GB2041751A - Herbicidal compositions containing N min -alkoxy-N min -alkyl substituted N-phenylureas - Google Patents
Herbicidal compositions containing N min -alkoxy-N min -alkyl substituted N-phenylureas Download PDFInfo
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- GB2041751A GB2041751A GB8003607A GB8003607A GB2041751A GB 2041751 A GB2041751 A GB 2041751A GB 8003607 A GB8003607 A GB 8003607A GB 8003607 A GB8003607 A GB 8003607A GB 2041751 A GB2041751 A GB 2041751A
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- United Kingdom
- Prior art keywords
- solvent
- solution
- alkyl substituted
- linuron
- alkoxy
- Prior art date
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- Granted
Links
- 239000000203 mixture Substances 0.000 title description 29
- 230000002363 herbicidal effect Effects 0.000 title description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000002904 solvent Substances 0.000 claims abstract description 34
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims abstract description 10
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 5
- -1 aliphatic ketones Chemical class 0.000 claims abstract description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 150000003997 cyclic ketones Chemical class 0.000 claims abstract description 3
- 235000005985 organic acids Nutrition 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 150000004292 cyclic ethers Chemical class 0.000 claims abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical group CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 claims description 8
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical group CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 8
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical group CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical group O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical group COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical group CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical group CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical group CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 3
- 229940007550 benzyl acetate Drugs 0.000 claims description 3
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical group CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 claims description 2
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Chemical group CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims description 2
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical group CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims description 2
- 239000002563 ionic surfactant Substances 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical group CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 40
- 239000005573 Linuron Substances 0.000 description 39
- 238000009472 formulation Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 6
- 239000004009 herbicide Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 244000061456 Solanum tuberosum Species 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N ethylmethylbenzene Natural products CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 241000205407 Polygonum Species 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- 240000006909 Tilia x europaea Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004848 alkoxyethyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- ALLOLPOYFRLCCX-UHFFFAOYSA-N chembl1986529 Chemical compound COC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ALLOLPOYFRLCCX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
A solution of an N min -alkoxy-N min -alkyl substituted N-phenylurea, stable under storage and at temperatures down to -10 DEG C, comprising N min -alkoxyl-N min -alkyl substituted N-phenylurea 0.05 to 40% Solvent A 99.9 to 24% Solvent B 0.05 to 36% in which Solvent A is selected from one or more of dimethylformamide, dimethylacetamide, dimethylsulphoxide and Solvent B consists of one or more solvents miscible with A, other than alcohol, aliphatic acid or an aliphatic hydrocarbon. Solvent B may be selected from aromatic hydrocarbons, aliphatic ketones, cyclic ketones, cyclic ethers, esters of aromatic or aliphatic organic acids, chlorinated hydrocarbons and combinations thereof.
Description
SPECIFICATION
Herbicidal compositions containing N'-alkoxy-N'-alkyl substituted N-phenylureas
This invention relates to solutions of herbicidal N'-alkoxy-N'-alkyl substituted N-phenylureas
including those which are liquid at temperatures below OOC. in particular, the invention relates to such
solutions which are stable to stockage and which do not solidify nor allow the precipitation of solids at temperatures down to -1 00C.
N'-alkoxy-N'-alkyl substituted N-phenylureas are a well known class of herbicides. An example of
such a herbicide is Linuron, N-(3,4-dichlorophenyl)-N'-methoxy-N'-methylurea which is commercially
available and is used as a herbicide in both pre- and post--emergence stages.
Generally, these compounds are sparingly soluble in water, sparingly soluble in aliphatic and
aromatic hydrocarbons and fairly soluble in ethanol and acetone, but the solution in these solvents is
not stable over a period of time and at low temperatures they give rise to precipitation of solids. These
properties make in difficult to formulate liquid compositions based on Linuron which are stable at low
temperatures.
British Patent Specification No. 1 449 768 (Ciba-Geigy) discloses a liquid formulation consisting
of:
A) at least one herbicidal compound of the general formula: X-0-CH2-CH2-0-R in which X is an alkyl or an alkoxyethyl; R is H, an alkyl or an alkoxyalkyl,
B) another herbicide different from A), in the form of a homogeneous solution,
and, optionally an aerosol propellant, diluents, surfactants, dyes, anticorrosive agents and the like.
The Table on page 6 of the above Patent Specification discloses a composition containing 2
butoxy-ethanol as component A Linuron and Bromacil as component B, and Sudan Red (C.l. Solvent
Red 1) as a coadjuvant.
Suitable diluents are stated to be water, dimethylsulphoxide, lower alcohols, ketones, aromatic
hydrocarbons, alkylated naphthalin derivatives, benzene, toluene, xylol, aliphatic hydrocarbons;
chlorinated hydrocarbons, oxygenated hetero-cyclic compounds, carboxylic aliphatic amides and the
esters of alkanoic acids with alkanols having from 3 to 1 5 carbon atoms.
No specific mention is made in the Patent of the stability of Linuron solutions at temperatures lower than OOC nor is there any indication of the degree of solubility of the Linuron or of other N'-alkoxy
N'-alkyl substituted N-phenylureas in the indicated solvents.
It is known that Linuron and, in general, N'-alkoxy-N'-alkyl substituted N-phenylureas, are soluble in dimethylsulphoxide in quantities of up to 55% by weight. However, at low temperatures, the solution solidifies and at OOC becomes a crystalline mass.
Good stability at low temperatures is achieved when N'-alkoxy-N'-alkyl substituted Nphenylureas are dissolved in dimethylformamide or in dimethylacetamide. In the latter solvents the Nphenylureas are soluble in amounts up to 40% by weight of the solution, and the solutions prove stable even at low temperatures, however they aí e expensive and uneconomic to use when formulating N- phenylureas in the form of solutions for horticultural use.
According to the present invention there is provided a solution of an N'-alkoxyl-N'-alkyl substituted N-phenylurea, stable under storage and at temperatures down to -1 00C, comprising:
N'-alkoxy-N'-alkyl substituted
N-phenylureas 0.05 to 40%
Solvent A 99.9 to 24%
Solvent B 0.05 to 36% in which Solvent A is selected from one or more of dimethylformamide, dimethylacetamide, dimethylsulphoxide, and Solvent B consists of one or more solvents miscible with A, other than an alcohol, aliphatic acid or an aliphatic hydrocarbon.
Suitable solvents for use as Solvent B include chlorinated hydrocarbons, e.g. 1 ,2,3- trichioropropane aromatic hydrocarbons e.g. toluene, xylol, ethylbenzene, and styrene, aliphatic and cyclic ketones e.g. isophorone, methylethylketone, ethylamylketone, cyclohexanone and acetophenone, cyclic esters e.g. dioxane, esters of aliphatic or aromatic organic acids e.g. methylbenzoate, benzyl acetate, 2-ethoxy-ethylacetate, diethylmaleate, mixtures of hydrocarbons e.g. Solvesso 1 50 (trade mark of Esso Company, for a mixture based on Dimethyl-, ethyl-, and tetramethylbenzene), Shellsol AB (trade mark of Shell Company, for mixtures based on dimethyl-, ethyl- and tetramethylbenzene) and any admixture of such solvents.
The stability of such solutions is particularly surprising since the presence of solvent B, in which the N'-alkoxy-N'-alkyl substituted N-phenylureas are sparingly soluble or insoluble, does not depress the solubility of the N-phenylurea which proves about equal to that as if the whole mixture of solvents were unmixed solvent A. Moreover, while in the pure solvent B the phenylureas are unstable on storage or tend to precipitate, with the mixture of solvents A and B the mixtures are stable.
The following Table I reports the stability values of Linuron in various solvents and in the mixtures of solvents according to the invention, after 7, 14 and 30 days at 540C.
The titre was determined by liquid-gas chromatography.
TABLE I Stability tests of Linuron in various solvents and in mixtures of solvents
according to the invention, at 54"C.
Solution 7 days 14 days 30 days Linuron (*) 40% 26.6% (-32%) 22.7% (-42%) 9.8% (-75%) Isoforone 60% Linuron 40o/0 36.1% (-7.7%) 34.6% (-11.5%) 32.4%(-17.1%) Cyclohexanone 60% Linuron 40% 39.8% 40.3% 39.3% DMF 60% Linuron 40% 39.7% 40.1% 40.1% DMF 24% Xylol 36% Linuron 40% 39.4% 39.8% 39.4% DMSO 60% Linuron 40% 39.4% 40.9% 40.1% DMSO 24% Xylol 36%
(*) Technical Linuron at 97.7% concentration, corresponding to pure Linuron
at 39.1% concentration.
The solutions according to this invention, may include conventionai ionic and non-ionic surfactants and/or propellants. The solutions may also be used for preparing wettable powders and aqueous suspensions according to conventional techniques. It is possible to store such compositions prepared from solutions of the invention or to use them. under temperature conditions at which it was not possible to use similar prior art compositions. The formulations having as a base the solutions according to the present invention also show an improved activity in the field in comparison with other known herbicide formuiations containing the same quantity of Linuron, as will be demonstrated hereinafter.
The invention will now be described with reference to the following Examples.
EXAMPLE 1
0.05 g of Linuron, i.e. of the formula:
were dissolved in a mixture consisting of 99g of dimethylformamide (DMF) and 0.05 g of xylol under constant stirring for 20 minutes at 250C.
A completely clear solution was obtained of which 50 g were maintained for 30 days at a thermostabilized temperature of 540C, while the other 50 g of the solution were kept in a cell refrigerated at -1 00C. At the end of the heating and the refrigeration period both solution samples proved unaltered.
The analysis of the two samples, carried out directly on the solution by means of liquid-gas chromatography, showed that the Linuron was present in both cases in the solution in a concentration of 0.05%.
EXAMPLE 2
40 g of Linuron were dissolved in a mixture consisting of 24 g of DMF and 36 of xylol, maintaining this mixture under stirring for 20 minutes at 250C. The dissolving of the substance is very endothermic and accordingly dissolution is enhanced by the supply of heat.
A full clear solution was obtained, 50 g of which were placed for 30 days into a heating cell thermostabilized at 540 C, while a further 50 g of the solution were placed into a cell refrigerated at --1 OOC. At the end of the heating and the cooling periods, the two sample solutions proved to be
unaltered.
The analysis of the two solution samples, directly drawn from the said solution, and carried out by liquid-gas chromatography, showed that the Linuron was in both cases present in a concentration of 40% of the solution.
EXAMPLE 3
40 g of Linuron were dissolved in a mixture consisting of 24 g of dimethylsulphoxide (DMSO) and
36 g of xylol, keeping the mixture under constant stirring for 20 minutes at a temperature of 250C. The dissolving of the substance is very endothermic and accordingly is enhanced by the supply of heat.
A full clear solution was obtained, 50 g of the solution were placed for 30 days into a cell heated at a thermostabilized temperature of 540 C, while the other 50 g of the solution were placed into a cell
refrigerated at -100C. At the end of the two periods of respectively heating and cooling, the sample
solutions proved to be unaltered.
The analysis of the two solution samples was carried out on the samples of liquid gas
chromatography which revealed that the Linuron was present in both solution samples in a
concentration of 40%.
EXAMPLE 4
Following the same procedures of Examples 1,2 and 3 the solutions listed in the following Table II were prepared. 50 g samples of each solution were placed into a cell thermostabilized at 540C and further 50 g samples were placed in a refrigerating cell cooled down to -1 00C.
At the end of the respective heating and cooling periods, the two solution samples proved to have remained unaltered. The analysis of these samples, carried out directly on them by liquid-gas chromatography, showed that the Linuron was present in both solution samples in concentrations equal to the initial respective concentrations.
TABLE II
Components Compositions (g) Linuron 40 40 40 40 40 40 40 40 40 40 40 40 40 40 40 40 40 40 40 40 40 DMF 30 30 24 24 24 24 30 24 24 24 DMSO 30 30 24 24 24 24 24 24 24 24 Solvesso 150 30 30 Shellsol AB 30 30 Methylbenzolate 36 36 Benzyl acetate 36 36 Cellosolve acetate 36 36 Dioxane 36 36 1,2,3-trichloro propane 30 30 Methylethyl ketone 36 36 Cyclohexane 36 36 Acephenone 36 36 EXAMPLE 5
Following the same procedures as those of Examples 1,2, and 3 there were prepared a solution consisting of 40 g of Linuron, 25 g of dimethylacetamide and 36 g of xylol.
After maintaining the solution (two samples 50 g each) respectively for 30 days at a stabilized temperature of 540C and for 48 hours at -100C, the solution proved to have remained unaltered and the Linuron analysed by liquid-gas chromatography, was present in an amount of 40% by weight of the solution.
EXAMPLE 6
40 g of Monolinuron of the formula:
were dissolved in a mixture consisting of 24 g of dimethylformamide and 36 g of xylol, under constant stirring for 20 minutes at 250C. A full clear solution was obtained of which 50 g were maintained at a temperature stabilized at 540C for 30 days, and 50 g were maintained constantly for 30 days at --100C.
After the respective heating and cooling periods, the two solution samples were found to have remained unaltered. In both cases 10 g of solution were dried under a vacuum made by a mechanical pump, at a temperature between 70 and 750C. 4.1 gof a dry residue were obtained which upon recrystallisation exhibited a melting point of between 70 and 720C (Monolinuron melting point: 720C), while the IR spectrum coincided with the spectrum of the starting Monolinuron, thus confirming the percentage of 40% by weight of active substance introduced at the start.
EXAMPLE 7
40 g of Metabromuron of the formula:
were dissolved in a mixture consisting of 24 g of dimethylformamide and 36 g of xylol, under constant stirring for 20 minutes at a temperature of 25"C. A full clear solution was obtained of which 50 g were maintained for 30 days at a stabilized temperature of 540C and the other 50 g were maintained at --1 OOC. After the respective heating and cooling periods, both solution samples were found to have remained unaltered.
In both cases, 10 g of the solution were dried under a vacuum made by a mechanical pump, at between 70 and 750C. 4.2 of a dry residue were obtained which upon recrystallisation exhibited a melting point of between 94 and 960C (Metabromuron melting point: 95.5 to 960C) while the IR spectrum coincided with the IR spectrum of the starting Metabromuron, thus confirming the percentage of 40% by weight of active substance introduced at the beginning.
EXAMPLE 8
Following the same procedure as in Example 2 the following formulation which is concentrated emulsifyable type was prepared:
Linuron 30.0 g
DMF 22.0 g
Xylol 38.0g Emulsion TBF 10.0 g ,Using this formulation an agronimical evaluation was made which showed that a greater activity was developed compared with that exerted by a known formulation, consisting of: 50% Linuron, 20% kaolin, 20% silicon and 10% sodium ligninsulphonate.
The tests were carried out on potato cultivations (cv. Jaerla), on vines (cv. Lambrusco Marani), fruit (apple trees cv. Starling, cv. Star Crimson, cherry trees, lime trees).
The treatment was carried out pre-emergence of the weeds and, in the case of the potatoes, postsowing, after having suitable worked the soil.
The product obtained according to the present Example (OE 30) and the known formulation (wettable powder PB 50), were dispersed in 500 to 1000 litres/hectare of water. The application rate, expressed in kg of active ingredient per hectare are reported in the following Table Ill.
The tests were conducted according to the scheme of randomised batches, repeating each experiment four times, in 20 m2 plots for the potato, and in 5 to 10 m2 plots for the vineyard and the orchard.
The results were determined counting the number of weeds present on the plots.
TABLE III
Frequency/m of the various weeds Kg of active Euphorbia Chenopodium Polygonum Veronica Veronica Veronica Portulaca ingredient peplus album aviculum persica persica oleracea Product per hectare no./m no./m no./m no./m no./m no./m Linuron OE 30 0.7 3.9 0.2 0.03 3.5 1.8 4.3 Linuron OE 30 1.0 2.9 0.08 0.03 1.5 1.8 4.0 Linuron OE 30 1.2 1.0 0.08 0 0 0.3 2.7 Linuron PB 50 0.7 5.7 0.4 0.1 5.0 1.8 5.6 Linuron PB 50 1.0 2.9 0.2 0.1 1.8 2.0 5.3 Linuron PB 50 1.2 3.0 0.08 0.03 0.3 2.0 5.0 Control - 8.1 2.9 0.8 0.8 15.0 50.0 The formulation of Linuron at 30% of active principle according to the invention used in the preemergence period of the weeds in combatting the weeds present in potato cultivation, in the vineyard and in the nursery, developed at an equal application rate, a herbicide activity superior to that of the commercial wettable powder formulate. No deleterious effects could be detected on the cultivations examined.
The activity ratio between the two Linuron formulations for the tested cultivations proved to be the following: 0.750/0.800 kg of active substance from 30% Linuron OE (according to the invention) corresponds, as for its activity, to 1 kg of active substance from Linuron PB 50 (prior art).
The figures reported in Table Ill represent the average of the results obtained over all the trials.
Claims (6)
1. A solution of an N'-alkoxy-N'-alkyl substituted N-phenylurea, stable under storage and at temperatures down to -1 00C, comprising:
N'-alkoxy-N'-alkyl substituted
N-phenylurea 0.05 to 40%
Solvent A 99.9 to 24%
Solvent B 0.05 to 36% in which Solvent A is selected from one or more of dimethylformamide, dimethylacetamide, dimethylsulphoxide, and Solvent B consists of one or more solvents miscible with A, other than an alcohol, aliphatic acid or an aliphatic hydrocarbon.
2. A solution as claimed in Claim 1, in which solvent B is selected from aromatic hydrocarbons, aliphatic ketones, cyclic ketones, cyclic ethers, esters or aromatic or aliphatic organic acids, chlorinated hydrocarbons and combinations thereof.
3. A solution as claimed in Claim 2, in which solvent B is selected from xylol, toluene, dimethylethylbenzene, tetramethylbenzene, isophoron, methylethyl ketone, ethylamylketone, cyclohexanone, acetophenone, dioxane, methylbenzoate, benzylacetate, 2-ethoxy-ethylacetate, diethyl maleate, 1 2,3-trichloro-propane and combinations thereof.
4. A solution as claimed in Claim 3 in which solvent B comprises dimethyl-ethylbenzene and tetramethylbenzene.
5. A solution as claimed in any preceding claim which additionally comprises one or more ionic or non-ionic surfactants.
6. A solution of an N'-alkoxy-N'-alkyl substituted N-phenylurea as claimed in Claim 1 substantially as herein described with reference to any one of the Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19883/79A IT1110255B (en) | 1979-02-05 | 1979-02-05 | SOLUTIONS BASED ON N-PHENYLUREE N'-ALCOSSI, N'-ALCHIL REPLACED HERBICIDE STABLE AT TEMPERATURES FROM +54 C TO -10 C |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2041751A true GB2041751A (en) | 1980-09-17 |
| GB2041751B GB2041751B (en) | 1982-10-20 |
Family
ID=11162042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8003607A Expired GB2041751B (en) | 1979-02-05 | 1980-02-04 | Herbicidal compositions containing n'alkoxy-n'alkyl sustituted n-phenylureas |
Country Status (11)
| Country | Link |
|---|---|
| AU (1) | AU5511480A (en) |
| BE (1) | BE881554A (en) |
| CA (1) | CA1135523A (en) |
| CH (1) | CH641931A5 (en) |
| DE (1) | DE3004160A1 (en) |
| DK (1) | DK41080A (en) |
| FR (1) | FR2447906A1 (en) |
| GB (1) | GB2041751B (en) |
| IT (1) | IT1110255B (en) |
| LU (1) | LU82129A1 (en) |
| NL (1) | NL8000616A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0300691A2 (en) * | 1987-07-16 | 1989-01-25 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | Plant-protective composition |
| EP0515679A1 (en) * | 1990-12-18 | 1992-12-02 | Dowelanco | Precipitated flowable concentrate formulations, their preparation and their agricultural uses |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1544172A (en) * | 1967-09-20 | 1968-10-31 | British Petroleum Co | Pesticide products, oily and emulsifiable, for agricultural and industrial use |
| FR2218053A1 (en) * | 1973-02-16 | 1974-09-13 | Rhone Progil | Herbicidal emulsifiable concentrates - contg. solvent emulsifier and at least two herbicides |
-
1979
- 1979-02-05 IT IT19883/79A patent/IT1110255B/en active
-
1980
- 1980-01-24 CH CH56780A patent/CH641931A5/en not_active IP Right Cessation
- 1980-01-31 NL NL8000616A patent/NL8000616A/en not_active Application Discontinuation
- 1980-01-31 DK DK41080A patent/DK41080A/en not_active Application Discontinuation
- 1980-02-01 AU AU55114/80A patent/AU5511480A/en not_active Abandoned
- 1980-02-04 GB GB8003607A patent/GB2041751B/en not_active Expired
- 1980-02-04 LU LU82129A patent/LU82129A1/en unknown
- 1980-02-04 FR FR8002357A patent/FR2447906A1/en active Pending
- 1980-02-04 CA CA000345005A patent/CA1135523A/en not_active Expired
- 1980-02-05 BE BE0/199269A patent/BE881554A/en not_active IP Right Cessation
- 1980-02-05 DE DE19803004160 patent/DE3004160A1/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0300691A2 (en) * | 1987-07-16 | 1989-01-25 | CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. | Plant-protective composition |
| EP0300691A3 (en) * | 1987-07-16 | 1989-02-08 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Plant-protective composition |
| EP0515679A1 (en) * | 1990-12-18 | 1992-12-02 | Dowelanco | Precipitated flowable concentrate formulations, their preparation and their agricultural uses |
| EP0515679A4 (en) * | 1990-12-18 | 1993-06-09 | Dowelanco | Precipitated flowable concentrate formulations, their preparation and their agricultural uses |
Also Published As
| Publication number | Publication date |
|---|---|
| DK41080A (en) | 1980-08-06 |
| IT1110255B (en) | 1985-12-23 |
| GB2041751B (en) | 1982-10-20 |
| NL8000616A (en) | 1980-08-07 |
| AU5511480A (en) | 1980-08-14 |
| IT7919883A0 (en) | 1979-02-05 |
| CH641931A5 (en) | 1984-03-30 |
| FR2447906A1 (en) | 1980-08-29 |
| CA1135523A (en) | 1982-11-16 |
| LU82129A1 (en) | 1980-09-24 |
| DE3004160A1 (en) | 1981-01-08 |
| BE881554A (en) | 1980-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |