JPS5918361B2 - Phytotoxicity reducer of N-substituted or unsubstituted phenylcarbamoyl amino acid derivatives - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention uses a bifurcated type (
n) [In the formula, X and Y are the same or different and represent a hydrogen atom,
It represents a halogen atom, a nitro group, a methylsulfonyl group, a trifluoromethyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms.

R2 is a hydrogen atom, a carboxymethyl group, or a carbon number of 1 to
3 shows the alkyl group.

R3 relates to a novel composition for alleviating drug-induced adverse effects, which are undesirable side effects of -CH2-1 or unsubstituted phenylcarbamoyl amino acid derivatives, salts thereof, or esters thereof.

Many of the compounds of general formula (II) or their salts or esters are disclosed in West German Patent No. 1023628, West German Patent Publication No. 1902457, West German Patent Publication No. 2005326, or US Patent No. 3020.
It is described in the specification of No. 145.

Among these documents, West German Patent Publication No. 2005326 describes, for example, N-(3,4-dichlorophenyl)-N contained in the compound of general formula (II).
'-Methyl-N'-(2-carboxyethyl) urea is harmless to wheat, barley, and oats, and has a herbicidal effect on weeds such as field grass, sycamore, Japanese radish, chickweed, wild currant, etc. It is stated that.

Further, West German Patent Publication No. 1902457 describes, for example, 1-('3'-)I contained in the compound of general formula (n).
It has been stated that when J-fluoromethylphenyl)-3-methyl-3-carboxymethylureas are applied during the cultivation of corn, rice, tomatoes, etc., weeds such as sycamore, staghorn mole, sycamore, chickweed, and field weed are killed. There is.

However, it has also been shown that some phytotoxicity is observed in corn, rice, and tomatoes.

West German Patent No. 1023628 describes, for example, β-methyl-δ-(3.4
There is a statement that -dichlorophenyl) hydantoic acids eliminate weeds that are harmful to agriculture.

However, there is no mention that the herbicidal effect is selective, and there is a statement that it kills oats.

For example, US Pat. No. 3,020,145 describes the general formula (
It has been described that N-(parachlorophenylcarbamoyl)-N-methyl-β-alanine contained in the compound (n) causes the death of not only broad-leaved weeds but also weeds of the Phytaceae family.

Furthermore, the present inventors have synthesized a large number of compounds of general formula (n) or their esters or salts thereof, and have
When applied to oats, beer barley, rye, corn, etc., it was found that the tolerance of these crops to the above compounds was generally not very good.

This poor tolerability is due to the fact that, for example, in wheat, when a compound of bifurcated formula (II), its ester, or its salt is sprayed as a herbicide when the tree has one to two leaves, it is applied to the third leaf. It is recognized by delayed or suppressed growth of new leaves, yellowing of these new leaves, and lodging of the stems.

Therefore, the present inventors conducted a wide search for a compound that has the effect of reducing the above-mentioned phytotoxicity without weakening the herbicidal effect of the compound of general formula (n) or its salt or ester, and found that it did not exhibit herbicidal activity itself. , rather, the general formula (I) H2N-R1-NH2(I) which sometimes shows a slight growth promoting effect [wherein R1 is a -(CH2)n- group (in the formula, n represents an integer of 4 to 18) -( CH2)3NH(CH2)4 group,
(CH2)4 NH(CH2)4 two groups, -(CH2)
Polyamine compounds represented by 3NH(CH2)4NI ((CH2)3 group, fluorenylene group or naphthylene group) and their acid salts do not weaken the herbicidal action of the compound of general formula (II) (reduce phytotoxicity). The present invention was completed based on this knowledge.

That is, the present invention relates to a drug harm reducer of a compound of general formula (n), a salt thereof, or an ester thereof, which is characterized by containing a compound of general formula (D) or an acid salt thereof.

On the other hand, examples of herbicides that have the effect of reducing phytotoxicity of crops include Nibutam, a corn herbicide.
N-N-diallyl-2,2-dichloroacetamide (Weed 5ci
enceλ1 (4) 1292″295 (1973)) and 1,8-naphthalene fanhydride (Weed 5cience 22 (1
), 86-90 (1974)) are known, but
Both herbicides and drug reducers have different structures from those according to the present invention.

Next, the present invention will be explained in detail.

In the definition of the compound of general formula (I[), in the definition of X and Y, the halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Regarding the definition of , refers to an n-propoxy group or an i-propoxy group.

Regarding the definition of R2, the alkyl group having 1 to 3 carbon atoms refers to a methyl group, ethyl group, n-propyl group or i-propyl group.

Examples of the salts of the compound of general formula (n) include salts with alkali metals such as sodium and potassium, ammonium salts, and salts with primary amines such as methylamine, ethylamine, and propylamine.

The ester of the compound of general formula (II) has 1 to 1 carbon atoms.
4 alkanols, such as methanol, ethanol,
Examples include esters with -gropanol, n-butanol, etc.

In the definition of the compound of general formula (I), the -(CH2)n- group is a tetramethylene group, hexamethylene group, octamethylene group, nonamethylene group, decamethylene group, dodecamethylene group, tetradecamethylene group, hexadecamethylene group. group, octadecamethylene group, etc.

Examples of the fluorenylene group include a 2,7-fluorenylene group, and examples of the naphthylene group include a 1,8-naphthylene group.

The acid salts of the compound of general formula (I) include hydrochloride, sulfate,
Examples include inorganic or organic acid salts such as carbonates, phosphates, formates, acetates, and propionates.

Representative examples of the polyamine represented by the general formula (I) are as follows.

Tetramethylene diamine, pentamethylene diamine, hexamethylene diamine, ■・8-diaminooctane, ■
・9-diaminononane, ■・10-diaminodecane, 1
・12-diaminododecane, 1,14-diaminotetradecane, 1,16-diamithexadecane, ■・18-
Diaminoctadecane, ■・8-diaminonaphthalene,
■2-diaminonaphthalene, 2,7-diaminofluorene, spermidine, homospermidine, spermine, etc.

The compound of general formula (II), its salt, or its ester has its chemical toxicity reduced by the polyamine of general formula (I), and there are suitable combinations of both compounds.

That is, the compound of general formula (n) or its salt or its ester is N-methyl-N-(3,4--)chlorophenylcarbamoyl)chrysin.1 aqueous phase product, N-methyl-N=(3,4--) dichlorophenylcarbamoyl)-
In the case of salts or esters of β-alanine, polyethylene diamines having 8 to 12 carbon atoms from 1,8-diaminooctane to 1,12-diaminododecane, diaminofluorene, diamino naphthalene, etc. have a strong drug-toxicity reducing effect. show.

Among them, 1,8-diaminooctane and 1,9-diaminononane exhibit the strongest effects.

In addition, when the compound of general formula (II) or its salt or its ester is N-methyl-N-(3,4-dichlorophenylcarbamoyl)-γ-aminobutyric acid or its salt or its ester, 1,12-diamino Polymethylene diamines having 12 to 18 carbon atoms, ranging from dodecane to 1,18-diaminooctadecane, exhibit strong phytotoxicity reducing effects.

Among them, polymethylene diamines having 16 to 18 carbon atoms, such as 1,16-diamithexadecane and 1,18-diaminooctadecane, exhibit the strongest effects.

Although not directly related to the present invention, some amine compounds that are relatively similar to the polyamine of the present invention also have the effect of slightly reducing the phytotoxicity of the compound of general formula (n) or its salt or ester. There are some compounds, which are exemplified below, but these compounds are inferior to the compound of general formula (I) or its acid salt in terms of reducing drug damage.

3,4-diaminotoluene, 2,4-diaminotoluene, 1,2-diaminocyclohexane, 1,4-diaminoanthraquinone, 1,5-diaminoanthraquinone, D
L-ornithine, L-lysine, DL-arginine, L-
Citrulline, L-glutamine, 1-aminopropane, ■
-aminobutane, ■-aminopentane, 1-aminehebutane, 1-amineoctane, ■-aminononane, ■-aminodecane, ■-aminoundecane, ■-aminododecane, cyclohexylamine, ■-aminoanthraquinone, 〇-toluidine, m -) Luidine, DL-norvaline, L-norleucine, chrysine, L-cysteine, glutathione, L-glutamic acid, L-aspartic acid, etc.

Note that the present inventors have determined that the general formula (n
Among other compounds known to have herbicidal activity other than the compound 4-
Amben (3-amino-2,5-dichlorobenzoic acid), Endothal (7-ofsabicyclo[2.
2.1] hebutane-2,3-dicarboxylic acid), Benazolin (4-chloro-2-octabenzothiazolin-3-yl-acetic acid, MCPA (4-
chloro-2-methylphenoxyacetic acid), 2,4-PA (
2,4-dichlorophenoxyacetic acid), MDBA (3,6
-dichloro-〇-anisic acid) etc., the general formula (I)
It is expected that polyamines or amine-based compounds similar to these will exhibit drug-toxicity reducing effects.

Next, N- containing the polyamine represented by the general formula (I) or its acid salt of the present invention, represented by the general formula (n)
As the safener for substituted or unsubstituted phenylcarbamoyl amino acid derivatives, salts thereof, or esters thereof, the compound of general formula (I) or its acid salt itself;
Alternatively, the compound of general formula (I) or its acid salt may be mixed with a commonly used pesticide adjuvant, and if necessary, a fertilizer or other pesticide.

These safeners are used as water-solvent type, wettable powder type, powder coating type, emulsion type, granule type, etc.

Pesticide auxiliaries include solvents, carriers, surfactants, and fixing agents.

The solvent must be inert not only to the compound of general formula (I) or its acid salt, but also to the compound of general formula (n), its salt, or its ester, but generally water, n -Hexane, cyclohexane, benzene, chlorobenzene, ethylene glycol, ethyl ether, acetone, ethyl acetate, dimethylformamide and the like.

Supports include bentonite, talc, diatomaceous earth, synthetic alumina, phenolic resin, and white carbon (product name:
Shionogi & Co., Ltd.).

Examples of the surfactant include sodium lauryl sulfate, stearyltrimethylammonium chloride, and polyoxyethylene alkylphenyl ether.

Examples of the fixing agent include casein, carboxymethyl cellulose, and glue.

Other agricultural chemicals include insecticides, fungicides, acaricides, nematicides, other herbicides, antiviral agents, plant growth regulators, attractants, and the like.

The mode of use of the above-mentioned drug harm reducer of the present invention is as follows.

(1) A method of using the phytotoxicity reducing agent of the present invention by coating the seeds of crops of the Physcomitraceae family (2) Dipping seeds of crops of the Physcomitraceae family in a diluted solution of the phytotoxicity reducing agent of the present invention with water, etc. Method of use (3) General formula (n
) A method of applying the herbicide of the present invention to soil or to crops of the family Herbaceae before or after using a herbicide containing an N-substituted or unsubstituted phenylcarbamoyl amino acid derivative, a salt thereof, or an ester thereof (
4) Method of applying a mixture of a herbicide containing the compound of general formula (n) or its salt or ester and the safener of the present invention The amount of the safener of the present invention to be used in these usage modes is subject to the following. It should be changed depending on the crop, application time, application location, weed growth conditions, etc., and cannot be discussed in general.

However, in the case of (1) above, the phytotoxicity reducer is usually 0.01 to 10%, preferably 0.1%, as the active ingredient, the compound of general formula (I) or its acid salt, per seed of crops belonging to the Herbaceae family.
~5% (w/w.

(hereinafter referred to as W/W). In the case of (2), the general formula (
The concentration of the compound I) or its acid salt is 0.01 to 1
0%, preferably 0.01-1% (weight/volume).

(hereinafter referred to as W/V), the seeds of a plant belonging to the Phytaceae family are immersed in a diluted solution for about 1 to 72 hours.

In the case of 3) above, 50 to 1000 f of the compound of general formula (I) or its acid salt is applied per 10 are.

In the case of (4) above, N- represented by the general formula (I[)
A herbicide containing a substituted or unsubstituted phenylcarbamoyl amino acid derivative, a salt thereof, or an ester thereof and a phytotoxicity reducing agent of the present invention containing a polyamine compound represented by the general formula (I) or an acid salt thereof, are combined into a compound of the general formula (
The molar ratio of the compound of n) or its salt or its ester and the compound of general formula (I) or its acid salt is 1 mole of the former to 0.2 mole or more of the latter, particularly considering the degree of drug damage reducing effect and economic efficiency. Taking into consideration, for every 1 mole of the former, 1 to 1 mole of the latter
It is appropriate to mix so that the amount is 4 mol.

60 to 4000 g of the compound of general formula (n) or its salt or its ester per 10 are of the blend mixed in such a ratio, preferably 150 to 75 g.
0? Apply to control weeds.

In addition, in the case of application mode 4) above, the water suspension properties of both the herbicide and the phytotoxicity reducer are improved.

In other words, a good dispersion and suspension state can be maintained for a longer period of time than when each component is dissolved in water alone.

Next, the content of the present invention will be specifically explained with reference to Examples.

Example 1 5 parts by weight of water-solvent type octamethylene diamine were uniformly mixed and dissolved in 95 parts by weight of water to obtain a water-solvent containing 5% by weight of the active ingredient.

Example 2 Wettable powder type octamethylene diamine 30 parts by weight Trade name of sodium alkylbenzenesulfonate: Toho Kagaku Talc 30 parts by weight Bentonite 35 parts by weight were uniformly mixed and finely ground to form a wettable powder containing 30% by weight of the active ingredient. I got it.

Example 3 Wettable powder type ■・12-diaminododecane 30 parts by weight Lunotsu Soup-65-L 5 parts by weight Talc
30 parts by weight bentonite
35 parts by weight were uniformly mixed and finely ground to obtain an aqueous phase agent containing 30% by weight of the active ingredient.

Example 4 Seed dressing type Octamethylene diamine 50 parts by weight Triton A seed dressing was prepared by adding 2 parts by weight of this seed dressing to 98 parts by weight of wheat seeds to coat the surface of the seeds to obtain coated seeds containing 1% of the active ingredient.

Example 5 Emulsion type 10-diaminodecane 50 parts by weight dimethylformamide 30 parts by weight xylene
155 parts by weight Nirasannonion N
520 5 parts by weight of polyoxyethylene alkyl phenyl ether (trade name: Ninirasan oil) and above were mixed to obtain an emulsion containing 50% (W/W) of active ingredients.

Example 6 Granule type ■・9-diaminononane 3 parts by weight White carbon 3 parts by weight Sodium ligninsulfonate 2 parts by weight Bentonite
92 parts by weight were uniformly mixed and pulverized, mixed with a small amount of water, granulated using an extrusion granulator, and dried to obtain granules.

Example 7 Aqueous phase agent type octamethylene diamine 19.5 parts by weight Bentonite 52.0 parts by weight were uniformly mixed and ground to prepare a wettable powder.

Example 8 Emulsion type (1) 11.7 parts by weight of 10-diaminodecane 7.6 parts by weight of Nirasannonion N5206 60.0 parts by weight of isophorone were mixed and stirred to obtain an emulsion.

Example 9 Granule type 9-diaminononane 4.3 parts by weight Bentonite 79.0 parts by weight White carbon 5.0 parts by weight were uniformly mixed and pulverized, mixed with a small amount of water, and granulated using an extrusion granulator. After processing and drying, granules were obtained.

Example 10 Water-solvent typed 18-diaminooctadecane 5 parts by weight water
95 parts by weight were uniformly mixed to obtain an aqueous solvent containing 5% by weight of the active ingredient.

Example 11 Wettable powder type 18-diaminooctadecane 30 parts by weight Lunotsu p-65-L5 parts by weight Talc 30 parts by weight Bentonite 35 parts by weight were uniformly mixed and finely ground to form a wettable powder containing 30% by weight of the active ingredient. Obtained.

Hereinafter, it will be specifically shown by giving test examples that the drug damage reducing agent of the present invention has a remarkable effect of reducing drug damage.

Test Example 1 Test on the effect of reducing phytotoxicity by soaking seeds A phytotoxicity reducer (water-solvent type) prepared in the same manner as in Example 1 and N-methyl-N-(3,4-dichlorophenylcarbamoyl)glycine monohydrate 50 A herbicide (wettable powder type) obtained by uniformly mixing and pulverizing 3 parts by weight of sodium dodecylbenzenesulfonate and 47 parts by weight of bentonite was diluted with water, and both solutions were prepared as shown in Table 1. Prepare the mixture in a petri dish, add 10 grains of rice (variety: Zennanfu) and 1 grain of wheat (variety: Norin No. 27).
0 radish (variety: spring-sown early radish) 10 radish, Amaranthus retroflexus
20 seeds (L, ) were each sown and allowed to germinate and grow in a room maintained at 25°C.

Four days after sowing, the length of the above-ground part was measured and the average length was calculated, and Table 1 shows the average length ratio of each test plot when the average length (dragon) of the untreated plot was set as 100. .

For rice seeds only, paddy that had been subjected to water absorption treatment for 2 days before sowing was used. Prepare a large number of things in perforated pots, and put wheat (variety: Norin No. 27) and wild foxtail grass (varietal: Norin No. 27) in separate pots.
5etaria viridis P, Beauv,
), Amaranthus retref
Lexus L, ) and daikon radish (variety: spring-sown early radish) seeds are sown uniformly in fixed quantities and covered with soil, and then grown under outdoor conditions where there is no influence of rainfall. , Japanese radish and Japanese radish are allowed to reach 1.8 to 2 true leaves, 2 leaves, 0.5 to 1 true leaf, and 3rd leaf extraction stage, respectively.

The numbers of wheat, foxtail grass, green grass, and radish are adjusted to 30, 25, 100, and 5, respectively.

N-methyl-N-(3.
A herbicide (wettable powder type) containing Chrysin (4-dichlorophenylcarbamoyl) 1 aqueous phase, prepared in the same manner as in Example 2, or using Chrysin 2 in place of octamethylene diamine.
N-methyl- The weight ratio of N-(3,4-dichlorophenylcarbamoyl)glycine monohydrate and polyamine or amine compound is 4 for the former and 6 for the latter.
Mix it so that
Ru N-(,3,4-dichlorophenylcarbamoyl)
The concentration of glycine monohydrate is 0.4% (W/V
) and polyamine at a concentration of 0.6% (w/v), resulting in a herbicide/toxicity reducer mixed solution.

Meanwhile, the herbicide was dissolved in water and N-methyl-N-(3.
A herbicide solution with a concentration of 4-dichlorophenylcarbamoyl) chrysin monohydrate of 0.4% (w/v) was prepared, and the above-mentioned phytotoxicity reducer was dissolved in water to prepare a polyamine or an amine compound other than the polyamine of the present invention. 1 as the concentration of
% (w/v) of the drug harm reducer liquid.

The thus prepared herbicide/harm reducer mixture, herbicide solution, or harm reducer solution was applied to wheat that showed the above-mentioned growth.
The stems and leaves of green foxtail, green grass, and dogroot were sprayed using a micro-spraying device until they were almost uniformly wet.

Measure the fresh weight (2) of the above-ground parts of each plant on the 14th day after the drug treatment, and when the fresh weight of the untreated area/3 is taken as 100, calculate the fresh weight ratio of each test area and see Table 2 and It is shown in Table 3.

*N-#-ruN-(3,4-dichlorophenylcarbamoyl)chrysin monohydrate 0.4% (w/v), polyamine or other amine compound 0.6% (w/v) *Polyamine or other amine compound 1.0% (W
/V) Test Example 3 Non-simultaneous treatment of phytotoxicity reducer and herbicide Wheat, foxtail grass, and green grass were grown in the same manner as the test plant growing method specified in Test Example 2,
2-2.3 true leaves, 1.2-1.5 true leaves and 0 true leaves, respectively.
．． Allow to reach 1-0.5 leaves.

The number of wheat, foxtail grass, and green grass is 3 each.
Adjust to 0 lines, 30 lines, and 150 lines.

A herbicide ( hydrating agent type)
in water, N-methyl-N-(3,4-dichlorophenylcarbamoyl)glycine monohydrate 0.2% (w
/v) A herbicide liquid is applied to wheat, foxtail grass, and green grass during the growing season using a micro-spraying device until the leaves and stems are almost uniformly wetted.

Then, immediately after the plant stems and leaves treated with the herbicide solution have dried, or after the number of days shown in Table 4, a phytotoxicity reducer (wettable powder type) prepared in the same manner as in Example 2 is added to water, and octamethylene is added. A phytotoxicity reducing agent solution containing 0.2% (w/v) diamine was prepared, and this was sprayed on the leaves of the plants in the same manner as the herbicide solution treatment.

14 days after herbicide solution treatment Above ground fresh weight of each plant
were measured, and the degree of recovery of plants from chemical damage and herbicidal effects were investigated.

Taking the average fresh weight of the untreated plot as 100, the fresh weight ratio of each treated plot was determined and shown in Table 4.

Test Example 4 Simultaneous treatment of phytotoxicity reducer and herbicide Wheat (variety: Norin No. 27), foxtail grass, and blueberry were grown in the same manner as the test plant growing method specified in Test Example 2, and each had 2 to 2 true leaves. .2 leaves (10-15C
IrL), 2 lobes (2-3.5cIrL) and 0.5-
Achieve one lobe (1-1.5 CIrL).

Wheat) 1-no.: The number of 1-o. grains and Aobiyu are adjusted to 30, 25, and 150, respectively.

On the other hand, in the same manner as in Example 2, a drug harm reducer (wettable powder type) containing octamethylenediamine as an active ingredient was added to N-methyl-N-(3,4-dichlorophenylcarbamoyl)chrysin in the same manner as in Test Example 1.・Herbicides containing monohydrate as the active ingredient (wettable powder type) and N-methyl-N
N -methyl-N
Herbicides (wettable powder type) each containing -(3,4-dichlorophenylcarbamoyl)-β-alanine methyl ester as an active ingredient are prepared.

Either dilute each wettable powder with water or further mix the herbicide liquid and the herbicide reducer liquid after dilution to create a herbicide/harm reducer mixture having the active ingredient concentration shown in Tables 5 and 6. Prepare liquid, herbicide liquid and safener liquid.

Each chemical solution prepared as described above was sprayed using a micro-atomizer until the leaves and stems of the test plants were almost uniformly wetted.

After foliage treatment, the fresh weight of the aboveground parts of each plant was measured on day 14.
was measured, and when the fresh weight of the drug-free plot was taken as 100, the fresh weight ratio of each drug-treated plot was determined and shown in Tables 5 and 6.

This test was conducted in a greenhouse.

Test Example 5 Effect of reducing phytotoxicity on various crops In the same manner as the test plant growing method specified in Test Example 2,
Beer barley (Hordeum clistichum L)
.

emend Lam, ), oats (Avena 5
ativa L, ), rye (5ecale ce
reale L, ), barley (Hordeum unl)
gare L, ), rice (0ryza 5ativ
aL, ) and maize (Zeamays L,
) in separate pots, each with 2 true leaves.
~2.2 leaves (plant height 13-17 cfrL), 1.5-1.
8 leaves (plant height 7-9 degrees), 2 leaves (plant height 9-12 crn),
1.5-2 leaves (plant height 6-8CrrL), 2.1-2.3
Leaves (plant height 9-12 crIL) and 3-leaf (plant height 12-1 crIL)
6CrfL).

The numbers of beer wheat, oats, rye, barley, rice and corn are adjusted to 25, 30, 15, 20 and 8, respectively.

In the same manner as in Test Example 1, N-methyl-N-(3・☆・4-
A herbicide (wettable powder type) containing dichlorophenylcarbamoyl)glycine monohydrate and a phytotoxicity reducer (wettable powder type) containing 1,8-diaminooctane are prepared in the same manner as in Example 2.

Either dilute each hydrate with water, or further mix the herbicide liquid and the herbicide liquid after dilution, and then
A herbicide/harm reducer mixture, a herbicide solution, and a harm reducer liquid having the active ingredient concentrations shown in the table are prepared.

Each chemical solution prepared as described above was sprayed using a micro-spraying device until the leaves and stems of the test plants were almost uniformly wetted.

Fresh weight of above-ground parts of each crop on the 16th day after foliage treatment
was measured, and when the fresh weight of the drug-free plot was taken as 100, the fresh weight ratio of each drug-treated plot was determined and shown in Tables 7 to 12.

(b) In Tables 7 to 12, b=1.36X10
"Test Example 6 Effect of reducing phytotoxicity on various crops" In the same manner as the test plant growing method specified in Test Example 2,
Beer barley (Hordeum clistichum L)
.

emend Lam, ), oats (Avena 5
ativa L, ), rye (5 ecale cer
eale L,) 1 Barley (Hordeum uulga)
re L, ), rice (0ryza 5ativa L,), and corn (zeamays L, ) were grown in separate pots, with 1.5-2 true leaves (plant height 10-13CrfL) and 1.3-1.6 true leaves, respectively. Leaves (plant height 7-10 crrL), 2 leaves (plant height 10-14 crrL)
, 1.2-1.5 leaves (plant height 7-10 cIrL), 3 leaves (
Achieve a plant height of 13-15 CrrL) and 2.3-2.6 leaves (Plant height 12-16 cfrL).

The numbers of beer wheat, oats, rye, barley, rice, and corn are 30, 20, 30, and 20, respectively.
Adjust to 20 lines and 8 lines.

Test Example 1 ON-Methyl-N-(3,4-dichlorophenylcarbamoyl)chrysine monohydrate ★50 parts by weight of N-methyl-N-(3,4-dichlorophenylcarbamoyl)-β-alanine methyl ester N-methyl-N- was prepared in the same manner as Test Example 1 except that parts by weight were used.
Herbicide containing (3,4-dichlorophenylcarbamoyl)-β-alanine methyl ester (wettable powder type)
Then, in the same manner as in Example 1, a drug harm reducer (water-solvent type) containing 1,8-diaminooctane is prepared.

From these wettable powders, aqueous solvents, and water as a diluent, herbicide/harm reducer mixtures and herbicide solutions having the active ingredient concentrations shown in Table 13 are prepared.

Each chemical solution prepared as described above is sprayed using a micro-spraying device until the leaves and stems of the test plant are almost uniformly wetted.

Fresh weight of the aboveground parts of each crop on the 16th day after foliage treatment
was measured, and when the fresh weight of the chemical-free area was taken as 100, the fresh weight ratio of each chemical-treated area was determined and shown in Table 13.

@) C=1.36
Norin No. 27), yellow mustard greens, and green beetles were grown in separate pots, with 3 to 3.5 true leaves (plant height 19 to 24 cIrL) and 1.5 to 2 leaves (plant height 2.5 to 2.5 cIrL), respectively.
3 crrL) and 3.5-4 leaves (plant height 2-3.5Cr
fL).

The number of wheat, yellow currant, and blueberry is 20 each.
adjust to books, 30 books, and 100 books.

N-methyl-N-(3,4-dichlorophenylcarbamoyl)glycine monohydrate, N-
Methyl-N-(3,4-dichlorophenylcarbamoyl)glycine methyl ester, N-methyl-N-(3,4
-dichlorophenylcarbamoyl)-β-alanine, N
-Methyl-N-(3,4-dichlorophenylcarbamoyl)-β-alanine methyl ester, N-methyl-N-
Herbicides (wettable powder type) containing (3,4-dichlorophenylcarbamoyl)-γ-aminobutyric acid and N-methyl-N-(3,4-dichlorophenylcarbamoyl)-γ-aminobutyric acid methyl ester, respectively, and implementation A drug harm reducer (water-solvent type) containing 1,8-diaminooctane is prepared in the same manner as in Example 1.

From these aqueous phase agents, aqueous solvents, and water as a diluent, herbicide/harm reducer mixtures and herbicide solutions having active ingredient concentrations shown in Tables 14 to 31 are prepared.

Each chemical solution prepared as described above is sprayed using a micro-spraying device until the leaves and stems of the test plant are almost uniformly wetted.

Fresh weight of above-ground parts of each crop on the 16th day after foliage treatment
When the fresh weight of the chemical-free area is taken as 100, the fresh weight ratio of each chemical-treated area is calculated and shown in Tables 14 to 31.
Shown in the table.

(b) In Tables 14 to 31, d ~1.36. X
10-2 Test Example 8 In the same manner as the test plant growing method specified in Test Example 2,
Wheat (variety: Norin No. 61), edible vinaigrette and Aobiyu were grown in separate pots, and 2.5% of each tree's leaves were grown.
2-2.5 leaves (plant height 15-17 crrL), 2-2.2
Leaves (plant height 9-10 CIIL) and 1-1.2 leaves (plant height 15-17 CrrL) are reached.

The numbers of wheat, edible vinyl, and blueberry are adjusted to 15, 25, and 180 to 220, respectively.

Test Example 1 50 parts by weight of N-methyl-N-(3,4-dichlorophenylcarbamoyl)-γ-aminobutyric acid instead of 50 parts by weight of ON-methyl-N-(3,4-dichlorophenylcarbamoyl)chrysin monohydrate A herbicide (wettable powder type) containing N-(3,4-dichlorophenylcarbamoyl)-γ-aminobutyric acid was prepared in the same manner as in Test Example 1, except that the same procedure was used as in Test Example 1.

A drug harm reducer (water-solvent type) containing 1,8-diaminooctane is prepared in the same manner as in Example 1.

Further, in place of 5 parts by weight of 1,8-diaminooctane in Example 1, ■9-diaminonane, ■10-diaminodecane, ■12-diaminododecane, ■14-diaminotetradecane, and ■16-diaminodecane were added. A phytotoxicity reducer (water-solvent type) containing each of these diamines is prepared in the same manner as in Example 1, except that 5 parts by weight of each of hexadecane and 1,18-diaminooctadecane are used.

From these wettable powders, aqueous solvents, and water as a diluent, herbicide/harm reducer mixtures and herbicide solutions having active ingredient concentrations shown in Tables 32 to 52 are prepared.

Spray each of the prepared chemical solutions as described above using a micro-spraying device until the leaves and stems of the test plant are almost uniformly wet.

Fresh weight of above-ground parts of each crop (1)
was measured, and when the fresh weight of the drug-free plot was taken as 100, the fresh weight ratio of each drug-treated plot was determined and shown in Tables 32 to 52.

(b) In Tables 32 to 52, e=1.36X10
``By using the chemical damage reducer of the present invention, it is possible to control weeding while maintaining the normal and healthy growth of crops belonging to the Phytophthora family over the entire growing season from the early stage of germination to the tillering stage to the heading stage. Therefore, it has become possible to apply a herbicide containing an N-substituted rubamoyl amino acid derivative represented by general formula (I), a salt thereof, or an ester thereof.

Claims (1)

[Claims] 1 General formula (I) [In the formula, R1 is a -(CH2)n- group (In the formula, n is 4 to 1
8), -(CH2)3NH(CH2), one group, -(CH2), N)((CH2)4 one group, (CH2)
2) 3Nu(CH2)4NH(CH2)3 group, fluorenylene group or naphthylene group] or an acid salt thereof;
General formula (n) [In the formula, X and Y are the same or different, a hydrogen atom,
It represents a halogen atom, a nitro group, a methylsulfonyl group, a trifluoromethyl group, an alkyl group having 1 to 3 carbon atoms, or an alkoxy group having 1 to 3 carbon atoms. R2 is a hydrogen atom, a carboxymethyl group, or a carbon number of 1 to
3 shows the alkyl group. A drug harm reducer containing an N-substituted or unsubstituted phenylcarbamoyl amino acid derivative, a salt thereof, or an ester thereof. 2. The drug harm reducer according to claim 1, which is in a mixed state with the compound of general formula (I[) or its salt or its ester.