EP0906018A1 - Tensioactifs d'adjuvants agrochimiques - Google Patents

Tensioactifs d'adjuvants agrochimiques

Info

Publication number
EP0906018A1
EP0906018A1 EP97924150A EP97924150A EP0906018A1 EP 0906018 A1 EP0906018 A1 EP 0906018A1 EP 97924150 A EP97924150 A EP 97924150A EP 97924150 A EP97924150 A EP 97924150A EP 0906018 A1 EP0906018 A1 EP 0906018A1
Authority
EP
European Patent Office
Prior art keywords
weeds
formula
group
compound
alkyl
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP97924150A
Other languages
German (de)
English (en)
Inventor
Mahroussa Auda
Steven Irene Jozef Reekmans
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of EP0906018A1 publication Critical patent/EP0906018A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • This invention relates to the use of certain surfactants as adjuvants in agrochemical formulations, particularly herbicidal compositions using gylphosate and similar herbicides
  • R 2 H C CO R 5 1 2 3 4 5 1 2 where R , R R , R and R have defined meanings (generally one of R and R is an alkyl or
  • R is an -NR R group, a different ammo group or a polyoxyaikylene group which may include a substituent at the end of the chain
  • the application describes various uses for these compounds, including as laundry detergents, pigment dispersant surfactants and as adjuvant surfactants in agrochemical formulations including as adjuvants in herbicidal compositions based on glyphosate type herbicides.
  • the application rate to ensure effectiveness against difficult to kill weeds, particularly broad leaved weeds is typically about 30 to 50% higher than would be needed to kill general weeds It would be very desirable to have an adjuvant that would make such herbicides as effective against the difficult to kill weeds as they now are against the relatively easier to kill weeds
  • the present invention is based on our discovery that the surfactants of our earlier PCT case can perform as adjuvants to give enhanced effectiveness of glyphosate type herbicides against weeds, particularly broad leaved and perennial weeds, that are generally relatively more difficult
  • the present invention accordingly provides a method of killing weeds which are difficult to kill, which comprises applying to the weeds a herbicidal composition including as active herbicide a glyphosate type herbicide compound and as adjuvant a compound of the formula (I) (R 1 H) C CO NR 3 R 4 (I)
  • R and R in the succinic acid moiety is C 6 to C 2 2 alkenyl or alkyl and the other is hydrogen
  • R 4 is hydrogen, C 1 to C 22 hydrocarbyl, particularly C 1 to C 20 alkyl
  • R 5 is a group -NR R where R 3 and R 4 are independently as defined above, or R is a group -O (AO) n R where AO is an alkylene oxide, particularly an ethylene oxide, residue, n is 1 to 200, and
  • R is hydrogen, or C 1 to C 22 hydrocarbyl, particularly C 1 to C 6 alkyl
  • the invention is specifically applicable to the use of compounds ot the formula (la) or (lb) (R 1 H) C CO NR 3 R 4 (la) (R 2 H) C CO.NR 3 R 4 or
  • one of R and R in the succinic acid moiety is C 6 to C 12 alkenyl or alkyl and the other is hydrogen, 13 each group R is a glycosyl group, particularly glucosyl group, and each group R is hydrogen, or a C 1 to C 4 alkyl group
  • surfactant adjuvant compounds used in this invention can be made by the methods descnbed in PCT/GB 95/02785 When made by such methods, compounds used in this invention are, as described in that application, typically mixtures of isomers corresponding to the two senses of anhydride ring opening during synthesis
  • the invention particularly includes a method of killing weeds which are difficult to kill, which comprises applying to the weeds a herbicidal composition including as active herbicide a glyphosate type herbicide compound and as adjuvant a compound of the formula (la), particularly formula (la'), and/or (lb) as defined above
  • the invention includes a method of killing weeds which are difficult to kill, which comprises applying to the weeds a herbicidal composition • ncluding as active herbicide a glyphosate amine salt, particularly glyphosate fsopropylamino salt ( ⁇ /-phosphonomethylglyc ⁇ ne /sopropylamine salt), and as adjuvant a compound of the formula (la), particularly formula (la'), and/or (lb) as defined above
  • weeds as being difficult to kill we mean that on application of glyphosate type herbicides, the weeds either require a significantly higher application of herbicide to kill them than the generality of
  • glyphosate type herbicide refers to ⁇ /-phosphonylrr ⁇ ethylglyc ⁇ ne herbicides particularly herbicide compounds of the formula
  • Suitable salt-forming species include alkali metal, particularly sodium, potassium, or rubidium, alkaline earth metal particularly magnesium or calcium, ammonium, primary, secondary, tertiary or quaternary aliphatic ammonium, preferably where the total number of carbon atoms is not more than about twelve, trialkylsulphonium, preferably where the total number of carbon atoms is not more than about six, such as t ⁇ methylsulphonium, ethyl dimethylsulphonium and propyl dimethylsulphonium
  • each M is hydrogen, alkali metal, ammonium, monoalkyi ammonium or trialkylsulphonium moiety.
  • one M is an alkali metal, ammonium, monoalkyi ammonium, or trialkylsulphonium, and two are hydrogen
  • especially preferred compounds include isopropylamine ⁇ /-phosphonomethylglyc ⁇ ne, t ⁇ methylsulphonium ⁇ /-phosphonomethylglyc ⁇ ne and sodium sesqu ⁇ - ⁇ /-phosphonomethyl-glyc ⁇ ne Combinations of two or more such compounds can be used in the present invention
  • the mechanism by which these surfactants are especially effective against difficult to kill weeds is not certain, but is seems that either the surfactant forms lamellar and/or liquid crystalline phases or structures in the coatings on the leaves of the weeds enhancing retention of the active component on the leaf surface, or the adjuvant enhances absorption of the active component into the leaves of the weed (the structures referred
  • the invention is particularly applicable to the use of glyphosate itself ( ⁇ /-phosphonomethy!glyc ⁇ ne /sopropylamine salt) as the surfactants used in the invention are especially effective with glyphosate
  • using glyphosate as the active herbicide with adjuvants used in this invention can give formulations which are more effective, particularly in their effectiveness at lower concentrations and/or in their speed of action, than otherwise similar formulations made using the closely related herbicide sulphosate, which has the same core acid active entity but as the dimethylsulphate salt
  • this use of glyphosate forms a specific aspect of the invention
  • the enhanced herbicidal effect arising from the use of compounds of the formula (I) is particularly noticeable against broad leaved (dicotyledon) weeds especially of the species Chenopodium album, Solanum nigrum, Lactuca saligna, Amaranthus retroflexus and Erigeron canadensis (annuals) and Cirsum arvense (perennial) and similar related weeds from these genera and perennial (generally monocotyledon) weeds of the species Lolium perenne, Convolvulus arvensis and Agropyron repens and similar related weeds from these genera Good and enhanced effects have also been observed against grass (monocotyledon) annual weeds for example of the species Sorghum halepense and similar related weeds indicating the broad spectrum activity of formulations including the adjuvants used in this invention
  • the invention particularly includes a method of killing a weed selected from Chenopodium album, Solanum nigrum, Lactuca saligna Amaranthus retroflexus, Erigeron canadensis and Cirsum arvense and/or a weed selected from Lolium perenne, Convolvulus arvensis and Agropyron repens which comprises applying to the weeds a herbicidal composition including as active herbicide a glyphosate type herbicide compound, particularly ⁇ /-phosphonomethylglyc ⁇ ne /sopropylamine salt, and as adjuvant a compound of the formula (la) or (lb) above, specifically and in particular an adjuvant of the formula (la') above
  • the amounts of the materials used will generally be within the broad ranges typically used in the art with similar materials However, as the compositions used in this invention can be more effective it may be possible to reduce the amount or concentration of the active herbicide as compared with conventional formulations Considered as proportions of spray compositions (so-called 'tank mixes') at current spray volume application rates of about 300 1 ha "1 the concentration of active herbicide will typically be from about 0 05 to about 3%, more usually from about 0 1 to about 0 5 and particularly about 0.2%, and the concentration of adjuvant will typically be from about 0 02 to about 2% more usually from about 0 2 to about 1 % and particularly about 0 1 %
  • the weight ratio of active herbicide to adjuvant surfactant will typically be from about 1 5 to about 10 1 , more usually about 1 2 to about 4'1 and particularly about 2 1 Where low volume spraying methods are used, 5 the concentrations will typically be correspondingly higher, but the ratio of active herbicide to adjuvant will generally remain within the stated ratios
  • the adjuvant surfactants especially those of the formula (1 a'), used in this invention have good compatibility with glyphosate type herbicides, they can be formulated into herbicidal concentrates for dilution to tank mixes In such formulations, the active herbicide will typically be at a concentration of from about 5 to about 60%, more usually from about 10 to about 40% and the ?n adjuvant surfactant, particularly an adjuvant surfactant of the formula (1 a'), at a concentration of from about 3 to about 50%, more usually from about 5 to about 30%, by weight of the concentrate
  • the adjuvants used in this invention can be inco ⁇ orated into aqueous herbicide formulations as such However, we have found that the use of accessories or co-solvents can usefully improve the solubility of the adjuvants as used with the glyphosate herbicides
  • Suitable accessories and 25 co-solvents are generally water soluble and/or miscible organic solvents for the adjuvant surfactants and include glycols, such as ethylene glycol and particularly propylene glycol (so-called 'monopropylene glycol'), low molecular weight polyglycol ethers and their mono alkyl ethers such as di- and t ⁇ -ethylene glycol, di- and tn-propylene glycol and their C, to C 4 mono alkyl ethers and dimethyl isosorbide
  • the proportion of accessory or co-solvent will typically be from 30 about 10 to about 150%, more usually from about 25 to about 75% by weight of the adjuvant used
  • the adjuvant surfactants are much less susceptible to foaming than the alkyl polyglycoside surfactants that have been suggested for use, particularly with sulfosate (N-phosphonomethyl glycine trimethylsulphonium salt).
  • glucamide groups are -N(methyl)(glucosyl) groups and PEG groups are polyethylene glycolyl groups of the stated approximate molecular weight.
  • Example 1 Aqueous herbicide formulations were made up using GAS and GSS as the active agents and using various adjuvants. The formulations were made up as aqueous solutions containing: for glyphosate formulations: for sulphosate formulations: material amount material amount GAS 7.3 mi/ 1 GSS 6.7 ml.l '1 adjuvant 1 .8 ml.l "1 adjuvant 2.0 ml.l '1 composition composition water remainder water remainder
  • the formulations were used in a test spraying programme in which the formulation was sprayed at an application rate of 300 l.ha “1 (thus providing 2.2 l.ha '1 GAS, equivalent to 1276 g.ha '1 active salt and 2.0 l.ha " GSS, equivalent to 1137 g.ha " active salt) onto field test plots containing growing plants of the weeds Erigeron canadensis (ERICA) and Lactuca saligna (LACSA) using 4 replications. The percentage of weed plants killed by the herbicide was assessed after 7, 14 and 28 days and was reported as the % efficacy. The formulations used and the weed control results obtained are summarised in Table 1 below.
  • Example 2 Aqueous herbicide formulations were made up using GAS and GSS as the active agents and using various adjuvants at the concentrations used in Example 1. The formulations were used in a test spraying programme in which the formulation was sprayed, at the rate described in Example 1 , onto greenhouse test plots containing growing plants of the weeds Chenopodium album (CHEAL), Sorghum halepense (SORHA) and Amaranthus retroflexus (AMARE) using 4 replications. The percentage of weed plants killed by the herbicide was assessed after 7, 14 and 28 days and was reported as the % efficacy. The formulations used and the weed control results obtained are summarised in Table 2 below.
  • CHEAL Chenopodium album
  • SORHA Sorghum halepense
  • AMARE Amaranthus retroflexus
  • Example 3 Example 2 was repeated using different adjuvants (and controls) and the formulations and results are summarised in Table 3 below.
  • Example 1 was repeated using adjuvant AF5 (and controls) and the formulations and results are summarised in Table 4 below.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés adjuvants tensioactifs de la formule (I) dans laquelle R?1, R2, R3, R4 et R5¿ ont des désignations prédéterminées et peuvent être utilisés, avec une efficacité particulière, avec des herbicides de type glyphosates en vue d'éliminer des espèces de plantes nuisibles, reconnues comme étant particulièrement difficiles à détruire. Ces plantes nuisibles sont des plantes à larges feuilles (dicotylédon) telles que Chenopodium album, Solanum nigrum, Lactuca saligna, Amaranthus retroflexus et Erigeron canadensis (plantes annuelles) et Cirsum arvense (plante pérenne) et des plantes nuisibles similaires provenant de ces espèces, ainsi que le monocotylédon pérenne tel que Lolium perenne, Convolvulus arvensis et notamment Agropyron repens et des plantes nuisibles similaires provenant de ces espèces.
EP97924150A 1996-06-11 1997-06-02 Tensioactifs d'adjuvants agrochimiques Withdrawn EP0906018A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9612197 1996-06-11
GBGB9612197.5A GB9612197D0 (en) 1996-06-11 1996-06-11 Agrochemical adjuvant surfactants
PCT/GB1997/001484 WO1997047199A1 (fr) 1996-06-11 1997-06-02 Tensioactifs d'adjuvants agrochimiques

Publications (1)

Publication Number Publication Date
EP0906018A1 true EP0906018A1 (fr) 1999-04-07

Family

ID=10795115

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97924150A Withdrawn EP0906018A1 (fr) 1996-06-11 1997-06-02 Tensioactifs d'adjuvants agrochimiques

Country Status (11)

Country Link
EP (1) EP0906018A1 (fr)
JP (1) JP2000511924A (fr)
KR (1) KR20000016480A (fr)
AR (1) AR007556A1 (fr)
AU (1) AU2971797A (fr)
BR (1) BR9709777A (fr)
CA (1) CA2255600A1 (fr)
GB (1) GB9612197D0 (fr)
NZ (1) NZ332929A (fr)
WO (1) WO1997047199A1 (fr)
ZA (1) ZA975041B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5962400A (en) * 1998-12-22 1999-10-05 National Starch And Chemical Investment Holding Corporation Amino acid copolymers having pendent polysaccharide moieties and uses thereof
US6218336B1 (en) 1999-10-26 2001-04-17 Applied Carbochemicals Enhanced herbicides
MY158895A (en) 2000-05-19 2016-11-30 Monsanto Technology Llc Potassium glyphosate formulations
KR101929393B1 (ko) 2017-11-15 2018-12-17 대한민국 이탈리안라이그라스로부터 퀴닌을 추출 및 정제하는 방법

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9424353D0 (en) * 1994-12-02 1995-01-18 Ici Plc Surfactants

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9747199A1 *

Also Published As

Publication number Publication date
BR9709777A (pt) 1999-08-10
WO1997047199A1 (fr) 1997-12-18
NZ332929A (en) 2000-08-25
AU2971797A (en) 1998-01-07
GB9612197D0 (en) 1996-08-14
ZA975041B (en) 1997-12-11
KR20000016480A (ko) 2000-03-25
AR007556A1 (es) 1999-11-10
CA2255600A1 (fr) 1997-12-18
JP2000511924A (ja) 2000-09-12

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