GB2024213A - Dihalophenoxypropionic acids and their derivatives, and their use as cotton desiccants - Google Patents
Dihalophenoxypropionic acids and their derivatives, and their use as cotton desiccants Download PDFInfo
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- GB2024213A GB2024213A GB7919586A GB7919586A GB2024213A GB 2024213 A GB2024213 A GB 2024213A GB 7919586 A GB7919586 A GB 7919586A GB 7919586 A GB7919586 A GB 7919586A GB 2024213 A GB2024213 A GB 2024213A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
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Abstract
Compounds useful for desiccating growing cotton plants and having the formula: <IMAGE> wherein R<1> and R<2> are halogen or CF3, and R<3> is OH; OM where M is a cation; or one of a variety of optionally substituted alkoxy, alkenyloxy, phenoxy, and amino radicals; provided that R<1> and R<2> can both be chlorine only when R<3> is an alkanesulphonamido radical.
Description
SPECIFICATION
Dihalophenoxypropionic acids and their derivatives, and their use as cotton desiccants
This invention relates to dihalophenoxypropionic acids and their derivatives useful for desiccating cottonplants, to a process for preparing these compounds, to cotton desiccating compositions containing them and to a method of desiccating cotton using them.
In the mechanical harvesting of cotton crops, the presence of green leaves and stems on the cotton plants is disadvantageous, since the leaves and stems tend to be crushed during the harvesting operation, and to leave green stains on the cotton. Accordingly it is general practice to spray the crop, at a convenient interval before harvesting, with a chemical desiccant in order to dry up the green leaves and stems.
Our British Patent Application No. 9878/77 relates to the use as desiccants for cotton of compounds of general formula (I):
wherein R is hydroxy, a group of general formula -OM wherein M is a cation, or one of a variety of optionally substituted alkoxy, alkenyloxy, phenoxy and amino groups. We have now discovered a further class of compounds having cotton desiccating activity.
Accordingly, the present invention provides a compound of general formula (all):
wherein each of R1 and R2, which may be the same or different, is halogen or halo (C1.6 alkyl) (e.g.
trifluoromethyl); and R3 is hydroxy; a group of general formula -OM wherein M is a cation; phenoxy optionally substituted with at least one substituent selected from the class consisting of halogen and C1-4 alkyl; cycloalkoxy. alkoxy optionally substituted with at least one substituent selected from the class consisting of chlorine, hydroxy, alkoxy, dialkylamino, optionally chloro-, phenoxy- or methyl- substituted phenyl and a group of general formula (III):
wherein R1 and R2 are as defined above; alkenyloxy; alkylthio optionally substituted with optionally chloroor methyl-substituted phenyl; alkenylthio; or a group of general formula -NR4R5 wherein R4 is hydrogen, alkoxy, alkyl, alkenyl, phenyl or mono- or di-alkylamino, and R5 is hydrogen, alkyl, alkenyl or alkanesulphonyl, or R4 and R5 form, together with the nitrogen to which they are attached, a pyrrolidine or piperidine ring; subject to the proviso that R1 and R2 are both chlorine only when R3 is a group of formula -NR4R5 wherein R4 is hydrogen and R5 is alkanesulphonyl.
In this specification, the terms "halogen" and "halo" refer only to fluorine, chlorine, bromine and iodine.
When M is a cation it may be for example an alkali metal or an alkaline earth metal cation, for example a sodium, potassium, calcium or magnesium cation. M can also be an ammoniun cation or a mono-, di-, tri- or tetra- substituted ammonium cation in which the substituents may be, for example, C1-6 aliphatic groups.
e.g. Cis alkyl groups.
When R3 is alkoxy, it may be for example C1-20 alkoxy, for example C1-12 alkoxy e.g. methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy and dodecyloxy. When R3 is substituted alkoxy, it may be benzyloxy optionally substituted by at least one chlorine or methyl, for example 2chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy, 2,4-dichlorobenzyloxy, 4-methyl benzyloxy or 4phenoxybenzyloxy.The substituted alkoxy groups can also be alkoxy substituted by at least one hydroxy, alkoxy (for example C1 4 alkoxy), chlorine, dialkylamino or a group of general formula (III) as defined above, e.g. 2-hydroxyethoxy, 2-chloroethoxy, 2-diethylaminoethoxy, 2-ethoxyethoxy, 2-butoxyethoxy or dibromophenoxy)propionyloxy]ethoxy. When R is cycloalkoxy, it is suitably C3.s cycloalkoxy e.g.
cyclohexyloxy.
When R3 is alkenyloxy, it may be C320 alkenyloxy e.g. C3.2 alkenyloxy; examples are allyloxy and octadecenyloxy.
Examples of alkylthio groups are C1-12 alkylthio, e.g. methylthio and ethylthio. Examples of substituted alkylthio groups are benzylthio optionally ring-substituted with at least one methyl or chlorine, for example 2-chlorobenzylthio, 3-chlorobenzylthio, 4-chlorobenzylthio, and 4-methylbenzylthio.
Examples of the alkenylthio radicals are C3-12 alkenylthio, e.g. allythio.
When R4 is alkoxy, it may be for example C1 l2 alkoxy, e.g. methoxy. When R4 is alkyl, it may be for example methyl, ethyl, propyl or butyl. When R4 is alkenyl, it may be for example allyl or but-2-enyl. When R4 is mono- or di-alkylamino, the alkyl can be ClA alkyl. When R5 is alkyl, it may for example be C1 4 alkyl. When
R5 is alkenyl, it may be allyl or but-2-enyl. When R5 is alkanesulphonyl, it may be for example C1 4 alkanesulphonyl e.g. methanesulphonyl.
Examples of the compounds of general formula (II) are listed in Table I.
TABLE I
Compound Melting (or
No R1 R2 R3 Boiling) Point ( C)
1 Br Br EtO- (118-123 /0.2Torr) 2 Br Br H2N- 142
3 Br Br HO- 143
4 Br Br C6H5CH2o- 52
5 Br CI Eto- (106-107 /0.4 Torr)
6 Cl Br EtO- (116-117 /0.4Torr) 7 Br Cl HO- 143 8 Cl Br HO- 135 9 Cl CF3 Me2N- 62-63 10 Br Br Me2N- 84 11 Br CI Me2N- 76 12 Cl Br Me2N- 88 13 Cl I Me2N- 105 14 Cl Br C6H5CH2O- 48-50 15 Br I EtO- 40 16 BR I C6H5CH2O17 Br I Me2N- 109 18 Cl I EtO- (1500/0.1 Torr) 19 CI CF3 EtO- (77780/0.6 Torr) 20 Br Cl C6H5CH2O- 49530 21 Br Br MeS(O)2NH- 144-145 22 Br Br p-CI-C6H4CH20- 48-52 23 Br Br p--C6H5O-C5H4CH2O- oil
The compounds of general formula (II) may, if desired, be applied in admixture with other herbicides to desiccate cotton. Examples of these other herbicides are salts of the bipyridylium herbicides paraquat and diquat. Paraquat and diquat are the accepted common names for the 1,1 '-dimethyl-4,4'-bipyridylium cation and the 1,1 '-ethylene-2,2'-bipyridylium cation, respectively.
The particular salt of paraquat or diquat used is not critical. Conveniently the salt is one which is readily soluble in water. Examples of suitable paraquat salts are the chloride, bromide, iodide, methylsulphate, sulphate, methylphosphate, and phosphate while examples of suitable diquat are the chloride, bromide, iodide, methylsulphate, sulphate, phosphate and p-toluenesulphonate. Since the characteristic herbicidal activity of paraquat and diquat salts resides in the paraquat or diquat cation only, it is customary to quote.
concentrations of active ingredient and rates of application in terms of the amount of paraquat cation or diquat cation used, thus avoiding the inconvenience of having to quote different application rates for different salts of paraquat or diquat. Application rates and concentrations quoted in this Specification therefore relate to the amount of paraquat or diquat cation unless otherwise stated.
The rate at which the compounds of general formula (II) are applied to desiccate cotton depends upon a variety of factors, for example the identity of the particular compound chosen for use, but in general the rate is 0.06 to 1.0, e.g. 0.1 to 0.5, kilograms per hectare. When applied in admixture with paraquat or diquat, the amount of the compound can be correspondingly reduced; usually up to half or more of the weight of the compound can be replaced by the same weight of paraquat or diquat. Thus, instead of using 0.5 kilograms per hectare of the compound, a mixture of the compound and paraquat could be applied, each at a rate of 0.25 kilograms per hectare. An advantage of using the mixture is that the desiccation process is more rapid than when the compound is used alone.
The compounds are preferably applied in the form of compositions, in which the active ingredient is mixed with a carrier comprising a solid or liquid diluent. Preferably, a surface-active agent is also present.
Conveniently, the compound is applied in the form of a solution or dispersion in water, together with a surface-active agent. When applied together with paraquat or diquat, the spray composition may comprise a solution of the compound in a water-immiscible organic solvent which has been emulsified with an aqueous solution of paraquat or diquat, the mixture containing a surface-active agent to assist in its emulsification.
Examples of water-immiscible organic solvents include hydrocarbon solvents, for example alkyl-substituted benzenes, and chlorinated hydrocarbons, for example ethylene dichloride.
The compounds are preferably applied in the form of compositions in which the active ingredient is mixed with a carrier comprising a solid or liquid diluent. Preferably a surface-active agent is also present.
Conveniently, the compounds are applied in the form of a solution or dispersion in water, together with a surface-active agent.
Surface active agents may be of the cationic, anionic or non-ionic type. Suitable cationic agents are quaternary ammonium compounds, for example cetyltrimethyl ammonium bromide. Suitable anionic agents are soaps, salts of aliphatic monoesters of sulphuric acid, for example sodium lauryl sulphate, and salts of sulphonated aromatic compounds, for example dodecylbenzenesulphonate, sodium, calcium and ammonium lignosulphonate, butyl-napthalene sulphonate, and a mixture of the sodium salts of diisopropyl and triisopropyl-napthalenesulphonic acid. Suitable non-ionic agents are the condensation products of ethylene oxide with fatty alcohols such as oleyl alcohol and cetyl alcohol, or with alkylphenols such as octyphenol, nonylphenol, and octylcresol.Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, for example sorbitol monolaurate; the condensation products of the said partial esters with ethylene oxide and the lecithins. When preparing compositions containing paraquat or diquat, anionic surface-active agents are generally to be avoided since they may interact unfavourablywith these cationic herbicides.
For convenience in transport, storage and sale, there may be prepared concentrated compositions containing a high proportion of active ingredient, for example 10 to 85%, and 25 to 60%, by weight of active ingredient. These concentrates are diluted with water before use.
The compounds of general formula (II) may be made by conventional methods known in the art. The invention provides a process for preparing a compound of general formula (II), the process comprising
(1) when a compound of general formula (II) wherein R3 is a group of.general formula -OM as defined above, optionally substituted phenoxy, cycloalkoxy, optionally substituted alkoxy, alkenylthio, alkenyloxy, or optionally substituted alkylthio is required, reacting a compound of general formula (IV)
wherein R1 and R2 are as defined above, with a compound of general formula (V)
R3 is as defined above and X is halogen (e.g. chlorine or bromine); or
(2) when a compound of general formula (II) wherein R3 is hydroxy is required, hydrolysing a compound of general formula (II) wherein R3 is as defined above other than hydroxy; or
(3) when a compound of general formula (II) wherein R3 is a group of general formula -NR4R5 as defined above is required, reacting a compound of general formula (VI)
wherein R1 and R2 are as defined above, and Xa is halogen (e.g. chlorine or bromine), with a compound of general formula (VIII)
HNR4R5 (Vll) wherein R4 and R5 are as defined above;;
and when R3 in the compound of general formula (II) obtained in (1), (2) or (3) is not the desired group, converting it in known manner to give the compound of general formula (Il) wherein R3 is the desired group.
Process (1) is suitably performed in the presence of a base, e.g. an alkali metal hydroxide or carbonate, for example potassium carbonate, and should be present in an amount which is substantially equimolarwith the other reactants. Preferably the reaction is carried out in an inert solvent, e.g. methyl ethyl ketone. The reaction may be accelerated by heating.
The acids from process (2) may be used as intermediates to obtain other compounds of general formula (II). Thus, by reaction with the appropriate alcohol, they may be converted according to standard methods to the compounds of general formula (II) wherein R3 is, for example, alkoxy or alkenyloxy.
The invention also provides cotton desiccating compositions containing a compound of general formula (II) and a carrier or diluent.
It also provides a method of desiccating growing cotton plants, which method comprises applying to the foiiage of the plants a compound of general formula (II).
The invention is illustrated by the following Examples, in which all temperatures are in degrees Centigrade and all parts are by weight unless otherwise specified.
EXAMPLE 1
This Example illustrates the use of the compounds of general formula (II) for desiccating cotton.
Each compound was formulated for test by dissolving it in cyclohexanone containing 33.3 grams per litre of Synperonic NPE 1800 (a surface-active agent comprising a condensate of one molar proportion of nonylphenol with 33 molar proportions of propylene oxide and 13 to 15 molar proportions of ethylene oxide) and 16.7 grams per litre of Tween 85 (a surface-active agent comprising a condensate of one molar proportion of sorbitan tri-oleate with twenty molar proportions of ethylene oxide). The cyclohexanone solution so prepared contained 1 gram of the compound per litre, calculated as the free acid. The solution was then diluted to 10 times its volume with cyclohexanone to give a stock solution. Samples of this were then dispersed in water to prepare emulsions for spraying.The spray emulsions so prepared were sprayed on to young rape, soya, and cotton plants grown in plastic pots of soil in the glass house. The rape plants were at the two true leaf stage, the soya plants had from one to two trifoliate leaves, and the cotton plants had two to three true leaves. The spray volume was equivalent to 200 litres per hectare. Twenty days after spraying, the extent of desiccation of the plants was assessed on a scale of 0 to 10. Each result given in Table
II is the average value for three plants, rounded off to the nearest whole number.
TABLE Il Test Plants
Compound Rate of
No. Application, kg/ha
Rape Soya Cotton 10.05 1 0 3
0.1 4 0 4
0.5 8 4 9
1.0 9 5 9
2.0 10 8 9
4 0.05 2 0 9
0.1 3 0 8
0.5 7 5 10
1.0 9 6 10
2.0 10 8 10
5 0.05 1 0 1
0.1 2 0 3
0.5 8 5 8
1.0 9 6 9
2.0 9 8 10
6 0.05 2 0 3
0.1 2 1 4
0.5 9 6 8
1.0 10 8 9
2.0 10 10 9
9 0.1 0 0 1
0.5 0 0 0
1.0 0 0 3
2.0 0 2 4
5.0 0 4 8
10 0.1 0 0 0
0.5 0 0 1
1.0 0 0 6
2.0 0 2 6
5.0 0 5 9 11 0.1 0 0 2
0.5 0 0 1
1.0 0 1 7
2.0 0 1 9
5.0 1 6 10 12 0.1 0 0 0
0.5 0 0 2
1.0 0 0 1
2.0 0 2 9
5.0 2 5 9 13 0.1 0 0 0
0.5 0 1 0
1.0 0 1 3
2.0 0 2 7
5.0 1 5 8 14 0.05 2 0 6
0.1 2 1 7
0.5 10 7 10
1.0 10 10 10
2.0 10 10 10 15 0.05 2 0 1
0.1 3 0 2
0.5 6 2 8
1.0 8 4 9
2.0 9 7 9 16 0.05 2 0 7
0.1 3 0 8
0.5 6 2 9
1.0 8 5 10
2.0 9 6 10 17 0.1 0 0 0
0.5 0 0 1
1.0 0 0 1
2.0 0 1 6
5.0 0 4 8 18 0.05 2 0 3
0.1 4 0 3
0.5 9 5 8
1.0 10 8 8
2.0 10 8 9 19 0.05 1 1 1
0.1 1 .1 1
0.5 6 3 2
1.0 10 7 6
2.0 10 10 9 20 0.05 0 0 6
0.1 2 0 9
0.5 5 3 10
1.0 9 9 10
2.0 10 9 10
EXAMPLE 2
Benzyl (2,5-dibromophenoxy)propionate (Compound No. 4)
Stage 1
2-Bromopropionyl chloride (213.4g) was added dropwise to benzyl alcohol (145.8g) with stirring under a stream of nitrogen, keeping the temperature of the reaction mixture below300C by cooling with cqld water.
When all the acid chloride has been added, the mixture was stirred for another two hours at ambient temperature. The reaction mixture was then diluted with diethyl ether (200 ml) and washed with water until free of acid. The ethereal solution was dried and evaporated and the residue distilled to give benzyl 2-bromopropionate, b.p. 82-85"/0.5 Torr.
Stage 2
2,5-Dibromophenol (53g) and benzyl 2-bromopropionate (48.69) in methyl iso-butyl ketone (250 ml) containing suspended potassium carbonate (13.89) was heated under refiux with stirring overnight. The mixture was cooled to 40% 5% sodium hydroxide solution (100 ml) was added, and the mixture was stirred to dissolve the solid potassium bromide. The aqueous phase was separated with fresh methyl iso-butyl ketone (50 ml). The combined extracts were washed with water (50 ml), dried, and evaporated under reduced pressure. The residue was distilled and the benzyl (2,5-dibromophenoxy)propionate collected at 180185c/O.5 Torr.On cooling, the distillate solidified and had a melting point of 52"C. Compounds 1,5,6, 14to 16, 18to 20,22 and 23 were made by a similar procedure.
EXAMPLE 3 2(2-Bromo-5-ch/orophenoxy}-N,N-dimethy/propionamide (Compound no.11)
2-Bromo-5-chlorophenol (89), 2-bromo-N,N-dimethyl-propionamide (6.66g) and anhydrous potassium carbonate (2.6g) in methyl iso-butyl ketone (100 ml) were refluxed with stirring overnight. The mixture was cooled to 500 and washed with 5% sodium hydroxide (2 x 20 ml) and then water (2 x 50 ml). The organic solution was dried and evaporated under reduced pressure to yield a pale red oil, which solidified on cooling. Recrystallisation from 50% aqueous ethanoi gave the title compound, m.p. 76-77". Compounds 2,9, 10 to 13, 17 and 21 were made by a similar procedure.
Claims (14)
1. A compound of general formula (II)
wherein each of R7 and R2, which may be the same or different, is halogen or halo (C1.6 alkyl); and R3 is hydroxy; a group of general formula -OM wherein M is a cation; phenoxy optionally substituted with at least one substituent selected from the class consisting of halogen and C1.4 alkyl; cycloalkoxy; alkoxy optionally substituted with at least one substituent selected from the class consisting of chlorine, hydroxy, alkoxy, dialkylamino, optionally chloro-, phenoxy- or methyl substituted phenyl and a group of general formula (III):
wherein R1 and R2 are as defined above; alkenyloxy; alkylthio optionally substituted with optionally chloroor methyl-substituted phenyl; alkenylthio; or a group of general formula -NR4R6 wherein R4 is hydrogen, alkoxy, alkyl, alkenyl, phenyl or mono- or di-alkylamino, and R5 is hydrogen, alkyl, alkenyl or alkanesulphonyl, or R4 and R6 form, together with the nitrogen to which they are attached, a pyrrolidine or piperidine ring; subject to the proviso that R1 and R2 are both chlorine only when R3 is a group of formula -NR4R5 wherein R4 is hydrogen and R5 is alkanesulphonyl.
2. A compound according to claim 1 wherein R1 is chlorine or bromine and R2 is chlorine, bromine, iodine or trifluoromethyl.
3. A compound according to claim 1 or 2 wherein R3 is hydroxy, ethoxy, benzyloxy, p-chlorobenzyloxy, p-phenoxybenzyloxy, amino, dimethylamino or methanesulphonamido.
4. A compound according to claim 1 which is any one of Compounds 1 to 23 of Table I hereinbefore.
5. A process for preparing a compound according to any one of the preceding claims, the process comprising
(1) when a compound of general formula (II) wherein R3 is a group of general formula -OM as defined in claim 1, optionally substituted phenoxy, cycloalkoxy, optionally substituted alkoxy, alkenylthio, alkenyloxy, or optionally substituted alkylthio is required, reacting a compound of general formula (IV)
wherein R1 and R2 are as defined in claim 1, with a compound of general formula (V)
R3 is as defined above and Xis halogen; or
(2) when a compound of general formula (II) wherein R3 is hydroxy is required, hydrolysing a compound of general formula (II) wherein R3 is as defined in claim 1 other than hydroxy; or
(3) when a compound of general formula (II) wherein R3 is a group of general formula -NR4R5 as defined in claim 1 is required, reacting a compound of general formula (Vl)
wherein R1 and R2 are as defined in claim 1, and X' is halogen, with a compound of general formula (VII)
HNR4R5 (all) wherein R4 and R5 are as defined in claim 1;
and when R3 in the compound of general formula (II) obtained in (1), (2) or (3) is not the desired group, converting it in known manner to give the compound of general formula (II) wherein R3 is the desired group.
6. A process according to claim 5 substantially as described in Example 2 or 3.
7. A compound of general formula (Il) prepared by a process according to claim 5 or 6.
8. A cotton desiccating composition comprising a compound of general formula (II) according to any one of claims 1 to 4 and 7, and a carrier or diluent.
9. A composition according to claim 8 comprising also a salt of paraquat or diquat.
10. A composition according to claim 9 containing 1 to 4 parts by weight of the compound of general formula (II) to one part of paraquat or diquat.
11. A composition according to claim 9 or 10 which is in the form of a solution ofthe compound of general formula (II) in a water-immiscible organic solvent, the solution being dispersed in an aqueous solution of the salt of paraquat or diquat in the presence of a surface-active agent to form an emulsion.
12. A composition according to claim 8 substantially as described herein.
13. A method of desiccating growing cotton plants, the method comprising applying to the foliage of the plants, a compound according to any one of claims 1 to 4 and 7 or a composition according to any one of claims 8 to 12.
14. A method according to claim 13 substantially as described herein.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7919586A GB2024213B (en) | 1978-06-30 | 1979-06-05 | Dihalophenoxypropionic acids and their derivatives and their use as cotton desiccants |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7828420 | 1978-06-30 | ||
| GB7919586A GB2024213B (en) | 1978-06-30 | 1979-06-05 | Dihalophenoxypropionic acids and their derivatives and their use as cotton desiccants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2024213A true GB2024213A (en) | 1980-01-09 |
| GB2024213B GB2024213B (en) | 1982-09-08 |
Family
ID=26268089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7919586A Expired GB2024213B (en) | 1978-06-30 | 1979-06-05 | Dihalophenoxypropionic acids and their derivatives and their use as cotton desiccants |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2024213B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088066A1 (en) * | 1982-02-01 | 1983-09-07 | Monsanto Company | 3,5-Bis (trifluoromethyl) phenoxy carboxylic acids and derivatives thereof |
| US4994616A (en) * | 1987-05-01 | 1991-02-19 | Ube Industries, Ltd. | Anilide herbicides |
-
1979
- 1979-06-05 GB GB7919586A patent/GB2024213B/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0088066A1 (en) * | 1982-02-01 | 1983-09-07 | Monsanto Company | 3,5-Bis (trifluoromethyl) phenoxy carboxylic acids and derivatives thereof |
| US4416687A (en) * | 1982-02-01 | 1983-11-22 | Monsanto Company | 3,5-Bis (trifluoromethyl)phenoxy carboxylic acids and derivatives thereof |
| US4994616A (en) * | 1987-05-01 | 1991-02-19 | Ube Industries, Ltd. | Anilide herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2024213B (en) | 1982-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940605 |