CS221819B2 - Herbicide means - Google Patents

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CS221819B2
CS221819B2 CS81652A CS65281A CS221819B2 CS 221819 B2 CS221819 B2 CS 221819B2 CS 81652 A CS81652 A CS 81652A CS 65281 A CS65281 A CS 65281A CS 221819 B2 CS221819 B2 CS 221819B2
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Czechoslovakia
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align
active ingredient
hoř
substituted
compositions
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CS81652A
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Robert J Theissen
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Rhone Poulenc Inc
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    • C—CHEMISTRY; METALLURGY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
    • C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
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    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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Abstract

Compounds of formula <CHEM> that have pre and post emergence activity. The substituent A is such that they include certain substituted phenyl esters, phenyl thioesters, heterocyclic esters; substituted alkyl and alkylthio esters, carbonates and thiocarbonates; benzoyl phosphonates; substituted alkanones and substituted amides.

Description

Vrnález se týká herbicidních , prostředků obsahujících jako, účinnou složku určité substituóvané C2 až C, alkylestery 2-nitro-5-(substttuovaný fenoxy)benzoové kyseliny, které jsou popsány dále.The present invention relates to herbicidal compositions comprising, as an active ingredient, certain substituted C 2 -C C alkyl esters of 2-nitro-5- (substituted phenoxy) benzoic acid as described below.

Patenty US č. 3 652 645, 3 784 635, 3 873 302, 3 983 168 a 3 907 866 se týkají určitých derivátů fenoxyrbenzoooé kyseeiny, které‘jsou užitečné jako herbicidy. V souvislosti s vynálezem byly nyní nalezeny další deriváty fenoxybenzoové kyseliny, které jsou užitečné jako herbicidy.U.S. Pat. Nos. 3,652,645, 3,784,635, 3,873,302, 3,983,168, and 3,907,866 refer to certain phenoxybenzoic acid derivatives which are useful as herbicides. Other phenoxybenzoic acid derivatives useful as herbicides have now been found in connection with the invention.

Předmětem vynálezu je herbicidní prostředek, vyznač^ící se tím, že jako účinnou složku obsahuje sloučeninu obecného vzorce I .The present invention provides a herbicidal composition comprising as active ingredient a compound of formula (I).

(U kde ,(Where,

- *- *

R představuje alkylskupinu s 1 až 4 atomy uhlíku substituovanuu kyanoT, acceyl-, fenyl-, fenoxyfenny-, fenoxy, akry tyt, met^aky^i^-, nitro-, metthytf io-, met^^su^^!», meehulssSfinyl, methoxy- nebo etUuxysktpinut.R is C 1 -C 4 alkyl substituted with cyano T , acceyl, phenyl, phenoxyphenenes, phenoxy, acrylate, methyl, methyl, nitro, methylthio, methyl, methyl, phenoxy, phenyl, phenoxyphenyl, phenoxy, acrylate, methyl, phenyl, phenoxyphenyl, , methylsulfinyl, methoxy- or ethylsulfinyl.

Sloučeniny obecného vzorce I lze připravovat různými způsoby. Jeden způsob přípravy těchto sloučenin spočívá v appikaci Ullmanovy syntézy etherů reakcí alkalické (například sodné nebo draselné) sooi vhodně substituovanéUo fenolu, například m-lUldruxybenzaldeUydu nebo m-kresolu s reaktivní Ualogensubstituovanou aromatickou sloučeninou, například 34-dichlurbenzoUriftuorieem. Meeiprodukt, který se získá, se může nitrovat a dále . o sobě známým způsobem převádět na pří stáné b^r^nzobl^deri^i^l^y. Když se jako výchozí látky pouuije m-kresolu, může se získaný produkt oxidovat a pax nitrovat před tím než se převádí na pří stáné deriváty. Alternativně lze tyto sloučeniny získat odštěpením reaktivního halogenu (nappíklad v halogennakyt X) pomocí sooi kyseliny, nappíklad soLL obecného vzorceThe compounds of formula (I) may be prepared in various ways. One method for preparing these compounds is to apply Ullman ether synthesis by reacting an alkaline (e.g. sodium or potassium) salt of a suitably substituted phenol, e.g. The intermediate product obtained can be nitrated and further. in a manner known per se to the associated compounds. When m-cresol is used as the starting material, the product obtained can be oxidized and pax nitrated before being converted to the associated derivatives. Alternatively, these compounds can be obtained by cleavage of reactive halogen (e.g. in haloacyt X) with an acid salt, e.g.

II aryl—C — OK.II aryl — C - OK.

Byly připraveny tyto substiuuované C , až C , elkylestery charakte^^vené obecným vzorcem I:The following substituted C 1 to C 1 alkyl esters, characterized by formula (I):

Sloučenina číslo Compound number Suussituovaná alkylskupina Suussitized alkyl Teplota tání °C Melting point ° C 1 1 -CCC^^CN . -CCC ^^ CN. olej oil 2 2 -CHCC^JCN -CHCC ^ JCN olej oil 3 3 -CH2COCH3 -CH2COCH3 83 až 85 83 to 85 4 4 -CH^^ /Ho) -CH ^^ /Him) olej oil 5 5 — CH2—0) 0 - CH 2 -0) 0 olej oil 6 6 -CH2-CH2 - OC — CH- CH2 0 CH-CH 2 -CH 2 -OC-CH- CH 2 O CH olej oil 7 7 n 1 3 - CH2 -CH2-OC - C = CH2 n 1 3 -CH 2 -CH 2 -OC-C = CH 2 olej oil 8 8 -CH2-CH2-CN-CH 2 -CH 2 -CN olej oil

Tabulka - pokračováníTable - continued

Sloučenina číslo Compound number SubiSiluovaná alkyl skupina Substituted alkyl group Teplotá tání °CTemperature T ck C 9 9 cH2-cH2-o —cH 2 CH 2 O - 86 až 88 86 to 88 10 10 - cH2~ CH2—(q) - c H 2 - CH 2 - (q) 112 až 113 112 to 113 1 1 1 1 -CH2C(CH3)2-NO2 -CH 2 C (CH 3 ) 2 -NO 2 olejovitá polopevná látka, I. δ. C = 0 1 740 cm-1 oily semi-solid substance, I. δ. C = 0.174 0 cm -1 1 2 1 2 -CH2-CH2-SCH3 -CH 2 -CH 2 -CH 3 olej oil 13 13 -CH2-^CH2»SO2CH3 -CH 2 --CH 2 CH 2 SO 2 CH 3 97 až 99 97 to 99

Jako jiné sloučeniny z této třídy lze uvést tyto látky:Other compounds in this class include:

-CH,CN -сн“-с(осн3)2-снз -CH~-CHÍCH3)-^NO2 -CH2-CH(OC2 H5 )2 -CH -SO-CH, -CH2-CH2-SO-CH3 -CH2-S-CH3CH, CN -сн "-с (осн 3) 2 -CH снз -CHÍCH ~ 3) - ^ NO2 -CH 2 -CH (OC 2 H 5) -SO 2 -CH-CH, -CH2-CH2- SO-CH 3 -CH 2 -S-CH 3 olej, I. Č. C = 0, 1 725 cm- ’ 73 sž 74 olej, I. Č. C = 0, 1 740 cm-' 1 740 cm-1 115 až 118 I. Č. C == 0, 1 745 cm“ ' 113 až 115, I. C. C = 0, 1 745 cm1 olej, I. Č. C = 0, 1 740 c^1 oil, I. No. C = 0, 1 725 cm - 73 to 74 oil, I. No. C = 0, 1 740 cm - 1 740 cm -1 115 to 118 I. No. C == 0, 1745 cm -1 113-115, IC C = 0, 1745 cm 1 oil, I. No. C = 0, 1740 c ^ 1 SuliSituovant alkylskupina Sulfurizing alkyl group Název sloučeniny Name of the compound CH 0 I3 1CH 0 I 3 1 1-aceeylethyl-5-[2-chlor-4- -(tiilluormethrl)fenoxyy-2- 1-Aceeylethyl-5- [2-chloro-4- - (thiyl fluoromethyl) phenoxy-2- CH - CCH3 CH-CCH 3 -ni0oibenzoát -ni0oibenzoate 0 1 0 1 3-aceetrproolrl5- [2-chlor-4- -(trilluoemethrl)eenoxyl-2- 3-Aceetrprool-15- [2-chloro-4- - (trilluoemethrl) eenoxyl-2- CH2CH2CH2CCH3 CH2CH2CH2CCH3 -ni0oibenzott -ni0oibenzott 0 CH2CH2SCH3 0 CH2CH2SCH3 2- (mUt^l^ssuli ny i )eth^l-5- - [2-chlor-4-( trii luormethyri)f enoxyr-2-ni0oibenzoát 2- (mUt-1-sulfinyl) eth-1-5- - [2-chloro-4- (trifluoromethyl) phenoxy-2-nitro-benzoate

Pro dosažení herbicidního účinku se mohou ploučeniny podle vynálezu aplikovat různými způsoby. Mohou se aplikovat jako takové ve formě pevných látek nebo par, ale přednostně se jich používá jako toxických složek v herbicidních prostředcích obsahnjících tyto sloučeniny a nosič. Tyto prostředky se přednostně aplikují přímo na půdu a často se s ní mísí. Prostředky mohou mít formu granulátů, poprašů, kapalných poosřiků, aerosolových poosířiků a mohou obsahovat kromě nosiče přísady, jako jsou emulggtory, p^jjiva, plyny stlačéné do kapalného stavu, odoranty, stabilizátory apod.The compounds of the invention can be applied in various ways to achieve a herbicidal effect. They can be applied as such in the form of solids or vapors, but are preferably used as toxic components in herbicidal compositions comprising these compounds and a carrier. These compositions are preferably applied directly to the soil and often mixed with it. The compositions may take the form of granules, dusts, liquid sprays, aerosol sprays, and may contain, in addition to the carrier, additives such as emulsifiers, binders, compressed gases, odorants, stabilizers and the like.

Může se používat celé řady kapalných a pevných nosičů. Jako neomezzujcí příklady pevných nosičů lze uvést maatek, beetonit, křemelinu, pyrooflit, valchářskou hlinku·, sádrovec, moučku ze semen bavlníku a z ořechových skořápek s různé přírodní a syntetické jíly, které nemma! pH vyšší než asi 9,5. Jako ^οι^ή^οί příklady kapalných nosičů lze uvést vodu, organická rozpouštědla, jako alkoholy, ketony, amidy a estery, mi^í^rí^].ní oleje, jako petrolej, lehké oleje a střední oleje a rostlinné oleje, jako je olej z bavlníkových semen.A variety of liquid and solid carriers can be used. Non-limiting examples of solid carriers include maatek, beetonite, diatomaceous earth, pyrooflit, fuller clay, gypsum, cottonseed and nutshell flour with various natural and synthetic clays that they do not have! pH greater than about 9.5. Examples of liquid carriers include water, organic solvents such as alcohols, ketones, amides, and esters, mild oils such as kerosene, light oils and medium oils and vegetable oils such as is cottonseed oil.

V praxi se aplikované mnnžsSví herbicidu vyjadřuje v počtu kg herbicidu aplikvanném na 1 ha. Sloučeniny podle vynálezu jsou účinnými heebicidy, když se aplikují v mnnosSví od asi 0,2 do asi 10 kg/ha.In practice, the applied amount of herbicide is expressed in kg of herbicide applied per ha. The compounds of the invention are potent heebicides when applied at a rate of from about 0.2 to about 10 kg / ha.

PeeSicidní prostředky obsaahujcí účinnou složku a nosič se mohou dodávat bu3 jako hotové prostředky nebo jako konceenráty. Konicriráty obvykle obsahuJjí vyšší podlí účinné složky než prostředky pro okamžžté p^t^žSi^:í, a proto vySaddjí před použitím zředění. Jak hotové prostředky, tak konceenráty mohou být v kapalné nebo pevné formě, tj. účinná složka může být smíšena jak s kapalným, tak s pevným nosičem.The pesticidal compositions containing the active ingredient and the carrier may be supplied either as finished compositions or as endenates. Conicrates generally contain higher proportions of active ingredient than instantaneous formulations and therefore require dilution prior to use. Both the finished compositions and the endenates may be in liquid or solid form, i.e. the active ingredient may be mixed with both the liquid and the solid carrier.

Množsví účinné složky v prostředku závisí především na tom, zda prostředek je ' koncennrát nebo hotový prostředek pro okamžžté porUSií. Коп^^г^у obvykle obsehuuí 5 až 95 přednostně 10 až 80 % hmoonnotních účinné složky. Koncentrace účinné složky v prostředcích připravených k okamžitému po^iužtí závisí na způsobu aplikace konkrétního prostředku a na požadovaném stupni ršetření.-Porttřediy pro okamžžté potuští obvykle obsahnuí 0,001 až 1, přednostně 0,01 až 0,1 % hmoonootního účinné složky. Obecně tedy mohou prostředky obsahovat 0,001 až 95 % hžornorSnϊeh účinné složky, přičemž skutečné množní závisí na druhu prostředku - a na metodě, jakou se má aplikovat.The amount of active ingredient in the composition depends primarily on whether the composition is a concentrate or a ready-to-use composition. Typically, from about 5% to about 95%, preferably from about 10% to about 80%, of the active ingredient is present. The concentration of the active ingredient in the ready-to-use compositions will depend upon the method of administration of the particular composition and the degree of investigation desired. The instantaneous portions typically contain 0.001 to 1%, preferably 0.01 to 0.1%, of the hmoonoot active ingredient. Thus, in general, the compositions may contain from 0.001 to 95% of the active ingredient, depending on the nature of the composition - and the method to be employed.

K^r^n^c^ent^i^-ty mohou být bu3 kapalné nebo pevné a lze j= obvykle ře^ďt vodou za vzniku emmlz! nebo suspenzí obsaauuících žo^ší mιo0ství účinné složky. Alternativně lze kapalné nebo pevné konceenráty nastavovat kapalnými - nebo pevnými noosži za vzniku prostředků pro bezprostřední potušil. Kapalné konceenráty přednostně obsshuuí účinnou složku a ernougátor, který je rozpuštěn v kapalném rozpouštědle, například organickém rozpouštědle shora uvedeného typu. - Brnolgátor je účelně aniontový, kationtový nebo neiontový ^m^gú^T, například dodeeylbrozen8ulkontn sodný nebo adukt ethylenoxidu na alkyl^no!, oerkaptan, amin nebo karboxylovou kyselinu. Kapalné konceenráty s výhodou obsáhlí 10 až 30 % hmornnktníeh, například 25 % hžoknooSníeh účinné složky, například 1 kg účinné složky na 4 kg koncentrátu.The crystals may be either liquid or solid and can usually be diluted with water to form emulsions. or suspensions containing a greater amount of the active ingredient. Alternatively, liquid or solid endenates may be adjusted with liquid - or solid bearings to provide means for immediate appearance. The liquid endenates preferably contain the active ingredient and the emulsifier, which is dissolved in a liquid solvent, for example an organic solvent of the above type. The brominator is suitably anionic, cationic or non-ionic, for example sodium dodecylbenzoic acid or an ethylene oxide adduct to alkylphenol, omercaptan, amine or carboxylic acid. The liquid endenates preferably comprise 10 to 30% by weight, for example 25%, of the active ingredient, for example 1 kg of active ingredient per 4 kg of concentrate.

Sm0tčtrlné prášky jsou jinou přednostní formou kmceenrátu a tyto konceenráty účelně obsahtuí účinnou složku, jemně rozdělený pevný nosič a alespoň jednu povrchově aktivní látku, která dodává konceenrátu smžáitelnost a dispergovatelnost. Pevné nosiče vhodné pro přípravu tmOtčtrlnýeh prášků mohou být buá organické nebo anorganické. Vhodnými organickými nóssči jsou sojová moouka, moučka ze skořápek ořechů nebo dřevná moučka a tabákový prach a vhodnými anorganickými ooosčí jsou beniokit, ka^int nebo valchářské hlinky, oxidy křemičité, jako je křeme^na, silikáty, jako je matek, pyycoyyit nebo křemičitany - kovů alkaícckých zemin, dále u^l.ičiO^n^y vápníku a hořčíku.Emulsion powders are another preferred form of co-concentrate, and these concentrates conveniently comprise the active ingredient, a finely divided solid carrier, and at least one surfactant that imparts wettability and dispersibility to the concentrate. Solid carriers suitable for the preparation of dark-powdered powders may be either organic or inorganic. Suitable organic noodles are soybean meal, nutshell meal or wood flour and tobacco dust, and suitable inorganic oats are beniokite, caustic or fuller's earth, silicas such as quartz, silicates such as mothers, pyycoyyite or silicates. alkaline earth metals, furthermore calcium and magnesium.

Nooič může být jedna látka nebo se může jednat, o směs jemně rozmělněných pevných látek. Povrchově aktivní látka nebo jejich směs je obvykle příooona v množta! od 1 de 10- % hooonoo^ích, vztaženo na ад0М^1лу prášek. Vhodnými dispergátory jsou fkržэldrhydnntttlrosulfonan sodný nebo ligninsžlkonto sodný. Jako smžáedla lze uvést vyšší tliyltoyitžlOootty (kde vyšší alkyl” znamená alkyl obsa^u^í alespoň 8 atomů uhhíku), jako je dojeeylbeozeo^Ιί^!^ vápenatý, sulfáty alkoholů, rlkylrnnoJyethrxyethkχyethylsulkontoy sodná, dioktylsulfoeukcinát sodný, ethyleokxidkvé adukty s mastnými alkoholy, mastnými kyselinami nebo s vyššími alkyl^no^, jako je kktylrenoxypki.yethkxyethtnol.The carrier may be a single substance or may be a mixture of finely divided solids. The surfactant or mixture thereof is usually present in amounts. from 1 to 10% by weight of the composition, based on an aluminum powder. Suitable dispersants are sodium hydrosulfonate or sodium lignin. As the wetting agents, higher thiyltools (those wherein the higher alkyl means alkyl having at least 8 carbon atoms), such as sodium bisulfate, sodium sulphates, sodium alkyl, sodium dioctyl sulphate, sodium dioctyl sulphate, with acids or with higher alkyl groups such as ctylrenoxypolyethyloxyethanol.

Dále mohou tyto prostředky obsahovat látky zlepš^ící ulpívání a rozliv, jako je glyeeroloanoittnlturát nebo kondenzát po^g^c^Mu a olejové kyseeiny то^^кс^^у ^1^.hydrideo. Obsah účinné složky ve sožáčtelnéž prášku může být v rozmezí od 20 do 80 % hmotnostních, předno^í rozmezí koncentrace je však 50 až 80 % hmoknootníeh.In addition, the compositions may include adherence and leveling agents, such as glycerol mono-nitrate or condensate, and oleic acid acids. The active ingredient content of the wettable powder may range from 20 to 80% by weight, but preferably the concentration range is 50 to 80% by weight.

Popraše se mohou připravit tak, že se účinná složka smísí s pevným nosičem, jako je jemně rozdělený jíl, mmatek, oxid ·křemičitý a syntetické křemičitany, uhličitany kovů alkalických zem.n a ředidla přírodního původu, jako jp tabákový prach nebo moučka z ořechových skořápek. Granuláty lze vyrobit za pooUití pevných nosičů podobného typu pouze s tím rozdíeem, ie se používá nosičů s většími, částicemi v rozmezí od asi 246 do 1 080 /um. Do těchto pevných prostředků se může přidat menší mnlžsví .dispergačního činidla. Koncentrace účinné složky v těchto popraších nebo granulátech může být v rozmezí od 1 do 20 % hmolnoitnich. Pevné nosiče používané v těchto prostředcích mohou být v podstatě inertní nebo mohou být zčássi nebo úplně tvořeny hnnjivy, jako je síran amonný nebo jóné amonné soli, molovina, fosforečnany vápenaté, chlorid draselný nebo sušená krev.Dusts can be prepared by mixing the active ingredient with a solid carrier such as finely divided clay, talcum, silica and synthetic silicates, alkaline earth metal carbonates and diluents of natural origin such as tobacco dust or nutshell flour. Granules can be prepared using solid carriers of a similar type, except that carriers with larger particles in the range of about 246 to 1080 µm are used. A smaller amount of dispersant may be added to these solid compositions. The concentration of the active ingredient in these dusts or granules may range from 1 to 20% by weight. The solid carriers used in these compositions may be substantially inert, or may be partially or totally propellants such as ammonium sulfate or ammonium salts, urea, calcium phosphates, potassium chloride, or dried blood.

Jednou obzvlášť vhodnou metodou výroby pevných prostředků je zpracovat pevný nosič s účinnými složkami rozpuštěnými v rozpouštědle e nechat rozpouštědlo oddpait. Tak se získá nosič, obvykle ve formě jemně rozdělených čássic, které jsou napuštěny účinnými složkami. Jinou metodou j aplikovat směs účinných složek v rozaaveném stavu nebo postřikem.One particularly suitable method of making solid compositions is to treat the solid carrier with the active ingredients dissolved in the solvent and allow the solvent to evaporate. A carrier is thus obtained, usually in the form of finely divided particles which are impregnated with the active ingredients. Another method is to apply the active ingredient mixture in the molten state or by spraying.

Koncentrace účinné sležky v konečném prostředku určeném pro bezprostřední poiužtí nezávisí jen na požadovaném stupni aplikace (obvykle v rozmezí 0,2 až 10 kg/ha, jak je shora uvedeno) ale též na způsobu aplikace, kterého se má pouužt. SInOSiteloé prášky a kapalné kineeenréty se obvykle opUí^í jako vodné prostředky, přččemž stupeň aplikace kolísá od asi 10 do 1 500 1/ha. Při poouítí pozemního postřikového zařízení bývá stupeň aplikace obvykle v rozmezí·od 100 do 500 1/ha, zatímco při leeeckém pootřiku se obvykle používá mnlžsví 15 až 80 1/ha.The concentration of effective feed in the final ready-to-use composition depends not only on the desired application rate (usually in the range of 0.2 to 10 kg / ha as mentioned above) but also on the application method to be used. Solvable powders and liquid cine enemies are generally described as aqueous compositions, with application rates varying from about 10 to 1,500 l / ha. In the case of ground spray equipment, the application rate is usually in the range of from 100 to 500 l / ha, while the amount of application of the spray is usually 15 to 80 l / ha.

Zkoušky heřbicidní účinno^iTests of herbicidal efficacy

Způsob pěstování zkušebních rosslinMethod of growing test rosslin

Plodiny a plevelné rostliny se vysejí do fbboových misek pro jedno pooužtí o rozměrech 20,3 x 25,4 cm obsahuubcích půdu pro přesazování. V každé misce se vytvoří 10 cm řádka se všemi zkušebními rostlinami. Jako plodin · · se používá kukuřice (KU), rosičky krvavé ^^gre^ú (RK), bavlníku (BA) a sóji (SO). Plevelné druhý zeliímu* bér vlašský (BV), bér (BE), ab^ilm (AB), řepeň (ŘE), Učíci sareptskou (HS) a lhtkhvje ohnutý (pigweed) (LO).Crops and weeds are sown in single-use 20 x 25.4 cm single-use fbbo dishes containing soil for transplanting. A 10 cm row is created in each dish with all test plants. Corn (KU), bloody dew (RK), cotton (BA) and soybean (SO) are used as crops. Weed second cabbage (BV), beef (BE), ab ^ ilm (AB), beet (ŘE), sareptic (HS) and pigweed (LO).

Baavník, kuklice, sója a řepeň se vysé^aí v počtu 4 až 5 semen na řádku v závislosti na druhu. Druhy s menšími semeny (ОлПИю, hořčice ^rep^ká, laskavee ohnutý, bér vlašský a bér) se vysé^aí tak, že se počet semen nopplčtá, ale zaseje se dostatečný počet semen pro získání solidní řádky semenáčků.The loaf, soybean, soybean and beet are planted at 4-5 seeds per row, depending on the species. The smaller seed species (ллПИ, rep, rep hoř hoř rep, hoř hoř hoř hoř hoř rep rep rep hoř hoř rep rep rep hoř hoř hoř hoř rep hoř hoř hoř,,,,,,,,,,,,,,,,,,,, О,,,,,,,, О О О О О О О О О О О О О О О О О О О О О О О О О Оé vys vysé vys vys vys vys vys vys vys vys vys vys vysé vys vysé vys

Rokliny pro preemeegeenní i postemergeetní zkoušky se vyséwají stenným způsobem. První závlaha po vzeeití se aplikuje shora. Postemmegeenní fáze pěstování se pak provádí tak, aby se v době ošetřování získaly rostliny ve vhodném stadiu vývoje. Vzorky pro preemergentní fázi se připravují nejdříve jeden den před ošetřením.The gorges for both pre-and post-mortem tests are sown in the wall. The first after irrigation is applied from above. The post-mortem phase of cultivation is then carried out in such a way that at the time of treatment the plants are obtained at a suitable stage of development. Samples for the pre-emergence phase are prepared no earlier than one day before treatment.

Požadovaný stav vývoje v době po^me^e^ního ošetření je u širlillistýcU druhů (BA, SO, RK, AB, HS a LO) stadiím jednoho pravého listu nebo prvního trljheli0natéUl listu. Požadovaný stav vývoje u kukuřice je výška 7,6 až 10,2, zatímco u travin je to výška 5,1 cm.The desired state of development at the time of the post-treatment treatment in the broad-leaved species (BA, SO, RK, AB, HS, and LO) is the stages of one right leaf or first leaf leaf. The desired state of development for maize is 7.6 to 10.2, while for grass it is 5.1 cm.

Způsob ošetřeníMethod of treatment

Aplikace účinných látek se provádí pistříem ruční rozstřikovací pistolí aspiračního typu současně na jednu misku se vzrostlými rostlinami (postemeegeenní fáze) a jednu nově osetou misku (preemeegeennb fáze). Stupeň ošetření 1^2 kg/ha je představován rovnoměrnou o aplikací 116 mg zkušební sloučeniny na plochu obou misek dohromady ( 1 030 cm· ). Na poi^ik se používá roztoku účinné látky ve směěi rozpouštědel lbsahující 40 ml acetonu a 40 ml vody doplněné 0,1 % stláčela.The application of the active compounds is carried out by a pistol with an aspiration-type hand spray gun simultaneously on one bowl with mature plants (post-gegegenic phase) and one newly sown bowl (pre-geegeennb phase). A treatment rate of 1 - 2 kg / ha is represented by a uniform application of 116 mg of test compound to the surface of both trays together (1030 cm @ -1). A solution of the active compound in a solvent mixture containing 40 ml of acetone and 40 ml of water supplemented with 0.1% compressed water is used in the process.

Po postřiku se misky vrátí do skleníku. Do misek pro postemergentní zkoušku sé uvádí voda pouze zespodu. Do misek pro preemergentní fázi se přivádí voda kropením svrchu, dokud po ošetření nevzejdou rostliny. Další zavodňování se provádí zespodu.After spraying, the bowls are returned to the greenhouse. Water is only introduced from below into the post-emergence test dishes. Water is added to the preemergence phase dishes by sprinkling from above until the plants have emerged after treatment. Further irrigation is carried out from below.

Poškození a potlačení rostlin jak v případě preemergentních, tak v případě postemergentní ch zkoušek se hodnotí dva týdny po ošetření. Používá se stupnice 0 až 100 %. Do stupně poškození a potlačení se současně zahrnují též speciální fyziologické účinky.Plant damage and suppression in both pre-emergence and post-emergence tests are evaluated two weeks after treatment. A scale of 0 to 100% is used. Special physiological effects are also included in the degree of damage and suppression.

Hodno;,., herbicidní účinnosti pro sloučeniny 1 až 13 se získají při aplikaci 11,2 až 0,28 kg účinné sloučeniny na 1 ha. Výsledky jsou uvedeny v tabulce 1 (preemergentní zkoušky) a tabulce 2 (postemergentní zkoušky).Much herbicidal activity for compounds 1 to 13 is obtained with an application of 11.2 to 0.28 kg of active compound per ha. The results are shown in Table 1 (pre-emergence tests) and Table 2 (post-emergence tests).

Tabulka ITable I

Zkoušky preemergentní účinnostiPreemergence tests

Sloučenina Číslo Compound No. Dávkování kg/ha Dosage kg / ha RK RK BV BV BE BE AB AB ŘE RE HS HS LO LO BA BA KU KU so Sat 1 1 2,24 2.24 - - 90 90 90 90 80 80 0 0 100 100 ALIGN! 100 100 ALIGN! 10 10 0 0 0 0 0,56 0.56 - - 70 70 50 50 40 40 0 0 90 90 100 100 ALIGN! 0 0 0 0 0 0 0,28 0.28 - - 50 50 10 10 0 0 0 0 70 70 10 10 0 0 0 0 0 0 2 2 2,24 2.24 - - 90 90 90 90 90 90 20 20 May 100 100 ALIGN! 100 100 ALIGN! 50 50 10 10 20 20 May 0,56 0.56 - - 90 90 90 90 20 20 May 0 0 100 100 ALIGN! 100 100 ALIGN! 10 10 0 0 0 0 0,28 0.28 - - 60 60 20 20 May 0 0 - - 50 50 80 80 10 10 0 0 0 0 3 3 2,24 2.24 - - 100 100 ALIGN! 100 100 ALIGN! 40 40 10 10 100 100 ALIGN! 100 100 ALIGN! 0 0 0 0 20 20 May 0,56 0.56 - - 100 100 ALIGN! 90 90 0 0 0 0 100 100 ALIGN! 90 90 10 10 0 0 0 0 0,28 0.28 - - 10 10 40 40 60 60 0 0 90 90 90 90 0 0 0 0 0 0 4 4 0,56 0.56 10 10 60 60 - - 30 30 - - 90 90 90 90 - - - - - - 0,28 0.28 10 10 40 40 - - 10 10 - - 10 10 - - - - - - - - 5 5 2,24 2.24 - - 60 60 50 50 10 10 0 0 80 80 90 90 30 30 20 20 May 0 0 0,56 0.56 - - 10 10 0 0 10 10 0 0 10 10 50 50 0 0 0 0 0 0 0,28 0.28 - - - - - - - - - - - - - - - - - - - - 6 6 2,24 2.24 - - 90 90 70 70 0 0 0 0 100 100 ALIGN! 100 100 ALIGN! 10 10 0 0 10 10 0,56 0.56 - - 90 90 90 90 0 0 0 0 90 90 80 80 0 0 0 0 10 10 0,28 0.28 - - 30 30 10 10 0 0 0 0 10 10 0 0 0 0 0 0 0 0 7 7 2,24 2.24 - - 100 100 ALIGN! 90 90 50 50 0 0 90 90 90 90 10 10 10 10 40 40 0,56 0.56 - - 80 80 10 10 0 0 0 0 20 20 May 10 10 0 0 0 0 0 0 0,28 0.28 - - - - - - - - - - - - - - - - - - - - 8 8 2,24 2.24 - - 100 100 ALIGN! 100 100 ALIGN! 10 10 30 30 90 90 90 90 30 30 10 10 0 0 0,56 0.56 - - 20 20 May 20 20 May 20 20 May 10 10 80 80 20 20 May 0 0 0 0 0 0 0,28 0.28 - - - - - - - - - - - - - - - - - - - - 9 9 2,24 2.24 - - 50 50 20 20 May 40 40 - - 20 20 May 90 90 10 10 20 20 May 30 30 0,56 0.56 - - 0 0 0 0 0 0 - - 20 20 May 50 50 10 10 10 10 10 10 0,28 0.28 - - - - - - - - - - - - - - - - - - - - 10 10 2,24 2.24 - - 60 60 60 60 0 0 - - 80 80 20 20 May 0 0 0 0 0 0 0,56 0.56 - - 0 0 0 0 0 0 - - 0 0 0 0 0 0 0 0 0 0 0,28 0.28 - - - - - - - - - - - - - - - - - - - - 1 1 1 1 2,24 2.24 - - 100 100 ALIGN! 90 90 50 50 10 10 100 100 ALIGN! 100 100 ALIGN! 60 60 0 0 0 0 0,56 0.56 - - 90 90 50 50 0 0 0 0 50 50 40 40 0 0 0 0 0 0 0,28 0.28 - - - - - - - - - - - - - - - - - - - - 12 12 2,24 2.24 - - 90 90 90 90 70 70 20 20 May 100 100 ALIGN! 100 100 ALIGN! 10 10 20 20 May 0 0 0,56 0.56 90 90 70 70 1 0 1 0 10 10 100 100 ALIGN! 100 100 ALIGN! 0 0 0 0 0 0 13 13 2,24 2.24 - - 100 100 ALIGN! 90 90 90 90 0 0 100 100 ALIGN! 100 100 ALIGN! 10 10 10 10 0 0 0,56 0.56 - - 90 90 70 70 20 20 May 0 0 100 100 ALIGN! 90 90 10 10 0 0 0 0

Tabulka IITable II

Zkoušky postemergentní účinnostiPost-emergence efficacy tests

Sloučenina číslo Compound number Dávkování kg/ha Dosage kg / ha RK RK B7 B7 BE BE AB AB ře re HS HS LO LO BA BA KU KU so Sat 1 1 2,24 2.24 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 90 90 70 70 90 90 0,56 0.56 - - 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 90 90 60 60 60 60 0,28 0.28 - - 70 70 60 60 90 90 7070 100 100 ALIGN! 60 60 96 96 50 50 80 80 2 2 2,24 2.24 - - 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 90 90 90 90 0,56 0.56 - - 90 90 90 90 90 90 90 90 100 100 ALIGN! 100 100 ALIGN! 90 90 90 90 60 60 0,28 0.28 - - 90 90 90 90 90 90 80 80 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 70 70 80 80 3 3 2,24 2.24 - - 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 66 66 96 96 0,56 0.56 - - 90 90 90 90 100 100 ALIGN! 80 80 100 100 ALIGN! 100 100 ALIGN! 90 90 10 10 80 80 0,28 0.28 - - 90 90 90 90 100 100 ALIGN! 70 70 100 100 ALIGN! 100 100 ALIGN! 90 90 50 50 80 80 4 4 0,56 0.56 20 20 May 100 100 ALIGN! - - - - - - 100 100 ALIGN! 100 100 ALIGN! 90 90 80 80 60 60 0,28 0.28 90 90 90 90 - - 70 70 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 90 90 20 20 May 40 40 5 5 2,24 2.24 - - 90 90 90 90 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 90 90 90 90 60 60 0,56 0.56 - - 90 90 90 90 100 100 ALIGN! 70 70 90 90 100 100 ALIGN! 90 90 60 60 30 30 0,28 0.28 - - 80 80 80 80 100 100 ALIGN! 60 60 80 80 100 100 ALIGN! 80 80 30 30 70 70 6 6 2,24 2.24 - - 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 40 40 80 80 0,56 0.56 - - 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 80 80 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 20 20 May 80 80 0,28 0.28 - - 30 30 20 20 May 100 100 ALIGN! 90 90 90 90 90 90 70 70 60 60 40 40 7 7 2,24 2.24 - - 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 70 70 80 80 0,56 0.56 - - 90 90 90 90 100 100 ALIGN! 70 70 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 70 70 80 80 0,28 0.28 - - 80 80 70 70 90 90 90 90 100 100 ALIGN! 100 100 ALIGN! 70 70 10 10 40 40 8 8 2,24 2.24 - - 70 70 70 70 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 90 90 60 60 60 60 0,56 0.56 - - 60 60 60 60 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 80 80 40 40 40 40 0,28 0.28 - - 90 90 70 70 90 90 90 90 100 100 ALIGN! 100 100 ALIGN! 50 50 20 20 May 50 50 9 9 2,24 2.24 - - 100 100 ALIGN! 90 90 90 90 80 80 100 100 ALIGN! 100 100 ALIGN! 90 90 90 90 50 50 0,56 0.56 - - 90 90 90 . 90. 90 90 30 30 90 90 100 100 ALIGN! 90 90 70 70 60 60 0,28 0.28 - - 20 20 May 30 30 90 90 - - 90 90 90 90 90 90 40 40 10 10 10 10 2,24 2.24 - - 90 90 90 90 80 80 0 0 90 90 90 90 • 90 • 90 80 80 70 70 0,56 0.56 - - 90 90 90 90 90 90 90 90 90 90 90 90 40 40 40 40 0,28 0.28 - - 10 10 10 10 70 70 - - 80 80 70 70 50 50 10 10 50 50 1 1 1 1 2,24 2.24 - - 90 90 90 90 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 90 90 50 50 6060 0,56 0.56 90 90 90 90 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 60 60 10 10 50 50 0,28 0.28 - - 30 30 20 20 May 90 90 80 80 100 100 ALIGN! 100 100 ALIGN! 70 70 10 10 10 10 12 12 2,24 2.24 - - 90 90 90 90 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 60 60 90 90 0,56 0.56 - - 90 90 90 90 90 90 90 90 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 40 40 70 70 13 13 2,24 2.24 - - 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 90 90 90 90 0,56 0.56 - - 90 90 90 90 100 100 ALIGN! 90 90 100 100 ALIGN! 100 100 ALIGN! 100 100 ALIGN! 30 30 70 70

Jako referenční produkt lze pro sloučealny obecného vzorce I uvést sodnou sůl acifluorfenu obecného vzorce ť As a reference product can be for sloučealny formula I include sodium acifluorfen Formula T

Cl COONaCl COONa

která je rovněž známá pod označením Tackle. Obecně vzato Tackle se vždy'používá jako po!^tem^i^j^(^r^1tn:ího herbicidu a jeho preemergentní aktivita je nízká. Při dávlcovváii, ve kterém se Tackle používá (0,25 až 1 kg/ha) má tato látka horěí aktivitu než sloučeniny podle vynálezu (40% potlačení). Má-ϋ se dosáhnout potlačení alespoň 80 %, má se dávkování zvýěit na - 1i 2 až 2 kg/ha.also known as Tackle. In general, Tackle is always used as a herbicide and its pre-emergence activity is low. it has a worse activity than the compounds according to the invention (40% suppression), in order to achieve a suppression of at least 80%, the dosage should be increased to - 2 to 2 kg / ha.

Sloučeniny, které jsou účinnou složkou prostředků podle vynálezu jsou naproti tomu aktivní z více než 80 % na velký počet plevelů při preemergentní aplikaci v běžně používaných dávkách, tj. 0,25 až 0,8 kg/ha. V zemědělské praxi se dává přednost preemergentním prostředím před poetemergentními prostředky, poněvadž preemergennní prostředky - zaručují, že plevelné rostliny vůbec nevzejdou.On the other hand, the compounds which are the active ingredient of the compositions according to the invention are more than 80% active on a large number of weeds in pre-emergence application at commonly used doses, i.e. 0.25 to 0.8 kg / ha. In agricultural practice, preference is given to pre-emergence environments over post-emergence agents, since pre-emergence agents - guarantee that weeds will not occur at all.

Claims (1)

předmět vynálezuobject of the invention Herbicidní prostředek, vyzne^^ící se tím, že jako účinnou složku obsahuje sloučeninu obecného vzorce IA herbicidal composition comprising as active ingredient a compound of formula (I) OO IIII Cl C-O-R (I) kdeCl C-O-R (I) wherein R představuje alkylskupinu s 1 až 4 atomy uhlíku substituovanou kyano-, acettl-, feny-, fenoixfenyl-, fenoxy, akry]^!-, meetaktrloyl-, nitro-, metyH^l^io, mettylsstfonnl-, meetyl8slffryl-, methoxy- nebo ethoxyskurinot.R is C 1 -C 4 alkyl substituted by cyano-, acetyl-, phenyl-, phenoxyphenyl-, phenoxy-, acryloyl-, methoxyl-, nitro-, methyl-, methyl-, methyl-, phenyl-, methoxyl-, methoxyl- or ethoxyskurinot.
CS81652A 1980-02-01 1981-01-29 Herbicide means CS221819B2 (en)

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US4344789A (en) * 1979-05-11 1982-08-17 Ppg Industries, Inc. Acids and esters of 5-(2-optionally substituted-4-trifluoromethyl-6-optionally substituted phenoxy)-2-nitro, -halo, or-cyano alpha substituted phenyl carboxy oximes, and method of controlling weeds with them
US4797505A (en) * 1982-03-17 1989-01-10 Gaf Corporation Process for the preparation of substituted diphenyl ethers
IL67513A (en) * 1982-02-24 1986-02-28 Velsicol Chemical Corp Tetrahydrofuran and tetrahydropyran esters of phenoxybenzoic acid derivatives and herbicidal compositions containing them
US4398938A (en) * 1982-05-20 1983-08-16 Velsicol Chemical Corporation N-Acylated lactams and their herbicidal compositions and method of use
US4404018A (en) * 1982-06-23 1983-09-13 Velsicol Chemical Corporation Furfuryl amides of phenoxyphenoxyalkanoic acids and herbicidal use
DE3224984A1 (en) * 1982-07-03 1984-01-05 Bayer Ag, 5090 Leverkusen SUBSTITUTED DIPHENYL ETHERS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES
DE3337540A1 (en) * 1983-10-15 1985-04-25 Bayer Ag, 5090 Leverkusen PHENOXYPROPIONYLPHOSPHONIC ACID ESTER
HU190222B (en) * 1984-01-17 1986-08-28 Budapesti Vegyimuevek,Hu Fungicide comprising substituted phenoxy-benzaldehyde as active substance
GB8422701D0 (en) * 1984-09-07 1984-10-10 Shell Int Research Ether herbicides
GB8423252D0 (en) * 1984-09-14 1984-10-17 Shell Int Research Ether herbicides
US5024691A (en) * 1985-02-25 1991-06-18 Ici Americas Inc. Substituted phenoxy benzamide herbicides and methods of use
DE3628317A1 (en) * 1986-08-21 1988-02-25 Bayer Ag PHENOXYBENZOESAEUREESTER
KR0183513B1 (en) * 1994-03-22 1999-04-15 오쯔보 히데오 Wafer slice base peeling system
JP4880473B2 (en) 2004-10-08 2012-02-22 壽製薬株式会社 Therapeutic agents for diseases involving phosphonic acid derivatives and high blood phosphate
EP2990403A1 (en) * 2014-08-29 2016-03-02 Novartis Tiergesundheit AG Anthranilamides, sulfonamides and nitro analogues derived therefrom as anthelmintics

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