EA043622B1 - HERBICIDE - Google Patents

Description

Scope of the invention

The invention relates to the selective control of weeds in agricultural crops, such as cereals. In particular, the invention relates to the use of a herbicide in a crop growing area for the purpose of selectively controlling weeds in that area. The invention also relates to methods for selectively controlling the growth of weeds in a crop growing area using a herbicide. The invention further relates to an area for growing a grain crop, to which a selective herbicide is applied. The herbicide used in the present invention is napropamide.

Prerequisites for creating the invention

Selective control of weeds in commercial crops such as cereals is a key challenge in modern agriculture. Weeds typically compete with crops such as cereals for nutrients, water, light and space, and therefore, if weeds are not controlled in crops, crop yields may be reduced. Weeds can also be a source of pests and diseases which, when transferred to crops, can also reduce crop yields. Moreover, weed seeds may be accidentally collected together with the desired crop, which may require additional treatment or treatment of the harvested crop or even, in extreme cases, its complete destruction. Therefore, there is a clear need for effective herbicides capable of controlling the growth of weeds to prevent contamination of agricultural crops such as cereals.

Many herbicides have been developed to control the growth of unwanted plants such as weeds. A number of such herbicides have previously been described to be effective in controlling all plant material with which they come into contact. Such herbicides include paraquat, glufosinate, glyphosate and the like. However, these herbicides are not selective and thus cannot be used for selective control of weeds in crops such as cereals, since such herbicides kill or damage the crop along with the weed. Thus, to solve this problem, it is necessary to use selective herbicides that can control weed growth while protecting the crop.

A well-known herbicide is napropamide, also known as N,N-diethyl-2-(αnaphthoxy)propionamide. Napropamide is most often sold under the brand name Devrinol. The structure of napropamide is shown in formula (I) below.

o ⁿ 3C\ A ^CH ₃ eg ¹

FORMULA (I)

Napropamide contains a chiral carbon atom and therefore exists in two stereoisomeric forms, one of which is the D-isomer, also known as the (R)-isomer, and the other form is the L-isomer, also known as the (S)-isomer . The D-isomer (D-napropamide) is also called napropamide-M and its structure is shown in formula (II)

FORMULA (II)

Napropamide-M can be prepared by any suitable method known in the art, for example the methods described in WO 2009/004642.

Unless otherwise specified, and as further described below, the term napropamide as used herein refers to N,N-diethyl-2-(α-naphthoxy)propionamide, or an isomer thereof, or a mixture of such isomers. Accordingly, unless otherwise indicated or unless otherwise clearly evident from the context, the term napropamide may refer to a mixture of D-napropamide and L-napropamide. The mixture may be, for example, a racemic mixture (i.e. a 1:1 mixture of D-napropamide and L-napropamide). The term napropamide also covers the pure isomers of N,N-diethyl-2-(α-naphthoxy)propionamide, including, for example, D-napropamide.

- 1 043622

It has previously been shown that napropamide can be used to selectively control the growth of dicotyledonous weeds. For example, EP 277397 A1 describes how napropamide can be used to selectively control dicotyledonous weeds in crops such as oilseed rape, strawberries, black currants, gooseberries, raspberries, field trees, shrubs, broccoli, cabbage, asparagus cabbage, cauliflower, kale and Brussels sprouts. However, EP 277397 A1 clarifies that napropamide has low activity in controlling monocotyledonous weeds in such crops. EP 277397 A1 also makes no mention of selective weed control in monocotyledonous crops such as cereals. Thus, there continues to be a critical need for methods to control weeds, such as monocots, in crops, especially grain crops.

Summary of the invention

The inventors of the present invention have surprisingly discovered that napropamide selectively inhibits the growth of weeds, such as monocotyledonous weeds, in cereal crops. As described in more detail herein, the present inventors have shown that application of napropamide to monocot grain crops selectively spares the crop itself while selectively affecting weeds, including common grass weeds. This finding is particularly surprising given the fact that both cereal crops and grass weeds are monocots. Thus, not only was it surprising that napropamide could be safely used as a herbicide in cereal crops, i.e. without destroying the crop itself, but what was also particularly surprising was that napropamide was able to simultaneously inhibit the growth of cereal weeds. Like cereals, such weeds are monocots, and finding a herbicide that exhibits selectivity between different classes of monocots is challenging because such selectivity cannot be predicted. It was therefore surprising that napropamide was able to control one class of monocots, namely grass weeds, while at the same time sparing another class of monocots, i.e. grain crops.

Thus, the invention proposes the use of napropamide for selective control of weeds in a crop growing area; wherein the grain crop is present on the site, or is planted on the site after applying said napropamide to the site.

The invention also provides a method for selectively controlling weeds in a crop growing area, the method comprising applying napropamide to the area, wherein the crop is present on the area or is planted on the area after said napropamide is applied to the area.

Additionally, an area for growing a grain crop is provided, where both weeds and the grain crop are present in the area, and a herbicide for selective weed control is applied to the area, wherein said herbicide consists of or contains napropamide.

Brief description of graphic materials

In fig. Figure 1 shows normalized plant growth after application of herbicides as described in Example 1.

In fig. Figure 2 shows additional normalized plant growth after herbicide application as described in Example 1.

Detailed Description of the Invention

As explained above, the invention provides the use of napropamide for selective control of weeds in a crop growing area; wherein the grain crop is present on the site, or is planted on the site after applying said napropamide to the site.

The term selective control means that the herbicide is able to control the growth of one plant species while allowing the growth of another. Thus, selective weed control means that the growth of weeds is controlled, but the growth of other non-weed plants, such as crops, is not controlled or is controlled to a significantly lesser extent than the growth of weeds. Generally, weed control involves preventing weeds from germinating, establishing or growing. Weed control often involves slowing or stopping the growth of weeds. Weed control may involve preventing or slowing root development. Inhibiting the growth of weeds may include inhibiting cell division, thereby preventing the development of roots or leaves, especially roots. Weed control may include preventing, suppressing or delaying the germination of weed seeds. As a result of weed control, growth after application of the herbicide may be reduced compared to weed growth in the absence of the herbicide. Often, weed growth after application of the herbicide is suppressed by at least 50%, such as at least 60%, such as at least 70%, more commonly at least 80%, such as at least 90%, such as at least 95%, at least 97%, at least 98%, or at least 99% compared to weed growth in the absence of the herbicide. In the invention, the herbicide is

- 2 043622 mid. Napropamide, as defined herein and described in more detail below, can be administered as a pure substance or in the form of a composition containing one or more additional components, such as one or more agrochemically acceptable excipients, diluents, adjuvants and/or antidotes; and/or together with an additional active agent, for example etofumezate, flufenacet and/or pendimethalin.

Accordingly, selective weed control in a crop growing area generally involves preventing the germination, establishment or growth of the weed while not preventing the germination, establishment or growth of the crop. For example, the growth of a crop after application of a herbicide may be at least 50% of the growth of the crop in the absence of the herbicide. Even more often, the growth of the crop after application of the herbicide may be at least 60%, for example at least 70%, more often at least 80%, for example at least 90%, for example at least 95%, at least 97%, at least 98%, at least 99% or even 100% of the growth of the crop in the absence of the herbicide. Most often, the application of a herbicide does not have a significant effect on the growth of the grain crop, but at the same time significantly inhibits the growth of weeds.

In the invention, the crop growing area is located in the area of the crop for which selective weed control is required. In the invention, the area may be, for example, a container such as a pot or grow bag, a flower bed or a field. Typically, in the invention, the area is a field. A site is any location where a crop is or will be planted after the herbicide has been applied. A site is an area where weed growth is observed or expected in the absence of herbicide application.

In the invention, the grain crop planted or planned to be planted on the site may be any grain crop. In the invention, the term crop generally refers to a variety of desired crop plants, i.e. cereal plants growing on the site, but can also refer to only one desired agricultural plant, i.e. to one grain plant growing on the site. Thus, the term crop covers plants in which the target part of the plant (eg seeds) is already developed, or in which the target part of the plant is not yet developed, such as young or immature plants.

As will be appreciated by those skilled in the art, cereal crops are typically monocotyledonous species. Thus, the cereal crop is typically a monocotyledonous cereal crop. In the invention, the cereal crop is typically selected from wheat, barley, rice, corn, sorghum, oats, rye, millet, triticale and fonno. Sometimes the grain crop is selected from barley, rice, corn, sorghum, oats, rye, millet, triticale and fonyo. The crop may not be wheat. Typically, in the invention, the cereal crop is selected from wheat, barley, rice and corn. The most commonly used cereal crops in the invention are wheat, rice and corn. Even more commonly in the invention, the cereal crop is selected from wheat and corn. The most commonly used cereal crop in the invention is wheat.

In the invention, if the cereal crop is wheat, the wheat may be winter wheat or spring wheat. Generally, the wheat is winter wheat. Those skilled in the art will appreciate that winter wheat are varieties of wheat that are planted in the fall and therefore grow during the winter. A typical winter wheat is bread wheat (winter wheat), which has the code TRZAW according to the European and Mediterranean Plant Protection Organization (EPPO) classification. Thus, winter wheat may be TRZAW. Winter wheat germinates and develops into young plants that remain in the vegetative stage during the winter and resume growth in early spring. For winter wheat, the physiological heading stage is typically delayed until the plant has undergone vernalization, typically after a period of about 30 to about 60 days at a temperature of about 0 to 5°C.

In the invention, the crop can be planted at any suitable depth. For example, a crop may be planted in an area to a depth of at least 1 cm. More commonly, a grain crop is planted in an area at a depth of at least 2 cm. The inventors of the present invention have surprisingly discovered that when planting crops at a depth of at least 1 cm, such as at least 2 cm, the selectivity of napropamide for the crop (ie, the degree to which the crop is not affected by napropamide) is improved. For example, the crop may advantageously be planted to a depth of at least 1 cm, such as at least 2 cm, more typically at least 3 cm.

In the invention, the weeds that are selectively controlled in the crop growing area are generally monocotyledonous weeds. Thus, the invention generally proposes the use of napropamide for the selective control of monocotyledonous weeds in

- 3 043622 plot for growing monocotyledonous grain crops; wherein the monocotyledonous grain crop is present on the site, or is planted on the site after applying said napropamide to the site. In other words, the invention provides means for selective control of monocotyledonous weeds in monocotyledonous crops.

The weed genus to be selectively targeted in the present invention is generally selected from Alopecurus (eg Alopecurus myosuroides), Echinochloa (eg Echinochloa crus-galli L), Bromus (eg Bromus secalinus or Bromus tectorum L), Lolium (eg Lolium perenne L), Poa and Setaria (eg Setaria glauca L. Beauv.).

For example, a weed may be one or more of the following species:

Alopecurus aequalis, Alopecurus albovii, Alopecurus anatolicus, Alopecurus apiatus, Alopecurus arundinaceus, Alopecurus aucheri, Alopecurus baptarrhenius, Alopecurus bonariensis, Alopecurus borii, Alopecurus bornmuelleri, Alopecurus brachystachus, Alopecurus bulbosus, Alopecurus carolinianus, Alopecur us creticus, Alopecurus dasyanthus, Alopecurus davisii, Alopecurus geniculatus , Alopecurus gerardii, Alopecurus glacialis, Alopecurus x haussknechtianus, Alopecurus heliochloides, Alopecurus himalaicus, Alopecurus hitchcockii, Alopecurus japonicas, Alopecurus laguroides, Alopecurus lanatus, Alopecurus longiaristatus, Alopecurus magellanicus, Alopecurus x marssonii, Alope curus mucronatus, Alopecurus myosuroides, Alopecurus nepalensis, Alopecurus x plettkei, Alopecurus ponticus, Alopecurus pratensis, Alopecurus rendlei, Alopecurus saccatus, Alopecurus setarioides, Alopecurus textilis, Alopecurus turczaninovii, Alopecurus x turicensis, Alopecurus utriculatus, Alopecurus vaginatus, Alopecurus x winklerianus, Bromus aleutensis, Bromus alopecuros, Bro mus anomalus, Bromus arenarius, Bromus

- 4 043622 arizonicus, Bromus arvensis, Bromus berteroanus, Bromus biebersteinii, Bromus briziformis, Bromus bromoideus, Bromus carinatus, Bromus cabrerensis, Bromus catharticus, Bromus ciliates, Bromus ciliates (inc. ssp. ciliates and richardsonii), Bromus commutatus, Bromus danthoniae, Bromus diandrus, Bromus erectus, Bromus exaltatus, Bromus fibrosus, Bromus frigidus, Bromus frondosus, Bromus grandis, Bromus grossus, Bromus hordeaceus, Bromus hordeaceus (inc. ssp. ferronii, hordeaceus, molliformis, pseudothominii and thominei), Bromus inermis, Bromus inermis (inc. ssp. inermis and pumpellianus), Bromus interruptus, Bromus japonicas, Bromus kalmia, Bromus kinabaluensis, Bromus koeieanus, Bromus kopetdagensis, Bromus laevipes, Bromus lanatipes, Bromus lanceolatus, Bromus latiglumis, Bromus Lepidus, Bromus luzonensis, Bromus macrostachys, Bromus madritensis, Bromus mango, Bromus marginatus, Bromus maritimus, Bromus mucroglomis, Bromus nottowayanus, Bromus orcuttianus, Bromus pacificus, Bromus polyanthus (inc. ssp. paniculatus and polyanthus), Bromus porter, Bromus pseudolaevipes, Bromus pseudosecalinus, Bromus pseudothominii, Bromus pubescens, Bromus ramosus (inc ssp. benekii and ramosus), Bromus rigidus, Bromus scoparius, Bromus secalinus, Bromus sitchensis, Bromus squarrosus, Bromus stamineus, Bromus sterilis, Bromus suksdorfii, Bromus tectorum, Bromus texensis, Bromus vulgaris, Bromus willdenowii, Echinochloa brevipedicellata, Echinochloa callopus, Echinochloa chacoensis, Echinochloa colona, Echinochloa crus-galli, Echinochloa crus-pavonis, Echinochloa elliptica, Echinochloa glabrescens, Echinochloa haploclada, Echinochloa helodes , Echinochloa holciformis, Echinochloa inundata, Echinochloa jaliscana, Echinochloa jubata, Echinochloa kimberleyensis, Echinochloa lacunaria, Echinochloa macrandra, Echinochloa muricata, Echinochloa obtusiflora, Echinochloa oplismenoides, Echinochloa oryzoides, Echinochloa paludi gena, Echinochloa picta, Echinochloa pithopus, Echinochloa polystachya, Echinochloa praestans, Echinochloa pyramidalis, Echinochloa rotundiflora, Echinochloa telmatophila, Echinochloa turneriana, Echinochloa ugandensis, Echinochloa walteri, Lolium arundinaceum, Lolium canariense, Lolium giganteum, Lolium x hybridum, Lolium mazzettianum, Lolium multiflorum, Lolium perenne L., Lolium persicum, Lolium pratense, Lolium remotum, Lolium rigidum, Lolium saxatile, Lolium temulentum L, Setaria acromelaena, Setaria alonsoi, Setaria apiculata, Setaria appendiculata, Setaria arizonica, Setaria atrata, Setaria australiensis, Setaria austrocaledonica, Setaria barbata, Setaria barbinodis, Setaria bathiei, Setaria cernua, Setaria chondrachne, Setaria cinerea, Setaria clivalis, Setaria cordobensis, Setaria corrugate, Setaria dielsii, Setaria elementii, Setaria faberi, Setaria fiebrigii, Setaria finite, Setaria forbesiana, Setaria glauca L. Beauv., Setaria

- 5 043622 globulifera, Setaria gracillima, Setaria grandis, Setaria grisebachii, Setaria guizhouensis, Setaria hassleri, Setaria homonyma, Setaria humbertiana, Setaria hunzikeri, Setaria incrassate, Setaria intermedia, Setaria italic, Setaria jaffrei, Setaria kagerensis, Setaria lachnea, Setaria latifolia, Setaria leucopila, Setaria liebmannii, Setaria lindenbergiana, Setaria longipila, Setaria longiseta, Setaria macrosperma, Setaria macrostachya, Setaria madecassa, Setaria magna, Setaria megaphylla, Setaria mendocina, Setaria mildbraedii, Setaria montana, Setaria nepalense, Setaria nicorae, Setaria nigrirostris, Setaria oblongata , Setaria obscura, Setaria oplismenoides, Setaria orthosticha, Setaria palmeri, Setaria palmifolia, Setaria pampeana, Setaria paraguayensis, Setaria parodii, Setaria parviflora, Setaria paspalidioides, Setaria pauciflora, Setaria paucifolia, Setaria perrieri, Setaria petiolata, Setaria pflanzii, Setaria plicata, Setaria poiretiana, Setaria pseudaristata, Setaria pumila, Setaria queenslandica, Setaria restioidea, Setaria rigida, Setaria roemeri, Setaria rosengurttii, Setaria sagittifolia, Setaria scabrifolia, Setaria scandens, Setaria scheelei, Setaria scottii, Setaria seriata, Setaria setosa, Setaria sphacelata, Setaria stolonifera, Setaria submacrostachya, Setaria sulcata, Setaria surgens, Setaria tenacissima, Setaria tenax, Setaria texana, Setaria vaginata, Setaria vatkeana, Setaria verticillata, Setaria villosissima, Setaria viridis, Setaria vulpiseta, Setaria welwitschii and Setaria yunnanensis.

Most commonly, the weed targeted by the invention belongs to the genus Alopecurus. The most common weed is Alopecurus myosuroides. According to the EPPO classification, Alopecurus myosuroides has the code ALOMY, therefore it is also called ALOMY. For example, the weed may be ALOMY (S line) or ALOMY (Peldon multi-R (resistant) line).

One useful aspect of the invention is the selective control of weeds in cereal crops, the weed being resistant to control by conventional selective herbicides other than napropamide. Those skilled in the art will appreciate that a weed resistant to control by a given substance need not be completely resistant to the use of the substance. Moreover, a weed resistant to control by a given substance may be able to grow in the presence of the substance, although at a lower rate than in the absence of the substance. A weed that is resistant to control by a given substance but not resistant to control by napropamide may grow better in the presence of an effective amount of the substance than in the presence of an effective amount of napropamide. In other words, napropamide may be more effective at controlling weed growth than another substance.

For example, a herbicide to which a given weed is resistant may typically exhibit less than 97% effectiveness against that weed; in other words, at least 3% of the weeds to which an effective amount of the herbicide has been applied can survive the application of the herbicide. More typically, such a herbicide may exhibit less than 95% effectiveness against weeds, such as less than 90% effectiveness, such as less than 80% effectiveness, such as less than 70% effectiveness, such as less than 60% effectiveness, such as less than 50% effectiveness, such as less than 40% effectiveness, or even efficiency less than 35%. In other words, typically at least 5% of the weeds to which an effective amount of the herbicide has been applied survive application of the herbicide, e.g., at least 10% of the weeds, e.g., at least 20% of the weeds, e.g., at least 30 % of the weeds, e.g., at least 40% of the weeds, e.g., at least 50% of the weeds, e.g., at least 60% of the weeds, or even more than 65% of the weeds, to which an effective amount of the herbicide has been applied can survive the application herbicide. In contrast, such weeds are generally more susceptible to control by napropamide; for example, napropamide is generally capable of inhibiting the growth of such resistant weeds by at least 60%, more commonly by at least 70%, more commonly by at least 80%, e.g. by at least 90%, e.g. by at least 95%, at least 97%, at least 98%, or at least 99% compared to weed growth in the absence of napropamide. For example, against some weeds, conventional herbicides are less than 50% effective, e.g. less than 40% effective, or even less, e.g. less than 35% effective, while napropamide is at least 60% effective, e.g. at least 70% effective, the efficiency is at least 80% or at least 90%.

Those skilled in the art will appreciate that the relative effectiveness of napropamide and other herbicides depends in part on the amount of the respective herbicide that is applied to the site. Generally, the effectiveness of napropamide can be increased by increasing the amount of napropamide applied to the area. Often, smaller amounts of napropamide can provide significant control of resistant weeds (e.g., at least 90% control,

- 6 043622 for example, at least 95% control, for example, at least 97%, 98% or 99% control, while a larger amount of a conventional herbicide may not provide such levels of control. For example, as further discussed herein, the inventors have demonstrated that napropamide can be much more effective than conventional herbicides such as Xerton and can provide improved control compared to herbicides such as Trooper/Malibu. Additionally, it has surprisingly been discovered that this control can generally be successfully achieved with significantly lower application rates of napropamide compared to herbicides such as Trooper/Malibu.

Non-limiting examples of selective control of resistant weeds by napropamide compared to other conventional herbicides are provided in the Examples.

Often, the weed that is selectively targeted by the invention is resistant to control by ethophumesate, flufenacet and/or pendimethalin. Typically, the weed that is selectively targeted by the invention is resistant to control by etofumezate, flufenacet and/or pendimethalin when the etofumesate, flufenacet and/or pendimethalin are applied in accordance with best practices and the manufacturer's instructions. For example, a weed may be resistant to control by ethofumesate when applied at 0.6 L/ha of a suspension concentrate containing 417 g/L of ethofumesate. A suspension concentrate containing 417 g/l ethofumesate is commercially available under the trade name Xerton (United Phosphorus). Accordingly, the weed may be resistant to growth control by Xerton, for example, when applied at about 0.1 to about 2 L/ha, for example, when applied at about 0.6 L/ha. The weed may be resistant to flufenacet control when applied at 2.5 l/ha of an emulsifiable concentrate containing 60 g/l flufenacet and 300 g/l pendimethalin. An emulsifiable concentrate containing 60 g/L flufenacet and 300 g/L pendimethalin is commercially available under the trade name Trooper (Basf) and under the trade name Malibu (Basf). Accordingly, the weed may be resistant to growth control by Trooper and/or Malibu, for example, when applied at about 1 to about 10 L/ha, for example, when applied at about 2.5 L/ha.

For example, in some embodiments, the weed may be controlled by Xerton herbicide by less than about 60%, such as less than about 50% or less than 40%, and/or may be controlled by Malibu herbicide by less than 98% or less than 97% and may be controlled by more than 97% by napropamide (for example, greater than 98% or greater than 99%) when applied at an effective concentration, for example in an amount corresponding to about 10 g/ha to about 1 kg/ha napropamide or Dnapropamide, more often in an amount , corresponding to about 400 g/ha to about 700 g/ha napropamide or D-napropamide.

Typically, in the invention, the herbicide is applied to the crop growing area prior to the emergence of said weed. For example, the herbicide may be applied to an area at a known point after plowing or based on the growth of reference plants other than the weed that have specific growth characteristics that can be monitored and correlated with the likely emergence of the weed.

In another embodiment of the invention, the herbicide can be applied to the specified area after partial growth of the specified weed. The herbicide can be applied to the area after the weed has emerged.

A well-known measure of plant growth is the BBSN scale (Federal Biological Office, Office for the Protection of Plant Varieties and the Chemical Industry). The BBSN scale is a scale used to determine the stages of phenological development of a plant. Several BBCH scales have been developed for a number of species, including cereals and weeds. The BBSN scale uses a decimal code system divided into primary and secondary growth stages.

Those skilled in the art will appreciate that the BBCH _weed scale and the BBCH _grass scale determine plant growth as follows:

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BBSN number Weed Cereal 00 Dry seed Dry seed (kernel) 01 Beginning of seed saturation with moisture Beginning of seed saturation with moisture 02 03 Completion of seed saturation with moisture Completion of seed saturation with moisture 04 05 Emergence of the primary radicle (root) from the seed The appearance of the primary root from the grain 06 Elongation of the primary root, formation of root hairs and/or lateral roots The primary root is elongated, root hairs and/or lateral roots are visible 07 Hypocotyl with cotyledons or shoot breaking through the seed coat Emergence of coleoptile from grain 08 Hypocotyl with cotyledons or shoot germination to the soil surface 09 Emergence: cotyledons break through the soil surface Emergence: coleoptile breaks through the soil surface (cracking stage) 10 Emergence of the first true leaf from the coleoptile First leaf through coleoptile eleven First true leaf, pair of leaves, or open whorl Opened first sheet 12 2 true leaves, pairs of leaves or open whorls 2 sheets opened 13 3 true leaves, pairs of leaves or open whorls 3 sheets opened 14 4 true leaves, pairs of leaves or open whorls 4 sheets opened 15 5 true leaves, pairs of leaves or open whorls 5 sheets opened 16 6 true leaves, pairs of leaves or open whorls 6 sheets opened 17 7 true leaves, pairs of leaves, or open whorls 7 sheets opened 18 8 true leaves, pairs of leaves, or open whorls 8 sheets opened 19 9 or more true leaves, pairs of leaves, or open whorls 9 or more open leaves

BCCH values greater than 19 represent plant growth after the main growth stage 2, during which side shoots (tillering) are formed.

Typically, in the invention, when a herbicide is applied to a site after said weed has partially grown, the weed will typically grow to a growth stage of BBCH _weed 01 to BBCH _weed 19. More commonly, the weed will grow to a growth stage of BBCH _weed 01 to BBCH _weed 11. For example, the weed may grow to the growth stage from BBSN _weed 09 to BBSN _weed 14, for example approximately to BBSN _weed 11.

Typically, in the invention, the herbicide is applied to the crop growing area before the crop emerges. For example, the herbicide can be applied to the site before planting, during planting, or in most cases after planting and before crop emergence to prevent weed emergence. Thus, the herbicide may be applied to the site before planting the crop (e.g., before sowing crop seeds), during planting of the crop (e.g., while sowing crop seeds), or, in most cases, after planting the crop (e.g., after sowing seeds of an agricultural crop) and before the germination of the agricultural crop.

In another embodiment, the herbicide may be applied to the site after germination

- 8 043622 economic crops. Additionally or alternatively, the herbicide can be applied to the site after partial growth of the specified crop. For example, a crop may be grown to a growth stage of BBCH _cereal 01 to BBCH _cereal 19. More commonly, a crop may be grown to a growth stage of BBCH _cereal 01 to BBCH cereal 11. For example, a crop may be grown to a growth stage of BBCH cereal 09 to BBCH _cereal 14, for example approximately up to BBSN _cereal 11.

Typically, site application of a herbicide involves applying the herbicide to the soil of the site. Typically the herbicide is applied to the surface of the soil. However, when applying the herbicide to an area after the weed has partially grown, especially if the weed has grown to a post-emergence growth stage, such as the BBCH _weed 09 to BBCH _weed 19 growth stage, the herbicide can be applied directly to the weed. Typically, the herbicide is applied by spraying.

As stated above, the napropamide used in the invention may be racemic napropamide, i.e. it may be a mixture of equal amounts of D-napropamide (also known as napropamide-M or (R)-napropamide) and L-napropamide (also known as (S)-napropamide). However, of the two isomers of napropamide, only the D-isomer is known to have significant herbicidal activity; thus, the use of D-napropamide is preferred over racemic napropamide. Therefore, often the napropamide used in the invention contains more D-napropamide than L-napropamide. For example, the molar ratio of D-napropamide to Lnapropamide in the napropamide used in the invention may be greater than 1:1. The molar ratio of D-napropamide to L-napropamide may be, for example, at least 3:2, or, for example, at least 7:3, for example, at least 4:1 or at least 9:1. The napropamide used in the invention may be, for example, D-napropamide. Accordingly, the herbicide is often substantially free or free of L-napropamide ((S)-napropamide). In other words, the invention does not exclude compositions containing L-napropamide, in which the active ingredient is D-napropamide. However, as a rule, the herbicide in the invention does not contain L-napropamide. Thus, the napropamide used in the invention may consist of D-napropamide.

In the present invention, the herbicide can be applied in any suitable amount to achieve weed control on the site. The herbicide can, for example, be applied in an amount corresponding to about 10 g/ha to about 2 kg/ha D-napropamide, or, for example, about 10 g/ha to about 1.5 kg/ha D-napropamide. For example, the herbicide can be applied in an amount corresponding to from about 10 g/ha to about 1 kg/ha of D-napropamide. For example, the herbicide can be applied from a suspension concentrate containing about 450 g/L D-napropamide. Thus, the application of such a composition in an amount of 0.1 l/ha corresponds to the application of 45 g/ha of D-napropamide. Similarly, the application of such a composition in an amount of 0.4 l/ha corresponds to the application of 180 g/ha of D-napropamide; the application of such a composition in an amount of 0.7 l/ha corresponds to the application of 315 g/ha of D-napropamide; application of such a composition in an amount of 1 l/ha corresponds to the application of 450 g/ha of D-napropamide; application of such a composition in an amount of 1.4 l/ha corresponds to the application of 630 g/ha of D-napropamide; and the application of such a composition in an amount of 1.7 l/ha corresponds to the application of 765 g/ha of D-napropamide, etc.

More commonly, in the invention, the herbicide is applied in an amount corresponding to about 400 g/ha to about 700 g/ha D-napropamide. The inventors have found that such application levels are particularly advantageous because long-term crop impact (eg, measured from about 25 to about 54 days after anthesis (DAA)) can be improved at such application levels; At the same time, activity against weeds is not reduced. For example, application rates corresponding to about 1 to about 1.5 L/ha of a suspension concentrate containing about 450 g/L D-napropamide have been found to be particularly preferred.

It should be emphasized that each amount of napropamide in g or kg indicated in the previous two paragraphs represents the amount of the D-isomer, i.e. D-napropamide, and not the total amount of napropamide, including both D-napropamide and L-napropamide. As described above herein, in addition to D-napropamide, the herbicide may or may not contain L-napropamide (eg, it may contain racemic napropamide). If the herbicide does not contain L-napropamide, i.e. if the napropamide used in the herbicide composition is only D-napropamide, then each value given above in the two previous paragraphs regarding the amount of D-napropamide will be the same as the total amount of napropamide in the herbicide. On the other hand, if the napropamide used in the herbicide is a racemic napropamide and therefore contains D-napropamide and L-napropamide in a 1:1 molar ratio, each value given above in the previous two paragraphs for the amount of D-napropamide will be half of the total amount of napropamide in the applied herbicide, including both D-napropamide and Lnapropamide.

For example, in some embodiments, the napropamide used in the present invention is racemic napropamide, and the total amount of napropamide, including both D- and L-isomers, will be twice the amount specified above for D-napropamide. Thus, in some embodiments, the napropamide used in the herbicide is race

- 9 043622 racemic napropamide, and the herbicide can be applied to achieve control of weeds on the site in an amount corresponding to from about 20 g/ha to about 4 kg/ha racemic napropamide, or, for example, from about 20 g/ha to about 3 kg/ ha racemic napropamide. For example, the herbicide can be applied in an amount corresponding to about 20 g/ha to about 2 kg/ha of racemic napropamide. For example, the herbicide can be applied from a suspension concentrate containing about 450 g/L racemic napropamide. Thus, the application of such a composition in an amount of 0.2 l/ha corresponds to the application of 90 g/ha of racemic napropamide. Similarly, the application of such a composition in an amount of 0.8 l/ha corresponds to the application of 360 g/ha of racemic napropamide; the application of such a composition in an amount of 1.4 l/ha corresponds to the application of 630 g/ha of racemic napropamide; application of such a composition in an amount of 2 l/ha corresponds to the application of 900 g/ha of racemic napropamide; application of such a composition in an amount of 2.8 l/ha corresponds to the application of 1260 g/ha of racemic napropamide and application of such a composition in an amount of 3.4 l/ha corresponds to the application of 1530 g/ha of racemic napropamide, etc.

In some embodiments, the napropamide is racemic napropamide and the herbicide is applied in an amount corresponding to about 800 g/ha to about 1400 g/ha racemic napropamide. Such application levels are particularly preferred because long-term crop impact (eg, measured from about 25 to about 54 days after anthesis (DAA)) can be improved at such application levels; At the same time, activity against weeds is not reduced. For example, application rates corresponding to about 2 to about 3 L/ha of a suspension concentrate containing about 450 g/L racemic napropamide are particularly preferred.

In the invention, napropamide is often contained in a composition containing at least one agronomically acceptable excipient, diluent, adjuvant and/or antidote in addition to napropamide. Agronomically acceptable excipients may be selected from carriers, inert materials, organic or inorganic solvents, minerals, mixed solvents, wetting agents and/or emulsifying agents, adhesives, anti-caking agents, deflocculating agents, and the like. Such herbicide composition may be formulated in form of solid and liquid compositions. Agronomically acceptable adjuvants may be selected from preservatives, surfactants, wetting agents, emulsifying agents and dispersing agents. Agronomically acceptable diluents may be selected from liquid diluents such as water and solid diluents such as clay, diatomaceous earth, bentonite and silica. Liquid diluents are most often used in the invention. Water is usually used as a diluent. Agronomically acceptable safeners may act by directly interacting with biochemical targets or herbicide receptor proteins in crop plants; by reducing the amount of herbicides reaching crop plants in active form, either by reducing the uptake or translocation of herbicides, and/or by increasing the degradation of herbicides to less active or immobile metabolites.

In the invention, napropamide is often contained in a composition further containing an additional active agent. The additional active agent is typically another herbicide, such as a second herbicide that is selective for dicotyledonous weeds. A broad spectrum herbicide can also be used. The additional active agent is generally not active against cereal crops. The additional active agent may, for example, contain etofumezate, flufenacet and/or pendimethalin.

The invention also provides a method for selectively controlling weeds in a crop growing area, the method comprising applying napropramide to the area, the crop being present on the area or being planted on the area after said napropamide has been applied to the area. In such aspects of the invention, a weed generally meets the definition herein; the grain crop generally meets the definition herein; napropramide is generally as defined herein and/or application of napropramide is generally as defined herein. The method may include applying a herbicide to an area and then planting a crop, or may involve planting a crop and then applying a herbicide.

The invention also provides an area for growing a grain crop, wherein both weeds and the crop are present in the area, and wherein a herbicide for selective weed control is applied to the area, wherein the herbicide consists of or contains napropamide. In such aspects of the invention, a weed generally meets the definition herein; the grain crop generally meets the definition herein; napropramide is generally as defined herein and/or application of napropramide is generally as defined herein. The site, which typically contains soil suitable for growing a crop, in addition to weeds, crop and herbicide composition, may also

- 10 043622 be as further defined herein. For example, the area may be a container such as a pot or grow bag, a flower bed, or a field.

The invention also provides a kit containing napropamide for selective control of weeds in a crop growing area and instructions for use. Directions for use typically include instructions for applying napropamide to the area. The grain crop is present on the plot, or it is planted on the plot after applying the specified napropamide to the plot.

As a rule, the set contains:

i) a first component containing napropamide;

ii) a second component containing an agrochemically acceptable excipient, diluent, adjuvant and/or antidote;

and optionally further contains:

iii) a third component containing an additional active agent; and/or iv) instructions for use.

Typically, the instructions for use contain instructions for the user to mix the components of the kit. Typically, the instructions for use contain instructions for the user to mix the components of the kit before applying the components of the kit to the area.

Often the kit components are packaged separately. However, the invention is not limited to kits in which the components are packaged separately. For example, the first component and the second component may be packaged or prepared together. If a third component is present, as described above, then the first component may be packaged or prepared together with the third component. In an alternative embodiment, the second component may be packaged or prepared together with the third component. In yet another embodiment, the first component, the second component, and the third component may be packaged or prepared together.

In embodiments of the kit of the invention in which the first component and the third component are packaged separately, the first component and the third component may be mixed in a tank prior to application to the site. As a rule, such application to the site is carried out by spraying.

In embodiments of the kit of the invention in which the first component and the third component are packaged together, other components, such as the second component, may be packaged separately. In such embodiments, the components (i.e., (i) the first component and the third component; and (ii) the second component) may be mixed in a tank prior to application to the site. As a rule, such application to the site is carried out by spraying.

Thus, the kit of the present invention typically:

a) a third component is present containing the additional active agent, and said first component and said third component are packaged separately, preferably the first component and said third component are in a form suitable for tank mixing prior to application to the site; or

b) a third component containing an additional active agent is present, and said first component and said third component are formulated together, preferably the first component and said third component are in a form suitable for tank mixing with said second component before application to the site;

Typically, in the kit of the invention, said napropamide is D-napropamide.

Typically, in the kit of the invention, if there is a third component containing an additional active agent, said additional active agent is selected from etofumezate, flufenacet and/or pendimethalin.

Typically, the instructions for use will instruct the user how to apply the first component (ie, napropamide or a composition containing napropamide) to a crop growing area; moreover, the grain crop is present on the site, or it is planted on the site after the specified application. Often, the instructions for use will show the user how to apply the first component (ie, napropamide or a composition containing napropamide) to the crop site; Moreover, both weeds and grain crops are present on the site. In other words, the instructions for use typically show the user how to apply the first component (ie, napropamide or a composition containing napropamide) to a crop and monocot weed site.

Typically, the instructions for use will instruct the user how to apply the first component (i.e., napropamide or a composition containing napropamide) to a crop that is planted in an area at a depth of at least 1 cm, such as at least 2 cm.

Typically, the instructions for use will show the user how to apply the first component (ie, napropamide or a composition containing napropamide) to an area where Alopecurus weed is present. Often, the instructions for use will show the user how to apply the first component (i.e., napropamide or a composition containing napropamide) to an area in which a crop and a weed grow, wherein the weed is resistant to control by conventional

- 11 043622 selective herbicides, except napropamide.

Typically, the instructions for use will instruct the user how to apply the first component (ie, napropamide or a composition containing napropamide) to the crop and monocot weed site along with the second herbicide. The second herbicide is usually contained in the third component (if present).

The examples below illustrate the invention. However, they do not limit the invention in any way. In particular, they can be used as a measure of the effectiveness and selectivity of the herbicide composition when applied to a crop growing area, and therefore a negative result for any particular method is not determinative.

Examples

A suspension concentrate (SC) containing 450 g/L napropamide-m (40.9 wt%) was prepared and applied to crops as described herein. Suspension concentrates of napropamide are commercially available under the trade name Devrinol (United Phosphorus).

Example 1.

A herbicidal composition consisting of SC containing 450 g/L napropamide-m was applied to winter wheat before or after emergence. Normalized plant number was determined as the percentage of the number of plants observed in the absence of the herbicide. Control experiments were performed using conventional Trooper herbicide as defined above. The amount and method of application of the compositions applied to the crop are shown in table. 1 below.

Table 1

Herbicide Applied quantity (l/ha) Method of application Napropamide-m, SC 450 g/l 0.40 before sunrise Napropamide-m, SC 450 g/l 0.70 before sunrise Napropamid-t, SC 450 g/l 1.00 before sunrise Napropamide-m, SC 450 g/l 1.40 before sunrise Napropamide-m, SC 450 g/l 1.70 before sunrise Napropamide-m, SC 450 g/l 0.70 immediately after germination Napropamide-m, SC 450 g/l 1.40 immediately after germination Napropamide-m, SC 450 g/l + Trooper 0.70 + 2.50 immediately after germination Napropamide-m, SC 450 g/l + Trooper 1.40 + 2.50 immediately after germination Trooper/Malibu 2.50 before sunrise Trooper 5.00 before sunrise Trooper 4.00 before sunrise Trooper 8.00 before sunrise

Results as the average of 6 field trials (napropamide; Trooper low dose: 4 plots; Trooper herbicide high dose: 2 plots) with herbicide applied in October are shown in FIG. 1. As can be seen, the application of napropamide did not have a noticeable effect on the growth of winter wheat. Plant survival after germination was 100% of the survival level in the absence of napropamide.

Similar experiments were carried out at another site, where the effect of seed depth was determined; see example 3 below. Control experiments were performed using conventional herbicides Trooper and Xerton as defined above.

The amount and method of application of the compositions applied to the crop are shown in table. 2 below.

- 12 043622

table 2

Herbicide Applied quantity (l/ha) Method of application Absent (the culture was not treated) Napropamide-m, SC 450 g/l 0.4 before sunrise

Napropamide-m, SC 450 g/l 0.7 before sunrise Napropamide-m, SC 450 g/l 1 before sunrise Napropamide-m, SC 450 g/l 1.4 before sunrise Napropamide-m, SC 450 g/l 1.7 before sunrise Trooper/Malibu 2.5 before sunrise Xerton 0.6 before sunrise

The results are shown in Fig. 2. As can be seen, the application of napropamide had a very weak effect on the growth of winter wheat. Plant survival after emergence was comparable to survival after application of conventional herbicides Trooper/Malibu and Xerton.

Example 2.

A herbicidal composition consisting of SC containing 450 g/l napropamide-m was applied to winter wheat before or after emergence (BBSN 11). The percentage of phytotoxicity was determined. Control experiments were performed using conventional Trooper herbicide as defined above. The amount and method of application of the compositions applied to the crop, and the results of application are shown in table. 3 below.

Table 3

Herbicide Applied quantity (l/ha) Method of application Phytotoxicity (%) 2 weeks 4 weeks 146 DAA 159 DAA Absent (the culture was not treated) - - Napropamide-m, SC 450 g/l 0.4 before sunrise 0.0 0.0 0 0 Napropamide-m, SC 450 g/l 0.7 before sunrise 0.0 0.0 0 0 Napropamide-m, SC 450 g/l 1 before sunrise 0.0 0.2 0 2

Napropamide-m, SC 450 g/l 1.4 before sunrise 0.1 1.4 0 4 Napropamide-m, SC 450 g/l 1.7 before sunrise 0.6 3.2 5 9 Napropamide-m, SC 450 g/l 0.7 VVSN 11 0.0 0.0 0 2 Napropamide-m, SC 450 g/l 1.4 VVSN and 0.0 0.0 0 6 Napropamide-m, SC 450 g/l + Trooper 0.7 + 2.5 VVSN 11 0.0 1.7 0 2 Napropamide-m, SC 450 g/l + Trooper 1.4 + 2.5 VVSN 11 0.0 1.9 0 4 Trooper/Malibu 2.5 or 4 before sunrise 0.1 1.0 0 6 Trooper 5 or 8.00 before sunrise 1.2 3.5 1 13

The results show that napropamide exhibits a low degree of phytotoxicity towards cereals such as wheat.

- 13 043622

Example 3.

Experiments were conducted to assess the influence of the depth at which crop seeds are planted. A herbicidal composition consisting of SC containing 450 g/L napropamide-m was applied by spraying to winter wheat before emergence. Normalized plant number was determined at 20 DAA as a percentage of the number of plants observed in the absence of herbicide. Control experiments were performed using conventional herbicides Trooper and Xerton as defined above. The number of compositions applied to the crop and the results of plant growth are shown in table. 4 below.

Table 4

Herbicide Applied quantity (l/ha) Planting depth (cm) 0.5 1 2 3 Absent (the culture was not treated) - 100 100 100 100 Napropamide-m, SC 450 g/l 0.4 78 90 97 100 Napropamid-t, SC 450 g/l 0.7 73 83 92 100 Napropamid-t, SC 450 g/l 1 60 75 92 98 Napropamid-t, SC 450 g/l 1.4 56 71 86 101 Napropamid-t, SC 450 g/l 1.7 50 72 90 99 Xerton 0.6 75 82 95 98 Malibu 2.5 70 83 98 100

The results show that napropamide is selective for winter wheat and is particularly useful at increased planting depth.

Example 4.

Experiments were conducted to evaluate the effect of increasing time (measured as days after anthesis, DAA) after application of a herbicide composition consisting of SC containing 450 g/L napropamide-m. The herbicide composition was applied by spraying in a test pot (planting depth 2 cm) to winter wheat before emergence. Normalized plant number was determined as the percentage of the number of plants observed in the absence of the herbicide.

Control experiments were performed using conventional herbicides Trooper and Xerton as defined above. The number of compositions applied to the crop and the resulting plant growth are shown in table. 5 below.

Table 5

Herbicide Applied quantity (l/ha) Plant growth And DAA 25DAA 54 DAA

Napropamide-m, SC 450 g/l 0.4 96 93 99 Napropamid-t, SC 450 g/l 0.7 92 94 99 Napropamid-t, SC 450 g/l 1 86 93 96 Napropamid-t, SC 450 g/l 1.4 87 92 99 Napropamid-t, SC 450 g/l 1.7 92 94 88 Xerton 0.6 81 83 69 Malibu 2.5 89 96 101

The results show that napropamide is selective for winter wheat and that all phytotoxic effects decrease over time. Compared to conventional herbicide Xerton, there is a significant reduction in phytotoxicity. Particularly favorable effects are observed when napropamide is applied in an amount of less than 1.7 l/ha, SC 450 g/l.

Example 5.

Experiments were conducted to evaluate the effect of increasing time (measured as days after anthesis, DAA) after application of a herbicide composition consisting of SC containing 450 g/L napropamide-m. The herbicide composition was applied by spraying in a test pot (planting depth 2 cm) to winter wheat before emergence. The percentage of phytotoxicity was determined. Control experiments were performed using conventional herbicides Trooper and Xerton as defined above. The number of compositions applied to the crop and the resulting phytotoxicity are shown in Table. 6 below.

- 14 043622

Table 6

Herbicide Applied quantity (l/ha) Phytotoxicity (%) And DAA 25DAA 54 DAA Napropamide-m, SC 450 g/l 0.4 1.5 0.0 0.0 Napropamid-t, SC 450 g/l 0.7 6.0 1.3 0.0 Napropamid-t, SC 450 g/l 1 18.3 8.8 0.0 Napropamid-t, SC 450 g/l 1.4 23.8 17.0 8.8 Napropamid-t, SC 450 g/l 1.7 23.8 16.8 15.0 Xerton 0.6 69.5 76.8 73.0 Malibu 2.5 9.0 7.5 0.0

The results show that napropamide is selective for winter wheat and that all phytotoxic effects decrease over time. Compared to conventional herbicide Xerton, there is a significant reduction in phytotoxicity.

Example 6.

Experiments were conducted to evaluate the effectiveness of herbicide compositions containing napropamide-m in controlling the common weed ALOMY (Alopecurus myosuroides lineage S), which is resistant to control by conventional herbicides such as Xerton. The percentage effectiveness of the herbicide composition was determined over time (measured as days after flowering, DAA) following application of a herbicide composition consisting of SC containing 450 g/L napropamide-m. The herbicide composition was applied by spraying in a test pot (planting depth 2 cm) to ALOMY (line S) before emergence. Control experiments were performed using conventional herbicides Trooper/Malibu and Xerton as defined above. The number of compositions applied to the weed and the resulting percentage of weed control are shown in Table 1. 7 below.

Table 7

Herbicide Applied quantity (l/ha) Efficiency (%) And DAA 25DAA 54 DAA Napropamide-m, SC 450 g/l 0.4 81.7 88.0 93.0 Napropamid-t, SC 450 g/l 0.7 85.4 89.7 91.3 Napropamid-t, SC 450 g/l 1 93.0 97.6 99.3 Napropamid-t, SC 450 g/l 1.4 96.7 99.3 98.3 Napropamid-t, SC 450 g/l 1.7 99.1 98.8 99.3 Xerton 0.6 49.3 48.6 50.2 Trooper/Malibu 2.5 90.6 96.4 96.6

The results show that napropamide is effective in controlling the growth of weeds such as ALOMY (S line). Napropamide is significantly more effective than conventional herbicides such as Xerton and can provide improved control compared to herbicides such as Trooper/Malibu at significantly lower application levels.

Example 7.

Experiments have been conducted to evaluate the effectiveness of herbicide compositions containing napropamide-m in controlling the common weed ALOMY (Alopecurus myosuroides lineage Peldon multi-R), which is resistant to control by conventional herbicides such as Xerton. The percentage effectiveness of the herbicide composition was determined over time (measured as days after flowering, DAA) following application of a herbicide composition consisting of SC containing 450 g/L napropamide-m. The herbicide composition was applied by spraying in a test pot (planting depth 2 cm) to ALOMY (Peldon multi-R line) before emergence. Control experiments were performed using conventional herbicides Trooper/Malibu and Xerton as defined above. The number of compositions applied to the weed and the resulting percentage of weed control are shown in Table 1. 8 below.

-

Claims (1)

Table 8 Herbicide Applied quantity (l/ha) Efficiency (%) And DAA 25DAA 54 DAA Napropamide-m, SC 450 g/l 0.4 66.3 74.5 78.9 Napropamid-t, SC 450 g/l 07 92.1 90.9 86.5 Napropamide-m, SC 450 g/l 1 91.6 90.9 94.0 Napropamide-m, SC 450 g/l 1.4 91.4 92.7 94.0 Napropamide-m, SC 450 g/l 1.7 100.0 100.0 100.0 Xerton 0.6 32.8 43.7 52.6 Trooper/Malibu 2.5 100.0 100.0 97.7 The results show that napropamide is effective in controlling the growth of weeds such as ALOMY (Peldon multi-R line). Napropamide is significantly more effective than conventional herbicides such as Xerton and can provide improved control compared to herbicides such as Trooper/Malibu and at significantly reduced application levels. Particularly beneficial effects are observed when napropamide is applied in an amount of more than 1 l/ha, SC 450 g/l. Example 8. Experiments were conducted to evaluate the effectiveness of herbicide compositions containing napropamide-m in controlling the common weed ALOMY (Alopecurus myosuroides) in a field trial. Weeds grew at a density of approx. 5-10 plants/ ^m2 . The percentage effectiveness of the herbicide composition was determined at 207 days after anthesis (DAA) after application of the herbicide composition consisting of SC containing 450 g/L napropamide-m. The herbicide composition was applied by spraying the weeds either before or after emergence (BBSN 11). Control experiments were performed using conventional Trooper herbicide as defined above. The number of compositions applied to the weed and the resulting percentage of weed control are shown in Table 1. 9 below. Table 9 Herbicide (g/ha) Herbicide Application Applied quantity (l/ha) Efficiency (%) Nap FFT PDM 207 DAA 108 Napropamide-m, SC 450 g/l Before sunrise 0.4 45 315 Napropamide-m, SC 450 g/l Before sunrise 0.7 50 450 Napropamide-m, SC 450 g/l Before sunrise 1 55 630 Napropamide-m, SC 450 g/l Before sunrise 1.4 68 765 Napropamide-m, SC 450 g/l Before sunrise 1.7 70 315 Napropamide-m, SC 450 g/l VVSN 11 0.7 58 630 Napropamide-m, SC 450 g/l VVSN 11 1.4 65 315 150 750 Napropamide-m, SC 450 g/l + Trooper VVSN 11 0.7 + 2.5 94 630 150 750 Napropamide-m, SC 450 g/l + Trooper VVSN 11 1.4 + 2.5 96 150 750 Trooper Before sunrise 2.5 90 300 1500 Trooper Before sunrise 5 98 Nap = napropamide-m FFT = flufenacet PDM = pendimethalin The results show that napropamide is effective in controlling the growth of weeds such as ALOMY and can be applied alongside conventional herbicides such as Trooper to improve weed control effectiveness. CLAIM 1. Use of napropamide for selective control of weeds on a site for growing grain crops; wherein the crop is present on the site or is planted on the site after application of said napropamide to the site, wherein said weed is resistant to control by ethophumesate, flufenacet and/or pendimethalin. -