USOO607 1857A

United States Patent (19) 11 Patent Number: 6,071,857

Vogt et al. (45) Date of Patent: Jun. 6, 2000
54). PESTICIDAL COMPOSITIONS FOREIGN PATENT DOCUMENTS

75 Inventors: Manfred Vogt, Bad Säckingen, 299961 1/1989 European Pat. Off..
Germany; William Baettig, Pratteln, 2577533 1/1994 European Pat. Off..
Switzerland 3640267 6/1988 Germany.
90/4202 6/1990 Germany.
4239181 5/1994 Germany.
73 Assignee: Novartis Crop Protection, Inc., 92/6941 9/1992 South Africa.
Greensboro, N.C.
21 Appl. No.: 09/202,886 Primary Examiner José G. Dees
Assistant Examiner Alton Pryor
22 PCT Filed: Jun. 19, 1997 Attorney, Agent, or Firm William A. Teoli, Jr.; John D.
Peabody, III; Irving M. Fishman
86 PCT No.: PCT/EP97/03195
57 ABSTRACT
S371 Date: Dec. 22, 1998
A liquid pesticidal composition, which is Substantially free
S 102(e) Date: Dec. 22, 1998 of water, comprising a hydrophobic pesticide or mixture of
87 PCT Pub. No.: WO98/00009 pesticides dissolved in an organic Solvent and comprising as
Surfactants
PCT Pub. Date:Jan. 8, 1998 (1) a butanol-ethoxyate/propoxylate-blockcopolymer
30 Foreign Application Priority Data having 12-30 mol ethoxylate and 16-48 mol
propoxylate, in combination with
Jun. 28, 1996 DE Germany ........................... 968 10432
(2) a branched C-C alcohol ethoxylate having 5-10
51) Int. Cl." .............................. A01N3/02; AO1N 25/00 mol ethoxylate, and/or
52 U.S. Cl. ............................................. 504/116; 424/405 (3) a tristyrenephenol-ethoxylate having 8-30 mol
58 Field of Search .............................. 504/116; 424/405 ethoxylate, or its phosphate or Salt thereof.
56) References Cited The compositions include also gels having a Viscosity of 500
U.S. PATENT DOCUMENTS
to 20,000 mPas and comprising additionally a gelling agent.
4,870,103 9/1989 Roechling et al. ..................... 514/521
4,973,352 11/1990 Heinrich et al. ............................ 71/91 38 Claims, No Drawings
 6,071,857
1 2
PESTICIDAL COMPOSITIONS Preferred are Surfactants, wherein
(1) the butanol-ethoxylate/propoxylate-blockcopolymer
This appln is a 371 of PCT/EP97/03195 filed Jun. 19, has 20–24 mol, preferably 22 mol ethoxylate, and
1997. 30-36 mol, most preferably 34 mol propoxylate;
The present invention relates to Storage Stable, liquid, (2) the branched C-C alcohol ethoxylate is isotride
pesticidal compositions, the preparation of Such composi canol ethoxylate having 5-10 mol, most preferably 6-8
tions and a method of using Such compositions to combat mol ethoxylate; and
pests or as plant growth regulators. (3) the tristyrenephenol-ethoxylate has 16-18 mol
Alkylphenol ethoxylates, for example nonylphenol ethoxylate.
ethoxylates, and alkylbenzene Sulfonates and its Salts, for The composition of the invention is substantially free of
example dodecylbenzene Sulfonate calcium Salt, are com water, i.e. the amount of water is less that 0.5%. Some
monly used and well known Surfactants in water commercially available materials may contain a Small
emulsifiable pesticidal compositions. amount of water, which, when more than about 0.1% can be
Some of these Surfactants are not entirely Satisfactory; in removed for example in a separator.
particular with respect to their ecological and toxicological In another aspect of the invention the composition is a gel
properties. 15
with a viscosity of 500–20,000 mPas; preferably 800 to
There is still a need for further water-emulsifiable or 10,000 mPas and particularly 1000–5000 mPas.
water Soluble, liquid, homogeneous pesticidal compositions The Viscosity of the composition can be measured using
which are Storage Stable, ecological and toxicological for example a BROOKFIELD viscosimeter with spindles 1
favourable and which have good pesticidal efficacy. to 3 at 30 rpm.
Fatty alcohol ethoxylates, e.g. Co-Calcohol ethoxy In this case the composition additionally has to contain a
lates (EP-A-400,585) and tristyrenephenol-ethoxylates (EP gelling agent, for example oxypropylated cellulose, precipi
A-102,003) have been proposed, both in combination with tated or fused Silica (hydrophobi Zised or non
alkylbenzene Sulfonates, as Surfactants in water-emulsifiable hydrophobizised), gelatine, polysaccharides, tetramethyl
pesticidal compositions. C-C Alkyl ethoxylate/ decyne diol, ethoxylated dialkyl phenol, methylated clay,
propoxylate-blockcopolymers and tristyre nephenol 25 propylene carbonate, hydrogenated castor oil, ethoxylated
ethoxylates have been disclosed as Surfactants in aqueous vegetable oil, sodium benzoate and hexanediol. Preferred
suspensions (EP-A-261,492). gelling agent is oxypropylated cellulose.
A novel combination of Surfactants for water Gels are particularly Suitable for pesticides packing into
emulsifiable or water-Soluble pesticidal compositions has water Soluble bags or Sachets, which quickly dissolve when
now been found; the novel compositions are Storage Stable, put into the water.
easy to apply, ecological and toxicological favourable and The organic Solvents wherein the pesticide has to be
have good pesticidal efficacy. dissolved may be water-immiscible or water miscible or a
Accordingly, the present invention provides a water mixture thereof.
emulsifiable or water-Soluble, Storage Stable, liquid, pesti Suitable water-immiscible solvents in which the pesti
cidal composition, which is Substantially free of water, 35 cides may be dissolved are aliphatic and aromatic hydro
comprising a hydrophobic pesticide or mixture of pesticides carbons Such as hexane, cyclohexane, benzene, toluene,
dissolved in an organic Solvent and comprising as Surfac Xylene, mineral oil or kerosin, mixtures or Substituted
tantS
naphthalenes, mixtures of mono- and polyalkylated aromat
(1) a butanol-ethoxylate/propoxylate-blockcopolymer ics commercially available under the registered trademarks
having 12-30 mol ethoxylate and 16-48 mol 40 SOLVESSO and SHELLSOL and PETROL SPEZIAL,
propoxylate, in combination with halogenated hydrocarbons Such as methylene chloride, chlo
(2) a branched C-C alcohol ethoxylate having 5-10 roform and O-dichlorobenzene, phthalates, Such as dibutyl
mol ethoxylate, and/or phthalate or dioctyl phthalate; ethers and esters, Such as
(3) a tristyrenephenol-ethoxylate having 8-30 mol ethylene glycol monomethyl or monoethyl ether, fatty acid
ethoxylate, or its phosphate or Salt thereof. 45 esters, lactones Such as butyrolactone, ketones, Such as
Suitable Salts with bases are, for example, metal Salts, cyclohexanone; plant oils. Such as castor oil, Soybean oil,
Such as alkali metal or alkaline earth metal Salts, for example cottonseed oil and possible methyl esters thereof, as well as
Sodium, potassium calcium or magnesium Salts, or Salts with epoxidised coconut oil or soybean oil. Preferred water
ammonia or an organic amine, Such as morpholine, immiscible Solvents are aliphatic and aromatic
piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, 50 hydrocarbons, fatty acid esters (e.g. WITCONOL 2309),
for example ethyl-, diethyl-, triethyl- or dimethyl dipropyleneglycol monomethylether (e.g. DOWANOL
propylamine, or a mono-, di- or tri-hydroxy-lower DPM) and castor oil.
alkylamine, for example mono-, di- or tri-ethanolamine. Suitable water-miscible solvents in which the pesticides
The compositions also include gels having a Viscosity of may be dissolved are alcohols and glycols, Such as ethanol,
500 to 20,000 mPas and comprising additionally a gelling 55 ethylene glycol, Strongly polar Solvents, Such as N-methyl
agent. 2-pyrrollidone, tetramethylurea, gamma-butyrolacone,
The compositions according to the invention are Stable for dimethylsulfoxide, N,N-dimethylacetamid and dimethylfor
at least 12 months at 25 C. They are very well miscible with mamide; preferred are N-methyl-2-pyrrollidone and gamma
water, even at higher concentrations. butyrolacone.
The Surfactants can be combined, depending for example 60 Suitable pesticides are those which are substantially
on the kind of pesticide and the preferred Solvents, as insoluble in water (hydrophobic), but soluble in the organic
follows: Solvent.
(1) in combination with (2) and (3); (1) in combination The term pesticide is understood to encompass herbicides,
with (2); (1) in combination with (3). insecticides, acaricides, nematicides, ectoparasiticides, fun
The Surfactants mentioned above can be prepared by 65 gicides and plant growth regulators.
methods known per Se; they are also commercially avail With respect to their chemical constitution, these pesti
able. cides may belong to a very wide range of compound classes.
 6,071,857
3 4
Examples of compound classes to which the Suitable pesti insecticides, as Diazinon;
cide may belong are: acylalanines, haloacetanilides, triazole plant growth regulators, as TrineXapac-ethyl.
derivatives, phosphoric acid esters, pyrethroids, benzilic
acid esters, polycyclic halogenated hydrocarbons, diphenyl Suitable concentrations in relation to the composition are
ether derivate S, formamidine S, Strobilurine S, 5 (% weight per volume of the total composition; 1000 g per
aryloxyphenoxy-alkanoic acid derivatives. Examples of liter correspond to 100%)
suitable individual compounds of the above mentioned a) of the hydrophobic pesticide or mixture of pesticides:
compound classes are listed below. Where known, the 1 to 99%, preferably 10 to 90% and 20 to 50%;
common name is used to designate the individual com
pounds (q.v. the Pesticide Manual, 10th edition, 1994, b) of the organic solvent: 1 to 96%, preferably 10 to 80%
British Crop Protection Council). and 20 to 70%;
Haloacetanilides: Dimethachlor, Metolachlor,
Pretilachlor, 2-chloro-N-(1-methyl-2-methoxyethyl)-acet-2, c) of the surfactants: 3 to 80%, preferably 10 to 40% and
6-Xylidide, Alachlor, Butachlor, Propachlor, Dimethenamid. 20 to 30%; wherein of
Diphenyl ether derivates: Bifenox, 4-(4-Pentyn-1-yloxy) surfactant (1): 2 to 25%, preferably 5 to 20%,
diphenylether, Acifluorfen, Oxyfluorfen, Fluoroglycofen 15
surfactant (2): 2 to 40%, preferably 5 to 25%,
ethyl, Fomesafen, cis-trans-(+)2-ethyl-5-(4-phenoxy surfactant (3): 2 to 20%, preferably 5 to 15%;
phenoxymethyl)-1,3-dioxolane (“diofenolan').
Phenoxypropionic acid derivatives: Fluazifop-butyl, d) of the gelling agent: 0.1 to 10% preferably 0.5 to 5%.
Haloxy fop-methyl, Haloxy fop-(2-ethoxyethyl), It may be advantageous to add additionally an alkylben
Fluorotopic, Fenoxaprope thyl, Quizalofop -ethyl, Zene Sulfonate or its Salt, preferably dodecylbenzene Sul
Propaquizafop, Diclofop-methyl. fonate calcium salt in an amount of 1 to 10%, preferably 2
Acylalanines: Furalaxyl, Metalaxyl, R- Metalaxyl, Ben to 4% by weight in relation to the volume of the compo
Zoylprop ethyl, Benalaxyl, OXadixyl, Flamprop methyl. Sition.
Triazole derivatives: Difenoconazole, Etaconazol, It may be advantageous to combine the pesticide or
Propiconazole, Penconazole, Triadimefon, Epoxiconazole, 25
Tebuconazole, Bromuconazole, Fenbuconazole, Cyprocona mixture of pesticides with a Safener.
Zole. Another object of the invention is a proceSS for preparing
Phosphoric acid esters: Piperophos, Anilofos, Butamifos, a liquid pesticidal composition as herein described, by
AZamethiphos, ChlorfenVinphos, Dichlorvos, Diazinon, intimateley mixing, optionally by warming, until a homo
Methidathion, AZinphos ethyl, AZinphos methyl, geneous phase is achieved.
Chlorpyrifos, Chlorthiofos, Crotoxyphos, Cyanophos, In another aspect of the invention the composition is an
Demeton, Dialifos, Dimethoate, Disulfoton, Etrimfos, aqueous spray mixture.
Famphur, Flusulfothion, Fluthion, Fonofos, Formothion, Before the application, the composition of the invention
Heptenophos, lSofen phos, Isoxathion, Malathion, may be diluted with water by Simple mixing at ambient
Mephospholan, Mevinphos, Naled, Oxydemeton methyl, 35 temperature in order to get a ready for use Spray mixture.
Oxyde profos, Parathion, Phoxim, Pyrimiphos methyl, This spray mixture may be an aqueous emulsion or a
Profenofos, Propaphos, Propetamphos, Prothiophos, Solution or a Suspension, depending on the kind of compo
Quinallphos, Sulprofos, Phemephos, Terbufos, Triazophos, Sition.
Trichloronate, Fenamipos, IsaZophos, S-benzyl-O,O-
diisopropylphosphorothioate, Edinphos, PyraZophos. 40 The resulting Spray mixtures are stable, i.e. they remain as
Pyrethroids: Allethrin, Bioallethrin, Bioresmethrin, a homogeneously emulsified phase, as a Solution or as a
Cyhalotrin, Cyper me thrin, C. - Cyper me thrin, homogeneously distributed Suspension on Standing without
(p-Cypermethrin, Deltamethrin, Fenpropathrin, Fenvalerate, agitation for at least one hour to 12 hours or even more.
S-Fenvalerate, Flucythrinate, Fluvalinate, Permethrin, Preferred concentrations of the spray mixture are 0.1 to 5
Pyrethrine, Resmethrin, Tetramethrin, Tralomethrin, 45 %, more preferred 0.5 to 2% pesticide in relation to the spray
Ethophenprox, Cyfluthrin, Cycloprothrin, Tefluthrin, mixture.
Flufenprox, Silafluofen, Bifenthrin, Fenfluthrin, Bromfen Further aspects of the invention include a method of
proX. preventing or combatting infestation of plants or animals by
BenZilic acid esters: Brompropylate, Chlorbenzylate, pests and regulating plant growth by diluting the composi
Chlorpropylate. 50 tion with water and applying a pesticidally effective amount
Polycyclic haloaenated hydrocarbons: Aldrin, Endosul to the plant, animal or locus as desired.
fan.
Strobilurines: Kresoxim-methyl, Azoxystrobin (BAS
490F), Methoxyimino-2-1-(3-trifluoromethyl-phenyl)-
ethylideneaminooxymethyl-phenyl)-acetic acid methyl 55 PREPARATION EXAMPLES
eSter.
Miscellaneous: Tridemorph, Bromoxynil, Carboxin,
Prochlora Z, Propargite, Dicamba, Fen piclonil, The following Examples illustrate the invention in more
Fenpropimorph, Fenpropidin, Fludioxonil, Pymetrozine, detail. The registered trademarks and other designations
Pyrifenox, Pyriproxyfen, Trinexapac-ethyl, Fluazinam. 60 denote the following products:
Preferred pesticides are
herbicides, as Propaquizafop, Piperophos and Propanil;
fungicides, as Methoxyimino-2-1-(3-trifluoromethyl
phenyl)- ethylideneaminooxymethyl-phenyl)-acetic (1) WITCONOLNS 500 K (R) (WITCO) Copolymer of butanol-34
PO/22 EO,
acid methyl ester, Propiconazole, Cyproconazole, 65 (2) GENAPOL X-080 (R) (HOECHST) Isotridecanol-8 EO
Fluazinam, Metalaxyl or R-Metalaxyl (enantiomer of GENAPOL X-060 (R) (HOECHST) Isotridecanol-6 EO
Metalaxyl), or a mixture thereof;
 6,071,857
S 6
-continued -continued
(3) SPROPHOR BSU (R) (RHONE-P) Tristyrenephenole-16 EO % component type
SOPROPHOR 3D33 (R) (RHONE-P) Tristyrenephenol-poly-EO
phosphate 5 9.3 SOPROPHORBSU (R) surfactant (3)
2.3 SOPROPHOR3D33 (R) surfactant (3)
WITCONOL 2309 (R) Fatty acid methylester 64.6 1-Methyl-2-pyrrolidone solvent
EMULSOGENEL (E) castor oil-36 EO
SPEZIAL 200 (R) Mixture of aromatic hydrocarbons Density: 1.07 g/cm
KLUCELM (R) Oxypropylated cellulose (gelling agent)
DOWANOL DPM (E) Dipropyleneglcyol monomethylether (mixture of 1O
isomers)
EO = ethyleneoxid Example 5
PO = propyleneoxid
% in weight per volume of the total composition (i.e. 1000
g per liter correspond to 100%). The components are inti- 15 % component type
mateley mixed, optionally by warming, until a homoge 11.8 Methoxvimino-2-1-(3-trifluoromethwl-phenwl)- fungicide
neous phase is achieved. y {2-1-( yl-phenyl)
ethylidene-aminooxymethyl-phenyl-acetic acid
methyl ester
Example 1 12.5 Propiconazole fungicide
2 11.4 WITCONOLNS 500 K (R) surfactant (1)
11.4 SOPROPHORBSU (R) surfactant (3)
52.9 1-Methyl-2-pyrrolidone solvent
% component type Density: 1.095 g/cm
1.O.O Propaquizafop herbicide
5.0 WITCONOLNS SOOK (R) surfactant (1) 25
35.O GENAPOL X-06O (R) surfactant (2) Example 6
1.O.O 1-Methyl-2-pyrrolidone solvent
40.O PETROLSPEZAL 200 solvent

Density: 1.02 g/cm

3O % component type
19.0 Methoxyimino-2-1-(3-trifluoromethyl-phenyl)- fungicide
Example 2 ethylidene-aminooxymethyl-phenyl-acetic acid
methyl ester
12.5 Propiconazole fungicide
13.O WITCONOLNS SOOK (R) surfactant (1)
% component type 35 10.0 SOPROPHOR BSU (R) surfactant (3)
3.O SOPROPHOR3D33 (R) surfactant (3)
14.5 Piperophos herbicide 42.5 1-Methyl-2-pyrrolidone solvent
25.0 Propanil herbicide
8.0 WITCONOLNS SOOK (R) surfactant (1) Density: 1.1 g/cm
12.O GENAPOL X-06O (R) surfactant (2)
40.5 Dipropyleneglycol monomethyl ether solvent 40
Density: 1.065 g/cm Example 7

Example 3
45 % component type
23.3 Cyproconazole fungicide
1O.O WITCONOLNS SOOK (R) surfactant (1)
% component type 1O.O SOPROPHOR3D33 (R) surfactant (3)
17.4 Methoxyimino-2-1-(3-trifluoromethyl-phenyl)- fungicide 23.O 1-Methyl-2-pyrrolidone solvent
i?lan a-ami - a rafir ari
ethylidene-aminooxymethyl-phenyl-acetic acid 50 33.7 SOLVESSO 200 solvent
methyl ester + . 3
12.3 Propiconazole fungicide Density: 1.073 g/cm
11.7 WITCONOLNS SOOK (R) surfactant (1)
11.7 SOPROPHORBSU (R) surfactant (3)
46.9 1-Methyl-2-pyrrolidone solvent Example 8
55
Density: 1.11 g/cm

Example 4 % component type

60 12.5 Methoxyimino-2-1-(3-trifluoromethyl-phenyl)- fungicide
ethylidene-aminooxymethyl-phenyl-acetic acid
methyl ester
% component type 12.5 WTCONOLNS SOOK (R) surfactant (1)
1O.O SOPROPHORBSU (R) surfactant (3)
12.1 Methoxyimino-2-1-(3-trifluoromethyl-phenyl)- fungicide 2.5 SOPROPHOR3D33 (R) surfactant (3)
ethylidene-aminooxymethyl-phenyl-acetic acid 62.5 1-Methyl-2-pyrrolidone solvent
methyl ester 65
11.7 WITCONOLNS SOOK (R) surfactant (1) Density: 1.07 g/cm
 6,071,857
7 8
Example 9
-continued
% component type
% component t
ype 5 16.0 PETROLSPEZIAL 200 (R) solvent
18.5 Methoxyimino-2-1-(3-trifluoromethyl-phenyl)- fungicide 25.3 Gamma-Butyrolactone solvent
ethylidene-aminooxymethyl-phenyl-acetic acid
methyl ester Density: 1.184 g/cm
8.0 Cyproconazole fungicide
1O.O WITCONOLNS SOOK surfactant (1)
S.O GENAPOL X-080 (R) surfactant (2) 10 Example 14
S.O SOPROPHORBSU (R) surfactant (3)
53.5 1-Methyl-2-pyrrolidone solvent

Density: 1.09 g/cm % component type

15 59.6 Diazinon insecticide
Example 10 8.0 WITCONOLNS SOOK (R) surfactant (1)
8.0 SOPROPHORBSU (R) surfactant (3)
24.4 SOLVESSO 150 solvent

% component Density: 1.073 g/cm

type 2O
15.0 Methoxyimino-2-1-(3-trifluoromethyl-phenyl)- fungicid
ngicide Example 15
ethylidene-aminooxymethyl-phenyl-acetic acid
methyl ester
7.0 R-Metalaxyl fungicide
12.5 WITCONOLNS SOOK surfactant (1)
12.5 SOPROPHORBSU (R) surfactant (3) 25 % component type
53.0 1-Methyl-2-pyrrolidone solvent
26 Trinexapac-ethyl plant growth regulator
Density: 1.081 g/cm 21.0 WITCONOLNS SOOK surfactant (1)
7.0 GENAPOL X-06O (R) surfactant (2)
O.8 KLUCELM(R) gelling agent
Example 11 3O 45.2 DOWANOLDPM(R) solvent

Density: 1.027 g/cm; Viscosity; ca. 2700 m Pas (Spindle 3/30 rpm)

% component type Example 16

12.5 Methoxyimino-2-1-(3-trifluoromethyl-phenyl)- fungicide 35
ethylidene-aminooxymethyl-phenyl-acetic acid
methyl ester
7.5 R-Metalaxyl fungicide % component type
3.O WITCONOLNS SOOK surfactant (1)
3.O GENAPOL X-080 (R) surfactant (2) 26.3 Trinexapac-ethyl plant growth regulator
45.5 1-Methyl-2-pyrrolidone solvent 40 21.4 WITCONOLNS SOOK surfactant (1)
27.5. Aromatic solvent 230 solvent 7.1 GENAPOL X-06O (R) surfactant (2)
45.2 WITCONOL 2309 (R) solvent
Density: 1.081 g/cm
Density: 0.98 g/cm
Example 12 * All the compositions according to the examples are stable
for at least 12 months at 25 C.
After diluting with water the compositions form an emul
% component type Sion or, depending O the pesticide, solvent and
9.3 R-Metalaxyl fungicide 50
concentration, a clear Solution. Both the emulsions and
4.0 WITCONOLNS SOOK surfactant (2)
(1) Solutions are stable without agitation for at least one to 12
16.O GENAPOL X-080 (R) surfactant hours or even more.
5.0 Gamma-Butyrolactone solvent What is claimed is:
27.0 Fatty acid methyl ester Me C 6-10 solvent 1. A liquid pesticidal composition comprising a hydro
Density: 1.035 g/cm 55 phobic pesticide or mixture of pesticides dissolved in an
organic Solvent together with Surfactants, which composi
tion is Substantially free of water and comprising as Said
Example 13 Surfactants
(1) a butanol-ethoxylate/propoxylate blockcopolymer
60 having 12-30 mol ethoxylate and 16-48 mol
propoxylate, in combination with
% component type (2) a branched C-C alcohol ethoxylate having 5-10
17.7 R-Metalaxyl fungicide mol ethoxylate, and/or
age S. WCONo. NS SOOK E. (1) (3) a tristyrenephenol-ethoxylate having 8-30 mol
50 GENAPOL X-06O (R) surfactant (2) 65 ethoxylate, or its phosphate or Salt thereof;
5.0 SOPROPHORBSU (R) surfactant (3) wherein Said organic Solvent is water-immiscible and
Selected from the group consisting of aliphatic and aromatic
 6,071,857
9 10
hydrocarbons, phthalates, ethers and esters, fatty acid esters, 20. A composition according to claim 1, wherein the
lactones, ketones, castor oil, Soybean oil, cottonseed oil and concentration of the Surfactants (1), (2) and/or (3) is 3 to
possible methyl esters thereof, and epoxidised coconut or 80% by weight in relation to the volume of the composition.
Soybean oil or wherein Said organic Solvent is water miscible 21. A composition according to claim 20, wherein the
and Selected from the group consisting of alcohols, glycols concentration of the surfactants is 10 to 40% by weight in
N-methyl-2-pyrrollidone, tetramethylurea, gamma relation to the Volume of the composition.
butyrolactone, dimethylsuloxide N,N-dimethylacetamid, 22. A proceSS for preparing a liquid pesticidal composi
tion according to claim 1 by intimately mixing, optionally by
and dimethylformamide; warming, Said pesticide, Said organic Solvent, and Said
whereby a Storage Stable composition is obtained. Surfactants until a homogeneous phase is obtained.
2. A composition according to claim 1, wherein the 23. An acqueous microemulsion or Solution prepared by
butanol-ethoxylate/propoxylate-blockcopolymer (1) has mixing the composition according to claim 1 with water.
20–24 mol ethoxylate, and 30-36 mol propoxylate. 24. A method of preventing or combatting infestation of
3. A composition according to claim 1, wherein the plants or animals by pests by diluting the composition
branched C-C alcohol ethoxylate (2) is isotridecanol according to claim 1 with water and applying a pesticidally
ethoxylate having 5-10 mol ethoxylate. 15 effective amount to the plant, animal or locus.
4. A composition according to claim 1, wherein the 25. The composition of claim 2 wherein said butanol
tristyrenephenol-ethoxylate (3) has 16-18 mol ethoxylate. ethoxylate/propoxylate-blockcopolymer (1) has 22 mol
5. A composition according to claim 1 having a Viscosity ethoxylate and 34 mol propoxylate.
of 800 to 10,000 mPas. 26. The composition of claim 3 wherein the branched
6. A composition according to claim 5, wherein the C-C alcoholethoxylate is isotridecanol ethoxylate having
gelling agent is Selected from the group consisting of 6-8 mol ethoxylate.
oxypropylated cellulose, precipitated or fused Silica 27. The composition of claim 5 having a viscosity of
gelatine, polysaccharides, tetramethyl decyne diol, ethoxy 1000-5000 mPas.
lated dialkyl phenol, methylated clay, propylene carbonate, 28. The composition of claim 12 wherein said pesticide is
hydrogenated castor oil, ethoxylated vegetable oil, Sodium a herbicide and is Selected from the group consisting of
benzoate and hexanediol. 25 Propaquizafop, Piperaphos, and Propanil.
7. A composition according to claim 6, wherein the 29. The composition of claim 13 wherein said pesticide is
gelling agent is oxypropylated cellulose. a fungicide and is Selected from the group consisting of
8. A composition according to claim 1, wherein the methoxy imino - {2-- (-trifluoromethyl-phenyl)-
Surfactants are ethylideneaminooxymethyl-phenyl acetic acid methyl
(1) a butanol-ethoxylate/propoxylate-blockcopolymer ester, Propiconazole, Cyproconazole, fluaZinam, Metalaxyl
having 12-30 mol ethoxylate and 16-48 mol or R-Metalaxyl, and mixtures thereof.
propoxylate, in combination with 30. The composition of claim 14 wherein said pesticide is
Diazinon.
(2) a branched C-C alcohol ethoxylate having 5-10 31. The composition of claim 15 wherein said pesticide is
mol ethoxylate. TrineXapac-ethyl.
9. A composition according to claim 1, wherein the 35
32. The composition of claim 17 wherein said pesticide is
Surfactants are present in said composition at a concentration of 20 to 50%
(1) a butanol-ethoxylate/propoxylate-blockcopolymer in relation to the Volume of the composition.
having 12-30 mol ethoxylate and 16-48 mol 33. The composition of claim 19 wherein said organic
propoxylate, in combination with Solvent is present in Said composition at a concentration of
(3) a tristyrenephenol-ethoxylate having 8-30 mol 40 20 to 70% in relation to the volume of the composition.
ethoxylate, or its phosphate or Salt thereof. 34. The composition of claim 21 wherein said surfactants
10. A composition according to claim 1, wherein the are present in Said composition at a concentration of 20 to
organic Solvent is Selected from aliphatic and aromatic 30% in relation to the volume of the composition.
hydrocarbons, fatty acid esters, dipropyleneglycol monom 35. The method of claim 24 which further regulates plant
ethylether and castor oil. 45 growth wherein Said pesticide is a plant growth regulator
11. A composition according to claim 1, wherein the and Said composition is applied to Said plant or locus.
organic Solvent is N-methyl-2-pyrrollidone or gamma 36. Aliquid pesticidal composition, which is Substantially
butyrolacone or a mixture thereof. free of water, comprising a hydrophobic pesticide or mixture
12. A composition according to claim 1, wherein the of pesticides dissolved in an organic Solvent and comprising
pesticide is a herbicide. 50
as Surfactants
13. A composition according to claim 1, wherein the (1) a butanol-ethoxylate/propoxylate blockcopolymer
pesticide is a fungicide. having 12-30 mol ethoxylate and 16-48 mol
14. A composition according to claim 1, wherein the propoxylate, in combination with
pesticide is an insecticide. (2) a branched C-C alcohol ethoxylate having 5-10
15. A composition according to claim 1, wherein the 55 mol ethoxylate, and/or
pesticide is a plant growth regulator. (3) a tristyrenephenol-ethoxylate having 8-30 mol
16. A composition according to claim 1, wherein the ethoxylate, or its phosphate or Salt thereof;
concentration of the pesticide or mixture of pesticides is 1 to Said composition further comprising a gelling agent, and
99% by weight in relation to the volume of the composition. wherein Said composition is in the form of a gel and has a
17. A composition according to claim 16, wherein the 60 viscosity of 500 to 20,000 mPas.
concentration of the pesticide or mixture of pesticides is 10 37. A composition according to claim 36, wherein the
to 90% in relation to the volume of the composition. concentration of the gelling agent is 0.1 to 10% by weight
18. A composition according to claim 1, wherein the in relation to the Volume of the composition.
concentration of the organic solvent is 1 to 96% by weight 38. The composition of claim 37 wherein said gelling
in relation to the Volume of the composition. agent is present in Said composition at a concentration of 0.5
19. A composition according to claim 18, wherein the 65
to 5% in relation to the volume of the composition.
concentration of the organic solvent is 10 to 80% by weight
in relation to the Volume of the composition. k k k k k
 UNITED STATES PATENT AND TRADEMARK OFFICE
CERTIFICATE OF CORRECTION
PATENT NO. : 6,071,857 Page 1 of 1
DATED : June 6, 2000
INVENTOR(S) : Vogt et al.

It is certified that error appears in the above-identified patent and that said Letters Patent is
hereby corrected as shown below:

Title page, item 30,

Line 1, should read: "Jun. 28, 1996 EP Europe......................9681 0432.3'
Claims, column 10
Insert the following:
"39. A liquid pesticidal composition, which is substantially free of water, comprising a
hydrophobic pesticide or mixture of pesticides dissolved in an organic solvent and
comprising as surfactants
(1) a butanol-ethoxylate/propoxylate blockcopolymer having 12-30 mol
ethoxylate and 16-48 mol propoxylate, in combination with
(2) a branched C-C1s alcohol ethoxylate having 5-10 mol ethoxylate, and/or
(3) a tristyrenephenol-ethoxylate having 8-30 mol ethoxylate, or its phosphate
or salt thereof; wherein said organic solvent is water miscible and selected from the
group consisting of alcohols, glycols, N-methyl-2-pyrrolidone, tetramethylurea, gamma
butyrolactone, dimethylsulfoxide, N,N-dimethylacetamid, and dimethylformamide."

Signed and Sealed this

Twenty-fifth Day of September, 2001
Attest:

7.A.4 fl &ée.
NICHOLAS P. GODICI
Attesting Officer Acting Director of the United States Patent and Trademark Office