IE44883B1 - Herbicidal compositions - Google Patents
Herbicidal compositionsInfo
- Publication number
- IE44883B1 IE44883B1 IE357/77A IE35777A IE44883B1 IE 44883 B1 IE44883 B1 IE 44883B1 IE 357/77 A IE357/77 A IE 357/77A IE 35777 A IE35777 A IE 35777A IE 44883 B1 IE44883 B1 IE 44883B1
- Authority
- IE
- Ireland
- Prior art keywords
- composition
- bipyridylium
- pyrimidine
- triazolo
- herbicidal
- Prior art date
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Organic Chemistry (AREA)
- Hospice & Palliative Care (AREA)
- Animal Behavior & Ethology (AREA)
- Otolaryngology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Herbicidal composition which represents a reduced health hazard and which contains, as active ingredient, a salt of a herbicidal quaternary dipyridylium cation in combination with an s-triazolo[1,5-a]pyrimidine derivative, which makes the composition act as an emetic.
Description
This invention relates to herbicidal compositions containing a herbicidal bipyridylium quaternary salt as an active ingredient.
Over the years, a wide range of pesticides has been 5 developed for agricultural use in the control of fungal and insect pests and weeds. While these substances are necessarily toxic to certain forms of life, when used, with due care and in accordance with governmentally approved codes of practice, they present no hazard to human life. However, in spite of efforts to encourage those concerned with pesticides to adopt safe handling practices, instances of misuse of pesticides do occur. One particular unsafe practice in the case of liquid pesticides is for an operator to transfer a small amount of the concentrated pesticide to a domestic container such as a beverage bottle for subsequent use at home. The risk attached to this practice is of course that a child or incautious adult coming upon the bottle may swallow the contents with possibly serious consequences.
We have now found it possible to reduce the likelihood of serious consequences of such accidental swallowing by induction of emesis. This can result in some cases in the rapid removal of the pesticidal composition from the stomach and digestive tract- pefore lethal amounts of the pesticide can be assimilated by the body.
We have further discovered that the admixture of a known triazolo Zl,5-a./7 pyrimidine derivative of formula (I), as specified hereinafter, to a herbicidal bipyridylium quaternary salt in a herbicidal composition produces a composition which if swallowed tends to induce emesis, and thereby, expulsion of the composition.
According to the invention there is provided a herbicidal composition of reduced health hazard comprising a salt of a herbicidal bipyridylium quaternary cation and a βίο triazolo /“l,5-a_7 pyrimidine derivative of the formula:Y
wherein R^ is an amino, alkylamino, phenylalkylamino, dialkylamino, ureido, carboxyl, hydroxyalkyl or carbazoyl
3 group; R is an alkyl, cycloalkyl or alkenyl group; R is hydrogen, halogen or an alkyl or hydroxyalkyl group; one of x and ¥ stands for an oxo or thioxo radical, and the other of X and Y stands for hydrogen or an alkyl radical and when X stands for an oxo or thioxo radical, the nucleus contains a double bond between the carbon atoms in positions 6 and 7, and when ¥ stands for an oxo or thioxo radical, the nucleus contains a double bond between the carbon atoms in positions 5 and 6; or a base addition salt of a triazolo-pyrimidine derivative as defined above which contains an acidic group; or, an acylated derivative, or base addition salt thereof.
Preferably the invention provides a herbicidal composition of reduced health hazard comprising a salt of a herbicidal bipyridylium quaternary cation and a s-triazolo/7l,5-a^7 pyrimidine derivative of the formula:-
NHK wherein R^ is hydrogen, a alkyl radical, or a COOEt 2 radical, R is a alkyl radical or an allyl radical, and
R is a C^_4 alkyl radical; and addition salts thereof. The s-triazolo /71/5-aJ7 pyrimidine ring structure is numbered as shown below:-,.'
Particular derivatives of, 5-oxo-4,5-dihydro-s-triazolo 15 Z~l,5-a_/ pyrimidine of use -in the practice of the invention are:··
- 4 ^4883
6-methyl-4-n-propyl-2-n-propylamino2-amino-6-methyl-4-allyl2-amino-4,6-di-n-propyl2-ethoxycarbonylamino-5-methyl-4-n-propyl5 An especially useful triazolo-pyrimidine for use in the compositions of the invention is 2-amino-6-methyl-5-oxo-4-npropyl-4,5-dihydro-s-triazolo Z”l,5-a_7 pyrimidine (II).
ch3
NH2 n-Pr (II)
Preferred herbicidal bipyridylium quaternary salts for use in the compositions of the invention are those of the following formulae:-
or wherein R and R which may be the same or different, stand
44883 .for alkyl radicals of from 1 to 4. carbon atoms which may be substituted by hydroxyl, halogen, carboxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, carbamoyl or N-substituted carbamoyl; /“xJ7 n represents an anion and n is an integer from 1 to 4 inclusive. ;
Particularly preferred herbicidal bipyridylium -quaternary salts are those listed below: 1,I-dimethyl-4,4'-bipyridylium di(methyIsulphate) (paraquat dimethosulphate)
1,1'-ethylene-2,2'-bipyridylium dibromide (diquat dibromide.) 1,1'-dimethyl-4,4'-bipyridylium d chloride (paraquat dichloride) l,l'-di-2-hydroxyethyT-4,4'-bipyr .dylium dichloride
1-(2-hydroxyethyl5-1’-methyl-4,; 4' - bipyridylium dichloride l,l'-di-carbamoylmethyl-4,4'-bipyi idylium dichloride 1,11-bis-N,N-dimethylcarbamoylmett yl-4,41-bipyridylium dichloride
1,1’-dimethyl-^,4'-bipyridylium stlphate (paraquat sulphate) 1,1'-bis-N,ϊϊ-diethylcarbamQylmeth’ 1-4,4'-bipyridylium dichloride .- .
-1,1'-diacetonyl-4,4 '-bipyridylium dichloride
1,1’-diethoxycarbonyImethy1-4,4'-i ipyridylium dibromide
The names in brackets alongsi de some of the compounds
- 6 -.4*8 8 3 in the above list are the accepted common names for these compounds. Thus 'paraquat' is the common name for the 1,1'dimethyl-4,4'-bipyridylium cation. Paraquat is a particularly preferred bipyridylium cation for use in the compositions of the invention. A particularly preferred anion Z7x-7 n” is the chloride anion, for reasons of convenience and economy, but any anion which gives rise to a conveniently watersoluble salt may be used if desired. The herbicidal action is due solely to the cation and for this reason the concentration of a herbicidal bipyridylium salt composition is frequently given in terms of the cation alone. The amount of herbicidal bipyridylium quaternary salt present in the compositions of the invention is generally from 1.0 to 99.9%. by weight.
The compositions of the invention may comprise a carrier or diluent, and may be solids, e.g. granules, or liquids, e.g. aqueous solutions.
In a preferred aspect the invention provides a concentrated herbicidal composition comprising an aqueous solution of a salt of a herbicidal bipyridylium quaternary cation and a triazolo-pyrimidine as hereinbefore defined. Preferably the herbicidal bipyridylium quaternary cation is paraquat.
The amount of herbicidal bipyridylium quaternary cation present in tne aqueous solution is preferably from 0.5 to 4.0 pounds per Imperial gallon (50 grams to 400 grams per litre).
S3
Preferably the composition also comprises a surface active agent.
Surface-active agents may be cationic, non-ionic or anionic. Generally speaking cationic and non-ionic surface5 active agents are preferred to anionic surface-active agents 7for use: in the compositions of the invention, since the latter may -interact undesirably with the bipyridylium quaternary salt in the compositions. Examples of non-ionic surface-active agents for use in the compositions of the invention Include the condensation products of ethylene oxide with alkyl phenols such as octylphenol, nonylphenol and octylcresol. Other non-ionic agents are the partial esters. derived from long chain fatty acids and hexitol anhydrides, for example sorbitan monolaurate? the conden15 sation. products of the said partial esters with ethylene oxide? and the lecithins. Examples of cationic surfaceactive agents include quaternary salts and condensates of ethylene, oxide with amines, for. example the substances sold under the Trade Mark Ethomeen, Ethoduomeen, Duoquad.
and Arquad.
Particularly preferred surface-active agents are the combinations of surface-active agents described in British Patent Specification Ho·. 998,2^64 for use in formulations of herbicidal bipyridylium quaternary salts.
The preparation of the triazolo-pyrimidines (I) has been described in Patent Specification No. 33549.
The emetic properties of the composition are primarily determined by the amount of triazolo-pyrimidine it contains.
In deciding the most appropriate amounts of triazolo-pyrimidine to use in any composition, regard must be had to the efficacy of the triazolo-pyrimidine relative to the toxicity of the herbicide. The amount of triazolo-pyrimidine to be included is preferably such that any sample of the composition containing a potentially lethal dose of herbicide will contain sufficient of the triazolo-pyrimidine to give it an emetic action. However, clearly neither lethal doses nor emetic doses can be directly measured in man; they can only be inferred from animal data.
Compositions according to the invention preferably contain from 0.1 to. 5 parts by weight of the triazolopyrimidine (e.g. the triazolopyrimidine II) per 100 parts of the herbicidal bipyridylium quaternary cation (e.g. paraquat). Conveniently the amount of the triazolo-pyrimidine (e.g. the triazolopyrimidine II) used is 0.25 to 2.0 parts per 100 parts of herbicidal bipyridylium quaternary cation (e.g.
paraquat).
Concentrated aqueous formulations of the invention are corrosive. They must be handled with care, to avoid splashing of the eyes or skin, and they should not be allowed to come
into contact with corrodeable metals prior to dilution.
The compositions according to the invention may also comprise coloured dyestuff or pigment compounds to give them a characteristic or distinguishing colour. Examples of such compounds are Monastral Blue BNV Paste and Lissamine
Turquoise VN 150.
The compositions according to the invention may also . comprise a stenching agent. Examples of such stenching ' agents ares alkyl pyridines as described.in ' ' Patent 10 Specification No. 37415 n-valeric acid; and tetrahydrothiophen.
If desired, the triazolo-pyrimidines (I) may be incorporated in thixotropic formulations of herbicidal quaternary salts. In particular the triazolo-pyrimidines (I) maybe . incorporated in the formulations of herbicidal bipyridylium 15 quaternary salts described in Patent
Specification No. 36536 These formulations comprise an aqueous solution of a herbicidal bipyridylium quaternary salt containing a gelling agent, for example finely divided silica, or a combination of the xanthan gum sold under, the Trade Mark
Kelzan with sodium metaborate. Xanthan gunt is a complex polysaccharide.
The compositions according to the invention may also comprise a herbicide other than a herbicidal bipyridylium
J 88 3 quaternary salt as hereinbefore defined. Examples of such herbicides ares
Amides (e.g. Ν,Ν-diallylchloroacetamide, 3,4-dichloropropion anilide, N-(3-chloro-4-methyl-phenyl)-2-methylpentamide).
Carbamates (e.g. Isopropyl-N-phenylcarbamate, isopropyl-N(3-chlorophenyl) carbamate, 4-chloro-2 but-2-ynyl-N-(3chlorophenvl) carbamate, 2-chlorallyl-N,N-diethyl-dithiocarbamate).
Ureas/anilides (e.g. N,N'-di-(2,2,2-trichloro-l-hydroxy10 ethyl)urea, 3,4-dichloroacetanilide, O-chloroisobutyranilide a-bromo-3,4-dichloroacetanilide, 3,4-dichloroformanilide, 2acetamido-3-chlqrotoluene).
Diazines (e.g. 3,4,5,6-tetrahydro-3,5-dimethyl-2-thio-2H1,3,5-thiadiazine, 5-bromo-3-isopropyl-6-methyluracil, 515 amino-4-chloro-2-phenyl-3-pyridazone, 1,2,3,6-tetrahydro3,6-dioxopyridaz ine).
Triazines (e.g. 2-chloro-4,6-bisethylamino-l,3,5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-l,3,5-triazine, 2chloro-4,6-bisisopropylamino-l,3,5-triazine, 4-ethylamino-620 isopropylamino-2-methoxy-l,3,5-triazine, 4,6-bisisopropylamino-2-methoxy-l,3,5-triazine).
44βθ3
The inclusion of the triazolo-pyrimidine (I) in compositions according to the invention has no significant adverse effect upon the herbicidal activity of the compositions.
The invention is illustrated by the following Examples.
EXAMPLE 1
This Example illustrates a composition according to the invention which comprises 2-amino-6-methyl-5-oxo-4-npropyl-4,5-dihydro-s-triazolo L”l.,5-a_7 pyrimidine (II) in . aqueous solution.
Ingredients % w/v
Paraquat concentrate x (II) 0.05
Water ' to 100 ml (where x gives 200 + 5 g/litre paraquat cation)
Paraquat concentrate is a solution of paraquat dichloride containing 25% to 30% fay weight of 1,11-dimethyl-4,4*- . bipyridylium cation. The amount used was chosen to give a composition containing 20% weight/volume paraquat cation.
The composition was prepared hy simple agitation of the ingredients together.
Λ 8 8 3
EXAMPLE 2
This Example illustrates a composition according to the invention which comprises the triazolo-pyrimidine (II) in aqueous solution. The composition comprises the following ingredients.
Ingredients
Paraquat concentrate
Sodium metaborate
Sodium benzoate Lissapol NX DS 4392
Silcolapse 5000 .
(II)
Water (where x gives 200 + 5 % w/v x
1.3
2.0
1.1
4.1
0.06
0.05 to 100 ml g/litre paraquat cation)
Lissapol NX is a Trade Mark for a surface-active agent comprising a condensate of from 7 to 8 molar proportions of ethylene oxide with 1 molar proportion of £nonylphenol.
DS 4392 is a code number for a surface-active agent comprising a mixture of amines derived from soya bean fatty acids condensed with approximately 15 molar proportions of ethylene oxide.
,44883
Silcolapse is a Trade Mark for an anti-foaming agent comprising a silicone derivative.
The composition described above was prepared by Simple agitation of the ingredients together.
EXAMPLE 3
This Example’ illustrates a composition according to the invention which comprises a gelling agent in addition to the triazolo-pyrimidine (XI). The composition comprises the following ingredients.
Ingredients Paraquat concentrate
Kelzan
Sodium metaborate Lissapol NX
DS 4392 (II)
Amount in Grams • x
0.4- (added as IS solution in water)
0.014
1.1
4.1
0.05 ilcolapse 5000
0.01 to 100 ml vhere x gives 200 + 5 g/litre
The composition described above was prepared by simple 20 agitation of the ingredients together and was sufficiently fluid when prepared to be poured-into containers. On
4-188 3 standing for 15 to 20 minutes the composition formed a gel and was not pourable unless vigorously shaken.
EXAMPLE 4
This Example illustrates a dry free flowing granular composition which is both stable in storage and is readily convertible into an aqueous solution for application as a spray.
A solution was made up having the following composition in which percentages are by weight.
Paraquat dichloride 33.0 10 2-amino-6-methyIr 5-oxo-4-n-propy1- 4,5-dihydro-s-triazolo Z”l,5-a_7 pyrimidine (II) 0.1 Sodium metaborate 2.5 Potassium phosphate 1.6 15 Lissapol NX 24.0 Water 38.8
100
310 gms of the above solution were then added in a thin stream to 690 gms of dried magnesium sulphate contained in the bowl of a HOBART C.E. 100 dough mixer (HOBART is a
Trade Mark). The resulting product which was dry was then 44883 passed through a granulating machine and finally agitated in a sieve having 30 meshes per linear inch to remove dust.
The resulting granules had a size of at least 0.3 mm and possessed a solution rate of 150 seconds.
EXAMPLE 5
This Example illustrates a composition according to the invention which comprises 2-amino-6-methyl-5-oxo-4-npropyl-4,5-dihydro-s-triazolo Z71>5-a_7 pyrimidine (II) and a stenching agent in aqueous solution.
Ingredients _ - % w/v
Paraquat concentrate x n-valeric acid 1.0
II 0.05
DS 4392 . 4.0
Silcolapse 0.01
Lissapol NX 1.0
Water to 100 mis (where x gives 200 g/1 paraquat ion).
The composition described above was prepared by Simple agitation of the ingredients together.
*4883
EXAMPLE 6
This Example illusti'ates a composition according to the invention which comprises 2-amino-6-methyl-5-oxo-4-npropyl-4,5-dihydro-s-triazolo fi.,5-af pyrimidine (II) in a thickened, coloured, aqueous solution.
Ingredients % w/v
Paraquat concentrate x
Synperonic 2 2.5
Synperonic 16 2.5
Nansa 1106 8.5
Monastral BNVS Paste 1.0
Pyridine Base · 1.0
II 0.05
Water to 100 mis (where x gives 200 g/1 paraquat ion).
Synperonic and Nansa are Trade Marks. Synperonic 2 is a condensation product of a mixture of 67% and 33%
C15 aliphatic alcohols with two equivalents of ethylene oxide. Synperonic 16 is a condensation product of a mixture of 67% C13 and 33% C15 aliphatic alcohols with sixteen equivalents of ethylene oxide. Nansa 1106 is sodium dodecyl (substantially C12 straight chain) benzene sulphonate. Monastral BNVS paste is a dispersion comprising 15% w/v copper phthalocyanine pigment in water. Pyridine base is a mixture consisting substantially of alkyl pyridines.
EXAMPLE 7
This Example illustrates-a composition according to the
Invention which comprises 2-amino-6-methyl-5-oxo-4-npropyl-4,5-dihydro-s-triazolo Z7l,5-a_7 pyrimidine (II) in aqueous solution.
Ingredients % w/v diquat dibromide x sodium, molybdate 0.18 potassium phosphate (as a mixture of dipotassium hydrogen . phosphate and potassium dihydrogen phosphate) 2.75 (II) 0.05 water to 100 ml (where x gives 140 + 5 g/1 diquat- ion).
Diquat ion is l/l'-ethylene-l^'-bipyridylium cation. The composition described above was prepared by simple agitation of the ingredients together, and had a pH of 5.5+ 0.3.
448S3
EXAMPLE 8
This Example illustrates a composition according to the invention which comprises 2-amino-6-methyl-5-oxo-4-npropyl-4,5-dihydro-s-triazolo Zl,5-a_7 pyrimidine (II) in aqueous solution.
Ingredients
Morfamquat dichloride
II water (where X gives 300 + 5 % w/v
X
0.05 to 100 mis g/1 morfamquat ion).
Morfamquat ion is l,l'-bis(3,5-dimethylmorpholinocarbonyImethyl)-4,4'-bipyridylium ion. The composition described above was prepared by simple agitation of the ingredients together.
EXAMPLE 9
This Example illustrates a composition according to the 15 invention which comprises 2-amino-6-methyl-5-oxo-4-npropyl-4,5-dihydro-s-tria2olo Z71,5-a_7 pyrimidine (II) in aqueous solution.
% w/v
448 8 3
Ingredients
I,11-bis(diethylcarbamoylinethyl) ' 4,4'-bipyridylium dichloride x
Tween 20 8 (II) 0.05 water to 100 ml . (where x gives 200 + 5 g/1 1,1'-bis(diethylcarbamoylinethyl)4,4'-bipyridylium ion).- The composition described above was prepared by simple· agitation of the ingredients together.
Tween is a Trade Mark. Tween 20 is a- condensation product of one mole of sorbitan monolaurate with twenty moles of ethylene oxide.
. EXAMPLE 10
This Example illustrates a composition according to the invention which comprises 2-n-propylamino-6-methyl-5-oxo-415 n-propyl-4,5-dihydro-s-triazolo /7lr5-a_7 pyrimidine in aqueous solution.
Ingredients % w/v
Paraquat concentrate x
2-n-propylamino-6-methyl-5-oxo-4-n20 propyl-4,5-dihydro-s-triazolo
Z7l/5_a_7 pyrimidine 0.05
Water to 100 ml (where x gives 200 + 5 g/litre paraquat cation)
- 20 4*8 «3
EXAMPLE 11
This Example illustrates a composition according to the invention which comprises 2-amino-5-oxo-4,6-di-n-propyl-4,5dihydro-s-triazolo £Ί,5-&Ν7 pyrimidine in aqueous solution.
Ingredients % w/v
Paraquat concentrate x
2-amino-5-oxo-4,6-di-n-propyl-4,5dihydro-s-triazolo Z7l,5-a_7pyrimidine 0.05
Water to 100 ml (where x gives 200 + 5 g/litre paraquat cation)
EXAMPLE 12
This Example illustrates a composition according to the invention which comprises 2-ethoxyearbonylamino-6-methyl-5~ oxo-4-n-propyl-4,5-dihydro-s-triazolo /7l/5-a_7 pyrimidine in aqueous solution.
Ingredients % w/v
Paraquat concentrate x
2-ethoxycarbonylamino-6-methy1-5oxo-4-n-propyl-4,5-dihydros-triazolo /Tl,5-aJ7 pyrimidine 0.05
Water to 100 ml (where x gives 200 + 5 g/litre paraquat cation)
EXAMPLE 13
Λ48 8 3
This Example illustrates a composition according to the invention which comprises 2-amino-6-methyl-5-oxo-4-allyl4,5-dihydro-s-triazolo Z7V5-a_7 pyrimidine in aqueous solution.
Ingredients % w/v
Paraquat concentrate x
2-amino-6-methyl-5-oxo-4-allyl-4,5dihydro-s-triazolo Z7l,5-a_7pyrimidlne 0.05
Water 'to 100 ml (where x gives 2.00 + 5 g/litre paraquat cation)
Claims (7)
1. CLAIMS:1. A herbicidal composition comprising a salt of a herbicidal bipyridylium quaternary cation and a s-trlazolo zfl,5-a_7 pyrimidine derivative of the formula:Y wherein R 1 is an amino, alkylamino, phenylalkylamino, dlalkylamino, ureido, carboxyl, hydroxyalkyl or carbazoyl 2. 3 group; R is an alkyl, cycloalkyl or alkenyl group; R is hydrogen, halogen or an alkyl or hydroxyalkyl group; one of X and. Y stands for an oxo or thioxo radical, and the other of X and Y stands for hydrogen or an alkyl radical and when X stands for an oxo or thioxo radical, the nucleus contains a double bond between the carbon atoms in positions 6 and 7, and when Y stands for an oxo or thioxo radical, the nucleus contains a double bond between the carbon atoms in positions 5 and 6; or a base addition salt of a triazolo-pyrimidine derivative as defined above which contains an acidic group; or an acylated derivative, or base addition salt thereof. - 23 44883
2. A composition as claimed in Claim 1, in which the salt of the herbicidal bipyridylium cation is a compound of the formula:- - wherein R and r\ which may be the same or different, Stand for alkyl radicals of from 1 to 4 carbon atoms Which may be substituted by hydroxyl, halogen, carboxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, carbamoyl or N10 substituted carbamoyl? C&f n_ represents an anion and n is an integer from 1 to 4 inclusive.
3. A composition as claimed in Claim 1 or 2 in which the salt of the herbicidal bipyridylium quaternary cation is 1,1-dimethy1-4,4'-bipyridylium dl(methylsulphate). 15 4. A composition as claimed in Claim 1 or 2 in which the salt of the herbicidal bipyridylium quaternary cation . is 1,1'-ethylene-2,2*-bipyridylium dibromide. - 24 44883 5. A composition as claimed in Claim 1 or 2 in which the salt of the herbicidal bipyridylium quaternary cation is 1,1*-dimethyl-4,4'-bipyridylium dichloride. 6. A composition as claimed in Claim 1 or 2 in which the 5 salt of the herbicidal bipyridylium quaternary cation is l,l'-di-2-hydroxyethy1-4,4'-bipyridylium dichloride. 7. A composition as claimed in Claim 1 or 2 in which the salt of the herbicidal bipyridylium quaternary cation is 1- (2-hydroxyethyl) -1' -methyl'-4,4' -bipyridylium 10 dichloride. 8. A composition as claimed in Claim 1 or 2 in which the salt of the herbicidal bipyridylium quaternary cation is 1,1'-di-carbamoyImethy1-4,4'-bipyridylium dichloride. 9. A composition as claimed in Claim 1 or 2 in which the · 15 salt of the herbicidal bipyridylium quaternary cation is l,l'-bis-N,N-dimethylcarbamoyImethy1-4,4'-bipyridylium dichloride. 10. A composition as claimed in Claim 1 or 2 in which the salt of the herbicidal bipyridylium quaternary cation 2o is 1,1'-dimethyl-4,4'-bipyridylium sulphate. 11. A composition as claimed in Claim 1 or 2 in which the salt of the herbicidal bipyridylium quaternary cation is l,l'-bis-N,N-diethylcarbamoylmethyl-4,4'-bipyridylium dichloride. 5 12. A composition as claimed in Claim 1 or 2 in which the salt of the herbicidal bipyridylium quaternary cation is 1,I 1 -diacetony1-4,4'-bipyridylium dichloride. 13. A composition as claimed.in Claim Ϊ or 2 in which the salt of the herbicidal bipyridylium quaternary cation 10 is 1,1'-diethoxycarbonylmethy1-4,4'-bipyridylium dibromide. 14. A. composition as claimed in any of the preceding claims in which the s-triazolo Z7l,5-aJ7 pyrimidine is a compound of the formulas15 wherein R 1 is hydrogen or a C^-alkyl radical, or a 2 COOEt radical, R is a C^_ 4 -alkyl radical, or an allyl 3 radical, and R is a C^_ 4 -alkyl radical. 4 4 S 8 3 15. A composition as claimed in any one of claims 1 to 14 in which the s-triazolo Z71,5-aJ7 pyrimidine is 2amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo ^l,5-a_7 pyrimidine. 5 16. A composition as claimed in any one of claims 1 to 14 in which the s-triazolo Z”l,5-a_7 pyrimidine is 6methyl-5-oxo-4-n-propyl-2-n-propylamino-4,5-dihydro-striazolo Z71,5-a_7 pyrimidine. 17. A composition as claimed in any one of claims 1 to 14 10 in which the s-triazolo /7l,5~aJ7 pyrimidine is 4allyl-2-amino-6-methyl-5-oxo-4,5-dihydro-s-triazolo £~l,5-a/7 pyrimidine. 18. A composition as claimed in any one of claims 1 to 14 in which the s-triazolo /71,5-a_7 pyrimidine is 215 amino-4,6-di-n-propyl-5-oxo-4,5-dihydro-s-triazolo /71,5-a_7 pyrimidine. 19. A composition as claimed in any one of claims 1 to 14 in which the s-triazolo /71,5-a_7 pyrimidine is 2ethoxycarbonylamino-6-methyl-5-oxo-4-n-propyl-4,520 dihydro-s-triazolo Z71,5 a J7 pyrimidine. 27 448 83 20. A composition as claimed in Claim 15 in which the amount of 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazolo Z~l,5-aJ7 pyrimidine is 0.1 to 5.0 parts per 100 parts of herbicidal bipyridylium quaternary 5 cation. 21. A composition aq claimed in Claim 15 in which the amount of ; 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-di• hydro-s-triazolo ^“l,5-a_7 pyrimidine is 0.25 to 2.0 parts per 100 parts of herbicidal bipyridylium quaternary 10 cation. 22. A composition as claimed in any of the preceding claims comprising a carrier or diluent. 23. A composition as claimed in Claim 22 in which the carrier or diluent is a solid. 24. A composition as claimed in Claim 22 in which the carrier or diluent is aqueous. 25. A composition as claimed in any of Claims 22 to 24 comprising a surface active agent. 26. A composition as claimed in any of Claims 22 to 25 2o comprising a stenching agent.
4. 4 8 8 3 27. A composition as claimed in Claim 2S in which the stenching agent is an alkyl pyridine base. 28. A composition as claimed in any of Claims 22 to 27 comprising a coloured dyestuff or pigment compound.
5. 29. A composition as claimed in Claim 24 comprising a gelling agent. 30. A composition as claimed in any of the preceding claims comprising any other herbicidal compound. 31. A herbicidal composition comprising an aqueous solution
6. 10 > of a salt of a pai«guat cation containing 50 to 400 grams per litre of the paraquat cation and from 0,1 to 5 parts by weight of 2-amino~6-methyl-5-oxo-4-npropyl-4,5-dihydro-s-triazolo Z~l»5-a_7 pyrimidine per 100 parts by weight paraquat cation.
7. 15 32. Compositions as claimed in Claim 1 substantially as herein described with particular reference to any one of the Examples.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15584/76A GB1507407A (en) | 1976-04-15 | 1976-04-15 | Herbicidal compositions |
| GB3458976 | 1976-08-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE44883L IE44883L (en) | 1977-10-15 |
| IE44883B1 true IE44883B1 (en) | 1982-05-05 |
Family
ID=26251408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE357/77A IE44883B1 (en) | 1976-04-15 | 1977-02-18 | Herbicidal compositions |
Country Status (39)
| Country | Link |
|---|---|
| JP (1) | JPS52128222A (en) |
| AR (1) | AR217825A1 (en) |
| BE (1) | BE852862A (en) |
| BG (1) | BG27712A3 (en) |
| BR (1) | BR7702375A (en) |
| CA (1) | CA1096191A (en) |
| CH (1) | CH628208A5 (en) |
| CU (1) | CU34684A (en) |
| CY (1) | CY1025A (en) |
| DD (1) | DD129965A5 (en) |
| DE (1) | DE2709307C2 (en) |
| DK (1) | DK145811C (en) |
| DO (1) | DOP1977002588A (en) |
| EG (1) | EG12605A (en) |
| ES (1) | ES457860A1 (en) |
| FI (1) | FI58711C (en) |
| FR (1) | FR2347883A1 (en) |
| GB (1) | GB1507407A (en) |
| GR (1) | GR61602B (en) |
| HK (1) | HK70179A (en) |
| HU (1) | HU179721B (en) |
| IE (1) | IE44883B1 (en) |
| IL (1) | IL51570A (en) |
| IT (1) | IT1077294B (en) |
| KE (1) | KE2994A (en) |
| LU (1) | LU77128A1 (en) |
| MY (1) | MY8000150A (en) |
| NL (1) | NL172115C (en) |
| NO (1) | NO146563C (en) |
| NZ (1) | NZ183410A (en) |
| OA (1) | OA05635A (en) |
| PH (1) | PH13711A (en) |
| PL (1) | PL101203B1 (en) |
| PT (1) | PT66431B (en) |
| RO (1) | RO71904A (en) |
| SE (1) | SE444631B (en) |
| TR (1) | TR19211A (en) |
| YU (1) | YU44402B (en) |
| ZM (1) | ZM2977A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE46306B1 (en) * | 1977-02-11 | 1983-05-04 | Ici Ltd | Safeguarded toxic chemical compositions containing an emetic |
| FR2588723B1 (en) * | 1985-11-12 | 1990-04-13 | Sds Biotech Kk | SOLID ANTI-SWALLOWING HERBICIDE COMPOSITION CONTAINING PARAQUAT AND A THICKENING AGENT |
| GB9015134D0 (en) * | 1990-07-10 | 1990-08-29 | Ici Plc | Herbicidal compositions |
| KR100329374B1 (en) * | 1999-09-22 | 2002-03-22 | 우종일 | Water dispersable granule comprising paraquat dichloride and its manufacturing method |
| CN108218766A (en) * | 2017-12-11 | 2018-06-29 | 东南大学 | A kind of preparation method of the compound containing paraquat or diquat |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH348003A (en) * | 1958-04-21 | 1960-07-31 | Complements Alimentaires S A R | Process for manufacturing toxic rat poison baits |
| IE33549B1 (en) * | 1968-09-13 | 1974-08-07 | Ici Ltd | S-triazolo (1,5-a) pyrimidine derivatives |
| AT292698B (en) * | 1969-09-12 | 1971-09-10 | Ici Ltd | Process for the preparation of new s-triazolo [1,5-a] pyrimidines |
| GB1406881A (en) * | 1972-04-13 | 1975-09-17 | Ici Ltd | Herbicidal compositions |
| GB1450531A (en) * | 1972-10-27 | 1976-09-22 | Ici Ltd | Herbicidal compositions |
-
1976
- 1976-04-15 GB GB15584/76A patent/GB1507407A/en not_active Expired
-
1977
- 1977-01-31 IT IT19802/77A patent/IT1077294B/en active
- 1977-02-16 CY CY1025A patent/CY1025A/en unknown
- 1977-02-18 IE IE357/77A patent/IE44883B1/en not_active IP Right Cessation
- 1977-02-22 NO NO770586A patent/NO146563C/en unknown
- 1977-02-22 NZ NZ183410A patent/NZ183410A/en unknown
- 1977-03-01 PH PH19512A patent/PH13711A/en unknown
- 1977-03-01 IL IL51570A patent/IL51570A/en unknown
- 1977-03-03 DE DE2709307A patent/DE2709307C2/en not_active Expired
- 1977-03-04 DK DK96777A patent/DK145811C/en not_active IP Right Cessation
- 1977-03-14 GR GR52988A patent/GR61602B/en unknown
- 1977-03-15 NL NLAANVRAGE7702758,A patent/NL172115C/en not_active IP Right Cessation
- 1977-03-17 RO RO7789689A patent/RO71904A/en unknown
- 1977-03-18 AR AR266919A patent/AR217825A1/en active
- 1977-03-19 EG EG163/77A patent/EG12605A/en active
- 1977-03-22 CU CU7734684A patent/CU34684A/en unknown
- 1977-03-23 PL PL1977196854A patent/PL101203B1/en unknown
- 1977-03-24 BE BE176106A patent/BE852862A/en not_active IP Right Cessation
- 1977-03-28 FR FR7709213A patent/FR2347883A1/en active Granted
- 1977-03-30 ZM ZM7729A patent/ZM2977A1/en unknown
- 1977-04-06 BG BG7735933A patent/BG27712A3/en unknown
- 1977-04-11 TR TR19211A patent/TR19211A/en unknown
- 1977-04-11 DO DO1977002588A patent/DOP1977002588A/en unknown
- 1977-04-13 JP JP4157577A patent/JPS52128222A/en active Granted
- 1977-04-13 LU LU77128A patent/LU77128A1/xx unknown
- 1977-04-13 SE SE7704238A patent/SE444631B/en not_active IP Right Cessation
- 1977-04-13 YU YU977/77A patent/YU44402B/en unknown
- 1977-04-13 DD DD7700198379A patent/DD129965A5/en unknown
- 1977-04-13 PT PT66431A patent/PT66431B/en unknown
- 1977-04-13 FI FI771161A patent/FI58711C/en not_active IP Right Cessation
- 1977-04-14 HU HU77IE775A patent/HU179721B/en unknown
- 1977-04-14 BR BR7702375A patent/BR7702375A/en unknown
- 1977-04-14 OA OA56141A patent/OA05635A/en unknown
- 1977-04-15 ES ES457860A patent/ES457860A1/en not_active Expired
- 1977-04-15 CH CH471677A patent/CH628208A5/en not_active IP Right Cessation
- 1977-04-15 CA CA276,251A patent/CA1096191A/en not_active Expired
-
1979
- 1979-09-27 KE KE2994A patent/KE2994A/en unknown
- 1979-10-04 HK HK701/79A patent/HK70179A/en unknown
-
1980
- 1980-12-31 MY MY1980150A patent/MY8000150A/en unknown
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| MK9A | Patent expired |