JP7305232B1 - Crystal growth inhibitor and agricultural chemical composition containing the same - Google Patents
Crystal growth inhibitor and agricultural chemical composition containing the same Download PDFInfo
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- JP7305232B1 JP7305232B1 JP2022199151A JP2022199151A JP7305232B1 JP 7305232 B1 JP7305232 B1 JP 7305232B1 JP 2022199151 A JP2022199151 A JP 2022199151A JP 2022199151 A JP2022199151 A JP 2022199151A JP 7305232 B1 JP7305232 B1 JP 7305232B1
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- crystal growth
- agricultural chemical
- growth inhibitor
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- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
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- 235000010296 thiabendazole Nutrition 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
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- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
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Abstract
【課題】懸濁剤中の粒子の成長を抑制できる結晶成長抑制剤と、それを用いた農薬組成物を提供する。【解決手段】結晶成長抑制剤を、特定構造の化合物由来の構成単位（Ｓ１）とアクリル酸メチル又はメタクリル酸メチル由来の構成単位（Ｓ２）とを含む共重合体を含有するものとする。共重合体は、分子量１５０以下の不飽和カルボン酸またはその無水物由来の構成単位（Ｓ３）を更に含むことが好ましい。農薬組成物は、農薬活性成分と結晶成長抑制剤とを含有する。【選択図】なしA crystal growth inhibitor capable of suppressing the growth of particles in a suspension and an agricultural chemical composition using the same are provided. A crystal growth inhibitor contains a copolymer containing a structural unit (S1) derived from a compound having a specific structure and a structural unit (S2) derived from methyl acrylate or methyl methacrylate. The copolymer preferably further contains a structural unit (S3) derived from an unsaturated carboxylic acid having a molecular weight of 150 or less or its anhydride. The agricultural chemical composition contains an agricultural chemical active ingredient and a crystal growth inhibitor. [Selection figure] None
Description
本開示は、結晶成長抑制剤、及びそれを含有する農薬組成物に関する。 FIELD OF THE DISCLOSURE The present disclosure relates to crystal growth inhibitors and agricultural chemical compositions containing the same.
農業には多種多様な農薬が使用されており、その性状により複数の剤型に分類される。剤型としては、粉剤、粒剤、水和剤、顆粒水和剤（ドライフロアブル）、懸濁剤（フロアブル剤）、乳剤、ＥＷ剤（エマルション）、マイクロカプセル剤、燻煙剤等が挙げられる。 A wide variety of agricultural chemicals are used in agriculture, and are classified into a plurality of dosage forms according to their properties. Dosage forms include powders, granules, wettable powders, wettable granules (dry flowables), suspensions (flowables), emulsions, EW agents (emulsions), microcapsules, smoking agents, and the like. .
上記剤型の中でも懸濁剤は、水に対して不溶又は溶解度が小さい農薬活性成分を微小粒子の状態に粉砕し、分散剤や界面活性剤を添加して水に分散させた製剤である。このように本来水に溶解しない又は溶解しにくい農薬活性成分を粒子状で水中に均一に懸濁させることにより、農薬活性成分の散布が容易になる。また、懸濁剤は有機溶剤を含まないため、作業者が気化した有機溶剤を吸入する危険性がない。 Among the above formulations, suspensions are formulations prepared by pulverizing pesticidal active ingredients, which are insoluble or less soluble in water, into microparticles and dispersing them in water with the addition of dispersants and surfactants. By uniformly suspending the pesticidally active ingredient in the form of particles in water, the pesticidally active ingredient can be easily sprayed. Also, since the suspension does not contain an organic solvent, there is no risk of the worker inhaling the vaporized organic solvent.
従来、特許文献１～５に開示の懸濁剤が知られている。特許文献１は、エマルションとして製剤された活性成分、及び、分子量が少なくとも２５０であり水性媒体によって溶媒和され得る成分と分子量が少なくとも５００であり最小の疎水性度を有する成分との共重合体である分散剤を含有する組成物を開示している。特許文献２は、活性物質、アクリルグラフトポリマー群からの非イオン性ポリマーに基づく界面活性剤、及び、キサンタンガム群からのアニオン性ヘテロ多糖類に基づく増粘剤を必須成分とする組成物を開示している。特許文献３は、活性成分、及び、アクリル酸と、疎水性モノマーと、モノアルキルポリエチレングリコールのアルキルアクリレートとのポリマーを含むポリマー分散剤を含有する組成物を開示している。特許文献４は、疎水性非重合体固体微粒子、及び、分子量が少なくとも２５０である水性媒体によって溶媒和される成分と分子量が少なくとも５００であり最小の疎水性度を有する成分との共重合体である分散剤を含有する組成物を開示している。特許文献５は、水性媒体に不溶性の粒子及び両親媒性安定剤を含有する組成物であって、両親媒性安定剤は、分子量が少なくとも１０，０００でありα、β－エチレン性不飽和単量体の共重合体からなる骨格構造と、分子量が少なくとも３５０であり水性媒体によって溶媒和される側鎖状の非イオン性構造を少なくとも２つ有する組成物を開示する。 Conventionally, suspending agents disclosed in Patent Documents 1 to 5 are known. WO 2005/010002 discloses an active ingredient formulated as an emulsion and a copolymer of a component having a molecular weight of at least 250 and capable of being solvated by an aqueous medium and a component having a molecular weight of at least 500 and having minimal hydrophobicity. Compositions containing certain dispersants are disclosed. US Pat. No. 5,330,002 discloses compositions essentially comprising an active substance, a surfactant based on a nonionic polymer from the group of acrylic grafted polymers, and a thickener based on an anionic heteropolysaccharide from the group of xanthan gum. ing. US Pat. No. 5,300,002 discloses compositions containing an active ingredient and a polymeric dispersant comprising polymers of acrylic acid, hydrophobic monomers and alkyl acrylates of monoalkyl polyethylene glycols. US Pat. No. 5,301,003 describes hydrophobic non-polymeric solid particulates and copolymers of components solvated by an aqueous medium having a molecular weight of at least 250 and components having a molecular weight of at least 500 and having minimal hydrophobicity. Compositions containing certain dispersants are disclosed. US Pat. No. 5,300,005 discloses a composition containing particles insoluble in an aqueous medium and an amphiphilic stabilizer, wherein the amphiphilic stabilizer has a molecular weight of at least 10,000 and is an α,β-ethylenically unsaturated monomer. Disclosed are compositions having a backbone structure consisting of a copolymer of monomers and at least two pendant nonionic structures having a molecular weight of at least 350 and which are solvated by an aqueous medium.
しかし、懸濁剤は長期保存すると農薬活性成分の粒子が成長（例えば、凝集、結晶成長、又はオストワルド熟成）し、粒子径が大きくなる。その場合、粒子の沈降による成分の分離・不均一化、散布時における噴霧器のノズルの目詰まり、対象生物の取込効率の低下などが生じる可能性がある。特に、懸濁剤に用いられる農薬活性成分の中でも比較的溶解度が高い、例えば１００ｐｐｍ以上の農薬活性成分は粒子の凝集や結晶成長が起こりやすい。そのため、本開示は懸濁剤中の粒子の成長を抑制できる結晶成長抑制剤を提供することを課題とする。また、それを用いた農薬組成物も提供する。 However, when the suspending agent is stored for a long period of time, the particles of the pesticidal active ingredient grow (for example, aggregation, crystal growth, or Ostwald ripening) and the particle size increases. In this case, sedimentation of particles may lead to separation and non-uniformity of components, clogging of sprayer nozzles during spraying, and reduction in efficiency of capturing target organisms. In particular, among agriculturally active ingredients used in suspensions, those having relatively high solubility, for example, 100 ppm or more, tend to cause aggregation of particles and crystal growth. Therefore, an object of the present disclosure is to provide a crystal growth inhibitor capable of suppressing the growth of particles in a suspension. Also provided is an agrochemical composition using the same.
そのための手段として、本開示は以下の手段を採る。
［１］下記式１で示される化合物由来の構成単位（Ｓ１）と下記式２で示される化合物由来の構成単位（Ｓ２）と分子量１５０以下の不飽和カルボン酸またはその無水物由来の構成単位（Ｓ３）のみからなる共重合体を含有し、前記構成単位（Ｓ１）、前記構成単位（Ｓ２）、及び前記構成単位（Ｓ３）の合計を１００重量％とした場合に、前記構成単位（Ｓ１）が４９～８０重量％であり、前記構成単位（Ｓ２）が１９～５０重量％であり、前記構成単位（Ｓ３）が１～１５重量％であり、前記構成単位（Ｓ１）、前記構成単位（Ｓ２）、及び前記構成単位（Ｓ３）はランダム共重合されていることを特徴とする結晶成長抑制剤。
（式中、Ｒ１は水素原子又はメチル基であり、Ｒ２Ｏは炭素数２～３のオキシアルキレン基であり、ｎは２３～１１４の整数であり、Ｒ３は炭素数１～８の炭化水素基である。）
（式中、Ｒ４は水素原子又はメチル基である。）
［２］前記ｎは４５～１１４の整数である、［１］の結晶成長抑制剤。
［３］前記共重合体の数平均分子量が２，０００～１００，０００である、［１］の結晶成長抑制剤。
［４］農薬活性成分と、［１］から［３］のいずれかの結晶成長抑制剤とを含有することを特徴とする農薬組成物。
［５］水を更に含有し、
前記農薬活性成分、前記結晶成長抑制剤、及び前記水の合計を１００重量％とした場合に、前記農薬活性成分が０．５～５０重量％であり、前記結晶成長抑制剤が０．１～１０重量％であり、前記水が４０～９９重量％である、［４］の農薬組成物。
［６］農薬活性成分と、結晶成長抑制剤とを含有する農薬組成物であって、前記結晶成長抑制剤は、下記式１で示される化合物由来の構成単位（Ｓ１）と下記式２で示される化合物由来の構成単位（Ｓ２）と分子量１５０以下の不飽和カルボン酸またはその無水物由来の構成単位（Ｓ３）のみからなる共重合体であり、前記共重合体の数平均分子量が２，０００～１００，０００であることを特徴とする農薬組成物。
（式中、Ｒ
１
は水素原子又はメチル基であり、Ｒ
２
Ｏは炭素数２～３のオキシアルキレン基であり、ｎは２３～１１４の整数であり、Ｒ
３
は炭素数１～８の炭化水素基である。）
（式中、Ｒ
４
は水素原子又はメチル基である。）
［７］前記構成単位（Ｓ１）、前記構成単位（Ｓ２）、及び前記構成単位（Ｓ３）の合計を１００重量％とした場合に、前記構成単位（Ｓ１）が４９～８０重量％であり、前記構成単位（Ｓ２）が１９～５０重量％であり、前記構成単位（Ｓ３）が１～１５重量％である、［６］の農薬組成物。
［８］前記ｎは４５～１１４の整数である、［６］の農薬組成物。
［９］水を更に含有し、前記農薬活性成分、前記結晶成長抑制剤、及び前記水の合計を１００重量％とした場合に、前記農薬活性成分が０．５～５０重量％であり、前記結晶成長抑制剤が０．１～１０重量％であり、前記水が４０～９９重量％である、［６］から［８］のいずれかの農薬組成物。
As means for that purpose, the present disclosure employs the following means.
[1] A structural unit (S1) derived from a compound represented by the following formula 1, a structural unit (S2) derived from a compound represented by the following formula 2, and a structural unit derived from an unsaturated carboxylic acid having a molecular weight of 150 or less or an anhydride thereof ( S3) containing a copolymer consisting only of the structural unit (S1) when the total of the structural unit (S1), the structural unit (S2), and the structural unit (S3) is 100% by weight. is 49 to 80% by weight, the structural unit (S2) is 19 to 50% by weight, the structural unit (S3) is 1 to 15% by weight, the structural unit (S1), the structural unit ( S2) and the structural unit (S3) are randomly copolymerized .
(wherein R 1 is a hydrogen atom or a methyl group, R 2 O is an oxyalkylene group having 2 to 3 carbon atoms, n is an integer of 23 to 114, and R 3 is a It is a hydrocarbon group.)
(Wherein, R4 is a hydrogen atom or a methyl group.)
[2] The crystal growth inhibitor of [1], wherein n is an integer of 45-114.
[ 3 ] The crystal growth inhibitor of [1], wherein the copolymer has a number average molecular weight of 2,000 to 100,000.
[ 4 ] An agricultural chemical composition comprising an agricultural chemical active ingredient and the crystal growth inhibitor according to any one of [1] to [ 3 ].
[ 5 ] further containing water,
When the sum of the agricultural chemical active ingredient, the crystal growth inhibitor, and the water is 100% by weight, the agricultural chemical active ingredient is 0.5 to 50% by weight, and the crystal growth inhibitor is 0.1 to 50% by weight. 10% by weight, and the water is 40-99% by weight, the agricultural chemical composition of [ 4 ].
[6] An agricultural chemical composition containing an agricultural chemical active ingredient and a crystal growth inhibitor, wherein the crystal growth inhibitor is a structural unit (S1) derived from a compound represented by the following formula 1 and represented by the following formula 2: and a structural unit (S3) derived from an unsaturated carboxylic acid having a molecular weight of 150 or less or an anhydride thereof, and the number average molecular weight of the copolymer is 2,000. -100,000.
(wherein R 1 is a hydrogen atom or a methyl group, R 2 O is an oxyalkylene group having 2 to 3 carbon atoms, n is an integer of 23 to 114, and R 3 is a It is a hydrocarbon group.)
(Wherein, R4 is a hydrogen atom or a methyl group.)
[7] When the total of the structural unit (S1), the structural unit (S2), and the structural unit (S3) is 100% by weight, the structural unit (S1) is 49 to 80% by weight, The agricultural chemical composition of [6], wherein the structural unit (S2) is 19 to 50% by weight and the structural unit (S3) is 1 to 15% by weight.
[8] The agricultural chemical composition of [6], wherein n is an integer of 45-114.
[9] Water is further contained, and when the total amount of the agricultural chemical active ingredient, the crystal growth inhibitor, and the water is 100% by weight, the agricultural chemical active ingredient is 0.5 to 50% by weight, and The agricultural chemical composition according to any one of [6] to [8], wherein the crystal growth inhibitor is 0.1-10% by weight and the water is 40-99% by weight.
なお、本明細書において「Ｙ～Ｚ」で示される数値範囲は、その上限及び下限を含む範囲を意味する。つまり、「Ｙ～Ｚ」は「Ｙ以上、Ｚ以下」を意味する。 In this specification, the numerical range indicated by "Y to Z" means a range including its upper and lower limits. That is, "Y to Z" means "Y or more and Z or less".
≪結晶成長抑制剤≫
本開示の結晶成長抑制剤は、それぞれ特定構造を有する構成単位（Ｓ１）と構成単位（Ｓ２）と構成単位（Ｓ３）のみからなる共重合体を含有する。本開示の結晶成長抑制剤は、農薬組成物中において農薬活性成分の粒子がオストワルド熟成等により成長することを抑制できる。
<<Crystal growth inhibitor>>
The crystal growth inhibitor of the present disclosure contains a copolymer consisting only of a structural unit (S1), a structural unit (S2) and a structural unit (S3) each having a specific structure . The crystal growth inhibitor of the present disclosure can suppress the growth of particles of the agricultural chemical active ingredient due to Ostwald ripening or the like in the agricultural chemical composition.
＜構成単位（Ｓ１）＞
構成単位（Ｓ１）は、下記式１で示される化合物（単量体）由来の構成単位である。
（式中、Ｒ１は水素原子又はメチル基であり、Ｒ２Ｏは炭素数２～３のオキシアルキレン基であり、ｎは２３～１１４の整数であり、Ｒ３は炭素数１～８の炭化水素基である。）
式１で示される化合物としては、例えば、α－メタクリロイル－ω－メトキシ－ポリオキシエチレン（２３モル）、α－メタクリロイル－ω－メトキシ－ポリオキシプロピレン（２３モル）、α－メタクリロイル－ω－プロポキシ－ポリオキシエチレン（２３モル）、α－メタクロイル－ω－２－エチルへキシルオキシ－ポリオキシエチレン（２３モル）、α－メタクリロイル－ω－メトキシ－ポリオキシエチレン（４０モル）ポリオキシプロピレン（１５モル）（ランダム共重合体)、α－メタクリロイル－ω－メトキシ－ポリオキシエチレン（４０モル）ポリオキシプロピレン（１５モル）（ブロック共重合体）、α－アクリロイル－ω－メトキシ－ポリオキシエチレン（４５モル）、α－メタクリロイル－ω－メトキシ－ポリオキシエチレン（４５モル）、α－メタクリロイル－ω－エトキシ－ポリオキシエチレン（４５モル）、α－メタクリロイル－ω－ブトキシ－ポリオキシエチレン（４５モル）、α－メタクリロイル－ω－メトキシ－ポリオキシプロピレン（４５モル）、α－メタクリロイル－ω－メトキシ－ポリオキシエチレン（１１３モル）が挙げられる。式１で示される化合物は１種単独で用いてもよいし、２種以上を併用してもよい。なお、本明細書において、ポリオキシエチレン（１４モル）等の成分名に示す括弧内のモル数は、対応するアルキレンオキサイドの付加モル数を示す。
<Constituent unit (S1)>
The structural unit (S1) is a structural unit derived from a compound (monomer) represented by formula 1 below.
(wherein R 1 is a hydrogen atom or a methyl group, R 2 O is an oxyalkylene group having 2 to 3 carbon atoms, n is an integer of 23 to 114, and R 3 is a It is a hydrocarbon group.)
Examples of compounds represented by Formula 1 include α-methacryloyl-ω-methoxy-polyoxyethylene (23 mol), α-methacryloyl-ω-methoxy-polyoxypropylene (23 mol), α-methacryloyl-ω-propoxy - polyoxyethylene (23 mol), α-methacryloyl-ω-2-ethylhexyloxy-polyoxyethylene (23 mol), α-methacryloyl-ω-methoxy-polyoxyethylene (40 mol), polyoxypropylene (15 mol) ) (random copolymer ), α-methacryloyl-ω-methoxy-polyoxyethylene (40 mol) polyoxypropylene (15 mol) ( block copolymer), α-acryloyl-ω-methoxy-polyoxyethylene (45 mol), α-methacryloyl-ω-methoxy-polyoxyethylene (45 mol), α-methacryloyl-ω-ethoxy-polyoxyethylene (45 mol), α-methacryloyl-ω-butoxy-polyoxyethylene (45 mol) , α-methacryloyl-ω-methoxy-polyoxypropylene (45 mol), α-methacryloyl-ω-methoxy-polyoxyethylene (113 mol). The compounds represented by Formula 1 may be used singly or in combination of two or more. In this specification, the number of moles in parentheses shown in component names such as polyoxyethylene (14 mol) indicates the number of moles of the corresponding added alkylene oxide.
式１中のＲ２Ｏ、Ｒ３、及びｎは、結晶成長抑制効果の観点からそれぞれ好ましい官能基又は数値範囲がある。Ｒ２Ｏは炭素数２のオキシエチレン基が好ましい。Ｒ３はメチル基が好ましい。ｎは４５～１１４が好ましい。なお、Ｒ２Ｏがオキシエチレン基及びオキシプロピレン基である場合、両者はブロック重合されていてもよいし、ランダム重合されていてもよい。 R 2 O, R 3 and n in Formula 1 each have a preferred functional group or numerical range from the viewpoint of the effect of suppressing crystal growth. R 2 O is preferably an oxyethylene group having 2 carbon atoms. R 3 is preferably a methyl group. n is preferably 45-114. When R 2 O is an oxyethylene group and an oxypropylene group, both may be block-polymerized or random-polymerized.
＜構成単位（Ｓ２）＞
構成単位（Ｓ２）は、下記式２で示される化合物（単量体）由来の構成単位である。
（式中、Ｒ４は水素原子又はメチル基である。）
つまり、式２で示される化合物はアクリル酸メチル又はメタクリル酸メチルである。
<Constituent unit (S2)>
The structural unit (S2) is a structural unit derived from a compound (monomer) represented by formula 2 below.
(Wherein, R4 is a hydrogen atom or a methyl group.)
That is, the compound represented by Formula 2 is methyl acrylate or methyl methacrylate.
＜構成単位（Ｓ３）＞
構成単位（Ｓ３）は、分子量１５０以下の不飽和カルボン酸又はその無水物由来の構成単位である。分子量１５０以下の不飽和カルボン酸としては、例えば、アクリル酸、クロトン酸、イソクロトン酸、３－ブテン酸、メタクリル酸、４－ペンテン酸、イタコン酸、フマル酸、シトラコン酸、マレイン酸、アリルマロン酸、無水マレイン酸、シトラコン酸無水物、無水フタル酸が挙げられる。構成単位（Ｓ３）は、結晶成長抑制効果の観点から、アクリル酸及びメタクリル酸の少なくとも一方由来であることが好ましい。
<Constituent unit (S3)>
The structural unit (S3) is a structural unit derived from an unsaturated carboxylic acid having a molecular weight of 150 or less or its anhydride. Examples of unsaturated carboxylic acids having a molecular weight of 150 or less include acrylic acid, crotonic acid, isocrotonic acid, 3-butenoic acid, methacrylic acid, 4-pentenoic acid, itaconic acid, fumaric acid, citraconic acid, maleic acid, allylmalonic acid, Maleic anhydride, citraconic anhydride, phthalic anhydride can be mentioned. The structural unit (S3) is preferably derived from at least one of acrylic acid and methacrylic acid from the viewpoint of the effect of suppressing crystal growth.
≪共重合体≫
共重合体は、構成単位（Ｓ１）、構成単位（Ｓ２）及び構成単位（Ｓ３）のみからなる。共重合体の数平均分子量は、結晶成長抑制効果の観点から、２，０００～１００，０００であることが好ましい。また、共重合体の数平均分子量の下限は１０，０００以上であることが更に好ましい。一方、上限は３０，０００以下であることが更に好ましい。
≪Copolymer≫
The copolymer consists only of the structural unit (S1) , the structural unit (S2) and the structural unit (S3). The number average molecular weight of the copolymer is preferably from 2,000 to 100,000 from the viewpoint of the effect of suppressing crystal growth. Further, the lower limit of the number average molecular weight of the copolymer is more preferably 10,000 or more. On the other hand, the upper limit is more preferably 30,000 or less.
共重合体は、単量体として、上記式１で示される化合物、上記式２で示される化合物、及び分子量１５０以下の不飽和カルボン酸又はその無水物を共重合することにより得られる。重合方法は公知の方法が使用可能であり、特に限定されないが、例えば連鎖重合が挙げられる。 The copolymer is obtained by copolymerizing the compound represented by the above formula 1, the compound represented by the above formula 2, and an unsaturated carboxylic acid having a molecular weight of 150 or less or an anhydride thereof as monomers. . A known method can be used for the polymerization method, and although there is no particular limitation, for example, chain polymerization can be mentioned.
共重合体の構成単位（Ｓ１）～（Ｓ３）の合計を１００重量％とすると、構成単位（Ｓ１）が４９～８０重量％、構成単位（Ｓ２）が１９～５０重量％、構成単位（Ｓ３）が１～１５重量％であることが好ましい。なお、本明細書中において、各構成単位の重量％は共重合に用いられた各単量体の重量％を意味する。 When the total of the structural units (S1) to (S3) of the copolymer is 100% by weight, the structural unit (S1) is 49 to 80% by weight, the structural unit (S2) is 19 to 50% by weight, the structural unit (S3 ) is preferably 1 to 15% by weight. In addition, in this specification, the weight % of each structural unit means the weight % of each monomer used for copolymerization.
≪農薬組成物≫
農薬組成物は、結晶成長抑制剤と農薬活性成分とを含有する。農薬組成物は、農薬活性成分に対する分散媒、例えば水を更に含有することが好ましい。農薬活性成分としては、除草剤、殺虫剤、殺ダニ剤、殺線虫剤、抗ウイルス剤、植物成長調節剤、殺菌剤、誘引剤、忌避剤等が挙げられる。中でも、懸濁剤として使用される農薬活性成分であって、分散媒に対して高い溶解度、例えば１００ｐｐｍ以上を有する農薬活性成分が好ましい。本発明の農薬組成物に含まれる農薬活性成分は、１種のみであってもよいし、２種以上であってもよい。
≪Pesticide composition≫
The agricultural chemical composition contains a crystal growth inhibitor and an agricultural chemical active ingredient. The agricultural chemical composition preferably further contains a dispersing medium for the agricultural chemical active ingredient, such as water. Agrochemical active ingredients include herbicides, insecticides, acaricides, nematicides, antiviral agents, plant growth regulators, fungicides, attractants, repellents, and the like. Among them, an agrochemical active ingredient that is used as a suspending agent and has a high solubility in the dispersion medium, for example, 100 ppm or more, is preferable. The agricultural chemical composition of the present invention may contain only one agricultural chemical active ingredient, or two or more agricultural chemical active ingredients.
除草剤としては、アイオキシニル、アジムスルフロン、アシュラム、アトラジン、アニロホス、イソウロン、イソキサベン、イマゼタピル、イマゾスルフロン、インダノファン、エスプロカルブ、エトベンザニド、オキサジアゾン、オキサジアルギル、オキサジクロメホン、オリザリン、カフェンストロール、カルブチレート、キザロホップメチル、クミルロン、クロメプロップ、クロルフタリム、シアナジン、シクロスルファムロン、ジチオピル、シデュロン、シノスルフロン、シハロホップブチル、ジフルフェニカン、ジメタメトリン、シメトリン、ダイムロン、ダゾメット、チフェンスルフロンメチル、デスメディファム、テニルクロール、テプラロキシジム、テフリルトリオン、トリアジフラム、トリフルラリン、トルピラレート、ナプロパミド、ニコスルフロン、ハロスルフロンメチル、ビフェノックス、ピラゾキシフェン、ピラゾスルフロンメチル、ピラクロニル、ピラゾエート、ピラフルフェンエチル、ピリフタリド、ピリブチカルブ、ピリミノバックメチル、フェノチオール、フェントラザミド、フェンメディファム、フラザスルフロン、フルチアセットメチル、フルミオキサジン、プロジアミン、プロピサミド、ブロマシル、プロメトリン、ブロモブチド、フロラスラム、ベスロジン、ベンスルフロンメチル、ベンゾフェナップ、ベンゾビシクロン、ペンディメタリン、ペントキサゾン、メタミトロン、メトスルフロンメチル、メトリブジン、メフェナセット、リニュロン、リムスルフロン、レナシル、ＡＣＮ、シマジン、ジクロベニル、クロルチアミド、ジウロン、プロパニル等が挙げられる。 Herbicides include ioxynil, azimsulfuron, ashram, atrazine, anilophos, isouron, isoxaben, imazethapyr, imazosulfuron, indanophan, esprocarb, etobenzanide, oxadiazon, oxadiargyl, oxadiclomefon, oryzarin, caffenstrol, carbyrate, quizalofop-methyl, cumyluron, and clomeprop. , chlorphthalim, cyanazine, cyclosulfamuron, dithiopyr, siduron, cinosulfuron, cyhalofop-butyl, diflufenican, dimethamethrin, simetryn, daimuron, dazomet, thifensulfuron-methyl, desmedifam, thenylchlor, tepraloxydim, tefuryltrione, triazifuram, trifluralin, tolpiralate, napropamide, nicosulfuron, halosulfuron-methyl, bifenox, pyrazoxifene, pyrazosulfuron-methyl, pyraclonil, pyrazoate, pyraflufen-ethyl, pyriftalide, piributicarb, pyriminobac-methyl, phenothiol, fentrazamide, fenmedi fam, flazasulfuron, fluthiacet-methyl, flumioxazin, prodiamine, propisamide, bromacil, promethrin, bromobutide, florasulam, bethrodin, bensulfuron-methyl, benzofenap, benzobiciron, pendimethalin, pentoxazone, metamitrone, metsulfuron methyl, metribuzine, mefenacet, linuron, rimsulfuron, renacil, ACN, simazine, dichlobenil, chlorthiamid, diuron, propanyl and the like.
殺虫剤としては、アバメクチン、アシノナピル、アクリナトリン、アセキノシル、アセタミプリド、アフィドピロペン、アミトラズ、アラニカルブ、イミダクロプリド、インドキサカルブ、エスフェンバレレート、エチプロール、エトキサゾール、エマメクチン安息香酸塩、塩酸レバミゾール、クロチアニジン、クロフェンテジン、クロマフェノジド、クロラントラニリプロール、クロルフェナピル、クロルフルアズロン、シアントラニリプロール、シクロプロトリン、スピノサド、スピロテトラマト、ダイアジノン、チアクロプリド、チアメトキサム、チオジカルブ、テブフェノジド、テブフェンピラド、テフルベンズロン、トラロメトリン、トルフェンピラド、ノバルロン、ビフェナゼート、ビフェントリン、ピメトロジン、ピリダベン、ピリダリル、ピリミジフェン、フィプロニル、フェニソブロモエート、フルアクリピリム、フルフェノクスロン、フロニカミド、ブロフラニリド、ヘキシチアゾクス、ベンスルタップ、ボーベリア・バシアーナ、ボーベリア・ブロンニアティ、メスルフェンホス、メトキシフェノジド、ルフェヌロン、ＢＴ（バチルス・チューリンゲンシス菌）、イソプロカルブ等が挙げられる。 Insecticides include abamectin, acinonapyr, acrinathrin, acequinosyl, acetamiprid, aphidopyropene, amitraz, alanicarb, imidacloprid, indoxacarb, esfenvalerate, ethiprole, etoxazole, emamectin benzoate, levamisole hydrochloride, clothianidin, clofentedine, and chromafenozide. , chlorantraniliprole, chlorfenapyr, chlorfluazuron, cyantraniliprole, cycloprothrin, spinosad, spirotetramat, diazinon, thiacloprid, thiamethoxam, thiodicarb, tebufenozide, tebufenpyrad, teflubenzuron, tralomethrin, tolfenpyrad, novaluron, bifenazate , bifenthrin, pymetrozine, pyridaben, pyridalyl, pyrimidifen, fipronil, phenisobromoate, fluacrypyrim, flufenoxuron, flonicamid, brofuranilide, hexythiazox, bensultap, Beauveria baciana, Beauveria brongniati, mesulfenphos, methoxyfenozide, lufenuron, BT (Bacillus thuringiensis), isoprocarb and the like.
殺菌剤としては、アシベンゾランＳメチル、アゾキシストロビン、硫黄、イソプロチオラン、イプコナゾール、イプロジオン、イミノクタジンアルベシル酸塩、イミベンコナゾール、エポキシコナゾール、オキスポコナゾールフマル酸塩、オキソリニック酸、カスガマイシン、カルプロパミド、キノメチオナート、キャプタン、クレソキシムメチル、クロロネブ、シアゾファミド、ジエトフェンカルブ、ジクロシメット、ジクロメジン、ジチアノン、ジネブ、ジフェノコナゾール、シフルフェナミド、ジフルメトリム、シプロコナゾール、シプロジニル、シメコナゾール、ジメトモルフ、シモキサニル、シュードモナス・フルオレッセンス、シュードモナスＣＡＢ－０２、ジラム、水和硫黄、チアジアジン、チアジニル、チアベンダゾール、チウラム、チオファネートメチル、チフルザミド、テクロフタラム、テトラコナゾール、テブコナゾール、トリアジメホン、トリアジン、トリコデルマ・アトロビリデ、トリシクラゾール、トリフルミゾール、トリフロキシストロビン、トリホリン、トルクルホスメチル、バチルスズブチリス、ビテルタノール、ピラクロストロビン、ピラゾホス、ピリオフェノン、ピリメタニル、ピロキロン、ファモキサドン、フェナリモル、フェノキサニル、フェリムゾン、フェンブコナゾール、フェンヘキサミド、フサライド、フラメトピル、フルアジナム、フルオルイミド、フルジオキソニル、フルスルファミド、フルトラニル、プロシミドン、プロピネブ、プロベナゾール、ヘキサコナゾール、ベノミル、ペンシクロン、ボスカリド、ポリカーバメート、マンゼブ、マンネブ、ミクロブタニル、メタスルホカルブ、メトミノストロビン、メパニピリム、有機銅、硫酸亜鉛、硫酸銅、クロロタロニル等が挙げられる。 Bactericides include acibenzolane S-methyl, azoxystrobin, sulfur, isoprothiolane, ipconazole, iprodione, iminoctadine albesilate, imibenconazole, epoxiconazole, oxpoconazole fumarate, oxolinic acid, kasugamycin, carpropamide ,,, Mushrooms, mushrooms, captan, cresoximmethyl, chloroneb, sizzo famide, dichrosimet, dicrosimet, dicromezine, dicromezin, dicromezin, diphenb, diphenoconazole, shiflephenomide, diproconazole, siproponazole, siprosnazole Metomorf, Simoxanyl, Subud Monas Fluorestence, Subu Demonas CAB -02, Giram , sulfur hydrate, thiadiazine, thiazinyl, thiabendazole, thiuram, thiophanate-methyl, thifluzamide, teclofthalam, tetraconazole, tebuconazole, triadimefon, triazine, trichoderma atroviride, tricyclazole, triflumizole, trifloxystrobin, trifoline, tolufosmethyl , bacillus subtilis, bitertanol, pyraclostrobin, pyrazophos, pyriophenone, pyrimethanil, pyroquilone, famoxadone, fenarimol, fenoxanyl, ferimzone, fenbuconazole, fenhexamide, fthalide, furametpyr, fluazinam, fluorimide, fludioxonil, fursulfamide, flutolanil, procymidone, propineb, probenazole, hexaconazole, benomyl, penciclon, boscalid, polycarbamate, mancozeb, manneb, microbutanil, metasulfocarb, metminostrobin, mepanipyrim, organic copper, zinc sulfate, copper sulfate, chlorothalonil and the like.
＜組成比＞
農薬組成物は、農薬活性成分、結晶成長抑制剤、及び水の比率は任意に設定可能であるが、農薬活性成分、結晶成長抑制剤、及び水の合計を１００重量％とした場合、農薬活性成分が０．５～５０重量％、結晶成長抑制剤が０．１～１０重量％、水が４０～９９重量％であることが好ましい。
<Composition ratio>
In the agricultural chemical composition, the ratio of the agricultural chemical active ingredient, the crystal growth inhibitor and water can be set arbitrarily. It is preferred that the component is 0.5-50% by weight, the crystal growth inhibitor is 0.1-10% by weight, and the water is 40-99% by weight.
＜添加剤＞
農薬組成物は、必要に応じて種々の添加剤を更に含有してもよい。添加剤としては、分散剤、増粘剤、凍結防止剤、消泡剤、湿潤剤などが挙げられる。
<Additive>
The agricultural chemical composition may further contain various additives as necessary. Additives include dispersants, thickeners, antifreeze agents, antifoaming agents, wetting agents, and the like.
本開示の構成及び効果を具体的な実施例及び比較例を挙げて説明する。なお、以下の説明において、重さの単位である「部」は重量部を意味する。 The configuration and effects of the present disclosure will be described with specific examples and comparative examples. In the following description, "part" as a unit of weight means part by weight.
＜実施例１－１＞
プロピレングリコール５０ｇ、構成単位Ｓ１を形成する単量体としてα－メタクリロイル－ω－メトキシ－ポリオキシエチレン（１１３モル）５３ｇ、構成単位Ｓ２を形成する単量体としてメタクリル酸メチル３５ｇ、構成単位Ｓ３を形成する単量体としてメタクリル酸１２ｇ、及び、添加剤としてドデシルメルカプタン０．５ｇを撹拌機を備えた反応容器に仕込み、雰囲気を窒素置換し撹拌しながら、徐々に加温した。反応系の温度を温水浴にて７０℃に保ち、重合開始剤として２，２’－アゾビス（２－メチルブチロニトリル）１．０ｇを一気に投入し、反応させた。その後、７０℃で３時間保持した。得られた共重合体を冷却し、イオン交換水９７ｇを加え、共重合体の４０％プロピレングリコール／水溶液である結晶成長抑制剤（Ａ－１）を得た。
<Example 1-1>
50 g of propylene glycol, 53 g of α-methacryloyl-ω-methoxy-polyoxyethylene (113 mol) as a monomer forming structural unit S1, 35 g of methyl methacrylate as a monomer forming structural unit S2, and structural unit S3. 12 g of methacrylic acid as a monomer to be formed and 0.5 g of dodecyl mercaptan as an additive were charged into a reaction vessel equipped with a stirrer, the atmosphere was replaced with nitrogen, and the mixture was gradually heated while stirring. The temperature of the reaction system was kept at 70° C. with a warm water bath, and 1.0 g of 2,2′-azobis(2-methylbutyronitrile) as a polymerization initiator was added at once to react. After that, it was held at 70° C. for 3 hours. The resulting copolymer was cooled, and 97 g of ion-exchanged water was added to obtain a crystal growth inhibitor (A-1), which was a 40% propylene glycol/water solution of the copolymer.
＜実施例１－２～１－３＞
下記表１の組成とした他は実施例１－１と同様にして、実施例１－２及び１－３の結晶成長抑制剤を作製した。
<Examples 1-2 to 1-3>
Crystal growth inhibitors of Examples 1-2 and 1-3 were produced in the same manner as in Example 1-1, except that the composition was as shown in Table 1 below.
＜実施例１－４～１－２４、比較例１－１～１－２＞
下記表１の組成とし、プロピレングリコールを７０ｇ、イオン交換水を２８ｇとした他は実施例１－１と同様にして、実施例１－４～１－２４、比較例１－１～１－２の各結晶成長抑制剤を作製した。なお、各結晶成長抑制剤は、共重合体の５０％プロピレングリコール／水溶液として得られた。
<Examples 1-4 to 1-24, Comparative Examples 1-1 to 1-2>
Examples 1-4 to 1-24 and Comparative Examples 1-1 to 1-2 were carried out in the same manner as in Example 1-1, except that the composition shown in Table 1 below was used, and 70 g of propylene glycol and 28 g of ion-exchanged water were used. Each crystal growth inhibitor was produced. Each crystal growth inhibitor was obtained as a 50% propylene glycol/water solution of the copolymer.
＜比較例１－３＞
プロピレングリコールを撹拌機を備えた反応容器に仕込み、雰囲気を窒素置換し撹拌しながら、９０℃まで加温した。反応系の温度を温水浴にて９０℃に保ち、α－メタクリロイル－ω－メトキシ－ポリオキシエチレン（１１モル）８５ｇ、スチレン７０ｇ、メタクリル酸１０５ｇ、２，２’－アゾビス（２－メチルブチロニトリル）８ｇの混合物を、２－アクリルアミド－２－メチルプロパンスルホン酸２８ｇを含む水溶液８０ｍＬと共に３．５時間かけて滴下・反応させた。その後、９０℃で２時間保持した。得られた共重合体を冷却し、水酸化ナトリウムの溶液で中和し、共重合体の３０％水溶液である結晶成長抑制剤（ａ－３）を得た。
<Comparative Example 1-3>
Propylene glycol was charged into a reaction vessel equipped with a stirrer, the atmosphere was replaced with nitrogen, and the mixture was heated to 90° C. while stirring. The temperature of the reaction system was kept at 90° C. with a warm water bath, and α-methacryloyl-ω-methoxy-polyoxyethylene (11 mol) 85 g, styrene 70 g, methacrylic acid 105 g, 2,2′-azobis(2-methylbutyro) A mixture of 8 g of nitrile) was added dropwise to react with 80 mL of an aqueous solution containing 28 g of 2-acrylamido-2-methylpropanesulfonic acid over 3.5 hours. After that, it was held at 90° C. for 2 hours. The obtained copolymer was cooled and neutralized with a sodium hydroxide solution to obtain a crystal growth inhibitor (a-3), which is a 30% aqueous solution of the copolymer.
＜比較例１－４＞
プロピレングリコール５０ｇ、α－メタクリロイル－ω－メトキシ－ポリオキシエチレン（４５モル）３７．５ｇ、メタクリル酸ラウリル６２.５ｇを撹拌機を備えた反応容器に仕込み、雰囲気を窒素置換し撹拌しながら、９０℃まで加温した。反応系の温度を温水浴にて７０℃に保ち、２，２’－アゾビス（２－メチルブチロニトリル）１．０ｇを一気に投入し反応させた。その後、７０℃で２時間保持した。得られた共重合体を冷却し、水酸化ナトリウム水溶液で中和し、イオン交換水１００ｇを加え、共重合体の４０％水溶液である結晶成長抑制剤（ａ－４）を得た。
<Comparative Example 1-4>
50 g of propylene glycol, 37.5 g of α-methacryloyl-ω-methoxy-polyoxyethylene (45 mol), and 62.5 g of lauryl methacrylate were charged into a reaction vessel equipped with a stirrer, and the atmosphere was replaced with nitrogen. It was warmed to °C. The temperature of the reaction system was kept at 70° C. with a warm water bath, and 1.0 g of 2,2′-azobis(2-methylbutyronitrile) was added at once to react. After that, it was held at 70° C. for 2 hours. The resulting copolymer was cooled, neutralized with an aqueous sodium hydroxide solution, and added with 100 g of ion-exchanged water to obtain a 40% aqueous solution of the copolymer (a crystal growth inhibitor (a-4)).
＜比較例１－５＞
下記表１の組成とした他は比較例１－４と同様にして結晶成長抑制剤（ａ－５）を作製した。
<Comparative Example 1-5>
A crystal growth inhibitor (a-5) was prepared in the same manner as in Comparative Example 1-4 except that the composition was as shown in Table 1 below.
＜比較例１－６＞
イオン交換水１６２ｇとα－メタクリロイル－ω－メトキシーポリオキシエチレン（４５モル）３２５ｇ、メタクリル酸１７５ｇ、３－メルカプトプロピオン酸６ｇを撹拌機を備えた反応容器に仕込み、雰囲気を窒素置換し撹拌しながら、徐々に加温した。反応系の温度を温水浴にて７０℃に保ち、２，２’－アゾビス（２－メチルブチロニトリル）１．０ｇを一気に投入し、反応させた。その後、７０℃で３時間保持した。得られた共重合体を冷却し、イオン交換水を加え、共重合体の５０％水溶液である結晶成長抑制剤（ａ－６）を得た。
<Comparative Example 1-6>
162 g of ion-exchanged water, 325 g of α-methacryloyl-ω-methoxy-polyoxyethylene (45 mol), 175 g of methacrylic acid, and 6 g of 3-mercaptopropionic acid were charged into a reaction vessel equipped with a stirrer, and the atmosphere was replaced with nitrogen and stirred. while gradually warming. The temperature of the reaction system was kept at 70° C. with a warm water bath, and 1.0 g of 2,2′-azobis(2-methylbutyronitrile) was added at once to react. After that, it was held at 70° C. for 3 hours. The resulting copolymer was cooled and deionized water was added to obtain a crystal growth inhibitor (a-6) which was a 50% aqueous solution of the copolymer.
＜比較例１－７＞
下記表１の組成とした他は比較例１－６と同様にして結晶成長抑制剤（ａ－７）を作製した。
A crystal growth inhibitor (a-7) was prepared in the same manner as in Comparative Example 1-6 except that the composition was as shown in Table 1 below.
表１に記載の各成分は以下の通りである。
構成単位（Ｓ１）の欄に記載の単量体
構成単位（Ｓ２）の欄に記載の単量体
Ｓ２－１：メタクリル酸メチル
Ｓ２－２：アクリル酸メチル
Ｓ２－３：スチレン
Ｓ２－４：メタクリル酸ラウリル
構成単位（Ｓ３）の欄に記載の単量体
Ｓ３－１：メタクリル酸
Ｓ３－２：アクリル酸
Ｓ３－３：無水マレイン酸
Ｓ３－４：イタコン酸
Ｓ３－５：２－アクリルアミド－２－メチルプロパンスルホン酸
添加剤
Ｃ１：ドデシルメルカプタン
Ｃ２：３－メルカプトプロピオン酸
重合開始剤（開始剤）
２，２’－アゾビス（２－メチルブチロニトリル）
Each component described in Table 1 is as follows.
The monomer described in the column of structural unit (S1)
Monomers described in the column of structural units (S2) S2-1: methyl methacrylate S2-2: methyl acrylate S2-3: styrene S2-4: lauryl methacrylate structural units (S3) Units described in the column Polymer S3-1: methacrylic acid S3-2: acrylic acid S3-3: maleic anhydride S3-4: itaconic acid S3-5: 2-acrylamido-2-methylpropanesulfonic acid additive C1: dodecyl mercaptan C2: 3 - mercaptopropionic acid polymerization initiator (initiator)
2,2'-azobis(2-methylbutyronitrile)
各結晶成長抑制剤が含有する共重合体の数平均分子量を下記方法で測定した。その結果を表１に示す。 The number average molecular weight of the copolymer contained in each crystal growth inhibitor was measured by the following method. Table 1 shows the results.
［数平均分子量の測定］
共重合物の数平均分子量の測定は、ゲルパーミエーションクロマトグラフィー法（ＧＰＣ）にて行い、以下の測定条件を用いた。
検出器：示差屈折計（ＲＩ)
カラム：昭和電工株式会社製 OHpak SB-G 6B+SB-804 HQ+SB-802.5 HQ
溶離液：５０ｍＭ 硝酸ナトリウム水溶液
流速：０.７ｍＬ／分
カラム温度：４０℃
標準物質：アジレント・テクノロジー株式会社製ポリエチレングリコール／酸化物（ＰＥＧ／ＰＥＯ）
[Measurement of number average molecular weight]
The number average molecular weight of the copolymer was measured by gel permeation chromatography (GPC) under the following measurement conditions.
Detector: differential refractometer (RI)
Column: Showa Denko OHpak SB-G 6B+SB-804 HQ+SB-802.5 HQ
Eluent: 50 mM aqueous sodium nitrate solution Flow rate: 0.7 mL/min Column temperature: 40°C
Reference material: Polyethylene glycol/oxide (PEG/PEO) manufactured by Agilent Technologies, Inc.
＜実施例２－１＞
農薬活性成分としてトリシクラゾール（Ｚ－３）４０部、結晶成長抑制剤（Ａ－１）２部、分散剤としてマレイン酸ジイソブチレン共重合物ナトリウム（ｂ－１）５部、凍結防止剤としてプロピレングリコール（Ｙ－１）５部、消泡剤としてシリコーン系消泡剤０．１部、及び市水５８部を混合した後、サンドグラインダーを用いて湿式粉砕し、水性分散液を調製した。更に、増粘剤としてモンモリロナイト系増粘剤（Ｙ－１０）２０部を混合し、均一な水性懸濁農薬組成物（Ｇ－１）を調製した。なお、結晶成長抑制剤の添加量は、有効成分である共重合体の重量を意味する。
<Example 2-1>
40 parts of tricyclazole (Z-3) as an agricultural chemical active ingredient, 2 parts of a crystal growth inhibitor (A-1), 5 parts of sodium diisobutylene maleate copolymer (b-1) as a dispersant, and propylene glycol as an antifreeze agent After mixing 5 parts of (Y-1), 0.1 part of a silicone antifoaming agent as an antifoaming agent, and 58 parts of city water, the mixture was wet pulverized using a sand grinder to prepare an aqueous dispersion. Furthermore, 20 parts of a montmorillonite-based thickener (Y-10) was mixed as a thickener to prepare a homogeneous aqueous pesticide suspension composition (G-1). The amount of the crystal growth inhibitor added means the weight of the copolymer which is the active ingredient.
＜実施例２－２～２－２４、比較例２－１～２－７＞
下記表３の組成とした他は実施例２－１と同様にして、実施例２－２～２－２４、比較例２－１～２－７の水性懸濁農薬組成物を作製した。
<Examples 2-2 to 2-24, Comparative Examples 2-1 to 2-7>
Aqueous pesticide suspension compositions of Examples 2-2 to 2-24 and Comparative Examples 2-1 to 2-7 were prepared in the same manner as in Example 2-1, except that the composition was as shown in Table 3 below.
表３に記載の各成分は以下の通りである。
農薬活性成分
Ｚ－１：チアメトキサム（４０００ｐｐｍ）
Ｚ－２：イミダクロプリド（４８０ｐｐｍ）
Ｚ－３：トリシクラゾール（５９６ｐｐｍ）
Ｚ－４：イマゼタピル（１４００ｐｐｍ）
分散剤
ｂ－１：マレイン酸ジイソブチレン共重合物ナトリウム
ｂ－２：ナフタレンスルホン酸ホルマリン縮合物ナトリウム
ｂ－３：ポリオキシエチレン（１４モル）トリスチリルフェニルエーテルサルフェートＮＨ４
ｂ－４：リグニンスルホン酸ナトリウム
ｂ－５：ポリオキシエチレン（１４モル）トリスチリルフェニルエーテル
凍結防止剤
Ｙ－１：プロピレングリコール
Ｙ－２：エチレングリコール
Ｙ－３：尿素
Ｙ－４：グリセリン
消泡剤
シリコーン系消泡剤
湿潤剤
Ｙ－６：アルキル（Ｃ１０－１４）ベンゼンスルホン酸ナトリウム
Ｙ－７：アルキル（Ｃ１０－１４）サルフェートナトリウム
Ｙ－８：ジオクチルスルホサクシネートナトリウム
Ｙ－９：ポリオキシエチレン（７モル）２級アルキルエーテル
増粘剤
Ｙ－１０：モンモリロナイト系増粘剤（クニミネ工業株式会社製のクニピア－Ｇを４％分散させた水溶液）
Ｙ－１１：キサンタンガム（ＤＳＰ五協フード＆ケミカル株式会社製のＫＥＬＺＡＮを２％分散させた水溶液）
Each component described in Table 3 is as follows.
Agricultural active ingredient Z-1: thiamethoxam (4000 ppm)
Z-2: imidacloprid (480 ppm)
Z-3: tricyclazole (596 ppm)
Z-4: Imazethapyr (1400 ppm)
Dispersant b-1: sodium diisobutylene maleate copolymer b-2: sodium naphthalenesulfonic acid formalin condensate b-3: polyoxyethylene (14 mol) tristyrylphenyl ether sulfate NH 4
b-4: sodium lignin sulfonate b-5: polyoxyethylene (14 mol) tristyrylphenyl ether antifreeze agent Y-1: propylene glycol Y-2: ethylene glycol Y-3: urea Y-4: glycerin antifoaming Agent Silicone Antifoam Wetting Agent Y-6: Sodium Alkyl (C10-14) Benzene Sulfonate Y-7: Sodium Alkyl (C10-14) Sulfate Y-8: Sodium Dioctyl Sulfosuccinate Y-9: Polyoxyethylene (7 mol) secondary alkyl ether thickener Y-10: montmorillonite-based thickener (aqueous solution in which 4% of Kunipia-G manufactured by Kunimine Industries Co., Ltd. is dispersed)
Y-11: xanthan gum (aqueous solution in which KELZAN manufactured by DSP Gokyo Food & Chemical Co., Ltd. is dispersed at 2%)
各水性懸濁農薬組成物の粉砕性及び粒子成長率を以下の方法にて試験した。その結果を下記表４に示す。なお、粉砕性の評価が悪い水性懸濁農薬組成物は粒子成長率の試験が実施できなかった。 The pulverizability and particle growth rate of each aqueous pesticide suspension composition were tested by the following methods. The results are shown in Table 4 below. It should be noted that the particle growth rate test could not be carried out for aqueous pesticide suspension compositions with poor pulverizability evaluation.
［粉砕性］
水性懸濁農薬組成物を水で希釈後、顕微鏡にて粒子の状態を観察し、粉砕性を評価した。
評価基準
○：粉砕後の粒子が均一に分散している。
×：粒子が凝集体を形成している。または粗大な結晶が析出している。
[Grindability]
After diluting the aqueous pesticide suspension composition with water, the state of the particles was observed under a microscope to evaluate the pulverizability.
Evaluation Criteria ◯: Particles after pulverization are uniformly dispersed.
x: Particles form aggregates. Or coarse crystals are deposited.
［粒子成長率（加速試験）］
水性懸濁農薬組成物を容量５０ｍｌのガラス製スクリュー管に５０ｍｌ入れて密封し、これを５４℃で１４日間放置した後、分散している粒子の粒子径（μｍ）を、レーザー回折／散乱式粒度分布測定装置（株式会社堀場製作所製のＬＡ－９６０）を用いて測定し（測定溶媒：イオン交換水）、下記式を用いて粒子成長率を算出して、下記の基準で評価した。
評価基準
◎◎：１０％未満
◎：１０％以上、２０％未満
○：２０％以上、５０％未満
×：５０％以上
[Particle growth rate (acceleration test)]
50 ml of the aqueous suspension pesticide composition was placed in a glass screw tube with a capacity of 50 ml, sealed, and allowed to stand at 54° C. for 14 days. Measurement was performed using a particle size distribution analyzer (LA-960 manufactured by Horiba, Ltd.) (measurement solvent: deionized water), the particle growth rate was calculated using the following formula, and evaluated according to the following criteria.
Evaluation criteria ◎◎: less than 10% ◎: 10% or more and less than 20% ○: 20% or more and less than 50% ×: 50% or more
［粒子成長率（サイクル試験）］
水性懸濁農薬組成物を容量５０ｍｌのガラス製スクリュー管に５０ｍｌ入れて密封し、これを４０℃で２日間、次に室温で２日間、また次に０℃で２日間放置するという操作を１ヶ月間繰り返した後、分散している粒子の粒子径（μｍ）を、レーザー回折／散乱式粒度分布測定装置（株式会社堀場製作所製のＬＡ－９６０）を用いて測定し（測定溶媒：イオン交換水）、上記式を用いて粒子成長率を算出して、下記の基準で評価した。
評価基準
◎◎：１０％未満
◎：１０％以上、２０％未満
○：２０％以上、５０％未満
×：５０％以上
[Particle growth rate (cycle test)]
50 ml of the pesticidal aqueous suspension composition was placed in a glass screw tube with a capacity of 50 ml, sealed, and left at 40° C. for 2 days, then at room temperature for 2 days, and then at 0° C. for 2 days. After repeating for months, the particle size (μm) of the dispersed particles was measured using a laser diffraction/scattering particle size distribution analyzer (LA-960 manufactured by Horiba, Ltd.) (measurement solvent: ion exchange water), the particle growth rate was calculated using the above formula, and evaluated according to the following criteria.
Evaluation criteria ◎◎: less than 10% ◎: 10% or more and less than 20% ○: 20% or more and less than 50% ×: 50% or more
実施例２－１～２－２４の水性懸濁農薬組成物は優れた粉砕性を有し、調製時の粒子の凝集等を防止できた。また、実施例２－１～２－２４の水性懸濁農薬組成物は経時的な粒子成長に対する優れた抑制効果を示した。一方、比較例２－１、２－３、及び２－５の水性懸濁農薬組成物は、構成単位（Ｓ１）のｎが２３より小さいため、経時的な粒子成長抑制効果が悪かった。比較例２－２では、構成単位（Ｓ１）のｎが１１４より大きいため、水性懸濁農薬組成物が加水粘性を有しており、製剤化出来なかった。比較例２－４の水性懸濁農薬組成物は、構成単位（Ｓ２）のＲ４が水素原子及びメチル基のいずれでもないため、粉砕性が悪かった。比較例２－６の水性懸濁農薬組成物は、構成単位（Ｓ２）を含有しないため、粉砕性が悪かった。比較例２－７の水性懸濁農薬組成物は、構成単位（Ｓ１）を含有しないため、粉砕性が悪かった。
The aqueous pesticide suspension compositions of Examples 2-1 to 2-24 had excellent pulverizability, and were able to prevent aggregation of particles during preparation. In addition, the aqueous pesticide suspension compositions of Examples 2-1 to 2-24 exhibited an excellent inhibitory effect on particle growth over time. On the other hand, the aqueous pesticide suspension compositions of Comparative Examples 2-1, 2-3, and 2-5 exhibited poor particle growth inhibition effects over time because n of the structural unit (S1) was smaller than 23. In Comparative Example 2-2, since n of the structural unit (S1) was greater than 114, the aqueous pesticidal suspension composition had viscosity with water and could not be formulated. The pesticidal aqueous suspension composition of Comparative Example 2-4 had poor pulverizability because R 4 of the structural unit (S2) was neither a hydrogen atom nor a methyl group. The pesticidal aqueous suspension composition of Comparative Example 2-6 did not contain the structural unit (S2), and therefore had poor grindability. The pesticidal aqueous suspension composition of Comparative Example 2-7 did not contain the structural unit (S1), and therefore had poor pulverizability.
Claims (9)
前記構成単位（Ｓ１）、前記構成単位（Ｓ２）、及び前記構成単位（Ｓ３）の合計を１００重量％とした場合に、前記構成単位（Ｓ１）が４９～８０重量％であり、前記構成単位（Ｓ２）が１９～５０重量％であり、前記構成単位（Ｓ３）が１～１５重量％であり、
前記構成単位（Ｓ１）、前記構成単位（Ｓ２）、及び前記構成単位（Ｓ３）はランダム共重合されていることを特徴とする結晶成長抑制剤。
（式中、Ｒ１は水素原子又はメチル基であり、Ｒ２Ｏは炭素数２～３のオキシアルキレン基であり、ｎは２３～１１４の整数であり、Ｒ３は炭素数１～８の炭化水素基である。）
（式中、Ｒ４は水素原子又はメチル基である。） Only the structural unit (S1) derived from the compound represented by the following formula 1, the structural unit (S2) derived from the compound represented by the following formula 2, and the structural unit (S3) derived from an unsaturated carboxylic acid having a molecular weight of 150 or less or an anhydride thereof containing a copolymer consisting of
When the total of the structural unit (S1), the structural unit (S2), and the structural unit (S3) is 100% by weight, the structural unit (S1) is 49 to 80% by weight, and the structural unit (S2) is 19 to 50% by weight, the structural unit (S3) is 1 to 15% by weight,
A crystal growth inhibitor , wherein the structural unit (S1), the structural unit (S2), and the structural unit (S3) are randomly copolymerized.
(wherein R 1 is a hydrogen atom or a methyl group, R 2 O is an oxyalkylene group having 2 to 3 carbon atoms, n is an integer of 23 to 114, and R 3 is a It is a hydrocarbon group.)
(Wherein, R4 is a hydrogen atom or a methyl group.)
前記農薬活性成分、前記結晶成長抑制剤、及び前記水の合計を１００重量％とした場合に、前記農薬活性成分が０．５～５０重量％であり、前記結晶成長抑制剤が０．１～１０重量％であり、前記水が４０～９９重量％である、請求項４に記載の農薬組成物。 further containing water,
When the sum of the agricultural chemical active ingredient, the crystal growth inhibitor, and the water is 100% by weight, the agricultural chemical active ingredient is 0.5 to 50% by weight, and the crystal growth inhibitor is 0.1 to 50% by weight. 10 % by weight and said water is 40-99% by weight.
前記結晶成長抑制剤は、下記式１で示される化合物由来の構成単位（Ｓ１）と下記式２で示される化合物由来の構成単位（Ｓ２）と分子量１５０以下の不飽和カルボン酸またはその無水物由来の構成単位（Ｓ３）のみからなる共重合体を含有し、 The crystal growth inhibitor is derived from a structural unit (S1) derived from a compound represented by the following formula 1, a structural unit (S2) derived from a compound represented by the following formula 2, and an unsaturated carboxylic acid having a molecular weight of 150 or less or an anhydride thereof. containing a copolymer consisting only of the structural unit (S3) of
前記共重合体の数平均分子量が２，０００～１００，０００であることを特徴とする農薬組成物。 The agricultural chemical composition, wherein the copolymer has a number average molecular weight of 2,000 to 100,000.
（式中、Ｒ(In the formula, R １1 は水素原子又はメチル基であり、Ｒis a hydrogen atom or a methyl group, and R ２2 Ｏは炭素数２～３のオキシアルキレン基であり、ｎは２３～１１４の整数であり、ＲO is an oxyalkylene group having 2 to 3 carbon atoms, n is an integer of 23 to 114, R ３3 は炭素数１～８の炭化水素基である。）is a hydrocarbon group having 1 to 8 carbon atoms. )
（式中、Ｒ(In the formula, R ４4 は水素原子又はメチル基である。）is a hydrogen atom or a methyl group. )
前記農薬活性成分、前記結晶成長抑制剤、及び前記水の合計を１００重量％とした場合に、前記農薬活性成分が０．５～５０重量％であり、前記結晶成長抑制剤が０．１～１０重量％であり、前記水が４０～９９重量％である、請求項６から８のいずれか一項に記載の農薬組成物。 When the sum of the agricultural chemical active ingredient, the crystal growth inhibitor, and the water is 100% by weight, the agricultural chemical active ingredient is 0.5 to 50% by weight, and the crystal growth inhibitor is 0.1 to 50% by weight. 10% by weight and said water is 40-99% by weight.
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