BR112019023586B1 - 4-AMINO-6-(HETEROCYCLIC)PICOLINATES AND 6-AMINO-2-(HETEROCYCLIC) PYRIMIDINE-4-CARBOXYLATES AND THEIR USES AS HERBICIDES - Google Patents

Abstract

4-amino-6-(heterocyclic)picolinates and their derivatives; 6-amino-2-(heterocyclic) pyrimidine-4-carboxylates and derivatives thereof; and methods of using them as herbicides.

Description

CROSS REFERENCE TO RELATED ORDERS

[0001] This application claims the benefit of the North American provisional patent application serial number 62/504,148 filed on May 10, 2017, the entire disclosure of which is expressly incorporated herein by reference.

FIELD

[0002] The present disclosure includes herbicidal compounds, compositions containing the same and methods for controlling undesirable vegetation with said compounds and compositions.

BACKGROUND

[0003] The occurrence of undesirable vegetation, for example, weeds, is a constant problem faced by farmers in crops, pastures and other locations. Weeds compete with crops and negatively impact crop yields. The use of chemical herbicides is an important tool in controlling undesirable vegetation. Undesirable vegetation kochia and common poppy are particularly problematic in crop fields (e.g. wheat, barley, corn, oats, canola and sugar beet), pastures, roads, wastelands and ditches.

[0004] For example, Kochia (Kochia scoparia) is an early summer emergence annual species commonly found in the western United States and Canada. It is a herbaceous dicotyledon and a member of the Chenopodiaceae family. Kochia was introduced to North America from Europe as an ornamental due to its red color in late summer and fall. Kochia (Kochia scoparia (L.) Schrad.) is one of the most problematic annual broadleaf weeds in crop fields, pastures, roads, wastelands and ditches throughout the Northern Great Plains (NGP). . If not controlled early, kochia causes severe yield reductions (of up to 60%) in crops including wheat, barley, corn and sugar beet and can be the main weed problem in chemical cultivation.

[0005] Seeds have little to no dormancy and the majority (>90%) of seeds on or near the soil surface, in no-till conditions, germinate in early spring, with two to three emergency flushes during the summer. Kochia exhibits rapid growth and blooms in late summer. The weed is capable of self-pollination and cross-pollination and reproduces by seeds. A single kochia plant is capable of producing up to 50,000 seeds that can be dispersed by wind, water, contaminants in hay, farming equipment or by vehicles on the farm. At maturity, the plant breaks at the base of the stem and “falls” across the landscape with the prevailing wind, a unique and rapid mechanism for seed dispersal. Furthermore, kochia adapts well in drought, salt, and hot and cold conditions.

[0006] Herbicides that have been used in an attempt to control kochia include herbicides that inhibit acetolactate synthase (ALS), fluroxypyr, dicamba and glyphosate. Fluroxipyr and dicamba are selective herbicides that can control broadleaf weeds and typically do not harm grasses. (2-Dichlorophenoxy) acetic acid (2,4-D), which is often applied to control kochia, is not effective.

[0007] Glyphosate (such as Roundup®, a registered trademark of Monsanto Technology LLC, a Delaware limited liability company, or other similar generics) is a non-selective, broad-spectrum herbicide used for weed control. However, several factors related to the use of glyphosate for more than a decade for pre-plant weed control, in chemical cultivation, and for in-crop applications in Roundup Ready® crops (also a registered trademark of Monsanto Technology LLC), have resulted in the evolution of glyphosate-resistant weeds (currently 24 species in the United States), including kochia. For example, kochia biotypes resistant to triazines, auxins, ALS herbicides, and glyphosate have been well documented.

[0008] Corn poppy or common poppy (Papaver rhoeas) is one of the most problematic dicotyledonous weeds in winter cereals in areas of southern Europe that have a Mediterranean climate. Corn poppy is a competitive weed that is well known for its ability to reduce cereal yields. The ability of these species to invade, grow and remain in cereal fields can be attributed to the formation of a persistent seed bank, an extended period of germination and high seed production. Poppy management has become a serious and growing challenge for cereal farmers and authorities in Europe due to the spread of herbicide-resistant poppy biotypes. Populations of P. rhoeas resistant to sulfonylurea herbicides and/or auxin herbicides have been reported in Belgium, Denmark, France, Germany, Greece, Italy, Spain, Sweden and the United Kingdom. Some populations of P. rhoeas resistant to photosystem II (PSII) inhibition herbicides have been found in Poland. The spread of herbicide-resistant biotypes of P. rhoeas is a threat to the profitability of cereal production systems.

[0009] Therefore, there remains a need for new chemical herbicides that offer a broader spectrum of weed control, selectivity, minimal crop damage, storage stability, ease of handling, high activity against weeds, and/or means to address herbicide tolerance developed toward conventional herbicides.

SUMMARY

[0010] Compounds of Formula where -C3; R1 is C3-C12 alkynyl or C1-C3 alkyl substituted with CN; R2 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, amino , C1-C4 alkylamino, C2-C4 haloalkylamino, formyl, C1-C3 alkylcarbonyl, C1-C3 haloalkylcarbonyl, cyano or a group of formula -CR17=CR18-SiR19R20R21, wherein R17 is hydrogen, F, or Cl; R18 is hydrogen, F, Cl, C1-C4 alkyl, or C1-C4 haloalkyl; and R19, R20 and R21 are independently C1-C10 alkyl, C3-C6 cycloalkyl, phenyl, substituted phenyl, C1-C10 alkoxy, or OH; R3 and R4 are independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, formyl, C1-C3 alkylcarbonyl, C1C3 haloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-alkylcarbamyl C6, C1-C6 alkylsulfonyl, C1-C6 trialkylsilyl, C1-C6 dialkylphosphonyl, or R3 and R4 taken together with N is a saturated 5- or 6-membered ring, or R3 and R4 taken together represent =CR3'(R4' ), wherein R3' and R4' are independently hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy or C1-C6 alkylamino, or, R3' and R4' taken together with =C represent a 5- or 6-membered saturated ring; R5 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, cycloalkyl, halocycloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1-C3 haloalkylthio, amino, C1-C4 alkylamino, C2-C4 haloalkylamino, OH or CN; R6 and R6' are independently hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, halocyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1C3 alkoxy, C1-C3 haloalkoxy, C1-alkylthio C3, C1-C3 haloalkylthio, amino, C1-C4 alkylamino or C2-C4 haloalkylamino, OH, CN, or NO2; R7 and R7' are independently hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, halocyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1C3 alkoxy, C1-C3 haloalkoxy, C1-alkylthio C3, C1-C3 haloalkylthio, amino, C1-C4 alkylamino, C2-C4 haloalkylamino, or phenyl; R8 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, formyl, C1-C6 alkylcarbonyl, C1-C6 cycloalkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxycarbonyl or an N-oxide thereof.

[0011] Methods for controlling undesirable vegetation are also provided including providing the compound of Formula (I) and (a) contacting the undesirable vegetation or area adjacent to the undesirable vegetation or (b) pre-contacting the undesirable vegetation. -emergency, with soil or water, a herbicidally effective amount of at least one compound of Formula (I) or agriculturally acceptable derivative thereof.

DETAILED DESCRIPTION I. Definitions

[0012] As used herein, herbicide and herbicide active ingredient can be understood to include a compound that controls undesirable vegetation when applied in an adequate amount.

[0013] As used herein, controlling or controlling undesirable vegetation means killing or avoiding vegetation, or causing some other adversity, modifying the effect of vegetation, e.g., deviation from natural growth or development, regulation, desiccation, delay and the like.

[0014] As used herein, a herbicidally effective or vegetation control amount can be understood to include the application of an amount of herbicidal active ingredient which controls the relevant undesirable vegetation.

[0015] As used herein, the application of a herbicide or herbicidal composition can be understood to include distributing it directly to the target vegetation or to the location thereof or to the area in which control of unwanted vegetation is desired. Examples of application methods include, but are not limited to, pre-emergency soil or water contact, post-emergence contact of undesirable vegetation or area adjacent to undesirable vegetation.

[0016] As used herein, plants and vegetation may include, but are not limited to, dormant seeds, germinating seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation and established vegetation.

[0017] As used herein, immature vegetation can be understood to include small vegetative plants before the reproductive stage, and mature vegetation refers to vegetative plants during and after the reproductive stage.

[0018] As used herein, unless otherwise specified, acyl refers to formyl, C1-C3 alkylcarbonyl, and C1-C3 haloalkylcarbonyl. C1-C6 acyl refers to formyl, C1-C5 alkylcarbonyl, and C1-C5 haloalkylcarbonyl (the group contains a total of 1 to 6 carbon atoms).

[0019] As used herein, alkyl refers to saturated, straight-chain or branched-chain hydrocarbon moieties. Unless otherwise specified, C1-C10 alkyl groups are intended. Examples include methyl, ethyl, propyl, 1-methyl-ethyl, butyl, 1-methyl-propyl, 2-methyl-propyl, 1,1-dimethyl-ethyl, pentyl, 1-methyl-butyl, 2-methyl-butyl, 3-methyl-butyl, 2,2-dimethyl-propyl, 1-ethyl-propyl, hexyl, 1,1-dimethyl-propyl, 1,2-dimethyl-propyl, 1-methyl-pentyl, 2-methyl-pentyl, 3-methyl-pentyl, 4-methyl-pentyl, 1,1-dimethyl-butyl, 1,2-dimethyl-butyl, 1,3-dimethyl-butyl, 2,2-dimethyl-butyl, 2,3-dimethyl- butyl, 3,3-dimethyl-butyl, 1-ethyl-butyl, 2-ethyl-butyl, 1,1,2-trimethyl-propyl, 1,2,2-trimethyl-propyl, 1-ethyl-1-methyl- propyl, and 1-ethyl-2-methyl-propyl.

[0020] As used herein, haloalkyl refers to straight-chain or branched-chain alkyl groups, in which, in these groups, hydrogen atoms can be partially or completely replaced by halogen atoms. Unless otherwise specified, groups C1-C8 are intended. Examples include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, and 1,1,1-trifluoroprop-2-yl .

[0021] As used herein, alkenyl refers to unsaturated hydrocarbon moieties, straight or branched chain, containing a double bond. Unless otherwise specified, C2-C8 alkenyl are intended. Alkenyl groups may contain more than one unsaturated bond. Examples include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2- hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl- 2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3- pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2- butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1- butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2- butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1- ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl- 2-propenyl, 1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl. Vinyl refers to a group having the structure -CH=CH2; 1- propenyl refers to a group with the structure -CH=CH-CH3; and 2-propenyl refers to a group with the structure -CH2-CH=CH2.

[0022] As used herein, alkynyl represents straight or branched chain hydrocarbon moieties containing a triple bond. Unless otherwise specified, C2-C8 alkynyl groups are intended. Alkynyl groups may contain more than one unsaturated bond. Examples include C2-C6 alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl , 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl , 1-ethyl-2-propynyl, 1-hexinyl, 2-hexinyl, 3-hexinyl, 4-hexinyl, 5-hexinyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2 -pentynyl, 4-methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl , 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl , 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl.

[0023] As used herein, alkoxy refers to a group of formula R-O-, where R is alkyl as defined above. Unless otherwise specified, alkoxy groups wherein R is a C1-C8 alkyl group are intended. Examples include methoxy, ethoxy, propoxy, 1-methyl-ethoxy, butoxy, 1-methyl-propoxy, 2-methyl-propoxy, 1,1-dimethyl-ethoxy, pentoxy, 1-methyl-butyloxy, 2-methyl-butoxy, 3-methyl-butoxy, 2,2-dimethyl-propoxy, 1-ethyl-propoxy, hexoxy, 1,1-dimethyl-propoxy, 1,2-dimethyl-propoxy, 1-methyl-pentoxy, 2-methyl-pentoxy, 3-methyl-pentoxy, 4-methyl-pentoxy, 1,1-dimethyl-butoxy, 1,2-dimethyl-butoxy, 1,3-dimethyl-butoxy, 2,2-dimethyl-butoxy, 2,3-dimethyl- butoxy, 3,3-dimethyl-butoxy, 1-ethyl-butoxy, 2-ethyl-butoxy, 1,1,2-trimethyl-propoxy, 1,2,2-trimethyl-propoxy, 1-ethyl-1-methyl- propoxy and 1-ethyl-2-methyl-propoxy.

[0024] As used herein, haloalkoxy refers to a group of formula R-O-, where R is haloalkyl as defined above. Unless otherwise specified, haloalkoxy groups wherein R is a C1-C8 alkyl group are intended. Examples include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluormethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluorethoxy, 2-fluorethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, and 1,1,1-trifluoroprop-2 -oxy.

[0025] As used herein, alkylthio refers to a group of formula R-S- where R is alkyl as defined above. Unless otherwise specified, alkylthio groups wherein R is a C1-C8 alkyl group are intended. Examples include methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1- ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio, and 1-ethyl-2-methylpropylthio.

[0026] As used herein, haloalkylthio refers to an alkylthio group as defined above in which the carbon atoms are partially or fully replaced with halogen atoms. Unless otherwise specified, haloalkylthio groups wherein R is a C1-C8 alkyl group are intended. Examples include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2- trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and 1,1,1-trifluoroprop-2- iltio.

[0027] As used herein, aryl, as well as derivative terms such as aryloxy, refers to a phenyl, indanyl or naphthyl group with phenyl being preferred. The term heteroaryl, as well as derivative terms such as heteroaryloxy, refers to 5- or 6-membered aromatic rings containing one or more heteroatoms, namely, N, O or S; these aromatic and heteroaromatic rings may be fused to other aromatic and/or heteroaromatic systems. The aryl or heteroaryl substituents may be unsubstituted or substituted with one or more substituents selected from halogen, hydroxy, nitro, cyano, formyl, C1C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkyl , C1-C6 haloalkoxy, C1-C6 acyl, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkoxycarbonyl, C1-C6 carbamoyl, hydroxycarbonyl, C1C6 alkylcarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl, C1 dialkylaminocarbonyl -C6, as long as the substituents are sterically compatible and the chemical bonding and energy stress rules are satisfied. Preferred substituents include halogen, C1-C2 alkyl and C1C2 haloalkyl.

[0028] As used herein, alkylcarbonyl refers to an alkyl group linked to a carbonyl group. C1-C3 alkylcarbonyl and C1-C3 haloalkylcarbonyl refer to groups in which a C1-C3 alkyl group is attached to a carbonyl group (the group contains a total of 2 to 4 carbon atoms).

[0029] As used herein, alkoxycarbonyl refers to O a group of formula OR where R is alkyl.

[0030] As used herein, arylalkyl refers to an alkyl group substituted with an aryl group. Arylalkyl C7C10 refers to a group in which the total number of carbon atoms in the group is 7 to 10.

[0031] As used herein, alkylamino refers to an amino group substituted with one or two alkyl groups, which may be the same or different.

[0032] As used herein, haloalkylamino refers to an alkylamino group in which the alkyl carbon atoms are partially or fully replaced with halogen atoms.

[0033] As used herein, C1-C6 alkylaminocarbonyl refers to a group of formula RNHC(O)- in which R is C1-C6 alkyl, and C1-C6 dialkylaminocarbonyl refers to a group of formula R2NC(O)- in that each R is independently C1C6 alkyl.

[0034] As used herein, alkylcarbamyl refers to a carbamyl group substituted on a nitrogen with an alkyl group.

[0035] As used herein, alkylsulfonyl refers to O II S SR a group of formula , where R is alkyl. O

[0036] As used herein, carbamyl (also referred to as carbamoyl and aminocarbonyl) refers to a group of formula O .

[0037] As used herein, dialkylphosphonyl refers to a group of formula where R is independently OR alkyl in each occurrence.

[0038] As used herein, C1-C6 trialkylsilyl refers to a group of formula -SiR3 in which each R is independently a C1-C6 alkyl group (the group contains a total of 3 to 18 carbon atoms).

[0039] As used herein, Me refers to a methyl group; OMe refers to a methoxy group; i-Pr refers to an isopropyl group.

[0040] As used herein, the term halogen including derivative terms such as halo refers to fluorine, chlorine, bromine and iodine.

[0041] As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity or that are or can be converted in plants, water or soil to the referenced herbicide. Examples of agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized or otherwise converted, for example in plants, water or soil, to the corresponding carboxylic acid, which, depending on pH, can be in dissociated or non-dissociated form.

[0042] Examples of esters include those derived from C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 alkyl alcohols substituted with aryl, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol, substituted or unsubstituted butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or benzyl alcohols. Benzyl alcohols can be substituted with 1 - 3 substituents independently selected from halogen, C1-C4 alkyl or C1-C4 alkoxy. Esters can be prepared by coupling the acids with the alcohol using any number of suitable activating agents such as those used for coupling peptides, such as dicyclohexyl carbodiimide (DCC) or carbonyl diimidazole (CDI); by reacting the acids with alkylating agents such as substituted or unsubstituted alkyl halides, substituted or unsubstituted alkynyl halides, substituted or unsubstituted cyanoalkyl halides (e.g., cyanomethyl acetate, such as cyanomethyl 2-bromoacetate)) or substituted or unsubstituted alkylsulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the corresponding acid chloride of an acid with a suitable alcohol; by reacting the corresponding acid with a suitable alcohol in the presence of an acid catalyst or by transesterification.

[0043] Compounds of Formula (I) include N-oxides. Pyridine N-oxides can be obtained by oxidizing the corresponding pyridines. Suitable oxidation methods are described, for example, in Houben-Weyl, Methoden der organischen Chemie [Methods in organic chemistry], expanded and subsequent volumes for the 4th edition, volume E 7b, p. 565 f.

II. Compounds

[0044] The compounds described here are compounds of Formula (I): where ; R1 is C3-C12 alkynyl or C1-C3 alkyl substituted with CN; R2 is halogen, C1-C4 alkyl, C1-C4 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, amino , C1-C4 alkylamino, C2-C4 haloalkylamino, formyl, C1-C3 alkylcarbonyl, C1-C3 haloalkylcarbonyl, cyano or a group of formula -CR17=CR18-SiR19R20R21, wherein R17 is hydrogen, F or Cl; R18 is hydrogen, F, Cl, C1-C4 alkyl or C1C4 haloalkyl; and R19, R20 and R21 are independently C1-C10 alkyl, C3-C6 cycloalkyl, phenyl, substituted phenyl, C1-C10 alkoxy, or OH; R3 and R4 are independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, formyl, C1-C3 alkylcarbonyl, C1C3 haloalkylcarbonyl, C1-C6 alkoxycarbonyl, C1-alkylcarbamyl C6, C1-C6 alkylsulfonyl, C1-C6 trialkylsilyl, C1-C6 dialkylphosphonyl or R3 and R4, taken together with N, are a 5- or 6-membered saturated ring or R3 and R4, taken together, represent =CR3'( R4'), wherein R3' and R4' are independently hydrogen, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy or C1-C6 alkylamino, or, R3' and R4', taken together with =C, they represent a 5- or 6-membered saturated ring; R5 is hydrogen, halogen, C1-C4 alkyl, C1C4 haloalkyl, cyclopropyl, halocyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1-C3 alkoxy, C1-C3 haloalkoxy, C1-C3 alkylthio, C1 haloalkylthio -C3, amino, C1-C4 alkylamino, C2-C4 haloalkylamino, OH or CN; R6 and R6' are independently hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, halocyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1C3 alkoxy, C1-C3 haloalkoxy, alkylthio C1-C3, C1-C3 haloalkylthio, amino, C1-C4 alkylamino or C2-C4 haloalkylamino, OH, CN or NO2; R7 and R7' are independently hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, cyclopropyl, halocyclopropyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C1C3 alkoxy, C1-C3 haloalkoxy, alkylthio C1-C3, C1-C3 haloalkylthio, amino, C1-C4 alkylamino, C2-C4 haloalkylamino or phenyl; R8 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, formyl, C1-C6 alkylcarbonyl, C1-C6 cycloalkylcarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxycarbonyl , C1-C6 haloalkoxycarbonyl, arylcarbonyl, heteroarylcarbonyl, C1-C6 alkylcarbamyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, arylsulfonyl, C1-C6 trialkylsilyl, amino, C1-C4 alkylamino, cyano or phenyl.

[0045] In some embodiments, the compound of Formula (I) is wherein X is N, CH, CF, CCl or CBr; R1 is C3-C12 alkynyl or C1-C3 alkyl substituted with CN; R2 is chlorine; R3 and R4 are hydrogen; R5 is hydrogen, halogen, OH, amino, CN, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylamino, or cyclopropyl; R6 and R6 'are independently hydrogen, halogen, OH, NH2, CN, C1-C3 alkyl, C1-C3 alkoxy, cyclopropyl or vinyl; R7 and R7 ' are independently hydrogen, halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 alkylthio, cyclopropyl, C1-C3 alkylamino, or phenyl; and R8 is hydrogen, C1-C6 alkylcarbonyl, C1-C6 cycloalkylcarbonyl, C1-C6 alkoxycarbonyl, or arylcarbonyl; or an N-oxide or an agriculturally acceptable salt thereof.

[0046] In some embodiments, the compound of Formula (I) is wherein R2 is halogen, C2-C4 alkenyl, C2-C4 haloalkenyl, or C1-C4 alkoxy; R5 is hydrogen or F; R6 is hydrogen or F; R6' is hydrogen; and independently, hydrogen or halogen.

[0047] In some embodiments (I) is wherein R2 is chlorine, methoxy, vinyl, or 1-propenyl; R3 and R4 are hydrogen; and X is CF.

[0048] In some embodiments: R1 is propargyl; and the compound of Formula (I) is

[0049] In some embodiments: R1 is cyanomethyl; the compound of Formula (I) is

III. Preparation Methods

[0050] Procedures for synthesizing 4-amino-6-(heterocyclic)picolinic acids, where X is CH or CF and R1 is H, and 6-amino-2-(heterocyclic)pyrimidine carboxylic acids, where X is N and R1 and H are described in U.S. Patent No. 9,637,505 by Eckelbarger et al., which is incorporated herein by reference in its entirety.

[0051] A procedure for synthesizing compounds of Formula (I) in which R1, R2, R3, R4, R5, R6, R6', R7, R7' and R8 are as defined above is shown in Scheme 1

[0052] Acids 1-1 can be converted to compounds of Formula (I) by esterification (Scheme 1, step a). Esters can be prepared by coupling the acids with an alcohol using any number of suitable activating agents such as those used for coupling peptides including dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by reacting the acids with alkylating agents such as substituted or unsubstituted alkyl halides, substituted or unsubstituted alkynyl halides, substituted or unsubstituted cyanoalkynyl halides or substituted or unsubstituted alkyl sulfonates in the presence of a base such as triethylamine or lithium carbonate or potassium; by reacting the corresponding acid chloride of an acid with a suitable alcohol; or by reacting the corresponding acid with a suitable alcohol in the presence of an acid catalyst. Reactions can be carried out in polar, aprotic solvents such as dimethyl sulfoxide, N,N-dimethylformamide, dichloromethane or 1,2-dichloroethane.

IV. Mixtures

[0053] In some embodiments, the compounds, compositions and methods provided herein are used in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the compounds described herein can be formulated with another herbicide or herbicides, batch mixed with another herbicide or herbicides, or applied sequentially to the other herbicide or herbicides. Some of the herbicides that may be employed in conjunction with the compounds of the present disclosure include, but are not limited to, 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D esters and amines; 2,4-DB; 3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, alidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametrine, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, methyl amiprophos, amitrol, ammonium sulfamate, anilophos, anisuron, asulam, atraton, atrazine, azafenidine, azimsulfuron, aziprothrin, barbana, BCPC, beflubutamide, benazoline, bencarbazone, benfluralin, benfuresate, methyl bensulfurone, bensulide, bentiocarb, bentazone sodium salt, benzadox, benzfendizone, benzipram, benzobicyclone, benzofenap, benzofluorine, benzoylprop , benzthiazuron , biciclopyrone, bifenox, bilanafos, bispiribac sodium salt, borax, bromacil, bromobonil, bromobutide, bromophenoxim, bromoxynil, brompirazone, butachlor, butafenacil, butamifos, butenachlor, butidazole, butyuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrol, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole, carfentrazone-ethyl, CDEA, CEPC, clomethoxyfen, chlorambene, chloranocril, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazol, chlorflurenol, cloridazon, clorimuron, chlornitrophen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorprocarb, chlorprofam, chlorsulfuron, chlortal, chlorthiamide, cinidon-ethyl, cinmethylline, cinosulfuron, cisanilide, clacyfos, cletodim, cliodinate, clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop, cloproxidim, clopyralid, cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumiluron, cyanatrine, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxidim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, ciprazole, cypromide, daimuron, dalapon, dazomet, delachlor, desmedifam, desmetrin, dialate, dicamba, diclobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop, diclosulam, dietmquat, diethyl, diphenopentene, difenoxuron, diffenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethchlor, dimethethrin, dimethenamid, dimethenamid-P, dimexane, dimidazon, dinitramine, dinophenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamide, dipropetrin, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, - P-ethyl, fenoxaprop-P-ethyl + isoxadifen-ethyl, fenoxasulfone, phenquinotrione, fenteracol, fentiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, florpyrauxifene-benzyl, fluazifop, fluazifop-P-butyl , fluazolate, flucarbazone, fluketosulfuron, fluchloralin, flufenacet, flufenican, flufenpir-ethyl, flumetsulam, flumezin, flumiclorac-pentyl, flumioxazine, flumipropin, fluometurone, fluordifen, fluorglycofen, fluormidine, fluornitrophen, fluothiiuron, flupoxam, flupropacil, flupropanate, flupirsulfuron, flurid one , flurochloridone, fluroxypyr, flurtamon, flutiacet, falesafen, foramsulfuron, fosamine, furyloxifen, glufosinate, ammonium glufosinate, glyphosate, halosafen, halosulfuron-methyl, haloxidine, haloxyfop-methyl, haloxyfop-P-methyl, halauxifen-methyl, hexachloroacetone, hexaflurate , hexazinone, imazametabenz, imazamox, imazapic, imazapyr, imazaquin, imazetapyr, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprimidam, isocarbamide, isocyl, isomethiozine, is onoruron, isopolinate, isopropaline, isoproturon , isouron, isoxaben, isoxachlortol, isoxaflutol, isoxapirifop, karbutylate, ketospiradox, lactofen, lancotrione, lenacil, linuron, MAA, MAMA, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide , mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, metabenzthiazuron, metalpropaline, methazol, methiobencarb, methiozolin, methiuron, metometon, metoprothrin, methyl bromide, methyl isothiocyanate, methyldimron, metobenzuron, metobromuron, metolaclo ro, metosulam , methoxuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morphamquat, MSMA, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, nipiraclofen, nitralin, nitrophen, nitrofluorfen, norflurazon, noruron , OCH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapirazon, oxasulfuron, oxaziclomephone, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perflu ideal, petoxamide, phenisofam, phenmedifam, phenmedifam-ethyl, phenobenzuron, phenyl mercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretylachlor, primisulfuron-methyl, procyazine, prodiamine, profluazole, profluralin , profoxidim, proglinazine, prohexadione-calcium, prometon, promethrin, propachlor, propanil, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propysulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prinachlor, pidanon, pyraclonil, pyraflufen, pyrasulfotol, p irazogil , pyrazolinate, pyrazosulfuron-etil, pyrazoxiphene, pyribenzoxim, pi-pi-piriclor, pyridafol, pyridate, piriftalid, piriminobac, pyrinisulfan, pyrxasulfone, piroxsulam, kinclorac, quinamerac, quinoclamine, quinonamid, quizalofop, quizalofop, quizalofop, quizalofop, quizalofop P- P--Ethyl, Rodetanil , rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simethrin, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, acid Sulfuric, sulglycapin, swep, TCA, tebutam, tebutiuron, tefuriltriona, tempraloxidim, terbacil, terbucarb, tebucloro, tebumeton, tebutylazine, tebutrin, tetrafluron, tenillcloro, thiazafluron, tidiazimin, tiencharon, tiencharon, tiencha Bazona-methyl, tifensulfuron, tiobencarb, thiafenacil, thiocarbazil, thioclorim, tolpiralate, topramezone, tralkoxidim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, tricamba, triclopyr esters and amines, tridiphane, triethazine, trifloxysulfuron, trifludimoxazine, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trime turon, tripropindan, tritac, tritosulfuron, vernolate and xylachlor. The mixing partner(s) may be formulated as a free acid or base or as a salt or ester, as defined above.

[0054] The compounds and compositions described herein can, in general, be employed in combination with known herbicide protection agents, such as benoxacor, benthiocarb, brassinolide, cloquintocet (e.g., mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazol-ethyl, fenclorim, flurazol, fluxfenim, furilazole, harpin proteins, isoxadifen-ethyl, mefenpyr-diethyl, 2-dichloromethyl 2-methyl 1,3-dioxolane also known as MG 191, dichloroacetyl- 1-oxa- 4-azaspiro(4,5)-decane also known as MON 4660, naphthalic anhydride (NA), oxabetrinyl, (R,S)-3-dichloroacetyl- 2,2,5-trimethyloxazolidine also known as R-29148, metcamifen, N-phenylsulfonyl benzoic acid amides or mixtures thereof, to improve their selectivity.

[0055] In some embodiments, the compounds provided herein can be employed in mixtures containing a herbicidally effective amount of the compound together with at least one agriculturally acceptable adjuvant or carrier. Examples of adjuvants or carriers include those that are not phytotoxic or significantly phytotoxic to valuable crops, for example, in the concentrations employed in the application of compositions for the selective control of weeds in the presence of crops, and/or do not react or react chemically, in significantly, with the compounds provided herein or other ingredients of the composition. Such mixtures may be designed for application directly to weeds or their sites or may be concentrates or formulations that are diluted with additional carriers and adjuvants prior to application. They may be solids, such as, for example, powders, granules, water-dispersible granules or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be supplied as a pre-mix or batch mixed.

[0056] Agronomically acceptable adjuvants and carriers that are useful in preparing the herbicide mixtures of the disclosure are well known to one skilled in the art. Some of these adjuvants include, but are not limited to, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; mixture of petroleum hydrocarbons, alkyl esters, organic acid and anionic surfactant; C9-C11 alkylpolyglucoside; phosphate alcohol ethoxylate; natural primary alcohol ethoxylate (C12-C16); di-sec-butylphenol EO - PO block copolymer; polysiloxane ethoxylate - methyl cap; nonylphenol + urea ammonium nitrate; methylated emulsified seed oil; tridecyl alcohol ethoxylate (8 EO) (synthetic); tallow amine ethoxylate (15 EO); PEG(400)dioleate-99.

[0057] Liquid carriers that can be used include water and organic solvents. Examples of organic solvents include, but are not limited to, petroleum or hydrocarbon fractions such as mineral oil, aromatic solvents, paraffinic oils and the like; 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; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric or other lower polyalcohols (containing 4-6 hydroxyls), such as 2-ethylhexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, adipate di-butyl, di-octyl phthalate and the like; esters of mono-, di- and poly-carboxylic acids and the like. Specific organic solvents include toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, N-methyl 2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers, and the like. In some embodiments, water is the carrier for diluting the concentrates.

[0058] Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, diatomite, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cotton seed hulls , wheat flour, soy flour, pumice, wood flour, walnut shell flour, lignin and the like. Suitable solid carriers may also include combinations of the solid carriers mentioned above.

[0059] In some embodiments, one or more surface active agents are used in the compositions of the present disclosure. Such surface active agents are, in some embodiments, employed in both solid and liquid compositions, for example, those designed to be diluted with carrier before application. Surface active agents may be anionic, cationic or nonionic in character and may be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Surfactants conventionally used in the art in formulation and which may be used in the present formulations are described, inter alia, in McCutcheon Detergents and Emulsifiers Annuals, MC Publishing Corp., Ridgewood, New Jersey, 1998, and in the Encyclopedia of Surfactants, volume I - III, Chemical Publishing Co., New York, 1980 - 81. Typical surface active agents include alkyl sulfate salts, such as diethanolammonium lauryl sulfate; alkylaryl sulfonate salts, such as calcium dodecylbenzene sulfonate; alkylphenol - alkylene oxide addition products such as nonylphenol ethoxylate - C18; alcohol addition products - alkylene oxide, such as alcohol tridecyl ethoxylate - C16; soaps, such as sodium stearate; alkyl naphthalene sulfonate salts, such as sodium dibutyl naphthalene sulfonate; salts of sulfosuccinate dialkyl esters, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethyl ammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono- and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed/canola oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cottonseed oil, linseed oil, oil palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, for example methyl esters.

[0060] Often, some of these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.

[0061] Other adjuvants commonly used in agricultural compositions include compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, blowing agents, penetration aids, adhering agents, dispersing agents, thickening agents, melting point depressants, antimicrobial agents and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulators, fungicides, insecticides and the like, and may be formulated with liquid or solid fertilizers, particulate fertilizer carriers, such as ammonium nitrate, urea and the like.

[0062] The concentration of active ingredients in the herbicidal compositions of this disclosure is, in general, from about 0.001 to about 98 weight percent. Concentrations of about 0.01 to about 90 weight percent are often employed. In compositions designed to be employed as concentrates, the active ingredients are generally present in a concentration of about 5 to about 98 weight percent, preferably about 10 to about 90 weight percent. Such compositions are typically diluted with an inert carrier, such as water, prior to application. Diluted compositions usually applied to weeds or weed sites generally contain about 0.0001 to about 1 weight percent active ingredient and preferably contain about 0.001 to about 0.05 weight percent.

[0063] As used herein, the modifier “about” used in connection with a quantity is inclusive of the indicated value and has the meaning dictated by the context (e.g., it includes at least the degree of error associated with the measurement of the particular quantity). . When used in the context of a range, the “about” modifier should also be considered as disclosing the range defined by the absolute values of the two endpoints. For example, the range “from about 2 to about 4” also discloses the range “from 2 to 4.”

V. Application Methods

[0064] The present compositions can be applied to weeds or their site by the use of conventional dusters, sprayers and granule applicators, powder or aerial, in addition to irrigation or flood water, and by other conventional means known to those skilled in the art. subject.

[0065] In some embodiments, the present compounds and compositions described herein are applied as a post-emergency application, pre-emergency application, water application to flooded paddy rice or bodies of water (e.g., ponds, lakes and streams ), or burning application.

[0066] In some embodiments, the compounds and compositions provided herein are used to control weeds in crops, including but not limited to citrus, apples, rubber, palm oil, forestry, direct seeding, water seeding and transplanted rice, wheat , barley, oats, rye, sorghum, corn, pastures, grasslands, mountainous areas, fallow, peatland, tree and vine orchards, aquatic or row crops, as well as non-crop settings, e.g. industrial vegetation management or rights of ticket. In some embodiments, the compounds and compositions are used to control woody plants, weeds, or broad-leaved sedges or grasses.

[0067] In some embodiments, the compounds and compositions provided here are used to control undesirable vegetation in rice. In certain embodiments, the undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash (broadleaf grass, BRAPP), Digitaria sanguinalis (L.) Scop. (digitated million, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (cock's foot millet, ECHCG), Echinochloa colonum (L.) LINK (colony grass, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (barnyard grass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (rice millet, ECHPH), Ischaemum rugosum Salisb. (male grass, ISCRU), Leptochloa chinensis (L.) Nees (red sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (leptocloa, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon Leptocloa, LEFPA), Panicum dichotomiflorum (L.) Michx. (panicum, PANDI), Paspalum dilatatum Poir. (longgrass, PASDI), Cyperus difformis L. (negrinha, CYPDI), Cyperus esculentus L. (sedge, CYPES), Cyperus would L. (sedge, CYPIR), Cyperus rotundus L. (sedge, CYPRO), species of Eleocharis (ELOSS), Fimbristylis miliacea (L.) Vahl (false cumin, FIMMI), Schoenoplectus juncoides Roxb. (jonquil, SPCJU), Schoenoplectus maritimus L. (sea jonquil, SCPMA), Schoenoplectus mucronatus L. (rice jonquil, SCPMU), species of Aeschynomene, (cork, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (alligator weed, ALRPH), Alisma plantago-aquatica L. (mule ear, ALSPA), Amaranthus species (purple pigweed and amaranth, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Eclipta alba (L.) Hassk. (button herb, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (water hyacinth, HETLI), Heteranthera reniformis R. & P. (new rice herbs, HETRE), Ipomoea hederacea (L.) Jacq. (morning glory, IPOHE), Lindernia dubia (L.) Pennell (dragon agave, LIDDU), Monochoria korsakowii Regel & Maack (monochory, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochory, MOOVA) , Murdannia nudiflora (L.) Brenan (trapoeraba, MUDNU), Polygonum pensylvanicum L., (Pennsylvania herb, POLPY), Polygonum persicaria L. (peach herb, POLPE), Polygonum hydropiperoides Michx. (bug weed, POLHP), Rotala indica (Willd.) Koehne (round-leaf rotala, ROTIN), Sagittaria species (bayonet, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (Colorado River hemp, SEBEX) or Sphenoclea zeylanica Gaertn. (sphenoclea, SPDZE).

[0068] In some embodiments, the compounds and compositions provided here are used to control undesirable vegetation in cereals. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (foxtail, ALOMY), Apera spica-venti (L.) Beauv. (apera, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (headwort, PHAMI), Poa annua L. (dog's hair, POAAN), Setaria pumila (Poir.) Roemer & J.A. Schultes (yellow foxtail grass, SETLU), Setaria viridis (L.) Beauv. (green foxtail grass, SETVI), Cirsium arvense (L.) Scop. (vine thistle, CIRAR), Galium aparine L. (pagamaco, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (wild mint, LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineapple weed, MATMT), Papaver rhoeas L. (poppy common, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Stellaria media (L.) Vill. (common chickweed, STEME), Veronica persica Poir. (Persian veronica, VERPE), Viola arvensis Murr. (field violet, VIOAR) or Viola tricolor L. (wild violet, VIOTR).

[0069] In some embodiments, the compounds and compositions provided here are used to control undesirable vegetation in strips and pastures. In certain embodiments, the undesirable vegetation is Ambrosia artemisiifolia L. (artemísia americana, AMBEL), Cassia obtusifolia (mata pasto, CASOB), Centaurea maculosa auct. non Lam. (evil flower, CENMA), Cirsium arvense (L.) Scop. (vine thistle, CIRAR), Convolvulus arvensis L. (bluebell, CONAR), Euphorbia esula L. (esula redonda, EPHES), Lactuca serriola L. / Torn. (wild lettuce, LACSE), Plantago lanceolata L. (sheep's tongue, PLALA), Rumex obtusifolius L. (butter plant, RUMOB), Sida spinosa L. (black broom, SIDSP), Sinapis arvensis L. (wild mustard, SINAR) , Sonchus arvensis L. (milkweed, SONAR), Solidago species (tango, SOOSS), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).

[0070] In some embodiments, the compounds and compositions provided here are used to control undesirable vegetation found in row crops. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (foxtail, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria platyphylla (Groseb.) Nash (broadleaf grass, BRAPP), Digitaria sanguinalis (L.) Scop. (digitated million, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (cocksfoot millet, ECHCG), Echinochloa colonum (L.) Link (colony grass, ECHCO), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (Banhado grass, PANDI), Panicum miliaceum L. (red millet, PANMI), Setaria faberi Herrm. (giant foxtail grass, SETFA), Setaria viridis (L.) Beauv. (green foxtail grass, SETVI), Sorghum halepense (L.) Pers. (barley grass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (sorghum, SORVU), Cyperus esculentus L. (sedge, CYPES), Cyperus rotundus L. (sedge, CYPRO), Abutilon theophrasti Medik. (Chinese jute malvão, ABUTH), species of Amaranthus (purple pigweed and amaranth, AMASS), Ambrosia artemisiifolia L. (American mugwort, AMBEL), Ambrosia psilostachya DC. (western sagebrush, AMBPS), Ambrosia trifida L. (giant sagebrush, AMBTR), Asclepias syriaca L. (wild cotton, ASCSY), Chenopodium album L. (common sagebrush, CHEAL), Cirsium arvense (L.) Scop. (vine thistle, CIRAR), Commelina benghalensis L. (erva de santa luzia, COMBE), Datura stramonium L. (trumpet, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Erigeron bonariensis L. (aboadeira, ERIBO), Erigeron canadensis L. (erigão, ERICA), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (small-flowered morning glory, IAQTA), Ipomoea hederacea (L.) Jacq. (jeticuçu, IPOHE), Ipomoea lacunosa L. (morning glory, IPOLA), Lactuca serriola L./Torn. (wild lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Sida spinosa L. (black broom, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptycanthum Dunal (nightshade, SOLPT) or Xanthium strumarium L. (common burr, XANST).

[0071] In some embodiments, application rates of about 1 to about 4,000 grams/hectare (g/ha) are employed in post-emergency operations. In some embodiments, rates of about 1 to about 4,000 g/ha are employed in pre-emergency operations.

[0072] The compounds, compositions and methods described herein are used to control undesirable vegetation in crops tolerant to 5-enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitors (e.g., glyphosate tolerant), tolerant to glutamine synthetase inhibitors (e.g. glufosinate tolerant), synthetic auxin tolerant (e.g. dicamba tolerant, phenoxy auxin tolerant, pyridyloxy auxin tolerant), auxin transporter inhibitor tolerant, acetyl CoA carboxylase (ACCase) inhibitor tolerant (e.g., aryloxyphenoxy propionate tolerant), acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor tolerant (e.g., imidazolinone tolerant, sulfonylurea tolerant, pyrimidinylthiobenzoate tolerant, triazolopyrimidine tolerant, sulfonylamino carbonyl tolerant triazolinone), tolerant to 4-hydroxyphenyl pyruvate dioxygenase (HPPD) inhibitors, tolerant to protoporphyrinogen oxidase (PPO) inhibitors, tolerant to photosystem (PS) II inhibitors (e.g., triazine tolerant and bromoxynil tolerant) (such as , but not limited to, soybeans, cotton, canola/oilseed rape, rice, cereals, corn, peat, etc.), for example, in conjunction with EPSP synthase inhibitors (e.g. glyphosate), glutamine synthase inhibitors (e.g. glufosinate), synthetic auxins (e.g., dicamba, phenoxy auxins, pyridyloxy auxins), ACCase inhibitors (e.g., aryloxyphenoxypropionates), ALS inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinyl thiobenzoates, triazolopyrimidines, and sulfonylamino carbonyltriazolinones), HPPD, PPO inhibitors and PS II inhibitors (e.g. triazines and bromoxynil). The compositions and methods can be used to control undesirable vegetation in crops that have multiple or accumulated aspects that confer tolerance to multiple chemicals and/or inhibitors of multiple modes of action.

[0073] The compounds and compositions provided herein can also be used to control herbicide-resistant or tolerant weeds. Examples of resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to ALS (or AHAS) inhibitors, PS II inhibitors, ACCase inhibitors, synthetic auxins, PS I inhibitors, EPSP synthase inhibitors, microtubule assembly inhibitors, lipid synthesis inhibitors, PPO inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, HPPD inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes of action such as quinclorac and unclassified herbicides such as arylamino propionic acids, diphenzoquat, endothal and organo arsenic acids. Examples of resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, multiple chemical classes, and multiple herbicide modes of action.

[0074] The embodiments described and examples below are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses or combinations with respect to the compositions described herein will be apparent to a person of ordinary skill in the art without departing from the scope of the claimed subject matter.

Examples Example 1: Preparation of 7-fluoro-1-(triisopropylsilyl)-1H-indole (1)

[0075] The title compound was prepared according to the literature procedure Das, A., et al. Org. Lett. 2017, 19, 5794 - 5797, which is incorporated herein by reference in its entirety. Example 2: Preparation of 7-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole (2)

[0076] The title compound was prepared as in Preparation 50, Precursor Example 3 in US patent application publication no. 2014/0274695. Example 3: Preparation of methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinate (3)

[0077] The title compound can be prepared as described in Example 1 in US patent application publication no. 2014/0274695. Alternatively, it can be prepared as follows.

[0078] To a 3 liter (L) three-necked flask, equipped with magnetic stirring, condenser, internal temperature sensor and nitrogen atmosphere, methyl 4-amino-3,6-dichloro-5-fluoropicolinate ( prepared as in Fields et al., Tetrahedron Letters 2010, 51, 79 - 81; 75 grams (g), 314 millimoles (mmol)) and 7-fluoro-6-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole (175 g, 377 mmol). Acetonitrile (CH3CN; 1255 milliliters (mL)) and a 2 molar (M) potassium phosphate solution (314 mL, 628 mmol) were added sequentially. The mixture was then evacuated and filled with nitrogen (3x) before adding palladium bis-(triphenylphosphine) dichloride (11.12 g, 15.69 mmol). The flask was evacuated and filled (3x), and the mixture was heated to 65°C. After 3 hours (h), potassium fluoride (74.4 g, 1255 mmol) was added and heating was continued for another 16 h. The reaction mixture was allowed to cool and was filtered through Celite. The phases were separated and the solvent was removed under reduced pressure. The residue was triturated with hexane and the solid was collected by filtration and washed with hexane. The resulting solid was treated with dichloromethane (CH2Cl2), filtered, rinsed with a small amount of CH2Cl2 and dried in vacuum at 50°C. The title compound was isolated as a beige solid (73.5 g, 69%). Example 4: Preparation of 4-amino-3-chloro-5-fluoro-6- (7-fluoro-1H-indol-6-yl) picolinic acid (4)

[0079] The title compound can be prepared as in Example 12 in US patent application publication no. 2014/0274695 or as follows.

[0080] Methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinate (288 milligrams (mg), 0.853 mmol) was dissolved in tetrahydrofuran (THF ; 2.0 mL), methanol (CH3OH; 2.0 mL) and water (1.0 mL). Lithium hydroxide hydrate (100 mg, 2.383 mmol) was added. The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was concentrated until dry. The resulting solid was diluted with water and the suspension was acidified (pH ~ 3). The suspension was extracted with ethyl acetate (EtOAc; 3x). The combined organic extracts were washed with saturated aqueous sodium chloride (NaCl), dried over magnesium sulfate (MgSO4), filtered and concentrated. The title compound was isolated as a beige solid (256 mg, 93%). Example 5: Preparation of prop-2-yn-1-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinate (5)

[0081] A mixture of 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid (1.5 g, 4.63 mmol), potassium carbonate (0.833 g, 6.02 mmol) and 3-bromopropine (0.549 mL, 5.10 mmol) in N,N-dimethylformamide (DMF; 18.5 mL) was stirred at room temperature for 4 h. The reaction mixture was poured into a half-saturated aqueous solution of sodium bicarbonate (NaHCO3) and extracted with EtOAc (2x). The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by automated flash chromatographic column (silica gel, hexane/EtOAc gradient). To the resulting oil, a minimum of CH2Cl2 was added to initiate crystallization. Sonication was further used to facilitate crystallization. Hexane was then added to further precipitate the product. The solid was filtered, washed with hexane (2x) and dried in vacuo. The title compound was isolated as a white solid (1.33 g, 79%): melting point 140 - 142°C; 1H NMR (400 MHz, CDC13) δ 8.49 (s, 1H), 7.49 (dd, J = 8.3, 0.7 Hz, 1H), 7.32 - 7.27 (m, 2H) , 6.61 (td, J = 3.3, 2.1 Hz, 1H), 4.97 (d, J = 2.5 Hz, 2H), 4.91 (s, 2H), 2.53 ( t, J = 2.5 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ -135.47, -135.55, -137.23, -137.32; ESIMS m/z 362 ([M+H]+).

[0082] The following compound was synthesized as in Example 5. Cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinate (6)

[0083] The title compound was isolated as a white solid (730 mg, 65%): melting point 139 - 140°C; 1H NMR (300 MHz, DMSO-d6) 11.83 (s, 1H), 7.52 (d, J = 3.1 Hz, 1H), 7.47 (d, J = 8.2 Hz, 1H) , 7.13 - 7.03 (m, 3H), 6.59 (t, J = 3.2 Hz, 1H), 5.29 (s, 2H); ESIMS m/z 363 ([M+H]+). Example 6: Assessment of post-emergence herbicide activity in greenhouses

[0084] Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mix, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30%, in plastic pots with a surface area of 103.2 square centimeters (cm2). When necessary to ensure good germination and healthy plants, a fungicidal treatment and/or other chemical or physical treatment was applied. Plants were grown for 7 to 36 days (d) in a greenhouse with a light period of approximately 14 hours (h), which was maintained at approximately 18°C during the day and 17°C at night. Nutrients and water were added regularly and supplemental lighting was provided with 1000-watt metal halide lamps as needed. Plants were used for testing when they reached the second or third true leaf stage.

[0085] An aliquot of the formulated Compound 5 (100 grams of acid equivalent per liter (g ae/L); emulsifiable concentrate (EC)), Compound 6 (100 g ae/L; EC) or Compound 7 (100 g ae /L; EC) was placed in a 25 mL glass vial and diluted in a volume of 1.25% (volume by volume (v/v)) aqueous esterified rapeseed oil Actirob B to obtain a stock solution. The concentrated stock solutions were diluted with an aqueous mixture of 1.25% v/v Actirob B aqueous esterified rapeseed oil to provide adequate application rates. Compost requirements are based on an application volume of 12 mL at a rate of 187 liters per hectare (L/ha). The formulated compounds were applied to plant material with an overhead Mandel tray sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m2) at a spray height of 18 inches (43 centimeters). cm)) above the average plant canopy. Control plants were sprayed in the same way with the white solvent.

[0086] The treated plants and control plants were positioned in a greenhouse as described above and watered by sub-irrigation to avoid washing out the test compounds. After 20 - 22 d, the condition of the test plants, compared to the control plants, was determined visually and scored on a scale of 0 to 100%, where 0 corresponds to no injury and 100 corresponds to complete death. The condition of the test plants was compared to that of the control plants, as determined visually and scored on a scale of 0 to 100%, where 0 corresponds to no injury and 100 corresponds to complete death.

[0087] Weed control was assessed visually (as percentage (%) of visual control) at intervals indicated in the tables. The values reported are averages. Means followed by the same letter in the tables do not differ significantly (P = 0.5, Duncan's new multiple range test). Data are summarized in Table 1. Example 7: Assessment of post-emergence herbicide activity in field trials in Canada

[0088] Field trials were established in Canada (in Ellerslie, Alberta; Nisku, Alberta and Hanley, Saskatchewan) to evaluate the efficacy of Compound 5, Compound 6 and Compound 7. The trials were designed as randomized complete blocks with three to four replicates. Trials were established on spring wheat with a natural weed population with plot sizes of 2 - 3 meters (m) by 8 - 10 m (width x length). The crops were grown using normal cropping practices for fertilization, sowing and maintenance to ensure good crop growth.

[0089] All herbicide treatments were applied in post-emergence applications made to crops at the BBCH growth stage (Stages of Phenological Development of a Plant) 14 and 22. The herbicides were applied with backpack or bicycle sprayers using carbon dioxide. carbon (CO2) as propellant. The sprayers utilized calibrated flat fan air induction spray nozzles to provide a uniform spray pattern that provided complete foliage coverage using a spray volume of 100 L/ha. All treatments were applied with methylated seed oil (MSO) at 1.25% v/v. Phytotoxicity to weeds was assessed visually at various intervals after application as an overall percentage of control compared to an untreated control batch. In general, three to four replicates were evaluated for each treatment. All treatment results are an average of three or four replicates. Herbicide treatments

[0090] Compound 5, compound 6 and compound 7 were applied as emulsifiable concentrate (EC) formulations at 100 g ae/L EC, respectively.

[0091] The results are provided in Table 2 through Table 4. Example 8: Assessment of post-emergence herbicidal activity in field trials in Spain and Germany

[0092] Field trials were established in Spain (Banares and Granon) and Germany (Bielefeld) to evaluate the effectiveness of Compound 5, Compound 6 and Compound 7. The trials were designed as randomized complete blocks with three to four replicates. Trials were established on winter wheat with a natural weed population with plot sizes of 2 - 2.5 meters (m) by 6 - 8 m (width x length). The crops were grown using normal cropping practices for fertilization, sowing and maintenance to ensure good crop growth.

[0093] All herbicide treatments were applied in post-emergency applications made to crops at the BBCH 21 to 23 growth stage. Herbicides were applied with backpack or bicycle sprayers using air as a propellant. The sprayers utilized calibrated flat fan air induction spray nozzles to provide a uniform spray pattern that provided complete foliage coverage using a spray volume of 200 L/ha. All treatments were applied with methylated seed oil (MSO) at 1.25% v/v. Phytotoxicity to weeds was assessed visually at various intervals after application as an overall percentage of control compared to an untreated control batch. In general, three to four replicates were evaluated for each treatment. All treatment results are an average of three or four replicates. Herbicide treatments

[0094] Compound 5, compound 6 and compound 7 were applied as emulsifiable concentrate (EC) formulations at 100 g ae/L of EC, respectively.

[0095] The results are provided in Table 5 through Table 8.

[0096] The following abbreviations are used in Tables 1 to 8:

[0097] Compound 5 = 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) prop-2-yn-1-yl picolinate

[0098] Compound 6 = 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)cyanomethyl picolinate

[0099] Compound 7 = benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinate CENCY = Centaurea cyanus (corn flower) CHEAL = Chenopodium album L. (common terns) CIRAR = Cirsium arvense (L.) Scop. (vine thistle) FUMOF = Fumaria officinalis (common smoker) KCHSC = Kochia scoparia (L.) Schrad. (kochia) MATCH = Matricaria recutita L. (wild chamomile) MATIN = Matricaria odorless (scentless weed) PAPRH = Papaver rhoeas L. (common poppy) Res-PAPRH = Papaver rhoeas L. (common poppy) which is resistant to tribenuron and thifensulfuron (ALS - mode of action of acetolactate synthase) and 2,4-D POLCO = Polygonum convolvulus L. (wild buckwheat) SINAR = Sinapis arvensis L. (wild mustard) STEME = Stellaria media (L.) Vill. (common chickweed) VERHE = Veronica hederifolia (ivy-leaved veronica) VERSS = Veronica spp (veronica) g ae/ha = grams of acid equivalent per hectare LSD = least significant difference DAAA = days after application Table 1 : Percentage (%) of visual control of key weeds by herbicide compounds under greenhouse conditions Table 2: Percentage (%) of visual control of key weeds by herbicidal compounds under field conditions in Hanley, Saskatchewan, Canada (66 days after application A (66 DAAA)) Percentage (%) of visual control 66 DAAA Table 3: Percentage (%) of visual control of key weeds by herbicidal compounds under field conditions in Nisku, Alberta, Canada (28 - 51 days after application A (28 - 51 DAAA)) Table 4: Percentage (%) visual control of key weeds by herbicide compounds under field conditions in Ellerslie, Alberta, Canada (51 days after application A (51 DAAA)) Table 5: Percentage (%) of visual control of key weeds by herbicidal compounds under field conditions in Granon, Spain (34 - 84 days after application A (34 - 84 DAAA)) Table 6: Percentage (%) of visual control of key weeds by herbicidal compounds under field conditions in Banares, Spain (66 - 83 days after application A (66 - 83 DAAA)) Table 7: Percentage (%) of visual control of key weeds by herbicidal compounds under field conditions in Granon, Spain (48 - 68 days after application A (48-68 DAAA)) Table 8: Percentage (%) of visual control of key weeds by herbicidal compounds under field conditions in Bielefed, Germany (85 days after application A (85 DAAA))

[0100] As can be seen from the above-mentioned results, the present compounds of Formula (I) exhibit herbicidal activity. As can also be seen from the above-mentioned results, Compound 5 and Compound 6 demonstrated superior herbicidal activity over Compound 7. These new chemical herbicides offer a broader spectrum of weed control, greater activity against weeds and provide a way to approach the management of weeds that have developed resistance to the herbicides traditionally used to control them.

[0101] Although this disclosure has been described as presenting examples of aspects or embodiments, the present disclosure may be further modified within the scope of this disclosure. Accordingly, this application is intended to cover any variations, uses or adaptations of the disclosure using its general principles. Furthermore, this application is intended to cover deviations from the present disclosure that fall within known or customary practice in the art to which this disclosure relates.

[0102] The benefits, advantages, solutions to problems and any elements that may cause or make any benefit, advantage or solution more pronounced should not be interpreted as critical, required or essential characteristics or elements. The scope must therefore be limited by nothing other than the appended claims, in which reference to an element in the singular is not intended to mean “one and only one” unless explicitly stated, but rather “one or more”. Furthermore, when a phrase similar to “at least one of A, B, or C” is used in the claims, the phrase is intended to be interpreted as meaning that A alone may be present in an embodiment, B alone may be present in one embodiment, C alone may be present in one embodiment, or any combination of the elements A, B or C may be present in a single embodiment; for example, A and B, A and C, B and C, or A and B and C.

[0103] Here, in the detailed description, references to “the embodiment”, “an embodiment”, “an exemplary embodiment”, etc., indicate that the described embodiment may include a particular feature, structure or characteristic, however, each embodiment may does not necessarily include the particular feature, structure or characteristic. Furthermore, such phrases do not necessarily refer to the same embodiment. Furthermore, when a particular feature, structure or characteristic is described in connection with an embodiment, it is alleged to be within the knowledge of one skilled in the art, with the benefit of the present disclosure, to affect such feature, structure or characteristic in connection with other embodiments, whether explicitly described or not.

Claims (13)

1. Compound of Formula (I): characterized by the fact that: X is CY, where Y is halogen; R1 is C3-C12 alkynyl or C1-C3 alkyl substituted with CN; R2 is halogen; R3 and R4 are independently hydrogen; R be halogen; R6 and R6' are independently hydrogen; R7 and R7' are independently hydrogen; R8 is hydrogen; or an agriculturally acceptable salt thereof. 2. Compound, according to claim 1, characterized by the fact that: X is CF, CCl or CBr; R2 will be chlorine. 3. Compound, according to claim 1, characterized by the fact that: X is CF; 4. Compound according to claim 3, characterized in that R2 is Cl. 5. Compound according to claim 3, characterized in that R2 is Cl. characterized by the fact that R5 is F. 6. Compound according to claim 4, characterized in that R5 is F. 7. Compound according to claim 5, characterized in that the compound is prop-2-yn-1-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole- 6-yl) picolinate. 8. Compound according to claim 5, characterized in that the compound is cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinate. 9. Herbicidal composition characterized by the fact that it comprises the compound as defined in claim 1 and an agriculturally acceptable adjuvant or carrier. 10. Composition, according to claim 9, characterized by the fact that it further comprises at least one additional herbicidal compound. 11. Composition, according to claim 9, characterized by the fact that it further comprises a protector. 12. Method for controlling undesirable vegetation characterized by the fact that it comprises: providing the compound as defined in claim 1; and apply the compound to undesirable vegetation or the location thereof. 13. Method for controlling undesirable vegetation characterized by the fact that it comprises: providing the composition as defined in claim 9; and applying the composition to undesirable vegetation or the location thereof.