JPH04257503A - Herbicide composition - Google Patents
Herbicide compositionInfo
- Publication number
- JPH04257503A JPH04257503A JP3017513A JP1751391A JPH04257503A JP H04257503 A JPH04257503 A JP H04257503A JP 3017513 A JP3017513 A JP 3017513A JP 1751391 A JP1751391 A JP 1751391A JP H04257503 A JPH04257503 A JP H04257503A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- compound
- parts
- formula
- herbicidal
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title abstract description 38
- 230000002363 herbicidal effect Effects 0.000 title abstract description 26
- 239000004009 herbicide Substances 0.000 title abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 abstract description 14
- 241000196324 Embryophyta Species 0.000 abstract description 14
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 abstract description 12
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 6
- 235000005822 corn Nutrition 0.000 abstract description 6
- 239000002689 soil Substances 0.000 abstract description 6
- 230000035784 germination Effects 0.000 abstract description 4
- 231100000674 Phytotoxicity Toxicity 0.000 abstract description 2
- 241000209149 Zea Species 0.000 abstract 2
- 238000009472 formulation Methods 0.000 description 10
- -1 sodium alkylaryl sulfonate Chemical class 0.000 description 10
- 239000008187 granular material Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 239000004563 wettable powder Substances 0.000 description 7
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 239000003549 soybean oil Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 239000000440 bentonite Substances 0.000 description 4
- 229910000278 bentonite Inorganic materials 0.000 description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000005469 granulation Methods 0.000 description 3
- 230000003179 granulation Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000002552 dosage form 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
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical class FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
- 241000270722 Crocodylidae Species 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 239000005504 Dicamba Substances 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 241000380130 Ehrharta erecta Species 0.000 description 1
- 239000005561 Glufosinate Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000005573 Linuron Substances 0.000 description 1
- 239000005583 Metribuzin Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000005586 Nicosulfuron Substances 0.000 description 1
- 239000005591 Pendimethalin Substances 0.000 description 1
- 229920001213 Polysorbate 20 Chemical class 0.000 description 1
- GPGLBXMQFQQXDV-UHFFFAOYSA-N Primisulfuron Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 GPGLBXMQFQQXDV-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- IBZHOAONZVJLOB-UHFFFAOYSA-N Tridiphane Chemical compound ClC1=CC(Cl)=CC(C2(CC(Cl)(Cl)Cl)OC2)=C1 IBZHOAONZVJLOB-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 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 description 1
- 239000000575 pesticide Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Chemical class 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Chemical class 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【0001】0001
【産業上の利用分野】本発明は、2種類の公知の除草活
性成分を混合することにより各種の有害な雑草を効率的
に防除する除草剤組成物に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a herbicidal composition that efficiently controls various harmful weeds by mixing two known herbicidal active ingredients.
【0002】0002
【従来の技術及び課題】長年にわたる除草剤の研究開発
の中から多種多様な薬剤が実用化され、これら除草剤は
雑草防除作業の省力化や農園芸作物の生産性向上に寄与
してきた。今日においても、より優れた除草特性を有す
る新規薬剤の開発が要望され、特に農園芸用除草剤とし
ては、栽培作物に薬害を及ぼすことなく、対象雑草のみ
を選択的にかつ低薬量で防除しうることが望ましいが、
既存の薬剤は必ずしもこの要求を満たすものではない。BACKGROUND OF THE INVENTION A wide variety of herbicides have been put into practical use through many years of research and development on herbicides, and these herbicides have contributed to saving labor in weed control work and improving the productivity of agricultural and horticultural crops. Even today, there is a demand for the development of new chemicals with better herbicidal properties, and in particular, as herbicides for agriculture and horticulture, they are used to selectively control only target weeds at low doses without causing harm to cultivated crops. It is desirable to be able to do so, but
Existing drugs do not necessarily meet this requirement.
【0003】式(1)で表される化合物(以下、化合物
(1)と称する)は、特開平2−173号公報記載の公
知の化合物で、従来の除草剤に比して低薬量で優れた除
草効果をあげ、なおかつトウモロコシ、コムギ等の作物
に対して高い安全性を有するが、一部の雑草で効果が劣
るものがある。一方、式(2)で表される化合物(一般
名アラクロール)、式(3)で表される化合物(一般名
メトラクロール)及び式(4)で表される化合物(一般
名アセトクロール)は、実用場面で使用されており、イ
ネ科雑草に高い効果を有するが、広葉雑草には効果が劣
る場合が多く、その使用薬量も高い。[0003] The compound represented by formula (1) (hereinafter referred to as compound (1)) is a known compound described in JP-A-2-173, and is used in lower doses than conventional herbicides. Although it has excellent herbicidal effects and is highly safe for crops such as corn and wheat, it is less effective against some weeds. On the other hand, the compound represented by formula (2) (generic name alachlor), the compound represented by formula (3) (generic name metolachlor), and the compound represented by formula (4) (generic name acetochlor) are It is used in practical situations and is highly effective against grass weeds, but it is often less effective against broad-leaved weeds, and the dosage is also high.
【0004】0004
【化2】[Case 2]
【0005】[0005]
【問題を解決するための手段】本発明は、化合物(1)
と、アラクロール、メトラクロール及びアセトクロール
から選ばれる1種を有効成分として含有する除草剤組成
物(以下、本発明組成物と称する)に関する。本発明組
成物は、本発明組成物中に含まれる化合物(1)と、ア
ラクロール、メトラクロールまたはアセトクロールのそ
れぞれの除草効果が単に相加的に得られるだけではなく
、相乗的な作用を有し、それぞれの使用薬量を低減でき
る。[Means for solving the problem] The present invention provides compound (1)
and a herbicide composition (hereinafter referred to as the composition of the present invention) containing one selected from alachlor, metolachlor, and acetochlor as an active ingredient. The composition of the present invention has the herbicidal effects of compound (1) and alachlor, metolachlor, or acetochlor contained in the composition of the present invention not only additively but also synergistically. The amount of each drug used can be reduced.
【0006】また、本発明組成物は、トウモロコシに対
して薬害を及ぼすことなく、低薬量で一年生及び多年生
のイネ科雑草、広葉雑草及びカヤツリグサ科雑草を完全
に防除でき、実用場面での有用性は極めて高い。本発明
組成物は、雑草の発芽後茎葉処理にても効果を奏するが
、発芽前土壌処理がより効果的である。また、トウモロ
コシ以外の各種穀類に対しても有用であり、その他の畑
地、果樹園などの農園芸分野及び運動場、空き地、林地
、タンクヤード、線路端などの非農耕地における各種雑
草の防除にも適用でき、雑草防除にあたって大きな経済
的効果を示す。[0006] Furthermore, the composition of the present invention can completely control annual and perennial grass weeds, broad-leaved weeds, and Cyperaceae weeds at low doses without causing any phytotoxicity to corn, and is therefore useful in practical situations. The quality is extremely high. Although the composition of the present invention is effective in treating the foliage of weeds after germination, pre-emergence soil treatment is more effective. It is also useful for various grains other than corn, and can also be used to control various weeds in agricultural and horticultural fields such as fields and orchards, as well as non-agricultural lands such as playgrounds, vacant lots, forest lands, tank yards, and railway edges. It can be applied and shows great economic effect in weed control.
【0007】本発明組成物は、アラクロール、メトラク
ロールあるいはアセトクロール1重量部当たり化合物(
1)を0.001 〜10重量部含む。好ましくは、ア
ラクロール、メトラクロールあるいはアセトクロール1
重量部当たり化合物(1)を0.01〜1重量部含む。
本発明組成物の処理薬量は、生育を阻止すべき特定の対
象植物の種類などにより左右されるが、有効成分として
化合物(1)が1g〜1kg/ha、好ましくは 10
g〜0.5kg/haであり、アラクロール、メトラク
ロールあるいはアセトクロールが 10g〜5kg/h
a、好ましくは 50g〜3kg/haである。The composition of the present invention contains a compound (
Contains 0.001 to 10 parts by weight of 1). Preferably alachlor, metolachlor or acetochlor 1
It contains 0.01 to 1 part by weight of compound (1) per part by weight. The treatment amount of the composition of the present invention depends on the type of specific target plant whose growth is to be inhibited, but the amount of compound (1) as an active ingredient is 1 g to 1 kg/ha, preferably 10
g ~ 0.5 kg/ha, and alachlor, metolachlor or acetochlor 10 g ~ 5 kg/h
a, preferably 50g to 3kg/ha.
【0008】本発明組成物は、通常固体または液体希釈
液からなる担体と混合した製剤の形態で使用するが、界
面活性剤を更に混合した製剤の形態での使用が好ましい
。担体として、例えば、クレー、タルク、ベントナイト
、珪藻土、ホワイトカーボン等の固体担体及び水、アル
コール類(イソプロパノール、ブタノール、ベンジルア
ルコール、フルフリルアルコール等)、芳香族炭化水素
類(トルエン、キシレン等)、塩素化炭化水素類(クロ
ロベンゼン等)、エーテル類(アニソール等)、ケトン
類(シクロヘキサノン、イソホロン等)、エステル類(
酢酸ブチル等)、酸アミド類(N−メチルピロリドン等
)等の液体担体があげられる。The composition of the present invention is usually used in the form of a preparation mixed with a carrier consisting of a solid or liquid diluent, but it is preferably used in the form of a preparation further mixed with a surfactant. Examples of carriers include solid carriers such as clay, talc, bentonite, diatomaceous earth, and white carbon, water, alcohols (isopropanol, butanol, benzyl alcohol, furfuryl alcohol, etc.), aromatic hydrocarbons (toluene, xylene, etc.), Chlorinated hydrocarbons (chlorobenzene, etc.), ethers (anisole, etc.), ketones (cyclohexanone, isophorone, etc.), esters (
butyl acetate, etc.), acid amides (N-methylpyrrolidone, etc.), and the like.
【0009】界面活性剤として、例えば、アルキルアリ
ールスルホン酸ナトリウム、アルキルナフタレンスルホ
ン酸ナトリウム、ジアルキル琥珀酸ナトリウム、ポリオ
キシエチレンアルキルアリールエーテルサルフェート、
アルキル型燐酸エステル、アルキルフェノール型燐酸エ
ステル等のアニオン系界面活性剤、ポリオキシエチレン
アルキルエーテル、ポリオキシエチレンアルキルアリー
ルエーテル、ポリオキシエチレン(プロピレン)脂肪酸
エステル、ソルビタンモノオレート、ポリオキシエチレ
ンソルビタンモノラウレート等のノニオン系界面活性剤
、ポリオキシエチレン硬化ヒマシ油のような植物油誘導
体があげられる。Examples of surfactants include sodium alkylaryl sulfonate, sodium alkylnaphthalene sulfonate, sodium dialkyl succinate, polyoxyethylene alkylaryl ether sulfate,
Anionic surfactants such as alkyl phosphate esters and alkylphenol phosphate esters, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene (propylene) fatty acid esters, sorbitan monooleate, polyoxyethylene sorbitan monolaurate and vegetable oil derivatives such as polyoxyethylene hydrogenated castor oil.
【0010】本発明組成物は、所望により乳化剤、湿潤
剤、分散剤、結合剤、浸透剤、展着剤、安定剤などを添
加し、乳剤剤、液剤、水和剤、粉剤、粒剤、顆粒剤、懸
濁剤等任意の剤型にて実用に供することができる。この
際、同時に複数の公知除草剤との混合使用も可能である
。本発明組成物と混用使用するのに好ましい薬剤として
、1989年版農薬データブック(ソフトサイエンス社
発行)に記載されたアトラジン(atrazine)、
シマジン(simazine)、シアナジン(cyan
azine) 、グリホサート(glyphosate
)、ビアラホス(bialaphos) 、パラコート
(paraquat)、ディカンバ(dicamba)
、クロラミベン(chloramben)、ベンタゾ
ン(bentazone) 、イーピーティーシー(E
PTC)、グルホシネート(glufosinate)
、ブチレート(butylate)、ディウロン(d
iuron)、リニュロン(linuron) 、メト
リブジン(metribuzin)、ペンディメタリン
(pendimethalin) 、2,4−ディー(
2,4−D) 、エムシーピー(MCP) 及びトリデ
ィファン(tridiphane)、その他にニコスル
フロン(nicosulfuron)、プリミスルフロ
ン(primisulfuron) 等があげられる。The composition of the present invention can be prepared by adding emulsifiers, wetting agents, dispersants, binders, penetrants, spreading agents, stabilizers, etc. as desired, to form emulsions, solutions, wettable powders, powders, granules, etc. It can be put to practical use in any dosage form such as granules and suspensions. At this time, it is also possible to use the compound simultaneously with a plurality of known herbicides. Preferred drugs to be used in combination with the composition of the present invention include atrazine, which is listed in the 1989 Pesticide Data Book (published by Soft Science);
simazine, cyanazine
azine), glyphosate
), bialaphos, paraquat, dicamba
, chloramben, bentazone, E.P.C.
PTC), glufosinate
, butylate, diuron (d
iuron), linuron, metribuzin, pendimethalin, 2,4-di(
2,4-D), MCP, and tridiphane, as well as nicosulfuron, primisulfuron, and the like.
【0011】除草剤混合物の相乗的除草効果については
、次のように説明することができる。即ち、個々の活性
化合物は、その除草活性にそれぞれ欠点を示す場合が多
くあるが、その場合2種の活性化合物を組合せた除草活
性が、その2種の化合物の各々の活性の単純な合計(期
待される活性)よりも大きくなる場合にこれを相乗作用
という。2種の除草剤の特定組合せにより期待される活
性は、次のように計算することができる。(コルビー(
Colby S.R. )、除草剤の組合せの相乗お
よび拮抗作用反応の計算、ウィード(Weed)、第1
5巻、20〜22頁(1967年)を参照)
E=α+β−(α・β/100)
α:除草剤Aをakg/ha の量で処理した時の抑制
率β:除草剤Bをbkg/ha の量で処理した時の抑
制率E:除草剤Aをakg/ha 、除草剤Bをbkg
/ha の量で処理した場合に期待される抑制率
即ち、実際の抑制率が上記計算より大きいならば組合せ
による活性は相乗作用を示すということができる。The synergistic herbicidal effect of herbicide mixtures can be explained as follows. That is, individual active compounds often exhibit drawbacks in their herbicidal activity, but in such cases, the herbicidal activity of the combination of two active compounds is simply the sum of the activities of each of the two compounds ( When the activity is greater than the expected activity, this is called synergism. The expected activity of a particular combination of two herbicides can be calculated as follows. (Colby (
Colby S. R. ), Calculation of synergistic and antagonistic responses of herbicide combinations, Weed, Vol.
5, pp. 20-22 (1967)) E=α+β−(α・β/100) α: Inhibition rate when herbicide A is treated at a kg/ha amount β: Herbicide B at bkg Suppression rate E when treated at an amount of /ha: akg/ha of herbicide A, bkg of herbicide B
If the expected inhibition rate, that is, the actual inhibition rate when treated at an amount of /ha is greater than the above calculation, it can be said that the combined activity exhibits a synergistic effect.
【0012】0012
【実施例】以下本発明組成物を実施例によりさらに具体
的に説明するが、本発明における化合物、製造量、剤型
等は実施例のみに限定されるものではない。なお、「部
」は全て重量部を意味する。
〔配合実施例1〕 水和剤
化合物(1) ─────── 2
部アラクロール ───────
24 部ジークライトPFP ──────
─ 66 部(カオリンクレー:ジークライト
工業(株)商品名)ソルポール5039 ───
──── 2 部(湿潤分散剤:東邦化学
(株)商品名)大豆油 ───
──── 2 部カープレックス
0 ─────── 4 部(ホワイトカ
ーボン:シオノギ製薬(株)商品名)以上を均一に混合
粉砕して水和剤とする。[Examples] The composition of the present invention will be explained in more detail below with reference to Examples, but the compounds, production amounts, dosage forms, etc. of the present invention are not limited to the Examples. In addition, all "parts" mean parts by weight. [Formulation Example 1] Wettable powder compound (1) ─────── 2
Part Alacrol ────────
24 Part Sieglite PFP ──────
─ Part 66 (Kaolin clay: Sieglite Industries Co., Ltd. product name) Solpol 5039 ──
──── 2 parts (wetting and dispersing agent: Toho Chemical Co., Ltd. trade name) soybean oil ────
──── 2 parts Carplex 0 ──────── 4 parts or more (white carbon: Shionogi Pharmaceutical Co., Ltd. trade name) are mixed and ground uniformly to make a wettable powder.
【0013】〔配合実施例2〕 水和剤化合物(1)
─────── 2 部メト
ラクロール ─────── 20 部
ジークライトPFP ─────── 70
部ソルポール5039 ───────
2 部大豆油 ──
───── 2 部カープレックス
0 ─────── 4 部以上を均一に
混合粉砕して水和剤とする。[Formulation Example 2] Wettable powder compound (1)
─────── 2 parts Metolachlor ─────── 20 parts Siegrite PFP ──────── 70
Part Solpol 5039 ────────
Part 2 Soybean oil ──
────── 2 parts Carplex 0 ─────── 4 parts or more are mixed and ground uniformly to make a wettable powder.
【0014】〔配合実施例3〕 水和剤化合物(1)
─────── 3 部メト
ラクロール ─────── 27 部
ジークライトPFP ─────── 62
部ソルポール5039 ───────
2 部大豆油 ──
───── 2 部カープレックス
0 ─────── 4 部以上を均一に
混合粉砕して水和剤とする。[Formulation Example 3] Wettable powder compound (1)
─────── 3 parts Metolachlor ─────── 27 parts Siegrite PFP ─────── 62
Part Solpol 5039 ────────
Part 2 Soybean oil ──
────── 2 parts Carplex 0 ─────── 4 parts or more are mixed and ground uniformly to make a wettable powder.
【0015】〔配合実施例4〕 乳剤化合物(1)
─────── 3 部アラク
ロール ─────── 35 部
キシレン ─────── 47
部メチルナフタレン ─────── 1
0 部ソルポール 2680 ──────
─ 5 部(非イオン性界面活性剤とアニ
オン界面活性剤との混合物:東邦化学工業(株)商品名
)
以上を均一に混合溶解して乳剤とする。[Formulation Example 4] Emulsion compound (1)
─────── 3 parts alachlor ─────── 35 parts xylene ─────── 47
Part methylnaphthalene ──────── 1
0 part Solpol 2680 ──────
- 5 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) The above are uniformly mixed and dissolved to form an emulsion.
【0016】〔配合実施例5〕 乳剤化合物(1)
─────── 2 部メトラ
クロール ─────── 25 部キ
シレン ─────── 58
部メチルナフタレン ─────── 10
部ソルポール 2680 ───────
5 部以上を均一に混合溶解して乳剤と
する。[Formulation Example 5] Emulsion compound (1)
──────── 2 parts metolachlor ─────── 25 parts xylene ──────── 58
Part methylnaphthalene ──────── 10
Department Solpol 2680 ────────
5 parts or more are uniformly mixed and dissolved to form an emulsion.
【0017】〔配合実施例6〕 乳剤化合物(1)
─────── 4 部アセト
クロール ─────── 32 部キ
シレン ─────── 49
部メチルナフタレン ─────── 10
部ソルポール 2680 ───────
5 部以上を均一に混合溶解して乳剤と
する。[Formulation Example 6] Emulsion compound (1)
─────── 4 parts acetochlor ─────── 32 parts xylene ──────── 49
Part methylnaphthalene ──────── 10
Department Solpol 2680 ────────
5 parts or more are uniformly mixed and dissolved to form an emulsion.
【0018】〔配合実施例7〕 粒剤化合物(1)
───────0.7 部アラクロー
ル ─────── 10 部DB
SN ─────── 3
部(ドデシルベンゼンスルホン酸ナトリウム)エ
ポキシ化大豆油 ─────── 1
部ベントナイト ─────── 30
部タルク ──────
─ 55.3部以上を均一に混合粉砕して、少量の水
を加え攪拌し、押出造粒機で造粒し、造粒後乾燥して粒
剤を得た。[Formulation Example 7] Granule Compound (1)
───────0.7 Part Alacrol ─────── 10 Part DB
SN ──────── 3
Part (sodium dodecylbenzenesulfonate) Epoxidized soybean oil ─────── 1
Part bentonite ──────── 30
Part Tarc ──────
- 55.3 parts or more were uniformly mixed and pulverized, a small amount of water was added and stirred, granulated using an extrusion granulator, and after granulation, the mixture was dried to obtain granules.
【0019】〔配合実施例8〕 粒剤化合物(1)
─────── 1 部メトラ
クロール ─────── 10 部D
BSN ─────── 3
部エポキシ化大豆油 ───────
1 部ベントナイト ──────
─ 30 部タルク
─────── 55 部以上を均一に混合粉
砕して、少量の水を加え攪拌し、押出造粒機で造粒し、
造粒後乾燥して粒剤を得た。[Formulation Example 8] Granule Compound (1)
──────── 1 part metolachlor ─────── 10 part D
BSN ──────── 3
Epoxidized soybean oil ────────
Part 1 Bentonite ──────
─ 30 parts talc
─────── 55 parts or more are uniformly mixed and pulverized, a small amount of water is added and stirred, and granulated using an extrusion granulator.
After granulation, the mixture was dried to obtain granules.
【0020】〔配合実施例9〕 粒剤化合物(1)
─────── 1 部アセト
クロール ─────── 8 部
DBSN ───────
3 部エポキシ化大豆油 ───────
1 部ベントナイト ─────
── 30 部タルク
─────── 57 部以上を均一に混合
粉砕して、少量の水を加え攪拌し、押出造粒機で造粒し
、造粒後乾燥して粒剤を得た。[Formulation Example 9] Granule Compound (1)
─────── 1 part acetochlor ─────── 8 parts DBSN ───────
3 parts epoxidized soybean oil ────────
Part 1 Bentonite ──────
── 30 parts talc
──────── 57 parts or more were uniformly mixed and pulverized, a small amount of water was added and stirred, and the mixture was granulated using an extrusion granulator, and after granulation, it was dried to obtain granules.
【0021】〔試験例〕 発芽前土壌処理による除草
効果試験
縦30cm、横30cm、深さ10cmのプチスチック
製箱に殺菌した畑地土壌を入れ、トウモロコシ、エノコ
ログサ、イチビ、アオビユ、シロザの種子を各々スポッ
ト状に植え、覆土した。播種翌日に5 l/aの散布水
量で土壌を処理を行った。散布の際の薬液は、前記配合
例1、2及び3に準じて適宜調整された水和剤を水で希
釈して小型スプレーで散布した。薬液散布3週間後、各
雑草の地上部生体重を測定し、次の式で抑制率(%)を
求めた。[Test Example] Weeding effect test by pre-germination soil treatment Sterilized upland soil is placed in a plastic box measuring 30 cm long, 30 cm wide and 10 cm deep, and seeds of corn, foxtail grass, Japanese crocodile, Japanese cabbage, and white cabbage are placed in spots respectively. They were planted in shapes and covered with soil. The day after sowing, the soil was treated with a water spray of 5 l/a. The chemical solution used for spraying was a wettable powder suitably prepared according to Formulation Examples 1, 2, and 3, diluted with water, and sprayed using a small sprayer. Three weeks after spraying the chemical solution, the above-ground fresh weight of each weed was measured, and the suppression rate (%) was calculated using the following formula.
【0022】[0022]
【数1】
抑制率(%)=(1−処理区の地上部生体重/無処理区
の地上部生体重)×100 第1表に化合物(1)、ア
ラクロール,メトラクロール及びアセトクロールの単剤
の除草効果試験結果を示した。第2表に化合物(1)と
、アラクロール、メトラクロール及びアセトクロールと
の組成物の除草効果試験結果を示した。[Equation 1] Suppression rate (%) = (1 - above-ground fresh weight of treated area / above-ground fresh weight of non-treated area) x 100 Table 1 shows the inhibition rate of compound (1), alachlor, metolachlor and acetochlor. The herbicidal effect test results of single agents are shown. Table 2 shows the herbicidal effect test results of the compositions of compound (1), alachlor, metolachlor, and acetochlor.
【0023】なお、表中の記号は以下を表す。
A:トウモロコシ、B:エノコログサ、C:イチビ、D
:アオビユ、E:シロザ[0023] The symbols in the table represent the following. A: Corn, B: Wild foxtail, C: Ichibi, D
: Aobyu, E: Shiroza
【0024】[0024]
【表1】[Table 1]
【0025】[0025]
【表2】
第2表 混合剤の除草効果の実測値と期待値
(抑制率,%) ────────────────
───────────────── 各有効成分
A B
C D E の処
理薬量 実 期 実 期
実 期 実 期 実 期
(g/ha) 測 待
測 待 測 待 測 待 測
待 値
値 値 値 値 値 値
値 値 値────────────────
────────────────── アラクロー
ル+化合物(1)
120 + 10 0 0
100 81 86 57 10
0 75 100 89 120 + 3
0 0 0 100 95
100 91 100 96 10
0 98 360 + 10
0 0 100 94 96 64
100 92 100 97 360
+ 30 0 0 10
0 98 100 92 100 99
100 99───────────────
─────────────────── メトラク
ロール+化合物(1)
120 + 10 0 0
100 88 83 55 10
0 69 100 85 120 + 3
0 0 0 100 97
100 90 100 95 10
0 97 360 + 10
0 0 100 95 93 62
100 83 100 96 360
+ 30 0 0 10
0 99 100 92 100 97
100 99───────────────
──────────────────── アセト
クロール+化合物(1)
80 + 10 0 0
100 84 91 60 10
0 82 100 89 80 + 3
0 0 0 100 96
100 91 100 97 10
0 98 240 + 10
0 0 100 95 100 81
100 95 100 98 240
+ 30 0 0 10
0 99 100 96 100 99
100 100───────────────
──────────────────── (表中
、期待値は前記コルビーの式より求めた値を示す。)以
上の結果から明らかなように、本発明組成物の除草効果
は、化合物(1)と、アラクロール、メトラクロールあ
るいはアセトクロールとを混合した場合のそれぞれの合
計にとどまらず、相乗効果的除草活性を有しており、更
に低薬量で対象雑草を選択的に防除することができる。[Table 2] Table 2 Actual and expected values of herbicidal effect of mixture (inhibition rate, %) ────────────────
────────────────── Each active ingredient
A B
Processing amount of CDE Actual period Actual period
Actual period Actual period Actual period
(g/ha)
Measurement standby value
value value value value value value value
Value Value Value────────────────
────────────────── Alachlor + Compound (1) 120 + 10 0 0
100 81 86 57 10
0 75 100 89 120 + 3
0 0 0 100 95
100 91 100 96 10
0 98 360 + 10
0 0 100 94 96 64
100 92 100 97 360
+ 30 0 0 10
0 98 100 92 100 99
100 99────────────────
──────────────────── Metolachlor + Compound (1) 120 + 10 0 0
100 88 83 55 10
0 69 100 85 120 + 3
0 0 0 100 97
100 90 100 95 10
0 97 360 + 10
0 0 100 95 93 62
100 83 100 96 360
+ 30 0 0 10
0 99 100 92 100 97
100 99────────────────
──────────────────── Acetochlor + Compound (1) 80 + 10 0 0
100 84 91 60 10
0 82 100 89 80 + 3
0 0 0 100 96
100 91 100 97 10
0 98 240 + 10
0 0 100 95 100 81
100 95 100 98 240
+ 30 0 0 10
0 99 100 96 100 99
100 100────────────────
──────────────────── (In the table, the expected value indicates the value obtained from the Colby equation.) As is clear from the above results, the present invention The herbicidal effect of the composition is not limited to the sum of compound (1) and alachlor, metolachlor, or acetochlor, but also has synergistic herbicidal activity, and furthermore, it has a synergistic herbicidal activity at a low dose. Target weeds can be selectively controlled.
Claims (1)
)で表される化合物、式(3)で表される化合物及び式
(4)で表される化合物から選ばれる1種を有効成分と
して含有する除草剤組成物。 【化1】[Claim 1] A compound represented by formula (1) and a compound represented by formula (2)
), a compound represented by formula (3), and a compound represented by formula (4), as an active ingredient. [Chemical formula 1]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3017513A JPH04257503A (en) | 1991-02-08 | 1991-02-08 | Herbicide composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3017513A JPH04257503A (en) | 1991-02-08 | 1991-02-08 | Herbicide composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04257503A true JPH04257503A (en) | 1992-09-11 |
Family
ID=11946052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3017513A Pending JPH04257503A (en) | 1991-02-08 | 1991-02-08 | Herbicide composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04257503A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995004054A1 (en) * | 1993-08-02 | 1995-02-09 | Idemitsu Kosan Co., Ltd. | Pyrazole derivative |
US5767289A (en) * | 1993-08-02 | 1998-06-16 | Idemitsu Kosan Company, Limited | Aromatic carboxylic acid bicyclic sulfur compounds |
KR100411186B1 (en) * | 2000-12-21 | 2003-12-18 | 한국생명공학연구원 | The biocontrol agent containing aminoglycoside antibiotics for control of plant diseases |
WO2008093840A1 (en) * | 2007-02-02 | 2008-08-07 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal compositions containing benzoylpyrazole compounds |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH0357587U (en) * | 1989-10-06 | 1991-06-03 | ||
JPH04224395A (en) * | 1990-12-25 | 1992-08-13 | Yoshinori Miyake | Pipe passage apparatus setting mechanism |
-
1991
- 1991-02-08 JP JP3017513A patent/JPH04257503A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0357587U (en) * | 1989-10-06 | 1991-06-03 | ||
JPH04224395A (en) * | 1990-12-25 | 1992-08-13 | Yoshinori Miyake | Pipe passage apparatus setting mechanism |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995004054A1 (en) * | 1993-08-02 | 1995-02-09 | Idemitsu Kosan Co., Ltd. | Pyrazole derivative |
US5767289A (en) * | 1993-08-02 | 1998-06-16 | Idemitsu Kosan Company, Limited | Aromatic carboxylic acid bicyclic sulfur compounds |
US6063936A (en) * | 1993-08-02 | 2000-05-16 | Idemitsu Kosan Co., Ltd. | Aromatic carboxylic acid bicyclic sulfur compounds |
US6103668A (en) * | 1993-08-02 | 2000-08-15 | Idemitsu Kosan Co., Ltd. | Pyrazole derivatives |
US6136755A (en) * | 1993-08-02 | 2000-10-24 | Idemitsu Kosan Co., Ltd. | Pyrazole derivatives |
US6677460B1 (en) | 1993-08-02 | 2004-01-13 | Idemitsu Kosan Company, Limited | Aromatic carboxylic acid bicyclic sulfur compounds |
KR100411186B1 (en) * | 2000-12-21 | 2003-12-18 | 한국생명공학연구원 | The biocontrol agent containing aminoglycoside antibiotics for control of plant diseases |
WO2008093840A1 (en) * | 2007-02-02 | 2008-08-07 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal compositions containing benzoylpyrazole compounds |
JP2009013161A (en) * | 2007-02-02 | 2009-01-22 | Ishihara Sangyo Kaisha Ltd | Herbicidal composition containing benzoylpyrazole compound |
US20100099563A1 (en) * | 2007-02-02 | 2010-04-22 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal compositions containing benzoylpyrazole compounds |
US8466088B2 (en) | 2007-02-02 | 2013-06-18 | Ishihara Sangyo Kaisha, Ltd. | Herbicidal compositions containing benzoylpyrazole compounds |
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