CS232746B2 - Herbicidal agent with a cultural plant preservative - Google Patents

Abstract

The composition contains a pyrrolidone compound as a herbicidally active component and a protective component where R3 represents an ethyl group or an allyl group, Rα represents a benzyl group or an allyl group, or R3 and Rα together with the nitrogen atom to which they are bound form a 2,2,5-trimethyl-1,3-oxazolidine group, in a weight ratio of antidote to pyrrolidone compound of 0.001:1 to 30:1.

Description

The invention relates to antidotes for pyrrolidene herbicides; in particular it relates to the following four antidotes: N-ethyl-N-benzyldichloroacetamide, N,N-diallyldichloroacetamide and 2,2,5-trimethyl-3-(dichloroacetyl)oxazidine.

Herbicidally active substance means a compound which .restricts or modifies plant growth; ,that is to say, it destroys the plant, slows its growth, causes leaf loss, desiccation of the plant, reduces the rate of growth, prevents growth, stimulates growth or otherwise influences growth. The term "plant" here always means all physical parts of the plant, including seeds, seedlings, seedlings, roots, tubers, stems, culms, leaves and fruits. "Plant growth" here always means all stages of the plant from development from the germinating seed to the natural or induced end of the plant's life.

Herbicides are generally used to control or destroy weedy plants. Herbicides are commercially very successful because it has been found that such weed growth control increases crop yields and reduces harvest costs.

The most common methods of using herbicidal compositions include incorporating the herbicidal composition into the soil before sowing the crop plants, incorporating it into the seed furrow and covering it with soil, treating the seeded soil on the surface before seed emergence, and treating the plants and soil after seed emergence.

Herbicide manufacturers generally recommend a range of application rates and concentrations of herbicide to achieve maximum weed control. These recommended rates vary from 0.0112 to 56 kg/ha and are generally 0.112 to 28 kg/ha. The term "herbicidally effective amount" here always refers to the amount of herbicidally active substance that limits or modifies plant growth. The actual amount of herbicide used depends on various conditions, including the sensitivity of the weed plant in question and the overall costs.

The most important factor affecting the usefulness of a given herbicide is its selectivity with respect to the crop. In some cases, the crop is sensitive to the action of the herbicide. In addition, certain herbicidally active compounds are phytotoxic with respect to certain weed plants, but not to other weed plants. In order for a herbicide to be effective, it must cause minimal damage to the crop plants, preferably no damage at all, while causing maximum damage to the weed species in the crop.

Depending on the herbicide used, pyrrolidone herbicidally active substances have one of two different effects on crop plants and weeds. If the pyrrolidone compound is prepared and used in the form of an emulsifiable concentrate, it causes bleaching of the crop plant in the early stages of its growth. Bleaching is caused by the loss of pigmentation in the plant and is manifested by yellowing of the leaves of the plant.

If the pyrrolidone compound is formulated as a microcapsule, the bleaching of the plant is significantly reduced. However, the effectiveness against weed plants is reduced.

In order to maintain the beneficial hefltioidiirlro action, that is to achieve maximum adverse .action on weed plants and to reduce to a minimum the adverse effect on crop plants, numerous antidotes have been prepared for herbicidally active substances. These antidotes reduce or eliminate the harmful effect on crop plants while maintaining or increasing the destructive effect of the herbicidal composition on weed plants; see for example U.S. Patent Nos. 3,959,304, 4,021,324 and 4,021,229 and Belgian Patent ;846,894.

The exact mechanism by which an antidote reduces the adverse effects of a herbicidally active agent on a crop plant has not yet been elucidated. An antidote compound may be a drug, an interfering compound, a safener compound or an antagonistic compound. As used herein, the term "antidote" refers to a compound that acts to produce herbicidal selectivity, i.e., it retains herbicidal phytotoxicity with respect to weedy plants and reduces or eliminates cytotoxicity with respect to crop plants. The term "antidote-effective amount" refers to the ability of an antidote compound to counteract the cytotoxic response of a crop plant to a herbicide.

Compounds of the general formula II have been found to be effective antidotes for pyrriftUdoníwáš herbicidally active substances for various crop plants

About R3

II /

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R3 is an ethyl group or an allyl group,

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JR3 m 1R4 form, together with the nitrogen atom to which they are bound, a 2 _ί 2£τΐτηη&ΰίΐγιΜ,Λ -oxazolidine group,

The essence of the invention is a two-component herbicidal composition which contains

a) a herbicidally effective amount of a pyrrolidone compound of formula I

X o

I am

Y-C-C\ N ./

(AND)

Z-CH-C~CH _Z

where means

X is a hydrogen atom, chlorine or methyl group,

Y is a hydrogen atom, a chlorine atom or a bromine atom,

From a chlorine atom or a bromine atom and

R is a hydrogen atom, an alkyl group with 1 to 4 carbon atoms inclusive, an acetyl group, a chlorine, bromine, fluorine or iodine atom, a trifluoromethyl group, a nitro group, a cyano group, an alkoxy group with 1 to 4 carbon atoms inclusive, an alkylthio group with 1 to 4 carbon atoms inclusive, an alkylsulfinyl group with 1 to 4 carbon atoms inclusive, an alkylsulfonyl group with 1 to 4 carbon atoms inclusive, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a pentafluoropropionamido group or a 3-methylureido group,

R1 is a hydrogen atom, an alkyl group with 1 to 4 carbon atoms inclusive, a chlorine atom or a trifluoromethyl group and

R2 is an alkyl group of 1 to 4 carbon atoms inclusive, or a hydrogen atom and

b) a non-phytotoxically effective amount as an antidote of a compound of general formula II

About Rs.

II /

CI2CHC-—N

Rd where means

R3 is an ethyl group or an allyl group,

R4 is a benzyl group or an allyl group, or

R3 and Rd together with the nitrogen atom to which they are attached form a 2,2,5-trimethyl-1,3-oxazolidine group, in a ratio of component b) to component a) by weight of 0.001:1 to 30:1.

Examples of compounds of general formula II useful as ^{an antidote include compounds of formula CH C} - _CH

Cl o

H—C—C—N

Cl

CH2-CH = CH2

CH2—CH = CH2

Cl O CH2—CH—CH3

I II /

H—C—C—N

I \

Cl c - o / \

CH3 CH3

In a preferred case, X represents a hydrogen atom, Y represents a chlorine atom, Z represents a chlorine atom, R represents an m-trifluoromethyl group, R1 represents a hydrogen atom and _R2 represents a hydrogen atom.

The composition according to the invention is suitable for controlling unwanted vegetation while simultaneously reducing the herbicidal effect of the pyrrolidone active ingredient on cultivated plants.

Herbicidal selectivity is required in a herbicidal composition when used to treat soil, seeds, seedlings and plants.

Pyrrolidone compounds of formula I can be prepared by the method described in U.S. Patent No. 4,110,105.

The N-Ethyl-N-benzyldichloroacetamide compound, used as an antidote, can be prepared as follows: 14.2 g (0.105 mol) of N ethylamine, 4.0 g (0.1 mol) of sodium hydroxide, 50 ml of water and 100 ml of methylene chloride are placed in a reaction flask. 14.7 g of 2,2-dichloroacetyl chloride are added dropwise with cooling with dry ice over a period of three minutes. Cooling is stopped and the mixture is stirred for a further 18 minutes.

The reaction mixture was separated and the organic phase was washed twice with dilute hydrochloric acid, twice with 5% sodium carbonate solution, dried over magnesium sulfate and stripped under water pump vacuum to give 21.9 g of 2,2-dichloro-N-ethyl-N-benzylacetamide (residual liquid). n _D ³⁰ = = 1.5449. The structure of the compound was confirmed by infrared spectroscopy.

The N,N-Diallyldichloroacetamide used in the invention can be prepared in the following manner:

Dissolve 3.7 g (0.025 mol) of dichloroacetyl chloride in 100 ml of dichloromethane and cool to 5 °C in an ice bath. Add 4.9 g (0.05 mol) of diallylamine slowly, maintaining the temperature at approximately 10 °C.

The reaction mixture is stirred at room temperature for four hours, washed twice with water, dried over magnesium sulfate, filtered and stripped. The yield is 4.0 g of diallyldichloroacetamide. n _D ³⁰ = = 1.4990. The structure of the compound is confirmed by nuclear magnetic resonance spectroscopy.

2,2,5-Trimethyl-3-(dichloroacetyl)oxazolidine, used in the present invention, can be prepared by the method described in U.S. Patent No. 3,959,304.

For testing the herbicidal composition according to the invention, a stock solution of pyTable I

Type of active substance

Stock solution Composition active substance water mg* ml of rrolidone active substance by diluting the desired amount of herbicidally active substance with water, or in a mixture of acetone and water. Examples of solution composition and doses used are given in Table I.

Herbicidal active substances used dose acetone ml/bowl** kg/ha ml

1-m-trifluoromethylphenyl-3- 781 100 — 2.67 1.4 chloro-4-chloromethyl-2-pyrrolidone 122 20 20 2.73 0.56 * weight is measured as mg of the 2E product, i.e. 0.24 kg of active ingredient in 1 liter of the herbicide product ** the dimensions of the bowl are 151 x 241 mm, approximately 4 mg/bowl corresponds to 1.12 kg/ha.

In all cases, the herbicide is applied to the soil surface after sowing the seeds and before the plant emerges, i.e., pre-emergence herbicide use. The herbicide is sprayed onto the soil either as a tank mix with an antidote, or on its own after pre-emergence soil treatment, or used before sowing, or the antidote is applied into the furrow.

Table II

Stock solutions of the above-defined antidotes are prepared in the desired concentrations by diluting the required amount with acetone or a mixture of acetone and water. Examples of solution compositions, doses and methods of use are given in the following Table II.

Antidote stock solutions

Composition Antidote* mg Acetone ml Water ml Use ml/bowl kg/ha How to use 95 15 — 0.30 1.12 IF** 95 15 — 1.50 5.60 IF 60 20 20 2.67 1.12 PUS*** 300 20 20 2.67 5.60 DOG

* technical quality antidote ** in-furrow application of antidote *** application of antidote to the soil surface before emergence

Antidote solutions are used either by incorporation into the furrow, application before sowing, or application to the soil surface before emergence using a sprayer or spray plate.

For furrow application, a 473 ^cm3 soil sample containing the previously applied herbicide is taken. After leveling the soil and creating a furrow, the seeds of cultivated plants and weeds are sown to a depth of 1.27 cm. The bowl is divided into two parts by a wooden partition. The stock solution of the antidote is sprayed directly onto the seeds and onto the furrow soil. The seeds are then covered with previously removed soil. The non-antidote treated part of the bowl is then compared with the treated part and the movement of the antidote sideways through the soil is assessed.

In other tests, the antacids are applied to the soil before the seeds are sown. Such a treatment is referred to as a pre-sowing treatment. Stock solutions of the antacids are injected into the soil from tanks in which the proportions of the components are mixed to achieve the desired doses. The antacid-treated soil is placed in a pan, leveled, and furrowed 1.27 mm deep. Sufficient seeds are sown to obtain a sufficient number of values for each treatment. The seeds are then covered with the antacid-treated soil.

Control dishes containing crop plants treated with herbicide alone, along with other dishes also treated with antidote, are placed in a greenhouse maintained at 21.1 to 32.2° C. The dishes are moistened by spraying as needed to ensure good plant growth.

All tests always use silty-sandy soils treated with 50 ppm of the commercially available fungicide N-[(trichloromethyl)thio]-4-cyclohexene-1,2-dicarboximide and 18-18-18 fertilizer, which always contains 18% by weight of nitrogen, phosphorus pentoxide and potassium oxide.

Plant damage is assessed 4 weeks after application of the antivenom. The efficacy of the antivenom is determined by visually comparing the damage to crop plants occurring in the test dishes compared to untreated dishes.

The crops used in the test are millet, wheat, cotton, rice, barley, chickpeas and soybeans. The effect of the tested chemicals on the weeds Echinochloa crusgalli, Setaria viridis, Avena fatua and Brassica spp. are also assessed.

Explanatory notes to tables III, IV, V, VI, VII, VIII and IX.

Herbicidal active substances 1-m-trifluoromethylphenyl-3-chloro-4-chloromethyl-2-pyrrolidone

N-m-cyanophenyl-3-chloro-4-chloromethylpyrrolidone-2

Ways of use

IF introduction of antidote into the furrow (the soil is then treated only with the herbicidally active substance]

PPI application of antidote before sowing PES application of herbicidally active substance or antidote to the soil surface before emergence TM tank-mixed solution of herbicidally active substance and antidote.

If no antidote is used, the corresponding column shows "O". The values in such a row show the percentage damage to cultivated plants when treated with the herbicide alone, used at the indicated dose.

The doses of both the herbicidally active substance and the antidote are given in kg/ha.

Damage to crop plants (Tables II, V and VII) or weed plants (Tables IV, VI and VIII) is reported as the percentage damage to the plant compared to the untreated plant score. Damage is given by the number of plants damaged and the degree of damage to each plant. This score is made 4 weeks after treatment with the herbicide alone or with the herbicide in combination with an antidote.

A cross (+) in Tables II, V and VII indicates that the antidote is effective in reducing herbicidal damage to the crop plant.

Tables IV, VI and VIII demonstrate that the tested antidotes have no effect on weed plants, i.e. the action of the herbicidally active substance remains preserved even in the presence of the antidote.

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Table IV

Herbicidal efficacy

Antidote: N-Ethyl-N-benzyldichloroacetamide

Herbicidal Antidote active ingredient dose dose method of composition use hedgehog -Bér chicken's foot green

1-m-trifluoromethylphenyl-3-chloro-4-chloromethyl-2-pyrrolidone

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Table VI Antidote: Ν,Ν-Diallyldichloroacetamide

Herbicidal Antidote Hedgehog Bér Oat Mustard Cane Nettle Abutilon active ingredient dose dose method cocksfoot deaf wild annual composition use percentage damage o o o o o o o o o rH rH ,rH rd rS

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Table VII

Antidote efficacy of 2,2,5-trimethyl-3-(dichloroacetyl) oxazolidone

Herbicidal Antidote Millet Wheat Cotton Rice Barley Corn Soybean active ingredient dose dose method percentage damage composition use oioo

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Field trials with 2,2,5-trimethyl-3-(dichloroacetyl)ioxazolidine.

2,2,5-trimethyl-2-(dichloroacetylioxazolidin) is tested in the field. Plots measuring 1.8 m X 9.1 m are prepared for sowing. Seeds are sown in the plot with a seeder to a depth of 19 to 38.1 mm, depending on the plant species. The plots are then treated with the herbicide alone or with a composition containing the herbicidally active substance and an antidote.

The treatment of the land is carried out by a device that releases 345 l/ha of the treatment agent. The required amount of 0.349 l is applied to the land. The treatment agent used, containing a herbicidally active substance and an antidote, contains 0.24 kg of active ingredient per liter of the agent.

The required amount of herbicidal active substance or antidote for one plot can be calculated as follows:

Required amount of agent = A X B X XC X D X E

A amount of active ingredient in kg/ha B amount of product in l per kg of active ingredient C 1 ml/l D 1 acre

E plot area in m ²

For the use of only the herbicidally active substance at a rate of 0.373 kg/ha, the following calculation is used:

Amount of product =

0.372 kg/ha (4.177 1/kg)

X 3785.3 ml X 1 acre

X 16.72 m ² = 2604 ml/plot

The amount of the product is measured and diluted to 399.1 ml with water. The herbicide is then applied at a rate of 344.9 l/ha.

When using a herbicide and an antidote simultaneously, the herbicide and the antidote are measured separately and then mixed together. This solution is then diluted to the required 0.389 liters with water. Each plot is sprayed once.

Explanatory notes to Tables XI, XII, XIII and XIV Herbicidally active substance = — 1-m-trifluoromethylphenyl-3-chloro-4-chloromethyl-2-pyrrolidone

Antidote = = 2,2,5-trimethyl-N-dichloroacetyloxazolidine

The doses of the herbicidally active substance and antidote are always given in the tables in kg/ha.

Damage to crop plants (phytotoxicity) is measured quantitatively as a measure of the degree of bleaching. This assessment is carried out 4 to 5 weeks after germination.

The bleaching rate refers to the number of plants showing symptoms of plant yellowing, or the degree of bleaching. Two yellowed plants out of 10 are considered 20% bleaching.

The degree of bleaching is a measure of the severity of plant damage. It expresses the area of bleached leaves in relation to the total leaf area of the entire plant and is expressed as a percentage.

Percent weed control is a comparison of weed damage in treated plots compared to weed damage in untreated, control plots. Weed damage is a function of the number of plants damaged by each plant. Weed damage and phytotoxicity are assessed simultaneously.

Table XI shows the effect on corn of the antidote together with the herbicidally active substance, formulated as an emulsifiable concentrate. 15 types of corn are tested. For simplicity, the individual types of corn are designated by the following letters:

A = Cargill 924

B = Cargill 967

C = Dekalb XL—25 A

D = Dekalb XL—55A

E = Dekalb XL—72B

F = Dekalb XL—729 (F2)

G = PAG SX—17A

H = PAG SX—189

I = PAG SX—249

J = Northrup King PX—79

K = Northrup King PX—95

L = Northrup King PX—707

M = Pioneer 3541

N = Pioneer 3183

O = Trojan T—1189

Table XII shows the results of the effect on weed plants of the antidote together with the herbicidally active substance, which are processed into an emulsifiable concentrate. For simplicity, the individual weed plants in the table are designated by the following letters:

AA = Echinochloa crusgalli

BB = honeycreeper (Eragrostis diffusa)

CC = Common purslane (Eriochloa graclis) DD = Common purslane (Portulaca oleracea) EE = Field bindweed (Convolvulus arvensis) FF = Amaranthus spp.

GG = merlin (Chemopodium spp.j

HH = weed plant Tribulus terrestris

Table XIII shows the effect of the antidote together with the herbicidally active substance, which are processed into microcapsules, on cultivated plants. Barley, oats and wheat are tested as cultivated plants.

Table XIV shows the effect on weed plants of the antidote together with the herbicidally active substance, which are processed into microcapsules. The four weed plants are designated by the following letters:

II = millet Panicum fasciculation JJ = millet Panicum miliaceum KK = wild oats Avena fatua LL = green grass Setaria viridis

The remaining 8 weed plants according to Table XIV were not sown. They are the plants marked in the table with the following letters:

MM = purslane (Portulaca oleracea)

NN = Amaranthus spp.

OO = weed plant Calandrinia ciliata PP = merlin (Chemopodium spp.)

QQ = Shepherd's purse {Capsella bursa-pastoris)

RR = meadow grass (Poa spp.)

SS = Common hedgehog (Echinochloa crusgalli)

TT = hedgehog Echinochloa colonum

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Effect on weed plants of 2,2,5-trimethyl-N-dichloroacetyloxazolidine in a mixture with 1-m-trifluoromethylphenyl-3-chloro-4-chloromethyl-2-pyrrolidone, processed into an emulsifiable concentrate

Herbicidal active ingredient dose Antidote dose AA BB CC DD EE FF GG HH 0.37 — 76 + 92 92 97 30 98 98 86 0.37 0.56 85 90 91 99 10 99 99 84 0.56 — 85 95 95 99 25 98 98 95 0.56 0.56 85 93 97 99 11 99 99 93

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Table XI

Effect on cultivated plants of 2,2,5-trimethyl-N-dichloroacetyloxazolidine in a mixture with 1-m-trifluoromethylphenyl-3-chloro-4-chloromethyl-2-pyrrolidone, processed into microcapsules

Herbicidal active ingredient dose Antidote dose Barley Oats percentage damage Wheat 0.224 — 1+ 1 1 0.224 0.56 5 3 1 0.224 1.12 5 4 3 0.280 3 3 1 0.280 0.56 5 5 1 0.280 1.12 5 5 3 0.370 — 4 4 3 0.370 0.56 5 5 1 0.370 1.12 8 5 3 values are the mean of two replicates

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The tests performed show that the compositions containing pyrrolidone herbicidally active substances and the tested antidotes are effective for controlling weeds and for reducing the herbicidal and harmful effect on a wide range of cultivated plants. The antidotes used do not reduce the herbicidal effect on weed plants.

2,2,5-Trimethyl-N-dichloroacetyloxazolidine shows good protective action when 1-m-trifluoromethylphenyl-3-chloro-4-chloromethyl-2-pyrrolidone is used as the herbicidal active substance. When the herbicidal active substance is formulated into an emulsifiable concentrate, the antidote reduces the bleaching of cultivated plants while maintaining good herbicidal action (see Tables I and II). When the herbicidal active substance is formulated into microcapsules, the antidote maintains a low bleaching value of cultivated plants while increasing or maintaining the herbicidal action on weed plants (see Tables XIII and XIV).

The active ingredients are processed into a form that is suitable for direct use in the treatment of cultivated and weedy plants. The active ingredient can be the antidote itself or a mixture of herbicidally active ingredient and antidote. The purpose of the treatment agent is to apply the active ingredients to the place where they are needed to achieve herbicidal selectivity by conventional methods. This place is always understood to mean soil, seeds, seedlings and plants.

Compositions include regular powders, wettable powders, granules, solutions and emulsifiable concentrates.

Powders are free-flowing powder compositions containing the active ingredient supported on a carrier in particulate form. The particle size of the carrier is generally about 30 to 50 microns. Examples of suitable carriers include talc, bentonite, diatomaceous earth and pyrophyllite. The composition generally contains 50% of the active ingredient. Anti-caking and anti-static additives may also be added. The powders may be applied by arm- or hand-held sprayer or from an aircraft.

Wettable powders are finely divided compositions comprising a carrier in the form of particles with applied active ingredients and additionally at least one surfactant. The surfactant enables the powder to be rapidly dispersed in an aqueous medium to form stable, sprayable suspensions. A wide variety of surfactants may be used, such as long-chain fatty alcohols and alkali metal salts of sulfated fatty alcohols, salts of sulfonic acids, esters of long-chain fatty acids, polyhydric alcohols with free alcohol groups, and relatively long-chain omega-substituted polyethylene glycols. A review of surfactants suitable for use in agricultural compositions is given in Wade Van Valkenburg, Pesticide Formulation (Marcel Dekker, Inc., N. Y., 1937) pp. 79-84.

Granules contain the active ingredient supported on an inert carrier, which is in the form of particles having a diameter of 1 to 2 mm. Granules can be produced by spraying a solution of the active ingredients in a volatile solvent onto the granular carrier. Examples of suitable carriers for the production of granules include clay, vermiculite, wood chips and granulated carbon.

Emulsifiable concentrates are oil solutions of the active ingredient and an emulsifier. Before use, the concentrate is diluted with water to form a suspended emulsion of oil droplets. The emulsifiers used are usually mixtures of anionic and nonionic surfactants. Emulsifiable concentrates may also contain other additives such as suspending agents and thickeners.

If an antidote and a herbicidally active substance are used as active substances, the ratio of antidote to herbicidally active substance is generally approximately 0.001 to 30 parts by weight of antidote per part by weight of herbicidally active substance.

The compositions generally contain some additives in addition to the active ingredients and carriers. These include, for example, inert substances, diluents, organic solvents, water, oil and water, water-in-oil emulsions, powder and granule carriers and surfactants, wetting agents, dispersants and emulsifiers. The compositions may also contain fertilizers, for example ammonium nitrate, urea and superphosphate. They may also contain rooting and growth promoting substances, for example compost, manure, humus and sand.

The compounds with antidote function and the herbicidally active substances and compositions containing antidote according to the invention can also be used to treat cultivated plants by adding them to the irrigation water used for the treated plot. This method allows the penetration of the active substances into the soil absorbing the irrigation water.

The active ingredients can also be applied to the soil in the form of a solution in a suitable solvent. Commonly used solvents for this purpose are kerosene, fuel oil, xylene, petroleum fractions rich in methylated naphthalenes. Liquid solutions, as well as powders, can be applied by spraying with a boom or hand sprayer or from aircraft.

Claims (4)

Subject What is claimed is: 1. A herbicidal composition with a crop protection agent which comprises a herbicidally effective amount of a pyrrolidone compound of the formula (I): X is hydrogen, chlorine or methyl, Y is hydrogen, chlorine or bromine, Z is chlorine or bromine; R is hydrogen, C1-C4alkyl inclusive, acetyl, chlorine, bromine, fluorine or iodine, trifluoromethyl, nitro, cyano, C1-C4alkoxy inclusive, C1-C4alkylthio inclusive C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamide or 3-methylureido, R1 is a hydrogen atom, a C1-C4 alkyl group inclusive, a chlorine atom or a trifluoromethyl group of the invention R 2 is C 1 -C 4 alkyl, inclusive, or hydrogen, and a non-phytotoxic anti-toxic effective amount of a compound of Formula II About R3 II / ChCHC — N \ Where does that mean R 5 is ethyl or allyl, R 8 is a benzyl or allyl group, or R 3 and R 6 together with the nitrogen atom to which they are attached form a 2,2,5-trimethyl-1,3-oxazolidine group at a weight ratio of the antidote of formula II to the pyrrolidone compound of formula I of 0.001: 1 to 30: 1. 2. A herbicidal composition as claimed in claim 1, wherein X is hydrogen, Y is chlorine, Z is chlorine, R1 is trifluoromethyl, R1 is hydrogen and R2 is hydrogen. 3. The herbicidal composition of claim 1, wherein the pyrrolidone compound is formulated as an emulsifiable concentrate. 4. The herbicidal composition of claim 1, wherein the pyrrolidone compound is formulated as microcapsules.