

Suspoemulsions are combinations of two active ingredients. One active ingredient is made as a suspension concentrate (1-50% active ingredient) and the second active ingredient is made as a emulsifiable concentrate (0.1 to 20%) . A reason for making this kind of formulation is the inability to make an EC formulation of the first ingredient due to poor solubility in organic solvents. The suspoemulsion formulation allows for the combination of the two active ingredients to be packaged in one container, thereby minimizing packaging waste and giving greater convenience to the product user.

The compositions of the present invention may be used in admixture with or in combination with other agricultural chemicals, fertilizers, adjuvants, surfactants, emulsifiers, oils, polymers or phytotoxicity-reducing agents such as herbicide safeners. In such a case, they may exhibit even better effects or activities. As other agricultural chemicals, herbicides, fungicides, antibiotics, plant hormones, plant growth regulators, insecticides, acaricides or nematicides may, for example, be mentioned. Certain tank mix additives such as spreader stickers, penetration aids, wetting agents, surfactants, emulsifiers, humectants and UN protectants may be added in amounts of 0.01% to 5% to enhance the biological activity, stability, wetting, spreading on foliage or uptake of the active ingredients on the target area or to improve the suspensibility, dispersion, redispersion, emulsifiability, UN stability or other physical or physico-chemical property of the active ingredients in the spray tank, spray system or target area. A few formulation examples of the present invention are given as follows.

Formulation example 1. Emulsifiable Concentrate

Each of compound A-l to A-32 0.1-95 % wt./wt.

Each of compound B-l to B-50 0.1-95 % wt./wt.

Calcium sulfonate and nonionic surfactant blend 4-12 % wt./wt.

Aromatic hydrocarbon QS to 100%

Formulation example 2. Suspension Concentrate

Each of compound A-l to A-32 1-70 % wt./wt.

Each of compound B-l to B-50 1-70 % wt./wt.

Proylene gylcol 3-6 % wt./wt.

Silicone defoamer 0.2-1 % w t.

Xanthan gum 0.1-0.3 % wt./wt.

Napthalene formaldehyde condensate 2-6 % wt wt.

Octylphenol ethoxylate 1-4 % wt/wt

1,2 benziso-thiazolin-3-one 0.05-0.25 % wt/wt.

Water QS to 100 %

Formulation example 3. Wettable Powder Each of compound A-l to A-32 1-90 % wt/wt. Each of compound B-l to B-50 1-90 % wt/wt. Sodium -N-methyl-N-oleoyl taurate 1-4 % wt/wt. Napthalene Sulfonate 4-10 % wt/wt Kaolin clay QS to 100%

Formulation example 4. Water Dispersible Granule

Each of compound A-l to A-32 -0.1-95 % wt/wt

Each of compound B-l to B-50 0.1-95 % wt/wt.

Napthalene formaldehyde condensate 3-10 % wt/wt.

Sodium alkyl napthalene sulfenate 1-4 % wt/wt.

Kaolin Clay QS to 100% Test Example 1

Seeds of weed species were sown in 10 cm square plastic pots containing a 3:2:1 sand: soil :peat mixture. Species included two broadleaf weeds, CASOB (Cassia obtusifolia, L., sicklepod) and IPOHE (Ipomoea hederacea, L., ivyleaf morningglory) and one grass weed, SORHA (Sorghum halepense, johnsongrass). Herbicide treatments were applied in water carrier via automated track sprayer to the soil surface of these pots lday after planting. The sprayer was calibrated to deliver the material in a volume of 1871 ha through a TJ8001E spray nozzle at a pressure of 40 PSI.

Treatments included experimental test materials and commercially available herbicides. Compounds were applied alone and in combination in order to evaluate the potential for synergistic herbicide efficacy as described by Colby (Colby, S.R. 1967. Calculating synergistic and antagonistic responses of herbicide combinations. Weeds 15:20-22).

After treatment, pots were returned to a greenhouse where they were watered and held in good growth conditions for two weeks. At the end of two weeks, herbicidal efficacy was evaluated visually using a rating system from 0-100%, where 0 = no inhibition of growth, and 100 = complete death of all plants in the testing unit.

Efficacy of individual compounds X and Y were used to calculate the efficacy expected (E) for additive herbicide action. If the observed efficacy exceeded this value, then the combination of X and Y is concluded to be synergistic in nature. E = X + Y- (XxY/100)

Synergistic efficacy responses are shown for several compounds in Tables 3-4.

Table 3

Test Example 2

Seeds of weed species were sown in 10 cm square plastic pots containing a 3:2:1 sand: soil :peat mixture. Species included four broadleaf weeds, CASOB (Cassia obtusifolia, L., sicklepod), IPOHE (Ipomoea hederacea, L., ivyleaf morningglory), AMBEL (Ambrosia artemisiifolia L. , common ragweed) and XANST (Xanthium strumarium L. , common cocklebur), and one grass weed, SETVI (Setaria viridis, L., green foxtail). Herbicide treatments were applied in water carrier via automated track sprayer to the soil surface of three replicate pots/treatment lday after planting. The sprayer was calibrated to deliver the material in a volume of 187 1/ha through a TJ8001E spray nozzle at a pressure of 40 PSI. Treatments included experimental test materials and commercially available herbicides.

Compounds were applied alone and in combination in order to evaluate the potential for synergistic herbicide efficacy as described by Colby (Colby, S.R. 1967. Calculating synergistic and antagonistic responses of herbicide combinations. Weeds 15:20-22).

Efficacy of individual compounds X and Y were used to calculate the efficacy expected (E) for additive herbicide action. If the observed efficacy exceeded this value, then the combination of X and Y is concluded to be synergistic in nature.

E = X + Y- (X*Y/100) Synergistic efficacy responses are shown in Tables 5-9.

Test Example 3

A greenhouse bioassay screening system was used to evaluated the defoliation ability of the test compounds. Cotton (Gossyium hirsutum L.) was used as the test species. Seeds of cotton were sown in 10 cm square plastic pots containing a 3:2:1 sand:soil:peat mixture. Plants were treated for defoliation when 4-5 fully expanded leaves (not counting cotyledonary leaves) were present.

Treatments included experimental test materials and commercially available cotton defoliants and harvest aids. Test materials were formulated either as emulsifiable concentrates (EC) formulations or dissolved in acetone. Test materials were applied at rates ranging from 7.8g a.i./ha to 150g a.i./ha. Either a crop oil concentrate (1%) or non-ionic surfactant (0.25%) was added to the spray solution. The rates used depended on the compound and the combinations used in the test. The sprayer was calibrated to deliver the material in a volume of 93 1/ha through a TJ8001E spray nozzle at a pressure of 40 PSI.

After treatment, pots were returned to a greenhouse where they were watered and held in good growth conditions for two weeks. Plants were rated visually for defoliation effect at approximately 7-14 days after treatment. The defoliation effect is determined by counting the number of fully expanded leaves remaining on the plant and calculating the percent reduction from the number of fully expanded leaves on the plant at the time of spraying.

The results of the ratings taken at 14 days after treatment are summarized in Table 10

Test Example 4

Field trials were conducted on mature cotton grown in 36" rows. Treatments were applied when approximately 60% of the bolls were opened using a tractor mounted sprayer spraying 93L/ha. Compounds A-2 and A-5 were applied at 25, 50, 100 and 200 g a.i./ha with a non-ionic surfactant added at 0.25%. Evaluation for defoliation was made at 14 days after treatment.

The results are summarized in Table 11

Table 11

Test Example 5

Based on the results of Test Example 3, further utility of compound A-2 was examined by using lower rates of both compound A-2 and other commercial compounds. The results of this study are summarized in Table 12

Table 12

Test Example 6.

A field experiment was conducted with compound A-17 and other herbicides. Direct-seeded, field grown rice was treated at a spray volume of 94 L/ha. Compound A-17 was formulated as an emulsifiable concentrate and applied with 0.25 % non-ionic surfactant. All other compounds were used as the commercial formulations. Treatments were applied POST emergent, just prior to flooding of the rice paddies. Percent weed control was recorded at 7, 17 and 31 days after treatment. The data for 31 DAT is summarized in table 13. TABLE 13. Effect of compound A- 17 in combination with other herbicides for broadleaf weed control in direct seeded rice.

pennsylvanicum L.)

Addition of A-17 improved control of POLPY for all compounds, but especially for triclopyr and bensulfuron.

A further test with compound A-17 was done to examine grass control. Direct-seeded, field grown rice was treated at a spray volume of 94 L/ha. Compound A-17 was formulated as an emulsifiable concentrate and applied with 0.25 % non-ionic surfactant. All other compounds were used as the commercial formulations. Treatments were applied early-POST emergent. Percent weed control was recorded at 7, 14, 28 and 42 days after treatment. The data for 42 DAT is summarized in table 14.

TABLE 14. Effect of A-17 when combined with pendimethalin on control of grass weeds in direct seeded rice - 42 days after early POST emergent treatment.

(Note: Weed species abbreviations are ECHCG = Echinochloa crus-galli (L.) Beauv., LEFSS ^; Leptochloa sp.)

Combinations of A-17 with pendimethalin show greater control than either compound alone.

Claims

Claims 1. A herbicidal or plant growth regulatory composition comprising as the effective components A) at least one substituted benzene derivative of the formula I or its salt:

wherein X is halogen or nitro;

Y is hydrogen or halogen; W is oxygen or sulphur or imino;

Q is a heterocyclyl group of

Q5 Q6 Q7 Q8

Q10 Q11 Q12

Q13 Q14 Q15 Q16

Q17 Q18 Q19 Q20

Q21 Q22 Q23 Q24 wherein Ri is hydrogen, (C_1- )alkyl, halo(C_1-4)alkyl, (C_2-4)alkenyl, (C_2- )alkynyl, amino, (C_1-4)alkoxy(C_1-4)alkyl, acetyl, (C^alkoxycarbonylamino, (C_1-4)alkylcarbonylamino or (C _{\ ^}ι)alkoxycarbonyl; R₂ is (C_1-4)alkyl, halo(C_1- )alkyl, (C_1- )alkoxy or halo(C_1-4)alkoxy;

R₃ is hydrogen, halogen, nitro, amino, (C_1-4)alkylamino, halo(C_1-4)alkylamino, cyano or amide; R_\ and R₂ can take together with the atoms to which they are attached. They represent a 3-7 membered substituted or unsubstituted ring optionally, each of R4 and R₅ is oxygen, sulfur or imino; Q6, Q7, Q10, Q16 or Q17 may be unsaturated containing one or two double bonds in the

6-membered ring; and

B) at least one herbicidal compound selected from the group consisting of aryloxyalkanoic acids, aromatic carboxylic acids, ureas, triazines, anilides, hydroxybenzonitriles, quaternary ammonium salts, diphenyl ethers, triketones, aryloxyphenoxypropionic acids, oximes, sulfonylureas, imidazolinones, dinitroanilines, chloroacetanilides, oxyacetamides, thiocarbamates, amides, isoxazolidinones, quinoline carboxylic acids, isoxazoles, semicarbazones, chlorates and thiadiazoles, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds, urea compounds, tetraoxides and tetraoxosulfates.

2. The herbicidal or plant growth regulatory composition according to claim! , wherein the effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is halogen; Y is hydrogen or halogen; W is oxygen or sulphur;

R is an aryl or heteroaryl group in which these groups may be substituted with halogen, cyano, nitro, amino, carboxyl, (C_1- )alkyl, halo(Cι_-4)alkyl, (C_1- )alkylsilyl, (C_1-4)alkylcarbonyl, halo(C_1-4)alkylcarbonyl, (C_1-4)alkoxy, (Cι- )alkoxycarbonyl, halo(C_1- )alkoxy, halo(C_1- )alkoxycarbonyl, (C_1-4)alkylsulfonyl, halo(C_1-4)alkylsulfonyl, aryl, heteroaryl, or (C₃.₆)cycloalkyl;

Q is Ql, Q3, Q4, Q5, Q6, Q7, Q8, Q16 or Q17; wherein RI, R2, R3, R4 and R5 are as defined in claim 1; and Z is hydrogen; with a proviso that l-amino-3-[4-chloro-2-fluoro-5-(3-nifro-2-pyridyloxy)phenyl]-6-trifluoromethyl-l,2,3,4-tetrahyd ropyrimidine-2,4-dione is excluded; and

3. The herbicidal or plant growth regulatory composition according to claim 1, wherein the effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is halogen;

Y is hydrogen or halogen; W is oxygen or sulphur;

R is alkyl;

Q is Ql, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10 or Ql 1 ; wherein RI, R2, R3, R4 and R5 are as defined in claiml; and

Z is an alkyl or amino group in which these groups may be substituted with halogen, (C_1- )alkyl, (C_2- )alkenyl, (C_2- )alkynyl, amino, (C_3-6)cycloalkyl, hetero(C_3-6)cycloalkyl,

aryloxy-(C _1- )alkylcarbonyl, (C_2- )alkenylcarbonyl, (C_2- )alkynylcarbonyl, (C_3-6)cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C_1-4)alkoxycarbonyl,

(C3^)cycloalkyloxycarbonyl, benzyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl, aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl, (C _1- )alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl, (C_1-4)alkoxycarbonylcarbonyl or arylcarbonylcarbonyl; where any of these groups may be substituted with any of the functional groups represented by one or more of the following: halogen, cyano, nitro, amino, carboxyl, (C_1- )alkyl, halo(C_1-4)alkyl, (C_1- )alkylsilyl, (C_1- )alkylcarbonyl, halo(C_1-4)alkylcarbonyl, (C_1-4)alkoxy, (C_1-4)alkoxycarbonyl, halo(C_1-4)alkoxy, halo(Cι- )alkoxycarbonyl, (C_1- )alkylsulfonyl, halo(C_1-4)alkylsulfonyl, aryl, heteroaryl, or (C_3-6)cycloalkyl; and

4. The herbicidal or plant growth regulatory composition according to claiml, wherein the effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is halogen; Y is halogen; W is oxygen or sulphur;

R is an aryl or heteroaryl group in which these groups may be substituted with halogen, cyano, nitro, amino, carboxyl, (C_1-4)alkyl, halo(C_1- )alkyl, (C_1-4)alkylsilyl, (C_1-4)alkylcarbonyl,

(C_1-4)alkoxy, (C_1-4)alkoxycarbonyl, halo(C_1-4)alkoxy, halo(C_1-4)alkoxycarbonyl, (C_1-4)alkylsulfonyl, halo(C_1- )alkylsulfonyl, aryl, heteroaryl, or (C_3-6)cycloalkyl;

Q is Ql; RI is amino; R₂ is halo(C_1- )alkyl; R₃ is hydrogen; each of Ri and R₅ is oxygen; and Z is hydrogen; with a proviso that l-amino-3-[4-chloro-2-fluoro-5-(3-nifro-2-pyridyloxy)phenyl]-6-trifluoromethyl-l,2,3,4-tetrahyd ropyrimidine-2,4-dione is excluded; and

B) at least one herbicidal compound selected from the group consisting of aryloxyalkanoic acids, aromatic carboxylic acids, ureas, triazines, anilides, hydroxybenzonitriles, quaternary ammonium salts, diphenyl ethers, triketones, sulfonylureas, imidazolinones, dinitroanilines, chloroacetanilides, oxyacetamides, thiocarbamates, isoxazolidinones, quinoline carboxylic acids, isoxazoles, semicarbazones, chlorates and thiadiazoles, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds, urea compounds, tetraoxides and tetraoxosulfates.

5. The herbicidal or plant growth regulatory composition according to claiml, wherein the effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is halogen; Y is halogen; W is oxygen or sulphur; R is alkyl; Q is Ql; RI is (C_1-4)alkyl; R₂ is halo(C_1- )alkyl; R₃ is hydrogen; each of R* and R₅ is oxygen; and

Z is an alkyl or amino group in which these groups may be substituted with halogen, (C_1-4)alkyl, (C_2- )alkenyl, (C_2- )alkynyl, amino, (C_3-6)cycloalkyl, hetero(C_3-6)cycloalkyl, (C_1- )alkylsulfonyl, arylsulfonyl, benzyl, aryl, heteroaryl, (C_1- )alkylcarbonyl, aryloxy-(C_1- )alkylcarbonyl, (C_2- )alkenylcarbonyl, (C_2- )alkynylcarbonyl,

(C_3-6)cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C_1-4)alkoxycarbonyl, (C_M)alkylthiocarbonyl, (C_3-6)cycloalkyloxycarbonyl, benzyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl, aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl, (C i ^alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl, (C_1- )alkoxycarbonylcarbonyl or arylcarbonylcarbonyl; where any of these groups may be unsubstituted or substituted with any of the functional groups represented by one or more of the following: halogen, cyano, nitro, amino, carboxyl,

(C_1-4)alkoxy, (C_1-4)alkoxycarbonyl, halo(C_1-4)alkoxy, halo(C_1- )alkoxycarbonyl, (C_1-4)alkylsulfonyl, halo(C_1-4)alkylsulfonyl, aryl, heteroaryl, or (C_3-6)cycloalkyl; and

6. The herbicidal or plant growth regulatory composition according to claiml, wherein the effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is chlorine; Y is fluorine; W is oxygen; R is phenyl or pyrimidinyl in which these groups may be substituted with cyano or nitro; Q is Ql ; RI is amino; R₂ is halo(Cι-4)alkyl; R₃ is hydrogen; each of _t and R₅ is oxygen; and Z is hydrogen; and

B) at least one herbicidal compound selected from the group consisting of triazines, dinitroanilines, chloroacetanilides, oxyacetamides, chlorates and thiadiazoles, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds, urea compounds, tetraoxides and tetraoxosulfates.

7. The herbicidal or plant growth regulatory composition according to claiml, wherein the effective components are A) at least one substituted benzene derivative of the formula I or its salt; wherein X is chlorine; Y is fluorine; W is oxygen; R is alkyl; Q is Ql ; RI is (C_1- )alkyl; R₂ is halo(C_1-4)alkyl; R₃ is hydrogen; each of Rt and R₅ is oxygen; and Z is (C_1- )alkyoxycarbonyl-alkyl which may be substituted with halogen, arylcarbonyl-amino, aryloxy-(C_1-4)alkylcarbonyl-amino which may be substituted with nitro, or benzyloxycarbonyl-amino which may be substituted with nitro; and B) at least one herbicidal compound selected from the group consisting of triazines, dinitroanilines, chloroacetanilides, oxyacetamides, chlorates and thiadiazoles, or at least one plant growth regulatory compound selected from the group consisting of organic phosphorous compounds, urea compounds, tetraoxides and tetraoxosulfates.

8. The defoliation composition according to claiml, wherein the effective components are A) at least one substituted benzene derivative of the formula I or its salt; and

B) at least one herbicidal or plant growth regulatory compound selected from the group consisting of ethephon, dimethipin, tribufos, cyclanilide, thiadiazuron, paraquat sodium chlorate and AMADS as effective defoliants of cotton.

9. The desiccation composition according to claiml, wherein the effective components are A) at least one substituted benzene derivative of the formula I or its salt; and

B) at least one herbicidal or plant growth regulatory compound selected from the group consisting of ethephon, dimethipin, tribufos, cyclanilide, thiadiazuron, paraquat sodium chlorate, sulfuric acid and AMADS as effective desiccants of crop foliage.