JPS6219562A - Cyclohexane-1,3-dione derivative - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to an organic compound having biological activity, particularly an organic compound having herbicidal and plant growth regulating properties, a method for producing such a compound, and a method for producing such a compound. Intermediates useful in the manufacture of compounds, herbicidal compositions and methods of utilizing such compounds, and methods of utilizing such compositions.

[Conventional technology]

The use of certain cyclohexane-1,3-dione derivatives as grass herbicides is known in the art. For example, "Manual of Pesticides"
l) J (CR Worthing)
! i.

The Br1tlsh Crop Prot
@ctlonCounc i l ), 6th edition 197
9) is allozydi musodium (allozydi
m-sodlum), (methyl 3-(1-(allyloxyimino)tutyl)-4-hydroxy-6,6-
The present invention describes commercially known cyclohexane-1,3-dione derivatives and their use as herbicides for grasses. This compound is disclosed in Australian Patent No. 464,655 and its counterpart patents, such as British Patent No. 1,461,170 and US Patent No. 3,950,420.

5-(fi-substituted phenyl)cycloh-+? A wide variety of herbicidal compounds containing non-,3-diones are known in the art. For example, French Patent No. 2,518
, 990, as well as its corresponding published British patent application, i.e., 2,116.544.
(fet-substituted phenyl)cyclohexane-1,3-diones are described, and European Patent Application No. 085,52
No. 9 contains various 5-(substituted phenyl)cyclohexane-
1,3-diones and their herbicidal properties are described.

Hereinafter, Kinpaku [Structures of the Invention] Cyclohexane-1 having a 5-mesityl substituent, said substituent being substituted with a specific type of functionalized amino group,
It has now been discovered that a new group of 3-dione derivatives has an exceptionally high herbicidal activity on common grasses.

Therefore, the present invention is based on the following formula! = (During the ceremony.

Y is c, -C6 alkylsulfonyl, cl-C6)-roalkylsulfonyl, C2-C6 haloalkanoyl, R
5C0 and R5C8, where R5 is hydroxy, C1-C6 alkoxy, amino, C
selected from the group consisting of 1-C6 alkylamino and di(C,-C6 alkyl)amino, where z is hydrogen, halogen, C,-C4 alkyl, C2-C4 alkanoyl, sulfamoyl, C,-C4 alkylsulfamoyl, Ji(
C1-C4 alkyl) sulfamoyl, calgexy and trifluoroacetylamino; R1 is selected from the group consisting of hydrogen, an acyl group, and an inorganic or organic cation; R2 is c, -C6 alkyl, C2 -C6 alkenyl, C
2-C6 haloalkenyl, C,-C6 alkynyl.

and substituted C, -C6 alkyl (the alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl and substituted phenyl, and the benzene ring of the substituted phenyl is substituted with a group consisting of halogen and C1-06 alkyl) (substituted with 1 to 3 substituents selected from)
R3 is selected from the group consisting of C1-C6 alkyl, and R4 is selected from the group consisting of hydrogen, c, -C6 alkyl and (c, -C6 alkoxy) caryl). The present invention provides compounds that are expressed in a similar manner.

In the compound of formula I, when R1 in the formula is selected from acyl, the type of said acyl group is not narrowly critical. Without wishing to be bound by theory, it is believed that when R in the formula is acyl, said acyl group can be removed by hydrolysis in plants to yield the corresponding compound of formula 1 where R is hydrogen. Suitable acyl groups include:
Alkanoyl, e.g. C2-C6 alkanoyl; aroyl.

For example, benzoyl and substituted benzoyl, where the benzene ring is selected from the group consisting of halogen, nitro, cyano, C,-C6 alkyl, C-C haloalkyl, C1-C6 alkoxy and C,-C6 alkylthio.
Substituted with 3 substituents.

In the compound of the formula (2), when 81 in the formula is selected from inorganic or organic cations, the type of the cation is not narrowly critical and is not necessarily restricted, but
The cation is removed in the plant to form a compound of formula I in which R is hydrogen.
It is believed that the compound can be produced. Suitable inorganic cations include: alkali metal and alkaline earth metal ions, heavy metal ions such as transition metal ions, and ammonium ions. Suitable organic cations include the cation R'R'R8R-■, where R
, R, R and R are independently selected from the group consisting of: hydrogen: C1-C1° alkyl; substituted C, -C1
゜Alkyl, where the alkyl group is substituted with a substituent selected from the group consisting of hydroxy, halogen and C, -C, alkoxy; phenyl; benzyl; and substituted phenyl and substituted benzyl, where the benzene ring is substituted with a halogen , nitro, cyano, cl-C6 alkyl, c,
-C6 haloalkyl, C, -C6 alkoxy and C,
substituted with 1 to 3 substituents selected from the group consisting of -C6 alkyl group;

The compounds of the invention exist in two isomeric forms as follows: In the margin below, φ represents a group.

It is to be understood that when R1 is hydrogen, the compounds of the invention can exist in one of four tautomeric forms as follows: 1[a 11°1[c
lid where φ represents a group.

Preferred compounds of the invention include compounds of formula I in which each group has the following meaning: substituent Y is from trifluoroacetyl, trifluoromethanesulfonyl, alkoxycarnyl, carbamoyl and N-alkyla(thio)carbamoyl; selected from the group consisting of.

2 is selected from hydrogen, methyl, C2-C4 alkanoyl, halogen, sulfamoyl, dimethylsulfamoyl and trifluoroacetylamino; R1 is hydrogen, alkali metal cation, C2-C, alkanoyl, benzoyl and substituted benzoyl (where benzoyl the ring is substituted with 1 to 3 substituents selected from halogen, nitro and cyano), R is C1-C4 alkyl, C2-C4 alkenyl, C-
0furkynyl, C, -C4 haloalkyl, c2-'
selected from the group consisting of c4 haloalkenyl, R is selected from C1-C6 alkyl, and R4 is hydrogen.

Further preferred compounds of the invention include compounds of formula 1 in which each radical has the following meaning: Y is selected from the group consisting of trifluoroacetyl, trifluoromethanesulfonyl and N-alkylacarbamoyl, 2 is hydrogen, selected from methyl or acetyl, R1 selected from hydrogen and alkali metal cations, R2 selected from methyl, ethyl, n-propyl, allyl, propargyl and 3-chloroallyl, R3 selected from methyl, ethyl and n-propyl and R4 is hydrogen.

Examples of compounds encompassed by this invention are as follows: Particular examples of compounds of this invention include those detailed in Table 1 below. do.

Table 1 Compound number y zl
802CH3H 2C0NH2H 3C3NHCH2CH, H 4C0CF, H 5C0CF5COCH.

6 C0CC13H 7Co(CF2)2CF3 H 8C0NH(CH2)2CH,H 9802CF, H lo C0CF2CF3H 11C0NHCH,H The compounds of the present invention can be produced by various methods, and in another aspect, the present invention provides compounds of the formula A method for producing the compound (2) is provided.

Conveniently, the manufacturing method of the invention comprises four or five parts (
Section).

Part A is 5-arylcyclohexane-1,3- of the formula
Including the formation of dione derivatives. This reaction can be carried out in two steps as follows = (1) Preferably in the presence of a base, the aldehyde derivative of formula V is combined with acetone (R/
a) and an acetone derivative of formula (b) to form a ketone derivative of formula Mat or formula Mb, respectively, and the ketone derivative of (Ma) is reacted with malonic acid of formula (a), preferably in the presence of a base. or with an ester derivative of formula v
A ketone derivative of tb is reacted with a malonic ester derivative of formula b to form an intermediate of formula a″i! or l, respectively, which can be isolated or preferably Direct hydrolysis in the presence of 5-
Arylcyclohexane-1,3-dione derivatives can be produced.

01) Reacting an aldehyde derivative of formula (1) with an acetate ester of formula (C), preferably in the presence of a base, to produce a 2-aryl alkenoate derivative of formula Vlc, which is then reacted, preferably in the presence of a base. Reacting with an acetoacetate derivative of formula 1C below produces an intermediate of formula a, which can be isolated or directly hydrolyzed, preferably in the presence of an acid. , a 5-cyclohexane-1,3-dione derivative of formula (1) can be produced.

Part B includes acylating a compound of formula (1) to produce a 2-acylcyclohexane-1,3-dione derivative of formula (a).Alternatively, part B includes acylating a compound of formula and the formula XIa't7'c is Xlb
2-acylcyclohexane-1,3-dione derivatives, which can be hydrolyzed, preferably in the presence of an acid, to form the formula %. The acylation reaction can be carried out by reacting a cyclohexane-1,3-dione derivative of formula 1 or 2 with the following compounds: 1) Nikari's acid anhydride, the corresponding compound of formula Xv in the presence of an alkali metal salt of an acid or an alkoxide salt of formula X, where M is an alkali metal ion and R is C1-C6 alkyl; In the presence of the corresponding acid,
Preferably in the presence of a Lewis acid or strong protic acid catalyst, or l11) an alkali metal or alkaline earth metal hydride followed by a Niten acid anhydride or an acid halide, or lv) a Shikari acid anhydride. in the presence of a strong organic base such as 4-dimethylaminopyridine or imidazole.

Alternatively, this acylation can be carried out as follows: ■) A cyclohexane-1,3-dione derivative of formula ■ or formula ■ is reacted with the desired acid halide in the presence of a base to form the desired compound. and vi) reacting the intermediate of formula shoulder with a Lewis acid or strong protic acid catalyst or reacting the intermediate of vID 2 with a suitable strong organic base 1 e.g. 4
-React with dimethyl aminopyridine.

Part C involves reacting a compound of formula 1) (a) by trolation of an electrophilic aromatic to produce a compound of formula xb, the latter compound being subjected to reduction or N-acylation. It can be easily converted into a compound of formula Xc.

Part 1 encompasses the formation of compounds of the invention of formula (1), wherein R1 is hydrogen. This reaction is expressed by the formula
2-acylcyclohexane-1,3-dione of formula XIK by reacting with: l) an adult alkoxyamine derivative, or 11) a hydroxylamine An intermediate oxime derivative of formula XIK is formed and the intermediate oxime derivative of formula XIK is reacted with an alkylating agent of formula Xx, where L is a leaving group.

For example, the anions of chlorine, bromine, iodine, sulfuric acid, nitric acid, methyl sulfate, ethyl sulfate, tetrafluorophosphate, hexafluorophosphate, hexafluorophosphate, methanesulfonate, fluorosulfonate, fluoromethanesulfonate and trifluoromethanesulfonate. be.

Part E encompasses the formation of compounds of the invention of formula (1) where R is a substituent other than hydrogen.

Compounds of the invention of formula I, in which R1 forms an acyl derivative of a compound of formula (1), can be prepared from the corresponding compound of the invention of formula (2) by reaction with an acylating agent of XM. , in the formula is a leaving group, preferably hedan.

The compound of the formula (1) in which R1 is an inorganic or organic cation is a compound of the present invention (2) in which R is hydrogen, i.e., a compound of the formula It can be produced by reacting with For example, a compound of formula (1) in which R1 is an alkali metal can be prepared by reacting a suitable compound of formula (2) with a suitable alkali metal hydroxide or alkoxylade. Compounds of formula I in which R1 is a transition metal or an organic cation can likewise be prepared by reacting a suitable compound of formula 1 with a suitable transition metal salt or organic base. Alternatively, R is a transition metal i
Alternatively, a compound of formula (2) which is an organic cation can be prepared by reacting a suitable compound of formula (1) in which R1 is an alkali metal ion with a suitable transition metal salt or organic salt.

Therefore, in another aspect, the present invention provides a method for preparing a compound of formula (1) as defined above, which comprises the following steps: Al; react with xyamine derivative, or
Alternatively, the compound of the present invention of formula (1) is reacted with hydroxylamine and the oxime intermediate of formula (X) is alkylated with an alkylating agent of formula and optionally reacting a compound of the invention of formula XX with a compound of formula XXI, where is a leaving group to produce a compound of the invention of formula 1 .

Some of the intermediate compounds of formula XC are novel compounds, therefore, in another embodiment, the present invention provides
The present invention provides novel compounds and methods for their production.

The structural formula of the above compound is as follows: 1 m CH, C0CHsCH, C0CH2RCH, Co2R■
a ljb lVe below margin CHs CM.

v 'VlaR'
CH(Co2R) 2CH2(Co2R) 2■ILV
Eb CHC0C)tRCo R■C All white below Co2R Below margin below margin (R'C0) 20 RCo2M ROMM
Xm XIVRC02HR
C0hat XV XM H2NOR2R2L R' L XX XXI
A method of severely damaging or killing undesirable plants comprises applying a compound of the present invention to the undesirable plants or the growth environment of said plants.

In general, the formula! The compounds are selectively active against monocots, while dicots are relatively unaffected by the compounds of the invention at application rates that are severely damaging or lethal to other plant species. I don't accept it.

Then, in yet another aspect, the invention provides a method for controlling monocotyledonous weeds in cultivated crops, which method is sufficient to severely damage or kill said weeds; There is provided any method of applying a compound of formula (1) as defined above to said crop or the growth environment of said crop in an amount that is insufficient to substantially damage said crop.

The compound of formula ■ can be applied directly to the plant (post-emergent application) or applied to the soil before the plant germinates (pre-emergent application). However, these compounds are generally more effective when applied after germination of a single plant.

Although the compounds of formula I can be used on their own to inhibit plant growth, severely damage or kill plants, compositions consisting of a compound of the invention preferably mixed with a carrier consisting of a solid or liquid diluent used in the form of objects. Accordingly, in yet another aspect, the present invention provides a growth inhibiting compound comprising a compound of formula I as defined above and an inert carrier,
Provide a composition that damages or kills plants.

formula! Some of the compounds exhibit useful plant growth regulating activity. For example, the compounds of formula I are herbicides selectively active against wild grasses in crops of cultivated plants at certain application rates, but exhibit plant growth regulating effects in said crops.

Plant growth regulating effects can be expressed in many ways.

For example, apical bud dominance, stimulation of accessory axillary bud growth, stimulation of early flowering and seed formation, enhanced flowering and increased seed yield, thickening of the stem, stem shortening and tillering. a) Plant growth regulating effects exhibited by the chemical compound of the present invention include, for example, the development of burrs and stem shortening in crops such as wheat and barley.

Accordingly, in yet another aspect, the present invention provides a method for regulating the growth of plants, which comprises applying to a plant, plant, seedling or growth environment of the plant an effective amount of a compound of the formula summer defined above. provide.

To carry out the method of controlling the growth of plants according to the invention, a compound of formula I can be applied directly to the plant (post-emergent application) or to the soil before the seeds germinate (pre-germinated application). Can be done.

Although the compounds of Part I can be used on their own for the regulation of plant growth, they are generally used in the form of compositions comprising a compound of the invention mixed with a carrier, preferably a solid or liquid diluent. be done. Therefore, in yet another aspect, the present invention relates to the formula ! defined above. A plant growth regulating composition comprising a compound of the present invention and an inert carrier is provided.

The compositions of the invention can be in solid, liquid or paste form. Compositions include both dilute compositions that are ready for use and thick compositions that may require dilution before use. The concentration of active ingredient in the compositions of the invention therefore depends on the type of formulation and whether the composition is ready for use, for example whether it is a dust formulation or an aqueous emulsion, or whether the formulation is It will vary depending on whether it is a concentrate, for example an emulsifiable concentrate or a wettable powder suitable for dilution before use. Generally, the compositions of the present invention range from ippm to 99″ff
Consisting of i amount of active ingredient.

Solid compositions can be in the form of powders, dusts, pellets, grains and granières, in which the active ingredient is mixed with a solid diluent. Powders and dusts can be prepared by mixing or grinding the active ingredient with a solid carrier to give a finely divided composition. Granules, granules and pellets are produced by binding the active ingredient to a solid carrier, for example by coating or impregnating a preformed granular solid carrier with the active ingredient, or by agglomeration techniques. Can be prepared.

can.

Solid carriers include: mineral earths and clays such as kaolin, bentonite, diatomaceous earth, Aller's earth, Attaelay, diatomaceous earth, bolus, loess, talc, chalk, dolomite,
Limestone, lime, calcium carbonate, gypsum, calcium sulfate, /4 ylophyllite, silicic acid, silicates and silica gels; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea: natural products of vegetable origin, such as grain flours; (m@al) and powder (f
lour), bark flour, wood flour, walnut shell flour and cellulose powder; and synthetic/IJ mammaries such as ground or powdered plastics and resins.

Alternatively, the solid composition can be a dispersible or wettable dust, powder, granule or granule, in which the active ingredient and a solid carrier are combined with one another, which acts as a wetting agent, emulsifying agent and/or dispersing agent. or in combination with two or more surfactants to promote dispersion of the active ingredient in the liquid.

Examples of surfactants include cationic, anionic, and nonionic. Cationic surfactants include quaternary ammonium compounds such as long chain alkyl ammonium salts such as cetyltrimethylammonium bromide. Anionic surfactants include alkali metal, alkaline earth metal and ammonium salts of disoaps or fatty acids; alkali metal, alkaline earth metal and ammonium salts of lignin sulfonic acids; Salts of alkali metals, alkaline earth metals and ammonium, for example salts of naphthalenesulfonic acid, such as butylnaphthalenesulfonic acid, di- and tri-isopropylnaphthalenesulfonic acid, salts of sulfonated naphthalenes and condensation products of naphthalene derivatives with formaldehyde. , salts of sulfonated naphthalenes and condensation products of naphthalene derivatives with phenol and formaldehyde and alkylarylbenzenesulfonic acids,
For example, salts of dodecylbenzenesulfonic acid; alkali metal, alkaline earth metal and ammonium salts of sulfuric acid or alkyl sulfates, such as lauryl sulfate, and monoesters of sulfuric acid and aliphatic alkyl ethers. Non-ionic surfactants include: condensation products of ethylene oxide with phenols and alkylphenols, such as inoctylphenol, octylphenol and nonylphenol; condensation products of ethylene oxide with castor oil: long-chain fatty acids and hexitols. Partial esters derived from anhydrides, such as sorbitan monooleate and their condensation products with ethylene oxide; ethylene oxide/propylene oxide block]-rimers; lauryl al]-polygly]-lether acetals; and lecithin.

The liquid composition may optionally contain wetting agents, emulsifying agents and/or
Alternatively, it may consist of a solution or dispersion of the active ingredient in a liquid carrier containing one or more surfactants acting as dispersants. Liquid carriers include: Water: Mineral oil fractions, such as kerosene, solvent naphtha, petroleum, coal tar oil and aromatic petroleum fractions: Aliphatic, cycloaliphatic and aromatic hydrocarbons. ,for example,/
weighing compounds, cyclohexane, toluene, xylene, tetrahydronaphthalene and alkylated naphthalenes; al]-ols, such as methanol, ethanol, chromols, isoglols/ols, tutanol, cyclohexanol and prepylene glycols: ketones; For example, cyclohexanone and isophorone: and strongly polar organic solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and sulfolane.

Preferred liquid compositions consist of aqueous suspensions, dispersions or emulsions of the active ingredients suitable for application by spraying, atomizing and trickling.

Such aqueous compositions are generally prepared by mixing the concentrated composition with water. Suitable concentrated compositions include emulsion concentrates, pastes, oil dispersions, aqueous suspensions, and wettable powders. Concentrates are usually required to withstand long-term storage and, after such storage, are diluted with water to form an aqueous preparation that can be applied through conventional spray equipment. so that it stays homogeneous for enough time. For good thick items, it is convenient to use 10 to 99 lids.
Preferably it contains 10-60% by weight of active ingredient.

The emulsion or emulsifiable concentrate conveniently contains one or two
It is prepared by dissolving the active ingredient in an organic solvent containing one or more surfactants and optionally an oil.

Oil dispersions contain an active ingredient, a hydrocarbon oil, and one or more
It can be prepared by grinding more than one type of surfactant.

The aqueous suspension concentrate conveniently contains the active agent and preferably at least IF'! A mixture of suspending agents can be prepared by tail milling.

Suitable suspending agents include dihydrophilic colloids, such as pri(N-vinylpyrrolidone), sodium carboxymethylcellulose and vegetable combs, acacia and tragaca/), co''A: Hydrated colloidal mineral silicates such as montmorillonite, paypride (b@1d@111t), nontronite, hectoride, gardevoir, sauconite and bentonite; other cellulose derivatives; Wettable powder concentrates conveniently contain the active ingredient, 111i or more surfactants, 1m or more solid carriers and optionally IgI or more than one surfactant. It can be prepared by combining the suspending agent and milling the mixture to form a powder having the desired particle size.

Aqueous suspensions, dispersions or emulsions can be prepared from concentrated compositions by mixing the concentrated composition with water optionally containing a surface-active ingredient and/or an oil.

It should be noted that the compounds of the invention of formula (1) where R1 is hydrogen are acidic. The compounds of formula I can therefore be formulated and applied as salts with organic or inorganic bases. When formulating and using a compound of formula (1) in the form of a salt, the salt itself or the compound of formula (1) where R is an inorganic or organic cation can be used in the formulation, or where R is hydrogen. The salt can be generated in situ by using a compound of formula (1) in the formulation and using a suitable inorganic or organic base.

The method of applying the compositions of the invention will depend, to a large extent, on the type of composition used and the equipment with which it is applied. Solid compositions may be applied by dusting or other suitable means for dispersing the solids. Liquid compositions may be applied by spraying, atomizing, trickling, introduction into irrigation water, or other suitable means of scattering or dispersing bulk liquid.

The rate of application of the compounds of the invention depends on a number of factors, e.g.
The compound selected for use, the body of the plant whose growth is to be inhibited (
id@nt1ty) will depend on the formulation selected for use and whether the compound is applied for foliar or root absorption; however, as a general guideline:
Application rates of 5 to 20 Kf/ha are suitable, but 0.01 to 5.09 Kf/ha may be preferred.

Compositions of the invention may include, in addition to one or more compounds of the invention, one or more compounds that are not of the invention but have biological activity.

For example, as indicated above, the compounds of the present invention are generally substantially active against monocotyledonous or grass species as well as dicotyledonous or broad-leaved foods. As a result, in some applications, the use of the compounds of the invention alone as herbicides may not be sufficient to protect the crop. Accordingly, in yet another aspect, the invention provides:
There is provided a herbicidal composition comprising a mixture of at least one compound of formula (1) as defined above and at least one other herbicide.

The other herbicide can be any herbicide that does not have Formula 1. It will generally be a herbicide with complementary action. For example, one preferred class is mixtures containing herbicides that are active against broadleaf weeds. The second category is mixtures containing contact herbicides.

Examples of useful complementary herbicides include: A, benzo-2,113-thiadiazin-4-one-2
, 2-dioxide, such as 3-isopropylpenzo2.1.3-thiadiazin-4-one-2,2-dioxide (common group bentazon)
:B, hormonal herbicides and especially phenoxyalkanoic acids, such as 4-chloro-methylphenoxyacetic acid (commonly MCPA), 2-(2,4-dichlorophenoxy)propionic acid [commonly diehlo
rprop) ], 2,4-dichlorophenoxyacetic acid (common group 2,4-D), 2,4.5-trichlorophenoxyacetic acid (common group 2,4,5-T), 4-(4-chloro-2 -methylphenoxy)butyric acid (common group MCPB)
, 4-(2,4-dichlorophenoxy)butyric acid (usually group 2
．． 4-DB), 2-(4-chloro-2-methylphenoxy) f ropionic acid [commonly group mecodelop (m@copro
p) ], said derivatives thereof (e.g. salts, esters, amides, etc.); 0.3-[4-(4-halophenoxy]phenyl]-1
, 1-dialkyl urea, for example 3-1:4-(4-chlorophenoxy]phenyl]-1,l-dimethylurea [
Ordinary group chloroxuron (ebloroxuron)
): D. dinitrophenols and their derivatives (e.g. acetate), e.g. 2-methyl-4
, 6-sinitrophenol (ta name DNOC), 2-
tart-butyl-4,6-sinitrophenol [commonly dinoterb], 2-gsc-butyl-
4,6-sinitrophenol [commonly radical dinosef (din
oaeb)) and its ester dinocepacetate; E, dinitroaniline herbicides, such as N', N'-
Diethyl-2,6-sinitro 4-trifluoromethyl-m-phenylenediamine (fa name resinitramine d
initramims )], ]2,6-sinitro N,N-dipropyl 4-trifluoromethylaniline [
common radical trifluralin (trifluralim)
) and 4-methylsulfonyl-2,6-sinitro N
, N-dipropylaniline (common name ntralin): F, phenylurea herbicides, such as N'-(3,4-cyclophenyl)-N,N-dimethylurea (common name diuron) and N,N-dimethyl-N'-(3-()lifluoromethyl)phenyl]urea [common group fluorometuron
) ) :G, phenylcarpamoyl-Φdiphenylcarbamate, e.g. % 3-((methylsulfonyl)7
Mi/) Phenyl (3-methylphenyl) carbamate [
common group phenmedlpham
)) and 3-[(ethoxycarbunyl)aminocophenylphenylcarbamate [common name desmedipham (d*sm@dipham): l:H,2-phenylpyridazin-3-ones, e.g. 5-amino-4-
Chloro-2-phenylpyridazin-3-one [common disease 2
pyrazon)'.

■, 2-sil herbicides, such as 3-cyclohexyl-5
, 6-) Rimethylene U2cil [Common disease Renacil (1na)
eil )), 5-promo 3-1ec-butyl-6
-Methyluracil (common name bromaa)
)) and 3-tart-butyl-5-chloro-6-methyluracil [common name terpacil (t@rb
ae11)):J,)Riazine herbicides, e.g. 2-chloro-4-ethylamino-6-(1t3#5))Riazine [common disease atrazine (atrazlne)), 2 -chloro-4,
6-di(etheramino)-1,3,5-)riazine [common disease simazim@), 2-azido-4-(1to-propylamino)-6-methylthio-
1,3,5-)Riazine [Common disease Adiproptia (a
zlproptyne)): 1-alkoxy-2-alkyl°-3-phenylurea herbicides, such as 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea [common name: 1inuro
n) ), 3-(4-chlorophenyl)-1-methoxy-1-methylurea [monolinuron] and 3-(4-promo-4-'lorophenyl)-1-methoxy-1-methylurea [ Common disease chlorobromeron (chlorobrobro)
mron)); L, hyridine herbicides, such as 3,6-dichloropicolinic acid [common disease cloviralid (
elopyralid)) and 4-amino-3,5,
6-) Dichloropicolinic acid [common name: picloram (pic)
loram)):M' 1t2t4-) riazine-5
-one herbicides, such as 4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-)riazin-5-one (common disease metamidron (matanxitr)
on)) and 4-amino-6-t@rt-butyl-4,5-dihydro-3-methylthio-1,3,4-)
Riazin-5-one [common disease metribuzin (m@tri)
busln ) ) : N, benzoic acid herbicide, e.g. %
2t3,6-)U chlorobenzoic acid (common disease 2, 3
, 6-TEA), 3,6-sochloromethoxybenzoic acid [common name dicmmbm] and] 3
-amino-2,5-dichlorobenzoic acid common disease chlorampen (ehloramb@n)]: 0. Anilide herbicides, such as N-toximetal-α-chloro-27,6/-diethylacetanilide [common name butmahlor] ), the corresponding N-methoxy compound [alachlor (alaeh
lor), the corresponding N-inbromol compound [common name: propaehlor], and 3/, 4
/-dichloroglopionanilide (common name glopar)
propantl)) e.

゛　　　　　　　　.

P, dihalobenzonitrile herbicide 2 For example, 2゜6-cyclobenzonitrile [common disease dichlobenil (dich
lobenil)), 3,5-dibromo-4-hydroxybenzonitrile (- is the joint name bromoxynil (b
romoxynil) ) and 3°5-short-
4-Hydroxybenzonitrile (common name: 1oxynil): Q, haloalkanoic acid herbicides, such as 2,2-dichloroglobio/acid (common name: dalapon), trichloroacetic acid (common name: dalapon);
OA) and salts thereof; space below λ diphenyl ether removal agent, for example, 4-nitrophenyl 2-nitro-4-) fluoromethyl phenyl ether C common name 7, t.

fluorodifsn), methyl 5-(2,4-dichlorophenoxy)-2-nitropenzoate (common name bifenox), 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy) ) Benzoic acid and 2-chloro-4-trifluoromethylphenyl 3
-Ethoxy-4-nitrophenyl ether; S,N-(heteroarylaminocar♂yl)henzensulfonamide, sidelight Id, 2-rio.

-N-((4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocardenyl]benzenesulfonamide (1I common name DPX 4189): T, aryloxyphenoxyzolobionate herbicide , for example, butyl 2-(4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionate (common name fluazifop 17') and methyl 2-(4-(2,5-dichlorophenoxy) Phenoxy] blowonate [common name: diclof! (dia
lofop)]: and 011 herbicides, such as N,N-dimethyldiphenylacetamide [common name cifuenamide (dfph@namjd)], N-(1-naphthyl]phthalamic acid [common name napti
lam)) and 3-amino-1,2,4-)riazole O Useful contact herbicides include: V, bipyridine herbicides, for example, where the active entity is 1,1'-dimethyl -4,4'-diviridylium ion [common name paraquat] and the active entity are 1
, 1'-ethylene-2,2'-diviridylium ion [
Common name dlquat]: organic arsenic herbicides, such as monosodium methane arsonate (common name MSMA): and X-amino acid herbicides, such as N-(phosphonomethyl)glycine [
Glyphosate (common name: glyphosat@) and its salts and esters.

〔Example〕

The invention will be further illustrated by the following examples. Note that the present invention is not limited to these Examples.

Example 1:) Fuming nitric acid (2,17mj), glacial acetic acid (1,98d)
and acetic anhydride (1,c+4*).
2-propionyl-3-hydroxy-5-mesitylcyclohex-2-en-1-one (1
01,34,9 mmol) dropwise at 5°C. Stirring was continued for 1 hour at 5°C, then 2 hours at 20°C and 10 minutes at 50°C.

The mixture was then cooled and poured into ice water.

This aqueous solution was extracted with methylene chloride. The organic layer was washed with water, saturated bicarbonate solution, and then more water;
Dry over anhydrous sodium sulfate and concentrate under reduced pressure.
2-Propionyl-3-hydroxy-5-(3-nitro-2,4,6-trimethylphenyl)cyclohexy-2
-en-neon was obtained as a pale yellow solid (9.5
9p, 83 yen). This compound was characterized by t-proton magnetic resonance spectroscopy (CDC2I: δ, ppm)
: 1.15(3H,t):2.18(3I(,@):
2.24 (3H, s): 2.38 (3H, a,): 2.
4-4.1 (7H, tn); 6.88 (IH, l):
18.20 (In 2 meals).

! 501kf) water-based: t-fi)-ru (350m
l) Medium (D2-propionyl-3-hydroxy-5
-(3-two-row 2.4.6-)! J methylphenyl)
Cyclohexy-2-en-1-one (9,59p, 28
．． 9 mmol) and sodium hydroxide (1,10,P
.

Sodium dithionite (27.74f, 159 mmol) was added over 30 minutes to a refluxing solution of 27.5 mmol]. Reflux was continued for 1 hour. This hot mixture t-
Filter, neutralize with dilute hydrochloric acid and extract with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to yield the crude 2-propionyl-3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl]cyclohexy-2 (3.0), 345 g), which was characterized by proton magnetic resonance spectroscopy (
coct5: δ, ppm): 1.17 (3H
v t): 2.12 (3H, s): 2.20 (3H, s
): 2.25 (3He l ): 2.3-4.2
(7Hem): 6.72 (IHLS).

iiD 2-propionyl-3-hydroxy-5-(3-amino-2,4,6- in methylene chloride (1(ld))
To a stirred solution of [trimethylphenyl]cyclohex-2-en-1-one (1,OF, 3.3 mmol) was added t-pyridine (0.53 sd, 6.6 mmol), followed by methanesulfonyl chloride (0, 521111.6.6 mmol) was added. Stirring was continued for 8 hours at 20°C. The organic layer was washed with water, dilute hydrochloric acid, and more water, dried over anhydrous magnesium sulfate, and subjected to vacuum mast to obtain the crude product gold. This crude material was purified by column chromatography on silica gel (eluting with an increasing gradient of methanol in methylene chloride) to produce 2-propionyl-3-hydroxy-5-(3-methylsulfonamide-2,4,
6-trimethylphenyl)cyclohex-2-ene-1
-one was obtained as a yellow waxy solid (0.6P, 5
01° This compound was characterized by proton magnetic resonance spectroscopy (CDCj3:δ, PPrn): 1.17 (3
HIt): 2.35 (6H.

a): 2.46 (3H#s): 3-0 (3H-m):
2.4-4.1 (7H, m): 6.78 (IH, i):
6.89 (IH, s): 18.15 (1B, brs).

i) 02-Globionyl-3-hydroxy- in ethanol (25Wt) and methylene chloride (25m)
5-(3-methylsulfonamido-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0
, 58), 1.53 mmol] were added sodium acetate (0.19 p, 2.29 mmol) and ethoxyamine hydrochloride (0.227, 2.29 mmol) at 20 °C. Stirring was continued for an hour. The solvent was removed under reduced pressure and the residue was partitioned between chloroform and water.
The organic layer was washed with water, dried over anhydrous magnesium sulfate,
Then, when concentrated under reduced pressure, 2-[1-(ethoxyimino]
Propyl]hydroxy-5-[3-(methylsulfonamido)-2t''!t6-trimethylphenyl]cyclohexy-2-mono-1-one was obtained as a brown color (0
．． 27p, 42%). This compound was characterized by proton magnetic resonance spectroscopy. The spectroscopic data are listed in Table 2.

Example 2 1] 2-propionyl-3 in ethanol (5 mg)
-Hydroxy-5-(3-amino-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (1
, OP% 3.32 mmol) was added ethyl isothiocyanate (0,357,3,98 mmol). Stirring was continued for 4 days at 20°C.

Dilute acid and methylene chloride were added. The organic layer was washed with water, dried over magnesium sulfate, and concentrated. The crude product was purified by chromatography on silica dal (eluting with an increasing gradient of methanol in methylene chloride) to yield 2-propionyl-3-hydroxy-5-(3
-Ethylthioureido-2,4,6-trimethylphenyl)cyclohex-2-en-1-one was obtained as an oil (0.4P, 33%), this compound was characterized by proton magnetic resonance spectroscopy. (coct, , δ%
ppm): 1.12 (6H, t): 2.18 (3H, s
)': 2.28 (3H, m); 2.39 (3H, a):
2.4-4.2 (9H#m): 5.4 (IHabrs)
:6.29(IHtm):8.34(IHabrs)
.

ii) 2-(1-(ethoxyimino)propyl'')
-3-hydroxy-5-(3-ethylthioureido-2
,4,6-trimethylphenyl)cyclohex-2-en-1-one from the above compound in Example 1, part (iv).
). This compound was characterized by proton magnetic resonance spectroscopy, and the spectroscopic data are listed in Table 2.

Margin below Example 3 1) 2-Propionyl-3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)cyclohexy-2 in acetic acid (91nl) and water (3,2TrLl)
A solution of -en-l-one (1.0 g, 3.32 mmol) was added with potassium cyanate (0.54 p,
6.66 mmol) was carefully added. Stirring was continued for 1 hour and then left for 15 hours. Water and ethyl acetate were added. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give 2-zolobionyl-3-hydroxy-5-(3-ureido-2,4
,6-trimethylphenyl)cyclohex-2-ene-
1-on is obtained as a brown feeling and 7'? (0.96g, 8
4-). This compound was characterized by proton magnetic resonance spectroscopy (CDC23, δ, ppm): 1.1
1 (3H, t): 2.20 (3H, s): 2.32 (6
H.

s): 2.4-4.1 (7H*m): 5.12 (2H*
br+s): 6.82 (IHt a) near, 25 (IH
tbrs).

1i) 2-(1-(ethoxyimino)7propyl]-3
-Hydroxy-5-(3-ureido-2,4°6-trimethylphenyl)cyclohex-2-en-1-one was prepared from the corresponding trione as described in Example 1, Part 4. . This compound was characterized by proton magnetic resonance spectroscopy, and the spectroscopic data are presented in Table 2.
Describe it in

Example 4 1) 2-Propionyl-3-hydroxy-5-(3-amino-214es) in trifluoroacetic anhydride (2G)
-) cyclohex-2-ene-1
-one (o, B, 1.66 mmol) at 20°C.
The mixture was stirred for 48 hours. Water was then added and the aqueous layer was extracted with chloroform. Wash the organic layer thoroughly with water,
Dry with sodium sulfate and concentrate. The crude product was purified by chromatography on silica gel (eluting with an increasing gradient of ethyl acetate in dichloromethane) to give 2-propionyl-3-hydroxy-5-(3
-trifluoroacetamide-2゜4,6-) +
7methylphenyl)cyclohex-2-en-1-one was obtained as a yellow solid (0.29.f, 44%).

This compound was characterized by proton magnetic resonance spectroscopy (CDCts tδ.

ppm): 1.16 (3H, t), 2.16 (3H,
s): 2-21 (3He s): 2-26 (
3H, s): 2.4-4.1 (7H*m)
: 6.89 (IH, tr) : 850 (LH, a
): 18.15 (IH, Seal).

1i) 2-(1-(ethoxyimino)f-ropyl]-3-
Hydroxy-5-(3-1 lifluoroacetamide-2
,4,6-trimethylphenyl)cyclohex-2-en-1-ion from the above precursors in Example 1, Part 4.
Manufactured as described above. This compound was characterized by proton magnetic resonance spectroscopy, and the spectroscopic data are listed in Table 2.

Example 5 (5) 1) 2-propionyl-3-hydroxy-5-[3
-acetyl-5-nitro-2,4,6-trimethylphenyl]cyclohex-2-en-1-onef,2-fropionyl-3-hydroxy-5-[3-acetyl-2,
4,6-trimethylphenyl]cyclohex-2-en-1-onkara was prepared. This compound was characterized by proton magnetic resonance spectroscopy (CDCl2.δ-ppm
): 1.14 (3H, t): 2.08 (3H, Peng)
: 2.29 (6H.

s): 2.46 (3H, s): 3.03 (2Hs q)
:2.4-4.1(5H,m);18.00(IH,s
).

11) 2-propionyl-3 in methanol (80d)
-Hydroxy-5-[3-acetyl-5--41:! −
214# 6-trimethylphenyl]cyclohexy-2
A solution of -en-1-one (4,2 g, 11,3 mmol) and sodium methoxide (0,619,11,3 mmol) was prepared at atmospheric pressure on 10% noeradium on charcoal (0,3 g). Hydrogenated in the presence of After hydrogen uptake ceased, the solution was neutralized and methanol was removed under reduced pressure.

The residue was partitioned between water and methylene chloride.

The organic layer was washed with water, dried over anhydrous sulfuric acid and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (eluting with an increasing gradient of methanol in methylene chloride) to yield 2-propionyl-3-hydroxy-5-(3-acetyl-5-amino-2,4 ,6-trimethylphenyl)cyclohexy-2
-en-1-one was obtained as a reddish-brown color (3.28
p, 85ch). This compound was characterized by proton magnetic resonance spectroscopy (CDct, *δe ppm)
: 1.18 (3H, t): 2.0 (3H, a): 2.
12 (3H.

s): 2.18 (3H, s): 2.40 (3H, s):
2.4-4.1 (5H, rn): 3.07 (2H, ct
):3.6(2H,bri):18.05(IH*b
rs).

111) 2-Propionyl-3-hydroxy-5-(3-acetyl-5-
A solution of amino-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.46 g, 1.34 mmol) was stirred at 20<0>C for 1 hour. Then water and ether were added.

The organic layer was washed thoroughly with water, once with saturated bicarbonate (IJ), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was chromatographed on silica gel (eluting with 10-ethyl acetate in methylene chloride).
When purified by
-en-1-one was obtained as a brown solid (0.37
g, 63ch). This compound was characterized by proton magnetic resonance spectroscopy (coct, , δ, ppm):
1.12 (3H, t): 1.73 (3H, s): 2.
22 (3H, @): 2.26 (3H, s): 2.46 (
3H, s): 2.4-4.1 (5H, m): 3.08 (
2H,q): 9-29 (IH,s):
1 B, 33 (IH, @).

1V) 2-(1-(ethoxyimino)propyl]-3-
Hydroxy-5-[3-acetyl-5-trifluoroacetamido-2,4,6-trimethylphenyl]cyclohex-2-en-1-sperm from the corresponding compound,
Prepared as detailed in Example 1, part ivl. The compound was characterized by proton magnetic resonance spectroscopy. The spectroscopic data are listed in Table 2.

Example 6 Compounds &8 and 11 were prepared following a procedure similar to that described in Example 2 and starting from the appropriate incyanate. These compounds were characterized by their behavior on thin layer chromatography and proton magnetic resonance spectroscopy. The spectroscopic data are summarized in Table 2 of Example 8 below.

Example 7 Compounds &6, 7, 9 and 10 were prepared following a procedure similar to that described in Example 4 and starting from the appropriate acyl and sulfonic anhydride. These compounds were characterized by proton magnetic resonance spectroscopy and thin layer chromatographic behavior. The spectroscopic data are summarized in Table 2 of Example 8 below.

Example 8 Most of the compounds of the invention are obtained as oils and can be characterized and identified by nuclear magnetic resonance spectroscopy. For convenience, proton nuclear magnetic resonance (PMR) spectroscopy data are listed in Table 2 below.

Margin table 2 below 1 Brown emotion 1.18 (3H, t): 1.33 (3
H, t): 2.35 (6H, s): 2.44 (3H, s
): 3.04 (3H, a): 2.4-4.2 (7H, m
):4.13(2H,q):6.85(IH,s):6
．． 92 (IH, s).

Table 2 (Continued) Example 9 This non-limiting example illustrates the preparation of formulations of the invention.

&) 1 teric of 7% v/v emulsifiable concentrate compound A2.
)'N13 and 3% v/v of 1 Kemmato (Kem
mat) '5C15B to form an emulsifiable concentrate. This can be diluted with water to the required concentration to prepare an aqueous emulsion that can be applied by spraying.

[“T@ric” is a trademark and “
Terlc”N13 is an ethoxylation product of nonylphenol;
)” is a trademark, and “Kemmat” is a trademark.
"5C15B is a formulation of calcium dodecylbenzene sulfonate." b) Aqueous suspension Compound 8 (5 parts by weight) and "Dyap
ol)' P T (1 part by weight) is
ric) was added to an aqueous solution of N8 (94 parts by weight) and the mixture was sol-milled to form an aqueous suspension. It can be diluted with water to the required concentration to prepare an aqueous suspension that can be applied by spraying.

[“Dyapol” is a trademark and “Dyapol” PT is an anionic suspending agent; “Torie” N8 is an ethoxylation product of nonylphenol. ]C)
Emulsifiable concentrate compound A2 (10 parts by weight), 1 Terie
)”N15 (5 parts by weight) and “Kemmato (K@mma
t) "5C15B (5 parts by weight) was added to "Tsurupets (5o
lv*sso)' 150 (80 parts by weight) to form an emulsifiable concentrate. It can be diluted with water to the required concentration to prepare an aqueous emulsion that can be applied by spraying.

[1 Tsurupettsu (Sotma・110)” is a trademark, and “Tsurupetsutsu (8o1ma・sso) '″1
50 is a high boiling aromatic petroleum fraction. ] The following remainder d) Dispersible powder compound AI (10 parts by weight), "Mat*x
il) 'DA/AC (3 parts by weight), 'Asrozol' OT/B (1 part by weight) and Kaolin 298 (86 parts by weight) were blended and then milled to a particle size of less than 50 microns. A powder composition having the following was produced.
”' DA/AC is a trademark,
Mat@xl 1), 'DA/AC is the "sodium salt" of naphthalene sulfonic acid/formaldehyde condensate; "Aerozol"
is a trademark, and “A.rozol” is a trademark.
OT/B is a blend of dioctyl ester of sodium sulfosuccinic acid.
0 parts by weight) and .9 irophyllite (80 parts by weight) were well blended and then ground in a hammer mill to produce a powder with a particle size as small as 200 microns.

Emulsifiable concentrates and/or suspensions of compounds of the invention are prepared essentially as described in a), b) or C) above, optionally with surfactants and/or oils. to give an aqueous composition of the required concentration. This was used in the evaluation of pre- and post-emergent herbicidal activity of compounds as described in Examples 10-12.

Example 10 The pre-emergence herbicidal activity of compounds of the invention formulated as described in Example 9 was evaluated by the following procedure: Seeds of the species to be tested were placed in seed boxes and placed in nine soils. on 21
sowed to a depth of The monocots and dicots were sown in separate boxes and after sowing the two boxes were sprayed with the required amount of the composition of the invention.

Two replicate seed boxes were prepared in the same way but were not sprayed with the composition of the invention and were used for comparison purposes. All boxes were placed in a greenhouse and lightly watered with overhead spray to initiate germination, followed by sub-irrigation as needed to maintain optimal plant growth. After three weeks, the boxes were removed from the greenhouse and the effects of the treatment were visually evaluated. The results are listed in Table 3. In this Table 3, plant damage was graded on a scale of O to 5. 0FiO~
1 represents 10% damage, 1 represents 11-30% damage, 2 represents 31-60% damage, 3 represents 61-80% damage.
4 represents damage from 81 to 99 inches;
5 represents 1001% kill. Dash (-)
means that the experiment was not performed.

The names of the test plants are as follows: 恰 Wheat (wh・at) Or Oat (Wild 0ats) Rg
Rye grass (Rh@grass) Jm Japanese barnyard grass (Jap)
anese m1ll@t )B Barley
ey ) P Entou (Peas) Ip Mexico Ska Sonia (IpOlnlSIL) M
s Power 2 China (Mustard) Sf Himawari (5unf lower) Table 3 1 1.0 2553500002 1.0
3543200003 1.0 5555
500003 0.25 45442---4
1.0 5555500004 0.25
5 5 5 5 5 - - - -5 1.0
5555500005 0.25 555
55----6 1.0 55554055
47 1.0 2555100008 1.0
5555510118 0.25 555
55----9 1.0 555-542019
0.25 355-5---10 1.
0 5 5 5 5 5 0 0 0 010
0.25 5 4 5 5 5 - - - -1
1 1.0 5 5 5 5 5 0 0 0
011 0.25 5 5 5 5 5 - -
- Example 11 The post-emergence herbicidal activity of compounds of the invention formulated as described in Example 9 was evaluated by the following procedure: Seeds of the species to be tested were placed in soil contained in seed boxes. It was sown to the depth of two countries. Monocots and dicots were sown in separate boxes in replicate experiments. Four seed boxes were placed in the greenhouse and lightly watered with overhead spray to initiate germination, followed by sub-irrigation as needed to maintain optimal plant growth. Approximately 10-12 plants
．． After growing to a height of 55R, one box each of monocots and dicots were removed from the greenhouse and sprayed with the required amount of the composition of the invention. After spraying, place the box in the greenhouse for another 3
After a week of recovery, the effects of treatment were evaluated visually by comparison to untreated controls. The results are listed in Table 4. In this Table 4, plant damage was graded on a scale of 0 to 5. 0 represents 0-10% damage, 1 represents 11-30%
2 represents 31-60% damage; 3 represents damage of 31-60%;
represents 61-5 Oes damage, 4 represents 81-99% damage, and 5 represents 100% kill.

A dash (-) means no experiment was performed.

The names of the test plants are as follows: Wheat Or Oat Rg
Rye grass (Rh@grass) Jm Hix
(Japanese m1ll@t) B Barley (Barley) P Ento (P・I→ Ip Mexican Scamonia (Ipom@a) Ms
Mustard Sf Sunflower Table 4 4 kg/ha Wh JmRg Ot B P Ip
Ms Sf Table 4 (continued) A ′kg/ha WhJmRgOtBPIpMs
Sf7 1.0 45554000-8 1.
0 5555550130.25 5 5
5 5 5 - -- -0.0625 5 5
5 5 5 - - - -9 1.0 555
5533420.25 5 5 5 5 5-
− − −0.0625 5 5 5 5 5 −
- - -10 1.0 5555500-00
．． 25 5 5 5 5 5 - - - -
11 1.0 5555500-20.25
55555-1-- Example 12 The compound was formulated for testing by mixing the appropriate amount with an emulsion of 55555-1. The emulsion contained 1 span of 21.99/l in methylcyclohexanone.
80 and 78.211/l 6 tween (Tus・n
)' Soomj 160 g of a solution containing 20 with water.
It was prepared by diluting . “Snow chin (Spa)
n) '80 Fi, a trademark for a surfactant consisting of sorbitan monolaurate. “TWe＊n
) '20 is a trademark for a surfactant consisting of a condensate of sorbitan monolaurate and 20 molar proportions of ethylene oxide. 5 d of emulsion containing the test compound was then diluted to 40 d with water and sprayed on young potted plants named in Table 5 below (post-emergence application).

Damage to the test plants was evaluated after 14 days on a scale of θ~5.

where O is 0-20% damage and 5 is complete kill. The extent of herbicidal damage was assessed by comparison with untreated control plants. The results are listed in Table 5 below. A dash (-) means that the experiment was not performed.

The names of the test plants were as follows: Nb) Maizs WW Autumn wheat Re Rice (Rlc・) Br Wheat myosuroides ) St Green foxtail (5 etar fish avl
rid1m) halep・n■) Ag Agropyron r@
pent) below P white table 5

Claims (1)

[Claims] 1. A compound represented by the following formula I. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I In the formula, Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
4-alkylsulfamoyl, di(C_1-C_4alkyl)sulfamoyl, carboxy and trifluoroacetylamino; R^1 is selected from the group consisting of hydrogen, an acyl group, and an inorganic or organic cation; R^2 is C_1-C_6 alkyl, C_2-C_6 alkenyl, C_2-C_6 haloalkenyl, C_3-C6
alkynyl, and substituted C_1-C_6 alkyl, wherein said alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl, and substituted phenyl, and the benzene ring of said substituted phenyl is substituted with halogen and C_1-C
R^3 substituted with 1 to 3 substituents selected from the group consisting of
selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
-C_6alkoxy)carbonyl. 2. In the formula, Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
4-alkylsulfamoyl, di(C_1-C_4alkyl)sulfamoyl, carboxy and trifluoroacetylamino, R^1 is hydrogen, C_2-C_6 alkanoyl, benzoyl and substituted benzoyl (the benzene ring of said substituted benzoyl) is substituted with 1 to 3 substituents selected from the group consisting of halogen, nitro, C_1-C_6 alkyl and C_1-C_6 alkoxy) and an inorganic or organic cation; Organic cations include alkali metals, alkaline earth metals,
selected from transition metals, ammonium ions, and tri- and tetra(alkyl)ammonium ions, where alkyl is selected from C_1-C_6 alkyl and C_1-C_6 hydroxyalkyl, and R^2 is C_1-C_6 alkyl, C_2 -C_6 alkenyl, C_2-C_6 haloalkenyl, C_3-C_
6 alkynyl, and substituted C_1-C_6 alkyl, wherein said alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl, and substituted phenyl, and the benzene ring of said substituted phenyl is substituted with halogen and C_1-
substituted with 1 to 3 substituents selected from the group consisting of C_6 alkyl), R^
3 is selected from the group consisting of C_1-C_6 alkyl;
and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
2. A compound according to claim 1 selected from the group consisting of -C_6alkoxy)carbonyl. 3. In the formula, Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
R^1 is selected from the group consisting of hydrogen, C_2-C_6 alkanoyl and alkali metal cations, R^2 is C_1-C_6 alkyl, C_1-C_6 haloalkyl, C_2-C_6 alkenyl, C_2-C_6
selected from the group consisting of haloalkenyl and C_3-C_6 alkynyl, R^3 is selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
3. A compound according to claim 1 or 2 selected from the group consisting of -C_6 alkoxy)carbonyl. 4, In the formula, Y is C_1-C_6 alkylsulfonyl, C_1-C_
6-haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is selected from the group consisting of amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino selected, Z is hydrogen, halogen, C_1-C_4 alkyl and C
selected from the group consisting of _2-C_4 alkanoyl, R
^1 is selected from the group consisting of hydrogen, C_2-C_6 alkanoyl and alkali metal cations, R^2 is selected from the group consisting of C_1-C_6 alkyl, C_2-C_6 alkenyl and C_3-C_6 alkynyl, and R^3 is 4. A compound according to any one of claims 1 to 3, selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen. 5. In the formula, Y is C_1-C_4 alkylsulfonyl, C_1-C_
4 haloalkylsulfonyl, C_2-C_4 haloalkanoyl, carbamoyl, thiocarbamoyl, C_1-C
_4 alkylcarbamoyl and C_1-C_4 alkylthiocarbamoyl, Z is selected from the group consisting of hydrogen, halogen, methyl and C_1-C_4 alkanoyl, R^1 is selected from hydrogen and an alkali metal cation, ^2 is selected from the group consisting of C_1-C_4 alkyl, C_2-C_4 alkenyl and C_3-C_4 alkynyl; R^3 is selected from C_1-C_4 alkyl; and R^4 is hydrogen. The compound according to any one of Items 1 to 4. 6, where Y is selected from the group consisting of trifluoromethanesulfonyl, trifluoroacetyl, trichloroacetyl, carbamoyl, ethylthiocarbamoyl, methylcarbamoyl and propylcarbamoyl, Z is hydrogen or acetyl, and R^1 is hydrogen and R^2 is selected from ethyl, allyl and propargyl, R^3 is methyl, ethyl or propyl, and R^4 is hydrogen. Compound according to item 1. 7,2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3-trifluoroacetylaminophenyl)cyclohex-2-en-1-one, 2-[ 1-(ethoxyimino)propyl]-3-hydroxy-5-(3-acetyl-2,4,6-trimethyl-
5-trifluoroacetylaminophenyl)cyclohex-2-en-1-one, 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[3-(N'-methylureido)-2,4 , 6-trimethylphenyl]cyclohex-2-en-1-one, and 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[3-(N'-n-propylureido)-2
, 4,6-trimethylphenyl]cyclohex-2-en-1-one. 8. A herbicidal composition comprising a compound represented by the following formula I as an active ingredient and a carrier thereof. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I In the formula, Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
4-alkylsulfamoyl, di(C_1-C_4alkyl)sulfamoyl, carboxy and trifluoroacetylamino; R^1 is selected from the group consisting of hydrogen, an acyl group, and an inorganic or organic cation; R^2 is C_1-C_6 alkyl, C_2-C_6 alkenyl, C_2-C_6 haloalkenyl, C_3-C_
6 alkynyl, and substituted C_1-C_6 alkyl, wherein said alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl, and substituted phenyl, and the benzene ring of said substituted phenyl is substituted with halogen and C_1-
substituted with 1 to 3 substituents selected from the group consisting of C_6 alkyl), R^
3 is selected from the group consisting of C_1-C_6 alkyl;
and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
-C_6alkoxy)carbonyl. 9, where Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
4-alkylsulfamoyl, di(C_1-C_4alkyl)sulfamoyl, carboxy and trifluoroacetylamino, R^1 is hydrogen, C_2-C_6 alkanoyl, benzoyl and substituted benzoyl (the benzene ring of said substituted benzoyl) is substituted with 1 to 3 substituents selected from the group consisting of halogen, nitro, C_1-C_6 alkyl and C_1-C_6 alkoxy) and an inorganic or organic cation; Organic cations include alkali metals, alkaline earth metals,
selected from transition metals, ammonium ions, and tri- and tetra(alkyl)ammonium ions, where alkyl is selected from C_1-C_6 alkyl and C_1-C_6 hydroxyalkyl, and R^2 is C_1-C_6 alkyl, C_2 -C_6 alkenyl, C_2-C_6 haloalkenyl, C_3-C_
6 alkynyl, and substituted C_1-C_6 alkyl, wherein said alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl, and substituted phenyl, and the benzene ring of said substituted phenyl is substituted with halogen and C_1-
substituted with 1 to 3 substituents selected from the group consisting of C_6 alkyl), R^
3 is selected from the group consisting of C_1-C_6 alkyl;
and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
9. The composition of claim 8, wherein the composition is selected from the group consisting of -C_6 alkoxy)carbonyl. 10, where Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
R^1 is selected from the group consisting of hydrogen, C_2-C_6 alkanoyl and alkali metal cations, R^2 is C_1-C_6 alkyl, C_1-C_6 haloalkyl, C_2-C_6 alkenyl, C_2-C_6
selected from the group consisting of haloalkenyl and C_3-C_6 alkynyl, R^3 is selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
10. The composition of claim 8 or 9, wherein the composition is selected from the group consisting of -C_6 alkoxy)carbonyl. 11, where Y is C_1-C_6 alkylsulfonyl, C_1-C_
6-haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is selected from the group consisting of amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino selected, Z is hydrogen, halogen, C_1-C_4 alkyl and C
selected from the group consisting of _2-C_4 alkanoyl, R
^1 is selected from the group consisting of hydrogen, C_2-C_6 alkanoyl and alkali metal cations, R^2 is selected from the group consisting of C_1-C_6 alkyl, C_2-C_6 alkenyl and C_3-C_6 alkynyl, and R^3 is 11. A composition according to any one of claims 8 to 10, selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen. 12, where Y is C_1-C_4 alkylsulfonyl, C_1-C_
4 haloalkylsulfonyl, C_2-C_4 haloalkanoyl, carbamoyl, thiocarbamoyl, C_1-C
_4 alkylcarbamoyl and C_1-C_4 alkylthiocarbamoyl, Z is selected from the group consisting of hydrogen, halogen, methyl and C_1-C_4 alkanoyl, R^1 is selected from hydrogen and an alkali metal cation, ^2 is selected from the group consisting of C_1-C_4 alkyl, C_2-C_4 alkenyl and C_3-C_4 alkynyl; R^3 is selected from C_1-C_4 alkyl; and R^4 is hydrogen. The composition according to any one of Items 8 to 11. 13, where Y is selected from the group consisting of trifluoromethanesulfonyl, trifluoroacetyl, trichloroacetyl, carbamoyl, ethylthiocarbamoyl, methylcarbamoyl and propylcarbamoyl, Z is hydrogen or acetyl, and R^1 is hydrogen. and R^2 is selected from ethyl, allyl and propargyl, R^3 is methyl, ethyl or propyl, and R^4 is hydrogen. Composition according to item 1. 14. The compound is 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3-trifluoroacetylaminophenyl)cyclohex-2-en-1-one , 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(3-acetyl-2.4,6-trimethyl-5-trifluoroacetylaminophenyl)cyclohex-2-en-1-one, 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[3-(N'-methylureido)-2.
4,6-trimethylphenyl]cyclohex-2-en-1-one, and 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[3-(N'-n-propylureido)-2
．． 4,6-trimethylphenyl]cyclohex-2-en-1-one, the composition according to any one of claims 8 to 13, selected from the group consisting of: 15. Applying an effective amount of a compound represented by formula I or a composition comprising an effective amount of a compound represented by formula I as an active ingredient and a carrier thereof to an undesirable plant or the growth environment of said plant. methods of severely damaging or killing undesirable plants, including: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I In the formula, Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
4-alkylsulfamoyl, di(C_1-C_4alkyl)sulfamoyl, carboxy and trifluoroacetylamino; R^1 is selected from the group consisting of hydrogen, an acyl group, and an inorganic or organic cation; R^2 is C_1-C_6 alkyl, C_2-C_6 alkenyl, C_2-C_6 haloalkenyl, C_3-C_
6 alkynyl, and substituted C_1-C_6 alkyl, wherein said alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl, and substituted phenyl, and the benzene ring of said substituted phenyl is substituted with halogen and C_1-
substituted with 1 to 3 substituents selected from the group consisting of C_6 alkyl), R^3 is selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen , C_1-C_6 alkyl and (C_1
-C_6alkoxy)carbonyl. 16, where Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
4-alkylsulfamoyl, di(C_1-C_4alkyl)sulfamoyl, carboxy and trifluoroacetylamino, R^1 is hydrogen, C_2-C_6 alkanoyl, benzoyl and substituted benzoyl (the benzene ring of said substituted benzoyl) is substituted with 1 to 3 substituents selected from the group consisting of halogen, nitro, C_1-C_6 alkyl and C_1-C_6 alkoxy) and an inorganic or organic cation; Organic cations include alkali metals, alkaline earth metals,
selected from transition metals, ammonium ions, and tri- and tetra(alkyl)ammonium ions, where alkyl is selected from C_1-C_6 alkyl and C_1-C_6 hydroxyalkyl, and R^2 is C_1-C_6 alkyl, C_2 -C_6 alkenyl, C_2-C_6 haloalkenyl, C_3-C_
6 alkynyl, and substituted C_1-C_6 alkyl, wherein said alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl, and substituted phenyl, and the benzene ring of said substituted phenyl is substituted with halogen and C_1-
substituted with 1 to 3 substituents selected from the group consisting of C_6 alkyl), R^
3 is selected from the group consisting of C_1-C_6 alkyl;
and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
16. The method of claim 15, wherein the method is selected from the group consisting of -C_6 alkoxy)carbonyl. 17, where Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
R^1 is selected from the group consisting of hydrogen, C_2-C_6 alkanoyl and alkali metal cations, R^2 is C_1-C_6 alkyl, C_1-C_6 haloalkyl, C_2-C_6 alkenyl, C_2-C_6
selected from the group consisting of haloalkenyl and C_3-C_6 alkynyl, R^3 is selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
17. The method of claim 15 or 16, wherein the method is selected from the group consisting of -C_6 alkoxy)carbonyl. 18, where Y is C_1-C_6 alkylsulfonyl, C_1-C_
6-haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is selected from the group consisting of amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino selected, Z is hydrogen, halogen, C_1-C_4 alkyl and C
selected from the group consisting of _2-C_4 alkanoyl, R
^1 is selected from the group consisting of hydrogen, C_2-C_6 alkanoyl and alkali metal cations, R^2 is selected from the group consisting of C_1-C_6 alkyl, C_2-C_6 alkenyl and C_3-C_6 alkynyl, and R^3 is Claims 15-17 selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen.
The method described in any one of paragraphs. 19, where Y is C_1-C_4 alkylsulfonyl, C_1-C_
4 haloalkylsulfonyl, C_2-C_4 haloalkanoyl, carbamoyl, thiocarbamoyl, C_1-C
_4 alkylcarbamoyl and C_1-C_4 alkylthiocarbamoyl, Z is selected from the group consisting of hydrogen, halogen, methyl and C_1-C_4 alkanoyl, R^1 is selected from hydrogen and an alkali metal cation, ^2 is selected from the group consisting of C_1-C_4 alkyl, C_2-C_4 alkenyl and C_3-C_4 alkynyl; R^3 is selected from C_1-C_4 alkyl; and R^4 is hydrogen. 15
The method according to any one of Items 1 to 18. 20, where Y is selected from the group consisting of trifluoromethanesulfonyl, trifluoroacetyl, trichloroacetyl, carbamoyl, ethylthiocarbamoyl, methylcarbamoyl and propylcarbamoyl, Z is hydrogen or acetyl, and R^1 is hydrogen and R^2 is selected from ethyl, allyl and propargyl, R^3 is methyl, ethyl or propyl, and R^4 is hydrogen.
The method described in any one of paragraphs. 21, the compound is 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3-trifluoroacetylaminophenyl)cyclohex-2-en-1-one , 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(3-acetyl-2.4,6-trimethyl-5-trifluoroacetylaminophenyl)cyclohex-2-en-1-one, 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[3-(N'-methylureido)-2.
4,6-trimethylphenyl]cyclohex-2-en-1-one, and 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[3-(N'-n-propylureido)-2
．． 4,6-trimethylphenyl]cyclohex-2-en-1-one,
21. The method according to any one of clauses 20. 22. A method according to any one of claims 15 to 21, wherein the compound is applied at a rate ranging from 0.005 to 20 kg/ha. 23. A compound represented by the following formula I or a composition comprising a compound represented by the following formula I and its carrier as an active ingredient is added to a dicotyledonous crop or the growth environment of said crop to severely damage monocotyledonous weeds or selectively inhibiting the growth of monocot weeds in a dicotyledonous crop, comprising applying an amount sufficient to kill but insufficient to substantially damage said crop. Method. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I In the formula, Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
4-alkylsulfamoyl, di(C_1-C_4alkyl)sulfamoyl, carboxy and trifluoroacetylamino; R^1 is selected from the group consisting of hydrogen, an acyl group, and an inorganic or organic cation; R^2 is C_1-C_6 alkyl, C_2-C_6 alkenyl, C_2-C_6 haloalkenyl, C_3-C_
6 alkynyl, and substituted C_1-C_6 alkyl, wherein said alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl, and substituted phenyl, and the benzene ring of said substituted phenyl is substituted with halogen and C_1-
substituted with 1 to 3 substituents selected from the group consisting of C_6 alkyl), R^
3 is selected from the group consisting of C_1-C_6 alkyl;
and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
-C_6alkoxy)carbonyl. 24, where Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
4-alkylsulfamoyl, di(C_1-C_4alkyl)sulfamoyl, carboxy and trifluoroacetylamino, R^1 is hydrogen, C_2-C_6 alkanoyl, benzoyl and substituted benzoyl (the benzene ring of said substituted benzoyl) is substituted with 1 to 3 substituents selected from the group consisting of halogen, nitro, C_1-C_6 alkyl and C_1-C_6 alkoxy) and an inorganic or organic cation; Organic cations include alkali metals, alkaline earth metals,
selected from transition metals, ammonium ions, and tri- and tetra(alkyl)ammonium ions, where alkyl is selected from C_1-C_6 alkyl and C_1-C_6 hydroxyalkyl, and R^2 is C_1-C_6 alkyl, C_2 -C_6 alkenyl, C_2-C_6 haloalkenyl, C_3-C_
6 alkynyl, and substituted C_1-C_6 alkyl, wherein said alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl, and substituted phenyl, and the benzene ring of said substituted phenyl is substituted with halogen and C_1-
substituted with 1 to 3 substituents selected from the group consisting of C_6 alkyl), R^
3 is selected from the group consisting of C_1-C_6 alkyl;
and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
24. The method of claim 23, wherein the method is selected from the group consisting of -C_6 alkoxy)carbonyl. 25, where Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
R^1 is selected from the group consisting of hydrogen, C_2-C_6 alkanoyl and alkali metal cations, R^2 is C_1-C_6 alkyl, C_1-C_6 haloalkyl, C_2-C_6 alkenyl, C_2-C_6
selected from the group consisting of haloalkenyl and C_3-C_6 alkynyl, R^3 is selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
25. The method of claim 23 or 24, wherein the method is selected from the group consisting of -C_6 alkoxy)carbonyl. 26, where Y is C_1-C_6 alkylsulfonyl, C_1-C_
6-haloalkylsulfonyl, C_2-C_6 haloalkanoyl selected from the group consisting of R^5CO and R^5CS, where R^5 is selected from the group consisting of amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino and Z is hydrogen, halogen, C_1-C_4 alkyl and C
selected from the group consisting of _2-C_4 alkanoyl, R
^1 is selected from the group consisting of hydrogen, C_2-C_6 alkanoyl and alkali metal cations, R^2 is selected from the group consisting of C_1-C_6 alkyl, C_2-C_6 alkenyl and C_3-C_6 alkynyl, and R^3 is Claims 23-25 selected from the group consisting of C_1-C_6 alkyl, and R^4 is hydrogen.
The method described in any one of paragraphs. 27, where Y is C_1-C_4 alkylsulfonyl, C_1-C_
4 haloalkylsulfonyl, C_2-C_4 haloalkanoyl, carbamoyl, thiocarbamoyl, C_1-C
_4 alkylcarbamoyl and C_1-C_4 alkylthiocarbamoyl, Z is selected from the group consisting of hydrogen, halogen, methyl and C_1-C_4 alkanoyl, R^1 is selected from hydrogen and an alkali metal cation, R ^2 is selected from the group consisting of C_1-C_4 alkyl, C_2-C_4 alkenyl and C_3-C_4 alkynyl; R^3 is selected from C_1-C_4 alkyl; and R^4 is hydrogen. 23
27. The method according to any one of Items 26 to 26. 28, where Y is selected from the group consisting of trifluoromethanesulfonyl, trifluoroacetyl, trichloroacetyl, carbamoyl, ethylthiocarbamoyl, methylcarbamoyl and propylcarbamoyl, Z is hydrogen or acetyl, and R^1 is hydrogen and R^2 is selected from ethyl, allyl and propargyl, R^3 is methyl, ethyl or propyl, and R^4 is hydrogen.
The method described in any one of paragraphs. 29, the compound is 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3-trifluoroacetylaminophenyl)cyclohex-2-en-1-one , 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(3-acetyl-2.4,6-trimethyl-5-trifluoroacetylaminophenyl)cyclohex-2-en-1-one, 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[3-(N'-methylureido)-2.
4,6-trimethylphenyl]cyclohex-2-en-1-one, and 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[3-(N'-n-propylureido)-2
．． 4,6-trimethylphenyl]cyclohex-2-en-1-one, selected from the group consisting of:
The method according to any one of paragraph 28. 30. A method according to any one of claims 23 to 29, wherein said compound is applied at a rate ranging from 0.005 to 20 kg/ha. 31. Compound represented by the following formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I (In the formula, Y is C_1-C_6 alkylsulfonyl, C_1-C_
6 haloalkylsulfonyl, C_2-C_6 haloalkanoyl, R^5CO and R^5CS, where R^5 is hydroxy, C_1-C_6 alkoxy, amino, C_1-C_6 alkylamino and di(C_1-C_6 alkyl)amino, Z is hydrogen, halogen, C_1-C_4 alkyl, C_2
-C_4 alkanoyl, sulfamoyl, C_1-C_
4-alkylsulfamoyl, di(C_1-C_4alkyl)sulfamoyl, carboxy and trifluoroacetylamino; R^1 is selected from the group consisting of hydrogen, an acyl group, and an inorganic or organic cation; R^2 is C_1-C_6 alkyl, C_2-C_6 alkenyl, C_2-C_6 haloalkenyl, C_3-C_
6 alkynyl, and substituted C_1-C_6 alkyl, wherein said alkyl group is substituted with a substituent selected from the group consisting of halogen, phenyl, and substituted phenyl, and the benzene ring of said substituted phenyl is substituted with halogen and C_1-
substituted with 1 to 3 substituents selected from the group consisting of C_6 alkyl), R^
3 is selected from the group consisting of C_1-C_6 alkyl;
and R^4 is hydrogen, C_1-C_6 alkyl and (C_1
-C_6alkoxy)carbonyl) having the following formula Xc: ▲ Numerical formulas, chemical formulas, tables, etc. By reacting with an alkoxyamine derivative of the following formula XVIII: H_2NOR^2 , 3-dione derivative with hydroxylamine, and the oxime intermediate of the following formula XIX: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ) to produce the compound of formula II, and optionally the compound of formula II is converted into a compound of the formula XX I :R^1L
A method of synthesizing a compound of formula I, comprising reacting with a compound of formula I, wherein L is a leaving group, to produce a compound of formula I.