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(11) Patent Number: KE 404

(73)0wner:BAYER CROPSCJENCE AG  of • Alfred-Nobel-Sir. 50,40789 Monbeim , Germany
           
(ll)Application Number: KE/P/2008/ 000716       

(72) Inventor:THJELERT, Wolfgang  of Buschweg 69, 51519 Odenthal, Germany; BRUEGGEN, Kai-Uwe of Rbeindorfer Str. 4, 50737 Koln, Germany; BAILO- SCHLEJERMACHER, Isidro ofLohrstr. 24,51371 Leverkusen, Germany; VERMEER, Ronald ofEulenkamp 1, 51371 Leverkusen, Germany and HUNGENBERG, Heike ofLouveciennesstr. 2a, 40764 Langenfeld, Germany.

(22) Filing Date:26/0812006   
       
(30) Priority data:10 2005 042 880.0  09/0912005  DE           
       
(86)  PCT data     PCT/EP06/008387    26/08/2006 wo 2007/028517 A2    15/03/2007       

(74) Agent/address for correspondence:Kaplan & Stratton Advocates, P.O. Box 40111-00100,Nairobi

(54)    Title: USE OF CNI-OD FORMULATIONS FOR CONTROLLING WHITE FLY

(57)    Abstract: The invention relates to a method for controlling the eggs and nymphal stages of white fly by spray-applying oil-based suspension concentrates. Said concentrates comprise at least one insecticide from the group of neonicotinyls, at least one penetration enhancer from the group of alcohol ethoxylates, at least one vegetable oil, at least one nonionic surfactant and optionally one or more additives

Oil-based suspension concentrates
The present invention relates to new, oil-based suspension. &oncentrates of aper-chemical active compounds, a process for the preparation of these formulations and

5    their use for the application of the active compounds contained.


Nwnerous  anhydrous  suspemion  concentrates  of agrochemical  active  compounds

have already been disclosed. Thus, EP-A 0 789 999 describes formulations of this

type which, in _addition to active compound and oil, contain a mixture of various

10    swfactants, - among them also those which serve as penetration promoters-, and a hydrophobized alwno-layer silicate as a thickening agent. The stability of these

preparations is good. It is disadvantageous, however, that a thickening agent is compulsorily present, because the preparation is more complicated on account of this. Moreover, the thickening agent in each case absorbs some of the amount of
15    penetration promoter added, which is therefore not available for its real function.


Furthermore, US-A 6 165 940 already discloses non-aqueous suspension concen-trates in which, apart from agrochemical active compound, penetration promoter and surfactant or surfactant mixture. an organic solvent is present, suitable solvents of

20    this type also being paraffin oil or vegetable oil esters. The biological activity and the stability of the spray liquors which can be prepared from these formulations by diluting with water, however, is not always adequate.

New oil-based suspension concentrates have now been found, which consist of

25

at least one agrochemical  active compound  which is  solid  at room  tem-

perature,


at least one E_enetration promoter,

30
 

at least one vell!'table oil,

    at least one non-ionic surfactant or dispersing aid and/or at least one anionic
    surfactant or dispersing aid and
5    ootionally one or more additives from the group consisting of the emulsifying
    ~the antifoam a~ts. th«u!:~servatives. the antioxidants, the colourants
    and/or the inert filling materials.
    It has furthermore been found that the oil-based suspension concentrates according to
10    the invention can be prepared by mixing
    at least one agrochemical  active compound  which  is  solid at room  tem-
    perature,
15    at least one penetration promoter,
    at least one vegetable oil,
    at least one non-ionic surfactant or dispersing aid and/or at least one anionic
20    surfactant or dispersing aid and
    optionally one or more additives from the groups consisting of the emul-
    sifying agents, the antifoam agents, the preservatives, the antioxidants, the
    colourants and/or the inert filling materials
25   
    with one another and then optionally grinding the resulting suspension.
    Finally, it has been found that the oil-based suspension concentrates according to the
    invention are very highly suitable for  the  application of the agrochemical active
30    compounds contained to plants and/or their habitat.
 

It is to be indicated as extremely surprising that the oil-based suspension concentrates

according  to  the  invention have  a very good stability,  although they  contain  no

thickening agent. It is also unexpected that they exhibit a marlcedly better biological

activity than the previously known formulations having the most similar compo-

S    sition. Otherwise, the oil-based suspension concentrates accordin_g_ tQ the invention._ with resOect to their activity, surprisingly also excel analogous preparations which in addition to• the other components, contain either only penetration promoter or only ve_g_etable oil. Such a synergistic effect could not be foreseen on the basis of the prior art described above.

10

The oil-based suspension concentrates according to the invention_ arc also distin-

guished by a number of advantages_. 'fb1Js their preparation is less complicated than

the preparation of corresponding fonnulations in which thickening agents are present.

It is furthermore advantageous that on diluting the concentrates according to the

15    invention with water neither a significant formation of cream nor a troublesome formation of flocks occurs, which is frequently the case with corresponding pre-viously known preparatioos. Finally, the formulatioll8 according to the invention

favour  the  biological  activity  of  the  active  components  contained.  so  that  in

-r:-ompanson to conventional preparations either a higher activity is achieved or less

20    active compound is necessary.


Solid, agrochemical active compounds are to be und=tood in the present com-position as meaning all substances customary for plant treatment, whose melting
point is above 20°C. Fungicides, bactericides, insecticides, acaricides, nematicides,

25    molluscicides, herbicides, plant growth regulators, plant nutrients and repellents may preferably be mentioned.

Examples of fungicides which may be mentioned are:


30    2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2',6'-<libromo-2-methyl-4'-trifluoro-methoxy-4'-trifluoromethyl-1,3-thiazol.,.S-carboxanilide; 2,6-dicltloro-N-(4-trifluoro-

methylbenzyl)-benzamide; (E)-2-methoximino-N-methyl-2-(2-phenoxyphenyl)-acet-amide; 8-hydroxyquinoline sulphate; methyl (E)-2-{2-[6-(2-cyanophenoxy)-py-rimidin-4-yloxy]-phenyl)-3-methoxyacrylate; methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]-acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine,
azaconazole,

benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S, bromu-conazole, bupirimate, buthiobate,

10    calcium polysulphide, captafol, captan, carbendazim, carboxin, quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cypro-conazole, cyprofuram, carpropamide,

dichlorophen,  diclobutrazole,  dichlofluaoid,  diclomezin,  diclorao,  diethofencarb,

15    difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine, drazoxolon,

edifenphos, epoxyconazole, ethirimol, etridiazole,

20    fenarimol, fenbuconazole, fenfurarn, fenitropao, fenpiclonil, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furmecyclox, fenhexarnide,

25    guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iprobenfos  (lliP),  iprodion,  isoprothiolan,

30    iprovalicarb,
 

kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate,

copper  oxychlotide,  copper  sulphate,  copper  oxide,  oxine-copper  and Bordeaux

mixture,

mancopper,  mancozeb,  maneb,  mepanipyrim,  mepronil,  m.etalaxyl,  metconazole,

methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil,

nickel dimethyldithiocarbarnate, nitrothal-isopropyl, nuarimol,

10    ofurace, oxadixyl, oxamocarb, oxycarboxine,

pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxine, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyra-zophos, pyrifenox, pyrimethanil, pyroquilon,

15

quintozene (PCNB), quinoxyfen,

sulphur and sulphur preparations,

20 ~buconazo1e. tecloftalarn, tecnazene, tetraconazole, thiabendazole, thi"YQfe!h JhiQ- _ phanate-methyl. !hiram. to1clophos-methy1 toly!fluanid triadimefon. triadimenol. tri-azoxide, trichlarnide, tricyclazole, tridemorph, trifluntizole, trifotin, triticonazole, trifloxystrobin,

25    validamycin A, vinclozolin, zineb, ziram and

2-[2-(1-chloro-cyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-

30    [1,2,4]-triazole-3-thione.

Examples of bactericides which may be mentioned are:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbarnate, kasugarnycin, octhilinon, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclofta-lam, copper sulphate and other copper preparations.

Examples of insecticides, acaricides and nematicides which may be mentioned are:

abarnectin,    acephate,   acriuathrin,   a!anycarb,   aldicarb,   alpharaethtin,   amitraz,

10    avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, azocyclotin,

Bacillus thuringiensis, 4-bromo-2-(4-chlorphenyl)-1-( etho_=ethyl)-5-(lrifluorome-thyl)-IH-pyrrole-3-carbonilrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthtin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocarboxine,

15    butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, chloethocarb, chloretoxyfos, chlorfenvinphos, chlorfluazuron, chlormephos, N-[(6-chloro-3-

pyridinyl)-methyl]-N'-cyano-N-methyl-ethaneintidamide,  chlorpyrifos,  chlorpyrifos

20    M, cis-resmethtin, clocythtin, clofentezin, cyanophos, cyclo_prothtin, cyfluthtin, cyhalothtin, cyhexatin, cypermethrin, cyrornazin,

deltamethrin,  demeton-M,  demeton-S,  demeton-S-methyl,  diafenthiuron,  diazinon,

dichlofenthion,  dichlorvos,  dicliphos,  dicroto_phos,  diethion,  diflubenzuron,  di-

25    methoate,

_Jjrnefbylyiuphns dimatbjon  djg111fpton

emamectin.    esfen   valerate,   ethiofencarb.   ethion,   ethofenprox,   ethoprophos,

30    elrimphos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, feoobucarb, fenothiocarb, fenoxycarb, fenpropatbrin, fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazuron, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fono-phos, formothion, fosthiazate, fubfenprox, furathiocarb,

HCH, heptenophos, hexaflurnuron, hexythiazox,

imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion. ivermectin,

lambda-cyhalothrin, lufenuron,

10

malathion, mecarbam, mevinphos, mesulfenphos, metaldehyde, methacrifos, metha-midophos, methidathion, methiocarb, methomyl, metolcarb, milbemecti.n, mono-crotophos, moxidectin,

15    naled, NC 184, nitenpyrarn,

omethoate, oxamyl, oxydemethon M, oxydeprofos,

parathion A, parathion M, permethrin, phenthoate, phorate, phosalon, phosmet, phos-

20    pharnidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenophos, prome-carb, propaphos, propoxur, prothiophos, prothoate, pyrnetrozine, pyrachlophos, pyri-daphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen,

quinalphos,

25
salithion, sebufos, silafluofen, snlfotep, sulprofos,

tebufenozide, tebufenpyrad, tebupirimiphos, teflubeozuron, tefluthrin, temephos, ter-barn, terbufos, tetrachlorvinphos, thiacloprid, thiafenox, thiamethoxarn, thiodicarb,

30    thiofaoox, thiomethon, thionazine, thuringiensin, tralomethrin, transflutbrin, triarathen, triazophos, triazuron, trichlorfon, triflurnuron, trimethacarb,


Examples of molluscicides which may be mentioned are metaldehyde and methi<>-

carb.

Examples of herbicides which may be mentioned are:

aoilides, such as, for example, dillufeoican aod propaoil; arylcarboxylic acids, such as, for example, dichlorpicolinic acid, dicaroba aod picloraro; aryloxyalkanoic acids, such as, for example, 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA. MCPP and
10    triclopyr;  aryloxy-pheooxy-alkaooic  acid  esters,  such  as,  for  exarople,  diclofop-

.methyl. fenoxaprop-ethyl. fluazifop-butyl, haloxyfop-methyl -~ ql\izalofop-ethyl; azinones, such as, for example, chloridazon and norflurazon; carbamates, such as, for

example,    chlorpropharo,    desmedipharn,    phenmedipharo    and    propharo; chloroacetanilidea, such as, for example, alachlor, acetochlor, butachlor, metazachlor, IS       metolachlor,  pretilachlor  aod propachlor;  dinitroaoilines,  such  as,  for  example, oryzalin,  peodimethalin  and  trifluralin;  dipheoyl  ethers,  such  as,  .for  example, acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen aod oxyfluorfen;

ureas, such as, for example, chlortoluron, diuron, fluometuron, isoproturon, linuron

aod    methabenzthiazuron;  hydmxylaroines,  such  as,  for  example,  alloxydim,

20    clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, such as, for example, imazethapyr, imazarnethabeoz, imazapyr aod imazaquin; nitriles, such as, for example, bromoxynil, dichlobeoil aod ioxynil; oxyacetarnides, such as, for example, mefenacet; sulphonyloreas, such as, for example, arnidosulfuron, beosulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-

25    methyl, nicosulfumn, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron aod tnbenuron-methyl; thiocarbamates, such as, for example, butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, such as, for example, atrazine, cyaoazine, simazine, simetryne, terbutryne
and terbutylazine;  triazinones,  such as,  for  example.  hexazin~ metamitron  and

30    metribuzin; others, such as, for example, aminotriazole, benfuresate, bentazone, cin-methylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofurnesate, fluor<>-

chloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane. In addition, 4-anaino-N-(l,l-dimethylethyl)-4,5-dihydro-3-(l-methylethyl)-5-oxo-IH-1,2,4-triazole-l-carboxamide and 2-((((4,5-dihdydro-4-methyl-5-oxo-3-propoxy-lH-1,2,4-triazol-l-yl)carbonyl)anaino)sulfonyl) methyl
benzoate may be mentioned.

Examples of plant growth regulators which may be mentioned are chlorocholine chloride and ethephon.

10    Examples of plant nutrients which may be mentioned are customary inorganic or organic fertilizers for supplying plants with macro- and/or micronutrients.

Examples of repellents which may be mentioned are diethyl-tolylarnide, ethylhexane-

diol and buto-pyronoxyl.

15

Suitable penetration promoters in the present composition are all those substances

which are customarily employed in order to improve the penetration of avochemical

active compounds into plants. Alkanol alkoxylates of the formula

20    R-0-(-AO)mH    (I)

in which

R    represents straight-chain or branched alkyl having 4 to 20 carbon atoms,

25

AO    represents an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical, or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals and

30    m    represents numbers from 2 to 30,

are preferred.

A particularly preferred group of penetration promoters are alkanol alkoxylates of the

formula

R-0-(-E0-)0-H    (Ia)

in which

10    R has the meaning indicated above,

EO represents -CH2-CHrO- and

n    represents numbers from 2 to 20.

15

A further particularly preferred group of penetration promoters are alkanol alkoxy-

lates of the formula

R-0-(-EO-)p-(-PO-)q-H    (!b)

20

in which

R    has the meaning indicated above,



PO    represents  -cH.--TH-0- •

CH3

p    represents numbers from I to 10 and

q    represents numbers from I to 10.

A further particularly preferred group of penetration promoters are alkanol alkoxy-lates of the formula

R-0-(-PO-),-(EO-),-H    (lc)

in which

R    has the meaning indicated above,

10

EO    represents -CHrCHrO-.

PO    represents  -CH;-TH-0- ,

CH3

represents numbers from I to 10 and

15

represents numbers from I to 10.

A further particularly preferred group of penetration promoters are alkanol alkoxy-lates of the formula

20

in which

represents numbers from 8 to 13

25

and

represents numbers from 6 to 17 .

In the formulae indicated beforehand

R    preferably represents buty~ i-buty~ n-pentyl, i-penty~ neopentyl, n-hexy~ i-hexyl, n-octyl, i-octyl, 2-ethyl-hexyl, nonyl, i-nonyl, decyl, n-dodecyl, i-dodecyl, Iaury!, myristyl, i-tridecyl, trimethyl-nonyl, palmityl, stearyl or eicosyl.


An example of an alkanol alkoxylate of the formula (lc) which may be mentioned is

2-ethyl-hexyl alkoxylate of the formula

in which

EO    represents -CHrCHrO-,

15

PO    represents  -CH,1H-o-  and

CH3

the numbers 8 and 6 are average values.

Particularly preferred alkanol alkoxylates of the formula (!d) are compounds of this 20 formula in which

represents numbers from 9 to 12 and

u    represents numbers from 7 to 9.

25

The above formulae give a general definition of the alkanol alkoxylates. These sub-stances are mixtures nf substances of the type indicated having different chain

lengths. For the indices, therefore, average values are calculated which can also differ

from integers.

By way of example, an alkanol alkoxylate of the formula (!d) may be mentioned, in which


represents the average value 10.5 and

u    represents the average value 8.4.

10

The alkanol alkoxylates of the formulae indicated are known or can be prepared by known methods (cf. WO 98-35 553, WO 00-35 278 and EP-A 0 68! 865).

Possible  vegetable oils  are  all  oils  which  can customarily be  employed  in agro-

15    chemical agents and can be obtained from plants. By way of example, sunflower oil, rapeseed oil, olive oil, castor oil, colza oil, maize germ oil, cottonseed oil and soya bean oil may be mentioned.

The oil-based suspension concentrates according to the invention contain at least one

20    non-ionic surfactant or dispening aid and/or at least one anionic surfactant or dispersing aid.

Suitable non-ionic surfactants or dispersing aids are all substances of this type which

can customarily be employed in agrochemical agents. Preferably, polyethylene oxide-

25    polypropylene oxide block copolymers, polyethylene glycol ethers of linear alcohols, reaction products nf fatty acids with ethylene oxide and/or propylene oxide, further-more polyvinyl alcohol, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and
polyvinylpyrrolidone, and copolymers of (meth)acrylic acid and (meth}-acrylic acid

esters,  furthermore  alkyl  ethoxylates  and  alkylaryl  ethoxylates,  which  can  be

30    optionally phosphated and optionally neutralized with bases, where sorbitol ethoxy-


lates may be mentioned by way of example, and polyoxyalkylenamine derivatives

may be mentioned.

Possible anionic surfactants are all substances of this type which can customarily be

employed in agrochentical agents. Alkali metal and alkaline earth metal salts of alkylsulphonic acida or alkylarylsulphonic acida are preferred.

A farther preferred group of aoionic surfactants or dispersing aids are salts of poly-styrenesulphonic acida, salts of polyvinylsulphortic acids, salts of naphthalene-

10    sulphonic acid-fonnaldehyde condensation products, salts of condensation products of naphthalenesulphonic acid, phenolsulphortic acid and formaldehyde, and salts of lignosulphonic acid, which are not very soluble in vegetable oil.

Suitable  additives  which  can  be  contained  in  the  formulatiorts  according  to  the

15    invention are emulsifiers, antifoam agents, preservatives, antioxidants, colourants and inert filling materials.

Preferred emulsifiers are ethoxylated nonylphenols, reaction products of alkylphenols

with ethylene oxide and/or propylene oxide, ethoxylated arylalkylphenols, forther-

20    more ethoxylated and propoxylated arylalkylphenols, and sulphated or phosphated arylalkyl ethoxylates or -ethoxy-propoxylates, where sorbitan derivatives, such aa polyethylene oxide-sorbitan fatty acid esters and sorbitan fatty acid esters, may be mentioned by way of example.

25    Suitable antifoam substances are all substances which can customarily be employed in agrochentical agents for this purpose. Silicone oils and magnesium stearate are preferred.

Possible  preservatives  are  all substances  which  can customarily  be employed  in

30    agrochemical agents for this purpose. Examples which may be mentioned are Preventol® (Bayer AG) and Proxel®.
 

Suitable antioxidants are all substances which can customarily be employed in agrochemical agents for this purpose. Butylhydroxytoluene is preferred.

Possible colourants are all substances whicb can customarily be employed in agrochemical agents for this purpose. Titanium dioxide, carbon black, zinc oxide and blue pigments, and Permanent Red FGR may be mentioned by way of example.

.  Suitable inert filling materials are all substances which can customarily be employed

10    in agrochemical agents for this purpose, and which do not function as thickening agents. Inorganic particles, such as carbonates, silicates and oxides and also organic substances. such as urea-formaldehyde condensates, are preferred. Kaolin, rutile, silica ("highly disperse silicic acid"), silica gels, and natural and synthetic silicates, moreover talc, may be mentioned by way of example.

15

The content of the individual components can be varied within a wide range in the oil-based suspension concentrates according to the invention. Thus, the concen-
trations

20    of agrocbemical active compounds are in general between 5 and 30 % by weight, preferably between I 0 and 25 % by weight,

of penetratioa promoter are in general between 5 and 55 % by weight, preferably between 15 and 40 % by weight,

25

of vegetable oil are in general between 15 and 55 % by weight, preferably between 20 and 50 % by weight,

of surfactants or dispersing aids are in general between 2.5 and 30 % by 30 weight, preferably between 5.0 and 25 % by weight and


of additives are in general between 0 and 25 % by weight, preferably between 0 and 20 % by weight.

The oil-based suspension concentrates according to the invention are prepared by mixing the components with one another in the ratios desired in each case. The

sequence  in which  the  constituents  are  blended  with  one  another  is  arbitrary.

Expediently, the solid components are employed in fmely ground state. However, it is also possible firstly to subject the suspension resulting after the blending of the constituents to a coarse grinding and then to a flne grinding so that the average

10    particle size is below 20 ~m. Suspension concentrates are preferred in which the solid particles have an average particle size of between 1 and 10 ~m.

The temperatures can be varied within a certain range when carrying out the process according to the invention. The process is in general carried out at temperatures

15    between lO'C and 60'C, preferably between 15'C and 40'C.

For carrying out  the  process  according  to  the  invention,  customary mixing  and

grinding equipment is suitable which is employed for the preparation of agrochemical formulations.
20

The oil-based suspension concentrates according to the invention are formulations which remain stable even after relatively long storage at elevated temperatures or in

the cold, since no crystal growth is observed. They can be converted into homo-geneous spray liquids by dilution with water. Th~uids are used accordin~
25    to customary methods, i.e., for example, by spraying, watering or injecting.

The application rate of the oil-based suspension concentrates according to the invention can be varied within a relatively wide range. It depends on the particular agrochemical active compounds and on their content in the formulations.


With the aid of the oil-based suspension concentrates according to the invention.

agrochemical active compounds can be applied to  plants and/or their habitat in a

particularly advantageous manner. The agrochemical active compounds contained in

this case display a better biological activity than on application in the form of the

corresponding conventional formulations.

The invention is illustrated by the following examples.


Preparation examples



For the preparation of a suspension concentrate

48.4  g  of thiacloprid

45.6  g  of a mixture of alkylarylsulphonate, ethylhexanol and alkanol ethoxylate

40.0    g  of pol)!Oxyethylene sorbitol oleate,

0.4    g  of silicone oil and

0.8  g  ofbutylhydroxytoluene

are added with stirring at room temperature to a mixture of

10    88.0 g of 2-ethyl-hexyl alknxylate of the formula

CH;-(CH ) --yH-CH,.-0-(EO);-(PO);-H
2 3
1    (lc-2)

20
 
c,H,

in which



-CH;-yH-0-
PO    represents    I    and
CH,

the numbers 5 and 3 are average values,

and
 

176.8 g of sunflower oil.

After addition is complete, the mixture is stirred at room tempemture for a further 10

minutes.  The  homogeneous  suspension  resulting  in  the  course  of  this  is  firstly

subjected to a coarse grinding and then to a fine  grinding so that a suspension is

obtained in which 90% of the solid particles have a particle size of below 6 ~m.



For the preparation of a suspension concentrate

78.2    g    of thiacloprid
40.0    g    of a mixture of calcium alkylarylsulphonate, alkylphenol ethoxylate and
        naphtha solution
40.0    g    of polyoxyethylene sorbitol oleate
0.4    g  of silicone oil and
0.8    g    of butylhydroxytoluene

10

are added with stirring at room temperature to a mixture of

80.0 g of2-ethyl-hexyl alkoxylate of the formula (lc-2) and 160.6 g of sunflower oil.

After addition is complete, the mixture is stirred at room tempemture for a further 10

15    minutes. The homogeneous suspension resulting in the course of this is firstly subjected to a coarse grinding and then to a fme grinding so that a suspension is obtained in which 90% of the solid particles have a particle size of below 6 ~m.
For the preparation of a suspension concentrate

50.4    g  of thiacloprid

27.5    g  of a mixture of alkylarylsulphonate and ethylhexanol
 

5.25    g of singly branched alkanol ethoxylate having on average 15 ethylene oxide groups

25.0    g  of polyoxyethylene sorbitol oleate

0.25    g  of silicone oil and

0.5    g  of butylhydroxytoluene

are added with stirring at room temperature to a mixture of

50.0    of 2-ethyl-hexyl alkoxylate of the formula (lc-2) and

91.1    g    of sunflower oil.

After addition is complete, the mixture is stirred at room temperature for a further 10

minutes.  The  homogeneous  suspension  resulting  in  the  course  of  this  is  firstly

subjected to a coarse grinding and then to a fme grinding so that a suspension is

obtained in which 90% of the solid particles have a particle size of below 6 Jlm.

10    Example4

For the preparation of a suspension concentrate

49.4    g  ofthiacloprid

23.75    g  of a mixture of alkylarylsulphonate and ethylhexanol

4.5    g of singly branched alkanol ethoxylate having on average 15 ethylene oxide groups

25.0    g  of polyoxyethyleue sorbitol oleate

0.25    g  ofsilicone oil and

0.5    g  of butylhydroxytoluene

!5    are added with stirring at room temperature to a mixture of

50.0 g of 2-ethyl-hexyl alkoxylate of the formula (lc-2) and 96.6 g of sunflower oil.

After addition is complete, the mixture is stirred at room temperature for a further 10

minutes.  The  homogeneous  suspension  resulting  in  the  course  of  this  is  firstly

subjected to a coarse grinding and then to a fme grinding so that a suspension is

obtained in which 90% of the solids particles have a particle size of below 6 ~m.



For the preparation of a suspensi~n concentrate

10

692.54    g  of thiacloprid

300.0    g  of  a  mixture  of  alkylarylsulphonate,  alkanol  ethoxylate  and  naphtha

solution

300.0  g  of polyoxyethylene sorbitol oleate

3,0  g  of silicone oil and

6.0  g  ofbutylhydroxytoluene

are added with stirring at room temperature to a mixture of

600.0  g    of2-ethyl-hexyl alkoxylate of the fOilllula (Ic-2) and

1098.46 g    of sunflower oil.

15    After addition is complete, the mixture is stirred at room temperature for a further 10 minutes. The homogeneous suspension resulting in the course of this is firstly subjected to a coarse grinding and then to a fme grinding so that a suspension is obtained in which 90% of the solid particles have a particle size of below 6 ~m.

20    Example6

For the preparation of a suspension concentrate

577.1    g of thiacloprid

327.5    g   of a mixture of alkylarylsulphonate, ethylhexaool aod alkanolethoxylate

250.0    g   of polyoxyethyleoe sorbitol oleate

2.5    g   of silicone oil aod

5.0    g   of butylhydroxytolueoe

are added with stirring at room temperature to a mixture of

500.0  g   of 2-ethyl-hexyl alkoxylate of the fonnula (lc-2) aod

837.9  g   of sunflower oil.

After addition is complete, the mixture is stirred at room temperature for a further 10

minutes.  The  homogeneous  suspension resulting  in  the  course  of  this  is  frrstly

subjected to a coarse grinding and then to a fine grinding so that a suspension is

obtaioed in which 90% of the solid particles have a particle size of below 6 11m.

For the preparation of a suspension concentrate

44.4  g   of thiacloprid

5.6    g   of 6-cyfluthrin

49.7    g    of a mixture of alkylarylsulphonate, ethylhexanol and alkaool ethoxylate

44.0    g    of polyoxyethyleoe sorbitol oleate

0.4    g    of silicone oil aod

0.8  g    of butylhydmxytolueoe

15    are added with stirring at room temperature to a mixture of

101.3    g    of2-ethyl-hexyl alkoxylate of the fonnula (lc-2) and

193.8    g    of sunflower oil.

After addition is complete. the mixture is stirred at room temperature for a further 10

minutes.  The  homogeneous  suspension  resulting  in  the  course  of  this  is  frrstly

subjected to a coarse grinding and then to a fme grinding so that a suspension is

obtained in which 90% of the solid panicles have a particle size of below 6 !liD.



For the preparation of a suspension concentrate

10

121.0    g  of thiacloprid

15.2    g  of B-cycluthrin

78.6    g of a mixtore of alkylarylsulphonate, ethylhexanol aod alkanol ethoxylate 60,0 g of polyoxyethylene sorbitol oleate

0,6  g  of silicone oil and

1.2    g  of butylhydroxytoluene

are added with stirring at room temperatore to a mixtore of

120.0  g   of 2-ethyl-hexyl alkoxylate of the formula (lc-2) and

203.4  g   of sunflower oil.

15    After addition is complete, the mixtore is stirred at room temperature for a further 10 minutes. The homogeneous suspension resulting in the course of this is frrstly subjected to a coarse grinding and then to a fme grinding so that a suspension is obtained in which 90% of the solid particles have a particle size of below 61-1m.



For the preparation of a suspension concentrate
138.5    g  ofthiacloprid,

60.0    g  of po1yoxyethylene sorbitol oleate

12.0    g  of polystyrene-acrylic acid copolymer

48.0  g  of polyoxyethylene fatty acid glyceride

0.6    g  of silicone oil and

1.2    g  ofbutylhydroxytoluene

are added with stirring at room temperatore to a mixture of

120.0  g    of alkanol alkoxylate of the formula



in whicb

    R    represents alkyl having 12 to 14 carbon atoms ,
10           
    EOrepresents -CHz-CHz-0 ,
            -CH;-<(H-0-
    PO    represents    I
            CH3
    and       
15    the numbers 3 and 6 are average values, and
219.7  g    ofrapeseedoil.   

After addition is complete, the mixture is stirred at room temperature for a further 10

minutes.  1he homogeneous  suspension resulting  in the  course of this  is  firstly

20    subjected to a coarse grinding and then to a fine grinding so that a suspension is obtained in whicb 90% of the solid particles have a particle size of below 6 1110.
 

Use Examples



Stability test

For the detennination of the stability, 100 gin each case of a suspension concentrate

of the composition described in Example 2 are stored for a number of weeks at

10

room temperature, +30°C,
+40°C

+54°C

15    alternating temperatures (6 hours at -lS"C, then 6 hours at +30°C).

The experimental results are compiled in the following tables.

Table Ia

20    Storage at -10°C

                    after   
                               
            2 weeks    4 weeks    8 weeks    16 weeks        26 weeks
    Sediment vol-ume in%                        99
                           
    Sediment                        none
                           
    Redispers-ability                        good
                           
    Particle size ""'Jinllm                        5.35
                           
    Content of active compound in%                        19.8
                               
    'l    Sediment volume = volume of the sediment phase in relation to    the total
        volume of the sample.                   
")    The average particle size which 90% of the solid particles in the oil phase
25        have was measured.                   
 
I!!!!tl!!

Stomge at room tempemture

                                        after       
                                               
                                2 weeks    4weeks    8 weeks    16 weeks    26 weeks
                                           
Sediment volwne in%            97        89
                                           
Sediment                none       
                                   
Redispers--ability            good        good
                                   
Particlesize    in1.1m            5.31        5.86
                                           
Content of active com-pound in %            20.1        19.6
                                               

*)    Sediment volume = volume of the sediment phase in relation to the total

volume of the sample.

'')    The average particle size which 90% of the solid particles in the oil phase

have was measured.

10    Table Ic Storage at +JO•c
                        after           
                               
                2 weeks    4weeks    8 weeks    16 weeks        26 weeks
                       
Sediment volume in %            94        84
                               
Sediment                    none            none
                           
Redispers-ability            good            good
                                   
Particle size        inp.m            6.57        5.74
                   
Content of active    com-pound in%            20.0        19.8
                               
')    Sediment volume = volume of the sediment phase in relation  to the  total

volume of the sample.

!5    '')    The average particle size which 90% of the solid particles in the oil phase

have was measured.
 



-27-

Tableld

Storage at -+40°C

                                            after       
                                                   
                                2 weeks    4 weeks    8 weeks    16 weeks    26 weeks
                                   
Sediment volume in %            93        92    87    82
                                           
Sediment                                   
                                   
Redispers-ability            good    good    good    good
                                           
Particle size        in!Jm            6.01        6.29    7.08    6.4
                               
Content of active com-pound in%            20.2        19.3    20.1    19.7
                                                   

*)    Sediment volume = volume of the sediment phase in relation to  the total

volume of the sample.

**)    The average particle size which 90% of the solid particles in the oil phase

have was measured.

Table le

Storage at +54°C

                    after           
                               
            2 weeks    4 - ks    8 weeks    16 weeks    26 weeks
                       
Sediment volume in%"')    96    89    83           
                           
Sediment                           
                       
Redispers-ability    good    good    good           
                           
Particle size    inJlm        8.81    6.61           
                       
Content of active com-pound in%    20.1    20.0    20.1           
                               

*)    Sediment volume = volume of the sediment phase in relation to  the total

volume of the sample.

**)    The average particle size which 90% of the solid particles in the oil phase

have was measured.

    Table If                       
10    Storage at alternating temperatures               
                           
                    after       
                           
            2~        8 weeks    16 weeks    26 weeks
                       
    Sediment volume in%        98    99       
                           
    Sediment            nooe           
                       
    Redispers-ability        good    good       
                           
    Particle size    in p.m        5.62    6.17       
                       
    Content of active com-pound in%        20.0    19.8       
                           

*) Sediment volume = volume of the sediment phase in relation to the total volwne of the sample.

**) The average particle size whicb 90% of the solid particles in the oil phase 15 have was measured.
 
Penetration test

In  this  test,  the  penetration  of active  compounds  through  enzymatically  isolated

cuticles of apple tree leaves was measured.

Leaves were used which were cut off in the fully developed state of apple trees of the

variety Golden Delicious. The cuticles were isolated by

!0

firstly filling, by means of vacuum infiltration with a pectinase solution (0.2 to 2% strength) buffered to a pH of between 3 and 4, leaf discs which had been marked on the bottom with dye and punched out,

15    then adding sodium azide and

allowing the leaf discs treated in this way to stand until the disintegration of the original leaf structure and the detachment of the non-cellular cuticles.

20    After this, only the leaf cuticles of the tops of the leaves which were free from stomata and hairs were used further. They were washed a number of times alternately with water and a buffer solution of pH 7. The clean cuticles obtained were fmaily mounted on small Teflon plates and smoothed out and dried using a gentle jet of air.

25    In the next step, the cuticle membranes thus obtained were placed into diffusion cells (=transport chambers) of stainless steel for membrane transport investigations. For this, using tweezers the cuticles were placed centrally on the edges of the diffusion celt. coated with silicone grease and sealed using a likewise greased ring. The arrangement had been chosen such that the morphological outer side of the cuticles
30    was directed outwards, i.e. to the air, while the original inner side was facing the

interior of the diffusion cell. The diffusion cells  were filled with water or with a

mixture of water and solvent.

For determination of the  penetration, 9 ~1 in each case of a spray liquor of the

composition mentioned below was applied to the outer side of a cuticle.

Spray liquor A

0.2 g   ofthiacloprid

10    0.4 g   of sunflower oil

0.4    g of formulating aids in 1 litre of water.

Spray liauor B

15

0.2 g  of thiacloprid

0.5 g   of 2-ethyl-hexyl alkoxylate of the formula (lc-2)

0.3    g of formulating aids in !litre of water.

20

Spray liquor C

0.2 g  ofthiacloprid

0.4 g  of sunflower oil

25    0.2 g of 2-ethyl-hexyl alkoxylate of the formula (Ic-2) 0.2 g of formulating aidx

in !litre of water.

Soray liquor D

0.2    g   of thiacloprid

0.3    g of formulating aids in llitre of water,

(prepared  from  commercially  available  suspension  concentrate  by  diluting  with

water).

CIPAC water was in each case used in the spmy liquors.

10

After the application of the spray liquors, the water was allowed to evaporate in each

case, then the chambers were in each case rumed and placed in thermostatted baths, a

saturated aqueous calcium nitrate 4-hydrate solution in each case being located under

the outer side of the cuticles. The penettation commencing therefore took place at a

15    relative humidity of 56% and a set temperature of 25'C. Samples were removed at regular intervals using a syringe and investigated by means of HPLC for the content of penetrated active compound.

The experimental results can be seen from the following table. The numbers stated

20    • are average values of 8 measurements.



    Active compound penetration in % after
           
    Sh    !Oh    20h
           
A    I    3    4
           
B    10    16    20
           
c    6    17    40
D            I


Use  of  oilMbased  suspension  concentrates #ri~~~![(e!l.:;t one  insec6Cide  from  the

neonicotinyl series for controlling eggs an~/rl}flphal stB~ t4A'flili(J~[)Jy means 'of spray

application

characterized in that the suspension concentrate c;J~i:1J''(nS

imidacloprid,

at least one penetrant selected flum the group of alkanolalkoxylates of f01mula (I),

R-0-( -AO)mR'    (l)

in which

10    R represents straightMchain or branched alkyl having 4 to 20 carbon atoms,

R' represents H, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl,

AO represents an ethylene oxide residue, a propylene oxide residue, a butylene

oxide residue or mixtures of ethylene oxide and propylene oxide residues or
IS    butylene oxide residues and

m represents numbers from 2 to 30,

at least one vegetable oil,

at least one non ionic surfactant or dispersant and/or at least one anionic surfactant or dispersant, and

20    if appropriate one or more additives from the gtoup of the emulsifiers, the an{ifoam agents, the preservatives, the antioxidants, the colourants and/or the inert fillers

    Usc according to Claim 1, chantcterized in that the suspension concentrate contains
    5 to 40% by weight of imidacloprid,
    5  to  55%  by  weight  of  at  !east  one  penetrant  selected  from  the  group  of
25    alkanolalkoxylates of fonnula (I),

in which

R represents straighHhain or branched alkyl having 4 to 20 carbon atoms,

R' represents H. methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-buty~ n-pentyl or n-hexyl,

AO represents an ethylene oxide residue, a propylene oxide residue, a buty!ene oxide residue or mixtures of ethylene oxide and propylene oxide residues or butylene oxide residues and

m represents numbers from 2 to 30,

10    IS to 55% by weight of at least one vegetable oil,

2..5 to 30% by weight of at least one nonionic surfactant or dispersnnt and/or at least one anionic surfactant or dispersant, and

if appropriate up to 25% by weight of one or more additives from the group of the emulsifiers, the antifoam agents, the preservatives, the antioxidants, the
15    colourants and/or the inert fillers.

3.    Method of controlling eggs and nymphal stages of whitefly, characterized in that an effective amount of at least one insecticide from the neonicotinyl series is applied to plants by spraying an oil-based suspension concentrate

chS!acterized in that the suspension concentrate contains

20    imidacloprid,

at least one penetrant selected from the group of alkanolalkoxylates of fOtmula (1),

R-0-(-AO)mR'    (I)

in which

R represents straight-chain or branched alkyl having 4 to 20 carbon atoms,
 

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