JPS62277306A - Improved herbicidal granular composition for paddy field - Google Patents

Abstract

PURPOSE:The titled effective composition, obtained by blending calcium carbonate and any of sodium pyrophosphate, potassium pyrophosphate or sodium tripolyphosphate with a sulfonylurea derivative and a controlling agent against weeds of the genus Echinochloa of the family Gramineae. CONSTITUTION:A herbicidal granular composition for paddy field obtained by blending (A) a sulfonylurea derivative, i.e. a herbicidally active compound having pyrimidinyl or triazinylcarbamoylsulfamoyl group, e.g. a compound expressed by formula I, etc., with (B) a compound, having <=100ppm water solubility at 20 deg.C (sparingly soluble in water) and capable of exhibiting remarkable effect on weeds of the genus Echinochloa of the family Gramineae, e.g. a compound expressed by formula II, etc., with calcium carbonate and one or two or more of sodium tripolyphosphate, sodium pyrophosphate or potassium pyrophosphate. Thereby the compound (A) is stabilized and the compound (B) is preferentially released. Since elution property of the compound (A) to water on the paddy field surface is delayed, phytotoxicity to rice plants is reduced.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention is directed to compounds having a pyrimidinyl group or a triazinyl group (hereinafter referred to as sulfonylurea) useful for controlling perennial weeds that are difficult to control in agriculture. The present invention relates to an improved herbicidal granule composition for use in rice fields, which contains a compound (referred to as a derivative) and a compound that is highly effective against weeds of the family Braceae.

(Prior Art) Many sulfonylurea derivatives are already known as herbicides (U.S. Pat. Nos. 4,127,405 and 41,697).
No. 19, JP-A No. 57-11237.9, 59-317
No. 75), it is extremely effective against perennial weeds that are controlled by li. In addition, it is known that by mixing this sulfonylurea derivative with a compound that is highly effective against weeds of the barnyard family, it becomes a labor-saving herbicide with a wide herbicidal spectrum (Japanese Patent Application Laid-Open No. 58-2010). -188803,
No. 59-82306), such a characteristic composite granule consisting of two types of compounds is a preparation that is particularly convenient for spraying as a paddy field herbicide, and it is desired to complete it.

(Problems to be Solved by the Invention) However, when this is formulated using conventional technology, the stability of the sulfonylurea derivative is insufficient when the product is stored for a long period of time, and there is a problem that it decomposes over time. be.

Techniques for stabilizing herbicidal ingredients in herbicide granules include adding various stabilizers (for example, Japanese Patent Publication No. 45
-28398, 45-28399, 46-3071
7, No. 47-24129, No. 47-37008) and a method of physically isolating herbicidal components from substances that promote decomposition (Japanese Patent Publication No. 52-21059).

In the composite granules of the present invention, a sufficient stabilizing effect cannot be obtained by adding these stabilizers, and depending on the type of stabilizer, adding them may reduce side effects such as environmental pollution after dispersing one granule. There is a concern that the following problems may occur. Furthermore, the method of coating the active ingredient with a waxy substance suppresses the release of the active ingredient into water, reducing the herbicidal effect.

On the other hand, when this composite granule formulated using conventionally known technology is applied to rice fields, the herbicidal effect of the sulfonylurea derivative is sufficiently expressed, but the herbicidal effect of the compound, which is poorly soluble in water and is highly effective against barnyard grass weeds, is effective against barnyard grass. The problem is that it decreases. This is because when sulfonylurea derivatives are treated in stamped water, they are rapidly dissolved in water, absorbed by the roots and foliage of sensitive plants such as year-old broad-leaved weeds and Cyperaceae, and undergo cell division at extremely low concentrations. inhibits.

Causes susceptible plants to die in a short period of time. However, because weeds of the family Arunaceae are less sensitive, they do not die, and growth is halted until the sulfonylurea derivatives absorbed into the bodies of the weeds of the family Arunidae are metabolized into inert substances. For this reason, the ability of weeds to absorb chemicals effective against weeds decreases until their metabolic function recovers, and during this period, water leakage and water fall occur after chemicals effective against weeds are applied to paddy fields. This is thought to be due to the fact that the amount is no longer sufficient to show a stable effect because it is lost from the rice field water through outflow, adsorption to the soil, transpiration from the rice field water, and uptake by other plants.

Therefore, it can be used as a granule for fully exhibiting the herbicidal effect of a compound that is 1i soluble in water and exhibiting an excellent effect on weeds of the family Soraceae, and for stably obtaining the herbicidal effect of a sulfonylurea derivative.

It is necessary to preferentially release compounds that are highly effective against weeds of the family Aeraceae into rice field water, and release sulfonylurea derivatives after a certain period of time (preferably 2 to 5 days).

Another known method is to obtain a stabilized aqueous composition of a compound using a water-soluble inorganic salt or the like (Japanese Unexamined Patent Publication No. 59-205305). According to this, sulfonylurea yI2+! The E form becomes a water-soluble salt in an aqueous composition and is stabilized. However, due to increased water solubility, it can be rapidly released from the granules.

As a result, the drug damage caused by this compound becomes even stronger.

A sufficient herbicidal effect cannot be obtained even if the sulfonylurea derivative is gradually released into water in small amounts, so in the present composite preparation, it is desirable to release the sulfonylurea derivative into the rice field water immediately after a certain period of time.

Conventionally, various auxiliary agents have been used as techniques related to this.

Method for promoting disintegration of grains and accelerating dissolution of components (Special Publications No. 40-25520, No. 48-38858, No. 52-47)
016, No. 53-46888), conversely, a method of suppressing the disintegration of a single grain as a technique for suppressing the elution of components (Special Publication No. 45-2200), and a method of suppressing the release of components by coating with resin (Special Publication No. 45-2200). No. 41-19080) and the like are known.

All of these technologies aim to promote the rapid release of ingredients in granules immediately after dispersion, or to gradually release small amounts of ingredients over a long period of time. The aim is either to promote or to suppress.

In contrast, in the present composite granules, it is necessary to perfect a technology that promotes the release of one component, suppresses the release of the other sulfonylurea derivative for a certain period of time, and then releases it rapidly. It was not possible to obtain a controlled compound herbicide.

The present inventors stabilized a sulfonylurea derivative that easily decomposes in granules, and after spraying, rapidly released into river water a compound in the granules that is water-soluble and highly effective against weeds of the barnyard family. Research has been carried out on ure7 derivatives with the aim of completing a formulation that releases rapidly after a certain period of time, preferably 2 to 5 days.

As a result, calcium carbonate and sodium pyrophosphate.

By blending one or more of potassium pyrophosphate or sodium tripolyphosphate into the granules, the sulfonylurea derivatives are stabilized, and after being sprayed, the sulfonylurea derivatives are soluble in water from the granules and are highly effective against weeds of the family Haeaceae. was preferentially released, and the sulfonylurea derivative was rapidly released after a certain period of time, and the present invention was completed. Furthermore, the composition of the present invention has the secondary effect of reducing phytotoxicity to paddy rice because the dissolution of the sulfonylurea derivative into rice field water is delayed.

(Means for Solving the Problems) The herbicidal granule composition of the present invention exhibits excellent efficacy against (A) sulfonylurea derivatives, (B) weeds of the family Thrushaceae, and has a water solubility of 20'.
A compound containing C of 1100 pp or less, (C) calcium carbonate, and (D) one or more of sodium tripolyphosphate, sodium pyrophosphate, or potassium pyrophosphate (hereinafter referred to as the condensed phosphate of the present invention). It becomes.

Examples of the sulfonylurea derivatives include the following compounds.

This is shown in general formula (1) below; however, the present invention is not limited to this, and can be widely applied to other compounds having pyrimidinyl or triazinylcarbamoylsulfamoyl groups.

General formula (1) %formula% Y represents CH or N, R1 represents CH or OCH3, R2 represents C1, CH, or OCH.

R1 is C1, Br, No, lower alkyl, lower alkoxy, Co2R'', So, R'.

vinegar.

On the other hand, examples of compounds that are highly effective against weeds of the family Bedweed include, but are not necessarily limited to, the following. All of these compounds have low solubility and are heated to 2°C
1100 pp or less, and is m-soluble in water.

The method for producing the granules of the present invention includes adding and mixing the active ingredient, calcium carbonate, the condensed phosphate of the present invention, and other additives such as fillers and surfactants as necessary, and adding hydrated A method of extrusion molding by mixing the ingredients, adding calcium carbonate, the condensed phosphate of the present invention, and other additives such as fillers and surfactants as necessary, adding water, and extrusion molding. After that, other ingredients are adsorbed by spraying, and after spraying and coating the active ingredients on river sand, etc., fine powder of calcium carbonate, the condensed phosphate of the present invention, and other adjuvants are added as necessary. An example of this method is to make it adhere to the surface of river sand or the like, but it is not necessarily limited to this method.

The blending ratio of calcium carbonate and the condensed phosphate of the present invention used in the present invention is not particularly limited, but desirably 10 to 90% calcium carbonate based on the weight of the composition.
Weight% 1 The condensed phosphate of the present invention is 1 to 10% by weight.

The granules of the present invention include alkylbenzene sulfonates, ligninsulfonates, which are commonly used granule auxiliaries,
Alkyl sulfosuccinate, naphthalene sulfonate,
Polyoxyethylene alkylaryl ether sulfate.

Surfactants such as polyoxyethylene alkylaryl ether, polyoxyethylene alkyl ether, polyoxyethylene fatty acid alkyl ester, alkylamine salts, fillers such as bentonite, clay, talc, diatomaceous earth, synthetic hydrated silicic acid, river sand, starch, CMC, thickeners such as polyvinyl alcohol, xylene, kerosene, methylnaphthalene, methylene chloride, isopropyl alcohol, ethylene glycol, ethyl cellosolve, cyclohexanone, dimethylformamide, acetonitrile.

Solvents such as liquid paraffin, stabilizers such as inorganic and organic acids,
In addition, inorganic salts and the like can be used as necessary.

(Function) The present invention stabilizes the sulfonylurea derivative in the granules,
Although the mechanism for controlling the elution of active ingredients from granules sprayed on rice fields is not clear, the following is thought to be the mechanism.

(2) Sulfonylurea derivatives are more stable in alkaline than acidic conditions; (1) By adding the condensed phosphate of the present invention, metals and the like contained in the filler become inactive, further improving the stability of the active ingredient.

■ Sulfonylurea derivatives are alkaline and form a kind of salt with calcium and sodium ions, etc., but calcium salts have lower solubility in water than sodium salts. 1 Because of the calcium carbonate used in the present invention, sulfonylurea derivatives have a certain water solubility. However, after the granules disintegrate and disperse in water, the solubility of the sulfonylurea derivative increases again under the influence of corrosive organic matter and clay minerals in the soil.

■ By blending the condensed phosphorus m-salt of the present invention into granules, the disintegration and dispersion of the granules in water is significantly improved, and as a result, compounds that are sparingly soluble in water and highly effective against weeds of the family Arunidae can be added to water. The dissolution rate is further improved.

(2) The condensed phosphate salt of the present invention has the effect of improving the rate of absorption of a compound that is poorly soluble in water and is highly effective against weeds of the family Thread family.

Margin below Next, an example will be given and explained.

(Examples) Example 1 0.5 parts of compound (3), 10 parts of powdered calcium carbonate, and 10 parts of sodium tripolyphosphate are mixed and ground in a hammer mill to form a fine powder.

Quartz sand (silica sand) sized to 14-32 mesh 72.5
After confirming that the surface of the quartz sand (silica sand) was evenly wetted, 20.5 parts of the fine powder was mixed with 7 parts of the compound (B).
The herbicidal granules of the present invention were obtained by adding 1 part little by little and mixing to make it adhere uniformly to the surface of quartz sand (silica sand).

Example 2 Compound (6) 0.07 parts, powdered calcium carbonate 18 parts.

Mix 1 part of potassium pyrophosphate and 2.93 parts of talc,
Grind with a hammer mill to make a fine powder.

Granular calcium carbonate sized to 14-32 mesh 72
After confirming that the surface of the granular calcium carbonate was uniformly wetted, the fine powder 21 was mixed with 7 parts of compound (A).
The herbicidal granules of the present invention were obtained by adding the above ingredients little by little and mixing to make them adhere uniformly to the surface of granular calcium carbonate.

Example 3 Compound (5') 0.75 parts, powdered calcium carbonate 30 parts, sodium tripolyphosphate 5 parts, bentonite 30 parts.

After mixing 22.25 parts of talc, 2 parts of sodium alkylbenzenesulfonate, and 3 parts of polyvinyl alcohol, the mixture is ground in a hammer mill to form a fine powder.

Appropriate water is added to this, kneaded, extruded through a screen with a diameter of 1 m, dried at 80°C, and sieved through a 14-32 mesh to obtain granules.

7 parts of compound (A) was sprayed and adsorbed onto 93 parts of the granules to obtain herbicidal granules of the present invention.

Example 4 0.25 parts of compound part (2), 4 parts of compound (D), 60 parts of powdered calcium carbonate, 3 parts of sodium pyrophosphate, 27.75 parts of bentonite, 2 parts of sodium alkylbenzenesulfonate, 3 parts of sodium ligninsulfonate After mixing parts.

Grind with a hammer mill to make a fine powder.

Appropriate amount of water was added to the mixture and kneaded, extruded through a screen with a diameter of 1 m, dried at 80°C, and sieved through a 14 to 32 mesh to obtain herb granules of the present invention.

Implementation MS 0.15 parts of compound (7), 10 parts of compound (C), 50 parts of powdered calcium carbonate, 8 parts of potassium pyrophosphate, 21.85 parts of bentonite, 5 parts of white carbon, 2 parts of sodium alkylbenzenesulfonate, lignin sulfone After mixing 3 parts of sodium chloride, the mixture is ground in a hammer mill to form a fine powder.

Appropriate water was added to the mixture, kneaded, extruded through a screen with a diameter of 1++a, dried at 80°C, and sieved through a 14-32 mesh sieve to obtain the herbicidal granules of the present invention.

Example 6 0.35 parts of compound (8), 1.3 parts of compound (E), 60 parts of powdered calcium carbonate, 3 parts of sodium tripolyphosphate, 3 parts of potassium pyrophosphate, 27.35 parts of bentonite, 2 parts of sodium alkylbenzenesulfonate 1 part and 3 parts of sodium ligninsulfonate are mixed, and then ground in a hammer mill to form a fine powder.

Appropriate water was added to this, kneaded, extruded through a screen with a diameter of 1++ m, dried at 80°C, and sieved through a 14-32 mesh sieve to obtain the herbicidal granules of the present invention.

The following margin Comparative Example 1 Compound (3) 0.5 part 2 Sodium tripolyphosphate 1
0 parts of talc and 10 parts of talc were mixed together and ground into a fine powder using a hammer mill.

Quartz sand (silica sand) sized to 14-32 mesh 72.5
After confirming that the surface of the quartz sand (silica sand) was evenly wetted, 20.5 parts of the fine powder was mixed with 7 parts of the compound (B).
A herbicide a was obtained by adding 1 part little by little and mixing to make it adhere uniformly to the surface of quartz sand (silica sand).

Comparative example 2 Compound (6) 0.07 parts, powdered calcium carbonate 18 parts.

2.93 parts of talc are mixed and ground into a fine powder using a hammer mill.

Granular carbonate 72 sized to 14-32 mesh size
After mixing 1 part and 7 parts of compound (A) and confirming that the surface of 9 granular calcium carbonate was uniformly wet, @2 fine powder 21
The herbicidal granules were obtained by adding the mixture little by little and mixing to uniformly adhere to the surface of the granular calcium carbonate.

Comparative Example 3 Compound (5) 0.75 parts, powdered calcium carbonate 30 parts,
30 parts of bentonite, 27.25 parts of talc, 2 parts of sodium alkylbenzenesulfonate, polyvinylalcohol:-
After mixing 3 parts of the mixture, pulverize with a hammer mill to make a fine powder.

The mixture is kneaded with an appropriate amount of water, extruded through a screen with a diameter of III, dried at 80 DEG C., and sieved through a 14 to 32 mesh screen to obtain granules.

7 parts of compound (A) was sprayed and adsorbed onto 93 parts of the granules to obtain herbicidal granules.

Comparative Example 4 0.25 parts of compound (2), 4 parts of compound (D), 5 parts of sodium pyrophosphate, 27.75 parts of bentonite, 60 parts of clay, 2 parts of sodium alkylbenzene sulfonate, 3 parts of sodium lignin sulfonate After mixing, crush with a hammer mill to make a fine powder.

Appropriate water was added to the mixture, the mixture was kneaded, extruded through a screen with a diameter of IIIfl, dried at 80°C, and sieved through a 14-32 mesh sieve to obtain herbicidal granules.

Comparative Example 5 0.5 parts of compound (3), 2 parts of white carbon, and 18.5 parts of clay are mixed and ground into fine powder using a hammer mill.

Mix 72 parts of quartz sand (silica sand) sized to 14-32 mesh and 7 parts of compound (B), and after confirming that the surface of the quartz sand (silica sand) is wet, add 21 parts of fine powder little by little. The herbicide granules were obtained by uniformly adhering them to the surface of quartz sand (silica sand).

Comparative Example 6 Compound (6) 0.07 parts, Compound (Δ) 7 parts, N, N-
The solution was dissolved in 2.93 parts of dimethylformamide and sprayed and adsorbed onto 90 parts of attapulgite, which was sized to 14 to 32 meshes in a one-rotation mixer. After the spraying of the solution was completed, the mixture was mixed for a while to obtain herbicide granules.

Comparative Example 7 After mixing 75 parts of compound (5) O', 5 parts of white carbon, 17 parts of bentonite, 70.25 parts of calcium carbonate, 2 parts of sodium alkylbenzene sulfonate, and 3 parts of polyvinyl alcohol, the mixture was pulverized with a hammer mill. Make into a fine powder.

Appropriate water was added to this, kneaded, extruded through a screen with a diameter of 1+ m, dried at 80°C, and sieved through a 14 to 32 mesh to obtain granules.

7 parts of compound (A) was sprayed and adsorbed onto 93 parts of the granules to obtain herbicidal granules.

Comparative Example 8 Compound (8) 0.35 parts, Compound (E) 1.3 parts, potassium pyrophosphate 3 parts, bentonite 28 parts, clay 62
．． After mixing 35 parts of sodium ligninsulfonate and 2 parts of sodium alkylbenzenesulfonate, the mixture was ground in a hammer mill to form a fine powder.

Appropriate water was added to the mixture, kneaded, extruded through a screen with a diameter of 1 m, dried at 80°C, and sieved through a 14-32 mesh sieve to obtain herbicidal granules.

Comparative Example 9 Compound (C) 10 parts, bentonite 4o parts, clay 35
1 part, 2 parts of sodium alkylbenzene sulfonate, and 3 parts of polyvinyl alcohol are mixed and ground in a hammer mill to form a fine powder.

This fine powder is kneaded with an appropriate amount of water, extruded through a screen with a diameter of 1 m, dried at 60'C, and sieved through a 16-32 mesh to obtain granules.

90 parts of this granulate are heated to 90°C. Separately, the compound (
7) 0.15 parts paraffin wax (145'''F)
The mixture was mixed with 9 parts of sorbitan monostearate and 80.85 parts of sorbitan monostearate, ground in a mortar, mixed uniformly with the heated granules, cooled, and sieved through a 14-mesh sieve to obtain herbicidal granules.

Comparative Example 1 1.11 parts of sodium ligninsulfonate and 4.48 parts of sodium hydroxide were dissolved in 54.35 parts of water, and while stirring, 21.3 parts of compound (2) was added little by little and reacted to form a water-soluble solution. produced the sodium salt. Add 4.68 parts of sodium acetate to this solution and after 5 minutes add 4.68 parts of sodium acetate.
Added 8 parts. After approximately 15 minutes, it was confirmed that the sodium salt of compound (2) would rapidly precipitate, and then an additional 9.35 parts of sodium acetate was added. The resulting composition was ground in a sand mill 7 to produce particles with a particle size of 5 microns or less.

Polysaccharide thickener was added several minutes to complete the milling operation.

Sodium salt of this compound (2) @4 liquid (component content 2
1.1%) 1.2 parts, Compound (D) 4 parts, sodium ligninsulfonate 3 parts, sodium alkylbenzenesulfonate 2 parts, bentonite 40 parts, clay 50.75
1 part, mix and crush with a hammer mill to make a fine powder.

Appropriate water was added to the mixture, kneaded, extruded through a screen with a diameter of 1 m, dried at 60'C, and sieved through a 14-32 mesh sieve to obtain herbicidal granules.

The effects of the present invention are shown below.

Margins below (Effects of the invention) The herbicidal granules of the present invention have good stability of herbicidal ingredients, and at the same time fully exhibit the properties of the herbicidal ingredients, so there is no chemical harm to paddy rice and a wide herbicidal spectrum against weeds. It is an excellent composite herbicide granule that exhibits

Test Example 1 Herbicide granules were sealed in a glass bottle and stored in a constant temperature machine at 50°C for a predetermined period of time. After the abuse treatment, the sulfonylurea derivative content in each herbicidal granule was determined by high performance liquid chromatography, and the content of other compounds was determined by high performance liquid chromatography or gas chromatography.

The decomposition rate was determined from the change in compound content before and after the abuse treatment.

The results are shown in Table 2.

Margin below (Table 2) Test Example 2 (Water dissolution test of active ingredients) 3 degree hard water 80 in a 1/5000a Wagner Point in a constant temperature room at 20℃
I took 0m1+ and took a still image. Approximately 80 square meters of accurately weighed herbicide granules (corresponding to spraying 4 kg of granules per 10 a) were sprayed therein.

1, 3, and 5 days after spraying, pour 5 liters of water from the center of each pot.
Collect with a 0mQ whole pipette. After extraction with chloroform, it was concentrated using a rotary evaporator, and the content of the sulfonylurea derivative was determined by high performance liquid chromatography, and the content of other compounds was determined by high performance liquid chromatography or gas chromatography, and the concentration in water was calculated from that value, and the content was eluted in water. The dissolution rate in water was determined from the amount (μg) of each compound and the amount (μg) of each compound contained in the dispersed granules using the following formula.

The results are shown in Table 3.

Blank space below (Table 3) Test Example 3 (Medical efficacy/toxicity test) <Medical efficacy test> In a greenhouse, fill a 1/5000a Wagner bonoto with paddy soil, add water, fertilize, and rak for the first generation. did. In addition, in another pot, six sprouted tubers of Cyperus japonica were buried in water so that the buds would emerge.

The water was flooded to a depth of 3 am.

The chemical treatment was applied to one Japanese millet per pot when the leaf age of Japanese millet was 2 leaves, and when the leaf age was about 2 leaves (grass and bamboo 10-15).
Align 5 plants and 3 plants of Mizugaya spp. with the prescribed amount of each # herb granule.
Weigh out i (equivalent to spraying 1.5 kg of granules per loa),
Each spray was applied in triplicate.

The investigation was conducted by measuring the aboveground dry weight 30 days after the chemical treatment and comparing it with the untreated plot.

Plant damage test〉 Fill paddy soil in a 1/5000 a. Three plants were transplanted to two countries at a transplant depth.

It was flooded to a depth of 3.

For chemical treatment, two days after transplanting, a predetermined amount of each herbicide granule (equivalent to spraying 6 kg of granule per 108) was weighed out and sprayed in triplicate. The leaf age at the time of treatment was 2.2 to 2.3 leaves.

The above-ground dry weight was measured 30 days after the drug treatment.

Comparison was made with the untreated area.

In the untreated area, weeds were completely removed by hand to avoid weed damage.

The results of the drug efficacy/toxicity tests are shown in Table 4 below.

Margin below

Claims (2)

[Claims] (1) (A) a herbicidally active compound having a pyrimidinyl or triazinylcarbamoylsulfamoyl group, (B)
Contains one or more of the following compounds: (C) calcium carbonate, and (D) sodium tripolyphosphate, sodium pyrophosphate, or potassium pyrophosphate, a compound that has a water solubility of 100 ppm or less at 20°C and is highly effective against weeds of the family Fiberaceae. An improved herbicide granule composition for paddy fields characterized by: (2) The herbicidally active compound having a pyrimidinyl or triazinylcarbamoylsulfamoyl group has the following general formula [
The herbicidal granule composition for paddy fields according to claim 1, which is represented by [I]]. General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, X is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, There are ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables etc. ▼, Y indicates CH or N, R^1 indicates CH_3 or OCH_3, R^2 indicates C
l, CH_3 or OCH_3, R^3 is Cl,
Br, NO_2, lower alkyl group, lower alkoxy group,
CO_2R^6, SO_2R^6 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and R^4, R^5, R^6 and R^7 represent H or a lower alkyl group.