PatentDe  


Dokumentenidentifikation EP1258193 23.12.2004
EP-Veröffentlichungsnummer 0001258193
Titel Zusammensetzungen aus Tetrazolinone-Herbizide und Antidote dafür
Anmelder Syngenta Ltd., Guildford, Surrey, GB
Erfinder Dagarin, Derek, Richmond, US;
Shribbs, John M., Petalume, US
Vertreter derzeit kein Vertreter bestellt
DE-Aktenzeichen 69827680
Vertragsstaaten AT, BE, CH, DE, DK, ES, FI, FR, GB, GR, IE, IT, LI, LU, MC, NL, PT, SE
Sprache des Dokument EN
EP-Anmeldetag 19.06.1998
EP-Aktenzeichen 020172581
EP-Offenlegungsdatum 20.11.2002
EP date of grant 17.11.2004
Veröffentlichungstag im Patentblatt 23.12.2004
IPC-Hauptklasse A01N 47/38

Beschreibung[en]
FIELD OF THE INVENTION

This invention relates to herbicide compositions and methods of use and, more particularly, to certain herbicidal compositions comprising tetrazolinone compounds and antidotes therefor which are useful as herbicides.

BACKGROUND OF THE INVENTION

An herbicide is a compound which adversely controls or modifies plant growth, e.g., killing, retarding, defoliating, desiccating, regulating, stunting, tillering, stimulating, and dwarfing. The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits. "Plant growth" includes all phases of development from seed germination to natural or induced cessation of life.

Herbicides 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 crop yield and reduce harvesting costs.

The most popular methods of herbicide application include: preplant incorporation into the soil; in-furrow application to seeds and surrounding soil; pre-emergence surface treatment of seeded soil; post-emergence treatment of the plant and soil; and preplant seed treatment.

A manufacturer of an herbicide generally recommends a range of application rates and concentrations calculated to maximize weed control. The range of rates varies from approximately 0.005 to 10 pounds per acre (0.0056 to 56 kilograms per hectare [kg/ha]), and is usually in the range of from 0.05 to 5 pounds per acre (0.056 to 5.6 kg/ha). The term "herbicidally effective amount" describes an amount of an herbicide compound which adversely controls or modifies plant growth. The actual amount used depends upon several considerations, including particular weed susceptibility and overall cost limitations.

An important factor influencing 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, certain herbicidal compounds are phytotoxic to some weed species but not to others. To be effective, an herbicide must cause minimal damage (preferably no damage) to the beneficial crop while maximizing damage to weed species which infest the locus of the crop.

To preserve the beneficial aspects of herbicide use and to minimize crop damage, many herbicide antidotes have been prepared. These antidotes reduce or eliminate damage to the crop without substantially impairing the damaging effect of the herbicide on weed species. See, for example, U.S. Patents Nos. 4,021,224, 4,021,229 and 4,230,874.

Identification of an antidote which safens an herbicide in crops is a highly complicated task. The precise mechanism by which an antidote reduces herbicidal crop injury has not been established. An antidote compound may be a remedy, interferent, protectant, or antagonist. As used herein, "antidote" describes a compound which has the effect of establishing herbicide selectivity, i.e., continued herbicidal phytotoxicity to weed species by the herbicide, and reduced or non-phytotoxicity to the cultivated crop species. The term "antidotally effective amount" describes an amount of an antidote compound which counteracts to some degree a phytotoxic response of a beneficial crop to an herbicide.

Tetrazolinone compounds have been found to be very effective herbicides with broad general herbicidal activity against broad-leafed and grass weeds by pre- and/or post-emergence application. The method of controlling vegetation with these compounds comprises applying an herbicidally effective amount of the compounds, usually with an inert carrier or diluent, to the area where herbicidal control is desired. However, the herbicidal tetrazolinone compounds have been found in some instances to adversely affect or interfere with the cultivation of crop plants, especially corn and soya crops. Therefore, the effective use of these herbicides for controlling weeds in the presence of such crops is further enhanced by, or may require in many instances, the addition of an antidotally effective amount of a compound, which is antidotally effective with the herbicide.

It has now been discovered that certain compounds when used in an antidotally effective amount are effective antidotes for the protection of crops, especially corn, wheat, rice and soya, from adverse herbicidal injury or the reduction of adverse herbicidal injury caused by the use of an herbicidally effective amount of a tetrazolinone compound. Therefore, it is an object of the present invention to provide compositions of tetrazolinone herbicides in combination with antidotes therefor, which compositions are useful to reduce injury to crops, especially corn, wheat, rice and soya, due to phytotoxicity of these herbicides.

SUMMARY OF THE INVENTION

The present invention relates to herbicidal compositions comprising herbicidal tetrazolinone compounds and antidotal compounds therefor to reduce injury to various crops, particularly corn, wheat, rice and soya, from the phytotoxic effects of such tetrazolinone herbicides when used alone or in combination with other compounds as co-herbicides.

More particularly, the invention relates to a composition comprising:

  • (a) an herbicidal tetrazolinone, or an agriculturally acceptable salt thereof;
  • (b) an antidotally effective amount of an antidote compound which is antidotally effective for said tetrazolinone, wherein the antidote compound is a substituted phenylpyrimidine.

The invention further relates to methods for reducing phytotoxicity or injury to crop plants, particularly corn, wheat, rice and soya crops, due to an herbicidal tetrazolinone compound, or salt thereof, by applying an antidotally effective amount of an antidote compound to the soil, crop or crop seed.

DETAILED DESCRIPTION OF THE INVENTION

Tetrazolinone herbicide compounds useful in the present invention are described in U.S. Patent Nos. 4,618,365; 4,826,529; 4,830,661; 4,956,469; 5,003,075; 5,019,152; 5,342,954; 5,344,814; 5,347,009; 5,347,010; 5,362,704 and 5,466,660 and in European Patent Publication No. 0 672 663 A1; 0 692 482 A2; 0 695 748 A1; 0 708 097 A1 and 0 711 761 A1. Herbicidal tetrazolinone compounds for use in this invention may 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 tetrazolinone compounds useful in this invention fall within the general formula

wherein:
  • R is hydrogen, optionally substituted C1-C12 alkyl, optionally substituted C2-C13 alkoxyalkyl, optionally substituted C1-C12haloalkyl, optionally substituted C7-C9 aralkyl, optionally substituted C5-C6 cycloalkyl, optionally substituted C3-C12 alkenyl, optionally substituted aryl, or optionally substituted heteroaryl;
  • Z is hydrogen, C1-C5 alkylcarbonyl, C2-C5 alkoxycarbonyl, S(O)n optionally substituted phenyl or C(O)NR1R2 wherein R1 and R2 are the same or different and are selected from the group consisting of: hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C3-C6 alkenyl, optionally substituted C5-C6 cycloalkyl and optionally substituted C7-C9 aralkyl; n is 0, 1 or 2; or
  • R1 and R2 together with the nitrogen to which they are attached form an optionally substituted saturated or unsaturated 5 or 6 membered heterocyclic ring wherein the ring members are selected from nitrogen, carbon, oxygen and sulfur; or an agriculturally acceptable salt thereof which possesses herbicidal properties.

Compounds of formula I(a) are among the more preferred class of compounds

   wherein R1 and R2 are either the same or different and are selected from the group consisting of hydrogen, optionally substituted C1-C12 alkyl, optionally substituted C3-C6 alkenyl, optionally substituted C2-C13 alkoxyalkyl, optionally substituted C1-C12 haloalkyl and optionally substituted C5-C6 cycloalkyl; and

   R3, R4, R5, R6 and R7 are either the same or different and are selected from the group consisting of hydrogen, halogen, optionally substituted C1-C12 alkyl, optionally substituted C2-C13 alkoxyalkyl, optionally substituted C1-C12 haloalkyl and optionally substituted C5-C6 cycloalkyl.

Preferred compounds are those in which R1 and R2 are the same or different and are selected from the group consisting of hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C1-C12 haloalkyl and C5-C6 cycloalkyl; and R3, R4, R5, R6 and R7 are selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, and C1-C12 haloalkyl.

Especially preferred compounds have the following formula I(b):

   wherein R3 is chloro or ethyl; R7 is hydrogen or chloro and R2 is ethyl or cyclohexyl; or an agriculturally acceptable salt thereof.

By the term "agriculturally acceptable salts" is meant salts the cations or anions of which are known and accepted in the art for the formation of salts for agricultural or horticultural use. Preferably the salts are water-soluble. Suitable acid addition salts, formed by compounds of formula (I) containing an amino group, include salts with inorganic acids, for example, hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids, for example, acetic acid. Suitable salts formed by compounds of formula (I) which are acidic, i.e., compounds containing one or more carboxy groups, with bases include alkali metal (e.g. sodium and potassium) salts, alkaline earth metal (e.g. calcium and magnesium) salts and ammonium and amine (e.g. diethanolamine, triethanolamine, octylamine, dioctylmethylamine and morpholine) salts.

As employed herein, the word "substituted " is intended to mean that the "substituted" group has one or more of the following substituents: halogen (i.e., fluorine, chlorine, bromine and iodine); C1-C4 alkyl; C1-C4 alkylthio; C1-C4 alkoxy; (C1-C4)alkoxy-(C1-C4)alkyl; (C1-C6)alkoxyCO-; C1-C4 alkyl-S(O)p-; nitro; nitrile; cyano; carboxy and salts, amides and esters thereof; alkanoyl of 2 to 4 carbon atoms; amino optionally substituted with one or two C1-C4 alkyl; phenyl optionally substituted with one or more C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)p-, nitro, halogen, fluorine, chlorine, bromine, cyano, or CF3 groups; a five or six membered heterocyclic ring containing one or more heteroatoms selected from O, N or S; a five or six membered heterocyclic ring containing one or more heteroatoms selected from O, N or S optionally substituted with one or more C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)p-, nitro, halogen, fluorine, chlorine, bromine, cyano, or CF3 groups; wherein p is 0, 1 or 2.

The term "optionally substituted aryl" is intended to include aryl groups, such as phenyl, naphthyl, benzyl and phenoxy which are unsubstituted or are substituted with one or more of the foregoing substituents. Similarly, the term "optionally substituted heteroaryl" is intended to include heteroaryl groups, such as pyridyl, pyrimidyl, triazinyl, thienyl, furyl and thiazolyl, which are unsubstituted or are substituted with one or more of the substituents listed above.

In the above definitions, the term "halogen" includes fluoro, chloro, bromo, and iodo groups. In polyhalogenated groups, the halogens may be the same or different.

This invention embodies a two-part herbicidal system comprised of (a) a tetrazolinone herbicide as described hereinabove and (b) an effective antidote therefor. It has been found that such antidote compounds can be selected from a wide range of chemical substances that have been found to be effective as herbicide antidotes for the above-described tetrazolinone herbicides. The preferred compositions of this invention may include any one or more of such antidotes with the herbicides. The variety of crops on which the above-described herbicides is useful can be significantly broadened by the use of an antidote to protect one or more crops from injury therefrom and render the composition more selective against weeds.

Preferably, the compositions of the present invention comprise an antidotally-effective amount of a compound selected from substituted phenylpyrimidines.

Substituted phenylpyrimidines are disclosed in U.S. Patent 4,493,726 and have the general formula

in which R41 is hydrogen or a number of substituents; n is an integer from 1 to 5; R42 and R44 are independently halogen or a number of substituents and R43 is hydrogen, halogen, C1-C6 alkyl, C1-C6 haloalkyl or phenyl. One member of this group is 4,6-dichloro-2-phenylpyrimidine (R41 - hydrogen, R42 and R44 = chlorine; R43 = hydrogen) also known as fenchlorim or CGA-123407.

Herbicidal compositions according to this invention may also contain one or more additional pesticidally active ingredients. Herbicides which may be used as co-herbicides with tetrazolinone compounds of formula (I) with benefit in combination with an antidote as described herein include, preferably, thiocarbamates (including dithiocarbamates), α-haloacetamides, heterocyclyl phenyl ethers, imidazolinones, pyridines and sulfonylureas. it is within the purview of this invention that other classes of herbicides, e.g., triazines, ureas, diphenyl ethers, nitroanilines, thiazoles, pyrrolidinones, aromatic and heterocyclic di- and triketones, etc., the individual members of which classes may be derivatives having one or more substituents selected from a wide variety of radicals may suitably be used a co-herbicides. Such combinations can be used to obtain selective weed control with low crop injury in several varieties of crop plants such as corn, grain sorghum, and cereals such as wheat, rice, barley, oats and rye, as well as several varieties of oil-seed crops such as soybeans and cotton. Insecticides, such as synthetic pyrethroids, fungicides, such as carbamates and triazoles and nematicides may also be included in the herbicidal compositions of this invention.

Effective weed control coupled with low crop injury is a result of treatment of a plant locus with a combination of an herbicidal tetrazolinone compound and an antidote compound in accordance with the present invention. By application to the "plant locus" is meant application to the plant growing medium, such as soil, as well as to the seeds, emerging seedlings, roots, stems, leaves, or other plant parts.

The phrase "combination of an herbicidal tetrazolinone compound and an antidote compound" includes various methods of treatment. For example, the soil of a plant locus may be treated with a "tank-mix" composition containing a mixture of the herbicide and the antidote which is "in combination." Or, the soil may be treated with the herbicide and antidote compounds separately so that the "combination" is made on, or in, the soil. After such treatments of the soil with a mixture of herbicide and antidote or by separate or sequential application of the herbicide and the antidote to the soil, the herbicide and antidote may be mixed into or incorporated into the soil either by mechanical mixing of the soil with implements or by "watering in" by rainfall or irrigation. The soil of a plant locus may also be treated with antidote by application of the antidote in a dispersible-concentrate form such as a granule. The granule may be applied to a furrow which is prepared for receipt of the crop seed and the herbicide may be applied to the plant locus either before or after in-furrow placement of the antidote-containing granule so that the herbicide and antidote form a "combination." Crop seed may be treated or coated with the antidote compound either while the crop seed is in-furrow just after seeding or, more commonly, the crop seed may be treated or coated with antidote prior to seeding into a furrow. The herbicide may be applied to the soil plant locus before or after seeding and a "combination" is made when both herbicide and an antidote-coated seed are in the soil. Also contemplated as a "combination" is a commercially-convenient association or presentation of herbicide and antidote. For example, the herbicide and antidote components in concentrated form may be contained in separate containers, but such containers may be presented for sale or sold together as a "combination." Or, the herbicide and antidote components in concentrated form may be in a mixture in a single container as a "combination." Either such a "combination" may be diluted or mixed with adjuvants suitable for soil applications. Another example of a commercially-presented combination is a container of antidote-coated crop seed sold, or presented for sale, along with a container of herbicide material. These containers may, or may not, be physically attached to each other, but nonetheless constitute a "combination of herbicide and antidote" when intended for use ultimately in the same plant locus.

In the foregoing description of various modes of application of the herbicide-antidote combinations, it is inherent that each form of application requires that in some manner, the herbicide and antidote will physically combine to form a "composition" of those agents.

The amount of a particular tetrazolinone herbicide to be applied to the plant locus or crop-growing area will vary with, inter alia, the nature of the weeds, the particular herbicide used, the time of application, the climate and the nature of the crop. Application rates of between about 0.01 kg/ha and 5.0 kg/ha of tetrazolinone herbicide are generally suitable, with a rate of about 0.1 kg/ha to 4.0 kg/ha being preferred, and about 0.1 kg/ha to 3.0 kg/ha being especially preferred.

The amount of a given antidote to be utilized in combination with the herbicide according to this invention and the manner of its utilization and resulting efficacy can vary according to various parameters, such as the particular antidote to be employed, the crop which is to be protected, the amount or rate of herbicide to be applied, and the soil and climatic conditions of the agricultural environment in which the combination is to be applied. The selection of a specific antidote for use in the herbicide composition, the manner in which it is to be applied (e.g., tank-mix, in-furrow application, seed treatment, etc.), the determination of activity which is non-phytotoxic but antidotally-effective, and the amount necessary to provide this result, can be readily performed utilizing the test procedures in the cited patents, such as U.S. Patent No. 4,021,224, in accordance with common practice in the art.

For other descriptions of antidotes and methods of their use, reference is made to U.S. Patent No. 3,959,304; U.S. Patent No. 3,989,503; U.S. Patent No. 3,131,509; U.S. Patent No. 3,564,768; U.S. Patent No. 4,137,070; U.S. Patent No. 4,294,764; U.S. Patent No. 4,256,481; U.S. Patent No. 4,415,353; and U.S. Patent No. 4,415,352.

The antidote is applied in combination with the herbicide in a non-phytotoxic antidotally effective amount. By "non-phytotoxic" is meant an amount of the antidote which causes at most minor or no injury to the desired crop species. By "antidotally-effective" is meant an antidote used in an amount which is effective as an antidote with the herbicide to decrease the extent of injury caused by the herbicide to the desired crop species.

The ratio of herbicide to antidote may vary depending upon the crop to be protected, weed to be inhibited, herbicide used, etc., but normally an herbicide-to-antidote ratio ranging from 1:25 to 60:1 parts by weight may be employed, although much higher rates of antidote may be used, e.g., 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 preferred weight ratio range is from about 1:1 to about 20:1, with an even more preferred weight ratio range being from about 2:1 to about 15:1.

In field applications, the herbicide, antidote, or a mixture thereof, may be applied to the plant locus without any adjuvants other than a solvent. Usually, the herbicide, antidote, or mixture thereof, is applied in conjunction with one or more adjuvants in liquid or solid form. Compositions or formulations containing mixtures of an appropriate herbicide and antidote usually are prepared by admixing the herbicide and antidote with one or more adjuvants such as diluents, solvents, extenders, carriers, conditioning agents, water, wetting agents, dispersing agents, or emulsifying agents, or any suitable combination of these adjuvants These mixtures can be in the form of particulate solids, granules, pellets, wettable powders, dusts, solutions, aqueous dispersions, or emulsions.

Application of the herbicide, antidote, or mixture thereof, can be carried out by conventional techniques utilizing, for example, hand-carried or tractor-mounted spreaders, power dusters, boom and hand sprayers, spray dusters, and granular applicators. If desired, application of the compositions of the invention to plants can be accomplished by incorporating the compositions in the soil or other media.

The following examples are for illustrative purposes only and are not intended as necessarily representative of the overall testing performed and are not intended to limit the invention in any way. As one skilled in the art is aware, in herbicidal testing, a significant number of factors that are not readily 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 amount of sunlight and water, soil type, pH of the soil, temperature, and humidity, among other factors. Also, the depth of planting, the application rate of the herbicide, the application rate of the antidote, and the ratio of the herbicide-to-antidote application, as well as the nature of crops being tested, can affect the results of the test. Results may vary from crop to crop within the crop varieties.

EXAMPLE I

The following example describes a post flooding post emergence herbicidal screening test. Seeds of one weed specie were seeded into small pots. The pots were previously filled with clay soil which contained 2.2% organic matter and had a pH of 5.7. The weed specie was Echinochloa crus-galli ("ECHCG") at two growth stages (2-leaf and 3-leaf). In addition, the rice hybrid "Kosihikara" (Oryza sativa) was also seeded and the testing done at the 3-leaf stage.

The pots were placed into plastic tubs, lined with a plastic bag. The rice pots were placed into the tubs with the weed specie. The tubs were flooded with water to a depth of 2-3 cm above the pots.

The water inside the tubs was injected with the following antidote compound 4,6-dichloro-2-phenyl-pyrimidine (safener 5) at a rate as indicated in Table 1. Next, the herbicide 1-(2-ethylphenyl)-4-(N,N-diethyl carbamoyl)-5(4H)-tetrazolinone (cmp 2) dissolved in acetone was injected at a rate of 0.063, 0.25, 0.50 and/or 1 kg per hectare. The degree of weed control was evaluated and recorded 27 days after treatment as a percentage of weed control as compared to the growth of the same species of the same age in an untreated control flat. Percent control is the total injury to the plants due to all factors including: inhibited emergence, stunting, malformation, albinism, chlorosis and other types of plant injury. The control ratings range from 0 to 100 percent, where 0 represents no effect with growth equal to the untreated control and where 100 represents complete kill. Representative results of the inventive compounds are shown in Table 1. TREATMENT % PLANT INJURY CMP 2

(g/ha)
Safener

(g/ha)
ECHCG 2 leaf ECHCG 3 leaf ORYSA
250 None 99 99 23 250 Safener 5

(500g/ha)
100 98 14

As may be seen from the above table, rice injury was reduced 9 % with the safener employed.

EXAMPLE II

The following example describes a post flooding, post emergence herbicidal screening test conducted similarly to Example I. The tubs were flooded 24 hours before application of the herbicides.

Herbicides used were compounds 1 [1-(2,6-dichlorophenyl)-4-(N,N-diethyl carbamoyl)-5(4H)-tetrazolinone], compound 2 [1-(2-ethylphenyl)-4-(N,N-diethyl carbamoyl)-5(4H)-tetrazolinone] and compound 3 [1-(2-chlorophenyl)-4-(N-ethyl,N-cyclohexyl carbamoyl)-5(4H)-tetrazolinone]. The safener used was safener 5 as in Example I.

Results are shown in Table 2. TREATMENT % PLANT INJURY Herbicide

(g/ha)
Safener (g/ha) ECHCG 2 leaf ECHCG 3 leaf ORYSA
CMP 1

250 g/ha
-- 100 100 73
CMP 1

250 g/ha
Safener 3,

(500 g/ha)
100 100 38
CMP 1

250 g/ha
Safener 5

(500g/ha)
100 100 45
CMP 2

63 g/ha
-- 100 98 22
CMP 2

63 g/ha
Safener 5

(500 g/ha)
100 93 17
CMP 3

2000 g/ha
-- 100 100 47
CMP 3

2000 g/ha
Safener 5

(500 g/ha)
100 100 48

As seen from the above data, the safener reduced injury to rice from these herbicides.


Anspruch[de]
  1. Herbizide Zusammensetzung, umfassend:
    • (a) eine herbizid wirksame Menge einer herbiziden Tetrazolinon-Verbindung der Formel
      worin:
      • R Wasserstoff, gegebenenfalls substituiertes C1-C12-Alkyl, gegebenenfalls substituiertes C2-C13-Alkoxyalkyl, gegebenenfalls substituiertes C1-C12-Halogenalkyl, gegebenenfalls substituiertes C7-C9-Aralkyl, gegebenenfalls substituiertes C5-C6-Cycloalkyl, gegebenenfalls substituiertes C3-C12-Alkenyl, gegebenenfalls substituiertes Aryl und gegebenenfalls substituiertes Heteroaryl darstellt,
      • Z Wasserstoff, C1-C5-Alkylcarbonyl, C2-C5-Alkoxycarbonyl, S(O)n-gegebenenfalls substituiertes Phenyl oder C(O)NR1R2, worin R1 und R2 die Gleichen oder verschieden sind und ausgewählt sind aus der
      • Gruppe, bestehend aus: Wasserstoff, gegebenenfalls substituiertem C1-C6-Alkyl, gegebenenfalls substituiertem C3-C6-Alkenyl, gegebenenfalls substituiertem C5-C6-Cycloalkyl und gegebenenfalls substituiertem C7-C9-Aralkyl, darstellt; n 0, 1 oder 2 ist; oder
      • R1 und R2 zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls substituierten gesättigten oder ungesättigten 5 oder 6 gliedrigen heterocyclischen Ring bilden, wobei die Ringglieder aus Stickstoff, Kohlenstoff, Sauerstoff und Schwefel ausgewählt sind;

        oder ein landwirtschaftlich verträgliches Salz davon, und
    • (b) eine als Antidot wirksame Menge einer Antidot-Verbindung, die für das Tetrazolinon als Antidot wirksam ist, wobei die Antidot-Verbindung ein substituiertes Phenylpyrimidin darstellt.
  2. Herbizide Zusammensetzung nach Anspruch 1, wobei Komponente (a) ein Tetrazolinon der Formel I(a)
    darstellt,

    worin R1 und R2 entweder die Gleichen oder verschieden sind und ausgewählt sind aus der Gruppe, bestehend aus Wasserstoff, gegebenenfalls substituiertem C1-C12-Alkyl, gegebenenfalls substituiertem C3-C6-Alkenyl, gegebenenfalls substituiertem C2-C13-Alkoxyalkyl, gegebenenfalls substituiertem C1-C12-Halogenalkyl und gegebenenfalls substituiertem C5-C6-Cycloalkyl; und

    R3, R4, R5, R6 und R7 entweder die Gleichen oder verschieden sind und ausgewählt sind aus der Gruppe, bestehend aus Wasserstoff, Halogen, gegebenenfalls substituiertem C1-C12-Alkyl, gegebenenfalls substituiertem C2-C13-Alkoxyalkyl, gegebenenfalls substituiertem C1-C12-Halogenalkyl und gegebenenfalls substituiertem C5-C6-Cycloalkyl.
  3. Herbizide Zusammensetzung nach Anspruch 1, wobei Komponente (a) ein Tetrazolinon der Formel I(b)
    darstellt,

    worin R3 Chlor oder Ethyl darstellt; R7 Wasserstoff oder Chlor darstellt und R2 Ethyl oder Cyclohexyl darstellt, oder ein landwirtschaftlich verträgliches Salz davon.
  4. Herbizide Zusammensetzung nach einem der Ansprüche 1 bis 3, wobei Komponente (b) 4,6-Dichlor-2-phenylpyrimidin darstellt.
  5. Verfahren zum Vermindern von Schädigung für Kulturen durch ein Tetrazolinon-Herbizid der Formel I, wie in Anspruch 1 definiert, das Applizieren einer nicht-phytotoxischen, als Antidot wirksamen Menge einer Antidot-Verbindung, die als Antidot für das Tetrazolinon-Herbizid wirksam ist, auf den Boden, die Kultur oder das Saatgut umfasst, wobei die Antidot-Verbindung ein substituiertes Phenylpyrimidin darstellt.
  6. Verfahren nach Anspruch 5, wobei das Antidot 4,6-Dichlor-2-phenylpyrimidin darstellt.
  7. Verfahren nach Anspruch 5 oder Anspruch 6, wobei die Kultur Mais, Weizen, Reis oder Soja ist.
  8. Verfahren nach einem der Ansprüche 5 bis 7, wobei das Tetrazolinon-Herbizid die Formel
    aufweist,

    worin:
    • R Wasserstoff, gegebenenfalls substituiertes C1-C12-Alkyl, gegebenenfalls substituiertes C2-C13-Alkoxyalkyl, gegebenenfalls substituiertes C1-C12-Halogenalkyl, gegebenenfalls substituiertes C7-C9-Aralkyl, gegebenenfalls substituiertes C5-C6-Cycloalkyl, gegebenenfalls substituiertes C3-C12-Alkenyl, gegebenenfalls substituiertes Aryl oder gegebenenfalls substituiertes Heteroaryl darstellt;
    • Z Wasserstoff, C1-C5-Alkylcarbonyl, C2-C5-Alkoxycarbonyl, S(O)n - gegebenenfalls substituiertes Phenyl oder C(O)NR1R2, worin R1 und R2 die Gleichen oder verschieden sind und ausgewählt sind aus der Gruppe, bestehend aus: Wasserstoff, gegebenenfalls substituiertem C1-C6-Alkyl, gegebenenfalls substituiertem C3-C6-Alkenyl, gegebenenfalls substituiertem C5-C6-Cycloalkyl und gegebenenfalls substituiertem C7-C9-Aralkyl, darstellt; n 0, 1 oder 2 ist; oder
    • R1 und R2 zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls substituierten gesättigten oder ungesättigten 5 oder 6 gliedrigen heterocyclischen Ring bilden, wobei die Ringglieder aus Stickstoff, Kohlenstoff, Sauerstoff und Schwefel ausgewählt sind;
    oder ein landwirtschaftlich verträgliches Salz davon.
Anspruch[en]
  1. An herbicidal composition comprising:
    • (a) an herbicidally effective amount of an herbicidal tetrazolinone compound of the formula
      wherein:
      • R is hydrogen, optionally substituted C1-C12 alkyl, optionally substituted C2-C13 alkoxyalkyl, optionally substituted C1-C12 haloalkyl, optionally substituted C7-C9 aralkyl, optionally substituted C5-C6 cycloalkyl, optionally substituted C3-C12 alkenyl, optionally substituted aryl, and optionally substituted heteroaryl,
      • Z is hydrogen, C1-C5 alkylcarbonyl, C2-C5 alkoxycarbonyl, S(O)n optionally substituted phenyl or C(O)NR1R2 wherein R1 and R2 are the same or different and are selected from the group consisting of: hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C3-C6 alkenyl, optionally substituted C5-C6 cycloalkyl and optionally substituted C7-C9 aralkyl; n is 0, 1 or 2; or
      • R1 and R2 together with the nitrogen to which they are attached form an optionally substituted saturated or unsaturated 5 or 6 membered heterocyclic ring wherein the ring members are selected from nitrogen, carbon, oxygen and sulfur; or an agriculturally acceptable salt thereof, and
    • (b) an antidotally effective amount of an antidote compound which is antidotally effective for said tetrazolinone, wherein the antidote compound is a substituted phenylpyrimidine.
  2. An herbicidal composition according to claim 1, wherein component (a) is a tetrazolinone of formula I(a)
       wherein R1 and R2 are either the same or different and are selected from the group consisting of hydrogen, optionally substituted C1-C12 alkyl, optionally substituted C3-C6 alkenyl, optionally substituted C2-C13 alkoxyalkyl, optionally substituted C1-C12 haloalkyl and optionally substituted C5-C6 cycloalkyl; and

       R3, R4, R5, R6 and R7 are either the same or different and are selected from the group consisting of hydrogen, halogen, optionally substituted C1-C12 alkyl, optionally substituted C2-C13 alkoxyalkyl, optionally substituted C1-C12 haloalkyl and optionally substituted C5-C6 cycloalkyl.
  3. An herbicidal composition according to claim 1, wherein component (a) is a tetrazolinone of formula I(b)
    wherein R3 is chloro or ethyl; R7 is hydrogen or chloro and R2 is ethyl or cyclohexyl; or an agriculturally acceptable salt thereof.
  4. An herbicidal composition according to any one of claims 1 to 3, wherein component (b) is 4,6-dichloro-2-phenylpyrimidine.
  5. A method of reducing injury to crops by a tetrazolinone herbicide of formula I as defined in claim 1, which comprises applying to the soil, crop or seed a non-phytotoxic antidotally effective amount of an antidote compound which is antidotally effective for said tetrazolinone herbicide, wherein said antidote compound is a substituted phenylpyrimidine.
  6. A method according to claims 5, wherein the antidote is 4,6-dichloro-2-phenylpyrimidine.
  7. A method according to claim 5 or claim 6, wherein the crop is corn, wheat, rice or soya.
  8. A method according to any one of claims 5 to 7, in which the tetrazolinone herbicide has the formula
    wherein:
    • R is hydrogen, optionally substituted C1-C12 alkyl, optionally substituted C2-C13 alkoxyalkyl, optionally substituted C1-C12 haloalkyl, optionally substituted C7-C9 aralkyl, optionally substituted C5-C6 cycloalkyl, optionally substituted C3-C12 alkenyl, optionally substituted aryl, or optionally substituted heteroaryl;
    • Z is hydrogen, C1-C5 alkylcarbonyl, C2-C5 alkoxycarbonyl, S(O)n optionally substituted phenyl or C(O)NR1R2 wherein R1 and R2 are the same or different and are selected from the group consisting of: hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C3-C6 alkenyl, optionally substituted C5-C6cycloalkyl and optionally substituted C7-C9 aralkyl; n is 0, 1 or 2; or
    • R1 and R2 together with the nitrogen to which they are attached form an optionally substituted saturated or unsaturated 5 or 6 membered heterocyclic ring wherein the ring members are selected from nitrogen, carbon oxygen and sulfur or an agriculturally acceptable salt thereof.
Anspruch[fr]
  1. Composition herbicide comprenant :
    • (a) une quantité efficace du point de vue herbicide d'un composé de tétrazolinone herbicide de formule
      où :
      • R est l'hydrogène, C1-C12-alkyle éventuellement substitué, C2-C13-alcoxyalkyle éventuellement substitué, C1-C12-halogénoalkyle éventuellement substitué, C7-C9-aralkyle éventuellement substitué, C5-C6-cycloalkyle éventuellement substitué, C3-C12-alcényle éventuellement substitué, aryle éventuellement substitué, et hétéroaryle éventuellement substitué,
      • Z est l'hydrogène, C1-C5-alkylcarbonyle, C2-C5-alcoxycarbonyle, phényle éventuellement substitué par S(O)n, ou C(O)NR1R2 où R1 et R2 sont identiques ou différents et sont choisis dans le groupe consistant en : l'hydrogène, C1-C6-alkyle éventuellement substitué, C3-C6-alcényle éventuellement substitué, C5-C6-cycloalkyle éventuellement substitué et C7-C9-aralkyle éventuellement substitué ; n est 0, 1 ou 2 ; ou
      • R1 et R2 forment avec l'azote auquel ils sont fixés un cycle hétérocyclique à 5 ou 6 chaînons saturé ou insaturé éventuellement substitué, où les chaînons du cycle sont choisis parmi l'azote, le carbone, l'oxygène et le soufre ;
         ou d'un sel acceptable du point de vue agricole de celui-ci, et
    • (b) une quantité efficace comme antidote d'un composé antidote qui est efficace comme antidote pour ladite tétrazolinone, où le composé antidote est une phénylpyrimidine substituée.
  2. Composition herbicide selon la revendication 1, où le composant (a) est une tétrazolinone de formule I(a)
    où R1 et R2 sont identiques ou différents et sont choisis dans le groupe consistant en l'hydrogène, C1-C12-alkyle éventuellement substitué, C3-C6-alcényle éventuellement substitué, C2-C13-alcoxyalkyle éventuellement substitué, C1-C12-halogénoalkyle éventuellement substitué et C5-C6-cycloalkyle éventuellement substitué ; et

       R3, R4, R5, R6 et R7 sont identiques ou différents et sont choisis dans le groupe consistant en l'hydrogène, un halogène, C1-C12-alkyle éventuellement substitué, C2-C13-alcoxyalkyle éventuellement substitué, C1-C12-halogénoalkyle éventuellement substitué et C5-C6-cycloalkyle éventuellement substitué.
  3. Composition herbicide selon la revendication 1, où le composant (a) est une tétrazolinone de formule I(b)
    où R3 est chloro ou éthyle ; R7 est l'hydrogène ou chloro et R2 est éthyle ou cyclohexyle ; ou un sel acceptable du point de vue agricole de celle-ci.
  4. Composition herbicide selon l'une quelconque des revendications 1 à 3, où le composant (b) est la 4,6-dichloro-2-phénylpyrimidine.
  5. Procédé de réduction des dégâts de cultures par un herbicide tétrazolinone de formule I selon la revendication 1 qui comprend l'application au sol, à la culture ou aux graines d'une quantité non phytotoxique, efficace à titre d'antidote, d'un composé antidote qui est efficace à titre d'antidote pour ledit herbicide tétrazolinone, où ledit composé antidote est une phénylpyrimidine substituée.
  6. Procédé selon la revendication 5, où l'antidote est la 4,6-dichloro-2-phénylpyrimidine.
  7. Procédé selon la revendication 5 ou la revendication 6, où la culture est le maïs, le blé, le riz ou le soja.
  8. Procédé selon l'une quelconque des revendications 5 à 7 dans lequel l'herbicide tétrazolinone a la formule
    où :
    • R est l'hydrogène, C1-C12-alkyle éventuellement substitué, C2-C13-alcoxyalkyle éventuellement substitué, C1-C12-halogénoalkyle éventuellement substitué, C7-C9-aralkyle éventuellement substitué, C5-C6-cycloalkyle éventuellement substitué, C3-C12-alcényle éventuellement substitué, aryle éventuellement substitué, ou hétéroaryle éventuellement substitué,
    • Z est l'hydrogène, C1-C5-alkylcarbonyle, C2-C5-alcoxycarbonyle, phényle éventuellement substitué par S(O)n, ou C(O)NR1R2 où R1 et R2 sont identiques ou différents et sont choisis dans le groupe consistant en : l'hydrogène, C1-C6-alkyle éventuellement substitué, C3-C6-alcényle éventuellement substitué, C5-C6-cycloalkyle éventuellement substitué et C7-C9-aralkyle éventuellement substitué ; n est 0, 1 ou 2 ; ou
    • R1 et R2 forment avec l'azote auquel ils sont fixés un cycle hétérocyclique à 5 ou 6 chaînons saturé ou insaturé éventuellement substitué, où les chaînons du cycle sont choisis parmi l'azote, le carbone, l'oxygène et le soufre ou sel acceptable du point de vue agricole de celui-ci.






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