ZA200300762B - Mesotrione formulations. - Google Patents

Mesotrione formulations. Download PDF

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Publication number
ZA200300762B
ZA200300762B ZA200300762A ZA200300762A ZA200300762B ZA 200300762 B ZA200300762 B ZA 200300762B ZA 200300762 A ZA200300762 A ZA 200300762A ZA 200300762 A ZA200300762 A ZA 200300762A ZA 200300762 B ZA200300762 B ZA 200300762B
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South Africa
Prior art keywords
formulation
common
mesotrione
volume
uan
Prior art date
Application number
ZA200300762A
Inventor
Rex Alan Wichert
Thomas Homer Beckett
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Syngenta Participations Ag
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Publication of ZA200300762B publication Critical patent/ZA200300762B/en

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  • Fertilizers (AREA)
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Description

02-10-2002 1010189
MESOTRIONE FORMULATIONS
Mesotrione, (2-[4-methylsulfonyl-2-nitrobenzoyl- 1,3-cyclohexane dione), is a new broadleaf weed herbicide being developed for post emergence and preemergence use in corn. Adjuvants are highly preferred in order to optimise its post emergence activity.
Proc. North. Cent. Weed Sci. Soc., vol 54, 1999, p 9; Abstr. Meet. Weed Sci
Soc. Am., vol 39, 1999, p 65-66; and Proc. North Cent. Weed Sci. Soc., vol. 52, 1997, p 104-105 all disclose the use of herbicidal formulations comprising crop oil concentrate alone or with urea ammonium nitrate fertilizer. -
W00092/19107 discloses a herbicidal cornposition comprising a substituted cyclohexanedione and at least one nitrogen containing fertilizer.
W099/63823 discloses a herbicidal mixture containing a 3-heterocyclyl-substituted benzoyl derivative, a nitrogen containing fertilizer and an adjuvant.
WO95/17094 discloses a herbicidal composition comprising a diphenyl ether , at least one nitrogen containing fertilizer and one or more adjuvants.
Glasshouse and field experiments have been conducted to evalnate weed and crop response to mesotrione applied post emergence with several adjuvant systems. Rates of mesotrione ranged from 50 to 140 g active ingredient (ai) per acre (A). Adjuvant systems tested mclude; (i) no adjuvant (control), (ii) crop oil concentrate (COC), (iii) non-ionic surfactant (NIS), and (iv) methylated seed oil (MSO), each with and without urea ammonium nitrate (UAN) and ammonium sulphate (AMS) fertilizers.
The average crop response to mesotrione applied with crop oil concentrate plus ammonium nitrate or ammonium sulphate at 105 g active ingredient per hectare (ha) is less than 2% with a maximum injury of less than 10% in over 96% of the experiments.
AMENDED SHEET
480022 EPO JS IPER ID:ex_wilmington_lib h\rware_dataupdprothdataiex_wi Page 8
- 02-1 0-2002 1B010188
The use of methylated seed oil with mesotrione increases the potential for crop injury. The average crop response to mesotrione applied with MSO plus UAN or AMS at 105 g active ingredient per hectare (ha) was only 3%, but injury was greater than 15% in more than 15% of the trials. In a scries of trials where broadleaf weed control was challenged by large difficult-to-control weeds, mesotrione applied with COC pls UAN or
AMS and mesotrione applied with MSO plus UAN or AMS gave similar levels of control
Mesotrione applied with NIS plus UAN or AMS tended to give less control than the combinations with COC or MSO. Experiments also show that varying water quality and application volumes have little or no impact on the activity of mesotrione when applied at recommended rates with these adjuvant systems.
Data from these experiments show that in order to optimise weed control and minimize crop response with mesotrione, the preferred adjuvant system is COC plus UAN.
However, if efficacy with acceptable sacrifice in crop damage is the desired result, mesotrione plus MSO and UAN or AMS is the formulation of choice.
Thus, in a first aspect, the present invention provides a herbicidal formulation comprising (A) (2-[4-methylsulfonyl-2-nitrobenzoyl)- 1,3-cyclohexanedione), (B) about 0.3 to about 2.5 percent of crop oil concentrate or about 0.3 to abont 2.5 percent of methylated seed oil, on a volume to volume basis, based on the total of (A), (B), (C) and (D), (C) about 0.5 to about 5% of a urea ammonium nitrate on a volume to volume basis, based on the total of (A), (B), (C) and (D), or about 0.5 to 5 % based on dry weight, of ammonium sulphate fertilizer, based on the total weight of (A), (B), (C) and (D), and (D) a diluent
Preferably, the mesotrione is utilized in an amount of about 1 ounce (28g) to 6 ounces (170g) per acre; the amount utilized per 100 (US) gallons (380 litres) of solution would thus correspond to how many gallons of solution would be applied on a per acre basis. Such amounts would ordinarily vary from about 3 ounces (85g) in 5 gallons (19 I) to about 3 ounces (85g) in 30 gallons (114 I). In a typical formulation, based on a 100
AMENDED SHEET annnnAa COM IC IDTD Mme wnbmiantae Lik kBAncarm dstalindnrndfiAdstaiae ow Pana g
02-10-2002 18010189 gallon (380 I) sample of the formulation, about 3 ounces (85g) of mesotrione will be utilized for post-emergent use, and about 5-6 ounces (142-170g) for preemergent usage.
The term “crop oil concentrate” is a well known term in the herbicide art and denotes mixtures of petroleum oils and non-ionic surfactants, preferably containing at least about 79% by weight of petroleum oil. There are numerous commercially available crop oil concentrate products, including, for example AGRI-DEX, PENETRATOR, and
PENETRATOR PLUS and from Helena Chemical Company, HER-BIMAX from UAP,
ES CROP OIL PLUS from Gromark, and CROP OIL PLUS, from Wilfarm, (83% parafinic oil, 17% emulsifier surfactant). In addition, US Patent No 5,238,604, incorporated herein by reference, describes certain adjuvant systems and crop oil concentrate products.
Preferred amounts of crop oil concentrate are 0.5 to 2%, most preferably about 1 % on a volume to volume basis.
Methylated Seed Oil is also commercially available. Examples include DESTINY from Cenex, methylated seed oil from Loveland, methylated seed oil from Helena
Chemical, METH OIL from Riverside, PERSIST from Precision, SCOIL from Agsco,
SUNDANCE 1I from Rosens, SUNIT-2 from American Cyanamid and SUPERB from
Wilfarm.
In addition, commercial versions of the methylated seed oil are also sold as combinations with either UAN or AMS, for example PERSIST PLUS and PERSIST
EXTRA from Precision (MSO plus UAN) and DYNE-A-PAK, from Helena Chemical (MSO plus UAN).
Preferably, the methylated seed oil is utilized in an amount of about 0.5 to 2.0 percent, on a volume-to-volume basis with the mesotrione, more preferably about 1 percent.
Preferably, about 1 to 3%, more preferably 1 to 2% of urea ammonium nitrate fertilizer is used. Preferably about 0.5% to 2% of ammonium sulphate is used.
The diluent is generally comprised of water. It is also possible to use other additives, for example buffers, to control pH. pH buffer substances are substances known to the person skilled in the art. A pH buffer substance is a mixture of a weak acid with a
AMENDED SHEET
ARNNP? FPO IS IPFR INtax wilminoton lib hirware datalindnrodidatalex wi Pane 10
@® 02-10-2002 IBO10188 virtually completely dissociated sait of this acid and/or a mixture of a weak base with a virtually completely dissociated salt of this base (see, for example, Rompps Chemie
Lexikon (Rompp's Chemical Encyclopedia, 7th edition, volume 5, head word Buffer™),
The pH of the buffer hardly changes on addition of acids or bases.
Preferred buifer substances in the preferred pH range from about 4 to about 11 are, for example, buffers which contain the following ions; acetate, phosphate, borate, carbonate, citrate, diethylmalonate, nitrilo-trismethylenephosphate. Zwitterionic buffers, such as, for exampk, glycine buffer or 2-(N-morpholino) ethanesulfonic acid (MES) are also suitable. The buffer used generally depends on the pH range, for example phthalate is typically used at a pH range of about 3 to about 4, acetate is typically used at a pH range of about 4 to about 5.5, phosphate is typically used at a pH range of about 5.5 to about 7.5, and carbonate is typically used at a pH range of about 9 to about 10. A pH buffer acetate system is employed in concentrations such that the concentration in the forrmlation is about 0.1 to about 0.3 mol/l, preferentially about 0.15 to about 0.25 mol/l. A pH- buffering acetate system is actually built in the *“Mesotrione/Acetochlor Premix’ formulation at the specified molar ranges. For each buffer system the molar range is different and system specific, however, based on the buffering strength at the working pH range.
Further examples of commercially available buffer agents and adjuvants inchide, but are not limited to BUFFER PS from Helena, which includes alkyl-p- arylpolyethoxyethano} phosphates and organic phosphoric acid, typically utilized at a concentration of about 0.5 to about 4 pt (about 0.24 to 1.9 I) per 100gal (380 I), BUFFER
EXTRA STRENGTH from Helena, which includes a blend of alkylarylpolyethoxyethanol phosphates and organic phosphoric acids, typically utilized at a concentration of about 4 oz to about 2 pt (about 0.095 to 0.95 I) per 100 gal (380 1), BUFFERCIDE from Custom
Chemicals, which includes phosphoric acid, typically utilized at a concentration of about 1 to about 2 pt (about 0.47 to 0.95 I) per 100 gal (380 I), AERODYNE and PENETRATOR
PLUS.
The formulations can be applied via the air or ground using known techniques, typically 5-30 gallons (19 — 1141) per acre (0.4 ha) by ground or 1-5 gallons (3.8 - 191) per acre (0.4 ha) by air.
AMENDED SHEET
02-1 0-2002 IBO1018¢
The amounts and proportions of components (B) and (C) above are preferred embodiments. It is contemplated that a range of about 0.1 to 1.0 % could be utilized in each case.
In a further aspect of the invention, there is provided a method for controlling the 5 growth of undesirable vegetation such as weeds around the locus of a desired plant species such as corn, which comprises applying the above formulations to the focus of such vegetation. Examples of undesired vegetation are velvetleaf, redroot pigweed, common water hemp, Palmer amaranth, ivyleaf moming-giory, prickly sida, giant ragweed, common ragweed, common cocklebur, Eastern black nightshade, common lambsquarters, Pennsylvania smartweed, common sunflower, jimsonweed, hemp sesbania, toothed spurge, common purslane, large crabgrass, yellow foxtail and kochia.
EXAMPLES
A series of trials was conducted to evaluate the effect or adjuvants on control of broadleaf weeds with mesotrione. This series included trials on planted weeds and indigenous weeds. Each trial was designed as a randomised complete block with 3 or more replications. Mesotrione was applied at 0.094 Ib ai/A (105g/ha, 3 02/A, ) with MSO and
COC at 1% v/v with and without UAN at 1 to 2.5% v/v and AMS ar 8.510/100 gallons (about 1%) spray solution. Thirteen trials were conducted in 1999 in which 38 evaluations were made on broadleaved weeds including velvetleaf, redroot pigweed, common water hemp, Palmer amaranth, ivyleaf morning-glory, prickly sida, giant ragweed, common ragweed, common cocklebur, Eastern black nightshade, common lambsquarters,
Pennsylvania smartweed, common sunflower, jimsonweed, hemp sesbania, toothed spurge, common purslane and kochia. The high levels of control observed with all treatments in 20 out of 38 of these datasets tends to mask adjuvant effects (see Table 1).
Tablel
Effect of adjuvants on broadleaf weed control with mesotrione
TRIAL DATA: H-99-US77-52 “All” Broadleaves, 14-36 DAA, 38 datasets
Mean #>90%
Weed Control % Consistenc
Mesotrione 0.094 Ib + MSO [73 fo]
Mesotrione 0.094b+MSO+UAN 1% |78 [21
AMENDED SHEET
480022 EPO JS IPER ID:ex_wilmington_lib h:rware_data\ipdprocidatalex_wi Page 12
. 02-10-2002 IB01018S
Mesotrion 0.094 b+ MSO +UAN2.5% [79 [23
Mesotrione 0.094 Ib + MSO + AMS EI FF
Mesotrione 0.094 Ib + COC 7s Jz
Mesotrione 0.094b+COC+UAN 1% [78 T19 |]
Mesotrione 0.0941b + COC+UAN 2.5% [77 [21
Mesotrione 0.094 Ib + COC + AMS [7s Jao
Mesotrione 0.094 Ib + UAN 1% EX FF
Mesotrione 0.094 Ib + UAN 2.5% EE FE
Mesotriope-0.094 Ib + AMS [60 ~~ Ji9
All herbicide rates are in pounds of active ingredient per acre (Ib aA). 0.094 IVA is about 105 g/ha
Adjuvant rates are 1% MSO, 1% COC, 1 and 2.5% UAN and 8.5 I/100 gal (zbout 1%) : AMS.
The best demonstration of potential adjuvant effects is to concentrate on trials that were conducted under conditions which were not favourable for herbicidal activity or on - weeds which are difficult to control with mesotrione applied alone. Mesotrione applied with the combination Of COC or MSO plus UAN or AMS gave significantly better weed
Control than when applied with just COC or MSO (See Table 2).
Adjuvants also impact com injury. This is best demonstrated by looking at the frequency of injury observed across a large number of field trials conducted between 1996 and 1999. These trials were all designed as randomised complete blocks with at least 3 replications. Mesotrione was applied at 0.094 Ib ai/A (105g ai/ha) (3 02/A) plus 1% viv
COC or MSO with and without UAN at 2.5% v/v or AMS at 8 to 17 1b/100 gallons (about 12%). Combinations of COC plus UAN or AMS result in fewer occurrences of crop injury than MSO plus UAN or AMS (See Table 3).
TABLE 2
Effect of adjuvants from selected trials (adverse conditions (OH) and Difficult-to-control species (AMBEL and AMBTR))
TRIAL DATA; H-99-US77-52 *OH WI
Average
Velvetleaf | Common | Common | Giant Giant
ABUTH | Ragweed | Ragweed | Ragweed { Ragweed
AMBEL | AMBEL | AMBTR | AMBTR [ER EN ER DE EE DE
AMENDED SHEET
480022 EPO JS IPER ID:ex wilmington lib hi\rware dataindprodidata‘ex wi Page 13
-02-10-2002 18010189 28 DAA | 28DAA |32DAA {28DAA | 28DAA 6-8 leaf, 12-14 8-9 leaf, | 5 leaf, 2- | 9-10 8-10” leaf, 8-9” 6” Jeaf, 5.5-7 8-11"
I EE A A
Mesotrione 0.094 Ib | 27 88 ’ + MSO i al + MSO +UAN 1%
Mesotrione 0.094 bb + MSO + UAN 2.5% ld A wl + MSO + AMS = ad A A + COC id A A A lO + COC + UAN 1%
Mesotrione 0.094 Ib 79 + COC + UAN 2.5% od Gl + COC + AMS irl lL + UAN 1%
Fd lA + UAN 2.5% or] ll A + AMS 5% LSDs 9 fw fiz 13 ji *Drought conditions
All herbicide rates in pounds of active ingredient per acre (Ibai/A).
Adjuvant rates are 1% MSO, 1% COC, 1 and 2.5% UAN and 8.5 16/100 gallon (about 1%) AMS
TABLE 3
Effect of Adjuvant on Frequency of Corn Injury using 0.094 Ib al/A (105g/ha) mesotrione with various adjuvants
Frequency Distribution (% of trials in each range)
Maximum Injury Observed (as %)
AMENDED SHEET
480022 EPO JS IPER ID:ex_wilmington lib h:\rware data\ipdorodidata\ex wi Page 14
02-1 0.2002 1B010189
Adjuvant mean #trials <5 5-10 I 10-15 15-20 20-25 25-30 | >30 coci%_Jo6 Jeo Jog [2 Jo Jo Jo jo Jo
COC1%+ |18 BB
UAN 2.5%
AMS
IMsO1%_ [06 [29 foo Jo fo Jo Jo Jo fo |]
Erol al i a a SS
UAN 2.5% rial itll iad lll A KN GO A A
AMS
Examples of Preferred formulations based on 100 gallons (379 I) of formulated solution
Typical 1 8 acre (0.4 ha icati 5s L (A) 30 ounces (1kg) of (2-[4-methylsulfonyl-2-nitrobenzoyl}-1,3- cyclohexanedione), (B) 1 gallon (3.8 I) of crop oil concentrate, (C) 1.5 gallons (5.7 1) of urea ammonium nitrate, and {D) the balance water 2 (A) 30 ounces (1Kg) of (2-[4-methylsulfonyl-2-nitrobenzoyl]-1,3- cyclohexanedione), (B) 1 gallon (3.8 1) of methylated seed oil, (C) 17 Ibs (7.7 Kg) of ammonium sulphate fertilizer, and (D) the balance water 3. (A) 30 ounces (1kg) of (2-[4-methylsulfonyl-2-nitrobenzoyl}-1,3- cyclohexanedione), (B) 1 gallon (3.8 I) of crop oil concentrate, (C) 1.5 gallons (5.7 1) of urea ammonium nitrate, and (D) the balance water
AMENDED SHEET
ARNO EPO IS IPFR IN-ay wilminatan lib hinware datalindnrodiniataey wi Paae 15

Claims (11)

: 02-10-2002 1B010189 WE CLAIM
1. A herbicidal formulation comprising (A) (2-[4-methylsulfonyl-2-nitrobenzoyl]-1,3-cyclohexanedione); (B) about 0.3 to about 2.5 percent of crop oil concentrate, or about 0.3 to about
2.5 percent of methylated seed oil, on a volume to volume basis, based on the total of (A), (B); (C) and (D), (C) about 0 5 to about 5% of a urea ammonium nitrate on a volume to volume basis, based on the total of (A), (B), (C) and (D), or about 0.5 to 5% based on dry weight, of ammonium sulphate fertilizer, based on the total weight of (A), 3), (C) and (D), and (D) a diluent 2 The formulation of claim 1, comprising about 0.5 to 2.0 % crop oil concentrate. .
3. The formulation of claim 1, comprising about 1 % crop oil concentrate.
4. The formulation of claim 1, comprising about 0.5 to 2.0% methylated seed oil.
5. The formulation of claim 1, comprising about 1% methylated seed oil.
6. The formulation of claim 1, comprising about 1 to 3% urea ammonium nitrate
7. The formulation of claim 1, comprising about 0.5 to 2 % ammonium sulphate fertilizer.
8. A herbicidal formulation, on the basis of a 100 gallon solution, comprising (A) about 30 ounces of (2-[4-methylsulfonyl-2-nitrobenzoyl]-1,3- cyclohexanedione), (B) about 1 gallon of crop oil concentrate or 1 gallon of methylated seed oil or a blend thereof, (C) about 1.5 gallons of a urea ammonium nitrate on a volume 10 volume basis or about 17 1bs of ammonium sulphate fertilizer, and AMENDED SHEET 480092 FPO IS IPFR INex wilminaton lib h\rware datalindorodhdatalex wi . Page 16
02-10-2002 IB010188 (D) the balance water.
9. A method for controlling the growth of undesired vegetation around the locus of a desired plant, which comprises applying the formulation of claim 1 to the locus of said vegetation.
10. The method of claim 9 in which the desired plant is corn.
11. The method of claim 10, wherein said undesired vegetation is selected form the group comprising velvetieaf, redroot pigweed, common waterhemp, Palmer amaranth, ivyleaf morningglory, prickly sida, giant ragweed, common ragweed, common cocklebur, Eastern black nightshade, common lambsquarters, Pennsylvania smartweed, common sunflower, jimsonweed, hemp sesbania, toothed spurge, common puslane, large crabgrass, yellow foxtail and Kochia. AMENDED SHEET 480022 EPO JS IPER ID:ex_wilmington_lib h:srware datavipdprodidataiex wi Pao 17
ZA200300762A 2000-09-08 2003-01-28 Mesotrione formulations. ZA200300762B (en)

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