MXPA97005131A - Herbicidal compositions of 4-benzoylosoxazol oherbicides 2-ciano-1,3-diona and its antido - Google Patents

Abstract

The present invention relates to herbicidal compositions containing 4-benzoylisoxazole or 2-cyano-1,3-dione compounds and the antidote compounds of these to reduce the damage to various crops, particularly to maize, from the phytotoxic effects of the herbicides of 4-benzoylisoxazole or 2-cyano-1,3-dione when used alone or in combination with additional pesticidally active ingredients. Also disclosed are methods for reducing phytotoxicity or damage to crop plants, particularly corn crops, due to the herbicides of 4-benzoylisoxazole or 2-cyano-1,3-dio

Description

HERBICIDAL COMPOSITIONS OF 4-BENZOILOSOXAZQL Q HERBICIDES 2-CYAN-1, 3-PIONA AND ITS ANTIDOTES This invention relates to herbicidal compositions and methods of use and, more particularly, to certain herbicidal compositions comprising 4-benzoylisoxazole or 2-cyan-1,3-dione compounds and its antidotes which are useful as herbicides. A herbicide is a compound that adversely controls or modifies the growth of plants, for example, by killing, retarding, defoliating, drying, regulating, atrophying, spreading, stimulating and preventing their growth. The term plant refers to all physical parts of a plant, including seeds, seeds, sampling, roots, tubers, stems, petioles, foliage and fruits. "Plant growth" includes all stages of development from germination of the seed to the natural or induced term of life. Germicides are generally used to control or eradicate weed pests. They have gained a high degree of commercial success because it has been shown that such control can increase the yield of the crop and reduce harvesting costs. The most popular methods of herbicide application include: incorporation of the pre-plant into the soil; application in furrow to the seeds and surround them with earth; pre-emergence surface treatment of the sown soil; post-emergency treatment of the plant and soil; and treatment of the pre-plant seed. A manufacturer of herbicides generally recommends a range of reasons and application concentrations calculated to maximize control of the weed. The range of ratios ranges from about 0.01 to 50 Ib per acre (0.0111 to 56 kg per hectare) and is usually in the range of 0.1 to 25 Ib per acre (0.112 to 28 kg / ha). The term "herbicidally effective amount" describes an amount of a herbicidal compound that controls or adversely modifies the growth of plants. The actual amount used depends on several considerations, including susceptibility of the weed in particular and overall cost limitations. An important factor that influences the usefulness of a given herbicide is its selectivity towards crops. In some cases, a beneficial crop is susceptible to the effects of the herbicide. In addition some herbicidal compounds are phytotoxic to some weed species but not to others. To be effective, a herbicide must cause minimum damage ipreferamente no damage) to the beneficial crop while maximizing the damage to the weed species that infest the site of the harvest.

To preserve the beneficial aspects of the herbicide used and to minimize damage to crops, many herbicide antidotes have been prepared. These antidotes reduce or eliminate damage to crops without substantially imparting the harmful effect of the herbicide on weed species. See, for example, U.S. Patent Nos. 4,021,224, 4,021,229 and 4,230,874. The identification of an antidote that saves a herbicide in crops is a highly complicated task. The mechanism by which an antidote reduces herbicide damage to the crop has not been established. An antidote compound can be an interferential, protective or antagonistic remedy. As used herein, "antidote" describes a compound that has the effect of establishing herbicidal selectivity, i.e., continued herbicidal phytotoxicity toward the weed species by the herbicide, and reduced or zero phyloxicity to the cultivated species of the crop. The term "antidotally effective amount" describes an amount of an antidote compound that contracts up to the point. grade . to a phytotoxic response from a beneficial crop to a herbicide. The 4-benzoylisoxazole and 2-cyano-l, 3-dione compounds have been found to be very effective herbicides with broad and general herbicidal activity against many-leaf and grass weeds by pre- and / or post-emergence application. The method of controlling vegetation with these compounds comprises applying a herbicidally effective amount of the compounds with an inert carrier or diluent., to an area where herbicide control is desired. However, the herbicidal compounds of 4-benzoylisoxazole and 2-cyano-1,3-dione have been found in some cases to adversely affect or interfere with the cultivation of crop plants, especially corn crops. Therefore the effective use of these herbicides to control the weed in the presence of such crops is further improved by or may require in many cases, the addition of an antidotally effective amount of a compound, which is antidotally effective with the herbicide. . It has been found that some compounds when used in an antidotally effective amount are effective antidotes for the protection of crops, especially corn crops from adverse herbicide damage or adverse herbicide reduction caused by the use of a herbicidally effective amount of a compound of 4-benzoylisoxazole and 2-cyano-l, 3-dione. It is therefore an object of the present invention to provide compositions of 4-benzoylisoxazole and 2-cyano-1,3-dione herbicides in combination with their antidotes, said compositions being useful for reducing crop damage, especially corn, due to to the phytotoxicity of these herbicides.

The present invention relates to herbicidal compositions comprising herbicidal compounds of 4-benzoylisoxazole and 2-cyano-1,3-dione and their antidotal compounds to reduce damage to various crops, particularly corn, from the phyto-oxidizing effects of such herbicides. 4-benzoylisoxazole and 2-cyano-l, 3-dione when used alone or in combination with other compounds as co-herbicides. More particularly, the invention relates to a composition comprising: (a) (i) a 4-benzoylisoxazole herbicide, or an agriculturally acceptable salt thereof; (ii) a herbicidal compound of 2-cyano-1,3-dione, or an agriculturally acceptable salt thereof; and (b) an anotadically effective amount of an antidote compound which is antidotally effective with the herbicidal compound (a). The invention also relates to methods for reducing phytotoxicity or damage to crop plants, particularly corn crops due to a 4-benzoylisoxazole compound and 2-cyano-1,3-dione, or the salt thereof, when applied an antidotally effective amount of an antidote compound to the soil, crop or crop seed. The herbicidal 4-benzoylisoxazole compounds useful in the present invention are described in U.S. Patent Nos. 5,371,063, 5,371,064 and 5,374,606 and in European patent publications nos. 0 418 175, 0 487 357, 0 527 036 and 0 527 037, the disclosure of which is incorporated herein for reference thereto. The herbicidal 4-benzoylisoxazole compounds for use in this invention can be prepared by the methods described in the aforementioned patent publications, or by the application and adaptation of known methods used or described in the chemical literature. Many herbicidal 4-benzoylisoxazole compounds useful in this invention fall within the general formula ... (D wherein R represents a hydrogen atom, a halogen atom, a straight or branched chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms which is optionally substituted by 1 or more halogen atoms; a cycloalkyl group containing from 3 to 6 carbon atoms optionally substituted by one or more -R5 groups, one or more halogen atoms or a CCuR3 group, or a group selected from -C02R3, -COR ", cyano, nitro or -CONR3R4 R: represents a straight or branched chain alkyl, alkenyl or alkynyl group containing up to 6 carbon atoms which is optionally substituted by one or more halogen atoms, or a cycloalkyl group containing from 3 to 6 carbon atoms optionally substituted by one or more groups R 'or one or more halogen atoms R represents a halogen atom, an alkyl, alkenyl, aikinyl or straight or branched chain alkoxy group containing up to 6 carbon atoms, which is substantially substituted by one or more groups -OR5 or one or more halogen atoms; or a selected group of nitro, cyano, COR, -S? O) pR '"f -O (CH2) JTTOR5, -COR5, -NR61r62, -N (R8) S02R7, -OR5, -OSO R, -SNR -R ", -CONR'R", -CSNR3R4 and - (CR9R10) tS (O) qR7; n represents an integer from one to five, wherein n is greater than one, the R- groups may be the same or different; R 'and R' each represents a hydrogen atom, a straight chain or branched alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms; R: represents an alkyl group of straight or branched chain containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms, a straight or branched chain alkenyl or alkynyl group containing from 3 to 6 carbon atoms, the which is optionally substituted by one or more halogen atoms, or optional phenyl er.re replaced by one to five R2 groups which may be the same or different, R ', Rhl and R:', the ales can be the same or different, each represents a straight or branched chain alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more carbon atoms; or phenyl optionally substituted by one to five R2 groups, which may be the same or different; R; represents a straight or branched chain alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms; phenyl optionally substituted by one to five R2 groups, which may be the same or different; or a halogen atom; R "represents a hydrogen atom, a straight or branched chain alkyl, alkenyl or alkynyl group containing up to ten carbon atoms, which is optionally substituted by one or more halogen atoms, a cycloalkyl group containing from three to six carbon atoms, phenyl optionally substituted by from one to five groups, which may be the same or different, selected from halogen, nitro, ciapo, R5, -S (0) pr5 and -OR5, or a group selected from -S02R ' and -OR5; R 'and Rlu, which may be the same or different, each represent a hydrogen atom, a straight or branched chain alkyl group containing up to six carbon atoms, which is optionally substituted by one or more halogen atoms, or phenyl optionally substituted by one to five R ~ groups, which may be the same or different, R and R-, which may be the same or different, each represents a hydrogen atom; caden alkyl group straight or branched containing up to 6 carbon atoms, which is substantially substituted by one or more halogen atoms; p represents zero, one or two; q represents zero, one or two; m represents one, two or three; t represents an integer from one to four; When t is greater than one, the groups -CR9R1: - may be the same or different; or an agriculturally acceptable salt thereof, which possesses herbicidal properties.

In some cases, groups R to R10, R51, R52, R € 1 and R62 can give rise to optics and / or stereoisomerism. All these forms are encompassed by the present invention. The term "agriculturally acceptable salts" means the salts of the cations or anions which are known and accepted in the art for the formation of salts for agricultural or horticultural use. Preferably the salts are soluble in water. Suitable acid addition salts, formed by the compounds of the formula (I) containing an amino group, include salts with inorganic acids, for example, hydrochlorides, sulfates, phosphates and nitrates and salts with organic acids, for example, acetic acid. Suitable salts formed by the compounds of the formula (I) which are acidic, ie the compounds containing one or more carboxy groups, with bases including alkali metal salts, (for example sodium and potassium), metal salts alkaline earth (for example, calcium and magnesium), and amine salts (for example, distanol amine, triethanolamine, octylamine, dioctylmethylamine and orpholine). A preferred class of compounds of the formula (I) are those having the formula where. R, R1, R2, R7, R9, R10, N, q and t have two meanings disclosed above. In a further embodiment wherein n is less than one, the benzoyl ring of the compounds of the formula (la) is 2, -disubstituted or 2, 3, 4 -trisubstituted. The compounds of the formula (la) in which n is greater than one and the benzoyl ring of the compound of the formula la is 2,3-disubstituted are also preferred. A further preferred class of the compounds of the formula (la) are those wherein: R is hydrogen or -C02Et; R1 is cyclopropyl; R ^ is a halogen atom or a group selected from -CFJ (-S (0) pMe and -OMe; n is one, two or three; t is one; R; is a straight or branched chain alkyl or alkenyl group; , containing more than four carbon atoms optionally substituted by one to three fluoride atoms, or is phenyl; R "is hydrogen or methyl; R10 is hydrogen; and p and q, which may be the same or different, each is zero, one or two Another preferred class of compounds of the formula (I) are the compounds having the formula wherein R, R:, R2, R7 and n have the given meaning "disclosed above." A further preferred class of the compounds of Formula (Ib) are those wherein R is hydrogen, R1 is ethyl or cyclopropyl, R2 is halogen n is one or two, and R7 is methyl, ethyl or -NMe ,.

Another preferred class of compounds of the formula (I) are those having the formula wherein X is oxygen or -S (0) q-; z is zero or an integer from one to five; and R, R1, R2, R7 and n have the meaning disclosed above. A preferred class of the compounds of the formula (le) are those in which one of the substituents of the benzoyl ring is in the 2-position. Other preferred compounds of the formula (le) are those in which the 5 and / or 6 position of the The benzoyl ring is unsubstituted, more specifically preferred that both positions 5 and 6 are unsubstituted. A further preferred class of the compounds of the formula (le) are those wherein R 1 is a cyclopropyl group; R2 is halogen or a group selected from methyl, trifluoromethyl, methoxy, and -S (0) rRr; where n is two or three; X is -S (0) q-; R7 is halogen or a group selected from methyl, trifluoromethyl, nitro, and -OR5; R5 is methyl or ethyl; and R6 is methyl. An additional preferred class of compounds of the formula (I) are those given by the formula wherein: R 1 is a methyl, ethyl, isopropyl, cyclopropyl or 1-methylcyclopropyl group; R "is a chlorine, bromine or fluorine atom, or a straight or branched chain alkyl or alkoxy group containing up to four carbon atoms: R" is hydrogen atom, chlorine, bromine or fluorine; a group selected from R5, -C02R5 and -ORs; or a straight or branched chain alkyl or alkoxy group containing up to four carbon atoms substituted by -0RS; R1 * is -S (0) f) R *; RB is a straight or branched chain alkyl group containing up to four carbon atoms which is optionally substituted by one or more halogen atoms; R 'is a methyl or ethyl group; and p is zero, one or two; A specifically preferred class of the compounds of the formula (I) has the formula wherein R2S is chloro, bromo or trifluoromethyl. Due to their herbicidal properties, the compounds of the formula (I) wherein R 1 is substituted or unsubstituted with cyclopropyl are particularly preferred for use in the compositions of the present invention. The following compounds are known among the most preferred 4-benzoylisoxazole compounds for use in the present invention: 5-cyclopropyl-4- [2-chloro-e-ethoxy-4- (ethylsulfonyl) be zoyl] isoxazole; 4- (4-chloro-2-methylsulfonylbenzoyl) -5-cyclopropylisoxazole; 5-cyclopropyl-4- (2-methylsulfonyl-4-trifluoromethylbenzoyl) -isoxazole; and 4- (4-bromo-2-methylsulfonylbenzoyl) -5-cyclopropylisoxazole. The 2-cyano-1,3-dione herbicidal compounds useful in the present invention are described in European Patent Publication Nos. 0496 630 and 0 496 631, the disclosure of which is incorporated herein by reference. The herbicidal 2-cyano-l, 3-dione compounds for use in this invention can be prepared by the methods described in the aforementioned patent publications, or by the application and adaptations of known methods used or described in the chemical literature .

Many of the herbicidal 2-cyano-l, 3-dione compounds useful in the present invention fall within the general formula wherein: Rr "is a straight or branched chain alkyl group containing up to six carbon atoms, which is optionally substituted by one or more halogen atoms, which may be the same or different, or a cycloalkyl group containing three to six carbon atoms, which is optionally substituted by one or more groups selected from R55 and one or more halogen atoms which may be the same or different, one of R51 and Rr "J is -S (0) rR56 and the other of R51 and R53 is a halogen atom; a hydrogen atom; a straight or branched chain alkyl group containing up to six carbon atoms which is substituted by -OR55; -R55; nitro; cyano; -SR55; -0R: ":; -O (CH :.) sOR- =; o -COrR"; R 'and RJ, which may be the same or different, each is a halogen atom; a hydrogen atom a straight or branched chain alkyl group containing up to six carbon atoms which is substituted by -OR55; -RS5; nitro; spout; -OR "; -0 (CH,) OR; or -C02R55; R and R" 1, which may be the same or different each is a straight or branched chain alkyl group containing up to six carbon atoms which may be be optionally substituted by one or more halogen atoms, which may be the same or different; s is an integer from one to three; and r is zero, tno or two; and where the compounds exist in enolic tautomeric forms, their agriculturally acceptable salts, which possess valuable agricultural properties. The compounds of the formula (II) may exist in tachygenic enolic forms which may develop into geometric isomer forms around the enolic double bond. Additionally, in some cases, the substituents R50, R51; R52; R53; R "; R and R5" may contribute to optical isomerism and / or stereoisomerism. All these forms are comprised within them of 2-cyano-l, 3-dione compounds in the present invention. This invention comprises a two-part herbicidal system comprised of: (a) a herbicide of 4-benzoylisoxazole and 2-cyano-l, 3-dione as described above and (b) an effective antidote thereto. It has been discovered that such antidotal compounds can be selected from a wide range of chemicals that have been found to be effective as herbicide antidotes to the 4-benzoyl isoxazole herbicides described above. Preferred compositions of this invention may include one or more such antidotes with the herbicides. The variety of crops in which the above-described herbicides are used can be significantly expanded by the use of an antidote to protect one or more of the harvests from damage to them and make the composition more selective against the weed. Some of such important types of antidotes are amides or haloalkane acids, aromatic oxime derivatives, thiazole carboxylic acids and their derivatives and 1,8-naphthalic anhydride. Preferably the compositions of the present invention comprise an antidotally effective amount of (i) a compound of the formula (? DII wherein R7 can be selected from the group consisting of haloalkyl, haloalkenyl, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, halogen, hydrogen, carboalkoxy, N-alkenylcarbalalkyl, N-alkenylcarbamyl, N-alkyl-N-alkynylcarbamyl; -alkyl-N-alquinilcarbamilalquil; N-alquenilcarbamilalcoxialquil; N-alkyl-N-alquinilcarbamilalcoxialquil; alkynoxy; haloalkoxy tiocianatoalquil; alquenilaminoalquil; cyanoalkyl alquilcarboalquil; cianatoalquil; alkylthioalkyl alquenilaminosulfonalquil; haloalquilcarboniloxialquil to lcoxicarboalqui 1; Haloa lqueni lcarboni loxialqui 1 hidroxihaloalquiloxialquil; hidroxialquilcarboalquiloxialqui1 hydroxyalkyl; alcoxisulfonoalquil; furil; thienyl alkyldiothiolenyl;; phenyl; substituted phenyl wherein the substituents may be selected from halogen, alkyl, haloalkyl, alkoxy, carbamyl, nitro, carboxylic acids, and their salts, and haloalkylcarbamyl; phenylalkyl; phenylhaloalkyl; phenylalkenyl; substituted phenylalkenyl, wherein the substituents may be selected from halogen, alkyl, alkoxy, and halofenoxy, phenylalkoxy; phenylalkylcarboxyalkyl phenylcycloaikyl; halophenylalkenoxy; halothiophenylalkyl halofenoxyalkyl; bicycloalkyl; alkenylcarbamylpyridinyl alkynylcarbamylpyridinyl; dialkenylcarbamylbicycloalkenyl and alkynylcarbamylbicycloalkenyl; R- and R7, which may be the same or different, are selected from the group consisting of alkenyl; haloalkenyl; hydrogen; alkyl; haloalkyl; alkynyl; cyano alkyl; hydrox. alkyl; hydroxyhaloalkyl haloalkylcarboxyalkyl; alkylcarboxyalkyl alkoxycarboxyalkyl; ioalkylcarboxyalkyl; alkoxycarboalkyl alkylcarbamyoxyalkyl; Not me; formyl; haloalkyl-N-alkylated; haloalkylamido; haloalkylamidoalkyl haloalkyl-N-alkylamidoalkyl; haloalkylamido-alkenyl alkylimido; cycloalkyl; alkylcycloalkyl; alkoxyalkyl alkylsulfonyloxyalkyl; ercaptoalkyl; alkylaminoalkyl alkoxycarboalkenyl; haloalkylcarbonyl; alkylcarbonyl alkenylcarbamyoxyalkyl; cycloalkylcarbamyoxyalkyl-alkoxycarbonyl; haloalkoxycarbonyl; halof enylcarbamyoxyalkyl cycloalkenyl; substituted phenyl / phenyl wherein the substituents may be selected from alkyl, halogen, haloalkyl, alkoxy, haloalkylamido, phthala, hydroxy, alkylcarbatoxy, alkenylcarbamyloxy, alkylamido, haloalkylamido and alkylcarboalkenyl; f-enylsulfonyl; f-substituted alkylalkyl; wherein said substituents may be selected from halogen or alkyl; dioxyalkylene; halof enoxyalkylamido-alkyl; alkylthiodiazolyl; piperidyl; piperidylalkyl; dioxolanialkyl; thiazolyl; alkylthiazolyl; benzodiazolyl; halobenzothiazolyl, • furyl; furil substituted with alkyl; furilalkyl; pyridyl; alkylpyridyl; alkoxazolyl; tetrahydrofuryl alkyl; 3-cyanothienyl; tinyl substituted with alkyl; 4,5-polyalkylene thienyl; alfa- ha l o a l i l a c a t a m i d o f a n i l a l i l; a l f a -haloalqui lacetamidonitrof eni lalqui l; f-haloalkylacetate idohalcf enylalkyl and cyanoalkenyl; or R and R '~ when taken together can form a structure consisting of piperidinyl; alkylpiperidinyl pyridyl; di- or tetrahydropyridinyl; alkyltetrahydropyridyl orfolyl; azabicyclononyl; diasacicloalkanyl benzoalkylpyrrolidinyl; oxazolidinyl; perhydrooxazolidinyl alkyloxazolidinyl; f ryloxazolidinyl; thienyl oxazolidinyl pyridyloxazolidinyl; pyrimidinyloxazolidinyl benzooxazolidinyl; Z, _? spiromocycloalkyl-oxazolidinyl alkylaminoalkenyl; Alkylideneimino; pyrrolidinyl piperidonyl; perhydroacepinil; perhydroazocinil; pyrazolyl dihydropyrazolyl; p: .perazinyl; perhydro-1,4-diazepinyl quinolinyl; isoquinclinil; dihydro-; tetrahydro-; or perhydroquinolyl or isoquinolyl; indolyl or di- or perhydroindolyl; and whose combined members R71 and R72 can be substituted with those independent radicals 71 and 72 listed above; or (ii) one of the following compounds: OÍ- [(cyanomethoxy) irnino] benzeneacetonitrile; a- [(1,3-dioxolan-2-ylmethoxy) imino] -benzeneacetonitrile; 0- [3-dioxolan-2-ylmethyl] -2,2, 2-trif luoromethyl-4'-chloroacetof enonaoxime; benzenemethamine, 'N- [4 - (dichloro ethylene) -1, 3-diotolan-2-ylidene] -or-methyl, hydrochloride; acetic acid diphenylmethoxy, methyl ester; 1,8-naphthalic anhydride; cloquintocet; , 6-dichloro-2-phenylpyrimidine; 2-Chloro-N- [1- (2,4,6-trimethylphenyl) ethenyl] aceta-ida; and ethylene glycol 1,1-dichloroacetone acetate. Antidote amides of alkanoic acids of the formula (III), which include those in which nitrogen forms a portion of a heterocyclic ring with substituents, are described in a number of publications such as U.S. Patent Nos. 4,021,224, 4,256,481, 4,294,764 and 5,201,933 and British Patent 1,521,540. The North American patent no. No. 4,021,224 contains a wide disclosure of such types of compounds and indicates many possibilities for mono- or di-substitution at the hydrogen atom. A group of preferred antidotal compounds includes those according to formula (III), wherein R70 is haloalkyl C, ,, R7i and R7"are independently alkenyl or haloalkyl. C,", or 2,3-dioxolan-2- il-methyl and R71 and R72 when combined form a saturated or unsaturated heterocyclic ring containing O, S and / or N atoms and which may be substituted with alkyl, haloalkyl, alkoxy, alkoxyalkyl or haloacyl groups of one to five atoms The preferred haloalkyl R-member of the formula (III) is dichloromethyl The preferred species in this group of antidotal compounds are N, N-diallyl-dichloroacetamide and N- (2-propenyl) -N- (1, 3 -dioxolanyl-methyl) dichloroacetamide Even more preferred antidote compounds according to formula (III) are a group of dichloroacetamides substituted with 1,3-oxazolidinyl or thiazolidinyl having the formula where Y is oxygen or sulfur; R '\ R7, R ~ "\ R7', R77 and R7ß, are independently hydrogen, alkyl, alkyloyl, haloalkyl or C1-4alkoxy; C2_alkoxyalkyl;" C12_alkylthio; C1-4alkyl; alkylsulfonylmethyl C1-;; a bicyclic hydrocarbon radical having up to ten carbon atoms; phenyl; or a saturated or unsaturated heterocyclic radical having a ring atom C4-? or Y <3 containing atom (s) of O, S, and / or N wherein the phenyl and heterocyclic radicals are optionally substituted with one or more C 1-4 alkyl radical, haloalkyl C 1-4, C 1 alkoxy, C 2 alkoxyalkyl, halogen or nitro, or R73 and R74 together with the carbon atom. to which they are attached form a group of spirocycloalkyl C, optionally substituted by one or more methyl groups Preferred members according to the formula (IV) are those wherein R7 ', R77 and R78 are hydrogen, R75 is hydrogen, methyl, pheni, or a heterocyclic radical; and R73 and R74 are independently methyl or trifluoromethyl or when taken together with the carbon atom to which they are attached, they form a cycloalkyl radical with five or six carbon atoms. Oxime derivatives which are suitable for use as antidotes with herbicides are disclosed, for example, in U.S. Patent Nos. 4,070,389 and 4,269,775 and have the general formCN \ C = N0CH2RQ1 / Ar in which Ar is a phenyl or substituted phenyl wherein the substituents are optionally methyl, methoxy, chloro, cyano or trifluoromethyl, or Ar is a naphthyl radical; R91 is cyano, - (Rc) (Rd), or -CN (R (R,), where R, and R, are independently lower alkyl or together with the carbon atom form a heterocyclic ring with 5- or 6- members containing oxygen or sulfur, which is substituted by lower or unsubstituted alkyl, halogen and / or nitro; (Rc) and (Rd) are independently hydrogen, lower alkyl, cycloalkyl, which are unsubstituted or additionally substituted with one or more of halogen, lower alkoxy and / or cyano; (Rg) and (Rh) together with the nitrogen form a 5 or 6 membered ring which is unsubstituted or mono- or poly-substituted by halogen, cyano and / or lower alkyl and which may to be interrupted by a nitrogen, oxygen or sulfur atom Representative compounds of this type are those in which R19 is cyano, and in which R91 is 1,3-dioxolan-2-yl The last compound has the chemical name O - [2- (1,3-dioxolanyl) methyl] alpha-cyanobenzaldoxime The thiazole carboxylic acids and their appropriate derivatives for use as antidotes are disclosed in US Pat. No. 4,199,506 and have the general formCR ^ CC = -C (0) R "NS \ 0. Ry4 in which R" ~ is alkyl, haloalkyl or trialcoxymethyl; R93 is variously hydrogen, agriculturally acceptable cations or various hydrocarbyls or substituted hydrocarbyl groups; is 0 or 1; and R'4 is chloro, iodo, lower alkoxy or substituted or unsubstituted phenoxy. A representative member of this class is the benzyl-2-chloro-4-trifluoromethyl-methyl-5-thiazole carboxylate compound (R92 = trifluoromethyl; R93 = benzyl, R94 = chloro; = 1). Another useful herbicidal compound is disclosed in European Patent No. 0104495 having the formula wherein R., "is haloalkoxy C, -C. containing from 1 to 3 halogen atoms or an optionally substituted phenyl group; R96 represents a hydrogen atom, a methyl or a phenyl; R97 represents an alkyl group, a C5-C6 cycloalkyl group, a cyclohexylmethyl group, an optionally substituted phenyl group, an optionally substituted benzyl group, a propargyl group; and n is zero or one. A representative group of that group could be: CH3 N X '' CH2COOCH3 Especially preferred antidotes for use in the present invention include: 2,2,2-trimethyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5-f-enyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5- (2-thienyl) -N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5- (2-thienyl) -N-dichloroacetyl, N, N-diallyl-dichloroacetamide oxazolidine; 2, 2-spirocyclohexyl-N-dichloroacetyl oxazolidine; 2,2-dimethyl-N-dichloroacetyl oxazolidine; 4- (dichloroacetyl) -3,4-dihydro-3-methyl-2H-1,4-benzoxazine; 3- [3- (dichloroacetyl) -2, -dimethyl-5-oxalidinyl] pyridine; 4- (dichloroacetyl) -l-oxa-4-azapiro- (4,5) decane; 2, 2-dichloro-l- (1,2,3,4-tetrahydro-l-methyl-2-isoquinolyl) ethanone; cis / trans-1,4-bis (dichloroacetyl) -2,5-dimethylpiperazi; N- (dichloroacetyl) -1, 2, 3,4-tetrahydroquinaldine; 1,5-bis (dichloroacetyl) -1,5-diazacyclononane; 1- (cyclooacetyl) -1-azaspiro [4, 4] nonane; a- [(cyanomethoxy) imino] benzeneacetonitrile; - [(1,3-dioxolan-2-ylmethoxy) imino] benzene acetonitrile; O- [1,3-dioxolan-2-ylmethyl] -2,2,2-trifluoromethyl-4'-chloroacetophenone oxime; benzene e t amine, N- [4- (dichloromethylene) -1,3-diotolan-2-ylidene] -a-methyl; hydrochloride; acetic acid of dif enllmetoxy, - meti. ester; 1, 8-naphthalic anhydride; 4,6-dichloro-2-p-enylpyrimidine; 2-chloro-N- [1-2,4,6-trimethylf-enyl) ethenyl] -acetamide; cloquintocetic; and ethylene glycol acetal of 1,1-dichloroacetone. The herbicidal compositions according to this invention may also contain one or more additional pesticidally active ingredients. Herbicides that can be used as co-herbicides with the 4-benzoylisoxazole or 2-cyan-1,3-dione compounds of the formula (I) with the benefit in combination with an antidote as described herein, preferably include thiocarbamates (including dithiocarbamates), α-haloacetamides, phenyl heterocyclyl ethers, imidazoline, pyridines and sulfonylureas. It is within the scope of this invention that other classes of herbicides, for example, triazines, ureas, diphenyl ethers, nitroanilines, thiazoles, pyrrolidinones, aromatic and heterocyclic di- and tri-ketones, etc., the individual members of whose classes can be derived have one or more substituents selected from a variety of radicals can be used co-co-herbicides appropriately. Such combinations can be used to obtain selective control of weeds with little damage to crops in several crop plant varieties such as corn, sorghum, and cereals such as wheat, rice, barley, oats, and rye, as well as several varieties. of crops? and oily seeds such as soybeans and cotton. Insecticides such as synthetic pyrerethroids and fungicides such as carbamates and triazoles, may also be included in the herbicidal compositions of this invention. Effective control of weed coupled with low crop damage is the result of treatment of a plant site with a combination of a 4-benzoylisoxazole compound or 2-cyano-1,3-dione and an antidote compound according to the present invention. By application to the "plant site" means the application to the growth medium of the tai plant as the soil, as well as seeds, emerging seeds, roots, stems, leaves, or other parts of the plant. The phrase "combination of a 4-benzoylisoxazole compound or 2-cyano-1,3-dione and an antidote compound" includes various methods of treatment. For example, the soil of a plant site can be treated with a "tank mix" composition that contains a mixture of the herbicide and the antidote that is "in combination". 0, the soil can be treated with the herbicide and antidote compounds separately in such a way that the "combination" is made, on or in the soil. After such treatments if the soil with a mixture of herbicide and antidote or by a sequential or separate application of the herbicide or antidote to the soil, the herbicide and the antidote can be mixed in or incorporated into the soil either by mechanical mixing of the soil with implements or by "wetting" by rain or irrigation. The soil of a plant site can also be treated with the antidote by applying the antidote in a dispersible form -concentrated, such as a granule. The granule can be applied to the furrow which is ready to receive the harvest seed and the herbicide can be applied to the plant site either before or after the placement in the granule zureo containing the antidote for the herbicide and the antidote form a combination. The crop seed can be treated or coated with the antidote compound either while the harvest seed is in the zureo just after sowing it or, more commonly the harvest seed can be treated or coated with antidote before germinating in a zureo. The herbicide can be applied to the soil site of the plant before or after it germinates and becomes "a combination" when both the herbicide and the seed coated with antidote are in the soil. Also referred to as "a combination" • is a commercially convenient association or presentation of herbicide and antidote. For example, the herbicidal and antidote components in concentrated form may be contained in separate containers, but such containers may be presented to be sold or purchased together as "a combination". 0, the herbicide and antidote components in concentrated form can be in a mixture in a single container as "a combination". Whether such a "combination" can be diluted or mixed with auxiliaries appropriate for soil applications. Another example of a combination presented, commercially is a single-seed crop container coated with antidote, or presented for sale together with a container of herbicidal material. This container may or may not be attached to each other, but nevertheless constitutes a combination of herbicide and antidote when it is intended for ultimate use in the same site of the plant. In the above description of the various modes of application of the herbicide-antidote combinations, it is inherent that each form of application requires in some way, that the herbicide and antidote be combined physically to form a "composition" of those agents. The amount of a particular herbicide of 4-benzoiiisoxazole or 2-cyano-l, 3-dione that is to be applied to the plant site or to a crop growth area will be varied with, among other things, the nature of the grass, the herbicide used in particular, the time of application, the climate and the nature of the harvest. The application rates of between approximately 0.01 kg / ha and 5.0 kg / ha of herbicide of 4-benzoylisoxazole or 2-cyano-l, 3-dione are generally appropriate, with a ratio of approximately 0.01 kg / ha to 4.0 kg / ha being preferred and from about 0.01 kg / ha to 2.0 kg / ha being especially preferred. The amount of a given antidote to be used in combination with the herbicide according to this invention and the manner of its use and resulting efficacy may vary according to various parameters, such as the particular antidote to be employed, the harvest which is going to be protected, the amount or reason of the herbicide that is going to be applied and the climatic conditions and the agricultural soil in which it is combined. it's going to be applied The selection of a specific antidote for use in the herbicide composition, the manner in which it will be applied (for example, mixing tank, zureo application, seed treatment, etc.), the determination of the activity, which does not it is phytotoxic but antidotally effective, and the amount necessary to provide this result can be easily performed using the test procedures in the cited patents, such as er. U.S. Patent No. 4,021,224, in accordance with common practice in the art. For other descriptions of antidotes and methods of use, reference is made to U.S. Patent No. 3,959,304; 3,989.5: 3-3,131,509; 3,564,768; 4,137,070; 4,294,764; 4,256,481; 4,415,353 and 4,415,352. The antidote is applied in combination with the herbicide in an antidotally non-phytotoxic amount. By "non-phytotoxic" is meant an amount of the antidote that causes at least some or less or no damage to the desired crop species. "Antidotally effective" FCR means an antidote used in an amount that is effective as an antidote with the herbicide to decrease the degree of damage caused by the herbicide to the desired crop species. The ratio of herbicide to antidote may vary depending on the crop to be protected, the weed to be inhibited, the herbicide used, etc., but usually a herbicide-to-antidote ratio is in the range of about 1:25 to 60: 1 parts by weight can be employed, although much higher antidote ratios can be used, such as, for example, 1: 100 to 1: 300 parts by weight of herbicide to antidote. The preferred weight ratio of herbicide to antidote is from about 1:10 to about 30: 1. Another weight ratio range is between about 1: 1 to 20: 1, with the weight ratio range about 2: 1 to 15: 1 even more preferred. In field applications, the antidote herbicide, or a mixture thereof, can be applied to the plant site without any auxiliary other than a solvent. Usually, the antidote herbicide or its mixture is applied together with one or more auxiliaries in liquid or solid form. Compositions or formulations containing mixtures of an appropriate herbicide and antidote are prepared by incorporating the herbicide and the antidote with one or more auxiliary agents, solvents, extenders, carriers, conditioners, water, wetting agents, dispersing agents, or emulsifying agents or any combination appropriate of these auxiliaries. These mixtures can be in the form of solid particles, granules, pills, powders, wettables, powders, solutions, aqueous dispersions or emulsions. The application of the herbicide, antidote, or mixtures thereof can be carried out by conventional techniques using, for example, hand or tractor mounted sprayers, dust dispersers, hand sprayers and spray dust and granular applicators. If desired, the application of the compositions of the invention to the plants can be carried out by incorporating the compositions in the soil or other medium. The following examples are for illustrative purposes only and are not intended as necessarily representative of all tests performed and are not intended to limit the invention in any way. As anyone with skill in the art is aware, in the herbicidal test, a significant number of factors that are not easily controllable can affect the results of individual tests and render them non-reproducible. For example, the results may vary depending on environmental factors, such as sunlight and water, type of soil, soil pH, temperature and humidity, among other factors. Also the depth of the plantation, the rate of application of the herbicide, the rate of application of the antidote and the ratio of application of herbicide to antidote, as well as the nature of the crops being tested, may affect the results of the test. . The results may vary from harvest to harvest within harvest varieties EXAMPLES The herbicidal compounds 5-cyclopropyl-4- [2-chloro-3-ethoxy-4 (ethylsulfonyl) benzoyl] -isoxazole ("Herbicide") and the antidote compound 2, 2, 5-trimethyl-N-dichloroacetyl oxazolidine ("antidote") were applied to (for reasons listed in Table I below) pre-emergence to aluminum superificies (measuring 9 cm wide x 20 cm long x 7 cm deep containing sandy ground marcja in which were the following species: Ipo oea hederacea (ivileaf morningglory) ("IPOHE"): Faberi taria (giant foxtail) ("SEFTA"); Tricum aes tivum 'Prinqual' ("Wheat"); Oryza sativa 'Katy' ("rice"), Zea mays 'Garst 8940' (corn) (Maize GA8532).) The soil was fortified with fertilizer (10-10-10 = before sowing) All the compounds applied were materials The compounds were dissolved in 50/50 water / acetone solution and applied with a carrier volume of 200 I / Hectare.All treatments were reproduced twice.

After application, the surfaces were placed in a greenhouse and kept under good growth conditions. The damage to the plants was evaluated 20 days after the treatment ("DDT"). The damage was evaluated as a percentage of control, the percentage of control being total damage to the plants due to all the factors: inhibited sprouting, stunting, malformation, albinism, chlorosis, and other types of plant damage. The control intervals from 0 to 100 percent, which were 0%, represented no effect on growth equal to the untreated control and when it was 100% the plant died completely. The results observed are summarized in Table I below.

Although the invention has been described with reference to the preferred embodiments and their examples, the scope of the present invention is not limited only to those embodiments described. As will be more apparent to those skilled in the art, modifications and adaptations may be made to the invention described above without departing from the spirit and scope of the invention, which is defined and circumscribed by the appended claims.

Claims (20)

1. CLAIMS 1. A herbicidal composition comprising: (a) a herbicidally effective amount of a herbicidal compound of 4-benzoylisoxazole or 2-cyano-1,3-dione, or an agriculturally acceptable salt thereof; and (b) an antidotally effective amount of an antidote compound which is antidotally effective with 4-benzoylisoxazole or 2-cyano-1,3-dione.
2. 2. The herbicidal composition according to claim 1, wherein component (a) is 4-benzoylisoxazole of the formula wherein, (~ R represents a hydrogen atom, a halogen atom, a straight or branched chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms, - a cycloalkyl group containing from 3 to 6 carbon atoms optionally substituted by one or more -Rs groups, one or more halogen atoms or a C02R3 group, or a group selected from -C02R3, -COR5, cyano, nitro or -CONR3R4 R1 represents a straight or branched chain alkyl, alkenyl or alkynyl group containing up to 6 carbon atoms which is optionally substituted by one or more halogen atoms, or a cycloalkyl group containing from 3 to 6 carbon atoms optionally substituted by one or more groups R5 or one or more halogen atoms R.sub.2 represents a halogen atom, an alkyl, alkenyl, alkynyl or straight or branched chain alkoxy group containing up to 6 carbon atoms, the ual is optionally substituted by one or more groups -OR5 or one or more halogen atoms; or a selected group of nitro, cyano, -C02R3, -S (0) pR6, -OÍCH ínOR5, -COR5, -NR ^ r62, -N (R8) S02R7, -OR5, -OS02R7, -S02NR3R4, -CONR3R4, -CSNR3R4 and - (CR9R10) tS (O) qR7; n represents an integer from one to five; wherein n is greater than one, the R2 groups may be the same or different; R3 and R4 each represents a hydrogen atom, a straight or branched chain alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms, - R5 represents a straight chain alkyl group or branched containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms; a straight or branched chain alkenyl or alkynyl group containing from three to six carbon atoms, which is optionally substituted by one or more halogen atoms; or phenyl optionally substituted by one to five R2 groups which may be the same or different; R6, RS1 and R65, which may be the same or different, each represents a straight or branched chain alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more carbon atoms, -or phenyl optionally replaced by one to five R2 groups, which may be the same or different; R7 represents a straight or branched chain alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms, -phenyl optionally substituted by one to five R2 groups, which may be the same or different; or a halogen atom, - RB represents a hydrogen atom; a straight or branched chain alkyl, alkenyl or alkynyl group containing up to ten carbon atoms, which is optionally substituted by one or more halogen atoms, - a cycloalkyl group containing from three to six carbon atoms, - phenyl optionally substituted by from one to five groups, which may be the same or different, selected from halogen, nitro, cyano, R5, -S (0) pR5 and -OR5; or a group selected from -S02R6 and -OR5; R9 and R10, which may be the same or different, each represent a hydrogen atom, - a straight or branched chain alkyl group containing up to six carbon atoms, which is optionally substituted by one or more halogen atoms; or phenyl optionally substituted by from one to five R2 groups, which may be the same or different, - R "and R", which may be the same or different, each represents a hydrogen atom; or a straight or branched chain alkyl group containing up to 6 carbon atoms, which is substantially substituted by one or more halogen atoms; p represents zero, one or two, r represents zero, one or two; J? represents one, two or three, ü represents an integer from one to four; when t is greater than one, the groups -CR'R10- may be the same or different; or an agriculturally acceptable salt thereof, which possesses herbicidal properties.
3. 3. The herbicidal composition according to claim 1, wherein the component (a) is 2-cyano-1,3-dione of the formula wherein: (D R50 is a straight or branched chain alkyl group containing up to six carbon atoms, which is optionally substituted by one or more halogen atoms, which may be the same or different, or a cycloalkyl group containing from three to six carbon atoms, which is optionally substituted by one or more groups selected from R55 and one or more halogen atoms which may be the same or different, one of R51 and R'53 is -S (0) rR56 and the other of R51 and R53 is a halogen atom, a hydrogen atom, a straight or branched chain alkyl group containing up to six carbon atoms which is substituted by -OR55; -R55, -nitro, -cyano, - SR55; -OR55; -O (CH2) sOR55; O -C02R5S; R52 and R54, which may be the same or different, each is a halogen atom, - a hydrogen atom, a straight-chain alkyl group or branched that contains up to six carbon atoms which is replaced by -OR55; -R 55, -nitro, -cyano; -OR55; -0 (CH2) ßOR55; or -C02R55, -R55 and R56, which may be the same or different each is a straight or branched chain alkyl group containing up to six carbon atoms which may be optionally substituted by one or more halogen atoms, which they can be the same or different, - s is an integer from one to three, - r is zero, one or two; or an agically acceptable salt thereof.
4. 4. The herbicidal composition according to claim 1, wherein (b) is (i) a compound of the formula (Wherein D 70 is selected from the group consisting of haloalkyl, haloalkenyl, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, halogen, hydrogen, carboalkoxy, N-alkenylcarbamyalkyl, N-alkenyl carbamyl, N-alkyl-N-alkynylcarbamyl; alkyl-N-alquinilcarbamilalquil; N- carbamyl alkenyl alkoxyalkyl; N-alkyl -N-alquinilcarbamilalcoxialquil; alkynoxy; haloalkoxy tiocianatoalquil; alquenilaminoalquil; cyanoalkyl alquilcarboalquil; cianatoalquil; alkylthioalkyl alquenilaminosulfonalquil; alcoxicarboalquil haloalquilcarboniloxialquil; hidroxihaloalquiloxialquil haloalquenilcarbdniloxialquil; hydroxyalkyl hidroxialquilcarboalquiloxialqu.il; alcoxisulfonoalquil; furyl; thienyl alkyldiotylenyl; thienalkyl; substituted phenyl; wherein the substituents may be selected from halogen, alkyl, haloalkyl, alkoxy, carbamyl, nitro, carboxylic acids, and their salts, and haloalkylcarbamyl; phenylalkyl; phenylhaloalkyl; phenylalkenyl; substituted phenylalkenyl, wherein the substituents may be selected from halogen, alkyl, alkoxy, and halofenoxy, phenylalkoxy; phenylalkylcarboxyalkyl phenylcycloalkyl; halophenylalkenoxy; halothiophenylalkyl halofenoxyalkyl; bicycloalkyl; alkenylcarbamylpyridinyl alkynylcarbamylpyridinyl; dialkenylcarbamylbicycloalkenyl and alkynylcarbamylbicycloalkenyl, -R71 and R72, which may be the same or different, are selected from the group consisting of alkenyl; haloalkenyl; hydrogen; alkyl; haloalkyl; alkynyl; cyanoalkyl hydroxyalkyl; hydroxyhaloalkyl; haloalkylcarboxyalkyl alkylcarboxyalkyl; alkoxycarboxyalkyl thioalkylcarboxy alkyl, -alkoxycarboalkyl alkylcarbamyloxyalkyl, -amino; formyl; haloalkyl-N alkylamido; haloalkylamido; haloalkylamidoalkyl haloalkyl-N-alkylamidoalkyl; haloalkylamidoalkenyl alkylimido; cycloalkyl; alkylcycloalkyl; alkoxyalkyl alkylsulfonyloxyalkyl; mercaptoalkyl; alkylaminoalkyl alkoxycarboalkenyl; haloalkylcarbonyl; alkylcarbonyl alkenylcarbamyoxyalkyl, - cycloalkylcarbamyoxyalkyl alkoxycarbonyl; haloalkoxycarbonyl, -halophenylcarbamyoxyalkyl cycloalkenyl; phenyl; substituted phenyl wherein the substituents may be selected from alkyl, halogen, haloalkyl, alkoxy, haloalkylamido, phthalamido, hydroxy, alkylcarbamyloxy, alkenylcarbamyloxy, alkylamido, haloalkylamido and alkylcarboalkenyl; phenylsulfonyl; substituted phenylalkyl; wherein said substituents may be selected from halogen or alkyl; dioxyalkylene halophenoxyalkylamido alkyl; alkylthiodiazolyl; piperidyl piperidylalkyl; dioxolanialkyl, thiazolyl; alkylthiazolyl benzodiazolyl; halobenzothiazolyl; furious furil substituted with alkyl; furilalkyl; pyridyl; alkylpyridyl; alkoxazolyl; tetrahydrofuryl alkyl; 3-cyano-thienyl; thienyl substituted with alkyl; 4,5-polyalkylene thienyl; a-haloalkylacetamido-phenylalkyl; a-haloalkylacetamidonitrofenylalkyl; a-halo-alkylacetamidohalophenylalkyl and cyanoalkenyl; or R71 and R72 when taken together can form a structure consisting of piperidinyl; alkylpiperidinyl; pyridyl; di- or tetrahydropyridinyl; alkyltetrahydropyridyl; morpholyl; azabicyclononyl, - diasacicloalkanyl; benzoalkyl-pyrrolidinyl; oxazolidinyl, -perhydrooxazolidinyl-alkyloxazolidinyl; furiloxazolidinyl; thienyl oxazolidinyl pyridyloxazolidin .1; pyrimidinyloxazolidinyl benzooxazolidinyl; C3.7 alkylaminoalkenyl spironocycloalkyl-oxazolidinyl; alkylidenoimino, pyrrolidinyl piperidonyl; perhydroazepinyl, - perhydroazocinyl; pyrazolyl dihydropyrazolyl; piperazinyl; perhydro-1,4-diazepinyl quinolinyl; isoquinolinyl; dihydro-; tetrahydro-; or perhydroquinolyl or isoquinolyl; indolyl or di- or perhydroindolyl; and whose combined members R71 and R72, may be substituted with those independent radicals R71 and R72 listed above; or (ii) a compound selected from the group consisting of: α- (cyanomethoxy) imino] benzeneacetonitrile, - α- (1,3-dioxolan-2-ylmethoxy) imino] -benzeneacetonitrile; OximadeO- [3-dioxolan-2-ylmethyl] -2,2, 2-trifluoromethyl-4'-chloroacetophenone, -benzenemethanamine, N- [4- (dichloromethylene) -1, 3-diotolan-2-ylidene] -a- methyl, hydrochloride; methyl diphenylmethoxy acetic acid ester; 1,8-naphthalic anhydride, - cloquintoceto, - 4,6-dichloro-2-phenylpyrimidine, - 2-chloro-N- [1- (2,4,6-trimethylphenyl) ethenyl] acetamide; and ethylene glycol 1,1-dichloroacetone acetate.
5. The herbicidal composition according to claim 4, wherein component (b) is selected from the group consisting of 2,2,2-trimethyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5-phenyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5- (2-furanyl) -N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5- (2-thienyl) -N-dichloroacetyl oxazolidine; N, N-diallyl dichloroacetamide; 2, 2-spirocyclohexy-N-dichloroacetyl oxazolidine; 2,2-dimethyl-N-dichloroacetyl oxazolidine; 4- (dichloroacetyl) -3,4-dihydro-3-methyl-2H-1,4-benzoxazine, 3- [3- (dichloroacetyl) -2,2-dimethyl-5-oxalidinyl] pyridine, -4- ( dichloroacetyl) -l-oxa-4-azapiro- (4,5) -decane; 2,2-dichloro-1- (1,2,3,4-tetrahydro-1-methyl-2-isoquinolyl) ethanone; cis / trans-1,4-bis (dichloroacetyl) -2,5-dimethylpiperazine, - N- (dichloroacetyl) - 1, 2, 3, 4 -tetrahydroquinaldin, -1,5-bis (dichloroacetyl) -1,5- diazacyclononane; 1- (dichloroacetyl) -1-azaspiro [4, 4] nonane; a- [(cyanomethoxy) imino] benzeneacetonitrile; O 1 - [(1,3-dioxolan-2-ylmethoxy) imino] benzeneacetonitrile; O- [1, 3-dioxolan-2-ylmethyl] -2, 2, 2-trif luoroethyl-4'-chloroacetophenone, -benzenomet amine, N- [4- (dichloromethylene) -1, 3-diotolan 2-ylidene] -a-methyl; hydrochloride, - diphenylmethoxy acetic acid methyl ester; 1, 8-naphthalic anhydride, 4,6-dichloro-2-phenylpyrimidine; 2-Chloro-N- [1- (2,4,6-trimethylphenyl) ethenyl] -acetamide, - cloquintoceto, - and ethylene glycol acetal of 1,1-dichloroacetone.
6. The herbicidal composition according to claim 5, wherein component (b) is selected from the group consisting of 2,2,2-trimethyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5-phenyl-N-dichloroacetyl oxazoLidine; 2, 2-dimethyl-5- (2-furanyl) -N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5- (2-thienyl) -N-dichloroacetyl-dichloroacetamide oxazolidine of N, N-diallyl; 2, 2-spirocyclohexy-N-dichloroacetyl oxazolidine; 2,2-dimethyl-N-dichloroacetyl oxazolidine; and 4- (dichloroacetyl) -3,4-dihydro-3-methyl-2H-l, 4-benzoxazine.
7. The herbicidal composition according to claim 2, wherein component (a) is 4-benzoylsoxazole of the formula (I) in which R1 is a substituted or unsubstituted silopropyl group.
8. The herbicidal composition according to claim 7, wherein component (a) is selected from the group consisting of 5-cyclopropyl-4- [2-chloro-3-ethoxy-4- (ethylsulfonyl) benzoyl] isoxazole; 4- (4-chloro-2-methylsulfonylbenzoyl) -5-cyclopropylisoxazole; 5-cyclopropyl-4- (2-methylsulfonyl-4-trifluoromethylbenzoyl) -isoxazole; and 4- (4-bromo-2-methylsulfonylbenzoyl) -5-cyclopropylisoxazole; and agriculturally acceptable salts thereof.
9. The herbicidal composition according to claim 8, wherein the component (b) is selected from the group consisting of: 2,2,2-trimethyl-N-dichloroacetyl oxazolidine 2,2-dimethyl-5-phenyl oxazolidine -N-dichloroacetyl oxazolidine of 2,2-dimethyl-5- (2-furanyl) -N-dichloroacetyl oxazolidine of 2,2-dimethyl-5- (2-thienyl) -N-dichloroacetyl N, N-diallyl dichloroacetamide; 2,2-Spirocyclohexy-N-dichloroacetyl oxazolidine; 2,2-dimethyl-N-dichloroacetyl oxazolidine; and 4- (dichloroacetyl) -3,4-dihydro-3-methyl-2H-l, 4-benzoxazine.
10. 10. A method for reducing damage to crops by a 4-benzoylisoxazole or 2-cyano-1,3-dione herbicide, which comprises applying to the soil, crop or seed an antidotally effective amount of an effective antidote compound, which is effective antidote for said herbicide of 4-benzoylisoxazole or 2-cyano-1,3-dione.
11. The method according to claim 10, wherein said antidote compound is: (i) a compound of the formula OR C R71 '> R72 (D wherein R70 is selected from the group consisting of haloalkyl, haloalkenyl, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, halogen, hydrogen, carboalkoxy, N-alkenycarbamyalkyl, N-alkenylcarbamyl, N-alkyl-N-alkyl nylcarbamyl; alkyl-N-alkynylcarbamyl alkyl; N-alkenylcarbamyalkoxyalkyl; N-alkyl-N-alkynylcarbamyalkoxyalkyl; alkyloxy; haloalkoxy; thiocyanatoalkyl; • alkenylaminoalkyl; -alkylcarboalkyl; cyanoalkyl; cyanoalkyl; alkenylaminosulfonyl; alkylthioalkyl; haloalkylcarbonyloxyalkyl, -alkoxycarboalkyl haloalkenylcarbonyloxyalkyl; hydroxyhaloalkyloxyalkyl hydroxyalkyl carboalkyloxyalkyl, hydroxyalkyl alkoxysulfonoalkyl; furious thienyl; alkylthiolenyl; tienalkyl phenyl; substituted phenyl wherein the substituents may be selected from halogen, alkyl, haloalkyl, alkoxy, carbamyl, nitro, carboxylic acids and their salts, and haloalkylcarbamyl, -phenylalkyl; phenylhaloalkyl; phenylalkenyl; substituted phenylalkenyl wherein the substituents may be selected from halogen, alkyl, alkoxy, and halofenoxy, phenylalkoxy; phenylalkylcarboxyalkyl phenylcycloalkyl; halophenylalkenoxy, - halothiophenylalkyl halophenoxyalkyl; bicycloalkyl, - alkenylcarbamylpyridinyl alkynylcarbamylpyridinyl; dialkenylcarbamylbicycloalkenyl and alkynylcarbamylbicycloalkenyl; R71 and R72, which may be the same or different, are selected from the group consisting of alkenyl; haloalkenyl; hydrogen; alkyl; haloalkyl; alkynyl; cyanoalkyl hydroxyalkyl; hydroxyhaloalkyl; haloalkylcarboxyalkyl alkylcarboxyalkyl; alkoxycarboxyalkyl thioalkylcarboxyalkyl, alkoxycarboalkyl alkylcarbamyoxyalkyl; amino, - formyl; haloalkyl-N-alkylamido, -haloalkylamido; haloalkylamidoalkyl, -haloalkyl-N-alkylamidoalkyl; haloalkylamidoalkenyl; alkylimido; cycloalkyl; alkylcycloalkyl; alkoxyalkyl, alkylsulfonyloxyalkyl, mercaptoalkyl, alkylaminoalkyl, alkoxycarboalkenyl; haloalkylcarbonyl; alkylcarbonyl, alkenylcarbamyalloxyalkyl, cycloalkylcarbamyoxyalkyl alkoxycarbonyl; haloalkoxycarbonyl, -halophenylcarbamyoxyalkyl cycloalkenyl; phenyl; substituted phenyl wherein the substituents may be selected from alkyl, halogen, haloalkyl, alkoxy, haloalkylamido, phthalamido, hydroxy, alkylcarbamyloxy, alkenylcarbamyloxy, alkylamido, haloalkylamido and alkylcarboalkenyl; phenylsulfonyl; substituted phenylalkyl; wherein said substituents may be selected from halogen or alkyl; dioxyalkylene halophenoxyalkylamido alkyl; alkylthiodiazolyl; piperidyl piperidylalkyl; dioxolanialkyl, thiazolyl; alkylthiazolyl benzodiazolyl; halobenzothiazolyl; furious furil substituted with alkyl; furilalkyl; pyridyl; alkylpyridyl; alkoxazolyl; tetrahydrofuryl alkyl; 3-cyano-thienyl; thienyl substituted with alkyl; 4,5-polyalkylene thienyl; a-haloalkylacetamido-phenylalkyl; a-haloalkylacetamidonitrofenylalkyl; α-halo-alkylacetamidohalophenylalkyl and cyanoalkenyl, - or R71 and R72 when taken together can form a structure consisting of piperidinyl; alkylpiperidinyl; pyridyl; di- or tetrahydropyridinyl; alkyltetrahydropyridyl; morpholyl; azabicyclononyl; diazacycloalkanyl; benzoalkyl-pyrrolidinyl; oxazolidinyl, -perhydrooxazolidinyl, -alkyloxazolidinyl; furiloxazolidinyl; thienyl oxazolidinyl; pyridyloxazolidinyl; pyrimidinyloxazolidinyl, -benzooxazolidinyl; Spirocycloalkyl-oxazolidinyl C3.7; alkylaminoalkenyl, alkylideneimino; pyrrolidinyl; piperidonyl, - perhydroazepinyl; perhydroazocinyl, - pyrazolyl; dihydropyrazolyl; piperazinyl; perhydro-l, 4-diazepinyl; quinolinyl; isoquinolinyl; dihydro-; tetrahydro-, - or perhydroquinolyl or isoquinolyl; indolyl or di- or perhydroindolyl; and whose combined members R71 and R72, may be substituted with those independent radicals R71 and R72 listed above, - or (ii) a compound selected from the group consisting of: a- [(cyanomethoxy) imino] benzeneacetonitrile; a- [(1,3-dioxolan-2-ylmethoxy) imino] -benzeneacetonitrile; OximadeO- [3-dioxolan-2-ylmethyl] -2,2, 2-trifluoromethyl-4'-chloroacetophenone, -benzenemethanamine, N- [4- (dichloromethylene) -1, 3-diotolan-2-ylidene] -a- methyl, hydrochloride; methyl diphenylmethoxy acetic acid ester; 1, 8-naphthalic anhydride, - cloquintoceto, - 4,6-dichloro-2-phenylpyrimidine, - 2-chloro-N- [1- (2,4,6-trimethylphenyl) ethenyl] acetamide, - and ethylene glycol acetate 1, l-dichloroacetone.
12. The method according to claim 11, wherein said antidote compound is selected from the group consisting of 2,2,2-trimethyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5-f-enyl-N-dichloroacetyl oxazolidine, 2-dimethyl-5- (2-furanyl) -N-dichloroacetyl-oxazolidine, 2,2-dimethyl-2-yl oxazolidine (2 -thienyl) -N-dichloroacetyl; N, N-diallyl dichloroacetamide; 2, 2-spirocyclohexy-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-N-dichloroacetyl oxazolidine; 4- (dichloroacetyl) -3,4-dihydro-3-methyl-2H-l, 4-benzoxazine, -3- [3- (dichloroacetyl) -2,2-dimethyl-5-oxalidinyl] pyridine, -4- ( dichloroacetyl) -l-oxa-4-azapiro- (4,5) -decano, -2,2-dichloro-l- (1,2,3,4-tetrahydro-l-methyl-2-isoquinolyl) ethanone, - cis / trans-1, 4-bis (cycloacetyl) -2,5-dimethylpiperazine, - N- (dichloro-acetyl) -1, 2, 3,4-tetrahydroquinaldine, - 1-5-bis (dichloroacetyl) -1, 5-diazacyclononane; l- (dichloroacetyl) -1-azaspiro [4, 4] nonane; a- [(1,3-dioxolan-2-ylmethoxy) imino] benzeneacetonitrile; oxime O- [1, 3-dioxolan-2-ylmethyl] -2,2,2-trif luoromethyl-4'-chloroacetone, -benzenemethanamine, N- [4- (dichloro ethylene) -l, 3-diotolan-3, ilidene] -a-methyl; hydrochloride; methyl ester of acetic acid diphenylmethoxy; 1, 8-naphthalic anhydride; 4,6-dichloro-2-phenylpyrimidine, - 2-chloro-N- [1- (2,4,6-trimethylphenyl) ethenyl] -acetamide, - cloquintocet, and ethylene glycol acetal of 1,1-dichloroacetone.
13. 13. The method according to claim 12, wherein said antidote compound is selected from the group consisting of: 2,2,2-trimethyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5-phenyl-N-dichloroacetyl oxazolidine; oxazoli ina of 2, 2-dimethyl-5- (2-furanyl) -N-dichloroacetyl; 2, 2-dimethyl-5- (2-thienyl) -N-dichloroacetyl oxazolidine; N, N-diallyl dichloroacetamide; 2,2-Spirocyclohexy-N-dichloroacetyl oxazolidine, 2,2-dimethyl-N-dichloroacetyl-oxazolidine; and 4- (dichloroacetyl) -3,4-dihydro-3-methyl-2H-l, 4-benzoxazine.
14. The method according to claim 10, wherein the crop is corn.
15. 15. A method of reducing crop damage by a 4-benzoylisoxazole herbicide of the formula (I) wherein, R represents a hydrogen atom, a halogen atom, a straight or branched chain alkyl, alkenyl or alkynyl group containing more than six carbon atoms which is optionally substituted by one or more halogen atoms , - a cycloalkyl group containing from 3 to 6 carbon atoms optionally substituted by one or more groups -Rs, one or more halogen atoms or a C02R3 group, or a group selected from -CO-R3, -COR5 , cyano, nitro, or -CONR3R4; R1 represents a straight or branched chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms, - or a cycloalkyl group containing from three to six carbon atoms optionally substituted by one or more R5 groups or by one or more halogen atoms; R 2 represents a halogen atom, a straight or branched chain alkyl, alkenyl, alkynyl or alkoxy group containing up to 6 carbon atoms, which is optionally substituted by one or more groups -OR 5 or one or more halogen atoms; or a selected group of nitro, cyano, C02R3, -S (0) pR6, -0 (CH2) i77? R5, -COR5, -NR61r62, -N (R8) S02R7, -OR5, -OS02R7, -S02NR3R4, - CONR3R \ -CSNR3R4 and - (CR9R10) tS (O) qR7; n represents an integer from one to five; wherein n is greater than one, the R2 groups may be the same or different, - R3 and R4 each represents a hydrogen atom, a straight or branched chain alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms; R5 represents a straight or branched chain alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms, - a straight or branched chain alkenyl or alkynyl group containing from 3 to 6 carbon atoms; carbon, which is optionally substituted by one or more halogen atoms; or phenyl optionally substituted by one to five R2 groups which may be the same or different; Rs, R61 and R62, which may be the same or different, each represents a straight or branched chain alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more carbon atoms, or optionally phenyl replaced by one to five R2 groups, which may be the same or different; R7 represents a straight or branched chain alkyl group containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms, -phenyl optionally substituted by one to five R2 groups, which may be the same or different; or a halogen atom, - R8 represents a hydrogen atom, - a straight or branched chain alkyl, alkenyl or alkynyl group containing up to ten carbon atoms, which is optionally substituted by one or more halogen atoms; a cycloalkyl group containing from three to six carbon atoms, -phenyl optionally substituted by from one to five groups, which may be the same or different, selected from halogen, nitro, cyano, R5, -S (0) pR5 and - OR5; or a selected group of -S02Rs and -OR5; R9 and R10, which may be the same or different, each represent a hydrogen atom, - a straight or branched chain alkyl group containing up to six carbon atoms, which is optionally substituted by one or more halogen atoms; or phenyl optionally substituted by one to five R2 groups, which may be the same or different, - R51 and R52, which may be the same or different, each represents a hydrogen atom, - or a straight-chain alkyl group or branched containing up to 6 carbon atoms, which is optionally substituted by one or more halogen atoms, - p represents zero, one or two; g represents zero, one or two; m represents one, two or three; t represents an integer from one to four, - when t is greater than one, the groups -CR9R10- may be the same or different; or an agriculturally acceptable salt thereof, which possesses herbicidal properties; which comprises applying to the soil, crop or seed an antidotally effective non-phytoxoxic amount of an antidote compound which is antidotally effective for said 4-benzoylisoxazole herbicide.
16. 16. A method according to claim 15, wherein said antidote compound is: (i) a compound of the formula 0 II .71 R70"C" SN " (? D wherein R70 is selected from the group consisting of haloalkyl; haloalkenyl; alkyl; alkenyl; cycloalkyl, cycloalkylalkyl; halogen; hydrogen; carboalkoxy; N-alkenylcarbamyl-alkyl, -N-alkenyl carbamyl; N-alkyl-N-alkylnilcarbamyl; N-alkyl-N-alkynylcarbamyl alkyl; N-alkenylcarbamyl-alkoxyalkyl; N-alkyl-N-alkynylcarbamyl-alkoxyalkyl; alkynoxy; haloalkoxy thiocyanatoalkyl; acrylaminoalkyl; alkylcarboalkyl cyanoalkyl; cyanatoalkyl; alkenylaminosulfonyl-alkylthioalkyl; haloalk [uylcarbonyloxyalkyl; alkoxycarboalkyl haloalkenylcarbonyloxyalkyl; hydroxyhaloalkyloxyalkyl hydroxyalkylcarboalkyloxyalkyl; hydroxyalkyl alkoxysulfonoalkyl; furious thienyl; alkyldiothiolenyl thienalkyl; phenyl; substituted phenyl wherein the substituents may be selected from halogen, alkyl, haloalkyl, alkoxy, carbamyl, nitro, carboxylic acids and their salts, and haloalkylcarbamyl; phenylalkyl; f -ylhaloalkyl, -f-enylalkenyl; f-substituted allylkenyl wherein the substituents may be selected from halogen, alkyl, alkoxy, and halofenoxy, phenylalkoxy; phenylalkylcarboxyalkyl phenylcycloalkyl; halophenylalkenoxy, - halothiophenylalkyl halophenoxyalkyl; bicycloalkyl; alkenylcarbamylpyridinyl alkynylcarbamylpyridinyl, dialkenylcarbamylbicycloalkenyl and alkynylcarbamylbicycloalkenyl, R71 and R72, which may be the same or different, are selected from the group consisting of alkenyl; haloalkenyl; hydrogen; alkyl; haloalkyl; alkynyl; cyanoalkyl; hydroxyalkyl; hydroxyhaloalkyl; haloalkylcarboxyalkyl, -alkylcarboxyalkyl; alkoxycarboxyalkyl; thioalkylcarboxy-alkyl; alkoxycarboalkyl; alkylcarbamyoxyalkyl; amino formyl; haloalkyl-N-alkylamido, haloalkylamido haloalkylamidoalkyl, haloalkyl-N-alkylamidoalkyl haloalkylamidoalkenyl; alkylimido, -cycloalkyl alkylcycloalkyl; alkoxyalkyl; alkylsulfonyloxyalkyl mercaptoalkyl, -alkylaminoalkyl; alkoxycarboalkenyl haloalkylcarbonyl, -alkylcarbonyl, -alkenylcarbamyoxyalkyl cycloalkylcarbamyoxyalkyl; alkoxycarbonyl haloalkoxycarbonyl; halophenylcarbamyoxyalkyl; cycloalkenyl phenyl; substituted phenyl wherein the substituents may be selected from alkyl, halogen, haloalkyl, alkoxy, haloalkylamido, phthalamido, hydroxy, alkylcarbamyloxy, alkenylcarbamyloxy, alkylamido, haloalkylamido and alkylcarboalkenyl; phenylsulfonyl; substituted phenylalkyl; wherein said substituents may be selected from halogen or alkyl; dioxyalkylene, -halophenoxyalkylamido-alkyl; alkylthiodiazolyl; piperidyl; piperidylalkyl; dioxolanialkyl; thiazolyl; alkylthiazolyl; benzothiazolyl; halobenzothiazolyl, -furyl; furil substituted with alkyl; furilalkyl; pyridyl; alkylpyridyl; alkoxazolyl; tetrahydrofuryl alkyl; 3-cyano-thienyl; thienyl substituted with alkyl; thienyl 4,5-poly-alkylene, - a-haloalkylacetamidophenylalkyl; a-haloalkyl acetamidonitrofenylalkyl; a-halo-alkylacetamidohalophenyl-alkyl and cyanoalkenyl; or R71 and R72 when taken together can form a structure consisting of piperidinyl; alkylpiperidinyl; pyridyl; di- or tetrahydropyridinyl, - alkyltetrahydropyridyl; morpholyl; azabicyclononyl; diazacycloalkanyl; benzoalkyl-pyrrolidinyl; oxazolidinyl, -perhydrooxazolidinyl; alkyl oxazolidinyl, furoryloxazolidinyl; thienyl oxazolidinyl; pyridyloxazolidinyl, pyrimidinyloxazolidinyl; benzooxazolidi-nil; Spirocycloalkyl-oxazolidinyl C3-7; alkylaminoalkenyl, -alkylideneimino, -pyrrolidinyl; piperidonyl; perhydroazepinyl, -perhydroazocinyl; pyrazolyl; dihydropyrazolyl; piperazinyl; perhydro-l, 4-diazepinyl; quinolinyl; isoquinolinyl; dihydro-, tetrahydro-, or perhydro? ruinolyl or isoquinolyl; indolyl or di- or perhydroindolyl; and whose combined members R71 and R72, may be substituted with those independent radicals R71 and R72 listed above; or (ii) a compound selected from the group consisting of: a- [(cyanomethoxy) imino] benzeneacetonitrile; 01- [(1, 3-dioxolan-2-ylmethoxy) imino] -benzeneacetonitrile; OximadeO- [3-dioxolan-2-ylmethyl] -2, 2, 2-trifluoromethyl-4'-chloroacetophenone, -benzenome amine, N- [4- (dichloromethylene) -1, 3-diotolan-2-ylidene] -a -methyl, hydrochloride, - diphenylmethoxy acetic acid methyl ester; 1,8-naphthalic anhydride; cloquintoceto, 4,6-dichloro-2-phenylpyrimidine, 2-chloro-N- [1- (2,4,6-trimethylphenyl) ethenyl] acetamide, and ethylene glycol acetal of 1,1-dichloroacetone.
17. The method according to claim 16, wherein said antidote compound is selected from the group consisting of 2,2,2-trimethyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5-phenyl-N-dichlorocathyl oxazolidine; 2, 2-dimethyl-5-phenyl-N-dichloroacetyl oxazolidine; 2,2-dimethyl-5- (2-furanyl) -N-dichloroacetyl oxazolidine; 2,2-dimethyl-5- (2-thienyl) -N-dichloroacetyl oxazolidine; N, N-diallyl, 2,2-spirocyclohexy-N-dichloroacetyl dichloroacetamide; 2, 2-dimethyl-N-dichloroacetyl oxazolidine; 4- (dichloroacetyl) -3,4-dihydro-3-methyl-2H-l, 4-benzoxazine, -3- [3- (dichloroacetyl) -2,2-dimethyl-5-oxalidinyl] pyridine, -4- ( dichloroacetyl) -l-oxa-4-azapiro- (4,5) -decano, -2,2-dichloro-1- (1,2,3,4-tetrahydro-l-methyl-2-isoquinolyl) ethanone; cis / trans-1,4-bis (dichloroacetyl) -2,5-dimethyl-il-piperaz, -N- (dichloroacetyl) -1,2,3,4-tetrahydroquinaldin, -1,5-bis (dichloroacetyl) -1, 5-diazacyclononane, 1- (dichloroacetyl) -1-azaspiro [4, 4] nonane, -α- [(cyanomethoxy) imino] benzene acetonitrile; ar- [(1,3-dioxolan-2-ylmethoxy) imino] benzeneacetonitrile; oxime of 0- [1, 3-dioxolan-2-ylmethyl] -2, 2, 2-trifluoromethyl-4'-chloroacetophenone, -benzenomet amine, N- [4- (dichloromethylene) -1, 3-diotolan-2- ilidene] -a-methyl; hydrochloride, dif-enylmethoxy methyl ester of acetic acid; 1,8-naphthalic anhydride, - 4,6-dichloro-2-phenylpyrimidine, - 2-chloro-N- [1- (2,4,6-trimethylphenyl) ethenyl] -acetamide, - cloquintoke, - and acetal ethylene glycol 1,1-dichloroacetone.
18. 18. The method according to claim 17, wherein said antidote compound is selected from the group consisting of: 2,2,2-trimethyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5-f-enyl-N-dichloroacetyl-oxazolidine, 2,2-dimethyl-5- (2-furanyl) -N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5- (2-thienyl) -N-dichloroacetyl oxazolidine; N, N-diallyl dichloroacetamide; 2,2-Spirocyclohexy-N-dichloroacetyl oxazolidine, 2,2-dimethyl-N-dichloroacetyl-oxazolidine, - and 4- (dichloroacetyl) -3,4-dihydro-3-methyl-2H-l, 4-benzoxazine .
19. 19. The method according to claim 15, wherein the crop is corn. The method according to claim 15, wherein the 4-benzoylisoxazole herbicide of the formula (I) is selected from the group consisting of 5-cyclopropyl-4- [2-chloro-3-ethoxy-4] - (ethylsulfonyl) benzoyl] isoxazole; 4- (4-chloro-2-methylsulfonylbenzoyl) -5-cyclopropylisoxazole; 5-cyclopropyl-4- (2-methylsulfonyl-4-trifluoromethylbenzoyl) -isoxazole; and 4- (4-bromo-2-methylsulfonylbenzoyl) -5-cyclopropylisoxazole; and agriculturally acceptable salts thereof, and the antidote compound is selected from the group consisting of 2,2,5-trimethyl-N-trichloroacetyl oxazolidine; 2, 2-dimethyl-5-phenyl-N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5- (2-furanyl) -N-dichloroacetyl oxazolidine; 2, 2-dimethyl-5- (2-thienyl) -N-dichloroacetyl oxazolidine; N, N-diallyl dichloroacetamide; 2, 2-spirocyclohexy-N-dichloroacetyl oxazolidine; oxazolidine of 2,2-dimethyl-N-dichloroacetyl, - and 4- (dichloroacetyl) -3,4-dihydro-3-methyl-2H-l, 4-benzoxazine.