HK1168252B - Safening penoxsulam herbicide injury in water-seeded, direct-seeded and transplanted paddy rice - Google Patents

Description

Safener for injury of penoxsulam herbicide in water-sown rice, direct-sown rice and transplanted rice

Technical Field

The present invention relates to safeners for herbicidal injury (herbicidal injury) caused by penoxsulam (2- (2, 2-difluoroethoxy) -N- (5, 8-dimethoxy [1, 2, 4] triazolo [1, 5-c ] pyrimidin-2-yl) -6- (trifluoromethyl) benzenesulfonamide) in water-seeded (water-seeded) rice, direct-seeded (direct-seeded) rice and transplanted (transplantad) rice.

Background

When pesticides such as plant protection agents and in particular herbicides are used, cultivated plants can be damaged to a certain extent, depending on various factors such as the dosage of the pesticide, the timing of the application of the pesticide relative to the crop stage, their method of application, the type of cultivated plant, the nature of the soil and the climatic conditions (e.g. duration of light, temperature and precipitation). Thus, it is known that cultivated plants to be protected from the adverse effects of undesired plant growth can be damaged to some extent when an effective dose of herbicide is used. Various substances capable of specifically preventing the adverse effect of herbicides on cultivated plants (i.e., protecting the cultivated plants while not significantly affecting the herbicidal effect on weeds to be removed) have been proposed to solve this problem. However, it has been found that the proposed antidotes often have only a narrow field of use, i.e. a particular antidote is often only suitable for use on individual species of cultivated plants and/or only protects the cultivated plants from individual herbicidal substances or substance classes.

U.S. patent 5,858,924 describes certain [1, 2, 4] triazolo [1, 5-c ] pyrimidin-2-yl) -arylbenzenesulfonamide compounds and their use as herbicides. While some of these compounds have proven to be particularly effective herbicides for controlling undesirable vegetation in water-seeded, direct-seeded and transplanted rice, they have also demonstrated a slight degree of damage to rice at concentrations required for proper control of undesirable vegetation.

Technical Field

It has now been surprisingly found that the phytotoxic effects of penoxsulam on rice can be mitigated by the use of clomazone, a rice herbicide that itself has a different mode of action. The present invention relates to a composition for protecting water-seeded, direct-seeded and transplanted paddy rice from the harmful effects of penoxsulam and its agriculturally acceptable salt derivatives, which composition comprises clomazone as a safener in addition to penoxsulam. The present invention relates to a method for protecting water-seeded, direct-seeded and transplanted paddy rice from the harmful effects of penoxsulam and its agriculturally acceptable salt derivatives, which comprises contacting the water-seeded, direct-seeded and transplanted paddy rice with clomazone as a safener or applying clomazone to the cultivation area as a safener.

Penoxsulam is the common name for 2- (2, 2-difluoroethoxy) -N- (5, 8-dimethoxy [1, 2, 4] triazolo [1, 5-c ] pyrimidin-2-yl) -6- (trifluoromethyl) benzenesulfonamide. Its herbicidal activity is described in The pesticide manual, fourtenth Edition, 2006. Penoxsulam controls annual weeds, broadleaf weeds and sedges in rice fields, but it exhibits some phytotoxicity to rice at certain application rates (rates), flooding (water flooding), application timing and under conditions of the rice variety.

Clomazone is the common name for 2- [ (2-chlorophenyl) methyl ] -4, 4-dimethyl-3-isoxazolidinone. Its herbicidal activity is described in The Pesticide Manual, fourtenth Edition, 2006. Clomazone controls a wide range of weeds in rice fields and certain broadleaf crops.

The term "herbicide" as used herein means an active ingredient that kills, controls, or adversely modifies the growth of undesired plants. An herbicidally effective or vegetation controlling amount is an amount of active ingredient that causes an adversely modifying effect, including deviations from natural development, killing, regulation, desiccation, retardation, and the like. The terms "plant" and "vegetation" include germinating seeds (germinant seed), unearthed seedlings (emeringseed) and established vegetation (estabilished vegetation). The term "safener" as used herein refers to one or more compounds that selectively protect crops from herbicide damage without significantly reducing activity against the target weed species.

The compounds exhibit herbicidal activity when applied directly to the plant or to the locus of the plant via foliar, soil or water application at any stage of growth or prior to planting or germination of the plant. The effect observed depends on the plant species to be controlled, the growth stage of the plant, the application parameters of dilution and spray droplet size, the particle size of the solid components, the environmental conditions at the time of use, the specific compounds employed, the specific adjuvants and carriers employed, the soil type, the paddy water quality and depth, etc., and the amount of chemicals employed. It is known in the art that these and other factors can be adjusted to promote non-selective or selective herbicidal action. It is generally preferred that the compositions of the present invention be applied to relatively immature undesirable vegetation to achieve maximum control of weeds.

Cultivated plants to be protected from the adverse effects of undesired plant growth can be damaged to some extent when an effective dose of herbicide is used. Safeners are understood to mean the prevention of the adverse effect of the herbicide on the cultivated plants, i.e. the protection of the cultivated plants while not significantly affecting the herbicidal action on the weeds to be removed.

In the compositions of the invention, the weight ratio of penoxsulam to clomazone is from 1:2 to 1:100, preferably in the range from 1:5 to 1:20, at which the herbicidal action on the cultivated plants is safe.

The proportion of the safety composition applied will depend on the particular weed type to be controlled, the degree of control desired, and the timing and method of application. Typically, the compositions of the present invention may be applied at application rates of from 5 to 60 grams per hectare (g/ha) of penoxsulam and from 100 to 650g/ha of penoxsulam, respectively, in the composition. In a particularly preferred embodiment of the invention, clomazone is applied at a rate of 220g/ha to 450g/ha and penoxsulam is applied at a rate of 40 g/ha.

Penoxsulam and clomazone for use in the present invention may be applied separately or together as components of a multi-component herbicide system.

The herbicide-safener mixtures of the present invention may be applied with one or more other herbicides to control a wider variety of undesirable vegetation. When used in combination with other herbicides, the composition can be formulated with the other herbicide or herbicides, mixed with the other herbicide or herbicides in a container, or applied sequentially with the other herbicide or herbicides. Some rice herbicides that may be used in combination with the present safety composition include 2, 4-D esters and amines, 2-methyl-4-chloro (MCPA), fenchloramide (acetochlor), acifluorfen (acifluorfen), aclonifen (acifluorfen), AE0172747, alachlor (alachlor), sulfosulfuron (amidosulfofuron), aminopyralid (amidopyric acid), aminotriazole (amidotriazole), ammonium thiocyanate (ammonium thiocyanate), anilifos, azimsulfuron (azosulfuron), benfursuluron (benfuresate), bensulfuron-methyl (bensuluron-methyl), bentazone (bentazone), fenpyrazone (fensulfuron-methyl), fenpyrazamide (fenflurazone), fenflurazone (fenflurazone), fenflurazone, Clopyralid (clopyralid), cloransulam-methyl, cyclosulfamuron (cycloproprione), cycloxydim (cycloxydim), cyhalofop-butyl (cyhalofop-butyl), dicamba (dicamba), dichlobenil (dichlobenil), 2, 4-dichlorprop-P (dichlorprop-P), flumetsulam (diclosulam), diflufenican (diflufenican), diflufenzopyr, dimethenamid (dimethenamid-P), diquat (diquat), dithiopyr (dithiopyr), diuron (diuron), EK2612, EPTC, dicamba (dimethenamid-P), flumetsulam (diquat), dithiopyr (dithiphonil) (dithiapyr), dicoforon (diuron), flumetm (pyrazosulfuron-751), fenoxate (pyrazosulfuron), fenoxate (pyraflufen-ethyl), fenoxate (pyraflufenoxate-P), fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P, fenoxaprop-, fluazifop-P-butyl, flupyrosulfuron (fluetosulfuron), flufenacet (flufenacet), flupyridazinyl-ethyl, flumetsulam (fluetsulam), fluoroeleaf (flurazon), flumeturon (fluometuron), flupyrsulfuron (flupyruron), fluroxypyr (fluoxypyr), fluroxypyr, flufenide (fluxafen), fomesafen (flufenuron), fluridone (flufenuron), glufosinate-ammonium (glufosinate-ammonium), glyphosate (glyxate), chlorimuron (pyrosulfuron), pyribenzoxim (halosulfuron), pyrimethanil (flufenuron), pyribenzoxim (halosulfuron), pyrimethanil (fluquinate), pyrimethanil (fluquinacr-201), pyrimethanil (fluquindox), pyrimethanil (fluquinacr-ammonium), pyrimethanil (fluquinacr-201), pyrimethanil (fluquinacr-P), pyrimethanil (fluquinacr-201), pyrimethanil (fluquindox (fluazuron), pyrimethanil (fluquindox), pyrimethanil (fluazuron (fluquindox), pyrim (fluquinacr), iman (fluquindox), imazamide (fluquindox), pyrimethanil (fluquindox), pyrim (iman (imazamide (ima), pyrimethanil (iman (imazametham), pyrim (imazametham), imazametham (ima), pyrimethanil (iman), pyrimethanil (imazametham), pyri, Iodosulfuron (iodosulfuron), ioxynil (ioxynil), IR 5790, isoproturon (isoprotrotron), isoxaben (isoxaben), isoxaflutole (isoxaflutole), KUH-021, lactofen (lactofen), linuron (linux), MCPA ester & amine, mezoprop-P (mecoprop-P), mefenacet (mefenacet), mesosulfuron (mesosulfuron), mesotrione (mesotrione), metamifop (metamifop), metosulam (metamifop), metribuzin (metribuzin), metsulfuron (metafuroron), molinate (molinate), MSMA (mesofenate), metolachlor (metosulam), metosulam (metosulam), metribuzin (metribuzin), metsulfuron (metsulfuron), metosulam (metosulam), metosulam (metosultrin), metosulam (metosulam), metosulam (ethoxyfen-ethyl (ethyl, metosulam), metosulam (ethoxyfen-ethyl), metosulam (metofen-ethyl, metosulam), metosulam (metosulam), metosulam (metosulam, metosulam (metosulam, metosulam (metosulam), metosulam (metosulam), picloram (picloram), picolinafen (picolinafen), pyrazophos (piprophos), pretilachlor (pretilachlor), clethodim (profoxdim), propafen (propachlor), propanil (propanchlorin), propanil (propanil), propyzamide (propzamide), prosulfocarb (prosulfocarb), prosulfonone (prosulfon), pyraclonil (pyraclonil), pyrazogyl (pyrazosulfuron), pyrithiobac-sodium (pyribenzoxim), pyrithiobac-sodium (pyriftalid), pyriminosulfluramid (KUHU-021), pyrithiodin (pyriminobac-methyl), primisulfuron (pyrithion), pyrithionuron (pyrithiobac-547), metoxuron (Kuh-021), pyrithiobac (pyriminobac-methyl), pyrithiobac (pyrithiobac-sodium), pyrithiobac (pyrithiobac-sodium (fenthiuron (S-sodium), pyribenzofenacetron (pyribenzofenacetone (pyrazofenoxate (S-ethyl), pyribenzofenacetone (pyribenzofenacet-2), pyribenzofenacetone (pyribenzofenacet), pyribenzofenacet-ethyl (pyribenzofenacet), pyribenzofenacetone (S-2, pyribenzofenacetone (pyribenzofenacet), pyribenzofenacetone (pyribenzofenacet-ethyl (propanil-, Tebuthiuron (tebuthiuron), tefuryltrione (AVH-301), fenthiuron (thiazopyr), thiobencarb (thiobencarb), triclopyr esters and amines and triflusulfuron (tritosulfuron).

It is generally preferred that the herbicide-safener mixtures of the invention are used in combination with herbicides which are selective for the crop treated and which complement the spectrum of weeds controlled by these compounds at the application rates used. It is also generally preferred that the safety compositions of the present invention and other complementary herbicides are applied simultaneously in a combined formulation or container mixture.

In practice, it is preferred to use the safety compositions of the present invention in a mixture containing a herbicidally effective amount of the herbicidal component and at least one agriculturally acceptable adjuvant or carrier. The carrier may be water, soil, sand, fertilizer particles, clay particles, paper/cellulose particles or other materials that may serve as physical carriers for the safety composition. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations used when applying the compositions for selective weed control in the presence of the crop and should not chemically react with the herbicidal component or other composition ingredients. These mixtures may be designed for direct application to the weeds or their locus, or may be concentrates or formulations which are usually diluted with other carriers and adjuvants prior to application. They may be solids such as sand, soil, dust, granules, water-dispersible granules or wettable powders or liquids such as emulsifiable concentrates (emulsifiableconcentrates), solutions, emulsions, suspensions or water.

Suitable agriculturally acceptable adjuvants and carriers that may be used in preparing the herbicidal mixtures of the present invention are well known to those skilled in the art.

Liquid carriers which may be employed include water, toluene, xylene, petroleum spirits (petroleum naphthas), crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, tetrachloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl and diethylene glycol monomethyl ethers, methanol, ethanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, glycerol, N-methylpyrrolidin-2-one, N-dimethylalkylamides, dimethyl sulfoxide, liquid fertilizers and the like. Water is generally the carrier of choice for dilution of the concentrate.

Suitable solid carriers include talc, pyrophyllite (pyrophyllite clay), silica, activated clay (attapulgus clay), kaolin, diatomaceous earth (kieselguhr), chalk (chalk), diatomaceous earth (diatomaceous earth), lime, calcium carbonate, bentonite, Fuller's earth, cotton seed hulls (cotton seed hull), wheat flour, soy flour, pumice (pumice), wood flour, walnut shell flour (walnut shell flours), lignin, and the like.

It is generally desirable to incorporate one or more surfactants into the compositions of the present invention. The surfactants are advantageously used in solid and liquid compositions, especially compositions designed to be diluted with a carrier prior to application. Surfactants can be anionic, cationic or nonionic in nature and can be used as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants which are commonly used in the formulation art and which may also be used in the formulations of the present application are described, inter alia, in "McCutcheon's detergents and Emulsifiers annular," MC Publishing Corp., Ridgewood, New Jersey, 1998 and "Encyclopedia of Surfactants," Vol.I-III, Chemical Publishing Co., New York, 198-. Typical surfactants include alkyl sulfates such as diethanol-ammonium lauryl sulfate; alkyl aryl sulfonates such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C16 ethoxylate; soaps, such as sodium stearate; alkyl naphthalene-sulfonates, such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates, such as sodium bis (2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl methyl-ammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of monoalkyl phosphates and salts of dialkyl phosphates; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils.

Other additives commonly used in agricultural compositions include compatibilizers (compatibility agents), defoamers, masking agents (sequencing agents), neutralizing agents and buffers, corrosion inhibitors (corrionising inhibitors), dyes, fragrances (odor), spreading agents (spraying agents), permeation aids, stickers, dispersants, thickeners, freezing point depressants, biocides, and the like. The compositions may also contain other compatible components such as other herbicides, plant growth regulators, fungicides, insecticides, and the like and may be formulated with liquid fertilizers or solid particulate fertilizer carriers such as ammonium nitrate, urea, and the like.

The concentration of active ingredient in the herbicide-safener mixtures according to the invention is generally from 0.001 to 98% by weight (percent by weight). Concentrations of 0.01 to 90 wt.% are generally used. In compositions designed to be used in the form of concentrates, the active ingredient is generally present in a concentration of from 5 to 98% by weight, preferably from 10 to 90% by weight. The compositions are typically diluted with an inert carrier (e.g., water) prior to administration. The diluted compositions usually applied to the weeds or to the locus of the weeds generally contain from 0.0001 to 1% by weight of active ingredient and preferably contain from 0.001 to 0.05% by weight of active ingredient.

The compositions of the present invention may be applied to the weeds or their locus by using conventional ground or aerial dusters, sprayers and granule applicators, manually applied to the weeds or their locus or by addition to paddy field or irrigation water and by other conventional means known to those skilled in the art.

Detailed Description

The following examples illustrate the invention.

Evaluation of post-emergence weeding safety of water-sown rice

Pre-germinated rice was applied directly to the paddy field which had been flooded. The paddy field is prepared according to conventional cultivation practices by applying a suitable fertilizer, leveling the land before flooding, and flooding the entire field with water to a depth of 1 to 5(2.54 to 12.7 cm) inches, followed by sowing pre-germinated rice seedlings.

The treatment agents include penoxsulam and clomazone, which are treatment agents formulated in granular form, applied alone and in combination directly to the rice-seeded fields. These treatment agents may also be applied as liquid application forms applied directly to the water. Clomazone was applied on the day of sowing rice, on day 13 after sowing rice, and a combination of clomazone and penoxsulam was applied on day 13 after sowing rice. Penoxsulam was applied alone and in combination with clomazone on day 13 after sowing the rice.

The Colby's equation was used to determine the expected herbicidal effect of the mixture (Colby, s.r. conservation of the synthetic and antibacterial responses of the herbicide combinations. weeds1967, 15, 20-22.).

The following equation was used to calculate the expected activity of a mixture containing two active ingredients, a and B:

expectation value of A + B- (A × B/100)

Observed efficacy of active ingredient a at the same concentration as used in the mixture

B ═ observed efficacy of active ingredient B at the same concentrations used in the mixtures

Some of the safener-herbicide combinations tested, the application rates and rates used, the plant species tested and the results are shown in tables 1-3.

Evaluation of herbicide safety in Water-seeded Rice

Tables 1 and 2 show that clomazone is safe active against rice damage caused by penoxsulam applied directly to water seeded rice. Table 1 shows that penoxsulam applied at 40gai/ha on day 13 after sowing of rice causes slight damage to rice on days 7, 14 and 21 after this application, with the% damage visually decreasing with time. Clomazone applied to water-seeded rice at the same time (day 13 after sowing) caused slight (0-3%) visual damage to the rice. When penoxsulam and clomazone are applied simultaneously on the 13 th day after sowing, the rice damage is remarkably reduced due to the safety effect of the clomazone on the damage of penoxsulam to the water-sowed rice. As the proportion of clomazone increases, its safety effect on injury to rice caused by penoxsulam also increases, as observed by the decrease in visual injury assessment.

Table 2 shows that clomazone also has a safety effect on injury caused by penoxsulam to rice seedlings (rice stand) or rice plant populations per unit area. Furthermore, as seen from the visual damage assessment% of table 1, clomazone has a safety effect on the effect of penoxsulam on rice seedlings. Penoxsulam had a slight negative effect on rice seedlings, and clomazone had negligible effect on rice seedlings. The rice seedlings were significantly improved when penoxsulam and clomazone were applied simultaneously on day 13 after sowing the rice, compared with the treatment with penoxsulam alone.

Evaluation of herbicidal Activity in Water-seeded Rice

The results presented in table 3 demonstrate that clomazone does not antagonize or reduce the activity of penoxsulam on the three weeds with respect to weed control by ECHOR, LEFFA and CYPDI.

Table 1-visual Rice Damage%

(1) Visual rice damage (%)

(2) Visual rice damage at day 14 post-treatment (%)

(3) Visual rice damage (%)

ORYSA ═ rice (Oryza sativa) 'M205' (rice)

Obs ═ observed value

Exp is expected calculated value

g ai/ha ═ g active ingredient/ha

TABLE 2 reduction of rice seedlings%

(1) Visual reduction of rice seedlings at day 7 after treatment (%)

(2) Visual reduction of rice seedlings at day 14 after treatment (%)

(3) Visual reduction of rice seedlings at day 21 after treatment (%)

ORYSA ═ rice (Oryza sativa) 'M205' (rice)

Obs ═ observed value

Exp is expected calculated value

g ai/ha ═ g active ingredient/ha

TABLE 3 weed control%

(1) Visual weed control for ECHOR at day 27 after treatment (%)

(2) Visual weed control on LEFFA on day 27 after treatment (%)

(3) Visual weed control (%) CYPDI on day 27 post-treatment

Echor ═ Echinocroa oryzae (aquatic weeds)

LEFFA ═ stephania root (Leptochloa fascicularis, sprangletop)

Cypdi (Cyperus difformis, smallflower umbella secdge)

Obs ═ observed value

Exp is expected calculated value

g ai/ha ═ g active ingredient/ha

Claims (6)

1. A method for protecting water-seeded and transplanted paddy rice from the harmful effects of penoxsulam and its agriculturally acceptable salt derivatives, which comprises applying clomazone as a safener directly to the water of said water-seeded or transplanted paddy rice.

2. The method of claim 1 wherein penoxsulam and clomazone can be applied separately or together as components in a multi-component herbicide system.

3. The method of claim 2, wherein the weight ratio of penoxsulam to clomazone is from 1:2 to 1: 100.

4. The method of claim 3, wherein the weight ratio of penoxsulam to clomazone is from 1:5 to 1: 20.

5. The method of claim 2 wherein penoxsulam is applied at a rate of 5 to 60g/ha and clomazone is applied at a rate of 100 to 650 g/ha.

6. The method of claim 5 wherein penoxsulam is applied at a rate of 40g/ha and clomazone is applied at a rate of 220g/ha to 450 g/ha.