JPS58189178A - N-substituted dicarboximides and herbicides containing them as active ingredients - Google Patents

Abstract

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

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to special penta-substituted dicarboximides and herbicides containing them as active ingredients.

It has been known that N-substituted dicarboximides have excellent herbicidal activity, but slight modifications to their structures (type of substituent, number 1 position, etc.) may affect the presence or absence or strength of herbicidal activity. In many cases, there are marked differences in selectivity, etc.

It is difficult to predict the herbicidal activity or selectivity of a new compound based on mere chemical structural similarity.

The inventors conducted intensive research to provide N-substituted dicarboximides with superior herbicidal activity and crop safety.
Atom or halogen atom - Water atom - halogen atom, 1 methyl group has a methoxy group at -≠ position, %
We have discovered that novel N-substituted dicarboximides, which are phenyl groups having a foot substituent, exhibit excellent performance as a compound.

The gist of the present invention is general formula Of the 7 types.

The symbol indicates a 2X atom or a -Cmi.

Engineering represents a hydrogen atom, a halogen 1L methyl group or a metmody group, and Y? and 2 are the same = are the same! Indicate the water X atom or halogen atom.

U and ■ are mutually the same or different groups represented by i+, cOB: halogen!
Alkoxy group: substituted with an alkoxycarbonyl group or a cyano group; An optionally substituted alkenyl group: Alkynyl group: Indicates a group represented by 1+ or an alkylsulfonyl group.

In the upper Ef substituent.

R1 represents a hydrogen atom, an alkyl group or a phenyl group -
Rn represents a hydrogen atom or a methyl group.

2 is an integer from 1 to 6! Show y.

Indicates the group.

Group=1 Alkyl group optionally substituted with a halogen atom: Alkenyl group: Indicates an aryl group or a hydrogen atom optionally substituted with a halogen atom.

Among the above substituents.

Upstream are hydrogen atoms, alkyl groups, and alkenyl groups.

Alkynyl group, cycloalkyl group-aryl group.

R1! 103-00D represents an aralkyl group or a group represented by 1.

R4 represents an alkyl group.

Rs and R6 are hydrogen atoms that are the same or different from each other,
Alkyl group, alkoxy group, alkoxyalkyl group, alkenyl group, alkynyl group, aryl group-aralkyl group, cycloalkyl group.

12 Alkylsulfonyl group also expressed as %i 1 -C
1-COD represents a group, or R1 and R6 represent a compound X group which may contain an oxygen atom together with the nitrogen atom in the formula.

R7 represents an alkyl group optionally substituted with a halogen atom: an alkenyl group or an aryl group optionally substituted with a halogen atom.

Rh1 represents Y, an alkyl group, a cyclotylkyl group, an aralkyl group, or an aralkyl group.

? represents an alkyl group or an aryl group.

R1 and Ru are the same or different alkyl groups.

Indicates a radical which may be substituted with an alkoxy group or a halogen.

In the *substituent above- R-cho 1 indicates a water atom or an alkyl group.

D represents a hydroxyl group, an alkoxy group, or an amino group which may be substituted with two alkyl or alkenyl groups.

N-substituted dicarboximides represented by t
It is found in herbicides as active ingredients.

Next, the present invention will be specifically explained.

The N-substituted dicarboxamide used as a herbicide in the present invention is represented by the general formula [I]. Preferably, it is represented by the general formula [n]. In the formula, M represents a nitrogen atom or -(IJ!-Y, X represents a hydrogen atom, a halogen atom such as a fluorine atom, a salt atom, an Oku! atom, a methyl group or a methoxy group, and Y and 2 represent a hydrogen atom. or a halogen atom such as a fluorine atom, a salt atom, or an odor X atom; 10 and V are the same or different from each other;

x Bi is a hydrogen atom, C1%C, the alkyl Go playing machine is C
1%G, more preferably an alkyl group from C1 to a phenyl group, Rt is a hydrogen atom or a methyl group, n is an integer of /, preferably an integer of A, and B Is it 10Rsi KC? -R”4: Water
i child-CI% C3I! +, )7 h # is an alkyl group of C1 to C, more preferably C1 to C
Hf') Alkyl group + C8-C, alkenyl group, preferably 08-C4 alkenyl group, Cx-C1 alkynyl group, preferably C, -C4 alkynyl group.

C3 ~ (B, , shift; alkyl Go is preferably “s-”)
Schiff of q: an aryl group such as an alkyl group or a phenyl group.

IJ 7ralkyl group such as benzyl group, or a group represented by 1-〇3COD (wherein -Ru is a hydrogen atom or C1-C
D is a hydroxyl group, preferably a C1-C4 alkyl group, and D is a hydroxyl group -C, -04 alkoxy group.

, -aR' In the formula, -R4 represents an alkyl group of C1 to CM (preferably C1 to C))/R'' or -N (in the formula, Hz and R4 are the same or different in tone) -C1 - one alkyl group, preferably C
An alkyl group of 1 to Cto, more preferably C1-Cm! an alkyl group of 01 to C11, preferably an alkoxy group of C
, C, alkoxyalkyl group, more preferably C1-C4 alkoxy'/M-Cx-C, alkoxyalkyl group, preferably C2-Q alkoxyalkyl group, preferably C;-C4 alkoxyalkyl group.

08-08 alkenyl group, preferably C-Cl alkenyl group, C2-C8 alkynyl group, preferably C1-CI
C8 alkynyl group, aryl group such as phenyl group, aralkyl group such as benzyl group, 03-0□ 7-chloroalkyl group, preferably Cs%C, cycloalkyl L-Cz-C
The alkylsulfonyl group of 8 has the same meaning as t'TtL)
'It represents a nitrogen atom in the formula, or 1 represents a 7-membered heterocyclic group, preferably a 7-membered heterocyclic group which may contain an FX atom; at r~7 represents a negative saturated heterocyclic group; [represented by a group represented by ]: a chlorine atom such as a chlorine atom or a chlorine atom, preferably a chlorine atom, and an alkoxy group of 01 to C4.

77 group, and an aryl group that may be substituted with a halogen atom such as a chlorine atom, preferably an alkyl group of 01 to C@ that may be substituted with a substituent such as a phenyl group, preferably an alkyl group of O, -C4 ;1 or C)~C,
1-Cφ alkenyl group optionally substituted with C alkoxycarbonyl group or cyano group, preferably C8-C
4 alkenyl group; Ct to C-numbered furkynyl group, preferably 0. ~C4 alkynyl group "-Lx [wherein, R is -R1 (wherein, By is C, which may be substituted with 1 to 3 halogen atoms, preferably a fluorine atom or a chlorine atom] Alkyl group of C, preferably %@0
1% Cs alkyl group, C: ~Cs alkenyl group, preferably CS/~C4 alkenyl group, or aryl group optionally substituted with a halogen atom such as chlorine atom, preferably phenyl group)- "@(expression 'P-"k@
('1~Cu') 7 to 'fk base go game <'a@
An alkyl group of C1 to Cs, a cycloalkyl group of Cj-C, preferably a 7-chloroalkyl λ group of C1 to Cs.

C, to C aralkyl group, preferably benzyl group.

or a 7-aryl group such as a phenyl group).

-8R9 (wherein Re is a C1 to C6 alkyl group, preferably a C1 to C4 alkyl group, or an 04 alkyl group such as a phenyl group, preferably a C1 to C heavy alkyl group).

01 to C4 alkoxy group, preferably a C,4C alkoxy group, or an aryl group optionally substituted with a halogen atom such as a chlorine atom 11. <represents a phenyl group] or a C□-04 alkylsulfonyl group or a C1-C8 alkylsulfonyl group tt. .

The compound represented by formula (I) of the present invention may optionally exist in isomers such as isomers or diastereomers. In many cases - skeleton isomers are obtained as a compound containing all isomers. These isomers can be obtained using nine known methods (
For example, various chromatography methods such as asymmetric synthesis, asymmetric synthesis using tk1 and lI materials possessed by asymmetric carbon sources, optical spectroscopy, column chromatography, thin layer deposition, and high performance liquid chromatography. It is also possible to obtain each isomer V by using the following reaction formula using each raw material.

h) (In the above reaction formula, Mu, Engineering, Y and 2 are the same as above and -11Y
The above one-component reaction is carried out in a solvent such as acetic acid, ethanol, ethyl acetate, benzene, toluene, etc., in the presence of a catalyst such as palladium or Raney nickel, under normal pressure, 0%/1% pressure, etc.
j Performed at 0°C.

(7) (In the above ffi formula, A, X-Y-z, rs*, and ■ have the same meanings as above!, and v' and U' are groups represented by 1, 2, ÷?+nC0B: /″-rogen atom-z alkoxy group-cyano group and) alkyl optionally substituted with a substituent selected from aryl group optionally substituted with 1*gen atom-!&: Alkenyl group: alkynyl group or alkyl Indicates a sulfonyl group, QGi Yaguchihegen atom or optionally an alkoxy group such as mezilad-toshite, methoxy group or nidoxy group,
(C%, along with U, indicates katanihydro or mixed anhydride).

Dioxane,] IN, IN-dimethylforfamide.

M, H-dimethylacetamide, dimethylsulfoxide, sulfolane, benzene, toluene.

Xylene, cumene-chlorobenzene-dicoolinzene, methylene chloride, lye + chlorum.

Sodium acetate, potassium bicarbonate, sodium hydroxide in a solvent such as carbon tetrachloride, trichloride, ethyl acetate, ethyl methyl ketone, ether, diisopropyl ether, etc.

Potassium carbonate, sodium hydroxide, hydroxide power 1.) Rum, barium hydroxide, calcium hydroxide.

Sodium metal, Potassium 4iL, Puttrium hydride, Potassium hydride, Flium amide,
IJ thium chloride, sodium filtrate potassium chloride, magnesium chloride, zinc chloride, iron chloride (■), iron chloride (■
), copper(I) chloride.

-Copper chloride (■), lithium iodide, sodium iodide.

Potassium iodide - potassium fluoride, cesium fluoride.

Copper oxide, calcium chloride, barium oxide.

Iron oxide (IL), iron 51 (■), lead carbonate, pyridine.

Crimson-dimethylaminovinodine, triethylamine, N
, M.-diethylaniline, benzyl F-limethylammonium chloride (promide).

PENCILTO IJ Etherammonium chloride (bromide)-tetra n-butylammonium bromide (:l-cyto), crown ethers: in the presence or absence of polyoxyethylenes, etc. -20 to λjO°C, preferably 0 to
It should be done at 200℃.

(In the above reaction formula, M, U and V have the same meanings as above,
Others are the same as above, and X'.

At least one of y/ and 2' is a hydrogen atom, the others are paired with U
This reaction has the same meaning as Y and 2).
Five Rohol Chloride Charcoal Wings.

Chlorine in solvents such as benzene and coolbenzene.

Odor 1 [sulfuryl chloride, M-ri; rusuccinidide 1M
-Noxogenizing agent such as boom succinimide t, -7σ
~ljO°C preferably -20~! The reaction is carried out at 20°C. .

(In the above reaction formula, 1. mu, X, Y, Z, RL, pancreatic and n
41 The above E same Ilt is shown, tl and V represent a hydrogen bastard, an alkyl group, an alkyl group or an alkynyl group, and B
-oxs--8R4 or S-- -methanol, water-
Hydrochloric acid, sulfur lI in a solvent such as ethanol, water-dioxane, etc.
(It) LM=
dimethyl lumamide 1M-methyl-2-pyrrolidone,
Swimming lithium in a solvent such as Ko@, Otsu-collidine, ;, 1-lutidine-pyridine.

Lithium bromide, 1" lithium iodide, 1" lithium iodide, 5% lithium iodide, etc. are carried out at 10 - 00°C: (■) Water, water-methanol, water-ethanol-water-diochitin, water-acetone, etc. In the melting plate - sodium hydroxide, water-glazing potassium,
After the reaction, the reaction is carried out in the presence of lithium, etc., in a solvent, and the residue is reacted with vinegared rice, diluted diluted hydrochloric acid, and a solvent such as dioxane at 9sO to 200°C.

(In the above reaction formula, M, X, ', Z, R1, R
"O and n have the same meanings as above, U and V represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl thickness, and B represents -0R1, -8R4 or sn,,v -w-"-"hl The above reaction may be carried out without a solvent or in a solvent such as benzene, toluene, methylene chloride, chloroform, carbon tetrachloride, tetrahydrofuran, dioxane, ether, acetonitrile, pyridine%N,N-dimethylformamide, etc. Danke,
Sulfuric acid, phosphorus & methanesulfonic acid, p-toenesulfonic acid/acid, thionyl chloride, phosphorous oxychloride.

Sodium hydrogen carbonate, potassium hydrogen carbonate in the presence of methyl chlorocarbonate, ethyl chlorocarbonate, N,M'-dicyclohexylcarbodiimide, etc.

Sodium carbonate 1Jum potassium monopodate-sodium hydroxide,
Potassium hydroxide, pyridine, triethylamine, N, N
-In the presence or absence of a base such as diethylaniline-
It is carried out at a temperature of 0°C to iso°C.

Rubonic acids may form various intermediates such as fermented products, acid anhydrides, and mixed acid anhydrides.

Target compounds are produced by reacting with various alcohols, mercaptans, amines, etc. It is also possible in some cases to use these intermediates f;tjIL separately.

(6) Engineering (upper F, anti-E formula, A-x, x-z, R1-R2
゜n and 8 have the same meanings as above, [i and V represent a hydrogen atom or an alkyl group, Q represents a halogen atom such as chlorine, bromine, and iodine, or mezilad-toshisheet, etc.] The above reaction is Acetone-Ethyl Mether The compound of the present invention thus obtained can be used as a herbicide as is, but it is usually mixed with an inert liquid carrier or solid,
A suitable surfactant and the like are added to this and used in the form of an emulsion, one powder, one tablet, an irrigant, etc.

Liquid carriers include toluene, xylene, methylnaphthalene, cyclohexane, butanol, glycol, dimethyl sulfoxide, dimethylformamide, acetone,
Medel isobutyl, animal and vegetable oils, fatty acids, fatty acid esters.

Solid carriers include clay, kaolin clay, Melk, bentonite, and quartz clay.

Examples include silica, calcium carbonate, and vegetable powders such as soybean flour and wheat flour. In addition, if necessary, other active ingredients such as 1 agricultural film, 1 insecticide, nematicide or other herbicide, 1 set of plant growth regulators, soil conditioner and fertilizers.
It can also be used in combination with departments. In addition, in order to obtain a real weeding effect, supplements such as spreading agents, emulsifiers, wetting agents, and fixing agents may be used. ? 4 as appropriate (may be mixed.

The N dose of the cooling agent of the present invention is determined by m
! Although it varies depending on the situation such as the miscellaneous electrical appliances to be treated, the time of treatment, the treatment method, and the quality of the earthworks, it is in the range of 1 to 1500 yen as the essential income.

The heather invention ζ's irritant remover is effective against the germination of the ridges during the transfer of water.
It can be used for either S treatment or first stage treatment.
There is a herbicide that exhibits strong killing activity against annual phlegmon and perennial phlegm, and has minimal effects on transplanted paddy rice, which is conventionally preferred as a herbicide for today's use.

It also showed excellent herbicidal activity against weeds and perennial weeds in 2011, with sufficient residue, and juvenile t even in 1 treatment of mixed pre-germination soil and 1 treatment of stem and leaf incense in field cultivation. Takano! It has an excellent effect that the effect on crops is extremely negative even when treated with ζ. In particular, until now existing herbicides have been considered to have little control. There are also other varieties such as Noe Morning Glory, Datura Datura, and Ichibi! ! Same as grass! Showing consideration or imitation.

The present invention is used to control the following weeds, such as wild morning glory.

Shi;za, Japanese knotweed, Datura japonicum, Iteto, Yaemugura, white mustard, wild mustard.

Chickweed leaf beetles, dogfish.

Pig beak. Onagumomi, Camille, and Kikashigusa.

Azena, Takasaburou, Tawokogi, Abu Tsume.

Chickweed, Mizomba.

Weeds that are monocotyledonous plants - for example, brown millet.

Japanese grasshopper, Japanese grasshopper;

Sivamugi, kayarigu? , Rii Kayatsuri, Kurogwai,
Matsubai, hotarui, izugayari.

Koukyagara: Nagi, Urikawa, Heraomodaka, Omodaka.

The inventive compounds can be used as selective herbicides in the cultivation of crops such as:

Cultivated crop that is a dicotyledonous species: Soybean cotton.

Tenbui, sunflower pea, potato-lily.

Domestic cultivated crops: rice, wheat.

Barley, oats, rye, corn, sugar cane.

The scope of application of the compound of the present invention is not limited to the above-mentioned types of plants, but it can also be used on other plants by the same application method.

Next, the present invention will be described in more detail with reference to Examples, but the invention is not limited to the following Examples unless the gist of the invention is exceeded.

Residue / /, Production of λ-tetramethylene-M-(j-amino-Hiro-chlorophenyl)hydantoin/, 2-tetramethylene-N-(3-nitro-chlorophenyl)hydantoin (ap13313≠°C) 3i,
Catalytic reduction was carried out at j = 40 °C in the presence of 5% palladium on carbon. After adding y-methicillolidone l5Oxlf and dissolving the precipitated crystals.

The catalyst was separated and ethyl acetate was distilled off under reduced pressure.

When the remaining N-methylpyrrolidone solution was added to water and the precipitated crystals were collected, the compound (2)-coj, 2f/ described in Table 3 was obtained.
Y: Got it. Compound (AIO) was also synthesized in the same manner.

1. Production of 2-tetramethylene-1i-[4-chloro-3-(l-dimethylcarbamoylethyl)aminophenyl]hydantoin 1.2-tetramethylene-N-(j-amino-terchlorophenyl ) A mixture of 3LOg of hydantoin 2t-O9-11bromo N-dimethylpropion dispersion amide and 10.09g of sodium bicarbonate was heated and stirred at 140°C for 3 times, cooled to room temperature, and dithyl acetate ooxttt2[I
and extracted it. After washing with water, it was dehydrated with 8-water bottle of sodium, and the solution was removed under reduced pressure. Residue t silica gel column (development.

It was purified using a solvent system of vinegared rice and ethyl nyhexane==J:/) to obtain a compound (mu2)s,igt shown in Table 3.

1%9 In the same manner as in Example 2, the compounds listed in Table 3--Dil, J
≦3-7≦, r)'i/obtained. In addition, all one compound was confirmed to have 7iM by engineering R spectrum and/or ip-MP spectrum.

Try Mfl! / Upland soil treatment test 2. Upland black soil R4 was placed in a 300-minute Noir resin vat, and after fertilization, each seed of wheat and corn was sown and covered with soil in steps 2 to 31.

MI of crabgrass, Japanese knotweed, and white grass in the surface layer of this soil r4
After mixing #7L of seedlings on Muninko 1, compound mul ~ IQ'l
ff j-(j
', ≠'-cyclophenyl) '*'-dimethylurea (hereinafter abbreviated as comparative agent M) or ko-dichlorophenyl-buta'-nitrophinyl ether (hereinafter abbreviated as comparative agent B). The active ingredient is diluted with water, and the active ingredient is 7 are and a half 91 λ-r, and the active ingredient is 5.
Spray it evenly on the ±XJI landing surface using a small power pressurized sprayer so that it is -5o. Mulberry agent dispersibility: 100g of herbicidal effect in 20 days
At the same time, we also provide 511 information on chemical damage to each crop.
I went to m1t, and it is shown in the table below.

Hat - Evaluation of weeding power =7 (chi) was calculated and expressed as a herbicidal effect value number according to the following criteria.

What about the evaluation of helmets and drug damage?

=Y()) ・Search for the following group #! It was expressed as the drug damage coefficient.

Table - Soil test f%2 Stem and foliage treatment test Field blackberry (soil is deposited on a small polyethylene center bot,
After fertilization, edible vinyl radish-0 seeds and seeds were sown in each pot.

Continuing with cultivation management in a warm environment '1, when the growth rate of the test plants reached the edible and second leaf stage, and when the daikon radish reached the first true leaf stage, an emulsion containing compounds Ml to IQtt as active ingredients was applied. and comparative agent 3. - Milk containing dichlorp C pionic acid anion IJ (hereinafter abbreviated as comparative agent 0) as an effective acid was diluted with water, and the active ingredient was 11% O1JO0-21,0. /
' 2 j '% of each v4 product M
Spraying treatment was carried out using 11 small power pressurized sprayers so that the amount of liquid was 1Qi per Iare.

After that, observations were made in the mixture, and the herbicidal effect and herbicidal damage were investigated on the jth day of the chemical application.The results are shown in the table below. It was expressed in

Table-! Test Example 3 Warm water soil treatment test before paddy field weed emergence
Paddy rice seedlings at the 10,000 and 2.7 leaf stages (Product P1: Sasanishi So simple sentence:
/ J, j cx-Seedling quality: Good>Y 2 plants 1 per pot
Insertion depth with stocks/J fi soaking! went. 3.5
The next day, the granules containing the compound ml to 10 t and 8-(2-chlorobensilt 1 t) were added.
．． A predetermined amount of granules containing N-diethyl-thiol carbamate (hereinafter abbreviated as comparative agent) as an active ingredient per 1 are/2.5-2j -j (7 g) was poured onto the flooded surface. I took it down the street.

After treatment, a water reduction of 9 jcm/day was applied for 3 days, and after 7 days, the water was kept in a greenhouse.
) A'jiEY went.

The characteristics of the imported herbicidal power and herbicidal damage σ) shown in Table 6 were expressed in the same manner as the base of the test gal.

Table-6 Applicant: San-ai Chemical Industry Co., Ltd. Agent: Patent attorney Hase Yo, 'ko and 1 other person

Claims (1)

[Claims] 10 In the general formula M, every nitrogen atom represents -CH-. (2) represents a hydrogen atom, a halogen atom, a methoxy group spanning a methyl group, and -Y36 and 2 represent the same or different hydrogen atoms or halogen atoms. Lljc' and V are the same or different water groups, represented by the following formula: halogen↓・. alkyl group optionally substituted with a substituent selected from atom-alcopolycyanyl group-cyano group and aryl group optionally substituted with a halogen atom: Al:jP cycalinyl group=or cyano group Optionally substituted alkenyl group: Alkynyl group: ! Represented by: N stone base -
1-2 Alkyl unyl group t'77f. Substitute 1,000 for the above. R1 represents a water wing atom-almonyl group or a funinyl group, 138 represents water yAJ-P or a mer group, and m: represents the number of g from 7 to 1. B is represented by 10R8, -εR4, or 7: -ni-, and represents a group. Ru:! & or Alkyl group optionally substituted with a halogen atom: Alganyl group: Indicates an aryl group or a hydrogen atom optionally substituted with a halogen atom. In the above f-fighting group. Three S is hydrogen! Child - alkyl group, alkenyl group. Alkynyl group - cycloalkyl group, arylRLt group, aralkyl group or I 1-00
D represents a stone group, R4 represents an alkyl group. Bs and Ha are hydrogen atoms that are the same or different from each other,
Alkyl group, alkoxy group, alkoxyalkyl group - alkenyl group, alkynyl group, aryl group, aralkyl group, cycloal may contain a scattering atom together with the nitrogen atom in the formula (represents a multiple X ring group. R7 is ... Alkyl group optionally substituted with a halogen atom: Indicates an alkenyl group or an aryl group optionally substituted with a halogen atom. R8 is an alkyl group, a cycloalkyl group, an aralkyl group, or an aryl group Y: Indicates. R''k''L represents an alkyl group or an aryl group. R1.? and Sha represent the same or different alkyl group, an alkyl group, or an aryl group which may be substituted with a halogen. R 1 hydrogen atom or N-substituted dicarboximides represented by the formula: hydroxyl group: alkoxy group: or /II to an amino group which may be substituted with one alkyl group or alkenyl group. (2) General formula [large width, j X, Y, Z −R', R'',
n @ and B are the same as above, ■ is Mizuyuki Rinko, an alkyl group, w (in the formula, Sancho is monologen atom and -C-
% FF claim represented by ], which represents a group represented by (represents an alkyl group) or a group represented by (in the formula, R8 represents an alkyl group) even if R8 is substituted. N-substituted dicarboximides of the scope of item 1. (3) In the general formula r. Mu is a nitrogen atom =! or -C...-. 〇 represents an unnatural atom, a halogen atom, a methyl group or a methoxy group, and Y and 2 represent different hydrogen atoms or halogen atoms. U and 7 are the same or different from each other
an aryl group which may be substituted with 9, an alkyl group which may be substituted with n substituents, a dialni7sibalbonyl group, or an alknylconialkynyl group where C may be substituted with a cyano group; Base: ! The group represented by - also -
2 represents an alkylsulfonyl group. Among the above substituents. R1 represents a water bulky atom, an alkyl group or a huniyl group,
R engineering is a water bulk atom 1 = indicates a methyl group, and n is an integer of 4! show. B! Ni03・, -εtad・, also indicates the group that is rewarded with i-Natsuku1"- E is P?, ORi, the group that is rewarded with Kita1e or <'pli or A halogen atom-substituted (good aryl group: argunyl i: halogen may be substituted with a kenme atom)-al group, and i=a hydrogen atom. The above-mentioned substituted group. Y= , 1 is 7?C elementary atom, alkyl group - alkenyl group. Alkynyl group, Schiff C alkyl group, aryl group, aralkyl group or -C3-
COD indicates a group. R4 represents an alkyl group. Rs and ? are the same or different from each other and represent a group represented by an alkyl group, an alkoxy group-alnyxyalkyl group, an alkenyl group, an alkynyl group, a -1 lyl group, an aralkyl group, or a cycloal group, or R1 and R@ are the formula Indicates a heterocyclic group which may contain an & element together with the nitrogen atom. R7 represents an alkylene group which may be substituted with a rogen atom: an alkenyl group which may be substituted with a hydrogen atom; R1 represents an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group. R' represents an alkyl group or an aryl group. 31' and Butl represent an alkyl group which may be substituted with the same or different alkyl group, alkoxy group or halogen. An N-substituted dicarboxy group represented by the following formula: Diiwater≦Nialkoxy group: indicates an amino group which may be substituted with an alkyl group or an alkenyl group from /I! A herbicide whose active ingredients are herbs.