CA1287570C - Aqueous suspension concentrate compositions of pendimethalin - Google Patents
Aqueous suspension concentrate compositions of pendimethalinInfo
- Publication number
- CA1287570C CA1287570C CA000537637A CA537637A CA1287570C CA 1287570 C CA1287570 C CA 1287570C CA 000537637 A CA000537637 A CA 000537637A CA 537637 A CA537637 A CA 537637A CA 1287570 C CA1287570 C CA 1287570C
- Authority
- CA
- Canada
- Prior art keywords
- pendimethalin
- weight
- crystal form
- formaldehyde
- composition according
- 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 - Fee Related
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- 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
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Abstract
AQUEOUS SUSPENSION CONCENTRATE COMPOSITIONS OF
PENDIMETHALIN
ABSTRACT OF THE DISCLOSURE
The present invention relates to novel stable aqueous suspension concentrate compositions of the low-melting pesticide pendimethalin, alone or in combination with secondary pesticides which are water soluble or have melting points greater than 70°C. The invention also relates to methods for the preparation of these compositions.
Uniquely, pendimethalin may be present in the compositions of the invention in a ratio of orange crystal form to yellow crystal form of 4:96 up to totally orange crystal form.
PENDIMETHALIN
ABSTRACT OF THE DISCLOSURE
The present invention relates to novel stable aqueous suspension concentrate compositions of the low-melting pesticide pendimethalin, alone or in combination with secondary pesticides which are water soluble or have melting points greater than 70°C. The invention also relates to methods for the preparation of these compositions.
Uniquely, pendimethalin may be present in the compositions of the invention in a ratio of orange crystal form to yellow crystal form of 4:96 up to totally orange crystal form.
Description
~3ju ~Z~7570 A~UE~IlS Sl)SPENSION CONCENTRATE COMPosITIoNs OF
NDI~ETHALIN
BAC~GROUND OF THE INVENTION
Su~p~nsion concentrate or aqueou~ fLowable pesticida1 cornposition~ are conc~ntrated suspen~ions oE water insoluble pe~ticides and mixture~ of pe3ticlde~ in aqueou~ sy6tems. 'r11e pLesent invention S relatee to stable ~uch pendlme~llalln composition~.
Pendimethalln 19 a dlnitroanilLne that exists in poLymorphlc form, both in orange cry~tal form and yellow crystal orm. U.S. Pat~nts 4,0~2,537 and 4,150,969 addrese pendlmethalln'a unlque formu}at~on problem~ a~d provLde ways to avoid formation and/or presence of the larg~r, orange crystal form.
It is believed that the presence oE pendlmethalin in the orahge macrocrystal Eorm re~ult~ in large elongated cry~tals ln final formulation~.
In order to formulate stable wettable powder compositions oE pendimethalin, these two patents disclose utilizlng a ~tabilized pendimethalin, stabillzed ~y the addition oE either sodium dialkyl ~C6-L8~ ~ulfosuccinate or an ethoxylated 8~ diamine.
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NDI~ETHALIN
BAC~GROUND OF THE INVENTION
Su~p~nsion concentrate or aqueou~ fLowable pesticida1 cornposition~ are conc~ntrated suspen~ions oE water insoluble pe~ticides and mixture~ of pe3ticlde~ in aqueou~ sy6tems. 'r11e pLesent invention S relatee to stable ~uch pendlme~llalln composition~.
Pendimethalln 19 a dlnitroanilLne that exists in poLymorphlc form, both in orange cry~tal form and yellow crystal orm. U.S. Pat~nts 4,0~2,537 and 4,150,969 addrese pendlmethalln'a unlque formu}at~on problem~ a~d provLde ways to avoid formation and/or presence of the larg~r, orange crystal form.
It is believed that the presence oE pendlmethalin in the orahge macrocrystal Eorm re~ult~ in large elongated cry~tals ln final formulation~.
In order to formulate stable wettable powder compositions oE pendimethalin, these two patents disclose utilizlng a ~tabilized pendimethalin, stabillzed ~y the addition oE either sodium dialkyl ~C6-L8~ ~ulfosuccinate or an ethoxylated 8~ diamine.
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2 6110~-7532 This technique malntains pendimethalin in the ~ello~ crystal form which does not favor the formation of large elongated crystals in formulated product for the preparation of wettable powders. However, these patents fail to disclose ways to formulate pendimethalin as a stable suspension concentrate cotnposition or aqueous flowable composition with orange crystal forms, which form is favored.
These aqueous compositions frequently conkain about 10%
to 80~, by weight of a solid pesticide or mixture of solid pesticides, thereby providing a method for handling those pesticides which are relatively water lnsoluble in an aqueous medium. Since these ~ypes of compositions have the desirable characteristics of a thick llquid, they may be poured or pumped.
Thus, some of the problems, like dusting that is possible in solid compositions of wettable powders and granulars, are avoided.
Further, these aqueous-based concentrates also have the added advantage of not requiring the use of orga~ic solvents, often present in emulsifiable concentrates.
For these reasons, it is desirable to formulate pesticides into suspension concentrates or aqueous flowables.
~owever, such formulations have their own problems such as gelling, caking and settling, as well as problems because of the physical and chemical characteristics of the pesticide or mixture of pes~icides. Pendimethalln is one of theæe pesticides that ls somewhat dlfflcult to formulate.
Oftentlmes, when pendimethalln in the orange macrocrystal form is found ln compositlons, very large, elongated . ~
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These aqueous compositions frequently conkain about 10%
to 80~, by weight of a solid pesticide or mixture of solid pesticides, thereby providing a method for handling those pesticides which are relatively water lnsoluble in an aqueous medium. Since these ~ypes of compositions have the desirable characteristics of a thick llquid, they may be poured or pumped.
Thus, some of the problems, like dusting that is possible in solid compositions of wettable powders and granulars, are avoided.
Further, these aqueous-based concentrates also have the added advantage of not requiring the use of orga~ic solvents, often present in emulsifiable concentrates.
For these reasons, it is desirable to formulate pesticides into suspension concentrates or aqueous flowables.
~owever, such formulations have their own problems such as gelling, caking and settling, as well as problems because of the physical and chemical characteristics of the pesticide or mixture of pes~icides. Pendimethalln is one of theæe pesticides that ls somewhat dlfflcult to formulate.
Oftentlmes, when pendimethalln in the orange macrocrystal form is found ln compositlons, very large, elongated . ~
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3 ~llOg-75~2 crystals (about 3000 microns in length) appear in final product, resulting in instability, difficulty in processing and unreliability of usage. Thus, formulating compositions wherein these elon~ated crystals do not develop is crucial ~o stability and necessary to obtain even distribution of active compound for application.
The problems associated with the development o~
suspension concentrate compositions containing low melting active in~redients, alone or in combination with higher melting active ingredients, are described in German Patent Application DE 3302648 Al. German Patent Application DE 3302648 Al tries to deal with the problems o~ an aqueous mixed dispersion o~ a low melting active ingredient in a solvent of phthalie acid Cl-C12 alkyl esters in combination with an aqueous suspension concentrate containing one or more active ingredients as an alternative to a suspension concentrate containing low melting active ingredients, such as pendimethalinlN-~l-ethyl-propyl)-2,6-dinitro-3,4-xylidine]. The reason ~or the alternative approach of that application is the inability to prepare stable suspension concentrates by various techniques, including those of European Patent Application 0 33291.2. That EP0 application describes insecticidal suspension concentrate composi~ions of phosalone and adiuvants which may be prepared with molten insecticide. These references do not address ways helpful ~o the development of pendimethalin composltions which utillze the orange crystal form to produce a s~able and evenly efficacious product.
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137~70 3a 6110g-7532 It is an object o~ ~,he present lnvention to provide stable aqueous concentrate compositions of the low meltiny pesticide, pendimethalin, in the orange ~ry.s~al form either alone or in combination wlth secondary pesticide(s) in order to avoid the problem of formation of large elongated crystals of formulated pendimethalin. These secondary pesticides are often ..
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~. : : - ' 4 611~g-753 water insoluble or have meltiny points greater than 70C
It is a further ob~ec~ o~ thls invention ~o provide such s~able aqueous suspension concentrate compositions of pendimethalin having a ratio of orange crystal to yellow crystal of 4,96 to totally ~100~) orange crystal form.
Furthermore, an additional object of the present invention is to provide methods for preparing ~uch stable aqueous suspension concentrate compositions.
These and other objects will become more apparent by the detailed descxiption of the invention provided herein.
The present invention relates to stable aqueous suspension concentrate compositlons or aqueous ~lowable compositions comprising pendimethalin, alone or in combination with secondary pesticides. Compositions of the invention comprise, on a weight to volume basis about 5.0% to 50.0~
pendimethalin having an orange arystal to yellow crystal ratio of about 4t96 up to totally lQ0% orange crystal form; about 0% to 50.0% of one or more secondary pesticides having a melting point of greater than 70C or being water soluble; about 3.0% to 30.0%
of coformulants, such as sur~actants, dispersing agents, wettlng agents, antifreezing agents, antifoaming agents, thickening agents, suspending agents, preservatives and the like which do not solubilize or dissolve the pendlmethalin; and about 20.0~ to 92.0 water.
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4~ 6110~-7532 This invention Purther comprises an aqueous suspension concentrate composition comprlsiny, on a weight to volume basis:
about 5.0% to SO.O~ solid pendlmethalin having A% orange crystal form to 96% yellow crystal form to 100% orange crystal form; about 3.0% to 30.0% non-pestlcidal coformulants; and about 20.0% to 92.0% water.
DETAILED DESCRIPTION OF THE INVENTION
Preferred stable aqueous suspension concentrate compositions of pendimethalin comprise on a weight to volume basis, about 5.0~ to 50.0% pendimethalin, wherein 4.0% of the pendimethalin crystals are the orange crystal form, most preferred 10.0% or more of the pendimethalin crystals are the orange crystal form. Further, the compositions of the present invention also comprise, on a weight to volume basis, about 0% to 50.0% of one or more secondary pesticides being water soluble or having a melting point greater than 70C; about 0.5% to 1.0% an~ifoaming agents;
about 2.0% to 20.0% antifreezing agent; about 2.0% to 20.0%
surfactants dispersing agents, wetting agents, or mixtures thereof; about 0.05% to 3.0% thickening agents; about 0.01% to 1.0% preservatives; and the remainder water to total the composition to 100%.
The present invention further relates to a composition comprising, on a weight to volume basisJ about 5.0% to 50.0% solid pendim~thalin with 10%, on a weight to weight basis, of the orange crystal form; ahout 2.0~ to 20.0% cresol-formaldehyde condensates or sulfonates thereof, naphthalene-formaldehyde condensates or sulfonates thereof; lignosul~onates, or mixtures thereof; about ``~
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The problems associated with the development o~
suspension concentrate compositions containing low melting active in~redients, alone or in combination with higher melting active ingredients, are described in German Patent Application DE 3302648 Al. German Patent Application DE 3302648 Al tries to deal with the problems o~ an aqueous mixed dispersion o~ a low melting active ingredient in a solvent of phthalie acid Cl-C12 alkyl esters in combination with an aqueous suspension concentrate containing one or more active ingredients as an alternative to a suspension concentrate containing low melting active ingredients, such as pendimethalinlN-~l-ethyl-propyl)-2,6-dinitro-3,4-xylidine]. The reason ~or the alternative approach of that application is the inability to prepare stable suspension concentrates by various techniques, including those of European Patent Application 0 33291.2. That EP0 application describes insecticidal suspension concentrate composi~ions of phosalone and adiuvants which may be prepared with molten insecticide. These references do not address ways helpful ~o the development of pendimethalin composltions which utillze the orange crystal form to produce a s~able and evenly efficacious product.
;. .: . , .................... , :
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.
137~70 3a 6110g-7532 It is an object o~ ~,he present lnvention to provide stable aqueous concentrate compositions of the low meltiny pesticide, pendimethalin, in the orange ~ry.s~al form either alone or in combination wlth secondary pesticide(s) in order to avoid the problem of formation of large elongated crystals of formulated pendimethalin. These secondary pesticides are often ..
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~. : : - ' 4 611~g-753 water insoluble or have meltiny points greater than 70C
It is a further ob~ec~ o~ thls invention ~o provide such s~able aqueous suspension concentrate compositions of pendimethalin having a ratio of orange crystal to yellow crystal of 4,96 to totally ~100~) orange crystal form.
Furthermore, an additional object of the present invention is to provide methods for preparing ~uch stable aqueous suspension concentrate compositions.
These and other objects will become more apparent by the detailed descxiption of the invention provided herein.
The present invention relates to stable aqueous suspension concentrate compositlons or aqueous ~lowable compositions comprising pendimethalin, alone or in combination with secondary pesticides. Compositions of the invention comprise, on a weight to volume basis about 5.0% to 50.0~
pendimethalin having an orange arystal to yellow crystal ratio of about 4t96 up to totally lQ0% orange crystal form; about 0% to 50.0% of one or more secondary pesticides having a melting point of greater than 70C or being water soluble; about 3.0% to 30.0%
of coformulants, such as sur~actants, dispersing agents, wettlng agents, antifreezing agents, antifoaming agents, thickening agents, suspending agents, preservatives and the like which do not solubilize or dissolve the pendlmethalin; and about 20.0~ to 92.0 water.
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.. , ' ' , ~ , ' '.'. ' . '' ' . ' ' ` ' ~ ' ~ ' ' ' ' ' ' , ' ' ' . ,' `' . " ~,, " . ' ' ' ' ' ' . ' ' ` . ' , ' . . .. . , ~ . . . . .
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4~ 6110~-7532 This invention Purther comprises an aqueous suspension concentrate composition comprlsiny, on a weight to volume basis:
about 5.0% to SO.O~ solid pendlmethalin having A% orange crystal form to 96% yellow crystal form to 100% orange crystal form; about 3.0% to 30.0% non-pestlcidal coformulants; and about 20.0% to 92.0% water.
DETAILED DESCRIPTION OF THE INVENTION
Preferred stable aqueous suspension concentrate compositions of pendimethalin comprise on a weight to volume basis, about 5.0~ to 50.0% pendimethalin, wherein 4.0% of the pendimethalin crystals are the orange crystal form, most preferred 10.0% or more of the pendimethalin crystals are the orange crystal form. Further, the compositions of the present invention also comprise, on a weight to volume basis, about 0% to 50.0% of one or more secondary pesticides being water soluble or having a melting point greater than 70C; about 0.5% to 1.0% an~ifoaming agents;
about 2.0% to 20.0% antifreezing agent; about 2.0% to 20.0%
surfactants dispersing agents, wetting agents, or mixtures thereof; about 0.05% to 3.0% thickening agents; about 0.01% to 1.0% preservatives; and the remainder water to total the composition to 100%.
The present invention further relates to a composition comprising, on a weight to volume basisJ about 5.0% to 50.0% solid pendim~thalin with 10%, on a weight to weight basis, of the orange crystal form; ahout 2.0~ to 20.0% cresol-formaldehyde condensates or sulfonates thereof, naphthalene-formaldehyde condensates or sulfonates thereof; lignosul~onates, or mixtures thereof; about ``~
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5 6110g-7532 0.05% to 2.5% Xanthan gum, guar gum, gum arahlc, ox cellulose derivatives; about 2.0% to 15.0% ethylene glycol, propylene glycol or urea; about 0.05% to 1.0% anti~oaming agent; about 0.05% to 2.0% thickening agent; about 0.05% to 2.5% preservative; and the remainder water to total said composltion to 100%.
Among preferred embodiments are the follo~ing:
(a) a composltion comprising on a weight to volume basis: about 20.0% to gO.0% pendimethalin; about 3.0% to 5.0%
sodium cresol-formaldehyde condensate or sodium cresol-formaldehyde sulphonated condensate; about 5% to 10% ethylene glycol or urea; about 0.1% to 1.0% siliconic anti~oaming agent;
about 0.1% to 0.3% Xanthan gum; about 0.2% to 1.0% of a 38%
formaldehyde solution; and the balance water.
(b) a composition comprising on a weight to volume basis: 40.0% pendimethalin; 5.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% ethylene glycol; 0.5% siliconic antifoaming agent; 0.2% Xanthan gum; 0.5% o~ a 38% formaldehyde solution; and the balance water.
~c) a compositlon comprising on a weight to volume basis: 27.3% pendimethalin; 18.2% atrazine; 3.4% sodium cresol-formaldehyde sulphonated condensate; 5.8% urea; 1.34% polyalkylene glycol ether and polyoxyethylene alkylaryl ether; 0.9% siliconic antifoaming agent; 0.2% Xanthan gum; 0.5% of a 38% formaldehyde solution; and the balance water.
(d) a composition comprising on a weight to volume basis: 23.6% pendimethalin; 23.6% isoproturon; 3.0% sodium cresol-formaldehyde sulphonated conde~sate; 8.0% urea or ethylene glycol;
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5a 611c)g-7532 2.0% ~thylene oxide-propylene oxide copolymer; 2.0% silica; 0.5 siliconic antifoaming agent; 0.1% 2anthan gum; 0.25% of a 38%
formaldehyde solution; and the balan~e water.
(e) a composition comprising on a weight to volume basis: 30.0% pendimethalln, 5.0% of the water-soluble ammonium salt of 2-~4-iso~ropyl-4-methyl-5-oxo-2-imldazolin-2-yl)-3-quinolinecarboxylic acid; 4.0% sodium lignosulphonate; 8.0%
ethylene glycol, 0.5% siliconic antifoaming agent; 0.75% silica;
0.1% Xanthan gum; 0.25% of a 38% formaldehyde solution; and the balance water.
(f) a composition comprising on a weight to volume basis: 20.0% pendimethalin; 30.0% chlortoluron; 3.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% urea or ethylene glycol; 2.0% ethylene oxide-propylene oxide copolymer; 0.5%
siliconic antifoaming agent; 2.0% silica; 0.05% Xanthan gum; 0.25%
of a 38~ formaldehyde solution; and the balance water.
(g) a composition comprising on a weight to volume basis: 26.0% pendimethalin; 12.5% of an iæomeric mixture of methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-m-toluate and methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-~-toluate;
3.0% sodium cresol-formaldehyde condensate; 1.3% triethanolamine salt of polyarylarylethoxylate phosphate; 6.0% alkylphenol-ethoxylate; 5.0% ethylene glycol; 0.4% siliconic anti~oaming agent; 2.0% siliaa; 0.1% Xanthan gum; 0.25% o~ a 38% ~ormaldehyde solution; and the balance water.
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5b 61109-7532 Cofor~ulants Pesticldes suitable for use in the compositions of the present lnvention include ureas, triazines, imidazolinones, alone or in combination, amongsk just a few. Fungicides, insecticides and plant growth regulators which have melting points greater than 70C and~or possess physical properties which are amenable to the preparation of aqueous suspension concentrate compoeitions also may be used in the compositions of the present invention.
Additionally, water soluble pestlcides, such as difenzoquat, amine salks, alkali or alkali metal salts of ioxynil, bromoxynil, phenoxy acetic acids, and imidazolinyl carboxylic acids such as 2-(4-isopropyl-4-methyl-5-oxo-2-imldazolin-2-yl)-3-quinolinecarboxylic acid and the like may readily be incorporaked into the stable aqueous suspension concentrate compositions of this inven~ion.
Preferred such higher melting component~ for use in the aqueous suspension compositions of the invention containing pendimethalin include, .`$:
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~Z~7~7~) 6 ~llOg-7532 Isoproturon, lN,N-dimethyl-N'-(4-(1-methylethyl)-phenyl)-urea~; ~inuron, [N-(3,4-dichlorophenyl)-N'-me~hoxy-N'-methyl urea]; Mekoxuron, IN'-(3-chloro-4-methoxyphenyl~-~,N-dimethylurea];Chlortoluron, [N'-(3-chloro-4-methyl-phenyl)-N, N-dimethylurea]; Atrazine, ~2-chloro-4-ethyl-amino-6-isopropylamino-1,3,5-triazine; other secondary active components include terbutylazine, 2-tert-butyl-amino-4-chloro-6-ethylamino-1,3,5-triazine and metolachlor, 2-chloro-6'-ethyl-N-(2-methoxy-1-methylethyl)-acet-o-toluidide; Imidazolinone herbicides such as 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-qunolinecarboxylic acid and water soluble salts thereof, and the isomeric mixture of methyl 6-~4-isopropyl-~-methyl-5-oxo-2-imidazolin-2-yl)-m-toluate and methyl 2-(~-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)toluate.
Surfactants (including dispersing agents and/or wetting agents) suitable in the aqueous suspension compositions of the invention containing solid pendimethalin include: ethylene oxide/propylene oxide condensates; alkyl, aryl- and aryl, arylethoxylates and derivatives thereo~; lignosulfonates; cresol-and naphthalene-formaldehyde condensates and sulfonates;
polycarboxylates and derivatives thereof; and mixtures khereof.
In general, anionic polymerics, such as cresol .formaldehyde condensates and their sulfonates, naphthalene formaldehyde condensates and their sulfonates and lignosulfonates have been ~ound to minlmize crystal formation during storage and as such;are most preferred.
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Among preferred embodiments are the follo~ing:
(a) a composltion comprising on a weight to volume basis: about 20.0% to gO.0% pendimethalin; about 3.0% to 5.0%
sodium cresol-formaldehyde condensate or sodium cresol-formaldehyde sulphonated condensate; about 5% to 10% ethylene glycol or urea; about 0.1% to 1.0% siliconic anti~oaming agent;
about 0.1% to 0.3% Xanthan gum; about 0.2% to 1.0% of a 38%
formaldehyde solution; and the balance water.
(b) a composition comprising on a weight to volume basis: 40.0% pendimethalin; 5.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% ethylene glycol; 0.5% siliconic antifoaming agent; 0.2% Xanthan gum; 0.5% o~ a 38% formaldehyde solution; and the balance water.
~c) a compositlon comprising on a weight to volume basis: 27.3% pendimethalin; 18.2% atrazine; 3.4% sodium cresol-formaldehyde sulphonated condensate; 5.8% urea; 1.34% polyalkylene glycol ether and polyoxyethylene alkylaryl ether; 0.9% siliconic antifoaming agent; 0.2% Xanthan gum; 0.5% of a 38% formaldehyde solution; and the balance water.
(d) a composition comprising on a weight to volume basis: 23.6% pendimethalin; 23.6% isoproturon; 3.0% sodium cresol-formaldehyde sulphonated conde~sate; 8.0% urea or ethylene glycol;
.
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5a 611c)g-7532 2.0% ~thylene oxide-propylene oxide copolymer; 2.0% silica; 0.5 siliconic antifoaming agent; 0.1% 2anthan gum; 0.25% of a 38%
formaldehyde solution; and the balan~e water.
(e) a composition comprising on a weight to volume basis: 30.0% pendimethalln, 5.0% of the water-soluble ammonium salt of 2-~4-iso~ropyl-4-methyl-5-oxo-2-imldazolin-2-yl)-3-quinolinecarboxylic acid; 4.0% sodium lignosulphonate; 8.0%
ethylene glycol, 0.5% siliconic antifoaming agent; 0.75% silica;
0.1% Xanthan gum; 0.25% of a 38% formaldehyde solution; and the balance water.
(f) a composition comprising on a weight to volume basis: 20.0% pendimethalin; 30.0% chlortoluron; 3.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% urea or ethylene glycol; 2.0% ethylene oxide-propylene oxide copolymer; 0.5%
siliconic antifoaming agent; 2.0% silica; 0.05% Xanthan gum; 0.25%
of a 38~ formaldehyde solution; and the balance water.
(g) a composition comprising on a weight to volume basis: 26.0% pendimethalin; 12.5% of an iæomeric mixture of methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-m-toluate and methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-~-toluate;
3.0% sodium cresol-formaldehyde condensate; 1.3% triethanolamine salt of polyarylarylethoxylate phosphate; 6.0% alkylphenol-ethoxylate; 5.0% ethylene glycol; 0.4% siliconic anti~oaming agent; 2.0% siliaa; 0.1% Xanthan gum; 0.25% o~ a 38% ~ormaldehyde solution; and the balance water.
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5b 61109-7532 Cofor~ulants Pesticldes suitable for use in the compositions of the present lnvention include ureas, triazines, imidazolinones, alone or in combination, amongsk just a few. Fungicides, insecticides and plant growth regulators which have melting points greater than 70C and~or possess physical properties which are amenable to the preparation of aqueous suspension concentrate compoeitions also may be used in the compositions of the present invention.
Additionally, water soluble pestlcides, such as difenzoquat, amine salks, alkali or alkali metal salts of ioxynil, bromoxynil, phenoxy acetic acids, and imidazolinyl carboxylic acids such as 2-(4-isopropyl-4-methyl-5-oxo-2-imldazolin-2-yl)-3-quinolinecarboxylic acid and the like may readily be incorporaked into the stable aqueous suspension concentrate compositions of this inven~ion.
Preferred such higher melting component~ for use in the aqueous suspension compositions of the invention containing pendimethalin include, .`$:
. . .
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~Z~7~7~) 6 ~llOg-7532 Isoproturon, lN,N-dimethyl-N'-(4-(1-methylethyl)-phenyl)-urea~; ~inuron, [N-(3,4-dichlorophenyl)-N'-me~hoxy-N'-methyl urea]; Mekoxuron, IN'-(3-chloro-4-methoxyphenyl~-~,N-dimethylurea];Chlortoluron, [N'-(3-chloro-4-methyl-phenyl)-N, N-dimethylurea]; Atrazine, ~2-chloro-4-ethyl-amino-6-isopropylamino-1,3,5-triazine; other secondary active components include terbutylazine, 2-tert-butyl-amino-4-chloro-6-ethylamino-1,3,5-triazine and metolachlor, 2-chloro-6'-ethyl-N-(2-methoxy-1-methylethyl)-acet-o-toluidide; Imidazolinone herbicides such as 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-qunolinecarboxylic acid and water soluble salts thereof, and the isomeric mixture of methyl 6-~4-isopropyl-~-methyl-5-oxo-2-imidazolin-2-yl)-m-toluate and methyl 2-(~-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)toluate.
Surfactants (including dispersing agents and/or wetting agents) suitable in the aqueous suspension compositions of the invention containing solid pendimethalin include: ethylene oxide/propylene oxide condensates; alkyl, aryl- and aryl, arylethoxylates and derivatives thereo~; lignosulfonates; cresol-and naphthalene-formaldehyde condensates and sulfonates;
polycarboxylates and derivatives thereof; and mixtures khereof.
In general, anionic polymerics, such as cresol .formaldehyde condensates and their sulfonates, naphthalene formaldehyde condensates and their sulfonates and lignosulfonates have been ~ound to minlmize crystal formation during storage and as such;are most preferred.
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7 6110g-753 Suspending agents su~h as polysaccharlde gums lik~
Xanthan gum, guar gum; yum arabic and cellulose derivatives and the like are suitable for additlon in amounts of about 0~02~ to 3 %r on a weight to volume basis.
Preservatives to prevent microbial spoiling in the compositions of the invention are inclu~ed as necessary. One example is a 38% formaldehyde solution. Other preservatives include methyl or propyl parahydroxyhenzoate, 2-bromo-2-nitro-propane-1,3-diol, sodium benzoate, glutaraldehyde, o-phenylphenol, benziæothiazolinones, 5-chloro-2-methyl-4-i~othiazolin-3-one, pentachlorophenol, 2-4-dichlorobenzyalcohol~ or mixtures thereof and o~hers known to those in the art. Siliconic antifoaming agents are useful in the present compositions.
Ankifreezing agents such as ethylene glycol, propylene glycol, other glycols, glycerine or urea may be added to the aqueous suspension concentrate compositions. Additional surfactants, preservatives and thickening agents, such as clays, precipitated silicas, polyvinyl alcohol, polyvinyl-pyrrolidone, polyacrylamides and the like, may then be added, as can higher melting active components or a suspension concentrate containing other active components.
Process of Manufacturing Surprislngly, it has been found that stable aqueous suspension concentrate compositions of pendlmethalin are prepared ~ith at least 4.0% o$ the pendimethalin in the orange crystal form, contrary to what has been reported prevlously. In the present invention pendimethalin even in the large orange crystal :: . . . . . .. . .
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Xanthan gum, guar gum; yum arabic and cellulose derivatives and the like are suitable for additlon in amounts of about 0~02~ to 3 %r on a weight to volume basis.
Preservatives to prevent microbial spoiling in the compositions of the invention are inclu~ed as necessary. One example is a 38% formaldehyde solution. Other preservatives include methyl or propyl parahydroxyhenzoate, 2-bromo-2-nitro-propane-1,3-diol, sodium benzoate, glutaraldehyde, o-phenylphenol, benziæothiazolinones, 5-chloro-2-methyl-4-i~othiazolin-3-one, pentachlorophenol, 2-4-dichlorobenzyalcohol~ or mixtures thereof and o~hers known to those in the art. Siliconic antifoaming agents are useful in the present compositions.
Ankifreezing agents such as ethylene glycol, propylene glycol, other glycols, glycerine or urea may be added to the aqueous suspension concentrate compositions. Additional surfactants, preservatives and thickening agents, such as clays, precipitated silicas, polyvinyl alcohol, polyvinyl-pyrrolidone, polyacrylamides and the like, may then be added, as can higher melting active components or a suspension concentrate containing other active components.
Process of Manufacturing Surprislngly, it has been found that stable aqueous suspension concentrate compositions of pendlmethalin are prepared ~ith at least 4.0% o$ the pendimethalin in the orange crystal form, contrary to what has been reported prevlously. In the present invention pendimethalin even in the large orange crystal :: . . . . . .. . .
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8 ~110~-7532 form may be used to formulate stable aqueous suspen5ions.
Further, up to 100% of khe pendimethalin may be present as the orange crystal form when preparlny the -ompositions o~ the invention, whereas only the yellow crystal form was favored to avoid large elongated crystals of formulates of pendimethalin.
Thus, aqueous suspension concentrate compositions of pendimethaline alone or in combination with a second hiyher melting pesticide(s) comprise on a weight to volume basis, about 5.0~ to 50.0~ of pendimethalin containing about 4.0% to 100% of the orange crystal form; about 0% to 50.0% of one or more secondary pesticide(s) having a melting point grea~er than 70C or being water soluble; about 3.0% to 30.0% coformulants as described hereinabove; and the remainder water to total the aomposition to 100%.
The aompositions of the present invention are readily prepared by adding solid pendimethalin to water that may contain some of the coformulants, such as the anti~oaming agents, and/or suspending agents; milling at ambient temperatures the resulting solid-aqueous to obtain an average particle size of less than 20 microns, preferably 2 microns to 10 microns; and then adding, if desired, other coformulants such as thickening agents, antifreezing agents, surfactants, dispersing agents, wetting agents, suspending agents and preservatlves.
The follo~ing examples ~urther illustrate the present invention and are not limitative thereof.
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Further, up to 100% of khe pendimethalin may be present as the orange crystal form when preparlny the -ompositions o~ the invention, whereas only the yellow crystal form was favored to avoid large elongated crystals of formulates of pendimethalin.
Thus, aqueous suspension concentrate compositions of pendimethaline alone or in combination with a second hiyher melting pesticide(s) comprise on a weight to volume basis, about 5.0~ to 50.0~ of pendimethalin containing about 4.0% to 100% of the orange crystal form; about 0% to 50.0% of one or more secondary pesticide(s) having a melting point grea~er than 70C or being water soluble; about 3.0% to 30.0% coformulants as described hereinabove; and the remainder water to total the aomposition to 100%.
The aompositions of the present invention are readily prepared by adding solid pendimethalin to water that may contain some of the coformulants, such as the anti~oaming agents, and/or suspending agents; milling at ambient temperatures the resulting solid-aqueous to obtain an average particle size of less than 20 microns, preferably 2 microns to 10 microns; and then adding, if desired, other coformulants such as thickening agents, antifreezing agents, surfactants, dispersing agents, wetting agents, suspending agents and preservatlves.
The follo~ing examples ~urther illustrate the present invention and are not limitative thereof.
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9 6110g-7532 Preparatlon of s~able agueou~Y .sus~ension concentrate compositions of pendimethalin An aqueous solution containing surfaatant(s) and antifoaming agents, and if desired, water soluble pesticides i5 prepared at ambient temperatures. Solid pendimethalin, having a minimum of 4% of the orange crystal form, is added, and any other solid second pesticide having a melting point greater than 70C
may also be added.
This is milled to achieve the desired average particle size of suspended particles of less than 20 microns, preferably less than 6 miarons (2 microns to 6 microns~. Then thickening agents, suspending agents, anti~reezing agents, preservatives and additional surfactants are admixed with the resulting mixture.
Finally, this resulting stable aqueous suspension concentrate composition is packaged.
Utilizing the above procedure yields the stable aqueous suspenJlon concentrate compositions listed in Table I.
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may also be added.
This is milled to achieve the desired average particle size of suspended particles of less than 20 microns, preferably less than 6 miarons (2 microns to 6 microns~. Then thickening agents, suspending agents, anti~reezing agents, preservatives and additional surfactants are admixed with the resulting mixture.
Finally, this resulting stable aqueous suspension concentrate composition is packaged.
Utilizing the above procedure yields the stable aqueous suspenJlon concentrate compositions listed in Table I.
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Claims (24)
1. An aqueous suspension concentrate composition comprising, on a weight to volume basis: about 5.0% to 50.0%
pendimethalin having 4% orange crystal form to 96% yellow crystal form to 100% orange crystal form; about 0% to 50.0% of one or more secondary pesticides having a melting point greater than 70°C or being water soluble; about 3.0% to 30.0% coformulants; and about 20.0% to 92.0% water.
pendimethalin having 4% orange crystal form to 96% yellow crystal form to 100% orange crystal form; about 0% to 50.0% of one or more secondary pesticides having a melting point greater than 70°C or being water soluble; about 3.0% to 30.0% coformulants; and about 20.0% to 92.0% water.
2. An aqueous suspension concentrate composition comprising, on a weight to volume basis: about 5.0% to 50.0% solid pendimethalin having 4% orange crystal form to 96% yellow crystal form to 100% orange crystal form; about 3.0% to 30.0% non-pesticidal coformulants; and about 20.0% to 92.0% water.
3. A composition according to claim 1 or 2, wherein said coformulants are surfactants, dispersing agents or wetting agents;
suspending agents; antifreezing agents; antifoaming agents;
thickening agents; and preservatives.
suspending agents; antifreezing agents; antifoaming agents;
thickening agents; and preservatives.
4. A composition according to claim 3, wherein said surfactants, dispersing agents or wetting agents are ethylene oxide/propylene oxide condensates; alkyl, aryl- and aryl, aryl-ethoxylates; lignosulfonates; cresol-formaldehyde condensates and sulfonates thereof; naphthalene-formaldehyde condensates and sulfonates thereof; polycarboxylates and derivatives; and mixtures thereof.
5. A composition according to claim 4, wherein said suspending agents are polysaccharide gums or cellulose derivatives.
6. A composition according to claim 5, wherein said polysaccharide gums are Xanthan gum, guar gum, gum arabic, and mixtures thereof.
7. A composition according to claim 6, wherein said antifreezing agents are ethylene glycol, propylene glycol, glycerine, urea, and mixtures thereof.
8. A composition according to claim 7, wherein said thickening agents are clays, precipitated silicas, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylamides, and mixtures thereof.
9. A composition according to claim 8, wherein said preservative is a 33% formaldehyde solution, methyl or propyl parahydroxybenzoate, 2-bromo-2-nitro-propane-1,3-diol, sodium benzoate, glutaraldehyde, 0-phenylphenol, benzisothiazolinones, 5-chloro-2-methyl-4-isothiazolin-3-one, pentachlorophenol, 2-4-dichlorobenzylalcohol, or mixtures thereof.
10. A composition according to claim 9, wherein said antifoaming agent is a siliconic antifoaming agent.
11. A composition according to claim 10, comprising, on a weight to volume basis: about 5.0% to 50.0% pendimethalin with 10%, on a weight to weight basis, of the orange crystal form;
about 0% to 50.0% one or more secondary pesticides having a melting point greater than 70°C or being water soluble; cresol-formaldehyde condensates and sulfonates thereof, naphthalene-formaldehyde condensates and sulfonates thereof, lignosulfonates, and mixtures thereof; about 0.05% to 2.5% Xanthan gum, guar gum, gum arabic, or cellulose derivatives; about 2.0% to 15.0% ethylene glycol, propylene glycol or urea; about 0.05% to 1.0% antifoaming agent; about 0.05% to 2.0% thickening agent; about 0.05% to 2.5%
preservative; and the remainder water to total said composition to 100%.
about 0% to 50.0% one or more secondary pesticides having a melting point greater than 70°C or being water soluble; cresol-formaldehyde condensates and sulfonates thereof, naphthalene-formaldehyde condensates and sulfonates thereof, lignosulfonates, and mixtures thereof; about 0.05% to 2.5% Xanthan gum, guar gum, gum arabic, or cellulose derivatives; about 2.0% to 15.0% ethylene glycol, propylene glycol or urea; about 0.05% to 1.0% antifoaming agent; about 0.05% to 2.0% thickening agent; about 0.05% to 2.5%
preservative; and the remainder water to total said composition to 100%.
12. A composition according to claim 11, wherein the said pesticide with melting point greater then 70°C is Isoproturon, [N,N-dimethyl-N'-(4-(1-methylethyl)-phenyl)-urea]; Linuron, [N-(3,4-dichlorophenyl)-N'-methoxy-N'-methyl urea]; Metoxuron, [N'-(3-chloro-4-methoxyphenyl)-N,N-dimethylurea]; Chlortoluron, [N'-(3-chloro-4-methylphenyl)-N,N-dimethylurea]; Atrazine, [2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine, terbutylazine, 2-tert-butylamino-4-chloro-6-ethylamino-1,3,5-triazine and metolachlor, 2-chloro-6'-ethyl-N-(2-methoxy-1-methylethyl)acet-o-toluidide; an Imidazolinone herbicide; 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid and water soluble salts thereof; and the isomeric mixture of methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-m-toluate and methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)toluate.
13. A composition according to claim 9, comprising, on a weight to volume basis: about 5.0% to 50.0% solid pendimethalin with 10%, on a weight to weight basis, of the orange crystal form;
about 2.0% to 20.0% cresol-formaldehyde condensates or sulfonates thereof, naphthalene-formaldehyde condensates or sulfonates thereof; lignosulfonates, or mixtures thereof; about 0.05% to 2.5%
Xanthan gum, guar gum, gum arabic, or cellulose derivatives; about 2.0% to 15.0% ethylene glycol, propylene glycol or urea; about 0.05% to 1.0% antifoaming agent; about 0.05% to 2.0% thickening agent; about 0.05% to 2.5% preservative; and the remainder water to total said composition to 100%.
about 2.0% to 20.0% cresol-formaldehyde condensates or sulfonates thereof, naphthalene-formaldehyde condensates or sulfonates thereof; lignosulfonates, or mixtures thereof; about 0.05% to 2.5%
Xanthan gum, guar gum, gum arabic, or cellulose derivatives; about 2.0% to 15.0% ethylene glycol, propylene glycol or urea; about 0.05% to 1.0% antifoaming agent; about 0.05% to 2.0% thickening agent; about 0.05% to 2.5% preservative; and the remainder water to total said composition to 100%.
14. A composition according to claim 12 or 13, comprising, on a weight to volume basis: about 20.0% to 40.0% pendimethalin;
about 3.0% to 5.0% sodium cresol-formaldehyde condensate or sodium cresol-formaldehyde sulphonated condensate; about 5% to 10%
ethylene glycol or urea; about 0.1% to 1.0% siliconic antifoaming agent; about 0.1% to 0.3% Xanthan gum; about 0.2% to 1.0% of a 38%
formaldehyde solution; and the balance water.
about 3.0% to 5.0% sodium cresol-formaldehyde condensate or sodium cresol-formaldehyde sulphonated condensate; about 5% to 10%
ethylene glycol or urea; about 0.1% to 1.0% siliconic antifoaming agent; about 0.1% to 0.3% Xanthan gum; about 0.2% to 1.0% of a 38%
formaldehyde solution; and the balance water.
15. A composition according to claim 14, comprising, on a weight to volume basis: 40.0% pendimethalin; 5.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% ethylene glycol; 0.5%
siliconic antifoaming agent; 0.2% Xanthan gum; 0.5% of a 38%
formaldehyde solution; and the balance water.
siliconic antifoaming agent; 0.2% Xanthan gum; 0.5% of a 38%
formaldehyde solution; and the balance water.
16 61109-7532 16. A composition according to claim 12, comprising, on a weight to volume basis: 27.3% pendimethalin; 18.2% atrazine, 3.4%
sodium cresol-formaldehyde sulphonated condensate; 5.8% urea;
1.34% polylkylene glycol ether and polyoxyethylene alkylaryl ether; 0.9% siliconic antifoaming agent; 0.2% Xanthan gum; 0.5% of a 38% formaldehyde solution; and the balance water.
sodium cresol-formaldehyde sulphonated condensate; 5.8% urea;
1.34% polylkylene glycol ether and polyoxyethylene alkylaryl ether; 0.9% siliconic antifoaming agent; 0.2% Xanthan gum; 0.5% of a 38% formaldehyde solution; and the balance water.
17. A composition according to claim 12, comprising, on a weight to volume basis, 23.6% pendimethalin; 23.6% isoproturon;
3.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% urea or ethylene glycol; 2.0% ethylene oxide-propylene oxide copolymer;
2.0% silica; 0.5% siliconic antifoaming agent; 0.1% Xanthan gum;
0.25% of a 38% formaldehyde solution; and the balance water.
3.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% urea or ethylene glycol; 2.0% ethylene oxide-propylene oxide copolymer;
2.0% silica; 0.5% siliconic antifoaming agent; 0.1% Xanthan gum;
0.25% of a 38% formaldehyde solution; and the balance water.
18. A composition according to claim 12, comprising, on a weight to volume basis: 30.0% pendimethalin; 5.0% of the water-soluble ammonium salt of 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid; 4.0% sodium lignosulphonate; 8.0% ethylene glycol, 0.5% siliconic antifoaming agent; 0.75% silica; 0.1% Xanthan gum; 0.25% of a 38% formaldehyde solution; and the balance water.
19. A composition according to claim 12, comprising, on a weight to volume basis. 20.0% pendimthalin; 30.0% chlortoluron;
3.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% urea or ethylene glycol; 2.0% ethylene oxide-propylene oxide copolymer;
0.5% siliconic antifoaming agent; 2.0% silica; 0.05% Xanthan gum;
3.0% sodium cresol-formaldehyde sulphonated condensate; 8.0% urea or ethylene glycol; 2.0% ethylene oxide-propylene oxide copolymer;
0.5% siliconic antifoaming agent; 2.0% silica; 0.05% Xanthan gum;
20.25% of a 38% formaldehyde solution; and the balance water.
20. A composition according to claim 12, comprising, on a weight to volume basis, 26.0% pendimethalin; 12.5% of an isomeric mixture of methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-m-toluate and methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-p-toluate; 3.0% sodium cresol-formaldehyde condensate; 1.3% triethanolamine salt of polyarylarylethoxylate phosphate; 6.0% alkylphenol-ethoxylate; 5.0% ethylene glycol; 0.4%
siliconic antifoaming agent; 2.0% silica; 0.1% Xanthan gum, 0.25%
of a 38% formaldehyde solution; and the balance water.
20. A composition according to claim 12, comprising, on a weight to volume basis, 26.0% pendimethalin; 12.5% of an isomeric mixture of methyl 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-m-toluate and methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-p-toluate; 3.0% sodium cresol-formaldehyde condensate; 1.3% triethanolamine salt of polyarylarylethoxylate phosphate; 6.0% alkylphenol-ethoxylate; 5.0% ethylene glycol; 0.4%
siliconic antifoaming agent; 2.0% silica; 0.1% Xanthan gum, 0.25%
of a 38% formaldehyde solution; and the balance water.
21. A method for the preparation of a stable aqueous suspension concentrate composition of pendimethalin, said method comprising: admixing, on a weight to volume basis, about 5.0% to 50.0% pendimethalin having 4% orange crystal form to 96% yellow crystal form to 100% orange crystal form; about 0% to 50.0% of one or more secondary pesticides having a melting point greater than 70°C or being water soluble in an aqueous solution containing surfactant(s), dispersing agent(s) or wetting agent(s) and antifoaming agents; milling the resulting mixture, wherein said average particle size of suspended particles is less than 20 microns; admixing thickening agents, suspending agents, antifreezing agents, preservatives and additional surfactants; and packaging the resulting aqueous suspension concentrate composition.
17a 61109-7532
17a 61109-7532
22. A method according to claim 21, wherein said orange crystal form is 10% orange crystal form to 90% yellow crystal form to 100% orange crystal form.
23. A method according to claim 22, wherein said suspended particle size is 2 microns to 10 microns.
24. A method according to claim 21, said composition comprising, on a weight to volume basis, about 5.0% to 50.0%
pendimethalin; about 0% to 50.0% said second higher melting or water soluble pesticide; about 2.0% to 20.0% of the surfactants cresol-formaldehyde condensates and sulfonates thereof, naphthalene formaldehyde condensates and sulfonates thereof, lignosulfonates, and mixtures thereof; about 0.05% to 2.5% of the suspending agent Xanthan gum, guar gum, gum arabic, or cellulose derivatives; about 2.0% to 15.0% of the antifreezing agents ethylene glycol, propylene glycol or urea; about 0.05% to 1.0%
antifoaming agent; about 0.05% to 2.0% thickening agent; about 0.05% to 2.5% preservative; and water to total said composition to 100%.
pendimethalin; about 0% to 50.0% said second higher melting or water soluble pesticide; about 2.0% to 20.0% of the surfactants cresol-formaldehyde condensates and sulfonates thereof, naphthalene formaldehyde condensates and sulfonates thereof, lignosulfonates, and mixtures thereof; about 0.05% to 2.5% of the suspending agent Xanthan gum, guar gum, gum arabic, or cellulose derivatives; about 2.0% to 15.0% of the antifreezing agents ethylene glycol, propylene glycol or urea; about 0.05% to 1.0%
antifoaming agent; about 0.05% to 2.0% thickening agent; about 0.05% to 2.5% preservative; and water to total said composition to 100%.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86710686A | 1986-05-23 | 1986-05-23 | |
| US06/866,864 | 1986-05-23 | ||
| US06/867,106 | 1986-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1287570C true CA1287570C (en) | 1991-08-13 |
Family
ID=25349099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000537637A Expired - Fee Related CA1287570C (en) | 1986-05-23 | 1987-05-21 | Aqueous suspension concentrate compositions of pendimethalin |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4871392A (en) |
| EP (1) | EP0249770B1 (en) |
| JP (1) | JP2894608B2 (en) |
| KR (1) | KR950006919B1 (en) |
| AR (1) | AR245565A1 (en) |
| AT (1) | ATE92251T1 (en) |
| BR (1) | BR8702667A (en) |
| CA (1) | CA1287570C (en) |
| DD (2) | DD261081A5 (en) |
| DE (1) | DE3786845T2 (en) |
| DK (1) | DK173947B1 (en) |
| ES (1) | ES2059322T3 (en) |
| FI (1) | FI90187C (en) |
| GR (1) | GR3008658T3 (en) |
| HK (1) | HK1001038A1 (en) |
| HU (1) | HU204654B (en) |
| IE (1) | IE63343B1 (en) |
| IL (1) | IL82642A (en) |
| NZ (1) | NZ220424A (en) |
| SK (1) | SK394887A3 (en) |
| YU (1) | YU47262B (en) |
| ZA (1) | ZA873749B (en) |
| ZW (1) | ZW9587A1 (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4810279A (en) * | 1987-01-27 | 1989-03-07 | American Cyanamid Company | Herbicidal oil in water combination compositions of pendimethalin |
| US5250502A (en) * | 1990-04-30 | 1993-10-05 | American Cyanamid Company | Method for enhancing the herbicidal activity of formulations containing solid imidazolinyl benzoic acid esters with bisulfate |
| EP0473890A1 (en) * | 1990-08-28 | 1992-03-11 | American Cyanamid Company | Aqueous herbicidal compositions of 2-(2-imidazolin-2-yl)-pyridines and quinolines |
| US5496845A (en) * | 1994-05-25 | 1996-03-05 | American Cyanamid Co. | Suspension concentrate compositions of arylpyrrole insecticidal and acaricidal agents |
| US5750130A (en) * | 1995-02-07 | 1998-05-12 | Ferrell; Paul | Presticide compositions |
| US6242613B1 (en) | 1996-08-02 | 2001-06-05 | American Cyanamid Co. | Stable arylpyrrole particles, process for their preparation and suspension concentrate compositions comprising them |
| CZ293077B6 (en) * | 1996-08-02 | 2004-02-18 | American Cyanamid Company | Stable arylpyrrole particles, process of their preparation and compositions formed by a suspension concentrate containing such particles |
| GB9720061D0 (en) | 1997-09-19 | 1997-11-19 | Crosfield Joseph & Sons | Metal compounds as phosphate binders |
| GB9817354D0 (en) * | 1998-08-11 | 1998-10-07 | Agrevo Env Health Ltd | Liquid formulation |
| DE60105174T2 (en) | 2000-08-25 | 2005-01-13 | Basf Ag | CONTINUOUS PROCESS FOR THE PREPARATION OF A HERBICIDAL AQUEOUS SUSPENSION CONCENTRATE |
| EA008340B1 (en) | 2003-04-14 | 2007-04-27 | Басф Акциенгезельшафт | An aqueous, flowable concentrate composition of pendimethalin |
| MY157620A (en) | 2006-01-31 | 2016-06-30 | Cytochroma Dev Inc | A granular material of a solid water-soluble mixed metal compound capable of binding phosphate |
| GB0714670D0 (en) | 2007-07-27 | 2007-09-05 | Ineos Healthcare Ltd | Use |
| GB0720220D0 (en) | 2007-10-16 | 2007-11-28 | Ineos Healthcare Ltd | Compound |
| PL2346326T3 (en) * | 2008-10-14 | 2014-08-29 | Basf Se | Crystalline complexes of pendimethalin and metazachlor |
| GB0913525D0 (en) | 2009-08-03 | 2009-09-16 | Ineos Healthcare Ltd | Method |
| US9288979B2 (en) * | 2010-02-03 | 2016-03-22 | United Phosphorus Limited | Microencapsulated pendimethalin comprising alkali or alkaline earth metal salt of organic acid |
| GB201001779D0 (en) | 2010-02-04 | 2010-03-24 | Ineos Healthcare Ltd | Composition |
| BR112013011844B1 (en) * | 2010-11-12 | 2018-11-06 | Rhodia Operations | agricultural pesticide compositions |
| CN102187862B (en) * | 2010-11-22 | 2013-08-21 | 南通联农农药制剂研究开发有限公司 | Pesticide composition containing pendimethalin and preparation method thereof |
| PE20141483A1 (en) | 2011-08-10 | 2014-11-16 | Upl Ltd | IMPROVED HERBICIDE FORMULATION |
| JP2015522560A (en) * | 2012-06-06 | 2015-08-06 | ダウ アグロサイエンシィズ エルエルシー | Strong herbicidal suspension |
| JPWO2022118820A1 (en) * | 2020-12-01 | 2022-06-09 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4077795A (en) * | 1972-08-22 | 1978-03-07 | Union Carbide Corporation | Method for inhibiting the growth of tobacco suckers |
| US3948636A (en) * | 1972-11-09 | 1976-04-06 | Diamond Shamrock Corporation | Flowable aqueous composition of water-insoluble pesticide |
| US4188202A (en) * | 1975-11-12 | 1980-02-12 | Fisons Limited | Composition |
| JPS52156922A (en) * | 1976-06-23 | 1977-12-27 | Kumiai Chem Ind Co Ltd | Killing of weeds in lawn |
| US4082537A (en) * | 1977-03-23 | 1978-04-04 | American Cyanamid Company | 2,6-dinitroaniline herbicidal compositions |
| US4266965A (en) * | 1979-10-29 | 1981-05-12 | Stauffer Chemical Company | 2-(α-naphthoxy)-N,N-diethyl propionamide as an aqueous flowable concentrate |
| JPS56150003A (en) * | 1980-03-13 | 1981-11-20 | American Cyanamid Co | Herbicidal method and composition |
| DE3302648A1 (en) * | 1983-01-27 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | PLANT PROTECTION AGENT IN THE FORM OF MIXED DISPERSIONS |
| EP0163598B1 (en) * | 1984-04-27 | 1989-10-04 | Ciba-Geigy Ag | Herbicidal compositions |
| DE3503706A1 (en) * | 1985-02-04 | 1986-08-07 | Ciba-Geigy GmbH, 7867 Wehr | FLOWABLE HERBICIDE AGENT |
-
1987
- 1987-05-07 US US07/045,457 patent/US4871392A/en not_active Expired - Lifetime
- 1987-05-21 CA CA000537637A patent/CA1287570C/en not_active Expired - Fee Related
- 1987-05-22 IE IE134587A patent/IE63343B1/en not_active IP Right Cessation
- 1987-05-22 DE DE87107496T patent/DE3786845T2/en not_active Expired - Lifetime
- 1987-05-22 DD DD87303039A patent/DD261081A5/en not_active IP Right Cessation
- 1987-05-22 EP EP87107496A patent/EP0249770B1/en not_active Expired - Lifetime
- 1987-05-22 ES ES87107496T patent/ES2059322T3/en not_active Expired - Lifetime
- 1987-05-22 DK DK198702611A patent/DK173947B1/en active IP Right Grant
- 1987-05-22 AT AT87107496T patent/ATE92251T1/en not_active IP Right Cessation
- 1987-05-23 KR KR1019870005176A patent/KR950006919B1/en not_active IP Right Cessation
- 1987-05-23 JP JP62126841A patent/JP2894608B2/en not_active Expired - Lifetime
- 1987-05-24 IL IL82642A patent/IL82642A/en unknown
- 1987-05-25 ZA ZA873749A patent/ZA873749B/en unknown
- 1987-05-25 FI FI872295A patent/FI90187C/en not_active IP Right Cessation
- 1987-05-25 DD DD87303108A patent/DD256822A5/en unknown
- 1987-05-25 HU HU872333A patent/HU204654B/en unknown
- 1987-05-25 YU YU93787A patent/YU47262B/en unknown
- 1987-05-25 BR BR8702667A patent/BR8702667A/en active Search and Examination
- 1987-05-25 NZ NZ220424A patent/NZ220424A/en unknown
- 1987-05-26 ZW ZW95/87A patent/ZW9587A1/en unknown
- 1987-05-26 AR AR87307657A patent/AR245565A1/en active
- 1987-05-29 SK SK3948-87A patent/SK394887A3/en unknown
-
1993
- 1993-08-05 GR GR930400655T patent/GR3008658T3/el unknown
-
1998
- 1998-01-05 HK HK98100063A patent/HK1001038A1/en not_active IP Right Cessation
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