SE421103B - COMPOSITION FOR CONTROL OF AIRCRAFT AND WIDE-LEAD SOGRES OR NON-UNSECUTED GRASS GROWERS - Google Patents

Description

7315581-4 virtually destroyed.

It is known, for example, that 70% control of flying oats (the four-leaf stage) is achieved by applying SD-30053 separately at a dosage of 1.1 kg / ha. Upon application of 1.1 kq / ha thereof and 0.42 or 0.84 kg / ha 2,4-D (2,4-dichlorophenoxyacetic acid), the control of flying oats decreases to 29 resp. 25%. Similarly, the addition of 0.14 and 0.28 kg / ha of DICAMBA to SD-30053 and 0.28 or 0.56 kg / ha of BROMOXYNIL to SD-30053 results in another resp. 29, 24, 53 and 53% reduced oat control. DICAMBA is 2-methoxy-3,6- -dichlorobenzoic acid, BROMOXYNIL is 3,5-dibromo-4-hydroxybenzonitrile and 2,4-D is 2,4-dichlorophenoxyacetic acid.

It has recently been found that 1,2-dimethyl-3,5-diphenylpyrazolium salts are useful for the selective control of flying oats.

It has now been found that 1,2-dimethyl-3,5-diphenylpyrazolium fly herbicides can be advantageously combined with broadleaf weed and grass herbicides without loss of either the ability of the pyrazolium compound to selectively control the fly oats in the presence of agricultural crops. or the ability of broadleaf weeds or grass herbicides to control their target plants. Useful pyrazolium salts have the formula: Xm m _g 69 I - N -_- N CH3 CH3 wherein X is an anion with a charge of 1-3, m is an integer of 1, 2 or 3. Such compounds describe % in the published Swedish patent application 7215642-5 (400.4S3). Suitable anions include, for example, halides such as chloride, bromide or iodide, acetate, sulfate, hydroxide, hydrogen sulfate, methyl sulfate, benzenesulfonate, C 1 -C 4 alkoxybenzenesulfonate, C 1 -C 3 alkylbenzenesulfonate, preferably toluenesulfonate such as p-toluenesulfonate nitrate, phosphate, carbonate, bicarbonate, C1-C4 alkanesulfonate, chlorate, perchlorate, thiocyanate, Brå) and Iš).

Suitable hormonal phenoxyacetate broadleaf herbicides 7315581-4 have the formula: H Cl 2 "CH" C'R (VII) wherein R 3 is Cl or methyl and R 5 is -OM, wherein M is an alkali metal ion, preferably sodium or potassium, or -OR 6, wherein R 6 is hydrogen, alkyl-C 1 -C 8 (preferably methyl, ethyl, isopropyl, butyl, pentyl, ethylhexyl, octyl or isooctyl), or a mixture of an acid of formula VII with an ester or a salt thereof, or optionally, that compounds I and VII are a combination such as 1,2-dimethyl-3,5-diphenylpyrazolium-2,4-dichlorophenoxyacetate or 1,2-dimethyl-3,5-diphenylpyrazolium-4-chloro-2-methylphenoxyacetate, the content of component I in the composition is such that 0.27-2.2 kg / ha, preferably 0.55-1, 1 kg / ha, calculated on the pyrazolium cation, is applied in the weed control, and the content of component VII is such that during the weed control, 0.1-11.1 kg / ha is applied, preferably 0.27-0.55 kg / ha, calculated on the weight of the phenoxyacetic acid.

The compositions of the invention, useful for controlling flying oats and broadleaf weeds or undesirable grass plants, can thus be characterized as mixtures or combinations of a 1,2-dimethyl-3,5-diphenylpyrazolium flying oat herbicide with a broadleaf, grass or grass herbicide.

The compositions are prepared by mixing the herbicides either as pure compounds or diluted with diluents or carriers, similar to when mixing herbicidal compositions of the usual kind.

Alternatively, the novel compounds, characterized as a salt having the 1,2-dimethyl-3,5-diphenylpyrazolium cation from flying oat herbicides in combination with a phenoxyacetate anion from the broadleaf grass or grass herbicides, can be used as compositions used for controlling flying oats and broadleaf weeds and grasses. They can be obtained by mixing fly oat pyrazolium herbicides with a suitable phenoxyacetate herbicide.

They can be combined with fly oat herbicides either as free acid or in the form of salts thereof. Isolation of the new compounds can optionally be performed by conventional purification techniques, such as evaporation (in the case of an acid-base reaction), ion exchange, fractional crystallization and the like. Control of flying oats and broadleaf weeds and grasses using the compositions of the invention is carried out, whether they consist of new salts or mixtures of herbicides, by applying the material, preferably dissolved or dispersed in a solid or liquid adjuvant (diluent). or carriers), such as water, on the foliage of the plants to be controlled. Water-soluble salts of fly oat pyrazolium herbicides and a wettable powder, a liquid or an emulsifiable concentrate of broadleaf weed or grass herbicides are usually dispersed in water and applied to the foliage of the undesirable plants in such form.

A surfactant, dispersant, tackifier or the like is usually added to the mixture to improve stem penetration.

About 0.1 to 5.0%, preferably 0.5-3.0% of a surfactant is usually added to the solution or dispersion, and such a surfactant may be selected from nonionic, anionic, cationic and non-ionic. ionic / anionic mixtures. Examples of particularly suitable surfactants are alkylaryl polyglycol ethers, alkylphenol ethoxylates, trimethylnonyl polyethylene glycol ether, nonylphenolethylene oxide condensate, alkylphenolethylene oxide condensate, alkylpolyoxyethylene ethers, polyethylene sorbitanomethoxynoxylethonylethylurethanexylethonylethoxymethyluronylate. However, nonionic surfactants are particularly suitable, especially those with a hypophilic / lipophilic balance between 11 and 16.

The pyrazolium salts and the other herbicides can also be individually prepared as wettable powder compositions, emulsifiable concentrates or the like and mixed in a spray tank in the field.

One can, of course, use any commercially available broadleaf and grass herbicide compositions.

Application is performed by conventional apparatus and technology.

The compositions of the invention are useful not only for controlling flying oats and broadleaf weeds or grass weeds, but they can also be used in the presence of numerous crops, such as wheat, oats, rye, flax, peas, sugar beets, rapeseed and sunflower.

The compositions are applied at the dosage which the consumer finds to be effective against the particular, undesirable plants having regard to the particular environment, their stage of growth, the herbicidal agents selected, the type of composition and the like. For effective control of undesirable plants with the non-hormonal herbicidal compositions, the application is normally carried out in sufficient amounts to give about 0.27-2.2 kg / ha, preferably 0.55-11.1. kg / ha, of the pyrazolium cation.

The herbicidal combinations, containing the 1,2-dimethyl--3,5-diphenylpyrazolium salts and chlorophenoxyacetic acid or an ester or salt thereof or the salts of the pyrazolium cation and the halophenoxyacetate anion, are usually dispersed in water and applied in the form of a spray liquid on water. of the undesirable plants. Water-soluble salts of both the pyrazolium and halophenoxy compounds can be dissolved in water and as such applied to the foliage of the undesirable plants. When desired, a surfactant, a dispersant, a tackifier or the like may also be added to the solution, and the addition of a surfactant, such as a linear alkyl polyoxyethylene ether, to the mixture is usually particularly desirable. The pyrazolium salts and the phenoxy compound can also be individually prepared as wettable powder compositions, emulsifiable concentrates, water-miscible concentrates or the like and mixed in the spray tank in the field.

Of course, any commercially available phenoxyacetic acids, esters or salt compositions can be used. Typical ester compositions consist of: (1) 68% by weight of 2-ethylhexyl ester of 2,4-D, 27% kerosene and 5% mixture of oil-soluble sulfates and polyoxyethylene ethers; (2) 40% by weight of butyl 2,4-D, 57% xylene and 3.0% mixture of oil sulfates and polyoxyethylene ethers; (3) 45% by weight of isopropyl-2,4-D, 52% heavy aromatic hydrocarbon and 3.0% of a linear alkyl polyoxyethylene ether.

Typical wettable powder compositions of the pyrazolium salt and the halophenoxyacetic acid, ester or salt contain about 25-75% by weight of the active compound, 20-71.5% by weight of a finely divided carrier such as attapulgite, kaolin, silica or the like, 1.5-3% by weight of a surfactant such as sodium N-methyl-N-oleyltanate ester of sodium isothionate, alkylphenoxypolyoxyethylene ethanol or the like and 2-3% by weight of a dispersant such as a highly purified sodium lignosulfonate, naphthalene sulfonic acid condensate or the like.

For effective control of undesirable plants, these herbicide combinations are normally applied in an amount sufficient to give 0.27-2.2 kg / ha, preferably 0.55-1.1 kg / ha of the pyrazolium cation. 14-1.1 kg / ha, preferably 0.27-0.55 kg / ha of the phenoxyacetic acid equivalent in the form of acid, ester or salt.

While these herbicide combinations are useful for controlling flying oats and broadleaf weeds in the presence of agronomically significant crops, wheat and barley, they can also be used for controlling these undesirable plants in the presence of rye, flax and peas.

The invention is further illustrated by the following examples, the parts and percentages given being by weight unless otherwise indicated.

Example 1. In the tests reported in Table I, flying oats (Avena fatua) are grown in troughs in greenhouses until they reach the four-leaf stage. They are then sprayed with an aqueous solution containing a sufficient amount of test compound to give 0.16-0.66 kg / ha of pyrazolium cation.

For comparison, test compounds were used separately and in combination with 4-chloro-2-methylphenoxyacetic acid (MCPA), added in a sufficient amount to give 0.27 kg / ha of said compound.

All test solutions are prepared so that they will contain about 0.1% by weight of the biodegradable, nonionic, linear, alkyl polyoxyethylene ether surfactant. Untreated plants were used as controls and four weeks after the treatment the foliage of all plants was harvested and weighed.

The data obtained are summarized in Table I, which shows that the addition of 4-chloro-2-methylphenoxyacetic acid to solutions containing a 1,2-dialkyl-3,5-diphenylpyrazolium salt significantly improves the control of flying oats, while the addition of 4-chloro-2 -methyl- phenoxyacetic acid to the commercially available flying oat herbicide 4-chloro-2-butynyl-N- (3-chlorophenyl) -carbamate destroys the control of flying oats. 7315581-4 .www fi nmmwëm fl hwwë fl o> m m fi ow A hwaGwHm> fi> xmmHhm mz \ wx w wc fi hmwoß xx mowvdxäß fifi onmhhm hmw mß \ wx w m flflämmon * rhmnumm: pmånfäa. o om m m _ o .A dä. .Éoüwà vaw fi uinäpssnmnno fi xno O fi ho fi x mm mm * mw.o laßw fl onmhnm fi x fl mm fl olm.m1 fl hPmaHo | m.H um fl ow fi sm fi mß fi ow mr mm * mm.o led fi on mm h mHmh. væ fl ow fl ßm fl wß fi op mm mv * mH.o IEø fl aoumHhmHz fl wm fl o | m.m! HzvwE fl clN.a o ø fl mp »m> .æawwmw ä _ o Éâ flfl IÉQFREÉHS JSÉ: P23» w «m> 23 m. wmwmmww fl ... äwnwwwwwwww fi nmmšmwmwnw »P fl mwp wo <fi š ä» x fi üw H H fi mßma 7315581-4 Exemgel 2.

Flight control in the presence of Waldron wheat In these tests, Waldron wheat was sown in early May. Five days later and several days before the wheat emerges, the flying oats emerge (Avena spp.). When developed to four-leaf stages, selected areas are sprayed with aqueous solutions containing 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate or said compound and 2,4-dichlorophenoxyacetic acid (2,4-D).

The dosages are carried out by applying 0.56 or 1.12 kg / ha of the active pyrazolium cation compound separately and in combination with 0.42 kg / ha of 2,4-dichlorophenoxyacetic acid (2,4-D).

Each solution also contains 0.5% by weight of a surfactant, linear alkyl polyoxyalkyl ether agent. Eight weeks after treatment, the different areas are observed with respect to control of flying oats and wild mustard. The data obtained are compiled in Table II. 7315581-4 uwu al MMN al sm f ævwñ f o> m Show N hwPGwHm> w> & wmnaw m§ \ wx w m flfi hmwo f xx f owvmxsß flfi oumhhm hmm mn \ wz «mn f hwmon x OOO .HGHHOHPQOX mGÜHUQNSQQO in nkïä pmïøw fi mpwa m 93 5 A OÃHÄ LHH fi ëånhmïnww al ßzm.måšwåmïwå * ínnïä Pådæ fi NPWS m OOH vw N <.O + wm. Eïww w fifi wswswm wpw> |: onuHmš wmuwwm> nm fl ||||||||||||||||||||||| | uunnunnuu ||| uu fl | QmmwmwMwMWmmm | mMMmmwHm bö HHommmoN HH H fi wßwe 7315581-4 10 Exemgel å.- Preparation of 1,2-dimethyl-3,5-diphenylnyrazolium ~ 2,4-dichlorophenoxyacetate 1,2-dimethyl diphenylpyrazolium methyl sulfate was transferred to the pyrazolium hydroxide by ion exchange chromatography. This was titrated (aqueous solution) with 2,4-dichlorophenoxyacetic acid. Solid 2,4-D was added and dissolved in a very short time. The pH of the solution was monitored with a pH meter. The addition of the acid was stopped at pH 7 (initial pH was 12-13). This aqueous solution was maintained for 48 hours at room temperature. The pH was about 8. An additional amount of acid was added until pH 7 was reached again. After 24 hours (pH maintained at 7), the aqueous solution was evaporated to a yellow oil and then dried by formation and subsequent evaporation of an azeotrope with repeated use of equal volumes of toluene and dry acetone. Hexane was added together with 5-10% dry acetone. The gel solidified to a white solid, which was filtered off, washed with hexane / acetone mixture and dried. 7.0 g of a lemon yellow solid, m.p. 152-1540, were obtained.

N 2 O 3 C 12 C 25 H 22 Calculated: o 63.97 and 4.72 N 5.96% Found = c 63.67 H 4.69 N 5.90% Example 4.

Preparation of 1,2-dimethyl-3,5-diphenylpyrazolium-4-chloro-2-methylphenoxyacetate 1,2-dimethyl-3,5-diphenylpyrazolium hydroxide in aqueous solution was titrated with 4-chloro-2-methylphenoxyacetic acid (MCPA), a known herbicide, to pH 7 and maintained for 48 hours in this condition. MCPA was added as a solid and dissolved slowly. The aqueous solution was evaporated to low volume (oil) and azeotroped several times with toluene / acetone. Hexane (5% acetone) was added and the oil solidified to a light yellow solid, which was filtered off, washed with hexane and dried. 6.5 g of light yellow solid, m.p. 138-1400, were obtained.

N 2 O 3 Cl 2 C 26 H 25 Calculated: c 69.55 H 5.61 N 6.24% Found: C 68.47 H 5.86 N 6.42% The compound is useful as a herbicide. 7315581-4 ii Examples 5-9 below illustrate the synergistic effect which arises between the two components of the composition according to the invention.

Example 5.

Control of flying oats and broadleaf plants in the presence of winter wheat Test areas were sown with winter wheat (variant McCall).

When the wheat reached the 3-6 leaf stage and the vigorous growth with flying oats reached the 2-3 leaf stage, the areas were treated with an aqueous spray containing 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate or said compound in combination with dimethylamine. the salt of 2,4-dichlorophenoxyacetic acid. The spray is applied under a pressure of 2.81 kp / cm 2 in an amount of 93.54 l / ha. Each of the above treatments was repeated three times and areas measuring 1.83 x 9.14 m were arranged in a completely random block pattern.

After the treatment, there was an initial damage of 5-7% to the wheat, from which the plants recovered. One month after treatment, the percentage control of flying oats and broad-leaved plants achieved was determined. The data thus obtained were transferred to averages and are summarized in Table A below. 7315581-4 l2 ß »É fi šm fi xoqw fi o fi x fl w 1 3.0 å. N> m» Hmwn fl sm fi wume fi w 0.3 ïä ïâ ïä + + 1 vmm flfl maæawñtå fl waoumuwm NH.H | HænwuHu | OA | h0m | H_a | fl> Gmu fl © | m_m | «sumEHw | N. Fi m fl nou lmmmmmn fl n 1 wu> mnm>« m m fl awmmmu wmnmmc fi ncmm E fifl u fi mmn mn \ mM »MÛMHÜM M PM HMUHÜUÜCC. ... HHOHnf f IF HHOÜUGÜUOHQ uawcomñox> fi SSX4 m flfi nmumm 1 1mum> Huvn fl>> m1oHm> HMG al Hmuußmmumo mm al Oman al wnn Soc wu> mßmmHw> M a fl ONU al OX mm mm al wwm> m UMN mnæmx al ABU al xocmuno al xwwlw- bm umu al MMC al ñmaæuwä FLOW WME _ QO f m f naox fi: Oo fi MNA »m f sm flfl uøeuas al onmhåmïnww al ønmwwå f wa al IMA .A3» W FI åpxmwàm 4 H fi wâmß 7315581-4 13 Exemgel 6.

Control of flying oats in the presence of barley Test areas were sown with barley (variant C.M. 76). When most of the grain was in the 3-leaf stage and about 70% of the moderate growth with flying oats was in the 3-leaf stage, the areas were treated with an aqueous spray liquid containing 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate or the aforementioned in combination with the mixed ethanolamine and isopropanolamine salts of 2,4-dichlorophenoxyacetic acid. The spray was applied under a pressure of 1.76 kp / cm 2 and in an amount of 299.3 l / ha. Each of the above treatments was repeated three times and the 6.1 x 30.5 m areas were arranged block by block in a completely random manner.

Three months after the treatment, the percentage control of flying oats (as well as the grain damage: 1-7%) was determined and at the harvest the yield per area was determined. The average of the numerical values thus obtained was determined and is given in Table B below. 7315581-4 l4 w «.« «Mß.« M wm_m «w fl mnE0 \ mx umuænuø. oH fl> Hmc fi¶ mu> msm> aw> m a fl øuucox ø fl> muæmx fl num fl xocwmouo fl x fi ønw m_wæ ß.aß wH> mcm> Hm> m Axmmu fl w m> m Hmuawøwšv a fl ouunwom mm> O. ~> wx fi »um | fi Xo: wmOh0a # fl U |« _N> m Hw flflfl m flfl š fl Ußßñ fiflflfl + um fi ømi fl uwa në flfl aommuæmaæ fl mu | fl w | mm | H> pws fl w1 ~ _H ummaømwwvmm hm mw | æ nmu fl mmc fl ëm wømøc fl an wwä coH »m = Hnaox« sno »Hannu» «« H: w ~> u @ a | aøHHo ~ m »> m fl ænwm fl wlm_m | H> pwe fl w | ~ .A Hmw.» wp fi> fi fi »xwww -4 15 Example 7.

Control of flying oats and broadleaf weeds in the presence of barley Test areas were sown with barley (variant Luther). When the grain was in the 5-6 leaf stage and the heavy presence of flying oats was in the 4-5 leaf stage, the areas were treated with an aqueous spray liquid containing 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate or said compound in combination with the dimethylamine salt of 2,4-dichlorophenoxyacetic acid. The spray liquid is applied under a pressure of 2.81 kp / cm 2 in an amount of 93.54 l / ha. Each of the above treatments was repeated three times and the areas measuring 1.83 x 9.14 m were arranged in blocks in a completely random manner.

After the treatment, there was an initial damage of 6% of the grain from which damage the plants recovered. One month after treatment, the percentage control of flying oats and broadleaf weeds was determined. The median number of the numerical values thus obtained was determined and is given in Table C below. 7315581-4 16 _ muæwx fi uum fl xonwwouø fl x fi w @mo _ | «_ ~> w pwu fi mmn fi am fl wuwa fl w o_wm ~.> M>.> M _>.> M + _ _ + _ _, _ NH.A _ _ umu fläm fi auwûä | . m HMUHÜUÜÉQ HHOHnwGOvn .HHÜUUÄnÜUOHN UÉÜÉOQEOM xwmnn-.me .ÜQMGÜHÜW nuox> m 0Hm> uw text Høunmmmumo mm f wm f n rwwnn twist wu> mnmæHw> m a f onucox o fi> muhmx fl u # others xoGmwou0HM fl @ | wN> m uwu al wwc al šmaæuw fifi w UMS co al UMC al näox fi 300 vum al aw uæmaøm al ä al Melad al Honmuæmah fi mm flfl lm_m | HæuwE fl U | NH> m uxwmwm U Hawßmä 7315581-4 17 Exemgel 8.

Control of flying oats and broadleaf weeds in the presence of barley Test areas were sown with barley (variant Steveland). When the barley was in the 4-leaf stage and the moderate growth of flying oats was in the 3-4-leaf stage, the areas were treated with an aqueous spray liquid containing 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate or said compound in combination with the dimethylamine salt of 2 , 4-dichlorophenoxyacetic acid; or said compound in combination with the isooctyl ester of 2,4-dichlorophenoxyacetic acid. The spray liquid was applied under a pressure of 2.81 kp / cm 2 and in an amount of 93.54 1 / ha. Each of the above treatments was repeated three times and the areas measuring 1.83 x 9.14 m were grouped in blocks in a completely random manner.

One month after treatment, the percentage control of flying oats and broadleaf weeds was determined. The average of the numerical values thus obtained was determined and is given in Table D below. 7315581-4 18 mnæmx fl unm fl xocwwouo fl x w ~ _o | Hu | «_ ~> m cuwumw fl muxoøm fl + + o.mm O.wm O.æm umw fi nmamuwñlšø fl aønmuæm ~ fl.fl | ~>: w« fl w «mm | H> @ | ~. ~ mnhmx fl uum fl xocmwouoax wH_O. | fi U | wN> m Gumummawuxoom fl o.wm m.ßa m.ßm + 1 + N fi.fl umm fi ßmamumñrä flfl aonmuæm | ~> cw «« @ | mm | ~> ~ we fi@|~.~ mummx fl uum fl xocwwouo fl x fl wm. N> m umv fi mmc fl ñmdæuwë fl w h _ + + m_ «m ß ßm ß.ßm umwH§mHæuwE | E9« a0NmH> m ~ HH | H> = w «fi ø | mm | H>» ma fi u | ~. ~ Muæwx fi uo fl xO | vN> m umvamm fifi ëm fi wuwš fifl ~ ~ +. +.

O Nm O wa O_wm _ 1 umu fifl mawuwälës fl aonmuhm ~ H. ~ | H> nw «fl @ | m_m1 ~> uwe fi ø | ~.« Umm fl5 ma> uwE | E fl w fl0 NmHæm m. Fl m Oa O. fi NH.H | fl> mmm | H> #wE fl ø | NH wH> mnm> «w mHaoEG fl> m wwummc fl cnwu m: \ mx ñxßmumm m> m fl mu fl w fl mšv H fi OHun0M H fl wøucwuonm u fl m fl omåox> fl uxM HUm <Hmm m mm <Hmm mm FL> mH> mM of fi u fl etc. No: wmn0ax f u1 «.N> m nnwumw fi huxoom fi nm al aw.> m umu al MMC al ämawvw fi æumëw flfl WS c0 al uw: fi nE0x1H.HmHam uumncm umuaømaåuwE | E = f aOumuæm fi ænwm al wlm_ml fi mume fi VLM. fi> m uxmwmm Q Hawnmß 7315581-4 19 Exemgel 9th

Control of flying oats and broadleaf weeds in the presence of barley Test areas were sown with barley (variant Mora ian). When the barley was in the 4-5 ~ leaf stage and the vigorous growth with fly oats was in the 3-5 leaf stage, the areas were treated with an aqueous spray liquid containing 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate or said compound in combination with the dimethylamine salt of 2,4-dichlorophenoxyacetic acid. The spray liquid was applied under a pressure of 2.81 kp / cm 2 in an amount of 74.83 l / ha. Each of the above treatments was applied to a single area measuring 7.3 x 50.1 m.

Two and a half months after the treatment, the percentage control of flying oats and broadleaf weeds was determined and at the time of harvest the yield was determined. The figures thus obtained are summarized in Table E below. 7315581-4 20 O_Ommm 1 HHOHߧ0M muäwx fl uuw å _o -üöq fl ouo fl x fi øit N ä Pmß fifl m flflfiflfl ä fl wg flfl _ _ _ + + _ m _ »m3 _ ä om om. _ »Mïøm fi wvwa ~ a_H | EnH« 0nmuhm fi Mnww. | fl U | m_m | HæHmEH © lN.a vmwaøm fi æuwë * _33 S o o 3; »As fl owmhšm fi ænww 131m _ .Tïpwa fl øå _ H wH> msm> Hm muw> On uA fl> m fl soom ms \ mx ßÅ \ U ¥ UU% QUD HHOHPQOM HHÜDÜGÜOOHQ PGUCOQÉOM> HP ¥ m mo um m Um 4m> wu> msmmHm> m H fl ouunox Hmm mHæmx al uum al x0cwwoH0Hx fl u | «_ ~> m uwuammc al SM fi æuwä FLOW Owa co al UMO fi nšox H oo uumncm umwanwaæuwâlëd flfl onmnæm fi møwm fi wun_m | H> ume fl u | N_H> m uMwwwm_ W Ham al tra 7315581-4 21 the following experiment was performed using l, 2-dimethyl-3 , 5-Diphenylpyrazolium methyl sulfate, 1,2-dimethyl-3,5-diphenylpyrazolium (ZA-dichlorophenoxy) acetate and 1,2-dimethyl-3. to compare the effect with regard to control after the emergence of flying oats and broadleaf weeds. The herbicidal efficacy of the test compounds after the emergence of the test plants was determined in the following experiments, in which a variety of different monocotyledonous and dicotyledonous plants were treated with the test compounds dispersed in aqueous acetone mixtures. After sowing, the plants were grown in experimental areas for about 2 weeks. The test compounds were dispersed in mixtures of acetone and water in the proportion of 50/50 in sufficient quantity to give about 0.57 kg and 1.2 kg per hectare of the active compound when applied to the plants through a spray nozzle at a pressure of 2. 8 kp / cm2 for a predetermined time period. After spraying, the plants were placed on greenhouse benches and cared for in the usual manner in accordance with conventional greenhouse practice. 3-5 weeks after the treatment, the growing plants were examined and assessed according to the assessment system given below. The data obtained are given in Table F below.

The assessment system used and the plant species used were as follows: Assessment system% difference in growth from the control 0 - no effect 0 l - possible effect l-l0 2 - small effect ll-25 3 - moderate effect 26-40 5 - definitive damage 41- 60 6 - herbicidal effect 61-75 7 - good herbicidal effect 76-90 8 - almost complete killing 91-99 9 - complete killing 100 4 - abnormal growth, ie. a definitive physiological malformation but with a total effect less than 5 on the assessment scale x based on visual assessment of condition, size, force, chlorosis, defective growth and the overall appearance of the plant. 7515581-4 Plant Abbreviations: LA MU PI BA CR WO MG TO NS 22 Atriplex patula mustard pork tenderloin crab grass Green foxtuil flying oats baldersbraa tomato pansy Cyperus rotundus 7315581-4 23 P5 mßww fi m fl wwmmßö N m m m m m m m m m m m m m m m; woèukæoàv HO m m N ø o .w N m m m m BS w »m m m m m m m m m m S; ®o | 0u | ~ = 0-o mmw mmw w I O O O O H O M Q O ßm.O m 2 3: N | »M fl wømwowøw fi å ®cowomu.U / OE mä OM MO dm Å> 09 02 Hß DE då m¶ \ wM H flfl å fl hum U GWE uwuumwwuw nmwnmmmumø mm flfl uaß fl whm fl hwwmm uwuHmUNw>.

PWEOMQQÖ. To demonstrate the technical progress of the invention, comparative experiments were carried out using a 1,2-dialkyl-3,5-diphenylpyrazolium salt, a 1,2-dialkyl-3,5-dialkyl-3-dialkyl-5-dialkyl-3-phenyl-5-dialkyl-3 -pyridylpyrazolium salt and a 1-alkyl-3,5-diphenylpyrazole: The herbicidal activity of the test compounds with respect to control of oats was determined by treating a variety of grasses including flying oats with the test compounds dispersed in a mixture of water and acetone. Germinating plants were allowed to grow in plastic vessels for about 2 weeks and then sprayed with a solution of the test compounds dispersed in a mixture of water and acetone (50 / SO) containing 0.5% by volume of surfactant. A sufficient quantity of the test mixture was applied to obtain an amount of about 4.48 kg / ha of the compound, and such application was carried out using a spray nozzle operating at a pressure of 2.8 kp / cm 2 for a predetermined time. . After spraying, the plants were placed on greenhouse benches and cared for in the usual way. Two weeks after the treatment, the growing plants were examined and assessed according to the above assessment system. The results obtained are given in the table below, from which it can be seen that 1,2-dimethyl-3,5-diphenylpyrazolium methyl sulfate is highly effective in controlling flying oats while 1,2-dimethyl-3-phenyl-5- (4 -pyridyl) -pyrazolium iodide and 1-methyl-3,5-diphenyl-pyrazole are not effective in controlling flying oats.

(The abbreviations used for the plant names are as stated above.) 7315581-4 O H N Q fi m.O O H N O N4.A O O w O wv.w O O O. O ßm _ O O O O O O NH. A O O O O æw _ w c o o S _ o m o o o m .... .H G O O N ww. @ Om É mzäš Éuxn fi m Hwunmmmu uo mm flfifi w mn fi awnmnmm U AHQQMB

Claims (1)

1. 7 31 55 81- '4 I 26 PATENT REQUIREMENTS Composition for the control of flying oats and broad-leaved weeds or undesirable grass plants, characterized in that it consists of a combination of a 1,2- -dimethyl-3, 5-diphenylpyrazolium fly oat herbicide of the general formula -m / \ I fš 1 / \ IX (I) CH3 'CH3 "wherein XIs an anion with a charge of 1-3, m is an integer of 1, 2 or 3, and a broadleaf weed or grass herbicide of the general formula II (VII) wherein R 3 is Cl or methyl and R 5 is QOM, wherein M 1 is an alkali metal ion, preferably sodium or potassium, or -OR 6, wherein R 6 is hydrogen, alkyl-C 1 -C 8 (preferably methyl, ethyl, isopropyl, butyl, pentyl, ethylhexyl, octyl or isooctyl), or a mixture of an acid of formula VII with an ester or a salt thereof, or optionally, that the compounds I and VII are a combination as 1, 2-dimethyl-3,5-diphenylpyrazolium-2,4-dichlorophenoxyacetate or 1,2-dimethyl-3,5-diphenylpyrazolium-4-chloro-2-methylphenoxyacetate, the content of compo The component I of the composition is such that 0.27-2.2 kg / ha, preferably 0.55-11.1 kg / ha, calculated on the pyrazolium cation, is applied during the weed control, and the content of component VII is such that at the weed control applies 0.14-1,1 kg / ha, preferably 0,27-2,55 kg / ha, calculated on the weight of the phenoxyacetic acid. SO PUBLIC AUTHORITY% Sweden patent applications 7408582-0 (A01N 9/02), 7410426-6 (Aom 9/02), 400 453 (Aom 9/22) Japan 13 030/64