JP6739128B1 - Granulating property improving agent for agrochemical composition and agrochemical composition using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a granulating property improving agent for an agrochemical composition and an agrochemical composition using the same. SOLUTION: The granulating property improving agent for agrochemical compositions of the present invention contains a compound represented by the following general formula (1). HO-R1-O-A1-H (1) [In the formula (1), R1 is an alkylene group having 6 to 14 carbon atoms, and A1 is a divalent group represented by -(R5O)S-. And R5 is an alkylene group having 2 or 3 carbon atoms, s is an integer of 1 to 10, and when s is 2 or more, all R5 in -(R5O)S- are the same. , May be different. ] [Selection diagram] None

Description

TECHNICAL FIELD The present invention relates to a granulating agent for pesticide composition and a pesticide composition using the same. More specifically, the present invention is, for example, used as a raw material for an agrochemical composition, and at the time of producing a granular agrochemical by an extrusion molding machine, it is possible to reduce the load applied to the molding machine. The present invention relates to an improving agent and an agrochemical composition using the same.

Conventionally, agricultural chemicals used in agriculture are composed of a composition containing an agricultural chemical active ingredient (hereinafter, also referred to as "agrochemical active ingredient") and other ingredients. Then, in order to control the dissolution of the pesticide active ingredient, and also for ease of weighing or spraying by a person engaged in agriculture, and when the pesticide active ingredient is a powder, it can be directly sucked at the time of spraying. From the viewpoint of being suppressed, pesticides granulated into granules are widely used. A product obtained by granulating such an agricultural chemical composition is, for example, after uniformly mixing and kneading the agricultural chemical active ingredient with a solid carrier, a binder, a surfactant, water, etc., and then extruding the kneaded product. Manufactured.

Regarding granulation of a pesticide composition, Patent Document 1 discloses a carrier having a predetermined specific surface area, a surfactant made of an organic phosphate ester represented by a predetermined chemical formula, a predetermined pesticide active ingredient and water. Disclosed is a method for producing a pesticide granule by extruding a water-containing composition contained at a mass ratio of

Japanese Patent Laid-Open No. 11-79902

The above-mentioned Patent Document 1 discloses that in the granulation of an agricultural chemical composition, an agricultural chemical granule is produced by extrusion molding. Here, when granulating the pesticide composition, due to the load applied to the molding machine such as an extruder, when the pesticide composition can not be sufficiently granulated, or in the production of granules of the pesticide composition Workability may decrease.

The present invention has been made in view of the state of the art as described above, and can be used as a raw material for agricultural chemicals, and the load applied to the molding machine in the granulation step of the agricultural chemical composition containing the agricultural chemical raw material is reduced. Another object of the present invention is to provide a granulating property improving agent for agricultural chemicals, which can suitably obtain a granulated product. Another object of the present invention is to provide an agrochemical composition containing a granulating agent for agrochemicals, which can reduce the load applied to a molding machine during granulation and can be preferably granulated.

As a result of diligent research, the present inventors have found that when a specific diol compound is used as an agricultural chemical raw material in an agricultural chemical composition, the load on the molding machine in the granulation step of the agricultural chemical composition is reduced, and the agricultural chemical composition is reduced. It has been found that it exhibits excellent effects on the granulation of and the workability of granulating the agrochemical composition is excellent.

The present invention is as follows.
1. A granulating property improving agent for agrochemical compositions, which comprises a compound represented by the following general formula (1).
^{HO-R 1 -O-A 1} -H (1)
[In the formula (1), R ¹ is an alkylene group having 6 to 14 carbon atoms, A ¹ is a divalent group represented by —(R ⁵ O) _S —, and R ⁵ is a carbon atom. The number is an alkylene group of 2 or 3, s is an integer of 1 to 10, and when s is 2 or more, all R ⁵ s in -(R ⁵ O) _S — are the same or different. Good. ]
2. Furthermore, the above 1. containing a compound represented by the following general formula (2). The granulating property improving agent for agricultural chemical compositions as described in 1.
^{H-A 2 -O-R 2} -O-A 3 -H (2)
[In the formula (2), R ² is an alkylene group having 6 to 14 carbon atoms, A ² is a divalent group represented by —(OR ⁷ ) _t —, and R ⁷ is 2 or 3 carbon atoms. an alkylene group, - ^(OR _{7) t} - also in ^{R 7} may be the same or different, t is an integer from 1 to 10, ^{a 3} is - ^(R 9 _{O) u} - in a divalent group represented, R ⁹ is an alkylene group having 2 or 3 carbon ^{atoms, - (R 9 O) u} - even R ⁹ are all the same in the or different, u is an integer of 1-10. ]
3. The content of the compound represented by the general formula (1) and the compound represented by the general formula (2) is represented by the general formula (1) when the total amount thereof is 100% by mass. 2. The compound is 50 to 99% by mass, and the compound represented by the general formula (2) is 1 to 50% by mass. The granulating property improving agent for pesticide composition according to.
4. Above 1. To 3. A pesticidal composition comprising the pesticidal composition granulating agent according to any one of 1.
5. Furthermore, the above-mentioned 4. containing an agricultural chemical raw material and a bulking agent. The agrochemical composition according to.
6. The contents of the granulating property improving agent for pesticide composition, the pesticide raw material, and the bulking agent are respectively 0.1 to 10 mass% and 0.01 to 100 mass% when their total is 100 mass %. 90% by mass and 0.5 to 99.8% by mass, which is 5. The agrochemical composition according to.

Granulation improver for agrochemical compositions of the present invention, in the production of agrochemical compositions containing agrochemical raw materials, at the time of granulation when using this as a granulated product, load applied to a molding machine such as an extrusion molding machine Can be sufficiently reduced, excellent workability can be exhibited in granulation of the agrochemical composition, and a granulated product of the agrochemical composition can be efficiently produced.
Further, since the agrochemical composition of the present invention contains the granulation property improving agent for the agrochemical composition, at the time of granulation in the case of a granulated product, the load applied to the molding machine such as an extrusion molding machine is sufficiently reduced. It is possible to efficiently produce a granulated product of an agricultural chemical composition.

The granulating property improving agent for agricultural chemical compositions of the present invention contains a compound represented by the following general formula (1) (hereinafter referred to as "diol compound 1").
^{HO-R 1 -O-A 1} -H (1)
[In the formula (1), R ¹ is an alkylene group having 6 to 14 carbon atoms, A ¹ is a divalent group represented by —(R ⁵ O) _S —, and R ⁵ is a carbon atom. The number is an alkylene group of 2 or 3, s is an integer of 1 to 10, and when s is 2 or more, all R ⁵ s in -(R ⁵ O) _S — are the same or different. Good. ]

In the general formula (1), the structure of the alkylene group R ¹ is not particularly limited and may be linear or branched. The alkylene group for R ¹ has 6 to 14, preferably 8 to 12 carbon atoms. The alkylene group R ¹ is preferably a branched alkylene group having 8 to 12 carbon atoms because the load applied to the extruder and the like is further reduced. Specific examples of preferable R ¹ are shown below.

In the general formula (1), the alkylene group R ⁵ that constitutes A ¹ is an alkylene group having 2 or 3 carbon atoms, that is, an ethylene group or a linear or branched propylene group. Thus, ^{A 1} comprises an oxyethylene group _{(-C 2} H 4 O-) or an oxypropylene group _{(-C 3} H 6 O-).
In the diol compound 1, s, which is the total number of oxyethylene groups or oxypropylene groups, is 1 to 10, preferably 2 to 6, and more preferably 3 to 5. If s is 2 or ^{more, - (R 5 O) S} - also all R ⁵ are the same in, may be different, if it contains both oxyethylene groups and oxypropylene groups, these groups It has a structure in which it is connected regularly or irregularly.

The method for producing the diol compound 1 is not particularly limited. A preferred production method comprises a step of reacting an alkanediol having 6 to 14 carbon atoms with at least one selected from ethylene oxide and propylene oxide in the presence of a catalyst (hereinafter referred to as "reaction step"). Method (hereinafter, referred to as “first manufacturing method”). The first manufacturing method will be described below.

Examples of the alkanediol include straight-chain alkanediols such as hexanediol, heptanediol, octanediol, nonanediol, decanediol, undecanediol, dodecanediol, tridecanediol, and tetradecanediol; 2-butyl-2-ethyl-1, Examples thereof include branched alkanediols such as 3-propanediol, 2,4-diethyl-1,5-pentanediol, and 2-methyl-1,8-octanediol. The alkanediol used in the reaction step may be only one kind, or may be two or more kinds.

A catalyst is used in the reaction step. The catalyst is not particularly limited, but it is preferably a basic compound because the desired product can be efficiently obtained. The basic compound may be either an inorganic compound or an organic compound, and examples of the inorganic compound include potassium hydroxide, sodium hydroxide, lithium hydroxide, potassium carbonate, sodium carbonate and lithium carbonate. Examples of the organic compound include CH ₃ ONa, C ₂ H ₅ ONa, CH ₃ OLi, C ₂ H ₅ OLi, CH ₃ OK, C ₂ H ₅ OK and the like. The amount of the catalyst used is preferably 0.1 to 10 mmolequivalent based on 1 mol of the alkanediol.

The reaction step is carried out in a pressure reactor such as an autoclave while the temperature of the reaction system is preferably 100°C to 170°C, more preferably 130°C to 150°C while stirring the raw materials. Ethylene oxide or propylene oxide can be added while changing the order, the ratio, etc. in order to obtain a diol compound having a desired structure.

In the said 1st manufacturing method, a purification process can be provided after a reaction process as needed. This purification step can include conventionally known operations such as chromatographic separation and concentration, which are performed in general synthesis of organic compounds.

The granulating property improving agent for agricultural chemical compositions of the present invention contains the above-mentioned diol compound 1, and further contains a compound represented by the following general formula (2) (hereinafter referred to as "diol compound 2"). it can.
^{H-A 2 -O-R 2} -O-A 3 -H (2)
[In the formula (2), R ² is an alkylene group having 6 to 14 carbon atoms, A ² is a divalent group represented by —(OR ⁷ ) _t —, and R ⁷ is 2 or 3 carbon atoms. an alkylene group, - ^(OR _{7) t} - also in ^{R 7} may be the same or different, t is an integer from 1 to 10, ^{a 3} is - ^(R 9 _{O) u} - in a divalent group represented, R ⁹ is an alkylene group having 2 or 3 carbon ^{atoms, - (R 9 O) u} - even R ⁹ are all the same in the or different, u is an integer of 1-10. ]

In the general formula (2), the structure of the alkylene group R ² is not particularly limited and may be linear or branched. The alkylene group in R ² has 6 to 14 carbon atoms, preferably 8 to 12 carbon atoms. The alkylene group R ² is preferably a branched alkylene group having 8 to 12 carbon atoms because the load applied to the extruder and the like is further reduced. Specific examples of preferable R ² are shown below.

In addition, in the general formula (2), the alkylene group R ⁷ that constitutes A ² is an alkylene group having 2 or 3 carbon atoms, that is, an ethylene group or a linear or branched propylene group. Therefore, ^{A 2} is an oxyethylene group containing _(-OC 2 _{H 4} - -) or oxypropylene group _(-OC 3 _{H 6).}
In the diol compound 2, t, which is the total number of oxyethylene groups or oxypropylene groups, is 1 to 10, preferably 2 to 6, and more preferably 3 to 5. When t is 2 or more, all R ^{7 s} in -(OR ⁷ ) _t- may be the same or different, but when both oxyethylene groups and oxypropylene groups are contained, these groups have a regular structure. It has a structure in which it is connected in a continuous or irregular manner.

In addition, in the general formula (2), the alkylene group R ⁹ that constitutes A ³ is an alkylene group having 2 or 3 carbon atoms, that is, an ethylene group or a linear or branched propylene group. Accordingly, ^{A 3} contains an oxyethylene group _{(-C 2} H 4 O-) or an oxypropylene group _{(-C 3} H 6 O-).
In the diol compound 2, u, which is the total number of oxyethylene groups or oxypropylene groups, is 1 to 10, preferably 2 to 6, and more preferably 3 to 5. If u is 2 or more, - (R 9 ^O) u _- even R ⁹ are all the same in, may be different, if it contains both oxyethylene groups and oxypropylene groups, these groups It has a structure in which it is connected regularly or irregularly.

The method for producing the diol compound 2 is not particularly limited. A preferred production method is an alkanediol having 6 to 14 carbon atoms similar to the alkanediol used in the production of the above-mentioned diol 1, and at least one selected from ethylene oxide and propylene oxide in the presence of the above-mentioned basic catalyst. It is a manufacturing method including a step of reacting with.
As the method for producing the above-mentioned diol 2, for example, except that the amount of the basic catalyst used in the reaction is 10 to 100 mmol equivalents (preferably 15 to 50 mmol equivalents) per 1 mol of the alkanediol, The production method of the diol compound 1 can be the same.

Since the granulating property improving agent for agrochemical compositions of the present invention contains the above-mentioned diol compound 1, it is possible to reduce the load applied to a molding machine such as an extrusion molding machine in the production of granulated products and the like.
Further, the granulating property improving agent for agricultural chemical compositions of the present invention may further contain a diol compound 2 as another component. When the granulation improver for pesticide composition of the present invention also contains the diol compound 2, the load applied to the molding machine may be slightly increased as compared with the diol compound 1 alone, but the mass ratio is not a practical problem. Then, the diol compound 2 can be added.

When the granulating property improving agent for agricultural chemicals composition of this invention contains the diol compound 1 and the diol compound 2, the content of the diol compound 1 and the diol compound 2 is 100 mass% of the total of the diol compound 1 and the diol compound 2. In each case, the content is preferably 50 to 99% by mass and 1 to 50% by mass, and more preferably 70 to 95% by mass and 5 to 30% by mass.

Further, the pesticidal composition granulating property improver of the present invention further contains other components such as a binder, a spreader, a disintegrant, a dispersant, an emulsifier, and a solvent, within a range in which the effect of the present invention is not suppressed. can do.

The pesticidal composition of the present invention contains the above-mentioned granulating agent for pesticidal composition of the present invention, and may further contain other components. Other ingredients include agrochemical bulks and bulking agents.
The content of the granulating property improving agent for pesticide composition, pesticide raw material and extender in the pesticide composition is preferably 0.1 to 10% by mass and 0, respectively, when the total of these is 100% by mass. 0.01 to 90% by mass and 0.5 to 99.8% by mass.

The pesticide active ingredient used in the pesticide composition is not particularly limited as long as the activity is not impaired by coexistence with water, and various herbicides, insecticides, fungicides, plant growth regulators may be used. it can.

Herbicides include 6-methyl-3[1-methyl-1-(3,5-dichlorophenyl)ethyl]-5-phenyl-2,3-dihydro-4H-1,3-oxazin-4-one. , (RS)-2-(2,4-Dichloro-m-tolyloxy)propionanilide (Chromeprop), methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (biphenox), 3-(4, 6-dimethoxypyrimidin-2-yl)-1-[(2-methoxycarbonylbenzyl)sulfonyl]urea (bensulfuronmethyl) and the like can be mentioned.

As the insecticide, 2-(4-ethoxyphenyl)-2-methylpropyl=3-phenoxybenzyl=ether (ethofenprox), (RS)-α-cyano-3-phenoxybenzyl=(RS)-2, 2-dichloro-1-1(4-ethoxyphenyl)cyclopropanecarboxylate (cycloprotoline), N-tert-butyl-N'-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide (tebufenozide), etc. Is mentioned.

As the fungicide, 1-(4-chlorobenzyl)-1-cyclobenzyl-3-phenylurea (pencyclone), 6-(3,5-dichloro-4-methylphenyl)-3(2H)-pyridazinone (diclomedin) Etc.

As plant growth regulators, indole butyric acid, eticlozet, chlorella extract, mixed crude drug extract, hydroxyisoxazole, benzylaminopurine, oxyethylenedocosanol, maleic acid hydrazide, ethefone, choline, gibberezin, inabenfide, uniconazole, daminogit. , Paclobutrazol, flurprimidol, prohexadione calcium salt and the like.

These pesticide raw materials may be used alone or in combination of two or more. The content of each pesticide raw material can be set to a predetermined amount according to each activity, and is not particularly limited, but is preferably 0.01 to 100% with respect to the total amount (100% by mass) of the pesticide composition. It is 90% by mass, more preferably 0.1 to 80% by mass.

Examples of the extender used in the agrochemical composition include various known inorganic powders, low-molecular water-soluble compounds, synthetic resin powders, organic powders and the like. Examples of the inorganic powder include bentonite, talc, clay, diatomaceous earth, amorphous silicon dioxide, calcium carbonate, magnesium carbonate and the like. Examples of the low-molecular water-soluble compound include sodium sulfate, ammonium sulfate, potassium chloride, urea and the like. Examples of the synthetic resin powder include vinyl chloride powder, polyethylene powder, chlorinated polyethylene powder, chlorinated polypropylene powder and the like. Furthermore, examples of the organic powder include sugars such as glucose, fructose, sucrose, and lactose, carboxymethyl cellulose and salts thereof, starch and derivatives thereof, wood flour, rice bran, bran, chaff, cork, and the like.

These fillers may be used alone or in combination of two or more. The content of the extender is not particularly limited, but is preferably 0.5 to 99.8 mass%, more preferably 3 to 97 mass% with respect to the total amount of the pesticide composition.

The shape of the agrochemical composition of the present invention is not particularly limited, but a granular material is preferable.
As the method for producing the agrochemical composition of the present invention, granulation can be performed with a molding machine such as a screw molding machine, a roll molding machine, or a blade molding machine. In addition, the granulated product is usually dried and, if necessary, sized to give an agricultural chemical granule. Further, the type of the molding machine, the operating conditions and the like can be appropriately set depending on the properties of the granulating property improving agent for pesticide compositions, the mechanical properties required for the granulated product, and the like.

Hereinafter, the present invention will be specifically described with reference to examples.
1. Synthesis of diol compound 1 Synthesis example 1
After charging 160.3 g (1 mol) of 2-butyl-2-ethyl-1,3-propanediol in an autoclave and adding 0.3 g of potassium hydroxide powder (6 mmol equivalent to the raw material) as a catalyst, the autoclave The inside was sufficiently replaced with nitrogen gas. Next, while maintaining the reaction temperature at 130 to 150° C. under stirring, 176 g (4 mol) of ethylene oxide was press-fitted to carry out an addition polymerization reaction, and the mixture was aged at the same temperature for 1 hour to complete the addition polymerization reaction. After that, the catalyst was neutralized with phosphoric acid, and then by-products were separated by liquid chromatography, and the obtained reaction product was subjected to LC-MS analysis under the following conditions, and represented by the following formula (3). It was found to be a compound. Hereinafter, this diol compound 1 is shown as a-1 (see Table 1).
ESI-MS: m/z=337 (M+H) ⁺

The above LC-MS analysis was performed under the following conditions.
Measuring equipment: LC/Ultimate 3000 (made by Thermo Fisher Scientific)
: MS/maXis (manufactured by Bruker)
LC column: ACQUITY UPLC BEH C18 1.7um 2.1mm x 150mm (Waters)
Ionization method: ESI (Positive)
Ion source temperature: 200℃
MS detector: TOF
Measurement range: 70m/z-1550m/z
The compounds of Synthesis Examples 2 to 19 below were also subjected to LC-MS analysis in the same manner as in Synthesis Example 1.

Synthesis example 2
Compound a-2 was obtained by performing the same operation as in Synthesis Example 1 except that 4 mol of propylene oxide was used instead of 4 mol of ethylene oxide (see Table 1).

Synthesis example 3
Compound a-3 was obtained in the same manner as in Synthesis Example 1 except that a mixture of 2 mol of ethylene oxide and 2 mol of propylene oxide was used instead of 4 mol of ethylene oxide (see Table 1).

Synthesis example 4
Instead of the addition polymerization reaction in which ethylene oxide (4 mol) of Synthesis Example 1 was pressed and aged at the same temperature for 1 hour, 2 mol of ethylene oxide was pressed at 130° C. to 150° C. for 1 hour at the same temperature. After aging, 2 mol of propylene oxide was injected under pressure at 130° C. to 150° C., and aging was performed at the same temperature for 1 hour to complete the addition polymerization reaction. After the completion of the reaction, the same operation as in Synthesis Example 1 was performed to obtain compound a-4 (see Table 1).

Synthesis example 5
Instead of the addition polymerization reaction in which ethylene oxide (4 mol) of Synthesis Example 1 was pressed and aged at the same temperature for 1 hour, 2 mol of propylene oxide was pressed at 130° C. to 150° C. and the temperature was maintained at the same temperature for 1 hour. After aging, 2 mol of ethylene oxide was injected under pressure at 130° C. to 150° C. and aged at the same temperature for 1 hour to complete the addition polymerization reaction. After the completion of the reaction, the same operation as in Synthesis Example 1 was performed to obtain compound a-5 (see Table 1).

Synthesis example 6
2,4-diethyl-1,5-pentanediol was used in place of 2-butyl-2-ethyl-1,3-propanediol, and the amount of ethylene oxide used was changed from 4 mol to 3 mol. The same operation as in Synthesis Example 1 was performed to obtain compound a-6 (see Table 1).

Synthesis example 7
2,5-dimethyl-2,5-hexanediol was used in place of 2-butyl-2-ethyl-1,3-propanediol, and the amount of ethylene oxide used was changed from 4 mol to 5 mol. The same operation as in Synthesis Example 1 was performed to obtain compound a-7 (see Table 1).

Synthesis example 8
Compound a-8 was obtained in the same manner as in Synthesis Example 1 except that the amount of ethylene oxide used was changed from 4 mol to 6 mol (see Table 1).

Synthesis Example 9
Similar to Synthesis Example 1 except that 1,12-dodecanediol was used in place of 2-butyl-2-ethyl-1,3-propanediol and the amount of ethylene oxide used was changed from 4 mol to 6 mol. The operation was performed to obtain compound a-9 (see Table 1).

Synthesis example 10
Compound a-10 was obtained in the same manner as in Synthesis Example 1 except that 6 mol of propylene oxide was used instead of 4 mol of ethylene oxide (see Table 1).

Synthesis Example 11
Compound a-11 was obtained in the same manner as in Synthesis Example 1 except that the amount of ethylene oxide used was changed from 4 mol to 9 mol (see Table 1).

Synthesis Example 12
Instead of the addition polymerization reaction in which ethylene oxide (4 mol) of Synthesis Example 1 was pressed and aged at the same temperature for 1 hour, 4 mol of ethylene oxide was pressed at 130°C to 150°C, and the temperature was maintained at the same temperature for 1 hour. After aging, 5 mol of propylene oxide was injected under pressure at 130° C. to 150° C. and aged at the same temperature for 1 hour to complete the addition polymerization reaction. After the completion of the reaction, the same operation as in Synthesis Example 1 was performed to obtain compound a-12 (see Table 1).

Synthesis Example 13
Compound a-13 was obtained by performing the same operation as in Synthesis Example 1 except that 1,14-tetradecanediol was used instead of 2-butyl-2-ethyl-1,3-propanediol. reference).

Synthesis Example 14
Compound a-14 was obtained by performing the same operations as in Synthesis Example 1 except that 1,6-hexanediol was used instead of 2-butyl-2-ethyl-1,3-propanediol (Table 1). reference).
The compounds synthesized in Synthesis Examples 1 to 14 and the raw materials thereof are summarized in Table 1 above.

Synthesis Example 15
Compound ra-1 was obtained in the same manner as in Synthesis Example 1 except that the amount of ethylene oxide used was changed from 4 mol to 12 mol (see Table 2).

Synthesis Example 16
Compound ra-2 was obtained in the same manner as in Synthesis Example 1 except that the amount of ethylene oxide used was changed from 4 mol to 16 mol (see Table 2).
The compounds synthesized in Synthesis Examples 15 to 16 and the raw materials thereof are summarized in Table 2 above.

2. Synthesis of diol compound 2 Synthesis example 17
After charging 160.3 g (1 mol) of 2-butyl-2-ethyl-1,3-propanediol in an autoclave and adding 0.9 g of potassium hydroxide powder (18 mmol equivalent to the raw material) as a catalyst, the autoclave The inside was sufficiently replaced with nitrogen gas. Next, while maintaining the reaction temperature at 130 to 150° C. under stirring, 176 g (4 mol) of ethylene oxide was press-fitted to carry out an addition polymerization reaction, and the mixture was aged at the same temperature for 1 hour to complete the addition polymerization reaction. After that, the catalyst was neutralized with phosphoric acid, and then by-products were separated by liquid chromatography to obtain a diol compound 2 (compound b-1) represented by the following (4) (see Table 3).

Synthesis Example 18
Synthesis Example 17 except that 2-methyl-1,8-octanediol was used instead of 2-butyl-2-ethyl-1,3-propanediol and the amount of ethylene oxide used was changed from 4 mol to 6 mol Compound b-2 was obtained by performing the same operation as in (see Table 3).

Synthesis Example 19
Compound b-3 was obtained in the same manner as in Synthesis Example 17 except that the amount of ethylene oxide used was changed from 4 mol to 6 mol (see Table 3).

Synthesis example 20
Compound b-4 was obtained in the same manner as in Synthesis Example 17 except that the amount of ethylene oxide used was changed from 4 mol to 10 mol (see Table 3).
The compounds synthesized in Synthesis Examples 17 to 20 and the raw materials thereof are summarized in Table 3 above.

3. Preparation of Agrochemical Composition 80% by mass of K clay (manufactured by Showa KDE Co., Ltd.), 5% by mass of Kunigel V1 (manufactured by Kunimine Industries Co., Ltd.) as a bulking agent, and 2% by mass of bensulfuron-methyl as a pesticide bulk were uniformly mixed. Then, 3% by mass of diol compound 1 and/or 2% of diol compound 2 was added to this mixture, 10% by mass of water was added (total 100% by mass), and the mixture was uniformly kneaded. Then, this kneaded material (kneaded clay) was subjected to a screw type extrusion molding machine (manufactured by Fuji Paudal Co., model “DG-L1 type”) equipped with a screen having a diameter of 1.0 mm, an inverter frequency of the motor was 20 Hz, and a shaft Extrusion molding was carried out under the condition of a rotation speed of 32 rpm to prepare a granular pesticide composition.

Examples 1-20 and Comparative Examples 1-6
Above 3. When the granular pesticide composition was prepared as described above, the diol compound 1 (or compound ra-1 or ra-2) and the diol compound 2 in Examples 1 to 20 and Comparative Examples 1 to 6 were prepared according to Table 4 (Implementation). Examples 1 to 20) and the total amount of (diol compound 1 (or compound ra-1 or ra-2) and diol compound 2 used in the compounding ratios shown in Table 5 (Comparative Examples 1 to 6) were 100 mass. %).

4. Evaluation of Load during Extrusion Molding The evaluation criteria are based on the maximum extrusion load and the minimum extrusion load applied to the extruder when preparing the agrochemical compositions (agrochemical granules) of Examples 1 to 20 and Comparative Examples 1 to 6. The extrusion resistance was evaluated by determining as described below, and the results are shown in Tables 4 and 5.
Extrusion maximum load: Maximum torque voltage (V) immediately after putting the kneaded clay into the 350 seconds
<Evaluation criteria>
◎ ◎: 1.0V or more and 2.9V or less ◎: 3.0V or more and 3.9V or less ○: 4.0V or more and 4.9V or less △: 5.0V or more and 9.9V or less ×: 10.0V or more Minimum extrusion load The minimum torque voltage (V) immediately after the kneading material is put and after 350 seconds have passed
<Evaluation criteria>
◎ ◎: 0.60 V or more and 0.99 V or less ◎: 1.00 V or more and 1.29 V or less ○: 1.30 V or more and 1.49 V or less △: 1.50 V or more and 1.59 V or less ×: 1.60 V or more

According to Table 4, in Examples 1 to 7 using only the diol compound 1, both the maximum extrusion load and the minimum extrusion load are small, and the load during extrusion molding is sufficiently small. Further, in Examples 11 to 12, 15 to 16 and 19 to 20, the proportion of the diol compound 2 increases and the maximum load of extrusion increases in particular, but this is within the allowable range and there is no problem. Furthermore, in Examples 8, 9 and 10 in which only different kinds of diol compounds 1 were used, the minimum extrusion load was slightly higher, and in Examples 13, 14 and Examples 17 and 18, both the maximum extrusion load and the minimum extrusion load were slightly high. Although it increases, it is within the allowable range and there is no particular problem.

On the other hand, according to Table 5, in Comparative Examples 1 and 2 using the compounds ra-1 and ra-2 in which s in the formula (1) is 10 or more, both the maximum extrusion load and the minimum extrusion load are Δ. , It turns out to be inferior. Further, in Comparative Examples 3 to 6 using only the diol compound 2, both the maximum load of extrusion and the minimum load of extrusion were considerably large, and both the maximum load evaluation and the minimum load evaluation were x, indicating that they were inferior.

The granulating property improving agent for agrochemical compositions of the present invention, in the production of agrochemical compositions and the like containing the agrochemical raw material, sufficiently reduces the load applied to the molding machine of the extrusion molding machine when using this as a granulated product. Can be made. This makes it possible to obtain a granulated product of an agrochemical composition having a suitable shape and a well-balanced retention property. Further, since the pesticidal composition of the present invention contains the granulating property improving agent for the pesticidal composition, the load applied to the molding machine such as an extrusion molding machine when the granulated product is sufficiently reduced, and the pesticide composition It is possible to efficiently produce a granulated product. This makes it possible to obtain a granulated product of an agrochemical composition having a suitable shape and a well-balanced retention property. Therefore, the granulating property improving agent for agricultural chemical compositions of the present invention can be used in the technical field of producing various granular materials such as agricultural chemical compositions.
Further, the granulation property improving agent for pesticide compositions of the present invention is not limited to pesticide compositions, but as a granulation property improving agent for forming all granulated materials (granular material), various granular compositions It is possible to reduce the load applied to the extruder and the like when manufacturing the above. Further, regardless of the form, the load applied to the extruder or the like when molding by extrusion molding can be reduced.

Claims (6)

A granulating property improving agent for agrochemical compositions, which comprises a compound represented by the following general formula (1).
^{HO-R 1 -O-A 1} -H (1)
[In the formula (1), R ¹ is an alkylene group having 6 to 14 carbon atoms, A ¹ is a divalent group represented by —(R ⁵ O) _S —, and R ⁵ is a carbon atom. The number is an alkylene group of 2 or 3, s is an integer of 1 to 10, and when s is 2 or more, all R ⁵ s in -(R ⁵ O) _S — are the same or different. Good. ] Furthermore, the granulating property improving agent for agricultural chemical compositions of Claim 1 containing the compound represented by the following general formula (2).
^{H-A 2 -O-R 2} -O-A 3 -H (2)
[In the formula (2), R ² is an alkylene group having 6 to 14 carbon atoms, A ² is a divalent group represented by —(OR ⁷ ) _t —, and R ⁷ is 2 or 3 carbon atoms. an alkylene group, - ^(OR _{7) t} - also in ^{R 7} may be the same or different, t is an integer from 1 to 10, ^{a 3} is - ^(R 9 _{O) u} - in a divalent group represented, R ⁹ is an alkylene group having 2 or 3 carbon ^{atoms, - (R 9 O) u} - even R ⁹ are all the same in the or different, u is an integer of 1-10. ] The content of the compound represented by the general formula (1) and the compound represented by the general formula (2) is 100% by mass,
The compound represented by the general formula (1) is 50 to 99 mass%,
The granulating property improving agent for agricultural chemical compositions according to claim 2, wherein the compound represented by the general formula (2) is 1 to 50% by mass. An agrochemical composition comprising the granulation improver for an agrochemical composition according to any one of claims 1 to 3. The pesticide composition according to claim 4, further comprising a pesticide raw material and a bulking agent. The contents of the granulation improver for pesticide composition, the pesticide raw material and the bulking agent are respectively 0.1 to 10 mass% and 0.01 to 100 mass% when the total of them is 100 mass %. 90% by mass and 0.5 to 99.8% by mass, the agrochemical composition according to claim 5.