GB2257044A - Aryloxy benzotriazole herbicidal compositions - Google Patents
Aryloxy benzotriazole herbicidal compositions Download PDFInfo
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- 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
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Abstract
A herbicidal composition comprises an active compound as defined in EP-A-355049 or EP-A-367242 in combination with an adjuvant selected from silicon polymers, oil based spray adjuvants, alcohol ethoxylates, nonyl phenol ethoxylates, amine ethoxylates, blended surfactants, alkoxylated amines, alkyl glucosides, sulphated oils, urea ammonium nitrate, Azone and DASH. The adjuvant allows the rate of herbicide to be reduced significantly without losing the benefit of the overall control.
Description
HERBICIDAL COMPOSITIONS
The present invention relates to herbicidal compositions comprising an aryloxy benztriazole herbicide in combination with adjuvants.
EP-A-355049 and EP-A-367242 disclose aryloxy benztriazole derivatives which have herbicidal activity. EP-A-355049 also describes how these compounds may be used with certain adjuvants. The subject matter of these applications is incorporated by reference.
The applicants have found that unexpectedly good results may be obtained by mixing compounds of EP-A-355049 or EP-A-367242 with certain types of adjuvants in particular.
According to the present invention there is provided a herbicidal composition comprising a compound as defined in EP-A-355049 or EP-A-367242 in combination with an adjuvant.
Particularly suitable adjuvants for use in the compositions of the invention are those selected from the following groups:
A. Silicon polymers such as Silwet L77 , Q2 5152, X2 5309, Abil ZP2434;
B. Oil based spray adjuvants such as Atplus 411F, Atplus 412, Canplus 328, Spraymate, Orchex 796;
C. Alcohol ethoxylates such as Atlox 4848, Synperonic A7, Synperonic
91/6, Synperonic A20;
D. Nonyl phenol ethoxylates such as Agral 90;
E. Amine ethoxylates such as Synprolam 35xlO and Ethoquad C15;
F. Blended surfactants such as Atplus 300F; G. Alkoxylated amines such as Acer 89001 and Acer 89002;
H. Miscellaneous adjuvents such as alkyl glucosides and sulphated oils
such as calsolene oil HS; urea ammonium nitrate; Azone and DASH.
Preferred adjuvants are Silwett L77, X25309, Atplus 411F, Atlox 4848,
Synperonic A7 and DASH.
Preferred aryloxy benztriazole derivatives for use in the compositions are those of formula (I):
where R1 and R2 are selected from hydrogen or halogen;
R3 is haloalkyl such as trifluoromethyl and 4
R is a group
where R5 and R6 are hydrogen or lower alkyl, R7 is (CH2)n where n is 0, 1 9 9 or 2 and R8 is a carboxylic acid or ester group such as C02R9 where R is hydrogen or lower alkyl.
Preferably n is 0.
Examples of halogen groups for R1 and R2 are chlorine and fluorine.
As used herein, the term 'lower' alkyl includes C(16)alkyl in particular C13 alkyl.
Examples of R9 are methyl and ethyl.
Other preferred groups of aryloxybenztriazole herbicides are set out in EP-A-355049 and EP-A-367242.
It has been found that by employing the compositions of the invent ion, the rates of the herbicide required, can be reduced significantly without losing the benefit of the overall control.
The compositions of the invention are active as herbicidally and therefore, in a further aspect the invention provides a process for severely damaging or killing unwanted plants which process comprises applying to the plants, or to the growth medium of the plants, a herbicidally effective amount of a composition comprising an aryloxy benztriazole herbicide as hereinbefore defined and an adjuvant as hereinbefore defined.
The compositions are active against a broad range of weed species including monocotyledonous and dicotyledonous species. They are therefore useful for broad spectrum weed control in TVC (total vegetation control) situations. The composition of the invention may be applied directly to the plant (post-emergence application) or to the soil before the emergence of the plant (pre-emergence application). They are particularly useful when applied post-emergence.
The compositions of the invention may be used on their own to inhibit the growth of, severely damage, or kill plants but are preferably used with the form which further comprises a carrier comprising a solid or liquid diluent.
Compositions of the invention include both dilute compositions, which are ready for immediate use, and concentrated compositions, which require to be diluted before use, usually with water. Preferably the compositions contain from 0.01% to 90% by weight of the active ingredient. Dilute compositions ready for use preferably contain from 0.01% to 2% of active ingredient, while concentrated compositions may contain from 20% to 90% of active ingredient, although from 20% to 70% is usually preferred.
The solid compositions may be in the form of granules, or dusting powders wherein the active ingredient is mixed with a finely divided solid diluent, e.g. kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth and gypsum. They may also be in the form of dispersible powders or grains, comprising a wetting agent to facilitate the dispersion of the powder or grains in liquid. Solid compositions in the form of a powder may be applied as foliar dusts.
Liquid compositions may comprise a solution or dispersion of an active ingredient in water optionally containing a surface-active agent, or may comprise a solution or dispersion of an active ingredient in a water-immiscible organic solvent which is dispersed as droplets in water.
Surface-active agents may be of the cationic, anionic, or non-ionic type or mixtures thereof. The cationic agents are, for example, quaternary ammonium compounds (e.g. cetyltrimethylammonium bromide). Suitable anionic agents are soaps; salts of aliphatic mono ester of sulphuric acid, for example sodium lauryl sulphate; and salts of sulphonated aromatic compounds, for example sodium dodecylbenzenesulphonate, sodium, calcium, and ammonium lignosulphonate, butylnaphthalene sulphonate, and a mixture of the sodium salts of diisopropyl and triisopropylnaphthalenesulphonic 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 octyl- or nonyl- phenol (e.g. Agral 90) or octyl-cresol. Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, for example sorbitan monolaurate; the condensation products of the partial ester with ethylene oxide; the lecithins; and silicone surface active agents (water soluble surface active agents having a skeleton which comprises a siloxane chain).
The aqueous solutions or dispersions may be prepared by dissolving the active ingredient in water or an organic solvent optionally containing wetting or dispersing agent(s) and then, when organic solvents are used, adding the mixture so obtained to water optionally containing wetting or dispersing agent(s). Suitable organic solvents include, for example, ethylene di-chloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, the xylenes and trichloroethylene.
The compositions for use in the form of aqueous solutions or dispersions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, and the concentrate is then diluted with water before use. The concentrates are usually required to withstand storage for prolonged periods and after such storage, to be capable of dilution with water to form aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Concentrates conveniently contain 20-90%, preferably 20-70%, by weight of the active ingredient(s). Dilute preparations ready for use may contain varying amounts of the active ingredient(s) depending upon the intended purpose; amounts of 0.01% to 10.0% and preferably 0.1% to 2%, by weight of active ingredient(s) are normally used.
A preferred form of concentrated composition comprising the active ingredient which has been finely divided and which has been dispersed in water in the presence of a surface-active agent and a suspending agent.
Suitable suspending agents are hydrophilic colloids and include, for example, polyvinylpyrrolidone and sodium carboxymethylcellulose, and the vegetable gums, for example gum acacia and gum tragacanth. Preferred suspending agents are those which impart thixotropic properties to, and increase the viscosity of the concentrate. Examples of preferred suspending agents include hydrated colloidal mineral silicates, such as montmorillonite, beidellite, nontronite, hectorite, saponite, and saucorite. Bentonite is especially preferred. Other suspending agents include cellulose derivatives and polyvinyl alcohol.
The rate of application of the compositions of the invention will depend on a number of factors including, for example, the compounds chosen for use, the identity of the plants whose growth is to be inhibited, the formulations selected for use and whether the compound is to be applied for foliage or root uptake. As a general guide, however, an application rate of from 0.001 to 20 kilograms per hectare of total active ingredient is suitable while from 0.025 to 10 kilograms per hectare of total active ingredient may be preferred.
Preferably the compositions of the invention will contain 0.1-1% v/v of adjucants in the spray solution.
EXAMPLE 1
The following test was carried out to determine the effect of Compound
No. 12 in EP-A-355049 in combination with adjuvants for the control of a range of weed species. A 10% formulation of compound No. 12 was prepared with :
g/l
Calcium dodecyl benzene sulphonate 50
Synperonic NP13 50
Acteophenone 400
Solvesso 150 to 1 litre
The formulation alone and tank mixed in the appropriate proportions with adjuvants was then sprayed using the following methodology.
The treatments were prepared in 25ml volumetric flasks. The flasks were 2/3rd filled with deionised water and the required volume of formulated Compound No. 12 was pipetted into the flask. The adjuvants were then pipetted into the flasks to produce the required concentration as a percentage of the spray solution (25mls). The flasks were then made up to volume with deionised water, shaken and applied.
The treatments were applied in a track-spraying cabinet at a pressure of 30 p.s.i. using a single 8001E jet previously calibrated to deliver 2001/ha at the required spray height.
The % control at 14 days after application are given in Table I, and the full names of the tested plants are given in Table IX.
TABLE I
TREATMENT RATE PERCENT WEED CONTROL
g/ha 14 DAYS AFTER TREATMENT AG AV EI LL ST CA GA 00
Compound No 12 15.6 5.0 5.0 23.3 5.0 58.3 8.3 45.0
31.2 13.3 16.7 56.7 23.3 70.0 73.3 85.0
62.5 35.0 66.7 76.7 60.0 90.0 85.0 95.0 53.3
125 61.7 88.3 95.0 97.7 96.3 86.7 99.0 68.3
250 96.3 99.0 97.0 99.0 99.0 93.3 99.0 75.0
500 94.7 99.0 99.0 99.0 99.3 95.0 99.0 90.0
TABLE I (continued)
TREATMENT RATE PERCENT WEED CONTROL
g/ha 14 DAYS AFTER TREATMENT AG AV EI LL ST CA GA 00
Compound No 15.6 43.3 45.0 89.0 36.7 83.3 76.7 96.0 12 31.2 81.7 83.3 91.7 79.7 96.0 81.7 96.3 + 0.2% 62.5 83.0 94.7 99.0 97.7 96.3 90.0 99.0 50.0
Silwett L77 125 99.0 99.0 99.0 99.0 99.0 94.7 99.0 65.0
250 99.0 99.0 99.0 97.7 99.3 95.0 99.0 73.3
500 99.0 99.0 99.0 99.0 99.7 95.0 99.0 90.0
Compound No 15.6 55.0 38.3 89.7 55.0 91.7 68.3 99.0 12 31.2 81.7 76.7 99.0 81.7 96.3 88.3 99.0 + 1% 62.5 97.7 97.7 97.7 99.0 99.0 93.3 99.0 65.0
Atplus 411F 125 99.0 99.0 99.0 99.0 99.3 96.3 99.0 65.0
250 99.0 99.0 99.0 99.0 99.3 93.3 99.0 75.0
500 99.0 99.3 99.0 99.0 99.3 95.0 99.0 90.0
Example 2
In this text compound 15 of EP-A-355049 was evaluated using a dispersion of the Compound in 2.5% by volume of the dispersant used in
Example 1. The methodology used was as in Example 1, but with weed control being assessed 15 days after treatment.
The results are set out in Table II.
TABLE II
TREATMENT RATE PERCENT WEED CONTROL
g/ha 14 DAYS AFTER TREATME AG AV DG EI LL ST GA PI SM
Compound 15 15.6 1.0 30.0 5.0 17.5 60.0 42.5
31.2 10.0 17.5 37.5 12.5 7.5 27.5 62.5 76.5 82.0
62.5 27.5 60.0 55.0 27.5 5.0 45.0 81.5 100 100
125 60.0 100 75.0 42.5 35.0 60.0 75.0 99.5 100
250 70.0 100 75.0 67.5 35.0 75.0 99.5 100 100
500 85.0 90.0 99.5
TABLE II (continued)
TREATMENT RATE PERCENT WEED CONTROL
g/ha 14 DAYS AFTER TREATME AG AV DG EI LL ST GA PI SM
Compound 15 7.8 5.0 22.5 17.5 27.5 52.5 22.5
+0.2% 15.6 7.5 22.5 22.5 15.0 2.5 42.5 79.5 72.5 57.5
Agral 90 31.2 50.0 27.5 42.5 20.0 7.5 35.0 72.5 85.0 89.5
62.5 50.0 82.5 60.0 25.0 17.5 57.5 77.5 90.0 90.0
125 72.5 90.0 60.0 37.5 47.5 70.0 99.5 100 100
250 97.0 74.5 99.5
Compound 15 7.8 2.0 10.0 15.0 35.0 67.5 +0.2% 15.6 12.5 32.5 22.5 25.0 5.0 32.5 62.5 61.5 80.0 Silwet L77 31.25 10.0 37.5 25.0 15.0 10.0 37.5 80.0 79.0 99.5
62.5 52.5 65.0 55.0 35.0 7.5 55.0 75.0 85.0 100
125 92.0 92.0 65.0 62.5 57.5 67.5 99.5 99.0 100
250 94.5 90.5 100
Compound 15 7.8 18.5 22.5 17.5 30.0 70.0 50.0 + 0.2% 15.625 12.5 22.5 22.5 15.0 10.0 32.5 67.5 70.0 60.0
HD373 31.25 37.5 99.0 62.5 30.0 10.0 45.0 80.0 76.5 99.5
62.5 50.0 94.0 65.0 42.5 10.0 60.0 67.5 100 100
125 87.5 94.0 70.0 65.0 65.0 75.0 74.0 100 99.5
250 87.5 82.5 99.5
Compound 15 7.8 89.5 35.0 17.5 22.5 60.0 45.0 + 1% 15.6 17.5 27.5 35.0 40.0 2.5 42.5 72.5 80.0 55.0
Atplus 411F 31.2 60.0 55.0 55.0 25.0 10.0 50.0 82.5 82.5 87.0
62.5 92.0 82.5 67.5 50.0 60.0 80.0 75.0 100 100
125 92.5 100 70.0 65.0 60.0 77.5 100 86.5 100
250 97.0 91.5 100
EXAMPLE 3
Four further tests were carried out using the methodology of Example 1 using Compound No. 12 of EP-355049 in a 25% EC formulation as follows:
g/l
Compound No. 12 250
Calcium dodecyl benzene sulphonate 12.5
Synperonic NP13 12.5
Solvesso 150 to 1 litre
The results are set out in Tables III-VI.
TABLE III
PERCENT WEED CONTROL 19 DAYS AFTER TREATMENT
EH PI TM CA ST EI SH AG DG LL CN
Compound 12 Rate +1.0% g/ha:
Atplus 411F 1.56 36.0 10.3 15.7 7.7 23.7 21.7
3.1 61.0 23.3 24.3 17.7 36.5 33.3 20.0 4.7 31.5 10.0
6.2 76.7 48.7 26.7 43.7 51.7 36.7 35.3 25.0 22.5 21.7
12.5 88.5 65.0 36.7 48.7 75.3 30.0 50.0 34.7 36.0 37.7
25 92.7 78.0 49.3 89.7 98.7 45.0 78.7 54.0 53.5 37.7 42.0
50 98.3 94.7 77.4 76.0 95.0 59.0 91.7 87.3 74.5 73.7 26.7
100 94.3 98.3 65.3 100 99.3 85.0 99.3 34.3
200 100 99.0 38.3
400 55.0
800 98.3
Compound 12 1.5 57.7 13.3 14.7 9.0 24.3 18.3 +1.05 3.1 50.0 21.0 20.0 16.7 49.3 28.7 19.3 7.3 7.5 9.0
Orchex 796 6.2 76.3 45.0 26.7 31.7 74.3 27.3 20.0 26.7 25.0 16.7 & tplus 12.5 88.3 58.7 38.7 45.0 87.0 34.0 50.0 52.3 24.0 24.3 300F 25 96.3 85.0 50.3 77.3 100 36.7 80.0 63.7 62.5 34.3 40.7
50 97.3 92.0 66.7 94.3 59.3 99.0 86.0 68.5 52.7 36.0
100 77.7 91.3 66.7 83.3 98.7 99.0 86.3 31.7
200 100 99.7 45.3
400 54.0
800 82.3
TABLE III (continued)
PERCENT WEED CONTROL 19 DAYS AFTER TREATMENT
EH PI TM CA ST EI SH AG DG LL CN
Compound 12 Rate +1.0% g/ha::
Compound 12 1.5 45.7 5.0 11.7 10.7 18.3 15.0 +1.0% 3.1 58.3 32.7 15.7 6.7 22.7 16.7 12.3 6.0 30.0 6.7
Atplus 412 6.2 84.0 42.3 27.7 17.7 24.3 23.3 15.0 15.0 45.0 13.3 12.5 93.7 49.0 27.7 41.7 48.3 28.3 23.3 35.0 40.0 14.0
25 97.0 61.0 39.0 47.0 70.0 30.0 48.3 50.7 58.5 16.0 31.0
50 97.3 89.3 63.3 86.0 85.0 35.0 76.3 67.3 72.5 26.0 26.0
100 95.0 85.3 . 57.7 83.3 93.0 78.5 40.3 17.3
200 98.5 73.3 50.0
400 63.0
800 96.3
Compound 12 Rate
g/ha: :
1.5 35.0 11.3 20.3 5.0 18.3 7.7 +0.25% 3.1 72.3 26.7 22.7 8.3 24.3 14.0 13.0 10.0 20.0 6.7
Calsolene 6.2 76.3 44.3 28.3 25.0 36.0 22.7 18.3 23.3 39.0 16.3
Oil HS 12.5 93.0 52.7 48.3 44.7 42.7 23.7 40.3 41.7 49.0 25.0 25 97.0 71.3 61.7 61.7 67.0 36.3 68.3 60.3 59.5 23.3 31.7
50 97.3 81.7 92.0 84.0 87.7 44.3 77.7 73.0 68.5 46.0 32.0
100 100 94.3 52.3 86.3 99.0 80.0 68.7 44.3
200 80.0 73.0 28.3
400 55.7
800 83.3
Compound 12 1.5 44.3 16.7 18.3 9.3 26.0 9.3 +0.25% 3.1 57.7 38.7 22.7 20.0 33.3 21.7 15.0 15.0 33.5 11.7
Q2 5152 6.2 74.3 58.3 40.3 34.3 39.7 25.0 25.0 35.0 35.0 12.3
12.5 92.3 75.0 35.0 57.0 59.3 32.3 37.3 51.7 36.0 32.7
25 93.7 85.7 65.3 70.0 71.3 42.3 53.3 65.7 57.0 48.0 32.7
50 97.0 92.3 80.3 81.0 81.7 48.3 64.0 98.0 63.0 62.0 40.0
100 100 100 62.0 97.0 99.7 70.5 96.7 45.0
200 93.0 99.3 52.3
400 49.3
800 86.0
TABLE III (continued)
PERCENT WEED CONTROL 19 DAYS AFTER TREATMENT
EH PI TM CA ST EI SH AG DG LL CN
Compound 12 Rate +1.0% g/ha:
Compound 12 1.5 33.3 21.7 21.7 16.7 20.0 19.0 +0.25% 3.1 52.7 34.3 34.3 31.0 29.3 24.3 17.3 15.0 27.5 16.0 X25309 6.2 68.0 44.3 44.3 35.0 37.721.020.7 27.0 37.5 17.0
12.5 89.7 74.7 74.7 55.7 41.7 37.7 23.7 32.7 45.0 21.0
25 95.0 98.0 98.0 86.3 72.0 45.0 41.0 63.0 59.5 25.0 31.7
50 97.0 93.0 93.0 85.3 81.3 42.0 54.3 87.3 72.0 66.7 53.0
100 98.7 56.0 83.3 99.3 88.5 73.0 50.0
200 87.5 99.0 35.0
400 49.3
800 84.3
TABLE IV
PERCENT WEED CONTROL 19 DAYS AFTER TREATMENT
EH PI TM CA ST EI SH AG DG LL CN
Compound 12 1.5 64.7 31.7 35.3 30.0 21.0 + 1.0% 3.1 92.7 54.7 36.0 50.0 61.0 36.7 33.3 29.0
Atplus 411F 6.2 91.0 71.0 43.3 85.0 83.3 38.7 67.0 30.0 29.3
12.5 93.3 94.0 65.0 51.7 91.0 100 79.0 71.7 47.7 52.3
25 93.7 90.3 91.7 57.0 95.3 92.3 94.0 92.7 95.0 61.0 34.3
50 95.0 98.0 94.3 73.3 97.3 99.7 99.3 98.3 91.7 87.0 37.7
100 97.0 83.3 98.7 99.0 96.7 36.7
200 97.7 98.7 52.7
400 96.7 75.3
800 90.7
TABLE IV (continued)
PERCENT WEED CONTROL 19 DAYS AFTER TREATMENT
EH PI TM CA ST EI SH AG DG LL CN
Compound 12 1.5 66.7 23.3 35.0 30.0 23.3 + 1.0% 3.1 86.7 37.7 26.7 41.0 49.0 26.7 44.3 17.3
Canplus 6.2 92.0 80.3 39.0 69.0 66.7 50.0 55.0 31.7 12.3
12.5 93.7 95.3 64.3 68.3 89.3 64.7 72.0 70.7 50.7 41.7
25 93.0 97.7 82.7 56.7 95.7 85.7 97.3 83.3 73.0 44.0 21.0
50 95.0 99.3 92.3 74.3 97.0 98.7 97.3 90.3 89.0 68.7 32.0
100 94.7 79.7 98.0 99.0 87.0 29.3
200 98.0 98.7 57.0
400 99.0 73.3
800 98.3
Compound 12 1.5 66.7 13.0 26.7 19.0 13.0 + 1.0% 3.1 77.3 29.3 28.3 26.7 28.7 20.7 22.3 6.7
Spraymate 6.2 91.0 53.7 40.0 44.3 52.7 30.0 22.0 22.3 15.7
L1700 12.5 93.0 74.0 65.0 45.3 61.0 78.7 56.7 54.3 36.0 22.7
25 93.7 87.7 68.3 47.7 76.7 81.7 76.3 65.7 41.0 27.0 14.7
50 94.3 99.3 90.0 55.0 90.0 96.0 98.7 90.7 41.7 38.7 20.0
100 95.3 62.0 96.7 79.0 59.0 33.3
200 71.3 76.0 40.0
400 77.7 53.3
800 71.0
Compound 12 1.5 66.7 11.7 16.7 23.3 18.3 +0.25% 3.1 75.0 33.3 18.3 25.0 40.3 26.0 30.3 6.7
Acer 6.2 83.3 55.3 39.3 43.3 40.0 50.0 52.7 15.0 17.7 89002 12.5 86.0 79.0 59.7 38.3 51.0 77.7 68.0 65.0 41.0 23.3
25 92.7 94.0 76.7 53.3 84.0 80.3 85.0 78.7 53.0 38.3 22.7
50 92.7 98.3 84.0 73.3 89.7 88.7 81.7 94.0 71.7 54.7 29.3
100 89.0 76.3 97.3 90.7 67.3 30.3
200 82.0 67.0 60.0
400 83.3 68.3
800 88.3
TABLE V
PERCENT WEED CONTROL 13 DAYS AFTER TREATMENT GA SM PI CA AG AV LL EI DG ST
Compound 12 3.9 81.7 77.3 23.3 26.7
+ 1.0% 7.8 91.0 91.3 45.0 43.3 21.7
Atplus 411F 15.6 98.7 99.0 84.0 41.7 50.0 30.0 55.0 85.0 65.0 65.0
31.2 98.7 99.0 84.0 61.7 76.7 79.3 85.0 98.3 70.0 82.0
62.5 77.7 91.0 94.3 98.3 71.7 95.7
125 79.3 98.3 99.0 93.3 99.0
Compound 12 3.9 71.7 81.3 50.0 33.3 + 0.25% 7.8 75.0 97.7 56.7 48.3 35.0
Synprolam 15.6 90.7 99.3 58.3 70.0 56.7 51.7 45.0 74.3 51.7 45.0 35x10 31.2 98.0 99.3 89.0 63.3 68.3 75.0 53.3 80.7 53.3 51.7
62.5 77.7 99.3 83.3 91.0 66.7 66.7
125 80.7 86.0 97.7 75.0 86.0
Compound 12 3.9 56.7 97.3 33.3 28.3 + 0.25% 7.8 73.3 99.0 56.7 38.3 35.0
Synperonic 15.6 98.3 99.0 70.0 53.3 51.7 35.0 48.3 58.3 50.0 36.7
A20 31.2 98.3 99.0 85.7 68.3 61.7 65.0 58.3 71.7 56.7 53.3
62.5 72.3 89.7 65.0 89.0 70.0 68.3
125 85.0 81.7 96.0 73.3 79.0
Compound 12 3.9 58.3 99.0 43.3 31.7 + 0.25% 7.8 91.3 99.0 71.7 40.0 36.7 Silwet L77 15.6 98.0 99.0 87.7 51.7 48.3 66.7 61.7 69.0 55.0 43.3
31.2 98.3 99.0 92.3 65.0 58.3 89.0 55.0 83.7 58.3 56.7
62.5 81.7 92.7 85.0 97.3 63.3 58.3
125 81.7 94.3 98.7 75.0 85.6
TABLE VI
PERCENT WEED CONTROL 14 DAYS AFTER TREATMENT GA IH PI CA AG AV LL EI DB ST
Compound 12 3.9 61.7 92.5 41.7 + 1.0% 7.8 79.0 75.0 65.0 31.7 43.3 21.7
Atplus 15.6 77.0 96.5 82.3 30.0 65.0 55.0 45.0 411F 31.2 98.3 95.5 95.7 63.3 91.7 69.3 79.0 73.3 79.0 84.7
62.5 73.3 96.7 100 91.0 87.3 94.3 88.7
125 99.3 97.7 100 99.0
250 97.0 97.7 99.0
Compound 12 3.9 67.7 71.5 63.3 + 0.25 7.8 84.0 77.5 58.3 36.7 45.0 33.3
Synperonic 15.6 90.0 97.5 88.0 51.7 51.7 45.0 30.0
A7 31.2 98.7 96.5 99.0 78.3 89.3 91.3 62.7 79.3 68.3 76.3
62.5 73.3 97.3 98.0 93.7 82.3 76.7 84.0
125 98.3 85.7 88.3 92.0
250 98.3 98.3 98.3
Compound 12 3.9 70.0 70.0 45.0 + 0.25% 7.8 80.7 86.5 71.7 63.3 33.3 45.0
Synperonic 15.6 91.0 95.0 91.0 56.7 75.3 65.0 36.7 91 31.2 83.3 97.5 86.7 60.0 81.3 81.3 43.3 74.0 79.7 59.0
62.5 70.7 98.0 99.3 78.3 77.0 68.3 87.7
125 99.0 91.0 89.3 94.3
250 98.7 97.3 98.7
Compound 12 3.9 64.3 72.5 53.3 + 0.25% 7.8 63.3 57.5 50.0 26.7 35.0 23.3
Tween 20 15.6 76.0 67.5 71.0 31.7 26.7 51.7 25.0 31.2 88.7 95.0 82.7 58.3 60.0 53.3 28.3 43.3 75.0 55.0
62.5 63.3 55.0 69.3 46.7 60.7 81.7 60.0
125 82.3 68.3 81.3 84.7
250 72.3 95.3 97.0
TABLE VI (continued)
PERCENT WEED CONTROL 14 DAYS AFTER TREATMENT GA IH PI CA AG AV LL EI DB ST
Compound 12 3.9 77.7 77.5 71.0 + 0.25% 7.8 81.3 87.5 70.0 31.7 26.7 35.0
HD373 15.6 99.0 75.0 90.0 45.0 71.7 67.7 33.3
31.2 99.0 100 98.7 60.0 92.3 90.0 58.3 65.7 72.3 74.7
62.5 53.3 92.7 99.0 56.7 88.0 87.0 84.0
125 99.7 93.0 87.0 99.0
250 98.0 98.3 98.7
Compound 12 3.9 73.7 75.0 45.0 + 0.25% 7.8 89.3 91.0 77.0 35.0 40.0 25.0
Abil 15.6 97.7 92.5 85.7 35.0 58.3 61.0 51.7
ZP2434 31.2 98.7 95.0 94.7 61.7 85.7 85.0 68.0 76.3 80.3 65.0
62.5 62.7 98.3 95.0 83.0 85.7 81.3 78.0
125 99.7 81.3 90.0 95.0
250 97.3 97.7 99.0
EXAMPLE 4
Two further tests were carried out using the methodology of Example 1 using the methyl ester of Compound No. 15 of EP-355049 in a 7.5% EC formulation as follows: :
g/l
Methyl ester of Compound No. 15 75
Calcium dodecyl benzene sulphonate 50
Synperonic NP13 50
Solvesso 150 to 1 litre
The results are set out in Table VII and VIII.
TABLE VII
PERCENT WEED CONTROL 17 DAYS AFTER TREATMENT
Methyl ester of
COMPOUND 15 RATE CA EH TM ECA SH ST AG EI DG LL CN
+1.0% g/ha
ATPLUS 411F 1.5 20.0 50.0 26.0 5.0 46.0
3.1 33.7 70.0 62.3 16.7 63.7 21.7 26.7 33.3 10.0
6.2 53.7 71.7 70.0 35.0 77.0 79.3 23.3 52.0 35.3 11.7
12.5 67.0 87.7 76.7 40.0 47.0 84.7 38.7 70.3 56.7 16.7
25 91.3 95.0 100 73.3 100 98.0 69.0 81.7 73.7 37.0 11.7
50 96.0 95.0 100 73.3 100 99.3 86.7 97.3 95.0 77.7 13.3
100 96.3 96.0 100 99.3 100 100 98.3 96.3 100 92.7 32.7
200 100 99.0 99.3 100 99.0 31.0
Methyl ester of
COMPOUND 15 1.5 61.3 68.3 26.7 8.3 35.0 +1.0% 3.1 46.7 51.7 60.7 13.3 51.7 20.0 21.0 30.0 16.7
AL2042 6.2 58.7 89.3 69.0 26.7 29.3 61.7 27.0 30.0 32.7 18.3
12.5 80.3 95.0 86.7 25.0 70.3 76.7 31.7 41.0 38.7 21.0
25 86.7 95.0 100 47.7 91.7 91.0 50.0 46.7 62.0 27.7 6.7
50 96.3 96.0 100 66.7 100 98.0 66.0 66.0 72.0 53.3 8.3
100 98.7 95.0 100 80.0 100 99.7 93.0 82.0 100 57.0 21.7
200 90.0 95.3 93.3 100 73.7 40.0
Methyl ester of
COMPOUND 15 1.5 24.3 51.7 31.7 8.3 50.0 + 1.0% 3.1 43.7 58.3 57.0 20.0 49.3 24.3 40.0 26.0 11.7
AZONE 6.2 60.0 66.7 63.7 19.3 40.3 50.0 21.7 37.7 38.3 21.7
12.5 67.0 83.3 83.3 26.7 42.0 53.7 46.7 46.7 48.3 20.0
25 80.0 93.3 100 51.7 67.3 75.3 50.0 69.0 62.3 30.3 13.3
50 90.0 88.3 100 55.0 78.3 89.7 70.7 71.7 60.0 50.0 21.7
100 95.0 95.0 100 81.7 95.0 92.3 91.0 98.7 69.0 93.0 36.0
200 98.3 99.0 99.0 86.7 99.0 51.7
TABLE VII (continued)
PERCENT WEED CONTROL 17 DAYS AFTER TREATMENT
Methyl ester of
COMPOUND 15 RATE CA EH TM ECA SH ST AG EI DG LL CN
+1.0% g/ha
Methyl ester of
COMPOUND 15 1.5 31.7 61.7 36.0 10.0 32.7 + 1.0% 3.1 51.0 61.7 69.0 22.7 53.3 15.0 31.0 27.7 11.7
ORCHEX 796 6.2 57.3 78.3 83.7 26.7 43.3 81.7 25.0 63.7 38.7 15.0 + ATPLUS 12.5 82.0 91.7 81.7 41.7 91.7 86.7 49.7 70.3 46.0 24.3 300F 25 88.3 95.0 98.3 86.7 100 99.3 77.0 88.3 73.7 35.0 20.0
50 97.7 95.0 100 88.3 100 99.7 94.3 98.0 91.7 62.0 28.3
100 96.0 95.0 100 100 100 100 99.0 97.7 100 87.0 33.3
200 99.7 99.0 99.0 100 98.0 32.7
Methyl ester of
COMPOUND 15 1.5 27.7 76.7 52.0 27.7 50.0 + 1.0% DASH 3.1 50.3 83.3 70.7 36.7 48.3 24.3 38.3 33.7 10.0
6.2 46.7 92.7 81.7 30.0 63.3 76.7 38.7 60.7 50.0 20.0
12.5 83.7 95.0 95.0 53.3 91.7 90.7 45.0 70.5 58.7 21.7
25 88.3 94.3 100 89.7 100 99.3 78.3 68.7 72.3 50.0 15.0
50 88.3 95.0 100 84.7 100 99.7 88.0 96.7 88.3 58.7 15.0
100 97.3 96.0 100 99.7 100 100 99.0 98.7 100 89.3 26.0
200 99.3 99.0 98.0 100 99.0 43.3
Methyl ester of
COMPOUND 15 1.5 36.0 89.3 100 38.3 56.7 + 1.0% DASH 3.1 27.7 80.0 69.0 51.3 57.0 16.7 36.0 30.3 18.3 + 4.02 urea 6.2 51.7 90.7 75.3 43.3 88.7 68.7 36.0 62.0 45.0 23.3 ammonium 12.5 86.7 91.7 93.3 49.7 80.3 81.7 51.3 70.3 63.7 26.0 nitrate 25 89.3 95.0 98.3 81.7 99.7 94.7 75.7 84.7 83.3 50.0 11.7
50 96.3 96.0 100 95.0 99.7 99.3 89.7 96.3 100 68.3 15.0
100 99.0 96.0 100 99.7 99.7 99.7 98.7 98.0 100 99.0 30.0
200 100 99.0 98.3 100 99.0 38.3
TABLE VIII
PERCENT WEED CONTROL 17 DAYS AFTER TREATMENT
Methyl ester of
COMPOUND 15 RATE TM EH ST SH CA EI LL AG DG ECA CN
+1.0% g/ha
ATPLUS 1.5 33.3 44.3 51.7 15.7 46.7 35.0
411F 3.1 54.3 54.3 67.3 52.3 75.0 70.3 35.0 47.0
6.2 73.3 85.0 86.3 69.3 82.0 79.3 39.3 66.0 63.3
12.5 94.3 93.3 96.7 78.3 93.3 97.7 53.0 33.3 78.3 82.3
25 100 95.7 100 93.3 96.3 99.0 77.7 56.7 83.3 89.0 52.0
50 100 95.7 100 99.3 99.0 97.3 82.7 100 100 45.0
100 100 96.3 100 99.7 99.0 100 100 45.0
200 98.7 100 62.0
Methyl ester of
COMPOUND 15 1.5 47.3 47.0 40.3 21.7 48.7 40.0 + 0.25% 3.1 77.7 60.0 63.3 29.3 75.0 52.7 25.0 53.3
SILWET L77 6.2 90.7 71.7 73.3 50.3 86.7 80.0 31.0 70.0 73.3
12.5 98.3 85.0 80.0 74.0 92.7 99.0 43.3 27.3 85.3 74.0
25 100 93.7 97.3 90.7 98.7 99.7 68.0 57.7 99.7 82.7 69.0
Methyl ester of
COMPOUND 15 1.5 41.7 40.0 36.0 20.7 36.0 31.7 + 0.25% 3.1 60.7 60.0 52.0 37.7 75.0 54.7 14.7 50.0
X2 5309 6.2 80.3 70.0 67.3 62.3 91.7 80.0 34.3 62.3 61.7
12.5 100 83.3 80.7 73.7 97.3 83.7 53.0 15.7 76.7 71.7
25 100 92.3 94.3 93.3 97.7 99.3 53.7 23.3 90.7 78.0 66.0
Methyl ester of
COMPOUND 15 1.5 32.3 73.3 42.7 29.0 40.0 48.3 + 0.25% 3.1 75.0 75.3 49.7 27.0 76.7 71.7 30.0 48.3
HD373 6.2 82.0 81.7 75.0 65.3 85.3 85.7 27.3 77.3 57.7
12.5 98.7 91.7 94.0 94.7 98.0 97.7 37.7 31.0 75.3 65.3
25 100 94.0 99.7 87.7 98.7 66.7 38.3 89.7 79.7 70.7
TABLE VIII (Continued)
PERCENT WEED CONTROL 17 DAYS AFTER TREATMENT
RATE TM EH ST SH CAL EI LL AG DG ECA CN
Methyl ester of
COMPOUND 15 1.5 44.3 71.7 56.7 24.0 51.7 46.0 + 0.25% 3.1 61.0 78.3 60.3 51.7 81.7 64.0 14.7 62.3
SYNPERONIC 6.2 75.7 85.0 73.7 58.3 88.7 76.7 40.7 70.3 65.3
A7 12.5 98.7 92.3 91.0 90.0 97.7 94.3 42.0 20.7 86.7 70.3
25 100 94.0 97.7 99.7 98.7 99.0 61.0 52.3 90.7 75.0 58.7
Methyl ester of
COMPOUND 15 1.5 25.0 63.3 52.0 26.7 58.7 41.7 + 0.25% 3.1 57.0 67.3 60.0 46.7 78.7 62.0 7.3 60.3
Synperonic 6.2 87.0 75.0 80.0 41.0 76.7 69.7 32.7 65.0 65.0
A20 12.5 95.0 89.0 87.7 77.0 85.7 90.7 40.7 18.0 82.7 67.0
25 100 89.0 98.3 84.3 96.0 96.7 64.7 33.3 85.0 70.0 53.7
TABLE IX
Abbreviations used for Test Plants
Ih - Ipomoea hederacea
Pi - Polygonum aviculare
Ca - Chenopodium album Ga - Gallium aparine
Eh - Euphorbia heterophylla
Av - Avena fatua
Dg - Digitaria sanguinalis
St - Setaria viridis
Sh - Sorghum halepense
Ag - Agropyron repens
Cn - Cyperus rotundus
Ei - Eleusine indica
Ll - Lolium penenne
Oo - Ottochloa nodosa
Sm - Stellaria media
Tm - Matricaria perforata
Eca - Conyza canadensis
Claims (29)
- CLAIMS 1. A herbicidal composition comprising a compound as defined in EP-A-355049 or EP-A-367242 in combination with an adjuvant selected from silicon polymers, oil based spray adjuvants, alcohol ethoxylates, nonyl phenol ethoxylates, amine ethoxylates, blended surfactants and alkoxylated amines.
- 2. A herbicidal composition according to claim 1 in which the adjuvant is selected from Silwet L77 , Q2 5152, X2 5309, Abil ZP2434, Atplus 411F, Atplus 412, Complus 328, Spraymate, Orchex 796, Atlox 4848, Synperonic A7, Synperonic 91/6, Synperonic A20, Agral 90, Synprolam 35x10, Ethoquad C15, Atplus 300F, Acer 89001 and Acer 89002.
- 3. A herbicidal composition according to claim 2 in which the adjuvant is Silwet L77.
- 4. A herbicidal composition according to claim 2 in which the adjuvant is Q2 5152.
- 5. A herbicidal composition according to claim 2 in which the adjuvant is X2 5309.
- 6. A herbicidal composition according to claim 2 in which the adjuvant is Abil ZP2434.
- 7. A herbicidal composition according to claim 2 in which the adjuvant is Atplus 411F.
- 8. A herbicidal composition according to claim 2 in which the adjuvant is Atplus 412.
- 9. A herbicidal composition according to claim 2 in which the adjuvant is Complus 328.
- 10. A herbicidal composition according to claim 2 in which the adjuvant is Spraymate.
- 11. A herbicidal composition according to claim 2 in which the adjuvant is Orchex 796.
- 12. A herbicidal composition according to claim 2 in which the adjuvant is Atlox 4848.
- 13. A herbicidal composition according to claim 2 in which the adjuvant is Synperonic A7.
- 14. A herbicidal composition according to claim 2 in which the adjuvant is Synperonic 91/6.
- 15. A herbicidal composition according to claim 2 in which the adjuvant is Synperonic A20.
- 16. A herbicidal composition according to claim 2 in which the adjuvant is Agral 90.
- 17. A herbicidal composition according to claim 2 in which the adjuvant is Synprolam 35x10.
- 18. A herbicidal composition according to claim 2 in which the adjuvant is Ethoquad C15.
- 19. A herbicidal composition according to claim 2 in which the adjuvant is Atplus 300F.
- 20. A herbicidal composition according to claim 2 in which the adjuvant is Acer 89001.
- 21. A herbicidal composition according to claim 2 in which the adjuvant is Acer 89002.
- 22. A herbicidal composition comprising a compound as defined in EP-A-355049 or EP-A-367242 in combination with an adjuvant selected from alkyl glucosides, sulphated oils, urea ammonium nitrate, Azone and DASH.
- 23. A herbicidal composition according to claim 22 in which the adjuvant is an alkyl glucoside.
- 24. A herbicidal composition according to claim 22 in which the adjuvant is a sulphated oil.
- 25. A herbicidal composition according to claim 23 in which the adjuvant is an Calsolene oil HS.
- 26. A herbicidal composition according to claim 22 in which the adjuvant is urea ammonium nitrate.
- 27. A herbicidal composition according to claim 22 in which the adjuvant is Azone.
- 28. A herbicidal composition according to claim 22 in which the adjuvant is DASH.
- 29. A method of killing or controlling unwanted plant species which method comprises applying to the plants or to the locus thereof a herbicidally effective amount of a composition according to any of claims 1 to 28.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919113987A GB9113987D0 (en) | 1991-06-28 | 1991-06-28 | Herbicidal compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9212097D0 GB9212097D0 (en) | 1992-07-22 |
| GB2257044A true GB2257044A (en) | 1993-01-06 |
Family
ID=10697492
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB919113987A Pending GB9113987D0 (en) | 1991-06-28 | 1991-06-28 | Herbicidal compositions |
| GB9212097A Withdrawn GB2257044A (en) | 1991-06-28 | 1992-06-08 | Aryloxy benzotriazole herbicidal compositions |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB919113987A Pending GB9113987D0 (en) | 1991-06-28 | 1991-06-28 | Herbicidal compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB9113987D0 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994023574A1 (en) * | 1993-04-20 | 1994-10-27 | Akzo Nobel N.V. | Activity promoting additives for rest-breaking agents |
| WO1996001049A1 (en) * | 1994-07-05 | 1996-01-18 | Akzo Nobel N.V. | Activity promoting additives for rest-breaking agents |
| US5885932A (en) * | 1995-07-03 | 1999-03-23 | Akzo Nobel N.V. | Activity promoting additives for rest-breaking agents |
| US6093680A (en) * | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| US6130186A (en) * | 1996-10-25 | 2000-10-10 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0257686A1 (en) * | 1986-08-20 | 1988-03-02 | Akzo N.V. | Herbicides and fungicides containing activity promoting additives |
| EP0355049A2 (en) * | 1988-08-18 | 1990-02-21 | Zeneca Limited | Heterocyclic compounds |
| EP0367242A2 (en) * | 1988-11-03 | 1990-05-09 | American Cyanamid Company | Aryloxy benzotriazole herbicidal agents and methods for the preparation thereof |
| EP0444769A1 (en) * | 1990-02-16 | 1991-09-04 | Zeneca Limited | Herbicidal compositions |
-
1991
- 1991-06-28 GB GB919113987A patent/GB9113987D0/en active Pending
-
1992
- 1992-06-08 GB GB9212097A patent/GB2257044A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0257686A1 (en) * | 1986-08-20 | 1988-03-02 | Akzo N.V. | Herbicides and fungicides containing activity promoting additives |
| EP0355049A2 (en) * | 1988-08-18 | 1990-02-21 | Zeneca Limited | Heterocyclic compounds |
| EP0367242A2 (en) * | 1988-11-03 | 1990-05-09 | American Cyanamid Company | Aryloxy benzotriazole herbicidal agents and methods for the preparation thereof |
| EP0444769A1 (en) * | 1990-02-16 | 1991-09-04 | Zeneca Limited | Herbicidal compositions |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994023574A1 (en) * | 1993-04-20 | 1994-10-27 | Akzo Nobel N.V. | Activity promoting additives for rest-breaking agents |
| US5693591A (en) * | 1993-04-20 | 1997-12-02 | Akzo Nobel N.V. | Activity promoting additives for rest-breaking agents |
| WO1996001049A1 (en) * | 1994-07-05 | 1996-01-18 | Akzo Nobel N.V. | Activity promoting additives for rest-breaking agents |
| US5885932A (en) * | 1995-07-03 | 1999-03-23 | Akzo Nobel N.V. | Activity promoting additives for rest-breaking agents |
| US6093680A (en) * | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| US6093681A (en) | 1996-10-25 | 2000-07-25 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| US6130186A (en) * | 1996-10-25 | 2000-10-10 | Monsanto Company | Composition and method for treating plants with exogenous chemicals |
| US6475953B1 (en) | 1996-10-25 | 2002-11-05 | Monsanto Technology Llc | Composition and method for treating plants with exogenous chemicals |
| US6479434B1 (en) | 1996-10-25 | 2002-11-12 | Monsanto Technology Llc | Composition and method for treating plants with exogenous chemicals |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9212097D0 (en) | 1992-07-22 |
| GB9113987D0 (en) | 1991-08-14 |
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Legal Events
| Date | Code | Title | Description |
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| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |