OA16306A - Formulations. - Google Patents
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- OA16306A OA16306A OA1201300031 OA16306A OA 16306 A OA16306 A OA 16306A OA 1201300031 OA1201300031 OA 1201300031 OA 16306 A OA16306 A OA 16306A
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- formulation
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- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 13
- 238000009472 formulation Methods 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
- -1 2-hydroxy-l-methylethyl Chemical group 0.000 claims description 8
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 claims description 5
- 239000005730 Azoxystrobin Substances 0.000 claims description 5
- WFDXOXNFNRHQEC-GHRIWEEISA-N Azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 claims description 5
- 239000005799 Isopyrazam Substances 0.000 claims description 5
- 102000019259 Succinate Dehydrogenase Human genes 0.000 claims description 4
- 108010012901 Succinate Dehydrogenase Proteins 0.000 claims description 4
- 239000003905 agrochemical Substances 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- SCYRDAWUOAHQIE-UHFFFAOYSA-N 2-hydroxypropyl benzoate Chemical compound CC(O)COC(=O)C1=CC=CC=C1 SCYRDAWUOAHQIE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005760 Difenoconazole Substances 0.000 claims description 2
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims description 2
- CWSLAZMJENUWPG-UHFFFAOYSA-N 1-hydroxybutan-2-yl benzoate Chemical compound CCC(CO)OC(=O)C1=CC=CC=C1 CWSLAZMJENUWPG-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 23
- JATXLCWZFQHYGQ-UHFFFAOYSA-N benzoic acid;propane-1,2-diol Chemical compound CC(O)CO.OC(=O)C1=CC=CC=C1 JATXLCWZFQHYGQ-UHFFFAOYSA-N 0.000 description 7
- 239000000575 pesticide Substances 0.000 description 7
- 239000005747 Chlorothalonil Substances 0.000 description 4
- 239000005758 Cyprodinil Substances 0.000 description 4
- CRQQGFGUEAVUIL-UHFFFAOYSA-N Chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 3
- 238000003972 agrochemical formulation Methods 0.000 description 3
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AIAYSXFWIUNXRC-PHIMTYICSA-N (1R,5S)-3-[hydroxy-[2-(2-methoxyethoxymethyl)-6-(trifluoromethyl)pyridin-3-yl]methylidene]bicyclo[3.2.1]octane-2,4-dione Chemical compound COCCOCC1=NC(C(F)(F)F)=CC=C1C(O)=C1C(=O)[C@@H](C2)CC[C@@H]2C1=O AIAYSXFWIUNXRC-PHIMTYICSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N Phenylpropanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N Triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 229960002622 Triacetin Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 2
- 229940007550 benzyl acetate Drugs 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 239000001087 glyceryl triacetate Substances 0.000 description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- LBPLLQWWWCNJBE-UHFFFAOYSA-N 1-hydroxypropan-2-yl benzoate Chemical compound OCC(C)OC(=O)C1=CC=CC=C1 LBPLLQWWWCNJBE-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 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
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-Butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- QDBFCZCIBRFQBR-UHFFFAOYSA-N 4-hydroxybutyl benzoate Chemical compound OCCCCOC(=O)C1=CC=CC=C1 QDBFCZCIBRFQBR-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- AKGGYBADQZYZPD-UHFFFAOYSA-N Benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 241000238578 Daphnia Species 0.000 description 1
- 206010062080 Pigmentation disease Diseases 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- KGEKLUUHTZCSIP-UMNHJUIQSA-N [(1S,3R,4R)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-UMNHJUIQSA-N 0.000 description 1
- 230000000895 acaricidal Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 231100000584 environmental toxicity Toxicity 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000002363 herbicidal Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 230000000749 insecticidal Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Abstract
This invention relates to a formulation comprising a compound of formula (I) where R1 is hydrogen, methyl, ethyl, propyl or butyl; R2 is methyl or ethyl; R3 is hydrogen, methyl or ethyl; and n is 1, 2 or 3; to the use of a compound of formula (I) as a solvent; and to certain novel compounds of formula (I).
Description
FORMULATIONS
This invention relates to the use of certain alkylene glycol benzoate compounds as solvents, especially in formulations, particularly in agrochemical formulations and in cnvironmcntally fricndly formulations; and to certain novel compounds. The solvents of the présent invention are found to be particularly effective when solubilising pesticides of the families strobilurins, triazoles and succinate dehydrogenase inhibitors (SDIII) (particularly pyrazoles; suitably pyrazam chemistry).
Nowadays, the Formulation Chemist is required to address a number of environmental critcria when developing new formulations. Ideally, a suitable solvent will display many or ail of the following properties: an excellent dissolving power for pesticides or other organic molécules; made from plant or animal renewable resources; low skin irritation; low ecotoxicity, for example to daphnia; low volatile organic content; and a high flash point. The compounds of the présent invention each display ail or many of these properties, in particular an excellent dissolving power; the compounds may be used effectivcly as solvents.
Accordingly, the présent invention provides a formulation comprising a compound of formula (I)
R3 (I where R1 is hydrogen, methyl, ethyl, propyl or butyl; R2 is methyl or ethyl; R3 is hydrogen, methyl or ethyl; and n is 1, 2 or 3.
Propyl and butyl groups are straight or branched chains. Examples are «o-propyl, n-propyl, n-butyl, sec-butyl and tert-butyl.
Suitably R1 is H.
Suitably R2 is methyl.
Suitably R3 is H.
Suitably n is 1.
Suitably the invention provides the use of a compound of formula (1) in an agrochemical formulation.
The compounds of the présent invention may be used as solvents.
Many of the compounds disclosed by the présent invention are novel.
-2Therefore in a further aspect, the présent invention provides a compound of formula (I) as defined above; provided that the compound is not 2-hydroxypropyl benzoate,
2-hydroxy-1 -methylethyl benzoate, l ,2 butanediol-2-benzoate, l,2 butancdiol-l-benzoate or l-propanol-2(2-hydroxypropoxy)-l-benzoate.
Table l provides structures and certain spectroscopic data for suitable compounds of formula (I):
Table 1
| Compound Number | R' | R2 | R1 | n | MH lfom GCMS | IR band cm'1 OH | IR band cm'1 ester | IR band cm’1 aromatic |
| 1 | H | CHj | H | 1 | 181 | 3340 | 1712 | 1600 |
| 2 | H | CH2CH3 | H | 1 | 195 | 3355 | 1715 | 1600 |
The compounds of the présent invention are easy to prépare; for instance, a glycol ether îs rcactcd with an aromatic compound with a suitable leaving group, for example benzoyl chloride.
The compounds of the invention may bc used in a variety of end use applications (including agrochemical formulations), particularly as solvents. These solvents may be used with a wide variety of materials, including herbicides, fongicides, acaricides, nematicides and insecticides [and also plant growth rcgulators].
The présent invention encompasses all isomers, or mixtures of isomers, of compounds of formula (I) and also encompasses mixtures of two or more different compounds of formula (I).
The compounds of the invention may bc used to formulate solutions of a variety of materials, including agrochemicals, which may be formulated as émulsion or dispersion concentrâtes, émulsions in water or oil, microcncapsulated formulations, aérosol sprays or fogging formulations; and these may be forther formulated into granular materials or powders, for example for dry application or as water-dispersîblc formulations. The solutions so formed may also bc used directly on soil or plants or in other non-agrochemical applications.
Examples of such applications include paper makîng, water treatment, forestry applications, public health treatments, use in municipal pools and other water courses, in applications ncar rivers, lakes, réservoirs or seas and in applications where release to the
-3atmosphère has to be minimîsed or controlled and where damage to the atmosphère îs not désirable. Examples include use in exterior and interior paints, coatings, vamishes, waxes or other protectant layers or opacifiers, colourants or scrcens; in dyeîng, pigmentation or the use of inks; în clcaning products designed for the home, garden or industrial applications; and in 5 soap or detergent applications for industrial, home or cnvironmental usage. The compounds of the présent invention may also bc used in shampoos, houschold detergency and in household cleaners [for example oven cleaners and surface cleaners].
The compounds of the présent invention hâve exceptional dissolving power for a wide variety of agrochcmîcals, pharmaceuticals and other commercially valuable compounds, plus 10 the dissolving power also extends to dissolution of dirt, grease or waxes.
The invention is illustrated by the following Examples in which:
g = grammes °C = degrees centigrade
Unless otherwise stated, each concentration is expressed as pcrcentage by weight.
The solvents of the présent invention arc particularly effective when solubilîsing pesticides bclonging to the familles: strobilurins, triazoles and succinate dehydrogenase inhibitors (SDHI) (particularly pyrazoles; suitably pyrazam chemistry). This fact is demonstrated in the cxamples where it îs shown that the solubility of the pesticides azoxystrobin, difenoconazole and isopyrazam arc higher in the solvent propylene glycol benzoate than in a sériés of commonly used solvents. Surprisingly the solubility of cyprodinil, chlorothalonil and bicyclopyronc in propylene glycol benzoate is lower than in the same séries of common solvents. Solubilities arc quoted as pcrcentage w/w at 20°C.
EXAMPLE 1
This Example illustrâtes the high solubility of each of a number of agrochcmical active ingrédients in solvents ofthe présent invention [compounds I and 2 ofTable 1].
A glass vial was approximately one eîghth fiillcd with an active ingrédient [AI] and then solvent [in this example, propylene glycol benzoate or butylène glycol benzoate] was added until the vial was approximately one third fùll. The résultant sample was mixed with a Whirlimixer™ and was then stored at 25°C. The sample was chcckcd every few days; if there was no solid active ingrédient présent then additionaî active ingrédient was added; if there was no liquid remaining then additionaî solvent was added. This procedure was repeated until the sample had equilibrated for 4 weeks following the final addition of either active ingrédient °( or solvent. The supematent liquid layer was then analysed by gas chromotography for active ingrédient concentration; the results are given in Table 2:
Table 2
| Active Ingrédient | Solubility in propylene glycol benzoate at 25°C (%w/w) | Solubility in butylène glycol benzoate at 25°C (%w/w) |
| Dîfenoconazole | 50.5 | - |
| Chlorothalonil | 1.32 | - |
| Cyprodinil | 18.4 | - |
| 4-Hydroxy-3-[2-(2- methoxyethoxymcthyl)-6trifluoromethylpyridine-3-carbonyl]bicyclo[3.2.1 ]oct-3-cn-2-one | 27.4 | |
| Azoxystrobin | 5.5 | 8.1 |
| Cyproconazole | 4.5 | 6.9 |
| Isopyrazam | 12.7 | 12.4 |
EXAMPLE 2
This Example shows that the solvents ofthe présent invention are particularly effective when solubilisîng pesticides bclonging to the familles: strobilurîns, triazolcs and succinate dehydrogenase inhibitors (SDHI) (particularly pyrazoles; suitably pyrazam chemistry). Tables 3a and 3b show the solubility of the pesticides azoxystrobin, dîfenoconazole, isopyrazam, cyprodinil, chlorothalonil and bicyclopyrone in the solvent propylc glycol benzoate [compound 1 of Table 1], For comparison the solubilities in a sériés of commonly used solvents arc also tabulated. The data show that in most cases the propylene glycol benzoate îs a better solvent for the first three pesticides (respectively a triazole, an SDHI and a strobilurin,) than are the other common solvents. Solubilities are quoted as percentage w/w at 20C.
Table 3a
| Solvent | Dîfenoconazole | Isopyrazam | Azoxystrobin |
Of
| Propylene glycol benzoate | 50.5 | 12.7 | 5.5 |
| n-Butylbenzoate | 29.4 | 7.6 | 4.0 |
| Solvesso™ 100 ND/ULN | 37.8 | 0.0 | 1.7 |
| Solvcsso™ 200 ND/ULN | 37.7 | 5.8 | 5.6 |
| Dowanol™ PnB | 34.4 | 8.8 | 1.3 |
| Isobomyl acetate | 24.9 | 6.8 | 1.6 |
| Benzoflex™ 9-88 | 19.8 | 6.3 | 4.2 |
| Butyl lactatc | 47.1 | 16.5 | 4.6 |
| Dowanol™ PGDA | 34.1 | 6.9 | 9.4 |
| Benzyl acétone | 44.9 | 12.6 | 14.1 |
| Benzyl acetate | 46.0 | 8.9 | 13.8 |
| Triacetin | 22.3 | 4.3 | 6.4 |
Table 3b
| Solvent | Cyprodinil | Bicyclopyrone | Chlorothalonil |
| Propylene glycol benzoate | 18.4 | 27.4 | 1.3 |
| n-Butylbenzoate | 35.5 | 45.6 | 2.3 |
| Solvcsso™ 100 ND/ULN | 31.1 | 52.3 | 7.1 |
| Solvesso™ 200 ND/ULN | 34.4 | 50.7 | 9.6 |
| Dowanol4 PnB | 41.7 | 32.0 | 0.2 |
| Isobornyl acétate | 32.8 | 38.4 | 0.5 |
| Benzoflex™ 9-88 | 22.6 | 23.2 | 1.9 |
| Butyl lactate | 52.5 | 48.6 | 0.4 |
| Dowanol™ PGDA | 31.3 | 38.3 | 0.6 |
| Benzyl acetone | 39.6 | 53.0 | 2.8 |
| Benzyl acetate | 36.8 | 55.5 | 2.0 |
| Triacetin --- | - | 33.3 | 0.4 |
Claims (2)
- l. A formulation comprising a compound of formula (I) where R1 is hydrogen, methyl, ethyl, propyl or butyl; R2 is methyl or ethyl; R3 ls hydrogen, methyl or ethyl; and n is I, 2 or 3.10 2. A formulation as claimed in claim 1 where R1 is hydrogen.3. A formulation as claimed in claim 1 or 2 where R3 is hydrogen.4, A formulation as claimed in claim 1, 2 or 3 where n is 1.5, A formulation as claimed in claim 1, 2, 3 or 4 where the formulation is an cmulsifiable conccntrate or an émulsion.6. A formulation as claimed in claim 1, 2, 3, 4 or 5 where the formulation further20 comprises an agrochcmical.7, A formulation as claimed in claim 6 where the agrochemical is a strobilurin, a triazole or a succinate dehydrogenase inhibitor.25 8, A formulation as claimed in claim 7 where the agrochemical is azoxystrobin, difenoconazole or isopyrazam.9. A compound of formula (I) where R1 is hydrogen, methyl, ethyl, propyl or butyl; R2 îs methyl or ethyl; R3 is5 hydrogen, methyl or ethyl; and n is 1, 2 or 3; provided that the compound is not
- 2-hydroxypropyl benzoate, 2-hydroxy-l-methylethyl benzoatc, 1,2 butanediol -2benzoate, 1,2 butanediol-1-benzoatc or l-propanol-2(2-hydroxypropoxy)-l-benzoatc.10. A compound of formula (I) as claimed in claim 9 where R1 is hydrogen.11. A compound of formula (I) as claimed in claim 9 or 10 where R3 is hydrogen.12. A compound of formula (1) as claimed in claim 9, 10 or 11 where n is 1.15 13. A compound of formula (I) as claimed in claim 9, 10, 11 or 12 where R2 is methyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1012586.2 | 2010-07-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA16306A true OA16306A (en) | 2015-04-24 |
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