MXPA98000446A - Sarcosinates as adjuvants and activators of fluazifop-but - Google Patents

Sarcosinates as adjuvants and activators of fluazifop-but

Info

Publication number
MXPA98000446A
MXPA98000446A MXPA/A/1998/000446A MX9800446A MXPA98000446A MX PA98000446 A MXPA98000446 A MX PA98000446A MX 9800446 A MX9800446 A MX 9800446A MX PA98000446 A MXPA98000446 A MX PA98000446A
Authority
MX
Mexico
Prior art keywords
sarcosinate
activator
butyl
sodium
herbicidal composition
Prior art date
Application number
MXPA/A/1998/000446A
Other languages
Spanish (es)
Other versions
MX9800446A (en
Inventor
J Crudden Joseph
Original Assignee
Hampshire Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US08/504,273 external-priority patent/US5686391A/en
Application filed by Hampshire Chemical Corp filed Critical Hampshire Chemical Corp
Publication of MXPA98000446A publication Critical patent/MXPA98000446A/en
Publication of MX9800446A publication Critical patent/MX9800446A/en

Links

Abstract

The present invention relates to a Fluazifop-butyl adjuvant, and preferably Fluaziforp-P-butyl, which has increased activity, lower irritation and lower toxicity than conventional adjuvants. The adjuvant is C8 to C22 sarcosinate or sarcosinate salt, such as sodium cocoyl sarcosinate, sodium lauroyl sarcosinate, or combinations thereof, which are combined with Fluazifop-P-butyl and provides more effective activity, control, but all experimental adjuvants gave superior control to that of X-

Description

SARCOSINATES AS ADJUVANTS AND FLUAZIPOP-BUTTER ACTIVATORS BACKGROUND OF THE INVENTION Fluazifop-butyl (butyl (RS) -2- U-L l-5- (trifluor methyl) -2- pyridinium oxij eniloxij propionate), or its enantiomer fluazifop-P-butyl (butyl (R) -2-T4- [C 5- (trifluoromethyl) -2-pyrimidinyl] -oxij = phenoxy = propane) they are represented by the following formula: Both the racemic mixture and the enantiomer are selective herbicides, with the enantiomer being especially effective grass selective herbicide. which exhibits perennial and annual herb grazing post control on top of cotton, soybeans and other broadleaf crops, including asparagus, carrots, dry bulb onions. spinach. sweet potatoes, and ornamental. The ST enantiomer sells comßrcialmßntß by REF: 26496 Zeneca Ag Products under the trade name FUSILADE (R) 2000 or FUSILADE (R) DX. They are typically used in formulations to aid in the operation or improve the effectiveness of the pesticide, herbicide, etc. The term includes wetting agents, dispersants, emulsifiers, dispersing agents, foaming aids, suds suppressors, penetrants and correctors. Adjuvants such as Valent X-77 (R) Spreadßr are commonly used to improve the performance of Fluazifop-P-butyl. However, the Valent X-77 (R) Spreader and other ethoxylated nonionic surfactants contain free ethylene oxide which can form 1,4 dioxane, a known carcinogen. Therefore, an object of the present invention is to provide adjuvants and activators of Fluazifop-P-butyl that do not suffer from the disadvantages of the prior art. A further object of the present invention is to provide herbicidal formulations with increased activity, lower irritation capacity and lower toxicity than conventional formulations.
BRIEF DESCRIPTION OF THE INVENTION The problems of the prior art have been overcome by the present invention, which provides an adjuvant for Fluazifop-butyl, and preferably Fluazifop-P-butyl. which has increased activity, lower irritation and lower toxicity than conventional adjuvants. The adjuvant is C8 sarcosinate a- or sarcosinate salt. such as cocoyl sodium sarcosinate, lauroyl sodium sacosinate, or combinations thereof, which is combined with Fluazifop-P-butyl and provides more effective activity.
DETAILED DESCRIPTION OF THE INVENTION Typically, the sacosinates are used in the form of their sodium, potassium or ammonium salt solution.
The N-acyl sarcosinates produced commercially by the Schotten-Baumann reaction of the sodium salt of sarcosine with the appropriate fatty acid chloride under carefully controlled conditions: R-C-Cl + HNCH2? OONa + NaOH R-C-NOCOCOA + NaCl + H20 J \ - I CH3 0 CH3 wherein R is typically a long chain fatty acid from Cio to Cie. made commonly from lauric, palmitic acid. irish or oleic After the reaction is complete, the crude sodium salt is acidified to release the free fatty acid sarcosinic acid that is separated from the aqueous by-products. Then it is neutralized to a salt form. Sarcosinates such as sodium lauroyl sarcosinate, sodium cocoyl sarcosinate and sodium iristoyl sarcosinate are commercially available under the trademark HAMPOSYL (R) from Hampshire Chemical Corp. as 30% active solutions in water. The present inventor has found that N-acyl sarcosinates from Ce to C22. and in particular, sodium cocoyl sarcosinate and sodium lauroyl sarcosinate, are excellent adjuvants for Fuazifop-P-butyl. (the most (P) enantiomer of Fuazifop-butyl has been found to contain the herbicidal activity of the racemic mixture, in this way it has been isolated and formulated at half the concentration of the racemic mixture. The present invention It should be understood by those skilled in the art, however, that even though the following description refers to the (P) enantiomer, the racemic mixture could also be used.) Sarcosinates are low in toxicity, irritation and when combined with Fuazifop-P-butyl. they cause them to exhibit increased activity. Suitable salts of these sarcosinates which are useful in the present invention include monoethylamine; Diethylamine: triethylamine; alkali metal salts, particularly sodium and potassium; isopropylamine; and ammonia or amino alcohols such as tris amino or 2-dimethylamino-2-methyl-1-propanol. Preferably the salcorsinate solutions at 3036 are used so that the final concentration of sarcosinate in the formulation is from 0.1% to 3% (v / v), more preferably 0.5 to 1%. Higher concentrations of sarcosinate tend to be less effective, probably because the excess of surfactant tends to cause the herbicide to be washed away from the application area. The ST formulations are prepared by first mixing the sarcosinate with water, and then mixing the FUSILADE (R) herbicide with the resulting surfactant solution. The invention is further illustrated by the following non-limiting examples.
EXAMPLE 1 Fuazifop-P-butyl was added to solutions of sodium cocoyl sarcosinate and sodium lauroyl sarcosinate. Valent X-77 was used as control. The Valent X-77 is 90% active and the sarcosinate solutions are 30% active. ST tested four test systems and control for effectiveness in controlling Bermuda grass. The Bermuda grass used in this ST experiment was established in 1985 and has been fertilized and plowed under normal practices until the treatments were applied. Following the application d? the treatments, the unwanted grasses and pastures other than Bressmuda grass with Quadmec were controlled thirty-three days after the application; with MSMA 120 days after treatment, classifications (DAT) were collected. The area was fertilized with 68 units / A of nitrogen 3350 days after the application. The experimental area was irrigated on a base as needed. ST carried out seven and fourteen date classifications. The Fuazifop-P-butyl ST applied Bermuda grass to 56.70 grams of active ingredient per 0.404 hectares, the Valent X-77 ST added 0.25% v / v and the sarcosinates to an equivalent active concentration. 0.75% v-v and double the level. 1.50% The data is shown in Table 1 below. At 7 days after the application, only a yellowing effect was observed and control could not be classified in percent (Table 1). The control was achieved in DAT 14 and the data seem to show that the addition of sodium cocoyl sarcosinate at 1.5% v-v and sarcosinate d? sodium lauroyl at both 0.75% and 1.5% v-v increased the activity of the herbicide FUSILADE «on grass d? Bermuda common. At 31 days after application, the 0.75% v / v of sodium cocoyl sarcosinate and sodium lauroyl sarcosinate gave better control, but all experimental adjuvants gave superior control to that of X-77. TABLE 1 Herbicide: Fusilado 2000 Grass: Bermuda grass Use regime 56.70 gr /, 404 hectare Growth stage: Post Volume d? Spraying: 86.53 liters / .404 hectare Type of Land: Lawn Control Adjuvant: X-77 Usage Regime% Adjuvant Control% V / V 7 DAT 14 DAT 31 DAT 121 DAT 362 DAT X-77 (90% active 0.25 1. 5 4 0 1 -5 0 0 Na cocoyl sarcosinate (30% active) 0.75 2 5 5 0 7 0 0 0 Na cocoyl sarcosinate (30% active) 1.50 3 0 6 5 5 0 0 0 Lauroyl Sarcoxinate Na (30% active) 0.75 3.0 7 5 6 5 0 0 Lauroyl Na Sarcosinate (30% active) 1.50 2, 5 7 0 4 0 0 0 Verification 0 0 0 0 0 EXAMPLE 2 Fuazifop-P-butyl was added to solutions of sodium cocoyl sarcosinate and sodium lauroyl sarcosinate. Valent X-77 was used as control. The Valent X-77 is 90% active and the sarcosinate solutions are 30% active. Four test systems and control were tested for effectiveness in controlling Quack grass. The plots were 3,048 m x 18.29 m planted in a lawn of grass type Quack and the center of 1.83 of each plot was sprayed, leaving 61 cms. of checks on the outside of each plot. Quack-type grass classifications were visual calculations of% control based on a scale of 0-100, where 0 is equal to no control and 100 is equal to full control. Rankings of date seven were carried out, fourteen, thirty, fifty-three and two hundred and ninety of the effects. Fuazifop-P-butyl was applied to Quack grass at 56.70 grams of active ingredient per 0.404 hectares, Valent X-77 was added at 0.25% v / v and sarcosinates at an equivalent active concentration, 0.75 v / v and twice the level. 1.50% The data are shown below in Table 2. The sample containing sarcosinate d? Sodium cocoyl at 0.756. v / v resulted in slower initial activity than the sample used at a higher regimen, but at 14 days after the treatment (DAT) activity of the two regimens was the same and remained the same for the rest of the test. Conversely, the regime under d? Sodium lauroyl sarcosinate resulted in initial activity faster than the superior regimen. The activity for the two regimes was equal to 14 DAT. For 290 DAT, only the sample with the superior lauroyl sodium sarcosinate regime showed any continuous activity on the grass d? Quack. TABLE 2 CONTROL OF QUACK-TYPE PASTE WITH N-ACID FUSILADE AND SARCOSINATE Herbicide: Fusilated 2000 Grass: Quack type Grass Use Regime: 56.70 grams / .404 hectare Growth Stage: Post Spray Volume: 75.70 liters / .404 hectare Type of Land: Adjuvant Control Lawn: X-77 Regime d? Use% d? Adjuvant Control V / V 7 DAT 14 DAT 30 DAT 53 DAT 250 DAT X-77 (90% active) 0 .25 1 0 4 0 3 0 Na cocoyl sarcosinate (30% active 0 .75 3 0 2 5 Na cocoyl sarcosinate (30% active) 1 .50 3 0 3 0 2 5 Sarcosinate d? Lauroyl d? Na (30% Active 0, .75 3 0 1 5 1 5 Na lauroyl sarcosinate (30% active 1. 50 1 0 2 0 1 5 40 EXAMPLE 3 ST added Fuazifop-P-butyl to solutions of sarcosinate d? sodium cocoyl and lauroyl sarcosinate d? sodium. S? he used Valent X-77 as control. The Valent X-77 is 90% active and the sarcosinate solutions are 30% active. Four systems were tested d? test and control for effectiveness when controlling Quack grass. The plots were 3.05 m x 18.29 m sown with Quack grass, which was spring-loaded, disc and cut. The center of 1.83 of each plot was sprayed leaving 61 cms. of test checks on the outside of each plot. Quack-type pasture classifications were visual calculations of% control based on a scale of 0-100. where 0 is equal to no control and 100 is equal to complete control. Classifications were carried out on the date seven, fourteen, thirty-two hundred and seventy-nine of the effects. Fuazifop-P-butyl was applied to Quack grass at 56.70 grams of active ingredient per .404 hectare, Valßnt X-77 was added at 0.25% v / v and sarcosinates at an equivalent active concentration, 0.75% v / v and double the level. 1.50% The data are shown below in Table 3. All the additives showed similar regime response with Fuazifop-P-butyl. ST display substantial control still as of 279 DAT.
TABLE 3 CONTROL OF QUACK TYPE PASTE WITH FUSILADE AND SARCOSINATE OF N-ACIL Herbicide: Splinter 2000 Grass: Quack grass Use regime: 56.70 grams / .404 hectare Growth Stage: Post Spraying Volume: 75.70 liters / .404 hectare Type of Land: Labrada Adjuvant Control: X-77 Regimen of Use% of Adjuvant Control% V / V 7 DAT 14 DAT 30 DAT 279 DAT X-77 (90% Active) 0.25 1 0 6 0 8 5 7 0 Na Cocoyl Sarcosinate (30% active) 0.75 1 0 5 5 9 0 7 0 Sarcosinate de Cocoilo d? Na (30% active) 1.50 1 0 5 5 8 5 8 0 Sarcosinate de Lauroilo d? Na (30% active) 0.75 1 0 5 0 8 0 6 0 Lauroyl Na Sarcosinate (30% active) 1.50 10 5 5 9 0 7 5

Claims (16)

CLAIMS.
1. - A herbicidal composition characterized in that it comprises an effective herbicidally effective amount d? butyl-2- [4- [[5- (trifluoromethyl) -2-pyridinyl] oxy] phenoxy] propanoate and an activator comprising an N-acyl sarcosinate or a salt thereof having the formula:
RCON (CH3) CH2CCOX wherein R is alkyl or alkenyl of Ce to C22. and X is hydrogen, alkali metal, ammonium, Ci-Cβ alkylamine or an amino alcohol. 2. The herbicidal composition of claim 1, characterized in that butyl-2- [4- [[5- (trifluoromethyl) -2-pyridinyl] oxy] phenoxy] propanoate is (R) -2- [4- [[ 5- (Trifluoromethyl) -2-pyridinyl] oxy] phenoxy] propane butyl. 3- The herbicidal composition d? Claim 1, characterized in that the sarcosinate of
N-acyl is selected from the group consisting of alkali metal salts of lauroyl sarcosinate, alkali metal salts of cocoyl sarcosinate, and a mixture of an alkali metal salt of lauroyl sarcosinate and an alkali metal salt of cocoyl sarcosinate.
4. - The herbicidal composition of claim 2, characterized in that the N-acyl sarcosinate is selected from the group consisting of alkali metal salts of lauroyl sarcosinate, alkali metal salts d? cocoyl sarcosinate, and a mixture of an alkaline metal salt of sarcosinate d? lauroyl and an alkali metal salt of cocoyl sarcosinate.
5. The herbicidal composition of claim 1, characterized in that the activator is sodium lauroyl sarcosinate.
6. The herbicidal composition of claim 2. characterized in that the activator TS sarcosinate lauroyl sodium.
7. The herbicidal composition of claim 1. characterized in that the TS coco sarcosinate sodium activator.
8. The herbicidal composition of claim 2, characterized in that the TS coco sarcosinate sodium activator.
9. A method for controlling weeds in grass, characterized in that I understand to apply to the grass an effective amount of a herbicidal composition comprising butyl-2- [4- [[5-]. { trifluoromethyl) -2-pyridinyl] oxy] phenoxy] propanoate and an activator comprising an N-acyl sarcosinate or a salt thereof having the formula: RCON (CH3) CH2COOX wherein R is alkyl or alkenyl d? Ce to C22, and X is hydrogen, alkali metal, ammonium, alkylamine d? Ci-Cß or an amino alcohol. 10.- The method d? claim 9, characterized in that? l -butyl-2- [4- [[5- (trifluoromethyl) -2-pyridinyl] oxy] phenoxy] propanoate is (R) -2- [4- [[5- (trifluoromethyl) - 2-pyridinyl] oxy] phenoxy] -propanoate d? butyl. 11.- The method d? claim 9, characterized in that the TS sarcosinate activator d? sodium lauroyl. 12. The method of claim 10, characterized in that the activator is sodium lauroyl sarcosinate. 13. The method of claim 9, characterized in that the activator is sodium cocoyl sarcosinate. 14.- The method d? Claim 10, characterized in that the activator is sodium cocoyl sarcosinate. 15. The method of claim 9, characterized in that the activator is present in the herbicidal composition in a concentration d? 0.75% or less. 16. The method of claim 10, characterized in that the activator is present in the herbicidal composition in a concentration of 0.75% or less.
MX9800446A 1995-07-19 1996-06-11 Sarcosinates as fluazifop-butyl adjuvants and activators. MX9800446A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/504,273 US5686391A (en) 1995-07-19 1995-07-19 Sarcosinates as fluazifop-butyl adjuvants and activators
US08504273 1995-07-19
PCT/US1996/010049 WO1997003560A1 (en) 1995-07-19 1996-06-11 Sarcosinates as fluazifop-butyl adjuvants and activators

Publications (2)

Publication Number Publication Date
MXPA98000446A true MXPA98000446A (en) 1998-04-01
MX9800446A MX9800446A (en) 1998-04-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
MX9800446A MX9800446A (en) 1995-07-19 1996-06-11 Sarcosinates as fluazifop-butyl adjuvants and activators.

Country Status (10)

Country Link
US (1) US5686391A (en)
JP (1) JPH11509549A (en)
CN (1) CN1126448C (en)
AU (1) AU698125B2 (en)
BR (1) BR9609690A (en)
CA (1) CA2223619C (en)
DE (1) DE29623549U1 (en)
MX (1) MX9800446A (en)
TW (1) TW328902B (en)
WO (1) WO1997003560A1 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6060431A (en) * 1996-09-09 2000-05-09 Ash; David Formulation and process for the selective control of Bermuda and other grasses in Bentgrass, Kentucky Bluegrass, Dichondera, Fine Fescue, Tall Fescue, Annual and perennial Ryegrass and St. Augustinegrass turfs and Iceplant
US5981471A (en) 1997-02-06 1999-11-09 Entremed, Inc. Compositions and methods for inhibiting cellular proliferation
IES970766A2 (en) * 1997-10-24 1999-05-05 Barclay Chemicals R & D Ltd A herbicidal composition comprising glyphosate (N-phosphonomethyl glycine) and an N-acyl sarcosinate
US5985798A (en) * 1998-06-04 1999-11-16 Hampshire Chemical Corp. N-acyl sarcosinates as glyphosate adjuvants
EP1115283B1 (en) 1998-09-23 2003-09-03 Hampshire Chemical Corporation Sarcosinates as glufosinate adjuvants
US6908882B1 (en) * 1999-09-09 2005-06-21 Monsanto Company Enhanced method of killing weeds with glyphosate herbicide
US8326011B2 (en) * 2008-05-21 2012-12-04 Varian Medical Systems, Inc. Methods, systems, and computer-program products for estimating scattered radiation in radiographic projections
US9743663B2 (en) 2010-06-24 2017-08-29 Compo GmbH & Co., KG Pelargonic acid formulation
CN105454246B (en) * 2014-09-24 2017-12-05 南京华洲药业有限公司 A kind of mixed herbicide containing sulfentrazone and the spirit of pyrrole fluorine first standing grain
CN104403674B (en) * 2014-12-15 2017-11-14 成都新朝阳作物科学有限公司 Soil conditioner for adjusting soil physical and chemical property and preparation method thereof
US10957445B2 (en) 2017-10-05 2021-03-23 Hill-Rom Services, Inc. Caregiver and staff information system

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4325729A (en) * 1977-12-13 1982-04-20 Ciba-Geigy Corporation Herbicidal and plant growth regulating pyridyloxy-phenoxy-propionic acid derivatives
US4552580A (en) * 1982-03-11 1985-11-12 Ciba Geigy Corporation Use of N-acyl sarcosinate and its salts as compatibility agents for pesticide/liquid fertilizer formulations

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