DK145811B - HERBICID AGENT - Google Patents

Description

(19) DENMARK

fj | (12) PUBLICATION WRITING (11) 145811 B

DIRECTORATE OF THE PATENT AND TRADEMARKET SYSTEM

(21) Application No. 967/77 (61 | lnta, A 01 N 25/32 (22) Filing date 4 Mar 1977 (24) Running day 4 Mar 1977 (41) Aim available 16 Oct 1977 ( 44) Submitted March 14, I983 (86) International Application No. - (86) International Filing Day - (85) Continuation Day - (62) Master Application No. -

(30) Priority 15-Apr. 1976, 15584/76, GB Aug 19 1976, 54589/76, GB

(71) Applicant IMPERIAL CHEMICAL INDUSTRIES LIMITED, London SW1P 4QG, GB.

(72) Inventor George Edward Davies, GB: David Mackie Foulkes, GB.

(74) Associate Company Chas. Hude.

(54) Herbicide agent.

The present invention relates to herbicidal agents containing an herbicide quaternary bipyridylium salt as active ingredient.

Over the years, many different pesticides have been developed for use in agriculture to control fungi, insects and weeds. These substances are necessarily toxic to certain types of life, but when used carefully and according to recognized regulations, they present no danger to human life. However, despite efforts to get those dealing with pesticides to practice hazardous practices in handling, pesticide abuse cases do occur.

OO A particularly uncertain practice in the case of liquid pesticides is to transfer a small amount of the concentrated pesticide T - *

ISLAND

No. 2 145811 to a household container, such as a beverage bottle, for later use at home. The risk associated with this practice is, of course, that a child or a careless adult who finds the bottle may drink the contents with consequent serious consequences.

It has now been found that it is possible to reduce the likelihood of serious consequences of such accidental swallowing by inducing vomiting. This may in some cases result in rapid removal of the pesticide from the stomach and digestive tract before lethal amounts of the pesticide can be assimilated by the body.

It is further discovered that admixture of a known triazole [1,5-a] pyrimidine derivative of the formula (I) listed below in a herbicidal quaternary bipyridylium salt in a herbicidal agent provides an agent which, if swallowed, is prone to induce vomiting and therefore expulsion of the agent.

The invention therefore relates to a herbicidal agent having a reduced health hazard containing a salt of a herbicide quaternary bipyridylium cation, and the agent is characterized in that it further contains an s-triazole [1,5-a] pyrimidine of the formula: - NHRX ( I) o ^ n ^ n /

T

R 2 is R 4 is hydrogen or a C 1-4 alkyl group or a COOC 2 H 2 group R 2 is a C 1-4 alkyl group or an allyl group and R 3 is an alkyl group wherein the salt of the herbicidal cation is a compound with the formula: (fjL_Γ ^ Ί) - [Χ] η ~ + # ~ \ / Γ ~ \ + 1 2 rn n- W n or U R-tf J- (f SR 5 [X] + \ h2CH ^ + \ = wherein R and R 4, which may be the same or different, are alkyl groups 3 145811 having 1 to 4 carbon atoms which may be substituted by hydroxyl, halogen, carboxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, carbamoyl or N-substituted carbamoyl , [X] n is an anion and n is an integer from 1 to 4 inclusive, which agent may optionally contain a diluent or carrier and optionally also a surfactant.

The S-triazole [1,5-a] pyrimidine ring structure is numbered as shown below: 7 1 6 in 1 N + 1 [J> 4 3

Special derivatives of 5-oxo-4,5-dihydro-s-triazole [1,5-a] pyrimidine for use in the composition of the invention are: 6-methyl-4-n-propyl-2-n-propylamino-2- amino-6-methyl-4-allyl-2-amino-4,6-di-n-propyl-2-ethoxycarbonylamino-6-methyl-4-n-propyl

A particularly useful triazole pyrimidine for use in the compositions of the invention is 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazol [1,5-a] pyrimidine (II ).

CH3 in V ih, <AKAi / (II) n-propyl 4 145811

Herbicidal quaternary bipyridylium salts for use in the agents of. the invention is those of the following formulas; 0-0 a.

Sr ^ n ^ § [x] + \ / + or I tx] n "wherein R and R ^, which may be the same or different, are alkyl groups having from 1 to 4 carbon atoms which may be substituted by hydro = xyl, halogen, carboxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, carbamoyl or N-substituted carbamoyl, [χ] η “is an anion and n is an integer from 1 to 4 inclusive.

Particularly preferred herbicidal quaternary bipyridylium salts are those listed below; 1,1-dimethyl-4,41-bipyridylium di (methylsulfate) (paraquat dimetho = sulfate) 1,1'-ethylene-2,21-bipyridylium dibromide (diquat dibromide) 1,1'-dimethyl-4,4'- bipyridylium dichloride (paraquat dichloride) 1,1'-di-2-hydroxyethyl-4,4'-bipyridylium dichloride 1- (2-hydroxyethyl-1'-methyl) -4,4 * -bipyridylium dichloride 1,1'-dicarbamoylmethyl 4,4'-bipyridylium dichloride 1,1'-bis-N, N-dimethylcarbamoylmethyl-4,4'-bipyridylium dichloride 1,1 * -dimethyl-4,4, -bipyridylium sulfate (paraquat sulfate) 1,1'-bis-N N-diethylcarbamoylmethyl-4,41-bipyridylium dichloride 1,1'-diacetonyl-4,4'-bipyridylium dichloride 1,1'-diethoxycarbonylmethyl-4,4'-bipyridylium dibromide

The names in parentheses of the compounds in the above list are the accepted common names for these compounds. "Paraquat" is thus the common name for the 1,1'-dimethyl-4,4'-bipyridylium cation. Paraquat is a particularly preferred Mpyridylium cation for trough in the compositions of the invention. A particularly preferred anion [X] n "is the chloride anion, for economic and convenience reasons, but any anion which provides a suitable water-soluble salt can be used if desired. The herbicidal effect is due solely to the cation, and for this reason the concentration of an agent with a herbicidal bipyridylium salt is often stated as the cation alone. The amount of a herbicide quaternary bipyridylium 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 solid, e.g. grains, or liquids, e.g. aqueous solutions.

In a preferred embodiment, a concentrated herbicidal agent containing an aqueous solution of a salt of a herbicide quaternary bipyridylin cation and a triazole pyrimidine as defined above is indicated. Preferably, the herbicidal kyat nutrient bipyridylium cation is paraquat.

The amount of herbicide quaternary Mpyridylium cation in the aqueous solution is preferably from 50 g to 400 g per ml. liter.

Preferably, the agent also contains a surfactant.

Surfactants may be cationic, nonionic or anionic. In general, cationic and nonionic surfactants are preferred over anionic surfactants for use in the compositions of the invention because the latter may react undesirably with the quaternary bipyridylium salt in the compositions. Examples of nonionic surfactants for use in the compositions of the invention include the condensation products of ethylene oxide with alkyl phenols such as octylphenol, nonylphenol and oxtylcresol.

Other nonionic agents are the partial esters derived from long chain fatty acids and hexanite anhydrides, e.g. sorbitan monolaurate, and the condensation products of these partial esters with ethylene oxide and the lecithins. Examples of cationic surfactants include quaternary salts and ethylene oxide condensates with amines, e.g. the

® (R

Substances marketed under the trademark Ethomeerr ', Ethoduomeen'-', 'Duoquad' and ArquacPk 145811 6 Particularly preferred surfactants are the combinations of surfactants described in British Patent no.

998,264 for use in preparations of herbicidal quaternary bipyridylium salts.

The preparation of triazole pyrimidines (I) is described in Danish Patent No. 137,498.

The emetic properties of the agent are determined primarily by the amount of triazole pyrimidine it contains. In determining the most appropriate amounts of triazole pyrimidine for use in a given agent, consideration must be given to the efficacy of the triazole pyrimidine in relation to the toxicity of the herbicide. The amount of triazole pyrimidine to be included is preferably such that any sample of the agent containing a potentially lethal dose of herbicide contains enough of the triazole pyrimidine to give an emetic effect. However, it is clear that neither lethal doses nor emetic doses can be measured directly in humans. You can only join them based on animal data.

Preferably, compositions of the invention contain from 0.1 to 5 parts by weight of the triazole pyrimidine (e.g., triazole pyrimidine II) per day. 100 parts of the herbicidal quaternary bipyridylium cation (e.g., paraquat). Conveniently, the amount of the triazole pyrimidine (e.g., triazole pyrid = midine II) is 0.25 to 2.0 parts per day. 100 parts of herbicide quaternary bi = pyridylium cation (eg paraquat).

Concentrated aqueous compositions of the invention are corrosive.

They must be handled with care to avoid spraying on the eyes or skin and should not be allowed to come into contact with corrosible metals before dilution.

The agents of the invention may also contain colored substances or pigments to give them a characteristic or distinct color. Examples of such compounds are "Monastral Blue BNV Paste" and "Lissamine Turquoise VN 150".

The compositions of the invention may also contain a stinking agent. Examples of such stinkers are: Alkyl pyridines, as described in British Patent No. 1,406,881, n-valerianic acid and tetrahydrothiophene.

7 145811

If desired, the triazole pyrimidines (I) can be incorporated into thixo = tropic preparations of herbicidal quaternary salts. In particular, the triazole = pyrimidines (I) can be incorporated into the compositions of herbicidal quaternary bipyridylium salts disclosed in Danish Patent No. 138,822. These compositions comprise an aqueous solution of a herbicide quaternary bipyridylium salt containing a gelling agent, e.g. finely divided silica, or a combination of the xanthan gum marketed under the trademark Kelzan® with sodium metaborate. Xan = than rubber is a complex polysaccharide.

The agents of the invention may also contain another herbicide in addition to a herbicide quaternary bipyridylium salt as defined above. Examples of such herbicides are:

Amides (e.g., N, N-diallyl chloroacetamide, 3,3-dichloropropionanilide, N- (3-chloro-4-methyl-phenyl) -2-methylpentamide).

Carbamates (e.g., isopropyl-N-phenylcarbamate, isopropyl-N- (3-chloro = phenyl) carbamate, 4-chloro-2-but-2-ynyl-N- (3-chlorophenyl) carbamate, 2-> chlorallyl) -N, N-diethyldithiocarbamate).

Urea / Anilides (e.g., N, N'-di- (2,2,2-trichloro-1-hydroxy = ethyl) urea, 3,4-dichloroacetanilide, O-chloroisobutyranilide, α-bromo-3,4- dichloroacetanilide, 3,4-dichloroformanilide, 2-acetamido-3-chlorotoluol).

Diazines (e.g., 3,4,5,6-tetrahydro-3,5-dimethyl-2-thio-2H-1,3,5-thiadiazine, 5-bromo-3-isopropyl-6-methyluracil, 5- amino-4-chloro-2-phenyl-3-pyridazone, 1,2,3,6-tetrahydro-3,6-dioxopyridazine),

Triazines (e.g., 2-chloro-4,6-bisethylamino-1,3,5-triazine, 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine, 2-chloro-4, 6-Bisisopro = pylamino-1,3,5-triazine, 4-ethylamino-6-isopropylamino-2-methoxy-1,3,5-triazine, 4,6-bisisopropylamino-2-methoxy-1,3,5 triazine).

Addition of the triazole pyrimidines (I) to the agents of the invention has no known deleterious effect on the herbicidal activity of the agents. The invention is illustrated by the following examples.

145811 8

Example 1

This example illustrates an agent of the invention comprising 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine (II) in aqueous solution.

Ingredients% w / v

Paraquat concentrate x (II) 0.05

Water to 100 ml (where x gives 200 in 5 g / liter paraquat cation)

The paraquat concentrate is a solution of paraquat dichloride containing 25 ° to 30% by weight of 1,1'-dimethyl-4,4'-Mpyridylium cation. The amount used was chosen to give an agent containing 20% w / v paraquat cation. The agent is produced by simply stirring the horse ingredients together.

Example 2

This example illustrates an agent of the invention which comprises the triazole pyrimidine (II) in aqueous solution. The agent comprises the following components.

Ingredients% w / v

Paraquat concentrate x

Sodium Metabolate 1.3

Sodium benzoate 2.0

Lissapol NX 1.1 DS 4392 4.1

Silcolapse 5000 0.06 (II) 0.05

Water to 100 ml (where x gives 200 - 5 g / liter paraquat cation) "Lissapol" NX is a trademark of a surfactant comprising a condensate of from 7 to 8 molar amounts of ethylene oxide with 1 molar amount of p-nonylphenol.

DS 4392 is a code number for a surfactant comprising a mixture of amines derived from soybean fatty acid condensed with approx.

9 molar amounts of ethylene oxide.

Silcolapse® is a trademark of an anti-foaming agent comprising a silicone derivative.

The above-described agent was prepared by simply stirring the ingredients together.

Example 3

This example illustrates an agent of the invention which comprises a gelling agent in addition to the triazole pyrimidine (II). The agent comprises the following components.

Ingredients Amounts in grams

Paraquat concentrate x

Kelzan * (xanthan gum). 0.4 (added as 1% solution in water)

Sodium etaborate 0.014

Lissapol NX 1.1 DS 4392 4.1 (II) 0.05

Silcolapse® 5000 0.01

Water to 100 ml (where x gives 200 - 5 g / liter paraquat ion)

The above-described agent was prepared by simply stirring the ingredients together and was sufficiently liquid after preparation to be poured into containers. After standing for 15 to 20 minutes, the agent formed a gel which could not be poured unless strongly shaken.

Example 4

This example illustrates a dry free-flowing granular agent which is both stable upon storage and can easily be converted into an aqueous solution for use as a spray liquid.

A solution of the following composition was prepared in which the percentages are by weight.

10 U5811

Paraquat dichloride 33 »0 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine (II) 0.1

Sodium Metabolate 2.5

Potassium pho 1.6

Lissapol NX 24.0

Water 38.8 100 310 g of the above solution was added in a thin stream to 690 g of dried magnesium sulfate contained in the bowl of a HOBART C.E. 100 dough mixers ("HOBART" is a trademark). The resulting product, which was dry, was then passed through a granulator and finally stirred in a sieve with 30 meshes per minute. linear inch to remove dust.

The resulting grains were at least 0.9 mm in size and had a dissolution time of 150 seconds.

Example 5

This example illustrates an agent of the invention comprising 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine (II) and an aqueous solution baking agent.

Ingredients% w / v

Paraquat concentrate x n -value free acid 1.0 II 0.05 DS 4392 4.0

Silcolapse 0.01

Lissapol NX 1.0

Water to 100 ml (where x gives 200 g / l paraquat ion).

The above-described agent was prepared by simply stirring the ingredients together.

Example 6

This example illustrates an agent of the invention which comprises 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine ( II) in a thickened, colored, 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 ml (where x gives 200 g / l paraquat ion).

"Synperonic" and "Nansa" are trademarks. Synperonic 2 is a condensation product of one mixture of 67% C C and 33% C-j aliphatic alcohols with two equivalents of ethylene oxide. Synperonic 16 is a condensation product of a mixture of 67% C- and 33% C15 al aliphatic alcohols with sixteen equivalents of ethylene oxide. Nansa 1106 is sodium dodecyl benzene sulfonate (generally C1 straight chain). Monastral BNVS paste is a dispersion containing 15% w / v copper phthalocya = nin pigment in water. Pyridine base is a mixture consisting essentially of alkyl pyridines.

Example 7

This example illustrates an agent of the invention which comprises 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine (II) in aqueous solution.

Ingredients% w / v diquat dibromide x

Sodium molybdate 0.18

Potassium phosphate (as a mixture of potassium hydrogen phosphate and potassium dihydrogen phosphate) 2.75 (II) 0.05 water to 100 ml (where x gives 140 - 5 g / l diquat ion).

12 145811

The diquation is the 1,1'-ethylene-2,2'-pyridylium cation. The above-described agent was prepared by simply stirring the ingredients together and had a pH of 6.5 - 0.5.

Example 8

This example illustrates an agent of the invention comprising 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine (II) in aqueous solution.

Ingredients% w / v

Morfamquat dichloride x II 0.05 water to 100 ml (where X gives 300 - 5 g / l morphamquat ion).

The morph equation is the 1,1'-bis (3,5-dimethylmorpholinocarbonylmethyl) -4,4, -bipyridylium ion. The above-described agent was prepared by simply stirring the ingredients together.

Example 9

This example illustrates an agent of the invention comprising 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine (II) in aqueous solution.

Ingredients% w / v 1,1'-bis (diethylcarbamoylmethyl) 4,4, bipyridylium dichloride x

Tween 20 (II) 0.05 water to 100 ml (where x gives 200 - 5 g / l, 1,1'-bis (diethylcarbamoylmethyl) -4,4'-bipyridylium ion).

The above-described agent was prepared by simply stirring the ingredients together.

"Tween" is a trademark. Tween 20 is a condensation product of one mole of sorbitan monolaurate with twenty moles of ethylene oxide.

145811

Example 10 13

This example illustrates an agent of the invention which comprises 2-n-propylamino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole- [1,5-a] pyrimidine in aqueous resolution.

Ingredients% w / v

Paraquat concentrate x 2-n-propylamino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine 0.05 water to 100 ml (where x gives 200 - 5 g / liter paraquat cation)

Example 11

This example illustrates an agent of the invention which comprises 2-amino-5-oxo-4,6-di-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine in aqueous solution.

Ingredients% w / v

Paraquat concentrate x 2-Amino-5-oxo-4,4-di-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine 0.05 water to 100 ml (where x gives 200 - 5 g / liter paraquat cation)

Example 12

This example illustrates an agent of the invention which comprises 2-ethoxycarbonylamino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine in aqueous solution.

Ingredients% w / v

Paraquat concentrate x 2-Ethoxycarbonylamino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine 0.05 water to 100 ml (where x gives 200 in 5 g / liter paraquat cation)

Example 15 14 1Λ5 811

This example illustrates an agent of the invention which comprises 2-aminoO-6-methyl-5-oxo-4-allyl-4,5-dihydro-α-triazole [1,5-a] pyrimidine in aqueous solution.

Ingredients% w / v

Paraquat concentrate x 2-amino-6r methyl-5-oxo-4-allyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine 0.05 water to 100 ml (where x gives 200-5 g / liter paraquat cation)

Example 14

This example illustrates the reduced likelihood of serious consequences of ingestion of a herbicidal agent of the invention. Hancynomulgus monkeys (Macaca fasicularis) with a body weight in the range of 3.5 - 5 kg were used.

Sample 1

Eight monkeys were dosed with a herbicide with a quaternary bipyridyldium salt as set forth below containing 100 mg paraquation / kg body weight.

The required amount of an agent comprising;

Ingredients% w / v

Paraquat x

Lissapol NX 1.1 DS 4392 4.1

Silcolapse 5000 0.01

Water to 100 ml (where x gives 200 - 5 g / liter paraquation) was diluted with water to 20 ml to give 100 mg paraquation / kg body weight, to which was added 10 g Complan (trademark of a 15 U5811 carboxymethyl cellulose). . All eight monkeys died.

Sample 2

Eight monkeys were dosed with an agent according to the invention comprising the same amount of the same agent (giving 100 mg paraquation / kg body weight) as in sample 1 plus 2-amino-6-methyl-5-oxo-4-n-propyl-4,5 -dihydro-s-triazole [1,5-a] pyrimidine (2 mg / kg body weight).

Only two of the monkeys died. The six surviving animals all vomited in the first hour after dosing.

Sample 3

Sample 1 was repeated with four monkeys. All the monkeys died within 3-4 days.

Sample 4

Sample 2 was repeated with four monkeys and performed simultaneously with Sample 3.

All the monkeys threw up, two approx. 20 minutes after dosing, one after approx. 45 minutes, and one after approx. 8 hours. The three monkeys who threw up early survived. The monkey, who threw up later, died.

Experiment with dogs.

He used Beagler with a body weight in the range of 9-12 kg. Sample 5

Four dogs were dosed with a herbicide with a quaternary bipyridyldium salt as set forth below in an amount of 20 mg paraquation / kg body weight.

Ingredients% w / v

Paraquat Concentrate x

Water to 50 ml 16 145811

To this solution was added 6 g of carboxymethyl cellulose (x gives 20 mg paraquation / kg body weight).

Three of four dogs died during the first week after dosing.

Sample 6

Four dogs were dosed with an agent of the invention comprising the same amount of the same composition (giving 20 mg paraquation / kg body weight) as in Sample 5 plus 2-amino-6-methyl-5-oxo-4-n-propyl-4,5 -di = hydro-s-triazole [1,5-a] pyrimidine (3 mg / kg body weight).

All the dogs vomited within an hour of dosing and none died.

Sample 7

Sample 5 was repeated but with the agent comprising 30 mg paraquation / kg body weight. Three out of four dogs died.

Sample 8

Sample 6 was repeated but with the agent comprising 30 mg paraquation / kg body weight. All the dogs vomited within an hour of dosing and within them died.

Sample 9

Sample 6 was repeated but with the agent comprising 2 mg of 2-amino-6-methyl-5-oxo-4-n-propyl-4,5-dihydro-s-triazole [1,5-a] pyrimidine / kg body weight. All four dogs vomited within 15 minutes and survived.

Example 15

This example illustrates the emetic strength of several representatives of the s-triazole [1,5-a] pyrimidine class of formula I.

The pyrimidine derivatives were administered orally to Beagle dogs (body weight about 10 kg) either by gastric incubation (with the material in 50 ml of a 12.5% w / v carboxyurea hyicilulose suspension) or when the material was particularly insoluble in water or by a gel-tin capsule; the table shows the time within which emesis occurred.

Derivative of 5-oxo-4,5-dihydro-s-Dose Time (min) within triazole [1,5-a] pyrimidine mg / dog which occurred emesis 6-methyl-4-n-propyl-2-n-propylamino 30-60 2-amino-4,6-di-n-propyl 30-60 2-amino-6-methyl-4-allyl 25 30-60 250 30-60

From the table, it will be seen that vomiting occurred within 30-60 minutes of administration of the pyrimidine derivative. Since the toxic effects of bipyridylium herbicides manifest only within a period of days (see Sample 3 above), while the emetic effect of the pyrimidine derivatives is seen within a period of hours, it is clear that an agent containing a bipyridylium herbicide and a triazole pyrimidine derivative of formula I is likely to be excreted by vomiting before it can cause any serious toxic effects.

Example 16

This example illustrates the reduced likelihood of serious consequences of ingestion of a herbicidal agent containing the bipyridylium herbicide called diquat dichloride and having the formula 2 = 1- W +

Two monkeys with a body weight of 3.25 and 3.40 kg received a dose of diquat equivalent to 400 mg diquat per kg body weight. The dose was given in 50 ml of tap water. The first monkey died within two days and the second died 8-24 hours after dosing.

Two other monkeys with a body weight of 2.75 and 2.45 kg received doses of diquat

Claims (1)

An herbicidal agent with a reduced health hazard containing a salt of a herbicide quaternary bipyridylium cation, characterized in that it further contains an s-triazole [1,5-a] pyrimidine of the formula: R a! in? where is hydrogen or a C1-6 alkyl group, or a COOC2H5 group, 2 ± ^ A3 R is a C1-6 alkyl group or an allyl group and R1- is a C1-6 alkyl group wherein the salt of the herbicidal cation is a compound of the formula: x I_N I § cxin- \ / + ch2ch2 + or iø— <Q> -r1 in [χιή_