NZ623850B2 - Agricultural formulations with aromatic solvents and acyl morpholines - Google Patents
Agricultural formulations with aromatic solvents and acyl morpholines Download PDFInfo
- Publication number
- NZ623850B2 NZ623850B2 NZ623850A NZ62385012A NZ623850B2 NZ 623850 B2 NZ623850 B2 NZ 623850B2 NZ 623850 A NZ623850 A NZ 623850A NZ 62385012 A NZ62385012 A NZ 62385012A NZ 623850 B2 NZ623850 B2 NZ 623850B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- formulation
- morpholine
- acyl
- formula
- polar aprotic
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 114
- -1 acyl morpholines Chemical class 0.000 title claims abstract description 50
- 239000003849 aromatic solvent Substances 0.000 title description 3
- 238000009472 formulation Methods 0.000 claims abstract description 59
- 239000004480 active ingredient Substances 0.000 claims abstract description 35
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 28
- 229940113083 morpholine Drugs 0.000 claims abstract description 26
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract description 19
- RUOJZAUFBMNUDX-UHFFFAOYSA-N Propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000000839 emulsion Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 18
- 239000003995 emulsifying agent Substances 0.000 claims description 16
- 239000005839 Tebuconazole Substances 0.000 claims description 9
- PXMNMQRDXWABCY-UHFFFAOYSA-N Tebuconazole Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 claims description 6
- 150000001409 amidines Chemical class 0.000 claims description 6
- 150000001556 benzimidazoles Chemical class 0.000 claims description 6
- 235000010233 benzoic acid Nutrition 0.000 claims description 6
- 150000001559 benzoic acids Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000004659 dithiocarbamates Chemical class 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 241001182492 Nes Species 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 150000003918 triazines Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-M carbamodithioate Chemical compound NC([S-])=S DKVNPHBNOWQYFE-UHFFFAOYSA-M 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 230000000240 adjuvant Effects 0.000 claims 1
- 238000000518 rheometry Methods 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 abstract description 11
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- 150000002500 ions Chemical class 0.000 description 10
- 239000000575 pesticide Substances 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-Ethylhexanol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- 239000005906 Imidacloprid Substances 0.000 description 4
- YWTYJOPNNQFBPC-UHFFFAOYSA-N Imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- 229940056881 imidacloprid Drugs 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ZBJVLWIYKOAYQH-UHFFFAOYSA-N naphthalen-2-yl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=C(C=CC=C2)C2=C1 ZBJVLWIYKOAYQH-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 description 3
- DLEWDCPFCNLJEY-UHFFFAOYSA-N 1-morpholin-4-ylpropan-1-one Chemical compound CCC(=O)N1CCOCC1 DLEWDCPFCNLJEY-UHFFFAOYSA-N 0.000 description 3
- QHTQREMOGMZHJV-UHFFFAOYSA-N Benthiocarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
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- 238000001556 precipitation Methods 0.000 description 2
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- RLLPVAHGXHCWKJ-HKUYNNGSSA-N (3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-HKUYNNGSSA-N 0.000 description 1
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- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 description 1
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- ORFPWVRKFLOQHK-UHFFFAOYSA-N 4-amino-N-tert-butyl-5-oxo-3-propan-2-yl-1,2,4-triazole-1-carboxamide Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 description 1
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- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- VQOIVBPFDDLTSX-UHFFFAOYSA-M sodium;3-dodecylbenzenesulfonate Chemical class [Na+].CCCCCCCCCCCCC1=CC=CC(S([O-])(=O)=O)=C1 VQOIVBPFDDLTSX-UHFFFAOYSA-M 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);N-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N κ-bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
Abstract
The disclosure relates to a formulation comprising at least one agriculturally active ingredient; at least one aromatic hydrocarbon; and at least one acyl morpholine according to the formula (I), where R is H, CH3 or C2H. The formulation may further provide a polar aprotic solvent. The acyl morpholine may be N-formyl morpholine and a polar aprotic solvent may be propylene carbonate. The disclosure also relates to a method for treating a plant or seed using said formulation. ne may be N-formyl morpholine and a polar aprotic solvent may be propylene carbonate. The disclosure also relates to a method for treating a plant or seed using said formulation.
Description
AGRICULTURAL FORMULATIONS WITH AROMATIC SOLVENTS AND ACYL
MORPHOLINES
Field of Invention
The present invention relates in general to a solvent system sing an aromatic
hydrocarbon and an acyl morpholine as a t for agriculturally active ients.
The invention also relates to a ation comprising an agriculturally active ingredient
and such a t system.
Background of the ion
Agriculturally active ingredients, such as pesticides and plant growth regulators, have
conventionally been provided to the end-user in different concentrated forms to be
diluted in water or other suitable medium to form a dilute ready-to-use formulation by
the end—user. Such concentrated forms include solid formulations, e.g. s, and
liquid formulations. in many applications, liquid formulations are preferred as problems
of dusting of toxic powders and slow dissolution in the diluent may be avoided.
An emulsion concentrate typically comprises an agricultural active ingredient, a water-
insoluble solvent, and an emulsifier, and when added to the water, it spontaneously, or
after active mixing, e.g. stirring, forms an oil-in-water emuision, the agricultural active
primarily being present in the emulsion droplets. This type of concentrated formulation
is especially le for agricultural active ingredients that are water insoluble/have low
water solubility, and where the recommended concentration in the ready-to-use
formulation exceeds the solubility of the agricultural active ingredient.
It is important that the active ient is stably dissolved in the emulsion trate.
Precipitation of the agriculturall active ingredient may result in a loss of efficacy. Should
the active ingredient be concentrated to the precipitates, it is prevented from being
evenly distributed when sprayed on a field.
There is thus a need in the field to find new and improved solvents/solvent s for
agriculturally active ingredients, which can be used in agricultural formulations,
especially in form of emulsion concentrates.
Summary of the Invention
One object of the present invention is to meet the needs in the art and to provide a
solvent that can be used in ltural formulations.
Another object of the invention is to provide a solvent for agricultural actives that allows
for a concentrated formulation of solvent and ltural active, in which the
agriculturally active ingredient have a reduced tendency to form precipitates.
Another object of the invention is to provide a solvent for agricultural active ingredients
that allows for a trated formulation of solvent and agricultural active to be mixed
with an aqueous medium without or with only minor precipitation of the active
ingredient.
The ing objects should be read disjunctively with the object of at least providing
the public with a useful choice.
The present inventors have now surprisingly found that certain combinations
comprising aromatic arbons and acyl morpholines are suitable as t
systems for agriculturally active ingredients. These combinations have been especially
useful in emulsfiable concentrated formulations.
In one aspect, there is provided a formulation comprising:
a) at least one agriculturally active ingredient selected from the group
consisting of triazoles, strobiiurins, nebis(dithiocarbamate) compounds,
benzimidazoles, .phenoxy carboxylic acids, benzoic acids, sulfonylureas, nes,
pyridine carboxylic acids, neonicotinides, amidines, organophosphates, pyrethroids and
mixtures thereof;
b) at least one aromatic hydrocarbon; and
c) at least one acyl morpholine according to the formula (I),
° /—"\
N 0
R \_/
[followed by page 2a]
where R is H, CH3 or CgH5.
In a further , there is provided a use of a solvent system comprising
(i)an aromatic hydrocarbon;
(ii)an acyl morpholine according to the formula (I),
N O
R \_/
where R is H, CH3 or C2H5,
(iii) optionally a polar aprotic solvent different from an acyl morpholine of formula (I),
(iv) optionally additional components;
as a solvent for an lturally active ingredient selected from the group consisting of
triazoles, strobilurins, alkylenebis(dithiocarbamate) compounds, benzimidazoles,
phenoxy carboxylic acids, benzoic acids, sulfonylureas, triazines, pyridine carboxylic
acids, neonicotinides, amidines, organophosphates, roids and mixtures thereof.
In a further aspect, there is provided a ation sing
a) a tebuconazole
b) an aromatic hydrocarbon, and
c) N-formyl morpholine.
In a first aspect, the present ion relates to a formulation comprising a) at least
one agriculturally active ingredient, b) at least one aromatic hydrocarbon c) at least one
acyl morpholine of formula (I),
N O
R \__/
where R is H, CH3 or CZH5,
[followed by page 2b]
d) optionally at least one polar aprotic solvent different from an acyl morpholine of
formula (I), and
e) optionally additional component(s).
The formulation may be a fully or ially anhydrous formulation or may be an
aqueous formulation, such as an emulsion.
In a second aspect, the present invention relates to a method for treating a plant, by
contacting said plant with a ation of the invention.
followed b a e 3
In a third aspect, the present invention relates to the use of a solvent system
comprising aromatic solvent and an acyl morpholine of formula (I) and optionally a
polar aprotic solvent, as a solvent for an agricultural active.
These and further aspects will now be described further.
Detailed Description of the invention
The agriculturally active ingredients contemplated for use in the present invention, also
referred to in the art as agricultural actives, are preferably selected from the group
consisting of pesticides and plant growth regulators.
The agriculturally active ingredients are preferably selected amongst those having low
water solubility, and most preferably amongst those being water insoluble.
The term “agriculturally active ingredient” as used herein is to be taken as
encompassing any organic compound being agriculturally . However, to the
extent that the aromatic arbon, the acyl morpholines of the formula (I) or the
polar aprotic co-solvents as defined herein, are agriculturally active, these are not
ered as agriculturally active ients.
The term und having low water solubility” as defined herein, relates to a
compound having a lity of at most 5, such as at most 1 g/l, for example at most
0.7 gll in water.
In the t of the present invention, water solubility is ed according to ASTM
E 1148-87 “Standard Test Method for Measurements of Aqueous Solubility”.
As used herein, the term “pesticide” refers to a compound that will prevent, destroy,
repel, or mitigate any pest.
As used herein, the term "plant growth regulator" refers to a compound, which through
logical action will accelerate or retard the rate of growth or rate of maturation or
ise alter the behaviour of ntal or crop plants or the products thereof.
Pesticides and plant growth regulators especially contemplated for use in the present
invention are organic compounds, preferably synthetic organic compounds.
Pesticides contemplated for use in the present invention e, fungicides,
herbicides, insecticides, miticides, nematicides, acaricides, and molluscicides.
PCT/EPZO12/073372
Preferred agriculturally active ingredients contemplated for use in the present invention
include pesticides and plant growth regulators of the classes triazoles, strobilurins,
alkylenebis(dithiocarbamate) nds, benzimidazoles, phenoxy carboxylic acids,
benzoic acids, sulfonylureas, nes, pyridine carboxylic acids, neonicotinides,
amidines, organophosphates, and pyrethroids.
Examples of fungicides contemplated for use in the present invention includefungicides
of the classes triazoles (e.g. tebuconazole, tetraconazole, cyproconazole,
onazole, difenconazole, propiconazole, prothioconazole), strobilurins (e.g.
trifloxystrobin, azoxystrobin, fluoxastrobin, pyraclostrobin),
alkylenebis(dithiocarbamate) compounds (e.g. mancozeb) and benzimidazoles (e.g
dazim).
Examples of herbicides contemplated for use in the present invention includephenoxy
carboxylic acids (e.g. 2,4—D-acid, MCPA), benzoic acids (e.g. Dicamba-acid),
sulfonylureas (e.g. methylsulfuron-methyl, rimsulfuron), triazines (e.g. atrazine and
simazine), triazolinones (e.g. amicarbazone) and pyridine carboxylic acids (e.g.
triclopyr).
Examples of insecticides contemplated for use in the present ion include
neonicotinides (e.g. thiamethoxam, clothianidin, thiacloprid, dinotefuran, iprid,
nitenpyram, imidacloprid), amidines (e.g. amitraz), organophosphates (e.g.
chlorpyrifos) and pyrethroids (e.g. permethrin, bifenthrin, deltamethrin).
For a detailed description of each of the mentioned pesticides and plant growth
regulators, nce is made to handbooks, 9.9. “The e—Pesticide Manual v4.0” from
BCPC Publications Ltd, Alton, Hampshire. (ISBN 1 901396 42 8).
The aromatic hydrocarbon may be any ic hydrocarbon or a e of aromatic
hydrocarbons le for use in ltural formulations.
Examples of such aromatic hydrocarbons include, toluene, xylene and other alkylated
benzenes, such as trimethyl e, methyl ethyl benzene, n-propyl benzene,
isopropyl benzene, methyl isopropyl e, methyl n—propyl benzene,
diethylbenzene, tetramethylbenzene, and mixtures of two or more thereof, optionally
with additional components. Industrial aromatic hydrocarbons, such as Solvesso 100,
Solvesso 150, Solvesso 150 ND, Solvesso 200 and so 200 ND available from
ExxonMobil, Shellsol X7B, Shellsol A100, Shellsol A150 and Shellsol A15OND,
available from Shell Chemicals, and Farbasol, available from Orlen Oil, are also
contemplated as the aromatic hydrocarbon for use in the t ion.
The aromatic hydrocarbon typically has an initial boiling point (IBP) in the range of from
100 to 270°C, ably in the range of 150 to 250°C, and a dry point (DP) of from 100
to 320°C, preferably in the range of from 170 to 310°C. in the context of the present
invention, the values of initial boiling point and the dry point are as obtained by the
method according to ASTM D86.
The aromatic hydrocarbon typicaiiy has a mixed aniline point of below 25°C, such as in
the range of from 5, for example from 9, to 20, for e to 16°C, as measured
according to the method of ASTM D611.
The aromatic hydrocarbon typically has a kinematic viscosity at 25°C of from 0.6 to 3.7
meIs, preferably from 0.9 to 3.6 mmzls. in the context of the present invention, the
values of kinematic viscosity are as obtained at 25°C by the method of ASTM D445.
In one ment, the aromatic hydrocarbon is a mixture having an initial boiling point
in the range of from 160 to 170° and a dry point in the range of from 175 to 185°C, and
preferably a viscosity of from 0.88 to 0.98 mm2/s.
In another embodiment, the aromatic arbon is a mixture having an initial boiling
point in the range of from 176 to 186° and a dry point in the range of from 202 to
212°C, and preferably a viscosity of from 1.18 to 1.28 mm2/s.
in another embodiment, the aromatic hydrocarbon is a mixture having an initial boiling
point in the range of from 174 to 184° and a dry point in the range of from 189 to
199°C, and ably a viscosity of from 1.11 to 1.21 mm2/s.
In another embodiment, the aromatic hydrocarbon is a mixture having an l boiling
point in the range of from 222 to 232° and a dry point in the range of from 282 to
292°C, and preferably a viscosity of from 2.98 to 3.08 mm2/s.
in another embodiment, the aromatic hydrocarbon is a mixture having an initial boiling
point in the range of from 237 to 247° and a dry point in the range of from 294 to
304°C, and preferably a ity of from 3.49 to 3.59 mmZ/s.
The acyl morpholines contemplated for use in a ation of the present invention
include 4—formyl morpholine (R = H, also referred to as N-formyl morpholine or NFM),
4-acetyl morpholine (R = CH3, also referred to as N—acetyl morpholine or NAM), 4-
propionyl morpholine (R = Csz, also ed to as N-propionyl morpholine or NPM)
and mixtures thereof, preferably 4-formyl morpholine. Preferably, 4-formyl line
represents at least 50, most preferably at least 90, such as 100 wt% of the acyl
morpholines of formula (l) present in the formulation. r, for formulations
comprising the pesticide N,N’-bis-[(1-formamid0-2,2,2—trichloro)ethyl]piperazine, it is
preferred that the acyl morpholine is selected from 4-acetyl morpholine and 4—propionyl
morpholine.
The acyl morpholines as such are well known nds and are commercially
available from rd chemical suppliers.
Polar aprotic solvents, which are different from an acyl morpholine of formula (l), herein
referred to as “polar aprotic solvents”, may be included in formulations of the present
invention.
The polar aprotic solvent is ably selected from those polar aprotic ts having
a flash point of at least 65°C, as measured according to ASTM D93.
The polar aprotic solvent is preferably selected from the group consisting of a sulfoxide,
an amide, a hydrocarbyl— or hydrocarbylene carbonate, and mixtures thereof. Preferred
sulfoxides include dimethyl sulfoxide. Preferred hydrocarbyl carbonates include di—alkyl
ates, such as those with (31—08 alkyl chains. Preferred hydrocarbylene-
carbonates include alkylene carbonates, more preferably 02—04-alkylenecarbonates,
most preferably propylene carbonate. More preferably, the polar aprotic co-solvent is
ed from the group consisting of dimethyl sulfoxide, propylene carbonate and
mixtures thereof, most ably propylene carbonate.
One or more additional components may be present in a formulation of the invention.
Examples of such additional components include one or more nts, such as
bioefficacy enhancers that increase the bioefficacy of agricultural actives, humectants,
wetting , rheology modifiers, surfactants, emulsifiers, stickers, drift reducers
and/or other additional components conventionally used in agricultural compositions.
Water is not contemplated for use as a member of the above "additional components”.
A formulation of the present invention may be a fully or essentially anhydrous
ation, such as comprising less than 10, preferably less than 1 wt% of water, or
may be an aqueous formulation, such as an emulsion, typically an oil-in-water
on, y comprising at least 90, such as at least 99 wt% water, based on the
total weight of the formulation of the invention.
The concentration of the at least one agriculturally active ingredient in a formulation of
the present invention is suitably within the solubility range of the specific compound in
the specific solvent system.
The concentration of the agriculturally active ingredient in a formulation of the present
invention is usually from about 0.1, such as from about 10, for example from about 20,
to about 950, such as to about 500, for example to about 300 g/l based on the total
volume of an anhydrous formulation of a formulation of the invention.
In ations of the present ion, the concentration of the at least one
agriculturally active ingredient may be from 50 to 250 g/l.
The concentration of the aromatic hydrocarbon in a ation of the present invention
is usually from 25, such as from 50, for example from 100, to 900, such as to 700, for
e to 500 g/l based on the total volume of an anhydrous formulation of the
ion.
When a polar c solvent is present, the weight ratio between acyl morpholine of
formula (I) and polar aprotic solvent is usually from 5:95, from 30:70, from 50:50, from
70:30, or from 75:25, to 95:5, to 90:10, or to 85:15. For example, the weight ratio
n acyl morpholine of formula (I) and polar aprotic solvent may be about 80:20.
A formulation of the present invention may comprise from about 10, such as from 50, or
from 100, to about 600, such as to about 400, or to about 250 g/l of the total of c) acyl
line of the formula (l) and, if present, d) polar c co—solvent, based on the
total volume of an anhydrous formulation of the invention.
If present, the tration of additional components in a formulation of the present
invention is usually from 10, such as from 20, or from 50, to 250, such as to 150, or to
100 g/l based on the total volume of an anhydrous formulation of the invention.
The formulations according to the invention may be prepared in such a manner that the
components are mixed with one another in the desired ratios and to the desired
concentrations. in general, the formulations are prepared at a temperature of between
and 50°C. Apparatuses that are employed for the preparation of agricultural
formulations can also be employed as apparatuses for the preparation of the
formulations of the present invention.
The composition of the present invention may be an emulsiflable concentrated
composition, hereinafter and in the art commonly ed to as an “emulsifiable
W0 2013f076202
concentrate", or “EC”, comprising a formulation as defined herein, including an
emulsifying agent. Hence, such an emulsifiable concentrate comprises an lturally
active ingredient, an aromatic hydrocarbon, an acyl morphoiine of the formula (I),
optionally a polar aprotic co-solvent, and an emulsifier.
The concentration of agriculturally active ingredient is usually too high for end-use, and
the emulsifiable concentrate is intended to be diluted with an aqueous medium into a
work-composition.
The emulsifiable concentrate preferably comprises water in an amount below the
amount at which an oil-in-water emulsion is formed. Preferably, the emulsifiable
concentrate comprises less than about 10, more preferably less than about 1 wt% of
water, based on the total weight of the emulsifiable concentrate. Most preferably, the
emulsifiable trate of the present invention is essentially free from water in the
sense that the emulsifiable concentrate does not contain water beyond what is
inevitable from the equilibrium with the surrounding atmosphere.
Emulsifiers plated for use in the present invention e surfactants known as
emulsifying agents by those skilled in the art, e.g. c tants, non-ionic
surfactants, polymers, and blends thereof, especially blends comprising anionic and
non-ionic surfactants.
Examples of non—ionic surfactants contemplated for use as emulsifying agents in the
present invention include, but are not limited to lated, preferably ethoxylated
and/or propoxylated alcohols, preferably containing from 8 to 22 carbon atoms;
alkyl(poly)glycosides, such as straight or branched 04-010 alkyl(poly)glycosides;
alkoxylated, preferably ethoxyiated, sorbitan or sorbitol esters; castor oil lates;
and tristyrylphenol lates. red ethoxylated alcohols have a degree of
ethoxylation of from 1 to 50, more preferably 2 to 20, most preferably 3 to 10.
Examples of lated alcohols contemplated for use in the present invention include
those based on branched alcohols, such as the Guerbet alcohols, e.g. 2-
propylheptanol and 2-ethylhexanol, and Cm— or C13—OXO-alcohols, i.e. an alcohol
e whose main component is formed by at least one branched C10— or Chg-alcohol,
and the alcohols commercially available as Exxal alcohols from Exxon Mobile
Chemicals and Neodol alcohols from Shell Chemicals.
Examples of anionic surfactants contemplated for use as emulsifying agents in the
t invention include uccinates, alkylbenzene sulfonic acid salts, such as
calcium or sodium dodecylbenzene sulfonate, alkyl sulphonates, alkyl ether sulphates,
phosphate esters of optionally alkoxylated, preferably ethoxylated andlor propoxylated,
alcohols, xylene or cumene sulfonate salts, and naphthalene or alkylnaphthalene
sulfonates, which may be condensated, and mixtures thereof
Examples of polymers for use alone or in combination as emulsifying agent include
ethylene oxide-propylene oxide block co-polymers, acrylic acid based comb polymers,
xanthan gum and mixtures thereof.
in an emulsifiable concentrate of the present invention, the concentration of emulsifier
is usually from 10, such as from 50, to 200 such as to 150 g/l based on the total volume
of an ous formulation of the ion.
The present invention also relates to an aqueous, oil—in-water, emulsion comprising an
aqueous medium, at least one agriculturaliy active ingredient, preferably having low
water solubility, an aromatic hydrocarbon, an acyl morpholine according to the formula
(i), an fier and, optionally, a polar aprotic solvent and/or additional components.
For example, such an emulsion may be obtained by mixing an s medium and
an emulsifiable concentrate as previously defined herein or by separately mixing the
components.
As used herein, the term ion” shall be interpreted to include macro emulsions,
nano ons, micro emulsions and suspo-emulsions, i.e. emulsions in which a
particulate solid is suspended.
The aqueous medium that is a component of the emulsion of the t invention
usually comprises water as the major component. Preferably, water constitutes at least
50 wt% such as at least 75 wt%, for example at least 90 wt% of the aqueous medium.
The aqueous medium may further comprise other components, eg. salts buffering
agents, trolling agents, such as acids or bases, fertilizers, etc.
When the emulsifiable concentrate is mixed with the aqueous medium, an emulsion is
formed, the emulsion y being the work composition that will be used by the end—
user, with the advantage that the er does not have to handle and store large
quantities of work composition, but can e the amounts necessary for the
moment.
ons of the present ion may be prepared by mixing an emulsifiable
concentrate of the invention with an aqueous medium at a volume ratio between the
2012/073372
emulsifiable concentrate and aqueous medium of from about 1:25, preferably from
about 1:50, more preferably from about 1:100; to about 1:1000, preferably to about
1:500, more preferably to about 1:300. In a representative emulsion of the present
invention, the volume ratio fiable concentratezaqueous medium is about 1:200.
An age of the present invention is that the agriculturally active ingredient exhibit
a low, or no, tendency to precipitate or crystallise when the formulation is in
concentrated form, i.e. comprising less than 10 wt% water, preferably less than 1 wt%
water
r advantage of the t invention is that even at high dilutions in the
1O emulsion, i.e. at low ratios between the formulations and the aqueous medium, the
tendency of the agriculturally active ingredient to precipitate or crystallise is low, also at
temperatures icantly below room temperature, such as at 5°C. This is
advantageous for many reasons. Should it be necessary for the end-user to stop
spraying before having consumed a full batch of emulsion, the unused on will be
possible to use later, for example the next day, even if the unused emulsion was stored
at reduced temperatures.
In a further aspect, the present invention provides a method for treating a plant or seed,
wherein the plant or seed is contacted with a formulation of the invention. The desired
amount of agriculturally active ingredient to be contacted with a plant or seed by means
of such method depends on several parameters, such as the biological activity of the
agriculturally active, but generally, the amount is adjusted to be ient for the
agriculturally active ingredient to perform its desired activity.
As used herein, “plant” includes all parts of a plant, including roots, stems, leaves,
flowers and fruits.
in one embodiment of the treatment method, the plant or seed is contacted with a
formulation of the present invention, y an oil—in—water emulsion, by means of
spraying.
In another embodiment of the treatment method, a plant or a seed, usually a seed, is
ted with a formulation of the invention by dipping or soaking the plant or seed in
the formulation.
Exgeriments
To obtain the formulations disclosed in table 1 below, agriculturally active ingredient
(Al), emulsifier, aromatic hydrocarbon and a mixture of N—formyl—morpholine (N FM) and
propylene carbonate (PC) (80:20 wtrwt) was mixed together to the required amounts
with a ic stirrer until the active ingredient dissolved in the formulation.
The finished formulations were put into a refrigerator for seven days at 0°C. All
ations were judged by the naked eye if it contained any crystals after the g.
The results are shown in Table 1.
Table 1
Aromatic
NFM PCi C t I
Formul. Al Emulsrflers- - * H drocarbonV rys a 5
(80:20) formed
(Added to 1 I)
1** 1009/] [Dog/I3%th3/’:asn N35021: Solvesso 150
+ g ponto —
. . Yes
lopnd
2 LQ + 30 gll Sponto AP 540 g/l N0
Imidacloprid
40 Q!"
8% 3:393:04 + 20 Solvesso 200
3** Emamectin — Yes
Benzoate l
40 g/l l
8/0! a“ 8?;(32904 + 20 Solvesso 200
4 Emamectin 200 g/l I No
Benzoate g ero
- X lene
** 'j’ggfif’e“ y
150 g/l Sponto AP202 - Yes
' Xylene
6 fi’g’ggj‘f’e“ 150 g/I Sponto AP 202 50 9/! No
2,4-D-lBE
SO'VeSSO 100
7“ 200g/l 45 gll Sponto 500T +
_ Yes
Thiobencarb 15 g/l Sponto 300T
400 g/I
2009/1 45 Q“ Sponto 500T + Solvesso 100
8 50 g/| NO
ncarb 15 9“ Sponto 300T
400 g/I
2 4-D-IBE
’ 30 gll Sponto 500T +
274g/l Solvesso 100
9“ 30 g/l Sponto 300T
_ Yes
Thiobencarb
647g/l
2 4-D—IBE
’ 30 g/l Sponto 500T +
274g/l Solvesso 100
30 g/l Sponto 300T 30 g/l No
Thiobencarb
647g/l
250 g/l
quizalofop_p_ 4O g/i Berol 9968 + so 150
11“ Yes
ethyl 40 g/l Berol 9969
250 g/I
quizalofop-p- 40 g/I Berol 9968 + 40 S0 V9550| 150
12 1009“ N°
ethyl g/l Berol 9969
* Emulsifiers available from Akzo Nobel Surface Chemistry AB, Stenungsund, Sweden
** Comparative example
From the results, it is evident that the ion of acyl morpholine and polar c
solvent in the aromatic hydrocarbon reduces the formation of crystals.
Example 2
To obtain formulations disclosed in table 2, agriculturally active ingredient was added to
measuring flask along with the N—formyl morpholine (NFM), propylene carbonate (PC)
and emulsifier to the required amounts. Aromatic hydrocarbon, Solvesso 150 ND was
then added so that the whole mixture amounted to 1|. The mixture was stirred with a
magnetic stirrer until the active dissolved in the formulation. Finished formulations were
put into a erator for seven days at 0°C.
All formulations were judged by the naked eye if it contained any crystals after the
storing. The results are shown in table 2.
WO 76202
Table 2
Emulsifiers Solvesso
F°""“'- A' Crystals
(9/1) 150 ND formed
13M 2509/! Quizalafop-
80(A) Up to 1 | Yes
p_ ethyl
14 2509/I Quizalafop— 80 (A) Up to 1 | No
p_ ethyl
2509/! Quizalafop- 80 (A) Up to 1 | No
p— ethyl
16 2509/I Quiza!afop- 80 (A) No
p— ethy!
17 2509/I Quizalafop-
80(B) No
p- ethyl
_)__._
18 2509/I Quuzalafop- 80(s) No
p- ethy!
19 2509i! Quizalafop-
80(B) NO
p- ethyl
Tebuconazole
21 2509fl
Tebuconazole
22 2509”
Tebuconazole
23 2509A
Tebuconazole
24”, 2509/!
Tebuconazole
r ** 1009/!
Yes
Imidacloprid
26 1009/!
Imidacloprid
27 1009" 80(3) 448 112 Up to 1 | No
lmidacloprid
A— 50 wt% 2-ethyl hexanol alkoxylated with 35 moles propylene oxide and 32 moles
ethylene oxide per mole alcohol (2EH+35PO+32EO), 20 wt% Calcium dodecyl bensen
sulfonate and 20wt% n-butanol
B- 50 wt% 2-ethyl l alkoxylated with 35 moles propylene oxide and 32 moles
ethylene oxide per mole alcohol (2EH+35PO+32EO), 20 wt% Calcium dodecyl bensen
sulfonate and 20wt% Solvesso 150ND
** Comparative example
From the results, it is evident that the inclusion of acyl morpholine and polar aprotic
solvent in the aromatic hydrocarbon reduces the formation of crystals.
Example 3 - Emulsion on
Formulations containing 250 g/l of Tebuconazole were formulated together with 100 g/I
of surfactant blend (36 wt% l hexanol ethoxylate ylate, 13 PO/ZOEO, 30
wt% calcium dodecyl bensen sulfonate, 14 wt% HD ocenol (60/65) ethoxylate, 23 E0
and 20 wt% n-butanol) and diluted as follows:
1) yl morfoline : propylene carbonate (in the weight ratio 4:1) up to 1 liter
2) N-formyl morfoline : propylene carbonate (in the weight ratio 4:1) 2009/l and up
to 1 liter with so 150ND
Each formulation was emulsified into water (342 ppm CaCog—eq) at ambient
temperature (~22°C) in the volume ratio (formulation:water) 5 ml:95 ml dilution. The
emulsions were poured into 100 ml glass test tubes and ted for stability by
measuring the volume of cream/oil/sedimentation visible in the test tubes after 2 hours.
The appearance was judged by ocular inspection with the naked eye and the s
can be seen in table 3
Table 3
Formulation I Appearance after 2 hrs
28** ‘ 2 ml of ntationicrystals
No cream or sedimentation
** Comparative Experiment
Claims (19)
1. A formulation sing: a) at least one agriculturaiiy active ingredient selected from the group consisting of ies, strobiiurins, aikylenebis(dithiocarbamate) 5 compounds, benzimidazoles, phenoxy carboxylic acids, benzoic acids, sulfonylureas, nes, pyridine carboxyiic acids, neonicotinides, amidines, organophosphates, pyrethroids and mixtures thereof; b) at ieast one aromatic hydrocarbon; and c) at least one acyl line according to the formula (I), O I‘“—\ N 0 10 R \_/ where R is H, CH3 or CZH5.
2. A formulation ing to claim 1, wherein said aromatic hydrocarbon has an initial boiling point (lBP) of from 100 to 270°C.
3. A formulation according to any one of the ing claims, further comprising 15 d) at least one polar aprotic solvent different from an acyl morpholine of formula (I).
4. A formulation according to claim 3, wherein said polar aprotic solvent ent from an acyl morpholine of formula (1) is selected from the group consisting of a sulfoxide, an amide, a hydrocarbyl carbonate, a hydrocarbyiene carbonate and 2O mixtures thereof.
5. A formulation according to claim 4, wherein said polar aprotic solvent different from an acyl morpholine of formula (l) is selected from the group consisting of a dimethyl sulfoxide, propylene carbonate, and mixtures thereof.
6. A formulation according to any one of claims 3 to 5, comprising an acyl 25 morpholine which is N-formyi morpholine and a polar aprotic t which is propylene carbonate.
7. A formulation according to any one of claims 3 to 6, wherein the weight ratio between acyl morpholine according to the formula (I) and polar aprotic solvent different from an acyl morpholine of formula (I) is from 70:30 to 90:10.
8. A formulation according to any one of the preceding claims, further comprising e) at least one additional component selected from the group consisting of adjuvants, surfactants, emulsifiers, wetting agents, rheology ers and mixtures f.
9. A formulation ing to any one of the preceding claims, sing: from 10 to 800 g/l of a); 10 from 50 to 900 g/l of b); from 10 to 600 g/l of the total of c) and if present d); and from 0 to 250 g/l of e); based on the total volume of an anhydrous formulation.
10. A formulation according to any one of the preceding claims comprising from 10 15 to 200 g/l of emulsifier, based on the total volume of an anhydrous formulation.
11. A ation according to any one of the preceding claims comprising at most 10 wt% water based on the total weight of the formulation.
12. A formulation according to any one of the claims 1 to 10, comprising at least 90 wt% water based on the total weight of the formulation. 20
13. A formulation according to claim 12 in the form of an -water emulsion.
14. A method for treating a plant or seed, comprising contacting said plant or seed with a formulation according to any one of the claims 1 to 13.
15. The use of a solvent system comprising (i)an aromatic hydrocarbon; 25 (ii)an acyl morpholine according to the formula (I), N O R L/ where R is H, CH3 or 0%, (iii) optionally a polar aprotic solvent different from an acyl morpholine of formula (l), and (iv) optionally additional components; as a solvent for an lturally active ingredient selected from the group consisting of triazoles, strobilurins, alkylenebis(dithiocarbamate) compounds, benzimidazoles, phenoxy carboxylic acids, benzoic acids, sulfonylureas, triazines, pyridine ylic acids, neonicotinides, amidines, organophosphates, pyrethroids and mixtures thereof.
. A formulation comprising a tebuconazole an aromatic arbon, and 1O yl morpholine.
. A formulation according to any one of claims 1 to 13 or 16, substantially as herein described with reference to any one of the Examples thereof.
18. A method according to claim 14, substantially as herein described with reference to any one of the Examples thereof. 15
19. The use according to claim 15, substantially as herein described with reference to any one of the es thereof.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11190509.7 | 2011-11-24 | ||
EP11190509 | 2011-11-24 | ||
US201161564002P | 2011-11-28 | 2011-11-28 | |
US61/564,002 | 2011-11-28 | ||
PCT/EP2012/073372 WO2013076202A1 (en) | 2011-11-24 | 2012-11-22 | Agricultural formulations with aromatic solvents and acyl morpholines |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ623850A NZ623850A (en) | 2016-04-29 |
NZ623850B2 true NZ623850B2 (en) | 2016-08-02 |
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ID=
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