CA1129664A - Method of combating weeds in cereal crops and herbicidal formulations therefor - Google Patents

Method of combating weeds in cereal crops and herbicidal formulations therefor

Info

Publication number
CA1129664A
CA1129664A CA331,753A CA331753A CA1129664A CA 1129664 A CA1129664 A CA 1129664A CA 331753 A CA331753 A CA 331753A CA 1129664 A CA1129664 A CA 1129664A
Authority
CA
Canada
Prior art keywords
formula
compound
rate
crop
mecoprop
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.)
Expired
Application number
CA331,753A
Other languages
French (fr)
Inventor
Jean M. Beraud
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.)
Lilly Industries Ltd
Original Assignee
Lilly 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 Lilly Industries Ltd filed Critical Lilly Industries Ltd
Application granted granted Critical
Publication of CA1129664A publication Critical patent/CA1129664A/en
Expired legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N39/00Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02Aryloxy-carboxylic acids; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N39/00Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04Aryloxy-acetic acids; Derivatives thereof

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

ABSTRACT
The selective control of weeds in post-emergence treatment of cereal crops employing a combination of a compound of formula I

(I) and a compound of formula II

(II) wherein X is -CH(CH3)-, the treatment being shown to be synergistic, particularly in controlling the problematic weed species Matricaria spp ABSTRACT
The selcetive control of weeds tn post-emerging trentment of cereal crops employing a combination of an compound of formula I

(I) and a compound of formula 11 (II)

Description

~LZ91664
-2-METHOD OF COMBATING W~EDS IN CEREAL CROPS
AND HERBICIDAL FORMULATIONS THEREFOR

The invention relates to a method of combating weeds in cereal crops and to herbicidal formulations for use in such method.
Heretofore, the broadleaf weed species Matricaria spp has proved particularly resistant to conventional herbicides, causing much damage to winterand spring cereal crops such as wheat, barley, oats and rye. I have now found that by using a combination of particular known herbicides this weed species is controlled to a surprisingly high level, synergism, in accorclance with the well-known "Colby Equation" (Weeds, 15, 2û-22, 1967)9 being observed.
Additionally, control of other problematic weed species has been found to be very satisfactory when using the combination, synergism again being observed in several cases.
Thus, according to the present invention a method of combatin9 weeds in a cereal crop locus comprises applying to said locus, post emergence the crop, a compound of formula 1, f - o CH3U-~ Cl '~ 2~ ~--3 ~ c~ -and a compound of formula 11, ' ~ _ CH3 ¦. Cl { ~ 0-X-C00H (II~

~`` .

, :`~ , ;' .
' ' '.
~ :

_ 3_ J;~LZ966i41 wherein X is -CH(CH3)-, said c~o~d of fo~la II being optionally ~n a salt or ester form ~ich is non-phytotoxic to cereals, the compo~d of fo~Tr~la I being applied at a rate of 0.25 to 3.0 kg/ha and the rx)lTpound of fonrula II be~ng applied at a rate of 0.5 to 3.0 kg/ha; the crop being other than spring ~eat.
In general, the compoond of formula I is applied at Q rate of from 0.7 to 2.û kg/ha qnd the compound of formula 11 at a rate of from 0.7 to 3.û kg!ha.
The compound of formula I is known as bifenox, the preparation thereof being described in United Kingdom Patent Specification No. 1,232,368 and its useas a herbicide being described in Pl~c. N E Weed S~: Conl 1973, 27, 31.
The compound of formula 11, is known as mecoprop.
ta Mecoprop, its salts and esters, its manufacture and its herbicidal properties are well documented in the literature.
The compound of formula 11 may be employed in free acid form or in a salt or ester form which is non-phytotoxic to cereals. As examples of salt forms may be given the alkali-metal,e.g. sodium and potassium, salt forrns and the ammonium, alkylammonium and alkanolammonium salt forms, e.g. the ethanolammonium salt form. As examples of ester forms may be given the lower, e.g. Cl 8' alkyl ester forms, e.g. the methyl and octyl ester forms. The use of such salts and ester forms is embraced by the present invention.
in the method of the present invention, the compound of formula I
bifenox) is preferably employed at an application rate of from û.7 to 1.5 kg/ha and niore preferably at a rate of about 0.75 to l.û kg/ha. The compound of formula 11, mecoprop,is preferably employed at an application rate of from 1.0 to 2.û kg/ha.
The weight ratio of the compound of formula I to the compound(s) of formula 11 is generally in the range of from 1:4 to 3:1, the weight ratio of theformer to the lalter being preferably in the range of from 1:3 to 1.5:1, more preferablyabout 1:2.

~, t ,~

~lZ~6~

In the case of the compound of formuia il, the above weignts and ratios are basec! on tbe acid equivalent t~ereof if a salt or ester is emp10ye~l.
The method of the present invention is preferably carried out when the crop is between the one leaf stage and appearance of the second node, The preferred crops for treatment by the method of the present invention are winter wheat. spring barley and winter barley.
The compound of formula I and the compound of formula 11 may be applied together or separately. If the latter, the time period between applications is preferably short, say one day or less. It is by far preferred, however, for the compounds to be applied simultaneously as a single formulation. In order to simplify manufacture, storage and transport, herbicidal formulations will normally be produced in concentrate form intended for dilotion in water to the degree necessary to enable the above application rates to be achieved. Such concentrate fnrmulations mcy contain from ! to UYQ~ preferably 15 to 85%~ by weight of active ingredients associated with one or more inert, non phytotoxic, carriers therefor. Such formulations will usually be in the form of a wettahle powder, an emulsifiable concentrate or an aqueous suspension or solution.
Herbicidal formulations form a further aspect of the present invention.
Thus, there is provided a helbicidal formulation to be used in the method of theinvention, after dilution if appropriate, and comprising a compound of f~rmula Iand a compound of formula 11, or a salt or ester thereof, in a weight ratio range of from 1:4 to 3:1 (based on the acid equivalent of the compound of formula 11) together with a non-phytotoxic diluent or carrier. The preferred weight ratio ranges are as given above.

. . _ .

,' , . ', ~ 3L2~6~

The herbicidal formulations of the present invention are intended to embrace not only the so-called concentrate formulation forms, but also ready-to-use dilute formulations such as tank mixes and application spray liquors. Such dilute formulations are generally produced by dilution down to the appropriate degree of concentrate formulations but, if desired, may be produced by the separate addition of appropriate amounts of the individual components to an appropriate diluent or carrier.
Turning, however, to the concentrate formulations, wettable powders comprise an intimate mixture of the active ingredients, one or more inert carriers and one or more appropriate surfactants. The inert carrier may be chosen from the attapulgite clays, the montmorillonite clays, the diatomaceous earths, kaolins, micas, talcs and purified silicates. ~ffective surfactants may be found among the sulphonated lignins, the napththalene slllphonates and condensed napthalene sulphonates, the alkyl succ~lates, the alkylbenzene sulphonates, the alkyl sulphates and non-ionic surfactants such as ethylene oxide adducts of phenol. Illustrative wettable powders are those having the following composition:

WETTABLE POWDERS
% by weight Compound of formula 1 1 to 73 Compound of formula 11* 1 to 79 Surfactant(s) 1 to 10 Dispersing Agent 0 to 10 Anticaking Agent 0 to 10 Inert carrier(s) to 100 *based on acid equivalent ,~
. . , : - ,. -: :
: .
: :: :: , - ; :
: : : "
: ., :
. , :. . ,: :: ~ .

~.~;2~64~

Emulsifiable concentrates comprise the active ingredients dissolved in one or more suitab!e solvents, together with a surfactant. As examples of solvents may ~e given alkyl substituted benzenes, o-chlorotoluene, heavy aromatic naphthalenes, glycol ethers and cyclic ketones. Illustrative emulsifiable concentrates are those having the following composition: --~MULSIFIABLE CONCENTRATES
% weight/volume ~--Compound of f ormu la I I to 55 Compound of formula 11* I to 6û
Surfactant(s) 2 to lû ~, Co-solvent û to 4û
Solvent to 100 * eased o~ acid equivulent Aqueous suspensions and solutions comprise the active ingredients suspended or dissolved in water together with any desired surfactants, thickening ngents, antifreezing agents or preservatives. Suitable surfactants may be chosenfrom those mentioned above in connection with wettable powders. Thickening agents? if used, are normally chosen from appropriate cellulose materials and natural gums whilst glycols will generally be used when an antifreezing agent isrequired. Preservatives may be chosen from a wide range of materials such as `
the various paraben antibacterials? phenol, o-chlorocresol, phenyl mercuric nitrate and formaldehyde. Illustrative aqueous suspensions are those having the following composition ~

3Lz~ 6 AQUEOUS SUSPENSIONS
Y~ weight/volume ~ompound of formula 4 tP 59 Compound of formula 11* 5 to 65 Wetting Agent 0 to 10 Dispersing Agent 0 to 6 Thickening/Suspending Agent 0 to 5 Antifreeze Agent 0 to 15 Preservat ive 0 to 2 ~ Water to 1 0û

* Based on acid equivalent The aqueous suspension and wettable powder formulations are preferred for use in the method of the present invention, giving significnntly lower ;phytotoxicity to the cereal crop than the emulsifiable concentrate formulations~
The following Examples further illustrate the invention . In all Examples, the amount of mecoprop used is based on the acid equivalent.

The following wettable powders were prepared, in each case ha\~ing the ingredients shown:
% by weiaht 2 o ( I ) Bif enox 20 Mecoprop (potassium salt) 4û
Sodium Icuryl sulphate 3 Sodium lignin sulphonate 3 Precipitated silica 8 Kaolin to 100 f, ~

' ' ' ': '' : ~
: . :
:' : '~ ':
:, " '' ;':' '' :, 5Li~6~L i % by weight ~2) Bif~n--x ?n Mecoprop (Sodium sal t) 27 Ethoxylated alkyl phenol 4 Lignosulphonate 3 ~
Fumed Silica 6 Attapulgite to lOû
% by weight -
(3) Bifenox 10 Mecoprop (diethanolamine salt) 25 Sodium salt of condensed naphthalene sulphonic acids 6 Precipitated silica 10 Sodium alumin~,silicate to 100 In each E)~ample, the active ingredients were carefully blended with the specified excipients in conventional mixing equipm~ent. qhe blend was then further milled in a fluid energy mill to a size range of from I to 10 microns , ~o The following emulsifiable concentrates were prepared having the constituents shown below:
. .
% by weight/
by volume
(4) Bifenox 15 Mecoprop 30 Calcium dodecylbenzene suiphonate 3 A!kyl phenoxypolyoxyethylene ethanols 3 ~ Isophorone 20 3~ Xylene to 100 ~:

~2~66~

% by weight/
t~y volume
(5) Bifenox 15 Mecoprop ester 20 Alkyl aryl sulphonate 4 Polyoxyethylene triglyceride 4 Cyclohexanone 20 Orthochlorotoluene to 100 % hy weight/
by volume
(6) Bifenox ! 0 Mecoprop 25 Amine salt of dodecylbenzene sulphonic acid 3 Polyoxyethylene sorbital f atty esters 4 Isophorone I S
Heavy aromatic naphtha to 100 The active ingredients were added to the appropriate solvent(s) with stirring and optional heating-to facilitate dissolution of the active materials.B The surfactants were then added. The soiutions were then filtered to remove insoluble impurities, , The following aqueous suspension was prepared having the constituents shown below:

, , , - - ~

' .
, , ' ~ Z~6~
(7) % by weight Bifenox 25 Mecoprop (amine salt) 50 ~ydroxyethyl cellulose 0.5 Phosphate ester 3 Ethylene glycol 2 Water to 100 The following Examples serve to illustrate the synergistic effect demonstrated by the method of the invention.

Several field trials were carried out on winter wheat and one on spring barley on sandy and clay loam soils. Applications were made as tank mixtures with a knapsack sprayer at a volume of 300-800 l/lla. The crop stage at application varied from the start of tillering to the stage at which the second node was visible. Visual assessments of herbicidal activity were made from 2 to 15 weeks a~ter application using the Barratt and Horsfall (1945) rating system.
In the following table is set out the average of the results obtained in terms of percent control of the weed species Matricaria spp for the individual herbicides Bifenox, and mecoprop and for the tank mix combinations of Bifenox + mecoprop, there also being given the control value estimated by the Colby formula for additive effect. The concentrates from which the aqueous spray liquors were formed were Bifenox 80% wettable power and mecoprop 55 aqueous solution and M.C.P.A. 40% aqueous solution.

~-, . . . . .
: ., . .: :

. : -,:

TABLE
~ ontro!
Dosage Rate Kg/ha Observed Colby formula Bifenox l.û 16.1 N/A
Bifenox 1.5 25.~ N/A
Bifenox 2.0 40.3 N/A
Mecoprop (amine salt) 2.0 54.8 N/A

Bifenox ~ mecoprop (amine salt) 1.0+ 2.0 86.0 62.1 " I.S+ 2.û 89.0 66.3 Thus, from the above it can be seen that a genuine synergistic effect is observed when employing the method of the present invention.
Slight scorching of the crop was noted, which was subsequently out-grown.
As well as excellent control of the Matricaria spp, the following weed species were well controlled (greater than 8û%j employing, in separate tests, the above combined tank mixes: Anethum graveolens, Capsella bursa-~storis, Centaurea cyanus, _maria officinal!s, Lamium amplexicaule, Papaver rhoeas, Silene spp, Stellaria media and Galium aparine.

This example further illustrates the synergistic effect demonstrated by the combination oF bifenox ~ mecoprop when used for control of the broadleaf weed Matricaria ~e-Winter wheat was sown in France in October at a depth of 3 cm. qnd at arate of 150 kg/hectare. The crop was allowed to grow without treatment until the following March, at which time the crop was at growth stage 4-5 ~see Plant Pathol., 3 1;~ 54J).

~ ~ .
~:
:. :

3L~ 64 Bifeno~ and mecoprop were then applied separately and combined together as a tank mix and sprayed onto the area in which the crop was growing using a knapsack sprayer at a volume rate per hectare of 300 liters. Assessments, as weed control ratings, were made between 2 and 5 weeks after application.

TABLE

Dosage rate g/hectare Matricaria spp - % control Bifenox 1000 6 Bifenox 1500 15 Bifenox ~ Mecoprop 1000 + 2000 87 Bifenox ~ Mecoprop 1500 ~ 2000 88 Mecoprop 2000 50 ._L~

, .'.. , ~' ' '~- .
~ -. .

Claims (12)

1. A method of combating broadleaf weeds in a cereal crop locus comprising applying to said locus, post emergence the crop, a compound of formula I, (I) and one or more compounds of formula II

(II) wherein X is -CH(CH3)-, said compounds of formula II being optionally in a salt or ester form which is non-phytotoxic to cereals, the compound of formula I being applied at a rate of 0. 25 to 3. 0 kg/ha and the compound of formula II being applied at a rate of 0.5 to 3.0 kg/ha, the crop being other than spring wheat.
2. A method according to claim 1, wherein the compound of formula I is applied at a rate of 0.7 to 2.0 kg/ha and the compound of formula II at a rate of 0.7 to 3.0 kg/ha.
3. A method according to claim I, wherein the compound of formula I is applied at a rate of from 0.7 to 1.5 kg/ha.
4. A method according to claim 1, wherein the compound of formula I is applied at a rate of 0.75 to 1.0 kg/ha.
5. A method according to claim 4, wherein the compound of formula II
is applied at a rate of from 1.0 to 2.0 kg/ha.
6. A method according to claim 1, wherein the weight ratio of the compound of formula I to the compound of formula II is in the range 1:4 to 3:1.
7. A method according to claim 6, wherein the weight ratio of the compound of formula I to the compound of formula II is in the range of 1:3 to 1.5:1.
8. A method according to claim 1, wherein the crop is a winter wheat spring barley, or winter barley crop.
9. A method according to claim 1, wherein the crop is sprayed with spray application liquor formed by addition of water to an aqueous suspension or wettable powder formulation containing the compounds of formulae I and II.
10. A method according to claim 1, wherein the compound of formula II
is in a salt or ester form non-phytotoxic to cereal crops.
11. A herbicidal composition comprising a compound of formula I, stated in claim 1, and a compound of formula II, stated in claim 1, to be used at the rates and in the crops stated in claim 1, the weight ratio of the compound of formula I to the compound of formula II being in the range of 1:4 to 3:1.
12. A composition according to claim 11 in the form of an aqueous suspension or a wettable powder.
CA331,753A 1978-07-15 1979-07-13 Method of combating weeds in cereal crops and herbicidal formulations therefor Expired CA1129664A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB29989/78 1978-07-15
GB7829989A GB2027344A (en) 1978-07-15 1978-07-15 Herbicidal formulation

Publications (1)

Publication Number Publication Date
CA1129664A true CA1129664A (en) 1982-08-17

Family

ID=10498452

Family Applications (1)

Application Number Title Priority Date Filing Date
CA331,753A Expired CA1129664A (en) 1978-07-15 1979-07-13 Method of combating weeds in cereal crops and herbicidal formulations therefor

Country Status (6)

Country Link
JP (1) JPS5515483A (en)
BE (1) BE877675A (en)
CA (1) CA1129664A (en)
CS (1) CS209930B2 (en)
GB (2) GB2027344A (en)
ZA (1) ZA793515B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0231657Y2 (en) * 1986-10-15 1990-08-27

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5635164B2 (en) * 1973-11-28 1981-08-15
JPS50125030A (en) * 1974-03-23 1975-10-01

Also Published As

Publication number Publication date
GB2031279B (en) 1983-02-16
ZA793515B (en) 1981-02-25
JPS5515483A (en) 1980-02-02
GB2031279A (en) 1980-04-23
CS209930B2 (en) 1981-12-31
BE877675A (en) 1980-01-14
GB2027344A (en) 1980-02-20

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