JPH0433762B2 - - Google Patents
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- Publication number
- JPH0433762B2 JPH0433762B2 JP60130760A JP13076085A JPH0433762B2 JP H0433762 B2 JPH0433762 B2 JP H0433762B2 JP 60130760 A JP60130760 A JP 60130760A JP 13076085 A JP13076085 A JP 13076085A JP H0433762 B2 JPH0433762 B2 JP H0433762B2
- Authority
- JP
- Japan
- Prior art keywords
- salt
- substance
- compound
- composition
- test
- 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 - Lifetime
Links
- 230000002363 herbicidal effect Effects 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 23
- RTWIRLHWLMNVCC-WQYNNSOESA-M sodium (2S)-2-[[(2S)-2-[[(2S)-2-amino-4-[hydroxy(methyl)phosphoryl]butanoyl]amino]propanoyl]amino]propanoate Chemical compound [Na+].[O-]C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O RTWIRLHWLMNVCC-WQYNNSOESA-M 0.000 claims description 22
- 239000004009 herbicide Substances 0.000 claims description 18
- 239000003945 anionic surfactant Substances 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 9
- 239000002736 nonionic surfactant Substances 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 239000010452 phosphate Substances 0.000 claims description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 241000196324 Embryophyta Species 0.000 description 27
- 235000002639 sodium chloride Nutrition 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- -1 alkali metal salts Chemical class 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 9
- 235000021317 phosphate Nutrition 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- 240000003176 Digitaria ciliaris Species 0.000 description 3
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000008378 aryl ethers Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 208000032484 Accidental exposure to product Diseases 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 244000245600 Persicaria longiseta Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000001341 Reynoutria japonica Species 0.000 description 1
- 235000018167 Reynoutria japonica Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- QNICMVJKCYAMIK-UHFFFAOYSA-L disodium octadecanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O QNICMVJKCYAMIK-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000011890 leaf development Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- RCMHUQGSSVZPDG-UHFFFAOYSA-N phenoxybenzene;phosphoric acid Chemical compound OP(O)(O)=O.C=1C=CC=CC=1OC1=CC=CC=C1 RCMHUQGSSVZPDG-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
（産業上の利用分野）
本発明は殺草性化合物SF−1293物質の殺草効
果が増強された殺草剤組成物に関する。
更に詳しくは、下記の式〔〕
で表わされる除草性SF−1293物質（特公昭59−
23282号）またその塩の殺草効力を著るしく増大
せしめた殺草剤組成物に関する。
（従来の技術及び解決すべき問題点）
前記の式〔〕のSF−1293物質及びその塩類
（たとえば、アルカリ金属塩、アルカリ土類金属
塩、アンモニウム塩、有機アミン塩、等）は、一
年生雑草及び多年生雑草に対して極めて強い殺草
力を有することが知られている（特公昭59−
23282号及び米国特許第4309208号参照）。従つて、
たとえばSF−1293物質又はその塩は屋敷内、テ
ニスコート、バレーコート、サツカー場、あるい
は工場敷地、鉄道線路、山林原野、農耕地、果樹
園、などで除草剤として広く使用し得るものであ
る。
しかしながら、式〔〕の化合物又はその塩の
単独のみでは、各種雑草の葉面への付着性、湿展
性あるいは固着性等が不充分であるため、あるい
は風雨等によつて脱落もしくは流亡するなどの原
因でSF−1293物質本来の強い殺草力を発揮でき
ない場合も多いために、多量の薬剤を使用するこ
とが必要であつた。
除草剤を使用するに際しては、界面活性剤を加
用することが一般的である。しかしながら界面活
性剤を加用しても全く除草剤の効果が変化しない
場合、加用することによつて除草剤の効果が劣化
される場合、界面活性剤が除草成分の分解を助長
する場合等が知られている。従つて、特定の除草
剤化合物成分、界面活性剤および除草対象植物の
組み合わせを適当に選定することによつて、初め
て好ましい除草効力の増加が得られる場合がある
と考えるのが従来の通念である〔杉村等，「植物
の化学調節」19巻No.１，34〜49頁（1984年）及び
J.B.WYRILI，O.C.BURNSIDE
「WEEDSCIENCE」25巻，３版，（1977）〕。
従つて、除草性化合物成分を効果的に利用すべ
きであるという見地に立てば、除草剤を使用する
に際して、上記したような好ましい配合成分の組
み合わせを見出すことなしに単に無計画に界面活
性剤の加用をすることは避けることが望ましい。
このような技術的背景を理解すれば、実用され
る新規な除草剤を提供するに際しては、除草の目
的を有効に達成するための選定された適切な配合
製剤を見出すことは、極めて重要な課題である。
そこで本発明者らは、式〔〕のSF−1293化
合物又はその塩に第４級アンモニウム塩および非
イオン性界面活性剤を配合することにより、除草
効果の強い溶液型のSF−1293物質製剤を得るこ
とを見出して既に提案した（特開昭60−4112号）。
しかしながら、上記の溶液型製剤を製造するに
当つては、式〔〕の化合物又はその塩を多量に
配合することが必要であり、必らずしも満足でき
るものでなはなく、更に除草効果が強力かつ効率
の良い改良された殺草剤組成物を見出すことが必
要であつた。また、前記特開昭60−4112号の発明
に係る組成物は溶液製剤の形しか製造することが
出来ないので、別途、式〔〕の化合物又はその
塩の特長を活かし且つ便利に使用できて誤飲の危
険性を防止された水溶剤等の水溶性固体製剤の形
で製造できる特性を有するSF−1293物質組成物
を求める強い要求があつた。
（問題点を解決するための手段）
そこで本発明者等は式〔〕の化合物又はその
塩である殺草性化合物の配合割合及び実用使用量
を減量しても強い殺草効果を有するSF−1293物
質含有の殺草性組成物を得るために、式〔〕の
化合物又はその塩と、各種の界面活性剤および／
あるいは他の広範な補助剤との適切な組み合わ
せ、ならびに適切な配合割合を具体的に知見すべ
く、また水溶剤等の水溶性固体製剤の形に調製で
きる特性を付与することを目的として鋭意研究を
行つた。
その結果、後記する特定のサルフエート系、ス
ルホネート系ホスフエート系、およびカルボン酸
系陰イオン性界面活性剤がその単用でも、その混
用でも、或る選定された配合割合の範囲内で、式
〔〕の化合物又はその塩（以下、単に(a)成分と
いうこともある）と併用されると、後者の除草性
化合物の植物体内への吸収移行を顕著に増加せし
めること従つて殺草効果も増強できることを発見
した。従つて本発明はこのような余人の想起し得
ない、式〔〕の化合物およびその塩の特性の新
たな発見に基づくものである。
更に本発明者らは、前記の特定のサルフエート
系、スルホネート系、ホスフエート系およびカル
ボン酸系陰イオン性界面活性剤の１種または２種
以上（以下、単に(b)成分ということもある）と、
ポリオキシアルキレン系非イオン性界面活性剤の
１種または２種以上（以下、(c)成分ということも
ある）とを、或る選定された、特定の配合割合で
式〔〕の化合物又はその塩に対して配合するこ
とにより、著るしく殺草効果が増大されたSF−
1293物質含有組成物が作成できることを見出し
た。
加えて、これらの(a)成分、(b)成分の２者、また
は(a)成分、(b)成分、(c)成分の３者の特定な配合割
合を用い且つその他の適切な補助剤およびまたは
担体を選定し、しかも通常の製剤技術を用いるこ
とによつて、もう一つの課題であつた水溶剤等の
水溶性固体製剤の形で調製できるという特性の付
与することに成功し、これらの知見に基づいて、
本発明を完成した。
従つて、第１の本発明の要旨とするところは、
(a)SF−1293物質又はその塩と、(b)サルフエート
系、スルホネート系、ホスフエート系又はカルボ
ン酸系陰イオン性界面活性剤の１種又は２種以上
とを、(a)：(b)の割合（重量比）が１：0.5〜１：
20の範囲で含有することを特徴とする殺草剤組成
物にある。
また、第２の本発明の要旨とするところは、(a)
SF−1293物質又はその塩と、(b)サルフエート系、
スルホネート系、ホスフエート系又はカルボン酸
系陰イオン性界面活性剤の１種又は２種以上と、
(c)ポリオキシアルキレン系非イオン性界面活性剤
の１種または２種以上とを、(a)：(b)の割合（重量
比）が１：0.5〜１：20の範囲で且つ(a)：(c)の割
合（重量比）が１：0.1〜１：20の範囲で含有す
ることを特徴とする殺草剤組成物にある。
本発明に用いられる(b)成分の陰イオン性界面活
性剤の例としては、下記のものがある。
（） サルフエート系界面活性剤
アルキル（炭素数８〜22）サルフエート。
ポリオキシアルキレンアルキル（炭素数８〜22）
エーテルサルフエート。
ポリオキシアルキレンアルキル（炭素数４〜11）
アリールエーテルサルフエート。
ポリオキシアルキレンスチレン化フエノールエー
テルサルフエート。
（）スルホネート系界面活性剤
アルキル（炭素数４〜16）ベンゼンスルホネー
ト。
ジアルキルスルホコハク酸塩。
アルキル（炭素数４〜16）ジフエニエルエーテ
ルスルホネート。
α−オレフイン（炭素数８〜22）スルホネー
ト。
（）ホスフエート系界面活性剤
アルキル（炭素数８〜22）ホスフエート。
ポリオキシアルキレンアルキル（炭素数８〜
22）
ホスフエート。
ポリオキシアルキレンアルキル（炭素数４〜
16）
フエニルエーテルホスフエート。
（）カルボン系界面活性剤
オレイン酸カリウム
半硬化牛脂肪酸カリウム
ステアリン酸ナトリウム
混合脂肪酸ナトリウム
上記のうちでも、アルキルサルフエート、ポリ
オキシアルキレンアルキルサルフエート、アルキ
ルホスフエート、ポリオキシエチレンアルキルホ
スフエートが好ましい。
これらの界面活性剤は単独でも２種以上の併用
であつてもよい。
第１又は第２の本発明に係る組成物において、
陰イオン性界面活性剤(b)の配合割合は、式〔〕
の化合物又はその塩(a)に対し(a)：(b)の重量比で
１：0.5〜１：20の範囲、好ましくは１：0.5〜
１：10の範囲である。
第２の本発明の組成物においては、式〔〕の
化合物またはその塩(a)と陰イオン性界面活性剤(b)
との他に、ポリオキシアルキレン系非イオン性界
面活性剤の１種又は２種以上(c)が配合されてお
り、前述の優れた効果が得られる。
第２の本発明の組成物における(c)成分としての
ポリオキシアルキレン系非イオン性界面活性剤の
例には、下記のものがある。
ポリオキシアルキレンアルキル（炭素数８〜
22）エーテル。
ポリオキシアルキレンアルキル（炭素数４〜
16）アリールエーテル。
ポリオキシアルキレンアリールエーテル。
ポリオキシアルキレンアルキル（炭素数８〜
22）エステル。
ポリオキシアルキレンアルキル（炭素数８〜
22）ソルビタンエステル。
ポリオキシアルキレンアルキル（炭素数８〜
22）ソルビトールエステル。
ポリオキシアルキレンアルキル（炭素数８〜
22）グリセロールエステル。
ポリオキシアルキレンブロツク重合体。
ポリオキシアルキレンブロツク重合体アルキル
グリセロールエステル。
ポリオキシアルキレン系非イオン性界面活性剤
(c)の配合割合は式〔〕の化合物又はその塩(a)に
対し(a)：(c)の重量比で１：0.1〜１：20の範囲、
好ましくは１：0.5〜１：10の範囲である。
更に、第２の本発明組成物中では、(b)陰イオン
性界面活性剤と(c)ポリオキシアルキレン系非イオ
ン性界面活性剤の割合は、(b)：(c)の重量比で１：
４〜１：0.25の範囲が好ましく、より好ましくは
１：３〜１：0.33の範囲である
本発明の殺草剤組成物は、液剤の形のみなら
ず、水溶剤、すなわち粉末形、顆粒形、等の水溶
性固体製剤としても調製でき、更に懸濁剤、水和
剤であつてもよい。
水溶剤では、増量剤として芒硝、硫安、食塩な
どの塩の如き水溶性無機物質や、糖類、尿素など
の水溶性有機物質が配合できる。
その他、本発明の作用効果を害しない範囲で製
剤設計を考慮して、通常の任意の添加成分を配合
することが出来る。
（発明の効果）
上記、記述のごとく、本発明の殺草剤組成物
は、式〔〕の化合物又はその塩(a)の殺草効果
を、以下の実施例及び試験例で述べる通り増強さ
せると共に、従来調製できなかつた水溶剤等の水
溶性固体製剤の形での製造を可能ならしめた利点
がある。しかも、このような水溶性固体製剤とし
て調製された本発明組成物においては、式〔〕
の化合物又はその塩は、その経時安定性が液剤の
場合に比べて非常に向上されるという予想外の利
点をもつことも知見された。
更に、本発明の組成物は、茎葉散布後に降雨が
あつて流亡、殺草効力を低下する恐れが防止され
るという耐雨性が改善される利点もある。
なお、本発明の殺草剤組成物は１年生雑草はも
ちろんのこと、シバムギ、ギヨウギシバ、カヤツ
リグサなどの多年生雑草の除草にも有効である。
以下、本発明の組成物の有用性を試験例および
実施例により説明する。
試験例１ 植物体吸収移行性試験
SF−1293物質のナトリウム塩と、第１表に示
した界面活性剤とを、それぞれ100μｇ／ml又は
150μｇ／mlづつ含有する水溶液を調製して供試
薬液とした。供試植物としては３号素焼鉢に３本
づつ育苗した第１本葉展開初期のキユウリ苗（品
種：ときわ地這）を用いた。
試験は次の通りに行つた。すなわち、供試植物
の子葉の一方の葉上に供試薬液をマイクロピペツ
トを用いて１葉あたり50μ宛を滴下して施用し
た。４日後に、薬液を施用しなかつた残りの子葉
および本葉を採取し、細切後80％メタノールで加
温抽出して分析用試料を得、バチルス・ズブチル
ス（Bacillus subtilus）ATCC6633を被験菌とす
る生物検定によつて、試料を投与しなかつた植物
部位へのSF−1293物質Na塩として吸収移行量
（分析試料として用いた試料植物の乾燥重量中の
SF−1293物質Na塩の量）を定量した、供試植物
は１処理区につき30本を使用した。
吸収移行率（％）は、SF−1293物質ナトリウ
ム塩水溶液のみを用いた試験を対照として、百分
率で次式で計算した。
吸収移行率(%)＝処理区の試料植物乾物重1g当りのSF
−1293物質Na塩の移行μｇ数／対照区の試料植物乾物重
1g当りのSF−1293物質Na塩の移行μｇ数×100
得られた結果は、第１表に示す通りである。
(Industrial Application Field) The present invention relates to a herbicide composition in which the herbicidal effect of the herbicidal compound SF-1293 is enhanced. For more details, use the following formula [] Herbicidal SF-1293 substance expressed by
No. 23282) It also relates to a herbicide composition in which the herbicidal efficacy of the salt is significantly increased. (Prior art and problems to be solved) The SF-1293 substance of formula [] and its salts (e.g., alkali metal salts, alkaline earth metal salts, ammonium salts, organic amine salts, etc.) are used to treat annual weeds. It is known to have extremely strong herbicidal power against perennial weeds and perennial weeds.
23282 and U.S. Pat. No. 4,309,208). Therefore,
For example, the SF-1293 substance or its salt can be widely used as a herbicide in mansions, tennis courts, volleyball courts, soccer fields, factory grounds, railroad tracks, forests, fields, agricultural fields, orchards, etc. However, when the compound of formula [] or its salt alone is used alone, it has insufficient adhesion, wet spreadability, or adhesion to the leaves of various weeds, or it may fall off or be washed away by wind and rain. In many cases, the SF-1293 substance is unable to exert its inherent strong herbicidal power due to the above reasons, so it has been necessary to use large amounts of the chemical. When using herbicides, it is common to add a surfactant. However, there are cases where the effect of the herbicide does not change at all even if a surfactant is added, cases where the effect of the herbicide is deteriorated by adding the surfactant, cases where the surfactant promotes the decomposition of the herbicide component, etc. It has been known. Therefore, it is conventional wisdom that a desirable increase in herbicidal efficacy may be obtained only by appropriately selecting a combination of specific herbicide compound components, surfactants, and plants to be weeded. [Sugimura et al., "Chemical Regulation of Plants" Vol. 19 No. 1, pp. 34-49 (1984) and
JBWYRILI，OCBURNSIDE
“WEEDSCIENCE” Volume 25, 3rd edition, (1977)]. Therefore, from the standpoint that herbicidal compound components should be used effectively, when using herbicides, surfactants are simply added haphazardly without finding the preferred combination of ingredients as described above. It is desirable to avoid adding Understanding this technical background, when providing a new herbicide for practical use, it is extremely important to find an appropriate combination formulation to effectively achieve the purpose of weed control. It is. Therefore, the present inventors created a solution-type SF-1293 substance preparation with a strong herbicidal effect by blending the SF-1293 compound of formula [] or its salt with a quaternary ammonium salt and a nonionic surfactant. I have already proposed this method after discovering the benefits (Japanese Patent Application Laid-Open No. 60-4112). However, in producing the above solution-type preparation, it is necessary to incorporate a large amount of the compound of formula [] or its salt, which is not always satisfactory, and also has a herbicidal effect. There was a need to find improved herbicide compositions that were more potent and efficient. Furthermore, since the composition according to the invention of JP-A No. 60-4112 can only be produced in the form of a solution, it is possible to use the compound of formula [] or its salt separately and conveniently by taking advantage of its characteristics. There has been a strong need for compositions of SF-1293 substances that have the properties to be manufactured in the form of water-soluble solid formulations, such as water-based solutions, which prevent the risk of accidental ingestion. (Means for Solving the Problems) Therefore, the present inventors have discovered that SF-3, which has a strong herbicidal effect even if the blending ratio and practical usage amount of the herbicidal compound, which is the compound of formula [] or its salt, is reduced. In order to obtain a herbicidal composition containing the 1293 substance, a compound of formula [] or a salt thereof, various surfactants and/or
In addition, we are conducting intensive research with the aim of specifically finding out the appropriate combination with a wide range of other adjuvants, as well as the appropriate blending ratio, as well as imparting properties that allow preparation in the form of water-soluble solid preparations such as water solvents. I went there. As a result, whether the specific sulfate-based, sulfonate-based phosphate, or carboxylic acid-based anionic surfactants described later are used alone or in combination, within a certain selected blending ratio, the formula [] When used in combination with the compound or its salt (hereinafter sometimes simply referred to as component (a)), the absorption and transfer of the latter herbicidal compound into the plant body can be significantly increased, and the herbicidal effect can therefore also be enhanced. discovered. Therefore, the present invention is based on the new discovery of the properties of the compound of formula [] and its salts, which have never occurred to anyone else. Furthermore, the present inventors have discovered that one or more of the above-mentioned specific sulfate-based, sulfonate-based, phosphate-based, and carboxylic acid-based anionic surfactants (hereinafter sometimes simply referred to as component (b)) ,
One or more polyoxyalkylene nonionic surfactants (hereinafter also referred to as component (c)) are mixed with a compound of formula [] or its compound in a selected specific blending ratio. SF- whose herbicidal effect was significantly increased by adding it to salt
It has been discovered that a composition containing 1293 substances can be created. In addition, using a specific blending ratio of two of these components (a), (b), or three of components (a), (b), and (c), and using other appropriate adjuvants. By selecting and/or carriers and using ordinary formulation techniques, we succeeded in imparting the property of being able to prepare water-soluble solid preparations, which was another problem, and these Based on the knowledge of
The invention has been completed. Therefore, the gist of the first invention is as follows:
(a) SF-1293 substance or its salt; (b) one or more sulfate-based, sulfonate-based, phosphate-based, or carboxylic acid-based anionic surfactants; (a):(b) The ratio (weight ratio) is 1:0.5 to 1:
20. Furthermore, the gist of the second invention is (a)
SF-1293 substance or its salt, (b) sulfate type,
One or more sulfonate-based, phosphate-based, or carboxylic acid-based anionic surfactants;
(c) one or more polyoxyalkylene nonionic surfactants in a ratio (weight ratio) of (a):(b) in the range of 1:0.5 to 1:20; ):(c) (weight ratio) in a range of 1:0.1 to 1:20. Examples of the anionic surfactant as component (b) used in the present invention include the following. () Sulfate surfactant Alkyl (8 to 22 carbon atoms) sulfate. Polyoxyalkylene alkyl (8 to 22 carbon atoms) ether sulfate. Polyoxyalkylene alkyl (4 to 11 carbon atoms) aryl ether sulfate. Polyoxyalkylene styrenated phenol ether sulfate. () Sulfonate surfactant Alkyl (4 to 16 carbon atoms) benzene sulfonate. Dialkyl sulfosuccinate. Alkyl (4-16 carbon atoms) diphenyl ether sulfonate. α-olefin (8 to 22 carbon atoms) sulfonate. () Phosphate surfactant Alkyl (8 to 22 carbon atoms) phosphate. Polyoxyalkylene alkyl (8 or more carbon atoms)
22) Phosphates. Polyoxyalkylene alkyl (carbon number 4~
16) Phenyl ether phosphate. () Carboxylic surfactant Potassium oleate Potassium semi-hardened beef fatty acid Sodium stearate Sodium of mixed fatty acids Among the above, alkyl sulfates, polyoxyalkylene alkyl sulfates, alkyl phosphates, and polyoxyethylene alkyl phosphates are preferred. These surfactants may be used alone or in combination of two or more. In the composition according to the first or second invention,
The blending ratio of anionic surfactant (b) is determined by the formula []
The weight ratio of (a):(b) to the compound or its salt (a) is in the range of 1:0.5 to 1:20, preferably 1:0.5 to
The range is 1:10. In the second composition of the present invention, a compound of formula [] or a salt thereof (a) and an anionic surfactant (b)
In addition to this, one or more polyoxyalkylene nonionic surfactants (c) are blended, and the above-mentioned excellent effects can be obtained. Examples of the polyoxyalkylene nonionic surfactant as component (c) in the composition of the second invention include the following. Polyoxyalkylene alkyl (8 or more carbon atoms)
22) Ether. Polyoxyalkylene alkyl (carbon number 4~
16) Aryl ether. Polyoxyalkylene aryl ether. Polyoxyalkylene alkyl (8 or more carbon atoms)
22) Esther. Polyoxyalkylene alkyl (8 or more carbon atoms)
22) Sorbitan ester. Polyoxyalkylene alkyl (8 or more carbon atoms)
22) Sorbitol ester. Polyoxyalkylene alkyl (8 or more carbon atoms)
22) Glycerol ester. Polyoxyalkylene block polymer. Polyoxyalkylene block polymer alkylglycerol ester. Polyoxyalkylene nonionic surfactant
The blending ratio of (c) is in the range of 1:0.1 to 1:20 in weight ratio of (a):(c) to the compound of formula [] or its salt (a),
Preferably it is in the range of 1:0.5 to 1:10. Furthermore, in the second composition of the present invention, the proportion of (b) anionic surfactant and (c) polyoxyalkylene nonionic surfactant is a weight ratio of (b):(c). 1:
The herbicide composition of the present invention is preferably in the range of 4 to 1:0.25, more preferably in the range of 1:3 to 1:0.33. It can also be prepared as a water-soluble solid preparation such as , etc., and may also be a suspension or a wettable powder. In the case of an aqueous solvent, water-soluble inorganic substances such as salts such as mirabilite, ammonium sulfate, and common salt, and water-soluble organic substances such as sugars and urea can be added as fillers. In addition, any conventional additive components can be added in consideration of formulation design within a range that does not impair the effects of the present invention. (Effect of the invention) As described above, the herbicide composition of the present invention enhances the herbicidal effect of the compound of formula [] or its salt (a) as described in the following Examples and Test Examples. In addition, there is an advantage in that it enables production in the form of water-soluble solid preparations such as water-soluble ones, which could not be prepared conventionally. Moreover, in the composition of the present invention prepared as such a water-soluble solid preparation, the formula []
It has also been found that the compound or its salt has the unexpected advantage that its stability over time is greatly improved compared to that of a liquid formulation. Furthermore, the composition of the present invention also has the advantage of improved rain resistance, which prevents the risk of washing away and reducing herbicidal efficacy due to rain after spraying on foliage. The herbicide composition of the present invention is effective for weeding not only annual weeds but also perennial weeds such as grasshopper, cyperus, and cyperus. The usefulness of the composition of the present invention will be explained below using Test Examples and Examples. Test Example 1 Plant Absorption and Transfer Test The sodium salt of SF-1293 substance and the surfactant shown in Table 1 were mixed at 100 μg/ml or 100 μg/ml, respectively.
Aqueous solutions each containing 150 μg/ml were prepared and used as test drug solutions. The test plants used were cucumber seedlings (variety: Tokiwa Jiho) in the early stage of the first true leaf development, which were grown in three seedlings each in No. 3 clay pots. The test was conducted as follows. That is, the test chemical solution was applied dropwise onto one of the cotyledons of the test plant using a micropipette in an amount of 50 microns per leaf. After 4 days, the remaining cotyledons and true leaves that were not treated with the chemical solution were collected, cut into small pieces, and then heated and extracted with 80% methanol to obtain samples for analysis. A bioassay was conducted to determine the amount of SF-1293 substance absorbed and transferred as Na salt (in the dry weight of the sample plant used as the analysis sample) to the plant parts to which the sample was not administered.
The amount of SF-1293 substance Na salt) was quantified, and 30 test plants were used in each treatment area. The absorption transfer rate (%) was calculated as a percentage using the following formula using a test using only an aqueous sodium salt solution of SF-1293 substance as a control. Absorption transfer rate (%) = SF per 1g dry weight of sample plants in treated area
−1293 Number of transferred μg of substance Na salt/dry weight of sample plants in control plot
Number of micrograms of SF-1293 substance Na salt transferred per gram x 100 The results obtained are shown in Table 1.
【表】【table】
【表】【table】
【表】
第１表の結果で明らかなように、用いた陰イオ
ン性界面活性剤はSF−1293物質またはその塩の
植物吸収移行を対照試験に比べ、著るしく促進し
た。比較例と比較しても、格段に優れていること
が明らかである。なお陰イオン性界面活性剤のみ
を施用した場合には、供試植物への薬害作用は認
められなかつた。
実施例 １〜86
後記の第２表に示された各成分を、夫々に第２
表に示された配合割合（重量％）になるような量
で均一に混合して混合物を作つた。担体として水
を用いた場合は、この混合物はシフロツプ様溶液
の形の組成物となつた。他方、担体として水以外
の物質（芒硝、硫安、乳糖、等）を用いた場合に
は、上記の均一混合物、または常法の乾式造粒法
により造粒して顆粒状の組成物とした。
得られた組成物は、当初、溶液状でも、顆粒状
のものでも、水で希釈すると、均一な水溶液とな
り噴霧施用に適した。[Table] As is clear from the results in Table 1, the anionic surfactant used significantly promoted the absorption and transfer of SF-1293 substance or its salt into plants compared to the control test. Even when compared with the comparative example, it is clear that it is significantly superior. Note that when only the anionic surfactant was applied, no phytotoxic effects on the test plants were observed. Examples 1 to 86 Each component shown in Table 2 below was
A mixture was prepared by uniformly mixing the ingredients in amounts that would give the proportions (wt%) shown in the table. When water was used as a carrier, the mixture resulted in a composition in the form of a syflop-like solution. On the other hand, when a substance other than water (such as Glauber's salt, ammonium sulfate, lactose, etc.) is used as a carrier, a granular composition is obtained by using the above-mentioned homogeneous mixture or by granulating it by a conventional dry granulation method. The resulting composition, whether initially in the form of a solution or granules, becomes a homogeneous aqueous solution when diluted with water and is suitable for spray application.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
試験例２ 殺草活性の評価
禾本科雑草のメヒシバ（Digitaria ciliaris
（RETZ）KOELER）と広葉雑草にイヌタデ
（Polygonum longisetum DE BRUYN.）に対
する殺草活性を評価した。各々の雑草は温室内で
生育させ、メヒシバは５葉期草丈20cmの時に、イ
ヌタデは６〜７葉期、草丈15cmの時に用いた。散
布薬液は前記の実施例１〜86に示した処方製剤の
ヘクタール当り3.0，4.0および5.0Kg相当量をヘク
タール当り１Kl相当量の水で希釈して雑草の茎葉
全体に散布処理した。
結果は薬剤散布後14日目に残草生重を測定し、
無処理区に対する殺草率（％）で表わした。なお
試験はｎ＝５で行ない、試験結果は、平均値とし
て第３表に示した。[Table] Test Example 2 Evaluation of herbicidal activity Digitaria ciliaris
(RETZ) KOELER) and the broad-leaved weed Polygonum longisetum DE BRUYN. Each weed was grown in a greenhouse, and the crabgrass was used at the 5-leaf stage and a plant height of 20 cm, and the Japanese knotweed was used at the 6-7 leaf stage and a plant height of 15 cm. The sprayed chemicals were prepared by diluting 3.0, 4.0, and 5.0 kg per hectare of the prescribed preparations shown in Examples 1 to 86 with water equivalent to 1 Kl per hectare and spraying them over the entire foliage of weeds. The results were determined by measuring the fresh weight of remaining grass on the 14th day after spraying the chemical.
It was expressed as a weed killing rate (%) compared to the untreated area. The test was conducted with n=5, and the test results are shown in Table 3 as average values.
【表】【table】
【表】【table】
【表】
(注) 参考例に用いた比較処方は次の
通りである。
参考例 １
SF−1293物質ナトリウム塩： 20％
芒硝： 80％
参考例 ２
SF−1293物質ナトリウム塩： 30％
ドデシルトリメチルアンモニウムクロライド：
５％
ポリオキシエチレン（＝15）オレイルアミ
ン： ５％
ポリオキシエチレン（＝13）ノニルフエニル
エーテル： ５％
水： 55％
参考例 ３
SF−1293物質ナトリウム塩： 30％
ドデシルトリメチルアンモニウムクロライド：
５％
ポリオキシエチレン（＝15）オレイルアミ
ン： ５％
ポリオキシエチレン（＝15）グリセリン骨油
脂肪酸エステル： ５％
水： 55％
第２表において、実施例中、SF−1293物質ナ
トリウム塩を20％含有する処方は、いずれも参考
例２および３（それぞれSF−1293物質ナトリウム
塩を30％含有）と同等またはそれ以上の活性であ
り、有効成分当りの薬効が著しく増強された。な
お、参考例２および３は特開昭60−4112号に示さ
れている処方である。
試験例３ 耐雨性試験
メヒシバに前記の実施例の組成物を水で希釈し
た散布薬液を散布し、散布後、２時間または６時
間後に人工降雨（20mm／時間）を１時間降らせ
た。薬剤散布後14日目に残草生重を測定し、無処
理区に対する殺草率（％）で本発明組成物の耐雨
性を試験した。本発明組成物は製剤量でヘクター
ル当り4.0Kgをヘクタール当り１Kl相当量の水で
希釈して茎葉全面に散布処理した。メヒシバの処
理時の草丈は20cm（約５葉）であつた。殺草率は
10連制の平均値で示した。試験結果を第４表に示
す。[Table] (Note) The comparative formulations used in the reference examples are as follows.
Reference example 1 SF-1293 substance sodium salt: 20% Glauber's salt: 80% Reference example 2 SF-1293 substance sodium salt: 30% Dodecyltrimethylammonium chloride:
5% Polyoxyethylene (=15) oleylamine: 5% Polyoxyethylene (=13) nonyl phenyl ether: 5% Water: 55% Reference example 3 SF-1293 substance sodium salt: 30% Dodecyltrimethylammonium chloride:
5% Polyoxyethylene (=15) oleylamine: 5% Polyoxyethylene (=15) glycerin bone oil fatty acid ester: 5% Water: 55% In Table 2, in the Examples, SF-1293 substance sodium salt was 20% Both of the formulations contained had the same or higher activity as Reference Examples 2 and 3 (each containing 30% SF-1293 substance sodium salt), and the medicinal efficacy per active ingredient was significantly enhanced. Note that Reference Examples 2 and 3 are the formulations shown in JP-A-60-4112. Test Example 3 Rain Resistance Test A spray solution prepared by diluting the composition of the above example with water was sprayed on crabgrass, and 2 hours or 6 hours after the spraying, artificial rain (20 mm/hour) was applied for 1 hour. The fresh weight of remaining grass was measured 14 days after the chemical spraying, and the rain resistance of the composition of the present invention was tested based on the herbicidal rate (%) relative to the untreated area. The composition of the present invention was applied at a dosage of 4.0 Kg per hectare, diluted with water equivalent to 1 Kl per hectare, and sprayed over the entire surface of the foliage. The plant height at the time of treatment was 20 cm (approximately 5 leaves). The weed killing rate is
It is shown as the average value of 10 consecutive series. The test results are shown in Table 4.
【表】【table】
【表】
と同じである
本発明の実施例による組成物を用いた場合はい
ずれも参考例１，２及び３と比較して優れた耐雨
性のあることが認められた。[Table] The compositions according to the examples of the present invention were all found to have excellent rain resistance compared to Reference Examples 1, 2, and 3.
Claims (1)
ト系、スルホネート系、ホスフエート系又はカル
ボン酸系陰イオン性界面活性剤の１種又は２種以
上とを、(a)：(b)の割合（重量比）が１：0.5〜
１：20の範囲で含有することを特徴とする殺草剤
組成物。 ２ (a)SF−1293物質又その塩と、(b)サルフエー
ト系、スルホネート系、ホスフエート系又はカル
ボン酸系陰イオン性界面活性剤の１種又は２種以
上と、(c)ポリオキシアルキレン系非イオン性界面
活性剤の１種又は２種以上とを、(a)：(b)の割合
（重量比）が１：0.5〜１：20の範囲で且つ(a)：(c)
の割合（重量比）が１：0.1〜１：20の範囲で含
有することを特徴とする殺草剤組成物。[Scope of Claims] 1. (a) SF-1293 substance or its salt; (b) one or more sulfate-based, sulfonate-based, phosphate-based, or carboxylic acid-based anionic surfactants; The ratio (weight ratio) of (a):(b) is 1:0.5~
A herbicide composition characterized by containing a herbicide in a range of 1:20. 2 (a) SF-1293 substance or its salt, (b) one or more sulfate-based, sulfonate-based, phosphate-based, or carboxylic acid-based anionic surfactants, and (c) polyoxyalkylene-based one or more nonionic surfactants in a ratio (weight ratio) of (a):(b) in the range of 1:0.5 to 1:20, and (a):(c)
A herbicide composition characterized in that the ratio (weight ratio) of the herbicide composition is in the range of 1:0.1 to 1:20.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13076085A JPS61289004A (en) | 1985-06-18 | 1985-06-18 | Weeding agent composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13076085A JPS61289004A (en) | 1985-06-18 | 1985-06-18 | Weeding agent composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61289004A JPS61289004A (en) | 1986-12-19 |
| JPH0433762B2 true JPH0433762B2 (en) | 1992-06-04 |
Family
ID=15041995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13076085A Granted JPS61289004A (en) | 1985-06-18 | 1985-06-18 | Weeding agent composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61289004A (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3809159A1 (en) * | 1988-03-18 | 1989-09-28 | Hoechst Ag | LIQUID HERBICIDES |
| DE59008283D1 (en) * | 1989-07-08 | 1995-03-02 | Hoechst Schering Agrevo Gmbh | Defoamer for liquid wetting agents and low-foaming liquid pesticides. |
| DE4029304A1 (en) * | 1990-09-15 | 1992-03-19 | Hoechst Ag | Synergistic herbicide mixts. - contain alkyl-polyglycol-ether! sulphate surfactant and a leaf-effective herbicide |
| US6930075B1 (en) | 1990-11-02 | 2005-08-16 | Monsanto Technology, Llc | Fatty acid-based herbicidal composition |
| ATE163125T1 (en) * | 1990-11-02 | 1998-02-15 | Safer Inc | FATTY ACID-BASED HERBICIDE COMPOSITION |
| US5196044A (en) * | 1991-01-08 | 1993-03-23 | Mycogen Corporation | Process and composition for controlling weeds |
| EP0577914A1 (en) * | 1992-07-08 | 1994-01-12 | Monsanto Europe S.A./N.V. | Improved glyphosate compositions and their use |
| US6774087B1 (en) | 1999-06-22 | 2004-08-10 | Fmc Corporation | Liquid herbicide composition |
| JP2001002516A (en) * | 1999-06-22 | 2001-01-09 | Nissan Chem Ind Ltd | Liquid herbicide composition |
| JP2005187418A (en) * | 2003-12-26 | 2005-07-14 | Nippon Nyukazai Kk | Agrochemical surfactant and agrochemical composition using the same |
| MX2007003193A (en) | 2004-09-17 | 2007-05-16 | Monsanto Technology Llc | Glyphosate formulations with early burndown symptoms. |
| EP1869978A1 (en) * | 2006-06-21 | 2007-12-26 | Bayer CropScience AG | Low-foaming preparations for crop protection |
| CN102027900B (en) * | 2009-09-28 | 2013-09-18 | 南京华洲药业有限公司 | Synergist and synergist-containing diquat aqueous solution |
| TWI561170B (en) * | 2010-12-21 | 2016-12-11 | Meiji Seika Pharma Co Ltd | Stabilized liquid aqueous crop protection composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS604112A (en) * | 1983-06-23 | 1985-01-10 | Meiji Seika Kaisha Ltd | Herbicide composition |
-
1985
- 1985-06-18 JP JP13076085A patent/JPS61289004A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS604112A (en) * | 1983-06-23 | 1985-01-10 | Meiji Seika Kaisha Ltd | Herbicide composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61289004A (en) | 1986-12-19 |
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| LAPS | Cancellation because of no payment of annual fees |