JPH0225882B2 - - Google Patents
Info
- Publication number
- JPH0225882B2 JPH0225882B2 JP7256183A JP7256183A JPH0225882B2 JP H0225882 B2 JPH0225882 B2 JP H0225882B2 JP 7256183 A JP7256183 A JP 7256183A JP 7256183 A JP7256183 A JP 7256183A JP H0225882 B2 JPH0225882 B2 JP H0225882B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- average molecular
- molecular weight
- polymer
- lactic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920000642 polymer Polymers 0.000 claims description 36
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 26
- 238000005507 spraying Methods 0.000 claims description 9
- 239000000575 pesticide Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 229930182843 D-Lactic acid Natural products 0.000 claims 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 26
- 235000014655 lactic acid Nutrition 0.000 description 13
- 239000004310 lactic acid Substances 0.000 description 13
- -1 Polyoxyethylene Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 239000000642 acaricide Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000207199 Citrus Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 235000020971 citrus fruits Nutrition 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012872 agrochemical composition Substances 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- MMUFAGXJPKNAHT-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1 MMUFAGXJPKNAHT-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は徐放性重合体を含有する葉面散布用農
薬組成物に関する。さらに詳細には本発明はα−
脂肪族オキシ酸ポリエステルのうち、特にグリコ
ール酸、乳酸の重合体、特に重量平均分子量がそ
れぞれ3000〜30000、1000〜10000の範囲にある、
葉面散布用農薬組剤として極めて有用な徐放性重
合体を含有する葉面散布用農薬組成物に関する。
本発明に係るグリコール酸重合体および乳酸重
合体は加水分解性であつて、作物上で特に水分に
よつて分解消失し、環境中に残留蓄積しないこと
および分解過程中で主剤の農薬を徐々に放出する
ことによつて薬効の持続性を発揮し得ることなど
が主たる特徴である。
グリコール酸重合体および乳酸重合体を農薬に
使用して主剤の放出を調節し得ることは、例えば
米国特許第3976071号明細書にも記載されている
ように公知である。しかしながら既往の研究にお
いては、本発明者等が最重要点と考える重合度と
好ましい薬効、就中残効性付与との関係について
は全く明らかにされていないばかりでなく、これ
ら重合体を無選択に使用する場合には却つて薬効
を著しく損うということも何ら認識されていな
い。
本発明者等は特に殺ダニ剤、殺菌剤、殺虫剤の
ように作物の葉面に散布する形態の、徐放性重合
体を含有する農薬製剤の使用に当つては、グリコ
ール酸重合体および乳酸重合体の重量平均分子量
がそれぞれ3000〜30000および1000〜10000の範囲
にあることが好ましく、その前後に於ては添加効
果の向上がなく、特に重量平均分子量がそれぞれ
上記の範囲を超過する場合は薬効の低減する発現
することを見出して本発明を完成した。
本発明に用いられるグリコール酸重合体および
乳酸重合体は米国特許第2616945号明細書に記載
の方法によつて合成することができる。その合成
法の一例と基本的性質および加水分解性について
説明する。
出発物質である乳酸100ｇに0.1ｇの三酸化アン
チモン（Sb2O3）触媒を側管と窒素導入キヤピラ
リを付けたフラスコ中で200℃の温度で反応させ
ると水が激しく留出してくる。水の留出が遅くな
つたときに減圧度を５mmHg以下にするとラクチ
ド（環状二量体）が約70ｇ留出する。得られたラ
クチドを酢酸エチルで二回再結晶することにより
製精し、これをオクチル酸スズを触媒として、減
圧下160〜200℃の温度範囲で種々の時間、開環重
合した。得られたポリマーの分子量は1000〜
70000であり、アセトン、トルエン、クロロホル
ム、ベンゼン等に溶解したが、メタノール、エタ
ノールには若干、膨潤する程度であり、水には全
く溶解しなかつた。また25℃の蒸留水に、その成
型品（２×５×0.5mm）を浸漬放置したところ、
下の表に示すように加水分解した。
The present invention relates to a pesticide composition for foliar spraying containing a sustained release polymer. More specifically, the present invention provides α-
Among aliphatic oxyacid polyesters, especially polymers of glycolic acid and lactic acid, especially those having weight average molecular weights in the range of 3000 to 30000 and 1000 to 10000, respectively.
The present invention relates to an agrochemical composition for foliar spraying containing a sustained release polymer which is extremely useful as an agrochemical composition for foliar spraying. The glycolic acid polymer and lactic acid polymer according to the present invention are hydrolyzable and are decomposed and disappeared on crops, especially when exposed to moisture, and do not accumulate in the environment and gradually release the main pesticide during the decomposition process. Its main feature is that it can maintain its medicinal efficacy by releasing it. It is known that glycolic acid and lactic acid polymers can be used in pesticides to control the release of the base agent, as also described for example in US Pat. No. 3,976,071. However, in existing studies, not only has the relationship between the degree of polymerization and desirable drug efficacy, especially imparting residual efficacy, which the present inventors consider the most important point, not been clarified at all, but also these polymers have not been selected. There is also no recognition that when used for treatment, the medicinal efficacy is significantly impaired. The present inventors particularly recommend that when using agrochemical formulations containing slow-release polymers, such as acaricides, fungicides, and insecticides, which are sprayed on the leaves of crops, glycolic acid polymers and It is preferable that the weight average molecular weight of the lactic acid polymer is in the range of 3000 to 30000 and 1000 to 10000, respectively, and there is no improvement in the addition effect before or after that, especially when the weight average molecular weight exceeds the above range. The present invention was completed based on the discovery that the drug's efficacy was reduced. The glycolic acid polymer and lactic acid polymer used in the present invention can be synthesized by the method described in US Pat. No. 2,616,945. An example of its synthesis method, basic properties, and hydrolyzability will be explained. When 100 g of the starting material lactic acid is reacted with 0.1 g of antimony trioxide (Sb 2 O 3 ) catalyst at a temperature of 200° C. in a flask equipped with a side pipe and a nitrogen introduction capillary, water is violently distilled out. When water distillation becomes slow, if the degree of vacuum is reduced to 5 mmHg or less, about 70 g of lactide (cyclic dimer) will be distilled out. The obtained lactide was purified by recrystallizing twice with ethyl acetate, and ring-opening polymerization was performed using tin octylate as a catalyst at a temperature range of 160 to 200° C. under reduced pressure for various times. The molecular weight of the obtained polymer is 1000~
70,000 and dissolved in acetone, toluene, chloroform, benzene, etc., but only slightly swelled in methanol and ethanol, and did not dissolve in water at all. Also, when the molded product (2 x 5 x 0.5 mm) was immersed in distilled water at 25°C,
Hydrolyzed as shown in the table below.
【表】
またこれらの重合体に２，４−Ｄを添加し、25
℃の蒸留水の中で放出試験を行い、UV吸収スペ
クトルで定量した結果から、主剤の放出速度は重
合体の分子量によつて調節されていることが明白
である。[Table] In addition, 2,4-D was added to these polymers, and 25
From the results of a release test conducted in distilled water at ℃ and quantified by UV absorption spectroscopy, it is clear that the release rate of the base agent is controlled by the molecular weight of the polymer.
【表】 結果を下記に示す。【table】 The results are shown below.
【表】
またグリコール酸重合体についても同様にして
製造することができ、また２，４−Ｄ添加による
同様な放出の傾向が認められた。
つぎに製剤の具体例について説明する。
実施例 １
乳剤 (1)
重量平均分子量2000の乳酸重合体40重量部を三
フツ化酢酸54重量部に溶解し、これに乳化剤とし
てポリエキシエチレンアルキルエーテル1.6部、
ポリオキシエチレンアルキルフエノールエーテル
2.3部、アルキルベンゼンスルホン酸塩2.1部と混
合溶解し、乳剤原液を得る。本液と農薬の乳剤と
共に散布液中に混合乳化し乳酸重合体と農薬の乳
化散布液とする。
実施例 ２
乳剤 (2)
重量平均分子量8000のグリコール酸重合体20重
量部を三フツ化酢酸47.8重量部、イソホロン25重
量部に溶解し、これに乳化剤としてポリオキシエ
チレンアルキルフイノールエーテル2.1部、ポリ
オキシエチレンアルキルエーテル2.3部、アルキ
ルベンゼンスルホン酸塩2.8部を混合溶解し乳剤
原液を得る。本液を農薬の水和剤と共に散布液中
に乳化、分散せしめ、グリコール酸重合体と農薬
の散布液とする。
実施例 ３
水和剤
重量平均分子量1500の乳酸重合体20部をアセト
ン70部に溶解し、これに８−ヒドロキシキノリン
銅20部を加へ撹拌し分散する。本液をクレー52部
中に混合し、噴霧し、アセトンを除去し混合粉体
を得る。本粉末に分散剤としてポリオキシエチレ
ンアルキルフエノールエーテル３部、リグニンス
ルホン酸塩５部を加へ全体をよく混合後粉砕し水
和剤を得る。本剤を所定量の水に分散させ散布液
とする。
つぎにグリコール酸重合体および乳酸重合体を
使用して殺ダニ剤、殺虫剤、殺菌剤に添加、製剤
して作物の地上部に散布する場合、効力の増強に
最も好ましい重合度の範囲を選抜するに至つた過
程を試験例を以つて説明する。
試験例１ 殺ダニ剤に使用した場合
作物のハダニは年間を通じて発生加害するた
め、最少の散布回数で有効に防除することが要望
される。薬効の持続性に大きく関係する要因に耐
雨性の向上がある。殺ダニ剤として使用されてい
るクロルベンジレート（ｐ，p′−ジクロロベンジ
ル酸エチル）乳剤の散布液中に本発明に係る重合
体１％を混合し、散布後に１時間、１mmの人工降
雨を降らし薬剤の耐雨性をハダニ（Tetranychus
telarlus）に対する薬効を以つて検定した。こゝ
に耐雨性を評価するための耐雨係数は次式
耐雨係数＝無降雨区のLC50／降雨区のLC50
であらわされる。即ち雨に強い場合は耐雨係数は
１に近づく。[Table] Glycolic acid polymers can also be produced in the same manner, and a similar release tendency was observed with the addition of 2,4-D. Next, specific examples of formulations will be explained. Example 1 Emulsion (1) 40 parts by weight of a lactic acid polymer having a weight average molecular weight of 2000 was dissolved in 54 parts by weight of trifluoroacetic acid, and 1.6 parts of polyexyethylene alkyl ether was added as an emulsifier.
Polyoxyethylene alkyl phenol ether
Mix and dissolve 2.3 parts and 2.1 parts of alkylbenzene sulfonate to obtain an emulsion stock solution. This solution is mixed and emulsified with an emulsion of agricultural chemicals in a spray solution to form an emulsified spray solution of lactic acid polymer and pesticide. Example 2 Emulsion (2) 20 parts by weight of a glycolic acid polymer having a weight average molecular weight of 8,000 was dissolved in 47.8 parts by weight of trifluoroacetic acid and 25 parts by weight of isophorone, and 2.1 parts of polyoxyethylene alkyl finol ether was added as an emulsifier. Mix and dissolve 2.3 parts of polyoxyethylene alkyl ether and 2.8 parts of alkylbenzene sulfonate to obtain an emulsion stock solution. This solution is emulsified and dispersed in a spray solution together with a hydrating agent for the agricultural chemical to form a spray solution containing the glycolic acid polymer and the pesticide. Example 3 Wettable powder 20 parts of a lactic acid polymer having a weight average molecular weight of 1500 is dissolved in 70 parts of acetone, and 20 parts of 8-hydroxyquinoline copper is added thereto and dispersed with stirring. This solution is mixed in 52 parts of clay, sprayed, and acetone is removed to obtain a mixed powder. To this powder were added 3 parts of polyoxyethylene alkyl phenol ether and 5 parts of lignin sulfonate as a dispersant, and the whole was thoroughly mixed and pulverized to obtain a wettable powder. Disperse this agent in a specified amount of water to make a spray liquid. Next, when adding and formulating acaricides, insecticides, and fungicides using glycolic acid polymers and lactic acid polymers and spraying them on the above-ground parts of crops, we selected the range of polymerization degree most preferable for increasing efficacy. The process that led to this will be explained using test examples. Test Example 1 When used as an acaricide Spider mites occur on crops throughout the year, so it is desired to effectively control them with a minimum number of sprayings. Improvement in rain resistance is a factor that greatly affects the sustainability of medicinal efficacy. 1% of the polymer according to the present invention was mixed into the spray solution of chlorobenzylate (p,p'-ethyl dichlorobenzilate) emulsion used as an acaricide, and 1 mm of artificial rain was applied for 1 hour after spraying. The rain resistance of the raindrop agent
The medicinal efficacy against P. telarlus was tested. The rain resistance coefficient for evaluating rain resistance is expressed by the following formula: Rain resistance coefficient = LC50 of no rainfall area/LC50 of rain area. That is, if the material is resistant to rain, the rain resistance coefficient approaches 1.
【表】【table】
【表】【table】
【表】
以上の結果からグリコール酸重合体、乳酸重合
体共耐雨性向上と重合体の重量平均分子量との関
係には一定の傾向が得られた。即ち、好ましい重
量平均分子量の範囲としてはグリコール酸重合体
については3000〜30000、乳酸重合体については
1000〜10000の範囲であり、その前後では添加効
果は殆ど認められなかつた。
試験例２ 殺菌剤に使用した場合
作物病害防除には例えば柑橘カイヨウ病防除の
場合、散布は１ケ月間隔と長期に亘り、且つ半年
に亘る発生期間がある為、殺菌剤の散布に当つて
薬効の持続性が強く要望される。
本試験に於いては柑橘カイヨウ病
（Xanthomonas cltrl）の防除効果増強に本発明
に係る重合体の好ましい重量平均分子量範囲を検
索した。[Table] From the above results, a certain tendency was obtained in the relationship between the rain resistance improvement of glycolic acid polymer and lactic acid polymer and the weight average molecular weight of the polymer. That is, the preferred weight average molecular weight range is 3000 to 30000 for glycolic acid polymers, and 3000 to 30000 for lactic acid polymers.
It was in the range of 1,000 to 10,000, and almost no effect of addition was observed before and after that. Test Example 2 When used as a fungicide In the case of crop disease control, for example, in the case of citrus chiliosis control, spraying is carried out over a long period of time, with intervals of one month, and there is an outbreak period of half a year. Sustainability is strongly desired. In this test, we searched for a preferable weight average molecular weight range of the polymer according to the present invention to enhance the control effect on citrus leaf blight (Xanthomonas cltrl).
【表】【table】
【表】
甘夏成木１区１樹について５月12日、６月20日
に散布し、７月25日に１樹当り100葉当りのカイ
ヨウ病の罹病葉数を調査した。
試験結果[Table] One tree in one ward of Amanatsu mature trees was sprayed on May 12th and June 20th, and on July 25th, the number of leaves affected by Kaiyou disease per 100 leaves per tree was investigated. Test results
【表】【table】
【表】
以上の結果から柑橘カイヨウ病防除効果には添
加する各重合体間に明らかな重量平均分子量の選
択性が見られる。即ち好ましい範囲としてはグリ
コール酸重合体重量平均分子量3000〜30000、乳
酸重合体重量平均分子量1000〜10000の間にあつ
てこの間に特に差は見られない。[Table] From the above results, it can be seen that there is clear selectivity in weight average molecular weight between the added polymers in the citrus canker blight control effect. That is, the preferred range is a weight average molecular weight of glycolic acid polymer of 3,000 to 30,000 and a weight average molecular weight of lactic acid polymer of 1,000 to 10,000, with no particular difference observed between them.
Claims (1)
乳酸重合体および重量平均分子量が3000〜30000
の範囲にあるグリコール酸重合体の１種ないし２
種以上の重合体と葉面散布用農薬とを含有するこ
とを特徴とする葉面散布用農薬組成物。1 Lactic acid polymer with a weight average molecular weight in the range of 1,000 to 10,000 and a weight average molecular weight in the range of 3,000 to 30,000
One or two glycolic acid polymers within the range of
A pesticide composition for foliar spraying, characterized in that it contains a polymer of at least one species and a pesticide for foliar spraying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7256183A JPS59199604A (en) | 1983-04-25 | 1983-04-25 | Agricultural chemical composition for foliar application containing delayed-release polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7256183A JPS59199604A (en) | 1983-04-25 | 1983-04-25 | Agricultural chemical composition for foliar application containing delayed-release polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59199604A JPS59199604A (en) | 1984-11-12 |
| JPH0225882B2 true JPH0225882B2 (en) | 1990-06-06 |
Family
ID=13492895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7256183A Granted JPS59199604A (en) | 1983-04-25 | 1983-04-25 | Agricultural chemical composition for foliar application containing delayed-release polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59199604A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4813997B1 (en) * | 1987-04-06 | 1995-07-18 | Cpc International Inc | Method for regulating plant growth |
| JP2002104904A (en) * | 2000-09-29 | 2002-04-10 | Toyobo Co Ltd | Sustained release pesticide composition |
-
1983
- 1983-04-25 JP JP7256183A patent/JPS59199604A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59199604A (en) | 1984-11-12 |
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