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    17 views21 pages

    Jurnal

    Uploaded by

    Sri Dewi
    Obat cacing

    Copyright:

    © All Rights Reserved
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    'US 2008031877441 cu») United States c2) Patent Application Publica Patel et al. (54) SUSPENSION OF ACTIVE COMPOUNDS IN GLYCEROL, (75) Inventors: Smita Patel, Eppstein-Bremtbal (DE); Joachim Baumgartner, Frankiur a. M. (DE) Correspondence Address WOMBLE CARLYLE PLLC APTN: PATENT DOCKETIN P.O. BOX 7037 ATLANTA, GA 30387-0087 (US) SANDRIDGE & RICE, 2ND FLOOR, (73) Assignee: Bayer CropSelenee AG, Monheim i) Appl.No: 12/142,638 ied: h 19, 2008 iON (10) Pub. No.: US 2008/0318774 Al (43) Pub, Dat Dee. 25, 2008 G0) Foreign Application Priority Data Jun. 20,2007 (EP) ov 0120752 Publication Classification Gl) Incl. ADIN 25/32 (2006.01) (52) US.CL 504/103, on ABSTRACT Te preset invention relates to active compound sspensions comprising atleast 60% by weight of glycerol, aprochemi- cally ative compounds, wetting agens,dispersans and ant- foams, and also optionally agents for adjusting eheological properties, acids for adjusting the pl, preservatives aod far {hee componeats, suchas formulation auxiliaries, surfactants and solvents. The aetive compound suspensions and the agro- chemical compositions obtainable therefrom ean be used for ‘controling harm onganisms, US 2008/0318774 AI SUSPENSION OF ACTIVE COMPOUNDS IN GLYCEROL, 10001) The ivention relates to the fil of chemical erop protection, in particular tothe use of particular siepension oncenttates of agrociemicallysetive compounds, ad also Ww grchenial composes comprising ie stapeson [0002] In general, agrochemsically ative compounds foe ‘roppmtection are ao employed in pure form. Depending theares of use and thetype of use, andon physical, chemical ‘and bologieal parameters he ative compound is sed a aetive compound formulation in @ mitre with customary ‘aiares nd adiies. However, the ative compound for mulationof combinations (istres) with father aetvecom- pounds for widening the atvityspecirum andoe for protect Ing he erop plants, forexample by salenes(antidves), san ‘maporant fed of formulation technology since active eo pounds having insome cases quitedillerent physica, hem ‘al ad biological parameters have to be formulated toxether in an adequate manner bere {0003} Formulations of individual active compounds, ike Fommulations of combinations ofa plurality of ative come pounds forcrop protection, should yenerlly be esy to apply 5 easy 10 use and have brad biological ation combined ‘ith high selecivity with respect to the active compounds used, and should aditionally be easy to folate in the Preparation process, Of particular importaace heres i par ticular high chemical and physical stability (toragestailty) ‘of the formulation 10008) Suitable formulations, which allow the demands mentioned above for we in erp proetion to be mat, are ‘encentated suspensions (active compound suspensions) in ‘which the ative compound particles (discantiaous phase) ae suspended in an external iid phase (eontinaovs phase) Depending on the mitre of the enteral phase, the sspen- sions ae classified as suspension concentates (shor names acconling w GCP code, formerly GIFAP code: SC), where the main component ofthe exter phase s water oi ei Uspersions (eee: OD), where the main component of the ‘extemal phase san organic solvent. Thechoice othe espoc- tiveexteral phase i requently determined by testability of the ative compounds in question. In gener, active com- poundswehichareunstabletmwater are formlatedas OD. and Setive compounds Which are unstable in ongane solvent ate formulate os SC. However. in adion hee are also active ‘compounds which cn be formulated ina stable manner ne ther in Water nr in eustomary rzanie solvents. For forme tions of this type of active compounds, in partculer in combination wih ure ative compounds having in each ‘esse ilferent stability inthe extemal phase there are eu rently no convincing saltons 10005} Thisaso includes atempistoreplacetbeeustomary Solvens ofthe extemal phuse By ober guid. Thus, US 200210065198 A] uses, a guid for the extemal phase ly- ol (12-propaneia) in concentrations of 20-80% by weight in combination witha particular nonionie surfactant {0006} According, tis en objet ofthe invention opro- Vide a suitable High fr the extemal phase of active com- pound suspensions, which allows an advantagevos forma tin of agrochemically ative compounds, individually as ‘wells in combination, in particular with view tthe storage Stability of al active compounds Dee. 25, 2008 [0007] Surprisingly, it has now been found that this object is achieved by the active compound suspensions of the present invention, [008] The invention provides an ative eompound suspen- sion, comprising: 10009] "(a at least 60% by weight of glycerol, {10}. () one oF more agrochemically active com- pounds, [0011] (@)oneor more weting agents, [0012] (@) ene ormore dispersant [W013] (e}oneor more antfoams, [oots) and {0013}. (optionally one or more agents for adjusting ‘ological properties, [W016] -(@) ontionaly acids for adjusting the pl 1 fom 251043, 10017] (optionally preservatives (biocides), [W018]. G) optionally further formulation auxiliaries, [W019] G) optionally further suretant, [0020] ck optionally furer solvents [0021] _Hereinbelow, the statement % by weight” (percent ‘by weight) inthe ete description, unless defined otherwise refers tothe relative weight of the component in question, based on the total weight ofthe formulation [0022] "Ina prefered embodiment, these active compound suspensions comprise 10023] (trom 60 0 996 by weight, preferably from 70 to 859% by weinht, of lyeera, [0024] () from 0.1 t0 30% by weight, preferably from $ 10 20% by weit, of aarochemically active compounds, [0028]. (6) from0.1 w 20% by weight, preferably from 1 to 5% by weight, of wetting agents, {0026} "from 0.1 t0 20% by weight, preferably fom 1 to 5% by weiaht, of dispersant, [W027] e) from 0.02 to 2% by weight, preferably fom 0.20 1.5% by weigh, of antifoams, [0028] (from 010 by weight, preferably fom 0.1 v0 4% by weight, of agents for adjusting rheological prop- [0029] "(from 0103%by weight, preferably fom 03 %0 1.S%oby weinht of acids foradhusting the p10 from 2.5 was, [0030] ch) from 0 10 19%by weiaht, preferably fom 0.08 100.4% hy weight, of preservatives (biocides), [0031] |G) from 010 30% by weit, preferably 15% by weigh, of farther formulation auxiliaries, [0032]. G)fromOto 10% by weight of farther surfactants, [1033] (from 0% 30%eby weight, preferably from 0% 20%by weight, particularly preferably from Oto 13% by ‘weight, of futher solvents [0034] ‘particularly. prefered embodiinent are active compound sispeasions aecording to the invention compris ing 10035] _(@) from 65 to 85% by weight of glyeer, [W036]. () from 0.1 t0 2% by weight of sulfonamide herbicide, preferably thienearbszonet-methy!), [0037] -() from 110 10% by weight of herbicide, prefer ably temboirione, [038] _(b) from 0.5 to $% by weight of salener, prefer ably isonadifen-thy, {0039} () om 0.516 8% by Weight of saener,prefer- bly eyprosulfamide, [0040] (6) from 0.1 to 8% by weight of weting agent preferably ®Monatrope 1620 (AL2575), US 2008/0318774 AI [0041] (2) from 03 w 15% by weight of dispersant, preferably iRDispersogen LFH, [0042] (e) from 0.1 to 2% by weight of antifoam, pr ‘erably ®Rhodorsi 481, [0043] (1) from 0.05 to 3% by weight of an agent for adjusting rheological properties, preferably ®Rhodopot 23, [0044] (1 from 0.05 to 3% by weight of an agent for adjusting theological properties, preferably ® Aerosil 200, [0045] (x) from 0 to 2% by weight of acids for adjusting the pH to from 2.5 to 4.5 preferably citric acd, [046] (i) from 010 196 by weight of preservatives (bio- cides), preferably EProxel GXL, 047] () from 2 10 10% by weight of further formula tion auxiliaries, preferably ammonium sulfate ((echnical rade) [0048] (&) from 0 0 13% by weight of funher solvents, preferably water (deionized) 10049] A further particularly preferred embodiment are active compound suspensions aceording t© the invention ‘comprising [0050] (a) from 75 0 90% by weight of glycerol [W051] (b) from 0.5 10 3% by eight of sulfonamide herbicide, preferably thiencarbazone(-methy)), [052] _(b) from 110 10% by weight of herbicide, prefer ably isoxallucole, [053] (6) from 0-5 to 102% by weight of safener, prefer ably eyprosullamide, [0054] (c) from 0.1 w 8% by weight of wetting agent, preferably Atlox 4894, [0055] (@) from 03 to 15% by weight of dispersant, preferably Atos 4913, [0056] (c) trom 0 0 2% by weight of antifoam, prefer ably ®Rhodoesil 481, [0057] (i from O10 796by weight of an agent for adjust- ‘ng rheological properies, preferably Kaolin W, [W058] (g) from 0 10 2%6 by weight of acids for adjusting the pH to from 2.5 to 4.5, preferably citric acd, [0059] (a) frm Oo 196 by weight of preservatives (bio- cides), preferably Proxel GXL, {0060} (hy) from 00 1% by weight of preservatives (bio- cides), preferably RActicide MBS, {W061} (ky from 0 to 13% by weight of further solvents, preferably water (deionized). 10062] For glycerol (1,2.3-propanetrol) as componenta)ia the formulations according to the invention, itis possible to use al forms and sources known tothe person skilled in the ant, for example from Brenntag, Baerlocber, Fauth Chemie ‘and Riedel de Hen 10063] According © the invention, glycerol of any purity ‘and concestration may be used [0063] The amount of glyeero in the formulations aecord- {ng to the invention (component a) may be fom 6010 90% by ‘weight, preferably from 70 to 85% by weight 10065} Suitable agrochemically active compounds (com: ponent b) are all ative eompovinds which, owing to theie nature, ean be formulated in the active compound suspen- sions according to the invention, i. either on their awn oF ia ‘combination as active compotnd particles inthe discontina- ‘ous phase having a mean particle diameter of 1-5 micron (4S0"1-5j) andiorliguid as ombination partners inthe exter nal liquid phase (continuous phase). Dee. 25, 2008 [0066] Prefered as agrochemically active compounds (componeatb) areal active compounds from the group of the herbicides and/or safeners which are biologically active ‘aginst woods inthe wider sense, herviabelaw also refered to asharmful plants, whereas saleners protector invigorate crop plants, andor from the group of the insecticides and fungi- des, whieh ae biologically active against insets, arachnids fand nematodes of fungi and bacteria in the wider sense hereinbelow also refered to as harmful animals and phyto- pathogenic microorganisms (harmful fungi). Hereinbelw, harmful plants, harmful animals and harmful fungi together are alto referred to as harm organisms. [0067] Active compounds from the group of te herbicides, also comprising plant growth regulators, and safeners; rom the group of the insecticides, also comprising acaricides, rematicides, molluscicides, rodenticides, repellents; and from the group of the fungicides, also comprising bacteri- des and viricides, and also plant nutientsmay be mentioned as being preferred Hereinbelow, the term herbicides com- prises both herbicides and plant growth regulators, the term insecticides comprises both insecticides and acaricides, em- atcides, molluscicides,rodenticides and repellents, and the tem fungicides comprises both Fungicides and bactericides and. virieides unless the context indi Examples of individual agrochemicaly a from the groups mentioned above are [0068] Herbicides [0060] Examples of herbicides are, for example, known active compounds which are based ‘on inhibition of, for ‘example, acctolactate synthase, acety-coenzyme A carboxy Jase, PS I, PSI, HPPDO, phytoene desaturase, protoporphy- ‘inogen oxida, glutamine syathetase, cellulose biosyathe- sis, S-enolpyruvylshikimare 3-phosphate synthetase. Such ‘compounds, andalso other usable eompounds, witha mecha- nismofaction thai, in somecases, unknown or different, are described, for example, in Weed Research 26, 441-445 (1986), oF in the handbook “The Pesticide Mantal”, 12th ceition 2000, or 1th edition 2008 or lth ition 2006/2007, ‘or in the corresponding “e-Pesticide Manual”, Version 4 (2006), published in each ease by the British Crop Protection Council, (hereinafier also abbreviated to “PM"), ad the i craure cited therein, Lists of common names ar also wi able inthe Intemet in “The Compendium of Pesticide Com- ‘non Names” Herbicides which ae know fom the literatire ‘whieh can be combined with the compounds ofthe formula () include, for example, the following aetive compounds (note: the compounels, herbicides a$ well as safeners, are :lerredto either by the common name inaceordance withthe International Organization tor Standardization (I80) or by the chemical names, ifappropriate together with a customary code number: acetocilor acibenolar-S-methyl;acituorfen (sodium): aclonifen; AD-67; AKI 7088, ie, [{[1(5-2- hloro-4-(riflaoromethyl)phenoxy]-2-nitrophenyl]-2-meth= oxyethslidenelaminoJoxy}acetic acid and its methyl ester: lachlo,alloxydim( sodium); ametryn; amicarkazone, ami Sochlor, a ammonium sulfamate; aneimidol;aniofos;asulam;atrazin: aviglyeine;aafendin,azimsulfuron (DPX-A8947);aziprot ‘yn; barban; BAS $16 H, ie. S-lluoro-2-phenyl-4H-3,1-ben- ‘oxazin-d-one;_ beflubutamid, benazolinCethyl); bencaeh- ‘one; bonfuralin; bonfuresate; benoxacor, bensulfuron(- methyl; bensulide; —bentazone: —_enzfendizone: bbenzabicyclon, benzofenap; benzolluor, beazoylprop(- ethyl); benzthiazaron; bialaphos; bifenox: bispyribac(-so- US 2008/0318774 AI dium), borax; bromacil; bromobutide; bromofenoxim; bro= moxynil (oetanoate); bromuren; buminafos; busoxinone: butachlor;hutafenoel, utamifos; butenaehlor,buthidazole: butralin;butroxydim, butslate;ealenstole (CH-900); carbe- ‘amide; carfentrzone(ethyl); caloxydim, CDAA, ie. 2-chloro-N,N-i-2-propenylacetamide; CDEC, ic. 2-chloro- allyl dieshyldithioearbamste; chlomethoxyfea: chloramben: chlorwitop-butyl, chlorbromuron; clorbufam: chlorfense: chlorfenprop; chlorfturecol(-methy?);chlorfiurenol(-me= thy); chloridazon; chlorimoron(-ethyl; chlormequat(-chlo- ride); chlormesulon (ICT-A0051); eblonitofen; ehlorotolu- ron; chlowxuron; chlogproptm; ehlorsulfiron; chlorthal- ‘dimethyl; chlonbiamid; chlortolueoa, cinidon(-methyl and athy), cinmethylin; cinosulfuron; ciefoxydim, clthodim: ‘lodinafop and its exter derivatives (eg elodinafop-propar- yl): clofencet; clomazone. clomeprap: eloproxydit clopy= ralid: clopyrasulfuron(-meliy), cloguimtocet(mexsl):clo- ransulam(-methy!), camyluron JC 940); eyanamide; ‘eyanazine; cyeloate; cyelosulfimuron (AC 104): eycloxy dim: eyelunon; cyhalofop and is ester derivatives (eg butyl ‘ester, DEH-112) eyperquat;eyprazine;eyprazole; eyprosul- Jiamide; dsimuron; 24D, 2.4-DB; dslapon; daminozide; yl, halo -Cyalkonycarbonyl halo, C,)alk enyloxycarbony!, balo-(C,-C.)-alkynyloxycarbonyl, {0132} Ris 1, (CCyyall, C,-C, pao. hal (C.-Cy}allgh, haloC,-C,)alkony o halogen (Ch Be Dy {0133} Lis zero or 1, [0134] Ri! is (C.-C, -alkyl, (C,-C,)-alkoxy, (C,-C.)- alkenyloxy, (C,-C:,)alkynyloxy. (C.-C, }alkylsulfonyl (CC. rallylearbonyl, (C.-C, alkoxsearbonyl, (C= C,yalkeayloxyearbonsl. (C.-C) alkynploxyearbony halo-(C,-C.)alkyl, halo-(C,-C,)-alkoxy, halo-(Cy-C)- alkenyloxy,halo“C.-C,alkynylony, alo(C-Cy)= alkylsulfonyl, halo-(C,-C,)alkylearbonyl, halo-(C,- CealkoxyearbonylhaloxC.-C,)akenyonyearbony hlooC.-C,)-alkynyloxycarbonsl, CONRR {0135} R'? is halogen (F, Cl, Br, 1), (Cy-Cehalkyl, (C,- Covalkoxy, (C,-Cq)-alky sulfonyl, (C.-C. alkonjear bony, (Ce,Salhenylonyearbonyl (Cs-Go>alkyny- loxgearbonhal-(C-C, allyl alodCy-Ca) aly, halo(Cy-Cy>allyultny halo -C,-alkonyearbo- as, halo(C,-C,alkenvloxvearbonyl, halon) llyayoxyestbony [0136] Ris (C,-C, alkonycarbonyl,(Cy-C,)-alkeny- loxyeatony. (CC,)alkyaylongearbonsl, (CC) alk (C,-C,)-lkoxy,(C,-C,)alkynlfony, halo C, alkoxycarbonyl haloXC-C,yakenyloxyearbony, hiloC,-Cy)allynylonyeartony! halo(Cy-C,)allyl halos -Cpatkoxy,hlo(C -C alkylsltony,hako= s2n(F, Chi D,CONRR" ot Rr abeteroeyelic ring ‘which may be saturate, Unsaturated or aromatic and which prefenbly contin 4-6 ring sfoms and one or nore heteroatoms fom the group consisting oN, Oand Stand which ay be unsubstitted or substituted by one cormoresubsitvens, preferably fom the group consist ing of (Cy-Cralkyl (Cy-Cypalkony, halowC-Cy)- ally halo4C,-C3)alkoxy and halogen, pariclary rekably At yy < aN 0137] RM is H, halogen (P, C, Be, (C-Cbalby halo{C-C,halky Dee. 25, 2008 [0138] R'is HL (C.-Caalkyl, halo4C,-C, alkyl [0139] RE is (Cy-Copatkyt, (C-Co-akony, (CCQ) alkenyloxy,(C3-C,rallynylony (C)-C, alkysulfony, (Cr-C,)alkylearbonyl, (C-C,)alkoxyearbonyl, (C= C.alkenyloxycarbonyl, (C.-C, )alkynylongearbo halo-C Cally halo(C -Cy)alkory, halo(CCa) alkeaslony,. balo-C,-C,)alkynyloxy,halo(C;-Co) alysulfonyl, halo-(C,-C,)-alkylearboayl, halo-(C Cgralkoxyearbonyl,halo-C,-C,)akenyloxyearbons, hulo-(Ce-Cralkynyloxyearbonyl, CONR'R®, in par: ticular SO,rthyl and [0140] Rand R" independently of one anotber ae H, CCppallyl, halotC,-Coralkyl, (CCopalkenyl (C-Coyhabaitenyl, (C-Coalkyayh, CC) Toatkynyl, or NR'R™ forms a heteroeyeli rg which may be saturated, unsaturated or aromatic and which prcferbly contains 46 ring atoms and one or more heteroatoms from the groupeonsisting oN, OandS and Which may’ be unsubstituted oF substituted by one or tore substituents, preferably from the group consisting of (C-Cypalksl (C,-C,)atkony, haloC,-C, pak, halo-(C,-C,yatkoxy and halogen, (0141) Panicuary prefered heteroarytslfonytureas are {or example, nicosulfuron and is salts, suchas the sodium salt rimsulfron adits salts such a the sodium sal, thifen- sulron-methsl and its salts, sueh a the sodium salt pyre 2osulfuron-thy and its sls, such a the sodium sal, up sulfaronsmethsl and its sits, such as the sodium sit, sulfsulfiron and its salts, such asthe sodium sat, trio ysulfuron and its sits, such asthe sodium sat, zimsalion fd its salts, such as the sodium sal, flazastfuon and its salts, suchasthe sodium salt and flocetosulfuron (1-114, 6-dimethoxy-2-pyrimidiny! amino carbons) fo- syl|-2-pyriinyl|-2-luoropropyl_methoxyacetate) and its salts, soe asthe sodium salt [0142] For the purpose of the presen invention, the sulk onamides (Component b) contsined in the formulations secording to the invention ar in each caseto be understood as ‘meaningalluse forms, such ss acids, esters, salts andisomes, such as stereoisomers and optical isomers. Thus, in addition to neutral compounds, their salts with inorganic andlor ‘organic counterions are in each ease meant to be include Thus, sulfonamides are capable of forming sats, forexample, in which the hydrogen ofthe —SO,—NH group is replaced by an agriculturally suitable cation. These sas are, for example, metal sls, in particular alkali metal salts or alkse Tine earth metal salts in particule sodium and potassium salls or else ammonium salts or salts with organic amines Salt formation may als take place by alton of an acid to basic groups, suchas, for example, amino and alkylamino. Acids suitable for this purpose are strong inorganic and fnuanic acids, for example HCI, HBr, H,S0, oF HNO, Pre- feredestersaretheslkylesters, in paticulartheC alkyl esters, sch as methyl eters [0143] Whenever the term “acyl radical” is used in the abovementioned description, this means the radical of an ‘organic acid which is formally formed by removing an OF arvop fiom the onanie acid, for example the radical of a carboxylic acid and radicals of aids derived therefrom, such a thioearboxylic seid, unsubstituted oF N-substitted im nocarboxylic acids or the radicals of carbonic monoesters, ‘unsubstituted or N-substituted earbaminie acids, sulfon acids, slfini acids, phosphonic acid, phosphine aids. An ‘cyl radical is preferably formyl or ae fom the group con- US 2008/0318774 AI sisting ofCO—RY,CS—R°,CO—OR',CS OR", CS_SR’, SOR’ and SO,R, where R° isin each ease # C,-C,o-hydr- carbon radical, stch as C,-C; alkyl or C-C aryl which is, tunsubstituted or substituted, Tor example by one oF more substituents from the group consisting of halogen, such as P, ‘C1 Br I, alkoxy, halolkoxy, hydroxyl, amino nitro, eyano and alkylthio, or R° is aminocarbonyl or aminosoltony!, where the two lastmentioned radicals are unsubstituted, N-monosubstinuted or N.N-disubstitted, for example by substituents from the group consisting of alkyl and aryl. Acyl js, for example, formyl, haloalkytearbonyl, alkylearbouy], such as (C,-C,)alkylearbonyl, phenylearbonyl, where the phen ring may be substituted, or alkyloxyearboayl, sch as {C.C.}alkyloxyearbonyl, pheayloxyearbonyl, benzyloxy= ‘carbonyl alkylsulfonyl, suchas (C,-C,)alkylsulfonyl alkyl suliny, such as C,-C,-(akysulfinyD) N-alkgt-1-iminoalky, such as'N--(C,-C,)-T-imino-{C,-C,)alkyl, and other radi= cals of organie acids, A hydrocarbon radical is a straight ‘hain, branched or eyelic and saturated or unsanurited al Phatic or aromatic hydrocarbon rica, for example ally, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl. A hydo= ‘carbon radical has preferably 1 t0 40 carbon atoms, with preference | to 30 carbon atons; with particular preference, @ hydrocarbon radical s alkyl, alkenyl or alkynyl having up to TReaebon atoms oreyeloalkyThaving3, 4,5, 60r Fring atoms ‘orphenyl. Arisa mono-,bi-orpolyeyetie aromatic system, Jor example phenyl, naphthyl, tetrahydronaphtyl, indeny!, indanyl, pentalenl,voreayand the lke, preferably pheny! Aleterocyclic radical or ring (heterocyclyl) ean be saturated, Unsaturated or hetersaromatie and unsubstituted or sabst- tuted; it preferably contains one or more heteroatoms in the ring, preferably from the group consisting oN, Oand S:itis preferably an aliphatic heteroeyely radical having 3 0 7 ring ims or @ heteroaromatic radeal having S or 6 ring stoms ‘and contains 1, 2.073 heteoatoms, The heteroeyelie radical ‘can, for example, be a heteroaromatic radial or ving (bet- ‘eroaryl), such as, for example, a mono», bie or polyeyelic fromatic system in which at least one ring contains one oF more heteroatoms, for example pyridyl, pyrimidiny!, pyridazinyl pyrazinyl, riazinyl,thienvl, thiazoly, oxazoly, Jul, pyzrolyl pyrazoly and imidazoly, ort isa partially oF fully hydrogenated radical, sue as oxiramy oxetanyl, pyr rolidyl, piperidyl, piperazinyl, triazolyl, dioxolanyl, mor- Pholiny tetmaydrofuryl. Preference is given to pyrimidiny] ‘and teazinyl Shitable substituents fora substituted heteno= ‘clic radical are the substituents mentioned further below, and adltonally aso oxo. Theexo group may also be present the hetero ring atoms, which may exist indifferent oxida= tion states, for example in the ease of N and S. Substituted radicals, Such as substiuied hydrocarbon radicals, for ‘example substitited aly, alkenyl, alkynyl, aryl, phenyl and benzyl. or substituted heterocyclyl oF heteroaryl, ae, for ‘example, a substituted radical which is derived from an ‘unsubstituted parent compound, where the substituents are Jor example, one or more, preferably 1,2 oF 3, radicals from the proup consisting of halogen, alkoxy, haloalkoxy, aky- Ithio, hydroxyl, amino nitro, carboxyl, cyano, ido, alkoxy ‘carbonyl, alkylcarbonyl, formyl, earbamosl, mono and «lalkylaminocarbony!, substituted amino, such as acylamino, ‘mono and dialkylamino, and alkylsulfiny, haloalky!-sulti nyl-alkylsulfonyl,haloakysulfonyl and, in the case of eyelic radicals, also alky! and haloalkyl, and unsaturated aliphatic radials which comrespond tothe saturated hydrocarbon-con- taining radicals meationed, such as alkenyl, alkynyl alkeny= Dee. 25, 2008 Joxy,alkynyloxy, ete. Among the radicals with carbon at preference is piven to those having 1 to 4 eaebon atoms, ia panicular | oF 2 carton atoms. Preference is generally given {o substituents from the group consisting of halogen, for example fluorine and elorine. (C,-C,)lkyl preferably ‘meth oe thy (C,-C,)halealt, preferably ivorom- ets, (C\-C,yalkoxy, preferably methoxy or ethoxy, Cy- Cyhaloalkony, nitro and eyano. Paricular preference is ain hore to the substitvens methyl, methoxy and chlorine Unsubsitated or substuted phenyl is prelerably phenyl ‘which is unsubstiuted or mono- or poystbstitued, pele bly substituted up to thre times, by idatial oe diferet radicals, preferably trom the group consisting of halogen, (CL,hallsl C,-C,alhors, (C-Cy)-aleallsl, (C.-C, baootoy and nitro, Forexampleo- m-and poy, dimeth- Yipheay, 2, 3-an4-hlorophony, 2-3 and rire unl -rchiorophony, 23.5 2,5-and 23 -chlorophen, me and pmethoxyphenyl Cyelalky isa earboeyelic ‘strated rng system having preferably 3scatbon atoms, for example eylopropy, eyelobuty, eylopeny or eyelohens ‘Tae carbon skeleton o the earhon containing mda, seh asalkyl alloy, haley, baloalkox:alkylamino and alky- io and the corresponding unsatrstd andor substituted radicals, can in each case be straight-chain or branched. In these radicals, preference is given othe lower carbon ske- cons having forexample, lt Gearbonatonsand nthecase oF unsaturated groups, 206 earbon atoms, unless specified oxhervse AIK) radical, also in the composite meanings such a alkoxy, Ishak, et, ar, for example, meth, cil 2-0 isopropyl no, o 2-butyl peat, hexyl Such as ashen, Sbohexyl and 13-dimethybuty, hep suchas-heps, method 14-dieblpenty halk yl and alkynyl radicals have the meaning ofthe possible ‘saturated radicals which comespond ta he ally radical: atkenylis, fr example allyl -nethylprop2-en--y2-me- thylprop-2-en--yh, bu-2-en--yh bul-SeneL-yl, rmethy bcden-l-yl and) metiylbut2-en-1-yt alkynyl is, for example, propagyl, but-2yn-I-y,but3-yn-Lyl, methyl but3:yn. Ie, Halogen is for example, Horne, chlorine, bromine or iodine Halal, lens] and alkynyl is alk alkenyl and alkyl respoctively, which is partially or fully Substitute by halogen preferably by Murine, chlorine and! ‘orbromine, in percular by fluorine or chlorine, for example CFs, CH, CULE, CF,CEs, CULFCUCL, CC, CHCl, CH.CH,CK haloathony is, Tor example, OCF. OCHE, OCHE-CF,CF,0, OCH,CP, and OCH,CH,Ck this applies conespondinaly to hella and otberhalogen substitu radical [0144] From among the ative compounds fom the pup othe sulfonamides and their salts (Component a) very pare ticular preference is given to proposyearbazone and is sodium’ salt (propoxyearbazone-methy-sodium), methyl 414 Sihydeo"smetbony-4-metiylS-oxolIT- 3.4.ia- ‘ol-yearboxamidosulony|}-S-methylthiophene--car- toxytate and its sodiim sal, asidoslfuro and its sodium salt amidosolfuron-methy-sodium), iodosulfuon-methy aust sodium st Godosulforon-methysodium), foram {iron and its sodium salt thifensulhien-methy! and is sexi salt ad mesosulfurossmethyl and its soi salt. {0145} Ia gener, the formulations secording tothe iaven- tion comprise the ative compounds fom the grokp ofthe sulfonamides and their salts (component b) in amounts of US 2008/0318774 AI (0.1-800% by weight, preferably 1-75% by weight, particularly preferably 3.500% by weight, very particularly preferably 5.25% by weight [0146] ‘The agrochemically active eomponndls may also be growth regulators. Examples ofthese are eyclanilide,ethep= hon tibutos and thidiiron, [0147] Inthesense ofthe present invention, the active cr Pounds comprised! as component b) in the formulations ‘acconting (othe invention are in each case to Be understood as including, in addltion to the neural compounds, also thei salts with inorganic and/or organie counterions. Ths, sul fo- nylareas are capable of forming sats for example, in which the hydrogen of the —SO,—NH group is replaced by an agriculturally suitable eation. These salts are, for example metal salts, in particular alkali metal salts or alkaline earth ‘metal salts, in particular sodium salts and potassium salts ‘else ammonium salts o salts with onganie amines, Salt for ‘ation may’ also take place by adlton of an acid to basic groups, such as, for example, amino and alkylamino. Ackls Suitable for this purpose are strong inorganic and organic acids, for example HCI, HBr, H,S0, or INO, Anexampleis Jodosulfuon-methyl-sadinm. [0148] |The herbicides listed above (compounds from the ‘group of the sulfonamides, plant growth regulators) are Known, for example, from “The Pesticide Manual, 120 edi- tion (2000), 13th edition (2003) and L4th edition 2006), The British Crop Proteetion Councilor from the literature refer ‘ences given aller the individual active compounds [0149] Preference is piven to herbicides, such as represen- tatives from the group ofthe “sulfonamides” defined above, preferably, for example, herbicides with folie activity, such 88 ALS inhibitors (for example sulfonamides, sch as thien- ‘carbazone(-miethyD, Miearbazone, propoxyearbazane oF amicarbazone, or sulfonylureas, such 3s mesosulfuron, Jodosulluron-inethy(-sodium),ethoxysulfuron,amidosul fie ron, foramsulfuron),difufenican herbicides from the class ‘of the benzoyleyclohexane-diones, suc as tembotrione, bro rmoxynil-containing or ioxynil-containing products, herb ies from the class of the aryloxyphenoxypropionates, such fs fenoxeprop-P-ethy, herbicides from the class af the oxy ‘acetamides (or example flufenacet and mefenaeet), herbi ‘ides from the class ofthe triazolopyrimidinesulfonamige derivatives (for example fumetsulam, metosulam), sugae beet herbicides, such a desmedipham, phenmedipham,tho- Jumesate or metamitton, etive compounds from the clas of the HPPD inhibitors (for example isoxailatole,suleotione, mesotrione) or else active compounds from the group of the Phosphomis-contsining herbicides or their derivatives, sich as salts, such as, for example, glufosinate and its ammonium, salt in rcemie form, ie. 2-amino-4-[hydroxy(melhy!pos- phinoyl[-butanoie acid or its ammonium salt the L-enant- ‘omer of glufosinate and its ammonium salt, bikanaos/bial phos, i.e. L-2-amino-4[hydroxy(methy!)phosphinoyl]- butanoy/-{-alaniny-L-slanine and its sodium salt and also lyphosate [0150] Safeners [0181] The agrochemically active compounds may also be safeners. Examples ofthese are [0152] 2) compounds ofthe dichlorophenylpyrazoline- 3-carboxylic acid type, preferably compounds such as thy! -(2/4ichloropheny!)-5-(ethoxycarbony))-5- -pyrazoline3-carboxylate(S1-1) (‘mefenpyr v1", PMD, and related compounds, as describe in WO 9107874: Dee. 25, 2008 [0183] _b) derivatives oF dichlorophenypyrazale cate boxsic acd, preferably compounds suchas etl 1-2 4dichloropheny!)Smeibylpyrazole3-carboxyate (S12), ell 1-2.tdichloropheny).5-soprops}pyre- ole Searboxylato S1-3) ethyl I-2,4cichlonopheny}) E.tedimetletypyrazle-3-curboxslate (Slo) city! 1-Q,4-ichiorophenyD>S-phenylpyraote Sear boxe (1-8) and related compounds described in IEP-A-333 151 and EP-A-260 806; {0184 ")compounts ofthe tiazolecarboxyic avi type, ‘prolenbly compounds such as Lenchlorazole(etiy fe) ie, ethyl 1-(2,4dichlorophenyS.trchlorom- iyi I1)-12,4cazole-carbonylte(SI-8) and related compounds (FP-A-174 $62 and EP-A-346 620); [0185] a) compounds of the S-benzsl- or S-phenvl soxazoline- carboxylic acid ype or the 5.Sipheny- Pisoxazoline Hearbonylie sc type, preferably com pounds sich as ethyl 5-(2,tdichlorabenzyy Hoxaztine carboxylate (S1-7) or ethyl S-pheny- ikoxarolineSceorbonlate(SI-8) — and related ‘compounds as desenibed in WO 91408202, or ety 5, Aiphenyl-2-ioxavalincearboxlate (S1-9) soxaifen- ety) orthe-nepeopy ester (81-10) or ety 5-4-o- rophesy)-Sphenyl--soxaroline-Searboxvlate (SI I).asdeserbedin patent application WO-A.95S107897, [0186] &) compounds ofthe S-quinoineoxvacetc acid type (82), prefemblyIomethylhex-Ioyl (Sechlor§- Uinolinxcetate™ (common name “cloguintocet- fool (82) Gee PM). Lime lbut ll {Gcchlor-4-quinolineoxy acetate (82-2), allyloxybi- 191 Gxcloro--quiolincoxy acetate ($23), Lallylone yprop:231 Gehlon-S-quinlinoxy)veeute (S24), iy (Schlor-S-quinoiseoxy) acetate (82-8), mei {Sechboro Squinlineoryecstte (S26), allyl (S.chlor-S-quinoineoxy)acetate (S2-7), 2-C2-propy~ Tidenciminoxy}-1-thyl” S-hloro-quiolineoxy)e- ciate ($28) 2oxoprop-13] Schloro-S-qunolncexy) Sette (82-9) [0157] end elated compounds, a described in EP-A- 86-750, EP.A.DE 349 and EPLA-IOI 736 uF EP-A-0 492366; [0188] compounds ofthe (Schloo-8-qunolineoxy) ‘alone acid ype, preferably compounls such as diethyl G-chloo-8-qunolineoxy)maonate, dally (Scchloro-S-quinolineoxy)malonate, methyl ell (Scehloro--quinolineoxy malonate and elated con pounds, as described in EP-A-0 58 198; {0159} g) active compounds of the phinoxyacetic or “propionic acid derivative ype or the aromatic carboxy Tic acd type, for example 2,4ichlorophenenyacctic sidleses G4-D), -chloe-2nethyipbenoxypeop ni esters (ssopep), MCPA or Gdihloro-2-meth- ‘oxyhonzoicacilesters(dicamba) {0160} b) setve compounds of the pyrimidine type ‘which are sed a sil-acting safener in rc, for xan 10161] “fenctorin” (PND -4,6-chlor-2-phenyipy- imine) which is known as seer fr prtlchor {0162} i) sive compounds of the dichlooacetamide type. which are frequently wed as pre-emergentsfene cer Goiactng saleners), for example 10163] “dichlormia™ (PM) (-NN-inly 12.2 roacetamie). US 2008/0318774 AI 0164] “R-29148" (-3-dichloroacetyl-2.2 5-1 cllyL-1, oxazoline frm Staller, [0165] “benoxacor” (PM) (~4-dichloroacety-3 4 ydro3-methyl-2H-1 4-benzoxazine) [0166] “PPG-1292" —(-Naally1-N((13-I,13-eimethy-1H-inden yb-3-pyridinecarboxanside, 3.15(tchlorpheny).2.3- imetiylisoxamlicin-slfpyridine,csel-(-cho- rophes)-24 It 2ri7ol-L-sljeyelaheptanal, 2 Aihyaro-S-mthory-2-methyl-[([13- (trifworometypheny ethylene aminoloxg] ines pbeni] SU-12,3-razl-Sone (185336-79-2), methyl 142.Saihydro-2.2imetby Hinde HeimidazoleSearboxylate, 3.4 Srichlon-2.6p%- sidiodicarboniile, mes! 2-Tfeylopropylf-meth- “xypeny imino mth thistle (maton mothylensenzeneaetae, 4-chloo-c-propy oxy {2+ smethony-4(2gropymoxy phen) beazencneetamide, OS) NHB chloropheny!)-2-propyaylloxy|-S-mcthoxyphen)), eily]]--methy!-2-(methytsufony amino] US 2008/0318774 AI tana, 5 4{luorphenl}1 24Juiazolel spine Schloro-6-(24 6aillorophengl)-N{(R)-12.2-in- tylpropyli2.tazolol 1 S-apyrimidine 7-amin, Shloeo-N-(UR)-]2adimethyipropy]] 4,4 ti Iuoropheny) [12 4iiazolo[S-lpyeimidine 7am, N-{14S-beomo-¥chloropyridin-2-yDethy]-2.4diclo~ rnicainame, N-(S-bromo-3-chloropridia-2-y)me- thyl-2.4-dichlornicoinamide, 2-butoxy-Grindo:3-po- prlbeavopyran-tone, N{(Z)|(eyelopropyietiexy) imino} {6iooromethoxs)-23-ieorphes methyl} 2-beusenesectumide, N-G-eliyl3SS- ormylamino-2- lL 43(1-fuor2- _henylethy)-oxyJphenylethyfidenejaminoloxy} ‘methyl -ce(methoyimino)N-meths tenzeneacetamide, N-(2-|Schlor-5-(efloromethy) pyrdin2-slJetil}-24Ciluoromethybenzeneamie, NG ichloro$-tuorabipheny-2y0-3- iidazale-Lebothioc sci 242-([6-3-chlon-2- smetiy phenoxy )-5-uoropyrimiin-4-yoxy) phen) 2{methoxyimino)-N-metbylacetamie 10222] The agoebemical ative compounds can also be Bacteicdes, for example bronopo, dichloophennitapstn, nickel dimethyltiocarbamate, Ksugamyein, cethlione, Francarboxyie aid oxytetracycline,probenarae,streto- nye, toollalam, copper ulate and wer copper camper sitions. 10223] The fungicides (hacericdes) fisted above are, foe ‘example, known from “The Pesticide Mama”, 12th edition (2000), 13 eon (2008) and 4h eition (2006), The Brish Crop Proeetion Counel or the literature references listed alter the indivi active compounds. 0224} Preference is given o Fungicides such as itera bromnconsza, carbendavim, carproami, eyproconazae, ‘edifeaphos,fenanidone, fens, fentins,Hguincnse zoe, josey] aluminum, prodone iprvaicar peneyeuron, prochloaz, propamocar® HCl, prepineb..pyrimetani, ‘piroxamine, tahconazole, tolyuanidechlomaani, te ‘aimeton, adimenel, itloxystbin. 10225] Insecticides 10226) The agrochemical active compounds may also be insooiidosacarcides andr nematic, for example {0227} acetylehoineterse (ACHE) ihibitors carbam- ates, for example alanyearh, aldcar, aldoxyca, allyxyearb,aminoear, Dendocat.benfuracab, buen: car, bulacarh, utocarboxim, butoxycarboxim, car bar carbofuran, carbosulfan, clocthocar, dimes, cthjofencar,fensbucar, feasticcar, formetanate, Furathioear, isoprocar, mietamsodium, methiocar, smetom, metokar, oxansl pirimicar, promecar, ropoxut,thiodicar, thofanox, trimethacar, XMC. sylvearb,tezamate omzanophiosphates, for example acephate, azamathiphos, azinphosmethyl th), tyomo-phosethyl, bromfenvintos (-nety!), batho: fos, casas, carbophenothio,chloethoxyos, chlo- sfeavinphos,clormephos, chlorpyrifos methyl Siiyl)," coumupbos, cyanofephos, cyanophios, hlorfewiaphns,demeton-S-metbyl, demeton-S-et W Dee. 25, 2008 ‘lsufone,dilifs, diazinon, dichlofenthion, dichlorvos! DDVP. dicrotophos, dimethoate, dimethylvinphos dioxabeazofos, disulfoton, EPN, ethion, ethoprophos, cetrimfos, Tamphur,fesamiphos, fenitmthion, fensul- fothion, fenhion, fupyrazofos, fonofos, fomnothion, fosmethilan, fosthazate, heptenophos, iodofenphes, iprobenfos, isazofos, isofenphos, isopropyl O-saliey~ late, isoxathion, malathion, mecarbam, mithacrifo, methamidophos, methidathion, mevinphos, monoeroto- phos, nile, omethoste, oxydemeton-methyl, parathion (Cmethyi-ethyl, pheathoste, phorate, phosalone, phos- ‘met, phosphamiden, phosphocar®, phosim, pirimiphos (Cmethyiethy),profenofos, propaphos, propetamphos, prothiolos, proihoate, —pyraclolos, pyridaphention, Dyridathion, quinalphos, sebufos, sulfotep, suiprofos, {ebupirimfos, temephos, terbulos, tetrchlorvinphes, ‘thiometon, triazophos, rchlorfon, vamidothion 10228] sodium channel modulatorsvoltage-dependent sox channel blockers pyrethroid, forexample acri= nathrin,allethrin (d-is-trans, d-rans), betacyfthrin, Difeathrin, bicalledirin, bioallethein-S-eyclopentenyi isomer, bioethanomethrin, biopermethrin, biores- ‘methrin, chlovaportrin, eiseypermethrin, cis-res- methrin, eis-permethrin, cloeythrin,cyeloprothrin, cyflutrin, eyhalothrin, cypermethrin (alpha-, beta thts, zta-), eyphenothrin, deltamethrin, empenthrin (LR-isomer,esfenvalerate,etofenprox, feuthrin, fen Propathrin, feapyrithria, fenvalerate, Nubrocythrinate, Aucythrinae, fufenprox, umedivin, fluvalinate, fubfenprox, gamma-cyhalothea, imiprothrin, kad thsia, ambd-eyhalothra, metoluthrin, permethrin (cis trans-, phenothrin (1R-trans-isomer),prallethrin, ‘profiuthrin,protifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tauefhavalinate, teithrin, teral- Fethrin, tetramethrin (IR-isomen) trlometrin, trans ‘uthrin, ZX1 8901, pyrethrins(pyrethrum) DDT oxadi- azines, for example indoxacarb semicarbazones, for ‘example metallumizone (BAS3201) 10220] acetylcholine receptor agonists‘antagonistschlo- ronivotinyls, for example acetamiprid, clothianidin,

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