ZA200101786B - Soil granulates with controlled active ingredient release (cr coil granulates). - Google Patents

Description

y 0050/49248 AMENDED SHEET »

Soil-applied granules with controlled release of active . ingredient (s) (soil-applied CR granules)

The present invention relates to soil-applied CR granules which can be obtained by applying an active-ingredient-comprising coating to 'a solid carrier in a fluidized bed with a defined heat input adjustable to 6000 to 25,000 KJ/Kg of coating polymer, to soil-applied CR granules with an active-ingredient- comprising coating of 0.1-25% by weight of one or more active ingredients, 1-40% by weight of one or more coating polymers and 0-60% by weight of one or more additives, to a process for the preparation of these soil-applied granules, and to a method for controlling phytopathogenic fungi, undesired vegetation, undesired attack by insects and/or for regulating the growth of plants using the soil-applied CR granules according to the invention.

It is generally known to use coating polymers for fixing crop protection active ingredients on a solid carrier in such a manner that the active ingredient is only gradually released and can thus develop its action over a prolonged period ("slow-release formulation”). WO-A 92 17424 describes fertilizer granules which are coated with an ionically and covalently crosslinked copolymer of ethylene and the zinc salt of methacrylic acid. EPA 0 380 836 discloses the non-covalently crosslinked, partially neutralized equivalents to the copolymers described in WO-A-9217424 as suitable for coating agrochemicals which are to be released slowly and in a controlled fashion. A process for coating small particles which comprise an active ingredient, which may be a crop protection agent, is described in US-A 4,756,844. However, the disadvantage of the current products is that they still tend to agglomerate greatly, which means that the flowability of the formulated product is lost and that the release rate of the active ingredient cannot be adjusted by means of process control.

A need exists to find a formulation for crop protection active ingredients which does not exhibit these disadvantageous characteristics. 40

A need exists to develop slow-release formulations which allow the use of phytotoxic active ingredients for treating plant diseases. 45 A further need exists to develop novel coating techniques using specific and novel coating polymers which provide the encapsulated active ingredient in a tailored

. 0050/49248 » AMENDED SHEET manner, with a controlled release rate, systemically and transapically over a substantial vegetation period of the plant } in the form of granules for co-drilling. 5s The present invention provides soil-applied CR granules as claimed in claim 1, which is to be considered as an integral part of this specific description.

The present invention furthermore provides a process for their preparation and the use of those compositions which comprise fungicidal crop protection active ingredient for controlling harmful fungi.

The construction of semipermeable monolayer or polylayer coatings on the soil-applied CR granules and exact metering of the heat input supplied into a fluidized-bed apparatus allows the active ingredient to be available for up to a period of over 9 months.

Preferred soil-applied CR granules according to the invention are intended to offer complete protection against fungal pathogens, to be nonphytotoxic and, finally, to replace fungicide spray treatments when they are applied by co-drilling together with the seed of the annual or perennial plant.

Suitable crop protection active ingredients are herbicidal, growth-regulatory, insecticidal and, in particular, fungicidal active ingredients.

Suitable systemic active ingredients which are available belong to the fungicidal substance classes of the azoles, morpholines, valinamides, strobilurins and salicylates as distant derivatives of active ingredients of the Bion® type. Surprisingly, selected experiments in which application was effected in the form of the soil-applied CR granules according to the invention led to similarly successful biological results as when two spray treatments with commercially available fungicides were carried out; in some cases, the biological results were even better.

Thus, surprisingly, when using acetylsalicylic acid as active ingredient component, activity-enhancing effects were observed upon soil application and combination with strobilt ins. 40

The following list of herbicides identifies examples of active ingredients which are possible:

0050/45248 AMENDED SHEET i 3 ) . bl 1,3,4-Thiadiazoles: buthidazole, cyprazole b2 Amides: allidochlor (CDAA), benzoylprop-ethyl, bromobutide, chlorthiamid, dimepiperate, dimethenamid, s-dimethenamid, diphenamid, etobenzanid (benzchlomet), flamprop-methyl, fluthiamide, fosamin, isoxaben, monalide, naptalame, pronamid (propyzamid), propanil b3 Aminophosphoric acids: bilanafos, (bialaphos), buminafos, glufosinate-ammonium, glyphosate, sulfosate b4 Aminotriazoles: amitrol ) b5 Anilides: anilofos, mefenacet b6 Aryloxyalkanoic acids: 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-p, dichlorprop-p (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr,

MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr b7 Benzoic acids: chloramben, dicamba b8 Benzothiadiazinones: bentazone b9 Bleachers: clomazone (dimethazone), diflufenican, fluorochloridone, flupoxam, fluridone, pyrazolate, sulcotrione (chlormesulone), isoxaflutole, isoxachlortole, mesotrione bl0 Carbamates: asulam, barban, butylate, carbetamid, chlorbufam, 40 chlorpropham, cycloate, desmedipham, di-allate, EPTC, esprocarb, molinate, orbencarb, pebulate, phenisopham, } phenmedipham, propham, prosulfocarb, pyributicarb, sulf-allate (CDEC), terbucarb, thiobencarb (benthiocarb), tiocarbazil, tri-allate, vernolate 45 bll Quinoline acids:

] 0050/49248 . AMENDED SHEET @ s : quinclorac, quinmerac ] bl2 cChloracetanilides: acetochlor, alachlor, butachlor, butenachlor, diethatyl - ethyl, dimethachlor, metazachlor, metolachlor, pretilachlor, propachlor, prynachlor, terbuchlor, thenylchlor, xylachlor, s-metolachlor bl3 Cyclohexenones:

alloxydim, tepraloxydim, clethodim, cloproxydim, cycloxydim, sethoxydim, tralkoxydim, 2-{1-[2-(4~-chlorophenoxy) pPropyloxyimino)butyl}—3-hydroxy-5- (2H-tetrahydrothiopyran-3-yl)-2 -cyclohexen-l-one, butroxydim, clefoxydim bl4 Dichloropropionic acids: dalapon bl5 Dihydrobenzofurans: ethofumesate bl6 Dihydrofuran-3-ones: flurtamone bl7 Dinitroanilines: benefin, butralin, dinitramin, ethalfluralin, fluchloralin, isopropalin, nitralin, oryzalin, pendimethalin, prodiamine, profluralin, trifluralin bl8 Dinitrophenols: bromofenoxim, dinoseb, dinoseb-acetate, dinoterb, DNOC bl9 Diphenyl ethers: acifluorfen-sodium, aclonifen, bifenox, chlornitrofen (CRP), difenoxuron, ethoxyfen, fluorodifen, fluoroglycofen-ethyl, fomesafen, furyloxyfen, lactofen, nitrofen, nitrofluorfen, oxyfluorfen ’ b20 Dipyridylenes: 40 cyperquat, difenzogquat-methylsulfate, diqguat, paraquat b21 Ureas: benzthiazuron, buturon, chlorbromuron, chloroxuron, 45 chlortoluron, cumyluron, dibenzyluron, cycluron, dimefuron, diuron, dymron, ethidimuron, fenuron, fluormeturon, isoproturon, isouron, karbutilat, linuron,

0050/49248 AMENDED SHEET

) methabenzthiazuron, metobenzuron, metoxuron, monolinuron, monuron, neburon, siduron, tebuthiuron, trimeturon b22 Imidazoles: isocarbamid b23 Imidazolinones: imazamethapyr, imazapyr, imazaquin, imazethabenz-methyl (imazame), imazethapyr, imazapic b24 oOxadiazoles: methazole, oxadiargyl, oxadiazon b25 Oxiranes: tridiphane b26 Phenols: bromoxynil, ioxynil b27 Phenoxyphenoxypropionic esters: clodinafop, cloquintocet, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, fenthiapropethyl, } fluazifop-butyl, fluazifop-p-butyl, haloxyfop-ethoxyethyl, haloxyfop-methyl, haloxyfop-p-methyl, isoxapyrifop, :

propaquizafop, quizalofop-ethyl, quizalofop-p-ethyl, quizalofop-tefuryl b28 Phenylacetic acids: chlorfenac (fenac)

b29 Phenylpropionic acids: chlorophenprop-methyl b30 Protoporphyrinogen IX oxydase inhibitors:

benzofenap, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, flumipropyn, flupropacil, fluthiacet-methyl, pyrazoxyfen, sulfentrazone, thidiazimin, carfentrazone b31 Pyrazoles

40 nipyraclofen, pyraflufen-ethyl b32 Pyridazines: chloridazon, maleic hydrazide, norflurazon, pyridate

45 b33 Pyridinecarboxylic acids:

clopyralid, dithiopyr, picloram, thiazopyr, diflufenzopyr

. 0050/49248 AMENDED SHEET : : b34 Pyrimidyl ethers: pyrithiobac-acid, pyrithiobac-sodium, KIH-2023, KIH-6127, ] pPyribenzoxym b35 Sulfonamides: flumetsulam, metosulam b36 Sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron-methyl, — chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron methyl, ethoxysulfuron, flazasulfuron, halosulfuron-methyl, imazosulfuron, metsul furon-methyl, nicosulfuron, primisulfuron, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sul fometuron-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusul furon-methyl,

N-[[[4-methoxy-6-(trifluoromethyl)-1,3, 5-triazin-2-yljamino}- carbonyl]-2-(trifluoromethyl )benzenesul fonamide . sulfosulfuron, idosulfuron b37 Triazines: ametryn, atrazine, aziprotryn, cyanazine, cyprazine, : desmetryn, dimethamethryn, dipropetryn, eglinazine-ethyl, hexazinone, procyazine, prometon, prometryn, propazine, secbumeton, simazine, simetryn, terbumeton, terbutryn, terbutylazine, trietazine b38 Triazinones: ethiozin, metamitron, metribuzin b39 Triazolecarboxamides: triazofenamid b40 Uracils: bromacil, lenacil, terbacil b4l various: benazolin, benfuresate, bensulide, benzofluor, butamifos, cafenstrole, chlorthal-dimethyl (DCPA), cinmethylin, - 40 dichlobenil, endothall, fluorbentranil, mefluidide, perfluidone, piperophos, flucabazone, oxaciclomefone (MY 100)

The following list of compounds with growth-regqulatory act ivity shows examples of active ingredients which are possible from 45 amongst this group:

} 0050/49248 AMENDED SHEET

X o 7 : l-naphthylacetamide, l-naphthylacetic acid, 2-naphthyloxyacetic acid, 3-CPA, 4-CPa, ancymidol, anthraquinone, BAP, butifos: ] tribufos, butralin, chlorflurenol, chlormequat, clofencet, cyclanilide, daminozide, dicamba, dikegulac-sodium, dimethipin, chlorfenethol, etacelasil, ethephon, ethychlozate, fenoprop, 2,4,5-TP, fluoridamid, flurprimidol, flutriafol, gibberellic acid, gibberillin, guazatine, imazalil, indolylbutyric acid, indolylacetic acid, karetazan + kinetin, lactidichlor-ethyl, maleic hydrazide, mefluidide, mepiquat-chloride, naptalam, paclobutrazole, prohexadione calcium, quinmerac, sintofen, tetcyclacis, thidiazuron, triiodobezoic acid, triapenthenol, triazethan, tribufos, trinexapacethyl, uniconazole.

The list of insecticides which follows indicates examples of active ingredients which are possible:

Neonicotinoids/ chloronicotinyl compounds: imidacloprid, acetamiprid, nitenpyram, thiacloprid, thiamethoxam, tefuranitdine, organophosphates, acephate, azinphos-methyl, chlorpyrifos, dimethoate, disulfoton, fosthiazate, methamidophos, methidathion, methyl-parathion, oxydemeton-methyl, phorate, phosalone, phosmet, profemofos, trichlorfon carbamates such as alanycarb, aldicarb, benfuracarb, carbofuran, carbosulfan, furathiocarb, methomyl, oxamyl, pirimicarb, thiodicarb pyrethroids such as bifenthrin, cyfluthrin, cypermethrin, deltamethrin, esfenvalerate, fenpropathrin, lambda-cyhalothrin, permethrin, tau-fluvalinate, 40 tralomethrin, zeta-cypermethrin urea derivatives such as diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, 45 lufenuron,

. 0050/49248 AMENDED SHEET ® 8 : novaluron, triflumuron . juvenoids such as buprofezin, diofenolan, fenoxycarb, pyriproxifen, methoxyfenozide, tebufenozide various such as abamectin, spinosad, amitraz, cartap, chlorfenapyr, diafenthiuron, fipronil pyridaben, tebufenpyrad, fenazaquin, fenpyroxymate, thiocyclam, silafluofen

The list of fungicides which follows shows examples of active ingredients which are possible: sulfur, dithiocarbamates and their derivatives, such as iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethyl- : thiuram disulfides, ammonia complex of zinc : (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,N’-propylenebisdithiocarbamate), zinc (N,N’-propylenebisdithiocarbamate),

N,N’-polypropylenebis(thiocarbamoyl)disul fide; nitro derivatives, such as dinitro(l-methylheptyl )phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate, diisopropyl 5-nitroisophthalate; heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chlorocanilino)-s-triazine, 0,0-diethyl phthal imidophosphonothioate, S-amino-1-[{bis(dimethylamino)- phosphinyl |-3-phenyl-1,2,4-triazole, 2,3-dicyano-1, 4-dithicanthraquinone, 2-thio-1,3-dithiolof4,5-bjquinoxal ine, methyl 40 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(2-furyl)benzimidazole, 2-(4-thiazolyl )benzimidazole,

N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,

N-trichloromethylthiotetrahydrophthalimide, 45 N-trichloromethylthiophthalimide,

N-dichlorofluoromethylthio-N’,N’-dimethyl-N-phenylsul famide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,

: 0050/49248 AMENDED SHEET ) 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2, 5-dimethoxybenzene, . 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,

Pyridine-2-thio $eie} l-oxide, 8-hydroxyquinoline and its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4~oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5, 6-dihydro-4H-pyran-3-carboxanil ide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethyl furan-3-carboxanilide,

N-cyclohexyl-2,5-dimethyl furan-3-carboxamide,

N-cyclohexyl-N-methoxy-2, 5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine 2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl) formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane, 2,6~dimethyl-N-tridecylmorpholine and its salts, 2,6~dimethyl-N-cyclododecylmorpholine and its salts,

N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2, 6-dimethyl- morpholine, N-[3~(p-tert-butylphenyl)-2-methylpropyl piperidine, 1-[2-(2,4~-dichlorophenyl)-4-ethyl-1, 3-dioxolan-2-ylethyl }-1H-1, 2, 4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1, 3-dioxolan-2~ylethyl }-1H- 1,2,4~triazole, :

N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl )-N’-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1B-1,2,4-triazol-l1-yl)-2- butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2— butanol, (2RS, 3RS)~1-[3-(2~-chlorophenyl)-2-(4-fluorophenyl Joxiran-2-yl- methyl]-1B-1,2,4-triazole, a-(2-chlorophenyl)-a-(4-chlorophenyl)-5-pyrimidinemethanol ’ 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl )-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)aniline,

B-[4-methyl -6-(1-propynyl )pyrimidin-2-yl)aniline, N-(4-methyl - 6—cyclopropylpyrimidin-2-yl )aniline, 40 phenylpyrroles such as 4-(2,2-difluoro-1, 3-benzodioxol-4-yl )pyrrole-3—carbonitrile,

Cinnamamides such as 45 3-(4-chlorophenyl)-3-(3, 4-dimethoxyphenyl ) acryloylmorpholine,

0050/49248 AMENDED SHEET and a variety of fungicides r Such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2 ~oxycyclohexyl )-2-hydroxyethyl Jglutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-

N-(2-furoyl) -DL—alaninate, DL-N-(2, 6-dimethylphenyl)-

N-(2’-methoxyacetyl)alanine methyl ester, N-(2,6-dimethylphenyl)-

N-chloroacetyl-pD, L-2-aminobutyrolactone, :

DL-N-(2,6-dimethylphenyl )-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3, S-~dichlorophenyl)-2, 4-dioxo- 1,3-oxazolidine, 3-[3, 5-dichlorophenyl (-

S-methyl-5-methoxymethyl }-1,3-oxazolidine-2,4-dione R 3-(3,5-dichlorophenyl) -l-isopropylcarbamoylhydantoin,

N-(3,5-dichlorophenyl)-1, 2-dimethylcyclopropane- 1,2-dicarboximide, 2-cyano-[N-( ethylaminocarbonyl)-2-methoximino ] acetamide, 1-[2-(2, 4-dichlorophenyl )pentyl }-1B-1,2,4-triazole ’ 2,4-difluoro-a-(18-1,2, 4-triazolyl-l-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trif luoromethylphenyl )- 5-trif luoromethyl-3-chloro-2-aminopyridine ’ 1-((bis(4-fluorophenyl Jmethylsilyl)methyl)-1H-1,2,4-triazole ’ 2-(4-chlorophenyl)-3-cyclopropyl-1-( 18-1,2,4-triazol- l-yl)butan- 2-ol, 3-chloro-4-[4-methyl-2-(18-1,2,4-triazol- l-ylmethyl)-1,3-dioxo- lan-2-yl)phenyl 4-chlorophenyl ether, 1,3-dimethyl-5-chloro-1 +3-dimethyl-[2,3-(2,4, 4-trimethyltetra- hydrofuran)pyrazol-4 -carboxanilide), 2’,6’-dibromo-2 -methyl- 4’'-trofluoromethoxy-4-trif luoromethylthia-zole-5-carboxanilide [sic}, [2-(e4’ ~chlorophenyl )-2-chloronicotinanilide ,

N-{(R)-1-(2, 4-dichlorophenyl)ethyl)- (S)-2-cyano- 3,3-dimethylbutanamide, N- [ (R)-1-(4-chlorophenyl)ethyl]- (S)-2,2-cyclopropyl-2’,2-dichloro-3" -methylbutanamide, 3-allyloxy-1,2-benzisothiazole 1 s1-dioxide, 2, 3-benzisothiadiazole-1l-carboxylic acid thiol ester, 1,2,5, 6-tetrahydropyrrolof3,2,1-i, jlquinolin-4-one, 5-methyl-1,2, 4-triazolo(3, 4-b)benzothiazole, di-idopropyl 1,3-dithiolan-2-ylidenemalonate ’ 4-(2,2-difluoro-1, 3-benzodioxol-4-yl)pyrrole-3-carbonitrile ’

N-(i-propoxycarbonyl)-L-valine- (R)-1-(2-naphthyl)ethylamide,

N-(i-propoxycarbonyl )-L-valine- (R-(R,S)-1-(4-methylphenyl )ethyl- amide, strobilurins such as methyl 40 E-methoximinof{a-( O-tolyloxy)-o-tolyl acetate, methyl

E-2-{2-[6-( 2-cyanophenoxy ) pyr imidin-4-yloxy phenyl }-3-methoxy- acrylate, N-methyl E-methoximino {a-(2-phenoxyphenyl) acetamide ’

N-methyl E-methoximino {a-(2,5-dimethylphenoxy) -o-tolyl}- acetamide.

. * 0050/49248 [ 1 6

From amongst the class of the strobilurins, the following fungicidally active compounds of the formula I may preferably be . mentioned: y T— 2

IN

H;C [a 0} in which the substituents have the following meanings:

A is NOCH3, CHOCH;, CHCHj;

Y is 0, NH;

T is oxygen or oxymethylene; 2 1s a group X, N=C(R1)W or N=C(R!)~C(R2)=NOR3;

X is unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted hetaryl;

W is unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkenyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl or unsubstituted or substituted hetaryl;

R! is hydrogen, cyano, C;-Cg-alkyl, C1~Cs-haloalkyl,

C1-Cy4-alkoxy, C;-Cy-alkoxy-C;-Cs-alkyl, C;3-Cg¢-cycloalkyl;

R? is hydrogen, cyano, halogen, C(RY)=NOR3 or W, OW, SW or NRCW, where

R¢ is hydrogen, alkyl, alkenyl or alkynyl; 40 RY is hydrogen or alkyl;

R3 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl or unsubstituted or substituted alkynyl 45 where

. * 0050/49248 2001 786 ® 12

X is heterocyclyl which may be fully or partially halogenated and/or may carry 1 to 3 of the following radicals: cyano, Cj-C4-alkyl, C;-Cs-haloalkyl or C;-Cy-alkoxy; aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C;-Cg¢-alkyl,

C;-Cg¢-haloalkyl, C;-Cg-alkylcarbonyl, C;-Cg-alkylsulfonyl,

C1-Cg-alkylsulfoxyl, C3-Cg-cycloalkyl, C3-Cg-alkoxy,

C;-Cg¢-haloalkoxy, C;-Cg-alkoxycarbonyl, C;-Ce¢-alkylthio,

C;-Cg-alkylamino, di-C;-Cg-alkylamino, C;-Cg-alkyl- aminocarbonyl, di-C;-Cg-alkylaminocarbonyl, Ci-Cg¢-alkyl- aminothiocarbonyl, di-C;-Cg-alkylaminothiocarbonyl,

C,-Cg-alkenyl, C,-Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, hetero- arylthio, C3-Cg¢-alkynyloxy, C;-Cs-alkylenedioxy, which may be halogenated, or C(=NORd)-I';-R4’ where

Re is hydrogen or C;-Cg-alkyl;

I' is oxygen, sulfur or NRY; 1 is 0 or 1 and the cyclic groups for their part may be partially or fully halogenated and/or may carry 1 to 3 of the following substituents: cyano, nitro, hydroxyl,

C;-Cg-alkyl, C;-Cg-haloalkyl, C;-Cg-alkylcarbonyl,

C3-Cg-cycloalkyl, C;-Cg-alkoxy, C;-Ce-haloalkoxy,

C;-Cg¢-alkoxycarbonyl, C;-Cg-alkylthio, C;-Cg-alkylamino, di-C;-Ce¢-alkylamino, C;-C¢-alkenyl, C,-Cg-alkenyloxy,

C3-Cg¢—alkynyloxy and C;-Cg-alkylenedioxy which may be halogenated,

Ww is C;-Cg-alkyl, Cp-Cg-alkenyl or C;-Cg-alkynyl, where these groups may be fully or partially halogenated and/or may carry 1 to 3 of the following radicals: cyano, C;-Cg¢-alkoxy, C;-Cg¢-haloalkoxy, C;-Ce¢-alkoxy- carbonyl, C3-Cg¢-cycloalkyl, heterocyclyl, aryl or hetaryl, where the cyclic groups for their part may be partially or fully halogenated and/or may carry 1 to 3 of the following radicals: 40 cyano, nitro, C;-C4-alkyl, C;-C4-haloalkyl,

C;-C4-alkoxy, C;-Cs-haloalkoxy; or is C3-Cg-cycloalkyl, C3-Cg-cycloalkenyl or heterocyclyl, where these groups may be fully or partially halogenated and/or may carry 1 to 3 of the following radicals: 45 cyano, C;-Csg-alkyl, C;-Cs-haloalkyl or C;-Cy-alkoxy; or is aryl or heteroaryl,

Co. * 0050/49248 2001 1786 ® 13 where these radicals may be partially or fully halogenated and/or may carry one to three of the following groups: ] cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C;-Cg-alkyl,

C1-Cg¢-haloalkyl, C;-Cg-alkylcarbonyl, C;-Cg-alkylsulfonyl,

C;-Cg-alkylsulfoxyl, C;-C¢-cycloalkyl, C;-Ce¢-alkoxy,

C;-Cg-haloalkoxy, C;-Cg-alkoxycarbonyl, C;-Cg¢-alkylthio,

C;-Cg-alkylamino, di-C;-Cg-alkylamino, C;-Cg-alkyl- aminocarbonyl, di-C;-Cg-alkylaminocarbonyl, C;-Cg-alkyl- aminothiocarbonyl, di-C;-Cg-alkylaminothiocarbonyl,

C,-Cg¢-alkenyl, C,-Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy, hetero- arylthio, C3-Cg-alkynyloxy, C;-Cs-alkylenedioxy, which may be halogenated, or C(=NOR9)-I;-R4’ where

Rd is hydrogen or C;-C¢-alkyl;

I' is oxygen, sulfur or NR9; l is 0 or 1 and the cyclic groups for their part may be partially or fully halogenated and/or may carry 1 to 3 of the following substituents: cyano, nitro, hydroxyl, Ci-Cg-alkyl, C;-Cg¢-haloalkyl,

Ci-Cg-alkylcarbonyl, C3-Cg-cycloalkyl, C;-Cg-alkoxy,

C;-Cg-haloalkoxy, C;-Cg¢-alkoxycarbonyl, C;-Cg-alkylthio,

C;-Cg-alkylamino, di-C;-Cg-alkylamino, C;-Cg¢-alkenyl,

C;-Cg-alkenyloxy, C3-Cg¢-alkynyloxy and C;-Cy-alkylenedioxy which may be halogenated,

R2 is hydrogen, cyano, halogen, C(RY)=NOR3 or W, OW, SW or NRCW, where

R¢ is hydrogen, C;~Cg-alkyl, C,-Cg¢-alkenyl or Cy-Cg-alkynyl;

Rd is hydrogen or C;-Cy-alkyl; and

R3 is hydrogen, C;-Cg-alkyl, C;-C¢-cyanoalkyl, C;-Cg¢-alkenyl,

C;-Cg¢-alkynyl, Ci-Cs-alkoxy-C;-Cg¢-alkyl or C3-Cg-cyclo- alkyl-C;-C4-alkyl, where these groups may be partially or fully halogenated and the cycloalkyl groups may additionally carry 1 to 3 C;-Cg-alkyl radicals; and their salts. 40 Collective terms represent the following substituents:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: saturated, straight-chain or branched hydrocarbon radicals 45 having 1 to 4, 6 or 10 carbon atoms, for example C;-C¢-alkyl such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, l-methylbutyl,

BE ' 0050/49248 200] 1786 ® 14 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, l-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, l-methylpentyl, ) 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,l-dimethyl- butyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, l-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, l-ethyl-l-methyl- propyl and l-ethyl-2-methylpropyl;

Haloalkyl: straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above), where the hydrogen atoms in these groups may be partially or fully replaced by halogen atoms as mentioned above, for example C;-C,-haloalkyl such as chloro- methyl, bromomethyl, dichloromethyl, trichloromethyl, fluoro- methyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, l-chloroethyl, l1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-di- fluoroethyl, 2,2-dichloro-2-fluorocethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

Alkoxy: straight-chain or branched alkyl groups having 1 to 10 carbon atoms (as mentioned above) which are attached to the skeleton via an oxygen atom (-0-);

Haloalkoxy: straight-chain or branched haloalkyl groups having 1 to 10 carbon atoms (as mentioned above) which are attached to the skeleton via an oxygen atom (-0-);

Alkylthio: straight-chain or branched alkyl groups having 1 to 10 or 1 to 4 carbon atoms (as mentioned above) which are attached to the skeleton via a sulfur atom (-S-);

Alkylamino: a straight-chain or branched alkyl group having 1 to 10 carbon atoms (as mentioned above) which is attached to the skeleton via an amino group (-NH-);

Dialkylamino: two independent straight-chain or branched alkyl groups having in each case 1 to 10 carbon atoms (as mentioned above) which are attached to the skeleton via a nitrogen atom; 40

Alkylcarbomyl: a straight-chain or branched alkyl group having 1 to 10 carbon atoms (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

Co. © 0050/49248 o® 15

Alkoxycarbonyl: an alkoxy group having 1 to 10 carbon atoms (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

Alkylthiocarbonyl: an alkylthio group having 1 to 10 carbon atoms (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

Alkylaminocarbonyl: an alkylamino group having 1 to 10 carbon atoms (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

Dialkylaminocarbonyl: a dialkylamino group (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

Alkylcarbonyloxy: a straight-chain or branched alkyl group having 1 to 10 carbon atoms (as mentioned above) which is attached to the skeleton via a carbonyloxy group (-COz-);

Alkylsulfonyl: a straight-chain or branched alkyl group having 1 to 10 carbon atoms (as mentioned above) which is attached to the skeleton via a sulfonyl group (-503-);

Alkoxysulfonyl: an alkoxy group having 1 to 10 carbon atoms (as mentioned above) which is attached to the skeleton via a sulfonyl group (-502-);

Alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 6, 8 or 10 carbon atoms and a double bond in any position, for example C,;-Cg-alkenyl such as ethenyl, l-propenyl, 2-propenyl, l-methylethenyl, l-butenyl, 2~butenyl, 3-butenyl, l-methyl-l-propenyl, 2-methyl-l-propenyl, l-methyl- 2-propenyl, 2-methyl-2-propenyl, l-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, l-methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,l-dimethyl-2-propenyl, 1,2-dimethyl- l-propenyl, 1,2-dimethyl-2-propenyl, l-ethyl-l-propenyl, l-ethyl-2-propenyl, l-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 40 5-hexenyl, l-methyl-l-pentenyl, 2-methyl-l-pentenyl, 3-methyl-l-pentenyl, 4-methyl-l-pentenyl, 1l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3 pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 45 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1l-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-l-butenyl, 1,2-dimethyl- 2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-l-butenyl,

© 0050/49248 ® 16 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl- 3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl- 2-butenyl, l-ethyl-l-butenyl, l-ethyl-2-butenyl, l-ethyl- 3-butenyl, 2-ethyl-l-butenyl, 2-ethyl-2-butenyl, 2-ethyl- 3-butenyl, 1,1,2-trimethyl-2-propenyl, l-ethyl-l-methyl- 2-propenyl, l-ethyl-2-methyl-l-propenyl and l-ethyl-2-methyl- 2-propenyl;

Haloalkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any position (as mentioned above), where the hydrogen atoms in these groups may be partly or fully replaced by halogen atoms as mentioned above, in particular by fluorine, chlorine and bromine;

Alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 3 to 10 carbon atoms and a double bond in any position which is not adjacent to the hetero atom (as mentioned above), which are attached to the skeleton via an oxygen atom (-0-);

Haloalkenyloxy: unsaturated, straight-chain or branched alkenyloxy groups having 3 to 10 carbon atoms (as mentioned above), where the hydrogen atoms in these groups may be partly or fully replaced by halogen atoms, in particular by fluorine, chlorine and bromine;

Alkenylthio: unsaturated, straight-chain or branched hydrocarbon radicals having 3 to 10 carbon atoms and a double bond in any position which is not adjacent to the hetero atom (as mentioned above), which are attached to the skeleton via a sulfur atom (=5-);

Alkenylamino: unsaturated, straight-chain or branched hydrocarbon radicals having 3 to 10 carbon atoms and a double bond in any position which is not adjacent to the hetero atom (as mentioned above), which are attached to the skeleton via an amino group (=NH-); 40 Alkenylcarbonyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any position (as mentioned above), which are attached to the skeleton via a carbonyl group (-CO-);

. : 0050/49248 ® 17

Alkenyloxycarbonyl: straight-chain or branched alkenyloxy groups having 3 to 10 carbon atoms (as mentioned above) which are attached to the skeleton via a carbonyl group (-CO-);

Alkenylthiocarbonyl: straight-chain or branched alkenylthio groups having 3 to 10 carbon atoms (as mentioned above) which are attached to the skeleton via a carbonyl group (-CO-);

Alkenylaminocarbonyl: straight-chain or branched alkenylamino groups having 3 to 10 carbon atoms (as mentioned above) which are attached to the skeleton via a carbonyl group (-CO-);

Alkenylcarbonyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any position (as mentioned above), which is [sic] attached to the skeleton via a carbonyloxy group (-CO;-);

Alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 6, 8 or 10 carbon atoms and a triple bond in any position, for example C;-Cg¢-alkynyl such as ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl- 3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1,l-dimethyl- 2-propynyl, l-ethyl-2-propynyl, l-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-l-pentynyl, 3-methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, 1,l-dimethyl-2-butynyl, 1,l-dimethyl- 3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and l-ethyl-l-methyl-2-propynyl:

Haloalkynyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a triple bond in any position (as mentioned above), where the hydrogen atoms in these groups may be partly or fully replaced by halogen atoms, in particular by fluorine, chlorine and bromine;

Alkynyloxy: unsaturated, straight-chain or branched hydrocarbon 40 radicals having 3 to 10 carbon atoms and a triple bond in any position which is not adjacent to the hetero atom (as mentioned above), which are attatched to the skeleton via an oxygen atom (~0-); 45 Haloalkynyloxy: unsaturated, straight-chain or branched alkynyloxy groups having 3 to 10 carbon atoms (as mentioned above), where the hydrogen atoms in these groups may be partly or

Co. © 0050/49248 fully replaced by halogen atoms as mentioned above, in particular by fluorine, chlorine and bromine;

Cycloalkyl: monocyclic, saturated hydrocarbon groups having 3 to 6, 8, 10 or 12 carbon ring members, for example C3-Cg-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;

Cycloalkoxy: monocyclic, saturated hydrocarbon groups having 3 to - 12 carbon ring members (as mentioned above) which are attached to the skeleton via an oxygen atom (-0-);

Cycloalkylthio: monocyclic, saturated hydrocarbon groups having 3 to 12 carbon ring members (as mentioned above) which are attached to the skeleton via a sulfur atom (-S-);

Cycloalkylamino: monocyclic, saturated hydrocarbon groups having 3 to 12 carbon ring members (as mentioned above) which are attached to the skeleton via an amino group (-NH-);

Cycloalkylcarbonyl: monocyclic, saturated hydrocarbon groups having 3 to 12 carbon ring members (as mentioned above) which are attached to the skeleton via a carbonyl group (-CO-);

Cycloalkoxycarbonyl: a monocyclic cycloalkoxy group having 3 to 12 carbon ring members (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

Cycloalkylthiocarbonyl: a monocyclic cycloalkylthio group having 3 to 12 carbon ring members (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-); saturated or partially unsaturated cyclic radical which, in addition to carbon atoms, may contain hetero atoms from the group consisting of oxygen, sulfur or nitrogen as ring members: cycloalkyl having 3 to 12 carbon ring members as mentioned above or 5- or 6-membered heterocycles (heterocyclyl) containing, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or 40 sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetra- hydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 45 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,

. ) 0050/49248

L 19 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4~thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-y1, . l,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-y1, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-y1, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydro- thien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2,3-pyrrolin-2-yl, 2,3-pyrrolin-3-yl, 2,4-pyrrolin-2-yl, 2,4-pyrrolin-3-yl, 2,3-isoxazolin-3-yl, 3,4-isoxazolin-3-yl, 4,5-isoxazolin-3-yl, 2,3-isoxazolin-4-yl, 3,4-isoxazolin-4-yl, 4,5-isoxazolin-4-yl, 2,3-isoxazolin-5-yl, 3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl, 3,4-iso- thiazolin-3-yl, 4,5-isothiazolin-3-yl, 2,3-isothiazolin-4-yl, 3,4-isothiazolin-4-yl, 4,5-isothiazolin-4-yl, 2,3-iso- thiazolin-5-yl, 3,4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl1, 2,3-dihydropyrazol-l-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydro- pyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydro- pyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydro- pyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydro- oxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-y1l, 3,4-dihydro- oxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydro- pyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-tetrahydro- pyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydro- pyrazinyl, 1,3,5-tetrahydrotriazin-2-yl and 1,2,4-tetrahydro- triazin-3-yl;

Aryl: a mono- to tricyclic aromatic ring system containing 6 to 14 carbon ring members, for example phenyl, naphthyl and anthracenyl;

Aryloxy: a mono- to tricyclic aromatic ring system (as mentioned above) which is attached to the skeleton via an oxygen atom (=0-); 40

Arylthio: a mono- to tricyclic aromatic ring system (as mentioned above) which is attached to the skeleton via a sulfur atom (-S-);

Arylamino: a mono- to tricyclic aromatic ring system (as 45 mentioned above) which is attached to the skeleton via an amino group (-NH-);

. ) 0050/49248 200

KJ 20

Arylcarbonyl: a mono- to tricyclic aromatic ring system (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

Aryloxycarbonyl: a mono- to tricyclic aryloxy group (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

Arylthiocarbonyl: a mono- to tricyclic arylthio group (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

Arylaminocarbonyl: a mono- to tricyclic arylamino group (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO~);

Arylcarbonyloxy: a mono- to tricyclic aromatic ring system (as mentioned above) which is attached to the skeleton via a carbonyloxy group (-CO;-);

Arylcarbonylthio: a mono- to tricyclic aromatic ring system (as mentioned above) which is attached to the skeleton via a carbonylthio group (-C0S-);

Arylcarbonylamino: a mono- to tricyclic aromatic ring system (as mentioned above) which is attached to the skeleton via a carbonylamino group (-CONH-);

Arylsulfonyl: a mono- to tricyclic aromatic ring system (as mentioned above) which is attached to the skeleton via a sulfonyl group (-S02-);

Aryloxysulfonyl: a mono- to tricyclic aryloxy group (as mentioned above) which is attached to the skeleton via a sulfonyl group (-502-); aromatic ring system which, in addition to carbon ring members, may contain hetero atoms from the group consisting of oxygen, sulfur and nitrogen: aryl as mentioned above or mono- or bicyclic 40 heteroaryl, for example - S5-membered hetaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom: 5-membered hetaryl ring groups which, besides carbon atoms, can contain one to four nitrogen atoms or one to three 45 nitrogen atoms and one sulfur or oxygen atom as ring members, for example, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl,

: ) 0050/49248

L 21 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, . 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl; - benzo-fuzed 5-membered hetaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom: 5-membered hetaryl groups which, besides carbon atoms, can also contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members and in which two adjacent carbon ring members or one nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group; - S~-membered hetaryl, bonded via nitrogen and containing one to four nitrogen atoms, or benzo-fuzed S5-membered hetaryl, bonded via nitrogen and containing one to three nitrogen atoms: S5-membered hetaryl groups which, besides carbon atoms, can contain one to four nitrogen atoms, or one to three nitrogen atoms, respectively, as ring members and in which two adjacent carbon ring members or one nitrogen and an adjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diyl group, these rings being bonded to the skeleton via one of the nitrogen ring members; - 6-membered hetaryl containing one to three, or one to four, nitrogen atoms: 6-membered hetaryl ring groups which, besides carbon atoms, can contain one to three, or one to four, nitrogen atoms as ring members, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

As for the remaining substituents, these correspond to the substituents described in W0/15552.

Other suitable fungicidal crop protection active ingredients are: 40 (+)—cis—1—(4—chlorophenyl)—2—(18-1,2,4—triazol-1-yl)cyclohep- tanol, metsulfovax, cyprodinil, methyl (E)—2—{2—[ 6—(2—cyanophenoxy)pyrimidin—4—yloxy ]phenyl }—3—methoxy- acrylate and the azole active ingredients

N—propyl-N—[2,4,6—trichlorophenoxy)ethyl)imidazole~l—carboxamide 45 (prochloraz), (2)—2—(1,2,4—-triazol—-1-ylmethyl )—2—(4—fluorophenyl)-3—(2— chlorophenyl)oxirane (epoxiconazole),

} } 0050/49248 AMENDED SHEET

CL ® 22 1-butyl-1-(2,4—dichlorophenyl )—2—(1,2,4—triazol-l-yl)ethanol (hexaconazole), 1—[(2—chlorophenyl methyl )~1—(1,1-dimethyl )—2— } (1,2,4-triazol-l1-ylethanol), 1-(4—fluorophenyl )—1—( 2—fluorophenyl )—2—(1, 2, 4-triazol—-1-yl)- ethanol (flutriafol), (RS)—~4—(4—chlorophenyl )—2—phenyl-2—(18-1, 2, 4—triazol-l1-ylmethyl)— butyronitrile, 1-[(2 RS, 4 RS; 2 RS, 4 SR)~4-bromo—2—(2,4— dichlorophenyl ) tetrahydrofurfuryl ]—18-1,2,4—triazole x 3-(2,4-dichlorophenyl )—2—( 18-1, 2, 4-triazol—1-yl )quinazol in—4— (3H)-one, (RS)-2,2-dimethyl—-3—(2—chlorobenzyl )—4—(1B-1, 2, 4-triazol—1-yl)- butan—3-o0l, bitertanol, triadimefon, triadimenol, bromuconazole, cyproconazole, dichlobutrazole, difenoconazole, diniconazole, etaconazole, fluquinconazole, imibenconazole, propiconazole, flusilazole, tebucomazole, imazalil, penconazole, tetraconazole, trifilumizol, metconazole, fluquinconazole, fenbuconazole, triticonazole.

The fungicidal crop protection active ingredients are preferably from the group consisting of: tridemorph, fenpropimorph, fenpropidine and the azole active ingredients, it being possible for one or more active ingredients amongst the group consisting of tridemorph, fenpropimorph and fenpropidine to be present in the soil-applied CR granules according to the invention.

The following are preferred amongst the azole active ingredients: prochloraz, epoxiconazole, hexaconazole, cyproconazole, difenoconazole, propiconazole, flusilazole, diniconazole, triticonazole and tebuconazole, the use of epoxiconazole being especially advantageous.

Also suitable are valinamide active ingredients, preferably:

Nl-{1-(4-chlorophenyl) -1-ethyl}-N2-isopropoxycarbonyl-L-valinamide,

Nl{1-(4-methylphenyl)- l1-ethyl]}-N2-jisopropoxycarbonyl-L-valinamide,

Nl-{1-(4-methoxyphenyl) -l-ethyl}-N2-isopropoxycarbonyl-L valinamide,

Nl1-[1-R-(2-naphthyl) -l-ethyl]}-N2-isopropoxycarbonyl-L-valinamide.

Preferred amongst the group of the resistance activators is Bion® 40 (5-methyl benzo{1,2,3)thiadiazole-7-carbothiocate).

The following compounds of formula I1I are preferably employed from amongst the group of the salicylates: .

. ) 0050/49248

J 23

OR® O 10 (im (Rn in which R? is: n-, i- or tert-C;-Cg-alkyl, C;-Cg-alkoxyalkyl or Ci-Cg-haloalkyl, n- or i- C;-Cg-alkylcarbonyl, preferably acetyl, propionyl, benzoyl, C;-Cg-alkylbenzoyl, C;-Cg-haloalkylbenzoyl,

C;-Cg-~alkoxybenzoyl or hydrogen, hydroxycarbonyl-C;-Cs-alkyl,

C,-C4-alkoxycarbonyl-C;-C4-alkyl,

R10 can be hydroxyl, n- or i- or tert- Ci-Cg-alkyloxy,

C.-Cg-haloalkyloxy, C:-Cy-alkoxy-C;-Cs-alkoxy, furthermore amino,

C;-Cg-alkylcarbonylamino or substituted or unsubstituted arylcarbonylamino or, preferably, benzoylamino, C;~Cg-alkylamino, di-C;-Cg-alkylamino, substituted (1-3 substituents selected from the group consisting of halogen, CN, NO, OH, NH,;, COyH, CONHp,

C,-C4-alkyl, C;-Cyg-haloalkyl, C;-Cy-alkoxy, C;-Cs~haloalkoxy,

C;-C4-alkoxycarbonyl, C;-Csg-alkylamino, di-C;-C4-alkylamino) or unsubstituted arylamino (in particular phenylamino).

Rll independently of one another can be: hydrogen, fluorine, chlorine or iodine, n- or i- or tert-

C,-Cg-alkyl, C;-Cg-alkoxyalkyl or C;-Cg-haloalkyl, furthermore an aryl radical of formula IV, (IV) (R'm 40 which is unsubstituted or mono- or up to trisubstituted and in which the index m or n can be 0-3 and the radical R12 has the meaning given for R11. 45 Especially preferred are the compounds:

Claims (22)

- 005 0/49248 AMENDED SHEET . ® 59 CLAIMS

1. soil-applied CR granules obtainable by applying an active-ingredient-comprising coating to a solid carrier in a fluidized bed with a defined heat input adjustable to 6000 to 25,000 KJ/KG of coating polymer.

2. Soil-applied CR granules as claimed in claim 1 with an active-ingredient-comprising coating of

0.1-25% by weight of one or more active ingredients 1-40% by weight of one or more coating polymers 0-60% by weight of one or more additives, the total of the % by weight of the compounds in the coating being 100% by weight.

3. Soil-applied CR granules as claimed in claim 2 comprising, as coating polymer, a dispersion from amongst the following groups: butyl acrylate/styrene copolymers, copolymer dispersions of acrylic and methacrylic esters, polyethylene wax emulsions, palyesters composa2d of the following units: to 50 molt dimethyl terephthalate - approx. 50 mol% adipic acid + 150 molt 1,4-butanediol + trace elements, mixture of 10-95% polyvinyl acetate + 5-90% n-vinylpyrrolidone-comprising fsie} polymers, ethylene/methacrylic acid zinc salt.

4. ©Soil-applied CR granules as claimed in claim 3 comprising, as coating polymer, at least one from amongst the group of the biodegradable polyesters.

5. Soil-applied CR granules as claimed in claim 1 comprising, as active ingredient, at least one fungicidal compound of the k 1 formula I from amongst the class of the strobilurins. T—22 ) 40 Y ~~ H3C ~ NN, 0 in which the substituents have the following meanings: 45 A is NOCH;, CHOCH3, CHCHj;

0050/49248 AMENDED SHEET Y is O, NH; . iy is oxygen or oxymethylene; Z is a group X, N=C(R!)W or N=C(R!)-C(R2)=NOR3; X is unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl, unsubstituted or substituted hetaryl; — Ww is unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted cycloalkenyl, unsubstituted or substituted heterocyclyl, unsubstituted or substituted aryl or unsubstituted or substituted hetaryl; Rl is hydrogen, cyano, C;-C4-alkyl, C;-C4-haloalkyl, C1-C4-alkoxy, C;-Cq-alkoxy-C,-C4-alkyl, C3-Cg¢-cycloalkyl;

. 20 R? is hydrogen, cyano, halogen, C(RY)=NOR3 or W, OW, SW or NRW, where R€ is hydrogen, alkyl, alkenyl or alkynyl; Re is hydrogen or alkyl; R} is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl or unsubstituted or substituted alkynyl, or a salt thereof.

6. Soil-applied CR granules as claimed in any one of claims 1-5, comprising an active ingredient from the group of the systemically acting strobilurins, the azoles or the salicylates.

7. Soil-applied CR granules as claimed in any of claims 1-5, 40 comprising, as active ingredient, 5-methyl benzo(1,2,3)thiadiazole-7-carbothiocate.

8. Soil-applied CR granules as claimed in claim 1, comprising, as carrier, water-soluble, water-insoluble or biodegradable 45 granules.

. N 61

9. A process for the preparation of soil-applied CR granules as claimed in any one of claims 1-8, which comprises applying,

C. to a carrier, first the active ingredient and then the coating comprising at least one coating polymer and, if S appropriate additives in a fluidized bed, micropores being generated in the coating by abrasion or by the directed addition of water-soluble additives (lime, starch).

10. A method for controlling phytopathogenic fungi, undesired vegetation, undesired attack by insects and/or for regulating the growth of plants, which comprises allowing Soil-applied CR granules as claimed in any one of claims 1 to 9 to act on plants, their environment or on seed.

11. The use of the soil-applied CR granules as claimed in any one of claims 1-8 or obtained as claimed in claims 9 and 10 for controlling phytopathogenic fungi, undesired vegetation, undesired attack by insects and/or for regulating the growth of plants.

12.Soil-applied CR granules as claimed in any one of claims 1 to 8, substantially as hereinbefore described or exemplified.

25 . . . . . .

13.Soil-applied CR granules including any new inventive integer or combination of integers, substantially as herein described. Ld

14.A process according to the invention for the preparation of soil-applied CR granules, substantially as hereinbefore described or exemplified.

15.A process for the preparation of soil-applied CR granules including any new inventive integer or combination of integers, substantially as herein described. 40

16.A method according to the invention for controlling phytopathogenic fungi, undesired vegetation, undesired attack by insects and/or for regulating the growth of 45 plants, substantially as hereinbefore described or exemplified.

— . AMENDED SHEET . ® 6la

17.A method for controlling phytopathogenic fungi, undesired vegetation, undesired attack by insects and/or for regulating the growth of plants including any new inventive integer or combination of integers, substantially as herein described.

18.The use of the scil-applied CR granules as claimed in claim 11, substantially as hereinbefore described or exemplified.

19.The use of the soil-applied CR granules including any new inventive integer or combination of integers, substantially as herein described.

20.Soil-applied CR granules as claimed in any one of claims 1 to B and 12 to 13 whenever supplied with instructions for the use thereof in controlling phytopathogenic fungi, undesired vegetation, undesired attack by insects and/or for regulating the growth of plants.

2]1.S50il-applied CR granules as claimed in claim 20 when the instructions are in printed or written form.

22.Soil-applied CR granules as claimed in claim 21 supplied in a package or container having the said instructions provided therein or thereon. i

0050/49248

Soil-applied granules with controlled release of active ingredient(s) (soil-applied CR granules) S

Abstract The present invention relates to soil-applied CR granules obtainable by applying an active-ingredient-comprising coating to

@ solid carrier in a fluidized bed, to a process for the preparation of these soil-applied granules, and to a method for controlling phytopathogenic fungi, undesired vegetation, undesired attack by insects and/or for regulating the growth of plants using the soil-applied CR granules according to the invention.

40