JPH0430361B2 - - Google Patents
Info
- Publication number
- JPH0430361B2 JPH0430361B2 JP9881484A JP9881484A JPH0430361B2 JP H0430361 B2 JPH0430361 B2 JP H0430361B2 JP 9881484 A JP9881484 A JP 9881484A JP 9881484 A JP9881484 A JP 9881484A JP H0430361 B2 JPH0430361 B2 JP H0430361B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- pendimethalin
- granular
- phenyl
- herbicide composition
- 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
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 21
- 230000002363 herbicidal effect Effects 0.000 claims description 17
- 239000004009 herbicide Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000005591 Pendimethalin Substances 0.000 description 38
- 239000008187 granular material Substances 0.000 description 23
- 239000008186 active pharmaceutical agent Substances 0.000 description 11
- 229940088679 drug related substance Drugs 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- -1 Generally Substances 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 6
- 238000005054 agglomeration Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000007711 solidification Methods 0.000 description 6
- 230000008023 solidification Effects 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- FLWSNJAEMMOZJG-UHFFFAOYSA-N 1,2-dimethyl-4-(1-phenylethyl)benzene Chemical compound C=1C=C(C)C(C)=CC=1C(C)C1=CC=CC=C1 FLWSNJAEMMOZJG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- LVUFHDXEVLCSII-UHFFFAOYSA-N 1,3-dimethyl-5-(1-phenylethyl)benzene Chemical compound C=1C(C)=CC(C)=CC=1C(C)C1=CC=CC=C1 LVUFHDXEVLCSII-UHFFFAOYSA-N 0.000 description 2
- RZCMUIOJBYCKPG-UHFFFAOYSA-N 1-benzyl-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(CC=2C=CC=CC=2)=C1 RZCMUIOJBYCKPG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000009422 growth inhibiting effect Effects 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GTACQJHQXAMGPH-UHFFFAOYSA-N (2-methyl-1-phenylpropan-2-yl)benzene Chemical class C=1C=CC=CC=1C(C)(C)CC1=CC=CC=C1 GTACQJHQXAMGPH-UHFFFAOYSA-N 0.000 description 1
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 description 1
- OXUCVRVGEUHXIF-UHFFFAOYSA-N 1,3-diethyl-5-(1-phenylethyl)benzene Chemical compound CCC1=CC(CC)=CC(C(C)C=2C=CC=CC=2)=C1 OXUCVRVGEUHXIF-UHFFFAOYSA-N 0.000 description 1
- RAIHKDDVBZEGOW-UHFFFAOYSA-N 1,3-dimethyl-2-(1-phenylethyl)benzene Chemical compound CC=1C=CC=C(C)C=1C(C)C1=CC=CC=C1 RAIHKDDVBZEGOW-UHFFFAOYSA-N 0.000 description 1
- FRAOOIFTSMORED-UHFFFAOYSA-N 1,4-dimethyl-2-(1-phenylethyl)benzene Chemical compound C=1C(C)=CC=C(C)C=1C(C)C1=CC=CC=C1 FRAOOIFTSMORED-UHFFFAOYSA-N 0.000 description 1
- CVAMMFFQVDUIEX-UHFFFAOYSA-N 1-benzyl-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1CC1=CC=CC=C1 CVAMMFFQVDUIEX-UHFFFAOYSA-N 0.000 description 1
- JOUBGGHXBLOLFY-UHFFFAOYSA-N 2,4-dimethyl-1-(1-phenylethyl)benzene Chemical compound C=1C=C(C)C=C(C)C=1C(C)C1=CC=CC=C1 JOUBGGHXBLOLFY-UHFFFAOYSA-N 0.000 description 1
- GKGTVJOYFGUPSA-UHFFFAOYSA-N 2,4-dimethylpentan-3-ylbenzene Chemical compound CC(C)C(C(C)C)C1=CC=CC=C1 GKGTVJOYFGUPSA-UHFFFAOYSA-N 0.000 description 1
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical class C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- TVJFOXNCNDDITD-UHFFFAOYSA-N 3-benzylpentan-3-ylbenzene Chemical class C=1C=CC=CC=1C(CC)(CC)CC1=CC=CC=C1 TVJFOXNCNDDITD-UHFFFAOYSA-N 0.000 description 1
- IWSSFULMLQTJFO-UHFFFAOYSA-N 4-benzyl-1,2-dimethylbenzene Chemical compound C1=C(C)C(C)=CC=C1CC1=CC=CC=C1 IWSSFULMLQTJFO-UHFFFAOYSA-N 0.000 description 1
- GABKUOUOOZYHIR-UHFFFAOYSA-N 4-benzylheptan-4-ylbenzene Chemical class CCCC(CCC)(Cc1ccccc1)c1ccccc1 GABKUOUOOZYHIR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 1
- 235000005476 Digitaria cruciata Nutrition 0.000 description 1
- 235000006830 Digitaria didactyla Nutrition 0.000 description 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 244000025670 Eleusine indica Species 0.000 description 1
- 235000014716 Eleusine indica Nutrition 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 240000001341 Reynoutria japonica Species 0.000 description 1
- 235000018167 Reynoutria japonica Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
発明の技術分野
本発明は、Ｎ−（１−エチルプロピル）−３，４
−ジメチル−２，６−ジニトロアニリン〔以下、
ペンデイメタリンと称する。〕を活性成分として
含有する畑作用粒状除草剤組成物に関するもので
ある。
技術的背景
ペンデイメタリンは、畑地一年生イネ科・広葉
雑草に幅広くかつ長期間高い除草効果を有するこ
とから、近年広く使用されているジニトロアニリ
ン系の非ホルモン型吸収移行型除草剤であり、ま
た、ペンデイメタリンは強い黄色を呈する化合物
である。現在、ペンデイメタリンを用いた製剤と
して、乳剤、水和剤があり、使用されている。し
かし、散布時の操作面で乳剤、水和剤より簡便な
粒状剤の開発が望まれている。粒状剤としては、
一般に、10〜48メツシユの粒剤、48〜150メツシ
ユの微粒剤、65〜250メツシユの微粒剤Ｆが実用
化されているが、ペンデイメタリンは畑作用であ
ることから、粒剤では均一散布が困難であり、微
粒剤や微粒剤Ｆでは微細部分が多く、目的地外へ
のドリフト等があり、32〜100メツシユの範囲の
細粒剤の開発が特に求められている。
先行技術
ペンデイメタリンの如き固状農薬活性成分の粒
状剤を作る際には、従来、(1)練込法、(2)被覆法、
(3)吸着法等の方法により製造されている。ペンデ
イメタリンの場合、(1)練込法では装置への着色が
見られ、次に他の製品を製造する際には装置各部
の徹底的な洗浄を要するなど、製造工程での不便
が生じ、(2)被覆法ではペンデイメタリン原体を微
粉化しておく必要があり、粉砕時、(1)と同様な問
題がある。以上により、ペンデイメタリンの場
合、(3)吸着法で製造する必要が生じるが、吸着法
においても、ペンデイメタリン原体を溶解し、か
つ、揮発性、刺激性、臭気性等のない溶剤が不可
欠である。
固状濃薬活性成分を吸着法によつて粒状剤にす
る際には種々の方法が知られている。たとえば、
エチレングリコールのようなグリコール類を用い
る方法（特開昭52−110832号公報）、または、グ
リセリン、ジエチレングリコール等の不揮発性溶
媒を用いた方法（特開昭52−117432号公報）があ
る。しかし、これら従来の方法では、溶解性また
は製造時の吸着むら、団粒化さらに製造後の固化
等がみられ、ペンデイメタリンに用いる事ができ
ない。さらに、ペンデイメタリンは、シクロヘキ
サノン、ソルベントナフサ、キシレン、Ｎ−メチ
ル−２−ピロリドン等に溶解し、製剤できるが、
溶剤の揮発による製剤の固化や効果の低下により
使用ができないので、他の溶剤又は、方法が望ま
れている。
発明の目的
本発明の目的は、ペンデイメタリンを溶解し、
粒状剤として製造し得る溶剤を提供することおよ
び長期間保存後の団粒化および固化のない除草効
果のすぐれた粒状剤を提供することである。
発明の構成
本発明は、
Ａ 粒状担体に、
Ｂ(i) ペンデイメタリンおよび
(ii) 一般式
（式中R1は水素原子またはメチル基、R2お
よびR3は炭素数１〜４個の低級アルキル基
である）
で示される１種または２種以上の化合物を担持さ
せてなることを特徴とする畑作用粒状除草剤組成
物である。
本発明の構成要素について以下に詳しく説明す
る。
（粒状担体）
本発明で用いられる粒状担体としては、硅砂、
軽石、炭酸カルシウム等の天然物、また、造粒品
でも良い。また、その粒度としては、10〜250メ
ツシユ、好ましくは、32〜100メツシユのもので
あり、特に32〜100メツシユの範囲のものを95重
量％以上含むものが好適である。また、目的によ
り、単独又は２種以上を混合して用いても良い。
（ペンデイメタリン）
本発明に使用する農薬活性成分であるペンデイ
メタリンは粒状除草剤組成物全量の0.1〜10.0重
量％で用いられるが、好ましくは、0.5〜5.0重量
％で用いるのが良い。
（一般式で示される化合物）
本発明に用いられる一般式で示される化合物
は、フエニルジメチルフエニルエタン類、フエニ
ルジメチルフエニルメタン類、フエニルジエチル
フエニルエタン類、フエニルジプロピルフエニル
エタン類、また、フエニルジブチルフエニルエタ
ン類等があり、たとえば、フエニル２，３−ジメ
チルフエニルエタン、フエニル２，４−ジメチル
フエニルエタン，フエニル２，５−ジメチルフエ
ニルエタン、フエニル２，６−ジメチルフエニル
エタン、フエニル３，４−ジメチルフエニルエタ
ン、フエニル３，５−ジメチルフエニルエタン、
フエニル２，４−ジメチルフエニルメタン、フエ
ニル３，４−ジメチルフエニルメタン、フエニル
３，５−ジメチルフエニルメタン、フエニル３，
５−ジブチルフエニルエタン、フエニル３，５−
ジイソプロピルフエニルメタン等を挙げることが
でき、これらは単独で用いても良く、２種以上を
併用してもよい。ただし、これら例示の化合物に
必ずしも限定されるものではない。
本発明で用いられる一般式で示される化合物
は一般的な溶剤と同様に取扱つてよい。また、使
用する添加量は粒状除草剤組成物全量の0.2〜
10.0重量％でよく、好ましくは0.5〜5.0重量％で
ある。
（その他の添加剤）
また、本発明において支障のない限り、たとえ
ば、タルク、クレー、ホワイトカーボン等の微粉
末、ベンガラ、モリブデン青、チタンホワイトな
どの顔料、メチレンブルー、ローダミンＢなどの
着色剤、ポリオキシエチレンアルキルフエニルエ
ーテルサルフエートアンモニウム塩、ポリオキシ
エチレンアルキルエーテルサルフエートアンモニ
ウム塩、ジアルキルスルホこはく酸エステルソー
ダ塩などの界面活性剤等を必要により添加するこ
とができる。また、本発明においては、他の除草
剤、殺虫剤、殺菌剤などの農薬成分を添加するこ
とができる。
本発明の効果
本発明のペンデイメタリン畑作用粒状除草剤
は、
(1) 畑土壌での有効成分の拡散が良好なため、除
草効果の均一化、向上が得られる。
(2) 製品を長期間貯蔵した際の団粒化、固化が認
められず、粒状剤として求められるところの物
理化学的性質が良好である。
(3) 溶剤の揮散性、臭気性等に問題がないことよ
り、製造時にその危険性等に特別な注意を払う
必要がなく、有利である。
などの優れた面を有するものである。
実施例
次に本発明の実施例および試験例を挙げ、具体
的に説明するが、実施例は、本発明を何ら制限す
るものではない。また、以下に示す部又は％は、
重量部又は重量％を表わす。
実施例 １
混合機に32〜100メツシユに篩分けした粒状の
軽石96部を入れ、これに、フエニル３，４−ジメ
チルフエニルエタン３部にペンデイメタリン原体
１部をあらかじめ加熱溶解した溶液を注加し、15
分間混合し、ペンデイメタリン１％を含有する粒
状剤を得た。
実施例 ２
混合機に実施例１で用いた粒状担体96部を入
れ、これに、フエニル３，５−ジメチルフエニル
エタン２部にペンデイメタリン原体２部をあらか
じめ加熱溶解した溶液を注加し、15分間混合し、
ペンデイメタリン２％を含有する粒状剤を得た。
実施例 ３
混合機に実施例１で用いた粒状担体93部を入
れ、これに、フエニル３，５−ジエチルフエニル
エタン３部にペンデイメタリン原体４部をあらか
じめ加熱溶解した溶液を注加し、15分間混合し、
ペンデイメタリン４％を含有する粒状剤を得た。
実施例 ４
混合機に実施例１で用いた粒状担体95部を入
れ、これに、フエニル３，５−ジイソプロピルフ
エニルエタン３部にペンデイメタリン原体２部を
あらかじめ加熱溶解した溶液を注加し、15分間混
合し、ペンデイメタリン２％を含有する粒状剤を
得た。
実施例 ５
混合機に実施例１で用いた粒状担体94部を入
れ、これに、フエニル３，４−ジメチルフエニル
エタン２部とフエニル３，５−ジメチルフエニル
メタン２部の混合液にペンデイメタリン原体２部
をあらかじめ加熱溶解した溶液を注加し、15分間
混合し、ペンデイメタリン２％を含有する粒状剤
を得た。
実施例 ６
混合機に32〜100メツシユに篩分けした粒状の
硅砂94部を入れ、これにフエニル３，５−ジブチ
ルフエニルエタン２部にペンデイメタリン原体２
部をあらかじめ加熱溶解した溶液を注加し、15分
間混合し、その後、ホワイトカーボン２部を添加
し、さらに15分間混合し、ペンデイメタリン２％
を含有する粒状剤を得た。
比較例 １
混合機に実施例１で用いた粒状担体95部を入
れ、これに、ポリエチレングリコール（平均分子
量400）４部にペンデイメタリン原体１部を加熱
混合した液を注加し、15分間混合した。けれど
も、均一に吸着できず、さらに団粒化した。その
ため、この例では製剤できなかつた。
比較例 ２
混合機に実施例１で用いた粒状担体95部を入
れ、これに、Ｎ−メチル−２−ピロリドン３部に
ペンデイメタリン１部をあらかじめ加熱溶解した
溶液を注加し、15分間混合し、ペンデイメタリン
１％を含有する粒状剤を得た。
比較例 ３
混合機に実施例１で用いた粒状担体95部を入
れ、これに、キシレン３部にペンデイメタリン原
体２部をあらかじめ加熱溶解した溶液を注加し、
15分間混合し、ペンデイメタリン２％を含有する
粒状剤を得た。
比較例 ４
混合機に実施例１で用いた粒状担体94部を入
れ、これに、Ｎ−メチル−２−ピロリドン２部に
ペンデイメタリン原体４部をあらかじめ加熱溶解
した溶液を注加し、15分間混合し、ペンデイメタ
リン４％を含有する粒状剤を得た。
比較例 ５
混合機に実施例１で用いた粒状担体95.5部を入
れ、これに、Ｎ−メチル−２−ピロリドン0.5部
と大豆油２部の混合液にペンデイメタリン原体２
部をあらかじめ加熱溶解させた溶液を注加し、15
分間混合し、ペンデイメタリン２％を含有する粒
状剤を得た。
比較例 ６
混合機に実施例５で用いた粒状担体94部を入
れ、これに、シクロヘキサノン２部にペンデイメ
タリン原体２部をあらかじめ加熱溶解した溶液を
注加し、15分間混合し、その後、ホワイトカーボ
ン２部を添加し、さらに、15分間混合し、ペンデ
イメタリン２％を含有する粒状剤を得た。
試験例 １
〔加圧貯蔵後の固化試験〕
実施例１〜６、比較例２〜６により製造したペ
ンデイメタリン粒状剤20ｇを内径6.0〜6.5cmのガ
ラス製円柱容器（底なし）に入れ、25ｇ／cm2にな
るよう鉄製重を乗せ加圧する。これを室温と50℃
に各々保存し、１日後および５日後に、円柱容器
をはずし、固化状態を観察する。次の判定基準に
より判定した結果を第１表に示す。
判定基準
−：団粒化なく、良好な流動性を有する。
＋：一部に団粒化が認められる。
≠：全体に団粒化が認められ、流動性を失なう。
Technical field of the invention The present invention relates to N-(1-ethylpropyl)-3,4
-dimethyl-2,6-dinitroaniline [hereinafter,
It is called pendimethalin. ] This relates to a granular herbicide composition for field use containing as an active ingredient. Technical background Pendimethalin is a dinitroaniline non-hormonal translocation herbicide that has been widely used in recent years because it has a wide and long-term high herbicidal effect on annual grass and broad-leaved weeds in upland fields. , pendimethalin is a compound that exhibits a strong yellow color. Currently, there are emulsions and wettable powders that are used as preparations using pendimethalin. However, it is desired to develop a granular formulation that is easier to operate during dispersion than emulsions and wettable powders. As a granule,
Generally, granules of 10 to 48 mesh, fine granules of 48 to 150 mesh, and fine granules F of 65 to 250 mesh have been put into practical use, but since pendimethalin is grown in the field, granules are uniformly distributed. However, it is difficult to use fine granules and fine granules F, which have a large number of fine particles and may drift outside the destination, so there is a particular need for the development of fine granules in the range of 32 to 100 meshes. Prior Art When making granules of solid pesticide active ingredients such as pendimethalin, conventional methods include (1) kneading method, (2) coating method,
(3) Manufactured by methods such as adsorption. In the case of pendimethalin, (1) the kneading method resulted in coloring of the equipment, which caused inconvenience in the manufacturing process, such as requiring thorough cleaning of each part of the equipment when manufacturing other products. (2) In the coating method, it is necessary to pulverize the pendimethalin drug substance, which causes the same problem as (1) when pulverizing. As a result of the above, in the case of pendimethalin, it is necessary to manufacture it by (3) adsorption method, but even in the adsorption method, a solvent that dissolves pendimethalin drug substance and is not volatile, irritating, odoriferous, etc. is essential. Various methods are known for forming solid concentrated active ingredients into granules by adsorption. for example,
There is a method using glycols such as ethylene glycol (Japanese Unexamined Patent Publication No. 52-110832), or a method using nonvolatile solvents such as glycerin or diethylene glycol (Japanese Unexamined Patent Publication No. 52-117432). However, these conventional methods cannot be used for pendimethalin because of uneven solubility or adsorption during production, agglomeration, and solidification after production. Furthermore, pendimethalin can be formulated by dissolving it in cyclohexanone, solvent naphtha, xylene, N-methyl-2-pyrrolidone, etc.
Since the formulation cannot be used due to solidification and decreased effectiveness due to volatilization of the solvent, other solvents or methods are desired. Object of the invention The object of the invention is to dissolve pendimethalin,
It is an object of the present invention to provide a solvent that can be manufactured as a granular agent, and to provide a granular agent that exhibits excellent herbicidal effects without agglomeration or solidification after long-term storage. Structure of the Invention The present invention provides A granular carrier, B (i) pendimethalin, and (ii) the general formula (In the formula, R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 are lower alkyl groups having 1 to 4 carbon atoms.) This is a granular herbicide composition for field use. The components of the present invention will be explained in detail below. (Granular carrier) The granular carrier used in the present invention includes silica sand,
Natural products such as pumice and calcium carbonate, or granulated products may also be used. The particle size is 10 to 250 mesh, preferably 32 to 100 mesh, and preferably contains 95% by weight or more of particles in the range of 32 to 100 mesh. Depending on the purpose, they may be used alone or in combination of two or more. (Pendimetalin) Pendimethalin, which is an agricultural chemical active ingredient used in the present invention, is used in an amount of 0.1 to 10.0% by weight, preferably 0.5 to 5.0% by weight, based on the total amount of the granular herbicide composition. (Compounds represented by the general formula) The compounds represented by the general formula used in the present invention include phenyldimethylphenylethanes, phenyldimethylphenylmethanes, phenyldiethyl phenylethanes, and phenyldipropylphenylethanes. There are enylethanes, phenyldibutyl phenylethanes, etc., such as phenyl 2,3-dimethylphenylethane, phenyl 2,4-dimethylphenylethane, phenyl 2,5-dimethylphenylethane, phenyl 2,6-dimethylphenylethane, phenyl 3,4-dimethylphenylethane, phenyl 3,5-dimethylphenylethane,
Phenyl 2,4-dimethylphenylmethane, phenyl 3,4-dimethylphenylmethane, phenyl 3,5-dimethylphenylmethane, phenyl 3,
5-dibutylphenylethane, phenyl 3,5-
Examples include diisopropylphenylmethane, which may be used alone or in combination of two or more. However, it is not necessarily limited to these exemplified compounds. The compound represented by the general formula used in the present invention may be handled in the same manner as a general solvent. In addition, the amount used is 0.2 to 0.2 of the total amount of the granular herbicide composition.
It may be 10.0% by weight, preferably 0.5-5.0% by weight. (Other additives) In addition, as long as they do not interfere with the present invention, for example, fine powders such as talc, clay, and white carbon, pigments such as red iron, molybdenum blue, and titanium white, colorants such as methylene blue, and rhodamine B, and polyesters. Surfactants such as oxyethylene alkyl phenyl ether sulfate ammonium salt, polyoxyethylene alkyl ether sulfate ammonium salt, and dialkyl sulfosuccinate ester sodium salt can be added as necessary. Further, in the present invention, other agricultural chemicals such as herbicides, insecticides, and fungicides can be added. Effects of the present invention The pendimethalin granular herbicide for field use of the present invention has the following properties: (1) Since the active ingredient diffuses well in the field soil, the herbicidal effect can be uniformized and improved. (2) No agglomeration or solidification is observed when the product is stored for a long period of time, and the physicochemical properties required for a granulating agent are good. (3) Since there are no problems with solvent volatility, odor, etc., there is no need to pay special attention to the dangers of the solvent during production, which is advantageous. It has excellent aspects such as: Examples Next, Examples and Test Examples of the present invention will be given and specifically explained, but the Examples are not intended to limit the present invention in any way. In addition, the parts or percentages shown below are:
Represents parts by weight or weight %. Example 1 96 parts of granular pumice sieved into 32 to 100 meshes were placed in a mixer, and a solution prepared by heating and dissolving 1 part of pendimethalin drug substance in 3 parts of phenyl 3,4-dimethylphenylethane was added to the mixer. Add 15
Mixed for a minute to obtain granules containing 1% pendimethalin. Example 2 96 parts of the granular carrier used in Example 1 were placed in a mixer, and a solution prepared by heating and dissolving 2 parts of pendimethalin drug substance in 2 parts of phenyl 3,5-dimethylphenylethane was added thereto. and mix for 15 minutes,
Granules containing 2% pendimethalin were obtained. Example 3 93 parts of the granular carrier used in Example 1 were placed in a mixer, and a solution prepared by heating and dissolving 4 parts of pendimethalin drug substance in 3 parts of phenyl 3,5-diethyl phenylethane was added thereto. and mix for 15 minutes,
Granules containing 4% pendimethalin were obtained. Example 4 95 parts of the granular carrier used in Example 1 were placed in a mixer, and a solution prepared by heating and dissolving 2 parts of pendimethalin drug substance in 3 parts of phenyl 3,5-diisopropylphenylethane was added thereto. and mixed for 15 minutes to obtain granules containing 2% pendimethalin. Example 5 94 parts of the granular carrier used in Example 1 were placed in a mixer, and a mixture of 2 parts of phenyl 3,4-dimethylphenylethane and 2 parts of phenyl 3,5-dimethylphenylmethane was added to the mixer. A solution prepared by heating and dissolving 2 parts of deimetalin drug substance in advance was added and mixed for 15 minutes to obtain granules containing 2% pendimethalin. Example 6 94 parts of granular silica sand sieved to a size of 32 to 100 mesh was placed in a mixer, and 2 parts of phenyl 3,5-dibutyl phenylethane and 2 parts of pendimethalin were added.
Add 2 parts of white carbon and mix for another 15 minutes.
A granule containing the following was obtained. Comparative Example 1 95 parts of the granular carrier used in Example 1 were placed in a mixer, and a solution obtained by heating and mixing 4 parts of polyethylene glycol (average molecular weight 400) and 1 part of pendimethalin drug substance was poured into the mixer, and 15 parts of the granular carrier used in Example 1 was added. Mixed for a minute. However, it could not be adsorbed uniformly and the particles formed into aggregates. Therefore, it was not possible to formulate the product in this example. Comparative Example 2 95 parts of the granular carrier used in Example 1 were placed in a mixer, and a solution prepared by heating and dissolving 1 part of pendimethalin in 3 parts of N-methyl-2-pyrrolidone was added thereto, and the mixture was heated for 15 minutes. The mixture was mixed to obtain granules containing 1% pendimethalin. Comparative Example 3 95 parts of the granular carrier used in Example 1 were placed in a mixer, and a solution prepared by heating and dissolving 2 parts of pendimethalin drug substance in 3 parts of xylene was added thereto.
Mixed for 15 minutes to obtain granules containing 2% pendimethalin. Comparative Example 4 94 parts of the granular carrier used in Example 1 were placed in a mixer, and a solution prepared by heating and dissolving 4 parts of pendimethalin drug substance in 2 parts of N-methyl-2-pyrrolidone was added thereto. Mixed for 15 minutes to obtain granules containing 4% pendimethalin. Comparative Example 5 95.5 parts of the granular carrier used in Example 1 was placed in a mixer, and 2 parts of pendimethalin raw material was added to a mixture of 0.5 parts of N-methyl-2-pyrrolidone and 2 parts of soybean oil.
Pour a solution that has been heated and dissolved in advance, and add 15
Mixed for a minute to obtain granules containing 2% pendimethalin. Comparative Example 6 94 parts of the granular carrier used in Example 5 were placed in a mixer, and a solution prepared by heating and dissolving 2 parts of pendimethalin drug substance in 2 parts of cyclohexanone was added thereto, mixed for 15 minutes, and then , 2 parts of white carbon were added and further mixed for 15 minutes to obtain granules containing 2% pendimethalin. Test Example 1 [Solidification test after pressurized storage] 20 g of the pendimethalin granules produced in Examples 1 to 6 and Comparative Examples 2 to 6 were placed in a glass cylindrical container (bottomless) with an inner diameter of 6.0 to 6.5 cm, and 25 g Place a steel weight and pressurize it so that the amount is / cm 2 . This is room temperature and 50℃
After 1 and 5 days, remove the cylindrical container and observe the solidification state. Table 1 shows the results determined based on the following criteria. Judgment Criteria -: Good fluidity without agglomeration. +: Agglomeration is observed in some parts. ≠: Agglomeration is observed throughout and fluidity is lost.
【表】
試験例 ２
〔土壌拡散試験〕
11×11cmのポツトを使用し、底部から２cmの深
さになるように砂を入れ、その上に畑土壌を10cm
入れ、さらに、メヒシバまたはオオイヌタデの種
子を混播した畑土壌を1.5cm入れた。土壌水分は
15％で管理した。このように作製したポツトの中
心部に各製剤を50mg処理し、30日目に円形状に発
現した生育抑制効果（０：影響なし１〜５：完全
枯死）の4.5以上の部分の直径を測定することに
より拡散率で数値化した。そして、比較例５の粒
状剤の直径を拡散率100とし、各製剤の拡散率を
第２表および第３表に示す。[Table] Test example 2 [Soil diffusion test] Use an 11 x 11 cm pot, fill it with sand to a depth of 2 cm from the bottom, and add 10 cm of field soil on top of it.
Then, 1.5 cm of field soil mixed with seeds of crabgrass or Japanese knotweed was added. Soil moisture is
Managed at 15%. 50 mg of each preparation was applied to the center of the pots prepared in this way, and on the 30th day, the diameter of the circular growth-inhibiting effect (0: no effect, 1 to 5: complete death) of 4.5 or more was measured. By doing this, the diffusion rate was quantified. The diameter of the granule of Comparative Example 5 was set as a diffusivity of 100, and the diffusivity of each formulation is shown in Tables 2 and 3.
【表】【table】
【表】【table】
【表】
以上の結果により、本発明の粒状剤は比較例の
粒状剤と比べて、拡散性が優れていることが判
る。
試験例 ３
〔除草効果試験〕
試験例２で用いた畑土壌ポツトを土壌水分15％
に管理し、表面に有効成分量として１mgになる量
の各製剤を均一に散布した。処理後30日目に各雑
草への生育抑制効果を観察した。次の判定基準に
より判定した結果を第４表および第５表に示す。
判定基準
０：影響なし
〓
100：完全枯死[Table] From the above results, it can be seen that the granular agent of the present invention has excellent diffusibility compared to the granular agent of the comparative example. Test Example 3 [Herbicidal Effect Test] The field soil pot used in Test Example 2 was placed at a soil moisture level of 15%.
Each preparation was uniformly sprayed on the surface in an amount of 1 mg of active ingredient. The growth inhibitory effect on each weed was observed 30 days after treatment. Tables 4 and 5 show the results determined based on the following criteria. Judgment criteria 0: No effect 100: Completely dead
【表】【table】
【表】
以上の結果により、本発明の粒状剤は、比較例
の粒状剤と比べて除草光果が優れていることが判
る。[Table] From the above results, it can be seen that the granular agent of the present invention is superior in herbicidal light compared to the granular agent of the comparative example.
Claims (1)
チル−２，６−ジニトロアニリンおよび (ii) 一般式 （式中R1は水素原子またはメチル基、R2お
よびR3は炭素数１〜４個の低級アルキル基
である） で示される１種または２種以上の化合物を担持さ
せてなることを特徴とする畑作用粒状除草剤組成
物。 ２ 粒状担体が32〜100メツシユの範囲のものを
95重量％以上含有することを特徴とする特許請求
の範囲第１項記載の畑作用粒状除草剤組成物。 ３ Ｎ−（１−エチルプロピル）−３，４−ジメチ
ル−２，６−ジニトロアニリンを粒状除草剤組成
物全量の0.1〜10.0重量％担持させることを特徴
とする特許請求の範囲第１項記載の畑作用粒状除
草剤組成物。 ４ 一般式で示される１種又は２種以上の化合
物を粒状除草剤組成物全量の0.2〜10.0重量％担
持させることを特徴とする特許請求の範囲第１項
記載の畑作用粒状除草剤組成物。[Scope of Claims] 1 A granular carrier, B (i) N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline and (ii) the general formula (In the formula, R 1 is a hydrogen atom or a methyl group, and R 2 and R 3 are lower alkyl groups having 1 to 4 carbon atoms.) A granular herbicide composition for field use. 2 The granular carrier has a size of 32 to 100 mesh.
The granular herbicide composition for field use according to claim 1, characterized in that the composition contains 95% by weight or more. 3 N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline is supported in an amount of 0.1 to 10.0% by weight based on the total amount of the granular herbicide composition. A granular herbicide composition for field use. 4. The granular herbicide composition for field use according to claim 1, characterized in that one or more compounds represented by the general formula are carried in an amount of 0.2 to 10.0% by weight based on the total amount of the granular herbicide composition. .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9881484A JPS60243001A (en) | 1984-05-18 | 1984-05-18 | Granular herbicidal composition for upland farming |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9881484A JPS60243001A (en) | 1984-05-18 | 1984-05-18 | Granular herbicidal composition for upland farming |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60243001A JPS60243001A (en) | 1985-12-03 |
| JPH0430361B2 true JPH0430361B2 (en) | 1992-05-21 |
Family
ID=14229790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9881484A Granted JPS60243001A (en) | 1984-05-18 | 1984-05-18 | Granular herbicidal composition for upland farming |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60243001A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986004214A1 (en) * | 1985-01-24 | 1986-07-31 | Takeda Chemical Industries, Ltd. | Agricultural chemical preparation having alleviated toxicity against fish |
| JPH0639362B2 (en) * | 1985-07-29 | 1994-05-25 | 住友化学工業株式会社 | Agrochemical solid formulation |
| JP2551775B2 (en) * | 1986-05-19 | 1996-11-06 | 武田薬品工業株式会社 | Agrochemical solid formulation |
| JPH07106961B2 (en) * | 1986-08-06 | 1995-11-15 | 日本農薬株式会社 | Improved agricultural granules and fine granules |
-
1984
- 1984-05-18 JP JP9881484A patent/JPS60243001A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60243001A (en) | 1985-12-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0430361B2 (en) | ||
| JPH02288803A (en) | Granule for paddy field herbicide having sustained release | |
| JP2813213B2 (en) | Granular wettable powder composition | |
| JPS60214701A (en) | Suspended agricultural chemical composition | |
| JPS5828841B2 (en) | Pesticide granules for water surface application | |
| KR100203760B1 (en) | Herbicide granule with sustained release for paddy rice | |
| JPS58148879A (en) | Pyrazolsulfonylurea derivative, its preparation, and herbicide containing it | |
| JPH05262608A (en) | Herbicide composition | |
| JP2567926B2 (en) | Anti-solidification agent for agricultural chemicals and non-solidifying pesticide granules containing the anti-solidification agent | |
| JPH068242B2 (en) | Improved paddy herbicide composition | |
| JPS62138404A (en) | Herbicide | |
| JPS62126102A (en) | Granular herbicide composition for field use | |
| JPS62145003A (en) | Herbicidal composition | |
| JP5989915B2 (en) | 粉 Pest control powder | |
| JP2516015B2 (en) | Agro-horticultural wettable powder composition | |
| CN104585173A (en) | Production technology of weedicide | |
| JPS5839656A (en) | Phenylurea derivative and selective herbicide | |
| JPS6212761A (en) | Tetrahydroindazole derivative, production thereof and herbicide containing said derivative as active constituent | |
| CN112219857A (en) | Cyhalothrin aqueous emulsion and low-energy emulsification preparation method thereof | |
| JPS5872502A (en) | Herbicidal composition | |
| JPH0515682B2 (en) | ||
| JPS5859973A (en) | Pyridazinone derivative and its preparation | |
| JPS58144384A (en) | Cyclohexane derivatives, their production methods and herbicides | |
| JPS5813505A (en) | Herbicidal composition | |
| JPS623835B2 (en) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |