MXPA97003600A

MXPA97003600A - Herbicidal compositions sinergeti

Info

Publication number: MXPA97003600A
Application number: MXPA/A/1997/003600A
Authority: MX
Inventors: Ann Spangler Lori; Lidert Zev; Delbert Fisher James
Original assignee: Rohm And Haas Company
Priority date: 1996-05-23
Filing date: 1997-05-15
Publication date: 1998-07-03

Abstract

The present invention relates to compositions, having synergistic herbicidal effects, which comprise: (i) propanil, (ii) a compound of the formula: (wherein R 1 is alkyl, alkoxy, cycloalkyl, alkoxycarbonylalkyl) alkoxyalkyl, and R 2 and R 3 are , each independently alkyl, cycloalkyl, or together with the oxygen atoms to which they are bound form a 5-6 membered heterocyclic ring containing the phosphorus atom, X is an oxygen-sulfur atom, and Y is phenylophenyl substituted with up to three independently selected substituents of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy and haloalkoxy, or thienyloothienyl substituted with up to two substituents independently selected from halogen and alkyl, and (iii) an agronomically acceptable carrier, for the control of various grasses and herbs in rice . In particular, these compositions have synergistic properties to selectively control herbs in rice, especially grass of grasses, such as Barnyardgrass, Junglerice, Signalgrass and Sprangletop. The present invention also relates to a method for controlling herb species in rice comprising applying an effective herbicidal amount of (i) propanil, (ii) a compound of the formula (I), and (iii) an agronomically acceptable carrier. to the grass, the place of the grass, or the growth medium of the grass

Description

SYNERGISTIC HERBICIDES COMPOSITIONS The present invention relates to compositions with synergistic herbicidal effects. In particular, the present invention relates to the use of compositions comprising propanil, also known as N- (3,4-dichlorophenyl) propanamide, anilophos, also known as S- [N-chlorophenyl) -N-isopropylcarbamoylmethyl] -0 , 0-di ethyldithiophosphate, or other phosphate compounds structurally related to anilophos, and which is an agronomically acceptable vehicle as selective postemergence compositions for the control of various grasses and parasitic herbs in rice. In particular, these compositions have synergistic properties to selectively control herbs in rice, especially grass grasses, such as Barnyardgrass, Junglerice, Signalgrass and Sprangletop. These compositions are especially notable for Junglerice control, where some biotypes show resistance to conventional herbicide treatments. Typical compositions containing chemical herbal control agents allow for more efficient production by minimizing the growth of competing plants. New chemical means to control this undesirable vegetation are necessary to obtain a better control of several herbs of agronomic importance, for better crop safety and to overcome the resistance of the herbicides. Although many herbicides, including propanil and anilofos, are known individually as chemical control agents of grass for rice crops, their control is not sufficient at normal doses to effectively control certain grass grasses. The resulting competition of these herbs attenuates the production of rice in the plantations with its respective economic disadvantage. If the doses of propanil or anilofos are increased to the extent necessary to effectively control the herb species, the selectivity to the rice crop itself is decreased. This again attenuates rice production. Therefore there is a need for a more economical and selective method to control the herbal species in rice crops. It has been unexpectedly discovered that compositions comprising propanil and anilophos, and other phosphate compounds structurally related to the anilofos, result in greater control of grass species in rice, especially grass species, without increasing the dose and their respective problems of selectivity with rice. The herbicidal compositions can be applied to the rice crop, or to the place where the rice will be grown before the emergence of unwanted grass vegetation, or preferably after the emergence of unwanted herb vegetation. U.S. Patent No. 5,212,193 discloses synergistic microbial compositions of propanil and 2-alkyl-3-isothiazolones, but no herbicidal composition is suggested. Patents Nos. DE 42 41 629 and 42 09 475 disclose both synergistic herbicidal compositions of sulfonyl ureas and various other herbicides, including propanil and anilophos, but the composition of propanil and anilofos in the absence of sulfonyl urea do not It is suggested. The herbicidal compositions of the present invention comprise: (i) propanil; (ii) a compound of the formula: R1 O X I II II 3 Y - N - C - CH2 - S - P - OR3 (I) I 2 OR2 wherein: R1 is alkyl, alkoxy, cycloalkyl, alkoxycarbonylalkyl or alkoxyalkyl; R2 and R3 are each independently alkyl, cycloalkyl, or together with the oxygen atoms to which they are attached form a 5- or 6-membered heterocyclic ring containing the phosphorus atom; X is an oxygen or sulfur atom; and Y is phenyl or phenyl substituted with up to three substituents independently selected from halogen atoms, nitro, cyano, alkyl, haloalkyl, alkoxy and haloalkoxy; or is thienyl or thienyl substituted with up to two substituents independently selected from halogen and alkyl atoms; and (iii) an agronomically acceptable vehicle. As used to describe the present invention, the term "alkyl", whether alone or as part of another group, refers to a linear or branched alkyl chain. Examples of alkyl include (without limitation) methyl, ethyl, normal propyl, isopropyl, normal butyl, secondary butyl, isobutyl, tertiary butyl, normal pentyl, isopentyl, neopentyl, hexyl, isohexyl, secondary hexyl, 2,2-dimethylbutyl, and , 3-dimethylbutyl; and, as the following illustration, examples of alkoxy include methoxy, ethoxy, normal propoxy, isopropoxy, normal butoxy, secondary butoxy, isobutoxy, tertiary butoxy, isopentoxy, normal pentoxy, neopentoxy, hexyloxy, isohexyloxy, secondary hexyloxy, 2,2-dimethylbutoxy and 2, 3-dimethylbutoxy. "Cycloalkyl", whether alone or as part of another group, refers to a monocyclic and non-aromatic carboxylic ring. Examples of cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. "Haloalkyl" and haloalkoxy "refer to an alkyl and alkoxy group, respectively, substituted with one to five halogen atoms, preferably one to three halogen atoms, preferably fluorine or chlorine atoms. and haloalkoxy include, but are not limited to, trifluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy and trifluoromethoxy "Halo" includes fluorine, chlorine, bromine and iodine "Alkoxycarbonylalkyl" refers to an alkoxy group which is attached to a carbonyl group, which in turn is attached to an alkyl group Examples of alkoxycarbonylalkyl include, but are not limited to, methoxycarbonylmethyl, tertiary butoxycarbonylmethyl and 2- (methoxycarbonyl) ethyl. "Alkoxyalkyl" refers to to the alkoxy group which is attached to an alkyl group The examples of alkoxyalkyl include, but are not limited to, methoxymethyl, l-methoxy-2-propyl and 1- (normal butoxy) -2-propyl, In a preferred embodiment, the compositions h The herbicides of the present invention comprise a propanil and a compound of the formula (I), wherein: R1 is alkyl (of 1 to 4 carbon atoms), cycloalkyl (of 3 to 6 carbon atoms), alkoxy (of 1 to 4 carbon atoms), alkoxycarbonyl (of 1 to 4 carbon atoms) -alkyl or alkoxy ( from 1 to 4 carbon atoms) -alkyl (from 1 to 4 carbon atoms); R2 and R3 are each independently alkyl of (from 1 to 4 carbon atoms), cycloalkyl (from 3 to 6 carbon atoms), or together with the oxygen atoms to which they are attached form a heterocyclic ring of five to six members containing the phosphorus atom; X is an oxygen or sulfur atom; and Y is phenyl or phenyl substituted with up to three substituents independently selected from fluorine, chlorine, bromine, nitro, cyano, alkyl (from 1 to 4 carbon atoms), haloalkyl (from 1 to 4 carbon atoms), alkoxy (from 1 to 4 carbon atoms), and haloalkoxy (of 1 to 4 carbon atoms); or is thienyl or thienyl substituted with up to two substituents independently selected from fluorine, chlorine, bromine and alkyl (from 1 to 4 carbon atoms). In a more preferred embodiment, the herbicidal compositions of the present invention comprise propanil and a compound of the formula (I), wherein: R 1 is alkyl (2 to 4 carbon atoms); R2 and R3 are each independently alkyl (of 1 to 3 carbon atoms), cycloalkyl (of 3 to 6 carbon atoms) or together with the oxygen atoms to which they are attached form a heterocyclic ring of five to six members which they contain the phosphorus atom; X is an oxygen or sulfur atom; and Y is phenyl, 3-methylphenyl, 4-methylphenyl, 2,6-diethylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl , 3-trifluoromethylphenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoro-4-methoxymethylphenyl, 3-bromophenyl, 3-chlorophenyl, 3-fluorophenyl, 3-trifluoromethoxyphenyl, 3-cyanophenyl, 4-cyanophenyl, 2- fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3, 5-difluorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,5-dichlorophenyl, 3,5-dichlorophenyl, 2,4- difluorophenyl, 3-chloro-2-fluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, 3-chloro-4,6-difluorophenyl, 3,4,5-trifluorophenyl, 2-thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl, or 2,5-dichloro-3-thienyl. In an even more preferred embodiment, the herbicidal compositions of the present invention comprise propanil and a compound of the formula (I), wherein R 1 is normal propyl or isopropyl; R2 and R3 are each independently methyl, ethyl, normal propyl or isopropyl; X is a sulfur atom; and Y is phenyl, 4-fluorophenyl, 4-chlorophenyl, 3-fluorophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3-chloro-4-fluorophenyl, 3-chlorophenyl, 2-thienyl or 5-chloro-3 -thienyl In an even more preferred embodiment, the herbicidal compositions of the present invention comprise propanil and a compound of Formula (I) wherein R 1 is isopropyl; R2 and R3 are each independently methyl, ethyl, normal propyl or isopropyl; and Y is 4-fluorophenyl or 4-chlorophenyl. The most preferred herbicidal composition comprises propanil and anilophos, which is a compound of the formula (I), wherein R 1 is isopropyl, R 2 and R 3 are each methyl, X is a sulfur atom and Y is 4-chlorophenyl. A second embodiment of the present invention relates to a method for controlling herb species in rice comprising applying an effective herbicidal amount of a composition comprising (i) propanil, (ii) a compound of the formula (I) and (iii) ) an agronomically acceptable vehicle for the grass, the place of the grass or the growth medium of the grass. The relative proportion of the amount of propanil for a compound of the formula (I) which is used to increase the control of herbs in rice varies from 64 to about 4 parts by the weight of propanil, to about a part of the weight of a compound of the formula (I). Preferably, the ratio is 32 parts by weight of propanil to about one part by weight of a compound of the formula (I). Preferably, the ratio is between 16 parts by weight of propanil to about one part by weight of a compound of the formula (I). The compositions of the present invention are useful for both preemergence and postemergence applications, particularly in postemergence applications. The preemergence compositions are generally applied to the soil before, during or after sowing, but before the harvest arises. Post-emergence herbicides are applied after the plants emerge and during their growth period. The composition modalities show selectivity to rice, while they have a good control of Barnyardgrass, Junglerice, Signalgrass and Sprangletop. Under certain conditions, the compositions of the invention can be incorporated into the soil or to another growth medium before planting a crop. This incorporation can be by any convenient means, including mixing with the soil, applying the surface compound of the soil and then dragging it towards the ground and to the desired depth, or when using a liquid vehicle. The compositions of the present invention can be applied to various places, such as soil or foliage. The compositions are generally taken in a vehicle, or formulated to make them suitable for subsequent dissemination as a herbicidal composition. For example, these chemical agents can be formulated as wettable powders, emulsifiable concentrates, powders, granulated formations, aerosols or flow emulsion concentrates. In these formulations, the compositions are extended with a solid liquid carrier and, where desired, suitable surfactants are incorporated. It is generally desirable, particularly in the foliage spray formulas, to include adjuvants, such as wetting agents, spreading agents, dispersing agents, glues, adhesives and the like in accordance with agricultural practices. These adjuvants commonly used in the art can be allied in the publication of the John. McCutcheon, Inc. "Detergents and Emulsifieres, Annual." Allured Publishing Company, Ridgewood, New Jersey, E.U.A. The compositions of the present invention can be applied as herbicidal sprays by methods in the common course, such as conventional high-gallonage hydraulic sprays, low gallonage sprays, air-stream sprays, aerial sprays and powders. The dilution and application rate will depend on the type of equipment used, the method of application and the herbs to be controlled, but the preferred effective amount is about 1.2 kilograms per hectare of the active ingredient propanil and from 0.3 kilograms per hectare to about 0.02 kilogram. per hectare of the active ingredient of the formula (I). The compositions of the present invention can also be mixed with fertilizers or fertilizer materials before their application. In a type of solid fertilizer composition in which the composition of the invention can be used, fertilizer particles or fertilizer ingredients, such as ammonium sulfate, ammonium nitrate, or ammonium sulfate, can be coated with a compositions of the present invention. Solid compounds and solid fertilizer material can also be mixed in equipment in a mixer, or they can be incorporated with fertilizers in granular formulas. Any relative proportion of the fertilizer that is suitable for the crops and herbs that want to be treated can be used. These compositions provide fertilizer materials that promote the rapid growth of the desired plants, and at the same time control the growth of undesirable plants. The herbicidal activity of the compositions of the present invention towards a quantity of common herbs was evaluated using a greenhouse test method. Using the greenhouse test methods described below, propanil, anilophos and compositions of the present invention comprising propanil and anilofos were evaluated to control rice grasses selected from the following: Common Name Code Scientific Name Barnyardgrass (BYG) Echinochloa crus-galli Junglerice (JUN) Echinochloa colonum Signalgrass ( SIG) Brachiaria platyphylla Sprangletop (SPR) Leptochloa dubia The seeds of selected plants were planted in pots or lots. For preemergence tests, immediately after planting, the test compound was sprayed directly onto the soil surface. The lots or pots were placed in the greenhouse and then watered. For postemergence tests, the seeds were allowed to germinate and grow for 10 to 21 days. Before application, each series of test plants were selected for uniformity, size and stage of development. The test plants were then treated with the test compound, returned to the greenhouse and watered. The compound or composition to be evaluated was dissolved in a suitable solvent, usually acetone, and sprayed on the batches or pots using a vehicle volume equivalent to 234 or 268 liters per hectare at a rate of application of grams per hectare (g / Ha) specified in Table I. Approximately two or three weeks after the application of the test compound, the growth stage of the plant was observed. Each species was evaluated on a scale of 0 to 100, where 0 equals no activity, and 100 equals total control.

TABLE 1 - GREENHOUSE POST-EMERGENCY DATA It should be understood that various changes and variations may be made without departing from the spirit and scope of the present invention, as defined in the appended claims.

Claims

1. A herbicidal composition comprising; (i) propanil; (ii) a compound of the formula: wherein: R1 is alkyl, alkoxy, cycloalkyl, alkoxycarbonylalkyl or alkoxyalkyl; R2 and R3 are each independently alkyl, cycloalkyl, or together with the oxygen atoms to which they are attached form a 5- or 6-membered heterocyclic ring containing the phosphorus atom; X is an oxygen or sulfur atom; and Y is phenyl or phenyl substituted with up to three substituents independently selected from halogen atoms, nitro, cyano, alkyl, haloalkyl, alkoxy and haloalkoxy; or is thienyl or thienyl substituted with up to two substituents independently selected from halogen and alkyl atoms; and (iii) an agronomically acceptable vehicle.

2. The herbicidal composition of the claim 1, which comprises propanil and a compound of the formula (I) wherein: R 1 is alkyl (from 1 to 4 carbon atoms), cycloalkyl (from 3 to 6 carbon atoms), alkoxy (from 1 to 4 carbon atoms) ), alkoxycarbonyl (of 1 to 4 carbon atoms) -alkyl or alkoxy (of 1 to 4 carbon atoms) -alkyl (of 1 to 4 carbon atoms); R2 and R3 are each independently alkyl of (of 1 to 4 carbon atoms), cycloalkyl (of 3 to 6 carbon atoms), or together with the oxygen atoms to which they are attached form a heterocyclic ring of five to six members containing the phosphorus atom; X is an oxygen or sulfur atom; and Y is phenyl or phenyl substituted with up to three substituents independently selected from fluorine, chlorine, bromine, nitro, cyano, alkyl (from 1 to 4 carbon atoms), haloalkyl (from 1 to 4 carbon atoms), alkoxy (from 1 to 4 carbon atoms), and haloalkoxy (of 1 to 4 carbon atoms); or is thienyl or thienyl substituted with up to two substituents independently selected from fluorine, chlorine, bromine and alkyl (from 1 to 4 carbon atoms).

3. The herbicidal composition of the claim 2, which comprises propanil and a compound of the formula (I) wherein R 1 is alkyl (2 to 4 carbon atoms); R2 and R3 are each independently alkyl (from 1 to 3 carbon atoms), cycloalkyl (from 3 to 6 carbon atoms) or together with the oxygen atoms to which they are attached form a heterocyclic ring of five to six members containing the phosphorus atom; X is an oxygen or sulfur atom; and Y is phenyl, 3-methylphenyl, 4-methylphenyl, 2,6-diethylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl , 3-trifluoromethylphenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoro-4-methoxymethylphenyl, 3-bromophenyl, 3-chlorophenyl, 3-fluorophenyl, 3-trifluoromethoxyphenyl, 3-cyanophenyl, 4-cyanophenyl, 2- fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3, 5-difluorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,5-dichlorophenyl, 3,5-dichlorophenyl, 2,4- difluorophenyl, 3-chloro-2-fluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, 3-chloro-4,6-difluorophenyl, 3, 4,5-trifluorophenyl, 2-thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl, or 2,5-dichloro-3-thienyl. .

The herbicidal composition of claim 3, comprising propanil and a compound of the formula (I), wherein R 1 is normal propyl or isopropyl; R2 and R3 are each independently methyl, ethyl, normal propyl or isopropyl; X is a sulfur atom; and Y is phenyl, 4-fluorophenyl, 4-chlorophenyl, 3-fluorophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3-chloro-4-fluorophenyl, 3-chlorophenyl, 2-thienyl or 5-chloro-3 -thienyl

5. The herbicidal composition of the claim 4, which comprises propanil and a compound of the formula (I) wherein R 1 is isopropyl; R2 and R3 are each independently methyl, ethyl, normal propyl or isopropyl; and Y is 4-fluorophenyl or 4-chlorophenyl.

6. The herbicidal composition of the claim 5, which comprises propanil and anilophos.

7. A method for controlling herb species in rice comprising applying an effectively herbicidal amount of a composition comprising: (i) propanil; (ii) a compound of the formula: wherein: R 1 is alkyl, alkoxy, cycloalkyl, alkoxycarbonylalkyl or alkoxyalkyl; R2 and R3 are each independently alkyl, cycloalkyl, or together with the oxygen atoms to which they are attached form a 5- or 6-membered heterocyclic ring containing the phosphorus atom; X is an oxygen or sulfur atom; and Y is phenyl or phenyl substituted with up to three substituents independently selected from halogen atoms, nitro, cyano, alkyl, haloalkyl, alkoxy and haloalkoxy; or is thienyl or thienyl substituted with up to two substituents independently selected from halogen and alkyl atoms; and (iii) an agronomically acceptable vehicle for the grass, the grass site, or the growth medium of the grass.

The method of claim 11 for controlling herb species in rice, where the controlled herbs are Barnyardgrass, Junglerice, Signalgraas and Sprangletop.

9. The method of claim 8, wherein the herbs controlled with Barnyardgrass and Junglerice. The method of claim 7, wherein the relative ratio of the amount of propanil to the compound of the formula (I) ranges from 64 to about 4 parts by the weight of propanil of one part by the weight of a compound of the formula (I). The method of claim 10, wherein the ratio is between 32 parts by the weight of propanil to about one part by weight of a compound of the formula (I). The method of claim 10, wherein the ratio is between 16 parts by weight of propanil to about one part by weight of a compound of the formula (I). The method of claim 7, wherein the compound of the formula (I) is anilophos. SUMMARY The present invention relates to compositions, with synergistic herbicidal effects, comprising: (i) propanil; (ii) a compound of the formula: R1 0 X wherein: R1 is alkyl, alkoxy, cycloalkyl, alkoxycarbonylalkyl or alkoxyalkyl; R2 and R3 are each independently alkyl, cycloalkyl, or together with the oxygen atoms to which they are attached form a 5- or 6-membered heterocyclic ring containing the phosphorus atom; X is an oxygen or sulfur atom; and Y is phenyl or substituted phenyl - with up to three substituents independently selected from halogen atoms, nitro, cyano, alkyl, haloalkyl, alkoxy and haloalkoxy; or is thienyl or thienyl substituted with up to two substituents independently selected from halogen and alkyl atoms; and (iii) an agronomically acceptable vehicle, for the control of various grasses and herbs in the rice. In particular, these compositions have synergistic properties for selectively controlling herbs in rice, especially grass from grasses, such as Barnyardgrass, Junglerice, Signalgrass and Sprangletop. The present invention also relates to a method for controlling herb species in rice comprising applying an effective herbicidal amount of (i) propanil, (ii) a compound of the formula (I), and (iii) an agronomically acceptable carrier. to the grass, to the place of the grass, or to the growth medium of the grass.