Pyridazinone herbicides and pyridazine intermediates used to prepare a herbicide.
Patent Information
- Application Number
- MX2021003530
- Authority / Receiving Office
- MX · MX
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2018-09-27
- Filing Date
- 2021-03-25
- Publication Date
- 2026-02-25
- Estimated Expiration
- 2039-09-26
AI Technical Summary
There is a need for improved herbicidal pyridazinones and methods for preparing them, as existing pyridazinones and their synthetic intermediates do not effectively address the challenges of selective weed control in various crops.
The development of pyridazinones and processes for preparing pyridazinone-based herbicides, including specific compounds of Formula I and their derivatives, through reactions with magnesium, methoxylating agents, tmp-zinc bases, halogenating agents, and demethylating agents, to enhance herbicidal efficacy.
The described processes yield compounds with improved herbicidal properties, allowing for selective control of weeds in crops such as wheat, barley, corn, soybeans, sunflower, cotton, rapeseed, rice, sugarcane, citrus, and nut crops, with enhanced efficacy and broader spectrum of weed control.
Abstract
Description
PYRIDAZINONE HERBICIDES AND PYRIDAZINONE INTERMEDIATES USED TO PREPARE A HERBICIDE Field of Invention The present disclosure provides pyridazinones and processes for preparing pyridazinones. The pyridazinones described herein can be used as synthetic intermediates for preparing pyridazinone-based herbicides or used as pyridazinone herbicides. WO 2015 / 168010 and WO 2017 / 074988 describe pyridazinones herbicides and synthetic intermediates used to prepare pyridazinones herbicides. There is a need for improved herbicidal pyridazinones and improved methods for preparing herbicidal pyridazinones. Brief Description of the Invention In one aspect, the present disclosure provides a compound of Formula I and / V-oxides or salts thereof, ncccnn / i 7Π7 / Β / Υ wherein R1 is C1-C4 alkyl or Cs-Ce cycloalkyl; R2 is H, Cl, Bro I; R3 is Cl or OR4; R4 is H or C1-C4 alkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl. In another aspect, the present disclosure provides a process for preparing a compound of Formula I-A ncccnn / i ζηζ / Β / γ where R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R2 is H or Cl; R5 is H, F, Cl or CH3; and RBes H or Cl the process comprises: (1) reacting a compound of Formula II br II R5 where R5 is H, F, Cl or CH3; and RBes H or Cl with magnesium to form an intermediate of Formula III Br^Mg II R5; and (2) reacting the intermediate compound or Formula III formed in (1) with a compound of Formula IV-A or IV-B or ncccnn / i ζπζ / β / υιλι where R1 is C1-C4 alkyl or Cs-Ce cycloalkyl; G is C1-C4 alkyl, SO2CF3 or SO2(4-Me-Ph). In another aspect, the present disclosure provides a process for preparing a compound of Formula 1-B where R1 is C1-C4 alkyl or Cs-Ce cycloalkyl; R5 is H, F, OI or CH3; and R6 is H or Cl The process comprises reacting a compound of Formula 1-A, as set forth above where R2 is H, with a methoxylating agent. In another aspect, the present disclosure provides a process for preparing a compound of Formula 1-C where R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R2 is Cl, Br or I; R5 is H, F, Cl or CH3; and R6 is H or Cl the process comprises: (1) reacting a compound of Formula 1-B, as set forth above, with a tmp-zinc base, to form a zinc-plated intermediate of Formula V ncccnn / i 7Π7 / Β / Υ (2) reacting the compound zinc intermediate of Formula V formed in (1) with a halogenating agent. In another aspect, the present disclosure provides a process for preparing a compound of Formula 1-D wherein R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R2 is Cl, Bro I; R5 is H, F, Cl or CH3; and R6 is H or Cl The process comprises reacting a compound of Formula 1-C, as set forth above, with a demethylating agent. In another aspect, the present disclosure provides a further process for preparing a compound of Formula 1-E ncccnn / i 7Π7 / Β / Υ where R1 is C1-C4 alkyl or Cj-Ce cycloalkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process comprises reacting a compound of Formula VI saw where R1 is C1-C4 alkyl or Cs-Ce cycloalkyl R5 is H, F, Cl or CH3; and R6 is H or Cl with phosphorous oxychloride. In another aspect, the present disclosure provides a further process for preparing a compound of Formula 1-E ncccnn / i ζπζ / β / υ where R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process includes: (1) reacting a compound of Formula II br TT R5 where R5 is H, F, Cl or CH3; and R6 is H or Cl; with magnesium to form an intermediate compound of Formula III Br^Mg II R5; and (2) reacting the intermediate compound or Formula III formed in (1) with a compound of Formula 7 ncccnn / i ζηζ / Β / γ where R1 is C1-C4 alkyl or Cs-Ce cycloalkyl. Detailed description of the invention As used herein, the terms "comprising", "comprising", "includes", "including", "has", "having", "contains", "containing", "characterized by" or any other variations hereof are intended to cover non-exclusive inclusion, subject to any explicitly stated limitations. For example, a process or method comprising a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition process or method. The transition phrase "consisting of" excludes any unspecified element, stage, or ingredient. If in the claim, this would close the claim to the inclusion of materials other than those listed except for impurities normally associated with them. When the phrase "consisting of" appears in a clause of the body of a claim, instead of immediately following the preamble, it limits only the element stated in that clause; other elements are not excluded from the claim as a whole. The transition phrase "consisting essentially of" is used to define a process or method that includes materials, steps, features, components, or items, in addition to those described literally, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel features of the description. The term "consisting essentially of" occupies a foreground between "comprising" and "consisting of". Where applicants have defined the description or a part thereof with an indefinite term such as "comprising", it should be readily understood that (unless otherwise stated) the description should also be construed to describe such description using the terms " consisting essentially of” or “consisting of”. In addition, unless expressly stated otherwise, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by either of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). Also, the indefinite articles “a” and “uno / una” that precede an element or component of the description are intended not to be restrictive with respect to the number of instances (ie occurrences) of the element or component. Thus "a" or "a / an" should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously intended to be singular. As used herein, the term "Ci-Ce alkyl" includes straight-chain or branched alkyl groups having one to six carbon atoms, for example, methyl, ethyl, n-propyl, / -propyl, or the various isomers. butyl, pentyl, or hexyl. Likewise, the term "C1-C4 alkyl" includes branched or straight chain alkyl having one to four carbon atoms, for example, methyl, ethyl, n-propyl, / -propyl, or the different butyl isomers, and the The term "C1-C3 alkyl" includes methyl, ethyl, n-propyl, and / -propyl. As used herein, the term "halogen" includes fluoro, chloro, bromo or iodo. When G is "SO2(4-Me-Ph)" this is alternatively defined as "S02(p-tolyl)". The term "reacting" and the like refer to adding, contacting, or mixing two or more reactants under appropriate conditions to produce the indicated and / or desired product. It should be appreciated that the reaction that produces the indicated and / or the desired product may not necessarily result directly from the combination of two reactants that were initially added, that is, there may be one or more intermediates that occur in the mixture that ultimately leads to to the formation of the indicated and / or the desired product. Reacting can take place in the presence or absence of solvent, at a temperature above or below room temperature, under an inert atmosphere, etc. The term "methoxylating agent" as used herein refers to a chemical reagent used to add a methoxy group, that is, OCH3, to a compound. Exemplary non-limiting methoxylating agents include sodium methoxide or potassium methoxide. The term "tmp-zinc base" as used herein refers to a chemical complex comprising zinc and 2,2,6,6-tetramethylpiperidine. Exemplary non-limiting zinc bases include (tmp)2Zn-2 MgCb-2 LiCI. (tmp)2Zn-2 LiCI and (tmpjzZn. The term "halogenating agent" as used herein refers to a chemical reagent used to add a halogen atom, eg, Cl, Br, or I, to a compound. Exemplary non-limiting halogenating agents include iodine, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin , trichloroisocyanuric acid, sulfuryl chloride, N-bromosuccinimide and / V-chlorosuccinimide. compounds of Formula I typically exist in more than one solid form. Thus, the compounds of Formula I include all crystalline and non-crystalline forms of the compounds they represent. Non-crystalline forms include modalities that are solid such as waxes and gums as well as modalities that are liquid such as orodispersible tablets and solutions. Crystal forms include modalities that essentially represent a single crystal type and modalities that represent a mixture of polymorphs (ie different crystal types). The term "polymorph" refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different configurations and / or conformations of the molecules in the crystal lattice. Although polymorphs may have the same chemical composition, also ncccnn / i 7Π7 / Β / Υ may differ in composition due to the presence or absence of co-crystallized water or other molecules, which may be loosely or strongly linked in the lattice. Polymorphs may differ in such chemical, physical, and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate, and biological availability. One skilled in the art will appreciate that one polymorph of a compound of Formula I may exhibit beneficial effects (eg, convenience for the preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound of Formula I. Formula I. The preparation and isolation of a particular polymorph of a compound of Formula I can be accomplished by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures. For a comprehensive discussion of polymorphism see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, WileyVCH, Weinheim, 2006. Synthetic methods for the preparation of / V-oxides of heterocycles and tertiary amines are well known to one skilled in the art. Exemplary procedures for preparing / V-oxides include the oxidation of heterocycles and tertiary amines with peroxyacids such as peracetic and m-chloroperbenzoic acid (MCPBA), acid peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as as dimethyldioxirane. These methods for the preparation of / V-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S.V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M.R. Grimmett and B.R.T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A.R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A.R. Katritzky and A.J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A.J. Boulton, Eds., Academic Press. That said, one skilled in the art will appreciate that not all nitrogen-containing heterocycles can form / V-oxides since nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles that can form / V-oxides. One skilled in the art recognizes that because in the environment and under physiological conditions the salts of chemical compounds are in equilibrium with their corresponding non-salt forms, the salts share the biological utility of the non-salt forms. Thus, a wide variety of salts of a compound of Formula I are useful for the control of unwanted vegetation (ie they are agriculturally suitable). Salts of a compound of Formula I include acid addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric. Accordingly, the present disclosure comprises compounds selected from Formula I, / V-oxides and suitable agricultural salts thereof. ncccnn / i 7Π7 / Β / Υ The embodiments of the present disclosure (where a compound of Formula I includes a compound of Formula I-A, I-B, I-C, I-D and I-E) also include / V-oxides and / or salts thereof): A. A compound of formula i Modality A1. A compound of Formula I and / V-oxides or salts thereof as described in the Brief Description of the Invention. A2 modality. The compound of Mode A1 wherein R1 is C1-C4 alkyl. A3 modality. The compound of any one of Modalities Α1 or A2 where R1 is CH3. A3A modality. The compound of any one of Modalities A1 through A3 where R2 is Cl. A4 mode. The compound of any one of Modalities A1 through A3 where R2 is Br. A5 mode. The compound of any one of Modalities A1 through A4 where R3 is Cl. Modality A6. The compound of any one of Modalities A1 through A4 wherein R3 is OR4; and R4 is H. Modality A7. The compound of any one of Modalities A1 through A4 wherein R3 is OR4; and R4 is C1-C4 alkyl. Modality A8. The compound of any one of Modalities A1 through A4 wherein R3 is OR4; and R4 is CH3. Modality A9. The compound of any of the Modalities A1 to A8 where R5 is F. Modality A10. The compound of any one of Modalities A1 through A8 where R5 is Cl. Modality A11. The compound of any one of Modalities A1 through A8 wherein R5 is CH3. Modality A12. The compound of any one of Modalities A1 through A8 where R5 is H. Modality A13. The compound of any one of Modalities A1 through A12 where R6 is H. Modality A14. The compound of any one of Modalities A1 through A12 where R6 is Cl. Modality A15. The compound of Embodiment A1 wherein R1 is CH3 and R2, R3, R4, R5 and R6 of Formula I are as defined in Table AA. ncccnn / i 7Π7 / Β / Υ TABLE AA Com. No. R2 R3 R4 R5 Rs 1 H Cl — H H 2 H Cl __ F H Com. No. R2 R3 R4 R5 R6 3 H Cl — Cl H 4 H Cl — ch3 H 5 Cl Cl — H H 6 Cl Cl — F H 7 Cl Cl — Cl H 8 Cl Cl — ch3 H 9 Br Cl — H H 10 Br Cl — F H 11 Br Cl — Cl H 12 Br Cl — ch3 H 13 I Cl — H H 14 I Cl — F H 15 I Cl — Cl H 16 I Cl — ch3 H 17 H OR4 H Cl H 18 H OR4 H ch3 H 19 H OR4 H F H 20 Cl OR4 H ch3 H 21 Cl OR4 H F H 22 Cl OR4 H Cl H 23 Br OR4 H F H 24 Br OR4 H Cl H 25 Br OR4 H ch3 H 26 I OR4 H F H 27 I OR4 H Cl H 28 I OR4 H CH3 H 29 H OR4 CH3 H H 30 H OR4 ch3 F H 31 H OR4 ch3 Cl H 32 H OR4 ch3 CH3 H 33 Cl OR4 ch3 H H 34 Cl OR4 ch3 F H 35 Cl OR4 ch3 Cl H 36 Cl OR4 ch3 CH3 H 37 Br OR4 ch3 H H 38 Br OR4 ch3 F H 39 Br OR4 ch3 Cl H ncccnn / i ζηζ / Ε / γ Com. No. R2 R3 R4 R5 R6 40 Br OR4 CH3 ch3 H 41 I OR4 ch3 H H 42 I OR4 ch3 F H 43 I OR4 ch3 Cl H 44 I OR4 ch3 ch3 H 45 H Cl — H Cl 46 H Cl — F Cl 47 H Cl — Cl Cl 48 H Cl — ch3 Cl 49 Cl Cl — H Cl 50 Cl Cl — F Cl 51 Cl Cl — Cl Cl 52 Cl Cl — CH3 Cl 53 Br Cl — H Cl 54 Br Cl — F Cl 55 Br Cl — Cl Cl 56 Br Cl — CH3 Cl 57 I Cl — H Cl 58 I Cl — F Cl 59 I Cl — Cl Cl 60 I Cl — ch3 Cl 61 H OR4 H H Cl 62 H OR4 H F Cl 63 H OR4 H Cl Cl 64 H OR4 H ch3 Cl 65 Cl OR4 H H Cl 66 Cl OR4 H F Cl 67 Cl OR4 H Cl Cl 68 Cl OR4 H ch3 Cl 69 I OR4 H H Cl 70 I OR4 H F Cl 71 I OR4 H Cl Cl 72 I OR4 H CH3 Cl 73 H OR4 ch3 H Cl 74 H OR4 ch3 F Cl 75 H OR4 ch3 Cl Cl 76 H OR4 ch3 ch3 Cl ncccnn / i 7Π7 / β / υ Com. No. R2 R3 R4 R5 R6 77 Cl OR4 CH3 H Cl 78 Cl OR4 CH3 F Cl 79 Cl OR4 ch3 Cl Cl 80 Cl OR4 ch3 CHs Cl 81 Br OR4 ch3 H Cl 82 Br OR4 ch3 F Cl 83 Br OR4 ch3 Cl 84 Br OR4 CH3 CH3 Cl 85 I OR4 CH3 H Cl 86 I OR4 CH3 F Cl 87 I OR4 CH3 Cl 88 I OR4 ch3 ch3 Cl ncccnn / i ζηζ / Β / γ Modality A16. A compound of Mode A1 (this is a compound of Formula I selected from 5-chloro-2-methyl-4-(2-methyl-1-naphtha-lenyl)-3(2 / - / )-pyridazinone; 5-chloro-4-(2,7-dimethyl-1-naphthalenyl)-2-methyl-3(2 / - / )-pyridazinone; 5-methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone; 4-(2,7-dimethyl-1-naphthalene)-5-methoxy-2-methyl-3(2 / - / )-pyridazinone; 6-chloro-5-methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone; and 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-methoxy-2-methyl-3(2 / - / )-pyridazinone. Modality A17. The composite of Mode A1 provided that (a) when R3 is OR4; R4 is H; and R5 is H, so Re is Cl; and (b) when R2 is Br: R3 is OR4; and R4 is H, so R6 is H. B. A process for preparing a compound of Formula 1-A Modality B1. A process as described in the Brief Description of the Invention for preparing a compound of Formula 1-A. B2 mode. The process of Mode B1 where R1 is C1-C4 alkyl. Modality B3. The process of one of either Modes Β1 or B2 where R1 is CH3. Modality B4. The process of one of any of the Modalities B1 to B3 where R2 is Cl. Modality B5. The process of any one of the Modalities B1 to B3 where R2 is Br. Modality B6. The process of one of any of the Modalities B1 to B5 where R5 is F. Modality B7. The process of any one of Modality B1 to B5 where R5 is Cl. Modality B8. The process of any one of Modes B1 through B5 where R5 is CH3. Modality B9. The process of one of any of the Modalities B1 to B5 where R5 is H. Modality B10. The process of one of any of the Modalities B1 to B9 where R6 is H. Modality B11. The process of one of any of the Modalities B1 to B9 where R6 is Cl. Modality B12. The process of Embodiment B1 wherein the compound of Formula 1-A is selected from the group consisting of Com. No. 1, 2, 3, 4, 5, 6, 7, 8, 45, 46, 47, 48, 49, 50, 51 and 52 (this is a compound of Formula I where R1 is CH3; R5 is H, F, Cl, or CH3; R2 is H; R3 is Cl; and R6 is H or Cl, as listed in TABLE BB). TABLE BB ncccnn / i 7Π7 / Β / Υ Com. No. R2 R3 R5 R6 1 H Cl H H 2 H Cl F H 3 H Cl Cl H 4 H Cl ch3 H 5 Cl Cl H H 6 Cl Cl F H 7 Cl Cl Cl H 8 Cl Cl ch3 H 45 H Cl H Cl 46 H Cl F Cl 47 H Cl Cl Cl 48 H Cl ch3 Cl 49 Cl Cl H Cl 50 Cl Cl F Cl 51 Cl Cl Cl Cl 52 Cl Cl ch3 Cl Modality B13. The process of any one of Modes B1 through B12 wherein a compound of Formulas II or III is as described in the Brief Description of the Invention. Modality B14. The process of Modality B13 where R5 is F. Modality B15. The process of Modality B13 where R5 is Cl. Modality B16. The process of Mode B13 where R5 is CH3. Modality B17. The process of Mode B13 where R5 is H. Modality B18. The process of one of any of the Modalities Β1 or B13 up to B17 where R6 is H. Modality B19. The process of any of the Modalities B13 to B17 where RB is Cl. Modality B20. The process of any one of Modalities B13 through B17 wherein a compound of Formulas IV-A or IV-B is as defined in the Brief Description of the Invention. Modality B21. The process of Mode B20 where R1 is C1-C4 alkyl. Modality B22. The process of Embodiment B20 where R1 is Cs-Ce cycloalkyl. Modality B23. The process of Mode B20 where R1 is CH3. Modality B24. The process of any one of Modes B20 through B23 where G is Ci-Ce alkyl. Modality B25. The process of Mode B24 where G is CH3. Modality B26. The process of any one of Embodiments B1 through B25 further comprises isolating the compound of Formula 1-A. Modality B27. The process of any one of Modalities B1 to B26 wherein the reacting of a compound of Formula II with magnesium is carried out in a suitable solvent. Modality B28. The process of Embodiment B27 wherein reacting a compound of Formula II with magnesium is carried out in tetrahydrofuran. Modality B29. The process of any of the Modalities B1 to B28 wherein the reaction of a compound of Formula II with magnesium is carried out at a temperature above 80°C. Modality B30. The process of any of Modes B1 through B28 wherein the reacting is carried out at a temperature at or below 0°C. Modality B31. The process of any of Modes B1 to B30 wherein the reacting is carried out at a temperature of from about 0°C to about 80°C. C. A process for preparing a compound of Formula 1-B C1 mode. A process as described in the Brief Description of the Invention for preparing a compound of Formula 1-B. Mode 02. A process of Mode 01 where R1 is C1-C4 alkyl. Mode 03. The process of Mode 02 where R1 is CH3. Modality 04. The process of one of any of the Modalities C1 to 03 where R5 is F. Modality 05. The process of any of the Modalities C1 to 03 where R5 is Cl. Modality 06. The process of any one of Modality C1 to 03 where R5 is CH3. Modality 07. The process of any of Modality C1 to 03 where R5 is H. Modality 08. The process of any of the Modalities C1 to 07 where R6 is H. Modality 09. The process of any of the Modalities C1 to 07 where R6 is Cl. ncccnn / i 7Α7 / β / υιλι Modality C10. The process of any one of Modalities C1 through C9 wherein the compound of Formula 1-B is selected from the group consisting of Com. Nos. 29, 30, 31, 32, 73, 74, 75 and 76 (i.e. Compounds of Formula I wherein R1 is CH3; R2 is H; R3 is OR4; R4 is CH3; R5ncccnn / i 7Π7 / Β / Υ is H, F, Cl 0 CH3; and R6 is H 0 Cl; as listed in TABLE CC). Com. No. CC TABLE R6 R2 R3 -R4 R5 29 H OR4 CH3 H H 30 H OR4 ch3 F H 31 H OR4 ch3 Cl H 32 H OR4 ch3 ch3 H 73 H OR4 ch3 H Cl 74 H OR4 ch3 F Cl 75 H OR4 ch3 Cl Cl 76 H OR4 ch3 ch3 Cl Modality C11. The process of any of the Modalities C1 to C10 where the reaction is carried out in a suitable solvent. C12 modality. The process of Modality C11 where the suitable solvent is methanol. Modality C13. The process of any one of Modes C1 through C12 where the reacting is carried out at a temperature at or below 0°C. Modality C14. The process of any of the Modalities C1 to C13 where the methoxylating agent is sodium methoxide. D. A process for preparing a compound of Formula 1-C D1 mode. A process as described in the Brief Description of the Invention for preparing a compound of Formula 1-C. D2 mode. The D1 Mode process where R1 is C1-C4 alkyl. D3 mode. The process of Mode D1 wherein R1 is C3-Ce cycloalkyl. D4 mode. The process of any one of Modes D1 through D3 where R2 is Cl or Br. D5 mode. The D4 Mode process where R2 is Cl. D6 mode. The process of any one of the Modalities D1 to D5 where R5 is H or CH3. D7 mode. The process of Mode D6 where R5 is H. D8 mode. The D6 Mode process where R5 is CH3. D9 mode. The process of any of the Modalities D1 to D8 where R6 is H. D10 modality. The process of Mode D1 wherein in the intermediate compound of Formula V, R1 is C1-C4 alkyl. D11 modality. The process of Modality D1 where in the intermediate compound of the Formula V, R1 is Cs-Ce cycloalkyl. D12 modality. The process of any one of Modes D10 through D11 wherein in the intermediate compound of Formula V, R5 is H or CH3. D13 modality. The process of Mode D12 where R5 is H. D14 modality. The process of Mode D12 where R5 is CH3. Modality D15. The process of one of any of the Modalities D10 to D14 where R6 is H. D16 modality. The process of one of any of the Modalities D10 to D14 where R6 is Cl. Modality D17. The process of any one of Modes D1 through D16 further comprises isolating the compound of Formula 1-C. Modality D18. The D1 Mode process wherein the compound of Formula 1-C is selected from the group consisting of Com. No. 33, 34, 35, 36, 37, 38, 39, 40, 41,42, 43, 44, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87 and 88 ( this is a compound of Formula I wherein R1 is CH3; R2 is Cl, Br, or I; R3 is OR4; R4 is CH3; R5 is H, F, Cl, or CH3; and R6 is H or Cl, as listed in TABLE DD). TABLE DD ncccnn / i 7Π7 / Β / Υ Com. No. R2 R3 R4 R5 R6 33 Cl OR4 CH3 H H 34 Cl OR4 ch3 F H 35 Cl OR4 CH3 Cl H 36 Cl OR4 CH3 CH3 H 37 Br OR4 CH3 H H 38 Br OR4 CH3 F H 39 Br OR4 CH3 Cl H 40 Br OR4 ch3 CHs H 41 I OR4 CH3 H H 42 I OR4 CH3 F H 43 I OR4 CH3 Cl H 44 I OR4 CH3 CH3 H 77 Cl OR4 CH3 H Cl 78 Cl OR4 CH3 F Cl 79 Cl OR4 CH3 Cl 80 Cl OR4 CH3 CH3 Cl 81 Br OR4 CH3 H Cl 82 Br OR4 CH3 F Cl 83 Br OR4 CH3 Cl Cl 84 Br OR4 CH3 CH3 Cl 85 I OR4 CH3 H Cl Com. No. R2 R3 R4 R5 R6 86 I OR4 CH3 F Cl 87 I OR4 CH3 Cl Cl 88 I OR4 ch3 CH3 Cl ncccnn / i ζηζ / Β / γ Modality D19. The process of any of the Modalities D1-D18 wherein reacting a compound of Formula 1-B with a tmp-zinc base is carried out in a suitable solvent. D20 mode. The process of Modality D19 where the suitable solvent is a tetrahydrofuran. Modality D21. The process of any one of Modes D1-D20 wherein the tmp-zinc base is an organometallic tmp-zinc base. D22 modality. The D21 Mode process where the tmp-zinc base is prepared from zinc chloride and 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex. Modality D23. The D22 Mode process where the tmp-zinc base is bis(2,2,6,6tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex. D24 modality. The process of any of the Modalities D1 to D22 where the reaction of the intermediate with a halogenating agent is carried out in a suitable solvent. D25 modality. The D24 Mode process where the suitable solvent is tetrahydrofuran. Modality D26. The process of any one of the Modalities D1 halogenating agent is iodine, / V-bromosuccinimide or isocyanuric chloride. Modality D27. The process of any one of the halogenating agent Modalities D1 is / V-bromosuccinimide or isocyanuric chloride. Modality D28. The process of any one of the Modalities D1 halogenating agent is isocyanuric chloride. Modality D29. The process of any one of the Modalities D1 to D25 where the to D26 where the to D27 where the to D28 where the compound of Formula 1-C where R 1 is C1-C4 alkyl or C3-C6 cycloalkyl; R2 is Cl; R5 is H, F, Cl or CH3; and R6 is H or Cl; comprises reacting a compound of Formula 1-E with a methoxylating agent. D30 mode. The D29 Mode process where the methoxylating agent is sodium methoxide. E. A process for preparing a compound of Formula 1-D E1 mode. A process as described in the Brief Description of the Invention for preparing a compound of Formula 1-D. E2 mode. The E1 Mode process where R1 is C1-C4 alkyl. E3 mode. The E1 Mode process where R1 is Cs-Ce cycloalkyl. E4 mode. The process of Modalities Ε1 or E2 where R1 is CH3. E5 mode. The process of one of any of the Modalities E1 to E4 where R2 is Cl. E6 mode. The process of any one of the Modalities E1 to E4 where R2 is Br. E7 mode. The process of one of any of the Modalities E1 to E4 where R2 is I. E8 mode. The process of one of any of the Modalities E1 to E7 where R5 is H. E9 mode. The process of one of any of the Modalities E1 to E7 where R5 is F. ncccnn / i ζπζ / β / υ E10 modality. The process of one of any of the Modalities E1 to E7 where R5 is Cl. Modality E11. The process of one of any of the Modalities E1 to E7 where R5 is CH3. E12 mode. The process of one of any of the Modalities E1 to E11 where R6 is H. Modality E13. The process of one of any of the Modalities E1 to E11 where R6 is Cl. Modality E14. The E1 Mode process wherein the compound of Formula 1-B is selected from the group consisting of Comp. No. 20, 21,22, 23, 24, 25, 26, 27, 28, 65, 66, 67, 68, 69, 70, 71 and 72 (this is a compound of Formula I where R1 is CH3; R2 is Cl, Br, or I; R3 is OR4; R4 is H; R5 is H, F, Cl, or CH3; and R6 is H or Cl, as listed in TABLE EE). TABLE EE Com. No. R2 R3 R4 R5 R6 21 Cl OR4 H F H 22 Cl OR4 H Cl H 20 Cl OR4 H ch3 H 23 Br OR4 H F H 24 Br OR4 H Cl H 25 Br OR4 H ch3 H 26 I OR4 H F H 27 I OR4 H Cl H 28 I OR4 H ch3 H 65 Cl OR4 H H Cl 66 Cl OR4 H F Cl 67 Cl OR4 H Cl Cl 68 Cl OR4 H ch3 Cl 69 I OR4 H H Cl Com. No. R2 R3 R4 R5 R6 70 I OR4 H F Cl 71 I OR4 H Cl Cl 72 I OR4 H ch3 Cl ncccnn / i ζηζ / Β / γ Modality E15. The process of any one of Modes E1 through E13, wherein the reacting is carried out in a suitable solvent. Modality E16. The process of Mode E14, where the reacting is carried out in a liquid demethylating agent in the absence of an additional solvent. Modality E17. The process of one of any of the Modalities E2 up E15 where reacting is performed at a temperature at or above 80°C. Modality E18. The process of one of any of the Modalities E1 up E16 where the demethylating agent is morpholine. Modality E18. The process of one of any of the Modalities E1 up E16 where the demethylating agent is other than morpholine. F. A process for preparing a compound of Formula 1-E F1 mode. A process as described in the Brief Description of the preparation of a compound of Formula 1-E. invention for F2 mode. The process of Mode F1 where R1 is C1-C4 alkyl. F3 mode. The process of Mode F1 wherein R1 is C3-C6 cycloalkyl. F4 mode. The process of Modalities F1 to F2, where R1 is CH3. h. F. Cl. CH3. F5 mode. He F6 mode. He F7 mode. He F8 mode. He F9 mode. The process process process process process of of of of one of one one of any of the Modalities F1 of any of the Modalities F1 of any of the Modalities F1 of any of the Modalities F1 of any of the Modalities F1 to F4 to F4 to F4 to F4 to F8 in in in in where R5where R5where R5where R5where R6is is is is h. F10 mode. The process of one of any of the Modalities F1 to F8 where R6 is Cl. F11 mode. The F1 Mode process, wherein the compound of Formula 1-E is selected from the group consisting of Comp. No. 5, 6, 7 and 8 (this is a compound of Formula I wherein R1 is CH3; R2 is Cl; R3 is Cl; R4 is not present (that is --); R5 is H, F, Cl or CH3; and R6 is H o Cl, as listed in TABLE FF). TABLE FF Com. No. R2 R3 R4 R5 RB 5 Cl Cl — H H 6 Cl Cl — F H 7 Cl Cl — Cl H 8 Cl Cl __ ch3 H ncccnn / i ζηζ / Β / γ F12 mode. The process of any one of Modes F1 through F11, wherein the reacting is performed in a suitable solvent. F13 mode. The process of Modality F12, where the suitable solvent is toluene. G. An Alternative Process to Prepare a Compound of Formula 1-E G1 mode. A process as described in the Brief Description of the Invention for preparing a compound of Formula 1-E. G2 mode. The process of Mode G1 where R1 is C1-C4 alkyl. G3 mode. The process of one of any of the Modalities G1 to G2 where R1 is CH3. G4 mode. The process of one of any of the Modalities G1 to G3 where R5 is F. G5 mode. The process of any one of Modality G1 to G3 where R5 is Cl. G6 mode. The process of any one of Modality G1 to G3 where R5 is CHE. G7 mode. The process of one of any of the Modalities G1 to G3 where R5 is H. G8 mode. The process of one of any of the Modalities G1 to G7 where R6 is H. G9 mode. The process of one of any of the Modalities G1 to G7 where R6 is Cl. G13 mode. The process of Mode G1, wherein the compound of Formula 1-E is selected from the group consisting of Comp. No. 5, 6, 7, and 8 (this is a compound of Formula I wherein R1 is CH3; R2 is Cl; R3 is OR4; R4 is H; R5 is H, F, Cl, or CH3; and R6 is H or Cl, as listed above in TABLE FF). G14 mode. The process of any one of Modalities G1 to G13 wherein a compound of Formulas II or III are as described in the Brief Description of the Invention. G15 mode. The process of Modality G14 where R5 is F. G16 mode. The process of Modality G14 where R5 is Cl. G17 mode. The process of Modality G14 where R5esCH G18 mode. The process of Modality G14 where R5 is H. G19 mode. The process of one of any of the Modalities G14 to G18 where R6 is H. G20 mode. The process of one of any of the Modalities G14 to G18 where R6 is Cl. G21 mode. The process of any one of the Modalities G1 to G20 where in a compound of Formula 7 is as defined in the Brief Description of the Invention. G22 mode. The process of Mode G20 where R1 is C1-C4 alkyl. G23 mode. The process of Mode G20 where R1 is Cs-Ce cycloalkyl. G24 mode. The process of Mode G22 where R1 is CH3. G25 mode. The process of any one of Modalities G1 through G24 further comprises isolating the compound of Formula 1-E. G26 mode. The process of any one of Modalities G1 to G25, wherein the reacting of a compound of Formula II with magnesium is carried out in a suitable solvent. G27 mode. The process of Embodiment G26, wherein the reacting of a compound of Formula II with magnesium is carried out in tetrahydrofuran. G28 mode. The process of any of Modalities G1 to G27, wherein the reacting of a compound of Formula II with magnesium is carried out at a temperature above 80°C. G29 mode. The process of any one of Modes G1 through G28, wherein the reacting is performed at a temperature at or below 0°C. The invention also relates to a method of controlling unwanted vegetation comprising applying herbicidally effective amounts of the compounds of the invention to the locus of vegetation (eg, as a composition described herein). It should be noted that the embodiments relating to methods of use are those involving the compounds of embodiments described above. Compounds of the invention are particularly useful for the selective control of weeds in crops such as wheat, barley, corn, soybean, sunflower, cotton, rapeseed, and rice, and specialty crops such as sugarcane, citrus, fruit, and nut crops. Also noteworthy as modalities are the herbicidal compositions of the present invention comprising the compounds of modalities described above. The invention also includes a herbicide mixture comprising (a) a compound selected from Formula 1, / V-oxides, and salts thereof, and (b) at least one additional active ingredient selected from (b1) photosystem inhibitors II, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3) acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5) 5-enol-pyruvilsh¡kimate-3 synthase mimics -phosphate (EPSP), (b6) photosystem I electron deflectors, (b7) protoporphyrinogen oxidase (PPG) inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) fatty acid chain elongase inhibitors very long (VLCFA), (b10) auxin transport inhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12) 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, (b13) solenesyltransererase homogentisate inhibitors ( HST), (b14) cellulose biosynthesis inhibitors, (b15) other herbicides including mitotic disruptors, organic arsenicals, asulam, bromobutide, cinmethylin, cumyluron, dazomet, difenzoquat, ncccnn / i ζπζ / β / υ dymron, etobenzanid , flurenol, fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16) herbicide protectants; and salts of compounds from (b1) to (b16). "Photosystem II inhibitors" (b1) are chemical compounds that bind to the D-1 protein in the Qb-binding niche and thus block electron transport from Qa to Qb in chloroplast thylakoid membranes. Electrons blocked from passing through photosystem II are transferred through a series of reactions to form toxic compounds that disrupt cell membranes and cause chloroplast swelling, membrane leakage, and ultimately cell destruction. The Qb binding niche has three different binding sites: the A binding site binds triazines such as atrazine, triazinones such as hexazinone, and uracils such as bromacil, the B binding site binds phenylureas such as diuron, and the binding site C binds benzothiadiazoles such as bentazon, nitriles such as bromoxynil, and phenyl-pyridazines such as pyridate. Examples of photosystem II inhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil, bromophenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, cloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn, dimefuron, dimethamethrin, diuron, etidimuron, fenuron, flu ometuron , hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron, metabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, promethrin, propanil, propazine, pyridafol, pyridate, siduron, simazine, simethrin, tebuthiu ron , terbacil, terbumeton, terbutylazine, terbutrin and triethazine. "AHAS inhibitors" (b2) are chemical compounds that inhibit acetohydroxy acid synthase (AHAS), also known as acetolactate synthase (ALS), and thus kill plants by inhibiting the production of branched-chain aliphatic amino acids such as valine, leucine and isoleucine, which are required for protein synthesis and cell growth. Examples of AHAS inhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chloransulam-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flumetsulam, flupyrsulfuron -methyl, flupyrsulfuron-sodium, foramsulfuron, halosulfuronmethyl, imazametabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron-methyl (including sodium salt), iofensulfuron (2-iodo- / V-[[( 4-methoxy-6-methyl-1,3,5-triazin-2yl)amino]carbonyl]benzenesulfonamide), mesosulfuron-methyl, metazosulfuron (3-chloro-4-(5,6-dihydro-5methyl-1, 4,2-dioxazin-3-yl)- / \ / -[[(4,6-dimethoxy-2-p¡r¡m¡n¡l)am¡no]carbon¡l]-1 -methyl-1 / 7-pyrazole-5-sulfonamide), metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron (2-chloro- / V-[ [(4,6-dimethoxy¡-2-pyrimidin¡l)amino]carbon¡l]-6propylimidazo[1,2-jb]pyr¡daz¡na-3-sulfonam¡de), prosulfuron, pyrazosulfuron -ethyl, pyribenzoxim, pyriphthalid, pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thifensulfuron-methyl, triafamone (A / -[2-[(4,6-dimethoxy-1,3,5 -triazin-2-¡l)carbon¡l]-6-fluorophenyl]-1,1 -difluoro- / \ / methylmethanesulfonamide), triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodium salt), triflusulfuron -methyl and tritosulfuron. "ACCase inhibitors" (b3) are chemical compounds that inhibit the enzyme acetyl-CoA ncccnn / i 7Π7 / Ε / Υ carboxylase, which is responsible for catalyzing an early step in the synthesis of lipids and fatty acids in plants. Lipids are essential components of cell membranes, and without them, new cells cannot be produced. The inhibition of acetyl CoA carboxylase and the subsequent lack of lipid production leads to losses in cell membrane integrity, especially in regions of active growth such as meristems. Eventually, shoot and rhizome growth ceases, and shoot meristems and rhizome buds begin to die. Examples of ACCase inhibitors include alloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop, diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim, and tralkoxydim, including resolved forms such as fenoxaprop- P, fluazifop -P, haloxyfop-P and quizalofop-P and ester forms such as clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl. Auxin is a plant hormone that regulates growth in many plant tissues. “Auxin mimics (b4) are chemical compounds that mimic the plant growth hormone auxin, thereby causing uncontrolled and disorganized growth leading to plant death in susceptible species. Examples of auxin mimics include aminocyclopyrachlor (6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and its methyl and ethyl esters and their sodium and potassium salts, aminopyralid, benazolin-ethyl, chloramben, clacifos, clomeprop, clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen (4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylic acid), halauxifen-methyl (methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate), MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3 ,6-TBA, triclopyr, and methyl 4-amino-3chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pindincarboxylate. "EPSP synthase inhibitors" (b5) are chemical compounds that inhibit the enzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in the synthesis of aromatic amino acids such as tyrosine, tryptophan and phenylalanine. EPSP inhibitor herbicides are readily absorbed through the foliage of plants and are carried in the phloem to growing points. Glyphosate is a relatively non-selective post-emergence herbicide that belongs to this group. Glyphosate includes esters and salts such as ammonium, isopropylammonium, potassium, sodium (including sesquisodium), and trimesium (alternatively called sulfosate). “Photosystem I electron deflectors” (b6) are chemical compounds that accept electrons from Photosystem I, and after several cycles, generate hydroxyl radicals. These radicals are extremely reactive and readily destroy unsaturated lipids, including membrane fatty acids and chlorophyll. This destroys the integrity of the cell membrane, so that the cells and organelles "leak", which leads to wilting and rapid desiccation of the leaves, and eventually death of the plants. Examples of this second type of photosynthesis inhibitor include diquat and paraquat. "PPO inhibitors" (b7) are chemical compounds that inhibit the enzyme protoporphyrinogen oxidase, rapidly resulting in the formation of highly reactive compounds in plants that rupture cell membranes, causing leakage of cell fluids. Examples of PPO inhibitors include acifluorfen-sysodium, azafenidin, benzfendizone, biphenox, butafenacil, carphantrazone, carphantzone ncccnn / i 7π7 / β / υ ethyl azin, fluorographic feet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone, tidiazimin, trifludimoxazin (dihydro-1,5dimethyl-6-thioxo-3-[2 ,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-11)-2 / - / -1,4-benzoxazin-6-yl]-1 ,3,5-triazine2,4(1 / - / ,3 / - / )-dione) and thiafenacil ( / V-[2-[[2-chloro-5-[3,6-d¡h¡dro- 3-methyl-2,6-d¡oxo-4-(trifluoromethyl)-1 (2 / - / )pyrimid¡n¡l]-4-fluorophenyl]thio]-1 -oxopropyl]-p-alaninate methyl). “GS inhibitors” (b8) are chemical compounds that inhibit the activity of the glutamine synthetase enzyme, which plants use to convert ammonia into glutamine. Consequently, ammonia accumulates and glutamine levels decrease. Plant damage is probably due to the combined effects of ammonia toxicity and deficiency of amino acids required for other metabolic processes. GS inhibitors include glufosinate and its esters and salts such as glufosinatoammonium and other phosphinothricin derivatives, glufosinate-P((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid), and bilanafos. "VLCFA elongase inhibitors" (b9) are herbicides having a wide variety of chemical structures, which inhibit elongase. Elongase is one of the enzymes located in or near chloroplasts that are involved in VLCFA biosynthesis. In plants, very long chain fatty acids are the main constituents of hydrophobic polymers that prevent desiccation on the leaf surface and provide stability to pollen grains. Such herbicides include acetochlor, alachlor, anilophos, butachlor, cafenstrol, dimethachlor, dimethenamide, diphenamide, phenoxasulfone (3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro -5,5-dimethylsoxazole), fentrazamide, flufenacet, indanofan, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, napropamide-M ((2R)- / V, / V-diethyl-2-(1 -naphthalenyloxy)propanamide), petoxamid, piperofos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor, which includes resolved forms such as S-metolachlor and chloroacetamides and oxyacetamides. "Auxin transport inhibitors" (b10) are chemicals that inhibit auxin transport in plants, such as by binding to an auxin transporter protein. Examples of auxin transport inhibitors include diflufenzopyr, naptalam (also known as N(1-naphthyl)phthalamic acid and 2-[(1-naphthalenylamino)carbonyl]benzoic acid). "PDS inhibitors" (b11) are chemical compounds that inhibit the carotenoid biosynthesis pathway at the phytoene desaturase stage. Examples of PDS inhibitors include beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurzon, and picolinafen. "HPPD inhibitors" (b12) are chemicals that inhibit the biosynthesis of 4-hydroxyphenyl-pyruvate dioxygenase synthesis. Examples of HPPD inhibitors include benzobicyclone, benzofenap, bicyclopyrone (4-h¡drox¡-3-[[2-[(2-methoxyethoxy¡)methyl]-6-(trifluoromethyl)-3-p¡ r¡d¡n¡l]carbon¡l]b¡c¡clo[3.2.1]oct-3en-2-one), phenquinotrione (2-[[8-chloro-3,4-dih¡dro-4 -(4-methox¡phenyl)-3-oxo-2-qu¡noxal¡n¡l]carbonyl]-1,3cyclohexanedione), isoxachlortole, isoxaflutole, mesotrione, pyrasulfotol, pyrazolinate, pyrazoxifene, sulcotrione, tefuryltrione, tembotrione , tolpyralate (1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4(methylsulfonyl)benzoyl]-1H-plrazol-5-yl]oxy]ethyl methyl carbonate), topramezone , 5-chloro-3-[(2-hydroxy-6-oxo-1 ncccnn / i 7Π7 / Β / Υ cyclohexen-1 -yl)carbonyl]-1 -(4-methoxyphenyl)-2(1H)-quinoxalinone , 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6dimethyl-3(2 / 7)-pyridazinone, 4-(4-fluorophenyl)- 6-[(2-hydroxy-6-oxo-1 -cyclohexen-1 -i I) ca rcarbon i l]-2-m ethyl-1,2,4triazine-3,5(2 / 7,4 / 7)- Dione, 5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3methoxypropyl)-4(3 / 7 )-pyrimidnone, 2-methyl- / V-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4(tnfluoromethyl)benzamide and 2-methyl -3-(methylsulfonyl)- / V-(1-methyl-1 / 7-tetrazol-5-yl)-4-(trifluoromethyl)benzamide. "HST inhibitors" (b13) alter a plant's ability to convert homogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thus altering carotenoid biosynthesis. Examples of HST inhibitors include cyclopyrimorate (6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl-4-morpholinecarboxylate), haloxydine, pyrichlor, 3-(2-chloro-3,6-difluorophenyl)-4- hydroxy-1-methyl-1,5-naphthyridin-2(1 / 7)-one, 7(3,5-d¡chloro-4-p¡nd¡n¡l)-5-(2,2-d ¡fluoroethyl)-8-hydroxy¡pyrido[2,3-b]pyraz¡n-6(5 / 7)-one and 4-(2,6-diethyl-4-methylphenyl) 5-Hydrox¡-2,6-dimethyl-3(2 / 7)-p¡ridaz¡none. HST inhibitors also include compounds of Formulas A and B. ncccnn / i 7Π7 / Β / Υ where Rd1 is H, Cl or CF3; Rd2 is H, Cl or Br; Rd3 is H or Cl; Rd4 is H, Cl or CF3; Rd5 is CH3, CH2CH3 or CH2CHF2; and RdSes OH, or -OC(=O)- / -Pr; and Re1 is H, F, Cl, CH3 or CH2CH3; Re2 is H or CF3; Re3 is H, CH3 or CH2CH3; Re4 is H, F or Br; Re5 is Cl, CH3, CF3, OCF3 or CH2CH3; Re6 is H, CH3, CH2CHF2 or C=CH; Re7 is OH, -OC(=O)Et, -OC(=O)- / -Pr or -OC(=O)-ABu; and Ae8 is N or CH. “Cellulose biosynthesis inhibitors” (b14) inhibit cellulose biosynthesis in certain plants. They are most effective when applied pre-emergence or post-emergence early on young or fast-growing plants. Examples of cellulose biosynthesis inhibitors include chlorthiamide, dichlobenil, flupoxam, indaziflam (Λ / 2-[(1 / ?,2S)-2,3-dihydro-2,6-dimethyl-1Hinden-1-yl] -6-(1 -fluoroethyl)-1,3,5-triaz¡na-2,4-d¡am¡na), isoxaben and triaziflam. “Other herbicides” (b15) include herbicides that act through a variety of different modes of action such as mitotic disruptors (for example, flamprop-M-methyl and flamprop-Misopropyl), organic arsenicals (for example, DSMA, and MSMA ), inhibitors of 7,8-dihydropteroate synthase, inhibitors of chloroplast isoprenoid synthesis, and inhibitors of cell wall biosynthesis. Other herbicides include those herbicides that have unknown modes of action or do not fall into a specific category listed in (b1) through (b14) or act through a combination of modes of action listed above. Examples of other herbicides include aclonifen, asulam, amitrol, bromobutide, cinmethylin, clomazone, cumiluron, daimuron, difenzoquat, etobenzanid, fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dimron, ipfencarbazone (1-(2,4-dichlorophenyl) / V-(2,4-difluorophenyl)-1,5-dihydro- / V-(1-methylethyl)-5-oxo-4 / - / -1,2,4-triazole-4-carboxamide ), metam, methyldimron, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb and 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5dihydro-5-methyl-3-( 3-methyl-2-thienyl)isoxazole. Other herbicides" (b15) also includes a compound of Formula (b15A) ncccnn / i ζηζ / Β / γ (b!5A) where R12 is H, Ci-Ce alkyl, Ci-Ce haloalkyl or C4-Cs cycloalkyl; R13 is H, O-Ce alkyl or Ci-Ce alkoxy; Q1 is an optionally substituted ring system selected from the group consisting of phenyl, thienyl, pyridinyl, benzodioxolyl, naphthyl, naphthalenyl, benzofuranyl, furanyl, benzothiophenyl, and pyrazolyl, wherein 1 to 3 R14 is substituted when substituted for such ring system; Q2 is an optionally substituted ring system selected from the group consisting of phenyl, pyridinyl, benzodioxolyl, pyridinonyl, thiadiazolyl, thiazolyl, and oxazolyl, wherein 1 to 3 R15 is substituted when such ring system is substituted; each R14 is independently halogen, Ci-Ce alkyl, Ci-Cb haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, Cs-Cs cycloalkyl, cyano, Ci-Cb alkylthio, Ci-Cb alkylsulfinyl, Ci-Ce alkylsulfonyl, SFs, NHR17 ; or phenyl optionally substituted by 1 to 3 R16; or pyrazolyl optionally substituted by 1 to 3 R16; each R15 is independently halogen, C1-C6 alkyl, O-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, cyano, nitro, Ci-Ce alkylthio, Ci-Ce alkylsulfinyl, Ci-Cb alkylsulfonyl; each R16 is independently halogen, Ci-Ce alkyl or Ci-Cb haloalkyl; R17 is C1-C4 alkoxycarbonyl. In an Embodiment where "other herbicides" (b15) also include a compound of Formula (b15A), it is preferred that R12 is H or Ci-Ce alkyl; more preferably R12 is H or methyl. Preferably R13 is H. Preferably Q1 is either a phenyl ring or a pyridinyl ring, each ring substituted by 1 to 3 R14; more preferably Q1 is a phenyl ring substituted by 1 to 2 R14. Preferably Q2 is a phenyl ring substituted by 1 to 3 R15; more preferably Q2 is a phenyl ring substituted by 1 to 2 R15. Preferably each R14 is independently halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkoxy; more preferably each R14 is independently chloro, fluoro, bromo, C1-C2 haloalkyl, C1-C2 haloalkoxy or C1-C2 alkoxy. Preferably each R15 is independently halogen, C1-C4 alkyl, C1-C3 haloalkoxy; more preferably each R15 is independently chloro, fluoro, bromo, C1-C2 haloalkyl, C1-C2 haloalkoxy or C1-C2 alkoxy. Specifically preferred "other herbicides" (b15) include one of any of the following ncccnn / i 7Π7 / Β / Υ (b15A-1) through (b15A-15): "Other herbicides" (b15) also includes a compound of Formula (b15B) (bl5B) where R18 is H, Ci-Ce alkyl, Ci-Ce haloalkyl or C4-Cs cycloalkyl; each R19 is independently halogen, O-Ce haloalkyl or Ci-Ce haloalkoxy; p is an integer of 0, 1, 2, or 3; each R20 is independently halogen, Ci-Ce haloalkyl or Ci-Cs haloalkoxy; and q is an integer of 0, 1,2, or 3. In an Embodiment where "other herbicides" (b15) also include a compound of Formula (b15B), it is preferred that R18 is H, methyl, ethyl or propyl; more preferably R18 is H or methyl; more preferably R18 is H. Preferably each R19 is independently chloro, fluoro, haloC1-C3alkyl or haloC1-C3alkoxy; more preferably each R19 is independently chloro, fluoro, C1 fluoroalkyl (ie fluoromethyl, difluoromethyl or trifluoromethyl) or C1 fluoroalkoxy (ie trifluoromethoxy, difluoromethoxy or fluoromethoxy). Preferably each R20 is independently chloro, fluoro, haloC1alkyl or haloC1alkoxy; more preferably each R20 is independently chloro, fluoro, fluoroC1alkyl (ie fluoromethyl, difluoromethyl or trifluoromethyl) or fluoroC1alkoxy (ie trifluoromethoxy, difluoromethoxy or fluoromethoxy). Specifically preferred "other herbicides" (b15) include one of any of the following (b15B-1) through (b15B-19): ncccnn / i 7Π7 / Β / Υ ncccnn / i ζπζ / β / υ ncccnn / i 7Π7 / β / υιλι ncccnn / i 7Π7 / β / υιλι “Herbicide protectants” (b16) are substances added to a herbicide formulation to eliminate or reduce the phytotoxic effects of the herbicide on certain crops. These compounds protect crops from herbicide damage but typically do not prevent the herbicide from controlling unwanted vegetation. Examples of herbicidal protectants include but are not limited to benoxacor, cloquintocetmexil, cumiluron, ciometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenchlorim, flurazole, fluxofenim, furilazole, isoxadiphen-ethyl, mefenpyr-diethyl, Mephenate, Methoxyphenone, Naphthalic Anhydride, Oxabethrinyl, / V-(aminocarbonyl)-2-methylbenzenesulfonamide and N(aminocarbonyl)-2-fluorobenzenesulfonamide, 1-bromo-4-[(chloromethyl)sulfonyl]benzene, 2-(dichloromethyl) -2methyl-1,3-dioxolane (MG 191), 4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660), 2,2-dichloro-1(2,2,5 -trimethyl-3-oxazolid¡n¡l)-ethanone and 2-methox¡-A / -[[4-[[(meth¡lam¡no)carbon¡l]am¡no]fen¡l ]sulfonyl]benzamide. Another embodiment where "other herbicides" (b15) also includes a compound of Formula (b15C), R1 (bl5C) where R1 is Cl, Br or CN; and R2 is C(=O)CH2CH2CF3, CH2CH2CH2CH2CF3, or 3-CHF2-isoxazol-5-yl. Specific examples include a compound of Formula (b15C) selected from (b15C1) 5-chloro2-[3-chloro-2-[3-(d¡fluoromethyl)-5-¡soxazol¡l]phenoxy]-p¡ r¡m¡d¡na y (b15C2) 1-[2-chloro-6-[(5-chloro-2p¡nm¡d¡nil)ox¡]fen¡l]-4,4,4-tr¡ fluoro-1-butanone. They are preferred for better control of unwanted vegetation (for example, slower rate of use such as higher effects than additives, broader spectrum of weeds controlled, or improved crop safety), or to prevent the development of resistant weeds. , mixtures of a compound of the invention with a herbicide selected from the group consisting of atrazine, azimsulfuron, beflubutamid, S-beflubutamid, benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl, chlorsulfuron-methyl, clomazone, clopyralid potassium, chloransulam-methyl , 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethyl-isoxazolidinone, 2-[(2,5-dichlorophenyl)methyl]-4,4-d¡methyl-¡ soxazol¡dinone, etamesulfuron-methyl, flumetsulam, 4-(4-fluorophenyl)-6-[(2-hydroxy¡-6-oxo-1-c¡clohexen-1-¡l)carbon¡l]-2 -methyl-1,2,4-triazine-3,5(2H,4 / - / )-dione, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr, lenacil, mesotrione, metribuzin, metsulfuron-methyl, petoxamid , picloram, pyroxasulfone, quinclorac, rimsulfuron, S-metolachlor, sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl, and tribenuron-methyl. A compound of Formula I (where R5 is H, F, Cl, or CH3) can be prepared by acidification of the corresponding morpholine salt of Formula I-M as described in Reaction Scheme 1. The reaction in Scheme of Reaction 1 typically involves the addition of the compound of Formula 1-M, either as a solid or as a slurry or as a solution, to an aqueous acid, such as hydrochloric acid or sulfuric acid. The solvent used for slurry of the Formula I-M compound is typically a water-miscible organic solvent such as methanol, ethanol, acetonitrile, tetrahydrofuran, Λ / , / V-dimethylformamide, and the like. The free acid form of Formula I is typically insoluble in the aqueous acid solution and is isolated by filtration. Alternatively, the free acid forms of a Formula I compound can be isolated by dividing the morpholine salt of a Formula I compound between an aqueous acid and a suitable, insoluble solvent such as dichloromethane, chloroform, or ethyl acetate. . ncccnn / i ζπζ / β / υ The compound of Formula 1-M can be prepared in two steps starting with compounds of Formula 2 (where R5 is H, F, Cl or CH3) as shown in Reaction Schemes 2 and 3. In Reaction Scheme 2, A compound of Formula 2 is reacted with sodium methoxide or potassium methoxide in a solvent such as dioxane, tetrahydrofuran, toluene, Λ / , / V-dimethylformanide, or methanol at a temperature ranging from 0°C to room temperature. reflux of the solvent. One to two molar equivalents of sodium methoxide or potassium methoxide are typically used. The product of Reaction Scheme 2 may contain a mixture of compounds of Formulas 3 and 4 (where R5 is H, F, Cl or CH3). This mixture can be used as shown in Reaction Scheme 3 without purification. Reaction Scheme 2 In Reaction Scheme 3, the mixture of a compound of Formulas 3 and 4 can be ncccnn / i 7Π7 / Β / Υ heated in morpholine at reflux temperatures whereupon the compound of Formula 3 forms the compound of Formula 1-M but a compound of Formula 4 is not reacted with morpholine. Reaction analysis consists of optionally removing excess morpholine under distillation or vacuum, followed by dilution with an organic solvent such as diethyl ether or ethyl acetate. The compound of Formula 1-M is typically insoluble in the solvent and can be isolated by filtration, while the Unreacted Formula 4 remains in solution and can be recovered from the filtrate. Reaction Scheme 3 (insoluble in diethyl ether) soluble in diethyl ether A compound of Formula 2 can be formed by heating compounds of Formula 4 in pyridine-containing phosphorous oxychloride as described in Reaction Scheme 4. Conditions for the reactions of Reaction Scheme 4 can be found in the Polish Journal of Chemistry, 1990, vol. 64, p. 741. A compound of Formula 4 can be converted to a compound of Formula 3 by chlorination followed by methoxylation as shown in Reaction Schemes 4 and 2. Reaction Scheme 4 ncccnn / i ζηζ / Β / γ A compound of Formula 2 (where R5 is H, F, Cl, or CH3) can be prepared by the reaction of a compound of Formula 5 with a Grignard reagent of Formula 6 as described in Reaction Scheme 5. The Reactions in Reaction Scheme 5 are typically carried out in a solvent such as tetrahydrofuran or diethyl ether at temperatures ranging from -78°C to the reflux temperature of the solvent, with -20°C to 25°C being most representative. . The Grignard reagent of Formula 6 where R5=H is commercially available while the Grignard reagent of Formula 6 where R5=CH3 can be prepared from 1-bromo-2,7-dimethylnaphthalene using procedures known to those skilled in the art ( see J. Am. Chem. Soc. 2008, vol. 130, p. 6848). A compound of Formula 2 (where R5 is H, F, Cl or CH3) may alternatively be prepared by the reaction of a compound of Formula 7 with a Grignard reagent of Formula 6 as described in Reaction Scheme 6. The reactions of Reaction Scheme 6 are typically carried out in a solvent such as tetrahydrofuran or diethyl ether at temperatures ranging from -78°C to the reflux temperature of the solvent, with -20°C to 25°C being more. representative. Reaction scheme 6 ncccnn / i 7Π7 / Β / Υ Br^Mg The present disclosure also relates to a method of controlling unwanted vegetation which comprises applying to the locus of vegetation a herbicidally effective amount of one or more compounds of Formula I (eg, as a composition described herein). Compounds of Formula I are particularly useful for the selective control of weeds in crops including, but not limited to, wheat, barley, corn, soybeans, sunflower, cotton, rapeseed, rice, and specialty crops such as sugarcane crops. , citrus, fruits and nuts. Also noteworthy as embodiments are the herbicidal compositions of the present disclosure comprising compounds of Formula I. The present disclosure also includes a herbicide mixture comprising (a) a compound selected from Formula I, / V-oxides, and salts thereof, and (b) at least one additional active ingredient. Without further details, it is believed that one skilled in the art, using the above description, can use the present description to its fullest extent. The following non-limiting Examples are illustrative of the description. The steps in the following Examples illustrate a procedure for each step in a general synthetic transformation, and the starting material for each step may not necessarily have been prepared by a particular preparative run whose procedure is described in other Examples or steps. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. 1H NMR spectra are reported in ppm downfield from tetramethylsilane in CDCh unless otherwise indicated; “s” means singlet, “d” means doublet, “t” means triplet, “q” means quartet, “m” means multiplet, “dd” means doublet of doublets, “dt” means doublet of triplets, and “br s ” means broad singlet. Mass spectra (MS) are reported as the molecular weight of the highest isotopically abundant parent ion (M+1) formed by the addition of H+ (molecular weight of 1) to the molecule, or (M-1) formed by the loss of H+ (molecular weight of 1) of the molecule, observed using liquid chromatography coupled to a mass spectrometer (LCMS) using any atmospheric pressure (AP+) chemical ionization where “amu” means unified atomic mass units. SUMMARY EXAMPLE 1 Preparation of 6-chloro-5-hydroxy-2-methyl-4-(2-methyl-1-naphthalene)-3(2 / - / )-pyridazinone Step A: Preparation of 5- chloro-2-methyl-4-(2-methyl-1-naphthalene)-3(2 / - / )-pyridazinone (Com. No. 1) Under a nitrogen atmosphere, magnesium (5.4 g, 0.22 mol) was placed in a clean, dry flask. A few iodine crystals were added to activate the magnesium. A solution of 1-bromo-2-methylnaphthalene (31.0 mL, 0.20 mol) in tetrahydrofuran (200 mL) was added dropwise to the magnesium. After 25 mL of the solution was added, the addition was stopped to allow a gradual, mild exotherm to occur. Once small gas bubbles were observed, the dropwise addition was continued at a rate to maintain a vigorous, controlled reaction. Near the end of the addition the reaction was heated externally to maintain a gentle reflux. The reaction was heated for one hour after the addition was complete. Grignard formation was monitored by HPLC of an aliquot quenched with 1N aqueous hydrochloric acid. The reaction was cooled to -55°C. A solution of 5-chloro-4-methoxy-2-methyl-3(2 / - / )-pyridazinone (34.9 g, 0.20 mol) in tetrahydrofuran (400 mL) was added slowly, while maintaining a reaction temperature below -40°C. After the addition was complete, the cooling bath was removed to allow the reaction to warm to room temperature. The reaction was stirred an additional hour and monitored for completion. Once complete, the reaction was cooled to 0 °C, quenched with 1 N aqueous hydrochloric acid (500 mL), and stirred for 18 h at room temperature. The reaction was extracted twice with dichloromethane. The extracts were combined, dried over MgSO4, filtered, and concentrated. The concentrate was triturated for 18h with hexanes. The resulting mixture was cooled with an ice-water bath, filtered, washed with cold hexanes, and dried in vacuo to give a beige solid (50.8 g, 88% yield). 1H NMR δ 7.90 (s, 1H), 7.85 (m, 2H), 7.40 (m, 3H), 7.30 (m, 1H), 3.87 (s, 3H), 2.29 (s, 3H). Step B: Preparation of 5-methoxy¡-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyr¡daz¡none (Com. No. 29) A 5-chloro-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone (this is the product obtained in step A, 50.8 g, 0.18 mol) in methanol (180 mL) was added sodium methoxide (25% by weight in methanol, 61 mL, 0.27 mol). The reaction was heated to the reflux temperature of the solvent. The reaction was monitored after 18h by 1H NMR indicating that the starting material was consumed. The reaction was cooled to 0°C, then water (500 mL) was added. The resulting mixture was filtered and dried in vacuo to give a beige solid (40.9 g, 81% yield). 1H NMR δ 7.90 (s, 1H), 7.80 (m, 2H), 7.40 (m, 4H), 3.85 (s, 3H), 3.66 (s, 3H), 2.28 (s, 3H). Step C: Preparation of 6-chloro-5-methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone (Com. No. 33) Step C-1: A solution of zinc chloride (2.9 M in 2-methyltetrahydrofuran, 28 mL, 0.10 mol) in a dry flask, under a nitrogen atmosphere, was cooled to 5°C. The 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex (1.0 M in tetrahydrofuran / toluene, 100 mL, 0.10 mol) was added slowly at a rate that limited the exotherm to 15°C. The mixture was then ncccnn / i znz / B / v allowed to warm to room temperature to give a clear 0.39 M solution of b¡s(2,2,6,6-tetramethylp¡per¡d¡na)z¡ complex nc, magnesium chloride, lithium chloride to be used in the next stage. Step C-2: A stirred solution of 5-methoxy-2-methyl-4-(2-methyl-1-naphthalene)-3(2 / - / )-pyridazinone (this is the product obtained in step B above, 14 g, 50 mmol) in dichloromethane (250 mL) cooled to -20°C. While maintaining the reaction temperature below -15°C, bis(2,2,6,6-tetramethylpiperidinejzinc, magnesium chloride, lithium chloride complex (0.39 M, 128 mL, 50 mmol) was slowly added, and stirred cold for 10 min Thin layer chromatography (ie TLC) of a k-quenched aliquot indicated that zincation was complete Freshly ground trichloroisocyanuric acid (17.4 g, 74.9 mmol) was added in one portion to the stirred reaction to -20 C. After a slight exotherm to 0 C, the reaction was cooled again to -20 C and stirred cold for 30 min. TLC analysis indicated that the reaction was complete. Aqueous hydrochloric acid 1 N (300 mL) was added to the cold reaction and stirred at room temperature for 20 min. The mixture was filtered through a short pad of Celite® diatomaceous earth filter aided with dichloromethane. The filtrate was extracted twice with dichloromethane. The extracts were combined, dried over MgSO4, filtered, concentrated on Celite® diatomaceous earth filter aided, and purified by medium pressure liquid chromatography ("MPLC'j, eluting with 20% ethyl acetate in hexanes to provide the desired product as a light beige solid (14.1 g, 89% yield). 1H NMR δ 7.85 (d, 2H), 7.45 (m, 4H), 3.79 (s, 3H), 3.25 (s, 3H), 2.33 (s, 3H). Step D: Preparation of 6-chloro-5-hidrox¡-2-methyl-4-(2-methyl-1-naphthalen¡l)-3(2 / - / )-pyr¡daz¡none A mixture of 6-chloro-5-methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone (14.1 g, 44.8 mmol) in morpholine (45 mL ) was heated at reflux for 1 h, followed by cooling to room temperature. The mixture was diluted with hexanes (45 mL), stirred for 18 h, and filtered. The filtered solids were dried on the filter funnel under a flow of nitrogen. The solids were transfected to a flask with 1 N aqueous hydrochloric acid (200 mL). The mixture was stirred for 3h. The solids were filtered and dried in vacuo to give a light beige solid (10.4 g, 77% yield). 1H NMR (DMSO-de) δ 10.89-11.27 (b, 1H), 7.95 (m, 2H), 7.40 (m, 4H), 3.64 (s, 3H), 2.20 (s, 3H). SUMMARY EXAMPLE 2 Alternative Preparation of 6-chloro-5-hydroxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone Step A: Preparation of 5-chloro-2-methyl-4 -(2-methyl-1-naphthalene)-3(2 / - / )-pyridazinone (Com. No. 1) To a solution of 1-bromo-2-methylnaphthalene (100 g, 452 mmol) in tetrahydrofuran (400 mL) was added magnesium turnings (21.7 g, 904 mmol) and iodine (20 mg). The reaction mixture was heated at 70 °C for 2 h during which time the color turned deep green, and vigorous reflux was observed. 5-Chloro-4methoxy¡-2-methyl-3(2 / 7)-pyr¡daz¡none (65 g, 373 mmol) in tetrahydrofuran (400 mL) was taken up in another round bottom flask, the above reaction mixture it was added at -100 °C and the reaction mixture was stirred at room temperature for 4 h. Analysis by TLC in 20% ethyl acetate in petroleum ether showed the completion of the reaction. The reaction mixture was then quenched with saturated NH4Cl solution and extracted with ethyl acetate twice. The combined organic layer was washed with water, brine and ncccnn / i 7Π7 / Β / Υ dried over Na2SO4. The solvent was evaporated to give the crude product. The crude compound was washed with petroleum ether to give 84 g (65.3% yield) of the title compound as an off-white solid. Step B: Preparation of 5-methoxy¡-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone (Com. No. 29) To a solution of 5-chloro-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2H)-pyridazinone (this is the compound obtained in step A, 500 g, 1.76 mol) in dioxane (5.0 L), 30% sodium methoxide in methanol (949 mL, 5.26 mol) was added at room temperature and the reaction mixture was stirred at 110 °C for 2 h. Analysis by TLC in 50% ethyl acetate / petroleum ether showed completion of the reaction. The reaction mixture was emptied into ice-water, quenched with saturated NH4Cl solution, and extracted with dichloromethane twice. The combined organic layer was washed with water, brine, and dried over Na2SO4. The solvent was evaporated to give a crude product which was washed with petroleum ether to give 449 g (91.2% yield) of the title compound as a solid. Step C: Preparation of 6-chloro-5-methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone (Com. No. 33) In a round bottom flask, ZnCb (194 g, 1.42 mol) was taken and 1 M 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex in tetrahydrofuran (2378 mL, 2.37 mol) was added and the reaction mixture stirred. at room temperature for 2 h. 5-Methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / 7)-pyridazinone (this is the product obtained in step B, 333 g, 1.18 mol) and 1,3-dichloro5,5-dimethylhydantoin (281 g, 1.42 mol) were added portionwise and the reaction mixture was stirred at room temperature for 16 h. Analysis by TLC in 30% ethyl acetate / petroleum ether showed completion of the reaction. The reaction mixture was poured into ice-water, quenched with saturated sodium bisulfite solution, and extracted with dichloromethane twice. The combined organic layers were washed with water, brine, and dried over Na2SO4. The solvent was evaporated to give crude product. The crude product was washed with diethyl ether / petroleum ether to provide 205 g (55% yield) of the title compound as a white solid. Step D: Preparation of 6-chloro-5-hydroxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone 6-Chloro-5-methoxy¡-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridaz¡none (this is the product obtained in step C , 410 g, 1.30 mol) in morpholine (1.2 L) was stirred at 120 °C for 2 h. analysis by TLC in 50% ethyl acetate / petroleum ether showed completion of the reaction. The reaction mixture was then evaporated, acidified with concentrated hydrochloric acid, and stirred for 1 h at room temperature. The reaction mixture was filtered, washed with excess water and dried in vacuo to give 290 g (74.3% yield) of the title compound as an off-white solid. SUMMARY EXAMPLE 3 Preparation of 6-chloro-4-(2,7-d¡methyl-1-naphthalen¡l)-5-hidrox¡-2-methyl-3(2 / - / )-pyr¡daz¡none (Com. No. 20): Step A. Preparation of 5-chloro-4-(2,7-dimethyl-1-naphthalene)-2-methyl-3(2 / - / )-pyr¡daz¡none (Comm. No. 4): Magnesium turnings (4.22 g, 173 mmol, partially crushed with a mortar and pestle before weighing) were charged to a 1 L 3-necked round bottom flask fitted with a ncccnn / i 7Π7 / Β / Υ funnel. addition, large magnetic stir bar, and a reflux condenser. The apparatus was heated with a heat gun while slowly stirring the magnesium under a flow of N2. After cooling, a small amount of iodine crystals (80 mg) was added, the mixture was briefly heated again (reddish-brown fumes observed), and then a 5 mL portion of 1-bromo-2 solution, 7-Dimethylnaphthalene (35.2 g, 0.15 mol) and tetrahydrofuran (80 mL) were added. The reaction mixture began to rapidly change color from reddish brown to light blue with bubbles. The solution of 1-bromo-2,7-dimethylnaphthalene and tetrahydrofuran was added slowly at such a rate as to maintain a smooth flow (total time ca. 30 min). The resulting mixture was diluted with 64 mL tetrahydrofuran, refluxed for 1 h, and then cooled to -40°C. A solution of 5-chloro-4-methoxy-2-methyl-3(2 / - / )pyridazinone (21.7 g, 124 mmol) and tetrahydrofuran (80 mL) was then added and the resulting solution stirred at room temperature for 14 h. The resulting mixture was cooled in ice / water and quenched with added saturated aqueous NH4Cl (100 mL) at <15°C. The resulting mixture was partitioned between ethyl acetate (1.2 L) and saturated aqueous NH4Cl (1L), the aqueous layer extracted with ethyl acetate (500 mL), and the combined organic layers washed with saturated NH4Cl, brine, dried with MgSO4 and concentrated to give 38.1 g (85%) of crude 5-chloro-4-(2,7-dimethyl-1-naphthalenyl)-2-methyl-3(2 / - / )-pyridazinone which was used in the next step without further purification. The crude product contained minor by-products, including 2,7-dimethylnaphthalene. An analytical sample was prepared by MPLC on a silica gel column eluting with 0-50% ethyl acetate in hexanes. 1H NMR (500 MHz) δ 7.95 (s, 1H), 7.79 (d, 1H), 7.74 (d, 1H), 7.35 (d, 1H), ca. 7.26 (dd, 1H), 7.03 (brs, 1H), 3.88 (s, 3H), 2.42 (s, 3H), 2.26 (s, 3H). Stage B. Preparation of 4-(2,7-dimethyl-1-naphthalene)-5-methoxy-2-methyl-3(2 / - / )-pyridazinone (Comm. No. 32): A solution of crude 5-chloro-4-(2,7-dimethyl-1-naphthalene)-2-methyl-3(2 / 7)-pyridazinone (this is the product obtained in the step A, 38.1 g, 12 8 mmol) from step A and dioxane (890 mL) was treated with NaOMe (25% soln in MeOH, 87 mL, 383 mmol). The resulting dark brown mixture was refluxed for 16 h, cooled, and concentrated to remove most of the dioxane. The resulting residue was partitioned between CH2CI2 and excess saturated aqueous NH4CI, the aqueous layer (pH~10) extracted with CH2CI2, and the combined organics washed with saturated NH4CI, brine, dried over MgSO4, and concentrated to give 57 g of a thick oily coffee mix. Trituration of the thick mixture with diethyl ether gave a beige solid which was isolated by filtration, washed with some diethyl ether and dried over the synthesized material to give 4-(2,7-dimethyl-1- naphthalenyl)-2-methyl-3(2 / - / )-pyridazinone as a beige solid (10.6 g, 28%). 1H NMR analysis showed desired product of high purity. The filtrate from the above was concentrated to give a dark brown oily residue which was triturated with ether and hexanes to give additional compound (2.2 g, 6%). 1H NMR (500 MHz) δ 7.92 (s, 1H), 7.73 (d, 1H), 7.71 (d, 1H), 7.32 (d, 1H), 7.22 (dd, 1H), 7.11 (br s, 1H), 3.87 (s, 3H), 3.70 (s, 3H), 2.41 (s, 3H), 2.26 (s, 3H). Step C. Preparation of 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)5-methoxy-2-methyl-3(2 / - / )-pyridazinone (Com. No. 36): ncccnn / i ζπζ / β / υ A solution of 4-(2,7-dimethyl-1-naphthalenyl)-5-methoxy-2-methyl-3(2 / 7)-pindazinone (this is the product obtained in step B, 27.2 g, 92 mmol) and CH2CI2 (646 mL) was cooled in an ice / acetone bath to -10°C. A solution of b¡s(2,2,6,6-tetramethylpiper¡d¡na)z¡nc complex, magnesium chloride, lithium chloride in tetrahydrofuran / 2-methyl tetrahydrofuran (231 mL of a solution 0.40 M ca., ca. 92 mmol) was added at <0°C. The resulting mixture was warmed to 18°C with a water bath, stirred 15 min, and then cooled to -15°C. 1,3-Dichloro-5,5-dimethylhydantoin (21.8 g, 111 mmol) was added portionwise to maintain <-10°C. The resulting mixture was warmed to room temperature and stirred for 7h. The resulting mixture was cooled to -10°C and quenched with sodium metabisulfite solution (50g) and water (250mL) added at <0°C. The resulting mixture was stirred rapidly as it warmed to room temperature for 1 h. The resulting mixture was diluted with CH2CI2 (600 mL) and water (300 mL), the aqueous layer was extracted with CH2CI2 (300 mL) and the combined organics washed with saturated aqueous ammonium chloride (2x500 mL), brine (300 mL ), dried with MgSO4 and concentrated to give 50 g of a brown oil. The crude product was purified by preparative MPLC on a 750 g column, eluting with 20-100% ethyl acetate in hexanes. The desired product 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-2-methyl-3(2 / 7)-pyridazinone was eluted first (11.2 g, 37% plus 3.3 g of slightly impure desired product in the first fraction). Further elution gave recovered unreacted 4-(2,7-dimethyl-1-naphthalenyl)-2-methyl-3(2 / - / )-pyridazinone (10.2 g, 38% recovery). 1H NMR (500 MHz) δ 7.78 (d, 1H), 7.73 (d, 1H), 7.32 (d, 1H), ca. 7.25 (dd, 1H), 7.15 (br s, 1H), 3.80 (s, 3H), 3.26 (s, 3H), 2.45 (s, 3H), 2.30 (s, 3H). Step D. Preparation of 6-chloro-4-(2,7-dimethyl-1-naphthalene)-5-hidrox¡-2-methyl-3(2 / 7)-pyridaz nona (Com. No. 20) A suspension of 6-chloro-4-(2,7-d¡m¡l-1-naphthalen¡l)-5-methoxy¡-2-methyl-3(2 / - / )-pyr¡daz¡none ( this is the product obtained in step C, 6.9 g, 21 mmol) and morpholine (21 mL) was heated under gentle reflux for 1 h, cooled to room temperature, and emptied into a mixture of concentrated hydrochloric acid (30 mL ) and ice (ca. 200 mL). The mixture was extracted with CH2CI2 (2 x 200 mL) and the combined organic layers washed with saturated NH4CI (2 x 100 mL), dried over MgSO4, and concentrated to give 6.0 g (91% yield) of the title compound as a light yellow solid, mp = 232-234°C. 1H NMR (500 MHz) δ 7.83 (d, 1H), 7.75 (d, 1H), 7.38 (d, 1H), 7.29 (dd, 1H), 7.13 (br s, 1H), 5.55 (vbrs, 1H), 3.83 (s, 3H), 2.44 (s, 3H), 2.28 (s, 3H). SUMMARY EXAMPLE 4 Alternative preparation of 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone (Com. No. 20): Step A: Preparation of 2,7-dimethylnaphthalene To a solution of 2,7-dibromonaphthalene (250 g, 0.877 mol) in dioxane (4 L) was added Pd(dppf)Cl2 and 2 M dimethyl zinc in toluene (2.19 L, 4.38 mol) at room temperature. The reaction mixture was stirred at 100°C for 16h. TLC analysis in hexane showed completion of the reaction. The reaction mixture was diluted with ethyl acetate and emptied into ice-water. The combined ncccnn / i 7Π7 / Β / Υ organic layer was washed with water, brine, and dried over sodium sulfate. The solvent was evaporated to give the crude product which was loaded onto a silica gel column. Elution from the column with petroleum ether gave 111 g (81% yield) of the title product as a white solid. Step B: Preparation of 1-bromo-2,7-dimethylnaphthalene To a solution of 2,7-dimethylnaphthalene (this is the product obtained in step A, 282 g, 1.8 mol) in CH3CN (2.8 L) and / V, / V-dimethylformamide (200 mL) was added / V- bromosuccinimide (321 g, 1.8 mol) and the reaction mixture was stirred at room temperature for 16 h. Analysis by TLC in hexane showed completion of the reaction. The reaction mixture was poured into ice-water and extracted with petroleum ether three times. The combined organic layer was washed with water, brine, and dried over Na2SO4. The solvent was evaporated to give the crude product which was purified by chromatography on silica gel eluting with petroleum ether to give 415 g (97% yield) of the title product as a pale yellow solid. Step C: Preparation of 5-chloro-4-(2,7-dimethyl-1-naphthalene)-2-methyl-3(2 / - / )-pyridazinone (Com. No. 4) To a solution of 1-bromo-2,7-dimethylnaphthalene (this is the product obtained in step B, 100 g, 0.42 mol) in tetrahydrofuran (500 mL) was added magnesium turnings (20.42 g, 0.851 mol) and iodine (20mg). The reaction mixture was heated at 70 °C for 2 h during which the color of the reaction mixture turned to deep green (vigorous reflux was observed). The Grignard reagent prepared above was added to a solution of 5-chloro-4-methoxy¡-2-methyl-3(2 / - / )-pyridazinone (61.1 g, 0.351 mol) in tetrahydrofuran (500 mL) and the mixture of reaction was stirred at room temperature for 4 h. TLC analysis in 20% ethyl acetate / petroleum ether showed completion of the reaction. The reaction mixture was quenched with saturated NH4Cl solution and extracted with ethyl acetate twice. The combined organic layer was washed with water, brine, and dried over NazSCu. The solvent was evaporated to give the crude product. The crude product was washed with petroleum ether to provide 82 g (64% yield) of the title compound as a white solid. Step D: Preparation of 4-(2,7-dimethyl-1-naphthalenyl)-5-methoxy-2-methyl-3(2 / - / )-pyridazinone (Com. No. 32) To a solution of 5-chloro-4-(2,7-dimethyl-1-naphthalene)-2-methyl-3(2H)-pyridazinone (this is the product obtained in the step C, 365 g, 1.2 mol) in dioxane (3.6 L), 30% NaOMe in methanol (661 mL, 3.6 mol) was added at room temperature and the reaction mixture was stirred at 110 °C for 2 h. Analysis by TLC in 50% ethyl acetate / petroleum ether showed completion of the reaction. The reaction mixture was emptied into ice-water, quenched with saturated NH4Cl solution, and extracted with dichloromethane twice. The combined organic layer was washed with water, brine, and dried over Na2SO4. The solvent was evaporated to give the crude product. The crude product was washed with petroleum ether to give 355 g (98% yield) of the pure title product as an off-white solid. Step E: Preparation of 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-methoxy-2-methyl-3(2 / - / )-pyridazinone (Com. No. 36) In a round bottom flask, ZnCI2 (65 g, 0.47 mol and 1 M 2,2,6,6-tetramethylpiperidinyl MgCI2L¡CI in tetrahydrofuran (952 mL, 0.952 mol) was added and the reaction mixture was stirred at ncccnn / i ζηζ / Β / γ room temperature for 2 h 4-(2,7-Dimethyl-1-naphthalenyl)-5-methoxy-2-methyl-3(2 / - / )-pyridazinone (this is the product obtained in step D, 140 g, 0.476 mol) and 1,3-dichloro-5,5-dimethylhydantoin (112 g, 0.571 mol) were added portionwise and the reaction mixture was stirred at room temperature for 16 h. TLC analysis in 30% ethyl acetate / petroleum ether showed completion of the reaction.The reaction mixture was emptied into ice-water, quenched with saturated sodium bisulfite solution, and extracted with dichloromethane twice.The organic layer Combined was washed with water, brine and dried over Na2SO4.The solvent was evaporated to give the crude product.The crude compound was washed with diethyl ether / petroleum ether to give 82 g (52% yield) as a white solid opaque. Step F: 6-chloro-4-(2,7-dimethyl-1-naphthalen¡l)-5-hidrox¡-2-methyl-3(2 / - / )-pyr¡daz¡ none (Comm. No. 20) 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-methoxy-2-methyl-3(2 / - / )-pyridazinone (this is the product obtained in step E, 208 g, 0.634 mol) in morpholine (650 mL) was stirred at 120°C for 2 h. TLC analysis in 50% ethyl acetate / petroleum ether showed completion of the reaction. The reaction mixture was evaporated, acidified with concentrated hydrochloric acid and stirred for 1h at room temperature during which time the solid precipitated. The solid was filtered, washed with excess water and dried in vacuo to give 195 g (98% yield) of the title compound as an off-white solid. SUMMARY EXAMPLE 5 Preparation of 5-chloro-6-methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone Step A: Preparation of 6-am¡no-5-chloro-4-methoxy¡-2-methyl-3(2 / - / )-pyridaz¡none A solution of sodium methoxide in methanol (4.8 mL of a 4.4 M solution, 21.0 mmol) was added to a suspension of 6-amino-4,5-dichloro-2-methyl-3(2 / - / )-pyridazinone (3.70 g, 19.1 mmol) and dioxane (95 mL, anhydrous) with ice-water bath cooling. The resulting suspension was stirred at room temperature for 3 h, poured into saturated aqueous ammonium chloride solution (150 mL) and the resulting mixture was extracted with methylene chloride (150 mL). The aqueous layer was extracted two more times with methylene chloride. The combined organic extracts were dried over anhydrous MgSO4, filtered, and concentrated to give 3.45 g of the title compound as a yellow semi-solid. 1H NMR (500 MHz) δ 4.34 (br s, 2H), 4.29 (s, 3H), 3.60 (s, 3H). Step B: Preparation of 5,6-dichloro-4-methoxy¡-2-methyl-3(2H)-pyridazinone To a solution of 6-amino-5-chloro-4-methox¡-2-methyl-3(2 / - / )-pyridazinone (this is the product obtained in step A, 529 mg, 2.8 mmol), copper(II) chloride (618 mg, 4.6 mmol), and acetonitrile (8 mL, anhydrous), tert-butyl nitrite (0.48 mL, 90% by weight, 3.6 mmol) was added with cooling by a water bath. water with ice. The resulting mixture was stirred at room temperature for 1 h, then partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic layer was washed with saturated aqueous ammonium chloride solution, dried over anhydrous MgSO4, filtered, and concentrated to give 0.51 g of the title compound as a yellow semi-solid. 1H NMR (500 MHz) δ 4.33 (s, 3H), 3.74 (s, 3H). Step C: Preparation of 5,6-dichloro-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone (Com. No. 5) 5,6-Dichloro-4-methoxy-2-methyl-3(2 / - / )-pyridazinone (this is the product obtained in step B, 0.41 g, 1.9 mmol) was added to 2-methyl-1 bromide -naphthalenyl-magnes¡o (9.0 mL of a solution in ncccnn / i znz / B / v tetra h id break n o 0.25 M, 2.3 mmol) at -20°C. The resulting mixture was stirred at room temperature for 30 min, at which time the reaction was cooled to 5 °C and quenched with saturated aqueous ammonium chloride solution (3 mL). The resulting mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution, the resulting organic layer was washed with saturated aqueous ammonium chloride solution, dried over anhydrous MgSO4, filtered, and concentrated to give 0.69 g of the title compound in crude form which was used in the next step without further purification. An analytical sample was prepared by MPLC purification on a silica column, eluting with a gradient of 0% to 100% ethyl acetate in hexanes. 1H NMR (500 MHz) δ 7.87-7.85 (m, 2H), 7.47-7.40 (m, 3H), 7.30-7.27 (m, 1H), 3.86 (s, 3H), 2.29 (s, 3H). Stage D. Preparation of 6-Chloro-5-methoxy¡-2-methyl-4-(2-methyl-1-naphthalen¡l)-3(2 / - / )-pyridaz¡none (Com. No. 33) Solid potassium methoxide (0.29 g, 3.4 mmol) was added to a solution of 5,6-dichloro-2-methyl4-(2-methyl-1-naphthalenyl)-3(2 / 7)-pyridazinone (this is the product obtained in step C, 0.69 g of crude product, ~1.7 mmol) and toluene (17 mL) at room temperature. The resulting mixture was stirred at room temperature for 3 d, cooled in an ice-water bath, and quenched with saturated aqueous ammonium chloride solution (10 mL). The resulting mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The organic layer was dried over anhydrous MgSO4, filtered and concentrated to give 0.60 g of the title compound in crude form, which was used in the next step without further purification. 1H NMR analysis of the crude product indicated a mixture of the desired product, 6-chloro-5-methoxy-2-methyl-4-(2-methyl-1-naphthalene)-3(2 / - / )-p ¡ridaz¡none, the isomer, 5-chloro-6-methoxy-2-methyl-4(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridaz¡none, and Unreacted 5,6-dichloro-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-p¡ndazinone in a ratio of 3.0:1.0:2.8, respectively. Analytical samples were obtained by MPLC on silica, eluting with a gradient of 0% to 100% ethyl acetate in hexanes. 6-Chloro-5-methoxy¡-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridaz¡none: 1H NMR (500 MHz) δ 7.84 (distorted d, 2H), 7.47-7.38 (m, 4H), 3.80 (s, 3H), 3.26 (s, 3H), 2.33 (s, 3H). 5-Chloro-6-methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone: 1H NMR (500 MHz) δ 7.86-7.83 (m, 2H), 7.45-7.37 (m, 3H), 7.33-7.30 (m, 1H), 4.01 (s, 3H), 3.77 (s, 3H), 2.29 ( s, 3H). SUMMARY EXAMPLE 6 Step A. Preparation of 6-chloro-5-hydroxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )-pyridazinone A solution of morpholine (2 mL) and the crude product of synthesis EXAMPLE 5, step D (0.60 g), which contains a mixture of 6-chloro-5-methoxy¡-2-methyl-4-(2-methyl- 1-naphthalenyl)-3(2 / 7)-pyridazinone, 5chloro-6-methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)-3(2 / - / )- pyridazinone and 5,6-dichloro-2-methyl-4-(2-methyl-1naphthalenyl)-3(2 / 7)-pyridazinone, was heated at 110°C for 2 h. The resulting mixture was concentrated and the residue was triturated with diethyl ether. The resulting solid was filtered, washed with diethyl ether, and dried over the synthesized material to give 6-chloro-5-hydroxy-2-methyl-4-(2-methyl-1-naphthalene) morpholine salt. ) ncccnn / i ζηζ / Β / γ 3(2 / - / )-pyridazinone. The filtrate contained unreacted 5-chloro-6-methoxy-2-methyl-4-(2-methyl-1-naphthalenyl)3(2 / - / )-pyridazinone and 5,6-dichloro-2-methyl- 4-(2-methyl-1-naphthalene)-3(2 / - / )-pyridazinone. The solid morpholine 6-chloro-5-hydrox¡-2-methyl-4-(2-methyl-1-naphthalen¡l)-3(2 / - / )-pyridaz¡none salt is partially dissolved in a minimal amount of tetrahydrofuran and the resulting mixture was gradually added to 1N aqueous hydrochloric acid (10 mL) with stirring. The resulting solid was isolated by filtration, washed with 1N aqueous hydrochloric acid, and dried over the synthesized material to give 200 mg of the title product as an off-white solid. 1H NMR (500 MHz) δ 7.92-7.86 (m, 2H), 7.48-7.40 (m, 6H), 3.83 (s, 3H), 2.33 (s, 3H). A compound of Formula I will generally be used as a herbicidal active ingredient in a composition, ie formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. In certain embodiments, the additional component can serve as a carrier. Formulation or composition ingredients are selected according to the physical properties of the active ingredient, mode of application and environmental factors such as soil type, humidity and temperature. Useful formulations include both liquid and solid compositions comprising the compound of Formula I. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates, and / or suspoemulsions) and the like, which can optionally be thickened into gels. General types of aqueous liquid compositions are soluble concentrates, suspension concentrate, capsule suspension, emulsion concentrate, microemulsion, oil-in-water emulsion, flowable concentrate, and suspo-emulsion. General types of non-aqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate, and oil dispersion. General types of solid compositions are dusts, powders, granules, pellets, granulated particles, tablets, tablets, filled films (including seed coatings), and the like, which may be water-dispersible ("wettable") or soluble. in water. Films and coatings formed from film-forming solutions or fluid suspensions are particularly useful for seed treatment. The active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire active ingredient formulation can be encapsulated (or "coated"). The encapsulation may control or delay the release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High strength compositions are used primarily as intermediates for further formulation. Sprayable formulations are typically spread in a suitable medium prior to spraying. Such liquid and solid formulations are formulated to be easily diluted in the spray medium, generally water, but occasionally another suitable medium such as an aromatic or paraffinic hydrocarbon or vegetable oil. Spray Volumes can range from about one to several thousand liters per hectare, but more typically are in the range of about ten to several hundred liters per hectare. The sprayable formulations can be tank-mixed with water or other suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be measured directly into drip irrigation systems or measured in the furrow during planting. Formulations will typically contain effective amounts of active ingredient, diluent, and surfactant within the following approximate ranges that add up to 100 percent by weight. ncccnn / i ζηζ / Β / γ Percent by Weight Active Ingredient Diluent Surfactant Granules, Tablets and Powders 0.001-90 0-99.999 0-15 Water Dispersible and Water Soluble Dispersion in Oils, Suspensions, Emulsions, Solutions (including Emulsifiable Concentrates) 1-50 40-99 0 -50 Powders 1-25 70-99 0-5 Granules and Pellets 0.001-99 5-99.999 0-15 High Strength Compositions 90-99 0-10 0-2 Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (for example, lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Liquid diluents include, for example, water, / V, / V-dimethylalkanamides (for example, N,Ndimethylformamide), limonene, dimethyl sulfoxide, / V-alkylpyrrolidones (for example, / V-methylpyrrolidinone), phosphates of alkyl (for example, triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (for example, white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerin, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, and alcohols, which they can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically CeC22), such as plant seed and fruit oils (for example, olive, castor, linseed, sesame, grain (corn), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut, and palm kernel), animal fats (for example, beef tallow, pork tallow, lard, cod liver oil, oil fish), and mixtures thereof. Liquid diluents also include alkylated (eg, methylated, ethylated, butylated) fatty acids, wherein the fatty acids can be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. The solid and liquid compositions of the present disclosure often include one or more surfactants. When added to a liquid, surfactants (also known as "surfactants") usually modify, more often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants may be useful as wetting, dispersing, emulsifying, or antifoaming agents. Surfactants can be classified as nonionic, anionic, or cationic. Useful nonionic surfactants for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and preparations from the alcohols and ethylene oxide, propylene, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers made from ethylene oxide or propylene oxide and reverse block polymers where the end blocks are made from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd clove (polyethylene glycol) resins, graft or comb polymers, and star polymers; polyethylene glycols (cloves); polyethylene glycol fatty acid esters; silicone based surfactants; and sugar derivatives such as sucrose esters, alkyl polyglycosides, and alkyl polysaccharides. Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and ncccnn / i 7Π7 / Β / Υ lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as alcohol alkoxylate phosphate esters, alkylphenol alkoxylate phosphate esters and styryl phenol ethoxylate phosphate esters; protein based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulphates and sulphonates of oils and fatty acids; ethoxylated alkylphenol sulfate sulfonates; alcohol sulfates; ethoxylated alcohol sulfates; amine and amide sulfonates such as / V, / V-alkyltaurates; sulfonates of benzene, eumene, toluene, xylene, and dodecyl and tridecylbenzenes; condensed naphthalene sulfonates; naphthalene and alkyl naphthalene sulfonates; fractionated petroleum sulfonates; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts. Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as / V-alkyl propanediamines, tripropylene triamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides. Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, Anionic, and Cationic Surfactants and their recommended uses are described in a variety of published references including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987. The compositions of this disclosure may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents, or surfactants). Such formulation auxiliaries and additives can control: pH (buffers), foaming during processing (defoamers such as polyorganosiloxanes), settling of active ingredients (suspending agents), viscosity (thixotropic thickeners), microbial growth in the container (antimicrobials ), product freezing (antifreeze), color (dye / pigment dispersions), washout period (film formers or self-adhesives), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers, and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon's Volume 2: Functional Materials, International and North American annual editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03 / 024222. The compound of Formula I and any other active ingredients are typically incorporated ncccnn / i 7Π7 / Β / Υ into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is insoluble in water, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Thick active ingredient mixtures with particle diameters up to 2,000 µm can be wet-milled using media mills to obtain particles with average diameters below 3 µm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations generally require dry milling processes, which produce average particle diameters in the range of 2 to 10 pm. Dusts and powders can be prepared by mixing and generally grinding (such as with a hammer mill or fluid energy mill). Granules and pellets can be prepared by spraying the active material onto preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 et seq., and WO 91 / 13546 . Pellets can be prepared as described in U.S. 4,172,714. The water dispersible and water soluble granules can be prepared as taught in the U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in the U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566. For additional information regarding formulation technique, see T. S. Woods, “The Formulator's Toolbox - Product Forms for Modern Agriculture” in Pesticide Chemistry and Blosclence, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings. of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. 3,309,192, Col. 5, line 43 to Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182 ; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000. In the following Examples, all percentages are by weight and all formulations are prepared in the conventional manner. The compound number, this is “Com. No." refers to the compounds in Table 1. Without further details, it is believed that one skilled in the art using the above disclosure can utilize the present disclosure to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting the description in any way. Percentages are by weight except where otherwise indicated. Example A High Strength Concentrate ncccnn / i znz / B / v Com. No. 22 98.5% Silica Airgel 0.5% Synthetic Amorphous Fine Silica 1.0% Example B Wettable Powder Com. No. 22 65.0% Dodecylphenol Polyethylene Glycol Ether 2.0% Sodium Lignin Sulfonate 4.0% Sodium Silicoaluminate 6.0% Montmorillonite (calcined) 23.0% Example C Granule Com. No. 22 10.0% ncccnn / i ζπζ / β / υ Attapulgite Granules (Low Volatile Matter, 0.71 / 0.30 mm; U.S.S. 90.0% No. 25-50 Sieves) Example D extracted pellets Com. No. 22 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium / magnesium bentonite 59.0% Example E Concentrate that can be emulsified Com. No. 22 10.0% polyoxyethylene sorbitol hexoleate 20.0% fatty acid methyl ester Ce-Cw 70.0% Example F microemulsion Com. No. 22 5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0% Alkyl polyglycoside 30.0% glyceryl monooleate 15.0% Water 20.0% Example G suspension concentrate Com. No. 22 35% polyoxyethylene / polypropylene butyl block copolymer 4.0% stearic acid / polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone antifoam 0.1% 1,2-benzisothiazolin-3-one 0.1% Water 53.7% Example H emulsion in water Com. No.22 10.0% polyoxyethylene / polypropylene butyl block copolymer 4.0% stearic acid / polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0% silicone antifoam 0.1% 1,2-benzisothiazolin-3-one 0.1% petroleum-based aromatic hydrocarbon 20.0 Water 58.7% Example I dispersion in oil Com. No. 22 25% polyoxyethylene sorbitol hexaoleate 15% organically modified bentonite clay 2.5% fatty acid methyl ester 57.5% Also described are Examples A through I above, wherein Com. No. 22 is replaced with Com. No. 20, Com. No. 21 or Com. No. 65. The test results indicate that the certain compounds of Formula I are active preemergence and / or postemergence and / or regulators of plant growth. Formula I compounds usually show the greatest activity for post-emergence weed control (that is, applied after weed seedlings emerge from the soil) and pre-emergence weed control (that is, applied before weed seedlings emerge). weed seedlings emerge from the soil). Many of them have utility for broad-spectrum pre- and / or post-emergence weed control in areas where complete control of all vegetation is desired such as around fuel storage tanks, industrial storage areas, parking lots, drive-ins, airfields, along river banks, irrigation and other waterways, around billboards and highway and railway structures. Many of the compounds of this description, by virtue of selective metabolism in crops versus weeds, or by selective activity at the site of physiological inhibition in crops and weeds, or by selective placement on or within the environment of a mixed crop and weed , are useful for the selective control of grass and broadleaf weeds within a crop / weed mixture. One skilled in the art will recognize that the preferred combination of these selective factors within a compound or group of compounds can readily be determined by performing routine biological and / or biochemical assays. Compounds of Formula I may show tolerance to important agronomic crops including, but not limited to, alfalfa, barley, cotton, wheat, rapeseed, sugar beet, grain (corn), sorghum, soybean, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugar cane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea, and forests such as eucalyptus and conifers (eg, loblolly pine); and grass species (eg, Kentucky bluegrass, St. Augustine grass, Kentucky fescue, and Bermudagrass). The compounds of this disclosure can be used in or on crops genetically transformed or bred to incorporate resistance to herbicides, express proteins toxic to invertebrate pests (such as Bacillus thuringiensis toxin), and / or express other useful traits. Those skilled in the art will appreciate that not all compounds are equally effective against all weeds. Alternatively, the subject compounds are useful for modifying plant growth. As the compounds of the disclosure have activity (both pre-emergence and post-emergence herbicidal) to control unwanted vegetation by killing or injuring vegetation or reducing its growth, the compounds can be usefully applied by a variety of methods involving putting into contacting a herbicidally effective amount of a compound of the disclosure, or a composition comprising such a compound and at least one of a surfactant, a solid thinner or a liquid thinner, to foliage or other unwanted vegetation or to the environment of the unwanted vegetation such as the soil or water in which the unwanted vegetation is growing or surrounding the seed or other propagule of the unwanted vegetation. A herbicidally effective amount of a compound of Formula I is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this description is about 0.001 to 20 kg / ha with a preferred range of about 0.004 to 1 kg / ha. One skilled in the art can readily determine the herbicidally effective amount necessary for the desired level of weed control. In a common embodiment, a compound of Formula I is applied, typically in a formulated composition, to a locus comprising desired vegetation (eg, crops) and unwanted vegetation (eg, weeds), both of which may be seeds. , seedlings and / or larger plants, in contact with a growing medium (eg soil). Here, a composition comprising a compound of the disclosure can be applied directly to a plant or part thereof, particularly unwanted vegetation, and / or to the growth medium in contact with the plant. ncccnn / i 7Π7 / Β / Υ Plant varieties and cultivars of the desired vegetation on the site treated with a compound of the disclosure may be obtained by conventional propagation and breeding methods or by genetic engineering methods. Genetically modified plants (transgenic plants) are those in which a heterologous gene (transgene) has been stably integrated into the plant genome. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event. Although more typically, compounds of the disclosure are used to control unwanted vegetation, contact of desired vegetation at the treated site with compounds of the disclosure may result in super-additive or synergistic effects with genetic traits on the desired vegetation, which includes traits incorporated through genetic modification. For example, resistance to phytophagous insect pests or plant diseases, tolerance to biotic / abiotic stresses, or storage stability may be higher than expected of the genetic traits in the desired vegetation. The compounds of this disclosure may also be mixed with one or more other biologically active compounds or agents including herbicides, herbicides, fungicides, insecticides, nematocides, bactericides, acaricides, growth regulators such as insect molting inhibitors, and stimulants. rooting agents, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds or entomopathogenic bacteria, viruses or fungi to form a multi-component pesticide that gives a broader uniform spectrum of agricultural protection. Mixtures of the compounds of the description with other herbicides can broaden the spectrum of activity against additional weed species, and suppress the proliferation of any of the resistant biotypes. Therefore, the present disclosure also pertains to a composition comprising a compound of Formula I (in a herbicidally effective amount) and at least one additional biologically active compound or agent (in a biologically active amount) and may further comprise at least one of a surfactant, a solid diluent or a liquid diluent. The other biologically active compounds or agents may be formulated into compositions comprising at least one of a solid or liquid surfactant, diluent. For mixtures of the present disclosure, one or more other biologically active compounds or agents may be formulated together with a compound of Formula I, to form a premix, or one or more other biologically active compounds or agents may be formulated separately from the compound of Formula I, and the formulations combined prior to application (eg, in a spray tank) or, alternatively, applied in succession. General references for crop protectants (i.e., herbicides, herbicide protectants, insecticides, fungicides, nematocides, acaricides, and biological agents) include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2001. For embodiments where one or more of these various mixing partners are used, the mixing partners are typically used in amounts similar to usual amounts when ncccnn / i ζηζ / Β / γ the mixing partners are used alone. More particularly in mixtures, active ingredients are often applied at an application rate between half and the full application rate specified on product labels for active ingredient-only use. These amounts are listed in references such as The Pesticide Manual and The BioPesticide Manual. The weight ratio of these various mixing partners (in total) to the compound of Formula I is typically between about 1:3000 and about 3000:1. Weight ratios between about 1:300 and about 300:1 (eg ratios between about 1:30 and about 30:1) stand out. One skilled in the art can readily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be apparent that including these additional components can expand the spectrum of weeds controlled beyond the spectrum controlled by the compound of Formula I alone. Of note is a composition comprising a compound of the invention (in a herbicidally effective amount), at least one additional active ingredient selected from the group consisting of other herbicides and herbicidal protectants (in an effective amount), and at least one component selected from the group consisting of surfactants, solid diluents and liquid diluents. Table A1 lists specific combinations of a Component (a) with Component (b) illustrative of the mixtures, compositions, and methods of the present invention. Compound No. 1 (this is "Com. No." stands for "Compound Number") in the Component (a) column is identified in Table AA. The second column of Table A1 lists the specific Component (b) compound (eg, "2,4-D" in the first line). The third, fourth, and fifth columns of Table A1 list ranges of weight ratios for rates at which the Component (a) compound is typically applied to a field-grown crop relative to Component (b) (i.e. (a ):(b)). Thus, for example, the first line of Table A1 specifically describes the combination of Component (a) (this is Compound No. 1 in Table AA) with 2,4-D typically applied in a weight ratio between 1: 192-6:1. The remaining lines of Table A1 should be interpreted in a similar way. ncccnn / i znz / B / v TABLE A1 Component (a) Ratio in Most Typical Weight Ratio Most Typical Weight Ratio (Com. No.) Component (b) Typical Weight 1 2,4-D 1:192-6:1 1:64-2:1 1:24-1:3 1 Acetochlor 1:768-2:1 1:256- 1:2 1:96-1:11 1 Acifluorfen 1:96-12:1 1:32-4:1 1:12- 1:2 1 Aclon ¡fen 1:857-2:1 1:285- 1:3 1:107-1:12 1 Alachlor 1:768-2:1 1:256- 1:2 1:96-1: 11 1 Ametrine 1:384-3:1 1:128-1:1 1:48-1:6 1 Amicarbazone 1:192-6:1 1:64-2:1 1:24 - 1:3 1 Amidosulfuron 1 :6-168:1 1:2-56:1 1:1 - 11:1 Relationship in Relationship in Weight Plus Weight Plus ncccnn / i 7Π7 / Β / Υ Component (a) Ratio in Typical Typical (Com. No.) Component (b) Weight Typical 1 Aminocyclopyrachlor 1:48-24:1 1:16-8:1 1:6-2:1 1 Aminopyralid 1:20-56 :1 1:6-19:1 1:2-4:1 1 Amitrol 1:768-2:1 1:256- 1:2 1:96-1:11 1 Anilofos 1:96-12:1 1: 32-4:1 1:12-1:2 1 Asulam 1:960-2:1 1:320- 1:3 1:120-1:14 1 Atrazine 1:192-6:1 1:64-2: 1 1:24-1:3 1 Azimsulfuron 1:6-168:1 1:2-56:1 1:1 - 11:1 1 Beflubutamid 1:342-4:1 1:114-2:1 1:42 -1:5 1 S-Beflubutamid 1:171 -4:0.5 1:57-2:0.5 1:21 - 1:2.5 1 Benfu resato 1:617-2:1 1:205- 1:2 1:77- 1:9 1 Bensulfuron-methyl 1:25-45:1 1:8-15:1 1:3-3:1 1 Bentazone 1:192-6:1 1:64-2:1 1:24-1: 3 1 Benzobicyclone 1:85-14:1 1:28-5:1 1:10-1:2 1 Benzofenap 1:257-5:1 1:85-2:1 1:32-1:4 1 Bicyclopyrone 1 :42-27:1 1:14-9:1 1:5-2:1 1 Bifenox 1:257-5:1 1:85-2:1 1:32 - 1:4 1 Bispiribac-sodium 1:10 -112:1 1:3-38:1 1:1 -7:1 1 Bixlozone 1:384-3:1 1:128-1:1 1:48 - 1:6 1 Bromacil 1:384-3:1 1:128-1:1 1:48 - 1:6 1 Bromobutide 1:384-3:1 1:128-1:1 1:48 - 1:6 1 Bromoxynil 1:96-12:1 1:32- 4:1 1:12 - 1:2 1 Butachlor 1:768-2:1 1:256- 1:2 1:96-1:11 1 Butafenacil 1:42-27:1 1:14-9:1 1 :5-2:1 1 Butylate 1:1542- 1:2 1:514-1:5 1:192-1:22 1 Carfenstrol 1:192-6:1 1:64-2:1 1:24-1 :3 1 Carfentrazone-ethyl 1:128-9:1 1:42-3:1 1:16-1:2 1 Chlorimuron-ethyl 1:8-135:1 1:2-45:1 1:1 -9 :1 1 Chlorotoluron 1:768-2:1 1:256- 1:2 1:96-1:11 1 Chlorsulfuron 1:6-168:1 1:2-56:1 1:1 - 11:1 1 Cincosulfuron 1:17-68:1 1:5-23:1 1:2-5:1 1 Cinidon-ethyl 1:384-3:1 1:128-1:1 1:48-1:6 1 Cinmethylin 1: 34-34:1 1:11 -12:1 1:4-3:1 1 Clacyphos 1:34-34:1 1:11 - 12:1 1:4-3:1 1 Clethodim 1:48-24: 1 1:16-8:1 1:6-2:1 Relationship in Relationship in Weight Plus Weight Plus ncccnn / i 7Π7 / Β / Υ Component (a) Ratio in Typical Typical (Com. No.) Component (b) Weight Typical 1 Clodinafop-propargyl 1:20-56:1 1:6-19:1 1:2-4:1 1 Clomazone 1:384 -3:1 1:128-1:1 1:48 - 1:6 1 Clomeprop 1:171 -7:1 1:57-3:1 1:21 - 1:3 1 Clopyralid 1:192-6:1 1:64-2:1 1:24-1:3 1 Chloransulam-methyl 1:12-96:1 1:4-32:1 1:1 -6:1 1 Cumiluron 1:384-3:1 1: 128-1:1 1:48-1:6 1 Cyanazine 1:384-3:1 1:128-1:1 1:48-1:6 1 Cyclopyrimorate 1:17-68:1 1:5-23: 1 1:2-5:1 1 Cyclosulfamuron 1:17-68:1 1:5-23:1 1:2-5:1 1 Cycloxidim 1:96-12:1 1:32-4:1 1:12 -1:2 1 Cihalofop 1:25-45:1 1:8-15:1 1:3-3:1 1 Daimuron 1:192-6:1 1:64-2:1 1:24-1:3 1 Desmedipham 1:322-4:1 1:107-2:1 1:40-1:5 1 Dicamba 1:192-6:1 1:64-2:1 1:24-1:3 1 Dichlobenyl 1: 1371 - 1:2 1:457- 1:4 1:171 - 1:20 1 Dichlorprop 1:925-2:1 1:308- 1:3 1:115-1:13 1 Diclofop-methyl 1:384- 3:1 1:128-1:1 1:48 - 1:6 1 Diclosulam 1:10-112:1 1:3-38:1 1:1 -7:1 1 Difenzoquat 1:288-4:1 1 :96-2:1 1:36 - 1:4 1 Diflufenican 1:857-2:1 1:285- 1:3 1:107-1:12 1 Diflufenzopyr 1:12-96:1 1:4-32 :1 1:1 -6:1 1 Dimethachlor 1:768-2:1 1:256- 1:2 1:96-1:11 1 Dimethamethrine 1:192-6:1 1:64-2:1 1: 24-1:3 1 Dimethenamide-P 1:384-3:1 1:128-1:1 1:48-1:6 1 Dithipyr 1:192-6:1 1:64-2:1 1:24- 1:3 1 Diuron 1:384-3:1 1:128-1:1 1:48-1:6 1 EPTC 1:768-2:1 1:256- 1:2 1:96-1:11 1 Esprocarb 1:1371 - 1:2 1:457- 1:4 1:171 - 1:20 1 Etalfluralin 1:384-3:1 1:128-1:1 1:48-1:6 1 Etamethsulfuron-methyl 1:17-68:1 1:5-23:1 1:2-5:1 1 Ethoxyfen 1:8-135:1 1:2-45:1 1:1 -9:1 1 Ethoxysulfuron 1:20- 56:1 1:6-19:1 1:2-4:1 1 Etobenzanid 1:257-5:1 1:85-2:1 1:32 - 1:4 1 Fenoxaprop-ethyl 1:120-10: 1 1:40-4:1 1:15-1:2 Component (a) Ratio in Most Typical Weight Ratio Most Typical Weight Ratio (Com. No.) Component (b) Typical Weight 1 Phenoxasulfone 1:85-14:1 1:28-5:1 1:10-1: 2 1 Phenquinotrione 1:17-68:1 1:5-23:1 1:2-5:1 1 Fentrazamide 1:17-68:1 1:5-23:1 1:2-5:1 1 Flazasulfuron 1 :17-68:1 1:5-23:1 1:2-5:1 1 Florasulam 1:2-420:1 1:1 -140:1 2:1 -27:1 1 Fluazifop-butyl 1:192 -6:1 1:64-2:1 1:24-1:3 1 Flucarbazone 1:8-135:1 1:2-45:1 1:1 -9:1 1 Flucetosulfuron 1:8-135:1 1:2-45:1 1:1 -9:1 1 Flufenacet 1:257-5:1 1:85-2:1 1:32 - 1:4 1 Flumetsulam 1:24-48:1 1:8- 16:1 1:3-3:1 1 Flumiclorac-pentyl 1:10-112:1 1:3-38:1 1:1 -7:1 1 Flumioxazin 1:25-45:1 1:8-15: 1 1:3-3:1 1 Fluometuron 1:384-3:1 1:128-1:1 1:48-1:6 1 Flupyrsulfuron-methyl 1:3-336:1 1:1 -112:1 2:1 -21:1 1 Fluridone 1:384-3:1 1:128-1:1 1:48 - 1:6 1 Fluroxypyr 1:96-12:1 1:32-4:1 1:12 - 1:2 1 Flurtamone 1:857-2:1 1:285- 1:3 1:107-1:12 1 Fluthiacet-methyl 1:48-42:1 1:16 - 14:1 1:3-3: 1 1 Fomesafen 1:96-12:1 1:32-4:1 1:12 - 1:2 1 Foramsulfuron 1:13-84:1 1:4-28:1 1:1 -6:1 1 Glufosinate 1 :288-4:1 1:96-2:1 1:36 - 1:4 1 Glyphosate 1:288-4:1 1:96-2:1 1:36 - 1:4 1 Halosulfuron-methyl 1: 17-68:1 1:5-23:1 1:2-5:1 1 Halauxifen 1:20-56:1 1:6-19:1 1:2-4:1 1 Halauxifen methyl 1:20-56 :1 1:6-19:1 1:2-4:1 1 Haloxyfop-methyl 1:34-34:1 1:11 -12:1 1:4-3:1 1 Hexazinone 1:192-6:1 1:64-2:1 1:24-1:3 1 Hydantocidin 1:1100-16:1 1:385-8:1 1:144-4:1 1 Imazamox 1:13-84:1 1:4- 28:1 1:1 -6:1 1 I mace pie 1:20-56:1 1:6-19:1 1:2-4:1 1 Imazapyr 1:85-14:1 1:28-5: 1 1:10-1:2 1 Imazaquin 1:34-34:1 1:11 -12:1 1:4-3:1 1 Imazetabenz-methyl 1:171 -7:1 1:57-3:1 1 :21 - 1:3 1 Imazethapyr 1:24-48:1 1:8-16:1 1:3-3:1 ncccnn / i ζπζ / β / υ Relationship in Relationship in Weight More Weight More Component (a) Ratio in Typical Typical (Com. No.) Component (b) Weight Typical 1 Imazosulfuron 1:27-42:1 1:9-14:1 1:3-3:1 1 Indanofan 1:342-4 :1 1:114-2:1 1:42 - 1:5 1 Indaziflam 1:25-45:1 1:8-15:1 1:3-3:1 1 mudsulfuron-methyl 1:3-336: 1 1:1 -112:1 2:1 -21:1 1 loxinil 1:192-6:1 1:64-2:1 1:24-1:3 1 Ipfencarbazone 1:85-14:1 1:28 -5:1 1:10-1:2 1 Isoproturon 1:384-3:1 1:128-1:1 1:48-1:6 1 Isoxabene 1:288-4:1 1:96-2:1 1:36-1:4 1 Isoxaflutole 1:60-20:1 1:20-7:1 1:7-2:1 1 Lactofen 1:42-27:1 1:14-9:1 1:5- 2:1 1 Lenacil 1:384-3:1 1:128-1:1 1:48-1:6 1 Linuron 1:384-3:1 1:128-1:1 1:48-1:6 1 MCPA 1:192-6:1 1:64-2:1 1:24-1:3 1 MCPB 1:288-4:1 1:96-2:1 1:36-1:4 1 Mecoprop 1:768 -2:1 1:256- 1:2 1:96-1:11 1 Mefenacet 1:384-3:1 1:128-1:1 1:48 - 1:6 1 Mefluidide 1:192-6:1 1:64-2:1 1:24 - 1:3 1 Mesosulfuron-methyl 1:5-224:1 1:1 -75:1 1:1 - 14:1 1 Mesotrione 1:42-27:1 1 :14-9:1 1:5-2:1 1 Metamifop 1:42-27:1 1:14-9:1 1:5-2:1 1 Metazachlor 1:384-3:1 1:128-1 :1 1:48 - 1:6 1 Metazosulfuron 1:25-45:1 1:8-15:1 1:3-3:1 1 Metabenzthiazuron 1:768-2:1 1:256- 1:2 1: 96-1:11 1 Metolachlor 1:768-2:1 1:256- 1:2 1:96-1:11 1 Metosulam 1:8-135:1 1:2-45:1 1:1 -9: 1 1 Metribuzin 1:192-6:1 1:64-2:1 1:24-1:3 1 Metsulfuron-methyl 1:2 - 560:1 1:1 -187:1 3:1 -35:1 1 Molinate 1:1028-2:1 1:342- 1:3 1:128-1:15 1 Napropamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Napropamide-M 1:192-6:1 1:64-2:1 1:24-1:3 1 Naptalam 1:192-6:1 1:64-2:1 1:24-1:3 1 Nicosulfuron 1:12- 96:1 1:4-32:1 1:1 -6:1 1 Norflurazon 1:1152-1:1 1:384- 1:3 1:144-1:16 1 Orbencarb 1:1371 - 1:2 1 :457 - 1:4 1:171 - 1:20 Relationship in Relationship in Weight More Weight More Component (a) Ratio in Typical Typical (Com. No.) Component (b) Weight Typical 1 Orthosulfamuron 1:20-56:1 1:6-19:1 1:2-4:1 1 Oryzalin 1:514-3 :1 1:171 - 1:2 1:64 - 1:8 1 Oxadiargyl 1:384-3:1 1:128-1:1 1:48 - 1:6 1 Oxadiazon 1:548-3:1 1: 182-1:2 1:68-1:8 1 Oxasulfuron 1:27-42:1 1:9-14:1 1:3-3:1 1 Oxaziclomefone 1:42-27:1 1:14-9: 1 1:5-2:1 1 Oxyfluorfen 1:384-3:1 1:128-1:1 1:48-1:6 1 Paraquat 1:192-6:1 1:64-2:1 1:24 -1:3 1 Pendimetalin 1:384-3:1 1:128-1:1 1:48 - 1:6 1 Penoxsulam 1:10-112:1 1:3-38:1 1:1 -7:1 1 Pentoxamid 1:384-3:1 1:128-1:1 1:48-1:6 1 Pentoxazone 1:102-12:1 1:34-4:1 1:12-1:2 1 Fenmedipham 1: 102-12:1 1:34-4:1 1:12-1:2 1 Picloram 1:96-12:1 1:32-4:1 1:12-1:2 1 Picolinafen 1:34-34: 1 1:11 - 12:1 1:4-3:1 1 Pinoxaden 1:25-45:1 1:8-15:1 1:3-3:1 1 Pretilachlor 1:192-6:1 1:64 -2:1 1:24 - 1:3 1 Primisulfuron-methyl 1:8-135:1 1:2-45:1 1:1 -9:1 1 Prodiamine 1:384-3:1 1:128-1 :1 1:48 - 1:6 1 Prophoxydim 1:42-27:1 1:14-9:1 1:5-2:1 1 Promethrin 1:384-3:1 1:128-1:1 1: 48 - 1:6 1 Propachlor 1:1152-1:1 1:384- 1:3 1:144-1:16 1 Propanil 1:384-3:1 1:128-1:1 1:48-1: 6 1 Propaquizafop 1:48-24:1 1:16-8:1 1:6-2:1 1 Propoxycarbazone 1:17-68:1 1:5-23:1 1:2-5:1 1 Propyrisulfuron 1 :17-68:1 1:5-23:1 1:2-5:1 1 Propyzamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Prosulfocarb 1:1200-1 :2 1:400- 1:4 1:150-1:17 1 Prosulfuron 1:6-168:1 1:2-56:1 1:1 - 11:1 1 Pyraclonil 1:42-27:1 1: 14-9:1 1:5-2:1 1 Pyraflufen-ethyl 1:5-224:1 1:1 -75:1 1:1 - 14:1 1 Pyrasulfotol 1:13-84:1 1:4- 28:1 1:1 -6:1 1 Pyrazolinate 1:857-2:1 1:285- 1:3 1:107-1:12 1 Pyrazosulfuron-ethyl 1:10-112:1 1:3-38 :1 1:1 -7:1 Relationship in Relationship in Weight More Weight More Component (a) Ratio in Typical Typical (Com. No.) Component (b) Weight Typical 1 Pyrazoxifene 1:5-224:1 1:1 -75:1 1:1 - 14:1 1 Pyribenzoxim 1:10-112 :1 1:3-38:1 1:1 -7:1 1 Pyributicarb 1:384-3:1 1:128-1:1 1:48 - 1:6 1 Pyridate 1:288-4:1 1: 96-2:1 1:36-1:4 1 Piriftalid 1:10-112:1 1:3-38:1 1:1 -7:1 1 Piriminobac-methyl 1:20-56:1 1:6- 19:1 1:2-4:1 1 Pirimisulfan 1:17-68:1 1:5-23:1 1:2-5:1 1 Pyritiobac 1:24-48:1 1:8-16:1 1 :3-3:1 1 Pyroxasulfone 1:85-14:1 1:28-5:1 1:10-1:2 1 Pyroxsulam 1:5-224:1 1:1 -75:1 1:1 - 14 :1 1 Quinclorac 1:192-6:1 1:64-2:1 1:24-1:3 1 Quizalofop-ethyl 1:42-27:1 1:14-9:1 1:5-2:1 1 Rimsulfuron 1:13-84:1 1:4-28:1 1:1 -6:1 1 Saflufenacil 1:25-45:1 1:8-15:1 1:3-3:1 1 Sethoxydim 1: 96-12:1 1:32-4:1 1:12 - 1:2 1 Simazine 1:384-3:1 1:128-1:1 1:48 - 1:6 1 Sulcotrione 1:120-10: 1 1:40-4:1 1:15-1:2 1 Sulfentrazone 1:147-8:1 1:49-3:1 1:18-1:3 1 Sulfometuron-methyl 1:34-34:1 1 :11 - 12:1 1:4-3:1 1 Their messes ulfuron 1:8-135:1 1:2-45:1 1:1 -9:1 1 Tebuthiuron 1:384-3:1 1 :128-1:1 1:48 - 1:6 1 Tefuryltrione 1:42-27:1 1:14-9:1 1:5-2:1 1 Tembotrione 1:31 -37:1 1:10-13 :1 1:3-3:1 1 Tepraloxydim 1:25-45:1 1:8-15:1 1:3-3:1 1 Terbacil 1:288-4:1 1:96-2:1 1: 36-1:4 1 Terbutylazine 1:857-2:1 1:285- 1:3 1:107-1:12 1 Terbutrin 1:192-6:1 1:64-2:1 1:24-1: 3 1 Tenilchlor 1:85-14:1 1:28-5:1 1:10-1:2 1 Thiazopyr 1:384-3:1 1:128-1:1 1:48-1:6 1 Thiencarbazone 1 :3-336:1 1:1 -112:1 2:1 -21:1 1 Thifensulfuron-methyl 1:5-224:1 1:1 -75:1 1:1 - 14:1 1 Thiafenacil 1: 17-68:1 1:5-23:1 1:2-5:1 1 Thiobencarb 1:768-2:1 1:256- 1:2 1:96-1:11 1 Tolpyralate 1:31 -37: 1 1:10-13:1 1:3-3:1 Relationship in Relationship in Weight Plus Weight Plus Component (a) Ratio in Typical Typical (Com. No.) Component (b) Weight Typical 1 Topramzone 1:6-168:1 1:2-56:1 1:1 - 11:1 1 Tralkoxydim 1 :68-17:1 1:22-6:1 1:8-2:1 1 Triafamone 1:2-420:1 1:1 - 140:1 2:1 -27:1 1 Trialllate 1:768-2 :1 1:256- 1:2 1:96-1:11 1 Triasulfuron 1:5-224:1 1:1 -75:1 1:1 - 14:1 1 Triaziflam 1:171-7:1 1: 57-3:1 1:21 -1:3 1 Tribenuron-methyl 1:3-336:1 1:1 -112:1 2:1 -21:1 1 Triclopyr 1:192-6:1 1:64- 2:1 1:24-1:3 1 Trifloxysulfuron 1:2-420:1 1:1 - 140:1 2:1 -27:1 1 Trifludimoxazin 1:25-45:1 1:8-15:1 1 :3-3:1 1 Trifluralin 1:288-4:1 1:96-2:1 1:36-1:4 1 Triflusulfuron-methyl 1:17-68:1 1:5-23:1 1: 2-5:1 1 Tritosulfuron 1:13-84:1 1:4-28:1 1:1 -6:1 ncccnn / i ζπζ / β / υ Table A2 is constructed in the same way as Table A1 above except that the entries under the “Component (a)” column heading are replaced with the respective Component (a) Column Entry shown below. Compound No. 2 in the Component (a) column is identified in Table AA. Thus, for example, in Table A2 the entries under the column heading "Component (a)" all refer to "Compound No. 2" (this is Compound No. 2 identified in Table AA), and the first line by under the column headings in Table A2 specifically describe a mixture of Compound No. 2 with 2,4D. Table Number Component Column Entries (a) A2 Composite No. 4 A3 Composite No. 5 A4 Composite No. 9 A5 Composite No. 12 A6 Composite No. 13 A7 Composite No. 18 A8 Composite No. 20 A9 Composite No. 21 A10 Compound No. 22 A11 Compound No. 23 A11 Compound No. 29 A12 Compound No. 31 64 Table Number Component Column Entries (a) A13 Compound No. 32 A14 Compound No. 33 A15 Compound No. 35 A16 Compound No. 36 A17 Compound No. 40 A18 Compound No. 65 A19 Compound No. 66 A20 Compound No 77 ncccnn / i 7Π7 / Β / Υ In certain cases, combinations of a compound of this disclosure with other biologically active compounds (particularly herbicides) or agents (ie active ingredients) may result in a greater than additive (ie synergistic) effect on weeds and / or a lesser effect. What an additive (this is savior) on crops or other desirable plants. Reducing the amount of active ingredients released into the environment while ensuring effective pest control is always desirable. The ability to use larger amounts of active ingredients to provide more effective weed control without excessive crop damage is also desirable. When synergism of herbicidal active ingredients occurs on weeds at application rates that give agronomically satisfactory levels of weed control, such combinations may be advantageous in reducing crop production cost and environmental burden. When the herbicidal active ingredient savior is present in crops, such combinations may be advantageous for increasing crop protection by reducing weed competition. Of note is a combination of a compound of the description with at least one other herbicidal active ingredient. Of particular interest is such a combination where the other herbicidal active ingredient has a different site of action from the compound of the description. In certain cases, a combination with at least one other herbicidal active ingredient that has a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present disclosure may further comprise (in a herbicidally effective amount) at least one additional herbicidal active ingredient having a similar spectrum of control but a different site of action. Compounds of this description can also be used in combination with herbicidal protectants such as alidochlor, benoxacor, cloquintocet-mexyl, cumiluron, ciometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, phenchlorazole-ethyl, fenchlorim, flurazole, fluxofenim, furilazole , isoxadiphen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone naphthalic anhydride (1,8naphthalic anhydride), oxabetrinyl, / V-(aminocarbonyl)-2-methylbenzenesulfonamide, / V-(aminocarbonyl)-2fluorobenzenesulfonamide, 1-bromo-4-[ (chloromethyl)sulfonyl]benzene (BCS), 4-(dichloroacetyl)-1-oxa-4azospiro[4.5]decane (MON 4660), 2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), Ethyl 1,6-dihydro-1-(2methox¡phenyl)-6-oxo-2-phenyl-5-pyr¡m¡ncarboxylate, 2-hidrox¡- / V, / V-d ¡methyl-6-(trifluoromethyl)pyridine-365 carboxamide, 1 -(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl -5-pyrimidinecarboxylate, 2,2-dichloro-1-(2,2,5trimethyl-3-oxazoldinyl)-ethanone and 2-methoxy- / V-[[4-[[ (methylam¡no)carbon¡l]am¡no]fen¡l]sulfonil]-benzamida to increase safety to certain crops. Antidote-effective amounts of the herbicidal protectants can be applied at the same time as the compounds of this disclosure, or applied as seed treatments. Therefore one aspect of the present description relates to a mixture of herbicides comprising a compound of this description and an antidote-effective amount of a herbicidal protectant. Seed treatment is particularly useful for selective weed control, because it physically restricts the antidote to crop plants. Therefore a particularly useful embodiment of the present disclosure is a method of selectively controlling the growth of unwanted vegetation in a crop comprising contacting the harvest site with a herbicidally effective amount of a compound of this disclosure wherein the Seed from which the crop is grown is treated with a protectant antidote level effective amount. Antidote-effective amounts of protectants can be readily determined by one skilled in the art through simple experimentation. Compounds of the disclosure may also be mixed with: (1) polynucleotides including but not limited to DNA, RNA, and / or chemically modified nucleotides that influence the amount of a particular target through down-regulation, interference , suppression or silencing of the genetically derived transcript that produces a herbicidal effect; or (2) polynucleotides including but not limited to DNA, RNA, and / or chemically modified nucleotides that influence the amount of a particular target through downregulation, interference, suppression, or silencing of the genetically derived transcript that produces a saving effect. The following Tests A through M demonstrate the control efficacy of representative compounds of this disclosure against representative weeds, but the weed control provided by these compounds is not limited to these species. See Table 1 of the index for compound descriptions. Mass spectra are reported with an accuracy estimated to within ±0.5 Da as the molecular weight of the highest isotopically abundant parent ion (M+1) formed by the addition of H+ (molecular weight of 1) to the observed molecule using chemical ionization. at atmospheric pressure (AP+). ncccnn / i 7Π7 / Β / Υ TABLE 1 INDEX Yo Com. No. R1 R2 R3 R5 R6 Physical properties 21 CH3 Cl OH F H M.P.=192-195°C 22 ch3 Cl OH Cl H M.P. = 232-235°C 20 ch3 Cl OH ch3 H See above* 65 ch3 Cl OH H Cl ncccnn / i ζπζ / β / υιλι * See synthesis EXAMPLE 3 for physical property data. “1H NMR (DMSO-de) δ 11.22 (brs, 1H), 8.18-8.20 (m, 1H), 7.72 (s, 1H), 7.60-7.66 (m, 1H), 7.50-7.57 (m, 2H), 3.64 (s, 3H), 2.20 (s, 3H). TEST A Seeds of selected plant species of barn (Echinochloa crus-gallí), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosia elatior), ryegrass, Italian (Lolium multiflorum), foxtail, giant (Setaria faberíí), fox, green (Setaria viridís) and red pigweed (Amaranthus retroflexus) were planted in a mixture of loam and sand and treated pre-emergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture which included a surfactant. At the same time, selected plants of these weed species and also wheat (Triticum aestivum), maize (Zea mays), blackgrass (Alopecuros myosuroides) and gallium (weed-catch curdle, Galio aparine) were planted in pots containing the same mixture of loam soil and sand and were treated with post-emergence applications of test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were at the one- to two-leaf stage for post-emergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 10 days, after which time all treated plants were compared to untreated controls and visually assessed for lesions. Plant response ratings, summarized in Table A, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table A Composites Table A Composites 125 g ai / ha 20 21 22 65 31 g ai / ha 20 21 22 65 Post-emergence Post-emergence Barn 100 90 100 100 Barn 80 80 100 100 Black grass 60 70 100 100 Black grass 0 50 70 90 Corn 30 20 10 50 Corn 30 10 0 30 Foxtail, Giant 100 - -100 Foxtail, Giant 80 - -100 Foxtail, Green - 100 100 - Foxtail, Green - 90 100 - Gallium 100 100 100 100 Gallium 90 100 100 100 Kochia 90 90 100 100 Kochia 70 80 60 80 Red Pigweed 100 100 100 100 Red Pigweed 90 100 100 100 Ambrosia 90 100 100 100 Ryegrass, Italian 100 100 100 100 Wheat 30 80 100 90 Ambrosia 90 100 100 100 Ryegrass, Italian 90 90 100 100 Wheat 20 50 100 80 ncccnn / i ζπζ / β / υιλι Table A Composites 125 g ai / ha 20 21 22 65 Prior to the emergency Barn 100 100 100 100 Foxtail, Giant 100 - - 100 Fox Tail, Green - 100 100 Kochia 90 100 90 80 Red pigweed 100 100 100 100 Ambrosia 90 100 100 100 Table A Composites g ai / ha 20 21 22 65 Prior to the emergency Barn 70 90 100 100 Foxtail, Giant 80 - - 100 Foxtail, Green - 70 90 Ryegrass, Italian 100 100 100 100 Kochia 30 50 10 0 Red pigweed 100 100 100 100 Ambrosia 20 100 100 100 Ryegrass, Italian 90 80 90 100 TEST B Plant species in the flooded rice trial selected from rice (Oryza sativa), nut shell, umbrella (small-flowered umbrella shell, Cyperus difformis), duck salad (Heteranthera limosa) and granary (Echinochloa crus-galli) were grown until 2-leaf stage for testing. At the time of treatment, the test pots were flooded to 3 cm above the soil surface, treated by applying test compounds directly to the paddy water, and then kept in that depth of water for the duration of the test. the proof. Treated plants and controls were kept in a greenhouse for 13 to 15 days, after which time all species were compared to controls and evaluated visually. Plant response ratings, summarized in Table B, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table B Flooding compounds 250 g ai / ha 20 21 22 65 Barn 25 80 40 40 Duck salad 100 90 90 80 Rice 15 35 60 20 Coquillo, Umbrella 90 90 85 90 TEST C Seeds of selected plant species of blackgrass (Alopecuros myosuroides), ryegrass, Italian (Lolium multiflorum), winter wheat (winter wheat, Triticum aestivum), gallium (catch weed curdle, Galio aparine), grain (Zea mays), crabgrass, large (Digitada sanguinalís), foxtail, giant (Setaria faberíi), Johnson grass (Sorgo halepense), white quinoa (Chenopodium album), bluebells (Ipomoea coccinea), chives, yellow (Cyperus esculentus), red pigweed (Amaranthus retroflexus), ragweed (ragweed, Ambrosia elatior), soybean (Glycine max), barn (Echinochloa crus-gallí), rapeseed (Brassica napus), hemp (common hemp, Amaranthus rudis), red pigweed, palm ( Amaranthus palmera!), kochia (Kochia scoparia), oats, wild (Avena fatua), Suriname grass (Brachíaria decumbens), wind grass (Apera spica-venti), poinsettia, wild (Euphorbia heterophylla) and velvet mallow ( Abutilon theophrasti) were planted in a silt loam and treated prior to emergence with test chemicals formulated in a non-phytotoxic solvent mixture that included a surfactant. At the same time, selected plants of these crops and weed species and also chickweed (common chickweed, Stellaria media), buckwheat, wild (Polygonum convolvulus), mustard, wild (Sinapis arvensis), field poppy (Papaver rhoeas), violet field geranium (Viola arvensis), nightshade (eastern black nightshade, Solanum ptycanthum), speedwell (bird's-eye speedwell, Veronica persica), horsewort (Conyza canadensis), cutleaf geranium (Geranium dissectum), and Canada thistle (Cirsium arvense) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat moss, vermiculite, wetting agent, and starter nutrients. and treated with post-emergence applications of similarly formulated test chemicals. Plants ranged in height from 2 to 18 cm (1 to 4 leaf stage) for postemergence treatments. Treated and control plants were kept in a greenhouse for 13 to 21 d, after which time all species were compared to controls and evaluated visually. Facility response ratings, summarized in Table C-1 (post-emergency) and C-2 (pre-emergency), are based on a scale of 0 to 100 where 0 has no effect and 100 is control. complete. A dash (-) response means no test result. Plant species in the flooded rice test consisted of rice (transplanted and seeded with water, Oryza sativa), nutsedge, umbrella (small-flowered umbrella nuts, Cyperus difformis), duck salad (Heteranthera limosa), Cattail, Japanese (Scirpus juncoides) and barn (Echinochloa crus-gallí) grown to the 2-leaf stage for the test. At the time of treatment, test pots were flooded to 3 cm above the soil surface, treated by applying test compounds directly to the paddy water, and then kept in that depth of water for the duration of the treatment. proof. Treated and control plants were kept in a greenhouse for 13 to 15 d, after which time all species were compared to controls and evaluated visually. Plant response ratings, summarized in Table C, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Table C Compounds Table C Compounds 125gia / ha 20 21 22 65 62 g ai / ha 20 21 22 65 Post-emergence Post-emergence ncccnn / i 7Π7 / Β / Υ Barn 85 90 95 100 Barn 75 90 95 100 Black Grass 45 70 100 95 Black Grass 40 65 90 90 Buckwheat, Wild - -100 100 Buckwheat, Wild - -100 100 Canada Thistle - - 100 90 Canada Thistle - - 100 98 Chickweed 98 - 100 98 Chickweed 95 - 100 95 Corn 20 18 25 75 Corn 5 15 35 65 Crabgrass, Large 80 70 60 70 Crabgrass, Large 70 40 15 40 Cutleaf Geranium - - 85 95 Cutleaf Geranium - - 85 95 Field Poppy - 98 100 100 Field Poppy - 75 75 98 Field Violet - - 80 85 Field Violet - - 75 85 Foxtail, Giant 95 93 98 98 Foxtail, Giant 85 90 95 98 Galio 95 78 98 98 Gallium 95 98 95 95 Horsegrass - 90 - - Horsegrass - 90 - - Johnson Grass 35 - 60 85 Johnson Grass 30 - 50 75 Kochia 98 28 70 75 Kochia 90 28 65 65 White Quinoa 95 - 85100 White Quinoa 95 - 100 100 Bluebells 100 - 100 100 Bluebells 100 - 100 100 Mustard, Wild - -100 100 Mustard, Wild - -100 100 Nightshade - - -100 Nightshade - - -100 Chives, Yellow 98 - 85 95 Chives, Yellow 95 - 90 65 Oats, Wild 90 100 100 100 Oats, Wild 70 99 100 100 Rapeseed 0 -100 100 Rapeseed 0 - 95 100 Red Pigweed 98 - - - Red Pigweed 95 - - - Red Pigweed, Palm Tree - 95 75 95 Red Pigweed , Palm - 30 70 60 Poinsettia, Wild - - 35 100 Poinsettia, Wild - - 40 80 Ragweed 98 98 100 98 Ragweed 95 98 100 98 Ryegrass, Italian 95 - 100 95 Ryegrass, Italian 95 - 95 95 Soybean 20 23 25 85 Soybean 10 20 20 80 Persian Speedwell - - 90 90 Persian Speedwell - - 75 75 Suriname Grass - - 95 95 Suriname Grass - - 95 95 Velvet Mauve 90 - 85100 Velvet Mauve 85 - 80100 Hemp 95 90 90 95 C hemp 95 98 85 95 Wheat 0 80 95 95 Wheat 0 78 90 95 Wind grass - - 100 95 Wind grass - - 100 95 Table C Composites Table C Composites 31 g ai / ha 20 21 22 65 16 g ai / ha 20 21 22 65 Post-emergency Post-emergency ncccnn / i 7Π7 / β / υ Barn 75 85 90 85 Black Grass 30 60 85 90 Buckwheat, Wild - -100 100 Canada Thistle - - 80 90 Chickweed 95 - 98 95 Corn 5 0 20 40 Crabgrass, Large 40 70 25 40 Cut Leaf Geranium - - 80 90 Field Poppy - 70 75 98 Field Violet - - 70 80 Foxtail, Giant 85 85 90 95 Gallium 95 95 85 90 Horseweed - 85 - - Johnson Grass 10 - 40 40 Kochia 85 18 35 55 White Quinoa 90 - 85 98 Bluebells 100 - 100 100 Mustard, Wild - - 75 100 Nightshade - - - 100 Chives, Yellow 90 - 35 75 Oats, Wild 55 98 100 100 Rapeseed 0 - 90 100 Red Pigweed 95 - - - Red Pigweed, Palm - 30 70 55 Poinsettia, Wild - - 25 95 Ragweed 90 95 95 100 Ryegrass, Italian 85 - 85 95 Soybean 10 13 10 75 Persian Speedwell - - 60 65 Suriname Grass - - 85 90 Velvet Mauve 75 - 60 85 Hemp 70 85 85 90 Wheat 0 65 90 95 Wind grass - - 85 90 Barn 55 60 85 80 Black grass 20 35 70 55 Buckwheat, Wild - - 95 100 Canada Thistle - - 80 80 Chickweed 95 - 100 98 Corn 0 0 0 30 Crabgrass, Large 40 40 10 30 Cutleaf Geranium - - 70 85 Field Poppy - 60 75 80 Field Violet - - 60 70 Foxtail, Giant 70 70 85 95 Gallium 95 90 85 90 Horseweed - 80 - - Johnson Grass 5 - 20 20 Kochia 80 13 25 40 White Quinoa 75 - 80 90 Bluebells 100 - 85 98 Mustard, Wild - - 75 98 Nightshade - - - 90 Chives, Yellow 90 - 10 50 Oats, Wild 35 95 98 98 Rapeseed 0 - 85 95 Red pigweed 90 - - Red Pigweed, Palm Tree - 30 50 35 Poinsettia, Wild - 25 70 Ragweed 85 90 90 98 Ryegrass, Italian 65 - 70 85 Soybean 0 10 5 65 Persian Speedwell - - 50 55 Suriname Grass - - 80 90 Velvet Mauve 7C I - 55 40 Hemp 75 80 75 80 Wheat wind grass 45 85 90 - - 85 90 Table C Compounds 125 g ai / ha 20 21 22 65 Prior to the emergency Table C Compounds g ai / ha 20 21 22 65 Prior to the emergency ncccnn / i 7Π7 / Β / Υ Barn 100 95 100 75 Black grass 90 85 85 85 Corn 35 20 30 15 Crabgrass, Large 100 65 85 65 Foxtail, Giant 100 100 100 100 Gallium 100 95 95 100 Johnson Grass 65 65 7020 Kochia - 90 95 90 White quinoa 100 98 100 100 Bells 95 95 8595 Chives, Yellow 98 95 9595 Oats, Wild - 85 95 60 Rapeseed 0 100 100 100 Red pigweed 100 - - Red pigweed, Palm tree - 90 100 100 Barn 95 85 85 60 Black grass 85 85 30 55 Corn 5 5 5 5 Crabgrass, Large 95 30 75 60 Foxtail, Giant 100 98 100 95 Gallium 100 95 70 98 Johnson Grass 30 50 50 5 Kochia - 70 80 85 white quinoa 100 85 90 90 Bells 95 80 - 98 Chives, Yellow 95 85 75 75 Oats, Wild -85 45 40 Rapeseed 0 98 100 98 ncccnn / i znz / B / v Poinsettia, Wild - 25 35 100 Ragweed 100 95 100 100 Ryegrass, Italian 100 100 90 95 Soybean 60 0 30 30 Suriname Grass - 100 100 100 Velvet Mauve 100 95 80 100 Hemp 100 98 95 95 Wheat 70 90 100 90 Wind Grass - 98 100 100 Red pigweed 100 - - Red pigweed, Palm tree - 70 75 100 Poinsettia, Wild - 10 10 70 Ambrosia 100 98 9098 Ryegrass, Italian 100 98 9895 Soy 20 0 05 Suriname Lawn - 100 95 70 Velvet mauve 100 75 9075 Hemp 100 95 9585 Wheat 60 90 95 80 Wind Grass - 85 85 95 Table C Compounds Table C Compounds 31 g ai / ha 20 21 22 65 16 g ai / ha 20 21 22 65 Pre-emergence Pre-emergence Barn 85 75 65 20 Barn 70 25 5 10 Black grass 85 50 25 5 Black grass 20 35 5 10 Corn 0 0 10 0 Corn 0 0 5 0 Crabgrass, Large 60 25 25 0 Crabgrass, Large 60 0 5 0 Foxtail, Giant 100 85 80 75 Foxtail, Giant 98 10 0 35 Gallium 100 95 50 85 Gallium 98 90 20 0 Johnson Grass 40 10 30 5 Johnson Grass 35 5 5 0 Kochia - 20 5 70 Kochia - 5 0 20 White Quinoa 75 70 75 80 White Quinoa 80 75 70 20 Campanillas 85 40 35 90 Campan islands 70 5 25 55 Chives, Yellow 95 60 50 75 Oats, Wild - 70 30 35 Rapeseed 0 85 0 5 Red Pigweed 10C ) - - - Red Pigweed, Palm 55 65 70 Poinsettia, Wild 5 5 35 Ambrosia 100 100 60 95 Ryegrass, Italian 100 98 25 70 Soybean 0 0 5 0 Suriname Grass - 100 90 55 Velvet Mauve 100 75 60 60 Hemp 100 85 85 75 Wheat 60 90 85 ( 30 Wind Grass - 75 80 80 Table C 250 g ai / ha Flooding compounds 21 65 Barn 20 65 100 Duck salad 85 85100 Rice, Transplanted 0 1570 Rice, Planted with water 0 - Coquillo, Umbrella 70 0100 Table C Compounds g ai / ha 20 21 65 Flood Barn 0 10 Cattail,Japanese - - 75 Duck salad 30 30 100 Rice, Transplanted 0 0 0 Rice, Sown with water 0 - Coquillo, Umbrella 0 0 100 Chives, Yellow 40 30 25 10 Oats, Wild - 45 0 30 Rapeseed 0 0 0 5 Red Pigweed 100 - - - Red Pigweed, Palm Tree - 20 40 50 Poinsettia, Wild - 0 5 25 Ambrosia 65 45 60 65 Ryegrass, Italian 98 50 5 40 Soybean 0 0 0 0 Suriname Grass - 8C I 7' 5 15 Velvet Mauve 85 40 10 40 Hemp 65 80 70 80 Wheat 0 5 6 0 3 Ό Wind Grass - 50 0 50 Table C Composites 125 g ai / ha 20 21 65 Flood Barn 0 30 30 Cattail, Japanese - - 90 Duck Salad 70 80 100 Rice, Transplanted 0 0 20 Rice, Seed with water 0-10 Coquillo, Umbrella 50 0 100 Table C Composites 31 g ai / ha 20 21 65 Flooding Barn 0 0 0 Duck salad 0 0 95 Rice, Transplanted 0 0 0 Rice, Planted with water 0 - Coquillo, Umbrella 0 0 95 TEST D Seeds of selected plant species of blackgrass (Alopecurus myosuroides), gallium (weed catch curdle, Galio aparíne), kochia (Kochia scoparía), rapeseed (Brassica napus), ncccnn / i znz / B / v barley, spring ( Hordeum vulgare), wheat, spring (Triticum aestivum), oats, wild (Avena fatua), barley, winter (Hordeum vulgare) and wheat, winter (Triticum aestivum) were planted in a silt loam and treated in advance. to the emergency with test chemicals formulated in a non-phytotoxic solvent mixture that included a surfactant. At the same time, selected plants of these crops and weed species and also bluegrass (annual bluegrass, Poa annua), canarygrass (small-seeded canarygrass, Phalaris minor), chickweed (common chickweed, Stellaria media) , brome, downy (downy brome, Bromus tectorum), field poppy (Papaver rhoeas), field violet (Viola arvensis), foxtail, green (Setaria viridis), dead nettle (dead nettle henbit, Lamium amplexicaule), ryegrass , Italiana (Lolium multiflorum), White quinoa (Chenopodium album), Red pigweed (Amaranthus retroflexus), Chamomile (Odorless chamomile, Matricaria inodora), Russian thistle (Salsola kali), Persian speedwell (Bird's-eye speedwell, Persian speedwell ), buckwheat, wild (Polygonum convolvulus), mustard, wild (Sinapis arvensis), radish, wild (Raphanus raphanistrum), windweed (Apera spica-venti), geranium, cutleaf (Geranium dissectum), and Canada thistle (Cirsium arvense) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat moss, vermiculite, wetting agent and starter nutrients and treated with subsequent applications. to the emergence of test chemicals formulated in the same way. Plants ranged in height from 2 to 18 cm (1 to 4 leaf stage). Treated and control plants were maintained in a controlled growth environment for 14 to 21 d after which time all species were compared to controls and evaluated visually. Plant response ratings, summarized in Table D, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. ncccnn / i 7Π7 / Β / Υ Table D Composites Table D Composites 125 g ai / ha 20 65 62 g ai / ha 20 22 65 Post-emergence Post-emergence Barley, spring 20 93 Barley, spring 10 85 88 Barley, winter 15 90 Barley, spring Winter 15 73 83 Black Grass 60 95 Black Grass 50 82 93 Blue Grass 10 - Blue Grass 5 - - Brome, Downy 25 - Brome, Downy 10 - - Buckwheat, Wild 100 - Buckwheat, Wild 99 - - Canada Thistle 95 - Thistle Canada 95 - - Canary grass 35 - Canary grass 20 - - Chamomile 100 100 Chamomile 100 -100 Chickweed 100 - Chickweed 100 - - Dead nettle 95 - Dead nettle 85 - - Field poppy 100 - Field poppy 100 - - Field Violet 95 - Field Violet 95 - - Foxtail, Green 98 - Foxtail, Green 95 - - Gallium 99 98 Gallium 90 96 97 Geranium, Cut Leaf 85 - Geranium, Cut Leaf 80 - - Kochia 80 90 Kochia 70 58 75 White quinoa 98 - White quinoa 90 - - Mustard, Wild 60 - Mustard, Wild 30 - - Oats, Wild 90 99 Oats, Wild l 30 98 96 Rapeseed 25 100 Rapeseed 20 90 90 Red Pigweed 100 - Red Pigweed 100 - - Radish, Wild 25 - Radish, Wild 15 - - Russian Thistle 85 - Russian Thistle i 80 - - Ryegrass, Italian 90 - Ryegrass, Italian I 30 - - Speedwell 85 - Speedwell 80 - - Wheat, spring 55 93 Wheat , spring 35 96 93 Wheat, winter 30 92 Wheat, winter 20 95 90 Wind grass 75 - Wind grass 50 - - Table D Composites Table D Composites 31 g ai / ha 20 22 65 16 g ai / ha 20 65 Post-emergence Post-emergence Barley, spring 5 67 78 Barley, spring 0 57 Barley, winter 5 47 72 Barley, winter 0 60 Black grass 25 75 90 Black grass 15 83 Blue grass 5 - - Grass blue 0 - Bromine, Downy 5 - - Bromine, Downy 0 - Buckwheat, Wild 98 - - Buckwheat, Wild 100 - Canada Thistle 85 - - Canada Thistle 75 - Canary Grass 15 - - Canary Grass 10 - Chamomile 98 - 100 Chamomile 95 99 Chickweed 99 - - Chickweed 99 - Dead nettle 80 - - Dead nettle 35 - Field poppy 85 - - Field poppy 80 - Field violet 80 - - Field violet 80 - Foxtail, Green 90 - - Foxtail, Green 85 - Gallium 90 92 97 Gallium 80 85 Geranium, Cut Leaf 75 - - Geranium, Cut Leaf 65 - Kochia 70 37 50 Kochia 70 35 ncccnn / i 7Π7 / ε / υ White quinoa 95 - - White quinoa 90 - Mustard, Wild 25 - - Mustard, Wild 20 - Oats, Wild 65 93 92 Oats, Wild 25 92 Rapeseed 15 73 87 Rapeseed 15 85 Red pigweed 98 - - Red pigweed 98 - Radish, Wild 0 - - Radish, Wild 0 - Russian Thistle 75 - - Russian Thistle 80 - Ryegrass, Italian 75 - - Ryegrass, Italian 65 - Speedwell 60 - - Speedwell 50 - Wheat, spring 25 90 93 Wheat, spring 15 90 Wheat, winter 15 85 90 Wheat, winter 10 85 Windgrass 25 - - Windgrass 15 - ncccnn / i 7Π7 / Β / Υ Table D 125 g ai / ha Compounds 20 65 Pre-emergence Barley, spring 10 73 Barley, winter 0 23 Black grass 58 90 Gallium 100 100 Kochia 80 93 Oats, Wild 83 97 Rapeseed 0 100 Wheat, spring 62 100 Wheat , winter 17 93 Table D Compounds 62 g ai / ha 20 65 Pre-emergence Barley, spring 2 5 Barley, winter 0 7 Black grass 20 63 Gallium 97 98 Kochia 35 72 Oats, Wild 73 83 Rapeseed 0 85 Wheat, spring 28 90 Wheat, winter 5 80 Table D Compounds g ai / ha20 65 Prior to the emergency Barley, spring0 3 Barley, winter0 3 black grass8 23 gallium85 82 Kochia25 22 Oats, Wild33 80 Rapeseed0 18 Wheat, spring12 78 Wheat, winter0 67 Table D Compounds 16 g ai / ha 20 65 Pre-emergence Barley, spring 0 0 Barley, winter 0 0 Black grass 0 13 Gallium 78 13 Kochia 7 12 Oats, Wild 22 28 Rapeseed0 0 Wheat, spring0 63 Wheat, winter0 23 TEST E Seeds of selected plant species of grain (Zea mays), soybean (Glycine max), velvet mallow (Abutilon theophrastí), white quinoa (Chenopodium album), poinsettia, wild (Euphorbia heterophylla), red pigweed, palm (Amaranthus palmera! ), hemp (common hemp, Amaranthus rudis), Suriname grass (Brachiaria decumbens), crabgrass, Grande (Digitada sanguínalis), crabgrass, Brazil (Digitana horizontalis), panicum, autumn (Panicum dichotomiflorum), foxtail, giant (Setaria faberü), foxtail, green (Setaria viridis), goosefoot grass (Eleusine indica), Johnson grass (Sorgo halepense), ragweed (ragweed, Ambrosia elatior), barn (Echinochloa crus-galli), huizapol (Southern huizapol, Cenchrus echinatus), arrowleaf sida (Sida rhombífolia), ryegrass, Italiana (Lolium multiflorum), dayflower, VA (Virginia (VA) dayflower, Commelina virginica), Lesser field bindweed (Convolvulus arvensis), morning glory (Ipomoea coccinea), horseweed (Conyza canadensis), kochia (Kochia scoparia), chives, Yellow (Cyperus esculentus) and downy leafy Bidens (Bidens pilosa), were planted in a silt loam and treated in pre-emergency with test chemicals formulated in a non-phytotoxic solvent mixture that included a surfactant. At the same time, selected plants of these crops and weed species and also waterhemp_RES1, (ALS & Triazine resistant common hemp, Amaranthus rudis), and waterhemp_RES2, (ALS & HPPD resistant common hemp, Amaranthus rudis) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat moss, vermiculite, wetting agent and starter nutrients were treated with post-emergence applications of formulated test chemicals from the same way. Plants ranged in height from 2 to 18 cm for postemergence treatments (1 to 4 leaf stage). Treated and control plants were kept in a greenhouse for 14 to 21 d, after which time all species were compared with controls and evaluated visually. Plant response ratings, summarized in Table E, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. ncccnn / i ζπζ / β / υιλι Table E Compounds 125 g ai / ha20 65 post emergency Arrow Blade Aids75 Barn- 95 Table E Composites g ai / ha20 65 post emergency Arrow sheet Sida70 Barn- 93 Leafy Bidens 100 Leafy Bidens 95 Corn 10 35 Corn 10 23 Crab grass, Brazil Crab Grass, Large -35 Crab Grass, Brazil 60 Crab Grass, Large Dayflower, VA 70 - Dayflower, VA 60 - Lesser Field Bindweed 90 - Lesser Field Bindweed 90 Foxtail, Giant - 95 Foxtail, Giant - 90 Horsegrass 80 85 Horsegrass 85 85 Kochia 90 - Kochia 80 - Panicum, Autumn 95 93 Panicum, Autumn 90 93 Red Pigweed, Palm 60 55 Red Pigweed, Palm 70 68 Poinsettia, Wild 50 - Poinsettia, Wild 40 - Ragweed 95 93 Ragweed 95 95 Ryegrass , Italian 90 - Ryegrass, Italian 85 - Huizapol 85 - Huizapol 70 - Soybean 40 93 Soybean 30 90 Suriname Grass - 93 Suriname Grass - 85 Velvet Mauve - 90 Velvet Mauve - 85 Hemp 90 97 Hemp 95 99 Waterhemp_RES1 95 - Waterhemp_RES1 8 0 - Waterhemp_RES2 70 - Waterhemp_RES2 60 - Table E Composites Table E Composites 31 g ai / ha 20 65 16 g ai / ha 20 65 Post-emergence Arrow sheet Sida 70 - Post-emergence Arrow sheet Sida 60 - Barn - 88 Barn - 80 Bidens leafy 95 - Bidens leafy 90 Maize 20 20 Maize 5 0 Crabgrass, Brazil 40 - Crabgrass, Brazil 20 - Crabgrass, Large - 13 Crabgrass, Large - 10 Dayflower, VA 50 - Dayflower, VA 30 - Lesser field bindweed 90 - Lesser field bindweed 75 - Foxtail, Giant - 88 Foxtail, Giant - 70 Horsegrass 75 75 Horsegrass 80 65 Kochia 75 - Kochia 80 - Panicum, autumn 90 88 Panicum, Autumn 70 80 Red Pigweed, Palm 65 43 Red Pigweed, Palm 60 35 Poinsettia, Wild 50 - Poinsettia, Wild 20 - Ragweed 85 93 Ragweed 90 95 Ryegrass, Italian 80 - Ryegrass, Italian 70 - Huizapol 60 - Huizapol 60 - ncccnn / i ζπζ / β / υ Soybean 15 80 Soybean 10 70 Suriname Grass - 78 Suriname Grass - 73 Velvet Mallow - 90 Velvet Mallow - 75 Hemp 75 88 Hemp 75 83 Waterhemp_RES1 90 - Waterhemp_RES1 75 - Waterhemp_RES2 40 - Waterhemp_RES2 15 - Table E Compounds Table E Compounds 125g ai / ha Prior to emergence 20 65 62 g ai / ha Prior to emergence 20 65 Sida arrow sheet 85 - Sida arrow sheet 80 - Barn 100 60 Barn 80 38 Leafy Bidens 100 - Leafy Bidens 95 Maize 0 43 Maize 0 20 Crabgrass, Brazil 100 - Crabgrass, Brazil 100 - Crabgrass, Large 80 48 Crabgrass, Large 75 38 Dayflower, VA 5 - Dayflower, VA 0 - Lesser field bindweed 100 - Lesser field bindweed 90 Foxtail, Giant 98 100 Foxtail, Giant 90 90 Foxtail, Green 100 - Foxtail, Green 100 - Goosefoot Grass 75 - Goosefoot Grass 30 - Horsegrass -100 Horsegrass -100 Johnson Grass 50 - Kochia 70 - Kochia 85 - White Quinoa 98 - White Quinoa 100 - Bells 60 - Bells 100 - Chives, Yellow 75 - Chives, Yellow 75 - Panicum, fall 98 100 Panicum, fall 100 99 Red pigweed, Palm tree 95 80 Red pigweed, Palm 98 90 Poinsettia, Wild 0 - Poinsettia, Wild 0 - Ragweed 95 100 Ragweed 98 100 Ryegrass, Italiana 98 - Ryegrass, Italiana 95 - Huizapol 85 - Huizapol 90 - Soybean 15 15 Soybean 0 43 Suriname Grass 90 85 Suriname Grass 100 100 Velvet Mauve 90 100 Velvet Mauve Hemp 100 100 100 99 Hemp 98 99 ncccnn / i 7Π7 / β / υ Table E Composites 31 g ai / ha Pre-emergence 20 65 Arrowleaf Sida 90 - Barn 75 40 Bidens frondosa 90 - Maize 0 5 Crabgrass, Brazil 90 - Crabgrass, Large 65 18 Dayflower, VA 0 - Morning Glory Minor Field 85 - Foxtail, Giant 60 78 Foxtail, Green 80 - Goosefoot Grass 0 - Horsegrass - 100 Johnson Grass 0 - Kochia 50 - White Quinoa 95 - Bluebells 20 - Chives, Yellow 15 - Panicum , Autumn 98 99 Red Pigweed, Palm Tree 35 58 Poinsettia, Wild 0 - Ragweed 95 99 Ryegrass, Italian 25 - Huizapol 75 - Soybean - 13 Suriname Grass 80 92 Velvet Mauve Hemp 70 90 80 100 Table E Composites 16 g ai / ha 20 65 Pre-emergence Arrowleaf Sida 90 - Barn 0 0 Bidens frondosa 20 - Maize 0 0 Crabgrass, Brazil 75 - Crabgrass, Large 65 45 Dayflower, VA 0 - Morning Glory minor field 5 - Foxtail, Giant 10 5 Foxtail, Green 35 - Goosefoot Lawn 0 - Horsegrass - 100 Johnson Grass 0 - Kochia 0 - White Quinoa 80 - Bluebells 10 - Chives, Yellow 10 - Panicum , Autumn 75 75 Red Pigweed, Palm 20 40 Poinsettia, Wild 0 - Ambrosia 60 75 Ryegrass, Italian 0 - Huizapol 30 - Soybean 0 23 Suriname Grass 35 8 Velvet Mauve 50 75 Hemp 60 75 ncccnn / i ζπζ / β / υ TEST F Three plastic pots (approx. 16 cm diameter) per ratio were partially filled with sterilized Tama silt loam comprising a 35:50:15 ratio of sand, silt, and clay and 2.6% organic matter. The separate plantings for each of the three pots were as follows. Seeds from the U.S.A. of monochoria (Monochoria vaginalis), nutshell, umbrella (small-flowered umbrella nut, Cyperus difformis) and mugwort (purple mugwort, Ammannia coccinea), were planted in a 16-cm pot for each proportion. The seeds of the U.S.A. of rice marsh chives (Cyperus iria), purple grass, Brdd. (purple bearded grass, Leptochloa fascicularís), a row of 9-10 water-seeded rice seedlings (Rice, W.S. Jap, Oryza sativa cv. 'Japonica - M202' or rice, W.S. Ind, 'Indica'), and two rows of 3 or 4 transplanted rice seedlings {Oryza sativa cv. ‘Japonica - M202j were planted in a 16 cm pot for each proportion. The seeds of the U.S.A. barn grass (Echinochloa crus-galli), and Itima aquatic grass (Echinochloa oryzicola) were planted in a 16 cm pot for each proportion. Plantings were sequential so that the crop and weed species were at the 2.0 to 2.5 leaf stage at the time of treatment. Potted plants were grown in a greenhouse with day / night temperature settings of 30 / 27°C, and supplemental balanced lighting was provided to maintain a 16-h photoperiod. The test pots were kept in the greenhouse until the completion of the test. At the time of treatment, the test pots were flooded to 3 cm above the soil surface, treated by applying test compounds directly to the paddy water, and then kept in that depth of water for the duration of the treatment. the proof. The effects of the treatments on rice and weeds were evaluated visually in comparison with untreated controls after 21 d. Plant response ratings, summarized in Table F, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. ncccnn / i ζηζ / Β / γ Table F Composite 250 g ai / ha 20 Flood Barn 65 Weed Chives 100 Monochoria 99 Sagebrush 99 Rice, Transplanted 0 Rice, Seeded with water 23 Coquillo, Umbrella 100 Purple Grass, Brdd. Aquatic Grass, Last 73 Table F Composite 125 g ai / ha 20 65 Flood Barn 43 60 Marsh Chives 97 Monochoria 95 100 Sagebrush 92 Rice, Transplanted 0 15 Rice, Water Seed 5 0 Coquillo, Umbrella 95 Purple Grass, Brdd. - 100 Aquatic Grass, Last 50 55 Table F Composite 62 g ai / ha 20 Barn Flood 0 Marsh Chives 85 Table F 64 g ai / ha Barn Flood Monochoria Composite 65 10 100 Table F Composite 31 g ai / ha 20 Barn Flood 0 Marshland Chives 70 Monochona 90 Rice, Transplanted 0 Monochona 10 Sagebrush 0 Rice, Seeded with water 0 Sagebrush 0 Rice, Transplanted 0 Purple grass, Brdd. 98 Rice, Transplanted 0 Rice, Planted with water 0 Coquillo, Umbrella 60 Purple grass, Brdd. Aquatic Grass, Last 35 Aquatic Grass, Last 20 Rice, Seed with Water 0 Nut Nut, Umbrella 0 Purple Grass, Brdd. Aquatic Grass, Last 0 ncccnn / i ζηζ / Β / γ TEST G This test evaluated the effect of mixtures of Com. No. 20 with (b15C1) on various plant species. Seeds of selected plant species of maize (ZEAMD; Zea mays, cv. 'Pioneer 1184'), soybean (GLXMA; Glycine max, cv. Pioneer 35T58), giant foxtail (SETFA; Setaria faberi), barn (ECHCG ; Echinochloa crus-galli), large crabgrass (DIGSA; Dígitaria sanguínalís), amaranth palm (AMAPA; Amaranthus palmeral), common hemp (AMATU; Amaranthus rudis), and ragweed (AMBEL; Ambrosia artemisiifolia) were planted in pots containing Tama and silt loam were treated pre-emergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture that included a surfactant. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 d, after which time all treated plants were compared to untreated controls and visually assessed for lesions. Plant response ratings, summarized in Table G, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Test results are presented as a mean of 4 replicates. Table G - Observed Results of Com. No. 20 Alone and in Combination with (b15C1)* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA ECHCG DIGSA Com. No. 20 (b15C1) 62 - 0 24 74 70 25 31 - 0 18 88 51 11 16 - 0 0 66 21 9 - 31 0 0 74 35 100 - 16 0 0 34 0 90 — 8 0 0 5 0 54 62 31 0 16 100 94 100 62 16 0 26 100 94 96 62 8 0 26 100 76 69 31 31 0 11 100 82 83 Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA ECHCG DIGSA Com. No. 20 (b15C1) 31 16 0 9 100 75 79 31 8 0 4 100 71 50 16 31 0 5 100 74 93 16 16 0 0 100 53 59 16 8 8 0 94 44 16 ncccnn / i 7Π7 / Β / Υ Application Rate (g a.i. / ha) AMAPA AMBEL AMATU Com. No. 20 (b15C1) 62 - 74 99 78 31 — 73 96 70 16 — 48 55 73 - 31 100 20 97 — 16 90 0 88 — 8 54 0 60 62 31 100 93 100 62 16 100 99 96 62 8 88 94 86 31 31 99 95 95 31 16 100 86 93 31 8 90 82 83 16 31 99 83 95 16 16 94 75 94 16 8 84 83 74 Application Rates are grams of active ingredient per hectare (g a.i. / ha). H-TEST This test evaluated the effect of mixtures of Com. No. 20 with atrazine or glyphosate on various plant species. The seeds of selected plant species of maize (ZEAMD; Zea mays, cv. 'Pioneer 1184'), soybean (GLXMA; Glycine max, cv. Pioneer 35T58), giant foxtail (SETFA; Setaria faberi), Suriname grass ( BRADC; Brachiaria decumbens), autumn panicum (PANDI; Panicum dichotomiflorum), velvet mallow (ABUTH; Abutilon threeophrasti), mare's tail (ERICA; Conyza canadensis), barn (ECHCG; Echinochloa crus-galli), large crabgrass (DIGSA ; Fingered sanguinalis), amaranth palm (AMAPA; Amaranthus palmeral), common hemp (AMATU; Amaranthus rudis), E. black nightshade (SOLPT; Solanum ptycanthum), and common ragweed (AMBEL; Ambrosia artemisiifolia) were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat moss, vermiculite, wetting agent and starter nutrients and post-emergence treated using test chemicals formulated in a mixture of non-phytotoxic solvent that included a surfactant. Plants ranged in height from 2 to 10 cm and were at the one to two leaf stage by post-emergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 14 d, after which time all treated plants were compared to untreated controls and visually assessed for lesions. Plant response ratings, summarized in Tables H1 and H2, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Test results are presented as a mean of 4 replicates. ncccnn / i 7Π7 / Β / Υ Table H1 - Observed Results of Com. No. 20 Alone and in Combination with Atrazine* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA ECHCG DIGSA Com. No. 20 Atrazine 125 - 0 18 80 100 36 62 - 0 21 79 100 29 31 - 0 30 71 100 34 - 250 0 33 0 100 0 — 125 0 15 0 96 0 125 250 0 63 98 78 7 3 125 125 0 44 97 100 60 62 250 0 53 98 100 44 62 125 0 49 91 100 40 31 250 0 59 88 100 34 31 125 0 38 83 96 29 Application Rate (g a.i. / ha) ERICA AMATU AMBEL AMAPA ABUTH Com. No. 20 Atrazine 125 - 88 80 98 54 94 62 - 85 80 94 36 89 31 - 85 70 89 10 76 - 250 83 39 80 74 10 — 125 23 30 48 76 0 125 250 97 96 10 0 99 100 125 125 94 98 100 98 100 Application Rate (g a.i. / ha) ERICA AMATU AMBEL AMAPA ABUTH Com. No. 20 Atrazine 62 250 98 98 100 89 100 62 125 93 97 100 94 98 31 250 99 86 98 85 100 31 125 91 93 99 86 98 ncccnn / i znz / B / v Application Rate (g a.i. / ha) PANDI SOLPT BRADC Com. No. 20 Atrazine 125 - 89 95 93 62 — 84 93 84 31 — 73 86 73 - 250 0 64 0 — 125 0 28 0 125 250 95 100 94 125 125 89 100 94 62 250 89 100 84 62 125 86 99 81 31 250 74 100 74 31 125 70 99 73 Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table H2 - Observed Results of Com. No. 20 Alone and in Combination with Glyphosate* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA ECHCG DIGSA Com. No. 20 Glyphosate 125 - 0 18 80 100 36 62 - 0 21 79 100 29 31 - 0 30 71 100 34 - 125 74 25 75 31 90 — 62 68 10 74 6 86 125 125 76 29 7 8 69 84 125 62 54 24 80 65 55 62 125 75 15 75 51 89 62 62 55 13 75 50 61 Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA ECHCG DIGSA Com. No. 20 Glyphosate 31 125 75 23 73 30 89 31 62 58 24 73 25 65 ncccnn / i 7Π7 / Β / Υ Application Rate (g a.i. / ha) ERICA AMATU AMBEL AMAPA ABUTH Com. No. 20 Glyphosate 125 - 88 80 98 54 94 62 - 85 80 94 36 89 31 - 85 70 89 10 76 - 125 0 25 84 23 15 — 62 0 11 68 43 0 125 125 89 94 88 58 84 125 62 90 91 95 53 95 62 125 86 71 88 58 85 62 62 88 76 86 48 93 31 125 85 59 85 40 78 31 62 85 64 80 28 81 Application Rate (g a.i. / ha) PANDI SOLPT BRADC Com. No. 20 Glyphosate 125 - 89 95 93 62 — 84 93 84 31 — 73 86 73 - 125 51 51 69 — 62 28 43 68 125 125 89 95 91 125 62 89 95 86 62 125 84 9 3 86 62 62 75 93 74 31 125 66 94 84 31 62 56 93 73 Application Rates are grams of active ingredient per hectare (g a.i. / ha). TEST I This test evaluated the effect of mixtures of Com. No. 20 with saflufenacil or pyroxasulfone on various plant species. The seeds of selected plant species of maize (ZEAMD; Zea mays, cv. 'Pioneer 1184'), soybean (GLXMA; Glycine max, cv. Pioneer 35T58), giant foxtail (SETFA; Setaria faberí), amaranth palm (AMAPA ; Amaranthus palmera!), common hemp (AMATU; Amaranthus rudis), mare's tail (ERICA; Conyza canadensis), and ragweed (AMBEL; Ambrosia artemisiifolia) were planted in pots containing Tama loam soil and treated prior to emergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture that included a surfactant. At the same time, selected plants of these crops and weed species were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat moss, vermiculite, starting wetting agent and nutrients and post-emergence treated with test chemicals formulated in the same way. Plants ranged in height from 2 to 10 cm and were at the one to two leaf stage by post-emergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 14-21 d, after which time all treated plants were compared to untreated controls and visually assessed for lesions. Plant response ratings, summarized in Tables 11 through I4, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Test results are presented as a mean of 4 replicates. Table 11 - Observed Pre-Emergency Results of Com. No. 20 Alone and in Combination with Saflufenacil* ncccnn / i 7Π7 / Β / Υ Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Saflufenacil 62 - 0 0 99 61 80 31 - 0 0 84 23 0 16 - 0 0 39 44 0 8 - 0 0 25 23 0 - 8 0 0 0 88 84 — 4 0 0 0 35 55 62 8 0 0 99 96 99 62 4 0 0 97 85 83 31 8 0 0 93 100 89 31 4 0 0 86 86 66 Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Saflufenacil 16 8 0 0 74 100 100 16 4 0 0 74 63 60 8 8 0 0 16 100 68 8 4 0 0 15 55 38 ncccnn / i znz / B / v Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Saflufenacil 62 - 98 100 31 — 69 100 16 — 10 100 8 — 0 93 — 8 100 100 — 4 96 94 62 8 100 100 62 4 90 100 31 8 100 100 31 4 28 100 16 8 89 100 16 4 49 100 8 8 100 100 8 4 96 100 * Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table I2- Observed Pre-Emergency Results of Com. No. 20 Alone and in Combination with Pyroxasulfone* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Pyroxasulfone 62 - 0 0 99 61 80 31 - 0 0 84 23 0 16 - 0 0 39 44 0 8 — 0 0 25 23 0 Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Pyroxasulfone — 8 0 0 98 38 45 — 4 0 0 76 0 5 62 8 0 0 100 91 100 62 4 0 0 100 98 92 31 8 0 0 100 75 76 31 4 0 0 99 90 64 16 8 0 0 97 73 60 16 4 0 0 97 46 70 8 8 0 0 98 63 74 8 4 0 0 97 51 44 ncccnn / i ζπζ / β / υ Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Pyroxasulfone 62 - 98 100 31 — 69 100 16 — 10 100 8 — 0 93 - 8 0 100 — 4 0 79 62 8 88 100 62 4 96 100 31 8 100 100 31 4 90 100 16 8 73 100 16 4 31 100 8 8 25 100 8 4 0 100 Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table I3 - Observed Post-Emergency Results of Com. No. 20 Alone and in Combination with Saflufenacil* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Saflufenacil 62 - 0 16 78 65 83 31 - 0 15 76 50 81 16 — 0 0 80 40 59 8 — 0 0 55 38 50 - 8 70 91 55 70 90 — 4 15 74 23 84 85 62 8 7 5 96 97 96 98 62 4 63 90 93 86 95 31 8 69 95 94 98 98 31 4 36 90 83 83 298 16 8 74 95 91 100 100 16 4 15 91 74 93 86 8 8 65 91 75 93 91 8 4 15 90 60 85 93 ncccnn / i 7Π7 / Ε / Υ Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Saflufenacil 62 - 94 90 31 — 100 90 16 — 90 86 8 — 86 85 - 8 100 100 — 4 100 95 62 8 100 100 62 4 100 100 31 8 100 100 31 4 100 93 16 8 100 100 16 4 100 98 8 8 100 96 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Saflufenacil 8 4 100 95 ncccnn / i 7Π7 / Β / Υ * Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table I4 - Observed Post-Emergency Results of Com. No. 20 Alone and in Combination with Pyroxasulfone* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Pyroxasulfone 62 - 0 16 78 65 83 31 — 0 15 76 50 81 16 — 0 0 80 40 59 8 — 0 0 55 38 50 - 8 0 15 6 0 0 — 4 0 0 0 15 0 62 8 0 20 80 73 80 62 4 28 19 83 61 81 31 8 0 23 76 63 76 31 4 0 15 76 50 66 16 8 0 20 74 48 60 16 4 0 15 73 43 68 8 8 0 14 73 45 6 3 8 4 0 0 60 51 60 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Pyroxasulfone 62 - 94 90 31 — 100 90 16 — 90 86 8 — 86 85 - 8 24 0 — 4 0 0 62 8 99 93 62 4 97 89 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Pyroxasulfone 31 8 94 90 31 4 97 85 16 8 91 89 16 4 91 88 8 8 85 86 8 4 85 85 ncccnn / i znz / B / v * Application Rates are grams of active ingredient per hectare (g a.i. / ha). TEST This test evaluated the effect of mixtures of Com. No. 20 with (b15C2) on various plant species. The seeds of selected plant species of maize (ZEAMD; Zea mays, cv. 'Pioneer 1184'), soybean (GLXMA; Glycine max, cv. Pioneer 35T58), giant foxtail (SETFA; Setaria faberí), amaranth palm (AMAPA ; Amaranthus palmeral), common hemp (AMATU; Amaranthus rudis), horsetail (ERICA; Conyza canadensis), and common ragweed (AMBEL; Ambrosia artemisiifolia) were planted in pots containing Tama loam soil and treated prior to planting. emergency with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture that included a surfactant. At the same time, selected plants of these crops and weed species were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat moss, vermiculite, wetting agent and starter nutrients and treated post-emergence with test chemicals formulated in the same manner. Plants ranged in height from 2 to 10 cm and were at the one to two leaf stage during postemergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 14-21 d, after which time all treated plants were compared to untreated controls and visually assessed for lesions. Plant response ratings, summarized in Tables J1 and J2, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Test results are presented as a mean of 4 replicates. Table J1 - Observed Pre-Emergency Results of Com. No. 20 Alone and in Combination with (b15C2)* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 (b15C2) 62 - 0 20 89 60 50 Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 (b15C2) 31 - 0 0 78 48 29 16 - 0 0 63 46 20 8 - 0 0 15 20 0 — 62 0 0 100 100 100 — 31 0 0 95 100 100 — 16 0 0 64 90 79 — 8 0 0 8 63 20 62 62 0 20 100 100 100 62 31 0 5 100 100 100 62 16 0 31 100 100 100 62 8 0 9 100 89 94 31 62 0 8 100 100 99 3 1 31 0 21 100 96 100 31 16 0 29 100 96 100 31 8 0 19 100 99 94 16 62 0 25 100 86 100 16 31 0 9 100 100 100 16 16 0 5 100 100 96 16 8 0 27 94 90 81 8 6 2 0 3 100 99 100 8 31 0 0 100 100 100 8 16 0 13 98 100 93 8 8 0 15 75 89 80 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 (b15C2) 62 - 96 95 31 - 86 94 16 - 100 90 8 — 0 58 - 62 15 13 — 31 0 0 ncccnn / i 7Π7 / β / υ Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 (b15C2) — 16 0 0 — 8 0 0 62 62 100 99 62 31 100 77 62 16 100 63 62 8 100 99 31 62 98 97 31 31 100 93 31 16 100 99 31 8 88 97 16 62 53 99 16 31 0 93 16 16 89 88 16 8 33 87 8 62 0 94 8 31 0 85 8 16 0 0 8 8 16 63 ncccnn / i 7Π7 / Β / Υ * Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table J2 - Observed Post-Emergency Results of Com. No. 20 Alone and in Combination with (b15C2)* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 (b15C2) 62 - 0 6 80 63 86 31 - 0 9 75 33 71 16 - 0 4 69 15 53 8 - 0 3 34 18 55 - 62 10 68 6 74 83 - 31 9 43 8 56 75 - 16 5 29 5 38 55 — 8 3 20 5 20 43 62 62 15 79 91 92 98 Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 (Ó15C2) 62 31 8 51 90 86 95 62 16 15 51 91 78 94 62 8 1 38 86 65 91 31 62 10 75 93 84 95 31 31 6 45 85 73 90 31 16 11 54 86 64 91 31 8 3 39 78 55 84 16 62 13 76 81 78 94 16 31 6 46 80 64 89 16 16 8 58 76 60 86 16 8 1 39 71 54 81 8 62 13 68 80 84 88 8 31 11 48 75 63 67 8 16 1 45 76 59 85 8 8 0 33 63 46 68 ncccnn / i ζπζ / β / υ Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 (b15C2) 62 - 95 90 31 — 91 90 16 — 93 90 8 — 86 85 - 62 20 5 — 31 10 0 — 16 3 0 — 8 5 0 62 62 98 90 62 31 97 89 62 16 97 90 62 8 97 90 31 62 97 90 31 31 95 90 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 (b15C2) 31 16 95 89 31 8 94 90 16 62 90 88 16 31 94 90 16 16 85 90 16 8 90 86 8 62 85 85 8 31 81 85 8 16 83 86 8 8 84 85 ncccnn / i znz / B / v * Application Rates are grams of active ingredient per hectare (g a.i. / ha). TEST K This test evaluated the effect of mixtures of Com. No. 20 with metribuzin or rimsulfuron on various plant species. Seeds of selected plant species of maize (ZEAMD; Zea mays, cv. 'Pioneer 1184j), soybean (GLXMA; Glycine max, cv. Pioneer 35T58), giant foxtail (SETFA; Setaria faberi), amaranth palm (AMAPA; Amaranthus palm grove), common hemp (AMATU; Amaranthus rudis), mare's tail (ERICA; Conyza canadensis), and common ragweed (AMBEL; Ambrosia artemisiifolia) were planted in pots containing Tama Silt Loam Earth and treated prior to emergence with a directed soil spray using test chemicals formulated in a non-phytotoxic solvent mixture that included a surfactant. At the same time, selected plants of these crops and weed species were planted in pots containing Redi-Earth® planting medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat moss, vermiculite, starting wetting agent and nutrients and post-emergence treated with test chemicals formulated in the same way. Plants ranged in height from 2 to 10 cm and were at the one- to two-leaf stage for post-emergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 14-21 d, after which time all treated plants were compared to untreated controls and visually assessed for lesions. Plant response ratings, summarized in Tables K1 through K4, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Test results are presented as a mean of 4 replicates. Table Κ1 - Pre-emergence results observed from Com. No. 20 Alone and in Combination with Metribuzin* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Metribuzin 62 - 0 0 100 45 30 31 - 0 0 84 50 20 16 — 0 0 50 26 0 8 — 0 0 6 0 0 - 125 0 0 80 70 86 — 62 0 0 30 78 53 62 125 0 0 100 68 100 62 62 0 0 100 49 100 31 125 0 0 100 98 100 31 62 0 0 99 70 83 16 125 0 0 98 100 100 16 62 0 0 88 95 78 8 125 0 0 95 91 98 8 62 0 0 65 66 71 ncccnn / i 7Π7 / Β / Υ Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Metribuzin 62 - 100 100 31 — 55 100 16 — 26 100 8 — 0 89 - 125 100 100 — 62 40 100 62 125 100 100 62 62 100 100 31 125 100 100 31 62 100 100 16 125 100 100 16 62 75 100 8 125 100 100 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Metribuzin 8 62 100 100 ncccnn / i ζηζ / Β / γ * Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table K2 - Observed Pre-Emergency Results of Com. No. 20 Alone and in Combination with Rimsulfuron* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Rimsulfuron 62 - 0 0 100 45 30 31 — 0 0 84 50 20 16 — 0 0 50 26 0 8 — 0 0 6 0 0 - 16 0 0 73 40 73 — 8 0 0 50 33 51 62 16 0 0 100 51 63 62 8 0 0 98 65 70 31 16 0 0 90 53 53 31 8 0 0 93 40 74 16 16 0 0 83 28 43 16 8 0 0 66 31 41 8 16 0 0 14 0 0 8 8 0 0 36 35 39 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Rimsulfuron 62 - 100 100 31 — 55 100 16 — 26 100 8 — 0 89 - 16 43 98 — 8 0 95 62 16 100 100 62 8 100 100 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Rimsulfuron 31 16 95 100 31 8 99 100 16 16 86 100 16 8 78 95 8 16 14 93 8 8 48 100 ncccnn / i znz / B / v * Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table K3 - Observed Post-Emergency Results of Com. No. 20 Alone and in Combination with Metribuzin* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Metribuzin 62 - 0 13 92 60 62 31 — 0 8 77 33 68 16 — 0 0 62 38 57 8 — 0 0 37 28 50 — 125 10 53 10 47 82 — 62 0 33 0 35 37 62 125 18 40 98 75 90 62 62 13 32 100 80 92 31 125 15 52 98 77 85 31 62 10 37 97 58 100 16 125 7 55 93 77 88 16 62 7 40 98 57 92 8 125 10 33 82 80 83 8 62 0 27 78 65 80 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Metribuzin 62 - 97 93 31 - 92 92 16 — 82 85 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Metribuzin 8 - 82 77 — 125 62 13 — 62 55 10 62 125 99 100 62 62 99 99 31 125 99 97 31 62 99 98 16 125 100 100 16 62 99 90 8 12 5 83 80 8 62 99 100 ncccnn / i 7Π7 / Β / Υ * Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table K4 - Observed Post-Emergency Results of Com. No. 20 Alone and in Combination with Rimsulfuron* Application Rate (g a.i. / ha) ZEAMD GLXMA SETFA AMAPA AMATU Com. No. 20 Rimsulfuron 62 - 0 13 92 60 62 31 — 0 8 77 33 68 16 — 0 0 62 38 57 8 — 0 0 37 28 50 — 16 10 93 97 60 77 — 8 0 75 80 60 75 62 16 3 92 100 63 77 62 8 0 85 99 62 75 31 16 0 83 99 58 60 31 8 0 90 97 60 75 16 16 0 85 95 53 75 16 8 0 90 97 55 63 8 16 0 7 42 25 50 8 8 0 90 95 60 68 100 Application Rate (g a.i. / ha) AMBEL ERICA Com. No. 20 Rimsulfuron 62 - 97 93 31 — 92 92 16 — 82 85 8 — 82 77 — 16 60 70 — 8 40 50 62 16 94 97 62 8 97 96 31 16 90 92 31 8 96 95 16 16 92 92 16 8 87 83 8 16 82 82 8 8 80 68 Application Rates are grams of active ingredient per hectare (g a.i. / ha). TEST L ncccnn / i 7Π7 / Β / Υ This test evaluated the effect of mixtures of Com. No. 20 with benoxacor, isoxadifen-ethyl, or cloquintocet-mexyl on various plant species. The seeds of selected plant species of maize (ZEAMD; Zea mays, cv. 'Pioneer 1184'), soybean (GLXMA; Glycine max, cv. Pioneer 35T58), winter wheat (TRZAW; Triticum aetivum, cv. Arezzo), rice (ORYSS; Oryza sativa, cv. M202), and giant foxtail (SETFA; Setaria faberi) were planted in pots containing RediEarth® seed medium (Scotts Company, 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat, vermiculite, wetting agent and starter nutrients and treated post-emergence using test chemicals formulated in a non-phytotoxic solvent mixture including a surfactant. Plants ranged in height from 7 to 10 cm and were at the one- to two-leaf stage for post-emergence treatment. Treated plants and untreated controls were maintained in a greenhouse for approximately 14 d, after which time all treated plants were compared to untreated controls and visually assessed for lesions. Plant response ratings, summarized in Tables L1 through L3, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Test results are presented as a mean of 4 replicates. 101 Table L1 - Observed Results of Com. No. 20 Alone and in Combination with Benoxacor* Application Rate (g a.i. / ha) ZEAMD GLXMA TRZAW ORYSS SETFA Com. No. 20 Benoxacor 375 - 34 39 39 23 90 250 — 1 29 36 18 88 125 — 8 15 28 5 84 - 31 0 0 0 0 0 375 31 15 45 35 25 93 250 31 19 39 31 24 90 125 31 13 20 18 8 90 * Application Rates are grams of active ingredient per hectare (g a.i. / ha). ncccnn / i znz / B / v Table L2 - Observed Results of Com. No. 20 Alone and in Combination with Isoxadifen-ethyl* Application Rate (g a.i. / ha) ZEAMD GLXMA TRZAW ORYSS SETFA Com. No. 20 Isoxadiphenethyl 375 - 34 39 39 23 90 250 — 1 29 36 18 88 125 — 8 15 28 5 84 - 31 0 10 0 8 0 375 31 0 45 28 6 97 250 31 0 45 10 0 93 125 31 0 29 0 0 88 * Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table L3 - Observed Results of Com. No. 20 Alone and in Combination with Cloquintocet-mexyl* Application Rate (g a.i. / ha) ZEAMD GLXMA TRZAW ORYSS SETFA Com. No. 20 Cloquintocethmexyl 375 - 34 39 39 23 90 250 - 1 29 36 18 88 125 — 8 15 28 5 84 - 31 0 0 0 0 0 375 31 0 43 23 29 96 250 31 0 31 21 2 5 91 102 Application Rate (g a.i. / ha) ZEAMD GLXMA TRZAW ORYSS SETFA Com. No. 20 Cloquintocethmexyl 125 31 0 25 0 10 93 * Application Rates are grams of active ingredient per hectare (g a.i. / ha). ncccnn / i znz / B / v TEST M This test evaluated the effect of mixtures of Com. No. 20 with isoxadifen-ethyl, or cloquintocetmexil, or Mefenpyr-diethyl on various plant species. The seeds of selected plant species of maize (ZEAMD; Zea mays, cv. 'Pioneer 1184j, soybean (GLXMA; Glycine max, cv. Pioneer 35T58), winter wheat (TRZAW; Triticum aetivum, cv. Arezzo), winter barley (HORVW; Hordeum vulgare, cv. Boone), rice (ORYSS; Oryza sativa, cv. M202), and giant foxtail (SETFA; Setaria faberi) were planted in pots containing Redi-Earth® seed medium (Scotts Company , 14111 Scottslawn Road, Marysville, Ohio 43041) comprising sphagnum peat moss, vermiculite, wetting agent, and starter nutrients and were post-emergence treated using test chemicals formulated in a non-phytotoxic solvent mixture that included a surfactant. Plants ranged in height from 7 to 10 cm and were at the one- to two-leaf stage for post-emergence treatment.Treated and untreated control plants were maintained in a greenhouse for approximately 14 d, after which time all plants were grown. Treated plants were compared to untreated controls and visually assessed for lesions. Plant response ratings, summarized in Tables M1 through M3, are based on a scale of 0 to 100 where 0 is no effect and 100 is complete control. A dash (-) response means no test result. Test results are presented as a mean of 3 replicates. Table M1 - Observed Results of Com. No. 20 Alone and in Combination with Isoxadifen-ethyl* Application Rate (g a.i. / ha) ZEAMD GLXMA TRZAW HORVW ORYSS SETFA Com. No. 20 Isoxadiphenethyl 375 - 33 35 35 20 40 100 250 — 28 30 22 15 40 100 125 — 17 22 8 10 35 99 62 — 0 15 0 0 20 96 - 31 0 0 0 0 0 0 375 31 0 40 23 12 43 98 250 31 0 38 13 12 35 99 125 31 0 30 0 7 18 98 62 31 0 20 0 0 15 93 103 * Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table M2 - Observed Results of Com. No. 20 Alone and in Combination with Cloquintocet-mexyl* Application Rate (g a.i. / ha) ZEAMD GLXMA TRZAW HORVW ORYSS SETFA Com. No. 20 Cloquintocethmexyl 375 - 33 35 35 20 40 100 250 - 28 30 22 15 40 100 125 - 17 22 8 10 35 99 62 - 0 15 0 0 20 96 - 31 0 0 0 0 0 0 375 31 0 60 8 13 55 100 250 31 0 40 0 15 42 100 125 31 0 22 0 13 33 98 62 31 0 17 0 12 10 93 * Application Rates are grams of active ingredient per hectare (g a.i. / ha). Table M3 - Observed Results of Com. No. 20 Alone and in Combination with Mefenpyr-diethyl* ncccnn / i znz / B / v Application Rate (g a.i. / ha) ZEAMD GLXMA TRZAW HORVW ORYSS SETFA Com. No. 20 Mefenpyrdiethyl 375 - 33 35 35 20 40 100 250 - 28 30 22 15 40 100 125 - 17 22 8 10 35 99 62 — 0 15 0 0 20 96 - 31 0 0 0 0 0 0 375 3 1 22 57 12 10 58 99 250 31 13 35 3 3 40 99 125 31 7 17 0 12 35 99 62 31 5 25 0 0 17 93 * Application Rates are grams of active ingredient per hectare (g a.i. / ha).
Claims
1. A compound of Formula I and / V-oxides or salts thereof, characterized in that R1 is C1-C4 alkyl or Cs-Ce cycloalkyl; R2 is H, Cl, Bro I; R3 is Cl or OR4; R4 is H or C1-C4 alkyl; R5 is H, F, Cl or CH3; and Rs is H or Cl.
2. The compound according to claim 1, characterized in that R2 is Cl; R3 is OR4; R4 is H or methyl; and R5 is F, Cl or CH3; R6 is H or Cl.
3. The compound according to any one of claims 1 to 2, characterized in that R5 is CH3.
4. The compound according to any one of claims 1 to 3, characterized in that Rs is Cl. 5.The compound according to claim 1, characterized in that it is selected from the group consisting of 6-chloro-4-(2,7-dimethyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone; 6-chloro-4-(7-fluoro-2-methyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2 / - / )-pyridazinone; 6-chloro-4-(7-chloro-2-methyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2 / 7)-pyridazinone; and 6-chloro-4-(4-chloro-2-methyl-1-naphthalenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone. 6.A process for preparing a compound of Formula 1A, 105 ncccnn / i 7P7 / B / Y wherein R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R2 is H or Cl; R5 is H, F, Cl or CH3; and R6 is H or Cl, the process characterized in that it comprises: (1) reacting a compound of Formula II wherein R5 is H, F, Cl or CH3; and R6 is H or Cl with magnesium to form an intermediate compound of Formula III Br A R5 III; and (2) reacting the intermediate compound or the compound of Formula III formed in (1) with a compound of Formula IV-A or IV-B 106 ncccnn / i 7P7 / B / Y wherein R1 is C1-C4 alkyl or Cs-Ce cycloalkyl; G is C1-C4 alkyl, SO2CF3 or SO2(4-Me-Ph). 7.A process for preparing a compound of Formula 1B wherein R1 is C1-C4 alkyl or Cs-Ce cycloalkyl; R5 is H, F, OI or CH3; and R6 is H or Cl, the process being characterized in that it comprises reacting a compound of Formula 1A wherein R1 is C1-C4 alkyl or Ca-Ce cycloalkyl; R2 is H or Cl; R3 is Cl; and R4 is H or Cl; R5 is H, F, Cl or CH3; and R6 is H or Cl with a methoxylating agent.
8. A process for preparing a compound of Formula 1C ncccnn / i 7P7 / B / Y wherein R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R2 is Cl, Bro I; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process characterized in that it comprises: (1) reacting a compound of Formula 1B, as set out in claim 7, with a tmp-zinc base, to form a zinc-plated intermediate compound of Formula V. (2) reacting the zinc-plated intermediate compound of Formula V formed in (1) with a halogenating agent.
9. A process for preparing a compound of Formula lD 108 ncccnn / i 7P7 / B / Y wherein R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R2 is Cl, Bro I; R5 is H, F, Cl or CH3; and R6 is H or Cl, the process characterized in that it comprises reacting a compound of Formula lC, as set forth in claim 8, with a demelting agent.
10. A process for preparing a compound of Formula lE wherein R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl; the process characterized in that it comprises reacting a compound of Formula VI 109 VI ncccnn / i 7P7 / B / Y where R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R5 is H, F, Cl or CH3; and R6 is H or Cl with phosphorus oxychloride. 11.A further process for preparing a compound of Formula IIE wherein R1 is C1-C4 alkyl or C3-Ce cycloalkyl; R5 is H, F, Cl, or CH3; and R6 is H or Cl; the process being characterized in that it comprises: (1) reacting a compound of Formula II II 110 wherein R5 is H, F, Cl, or CH3; and R6 is H or Cl; with magnesium to form an intermediate compound of Formula III ncccnn / i ζπζ / β / υ; and (2) reacting the intermediate compound or Formula III formed in (1) with a compound of Formula 7O wherein R1 is C1-C4 alkyl or Cs-Ce cycloalkyl.
12. A herbicidal composition, characterized in that it comprises the compound according to claim 1 and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents. 13.A herbicidal composition, characterized in that it comprises a compound according to claim 1, at least one additional active ingredient selected from the group consisting of other herbicides and herbicide protectants, and at least one component selected from the group consisting of surfactants, solid diluents, and liquid diluents.
14. A herbicide mixture, characterized in that it comprises (a) a compound according to claim 1, and (b) at least one additional active ingredient.
15. A method for controlling the growth of unwanted vegetation, characterized in that it comprises contacting the vegetation or its surroundings with a herbicidally effective amount of a compound according to claim 1.