JPS6372663A - N-benzyl-2-alkyl-2-cyanoacetamide compound - Google Patents

Abstract

NEW MATERIAL:An N-benzyl-2-alkyl-2-cyanoacetamide compound shown by formula I (R1 is alkyl; R2, R3 and R4 are H or alkyl; X1, X2 and X3 are H, alkyl, halogen, halogenoalkyl, alkylthio, alkoxyalkyl, nitro or cyano). EXAMPLE:N-alpha,alpha-Dimethylbenzyl-2-,t-butyl-2-cyanoacetamide. USE:Useful as an excellent herbicide for paddy fields, having selectively herbicidal activity, a herbicide for plowed fields, a defoliant, germination inhibitor, growth regulator, insecticide and fungicide. Stable to paddy-rice plant, gramineous crops, broad-leaved crops such as soybean, etc. PREPARATION:For example, a compound shown by formula II is reacted with a compound shown by formula III preferably in the absence of a solvent at 50-220 deg.C to give a compound shown by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The EAa of the present invention provides a novel N-benzyl-2-alkyl-2-cyanoacetamide compound.

(Prior art and problems to be solved by the invention) Conventionally, many N-benzyl-2-alkylacetamide compounds have been synthesized.
No. 5-43014 and JP-A-56-26853 describe that compounds represented by the following general formulas Z-1 and 2-2 have herbicidal activity.

CH, C1 (.

(However, X is a halogen atom, R&#'it-butyl group or t-amyl group, Rb and Re are the same or different hydrogen atoms, and Y is the same or different methyl group,
(Halogen atom or methoxy group, n represents an integer of 1 to 2.) However, when these compounds are applied as herbicides in high doses to transplanted paddy rice, or when applied to flooded and directly sown paddy rice, It had the drawback of causing drug damage that cannot be ignored.

(Means and Effects for Solving the Problems) As a result of extensive research into a series of 2-alkyl-2-cyanoacetamide compounds, the present inventors found that a series of N - Benzyl-2-alkyl-2-cyanoacetamide compounds are extremely safe not only for transplanted rice but also for paddy rice in flooded direct sowing cultivation, and have a high herbicidal effect against paddy weeds. We discovered that it is a selective herbicide and were able to complete the present invention.

That is, the present invention relates to the general formula (wherein R4 represents an alkyl group, R2, R3 and R
4 represents the same or different hydrogen atom or alkyl group, X4. X2 and X3F'i each represent a different hydrogen atom, alkyl group, halogen atom, halogenoalkyl group, alkoxy group, alkylthio group, alkoxyalkyl group, nitro group or cyano group. ) N-benzyl-2-alkyl-2-cyanoacetamide compound stone.

The compounds represented by the above general formula (1)'r are new compounds, and when these compounds are used as herbicides, they can be used in paddy fields of wild grasses, cypresses, and scallops at doses of 50 fl/10 a or less. Kills weeds and costs 1000,! It is safe for directly sown rice even when used at a high concentration of i'/10a. Thus, the compound represented by general formula (1) has high herbicidal activity,
It has two properties: excellent selective herbicidal activity.

The alkyl group represented by R1 in the above general formula (1) is not particularly limited, but generally has 1 to 6 carbon atoms.
Straight-chain or branched ones are preferred, and the most preferred examples include methyl, ethyl, propyl, and butyl groups, particularly methyl and ethyl groups. In addition, in the general formula (1), R2, R3, R4, X,
The alkyl group represented by X2 and X3 can be used without particular limitation, but generally has 1 to 12 carbon atoms, preferably 1
~6 linear or branched chains are preferred. Specific examples of the alkyl group include methyl group, ethyl group, n-
Propyl group, 110 propyl group, n-butyl group, 1so
-butyl group, t-butyl, n-pentyl group, n-hexyl group and the like.

In the general formula (1), examples of the halogen atoms represented by X, X2, and X3 include chlorine, fluorine, bromine, and iodine atoms.

In the general formula (1), the halogenoalkyl groups represented by Xl, X2 and X3 can be used without any particular restriction.

In general, those in which all or part of the hydrogen atoms in a linear or branched alkyl group having 1 to 12 carbon atoms, preferably 1 to 6 carbon atoms, are substituted with the halogen atoms are preferred. Specific examples of the halogenoalkyl group include chloromethyl group,
Bromomethyl group, fluoromethyl group, iodomethyl group,
Dichloromethyl group, dibromomethyl group, difluoromethyl group, short methyl group, trichloromethyl group, tridi10 momether group, trifluoromethyl group, chloroethyl group, bromoether group, fluoroethyl group, dikuo o
x thyl group, 7:70 moethyl group, difluoroethyl group, trichloroethyl group, triprothousethyl group, trifluoroethyl group, and the like.

In the general formula (1), the alkoxy groups represented by Xl, X2 and A book is preferred. Specific examples of the alkoxy group include methoxy group, ethoxy group, n-propoxy group, is
o-7'' lopoxy group, n-ptoxy group, t-butoxy group, n-pentoxy group, n-hexoyacyl group and the like.

In the general formula (1), the alkylthio groups represented by Preferably. Specific examples of the alkylthio group include methylthio group, ethylthio group, n-propylthio group, 1ao-propylthio group, and 1ao-ethylthio group. .

In the general formula (1), the alkoxyalkyl groups represented by Xl, X2 and A book is preferred. Specific examples of the alkoxyalkyl group include methoxymethyl group, methoxyethyl group, methoxypropyl group, ethoxymethyl group, ethoxyethyl group, n-glopoxymethyl group, 1ao-pro?
Examples include oxymethyl group.

N-benzyl- represented in the general formula (1) of the present invention
The structure of the 2-alkyl-2-cyanoacetamide compound can be confirmed by the following method.

(a) By measuring the infrared absorption spectrum (IR), a strong characteristic absorption based on the carbonyl bond of the amide group can be observed around 1700 to 1620 cm. Although the strength varies depending on the type of compound, 220
0~2280cm Near KC! ``As a typical example in which absorption based on N bonds can be observed, the infrared absorption spectrum of N-α,α-dimethylbenzyl-2-t-butyl-2-cyanoacetamide is shown in Figure 1.

←) By measuring the mass spectrum (M8) and calculating the composition formula corresponding to each peak observed (generally a number expressed as m/・, which is the ion molecular weight m divided by the number of charges of the ion), It is possible to know the molecular weight of the compound subjected to measurement and the bonding mode of each group within the molecule. That is, when a sample subjected to measurement is expressed by a general formula, the molecular ion peak (hereinafter abbreviated as Me) generally follows the isotopic abundance ratio according to the number of male atoms contained in the molecule. Since the intensity ratio is observed, it is possible to determine the molecular weight of the nine compounds by subjecting it to measurement. Further, for the compound represented by the above general formula, characteristic peaks corresponding to the following are observed, and the bonding mode of the molecule can be known.

(c) 1H-nuclear magnetic resonance spectrum ('H-NMR')
), it is possible to know the bonding mode of hydrogen atoms present in the compound of the present invention represented by the above general formula. The N-benzyl-2-alkyl 2-cyanoacetamide compound represented by the above-mentioned general formula (1) has a singlet absorption near 3.3 to 3.7 ppm based on the proton of the methine group at the 2-position. It is acceptable.

I H-NM of the compound of the present invention represented by the above general formula
FIG. 2 shows an H-NMR diagram of N-α,α-dimethylbenzyl-2-t-butyl-2-cyanoacetamide as a representative example of R (Jppm: double chloroform solvent based on tetramethylsilane). The analysis results are shown below.

(a) (b) That is, a single line corresponding to 9 protons was observed at 1.15 ppm, and can be attributed to three methyl groups (&). A single line corresponding to 6 protons was observed at 1.70 ppm and can be attributed to two methyl groups (b). 3. A single line corresponding to one groton was observed at OOppm and can be attributed to methine proton (c). A single line corresponding to one proton was observed at 6.26 ppm and can be attributed to the proton (d) of the amino group (NH).

A single line corresponding to 5 protons was observed at 7.28 ppm, and can be attributed to the proton (.)K of the benzene ring.

(b) By elemental analysis, determine the weight percent of carbon, hydrogen, nitrogen, and if it contains halogen and sulfur, each weight percent of halogen and sulfur, and further subtract the sum of the recognized weight ranges of each element from 100, The weight range of oxygen can be calculated and therefore the compositional formula of the compound can be determined.

The compound of the present invention has R11R2゜R3r in the general formula
R4*Xl* Although its properties differ depending on X2 and X3, it is generally a colorless, pale yellow, or pale brown solid or liquid at normal temperature and pressure, and tends to decompose when the temperature exceeds a certain temperature.

The compounds of the present invention include benzene, ether, alcohol,
It is soluble in common organic solvents such as chloroform, acetonitrile, N,N-dimethylformamide, and dimethyl sulfoxide, but almost insoluble in water.

N-benzyl-2 represented by the general formula (1) of the present invention
The method for producing the -alkyl-2-cyanoacetamide compound is not particularly limited, and any production method may be used. A particularly preferred manufacturing method is as follows.

By reacting the 2-alkyl-2-cyanoacetic ester represented by the general formula % formula (2) with the indylamine compound represented by the general formula, N-benzyl-2 represented by the general formula (1)
-Alkyl-2-cyanoacetamide compound is obtained. However, in formulas (2) and (3), Rll R2゜R3+
R4+ Xl + X2 and X3 are the same as above, and R
5 is the same as the alkyl group represented by R2 above. The above reaction is hereinafter referred to as reaction (1).

Mano General Formula % Formula % (4) [However, R4 is the same as above, and X represents a halogen atom. ] By reacting the 2-alkyl-2-cyanoacetic acid halognide represented by the above with the benzylamine represented by the general formula (3), N-
A benzyl-2-alkyl-2-cyanoacetamide compound is obtained. This reaction is hereinafter referred to as reaction (ii).

In reaction (1), the molar ratio of both compounds to be charged may be appropriately determined as required, but it is common to use equimolar amounts or a slightly excess amount of the benzylamine derivative.

The reaction (i) K is preferably carried out without a solvent, but an organic solvent may also be used. Examples of solvents preferably used include aliphatic or aromatic hydrocarbons such as benzene, toluene, xylene, hexane, hectane, petroleum ether, chloroform, methylene chloride, and ethylene chloride, or halogenated hydrocarbons. Ethers such as diethyl ether, dioxane, and tetrahydrofuran; Ketones such as acetone and methyl ethyl ketone; Nitriles such as acetonitrile; N,N-dimethylformamide, N,N-diethylformamide, etc.
-Dialkylamides; examples include dimethyl sulfoxide.

The temperature during the reaction can be selected from a wide range, but
Generally, it is sufficient to select from 0°C to 250°C, preferably 50°C to 220°C. Further, the reaction time in reaction (1) varies depending on the type of raw materials, but it is usually sufficient if it is selected from the range of 5 minutes to 10 days, preferably 1 to 40 hours. It is also preferable to stir the reaction mixture during the reaction.

The molar ratio of the two compounds in the reaction (ii) K may be appropriately determined as necessary, but it is common to use equimolar amounts or a slightly excess molar amount of the benzylamine derivative. Further, in reaction Gi), it is preferable to use a general KN organic solvent, and as the solvent, the above-mentioned reaction (1)
Examples include those that are equivalent to those used in

Please note that hydrogen halide is produced as a by-product in reaction (11). Since this hydrogen halide causes a decrease in the yield of the product, it is usually preferable to coexist a hydrogen halide scavenger in the reaction system. The hydrogen halide scavenger is not particularly limited, and any known one can be used.

Examples of scavengers that are generally suitably used include trialkylamines such as trimethylamine, trinib/l/humin, and tripropylamine, pyridine, sodium alcoholade, and sodium carbonate.

Reaction (if) The reaction temperature and reaction time at K can be selected from a wide range, and generally it is sufficient to select one reaction degree from the range of 0 to 200°C, preferably 50 to 150°C.

The reaction time also varies depending on the type of raw material, but is usually 30
It is sufficient to select from the range of minutes to 5 days, preferably 1 to 50 hours. It is also preferable to stir the reaction mixture during the reaction.

The method for isolating and producing the desired product, ie, the N-benzyl-2-alkyl-2-cyanoacetamide compound represented by the general formula (1) from the reaction system, is not particularly limited, and any known method can be employed. For example, in reaction (1), after distilling off the reaction solvent and excess reaction reagent from the reaction solution, and in reaction (11), after removing the reaction solvent, reaction reagent, and the salt produced, the remaining solution is distilled into chloroform. , benzene, ether, and other solvents. The desired product can be obtained by drying the organic layer with a desiccant such as Glauber's salt or calcium chloride, and then distilling off the organic solvent and vacuum distilling the residue. In addition to isolation and purification by vacuum distillation, it can also be purified by chromatography or, if the product is a solid, by recrystallization.

The compound represented by the general formula (1) of the present invention can be used for various purposes, but particularly exhibits a remarkable effect as a herbicide. For example, it is extremely safe for rice even when applied at higher concentrations than conventional herbicides for paddy fields, and is an excellent paddy field herbicide with selective herbicidal activity that kills many types of paddy field weeds. Ru.

The N-benzyl-2-alkyl-2-cyanoacetamide compound exhibits an excellent herbicidal effect on paddy field weeds, but is particularly effective in treating flooded soil before and after germination of Cyperaceae weeds, broad-leaved weeds, and perennial weeds. Shows remarkable herbicidal effect. For example, it has an excellent weeding effect on weeds that are harmful to rice fields, such as fireweed and grass weed, not only during germination but also during the growing season.
．． It is highly safe even when transplanting young seedlings at the 5-leaf stage.

The amount of the pyrazole compound to be applied to paddy fields is generally 10 are/sh, 21 to 200 (l preferably IOF to
500.9 may be used as the emotional component amount.

The properties of the N-benzyl-2-alkyl-2-cyanoacetamide compound represented by the general formula (1) vary depending on the type of substituent, but even when applied at high concentrations, it can be used not only for transplanted paddy rice but also for direct sowing. They have a common feature of being extremely safe for paddy rice. In particular, R3 and R4 in the above general formula are hydrogen atoms or methyl groups, and at the same time K
X1r Compounds in which X2 and X3 are the same or different hydrogen atoms, halodane atoms, methyl groups, and methoxy groups have a molecular weight of 1000 to 2000. ! Even at a dosage of i'/10m, it is extremely safe for direct-seeded paddy rice. Furthermore, compounds in which R2 in the above general formula is a hydrogen atom and R3 and R4 are methyl groups are characterized by having particularly strong activity against weeds of the Cyperaceae family, such as firefly, Cyperus japonica, and Cyperus japonica, in rice fields.

Examples of paddy field weeds on which the N-benzyl-2-alxy-2-cyanoacetamide compound represented by the general formula (1) exhibits herbicidal effects are as follows.

It has a particularly high herbicidal effect on weeds of the Cyperaceae family, such as firefly, cypress, and cyperus, and also has a remarkable herbicidal effect on broad-leaved weeds, especially cypress, azalea, and red pepper. It has the second highest herbicidal effect on grass weeds, but it is even better if the amount of active ingredients used is increased or if known herbicides such as amide herbicides and carbamate herbicides are used in combination. Results may be obtained. Weeds that can be particularly effectively weeded include golden weed,
Tinbie, Tibles, Kazuno Kogusa, Tamagaya, Mizuhanapi, Hinagayari, Kawarasugana, Hiri, Tenzuki, Himetenkki, Hidelico, Hidelico, Hidelico, Mizu are Yari, Himekugu, Riri O Gwai, Koukagala, Omodaka, Aginashi , Hilmushi exit, Denjisou , Japanese parsley, willow knotweed, Japanese knotweed, Japanese privet, Hoshikusa, Japanese chickweed, Japanese thrush, Kikashigusa, Kizumatsupa, Japanese japonica, Japanese clover, Japanese azalea, Japanese japonica, Japanese japonica,
These are paddy field weeds such as Japanese sagebrush, sour pepper, horsetail, azalea, and red pepper.

Furthermore, N-benzyl-2- represented by the general formula (1)
Alkyl-2-cyanoacetamide compounds have a high degree of selectivity between paddy field weeds and paddy rice, so they can be applied over a long period of time from the time of germination to the growing season of paddy rice. Moreover, the advantage that the pyrazole compound can be applied extremely safely to flooded and directly sown rice is a major feature of the pyrazole compound.

Furthermore, it has a selective weeding effect when used as a herbicide in fields, so wheat, barley, corn, etc.
It can be safely applied not only to gramineous crops such as upland rice, but also to broad-leaved crops such as soybeans, cotton, and beets.

Furthermore, since the N-benzyl-2-alkyl-cyanoacetamide compound represented by the general formula (1) of the present invention affects plant growth, it can also be used as a defoliant, a germination inhibitor, and a growth regulator. I can do it. Also, the N of the present invention
-Benzyl-2-alkyl-2-cyanoacetamide compounds can be used as insecticides and fungicides in addition to the above-mentioned uses.

N-benzyl-2 represented by the general formula (1) of the present invention
The mode of use of the -alkyl-2-cyanoacetamide compound is not particularly limited, and the mode of use of known herbicides can be used as is. For example, it can be used in any desired dosage form such as granules, powders, emulsions, wettable powders, tablets, oils, aerosols, smokes, etc. using inert solid carriers, liquid carriers, emulsifying dispersants, etc.

Of course, auxiliary agents for formulation, such as spreading agents, diluents, surfactants, and other ingredients, can also be added as appropriate.

N-benzyl-2 represented by the general formula (1) of the present invention
-Alkyl-2-cyanoacetamide compounds can be used in combination with insecticides, fungicides, other agricultural chemicals, fertilizer substances, soil conditioners, and the like.

EXAMPLES In order to explain the present invention more specifically, the present invention will be described below with reference to Examples and Comparative Examples; however, the present invention should not be limited to these Examples.

Example-1 4.309 g of ethyl 2-t-butyl-2-diatacetate, α, α-dimethylbenzylamine (4.12 g) was placed in a 50-gonase type flask and heated and stirred on a 200° C. oil bath for 3 hours.

After returning the reaction product to room temperature, it was recrystallized from chloroform-hexane to give colorless needle crystals of 1.52. ! I got i+. The IR of this material was measured and the results were shown in Figure 1.3
Absorption based on a bond to 320 crn-', 2960 c
m to C) (absorption based on bonds, 2230 cm
Absorption based on cyano bonds (CAN), 1650cWI
showed strong absorption based on the amide bond (C=O). Its elemental analysis value is C74,33q6°H8,55%
, N 10.71% Te composition formula C16H22N2
C74.3 which is the calculated value for 0 (258,36)
It matched well with 7 tou, H8, 60, and N10.84.

Also, when MS was measured, a peak corresponding to Hachinohe was found at rn/e258, rrv'a 243 K CM"-CR2
, peak corresponding to l, CH at rrv/e 119.

'H-NMR (δ: ppm: tetramethylsilane standard.

(deuterated chloroform solvent) was measured and the results are shown in FIG. The analysis results were as follows.

(a) (b) Show a single line for 9 protons at 1.15 ppm &
) was equivalent to a proton. A single line corresponding to 6 protons was shown at 1.70 ppm, which corresponded to the methyl proton in b). 3. A single line corresponding to one proton is shown at OOppm, which corresponds to the methine proton in c). 6.26ppmK
A broad single line for one 7' roton was shown, which corresponded to the amino proton in (d). 5 protons at 7.28 Ppm
A single line is shown, which corresponds to the proton of the benzene ring in (e).

The above results show that the isolated product is N-α,α-dimethylbenzyl2. It became clear that it was t-butyl-2-cyanoacetamide. The yield was 23.2 kg.

Example-2 2-t-butyl-2-cyanoacetic acid chloride (3.169%) and chloroform (7Qd) were placed in a 200Rj eggplant-shaped flask, and under ice cooling, p-isopropyl-α-methy, A/hair zylamine (4.29%), and triethylamine (3.1%) were added. 0Jt-10
A solution of 111 dissolved in chloroform was added dropwise over 30 minutes, and the mixture was further stirred overnight at room temperature. The next day, the reaction solution was transferred to a separating funnel, washed with dilute hydrochloric acid and water, dried over sodium sulfate, removed chloroform, and recrystallized from benzene-hexane to obtain 3.0 J of colorless crystals. IR of this
As a result of the measurement, at 3300m-', the absorption based on the CB bond is 2960 1K, the absorption based on the CB bond is 2240c
Absorption based on cyano bond (CmiN) in M-', 165
A strong absorption based on the amide bond (C=O) was observed at 0 cm-'. Its elemental analysis value is C75, 27%, H9
,1? It is 9.75% N and has the composition formula Cl8H26N.
C75, which is the calculated value for 20 (286,42).
47th section, H9, 17th, N9.78 were in excellent agreement.

In addition, when MS was measured, a peak corresponding to m/C286, 285 and (yP)-1), m/e 271
, 270 (M'-CH5), ((M'-x)-
peak %/@229.228 corresponding to (cH,)
yP-C4H9) + (<M'E'-1) -C4H
,) showed a peak corresponding to rrV/e 162-. The results of 'H-NMR (δ: ppm: 9-fold chloroform solvent based on tetramethylsilane) were as follows.

(c) Show a single line for nine 1.11ppmK protons a)
The protons were equivalent. 6 protons in 1.21 ppm
The double line for each individual is shown and corresponds to the methyl proton in b). A double line corresponding to three glotons was shown at 1.48 ppm, which corresponded to the methyl proton in e). 2.85 ppf
Let n denote the multiplet of one proton, which corresponds to the methine proton in d). A single line corresponding to one proton is shown at 3.07 pprn, which corresponds to the methine proton in e). 6
．． It showed a wide doublet of one 35 ppm IC proton and corresponded to the amino proton of f). 7.09 ppm
A single line for 4 K7' rotons is shown and corresponds to the proton of the benzene ring in X).

The above results indicate that the isolated product is N-p-isopropyl-α
-Methylbenzyl-2-t-butyl-2-cyanoacetamide. Yield is 52.9
%Met.

Example 3 3.6 p,α,α-dimethylbenzylamine (3.2 g) of ethyl 2-t-amyl-2-cyanoacetate was placed in a 50WL eggplant type flask, and the mixture was heated and stirred on a 200° C. oil bath for 4 hours. After the reaction product was returned to room temperature, it was recrystallized from benzene-hexane to obtain colorless needle crystals 3.26.9. As a result of measuring the IR of this material, the absorption based on the S bond at 3310m-', the absorption based on the CH bond at 2970I:m-', and the absorption based on the CH bond at 2970I:m-'.
Absorption based on cyano bond (C=N) at 230 cm-',
1650 cra-' K7 Mid 18 go (C=0)K
showed strong absorption based on Its elemental analysis value is C74.9
Section 3, H8, 85%, N10.27, composition formula C
,,H24N20 (272,39) C calculated value for Ic 74.96%, H8,88%,
N is in good agreement with 10.28%. In addition, when MS was measured, there was a peak corresponding to yP-CM at V-257, a peak corresponding to 202-csH16, m/e1
19, H3'l(-NMR (δ: ppm: tetramethylsilane standard.

The results of measuring the deuterated chloroform (solvent) were as follows.

(b) (d) Show the triplet line of 3 protons at 0.88 ppm a
) corresponded to the methyl proton. A single line corresponding to 6 protons was shown at 1.10 ppm, which corresponded to the methyl proton in b). A quadruple line corresponding to two protons was shown at 1.51 ppm, which corresponded to the methylene proton in e). 1.72
A single line corresponding to 6 protons is shown in ppm and corresponds to the methyl proton in d). A single line corresponding to one proton is shown at 3.09 ppm, which corresponds to the methine proton of ).

A broad single line corresponding to one proton was shown at 6 and 20 ppm, which corresponded to the amino proton of f). 7.24pp
A single line corresponding to 5 protons is shown in m, which corresponds to the proton of the benzene ring in g). The above results show that the isolated product is N
-α,α-dimethylbenzyl-2-t-amyl-2-cyanoacetamide was clearly identified. The yield was 60.9%.

Example-4 Various compounds represented by the following general formulas were prepared by the same method as in Example-1 and Example-2 (However, R1e R2t R5* R4+ Xl s
(X2 and X3 are shown in Table 1) were made of synthetic leather. The yield and elemental analysis values of the synthesized compound are shown in Table 1. Also the first
The abbreviations in the table are as follows.

iPr: isoglobil group.

t-Bu: Tert-buter base formulation example 1 (granules) 2 parts by weight of the 9 compounds synthesized in Example 1, 1 part of dioctyl succinate! parts by weight, 3 parts by weight of sodium lignin sulfonate,
30 parts by weight of bentonite and 64 parts by weight of Merck were thoroughly mixed and pulverized, water was added and kneaded, and the mixture was granulated and dried.
The granules were sized to ~32 mesh to obtain 2 granules.

Formulation Example 2 (Irrigation agent) 10 parts by weight of the compound synthesized in Example 1, / +7 year old xyethylene nonylphenyl ether double Jim, 1 part by weight of alkylaryl-liglycol ether, 4 parts by weight of fine powder clay
01ii parts and 47 parts by weight of zicrite were pulverized and mixed in a hammer mill to obtain a LO water use agent.

Formulation Example 3 (Emulsion) 20X parts of the compound synthesized in Example 2, 70 parts by weight of xylene, 5 parts by weight of polyoxyethylene alkyl allyl ether N, and 5 parts by weight of alkyl sulfonate were mixed and dissolved to make a 20% emulsion. A lot of things.

Example 5 ]/A sand layer pot of 8,850 are was filled with paddy soil (alluvial loam) that had been stirred with water, and paddy weeds and 5 rice seeds (variety: Akinishiki) were sown.
The area was flooded with water. The weeds were then grown in a greenhouse at an average temperature of 25°C, and after 10 days, a predetermined drop of a diluted water solution of each chemical compound was applied to the weeds when they germinated. Three weeks later, the herbicidal effects of each test compound were investigated, and the results are shown in Table 2. However, the wide-leaved leaves shown in the table refer to azaena, azalea, red pepper, etc. The evaluation was on a 6-level scale, and the evaluation of herbicidal efficacy was expressed as a number from 0 to 5 as shown below.

0... Mushroom suppression rate 0-9% 1...
・1 10-29%2...I
30-49%3...#
50-69 Section 4.../l 7
0-89 Section 5...Weed suppression rate 90-100
Regarding chemical damage to transplanted rice, the ratio of plant height, tiller number, and total type (air dry amount) to the untreated plot was calculated, and the worst value of the three factors was taken and evaluated on a scale of 0 to 5.

0...Ratio to untreated area 100%1...
... 1 90-99 regret 2...
... 1 80-89 Section 3...
・・ 1 60~79chi 4------・
-# 40-59%5...
I Q ~ 39. Furthermore, the above general formula (
As the known compounds represented by Z), the following two types of compounds were evaluated in the same manner as above, and the results are also listed in Table 2 as comparative examples.

C) (, CH.

H3

[Brief explanation of the drawing]

1 and 2 show the infrared absorption spectrum and 1H-nuclear magnetic resonance spectrum of the compound obtained in Example 1, respectively.

Claims (1)

[Claims] (1) General formulas ▲ Numerical formulas, chemical formulas, tables, etc. are the same or different hydrogen atoms, alkyl groups, halogen atoms, halogenoalkyl groups, alkoxy groups, alkylthio groups, alkoxyalkyl groups, nitro groups or cyano groups.
-Cyanoacetamide compounds.