JPS6165846A - Alpha,beta-unsaturated carboxylic acid, herbicide and plant growth regulator comprising it as active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I {at least one of X<1>-X<4> is group shown by the formula II [Ar is (halogen-, cyano-substituted) aromatic hydrocarbon group; R<7> and R<8> are H, halogen, cyano, etc.; n is 1-10], the others are H, or lower alkyl; R<1>-R<5> are H, halogen, lower alkyl, lower alkenyl, etc.; R<6> is -OR<12> (R<12> is H or 1-15C hydrocarbon group which may contain 0, etc., -SR<12>, etc.; k is 0-15; l is 0 or 1; m is 0-10}. EXAMPLE:Ethyl 8-(2,4-dichlorophenoxyacetyloxy)-5,9-dimethyl-deca-2,4,9-trienoate. USE:A herbicide and a plant growth regulator. PREPARATION:A compound shown by the formula III is reacted with a compound shown by the formula IV to give a compound, which is epoxidized with a peroxide, and thermally decomposed to give a compound shown by the formula V. This compound is reacted with a compound shown by the formula VI to give a compound shown by the formula I where X<1> is group shown by the formula II, R<1> and R<2> are H, and lower alkyl, and k is 3.

Description

Detailed Description of the Invention (al) Technical Field The present invention relates to novel unsaturated aliphatic carbonic acids, and novel herbicides and plant growth regulators containing the same as active ingredients. relates to a herbicide and a plant growth regulator containing specific α,β-unsaturated carboxylic acids and at least one type thereof as active ingredients.

(bl Prior Art) It is known that a number of aliphatic carboxylic acids exhibit various physiological activities, such as sorbic acid, which is a bactericidal agent used to prevent spoilage of foods such as cheese (U.S. Pat. 3139378) and that 3-decyne Enoki has cholesterol synthesis inhibitory activity (Biochemical Journal (Biochem, J)).

147, pp. 531-539 (1975). On the other hand, Japanese Patent Publication No. 47-41005 or Agricultural Biological Chemistry (Agri, Biol, Chem) + 45 volumes,
2769-2773 (1981), β-(N-phenyl-N-methyl)amino-α-cyanoacrylic acid ester exhibits herbicidal activity, and the Hill reaction (photochemical oxygen generation by free phyllodes) Reaction) It is disclosed that it has inhibitory activity.

The present inventors focused on the physiological activity of such carboxylic acids, and with the aim of obtaining a herbicide having the desired activity, we added each derivative thereof to physiological and *J Physical Chemistry. As a result of extensive research, we have found that unsaturated carboxylic acids with a specific structure of α and β double bonds have excellent herbicidal effects on various plants, and that It has excellent herbicidal effects in both escape and post-emergence treatments, and in foliage treatment, it has a 91% effectiveness against broad-leaved weeds.
1 shows an excellent effect. Furthermore, when used at a relatively low concentration, it has the effect of breaking the dormancy of plant buds, such as promoting the germination of new shoots in Dais, or regulating plant growth by overcoming the so-called senescence phenomenon in which one leaf vein turns red. The present invention was achieved based on the discovery that the present invention has an effect.

tdl Constitution of the Invention The present invention is based on the general formula % (at least 1 i [W is the formula Ar-o+c+nco (where Ar is a hagen atom, a cyano group, or a nitoxy group).

Lower alkyl group 3 formula -OR' (R' is a hydrogen atom.

An acyl group having a carbon number of 2 to 10, or a cR cumulative atom.

Group 9 Formula -8R represented by a sulfur atom and a nitrogen atom (both of which are halogen-substituted or unsubstituted hydrocarbon groups having 1 to 10 carbon atoms and which may contain one atom)
'(R' is defined as above) and is a hydrogen atom or a hydrocarbon group having 1 to 1° of carbon atoms, and RIG and R11 jointly form a ring. may be formed. ) is a substituted or unsubstituted aromatic hydrocarbon group with one or more selected from the groups represented by;
-W'L R' are the same or different, hydrogen group, /
~a-gen atom.

Cyano group, nido a group, lower alkyl group, the above formula -OR'
or a group represented by the above formula -8R9; n means a convergence of 1 to 1o. ], the other Xl and XI are hydrogen atoms or lower alkyl groups; R' to RS are the same or different,
R6 is a hydrogen atom, a halogen atom, a cyano group, a nido group, a substituted or unsubstituted lower alkyl group, or a lower alkyl group; R6 is of the formula -OR'! (However, R" may contain at least one atom selected from a hydrogen atom, an oxygen atom, an atom, and a #A atom, and the number of carbon atoms is 1.
~15 hydrocarbon groups. ) 1 set-8R” (However, R
12 is defined in the same manner as above) and O in the above.
is an integer of ~15, l is O or 1, m is 0~l
O means an integer. ) and their functional salts α-β-unsaturated carboxylic acids, the α,β
- A urine herb containing as an active ingredient at least one carboxyl selected from unsaturated carboxylic acids, and a plant growth regulator containing at least one selected from α- and β-unsaturated carboxylic acids as an active ingredient. It is something.

The present invention will be explained in more detail below.

The α,β-unsaturated carboxylic acid orchid Vc according to the present invention is
It includes those represented by the above general formula (I). That is, the compound represented by the general formula CI) has two X bonds at the α and β positions, and a specific R'' bond, and the terminal portion having a carboxyl group has a carboxyl group, a carboxyalkyl group, and a substituted carboxyl group. It is characterized by being composed of esters such as hokidialkyl, or acid amides.

XI and XI in the above formula (1) are the same or different, and each is a water atom, a lower alkyl group, or R' L) l 11 , and at least one of XI and XI is the same as or different from the above formula %
Formula % Here, the lower alkyl group is preferably a linear or branched alkyl group having 1 to 5 carbon atoms, such as a methyl group, ethyl group, or n-propyl group.

Iso-propyl group, n-butyl group, 5ee-butyl group, tart-methyl group and the like are mentioned as examples of A ψ, and methyl group and dithyl group are preferably used.

aromatic hydrocarbon group or lower alkyl group.

hagen atom, cyano group, nido σ group, f:, -OR'
.

(It also means the same group as defined in IJ.) It is an aromatic hydrocarbon group substituted with at least one group selected from the groups shown in (IJ). The aromatic hydrocarbon group is preferably a phenyl group or a naphthyl group.

As such halogen atoms, halogen atoms, chlorine, bromine, etc. are used, and t+ and especially VC chlorine are preferably used.

Also, a9 in the formulas -0R9 and -SR' is a hydrogen atom.

An acyl group having 2 to IO carbon atoms or an oxygen atom.

It is a hydrocarbon group having 1 to 10 carbon atoms which may contain a small number of atoms selected from iodine atoms and nitrogen atoms.

Here, the acyl group having 2 to 10 carbon atoms refers to a linear or branched saturated or unsaturated aliphatic acyl group, a saturated aromatic ring-substituted aliphatic acyl group (. is an unsaturated aliphatic acyl group, These include aromatic acyl groups, such as fluorine and chlorine.

It may be substituted with a single or multiple zs 6 atoms such as bromine (. Typical examples of the acyl group are an acetyl group and a propionyl group.

Butyryl group, imbutyryl group, valeryl group.

invaleryl group, pivaloyl group, acryloyl group, methacryyl group, tarotonoyl group.

Go phase or unsaturated aliphatic acyl group such as ink atonoyl group, b-abio ayl group; phenylacetyl group, 1
-Phenylb a pionyl 1l 15.3-phenylpropionyl Ji, I-phenylzutyryl group, 3-phenylmethyl group.

4-phenylbutyryl group. 1-phenyl ymphyl group, 3-phenyl isopylyl group.

p-tolylacetyl group, 0-)lylacetyl i, m-to-11lylacetyl group, nonnasoyl group.

3-Phenylmethac IJ A saturated or provisionally unsaturated aliphatic acyl group substituted with an aromatic ring such as ayl group; benzoyl group, 〇-toluoyl group, m-toluoyl group, p
-) Aromatic acyl groups such as luoyl groups, etc.

A small number of atoms selected from oxygen atoms, oxygen atoms and nitrogen atoms (
A hydrocarbon group having 1 to 10 carbon atoms refers to a saturated or unsaturated aliphatic hydrocarbon group, a saturated or unsaturated alicyclic hydrocarbon group, or an aromatic ring. Substituted saturation or unsaturated! Hydrocarbon groups in the @ phase.

aromatic hydrocarbon groups, etc., and these include fluorine, chlorine,
Single or multiple substitutions may be made with 7SOgen atoms such as bromine. Typical examples of the hydrocarbon group having 1 to 10 carbon atoms include a methyl group, an ethyl group, and a globyl group.

pochyl group, pentyl group, hequinyl group, heptyl group, octyl group, 2-ethyl-hexyl group.

Alkyl groups such as nonyl group and decyl group; ethynyl group, various butenyl groups, and butenyl groups.

Pentenyl group, hexenyl group, hexenyl group.

ocnanyl group, nonenyl group, decenyl group, and realkenyl group; or those whose hydrogen atoms are substituted with an alicyclic hydrocarbon group, such as cyclohexylmethyl group, cyclohexylethyl group, cyclohexenylethyl4 nato; Nk a Saturated alicyclic hydrocarbon groups such as pyl group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group in each column, and six types of dimethylcyclohexyl groups; Nk a
Pebutenyl group.

Unsaturated alicyclic hydrocarbon groups such as Schiff a hexenyl group, methylnochlorohexenyl group of each +I[, dimethylcyclohexenyl/l/ group; phenylmethyl group, phenylethyl group, phenylbu avir group of each a[, phenylbutyl group,
Tolylmethyl group, tolylethyl group, tolylpropyl group, ethylphenylmethyl group, dimethylfuninylmethyl group, nannamyl group, various phenyl 7'-benyl groups,
Phenylbutenyl 4. Saturated or unsaturated aliphatic hydrocarbon groups containing d% of aromatic rings such as tolylmethyl group, tylphenylethynyl group, dimethylphenylethynyl group; phenyl group, tolyl group, xylyl group, ethylphenyl group, naphthyl group, etc. aromatic hydrocarbon groups, etc. Further, as examples of these hydrocarbon groups having 1 to 10 carbon atoms containing at least one atom selected from rIl atoms, inert atoms, and nitrogen atoms, there are, for example, methoxy/methyl groups.

Ethoxymethyl group, aboxymethyl group, butoxymethyl group, methoxyethyl group, ethosethyl group, polyquinoethyl group, cycloethyl group, methoxyethyl group, ethoxyethyl group, ethoxyethyl group, tetrahydroxyethyl group
Villanyloquinethyl group, methylthiomethyl group, dicarboxylthiomethyl group, p-avirthiomethyl group.

Methyl J-nonycyl group, ethylthioethyl group.

Methylthioethoxyethyl group, ethylthioethoxyethyl group, 2-methyl7minoethyl group.

2-ethylamine ethyl group, 2-propylaminoethyl group, Fe/xymethyl group, phenoxyethyl group, various tolyloquinemethyl groups.

Tolyloyaethyl group, phenylthiomethyl group, phenylthioethyl group, various tolyl 1000methyl groups, tolyl 1000001 groups, anilinomethyl group, anilinoethyl group, various methylanilinomethyl groups, methylanilinomethyl group Examples include.

It also includes those in which these hydrocarbon groups having 1 to 1 I+ are substituted with halogen atoms such as fluorine, chlorine, and bromine, such as CIO methyl group, fluoro a methyl group, and ru group, ri(10butyl group, dichloroethyl group.

3-ri00 propenyl group, 3-ri aroatenyl group +
2. l! -dichlorophenylmethyl group.

2.4-k a0 phenylethyl group, 2-methyl-4-
riao phenylmethyl group, 14-cyclooo phenyl group,
A representative example thereof is 2-methyl-4-aryl phenyl group.

It is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, and RIG and R'' may cooperate with each other to form a ring. Examples of the closed hydrocarbon group include a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms. Aliphatic hydrocarbon group.

These include aromatic hydrocarbon groups, which may be substituted with .~a atoms, etc. The aliphatic hydrocarbon groups having 1 to 10 carbon atoms are linear or branched. For example, alkyl groups such as methyl group, ethyl group, various polypyl groups, butyl group, pentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group; ethynyl group.

Various butenyl groups, butenyl groups, pentenyl groups, hexenyl groups, heptenyl groups, octenyl groups, nonenyl groups,
Flukenyl radicals such as decenyl groups, or those in which the hydrogen atom thereof is substituted with an alicyclic hydrocarbon group or an aromatic hydrocarbon group, such as a hexenylmethyl group, a hexylethyl group, or a cyclohexenylethyl group.

Examples include phenylmethyl group, phenylethyl group, etc.

In addition, the aromatic hydrocarbon group having 1 to 10 carbon atoms is flj
For example, phenyl group, tolyl group, dimethylphenyl group,
There are naphthyl groups.

Furthermore, examples of Fl in which the hydrocarbon group at carbon a1 to a10 is substituted with a halogen atom include, for example, a chloromethyl group and a trifluoromethyl group.

Chlominityl (ff) propyl group, dichloroethyl group, 3-lya propenyl group, 3-lya lobutenyl!, 2,4-dichloro-a phenylmethyl group, various types of clo-a phenyl group, sil .

a phenyl group, etc.

Furthermore, when RIG and R'' cooperate with each other to form a ring, they may form a cluster through 111 or more atoms selected from nitrogen atoms, oxygen atoms, or sulfur atoms, but if two of these atoms In the above case, it is preferable to use another hydrocarbon residue such as an alkylene group, and the total number of the atoms is preferably 1 to 5, and they may be the same or different. The number of members forming the ring is 3
-8 is preferred, for example 7 piperidi groups, 1 piperazino group
Examples include morpholino group.

Such R", R" is usually a hydrogen atom, a saturated or unsaturated aliphatic hydrocarbon group, or an aromatic hydrocarbon group.
groups are preferably used, with halogen-substituted aromatic hydrocarbon groups being particularly preferred.

Also, R? , ua are the same or different, hydrogen atoms,
A lower alkyl group, a helgen atom, a cyano group, a nido a group, and a group represented by the formula -OR', -SR' OL
, Here, the lower alkyl group is preferably a linear chain having 1 to 5 carbon atoms or an alkyl group awaiting branching, and specific examples include a methyl convex, ethyl group, Tanimune's avir group, butyl group, penotyl group, etc. It can be given as Further, specific examples of the halogen atom are fluorine, chlorine, and halogen, and have the formula -OR'.

Typical examples of the group represented by -8R" include Metquin group,
Ethoxy group, various types of abo-thio group, butoki-7 group, pentyloxy group, methylthio group.

2+ru chisai group, various a-pylthio groups, gutylthio groups,
Examples include a lower alkoxy group such as a penthylthio group or a lower alkylthio group. Among such ft7 and R8, hydrogen atoms, lower alkyl groups, halogen atoms, etc. are particularly preferably used.

n means an integer from 1 to ]0, preferably from 1 to 8;
Especially Kl~5 is preferable.

R' 0 Particularly preferably used as the formula Ar-0 (-C--C-0-) are, for example, 2+4-7 milphenoxyacetyl group, 2,4.5-) II Enoxyacetyl group, 2-methyl-4-chlorophenoxyacetyl group, 2-methyl-4-chlorophenoquine isoproxy group, 2,4-dicumylphenoxy-butoxy group, 2.
4-dicalphenoquine-see-7')quine group, and the like. Further, the number of the above general formulas (1) &'c is preferably 2 or less.

Formula (I) K-Oru, R', R'', R', R
', R' +! Same or different, hydrogen atom, halogen atom.

sia/group, nido a group, substituted and unsubstituted lower alkyl groups; lower alkenyl group, and the above. Here as a halogen atom (fluorine.

Examples include salt, bromine, and iodine, but fluorine, chlorine, and bromine are particularly preferred. Examples of unsubstituted lower alkyl groups include methyl and ethyl.

Various propyl, butyl, pentyl alkyl groups having 1 to 5 carbon atoms, and lower alkyl groups having 1.2
-Dibodiethyl group.

1.2-evotinpyl scale, l,2-epoxib a-pyr group, 2,3-ethyl, +nee v-pyl group.

1.2-Epoxymethyl group. Epoxyalkyl groups such as 2,3-epoxy 7-nal group, 1,2-epoxybentyl group, 2,3-epoxybentyl group, and the above-mentioned lower alkyl groups substituted with halogens such as fluorine, chlorine, and bromine are added. . Further, as the lower alkenyl group, those having 1 to 5 carbon atoms are preferably used, such as an ethynyl group.

1-butenyl group, 2-bupenyl group, 1-butenyl group, 2-funanyl &, 3-cutynyl lA, I-pentenyl group, 2-pentenyl group.

, (-pentenyl group, 4-pentenyl group, I, 3-butanoenyl &, I+3-pencdienyl group.

2.4-pentadienyl group etc. Φ.

In the above formula (1),
1 is a hydrogen atom, or [9 elemental f, a hydrocarbon group having 1 to 15 carbon atoms which may have one atom] selected from sulfur atom and nitrogen atom. 6 Formula -8R1!
(However, R'' is the same group as above.

Here, the hydrocarbon group having 1 to 15 carbon atoms is an aliphatic hydrocarbon group having 1 to 15 carbon atoms.

Alicyclic hydrocarbon group having 3 to 15 carbon atoms and 6 to 15 carbon atoms
15 aromatic hydrocarbon groups are shown.

The aliphatic hydrocarbon group is linear or branched, saturated or unsaturated, and includes, for example, a methyl group, an ethyl group, various propyl groups, a butyl group, a hexyl group, and an off-thyl group. , tesyl group, dodecyl group, tetradecyl group, ethynyl group, propenyl group of each m, hecenyl group.

Examples include nonenyl group, dodecenyl group, etc., or those substituted with an alicyclic or aromatic hydrocarbon group, such as cyclohexylmethyl, cyclohexylmethyl, phenylmethyl, phenylethyl, etc.11. Among them, those having a carbon number of 1 to ]0 are preferred.

In addition, examples of the alicyclic hydrocarbon group having 3 to 15 carbon atoms include, for example, Nkuapensenrukyo, Shikuahekinru4, each 1
J

Dimethyl hexyl group, dimethyl hexyl group, cyclohexenyl! , each Ml has a dimethylchlorhexenyl group, and those having 3 to 10 carbon atoms are preferred.

Furthermore, examples of aromatic hydrocarbon groups having 6 to 5 carbon atoms include phenyl groups and various tolyl groups.

Examples include diethylphenyl group, naphthyl group, and mehandlunaphthyl group.

Further, the carbon 11Z hydrogen group having 1 to 15 carbon atoms is one or more oxygen atoms.

It may be separated by a nitrogen atom and/or a sulfur atom (for example, methquinethyl group, ethquinethyl group, etc.).

Ethoquinoethyl group, methyl/ethioethyl group, ethylthioethyl group, methylthioethyl group, ethylthioethoxyethyl group.

Phenoxymethyl group, phenoxymethyl group.

Naphthoxymethyl group, naphthoxyethyl group.

Phenoxyphenyl group, benzyloxyphenyl group. Examples include methylaminomethyl group, anilinomethyl group, and anilinoethyl group.

Further, the hydrocarbon group having 1 to 15 carbon atoms may be a substituted product of the above-mentioned ones, and examples of these halogen-substituted products include a methyl group, a a-methyl group, milomethyl group, di-ethyl group, 3-benyl group, 3-a-benyl group, 2,4-dichloromethyl group, 2,4-dichloromethyl group, 2 -Methyl-4-arialophenylethyl group and the like.

It is defined similarly.

On the other hand, k means an integer of θ to 15, preferably O to 10, particularly preferably θ to 7. l means an integer of O or 1. m represents O to 10, preferably O to 7, and particularly preferably θ to 5. In addition, here, l or m is 0
In the case of 0, it means a simple combination between the atoms on both sides in the formula CI). Also k.

When m is 2 or more, its R1, R2, ua and X4
are independent and may be the same or different.

Furthermore, for α,β-unsaturated phase unsaturated carbonic acids in opacity, A
Also included are functional salts of new compounds that retain the herbicidal effect of the compound represented by formula (1) above. Examples of the functional salts include alkali metal salts, alkaline earth metal salts, and salts with ammonium of the carboxylic acid.

Here, the alkali gold λA salts include lithium salts, sodium salts, potassium salts, etc., and the alkaline earth metal salts include carunum salts, magnonium salts, etc.

child or hydrocarbon having 1 to 20 carbon atoms; g group; R
14 is a hydrocarbon group having 1 to 20 carbon atoms. The charcoal; %
Hydrocarbon groups having 1 to 20 carbon atoms include aliphatic hydrocarbon groups having 1 to 20 carbon atoms, alicyclic hydrocarbon groups having 3 to 20 carbon atoms, and aromatic hydrocarbon groups having 6 to 20 carbon atoms. Indicates the group.

The aliphatic hydrocarbon group has a linear or branched structure, and is saturated or unsaturated, such as a methyl group, an ethyl group, various propyl groups, a ctyl group, a hexyl group, an octyl group, and a tesil group. , dodenyl group, tetrazofur group, octadecyl group, ethynyl group, p-benyl group of each ridge, hexenyl group, /nenyl group, tothycenyl group, etc., or those substituted with an alicyclic or aromatic hydrocarbon group, For example, cyclohexylmethyl, Schiff a hexylbu avir,
Examples include phenylmethyl, phenylethyl, etc. Among them, those having a charcoal number of 1 to 15 are preferred.

Examples of the aliphatic hydrocarbon group having 3 to 20 carbon atoms include a pentyl group, a hexyl group, and various methylcyclohexyl groups.

Examples thereof include a dimethyl hexyl group, a hexyl group, a hexenyl group, and various dimethyl hexenyl groups, among which those having 3 to 15 carbon atoms are preferred.

Furthermore, examples of aromatic hydrocarbon groups having 6 to 20 carbon atoms include phenyl groups and various tolyl groups.

Examples include diethylphenyl group, naphthyl group, and methylnaphthyl group.

Preferred hydrocarbon groups for R" and R" are saturated aliphatic or alicyclic hydrocarbon groups having 1 to 15 carbon atoms, and a hydrogen atom is also preferred as Has.

Preferred functional salts of the compound represented by the general formula CI) in terms of herbicidal activity in the present invention are alkali metal salts, ammonium salts, ethylamine salts, diethylamine salts, dimethylamine salts, bucviramine salts, dibupyramine salts, and Hexylamine salt, dicyclohexylamine salt, octylamine salt, decylamine salt. These include dodecylamine salt and detradenylamine salt.

Further, the unsaturated carboxylic group 11 of the present invention is a hydrochloride.

It may also be used in the form of organic or inorganic acid salts, such as sulfates, oxalates, sulfonates, and esters.

As a general method for producing the α,β-unsaturated carboxylic acids represented by the general formula (1) in the present invention, for example, as described below, the carhomol compound IW represented by the general formula (It)
α,β-unsaturated phase unsaturated bonic acid derivative (III) was synthesized by the ittig reaction, and further epoxycylated (IV) with peroxide.
iology Cal Chemistry)4
4 (11) 2709 (1980) to obtain compound (V), and the core compound and acid chloride (Vl)
By reacting, (■), one of the compounds of the present invention, can be produced.

S )C'' (II) Ga(lI[) (IV) R' 0 (V) (■) (However, in the above formula, X''''X',R'' ~, R',
Ar, l.

m and n are defined similarly to the above formula (I). ) The compound represented by the formula (I) in the present invention may be produced not only by this method but also by other commonly used methods.

Furthermore, any commonly used method may be used for producing the functional salts.

When using the herbicide of the present invention, the active ingredient, the α,β-unsaturated carboxyl group, may be treated as such, but it may also be treated in granules or in an aqueous phase agent.

1) It can also be used by processing it into any of the following formulations, such as tablets, emulsions, 9-grain tablets, flowable tablets, and suspensions. Herbicides in these formulations include talc, bentonite, and clay.

Solid carriers such as kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, ammonium sulfate, urea; Liquid carriers such as water, alcohol, ditau xane, acetone, 1,000 silane, cyclohexane, methylnaphthalene, dimethylformamide; alkyl sulfate esters, furkyl Sulfonic acid salts, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene diethylene alkylaryl ether, polyoxysulfate diethylene sorbitan monoalkylate.

Emulsifiers such as dinafthylmethane disulfonate.

Dispersant: Various adjuvants such as carpoxomethylcellulose, gum arabic, etc. or 24! Using the above, it is suitably blended with the unsaturated carboxylic acids, and manufactured by mixing, dissolution, granulation, etc. The herbicide of the present invention produced in this manner and in the form of a formulation usually has a
It is desirable to contain about 99% by weight, preferably about 0.1 to about 95% by weight, of the unsaturated carboxylic acids as an active ingredient.

It is preferably at least 10 parts, particularly preferably at least 50 parts, and preferably at most 9 parts.

When the herbicide in the form of a preparation containing the carboxylic acids themselves or the carboxylic acids ff of the present invention as an active ingredient is used, for example, in liquid or wet particulate form, it is usually used as a preparation agent. One or more surfactants may be present in a sufficient amount to readily disperse the active ingredient in water or oil. The term ``surfactant'' also includes, of course, wetting agents, 9 dispersing agents, HA clouding agents, layering agents and emulsifiers.

(When using the α,β-unsaturated carboxylic acids in EL as a herbicide containing it as an active ingredient,
Both the foliage treatment, which involves absorbing the acidic active ingredient from seeds and stems after germination, and the soil treatment, which involves absorbing the active ingredient from S and roots, exhibit a weak herbicidal effect.

Furthermore, the herbicide of the present invention exhibits an excellent herbicidal effect not only on annual weeds, but also on perennial weeds such as plantain and hemasuge. It also has the characteristic of being less harmful to rice plants, corn beetles, etc. Furthermore, when used at relatively low concentrations, it has the effect of breaking the dormancy of plant buds, and for example, the germination of new buds is promoted, and the so-called aging, which causes reddening of the kiln veins. /1 It also has plant growth-regulating effects that cause insects.

The present invention will be further explained below with reference to Examples, but the present invention is not limited to Examples V in any way.

Furthermore, in the examples, "parts" means "parts by weight."

Example 1 CH8C1(.

(1-1) H, C-C=CH-C)1. -CH,-
C=C1(-CH=C)I-COOEt[ethyl 5.9
3. Synthesis of 45.6 parts of 7-1,000-2,6-renyn-1-al and 60 parts of methylene salt in VC blur at room temperature. Triphenylcarboethoxymethylenephosphorane 125.3 iJ of methylene chloride (170 parts by volume) bath solution is added dropwise. Stir for about 4 hours after addition. After the reaction, methylene chloride was concentrated under reduced pressure, the precipitated crystals were separated, the P solution was further concentrated, and the residue was purified by distillation under reduced pressure to obtain 142 parts of the desired compound. Boiling point of compound 1 and 1, R, N
The MR spectrum data is as follows.

b-p 121~b +710.1630.1260,11401, Rv(α
-1); NMR (CCA!4), δ(P); 1.25 (3H), 1.60 (3) (), 1.67 (3
H).

1.90 (3H), 2.0-2.3 (4H).

4.13 (2H), 4.8-5.3(1)1).

5.60 (tH), 5.90 (xH), 7.40 (IH
) [Ethyl 8,9-epoxy-5,9-dimethyl-deca-2,4-genoate] Synthesis (1-1) Compound m + ro parts were mixed with salt (and cedar oak in 60 volumes i parts of methylene). , 15.5 parts of methylene chloride (40
0 parts by volume) Add the solution dropwise. After heating, stir at room temperature for 1 hour. After reaction, saturated hydrogen carbonate) + 1 um water solution, 1
The 0-line sodium bicarbonate IJum aqueous plate was further washed with 11@ of the 17 um water bath solution of hydrogen carbonate, and the +S layer was dried with 1.1 um of anhydrous sodium sulfate), and then condensed under reduced pressure. , Production #yJ Ken 1 Tsukagel Lamb Chromatograph (Wakogel C-2U O, MF1gK Benzene: Oa Ethyl =
5:1) to produce the given compound 6m 27. (I passed the first part.

1. of the compound. The R and NMR spectra are as follows.

1, Ry(α-') +710.163f), 12
7ONMR<CCl4), δ0; 1.25C6H, 1,27C3H.

1.5~LJ(2)i), 1.95(3Hn.

2.23(IH), 2.3-2.7(2)1).

4.15 (2Hn, 5.70 (1) 1), 5.9
6 (IH).

7.35(In) OH C ethyl 8-human cI + C 5,9-dimethyl-deca-
Synthesis (+-2) of 2,4,9-to1noe/ate] (+-2) to synthesize sita compound@22.0 parts, r:4:r synthetic aluminum (M@rk Co., Ltd. Art, l +777) 0. 24 parts were heated and stirred for 5 hours at 140-15° C. under a nitrogen atmosphere. The reaction mixture was filtered with I and washed with ethyl acetate. Predetermined compounds 1.
Got 5 copies. Compound 1. The R, NMR spectrum is as follows.

1, R ((v-') 35011.1720.163+1.1260.118
ONMR(CCA!4), δ(騨); 1.25(31(), 1.7U(3)(), t, 90(
3)i).

1.5-2.4 (4M), 2.9-3.3 (IH)
.

3.86 (I)I), 4.10 (2)i), 4
．． 80 (2M).

5.65 (+)i), 5.93 (IH), 7
,60 (1)1)OH,C)I.

32.38 parts of the compound synthesized in synthesis (1-3) of [ethyl 8-(2,4-dichlorophenoxy7cetylox7)-5,9-dimethyl-deca-2,4,9-trienoate], triethylamine While cooling a solution of 1.11 parts of benzene (24 parts by volume) on ice, 2,63 iftl of 2,4-dicalphenoxy acetyl chloride is added. After adding the mixture, stir at room temperature for about 4 hours. Add the reaction water and extract with ether. After drying the organic layer with anhydrous sulfuric acid, it was condensed under reduced pressure d1 and the product was transferred to a silica gel column chromatogram 7.
(Fuko-gel C-2'00.IN open solvent benzene: ethyl acetate = 10:1) to obtain 3.6 parts of the desired compound.

The r, R, NMR data of the compound were analyzed as shown in Nido 1lld (
It is.

1, Rν(ci-') 1760.1710,1631J, 127(1,120
ONMRCC14) IJ (11111) 1.25
(31(), 1.70(3K), 1.85(3M).

1.5-2.4 (4f-1), 4.10 (2H)
.

4.66 (21(), 4.8-5.0(21().

5.20 (1)1), 5.70 (1)1), 5
．． 95 (1) I).

6.6-7.5 (4H) Fruit Chiaysu 2 CH,C)I.

[Ethyl 8-(2-methyl-4-arya-enoxyacetyloxy)-5,9-dimethyl-deca-2,4,
9-trienoate] Synthesis Example 1 (1-4), 2.4 parts of 2-methyl-4-chloro-phenoxyacetyl alide was substituted for 2,4-dicalphenoxyacetyl acetyl alide. Other than adding (engineering, implementation? lJ
1 (1-4) and was cleaved to obtain the predetermined chemical composition vIJ43.5 m'. 1. of the compound. R,NM
R spectrum data 9X is as shown below.

1, Rν(Cm-') 176(1,171(1,l630.1270.117
(ONMR (CCJ4) δ (vomit) 1.25 (3) (), 1.70 (31 (), 1,8
3(3)1).

1.5-2.4 (4H), 2.20 (3) in.

4.1 tl (2H), 4.56 (2H).

4.8~5.0 (21(), 5.20 (1)1
).

5.63 (LH), 5.90 (IH), 6.50 (IH
).

6.9-7.5 (3E(+ Example 3 <Ethyl 8-(2-(2-methyl-4-chloro-7-dinoquine)propylene-diluoquine J-5,9-dimethyl-deca-2, In (1-4) of Synthesis Example of 4,9-1 lienoate, 2-(2-methyl-4-lyanoate) was used instead of 2,4-dicucluphenoxyacetyl chloride. ) Bukubioniruku O Ride 2
．． (+-4) of Example 1 except for adding 5611S
The reaction was carried out in the same manner as above, and 63.5 parts of the desired compound was obtained. I, R of the compound.

The NMR spectrum data are as follows.

1, Rν(c++t-') 1760.17+0.1630,1270,119ON
MR(C(J4)δ(solution) 1.25(3H), 1.60(3)1), 1.70(3
)i).

1.85 (3H), 2.20 (3) ().

1.5-2.4 (4H), 4,10 (2H).

4.66 (11(), 4.7~5.0(2)i)
.

5.0~5.3(11(), 5.(1+6(If()
.

5.90 (l) I), 6.50 (IH).

6.9-7.4 (3H) Example 4 Synthesis of [Methyl 8-(2,4-dicalphenoxyacetyloquino) 5+9-dimethyl-deca-2,4,9-trienoate] Example 1 ( t-4) In VL, methyl 8-human cuxo 5,9-dimethyl-deca-2,
Example 1 using 1-2.24 parts of 4,9-trienony
React and load in the same manner as in (1-4) to obtain the predetermined compound 7.
3.0g was obtained. 1. of the compound. The R, NMR spectra were as follows.

I, Rp (knee 1) 1760.1710.1630.1270.119ON
MR (CC1,) δ (blue) 1.70 (3H), 1.85 (3H).

1.5-2.4(4)1), 3.60(31().

4.66(,2H), 4.8~s, (1(2Fl)).

5.20 (I)i), 5.70 (114), 5
．． 95 (IH).

6.6-7. F) (4H) Example 5 CH2O)i.

[Methyl 8-(2-methyl-4-lya-phenoquinacetyloxy)-5,9-dimethyl-deca-2,4,
Synthesis Example 4 of 9-trienoate) at 2,
The reaction was carried out in the same manner as in Example 4, except that 2.4 parts of 2-methyl-4-chlorophenoquine acetyl chloride was added instead of 4-dichlorophenoxyacetyl chlorite.
The mixture was polished to obtain 3.5 parts of a given compound.

1. of the compound. R, NMR spectrum data are as follows.

I, Rv (clrL-') 1760.1720.1640,1270,118ON
MR(C(J,)δ(騨) 1.67(3H), 1.83(3H).

1.40-2.3f1 (4M), 2.23<3M).

3.67 (3H), 4.53-4.60 (2) 1)
.

4.90 (2H), 5.1 3 (IH), 5.
70 (IH).

5.95 (IH), 6.5-7.5 (4M) Example 6 CH,OH3 exposure (8-(2,4-dicumylphenoxyacetyloxy)
-5,9-dimethyl-deca-2+4+9 1'lienoic acid] In (+-4) of Example 1, 8
-Human axy-5,9-dimethylterate-2.4.9-
Using 2.1 parts of trienoic acid, (1
The reaction was carried out in the same manner as in -4) to obtain 93.0 parts of the desired compound. 1. of the compound. R.

The NMR spectrum data were as follows.

1, Rv<Sue 1) 3400~2600, 1760.1710°1630,
120O NP, 4R (CD (J,) δ (helmet) 1.67 (6H
), 1.65-2.30 (4H).

4.67(2)i), 4.93(2)1), 5,17(
1)i).

5.83-6.20 (3H), 6.67-7.33 (4H)
H)-A Example 7 8- (2,4-dicumylphenoxyacetyloxy)
Synthesis of 519-dimethylether-2.4.9-trienoic acid sodium salt 1o To 93.97 parts of the compound synthesized in Example 6 was added 0. 100 parts by volume of a 1N NaOH aqueous solution was placed in a container, and the dissolved soaking water was evaporated to dryness to obtain a predetermined compound 4.1.

Implementation ψj8 8- (2,4-dicalphenoquinoacetylon)
-5,9-Dimeirude Force -2.4.9-1 Synthesis of Lienoic γ Side Imp a Pyr'r Monium Salt 11 The compound g3.97s synthesized in Example 6 was mixed with ethyl acetate I
Dissolve in 4i parts of fJ volume and add Improvylamine (1,0
Add 59 parts. After the reaction, ethyl acetate was distilled off to obtain 4.0 parts of the desired compound.

Example 9 CH, CH.

1 Synthesis of [ethyl 9.10-dipoxy-8-(2,4-dicumylphenoxyacetyloxy)-5,9-dimethyl-deca-2,4,9-1lie/ate] of Example 1 Compound 43 synthesized in (1-4). Dissolve 1 part of t in 20 parts by volume of methylene chloride, and add 1.4 parts of perbenzoic acid to methylene chloride (40 parts by volume) while cooling with water.
Add liquid. After addition, stir overnight at room temperature. After the reaction, wash with saturated KJ hydrogen carbonate water bath solution, 10% hydrogen sulfite solution, +1 um water hemorrhoid solution, and then saturated sodium carbonate water bath solution. If Kinoso is dried with anhydrous sodium sulfate, the pressure is reduced to several Φ. Soak the product in a gel column a
A shell was prepared using a Madograph to obtain 121.7 parts of the desired compound. I, R, NMR spectral data of the compound are as follows.

1, Rv (cIn-') 1760.1710.163fl NMR (CC14) δ (4) 1.20 (3H), 1.25 (3) f), 1.71 J (
3H).

1.5-24 (4) 1), 3.20 (2) 1).

4.10 (2H), 4.65 (2H), 5.1
5 (IH).

5.90 (1l-1), 6.5-7.4 (5H) conducted 1j10 CH, CH.

(8-(2,4-dichlorphenol 1,000 cyase, 1,000 Luoyan)
Synthesis of Example 1 (1-4) of VC8 in place of compound 3
-Hydrotin-5,9-dimethyl-deca-2,9-genoic acid (2.1 parts), Example 1 (1-4)
The reaction was carried out in the same manner as above to obtain 134.0 parts of the desired compound.

The i, R, NMR spectral data of the compound are as follows.

1, Rν (α″1) 34i10~2600.176 (1,1710,120
ONMR (CC4) δ (婢) 0.9 (1 (3H), 1.0~1.77 (5H
hmm.

1.67 (3) 1), 1.80-2.20 (2H).

4.60<2K), 4.87 (2H), 5.13 (IH
).

5.76(1)(), 6.63-7.33(4H).

9.33 (If()':A Example 11 8 (2,4-dicalphenoxyacetyloquine)
Synthesis of -5,9-dimethyl-deca-2,9-genoic and sodium salt 14 Compound 13 synthesized in Example 10 3.99 parts KO0I
N NaOH water bath Qloogn portion was added, the dissolved water was evaporated to dryness, and the predetermined compound v! 14, 1 copy was obtained.

Example 12 8- (2,4-dichlorophenoquine acetylon)
Synthesis of -5,9-dimethyl-deca-2,4-genoic andimbubylammonium salt 15 133.99 parts of the compound synthesized in Example 10 was dissolved in 10 parts by volume of ethyl acetate, and 0.5 parts of inpropylamine was dissolved. (15
Add 9 parts. After the reaction, ethyl acetate was distilled off and the desired compound 4. I got Os.

Example 13 Synthesis of [ethyl 8-(2,4-dicumylphenoxyacethyloxy]-octa-2,4-genoate] In (1-4) of Example 1, instead of compound 30,
Bimanual 8-human axyocta-2,4-genony)
Using 1.84 parts, the reaction was carried out in the same manner as in Example 1 (1-4) to obtain 162.5 parts of the desired compound. 1. of the compound. The R, NMR spectrum data were as follows.

1, Ry (cWL-') 1760.1710, 1630.120ONMR (CC
/,) a (Sir) 1.27 (3H), 1.30-2.20 (41 ().

3.95-4.3'0 (4H), 4.63 (2) ().

5.50~6.25 (3fi), 6.50~7,6
7(41()) Example 14 e17 Synthesis of [ethyl 8-(2,4-dicumylphenoxyacethyloxy)-octa-,2-ethyl/ate] (1-4>VC in Example 1) , Compound 30 was replaced with dithyl 8-hydroquine octa-2-en/ate 1.8
Using 6s, the reaction and purification were carried out in the same manner as in Example 1 (1-4) to obtain 972.6 parts of the desired chemical compound. 1. of the compound. R
, NMR spectrum data were as shown below.

1, Rν (cm-') 1760.1710, 1650.120ONMR (CC
J4) δ (PP) pl, 27(3I(),
1.25-1.85(6)I).

1.85-2.35 (2M), 3.83-4.27 (4
H).

4.61) (2H), 5.67 (1M).

6.53-7.33 (4)i) Example 15 CH.

Synthesis of [dityl 4-(2,4-dicumylphenolic acid noacetyloxy)-5-methyl-hexa-2,4-genoate] Ethyl 4-human a+ne 5-methyl-hex-2,4-genoate 1 .7 parts of triethylamine, 1.11 parts of benzene (24 parts) were mixed with 2.63 parts of 2,4-dichloride and 7 cetylchloride while cooling with water. After adding fA, stir at room temperature for about 4 hr. After the reaction, water is added and extracted with ether. After drying the M layer over anhydrous sodium sulfate, it was concentrated under reduced pressure, and the product was purified using a silica gel column chromatograph (Wakogel C-200
The product was purified with molten benzene:ethyl phosphate (10:1) to obtain 182.0 parts of the desired adduct. 1. of the compound. R,NM
The R data was as follows.

1, i(ν(cm-') 1750.1?10,1640.130ONMR(C(
J4) δ(-); 1.3.0 (3M), 1.50 (6H),
4,23 (2)I).

4.66 (2I(), 6.5-7.4 (5U) Example 16 Synthesis implementation of CH3 [methyl 4 (214-dicumylphenothenacetyloxy)-5-methyl-hexa-2,5-genoate] In Example 15, (·ethyl 4-human a-1′) 5-
In the same manner as in Example 15, anti-S
6. Made from silk to obtain 193.0 parts of the specified chemical compound. 1. of the compound. R, NMR spectral data were processed as follows (
Met.

I, Ry (cm-'); 1760.1720, 1650.1260, 119ON
MR(CCl,) d(1'l") ;1.7fJ(
3H), 3.70 (31(), 4.67 (2H).

4.80(IH), 5.00(2)i).

5.6-60 (2) 1), 6.5-7.4 (31 ()
Examples 17-28 Each of the compounds synthesized in Examples 1-6, 9, 10.13-16, 12.5 parts of water and 1 part of acetone
In addition to 2.5 parts of the mixed solution, 5ORP is added as a fixing agent.
A mixture containing 0.013 parts of OL 2680 (Toho Chemical Fissure) was applied to the stems and leaves of Himedion, Mehimba, Plantain, and Hemasuke, which had been cultivated in advance. A withering experiment was conducted by visually observing the withering in the valleys.

The degree of withering two weeks after treatment is shown in Table 1v. Xun stillborn,
In other words, as an index to express the degree of wilting, 0 indicates a healthy haba, and 1 indicates that the whole hapha is wilted. This is expressed using the so-called 6-step method, which divides the dead and dead state into 5 equal parts and displays the intermediate state.

Table 1 Examples 29 to 43 o and o s parts of each of Compounds 4 to 17 and 19 synthesized in Examples 1-14 and 16 were added to 12.5 parts of water, 12.5 parts of 77 tons, acetone tz, and 5 fJ In addition to the mixed ga,! J! , VC spreading agent 5ORPOL 26800)0
．． A mixture of 0.013 parts and 0.013 parts was cultivated in advance.

After spraying the foliage of rice and corn at a treatment amount of 100 &/10 a, cultivation continued and the degree of withering of each plant was observed in the same manner as in Example 17. The degree of mortality two weeks after the treatment is shown in Table 2.

Table 2 Examples 44-51 0.005 parts of each of the compounds synthesized in Examples 1.2.4-6.13.15 and 16 were mixed with 12.5 parts of water and 1 part of acetone.
2.5@f) In addition to the mixed solution, add 5O as a spreading agent.
Willow knotweed, Sanae knotweed, pigweed, which were cultivated in advance with a mixture containing 0.013 parts of RPOL 2680.
Shaza, Inubini.

Takanapuro, 100j'7 on the stems and leaves of Hinataijikonochi
After spraying to a treatment amount of 10a, cultivation continued and the degree of withering of each plant was observed in the same manner as in Example 17. Table 3 shows the degree of mortality two weeks after the treatment.

Shigeru 3 Example 52 0.038 parts of the compound synthesized in (1-4) of Example 1 was added to a mixed solution of 300 parts of water and 300 parts of acetone, and further 0.3 parts of 5oapoL26800 was added as a spreading agent. Hifujio/ is a mixed liquid and is approximately 501 cm tall. 25 ji/l Oa on the stems and leaves of willow knotweed, purslane, and itabu
After spraying to achieve a treatment amount of 1,000 yen, the cultivation was continued and the growth of the soybeans was observed with the naked eye. As a result, 30 days later, Tae also received hifudion. Willow knotweed, purslane.

All of the dogbarrows stopped growing at the height of 4 o'clock (approximately 50 cm), and the medium buds had a large number of buds. grow, 3
After 0 days, Himezion will have 120 ki, and Yanagitade will have 90 ki.
c! rL, Purslane grew to 90cm long, and Inubini grew to 80cm high.

゛(snake)

Claims (3)

[Claims] (1) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・( I
) {However, in the formula, X^1 to X^4 are the same or different, and at least one of them is a formula▲There is a mathematical formula, chemical formula, table, etc.▼
Here, Ar is a halogen atom, a cyano group, a nitro group, a lower alkyl group, a formula -OR^9 (R^9 is a hydrogen atom, and the number of carbon atoms is 2
-10 acyl group, or a halogen-substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, which may contain at least one atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. )
A group represented by the formula -SR^■ (R^■ is defined in the same manner as above), and a group represented by the formula ▲ Numerical formula,
There are chemical formulas, tables, etc. ▼ (R^1^0 and R^1^1 are the same or different and are hydrogen atoms or hydrocarbon groups with 1 to 10 carbon atoms, may cooperate with each other to form a ring.) is a substituted or unsubstituted aromatic hydrocarbon group by at least one group selected from the groups represented by; R^7 and R^8 are the same or different, Hydrogen atom, halogen atom, cyano group, nitro group, lower alkyl group, group represented by the above formula -OR^9 and the above formula -SR
It is any group represented by ^9; n means an integer of 1 to 10. ], and other X^
1 to X^4 are hydrogen atoms or lower alkyl groups; R^
1 to R^5 are the same or different, and are a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted and unsubstituted lower alkyl group, a lower alkenyl group, and the above formula -OR^9, -SR
^9, ▲There are mathematical formulas, chemical formulas, tables, etc. It is any of the groups shown by ▼; R^■ is the formula -OR^1^2 (however, R
^1^2 is a hydrogen atom, or a hydrocarbon group having 1 to 15 carbon atoms that may contain at least one atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. ), formula -SR
^1^2 (However, R^1^2 is defined in the same way as above.) and any of the groups shown in the above formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼; k is from 0 to 15 It is an integer, l is 0 or 1, and m means an integer from 0 to 10. } Compounds represented by and their functional salts α, β-
Unsaturated carboxylic acids. (2) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・( I
) {However, in the formula, X^1 to X^4 are the same or different, and at least one of them is a formula▲There is a mathematical formula, chemical formula, table, etc.▼
Here, Ar is a halogen atom, a cyano group, a nitro group, a lower alkyl group, a formula -OR^9 (R^9 is a hydrogen atom, and the number of carbon atoms is 2 to 1
0 acyl group, or a halogen-substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms which may contain at least one atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. )
A group represented by the formula -SR^9 (R^9 is defined in the same manner as above), and a group represented by the formula ▲ Numerical formula,
There are chemical formulas, tables, etc. ▼ (R^1^0 and R^1^1 are the same or different and are hydrogen atoms or hydrocarbon groups with 1 to 10 carbon atoms, R^7 and R^6 are the same or different, hydrogen Atom, halogen atom, cyano group, nitro group, lower alkyl group, group represented by the above formula -OR^9 and the above formula -SR^
9; n means an integer of 1 to 10. ], and other X^1
~X^4 is a hydrogen atom or a lower alkyl group; R^1
~R^5 are the same or different, hydrogen atom, halogen atom,
Cyano group, nitro group, substituted and unsubstituted lower alkyl group, lower alkenyl group, and the above formulas -OR^9, -SR^
9, ▲There are mathematical formulas, chemical formulas, tables, etc.▼; R^6 is the formula -OR^1^2 (however, R^
1^2 is a hydrogen atom, or a hydrocarbon group having 1 to 15 carbon atoms that may contain at least one atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. ), formula −SR^
1^2 (However, R^1^2 is defined in the same way as above.)
and any of the groups shown in the above formula ▲There are mathematical formulas, chemical formulas, tables, etc.; k is an integer from 0 to 15, l
is 0 or 1, and m means an integer of 0 to 10. } Compounds represented by and their functional salts α, β-
A herbicide containing at least one selected from unsaturated carboxylic acids as an active ingredient. (3) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・( I
) {However, in the formula, X^1 to X^4 are the same or different, and at least one of them is a formula▲There is a mathematical formula, chemical formula, table, etc.▼
Here, Ar is a halogen atom, a cyano group, a nitro group, a lower alkyl group, a formula -OR^9 (R^9 is a hydrogen atom, and the number of carbon atoms is 2
-10 acyl group, or a halogen-substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms, which may contain at least one atom selected from an oxygen atom, a sulfur atom, and a nitrogen atom. )
A group represented by the formula -SR^9 (R^9 is defined in the same manner as above), and a group represented by the formula ▲ Numerical formula,
There are chemical formulas, tables, etc. ▼ (R^1^0 and R^1^1 are the same or different and are hydrogen atoms or hydrocarbon groups with 1 to 10 carbon atoms, may cooperate with each other to form a ring.) is a substituted or unsubstituted aromatic hydrocarbon group by at least one group selected from the groups represented by; R^7 and R^8 are the same or different, Hydrogen atom, halogen atom, cyano group, nitro group, lower alkyl group, group represented by the above formula -OR^9 and the above formula -SR
It is any group represented by ^9; n means an integer of 1 to 10. ], and other X^
1 to X^4 are hydrogen atoms or lower alkyl groups; R^
1 to R^5 are the same or different, and are a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted and unsubstituted lower alkyl group, a lower alkenyl group, and the above formula -OR^9, -SR
^9, ▲There are mathematical formulas, chemical formulas, tables, etc.▼; R^6 is the formula -OR^1^2 (however, R^1^2 is a hydrogen atom or an oxygen atom, A hydrocarbon group having 1 to 15 carbon atoms that may contain at least one atom selected from a sulfur atom and a nitrogen atom), formula -S
R^1^2 (However, R^1^2 is defined in the same way as above.) and any of the groups shown in the above formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼; k is 0 to 15 l is an integer of 0 or 1, and m is an integer of 0 to 10. } Compounds represented by and their functional salts α, β-
A plant growth regulator containing at least one selected from unsaturated carboxylic acids as an active ingredient.