SI9400304A - Herbicide composition,activity-promoting agent for improving the efficacy of the herbicide, and a method for treating cultivated plants. - Google Patents
Herbicide composition,activity-promoting agent for improving the efficacy of the herbicide, and a method for treating cultivated plants. Download PDFInfo
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- SI9400304A SI9400304A SI9400304A SI9400304A SI9400304A SI 9400304 A SI9400304 A SI 9400304A SI 9400304 A SI9400304 A SI 9400304A SI 9400304 A SI9400304 A SI 9400304A SI 9400304 A SI9400304 A SI 9400304A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
Abstract
Description
Herbicidni sestavek, sredstvo, ki povišuje aktivnost za izboljšanje učinkovitosti herbicida in postopek za obdelovanje kultiviranih rastlinA herbicidal composition, an activity enhancer for improving herbicide efficiency and a process for cultivating cultivated plants
Predloženi izum se nanaša na herbicidni sestavek, ki vsebuje vsaj eno ali več aktivnih sestavin, znanih samih po sebi, kot npr. bipiridinski, hidroksibenzonitrilni, karbamoil fenil karbamatni, piridazinski, kinolinski, sulfonil sečninski ali triazinski herbicid, in enega ali več sredstev, ki povišujejo aktivnost za izboljšanje učinkovitosti aktivne sestavine/sestavin. Predloženi izum se nadalje nanaša na postopek za obdelovanje nasadov, kot npr. nasadov sladkorne pese, ipd. z uporabo herbicida, in na sredstvo, ki povišuje aktivnost za povečevanje učinkovitosti aktivne sestavine herbicida, kot npr. benzofuranske, bipiridinske, hidroksibenzonitrilne, karbamoil fenil karbamatne, piridazinske, kinolinske, sulfonil sečninske ali triazinske aktivne sestavine.The present invention relates to a herbicidal composition containing at least one or more active ingredients known per se, such as e.g. bipyridine, hydroxybenzonitrile, carbamoyl phenyl carbamate, pyridazine, quinoline, sulfonyl urea or triazine herbicide, and one or more activity enhancing agents for improving the active ingredient / ingredient performance. The present invention further relates to a process for cultivating plantations, such as e.g. beet plantations, etc. using a herbicide, and to an activity-enhancing agent for increasing the potency of the active ingredient of the herbicide, such as e.g. benzofuran, bipyridine, hydroxybenzonitrile, carbamoyl phenyl carbamate, pyridazine, quinoline, sulfonyl urea or triazine active ingredients.
Učinkovitost herbicidov, nanesenih na liste, lahko izboljšajo s površinsko aktivnimi aditivi, ki zmanjšujejo površinsko napetost herbicidov, s čimer tudi omogočijo, da se napršene kapljice razprostrejo na površinah listov in se na ta način poveča kontaktna površina med herbicidom in površino lista. Zaradi njihove lastnosti, da raztapljajo vosek, lahko lipofilne površinsko aktivne aditive uporabijo tudi zato, da zagotovijo bolj učinkovito penetracijo herbicidov. Hidrofilna površinsko aktivna sredstva lahko uporabijo za izboljšanje translokacije znotraj rastlin.The effectiveness of herbicides applied to the leaves can be improved with surfactant additives that reduce the surface tension of the herbicides, thereby allowing the spray droplets to spread on the leaf surfaces, thereby increasing the contact surface between the herbicide and the leaf surface. Due to their ability to dissolve wax, lipophilic surfactants can also be used to provide more effective penetration of herbicides. Hydrophilic surfactants can be used to enhance translocation within plants.
Običajno v vodi netopne aktivne sestavine formulirajo v emulzijske koncentrate in aktivne sestavine, netopne v organskih topilih, v omočljive praške. Vendar sta ti dve formulaciji uporabniku zelo neprijazni zaradi toksičnosti in vnetljivosti topil in problemov, ki nastanejo pri pakiranju materialov in shranjevanju. Omočljivi praški so problematični zaradi tvorbe težkega prahu.Usually water-insoluble active ingredients are formulated into emulsion concentrates and active ingredients insoluble in organic solvents into wettable powders. However, these two formulations are very unfriendly to the user due to the toxicity and flammability of the solvents and the problems that arise with the packaging of materials and storage. Wettable powders are problematic due to the formation of heavy dust.
Zaradi zgoraj opisanih problemov so na splošno poskušali priti do uporabniku bolj prijaznih suspenzij ali granul, suspendiranih v vodi. Vendar pa so v le-teh aktivne sestavine v obliki trdnih delcev, za razliko od emulzijskih koncentratov, kjer so v obliki raztopljenih molekul, s čimer se biološka učinkovitost na splošno izgubi, ker večji delci ne penetrirajo v rastline tako kot molekule.Because of the problems described above, they have generally attempted to obtain more user-friendly suspensions or granules suspended in water. However, in these, the active ingredients are in the form of solids, unlike emulsion concentrates, where they are in the form of dissolved molecules, which generally loses bioavailability because larger particles do not penetrate plants like molecules.
Zaradi zgoraj navedenega, je potrebno delce netopne aktivne sestavine zmleti v prašek z maksimalno finostjo in njihove penetracijske in translokacijske lastnosti izboljšati s sredstvi za poviševanje aktivnosti, kot so npr. olja, aditivi-organska topila in/ali površinsko aktivna sredstva. Posebno pri uporabi herbicidov, ki vsebujejo karbamoil fenil karbamat morajo dodati izjemno velike količine teh aditivov, da dosežejo zadostno biološko učinkovitost.Due to the above, the particles of the insoluble active ingredient must be ground into powder with maximum fineness, and their penetration and translocation properties should be improved by means of activity enhancers such as e.g. oils, additives-organic solvents and / or surfactants. Particularly when using herbicides containing carbamoyl phenyl carbamate, they must add extremely large quantities of these additives in order to achieve sufficient biological efficacy.
Mletje izvedejo z uporabo mlinov na zračni curek in suspenzijskih mlinov, zato da dobijo aktivne sestavine z maksimalno finostjo, prednostno velikosti 1-5 /im, da zagotovijo biološki učinek. Finost je prav tako potrebna za zagotovitev permanentnih suspenzij, izboljšane stabilnosti shranjevanja suspenzijskih koncentratov in izboljšanih suspenzijskih lastnosti za suspendirane granule.The milling is carried out using air-jet mills and suspension mills in order to obtain active ingredients with maximum fineness, preferably sizes 1-5 / im, to provide a biological effect. Fineness is also required to provide permanent suspensions, improved storage stability of suspension concentrates and improved suspension properties for suspended granules.
Angleška patentna objava GB 998264 npr. prikazuje, da etoksilirani maščobni amini izboljšajo absorpcijo določenih herbicidov, kot npr. paragvata in glifozata na listih. Vendar pa je značilna neugodnost etoksiliranih maščobnih aminov, želiranje v vodi, s čimer se zmanjša njihova sposobnost raztapljanja površinskih voskov lista, tako penetracija herbicidov ni optimalna. Po drugi strani povečana količina površinsko aktivnih sredstev lahko zviša fitotoksične lastnosti, ki poškodujejo gostiteljsko rastlino. Poleg tega so ti etoksilirani maščobni amini ekstremno hidrofilni, s čimer jim primanjkuje lastnost, ki jo prinese lipofilnost, t.j. povečana penetracija herbicida skozi voščeno plast lista. Hidrofilna površinsko aktivna sredstva, npr. maščobni amini, so torej zlasti prikladna le kot aditivi za hidrofilne aktivne sestavine, kot sta npr. paragvat in glifozat.English Patent Publication GB 998264 e.g. shows that ethoxylated fatty amines enhance the absorption of certain herbicides, such as e.g. paraguat and glyphosate on leaves. However, it is characterized by the disadvantage of ethoxylated fatty amines, gelling in water, thereby reducing their ability to dissolve the surface waxes of the leaf, so penetration of herbicides is not optimal. On the other hand, an increased amount of surfactants can increase the phytotoxic properties that damage the host plant. In addition, these ethoxylated fatty amines are extremely hydrophilic, thus lacking the lipophilic property, i.e. increased penetration of the herbicide through the wax layer of the leaf. Hydrophilic surfactants, e.g. fatty amines are therefore particularly suitable only as additives for hydrophilic active ingredients, such as e.g. paraguat and glyphosate.
Nadalje je iz evropske patentne objave EP 0 257 686 znano, da etoksi propoksi monoamini lahko izboljšajo biološko učinkovitost herbicidov. Maščobni amini ali maščobni amido amini/imidazolini, tvorjeni s tem sredstvom, ki povišuje aktivnost, vsebujejo vsaj en višji ostanek z 8-22 C, vezan na enega ali več atomov dušika.Furthermore, it is known from European Patent Publication EP 0 257 686 that ethoxy propoxy monoamines can improve the bioavailability of herbicides. Fatty amines or fatty amido amines / imidazolines formed by this activity-enhancing agent contain at least one higher residue of 8-22C attached to one or more nitrogen atoms.
Molekulska masa sredstva, ki povišuje aktivnost, naj bi bila manj kot 2500.The molecular weight of the activity enhancing agent is thought to be less than 2500.
Mednarodna patentna prijava WO 91/13546 nadalje uči, kako uporabiti etoksi propoksilirane blok kopolimere v obliki vodotopnih toplotno aktivnih vezivnih sredstev, kot aditivov za granuliranje.International Patent Application WO 91/13546 further teaches how to use ethoxy propoxylated block copolymers in the form of water-soluble heat-active binders as granulating additives.
Objava EP prijave 417 896 prikazuje pesticidni sestavek, ki vsebuje v vodi netopen pesticid in površinsko aktivno sredstvo. Površinsko aktivno sredstvo sestoji iz polietoksiliranega poli(etilen) amina ter estra poliola in C16-C22-nenasičene alifatske kisline.EP publication 417 896 discloses a pesticidal composition containing a water-insoluble pesticide and a surfactant. The surfactant consists of polyethoxylated poly (ethylene) amine and a polyol ester and C 16 -C 22- unsaturated aliphatic acid.
Namen predloženega izuma je zagotoviti izboljšan herbicidni sestavek.The purpose of the present invention is to provide an improved herbicidal composition.
Namen predloženega izuma je predvsem zagotoviti izboljšano sredstvo, ki zvišuje aktivnost za povečevanje učinkovitosti aktivne sestavine herbicida. Da bi dosegli zgornje namene je herbicidni sestavek v smislu predloženega izuma označen s tem, da herbicid vsebuje vsaj eno sredstvo, ki zvišuje aktivnost, ki je tetraalkoksiliran alkil diamin. Učinkovitost sredstva, ki zvišuje aktivnost lahko prednostno izboljšamo na sinergističen način z etoksi propoksi blok kopolimerom. Presenetljivo smo ugotovili, da tetraalkoksilirani alkil diamini s splošno formuloIt is an object of the present invention to provide an improved activity enhancer for increasing the potency of the active ingredient of the herbicide. In order to achieve the above purposes, the herbicidal composition of the present invention is characterized in that the herbicide contains at least one activity enhancer that is tetraalkoxylated alkyl diamine. The efficiency of the activity-enhancing agent can preferably be improved in a synergistic manner with the ethoxy propoxy block copolymer. Surprisingly, tetraalkoxylated alkyl diamines of the general formula were found
v kateri je n = 1-6, A Bin which n = 1-6, A B
R., Ro, Rq in R„ = - (CiU-CH-0) - (cfk-CH-O) - H,R., R o , R q and R '= - (CiU-CH-O) - (cfk-CH-O) - H,
2 J 4 2 p 2 q p+q = 5-150, in v kateri je ena od sestavin A in B vodik in je druga metilna ali etilna skupina, ki imajo molekulsko maso približno 1000 - 40000, znatno povečajo biološko učinkovitost pred tem omenjenih benzofuranskih, bipiridinskih, hidroksibenzonitrilnih, karbamoil fenil karbamatnih, piridazinskih, kinolinskih, sulfonil sečninskih in triazinskih herbicidov na plevelih.2 J 4 2 p 2 q p + q = 5-150, and in which one of the constituents A and B is hydrogen and the other is a methyl or ethyl group having a molecular weight of about 1000 - 40000, significantly increase the bioavailability of the previously mentioned benzofuran, bipyridine, hydroxybenzonitrile, carbamoyl phenyl carbamate, pyridazine, quinoline, sulfonyl urea and triazine weeds.
Zgoraj omenjena sredstva, ki povišujejo učinkovitost, so površinsko aktivna sredstva, za katera smo ugotovili, da imajo izjemno lastnost povečevanja biološke učinkovitosti benzofuranskih, bipiridinskih, hidroksibenzonitrilnih, karbamoil fenil karbamatnih, piridazinskih, kinolinskih, sulfonil sečninskih in triazinskih herbicidov, ki je na splošno bolj očitna kot je običajno pri drugih površinsko aktivnih sredstvih, uporabljenih v herbicidih. Nadalje smo ugotovili, da ta in nekatera druga površinsko aktivna sredstva delujejo sinergistično, pri čemer povečujejo biološko učinkovitost herbicidov bolj kot pričakujemo od seštevka učinkov teh površinsko aktivnih sredstev.The aforementioned performance enhancers are surfactants that have been found to have the remarkable property of enhancing the bioavailability of benzofuran, bipyridine, hydroxybenzonitrile, carbamoyl phenyl carbamate, pyridazine, quinoline, sulfonyl urea and triazine herbicides, which is more common obvious as is usual with other surfactants used in herbicides. We further found that these and some other surfactants act synergistically, enhancing the bioavailability of herbicides more than expected from the sum of the effects of these surfactants.
Za alkoksilirane diamine v smislu predloženega izuma se je izkazalo, da so posebno učinkoviti pri izboljševanju učinkovitosti herbicidov na škodljivih plevelih, kot npr. metliki (Chenopodium album), kačji dresni (Polygonum spp.), nedišeči trirobki (Matricaria inodorum), lakoti (Galium spurium) in navadni repi (Brassica napus).The alkoxylated diamines of the present invention have been shown to be particularly effective in improving the efficacy of herbicides in harmful weeds, such as e.g. butterflies (Chenopodium album), dragonfly (Polygonum spp.), nondescript tribrics (Matricaria inodorum), famines (Galium spurium) and common tails (Brassica napus).
Molekulska masa sredstva v smislu predloženega izuma , ki zvišuje učinkovitost, je prednostno 4000 - 25000, pri čemer velikost molekule ne omejuje njegove učinkovitosti, posebno na metliki.The molecular weight of the enhancing agent of the present invention is preferably 4000 - 25000, wherein the size of the molecule does not limit its effectiveness, especially on a broom.
Istočasno smo ugotovili, da etoksilirani propoksilirani blok kopolimeri, katerih molekulska masa je približno 2000 - 20000, prednostno 10000 - 18000, delujejo sinergistično s tetraalkoksiliranimi alkil diamini na navadni repi (Brassica napus), ki predstavlja plevel s precejšnjo plastjo voska na površinah njihovih listov. Hidrofilnost in biološki učinek teh blok kopolimerov na navadni repi narašča z maso molekule. Torej je po drugi strani možno, da se zaradi lipofilnosti tetraalkoksiliranih alkil diaminov v smislu predloženega izuma raztopi površinski vosek listov in poveča penetracija in se po drugi strani, zaradi hidrofilnosti etoksi propoksi blok kopolimerov nadalje povečuje penetracija/translokacija.At the same time, we have found that ethoxylated propoxylated block copolymers, whose molecular weight is about 2000 - 20000, preferably 10000 - 18000, act synergistically with tetraalkoxylated alkyl diamines on ordinary beets (Brassica napus), representing weeds with a considerable layer of wax on the surfaces of their leaves. The hydrophilicity and biological effect of these block copolymers on ordinary tails increases with the mass of the molecule. Thus, on the other hand, it is possible that due to the lipophilicity of the tetraalkoxylated alkyl diamines of the present invention, the surface wax of the leaves is dissolved and penetration is increased, and penetration / translocation is further enhanced by the hydrophilicity of the ethoxy propoxy block copolymers.
Sredstva v smislu predloženega izuma, ki povišujejo aktivnost, t.j. tetraalkoksilirani diamini in etoksi propoksilirani blok kopolimeri, ki vsi povečujejo biološko učinkovitost navedenih aktivnih sestavin, lahko dodamo v pršilni tank kot ločene zmesi v tanku, ki povišujejo aktivnost ali prednostno, vključene v formulacijo samo. Če je uporabljen herbicid v tekoči obliki, sredstva, ki zvišujejo aktivnost, lahko zmešamo s tekočo fazo. Pri uporabi trdnih herbicidov, lahko tekoča sredstva, ki zvišujejo aktivnost, absorbiramo v nosilce, tista v trdni obliki pa lahko uvedemo direktno v herbicidno maso. Sredstva, ki zvišujejo aktivnost, so lahko v obliki ločenih granul v trdnih herbicidih ali so lahko vgrajena v iste granule z aktivnimi sestavinami herbicidov.The activity enhancing agents of the present invention, i.e. tetraalkoxylated diamines and ethoxy propoxylated block copolymers, all of which increase the bioavailability of said active ingredients, can be added to the spray tank as separate mixtures in the activity enhancing tank or preferably included in the formulation alone. If a herbicide is used in liquid form, the activity-enhancing agents can be mixed with the liquid phase. When solid herbicides are used, liquid activity enhancing agents can be absorbed into the carriers, and those in solid form can be introduced directly into the herbicidal mass. Activity-enhancing agents may be in the form of separate granules in solid herbicides or may be incorporated into the same granules with the active ingredients of the herbicides.
Herbicidi v smislu izuma pa so sicer formulirani na običajen način. Aktivne sestavine so raztopljene v vodi ali organskih topilih, suspendirane v nosilni tekočini ali formulirane v trdni obliki. Na splošno vsebujejo približno 5-80% aktivnih sestavin. Voda, olje ali zmesi olja in vode so na splošno uporabljeni kot nosilne tekočine v suspenzijskih koncentratih. Površinsko aktivna sredstva (anionska, kationska, neionska ali amfolitična) običajno uporabimo, da zagotovimo in izboljšamo emulzibilnost, dispergirnost, stabilnost suspenzije, omočljivost, penetracijo in translokacijo in, da emulgiramo olje v dejanski koncentrat in zagotovimo mešljivost in stabilnost suspenzije/emulzije v končni raztopini. Pripravki lahko vključujejo druge aditive, kot npr. z vodo mešljive in/ali v vodi topne nosilce in/ali deflokulacijska sredstva, kot npr. kaolinske ali ligninske spojine, sredstva proti penjenju (npr. sredstva na osnovi silikona), zgoščevalna sredstva, kot npr. celulozne derivate, sredstva proti zmrzovanju v vodnih suspenzijah, kot npr. propilenglikol, organska topila, kot kerozin in sredstva za obarvanje. Poleg tega lahko uporabimo varovalna sredstva, npr. formalin, posebno če pripravek vsebuje organska suspendirna ali zgoščevalna sredstva. V primeru omočljivih granul in pelet lahko uporabimo kot nosilce inertne anorganske (npr. silicijeve kisline, soli) ali organske (npr. celuloza, poliakrilati, sečnina) spojine, da razredčimo aktivne sestavine ali adsorbiramo tekoča sredstva.The herbicides of the invention are, however, formulated in a conventional manner. The active ingredients are dissolved in water or organic solvents, suspended in a carrier fluid or formulated in solid form. They generally contain about 5-80% of the active ingredients. Water, oil or mixtures of oil and water are generally used as carrier liquids in suspension concentrates. Surfactants (anionic, cationic, nonionic, or ampholytic) are commonly used to provide and improve emulsivity, dispersibility, suspension stability, wettability, penetration, and translocation, and to emulsify the oil into the actual concentrate and to provide suspension / emulsion stability and stability in the final solution. . The preparations may include other additives such as e.g. water-miscible and / or water-soluble carriers and / or deflocculating agents, such as e.g. kaolin or lignin compounds, antifoaming agents (e.g. silicone based agents), thickening agents such as e.g. cellulose derivatives, antifreeze agents in aqueous suspensions such as e.g. propylene glycol, organic solvents such as kerosene and colorants. In addition, protective means may be used, e.g. formalin, especially if the preparation contains organic suspending or thickening agents. In the case of wettable granules, pellets can be used as carriers of inert inorganic (e.g. silicic acid, salts) or organic (e.g., cellulose, polyacrylates, urea) compounds to dilute the active ingredients or adsorb liquid agents.
Aktivne sestavine herbicidnih formulacij v trdni obliki so prednostno zelo fino zmlete, na velikost delcev, manjšo kot 10 μτη, prednostno 1-3 μπι. Mletje suhe mase izvedemo z uporabo npr. mlina na zračni curek, mletje suspenzij pa z uporabo mlina na bisere. Formuliranje suspenzijskih koncentratov izvedemo v reaktorju z učinkovitim mešanjem, granule ali pelete pa izdelamo z znanimi tehnikami, npr. z uporabo granuliranja z diski, pršilnim sušenjem, granuliranja s fluidizirano blazino, granuliranja z mešanjem z uporabo vertikalnega mešalnika ali mešalnika z lopatico in z granuliranjem z ekstruzijo, s stiskanjem, s centrifugiranjem, s pr silno plastjo ali pršilnim/ohlaj evalnim gr anuliranj em.The active ingredients of the solid form herbicidal formulations are preferably very finely ground, to a particle size of less than 10 μτη, preferably 1-3 μπι. Dry mass milling is carried out using e.g. air jet mill and grinding the suspensions using a pearl mill. The formulation of suspension concentrates is carried out in an efficient stirring reactor, and granules or pellets are prepared by known techniques, e.g. using disk granulation, spray drying, fluidized bed granulation, blending by blending using a vertical mixer or a spatula mixer, and granulating by extrusion, compression, centrifugation, a spray layer, or a spray / cooling grill.
Masno razmerje količin sredstev, ki povišujejo aktivnosti, proti količinam aktivnih sestavin v formulacijah je npr. od 15:1 do 1:2, prednostno od 5:1 do 1:1. Optimalno masno razmerje alkoksiliranega diamina proti etoksi propoksi blok kopolimeru v pršilu za navadno repo je od 1:2 do 1:4. V pršilih za metliko pa je bolj prednostno, da uporabimo večjo količino alkoksiliranega diamina. Torej je masno razmerje v pršilih za metliko lahko v območju prednostno od 10:1 do 1:10.The weight ratio of the amounts of activity enhancing agents to the amounts of active ingredients in the formulations is e.g. from 15: 1 to 1: 2, preferably from 5: 1 to 1: 1. The optimal weight ratio of alkoxylated diamine to ethoxy propoxy block copolymer in ordinary turnip spray is from 1: 2 to 1: 4. In broom sprays, however, it is more preferred to use a larger amount of alkoxylated diamine. Therefore, the mass ratio in the broom spray can preferably be in the range of 10: 1 to 1:10.
Poleg zgoraj navedenega, lahko s suspenzijskim koncentratom, granulami/peleti ali končno raztopino zmešamo tudi druge biocide in gnojila. Drugi biocidi vključujejo npr. druge herbicide, kot npr. acetamid, difenil eter, organofosfor, piridin, tiokarbamat, triazin in uracilne herbicide, sredstva za kontrolo bolezni rastlin, insekticide in regulatorje rasti. Zato, da povečamo spekter kontrole, je prednostno, da uporabimo za sladkorno peso ipd. zlasti substance, kot npr. lenacil, metolaklor, tri klor ocetno kislino, EPTC, cikloat, klopiralid, fluroksipir, benztiazuron, klorprofam, fenuron, izokarbimid, profam, trifluralin, aloksidimnatrij, setoksidim, cikloksidim, dialat, fluazifob-butil, trialat, dalapon, propankizafop, diklofop-metil, fenoksapropetil, kizalofopetil, haloksifopetoksi etil, in proksimfam poleg zgoraj navedenih sredstev.In addition to the above, other biocides and fertilizers can be mixed with the suspension concentrate, granules / pellets or final solution. Other biocides include e.g. other herbicides, such as acetamide, diphenyl ether, organophosphorus, pyridine, thiocarbamate, triazine and uracil herbicides, plant disease control agents, insecticides and growth regulators. Therefore, in order to increase the control spectrum, it is preferable to use sugar beet and the like. in particular substances such as e.g. lenacyl, metolachlor, three chlorine acetic acid, EPTC, cycloate, clopyralid, fluroxypyr, benzthiazuron, chlorpropham, fenuron, isocarbimide, profam, trifluralin, alloxydimnate, setoxidim, cyclooxidim, dialate, fluazifobapophyl butyl, triazolobenzophenyl butyl , phenoxapropethyl, kizalofopetyl, haloxyfopetoxy ethyl, and proximpham in addition to the above agents.
Predloženi izum je bolj podrobno opisan v nadaljevanju s primeri.The present invention is described in more detail below with examples.
Biološko učinkovitost herbicidov določimo v rastlinjaku s testi v lončkih. Pogoje za ustaljeno temperaturo, vlago in osvetljenost vzdržujemo v rastlinjaku avtomatsko. Na splošno testne rastline vključujejo plevele, ki povzročijo precej škode v nasadih sladorne pese ipd., kot npr. metliko (Chenopodium album = C. album) in navadno repo (Brassica napus = B. napus), ki odstopajo ena od druge glede na površinsko morfologijo njihovih listov in na ta način predstavljajo različne tipe plevelov. V testih smo tudi uporabili enoletni golšec Mercurialis annua (= M. annua) pri testiranju benzofuranskih herbicidov; nedišečo trirobko, t.j. Matricaria inodorum (= M. inodorum), ki je občutljiva na triazine in piridazine; navadni slakovec, t.j. Polygonum convolvulus (= P. convolvulus) smo uporabili za testiranje bipiridinov, hidroksibenzonitrilov in sulfonil sečnin, lakoto, tj. Galium spurium (= G. spurium) pa za kinoline in sulfonil sečnine. Občutljivost kultiviranih rastlin na poškodbo s herbicidi določimo z uporabo sadik sladkorne pese (Beta vulgaris).The biological effectiveness of the herbicides is determined in the greenhouse by pot tests. Conditions for stable temperature, humidity and illumination are maintained automatically in the greenhouse. In general, test plants include weeds that cause considerable damage in sugar beet plantations, etc. broom (Chenopodium album = C. album) and common turnip (Brassica napus = B. napus), which differ from each other in terms of the surface morphology of their leaves, thus representing different types of weeds. In the tests, we also used a one-year-old husk of Mercurialis annua (= M. annua) when testing benzofuran herbicides; the non-tangible triplet, i.e. Matricaria inodorum (= M. inodorum), which is sensitive to triazines and pyridazines; ordinary slacker, i.e. Polygonum convolvulus (= P. convolvulus) was used to test for bipyridines, hydroxybenzonitriles, and sulfonyl ureas; Galium spurium (= G. spurium) for quinoline and sulfonyl urea. The susceptibility of cultivated plants to herbicide damage is determined using beet seedlings (Beta vulgaris).
Pri testu na splošno uporabimo 5-8 sadik/rastlino-lonček in 3-5 lončkov v paralelki. Količina vode je 200 1/ha, nanašanje pa izvedemo z avtomatičnim dozirnim pršilnikom, ko so pleveli v stanju približno dveh listov. Končno določitev učinkovitosti herbicida naredimo 13-15 dni po pršenju.For the test, 5-8 seedlings / plant-pot and 3-5 pots in parallel are generally used. The amount of water is 200 l / ha and the application is carried out with an automatic dosing sprayer when the weeds are in the state of about two leaves. Final determination of herbicide efficacy is made 13-15 days after spraying.
V spodnjih rezultatih je učinkovitost izražena kot suha ali sveža masa nadzemeljskih delov plevelov ali kultiviranih rastlin na lonček ali na sadiko.In the results below, efficiency is expressed as the dry or fresh mass of the above-ground parts of weeds or cultivated plants per pot or seedling.
PRIMER 1EXAMPLE 1
Test lahko uporabimo zato, da prikažemo, da je alkoksiliran diamin (molekulska masa, mol.m.=6700) v smislu izuma očitno bolj učinkovit kot pred tem znani etoksilirani amini lojeve maščobne kisline (EO 15,20 in 30).The test can be used to show that the alkoxylated diamine (molecular weight, mol.m. = 6700) of the invention is clearly more effective than the previously known ethoxylated fatty acid amines (EO 15,20 and 30).
Suspenzijo aktivne sestavine pripravimo iz 80% fenmedifam granul, suspendiranih v vodi. Diamin v smislu izuma kot tudi amine lojeve maščobne kisline zmešamo kot aditive zmesi v tanku s suspenzijo aktivne sestavine.The active ingredient suspension is prepared from 80% phenmedipham granules suspended in water. The diamine of the invention as well as the amine fatty acid compound is mixed as additives of the mixture in a tank with a suspension of the active ingredient.
Količina fenmedifama = 720 g/haFenmedifam amount = 720 g / ha
Sredstvo, ki povišuje aktivnostAn activity that enhances activity
1. brez sredstva za povišanje aktivnosti1. without activity enhancement means
2. alkoksiliran diamin (mol.m.=6700)2. alkoxylated diamine (mol.m. = 6700)
3. etoksiliran amin lojeve maščobne kisline (E0=15)3. Fatty acid ethoxylated amine (E0 = 15)
4. etoksiliran amin lojeve maščobne kisline (E0=20)4. Fatty acid ethoxylated amine (E0 = 20)
5. etoksiliran amin lojeve maščobne kisline (E0=30)5. Fatty acid ethoxylated amine (E0 = 30)
6. komercialni pripravek Armoblen T/25, etoksiliran amin lojeve maščobne kisline (E0=15)6. commercial preparation Armoblen T / 25, ethoxylated fatty acid tallow amine (E0 = 15)
PRIMER 2EXAMPLE 2
V tem testu študiramo različne alkoksilirane diamine (mol.m. = 3600, 6700, 7500 in 12000). Ugotovili smo, da se učinkovitost izboljša, če je molekulska masa nad 3600 in neke vrste optimum dosežemo, če je molekulska masa približno 7000. Količina fenmedifama = 720 g/ha Priprava pršila kot v primeru 1.In this test, different alkoxylated diamines (mol.m. = 3600, 6700, 7500, and 12000) are studied. We have found that the efficiency is improved when the molecular weight is above 3600 and some optimum is achieved if the molecular weight is about 7000. Amount of phenmedipham = 720 g / ha Spray preparation as in Example 1.
(mol.m.=12000)(mol.m. = 12000)
PRIMER 3EXAMPLE 3
Iz testa je razvidno, da tako 1 kg/ha alkoksiliranega diamina (mol.m. = 6700) in 1 kg/ha etoksi propoksi blok kopolimera (mol.m. = 4150) daje nivo učinkovitosti, ki se ne da dosti bolj izboljšati na B.napus, celo če doziranje podvojimo. Alkoksiliran diamin (mol.m. = 6700) je bolj učinkovit kot etoksi propoksi blok kopolimer (mol.m. = 4150), posebno na Cehnopodium album, na Brassica napus pa opazimo sinergijo z zmesjo 20% + 80% (alkoksiliran diamin + etoksi propoksi blok kopolimer). Zmes alkoksiliranega diamina in etoksi propoksi blok kopolimera je bolj učinkovita kot ustrezna zmes etoksiliranega amina lojeve maščobne kisline in etoksi propoksi blok kopolimera. Alkoksiliran diamin (mol.m. = 6700) je bolj učinkovit kot etoksi propoksi blok kopolimer, posebno proti Chenopodium album.The test shows that both 1 kg / ha of alkoxylated diamine (mol.m. = 6700) and 1 kg / ha of ethoxy propoxy block copolymer (mol.m. = 4150) give a level of efficiency that cannot be improved much further. B. napus even if the dosage is doubled. Alkoxylated diamine (mol.m. = 6700) is more effective than ethoxy propoxy block copolymer (mol.m. = 4150), especially on Cehnopodium album, and on Brassica napus synergy with a mixture of 20% + 80% (alkoxylated diamine + ethoxy propoxy block copolymer). A mixture of alkoxylated diamine and ethoxy propoxy block copolymer is more effective than a suitable mixture of ethoxylated fatty acid tallow amine and ethoxy propoxy block copolymer. Alkoxylated diamine (mol.m. = 6700) is more effective than ethoxy propoxy block copolymer, especially against Chenopodium album.
Količina fenmedifama = 720 g/haFenmedifam amount = 720 g / ha
Priprava pršila kot v primeru 1.Spray preparation as in example 1.
PRIMER 4EXAMPLE 4
Iz testa je razvidno, da je zmes alkoksiliranega diamina (mol.m. = 6700) in etoksi propoksi kopolimera (mol.m. = 14000) sinergistična, posebno na Brassica napus. Iz testa je tudi razvidno, da je etoksiliran amin lojeve maščobne kisline (EO=15) manj učinkovit kot alkoksilirani diamini.The test shows that a mixture of alkoxylated diamine (mol.m. = 6700) and ethoxy propoxy copolymer (mol.m. = 14000) is synergistic, especially on Brassica napus. The test also shows that ethoxylated tallow fatty acid amine (EO = 15) is less effective than alkoxylated diamines.
Količina fenmedifama = 720 g/haFenmedifam amount = 720 g / ha
Priprava pršila kot v primeru 1.Spray preparation as in example 1.
Sredstvo, ki povišuje aktivnostAn activity that enhances activity
1. brez sredstva za povišanje aktivnosti1. without activity enhancement means
2. alkoksiliran diamin (mol.m. = 6700)2. alkoxylated diamine (mol.m. = 6700)
3. EO-PO blok kopolimer (mol.m. = 14000)3. EO-PO block copolymer (mol.m. = 14000)
4. EO-PO blok kopolimer (mol.m. = 14000) 75% + alkoksiliran diamin (mol.m. = 6700) 25%4. EO-PO block copolymer (mol.m. = 14000) 75% + alkoxylated diamine (mol.m. = 6700) 25%
5. etoksiliran amin (EO=15)5. ethoxylated amine (EO = 15)
PRIMER 5EXAMPLE 5
Iz testa je razvidno, da molekulska masa etoksi propoksi blok kopolimerov ni bistveno pomembna za učinkovitost.The test shows that the molecular weight of ethoxy propoxy block copolymers is not significantly important for efficiency.
Količina fenmedifama = 720 g/haFenmedifam amount = 720 g / ha
Priprava pršila kot v primeru 1.Spray preparation as in example 1.
PRIMER 6EXAMPLE 6
Iz testa je razvidno, da granule v smislu izuma, ki zvišujejo učinkovitost in sestojijo iz 70% etoksipropoksi blok kopolimera, 20% alkoksiliranega diamina in 10% dispergirnega sredstva precej povečujejo delovanje etofumezata in metamitrona. Iz testa je tudi razvidno, da imajo granule, ki jo povišujejo aktivnost, očitno boljši učinek kot običajni oljni emulgirni aditiv za povišanje učinkovitosti zmesi v tanku, imenovan Actipron (RP), in je komercialni pripravek, na študiranih plevelih (Chenopodium album, Matricaria inodorum, Mercurialis annua). Vendar učinkovita sestavina metamitron nima nobenega učinka na Mercurialis annua.The test shows that the performance enhancing granules of the 70% ethoxypropoxy block copolymer, 20% alkoxylated diamine and 10% dispersant significantly increase the activity of etofumesate and metamitron. The test also shows that activity-boosting granules have a clearly better effect than a conventional oil emulsifying additive to increase the effectiveness of a mixture in a tank called Actipron (RP) and is a commercial preparation on studied weeds (Chenopodium album, Matricaria inodorum , Mercurialis annua). However, the effective ingredient metamitron has no effect on Mercurialis annua.
Pripravek Aktivna sestavina (g/ha)Active ingredient preparation (g / ha)
Etofumesat 70% WG 400Ethofumesate 70% WG 400
Metamitron 80% WG (Goltix/Bayer) 360Metamitron 80% WG (Goltix / Bayer) 360
Etofumesat 20% EC (Kerniron/Kemira) 400Ethofumesate 20% EC (Kerniron / Kemira) 400
Pripravek pršila kot v primeru 1.Spray preparation as in example 1.
PRIMER 7EXAMPLE 7
Iz testa je razvidno, daThe test shows that
- ni upoštevanja vrednega nadaljnjega porasta v povečevanju učinka granul, ki povišujejo aktivost, če uporabljena količina presega 1 kg/ha,- there is no consideration for a further increase in enhancing the effect of activity-enhancing granules if the amount used exceeds 1 kg / ha,
- emulgirno olje, vgrajeno v granule, ki povišujejo aktivnost, nadalje izboljša učinkovitost, posebno proti Chenopodium album,- Emulsifying oil incorporated into activity-enhancing granules further improves performance, especially against Chenopodium album,
- etoksi propoksi monoamin, kot aditiv zmesi v tanku, ne poveča učinkovitosti granul, ki povišujejo aktivnost, na Chenopodium album in ima antagonističen učinek, znižuje učinkovitost na Brassica napus.- Ethoxy propoxy monoamine, as an additive of the mixture in the tank, does not increase the potency of the activity-enhancing granules on the Chenopodium album and has an antagonistic effect, reducing the potency on the Brassica napus.
Količina fenmedifama = 720 g/ha 80% fenmedifam granul in količina sredstva, ki povišuje aktivnost, je 1 ali 2 kg/ha granul, ki povišujejo aktivnost.The amount of phenmedipham = 720 g / ha 80% of the phenmedipham granules and the amount of activity enhancer is 1 or 2 kg / ha of activity enhancing granules.
PRIMER 8EXAMPLE 8
S tem testom raziskujemo lastnost zmesi iz treh deležev, ki sestoji iz fenmedifama (8%) + etofumezata (10%) + metamitrona (20%) v kombinaciji s sredstvom v smislu izuma, ki povišuje aktivnost. Iz rezultatov je razvidno, da je zmes alkoksiliranega diamina in etoksi propoksi blok kopolimera sinergistična. Optimalno masno razmerje zmesi, glede na obe vrsti plevela (C. album in B. napus), je približno 2:7. Testiran etoksi propoksi monoamin je očitno manj učinkovit kot zmes diamina in etoksi propoksi blok kopolimera na obeh plevelih.This test investigates the property of a three-part mixture consisting of phenmedipham (8%) + etofumesate (10%) + metamitron (20%) in combination with an activity enhancing agent of the invention. The results show that the mixture of alkoxylated diamine and ethoxy propoxy block copolymer is synergistic. The optimum mass ratio of the mixture with respect to both types of weeds (C. album and B. napus) is approximately 2: 7. The ethoxy propoxy monoamine tested is clearly less effective than a mixture of diamine and ethoxy propoxy block copolymer on both weeds.
Količine aktivnih sestavin so: fenmedifam 150 g/ha, etofumezat 190 g/ha in metamitron 180 g/ha. Granule aktivne sestavine suspendiramo v vodi 200 1/ha in dodamo sredstva, ki povišujejo aktivnost, v obliki bodisi granul ah tekočine.The amounts of the active ingredients are: phenmedipham 150 g / ha, etofumesate 190 g / ha and metamitron 180 g / ha. The active ingredient pellets are suspended in water 200 l / ha and activity enhancers are added in the form of either granules or liquids.
PRIMER 9EXAMPLE 9
Ločen etoksi propoksi monoamin, aditiv za zmes v tanku nadalje ne povečuje učinka granul, ki sestojijo iz zmesi iz treh deležev in sicer: fenmedifama (8%) + etofumezata (10%) + metamitrona (20%), dopolnjenih z granulami, ki povišujejo aktivnost, iz optimalne zmesi alkoksiliranega diamina in etoksi propoksi blok kopolimera (2:7). Dejansko dobimo očiten antagonističen učinek na Brassica napus.Separate ethoxy propoxy monoamine, the additive for the mixture in the tank does not further increase the effect of granules consisting of a mixture of three portions, namely: phenmedipham (8%) + ethofumesate (10%) + metamitron (20%) supplemented with increasing granules activity, from an optimal mixture of alkoxylated diamine and ethoxy propoxy block copolymer (2: 7). In fact, we have an obvious antagonistic effect on Brassica napus.
Količine aktivnih sestavin:Amounts of active ingredients:
fenmedifam 150 g/ha etofumezat 190 g/ha metamitron 380 g/haphenmedipham 150 g / ha etofumesate 190 g / ha metamitron 380 g / ha
Granule aktivnih sestavin suspendiramo v vodi, 200 1/ha in ločeno dodamo etoksi propoksi monoamin v tekoči obliki k pršilni raztopini pri 1 kg/ha.The active ingredient pellets were suspended in water, 200 l / ha and ethoxy propoxy monoamine in liquid form was added separately to the spray solution at 1 kg / ha.
PRIMER 10EXAMPLE 10
S tem testom primerjamo produkt v smislu izuma in tri produkte, ki so že na tržišču, za učinkovitost na plevelih. Istočasno primerjamo njihove učinke na gostiteljske rastline. V vseh primerih so aktivne sestavine v končnih raztopinah v obliki trdnih delcev, velikosti nekaj μτη in je končni produkt bodisi v obliki trdnih granul WG, ki se dajo suspendirati v vodi ali suspenzijskega koncentrata SC. Pripravek v smislu izuma vsebuje kot sredstvo, ki povišuje aktivnost 10% alkoksiliranega diamina + 35% etoksi propoksi blok kopolimera, kar ustreza 0,1 kg diamina in 0,35 kg blok kopolimera na hektar.This test compares a product of the invention with three products already on the market for weed efficiency. At the same time, we compare their effects on host plants. In all cases, the active ingredients in the final solutions are in the form of particulate matter, some μτη in size, and the final product is either in the form of solid WG granules which can be suspended in water or SC suspension concentrate. The composition of the invention contains, as an agent, an activity that increases the activity of 10% alkoxylated diamine + 35% ethoxy propoxy block copolymer, corresponding to 0.1 kg diamine and 0.35 kg block copolymer per hectare.
Celotna količina aktivnih sestavin v vseh primerih je 360 g/ha in količina vode 200 1/ha.The total amount of active ingredients in all cases is 360 g / ha and the amount of water is 200 1 / ha.
Iz testa je razvidno, da ima pripravek v smislu izuma očitno boljšo učinkovitost kot kompetentni produkti tako na metliki, tj. Chenopodium album kot tudi na navadni repi, t.j. Brassica napus in je škoda na gostiteljski rastlini, ki je sladkorna pesa, t.j. Beta vulgaris neznatna z vsemi študiranimi produkti.The test shows that the preparation according to the invention clearly has better efficacy than the competent products both on the broom, ie. Chenopodium album as well as ordinary tails, i.e. Brassica napus and is a damage to the host plant, which is sugar beet, i.e. Beta vulgaris insignificant with all products studied.
Pripravek Aktivna g suhe snovi/lončekPreparation Active g dry matter / crucible
Mentor Star SC/Pliiss-StaufferMentor Star SC / Pliiss-Stauffer
- fenmedifam 9,2%- fenmedifam 9.2%
- etofumešat 9,2%- etofumates 9.2%
- metamitron 27,1%- metamitron 27.1%
PRIMER 11EXAMPLE 11
S tem testom primerjamo učinkovitost granul v smislu izuma, ki povišujejo aktivnost, z učinkovitostjo amina lojeve maščobne kisline, komercialnega sredstva, ki povišuje aktivnost (Armoblen T/25) in oljnega emulgirnega komercialnega sredstva, ki povišuje aktivnost (Actipron) v različnih herbicidih. Za omenjene herbicide izberemo prikladne plevele.This test compares the performance of activity-enhancing granules of the invention with that of tallow fatty acid, an activity-enhancing commercial agent (Armoblen T / 25) and an activity-enhancing oil emulsifying agent (Actipron) in various herbicides. For these herbicides we choose suitable weeds.
Granule v smislu izuma, ki povišujejo aktivnost, so sestavljene iz 70% EO-PO blok kopolimera, 20% alkoksiliranega diamina in 10% dispergirnega sredstva.The activity-enhancing granules of the invention consist of 70% EO-PO block copolymer, 20% alkoxylated diamine and 10% dispersant.
Študirani herbicidi glede na njihovo kemijsko družino, njihove aktivne sestavine, imena pripravkov in doziranja so naslednja:The herbicides studied according to their chemical family, their active ingredients, the names of the preparations and the dosage are as follows:
Test lahko uporabimo zato, da prikažemo, da trdne granule v smislu izuma, ki povišujejo aktivnost, izboljšajo biološko učinkovitost pripravkov navedenih v primeru, vsaj tako dobro kot kontrolna tekoča sredstva Armoblen T/25 in Actipron, ki povišujeta aktivnost, kadar je aktivna sestavina bromoksinil, kloridazon ali triasulfuron. Delovanje drugih aktivnih sestavin se opazno poveča s trdnimi granulami v smislu izuma, ki povišujejo aktivnost, če primerjamo z zmesmi brez sredstva, ki povišujejo aktivnost in skoraj prav tako dobro kot s tekočimi sredstvi, ki povišujejo aktivnost.The assay can be used to show that the activity-enhancing solid granules of the invention improve the bio-efficacy of the preparations listed in the example, at least as well as the Armoblen T / 25 control agents and Actipron, which increase the activity when the active ingredient is bromoxynil , chloridazone or triasulfuron. The activity of other active ingredients is noticeably increased by the solid granules of the invention that increase activity when compared to mixtures without an activity enhancing agent and almost as well as liquid activity enhancing agents.
Pršilne zmesi pripravimo z mešanjem pripravkov v zgoraj navedenih količinah s količino vode, ki ustreza 2001/ha, kot sredstvo, ki povišuje aktivnost pa dodamo 1 kg granul, ki povišujejo aktivnost, 11 Armoblena T/25 ali 11 Actiprona na hektar.The spray mixtures are prepared by mixing the preparations in the above amounts with an amount of water corresponding to 2001 / ha, and 1 kg of activity-enhancing granules, 11 Armoblen T / 25 or 11 Actipron per hectare, are added as the activity-enhancing agent.
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Country | Link |
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EP (1) | EP0711112A1 (en) |
JP (1) | JPH09500892A (en) |
BG (1) | BG100317A (en) |
CA (1) | CA2168251A1 (en) |
CZ (1) | CZ25696A3 (en) |
EE (1) | EE9400099A (en) |
FI (1) | FI933374A (en) |
LT (1) | LT96006A (en) |
NO (1) | NO960346L (en) |
PL (1) | PL312780A1 (en) |
SI (1) | SI9400304A (en) |
SK (1) | SK12596A3 (en) |
WO (1) | WO1995003697A1 (en) |
YU (1) | YU48094A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5629260A (en) * | 1995-07-26 | 1997-05-13 | Basf Corporation | Heteric EO/PO block copolymers as adjuvants for herbicidal formulations |
AUPO405696A0 (en) | 1996-12-06 | 1997-01-09 | Ici Australia Operations Proprietary Limited | Herbicidal compositions |
GB0625591D0 (en) * | 2006-12-21 | 2007-01-31 | Agrovista Uk Ltd | Herbicide composition |
EP2090166A1 (en) * | 2008-02-14 | 2009-08-19 | Bayer CropScience AG | Liquid herbicidal preparations |
CN109169680A (en) * | 2018-09-14 | 2019-01-11 | 江苏好收成韦恩农化股份有限公司 | Herbicidal composition and preparation method thereof for Sugarbeet Fields |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1102206A (en) * | 1978-04-05 | 1981-06-02 | Osamu Umekawa | Microbicidal compositions for industrial use |
ES2021696B3 (en) * | 1986-08-20 | 1991-11-16 | Akzo Nv | HERBICIDES AND FUNGICIDES THAT CONTAIN ADDITIVES THAT STIMULATE ACTIVITY. |
US4954338A (en) * | 1987-08-05 | 1990-09-04 | Rohm And Haas Company | Microbicidal microemulsion |
FR2648316A1 (en) * | 1989-06-20 | 1990-12-21 | Rhone Poulenc Agrochimie | HERBICIDE COMPOSITIONS BASED ON N-PHOSPHONOMETHYLGLYCIN AND THEIR USE |
JPH0774124B2 (en) * | 1989-07-26 | 1995-08-09 | 竹本油脂株式会社 | Method for preparing water-based pesticide formulation composition and water-based pesticide formulation composition obtained by the method |
-
1993
- 1993-07-28 FI FI933374A patent/FI933374A/en not_active Application Discontinuation
-
1994
- 1994-07-27 CZ CZ96256A patent/CZ25696A3/en unknown
- 1994-07-27 SK SK125-96A patent/SK12596A3/en unknown
- 1994-07-27 PL PL94312780A patent/PL312780A1/en unknown
- 1994-07-27 WO PCT/FI1994/000331 patent/WO1995003697A1/en not_active Application Discontinuation
- 1994-07-27 CA CA002168251A patent/CA2168251A1/en not_active Abandoned
- 1994-07-27 JP JP7505601A patent/JPH09500892A/en active Pending
- 1994-07-27 YU YU48094A patent/YU48094A/en unknown
- 1994-07-27 EP EP94921670A patent/EP0711112A1/en not_active Ceased
- 1994-07-28 SI SI9400304A patent/SI9400304A/en unknown
- 1994-09-16 EE EE9400099A patent/EE9400099A/en unknown
-
1996
- 1996-01-26 NO NO960346A patent/NO960346L/en unknown
- 1996-01-26 LT LT96-006A patent/LT96006A/en unknown
- 1996-01-29 BG BG100317A patent/BG100317A/en unknown
Also Published As
Publication number | Publication date |
---|---|
FI933374A0 (en) | 1993-07-28 |
CZ25696A3 (en) | 1996-06-12 |
NO960346L (en) | 1996-03-26 |
JPH09500892A (en) | 1997-01-28 |
WO1995003697A1 (en) | 1995-02-09 |
NO960346D0 (en) | 1996-01-26 |
FI933374A (en) | 1995-01-29 |
CA2168251A1 (en) | 1995-02-09 |
LT96006A (en) | 1996-05-27 |
BG100317A (en) | 1997-03-31 |
YU48094A (en) | 1997-08-22 |
EE9400099A (en) | 1995-12-15 |
PL312780A1 (en) | 1996-05-13 |
SK12596A3 (en) | 1997-02-05 |
EP0711112A1 (en) | 1996-05-15 |
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