Liquid agrochemical composition

Abstract

Provided is an agrochemical composition comprising an auxin herbicide, and particularly a dicamba amine salt and another specific agrochemical active compound, wherein volatilization of the auxin herbicide can be suppressed, and decomposition of the specific agrochemical active compound can also be suppressed. Provided is a liquid agrochemical composition comprising: at least one type of herbicide selected from the group consisting of auxin herbicides and agriculturally acceptable salts or esters thereof; an agrochemical active compound having a partial structure represented by the formula -C(=O)-X- [wherein, X represents at least one type selected from the group consisting of an oxygen atom and NR1, and R1 represents a monovalent group]; and at least one component selected from the group consisting of polycarboxylic acids and salts thereof.

Description

Liquid pesticide composition

[0001] The present invention relates to a liquid pesticide composition.

[0002] U.S. Pat. No. 9,743,664 (Patent Document 1) describes that the volatilization of an auxin herbicide can be suppressed by adding a monocarboxylic acid or a salt thereof and a base such as potassium hydroxide to an agricultural chemical composition containing the auxin herbicide or a salt thereof.

[0003] U.S. Patent No. 9,743,664

[0004] When the above-mentioned conventional technology is applied to a pesticide composition containing, in addition to an auxin herbicide, another specific pesticidal active compound, the volatilization of the auxin herbicide can be suppressed, but there is a problem in that the specific pesticidal active compound decomposes.

[0005] An object of the present invention is to provide a pesticide composition containing an auxin herbicide, particularly a dicamba amine salt, and another specific pesticidal active compound, which can suppress the volatilization of the auxin herbicide and the decomposition of the specific pesticidal active compound.

[0006] The present invention provides the following liquid pesticide composition: [1] A liquid pesticide composition comprising at least one herbicide selected from the group consisting of auxin herbicides and agriculturally acceptable salts or esters thereof, and a compound represented by the following formula (I): —C(═O)—X— (I) [wherein X represents an oxygen atom and NR １ and R represents at least one selected from the group consisting of １ represents a monovalent group.] and at least one member selected from the group consisting of polycarboxylic acids and salts thereof. [2] The liquid pesticide composition according to [1], wherein the at least one herbicide comprises a dicamba amine salt. [3] The pesticide active compound is a compound represented by the following formula (I-1): [wherein X has the same meaning as above. ２ represents a monovalent group. ３ represents a monovalent group when X is an oxygen atom, and １ When C(=O)-R ４Represents R ４ represents a monovalent group, and R ２ and R ４ And, R ２ the carbon atoms bonded to X and R ４ [4] The liquid pesticide composition according to [2], wherein the polycarboxylic acid comprises at least one polycarboxylic acid selected from the group consisting of a copolymer of acrylic acid and maleic acid and polyacrylic acid. [5] The liquid pesticide composition according to any of [2] to [4], wherein the dicamba amine salt comprises at least one dicamba amine salt selected from the group consisting of dicamba diglycolamine salts and dicamba monoethanolamine salts. [6] The liquid pesticide composition according to any of [2] to [5], further comprising a basic component. [7] The liquid pesticide composition according to any of [2] to [5], further comprising an alkali metal hydroxide. [8] The liquid pesticide composition according to any of [2] to [5], further comprising at least one alkali metal hydroxide selected from the group consisting of potassium hydroxide and sodium hydroxide. [9] The liquid pesticide composition according to [6], wherein the concentration of the basic component is 0.0001 mol / L or more and 0.050 mol / L or less.

[10] The liquid pesticide composition according to any one of [2] to [9], wherein the pesticidal active compound comprises a PPO inhibitor.

[11] The pesticidal active compound is represented by the following formula (I-1a): [In the formula, R １ represents a monovalent group. ２ represents a monovalent group. ４ represents a monovalent group, and R ２ and R ４ And, R ２ The carbon atom, N atom, and R bonded to ４ The liquid pesticide composition according to any one of [2] to

[10] , wherein the compound represented by formula (I-1a) is a compound represented by the following formula (I-1aa): [In the formula, R ２ represents a monovalent group.４ represents a monovalent group, and R ２ and R ４ And, R ２ The carbon atom, N atom, and R bonded to ４ may form a ring together with the carbon atom bonded to R ｄ represents a fluorine atom or a hydrogen atom. ｅ represents a monovalent group which may contain one or more heteroatoms. ｆ represents a monovalent group which may contain one or more heteroatoms or a halogen atom, R ｆ and R ｅ may be taken together to form a ring. Z represents a C—H or N atom.].

[13] The pesticidal active compound is a compound represented by the following formula (I-1ba): [In the formula, R ｈ represents an alkyl group. ｉ may be the same or different and each independently represent a hydrogen atom, a halogen atom, or a monovalent group which may contain one or more heteroatoms. L represents an alkylene group which may have a substituent, and the alkylene group contains one or more -CH ２ The liquid pesticide composition according to any one of [2] to

[10] , wherein - may be substituted with -O-, -S-, -C(=O)-, -C(=S)-, or -N(R)- (wherein R represents a hydrogen atom or a monovalent group). Z represents a C-H or N atom.

[14] The compound represented by formula (I-1ba) is a compound represented by the following formula (I-1ba'): [In the formula, R ｈ represents an alkyl group. ｊ represents a monovalent group which may contain one or more heteroatoms. Z represents a C—H or N atom.] The liquid pesticide composition according to

[13] ,

[0007] It is possible to provide a pesticide composition containing an auxin herbicide, particularly a dicamba amine salt, and another specific pesticidal active compound, which can suppress the volatilization of the auxin herbicide and the decomposition of the specific pesticidal active compound.

[0008] FIG. 1 is a cross-sectional view showing an evaluation device used in Test Example 3.

[0009] <Liquid pesticide composition> The liquid pesticide composition of the present invention (hereinafter also referred to simply as "pesticide composition") contains an auxin herbicide, a pesticidal active compound having a partial structure represented by formula (I) (hereinafter also referred to as "compound (I)"), and at least one selected from the group consisting of polycarboxylic acids and salts thereof. The pesticide composition is usually a pesticide formulation, and its form is not particularly limited as long as it is liquid. "Liquid" means that it exhibits fluidity at 25°C. The pesticide composition can contain an aqueous phase, and preferably contains an aqueous phase and an oil phase. The components that the pesticide composition contains or can contain will be described in detail below.

[0010] [1] Auxin herbicides and agriculturally acceptable salts or esters thereof Examples of auxin herbicides include benzoic acid herbicides and phenoxy herbicides.

[0011] Benzoic acid herbicides include dicamba and agriculturally acceptable salts or esters thereof. In a preferred embodiment, the pesticide composition contains a dicamba amine salt. Examples of dicamba amine salts include dicamba diglycolamine salt, dicamba monoethanolamine salt, dicamba tetrabutylamine salt, dicamba tetrabutylphosphonium salt, dicamba N,N-bis(3-aminopropyl)methylamine (BAPMA) salt, and dicamba choline salt. The dicamba amine salt preferably contains at least one dicamba amine salt selected from dicamba diglycolamine salt and dicamba monoethanolamine salt, and more preferably contains dicamba diglycolamine salt. In one embodiment, the pesticide composition contains one or more dicamba amine salts. A portion of the dicamba amine salt may exist in a neutral state in the pesticide composition. That is, the carboxylate group (-COO) of the dicamba amine salt may be present in a neutral state. － The dicamba amine salt may be present in equilibrium with a carboxy group (—COOH group). In the pesticide composition, the dicamba amine salt is usually dissolved in the aqueous phase.

[0012] When the total amount of the pesticide composition is taken as 100% by mass, the content of the dicamba amine salt in the pesticide composition is preferably 0.1% by mass to 80% by mass, more preferably 0.5% by mass to 70% by mass, even more preferably 1% by mass to 60% by mass, still more preferably 2% by mass to 50% by mass, and particularly preferably 5% by mass to 30% by mass. The content of the dicamba amine salt referred to here is the content as dicamba acid.

[0013] When the pesticide composition contains two or more dicamba amine salts, the content of the dicamba amine salt mentioned above is the total content of the two or more dicamba amine salts. The same applies to other components that the pesticide composition contains or may contain, and when two or more components are contained, the content and concentration of the components are the total content and concentration of the components, unless otherwise specified.

[0014] The concentration of the dicamba amine salt in the pesticide composition is usually from 0.1 mol / L to 5 mol / L, preferably from 0.2 mol / L to 4.5 mol / L, more preferably from 0.3 mol / L to 4 mol / L, even more preferably from 0.4 mol / L to 3.5 mol / L, and still more preferably from 0.5 mol / L to 3 mol / L. The concentration of the dicamba amine salt in the pesticide composition is the value (mol / L) obtained by dividing the weight of the dicamba amine salt contained in the pesticide composition by its molecular weight (mol number), divided by the volume (L) of the pesticide composition.

[0015] Phenoxy herbicides include 2,4-D and its agriculturally acceptable salts or esters. In a preferred embodiment, the pesticide composition contains a 2,4-D amine salt. Examples of 2,4-D amine salts include 2,4-D ammonium salt, 2,4-D diethylammonium salt, 2,4-D dimethylammonium salt, 2,4-D diolamine salt, 2,4-D dodecylammonium salt, 2,4-D heptylammonium salt, 2,4-D isopropylammonium salt, 2,4-D tetradecylammonium salt, 2,4-D triethylammonium salt, 2,4-D tris(2-hydroxypropyl)ammonium salt, 2,4-D trolamine salt, and 2,4-D choline salt. In one embodiment, the pesticide composition contains one or more 2,4-D amine salts. A portion of the 2,4-D amine salt may exist in a neutral state in the pesticide composition. That is, the carboxylate group (—COO ) of the 2,4-D amine salt may be present in a neutral state. － The 2,4-D amine salt may be present in equilibrium with a carboxy group (—COOH group). In the pesticide composition, the 2,4-D amine salt is usually dissolved in the aqueous phase. The content and concentration of the 2,4-D amine salt in the pesticide composition are equivalent to the content and concentration of the dicamba amine salt.

[0016] [2] Compound (I) Compound (I) is a compound having a partial structure represented by formula (I): —C(═O)—X— (I).

[0017] In the pesticide composition, compound (I) may be contained in the aqueous phase or the oil phase, or in a case where the pesticide composition contains two or more types of compound (I), compound (I) may be contained in both the aqueous phase and the oil phase.

[0018] In formula (I), X represents an oxygen atom and NR １ and R represents at least one selected from the group consisting of １represents a monovalent group. That is, compound (I) is a compound having one or more structures selected from the group consisting of ester structures and amide structures. Compound (I) may have two or more ester structures, may have two or more amide structures, or may have one or more ester structures and one or more amide structures. In addition, the pesticide composition may contain two or more types of compound (I).

[0019] R １ Examples of the monovalent group represented by the formula (I) include a hydrogen atom, a monovalent aliphatic (including alicyclic; the same applies hereinafter) group, a monovalent aromatic group, and a monovalent group consisting of a combination of an aliphatic structure and an aromatic structure. Preferably, it is a monovalent aliphatic group, a monovalent aromatic group, or a monovalent group consisting of a combination of an aliphatic structure and an aromatic structure. More preferably, it is a monovalent aromatic group or a monovalent group consisting of a combination of an aliphatic structure and an aromatic structure. The monovalent aliphatic group, the monovalent aromatic group, and the monovalent group consisting of a combination of an aliphatic structure and an aromatic structure may each have one or more substituents and may contain one or more heteroatoms. For example, one or more -CH contained in these monovalent groups ２ - may be substituted by -O-, -S-, -C(=O)-, -C(=S)-, or -N(R)- (wherein R represents a hydrogen atom or a monovalent group).

[0020] The liquid pesticide composition of the present invention, when containing a dicamba amine salt as an auxin herbicide, can inhibit the volatilization of dicamba and inhibit the decomposition of compound (I). The decomposition of compound (I) typically involves cleavage of the C-X bond in formula (I). The decomposition of compound (I) is usually accompanied by the dicamba amine salt present in the pesticide composition. The decomposition of compound (I) refers to the cleavage of at least one bond present in compound (I) and also includes the addition of another atom or molecule to the cleaved site.

[0021] Compound (I) is preferably a herbicidally active compound. Examples of herbicidally active compounds include protoporphyrinogen oxidase (PPO) inhibitors, acetyl CoA carboxylate (ACCase) inhibitors, acetolactate synthase (ALS) inhibitors, acetohydroxyacid synthase (AHAS) inhibitors, photosystem I inhibitors, photosystem II inhibitors, carotenoid biosynthesis inhibitors, enolpyruvylshikimate triphosphate (EPSP) synthase inhibitors, glutamine synthase inhibitors, dihydropteroate synthase inhibitors, mitosis inhibitors, and nucleic acid inhibitors. Among these, compound (I) preferably contains a PPO inhibitor, and more preferably consists of a PPO inhibitor.

[0022] Compound (I) includes, for example, compounds represented by the following formula (I-1): (hereinafter, also referred to as "compound (I-1)").

[0023] In formula (I-1), X has the same meaning as above. ２ represents a monovalent group. ３ represents a monovalent group when X is an oxygen atom, and １ When C(=O)-R ４ Represents R ４ represents a monovalent group, and R ２ and R ４ And, R ２ the carbon atoms bonded to X and R ４ may form a ring together with the carbon atom to which it is bonded.

[0024] R ２ , R ３ , R ４ Examples of the monovalent groups represented by the formula (I) include, independently of one another, monovalent aliphatic groups, monovalent aromatic groups, and monovalent groups consisting of a combination of an aliphatic structure and an aromatic structure. The monovalent aliphatic groups, monovalent aromatic groups, and monovalent groups consisting of a combination of an aliphatic structure and an aromatic structure may each have one or more substituents and may contain one or more heteroatoms. ２ is preferably a monovalent group consisting of a combination of an aliphatic structure and an aromatic structure. When X is an oxygen atom, R ３The monovalent group represented by R is preferably a monovalent aliphatic group, more preferably an alkyl group, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms. ４ The monovalent group represented by the formula (I) is preferably a monovalent aliphatic group or a monovalent group consisting of a combination of an aliphatic structure and an aromatic structure.

[0025] The monovalent aliphatic group, the monovalent aromatic group, and the monovalent group consisting of a combination of an aliphatic structure and an aromatic structure may each have one or more substituents and may contain one or more heteroatoms. For example, one or more —CH ２ - may be substituted by -O-, -S-, -C(=O)-, -C(=S)-, or -N(R)- (wherein R represents a hydrogen atom or a monovalent group).

[0026] X is an oxygen atom, and R ３ The compound (I-1) in which X is a monovalent group is a compound having an ester structure. １ and R ３ is C(=O)-R ４ The compound (I-1) represented by the formula (I-1) is a compound having an imide structure. The compound having an imide structure may be a compound having a uracil ring structure. The uracil ring structure contains an imide structure. The compound having a uracil ring structure is a compound represented by the formula (I-1) represented by the formula (I-1) ２ and R ４ And, R ２ the carbon atoms bonded to X and R ４ and R ２ and R ４ and together, -N(R ａ )-C(R ｂ ) = C(R ｃ )- is formed. ａ , R ｂ , R ｃ are each independently a hydrogen atom or a monovalent group.

[0027] [2-1] Compound Having an Imide Structure Examples of the compound (I-1) having an imide structure include compounds represented by the following formula (I-1a): (hereinafter, also referred to as "compound (I-1a)").

[0028] In formula (I-1a), R １ , R ２ , R ４ has the same meaning as above. １ is preferably an aryl group or heteroaryl group which may have one or more substituents, more preferably a phenyl group or pyridyl group which may have one or more substituents, and even more preferably a phenyl group or 2-pyridyl group which may have one or more substituents. Examples of the substituent include a monovalent group which may contain one or more heteroatoms, a halogen atom, and the like. The halogen atom is a fluorine atom, chlorine atom, bromine atom, or iodine atom, and is preferably a fluorine atom or a chlorine atom.

[0029] R ２ , R ４ Examples of the monovalent groups represented by the formula (I) include, independently of one another, monovalent aliphatic groups, monovalent aromatic groups, and monovalent groups consisting of a combination of an aliphatic structure and an aromatic structure. The monovalent aliphatic groups, monovalent aromatic groups, and monovalent groups consisting of a combination of an aliphatic structure and an aromatic structure may each have one or more substituents and may contain one or more heteroatoms. ２ The monovalent group represented by R is preferably a monovalent group consisting of a combination of an aliphatic structure and an aromatic structure. ４ The monovalent group represented by R is preferably a monovalent aliphatic group or a monovalent group consisting of a combination of an aliphatic structure and an aromatic structure. ２ and R ４ That is, R ２ The carbon atom, N atom, and R bonded to ４ may form a ring together with the carbon atom to which it is bonded.

[0030] The monovalent aliphatic group, the monovalent aromatic group, and the monovalent group consisting of a combination of an aliphatic structure and an aromatic structure may each have one or more substituents and may contain one or more heteroatoms. For example, one or more —CH ２- may be substituted by -O-, -S-, -C(=O)-, -C(=S)-, or -N(R)- (wherein R represents a hydrogen atom or a monovalent group).

[0031] In one preferred embodiment, the compound (I-1a) has the following formula (I-1aa): (hereinafter also referred to as "compound (I-1aa)").

[0032] In formula (I-1aa), R ２ , R ４ has the same meaning as above. ２ and R ４ That is, R ２ The carbon atom, N atom, and R bonded to ４ may form a ring together with the carbon atom bonded to R ｄ represents a fluorine atom or a hydrogen atom. ｅ represents a monovalent group which may contain one or more heteroatoms. ｆ represents a monovalent group which may contain one or more heteroatoms or a halogen atom. ｆ and R ｅ may be taken together to form a ring. Z represents C—H or N (nitrogen atom). The halogen atom is a fluorine atom, chlorine atom, bromine atom or iodine atom, and is preferably a chlorine atom.

[0033] R ｅ A preferred example of the monovalent group which may contain one or more heteroatoms is —Y—R ｇ Y represents an oxygen atom or a sulfur atom, and R ｇ represents a pyridyl group which may have one or more substituents.

[0034] In another preferred embodiment, the compound (I-1a) is a compound having a uracil ring structure. The uracil ring structure includes an imide structure. Examples of the compound (I-1a) having a uracil ring structure include compounds represented by the following formula (I-1ab): (hereinafter, also referred to as "compound (I-1ab)").

[0035] In formula (I-1ab), R １ , Rａ , R ｂ , R ｃ has the same meaning as above. １ is preferably an aryl group or heteroaryl group which may have one or more substituents, more preferably a phenyl group or pyridyl group which may have one or more substituents, and even more preferably a phenyl group or 2-pyridyl group which may have one or more substituents. Examples of the substituent include a monovalent group which may contain one or more heteroatoms, a halogen atom, and the like. The halogen atom is a fluorine atom, chlorine atom, bromine atom, or iodine atom, and is preferably a fluorine atom or a chlorine atom.

[0036] R ａ , R ｂ is preferably a monovalent group, more preferably an alkyl group or amino group optionally substituted with a halogen atom, even more preferably an alkyl group having 1 to 4 carbon atoms optionally substituted with a halogen atom, still more preferably an alkyl group having 1 or 2 carbon atoms optionally substituted with a halogen atom, and particularly preferably a methyl group optionally substituted with a halogen atom. The halogen atom is a fluorine atom, chlorine atom, bromine atom, or iodine atom, preferably a fluorine atom. In one embodiment, R ａ is an alkyl group not substituted with a halogen atom, and R ｂ is a perfluoroalkyl group. The number of carbon atoms in the alkyl group and the perfluoroalkyl group is preferably 1 to 4, more preferably 1 or 2, and even more preferably 1. ｃ is a hydrogen atom or an alkyl group, preferably a hydrogen atom.

[0037] A preferred example of compound (I-1ab) is R １ is a phenyl group or a pyridyl group which may have one or more substituents, and R ａ is a methyl group, and R ｂ is a trifluoromethyl group.

[0038] An example of compound (I-1ab) is a compound represented by the following formula (I-1ab') (hereinafter also referred to as "compound (I-1ab')").

[0039] In formula (I-1ab'), R ｄ , R ｅ , R ｆ has the same meaning as above. Specifically, R ｄ represents a fluorine atom or a hydrogen atom. ｅ represents a monovalent group which may contain one or more heteroatoms. ｆ represents a monovalent group which may contain one or more heteroatoms or a halogen atom. ｆ and R ｅ may be taken together to form a ring. Z represents C—H or N (nitrogen atom). The halogen atom is a fluorine atom, chlorine atom, bromine atom or iodine atom, and is preferably a fluorine atom or chlorine atom.

[0040] R ｅ A preferred example of the monovalent group which may contain one or more heteroatoms is —Y—R ｇ Y represents an oxygen atom or a sulfur atom, and R ｇ represents a pyridyl group which may have one or more substituents.

[0041] A specific example of compound (I-1ab') is a compound represented by the following formula (IA) (hereinafter also referred to as "compound (IA)"), which is a PPO inhibitor.

[0042]

[0043] Examples of compound (I-1aa) other than compounds having a uracil ring structure include a compound represented by the following formula (I-1aa′) (hereinafter also referred to as “compound (I-1aa′)”).

[0044] In formula (I-1aa′), the ring containing the N atom represents a cyclic imide structure. ｄ , R ｅ , R ｆ has the same meaning as above. Specifically, R ｄrepresents a fluorine atom or a hydrogen atom. ｅ represents a monovalent group which may contain one or more heteroatoms. ｆ represents a monovalent group which may contain one or more heteroatoms or a halogen atom. ｆ and R ｅ may be taken together to form a ring. Z represents C—H or N (nitrogen atom). The halogen atom is a fluorine atom, chlorine atom, bromine atom, or iodine atom, and is preferably a chlorine atom. Examples of cyclic imide structures include a succinimide structure, a glutarimide structure, a phthalimide structure, and a tetrahydrophthalimide structure.

[0045] R ｅ A preferred example of the monovalent group which may contain one or more heteroatoms is —Y—R ｇ Y represents an oxygen atom or a sulfur atom, and R ｇ represents a pyridyl group which may have one or more substituents.

[0046] Specific examples of compound (I-1aa') are compounds represented by the following formulae (IB) and (IC) (hereinafter also referred to as "compounds (IB)" and (IC)"), both of which are PPO inhibitors.

[0047]

[0048] [2-2] Compound Having an Ester Structure The compound (I-1) having an ester structure is a compound represented by the following formula (I-1b) (hereinafter also referred to as "compound (I-1b)").

[0049] In formula (I-1b), R ２ , R ３ has the same meaning as above. ２ , R ３ Examples of the monovalent groups represented by the formula (I) include, independently of one another, monovalent aliphatic groups, monovalent aromatic groups, and monovalent groups consisting of a combination of an aliphatic structure and an aromatic structure. The monovalent aliphatic groups, monovalent aromatic groups, and monovalent groups consisting of a combination of an aliphatic structure and an aromatic structure may each have one or more substituents and may contain one or more heteroatoms.２ The monovalent group represented by R is preferably a monovalent group consisting of a combination of an aliphatic structure and an aromatic structure. ３ The monovalent group represented by the formula (I) is preferably a monovalent aliphatic group, more preferably an alkyl group, still more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.

[0050] The monovalent aliphatic group, the monovalent aromatic group, and the monovalent group consisting of a combination of an aliphatic structure and an aromatic structure may each have one or more substituents and may contain one or more heteroatoms. For example, one or more —CH ２ - may be substituted by -O-, -S-, -C(=O)-, -C(=S)-, or -N(R)- (wherein R represents a hydrogen atom or a monovalent group).

[0051] An example of compound (I-1b) is a compound represented by the following formula (I-1ba) (hereinafter also referred to as "compound (I-1ba)").

[0052] In formula (I-1ba), R ｈ represents an alkyl group. ｈ is preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably an alkyl group having 1 or 2 carbon atoms. ｉ may be the same or different and each independently represent a hydrogen atom, a halogen atom, or a monovalent group which may contain one or more heteroatoms. L represents an alkylene group which may have a substituent. The alkylene group contains one or more -CH ２ - may be substituted with -O-, -S-, -C(=O)-, -C(=S)-, or -N(R)- (wherein R represents a hydrogen atom or a monovalent group). The alkylene group has, for example, 2 to 6 carbon atoms, and preferably 2 or 3. Examples of the substituent that the alkylene group may have include a halogen atom. Z represents C-H or N (nitrogen atom).

[0053] A preferred example of compound (I-1ba) is a compound represented by the following formula (I-1ba') (hereinafter also referred to as "compound (I-1ba')").

[0054] In formula (I-1ba'), R ｈ , Z has the same meaning as above. ｊ represents a monovalent group which may contain one or more heteroatoms.

[0055] Specific examples of compound (I-1ba') are the above-mentioned compound (IA) and compound (IC), both of which are PPO inhibitors.

[0056] When the total amount of the pesticide composition is taken as 100% by mass, the content of compound (I) in the pesticide composition is preferably 0.01% by mass or more and 25% by mass or less, more preferably 0.05% by mass or more and 20% by mass or less, even more preferably 0.1% by mass or more and 15% by mass or less, and still more preferably 0.2% by mass or more and 10% by mass or less, from the viewpoint of improving the storage stability of the pesticide composition while appropriately increasing the content.

[0057] [3] Other pesticidal active compounds The pesticidal composition may contain one or more pesticidal active compounds other than the auxin herbicide and compound (I). The pesticidal active compounds other than the auxin herbicide and compound (I) are not particularly limited and include insecticidal active ingredients, fungicidal active ingredients, herbicidal active ingredients, plant growth regulating active ingredients, and phytotoxicity safening active ingredients, with herbicidal active ingredients being preferred.

[0058] Examples of herbicidally active compounds include protoporphyrinogen oxidase (PPO) inhibitors, acetyl CoA carboxylate (ACCase) inhibitors, acetolactate synthase (ALS) inhibitors, acetohydroxyacid synthase (AHAS) inhibitors, photosystem I inhibitors, photosystem II inhibitors, carotenoid biosynthesis inhibitors, enolpyruvylshikimate triphosphate (EPSP) synthase inhibitors, glutamine synthase inhibitors, dihydropteroate synthase inhibitors, mitosis inhibitors, and nucleic acid inhibitors.

[0059] When the total amount of the pesticidal active compounds contained in the pesticidal composition is taken as 100% by mass, the total content of the auxin herbicide and compound (I) in all the pesticidal active compounds contained in the pesticidal composition is, for example, 50% by mass or more and 100% by mass or less, preferably 60% by mass or more and 100% by mass or less, more preferably 80% by mass or more and 100% by mass or less, even more preferably 90% by mass or more and 100% by mass or less, and particularly preferably 95% by mass or more and 100% by mass or less.

[0060] [4] Polycarboxylic Acid and Salt Thereof The pesticide composition contains at least one selected from the group consisting of polycarboxylic acids and their salts. In this specification, "polycarboxylic acid" refers to a compound having two or more carboxy groups in one molecule. Hereinafter, polycarboxylic acids and polycarboxylates are collectively referred to as "polycarboxylic acids." The pesticide composition according to the present invention, which contains polycarboxylic acids, can suppress the volatilization of auxin herbicides and the decomposition of Compound (I). In contrast, when a monocarboxylic acid or its salt is used instead of polycarboxylic acids, the volatilization of auxin herbicides can be suppressed, but the decomposition of Compound (I) cannot be suppressed. The pesticide composition may contain two or more polycarboxylic acids, two or more polycarboxylates, or one or more polycarboxylic acids and one or more polycarboxylates.

[0061] In the polycarboxylate, all of the carboxy groups may be in the form of a salt, or some of the carboxy groups may be in the form of a salt. － M ＋ and M ＋ is a cation. Examples of the polycarboxylic acid salt include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as magnesium salt and calcium salt, and amine salts.

[0062] The polycarboxylic acids and polycarboxylates are preferably polymers (including oligomers). A polymer is a compound having one or more carboxy groups or —COO groups. － M ＋Hereinafter, a polymer of polycarboxylic acid will also be referred to as a "polycarboxylic acid polymer," and a polymer of polycarboxylate will also be referred to as a "polycarboxylate polymer." Polycarboxylic acid polymers and polycarboxylate polymers are polymers of monomers having carboxy groups and / or -COO groups. － M ＋ The polycarboxylic acid polymer and the polycarboxylate polymer have 2 or more carboxy groups and -COO groups, and preferably 10 or more carboxy groups. － M ＋ The number of groups depends on the molecular weight (degree of polymerization) of the polymer.

[0063] Polycarboxylic acid polymers and polycarboxylate polymers contain carboxy groups or -COO － M ＋ It may be a homopolymer of a monomer having a carboxy group or a —COO group. － M ＋ The polycarboxylic acid polymer and the polycarboxylate polymer may be a copolymer of a monomer having a group and another monomer copolymerizable therewith. The polycarboxylic acid polymer and the polycarboxylate polymer are preferably water-soluble.

[0064] Carboxy group or -COO － M ＋ Examples of monomers having a group include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexene dicarboxylic acid; and salts thereof. Polycarboxylic acid polymers and polycarboxylate polymers can be prepared by adding a carboxy group or a —COO － M ＋ The copolymer may contain two or more types of structural units derived from monomers having a group.

[0065] Examples of the other monomers include acrylic acid esters, methacrylic acid esters, vinyl alcohol, acrylamide, etc. The polycarboxylic acid polymer and the polycarboxylate polymer may contain two or more types of structural units derived from the other monomers.

[0066] Examples of polycarboxylic acid polymers and polycarboxylic acid salt polymers include polyacrylic acid, polymethacrylic acid, alkali metal salts of polyacrylic acid or polymethacrylic acid (sodium salts, potassium salts, etc.), acrylic acid-maleic acid copolymer, methacrylic acid-maleic acid copolymer, alkali metal salts of acrylic acid-maleic acid copolymer or methacrylic acid-maleic acid copolymer (sodium salts, potassium salts, etc.), and the like.

[0067] The molecular weight (Mw) of the polycarboxylic acid polymer and the polycarboxylate polymer is preferably 200 or more, more preferably 500 or more, even more preferably 1000 or more, even more preferably 1200 or more, even more preferably 1500 or more, even more preferably 2000 or more, particularly preferably 2500 or more, and most preferably 4000 or more. When the Mw is within the above range, the decomposition of compound (I) can be effectively suppressed. Furthermore, the Mw is preferably 250,000 or less, more preferably 200,000 or less, even more preferably 150,000 or less, even more preferably 100,000 or less, even more preferably 75,000 or less, even more preferably 50,000 or less, particularly preferably 30,000 or less, and most preferably 25,000 or less. When the Mw is within the above range, the polycarboxylic acid polymer and the polycarboxylate polymer are easily water-soluble, thereby facilitating the preparation of formulations.

[0068] When the auxin herbicide contained in the pesticide composition is a dicamba amine salt, the content of polycarboxylic acids in the pesticide composition, when the amount of dicamba amine salt is expressed as the amount of dicamba acid constituting it and the amount of polycarboxylic acids is expressed as the amount of one molecule of monocarboxylic acid constituting it, is preferably 0.1 mol to 10 mol, more preferably 0.2 mol to 8 mol, even more preferably 0.3 mol to 6 mol, still more preferably 0.4 mol to 4 mol, and particularly preferably 0.5 mol to 2 mol, per mol of dicamba acid. When the content of polycarboxylic acids is within the above range, the decomposition of compound (I) can be effectively inhibited while appropriately suppressing the volatility of dicamba.

[0069] [5] Basic Component The pesticide composition may further contain a basic component. The basic component can function as a pH adjuster for adjusting the pH of the pesticide composition. The basic component is preferably water-soluble. The pesticide composition may contain two or more basic components. Note that the basic component referred to here does not include the above-mentioned polycarboxylates that exhibit basicity.

[0070] Examples of basic components include organic bases such as diglycolamine, monoethanolamine, and polyethyleneimine, as well as inorganic bases. The basic component is preferably an inorganic base, and more preferably an alkali metal salt. Examples of alkali metal salts include alkali metal hydroxides, alkali metal carbonates, and alkali metal bicarbonates. Among these, the basic component is preferably an alkali metal hydroxide. Examples of alkali metal hydroxides include lithium hydroxide, sodium hydroxide, and potassium hydroxide, with sodium hydroxide and potassium hydroxide being preferred. When the pesticide composition further contains a basic component, it is preferable that the pesticide composition contains at least one alkali metal hydroxide selected from the group consisting of potassium hydroxide and sodium hydroxide.

[0071] The content of the basic component in the pesticide composition is preferably adjusted taking into account the pH value of the pesticide composition. The pH value of the pesticide composition at 25°C is preferably 4.0 to 9.0, more preferably 4.2 to 8.5, even more preferably 4.4 to 8.0, even more preferably 4.6 to 7.5, even more preferably 4.7 to 7.0, even more preferably 4.8 to 6.5, even more preferably 4.9 to 6.0, and most preferably 5.0 to 5.8. When the pH value of the pesticide composition at 25°C is within the above range, the decomposition of compound (I) can be more effectively suppressed. The pH value of the pesticide composition can be measured by placing the pesticide composition in a glass container, shaking it by hand, and then immersing the electrodes of a pH meter in the pesticide composition.

[0072] The content of the basic component in the pesticide composition is preferably an amount such that the pH value of the pesticide composition at 25° C. is within the above range. The concentration of the basic component in the pesticide composition is, for example, 0.0001 mol / L to 0.050 mol / L, preferably 0.0005 mol / L to 0.040 mol / L, more preferably 0.00075 mol / L to 0.030 mol / L, even more preferably 0.001 mol / L to 0.025 mol / L, and more preferably 0.002 mol / L to 0.020 mol / L.

[0073] The pesticide composition may not contain a basic component. An example of a pesticide composition that does not contain a basic component is a pesticide composition in which the pH value at 25°C of the pesticide composition is adjusted to fall within the above range by containing polycarboxylic acids. For example, by using a polycarboxylic acid and a polycarboxylate in combination as the polycarboxylic acids, the pH value at 25°C of the pesticide composition can be adjusted to fall within the above range without further containing a basic component.

[0074] [6] Organic Solvent The pesticide composition may contain an organic solvent. The organic solvent constitutes the oil phase. The organic solvent is preferably an organic solvent capable of dissolving compound (I). The pesticide composition may contain one or more organic solvents.

[0075] The organic solvent preferably has a water solubility of 10% by mass or less at 25°C. The water solubility may be 8% by mass or less, 5% by mass or less, 3% by mass or less, or even 1% by mass or less. It is preferable that the pesticide composition contains an organic solvent having a water solubility within this range, since this improves the storage stability of the pesticide composition. The water solubility of the organic solvent at 25°C is usually 0% by mass or more, and 10% by mass or less. －５ It may be % by mass or more.

[0076] In this specification, the water solubility at 25°C refers to the solubility in water at a temperature of 25°C and a pH of 7. For example, a water solubility of 10% by mass at 25°C means that the solubility in 1 g of water at a temperature of 25°C and a pH of 7 is 1 x 10 －１ This means that it is g.

[0077] The water solubility of an organic solvent can be determined from the values ​​listed in the Solubility Database of the International Union of Pure and Applied Chemistry (IUPAC) or the National Institute of Standards and Technology (NIST). If the value is not listed in the database, the water solubility of the organic solvent can be measured by quantifying the saturated solubility in water at 25°C and pH 7 using high performance liquid chromatography.

[0078] Examples of organic solvents capable of dissolving compound (I) include alcohols such as butanol, amyl alcohol, hexanol, heptanol, octanol, 2-ethylhexanol, cyclohexanol, and benzyl alcohol; Esters such as acetate esters (e.g., ethyl acetate, butyl acetate, isoamyl acetate, isobornyl acetate, hexyl acetate, heptyl acetate, octyl acetate, benzyl acetate), carbonate esters (e.g., diethyl carbonate, dibutyl carbonate), fatty acid esters (e.g., isopropyl myristate, methyl octanoate, methyl oleate, methyl laurate, dimethyl adipate, dibutyl adipate, didecyl adipate, tri-n-butyl citrate, di-n-butyl phthalate, methyl caprylate, methyl laurate, methyl myristate, methyl salicylate, methyl palmitate, methyl oleate, ethyl palmitate), phthalate esters (e.g., dimethyl phthalate, diethyl phthalate), benzoate esters (e.g., methyl benzoate, ethyl benzoate), succinate esters (e.g., dioctyl succinate), acetoacetate esters (e.g., tert-butyl acetoacetate, allyl acetoacetate); ethers such as propylene glycol phenyl ether; Ketones such as cyclohexanone, 2-heptanone, isophorone, mesityl oxide, methyl isoamyl ketone, methyl isobutyl ketone, acetophenone, methylcyclohexanone, and acetophenone; amides such as fatty acid dimethylamides (e.g., N,N-dimethyloctaneamide, N,N-dimethyldecanamide, N,N-dimethyldodecanamide, N,N-dimethyltetradecaneamide, and N,N-dimethyloctadecaneamide) and alkylpyrrolidones (e.g., N-octylpyrrolidone, N-dodecylpyrrolidone, and N-decylpyrrolidone); lactones such as γ-octanolactone and δ-octanolactone; amines such as n-octylamine, oleylamine, and laurylamine; aliphatic hydrocarbons such as decane, tridecane, tetradecane, hexadecane, octadecane, normal paraffins, isoparaffins, cycloparaffins, 1-undecene, and 1-heneicosene;aromatic hydrocarbons such as toluene, xylene, ethylbenzene, octadecylbenzene, alkylbenzenes such as dialkylbenzenes and trialkylbenzenes, alkylnaphthalenes such as methylnaphthalene, dimethylnaphthalene, dodecylnaphthalene and tridecylnaphthalene, phenylxylylethane and 1-phenyl-1-ethylphenylethane, and mixtures thereof; fatty acids such as oleic acid, capric acid and enanthic acid; animal and vegetable oils such as coconut oil, olive oil, soybean oil, rapeseed oil, castor oil, linseed oil, cottonseed oil, palm oil, avocado oil, shark liver oil, sardine oil and saury oil; mineral oils such as naphtha, petroleum ether, kerosene, diesel oil, paraffin, olefin and machine oil; silicone oil;

[0079] From the viewpoint of the solubility of Compound (I) and the storage stability of the pesticide composition, the organic solvent preferably comprises one or more selected from the group consisting of aromatic hydrocarbons, aliphatic hydrocarbons, ketones, esters, ethers, amides, amines, and alcohols, and more preferably comprises an aromatic hydrocarbon. The aromatic hydrocarbon preferably comprises one or more selected from the group consisting of alkylbenzenes (e.g., toluene, xylene, ethylbenzene, octadecylbenzene, dialkylbenzenes, and trialkylbenzenes), alkylnaphthalenes (e.g., methylnaphthalene, dimethylnaphthalene, dodecylnaphthalene, and tridecylnaphthalene), phenylxylylethane, and 1-phenyl-1-ethylphenylethane, more preferably one or more selected from the group consisting of alkylbenzenes and alkylnaphthalenes, and even more preferably one or more selected from the group consisting of C9-C12 alkylbenzenes and C10-C15 alkylnaphthalenes. The organic solvent may consist of an aromatic hydrocarbon.

[0080] When the total amount of the pesticide composition is taken as 100% by mass, the content of the organic solvent in the pesticide composition is preferably from 0.1 to 45% by mass, more preferably from 0.5 to 40% by mass, even more preferably from 1 to 35% by mass, and still more preferably from 3 to 30% by mass. It is preferable for the pesticide composition to contain the organic solvent at a content within this range, from the viewpoint of appropriately increasing the content of compound (I) and improving the storage stability of the pesticide composition.

[0081] The content of the organic solvent is usually 1 to 50 times by mass, preferably 2 to 40 times by mass, more preferably 3 to 30 times by mass, even more preferably 4 to 25 times by mass, still more preferably 5 to 20 times by mass, even more preferably 6 to 20 times by mass, still more preferably 7 to 20 times by mass, and particularly preferably 8 to 20 times by mass. Adjusting the ratio (mass ratio) of the content of the organic solvent to the content of compound (I) within this range is preferred from the viewpoint of improving the storage stability of the pesticide composition while appropriately increasing the content of compound (I).

[0082] [7] Water The pesticide composition may contain water. Examples of water include ion-exchanged water, tap water, and groundwater. Water constitutes the aqueous phase of the pesticide composition.

[0083] When the total amount of the pesticide composition is taken as 100% by mass, the water content in the pesticide composition is preferably 30% by mass to 95% by mass, more preferably 35% by mass to 90% by mass, even more preferably 40% by mass to 80% by mass, and still more preferably 45% by mass to 75% by mass. It is preferable for the pesticide composition to contain water at a content within this range from the viewpoint of improving the suspension or emulsification state of the pesticide composition.

[0084] [8] Other Components The pesticide composition may contain formulation adjuvants, such as surfactants, thickeners, antifoaming agents, antifreeze agents, and preservatives.

[0085] Examples of surfactants include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants. The pesticide composition may contain one or more surfactants selected from the group consisting of nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants.

[0086] Examples of nonionic surfactants include: block polymers such as polyoxyethylene polyoxypropylene block copolymers and block polymers of alkanol, polyethylene oxide, and polypropylene oxide; synthetic polymers such as vinyl acetate copolymers, polymethacrylic acid, and copolymers of methacrylic acid and methacrylic acid esters; polyoxyalkylene fatty acid esters such as polyoxyethylene fatty acid esters (e.g., polyoxyethylene stearate ester), polyoxypropylene fatty acid esters (e.g., polyoxypropylene stearate ester), and polyoxyethylene polyoxypropylene fatty acid esters; fatty acid esters such as polyol fatty acid esters, monoglycerides, and phospholipids; Alcohol ethoxylates such as aliphatic alcohol ethoxylates (e.g., tridecyl alcohol ethoxylate, isooctyl alcohol ethoxylate, lauryl alcohol ethoxylate, hexadecyl alcohol ethoxylate, stearyl alcohol ethoxylate), alkylphenol ethoxylates (e.g., nonylphenol ethoxylate, tristyrylphenol ethoxylate, tributylphenol ethoxylate, octylphenol ethoxylate), arylalkylphenol ethoxylate, arylphenol ethoxylate (e.g., monobenzyl biphenol alcohol ethoxylate); alcohol propylates such as aliphatic alcohol propylate, alkylphenol propylate, arylalkylphenol propylate; polyoxyalkylene vegetable oils such as polyoxyethylene castor oil and polyoxyethylene polyoxypropylene castor oil; polyoxyalkylene hydrogenated vegetable oils such as polyoxyethylene hydrogenated castor oil; glycerin fatty acid esters; glucose esters; cellulose esters; Sucrose fatty acid esters (e.g., sucrose stearate diester); polyvinyl alcohol; sorbitan fatty acid esters (e.g., sorbitan laurate, sorbitan stearate, sorbitan oleate, and sorbitan trioleate);Examples of the alkoxylated amine include polyoxyalkylene sorbitan fatty acid esters (e.g., polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, and polyoxyethylene sorbitan trioleate); fatty acid amine esters such as polyoxyethylene fatty acid amine esters and polyoxypropylene fatty acid amine esters; polyoxyethylene rosin esters; amides such as fatty acid alkanolamides (e.g., lauric acid diethanolamide), alkoxylated propylene oxide fatty acid glucamides, polyoxyethylene oleic acid amide, polyoxyethylene stearic acid amide, and polyvinylpyrrolidone; and amines such as alkoxylated amines (e.g., polyoxyethylene oleylamine, α,α'-[(9-octadecenylimino)di-2,1-ethanedyl]bis(ω-hydroxy)poly(oxyethylene)).

[0087] Examples of anionic surfactants include alkyl sulfonates (e.g., dodecyl sulfonate), alpha olefin sulfonate, alkyl benzene sulfonate (e.g., decyl benzene sulfonate, dodecyl benzene sulfonate, tridecyl benzene sulfonate, diphenyl sulfonate), alkyl naphthalene sulfonate (e.g., naphthalene sulfonate, dibutyl naphthalene sulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonate, diisopropyl naphthalene sulfonate, triisopropyl naphthalene sulfonate), dialkyl sulfosuccinate (e.g., sodium di(2-ethylhexyl) sulfosuccinate), N-methyl-N-acyltaurate (e.g., oleoyl methyl taurate), other sulfonates such as lignin sulfonate, alkyl phenol sulfonate and derivatives thereof, naphthalene sulfonate-formaldehyde condensate and derivatives thereof, and benzimidazole sulfonic acid derivatives; sulfate salts such as alkyl sulfates (e.g., n-hexyl sulfate, n-heptyl sulfate, lauryl sulfate, lauryl sulfate diethanolate, octadecyl sulfate), polyoxyethylene alkyl ether sulfates (e.g., laureth-3 sulfate), polyoxypropylene alkyl ether sulfate, polyoxyethylene distyrylphenyl ether sulfate; carboxylate salts such as fatty acid salts such as octanoate, decanoate, laurate, myristate, palmitate, stearate, behenate, oleate, and derivatives thereof, ether carboxylate salts such as laureth-3-carboxylate, and derivatives thereof, N-acyl sarcosine salts such as N-lauroyl sarcosine salt, and derivatives thereof, N-acyl glutamate salts such as N-lauroyl glutamate, and derivatives thereof, polycarboxylate salts such as polyacrylates, polyvinyl acetates, and comb polymers of polyacid salts, and derivatives thereof; Examples of the phosphate ester salts include alkyl phosphates such as lauryl phosphate and derivatives thereof, polyoxyethylene alkyl ether phosphates and derivatives thereof, polyoxyethylene alkylphenyl ether phosphates and derivatives thereof, and polyoxypropylene alkyl ether phosphates and derivatives thereof.

[0088] Examples of the salts of the sulfonates, sulfates, carboxylates and phosphates include sodium salts, potassium salts, calcium salts, ammonium salts, isopropylamine salts and triethanolamine salts.

[0089] Examples of cationic surfactants include alkylamine salts such as monomethylamine salts, dimethylamine salts, trimethylamine salts, and dodecylamine salts; fatty acid amidoamine salts such as stearamidopropyldimethylamine and behenamidopropyldimethylamine; polyamine salts such as polyvinylamine and polyethyleneimine; and alkyl quaternary ammonium salts such as lauryltrimethylammonium salts, cetyltrimethylammonium salts, dodecyltrimethylammonium salts, stearylmethylammonium salts, benzylbis(2-chloroethyl)ethyl bromide ammonium salts, alkyldimethylbenzylammonium salts, alkylpyridinium salts, alkylisoquinolinium salts, and dialkylmorpholinium salts.

[0090] Examples of amphoteric surfactants include N-laurylalanine, N,N,N-trimethylaminopropionic acid, N,N,N-trihydroxyethylaminopropionic acid, N-hexyl-N,N-dimethylaminoacetic acid, betaine, alkylbetaine (e.g., 1-(2-carboxyethyl)pyrimidinium betaine), imidazoline, taurine, alkyltaurine, and lecithin.

[0091] From the viewpoint of improving the suspension or emulsification state of the pesticide composition, when the total amount of the pesticide composition is taken as 100% by mass, the content of the surfactant in the pesticide composition is preferably 0.5 to 30% by mass, more preferably 0.7 to 25% by mass, even more preferably 0.8 to 20% by mass, still more preferably 1 to 15% by mass, and particularly preferably 1.5 to 10% by mass. The content of the surfactant is preferably 0.05 to 30 times by mass, more preferably 0.07 to 25 times by mass, even more preferably 0.1 to 20 times by mass, and particularly preferably 0.1 to 15 times by mass of the content of the pesticidal active compound.

[0092] Examples of thickeners include polysaccharides such as xanthan gum, guar gum, welan gum, diutan gum, cellulose nanofiber, clay, silicates, etc. When the total amount of the pesticide composition is taken as 100% by mass, the content of the thickener in the pesticide composition is usually 0.01% by mass or more, and may be 0.05% by mass or more, or 0.1% by mass or more, and is usually 5% by mass or less, and may be 3% by mass or less.

[0093]

[0032] When the total amount of the pesticide composition is taken as 100% by mass, the content of the antifoaming agent in the pesticide composition is usually 0.01% by mass or more, and may be 0.05% by mass or more, or 0.1% by mass or more, and is usually 1% by mass or less, and may be 0.5% by mass or less.

[0094] Examples of antifreezing agents include ethylene glycol, propylene glycol, urea, glycerin, etc. When the total amount of the pesticide composition is taken as 100% by mass, the content of the antifreezing agent in the pesticide composition is usually 1% by mass or more, and may be 2% by mass or more, and is usually 10% by mass or less, and may be 8% by mass or less.

[0095] Examples of preservatives include isothiazolinone preservatives. When the total amount of the pesticide composition is taken as 100% by mass, the content of the preservative in the pesticide composition is usually 0.05% by mass or more, and may be 0.1% by mass or more, and is usually 0.5% by mass or less, and may be 0.3% by mass or less.

[0096] <Preparation of Liquid Pesticide Composition> A pesticide composition in the form of a suspension in which a dicamba amine salt is contained in an aqueous phase and Compound (I) is suspended in the aqueous phase can be prepared, for example, as follows. A suspension is obtained by grinding and suspending the dicamba amine salt, Compound (I), water, a surfactant, and, if necessary, other formulation adjuvants, by wet grinding using media such as glass beads or zirconia. The suspension may not contain the dicamba amine salt. If it does not contain the dicamba amine salt, the resulting suspension is mixed with the dicamba amine salt to obtain a mixture. The suspension or mixture is mixed with polycarboxylic acids and, if necessary, a basic component and formulation adjuvants such as a thickener, preservative, and antifoaming agent to obtain a pesticide composition.

[0097] An agrochemical composition that is an oil-in-water emulsion in which the dicamba amine salt is contained in the aqueous phase and Compound (I) is contained in the oil phase can be prepared, for example, as follows: Compound (I), an organic solvent, and, if necessary, a surfactant are mixed to prepare an oil phase. Meanwhile, a dicamba amine salt, formulation adjuvants, water, and, if necessary, a surfactant are added to prepare an aqueous phase. The surfactant may be added to the organic solvent, the water, or both. The oil phase is added to the aqueous phase and emulsified using a stirrer such as a homogenizer to obtain an emulsion. The emulsion is then mixed with polycarboxylic acids and, if necessary, a basic component and formulation adjuvants such as thickeners, preservatives, and antifoaming agents to obtain the agrochemical composition.

[0098] An agrochemical composition that is an oil-in-water emulsion in which the dicamba amine salt is contained in the aqueous phase, compound (I) (first compound (I)) is suspended in the aqueous phase, and another compound (I) (second compound (I)) is contained in the oil phase can be prepared, for example, as follows: The second compound (I), an organic solvent, and optionally a surfactant are mixed to prepare an oil phase. Meanwhile, the dicamba amine salt, formulation adjuvants, water, and optionally a surfactant are added to prepare an aqueous phase. The surfactant may be added to the organic solvent, the water, or both. Furthermore, the first compound (I), water, surfactant, and optionally other formulation adjuvants are milled and suspended by wet milling using media such as glass beads or zirconia to obtain a suspension. The oil phase is added to the aqueous phase and emulsified using a stirrer such as a homogenizer to obtain an emulsion. The emulsion, the suspension, polycarboxylic acids, and, if necessary, a basic component and formulation adjuvants such as a thickener, a preservative, and an antifoaming agent are mixed together to obtain a pesticide composition.

[0099] <Use of Liquid Pesticide Composition> The pesticide composition can be suitably used as a liquid pesticide formulation, which is called in the pesticide field a suspension concentrate (SC), an emulsifiable concentrate (EC), an emulsion oil in water (EW), a suspoemulsion (SE), a microemulsion (ME), a microcapsule (MC), a soluble concentrate (SL), or the like.

[0100] The pesticide composition can be used to control weeds in agricultural land such as farmland, orchard, pasture, lawn, and forestry land; and non-agricultural land such as embankment slopes, riverbeds, road shoulders and slopes, railway beds, park green spaces, sports grounds, parking lots, airports, industrial facility sites such as factories and storage facilities, fallow land, and unused urban land.

[0101] The user typically mixes the pesticide composition with water to prepare a suspension or emulsion, and then applies the suspension or emulsion from a knapsack sprayer, spray tank, spray plane, or irrigation system. The amount to be applied varies depending on weather conditions, treatment time, soil conditions, target crops, target weeds, etc., but is typically 10 to 2,000 L, preferably 50 to 400 L, per hectare. The suspension or emulsion is typically prepared by mixing with water in an amount typically 2 to 10,000 times, preferably 10 to 8,000 times, and more preferably 15 to 6,000 times the volume of the suspension or emulsion, respectively.

[0102] An adjuvant may be mixed in when applying the suspension or emulsion. The type of adjuvant is not particularly limited, but it is preferable to mix an oil-based adjuvant such as Agri-Dex or MSO (a mineral oil such as paraffinic hydrocarbons, naphthenic hydrocarbons, or aromatic hydrocarbons, or a methylated seed oil obtained by esterifying a vegetable oil (soybean oil or rapeseed oil)) in the spray solution at 0.25%, 0.5%, 1%, 2%, 3%, 4%, 5%, or 6% (volume / volume), or a nonionic adjuvant such as Induce (a polyoxyalkylene alkyl ether, polyoxyalkylene fatty acid ester, alkylaryl alkoxylate, or alkylaryl polyoxyalkylene glycol) in the spray solution at 0.05%, 0.1%, 0.25%, or 0.5% (volume / volume). Other examples include anionic (substituted sulfonate) sprays such as Gramine S, cationic (polyoxyethyleneamine) sprays such as Genamin T 200BM, and organic silicone sprays such as Silwet L77. Furthermore, drift reducers such as Intact (polyethylene glycol) and / or volatilization reducers such as Vapex, a VaporGrip Xtra Agent (a mixture of potassium hydroxide and acetic acid) may be used. The pH and hardness of the spray solution are not particularly limited.

[0103] The present invention will be explained in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples.

[0104] The components used in preparing the liquid pesticide composition are shown below.

[0105] [1] Dicamba amine salts Dicamba-DGA: dicamba diglycolamine salt (When preparing the liquid pesticide composition, a 59.0% by mass aqueous solution of this salt (39.5% by mass as dicamba acid) was used. The blending amounts shown in Tables 1 and 2 are the amounts as dicamba acid.) Dicamba-MEA: dicamba monoethanolamine salt (When preparing the liquid pesticide composition, a 71.6% by mass aqueous solution of this salt (56.0% by mass as dicamba acid) was used. The blending amounts shown in Tables 1 and 2 are the amounts as dicamba acid.)

[0106] [2] Compound (I) Compound (IA) represented by the above formula (IA) Compound (IB) represented by the above formula (IB) Compound (IC) represented by the above formula (IC)

[0107] [3] Organic solvent Solvesso 200ND: Aromatic hydrocarbon, mainly C10-C13 alkylnaphthalene, manufactured by ExxonMobil Corporation

[0108] [4] Surfactants Pluronic P-104: polyoxyethylene polyoxypropylene block copolymer, manufactured by BASF Reax 910: lignin sulfonic acid sodium salt, manufactured by Ingevity Synperonic PE / F 127: polyoxyethylene polyoxypropylene block copolymer, manufactured by Croda Selvol 523: polyvinyl alcohol, manufactured by Sekisui Chemical Co., Ltd.

[0109] [5] Thickeners Kelzan AP-AS: xanthan gum, manufactured by CP Kelco Veegum R: magnesium aluminum silicate, manufactured by R. T. Vanderbilt Company, Inc.

[0110] [6] Defoamer XIAMETER ACP-1500: Silicone-based mixture, manufactured by Toray Dow Corning

[0111] [7] Preservative Proxel GXL: 1,2-benzisothiazolin-3-one, manufactured by Lonza

[0112] [8] Other additives NaCl: Sodium chloride (special reagent grade), manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.

[0113] [9] Acids or salts thereof Acetic acid: acetic acid (special reagent grade), manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Propionic acid: propionic acid (Wako special grade), manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Polyacrylic acid 5,000: polyacrylic acid (Wako grade 1), manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Solid content: 100% by mass, weight average molecular weight: 5000 Polyacrylic acid 25,000: polyacrylic acid (Wako grade 1), manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. Solid content: 100% by mass, weight average molecular weight: 25000 AQUALIC TL-37: acrylic acid-maleic acid copolymer sodium salt, manufactured by Nippon Shokubai Co., Ltd. Solid content: 37% by mass, weight average molecular weight: 5000

[0114]

[10] Basic components Potassium hydroxide: potassium hydroxide (purity 85%, special reagent grade), manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. The blending amounts shown in Tables 1 and 2 are pure content equivalents. Sodium hydroxide: sodium hydroxide (purity 97%, special reagent grade), manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. The blending amounts shown in Tables 1 and 2 are pure content equivalents.

[0115] <Preparation of Emulsion (A1) of Pesticide Active Compound Containing Dicamba DGA> 0.53 parts by weight of compound (IA), 1.00 parts by weight of Pluronic P-104, and 5.25 parts by weight of Solvesso 200ND were mixed to prepare 6.775 parts by weight of an oil phase. The oil phase was added to a mixture of 37.21 parts by weight of an aqueous solution of Dicamba DGA (dicamba acid concentration: 39.5% by weight) and 0.067 parts by weight of XIAMETER ACP-1500, and the mixture was stirred and emulsified using a Polytron homogenizer (manufactured by KINEMATICA), to obtain 44.06 parts by weight of an emulsion (A1) of the pesticide active compound.

[0116] <Preparation of Emulsion (A2) of Pesticidal Active Compound Containing Dicamba MEA> 0.53 parts by mass of Compound (IA), 1.00 parts by mass of Pluronic P-104, and 5.25 parts by mass of Solvesso 200ND were mixed to prepare 6.775 parts by mass of an oil phase. The oil phase was added to a mixture of 26.25 parts by mass of an aqueous Dicamba MEA solution (dicamba acid concentration: 56.0% by mass) and 0.067 parts by mass of XIAMETER ACP-1500, and the mixture was stirred and emulsified using a Polytron homogenizer (manufactured by KINEMATICA) to obtain 33.10 parts by mass of Emulsion (A2) of the pesticidal active compound.

[0117] <Preparation of Emulsion (A3) of Pesticide Active Compound Containing Dicamba DGA> 0.53 parts by weight of compound (IA) was mixed with 5.25 parts by weight of Solvesso 200ND to prepare 5.775 parts by weight of an oil phase. 37.21 parts by weight of an aqueous solution of Dicamba DGA (dicamba acid concentration: 39.5% by weight), 0.067 parts by weight of XIAMETER ACP-1500, and 3.89 parts by weight of an aqueous solution of Selvol 523 (Selvol 523 concentration: 9% by weight) was added to the oil phase, and the mixture was stirred and emulsified using a Polytron homogenizer (manufactured by KINEMATICA), to obtain 46.95 parts by weight of an emulsion (A3) of the pesticide active compound.

[0118] <Preparation of suspension (B1) of agricultural chemical active compound containing compound (IB)> To 14.72 parts by mass of ion-exchanged water, 0.40 parts by mass of Veegum R, 0.067 parts by mass of XIAMETER ACP-1500, 4.00 parts by mass of Reax910, 0.50 parts by mass of Synperonic PE / F 127, and 2.28 parts by mass of compound (IB) were added and stirred and mixed, and then wet-pulverized using a bead mill (product name Dyno Mill, manufactured by Shinmaru Enterprises, glass bead diameter 1.0 mm, filling rate 80%, peripheral speed 10 m / s) to obtain 21.97 parts by mass of a suspension (B1) of agricultural chemical active compound.

[0119] <Preparation of Suspension (B2) of Pesticidal Active Compound Containing Compound (IC)> To 14.72 parts by mass of ion-exchanged water, 0.40 parts by mass of Veegum R, 0.067 parts by mass of XIAMETER ACP-1500, 4.00 parts by mass of Reax910, 0.50 parts by mass of Synperonic PE / F 127, and 2.28 parts by mass of Compound (IC) were added, stirred, and mixed. The mixture was wet-pulverized using a bead mill (product name: Awatori Rentaro ARE-310, manufactured by THINKY Corporation) to obtain 21.97 parts by mass of a suspension (B2) of the pesticidal active compound.

[0120] <Preparation of Thickener-Containing Liquid (C1)> 0.20 parts by mass of Kelzan AP-AS, 0.20 parts by mass of Proxel GXL, and 20.00 parts by mass of ion-exchanged water were mixed to obtain 20.40 parts by mass of thickener-containing liquid (C1).

[0121] Preparation of thickener-containing liquid (C2) 20.40 parts by mass of thickener-containing liquid (C1) was obtained as described above. 4.15 parts by mass of sodium chloride was added to 20.40 parts by mass of the obtained thickener-containing liquid (C1), and dissolved by stirring and mixing to obtain 24.55 parts by mass of thickener-containing liquid (C2).

[0122] <Preparation of Pre-mixture (D1)> 44.06 parts by mass of the pesticidal active compound emulsion (A1), 21.97 parts by mass of the pesticidal active compound suspension (B1), 20.40 parts by mass of the thickener-containing liquid (C1), and 0.067 parts by mass of XIAMETER ACP-1500 were stirred and mixed to obtain 86.50 parts by mass of a pre-mixture (D1).

[0123] <Preparation of Pre-mixture (D2)> 44.06 parts by mass of the pesticidal active compound emulsion (A1), 21.97 parts by mass of the pesticidal active compound suspension (B1), 24.55 parts by mass of the thickener-containing liquid (C2), and 0.067 parts by mass of XIAMETER ACP-1500 were stirred and mixed to obtain 90.65 parts by mass of a pre-mixture (D2).

[0124] <Preparation of Pre-mixture (D3)> 33.10 parts by mass of the pesticidal active compound emulsion (A2), 21.97 parts by mass of the pesticidal active compound suspension (B1), 20.40 parts by mass of the thickener-containing liquid (C1), and 0.067 parts by mass of XIAMETER ACP-1500 were stirred and mixed to obtain 75.54 parts by mass of a pre-mixture (D3).

[0125] <Preparation of Pre-mixture (D4)> 37.21 parts by mass of an aqueous Dicamba DGA solution (dicamba acid concentration: 39.5% by mass), 21.97 parts by mass of the suspension of the pesticide active compound (B2), 20.40 parts by mass of the thickener-containing liquid (C1), and 0.13 parts by mass of XIAMETER ACP-1500 were stirred and mixed to obtain 79.71 parts by mass of a pre-mixture (D4).

[0126] <Preparation of Pre-mixture (D5)> 44.06 parts by mass of the pesticidal active compound emulsion (A1), 20.40 parts by mass of the thickener-containing liquid (C1), and 0.13 parts by mass of XIAMETER ACP-1500 were stirred and mixed to obtain 64.53 parts by mass of a pre-mixture (D5).

[0127] <Preparation of Pre-mixture (D6)> 37.21 parts by mass of an aqueous Dicamba DGA solution (dicamba acid concentration: 39.5% by mass), 21.97 parts by mass of a suspension of an agriculturally active compound (B1), 20.40 parts by mass of a thickener-containing liquid (C1), and 0.13 parts by mass of XIAMETER ACP-1500 were stirred and mixed to obtain 79.71 parts by mass of a pre-mixture (D6).

[0128] <Preparation of Pre-mixture (D7)> 46.95 parts by mass of the pesticidal active compound emulsion (A3), 21.97 parts by mass of the pesticidal active compound suspension (B1), 20.40 parts by mass of the thickener-containing liquid (C1), and 0.067 parts by mass of XIAMETER ACP-1500 were stirred and mixed to obtain 89.39 parts by mass of a pre-mixture (D7).

[0129] Comparative Production Example 1 A solution obtained by mixing 9.26 parts by mass of ion-exchanged water, 3.00 parts by mass of acetic acid, and 1.24 parts by mass of potassium hydroxide was added to 86.50 parts by mass of the premixture (D1), and the mixture was stirred and mixed to obtain a comparative pesticide composition (Y1).

[0130] Comparative Production Example 2 A solution obtained by mixing 8.75 parts by mass of ion-exchanged water, 3.69 parts by mass of propionic acid, and 1.06 parts by mass of potassium hydroxide was added to 86.50 parts by mass of the premixture (D1), and the mixture was stirred and mixed to obtain a comparative pesticide composition (Y2).

[0131] <Production Example 1> A solution obtained by mixing 8.67 parts by mass of ion-exchanged water, 3.59 parts by mass of polyacrylic acid 5,000, and 1.24 parts by mass of potassium hydroxide was added to 86.50 parts by mass of the premixture (D1), and the mixture was stirred and mixed to obtain the present pesticide composition (X1).

[0132] <Production Example 2> A solution obtained by mixing 4.00 parts by mass of ion-exchanged water, 3.59 parts by mass of polyacrylic acid 5,000, and 1.76 parts by mass of potassium hydroxide was added to 90.65 parts by mass of the premixture (D2), and the mixture was stirred and mixed to obtain the present pesticide composition (X2).

[0133] <Production Example 3> A solution obtained by mixing 7.92 parts by mass of ion-exchanged water, 3.38 parts by mass of AQUALIC TL-37, and 2.20 parts by mass of polyacrylic acid 5,000 was added to 86.50 parts by mass of the pre-mixture (D1), and the mixture was stirred and mixed to obtain the present pesticide composition (X3).

[0134] <Production Example 4> A solution obtained by mixing 8.67 parts by mass of ion-exchanged water, 3.59 parts by mass of polyacrylic acid 25,000, and 1.24 parts by mass of potassium hydroxide was added to 86.50 parts by mass of the premixture (D1), and the mixture was stirred and mixed to obtain the present pesticide composition (X4).

[0135] <Production Example 5> A solution obtained by mixing 8.83 parts by mass of ion-exchanged water, 3.59 parts by mass of polyacrylic acid 5,000, and 1.08 parts by mass of sodium hydroxide was added to 86.50 parts by mass of the premixture (D1), and the mixture was stirred and mixed to obtain the present pesticide composition (X5).

[0136] Comparative Production Example 3 A solution obtained by mixing 11.43 parts by mass of ion-exchanged water, 7.99 parts by mass of acetic acid, and 5.04 parts by mass of potassium hydroxide was added to 75.54 parts by mass of the pre-mixture (D3), and the mixture was stirred and mixed to obtain a comparative pesticide composition (Y3).

[0137] <Production Example 6> A solution obtained by mixing 9.85 parts by mass of ion-exchanged water, 9.57 parts by mass of polyacrylic acid 5,000, and 5.04 parts by mass of potassium hydroxide was added to 75.54 parts by mass of the premixture (D3), and the mixture was stirred and mixed to obtain the present pesticide composition (X6).

[0138] Comparative Production Example 4 A solution obtained by mixing 16.05 parts by mass of ion-exchanged water, 3.00 parts by mass of acetic acid, and 1.24 parts by mass of potassium hydroxide was added to 79.71 parts by mass of the pre-mixture (D4), and the mixture was stirred and mixed to obtain a comparative pesticide composition (Y4).

[0139] <Production Example 7> A solution obtained by mixing 15.46 parts by mass of ion-exchanged water, 3.59 parts by mass of polyacrylic acid 5,000, and 1.24 parts by mass of potassium hydroxide was added to 79.71 parts by mass of the premixture (D4), and the mixture was stirred and mixed to obtain the present pesticide composition (X7).

[0140] Comparative Production Example 5 A solution obtained by mixing 31.23 parts by mass of ion-exchanged water, 3.00 parts by mass of acetic acid, and 1.24 parts by mass of potassium hydroxide was added to 64.53 parts by mass of the pre-mixture (D5), and the mixture was stirred and mixed to obtain a comparative pesticide composition (Y5).

[0141] <Production Example 8> A solution obtained by mixing 30.64 parts by mass of ion-exchanged water, 3.59 parts by mass of polyacrylic acid 5,000, and 1.24 parts by mass of potassium hydroxide was added to 64.53 parts by mass of the premixture (D5), and the mixture was stirred and mixed to obtain the present pesticide composition (X8).

[0142] Comparative Production Example 6 A solution obtained by mixing 16.05 parts by mass of ion-exchanged water, 3.00 parts by mass of acetic acid, and 1.24 parts by mass of potassium hydroxide was added to 79.71 parts by mass of the pre-mixture (D6), and the mixture was stirred and mixed to obtain a comparative pesticide composition (Y6).

[0143] <Production Example 9> A solution obtained by mixing 15.46 parts by mass of ion-exchanged water, 3.59 parts by mass of polyacrylic acid 5,000, and 1.24 parts by mass of potassium hydroxide was added to 79.71 parts by mass of the premixture (D6), and the mixture was stirred and mixed to obtain the present pesticide composition (X9).

[0144] Comparative Production Example 7 A solution obtained by mixing 5.85 parts by mass of ion-exchanged water, 3.00 parts by mass of acetic acid, and 1.76 parts by mass of potassium hydroxide was added to 89.39 parts by mass of the premixture (D7), and the mixture was stirred and mixed to obtain the present pesticide composition (Y7).

[0145] <Production Example 10> A solution obtained by mixing 5.26 parts by mass of ion-exchanged water, 3.59 parts by mass of polyacrylic acid 5,000, and 1.76 parts by mass of potassium hydroxide was added to 89.39 parts by mass of the pre-mixture (D7), and the mixture was stirred and mixed to obtain the present pesticide composition (X10).

[0146] The compositions of the present pesticide compositions (X1) to (X10) and comparative pesticide compositions (Y1) to (Y7) are shown in Tables 1 and 2. The content of each component shown in Tables 1 and 2 is expressed in mass%.

[0147] Test Example 1: Evaluation of the residual rate of compound (I) The present pesticide compositions (X1) to (X10) and comparative pesticide compositions (Y1) to (Y7) were each placed in a screw tube and allowed to stand in an incubator at 54°C for 14 days. Thereafter, the content of compound (I) contained in each pesticide composition after storage was analyzed by HPLC, and the residual rate of compound (I) was evaluated using the following calculation formula. The results are shown in Tables 1 and 2. The higher the residual rate of compound (I), the higher the effect of inhibiting the decomposition of compound (I). Residual rate of compound (I) [%] = 100 x A / B A: Content of compound (I) in each pesticide composition after storage at 54°C for 14 days B: Content of compound (I) in each pesticide composition immediately after preparation

[0148] Test Example 2: Identification of decomposition products of compound (I) A mass spectrum was measured for a composition containing compound (IA), compound (IB), dicamba diglycolamine salt, acetic acid, and potassium hydroxide, which had been left for 8 weeks in an incubator at 50° C. As a result, decomposition products a and b, which are represented by the following formulas and are decomposition products of compound (IA), and decomposition product c, which is represented by the following formula and is a decomposition product of compound (IB), were identified.

[0149]

[0150] Decomposition product a is generated as a result of the cleavage of the C-N bond (the bond between the N atom at position 3 and the C atom at position 4) contained in the imide structure constituting the uracil ring structure of compound (IA) and the bond between the N atom at position 1 and the C atom at position 6, resulting in the opening of the uracil ring. Decomposition product b is generated as a result of the opening of the uracil ring of compound (IA) and the addition of DGA (diglycolamine) to the terminal ethyl ester moiety. Decomposition product c is generated as a result of the cleavage of two C-N bonds contained in the imide structure of compound (IB).

[0151] From the results of Test Example 2, it can be seen that the technology of the present invention is effective in inhibiting the decomposition of compounds having an amide structure, a uracil ring structure or an imide structure containing an amide structure, or an ester structure.

[0152] Test Example 3: Evaluation of dicamba volatilization amount (1) Preparation of measurement samples For each of the present pesticide compositions (X1) to (X10) and the comparative pesticide compositions (Y1) to (Y7), 8.16 parts by mass of the pesticide composition was mixed with 6.03 parts by mass of Roundup PowerMAX (registered trademark, a product of Bayer CropScience containing 48.7% by mass of glyphosate potassium salt) and 85.81 parts by mass of ion-exchanged water to prepare 100 parts by mass of a diluted solution of the pesticide composition, which was used as a measurement sample. Furthermore, 3.01 parts by mass of Clarity (registered trademark, a product of BASF containing 58.1% by mass of dicamba diglycolamine salt), 6.03 parts by mass of Roundup PowerMAX, and 90.96 parts by mass of ion-exchanged water were mixed to prepare 100 parts by mass of a control.

[0153] (2) Evaluation of the Volatilization Amount of Dicamba This will be explained with reference to FIG. 1, a cross-sectional schematic diagram showing the evaluation apparatus. A 6.5 cm diameter glass Petri dish 200 containing the entire amount of measurement sample 100 prepared in (1) above was placed on a temperature-regulating mat 300 (round Samicon 230 heater, manufactured by Sakaguchi Electric Heating Co., Ltd.). A dome-shaped glass cover 400 was placed on top of it. This cover 400 had an opening at the top and multiple notches 450 at regular intervals at the bottom for introducing outside air. A connecting pipe 500 was connected to the opening at the top of the cover 400, and the connecting pipe 500 and a suction pump 600 were connected by a tube. At this time, a flow meter 650 was placed between the connecting pipe 500 and the suction pump 600. In addition, polyurethane foam 550 (manufactured by SKC Inc., diameter 22 mm, length 76 mm) was placed inside the connecting pipe 500.

[0154] With the temperature-regulating mat 300 controlled at 35°C, the suction pump 600 was started, drawing in outside air through the notch 450 and generating a gas flow toward the suction pump 600. The gas suction rate was 2 L / min. The suction pump 600 was operated for 24 hours. Thereafter, the polyurethane foam 550 was recovered, and the dicamba absorbed in the polyurethane foam 550 was extracted using methanol and quantitatively analyzed using LC-MS. The amount of dicamba extracted, determined from the quantitative analysis, corresponds to the amount of dicamba volatilized. The same test as above was also conducted on the control.

[0155] The relative amount of dicamba volatilized in each diluted solution of the pesticide composition was calculated, assuming the amount of dicamba volatilized in the control to be 1. The results are shown in Tables 1 and 2.

[0156] Test Example 4: Measurement of pH of pesticide compositions The pH value at 25°C was measured for each of the present pesticide compositions (X1) to (X10) and comparative pesticide compositions (Y1) to (Y7) according to the following procedure. The pesticide compositions were placed in glass containers and shaken by hand. Next, the electrodes of a pH meter ("Desktop pH Meter F-71S" manufactured by HORIBA) were immersed in the pesticide compositions to measure the pH values. The results are shown in Tables 1 and 2.

[0157]

[0158]

[0159] Test Example 5: Pesticide compositions (Z1) to (Z5) having the compositions shown in Table 3 were prepared according to the methods for preparing the pesticide compositions (X1) to (X10) and comparative pesticide compositions (Y1) to (Y7) described above. The units of the content of each component shown in Table 3 are % by mass. For each of the pesticide compositions (Z1) to (Z5), the residual rate of compound (I) and the amount of volatilization of 2,4-D were evaluated according to the same methods as in Test Examples [1] and [3] described above. As a result, it was confirmed that all of the pesticide compositions (Z1) to (Z5) are pesticide compositions that can inhibit the volatilization of 2,4-D and the decomposition of compound (I).

[0160]

[0161] 100 Measurement sample, 200 Glass Petri dish, 300 Temperature control mat, 400 Cover, 450 Notch, 500 Connecting tube, 550 Polyurethane foam, 600 Suction pump, 650 Flow meter.

Claims

1. A dicamba amine salt; The following formula (I): -C(=O)-X- (I) [wherein X represents an oxygen atom and NR 1 and R represents at least one selected from the group consisting of 1 represents a monovalent group. and a pesticidal active compound having a partial structure represented by the formula: and at least one member selected from the group consisting of polycarboxylic acids and salts thereof.

2. The pesticidal active compound has the following formula (I-1): wherein X has the same meaning as defined above. R 2 represents a monovalent group. R 3 represents a monovalent group when X is an oxygen atom, and 1 When C(=O)-R 4 Represents. R 4 represents a monovalent group, and R 2 and R 4 And, R 2 the carbon atoms bonded to X and R 4 may form a ring together with the carbon atom bonded to The liquid pesticide composition according to claim 1, wherein the compound is represented by the formula:

3. 2. The liquid pesticide composition according to claim 1, wherein the polycarboxylic acid comprises at least one polycarboxylic acid selected from the group consisting of a copolymer of acrylic acid and maleic acid and polyacrylic acid.

4. 2. The liquid pesticide composition according to claim 1, wherein the dicamba amine salt comprises at least one dicamba amine salt selected from the group consisting of dicamba diglycolamine salts and dicamba monoethanolamine salts.

5. The liquid pesticide composition according to claim 1, further comprising a basic component.

6. The liquid pesticide composition according to claim 1, further comprising an alkali metal hydroxide.

7. 2. The liquid pesticide composition according to claim 1, further comprising at least one alkali metal hydroxide selected from the group consisting of potassium hydroxide and sodium hydroxide.

8. The liquid pesticide composition according to claim 5, wherein the concentration of the basic component is 0.0001 mol / L or more and 0.050 mol / L or less.

9. 2. The liquid pesticide composition according to claim 1, wherein the pesticidal active compound comprises a PPO inhibitor.

10. A liquid pesticide composition according to claim 1, wherein the pH value of the liquid pesticide composition at 25°C is 4.8 or more and 6.5 or less.

Images